# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_TCZ-BROM
_database_code_depnum_ccdc_archive 'CCDC 2285606'
loop_
_audit_author_name
_audit_author_address
'Tejender Thakur'
;CSIR Central Drug Research Institute
India
;
_audit_update_record             
;
2023-07-31 deposited with the CCDC.	2023-11-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/2
_shelx_SHELXL_version_number     2019/2
_chemical_name_systematic        ?
_chemical_name_common            'Tioconazole Hydrobromide Salt'
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H14 Cl3 N2 O S, Br'
_chemical_formula_sum            'C16 H14 Br Cl3 N2 O S'
_chemical_formula_weight         468.61

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'
Cl Cl 0.3639 0.7018 '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'
Br Br -0.6763 1.2805 '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                   35.9750(19)
_cell_length_b                   6.3852(4)
_cell_length_c                   17.1343(9)
_cell_angle_alpha                90
_cell_angle_beta                 104.246(3)
_cell_angle_gamma                90
_cell_volume                     3814.8(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9573
_cell_measurement_theta_min      2.66
_cell_measurement_theta_max      78.09
_exptl_crystal_description       block
_exptl_crystal_colour            colourless

_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.632
_exptl_crystal_F_000             1872
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.140
_exptl_absorpt_coefficient_mu    7.882
_shelx_estimated_absorpt_T_min   0.201
_shelx_estimated_absorpt_T_max   0.405
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4192
_exptl_absorpt_correction_T_max  0.7542
_exptl_absorpt_process_details   SADABS-2016/2
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            54812
_diffrn_reflns_av_unetI/netI     0.0356
_diffrn_reflns_av_R_equivalents  0.1046
_diffrn_reflns_limit_h_min       -45
_diffrn_reflns_limit_h_max       45
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         5.073
_diffrn_reflns_theta_max         79.212
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4093
_reflns_number_gt                3106
_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       'PROTEUM2,version 2016.1-RC1'
_computing_cell_refinement       'Bruker SAINT v8.37a'
_computing_data_reduction        'Bruker SAINT v8.37a'
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'
_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)+(0.0594P)²+7.5171P] 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         4093
_refine_ls_number_parameters     231
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0675
_refine_ls_R_factor_gt           0.0478
_refine_ls_wR_factor_ref         0.1306
_refine_ls_wR_factor_gt          0.1178
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.040
_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
C1 C 0.40907(9) 0.6258(6) 0.49892(18) 0.0443(7) Uani 1 1 d . . . . .
C2 C 0.43808(11) 0.7623(6) 0.4958(2) 0.0531(9) Uani 1 1 d . . . . .
C3 C 0.46368(12) 0.7268(7) 0.4490(2) 0.0652(11) Uani 1 1 d . . . . .
H3 H 0.482989 0.822962 0.448137 0.078 Uiso 1 1 calc R U . . .
C4 C 0.46023(10) 0.5513(7) 0.4048(2) 0.0589(10) Uani 1 1 d . . . . .
C5 C 0.43170(14) 0.4140(9) 0.4044(3) 0.0920(18) Uani 1 1 d . . . . .
H5 H 0.429143 0.294645 0.372393 0.110 Uiso 1 1 calc R U . . .
C6 C 0.40623(13) 0.4512(8) 0.4516(3) 0.0836(16) Uani 1 1 d . . . . .
H6 H 0.386732 0.355264 0.451148 0.100 Uiso 1 1 calc R U . . .
C7 C 0.38051(9) 0.6615(5) 0.54900(18) 0.0425(7) Uani 1 1 d . . . . .
H7 H 0.389549 0.774518 0.587700 0.051 Uiso 1 1 calc R U . . .
C8 C 0.34180(9) 0.7200(6) 0.4943(2) 0.0497(8) Uani 1 1 d . . . . .
H8A H 0.343804 0.853858 0.468928 0.060 Uiso 1 1 calc R U . . .
H8B H 0.334249 0.615536 0.452311 0.060 Uiso 1 1 calc R U . . .
C9 C 0.28887(9) 0.5787(6) 0.5458(2) 0.0497(8) Uani 1 1 d . . . . .
H9 H 0.286497 0.453025 0.517631 0.060 Uiso 1 1 calc R U . . .
C10 C 0.28067(11) 0.8276(7) 0.6275(2) 0.0648(11) Uani 1 1 d . . . . .
H10 H 0.271312 0.902274 0.665173 0.078 Uiso 1 1 calc R U . . .
C11 C 0.30793(10) 0.8905(7) 0.5923(2) 0.0598(9) Uani 1 1 d . . . . .
H11 H 0.321223 1.016663 0.600885 0.072 Uiso 1 1 calc R U . . .
C12 C 0.40155(10) 0.4453(6) 0.6652(2) 0.0558(9) Uani 1 1 d . . . . .
H12A H 0.408808 0.577900 0.692282 0.067 Uiso 1 1 calc R U . . .
H12B H 0.424384 0.379016 0.656120 0.067 Uiso 1 1 calc R U . . .
C13 C 0.39717(11) 0.1261(6) 0.7506(2) 0.0524(8) Uani 1 1 d . . . . .
C14 C 0.38301(10) 0.3067(6) 0.7151(2) 0.0487(8) Uani 1 1 d . . . . .
C15 C 0.34706(11) 0.3506(7) 0.7317(2) 0.0599(9) Uani 1 1 d . . . . .
H15 H 0.333043 0.471035 0.713557 0.072 Uiso 1 1 calc R U . . .
C16 C 0.33493(12) 0.2023(7) 0.7760(2) 0.0647(10) Uani 1 1 d . . . . .
H16 H 0.311716 0.207539 0.790700 0.078 Uiso 1 1 calc R U . . .
N1 N 0.31262(7) 0.7332(5) 0.54074(16) 0.0462(6) Uani 1 1 d . . . . .
N2 N 0.26908(8) 0.6344(6) 0.59813(19) 0.0572(8) Uani 1 1 d . . . . .
O1 O 0.37405(6) 0.4777(4) 0.59057(13) 0.0451(5) Uani 1 1 d . . . . .
Cl1A Cl 0.4340(5) 1.0126(7) 0.5302(9) 0.085(3) Uani 0.45(2) 1 d . . P . .
Cl1B Cl 0.4501(3) 0.9694(16) 0.5676(8) 0.084(3) Uani 0.55(2) 1 d . . P . .
Cl2 Cl 0.49209(3) 0.5034(2) 0.34520(7) 0.0861(4) Uani 1 1 d . . . . .
Cl3 Cl 0.44049(3) 0.01320(18) 0.75166(7) 0.0728(3) Uani 1 1 d . . . . .
S1 S 0.36745(3) 0.00459(17) 0.80177(6) 0.0634(3) Uani 1 1 d . . . . .
Br1 Br 0.20864(2) 0.28551(7) 0.62101(3) 0.07017(18) Uani 1 1 d . . . . .
H2N H 0.2527(13) 0.557(7) 0.609(3) 0.070(14) 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
C1 C6 1.367(6) . ?
C1 C2 1.371(5) . ?
C1 C7 1.509(4) . ?
C2 C3 1.380(5) . ?
C2 Cl1A 1.723(6) . ?
C2 Cl1B 1.786(5) . ?
C3 C4 1.341(6) . ?
C3 H3 0.9300 . ?
C4 C5 1.348(6) . ?
C4 Cl2 1.740(3) . ?
C5 C6 1.384(5) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 O1 1.421(4) . ?
C7 C8 1.521(4) . ?
C7 H7 0.9800 . ?
C8 N1 1.467(4) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 N1 1.322(4) . ?
C9 N2 1.323(4) . ?
C9 H9 0.9300 . ?
C10 C11 1.334(6) . ?
C10 N2 1.359(6) . ?
C10 H10 0.9300 . ?
C11 N1 1.375(5) . ?
C11 H11 0.9300 . ?
C12 O1 1.426(4) . ?
C12 C14 1.497(5) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.344(5) . ?
C13 Cl3 1.713(4) . ?
C13 S1 1.724(4) . ?
C14 C15 1.418(5) . ?
C15 C16 1.352(6) . ?
C15 H15 0.9300 . ?
C16 S1 1.704(5) . ?
C16 H16 0.9300 . ?
N2 H2N 0.83(5) . ?
Cl1A Cl1B 0.798(4) . ?

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
C6 C1 C2 116.2(3) . . ?
C6 C1 C7 119.9(3) . . ?
C2 C1 C7 123.9(3) . . ?
C1 C2 C3 122.8(4) . . ?
C1 C2 Cl1A 116.6(4) . . ?
C3 C2 Cl1A 118.4(3) . . ?
C1 C2 Cl1B 120.1(3) . . ?
C3 C2 Cl1B 116.0(3) . . ?
Cl1A C2 Cl1B 26.23(17) . . ?
C4 C3 C2 118.9(4) . . ?
C4 C3 H3 120.6 . . ?
C2 C3 H3 120.6 . . ?
C3 C4 C5 120.7(3) . . ?
C3 C4 Cl2 119.7(3) . . ?
C5 C4 Cl2 119.5(3) . . ?
C4 C5 C6 119.9(4) . . ?
C4 C5 H5 120.1 . . ?
C6 C5 H5 120.1 . . ?
C1 C6 C5 121.5(4) . . ?
C1 C6 H6 119.2 . . ?
C5 C6 H6 119.2 . . ?
O1 C7 C1 112.2(3) . . ?
O1 C7 C8 105.9(3) . . ?
C1 C7 C8 109.6(3) . . ?
O1 C7 H7 109.7 . . ?
C1 C7 H7 109.7 . . ?
C8 C7 H7 109.7 . . ?
N1 C8 C7 110.4(3) . . ?
N1 C8 H8A 109.6 . . ?
C7 C8 H8A 109.6 . . ?
N1 C8 H8B 109.6 . . ?
C7 C8 H8B 109.6 . . ?
H8A C8 H8B 108.1 . . ?
N1 C9 N2 108.0(3) . . ?
N1 C9 H9 126.0 . . ?
N2 C9 H9 126.0 . . ?
C11 C10 N2 107.4(3) . . ?
C11 C10 H10 126.3 . . ?
N2 C10 H10 126.3 . . ?
C10 C11 N1 106.9(4) . . ?
C10 C11 H11 126.5 . . ?
N1 C11 H11 126.5 . . ?
O1 C12 C14 106.9(3) . . ?
O1 C12 H12A 110.4 . . ?
C14 C12 H12A 110.4 . . ?
O1 C12 H12B 110.4 . . ?
C14 C12 H12B 110.4 . . ?
H12A C12 H12B 108.6 . . ?
C14 C13 Cl3 127.5(3) . . ?
C14 C13 S1 113.7(3) . . ?
Cl3 C13 S1 118.8(2) . . ?
C13 C14 C15 110.0(3) . . ?
C13 C14 C12 126.4(3) . . ?
C15 C14 C12 123.6(3) . . ?
C16 C15 C14 114.2(4) . . ?
C16 C15 H15 122.9 . . ?
C14 C15 H15 122.9 . . ?
C15 C16 S1 111.6(3) . . ?
C15 C16 H16 124.2 . . ?
S1 C16 H16 124.2 . . ?
C9 N1 C11 108.6(3) . . ?
C9 N1 C8 123.6(3) . . ?
C11 N1 C8 127.4(3) . . ?
C9 N2 C10 109.1(3) . . ?
C9 N2 H2N 122(3) . . ?
C10 N2 H2N 129(3) . . ?
C7 O1 C12 114.0(2) . . ?
Cl1B Cl1A C2 81.3(5) . . ?
Cl1A Cl1B C2 72.5(5) . . ?
C16 S1 C13 90.4(2) . . ?

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
C6 C1 C2 C3 -1.1(6) . . . . ?
C7 C1 C2 C3 -179.5(4) . . . . ?
C6 C1 C2 Cl1A 161.7(7) . . . . ?
C7 C1 C2 Cl1A -16.7(8) . . . . ?
C6 C1 C2 Cl1B -168.7(7) . . . . ?
C7 C1 C2 Cl1B 12.9(8) . . . . ?
C1 C2 C3 C4 -0.2(6) . . . . ?
Cl1A C2 C3 C4 -162.7(8) . . . . ?
Cl1B C2 C3 C4 167.9(7) . . . . ?
C2 C3 C4 C5 1.6(7) . . . . ?
C2 C3 C4 Cl2 179.9(3) . . . . ?
C3 C4 C5 C6 -1.7(8) . . . . ?
Cl2 C4 C5 C6 -180.0(5) . . . . ?
C2 C1 C6 C5 1.0(8) . . . . ?
C7 C1 C6 C5 179.5(5) . . . . ?
C4 C5 C6 C1 0.4(9) . . . . ?
C6 C1 C7 O1 45.6(5) . . . . ?
C2 C1 C7 O1 -136.1(3) . . . . ?
C6 C1 C7 C8 -71.8(5) . . . . ?
C2 C1 C7 C8 106.6(4) . . . . ?
O1 C7 C8 N1 52.6(4) . . . . ?
C1 C7 C8 N1 173.9(3) . . . . ?
N2 C10 C11 N1 0.3(4) . . . . ?
Cl3 C13 C14 C15 -177.1(3) . . . . ?
S1 C13 C14 C15 1.4(4) . . . . ?
Cl3 C13 C14 C12 2.9(6) . . . . ?
S1 C13 C14 C12 -178.6(3) . . . . ?
O1 C12 C14 C13 126.7(4) . . . . ?
O1 C12 C14 C15 -53.3(5) . . . . ?
C13 C14 C15 C16 -1.8(5) . . . . ?
C12 C14 C15 C16 178.2(4) . . . . ?
C14 C15 C16 S1 1.4(5) . . . . ?
N2 C9 N1 C11 0.7(4) . . . . ?
N2 C9 N1 C8 174.0(3) . . . . ?
C10 C11 N1 C9 -0.6(4) . . . . ?
C10 C11 N1 C8 -173.6(3) . . . . ?
C7 C8 N1 C9 -96.7(4) . . . . ?
C7 C8 N1 C11 75.3(4) . . . . ?
N1 C9 N2 C10 -0.5(4) . . . . ?
C11 C10 N2 C9 0.1(5) . . . . ?
C1 C7 O1 C12 84.2(3) . . . . ?
C8 C7 O1 C12 -156.3(3) . . . . ?
C14 C12 O1 C7 157.4(3) . . . . ?
C1 C2 Cl1A Cl1B 104.8(9) . . . . ?
C3 C2 Cl1A Cl1B -91.6(6) . . . . ?
C1 C2 Cl1B Cl1A -89.6(10) . . . . ?
C3 C2 Cl1B Cl1A 102.1(6) . . . . ?
C15 C16 S1 C13 -0.5(3) . . . . ?
C14 C13 S1 C16 -0.6(3) . . . . ?
Cl3 C13 S1 C16 178.1(2) . . . . ?

