 
data_t
 
_audit_creation_method            'SHELXL-2014/7'
_shelx_SHELXL_version_number      '2014/7'
_chemical_name_systematic         ?
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          'C20 H19 N O3 S'
_chemical_formula_sum
 'C20 H19 N O3 S' 
_chemical_formula_weight          353.42

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'
 'N'  'N'   0.0061   0.0033
 '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            15
_space_group_name_H-M_alt         'C 2/c'
_space_group_name_Hall            '-C 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+1/2, y+1/2, z'
 '-x+1/2, y+1/2, -z+1/2'
 '-x, -y, -z'
 'x, -y, z-1/2'
 '-x+1/2, -y+1/2, -z'
 'x+1/2, -y+1/2, z-1/2'
 
_cell_length_a                    24.575(7)
_cell_length_b                    5.6892(11)
_cell_length_c                    32.315(12)
_cell_angle_alpha                 90
_cell_angle_beta                  128.16(2)
_cell_angle_gamma                 90
_cell_volume                      3553(2)
_cell_formula_units_Z             8
_cell_measurement_temperature     294(2)
_cell_measurement_reflns_used     8723
_cell_measurement_theta_min       1.603
_cell_measurement_theta_max       25.495
 
_exptl_crystal_description        block
_exptl_crystal_colour             colorless
_exptl_crystal_density_meas       ?
_exptl_crystal_density_method     ?
_exptl_crystal_density_diffrn     1.322          
_exptl_crystal_F_000              1488
_exptl_transmission_factor_min    ?
_exptl_transmission_factor_max    ?
_exptl_crystal_size_max           0.150
_exptl_crystal_size_mid           0.120
_exptl_crystal_size_min           0.090
_exptl_absorpt_coefficient_mu     0.201
_shelx_estimated_absorpt_T_min    0.971
_shelx_estimated_absorpt_T_max    0.982
_exptl_absorpt_correction_type    'multi-scan'
_exptl_absorpt_correction_T_min   0.953
_exptl_absorpt_correction_T_max   0.995
_exptl_absorpt_process_details    'SADABS; Bruker, 2008'
_exptl_absorpt_special_details    ?
_diffrn_ambient_temperature       294(2)
_diffrn_radiation_wavelength      0.71073
_diffrn_radiation_type            MoK\a
_diffrn_source                    'fine-focus sealed tube'
_diffrn_measurement_device_type   'CCD area detector'
_diffrn_measurement_method        'phi and omega scans'
_diffrn_detector_area_resol_mean  ?
_diffrn_reflns_number             8723
_diffrn_reflns_av_unetI/netI      0.1220
_diffrn_reflns_av_R_equivalents   0.0914
_diffrn_reflns_limit_h_min        -29
_diffrn_reflns_limit_h_max        23
_diffrn_reflns_limit_k_min        -6
_diffrn_reflns_limit_k_max        6
_diffrn_reflns_limit_l_min        -35
_diffrn_reflns_limit_l_max        39
_diffrn_reflns_theta_min          1.603
_diffrn_reflns_theta_max          25.495
_diffrn_reflns_theta_full         25.242
_diffrn_measured_fraction_theta_max   0.998
_diffrn_measured_fraction_theta_full  0.998
_diffrn_reflns_Laue_measured_fraction_max    0.998
_diffrn_reflns_Laue_measured_fraction_full   0.998
_diffrn_reflns_point_group_measured_fraction_max   0.998
_diffrn_reflns_point_group_measured_fraction_full  0.998
_reflns_number_total              3292
_reflns_number_gt                 1659
_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        ?
_computing_cell_refinement        ?
_computing_data_reduction         ?
_computing_structure_solution     ?
_computing_structure_refinement 'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics     ?
_computing_publication_material   ?
_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)+(0.0305P)²] 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-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef        0.0027(4)
_refine_ls_extinction_expression
 'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
_refine_ls_number_reflns          3292
_refine_ls_number_parameters      227
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.1214
_refine_ls_R_factor_gt            0.0551
_refine_ls_wR_factor_ref          0.1485
