 
data_181106_0m
 
_audit_creation_method            SHELXL-2014/6
_chemical_name_systematic         ?
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C19 H22 O6' 
_chemical_formula_weight          346.36

loop_
 _atom_type_symbol
 _atom_type_description
 _atom_type_scat_dispersion_real
 _atom_type_scat_dispersion_imag
 _atom_type_scat_source
 'C'  'C'   0.0033   0.0016
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'H'  'H'   0.0000   0.0000
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'O'  'O'   0.0106   0.0060
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 
_space_group_crystal_system       triclinic
_space_group_IT_number            2
_space_group_name_H-M_alt         'P -1'
_space_group_name_Hall            '-P 1'
 
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
 
loop_
 _space_group_symop_operation_xyz
 'x, y, z'
 '-x, -y, -z'
 
_cell_length_a                    10.0533(5)
_cell_length_b                    10.1641(6)
_cell_length_c                    10.8552(6)
_cell_angle_alpha                 63.909(2)
_cell_angle_beta                  72.068(2)
_cell_angle_gamma                 64.666(2)
_cell_volume                      890.53(9)
_cell_formula_units_Z             2
_cell_measurement_temperature     296(2)
_cell_measurement_reflns_used     4682
_cell_measurement_theta_min       2.3746
_cell_measurement_theta_max       26.1786
 
_exptl_crystal_description        lump
_exptl_crystal_colour             colorless
_exptl_crystal_density_meas       'not measured'
_exptl_crystal_density_method     'not measured'
_exptl_crystal_density_diffrn     1.292          
_exptl_crystal_F_000              368
_exptl_transmission_factor_min    ?
_exptl_transmission_factor_max    ?
_exptl_crystal_size_max           0.20
_exptl_crystal_size_mid           0.15
_exptl_crystal_size_min           0.12
_exptl_absorpt_coefficient_mu     0.096
_shelx_estimated_absorpt_T_min    ?
_shelx_estimated_absorpt_T_max    ?
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.7126  
_exptl_absorpt_correction_T_max   0.7454
_exptl_absorpt_process_details    'SADABS V2014/4 (Bruker AXS Inc.)'
_exptl_absorpt_special_details    ?
_diffrn_ambient_temperature       296(2)
_diffrn_radiation_wavelength      0.71073
_diffrn_radiation_type            MoK\a
_diffrn_source                    ?
_diffrn_measurement_device_type   'Bruker APEX-II CCD'
_diffrn_measurement_method        'φ and ω scans'
_diffrn_detector_area_resol_mean  8.3333
_diffrn_reflns_number             13704
_diffrn_reflns_av_unetI/netI      0.0225
_diffrn_reflns_av_R_equivalents   0.0243
_diffrn_reflns_limit_h_min        -12
_diffrn_reflns_limit_h_max        12
_diffrn_reflns_limit_k_min        -12
_diffrn_reflns_limit_k_max        12
_diffrn_reflns_limit_l_min        -13
_diffrn_reflns_limit_l_max        13
_diffrn_reflns_theta_min          2.112
_diffrn_reflns_theta_max          26.398
_diffrn_reflns_theta_full         25.242
_diffrn_measured_fraction_theta_max   0.999
_diffrn_measured_fraction_theta_full  0.999
_diffrn_reflns_Laue_measured_fraction_max    0.999
_diffrn_reflns_Laue_measured_fraction_full   0.999
_diffrn_reflns_point_group_measured_fraction_max   0.999
_diffrn_reflns_point_group_measured_fraction_full  0.999
_reflns_number_total              3661
_reflns_number_gt                 2924
_reflns_threshold_expression      'I > 2σ(I)'
_reflns_Friedel_coverage          0.000
_reflns_Friedel_fraction_max      .
_reflns_Friedel_fraction_full     .
 
_reflns_special_details
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
 
_computing_data_collection        'Bruker APEX2'
_computing_cell_refinement        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction         'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution     ?
_computing_structure_refinement   'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics     'Bruker SHELXTL'
_computing_publication_material   'Bruker SHELXTL'
_refine_special_details           ?
_refine_ls_structure_factor_coef  Fsqd
_refine_ls_matrix_type            full
_refine_ls_weighting_scheme       calc
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0504P)²+0.1817P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary      ?
_atom_sites_solution_secondary    ?
_atom_sites_solution_hydrogens    geom
_refine_ls_hydrogen_treatment     constr
_refine_ls_extinction_method      none
_refine_ls_extinction_coef        .
_refine_ls_number_reflns          3661
_refine_ls_number_parameters      232
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0516
_refine_ls_R_factor_gt            0.0408
_refine_ls_wR_factor_ref          0.1126
_refine_ls_wR_factor_gt           0.1046
_refine_ls_goodness_of_fit_ref    1.066
_refine_ls_restrained_S_all       1.066
_refine_ls_shift/su_max           0.011
_refine_ls_shift/su_mean          0.000
 
loop_
 _atom_site_label
 _atom_site_type_symbol
 _atom_site_fract_x
 _atom_site_fract_y
 _atom_site_fract_z
 _atom_site_U_iso_or_equiv
 _atom_site_adp_type
 _atom_site_occupancy
 _atom_site_site_symmetry_order  
 _atom_site_calc_flag
 _atom_site_refinement_flags_posn
 _atom_site_refinement_flags_adp
 _atom_site_refinement_flags_occupancy
 _atom_site_disorder_assembly
 _atom_site_disorder_group
O1 O 0.35707(11) 0.36525(12) 0.38709(11) 0.0508(3) Uani 1 1 d . . . . .
O2 O 1.00332(12) -0.10904(13) -0.30075(11) 0.0546(3) Uani 1 1 d . . . . .
O3 O 0.75722(15) -0.33780(13) 0.18671(13) 0.0702(4) Uani 1 1 d . . . . .
O4 O 0.96584(12) 0.17052(12) -0.32954(11) 0.0555(3) Uani 1 1 d . . . . .
O5 O 0.60195(12) 0.12223(13) 0.46371(10) 0.0525(3) Uani 1 1 d . . . . .
O6 O 0.28472(11) 0.47102(11) 0.13737(11) 0.0497(3) Uani 1 1 d . . . . .
C1 C 0.4116(2) 0.4604(2) 0.4087(2) 0.0714(5) Uani 1 1 d . . . . .
H1 H 0.5093 0.4006 0.4345 0.107 Uiso 1 1 calc R U . . .
H16 H 0.3461 0.4967 0.4815 0.107 Uiso 1 1 calc R U . . .
H15 H 0.4161 0.5481 0.3248 0.107 Uiso 1 1 calc R U . . .
C2 C 0.45076(14) 0.29463(15) 0.29407(14) 0.0372(3) Uani 1 1 d . . . . .
C3 C 0.57810(15) 0.16546(16) 0.33277(14) 0.0372(3) Uani 1 1 d . . . . .
C4 C 0.66856(14) 0.09100(15) 0.24020(14) 0.0367(3) Uani 1 1 d . . . . .
H21 H 0.7546 0.0064 0.2654 0.044 Uiso 1 1 calc R U . . .
C5 C 0.63064(14) 0.14265(15) 0.11038(14) 0.0344(3) Uani 1 1 d . . . . .
C6 C 0.72827(14) 0.06475(15) 0.00895(14) 0.0345(3) Uani 1 1 d . . . . .
C7 C 0.75581(14) -0.08952(15) 0.02903(14) 0.0357(3) Uani 1 1 d . . . . .
C8 C 0.85102(15) -0.14967(15) -0.07403(15) 0.0388(3) Uani 1 1 d . . . . .
H4 H 0.8705 -0.2528 -0.0602 0.047 Uiso 1 1 calc R U . . .
C9 C 0.91587(14) -0.06153(16) -0.19369(15) 0.0394(3) Uani 1 1 d . . . . .
C10 C 1.0255(2) -0.25973(19) -0.29318(18) 0.0632(5) Uani 1 1 d . . . . .
H22 H 1.0819 -0.3371 -0.2197 0.095 Uiso 1 1 calc R U . . .
H2 H 1.0789 -0.2725 -0.3796 0.095 Uiso 1 1 calc R U . . .
H3 H 0.9309 -0.2716 -0.2752 0.095 Uiso 1 1 calc R U . . .
C11 C 0.68796(17) -0.19872(16) 0.15003(15) 0.0432(3) Uani 1 1 d . . . . .
C12 C 0.53227(18) -0.1407(2) 0.22002(17) 0.0535(4) Uani 1 1 d . . . . .
H6 H 0.4821 -0.2114 0.2403 0.080 Uiso 1 1 calc R U . . .
H5 H 0.4799 -0.0393 0.1599 0.080 Uiso 1 1 calc R U . . .
H7 H 0.5351 -0.1343 0.3048 0.080 Uiso 1 1 calc R U . . .
C13 C 0.79902(14) 0.15246(15) -0.11147(14) 0.0385(3) Uani 1 1 d . . . . .
H11 H 0.7825 0.2547 -0.1246 0.046 Uiso 1 1 calc R U . . .
C14 C 0.89258(15) 0.09186(16) -0.21135(15) 0.0394(3) Uani 1 1 d . . . . .
C15 C 0.97957(19) 0.30734(19) -0.3356(2) 0.0626(5) Uani 1 1 d . . . . .
H8 H 0.8838 0.3882 -0.3394 0.094 Uiso 1 1 calc R U . . .
H9 H 1.0468 0.3415 -0.4170 0.094 Uiso 1 1 calc R U . . .
H10 H 1.0173 0.2844 -0.2546 0.094 Uiso 1 1 calc R U . . .
C16 C 0.72240(17) -0.01584(19) 0.51501(16) 0.0532(4) Uani 1 1 d . . . . .
H12 H 0.7123 -0.1018 0.5076 0.080 Uiso 1 1 calc R U . . .
H13 H 0.7217 -0.0368 0.6104 0.080 Uiso 1 1 calc R U . . .
H14 H 0.8145 -0.0023 0.4616 0.080 Uiso 1 1 calc R U . . .
C17 C 0.41322(14) 0.34607(15) 0.16370(15) 0.0366(3) Uani 1 1 d . . . . .
C18 C 0.24102(18) 0.53185(18) 0.00476(18) 0.0519(4) Uani 1 1 d . . . . .
H18 H 0.3166 0.5666 -0.0657 0.078 Uiso 1 1 calc R U . . .
H19 H 0.1491 0.6181 0.0004 0.078 Uiso 1 1 calc R U . . .
H17 H 0.2278 0.4520 -0.0100 0.078 Uiso 1 1 calc R U . . .
C19 C 0.50304(14) 0.27083(15) 0.07150(14) 0.0364(3) Uani 1 1 d . . . . .
H20 H 0.4781 0.3059 -0.0160 0.044 Uiso 1 1 calc R U . . .
 
 
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
 
loop_
 _geom_bond_atom_site_label_1
 _geom_bond_atom_site_label_2
 _geom_bond_distance
 _geom_bond_site_symmetry_2
 _geom_bond_publ_flag
O1 C2 1.3767(15) . ?
O1 C1 1.423(2) . ?
O2 C9 1.3630(16) . ?
O2 C10 1.4178(19) . ?
O3 C11 1.2145(17) . ?
O4 C14 1.3592(17) . ?
O4 C15 1.4266(19) . ?
O5 C3 1.3569(17) . ?
O5 C16 1.4211(18) . ?
O6 C17 1.3665(15) . ?
O6 C18 1.4218(18) . ?
C1 H1 0.9600 . ?
C1 H16 0.9600 . ?
C1 H15 0.9600 . ?
C2 C17 1.388(2) . ?
C2 C3 1.3953(19) . ?
C3 C4 1.3880(18) . ?
C4 C5 1.3841(19) . ?
C4 H21 0.9300 . ?
C5 C19 1.3930(17) . ?
C5 C6 1.4963(17) . ?
C6 C7 1.3957(18) . ?
C6 C13 1.3980(19) . ?
C7 C8 1.4082(18) . ?
C7 C11 1.495(2) . ?
C8 C9 1.367(2) . ?
C8 H4 0.9300 . ?
C9 C14 1.4052(19) . ?
C10 H22 0.9600 . ?
C10 H2 0.9600 . ?
C10 H3 0.9600 . ?
C11 C12 1.499(2) . ?
C12 H6 0.9600 . ?
C12 H5 0.9600 . ?
C12 H7 0.9600 . ?
C13 C14 1.3795(18) . ?
C13 H11 0.9300 . ?
C15 H8 0.9600 . ?
C15 H9 0.9600 . ?
C15 H10 0.9600 . ?
C16 H12 0.9600 . ?
C16 H13 0.9600 . ?
C16 H14 0.9600 . ?
C17 C19 1.3885(18) . ?
C18 H18 0.9600 . ?
C18 H19 0.9600 . ?
C18 H17 0.9600 . ?
C19 H20 0.9300 . ?
 
loop_
 _geom_angle_atom_site_label_1
 _geom_angle_atom_site_label_2
 _geom_angle_atom_site_label_3
 _geom_angle
 _geom_angle_site_symmetry_1
 _geom_angle_site_symmetry_3
 _geom_angle_publ_flag
C2 O1 C1 114.10(12) . . ?
C9 O2 C10 118.62(12) . . ?
C14 O4 C15 117.87(12) . . ?
C3 O5 C16 118.26(11) . . ?
C17 O6 C18 118.03(11) . . ?
O1 C1 H1 109.5 . . ?
O1 C1 H16 109.5 . . ?
H1 C1 H16 109.5 . . ?
O1 C1 H15 109.5 . . ?
H1 C1 H15 109.5 . . ?
H16 C1 H15 109.5 . . ?
O1 C2 C17 119.67(12) . . ?
O1 C2 C3 120.53(12) . . ?
C17 C2 C3 119.66(11) . . ?
O5 C3 C4 125.04(12) . . ?
O5 C3 C2 114.82(11) . . ?
C4 C3 C2 120.13(12) . . ?
C5 C4 C3 119.99(12) . . ?
C5 C4 H21 120.0 . . ?
C3 C4 H21 120.0 . . ?
C4 C5 C19 120.15(11) . . ?
C4 C5 C6 120.51(11) . . ?
C19 C5 C6 119.32(12) . . ?
C7 C6 C13 118.61(11) . . ?
C7 C6 C5 124.28(12) . . ?
C13 C6 C5 117.08(11) . . ?
C6 C7 C8 118.80(12) . . ?
C6 C7 C11 125.70(12) . . ?
C8 C7 C11 115.45(11) . . ?
C9 C8 C7 122.23(12) . . ?
C9 C8 H4 118.9 . . ?
C7 C8 H4 118.9 . . ?
O2 C9 C8 125.62(12) . . ?
O2 C9 C14 115.52(12) . . ?
C8 C9 C14 118.86(12) . . ?
O2 C10 H22 109.5 . . ?
O2 C10 H2 109.5 . . ?
H22 C10 H2 109.5 . . ?
O2 C10 H3 109.5 . . ?
H22 C10 H3 109.5 . . ?
H2 C10 H3 109.5 . . ?
O3 C11 C7 119.20(13) . . ?
O3 C11 C12 119.50(14) . . ?
C7 C11 C12 121.16(13) . . ?
C11 C12 H6 109.5 . . ?
C11 C12 H5 109.5 . . ?
H6 C12 H5 109.5 . . ?
C11 C12 H7 109.5 . . ?
H6 C12 H7 109.5 . . ?
H5 C12 H7 109.5 . . ?
C14 C13 C6 121.99(12) . . ?
C14 C13 H11 119.0 . . ?
C6 C13 H11 119.0 . . ?
O4 C14 C13 124.72(12) . . ?
O4 C14 C9 115.86(12) . . ?
C13 C14 C9 119.42(12) . . ?
O4 C15 H8 109.5 . . ?
O4 C15 H9 109.5 . . ?
H8 C15 H9 109.5 . . ?
O4 C15 H10 109.5 . . ?
H8 C15 H10 109.5 . . ?
H9 C15 H10 109.5 . . ?
O5 C16 H12 109.5 . . ?
O5 C16 H13 109.5 . . ?
H12 C16 H13 109.5 . . ?
O5 C16 H14 109.5 . . ?
H12 C16 H14 109.5 . . ?
H13 C16 H14 109.5 . . ?
O6 C17 C2 115.00(11) . . ?
O6 C17 C19 124.79(12) . . ?
C2 C17 C19 120.21(12) . . ?
O6 C18 H18 109.5 . . ?
O6 C18 H19 109.5 . . ?
H18 C18 H19 109.5 . . ?
O6 C18 H17 109.5 . . ?
H18 C18 H17 109.5 . . ?
H19 C18 H17 109.5 . . ?
C17 C19 C5 119.85(12) . . ?
C17 C19 H20 120.1 . . ?
C5 C19 H20 120.1 . . ?
 
_refine_diff_density_max    0.163
_refine_diff_density_min   -0.171
_refine_diff_density_rms    0.036

_shelxl_version_number 2014/6



 
data_180611LT_0m
 
_audit_creation_method            SHELXL-2014/6
_chemical_name_systematic         ?
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C23 H22 O5 S' 
_chemical_formula_weight          410.46

loop_
 _atom_type_symbol
 _atom_type_description
 _atom_type_scat_dispersion_real
 _atom_type_scat_dispersion_imag
 _atom_type_scat_source
 'C'  'C'   0.0033   0.0016
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'H'  'H'   0.0000   0.0000
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'O'  'O'   0.0106   0.0060
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'S'  'S'   0.1246   0.1234
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 
_space_group_crystal_system       triclinic
_space_group_IT_number            2
_space_group_name_H-M_alt         'P -1'
_space_group_name_Hall            '-P 1'
 
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
 
loop_
 _space_group_symop_operation_xyz
 'x, y, z'
 '-x, -y, -z'
 
_cell_length_a                    7.9278(10)
_cell_length_b                    8.4094(10)
_cell_length_c                    15.9103(19)
_cell_angle_alpha                 81.239(6)
_cell_angle_beta                  78.859(6)
_cell_angle_gamma                 75.503(6)
_cell_volume                      1001.5(2)
_cell_formula_units_Z             2
_cell_measurement_temperature     100(2)
_cell_measurement_reflns_used     8757
_cell_measurement_theta_min       2.5167
_cell_measurement_theta_max       26.3880
 
_exptl_crystal_description        lump
_exptl_crystal_colour             colorless
_exptl_crystal_density_meas       'not measured'
_exptl_crystal_density_method     'not measured'
_exptl_crystal_density_diffrn     1.361          
_exptl_crystal_F_000              432
_exptl_transmission_factor_min    ?
_exptl_transmission_factor_max    ?
_exptl_crystal_size_max           0.20
_exptl_crystal_size_mid           0.15
_exptl_crystal_size_min           0.15
_exptl_absorpt_coefficient_mu     0.194
_shelx_estimated_absorpt_T_min    ?
_shelx_estimated_absorpt_T_max    ?
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.8375  
_exptl_absorpt_correction_T_max   0.9705
_exptl_absorpt_process_details    'SADABS V2014/4 (Bruker AXS Inc.)'
_exptl_absorpt_special_details    ?
_diffrn_ambient_temperature       100(2)
_diffrn_radiation_wavelength      0.71073
_diffrn_radiation_type            MoK\a
_diffrn_source                    ?
_diffrn_measurement_device_type   'Bruker APEX-II CCD'
_diffrn_measurement_method        'φ and ω scans'
_diffrn_detector_area_resol_mean  8.3333
_diffrn_reflns_number             15223
_diffrn_reflns_av_unetI/netI      0.0274
_diffrn_reflns_av_R_equivalents   0.0298
_diffrn_reflns_limit_h_min        -9
_diffrn_reflns_limit_h_max        9
_diffrn_reflns_limit_k_min        -10
_diffrn_reflns_limit_k_max        10
_diffrn_reflns_limit_l_min        -19
_diffrn_reflns_limit_l_max        17
_diffrn_reflns_theta_min          1.312
_diffrn_reflns_theta_max          26.461
_diffrn_reflns_theta_full         25.242
_diffrn_measured_fraction_theta_max   0.990
_diffrn_measured_fraction_theta_full  0.996
_diffrn_reflns_Laue_measured_fraction_max    0.990
_diffrn_reflns_Laue_measured_fraction_full   0.996
_diffrn_reflns_point_group_measured_fraction_max   0.990
_diffrn_reflns_point_group_measured_fraction_full  0.996
_reflns_number_total              4082
_reflns_number_gt                 3667
_reflns_threshold_expression      'I > 2σ(I)'
_reflns_Friedel_coverage          0.000
_reflns_Friedel_fraction_max      .
_reflns_Friedel_fraction_full     .
 
_reflns_special_details
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
 
_computing_data_collection        'Bruker APEX2'
_computing_cell_refinement        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction         'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution     ?
_computing_structure_refinement   'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics     'Bruker SHELXTL'
_computing_publication_material   'Bruker SHELXTL'
_refine_special_details           ?
_refine_ls_structure_factor_coef  Fsqd
_refine_ls_matrix_type            full
_refine_ls_weighting_scheme       calc
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0454P)²+0.4731P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary      ?
_atom_sites_solution_secondary    ?
_atom_sites_solution_hydrogens    geom
_refine_ls_hydrogen_treatment     constr
_refine_ls_extinction_method      none
_refine_ls_extinction_coef        .
_refine_ls_number_reflns          4082
_refine_ls_number_parameters      265
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0397
_refine_ls_R_factor_gt            0.0354
_refine_ls_wR_factor_ref          0.0952
_refine_ls_wR_factor_gt           0.0920
_refine_ls_goodness_of_fit_ref    1.061
_refine_ls_restrained_S_all       1.061
_refine_ls_shift/su_max           0.002
_refine_ls_shift/su_mean          0.000
 
loop_
 _atom_site_label
 _atom_site_type_symbol
 _atom_site_fract_x
 _atom_site_fract_y
 _atom_site_fract_z
 _atom_site_U_iso_or_equiv
 _atom_site_adp_type
 _atom_site_occupancy
 _atom_site_site_symmetry_order  
 _atom_site_calc_flag
 _atom_site_refinement_flags_posn
 _atom_site_refinement_flags_adp
 _atom_site_refinement_flags_occupancy
 _atom_site_disorder_assembly
 _atom_site_disorder_group
S1 S 0.31039(4) 0.77912(4) 0.81685(2) 0.01820(11) Uani 1 1 d . . . . .
O1 O 0.74910(14) 1.20523(12) 0.47306(7) 0.0222(2) Uani 1 1 d . . . . .
O2 O 0.18742(14) 0.93742(14) 0.81496(7) 0.0278(3) Uani 1 1 d . . . . .
O3 O 0.24771(14) 0.63312(14) 0.85286(7) 0.0257(3) Uani 1 1 d . . . . .
O4 O 0.43986(13) 0.48443(13) 0.67558(7) 0.0238(2) Uani 1 1 d . . . . .
O5 O 0.69720(14) 0.94622(12) 0.42528(7) 0.0202(2) Uani 1 1 d . . . . .
C1 C 0.8923(2) 0.8147(2) 1.00429(11) 0.0336(4) Uani 1 1 d . . . . .
H22 H 0.9475 0.7033 1.0279 0.050 Uiso 1 1 calc R U . . .
H3 H 0.8419 0.8839 1.0514 0.050 Uiso 1 1 calc R U . . .
H1 H 0.9813 0.8629 0.9642 0.050 Uiso 1 1 calc R U . . .
C2 C 0.7482(2) 0.8052(2) 0.95730(10) 0.0247(3) Uani 1 1 d . . . . .
C3 C 0.6990(2) 0.6571(2) 0.95924(10) 0.0254(3) Uani 1 1 d . . . . .
H4 H 0.7578 0.5603 0.9904 0.031 Uiso 1 1 calc R U . . .
C4 C 0.5656(2) 0.64820(19) 0.91647(10) 0.0226(3) Uani 1 1 d . . . . .
H5 H 0.5332 0.5463 0.9181 0.027 Uiso 1 1 calc R U . . .
C5 C 0.48004(18) 0.78996(18) 0.87119(9) 0.0182(3) Uani 1 1 d . . . . .
C6 C 0.41288(18) 0.75575(17) 0.70776(9) 0.0167(3) Uani 1 1 d . . . . .
H6 H 0.3212 0.7883 0.6701 0.020 Uiso 1 1 calc R U . . .
H7 H 0.4949 0.8307 0.6896 0.020 Uiso 1 1 calc R U . . .
C7 C 0.51421(18) 0.57932(17) 0.69622(9) 0.0165(3) Uani 1 1 d . . . . .
C8 C 0.69610(18) 0.52072(17) 0.71804(9) 0.0163(3) Uani 1 1 d . . . . .
C9 C 0.82525(18) 0.61541(17) 0.69908(9) 0.0169(3) Uani 1 1 d . . . . .
C10 C 0.80597(17) 0.77323(17) 0.64163(9) 0.0167(3) Uani 1 1 d . . . . .
C11 C 0.84253(19) 0.91192(18) 0.66516(10) 0.0197(3) Uani 1 1 d . . . . .
H17 H 0.8801 0.9065 0.7189 0.024 Uiso 1 1 calc R U . . .
C12 C 0.82443(19) 1.05885(18) 0.61039(10) 0.0201(3) Uani 1 1 d . . . . .
H18 H 0.8476 1.1536 0.6276 0.024 Uiso 1 1 calc R U . . .
C13 C 0.77311(18) 1.06791(17) 0.53125(9) 0.0178(3) Uani 1 1 d . . . . .
C14 C 0.7687(2) 1.35461(17) 0.49845(11) 0.0233(3) Uani 1 1 d . . . . .
H15 H 0.6865 1.3804 0.5517 0.035 Uiso 1 1 calc R U . . .
H16 H 0.7429 1.4452 0.4528 0.035 Uiso 1 1 calc R U . . .
H2 H 0.8900 1.3408 0.5083 0.035 Uiso 1 1 calc R U . . .
C15 C 0.98272(19) 0.55187(19) 0.73135(10) 0.0222(3) Uani 1 1 d . . . . .
H11 H 1.0699 0.6153 0.7203 0.027 Uiso 1 1 calc R U . . .
C16 C 1.0155(2) 0.3987(2) 0.77911(10) 0.0255(3) Uani 1 1 d . . . . .
H10 H 1.1231 0.3593 0.8014 0.031 Uiso 1 1 calc R U . . .
C17 C 0.8912(2) 0.30263(19) 0.79444(10) 0.0244(3) Uani 1 1 d . . . . .
H9 H 0.9150 0.1957 0.8254 0.029 Uiso 1 1 calc R U . . .
C18 C 0.73272(19) 0.36402(18) 0.76420(10) 0.0204(3) Uani 1 1 d . . . . .
H8 H 0.6473 0.2987 0.7749 0.025 Uiso 1 1 calc R U . . .
C19 C 0.75596(17) 0.78197(17) 0.56074(9) 0.0161(3) Uani 1 1 d . . . . .
H19 H 0.7322 0.6872 0.5439 0.019 Uiso 1 1 calc R U . . .
C20 C 0.74085(18) 0.92618(17) 0.50546(9) 0.0163(3) Uani 1 1 d . . . . .
C21 C 0.6803(2) 0.80258(18) 0.39320(10) 0.0239(3) Uani 1 1 d . . . . .
H12 H 0.7911 0.7185 0.3930 0.036 Uiso 1 1 calc R U . . .
H14 H 0.6539 0.8315 0.3344 0.036 Uiso 1 1 calc R U . . .
H13 H 0.5843 0.7591 0.4302 0.036 Uiso 1 1 calc R U . . .
C22 C 0.5267(2) 0.93952(19) 0.86819(10) 0.0234(3) Uani 1 1 d . . . . .
H21 H 0.4680 1.0361 0.8368 0.028 Uiso 1 1 calc R U . . .
C23 C 0.6597(2) 0.9460(2) 0.91153(11) 0.0267(3) Uani 1 1 d . . . . .
H20 H 0.6913 1.0482 0.9101 0.032 Uiso 1 1 calc R U . . .
 
 
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
 
loop_
 _geom_bond_atom_site_label_1
 _geom_bond_atom_site_label_2
 _geom_bond_distance
 _geom_bond_site_symmetry_2
 _geom_bond_publ_flag
S1 O3 1.4366(11) . ?
S1 O2 1.4397(11) . ?
S1 C5 1.7606(15) . ?
S1 C6 1.7862(14) . ?
O1 C13 1.3636(17) . ?
O1 C14 1.4289(16) . ?
O4 C7 1.2174(17) . ?
O5 C20 1.3607(17) . ?
O5 C21 1.4258(17) . ?
C1 C2 1.504(2) . ?
C1 H22 0.9800 . ?
C1 H3 0.9800 . ?
C1 H1 0.9800 . ?
C2 C3 1.390(2) . ?
C2 C23 1.394(2) . ?
C3 C4 1.386(2) . ?
C3 H4 0.9500 . ?
C4 C5 1.387(2) . ?
C4 H5 0.9500 . ?
C5 C22 1.389(2) . ?
C6 C7 1.5197(19) . ?
C6 H6 0.9900 . ?
C6 H7 0.9900 . ?
C7 C8 1.4927(19) . ?
C8 C18 1.399(2) . ?
C8 C9 1.4103(19) . ?
C9 C15 1.392(2) . ?
C9 C10 1.484(2) . ?
C10 C11 1.3887(19) . ?
C10 C19 1.405(2) . ?
C11 C12 1.392(2) . ?
C11 H17 0.9500 . ?
C12 C13 1.382(2) . ?
C12 H18 0.9500 . ?
C13 C20 1.4129(19) . ?
C14 H15 0.9800 . ?
C14 H16 0.9800 . ?
C14 H2 0.9800 . ?
C15 C16 1.384(2) . ?
C15 H11 0.9500 . ?
C16 C17 1.389(2) . ?
C16 H10 0.9500 . ?
C17 C18 1.382(2) . ?
C17 H9 0.9500 . ?
C18 H8 0.9500 . ?
C19 C20 1.379(2) . ?
C19 H19 0.9500 . ?
C21 H12 0.9800 . ?
C21 H14 0.9800 . ?
C21 H13 0.9800 . ?
C22 C23 1.382(2) . ?
C22 H21 0.9500 . ?
C23 H20 0.9500 . ?
 
loop_
 _geom_angle_atom_site_label_1
 _geom_angle_atom_site_label_2
 _geom_angle_atom_site_label_3
 _geom_angle
 _geom_angle_site_symmetry_1
 _geom_angle_site_symmetry_3
 _geom_angle_publ_flag
O3 S1 O2 119.44(7) . . ?
O3 S1 C5 108.38(7) . . ?
O2 S1 C5 108.05(7) . . ?
O3 S1 C6 108.59(7) . . ?
O2 S1 C6 106.07(7) . . ?
C5 S1 C6 105.47(7) . . ?
C13 O1 C14 116.96(11) . . ?
C20 O5 C21 117.03(11) . . ?
C2 C1 H22 109.5 . . ?
C2 C1 H3 109.5 . . ?
H22 C1 H3 109.5 . . ?
C2 C1 H1 109.5 . . ?
H22 C1 H1 109.5 . . ?
H3 C1 H1 109.5 . . ?
C3 C2 C23 118.53(14) . . ?
C3 C2 C1 120.99(15) . . ?
C23 C2 C1 120.48(15) . . ?
C4 C3 C2 121.12(15) . . ?
C4 C3 H4 119.4 . . ?
C2 C3 H4 119.4 . . ?
C3 C4 C5 119.18(14) . . ?
C3 C4 H5 120.4 . . ?
C5 C4 H5 120.4 . . ?
C4 C5 C22 120.87(14) . . ?
C4 C5 S1 119.29(11) . . ?
C22 C5 S1 119.84(11) . . ?
C7 C6 S1 112.09(10) . . ?
C7 C6 H6 109.2 . . ?
S1 C6 H6 109.2 . . ?
C7 C6 H7 109.2 . . ?
S1 C6 H7 109.2 . . ?
H6 C6 H7 107.9 . . ?
O4 C7 C8 120.95(13) . . ?
O4 C7 C6 118.95(12) . . ?
C8 C7 C6 119.86(12) . . ?
C18 C8 C9 119.65(13) . . ?
C18 C8 C7 115.86(12) . . ?
C9 C8 C7 124.41(12) . . ?
C15 C9 C8 118.12(13) . . ?
C15 C9 C10 118.68(12) . . ?
C8 C9 C10 123.07(12) . . ?
C11 C10 C19 119.04(13) . . ?
C11 C10 C9 121.08(13) . . ?
C19 C10 C9 119.85(12) . . ?
C10 C11 C12 120.37(13) . . ?
C10 C11 H17 119.8 . . ?
C12 C11 H17 119.8 . . ?
C13 C12 C11 120.53(13) . . ?
C13 C12 H18 119.7 . . ?
C11 C12 H18 119.7 . . ?
O1 C13 C12 125.60(13) . . ?
O1 C13 C20 114.80(12) . . ?
C12 C13 C20 119.60(13) . . ?
O1 C14 H15 109.5 . . ?
O1 C14 H16 109.5 . . ?
H15 C14 H16 109.5 . . ?
O1 C14 H2 109.5 . . ?
H15 C14 H2 109.5 . . ?
H16 C14 H2 109.5 . . ?
C16 C15 C9 121.70(14) . . ?
C16 C15 H11 119.2 . . ?
C9 C15 H11 119.2 . . ?
C15 C16 C17 120.02(14) . . ?
C15 C16 H10 120.0 . . ?
C17 C16 H10 120.0 . . ?
C18 C17 C16 119.36(14) . . ?
C18 C17 H9 120.3 . . ?
C16 C17 H9 120.3 . . ?
C17 C18 C8 121.06(14) . . ?
C17 C18 H8 119.5 . . ?
C8 C18 H8 119.5 . . ?
C20 C19 C10 120.93(12) . . ?
C20 C19 H19 119.5 . . ?
C10 C19 H19 119.5 . . ?
O5 C20 C19 125.43(12) . . ?
O5 C20 C13 115.09(12) . . ?
C19 C20 C13 119.48(13) . . ?
O5 C21 H12 109.5 . . ?
O5 C21 H14 109.5 . . ?
H12 C21 H14 109.5 . . ?
O5 C21 H13 109.5 . . ?
H12 C21 H13 109.5 . . ?
H14 C21 H13 109.5 . . ?
C23 C22 C5 119.08(14) . . ?
C23 C22 H21 120.5 . . ?
C5 C22 H21 120.5 . . ?
C22 C23 C2 121.22(14) . . ?
C22 C23 H20 119.4 . . ?
C2 C23 H20 119.4 . . ?
 
