# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_I
_database_code_depnum_ccdc_archive 'CCDC 1859352'
_audit_update_record             
;
2018-07-31 deposited with the CCDC.
2018-10-03 downloaded from the CCDC.
;
_chemical_name_systematic        
N-Phenyl-N'-propyl-6-phenyl-2-iminotetrahydro-1,3-thiazin-4-one
_chemical_name_common            2h
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H20 N2 O S'
_chemical_formula_iupac          ?
_chemical_formula_weight         324.43

_chemical_melting_point          164-165

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   12.8458(5)
_cell_length_b                   5.3427(2)
_cell_length_c                   24.6144(10)
_cell_angle_alpha                90
_cell_angle_beta                 101.767(3)
_cell_angle_gamma                90
_cell_volume                     1653.82(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2343
_cell_measurement_theta_min      3.5145
_cell_measurement_theta_max      68.1837
_cell_measurement_temperature    173

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.050
_exptl_crystal_density_diffrn    1.303
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             688

_exptl_absorpt_coefficient_mu    1.776
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/5 (Bruker AXS Inc.)'
_exptl_absorpt_correction_T_min  0.76
_exptl_absorpt_correction_T_max  0.92

_exptl_special_details           
;
;

_diffrn_ambient_temperature      173

_diffrn_source                   ?
_diffrn_source_type              ?

_diffrn_radiation_type           ?
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  ?

_diffrn_measurement_device_type  'BRUKER APEXII CCD'
_diffrn_measurement_method       ?

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            10898
_diffrn_reflns_av_R_equivalents  0.0375
_diffrn_reflns_av_unetI/netI     0.0341
_diffrn_reflns_theta_min         3.51
_diffrn_reflns_theta_max         68.34
_diffrn_reflns_theta_full        68.34
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measured_fraction_theta_full 0.987
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       28

_refine_special_details          
;
;

_reflns_number_total             3012
_reflns_number_gt                2264
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0696
_refine_ls_R_factor_gt           0.0495
_refine_ls_wR_factor_gt          0.1324
_refine_ls_wR_factor_ref         0.1416
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_restrained_S_all      1.007
_refine_ls_number_reflns         3012
_refine_ls_number_parameters     209
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0952P)²+0.1574P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.588
_refine_diff_density_min         -0.300
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'

_computing_data_collection       ?
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.30702(17) 0.3667(4) 0.62829(9) 0.0265(5) Uani d . . . 1 . .
C C2 0.28377(18) 0.4694(4) 0.73682(10) 0.0275(5) Uani d . . . 1 . .
H H2 0.3426 0.3518 0.7529 0.033 Uiso calc U . R 1 . .
C C3 0.3313(2) 0.7165(5) 0.72503(10) 0.0324(5) Uani d . . . 1 . .
H H3A 0.2732 0.8289 0.7069 0.039 Uiso calc U . R 1 . .
H H3B 0.3655 0.7942 0.7607 0.039 Uiso calc U . R 1 . .
C C4 0.41182(18) 0.6971(4) 0.68872(10) 0.0294(5) Uani d . . . 1 . .
C C5 0.20684(19) 0.0766(5) 0.56827(11) 0.0339(6) Uani d . . . 1 . .
H H5A 0.1402 0.167 0.5697 0.041 Uiso calc U . R 1 . .
H H5B 0.2149 -0.0608 0.5958 0.041 Uiso calc U . R 1 . .
C C6 0.1993(2) -0.0325(6) 0.51114(11) 0.0419(6) Uani d . . . 1 . .
H H6A 0.27 -0.0966 0.5078 0.05 Uiso calc U . R 1 . .
H H6B 0.1792 0.1016 0.4832 0.05 Uiso calc U . R 1 . .
C C7 0.1184(2) -0.2437(5) 0.49873(13) 0.0447(7) Uani d . . . 1 . .
H H7A 0.1384 -0.3782 0.5259 0.067 Uiso calc U . R 1 . .
H H7B 0.1169 -0.3087 0.4614 0.067 Uiso calc U . R 1 . .
H H7C 0.0478 -0.1801 0.5009 0.067 Uiso calc U . R 1 . .
C C8 0.47934(17) 0.5169(4) 0.61277(9) 0.0268(5) Uani d . . . 1 . .
C C9 0.55035(19) 0.3216(5) 0.61986(10) 0.0300(5) Uani d . . . 1 . .
H H9 0.5438 0.1883 0.6445 0.036 Uiso calc U . R 1 . .
C C10 0.63216(19) 0.3221(5) 0.59038(11) 0.0330(5) Uani d . . . 1 . .
H H10 0.6829 0.1903 0.5955 0.04 Uiso calc U . R 1 . .
C C11 0.63962(19) 0.5141(5) 0.55370(10) 0.0331(5) Uani d . . . 1 . .
H H11 0.6947 0.5125 0.5332 0.04 Uiso calc U . R 1 . .
C C12 0.5673(2) 0.7078(5) 0.54689(10) 0.0321(5) Uani d . . . 1 . .
H H12 0.5728 0.8393 0.5216 0.039 Uiso calc U . R 1 . .
C C13 0.48635(19) 0.7119(4) 0.57680(10) 0.0297(5) Uani d . . . 1 . .
H H13 0.4369 0.8462 0.5726 0.036 Uiso calc U . R 1 . .
C C14 0.20644(18) 0.4833(5) 0.77554(9) 0.0279(5) Uani d . . . 1 . .
C C15 0.2112(2) 0.3037(5) 0.81660(10) 0.0346(6) Uani d . . . 1 . .
H H15 0.2642 0.1771 0.8208 0.042 Uiso calc U . R 1 . .
C C16 0.1392(2) 0.3081(6) 0.85152(11) 0.0422(6) Uani d . . . 1 . .
H H16 0.1425 0.1835 0.8794 0.051 Uiso calc U . R 1 . .
C C17 0.0628(2) 0.4921(6) 0.84603(12) 0.0449(7) Uani d . . . 1 . .
H H17 0.0133 0.494 0.8699 0.054 Uiso calc U . R 1 . .
C C18 0.0581(2) 0.6733(6) 0.80591(13) 0.0445(7) Uani d . . . 1 . .
H H18 0.0061 0.8019 0.8026 0.053 Uiso calc U . R 1 . .
C C19 0.1291(2) 0.6688(5) 0.77030(11) 0.0369(6) Uani d . . . 1 . .
H H19 0.1249 0.7928 0.7423 0.044 Uiso calc U . R 1 . .
N N1 0.39654(15) 0.5240(4) 0.64566(8) 0.0278(4) Uani d . . . 1 . .
N N2 0.29671(15) 0.2486(4) 0.58298(8) 0.0306(5) Uani d . . . 1 . .
O O1 0.48952(14) 0.8331(4) 0.69661(7) 0.0399(5) Uani d . . . 1 . .
S S1 0.21156(4) 0.34229(12) 0.67082(3) 0.0323(2) Uani d . . . 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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 N2 . 1.265(3) ?
C1 N1 . 1.418(3) ?
C1 S1 . 1.772(2) ?
C2 C3 . 1.507(3) ?
C2 C14 . 1.512(3) ?
C2 S1 . 1.829(2) ?
C2 H2 . 1.0 ?
C3 C4 . 1.503(3) ?
C3 H3A . 0.99 ?
C3 H3B . 0.99 ?
C4 O1 . 1.218(3) ?
C4 N1 . 1.390(3) ?
C5 N2 . 1.462(3) ?
C5 C6 . 1.507(3) ?
C5 H5A . 0.99 ?
C5 H5B . 0.99 ?
C6 C7 . 1.522(4) ?
C6 H6A . 0.99 ?
C6 H6B . 0.99 ?
C7 H7A . 0.98 ?
C7 H7B . 0.98 ?
C7 H7C . 0.98 ?
C8 C9 . 1.373(3) ?
C8 C13 . 1.382(3) ?
C8 N1 . 1.463(3) ?
C9 C10 . 1.394(3) ?
C9 H9 . 0.95 ?
C10 C11 . 1.383(4) ?
C10 H10 . 0.95 ?
C11 C12 . 1.378(4) ?
C11 H11 . 0.95 ?
C12 C13 . 1.392(3) ?
C12 H12 . 0.95 ?
C13 H13 . 0.95 ?
C14 C15 . 1.386(3) ?
C14 C19 . 1.391(3) ?
C15 C16 . 1.386(3) ?
C15 H15 . 0.95 ?
C16 C17 . 1.376(4) ?
C16 H16 . 0.95 ?
C17 C18 . 1.375(4) ?
C17 H17 . 0.95 ?
C18 C19 . 1.388(4) ?
C18 H18 . 0.95 ?
C19 H19 . 0.95 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N2 C1 N1 . . 119.6(2) ?
N2 C1 S1 . . 121.58(17) ?
N1 C1 S1 . . 118.80(16) ?
C3 C2 C14 . . 114.96(19) ?
C3 C2 S1 . . 107.82(16) ?
C14 C2 S1 . . 107.38(15) ?
C3 C2 H2 . . 108.8 ?
C14 C2 H2 . . 108.8 ?
S1 C2 H2 . . 108.8 ?
C4 C3 C2 . . 114.2(2) ?
C4 C3 H3A . . 108.7 ?
C2 C3 H3A . . 108.7 ?
C4 C3 H3B . . 108.7 ?
C2 C3 H3B . . 108.7 ?
H3A C3 H3B . . 107.6 ?
O1 C4 N1 . . 120.2(2) ?
O1 C4 C3 . . 120.4(2) ?
N1 C4 C3 . . 119.5(2) ?
N2 C5 C6 . . 111.8(2) ?
N2 C5 H5A . . 109.3 ?
C6 C5 H5A . . 109.3 ?
N2 C5 H5B . . 109.3 ?
C6 C5 H5B . . 109.3 ?
H5A C5 H5B . . 107.9 ?
C5 C6 C7 . . 112.7(2) ?
C5 C6 H6A . . 109.1 ?
C7 C6 H6A . . 109.1 ?
C5 C6 H6B . . 109.1 ?
C7 C6 H6B . . 109.1 ?
H6A C6 H6B . . 107.8 ?
C6 C7 H7A . . 109.5 ?
C6 C7 H7B . . 109.5 ?
H7A C7 H7B . . 109.5 ?
C6 C7 H7C . . 109.5 ?
H7A C7 H7C . . 109.5 ?
H7B C7 H7C . . 109.5 ?
C9 C8 C13 . . 121.7(2) ?
C9 C8 N1 . . 119.2(2) ?
C13 C8 N1 . . 119.0(2) ?
C8 C9 C10 . . 119.0(2) ?
C8 C9 H9 . . 120.5 ?
C10 C9 H9 . . 120.5 ?
C11 C10 C9 . . 120.1(2) ?
C11 C10 H10 . . 120.0 ?
C9 C10 H10 . . 120.0 ?
C12 C11 C10 . . 120.1(2) ?
C12 C11 H11 . . 119.9 ?
C10 C11 H11 . . 119.9 ?
C11 C12 C13 . . 120.4(2) ?
C11 C12 H12 . . 119.8 ?
C13 C12 H12 . . 119.8 ?
C8 C13 C12 . . 118.7(2) ?
C8 C13 H13 . . 120.6 ?
C12 C13 H13 . . 120.6 ?
C15 C14 C19 . . 119.1(2) ?
C15 C14 C2 . . 119.2(2) ?
C19 C14 C2 . . 121.7(2) ?
C14 C15 C16 . . 120.3(2) ?
C14 C15 H15 . . 119.8 ?
C16 C15 H15 . . 119.8 ?
C17 C16 C15 . . 120.3(3) ?
C17 C16 H16 . . 119.9 ?
C15 C16 H16 . . 119.9 ?
C18 C17 C16 . . 119.9(2) ?
C18 C17 H17 . . 120.0 ?
C16 C17 H17 . . 120.0 ?
C17 C18 C19 . . 120.2(3) ?
C17 C18 H18 . . 119.9 ?
C19 C18 H18 . . 119.9 ?
C18 C19 C14 . . 120.2(2) ?
C18 C19 H19 . . 119.9 ?
C14 C19 H19 . . 119.9 ?
C4 N1 C1 . . 127.16(19) ?
C4 N1 C8 . . 115.70(18) ?
C1 N1 C8 . . 117.01(18) ?
C1 N2 C5 . . 117.86(19) ?
C1 S1 C2 . . 102.16(11) ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C14 C2 C3 C4 . . . . 177.19(19) ?
S1 C2 C3 C4 . . . . -63.1(2) ?
C2 C3 C4 O1 . . . . -143.9(2) ?
C2 C3 C4 N1 . . . . 36.7(3) ?
N2 C5 C6 C7 . . . . 170.4(2) ?
C13 C8 C9 C10 . . . . 0.7(4) ?
N1 C8 C9 C10 . . . . -176.9(2) ?
C8 C9 C10 C11 . . . . -1.4(4) ?
C9 C10 C11 C12 . . . . 1.1(4) ?
C10 C11 C12 C13 . . . . 0.0(4) ?
C9 C8 C13 C12 . . . . 0.4(4) ?
N1 C8 C13 C12 . . . . 178.1(2) ?
C11 C12 C13 C8 . . . . -0.8(4) ?
C3 C2 C14 C15 . . . . -137.3(2) ?
S1 C2 C14 C15 . . . . 102.8(2) ?
C3 C2 C14 C19 . . . . 44.1(3) ?
S1 C2 C14 C19 . . . . -75.9(3) ?
C19 C14 C15 C16 . . . . 0.6(4) ?
C2 C14 C15 C16 . . . . -178.0(2) ?
C14 C15 C16 C17 . . . . -0.6(4) ?
C15 C16 C17 C18 . . . . -0.3(4) ?
C16 C17 C18 C19 . . . . 1.1(5) ?
C17 C18 C19 C14 . . . . -1.0(4) ?
C15 C14 C19 C18 . . . . 0.1(4) ?
C2 C14 C19 C18 . . . . 178.8(2) ?
O1 C4 N1 C1 . . . . -174.7(2) ?
C3 C4 N1 C1 . . . . 4.8(4) ?
O1 C4 N1 C8 . . . . 1.0(3) ?
C3 C4 N1 C8 . . . . -179.5(2) ?
N2 C1 N1 C4 . . . . 168.5(2) ?
S1 C1 N1 C4 . . . . -11.2(3) ?
N2 C1 N1 C8 . . . . -7.2(3) ?
S1 C1 N1 C8 . . . . 173.18(16) ?
C9 C8 N1 C4 . . . . 105.5(2) ?
C13 C8 N1 C4 . . . . -72.2(3) ?
C9 C8 N1 C1 . . . . -78.4(3) ?
C13 C8 N1 C1 . . . . 104.0(3) ?
N1 C1 N2 C5 . . . . 176.3(2) ?
S1 C1 N2 C5 . . . . -4.1(3) ?
C6 C5 N2 C1 . . . . 174.9(2) ?
N2 C1 S1 C2 . . . . 164.1(2) ?
N1 C1 S1 C2 . . . . -16.2(2) ?
C3 C2 S1 C1 . . . . 49.95(18) ?
C14 C2 S1 C1 . . . . 174.36(16) ?