_refine_diff_density_max         0.625
_refine_diff_density_min         -0.393
_refine_diff_density_rms         0.072

####################################################################### 
# 
# 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_TCZ-CNBA
_database_code_depnum_ccdc_archive 'CCDC 2285608'
loop_
_audit_author_name
_audit_author_address
'Tejender Thakur'
;CSIR Central Drug Research Institute
India
;
_audit_update_record             
;
2023-07-31 deposited with the CCDC.	2023-11-14 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT029_TCZ-CNBA            
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.861 Why?
RESPONSE: poor crystal quality, crystal exhibit twining and the major component is used for structure solution
;
_vrf_PLAT911_TCZ-CNBA            
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600        620 Report
RESPONSE: poor crystal quality, crystal exhibit twining and the major component is used for structure solution
;
# Added during the CSD deposition process: Monday 31 July 2023 10:31 AM
# end Validation Reply Form


_audit_creation_method           SHELXL-2019/2
_shelx_SHELXL_version_number     2019/2
_chemical_name_systematic        ?
_chemical_name_common            
'Tiaconazole-2-Chloro-4-nitrobenzoic acid cocrystal'
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H13 Cl3 N2 O S, C7 H3 Cl N O4'
_chemical_formula_sum            'C23 H16 Cl4 N3 O5 S'
_chemical_formula_weight         588.25

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'
Cl Cl 0.1484 0.1585 '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                   7.7627(5)
_cell_length_b                   11.9414(6)
_cell_length_c                   14.9934(7)
_cell_angle_alpha                110.029(5)
_cell_angle_beta                 96.939(5)
_cell_angle_gamma                103.891(5)
_cell_volume                     1235.79(13)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3939
_cell_measurement_theta_min      2.8410
_cell_measurement_theta_max      30.4050

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.581
_exptl_crystal_F_000             598
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.270
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.090
_exptl_absorpt_coefficient_mu    0.605
_shelx_estimated_absorpt_T_min   0.854
_shelx_estimated_absorpt_T_max   0.948
_exptl_absorpt_correction_T_min  0.33594
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.504
_oxdiff_exptl_absorpt_empirical_full_max 2.303
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   MicroMax003_Mo
_diffrn_radiation_monochromator  Confocal
_diffrn_measurement_specimen_support Loop
_diffrn_detector                 CCD
_diffrn_measurement_device       
;
AFC12 (Right): Kappa 3 circle
;
_diffrn_measurement_device_type  
;
Rigaku Saturn724+ (4x4 bin mode)
;
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_reflns_number            12445
_diffrn_reflns_av_unetI/netI     0.1240
_diffrn_reflns_av_R_equivalents  0.1408
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.483
_diffrn_reflns_theta_max         31.400
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.731
_diffrn_measured_fraction_theta_full 0.861
_diffrn_reflns_Laue_measured_fraction_max 0.731
_diffrn_reflns_Laue_measured_fraction_full 0.861
_diffrn_reflns_point_group_measured_fraction_max 0.731
_diffrn_reflns_point_group_measured_fraction_full 0.861
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0177153000
_diffrn_orient_matrix_UB_12      -0.0095829000
_diffrn_orient_matrix_UB_13      -0.0500157000
_diffrn_orient_matrix_UB_21      -0.0237310000
_diffrn_orient_matrix_UB_22      -0.0655797000
_diffrn_orient_matrix_UB_23      -0.0128564000
_diffrn_orient_matrix_UB_31      -0.0918952000
_diffrn_orient_matrix_UB_32      -0.0022438000
_diffrn_orient_matrix_UB_33      0.0008814000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -30.00  70.00   0.50   10.00    --  -20.00  60.00   0.00  200
  2  ω    -30.00  70.00   0.50   10.00    --  -20.00  60.00  90.00  200
  3  ω   -110.00 -10.00   0.50   10.00    --  -20.00 -60.00 180.00  200
  4  ω   -110.00 -10.00   0.50   10.00    --  -20.00 -60.00 180.00  200
;
_oxdiff_twin_items               2
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
_oxdiff_twin_reflns_isolated
_oxdiff_twin_reflns_overlapped
_twin_individual_twin_lattice_type
_twin_individual_twin_matrix_11
_twin_individual_twin_matrix_12
_twin_individual_twin_matrix_13
_twin_individual_twin_matrix_21
_twin_individual_twin_matrix_22
_twin_individual_twin_matrix_23
_twin_individual_twin_matrix_31
_twin_individual_twin_matrix_32
_twin_individual_twin_matrix_33
1 0.6368 9774 3560 ref 1.0000 0.0000 0.0000 0.0000 1.0000 0.0000 0.0000 0.0000
1.0000
2 0.3632 9496 3560 nmt 1.0088 0.0184 0.0121 0.0207 1.0532 0.1556 -0.1251
-0.2611 0.9014
_oxdiff_twin_integration_method  simultaneous
_twin_special_details            
;
Component 2 rotated by 10.7356° 
around [-0.90 0.44 -0.03] (reciprocal) or [-1.00 0.02 -0.07] (direct)
;
_reflns_number_total             5965
_reflns_number_gt                3665
_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       'CrystalClear-SM Expert 2.1 b28 (Rigaku, 2013)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'
_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)+(0.1343P)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         5965
_refine_ls_number_parameters     334
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1344
_refine_ls_R_factor_gt           0.0874
_refine_ls_wR_factor_ref         0.2393
_refine_ls_wR_factor_gt          0.2182
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.047
_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
C1 C 0.8244(6) 0.6135(4) 0.7833(3) 0.0198(10) Uani 1 1 d . . . . .
C2 C 0.8871(6) 0.5795(5) 0.8588(3) 0.0221(10) Uani 1 1 d . . . . .
C3 C 0.9096(6) 0.6548(5) 0.9561(3) 0.0277(12) Uani 1 1 d . . . . .
H3 H 0.948954 0.628395 1.005945 0.033 Uiso 1 1 calc R U . . .
C4 C 0.8746(7) 0.7670(5) 0.9796(3) 0.0317(13) Uani 1 1 d . . . . .
C5 C 0.8134(7) 0.8063(5) 0.9066(4) 0.0304(12) Uani 1 1 d . . . . .
H5 H 0.789269 0.884325 0.922994 0.036 Uiso 1 1 calc R U . . .
C6 C 0.7891(7) 0.7279(5) 0.8095(3) 0.0252(11) Uani 1 1 d . . . . .
H6 H 0.747030 0.753454 0.759684 0.030 Uiso 1 1 calc R U . . .
C7 C 0.7971(6) 0.5298(4) 0.6775(3) 0.0195(10) Uani 1 1 d . . . . .
H7 H 0.903220 0.496836 0.668162 0.023 Uiso 1 1 calc R U . . .
C8 C 0.6210(6) 0.4205(4) 0.6460(3) 0.0214(10) Uani 1 1 d . . . . .
H8A H 0.610619 0.388230 0.698392 0.026 Uiso 1 1 calc R U . . .
H8B H 0.515040 0.450778 0.635854 0.026 Uiso 1 1 calc R U . . .
C9 C 0.5947(7) 0.3187(4) 0.4654(3) 0.0241(11) Uani 1 1 d . . . . .
H9 H 0.573607 0.385283 0.449238 0.029 Uiso 1 1 calc R U . . .
C10 C 0.6362(7) 0.1411(5) 0.4532(3) 0.0242(11) Uani 1 1 d . . . . .
H10 H 0.648773 0.059795 0.425976 0.029 Uiso 1 1 calc R U . . .
C11 C 0.6459(7) 0.2059(4) 0.5491(3) 0.0225(10) Uani 1 1 d . . . . .
H11 H 0.667544 0.179257 0.601129 0.027 Uiso 1 1 calc R U . . .
C12 C 0.9428(7) 0.6698(5) 0.6077(4) 0.0244(10) Uani 1 1 d . . . . .
H12A H 1.027010 0.619868 0.588769 0.029 Uiso 1 1 calc R U . . .
H12B H 1.001525 0.738749 0.671779 0.029 Uiso 1 1 calc R U . . .
C13 C 0.8779(6) 0.8359(4) 0.5497(3) 0.0203(10) Uani 1 1 d . . . . .
C14 C 0.8960(6) 0.7212(4) 0.5319(3) 0.0197(10) Uani 1 1 d . . . . .
C15 C 0.8687(6) 0.6518(4) 0.4297(3) 0.0243(11) Uani 1 1 d . . . . .
H15 H 0.873950 0.568551 0.402617 0.029 Uiso 1 1 calc R U . . .
C16 C 0.8346(7) 0.7182(5) 0.3760(3) 0.0265(12) Uani 1 1 d . . . . .
H16 H 0.816483 0.687308 0.307097 0.032 Uiso 1 1 calc R U . . .
C17 C 0.6428(6) 0.2542(4) 0.1046(3) 0.0158(9) Uani 1 1 d . . . . .
C18 C 0.6078(6) 0.3427(4) 0.0688(3) 0.0186(9) Uani 1 1 d . . . . .
C19 C 0.5825(6) 0.3190(4) -0.0305(3) 0.0218(10) Uani 1 1 d . . . . .
H19 H 0.554333 0.377530 -0.055130 0.026 Uiso 1 1 calc R U . . .
C20 C 0.6000(6) 0.2071(4) -0.0921(3) 0.0188(10) Uani 1 1 d . . . . .
C21 C 0.6397(6) 0.1202(4) -0.0592(3) 0.0204(10) Uani 1 1 d . . . . .
H21 H 0.653537 0.045353 -0.103062 0.024 Uiso 1 1 calc R U . . .
C22 C 0.6592(7) 0.1436(4) 0.0389(3) 0.0207(10) Uani 1 1 d . . . . .
C23 C 0.6556(6) 0.2712(4) 0.2107(3) 0.0201(10) Uani 1 1 d . . . . .
N1 N 0.6179(5) 0.3186(3) 0.5555(2) 0.0192(9) Uani 1 1 d . . . . .
N2 N 0.6053(5) 0.2134(4) 0.4027(3) 0.0219(9) Uani 1 1 d . . . . .
N3 N 0.5680(6) 0.1818(4) -0.1966(3) 0.0230(9) Uani 1 1 d . . . . .
O1 O 0.7714(4) 0.5915(3) 0.6125(2) 0.0203(7) Uani 1 1 d . . . . .
O2 O 0.5871(5) 0.1695(3) 0.2222(2) 0.0266(8) Uani 1 1 d . . . . .
O3 O 0.7239(5) 0.3753(3) 0.2760(2) 0.0304(9) Uani 1 1 d . . . . .
O4 O 0.4858(5) 0.2431(3) -0.2266(2) 0.0283(8) Uani 1 1 d . . . . .
O5 O 0.6207(6) 0.0997(3) -0.2497(2) 0.0358(9) Uani 1 1 d . . . . .
S1 S 0.82782(18) 0.86329(11) 0.44566(8) 0.0266(3) Uani 1 1 d . . . . .
Cl1 Cl 0.93496(17) 0.43735(12) 0.83028(8) 0.0279(3) Uani 1 1 d . . . . .
Cl2 Cl 0.9022(2) 0.86211(15) 1.10068(9) 0.0475(5) Uani 1 1 d . . . . .
Cl3 Cl 0.8921(2) 0.94865(11) 0.66136(8) 0.0358(4) Uani 1 1 d . . . . .
Cl4A Cl 0.58285(16) 0.48264(10) 0.14238(7) 0.0192(3) Uani 0.938(4) 1 d . . P .
.
Cl4B Cl 0.736(5) 0.070(3) 0.080(2) 0.064(9) Uiso 0.062(4) 1 d . . P . .
H2 H 0.605(12) 0.184(8) 0.307(7) 0.11(3) 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
C1 C6 1.390(7) . ?
C1 C2 1.400(6) . ?
C1 C7 1.513(6) . ?
C2 C3 1.390(6) . ?
C2 Cl1 1.746(5) . ?
C3 C4 1.367(8) . ?
C3 H3 0.9500 . ?
C4 C5 1.406(8) . ?
C4 Cl2 1.734(5) . ?
C5 C6 1.396(7) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 O1 1.431(5) . ?
C7 C8 1.536(6) . ?
C7 H7 1.0000 . ?
C8 N1 1.473(6) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 N2 1.316(6) . ?
C9 N1 1.341(5) . ?
C9 H9 0.9500 . ?
C10 C11 1.362(6) . ?
C10 N2 1.370(6) . ?
C10 H10 0.9500 . ?
C11 N1 1.387(6) . ?
C11 H11 0.9500 . ?
C12 O1 1.456(5) . ?
C12 C14 1.512(6) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.349(7) . ?
C13 S1 1.719(5) . ?
C13 Cl3 1.723(4) . ?
C14 C15 1.431(6) . ?
C15 C16 1.353(7) . ?
C15 H15 0.9500 . ?
C16 S1 1.707(5) . ?
C16 H16 0.9500 . ?
C17 C22 1.397(6) . ?
C17 C18 1.403(6) . ?
C17 C23 1.520(5) . ?
C18 C19 1.397(6) . ?
C18 Cl4A 1.730(5) . ?
C19 C20 1.389(7) . ?
C19 H19 0.9500 . ?
C20 C21 1.372(7) . ?
C20 N3 1.468(5) . ?
C21 C22 1.382(6) . ?
C21 H21 0.9500 . ?
C22 Cl4B 1.42(4) . ?
C23 O3 1.229(5) . ?
C23 O2 1.282(5) . ?
N2 H2 1.36(9) . ?
N3 O5 1.223(5) . ?
N3 O4 1.236(5) . ?
O2 H2 1.21(9) . ?

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
C6 C1 C2 117.2(4) . . ?
C6 C1 C7 121.3(4) . . ?
C2 C1 C7 121.5(5) . . ?
C3 C2 C1 121.9(5) . . ?
C3 C2 Cl1 118.8(4) . . ?
C1 C2 Cl1 119.2(4) . . ?
C4 C3 C2 119.5(5) . . ?
C4 C3 H3 120.3 . . ?
C2 C3 H3 120.3 . . ?
C3 C4 C5 120.9(4) . . ?
C3 C4 Cl2 120.1(4) . . ?
C5 C4 Cl2 119.0(5) . . ?
C6 C5 C4 118.4(5) . . ?
C6 C5 H5 120.8 . . ?
C4 C5 H5 120.8 . . ?
C1 C6 C5 122.1(5) . . ?
C1 C6 H6 118.9 . . ?
C5 C6 H6 118.9 . . ?
O1 C7 C1 112.9(4) . . ?
O1 C7 C8 104.2(4) . . ?
C1 C7 C8 110.3(3) . . ?
O1 C7 H7 109.8 . . ?
C1 C7 H7 109.8 . . ?
C8 C7 H7 109.8 . . ?
N1 C8 C7 111.4(4) . . ?
N1 C8 H8A 109.3 . . ?
C7 C8 H8A 109.3 . . ?
N1 C8 H8B 109.3 . . ?
C7 C8 H8B 109.3 . . ?
H8A C8 H8B 108.0 . . ?
N2 C9 N1 110.2(4) . . ?
N2 C9 H9 124.9 . . ?
N1 C9 H9 124.9 . . ?
C11 C10 N2 108.3(4) . . ?
C11 C10 H10 125.9 . . ?
N2 C10 H10 125.9 . . ?
C10 C11 N1 106.2(4) . . ?
C10 C11 H11 126.9 . . ?
N1 C11 H11 126.9 . . ?
O1 C12 C14 106.2(4) . . ?
O1 C12 H12A 110.5 . . ?
C14 C12 H12A 110.5 . . ?
O1 C12 H12B 110.5 . . ?
C14 C12 H12B 110.5 . . ?
H12A C12 H12B 108.7 . . ?
C14 C13 S1 113.2(3) . . ?
C14 C13 Cl3 127.0(4) . . ?
S1 C13 Cl3 119.7(3) . . ?
C13 C14 C15 111.1(4) . . ?
C13 C14 C12 126.0(4) . . ?
C15 C14 C12 122.8(4) . . ?
C16 C15 C14 112.5(4) . . ?
C16 C15 H15 123.8 . . ?
C14 C15 H15 123.8 . . ?
C15 C16 S1 112.6(3) . . ?
C15 C16 H16 123.7 . . ?
S1 C16 H16 123.7 . . ?
C22 C17 C18 118.3(4) . . ?
C22 C17 C23 118.8(4) . . ?
C18 C17 C23 122.9(4) . . ?
C19 C18 C17 121.1(4) . . ?
C19 C18 Cl4A 116.0(4) . . ?
C17 C18 Cl4A 122.9(3) . . ?
C20 C19 C18 117.7(4) . . ?
C20 C19 H19 121.1 . . ?
C18 C19 H19 121.1 . . ?
C21 C20 C19 122.8(4) . . ?
C21 C20 N3 120.0(4) . . ?
C19 C20 N3 117.2(4) . . ?
C20 C21 C22 118.7(4) . . ?
C20 C21 H21 120.7 . . ?
C22 C21 H21 120.7 . . ?
C21 C22 C17 121.4(4) . . ?
C21 C22 Cl4B 120.6(13) . . ?
C17 C22 Cl4B 116.6(13) . . ?
O3 C23 O2 125.9(4) . . ?
O3 C23 C17 120.5(4) . . ?
O2 C23 C17 113.7(4) . . ?
C9 N1 C11 107.5(4) . . ?
C9 N1 C8 126.9(4) . . ?
C11 N1 C8 125.6(4) . . ?
C9 N2 C10 107.8(4) . . ?
C9 N2 H2 127(4) . . ?
C10 N2 H2 125(4) . . ?
O5 N3 O4 123.4(4) . . ?
O5 N3 C20 118.5(4) . . ?
O4 N3 C20 118.0(4) . . ?
C7 O1 C12 112.2(3) . . ?
C23 O2 H2 113(4) . . ?
C16 S1 C13 90.5(2) . . ?