_refine_diff_density_max    0.347
_refine_diff_density_min   -0.452
_refine_diff_density_rms    0.069

_shelxl_version_number 2014/6



 
data_mo_180844LT_0m
 
_audit_creation_method            SHELXL-2014/6
_chemical_name_systematic         ?
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C17 H16 O4 S' 
_chemical_formula_weight          316.36

loop_
 _atom_type_symbol
 _atom_type_description
 _atom_type_scat_dispersion_real
 _atom_type_scat_dispersion_imag
 _atom_type_scat_source
 'C'  'C'   0.0033   0.0016
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'H'  'H'   0.0000   0.0000
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'O'  'O'   0.0106   0.0060
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'S'  'S'   0.1246   0.1234
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 
_space_group_crystal_system       triclinic
_space_group_IT_number            2
_space_group_name_H-M_alt         'P -1'
_space_group_name_Hall            '-P 1'
 
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
 
loop_
 _space_group_symop_operation_xyz
 'x, y, z'
 '-x, -y, -z'
 
_cell_length_a                    8.5546(2)
_cell_length_b                    9.0687(2)
_cell_length_c                    9.9760(2)
_cell_angle_alpha                 85.8850(10)
_cell_angle_beta                  73.7530(10)
_cell_angle_gamma                 86.5520(10)
_cell_volume                      740.46(3)
_cell_formula_units_Z             2
_cell_measurement_temperature     100(2)
_cell_measurement_reflns_used     8575
_cell_measurement_theta_min       2.2535
_cell_measurement_theta_max       26.3675
 
_exptl_crystal_description        Lump
_exptl_crystal_colour             Red
_exptl_crystal_density_meas       'not measured'
_exptl_crystal_density_method     'not measured'
_exptl_crystal_density_diffrn     1.419          
_exptl_crystal_F_000              332
_exptl_transmission_factor_min    ?
_exptl_transmission_factor_max    ?
_exptl_crystal_size_max           0.18
_exptl_crystal_size_mid           0.15
_exptl_crystal_size_min           0.12
_exptl_absorpt_coefficient_mu     0.234
_shelx_estimated_absorpt_T_min    ?
_shelx_estimated_absorpt_T_max    ?
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.6954  
_exptl_absorpt_correction_T_max   0.7454
_exptl_absorpt_process_details    'SADABS V2014/4 (Bruker AXS Inc.)'
_exptl_absorpt_special_details    ?
_diffrn_ambient_temperature       100(2)
_diffrn_radiation_wavelength      0.71073
_diffrn_radiation_type            MoK\a
_diffrn_source                    ?
_diffrn_measurement_device_type   'Bruker APEX-II CCD'
_diffrn_measurement_method        'φ and ω scans'
_diffrn_detector_area_resol_mean  8.3333
_diffrn_reflns_number             15867
_diffrn_reflns_av_unetI/netI      0.0166
_diffrn_reflns_av_R_equivalents   0.0205
_diffrn_reflns_limit_h_min        -10
_diffrn_reflns_limit_h_max        10
_diffrn_reflns_limit_k_min        -11
_diffrn_reflns_limit_k_max        11
_diffrn_reflns_limit_l_min        -12
_diffrn_reflns_limit_l_max        12
_diffrn_reflns_theta_min          2.254
_diffrn_reflns_theta_max          26.410
_diffrn_reflns_theta_full         25.242
_diffrn_measured_fraction_theta_max   0.995
_diffrn_measured_fraction_theta_full  0.995
_diffrn_reflns_Laue_measured_fraction_max    0.995
_diffrn_reflns_Laue_measured_fraction_full   0.995
_diffrn_reflns_point_group_measured_fraction_max   0.995
_diffrn_reflns_point_group_measured_fraction_full  0.995
_reflns_number_total              3025
_reflns_number_gt                 2743
_reflns_threshold_expression      'I > 2σ(I)'
_reflns_Friedel_coverage          0.000
_reflns_Friedel_fraction_max      .
_reflns_Friedel_fraction_full     .
 
_reflns_special_details
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
 
_computing_data_collection        'Bruker APEX2'
_computing_cell_refinement        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction         'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution     ?
_computing_structure_refinement   'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics     'Bruker SHELXTL'
_computing_publication_material   'Bruker SHELXTL'
_refine_special_details           ?
_refine_ls_structure_factor_coef  Fsqd
_refine_ls_matrix_type            full
_refine_ls_weighting_scheme       calc
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0431P)²+0.4445P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary      ?
_atom_sites_solution_secondary    ?
_atom_sites_solution_hydrogens    geom
_refine_ls_hydrogen_treatment     constr
_refine_ls_extinction_method      none
_refine_ls_extinction_coef        .
_refine_ls_number_reflns          3025
_refine_ls_number_parameters      202
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0348
_refine_ls_R_factor_gt            0.0312
_refine_ls_wR_factor_ref          0.0860
_refine_ls_wR_factor_gt           0.0833
_refine_ls_goodness_of_fit_ref    1.059
_refine_ls_restrained_S_all       1.059
_refine_ls_shift/su_max           0.000
_refine_ls_shift/su_mean          0.000
 
loop_
 _atom_site_label
 _atom_site_type_symbol
 _atom_site_fract_x
 _atom_site_fract_y
 _atom_site_fract_z
 _atom_site_U_iso_or_equiv
 _atom_site_adp_type
 _atom_site_occupancy
 _atom_site_site_symmetry_order  
 _atom_site_calc_flag
 _atom_site_refinement_flags_posn
 _atom_site_refinement_flags_adp
 _atom_site_refinement_flags_occupancy
 _atom_site_disorder_assembly
 _atom_site_disorder_group
S1 S 0.55538(4) 0.67399(4) 0.77229(3) 0.01462(11) Uani 1 1 d . . . . .
O1 O -0.40066(12) 0.70893(11) 1.24824(11) 0.0204(2) Uani 1 1 d . . . . .
O2 O -0.17795(12) 0.54038(11) 1.31213(10) 0.0184(2) Uani 1 1 d . . . . .
O3 O 0.65444(12) 0.56406(12) 0.82619(11) 0.0228(2) Uani 1 1 d . . . . .
O4 O 0.60795(12) 0.82404(11) 0.75038(11) 0.0203(2) Uani 1 1 d . . . . .
C1 C 0.53793(18) 0.61419(16) 0.61326(14) 0.0189(3) Uani 1 1 d . . . . .
H1 H 0.6447 0.6157 0.5438 0.028 Uiso 1 1 calc R U . . .
H3 H 0.4603 0.6803 0.5797 0.028 Uiso 1 1 calc R U . . .
H16 H 0.4991 0.5132 0.6278 0.028 Uiso 1 1 calc R U . . .
C2 C 0.36025(16) 0.66620(15) 0.88844(14) 0.0143(3) Uani 1 1 d . . . . .
H15 H 0.3474 0.5938 0.9640 0.017 Uiso 1 1 calc R U . . .
C3 C 0.22623(16) 0.74938(15) 0.88454(14) 0.0136(3) Uani 1 1 d . . . . .
C4 C 0.06848(16) 0.72611(15) 0.99019(14) 0.0140(3) Uani 1 1 d . . . . .
C5 C 0.03282(16) 0.62937(15) 1.10872(14) 0.0147(3) Uani 1 1 d . . . . .
H4 H 0.1154 0.5661 1.1315 0.018 Uiso 1 1 calc R U . . .
C6 C -0.12632(17) 0.62822(15) 1.19213(14) 0.0150(3) Uani 1 1 d . . . . .
C7 C -0.24937(16) 0.72146(15) 1.15691(15) 0.0160(3) Uani 1 1 d . . . . .
C8 C -0.53115(17) 0.79628(18) 1.21548(17) 0.0238(3) Uani 1 1 d . . . . .
H9 H -0.5083 0.9014 1.2113 0.036 Uiso 1 1 calc R U . . .
H8 H -0.6330 0.7769 1.2879 0.036 Uiso 1 1 calc R U . . .
H2 H -0.5416 0.7705 1.1247 0.036 Uiso 1 1 calc R U . . .
C9 C -0.05808(18) 0.44087(16) 1.34724(15) 0.0191(3) Uani 1 1 d . . . . .
H6 H -0.0095 0.3778 1.2692 0.029 Uiso 1 1 calc R U . . .
H7 H -0.1094 0.3790 1.4309 0.029 Uiso 1 1 calc R U . . .
H5 H 0.0270 0.4974 1.3658 0.029 Uiso 1 1 calc R U . . .
C10 C -0.21279(17) 0.81606(15) 1.03816(15) 0.0163(3) Uani 1 1 d . . . . .
H14 H -0.2952 0.8782 1.0137 0.020 Uiso 1 1 calc R U . . .
C11 C -0.05206(17) 0.81784(15) 0.95546(14) 0.0147(3) Uani 1 1 d . . . . .
C12 C 0.02288(17) 0.90582(15) 0.82677(14) 0.0151(3) Uani 1 1 d . . . . .
C13 C 0.19180(16) 0.86785(15) 0.78403(14) 0.0142(3) Uani 1 1 d . . . . .
C14 C 0.28977(17) 0.93787(15) 0.66438(15) 0.0169(3) Uani 1 1 d . . . . .
H13 H 0.4037 0.9153 0.6357 0.020 Uiso 1 1 calc R U . . .
C15 C 0.21889(18) 1.04191(16) 0.58671(15) 0.0198(3) Uani 1 1 d . . . . .
H12 H 0.2849 1.0891 0.5038 0.024 Uiso 1 1 calc R U . . .
C16 C 0.05300(19) 1.07711(16) 0.62932(16) 0.0210(3) Uani 1 1 d . . . . .
H11 H 0.0068 1.1483 0.5753 0.025 Uiso 1 1 calc R U . . .
C17 C -0.04649(18) 1.00963(16) 0.74997(15) 0.0188(3) Uani 1 1 d . . . . .
H10 H -0.1600 1.0344 0.7791 0.023 Uiso 1 1 calc R U . . .
 
 
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
 
loop_
 _geom_bond_atom_site_label_1
 _geom_bond_atom_site_label_2
 _geom_bond_distance
 _geom_bond_site_symmetry_2
 _geom_bond_publ_flag
S1 O3 1.4414(11) . ?
S1 O4 1.4414(11) . ?
S1 C2 1.7476(14) . ?
S1 C1 1.7605(14) . ?
O1 C7 1.3642(16) . ?
O1 C8 1.4287(17) . ?
O2 C6 1.3683(17) . ?
O2 C9 1.4258(17) . ?
C1 H1 0.9800 . ?
C1 H3 0.9800 . ?
C1 H16 0.9800 . ?
C2 C3 1.3423(19) . ?
C2 H15 0.9500 . ?
C3 C4 1.4775(18) . ?
C3 C13 1.4897(18) . ?
C4 C11 1.3895(19) . ?
C4 C5 1.3937(19) . ?
C5 C6 1.3829(19) . ?
C5 H4 0.9500 . ?
C6 C7 1.4156(19) . ?
C7 C10 1.384(2) . ?
C8 H9 0.9800 . ?
C8 H8 0.9800 . ?
C8 H2 0.9800 . ?
C9 H6 0.9800 . ?
C9 H7 0.9800 . ?
C9 H5 0.9800 . ?
C10 C11 1.3919(19) . ?
C10 H14 0.9500 . ?
C11 C12 1.4662(19) . ?
C12 C17 1.3817(19) . ?
C12 C13 1.4159(19) . ?
C13 C14 1.388(2) . ?
C14 C15 1.395(2) . ?
C14 H13 0.9500 . ?
C15 C16 1.387(2) . ?
C15 H12 0.9500 . ?
C16 C17 1.390(2) . ?
C16 H11 0.9500 . ?
C17 H10 0.9500 . ?
 
loop_
 _geom_angle_atom_site_label_1
 _geom_angle_atom_site_label_2
 _geom_angle_atom_site_label_3
 _geom_angle
 _geom_angle_site_symmetry_1
 _geom_angle_site_symmetry_3
 _geom_angle_publ_flag
O3 S1 O4 117.73(6) . . ?
O3 S1 C2 105.82(6) . . ?
O4 S1 C2 110.36(6) . . ?
O3 S1 C1 107.51(7) . . ?
O4 S1 C1 108.90(7) . . ?
C2 S1 C1 105.85(7) . . ?
C7 O1 C8 117.21(11) . . ?
C6 O2 C9 116.25(11) . . ?
S1 C1 H1 109.5 . . ?
S1 C1 H3 109.5 . . ?
H1 C1 H3 109.5 . . ?
S1 C1 H16 109.5 . . ?
H1 C1 H16 109.5 . . ?
H3 C1 H16 109.5 . . ?
C3 C2 S1 128.30(11) . . ?
C3 C2 H15 115.8 . . ?
S1 C2 H15 115.8 . . ?
C2 C3 C4 121.45(12) . . ?
C2 C3 C13 133.14(13) . . ?
C4 C3 C13 105.32(11) . . ?
C11 C4 C5 121.26(12) . . ?
C11 C4 C3 109.68(12) . . ?
C5 C4 C3 129.06(12) . . ?
C6 C5 C4 118.03(13) . . ?
C6 C5 H4 121.0 . . ?
C4 C5 H4 121.0 . . ?
O2 C6 C5 124.21(13) . . ?
O2 C6 C7 114.97(12) . . ?
C5 C6 C7 120.81(13) . . ?
O1 C7 C10 124.75(13) . . ?
O1 C7 C6 114.62(12) . . ?
C10 C7 C6 120.63(12) . . ?
O1 C8 H9 109.5 . . ?
O1 C8 H8 109.5 . . ?
H9 C8 H8 109.5 . . ?
O1 C8 H2 109.5 . . ?
H9 C8 H2 109.5 . . ?
H8 C8 H2 109.5 . . ?
O2 C9 H6 109.5 . . ?
O2 C9 H7 109.5 . . ?
H6 C9 H7 109.5 . . ?
O2 C9 H5 109.5 . . ?
H6 C9 H5 109.5 . . ?
H7 C9 H5 109.5 . . ?
C7 C10 C11 118.27(13) . . ?
C7 C10 H14 120.9 . . ?
C11 C10 H14 120.9 . . ?
C4 C11 C10 120.99(13) . . ?
C4 C11 C12 108.36(12) . . ?
C10 C11 C12 130.65(13) . . ?
C17 C12 C13 121.07(13) . . ?
C17 C12 C11 130.19(13) . . ?
C13 C12 C11 108.74(12) . . ?
C14 C13 C12 119.47(13) . . ?
C14 C13 C3 132.65(13) . . ?
C12 C13 C3 107.86(12) . . ?
C13 C14 C15 119.20(13) . . ?
C13 C14 H13 120.4 . . ?
C15 C14 H13 120.4 . . ?
C16 C15 C14 120.65(13) . . ?
C16 C15 H12 119.7 . . ?
C14 C15 H12 119.7 . . ?
C15 C16 C17 120.89(14) . . ?
C15 C16 H11 119.6 . . ?
C17 C16 H11 119.6 . . ?
C12 C17 C16 118.70(13) . . ?
C12 C17 H10 120.7 . . ?
C16 C17 H10 120.7 . . ?
 
_refine_diff_density_max    0.577
_refine_diff_density_min   -0.368
_refine_diff_density_rms    0.053

_shelxl_version_number 2014/6



 
data_mo_180861LT_0m
 
_audit_creation_method            SHELXL-2014/6
_chemical_name_systematic         ?
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C22 H17 F O4 S' 
_chemical_formula_weight          396.41

loop_
 _atom_type_symbol
 _atom_type_description
 _atom_type_scat_dispersion_real
 _atom_type_scat_dispersion_imag
 _atom_type_scat_source
 'C'  'C'   0.0033   0.0016
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'H'  'H'   0.0000   0.0000
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'O'  'O'   0.0106   0.0060
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'F'  'F'   0.0171   0.0103
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'S'  'S'   0.1246   0.1234
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 
_space_group_crystal_system       triclinic
_space_group_IT_number            2
_space_group_name_H-M_alt         'P -1'
_space_group_name_Hall            '-P 1'
 
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
 
loop_
 _space_group_symop_operation_xyz
 'x, y, z'
 '-x, -y, -z'
 
_cell_length_a                    9.0626(2)
_cell_length_b                    9.7391(2)
_cell_length_c                    11.0422(2)
_cell_angle_alpha                 74.2480(10)
_cell_angle_beta                  73.0790(10)
_cell_angle_gamma                 84.7060(10)
_cell_volume                      897.30(3)
_cell_formula_units_Z             2
_cell_measurement_temperature     99(2)
_cell_measurement_reflns_used     6993
_cell_measurement_theta_min       3.0412
_cell_measurement_theta_max       26.2387
 
_exptl_crystal_description        lump
_exptl_crystal_colour             red
_exptl_crystal_density_meas       'not measured'
_exptl_crystal_density_method     'not measured'
_exptl_crystal_density_diffrn     1.467          
_exptl_crystal_F_000              412
_exptl_transmission_factor_min    ?
_exptl_transmission_factor_max    ?
_exptl_crystal_size_max           0.17
_exptl_crystal_size_mid           0.15
_exptl_crystal_size_min           0.14
_exptl_absorpt_coefficient_mu     0.218
_shelx_estimated_absorpt_T_min    ?
_shelx_estimated_absorpt_T_max    ?
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.7175  
_exptl_absorpt_correction_T_max   0.7454
_exptl_absorpt_process_details    'SADABS V2014/4 (Bruker AXS Inc.)'
_exptl_absorpt_special_details    ?
_diffrn_ambient_temperature       99(2)
_diffrn_radiation_wavelength      0.71073
_diffrn_radiation_type            MoK\a
_diffrn_source                    ?
_diffrn_measurement_device_type   'Bruker APEX-II CCD'
_diffrn_measurement_method        'φ and ω scans'
_diffrn_detector_area_resol_mean  8.3333
_diffrn_reflns_number             20112
_diffrn_reflns_av_unetI/netI      0.0233
_diffrn_reflns_av_R_equivalents   0.0339
_diffrn_reflns_limit_h_min        -11
_diffrn_reflns_limit_h_max        11
_diffrn_reflns_limit_k_min        -12
_diffrn_reflns_limit_k_max        12
_diffrn_reflns_limit_l_min        -13
_diffrn_reflns_limit_l_max        13
_diffrn_reflns_theta_min          1.995
_diffrn_reflns_theta_max          26.441
_diffrn_reflns_theta_full         25.242
_diffrn_measured_fraction_theta_max   0.995
_diffrn_measured_fraction_theta_full  0.996
_diffrn_reflns_Laue_measured_fraction_max    0.995
_diffrn_reflns_Laue_measured_fraction_full   0.996
_diffrn_reflns_point_group_measured_fraction_max   0.995
_diffrn_reflns_point_group_measured_fraction_full  0.996
_reflns_number_total              3676
_reflns_number_gt                 3164
_reflns_threshold_expression      'I > 2σ(I)'
_reflns_Friedel_coverage          0.000
_reflns_Friedel_fraction_max      .
_reflns_Friedel_fraction_full     .
 
_reflns_special_details
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
 
_computing_data_collection        'Bruker APEX2'
_computing_cell_refinement        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction         'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution     ?
_computing_structure_refinement   'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics     'Bruker SHELXTL'
_computing_publication_material   'Bruker SHELXTL'
_refine_special_details           ?
_refine_ls_structure_factor_coef  Fsqd
_refine_ls_matrix_type            full
_refine_ls_weighting_scheme       calc
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0513P)²+0.5106P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary      ?
_atom_sites_solution_secondary    ?
_atom_sites_solution_hydrogens    geom
_refine_ls_hydrogen_treatment     constr
_refine_ls_extinction_method      none
_refine_ls_extinction_coef        .
_refine_ls_number_reflns          3676
_refine_ls_number_parameters      255
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0429
_refine_ls_R_factor_gt            0.0351
_refine_ls_wR_factor_ref          0.1040
_refine_ls_wR_factor_gt           0.0973
_refine_ls_goodness_of_fit_ref    1.090
_refine_ls_restrained_S_all       1.090
_refine_ls_shift/su_max           0.000
_refine_ls_shift/su_mean          0.000
 
loop_
 _atom_site_label
 _atom_site_type_symbol
 _atom_site_fract_x
 _atom_site_fract_y
 _atom_site_fract_z
 _atom_site_U_iso_or_equiv
 _atom_site_adp_type
 _atom_site_occupancy
 _atom_site_site_symmetry_order  
 _atom_site_calc_flag
 _atom_site_refinement_flags_posn
 _atom_site_refinement_flags_adp
 _atom_site_refinement_flags_occupancy
 _atom_site_disorder_assembly
 _atom_site_disorder_group
S1 S 0.53817(5) 0.47050(4) 0.23145(4) 0.01839(13) Uani 1 1 d . . . . .
F1 F 1.12065(13) 0.22529(13) 0.32461(12) 0.0332(3) Uani 1 1 d . . . . .
O1 O 0.80214(15) 1.26080(12) -0.26563(12) 0.0219(3) Uani 1 1 d . . . . .
O2 O 0.48495(16) 0.38070(13) 0.16882(13) 0.0273(3) Uani 1 1 d . . . . .
O3 O 0.44034(14) 0.49079(13) 0.35374(12) 0.0237(3) Uani 1 1 d . . . . .
O4 O 0.66334(15) 1.08175(13) -0.32145(12) 0.0214(3) Uani 1 1 d . . . . .
C1 C 0.9863(2) 0.28203(18) 0.30320(18) 0.0215(4) Uani 1 1 d . . . . .
C2 C 0.8625(2) 0.28572(18) 0.40941(18) 0.0224(4) Uani 1 1 d . . . . .
H14 H 0.8709 0.2486 0.4961 0.027 Uiso 1 1 calc R U . . .
C3 C 0.7247(2) 0.34535(18) 0.38649(17) 0.0204(4) Uani 1 1 d . . . . .
H15 H 0.6370 0.3499 0.4579 0.024 Uiso 1 1 calc R U . . .
C4 C 0.7160(2) 0.39797(17) 0.25921(16) 0.0176(3) Uani 1 1 d . . . . .
C5 C 0.58100(19) 0.63285(17) 0.11286(16) 0.0170(3) Uani 1 1 d . . . . .
H13 H 0.5558 0.6398 0.0337 0.020 Uiso 1 1 calc R U . . .
C6 C 0.64506(18) 0.74934(17) 0.11896(16) 0.0154(3) Uani 1 1 d . . . . .
C7 C 0.67897(18) 0.87722(17) 0.00704(16) 0.0152(3) Uani 1 1 d . . . . .
C8 C 0.64351(18) 0.90763(17) -0.11182(16) 0.0152(3) Uani 1 1 d . . . . .
H11 H 0.5901 0.8409 -0.1317 0.018 Uiso 1 1 calc R U . . .
C9 C 0.68802(19) 1.03784(17) -0.20063(16) 0.0168(3) Uani 1 1 d . . . . .
C10 C 0.76606(19) 1.13757(17) -0.16965(16) 0.0169(3) Uani 1 1 d . . . . .
C11 C 0.8689(2) 1.37098(18) -0.23753(19) 0.0254(4) Uani 1 1 d . . . . .
H1 H 0.7984 1.3978 -0.1613 0.038 Uiso 1 1 calc R U . . .
H6 H 0.8872 1.4542 -0.3133 0.038 Uiso 1 1 calc R U . . .
H7 H 0.9670 1.3368 -0.2186 0.038 Uiso 1 1 calc R U . . .
C12 C 0.9805(2) 0.33339(18) 0.17495(18) 0.0227(4) Uani 1 1 d . . . . .
H17 H 1.0687 0.3287 0.1041 0.027 Uiso 1 1 calc R U . . .
C13 C 0.8424(2) 0.39186(17) 0.15261(17) 0.0205(4) Uani 1 1 d . . . . .
H16 H 0.8341 0.4273 0.0657 0.025 Uiso 1 1 calc R U . . .
C14 C 0.75873(19) 0.97398(17) 0.03673(16) 0.0159(3) Uani 1 1 d . . . . .
C15 C 0.77823(19) 0.91270(17) 0.16759(16) 0.0164(3) Uani 1 1 d . . . . .
C16 C 0.70437(19) 0.77969(17) 0.22029(16) 0.0156(3) Uani 1 1 d . . . . .
C17 C 0.69617(19) 0.70517(18) 0.34885(16) 0.0179(3) Uani 1 1 d . . . . .
H2 H 0.6425 0.6176 0.3870 0.021 Uiso 1 1 calc R U . . .
C18 C 0.7676(2) 0.76049(18) 0.42089(17) 0.0201(4) Uani 1 1 d . . . . .
H5 H 0.7631 0.7100 0.5085 0.024 Uiso 1 1 calc R U . . .
C19 C 0.8453(2) 0.88907(19) 0.36575(17) 0.0209(4) Uani 1 1 d . . . . .
H4 H 0.8959 0.9240 0.4154 0.025 Uiso 1 1 calc R U . . .
C20 C 0.8500(2) 0.96678(18) 0.23961(17) 0.0195(4) Uani 1 1 d . . . . .
H3 H 0.9015 1.0555 0.2030 0.023 Uiso 1 1 calc R U . . .
C21 C 0.80154(19) 1.10615(17) -0.05130(17) 0.0174(3) Uani 1 1 d . . . . .
H12 H 0.8538 1.1730 -0.0305 0.021 Uiso 1 1 calc R U . . .
C22 C 0.5820(2) 0.98790(19) -0.35702(18) 0.0213(4) Uani 1 1 d . . . . .
H8 H 0.6375 0.8963 -0.3532 0.032 Uiso 1 1 calc R U . . .
H9 H 0.5740 1.0300 -0.4462 0.032 Uiso 1 1 calc R U . . .
H10 H 0.4783 0.9727 -0.2961 0.032 Uiso 1 1 calc R U . . .
 
 
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
 
loop_
 _geom_bond_atom_site_label_1
 _geom_bond_atom_site_label_2
 _geom_bond_distance
 _geom_bond_site_symmetry_2
 _geom_bond_publ_flag
S1 O3 1.4367(13) . ?
S1 O2 1.4408(13) . ?
S1 C5 1.7490(16) . ?
S1 C4 1.7751(18) . ?
F1 C1 1.348(2) . ?
O1 C10 1.3604(19) . ?
O1 C11 1.422(2) . ?
O4 C9 1.364(2) . ?
O4 C22 1.422(2) . ?
C1 C2 1.373(3) . ?
C1 C12 1.383(3) . ?
C2 C3 1.390(3) . ?
C2 H14 0.9500 . ?
C3 C4 1.382(2) . ?
C3 H15 0.9500 . ?
C4 C13 1.393(2) . ?
C5 C6 1.347(2) . ?
C5 H13 0.9500 . ?
C6 C7 1.479(2) . ?
C6 C16 1.479(2) . ?
C7 C8 1.389(2) . ?
C7 C14 1.396(2) . ?
C8 C9 1.386(2) . ?
C8 H11 0.9500 . ?
C9 C10 1.417(2) . ?
C10 C21 1.384(2) . ?
C11 H1 0.9800 . ?
C11 H6 0.9800 . ?
C11 H7 0.9800 . ?
C12 C13 1.386(3) . ?
C12 H17 0.9500 . ?
C13 H16 0.9500 . ?
C14 C21 1.395(2) . ?
C14 C15 1.462(2) . ?
C15 C20 1.388(2) . ?
C15 C16 1.410(2) . ?
C16 C17 1.392(2) . ?
C17 C18 1.392(2) . ?
C17 H2 0.9500 . ?
C18 C19 1.391(2) . ?
C18 H5 0.9500 . ?
C19 C20 1.383(2) . ?
C19 H4 0.9500 . ?
C20 H3 0.9500 . ?
C21 H12 0.9500 . ?
C22 H8 0.9800 . ?
C22 H9 0.9800 . ?
C22 H10 0.9800 . ?
 
loop_
 _geom_angle_atom_site_label_1
 _geom_angle_atom_site_label_2
 _geom_angle_atom_site_label_3
 _geom_angle
 _geom_angle_site_symmetry_1
 _geom_angle_site_symmetry_3
 _geom_angle_publ_flag
O3 S1 O2 118.42(8) . . ?
O3 S1 C5 111.54(8) . . ?
O2 S1 C5 104.86(8) . . ?
O3 S1 C4 107.24(8) . . ?
O2 S1 C4 107.71(8) . . ?
C5 S1 C4 106.46(8) . . ?
C10 O1 C11 117.43(13) . . ?
C9 O4 C22 117.17(13) . . ?
F1 C1 C2 118.47(16) . . ?
F1 C1 C12 118.08(16) . . ?
C2 C1 C12 123.45(17) . . ?
C1 C2 C3 118.12(16) . . ?
C1 C2 H14 120.9 . . ?
C3 C2 H14 120.9 . . ?
C4 C3 C2 119.58(16) . . ?
C4 C3 H15 120.2 . . ?
C2 C3 H15 120.2 . . ?
C3 C4 C13 121.48(17) . . ?
C3 C4 S1 119.08(13) . . ?
C13 C4 S1 119.41(13) . . ?
C6 C5 S1 128.55(14) . . ?
C6 C5 H13 115.7 . . ?
S1 C5 H13 115.7 . . ?
C5 C6 C7 121.69(15) . . ?
C5 C6 C16 132.44(16) . . ?
C7 C6 C16 105.74(14) . . ?
C8 C7 C14 121.30(15) . . ?
C8 C7 C6 129.92(15) . . ?
C14 C7 C6 108.77(14) . . ?
C9 C8 C7 118.31(15) . . ?
C9 C8 H11 120.8 . . ?
C7 C8 H11 120.8 . . ?
O4 C9 C8 125.00(15) . . ?
O4 C9 C10 114.47(14) . . ?
C8 C9 C10 120.53(15) . . ?
O1 C10 C21 125.08(15) . . ?
O1 C10 C9 114.14(15) . . ?
C21 C10 C9 120.78(15) . . ?
O1 C11 H1 109.5 . . ?
O1 C11 H6 109.5 . . ?
H1 C11 H6 109.5 . . ?
O1 C11 H7 109.5 . . ?
H1 C11 H7 109.5 . . ?
H6 C11 H7 109.5 . . ?
C1 C12 C13 118.22(16) . . ?
C1 C12 H17 120.9 . . ?
C13 C12 H17 120.9 . . ?
C12 C13 C4 119.15(16) . . ?
C12 C13 H16 120.4 . . ?
C4 C13 H16 120.4 . . ?
C21 C14 C7 120.65(15) . . ?
C21 C14 C15 130.68(15) . . ?
C7 C14 C15 108.63(14) . . ?
C20 C15 C16 120.96(16) . . ?
C20 C15 C14 130.42(15) . . ?
C16 C15 C14 108.60(14) . . ?
C17 C16 C15 119.51(16) . . ?
C17 C16 C6 132.38(15) . . ?
C15 C16 C6 108.09(14) . . ?
C16 C17 C18 119.16(16) . . ?
C16 C17 H2 120.4 . . ?
C18 C17 H2 120.4 . . ?
C19 C18 C17 120.61(16) . . ?
C19 C18 H5 119.7 . . ?
C17 C18 H5 119.7 . . ?
C20 C19 C18 120.91(16) . . ?
C20 C19 H4 119.5 . . ?
C18 C19 H4 119.5 . . ?
C19 C20 C15 118.75(16) . . ?
C19 C20 H3 120.6 . . ?
C15 C20 H3 120.6 . . ?
C10 C21 C14 118.41(15) . . ?
C10 C21 H12 120.8 . . ?
C14 C21 H12 120.8 . . ?
O4 C22 H8 109.5 . . ?
O4 C22 H9 109.5 . . ?
H8 C22 H9 109.5 . . ?
O4 C22 H10 109.5 . . ?
H8 C22 H10 109.5 . . ?
H9 C22 H10 109.5 . . ?
 
_refine_diff_density_max    0.362
_refine_diff_density_min   -0.354
_refine_diff_density_rms    0.059

_shelxl_version_number 2014/6



 
data_180907LT_0m
 
_audit_creation_method            SHELXL-2014/6
_chemical_name_systematic         ?
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C24 H22 O5 S' 
_chemical_formula_weight          422.47

loop_
 _atom_type_symbol
 _atom_type_description
 _atom_type_scat_dispersion_real
 _atom_type_scat_dispersion_imag
 _atom_type_scat_source
 'C'  'C'   0.0033   0.0016
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'H'  'H'   0.0000   0.0000
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'O'  'O'   0.0106   0.0060
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'S'  'S'   0.1246   0.1234
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 
_space_group_crystal_system       triclinic
_space_group_IT_number            2
_space_group_name_H-M_alt         'P -1'
_space_group_name_Hall            '-P 1'
 
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
 
loop_
 _space_group_symop_operation_xyz
 'x, y, z'
 '-x, -y, -z'
 
_cell_length_a                    9.4622(6)
_cell_length_b                    9.7507(6)
_cell_length_c                    13.1691(10)
_cell_angle_alpha                 98.226(3)
_cell_angle_beta                  101.267(3)
_cell_angle_gamma                 117.085(3)
_cell_volume                      1022.78(12)
_cell_formula_units_Z             2
_cell_measurement_temperature     100(2)
_cell_measurement_reflns_used     9994
_cell_measurement_theta_min       2.4889
_cell_measurement_theta_max       26.4091
 
_exptl_crystal_description        lump
_exptl_crystal_colour             colorless
_exptl_crystal_density_meas       'not measured'
_exptl_crystal_density_method     'not measured'
_exptl_crystal_density_diffrn     1.372          
_exptl_crystal_F_000              444
_exptl_transmission_factor_min    ?
_exptl_transmission_factor_max    ?
_exptl_crystal_size_max           0.13
_exptl_crystal_size_mid           0.10
_exptl_crystal_size_min           0.10
_exptl_absorpt_coefficient_mu     0.192
_shelx_estimated_absorpt_T_min    ?
_shelx_estimated_absorpt_T_max    ?
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.5514  
_exptl_absorpt_correction_T_max   0.7454
_exptl_absorpt_process_details    'SADABS V2014/4 (Bruker AXS Inc.)'
_exptl_absorpt_special_details    ?
_diffrn_ambient_temperature       100(2)
_diffrn_radiation_wavelength      0.71073
_diffrn_radiation_type            MoK\a
_diffrn_source                    ?
_diffrn_measurement_device_type   'Bruker APEX-II CCD'
_diffrn_measurement_method        'φ and ω scans'
_diffrn_detector_area_resol_mean  8.3333
_diffrn_reflns_number             30196
_diffrn_reflns_av_unetI/netI      0.0392
_diffrn_reflns_av_R_equivalents   0.0551
_diffrn_reflns_limit_h_min        -11
_diffrn_reflns_limit_h_max        9
_diffrn_reflns_limit_k_min        -12
_diffrn_reflns_limit_k_max        12
_diffrn_reflns_limit_l_min        -16
_diffrn_reflns_limit_l_max        16
_diffrn_reflns_theta_min          1.636
_diffrn_reflns_theta_max          26.507
_diffrn_reflns_theta_full         25.242
_diffrn_measured_fraction_theta_max   0.971
_diffrn_measured_fraction_theta_full  0.981
_diffrn_reflns_Laue_measured_fraction_max    0.971
_diffrn_reflns_Laue_measured_fraction_full   0.981
_diffrn_reflns_point_group_measured_fraction_max   0.971
_diffrn_reflns_point_group_measured_fraction_full  0.981
_reflns_number_total              4125
_reflns_number_gt                 3398
_reflns_threshold_expression      'I > 2σ(I)'
_reflns_Friedel_coverage          0.000
_reflns_Friedel_fraction_max      .
_reflns_Friedel_fraction_full     .
 
