# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_EPR-form-III
_database_code_depnum_ccdc_archive 'CCDC 1448699'
_audit_update_record             
;
2016-01-20 deposited with the CCDC.
2016-02-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
; 
 5-[(1Z, 2E)-2-methyl-3-phenylpropenylidene]-4-oxo2-thioxo-3-thiazolidineacetic acid  
;
_chemical_name_common            Epalrestat
_chemical_melting_point          495.39
_chemical_formula_moiety         'C15 H13 N O3 S2'
_chemical_formula_sum            'C15 H13 N O3 S2'
_chemical_formula_weight         319.38

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   14.7831(13)
_cell_length_b                   5.6288(5)
_cell_length_c                   18.2621(16)
_cell_angle_alpha                90
_cell_angle_beta                 98.364(8)
_cell_angle_gamma                90
_cell_volume                     1503.4(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    1710
_cell_measurement_theta_min      3.8780
_cell_measurement_theta_max      27.4090

_exptl_crystal_description       Needle
_exptl_crystal_colour            Yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.411
_exptl_crystal_F_000             664
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_exptl_absorpt_coefficient_mu    0.362
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.82239
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.30a (release 13-01-2014 CrysAlis171 .NET)
(compiled Jan 13 2014,18:40:09)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6015
_diffrn_reflns_av_unetI/netI     0.0378
_diffrn_reflns_av_R_equivalents  0.0263
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.785
_diffrn_reflns_theta_max         25.027
_diffrn_reflns_theta_full        25.027
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2654
_reflns_number_gt                1989
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.30a (release 13-01-2014 CrysAlis171 .NET)
(compiled Jan 13 2014,18:40:09)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.30a (release 13-01-2014 CrysAlis171 .NET)
(compiled Jan 13 2014,18:40:09)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.30a (release 13-01-2014 CrysAlis171 .NET)
(compiled Jan 13 2014,18:40:09)
;
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0392P)²+0.4291P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2654
_refine_ls_number_parameters     195
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0619
_refine_ls_R_factor_gt           0.0427
_refine_ls_wR_factor_ref         0.0996
_refine_ls_wR_factor_gt          0.0907
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_restrained_S_all      1.026
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.90427(4) 1.30901(12) 0.05578(3) 0.0481(2) Uani 1 1 d . . . . .
S2 S 0.81413(5) 1.71462(14) -0.02860(4) 0.0665(2) Uani 1 1 d . . . . .
N1 N 0.77209(12) 1.5387(3) 0.09812(10) 0.0417(5) Uani 1 1 d . . . . .
O3 O 0.55102(14) 1.7780(4) 0.03834(13) 0.0737(7) Uani 1 1 d . . . . .
C11 C 0.86636(14) 1.2137(4) 0.13747(13) 0.0403(6) Uani 1 1 d . . . . .
O1 O 0.74461(13) 1.3413(3) 0.20177(10) 0.0683(6) Uani 1 1 d . . . . .
C12 C 0.82401(15) 1.5346(4) 0.04175(13) 0.0438(6) Uani 1 1 d . . . . .
C14 C 0.69745(15) 1.7041(4) 0.09902(14) 0.0497(6) Uani 1 1 d . . . . .
H14A H 0.7133 1.8550 0.0786 0.060 Uiso 1 1 calc R U . . .
H14B H 0.6876 1.7307 0.1497 0.060 Uiso 1 1 calc R U . . .
C2 C 1.10239(17) 0.4234(4) 0.22234(15) 0.0536(7) Uani 1 1 d . . . . .
H2 H 1.0888 0.4459 0.1715 0.064 Uiso 1 1 calc R U . . .
