 
data_shs-20180927 
 
_audit_creation_method            SHELXL-97 
_chemical_name_systematic 
; 
 ? 
; 
_chemical_name_common             ? 
_chemical_melting_point           ? 
_chemical_formula_moiety          ? 
_chemical_formula_sum 
 'C20 H17 N S' 
_chemical_formula_weight          303.41 
 
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' 
 'N'  'N'   0.0061   0.0033 
 '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' 
 
_symmetry_cell_setting            monoclinic 
_symmetry_space_group_name_H-M    P21/c 
 
loop_ 
 _symmetry_equiv_pos_as_xyz 
 'x, y, z' 
 '-x, y+1/2, -z+1/2' 
 '-x, -y, -z' 
 'x, -y-1/2, z-1/2' 
 
_cell_length_a                    13.4137(6) 
_cell_length_b                    5.9329(2) 
_cell_length_c                    20.1416(8) 
_cell_angle_alpha                 90.00 
_cell_angle_beta                  90.210(4) 
_cell_angle_gamma                 90.00 
_cell_volume                      1602.90(11) 
_cell_formula_units_Z             4 
_cell_measurement_temperature     293(2) 
_cell_measurement_reflns_used   3096
_cell_measurement_theta_min     3.9690
_cell_measurement_theta_max     29.210
 
_exptl_crystal_description        block 
_exptl_crystal_colour             colorless 
_exptl_crystal_size_max           0.45 
_exptl_crystal_size_mid           0.28 
_exptl_crystal_size_min           0.11 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_diffrn     1.257 
_exptl_crystal_density_method     'not measured' 
_exptl_crystal_F_000              640 
_exptl_absorpt_coefficient_mu     0.198 
_exptl_absorpt_correction_type    multi-scan 
_exptl_absorpt_correction_T_min   0.9163 
_exptl_absorpt_correction_T_max   0.9786 
_exptl_absorpt_process_details    sadabs 
 
_exptl_special_details 
; 
 ? 
; 
 
_diffrn_ambient_temperature       293(2) 
_diffrn_radiation_wavelength      0.71073 
_diffrn_radiation_type            MoK\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             8879 
_diffrn_reflns_av_R_equivalents   0.0224 
_diffrn_reflns_av_sigmaI/netI     0.0353 
_diffrn_reflns_limit_h_min        -17 
_diffrn_reflns_limit_h_max        16 
_diffrn_reflns_limit_k_min        -8 
_diffrn_reflns_limit_k_max        6 
_diffrn_reflns_limit_l_min        -26 
_diffrn_reflns_limit_l_max        25 
_diffrn_reflns_theta_min          3.58 
_diffrn_reflns_theta_max          29.21 
_reflns_number_total              3702 
_reflns_number_gt                 2901 
_reflns_threshold_expression      I>2sigma(I) 
 