_reflns_special_details
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
 
_computing_data_collection        'Bruker APEX2'
_computing_cell_refinement        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction         'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution     ?
_computing_structure_refinement   'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics     'Bruker SHELXTL'
_computing_publication_material   'Bruker SHELXTL'
_refine_special_details           ?
_refine_ls_structure_factor_coef  Fsqd
_refine_ls_matrix_type            full
_refine_ls_weighting_scheme       calc
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0638P)²+1.3017P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary      ?
_atom_sites_solution_secondary    ?
_atom_sites_solution_hydrogens    geom
_refine_ls_hydrogen_treatment     constr
_refine_ls_extinction_method      none
_refine_ls_extinction_coef        .
_refine_ls_number_reflns          4125
_refine_ls_number_parameters      275
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0724
_refine_ls_R_factor_gt            0.0617
_refine_ls_wR_factor_ref          0.1696
_refine_ls_wR_factor_gt           0.1574
_refine_ls_goodness_of_fit_ref    1.163
_refine_ls_restrained_S_all       1.163
_refine_ls_shift/su_max           0.000
_refine_ls_shift/su_mean          0.000
 
loop_
 _atom_site_label
 _atom_site_type_symbol
 _atom_site_fract_x
 _atom_site_fract_y
 _atom_site_fract_z
 _atom_site_U_iso_or_equiv
 _atom_site_adp_type
 _atom_site_occupancy
 _atom_site_site_symmetry_order  
 _atom_site_calc_flag
 _atom_site_refinement_flags_posn
 _atom_site_refinement_flags_adp
 _atom_site_refinement_flags_occupancy
 _atom_site_disorder_assembly
 _atom_site_disorder_group
S1 S 0.41649(8) 0.34714(8) 0.16546(5) 0.0280(2) Uani 1 1 d . . . . .
O1 O 0.8473(2) 1.3184(2) 0.43009(16) 0.0316(5) Uani 1 1 d . . . . .
O2 O 0.3691(3) 0.2609(2) 0.24394(17) 0.0368(5) Uani 1 1 d . . . . .
O3 O 0.2863(2) 0.3243(3) 0.07601(17) 0.0373(5) Uani 1 1 d . . . . .
O4 O 0.8644(2) 0.8561(2) 0.28548(15) 0.0299(5) Uani 1 1 d . . . . .
O5 O 1.0133(2) 1.1861(2) 0.36345(16) 0.0331(5) Uani 1 1 d . . . . .
C1 C 0.7590(4) 1.3982(3) 0.4546(2) 0.0325(6) Uani 1 1 d . . . . .
H14 H 0.6729 1.3766 0.3896 0.049 Uiso 1 1 calc R U . . .
H1 H 0.8364 1.5135 0.4813 0.049 Uiso 1 1 calc R U . . .
H13 H 0.7071 1.3593 0.5097 0.049 Uiso 1 1 calc R U . . .
C2 C 0.7601(3) 1.1575(3) 0.3915(2) 0.0251(6) Uani 1 1 d . . . . .
C3 C 0.8513(3) 1.0880(3) 0.3593(2) 0.0269(6) Uani 1 1 d . . . . .
C4 C 0.7744(3) 0.9238(3) 0.3167(2) 0.0248(6) Uani 1 1 d . . . . .
C5 C 0.6085(3) 0.8282(3) 0.3088(2) 0.0249(6) Uani 1 1 d . . . . .
C6 C 0.4958(3) 0.6537(3) 0.2655(2) 0.0254(6) Uani 1 1 d . . . . .
C7 C 0.5435(3) 0.5521(3) 0.2271(2) 0.0294(6) Uani 1 1 d . . . . .
H6 H 0.6585 0.5959 0.2341 0.035 Uiso 1 1 calc R U . . .
C8 C 0.5507(3) 0.2996(3) 0.1145(2) 0.0281(6) Uani 1 1 d . . . . .
C9 C 0.5731(3) 0.1763(3) 0.1405(2) 0.0293(6) Uani 1 1 d . . . . .
H5 H 0.5214 0.1229 0.1889 0.035 Uiso 1 1 calc R U . . .
C10 C 0.6711(4) 0.1320(4) 0.0954(2) 0.0336(7) Uani 1 1 d . . . . .
H4 H 0.6855 0.0472 0.1131 0.040 Uiso 1 1 calc R U . . .
C11 C 0.7483(4) 0.2078(4) 0.0254(2) 0.0367(7) Uani 1 1 d . . . . .
C12 C 0.8547(4) 0.1597(5) -0.0234(3) 0.0527(10) Uani 1 1 d . . . . .
H3 H 0.9718 0.2420 0.0092 0.079 Uiso 1 1 calc R U . . .
H22 H 0.8237 0.1480 -0.1009 0.079 Uiso 1 1 calc R U . . .
H2 H 0.8384 0.0578 -0.0104 0.079 Uiso 1 1 calc R U . . .
C13 C 0.3313(3) 0.6272(3) 0.2741(2) 0.0250(6) Uani 1 1 d . . . . .
C14 C 0.3469(3) 0.7753(3) 0.3164(2) 0.0245(6) Uani 1 1 d . . . . .
C15 C 0.5197(3) 0.9006(3) 0.3393(2) 0.0237(6) Uani 1 1 d . . . . .
C16 C 0.9023(5) 0.8838(5) 0.1875(3) 0.0510(9) Uani 1 1 d . . . . .
H9 H 0.7994 0.8474 0.1306 0.076 Uiso 1 1 calc R U . . .
H8 H 0.9571 0.8245 0.1667 0.076 Uiso 1 1 calc R U . . .
H7 H 0.9764 0.9982 0.1982 0.076 Uiso 1 1 calc R U . . .
C17 C 1.1346(4) 1.1818(4) 0.4439(3) 0.0399(7) Uani 1 1 d . . . . .
H12 H 1.1262 1.2168 0.5149 0.060 Uiso 1 1 calc R U . . .
H11 H 1.2457 1.2530 0.4396 0.060 Uiso 1 1 calc R U . . .
H10 H 1.1155 1.0724 0.4325 0.060 Uiso 1 1 calc R U . . .
C18 C 0.5930(3) 1.0639(3) 0.3811(2) 0.0254(6) Uani 1 1 d . . . . .
H15 H 0.5306 1.1103 0.4021 0.030 Uiso 1 1 calc R U . . .
C19 C 0.2119(3) 0.7873(3) 0.3314(2) 0.0281(6) Uani 1 1 d . . . . .
H19 H 0.2225 0.8883 0.3584 0.034 Uiso 1 1 calc R U . . .
C20 C 0.0605(3) 0.6475(4) 0.3058(2) 0.0334(7) Uani 1 1 d . . . . .
H18 H -0.0339 0.6528 0.3155 0.040 Uiso 1 1 calc R U . . .
C21 C 0.0453(3) 0.5013(3) 0.2666(2) 0.0307(6) Uani 1 1 d . . . . .
H17 H -0.0593 0.4071 0.2506 0.037 Uiso 1 1 calc R U . . .
C22 C 0.1793(3) 0.4891(3) 0.2502(2) 0.0292(6) Uani 1 1 d . . . . .
H16 H 0.1674 0.3875 0.2229 0.035 Uiso 1 1 calc R U . . .
C23 C 0.6273(4) 0.3773(4) 0.0443(2) 0.0363(7) Uani 1 1 d . . . . .
H20 H 0.6119 0.4614 0.0261 0.044 Uiso 1 1 calc R U . . .
C24 C 0.7254(4) 0.3325(4) 0.0011(2) 0.0396(7) Uani 1 1 d . . . . .
H21 H 0.7789 0.3873 -0.0462 0.048 Uiso 1 1 calc R U . . .
 
 
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
 
loop_
 _geom_bond_atom_site_label_1
 _geom_bond_atom_site_label_2
 _geom_bond_distance
 _geom_bond_site_symmetry_2
 _geom_bond_publ_flag
S1 O2 1.436(2) . ?
S1 O3 1.437(2) . ?
S1 C8 1.748(3) . ?
S1 C7 1.750(3) . ?
O1 C2 1.353(3) . ?
O1 C1 1.425(3) . ?
O4 C4 1.379(3) . ?
O4 C16 1.435(4) . ?
O5 C3 1.373(3) . ?
O5 C17 1.422(4) . ?
C1 H14 0.9800 . ?
C1 H1 0.9800 . ?
C1 H13 0.9800 . ?
C2 C18 1.385(4) . ?
C2 C3 1.405(4) . ?
C3 C4 1.390(4) . ?
C4 C5 1.386(4) . ?
C5 C15 1.399(4) . ?
C5 C6 1.479(4) . ?
C6 C7 1.340(4) . ?
C6 C13 1.487(4) . ?
C7 H6 0.9500 . ?
C8 C23 1.384(4) . ?
C8 C9 1.389(4) . ?
C9 C10 1.380(4) . ?
C9 H5 0.9500 . ?
C10 C11 1.377(4) . ?
C10 H4 0.9500 . ?
C11 C24 1.396(5) . ?
C11 C12 1.498(4) . ?
C12 H3 0.9800 . ?
C12 H22 0.9800 . ?
C12 H2 0.9800 . ?
C13 C22 1.386(4) . ?
C13 C14 1.401(4) . ?
C14 C19 1.383(4) . ?
C14 C15 1.463(4) . ?
C15 C18 1.383(4) . ?
C16 H9 0.9800 . ?
C16 H8 0.9800 . ?
C16 H7 0.9800 . ?
C17 H12 0.9800 . ?
C17 H11 0.9800 . ?
C17 H10 0.9800 . ?
C18 H15 0.9500 . ?
C19 C20 1.388(4) . ?
C19 H19 0.9500 . ?
C20 C21 1.375(4) . ?
C20 H18 0.9500 . ?
C21 C22 1.380(4) . ?
C21 H17 0.9500 . ?
C22 H16 0.9500 . ?
C23 C24 1.372(4) . ?
C23 H20 0.9500 . ?
C24 H21 0.9500 . ?
 
loop_
 _geom_angle_atom_site_label_1
 _geom_angle_atom_site_label_2
 _geom_angle_atom_site_label_3
 _geom_angle
 _geom_angle_site_symmetry_1
 _geom_angle_site_symmetry_3
 _geom_angle_publ_flag
O2 S1 O3 117.69(13) . . ?
O2 S1 C8 108.76(13) . . ?
O3 S1 C8 107.90(13) . . ?
O2 S1 C7 110.53(13) . . ?
O3 S1 C7 108.64(13) . . ?
C8 S1 C7 102.16(13) . . ?
C2 O1 C1 117.9(2) . . ?
C4 O4 C16 113.8(2) . . ?
C3 O5 C17 115.2(2) . . ?
O1 C1 H14 109.5 . . ?
O1 C1 H1 109.5 . . ?
H14 C1 H1 109.5 . . ?
O1 C1 H13 109.5 . . ?
H14 C1 H13 109.5 . . ?
H1 C1 H13 109.5 . . ?
O1 C2 C18 124.4(2) . . ?
O1 C2 C3 114.9(2) . . ?
C18 C2 C3 120.7(2) . . ?
O5 C3 C4 120.8(2) . . ?
O5 C3 C2 118.8(2) . . ?
C4 C3 C2 120.2(2) . . ?
O4 C4 C5 120.2(2) . . ?
O4 C4 C3 120.0(2) . . ?
C5 C4 C3 119.7(2) . . ?
C4 C5 C15 118.9(2) . . ?
C4 C5 C6 131.3(2) . . ?
C15 C5 C6 109.6(2) . . ?
C7 C6 C5 123.8(2) . . ?
C7 C6 C13 131.4(3) . . ?
C5 C6 C13 104.8(2) . . ?
C6 C7 S1 127.0(2) . . ?
C6 C7 H6 116.5 . . ?
S1 C7 H6 116.5 . . ?
C23 C8 C9 119.8(3) . . ?
C23 C8 S1 120.8(2) . . ?
C9 C8 S1 119.3(2) . . ?
C10 C9 C8 119.5(3) . . ?
C10 C9 H5 120.2 . . ?
C8 C9 H5 120.2 . . ?
C11 C10 C9 121.5(3) . . ?
C11 C10 H4 119.2 . . ?
C9 C10 H4 119.2 . . ?
C10 C11 C24 118.0(3) . . ?
C10 C11 C12 121.5(3) . . ?
C24 C11 C12 120.4(3) . . ?
C11 C12 H3 109.5 . . ?
C11 C12 H22 109.5 . . ?
H3 C12 H22 109.5 . . ?
C11 C12 H2 109.5 . . ?
H3 C12 H2 109.5 . . ?
H22 C12 H2 109.5 . . ?
C22 C13 C14 119.6(3) . . ?
C22 C13 C6 131.8(3) . . ?
C14 C13 C6 108.6(2) . . ?
C19 C14 C13 121.3(2) . . ?
C19 C14 C15 129.6(3) . . ?
C13 C14 C15 109.1(2) . . ?
C18 C15 C5 122.4(2) . . ?
C18 C15 C14 129.7(2) . . ?
C5 C15 C14 107.9(2) . . ?
O4 C16 H9 109.5 . . ?
O4 C16 H8 109.5 . . ?
H9 C16 H8 109.5 . . ?
O4 C16 H7 109.5 . . ?
H9 C16 H7 109.5 . . ?
H8 C16 H7 109.5 . . ?
O5 C17 H12 109.5 . . ?
O5 C17 H11 109.5 . . ?
H12 C17 H11 109.5 . . ?
O5 C17 H10 109.5 . . ?
H12 C17 H10 109.5 . . ?
H11 C17 H10 109.5 . . ?
C15 C18 C2 118.0(2) . . ?
C15 C18 H15 121.0 . . ?
C2 C18 H15 121.0 . . ?
C14 C19 C20 118.0(3) . . ?
C14 C19 H19 121.0 . . ?
C20 C19 H19 121.0 . . ?
C21 C20 C19 120.9(3) . . ?
C21 C20 H18 119.5 . . ?
C19 C20 H18 119.5 . . ?
C20 C21 C22 121.2(3) . . ?
C20 C21 H17 119.4 . . ?
C22 C21 H17 119.4 . . ?
C21 C22 C13 118.9(3) . . ?
C21 C22 H16 120.5 . . ?
C13 C22 H16 120.5 . . ?
C24 C23 C8 119.8(3) . . ?
C24 C23 H20 120.1 . . ?
C8 C23 H20 120.1 . . ?
C23 C24 C11 121.3(3) . . ?
C23 C24 H21 119.4 . . ?
C11 C24 H21 119.4 . . ?
 
_refine_diff_density_max    0.368
_refine_diff_density_min   -0.682
_refine_diff_density_rms    0.077

_shelxl_version_number 2014/6



 
data_180905lt_0m_a_sq
 
_audit_creation_method            SHELXL-2014/6
_chemical_name_systematic         ?
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C24 H22 O6 S' 
_chemical_formula_weight          438.47

loop_
 _atom_type_symbol
 _atom_type_description
 _atom_type_scat_dispersion_real
 _atom_type_scat_dispersion_imag
 _atom_type_scat_source
 'C'  'C'   0.0033   0.0016
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'H'  'H'   0.0000   0.0000
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'O'  'O'   0.0106   0.0060
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'S'  'S'   0.1246   0.1234
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 
_space_group_crystal_system       triclinic
_space_group_IT_number            2
_space_group_name_H-M_alt         'P -1'
_space_group_name_Hall            '-P 1'
 
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
 
loop_
 _space_group_symop_operation_xyz
 'x, y, z'
 '-x, -y, -z'
 
_cell_length_a                    12.1394(8)
_cell_length_b                    12.8311(9)
_cell_length_c                    16.4085(12)
_cell_angle_alpha                 107.146(3)
_cell_angle_beta                  97.160(3)
_cell_angle_gamma                 95.193(3)
_cell_volume                      2401.3(3)
_cell_formula_units_Z             4
_cell_measurement_temperature     100(2)
_cell_measurement_reflns_used     9033
_cell_measurement_theta_min       2.4305
_cell_measurement_theta_max       26.4105
 
_exptl_crystal_description        columnar
_exptl_crystal_colour             colorless
_exptl_crystal_density_meas       'not measured'
_exptl_crystal_density_method     'not measured'
_exptl_crystal_density_diffrn     1.213          
_exptl_crystal_F_000              920
_exptl_transmission_factor_min    ?
_exptl_transmission_factor_max    ?
_exptl_crystal_size_max           0.16
_exptl_crystal_size_mid           0.05
_exptl_crystal_size_min           0.04
_exptl_absorpt_coefficient_mu     0.169
_shelx_estimated_absorpt_T_min    ?
_shelx_estimated_absorpt_T_max    ?
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.6725  
_exptl_absorpt_correction_T_max   0.7454
_exptl_absorpt_process_details    'SADABS V2014/4 (Bruker AXS Inc.)'
_exptl_absorpt_special_details    ?
_diffrn_ambient_temperature       100(2)
_diffrn_radiation_wavelength      0.71073
_diffrn_radiation_type            MoK\a
_diffrn_source                    ?
_diffrn_measurement_device_type   'Bruker APEX-II CCD'
_diffrn_measurement_method        'φ and ω scans'
_diffrn_detector_area_resol_mean  8.3333
_diffrn_reflns_number             30022
_diffrn_reflns_av_unetI/netI      0.0803
_diffrn_reflns_av_R_equivalents   0.0560
_diffrn_reflns_limit_h_min        -15
_diffrn_reflns_limit_h_max        15
_diffrn_reflns_limit_k_min        -16
_diffrn_reflns_limit_k_max        16
_diffrn_reflns_limit_l_min        -20
_diffrn_reflns_limit_l_max        20
_diffrn_reflns_theta_min          1.315
_diffrn_reflns_theta_max          26.466
_diffrn_reflns_theta_full         25.242
_diffrn_measured_fraction_theta_max   0.932
_diffrn_measured_fraction_theta_full  0.948
_diffrn_reflns_Laue_measured_fraction_max    0.932
_diffrn_reflns_Laue_measured_fraction_full   0.948
_diffrn_reflns_point_group_measured_fraction_max   0.932
_diffrn_reflns_point_group_measured_fraction_full  0.948
_reflns_number_total              9234
_reflns_number_gt                 6170
_reflns_threshold_expression      'I > 2σ(I)'
_reflns_Friedel_coverage          0.000
_reflns_Friedel_fraction_max      .
_reflns_Friedel_fraction_full     .
 
_reflns_special_details
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
 
_computing_data_collection        'Bruker APEX2'
_computing_cell_refinement        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction         'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution     ?
_computing_structure_refinement   'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics     'Bruker SHELXTL'
_computing_publication_material   'Bruker SHELXTL'
_refine_special_details           ?
_refine_ls_structure_factor_coef  Fsqd
_refine_ls_matrix_type            full
_refine_ls_weighting_scheme       calc
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0630P)²+4.1609P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary      ?
_atom_sites_solution_secondary    ?
_atom_sites_solution_hydrogens    geom
_refine_ls_hydrogen_treatment     constr
_refine_ls_extinction_method      SHELXL
_refine_ls_extinction_coef        0.0014(5)
_refine_ls_extinction_expression
 'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
_refine_ls_number_reflns          9234
_refine_ls_number_parameters      568
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.1030
_refine_ls_R_factor_gt            0.0669
_refine_ls_wR_factor_ref          0.1813
_refine_ls_wR_factor_gt           0.1621
_refine_ls_goodness_of_fit_ref    1.079
_refine_ls_restrained_S_all       1.079
_refine_ls_shift/su_max           0.000
_refine_ls_shift/su_mean          0.000
 
loop_
 _atom_site_label
 _atom_site_type_symbol
 _atom_site_fract_x
 _atom_site_fract_y
 _atom_site_fract_z
 _atom_site_U_iso_or_equiv
 _atom_site_adp_type
 _atom_site_occupancy
 _atom_site_site_symmetry_order  
 _atom_site_calc_flag
 _atom_site_refinement_flags_posn
 _atom_site_refinement_flags_adp
 _atom_site_refinement_flags_occupancy
 _atom_site_disorder_assembly
 _atom_site_disorder_group
C1 C 0.8938(3) 0.9001(3) 0.3276(2) 0.0218(8) Uani 1 1 d . . . . .
C2 C 0.9980(3) 0.8990(4) 0.3713(3) 0.0322(10) Uani 1 1 d . . . . .
H2 H 1.0220 0.9487 0.4279 0.039 Uiso 1 1 calc R U . . .
C3 C 1.0676(3) 0.8267(4) 0.3338(3) 0.0334(10) Uani 1 1 d . . . . .
H3 H 1.1388 0.8254 0.3647 0.040 Uiso 1 1 calc R U . . .
C4 C 1.0335(3) 0.7559(3) 0.2507(2) 0.0269(9) Uani 1 1 d . . . . .
C5 C 0.9287(3) 0.7565(3) 0.2060(2) 0.0292(9) Uani 1 1 d . . . . .
H5 H 0.9055 0.7081 0.1489 0.035 Uiso 1 1 calc R U . . .
C6 C 0.8586(3) 0.8273(3) 0.2448(2) 0.0265(9) Uani 1 1 d . . . . .
H6 H 0.7860 0.8266 0.2151 0.032 Uiso 1 1 calc R U . . .
C7 C 1.2049(4) 0.6773(5) 0.2528(3) 0.0540(15) Uani 1 1 d . . . . .
H7A H 1.2496 0.7502 0.2729 0.081 Uiso 1 1 calc R U . . .
H7B H 1.2441 0.6253 0.2140 0.081 Uiso 1 1 calc R U . . .
H7C H 1.1940 0.6522 0.3025 0.081 Uiso 1 1 calc R U . . .
C8 C 0.7594(3) 0.9330(3) 0.4516(2) 0.0226(8) Uani 1 1 d . . . . .
H8 H 0.7795 0.8623 0.4486 0.027 Uiso 1 1 calc R U . . .
C9 C 0.6980(3) 0.9764(3) 0.5129(2) 0.0185(8) Uani 1 1 d . . . . .
C10 C 0.6592(3) 0.9184(3) 0.5721(2) 0.0193(8) Uani 1 1 d . . . . .
C11 C 0.6797(3) 0.8169(3) 0.5816(2) 0.0185(8) Uani 1 1 d . . . . .
C12 C 0.6299(3) 0.7806(3) 0.6424(2) 0.0220(8) Uani 1 1 d . . . . .
C13 C 0.5605(3) 0.8441(3) 0.6929(2) 0.0232(8) Uani 1 1 d . . . . .
C14 C 0.5401(3) 0.9453(3) 0.6835(2) 0.0219(8) Uani 1 1 d . . . . .
H14 H 0.4929 0.9889 0.7173 0.026 Uiso 1 1 calc R U . . .
C15 C 0.5910(3) 0.9810(3) 0.6232(2) 0.0204(8) Uani 1 1 d . . . . .
C16 C 0.5832(3) 1.0827(3) 0.6006(2) 0.0209(8) Uani 1 1 d . . . . .
C17 C 0.5235(3) 1.1692(3) 0.6317(2) 0.0224(8) Uani 1 1 d . . . . .
H17 H 0.4786 1.1688 0.6751 0.027 Uiso 1 1 calc R U . . .
C18 C 0.5308(3) 1.2566(3) 0.5979(2) 0.0270(9) Uani 1 1 d . . . . .
H18 H 0.4906 1.3167 0.6186 0.032 Uiso 1 1 calc R U . . .
C19 C 0.5964(3) 1.2568(3) 0.5343(2) 0.0273(9) Uani 1 1 d . . . . .
H19 H 0.6012 1.3176 0.5125 0.033 Uiso 1 1 calc R U . . .
C20 C 0.6550(3) 1.1692(3) 0.5019(2) 0.0230(8) Uani 1 1 d . . . . .
H20 H 0.6988 1.1695 0.4579 0.028 Uiso 1 1 calc R U . . .
C21 C 0.6485(3) 1.0819(3) 0.5349(2) 0.0205(8) Uani 1 1 d . . . . .
C22 C 0.8552(4) 0.7537(4) 0.5717(3) 0.0434(12) Uani 1 1 d . . . . .
H22A H 0.8940 0.8292 0.5908 0.065 Uiso 1 1 calc R U . . .
H22B H 0.8956 0.7060 0.5308 0.065 Uiso 1 1 calc R U . . .
H22C H 0.8524 0.7273 0.6218 0.065 Uiso 1 1 calc R U . . .
C23 C 0.5788(4) 0.5893(3) 0.5990(3) 0.0375(11) Uani 1 1 d . . . . .
H23A H 0.5017 0.5978 0.6087 0.056 Uiso 1 1 calc R U . . .
H23B H 0.5994 0.5225 0.6108 0.056 Uiso 1 1 calc R U . . .
H23C H 0.5847 0.5835 0.5388 0.056 Uiso 1 1 calc R U . . .
C24 C 0.4515(5) 0.8690(4) 0.8062(3) 0.0508(14) Uani 1 1 d . . . . .
H24A H 0.4971 0.9396 0.8383 0.076 Uiso 1 1 calc R U . . .
H24B H 0.4278 0.8322 0.8469 0.076 Uiso 1 1 calc R U . . .
H24C H 0.3853 0.8817 0.7716 0.076 Uiso 1 1 calc R U . . .
C25 C 0.8070(3) 0.1517(3) 0.9317(2) 0.0204(8) Uani 1 1 d . . . . .
C26 C 0.9143(3) 0.1388(3) 0.9653(2) 0.0227(8) Uani 1 1 d . . . . .
H26 H 0.9456 0.1794 1.0233 0.027 Uiso 1 1 calc R U . . .
C27 C 0.9755(3) 0.0672(3) 0.9149(2) 0.0216(8) Uani 1 1 d . . . . .
H27 H 1.0484 0.0581 0.9382 0.026 Uiso 1 1 calc R U . . .
C28 C 0.9301(3) 0.0087(3) 0.8303(2) 0.0240(9) Uani 1 1 d . . . . .
C29 C 0.8235(3) 0.0231(3) 0.7963(3) 0.0288(9) Uani 1 1 d . . . . .
H29 H 0.7929 -0.0165 0.7380 0.035 Uiso 1 1 calc R U . . .
C30 C 0.7623(3) 0.0937(3) 0.8464(3) 0.0287(9) Uani 1 1 d . . . . .
H30 H 0.6897 0.1030 0.8228 0.034 Uiso 1 1 calc R U . . .
C31 C 1.0902(4) -0.0853(4) 0.8058(3) 0.0362(11) Uani 1 1 d . . . . .
H31A H 1.1416 -0.0162 0.8258 0.054 Uiso 1 1 calc R U . . .
H31B H 1.1179 -0.1382 0.7591 0.054 Uiso 1 1 calc R U . . .
H31C H 1.0858 -0.1154 0.8539 0.054 Uiso 1 1 calc R U . . .
C32 C 0.7485(3) 0.3640(3) 0.9852(2) 0.0217(8) Uani 1 1 d . . . . .
H32 H 0.7995 0.3731 0.9476 0.026 Uiso 1 1 calc R U . . .
C33 C 0.7013(3) 0.4521(3) 1.0235(2) 0.0173(8) Uani 1 1 d . . . . .
C34 C 0.7218(3) 0.5605(3) 1.0100(2) 0.0193(8) Uani 1 1 d . . . . .
C35 C 0.7939(3) 0.6002(3) 0.9623(2) 0.0187(8) Uani 1 1 d . . . . .
C36 C 0.7922(3) 0.7067(3) 0.9583(2) 0.0192(8) Uani 1 1 d . . . . .
C37 C 0.7217(3) 0.7754(3) 1.0035(2) 0.0206(8) Uani 1 1 d . . . . .
C38 C 0.6502(3) 0.7378(3) 1.0523(2) 0.0203(8) Uani 1 1 d . . . . .
H38 H 0.6020 0.7839 1.0827 0.024 Uiso 1 1 calc R U . . .
C39 C 0.6521(3) 0.6311(3) 1.0548(2) 0.0194(8) Uani 1 1 d . . . . .
C40 C 0.5871(3) 0.5719(3) 1.1009(2) 0.0195(8) Uani 1 1 d . . . . .
C41 C 0.5092(3) 0.6063(3) 1.1546(2) 0.0243(9) Uani 1 1 d . . . . .
H41 H 0.4894 0.6786 1.1658 0.029 Uiso 1 1 calc R U . . .
C42 C 0.4603(3) 0.5327(3) 1.1918(2) 0.0254(9) Uani 1 1 d . . . . .
H42 H 0.4064 0.5550 1.2285 0.030 Uiso 1 1 calc R U . . .
C43 C 0.4896(3) 0.4276(3) 1.1759(2) 0.0262(9) Uani 1 1 d . . . . .
H43 H 0.4567 0.3790 1.2028 0.031 Uiso 1 1 calc R U . . .
C44 C 0.5667(3) 0.3925(3) 1.1210(2) 0.0237(9) Uani 1 1 d . . . . .
H44 H 0.5849 0.3196 1.1093 0.028 Uiso 1 1 calc R U . . .
C45 C 0.6168(3) 0.4641(3) 1.0835(2) 0.0192(8) Uani 1 1 d . . . . .
C46 C 0.9745(3) 0.5676(3) 0.9215(3) 0.0316(10) Uani 1 1 d . . . . .
H46A H 0.9820 0.6047 0.8777 0.047 Uiso 1 1 calc R U . . .
H46B H 1.0177 0.5053 0.9109 0.047 Uiso 1 1 calc R U . . .
H46C H 1.0029 0.6195 0.9790 0.047 Uiso 1 1 calc R U . . .
C47 C 0.8038(4) 0.7294(4) 0.8231(3) 0.0331(10) Uani 1 1 d . . . . .
H47A H 0.7821 0.6503 0.7941 0.050 Uiso 1 1 calc R U . . .
H47B H 0.8542 0.7594 0.7909 0.050 Uiso 1 1 calc R U . . .
H47C H 0.7367 0.7666 0.8257 0.050 Uiso 1 1 calc R U . . .
C48 C 0.6495(4) 0.9456(3) 1.0326(3) 0.0420(12) Uani 1 1 d . . . . .
H48A H 0.5730 0.9086 1.0090 0.063 Uiso 1 1 calc R U . . .
H48B H 0.6592 1.0158 1.0203 0.063 Uiso 1 1 calc R U . . .
H48C H 0.6630 0.9591 1.0952 0.063 Uiso 1 1 calc R U . . .
O1 O 0.8738(2) 1.0967(2) 0.42256(17) 0.0296(7) Uani 1 1 d . . . . .
O2 O 0.7136(2) 0.9909(2) 0.31228(17) 0.0320(7) Uani 1 1 d . . . . .
O3 O 1.0972(2) 0.6836(2) 0.20709(18) 0.0388(8) Uani 1 1 d . . . . .
O4 O 0.7434(2) 0.7516(2) 0.53042(16) 0.0258(6) Uani 1 1 d . . . . .
O5 O 0.6527(2) 0.6825(2) 0.65512(16) 0.0272(6) Uani 1 1 d . . . . .
O6 O 0.5164(2) 0.8007(2) 0.75022(17) 0.0330(7) Uani 1 1 d . . . . .
O7 O 0.7654(2) 0.2411(2) 1.08631(17) 0.0314(7) Uani 1 1 d . . . . .
O8 O 0.6093(2) 0.1882(2) 0.96445(19) 0.0333(7) Uani 1 1 d . . . . .
O9 O 0.9815(2) -0.0650(2) 0.77489(17) 0.0301(7) Uani 1 1 d . . . . .
O10 O 0.8584(2) 0.5283(2) 0.91682(16) 0.0228(6) Uani 1 1 d . . . . .
O11 O 0.8604(2) 0.7465(2) 0.90965(16) 0.0239(6) Uani 1 1 d . . . . .
O12 O 0.7277(2) 0.8771(2) 0.99342(18) 0.0292(7) Uani 1 1 d . . . . .
S1 S 0.80660(8) 0.99257(8) 0.37652(6) 0.0235(2) Uani 1 1 d . . . . .
S2 S 0.72485(8) 0.23307(8) 0.99805(6) 0.0231(2) Uani 1 1 d . . . . .
 
