 
data_shs-2-20180919 
 
_audit_creation_method            SHELXL-97 
_chemical_name_systematic 
; 
 ? 
; 
_chemical_name_common             ? 
_chemical_melting_point           ? 
_chemical_formula_moiety          ? 
_chemical_formula_sum 
 'C21 H19 N O S' 
_chemical_formula_weight          333.43 
 
loop_ 
 _atom_type_symbol 
 _atom_type_description 
 _atom_type_scat_dispersion_real 
 _atom_type_scat_dispersion_imag 
 _atom_type_scat_source 
 'C'  'C'   0.0181   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' 
 'N'  'N'   0.0311   0.0180 
 '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' 
 
_symmetry_cell_setting            monoclinic
 
_symmetry_space_group_name_H-M    Cc 
 
loop_ 
 _symmetry_equiv_pos_as_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' 
 
_cell_length_a                    28.9068(5) 
_cell_length_b                    5.75310(10) 
_cell_length_c                    10.5484(2) 
_cell_angle_alpha                 90.00 
_cell_angle_beta                  98.531(2) 
_cell_angle_gamma                 90.00 
_cell_volume                      1734.83(5) 
_cell_formula_units_Z             4 
_cell_measurement_temperature     293(2) 
_cell_measurement_reflns_used   4183
_cell_measurement_theta_min     6.1530
_cell_measurement_theta_max     70.9360 
 
_exptl_crystal_description        block 
_exptl_crystal_colour             colorless 
_exptl_crystal_size_max           0.20 
_exptl_crystal_size_mid           0.20 
_exptl_crystal_size_min           0.20 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_diffrn     1.277 
_exptl_crystal_density_method     'not measured' 
_exptl_crystal_F_000              704 
_exptl_absorpt_coefficient_mu     1.694 
_exptl_absorpt_correction_type    multi-scan 
_exptl_absorpt_correction_T_min                   0.73520
_exptl_absorpt_correction_T_max                   1.00000 
_exptl_absorpt_process_details   sadabs   
 
_exptl_special_details 
; 
 ? 
; 
 
_diffrn_ambient_temperature       293(2) 
_diffrn_radiation_wavelength      1.54184 
_diffrn_radiation_type            CuK\a 
_diffrn_radiation_source          'fine-focus sealed tube' 
_diffrn_radiation_monochromator   graphite 
_diffrn_measurement_device_type   'SuperNova, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method        'ω scans' 
_diffrn_detector_area_resol_mean  ? 
_diffrn_standards_number          0 
_diffrn_standards_interval_count  0 
_diffrn_standards_interval_time   0 
_diffrn_standards_decay_%         0 
_diffrn_reflns_number             5226 
_diffrn_reflns_av_R_equivalents   0.0166 
_diffrn_reflns_av_sigmaI/netI     0.0223 
_diffrn_reflns_limit_h_min        -34 
_diffrn_reflns_limit_h_max        35 
_diffrn_reflns_limit_k_min        -5 
_diffrn_reflns_limit_k_max        6 
_diffrn_reflns_limit_l_min        -12 
_diffrn_reflns_limit_l_max        9 
_diffrn_reflns_theta_min          6.19 
_diffrn_reflns_theta_max          71.18 
_reflns_number_total              2646 
_reflns_number_gt                 2575 
_reflns_threshold_expression      I>2sigma(I) 
 
_computing_data_collection         'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)' 
_computing_cell_refinement         'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction          'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_structure_solution     'SHELXS-97 (Sheldrick, 1990)' 
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 1997)' 
_computing_molecular_graphics     'Olex2 (Dolomanov et al., 2009)'
 
_computing_publication_material   'Olex2 (Dolomanov et al., 2009)' 
 
_refine_special_details 
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
; 
 
