# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1531870'
_audit_update_record             
;
2017-02-09 deposited with the CCDC.
2017-03-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
2-[(5Z)-5-[(E)-2-methyl-3-phenylprop-2-enylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]
_chemical_name_common            'Epalerstat. DMF solvate'
_chemical_melting_point          ?
_chemical_formula_moiety         ' C15 H13 N O3 S2, C3 H7 N O'
_chemical_formula_sum            'C18 H20 N2 O4 S2'
_chemical_formula_weight         392.48

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

_space_group_crystal_system      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                   7.6999(3)
_cell_length_b                   8.7601(3)
_cell_length_c                   15.1662(5)
_cell_angle_alpha                102.148(7)
_cell_angle_beta                 95.754(7)
_cell_angle_gamma                110.011(8)
_cell_volume                     923.03(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    93(2)
_cell_measurement_reflns_used    10720
_cell_measurement_theta_min      3.034
_cell_measurement_theta_max      68.209

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.412
_exptl_crystal_F_000             412
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    2.846
_shelx_estimated_absorpt_T_min   0.586
_shelx_estimated_absorpt_T_max   0.764
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.483
_exptl_absorpt_correction_T_max  0.752
_exptl_absorpt_process_details   'abscor T. Higashi RIGAKU'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      93(2)
_diffrn_radiation_wavelength     1.54187
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Rotating Anode X-ray'
_diffrn_measurement_device_type  'RIGAKU R-AXIS RAPID II'
_diffrn_measurement_method       ω-scan
_diffrn_detector_area_resol_mean 10.0
_diffrn_reflns_number            10720
_diffrn_reflns_av_unetI/netI     0.0401
_diffrn_reflns_av_R_equivalents  0.0401
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.034
_diffrn_reflns_theta_max         68.209
_diffrn_reflns_theta_full        67.687
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measured_fraction_theta_full 0.979
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_Laue_measured_fraction_full 0.979
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_point_group_measured_fraction_full 0.979
_reflns_number_total             3305
_reflns_number_gt                3013
_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       'RAPID AUTO'
_computing_cell_refinement       'RAPID AUTO'
_computing_data_reduction        'RAPID AUTO'
_computing_structure_solution    'SIR-2011 (Burla, 2011)'
_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)+(0.0501P)²+0.2441P] 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         3305
_refine_ls_number_parameters     254
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0386
_refine_ls_R_factor_gt           0.0357
_refine_ls_wR_factor_ref         0.0970
_refine_ls_wR_factor_gt          0.0945
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_restrained_S_all      1.090
_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
H18 H 0.700(3) 0.519(3) 0.4210(13) 0.027(5) Uiso 1 1 d . . . . .
C18 C 0.7048(3) 0.6320(2) 0.44839(12) 0.0264(4) Uani 1 1 d . . . . .
C17 C 0.3909(3) 0.5267(2) 0.35666(13) 0.0315(4) Uani 1 1 d . . . . .
H17A H 0.4174 0.4238 0.3395 0.047 Uiso 1 1 calc R U . . .
H17B H 0.3694 0.5649 0.3018 0.047 Uiso 1 1 calc R U . . .
H17C H 0.2785 0.5036 0.3846 0.047 Uiso 1 1 calc R U . . .
C16 C 0.5366(3) 0.8201(2) 0.45632(12) 0.0304(4) Uani 1 1 d . . . . .
H16A H 0.4436 0.8092 0.4966 0.046 Uiso 1 1 calc R U . . .
H16B H 0.4969 0.8584 0.4043 0.046 Uiso 1 1 calc R U . . .
H16C H 0.6592 0.9022 0.4908 0.046 Uiso 1 1 calc R U . . .
C15 C 0.7893(2) 1.2270(2) 0.35334(11) 0.0238(4) Uani 1 1 d . . . . .
C14 C 0.8829(2) 1.1097(2) 0.31152(11) 0.0225(4) Uani 1 1 d . . . . .
H14A H 1.0186 1.1747 0.3168 0.027 Uiso 1 1 calc R U . . .
H14B H 0.8706 1.0235 0.3460 0.027 Uiso 1 1 calc R U . . .
C13 C 0.8616(2) 1.0949(2) 0.14584(11) 0.0218(4) Uani 1 1 d . . . . .
C12 C 0.6430(2) 0.8750(2) 0.19108(11) 0.0223(4) Uani 1 1 d . . . . .
C11 C 0.5803(2) 0.8197(2) 0.09038(11) 0.0220(4) Uani 1 1 d . . . . .
C10 C 0.4277(2) 0.6779(2) 0.05225(12) 0.0228(4) Uani 1 1 d . . . . .
H10 H 0.365(3) 0.623(2) 0.0975(13) 0.030(5) Uiso 1 1 d . . . . .
C9 C 0.4492(2) 0.6381(2) -0.11782(12) 0.0246(4) Uani 1 1 d . . . . .
H9A H 0.4226 0.5374 -0.1679 0.037 Uiso 1 1 calc R U . . .
H9B H 0.5848 0.6897 -0.0933 0.037 Uiso 1 1 calc R U . . .
H9C H 0.4078 0.7187 -0.1411 0.037 Uiso 1 1 calc R U . . .
C8 C 0.3454(2) 0.5896(2) -0.04269(11) 0.0223(4) Uani 1 1 d . . . . .
C7 C 0.1789(2) 0.4584(2) -0.05624(12) 0.0215(4) Uani 1 1 d . . . . .
C6 C -0.0721(2) 0.2267(2) -0.30276(12) 0.0297(4) Uani 1 1 d . . . . .
H6 H -0.0695 0.2382 -0.3636 0.036 Uiso 1 1 calc R U . . .
H7 H 0.136(2) 0.432(2) -0.0004(13) 0.023(5) Uiso 1 1 d . . . . .
C5 C 0.0549(2) 0.3529(2) -0.22983(12) 0.0254(4) Uani 1 1 d . . . . .
H5 H 0.1425 0.4504 -0.2410 0.030 Uiso 1 1 calc R U . . .
C4 C 0.0540(2) 0.3366(2) -0.13964(11) 0.0212(4) Uani 1 1 d . . . . .
O4 O 0.84562(17) 0.74037(17) 0.50392(8) 0.0319(3) Uani 1 1 d . . . . .
H3A H 0.973(4) 1.301(3) 0.4602(18) 0.065(8) Uiso 1 1 d . . . . .
O3 O 0.86787(18) 1.31757(17) 0.43878(8) 0.0317(3) Uani 1 1 d . . . . .
C3 C -0.0815(2) 0.1921(2) -0.12673(12) 0.0238(4) Uani 1 1 d . . . . .
H3 H -0.0866 0.1799 -0.0662 0.029 Uiso 1 1 calc R U . . .
C2 C -0.2077(2) 0.0673(2) -0.19953(13) 0.0272(4) Uani 1 1 d . . . . .
H2 H -0.2975 -0.0297 -0.1890 0.033 Uiso 1 1 calc R U . . .
N2 N 0.5513(2) 0.65775(18) 0.42251(9) 0.0233(3) Uani 1 1 d . . . . .
S2 S 1.03661(6) 1.27285(6) 0.15661(3) 0.02748(14) Uani 1 1 d . . . . .