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
C6 C1 C2 C3 1.4(7) . . . . ?
C7 C1 C2 C3 -178.8(4) . . . . ?
C6 C1 C2 Cl1 -179.6(3) . . . . ?
C7 C1 C2 Cl1 0.1(6) . . . . ?
C1 C2 C3 C4 -1.8(7) . . . . ?
Cl1 C2 C3 C4 179.3(4) . . . . ?
C2 C3 C4 C5 1.0(8) . . . . ?
C2 C3 C4 Cl2 -179.9(4) . . . . ?
C3 C4 C5 C6 0.1(8) . . . . ?
Cl2 C4 C5 C6 -179.0(4) . . . . ?
C2 C1 C6 C5 -0.3(7) . . . . ?
C7 C1 C6 C5 180.0(4) . . . . ?
C4 C5 C6 C1 -0.4(8) . . . . ?
C6 C1 C7 O1 12.6(6) . . . . ?
C2 C1 C7 O1 -167.2(4) . . . . ?
C6 C1 C7 C8 -103.5(5) . . . . ?
C2 C1 C7 C8 76.8(6) . . . . ?
O1 C7 C8 N1 75.8(5) . . . . ?
C1 C7 C8 N1 -162.7(4) . . . . ?
N2 C10 C11 N1 0.7(5) . . . . ?
S1 C13 C14 C15 0.1(5) . . . . ?
Cl3 C13 C14 C15 177.8(3) . . . . ?
S1 C13 C14 C12 178.9(4) . . . . ?
Cl3 C13 C14 C12 -3.5(8) . . . . ?
O1 C12 C14 C13 99.4(5) . . . . ?
O1 C12 C14 C15 -82.0(6) . . . . ?
C13 C14 C15 C16 1.0(6) . . . . ?
C12 C14 C15 C16 -177.8(4) . . . . ?
C14 C15 C16 S1 -1.7(5) . . . . ?
C22 C17 C18 C19 2.6(7) . . . . ?
C23 C17 C18 C19 -174.8(4) . . . . ?
C22 C17 C18 Cl4A 179.5(3) . . . . ?
C23 C17 C18 Cl4A 2.2(6) . . . . ?
C17 C18 C19 C20 -2.4(7) . . . . ?
Cl4A C18 C19 C20 -179.5(3) . . . . ?
C18 C19 C20 C21 0.3(7) . . . . ?
C18 C19 C20 N3 178.3(4) . . . . ?
C19 C20 C21 C22 1.5(7) . . . . ?
N3 C20 C21 C22 -176.5(4) . . . . ?
C20 C21 C22 C17 -1.3(7) . . . . ?
C20 C21 C22 Cl4B -167.1(15) . . . . ?
C18 C17 C22 C21 -0.7(7) . . . . ?
C23 C17 C22 C21 176.7(4) . . . . ?
C18 C17 C22 Cl4B 165.7(15) . . . . ?
C23 C17 C22 Cl4B -16.9(15) . . . . ?
C22 C17 C23 O3 146.4(5) . . . . ?
C18 C17 C23 O3 -36.3(7) . . . . ?
C22 C17 C23 O2 -34.8(6) . . . . ?
C18 C17 C23 O2 142.5(5) . . . . ?
N2 C9 N1 C11 0.3(6) . . . . ?
N2 C9 N1 C8 178.1(4) . . . . ?
C10 C11 N1 C9 -0.6(5) . . . . ?
C10 C11 N1 C8 -178.4(4) . . . . ?
C7 C8 N1 C9 -72.5(6) . . . . ?
C7 C8 N1 C11 104.9(5) . . . . ?
N1 C9 N2 C10 0.1(6) . . . . ?
C11 C10 N2 C9 -0.5(6) . . . . ?
C21 C20 N3 O5 -18.0(6) . . . . ?
C19 C20 N3 O5 163.9(4) . . . . ?
C21 C20 N3 O4 160.6(4) . . . . ?
C19 C20 N3 O4 -17.4(6) . . . . ?
C1 C7 O1 C12 80.0(5) . . . . ?
C8 C7 O1 C12 -160.3(4) . . . . ?
C14 C12 O1 C7 176.2(4) . . . . ?
C15 C16 S1 C13 1.5(4) . . . . ?
C14 C13 S1 C16 -0.9(4) . . . . ?
Cl3 C13 S1 C16 -178.8(3) . . . . ?

_refine_diff_density_max         0.593
_refine_diff_density_min         -0.883
_refine_diff_density_rms         0.145

####################################################################### 
# 
# 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_TCZ-FUMH2
_database_code_depnum_ccdc_archive 'CCDC 2285610'
loop_
_audit_author_name
_audit_author_address
'Tejender Thakur'
;CSIR Central Drug Research Institute
India
;
_audit_update_record             
;
2023-07-31 deposited with the CCDC.	2023-11-14 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT353_TCZ-FUMH2           
;
PROBLEM: Long   N-H (N0.87,N1.01A)  N2       - H2N      .       1.16 Ang.
RESPONSE: Elongated N-H distance indicate partial proton tranfer between the fumaric acid and tioconazole drug
;
# Added during the CSD deposition process: Monday 31 July 2023 10:31 AM
# end Validation Reply Form


_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            'Tioconazole-fumerate salt hemihydrate'
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C16  H14  N2  O  S  Cl3),2(C4 H3 O4), H2 O'
_chemical_formula_sum            'C40 H36 Cl6 N4 O11 S2'
_chemical_formula_weight         1025.55

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'
Cl Cl 0.1484 0.1585 '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                   7.8551(5)
_cell_length_b                   46.374(2)
_cell_length_c                   12.4658(5)
_cell_angle_alpha                90
_cell_angle_beta                 90.468(4)
_cell_angle_gamma                90
_cell_volume                     4540.8(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    9230
_cell_measurement_theta_min      2.6400
_cell_measurement_theta_max      30.3370

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.500
_exptl_crystal_F_000             2104
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.290
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.533
_shelx_estimated_absorpt_T_min   0.861
_shelx_estimated_absorpt_T_max   0.974
_exptl_absorpt_correction_T_min  0.16908
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   MicroMax003_Mo
_diffrn_radiation_monochromator  Confocal
_diffrn_measurement_specimen_support Loop
_diffrn_detector                 CCD
_diffrn_measurement_device       
;
AFC12 (Right): Kappa 3 circle
;
_diffrn_measurement_device_type  
;
Rigaku Saturn724+ (4x4 bin mode)
;
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_reflns_number            48432
_diffrn_reflns_av_unetI/netI     0.1354
_diffrn_reflns_av_R_equivalents  0.1486
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -49
_diffrn_reflns_limit_k_max       67
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.757
_diffrn_reflns_theta_max         31.498
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.882
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.882
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.882
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             13357
_reflns_number_gt                5446
_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       'CrystalClear-SM Expert 2.1 b28 (Rigaku, 2013)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_structure_solution    'SHELXS-2013/1(Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'
_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)+(0.1126P)²+2.7069P] 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     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.0049(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         13357
_refine_ls_number_parameters     590
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.2218
_refine_ls_R_factor_gt           0.1029
_refine_ls_wR_factor_ref         0.3075
_refine_ls_wR_factor_gt          0.2385
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_restrained_S_all      1.034
_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
C1 C 0.8393(6) 0.09451(11) 0.6601(3) 0.0457(12) Uani 1 1 d . . . . .
C2 C 0.7606(6) 0.09672(12) 0.7613(4) 0.0477(12) Uani 1 1 d . . . . .
C3 C 0.7699(7) 0.07435(12) 0.8349(4) 0.0542(13) Uani 1 1 d . . . . .
H3 H 0.716828 0.075904 0.901066 0.065 Uiso 1 1 calc R U . . .
C4 C 0.8583(7) 0.05000(13) 0.8087(4) 0.0569(14) Uani 1 1 d . . . . .
C5 C 0.9388(7) 0.04690(12) 0.7102(4) 0.0558(14) Uani 1 1 d . . . . .
H5 H 0.997735 0.030140 0.693167 0.067 Uiso 1 1 calc R U . . .
C6 C 0.9280(6) 0.06938(12) 0.6392(4) 0.0502(13) Uani 1 1 d . . . . .
H6 H 0.983118 0.067668 0.573738 0.060 Uiso 1 1 calc R U . . .
C7 C 0.8199(6) 0.11871(11) 0.5780(3) 0.0454(11) Uani 1 1 d . . . . .
H7 H 0.701245 0.125232 0.576512 0.054 Uiso 1 1 calc R U . . .
C8 C 0.9352(7) 0.14425(11) 0.5995(3) 0.0493(12) Uani 1 1 d . . . . .
H8A H 0.928815 0.149466 0.674738 0.059 Uiso 1 1 calc R U . . .
H8B H 1.051912 0.138933 0.584279 0.059 Uiso 1 1 calc R U . . .
C9 C 0.9089(8) 0.17162(14) 0.4278(4) 0.0638(16) Uani 1 1 d . . . . .
H9 H 0.967471 0.158627 0.384827 0.077 Uiso 1 1 calc R U . . .
C10 C 0.7584(7) 0.20825(13) 0.4776(4) 0.0626(15) Uani 1 1 d . . . . .
H10 H 0.695256 0.225200 0.475011 0.075 Uiso 1 1 calc R U . . .
C11 C 0.7900(7) 0.19209(13) 0.5660(4) 0.0609(15) Uani 1 1 d . . . . .
H11 H 0.753164 0.195894 0.635303 0.073 Uiso 1 1 calc R U . . .
C12 C 0.7305(6) 0.09345(12) 0.4197(4) 0.0524(13) Uani 1 1 d . . . . .
H12A H 0.637248 0.106581 0.404551 0.063 Uiso 1 1 calc R U . . .
H12B H 0.688505 0.078234 0.465861 0.063 Uiso 1 1 calc R U . . .
C13 C 0.8276(7) 0.05272(13) 0.3003(4) 0.0564(14) Uani 1 1 d . . . . .
C14 C 0.7937(6) 0.08075(12) 0.3173(4) 0.0456(12) Uani 1 1 d . . . . .
C15 C 0.8218(6) 0.09703(13) 0.2221(4) 0.0541(13) Uani 1 1 d . . . . .
H15 H 0.806099 0.116870 0.217450 0.065 Uiso 1 1 calc R U . . .
C16 C 0.8736(7) 0.08055(16) 0.1395(4) 0.0716(19) Uani 1 1 d . . . . .
H16 H 0.897504 0.087811 0.071732 0.086 Uiso 1 1 calc R U . . .
C17 C 0.3353(6) 0.09526(11) 0.0781(3) 0.0434(11) Uani 1 1 d . . . . .
C18 C 0.2580(6) 0.09728(11) -0.0242(3) 0.0424(11) Uani 1 1 d . . . . .
C19 C 0.2697(7) 0.07542(12) -0.0985(4) 0.0501(13) Uani 1 1 d . . . . .
H19 H 0.216858 0.077190 -0.165168 0.060 Uiso 1 1 calc R U . . .
C20 C 0.3597(7) 0.05107(13) -0.0733(4) 0.0546(13) Uani 1 1 d . . . . .
C21 C 0.4376(7) 0.04784(12) 0.0262(4) 0.0546(13) Uani 1 1 d . . . . .
H21 H 0.496343 0.031025 0.043452 0.065 Uiso 1 1 calc R U . . .
C22 C 0.4260(6) 0.07016(12) 0.0992(4) 0.0489(12) Uani 1 1 d . . . . .
H22 H 0.481185 0.068307 0.165108 0.059 Uiso 1 1 calc R U . . .
C23 C 0.3159(6) 0.11906(11) 0.1614(3) 0.0434(11) Uani 1 1 d . . . . .
H23 H 0.197501 0.125698 0.162449 0.052 Uiso 1 1 calc R U . . .
C24 C 0.4334(7) 0.14446(11) 0.1398(3) 0.0487(12) Uani 1 1 d . . . . .
H24A H 0.550149 0.139036 0.155868 0.058 Uiso 1 1 calc R U . . .
H24B H 0.426303 0.149745 0.064635 0.058 Uiso 1 1 calc R U . . .
C25 C 0.4038(8) 0.17121(13) 0.3121(4) 0.0625(15) Uani 1 1 d . . . . .
H25 H 0.460828 0.157845 0.354841 0.075 Uiso 1 1 calc R U . . .
C26 C 0.2602(8) 0.20867(14) 0.2620(4) 0.0686(17) Uani 1 1 d . . . . .
H26 H 0.200980 0.226029 0.263531 0.082 Uiso 1 1 calc R U . . .
C27 C 0.2924(8) 0.19258(13) 0.1744(4) 0.0619(15) Uani 1 1 d . . . . .
H27 H 0.257812 0.196706 0.104560 0.074 Uiso 1 1 calc R U . . .
C28 C 0.2299(6) 0.09275(12) 0.3174(3) 0.0496(13) Uani 1 1 d . . . . .
H28A H 0.185533 0.078186 0.268866 0.060 Uiso 1 1 calc R U . . .
H28B H 0.137864 0.105798 0.335191 0.060 Uiso 1 1 calc R U . . .
C29 C 0.3289(7) 0.05046(12) 0.4295(4) 0.0529(13) Uani 1 1 d . . . . .
C30 C 0.2959(6) 0.07868(12) 0.4173(3) 0.0460(12) Uani 1 1 d . . . . .
C31 C 0.3275(6) 0.09405(14) 0.5158(4) 0.0574(14) Uani 1 1 d . . . . .
H31 H 0.312049 0.113810 0.524022 0.069 Uiso 1 1 calc R U . . .
C32 C 0.3824(7) 0.07629(15) 0.5951(4) 0.0683(18) Uani 1 1 d . . . . .
H32 H 0.409706 0.082582 0.663982 0.082 Uiso 1 1 calc R U . . .
C33 C 0.3562(8) 0.18555(14) 0.6033(4) 0.0607(15) Uani 1 1 d . . . . .
C34 C 0.3825(7) 0.18877(13) 0.7219(4) 0.0573(14) Uani 1 1 d . . . . .
H34 H 0.358001 0.173094 0.765644 0.069 Uiso 1 1 calc R U . . .
C35 C 0.4387(7) 0.21270(13) 0.7676(4) 0.0559(14) Uani 1 1 d . . . . .
H35 H 0.457523 0.228928 0.725529 0.067 Uiso 1 1 calc R U . . .
C36 C 0.4720(7) 0.21420(13) 0.8834(4) 0.0529(13) Uani 1 1 d . . . . .
C37 C 0.3602(8) 0.31357(14) 0.6373(4) 0.0611(15) Uani 1 1 d . . . . .
C38 C 0.3838(7) 0.31031(12) 0.5192(4) 0.0567(14) Uani 1 1 d . . . . .
H38 H 0.357265 0.325977 0.475547 0.068 Uiso 1 1 calc R U . . .
C39 C 0.4395(7) 0.28679(12) 0.4731(4) 0.0555(14) Uani 1 1 d . . . . .
H39 H 0.458856 0.270521 0.515072 0.067 Uiso 1 1 calc R U . . .
C40 C 0.4729(7) 0.28516(13) 0.3562(4) 0.0564(14) Uani 1 1 d . . . . .
N1 N 0.8871(5) 0.16894(9) 0.5340(3) 0.0477(10) Uani 1 1 d . . . . .
N2 N 0.8353(6) 0.19524(11) 0.3937(3) 0.0623(13) Uani 1 1 d . . . . .
N3 N 0.3846(5) 0.16917(9) 0.2065(3) 0.0471(10) Uani 1 1 d . . . . .
N4 N 0.3304(6) 0.19485(11) 0.3477(3) 0.0631(13) Uani 1 1 d . . . . .
O1 O 0.8659(4) 0.10866(8) 0.4730(2) 0.0475(8) Uani 1 1 d . . . . .
O2 O 0.3638(4) 0.10843(7) 0.2662(2) 0.0456(8) Uani 1 1 d . . . . .
O3 O 0.3713(7) 0.16141(10) 0.5643(3) 0.0885(15) Uani 1 1 d . . . . .
O4 O 0.3234(5) 0.20844(9) 0.5509(3) 0.0687(11) Uani 1 1 d . . . . .
O5 O 0.4546(7) 0.19483(10) 0.9457(3) 0.0900(15) Uani 1 1 d . . . . .
O6 O 0.5286(6) 0.23991(9) 0.9131(3) 0.0697(12) Uani 1 1 d . . . . .
H6O H 0.567293 0.238978 0.974273 0.104 Uiso 1 1 calc R U . . .
O7 O 0.3788(8) 0.33724(10) 0.6768(4) 0.1009(17) Uani 1 1 d . . . . .
O8 O 0.3280(6) 0.29050(9) 0.6903(3) 0.0711(12) Uani 1 1 d . . . . .
O9 O 0.4509(7) 0.30498(11) 0.2966(3) 0.0929(16) Uani 1 1 d . . . . .
O10 O 0.5300(6) 0.25959(9) 0.3268(3) 0.0714(12) Uani 1 1 d . . . . .
O11 O 0.1144(6) 0.24974(10) 0.6201(3) 0.0571(10) Uani 1 1 d D . . . .
S1 S 0.8905(2) 0.04508(4) 0.17232(12) 0.0728(5) Uani 1 1 d . . . . .
S2 S 0.3963(2) 0.04140(4) 0.55578(12) 0.0730(5) Uani 1 1 d . . . . .
Cl1 Cl 0.6460(2) 0.12723(3) 0.79641(11) 0.0717(5) Uani 1 1 d . . . . .
Cl2 Cl 0.8684(2) 0.02176(4) 0.90027(12) 0.0818(5) Uani 1 1 d . . . . .
Cl3 Cl 0.8144(3) 0.02518(4) 0.39236(14) 0.0884(6) Uani 1 1 d . . . . .
Cl4 Cl 0.1431(2) 0.12786(4) -0.05919(11) 0.0696(5) Uani 1 1 d . . . . .
Cl5 Cl 0.3743(2) 0.02342(4) -0.16634(11) 0.0773(5) Uani 1 1 d . . . . .
Cl6 Cl 0.3097(3) 0.02387(4) 0.33438(14) 0.0871(6) Uani 1 1 d . . . . .
H2N H 0.815(9) 0.2034(17) 0.307(6) 0.13(3) Uiso 1 1 d . . . . .
H4N H 0.328(11) 0.204(2) 0.429(7) 0.17(4) Uiso 1 1 d . . . . .
H10O H 0.541(11) 0.2605(18) 0.260(7) 0.14(3) Uiso 1 1 d . . . . .
H11A H 0.188(7) 0.2371(12) 0.605(6) 0.10(3) Uiso 1 1 d D . . . .
H11B H 0.199(7) 0.2613(15) 0.626(6) 0.13(4) Uiso 1 1 d 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
C1 C6 1.384(7) . ?
C1 C2 1.413(6) . ?
C1 C7 1.525(7) . ?
C2 C3 1.386(7) . ?
C2 Cl1 1.735(5) . ?
C3 C4 1.367(8) . ?
C3 H3 0.9300 . ?
C4 C5 1.394(7) . ?
C4 Cl2 1.738(5) . ?
C5 C6 1.369(7) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 O1 1.438(5) . ?
C7 C8 1.514(7) . ?
C7 H7 0.9800 . ?
C8 N1 1.454(6) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 N2 1.308(7) . ?
C9 N1 1.343(6) . ?
C9 H9 0.9300 . ?
C10 C11 1.354(8) . ?
C10 N2 1.354(7) . ?
C10 H10 0.9300 . ?
C11 N1 1.378(7) . ?
C11 H11 0.9300 . ?
C12 O1 1.435(6) . ?
C12 C14 1.494(6) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.344(7) . ?
C13 S1 1.711(5) . ?
C13 Cl3 1.721(6) . ?
C14 C15 1.426(7) . ?
C15 C16 1.348(8) . ?
C15 H15 0.9300 . ?
C16 S1 1.700(7) . ?
C16 H16 0.9300 . ?
C17 C22 1.389(7) . ?
C17 C18 1.410(6) . ?
C17 C23 1.524(7) . ?
C18 C19 1.377(6) . ?
C18 Cl4 1.735(5) . ?
C19 C20 1.367(7) . ?
C19 H19 0.9300 . ?
C20 C21 1.387(7) . ?
C20 Cl5 1.734(5) . ?
C21 C22 1.381(7) . ?
C21 H21 0.9300 . ?
C22 H22 0.9300 . ?
C23 O2 1.442(5) . ?
C23 C24 1.522(7) . ?
C23 H23 0.9800 . ?
C24 N3 1.468(6) . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C25 N4 1.317(7) . ?
C25 N3 1.327(6) . ?
C25 H25 0.9300 . ?
C26 C27 1.349(7) . ?
C26 N4 1.359(7) . ?
C26 H26 0.9300 . ?
C27 N3 1.363(7) . ?
C27 H27 0.9300 . ?
C28 O2 1.433(5) . ?
C28 C30 1.494(6) . ?
C28 H28A 0.9700 . ?
C28 H28B 0.9700 . ?
C29 C30 1.343(7) . ?
C29 S2 1.709(5) . ?
C29 Cl6 1.716(6) . ?
C30 C31 1.440(7) . ?
C31 C32 1.355(8) . ?
C31 H31 0.9300 . ?
C32 S2 1.694(7) . ?
C32 H32 0.9300 . ?
C33 O3 1.227(7) . ?
C33 O4 1.272(7) . ?
C33 C34 1.498(7) . ?
C34 C35 1.322(7) . ?
C34 H34 0.9300 . ?
C35 C36 1.467(6) . ?
C35 H35 0.9300 . ?
C36 O5 1.196(6) . ?
C36 O6 1.324(6) . ?
C37 O7 1.212(7) . ?
C37 O8 1.284(7) . ?
C37 C38 1.493(7) . ?
C38 C39 1.310(7) . ?
C38 H38 0.9300 . ?
C39 C40 1.484(6) . ?
C39 H39 0.9300 . ?
C40 O9 1.194(7) . ?
C40 O10 1.320(7) . ?
N2 H2N 1.15(8) . ?
N4 H4N 1.10(9) . ?
O6 H6O 0.8200 . ?
O10 H10O 0.84(8) . ?
O11 H11A 0.85(2) . ?
O11 H11B 0.86(2) . ?