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: CHCl3 and Hexane'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_I_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1859353'
_audit_update_record             
;
2018-07-31 deposited with the CCDC.
2018-10-03 downloaded from the CCDC.
;
_chemical_name_systematic        
N-Phenyl-N'-isopropyl-6-phenyl-2-iminotetrahydro-1,3-thiazin-4-one
_chemical_name_common            2i
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H20 N2 O S'
_chemical_formula_iupac          ?
_chemical_formula_weight         324.43

_chemical_melting_point          150-152

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   13.0104(7)
_cell_length_b                   5.4301(3)
_cell_length_c                   24.2997(15)
_cell_angle_alpha                90
_cell_angle_beta                 101.772(4)
_cell_angle_gamma                90
_cell_volume                     1680.61(17)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4390
_cell_measurement_theta_min      3.4701
_cell_measurement_theta_max      68.0866
_cell_measurement_temperature    173

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.050
_exptl_crystal_density_diffrn    1.282
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             688

_exptl_absorpt_coefficient_mu    1.747
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'SADABS (Sheldrick 1996)'
_exptl_absorpt_correction_T_min  0.84
_exptl_absorpt_correction_T_max  0.92

_exptl_special_details           'SADABS (Sheldrick 1996)'

_diffrn_ambient_temperature      173

_diffrn_source                   'Bruker TXS fine-focus rotating anode'
_diffrn_source_type              ?

_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  'Bruker Helios multilayer confocal mirror'

_diffrn_measurement_device_type  'Bruker APEXII Ultra CCD area detector'
_diffrn_measurement_method       'Phi and Omega scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            11611
_diffrn_reflns_av_R_equivalents  0.0269
_diffrn_reflns_av_unetI/netI     0.0243
_diffrn_reflns_theta_min         3.47
_diffrn_reflns_theta_max         68.24
_diffrn_reflns_theta_full        68.24
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       29

_refine_special_details          
;
;

_reflns_number_total             3051
_reflns_number_gt                2600
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0546
_refine_ls_R_factor_gt           0.0469
_refine_ls_wR_factor_gt          0.1317
_refine_ls_wR_factor_ref         0.1377
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_restrained_S_all      1.055
_refine_ls_number_reflns         3051
_refine_ls_number_parameters     210
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0914P)²+0.4481P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.361
_refine_diff_density_min         -0.290
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'

_computing_data_collection       'APEX2 (Bruker AXS, 2006)'
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'XSHEL (Bruker AXS,2002)'
_computing_publication_material  'XCIF (Bruker AXS, 2001)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.30589(15) 0.6509(4) 0.44152(8) 0.0338(4) Uani d . . . 1 . .
H H1 0.3265 0.5644 0.4091 0.041 Uiso calc U . R 1 . .
C C2 0.39426(17) 0.8170(4) 0.46917(11) 0.0490(6) Uani d . . . 1 . .
H H2A 0.4057 0.9446 0.4425 0.073 Uiso calc U . R 1 . .
H H2B 0.4585 0.7198 0.4807 0.073 Uiso calc U . R 1 . .
H H2C 0.376 0.8947 0.5023 0.073 Uiso calc U . R 1 . .
C C3 0.28284(17) 0.4613(4) 0.48327(10) 0.0437(5) Uani d . . . 1 . .
H H3A 0.2592 0.5451 0.5142 0.066 Uiso calc U . R 1 . .
H H3B 0.3467 0.3671 0.4982 0.066 Uiso calc U . R 1 . .
H H3C 0.2277 0.3493 0.4644 0.066 Uiso calc U . R 1 . .
C C4 0.19699(14) 0.8980(4) 0.37329(8) 0.0297(4) Uani d . . . 1 . .
C C5 0.21779(14) 0.9919(4) 0.26265(8) 0.0324(4) Uani d . . . 1 . .
H H5 0.1604 0.874 0.2467 0.039 Uiso calc U . R 1 . .
C C6 0.16971(16) 1.2340(4) 0.27406(9) 0.0374(5) Uani d . . . 1 . .
H H6A 0.1369 1.3111 0.2378 0.045 Uiso calc U . R 1 . .
H H6B 0.2259 1.3453 0.2933 0.045 Uiso calc U . R 1 . .
C C7 0.08823(15) 1.2075(4) 0.30971(8) 0.0346(4) Uani d . . . 1 . .
C C8 0.29463(14) 1.0063(4) 0.22341(8) 0.0328(4) Uani d . . . 1 . .
C C9 0.29069(17) 0.8278(4) 0.18238(9) 0.0396(5) Uani d . . . 1 . .
H H9 0.2395 0.7008 0.1786 0.048 Uiso calc U . R 1 . .
C C10 0.3618(2) 0.8348(5) 0.14675(10) 0.0506(6) Uani d . . . 1 . .
H H10 0.3592 0.7118 0.1187 0.061 Uiso calc U . R 1 . .
C C11 0.43553(19) 1.0183(5) 0.15192(11) 0.0535(6) Uani d . . . 1 . .
H H11 0.4841 1.0219 0.1275 0.064 Uiso calc U . R 1 . .
C C12 0.43933(18) 1.1970(5) 0.19234(11) 0.0529(6) Uani d . . . 1 . .
H H12 0.4899 1.3252 0.1955 0.064 Uiso calc U . R 1 . .
C C13 0.36960(17) 1.1909(4) 0.22850(10) 0.0442(5) Uani d . . . 1 . .
H H13 0.3732 1.3133 0.2568 0.053 Uiso calc U . R 1 . .
C C14 0.02238(14) 1.0238(4) 0.38596(8) 0.0303(4) Uani d . . . 1 . .
C C15 0.01008(15) 1.2135(4) 0.42209(8) 0.0341(4) Uani d . . . 1 . .
H H15 0.0558 1.3516 0.4264 0.041 Uiso calc U . R 1 . .
C C16 -0.06991(16) 1.1990(4) 0.45189(9) 0.0374(5) Uani d . . . 1 . .
H H16 -0.0781 1.326 0.4775 0.045 Uiso calc U . R 1 . .
C C17 -0.13732(16) 1.0018(4) 0.44448(9) 0.0385(5) Uani d . . . 1 . .
H H17 -0.1925 0.9941 0.4647 0.046 Uiso calc U . R 1 . .
C C18 -0.12553(16) 0.8146(4) 0.40785(9) 0.0394(5) Uani d . . . 1 . .
H H18 -0.1728 0.6793 0.4027 0.047 Uiso calc U . R 1 . .
C C19 -0.04432(16) 0.8242(4) 0.37841(9) 0.0354(5) Uani d . . . 1 . .
H H19 -0.0351 0.695 0.3535 0.042 Uiso calc U . R 1 . .
N N1 0.21027(12) 0.7974(3) 0.42098(7) 0.0327(4) Uani d . . . 1 . .
N N2 0.10493(12) 1.0394(3) 0.35374(7) 0.0321(4) Uani d . . . 1 . .
O O1 0.00852(12) 1.3314(3) 0.30023(6) 0.0449(4) Uani d . . . 1 . .
S S1 0.29019(4) 0.87159(10) 0.32937(2) 0.03793(19) Uani d . . . 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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 N1 . 1.475(2) ?
C1 C2 . 1.507(3) ?
C1 C3 . 1.517(3) ?
C1 H1 . 1.0 ?
C2 H2A . 0.98 ?
C2 H2B . 0.98 ?
C2 H2C . 0.98 ?
C3 H3A . 0.98 ?
C3 H3B . 0.98 ?
C3 H3C . 0.98 ?
C4 N1 . 1.261(3) ?
C4 N2 . 1.420(2) ?
C4 S1 . 1.7771(18) ?
C5 C6 . 1.506(3) ?
C5 C8 . 1.518(3) ?
C5 S1 . 1.822(2) ?
C5 H5 . 1.0 ?
C6 C7 . 1.506(3) ?
C6 H6A . 0.99 ?
C6 H6B . 0.99 ?
C7 O1 . 1.218(2) ?
C7 N2 . 1.389(3) ?
C8 C9 . 1.384(3) ?
C8 C13 . 1.387(3) ?
C9 C10 . 1.390(3) ?
C9 H9 . 0.95 ?
C10 C11 . 1.371(4) ?
C10 H10 . 0.95 ?
C11 C12 . 1.375(4) ?
C11 H11 . 0.95 ?
C12 C13 . 1.386(3) ?
C12 H12 . 0.95 ?
C13 H13 . 0.95 ?
C14 C19 . 1.377(3) ?
C14 C15 . 1.384(3) ?
C14 N2 . 1.455(2) ?
C15 C16 . 1.386(3) ?
C15 H15 . 0.95 ?
C16 C17 . 1.373(3) ?
C16 H16 . 0.95 ?
C17 C18 . 1.380(3) ?
C17 H17 . 0.95 ?
C18 C19 . 1.393(3) ?
C18 H18 . 0.95 ?
C19 H19 . 0.95 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N1 C1 C2 . . 109.99(17) ?
N1 C1 C3 . . 108.91(16) ?
C2 C1 C3 . . 110.17(18) ?
N1 C1 H1 . . 109.3 ?
C2 C1 H1 . . 109.3 ?
C3 C1 H1 . . 109.3 ?
C1 C2 H2A . . 109.5 ?
C1 C2 H2B . . 109.5 ?
H2A C2 H2B . . 109.5 ?
C1 C2 H2C . . 109.5 ?
H2A C2 H2C . . 109.5 ?
H2B C2 H2C . . 109.5 ?
C1 C3 H3A . . 109.5 ?
C1 C3 H3B . . 109.5 ?
H3A C3 H3B . . 109.5 ?
C1 C3 H3C . . 109.5 ?
H3A C3 H3C . . 109.5 ?
H3B C3 H3C . . 109.5 ?
N1 C4 N2 . . 119.32(16) ?
N1 C4 S1 . . 122.32(14) ?
N2 C4 S1 . . 118.36(14) ?
C6 C5 C8 . . 114.99(17) ?
C6 C5 S1 . . 107.94(14) ?
C8 C5 S1 . . 106.88(12) ?
C6 C5 H5 . . 109.0 ?
C8 C5 H5 . . 109.0 ?
S1 C5 H5 . . 109.0 ?
C5 C6 C7 . . 112.96(17) ?
C5 C6 H6A . . 109.0 ?
C7 C6 H6A . . 109.0 ?
C5 C6 H6B . . 109.0 ?
C7 C6 H6B . . 109.0 ?
H6A C6 H6B . . 107.8 ?
O1 C7 N2 . . 120.13(18) ?
O1 C7 C6 . . 120.68(18) ?
N2 C7 C6 . . 119.19(16) ?
C9 C8 C13 . . 119.51(19) ?
C9 C8 C5 . . 118.97(18) ?
C13 C8 C5 . . 121.51(18) ?
C8 C9 C10 . . 119.9(2) ?
C8 C9 H9 . . 120.1 ?
C10 C9 H9 . . 120.1 ?
C11 C10 C9 . . 120.3(2) ?
C11 C10 H10 . . 119.8 ?
C9 C10 H10 . . 119.8 ?
C10 C11 C12 . . 120.1(2) ?
C10 C11 H11 . . 120.0 ?
C12 C11 H11 . . 120.0 ?
C11 C12 C13 . . 120.2(2) ?
C11 C12 H12 . . 119.9 ?
C13 C12 H12 . . 119.9 ?
C12 C13 C8 . . 120.0(2) ?
C12 C13 H13 . . 120.0 ?
C8 C13 H13 . . 120.0 ?
C19 C14 C15 . . 121.27(18) ?
C19 C14 N2 . . 119.25(17) ?
C15 C14 N2 . . 119.45(17) ?
C14 C15 C16 . . 119.05(19) ?
C14 C15 H15 . . 120.5 ?
C16 C15 H15 . . 120.5 ?
C17 C16 C15 . . 120.24(19) ?
C17 C16 H16 . . 119.9 ?
C15 C16 H16 . . 119.9 ?
C16 C17 C18 . . 120.46(18) ?
C16 C17 H17 . . 119.8 ?
C18 C17 H17 . . 119.8 ?
C17 C18 C19 . . 119.98(19) ?
C17 C18 H18 . . 120.0 ?
C19 C18 H18 . . 120.0 ?
C14 C19 C18 . . 118.98(18) ?
C14 C19 H19 . . 120.5 ?
C18 C19 H19 . . 120.5 ?
C4 N1 C1 . . 119.51(16) ?
C7 N2 C4 . . 126.97(16) ?
C7 N2 C14 . . 115.86(15) ?
C4 N2 C14 . . 116.94(15) ?
C4 S1 C5 . . 102.31(9) ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C8 C5 C6 C7 . . . . 175.76(16) ?
S1 C5 C6 C7 . . . . -65.06(19) ?
C5 C6 C7 O1 . . . . -141.3(2) ?
C5 C6 C7 N2 . . . . 38.7(3) ?
C6 C5 C8 C9 . . . . -137.4(2) ?
S1 C5 C8 C9 . . . . 102.82(18) ?
C6 C5 C8 C13 . . . . 43.8(3) ?
S1 C5 C8 C13 . . . . -75.9(2) ?
C13 C8 C9 C10 . . . . 0.1(3) ?
C5 C8 C9 C10 . . . . -178.68(19) ?
C8 C9 C10 C11 . . . . -0.3(3) ?
C9 C10 C11 C12 . . . . -0.2(4) ?
C10 C11 C12 C13 . . . . 0.8(4) ?
C11 C12 C13 C8 . . . . -1.0(4) ?
C9 C8 C13 C12 . . . . 0.5(3) ?
C5 C8 C13 C12 . . . . 179.3(2) ?
C19 C14 C15 C16 . . . . 1.2(3) ?
N2 C14 C15 C16 . . . . 178.89(17) ?
C14 C15 C16 C17 . . . . -1.6(3) ?
C15 C16 C17 C18 . . . . 0.8(3) ?
C16 C17 C18 C19 . . . . 0.5(3) ?
C15 C14 C19 C18 . . . . 0.0(3) ?
N2 C14 C19 C18 . . . . -177.69(17) ?
C17 C18 C19 C14 . . . . -0.9(3) ?
N2 C4 N1 C1 . . . . -179.85(17) ?
S1 C4 N1 C1 . . . . -0.3(3) ?
C2 C1 N1 C4 . . . . 85.2(2) ?
C3 C1 N1 C4 . . . . -154.02(19) ?
O1 C7 N2 C4 . . . . -174.02(19) ?
C6 C7 N2 C4 . . . . 6.0(3) ?
O1 C7 N2 C14 . . . . 0.3(3) ?
C6 C7 N2 C14 . . . . -179.67(17) ?
N1 C4 N2 C7 . . . . 163.71(19) ?
S1 C4 N2 C7 . . . . -15.8(3) ?
N1 C4 N2 C14 . . . . -10.6(3) ?
S1 C4 N2 C14 . . . . 169.89(13) ?
C19 C14 N2 C7 . . . . 105.2(2) ?
C15 C14 N2 C7 . . . . -72.6(2) ?
C19 C14 N2 C4 . . . . -79.9(2) ?
C15 C14 N2 C4 . . . . 102.4(2) ?
N1 C4 S1 C5 . . . . 168.24(17) ?
N2 C4 S1 C5 . . . . -12.22(17) ?
C6 C5 S1 C4 . . . . 49.24(15) ?
C8 C5 S1 C4 . . . . 173.45(13) ?