C7 C 0.98592(16) 0.7318(4) 0.24568(14) 0.0512(6) Uani 1 1 d . . . . .
H7 H 0.9429 0.7481 0.2778 0.061 Uiso 1 1 calc R U . . .
C13 C 0.78919(15) 1.3621(4) 0.15173(13) 0.0448(6) Uani 1 1 d . . . . .
C1 C 1.05648(16) 0.5554(4) 0.26949(14) 0.0496(6) Uani 1 1 d . . . . .
C8 C 0.97119(15) 0.8754(4) 0.18624(13) 0.0419(6) Uani 1 1 d . . . . .
C15 C 0.61125(16) 1.6119(5) 0.05499(15) 0.0519(7) Uani 1 1 d . . . . .
C6 C 1.0787(2) 0.5136(6) 0.34434(16) 0.0797(10) Uani 1 1 d . . . . .
H6 H 1.0481 0.5971 0.3772 0.096 Uiso 1 1 calc R U . . .
C5 C 1.1449(2) 0.3519(7) 0.37183(18) 0.0871(11) Uani 1 1 d . . . . .
H5 H 1.1600 0.3307 0.4226 0.104 Uiso 1 1 calc R U . . .
O2 O 0.60075(12) 1.4045(3) 0.03811(12) 0.0700(6) Uani 1 1 d . . . . .
C3 C 1.16745(18) 0.2603(5) 0.24966(17) 0.0625(7) Uani 1 1 d . . . . .
H3 H 1.1977 0.1742 0.2171 0.075 Uiso 1 1 calc R U . . .
C9 C 1.03035(16) 0.8811(4) 0.12604(14) 0.0493(6) Uani 1 1 d . . . . .
H9B H 1.0885 0.8099 0.1437 0.074 Uiso 1 1 calc R U . . .
H9A H 1.0393 1.0428 0.1120 0.074 Uiso 1 1 calc R U . . .
H9C H 1.0011 0.7942 0.0839 0.074 Uiso 1 1 calc R U . . .
C4 C 1.1883(2) 0.2226(6) 0.32393(19) 0.0721(9) Uani 1 1 d . . . . .
H4 H 1.2318 0.1096 0.3419 0.086 Uiso 1 1 calc R U . . .
C10 C 0.89644(15) 1.0389(4) 0.18419(13) 0.0435(6) Uani 1 1 d . . . . .
H10 H 0.8624 1.0195 0.2228 0.052 Uiso 1 1 calc R U . . .
H3A H 0.503(3) 1.723(7) 0.016(2) 0.115(15) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C12 1.731(2) . ?
S1 C11 1.752(2) . ?
S2 C12 1.626(2) . ?
N1 C12 1.371(3) . ?
N1 C13 1.392(3) . ?
N1 C14 1.445(3) . ?
O3 C15 1.296(3) . ?
O3 H3A 0.83(4) . ?
C11 C10 1.335(3) . ?
C11 C13 1.467(3) . ?
O1 C13 1.207(3) . ?
C14 C15 1.497(3) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C2 C3 1.370(3) . ?
C2 C1 1.387(3) . ?
C2 H2 0.9300 . ?
C7 C8 1.345(3) . ?
C7 C1 1.460(3) . ?
C7 H7 0.9300 . ?
C1 C6 1.379(4) . ?
C8 C10 1.434(3) . ?
C8 C9 1.501(3) . ?
C15 O2 1.212(3) . ?
C6 C5 1.377(4) . ?
C6 H6 0.9300 . ?
C5 C4 1.367(4) . ?
C5 H5 0.9300 . ?
C3 C4 1.363(4) . ?
C3 H3 0.9300 . ?
C9 H9B 0.9600 . ?
C9 H9A 0.9600 . ?
C9 H9C 0.9600 . ?
C4 H4 0.9300 . ?
C10 H10 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C12 S1 C11 93.05(11) . . ?
C12 N1 C13 116.85(19) . . ?
C12 N1 C14 122.1(2) . . ?
C13 N1 C14 120.83(19) . . ?
C15 O3 H3A 111(3) . . ?
C10 C11 C13 120.1(2) . . ?
C10 C11 S1 130.65(18) . . ?
C13 C11 S1 109.27(17) . . ?
N1 C12 S2 125.94(18) . . ?
N1 C12 S1 110.36(17) . . ?
S2 C12 S1 123.70(13) . . ?
N1 C14 C15 111.2(2) . . ?
N1 C14 H14A 109.4 . . ?
C15 C14 H14A 109.4 . . ?
N1 C14 H14B 109.4 . . ?
C15 C14 H14B 109.4 . . ?
H14A C14 H14B 108.0 . . ?
C3 C2 C1 120.9(3) . . ?
C3 C2 H2 119.5 . . ?
C1 C2 H2 119.5 . . ?
C8 C7 C1 132.3(2) . . ?
C8 C7 H7 113.8 . . ?
C1 C7 H7 113.8 . . ?
O1 C13 N1 122.5(2) . . ?
O1 C13 C11 127.1(2) . . ?
N1 C13 C11 110.36(19) . . ?
C6 C1 C2 117.2(3) . . ?
C6 C1 C7 117.9(2) . . ?
C2 C1 C7 124.9(2) . . ?
C7 C8 C10 116.1(2) . . ?
C7 C8 C9 124.1(2) . . ?
C10 C8 C9 119.7(2) . . ?
O2 C15 O3 125.2(3) . . ?
O2 C15 C14 122.5(2) . . ?
O3 C15 C14 112.2(2) . . ?
C5 C6 C1 121.9(3) . . ?
C5 C6 H6 119.0 . . ?
C1 C6 H6 119.0 . . ?
C4 C5 C6 119.6(3) . . ?
C4 C5 H5 120.2 . . ?
C6 C5 H5 120.2 . . ?
C4 C3 C2 120.8(3) . . ?
C4 C3 H3 119.6 . . ?
C2 C3 H3 119.6 . . ?
C8 C9 H9B 109.5 . . ?
C8 C9 H9A 109.5 . . ?
H9B C9 H9A 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
C3 C4 C5 119.6(3) . . ?
C3 C4 H4 120.2 . . ?
C5 C4 H4 120.2 . . ?
C11 C10 C8 132.3(2) . . ?
C11 C10 H10 113.8 . . ?
C8 C10 H10 113.8 . . ?