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
C6 C1 C2 117.0(4) . . ?
C6 C1 C7 122.7(4) . . ?
C2 C1 C7 120.3(4) . . ?
C3 C2 C1 121.1(5) . . ?
C3 C2 Cl1 117.9(4) . . ?
C1 C2 Cl1 121.1(4) . . ?
C4 C3 C2 119.0(5) . . ?
C4 C3 H3 120.5 . . ?
C2 C3 H3 120.5 . . ?
C3 C4 C5 122.0(5) . . ?
C3 C4 Cl2 119.1(4) . . ?
C5 C4 Cl2 118.8(5) . . ?
C6 C5 C4 117.7(5) . . ?
C6 C5 H5 121.1 . . ?
C4 C5 H5 121.1 . . ?
C5 C6 C1 123.2(5) . . ?
C5 C6 H6 118.4 . . ?
C1 C6 H6 118.4 . . ?
O1 C7 C8 105.1(4) . . ?
O1 C7 C1 110.3(4) . . ?
C8 C7 C1 113.6(4) . . ?
O1 C7 H7 109.2 . . ?
C8 C7 H7 109.2 . . ?
C1 C7 H7 109.2 . . ?
N1 C8 C7 111.4(4) . . ?
N1 C8 H8A 109.4 . . ?
C7 C8 H8A 109.4 . . ?
N1 C8 H8B 109.4 . . ?
C7 C8 H8B 109.4 . . ?
H8A C8 H8B 108.0 . . ?
N2 C9 N1 109.8(5) . . ?
N2 C9 H9 125.1 . . ?
N1 C9 H9 125.1 . . ?
C11 C10 N2 107.6(5) . . ?
C11 C10 H10 126.2 . . ?
N2 C10 H10 126.2 . . ?
C10 C11 N1 107.1(5) . . ?
C10 C11 H11 126.5 . . ?
N1 C11 H11 126.5 . . ?
O1 C12 C14 109.8(4) . . ?
O1 C12 H12A 109.7 . . ?
C14 C12 H12A 109.7 . . ?
O1 C12 H12B 109.7 . . ?
C14 C12 H12B 109.7 . . ?
H12A C12 H12B 108.2 . . ?
C14 C13 S1 114.0(4) . . ?
C14 C13 Cl3 126.8(4) . . ?
S1 C13 Cl3 119.2(4) . . ?
C13 C14 C15 110.4(5) . . ?
C13 C14 C12 125.7(5) . . ?
C15 C14 C12 123.9(5) . . ?
C16 C15 C14 112.7(6) . . ?
C16 C15 H15 123.7 . . ?
C14 C15 H15 123.7 . . ?
C15 C16 S1 112.9(4) . . ?
C15 C16 H16 123.6 . . ?
S1 C16 H16 123.6 . . ?
C22 C17 C18 116.3(4) . . ?
C22 C17 C23 122.1(4) . . ?
C18 C17 C23 121.6(4) . . ?
C19 C18 C17 121.9(5) . . ?
C19 C18 Cl4 118.0(4) . . ?
C17 C18 Cl4 120.1(4) . . ?
C20 C19 C18 119.4(4) . . ?
C20 C19 H19 120.3 . . ?
C18 C19 H19 120.3 . . ?
C19 C20 C21 121.2(5) . . ?
C19 C20 Cl5 119.6(4) . . ?
C21 C20 Cl5 119.2(5) . . ?
C22 C21 C20 118.5(5) . . ?
C22 C21 H21 120.8 . . ?
C20 C21 H21 120.8 . . ?
C21 C22 C17 122.7(4) . . ?
C21 C22 H22 118.7 . . ?
C17 C22 H22 118.7 . . ?
O2 C23 C24 105.7(4) . . ?
O2 C23 C17 110.1(4) . . ?
C24 C23 C17 112.1(4) . . ?
O2 C23 H23 109.6 . . ?
C24 C23 H23 109.6 . . ?
C17 C23 H23 109.6 . . ?
N3 C24 C23 110.0(4) . . ?
N3 C24 H24A 109.7 . . ?
C23 C24 H24A 109.7 . . ?
N3 C24 H24B 109.7 . . ?
C23 C24 H24B 109.7 . . ?
H24A C24 H24B 108.2 . . ?
N4 C25 N3 110.3(5) . . ?
N4 C25 H25 124.8 . . ?
N3 C25 H25 124.8 . . ?
C27 C26 N4 107.3(6) . . ?
C27 C26 H26 126.3 . . ?
N4 C26 H26 126.3 . . ?
C26 C27 N3 107.8(5) . . ?
C26 C27 H27 126.1 . . ?
N3 C27 H27 126.1 . . ?
O2 C28 C30 110.0(4) . . ?
O2 C28 H28A 109.7 . . ?
C30 C28 H28A 109.7 . . ?
O2 C28 H28B 109.7 . . ?
C30 C28 H28B 109.7 . . ?
H28A C28 H28B 108.2 . . ?
C30 C29 S2 113.7(4) . . ?
C30 C29 Cl6 127.3(4) . . ?
S2 C29 Cl6 119.0(4) . . ?
C29 C30 C31 110.7(5) . . ?
C29 C30 C28 125.8(5) . . ?
C31 C30 C28 123.4(5) . . ?
C32 C31 C30 111.9(6) . . ?
C32 C31 H31 124.0 . . ?
C30 C31 H31 124.0 . . ?
C31 C32 S2 113.0(4) . . ?
C31 C32 H32 123.5 . . ?
S2 C32 H32 123.5 . . ?
O3 C33 O4 125.3(5) . . ?
O3 C33 C34 118.0(5) . . ?
O4 C33 C34 116.7(5) . . ?
C35 C34 C33 123.5(5) . . ?
C35 C34 H34 118.2 . . ?
C33 C34 H34 118.2 . . ?
C34 C35 C36 121.4(5) . . ?
C34 C35 H35 119.3 . . ?
C36 C35 H35 119.3 . . ?
O5 C36 O6 122.4(5) . . ?
O5 C36 C35 125.7(6) . . ?
O6 C36 C35 112.0(5) . . ?
O7 C37 O8 124.7(5) . . ?
O7 C37 C38 118.5(5) . . ?
O8 C37 C38 116.7(5) . . ?
C39 C38 C37 124.2(5) . . ?
C39 C38 H38 117.9 . . ?
C37 C38 H38 117.9 . . ?
C38 C39 C40 122.4(5) . . ?
C38 C39 H39 118.8 . . ?
C40 C39 H39 118.8 . . ?
O9 C40 O10 124.5(5) . . ?
O9 C40 C39 123.1(5) . . ?
O10 C40 C39 112.4(5) . . ?
C9 N1 C11 106.8(4) . . ?
C9 N1 C8 126.3(5) . . ?
C11 N1 C8 126.3(4) . . ?
C9 N2 C10 108.7(5) . . ?
C9 N2 H2N 129(4) . . ?
C10 N2 H2N 121(4) . . ?
C25 N3 C27 106.9(4) . . ?
C25 N3 C24 126.1(5) . . ?
C27 N3 C24 126.6(4) . . ?
C25 N4 C26 107.7(5) . . ?
C25 N4 H4N 130(5) . . ?
C26 N4 H4N 123(5) . . ?
C12 O1 C7 113.0(3) . . ?
C28 O2 C23 113.0(3) . . ?
C36 O6 H6O 109.5 . . ?
C40 O10 H10O 106(6) . . ?
H11A O11 H11B 85(7) . . ?
C16 S1 C13 90.1(3) . . ?
C32 S2 C29 90.7(3) . . ?