_computing_data_collection        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)' 
_computing_cell_refinement        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)' 
_computing_data_reduction         'CrysAlisPro 1.171.39.46 (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)+(0.0402P)²+0.6297P] 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_number_reflns          3702 
_refine_ls_number_parameters      200 
_refine_ls_number_restraints      0 
_refine_ls_R_factor_all           0.0604 
_refine_ls_R_factor_gt            0.0439 
_refine_ls_wR_factor_ref          0.1081 
_refine_ls_wR_factor_gt           0.0992 
_refine_ls_goodness_of_fit_ref    1.038 
_refine_ls_restrained_S_all       1.038 
_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_symmetry_multiplicity 
 _atom_site_calc_flag 
 _atom_site_refinement_flags 
 _atom_site_disorder_assembly 
 _atom_site_disorder_group 
S2 S 0.79805(3) 0.79393(7) 0.22362(2) 0.03264(13) Uani 1 1 d . . . 
N6 N 0.92582(11) 0.4288(3) 0.35243(7) 0.0332(3) Uani 1 1 d . . . 
C9 C 0.62853(12) 0.5344(3) 0.20031(8) 0.0283(4) Uani 1 1 d . . . 
C7 C 0.85316(13) 0.5002(3) 0.30900(8) 0.0288(4) Uani 1 1 d . . . 
C3 C 0.88478(13) 0.6997(3) 0.28063(8) 0.0304(4) Uani 1 1 d . . . 
C8 C 0.76035(13) 0.4194(3) 0.28547(8) 0.0292(4) Uani 1 1 d . . . 
H8 H 0.7301 0.2874 0.3000 0.035 Uiso 1 1 calc R . . 
C17 C 0.86582(13) 0.2588(3) 0.45781(9) 0.0307(4) Uani 1 1 d . . . 
C1 C 0.72076(12) 0.5602(3) 0.23860(8) 0.0277(4) Uani 1 1 d . . . 
C14 C 0.57040(14) 0.3405(3) 0.20591(9) 0.0340(4) Uani 1 1 d . . . 
H14 H 0.5893 0.2280 0.2356 0.041 Uiso 1 1 calc R . . 
C4 C 0.97999(14) 0.7530(3) 0.30688(9) 0.0353(4) Uani 1 1 d . . . 
H4 H 1.0195 0.8766 0.2963 0.042 Uiso 1 1 calc R . . 
C18 C 0.81349(15) 0.4518(3) 0.47293(9) 0.0371(4) Uani 1 1 d . . . 
H18 H 0.8155 0.5744 0.4442 0.045 Uiso 1 1 calc R . . 
C5 C 1.00160(13) 0.5850(3) 0.35081(9) 0.0370(4) Uani 1 1 d . . . 
H5 H 1.0596 0.5770 0.3762 0.044 Uiso 1 1 calc R . . 
C22 C 0.86313(14) 0.0793(3) 0.50238(9) 0.0365(4) Uani 1 1 d . . . 
H22 H 0.8990 -0.0512 0.4933 0.044 Uiso 1 1 calc R . . 
C20 C 0.75461(16) 0.2855(3) 0.57398(10) 0.0437(5) Uani 1 1 d . . . 
H20 H 0.7168 0.2942 0.6125 0.052 Uiso 1 1 calc R . . 
C10 C 0.59614(14) 0.6995(3) 0.15625(9) 0.0366(4) Uani 1 1 d . . . 
H10 H 0.6327 0.8319 0.1521 0.044 Uiso 1 1 calc R . . 
C21 C 0.80790(15) 0.0934(3) 0.55972(10) 0.0420(5) Uani 1 1 d . . . 
H21 H 0.8066 -0.0277 0.5890 0.050 Uiso 1 1 calc R . . 
C13 C 0.48534(14) 0.3132(3) 0.16807(9) 0.0389(4) Uani 1 1 d . . . 
H13 H 0.4480 0.1820 0.1726 0.047 Uiso 1 1 calc R . . 
C16 C 0.92243(15) 0.2300(3) 0.39385(9) 0.0385(4) Uani 1 1 d . . . 