O2 O 0.65130(17) 1.23720(16) 0.31328(8) 0.0297(3) Uani 1 1 d . . . . .
S1 S 0.72773(6) 0.96347(5) 0.03972(3) 0.02356(14) Uani 1 1 d . . . . .
N1 N 0.79865(19) 1.02707(17) 0.21553(9) 0.0209(3) Uani 1 1 d . . . . .
C1 C -0.2021(2) 0.0846(2) -0.28810(13) 0.0291(4) Uani 1 1 d . . . . .
H1 H -0.2876 -0.0011 -0.3386 0.035 Uiso 1 1 calc R U . . .
O1 O 0.57577(17) 0.80401(16) 0.24712(8) 0.0272(3) Uani 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
C18 O4 1.250(2) . ?
C18 N2 1.315(2) . ?
C18 H18 0.97(2) . ?
C17 N2 1.463(2) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C16 N2 1.454(2) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C15 O2 1.210(2) . ?
C15 O3 1.325(2) . ?
C15 C14 1.517(2) . ?
C14 N1 1.452(2) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C13 N1 1.369(2) . ?
C13 S2 1.6381(18) . ?
C13 S1 1.7475(17) . ?
C12 O1 1.211(2) . ?
C12 N1 1.400(2) . ?
C12 C11 1.477(2) . ?
C11 C10 1.350(2) . ?
C11 S1 1.7518(17) . ?
C10 C8 1.444(2) . ?
C10 H10 0.99(2) . ?
C9 C8 1.507(2) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C8 C7 1.359(2) . ?
C7 C4 1.466(2) . ?
C7 H7 0.981(19) . ?
C6 C1 1.381(3) . ?
C6 C5 1.389(2) . ?
C6 H6 0.9500 . ?
C5 C4 1.405(2) . ?
C5 H5 0.9500 . ?
C4 C3 1.404(2) . ?
O3 H3A 0.91(3) . ?
C3 C2 1.382(2) . ?
C3 H3 0.9500 . ?
C2 C1 1.387(3) . ?
C2 H2 0.9500 . ?
C1 H1 0.9500 . ?

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
O4 C18 N2 123.87(17) . . ?
O4 C18 H18 121.9(11) . . ?
N2 C18 H18 114.3(11) . . ?
N2 C17 H17A 109.5 . . ?
N2 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
N2 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
N2 C16 H16A 109.5 . . ?
N2 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
N2 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O2 C15 O3 121.46(16) . . ?
O2 C15 C14 123.41(15) . . ?
O3 C15 C14 115.12(15) . . ?
N1 C14 C15 111.37(14) . . ?
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 C13 S2 126.53(13) . . ?
N1 C13 S1 110.34(12) . . ?
S2 C13 S1 123.12(10) . . ?
O1 C12 N1 122.67(15) . . ?
O1 C12 C11 127.41(16) . . ?
N1 C12 C11 109.91(14) . . ?
C10 C11 C12 119.65(16) . . ?
C10 C11 S1 130.57(14) . . ?
C12 C11 S1 109.76(12) . . ?
C11 C10 C8 131.07(17) . . ?
C11 C10 H10 114.1(11) . . ?
C8 C10 H10 114.8(11) . . ?
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 . . ?
C7 C8 C10 114.97(16) . . ?
C7 C8 C9 124.69(15) . . ?
C10 C8 C9 120.23(15) . . ?
C8 C7 C4 132.20(17) . . ?
C8 C7 H7 115.7(11) . . ?
C4 C7 H7 111.9(11) . . ?
C1 C6 C5 120.92(17) . . ?
C1 C6 H6 119.5 . . ?
C5 C6 H6 119.5 . . ?
C6 C5 C4 120.17(17) . . ?
C6 C5 H5 119.9 . . ?
C4 C5 H5 119.9 . . ?
C3 C4 C5 117.62(16) . . ?
C3 C4 C7 116.00(16) . . ?
C5 C4 C7 126.37(16) . . ?
C15 O3 H3A 112.7(16) . . ?
C2 C3 C4 121.92(16) . . ?
C2 C3 H3 119.0 . . ?
C4 C3 H3 119.0 . . ?
C3 C2 C1 119.45(17) . . ?
C3 C2 H2 120.3 . . ?
C1 C2 H2 120.3 . . ?
C18 N2 C16 121.10(15) . . ?
C18 N2 C17 121.64(16) . . ?
C16 N2 C17 117.24(15) . . ?
C13 S1 C11 92.77(8) . . ?
C13 N1 C12 117.16(14) . . ?
C13 N1 C14 122.53(14) . . ?
C12 N1 C14 120.27(14) . . ?
C6 C1 C2 119.91(17) . . ?
C6 C1 H1 120.0 . . ?
C2 C1 H1 120.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 C15 C14 N1 6.2(2) . . . . ?
O3 C15 C14 N1 -174.80(15) . . . . ?
O1 C12 C11 C10 2.5(3) . . . . ?
N1 C12 C11 C10 -177.88(15) . . . . ?
O1 C12 C11 S1 -178.45(15) . . . . ?
N1 C12 C11 S1 1.19(17) . . . . ?
C12 C11 C10 C8 -174.73(17) . . . . ?
S1 C11 C10 C8 6.4(3) . . . . ?
C11 C10 C8 C7 -173.68(19) . . . . ?
C11 C10 C8 C9 10.0(3) . . . . ?
C10 C8 C7 C4 -178.42(17) . . . . ?
C9 C8 C7 C4 -2.3(3) . . . . ?
C1 C6 C5 C4 0.7(3) . . . . ?
C6 C5 C4 C3 -1.6(3) . . . . ?
C6 C5 C4 C7 179.91(17) . . . . ?
C8 C7 C4 C3 164.08(18) . . . . ?
C8 C7 C4 C5 -17.4(3) . . . . ?
C5 C4 C3 C2 1.5(3) . . . . ?
C7 C4 C3 C2 -179.86(16) . . . . ?
C4 C3 C2 C1 -0.4(3) . . . . ?
O4 C18 N2 C16 1.4(3) . . . . ?
O4 C18 N2 C17 179.52(17) . . . . ?
N1 C13 S1 C11 2.05(13) . . . . ?
S2 C13 S1 C11 -178.10(12) . . . . ?
C10 C11 S1 C13 177.10(18) . . . . ?
C12 C11 S1 C13 -1.84(13) . . . . ?
S2 C13 N1 C12 178.39(13) . . . . ?
S1 C13 N1 C12 -1.76(19) . . . . ?
S2 C13 N1 C14 0.6(2) . . . . ?
S1 C13 N1 C14 -179.58(12) . . . . ?
O1 C12 N1 C13 -179.97(16) . . . . ?
C11 C12 N1 C13 0.4(2) . . . . ?
O1 C12 N1 C14 -2.1(2) . . . . ?
C11 C12 N1 C14 178.24(14) . . . . ?
C15 C14 N1 C13 89.41(18) . . . . ?
C15 C14 N1 C12 -88.34(19) . . . . ?
C5 C6 C1 C2 0.4(3) . . . . ?
C3 C2 C1 C6 -0.6(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C17 H17B O1 0.98 2.51 3.239(2) 130.8 .
C3 H3 S1 0.95 2.85 3.6609(18) 144.3 1_445
C16 H16B O1 0.98 2.51 3.195(2) 127.0 .