_refine_ls_structure_factor_coef  Fsqd  
_refine_ls_matrix_type            full 
_refine_ls_weighting_scheme       calc  
_refine_ls_weighting_details 
 'calc w=1/[σ²(Fo²)+(0.0783P)²+0.0224P] where P=(Fo²+2Fc²)/3' 
_atom_sites_solution_primary      direct 
_atom_sites_solution_secondary    difmap 
_atom_sites_solution_hydrogens    geom 
_refine_ls_hydrogen_treatment     mixed 
_refine_ls_extinction_method      none 
_refine_ls_extinction_coef        ? 
_refine_ls_abs_structure_details 
 'Flack H D (1983), Acta Cryst. A39, 876-881' 
_refine_ls_abs_structure_Flack    0.003(17) 
_refine_ls_number_reflns          2646 
_refine_ls_number_parameters      218 
_refine_ls_number_restraints      2 
_refine_ls_R_factor_all           0.0369 
_refine_ls_R_factor_gt            0.0363 
_refine_ls_wR_factor_ref          0.1060 
_refine_ls_wR_factor_gt           0.1052 
_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_symmetry_multiplicity 
 _atom_site_calc_flag 
 _atom_site_refinement_flags 
 _atom_site_disorder_assembly 
 _atom_site_disorder_group 
S7 S 0.52945(3) 0.98431(9) 0.71317(6) 0.05675(17) Uani 1 1 d . . . 
O22 O 0.67432(7) 0.7174(4) 0.30178(19) 0.0708(5) Uani 1 1 d . . . 
N12 N 0.42455(7) 0.6064(4) 0.7437(2) 0.0567(5) Uani 1 1 d . . . 
C1 C 0.56595(8) 0.7428(4) 0.5223(2) 0.0470(5) Uani 1 1 d . . . 
C8 C 0.47950(8) 0.8811(4) 0.7656(2) 0.0538(5) Uani 1 1 d . . . 
C11 C 0.52849(8) 0.7577(4) 0.6023(2) 0.0471(4) Uani 1 1 d . . . 
C3 C 0.63625(9) 0.8974(5) 0.4555(3) 0.0629(6) Uani 1 1 d . . . 
H3 H 0.6594 1.0111 0.4626 0.076 Uiso 1 1 calc R . . 
C19 C 0.35413(9) 0.7051(5) 0.5269(2) 0.0580(6) Uani 1 1 d . . . 
H19 H 0.3782 0.8111 0.5495 0.070 Uiso 1 1 calc R . . 
C14 C 0.35458(9) 0.4943(4) 0.5902(2) 0.0498(5) Uani 1 1 d . . . 
C2 C 0.60106(9) 0.9123(4) 0.5288(3) 0.0600(6) Uani 1 1 d . . . 
H2 H 0.6004 1.0376 0.5841 0.072 Uiso 1 1 calc R . . 
C10 C 0.49156(8) 0.6103(4) 0.6046(2) 0.0487(5) Uani 1 1 d . . . 
H10 H 0.4853 0.4804 0.5523 0.058 Uiso 1 1 calc R . . 
C21 C 0.44917(10) 0.9275(5) 0.8557(3) 0.0628(6) Uani 1 1 d . . . 
H21 H 0.4515 1.0485 0.9148 0.075 Uiso 1 1 calc R . . 
C20 C 0.41579(9) 0.7584(5) 0.8384(2) 0.0645(6) Uani 1 1 d . . . 
H20 H 0.3907 0.7472 0.8839 0.077 Uiso 1 1 calc R . . 
C6 C 0.56834(9) 0.5600(4) 0.4376(2) 0.0544(5) Uani 1 1 d . . . 
H6 H 0.5455 0.4447 0.4312 0.065 Uiso 1 1 calc R . . 
C4 C 0.63775(8) 0.7142(5) 0.3708(2) 0.0553(5) Uani 1 1 d . . . 
C9 C 0.46404(7) 0.6833(4) 0.6981(2) 0.0488(5) Uani 1 1 d . . . 
C18 C 0.31776(11) 0.7591(5) 0.4296(3) 0.0693(7) Uani 1 1 d . . . 
H18 H 0.3179 0.9003 0.3868 0.083 Uiso 1 1 calc R . . 
C15 C 0.31737(10) 0.3427(5) 0.5569(3) 0.0635(6) Uani 1 1 d . . . 
H15 H 0.3166 0.2024 0.6002 0.076 Uiso 1 1 calc R . . 
C17 C 0.28192(11) 0.6057(7) 0.3967(3) 0.0761(8) Uani 1 1 d . . . 
H17 H 0.2578 0.6420 0.3313 0.091 Uiso 1 1 calc R . . 
C5 C 0.60360(9) 0.5442(4) 0.3627(3) 0.0555(6) Uani 1 1 d . . . 
H5 H 0.6044 0.4194 0.3070 0.067 Uiso 1 1 calc R . . 
C23 C 0.67660(11) 0.5411(6) 0.2089(3) 0.0718(8) Uani 1 1 d . . . 
H23A H 0.6483 0.5416 0.1466 0.086 Uiso 1 1 calc R . . 
H23B H 0.6797 0.3898 0.2498 0.086 Uiso 1 1 calc R . . 
C13 C 0.39441(9) 0.4189(5) 0.6909(3) 0.0611(6) Uani 1 1 d . . . 
H13A H 0.3815 0.3432 0.7601 0.073 Uiso 1 1 calc R . . 
H13B H 0.4131 0.3050 0.6534 0.073 Uiso 1 1 calc R . . 
C16 C 0.28167(11) 0.3979(7) 0.4605(3) 0.0774(8) Uani 1 1 d . . . 
H16 H 0.2572 0.2938 0.4384 0.093 Uiso 1 1 calc R . . 
C24 C 0.71830(12) 0.5901(8) 0.1438(4) 0.0883(10) Uani 1 1 d . . . 
H24A H 0.7197 0.4783 0.0769 0.132 Uiso 1 1 calc R . . 
H24B H 0.7463 0.5800 0.2053 0.132 Uiso 1 1 calc R . . 
H24C H 0.7157 0.7435 0.1076 0.132 Uiso 1 1 calc R . . 
 