_refine_diff_density_max         0.216
_refine_diff_density_min         -0.168
_refine_diff_density_rms         0.040



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: nitromethane '
_chemical_compound_source        synthetic
####################################################################### 
# 
# 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_EPR-Form-II
_database_code_depnum_ccdc_archive 'CCDC 1448700'
_audit_update_record             
;
2016-01-20 deposited with the CCDC.
2016-02-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
; 
 5-[(1Z, 2E)-2-methyl-3-phenylpropenylidene]-4-oxo2-thioxo-3-thiazolidineacetic acid 
;
_chemical_name_common            Epalrestat
_chemical_melting_point          494.57
_chemical_formula_moiety         'C15 H13 N O3 S2'
_chemical_formula_sum            'C15 H13 N O3 S2'
_chemical_formula_weight         319.38

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   13.7384(4)
_cell_length_b                   9.1063(3)
_cell_length_c                   24.1429(7)
_cell_angle_alpha                90
_cell_angle_beta                 100.747(3)
_cell_angle_gamma                90
_cell_volume                     2967.44(15)
_cell_formula_units_Z            8
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    6211
_cell_measurement_theta_min      3.2840
_cell_measurement_theta_max      71.6170

_exptl_crystal_description       Diamond
_exptl_crystal_colour            Red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.430
_exptl_crystal_F_000             1328
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    3.338
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.90137
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10378
_diffrn_reflns_av_unetI/netI     0.0526
_diffrn_reflns_av_R_equivalents  0.1006
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         3.727
_diffrn_reflns_theta_max         66.598
_diffrn_reflns_theta_full        66.598
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2625
_reflns_number_gt                2441
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0907P)²+3.7589P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0037(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2625
_refine_ls_number_parameters     193
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0583
_refine_ls_R_factor_gt           0.0558
_refine_ls_wR_factor_ref         0.1550
_refine_ls_wR_factor_gt          0.1514
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_restrained_S_all      1.087
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.64493(5) 1.04457(7) 0.54154(3) 0.0374(3) Uani 1 1 d . . . . .
S2 S 0.50782(5) 1.11933(8) 0.61835(3) 0.0463(3) Uani 1 1 d . . . . .
N1 N 0.66630(14) 0.9432(2) 0.64200(8) 0.0262(5) Uani 1 1 d . . . . .
O1 O 0.80170(13) 0.7927(2) 0.64912(7) 0.0371(5) Uani 1 1 d . . . . .
O3 O 0.6497(2) 1.0469(3) 0.78305(9) 0.0598(7) Uani 1 1 d . . . . .
H3A H 0.6725 1.1153 0.8035 0.090 Uiso 1 1 calc R U . . .
C7 C 0.92166(18) 0.8705(3) 0.46845(10) 0.0294(5) Uani 1 1 d . . . . .
H7 H 0.9597 0.8146 0.4967 0.035 Uiso 1 1 calc R U . . .
C10 C 0.82028(17) 0.8890(3) 0.53781(9) 0.0259(5) Uani 1 1 d . . . . .
H10 H 0.8678 0.8282 0.5587 0.031 Uiso 1 1 calc R U . . .
C13 C 0.74469(17) 0.8787(2) 0.62197(9) 0.0239(5) Uani 1 1 d . . . . .
C15 C 0.68115(19) 1.0561(3) 0.73473(11) 0.0350(6) Uani 1 1 d . . . . .
C8 C 0.83749(17) 0.9252(3) 0.48194(9) 0.0270(5) Uani 1 1 d . . . . .
C1 C 0.96303(18) 0.8841(3) 0.41732(10) 0.0281(5) Uani 1 1 d . . . . .
C2 C 0.9392(2) 0.9934(3) 0.37630(13) 0.0467(7) Uani 1 1 d . . . . .
H2 H 0.8922 1.0640 0.3804 0.056 Uiso 1 1 calc R U . . .
O2 O 0.72722(18) 1.1570(3) 0.72098(9) 0.0574(6) Uani 1 1 d . . . . .
C12 C 0.60561(19) 1.0335(3) 0.60571(11) 0.0302(5) Uani 1 1 d . . . . .
C14 C 0.65119(19) 0.9214(3) 0.69939(10) 0.0306(5) Uani 1 1 d . . . . .
H14B H 0.6900 0.8380 0.7159 0.037 Uiso 1 1 calc R U . . .
H14A H 0.5819 0.8999 0.6990 0.037 Uiso 1 1 calc R U . . .
C11 C 0.74654(17) 0.9293(2) 0.56420(9) 0.0247(5) Uani 1 1 d . . . . .
C6 C 1.03667(19) 0.7844(3) 0.40987(11) 0.0373(6) Uani 1 1 d . . . . .
H6 H 1.0560 0.7123 0.4370 0.045 Uiso 1 1 calc R U . . .
C4 C 1.0552(2) 0.8965(4) 0.32305(11) 0.0459(7) Uani 1 1 d . . . . .
H4 H 1.0850 0.8998 0.2915 0.055 Uiso 1 1 calc R U . . .
C9 C 0.7605(2) 1.0083(4) 0.44232(12) 0.0494(8) Uani 1 1 d . . . . .
H9C H 0.7692 1.1117 0.4494 0.074 Uiso 1 1 calc R U . . .
H9A H 0.6958 0.9793 0.4479 0.074 Uiso 1 1 calc R U . . .
H9B H 0.7668 0.9874 0.4042 0.074 Uiso 1 1 calc R U . . .
C3 C 0.9845(3) 0.9979(4) 0.32990(13) 0.0520(8) Uani 1 1 d . . . . .
H3 H 0.9668 1.0707 0.3029 0.062 Uiso 1 1 calc R U . . .
C5 C 1.0815(2) 0.7899(4) 0.36341(12) 0.0463(7) Uani 1 1 d . . . . .
H5 H 1.1297 0.7212 0.3593 0.056 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C12 1.736(3) . ?
S1 C11 1.751(2) . ?
S2 C12 1.632(3) . ?
N1 C12 1.366(3) . ?
N1 C13 1.390(3) . ?
N1 C14 1.452(3) . ?
O1 C13 1.210(3) . ?
O3 C15 1.320(3) . ?
O3 H3A 0.8200 . ?
C7 C8 1.353(3) . ?
C7 C1 1.457(3) . ?
C7 H7 0.9300 . ?
C10 C11 1.344(3) . ?
C10 C8 1.450(3) . ?
C10 H10 0.9300 . ?
C13 C11 1.474(3) . ?
C15 O2 1.197(4) . ?
C15 C14 1.507(4) . ?
C8 C9 1.494(4) . ?
C1 C6 1.396(4) . ?
C1 C2 1.399(4) . ?
C2 C3 1.380(4) . ?
C2 H2 0.9300 . ?
C14 H14B 0.9700 . ?
C14 H14A 0.9700 . ?
C6 C5 1.377(4) . ?
C6 H6 0.9300 . ?
C4 C3 1.373(5) . ?
C4 C5 1.375(5) . ?
C4 H4 0.9300 . ?
C9 H9C 0.9600 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C3 H3 0.9300 . ?
C5 H5 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C12 S1 C11 92.81(11) . . ?
C12 N1 C13 116.8(2) . . ?
C12 N1 C14 121.0(2) . . ?
C13 N1 C14 122.12(19) . . ?
C15 O3 H3A 109.5 . . ?
C8 C7 C1 131.2(2) . . ?
C8 C7 H7 114.4 . . ?
C1 C7 H7 114.4 . . ?
C11 C10 C8 130.3(2) . . ?
C11 C10 H10 114.8 . . ?
C8 C10 H10 114.8 . . ?
O1 C13 N1 123.4(2) . . ?
O1 C13 C11 126.2(2) . . ?
N1 C13 C11 110.39(19) . . ?
O2 C15 O3 124.8(2) . . ?
O2 C15 C14 124.8(2) . . ?
O3 C15 C14 110.4(2) . . ?
C7 C8 C10 115.8(2) . . ?
C7 C8 C9 124.6(2) . . ?
C10 C8 C9 119.5(2) . . ?
C6 C1 C2 116.8(2) . . ?
C6 C1 C7 117.4(2) . . ?
C2 C1 C7 125.7(2) . . ?
C3 C2 C1 121.0(3) . . ?
C3 C2 H2 119.5 . . ?
C1 C2 H2 119.5 . . ?
N1 C12 S2 126.4(2) . . ?
N1 C12 S1 110.68(18) . . ?
S2 C12 S1 122.90(15) . . ?
N1 C14 C15 110.9(2) . . ?
N1 C14 H14B 109.5 . . ?
C15 C14 H14B 109.5 . . ?
N1 C14 H14A 109.5 . . ?
C15 C14 H14A 109.5 . . ?
H14B C14 H14A 108.1 . . ?
C10 C11 C13 120.7(2) . . ?
C10 C11 S1 130.01(18) . . ?
C13 C11 S1 109.24(16) . . ?
C5 C6 C1 121.8(3) . . ?
C5 C6 H6 119.1 . . ?
C1 C6 H6 119.1 . . ?
C3 C4 C5 119.2(3) . . ?
C3 C4 H4 120.4 . . ?
C5 C4 H4 120.4 . . ?
C8 C9 H9C 109.5 . . ?
C8 C9 H9A 109.5 . . ?
H9C C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9C C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C4 C3 C2 120.9(3) . . ?
C4 C3 H3 119.5 . . ?
C2 C3 H3 119.5 . . ?
C4 C5 C6 120.3(3) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?