O3 H3A O4 0.91(3) 1.63(3) 2.5392(18) 177(3) 2_776
C9 H9B S1 0.98 2.60 3.2179(18) 121.4 .
C10 H10 O1 0.99(2) 2.509(18) 2.888(2) 102.3(12) .
C14 H14A S2 0.99 2.74 3.1269(18) 103.6 .
C16 H16C O4 0.98 2.36 2.771(2) 104.5 .

_refine_diff_density_max         0.397
_refine_diff_density_min         -0.237
_refine_diff_density_rms         0.053

####################################################################### 
# 
# 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_shelx_a
_database_code_depnum_ccdc_archive 'CCDC 1531872'
_audit_update_record             
;
2017-02-09 deposited with the CCDC.
2017-03-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        
2-[(5Z)-5-[(E)-2-methyl-3-phenylprop-2-enylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C8 H10 N4 O2, C15 H13 N O3 S2'
_chemical_formula_sum            'C23 H23 N5 O5 S2'
_chemical_formula_weight         513.58

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      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                   7.7900(4)
_cell_length_b                   8.4073(4)
_cell_length_c                   19.8594(10)
_cell_angle_alpha                84.159(3)
_cell_angle_beta                 88.907(2)
_cell_angle_gamma                62.877(3)
_cell_volume                     1151.06(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    2592
_cell_measurement_theta_min      4.49
_cell_measurement_theta_max      66.94

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.482
_exptl_crystal_F_000             536
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.265
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    2.503
_shelx_estimated_absorpt_T_min   0.557
_shelx_estimated_absorpt_T_max   0.825
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.685
_exptl_absorpt_correction_T_max  0.825
_exptl_absorpt_process_details   'Absorption was corrected by ABSCOR'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     1.54186
_diffrn_radiation_type           CuK\a
_diffrn_source                   'rotating anode X-ray tube'
_diffrn_measurement_device_type  'RIGAKU R-AXIS RAPID-II IP Area Detector'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13485
_diffrn_reflns_av_unetI/netI     0.0565
_diffrn_reflns_av_R_equivalents  0.0552
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         4.478
_diffrn_reflns_theta_max         68.172
_diffrn_reflns_theta_full        67.686
_diffrn_measured_fraction_theta_max 0.961
_diffrn_measured_fraction_theta_full 0.965
_diffrn_reflns_Laue_measured_fraction_max 0.961
_diffrn_reflns_Laue_measured_fraction_full 0.965
_diffrn_reflns_point_group_measured_fraction_max 0.961
_diffrn_reflns_point_group_measured_fraction_full 0.965
_reflns_number_total             4042
_reflns_number_gt                3130
_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       'PROCESS-AUTO (Rigaku, 1998)'
_computing_cell_refinement       'PROCESS-AUTO (Rigaku, 1998)'
_computing_data_reduction        'PROCESS-AUTO (Rigaku, 1998)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 2008)'
_computing_publication_material  'SHELXL-2014/07 (Sheldrick, 2014)'
_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)+(0.1342P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4042
_refine_ls_number_parameters     375
_refine_ls_number_restraints     48
_refine_ls_R_factor_all          0.0800
_refine_ls_R_factor_gt           0.0700
_refine_ls_wR_factor_ref         0.2230
_refine_ls_wR_factor_gt          0.2072
_refine_ls_goodness_of_fit_ref   1.193
_refine_ls_restrained_S_all      1.226
_refine_ls_shift/su_max          0.002
_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
N4A N 0.1500(11) -0.1298(7) 0.13735(19) 0.0438(19) Uani 0.515(5) 1 d D . P A 1
C20A C 0.1932(4) -0.0459(3) 0.08162(10) 0.0365(8) Uani 0.515(5) 1 d D . P A 1
C21A C 0.2332(5) -0.1658(3) 0.03300(11) 0.0391(8) Uani 0.515(5) 1 d D . P A 1
N5A N 0.221(2) -0.3129(9) 0.0566(3) 0.036(2) Uani 0.515(5) 1 d D U P A 1
C22A C 0.1679(10) -0.2846(7) 0.1197(2) 0.0472(19) Uani 0.515(5) 1 d D . P A 1
H22A H 0.144761 -0.367712 0.149766 0.057 Uiso 0.515(5) 1 calc R U P A 1
C19A C 0.1909(5) 0.1212(4) 0.06708(12) 0.0400(8) Uani 0.515(5) 1 d D . P A 1
O5A O 0.1420(9) 0.2387(7) 0.1059(3) 0.0394(16) Uani 0.515(5) 1 d D U P A 1
C23A C 0.0990(11) -0.0655(12) 0.2054(4) 0.054(2) Uani 0.515(5) 1 d D . P A 1
H23A H -0.019970 -0.070400 0.219428 0.082 Uiso 0.515(5) 1 calc R U P A 1
H23B H 0.079449 0.058548 0.203567 0.082 Uiso 0.515(5) 1 calc R U P A 1
H23C H 0.203861 -0.142410 0.238122 0.082 Uiso 0.515(5) 1 calc R U P A 1
N4B N 0.1550(11) -0.0513(8) 0.1490(2) 0.0437(19) Uani 0.485(5) 1 d D . P A 2
C20B C 0.1932(4) -0.0459(3) 0.08162(10) 0.0365(8) Uani 0.485(5) 1 d D . P A 2
C21B C 0.1909(5) 0.1212(4) 0.06708(12) 0.0400(8) Uani 0.485(5) 1 d D . P A 2
N5B N 0.1676(14) 0.2061(7) 0.1217(3) 0.052(3) Uani 0.485(5) 1 d D U P A 2
C22B C 0.1413(10) 0.0997(8) 0.1698(2) 0.046(2) Uani 0.485(5) 1 d D . P A 2
H22B H 0.114943 0.128180 0.215118 0.055 Uiso 0.485(5) 1 calc R U P A 2
C19B C 0.2332(5) -0.1658(3) 0.03300(11) 0.0391(8) Uani 0.485(5) 1 d D . P A 2
C23B C 0.1401(13) -0.1980(14) 0.1929(4) 0.053(2) Uani 0.485(5) 1 d . . P A 2
H23D H 0.123482 -0.168765 0.239837 0.080 Uiso 0.485(5) 1 calc R U P A 2
H23E H 0.258071 -0.310664 0.190028 0.080 Uiso 0.485(5) 1 calc R U P A 2
H23F H 0.028864 -0.211399 0.177682 0.080 Uiso 0.485(5) 1 calc R U P A 2
O5B O 0.230(2) -0.3124(10) 0.0421(5) 0.067(3) Uani 0.485(5) 1 d D . P A 2
S1 S -0.22802(13) 0.44748(12) 0.46755(4) 0.0438(3) Uani 1 1 d . . . . .
N1 N -0.2311(4) 0.4126(4) 0.34102(14) 0.0375(7) Uani 1 1 d . . . . .
O1 O 0.0332(3) 0.1400(3) 0.33047(12) 0.0460(6) Uani 1 1 d . . . . .
C1 C 0.6766(6) -0.3013(5) 0.74545(19) 0.0496(10) Uani 1 1 d . . . . .
H1 H 0.753406 -0.358196 0.785603 0.059 Uiso 1 1 calc R U . . .