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: CHCl3 and Hexane'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_I_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 1859357'
_audit_update_record             
;
2018-07-31 deposited with the CCDC.
2018-10-03 downloaded from the CCDC.
;
_chemical_name_systematic        
N-Phenyl-N'-ethyl-5-benzyl-2-iminothiazolidin-4-one
_chemical_name_common            4g
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H18 N2 O S'
_chemical_formula_iupac          ?
_chemical_formula_weight         310.40

_chemical_melting_point          64-65

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
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                   34.665(4)
_cell_length_b                   6.9265(9)
_cell_length_c                   14.4146(18)
_cell_angle_alpha                90
_cell_angle_beta                 113.1370(10)
_cell_angle_gamma                90
_cell_volume                     3182.7(7)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    6451
_cell_measurement_theta_min      2.5558
_cell_measurement_theta_max      27.5219
_cell_measurement_temperature    173

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.500
_exptl_crystal_size_min          0.100
_exptl_crystal_density_diffrn    1.296
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1312

_exptl_absorpt_coefficient_mu    0.207
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'SADABS (Sheldrick 1996)'
_exptl_absorpt_correction_T_min  0.92
_exptl_absorpt_correction_T_max  0.98

_exptl_special_details           'SADABS (Sheldrick 1996)'

_diffrn_ambient_temperature      173

_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              ?

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'Bruker APEXII CCD area detector'
_diffrn_measurement_method       'Phi and Omega scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            17622
_diffrn_reflns_av_R_equivalents  0.0236
_diffrn_reflns_av_unetI/netI     0.0187
_diffrn_reflns_theta_min         1.28
_diffrn_reflns_theta_max         27.56
_diffrn_reflns_theta_full        27.56
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_limit_h_min       -44
_diffrn_reflns_limit_h_max       44
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18

_refine_special_details          
;
;

_reflns_number_total             3651
_reflns_number_gt                3146
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0380
_refine_ls_R_factor_gt           0.0310
_refine_ls_wR_factor_gt          0.0789
_refine_ls_wR_factor_ref         0.0871
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.042
_refine_ls_number_reflns         3651
_refine_ls_number_parameters     200
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0425P)²+1.8182P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap

_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.247
_refine_diff_density_min         -0.181
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'

_computing_data_collection       'APEX2 (Bruker AXS, 2006)'
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'XSHEL (Bruker AXS,2002)'
_computing_publication_material  'XCIF (Bruker AXS, 2001)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.61186(4) 0.30800(18) 0.56521(10) 0.0271(3) Uani d . . . 1 . .
H H1 0.6172 0.1817 0.5388 0.033 Uiso calc U . R 1 . .
C C2 0.60398(4) 0.27072(18) 0.66201(10) 0.0314(3) Uani d . . . 1 . .
H H2A 0.578 0.1941 0.6445 0.038 Uiso calc U . R 1 . .
H H2B 0.6275 0.1935 0.7096 0.038 Uiso calc U . R 1 . .
C C3 0.59991(4) 0.45436(18) 0.71334(9) 0.0270(3) Uani d . . . 1 . .
C C4 0.63447(4) 0.5294(2) 0.79261(10) 0.0347(3) Uani d . . . 1 . .
H H4 0.66 0.4588 0.8174 0.042 Uiso calc U . R 1 . .
C C5 0.63221(5) 0.7048(2) 0.83578(11) 0.0433(4) Uani d . . . 1 . .
H H5 0.6562 0.7552 0.889 0.052 Uiso calc U . R 1 . .
C C6 0.59502(6) 0.8067(2) 0.80151(12) 0.0476(4) Uani d . . . 1 . .
H H6 0.5934 0.9275 0.8309 0.057 Uiso calc U . R 1 . .
C C7 0.56007(5) 0.7323(2) 0.72420(11) 0.0438(4) Uani d . . . 1 . .
H H7 0.5343 0.8013 0.7012 0.053 Uiso calc U . R 1 . .
C C8 0.56251(4) 0.5574(2) 0.68025(10) 0.0328(3) Uani d . . . 1 . .
H H8 0.5384 0.5074 0.627 0.039 Uiso calc U . R 1 . .
C C9 0.57377(4) 0.40280(18) 0.48495(9) 0.0257(3) Uani d . . . 1 . .
C C10 0.62349(4) 0.64739(18) 0.50538(9) 0.0248(2) Uani d . . . 1 . .
C C11 0.54979(4) 0.69779(19) 0.38239(10) 0.0307(3) Uani d . . . 1 . .
H H11A 0.528 0.6113 0.3359 0.037 Uiso calc U . R 1 . .
H H11B 0.5622 0.7717 0.3421 0.037 Uiso calc U . R 1 . .
C C12 0.52944(5) 0.8367(2) 0.43033(12) 0.0423(4) Uani d . . . 1 . .
H H12A 0.5164 0.7641 0.4687 0.063 Uiso calc U . R 1 . .
H H12B 0.508 0.9121 0.3776 0.063 Uiso calc U . R 1 . .
H H12C 0.5508 0.924 0.4758 0.063 Uiso calc U . R 1 . .
C C13 0.67518(4) 0.88318(18) 0.54491(10) 0.0303(3) Uani d . . . 1 . .
C C14 0.68724(4) 0.9318(2) 0.64602(11) 0.0364(3) Uani d . . . 1 . .
H H14 0.6692 0.9044 0.6797 0.044 Uiso calc U . R 1 . .
C C15 0.72571(5) 1.0203(2) 0.69790(13) 0.0456(4) Uani d . . . 1 . .
H H15 0.7337 1.0546 0.7668 0.055 Uiso calc U . R 1 . .
C C16 0.75229(5) 1.0587(2) 0.65030(14) 0.0495(4) Uani d . . . 1 . .
H H16 0.7784 1.1206 0.6859 0.059 Uiso calc U . R 1 . .
C C17 0.74092(5) 1.0072(2) 0.55083(15) 0.0487(4) Uani d . . . 1 . .
H H17 0.7596 1.0311 0.5184 0.058 Uiso calc U . R 1 . .
C C18 0.70227(4) 0.9203(2) 0.49746(12) 0.0392(3) Uani d . . . 1 . .
H H18 0.6945 0.8866 0.4286 0.047 Uiso calc U . R 1 . .
N N1 0.58260(3) 0.58062(15) 0.45720(8) 0.0248(2) Uani d . . . 1 . .
N N2 0.63397(3) 0.81464(16) 0.48812(8) 0.0306(2) Uani d . . . 1 . .
O O1 0.53916(3) 0.32973(13) 0.45179(7) 0.0341(2) Uani d . . . 1 . .
S S1 0.65602(2) 0.46808(5) 0.58511(2) 0.02788(10) Uani d . . . 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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C9 . 1.5207(17) ?
C1 C2 . 1.5452(18) ?
C1 S1 . 1.8196(13) ?
C1 H1 . 1.0 ?
C2 C3 . 1.5057(18) ?
C2 H2A . 0.99 ?
C2 H2B . 0.99 ?
C3 C8 . 1.3899(18) ?
C3 C4 . 1.3910(18) ?
C4 C5 . 1.381(2) ?
C4 H4 . 0.95 ?
C5 C6 . 1.380(2) ?
C5 H5 . 0.95 ?
C6 C7 . 1.384(2) ?
C6 H6 . 0.95 ?
C7 C8 . 1.385(2) ?
C7 H7 . 0.95 ?
C8 H8 . 0.95 ?
C9 O1 . 1.2138(15) ?
C9 N1 . 1.3663(16) ?
C10 N2 . 1.2677(16) ?
C10 N1 . 1.3899(15) ?
C10 S1 . 1.7654(12) ?
C11 N1 . 1.4667(15) ?
C11 C12 . 1.511(2) ?
C11 H11A . 0.99 ?
C11 H11B . 0.99 ?
C12 H12A . 0.98 ?
C12 H12B . 0.98 ?
C12 H12C . 0.98 ?
C13 C18 . 1.386(2) ?
C13 C14 . 1.391(2) ?
C13 N2 . 1.4203(16) ?
C14 C15 . 1.389(2) ?
C14 H14 . 0.95 ?
C15 C16 . 1.374(2) ?
C15 H15 . 0.95 ?
C16 C17 . 1.376(3) ?
C16 H16 . 0.95 ?
C17 C18 . 1.393(2) ?
C17 H17 . 0.95 ?
C18 H18 . 0.95 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C9 C1 C2 . . 110.52(10) ?
C9 C1 S1 . . 106.38(8) ?
C2 C1 S1 . . 113.31(9) ?
C9 C1 H1 . . 108.8 ?
C2 C1 H1 . . 108.8 ?
S1 C1 H1 . . 108.8 ?
C3 C2 C1 . . 112.73(10) ?
C3 C2 H2A . . 109.0 ?
C1 C2 H2A . . 109.0 ?
C3 C2 H2B . . 109.0 ?
C1 C2 H2B . . 109.0 ?
H2A C2 H2B . . 107.8 ?
C8 C3 C4 . . 118.45(13) ?
C8 C3 C2 . . 121.32(12) ?
C4 C3 C2 . . 120.16(12) ?
C5 C4 C3 . . 121.03(14) ?
C5 C4 H4 . . 119.5 ?
C3 C4 H4 . . 119.5 ?
C4 C5 C6 . . 119.94(14) ?
C4 C5 H5 . . 120.0 ?
C6 C5 H5 . . 120.0 ?
C5 C6 C7 . . 119.81(14) ?
C5 C6 H6 . . 120.1 ?
C7 C6 H6 . . 120.1 ?
C6 C7 C8 . . 120.17(14) ?
C6 C7 H7 . . 119.9 ?
C8 C7 H7 . . 119.9 ?
C7 C8 C3 . . 120.56(13) ?
C7 C8 H8 . . 119.7 ?
C3 C8 H8 . . 119.7 ?
O1 C9 N1 . . 124.13(11) ?
O1 C9 C1 . . 123.22(11) ?
N1 C9 C1 . . 112.61(10) ?
N2 C10 N1 . . 121.38(11) ?
N2 C10 S1 . . 127.71(10) ?
N1 C10 S1 . . 110.88(9) ?
N1 C11 C12 . . 112.49(11) ?
N1 C11 H11A . . 109.1 ?
C12 C11 H11A . . 109.1 ?
N1 C11 H11B . . 109.1 ?
C12 C11 H11B . . 109.1 ?
H11A C11 H11B . . 107.8 ?
C11 C12 H12A . . 109.5 ?
C11 C12 H12B . . 109.5 ?
H12A C12 H12B . . 109.5 ?
C11 C12 H12C . . 109.5 ?
H12A C12 H12C . . 109.5 ?
H12B C12 H12C . . 109.5 ?
C18 C13 C14 . . 119.30(13) ?
C18 C13 N2 . . 120.05(13) ?
C14 C13 N2 . . 120.35(12) ?
C15 C14 C13 . . 120.06(14) ?
C15 C14 H14 . . 120.0 ?
C13 C14 H14 . . 120.0 ?
C16 C15 C14 . . 120.46(15) ?
C16 C15 H15 . . 119.8 ?
C14 C15 H15 . . 119.8 ?
C15 C16 C17 . . 119.77(14) ?
C15 C16 H16 . . 120.1 ?
C17 C16 H16 . . 120.1 ?
C16 C17 C18 . . 120.46(15) ?
C16 C17 H17 . . 119.8 ?
C18 C17 H17 . . 119.8 ?
C13 C18 C17 . . 119.94(15) ?
C13 C18 H18 . . 120.0 ?
C17 C18 H18 . . 120.0 ?
C9 N1 C10 . . 117.09(10) ?
C9 N1 C11 . . 121.05(10) ?
C10 N1 C11 . . 121.82(10) ?
C10 N2 C13 . . 119.55(11) ?
C10 S1 C1 . . 92.48(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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C9 C1 C2 C3 . . . . -66.29(14) ?
S1 C1 C2 C3 . . . . 53.00(13) ?
C1 C2 C3 C8 . . . . 80.91(15) ?
C1 C2 C3 C4 . . . . -96.08(14) ?
C8 C3 C4 C5 . . . . -1.87(19) ?
C2 C3 C4 C5 . . . . 175.21(12) ?
C3 C4 C5 C6 . . . . 1.2(2) ?
C4 C5 C6 C7 . . . . 0.2(2) ?
C5 C6 C7 C8 . . . . -0.9(2) ?
C6 C7 C8 C3 . . . . 0.2(2) ?
C4 C3 C8 C7 . . . . 1.2(2) ?
C2 C3 C8 C7 . . . . -175.88(12) ?
C2 C1 C9 O1 . . . . -58.95(16) ?
S1 C1 C9 O1 . . . . 177.66(10) ?
C2 C1 C9 N1 . . . . 119.03(11) ?
S1 C1 C9 N1 . . . . -4.36(12) ?
C18 C13 C14 C15 . . . . 1.4(2) ?
N2 C13 C14 C15 . . . . -172.24(13) ?
C13 C14 C15 C16 . . . . -0.7(2) ?
C14 C15 C16 C17 . . . . -0.7(2) ?
C15 C16 C17 C18 . . . . 1.4(3) ?
C14 C13 C18 C17 . . . . -0.6(2) ?
N2 C13 C18 C17 . . . . 172.98(13) ?
C16 C17 C18 C13 . . . . -0.8(2) ?
O1 C9 N1 C10 . . . . 177.31(12) ?
C1 C9 N1 C10 . . . . -0.65(15) ?
O1 C9 N1 C11 . . . . -0.57(19) ?
C1 C9 N1 C11 . . . . -178.53(11) ?
N2 C10 N1 C9 . . . . -176.38(11) ?
S1 C10 N1 C9 . . . . 5.63(13) ?
N2 C10 N1 C11 . . . . 1.48(18) ?
S1 C10 N1 C11 . . . . -176.51(9) ?
C12 C11 N1 C9 . . . . 93.22(14) ?
C12 C11 N1 C10 . . . . -84.56(14) ?
N1 C10 N2 C13 . . . . 174.88(11) ?
S1 C10 N2 C13 . . . . -7.49(19) ?
C18 C13 N2 C10 . . . . 115.29(15) ?
C14 C13 N2 C10 . . . . -71.16(17) ?
N2 C10 S1 C1 . . . . 175.31(12) ?
N1 C10 S1 C1 . . . . -6.87(9) ?
C9 C1 S1 C10 . . . . 6.21(9) ?
C2 C1 S1 C10 . . . . -115.42(9) ?


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: CHCl3 and Hexane'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_I_CCDC3
_database_code_depnum_ccdc_archive 'CCDC 1859359'
_audit_update_record             
;
2018-08-01 deposited with the CCDC.
2018-10-03 downloaded from the CCDC.
;
_chemical_name_systematic        
5-Benzyl-5-hydroxy-1,3-diisopropyl-2-thioxoimidazolidin-4-one
_chemical_name_common            5c
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H22 N2 O2 S'
_chemical_formula_iupac          ?
_chemical_formula_weight         306.41

_chemical_melting_point          90-92

_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.7745(14)
_cell_length_b                   9.4352(16)
_cell_length_c                   20.409(3)
_cell_angle_alpha                93.504(2)
_cell_angle_beta                 97.479(2)
_cell_angle_gamma                90.918(2)
_cell_volume                     1671.6(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1794
_cell_measurement_theta_min      2.1636
_cell_measurement_theta_max      23.5081
_cell_measurement_temperature    173

_exptl_crystal_description       block
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.100
_exptl_crystal_density_diffrn    1.218
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             656

_exptl_absorpt_coefficient_mu    0.200
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'SADABS (Sheldrick 1996)'
_exptl_absorpt_correction_T_min  0.89
_exptl_absorpt_correction_T_max  0.98

_exptl_special_details           'SADABS (Sheldrick 1996)'

_diffrn_ambient_temperature      173

_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              ?