H16A H 0.9902 0.1851 0.4044 0.046 Uiso 1 1 calc R . . 
H16B H 0.8921 0.1085 0.3687 0.046 Uiso 1 1 calc R . . 
C12 C 0.45417(14) 0.4772(3) 0.12333(9) 0.0405(5) Uani 1 1 d . . . 
C19 C 0.75784(16) 0.4645(3) 0.53063(10) 0.0448(5) Uani 1 1 d . . . 
H19 H 0.7224 0.5952 0.5401 0.054 Uiso 1 1 calc R . . 
C11 C 0.51066(15) 0.6711(3) 0.11850(10) 0.0433(5) Uani 1 1 d . . . 
H11 H 0.4909 0.7844 0.0894 0.052 Uiso 1 1 calc R . . 
C15 C 0.36166(18) 0.4433(4) 0.08217(13) 0.0649(7) Uani 1 1 d . . . 
H15A H 0.3757 0.3407 0.0466 0.097 Uiso 1 1 calc R . . 
H15B H 0.3405 0.5854 0.0642 0.097 Uiso 1 1 calc R . . 
H15C H 0.3098 0.3823 0.1095 0.097 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 
S2 C3 1.7247(18) . ? 
S2 C1 1.7583(17) . ? 
N6 C7 1.374(2) . ? 
N6 C5 1.376(2) . ? 
N6 C16 1.445(2) . ? 
C9 C10 1.390(2) . ? 
C9 C14 1.395(2) . ? 
C9 C1 1.463(2) . ? 
C7 C3 1.382(2) . ? 
C7 C8 1.414(2) . ? 
C3 C4 1.416(2) . ? 
C8 C1 1.366(2) . ? 
C8 H8 0.9300 . ? 
C17 C18 1.378(2) . ? 
C17 C22 1.393(2) . ? 
C17 C16 1.507(3) . ? 
C14 C13 1.379(3) . ? 
C14 H14 0.9300 . ? 
C4 C5 1.363(3) . ? 
C4 H4 0.9300 . ? 
C18 C19 1.386(3) . ? 
C18 H18 0.9300 . ? 
C5 H5 0.9300 . ? 
C22 C21 1.377(3) . ? 
C22 H22 0.9300 . ? 
C20 C19 1.376(3) . ? 
C20 C21 1.376(3) . ? 
C20 H20 0.9300 . ? 
C10 C11 1.384(3) . ? 
C10 H10 0.9300 . ? 
C21 H21 0.9300 . ? 
C13 C12 1.390(3) . ? 
C13 H13 0.9300 . ? 
C16 H16A 0.9700 . ? 
C16 H16B 0.9700 . ? 
C12 C11 1.381(3) . ? 
C12 C15 1.503(3) . ? 
C19 H19 0.9300 . ? 
C11 H11 0.9300 . ? 
C15 H15A 0.9600 . ? 
C15 H15B 0.9600 . ? 
C15 H15C 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 
C3 S2 C1 91.53(8) . . ? 
C7 N6 C5 107.44(15) . . ? 
C7 N6 C16 126.53(15) . . ? 
C5 N6 C16 126.01(15) . . ? 
C10 C9 C14 117.33(16) . . ? 
C10 C9 C1 121.65(16) . . ? 
C14 C9 C1 121.02(15) . . ? 
N6 C7 C3 108.02(15) . . ? 
N6 C7 C8 136.91(16) . . ? 
C3 C7 C8 115.01(15) . . ? 
C7 C3 C4 108.33(16) . . ? 
C7 C3 S2 110.23(13) . . ? 
C4 C3 S2 141.38(14) . . ? 
C1 C8 C7 111.34(15) . . ? 
C1 C8 H8 124.3 . . ? 
C7 C8 H8 124.3 . . ? 
C18 C17 C22 118.57(17) . . ? 
C18 C17 C16 122.80(16) . . ? 
C22 C17 C16 118.59(16) . . ? 
C8 C1 C9 128.76(15) . . ? 
C8 C1 S2 111.88(13) . . ? 
C9 C1 S2 119.32(12) . . ? 
C13 C14 C9 120.93(17) . . ? 
C13 C14 H14 119.5 . . ? 
C9 C14 H14 119.5 . . ? 
C5 C4 C3 105.57(16) . . ? 
C5 C4 H4 127.2 . . ? 
C3 C4 H4 127.2 . . ? 
C17 C18 C19 120.46(17) . . ? 
C17 C18 H18 119.8 . . ? 
C19 C18 H18 119.8 . . ? 
C4 C5 N6 110.63(16) . . ? 
C4 C5 H5 124.7 . . ? 
N6 C5 H5 124.7 . . ? 
C21 C22 C17 120.63(17) . . ? 
C21 C22 H22 119.7 . . ? 
C17 C22 H22 119.7 . . ? 
C19 C20 C21 119.29(19) . . ? 
C19 C20 H20 120.4 . . ? 
C21 C20 H20 120.4 . . ? 
C11 C10 C9 121.43(17) . . ? 