S2 S -0.53189(13) 0.71760(13) 0.37059(5) 0.0474(3) Uani 1 1 d . . . . .
N2 N 0.2409(4) 0.1562(3) 0.00081(12) 0.0349(6) Uani 1 1 d D . . . .
O2 O -0.1534(3) 0.6471(3) 0.25053(12) 0.0480(6) Uani 1 1 d . . . . .
C2 C 0.7202(5) -0.3846(5) 0.68694(19) 0.0466(9) Uani 1 1 d . . . . .
H2 H 0.827184 -0.500381 0.686786 0.056 Uiso 1 1 calc R U . . .
C4 C 0.4515(5) -0.1339(5) 0.62705(17) 0.0383(8) Uani 1 1 d . . . . .
O4 O 0.3248(3) 0.0764(3) -0.10514(9) 0.0431(6) Uani 1 1 d D . . . .
C5 C 0.4078(5) -0.0483(5) 0.68710(19) 0.0477(9) Uani 1 1 d . . . . .
H5 H 0.301668 0.067859 0.687410 0.057 Uiso 1 1 calc R U . . .
C7 C 0.3488(5) -0.0554(5) 0.56132(19) 0.0405(8) Uani 1 1 d . . . . .
H7 H 0.419(5) -0.123(5) 0.5247(18) 0.045(10) Uiso 1 1 d . . . . .
C9 C 0.0382(5) 0.2047(5) 0.59401(18) 0.0502(9) Uani 1 1 d . . . . .
H9A H 0.067304 0.303935 0.600660 0.075 Uiso 1 1 calc R U . . .
H9B H 0.052057 0.132591 0.637428 0.075 Uiso 1 1 calc R U . . .
H9C H -0.094404 0.253287 0.576090 0.075 Uiso 1 1 calc R U . . .
C3 C 0.6104(5) -0.3017(5) 0.62875(18) 0.0416(9) Uani 1 1 d . . . . .
H3 H 0.644017 -0.360742 0.588665 0.050 Uiso 1 1 calc R U . . .
H3A H -0.343(9) 0.724(7) 0.147(3) 0.16(3) Uiso 1 1 d D . . . .
N3 N 0.2829(4) -0.1241(3) -0.03073(9) 0.0379(7) Uani 1 1 d D . . . .
O3 O -0.3708(4) 0.6569(4) 0.17592(14) 0.0527(7) Uani 1 1 d D . . . .
C6 C 0.5183(6) -0.1326(5) 0.74505(19) 0.0496(10) Uani 1 1 d . . . . .
H6 H 0.486373 -0.074927 0.785451 0.060 Uiso 1 1 calc R U . . .
C8 C 0.1773(5) 0.0874(5) 0.54416(17) 0.0402(8) Uani 1 1 d . . . . .
C10 C 0.1201(5) 0.1236(5) 0.47317(17) 0.0387(8) Uani 1 1 d . . . . .
H10 H 0.207866 0.038542 0.445436 0.046 Uiso 1 1 calc R U . . .
C11 C -0.0370(5) 0.2579(5) 0.43920(17) 0.0376(8) Uani 1 1 d . . . . .
C12 C -0.0652(5) 0.2558(5) 0.36560(17) 0.0368(8) Uani 1 1 d . . . . .
C13 C -0.3346(5) 0.5287(5) 0.38733(17) 0.0376(8) Uani 1 1 d . . . . .
C14 C -0.2934(5) 0.4448(5) 0.27028(17) 0.0440(9) Uani 1 1 d . . . . .
H14A H -0.431884 0.475340 0.267460 0.053 Uiso 1 1 calc R U . . .
H14B H -0.220225 0.333509 0.248229 0.053 Uiso 1 1 calc R U . . .
C15 C -0.2639(5) 0.5938(5) 0.23311(17) 0.0381(8) Uani 1 1 d . . . . .
C16 C 0.2855(4) 0.0347(4) -0.04798(10) 0.0345(8) Uani 1 1 d D . . . .
C17 C 0.2345(5) 0.3320(4) -0.01931(18) 0.0421(8) Uani 1 1 d . . . . .
H17A H 0.356142 0.314528 -0.040086 0.063 Uiso 1 1 calc R U . . .
H17B H 0.215874 0.396574 0.020742 0.063 Uiso 1 1 calc R U . . .
H17C H 0.127253 0.401994 -0.051992 0.063 Uiso 1 1 calc R U . . .
C18 C 0.3322(6) -0.2517(5) -0.08172(18) 0.0492(9) Uani 1 1 d . . . . .
H18A H 0.396431 -0.374784 -0.059413 0.074 Uiso 1 1 calc R U . . .
H18B H 0.419008 -0.232929 -0.114308 0.074 Uiso 1 1 calc R U . . .
H18C H 0.214222 -0.232609 -0.105500 0.074 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
N4A C22A 1.328(4) . ?
N4A C20A 1.370(3) . ?
N4A C23A 1.486(8) . ?
C20A C21A 1.395(2) . ?
C20A C19A 1.397(2) . ?
C21A N5A 1.323(3) . ?
C21A N3 1.3744(16) . ?
N5A C22A 1.322(4) . ?
C22A H22A 0.9500 . ?
C19A O5A 1.2320(10) . ?
C19A N2 1.406(3) . ?
C23A H23A 0.9800 . ?
C23A H23B 0.9800 . ?
C23A H23C 0.9800 . ?
N4B C22B 1.332(5) . ?
N4B C20B 1.367(4) . ?
N4B C23B 1.483(9) . ?
C20B C19B 1.395(2) . ?
C20B C21B 1.397(2) . ?
C21B N5B 1.323(4) . ?
C21B N2 1.406(3) . ?
N5B C22B 1.319(5) . ?
C22B H22B 0.9500 . ?
C19B O5B 1.241(2) . ?
C19B N3 1.3744(16) . ?
C23B H23D 0.9800 . ?
C23B H23E 0.9800 . ?
C23B H23F 0.9800 . ?
S1 C13 1.734(4) . ?
S1 C11 1.749(4) . ?
N1 C13 1.373(4) . ?
N1 C12 1.409(4) . ?
N1 C14 1.453(4) . ?
O1 C12 1.208(4) . ?
C1 C2 1.375(5) . ?
C1 C6 1.391(5) . ?
C1 H1 0.9500 . ?
S2 C13 1.638(4) . ?
N2 C16 1.402(3) . ?
N2 C17 1.470(4) . ?
O2 C15 1.206(4) . ?
C2 C3 1.372(5) . ?
C2 H2 0.9500 . ?
C4 C3 1.387(5) . ?
C4 C5 1.411(5) . ?
C4 C7 1.470(5) . ?
O4 C16 1.2283(10) . ?
C5 C6 1.372(5) . ?
C5 H5 0.9500 . ?
C7 C8 1.347(5) . ?
C7 H7 0.97(4) . ?
C9 C8 1.520(5) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C3 H3 0.9500 . ?
N3 C16 1.354(3) . ?
N3 C18 1.468(4) . ?
O3 C15 1.332(4) . ?
O3 H3A 0.86(2) . ?
C6 H6 0.9500 . ?
C8 C10 1.446(5) . ?
C10 C11 1.358(5) . ?
C10 H10 0.9500 . ?
C11 C12 1.485(4) . ?
