 
data_ic17628 
  
_audit_creation_method            'SHELXL-2014/7' 
_shelx_SHELXL_version_number      '2014/7' 
_chemical_name_systematic         ? 
_chemical_name_common             ? 
_chemical_melting_point           ? 
_chemical_formula_moiety          ? 
_chemical_formula_sum 
 'C20 H18 N2 O2 S2' 
_chemical_formula_weight          382.48 
  
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' 
  
_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                    4.48290(10) 
_cell_length_b                    18.7740(5) 
_cell_length_c                    10.3924(3) 
_cell_angle_alpha                 90 
_cell_angle_beta                  92.2717(11) 
_cell_angle_gamma                 90 
_cell_volume                      873.96(4) 
_cell_formula_units_Z             2 
_cell_measurement_temperature     200(2) 
_cell_measurement_reflns_used     6325 
_cell_measurement_theta_min       4.26 
_cell_measurement_theta_max       70.48 
  
_exptl_crystal_description        needle 
_exptl_crystal_colour             yellow 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_method     ? 
_exptl_crystal_density_diffrn     1.453 
_exptl_crystal_F_000              400 
_exptl_transmission_factor_min    ? 
_exptl_transmission_factor_max    ? 
_exptl_crystal_size_max           0.400 
_exptl_crystal_size_mid           0.070 
_exptl_crystal_size_min           0.060 
_exptl_absorpt_coefficient_mu     2.907 
_shelx_estimated_absorpt_T_min    0.389 
_shelx_estimated_absorpt_T_max    0.845 
_exptl_absorpt_correction_type    multi-scan 
_exptl_absorpt_correction_T_min   0.5260 
_exptl_absorpt_correction_T_max   0.7533 
_exptl_absorpt_process_details    'SADABS (Bruker, 2014)'
_exptl_absorpt_special_details    ? 
_diffrn_ambient_temperature       200(2) 
_diffrn_radiation_wavelength      1.54178 
_diffrn_radiation_type            CuK\a 
_diffrn_source                    ? 
_diffrn_measurement_device_type   'Bruker D8 VENTURE' 
_diffrn_measurement_method        'φ and ω scans' 
_diffrn_detector_area_resol_mean  ? 
_diffrn_reflns_number             5422 
_diffrn_reflns_av_unetI/netI      0.0278 
_diffrn_reflns_av_R_equivalents   0.0291 
_diffrn_reflns_limit_h_min        -5 
_diffrn_reflns_limit_h_max        5 
_diffrn_reflns_limit_k_min        -22 
_diffrn_reflns_limit_k_max        22 
_diffrn_reflns_limit_l_min        -12 
_diffrn_reflns_limit_l_max        12 
_diffrn_reflns_theta_min          4.711 
_diffrn_reflns_theta_max          69.976 
_diffrn_reflns_theta_full         67.679 
_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              1665 
_reflns_number_gt                 1532 
_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 APEX3' 
_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)+(0.0578P)²+0.2915P] 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          1665 
_refine_ls_number_parameters      120 
_refine_ls_number_restraints      0 
_refine_ls_R_factor_all           0.0354 
_refine_ls_R_factor_gt            0.0327 
_refine_ls_wR_factor_ref          0.0931 
_refine_ls_wR_factor_gt           0.0907 
_refine_ls_goodness_of_fit_ref    1.048 
_refine_ls_restrained_S_all       1.048 