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'Bruker APEXII CCD area detector'
_diffrn_measurement_method       'Phi and Omega scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            9602
_diffrn_reflns_av_R_equivalents  0.0264
_diffrn_reflns_av_unetI/netI     0.0684
_diffrn_reflns_theta_min         1.01
_diffrn_reflns_theta_max         27.57
_diffrn_reflns_theta_full        27.57
_diffrn_measured_fraction_theta_max 0.944
_diffrn_measured_fraction_theta_full 0.944
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       26

_refine_special_details          
;
;

_reflns_number_total             7319
_reflns_number_gt                4764
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0851
_refine_ls_R_factor_gt           0.0538
_refine_ls_wR_factor_gt          0.1302
_refine_ls_wR_factor_ref         0.1602
_refine_ls_goodness_of_fit_ref   0.999
_refine_ls_restrained_S_all      0.999
_refine_ls_number_reflns         7319
_refine_ls_number_parameters     385
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0758P)²] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     difmap
_atom_sites_solution_secondary   direct

_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.280
_refine_diff_density_min         -0.275
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'

_computing_data_collection       'APEX2 (Bruker AXS, 2006)'
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'XSHEL (Bruker AXS,2002)'
_computing_publication_material  'XCIF (Bruker AXS, 2001)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.0708(3) 0.2751(2) 0.49816(11) 0.0283(5) Uani d . . . 1 . .
C C2 0.2591(2) 0.4058(2) 0.46122(11) 0.0268(5) Uani d . . . 1 . .
C C3 0.3333(2) 0.3272(2) 0.51970(11) 0.0273(5) Uani d . . . 1 . .
C C4 -0.0027(3) 0.4198(3) 0.39868(12) 0.0326(5) Uani d . . . 1 . .
H H4A 0.0359 0.5113 0.3851 0.039 Uiso calc U . R 1 . .
H H4B -0.102 0.4372 0.4156 0.039 Uiso calc U . R 1 . .
C C5 -0.0291(4) 0.3150(3) 0.33871(14) 0.0525(8) Uani d . . . 1 . .
H H5A -0.0683 0.2233 0.3518 0.063 Uiso calc U . R 1 . .
H H5B 0.0694 0.2979 0.3212 0.063 Uiso calc U . R 1 . .
C C6 -0.1451(4) 0.3728(4) 0.28487(15) 0.0748(11) Uani d . . . 1 . .
H H6A -0.2389 0.399 0.3036 0.112 Uiso calc U . R 1 . .
H H6B -0.1703 0.2997 0.2487 0.112 Uiso calc U . R 1 . .
H H6C -0.1005 0.4567 0.2678 0.112 Uiso calc U . R 1 . .
C C7 0.2098(3) 0.1559(3) 0.59267(12) 0.0350(6) Uani d . . . 1 . .
H H7A 0.3145 0.1176 0.6005 0.042 Uiso calc U . R 1 . .
H H7B 0.1367 0.0745 0.5808 0.042 Uiso calc U . R 1 . .
C C8 0.1734(3) 0.2313(3) 0.65609(13) 0.0459(7) Uani d . . . 1 . .
H H8A 0.2461 0.3129 0.6682 0.055 Uiso calc U . R 1 . .
H H8B 0.0682 0.2688 0.6488 0.055 Uiso calc U . R 1 . .
C C9 0.1844(4) 0.1341(4) 0.71233(15) 0.0678(10) Uani d . . . 1 . .
H H9A 0.1127 0.0532 0.7005 0.102 Uiso calc U . R 1 . .
H H9B 0.1581 0.1862 0.7522 0.102 Uiso calc U . R 1 . .
H H9C 0.2895 0.0998 0.7209 0.102 Uiso calc U . R 1 . .
C C10 0.4641(2) 0.2337(3) 0.50028(12) 0.0316(5) Uani d . . . 1 . .
H H10A 0.5569 0.2948 0.5001 0.038 Uiso calc U . R 1 . .
H H10B 0.4885 0.1648 0.5346 0.038 Uiso calc U . R 1 . .
C C11 0.4296(3) 0.1533(2) 0.43393(12) 0.0298(5) Uani d . . . 1 . .
C C12 0.3142(3) 0.0491(3) 0.42135(14) 0.0386(6) Uani d . . . 1 . .
H H12 0.2557 0.0266 0.4555 0.046 Uiso calc U . R 1 . .
C C13 0.2831(3) -0.0228(3) 0.35947(15) 0.0505(7) Uani d . . . 1 . .
H H13 0.2031 -0.0931 0.3515 0.061 Uiso calc U . R 1 . .
C C14 0.3676(4) 0.0073(3) 0.30963(15) 0.0522(8) Uani d . . . 1 . .
H H14 0.3465 -0.0419 0.2673 0.063 Uiso calc U . R 1 . .
C C15 0.4836(3) 0.1100(3) 0.32190(14) 0.0474(7) Uani d . . . 1 . .
H H15 0.5429 0.1312 0.2878 0.057 Uiso calc U . R 1 . .
C C16 0.5138(3) 0.1817(3) 0.38304(13) 0.0373(6) Uani d . . . 1 . .
H H16 0.5939 0.252 0.3906 0.045 Uiso calc U . R 1 . .
C C17 0.2548(3) 0.8733(3) 0.08923(11) 0.0317(5) Uani d . . . 1 . .
C C18 0.0656(2) 0.6936(2) 0.06929(11) 0.0285(5) Uani d . . . 1 . .
C C19 0.2142(3) 0.6482(3) 0.04283(11) 0.0303(5) Uani d . . . 1 . .
C C20 0.4743(3) 0.7557(3) 0.03842(13) 0.0428(7) Uani d . . . 1 . .
H H20A 0.4966 0.8473 0.02 0.051 Uiso calc U . R 1 . .
H H20B 0.4801 0.6793 0.0034 0.051 Uiso calc U . R 1 . .
C C21 0.5957(3) 0.7323(4) 0.09693(17) 0.0583(9) Uani d . . . 1 . .
H H21A 0.6983 0.7367 0.0819 0.07 Uiso calc U . R 1 . .
H H21B 0.5917 0.811 0.131 0.07 Uiso calc U . R 1 . .
C C22 0.5786(4) 0.5955(4) 0.12793(19) 0.0746(10) Uani d . . . 1 . .
H H22A 0.4769 0.5893 0.1426 0.112 Uiso calc U . R 1 . .
H H22B 0.6582 0.5904 0.1661 0.112 Uiso calc U . R 1 . .
H H22C 0.5896 0.5165 0.0955 0.112 Uiso calc U . R 1 . .
C C23 0.0059(3) 0.9315(3) 0.12783(12) 0.0357(6) Uani d . . . 1 . .
H H23A 0.0651 0.9887 0.1652 0.043 Uiso calc U . R 1 . .
H H23B -0.0717 0.8737 0.1462 0.043 Uiso calc U . R 1 . .
C C24 -0.0771(3) 1.0315(3) 0.08054(13) 0.0421(6) Uani d . . . 1 . .
H H24A -0.0009 1.0862 0.0599 0.05 Uiso calc U . R 1 . .
H H24B -0.1436 0.9757 0.0449 0.05 Uiso calc U . R 1 . .
C C25 -0.1744(4) 1.1332(3) 0.11672(16) 0.0620(9) Uani d . . . 1 . .
H H25A -0.2519 1.0792 0.1361 0.093 Uiso calc U . R 1 . .
H H25B -0.2257 1.1977 0.0855 0.093 Uiso calc U . R 1 . .
H H25C -0.1086 1.1885 0.152 0.093 Uiso calc U . R 1 . .
C C26 0.0174(3) 0.5921(3) 0.11884(12) 0.0344(6) Uani d . . . 1 . .
H H26A -0.0661 0.6362 0.1406 0.041 Uiso calc U . R 1 . .
H H26B -0.0257 0.504 0.094 0.041 Uiso calc U . R 1 . .
C C27 0.1428(3) 0.5519(3) 0.17204(12) 0.0329(5) Uani d . . . 1 . .
C C28 0.1944(3) 0.6440(3) 0.22586(13) 0.0424(6) Uani d . . . 1 . .
H H28 0.1515 0.7354 0.2295 0.051 Uiso calc U . R 1 . .
C C29 0.3082(4) 0.6047(3) 0.27462(14) 0.0535(8) Uani d . . . 1 . .
H H29 0.3426 0.6693 0.3113 0.064 Uiso calc U . R 1 . .
C C30 0.3713(4) 0.4730(3) 0.27015(14) 0.0587(8) Uani d . . . 1 . .
H H30 0.4491 0.446 0.3036 0.07 Uiso calc U . R 1 . .
C C31 0.3205(4) 0.3798(3) 0.21649(14) 0.0570(8) Uani d . . . 1 . .
H H31 0.3638 0.2884 0.2129 0.068 Uiso calc U . R 1 . .
C C32 0.2066(3) 0.4194(3) 0.16797(13) 0.0470(7) Uani d . . . 1 . .
H H32 0.172 0.3546 0.1314 0.056 Uiso calc U . R 1 . .
N N1 0.1068(2) 0.36944(19) 0.45175(9) 0.0267(4) Uani d . . . 1 . .
N N2 0.2015(2) 0.2472(2) 0.53685(9) 0.0290(4) Uani d . . . 1 . .
N N3 0.3178(2) 0.7571(2) 0.05688(10) 0.0326(5) Uani d . . . 1 . .
N N4 0.1109(2) 0.8358(2) 0.09781(9) 0.0303(4) Uani d . . . 1 . .
O O1 0.32267(18) 0.48709(17) 0.42930(8) 0.0334(4) Uani d . . . 1 . .
O O2 0.38411(18) 0.42236(17) 0.57443(8) 0.0343(4) Uani d . . . 1 . .
H H2 0.4712 0.4561 0.5702 0.051 Uiso calc U . R 1 . .
O O3 0.23341(19) 0.53534(18) 0.01286(9) 0.0396(4) Uani d . . . 1 . .
O O4 -0.05187(18) 0.70693(18) 0.01625(8) 0.0372(4) Uani d . . . 1 . .
H H4 -0.1026 0.6301 0.0087 0.056 Uiso calc U . R 1 . .
S S1 -0.10416(7) 0.21512(7) 0.50337(4) 0.0424(2) Uani d . . . 1 . .
S S2 0.34542(8) 1.02610(8) 0.11119(4) 0.0495(2) Uani d . . . 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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 N2 . 1.345(3) ?
C1 N1 . 1.400(3) ?
C1 S1 . 1.646(2) ?
C2 O1 . 1.211(3) ?
C2 N1 . 1.360(3) ?
C2 C3 . 1.524(3) ?
C3 O2 . 1.410(3) ?
C3 N2 . 1.462(3) ?
C3 C10 . 1.536(3) ?
C4 N1 . 1.459(3) ?
C4 C5 . 1.517(3) ?
C4 H4A . 0.99 ?
C4 H4B . 0.99 ?
C5 C6 . 1.530(4) ?
C5 H5A . 0.99 ?
C5 H5B . 0.99 ?
C6 H6A . 0.98 ?
C6 H6B . 0.98 ?
C6 H6C . 0.98 ?
C7 N2 . 1.465(3) ?
C7 C8 . 1.512(3) ?
C7 H7A . 0.99 ?
C7 H7B . 0.99 ?
C8 C9 . 1.507(4) ?
C8 H8A . 0.99 ?
C8 H8B . 0.99 ?
C9 H9A . 0.98 ?
C9 H9B . 0.98 ?
C9 H9C . 0.98 ?
C10 C11 . 1.504(3) ?
C10 H10A . 0.99 ?
C10 H10B . 0.99 ?
C11 C16 . 1.387(3) ?
C11 C12 . 1.389(3) ?
C12 C13 . 1.389(4) ?
C12 H12 . 0.95 ?
C13 C14 . 1.375(4) ?
C13 H13 . 0.95 ?
C14 C15 . 1.382(4) ?
C14 H14 . 0.95 ?
C15 C16 . 1.375(4) ?
C15 H15 . 0.95 ?
C16 H16 . 0.95 ?
C17 N4 . 1.342(3) ?
C17 N3 . 1.403(3) ?
C17 S2 . 1.644(2) ?
C18 O4 . 1.407(3) ?
C18 N4 . 1.458(3) ?
C18 C26 . 1.528(3) ?
C18 C19 . 1.532(3) ?
C19 O3 . 1.221(3) ?
C19 N3 . 1.353(3) ?
C20 N3 . 1.471(3) ?
C20 C21 . 1.522(4) ?
C20 H20A . 0.99 ?
C20 H20B . 0.99 ?
C21 C22 . 1.486(5) ?
C21 H21A . 0.99 ?
C21 H21B . 0.99 ?
C22 H22A . 0.98 ?
C22 H22B . 0.98 ?
C22 H22C . 0.98 ?
C23 N4 . 1.465(3) ?
C23 C24 . 1.517(4) ?
C23 H23A . 0.99 ?
C23 H23B . 0.99 ?
C24 C25 . 1.516(4) ?
C24 H24A . 0.99 ?
C24 H24B . 0.99 ?
C25 H25A . 0.98 ?
C25 H25B . 0.98 ?
C25 H25C . 0.98 ?
C26 C27 . 1.512(3) ?
C26 H26A . 0.99 ?
C26 H26B . 0.99 ?
C27 C32 . 1.380(3) ?
C27 C28 . 1.381(3) ?
C28 C29 . 1.386(4) ?
C28 H28 . 0.95 ?
C29 C30 . 1.371(4) ?
C29 H29 . 0.95 ?
C30 C31 . 1.384(4) ?
C30 H30 . 0.95 ?
C31 C32 . 1.385(4) ?
C31 H31 . 0.95 ?
C32 H32 . 0.95 ?
O2 H2 . 0.84 ?
O4 H4 . 0.84 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N2 C1 N1 . . 108.08(19) ?
N2 C1 S1 . . 127.68(19) ?
N1 C1 S1 . . 124.23(17) ?
O1 C2 N1 . . 126.0(2) ?
O1 C2 C3 . . 126.7(2) ?
N1 C2 C3 . . 107.35(18) ?
O2 C3 N2 . . 106.93(17) ?
O2 C3 C2 . . 111.13(18) ?
N2 C3 C2 . . 101.39(17) ?
O2 C3 C10 . . 111.53(18) ?
N2 C3 C10 . . 114.02(18) ?
C2 C3 C10 . . 111.38(18) ?
N1 C4 C5 . . 112.5(2) ?
N1 C4 H4A . . 109.1 ?
C5 C4 H4A . . 109.1 ?
N1 C4 H4B . . 109.1 ?
C5 C4 H4B . . 109.1 ?
H4A C4 H4B . . 107.8 ?
C4 C5 C6 . . 110.3(2) ?
C4 C5 H5A . . 109.6 ?
C6 C5 H5A . . 109.6 ?
C4 C5 H5B . . 109.6 ?
C6 C5 H5B . . 109.6 ?
H5A C5 H5B . . 108.1 ?
C5 C6 H6A . . 109.5 ?
C5 C6 H6B . . 109.5 ?
H6A C6 H6B . . 109.5 ?
C5 C6 H6C . . 109.5 ?
H6A C6 H6C . . 109.5 ?
H6B C6 H6C . . 109.5 ?
N2 C7 C8 . . 113.6(2) ?
N2 C7 H7A . . 108.8 ?
C8 C7 H7A . . 108.8 ?
N2 C7 H7B . . 108.8 ?
C8 C7 H7B . . 108.8 ?
H7A C7 H7B . . 107.7 ?
C9 C8 C7 . . 111.9(2) ?
C9 C8 H8A . . 109.2 ?
C7 C8 H8A . . 109.2 ?
C9 C8 H8B . . 109.2 ?
C7 C8 H8B . . 109.2 ?
H8A C8 H8B . . 107.9 ?
C8 C9 H9A . . 109.5 ?
C8 C9 H9B . . 109.5 ?
H9A C9 H9B . . 109.5 ?
C8 C9 H9C . . 109.5 ?
H9A C9 H9C . . 109.5 ?
H9B C9 H9C . . 109.5 ?
C11 C10 C3 . . 114.64(19) ?
C11 C10 H10A . . 108.6 ?
C3 C10 H10A . . 108.6 ?
C11 C10 H10B . . 108.6 ?
C3 C10 H10B . . 108.6 ?
H10A C10 H10B . . 107.6 ?
C16 C11 C12 . . 117.8(2) ?
C16 C11 C10 . . 120.3(2) ?
C12 C11 C10 . . 121.8(2) ?
C11 C12 C13 . . 120.9(2) ?
C11 C12 H12 . . 119.6 ?
C13 C12 H12 . . 119.6 ?
C14 C13 C12 . . 120.4(3) ?
C14 C13 H13 . . 119.8 ?
C12 C13 H13 . . 119.8 ?
C13 C14 C15 . . 119.1(3) ?
C13 C14 H14 . . 120.4 ?
C15 C14 H14 . . 120.4 ?
C16 C15 C14 . . 120.5(3) ?
C16 C15 H15 . . 119.8 ?
C14 C15 H15 . . 119.8 ?
C15 C16 C11 . . 121.3(2) ?
C15 C16 H16 . . 119.4 ?
C11 C16 H16 . . 119.4 ?
N4 C17 N3 . . 107.60(19) ?
N4 C17 S2 . . 127.79(19) ?
N3 C17 S2 . . 124.61(17) ?
O4 C18 N4 . . 107.92(19) ?
O4 C18 C26 . . 111.51(18) ?
N4 C18 C26 . . 114.34(19) ?
O4 C18 C19 . . 109.96(18) ?
N4 C18 C19 . . 100.52(17) ?
C26 C18 C19 . . 112.00(19) ?
O3 C19 N3 . . 126.4(2) ?
O3 C19 C18 . . 125.8(2) ?
N3 C19 C18 . . 107.74(19) ?
N3 C20 C21 . . 112.5(2) ?
N3 C20 H20A . . 109.1 ?
C21 C20 H20A . . 109.1 ?
N3 C20 H20B . . 109.1 ?
C21 C20 H20B . . 109.1 ?
H20A C20 H20B . . 107.8 ?
C22 C21 C20 . . 114.6(3) ?
C22 C21 H21A . . 108.6 ?
C20 C21 H21A . . 108.6 ?
C22 C21 H21B . . 108.6 ?
C20 C21 H21B . . 108.6 ?
H21A C21 H21B . . 107.6 ?
C21 C22 H22A . . 109.5 ?
C21 C22 H22B . . 109.5 ?
H22A C22 H22B . . 109.5 ?
C21 C22 H22C . . 109.5 ?
H22A C22 H22C . . 109.5 ?
H22B C22 H22C . . 109.5 ?
N4 C23 C24 . . 114.3(2) ?
N4 C23 H23A . . 108.7 ?
C24 C23 H23A . . 108.7 ?
N4 C23 H23B . . 108.7 ?
C24 C23 H23B . . 108.7 ?
H23A C23 H23B . . 107.6 ?
C25 C24 C23 . . 110.8(2) ?
C25 C24 H24A . . 109.5 ?
C23 C24 H24A . . 109.5 ?
C25 C24 H24B . . 109.5 ?
C23 C24 H24B . . 109.5 ?
H24A C24 H24B . . 108.1 ?
C24 C25 H25A . . 109.5 ?
C24 C25 H25B . . 109.5 ?
H25A C25 H25B . . 109.5 ?
C24 C25 H25C . . 109.5 ?
H25A C25 H25C . . 109.5 ?
H25B C25 H25C . . 109.5 ?
C27 C26 C18 . . 115.98(19) ?
C27 C26 H26A . . 108.3 ?
C18 C26 H26A . . 108.3 ?
C27 C26 H26B . . 108.3 ?
C18 C26 H26B . . 108.3 ?
H26A C26 H26B . . 107.4 ?
C32 C27 C28 . . 118.4(2) ?
C32 C27 C26 . . 119.9(2) ?
C28 C27 C26 . . 121.7(2) ?
C27 C28 C29 . . 120.9(3) ?
C27 C28 H28 . . 119.6 ?
C29 C28 H28 . . 119.6 ?
C30 C29 C28 . . 120.3(3) ?
C30 C29 H29 . . 119.8 ?
C28 C29 H29 . . 119.8 ?
C29 C30 C31 . . 119.4(3) ?
C29 C30 H30 . . 120.3 ?
C31 C30 H30 . . 120.3 ?
C30 C31 C32 . . 120.1(3) ?
C30 C31 H31 . . 120.0 ?
C32 C31 H31 . . 120.0 ?
C27 C32 C31 . . 120.9(2) ?
C27 C32 H32 . . 119.6 ?
C31 C32 H32 . . 119.6 ?
C2 N1 C1 . . 111.24(18) ?
C2 N1 C4 . . 123.84(19) ?
C1 N1 C4 . . 124.89(18) ?
C1 N2 C3 . . 111.90(19) ?
C1 N2 C7 . . 124.23(19) ?
C3 N2 C7 . . 123.73(19) ?
C19 N3 C17 . . 111.24(19) ?
C19 N3 C20 . . 124.3(2) ?
C17 N3 C20 . . 124.41(19) ?
C17 N4 C18 . . 112.84(19) ?
C17 N4 C23 . . 123.67(19) ?
C18 N4 C23 . . 123.31(18) ?
C3 O2 H2 . . 109.5 ?
C18 O4 H4 . . 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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
O1 C2 C3 O2 . . . . 66.8(3) ?
N1 C2 C3 O2 . . . . -112.47(19) ?
O1 C2 C3 N2 . . . . -179.9(2) ?
N1 C2 C3 N2 . . . . 0.9(2) ?
O1 C2 C3 C10 . . . . -58.2(3) ?
N1 C2 C3 C10 . . . . 122.53(19) ?
N1 C4 C5 C6 . . . . 179.8(2) ?
N2 C7 C8 C9 . . . . -179.6(2) ?
O2 C3 C10 C11 . . . . -166.91(19) ?
N2 C3 C10 C11 . . . . 71.9(3) ?
C2 C3 C10 C11 . . . . -42.1(3) ?
C3 C10 C11 C16 . . . . 115.7(2) ?
C3 C10 C11 C12 . . . . -64.4(3) ?
C16 C11 C12 C13 . . . . -0.8(4) ?
C10 C11 C12 C13 . . . . 179.3(2) ?
C11 C12 C13 C14 . . . . 0.7(4) ?
C12 C13 C14 C15 . . . . -0.1(4) ?
C13 C14 C15 C16 . . . . -0.3(4) ?
C14 C15 C16 C11 . . . . 0.1(4) ?
C12 C11 C16 C15 . . . . 0.5(4) ?
C10 C11 C16 C15 . . . . -179.6(2) ?
O4 C18 C19 O3 . . . . -64.9(3) ?
N4 C18 C19 O3 . . . . -178.5(2) ?
C26 C18 C19 O3 . . . . 59.7(3) ?
O4 C18 C19 N3 . . . . 113.2(2) ?
N4 C18 C19 N3 . . . . -0.4(2) ?
C26 C18 C19 N3 . . . . -122.2(2) ?
N3 C20 C21 C22 . . . . 60.8(3) ?
N4 C23 C24 C25 . . . . -176.0(2) ?
O4 C18 C26 C27 . . . . 170.8(2) ?
N4 C18 C26 C27 . . . . -66.4(3) ?
C19 C18 C26 C27 . . . . 47.1(3) ?
C18 C26 C27 C32 . . . . -104.4(3) ?
C18 C26 C27 C28 . . . . 76.6(3) ?
C32 C27 C28 C29 . . . . 0.2(4) ?
C26 C27 C28 C29 . . . . 179.2(2) ?
C27 C28 C29 C30 . . . . -0.1(5) ?
C28 C29 C30 C31 . . . . 0.1(5) ?
C29 C30 C31 C32 . . . . -0.2(5) ?
C28 C27 C32 C31 . . . . -0.3(4) ?
C26 C27 C32 C31 . . . . -179.3(3) ?
C30 C31 C32 C27 . . . . 0.3(5) ?
O1 C2 N1 C1 . . . . -178.9(2) ?
C3 C2 N1 C1 . . . . 0.4(2) ?
O1 C2 N1 C4 . . . . 2.8(3) ?
C3 C2 N1 C4 . . . . -177.97(19) ?
N2 C1 N1 C2 . . . . -1.6(2) ?
S1 C1 N1 C2 . . . . 177.00(16) ?
N2 C1 N1 C4 . . . . 176.69(19) ?
S1 C1 N1 C4 . . . . -4.7(3) ?
C5 C4 N1 C2 . . . . 96.0(3) ?
C5 C4 N1 C1 . . . . -82.1(3) ?
N1 C1 N2 C3 . . . . 2.3(2) ?
S1 C1 N2 C3 . . . . -176.31(16) ?
N1 C1 N2 C7 . . . . 178.04(19) ?
S1 C1 N2 C7 . . . . -0.5(3) ?
O2 C3 N2 C1 . . . . 114.5(2) ?
C2 C3 N2 C1 . . . . -1.9(2) ?
C10 C3 N2 C1 . . . . -121.7(2) ?
O2 C3 N2 C7 . . . . -61.3(3) ?
C2 C3 N2 C7 . . . . -177.73(19) ?
C10 C3 N2 C7 . . . . 62.5(3) ?
C8 C7 N2 C1 . . . . -83.4(3) ?
C8 C7 N2 C3 . . . . 91.9(3) ?
O3 C19 N3 C17 . . . . 177.1(2) ?
C18 C19 N3 C17 . . . . -1.0(3) ?
O3 C19 N3 C20 . . . . -0.8(4) ?
C18 C19 N3 C20 . . . . -178.9(2) ?
N4 C17 N3 C19 . . . . 2.1(3) ?
S2 C17 N3 C19 . . . . -177.57(19) ?
N4 C17 N3 C20 . . . . 180.0(2) ?
S2 C17 N3 C20 . . . . 0.4(3) ?
C21 C20 N3 C19 . . . . -103.7(3) ?
C21 C20 N3 C17 . . . . 78.6(3) ?
N3 C17 N4 C18 . . . . -2.3(3) ?
S2 C17 N4 C18 . . . . 177.27(19) ?
N3 C17 N4 C23 . . . . -177.7(2) ?
S2 C17 N4 C23 . . . . 1.9(4) ?
O4 C18 N4 C17 . . . . -113.5(2) ?
C26 C18 N4 C17 . . . . 121.8(2) ?
C19 C18 N4 C17 . . . . 1.7(2) ?
O4 C18 N4 C23 . . . . 61.9(3) ?
C26 C18 N4 C23 . . . . -62.8(3) ?
C19 C18 N4 C23 . . . . 177.0(2) ?
C24 C23 N4 C17 . . . . 82.3(3) ?
C24 C23 N4 C18 . . . . -92.5(3) ?