C14 C15 1.495(5) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C22A N4A C20A 106.7(2) . . ?
C22A N4A C23A 125.8(5) . . ?
C20A N4A C23A 127.5(4) . . ?
N4A C20A C21A 103.32(15) . . ?
N4A C20A C19A 134.14(18) . . ?
C21A C20A C19A 122.40(18) . . ?
N5A C21A N3 127.9(2) . . ?
N5A C21A C20A 112.66(16) . . ?
N3 C21A C20A 119.47(15) . . ?
C22A N5A C21A 103.3(2) . . ?
N5A C22A N4A 114.0(3) . . ?
N5A C22A H22A 123.0 . . ?
N4A C22A H22A 123.0 . . ?
O5A C19A C20A 125.6(4) . . ?
O5A C19A N2 119.1(4) . . ?
C20A C19A N2 115.1(2) . . ?
N4A C23A H23A 109.5 . . ?
N4A C23A H23B 109.5 . . ?
H23A C23A H23B 109.5 . . ?
N4A C23A H23C 109.5 . . ?
H23A C23A H23C 109.5 . . ?
H23B C23A H23C 109.5 . . ?
C22B N4B C20B 106.6(2) . . ?
C22B N4B C23B 125.4(5) . . ?
C20B N4B C23B 127.9(5) . . ?
N4B C20B C19B 134.19(19) . . ?
N4B C20B C21B 103.38(17) . . ?
C19B C20B C21B 122.40(18) . . ?
N5B C21B C20B 112.4(2) . . ?
N5B C21B N2 131.7(3) . . ?
C20B C21B N2 115.1(2) . . ?
C22B N5B C21B 103.4(3) . . ?
N5B C22B N4B 114.0(3) . . ?
N5B C22B H22B 123.0 . . ?
N4B C22B H22B 123.0 . . ?
O5B C19B N3 115.2(6) . . ?
O5B C19B C20B 125.3(5) . . ?
N3 C19B C20B 119.47(15) . . ?
N4B C23B H23D 109.5 . . ?
N4B C23B H23E 109.5 . . ?
H23D C23B H23E 109.5 . . ?
N4B C23B H23F 109.5 . . ?
H23D C23B H23F 109.5 . . ?
H23E C23B H23F 109.5 . . ?
C13 S1 C11 93.35(16) . . ?
C13 N1 C12 117.0(3) . . ?
C13 N1 C14 121.8(3) . . ?
C12 N1 C14 121.1(3) . . ?
C2 C1 C6 119.1(4) . . ?
C2 C1 H1 120.5 . . ?
C6 C1 H1 120.5 . . ?
C16 N2 C19A 122.8(2) . . ?
C16 N2 C21B 122.8(2) . . ?
C16 N2 C17 118.6(2) . . ?
C19A N2 C17 118.5(2) . . ?
C21B N2 C17 118.5(2) . . ?
C3 C2 C1 120.5(4) . . ?
C3 C2 H2 119.8 . . ?
C1 C2 H2 119.8 . . ?
C3 C4 C5 117.8(4) . . ?
C3 C4 C7 116.8(3) . . ?
C5 C4 C7 125.3(3) . . ?
C6 C5 C4 120.1(4) . . ?
C6 C5 H5 119.9 . . ?
C4 C5 H5 119.9 . . ?
C8 C7 C4 131.9(3) . . ?
C8 C7 H7 116(2) . . ?
C4 C7 H7 112(2) . . ?
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 . . ?
C2 C3 C4 121.6(3) . . ?
C2 C3 H3 119.2 . . ?
C4 C3 H3 119.2 . . ?
C16 N3 C21A 121.07(18) . . ?
C16 N3 C19B 121.07(18) . . ?
C16 N3 C18 118.8(2) . . ?
C21A N3 C18 120.1(2) . . ?
C19B N3 C18 120.1(2) . . ?
C15 O3 H3A 117(5) . . ?
C5 C6 C1 120.9(4) . . ?
C5 C6 H6 119.5 . . ?
C1 C6 H6 119.5 . . ?
C7 C8 C10 116.5(3) . . ?
C7 C8 C9 124.8(3) . . ?
C10 C8 C9 118.7(3) . . ?
C11 C10 C8 131.3(3) . . ?
C11 C10 H10 114.3 . . ?
C8 C10 H10 114.3 . . ?
C10 C11 C12 119.8(3) . . ?
C10 C11 S1 130.6(3) . . ?
C12 C11 S1 109.6(3) . . ?
O1 C12 N1 123.3(3) . . ?
O1 C12 C11 127.3(3) . . ?
N1 C12 C11 109.4(3) . . ?
N1 C13 S2 125.6(3) . . ?
N1 C13 S1 110.5(3) . . ?
S2 C13 S1 123.8(2) . . ?
N1 C14 C15 112.1(3) . . ?
N1 C14 H14A 109.2 . . ?
C15 C14 H14A 109.2 . . ?
N1 C14 H14B 109.2 . . ?
C15 C14 H14B 109.2 . . ?
H14A C14 H14B 107.9 . . ?
O2 C15 O3 123.7(3) . . ?
O2 C15 C14 125.3(3) . . ?
O3 C15 C14 111.0(3) . . ?
O4 C16 N3 122.1(3) . . ?
O4 C16 N2 118.9(2) . . ?
N3 C16 N2 119.02(16) . . ?
N2 C17 H17A 109.5 . . ?
N2 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
N2 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
N3 C18 H18A 109.5 . . ?
N3 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
N3 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C22A N4A C20A C21A 0.6(7) . . . . ?
C23A N4A C20A C21A 178.8(7) . . . . ?
C22A N4A C20A C19A 176.1(4) . . . . ?
C23A N4A C20A C19A -5.7(11) . . . . ?
N4A C20A C21A N5A -1.4(8) . . . . ?
C19A C20A C21A N5A -177.6(7) . . . . ?
N4A C20A C21A N3 179.9(4) . . . . ?
C19A C20A C21A N3 3.7(5) . . . . ?
N3 C21A N5A C22A -179.8(5) . . . . ?
C20A C21A N5A C22A 1.6(11) . . . . ?
C21A N5A C22A N4A -1.2(12) . . . . ?
C20A N4A C22A N5A 0.4(10) . . . . ?
C23A N4A C22A N5A -177.9(9) . . . . ?
N4A C20A C19A O5A -0.9(8) . . . . ?
C21A C20A C19A O5A 173.9(5) . . . . ?
N4A C20A C19A N2 -177.8(5) . . . . ?
C21A C20A C19A N2 -2.9(4) . . . . ?
C22B N4B C20B C19B 175.7(5) . . . . ?
C23B N4B C20B C19B -1.6(11) . . . . ?
C22B N4B C20B C21B -2.4(7) . . . . ?
C23B N4B C20B C21B -179.7(7) . . . . ?
N4B C20B C21B N5B 4.3(7) . . . . ?
C19B C20B C21B N5B -174.1(5) . . . . ?
N4B C20B C21B N2 175.5(4) . . . . ?
C19B C20B C21B N2 -2.9(4) . . . . ?
C20B C21B N5B C22B -4.4(9) . . . . ?
N2 C21B N5B C22B -173.6(5) . . . . ?
C21B N5B C22B N4B 2.8(10) . . . . ?
C20B N4B C22B N5B -0.1(10) . . . . ?