C11 C10 H10 119.3 . . ? 
C9 C10 H10 119.3 . . ? 
C20 C21 C22 120.45(18) . . ? 
C20 C21 H21 119.8 . . ? 
C22 C21 H21 119.8 . . ? 
C14 C13 C12 121.48(17) . . ? 
C14 C13 H13 119.3 . . ? 
C12 C13 H13 119.3 . . ? 
N6 C16 C17 114.70(14) . . ? 
N6 C16 H16A 108.6 . . ? 
C17 C16 H16A 108.6 . . ? 
N6 C16 H16B 108.6 . . ? 
C17 C16 H16B 108.6 . . ? 
H16A C16 H16B 107.6 . . ? 
C11 C12 C13 117.72(17) . . ? 
C11 C12 C15 121.62(19) . . ? 
C13 C12 C15 120.65(19) . . ? 
C20 C19 C18 120.59(18) . . ? 
C20 C19 H19 119.7 . . ? 
C18 C19 H19 119.7 . . ? 
C12 C11 C10 121.09(18) . . ? 
C12 C11 H11 119.5 . . ? 
C10 C11 H11 119.5 . . ? 
C12 C15 H15A 109.5 . . ? 
C12 C15 H15B 109.5 . . ? 
H15A C15 H15B 109.5 . . ? 
C12 C15 H15C 109.5 . . ? 
H15A C15 H15C 109.5 . . ? 
H15B C15 H15C 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 
C5 N6 C7 C3 0.24(19) . . . . ? 
C16 N6 C7 C3 178.52(15) . . . . ? 
C5 N6 C7 C8 177.31(19) . . . . ? 
C16 N6 C7 C8 -4.4(3) . . . . ? 
N6 C7 C3 C4 0.36(19) . . . . ? 
C8 C7 C3 C4 -177.43(15) . . . . ? 
N6 C7 C3 S2 178.25(11) . . . . ? 
C8 C7 C3 S2 0.46(19) . . . . ? 
C1 S2 C3 C7 -0.47(13) . . . . ? 
C1 S2 C3 C4 176.3(2) . . . . ? 
N6 C7 C8 C1 -177.09(19) . . . . ? 
C3 C7 C8 C1 -0.2(2) . . . . ? 
C7 C8 C1 C9 177.49(16) . . . . ? 
C7 C8 C1 S2 -0.20(18) . . . . ? 
C10 C9 C1 C8 177.02(17) . . . . ? 
C14 C9 C1 C8 -4.1(3) . . . . ? 
C10 C9 C1 S2 -5.4(2) . . . . ? 
C14 C9 C1 S2 173.48(13) . . . . ? 
C3 S2 C1 C8 0.39(13) . . . . ? 
C3 S2 C1 C9 -177.55(13) . . . . ? 
C10 C9 C14 C13 1.2(3) . . . . ? 
C1 C9 C14 C13 -177.73(16) . . . . ? 
C7 C3 C4 C5 -0.81(19) . . . . ? 
S2 C3 C4 C5 -177.64(17) . . . . ? 
C22 C17 C18 C19 -1.3(3) . . . . ? 
C16 C17 C18 C19 176.14(18) . . . . ? 
C3 C4 C5 N6 1.0(2) . . . . ? 
C7 N6 C5 C4 -0.8(2) . . . . ? 
C16 N6 C5 C4 -179.08(16) . . . . ? 
C18 C17 C22 C21 1.1(3) . . . . ? 
C16 C17 C22 C21 -176.44(17) . . . . ? 
C14 C9 C10 C11 -1.2(3) . . . . ? 
C1 C9 C10 C11 177.79(17) . . . . ? 
C19 C20 C21 C22 -0.6(3) . . . . ? 
C17 C22 C21 C20 -0.1(3) . . . . ? 
C9 C14 C13 C12 -0.2(3) . . . . ? 
C7 N6 C16 C17 -82.3(2) . . . . ? 
C5 N6 C16 C17 95.7(2) . . . . ? 
C18 C17 C16 N6 5.8(3) . . . . ? 
C22 C17 C16 N6 -176.71(15) . . . . ? 
C14 C13 C12 C11 -0.8(3) . . . . ? 
C14 C13 C12 C15 179.5(2) . . . . ? 
C21 C20 C19 C18 0.5(3) . . . . ? 
C17 C18 C19 C20 0.5(3) . . . . ? 
C13 C12 C11 C10 0.9(3) . . . . ? 
C15 C12 C11 C10 -179.5(2) . . . . ? 
C9 C10 C11 C12 0.1(3) . . . . ? 
 
_diffrn_measured_fraction_theta_max    0.977 
_diffrn_reflns_theta_full              29.21 
_diffrn_measured_fraction_theta_full   0.977 
_refine_diff_density_max    0.218 
_refine_diff_density_min   -0.236 
_refine_diff_density_rms    0.044 