_refine_diff_density_max         0.385
_refine_diff_density_min         -0.418
_refine_diff_density_rms         0.085

####################################################################### 
# 
# 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_TCZ-LTAC
_database_code_depnum_ccdc_archive 'CCDC 2285611'
loop_
_audit_author_name
_audit_author_address
'Tejender Thakur'
;CSIR Central Drug Research Institute
India
;
_audit_update_record             
;
2023-07-31 deposited with the CCDC.	2023-11-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            
'Tiaconazole-L-tartrate-L-tartaric acid (2:2:1)salt cocrystal'
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C16 H14 Cl3 N2 O S), 2(C4 H5 O6), C4 H6 O6'
_chemical_formula_sum            'C22 H22 Cl3 N2 O10 S'
_chemical_formula_weight         612.82

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'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           1
_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'

_cell_length_a                   7.5563(2)
_cell_length_b                   8.3022(2)
_cell_length_c                   20.6593(5)
_cell_angle_alpha                83.732(2)
_cell_angle_beta                 82.528(2)
_cell_angle_gamma                89.714(2)
_cell_volume                     1277.30(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    23827
_cell_measurement_theta_min      2.1650
_cell_measurement_theta_max      72.5090

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.593
_exptl_crystal_F_000             630
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.330
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    4.552
_shelx_estimated_absorpt_T_min   0.315
_shelx_estimated_absorpt_T_max   0.659
_exptl_absorpt_correction_T_min  0.39793
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_source_power             0.0
_diffrn_source_voltage           50.0
_diffrn_source_current           0.6
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   MicroMax003_Cu
_diffrn_radiation_monochromator  Confocal
_diffrn_measurement_specimen_support Loop
_diffrn_detector                 CCD
_diffrn_measurement_device       
;
AFC12 (Right): Kappa 3 circle
;
_diffrn_measurement_device_type  
;
Rigaku Saturn724+ (4x4 bin mode)
;
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_reflns_number            25653
_diffrn_reflns_av_unetI/netI     0.0600
_diffrn_reflns_av_R_equivalents  0.0947
_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       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.170
_diffrn_reflns_theta_max         72.705
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.943
_diffrn_measured_fraction_theta_full 0.966
_diffrn_reflns_Laue_measured_fraction_max 0.943
_diffrn_reflns_Laue_measured_fraction_full 0.966
_diffrn_reflns_point_group_measured_fraction_max 0.795
_diffrn_reflns_point_group_measured_fraction_full 0.826
_reflns_number_total             8086
_reflns_number_gt                7976
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.685
_reflns_Friedel_fraction_max     0.646
_reflns_Friedel_fraction_full    0.687

_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       'CrystalClear-SM Expert 2.1 b28 (Rigaku, 2013)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_structure_solution    'SHELXS-2013/1 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'
_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)+(0.1196P)²+0.1384P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   direct
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.0198(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   0.021(13)
_chemical_absolute_configuration .
_refine_ls_number_reflns         8086
_refine_ls_number_parameters     709
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0568
_refine_ls_R_factor_gt           0.0532
_refine_ls_wR_factor_ref         0.1402
_refine_ls_wR_factor_gt          0.1376
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.043
_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
C1 C 0.7393(6) 0.4361(6) 0.7186(2) 0.0178(9) Uani 1 1 d . . . . .
C2 C 0.6321(6) 0.4903(6) 0.6700(2) 0.0195(9) Uani 1 1 d . . . . .
C3 C 0.5684(6) 0.3883(6) 0.6296(2) 0.0215(9) Uani 1 1 d . . . . .
H3 H 0.494752 0.427741 0.597511 0.026 Uiso 1 1 calc R U . . .
C4 C 0.6152(6) 0.2278(6) 0.6372(2) 0.0222(10) Uani 1 1 d . . . . .
C5 C 0.7258(7) 0.1682(6) 0.6827(2) 0.0247(10) Uani 1 1 d . . . . .
H5 H 0.760102 0.057665 0.685964 0.030 Uiso 1 1 calc R U . . .
C6 C 0.7850(7) 0.2726(6) 0.7232(2) 0.0228(10) Uani 1 1 d . . . . .
H6 H 0.858971 0.231984 0.754961 0.027 Uiso 1 1 calc R U . . .
C7 C 0.7980(6) 0.5497(6) 0.7646(2) 0.0183(9) Uani 1 1 d . . . . .
H7 H 0.835054 0.656034 0.738980 0.022 Uiso 1 1 calc R U . . .
C8 C 0.6431(6) 0.5764(6) 0.8178(2) 0.0220(10) Uani 1 1 d . . . . .
H8A H 0.532013 0.594947 0.797537 0.026 Uiso 1 1 calc R U . . .
H8B H 0.625439 0.478171 0.849820 0.026 Uiso 1 1 calc R U . . .
C9 C 0.7502(6) 0.7076(6) 0.9082(2) 0.0201(9) Uani 1 1 d . . . . .
H9 H 0.783336 0.611321 0.932805 0.024 Uiso 1 1 calc R U . . .
C10 C 0.7065(7) 0.9651(6) 0.8759(2) 0.0240(10) Uani 1 1 d . . . . .
H10 H 0.704707 1.079753 0.874843 0.029 Uiso 1 1 calc R U . . .
C11 C 0.6510(6) 0.8767(6) 0.8312(2) 0.0228(10) Uani 1 1 d . . . . .
H11 H 0.601899 0.917494 0.792702 0.027 Uiso 1 1 calc R U . . .
C12 C 1.1163(6) 0.5340(6) 0.7615(2) 0.0213(10) Uani 1 1 d . . . . .
H12A H 1.116836 0.528771 0.713851 0.026 Uiso 1 1 calc R U . . .
H12B H 1.208734 0.459704 0.776903 0.026 Uiso 1 1 calc R U . . .
C13 C 1.1611(6) 0.8399(6) 0.7300(2) 0.0227(10) Uani 1 1 d . . . . .
C14 C 1.1565(6) 0.7051(6) 0.7741(2) 0.0190(9) Uani 1 1 d . . . . .
C15 C 1.1888(7) 0.7471(7) 0.8371(2) 0.0244(10) Uani 1 1 d . . . . .
H15 H 1.191268 0.669988 0.874467 0.029 Uiso 1 1 calc R U . . .
C16 C 1.2154(7) 0.9074(7) 0.8378(3) 0.0263(10) Uani 1 1 d . . . . .
H16 H 1.237764 0.955324 0.875704 0.032 Uiso 1 1 calc R U . . .
C17 C 0.8611(6) 1.1703(6) 0.4371(2) 0.0179(9) Uani 1 1 d . . . . .
C18 C 0.9719(6) 1.1141(6) 0.4838(2) 0.0177(9) Uani 1 1 d . . . . .
C19 C 1.0387(7) 1.2152(6) 0.5242(2) 0.0227(10) Uani 1 1 d . . . . .
H19 H 1.114902 1.174724 0.555229 0.027 Uiso 1 1 calc R U . . .
C20 C 0.9915(7) 1.3757(6) 0.5180(2) 0.0229(10) Uani 1 1 d . . . . .
C21 C 0.8767(7) 1.4367(6) 0.4745(2) 0.0238(10) Uani 1 1 d . . . . .
H21 H 0.841371 1.546896 0.472458 0.029 Uiso 1 1 calc R U . . .
C22 C 0.8140(7) 1.3329(6) 0.4336(2) 0.0218(9) Uani 1 1 d . . . . .
H22 H 0.737517 1.374147 0.402828 0.026 Uiso 1 1 calc R U . . .
C23 C 0.7979(6) 1.0585(6) 0.3911(2) 0.0166(9) Uani 1 1 d . . . . .
H23 H 0.763360 0.950976 0.416228 0.020 Uiso 1 1 calc R U . . .
C24 C 0.9493(6) 1.0354(6) 0.3360(2) 0.0178(9) Uani 1 1 d . . . . .
H24A H 0.968107 1.136642 0.305824 0.021 Uiso 1 1 calc R U . . .
H24B H 1.061320 1.010417 0.354987 0.021 Uiso 1 1 calc R U . . .
C25 C 0.8359(6) 0.9210(6) 0.2436(2) 0.0167(9) Uani 1 1 d . . . . .
H25 H 0.817546 1.020819 0.218263 0.020 Uiso 1 1 calc R U . . .
C26 C 0.8432(7) 0.6603(6) 0.2765(2) 0.0233(10) Uani 1 1 d . . . . .
H26 H 0.831426 0.546081 0.277636 0.028 Uiso 1 1 calc R U . . .
C27 C 0.9086(7) 0.7409(6) 0.3222(2) 0.0238(10) Uani 1 1 d . . . . .
H27 H 0.949185 0.694515 0.361705 0.029 Uiso 1 1 calc R U . . .
C28 C 0.4788(6) 1.0642(6) 0.3943(2) 0.0191(9) Uani 1 1 d . . . . .
H28A H 0.384053 1.138064 0.380554 0.023 Uiso 1 1 calc R U . . .
H28B H 0.477178 1.063329 0.442346 0.023 Uiso 1 1 calc R U . . .
C29 C 0.4417(6) 0.7583(6) 0.4212(2) 0.0215(10) Uani 1 1 d . . . . .
C30 C 0.4413(6) 0.8973(6) 0.3788(2) 0.0195(10) Uani 1 1 d . . . . .
C31 C 0.3973(6) 0.8601(6) 0.3166(2) 0.0216(10) Uani 1 1 d . . . . .
H31 H 0.389502 0.940249 0.280577 0.026 Uiso 1 1 calc R U . . .
C32 C 0.3680(7) 0.7004(7) 0.3139(2) 0.0270(11) Uani 1 1 d . . . . .
H32 H 0.338316 0.656170 0.276145 0.032 Uiso 1 1 calc R U . . .
C33 C 0.5294(6) 0.7394(5) 0.0815(2) 0.0160(9) Uani 1 1 d . . . . .
C34 C 0.3740(6) 0.8289(6) 0.0550(2) 0.0167(9) Uani 1 1 d . . . . .
H34 H 0.370951 0.808525 0.008300 0.020 Uiso 1 1 calc R U . . .
C35 C 0.1994(6) 0.7648(6) 0.0975(2) 0.0151(9) Uani 1 1 d . . . . .
H35 H 0.191693 0.645632 0.094521 0.018 Uiso 1 1 calc R U . . .
C36 C 0.0454(6) 0.8444(6) 0.0659(2) 0.0170(9) Uani 1 1 d . . . . .
C37 C 0.7437(6) 0.3854(5) 0.1722(2) 0.0154(8) Uani 1 1 d . . . . .
C38 C 0.5433(5) 0.3725(5) 0.19437(19) 0.0138(8) Uani 1 1 d . . . . .
H38 H 0.488113 0.478962 0.181533 0.017 Uiso 1 1 calc R U . . .
C39 C 0.4664(5) 0.2428(5) 0.1576(2) 0.0151(8) Uani 1 1 d . . . . .
H39 H 0.489857 0.275516 0.109176 0.018 Uiso 1 1 calc R U . . .
C40 C 0.2662(6) 0.2270(5) 0.1788(2) 0.0162(9) Uani 1 1 d . . . . .
C41 C 0.2905(6) 0.2761(5) 0.9293(2) 0.0185(9) Uani 1 1 d . . . . .
C42 C 0.0982(6) 0.2155(6) 0.9433(2) 0.0157(8) Uani 1 1 d . . . . .
H42 H 0.102061 0.100606 0.963385 0.019 Uiso 1 1 calc R U . . .
C43 C -0.0124(6) 0.3086(6) 0.9940(2) 0.0175(9) Uani 1 1 d . . . . .
H43 H 0.028945 0.284263 1.038030 0.021 Uiso 1 1 calc R U . . .
C44 C -0.2067(5) 0.2544(5) 0.99654(19) 0.0142(8) Uani 1 1 d . . . . .
N1 N 0.6790(5) 0.7158(5) 0.85200(18) 0.0181(8) Uani 1 1 d . . . . .
N2 N 0.7664(5) 0.8563(5) 0.92366(19) 0.0206(8) Uani 1 1 d . . . . .
N3 N 0.9044(5) 0.9036(5) 0.29997(18) 0.0164(8) Uani 1 1 d . . . . .
N4 N 0.7973(5) 0.7742(5) 0.22859(19) 0.0187(8) Uani 1 1 d . . . . .
O1 O 0.9421(4) 0.4853(4) 0.79646(15) 0.0201(7) Uani 1 1 d . . . . .
O2 O 0.6506(4) 1.1234(4) 0.36119(14) 0.0185(7) Uani 1 1 d . . . . .
O3 O 0.5620(4) 0.6016(4) 0.05903(15) 0.0191(6) Uani 1 1 d . . . . .
O4 O 0.6125(4) 0.7971(4) 0.12111(17) 0.0227(7) Uani 1 1 d . . . . .
O5 O 0.3842(5) 0.9958(4) 0.05888(19) 0.0273(8) Uani 1 1 d . . . . .
H5A H 0.489282 1.028638 0.046265 0.041 Uiso 1 1 calc R U . . .
O6 O 0.1988(4) 0.7870(4) 0.16362(14) 0.0197(6) Uani 1 1 d . . . . .
H6A H 0.197012 0.886550 0.167742 0.030 Uiso 1 1 calc R U . . .
O7 O 0.0032(5) 0.7987(4) 0.01500(16) 0.0239(7) Uani 1 1 d . . . . .
O8 O -0.0296(4) 0.9650(4) 0.09424(15) 0.0195(7) Uani 1 1 d . . . . .
H8 H -0.095093 1.015590 0.069200 0.029 Uiso 1 1 calc R U . . .
O9 O 0.8461(4) 0.3254(4) 0.21125(15) 0.0204(7) Uani 1 1 d . . . . .
O10 O 0.7955(4) 0.4543(4) 0.11452(15) 0.0194(7) Uani 1 1 d . . . . .
O11 O 0.5041(4) 0.3351(4) 0.26325(14) 0.0191(6) Uani 1 1 d . . . . .
H11A H 0.585645 0.277568 0.277280 0.029 Uiso 1 1 calc R U . . .
O12 O 0.5571(4) 0.0985(4) 0.17333(15) 0.0180(6) Uani 1 1 d . . . . .
H12 H 0.537980 0.031088 0.147489 0.027 Uiso 1 1 calc R U . . .
O13 O 0.1820(4) 0.3624(4) 0.16658(18) 0.0243(7) Uani 1 1 d . . . . .
H13 H 0.072288 0.348082 0.178987 0.036 Uiso 1 1 calc R U . . .
O14 O 0.1940(4) 0.0992(4) 0.20408(15) 0.0196(7) Uani 1 1 d . . . . .
O15 O 0.3564(5) 0.3058(6) 0.98274(18) 0.0367(10) Uani 1 1 d . . . . .
H15A H 0.468366 0.309849 0.975126 0.055 Uiso 1 1 calc R U . . .
O16 O 0.3703(5) 0.2945(6) 0.87448(18) 0.0416(10) Uani 1 1 d . . . . .
O17 O 0.0179(4) 0.2127(5) 0.88557(15) 0.0201(7) Uani 1 1 d . . . . .
O18 O 0.0118(4) 0.4755(4) 0.97124(16) 0.0218(7) Uani 1 1 d . . . . .
H18 H 0.012441 0.528944 1.003457 0.033 Uiso 1 1 calc R U . . .
O19 O -0.2495(4) 0.1126(4) 1.02345(15) 0.0182(6) Uani 1 1 d . . . . .
O20 O -0.3092(4) 0.3504(4) 0.96941(16) 0.0207(7) Uani 1 1 d . . . . .
S1 S 1.20425(16) 1.01520(14) 0.76279(6) 0.0266(3) Uani 1 1 d . . . . .
S2 S 0.39121(16) 0.58638(15) 0.38758(6) 0.0281(3) Uani 1 1 d . . . . .
Cl1 Cl 0.57884(15) 0.69531(13) 0.65846(6) 0.0261(3) Uani 1 1 d . . . . .
Cl2 Cl 0.53563(17) 0.09527(15) 0.58732(6) 0.0299(3) Uani 1 1 d . . . . .
Cl3 Cl 1.12183(15) 0.84828(14) 0.64932(5) 0.0264(3) Uani 1 1 d . . . . .
Cl4 Cl 1.02838(15) 0.90946(13) 0.49314(5) 0.0258(3) Uani 1 1 d . . . . .
Cl5 Cl 1.07439(17) 1.50477(15) 0.56844(6) 0.0314(3) Uani 1 1 d . . . . .
Cl6 Cl 0.48965(15) 0.74386(14) 0.50128(5) 0.0265(3) Uani 1 1 d . . . . .
H2N H 0.815(10) 0.873(9) 0.956(4) 0.041(19) Uiso 1 1 d . . . . .
H3O H 0.665(10) 0.546(9) 0.076(4) 0.041(18) Uiso 1 1 d . . . . .
H4N H 0.766(8) 0.753(8) 0.187(3) 0.028(15) Uiso 1 1 d . . . . .
H17O H 0.016(11) 0.295(10) 0.876(4) 0.04(2) 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
C1 C6 1.395(7) . ?
C1 C2 1.406(6) . ?
C1 C7 1.515(6) . ?
C2 C3 1.381(7) . ?
C2 Cl1 1.745(5) . ?
C3 C4 1.374(8) . ?
C3 H3 0.9500 . ?
C4 C5 1.387(7) . ?
C4 Cl2 1.747(5) . ?
C5 C6 1.383(7) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 O1 1.418(5) . ?
C7 C8 1.531(6) . ?
C7 H7 1.0000 . ?
C8 N1 1.464(6) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 N2 1.318(7) . ?
C9 N1 1.337(6) . ?
C9 H9 0.9500 . ?
C10 C11 1.348(7) . ?
C10 N2 1.382(6) . ?
C10 H10 0.9500 . ?
C11 N1 1.382(6) . ?
C11 H11 0.9500 . ?
C12 O1 1.453(5) . ?
C12 C14 1.511(7) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.361(7) . ?
C13 S1 1.720(5) . ?
C13 Cl3 1.725(5) . ?
C14 C15 1.434(6) . ?
C15 C16 1.349(8) . ?
C15 H15 0.9500 . ?
C16 S1 1.715(5) . ?
C16 H16 0.9500 . ?
C17 C22 1.391(7) . ?
C17 C18 1.400(6) . ?
C17 C23 1.519(6) . ?
C18 C19 1.386(6) . ?
C18 Cl4 1.746(5) . ?
C19 C20 1.375(8) . ?
C19 H19 0.9500 . ?
C20 C21 1.384(7) . ?
C20 Cl5 1.747(5) . ?
C21 C22 1.394(7) . ?
C21 H21 0.9500 . ?
C22 H22 0.9500 . ?
C23 O2 1.419(5) . ?
C23 C24 1.531(6) . ?
C23 H23 1.0000 . ?
C24 N3 1.454(6) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C25 N3 1.329(5) . ?
C25 N4 1.332(6) . ?
C25 H25 0.9500 . ?
C26 C27 1.359(7) . ?
C26 N4 1.370(6) . ?
C26 H26 0.9500 . ?
C27 N3 1.380(6) . ?
C27 H27 0.9500 . ?
C28 O2 1.448(5) . ?
C28 C30 1.492(7) . ?
C28 H28A 0.9900 . ?
C28 H28B 0.9900 . ?
C29 C30 1.370(7) . ?
C29 S2 1.719(5) . ?
C29 Cl6 1.731(5) . ?
C30 C31 1.434(7) . ?
C31 C32 1.354(7) . ?
C31 H31 0.9500 . ?
C32 S2 1.731(5) . ?
C32 H32 0.9500 . ?
C33 O4 1.231(5) . ?
C33 O3 1.292(6) . ?
C33 C34 1.517(6) . ?
C34 O5 1.400(6) . ?
C34 C35 1.549(5) . ?
C34 H34 1.0000 . ?
C35 O6 1.399(5) . ?
C35 C36 1.520(6) . ?
C35 H35 1.0000 . ?
C36 O7 1.236(5) . ?
C36 O8 1.305(6) . ?
C37 O9 1.253(5) . ?
C37 O10 1.277(5) . ?
C37 C38 1.525(6) . ?
C38 O11 1.416(5) . ?
C38 C39 1.541(6) . ?
C38 H38 1.0000 . ?
C39 O12 1.405(5) . ?
C39 C40 1.522(5) . ?
C39 H39 1.0000 . ?
C40 O14 1.227(5) . ?
C40 O13 1.306(6) . ?
C41 O16 1.206(6) . ?
C41 O15 1.316(6) . ?
C41 C42 1.521(6) . ?
C42 O17 1.408(5) . ?
C42 C43 1.529(6) . ?
C42 H42 1.0000 . ?
C43 O18 1.419(6) . ?
C43 C44 1.530(6) . ?
C43 H43 1.0000 . ?
C44 O20 1.249(5) . ?
C44 O19 1.271(5) . ?
N2 H2N 0.83(8) . ?
N4 H4N 0.96(6) . ?
O3 H3O 0.98(8) . ?
O5 H5A 0.8400 . ?
O6 H6A 0.8400 . ?
O8 H8 0.8400 . ?
O11 H11A 0.8400 . ?
O12 H12 0.8400 . ?
O13 H13 0.8400 . ?
O15 H15A 0.8400 . ?
O17 H17O 0.69(8) . ?
O18 H18 0.8400 . ?