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: CHCl3 and Hexane'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_I_CCDC4
_database_code_depnum_ccdc_archive 'CCDC 1859407'
_audit_update_record             
;
2018-07-31 deposited with the CCDC.
2018-10-03 downloaded from the CCDC.
;
_chemical_name_systematic        
5-Benzyl-3-isopropyl-1-phenyl-2-thioxoimidazolidin-4-one
_chemical_name_common            3i
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H20 N2 O S'
_chemical_formula_iupac          ?
_chemical_formula_weight         324.43

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   12.4130(15)
_cell_length_b                   17.816(2)
_cell_length_c                   7.9085(10)
_cell_angle_alpha                90
_cell_angle_beta                 106.841(2)
_cell_angle_gamma                90
_cell_volume                     1674.0(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    912
_cell_measurement_theta_min      2.2863
_cell_measurement_theta_max      21.4646
_cell_measurement_temperature    173

_exptl_crystal_description       Plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.100
_exptl_crystal_density_diffrn    1.287
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             688

_exptl_absorpt_coefficient_mu    0.199
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'SADABS (Sheldrick 1996)'
_exptl_absorpt_correction_T_min  0.88
_exptl_absorpt_correction_T_max  0.98

_exptl_special_details           'SADABS (Sheldrick 1996)'

_diffrn_ambient_temperature      173

_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              ?