 
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
 
loop_
 _geom_bond_atom_site_label_1
 _geom_bond_atom_site_label_2
 _geom_bond_distance
 _geom_bond_site_symmetry_2
 _geom_bond_publ_flag
C1 C2 1.377(5) . ?
C1 C6 1.391(5) . ?
C1 S1 1.747(4) . ?
C2 C3 1.374(6) . ?
C2 H2 0.9500 . ?
C3 C4 1.384(5) . ?
C3 H3 0.9500 . ?
C4 O3 1.359(5) . ?
C4 C5 1.389(5) . ?
C5 C6 1.375(5) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 O3 1.446(5) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 C9 1.345(5) . ?
C8 S1 1.755(4) . ?
C8 H8 0.9500 . ?
C9 C10 1.483(5) . ?
C9 C21 1.496(5) . ?
C10 C15 1.390(5) . ?
C10 C11 1.397(5) . ?
C11 O4 1.368(4) . ?
C11 C12 1.396(5) . ?
C12 O5 1.381(4) . ?
C12 C13 1.401(5) . ?
C13 O6 1.363(4) . ?
C13 C14 1.393(5) . ?
C14 C15 1.392(5) . ?
C14 H14 0.9500 . ?
C15 C16 1.466(5) . ?
C16 C17 1.386(5) . ?
C16 C21 1.414(5) . ?
C17 C18 1.390(5) . ?
C17 H17 0.9500 . ?
C18 C19 1.390(6) . ?
C18 H18 0.9500 . ?
C19 C20 1.392(5) . ?
C19 H19 0.9500 . ?
C20 C21 1.380(5) . ?
C20 H20 0.9500 . ?
C22 O4 1.433(5) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 O5 1.427(5) . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 O6 1.436(5) . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C25 C30 1.390(5) . ?
C25 C26 1.394(5) . ?
C25 S2 1.749(4) . ?
C26 C27 1.381(5) . ?
C26 H26 0.9500 . ?
C27 C28 1.384(5) . ?
C27 H27 0.9500 . ?
C28 O9 1.361(4) . ?
C28 C29 1.394(5) . ?
C29 C30 1.372(5) . ?
C29 H29 0.9500 . ?
C30 H30 0.9500 . ?
C31 O9 1.428(5) . ?
C31 H31A 0.9800 . ?
C31 H31B 0.9800 . ?
C31 H31C 0.9800 . ?
C32 C33 1.338(5) . ?
C32 S2 1.757(4) . ?
C32 H32 0.9500 . ?
C33 C34 1.478(5) . ?
C33 C45 1.495(5) . ?
C34 C35 1.400(5) . ?
C34 C39 1.406(5) . ?
C35 O10 1.376(4) . ?
C35 C36 1.389(5) . ?
C36 O11 1.383(4) . ?
C36 C37 1.404(5) . ?
C37 O12 1.359(4) . ?
C37 C38 1.397(5) . ?
C38 C39 1.384(5) . ?
C38 H38 0.9500 . ?
C39 C40 1.466(5) . ?
C40 C41 1.386(5) . ?
C40 C45 1.417(5) . ?
C41 C42 1.394(5) . ?
C41 H41 0.9500 . ?
C42 C43 1.384(5) . ?
C42 H42 0.9500 . ?
C43 C44 1.393(5) . ?
C43 H43 0.9500 . ?
C44 C45 1.384(5) . ?
C44 H44 0.9500 . ?
C46 O10 1.438(4) . ?
C46 H46A 0.9800 . ?
C46 H46B 0.9800 . ?
C46 H46C 0.9800 . ?
C47 O11 1.442(4) . ?
C47 H47A 0.9800 . ?
C47 H47B 0.9800 . ?
C47 H47C 0.9800 . ?
C48 O12 1.434(5) . ?
C48 H48A 0.9800 . ?
C48 H48B 0.9800 . ?
C48 H48C 0.9800 . ?
O1 S1 1.440(3) . ?
O2 S1 1.439(3) . ?
O7 S2 1.441(3) . ?
O8 S2 1.441(3) . ?
 
loop_
 _geom_angle_atom_site_label_1
 _geom_angle_atom_site_label_2
 _geom_angle_atom_site_label_3
 _geom_angle
 _geom_angle_site_symmetry_1
 _geom_angle_site_symmetry_3
 _geom_angle_publ_flag
C2 C1 C6 119.8(4) . . ?
C2 C1 S1 119.8(3) . . ?
C6 C1 S1 120.4(3) . . ?
C3 C2 C1 120.5(4) . . ?
C3 C2 H2 119.7 . . ?
C1 C2 H2 119.7 . . ?
C2 C3 C4 119.7(4) . . ?
C2 C3 H3 120.2 . . ?
C4 C3 H3 120.2 . . ?
O3 C4 C3 124.2(4) . . ?
O3 C4 C5 115.6(3) . . ?
C3 C4 C5 120.2(4) . . ?
C6 C5 C4 119.7(4) . . ?
C6 C5 H5 120.1 . . ?
C4 C5 H5 120.1 . . ?
C5 C6 C1 120.0(4) . . ?
C5 C6 H6 120.0 . . ?
C1 C6 H6 120.0 . . ?
O3 C7 H7A 109.5 . . ?
O3 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
O3 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C9 C8 S1 127.2(3) . . ?
C9 C8 H8 116.4 . . ?
S1 C8 H8 116.4 . . ?
C8 C9 C10 123.4(3) . . ?
C8 C9 C21 131.6(3) . . ?
C10 C9 C21 104.9(3) . . ?
C15 C10 C11 119.7(3) . . ?
C15 C10 C9 109.5(3) . . ?
C11 C10 C9 130.8(3) . . ?
O4 C11 C12 120.1(3) . . ?
O4 C11 C10 121.2(3) . . ?
C12 C11 C10 118.7(3) . . ?
O5 C12 C11 119.5(3) . . ?
O5 C12 C13 119.4(3) . . ?
C11 C12 C13 121.0(3) . . ?
O6 C13 C14 123.6(3) . . ?
O6 C13 C12 116.1(3) . . ?
C14 C13 C12 120.3(3) . . ?
C15 C14 C13 118.1(3) . . ?
C15 C14 H14 120.9 . . ?
C13 C14 H14 120.9 . . ?
C10 C15 C14 122.1(3) . . ?
C10 C15 C16 108.9(3) . . ?
C14 C15 C16 129.0(3) . . ?
C17 C16 C21 121.0(3) . . ?
C17 C16 C15 130.6(3) . . ?
C21 C16 C15 108.4(3) . . ?
C16 C17 C18 118.5(3) . . ?
C16 C17 H17 120.7 . . ?
C18 C17 H17 120.7 . . ?
C17 C18 C19 120.5(4) . . ?
C17 C18 H18 119.7 . . ?
C19 C18 H18 119.7 . . ?
C18 C19 C20 121.1(4) . . ?
C18 C19 H19 119.5 . . ?
C20 C19 H19 119.5 . . ?
C21 C20 C19 118.9(3) . . ?
C21 C20 H20 120.5 . . ?
C19 C20 H20 120.5 . . ?
C20 C21 C16 119.9(3) . . ?
C20 C21 C9 131.8(3) . . ?
C16 C21 C9 108.3(3) . . ?
O4 C22 H22A 109.5 . . ?
O4 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
O4 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
O5 C23 H23A 109.5 . . ?
O5 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
O5 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
O6 C24 H24A 109.5 . . ?
O6 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
O6 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C30 C25 C26 119.7(3) . . ?
C30 C25 S2 119.7(3) . . ?
C26 C25 S2 120.4(3) . . ?
C27 C26 C25 120.4(3) . . ?
C27 C26 H26 119.8 . . ?
C25 C26 H26 119.8 . . ?
C26 C27 C28 119.6(3) . . ?
C26 C27 H27 120.2 . . ?
C28 C27 H27 120.2 . . ?
O9 C28 C27 125.0(3) . . ?
O9 C28 C29 115.2(3) . . ?
C27 C28 C29 119.9(3) . . ?
C30 C29 C28 120.6(4) . . ?
C30 C29 H29 119.7 . . ?
C28 C29 H29 119.7 . . ?
C29 C30 C25 119.8(4) . . ?
C29 C30 H30 120.1 . . ?
C25 C30 H30 120.1 . . ?
O9 C31 H31A 109.5 . . ?
O9 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
O9 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C33 C32 S2 125.9(3) . . ?
C33 C32 H32 117.0 . . ?
S2 C32 H32 117.0 . . ?
C32 C33 C34 124.4(3) . . ?
C32 C33 C45 130.1(3) . . ?
C34 C33 C45 105.4(3) . . ?
C35 C34 C39 118.9(3) . . ?
C35 C34 C33 131.9(3) . . ?
C39 C34 C33 109.2(3) . . ?
O10 C35 C36 122.9(3) . . ?
O10 C35 C34 117.7(3) . . ?
C36 C35 C34 119.3(3) . . ?
O11 C36 C35 120.3(3) . . ?
O11 C36 C37 119.0(3) . . ?
C35 C36 C37 120.7(3) . . ?
O12 C37 C38 124.5(3) . . ?
O12 C37 C36 114.6(3) . . ?
C38 C37 C36 120.9(3) . . ?
C39 C38 C37 117.7(3) . . ?
C39 C38 H38 121.2 . . ?
C37 C38 H38 121.2 . . ?
C38 C39 C34 122.5(3) . . ?
C38 C39 C40 128.8(3) . . ?
C34 C39 C40 108.6(3) . . ?
C41 C40 C45 121.0(3) . . ?
C41 C40 C39 130.5(3) . . ?
C45 C40 C39 108.5(3) . . ?
C40 C41 C42 118.7(3) . . ?
C40 C41 H41 120.6 . . ?
C42 C41 H41 120.6 . . ?
C43 C42 C41 120.7(4) . . ?
C43 C42 H42 119.7 . . ?
C41 C42 H42 119.7 . . ?
C42 C43 C44 120.6(4) . . ?
C42 C43 H43 119.7 . . ?
C44 C43 H43 119.7 . . ?
C45 C44 C43 119.8(3) . . ?
C45 C44 H44 120.1 . . ?
C43 C44 H44 120.1 . . ?
C44 C45 C40 119.1(3) . . ?
C44 C45 C33 132.6(3) . . ?
C40 C45 C33 108.3(3) . . ?
O10 C46 H46A 109.5 . . ?
O10 C46 H46B 109.5 . . ?
H46A C46 H46B 109.5 . . ?
O10 C46 H46C 109.5 . . ?
H46A C46 H46C 109.5 . . ?
H46B C46 H46C 109.5 . . ?
O11 C47 H47A 109.5 . . ?
O11 C47 H47B 109.5 . . ?
H47A C47 H47B 109.5 . . ?
O11 C47 H47C 109.5 . . ?
H47A C47 H47C 109.5 . . ?
H47B C47 H47C 109.5 . . ?
O12 C48 H48A 109.5 . . ?
O12 C48 H48B 109.5 . . ?
H48A C48 H48B 109.5 . . ?
O12 C48 H48C 109.5 . . ?
H48A C48 H48C 109.5 . . ?
H48B C48 H48C 109.5 . . ?
C4 O3 C7 117.1(3) . . ?
C11 O4 C22 114.4(3) . . ?
C12 O5 C23 113.3(3) . . ?
C13 O6 C24 116.1(3) . . ?
C28 O9 C31 118.2(3) . . ?
C35 O10 C46 117.7(3) . . ?
C36 O11 C47 111.8(3) . . ?
C37 O12 C48 115.8(3) . . ?
O2 S1 O1 118.05(17) . . ?
O2 S1 C1 108.32(17) . . ?
O1 S1 C1 108.69(17) . . ?
O2 S1 C8 109.55(17) . . ?
O1 S1 C8 108.88(17) . . ?
C1 S1 C8 102.17(18) . . ?
O7 S2 O8 117.54(18) . . ?
O7 S2 C25 108.25(17) . . ?
O8 S2 C25 107.42(17) . . ?
O7 S2 C32 108.89(17) . . ?
O8 S2 C32 108.56(17) . . ?
C25 S2 C32 105.53(17) . . ?
 
_refine_diff_density_max    0.565
_refine_diff_density_min   -0.540
_refine_diff_density_rms    0.085

_shelxl_version_number 2014/6





 
data_mo_181116LT_0m
 
_audit_creation_method            SHELXL-2014/6
_chemical_name_systematic         ?
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C26 H26 O7 S' 
_chemical_formula_weight          482.53

loop_
 _atom_type_symbol
 _atom_type_description
 _atom_type_scat_dispersion_real
 _atom_type_scat_dispersion_imag
 _atom_type_scat_source
 'C'  'C'   0.0033   0.0016
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'H'  'H'   0.0000   0.0000
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'O'  'O'   0.0106   0.0060
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'S'  'S'   0.1246   0.1234
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 
_space_group_crystal_system       monoclinic
_space_group_IT_number            14
_space_group_name_H-M_alt         'P 21/n'
_space_group_name_Hall            '-P 2yn'
 
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
 
loop_
 _space_group_symop_operation_xyz
 'x, y, z'
 '-x+1/2, y+1/2, -z+1/2'
 '-x, -y, -z'
 'x-1/2, -y-1/2, z-1/2'
 
_cell_length_a                    8.1007(8)
_cell_length_b                    25.249(3)
_cell_length_c                    11.9527(11)
_cell_angle_alpha                 90
_cell_angle_beta                  104.451(5)
_cell_angle_gamma                 90
_cell_volume                      2367.4(4)
_cell_formula_units_Z             4
_cell_measurement_temperature     100(2)
_cell_measurement_reflns_used     9907
_cell_measurement_theta_min       2.3872
_cell_measurement_theta_max       26.3485
 
_exptl_crystal_description        lump
_exptl_crystal_colour             red
_exptl_crystal_density_meas       'not measured'
_exptl_crystal_density_method     'not measured'
_exptl_crystal_density_diffrn     1.354          
_exptl_crystal_F_000              1016
_exptl_transmission_factor_min    ?
_exptl_transmission_factor_max    ?
_exptl_crystal_size_max           0.20
_exptl_crystal_size_mid           0.18
_exptl_crystal_size_min           0.12
_exptl_absorpt_coefficient_mu     0.182
_shelx_estimated_absorpt_T_min    ?
_shelx_estimated_absorpt_T_max    ?
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.7039  
_exptl_absorpt_correction_T_max   0.7454
_exptl_absorpt_process_details    'SADABS V2014/4 (Bruker AXS Inc.)'
_exptl_absorpt_special_details    ?
_diffrn_ambient_temperature       100(2)
_diffrn_radiation_wavelength      0.71073
_diffrn_radiation_type            MoK\a
_diffrn_source                    ?
_diffrn_measurement_device_type   'Bruker APEX-II CCD'
_diffrn_measurement_method        'φ and ω scans'
_diffrn_detector_area_resol_mean  8.3333
_diffrn_reflns_number             34172
_diffrn_reflns_av_unetI/netI      0.0206
_diffrn_reflns_av_R_equivalents   0.0313
_diffrn_reflns_limit_h_min        -7
_diffrn_reflns_limit_h_max        10
_diffrn_reflns_limit_k_min        -31
_diffrn_reflns_limit_k_max        31
_diffrn_reflns_limit_l_min        -14
_diffrn_reflns_limit_l_max        14
_diffrn_reflns_theta_min          1.613
_diffrn_reflns_theta_max          26.403
_diffrn_reflns_theta_full         25.242
_diffrn_measured_fraction_theta_max   0.998
_diffrn_measured_fraction_theta_full  1.000
_diffrn_reflns_Laue_measured_fraction_max    0.998
_diffrn_reflns_Laue_measured_fraction_full   1.000
_diffrn_reflns_point_group_measured_fraction_max   0.998
_diffrn_reflns_point_group_measured_fraction_full  1.000
_reflns_number_total              4834
_reflns_number_gt                 4215
_reflns_threshold_expression      'I > 2σ(I)'
_reflns_Friedel_coverage          0.000
_reflns_Friedel_fraction_max      .
_reflns_Friedel_fraction_full     .
 
_reflns_special_details
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
 
_computing_data_collection        'Bruker APEX2'
_computing_cell_refinement        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction         'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution     ?
_computing_structure_refinement   'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics     'Bruker SHELXTL'
_computing_publication_material   'Bruker SHELXTL'
_refine_special_details           ?
_refine_ls_structure_factor_coef  Fsqd
_refine_ls_matrix_type            full
_refine_ls_weighting_scheme       calc
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0366P)²+1.4257P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary      ?
_atom_sites_solution_secondary    ?
_atom_sites_solution_hydrogens    geom
_refine_ls_hydrogen_treatment     constr
_refine_ls_extinction_method      none
_refine_ls_extinction_coef        .
_refine_ls_number_reflns          4834
_refine_ls_number_parameters      313
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0418
_refine_ls_R_factor_gt            0.0345
_refine_ls_wR_factor_ref          0.0867
_refine_ls_wR_factor_gt           0.0824
_refine_ls_goodness_of_fit_ref    1.055
_refine_ls_restrained_S_all       1.055
_refine_ls_shift/su_max           0.004
_refine_ls_shift/su_mean          0.000
 
loop_
 _atom_site_label
 _atom_site_type_symbol
 _atom_site_fract_x
 _atom_site_fract_y
 _atom_site_fract_z
 _atom_site_U_iso_or_equiv
 _atom_site_adp_type
 _atom_site_occupancy
 _atom_site_site_symmetry_order  
 _atom_site_calc_flag
 _atom_site_refinement_flags_posn
 _atom_site_refinement_flags_adp
 _atom_site_refinement_flags_occupancy
 _atom_site_disorder_assembly
 _atom_site_disorder_group
S1 S 0.68617(5) 0.66773(2) 0.13809(3) 0.01628(10) Uani 1 1 d . . . . .
O1 O 0.47353(14) 0.36675(4) 0.33343(9) 0.0204(2) Uani 1 1 d . . . . .
O2 O 0.57225(14) 0.70883(4) 0.15680(10) 0.0238(2) Uani 1 1 d . . . . .
O3 O 0.75228(13) 0.53274(4) 0.40044(8) 0.0172(2) Uani 1 1 d . . . . .
O4 O 0.69765(13) 0.43091(4) 0.46935(9) 0.0201(2) Uani 1 1 d . . . . .
O5 O -0.00288(13) 0.52891(4) -0.22278(9) 0.0207(2) Uani 1 1 d . . . . .
O6 O 0.10831(14) 0.62452(4) -0.20313(9) 0.0224(2) Uani 1 1 d . . . . .
O7 O 0.69116(14) 0.65714(5) 0.02033(9) 0.0235(3) Uani 1 1 d . . . . .
C1 C 1.4044(2) 0.71096(8) 0.42196(16) 0.0341(4) Uani 1 1 d . . . . .
H26 H 1.4105 0.7455 0.4603 0.051 Uiso 1 1 calc R U . . .
H1 H 1.4839 0.7104 0.3722 0.051 Uiso 1 1 calc R U . . .
H3 H 1.4351 0.6830 0.4803 0.051 Uiso 1 1 calc R U . . .
C2 C 1.2257(2) 0.70177(6) 0.34979(14) 0.0228(3) Uani 1 1 d . . . . .
C3 C 1.0851(2) 0.71572(6) 0.39103(14) 0.0227(3) Uani 1 1 d . . . . .
H4 H 1.1026 0.7319 0.4648 0.027 Uiso 1 1 calc R U . . .
C4 C 0.9202(2) 0.70635(6) 0.32620(13) 0.0195(3) Uani 1 1 d . . . . .
H5 H 0.8253 0.7159 0.3552 0.023 Uiso 1 1 calc R U . . .
C5 C 0.89564(19) 0.68276(6) 0.21803(13) 0.0168(3) Uani 1 1 d . . . . .
C6 C 0.64853(18) 0.60935(6) 0.20645(12) 0.0160(3) Uani 1 1 d . . . . .
H6 H 0.7179 0.6039 0.2823 0.019 Uiso 1 1 calc R U . . .
C7 C 0.53356(18) 0.57113(6) 0.16504(12) 0.0145(3) Uani 1 1 d . . . . .
C8 C 0.53330(18) 0.51958(6) 0.22378(12) 0.0147(3) Uani 1 1 d . . . . .
C9 C 0.63178(17) 0.50096(6) 0.32909(12) 0.0151(3) Uani 1 1 d . . . . .
C10 C 0.60899(18) 0.44918(6) 0.36255(12) 0.0158(3) Uani 1 1 d . . . . .
C11 C 0.48690(18) 0.41617(6) 0.29108(12) 0.0159(3) Uani 1 1 d . . . . .
C12 C 0.3343(2) 0.33458(6) 0.27166(14) 0.0260(4) Uani 1 1 d . . . . .
H2 H 0.2267 0.3534 0.2656 0.039 Uiso 1 1 calc R U . . .
H13 H 0.3329 0.3012 0.3132 0.039 Uiso 1 1 calc R U . . .
H14 H 0.3483 0.3272 0.1941 0.039 Uiso 1 1 calc R U . . .
C13 C 0.39505(17) 0.56724(6) 0.05777(12) 0.0146(3) Uani 1 1 d . . . . .
C14 C 0.32718(17) 0.51616(6) 0.04971(12) 0.0141(3) Uani 1 1 d . . . . .
C15 C 0.41334(17) 0.48588(6) 0.15318(12) 0.0139(3) Uani 1 1 d . . . . .
C16 C 0.6890(2) 0.55618(7) 0.49165(14) 0.0244(4) Uani 1 1 d . . . . .
H7 H 0.5922 0.5793 0.4580 0.037 Uiso 1 1 calc R U . . .
H8 H 0.7797 0.5770 0.5422 0.037 Uiso 1 1 calc R U . . .
H9 H 0.6521 0.5281 0.5367 0.037 Uiso 1 1 calc R U . . .
C17 C 0.8656(2) 0.41313(8) 0.47138(15) 0.0312(4) Uani 1 1 d . . . . .
H10 H 0.8590 0.3835 0.4175 0.047 Uiso 1 1 calc R U . . .
H12 H 0.9230 0.4015 0.5496 0.047 Uiso 1 1 calc R U . . .
H11 H 0.9303 0.4422 0.4484 0.047 Uiso 1 1 calc R U . . .
C18 C 0.38789(18) 0.43459(6) 0.18498(12) 0.0152(3) Uani 1 1 d . . . . .
H15 H 0.3056 0.4124 0.1363 0.018 Uiso 1 1 calc R U . . .
C19 C 0.19428(17) 0.50097(6) -0.04325(12) 0.0146(3) Uani 1 1 d . . . . .
H23 H 0.1513 0.4658 -0.0490 0.018 Uiso 1 1 calc R U . . .
C20 C 0.12596(18) 0.53844(6) -0.12742(12) 0.0162(3) Uani 1 1 d . . . . .
C21 C -0.05916(19) 0.47528(6) -0.24286(13) 0.0203(3) Uani 1 1 d . . . . .
H18 H 0.0367 0.4529 -0.2498 0.031 Uiso 1 1 calc R U . . .
H17 H -0.1498 0.4733 -0.3145 0.031 Uiso 1 1 calc R U . . .
H16 H -0.1029 0.4629 -0.1781 0.031 Uiso 1 1 calc R U . . .
C22 C 0.18960(18) 0.59087(6) -0.11686(12) 0.0166(3) Uani 1 1 d . . . . .
C23 C 0.1753(2) 0.67681(6) -0.20021(15) 0.0271(4) Uani 1 1 d . . . . .
H19 H 0.1694 0.6941 -0.1279 0.041 Uiso 1 1 calc R U . . .
H21 H 0.1083 0.6971 -0.2659 0.041 Uiso 1 1 calc R U . . .
H20 H 0.2943 0.6752 -0.2048 0.041 Uiso 1 1 calc R U . . .
C24 C 0.32445(18) 0.60523(6) -0.02541(12) 0.0165(3) Uani 1 1 d . . . . .
H22 H 0.3681 0.6403 -0.0194 0.020 Uiso 1 1 calc R U . . .
C25 C 1.0334(2) 0.66868(6) 0.17485(13) 0.0211(3) Uani 1 1 d . . . . .
H24 H 1.0157 0.6525 0.1010 0.025 Uiso 1 1 calc R U . . .
C26 C 1.1976(2) 0.67848(7) 0.24097(14) 0.0243(3) Uani 1 1 d . . . . .
H25 H 1.2923 0.6692 0.2115 0.029 Uiso 1 1 calc R U . . .
 
 
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
 
loop_
 _geom_bond_atom_site_label_1
 _geom_bond_atom_site_label_2
 _geom_bond_distance
 _geom_bond_site_symmetry_2
 _geom_bond_publ_flag
S1 O2 1.4426(11) . ?
S1 O7 1.4432(11) . ?
S1 C6 1.7488(15) . ?
S1 C5 1.7683(15) . ?
O1 C11 1.3612(18) . ?
O1 C12 1.4357(18) . ?
O3 C9 1.3816(17) . ?
O3 C16 1.4424(18) . ?
O4 C10 1.3786(17) . ?
O4 C17 1.4274(19) . ?
O5 C20 1.3611(17) . ?
O5 C21 1.4299(18) . ?
O6 C22 1.3711(17) . ?
O6 C23 1.4246(19) . ?
C1 C2 1.507(2) . ?
C1 H26 0.9800 . ?
C1 H1 0.9800 . ?
C1 H3 0.9800 . ?
C2 C26 1.393(2) . ?
C2 C3 1.395(2) . ?
C3 C4 1.388(2) . ?
C3 H4 0.9500 . ?
C4 C5 1.392(2) . ?
C4 H5 0.9500 . ?
C5 C25 1.388(2) . ?
C6 C7 1.347(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.479(2) . ?
C7 C13 1.4813(19) . ?
C8 C9 1.393(2) . ?
C8 C15 1.404(2) . ?
C9 C10 1.393(2) . ?
C10 C11 1.407(2) . ?
C11 C18 1.400(2) . ?
C12 H2 0.9800 . ?
C12 H13 0.9800 . ?
C12 H14 0.9800 . ?
C13 C14 1.396(2) . ?
C13 C24 1.397(2) . ?
C14 C19 1.3941(19) . ?
C14 C15 1.4732(19) . ?
C15 C18 1.380(2) . ?
C16 H7 0.9800 . ?
C16 H8 0.9800 . ?
C16 H9 0.9800 . ?
C17 H10 0.9800 . ?
C17 H12 0.9800 . ?
C17 H11 0.9800 . ?
C18 H15 0.9500 . ?
C19 C20 1.391(2) . ?
C19 H23 0.9500 . ?
C20 C22 1.415(2) . ?
C21 H18 0.9800 . ?
C21 H17 0.9800 . ?
C21 H16 0.9800 . ?
C22 C24 1.387(2) . ?
C23 H19 0.9800 . ?
C23 H21 0.9800 . ?
C23 H20 0.9800 . ?
C24 H22 0.9500 . ?
C25 C26 1.389(2) . ?
C25 H24 0.9500 . ?
C26 H25 0.9500 . ?
 
loop_
 _geom_angle_atom_site_label_1
 _geom_angle_atom_site_label_2
 _geom_angle_atom_site_label_3
 _geom_angle
 _geom_angle_site_symmetry_1
 _geom_angle_site_symmetry_3
 _geom_angle_publ_flag
O2 S1 O7 117.33(7) . . ?
O2 S1 C6 109.94(7) . . ?
O7 S1 C6 110.49(7) . . ?
O2 S1 C5 109.07(7) . . ?
O7 S1 C5 108.07(7) . . ?
C6 S1 C5 100.60(7) . . ?
C11 O1 C12 116.91(12) . . ?
C9 O3 C16 112.04(11) . . ?
C10 O4 C17 113.27(11) . . ?
C20 O5 C21 116.98(12) . . ?
C22 O6 C23 116.58(12) . . ?
C2 C1 H26 109.5 . . ?
C2 C1 H1 109.5 . . ?
H26 C1 H1 109.5 . . ?
C2 C1 H3 109.5 . . ?
H26 C1 H3 109.5 . . ?
H1 C1 H3 109.5 . . ?
C26 C2 C3 118.61(14) . . ?
C26 C2 C1 120.62(16) . . ?
C3 C2 C1 120.77(15) . . ?
C4 C3 C2 121.15(15) . . ?
C4 C3 H4 119.4 . . ?
C2 C3 H4 119.4 . . ?
C3 C4 C5 119.08(15) . . ?
C3 C4 H5 120.5 . . ?
C5 C4 H5 120.5 . . ?
C25 C5 C4 120.90(14) . . ?
C25 C5 S1 119.77(11) . . ?
C4 C5 S1 119.27(12) . . ?
C7 C6 S1 128.14(12) . . ?
C7 C6 H6 115.9 . . ?
S1 C6 H6 115.9 . . ?
C6 C7 C8 122.61(13) . . ?
C6 C7 C13 132.10(14) . . ?
C8 C7 C13 105.20(12) . . ?
C9 C8 C15 119.52(13) . . ?
C9 C8 C7 131.12(13) . . ?
C15 C8 C7 109.32(12) . . ?
O3 C9 C10 119.47(12) . . ?
O3 C9 C8 121.24(13) . . ?
C10 C9 C8 119.29(13) . . ?
O4 C10 C9 120.28(13) . . ?
O4 C10 C11 119.25(13) . . ?
C9 C10 C11 120.33(13) . . ?
O1 C11 C18 124.10(13) . . ?
O1 C11 C10 115.23(13) . . ?
C18 C11 C10 120.67(14) . . ?
O1 C12 H2 109.5 . . ?
O1 C12 H13 109.5 . . ?
H2 C12 H13 109.5 . . ?
O1 C12 H14 109.5 . . ?
H2 C12 H14 109.5 . . ?
H13 C12 H14 109.5 . . ?
C14 C13 C24 120.07(13) . . ?
C14 C13 C7 108.72(12) . . ?
C24 C13 C7 131.13(14) . . ?
C19 C14 C13 121.44(13) . . ?
C19 C14 C15 129.51(14) . . ?
C13 C14 C15 109.01(12) . . ?
C18 C15 C8 122.14(13) . . ?
C18 C15 C14 130.27(13) . . ?
C8 C15 C14 107.57(13) . . ?
O3 C16 H7 109.5 . . ?
O3 C16 H8 109.5 . . ?
H7 C16 H8 109.5 . . ?
O3 C16 H9 109.5 . . ?
H7 C16 H9 109.5 . . ?
H8 C16 H9 109.5 . . ?
O4 C17 H10 109.5 . . ?
O4 C17 H12 109.5 . . ?
H10 C17 H12 109.5 . . ?
O4 C17 H11 109.5 . . ?
H10 C17 H11 109.5 . . ?
H12 C17 H11 109.5 . . ?
C15 C18 C11 118.05(13) . . ?
C15 C18 H15 121.0 . . ?
C11 C18 H15 121.0 . . ?
C20 C19 C14 118.56(14) . . ?
C20 C19 H23 120.7 . . ?
C14 C19 H23 120.7 . . ?
O5 C20 C19 124.67(13) . . ?
O5 C20 C22 115.23(13) . . ?
C19 C20 C22 120.09(13) . . ?
O5 C21 H18 109.5 . . ?
O5 C21 H17 109.5 . . ?
H18 C21 H17 109.5 . . ?
O5 C21 H16 109.5 . . ?
H18 C21 H16 109.5 . . ?
H17 C21 H16 109.5 . . ?
O6 C22 C24 124.52(14) . . ?
O6 C22 C20 114.64(13) . . ?
C24 C22 C20 120.85(13) . . ?
O6 C23 H19 109.5 . . ?
O6 C23 H21 109.5 . . ?
H19 C23 H21 109.5 . . ?
O6 C23 H20 109.5 . . ?
H19 C23 H20 109.5 . . ?
H21 C23 H20 109.5 . . ?
C22 C24 C13 118.91(14) . . ?
C22 C24 H22 120.5 . . ?
C13 C24 H22 120.5 . . ?
C5 C25 C26 119.17(14) . . ?
C5 C25 H24 120.4 . . ?
C26 C25 H24 120.4 . . ?
C25 C26 C2 121.10(15) . . ?
C25 C26 H25 119.4 . . ?
C2 C26 H25 119.4 . . ?
 
_refine_diff_density_max    0.401
_refine_diff_density_min   -0.381
_refine_diff_density_rms    0.044

_shelxl_version_number 2014/6



 
data_181119LT_a
 
_audit_creation_method            SHELXL-2014/6
_chemical_name_systematic         ?
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C20 H22 O7 S' 
_chemical_formula_weight          406.43

loop_
 _atom_type_symbol
 _atom_type_description
 _atom_type_scat_dispersion_real
 _atom_type_scat_dispersion_imag
 _atom_type_scat_source
 'C'  'C'   0.0033   0.0016
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'H'  'H'   0.0000   0.0000
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'O'  'O'   0.0106   0.0060
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'S'  'S'   0.1246   0.1234
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 
_space_group_crystal_system       monoclinic
_space_group_IT_number            14
_space_group_name_H-M_alt         'P 21/c'
_space_group_name_Hall            '-P 2ybc'
 
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
 
loop_
 _space_group_symop_operation_xyz
 'x, y, z'
 '-x, y+1/2, -z+1/2'
 '-x, -y, -z'
 'x, -y-1/2, z-1/2'
 
_cell_length_a                    19.3636(3)
_cell_length_b                    13.1724(2)
_cell_length_c                    14.6482(3)
_cell_angle_alpha                 90
_cell_angle_beta                  96.8350(10)
_cell_angle_gamma                 90
_cell_volume                      3709.69(11)
_cell_formula_units_Z             8
_cell_measurement_temperature     100(2)
_cell_measurement_reflns_used     9944
_cell_measurement_theta_min       2.4139
_cell_measurement_theta_max       26.3866
 
_exptl_crystal_description        lump
_exptl_crystal_colour             orange
_exptl_crystal_density_meas       'not measured'
_exptl_crystal_density_method     'not measured'
_exptl_crystal_density_diffrn     1.455          
_exptl_crystal_F_000              1712
_exptl_transmission_factor_min    ?
_exptl_transmission_factor_max    ?
_exptl_crystal_size_max           0.20
_exptl_crystal_size_mid           0.15
_exptl_crystal_size_min           0.15
_exptl_absorpt_coefficient_mu     0.216
_shelx_estimated_absorpt_T_min    ?
_shelx_estimated_absorpt_T_max    ?
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.7126  
_exptl_absorpt_correction_T_max   0.7454
_exptl_absorpt_process_details    'SADABS V2014/4 (Bruker AXS Inc.)'
_exptl_absorpt_special_details    ?
_diffrn_ambient_temperature       100(2)
_diffrn_radiation_wavelength      0.71073
_diffrn_radiation_type            MoK\a
_diffrn_source                    ?
_diffrn_measurement_device_type   'Bruker APEX-II CCD'
_diffrn_measurement_method        'φ and ω scans'
_diffrn_detector_area_resol_mean  8.3333
_diffrn_reflns_number             33154
_diffrn_reflns_av_unetI/netI      0.0238
_diffrn_reflns_av_R_equivalents   0.0277
_diffrn_reflns_limit_h_min        -17
_diffrn_reflns_limit_h_max        24
_diffrn_reflns_limit_k_min        -14
_diffrn_reflns_limit_k_max        16
_diffrn_reflns_limit_l_min        -18
_diffrn_reflns_limit_l_max        18
_diffrn_reflns_theta_min          1.874
_diffrn_reflns_theta_max          26.394
_diffrn_reflns_theta_full         25.242
_diffrn_measured_fraction_theta_max   0.999
_diffrn_measured_fraction_theta_full  1.000
_diffrn_reflns_Laue_measured_fraction_max    0.999
_diffrn_reflns_Laue_measured_fraction_full   1.000
_diffrn_reflns_point_group_measured_fraction_max   0.999
_diffrn_reflns_point_group_measured_fraction_full  1.000
_reflns_number_total              7607
_reflns_number_gt                 6550
_reflns_threshold_expression      'I > 2σ(I)'
_reflns_Friedel_coverage          0.000
_reflns_Friedel_fraction_max      .
_reflns_Friedel_fraction_full     .
 
