 
data_cu_mh236_0m_a
 
_audit_creation_method            'SHELXL-2017/1'
_shelx_SHELXL_version_number      '2017/1'
_chemical_name_systematic         ?
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C43 H33 Cl3 O4 S2' 
_chemical_formula_weight          784.16

loop_
 _atom_type_symbol
 _atom_type_description
 _atom_type_scat_dispersion_real
 _atom_type_scat_dispersion_imag
 _atom_type_scat_source
 'C'  'C'   0.0181   0.0091
 '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'   0.0492   0.0322
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'S'  'S'   0.3331   0.5567
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'Cl'  'Cl'   0.3639   0.7018
 '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                    8.1459(3)
_cell_length_b                    9.0608(4)
_cell_length_c                    13.5621(5)
_cell_angle_alpha                 75.860(2)
_cell_angle_beta                  73.582(2)
_cell_angle_gamma                 84.176(2)
_cell_volume                      930.52(6)
_cell_formula_units_Z             1
_cell_measurement_temperature     173(2)
_cell_measurement_reflns_used     5252
_cell_measurement_theta_min       5.04
_cell_measurement_theta_max       66.53
 
_exptl_crystal_description        'prizm'
_exptl_crystal_colour             'red'
_exptl_crystal_density_meas       ?
_exptl_crystal_density_method     ?
_exptl_crystal_density_diffrn     1.399          
_exptl_crystal_F_000              406
_exptl_transmission_factor_min    ?
_exptl_transmission_factor_max    ?
_exptl_crystal_size_max           0.090
_exptl_crystal_size_mid           0.080
_exptl_crystal_size_min           0.030
_exptl_absorpt_coefficient_mu     3.628
_shelx_estimated_absorpt_T_min    0.736
_shelx_estimated_absorpt_T_max    0.899
_exptl_absorpt_correction_type    'multi-scan'
_exptl_absorpt_correction_T_min   0.6741
_exptl_absorpt_correction_T_max   0.7528
_exptl_absorpt_process_details    ?SADABS
_exptl_absorpt_special_details    ?
_diffrn_ambient_temperature       173(2)
_diffrn_radiation_wavelength      1.54178
_diffrn_radiation_type            CuK\a
_diffrn_source                    'Incoatec I\mS'
_diffrn_measurement_device_type   'Bruker Apex II CCD'
_diffrn_measurement_method        'φ and ω scans'
_diffrn_detector_area_resol_mean  ?
_diffrn_reflns_number             8785
_diffrn_reflns_av_unetI/netI      0.0408
_diffrn_reflns_av_R_equivalents   0.0463
_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        -16
_diffrn_reflns_limit_l_max        16
_diffrn_reflns_theta_min          3.487
_diffrn_reflns_theta_max          66.525
_diffrn_reflns_theta_full         66.525
_diffrn_measured_fraction_theta_max   0.985
_diffrn_measured_fraction_theta_full  0.985
_diffrn_reflns_Laue_measured_fraction_max    0.985
_diffrn_reflns_Laue_measured_fraction_full   0.985
_diffrn_reflns_point_group_measured_fraction_max   0.985
_diffrn_reflns_point_group_measured_fraction_full  0.985
_reflns_number_total              3229
_reflns_number_gt                 3005
_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        'Bruker SAINT'
_computing_data_reduction         'Bruker SAINT'
_computing_structure_solution     'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement 'SHELXL-2014/7 (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)+(0.0563P)²+1.4494P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary      ?
_atom_sites_solution_secondary    ?
_atom_sites_solution_hydrogens    geom
_refine_ls_hydrogen_treatment     mixed
_refine_ls_extinction_method      none
_refine_ls_extinction_coef        .
_refine_ls_number_reflns          3229
_refine_ls_number_parameters      255
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0566
_refine_ls_R_factor_gt            0.0530
_refine_ls_wR_factor_ref          0.1411
_refine_ls_wR_factor_gt           0.1387
_refine_ls_goodness_of_fit_ref    1.077
_refine_ls_restrained_S_all       1.077
_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 0.59212(8) 0.46334(7) 0.67777(5) 0.0212(2) Uani 1 1 d . . . . .