_refine_diff_density_max         0.609
_refine_diff_density_min         -0.413
_refine_diff_density_rms         0.088


_chemical_compound_source        synthetic
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: 2-propanol '
####################################################################### 
# 
# 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_EPR-Form-I
_database_code_depnum_ccdc_archive 'CCDC 1448701'
_audit_update_record             
;
2016-01-20 deposited with the CCDC.
2016-02-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
; 
 5-[(1Z, 2E)-2-methyl-3-phenylpropenylidene]-4-oxo2-thioxo-3-thiazolidineacetic acid 
;
_chemical_name_common            Epalrestat
_chemical_melting_point          494.94
_chemical_formula_moiety         'C15 H13 N O3 S2'
_chemical_formula_sum            'C15 H13 N O3 S2'
_chemical_formula_weight         319.38

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.1399(10)
_cell_length_b                   11.5584(14)
_cell_length_c                   16.1506(19)
_cell_angle_alpha                96.721(10)
_cell_angle_beta                 93.818(10)
_cell_angle_gamma                104.724(10)
_cell_volume                     1452.2(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    1668
_cell_measurement_theta_min      3.0200
_cell_measurement_theta_max      23.8880

_exptl_crystal_description       Block
_exptl_crystal_colour            Red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.461
_exptl_crystal_F_000             664
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.12
_exptl_absorpt_coefficient_mu    0.375
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.97491
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9766
_diffrn_reflns_av_unetI/netI     0.1306
_diffrn_reflns_av_R_equivalents  0.0593
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.760
_diffrn_reflns_theta_max         25.026
_diffrn_reflns_theta_full        25.026
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             5131
_reflns_number_gt                2548
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0063P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5131
_refine_ls_number_parameters     393
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1380
_refine_ls_R_factor_gt           0.0633
_refine_ls_wR_factor_ref         0.1084
_refine_ls_wR_factor_gt          0.0779
_refine_ls_goodness_of_fit_ref   0.983
_refine_ls_restrained_S_all      0.983
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S3 S 0.86226(14) 0.05389(11) 0.41155(8) 0.0577(4) Uani 1 1 d . . . . .
S4 S 1.06661(14) -0.10115(12) 0.34121(8) 0.0622(4) Uani 1 1 d . . . . .
S1 S 0.87108(16) 0.83392(12) 0.78866(8) 0.0634(4) Uani 1 1 d . . . . .
S2 S 0.94617(16) 0.63690(14) 0.67849(8) 0.0734(5) Uani 1 1 d . . . . .
N2 N 0.7305(4) -0.1411(3) 0.3147(2) 0.0400(9) Uani 1 1 d . . . . .
N1 N 0.9145(4) 0.6442(3) 0.8409(2) 0.0449(10) Uani 1 1 d . . . . .
O6 O 0.7769(4) -0.3299(3) 0.1333(2) 0.0655(10) Uani 1 1 d . . . . .
O4 O 0.4473(4) -0.1484(3) 0.2984(2) 0.0675(10) Uani 1 1 d . . . . .
O1 O 0.8679(4) 0.6673(3) 0.9779(2) 0.0650(10) Uani 1 1 d . . . . .
C22 C 0.4078(5) 0.2206(4) 0.4791(3) 0.0536(13) Uani 1 1 d . . . . .
H22 H 0.3085 0.1693 0.4501 0.064 Uiso 1 1 calc R U . . .
C25 C 0.5288(5) 0.0764(4) 0.4090(3) 0.0448(12) Uani 1 1 d . . . . .
H25 H 0.4172 0.0405 0.3859 0.054 Uiso 1 1 calc R U . . .
O3 O 0.8238(5) 0.3301(4) 0.7812(3) 0.0793(13) Uani 1 1 d . . . . .
O2 O 0.6469(4) 0.4438(3) 0.8027(2) 0.0726(11) Uani 1 1 d . . . . .
C11 C 0.8454(5) 0.8206(4) 0.8927(3) 0.0456(12) Uani 1 1 d . . . . .
C23 C 0.5501(5) 0.1856(4) 0.4647(3) 0.0469(12) Uani 1 1 d . . . . .