C23B N4B C22B N5B 177.3(8) . . . . ?
N4B C20B C19B O5B 5.3(12) . . . . ?
C21B C20B C19B O5B -176.8(9) . . . . ?
N4B C20B C19B N3 -174.2(5) . . . . ?
C21B C20B C19B N3 3.7(5) . . . . ?
O5A C19A N2 C16 -175.6(4) . . . . ?
C20A C19A N2 C16 1.5(4) . . . . ?
O5A C19A N2 C17 0.6(6) . . . . ?
C20A C19A N2 C17 177.6(3) . . . . ?
N5B C21B N2 C16 170.5(7) . . . . ?
C20B C21B N2 C16 1.5(4) . . . . ?
N5B C21B N2 C17 -13.3(8) . . . . ?
C20B C21B N2 C17 177.6(3) . . . . ?
C6 C1 C2 C3 0.6(5) . . . . ?
C3 C4 C5 C6 -1.4(5) . . . . ?
C7 C4 C5 C6 -177.7(3) . . . . ?
C3 C4 C7 C8 168.3(3) . . . . ?
C5 C4 C7 C8 -15.4(6) . . . . ?
C1 C2 C3 C4 -0.9(5) . . . . ?
C5 C4 C3 C2 1.3(5) . . . . ?
C7 C4 C3 C2 177.9(3) . . . . ?
N5A C21A N3 C16 178.6(8) . . . . ?
C20A C21A N3 C16 -2.9(5) . . . . ?
N5A C21A N3 C18 -0.7(9) . . . . ?
C20A C21A N3 C18 177.8(3) . . . . ?
O5B C19B N3 C16 177.6(8) . . . . ?
C20B C19B N3 C16 -2.9(5) . . . . ?
O5B C19B N3 C18 -1.7(9) . . . . ?
C20B C19B N3 C18 177.8(3) . . . . ?
C4 C5 C6 C1 1.2(6) . . . . ?
C2 C1 C6 C5 -0.8(6) . . . . ?
C4 C7 C8 C10 -179.0(3) . . . . ?
C4 C7 C8 C9 -2.2(6) . . . . ?
C7 C8 C10 C11 -177.2(3) . . . . ?
C9 C8 C10 C11 5.8(5) . . . . ?
C8 C10 C11 C12 -176.3(3) . . . . ?
C8 C10 C11 S1 3.5(5) . . . . ?
C13 S1 C11 C10 177.3(3) . . . . ?
C13 S1 C11 C12 -2.9(2) . . . . ?
C13 N1 C12 O1 176.9(3) . . . . ?
C14 N1 C12 O1 -0.5(5) . . . . ?
C13 N1 C12 C11 -2.3(4) . . . . ?
C14 N1 C12 C11 -179.7(3) . . . . ?
C10 C11 C12 O1 4.0(5) . . . . ?
S1 C11 C12 O1 -175.8(3) . . . . ?
C10 C11 C12 N1 -176.8(3) . . . . ?
S1 C11 C12 N1 3.4(3) . . . . ?
C12 N1 C13 S2 -179.6(2) . . . . ?
C14 N1 C13 S2 -2.3(4) . . . . ?
C12 N1 C13 S1 0.1(3) . . . . ?
C14 N1 C13 S1 177.5(2) . . . . ?
C11 S1 C13 N1 1.7(2) . . . . ?
C11 S1 C13 S2 -178.5(2) . . . . ?
C13 N1 C14 C15 73.2(4) . . . . ?
C12 N1 C14 C15 -109.6(3) . . . . ?
N1 C14 C15 O2 21.1(5) . . . . ?
N1 C14 C15 O3 -161.5(3) . . . . ?
C21A N3 C16 O4 -178.2(3) . . . . ?
C19B N3 C16 O4 -178.2(3) . . . . ?
C18 N3 C16 O4 1.1(5) . . . . ?
C21A N3 C16 N2 1.5(4) . . . . ?
C19B N3 C16 N2 1.5(4) . . . . ?
C18 N3 C16 N2 -179.2(3) . . . . ?
C19A N2 C16 O4 178.9(3) . . . . ?
C21B N2 C16 O4 178.9(3) . . . . ?
C17 N2 C16 O4 2.7(4) . . . . ?
C19A N2 C16 N3 -0.8(5) . . . . ?
C21B N2 C16 N3 -0.8(5) . . . . ?
C17 N2 C16 N3 -177.0(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C23A H23B O5A 0.98 2.52 3.207(11) 127.4 .
O3 H3A O4 0.86(2) 1.86(3) 2.684(3) 161(6) 2_565
C17 H17B O5A 0.98 2.27 2.715(7) 106.3 .
C17 H17B N5B 0.98 2.57 3.013(6) 107.6 .
C2 H2 O2 0.95 2.55 3.258(4) 131.9 2_656
C5 H5 O2 0.95 2.57 3.391(4) 144.5 2_566
C9 H9C S1 0.98 2.49 3.173(4) 126.3 .
C10 H10 O1 0.95 2.54 2.901(4) 102.7 .
C14 H14B O1 0.99 2.42 2.831(5) 104.1 .
C18 H18B O4 0.98 2.38 2.724(4) 99.6 .

_refine_diff_density_max         0.644
_refine_diff_density_min         -0.484
_refine_diff_density_rms         0.084

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1531871'
_audit_update_record             
;
2017-02-09 deposited with the CCDC.
2017-03-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
2-[(5Z)-5-[(E)-2-methyl-3-phenylprop-2-enylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]a
_chemical_name_common            'epalerstat. 2 DMSO'
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H13 N O3 S2, 2(C2 H6 O S)'
_chemical_formula_sum            'C19 H25 N O5 S4'
_chemical_formula_weight         475.64

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      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                   8.0773(2)
_cell_length_b                   9.3224(2)
_cell_length_c                   16.0729(3)
_cell_angle_alpha                99.322(7)
_cell_angle_beta                 91.404(6)
_cell_angle_gamma                108.099(8)
_cell_volume                     1131.59(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    93(2)
_cell_measurement_reflns_used    13066
_cell_measurement_theta_min      5.073
_cell_measurement_theta_max      68.226

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.396
_exptl_crystal_F_000             500
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.130
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    4.118
_shelx_estimated_absorpt_T_min   0.617
_shelx_estimated_absorpt_T_max   0.684
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.369
_exptl_absorpt_correction_T_max  0.662
_exptl_absorpt_process_details   'abscor, T. Higashi RIGAKU'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      93(2)
_diffrn_radiation_wavelength     1.54187
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Rotating Anode X-ray'
_diffrn_measurement_device_type  'RIGAKU R-AXIS RAPID II'
_diffrn_measurement_method       ω-scan
_diffrn_detector_area_resol_mean 10.0
_diffrn_reflns_number            13066
_diffrn_reflns_av_unetI/netI     0.0698
_diffrn_reflns_av_R_equivalents  0.0507
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         5.073
_diffrn_reflns_theta_max         68.226
_diffrn_reflns_theta_full        67.687
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measured_fraction_theta_full 0.979
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_Laue_measured_fraction_full 0.979
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_point_group_measured_fraction_full 0.979
_reflns_number_total             4046
_reflns_number_gt                3170
_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       RAPID-AUTO
_computing_cell_refinement       RAPID-AUTO
_computing_data_reduction        RAPID-AUTO
_computing_structure_solution    'SIR-2011 (Burla, 2011)'
_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)+(0.0606P)²+0.0140P] 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         4046
_refine_ls_number_parameters     279
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0656
_refine_ls_R_factor_gt           0.0516
_refine_ls_wR_factor_ref         0.1359
_refine_ls_wR_factor_gt          0.1289
_refine_ls_goodness_of_fit_ref   1.160
_refine_ls_restrained_S_all      1.160
_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
C15 C -0.2437(4) 0.4556(3) 0.17932(19) 0.0284(7) Uani 1 1 d . . . . .