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'Bruker APEXII CCD area detector'
_diffrn_measurement_method       'Phi and Omega scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            9554
_diffrn_reflns_av_R_equivalents  0.0561
_diffrn_reflns_av_unetI/netI     0.0839
_diffrn_reflns_theta_min         1.71
_diffrn_reflns_theta_max         27.66
_diffrn_reflns_theta_full        27.66
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measured_fraction_theta_full 0.980
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       9

_refine_special_details          
;
;

_reflns_number_total             3838
_reflns_number_gt                2379
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0924
_refine_ls_R_factor_gt           0.0512
_refine_ls_wR_factor_gt          0.1170
_refine_ls_wR_factor_ref         0.1447
_refine_ls_goodness_of_fit_ref   0.929
_refine_ls_restrained_S_all      0.929
_refine_ls_number_reflns         3838
_refine_ls_number_parameters     210
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0697P)²] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.225
_refine_diff_density_min         -0.293
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'

_computing_data_collection       'APEX2 (Bruker AXS, 2006)'
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'XSHEL (Bruker AXS,2002)'
_computing_publication_material  'XCIF (Bruker AXS, 2001)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 -0.0972(2) 0.29187(15) 0.5692(4) 0.0368(6) Uani d . . . 1 . .
H H1A -0.0617 0.2489 0.5294 0.055 Uiso calc U . R 1 . .
H H1B -0.1754 0.2964 0.4955 0.055 Uiso calc U . R 1 . .
H H1C -0.0957 0.2844 0.6927 0.055 Uiso calc U . R 1 . .
C C2 -0.03325(19) 0.36312(13) 0.5538(3) 0.0285(6) Uani d . . . 1 . .
H H2 -0.0397 0.3705 0.4259 0.034 Uiso calc U . R 1 . .
C C3 -0.0818(2) 0.43260(15) 0.6166(4) 0.0450(7) Uani d . . . 1 . .
H H3A -0.0858 0.4244 0.7372 0.067 Uiso calc U . R 1 . .
H H3B -0.1575 0.4422 0.538 0.067 Uiso calc U . R 1 . .
H H3C -0.0334 0.4759 0.6151 0.067 Uiso calc U . R 1 . .
C C4 0.17208(19) 0.35261(12) 0.5660(3) 0.0239(5) Uani d . . . 1 . .
C C5 0.1287(2) 0.34262(13) 0.8279(3) 0.0275(6) Uani d . . . 1 . .
C C6 0.25515(19) 0.33471(13) 0.8700(3) 0.0273(5) Uani d . . . 1 . .
H H6 0.2775 0.2826 0.9135 0.033 Uiso calc U . R 1 . .
C C7 0.3193(2) 0.39135(13) 1.0095(3) 0.0294(6) Uani d . . . 1 . .
H H7A 0.3021 0.3811 1.122 0.035 Uiso calc U . R 1 . .
H H7B 0.4011 0.3837 1.0303 0.035 Uiso calc U . R 1 . .
C C8 0.29113(19) 0.47217(13) 0.9588(3) 0.0275(5) Uani d . . . 1 . .
C C9 0.1985(2) 0.50715(15) 0.9907(3) 0.0367(6) Uani d . . . 1 . .
H H9 0.1525 0.4797 1.046 0.044 Uiso calc U . R 1 . .
C C10 0.1727(2) 0.58093(15) 0.9432(4) 0.0401(7) Uani d . . . 1 . .
H H10 0.1084 0.6036 0.964 0.048 Uiso calc U . R 1 . .
C C11 0.2400(2) 0.62181(15) 0.8654(3) 0.0399(7) Uani d . . . 1 . .
H H11 0.2227 0.6728 0.8339 0.048 Uiso calc U . R 1 . .
C C12 0.3324(2) 0.58842(14) 0.8334(3) 0.0378(6) Uani d . . . 1 . .
H H12 0.379 0.6164 0.7801 0.045 Uiso calc U . R 1 . .
C C13 0.3572(2) 0.51418(14) 0.8789(3) 0.0322(6) Uani d . . . 1 . .
H H13 0.4206 0.4915 0.8552 0.039 Uiso calc U . R 1 . .
C C14 0.38121(19) 0.34143(13) 0.6711(3) 0.0271(5) Uani d . . . 1 . .
C C15 0.4125(2) 0.39336(14) 0.5636(3) 0.0345(6) Uani d . . . 1 . .
H H15 0.3596 0.4289 0.4981 0.041 Uiso calc U . R 1 . .
C C16 0.5220(2) 0.39279(16) 0.5529(4) 0.0463(8) Uani d . . . 1 . .
H H16 0.5438 0.4279 0.4786 0.056 Uiso calc U . R 1 . .
C C17 0.5995(2) 0.34213(18) 0.6484(4) 0.0502(8) Uani d . . . 1 . .
H H17 0.6746 0.3426 0.6412 0.06 Uiso calc U . R 1 . .
C C18 0.5673(2) 0.29053(17) 0.7549(4) 0.0457(7) Uani d . . . 1 . .
H H18 0.6207 0.2555 0.8213 0.055 Uiso calc U . R 1 . .
C C19 0.4584(2) 0.28950(14) 0.7656(3) 0.0345(6) Uani d . . . 1 . .
H H19 0.4365 0.2533 0.8374 0.041 Uiso calc U . R 1 . .
N N1 0.08723(15) 0.35427(10) 0.6486(2) 0.0249(4) Uani d . . . 1 . .
N N2 0.27145(15) 0.34395(10) 0.6949(2) 0.0240(4) Uani d . . . 1 . .
O O1 0.07381(14) 0.33990(10) 0.9321(2) 0.0357(4) Uani d . . . 1 . .
S S1 0.15065(5) 0.35760(3) 0.34985(8) 0.03093(19) Uani d . . . 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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C2 . 1.521(3) ?
C1 H1A . 0.98 ?
C1 H1B . 0.98 ?
C1 H1C . 0.98 ?
C2 N1 . 1.475(3) ?
C2 C3 . 1.522(3) ?
C2 H2 . 1.0 ?
C3 H3A . 0.98 ?
C3 H3B . 0.98 ?
C3 H3C . 0.98 ?
C4 N2 . 1.362(3) ?
C4 N1 . 1.391(3) ?
C4 S1 . 1.655(2) ?
C5 O1 . 1.213(3) ?
C5 N1 . 1.377(3) ?
C5 C6 . 1.513(3) ?
C6 N2 . 1.466(3) ?
C6 C7 . 1.536(3) ?
C6 H6 . 1.0 ?
C7 C8 . 1.508(3) ?
C7 H7A . 0.99 ?
C7 H7B . 0.99 ?
C8 C13 . 1.390(3) ?
C8 C9 . 1.393(3) ?
C9 C10 . 1.379(4) ?
C9 H9 . 0.95 ?
C10 C11 . 1.380(4) ?
C10 H10 . 0.95 ?
C11 C12 . 1.379(4) ?
C11 H11 . 0.95 ?
C12 C13 . 1.382(3) ?
C12 H12 . 0.95 ?
C13 H13 . 0.95 ?
C14 C19 . 1.385(3) ?
C14 C15 . 1.386(3) ?
C14 N2 . 1.429(3) ?
C15 C16 . 1.386(3) ?
C15 H15 . 0.95 ?
C16 C17 . 1.374(4) ?
C16 H16 . 0.95 ?
C17 C18 . 1.382(4) ?
C17 H17 . 0.95 ?
C18 C19 . 1.378(3) ?
C18 H18 . 0.95 ?
C19 H19 . 0.95 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 C1 H1A . . 109.5 ?
C2 C1 H1B . . 109.5 ?
H1A C1 H1B . . 109.5 ?
C2 C1 H1C . . 109.5 ?
H1A C1 H1C . . 109.5 ?
H1B C1 H1C . . 109.5 ?
N1 C2 C1 . . 110.23(19) ?
N1 C2 C3 . . 111.1(2) ?
C1 C2 C3 . . 112.8(2) ?
N1 C2 H2 . . 107.5 ?
C1 C2 H2 . . 107.5 ?
C3 C2 H2 . . 107.5 ?
C2 C3 H3A . . 109.5 ?
C2 C3 H3B . . 109.5 ?
H3A C3 H3B . . 109.5 ?
C2 C3 H3C . . 109.5 ?
H3A C3 H3C . . 109.5 ?
H3B C3 H3C . . 109.5 ?
N2 C4 N1 . . 107.19(19) ?
N2 C4 S1 . . 128.23(17) ?
N1 C4 S1 . . 124.55(18) ?
O1 C5 N1 . . 126.1(2) ?
O1 C5 C6 . . 126.7(2) ?
N1 C5 C6 . . 107.18(19) ?
N2 C6 C5 . . 101.53(18) ?
N2 C6 C7 . . 114.84(19) ?
C5 C6 C7 . . 112.66(19) ?
N2 C6 H6 . . 109.2 ?
C5 C6 H6 . . 109.2 ?
C7 C6 H6 . . 109.2 ?
C8 C7 C6 . . 113.84(19) ?
C8 C7 H7A . . 108.8 ?
C6 C7 H7A . . 108.8 ?
C8 C7 H7B . . 108.8 ?
C6 C7 H7B . . 108.8 ?
H7A C7 H7B . . 107.7 ?
C13 C8 C9 . . 117.9(2) ?
C13 C8 C7 . . 120.9(2) ?
C9 C8 C7 . . 121.2(2) ?
C10 C9 C8 . . 121.1(2) ?
C10 C9 H9 . . 119.5 ?
C8 C9 H9 . . 119.5 ?
C9 C10 C11 . . 120.1(2) ?
C9 C10 H10 . . 120.0 ?
C11 C10 H10 . . 120.0 ?
C12 C11 C10 . . 119.8(3) ?
C12 C11 H11 . . 120.1 ?
C10 C11 H11 . . 120.1 ?
C11 C12 C13 . . 120.0(2) ?
C11 C12 H12 . . 120.0 ?
C13 C12 H12 . . 120.0 ?
C12 C13 C8 . . 121.1(2) ?
C12 C13 H13 . . 119.4 ?
C8 C13 H13 . . 119.4 ?
C19 C14 C15 . . 120.2(2) ?
C19 C14 N2 . . 119.2(2) ?
C15 C14 N2 . . 120.5(2) ?
C14 C15 C16 . . 119.1(3) ?
C14 C15 H15 . . 120.4 ?
C16 C15 H15 . . 120.4 ?
C17 C16 C15 . . 120.9(3) ?
C17 C16 H16 . . 119.5 ?
C15 C16 H16 . . 119.5 ?
C16 C17 C18 . . 119.5(3) ?
C16 C17 H17 . . 120.3 ?
C18 C17 H17 . . 120.3 ?
C19 C18 C17 . . 120.5(3) ?
C19 C18 H18 . . 119.7 ?
C17 C18 H18 . . 119.7 ?
C18 C19 C14 . . 119.7(3) ?
C18 C19 H19 . . 120.1 ?
C14 C19 H19 . . 120.1 ?
C5 N1 C4 . . 111.85(19) ?
C5 N1 C2 . . 124.18(19) ?
C4 N1 C2 . . 123.88(19) ?
C4 N2 C14 . . 126.58(19) ?
C4 N2 C6 . . 112.13(18) ?
C14 N2 C6 . . 121.26(19) ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
O1 C5 C6 N2 . . . . -179.2(2) ?
N1 C5 C6 N2 . . . . 0.3(2) ?
O1 C5 C6 C7 . . . . -55.8(3) ?
N1 C5 C6 C7 . . . . 123.6(2) ?
N2 C6 C7 C8 . . . . 57.7(3) ?
C5 C6 C7 C8 . . . . -57.9(3) ?
C6 C7 C8 C13 . . . . -95.2(3) ?
C6 C7 C8 C9 . . . . 85.0(3) ?
C13 C8 C9 C10 . . . . 0.5(4) ?
C7 C8 C9 C10 . . . . -179.6(2) ?
C8 C9 C10 C11 . . . . -1.1(4) ?
C9 C10 C11 C12 . . . . 0.8(4) ?
C10 C11 C12 C13 . . . . 0.1(4) ?
C11 C12 C13 C8 . . . . -0.7(4) ?
C9 C8 C13 C12 . . . . 0.4(4) ?
C7 C8 C13 C12 . . . . -179.5(2) ?
C19 C14 C15 C16 . . . . -0.3(4) ?
N2 C14 C15 C16 . . . . 175.5(2) ?
C14 C15 C16 C17 . . . . -0.6(4) ?
C15 C16 C17 C18 . . . . 0.7(4) ?
C16 C17 C18 C19 . . . . 0.1(4) ?
C17 C18 C19 C14 . . . . -1.1(4) ?
C15 C14 C19 C18 . . . . 1.2(4) ?
N2 C14 C19 C18 . . . . -174.7(2) ?
O1 C5 N1 C4 . . . . -178.7(2) ?
C6 C5 N1 C4 . . . . 1.9(3) ?
O1 C5 N1 C2 . . . . -1.9(4) ?
C6 C5 N1 C2 . . . . 178.61(19) ?
N2 C4 N1 C5 . . . . -3.4(2) ?
S1 C4 N1 C5 . . . . 174.74(17) ?
N2 C4 N1 C2 . . . . 179.85(19) ?
S1 C4 N1 C2 . . . . -2.0(3) ?
C1 C2 N1 C5 . . . . -62.8(3) ?
C3 C2 N1 C5 . . . . 63.0(3) ?
C1 C2 N1 C4 . . . . 113.5(2) ?
C3 C2 N1 C4 . . . . -120.7(2) ?
N1 C4 N2 C14 . . . . -178.14(19) ?
S1 C4 N2 C14 . . . . 3.8(3) ?
N1 C4 N2 C6 . . . . 3.6(2) ?
S1 C4 N2 C6 . . . . -174.46(17) ?
C19 C14 N2 C4 . . . . -138.4(2) ?
C15 C14 N2 C4 . . . . 45.7(3) ?
C19 C14 N2 C6 . . . . 39.7(3) ?
C15 C14 N2 C6 . . . . -136.1(2) ?
C5 C6 N2 C4 . . . . -2.4(2) ?
C7 C6 N2 C4 . . . . -124.2(2) ?
C5 C6 N2 C14 . . . . 179.24(18) ?
C7 C6 N2 C14 . . . . 57.4(3) ?


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: CHCl3 and Hexane'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_I_CCDC5
_database_code_depnum_ccdc_archive 'CCDC 1859355'
_audit_update_record             
;
2018-07-31 deposited with the CCDC.
2018-10-03 downloaded from the CCDC.
;
_chemical_name_systematic        N',5-Dibenzyl-N-phenyl-2-thiohydantoin
_chemical_name_common            3j
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H20 N2 O S'
_chemical_formula_iupac          ?
_chemical_formula_weight         372.47

_chemical_melting_point          126-127

_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.887(2)
_cell_length_b                   9.348(2)
_cell_length_c                   12.182(3)
_cell_angle_alpha                80.025(3)
_cell_angle_beta                 72.125(3)
_cell_angle_gamma                88.273(3)
_cell_volume                     948.3(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2985
_cell_measurement_theta_min      2.2128
_cell_measurement_theta_max      27.5491
_cell_measurement_temperature    173

_exptl_crystal_description       block
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.300
_exptl_crystal_density_diffrn    1.304
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             392

_exptl_absorpt_coefficient_mu    0.186
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'SADABS (Sheldrick 1996)'
_exptl_absorpt_correction_T_min  0.88
_exptl_absorpt_correction_T_max  0.95

_exptl_special_details           'SADABS (Sheldrick 1996)'

_diffrn_ambient_temperature      173

_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              ?