_reflns_special_details
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
 
_computing_data_collection        'Bruker APEX2'
_computing_cell_refinement        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction         'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution     ?
_computing_structure_refinement   'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics     'Bruker SHELXTL'
_computing_publication_material   'Bruker SHELXTL'
_refine_special_details           ?
_refine_ls_structure_factor_coef  Fsqd
_refine_ls_matrix_type            full
_refine_ls_weighting_scheme       calc
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0462P)²+1.7459P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary      ?
_atom_sites_solution_secondary    ?
_atom_sites_solution_hydrogens    geom
_refine_ls_hydrogen_treatment     constr
_refine_ls_extinction_method      none
_refine_ls_extinction_coef        .
_refine_ls_number_reflns          7607
_refine_ls_number_parameters      517
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0395
_refine_ls_R_factor_gt            0.0329
_refine_ls_wR_factor_ref          0.0921
_refine_ls_wR_factor_gt           0.0877
_refine_ls_goodness_of_fit_ref    1.035
_refine_ls_restrained_S_all       1.035
_refine_ls_shift/su_max           0.002
_refine_ls_shift/su_mean          0.000
 
loop_
 _atom_site_label
 _atom_site_type_symbol
 _atom_site_fract_x
 _atom_site_fract_y
 _atom_site_fract_z
 _atom_site_U_iso_or_equiv
 _atom_site_adp_type
 _atom_site_occupancy
 _atom_site_site_symmetry_order  
 _atom_site_calc_flag
 _atom_site_refinement_flags_posn
 _atom_site_refinement_flags_adp
 _atom_site_refinement_flags_occupancy
 _atom_site_disorder_assembly
 _atom_site_disorder_group
S1 S 0.54710(2) 0.45740(3) 0.62854(2) 0.01444(9) Uani 1 1 d . . . . .
S2 S 0.04749(2) 0.23081(3) 0.60998(2) 0.01480(9) Uani 1 1 d . . . . .
O1 O 0.80885(5) 0.32185(7) 0.61350(7) 0.0180(2) Uani 1 1 d . . . . .
O2 O 0.61694(5) 0.99356(7) 0.62636(7) 0.0180(2) Uani 1 1 d . . . . .
O3 O 0.75450(5) 1.00474(8) 0.66394(8) 0.0198(2) Uani 1 1 d . . . . .
O4 O 0.55162(5) 0.80567(8) 0.58253(7) 0.0165(2) Uani 1 1 d . . . . .
O5 O 0.90942(5) 0.44947(8) 0.64413(8) 0.0192(2) Uani 1 1 d . . . . .
O6 O 0.58001(5) 0.41978(8) 0.71583(7) 0.0192(2) Uani 1 1 d . . . . .
O7 O 0.55536(5) 0.39480(8) 0.54936(7) 0.0199(2) Uani 1 1 d . . . . .
O8 O 0.25612(5) -0.31113(7) 0.69178(7) 0.0189(2) Uani 1 1 d . . . . .
O9 O 0.31046(5) 0.36588(7) 0.60885(8) 0.0190(2) Uani 1 1 d . . . . .
O10 O 0.11870(5) -0.30213(8) 0.65559(7) 0.0180(2) Uani 1 1 d . . . . .
O11 O 0.41083(5) 0.23877(8) 0.64132(8) 0.0196(2) Uani 1 1 d . . . . .
O12 O 0.05280(5) -0.11689(8) 0.59442(7) 0.0169(2) Uani 1 1 d . . . . .
O13 O 0.05367(5) 0.28909(8) 0.52796(8) 0.0226(2) Uani 1 1 d . . . . .
O14 O 0.07992(5) 0.27320(8) 0.69551(7) 0.0209(2) Uani 1 1 d . . . . .
C1 C 0.75606(8) 0.25263(11) 0.57731(11) 0.0210(3) Uani 1 1 d . . . . .
H13 H 0.7251 0.2386 0.6240 0.031 Uiso 1 1 calc R U . . .
H14 H 0.7776 0.1892 0.5601 0.031 Uiso 1 1 calc R U . . .
H1 H 0.7292 0.2825 0.5230 0.031 Uiso 1 1 calc R U . . .
C2 C 0.78896(7) 0.42082(11) 0.62347(10) 0.0142(3) Uani 1 1 d . . . . .
C3 C 0.72057(7) 0.45324(11) 0.61734(9) 0.0139(3) Uani 1 1 d . . . . .
H15 H 0.6834 0.4058 0.6078 0.017 Uiso 1 1 calc R U . . .
C4 C 0.70708(7) 0.55692(11) 0.62536(9) 0.0133(3) Uani 1 1 d . . . . .
C5 C 0.64080(7) 0.61445(11) 0.61563(9) 0.0130(3) Uani 1 1 d . . . . .
C6 C 0.66147(7) 0.72303(11) 0.61795(9) 0.0128(3) Uani 1 1 d . . . . .
C7 C 0.62183(7) 0.81166(11) 0.61081(9) 0.0135(3) Uani 1 1 d . . . . .
C8 C 0.65543(7) 0.90515(11) 0.62689(10) 0.0148(3) Uani 1 1 d . . . . .
C9 C 0.61803(8) 1.05387(12) 0.54515(11) 0.0235(3) Uani 1 1 d . . . . .
H2 H 0.6657 1.0575 0.5291 0.035 Uiso 1 1 calc R U . . .
H5 H 0.6014 1.1225 0.5564 0.035 Uiso 1 1 calc R U . . .
H4 H 0.5878 1.0229 0.4943 0.035 Uiso 1 1 calc R U . . .
C10 C 0.82853(7) 1.01465(12) 0.67840(12) 0.0224(3) Uani 1 1 d . . . . .
H3 H 0.8475 0.9686 0.7277 0.034 Uiso 1 1 calc R U . . .
H22 H 0.8409 1.0848 0.6958 0.034 Uiso 1 1 calc R U . . .
H21 H 0.8480 0.9974 0.6216 0.034 Uiso 1 1 calc R U . . .
C11 C 0.72835(7) 0.90942(11) 0.64768(10) 0.0156(3) Uani 1 1 d . . . . .
C12 C 0.50677(7) 0.84185(12) 0.64706(11) 0.0201(3) Uani 1 1 d . . . . .
H7 H 0.5246 0.8189 0.7090 0.030 Uiso 1 1 calc R U . . .
H6 H 0.4597 0.8151 0.6304 0.030 Uiso 1 1 calc R U . . .
H8 H 0.5055 0.9162 0.6457 0.030 Uiso 1 1 calc R U . . .
C13 C 0.73402(7) 0.72939(11) 0.63693(9) 0.0136(3) Uani 1 1 d . . . . .
C14 C 0.76827(7) 0.82118(11) 0.65112(10) 0.0156(3) Uani 1 1 d . . . . .
H9 H 0.8175 0.8240 0.6629 0.019 Uiso 1 1 calc R U . . .
C15 C 0.76219(7) 0.62595(11) 0.63884(9) 0.0134(3) Uani 1 1 d . . . . .
C16 C 0.83106(7) 0.59409(11) 0.64732(10) 0.0151(3) Uani 1 1 d . . . . .
H20 H 0.8681 0.6415 0.6582 0.018 Uiso 1 1 calc R U . . .
C17 C 0.84429(7) 0.49097(11) 0.63950(10) 0.0150(3) Uani 1 1 d . . . . .
C18 C 0.96658(7) 0.51824(12) 0.64556(13) 0.0261(4) Uani 1 1 d . . . . .
H10 H 0.9593 0.5631 0.5919 0.039 Uiso 1 1 calc R U . . .
H11 H 1.0097 0.4798 0.6438 0.039 Uiso 1 1 calc R U . . .
H12 H 0.9699 0.5590 0.7019 0.039 Uiso 1 1 calc R U . . .
C19 C 0.57453(7) 0.58220(11) 0.61158(10) 0.0141(3) Uani 1 1 d . . . . .
H19 H 0.5392 0.6319 0.5982 0.017 Uiso 1 1 calc R U . . .
C20 C 0.45789(7) 0.47370(12) 0.63639(11) 0.0191(3) Uani 1 1 d . . . . .
H16 H 0.4355 0.4071 0.6384 0.029 Uiso 1 1 calc R U . . .
H17 H 0.4365 0.5115 0.5827 0.029 Uiso 1 1 calc R U . . .
H18 H 0.4518 0.5116 0.6925 0.029 Uiso 1 1 calc R U . . .
C21 C 0.33016(7) -0.31974(12) 0.70970(11) 0.0213(3) Uani 1 1 d . . . . .
H26 H 0.3508 -0.3099 0.6524 0.032 Uiso 1 1 calc R U . . .
H27 H 0.3424 -0.3873 0.7346 0.032 Uiso 1 1 calc R U . . .
H23 H 0.3480 -0.2679 0.7544 0.032 Uiso 1 1 calc R U . . .
C22 C 0.22961(7) -0.21820(11) 0.66549(10) 0.0147(3) Uani 1 1 d . . . . .
C23 C 0.26988(7) -0.13135(11) 0.65820(9) 0.0140(3) Uani 1 1 d . . . . .
H42 H 0.3192 -0.1340 0.6693 0.017 Uiso 1 1 calc R U . . .
C24 C 0.23563(7) -0.04125(11) 0.63422(9) 0.0132(3) Uani 1 1 d . . . . .
C25 C 0.26370(7) 0.06168(10) 0.62969(9) 0.0128(3) Uani 1 1 d . . . . .
C26 C 0.20859(7) 0.13048(11) 0.61246(9) 0.0131(3) Uani 1 1 d . . . . .
C27 C 0.22206(7) 0.23371(11) 0.60451(10) 0.0141(3) Uani 1 1 d . . . . .
H34 H 0.1849 0.2807 0.5922 0.017 Uiso 1 1 calc R U . . .
C28 C 0.29049(7) 0.26690(10) 0.61483(10) 0.0145(3) Uani 1 1 d . . . . .
C29 C 0.25659(8) 0.44022(11) 0.60081(11) 0.0187(3) Uani 1 1 d . . . . .
H28 H 0.2251 0.4280 0.5444 0.028 Uiso 1 1 calc R U . . .
H24 H 0.2771 0.5080 0.5984 0.028 Uiso 1 1 calc R U . . .
H29 H 0.2306 0.4357 0.6541 0.028 Uiso 1 1 calc R U . . .
C30 C 0.11969(8) -0.37317(11) 0.58129(11) 0.0212(3) Uani 1 1 d . . . . .
H43 H 0.0836 -0.3549 0.5313 0.032 Uiso 1 1 calc R U . . .
H25 H 0.1108 -0.4417 0.6032 0.032 Uiso 1 1 calc R U . . .
H44 H 0.1653 -0.3714 0.5588 0.032 Uiso 1 1 calc R U . . .
C31 C 0.15664(7) -0.21500(11) 0.64570(10) 0.0143(3) Uani 1 1 d . . . . .
C32 C 0.34587(7) 0.19693(11) 0.63287(10) 0.0142(3) Uani 1 1 d . . . . .
C33 C 0.46846(7) 0.17079(11) 0.64590(11) 0.0200(3) Uani 1 1 d . . . . .
H30 H 0.4696 0.1289 0.7013 0.030 Uiso 1 1 calc R U . . .
H32 H 0.5117 0.2098 0.6481 0.030 Uiso 1 1 calc R U . . .
H31 H 0.4636 0.1270 0.5914 0.030 Uiso 1 1 calc R U . . .
C34 C 0.33246(7) 0.09420(11) 0.64088(9) 0.0142(3) Uani 1 1 d . . . . .
H33 H 0.3695 0.0470 0.6537 0.017 Uiso 1 1 calc R U . . .
C35 C 0.14247(7) 0.07288(11) 0.60520(9) 0.0134(3) Uani 1 1 d . . . . .
C36 C 0.16306(7) -0.03553(11) 0.61559(9) 0.0130(3) Uani 1 1 d . . . . .
C37 C 0.12312(7) -0.12345(11) 0.62024(9) 0.0134(3) Uani 1 1 d . . . . .
C38 C 0.00690(7) -0.15846(12) 0.65569(11) 0.0198(3) Uani 1 1 d . . . . .
H35 H 0.0003 -0.2312 0.6434 0.030 Uiso 1 1 calc R U . . .
H37 H -0.0381 -0.1238 0.6457 0.030 Uiso 1 1 calc R U . . .
H36 H 0.0274 -0.1486 0.7195 0.030 Uiso 1 1 calc R U . . .
C39 C 0.07608(7) 0.10550(11) 0.59866(10) 0.0149(3) Uani 1 1 d . . . . .
H41 H 0.0410 0.0552 0.5866 0.018 Uiso 1 1 calc R U . . .
C40 C -0.04142(7) 0.21103(12) 0.61961(11) 0.0188(3) Uani 1 1 d . . . . .
H40 H -0.0646 0.2767 0.6239 0.028 Uiso 1 1 calc R U . . .
H38 H -0.0461 0.1711 0.6750 0.028 Uiso 1 1 calc R U . . .
H39 H -0.0630 0.1743 0.5654 0.028 Uiso 1 1 calc R U . . .
 
 
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
 
loop_
 _geom_bond_atom_site_label_1
 _geom_bond_atom_site_label_2
 _geom_bond_distance
 _geom_bond_site_symmetry_2
 _geom_bond_publ_flag
S1 O6 1.4466(11) . ?
S1 O7 1.4475(11) . ?
S1 C19 1.7544(14) . ?
S1 C20 1.7581(14) . ?
S2 O13 1.4427(11) . ?
S2 O14 1.4451(11) . ?
S2 C39 1.7552(14) . ?
S2 C40 1.7635(14) . ?
O1 C2 1.3722(17) . ?
O1 C1 1.4242(17) . ?
O2 C8 1.3821(17) . ?
O2 C9 1.4327(18) . ?
O3 C11 1.3641(17) . ?
O3 C10 1.4299(17) . ?
O4 C7 1.3756(16) . ?
O4 C12 1.4388(17) . ?
O5 C17 1.3688(16) . ?
O5 C18 1.4284(17) . ?
O8 C22 1.3649(17) . ?
O8 C21 1.4311(17) . ?
O9 C28 1.3658(17) . ?
O9 C29 1.4254(17) . ?
O10 C31 1.3796(16) . ?
O10 C30 1.4371(18) . ?
O11 C32 1.3653(16) . ?
O11 C33 1.4261(16) . ?
O12 C37 1.3718(16) . ?
O12 C38 1.4440(16) . ?
C1 H13 0.9800 . ?
C1 H14 0.9800 . ?
C1 H1 0.9800 . ?
C2 C3 1.3841(19) . ?
C2 C17 1.4132(19) . ?
C3 C4 1.398(2) . ?
C3 H15 0.9500 . ?
C4 C15 1.3980(19) . ?
C4 C5 1.4826(18) . ?
C5 C19 1.3464(19) . ?
C5 C6 1.4845(19) . ?
C6 C7 1.3942(19) . ?
C6 C13 1.4017(18) . ?
C7 C8 1.400(2) . ?
C8 C11 1.4098(19) . ?
C9 H2 0.9800 . ?
C9 H5 0.9800 . ?
C9 H4 0.9800 . ?
C10 H3 0.9800 . ?
C10 H22 0.9800 . ?
C10 H21 0.9800 . ?
C11 C14 1.393(2) . ?
C12 H7 0.9800 . ?
C12 H6 0.9800 . ?
C12 H8 0.9800 . ?
C13 C14 1.3829(19) . ?
C13 C15 1.4667(19) . ?
C14 H9 0.9500 . ?
C15 C16 1.3895(19) . ?
C16 C17 1.389(2) . ?
C16 H20 0.9500 . ?
C18 H10 0.9800 . ?
C18 H11 0.9800 . ?
C18 H12 0.9800 . ?
C19 H19 0.9500 . ?
C20 H16 0.9800 . ?
C20 H17 0.9800 . ?
C20 H18 0.9800 . ?
C21 H26 0.9800 . ?
C21 H27 0.9800 . ?
C21 H23 0.9800 . ?
C22 C23 1.3958(19) . ?
C22 C31 1.4088(19) . ?
C23 C24 1.3842(19) . ?
C23 H42 0.9500 . ?
C24 C36 1.4013(18) . ?
C24 C25 1.4652(19) . ?
C25 C34 1.3897(19) . ?
C25 C26 1.3998(19) . ?
C26 C27 1.392(2) . ?
C26 C35 1.4811(18) . ?
C27 C28 1.3864(19) . ?
C27 H34 0.9500 . ?
C28 C32 1.4149(19) . ?
C29 H28 0.9800 . ?
C29 H24 0.9800 . ?
C29 H29 0.9800 . ?
C30 H43 0.9800 . ?
C30 H25 0.9800 . ?
C30 H44 0.9800 . ?
C31 C37 1.399(2) . ?
C32 C34 1.385(2) . ?
C33 H30 0.9800 . ?
C33 H32 0.9800 . ?
C33 H31 0.9800 . ?
C34 H33 0.9500 . ?
C35 C39 1.3481(19) . ?
C35 C36 1.4856(19) . ?
C36 C37 1.3988(19) . ?
C38 H35 0.9800 . ?
C38 H37 0.9800 . ?
C38 H36 0.9800 . ?
C39 H41 0.9500 . ?
C40 H40 0.9800 . ?
C40 H38 0.9800 . ?
C40 H39 0.9800 . ?
 
loop_
 _geom_angle_atom_site_label_1
 _geom_angle_atom_site_label_2
 _geom_angle_atom_site_label_3
 _geom_angle
 _geom_angle_site_symmetry_1
 _geom_angle_site_symmetry_3
 _geom_angle_publ_flag
O6 S1 O7 115.73(6) . . ?
O6 S1 C19 109.71(6) . . ?
O7 S1 C19 110.87(6) . . ?
O6 S1 C20 108.48(7) . . ?
O7 S1 C20 108.98(7) . . ?
C19 S1 C20 102.20(7) . . ?
O13 S2 O14 116.48(7) . . ?
O13 S2 C39 111.31(7) . . ?
O14 S2 C39 109.63(7) . . ?
O13 S2 C40 108.89(7) . . ?
O14 S2 C40 108.39(7) . . ?
C39 S2 C40 100.98(7) . . ?
C2 O1 C1 116.73(11) . . ?
C8 O2 C9 114.25(11) . . ?
C11 O3 C10 117.04(11) . . ?
C7 O4 C12 115.81(11) . . ?
C17 O5 C18 117.07(11) . . ?
C22 O8 C21 117.24(11) . . ?
C28 O9 C29 116.82(11) . . ?
C31 O10 C30 114.01(11) . . ?
C32 O11 C33 117.26(11) . . ?
C37 O12 C38 117.96(11) . . ?
O1 C1 H13 109.5 . . ?
O1 C1 H14 109.5 . . ?
H13 C1 H14 109.5 . . ?
O1 C1 H1 109.5 . . ?
H13 C1 H1 109.5 . . ?
H14 C1 H1 109.5 . . ?
O1 C2 C3 124.38(13) . . ?
O1 C2 C17 114.97(12) . . ?
C3 C2 C17 120.64(13) . . ?
C2 C3 C4 118.87(13) . . ?
C2 C3 H15 120.6 . . ?
C4 C3 H15 120.6 . . ?
C15 C4 C3 120.01(13) . . ?
C15 C4 C5 108.58(12) . . ?
C3 C4 C5 131.26(13) . . ?
C19 C5 C4 130.74(13) . . ?
C19 C5 C6 123.91(13) . . ?
C4 C5 C6 105.21(11) . . ?
C7 C6 C13 119.64(12) . . ?
C7 C6 C5 131.35(12) . . ?
C13 C6 C5 108.85(12) . . ?
O4 C7 C6 119.34(12) . . ?
O4 C7 C8 121.61(12) . . ?
C6 C7 C8 118.92(12) . . ?
O2 C8 C7 120.06(12) . . ?
O2 C8 C11 119.54(12) . . ?
C7 C8 C11 120.34(13) . . ?
O2 C9 H2 109.5 . . ?
O2 C9 H5 109.5 . . ?
H2 C9 H5 109.5 . . ?
O2 C9 H4 109.5 . . ?
H2 C9 H4 109.5 . . ?
H5 C9 H4 109.5 . . ?
O3 C10 H3 109.5 . . ?
O3 C10 H22 109.5 . . ?
H3 C10 H22 109.5 . . ?
O3 C10 H21 109.5 . . ?
H3 C10 H21 109.5 . . ?
H22 C10 H21 109.5 . . ?
O3 C11 C14 124.66(12) . . ?
O3 C11 C8 114.58(12) . . ?
C14 C11 C8 120.76(13) . . ?
O4 C12 H7 109.5 . . ?
O4 C12 H6 109.5 . . ?
H7 C12 H6 109.5 . . ?
O4 C12 H8 109.5 . . ?
H7 C12 H8 109.5 . . ?
H6 C12 H8 109.5 . . ?
C14 C13 C6 122.24(13) . . ?
C14 C13 C15 129.70(12) . . ?
C6 C13 C15 108.06(12) . . ?
C13 C14 C11 118.03(13) . . ?
C13 C14 H9 121.0 . . ?
C11 C14 H9 121.0 . . ?
C16 C15 C4 121.63(13) . . ?
C16 C15 C13 129.29(13) . . ?
C4 C15 C13 109.00(12) . . ?
C17 C16 C15 118.19(13) . . ?
C17 C16 H20 120.9 . . ?
C15 C16 H20 120.9 . . ?
O5 C17 C16 124.35(13) . . ?
O5 C17 C2 115.02(12) . . ?
C16 C17 C2 120.62(12) . . ?
O5 C18 H10 109.5 . . ?
O5 C18 H11 109.5 . . ?
H10 C18 H11 109.5 . . ?
O5 C18 H12 109.5 . . ?
H10 C18 H12 109.5 . . ?
H11 C18 H12 109.5 . . ?
C5 C19 S1 126.33(11) . . ?
C5 C19 H19 116.8 . . ?
S1 C19 H19 116.8 . . ?
S1 C20 H16 109.5 . . ?
S1 C20 H17 109.5 . . ?
H16 C20 H17 109.5 . . ?
S1 C20 H18 109.5 . . ?
H16 C20 H18 109.5 . . ?
H17 C20 H18 109.5 . . ?
O8 C21 H26 109.5 . . ?
O8 C21 H27 109.5 . . ?
H26 C21 H27 109.5 . . ?
O8 C21 H23 109.5 . . ?
H26 C21 H23 109.5 . . ?
H27 C21 H23 109.5 . . ?
O8 C22 C23 124.19(12) . . ?
O8 C22 C31 114.78(12) . . ?
C23 C22 C31 121.03(13) . . ?
C24 C23 C22 117.84(12) . . ?
C24 C23 H42 121.1 . . ?
C22 C23 H42 121.1 . . ?
C23 C24 C36 122.32(13) . . ?
C23 C24 C25 129.48(12) . . ?
C36 C24 C25 108.07(12) . . ?
C34 C25 C26 121.39(13) . . ?
C34 C25 C24 129.44(13) . . ?
C26 C25 C24 109.17(12) . . ?
C27 C26 C25 120.08(12) . . ?
C27 C26 C35 131.54(13) . . ?
C25 C26 C35 108.38(12) . . ?
C28 C27 C26 119.01(13) . . ?
C28 C27 H34 120.5 . . ?
C26 C27 H34 120.5 . . ?
O9 C28 C27 124.63(13) . . ?
O9 C28 C32 114.81(12) . . ?
C27 C28 C32 120.56(13) . . ?
O9 C29 H28 109.5 . . ?
O9 C29 H24 109.5 . . ?
H28 C29 H24 109.5 . . ?
O9 C29 H29 109.5 . . ?
H28 C29 H29 109.5 . . ?
H24 C29 H29 109.5 . . ?
O10 C30 H43 109.5 . . ?
O10 C30 H25 109.5 . . ?
H43 C30 H25 109.5 . . ?
O10 C30 H44 109.5 . . ?
H43 C30 H44 109.5 . . ?
H25 C30 H44 109.5 . . ?
O10 C31 C37 120.61(12) . . ?
O10 C31 C22 119.15(12) . . ?
C37 C31 C22 120.19(12) . . ?
O11 C32 C34 124.51(12) . . ?
O11 C32 C28 115.07(12) . . ?
C34 C32 C28 120.43(12) . . ?
O11 C33 H30 109.5 . . ?
O11 C33 H32 109.5 . . ?
H30 C33 H32 109.5 . . ?
O11 C33 H31 109.5 . . ?
H30 C33 H31 109.5 . . ?
H32 C33 H31 109.5 . . ?
C32 C34 C25 118.53(13) . . ?
C32 C34 H33 120.7 . . ?
C25 C34 H33 120.7 . . ?
C39 C35 C26 130.61(13) . . ?
C39 C35 C36 123.75(13) . . ?
C26 C35 C36 105.42(11) . . ?
C37 C36 C24 119.57(13) . . ?
C37 C36 C35 131.12(12) . . ?
C24 C36 C35 108.81(12) . . ?
O12 C37 C36 118.09(12) . . ?
O12 C37 C31 122.80(12) . . ?
C36 C37 C31 119.01(12) . . ?
O12 C38 H35 109.5 . . ?
O12 C38 H37 109.5 . . ?
H35 C38 H37 109.5 . . ?
O12 C38 H36 109.5 . . ?
H35 C38 H36 109.5 . . ?
H37 C38 H36 109.5 . . ?
C35 C39 S2 127.00(11) . . ?
C35 C39 H41 116.5 . . ?
S2 C39 H41 116.5 . . ?
S2 C40 H40 109.5 . . ?
S2 C40 H38 109.5 . . ?
H40 C40 H38 109.5 . . ?
S2 C40 H39 109.5 . . ?
H40 C40 H39 109.5 . . ?
H38 C40 H39 109.5 . . ?
 
_refine_diff_density_max    0.368
_refine_diff_density_min   -0.446
_refine_diff_density_rms    0.048

_shelxl_version_number 2014/6



 
data_181023lt_0m
 
_audit_creation_method            SHELXL-2014/6
_chemical_name_systematic         ?
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C15 H14 O4 S2' 
_chemical_formula_weight          322.38

loop_
 _atom_type_symbol
 _atom_type_description
 _atom_type_scat_dispersion_real
 _atom_type_scat_dispersion_imag
 _atom_type_scat_source
 'C'  'C'   0.0033   0.0016
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'H'  'H'   0.0000   0.0000
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'O'  'O'   0.0106   0.0060
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'S'  'S'   0.1246   0.1234
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 
_space_group_crystal_system       triclinic
_space_group_IT_number            2
_space_group_name_H-M_alt         'P -1'
_space_group_name_Hall            '-P 1'
 
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
 
loop_
 _space_group_symop_operation_xyz
 'x, y, z'
 '-x, -y, -z'
 
_cell_length_a                    8.6178(7)
_cell_length_b                    9.0183(7)
_cell_length_c                    9.6399(8)
_cell_angle_alpha                 79.873(4)
_cell_angle_beta                  75.377(4)
_cell_angle_gamma                 85.646(4)
_cell_volume                      713.24(10)
_cell_formula_units_Z             2
_cell_measurement_temperature     100(2)
_cell_measurement_reflns_used     6181
_cell_measurement_theta_min       2.2128
_cell_measurement_theta_max       26.3624
 
_exptl_crystal_description        tabullar
_exptl_crystal_colour             red
_exptl_crystal_density_meas       'not measured'
_exptl_crystal_density_method     'not measured'
_exptl_crystal_density_diffrn     1.501          
_exptl_crystal_F_000              336
_exptl_transmission_factor_min    ?
_exptl_transmission_factor_max    ?
_exptl_crystal_size_max           0.20
_exptl_crystal_size_mid           0.19
_exptl_crystal_size_min           0.08
_exptl_absorpt_coefficient_mu     0.386
_shelx_estimated_absorpt_T_min    ?
_shelx_estimated_absorpt_T_max    ?
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.6515  
_exptl_absorpt_correction_T_max   0.7454
_exptl_absorpt_process_details    'SADABS V2014/4 (Bruker AXS Inc.)'
_exptl_absorpt_special_details    ?
_diffrn_ambient_temperature       100(2)
_diffrn_radiation_wavelength      0.71073
_diffrn_radiation_type            MoK\a
_diffrn_source                    ?
_diffrn_measurement_device_type   'Bruker APEX-II CCD'
_diffrn_measurement_method        'φ and ω scans'
_diffrn_detector_area_resol_mean  8.3333
_diffrn_reflns_number             9509
_diffrn_reflns_av_unetI/netI      0.0262
_diffrn_reflns_av_R_equivalents   0.0244
_diffrn_reflns_limit_h_min        -10
_diffrn_reflns_limit_h_max        10
_diffrn_reflns_limit_k_min        -11
_diffrn_reflns_limit_k_max        10
_diffrn_reflns_limit_l_min        -11
_diffrn_reflns_limit_l_max        12
_diffrn_reflns_theta_min          2.213
_diffrn_reflns_theta_max          26.392
_diffrn_reflns_theta_full         25.242
_diffrn_measured_fraction_theta_max   0.959
_diffrn_measured_fraction_theta_full  0.968
_diffrn_reflns_Laue_measured_fraction_max    0.959
_diffrn_reflns_Laue_measured_fraction_full   0.968
_diffrn_reflns_point_group_measured_fraction_max   0.959
_diffrn_reflns_point_group_measured_fraction_full  0.968
_reflns_number_total              2792
_reflns_number_gt                 2524
_reflns_threshold_expression      'I > 2σ(I)'
_reflns_Friedel_coverage          0.000
_reflns_Friedel_fraction_max      .
_reflns_Friedel_fraction_full     .
 
_reflns_special_details
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
 
_computing_data_collection        'Bruker APEX2'
_computing_cell_refinement        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction         'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution     ?
_computing_structure_refinement   'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics     'Bruker SHELXTL'
_computing_publication_material   'Bruker SHELXTL'
_refine_special_details           ?
_refine_ls_structure_factor_coef  Fsqd
_refine_ls_matrix_type            full
_refine_ls_weighting_scheme       calc
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0362P)²+0.5505P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary      ?
_atom_sites_solution_secondary    ?
_atom_sites_solution_hydrogens    geom
_refine_ls_hydrogen_treatment     constr
_refine_ls_extinction_method      none
_refine_ls_extinction_coef        .
_refine_ls_number_reflns          2792
_refine_ls_number_parameters      193
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0360
_refine_ls_R_factor_gt            0.0321
_refine_ls_wR_factor_ref          0.0824
_refine_ls_wR_factor_gt           0.0793
_refine_ls_goodness_of_fit_ref    1.040
_refine_ls_restrained_S_all       1.040
_refine_ls_shift/su_max           0.001
_refine_ls_shift/su_mean          0.000
 
loop_
 _atom_site_label
 _atom_site_type_symbol
 _atom_site_fract_x
 _atom_site_fract_y
 _atom_site_fract_z
 _atom_site_U_iso_or_equiv
 _atom_site_adp_type
 _atom_site_occupancy
 _atom_site_site_symmetry_order  
 _atom_site_calc_flag
 _atom_site_refinement_flags_posn
 _atom_site_refinement_flags_adp
 _atom_site_refinement_flags_occupancy
 _atom_site_disorder_assembly
 _atom_site_disorder_group
S1 S 0.45150(4) 0.80721(5) 0.74390(4) 0.01511(12) Uani 1 1 d . . . . .
S2 S 0.70466(5) 0.51021(5) 0.89291(4) 0.01773(12) Uani 1 1 d . . . . .
O1 O 1.39269(13) 0.79844(14) 0.26497(13) 0.0214(3) Uani 1 1 d . . . . .
O2 O 1.17393(14) 0.97522(14) 0.18088(13) 0.0210(3) Uani 1 1 d . . . . .
O3 O 0.34152(14) 0.91276(15) 0.68415(13) 0.0244(3) Uani 1 1 d . . . . .
O4 O 0.41163(14) 0.65004(14) 0.78003(13) 0.0208(3) Uani 1 1 d . . . . .
C1 C 1.5196(2) 0.7032(2) 0.3056(2) 0.0244(4) Uani 1 1 d . . . . .
H5 H 1.5230 0.7125 0.4046 0.037 Uiso 1 1 calc R U . . .
H1 H 1.6220 0.7334 0.2383 0.037 Uiso 1 1 calc R U . . .
H4 H 1.5007 0.5983 0.3019 0.037 Uiso 1 1 calc R U . . .
C2 C 1.24107(19) 0.7777(2) 0.35317(18) 0.0172(4) Uani 1 1 d . . . . .
C3 C 1.20283(19) 0.6709(2) 0.47812(18) 0.0174(4) Uani 1 1 d . . . . .
H10 H 1.2829 0.6035 0.5078 0.021 Uiso 1 1 calc R U . . .
C4 C 1.04367(19) 0.6651(2) 0.55896(18) 0.0158(3) Uani 1 1 d . . . . .
C5 C 0.92663(19) 0.7653(2) 0.51525(17) 0.0153(3) Uani 1 1 d . . . . .
C6 C 0.76936(19) 0.73921(19) 0.62429(17) 0.0152(3) Uani 1 1 d . . . . .
C7 C 0.63792(19) 0.8279(2) 0.61840(17) 0.0158(3) Uani 1 1 d . . . . .
H13 H 0.6469 0.9088 0.5393 0.019 Uiso 1 1 calc R U . . .
C8 C 0.4762(2) 0.8667(2) 0.90099(18) 0.0204(4) Uani 1 1 d . . . . .
H2 H 0.3722 0.8689 0.9714 0.031 Uiso 1 1 calc R U . . .
H3 H 0.5199 0.9678 0.8753 0.031 Uiso 1 1 calc R U . . .
H14 H 0.5505 0.7965 0.9438 0.031 Uiso 1 1 calc R U . . .
C9 C 1.1217(2) 0.8770(2) 0.30806(17) 0.0168(3) Uani 1 1 d . . . . .
C10 C 1.0597(2) 1.0862(2) 0.14022(19) 0.0208(4) Uani 1 1 d . . . . .
H8 H 0.9712 1.0366 0.1221 0.031 Uiso 1 1 calc R U . . .
H6 H 1.1115 1.1534 0.0517 0.031 Uiso 1 1 calc R U . . .
H7 H 1.0180 1.1451 0.2188 0.031 Uiso 1 1 calc R U . . .
C11 C 0.96342(19) 0.8723(2) 0.39011(18) 0.0167(3) Uani 1 1 d . . . . .
H9 H 0.8832 0.9402 0.3614 0.020 Uiso 1 1 calc R U . . .
C12 C 0.96532(19) 0.5693(2) 0.69500(18) 0.0164(3) Uani 1 1 d . . . . .
C13 C 1.0090(2) 0.4547(2) 0.79961(19) 0.0199(4) Uani 1 1 d . . . . .
H12 H 1.1144 0.4121 0.7925 0.024 Uiso 1 1 calc R U . . .
C14 C 0.8796(2) 0.4126(2) 0.9129(2) 0.0216(4) Uani 1 1 d . . . . .
H11 H 0.8858 0.3375 0.9940 0.026 Uiso 1 1 calc R U . . .
C15 C 0.80371(19) 0.61148(19) 0.73069(17) 0.0156(3) Uani 1 1 d . . . . .
 
 
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
 
loop_
 _geom_bond_atom_site_label_1
 _geom_bond_atom_site_label_2
 _geom_bond_distance
 _geom_bond_site_symmetry_2
 _geom_bond_publ_flag
S1 O3 1.4429(13) . ?
S1 O4 1.4451(13) . ?
S1 C7 1.7505(16) . ?
S1 C8 1.7584(18) . ?
S2 C15 1.7176(17) . ?
S2 C14 1.7234(18) . ?
O1 C2 1.3731(19) . ?
O1 C1 1.429(2) . ?
O2 C9 1.375(2) . ?
O2 C10 1.425(2) . ?
C1 H5 0.9800 . ?
C1 H1 0.9800 . ?
C1 H4 0.9800 . ?
C2 C3 1.388(2) . ?
C2 C9 1.413(2) . ?
C3 C4 1.396(2) . ?
C3 H10 0.9500 . ?
C4 C5 1.398(2) . ?
C4 C12 1.471(2) . ?
C5 C11 1.390(2) . ?
C5 C6 1.496(2) . ?
C6 C7 1.344(2) . ?
C6 C15 1.467(2) . ?
C7 H13 0.9500 . ?
C8 H2 0.9800 . ?
C8 H3 0.9800 . ?
C8 H14 0.9800 . ?
C9 C11 1.393(2) . ?
C10 H8 0.9800 . ?
C10 H6 0.9800 . ?
C10 H7 0.9800 . ?
C11 H9 0.9500 . ?
C12 C15 1.388(2) . ?
C12 C13 1.412(2) . ?
C13 C14 1.372(2) . ?
C13 H12 0.9500 . ?
C14 H11 0.9500 . ?
 
loop_
 _geom_angle_atom_site_label_1
 _geom_angle_atom_site_label_2
 _geom_angle_atom_site_label_3
 _geom_angle
 _geom_angle_site_symmetry_1
 _geom_angle_site_symmetry_3
 _geom_angle_publ_flag
O3 S1 O4 117.99(8) . . ?
O3 S1 C7 106.35(8) . . ?
O4 S1 C7 109.79(8) . . ?
O3 S1 C8 107.93(9) . . ?
O4 S1 C8 108.35(8) . . ?
C7 S1 C8 105.76(8) . . ?
C15 S2 C14 90.99(8) . . ?
C2 O1 C1 117.33(13) . . ?
C9 O2 C10 116.55(12) . . ?
O1 C1 H5 109.5 . . ?
O1 C1 H1 109.5 . . ?
H5 C1 H1 109.5 . . ?
O1 C1 H4 109.5 . . ?
H5 C1 H4 109.5 . . ?
H1 C1 H4 109.5 . . ?
O1 C2 C3 124.64(15) . . ?
O1 C2 C9 114.45(14) . . ?
C3 C2 C9 120.90(14) . . ?
C2 C3 C4 118.27(15) . . ?
C2 C3 H10 120.9 . . ?
C4 C3 H10 120.9 . . ?
C3 C4 C5 120.58(15) . . ?
C3 C4 C12 131.80(16) . . ?
C5 C4 C12 107.61(14) . . ?
C11 C5 C4 121.64(15) . . ?
C11 C5 C6 128.86(15) . . ?
C4 C5 C6 109.47(14) . . ?
C7 C6 C15 132.82(15) . . ?
C7 C6 C5 122.97(15) . . ?
C15 C6 C5 104.07(14) . . ?
C6 C7 S1 125.61(13) . . ?
C6 C7 H13 117.2 . . ?
S1 C7 H13 117.2 . . ?
S1 C8 H2 109.5 . . ?
S1 C8 H3 109.5 . . ?
H2 C8 H3 109.5 . . ?
S1 C8 H14 109.5 . . ?
H2 C8 H14 109.5 . . ?
H3 C8 H14 109.5 . . ?
O2 C9 C11 123.94(15) . . ?
O2 C9 C2 115.38(14) . . ?
C11 C9 C2 120.68(15) . . ?
O2 C10 H8 109.5 . . ?
O2 C10 H6 109.5 . . ?
H8 C10 H6 109.5 . . ?
O2 C10 H7 109.5 . . ?
H8 C10 H7 109.5 . . ?
H6 C10 H7 109.5 . . ?
C5 C11 C9 117.90(15) . . ?
C5 C11 H9 121.0 . . ?
C9 C11 H9 121.0 . . ?
C15 C12 C13 113.05(15) . . ?
C15 C12 C4 108.59(15) . . ?
C13 C12 C4 138.28(15) . . ?
C14 C13 C12 111.32(15) . . ?
C14 C13 H12 124.3 . . ?
C12 C13 H12 124.3 . . ?
C13 C14 S2 113.06(13) . . ?
C13 C14 H11 123.5 . . ?
S2 C14 H11 123.5 . . ?
C12 C15 C6 110.20(14) . . ?
C12 C15 S2 111.58(13) . . ?
C6 C15 S2 137.97(13) . . ?
 