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

C6 C1 C2 116.7(4) . . ?
C6 C1 C7 122.0(4) . . ?
C2 C1 C7 121.3(4) . . ?
C3 C2 C1 122.8(5) . . ?
C3 C2 Cl1 117.9(4) . . ?
C1 C2 Cl1 119.3(4) . . ?
C4 C3 C2 117.8(4) . . ?
C4 C3 H3 121.1 . . ?
C2 C3 H3 121.1 . . ?
C3 C4 C5 122.1(5) . . ?
C3 C4 Cl2 119.0(4) . . ?
C5 C4 Cl2 118.9(4) . . ?
C6 C5 C4 118.8(5) . . ?
C6 C5 H5 120.6 . . ?
C4 C5 H5 120.6 . . ?
C5 C6 C1 121.8(4) . . ?
C5 C6 H6 119.1 . . ?
C1 C6 H6 119.1 . . ?
O1 C7 C1 111.7(4) . . ?
O1 C7 C8 107.6(3) . . ?
C1 C7 C8 109.8(3) . . ?
O1 C7 H7 109.2 . . ?
C1 C7 H7 109.2 . . ?
C8 C7 H7 109.2 . . ?
N1 C8 C7 110.8(4) . . ?
N1 C8 H8A 109.5 . . ?
C7 C8 H8A 109.5 . . ?
N1 C8 H8B 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 108.1 . . ?
N2 C9 N1 108.2(4) . . ?
N2 C9 H9 125.9 . . ?
N1 C9 H9 125.9 . . ?
C11 C10 N2 106.7(4) . . ?
C11 C10 H10 126.7 . . ?
N2 C10 H10 126.7 . . ?
C10 C11 N1 107.1(4) . . ?
C10 C11 H11 126.4 . . ?
N1 C11 H11 126.4 . . ?
O1 C12 C14 108.9(4) . . ?
O1 C12 H12A 109.9 . . ?
C14 C12 H12A 109.9 . . ?
O1 C12 H12B 109.9 . . ?
C14 C12 H12B 109.9 . . ?
H12A C12 H12B 108.3 . . ?
C14 C13 S1 113.3(4) . . ?
C14 C13 Cl3 126.6(4) . . ?
S1 C13 Cl3 120.0(3) . . ?
C13 C14 C15 110.5(5) . . ?
C13 C14 C12 126.4(4) . . ?
C15 C14 C12 123.0(4) . . ?
C16 C15 C14 113.1(5) . . ?
C16 C15 H15 123.5 . . ?
C14 C15 H15 123.5 . . ?
C15 C16 S1 112.5(4) . . ?
C15 C16 H16 123.7 . . ?
S1 C16 H16 123.7 . . ?
C22 C17 C18 117.4(4) . . ?
C22 C17 C23 121.5(4) . . ?
C18 C17 C23 121.1(4) . . ?
C19 C18 C17 122.4(4) . . ?
C19 C18 Cl4 117.8(3) . . ?
C17 C18 Cl4 119.8(3) . . ?
C20 C19 C18 118.0(4) . . ?
C20 C19 H19 121.0 . . ?
C18 C19 H19 121.0 . . ?
C19 C20 C21 122.1(4) . . ?
C19 C20 Cl5 118.6(4) . . ?
C21 C20 Cl5 119.2(4) . . ?
C20 C21 C22 118.6(5) . . ?
C20 C21 H21 120.7 . . ?
C22 C21 H21 120.7 . . ?
C17 C22 C21 121.4(4) . . ?
C17 C22 H22 119.3 . . ?
C21 C22 H22 119.3 . . ?
O2 C23 C17 111.9(4) . . ?
O2 C23 C24 107.4(3) . . ?
C17 C23 C24 109.4(3) . . ?
O2 C23 H23 109.4 . . ?
C17 C23 H23 109.4 . . ?
C24 C23 H23 109.4 . . ?
N3 C24 C23 109.8(3) . . ?
N3 C24 H24A 109.7 . . ?
C23 C24 H24A 109.7 . . ?
N3 C24 H24B 109.7 . . ?
C23 C24 H24B 109.7 . . ?
H24A C24 H24B 108.2 . . ?
N3 C25 N4 108.2(4) . . ?
N3 C25 H25 125.9 . . ?
N4 C25 H25 125.9 . . ?
C27 C26 N4 107.3(4) . . ?
C27 C26 H26 126.4 . . ?
N4 C26 H26 126.4 . . ?
C26 C27 N3 106.4(4) . . ?
C26 C27 H27 126.8 . . ?
N3 C27 H27 126.8 . . ?
O2 C28 C30 111.2(4) . . ?
O2 C28 H28A 109.4 . . ?
C30 C28 H28A 109.4 . . ?
O2 C28 H28B 109.4 . . ?
C30 C28 H28B 109.4 . . ?
H28A C28 H28B 108.0 . . ?
C30 C29 S2 113.7(4) . . ?
C30 C29 Cl6 126.4(4) . . ?
S2 C29 Cl6 119.8(3) . . ?
C29 C30 C31 110.1(4) . . ?
C29 C30 C28 125.8(4) . . ?
C31 C30 C28 124.2(4) . . ?
C32 C31 C30 113.8(4) . . ?
C32 C31 H31 123.1 . . ?
C30 C31 H31 123.1 . . ?
C31 C32 S2 111.8(4) . . ?
C31 C32 H32 124.1 . . ?
S2 C32 H32 124.1 . . ?
O4 C33 O3 125.1(4) . . ?
O4 C33 C34 121.0(4) . . ?
O3 C33 C34 113.9(4) . . ?
O5 C34 C33 111.9(3) . . ?
O5 C34 C35 107.6(4) . . ?
C33 C34 C35 108.2(3) . . ?
O5 C34 H34 109.7 . . ?
C33 C34 H34 109.7 . . ?
C35 C34 H34 109.7 . . ?
O6 C35 C36 114.6(4) . . ?
O6 C35 C34 112.0(3) . . ?
C36 C35 C34 107.1(3) . . ?
O6 C35 H35 107.7 . . ?
C36 C35 H35 107.7 . . ?
C34 C35 H35 107.7 . . ?
O7 C36 O8 124.0(4) . . ?
O7 C36 C35 120.1(4) . . ?
O8 C36 C35 115.8(4) . . ?
O9 C37 O10 124.5(4) . . ?
O9 C37 C38 117.8(4) . . ?
O10 C37 C38 117.7(4) . . ?
O11 C38 C37 112.0(3) . . ?
O11 C38 C39 111.3(3) . . ?
C37 C38 C39 108.0(3) . . ?
O11 C38 H38 108.5 . . ?
C37 C38 H38 108.5 . . ?
C39 C38 H38 108.5 . . ?
O12 C39 C40 112.4(3) . . ?
O12 C39 C38 106.4(3) . . ?
C40 C39 C38 109.2(3) . . ?
O12 C39 H39 109.6 . . ?
C40 C39 H39 109.6 . . ?
C38 C39 H39 109.6 . . ?
O14 C40 O13 124.5(4) . . ?
O14 C40 C39 122.7(4) . . ?
O13 C40 C39 112.7(4) . . ?
O16 C41 O15 125.0(4) . . ?
O16 C41 C42 122.2(4) . . ?
O15 C41 C42 112.8(3) . . ?
O17 C42 C41 112.5(3) . . ?
O17 C42 C43 112.3(4) . . ?
C41 C42 C43 111.8(3) . . ?
O17 C42 H42 106.6 . . ?
C41 C42 H42 106.6 . . ?
C43 C42 H42 106.6 . . ?
O18 C43 C42 106.5(3) . . ?
O18 C43 C44 111.8(4) . . ?
C42 C43 C44 106.9(3) . . ?
O18 C43 H43 110.5 . . ?
C42 C43 H43 110.5 . . ?
C44 C43 H43 110.5 . . ?
O20 C44 O19 124.9(4) . . ?
O20 C44 C43 117.4(4) . . ?
O19 C44 C43 117.6(4) . . ?
C9 N1 C11 108.6(4) . . ?
C9 N1 C8 125.0(4) . . ?
C11 N1 C8 126.4(4) . . ?
C9 N2 C10 109.4(4) . . ?
C9 N2 H2N 120(5) . . ?
C10 N2 H2N 130(5) . . ?
C25 N3 C27 109.1(4) . . ?
C25 N3 C24 125.3(4) . . ?
C27 N3 C24 125.2(4) . . ?
C25 N4 C26 109.0(4) . . ?
C25 N4 H4N 124(4) . . ?
C26 N4 H4N 126(4) . . ?
C7 O1 C12 113.5(3) . . ?
C23 O2 C28 114.0(3) . . ?
C33 O3 H3O 113(4) . . ?
C34 O5 H5A 109.5 . . ?
C35 O6 H6A 109.5 . . ?
C36 O8 H8 109.5 . . ?
C38 O11 H11A 109.5 . . ?
C39 O12 H12 109.5 . . ?
C40 O13 H13 109.5 . . ?
C41 O15 H15A 109.5 . . ?
C42 O17 H17O 99(7) . . ?
C43 O18 H18 109.5 . . ?
C16 S1 C13 90.5(3) . . ?
C29 S2 C32 90.5(2) . . ?