C14 C -0.2709(4) 0.3846(3) 0.25765(18) 0.0281(7) Uani 1 1 d . . . . .
H14A H -0.3974 0.3465 0.2652 0.034 Uiso 1 1 calc R U . . .
H14B H -0.2263 0.2961 0.2510 0.034 Uiso 1 1 calc R U . . .
C13 C -0.2470(4) 0.6073(3) 0.37039(18) 0.0255(7) Uani 1 1 d . . . . .
C12 C -0.0161(4) 0.5018(3) 0.36552(18) 0.0261(7) Uani 1 1 d . . . . .
C11 C 0.0496(4) 0.6319(3) 0.43712(18) 0.0271(7) Uani 1 1 d . . . . .
C10 C 0.2098(4) 0.6606(3) 0.47738(19) 0.0283(7) Uani 1 1 d . . . . .
H10 H 0.269(3) 0.587(3) 0.4550(17) 0.025(7) Uiso 1 1 d . . . . .
C9 C 0.2220(4) 0.8950(3) 0.58594(18) 0.0317(8) Uani 1 1 d . . . . .
H9A H 0.2850 0.9468 0.6409 0.048 Uiso 1 1 calc R U . . .
H9B H 0.1000 0.8411 0.5940 0.048 Uiso 1 1 calc R U . . .
H9C H 0.2264 0.9711 0.5498 0.048 Uiso 1 1 calc R U . . .
C8 C 0.3058(4) 0.7819(3) 0.54468(18) 0.0270(7) Uani 1 1 d . . . . .
C7 C 0.4702(4) 0.7830(3) 0.56577(19) 0.0284(7) Uani 1 1 d . . . . .
C6 C 0.7632(4) 1.1488(3) 0.70157(19) 0.0334(8) Uani 1 1 d . . . . .
H6 H 0.7746 1.2547 0.7151 0.040 Uiso 1 1 calc R U . . .
C5 C 0.6273(4) 1.0511(3) 0.64612(19) 0.0288(7) Uani 1 1 d . . . . .
H5 H 0.5460 1.0901 0.6215 0.035 Uiso 1 1 calc R U . . .
O5 O 0.8063(3) 1.0930(2) 0.15515(13) 0.0362(6) Uani 1 1 d . . . . .
C4 C 0.6080(4) 0.8946(3) 0.62589(18) 0.0264(7) Uani 1 1 d . . . . .
H4 H 0.504(3) 0.693(3) 0.5372(16) 0.025(7) Uiso 1 1 d . . . . .
O4 O 0.2994(2) 0.5329(2) 0.02445(12) 0.0336(5) Uani 1 1 d . . . . .
S4 S 0.66459(10) 0.96452(9) 0.10215(5) 0.0335(2) Uani 1 1 d . . . . .
C3 C 0.7318(4) 0.8417(4) 0.66294(18) 0.0304(7) Uani 1 1 d . . . . .
H3 H 0.7218 0.7361 0.6496 0.037 Uiso 1 1 calc R U . . .
O3 O -0.3695(3) 0.3827(2) 0.11879(15) 0.0319(5) Uani 1 1 d . . . . .
S3 S 0.23827(10) 0.37010(9) 0.04217(5) 0.0328(2) Uani 1 1 d . . . . .
C2 C 0.8679(4) 0.9405(4) 0.71839(19) 0.0322(8) Uani 1 1 d . . . . .
H2 H 0.9504 0.9029 0.7431 0.039 Uiso 1 1 calc R U . . .
O2 O -0.1182(3) 0.5635(2) 0.17269(12) 0.0317(5) Uani 1 1 d . . . . .
H3A H -0.350(5) 0.423(4) 0.074(2) 0.063(13) Uiso 1 1 d . . . . .
S2 S -0.43557(10) 0.62422(9) 0.34220(5) 0.0336(2) Uani 1 1 d . . . . .
C1 C 0.8834(4) 1.0941(4) 0.7377(2) 0.0346(8) Uani 1 1 d . . . . .
H1 H 0.9768 1.1624 0.7758 0.042 Uiso 1 1 calc R U . . .
S1 S -0.10525(10) 0.72819(9) 0.45385(5) 0.0306(2) Uani 1 1 d . . . . .
O1 O 0.0576(3) 0.4119(2) 0.33737(12) 0.0314(5) Uani 1 1 d . . . . .
N1 N -0.1804(3) 0.4962(3) 0.33238(14) 0.0239(6) Uani 1 1 d . . . . .
C19 C 0.4633(4) 1.0011(4) 0.1208(2) 0.0385(8) Uani 1 1 d . . . . .
H19A H 0.4496 1.0163 0.1817 0.058 Uiso 1 1 calc R U . . .
H19B H 0.3660 0.9135 0.0919 0.058 Uiso 1 1 calc R U . . .
H19C H 0.4636 1.0935 0.0991 0.058 Uiso 1 1 calc R U . . .
C18 C 0.6239(4) 0.8046(3) 0.1542(2) 0.0388(8) Uani 1 1 d . . . . .
H18A H 0.7265 0.7697 0.1535 0.058 Uiso 1 1 calc R U . . .
H18B H 0.5227 0.7214 0.1249 0.058 Uiso 1 1 calc R U . . .
H18C H 0.5999 0.8344 0.2128 0.058 Uiso 1 1 calc R U . . .
C17 C 0.0125(4) 0.2932(4) 0.0070(2) 0.0413(9) Uani 1 1 d . . . . .
H17A H -0.0473 0.3664 0.0294 0.062 Uiso 1 1 calc R U . . .
H17B H -0.0390 0.1965 0.0272 0.062 Uiso 1 1 calc R U . . .
H17C H -0.0006 0.2745 -0.0549 0.062 Uiso 1 1 calc R U . . .
C16 C 0.2131(4) 0.3923(4) 0.1524(2) 0.0392(8) Uani 1 1 d . . . . .
H16A H 0.3285 0.4320 0.1837 0.059 Uiso 1 1 calc R U . . .
H16B H 0.1488 0.2927 0.1668 0.059 Uiso 1 1 calc R U . . .
H16C H 0.1481 0.4644 0.1677 0.059 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
C15 O2 1.207(3) . ?
C15 O3 1.323(3) . ?
C15 C14 1.505(4) . ?
C14 N1 1.463(3) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C13 N1 1.376(3) . ?
C13 S2 1.639(3) . ?
C13 S1 1.736(3) . ?
C12 O1 1.209(3) . ?
C12 N1 1.401(3) . ?
C12 C11 1.481(4) . ?
C11 C10 1.361(4) . ?
C11 S1 1.754(3) . ?
C10 C8 1.438(4) . ?