_refine_ls_wR_factor_gt           0.1183
_refine_ls_goodness_of_fit_ref    0.969
_refine_ls_restrained_S_all       0.969
_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 0.09290(4) 0.10758(16) 0.59222(3) 0.0504(3) Uani 1 1 d . . . . .
N1 N 0.19374(16) 0.5762(6) 0.48373(11) 0.0598(8) Uani 1 1 d . . . . .
O1 O 0.08805(12) -0.1240(4) 0.57314(9) 0.0675(7) Uani 1 1 d . . . . .
O2 O 0.05034(12) 0.1682(5) 0.60678(9) 0.0714(8) Uani 1 1 d . . . . .
O3 O 0.20545(13) 0.7353(5) 0.52142(10) 0.0781(8) Uani 1 1 d . . . . .
H3A H 0.2394 0.8162 0.5319 0.117 Uiso 1 1 calc R U . . .
C1 C 0.17908(16) 0.1586(6) 0.64681(12) 0.0431(8) Uani 1 1 d . . . . .
C2 C 0.22869(18) 0.0037(6) 0.65868(13) 0.0474(9) Uani 1 1 d . . . . .
H2B H 0.2169 -0.1284 0.6377 0.057 Uiso 1 1 calc R U . . .
C3 C 0.29847(17) 0.0422(6) 0.70290(12) 0.0443(8) Uani 1 1 d . . . . .
C4 C 0.31508(17) 0.2423(6) 0.73355(13) 0.0480(9) Uani 1 1 d . . . . .
C5 C 0.26222(18) 0.4013(6) 0.71958(13) 0.0536(9) Uani 1 1 d . . . . .
H5A H 0.2732 0.5359 0.7397 0.064 Uiso 1 1 calc R U . . .
C6 C 0.19590(18) 0.3615(6) 0.67750(13) 0.0510(9) Uani 1 1 d . . . . .
H6A H 0.1615 0.4676 0.6688 0.061 Uiso 1 1 calc R U . . .
C7 C 0.35073(19) -0.1185(7) 0.71691(15) 0.0615(10) Uani 1 1 d . . . . .
H7A H 0.3399 -0.2532 0.6969 0.074 Uiso 1 1 calc R U . . .
C8 C 0.4168(2) -0.0771(8) 0.75959(16) 0.0762(12) Uani 1 1 d . . . . .
H8A H 0.4512 -0.1841 0.7687 0.091 Uiso 1 1 calc R U . . .
C9 C 0.4340(2) 0.1212(8) 0.78982(16) 0.0732(12) Uani 1 1 d . . . . .
H9A H 0.4799 0.1462 0.8189 0.088 Uiso 1 1 calc R U . . .
C10 C 0.3854(2) 0.2801(7) 0.77811(14) 0.0641(11) Uani 1 1 d . . . . .
H10A H 0.3978 0.4131 0.7989 0.077 Uiso 1 1 calc R U . . .
C11 C 0.12567(17) 0.2731(6) 0.42575(13) 0.0510(9) Uani 1 1 d . . . . .
C12 C 0.08279(18) 0.0841(7) 0.41337(14) 0.0556(10) Uani 1 1 d . . . . .
H12A H 0.0640 0.0668 0.4309 0.067 Uiso 1 1 calc R U . . .
C13 C 0.06704(19) -0.0781(7) 0.37634(15) 0.0635(11) Uani 1 1 d . . . . .
H13A H 0.0382 -0.2039 0.3691 0.076 Uiso 1 1 calc R U . . .
C14 C 0.0935(2) -0.0560(8) 0.35013(17) 0.0814(13) Uani 1 1 d . . . . .
H14A H 0.0833 -0.1674 0.3252 0.098 Uiso 1 1 calc R U . . .
C15 C 0.1354(3) 0.1312(9) 0.3605(2) 0.1029(17) Uani 1 1 d . . . . .
H15A H 0.1531 0.1480 0.3423 0.124 Uiso 1 1 calc R U . . .
C16 C 0.1512(2) 0.2937(8) 0.39790(17) 0.0848(14) Uani 1 1 d . . . . .
H16A H 0.1796 0.4202 0.4046 0.102 Uiso 1 1 calc R U . . .
C17 C 0.14147(18) 0.4439(6) 0.46563(13) 0.0509(9) Uani 1 1 d . . . . .
C18 C 0.09864(17) 0.4578(6) 0.48381(13) 0.0519(9) Uani 1 1 d . . . . .
H18A H 0.0512 0.4171 0.4547 0.062 Uiso 1 1 calc R U . . .
H18B H 0.0989 0.6186 0.4939 0.062 Uiso 1 1 calc R U . . .
C19 C 0.12390(17) 0.2963(6) 0.53020(13) 0.0515(9) Uani 1 1 d . . . . .
H19A H 0.1259 0.1359 0.5210 0.062 Uiso 1 1 calc R U . . .
H19B H 0.1702 0.3423 0.5602 0.062 Uiso 1 1 calc R U . . .
C20 C 0.07621(16) 0.3084(6) 0.54471(12) 0.0459(8) Uani 1 1 d . . . . .
H20A H 0.0292 0.2842 0.5130 0.055 Uiso 1 1 calc R U . . .
H20B H 0.0787 0.4657 0.5574 0.055 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 O1 1.428(2) . ?
S1 O2 1.429(2) . ?
S1 C20 1.747(3) . ?
S1 C1 1.751(3) . ?
N1 C17 1.277(4) . ?
N1 O3 1.398(3) . ?
O3 H3A 0.8200 . ?
C1 C2 1.354(4) . ?
C1 C6 1.407(4) . ?
C2 C3 1.415(4) . ?
C2 H2B 0.9300 . ?
C3 C4 1.394(4) . ?
C3 C7 1.404(4) . ?
C4 C5 1.409(4) . ?
C4 C10 1.426(5) . ?
C5 C6 1.348(4) . ?
C5 H5A 0.9300 . ?
C6 H6A 0.9300 . ?
C7 C8 1.352(5) . ?
C7 H7A 0.9300 . ?
C8 C9 1.377(5) . ?
C8 H8A 0.9300 . ?
C9 C10 1.352(5) . ?
C9 H9A 0.9300 . ?
C10 H10A 0.9300 . ?
C11 C12 1.380(5) . ?
C11 C16 1.384(4) . ?
C11 C17 1.462(5) . ?
C12 C13 1.364(4) . ?
C12 H12A 0.9300 . ?
C13 C14 1.355(5) . ?
C13 H13A 0.9300 . ?
C14 C15 1.371(5) . ?
C14 H14A 0.9300 . ?
C15 C16 1.373(5) . ?
C15 H15A 0.9300 . ?
C16 H16A 0.9300 . ?
C17 C18 1.491(4) . ?
C18 C19 1.526(4) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 C20 1.509(4) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
 