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
C6 C1 C2 C3 2.1(7) . . . . ?
C7 C1 C2 C3 -176.5(4) . . . . ?
C6 C1 C2 Cl1 -176.7(3) . . . . ?
C7 C1 C2 Cl1 4.6(6) . . . . ?
C1 C2 C3 C4 -1.0(7) . . . . ?
Cl1 C2 C3 C4 177.9(3) . . . . ?
C2 C3 C4 C5 -1.4(7) . . . . ?
C2 C3 C4 Cl2 179.5(3) . . . . ?
C3 C4 C5 C6 2.5(7) . . . . ?
Cl2 C4 C5 C6 -178.5(3) . . . . ?
C4 C5 C6 C1 -1.2(7) . . . . ?
C2 C1 C6 C5 -1.0(7) . . . . ?
C7 C1 C6 C5 177.6(4) . . . . ?
C6 C1 C7 O1 17.9(6) . . . . ?
C2 C1 C7 O1 -163.5(4) . . . . ?
C6 C1 C7 C8 -101.4(5) . . . . ?
C2 C1 C7 C8 77.2(5) . . . . ?
O1 C7 C8 N1 73.1(5) . . . . ?
C1 C7 C8 N1 -165.1(4) . . . . ?
N2 C10 C11 N1 -0.4(5) . . . . ?
S1 C13 C14 C15 0.2(5) . . . . ?
Cl3 C13 C14 C15 -177.6(4) . . . . ?
S1 C13 C14 C12 177.9(4) . . . . ?
Cl3 C13 C14 C12 0.1(7) . . . . ?
O1 C12 C14 C13 -109.2(5) . . . . ?
O1 C12 C14 C15 68.2(6) . . . . ?
C13 C14 C15 C16 0.1(6) . . . . ?
C12 C14 C15 C16 -177.7(4) . . . . ?
C14 C15 C16 S1 -0.4(6) . . . . ?
C22 C17 C18 C19 -2.1(6) . . . . ?
C23 C17 C18 C19 176.8(4) . . . . ?
C22 C17 C18 Cl4 177.2(3) . . . . ?
C23 C17 C18 Cl4 -3.9(6) . . . . ?
C17 C18 C19 C20 0.7(7) . . . . ?
Cl4 C18 C19 C20 -178.6(3) . . . . ?
C18 C19 C20 C21 1.9(7) . . . . ?
C18 C19 C20 Cl5 -180.0(3) . . . . ?
C19 C20 C21 C22 -3.0(7) . . . . ?
Cl5 C20 C21 C22 178.9(3) . . . . ?
C18 C17 C22 C21 0.9(7) . . . . ?
C23 C17 C22 C21 -178.0(4) . . . . ?
C20 C21 C22 C17 1.5(7) . . . . ?
C22 C17 C23 O2 -17.8(5) . . . . ?
C18 C17 C23 O2 163.4(4) . . . . ?
C22 C17 C23 C24 101.2(5) . . . . ?
C18 C17 C23 C24 -77.7(5) . . . . ?
O2 C23 C24 N3 -70.2(4) . . . . ?
C17 C23 C24 N3 168.1(4) . . . . ?
N4 C26 C27 N3 -1.3(5) . . . . ?
S2 C29 C30 C31 0.1(5) . . . . ?
Cl6 C29 C30 C31 179.3(4) . . . . ?
S2 C29 C30 C28 179.5(3) . . . . ?
Cl6 C29 C30 C28 -1.3(7) . . . . ?
O2 C28 C30 C29 108.2(5) . . . . ?
O2 C28 C30 C31 -72.4(5) . . . . ?
C29 C30 C31 C32 -0.3(6) . . . . ?
C28 C30 C31 C32 -179.8(4) . . . . ?
C30 C31 C32 S2 0.4(5) . . . . ?
O4 C33 C34 O5 23.5(5) . . . . ?
O3 C33 C34 O5 -157.0(4) . . . . ?
O4 C33 C34 C35 -94.9(4) . . . . ?
O3 C33 C34 C35 84.6(4) . . . . ?
O5 C34 C35 O6 -62.1(4) . . . . ?
C33 C34 C35 O6 59.0(4) . . . . ?
O5 C34 C35 C36 64.2(4) . . . . ?
C33 C34 C35 C36 -174.7(4) . . . . ?
O6 C35 C36 O7 -160.2(4) . . . . ?
C34 C35 C36 O7 75.0(5) . . . . ?
O6 C35 C36 O8 22.8(5) . . . . ?
C34 C35 C36 O8 -102.0(4) . . . . ?
O9 C37 C38 O11 17.1(5) . . . . ?
O10 C37 C38 O11 -164.1(4) . . . . ?
O9 C37 C38 C39 -105.8(4) . . . . ?
O10 C37 C38 C39 73.0(5) . . . . ?
O11 C38 C39 O12 -64.9(4) . . . . ?
C37 C38 C39 O12 58.4(4) . . . . ?
O11 C38 C39 C40 56.7(4) . . . . ?
C37 C38 C39 C40 179.9(3) . . . . ?
O12 C39 C40 O14 -3.1(6) . . . . ?
C38 C39 C40 O14 -121.0(4) . . . . ?
O12 C39 C40 O13 177.5(3) . . . . ?
C38 C39 C40 O13 59.7(5) . . . . ?
O16 C41 C42 O17 -10.8(7) . . . . ?
O15 C41 C42 O17 169.0(4) . . . . ?
O16 C41 C42 C43 -138.2(5) . . . . ?
O15 C41 C42 C43 41.5(5) . . . . ?
O17 C42 C43 O18 -75.0(4) . . . . ?
C41 C42 C43 O18 52.5(4) . . . . ?
O17 C42 C43 C44 44.6(5) . . . . ?
C41 C42 C43 C44 172.1(3) . . . . ?
O18 C43 C44 O20 11.3(5) . . . . ?
C42 C43 C44 O20 -104.8(4) . . . . ?
O18 C43 C44 O19 -171.8(3) . . . . ?
C42 C43 C44 O19 72.1(4) . . . . ?
N2 C9 N1 C11 0.5(5) . . . . ?
N2 C9 N1 C8 178.7(4) . . . . ?
C10 C11 N1 C9 0.0(5) . . . . ?
C10 C11 N1 C8 -178.2(4) . . . . ?
C7 C8 N1 C9 -95.0(5) . . . . ?
C7 C8 N1 C11 82.9(6) . . . . ?
N1 C9 N2 C10 -0.8(5) . . . . ?
C11 C10 N2 C9 0.8(5) . . . . ?
N4 C25 N3 C27 -0.5(5) . . . . ?
N4 C25 N3 C24 -174.3(4) . . . . ?
C26 C27 N3 C25 1.1(5) . . . . ?
C26 C27 N3 C24 174.9(4) . . . . ?
C23 C24 N3 C25 98.0(5) . . . . ?
C23 C24 N3 C27 -74.7(5) . . . . ?
N3 C25 N4 C26 -0.3(5) . . . . ?
C27 C26 N4 C25 1.0(5) . . . . ?
C1 C7 O1 C12 91.5(4) . . . . ?
C8 C7 O1 C12 -147.9(4) . . . . ?
C14 C12 O1 C7 78.3(5) . . . . ?
C17 C23 O2 C28 -96.1(4) . . . . ?
C24 C23 O2 C28 143.8(4) . . . . ?
C30 C28 O2 C23 -77.4(5) . . . . ?
C15 C16 S1 C13 0.4(4) . . . . ?
C14 C13 S1 C16 -0.4(4) . . . . ?
Cl3 C13 S1 C16 177.6(3) . . . . ?
C30 C29 S2 C32 0.1(4) . . . . ?
Cl6 C29 S2 C32 -179.1(3) . . . . ?
C31 C32 S2 C29 -0.3(4) . . . . ?

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
_geom_hbond_publ_flag
C8 H8A Cl1 0.99 2.88 3.428(5) 115.8 . yes
C8 H8B O16 0.99 2.43 3.150(6) 129.1 . yes
C9 H9 O18 0.95 2.24 3.066(6) 144.7 1_655 yes
C9 H9 O20 0.95 2.30 3.105(6) 142.6 1_655 yes
C15 H15 O18 0.95 2.66 3.501(6) 148.4 1_655 yes
C23 H23 Cl6 1.00 2.96 3.849(4) 148.8 . yes
C24 H24A O9 0.99 2.63 3.493(5) 145.9 1_565 yes
C24 H24A O14 0.99 2.58 3.085(5) 111.9 1_665 yes
C24 H24B Cl4 0.99 2.86 3.427(4) 116.8 . yes
C25 H25 O9 0.95 2.53 3.351(6) 145.3 1_565 yes
C25 H25 O12 0.95 2.34 3.002(5) 126.2 1_565 yes
C26 H26 O9 0.95 2.40 3.218(6) 144.2 . yes
C31 H31 O12 0.95 2.62 3.457(6) 146.5 1_565 yes
C31 H31 O14 0.95 2.56 3.405(6) 148.3 1_565 yes
C35 H35 O13 1.00 2.64 3.483(5) 142.2 . yes
C38 H38 O3 1.00 2.61 3.193(5) 116.9 . yes
O5 H5A O19 0.84 2.07 2.912(5) 175.1 1_664 yes
O6 H6A O14 0.84 1.99 2.808(4) 163.8 1_565 yes
O8 H8 O19 0.84 1.74 2.573(4) 173.9 1_564 yes
O11 H11A O2 0.84 2.15 2.863(4) 142.8 1_545 yes
O11 H11A O9 0.84 2.25 2.671(4) 110.8 . yes
O12 H12 O4 0.84 2.13 2.839(5) 142.3 1_545 yes
O12 H12 O5 0.84 2.34 3.046(5) 142.5 1_545 yes
O13 H13 O9 0.84 1.75 2.593(4) 175.0 1_455 yes
O15 H15A O20 0.84 1.70 2.530(5) 168.1 1_655 yes
O18 H18 O7 0.84 2.28 2.921(5) 133.7 1_556 yes
O18 H18 O10 0.84 2.66 3.177(4) 121.5 1_456 yes
N2 H2N O7 0.83(8) 2.04(8) 2.768(5) 146(7) 1_656 yes
N2 H2N O19 0.83(8) 2.56(8) 3.111(5) 125(6) 1_665 yes
O3 H3O O10 0.98(8) 1.50(8) 2.474(4) 168(7) . yes
N4 H4N O4 0.96(6) 1.91(6) 2.762(5) 148(6) . yes
O17 H17O O1 0.69(8) 2.27(8) 2.862(5) 144(8) 1_455 yes
O17 H17O O18 0.69(8) 2.60(8) 2.952(5) 115(8) . yes
C8 H8A Cl1 0.99 2.88 3.428(5) 115.8 . yes
C8 H8B O16 0.99 2.43 3.150(6) 129.1 . yes
C9 H9 O18 0.95 2.24 3.066(6) 144.7 1_655 yes
C9 H9 O20 0.95 2.30 3.105(6) 142.6 1_655 yes
C15 H15 O18 0.95 2.66 3.501(6) 148.4 1_655 yes
C23 H23 Cl6 1.00 2.96 3.849(4) 148.8 . yes
C24 H24A O9 0.99 2.63 3.493(5) 145.9 1_565 yes
C24 H24A O14 0.99 2.58 3.085(5) 111.9 1_665 yes
C24 H24B Cl4 0.99 2.86 3.427(4) 116.8 . yes
C25 H25 O9 0.95 2.53 3.351(6) 145.3 1_565 yes
C25 H25 O12 0.95 2.34 3.002(5) 126.2 1_565 yes
C26 H26 O9 0.95 2.40 3.218(6) 144.2 . yes
C31 H31 O12 0.95 2.62 3.457(6) 146.5 1_565 yes
C31 H31 O14 0.95 2.56 3.405(6) 148.3 1_565 yes
C35 H35 O13 1.00 2.64 3.483(5) 142.2 . yes
C38 H38 O3 1.00 2.61 3.193(5) 116.9 . yes
O5 H5A O19 0.84 2.07 2.912(5) 175.1 1_664 yes
O6 H6A O14 0.84 1.99 2.808(4) 163.8 1_565 yes
O8 H8 O19 0.84 1.74 2.573(4) 173.9 1_564 yes
O11 H11A O2 0.84 2.15 2.863(4) 142.8 1_545 yes
O11 H11A O9 0.84 2.25 2.671(4) 110.8 . yes
O12 H12 O4 0.84 2.13 2.839(5) 142.3 1_545 yes
O12 H12 O5 0.84 2.34 3.046(5) 142.5 1_545 yes
O13 H13 O9 0.84 1.75 2.593(4) 175.0 1_455 yes
O15 H15A O20 0.84 1.70 2.530(5) 168.1 1_655 yes
O18 H18 O7 0.84 2.28 2.921(5) 133.7 1_556 yes
O18 H18 O10 0.84 2.66 3.177(4) 121.5 1_456 yes
N2 H2N O7 0.83(8) 2.04(8) 2.768(5) 146(7) 1_656 yes
N2 H2N O19 0.83(8) 2.56(8) 3.111(5) 125(6) 1_665 yes
O3 H3O O10 0.98(8) 1.50(8) 2.474(4) 168(7) . yes
N4 H4N O4 0.96(6) 1.91(6) 2.762(5) 148(6) . yes
O17 H17O O1 0.69(8) 2.27(8) 2.862(5) 144(8) 1_455 yes
O17 H17O O18 0.69(8) 2.60(8) 2.952(5) 115(8) . yes

_refine_diff_density_max         0.634
_refine_diff_density_min         -0.715
_refine_diff_density_rms         0.155

####################################################################### 
# 
# 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_TCZ-OXAC
_database_code_depnum_ccdc_archive 'CCDC 2285613'
loop_
_audit_author_name
_audit_author_address
'Tejender Thakur'
;CSIR Central Drug Research Institute
India
;
_audit_update_record             
;
2023-07-31 deposited with the CCDC.	2023-11-14 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT230_TCZ-OXAC            
;
PROBLEM: Hirshfeld Test Diff for    C3       --C4       .        7.5 s.u.
RESPONSE: elongated thermal ellipsoid for C3 and C4 inidicated presence of positional disorder but could not be resolved as refinement was unstable.
;
# Added during the CSD deposition process: Monday 31 July 2023 10:31 AM
# end Validation Reply Form


_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            
'Tioconazole-oxalate-oxalic acid  (1:0.5:0.5)salt cocrystal'
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H14 Cl3 N2 O S, 0.5(C2 H2 O4), 0.5(C2 O4)'
_chemical_formula_sum            'C18 H15 Cl3 N2 O5 S'
_chemical_formula_weight         477.73

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'
Cl Cl 0.3639 0.7018 '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                   10.2522(2)
_cell_length_b                   10.7638(4)
_cell_length_c                   11.0528(4)
_cell_angle_alpha                112.364(4)
_cell_angle_beta                 105.711(2)
_cell_angle_gamma                96.357(2)
_cell_volume                     1054.06(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    12802
_cell_measurement_theta_min      4.5780
_cell_measurement_theta_max      72.4630