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'Bruker APEXII CCD area detector'
_diffrn_measurement_method       'Phi and Omega scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            5472
_diffrn_reflns_av_R_equivalents  0.0157
_diffrn_reflns_av_unetI/netI     0.0264
_diffrn_reflns_theta_min         2.213
_diffrn_reflns_theta_max         27.589
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.940
_diffrn_measured_fraction_theta_full 0.979
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       15

_refine_special_details          
;
;

_reflns_number_total             4141
_reflns_number_gt                3585
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0429
_refine_ls_R_factor_gt           0.0365
_refine_ls_wR_factor_gt          0.0914
_refine_ls_wR_factor_ref         0.0954
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_restrained_S_all      1.065
_refine_ls_number_reflns         4141
_refine_ls_number_parameters     244
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0405P)²+0.3064P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     difmap
_atom_sites_solution_secondary   direct

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.343
_refine_diff_density_min         -0.290
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'

_computing_data_collection       'APEX2 (Bruker AXS, 2006)'
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'XSHEL (Bruker AXS,2002)'
_computing_publication_material  'XCIF (Bruker AXS, 2001)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.57248(15) 0.65879(14) 0.54813(11) 0.0247(3) Uani d . . . 1 . .
C C2 0.48738(16) 0.47734(15) 0.73685(12) 0.0306(3) Uani d . . . 1 . .
H H2A 0.5358 0.3866 0.7636 0.037 Uiso calc U . R 1 . .
H H2B 0.4004 0.45 0.7091 0.037 Uiso calc U . R 1 . .
C C3 0.41832(15) 0.55435(14) 0.84003(11) 0.0265(3) Uani d . . . 1 . .
C C4 0.26429(18) 0.51961(19) 0.91070(14) 0.0431(4) Uani d . . . 1 . .
H H4 0.2016 0.4549 0.8897 0.052 Uiso calc U . R 1 . .
C C5 0.20104(19) 0.5785(2) 1.01168(15) 0.0483(4) Uani d . . . 1 . .
H H5 0.0961 0.5525 1.0601 0.058 Uiso calc U . R 1 . .
C C6 0.28894(19) 0.67402(17) 1.04203(12) 0.0381(3) Uani d . . . 1 . .
H H6 0.2451 0.715 1.1108 0.046 Uiso calc U . R 1 . .
C C7 0.44146(19) 0.71006(16) 0.97195(12) 0.0361(3) Uani d . . . 1 . .
H H7 0.5028 0.7765 0.9925 0.043 Uiso calc U . R 1 . .
C C8 0.50637(17) 0.64997(15) 0.87143(12) 0.0306(3) Uani d . . . 1 . .
H H8 0.612 0.6749 0.8241 0.037 Uiso calc U . R 1 . .
C C9 0.76575(15) 0.54210(14) 0.61647(11) 0.0265(3) Uani d . . . 1 . .
C C10 0.84699(14) 0.64101(14) 0.50257(11) 0.0256(3) Uani d . . . 1 . .
H H10 0.905 0.5809 0.4431 0.031 Uiso calc U . R 1 . .
C C11 0.96288(16) 0.75150(16) 0.51479(12) 0.0326(3) Uani d . . . 1 . .
H H11A 1.059 0.7003 0.523 0.039 Uiso calc U . R 1 . .
H H11B 0.995 0.8245 0.442 0.039 Uiso calc U . R 1 . .
C C12 0.89693(16) 0.82938(16) 0.61732(12) 0.0325(3) Uani d . . . 1 . .
C C13 0.79179(18) 0.94254(16) 0.61403(14) 0.0372(3) Uani d . . . 1 . .
H H13 0.7616 0.9725 0.5453 0.045 Uiso calc U . R 1 . .
C C14 0.7307(2) 1.01185(18) 0.70927(16) 0.0467(4) Uani d . . . 1 . .
H H14 0.6595 1.089 0.7055 0.056 Uiso calc U . R 1 . .
C C15 0.7730(2) 0.9691(2) 0.80959(16) 0.0539(5) Uani d . . . 1 . .
H H15 0.7301 1.0159 0.8754 0.065 Uiso calc U . R 1 . .
C C16 0.8778(2) 0.8583(2) 0.81411(16) 0.0575(5) Uani d . . . 1 . .
H H16 0.9074 0.8292 0.8831 0.069 Uiso calc U . R 1 . .
C C17 0.9404(2) 0.7886(2) 0.71866(15) 0.0460(4) Uani d . . . 1 . .
H H17 1.0133 0.7129 0.7225 0.055 Uiso calc U . R 1 . .
C C18 0.73736(15) 0.79907(14) 0.35779(11) 0.0257(3) Uani d . . . 1 . .
C C19 0.65798(18) 0.92799(16) 0.34689(13) 0.0367(3) Uani d . . . 1 . .
H H19 0.5849 0.9569 0.4139 0.044 Uiso calc U . R 1 . .
C C20 0.6857(2) 1.01470(18) 0.23771(15) 0.0444(4) Uani d . . . 1 . .
H H20 0.6312 1.1031 0.23 0.053 Uiso calc U . R 1 . .
C C21 0.79258(19) 0.97281(18) 0.13980(13) 0.0411(4) Uani d . . . 1 . .
H H21 0.8093 1.031 0.0648 0.049 Uiso calc U . R 1 . .
C C22 0.87448(18) 0.84636(17) 0.15179(13) 0.0375(3) Uani d . . . 1 . .
H H22 0.9496 0.8189 0.085 0.045 Uiso calc U . R 1 . .
C C23 0.84832(16) 0.75892(15) 0.26037(12) 0.0309(3) Uani d . . . 1 . .
H H23 0.9057 0.6723 0.2682 0.037 Uiso calc U . R 1 . .
N N1 0.71274(12) 0.70845(12) 0.46934(9) 0.0244(2) Uani d . . . 1 . .
N N2 0.60640(12) 0.56309(12) 0.63850(9) 0.0251(2) Uani d . . . 1 . .
O O1 0.82824(12) 0.46001(12) 0.67693(8) 0.0370(2) Uani d . . . 1 . .
S S1 0.39157(4) 0.69644(4) 0.54318(3) 0.03514(11) Uani d . . . 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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 N1 . 1.3552(16) ?
C1 N2 . 1.3962(17) ?
C1 S1 . 1.6525(14) ?
C2 N2 . 1.4619(16) ?
C2 C3 . 1.5126(18) ?
C2 H2A . 0.99 ?
C2 H2B . 0.99 ?
C3 C8 . 1.379(2) ?
C3 C4 . 1.3881(19) ?
C4 C5 . 1.387(2) ?
C4 H4 . 0.95 ?
C5 C6 . 1.370(2) ?
C5 H5 . 0.95 ?
C6 C7 . 1.377(2) ?
C6 H6 . 0.95 ?
C7 C8 . 1.390(2) ?
C7 H7 . 0.95 ?
C8 H8 . 0.95 ?
C9 O1 . 1.2121(17) ?
C9 N2 . 1.3726(17) ?
C9 C10 . 1.5107(18) ?
C10 N1 . 1.4654(16) ?
C10 C11 . 1.5366(19) ?
C10 H10 . 1.0 ?
C11 C12 . 1.508(2) ?
C11 H11A . 0.99 ?
C11 H11B . 0.99 ?
C12 C17 . 1.393(2) ?
C12 C13 . 1.394(2) ?
C13 C14 . 1.383(2) ?
C13 H13 . 0.95 ?
C14 C15 . 1.378(3) ?
C14 H14 . 0.95 ?
C15 C16 . 1.377(3) ?
C15 H15 . 0.95 ?
C16 C17 . 1.389(3) ?
C16 H16 . 0.95 ?
C17 H17 . 0.95 ?
C18 C19 . 1.3851(19) ?
C18 C23 . 1.3911(18) ?
C18 N1 . 1.4290(16) ?
C19 C20 . 1.387(2) ?
C19 H19 . 0.95 ?
C20 C21 . 1.386(2) ?
C20 H20 . 0.95 ?
C21 C22 . 1.379(2) ?
C21 H21 . 0.95 ?
C22 C23 . 1.385(2) ?
C22 H22 . 0.95 ?
C23 H23 . 0.95 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N1 C1 N2 . . 107.08(11) ?
N1 C1 S1 . . 128.85(10) ?
N2 C1 S1 . . 124.05(9) ?
N2 C2 C3 . . 114.33(11) ?
N2 C2 H2A . . 108.7 ?
C3 C2 H2A . . 108.7 ?
N2 C2 H2B . . 108.7 ?
C3 C2 H2B . . 108.7 ?
H2A C2 H2B . . 107.6 ?
C8 C3 C4 . . 118.69(13) ?
C8 C3 C2 . . 122.36(12) ?
C4 C3 C2 . . 118.78(12) ?
C5 C4 C3 . . 120.60(15) ?
C5 C4 H4 . . 119.7 ?
C3 C4 H4 . . 119.7 ?
C6 C5 C4 . . 120.40(14) ?
C6 C5 H5 . . 119.8 ?
C4 C5 H5 . . 119.8 ?
C5 C6 C7 . . 119.42(14) ?
C5 C6 H6 . . 120.3 ?
C7 C6 H6 . . 120.3 ?
C6 C7 C8 . . 120.50(14) ?
C6 C7 H7 . . 119.7 ?
C8 C7 H7 . . 119.7 ?
C3 C8 C7 . . 120.39(13) ?
C3 C8 H8 . . 119.8 ?
C7 C8 H8 . . 119.8 ?
O1 C9 N2 . . 126.45(12) ?
O1 C9 C10 . . 127.02(12) ?
N2 C9 C10 . . 106.53(11) ?
N1 C10 C9 . . 102.14(10) ?
N1 C10 C11 . . 113.40(11) ?
C9 C10 C11 . . 113.16(11) ?
N1 C10 H10 . . 109.3 ?
C9 C10 H10 . . 109.3 ?
C11 C10 H10 . . 109.3 ?
C12 C11 C10 . . 114.18(11) ?
C12 C11 H11A . . 108.7 ?
C10 C11 H11A . . 108.7 ?
C12 C11 H11B . . 108.7 ?
C10 C11 H11B . . 108.7 ?
H11A C11 H11B . . 107.6 ?
C17 C12 C13 . . 118.31(15) ?
C17 C12 C11 . . 120.08(14) ?
C13 C12 C11 . . 121.61(13) ?
C14 C13 C12 . . 120.99(16) ?
C14 C13 H13 . . 119.5 ?
C12 C13 H13 . . 119.5 ?
C15 C14 C13 . . 120.11(17) ?
C15 C14 H14 . . 119.9 ?
C13 C14 H14 . . 119.9 ?
C16 C15 C14 . . 119.71(16) ?
C16 C15 H15 . . 120.1 ?
C14 C15 H15 . . 120.1 ?
C15 C16 C17 . . 120.57(17) ?
C15 C16 H16 . . 119.7 ?
C17 C16 H16 . . 119.7 ?
C16 C17 C12 . . 120.29(18) ?
C16 C17 H17 . . 119.9 ?
C12 C17 H17 . . 119.9 ?
C19 C18 C23 . . 120.19(13) ?
C19 C18 N1 . . 120.99(12) ?
C23 C18 N1 . . 118.76(12) ?
C18 C19 C20 . . 119.75(14) ?
C18 C19 H19 . . 120.1 ?
C20 C19 H19 . . 120.1 ?
C21 C20 C19 . . 120.21(15) ?
C21 C20 H20 . . 119.9 ?
C19 C20 H20 . . 119.9 ?
C22 C21 C20 . . 119.73(14) ?
C22 C21 H21 . . 120.1 ?
C20 C21 H21 . . 120.1 ?
C21 C22 C23 . . 120.65(14) ?
C21 C22 H22 . . 119.7 ?
C23 C22 H22 . . 119.7 ?
C22 C23 C18 . . 119.42(13) ?
C22 C23 H23 . . 120.3 ?
C18 C23 H23 . . 120.3 ?
C1 N1 C18 . . 127.19(11) ?
C1 N1 C10 . . 111.87(10) ?
C18 N1 C10 . . 120.39(10) ?
C9 N2 C1 . . 112.23(10) ?
C9 N2 C2 . . 122.75(11) ?
C1 N2 C2 . . 124.40(11) ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
N2 C2 C3 C8 . . . . -34.29(19) ?
N2 C2 C3 C4 . . . . 150.51(14) ?
C8 C3 C4 C5 . . . . -0.8(2) ?
C2 C3 C4 C5 . . . . 174.54(15) ?
C3 C4 C5 C6 . . . . 1.2(3) ?
C4 C5 C6 C7 . . . . -0.6(3) ?
C5 C6 C7 C8 . . . . -0.2(2) ?
C4 C3 C8 C7 . . . . 0.0(2) ?
C2 C3 C8 C7 . . . . -175.22(13) ?
C6 C7 C8 C3 . . . . 0.5(2) ?
O1 C9 C10 N1 . . . . 178.23(13) ?
N2 C9 C10 N1 . . . . -1.73(13) ?
O1 C9 C10 C11 . . . . -59.50(18) ?
N2 C9 C10 C11 . . . . 120.54(12) ?
N1 C10 C11 C12 . . . . 68.58(15) ?
C9 C10 C11 C12 . . . . -47.16(16) ?
C10 C11 C12 C17 . . . . 102.59(16) ?
C10 C11 C12 C13 . . . . -77.26(17) ?
C17 C12 C13 C14 . . . . -0.7(2) ?
C11 C12 C13 C14 . . . . 179.20(13) ?
C12 C13 C14 C15 . . . . -0.2(2) ?
C13 C14 C15 C16 . . . . 0.7(3) ?
C14 C15 C16 C17 . . . . -0.4(3) ?
C15 C16 C17 C12 . . . . -0.5(3) ?
C13 C12 C17 C16 . . . . 1.0(2) ?
C11 C12 C17 C16 . . . . -178.83(14) ?
C23 C18 C19 C20 . . . . 2.1(2) ?
N1 C18 C19 C20 . . . . 179.20(14) ?
C18 C19 C20 C21 . . . . -0.1(2) ?
C19 C20 C21 C22 . . . . -1.7(3) ?
C20 C21 C22 C23 . . . . 1.5(2) ?
C21 C22 C23 C18 . . . . 0.5(2) ?
C19 C18 C23 C22 . . . . -2.3(2) ?
N1 C18 C23 C22 . . . . -179.44(12) ?
N2 C1 N1 C18 . . . . 174.20(11) ?
S1 C1 N1 C18 . . . . -4.65(19) ?
N2 C1 N1 C10 . . . . 2.72(14) ?
S1 C1 N1 C10 . . . . -176.12(10) ?
C19 C18 N1 C1 . . . . 51.65(19) ?
C23 C18 N1 C1 . . . . -131.24(14) ?
C19 C18 N1 C10 . . . . -137.52(13) ?
C23 C18 N1 C10 . . . . 39.59(17) ?
C9 C10 N1 C1 . . . . -0.64(13) ?
C11 C10 N1 C1 . . . . -122.74(12) ?
C9 C10 N1 C18 . . . . -172.77(10) ?
C11 C10 N1 C18 . . . . 65.12(15) ?
O1 C9 N2 C1 . . . . -176.41(13) ?
C10 C9 N2 C1 . . . . 3.55(14) ?
O1 C9 N2 C2 . . . . -5.1(2) ?
C10 C9 N2 C2 . . . . 174.90(11) ?
N1 C1 N2 C9 . . . . -3.99(14) ?
S1 C1 N2 C9 . . . . 174.93(9) ?
N1 C1 N2 C2 . . . . -175.17(11) ?
S1 C1 N2 C2 . . . . 3.74(17) ?
C3 C2 N2 C9 . . . . 101.96(14) ?
C3 C2 N2 C1 . . . . -87.75(15) ?


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: CHCl3 and Hexane'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_I_CCDC6
_database_code_depnum_ccdc_archive 'CCDC 1859354'
_audit_update_record             
;
2018-07-31 deposited with the CCDC.
2018-10-03 downloaded from the CCDC.
;
_chemical_name_systematic        
N-Phenyl-N'-benzyl-6-phenyl-2-iminotetrahydro-1,3-thiazin-4-one
_chemical_name_common            2j
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H20 N2 O S'
_chemical_formula_iupac          ?
_chemical_formula_weight         372.47

_chemical_melting_point          201-202

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   13.613(2)
_cell_length_b                   5.3251(9)
_cell_length_c                   26.026(4)
_cell_angle_alpha                90
_cell_angle_beta                 95.958(3)
_cell_angle_gamma                90
_cell_volume                     1876.4(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1019
_cell_measurement_theta_min      2.2870
_cell_measurement_theta_max      23.3141
_cell_measurement_temperature    173.(2)

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.100
_exptl_crystal_density_diffrn    1.318
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             784

_exptl_absorpt_coefficient_mu    0.188
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'SADABS (Sheldrick 1996)'
_exptl_absorpt_correction_T_min  0.86
_exptl_absorpt_correction_T_max  0.98

_exptl_special_details           'SADABS (Sheldrick 1996)'

_diffrn_ambient_temperature      173.(2)

_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              ?