_refine_diff_density_max    0.531
_refine_diff_density_min   -0.323
_refine_diff_density_rms    0.056

_shelxl_version_number 2014/6



 
data_mo_181107lt_0m
 
_audit_creation_method            SHELXL-2014/6
_chemical_name_systematic         ?
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C32 H32 O4' 
_chemical_formula_weight          480.57

loop_
 _atom_type_symbol
 _atom_type_description
 _atom_type_scat_dispersion_real
 _atom_type_scat_dispersion_imag
 _atom_type_scat_source
 'C'  'C'   0.0033   0.0016
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'H'  'H'   0.0000   0.0000
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'O'  'O'   0.0106   0.0060
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 
_space_group_crystal_system       triclinic
_space_group_IT_number            2
_space_group_name_H-M_alt         'P -1'
_space_group_name_Hall            '-P 1'
 
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
 
loop_
 _space_group_symop_operation_xyz
 'x, y, z'
 '-x, -y, -z'
 
_cell_length_a                    10.592(4)
_cell_length_b                    10.873(5)
_cell_length_c                    11.134(4)
_cell_angle_alpha                 100.081(13)
_cell_angle_beta                  94.108(13)
_cell_angle_gamma                 96.439(12)
_cell_volume                      1249.1(9)
_cell_formula_units_Z             2
_cell_measurement_temperature     99(2)
_cell_measurement_reflns_used     5664
_cell_measurement_theta_min       2.5515
_cell_measurement_theta_max       26.2578
 
_exptl_crystal_description        tabullar
_exptl_crystal_colour             colorless
_exptl_crystal_density_meas       'not measured'
_exptl_crystal_density_method     'not measured'
_exptl_crystal_density_diffrn     1.278          
_exptl_crystal_F_000              512
_exptl_transmission_factor_min    ?
_exptl_transmission_factor_max    ?
_exptl_crystal_size_max           0.15
_exptl_crystal_size_mid           0.15
_exptl_crystal_size_min           0.05
_exptl_absorpt_coefficient_mu     0.083
_shelx_estimated_absorpt_T_min    ?
_shelx_estimated_absorpt_T_max    ?
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.5434  
_exptl_absorpt_correction_T_max   0.7454
_exptl_absorpt_process_details    'SADABS V2014/4 (Bruker AXS Inc.)'
_exptl_absorpt_special_details    ?
_diffrn_ambient_temperature       99(2)
_diffrn_radiation_wavelength      0.71073
_diffrn_radiation_type            MoK\a
_diffrn_source                    ?
_diffrn_measurement_device_type   'Bruker APEX-II CCD'
_diffrn_measurement_method        'φ and ω scans'
_diffrn_detector_area_resol_mean  8.3333
_diffrn_reflns_number             29295
_diffrn_reflns_av_unetI/netI      0.0600
_diffrn_reflns_av_R_equivalents   0.0764
_diffrn_reflns_limit_h_min        -13
_diffrn_reflns_limit_h_max        13
_diffrn_reflns_limit_k_min        -13
_diffrn_reflns_limit_k_max        13
_diffrn_reflns_limit_l_min        -13
_diffrn_reflns_limit_l_max        13
_diffrn_reflns_theta_min          1.866
_diffrn_reflns_theta_max          26.602
_diffrn_reflns_theta_full         25.242
_diffrn_measured_fraction_theta_max   0.983
_diffrn_measured_fraction_theta_full  0.996
_diffrn_reflns_Laue_measured_fraction_max    0.983
_diffrn_reflns_Laue_measured_fraction_full   0.996
_diffrn_reflns_point_group_measured_fraction_max   0.983
_diffrn_reflns_point_group_measured_fraction_full  0.996
_reflns_number_total              5145
_reflns_number_gt                 3540
_reflns_threshold_expression      'I > 2σ(I)'
_reflns_Friedel_coverage          0.000
_reflns_Friedel_fraction_max      .
_reflns_Friedel_fraction_full     .
 
_reflns_special_details
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
 
_computing_data_collection        'Bruker APEX2'
_computing_cell_refinement        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction         'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution     ?
_computing_structure_refinement   'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics     'Bruker SHELXTL'
_computing_publication_material   'Bruker SHELXTL'
_refine_special_details           ?
_refine_ls_structure_factor_coef  Fsqd
_refine_ls_matrix_type            full
_refine_ls_weighting_scheme       calc
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1286P)²+1.5710P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary      ?
_atom_sites_solution_secondary    ?
_atom_sites_solution_hydrogens    geom
_refine_ls_hydrogen_treatment     constr
_refine_ls_extinction_method      none
_refine_ls_extinction_coef        .
_refine_ls_number_reflns          5145
_refine_ls_number_parameters      331
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.1193
_refine_ls_R_factor_gt            0.0837
_refine_ls_wR_factor_ref          0.2436
_refine_ls_wR_factor_gt           0.2196
_refine_ls_goodness_of_fit_ref    1.065
_refine_ls_restrained_S_all       1.065
_refine_ls_shift/su_max           0.008
_refine_ls_shift/su_mean          0.001
 
loop_
 _atom_site_label
 _atom_site_type_symbol
 _atom_site_fract_x
 _atom_site_fract_y
 _atom_site_fract_z
 _atom_site_U_iso_or_equiv
 _atom_site_adp_type
 _atom_site_occupancy
 _atom_site_site_symmetry_order  
 _atom_site_calc_flag
 _atom_site_refinement_flags_posn
 _atom_site_refinement_flags_adp
 _atom_site_refinement_flags_occupancy
 _atom_site_disorder_assembly
 _atom_site_disorder_group
O1 O 0.2763(2) 0.3428(2) 0.1133(2) 0.0208(5) Uani 1 1 d . . . . .
O2 O 0.1996(2) 0.1077(2) 0.0893(2) 0.0244(6) Uani 1 1 d . . . . .
O3 O 0.1402(2) 0.6717(2) -0.0010(2) 0.0222(5) Uani 1 1 d . . . . .
O4 O 0.3777(2) 0.7459(2) 0.0621(2) 0.0245(6) Uani 1 1 d . . . . .
C1 C 0.3220(3) 0.4722(3) 0.1206(3) 0.0252(8) Uani 1 1 d . . . . .
H16 H 0.2583 0.5241 0.1540 0.038 Uiso 1 1 calc R U . . .
H3 H 0.3375 0.4880 0.0386 0.038 Uiso 1 1 calc R U . . .
H1 H 0.4018 0.4937 0.1743 0.038 Uiso 1 1 calc R U . . .
C2 C 0.2521(3) 0.3033(3) 0.2211(3) 0.0181(7) Uani 1 1 d . . . . .
C3 C 0.2652(3) 0.3804(3) 0.3359(3) 0.0198(7) Uani 1 1 d . . . . .
H7 H 0.2903 0.4684 0.3450 0.024 Uiso 1 1 calc R U . . .
C4 C 0.2406(3) 0.3258(3) 0.4379(3) 0.0200(7) Uani 1 1 d . . . . .
C5 C 0.2531(3) 0.3883(3) 0.5717(3) 0.0206(7) Uani 1 1 d . . . . .
H8 H 0.1890 0.4490 0.5852 0.025 Uiso 1 1 calc R U . . .
C6 C 0.2171(3) 0.2776(3) 0.6339(3) 0.0198(7) Uani 1 1 d . . . . .
C7 C 0.2126(3) 0.2751(3) 0.7563(3) 0.0222(7) Uani 1 1 d . . . . .
H12 H 0.2326 0.3504 0.8155 0.027 Uiso 1 1 calc R U . . .
C8 C 0.1783(3) 0.1604(3) 0.7928(3) 0.0260(8) Uani 1 1 d . . . . .
H2 H 0.1747 0.1576 0.8773 0.031 Uiso 1 1 calc R U . . .
C9 C 0.2103(3) 0.1736(3) 0.2073(3) 0.0186(7) Uani 1 1 d . . . . .
C10 C 0.1609(4) -0.0241(3) 0.0709(3) 0.0289(8) Uani 1 1 d . . . . .
H5 H 0.2211 -0.0631 0.1186 0.043 Uiso 1 1 calc R U . . .
H4 H 0.1596 -0.0604 -0.0163 0.043 Uiso 1 1 calc R U . . .
H6 H 0.0753 -0.0397 0.0976 0.043 Uiso 1 1 calc R U . . .
C11 C 0.1848(3) 0.1197(3) 0.3084(3) 0.0186(7) Uani 1 1 d . . . . .
H15 H 0.1567 0.0322 0.2994 0.022 Uiso 1 1 calc R U . . .
C12 C 0.2017(3) 0.1976(3) 0.4240(3) 0.0184(7) Uani 1 1 d . . . . .
C13 C 0.1873(3) 0.1659(3) 0.5446(3) 0.0199(7) Uani 1 1 d . . . . .
C14 C 0.1532(3) 0.0514(3) 0.5822(3) 0.0227(7) Uani 1 1 d . . . . .
H14 H 0.1331 -0.0243 0.5236 0.027 Uiso 1 1 calc R U . . .
C15 C 0.1492(3) 0.0501(3) 0.7059(3) 0.0249(8) Uani 1 1 d . . . . .
H13 H 0.1262 -0.0274 0.7319 0.030 Uiso 1 1 calc R U . . .
C16 C 0.3870(3) 0.4569(3) 0.6177(3) 0.0244(8) Uani 1 1 d . . . . .
H11 H 0.3895 0.4929 0.7051 0.037 Uiso 1 1 calc R U . . .
H10 H 0.4073 0.5244 0.5717 0.037 Uiso 1 1 calc R U . . .
H9 H 0.4497 0.3971 0.6058 0.037 Uiso 1 1 calc R U . . .
C17 C 0.0047(3) 0.6536(3) -0.0273(3) 0.0250(8) Uani 1 1 d . . . . .
H20 H -0.0226 0.7265 -0.0578 0.037 Uiso 1 1 calc R U . . .
H17 H -0.0359 0.6443 0.0476 0.037 Uiso 1 1 calc R U . . .
H21 H -0.0205 0.5775 -0.0896 0.037 Uiso 1 1 calc R U . . .
C18 C 0.2094(3) 0.6996(3) -0.0946(3) 0.0183(7) Uani 1 1 d . . . . .
C19 C 0.1606(3) 0.6915(3) -0.2142(3) 0.0199(7) Uani 1 1 d . . . . .
H22 H 0.0729 0.6631 -0.2383 0.024 Uiso 1 1 calc R U . . .
C20 C 0.2423(3) 0.7256(3) -0.2999(3) 0.0205(7) Uani 1 1 d . . . . .
C21 C 0.2180(3) 0.7238(3) -0.4306(3) 0.0218(7) Uani 1 1 d . . . . .
C22 C 0.1070(3) 0.6893(3) -0.5099(3) 0.0261(8) Uani 1 1 d . . . . .
H23 H 0.0292 0.6595 -0.4809 0.031 Uiso 1 1 calc R U . . .
C23 C 0.1120(3) 0.6993(4) -0.6321(3) 0.0304(8) Uani 1 1 d . . . . .
H25 H 0.0369 0.6765 -0.6870 0.037 Uiso 1 1 calc R U . . .
C24 C 0.2262(4) 0.7424(3) -0.6751(3) 0.0295(8) Uani 1 1 d . . . . .
H18 H 0.2282 0.7493 -0.7588 0.035 Uiso 1 1 calc R U . . .
C25 C 0.5104(3) 0.7830(4) 0.1003(4) 0.0318(9) Uani 1 1 d . . . . .
H19 H 0.5611 0.7286 0.0490 0.048 Uiso 1 1 calc R U . . .
H31 H 0.5274 0.7750 0.1861 0.048 Uiso 1 1 calc R U . . .
H32 H 0.5337 0.8707 0.0920 0.048 Uiso 1 1 calc R U . . .
C26 C 0.3405(3) 0.7411(3) -0.0587(3) 0.0202(7) Uani 1 1 d . . . . .
C27 C 0.3708(3) 0.7673(3) -0.2632(3) 0.0231(7) Uani 1 1 d . . . . .
C28 C 0.4400(3) 0.8000(3) -0.3701(3) 0.0251(8) Uani 1 1 d . . . . .
H26 H 0.5081 0.7442 -0.3869 0.030 Uiso 1 1 calc R U . . .
C29 C 0.3334(3) 0.7667(3) -0.4740(3) 0.0240(7) Uani 1 1 d . . . . .
C30 C 0.3373(3) 0.7754(3) -0.5957(3) 0.0272(8) Uani 1 1 d . . . . .
H24 H 0.4152 0.8038 -0.6252 0.033 Uiso 1 1 calc R U . . .
C31 C 0.4979(3) 0.9376(3) -0.3498(4) 0.0301(8) Uani 1 1 d . . . . .
H28 H 0.4299 0.9916 -0.3408 0.045 Uiso 1 1 calc R U . . .
H27 H 0.5441 0.9525 -0.4201 0.045 Uiso 1 1 calc R U . . .
H29 H 0.5572 0.9570 -0.2753 0.045 Uiso 1 1 calc R U . . .
C32 C 0.4201(3) 0.7756(3) -0.1433(3) 0.0244(8) Uani 1 1 d . . . . .
H30 H 0.5077 0.8046 -0.1193 0.029 Uiso 1 1 calc R U . . .
 
 
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
 
loop_
 _geom_bond_atom_site_label_1
 _geom_bond_atom_site_label_2
 _geom_bond_distance
 _geom_bond_site_symmetry_2
 _geom_bond_publ_flag
O1 C2 1.375(4) . ?
O1 C1 1.423(4) . ?
O2 C9 1.373(4) . ?
O2 C10 1.420(4) . ?
O3 C18 1.374(4) . ?
O3 C17 1.429(4) . ?
O4 C26 1.364(4) . ?
O4 C25 1.431(4) . ?
C1 H16 0.9800 . ?
C1 H3 0.9800 . ?
C1 H1 0.9800 . ?
C2 C3 1.389(5) . ?
C2 C9 1.408(5) . ?
C3 C4 1.398(5) . ?
C3 H7 0.9500 . ?
C4 C12 1.387(5) . ?
C4 C5 1.516(4) . ?
C5 C6 1.517(5) . ?
C5 C16 1.534(4) . ?
C5 H8 1.0000 . ?
C6 C7 1.372(5) . ?
C6 C13 1.418(5) . ?
C7 C8 1.396(5) . ?
C7 H12 0.9500 . ?
C8 C15 1.392(5) . ?
C8 H2 0.9500 . ?
C9 C11 1.386(5) . ?
C10 H5 0.9800 . ?
C10 H4 0.9800 . ?
C10 H6 0.9800 . ?
C11 C12 1.399(4) . ?
C11 H15 0.9500 . ?
C12 C13 1.458(5) . ?
C13 C14 1.399(5) . ?
C14 C15 1.383(5) . ?
C14 H14 0.9500 . ?
C15 H13 0.9500 . ?
C16 H11 0.9800 . ?
C16 H10 0.9800 . ?
C16 H9 0.9800 . ?
C17 H20 0.9800 . ?
C17 H17 0.9800 . ?
C17 H21 0.9800 . ?
C18 C19 1.377(5) . ?
C18 C26 1.417(4) . ?
C19 C20 1.402(5) . ?
C19 H22 0.9500 . ?
C20 C27 1.393(4) . ?
C20 C21 1.457(5) . ?
C21 C22 1.392(5) . ?
C21 C29 1.408(5) . ?
C22 C23 1.387(5) . ?
C22 H23 0.9500 . ?
C23 C24 1.395(5) . ?
C23 H25 0.9500 . ?
C24 C30 1.393(5) . ?
C24 H18 0.9500 . ?
C25 H19 0.9800 . ?
C25 H31 0.9800 . ?
C25 H32 0.9800 . ?
C26 C32 1.379(5) . ?
C27 C32 1.383(5) . ?
C27 C28 1.515(5) . ?
C28 C31 1.524(5) . ?
C28 C29 1.523(5) . ?
C28 H26 1.0000 . ?
C29 C30 1.377(5) . ?
C30 H24 0.9500 . ?
C31 H28 0.9800 . ?
C31 H27 0.9800 . ?
C31 H29 0.9800 . ?
C32 H30 0.9500 . ?
 
loop_
 _geom_angle_atom_site_label_1
 _geom_angle_atom_site_label_2
 _geom_angle_atom_site_label_3
 _geom_angle
 _geom_angle_site_symmetry_1
 _geom_angle_site_symmetry_3
 _geom_angle_publ_flag
C2 O1 C1 117.3(2) . . ?
C9 O2 C10 117.4(3) . . ?
C18 O3 C17 115.8(3) . . ?
C26 O4 C25 116.6(3) . . ?
O1 C1 H16 109.5 . . ?
O1 C1 H3 109.5 . . ?
H16 C1 H3 109.5 . . ?
O1 C1 H1 109.5 . . ?
H16 C1 H1 109.5 . . ?
H3 C1 H1 109.5 . . ?
O1 C2 C3 125.2(3) . . ?
O1 C2 C9 114.2(3) . . ?
C3 C2 C9 120.6(3) . . ?
C2 C3 C4 118.6(3) . . ?
C2 C3 H7 120.7 . . ?
C4 C3 H7 120.7 . . ?
C12 C4 C3 120.5(3) . . ?
C12 C4 C5 111.0(3) . . ?
C3 C4 C5 128.5(3) . . ?
C6 C5 C4 101.9(3) . . ?
C6 C5 C16 112.7(3) . . ?
C4 C5 C16 113.5(3) . . ?
C6 C5 H8 109.5 . . ?
C4 C5 H8 109.5 . . ?
C16 C5 H8 109.5 . . ?
C7 C6 C13 121.0(3) . . ?
C7 C6 C5 129.3(3) . . ?
C13 C6 C5 109.8(3) . . ?
C6 C7 C8 119.2(3) . . ?
C6 C7 H12 120.4 . . ?
C8 C7 H12 120.4 . . ?
C15 C8 C7 120.2(3) . . ?
C15 C8 H2 119.9 . . ?
C7 C8 H2 119.9 . . ?
O2 C9 C11 124.1(3) . . ?
O2 C9 C2 115.2(3) . . ?
C11 C9 C2 120.7(3) . . ?
O2 C10 H5 109.5 . . ?
O2 C10 H4 109.5 . . ?
H5 C10 H4 109.5 . . ?
O2 C10 H6 109.5 . . ?
H5 C10 H6 109.5 . . ?
H4 C10 H6 109.5 . . ?
C9 C11 C12 118.2(3) . . ?
C9 C11 H15 120.9 . . ?
C12 C11 H15 120.9 . . ?
C4 C12 C11 121.3(3) . . ?
C4 C12 C13 108.8(3) . . ?
C11 C12 C13 129.8(3) . . ?
C14 C13 C6 119.4(3) . . ?
C14 C13 C12 132.1(3) . . ?
C6 C13 C12 108.5(3) . . ?
C15 C14 C13 119.1(3) . . ?
C15 C14 H14 120.4 . . ?
C13 C14 H14 120.4 . . ?
C14 C15 C8 121.1(3) . . ?
C14 C15 H13 119.5 . . ?
C8 C15 H13 119.5 . . ?
C5 C16 H11 109.5 . . ?
C5 C16 H10 109.5 . . ?
H11 C16 H10 109.5 . . ?
C5 C16 H9 109.5 . . ?
H11 C16 H9 109.5 . . ?
H10 C16 H9 109.5 . . ?
O3 C17 H20 109.5 . . ?
O3 C17 H17 109.5 . . ?
H20 C17 H17 109.5 . . ?
O3 C17 H21 109.5 . . ?
H20 C17 H21 109.5 . . ?
H17 C17 H21 109.5 . . ?
O3 C18 C19 125.3(3) . . ?
O3 C18 C26 114.2(3) . . ?
C19 C18 C26 120.5(3) . . ?
C18 C19 C20 119.1(3) . . ?
C18 C19 H22 120.5 . . ?
C20 C19 H22 120.5 . . ?
C27 C20 C19 119.9(3) . . ?
C27 C20 C21 109.3(3) . . ?
C19 C20 C21 130.8(3) . . ?
C22 C21 C29 120.5(3) . . ?
C22 C21 C20 131.6(3) . . ?
C29 C21 C20 107.9(3) . . ?
C23 C22 C21 118.8(3) . . ?
C23 C22 H23 120.6 . . ?
C21 C22 H23 120.6 . . ?
C22 C23 C24 120.8(3) . . ?
C22 C23 H25 119.6 . . ?
C24 C23 H25 119.6 . . ?
C30 C24 C23 120.2(4) . . ?
C30 C24 H18 119.9 . . ?
C23 C24 H18 119.9 . . ?
O4 C25 H19 109.5 . . ?
O4 C25 H31 109.5 . . ?
H19 C25 H31 109.5 . . ?
O4 C25 H32 109.5 . . ?
H19 C25 H32 109.5 . . ?
H31 C25 H32 109.5 . . ?
O4 C26 C32 124.7(3) . . ?
O4 C26 C18 115.3(3) . . ?
C32 C26 C18 120.0(3) . . ?
C32 C27 C20 121.2(3) . . ?
C32 C27 C28 128.1(3) . . ?
C20 C27 C28 110.7(3) . . ?
C27 C28 C31 113.0(3) . . ?
C27 C28 C29 101.4(3) . . ?
C31 C28 C29 112.7(3) . . ?
C27 C28 H26 109.8 . . ?
C31 C28 H26 109.8 . . ?
C29 C28 H26 109.8 . . ?
C30 C29 C21 120.1(3) . . ?
C30 C29 C28 129.3(3) . . ?
C21 C29 C28 110.6(3) . . ?
C29 C30 C24 119.6(3) . . ?
C29 C30 H24 120.2 . . ?
C24 C30 H24 120.2 . . ?
C28 C31 H28 109.5 . . ?
C28 C31 H27 109.5 . . ?
H28 C31 H27 109.5 . . ?
C28 C31 H29 109.5 . . ?
H28 C31 H29 109.5 . . ?
H27 C31 H29 109.5 . . ?
C26 C32 C27 119.3(3) . . ?
C26 C32 H30 120.4 . . ?
C27 C32 H30 120.4 . . ?
 
_refine_diff_density_max    0.859
_refine_diff_density_min   -0.421
_refine_diff_density_rms    0.131

_shelxl_version_number 2014/6



 
data_181133LT
 
_audit_creation_method            SHELXL-2014/6
_chemical_name_systematic         ?
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C16 H15 F O2' 
_chemical_formula_weight          258.28

loop_
 _atom_type_symbol
 _atom_type_description
 _atom_type_scat_dispersion_real
 _atom_type_scat_dispersion_imag
 _atom_type_scat_source
 'C'  'C'   0.0033   0.0016
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'H'  'H'   0.0000   0.0000
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'O'  'O'   0.0106   0.0060
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'F'  'F'   0.0171   0.0103
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 
_space_group_crystal_system       monoclinic
_space_group_IT_number            14
_space_group_name_H-M_alt         'P 21/c'
_space_group_name_Hall            '-P 2ybc'
 
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
 
loop_
 _space_group_symop_operation_xyz
 'x, y, z'
 '-x, y+1/2, -z+1/2'
 '-x, -y, -z'
 'x, -y-1/2, z-1/2'
 
_cell_length_a                    11.0688(9)
_cell_length_b                    14.9195(13)
_cell_length_c                    7.8135(7)
_cell_angle_alpha                 90
_cell_angle_beta                  101.658(2)
_cell_angle_gamma                 90
_cell_volume                      1263.71(19)
_cell_formula_units_Z             4
_cell_measurement_temperature     100(2)
_cell_measurement_reflns_used     7530
_cell_measurement_theta_min       2.3223
_cell_measurement_theta_max       26.4553
 
_exptl_crystal_description        lump
_exptl_crystal_colour             colorless
_exptl_crystal_density_meas       'not measured'
_exptl_crystal_density_method     'not measured'
_exptl_crystal_density_diffrn     1.358          
_exptl_crystal_F_000              544
_exptl_transmission_factor_min    ?
_exptl_transmission_factor_max    ?
_exptl_crystal_size_max           0.25
_exptl_crystal_size_mid           0.25
_exptl_crystal_size_min           0.25
_exptl_absorpt_coefficient_mu     0.098
_shelx_estimated_absorpt_T_min    ?
_shelx_estimated_absorpt_T_max    ?
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.6912  
_exptl_absorpt_correction_T_max   0.7454
_exptl_absorpt_process_details    'SADABS V2014/4 (Bruker AXS Inc.)'
_exptl_absorpt_special_details    ?
_diffrn_ambient_temperature       100(2)
_diffrn_radiation_wavelength      0.71073
_diffrn_radiation_type            MoK\a
_diffrn_source                    ?
_diffrn_measurement_device_type   'Bruker APEX-II CCD'
_diffrn_measurement_method        'φ and ω scans'
_diffrn_detector_area_resol_mean  8.3333
_diffrn_reflns_number             16725
_diffrn_reflns_av_unetI/netI      0.0143
_diffrn_reflns_av_R_equivalents   0.0226
_diffrn_reflns_limit_h_min        -13
_diffrn_reflns_limit_h_max        13
_diffrn_reflns_limit_k_min        -18
_diffrn_reflns_limit_k_max        18
_diffrn_reflns_limit_l_min        -9
_diffrn_reflns_limit_l_max        9
_diffrn_reflns_theta_min          1.879
_diffrn_reflns_theta_max          26.477
_diffrn_reflns_theta_full         25.242
_diffrn_measured_fraction_theta_max   0.997
_diffrn_measured_fraction_theta_full  0.999
_diffrn_reflns_Laue_measured_fraction_max    0.997
_diffrn_reflns_Laue_measured_fraction_full   0.999
_diffrn_reflns_point_group_measured_fraction_max   0.997
_diffrn_reflns_point_group_measured_fraction_full  0.999
_reflns_number_total              2612
_reflns_number_gt                 2347
_reflns_threshold_expression      'I > 2σ(I)'
_reflns_Friedel_coverage          0.000
_reflns_Friedel_fraction_max      .
_reflns_Friedel_fraction_full     .
 
_reflns_special_details
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
 
_computing_data_collection        'Bruker APEX2'
_computing_cell_refinement        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction         'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution     ?
_computing_structure_refinement   'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics     'Bruker SHELXTL'
_computing_publication_material   'Bruker SHELXTL'
_refine_special_details           ?
_refine_ls_structure_factor_coef  Fsqd
_refine_ls_matrix_type            full
_refine_ls_weighting_scheme       calc
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0418P)²+0.4687P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary      ?
_atom_sites_solution_secondary    ?
_atom_sites_solution_hydrogens    geom
_refine_ls_hydrogen_treatment     constr
_refine_ls_extinction_method      none
_refine_ls_extinction_coef        .
_refine_ls_number_reflns          2612
_refine_ls_number_parameters      175
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0362
_refine_ls_R_factor_gt            0.0317
_refine_ls_wR_factor_ref          0.0852
_refine_ls_wR_factor_gt           0.0821
_refine_ls_goodness_of_fit_ref    1.058
_refine_ls_restrained_S_all       1.058
_refine_ls_shift/su_max           0.001
_refine_ls_shift/su_mean          0.000
 
loop_
 _atom_site_label
 _atom_site_type_symbol
 _atom_site_fract_x
 _atom_site_fract_y
 _atom_site_fract_z
 _atom_site_U_iso_or_equiv
 _atom_site_adp_type
 _atom_site_occupancy
 _atom_site_site_symmetry_order  
 _atom_site_calc_flag
 _atom_site_refinement_flags_posn
 _atom_site_refinement_flags_adp
 _atom_site_refinement_flags_occupancy
 _atom_site_disorder_assembly
 _atom_site_disorder_group
F1 F 0.13923(6) 0.95608(5) 0.15379(9) 0.02302(18) Uani 1 1 d . . . . .
O1 O 0.93300(7) 0.84637(6) 0.66910(10) 0.01889(19) Uani 1 1 d . . . . .
O2 O 0.86509(7) 0.91834(6) 0.36701(10) 0.01840(19) Uani 1 1 d . . . . .
C1 C 0.21935(10) 0.91978(7) 0.29271(14) 0.0165(2) Uani 1 1 d . . . . .
C2 C 0.34383(10) 0.92280(7) 0.28950(14) 0.0144(2) Uani 1 1 d . . . . .
H3 H 0.3730 0.9481 0.1939 0.017 Uiso 1 1 calc R U . . .
C3 C 0.42431(9) 0.88683(7) 0.43341(13) 0.0127(2) Uani 1 1 d . . . . .
C4 C 0.55947(9) 0.88094(7) 0.47375(13) 0.0125(2) Uani 1 1 d . . . . .
C5 C 0.64646(10) 0.90804(7) 0.37707(13) 0.0134(2) Uani 1 1 d . . . . .
H4 H 0.6209 0.9350 0.2654 0.016 Uiso 1 1 calc R U . . .
C6 C 0.77049(10) 0.89495(7) 0.44699(14) 0.0144(2) Uani 1 1 d . . . . .
C7 C 0.80803(10) 0.85452(7) 0.61384(14) 0.0147(2) Uani 1 1 d . . . . .
C8 C 0.97501(11) 0.81339(9) 0.84257(15) 0.0224(3) Uani 1 1 d . . . . .
H9 H 0.9441 0.8522 0.9254 0.034 Uiso 1 1 calc R U . . .
H1 H 1.0654 0.8131 0.8703 0.034 Uiso 1 1 calc R U . . .
H8 H 0.9443 0.7523 0.8510 0.034 Uiso 1 1 calc R U . . .
C9 C 0.17137(10) 0.88281(8) 0.42695(15) 0.0182(2) Uani 1 1 d . . . . .
H15 H 0.0850 0.8828 0.4232 0.022 Uiso 1 1 calc R U . . .
C10 C 0.25351(10) 0.84545(7) 0.56823(15) 0.0169(2) Uani 1 1 d . . . . .
H2 H 0.2234 0.8183 0.6613 0.020 Uiso 1 1 calc R U . . .
C11 C 0.37920(10) 0.84820(7) 0.57216(14) 0.0141(2) Uani 1 1 d . . . . .
C12 C 0.83270(11) 0.95984(8) 0.19955(15) 0.0205(3) Uani 1 1 d . . . . .
H6 H 0.7837 0.9181 0.1166 0.031 Uiso 1 1 calc R U . . .
H7 H 0.9079 0.9759 0.1586 0.031 Uiso 1 1 calc R U . . .
H5 H 0.7843 1.0140 0.2083 0.031 Uiso 1 1 calc R U . . .
C13 C 0.72068(10) 0.82676(7) 0.70768(14) 0.0147(2) Uani 1 1 d . . . . .
H10 H 0.7455 0.7990 0.8186 0.018 Uiso 1 1 calc R U . . .
C14 C 0.59592(10) 0.84029(7) 0.63653(14) 0.0135(2) Uani 1 1 d . . . . .
C15 C 0.48501(10) 0.81596(7) 0.71350(13) 0.0143(2) Uani 1 1 d . . . . .
H14 H 0.4803 0.7493 0.7234 0.017 Uiso 1 1 calc R U . . .
C16 C 0.48613(11) 0.85805(8) 0.89283(14) 0.0182(2) Uani 1 1 d . . . . .
H13 H 0.4893 0.9235 0.8834 0.027 Uiso 1 1 calc R U . . .
H12 H 0.5587 0.8369 0.9766 0.027 Uiso 1 1 calc R U . . .
H11 H 0.4111 0.8406 0.9330 0.027 Uiso 1 1 calc R U . . .
 