 
_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 
S7 C8 1.726(3) . ? 
S7 C11 1.749(2) . ? 
O22 C4 1.370(3) . ? 
O22 C23 1.419(4) . ? 
N12 C9 1.376(3) . ? 
N12 C20 1.379(4) . ? 
N12 C13 1.446(4) . ? 
C1 C6 1.388(3) . ? 
C1 C2 1.401(3) . ? 
C1 C11 1.472(3) . ? 
C8 C9 1.381(3) . ? 
C8 C21 1.411(4) . ? 
C11 C10 1.366(3) . ? 
C3 C2 1.368(4) . ? 
C3 C4 1.386(4) . ? 
C3 H3 0.9300 . ? 
C19 C14 1.383(3) . ? 
C19 C18 1.391(4) . ? 
C19 H19 0.9300 . ? 
C14 C15 1.389(3) . ? 
C14 C13 1.509(4) . ? 
C2 H2 0.9300 . ? 
C10 C9 1.419(3) . ? 
C10 H10 0.9300 . ? 
C21 C20 1.363(4) . ? 
C21 H21 0.9300 . ? 
C20 H20 0.9300 . ? 
C6 C5 1.383(4) . ? 
C6 H6 0.9300 . ? 
C4 C5 1.383(4) . ? 
C18 C17 1.366(5) . ? 
C18 H18 0.9300 . ? 
C15 C16 1.374(5) . ? 
C15 H15 0.9300 . ? 
C17 C16 1.373(6) . ? 
C17 H17 0.9300 . ? 
C5 H5 0.9300 . ? 
C23 C24 1.499(5) . ? 
C23 H23A 0.9700 . ? 
C23 H23B 0.9700 . ? 
C13 H13A 0.9700 . ? 
C13 H13B 0.9700 . ? 
C16 H16 0.9300 . ? 
C24 H24A 0.9600 . ? 
C24 H24B 0.9600 . ? 
C24 H24C 0.9600 . ? 
 