O1 O 0.4256(2) 0.5035(3) 0.66114(15) 0.0328(5) Uani 1 1 d . . . . .
O2 O 0.6518(3) 0.3078(2) 0.68425(16) 0.0327(5) Uani 1 1 d . . . . .
C1 C 0.4178(3) 0.3948(3) 0.9646(2) 0.0200(5) Uani 1 1 d . . . . .
H1B H 0.364836 0.327280 0.940321 0.024 Uiso 1 1 calc R U . . .
C2 C 0.5414(3) 0.4982(3) 0.89392(19) 0.0193(5) Uani 1 1 d . . . . .
C3 C 0.6217(3) 0.6032(3) 0.9306(2) 0.0200(5) Uani 1 1 d . . . . .
C4 C 0.7420(3) 0.6941(3) 0.83965(19) 0.0196(5) Uani 1 1 d . . . . .
C5 C 0.7361(3) 0.6439(3) 0.7529(2) 0.0210(5) Uani 1 1 d . . . . .
C6 C 0.6130(3) 0.5266(3) 0.7859(2) 0.0204(5) Uani 1 1 d . . . . .
C7 C 0.8151(3) 0.6773(3) 0.63902(19) 0.0197(5) Uani 1 1 d . . . . .
C8 C 0.7487(3) 0.5901(3) 0.5876(2) 0.0207(5) Uani 1 1 d . . . . .
C9 C 0.8016(3) 0.6020(3) 0.4800(2) 0.0256(6) Uani 1 1 d . . . . .
H9A H 0.753075 0.542520 0.447288 0.031 Uiso 1 1 calc R U . . .
C10 C 0.9279(4) 0.7039(3) 0.4216(2) 0.0300(6) Uani 1 1 d . . . . .
H10A H 0.967332 0.714968 0.347332 0.036 Uiso 1 1 calc R U . . .
C11 C 0.9981(4) 0.7905(3) 0.4705(2) 0.0286(6) Uani 1 1 d . . . . .
H11A H 1.085752 0.858904 0.428943 0.034 Uiso 1 1 calc R U . . .
C12 C 0.9426(3) 0.7790(3) 0.5785(2) 0.0253(6) Uani 1 1 d . . . . .
H12A H 0.990696 0.839420 0.610794 0.030 Uiso 1 1 calc R U . . .
C13 C 0.8391(3) 0.8200(3) 0.84551(18) 0.0189(5) Uani 1 1 d . . . . .
C14 C 0.7542(3) 0.9602(3) 0.8561(2) 0.0215(5) Uani 1 1 d . . . . .
C15 C 0.8461(4) 1.0776(3) 0.8622(2) 0.0252(6) Uani 1 1 d . . . . .
H15A H 0.788739 1.172689 0.869162 0.030 Uiso 1 1 calc R U . . .
C16 C 1.0184(4) 1.0600(3) 0.8584(2) 0.0274(6) Uani 1 1 d . . . . .
C17 C 1.0995(3) 0.9198(3) 0.8490(2) 0.0303(6) Uani 1 1 d . . . . .
H17A H 1.217272 0.905633 0.847360 0.036 Uiso 1 1 calc R U . . .
C18 C 1.0133(3) 0.7996(3) 0.8419(2) 0.0255(6) Uani 1 1 d . . . . .
C19 C 0.5671(4) 0.9855(3) 0.8588(3) 0.0335(7) Uani 1 1 d . . . . .
H19A H 0.5494(8) 0.961(3) 0.8006(16) 0.050 Uiso 1 1 calc R U . . .
H19B H 0.5354(11) 1.086(2) 0.8583(19) 0.050 Uiso 1 1 calc R U . . .
H19C H 0.5023(15) 0.925(2) 0.9192(16) 0.050 Uiso 1 1 calc R U . . .
C20 C 1.1164(4) 1.1885(4) 0.8656(3) 0.0393(8) Uani 1 1 d . . . . .
H20A H 1.235779 1.154580 0.861535 0.059 Uiso 1 1 calc R U . . .