 
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
 
loop_
 _geom_bond_atom_site_label_1
 _geom_bond_atom_site_label_2
 _geom_bond_distance
 _geom_bond_site_symmetry_2
 _geom_bond_publ_flag
F1 C1 1.3671(12) . ?
O1 C7 1.3686(13) . ?
O1 C8 1.4286(13) . ?
O2 C6 1.3686(13) . ?
O2 C12 1.4264(13) . ?
C1 C9 1.3826(16) . ?
C1 C2 1.3838(15) . ?
C2 C3 1.3932(15) . ?
C2 H3 0.9500 . ?
C3 C11 1.4056(15) . ?
C3 C4 1.4679(14) . ?
C4 C14 1.3932(15) . ?
C4 C5 1.3983(15) . ?
C5 C6 1.3850(15) . ?
C5 H4 0.9500 . ?
C6 C7 1.4203(15) . ?
C7 C13 1.3894(16) . ?
C8 H9 0.9800 . ?
C8 H1 0.9800 . ?
C8 H8 0.9800 . ?
C9 C10 1.3966(16) . ?
C9 H15 0.9500 . ?
C10 C11 1.3859(15) . ?
C10 H2 0.9500 . ?
C11 C15 1.5165(14) . ?
C12 H6 0.9800 . ?
C12 H7 0.9800 . ?
C12 H5 0.9800 . ?
C13 C14 1.3952(15) . ?
C13 H10 0.9500 . ?
C14 C15 1.5162(15) . ?
C15 C16 1.5332(15) . ?
C15 H14 1.0000 . ?
C16 H13 0.9800 . ?
C16 H12 0.9800 . ?
C16 H11 0.9800 . ?
 
loop_
 _geom_angle_atom_site_label_1
 _geom_angle_atom_site_label_2
 _geom_angle_atom_site_label_3
 _geom_angle
 _geom_angle_site_symmetry_1
 _geom_angle_site_symmetry_3
 _geom_angle_publ_flag
C7 O1 C8 116.38(9) . . ?
C6 O2 C12 117.12(8) . . ?
F1 C1 C9 118.25(10) . . ?
F1 C1 C2 117.47(10) . . ?
C9 C1 C2 124.28(10) . . ?
C1 C2 C3 116.71(10) . . ?
C1 C2 H3 121.6 . . ?
C3 C2 H3 121.6 . . ?
C2 C3 C11 120.77(10) . . ?
C2 C3 C4 130.85(10) . . ?
C11 C3 C4 108.38(9) . . ?
C14 C4 C5 121.00(10) . . ?
C14 C4 C3 108.46(9) . . ?
C5 C4 C3 130.54(10) . . ?
C6 C5 C4 118.82(10) . . ?
C6 C5 H4 120.6 . . ?
C4 C5 H4 120.6 . . ?
O2 C6 C5 124.95(10) . . ?
O2 C6 C7 114.74(9) . . ?
C5 C6 C7 120.31(10) . . ?
O1 C7 C13 125.01(10) . . ?
O1 C7 C6 114.63(10) . . ?
C13 C7 C6 120.35(10) . . ?
O1 C8 H9 109.5 . . ?
O1 C8 H1 109.5 . . ?
H9 C8 H1 109.5 . . ?
O1 C8 H8 109.5 . . ?
H9 C8 H8 109.5 . . ?
H1 C8 H8 109.5 . . ?
C1 C9 C10 118.06(10) . . ?
C1 C9 H15 121.0 . . ?
C10 C9 H15 121.0 . . ?
C11 C10 C9 119.73(10) . . ?
C11 C10 H2 120.1 . . ?
C9 C10 H2 120.1 . . ?
C10 C11 C3 120.43(10) . . ?
C10 C11 C15 129.11(10) . . ?
C3 C11 C15 110.44(9) . . ?
O2 C12 H6 109.5 . . ?
O2 C12 H7 109.5 . . ?
H6 C12 H7 109.5 . . ?
O2 C12 H5 109.5 . . ?
H6 C12 H5 109.5 . . ?
H7 C12 H5 109.5 . . ?
C7 C13 C14 119.01(10) . . ?
C7 C13 H10 120.5 . . ?
C14 C13 H10 120.5 . . ?
C4 C14 C13 120.50(10) . . ?
C4 C14 C15 110.98(9) . . ?
C13 C14 C15 128.53(10) . . ?
C14 C15 C11 101.73(8) . . ?
C14 C15 C16 114.00(9) . . ?
C11 C15 C16 113.46(9) . . ?
C14 C15 H14 109.1 . . ?
C11 C15 H14 109.1 . . ?
C16 C15 H14 109.1 . . ?
C15 C16 H13 109.5 . . ?
C15 C16 H12 109.5 . . ?
H13 C16 H12 109.5 . . ?
C15 C16 H11 109.5 . . ?
H13 C16 H11 109.5 . . ?
H12 C16 H11 109.5 . . ?
 
_refine_diff_density_max    0.275
_refine_diff_density_min   -0.203
_refine_diff_density_rms    0.039

_shelxl_version_number 2014/6



 
data_181210LT_a
 
_audit_creation_method            SHELXL-2014/6
_chemical_name_systematic         ?
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C19 H22 Cl2 O4' 
_chemical_formula_weight          385.26

loop_
 _atom_type_symbol
 _atom_type_description
 _atom_type_scat_dispersion_real
 _atom_type_scat_dispersion_imag
 _atom_type_scat_source
 'C'  'C'   0.0033   0.0016
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'H'  'H'   0.0000   0.0000
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'O'  'O'   0.0106   0.0060
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'Cl'  'Cl'   0.1484   0.1585
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 
_space_group_crystal_system       orthorhombic
_space_group_IT_number            31
_space_group_name_H-M_alt         'P m n 21'
_space_group_name_Hall            'P 2ac -2'
 
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
 
loop_
 _space_group_symop_operation_xyz
 'x, y, z'
 '-x+1/2, -y, z+1/2'
 'x+1/2, -y, z+1/2'
 '-x, y, z'
 
_cell_length_a                    14.7692(17)
_cell_length_b                    10.2619(12)
_cell_length_c                    5.9666(6)
_cell_angle_alpha                 90
_cell_angle_beta                  90
_cell_angle_gamma                 90
_cell_volume                      904.30(17)
_cell_formula_units_Z             2
_cell_measurement_temperature     100(2)
_cell_measurement_reflns_used     6148
_cell_measurement_theta_min       2.4168
_cell_measurement_theta_max       26.5106
 
_exptl_crystal_description        lump
_exptl_crystal_colour             colorless
_exptl_crystal_density_meas       'not measured'
_exptl_crystal_density_method     'not measured'
_exptl_crystal_density_diffrn     1.415          
_exptl_crystal_F_000              404
_exptl_transmission_factor_min    ?
_exptl_transmission_factor_max    ?
_exptl_crystal_size_max           0.25
_exptl_crystal_size_mid           0.24
_exptl_crystal_size_min           0.20
_exptl_absorpt_coefficient_mu     0.380
_shelx_estimated_absorpt_T_min    ?
_shelx_estimated_absorpt_T_max    ?
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.5637  
_exptl_absorpt_correction_T_max   0.7454
_exptl_absorpt_process_details    'SADABS V2014/4 (Bruker AXS Inc.)'
_exptl_absorpt_special_details    ?
_diffrn_ambient_temperature       100(2)
_diffrn_radiation_wavelength      0.71073
_diffrn_radiation_type            MoK\a
_diffrn_source                    ?
_diffrn_measurement_device_type   'Bruker APEX-II CCD'
_diffrn_measurement_method        'φ and ω scans'
_diffrn_detector_area_resol_mean  8.3333
_diffrn_reflns_number             10238
_diffrn_reflns_av_unetI/netI      0.0346
_diffrn_reflns_av_R_equivalents   0.0451
_diffrn_reflns_limit_h_min        -18
_diffrn_reflns_limit_h_max        18
_diffrn_reflns_limit_k_min        -11
_diffrn_reflns_limit_k_max        12
_diffrn_reflns_limit_l_min        -7
_diffrn_reflns_limit_l_max        7
_diffrn_reflns_theta_min          1.985
_diffrn_reflns_theta_max          26.640
_diffrn_reflns_theta_full         25.242
_diffrn_measured_fraction_theta_max   0.992
_diffrn_measured_fraction_theta_full  1.000
_diffrn_reflns_Laue_measured_fraction_max    0.992
_diffrn_reflns_Laue_measured_fraction_full   1.000
_diffrn_reflns_point_group_measured_fraction_max   0.991
_diffrn_reflns_point_group_measured_fraction_full  1.000
_reflns_number_total              1903
_reflns_number_gt                 1847
_reflns_threshold_expression      'I > 2σ(I)'
_reflns_Friedel_coverage          0.819
_reflns_Friedel_fraction_max      0.990
_reflns_Friedel_fraction_full     1.000
 
_reflns_special_details
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
 
_computing_data_collection        'Bruker APEX2'
_computing_cell_refinement        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction         'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution     ?
_computing_structure_refinement   'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics     'Bruker SHELXTL'
_computing_publication_material   'Bruker SHELXTL'
_refine_special_details
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef  Fsqd
_refine_ls_matrix_type            full
_refine_ls_weighting_scheme       calc
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0463P)²+0.1676P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary      ?
_atom_sites_solution_secondary    ?
_atom_sites_solution_hydrogens    mixed
_refine_ls_hydrogen_treatment     constr
_refine_ls_extinction_method      none
_refine_ls_extinction_coef        .
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack    0.25(8)
_chemical_absolute_configuration  rm
_refine_ls_number_reflns          1903
_refine_ls_number_parameters      124
_refine_ls_number_restraints      1
_refine_ls_R_factor_all           0.0304
_refine_ls_R_factor_gt            0.0293
_refine_ls_wR_factor_ref          0.0795
_refine_ls_wR_factor_gt           0.0788
_refine_ls_goodness_of_fit_ref    1.064
_refine_ls_restrained_S_all       1.063
_refine_ls_shift/su_max           0.003
_refine_ls_shift/su_mean          0.000
 
loop_
 _atom_site_label
 _atom_site_type_symbol
 _atom_site_fract_x
 _atom_site_fract_y
 _atom_site_fract_z
 _atom_site_U_iso_or_equiv
 _atom_site_adp_type
 _atom_site_occupancy
 _atom_site_site_symmetry_order  
 _atom_site_calc_flag
 _atom_site_refinement_flags_posn
 _atom_site_refinement_flags_adp
 _atom_site_refinement_flags_occupancy
 _atom_site_disorder_assembly
 _atom_site_disorder_group
Cl2 Cl 0.0000 0.90598(8) 0.81697(15) 0.0221(2) Uani 1 2 d S T P . .
Cl1 Cl 0.0000 1.03036(9) 0.37560(16) 0.0291(3) Uani 1 2 d S T P . .
O1 O 0.82474(11) 0.68967(17) 0.6653(3) 0.0162(4) Uani 1 1 d . . . . .
O2 O 0.77269(10) 0.82385(16) 0.3260(3) 0.0159(4) Uani 1 1 d . . . . .
C3 C 0.73309(15) 0.6916(2) 0.6310(4) 0.0131(5) Uani 1 1 d . . . . .
C4 C 0.70420(16) 0.7658(2) 0.4438(4) 0.0138(5) Uani 1 1 d . . . . .
C5 C 0.61272(14) 0.7763(2) 0.3935(4) 0.0132(5) Uani 1 1 d . . . . .
H5 H 0.5932 0.8243 0.2663 0.016 Uiso 1 1 calc R U . . .
C1 C 0.57905(15) 0.6424(2) 0.7186(4) 0.0144(5) Uani 1 1 d . . . . .
C6 C 0.54974(15) 0.7147(2) 0.5334(5) 0.0137(5) Uani 1 1 d . . . . .
C2 C 0.67068(15) 0.6288(2) 0.7664(4) 0.0138(5) Uani 1 1 d . . . . .
H2 H 0.6901 0.5774 0.8897 0.017 Uiso 1 1 calc R U . . .
C7 C 0.5000 0.5867(3) 0.8487(7) 0.0158(7) Uani 1 2 d S T P . .
H7 H 0.5000 0.6220 1.0049 0.019 Uiso 1 2 calc R U P . .
C9 C 0.85566(15) 0.6158(2) 0.8536(5) 0.0193(5) Uani 1 1 d . . . . .
H9A H 0.8295 0.6518 0.9913 0.029 Uiso 1 1 calc R U . . .
H9B H 0.9219 0.6203 0.8619 0.029 Uiso 1 1 calc R U . . .
H9C H 0.8368 0.5248 0.8367 0.029 Uiso 1 1 calc R U . . .
C10 C 0.74725(16) 0.9084(3) 0.1449(5) 0.0174(5) Uani 1 1 d . . . . .
H10A H 0.7150 0.8580 0.0304 0.026 Uiso 1 1 calc R U . . .
H10B H 0.8017 0.9473 0.0790 0.026 Uiso 1 1 calc R U . . .
H10C H 0.7077 0.9775 0.2017 0.026 Uiso 1 1 calc R U . . .
C8 C 0.5000 0.4390(3) 0.8547(7) 0.0193(8) Uani 1 2 d S T P . .
C11 C 0.0000 0.8802(4) 0.5235(6) 0.0201(8) Uani 1 2 d S T P . .
H11A H -0.0542 0.8292 0.4811 0.024 Uiso 0.5 1 calc R U P . .
H11B H 0.0542 0.8292 0.4811 0.024 Uiso 0.5 1 calc R U P . .
H8A H 0.5000 0.4061 0.7028 0.080 Uiso 1 2 d S . P . .
H8B H 0.4490 0.4036 0.9436 0.080 Uiso 1 1 d . . . . .
 
 
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
 
loop_
 _geom_bond_atom_site_label_1
 _geom_bond_atom_site_label_2
 _geom_bond_distance
 _geom_bond_site_symmetry_2
 _geom_bond_publ_flag
Cl2 C11 1.771(4) . ?
Cl1 C11 1.775(4) . ?
O1 C3 1.369(3) . ?
O1 C9 1.430(3) . ?
O2 C4 1.369(3) . ?
O2 C10 1.436(3) . ?
C3 C2 1.385(3) . ?
C3 C4 1.417(4) . ?
C4 C5 1.388(3) . ?
C5 C6 1.401(3) . ?
C5 H5 0.9500 . ?
C1 C2 1.390(3) . ?
C1 C6 1.399(4) . ?
C1 C7 1.515(3) . ?
C6 C6 1.469(4) 4_655 ?
C2 H2 0.9500 . ?
C7 C1 1.515(3) 4_655 ?
C7 C8 1.516(5) . ?
C7 H7 1.0000 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C8 H8A 0.9674 . ?
C8 H8B 0.9902 . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
 
loop_
 _geom_angle_atom_site_label_1
 _geom_angle_atom_site_label_2
 _geom_angle_atom_site_label_3
 _geom_angle
 _geom_angle_site_symmetry_1
 _geom_angle_site_symmetry_3
 _geom_angle_publ_flag
C3 O1 C9 116.15(18) . . ?
C4 O2 C10 117.16(18) . . ?
O1 C3 C2 124.3(2) . . ?
O1 C3 C4 115.0(2) . . ?
C2 C3 C4 120.6(2) . . ?
O2 C4 C5 125.1(2) . . ?
O2 C4 C3 114.6(2) . . ?
C5 C4 C3 120.3(2) . . ?
C4 C5 C6 118.8(2) . . ?
C4 C5 H5 120.6 . . ?
C6 C5 H5 120.6 . . ?
C2 C1 C6 121.1(2) . . ?
C2 C1 C7 127.4(2) . . ?
C6 C1 C7 111.5(2) . . ?
C1 C6 C5 120.3(2) . . ?
C1 C6 C6 108.03(13) . 4_655 ?
C5 C6 C6 131.62(14) . 4_655 ?
C3 C2 C1 118.8(2) . . ?
C3 C2 H2 120.6 . . ?
C1 C2 H2 120.6 . . ?
C1 C7 C1 100.9(3) . 4_655 ?
C1 C7 C8 112.9(2) . . ?
C1 C7 C8 112.9(2) 4_655 . ?
C1 C7 H7 109.9 . . ?
C1 C7 H7 109.9 4_655 . ?
C8 C7 H7 109.9 . . ?
O1 C9 H9A 109.5 . . ?
O1 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
O1 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
O2 C10 H10A 109.5 . . ?
O2 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
O2 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C7 C8 H8A 109.1 . . ?
C7 C8 H8B 112.3 . . ?
H8A C8 H8B 111.9 . . ?
Cl2 C11 Cl1 111.2(2) . . ?
Cl2 C11 H11A 109.4 . . ?
Cl1 C11 H11A 109.4 . . ?
Cl2 C11 H11B 109.4 . . ?
Cl1 C11 H11B 109.4 . . ?
H11A C11 H11B 108.0 . . ?
 
_refine_diff_density_max    0.380
_refine_diff_density_min   -0.234
_refine_diff_density_rms    0.048

_shelxl_version_number 2014/6



 
data_mo_180820LT_0m
 
_audit_creation_method            SHELXL-2014/6
_chemical_name_systematic         ?
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C23 H20 O4 S' 
_chemical_formula_weight          392.45

loop_
 _atom_type_symbol
 _atom_type_description
 _atom_type_scat_dispersion_real
 _atom_type_scat_dispersion_imag
 _atom_type_scat_source
 'C'  'C'   0.0033   0.0016
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'H'  'H'   0.0000   0.0000
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'O'  'O'   0.0106   0.0060
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'S'  'S'   0.1246   0.1234
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 
_space_group_crystal_system       monoclinic
_space_group_IT_number            13
_space_group_name_H-M_alt         'P 2/c'
_space_group_name_Hall            '-P 2yc'
 
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
 
loop_
 _space_group_symop_operation_xyz
 'x, y, z'
 '-x, y, -z+1/2'
 '-x, -y, -z'
 'x, -y, z-1/2'
 
_cell_length_a                    8.3017(5)
_cell_length_b                    10.3840(6)
_cell_length_c                    21.3810(12)
_cell_angle_alpha                 90
_cell_angle_beta                  94.188(3)
_cell_angle_gamma                 90
_cell_volume                      1838.22(19)
_cell_formula_units_Z             4
_cell_measurement_temperature     99(2)
_cell_measurement_reflns_used     9339
_cell_measurement_theta_min       2.1815
_cell_measurement_theta_max       26.3875
 
_exptl_crystal_description        Lump
_exptl_crystal_colour             Red
_exptl_crystal_density_meas       'not measured'
_exptl_crystal_density_method     'not measured'
_exptl_crystal_density_diffrn     1.418          
_exptl_crystal_F_000              824
_exptl_transmission_factor_min    ?
_exptl_transmission_factor_max    ?
_exptl_crystal_size_max           0.22
_exptl_crystal_size_mid           0.20
_exptl_crystal_size_min           0.20
_exptl_absorpt_coefficient_mu     0.204
_shelx_estimated_absorpt_T_min    ?
_shelx_estimated_absorpt_T_max    ?
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.7181  
_exptl_absorpt_correction_T_max   0.7454
_exptl_absorpt_process_details    'SADABS V2014/4 (Bruker AXS Inc.)'
_exptl_absorpt_special_details    ?
_diffrn_ambient_temperature       99(2)
_diffrn_radiation_wavelength      0.71073
_diffrn_radiation_type            MoK\a
_diffrn_source                    ?
_diffrn_measurement_device_type   'Bruker APEX-II CCD'
_diffrn_measurement_method        'φ and ω scans'
_diffrn_detector_area_resol_mean  8.3333
_diffrn_reflns_number             24716
_diffrn_reflns_av_unetI/netI      0.0242
_diffrn_reflns_av_R_equivalents   0.0343
_diffrn_reflns_limit_h_min        -10
_diffrn_reflns_limit_h_max        10
_diffrn_reflns_limit_k_min        -12
_diffrn_reflns_limit_k_max        12
_diffrn_reflns_limit_l_min        -24
_diffrn_reflns_limit_l_max        26
_diffrn_reflns_theta_min          1.910
_diffrn_reflns_theta_max          26.462
_diffrn_reflns_theta_full         25.242
_diffrn_measured_fraction_theta_max   0.996
_diffrn_measured_fraction_theta_full  0.998
_diffrn_reflns_Laue_measured_fraction_max    0.996
_diffrn_reflns_Laue_measured_fraction_full   0.998
_diffrn_reflns_point_group_measured_fraction_max   0.996
_diffrn_reflns_point_group_measured_fraction_full  0.998
_reflns_number_total              3795
_reflns_number_gt                 3308
_reflns_threshold_expression      'I > 2σ(I)'
_reflns_Friedel_coverage          0.000
_reflns_Friedel_fraction_max      .
_reflns_Friedel_fraction_full     .
 
_reflns_special_details
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
 
_computing_data_collection        'Bruker APEX2'
_computing_cell_refinement        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction         'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution     ?
_computing_structure_refinement   'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics     'Bruker SHELXTL'
_computing_publication_material   'Bruker SHELXTL'
_refine_special_details           ?
_refine_ls_structure_factor_coef  Fsqd
_refine_ls_matrix_type            full
_refine_ls_weighting_scheme       calc
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0433P)²+0.8974P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary      ?
_atom_sites_solution_secondary    ?
_atom_sites_solution_hydrogens    geom
_refine_ls_hydrogen_treatment     constr
_refine_ls_extinction_method      none
_refine_ls_extinction_coef        .
_refine_ls_number_reflns          3795
_refine_ls_number_parameters      256
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0385
_refine_ls_R_factor_gt            0.0324
_refine_ls_wR_factor_ref          0.0891
_refine_ls_wR_factor_gt           0.0847
_refine_ls_goodness_of_fit_ref    1.045
_refine_ls_restrained_S_all       1.045
_refine_ls_shift/su_max           0.000
_refine_ls_shift/su_mean          0.000
 
loop_
 _atom_site_label
 _atom_site_type_symbol
 _atom_site_fract_x
 _atom_site_fract_y
 _atom_site_fract_z
 _atom_site_U_iso_or_equiv
 _atom_site_adp_type
 _atom_site_occupancy
 _atom_site_site_symmetry_order  
 _atom_site_calc_flag
 _atom_site_refinement_flags_posn
 _atom_site_refinement_flags_adp
 _atom_site_refinement_flags_occupancy
 _atom_site_disorder_assembly
 _atom_site_disorder_group
S1 S 0.67958(4) 0.17181(3) 0.19144(2) 0.01665(11) Uani 1 1 d . . . . .
O1 O 0.43935(12) 0.80047(9) 0.07164(5) 0.0193(2) Uani 1 1 d . . . . .
O2 O 0.52206(12) 0.19473(9) 0.16103(5) 0.0206(2) Uani 1 1 d . . . . .
O3 O 0.36150(12) 0.56842(10) 0.04542(4) 0.0193(2) Uani 1 1 d . . . . .
O4 O 0.70720(13) 0.05709(10) 0.22869(5) 0.0229(2) Uani 1 1 d . . . . .
C1 C 0.47247(19) 0.93167(14) 0.08776(7) 0.0223(3) Uani 1 1 d . . . . .
H11 H 0.4314 0.9506 0.1286 0.034 Uiso 1 1 calc R U . . .
H1 H 0.4194 0.9881 0.0558 0.034 Uiso 1 1 calc R U . . .
H10 H 0.5893 0.9464 0.0900 0.034 Uiso 1 1 calc R U . . .
C2 C 0.50494(16) 0.71163(13) 0.11267(6) 0.0148(3) Uani 1 1 d . . . . .
C3 C 0.60238(16) 0.74023(13) 0.16610(6) 0.0145(3) Uani 1 1 d . . . . .
H12 H 0.6262 0.8270 0.1773 0.017 Uiso 1 1 calc R U . . .
C4 C 0.66457(15) 0.63931(13) 0.20292(6) 0.0135(3) Uani 1 1 d . . . . .
C5 C 0.63263(16) 0.51066(13) 0.18684(6) 0.0138(3) Uani 1 1 d . . . . .
C6 C 0.72258(15) 0.42774(13) 0.23362(6) 0.0138(3) Uani 1 1 d . . . . .
C7 C 0.74460(17) 0.30012(13) 0.24004(6) 0.0165(3) Uani 1 1 d . . . . .
H6 H 0.8060 0.2753 0.2773 0.020 Uiso 1 1 calc R U . . .
C8 C 0.82018(16) 0.16909(12) 0.13317(6) 0.0155(3) Uani 1 1 d . . . . .
C9 C 0.78241(17) 0.22148(14) 0.07420(7) 0.0185(3) Uani 1 1 d . . . . .
H5 H 0.6797 0.2597 0.0643 0.022 Uiso 1 1 calc R U . . .
C10 C 0.89595(17) 0.21747(14) 0.02979(6) 0.0181(3) Uani 1 1 d . . . . .
H4 H 0.8699 0.2524 -0.0108 0.022 Uiso 1 1 calc R U . . .
C11 C 1.04753(17) 0.16308(13) 0.04375(6) 0.0167(3) Uani 1 1 d . . . . .
C12 C 1.16907(17) 0.15407(14) -0.00504(7) 0.0196(3) Uani 1 1 d . . . . .
H2 H 1.1596 0.0700 -0.0258 0.029 Uiso 1 1 calc R U . . .
H20 H 1.2782 0.1639 0.0151 0.029 Uiso 1 1 calc R U . . .
H3 H 1.1485 0.2224 -0.0362 0.029 Uiso 1 1 calc R U . . .
C13 C 0.80544(15) 0.51833(13) 0.27945(6) 0.0141(3) Uani 1 1 d . . . . .
C14 C 0.90773(16) 0.49455(14) 0.33231(6) 0.0178(3) Uani 1 1 d . . . . .
H17 H 0.9344 0.4089 0.3448 0.021 Uiso 1 1 calc R U . . .
C15 C 0.97042(17) 0.59900(15) 0.36667(6) 0.0208(3) Uani 1 1 d . . . . .
H16 H 1.0404 0.5844 0.4032 0.025 Uiso 1 1 calc R U . . .
C16 C 0.93233(17) 0.72466(15) 0.34847(7) 0.0204(3) Uani 1 1 d . . . . .
H15 H 0.9758 0.7946 0.3729 0.025 Uiso 1 1 calc R U . . .
C17 C 0.83146(17) 0.74902(14) 0.29499(6) 0.0175(3) Uani 1 1 d . . . . .
H14 H 0.8058 0.8347 0.2823 0.021 Uiso 1 1 calc R U . . .
C18 C 0.76945(15) 0.64471(13) 0.26079(6) 0.0142(3) Uani 1 1 d . . . . .
C19 C 0.52923(15) 0.48219(13) 0.13396(6) 0.0144(3) Uani 1 1 d . . . . .
H13 H 0.5035 0.3954 0.1233 0.017 Uiso 1 1 calc R U . . .
C20 C 0.46534(16) 0.58234(13) 0.09767(6) 0.0147(3) Uani 1 1 d . . . . .
C21 C 0.30935(18) 0.44093(14) 0.03039(7) 0.0220(3) Uani 1 1 d . . . . .
H7 H 0.4028 0.3880 0.0215 0.033 Uiso 1 1 calc R U . . .
H8 H 0.2324 0.4428 -0.0066 0.033 Uiso 1 1 calc R U . . .
H9 H 0.2569 0.4041 0.0659 0.033 Uiso 1 1 calc R U . . .
C22 C 0.97062(17) 0.11402(14) 0.14798(7) 0.0190(3) Uani 1 1 d . . . . .
H19 H 0.9957 0.0777 0.1883 0.023 Uiso 1 1 calc R U . . .
C23 C 1.08341(17) 0.11253(14) 0.10357(7) 0.0202(3) Uani 1 1 d . . . . .
H18 H 1.1871 0.0765 0.1139 0.024 Uiso 1 1 calc R U . . .
 
 
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
 
loop_
 _geom_bond_atom_site_label_1
 _geom_bond_atom_site_label_2
 _geom_bond_distance
 _geom_bond_site_symmetry_2
 _geom_bond_publ_flag
S1 O2 1.4371(11) . ?
S1 O4 1.4420(10) . ?
S1 C7 1.7504(14) . ?
S1 C8 1.7687(14) . ?
O1 C2 1.3592(16) . ?
O1 C1 1.4271(17) . ?
O3 C20 1.3681(15) . ?
O3 C21 1.4223(17) . ?
C1 H11 0.9800 . ?
C1 H1 0.9800 . ?
C1 H10 0.9800 . ?
C2 C3 1.3830(18) . ?
C2 C20 1.4135(19) . ?
C3 C4 1.3875(19) . ?
C3 H12 0.9500 . ?
C4 C5 1.3999(19) . ?
C4 C18 1.4611(18) . ?
C5 C19 1.4002(18) . ?
C5 C6 1.4800(18) . ?
C6 C7 1.3434(19) . ?
C6 C13 1.4899(18) . ?
C7 H6 0.9500 . ?
C8 C9 1.3880(19) . ?
C8 C22 1.3889(19) . ?
C9 C10 1.386(2) . ?
C9 H5 0.9500 . ?
C10 C11 1.3917(19) . ?
C10 H4 0.9500 . ?
C11 C23 1.394(2) . ?
C11 C12 1.5062(19) . ?
C12 H2 0.9800 . ?
C12 H20 0.9800 . ?
C12 H3 0.9800 . ?
C13 C14 1.3854(18) . ?
C13 C18 1.3975(19) . ?
C14 C15 1.390(2) . ?
C14 H17 0.9500 . ?
C15 C16 1.391(2) . ?
C15 H16 0.9500 . ?
C16 C17 1.3902(19) . ?
C16 H15 0.9500 . ?
C17 C18 1.3849(19) . ?
C17 H14 0.9500 . ?
C19 C20 1.3802(19) . ?
C19 H13 0.9500 . ?
C21 H7 0.9800 . ?
C21 H8 0.9800 . ?
C21 H9 0.9800 . ?
C22 C23 1.382(2) . ?
C22 H19 0.9500 . ?
C23 H18 0.9500 . ?
 
loop_
 _geom_angle_atom_site_label_1
 _geom_angle_atom_site_label_2
 _geom_angle_atom_site_label_3
 _geom_angle
 _geom_angle_site_symmetry_1
 _geom_angle_site_symmetry_3
 _geom_angle_publ_flag
O2 S1 O4 119.30(6) . . ?
O2 S1 C7 111.93(6) . . ?
O4 S1 C7 105.74(7) . . ?
O2 S1 C8 108.02(6) . . ?
O4 S1 C8 106.82(6) . . ?
C7 S1 C8 103.86(6) . . ?
C2 O1 C1 115.54(11) . . ?
C20 O3 C21 116.49(11) . . ?
O1 C1 H11 109.5 . . ?
O1 C1 H1 109.5 . . ?
H11 C1 H1 109.5 . . ?
O1 C1 H10 109.5 . . ?
H11 C1 H10 109.5 . . ?
H1 C1 H10 109.5 . . ?
O1 C2 C3 124.75(12) . . ?
O1 C2 C20 115.00(11) . . ?
C3 C2 C20 120.24(12) . . ?
C2 C3 C4 118.52(12) . . ?
C2 C3 H12 120.7 . . ?
C4 C3 H12 120.7 . . ?
C3 C4 C5 121.70(12) . . ?
C3 C4 C18 128.72(12) . . ?
C5 C4 C18 109.58(12) . . ?
C4 C5 C19 119.59(12) . . ?
C4 C5 C6 108.18(12) . . ?
C19 C5 C6 132.23(13) . . ?
C7 C6 C5 134.52(13) . . ?
C7 C6 C13 120.19(12) . . ?
C5 C6 C13 105.25(11) . . ?
C6 C7 S1 131.03(11) . . ?
C6 C7 H6 114.5 . . ?
S1 C7 H6 114.5 . . ?
C9 C8 C22 120.55(13) . . ?
C9 C8 S1 121.12(11) . . ?
C22 C8 S1 118.33(11) . . ?
C10 C9 C8 119.38(13) . . ?
C10 C9 H5 120.3 . . ?
C8 C9 H5 120.3 . . ?
C9 C10 C11 120.98(13) . . ?
C9 C10 H4 119.5 . . ?
C11 C10 H4 119.5 . . ?
C10 C11 C23 118.60(13) . . ?
C10 C11 C12 121.17(13) . . ?
C23 C11 C12 120.19(12) . . ?
C11 C12 H2 109.5 . . ?
C11 C12 H20 109.5 . . ?
H2 C12 H20 109.5 . . ?
C11 C12 H3 109.5 . . ?
H2 C12 H3 109.5 . . ?
H20 C12 H3 109.5 . . ?
C14 C13 C18 120.38(13) . . ?
C14 C13 C6 130.54(13) . . ?
C18 C13 C6 109.05(11) . . ?
C13 C14 C15 118.41(13) . . ?
C13 C14 H17 120.8 . . ?
C15 C14 H17 120.8 . . ?
C14 C15 C16 121.02(13) . . ?
C14 C15 H16 119.5 . . ?
C16 C15 H16 119.5 . . ?
C17 C16 C15 120.78(13) . . ?
C17 C16 H15 119.6 . . ?
C15 C16 H15 119.6 . . ?
C18 C17 C16 118.05(13) . . ?
C18 C17 H14 121.0 . . ?
C16 C17 H14 121.0 . . ?
C17 C18 C13 121.35(12) . . ?
C17 C18 C4 130.74(13) . . ?
C13 C18 C4 107.90(11) . . ?
C20 C19 C5 118.85(12) . . ?
C20 C19 H13 120.6 . . ?
C5 C19 H13 120.6 . . ?
O3 C20 C19 124.95(12) . . ?
O3 C20 C2 114.07(12) . . ?
C19 C20 C2 120.98(12) . . ?
O3 C21 H7 109.5 . . ?
O3 C21 H8 109.5 . . ?
H7 C21 H8 109.5 . . ?
O3 C21 H9 109.5 . . ?
H7 C21 H9 109.5 . . ?
H8 C21 H9 109.5 . . ?
C23 C22 C8 119.42(13) . . ?
C23 C22 H19 120.3 . . ?
C8 C22 H19 120.3 . . ?
C22 C23 C11 121.07(13) . . ?
C22 C23 H18 119.5 . . ?
C11 C23 H18 119.5 . . ?
 
_refine_diff_density_max    0.347
_refine_diff_density_min   -0.398
_refine_diff_density_rms    0.046

_shelxl_version_number 2014/6



 
data_mo_180858LT_0m
 
_audit_creation_method            SHELXL-2014/6
_chemical_name_systematic         ?
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C22 H17 F O4 S' 
_chemical_formula_weight          396.41

loop_
 _atom_type_symbol
 _atom_type_description
 _atom_type_scat_dispersion_real
 _atom_type_scat_dispersion_imag
 _atom_type_scat_source
 'C'  'C'   0.0033   0.0016
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'H'  'H'   0.0000   0.0000
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'O'  'O'   0.0106   0.0060
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'F'  'F'   0.0171   0.0103
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'S'  'S'   0.1246   0.1234
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 
_space_group_crystal_system       monoclinic
_space_group_IT_number            13
_space_group_name_H-M_alt         'P 2/c'
_space_group_name_Hall            '-P 2yc'
 
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
 
loop_
 _space_group_symop_operation_xyz
 'x, y, z'
 '-x, y, -z+1/2'
 '-x, -y, -z'
 'x, -y, z-1/2'
 
_cell_length_a                    8.3081(3)
_cell_length_b                    10.2495(3)
_cell_length_c                    20.9221(7)
_cell_angle_alpha                 90
_cell_angle_beta                  94.604(2)
_cell_angle_gamma                 90
_cell_volume                      1775.85(10)
_cell_formula_units_Z             4
_cell_measurement_temperature     99(2)
_cell_measurement_reflns_used     5166
_cell_measurement_theta_min       2.2140
_cell_measurement_theta_max       26.2714
 
_exptl_crystal_description        columnar
_exptl_crystal_colour             red
_exptl_crystal_density_meas       'not measured'
_exptl_crystal_density_method     'not measured'
_exptl_crystal_density_diffrn     1.483          
_exptl_crystal_F_000              824
_exptl_transmission_factor_min    ?
_exptl_transmission_factor_max    ?
_exptl_crystal_size_max           0.15
_exptl_crystal_size_mid           0.05
_exptl_crystal_size_min           0.05
_exptl_absorpt_coefficient_mu     0.220
_shelx_estimated_absorpt_T_min    ?
_shelx_estimated_absorpt_T_max    ?
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.7137  
_exptl_absorpt_correction_T_max   0.7454
_exptl_absorpt_process_details    'SADABS V2014/4 (Bruker AXS Inc.)'
_exptl_absorpt_special_details    ?
_diffrn_ambient_temperature       99(2)
_diffrn_radiation_wavelength      0.71073
_diffrn_radiation_type            MoK\a
_diffrn_source                    ?
_diffrn_measurement_device_type   'Bruker APEX-II CCD'
_diffrn_measurement_method        'φ and ω scans'
_diffrn_detector_area_resol_mean  8.3333
_diffrn_reflns_number             20038
_diffrn_reflns_av_unetI/netI      0.0302
_diffrn_reflns_av_R_equivalents   0.0381
_diffrn_reflns_limit_h_min        -10
_diffrn_reflns_limit_h_max        10
_diffrn_reflns_limit_k_min        -12
_diffrn_reflns_limit_k_max        12
_diffrn_reflns_limit_l_min        -25
_diffrn_reflns_limit_l_max        26
_diffrn_reflns_theta_min          1.953
_diffrn_reflns_theta_max          26.448
_diffrn_reflns_theta_full         25.242
_diffrn_measured_fraction_theta_max   0.998
_diffrn_measured_fraction_theta_full  1.000
_diffrn_reflns_Laue_measured_fraction_max    0.998
_diffrn_reflns_Laue_measured_fraction_full   1.000
_diffrn_reflns_point_group_measured_fraction_max   0.998
_diffrn_reflns_point_group_measured_fraction_full  1.000
_reflns_number_total              3665
_reflns_number_gt                 2880
_reflns_threshold_expression      'I > 2σ(I)'
_reflns_Friedel_coverage          0.000
_reflns_Friedel_fraction_max      .
_reflns_Friedel_fraction_full     .
 