_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 0.22897(8) 0.50463(2) 0.65442(3) 0.02298(16) Uani 1 1 d . . . . . 
O1 O -0.0708(3) 0.43016(6) 0.82399(12) 0.0338(3) Uani 1 1 d . . . . . 
N1 N 0.4787(3) 0.40549(7) 0.51886(12) 0.0227(3) Uani 1 1 d . . . . . 
C1 C 0.5532(3) 0.47002(8) 0.47124(14) 0.0206(3) Uani 1 1 d . . . . . 
C2 C 0.3072(3) 0.41495(8) 0.61705(14) 0.0207(3) Uani 1 1 d . . . . . 
C3 C 0.1976(3) 0.35427(8) 0.69165(14) 0.0214(3) Uani 1 1 d . . . . . 
C4 C 0.2902(4) 0.28574(8) 0.65956(14) 0.0241(3) Uani 1 1 d . . . . . 
H4 H 0.4157 0.2799 0.5888 0.029 Uiso 1 1 calc R U . . . 
C5 C 0.2053(4) 0.22577(9) 0.72750(15) 0.0263(4) Uani 1 1 d . . . . . 
C6 C 0.0208(4) 0.23545(9) 0.83076(15) 0.0294(4) Uani 1 1 d . . . . . 
H6 H -0.0391 0.1952 0.8787 0.035 Uiso 1 1 calc R U . . . 
C7 C -0.0771(4) 0.30244(9) 0.86507(15) 0.0296(4) Uani 1 1 d . . . . . 
H7 H -0.2038 0.3079 0.9355 0.035 Uiso 1 1 calc R U . . . 
C8 C 0.0107(4) 0.36190(8) 0.79599(15) 0.0251(3) Uani 1 1 d . . . . . 
C9 C 0.3166(4) 0.15334(9) 0.69130(18) 0.0351(4) Uani 1 1 d . . . . . 
H9A H 0.2905 0.1468 0.5980 0.053 Uiso 1 1 calc R U . . . 
H9B H 0.2032 0.1168 0.7356 0.053 Uiso 1 1 calc R U . . . 
H9C H 0.5287 0.1492 0.7167 0.053 Uiso 1 1 calc R U . . . 
C10 C -0.2714(4) 0.44193(10) 0.92407(16) 0.0313(4) Uani 1 1 d . . . . . 
H10A H -0.4555 0.4149 0.9061 0.047 Uiso 1 1 calc R U . . . 
H10B H -0.3182 0.4928 0.9290 0.047 Uiso 1 1 calc R U . . . 
H10C H -0.1790 0.4261 1.0062 0.047 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 C1 1.7280(15) 3_666 ? 
S1 C2 1.7661(15) . ? 
O1 C8 1.367(2) . ? 
O1 C10 1.4190(19) . ? 
N1 C2 1.314(2) . ? 
N1 C1 1.355(2) . ? 
C1 C1 1.369(3) 3_666 ? 
C1 S1 1.7280(15) 3_666 ? 
C2 C3 1.473(2) . ? 
C3 C4 1.396(2) . ? 
C3 C8 1.403(2) . ? 
C4 C5 1.390(2) . ? 
C4 H4 0.9500 . ? 
C5 C6 1.392(2) . ? 
C5 C9 1.501(2) . ? 
C6 C7 1.383(2) . ? 
C6 H6 0.9500 . ? 
C7 C8 1.393(2) . ? 
C7 H7 0.9500 . ? 
C9 H9A 0.9800 . ? 
C9 H9B 0.9800 . ? 
C9 H9C 0.9800 . ? 
C10 H10A 0.9800 . ? 
C10 H10B 0.9800 . ? 
C10 H10C 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 
C1 S1 C2 88.48(7) 3_666 . ? 
C8 O1 C10 118.97(13) . . ? 
C2 N1 C1 108.85(13) . . ? 
N1 C1 C1 118.69(17) . 3_666 ? 
N1 C1 S1 132.60(12) . 3_666 ? 
C1 C1 S1 108.70(15) 3_666 3_666 ? 
N1 C2 C3 121.46(13) . . ? 
N1 C2 S1 115.28(11) . . ? 
C3 C2 S1 123.24(11) . . ? 
C4 C3 C8 118.08(14) . . ? 
C4 C3 C2 118.57(14) . . ? 
C8 C3 C2 123.32(14) . . ? 
C5 C4 C3 122.35(15) . . ? 
C5 C4 H4 118.8 . . ? 
C3 C4 H4 118.8 . . ? 
C4 C5 C6 117.94(15) . . ? 
C4 C5 C9 120.39(15) . . ? 
C6 C5 C9 121.66(15) . . ? 
C7 C6 C5 121.43(15) . . ? 
C7 C6 H6 119.3 . . ? 
C5 C6 H6 119.3 . . ? 
C6 C7 C8 119.79(15) . . ? 
C6 C7 H7 120.1 . . ? 
C8 C7 H7 120.1 . . ? 
O1 C8 C7 123.94(14) . . ? 
O1 C8 C3 115.65(14) . . ? 
C7 C8 C3 120.40(15) . . ? 
C5 C9 H9A 109.5 . . ? 
C5 C9 H9B 109.5 . . ? 
H9A C9 H9B 109.5 . . ? 
C5 C9 H9C 109.5 . . ? 
H9A C9 H9C 109.5 . . ? 
H9B C9 H9C 109.5 . . ? 
O1 C10 H10A 109.5 . . ? 
O1 C10 H10B 109.5 . . ? 
H10A C10 H10B 109.5 . . ? 
O1 C10 H10C 109.5 . . ? 
H10A C10 H10C 109.5 . . ? 
H10B C10 H10C 109.5 . . ? 
  
_refine_diff_density_max    0.318 
_refine_diff_density_min   -0.309 
_refine_diff_density_rms    0.062 
  
  
  