H20B H 1.112452 1.276010 0.807189 0.059 Uiso 1 1 calc R U . . .
H20C H 1.064382 1.218046 0.932858 0.059 Uiso 1 1 calc R U . . .
C21 C 1.1057(4) 0.6486(4) 0.8323(3) 0.0459(9) Uani 1 1 d . . . . .
H21A H 1.026266 0.577477 0.828185 0.069 Uiso 1 1 calc R U . . .
H21B H 1.201512 0.663155 0.768391 0.069 Uiso 1 1 calc R U . . .
H21C H 1.149468 0.607071 0.894217 0.069 Uiso 1 1 calc R U . . .
Cl1S Cl 0.6117(3) 0.0440(3) 0.37724(15) 0.0719(6) Uani 0.5 1 d . . P A -1
Cl2S Cl 0.3987(3) -0.1537(2) 0.5600(2) 0.0632(6) Uani 0.5 1 d . . P A -1
Cl3S Cl 0.5300(3) 0.1183(2) 0.57846(15) 0.0551(5) Uani 0.5 1 d . . P A -1
C1S C 0.4541(9) 0.0348(7) 0.4980(5) 0.0377(15) Uani 0.5 1 d . . P A -1
H1SA H 0.349571 0.093953 0.483586 0.045 Uiso 0.5 1 calc R U P A -1
 
 
_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 1.434(2) . ?
S1 O1 1.434(2) . ?
S1 C6 1.754(3) . ?
S1 C8 1.781(3) . ?
C1 C3 1.370(4) 2_667 ?
C1 C2 1.420(3) . ?
C1 H1B 0.9500 . ?
C2 C6 1.384(4) . ?
C2 C3 1.457(3) . ?
C3 C4 1.464(3) . ?
C4 C5 1.375(4) . ?
C4 C13 1.482(3) . ?
C5 C6 1.438(4) . ?
C5 C7 1.463(3) . ?
C7 C12 1.394(4) . ?
C7 C8 1.404(4) . ?
C8 C9 1.380(4) . ?
C9 C10 1.384(4) . ?
C9 H9A 0.9500 . ?
C10 C11 1.393(4) . ?
C10 H10A 0.9500 . ?
C11 C12 1.386(4) . ?
C11 H11A 0.9500 . ?
C12 H12A 0.9500 . ?
C13 C18 1.401(4) . ?
C13 C14 1.403(4) . ?
C14 C15 1.391(4) . ?
C14 C19 1.510(4) . ?
C15 C16 1.385(4) . ?
C15 H15A 0.9500 . ?
C16 C17 1.388(4) . ?
C16 C20 1.513(4) . ?
C17 C18 1.390(4) . ?
C17 H17A 0.9500 . ?
C18 C21 1.510(4) . ?
C19 H19A 0.920(19) . ?
C19 H19B 0.920(19) . ?
C19 H19C 0.92(2) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
Cl1S C1S 1.762(7) . ?
Cl2S C1S 1.752(7) . ?
Cl3S C1S 1.740(7) . ?
C1S H1SA 1.0000 . ?
 
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 O1 117.82(13) . . ?
O2 S1 C6 110.45(12) . . ?
O1 S1 C6 110.96(12) . . ?
O2 S1 C8 111.19(12) . . ?
O1 S1 C8 111.40(12) . . ?
C6 S1 C8 92.10(12) . . ?
C3 C1 C2 117.1(2) 2_667 . ?
C3 C1 H1B 121.4 2_667 . ?
C2 C1 H1B 121.4 . . ?
C6 C2 C1 133.2(2) . . ?
C6 C2 C3 105.1(2) . . ?
C1 C2 C3 121.7(2) . . ?
C1 C3 C2 121.2(2) 2_667 . ?
C1 C3 C4 130.1(2) 2_667 . ?
C2 C3 C4 108.7(2) . . ?
C5 C4 C3 106.5(2) . . ?
C5 C4 C13 129.4(2) . . ?
C3 C4 C13 124.0(2) . . ?
C4 C5 C6 108.9(2) . . ?