C13 C 0.8756(5) 0.7066(4) 0.9121(3) 0.0472(12) Uani 1 1 d . . . . .
C16 C 0.3806(5) 0.3238(4) 0.5316(3) 0.0454(12) Uani 1 1 d . . . . .
C10 C 0.8037(5) 0.8946(4) 0.9521(3) 0.0496(12) Uani 1 1 d . . . . .
H10 H 0.7984 0.8672 1.0040 0.060 Uiso 1 1 calc R U . . .
C15 C 0.7849(6) 0.4308(4) 0.8061(3) 0.0492(12) Uani 1 1 d . . . . .
C1 C 0.6797(5) 1.1690(5) 1.0475(3) 0.0559(14) Uani 1 1 d . . . . .
C28 C 0.5909(6) -0.0968(4) 0.3293(3) 0.0454(12) Uani 1 1 d . . . . .
C26 C 0.6421(5) 0.0171(4) 0.3846(3) 0.0459(12) Uani 1 1 d . . . . .
C7 C 0.7261(5) 1.0580(4) 1.0229(3) 0.0520(13) Uani 1 1 d . . . . .
H7 H 0.7287 1.0120 1.0663 0.062 Uiso 1 1 calc R U . . .
C29 C 0.7143(5) -0.2535(4) 0.2612(3) 0.0463(12) Uani 1 1 d . . . . .
H29B H 0.5980 -0.3035 0.2580 0.056 Uiso 1 1 calc R U . . .
H29A H 0.7894 -0.2967 0.2851 0.056 Uiso 1 1 calc R U . . .
O5 O 0.7709(5) -0.1380(4) 0.1501(2) 0.0960(14) Uani 1 1 d . . . . .
C30 C 0.7584(6) -0.2316(5) 0.1759(3) 0.0547(14) Uani 1 1 d . . . . .
C17 C 0.5011(6) 0.4120(5) 0.5823(3) 0.0665(16) Uani 1 1 d . . . . .
C14 C 0.9433(5) 0.5266(4) 0.8419(3) 0.0500(13) Uani 1 1 d . . . . .
H14B H 0.9742 0.5159 0.8990 0.060 Uiso 1 1 calc R U . . .
H14A H 1.0369 0.5197 0.8092 0.060 Uiso 1 1 calc R U . . .
C27 C 0.8845(5) -0.0720(4) 0.3512(3) 0.0463(12) Uani 1 1 d . . . . .
C12 C 0.9140(5) 0.6961(4) 0.7697(3) 0.0514(13) Uani 1 1 d . . . . .
C21 C 0.2130(5) 0.3317(4) 0.5295(3) 0.0539(13) Uani 1 1 d . . . . .
H21 H 0.1273 0.2731 0.4958 0.065 Uiso 1 1 calc R U . . .
C19 C 0.2969(6) 0.5127(4) 0.6252(3) 0.0579(14) Uani 1 1 d . . . . .
H19 H 0.2692 0.5770 0.6560 0.069 Uiso 1 1 calc R U . . .
C8 C 0.7657(5) 1.0079(4) 0.9510(3) 0.0489(12) Uani 1 1 d . . . . .
C6 C 0.6493(5) 1.1911(5) 1.1293(3) 0.0750(17) Uani 1 1 d . . . . .
H6 H 0.6624 1.1367 1.1658 0.090 Uiso 1 1 calc R U . . .
C18 C 0.4610(6) 0.5059(4) 0.6284(3) 0.0615(15) Uani 1 1 d . . . . .
H18 H 0.5461 0.5651 0.6619 0.074 Uiso 1 1 calc R U . . .
C2 C 0.6596(7) 1.2532(6) 0.9972(4) 0.097(2) Uani 1 1 d . . . . .
H2 H 0.6780 1.2412 0.9410 0.116 Uiso 1 1 calc R U . . .
C20 C 0.1733(6) 0.4250(5) 0.5767(3) 0.0634(15) Uani 1 1 d . . . . .
H20 H 0.0603 0.4285 0.5756 0.076 Uiso 1 1 calc R U . . .
C5 C 0.5994(7) 1.2925(6) 1.1586(4) 0.099(3) Uani 1 1 d . . . . .
H5 H 0.5772 1.3050 1.2142 0.119 Uiso 1 1 calc R U . . .
C24 C 0.7229(5) 0.2536(5) 0.5026(3) 0.088(2) Uani 1 1 d . . . . .
H24A H 0.7218 0.3342 0.5245 0.133 Uiso 1 1 calc R U . . .
H24B H 0.8017 0.2567 0.4607 0.133 Uiso 1 1 calc R U . . .
H24C H 0.7576 0.2140 0.5471 0.133 Uiso 1 1 calc R U . . .
C4 C 0.5825(8) 1.3741(6) 1.1070(6) 0.111(3) Uani 1 1 d . . . . .
H4 H 0.5500 1.4430 1.1268 0.133 Uiso 1 1 calc R U . . .
C3 C 0.6132(8) 1.3539(6) 1.0278(5) 0.119(3) Uani 1 1 d . . . . .
H3 H 0.6029 1.4099 0.9922 0.142 Uiso 1 1 calc R U . . .
C9 C 0.7647(8) 1.0619(5) 0.8720(3) 0.127(3) Uani 1 1 d . . . . .
H9C H 0.8700 1.1226 0.8719 0.190 Uiso 1 1 calc R U . . .
H9B H 0.6709 1.0979 0.8679 0.190 Uiso 1 1 calc R U . . .
H9A H 0.7524 1.0000 0.8251 0.190 Uiso 1 1 calc R U . . .
H6A H 0.790(6) -0.306(5) 0.078(3) 0.11(2) Uiso 1 1 d . . . . .
H3A H 0.744(7) 0.282(6) 0.757(4) 0.13(3) Uiso 1 1 d . . . . .
H17 H 0.614(6) 0.403(5) 0.592(3) 0.107(19) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S3 C27 1.711(4) . ?
S3 C26 1.745(4) . ?
S4 C27 1.615(4) . ?
S1 C12 1.714(5) . ?
S1 C11 1.727(4) . ?
S2 C12 1.616(4) . ?
N2 C27 1.356(5) . ?
N2 C28 1.383(4) . ?
N2 C29 1.445(5) . ?
N1 C12 1.358(5) . ?
N1 C13 1.382(5) . ?
N1 C14 1.438(5) . ?
O6 C30 1.306(5) . ?
O6 H6A 0.97(5) . ?
O4 C28 1.212(4) . ?
O1 C13 1.202(5) . ?
C22 C23 1.346(5) . ?
C22 C16 1.453(5) . ?
C22 H22 0.9300 . ?
C25 C26 1.336(5) . ?