C10 H10 0.98(3) . ?
C9 C8 1.500(4) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C8 C7 1.359(4) . ?
C7 C4 1.469(4) . ?
C7 H4 1.01(3) . ?
C6 C5 1.378(4) . ?
C6 C1 1.384(4) . ?
C6 H6 0.9500 . ?
C5 C4 1.401(4) . ?
C5 H5 0.9500 . ?
O5 S4 1.497(2) . ?
C4 C3 1.403(4) . ?
O4 S3 1.520(2) . ?
S4 C18 1.773(3) . ?
S4 C19 1.785(3) . ?
C3 C2 1.381(4) . ?
C3 H3 0.9500 . ?
O3 H3A 0.87(4) . ?
S3 C16 1.775(3) . ?
S3 C17 1.779(3) . ?
C2 C1 1.381(4) . ?
C2 H2 0.9500 . ?
C1 H1 0.9500 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 C15 O3 124.8(3) . . ?
O2 C15 C14 123.2(3) . . ?
O3 C15 C14 112.0(3) . . ?
N1 C14 C15 110.9(2) . . ?
N1 C14 H14A 109.5 . . ?
C15 C14 H14A 109.5 . . ?
N1 C14 H14B 109.5 . . ?
C15 C14 H14B 109.5 . . ?
H14A C14 H14B 108.1 . . ?
N1 C13 S2 125.2(2) . . ?
N1 C13 S1 110.9(2) . . ?
S2 C13 S1 123.85(17) . . ?
O1 C12 N1 123.1(3) . . ?
O1 C12 C11 126.8(3) . . ?
N1 C12 C11 110.1(2) . . ?
C10 C11 C12 119.8(3) . . ?
C10 C11 S1 130.6(2) . . ?
C12 C11 S1 109.6(2) . . ?
C11 C10 C8 130.7(3) . . ?
C11 C10 H10 113.4(15) . . ?
C8 C10 H10 115.9(15) . . ?
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 . . ?
C7 C8 C10 115.2(3) . . ?
C7 C8 C9 125.1(3) . . ?
C10 C8 C9 119.7(3) . . ?
C8 C7 C4 130.1(3) . . ?
C8 C7 H4 116.0(15) . . ?
C4 C7 H4 113.9(15) . . ?
C5 C6 C1 120.6(3) . . ?
C5 C6 H6 119.7 . . ?
C1 C6 H6 119.7 . . ?
C6 C5 C4 120.4(3) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?
C5 C4 C3 118.1(3) . . ?
C5 C4 C7 124.1(3) . . ?
C3 C4 C7 117.8(3) . . ?
O5 S4 C18 106.87(13) . . ?
O5 S4 C19 107.30(14) . . ?
C18 S4 C19 96.88(15) . . ?
C2 C3 C4 121.2(3) . . ?
C2 C3 H3 119.4 . . ?
C4 C3 H3 119.4 . . ?
C15 O3 H3A 111(2) . . ?
O4 S3 C16 104.51(13) . . ?
O4 S3 C17 106.26(14) . . ?
C16 S3 C17 97.39(15) . . ?
C1 C2 C3 119.7(3) . . ?
C1 C2 H2 120.2 . . ?
C3 C2 H2 120.2 . . ?
C2 C1 C6 120.1(3) . . ?
C2 C1 H1 119.9 . . ?
C6 C1 H1 119.9 . . ?
C13 S1 C11 92.86(13) . . ?
C13 N1 C12 116.5(2) . . ?
C13 N1 C14 121.7(2) . . ?
C12 N1 C14 121.6(2) . . ?
S4 C19 H19A 109.5 . . ?
S4 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
S4 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
S4 C18 H18A 109.5 . . ?
S4 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
S4 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
S3 C17 H17A 109.5 . . ?
S3 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
S3 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
S3 C16 H16A 109.5 . . ?
S3 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
S3 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 C15 C14 N1 25.9(4) . . . . ?
O3 C15 C14 N1 -156.3(2) . . . . ?
O1 C12 C11 C10 1.0(5) . . . . ?
N1 C12 C11 C10 -178.4(3) . . . . ?
O1 C12 C11 S1 -179.9(3) . . . . ?
N1 C12 C11 S1 0.7(3) . . . . ?
C12 C11 C10 C8 176.6(3) . . . . ?
S1 C11 C10 C8 -2.3(5) . . . . ?
C11 C10 C8 C7 -175.0(3) . . . . ?
C11 C10 C8 C9 5.1(5) . . . . ?
C10 C8 C7 C4 174.8(3) . . . . ?
C9 C8 C7 C4 -5.3(5) . . . . ?
C1 C6 C5 C4 0.4(5) . . . . ?
C6 C5 C4 C3 -0.7(4) . . . . ?
C6 C5 C4 C7 -178.2(3) . . . . ?
C8 C7 C4 C5 -29.3(5) . . . . ?
C8 C7 C4 C3 153.1(3) . . . . ?
C5 C4 C3 C2 0.6(4) . . . . ?
C7 C4 C3 C2 178.3(3) . . . . ?
C4 C3 C2 C1 -0.3(4) . . . . ?
C3 C2 C1 C6 0.0(5) . . . . ?
C5 C6 C1 C2 0.0(5) . . . . ?
N1 C13 S1 C11 1.1(2) . . . . ?
S2 C13 S1 C11 -179.4(2) . . . . ?
C10 C11 S1 C13 177.9(3) . . . . ?
C12 C11 S1 C13 -1.0(2) . . . . ?
S2 C13 N1 C12 179.6(2) . . . . ?
S1 C13 N1 C12 -0.9(3) . . . . ?
S2 C13 N1 C14 3.6(4) . . . . ?
S1 C13 N1 C14 -176.9(2) . . . . ?
O1 C12 N1 C13 -179.3(3) . . . . ?
C11 C12 N1 C13 0.2(3) . . . . ?
O1 C12 N1 C14 -3.3(4) . . . . ?
C11 C12 N1 C14 176.1(2) . . . . ?
C15 C14 N1 C13 77.7(3) . . . . ?
C15 C14 N1 C12 -98.1(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C14 H14B O5 0.99 2.33 3.185(3) 144.5 1_445
C1 H1 O2 0.95 2.44 3.237(4) 140.8 2_676
O3 H3A O4 0.87(4) 1.72(4) 2.572(3) 167(4) 2_565
O3 H3A S3 0.87(4) 2.86(4) 3.698(3) 164(3) 2_565
C19 H19C O3 0.98 2.57 3.396(4) 141.4 1_665
C18 H18B O4 0.98 2.43 3.396(4) 167.4 .
C17 H17B O5 0.98 2.60 3.410(4) 140.6 1_445
C16 H16C O2 0.98 2.59 3.513(4) 157.2 .
C2 H2 O5 0.95 2.51 3.407(4) 157.0 2_776
C3 H3 O1 0.95 2.59 3.313(3) 132.9 2_666
C9 H9B S1 0.98 2.63 3.165(3) 114.8 .
C10 H10 O1 0.98(3) 2.50(3) 2.891(4) 103.3(17) .
C14 H14B O1 0.99 2.48 2.838(3) 100.6 .

_refine_diff_density_max         0.633
_refine_diff_density_min         -0.361
_refine_diff_density_rms         0.078