C4 C5 C7 138.6(2) . . ?
C6 C5 C7 112.5(2) . . ?
C2 C6 C5 110.8(2) . . ?
C2 C6 S1 138.0(2) . . ?
C5 C6 S1 111.22(19) . . ?
C12 C7 C8 118.3(2) . . ?
C12 C7 C5 129.4(2) . . ?
C8 C7 C5 112.2(2) . . ?
C9 C8 C7 123.2(2) . . ?
C9 C8 S1 124.9(2) . . ?
C7 C8 S1 111.93(19) . . ?
C8 C9 C10 117.4(3) . . ?
C8 C9 H9A 121.3 . . ?
C10 C9 H9A 121.3 . . ?
C9 C10 C11 120.8(2) . . ?
C9 C10 H10A 119.6 . . ?
C11 C10 H10A 119.6 . . ?
C12 C11 C10 121.3(3) . . ?
C12 C11 H11A 119.3 . . ?
C10 C11 H11A 119.3 . . ?
C11 C12 C7 119.0(3) . . ?
C11 C12 H12A 120.5 . . ?
C7 C12 H12A 120.5 . . ?
C18 C13 C14 119.9(2) . . ?
C18 C13 C4 120.7(2) . . ?
C14 C13 C4 119.3(2) . . ?
C15 C14 C13 119.0(2) . . ?
C15 C14 C19 120.1(2) . . ?
C13 C14 C19 120.9(2) . . ?
C16 C15 C14 122.0(3) . . ?
C16 C15 H15A 119.0 . . ?
C14 C15 H15A 119.0 . . ?
C15 C16 C17 118.1(2) . . ?
C15 C16 C20 121.4(3) . . ?
C17 C16 C20 120.5(3) . . ?
C16 C17 C18 122.0(3) . . ?
C16 C17 H17A 119.0 . . ?
C18 C17 H17A 119.0 . . ?
C17 C18 C13 119.0(3) . . ?
C17 C18 C21 120.4(3) . . ?
C13 C18 C21 120.6(3) . . ?
C14 C19 H19A 109.5 . . ?
C14 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C14 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C16 C20 H20A 109.5 . . ?
C16 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C16 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C18 C21 H21A 109.5 . . ?
C18 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C18 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
Cl3S C1S Cl2S 110.9(4) . . ?
Cl3S C1S Cl1S 109.0(4) . . ?
Cl2S C1S Cl1S 111.1(4) . . ?
Cl3S C1S H1SA 108.6 . . ?
Cl2S C1S H1SA 108.6 . . ?
Cl1S C1S H1SA 108.6 . . ?
 
loop_
 _geom_torsion_atom_site_label_1
 _geom_torsion_atom_site_label_2
 _geom_torsion_atom_site_label_3
 _geom_torsion_atom_site_label_4
 _geom_torsion
 _geom_torsion_site_symmetry_1
 _geom_torsion_site_symmetry_2
 _geom_torsion_site_symmetry_3
 _geom_torsion_site_symmetry_4
 _geom_torsion_publ_flag
C3 C1 C2 C6 179.1(3) 2_667 . . . ?
C3 C1 C2 C3 -0.7(4) 2_667 . . . ?
C6 C2 C3 C1 -179.1(2) . . . 2_667 ?
C1 C2 C3 C1 0.7(4) . . . 2_667 ?
C6 C2 C3 C4 0.3(3) . . . . ?
C1 C2 C3 C4 -179.9(2) . . . . ?
C1 C3 C4 C5 178.3(3) 2_667 . . . ?
C2 C3 C4 C5 -1.0(3) . . . . ?
C1 C3 C4 C13 -4.8(4) 2_667 . . . ?
C2 C3 C4 C13 175.8(2) . . . . ?
C3 C4 C5 C6 1.3(3) . . . . ?
C13 C4 C5 C6 -175.3(3) . . . . ?
C3 C4 C5 C7 179.7(3) . . . . ?
C13 C4 C5 C7 3.1(5) . . . . ?
C1 C2 C6 C5 -179.3(3) . . . . ?