C25 C23 1.425(5) . ?
C25 H25 0.9300 . ?
O3 C15 1.309(5) . ?
O3 H3A 0.78(6) . ?
O2 C15 1.169(4) . ?
C11 C10 1.329(5) . ?
C11 C13 1.465(6) . ?
C23 C24 1.477(5) . ?
C16 C17 1.364(6) . ?
C16 C21 1.389(5) . ?
C10 C8 1.421(5) . ?
C10 H10 0.9300 . ?
C15 C14 1.499(6) . ?
C1 C6 1.366(6) . ?
C1 C2 1.372(7) . ?
C1 C7 1.447(6) . ?
C28 C26 1.449(6) . ?
C7 C8 1.332(5) . ?
C7 H7 0.9300 . ?
C29 C30 1.480(6) . ?
C29 H29B 0.9700 . ?
C29 H29A 0.9700 . ?
O5 C30 1.187(5) . ?
C17 C18 1.364(6) . ?
C17 H17 0.95(4) . ?
C14 H14B 0.9700 . ?
C14 H14A 0.9700 . ?
C21 C20 1.366(5) . ?
C21 H21 0.9300 . ?
C19 C18 1.356(5) . ?
C19 C20 1.358(6) . ?
C19 H19 0.9300 . ?
C8 C9 1.486(6) . ?
C6 C5 1.379(7) . ?
C6 H6 0.9300 . ?
C18 H18 0.9300 . ?
C2 C3 1.362(7) . ?
C2 H2 0.9300 . ?
C20 H20 0.9300 . ?
C5 C4 1.356(9) . ?
C5 H5 0.9300 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C4 C3 1.324(8) . ?
C4 H4 0.9300 . ?
C3 H3 0.9300 . ?
C9 H9C 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9A 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C27 S3 C26 93.0(2) . . ?
C12 S1 C11 92.9(2) . . ?
C27 N2 C28 116.7(3) . . ?
C27 N2 C29 121.5(3) . . ?
C28 N2 C29 121.8(3) . . ?
C12 N1 C13 116.8(4) . . ?
C12 N1 C14 122.1(4) . . ?
C13 N1 C14 121.0(4) . . ?
C30 O6 H6A 102(3) . . ?
C23 C22 C16 131.9(4) . . ?
C23 C22 H22 114.0 . . ?
C16 C22 H22 114.0 . . ?
C26 C25 C23 130.9(4) . . ?
C26 C25 H25 114.6 . . ?
C23 C25 H25 114.6 . . ?
C15 O3 H3A 110(4) . . ?
C10 C11 C13 119.9(4) . . ?
C10 C11 S1 130.3(4) . . ?
C13 C11 S1 109.8(3) . . ?
C22 C23 C25 116.7(4) . . ?
C22 C23 C24 123.8(4) . . ?
C25 C23 C24 119.5(3) . . ?
O1 C13 N1 122.3(5) . . ?
O1 C13 C11 128.1(4) . . ?
N1 C13 C11 109.6(4) . . ?
C17 C16 C21 117.3(4) . . ?
C17 C16 C22 127.1(4) . . ?
C21 C16 C22 115.6(4) . . ?
C11 C10 C8 132.0(5) . . ?
C11 C10 H10 114.0 . . ?
C8 C10 H10 114.0 . . ?
O2 C15 O3 125.2(5) . . ?
O2 C15 C14 124.9(4) . . ?
O3 C15 C14 109.9(4) . . ?
C6 C1 C2 116.5(5) . . ?
C6 C1 C7 116.5(5) . . ?
C2 C1 C7 127.0(5) . . ?
O4 C28 N2 122.9(4) . . ?
O4 C28 C26 126.4(4) . . ?
N2 C28 C26 110.7(4) . . ?
C25 C26 C28 121.7(4) . . ?
C25 C26 S3 129.3(3) . . ?
C28 C26 S3 108.9(3) . . ?
C8 C7 C1 133.4(5) . . ?
C8 C7 H7 113.3 . . ?
C1 C7 H7 113.3 . . ?
N2 C29 C30 111.0(4) . . ?
N2 C29 H29B 109.4 . . ?
C30 C29 H29B 109.4 . . ?
N2 C29 H29A 109.4 . . ?
C30 C29 H29A 109.4 . . ?
H29B C29 H29A 108.0 . . ?
O5 C30 O6 125.4(5) . . ?
O5 C30 C29 124.1(4) . . ?
O6 C30 C29 110.5(5) . . ?
C18 C17 C16 122.0(4) . . ?
C18 C17 H17 118(3) . . ?
C16 C17 H17 120(3) . . ?
N1 C14 C15 109.9(3) . . ?
N1 C14 H14B 109.7 . . ?
C15 C14 H14B 109.7 . . ?
N1 C14 H14A 109.7 . . ?
C15 C14 H14A 109.7 . . ?
H14B C14 H14A 108.2 . . ?
N2 C27 S4 126.2(3) . . ?
N2 C27 S3 110.6(3) . . ?
S4 C27 S3 123.2(3) . . ?
N1 C12 S2 125.5(4) . . ?
N1 C12 S1 110.8(3) . . ?
S2 C12 S1 123.8(3) . . ?
C20 C21 C16 120.4(4) . . ?
C20 C21 H21 119.8 . . ?
C16 C21 H21 119.8 . . ?
C18 C19 C20 119.6(4) . . ?
C18 C19 H19 120.2 . . ?
C20 C19 H19 120.2 . . ?
C7 C8 C10 116.3(4) . . ?
C7 C8 C9 123.4(4) . . ?
C10 C8 C9 120.3(4) . . ?
C1 C6 C5 121.1(6) . . ?
C1 C6 H6 119.4 . . ?
C5 C6 H6 119.4 . . ?
C19 C18 C17 119.9(5) . . ?
C19 C18 H18 120.0 . . ?
C17 C18 H18 120.0 . . ?
C3 C2 C1 121.5(6) . . ?
C3 C2 H2 119.3 . . ?
C1 C2 H2 119.3 . . ?
C19 C20 C21 120.8(4) . . ?
C19 C20 H20 119.6 . . ?
C21 C20 H20 119.6 . . ?
C4 C5 C6 120.5(7) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C3 C4 C5 118.7(7) . . ?
C3 C4 H4 120.6 . . ?
C5 C4 H4 120.6 . . ?
C4 C3 C2 121.6(7) . . ?
C4 C3 H3 119.2 . . ?
C2 C3 H3 119.2 . . ?
C8 C9 H9C 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9C C9 H9B 109.5 . . ?
C8 C9 H9A 109.5 . . ?
H9C C9 H9A 109.5 . . ?
H9B C9 H9A 109.5 . . ?