_reflns_special_details
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
 
_computing_data_collection        'Bruker APEX2'
_computing_cell_refinement        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction         'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution     ?
_computing_structure_refinement   'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics     'Bruker SHELXTL'
_computing_publication_material   'Bruker SHELXTL'
_refine_special_details           ?
_refine_ls_structure_factor_coef  Fsqd
_refine_ls_matrix_type            full
_refine_ls_weighting_scheme       calc
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0560P)²+1.7804P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary      ?
_atom_sites_solution_secondary    ?
_atom_sites_solution_hydrogens    geom
_refine_ls_hydrogen_treatment     constr
_refine_ls_extinction_method      none
_refine_ls_extinction_coef        .
_refine_ls_number_reflns          3665
_refine_ls_number_parameters      255
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0615
_refine_ls_R_factor_gt            0.0448
_refine_ls_wR_factor_ref          0.1210
_refine_ls_wR_factor_gt           0.1119
_refine_ls_goodness_of_fit_ref    1.023
_refine_ls_restrained_S_all       1.023
_refine_ls_shift/su_max           0.001
_refine_ls_shift/su_mean          0.000
 
loop_
 _atom_site_label
 _atom_site_type_symbol
 _atom_site_fract_x
 _atom_site_fract_y
 _atom_site_fract_z
 _atom_site_U_iso_or_equiv
 _atom_site_adp_type
 _atom_site_occupancy
 _atom_site_site_symmetry_order  
 _atom_site_calc_flag
 _atom_site_refinement_flags_posn
 _atom_site_refinement_flags_adp
 _atom_site_refinement_flags_occupancy
 _atom_site_disorder_assembly
 _atom_site_disorder_group
S1 S 0.81309(7) 0.65649(5) 0.30620(3) 0.02174(16) Uani 1 1 d . . . . .
F1 F 0.35471(16) 0.65226(14) 0.50404(6) 0.0307(3) Uani 1 1 d . . . . .
O1 O 1.06776(18) 1.28562(15) 0.43085(7) 0.0224(4) Uani 1 1 d . . . . .
O2 O 0.9727(2) 0.67742(15) 0.33593(8) 0.0261(4) Uani 1 1 d . . . . .
O3 O 0.7805(2) 0.54094(15) 0.26832(8) 0.0294(4) Uani 1 1 d . . . . .
O4 O 1.14151(18) 1.04764(15) 0.45570(7) 0.0238(4) Uani 1 1 d . . . . .
C1 C 0.4622(3) 0.6536(2) 0.45875(11) 0.0226(5) Uani 1 1 d . . . . .
C2 C 0.6085(3) 0.7133(2) 0.47275(11) 0.0236(5) Uani 1 1 d . . . . .
H14 H 0.6342 0.7532 0.5133 0.028 Uiso 1 1 calc R U . . .
C3 C 0.7179(3) 0.7139(2) 0.42611(11) 0.0221(5) Uani 1 1 d . . . . .
H15 H 0.8202 0.7545 0.4343 0.027 Uiso 1 1 calc R U . . .
C4 C 0.6772(3) 0.6548(2) 0.36741(10) 0.0194(5) Uani 1 1 d . . . . .
C5 C 0.7467(3) 0.7872(2) 0.25723(11) 0.0211(5) Uani 1 1 d . . . . .
H13 H 0.6816 0.7629 0.2197 0.025 Uiso 1 1 calc R U . . .
C6 C 0.7720(3) 0.9161(2) 0.26371(10) 0.0181(4) Uani 1 1 d . . . . .
C7 C 0.8647(3) 0.9979(2) 0.31122(10) 0.0166(4) Uani 1 1 d . . . . .
C8 C 0.8342(2) 1.1293(2) 0.29601(10) 0.0158(4) Uani 1 1 d . . . . .
C9 C 0.8991(2) 1.2295(2) 0.33431(10) 0.0170(4) Uani 1 1 d . . . . .
H7 H 0.8756 1.3180 0.3238 0.020 Uiso 1 1 calc R U . . .
C10 C 0.9991(2) 1.1978(2) 0.38840(10) 0.0179(4) Uani 1 1 d . . . . .
C11 C 1.0288(3) 1.4186(2) 0.41822(12) 0.0268(5) Uani 1 1 d . . . . .
H1 H 1.0607 1.4424 0.3757 0.040 Uiso 1 1 calc R U . . .
H5 H 1.0865 1.4738 0.4507 0.040 Uiso 1 1 calc R U . . .
H6 H 0.9122 1.4313 0.4196 0.040 Uiso 1 1 calc R U . . .
C12 C 0.4182(3) 0.5947(2) 0.40068(12) 0.0281(5) Uani 1 1 d . . . . .
H17 H 0.3150 0.5553 0.3926 0.034 Uiso 1 1 calc R U . . .
C13 C 0.5281(3) 0.5947(2) 0.35462(11) 0.0245(5) Uani 1 1 d . . . . .
H16 H 0.5020 0.5538 0.3144 0.029 Uiso 1 1 calc R U . . .
C14 C 0.6876(3) 1.0088(2) 0.21746(10) 0.0176(4) Uani 1 1 d . . . . .
C15 C 0.7256(2) 1.1365(2) 0.23694(10) 0.0170(4) Uani 1 1 d . . . . .
C16 C 0.9699(2) 0.9670(2) 0.36464(10) 0.0182(4) Uani 1 1 d . . . . .
H8 H 0.9951 0.8785 0.3746 0.022 Uiso 1 1 calc R U . . .
C17 C 1.0365(2) 1.0658(2) 0.40256(10) 0.0182(4) Uani 1 1 d . . . . .
C18 C 1.1893(3) 0.9168(2) 0.46932(12) 0.0288(5) Uani 1 1 d . . . . .
H2 H 1.0943 0.8648 0.4777 0.043 Uiso 1 1 calc R U . . .
H3 H 1.2669 0.9152 0.5072 0.043 Uiso 1 1 calc R U . . .
H4 H 1.2396 0.8803 0.4325 0.043 Uiso 1 1 calc R U . . .
C19 C 0.6616(3) 1.2424(2) 0.20261(10) 0.0198(5) Uani 1 1 d . . . . .
H12 H 0.6885 1.3291 0.2156 0.024 Uiso 1 1 calc R U . . .
C20 C 0.5571(3) 1.2188(2) 0.14874(11) 0.0234(5) Uani 1 1 d . . . . .
H11 H 0.5115 1.2901 0.1246 0.028 Uiso 1 1 calc R U . . .
C21 C 0.5184(3) 1.0914(2) 0.12965(10) 0.0259(5) Uani 1 1 d . . . . .
H9 H 0.4468 1.0772 0.0926 0.031 Uiso 1 1 calc R U . . .
C22 C 0.5824(3) 0.9856(2) 0.16380(10) 0.0221(5) Uani 1 1 d . . . . .
H10 H 0.5551 0.8991 0.1508 0.027 Uiso 1 1 calc R U . . .
 
 
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
 
loop_
 _geom_bond_atom_site_label_1
 _geom_bond_atom_site_label_2
 _geom_bond_distance
 _geom_bond_site_symmetry_2
 _geom_bond_publ_flag
S1 O2 1.4352(18) . ?
S1 O3 1.4386(16) . ?
S1 C5 1.749(2) . ?
S1 C4 1.774(2) . ?
F1 C1 1.353(3) . ?
O1 C10 1.357(3) . ?
O1 C11 1.421(3) . ?
O4 C17 1.370(2) . ?
O4 C18 1.421(3) . ?
C1 C2 1.372(3) . ?
C1 C12 1.379(3) . ?
C2 C3 1.386(3) . ?
C2 H14 0.9500 . ?
C3 C4 1.386(3) . ?
C3 H15 0.9500 . ?
C4 C13 1.390(3) . ?
C5 C6 1.343(3) . ?
C5 H13 0.9500 . ?
C6 C7 1.470(3) . ?
C6 C14 1.491(3) . ?
C7 C16 1.399(3) . ?
C7 C8 1.403(3) . ?
C8 C9 1.385(3) . ?
C8 C15 1.472(3) . ?
C9 C10 1.388(3) . ?
C9 H7 0.9500 . ?
C10 C17 1.415(3) . ?
C11 H1 0.9800 . ?
C11 H5 0.9800 . ?
C11 H6 0.9800 . ?
C12 C13 1.380(3) . ?
C12 H17 0.9500 . ?
C13 H16 0.9500 . ?
C14 C22 1.386(3) . ?
C14 C15 1.400(3) . ?
C15 C19 1.384(3) . ?
C16 C17 1.375(3) . ?
C16 H8 0.9500 . ?
C18 H2 0.9800 . ?
C18 H3 0.9800 . ?
C18 H4 0.9800 . ?
C19 C20 1.388(3) . ?
C19 H12 0.9500 . ?
C20 C21 1.395(3) . ?
C20 H11 0.9500 . ?
C21 C22 1.381(3) . ?
C21 H9 0.9500 . ?
C22 H10 0.9500 . ?
 
loop_
 _geom_angle_atom_site_label_1
 _geom_angle_atom_site_label_2
 _geom_angle_atom_site_label_3
 _geom_angle
 _geom_angle_site_symmetry_1
 _geom_angle_site_symmetry_3
 _geom_angle_publ_flag
O2 S1 O3 119.25(10) . . ?
O2 S1 C5 112.13(10) . . ?
O3 S1 C5 105.74(11) . . ?
O2 S1 C4 107.93(10) . . ?
O3 S1 C4 106.69(10) . . ?
C5 S1 C4 103.95(10) . . ?
C10 O1 C11 115.89(17) . . ?
C17 O4 C18 116.12(17) . . ?
F1 C1 C2 118.6(2) . . ?
F1 C1 C12 118.0(2) . . ?
C2 C1 C12 123.5(2) . . ?
C1 C2 C3 118.1(2) . . ?
C1 C2 H14 120.9 . . ?
C3 C2 H14 120.9 . . ?
C2 C3 C4 119.7(2) . . ?
C2 C3 H15 120.1 . . ?
C4 C3 H15 120.1 . . ?
C3 C4 C13 120.9(2) . . ?
C3 C4 S1 120.78(17) . . ?
C13 C4 S1 118.30(17) . . ?
C6 C5 S1 130.92(18) . . ?
C6 C5 H13 114.5 . . ?
S1 C5 H13 114.5 . . ?
C5 C6 C7 134.3(2) . . ?
C5 C6 C14 120.0(2) . . ?
C7 C6 C14 105.62(17) . . ?
C16 C7 C8 119.25(19) . . ?
C16 C7 C6 132.16(19) . . ?
C8 C7 C6 108.59(18) . . ?
C9 C8 C7 121.74(19) . . ?
C9 C8 C15 129.21(19) . . ?
C7 C8 C15 109.04(18) . . ?
C8 C9 C10 118.58(19) . . ?
C8 C9 H7 120.7 . . ?
C10 C9 H7 120.7 . . ?
O1 C10 C9 124.8(2) . . ?
O1 C10 C17 115.06(18) . . ?
C9 C10 C17 120.10(19) . . ?
O1 C11 H1 109.5 . . ?
O1 C11 H5 109.5 . . ?
H1 C11 H5 109.5 . . ?
O1 C11 H6 109.5 . . ?
H1 C11 H6 109.5 . . ?
H5 C11 H6 109.5 . . ?
C1 C12 C13 118.1(2) . . ?
C1 C12 H17 120.9 . . ?
C13 C12 H17 120.9 . . ?
C12 C13 C4 119.7(2) . . ?
C12 C13 H16 120.2 . . ?
C4 C13 H16 120.2 . . ?
C22 C14 C15 120.6(2) . . ?
C22 C14 C6 130.5(2) . . ?
C15 C14 C6 108.89(18) . . ?
C19 C15 C14 120.9(2) . . ?
C19 C15 C8 131.2(2) . . ?
C14 C15 C8 107.83(18) . . ?
C17 C16 C7 119.42(19) . . ?
C17 C16 H8 120.3 . . ?
C7 C16 H8 120.3 . . ?
O4 C17 C16 124.70(19) . . ?
O4 C17 C10 114.49(19) . . ?
C16 C17 C10 120.81(19) . . ?
O4 C18 H2 109.5 . . ?
O4 C18 H3 109.5 . . ?
H2 C18 H3 109.5 . . ?
O4 C18 H4 109.5 . . ?
H2 C18 H4 109.5 . . ?
H3 C18 H4 109.5 . . ?
C15 C19 C20 118.3(2) . . ?
C15 C19 H12 120.9 . . ?
C20 C19 H12 120.9 . . ?
C19 C20 C21 120.7(2) . . ?
C19 C20 H11 119.6 . . ?
C21 C20 H11 119.6 . . ?
C22 C21 C20 121.1(2) . . ?
C22 C21 H9 119.5 . . ?
C20 C21 H9 119.5 . . ?
C21 C22 C14 118.4(2) . . ?
C21 C22 H10 120.8 . . ?
C14 C22 H10 120.8 . . ?
 
_refine_diff_density_max    1.501
_refine_diff_density_min   -0.395
_refine_diff_density_rms    0.060

_shelxl_version_number 2014/6



 
data_180843LT_a
 
_audit_creation_method            SHELXL-2014/6
_chemical_name_systematic         ?
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C30 H28 O6 S2' 
_chemical_formula_weight          548.64

loop_
 _atom_type_symbol
 _atom_type_description
 _atom_type_scat_dispersion_real
 _atom_type_scat_dispersion_imag
 _atom_type_scat_source
 'C'  'C'   0.0033   0.0016
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'O'  'O'   0.0106   0.0060
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'S'  'S'   0.1246   0.1234
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'H'  'H'   0.0000   0.0000
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 
_space_group_crystal_system       monoclinic
_space_group_IT_number            14
_space_group_name_H-M_alt         'P 21/c'
_space_group_name_Hall            '-P 2ybc'
 
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
 
loop_
 _space_group_symop_operation_xyz
 'x, y, z'
 '-x, y+1/2, -z+1/2'
 '-x, -y, -z'
 'x, -y-1/2, z-1/2'
 
_cell_length_a                    20.676(2)
_cell_length_b                    14.0649(14)
_cell_length_c                    9.2725(8)
_cell_angle_alpha                 90
_cell_angle_beta                  101.965(4)
_cell_angle_gamma                 90
_cell_volume                      2637.9(4)
_cell_formula_units_Z             4
_cell_measurement_temperature     100(2)
_cell_measurement_reflns_used     6871
_cell_measurement_theta_min       2.4805
_cell_measurement_theta_max       26.2609
 
_exptl_crystal_description        tabullar
_exptl_crystal_colour             colorless
_exptl_crystal_density_meas       'not measured'
_exptl_crystal_density_method     'not measured'
_exptl_crystal_density_diffrn     1.381          
_exptl_crystal_F_000              1152
_exptl_transmission_factor_min    ?
_exptl_transmission_factor_max    ?
_exptl_crystal_size_max           0.16
_exptl_crystal_size_mid           0.13
_exptl_crystal_size_min           0.05
_exptl_absorpt_coefficient_mu     0.246
_shelx_estimated_absorpt_T_min    ?
_shelx_estimated_absorpt_T_max    ?
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.8369  
_exptl_absorpt_correction_T_max   0.9584
_exptl_absorpt_process_details    'SADABS V2014/4 (Bruker AXS Inc.)'
_exptl_absorpt_special_details    ?
_diffrn_ambient_temperature       100(2)
_diffrn_radiation_wavelength      0.71073
_diffrn_radiation_type            MoK\a
_diffrn_source                    ?
_diffrn_measurement_device_type   'Bruker APEX-II CCD'
_diffrn_measurement_method        'φ and ω scans'
_diffrn_detector_area_resol_mean  8.3333
_diffrn_reflns_number             18806
_diffrn_reflns_av_unetI/netI      0.0881
_diffrn_reflns_av_R_equivalents   0.0776
_diffrn_reflns_limit_h_min        -25
_diffrn_reflns_limit_h_max        25
_diffrn_reflns_limit_k_min        -17
_diffrn_reflns_limit_k_max        17
_diffrn_reflns_limit_l_min        -11
_diffrn_reflns_limit_l_max        9
_diffrn_reflns_theta_min          1.007
_diffrn_reflns_theta_max          26.485
_diffrn_reflns_theta_full         25.242
_diffrn_measured_fraction_theta_max   0.982
_diffrn_measured_fraction_theta_full  0.989
_diffrn_reflns_Laue_measured_fraction_max    0.982
_diffrn_reflns_Laue_measured_fraction_full   0.989
_diffrn_reflns_point_group_measured_fraction_max   0.982
_diffrn_reflns_point_group_measured_fraction_full  0.989
_reflns_number_total              5361
_reflns_number_gt                 3442
_reflns_threshold_expression      'I > 2σ(I)'
_reflns_Friedel_coverage          0.000
_reflns_Friedel_fraction_max      .
_reflns_Friedel_fraction_full     .
 
_reflns_special_details
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
 
_computing_data_collection        'Bruker APEX2'
_computing_cell_refinement        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction         'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution     ?
_computing_structure_refinement   'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics     'Bruker SHELXTL'
_computing_publication_material   'Bruker SHELXTL'
_refine_special_details           ?
_refine_ls_structure_factor_coef  Fsqd
_refine_ls_matrix_type            full
_refine_ls_weighting_scheme       calc
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1163P)²+7.4418P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary      ?
_atom_sites_solution_secondary    ?
_atom_sites_solution_hydrogens    geom
_refine_ls_hydrogen_treatment     constr
_refine_ls_extinction_method      none
_refine_ls_extinction_coef        .
_refine_ls_number_reflns          5361
_refine_ls_number_parameters      347
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.1252
_refine_ls_R_factor_gt            0.0982
_refine_ls_wR_factor_ref          0.2791
_refine_ls_wR_factor_gt           0.2655
_refine_ls_goodness_of_fit_ref    1.067
_refine_ls_restrained_S_all       1.067
_refine_ls_shift/su_max           0.000
_refine_ls_shift/su_mean          0.000
 
loop_
 _atom_site_label
 _atom_site_type_symbol
 _atom_site_fract_x
 _atom_site_fract_y
 _atom_site_fract_z
 _atom_site_U_iso_or_equiv
 _atom_site_adp_type
 _atom_site_occupancy
 _atom_site_site_symmetry_order  
 _atom_site_calc_flag
 _atom_site_refinement_flags_posn
 _atom_site_refinement_flags_adp
 _atom_site_refinement_flags_occupancy
 _atom_site_disorder_assembly
 _atom_site_disorder_group
C1 C 0.6192(3) 0.6054(4) 0.1104(5) 0.0429(14) Uani 1 1 d . . . . .
C2 C 0.5870(4) 0.6405(6) 0.2170(6) 0.063(2) Uani 1 1 d . . . . .
H2 H 0.5923 0.7050 0.2478 0.075 Uiso 1 1 calc R U . . .
C3 C 0.5475(4) 0.5805(7) 0.2769(7) 0.073(3) Uani 1 1 d . . . . .
H3 H 0.5260 0.6036 0.3511 0.088 Uiso 1 1 calc R U . . .
C4 C 0.5380(3) 0.4855(7) 0.2304(6) 0.062(2) Uani 1 1 d . . . . .
C5 C 0.5685(3) 0.4538(5) 0.1204(6) 0.0508(16) Uani 1 1 d . . . . .
H5 H 0.5612 0.3904 0.0856 0.061 Uiso 1 1 calc R U . . .
C6 C 0.6096(3) 0.5129(4) 0.0592(5) 0.0365(13) Uani 1 1 d . . . . .
H6 H 0.6306 0.4903 -0.0160 0.044 Uiso 1 1 calc R U . . .
C7 C 0.4982(4) 0.4165(8) 0.3007(9) 0.099(4) Uani 1 1 d . . . . .
H7A H 0.4792 0.3678 0.2287 0.149 Uiso 1 1 calc R U . . .
H7B H 0.4625 0.4507 0.3336 0.149 Uiso 1 1 calc R U . . .
H7C H 0.5269 0.3862 0.3856 0.149 Uiso 1 1 calc R U . . .
C8 C 0.7506(3) 0.6815(4) 0.1777(5) 0.0450(15) Uani 1 1 d . . . . .
H8A H 0.7809 0.7280 0.1464 0.054 Uiso 1 1 calc R U . . .
H8B H 0.7405 0.7049 0.2713 0.054 Uiso 1 1 calc R U . . .
C9 C 0.7871(3) 0.5857(4) 0.2081(5) 0.0359(13) Uani 1 1 d . . . . .
C10 C 0.8076(3) 0.5347(4) 0.0788(5) 0.0369(13) Uani 1 1 d . . . . .
C11 C 0.8398(3) 0.5714(5) -0.0248(6) 0.0501(17) Uani 1 1 d . . . . .
H11 H 0.8523 0.6365 -0.0226 0.060 Uiso 1 1 calc R U . . .
C12 C 0.8535(3) 0.5109(5) -0.1317(6) 0.0530(18) Uani 1 1 d . . . . .
H12 H 0.8754 0.5346 -0.2047 0.064 Uiso 1 1 calc R U . . .
C13 C 0.8355(3) 0.4165(5) -0.1336(6) 0.0480(16) Uani 1 1 d . . . . .
H13 H 0.8461 0.3759 -0.2072 0.058 Uiso 1 1 calc R U . . .
C14 C 0.8024(2) 0.3791(4) -0.0307(5) 0.0358(12) Uani 1 1 d . . . . .
H14 H 0.7902 0.3139 -0.0328 0.043 Uiso 1 1 calc R U . . .
C15 C 0.7878(2) 0.4404(4) 0.0755(5) 0.0292(11) Uani 1 1 d . . . . .
C16 C 0.7522(2) 0.4241(3) 0.1970(5) 0.0246(10) Uani 1 1 d . . . . .
C17 C 0.7211(2) 0.3432(3) 0.2339(5) 0.0240(10) Uani 1 1 d . . . . .
H17 H 0.7217 0.2857 0.1805 0.029 Uiso 1 1 calc R U . . .
C18 C 0.6887(2) 0.3486(3) 0.3522(5) 0.0243(10) Uani 1 1 d . . . . .
C19 C 0.6910(2) 0.4347(3) 0.4353(5) 0.0272(10) Uani 1 1 d . . . . .
C20 C 0.7218(2) 0.5141(3) 0.3943(5) 0.0273(11) Uani 1 1 d . . . . .
H20 H 0.7225 0.5721 0.4472 0.033 Uiso 1 1 calc R U . . .
C21 C 0.7517(2) 0.5074(4) 0.2738(5) 0.0283(11) Uani 1 1 d . . . . .
C22 C 0.6368(3) 0.1991(4) 0.3010(6) 0.0395(13) Uani 1 1 d . . . . .
H22A H 0.6180 0.2216 0.2011 0.059 Uiso 1 1 calc R U . . .
H22B H 0.6046 0.1585 0.3354 0.059 Uiso 1 1 calc R U . . .
H22C H 0.6771 0.1625 0.3002 0.059 Uiso 1 1 calc R U . . .
C23 C 0.6663(3) 0.5111(4) 0.6443(5) 0.0378(13) Uani 1 1 d . . . . .
H23A H 0.7134 0.5250 0.6795 0.057 Uiso 1 1 calc R U . . .
H23B H 0.6459 0.4980 0.7287 0.057 Uiso 1 1 calc R U . . .
H23C H 0.6445 0.5660 0.5897 0.057 Uiso 1 1 calc R U . . .
C24 C 0.9041(3) 0.5040(5) 0.3791(5) 0.0427(15) Uani 1 1 d . . . . .
C25 C 0.9499(3) 0.4788(6) 0.3005(6) 0.0535(18) Uani 1 1 d . . . . .
H25 H 0.9622 0.5218 0.2319 0.064 Uiso 1 1 calc R U . . .
C26 C 0.9787(3) 0.3890(6) 0.3216(7) 0.060(2) Uani 1 1 d . . . . .
H26 H 1.0110 0.3717 0.2670 0.073 Uiso 1 1 calc R U . . .
C27 C 0.9616(3) 0.3242(5) 0.4199(6) 0.0493(16) Uani 1 1 d . . . . .
C28 C 0.9143(3) 0.3532(5) 0.4999(6) 0.0470(15) Uani 1 1 d . . . . .
H28 H 0.9014 0.3105 0.5683 0.056 Uiso 1 1 calc R U . . .
C29 C 0.8864(3) 0.4416(5) 0.4811(5) 0.0404(14) Uani 1 1 d . . . . .
H29 H 0.8550 0.4604 0.5372 0.049 Uiso 1 1 calc R U . . .
C30 C 0.9908(3) 0.2260(6) 0.4391(7) 0.063(2) Uani 1 1 d . . . . .
H30A H 0.9938 0.2001 0.3426 0.094 Uiso 1 1 calc R U . . .
H30B H 0.9626 0.1849 0.4851 0.094 Uiso 1 1 calc R U . . .
H30C H 1.0351 0.2291 0.5022 0.094 Uiso 1 1 calc R U . . .
O1 O 0.6506(3) 0.7746(3) 0.0382(5) 0.086(2) Uani 1 1 d . . . . .
O2 O 0.6864(2) 0.6384(3) -0.0919(4) 0.0528(12) Uani 1 1 d . . . . .
O3 O 0.8427(2) 0.6463(3) 0.4777(4) 0.0502(11) Uani 1 1 d . . . . .
O4 O 0.65913(18) 0.4301(2) 0.5498(3) 0.0328(8) Uani 1 1 d . . . . .
O5 O 0.65244(19) 0.2783(2) 0.3971(4) 0.0368(9) Uani 1 1 d . . . . .
O6 O 0.9024(2) 0.6772(4) 0.2764(4) 0.0630(14) Uani 1 1 d . . . . .
S1 S 0.67523(10) 0.67954(10) 0.04114(13) 0.0503(5) Uani 1 1 d . . . . .
S2 S 0.86337(8) 0.61458(12) 0.34645(14) 0.0470(5) Uani 1 1 d . . . . .
 
 
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
 
loop_
 _geom_bond_atom_site_label_1
 _geom_bond_atom_site_label_2
 _geom_bond_distance
 _geom_bond_site_symmetry_2
 _geom_bond_publ_flag
C1 C6 1.385(8) . ?
C1 C2 1.392(9) . ?
C1 S1 1.775(7) . ?
C2 C3 1.369(12) . ?
C2 H2 0.9500 . ?
C3 C4 1.406(12) . ?
C3 H3 0.9500 . ?
C4 C5 1.379(9) . ?
C4 C7 1.506(11) . ?
C5 C6 1.391(8) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 C9 1.542(8) . ?
C8 S1 1.792(6) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C21 1.518(7) . ?
C9 C10 1.530(7) . ?
C9 S2 1.860(5) . ?
C10 C11 1.378(7) . ?
C10 C15 1.387(7) . ?
C11 C12 1.379(9) . ?
C11 H11 0.9500 . ?
C12 C13 1.379(9) . ?
C12 H12 0.9500 . ?
C13 C14 1.388(8) . ?
C13 H13 0.9500 . ?
C14 C15 1.389(7) . ?
C14 H14 0.9500 . ?
C15 C16 1.485(6) . ?
C16 C21 1.373(7) . ?
C16 C17 1.384(7) . ?
C17 C18 1.402(6) . ?
C17 H17 0.9500 . ?
C18 O5 1.356(6) . ?
C18 C19 1.432(6) . ?
C19 O4 1.362(6) . ?
C19 C20 1.378(7) . ?
C20 C21 1.387(6) . ?
C20 H20 0.9500 . ?
C22 O5 1.422(6) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 O4 1.425(6) . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 C25 1.357(9) . ?
C24 C29 1.394(8) . ?
C24 S2 1.764(7) . ?
C25 C26 1.391(10) . ?
C25 H25 0.9500 . ?
C26 C27 1.386(10) . ?
C26 H26 0.9500 . ?
C27 C28 1.406(8) . ?
C27 C30 1.502(10) . ?
C28 C29 1.366(9) . ?
C28 H28 0.9500 . ?
C29 H29 0.9500 . ?
C30 H30A 0.9800 . ?
C30 H30B 0.9800 . ?
C30 H30C 0.9800 . ?
O1 S1 1.430(5) . ?
O2 S1 1.424(4) . ?
O3 S2 1.442(4) . ?
O6 S2 1.437(4) . ?
 
loop_
 _geom_angle_atom_site_label_1
 _geom_angle_atom_site_label_2
 _geom_angle_atom_site_label_3
 _geom_angle
 _geom_angle_site_symmetry_1
 _geom_angle_site_symmetry_3
 _geom_angle_publ_flag
C6 C1 C2 121.4(7) . . ?
C6 C1 S1 119.1(4) . . ?
C2 C1 S1 119.5(5) . . ?
C3 C2 C1 118.9(7) . . ?
C3 C2 H2 120.6 . . ?
C1 C2 H2 120.6 . . ?
C2 C3 C4 121.2(6) . . ?
C2 C3 H3 119.4 . . ?
C4 C3 H3 119.4 . . ?
C5 C4 C3 118.6(7) . . ?
C5 C4 C7 119.1(8) . . ?
C3 C4 C7 122.3(7) . . ?
C4 C5 C6 121.3(7) . . ?
C4 C5 H5 119.3 . . ?
C6 C5 H5 119.3 . . ?
C1 C6 C5 118.5(6) . . ?
C1 C6 H6 120.7 . . ?
C5 C6 H6 120.7 . . ?
C4 C7 H7A 109.5 . . ?
C4 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C4 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C9 C8 S1 115.9(4) . . ?
C9 C8 H8A 108.3 . . ?
S1 C8 H8A 108.3 . . ?
C9 C8 H8B 108.3 . . ?
S1 C8 H8B 108.3 . . ?
H8A C8 H8B 107.4 . . ?
C21 C9 C10 102.1(4) . . ?
C21 C9 C8 116.7(5) . . ?
C10 C9 C8 118.1(4) . . ?
C21 C9 S2 107.0(3) . . ?
C10 C9 S2 108.0(4) . . ?
C8 C9 S2 104.4(3) . . ?
C11 C10 C15 121.7(5) . . ?
C11 C10 C9 128.6(5) . . ?
C15 C10 C9 109.7(4) . . ?
C10 C11 C12 118.1(6) . . ?
C10 C11 H11 121.0 . . ?
C12 C11 H11 121.0 . . ?
C13 C12 C11 120.6(5) . . ?
C13 C12 H12 119.7 . . ?
C11 C12 H12 119.7 . . ?
C12 C13 C14 121.8(5) . . ?
C12 C13 H13 119.1 . . ?
C14 C13 H13 119.1 . . ?
C13 C14 C15 117.6(6) . . ?
C13 C14 H14 121.2 . . ?
C15 C14 H14 121.2 . . ?
C10 C15 C14 120.2(5) . . ?
C10 C15 C16 108.7(4) . . ?
C14 C15 C16 131.1(5) . . ?
C21 C16 C17 121.3(4) . . ?
C21 C16 C15 108.7(4) . . ?
C17 C16 C15 130.0(4) . . ?
C16 C17 C18 118.1(4) . . ?
C16 C17 H17 120.9 . . ?
C18 C17 H17 120.9 . . ?
O5 C18 C17 125.8(4) . . ?
O5 C18 C19 114.2(4) . . ?
C17 C18 C19 120.0(4) . . ?
O4 C19 C20 125.4(4) . . ?
O4 C19 C18 114.3(4) . . ?
C20 C19 C18 120.2(4) . . ?
C19 C20 C21 118.4(4) . . ?
C19 C20 H20 120.8 . . ?
C21 C20 H20 120.8 . . ?
C16 C21 C20 121.9(5) . . ?
C16 C21 C9 110.8(4) . . ?
C20 C21 C9 127.3(4) . . ?
O5 C22 H22A 109.5 . . ?
O5 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
O5 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
O4 C23 H23A 109.5 . . ?
O4 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
O4 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C25 C24 C29 120.7(7) . . ?
C25 C24 S2 120.0(5) . . ?
C29 C24 S2 119.2(4) . . ?
C24 C25 C26 119.2(6) . . ?
C24 C25 H25 120.4 . . ?
C26 C25 H25 120.4 . . ?
C27 C26 C25 122.0(6) . . ?
C27 C26 H26 119.0 . . ?
C25 C26 H26 119.0 . . ?
C26 C27 C28 117.2(7) . . ?
C26 C27 C30 122.1(6) . . ?
C28 C27 C30 120.7(6) . . ?
C29 C28 C27 121.2(6) . . ?
C29 C28 H28 119.4 . . ?
C27 C28 H28 119.4 . . ?
C28 C29 C24 119.8(5) . . ?
C28 C29 H29 120.1 . . ?
C24 C29 H29 120.1 . . ?
C27 C30 H30A 109.5 . . ?
C27 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
C27 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
C19 O4 C23 115.8(4) . . ?
C18 O5 C22 116.5(4) . . ?
O2 S1 O1 119.0(3) . . ?
O2 S1 C1 108.1(3) . . ?
O1 S1 C1 107.4(4) . . ?
O2 S1 C8 110.2(3) . . ?
O1 S1 C8 104.7(3) . . ?
C1 S1 C8 106.9(3) . . ?
O6 S2 O3 119.0(3) . . ?
O6 S2 C24 108.9(3) . . ?
O3 S2 C24 110.0(3) . . ?
O6 S2 C9 107.3(2) . . ?
O3 S2 C9 107.0(3) . . ?
C24 S2 C9 103.4(2) . . ?
 
_refine_diff_density_max    0.397
_refine_diff_density_min   -0.375
_refine_diff_density_rms    0.094

_shelxl_version_number 2014/6