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
O1 S1 O2 118.82(16) . . ?
O1 S1 C20 108.18(15) . . ?
O2 S1 C20 108.02(16) . . ?
O1 S1 C1 108.32(16) . . ?
O2 S1 C1 107.71(15) . . ?
C20 S1 C1 104.95(15) . . ?
C17 N1 O3 112.8(3) . . ?
N1 O3 H3A 109.5 . . ?
C2 C1 C6 120.9(3) . . ?
C2 C1 S1 119.6(3) . . ?
C6 C1 S1 119.5(3) . . ?
C1 C2 C3 120.2(3) . . ?
C1 C2 H2B 119.9 . . ?
C3 C2 H2B 119.9 . . ?
C4 C3 C7 119.7(3) . . ?
C4 C3 C2 118.9(3) . . ?
C7 C3 C2 121.4(3) . . ?
C3 C4 C5 119.3(3) . . ?
C3 C4 C10 118.7(3) . . ?
C5 C4 C10 122.0(3) . . ?
C6 C5 C4 121.1(3) . . ?
C6 C5 H5A 119.5 . . ?
C4 C5 H5A 119.5 . . ?
C5 C6 C1 119.6(3) . . ?
C5 C6 H6A 120.2 . . ?
C1 C6 H6A 120.2 . . ?
C8 C7 C3 119.9(4) . . ?
C8 C7 H7A 120.0 . . ?
C3 C7 H7A 120.0 . . ?
C7 C8 C9 120.9(4) . . ?
C7 C8 H8A 119.5 . . ?
C9 C8 H8A 119.5 . . ?
C10 C9 C8 121.3(4) . . ?
C10 C9 H9A 119.3 . . ?
C8 C9 H9A 119.3 . . ?
C9 C10 C4 119.4(4) . . ?
C9 C10 H10A 120.3 . . ?
C4 C10 H10A 120.3 . . ?
C12 C11 C16 116.7(3) . . ?
C12 C11 C17 120.9(3) . . ?
C16 C11 C17 122.4(3) . . ?
C13 C12 C11 122.2(3) . . ?
C13 C12 H12A 118.9 . . ?
C11 C12 H12A 118.9 . . ?
C14 C13 C12 120.0(4) . . ?
C14 C13 H13A 120.0 . . ?
C12 C13 H13A 120.0 . . ?
C13 C14 C15 119.8(4) . . ?
C13 C14 H14A 120.1 . . ?
C15 C14 H14A 120.1 . . ?
C14 C15 C16 120.0(4) . . ?
C14 C15 H15A 120.0 . . ?
C16 C15 H15A 120.0 . . ?
C15 C16 C11 121.3(4) . . ?
C15 C16 H16A 119.4 . . ?
C11 C16 H16A 119.4 . . ?
N1 C17 C11 116.1(3) . . ?
N1 C17 C18 122.9(3) . . ?
C11 C17 C18 121.0(3) . . ?
C17 C18 C19 113.4(3) . . ?
C17 C18 H18A 108.9 . . ?
C19 C18 H18A 108.9 . . ?
C17 C18 H18B 108.9 . . ?
C19 C18 H18B 108.9 . . ?
H18A C18 H18B 107.7 . . ?
C20 C19 C18 110.8(3) . . ?
C20 C19 H19A 109.5 . . ?
C18 C19 H19A 109.5 . . ?
C20 C19 H19B 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 108.1 . . ?
C19 C20 S1 115.9(2) . . ?
C19 C20 H20A 108.3 . . ?
S1 C20 H20A 108.3 . . ?
C19 C20 H20B 108.3 . . ?
S1 C20 H20B 108.3 . . ?
H20A C20 H20B 107.4 . . ?
 
_refine_diff_density_max    0.199
_refine_diff_density_min   -0.228
_refine_diff_density_rms    0.050