_refine_diff_density_max         0.270
_refine_diff_density_min         -0.257
_refine_diff_density_rms         0.054



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: ethyl acetate : nitromethane '
_chemical_compound_source        synthetic
####################################################################### 
# 
# 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_EPR-ZZ-isomer
_database_code_depnum_ccdc_archive 'CCDC 1448702'
_audit_update_record             
;
2016-01-20 deposited with the CCDC.
2016-02-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
; 
 5-[(1Z, 2E)-2-methyl-3-phenylpropenylidene]-4-oxo2-thioxo-3-thiazolidineacetic acid  
;
_chemical_name_common            Epalrestat
_chemical_melting_point          451.97
_chemical_formula_moiety         'C15 H13 N O3 S2'
_chemical_formula_sum            'C15 H13 N O3 S2'
_chemical_formula_weight         319.38

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   11.4252(5)
_cell_length_b                   6.9479(3)
_cell_length_c                   19.4673(9)
_cell_angle_alpha                90
_cell_angle_beta                 102.898(5)
_cell_angle_gamma                90
_cell_volume                     1506.35(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    1693
_cell_measurement_theta_min      3.9640
_cell_measurement_theta_max      70.9620

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.408
_exptl_crystal_F_000             664
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.12
_exptl_absorpt_coefficient_mu    3.288
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.50714
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34i (release 04-08-2014 CrysAlis171 .NET)
(compiled Aug  4 2014,14:34:23)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5273
_diffrn_reflns_av_unetI/netI     0.0504
_diffrn_reflns_av_R_equivalents  0.0410
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         3.969
_diffrn_reflns_theta_max         66.601
_diffrn_reflns_theta_full        66.601
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2663
_reflns_number_gt                1910
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34i (release 04-08-2014 CrysAlis171 .NET)
(compiled Aug  4 2014,14:34:23)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34i (release 04-08-2014 CrysAlis171 .NET)
(compiled Aug  4 2014,14:34:23)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34i (release 04-08-2014 CrysAlis171 .NET)
(compiled Aug  4 2014,14:34:23)
;
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0835P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2663
_refine_ls_number_parameters     192
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0767
_refine_ls_R_factor_gt           0.0543
_refine_ls_wR_factor_ref         0.1604
_refine_ls_wR_factor_gt          0.1421
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_restrained_S_all      1.036
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.41626(7) 0.45325(11) 0.06938(5) 0.0531(3) Uani 1 1 d . . . . .
S2 S 0.21457(10) 0.48556(17) -0.05586(7) 0.0746(4) Uani 1 1 d . . . . .
O2 O 0.1340(2) 0.9138(4) 0.03842(13) 0.0562(6) Uani 1 1 d . . . . .
O1 O 0.4663(2) 0.9982(4) 0.07920(16) 0.0659(8) Uani 1 1 d . . . . .
N1 N 0.3440(2) 0.7764(4) 0.01145(15) 0.0454(6) Uani 1 1 d . . . . .
O3 O 0.0751(2) 1.0170(4) -0.07210(13) 0.0568(7) Uani 1 1 d . . . . .
H3A H 0.0112 1.0354 -0.0606 0.085 Uiso 1 1 calc R U . . .
C8 C 0.6385(3) 0.5347(5) 0.2138(2) 0.0517(8) Uani 1 1 d . . . . .
C15 C 0.1528(3) 0.9473(5) -0.01906(18) 0.0445(7) Uani 1 1 d . . . . .
C10 C 0.5802(3) 0.6798(5) 0.16533(19) 0.0483(8) Uani 1 1 d . . . . .
H10 H 0.6095 0.8042 0.1746 0.058 Uiso 1 1 calc R U . . .