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'Bruker APEXII CCD area detector'
_diffrn_measurement_method       'Phi and Omega scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            10165
_diffrn_reflns_av_R_equivalents  0.0530
_diffrn_reflns_av_unetI/netI     0.0848
_diffrn_reflns_theta_min         1.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.989
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_limit_l_max       25

_refine_special_details          
;
;

_reflns_number_total             4244
_reflns_number_gt                2649
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0974
_refine_ls_R_factor_gt           0.0521
_refine_ls_wR_factor_gt          0.1235
_refine_ls_wR_factor_ref         0.1597
_refine_ls_goodness_of_fit_ref   0.966
_refine_ls_restrained_S_all      0.966
_refine_ls_number_reflns         4244
_refine_ls_number_parameters     244
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0763P)²] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap

_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.304
_refine_diff_density_min         -0.316
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'

_computing_data_collection       'APEX2 (Bruker AXS, 2006)'
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'XSHEL (Bruker AXS,2002)'
_computing_publication_material  'XCIF (Bruker AXS, 2001)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.42830(18) 0.4919(5) 0.37746(9) 0.0247(6) Uani d . . . 1 . .
C C2 0.45857(19) 0.8054(5) 0.30878(9) 0.0268(6) Uani d . . . 1 . .
C C3 0.56687(18) 0.8209(5) 0.32729(10) 0.0292(6) Uani d . . . 1 . .
H H3A 0.5761 0.94 0.3566 0.035 Uiso calc U . R 1 . .
H H3B 0.6026 0.8889 0.2991 0.035 Uiso calc U . R 1 . .
C C4 0.61195(18) 0.5719(5) 0.34427(10) 0.0279(6) Uani d . . . 1 . .
H H4 0.5964 0.4478 0.3157 0.034 Uiso calc U . R 1 . .
C C5 0.38425(19) 0.2332(6) 0.44453(10) 0.0335(7) Uani d . . . 1 . .
H H5A 0.4101 0.3405 0.4739 0.04 Uiso calc U . R 1 . .
H H5B 0.4366 0.1123 0.4377 0.04 Uiso calc U . R 1 . .
C C6 0.29442(19) 0.0911(5) 0.45860(9) 0.0280(6) Uani d . . . 1 . .
C C7 0.19943(19) 0.1649(5) 0.44054(10) 0.0326(7) Uani d . . . 1 . .
H H7 0.1899 0.3087 0.419 0.039 Uiso calc U . R 1 . .
C C8 0.1185(2) 0.0316(6) 0.45349(11) 0.0388(7) Uani d . . . 1 . .
H H8 0.0538 0.0841 0.4409 0.047 Uiso calc U . R 1 . .
C C9 0.1316(2) -0.1773(6) 0.48463(11) 0.0433(8) Uani d . . . 1 . .
H H9 0.076 -0.2698 0.4934 0.052 Uiso calc U . R 1 . .
C C10 0.2255(2) -0.2516(6) 0.50307(11) 0.0438(8) Uani d . . . 1 . .
H H10 0.2348 -0.3943 0.5249 0.053 Uiso calc U . R 1 . .
C C11 0.3067(2) -0.1180(5) 0.48974(10) 0.0359(7) Uani d . . . 1 . .
H H11 0.3714 -0.1714 0.5022 0.043 Uiso calc U . R 1 . .
C C12 0.29607(18) 0.6221(5) 0.31273(9) 0.0250(6) Uani d . . . 1 . .
C C13 0.23174(19) 0.8032(5) 0.32712(10) 0.0313(6) Uani d . . . 1 . .
H H13 0.2551 0.9387 0.3488 0.038 Uiso calc U . R 1 . .
C C14 0.1322(2) 0.7840(6) 0.30934(11) 0.0369(7) Uani d . . . 1 . .
H H14 0.0867 0.9052 0.3194 0.044 Uiso calc U . R 1 . .
C C15 0.0992(2) 0.5899(5) 0.27717(11) 0.0361(7) Uani d . . . 1 . .
H H15 0.0311 0.5782 0.265 0.043 Uiso calc U . R 1 . .
C C16 0.1648(2) 0.4115(5) 0.26253(10) 0.0339(7) Uani d . . . 1 . .
H H16 0.142 0.2791 0.2399 0.041 Uiso calc U . R 1 . .
C C17 0.26396(19) 0.4260(5) 0.28087(10) 0.0279(6) Uani d . . . 1 . .
H H17 0.3091 0.3023 0.2716 0.034 Uiso calc U . R 1 . .
C C18 0.72261(19) 0.5749(5) 0.35823(10) 0.0270(6) Uani d . . . 1 . .
C C19 0.7797(2) 0.3967(5) 0.33745(11) 0.0356(7) Uani d . . . 1 . .
H H19 0.7495 0.2757 0.3141 0.043 Uiso calc U . R 1 . .
C C20 0.8809(2) 0.3918(6) 0.35025(11) 0.0407(7) Uani d . . . 1 . .
H H20 0.9196 0.2668 0.3358 0.049 Uiso calc U . R 1 . .
C C21 0.9257(2) 0.5661(6) 0.38358(11) 0.0391(7) Uani d . . . 1 . .
H H21 0.9953 0.5634 0.3919 0.047 Uiso calc U . R 1 . .
C C22 0.8694(2) 0.7453(6) 0.40502(11) 0.0401(7) Uani d . . . 1 . .
H H22 0.9003 0.8652 0.4284 0.048 Uiso calc U . R 1 . .
C C23 0.7678(2) 0.7516(6) 0.39256(10) 0.0349(7) Uani d . . . 1 . .
H H23 0.7292 0.8757 0.4073 0.042 Uiso calc U . R 1 . .
N N1 0.36001(15) 0.3888(4) 0.39915(8) 0.0310(5) Uani d . . . 1 . .
N N2 0.40043(15) 0.6368(4) 0.33258(7) 0.0258(5) Uani d . . . 1 . .
O O1 0.42192(14) 0.9387(4) 0.27378(7) 0.0364(5) Uani d . . . 1 . .
S S1 0.55411(5) 0.46536(14) 0.40054(2) 0.0294(2) Uani d . . . 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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 N1 . 1.262(3) ?
C1 N2 . 1.418(3) ?
C1 S1 . 1.761(3) ?
C2 O1 . 1.220(3) ?
C2 N2 . 1.385(3) ?
C2 C3 . 1.505(3) ?
C3 C4 . 1.508(3) ?
C3 H3A . 0.99 ?
C3 H3B . 0.99 ?
C4 C18 . 1.513(3) ?
C4 S1 . 1.824(3) ?
C4 H4 . 1.0 ?
C5 N1 . 1.452(3) ?
C5 C6 . 1.515(3) ?
C5 H5A . 0.99 ?
C5 H5B . 0.99 ?
C6 C11 . 1.377(4) ?
C6 C7 . 1.386(4) ?
C7 C8 . 1.381(4) ?
C7 H7 . 0.95 ?
C8 C9 . 1.377(4) ?
C8 H8 . 0.95 ?
C9 C10 . 1.376(4) ?
C9 H9 . 0.95 ?
C10 C11 . 1.388(4) ?
C10 H10 . 0.95 ?
C11 H11 . 0.95 ?
C12 C17 . 1.376(3) ?
C12 C13 . 1.380(3) ?
C12 N2 . 1.463(3) ?
C13 C14 . 1.390(4) ?
C13 H13 . 0.95 ?
C14 C15 . 1.376(4) ?
C14 H14 . 0.95 ?
C15 C16 . 1.385(4) ?
C15 H15 . 0.95 ?
C16 C17 . 1.386(3) ?
C16 H16 . 0.95 ?
C17 H17 . 0.95 ?
C18 C19 . 1.373(4) ?
C18 C23 . 1.396(4) ?
C19 C20 . 1.384(4) ?
C19 H19 . 0.95 ?
C20 C21 . 1.369(4) ?
C20 H20 . 0.95 ?
C21 C22 . 1.378(4) ?
C21 H21 . 0.95 ?
C22 C23 . 1.388(4) ?
C22 H22 . 0.95 ?
C23 H23 . 0.95 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N1 C1 N2 . . 117.3(2) ?
N1 C1 S1 . . 123.2(2) ?
N2 C1 S1 . . 119.49(18) ?
O1 C2 N2 . . 120.2(2) ?
O1 C2 C3 . . 121.2(2) ?
N2 C2 C3 . . 118.6(2) ?
C2 C3 C4 . . 113.6(2) ?
C2 C3 H3A . . 108.8 ?
C4 C3 H3A . . 108.8 ?
C2 C3 H3B . . 108.8 ?
C4 C3 H3B . . 108.8 ?
H3A C3 H3B . . 107.7 ?
C3 C4 C18 . . 115.2(2) ?
C3 C4 S1 . . 108.21(18) ?
C18 C4 S1 . . 108.22(16) ?
C3 C4 H4 . . 108.3 ?
C18 C4 H4 . . 108.3 ?
S1 C4 H4 . . 108.3 ?
N1 C5 C6 . . 111.1(2) ?
N1 C5 H5A . . 109.4 ?
C6 C5 H5A . . 109.4 ?
N1 C5 H5B . . 109.4 ?
C6 C5 H5B . . 109.4 ?
H5A C5 H5B . . 108.0 ?
C11 C6 C7 . . 118.7(2) ?
C11 C6 C5 . . 119.6(2) ?
C7 C6 C5 . . 121.6(2) ?
C8 C7 C6 . . 120.7(3) ?
C8 C7 H7 . . 119.6 ?
C6 C7 H7 . . 119.6 ?
C9 C8 C7 . . 120.1(3) ?
C9 C8 H8 . . 120.0 ?
C7 C8 H8 . . 120.0 ?
C10 C9 C8 . . 119.8(3) ?
C10 C9 H9 . . 120.1 ?
C8 C9 H9 . . 120.1 ?
C9 C10 C11 . . 120.0(3) ?
C9 C10 H10 . . 120.0 ?
C11 C10 H10 . . 120.0 ?
C6 C11 C10 . . 120.7(3) ?
C6 C11 H11 . . 119.7 ?
C10 C11 H11 . . 119.7 ?
C17 C12 C13 . . 121.5(2) ?
C17 C12 N2 . . 119.3(2) ?
C13 C12 N2 . . 119.1(2) ?
C12 C13 C14 . . 118.8(3) ?
C12 C13 H13 . . 120.6 ?
C14 C13 H13 . . 120.6 ?
C15 C14 C13 . . 120.2(3) ?
C15 C14 H14 . . 119.9 ?
C13 C14 H14 . . 119.9 ?
C14 C15 C16 . . 120.2(3) ?
C14 C15 H15 . . 119.9 ?
C16 C15 H15 . . 119.9 ?
C15 C16 C17 . . 120.0(3) ?
C15 C16 H16 . . 120.0 ?
C17 C16 H16 . . 120.0 ?
C12 C17 C16 . . 119.1(2) ?
C12 C17 H17 . . 120.4 ?
C16 C17 H17 . . 120.4 ?
C19 C18 C23 . . 119.2(2) ?
C19 C18 C4 . . 119.2(2) ?
C23 C18 C4 . . 121.5(2) ?
C18 C19 C20 . . 120.6(3) ?
C18 C19 H19 . . 119.7 ?
C20 C19 H19 . . 119.7 ?
C21 C20 C19 . . 120.4(3) ?
C21 C20 H20 . . 119.8 ?
C19 C20 H20 . . 119.8 ?
C20 C21 C22 . . 119.8(3) ?
C20 C21 H21 . . 120.1 ?
C22 C21 H21 . . 120.1 ?
C21 C22 C23 . . 120.3(3) ?
C21 C22 H22 . . 119.8 ?
C23 C22 H22 . . 119.8 ?
C22 C23 C18 . . 119.7(3) ?
C22 C23 H23 . . 120.1 ?
C18 C23 H23 . . 120.1 ?
C1 N1 C5 . . 119.7(2) ?
C2 N2 C1 . . 127.2(2) ?
C2 N2 C12 . . 117.1(2) ?
C1 N2 C12 . . 115.39(19) ?
C1 S1 C4 . . 100.76(11) ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
O1 C2 C3 C4 . . . . -145.4(2) ?
N2 C2 C3 C4 . . . . 35.0(3) ?
C2 C3 C4 C18 . . . . 174.3(2) ?
C2 C3 C4 S1 . . . . -64.4(2) ?
N1 C5 C6 C11 . . . . 160.7(2) ?
N1 C5 C6 C7 . . . . -18.8(4) ?
C11 C6 C7 C8 . . . . 0.0(4) ?
C5 C6 C7 C8 . . . . 179.5(2) ?
C6 C7 C8 C9 . . . . -0.1(4) ?
C7 C8 C9 C10 . . . . 0.5(4) ?
C8 C9 C10 C11 . . . . -0.8(5) ?
C7 C6 C11 C10 . . . . -0.4(4) ?
C5 C6 C11 C10 . . . . -179.9(3) ?
C9 C10 C11 C6 . . . . 0.8(4) ?
C17 C12 C13 C14 . . . . 0.8(4) ?
N2 C12 C13 C14 . . . . -178.1(2) ?
C12 C13 C14 C15 . . . . -1.2(4) ?
C13 C14 C15 C16 . . . . 0.4(4) ?
C14 C15 C16 C17 . . . . 0.9(4) ?
C13 C12 C17 C16 . . . . 0.5(4) ?
N2 C12 C17 C16 . . . . 179.4(2) ?
C15 C16 C17 C12 . . . . -1.4(4) ?
C3 C4 C18 C19 . . . . -130.6(3) ?
S1 C4 C18 C19 . . . . 108.1(2) ?
C3 C4 C18 C23 . . . . 50.7(3) ?
S1 C4 C18 C23 . . . . -70.6(3) ?
C23 C18 C19 C20 . . . . -0.1(4) ?
C4 C18 C19 C20 . . . . -178.8(2) ?
C18 C19 C20 C21 . . . . -0.5(4) ?
C19 C20 C21 C22 . . . . 0.8(4) ?
C20 C21 C22 C23 . . . . -0.7(4) ?
C21 C22 C23 C18 . . . . 0.1(4) ?
C19 C18 C23 C22 . . . . 0.2(4) ?
C4 C18 C23 C22 . . . . 178.9(2) ?
N2 C1 N1 C5 . . . . 178.5(2) ?
S1 C1 N1 C5 . . . . -2.0(4) ?
C6 C5 N1 C1 . . . . -169.8(2) ?
O1 C2 N2 C1 . . . . -171.6(2) ?
C3 C2 N2 C1 . . . . 7.9(4) ?
O1 C2 N2 C12 . . . . 2.0(3) ?
C3 C2 N2 C12 . . . . -178.5(2) ?
N1 C1 N2 C2 . . . . 165.9(2) ?
S1 C1 N2 C2 . . . . -13.7(3) ?
N1 C1 N2 C12 . . . . -7.8(3) ?
S1 C1 N2 C12 . . . . 172.64(18) ?
C17 C12 N2 C2 . . . . 101.9(3) ?
C13 C12 N2 C2 . . . . -79.2(3) ?
C17 C12 N2 C1 . . . . -83.8(3) ?
C13 C12 N2 C1 . . . . 95.2(3) ?
N1 C1 S1 C4 . . . . 164.4(2) ?
N2 C1 S1 C4 . . . . -16.1(2) ?
C3 C4 S1 C1 . . . . 51.5(2) ?
C18 C4 S1 C1 . . . . 176.98(18) ?


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: CHCl3 and Hexane'