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 
C8 S7 C11 91.52(12) . . ? 
C4 O22 C23 118.5(2) . . ? 
C9 N12 C20 107.5(2) . . ? 
C9 N12 C13 126.1(2) . . ? 
C20 N12 C13 126.0(2) . . ? 
C6 C1 C2 117.0(2) . . ? 
C6 C1 C11 121.6(2) . . ? 
C2 C1 C11 121.4(2) . . ? 
C9 C8 C21 108.5(2) . . ? 
C9 C8 S7 109.91(18) . . ? 
C21 C8 S7 141.6(2) . . ? 
C10 C11 C1 128.1(2) . . ? 
C10 C11 S7 112.71(19) . . ? 
C1 C11 S7 119.14(16) . . ? 
C2 C3 C4 120.6(2) . . ? 
C2 C3 H3 119.7 . . ? 
C4 C3 H3 119.7 . . ? 
C14 C19 C18 120.3(2) . . ? 
C14 C19 H19 119.9 . . ? 
C18 C19 H19 119.9 . . ? 
C19 C14 C15 118.5(2) . . ? 
C19 C14 C13 122.9(2) . . ? 
C15 C14 C13 118.6(2) . . ? 
C3 C2 C1 121.5(2) . . ? 
C3 C2 H2 119.3 . . ? 
C1 C2 H2 119.3 . . ? 
C11 C10 C9 110.4(2) . . ? 
C11 C10 H10 124.8 . . ? 
C9 C10 H10 124.8 . . ? 
C20 C21 C8 105.8(2) . . ? 
C20 C21 H21 127.1 . . ? 
C8 C21 H21 127.1 . . ? 
C21 C20 N12 110.3(2) . . ? 
C21 C20 H20 124.8 . . ? 
N12 C20 H20 124.8 . . ? 
C5 C6 C1 121.9(2) . . ? 
C5 C6 H6 119.0 . . ? 
C1 C6 H6 119.0 . . ? 
O22 C4 C5 125.2(2) . . ? 
O22 C4 C3 115.7(2) . . ? 
C5 C4 C3 119.2(2) . . ? 
N12 C9 C8 107.8(2) . . ? 
N12 C9 C10 136.7(2) . . ? 
C8 C9 C10 115.5(2) . . ? 
C17 C18 C19 120.3(3) . . ? 
C17 C18 H18 119.8 . . ? 
C19 C18 H18 119.8 . . ? 
C16 C15 C14 120.7(3) . . ? 
C16 C15 H15 119.6 . . ? 
C14 C15 H15 119.6 . . ? 
C18 C17 C16 119.8(3) . . ? 
C18 C17 H17 120.1 . . ? 
C16 C17 H17 120.1 . . ? 
C6 C5 C4 119.9(2) . . ? 
C6 C5 H5 120.1 . . ? 
C4 C5 H5 120.1 . . ? 
O22 C23 C24 107.7(3) . . ? 
O22 C23 H23A 110.2 . . ? 
C24 C23 H23A 110.2 . . ? 
O22 C23 H23B 110.2 . . ? 
C24 C23 H23B 110.2 . . ? 
H23A C23 H23B 108.5 . . ? 
N12 C13 C14 114.2(2) . . ? 
N12 C13 H13A 108.7 . . ? 
C14 C13 H13A 108.7 . . ? 
N12 C13 H13B 108.7 . . ? 
C14 C13 H13B 108.7 . . ? 
H13A C13 H13B 107.6 . . ? 
C17 C16 C15 120.4(3) . . ? 
C17 C16 H16 119.8 . . ? 
C15 C16 H16 119.8 . . ? 
C23 C24 H24A 109.5 . . ? 
C23 C24 H24B 109.5 . . ? 
H24A C24 H24B 109.5 . . ? 
C23 C24 H24C 109.5 . . ? 
H24A C24 H24C 109.5 . . ? 
H24B C24 H24C 109.5 . . ? 
 