C13 C 0.4374(3) 0.8328(4) 0.06827(18) 0.0448(7) Uani 1 1 d . . . . .
C11 C 0.4885(3) 0.6607(4) 0.10795(19) 0.0449(7) Uani 1 1 d . . . . .
C14 C 0.2742(3) 0.9176(5) -0.03545(19) 0.0483(8) Uani 1 1 d . . . . .
H14A H 0.2641 0.8745 -0.0838 0.058 Uiso 1 1 calc R U . . .
H14B H 0.3173 1.0390 -0.0307 0.058 Uiso 1 1 calc R U . . .
C12 C 0.3200(3) 0.5836(5) 0.0048(2) 0.0488(8) Uani 1 1 d . . . . .
C1 C 0.7958(3) 0.7663(6) 0.28088(19) 0.0529(8) Uani 1 1 d . . . . .
C7 C 0.7327(3) 0.5845(6) 0.2671(2) 0.0591(9) Uani 1 1 d . . . . .
H7 H 0.7607 0.4873 0.2995 0.071 Uiso 1 1 calc R U . . .
C5 C 0.8909(4) 1.0482(7) 0.2450(2) 0.0678(11) Uani 1 1 d . . . . .
H5 H 0.9131 1.1200 0.2096 0.081 Uiso 1 1 calc R U . . .
C2 C 0.8308(4) 0.8339(7) 0.3504(2) 0.0644(10) Uani 1 1 d . . . . .
H2 H 0.8135 0.7608 0.3869 0.077 Uiso 1 1 calc R U . . .
C9 C 0.5920(4) 0.3322(6) 0.2086(3) 0.0709(11) Uani 1 1 d . . . . .
H9A H 0.5079 0.3331 0.2087 0.106 Uiso 1 1 calc R U . . .
H9B H 0.6347 0.2591 0.2482 0.106 Uiso 1 1 calc R U . . .
H9C H 0.6034 0.2747 0.1658 0.106 Uiso 1 1 calc R U . . .
C6 C 0.8293(3) 0.8773(6) 0.2288(2) 0.0559(9) Uani 1 1 d . . . . .
H6 H 0.8099 0.8354 0.1823 0.067 Uiso 1 1 calc R U . . .
C4 C 0.9192(4) 1.1119(7) 0.3134(3) 0.0738(12) Uani 1 1 d . . . . .
H4 H 0.9587 1.2288 0.3240 0.089 Uiso 1 1 calc R U . . .
C3 C 0.8900(4) 1.0055(8) 0.3655(2) 0.0762(13) Uani 1 1 d . . . . .
H3 H 0.9103 1.0493 0.4118 0.091 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C12 1.730(4) . ?
S1 C11 1.745(3) . ?
S2 C12 1.635(3) . ?
O2 C15 1.208(4) . ?
O1 C13 1.202(4) . ?
N1 C12 1.368(4) . ?
N1 C13 1.410(4) . ?
N1 C14 1.451(4) . ?
O3 C15 1.296(4) . ?
O3 H3A 0.8200 . ?
C8 C7 1.362(6) . ?
C8 C10 1.438(5) . ?
C8 C9 1.500(5) . ?
C15 C14 1.505(4) . ?
C10 C11 1.357(5) . ?
C10 H10 0.9300 . ?
C13 C11 1.472(4) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C1 C6 1.394(5) . ?
C1 C2 1.404(5) . ?
C1 C7 1.449(5) . ?
C7 H7 0.9300 . ?
C5 C4 1.371(6) . ?
C5 C6 1.380(6) . ?
C5 H5 0.9300 . ?
C2 C3 1.370(7) . ?
C2 H2 0.9300 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C6 H6 0.9300 . ?
C4 C3 1.357(7) . ?
C4 H4 0.9300 . ?
C3 H3 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C12 S1 C11 92.48(16) . . ?
C12 N1 C13 116.5(3) . . ?
C12 N1 C14 122.2(3) . . ?
C13 N1 C14 121.3(3) . . ?
C15 O3 H3A 109.5 . . ?
C7 C8 C10 119.6(3) . . ?
C7 C8 C9 119.8(4) . . ?
C10 C8 C9 120.6(3) . . ?
O2 C15 O3 125.3(3) . . ?
O2 C15 C14 122.2(3) . . ?
O3 C15 C14 112.5(3) . . ?
C11 C10 C8 129.1(3) . . ?
C11 C10 H10 115.5 . . ?
C8 C10 H10 115.5 . . ?
O1 C13 N1 122.3(3) . . ?
O1 C13 C11 128.5(3) . . ?
N1 C13 C11 109.2(3) . . ?
C10 C11 C13 119.7(3) . . ?
C10 C11 S1 129.8(3) . . ?
C13 C11 S1 110.6(2) . . ?
N1 C14 C15 111.2(3) . . ?
N1 C14 H14A 109.4 . . ?
C15 C14 H14A 109.4 . . ?
N1 C14 H14B 109.4 . . ?
C15 C14 H14B 109.4 . . ?
H14A C14 H14B 108.0 . . ?
N1 C12 S2 125.2(3) . . ?
N1 C12 S1 111.2(2) . . ?
S2 C12 S1 123.6(2) . . ?
C6 C1 C2 116.8(4) . . ?
C6 C1 C7 123.6(3) . . ?
C2 C1 C7 119.5(4) . . ?
C8 C7 C1 129.6(4) . . ?
C8 C7 H7 115.2 . . ?
C1 C7 H7 115.2 . . ?
C4 C5 C6 119.8(4) . . ?
C4 C5 H5 120.1 . . ?
C6 C5 H5 120.1 . . ?
C3 C2 C1 121.3(4) . . ?
C3 C2 H2 119.4 . . ?
C1 C2 H2 119.4 . . ?
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 . . ?
C5 C6 C1 121.3(4) . . ?
C5 C6 H6 119.4 . . ?
C1 C6 H6 119.4 . . ?
C3 C4 C5 120.5(4) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
C4 C3 C2 120.3(4) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?

_refine_diff_density_max         0.310
_refine_diff_density_min         -0.292
_refine_diff_density_rms         0.060



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: ethanol : benzene'
_chemical_compound_source        synthetic