C3 C2 C6 C5 0.5(3) . . . . ?
C1 C2 C6 S1 2.8(5) . . . . ?
C3 C2 C6 S1 -177.4(2) . . . . ?
C4 C5 C6 C2 -1.2(3) . . . . ?
C7 C5 C6 C2 179.9(2) . . . . ?
C4 C5 C6 S1 177.33(18) . . . . ?
C7 C5 C6 S1 -1.5(3) . . . . ?
O2 S1 C6 C2 -67.8(3) . . . . ?
O1 S1 C6 C2 64.8(3) . . . . ?
C8 S1 C6 C2 178.7(3) . . . . ?
O2 S1 C6 C5 114.3(2) . . . . ?
O1 S1 C6 C5 -113.2(2) . . . . ?
C8 S1 C6 C5 0.7(2) . . . . ?
C4 C5 C7 C12 3.9(5) . . . . ?
C6 C5 C7 C12 -177.7(3) . . . . ?
C4 C5 C7 C8 -176.6(3) . . . . ?
C6 C5 C7 C8 1.8(3) . . . . ?
C12 C7 C8 C9 -1.0(4) . . . . ?
C5 C7 C8 C9 179.4(2) . . . . ?
C12 C7 C8 S1 178.35(19) . . . . ?
C5 C7 C8 S1 -1.2(3) . . . . ?
O2 S1 C8 C9 66.8(3) . . . . ?
O1 S1 C8 C9 -66.8(3) . . . . ?
C6 S1 C8 C9 179.7(2) . . . . ?
O2 S1 C8 C7 -112.6(2) . . . . ?
O1 S1 C8 C7 113.8(2) . . . . ?
C6 S1 C8 C7 0.3(2) . . . . ?
C7 C8 C9 C10 0.9(4) . . . . ?
S1 C8 C9 C10 -178.4(2) . . . . ?
C8 C9 C10 C11 0.0(4) . . . . ?
C9 C10 C11 C12 -0.8(4) . . . . ?
C10 C11 C12 C7 0.6(4) . . . . ?
C8 C7 C12 C11 0.2(4) . . . . ?
C5 C7 C12 C11 179.7(3) . . . . ?
C5 C4 C13 C18 -80.0(4) . . . . ?
C3 C4 C13 C18 103.9(3) . . . . ?
C5 C4 C13 C14 100.8(3) . . . . ?
C3 C4 C13 C14 -75.3(3) . . . . ?
C18 C13 C14 C15 0.4(4) . . . . ?
C4 C13 C14 C15 179.6(2) . . . . ?
C18 C13 C14 C19 179.2(2) . . . . ?
C4 C13 C14 C19 -1.6(4) . . . . ?
C13 C14 C15 C16 -0.2(4) . . . . ?
C19 C14 C15 C16 -179.0(2) . . . . ?
C14 C15 C16 C17 -0.4(4) . . . . ?
C14 C15 C16 C20 -179.7(3) . . . . ?
C15 C16 C17 C18 0.9(4) . . . . ?
C20 C16 C17 C18 -179.8(3) . . . . ?
C16 C17 C18 C13 -0.8(4) . . . . ?
C16 C17 C18 C21 -179.6(3) . . . . ?
C14 C13 C18 C17 0.1(4) . . . . ?
C4 C13 C18 C17 -179.2(2) . . . . ?
C14 C13 C18 C21 178.9(3) . . . . ?
C4 C13 C18 C21 -0.3(4) . . . . ?
 
loop_
 _geom_hbond_atom_site_label_D 
 _geom_hbond_atom_site_label_H 
 _geom_hbond_atom_site_label_A 
 _geom_hbond_distance_DH 
 _geom_hbond_distance_HA 
 _geom_hbond_distance_DA 
 _geom_hbond_angle_DHA 
 _geom_hbond_site_symmetry_A 
 _geom_hbond_publ_flag
C9 H9A O1  0.95 2.47 3.355(3) 155.6 2_666 yes
 
_refine_diff_density_max    0.662
_refine_diff_density_min   -0.451
_refine_diff_density_rms    0.068