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 
C11 S7 C8 C9 -0.33(18) . . . . ? 
C11 S7 C8 C21 178.3(3) . . . . ? 
C6 C1 C11 C10 -2.1(3) . . . . ? 
C2 C1 C11 C10 178.3(2) . . . . ? 
C6 C1 C11 S7 176.52(18) . . . . ? 
C2 C1 C11 S7 -3.0(3) . . . . ? 
C8 S7 C11 C10 0.32(18) . . . . ? 
C8 S7 C11 C1 -178.53(17) . . . . ? 
C18 C19 C14 C15 -1.9(4) . . . . ? 
C18 C19 C14 C13 176.1(3) . . . . ? 
C4 C3 C2 C1 0.9(4) . . . . ? 
C6 C1 C2 C3 -0.3(4) . . . . ? 
C11 C1 C2 C3 179.2(2) . . . . ? 
C1 C11 C10 C9 178.51(19) . . . . ? 
S7 C11 C10 C9 -0.2(2) . . . . ? 
C9 C8 C21 C20 -1.0(3) . . . . ? 
S7 C8 C21 C20 -179.7(2) . . . . ? 
C8 C21 C20 N12 1.3(3) . . . . ? 
C9 N12 C20 C21 -1.1(3) . . . . ? 
C13 N12 C20 C21 -173.8(2) . . . . ? 
C2 C1 C6 C5 0.0(4) . . . . ? 
C11 C1 C6 C5 -179.6(2) . . . . ? 
C23 O22 C4 C5 3.8(4) . . . . ? 
C23 O22 C4 C3 -176.9(3) . . . . ? 
C2 C3 C4 O22 179.6(3) . . . . ? 
C2 C3 C4 C5 -1.0(4) . . . . ? 
C20 N12 C9 C8 0.4(2) . . . . ? 
C13 N12 C9 C8 173.1(2) . . . . ? 
C20 N12 C9 C10 179.4(2) . . . . ? 
C13 N12 C9 C10 -8.0(4) . . . . ? 
C21 C8 C9 N12 0.4(3) . . . . ? 
S7 C8 C9 N12 179.48(15) . . . . ? 
C21 C8 C9 C10 -178.8(2) . . . . ? 
S7 C8 C9 C10 0.3(3) . . . . ? 
C11 C10 C9 N12 -178.9(2) . . . . ? 
C11 C10 C9 C8 0.0(3) . . . . ? 
C14 C19 C18 C17 0.8(4) . . . . ? 
C19 C14 C15 C16 2.0(4) . . . . ? 
C13 C14 C15 C16 -176.1(3) . . . . ? 
C19 C18 C17 C16 0.4(5) . . . . ? 
C1 C6 C5 C4 -0.2(4) . . . . ? 
O22 C4 C5 C6 179.9(2) . . . . ? 
C3 C4 C5 C6 0.7(4) . . . . ? 
C4 O22 C23 C24 177.6(3) . . . . ? 
C9 N12 C13 C14 -90.5(3) . . . . ? 
C20 N12 C13 C14 80.9(3) . . . . ? 
C19 C14 C13 N12 18.0(4) . . . . ? 
C15 C14 C13 N12 -164.0(2) . . . . ? 
C18 C17 C16 C15 -0.3(5) . . . . ? 
C14 C15 C16 C17 -0.9(5) . . . . ? 
 
_diffrn_measured_fraction_theta_max    0.984 
_diffrn_reflns_theta_full              71.18 
_diffrn_measured_fraction_theta_full   0.984 
_refine_diff_density_max    0.108 
_refine_diff_density_min   -0.191 
_refine_diff_density_rms    0.034 