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.505
_exptl_crystal_F_000             488
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.570
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    5.158
_shelx_estimated_absorpt_T_min   0.157
_shelx_estimated_absorpt_T_max   0.577
_exptl_absorpt_correction_T_min  0.19346
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_source_power             0.0
_diffrn_source_voltage           50.0
_diffrn_source_current           0.6
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   MicroMax003_Cu
_diffrn_radiation_monochromator  Confocal
_diffrn_measurement_specimen_support Loop
_diffrn_detector                 CCD
_diffrn_measurement_device       
;
AFC12 (Right): Kappa 3 circle
;
_diffrn_measurement_device_type  
;
Rigaku Saturn724+ (4x4 bin mode)
;
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_reflns_number            21579
_diffrn_reflns_av_unetI/netI     0.0550
_diffrn_reflns_av_R_equivalents  0.1141
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         4.576
_diffrn_reflns_theta_max         72.756
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.962
_diffrn_measured_fraction_theta_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.962
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.962
_diffrn_reflns_point_group_measured_fraction_full 0.983
_reflns_number_total             4031
_reflns_number_gt                3495
_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       'CrystalClear-SM Expert 2.1 b28 (Rigaku, 2013)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_structure_solution    'SHELXS-2013/1 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'
_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)+(0.1552P)²+1.3541P] 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     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.023(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4031
_refine_ls_number_parameters     271
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0990
_refine_ls_R_factor_gt           0.0918
_refine_ls_wR_factor_ref         0.2641
_refine_ls_wR_factor_gt          0.2553
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.041
_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
C1 C 0.1030(4) 0.2158(4) 0.7022(4) 0.0468(8) Uani 1 1 d . . . . .
C2 C 0.0010(4) 0.1781(4) 0.5752(5) 0.0576(10) Uani 1 1 d . . . . .
C3 C -0.1407(5) 0.1410(5) 0.5551(6) 0.0722(15) Uani 1 1 d . . . . .
H3 H -0.208455 0.118657 0.469776 0.087 Uiso 1 1 calc R U . . .
C4 C -0.1770(5) 0.1386(5) 0.6651(6) 0.0711(13) Uani 1 1 d . . . . .
C5 C -0.0810(5) 0.1741(5) 0.7918(6) 0.0659(12) Uani 1 1 d . . . . .
H5 H -0.108005 0.172368 0.865028 0.079 Uiso 1 1 calc R U . . .
C6 C 0.0600(4) 0.2136(4) 0.8091(5) 0.0538(10) Uani 1 1 d . . . . .
H6 H 0.126891 0.239161 0.895780 0.065 Uiso 1 1 calc R U . . .
C7 C 0.2575(3) 0.2580(4) 0.7255(4) 0.0430(8) Uani 1 1 d . . . . .
H7 H 0.278931 0.191200 0.648513 0.052 Uiso 1 1 calc R U . . .
C8 C 0.2993(3) 0.4021(4) 0.7342(4) 0.0422(8) Uani 1 1 d . . . . .
H8A H 0.231685 0.411811 0.659829 0.051 Uiso 1 1 calc R U . . .
H8B H 0.299945 0.470885 0.822182 0.051 Uiso 1 1 calc R U . . .
C9 C 0.5600(4) 0.4641(5) 0.8224(4) 0.0519(9) Uani 1 1 d . . . . .
H9 H 0.572798 0.487505 0.915671 0.062 Uiso 1 1 calc R U . . .
C10 C 0.6026(5) 0.4252(6) 0.6324(5) 0.0687(13) Uani 1 1 d . . . . .
H10 H 0.649913 0.416458 0.569799 0.082 Uiso 1 1 calc R U . . .
C11 C 0.4640(4) 0.4008(6) 0.6022(5) 0.0649(13) Uani 1 1 d . . . . .
H11 H 0.397393 0.372290 0.514728 0.078 Uiso 1 1 calc R U . . .
C12 C 0.3606(4) 0.1316(4) 0.8487(5) 0.0549(10) Uani 1 1 d . . . . .
H12A H 0.408265 0.089720 0.784337 0.066 Uiso 1 1 calc R U . . .
H12B H 0.270470 0.069659 0.819360 0.066 Uiso 1 1 calc R U . . .
C13 C 0.3962(6) 0.1442(6) 1.0901(6) 0.0718(13) Uani 1 1 d . . . . .
C14 C 0.4451(5) 0.1591(4) 0.9926(5) 0.0546(10) Uani 1 1 d . . . . .
C15 C 0.5916(5) 0.2146(5) 1.0508(6) 0.0674(12) Uani 1 1 d . . . . .
H15 H 0.645470 0.232738 1.001208 0.081 Uiso 1 1 calc R U . . .
C16 C 0.6446(6) 0.2384(6) 1.1858(6) 0.0857(18) Uani 1 1 d . . . . .
H16 H 0.738936 0.274486 1.238628 0.103 Uiso 1 1 calc R U . . .
C17 C 0.9614(3) 0.5007(4) 0.5516(4) 0.0410(8) Uani 1 1 d . . . . .
C18 C 1.0334(3) 0.5207(4) 0.9528(3) 0.0396(8) Uani 1 1 d . . . . .
N1 N 0.4382(3) 0.4254(3) 0.7228(3) 0.0402(7) Uani 1 1 d . . . . .
N2 N 0.6606(3) 0.4646(4) 0.7698(4) 0.0536(9) Uani 1 1 d . . . . .
O1 O 0.3438(2) 0.2637(3) 0.8526(3) 0.0445(6) Uani 1 1 d . . . . .
O2 O 0.8367(3) 0.4629(4) 0.5117(3) 0.0705(10) Uani 1 1 d . . . . .
O3 O 1.0457(3) 0.5446(4) 0.6766(3) 0.0543(8) Uani 1 1 d . . . . .
O4 O 0.9446(2) 0.5296(3) 0.8515(3) 0.0503(7) Uani 1 1 d . . . . .
O5 O 1.1593(2) 0.5430(3) 0.9802(3) 0.0511(7) Uani 1 1 d . . . . .
S2 S 0.5228(2) 0.19614(18) 1.24859(15) 0.0920(6) Uani 1 1 d . . . . .
Cl1 Cl 0.04498(15) 0.17535(13) 0.43310(12) 0.0745(5) Uani 1 1 d . . . . .
Cl2 Cl -0.35295(14) 0.0862(2) 0.6386(3) 0.1249(8) Uani 1 1 d . . . . .
Cl3 Cl 0.2256(2) 0.0799(3) 1.0659(3) 0.1367(10) Uani 1 1 d . . . . .
H2N H 0.754(8) 0.472(8) 0.818(9) 0.12(3) Uiso 1 1 d . . . . .
H3O H 1.001(8) 0.534(8) 0.721(8) 0.11(2) 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
C1 C6 1.376(6) . ?
C1 C2 1.380(6) . ?
C1 C7 1.521(5) . ?
C2 C3 1.396(6) . ?
C2 Cl1 1.738(5) . ?
C3 C4 1.372(8) . ?
C3 H3 0.9300 . ?
C4 C5 1.356(8) . ?
C4 Cl2 1.738(5) . ?
C5 C6 1.399(6) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 O1 1.417(4) . ?
C7 C8 1.522(5) . ?
C7 H7 0.9800 . ?
C8 N1 1.466(4) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 N2 1.314(5) . ?
C9 N1 1.318(5) . ?
C9 H9 0.9300 . ?
C10 C11 1.339(6) . ?
C10 N2 1.344(6) . ?
C10 H10 0.9300 . ?
C11 N1 1.361(5) . ?
C11 H11 0.9300 . ?
C12 O1 1.437(5) . ?
C12 C14 1.486(6) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.358(7) . ?
C13 S2 1.711(6) . ?
C13 Cl3 1.718(6) . ?
C14 C15 1.418(6) . ?
C15 C16 1.352(8) . ?
C15 H15 0.9300 . ?
C16 S2 1.684(8) . ?
C16 H16 0.9300 . ?
C17 O2 1.199(4) . ?
C17 O3 1.283(4) . ?
C17 C17 1.552(6) 2_766 ?
C18 O5 1.216(4) . ?
C18 O4 1.281(4) . ?
C18 C18 1.559(6) 2_767 ?
N2 H2N 0.94(8) . ?
O3 H3O 0.79(8) . ?

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
C6 C1 C2 117.4(4) . . ?
C6 C1 C7 120.3(3) . . ?
C2 C1 C7 122.3(4) . . ?
C1 C2 C3 121.9(5) . . ?
C1 C2 Cl1 120.9(3) . . ?
C3 C2 Cl1 117.2(4) . . ?
C4 C3 C2 117.9(5) . . ?
C4 C3 H3 121.0 . . ?
C2 C3 H3 121.0 . . ?
C5 C4 C3 122.5(4) . . ?
C5 C4 Cl2 119.4(4) . . ?
C3 C4 Cl2 118.1(4) . . ?
C4 C5 C6 118.1(5) . . ?
C4 C5 H5 121.0 . . ?
C6 C5 H5 121.0 . . ?
C1 C6 C5 122.1(4) . . ?
C1 C6 H6 118.9 . . ?
C5 C6 H6 118.9 . . ?
O1 C7 C1 112.5(3) . . ?
O1 C7 C8 105.1(3) . . ?
C1 C7 C8 112.2(3) . . ?
O1 C7 H7 109.0 . . ?
C1 C7 H7 109.0 . . ?
C8 C7 H7 109.0 . . ?
N1 C8 C7 110.3(3) . . ?
N1 C8 H8A 109.6 . . ?
C7 C8 H8A 109.6 . . ?
N1 C8 H8B 109.6 . . ?
C7 C8 H8B 109.6 . . ?
H8A C8 H8B 108.1 . . ?
N2 C9 N1 109.6(3) . . ?
N2 C9 H9 125.2 . . ?
N1 C9 H9 125.2 . . ?
C11 C10 N2 107.3(4) . . ?
C11 C10 H10 126.3 . . ?
N2 C10 H10 126.3 . . ?
C10 C11 N1 107.6(4) . . ?
C10 C11 H11 126.2 . . ?
N1 C11 H11 126.2 . . ?
O1 C12 C14 106.1(3) . . ?
O1 C12 H12A 110.5 . . ?
C14 C12 H12A 110.5 . . ?
O1 C12 H12B 110.5 . . ?
C14 C12 H12B 110.5 . . ?
H12A C12 H12B 108.7 . . ?
C14 C13 S2 113.8(4) . . ?
C14 C13 Cl3 126.0(4) . . ?
S2 C13 Cl3 120.1(3) . . ?
C13 C14 C15 109.8(4) . . ?
C13 C14 C12 126.6(4) . . ?
C15 C14 C12 123.5(4) . . ?
C16 C15 C14 112.9(5) . . ?
C16 C15 H15 123.5 . . ?
C14 C15 H15 123.5 . . ?
C15 C16 S2 113.2(4) . . ?
C15 C16 H16 123.4 . . ?
S2 C16 H16 123.4 . . ?
O2 C17 O3 127.1(3) . . ?
O2 C17 C17 120.6(4) . 2_766 ?
O3 C17 C17 112.3(3) . 2_766 ?
O5 C18 O4 126.3(3) . . ?
O5 C18 C18 120.0(4) . 2_767 ?
O4 C18 C18 113.7(3) . 2_767 ?
C9 N1 C11 107.2(3) . . ?
C9 N1 C8 127.5(3) . . ?
C11 N1 C8 125.2(3) . . ?
C9 N2 C10 108.4(3) . . ?
C9 N2 H2N 124(5) . . ?
C10 N2 H2N 127(5) . . ?
C7 O1 C12 114.6(3) . . ?
C17 O3 H3O 107(5) . . ?
C16 S2 C13 90.2(3) . . ?

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
C6 C1 C2 C3 0.9(6) . . . . ?
C7 C1 C2 C3 -179.3(4) . . . . ?
C6 C1 C2 Cl1 -179.1(3) . . . . ?
C7 C1 C2 Cl1 0.7(6) . . . . ?
C1 C2 C3 C4 -2.0(7) . . . . ?
Cl1 C2 C3 C4 178.0(4) . . . . ?
C2 C3 C4 C5 1.8(8) . . . . ?
C2 C3 C4 Cl2 -177.7(4) . . . . ?
C3 C4 C5 C6 -0.5(7) . . . . ?
Cl2 C4 C5 C6 178.9(4) . . . . ?
C2 C1 C6 C5 0.4(6) . . . . ?
C7 C1 C6 C5 -179.4(4) . . . . ?
C4 C5 C6 C1 -0.7(7) . . . . ?
C6 C1 C7 O1 12.4(5) . . . . ?
C2 C1 C7 O1 -167.4(3) . . . . ?
C6 C1 C7 C8 -105.9(4) . . . . ?
C2 C1 C7 C8 74.3(5) . . . . ?
O1 C7 C8 N1 71.1(3) . . . . ?
C1 C7 C8 N1 -166.3(3) . . . . ?
N2 C10 C11 N1 -0.2(6) . . . . ?
S2 C13 C14 C15 0.2(5) . . . . ?
Cl3 C13 C14 C15 -179.6(4) . . . . ?
S2 C13 C14 C12 -175.9(3) . . . . ?
Cl3 C13 C14 C12 4.2(8) . . . . ?
O1 C12 C14 C13 98.4(5) . . . . ?
O1 C12 C14 C15 -77.2(5) . . . . ?
C13 C14 C15 C16 -0.1(6) . . . . ?
C12 C14 C15 C16 176.2(4) . . . . ?
C14 C15 C16 S2 -0.1(6) . . . . ?
N2 C9 N1 C11 -0.1(5) . . . . ?
N2 C9 N1 C8 175.6(3) . . . . ?
C10 C11 N1 C9 0.2(6) . . . . ?
C10 C11 N1 C8 -175.7(4) . . . . ?
C7 C8 N1 C9 -82.5(5) . . . . ?
C7 C8 N1 C11 92.6(5) . . . . ?
N1 C9 N2 C10 0.0(5) . . . . ?
C11 C10 N2 C9 0.1(6) . . . . ?
C1 C7 O1 C12 79.4(4) . . . . ?
C8 C7 O1 C12 -158.2(3) . . . . ?
C14 C12 O1 C7 -176.1(3) . . . . ?
C15 C16 S2 C13 0.2(4) . . . . ?
C14 C13 S2 C16 -0.3(4) . . . . ?
Cl3 C13 S2 C16 179.6(4) . . . . ?

_refine_diff_density_max         0.930
_refine_diff_density_min         -0.669
_refine_diff_density_rms         0.119

####################################################################### 
# 
# 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_TCZ_NICA
_database_code_depnum_ccdc_archive 'CCDC 2285612'
loop_
_audit_author_name
_audit_author_address
'Tejender Thakur'
;CSIR Central Drug Research Institute
India
;
_audit_update_record             
;
2023-07-31 deposited with the CCDC.	2023-11-14 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT230_TCZ_NICA            
;
PROBLEM: Hirshfeld Test Diff for    S2       --C32      .       10.0 s.u.
RESPONSE: Elongated thermal ellipsoids were observed for S2 and C32 indicating positional disporder but could not be resolved as refinment was not stable
;
_vrf_PLAT355_TCZ_NICA            
;
PROBLEM: Long   O-H (X0.82,N0.98A)  O5       - H5A      .       1.10 Ang.
RESPONSE: elongated O-H may be attributed to partial transfer of acid proton to imidazole group of drug
;
# Added during the CSD deposition process: Monday 31 July 2023 10:31 AM
# end Validation Reply Form


_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            'Tioconazole-Nicotinic acid cocrystal'
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H13 Cl3 N2 O S, C6 H5 N O2'
_chemical_formula_sum            'C22 H18 Cl3 N3 O3 S'
_chemical_formula_weight         510.80

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'
Cl Cl 0.3639 0.7018 '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                   8.0219(2)
_cell_length_b                   12.3226(3)
_cell_length_c                   23.9838(5)
_cell_angle_alpha                97.644(2)
_cell_angle_beta                 99.212(2)
_cell_angle_gamma                90.462(2)
_cell_volume                     2318.40(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    30291
_cell_measurement_theta_min      3.6060
_cell_measurement_theta_max      72.5670

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.463
_exptl_crystal_F_000             1048
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.870
_exptl_crystal_size_mid          0.380
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    4.677
_shelx_estimated_absorpt_T_min   0.106
_shelx_estimated_absorpt_T_max   0.604
_exptl_absorpt_correction_T_min  0.13435
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_source_power             0.0
_diffrn_source_voltage           50.0
_diffrn_source_current           0.6
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   MicroMax003_Cu
_diffrn_radiation_monochromator  Confocal
_diffrn_measurement_specimen_support Loop
_diffrn_detector                 CCD
_diffrn_measurement_device       
;
AFC12 (Right): Kappa 3 circle
;
_diffrn_measurement_device_type  
;
Rigaku Saturn724+ (4x4 bin mode)
;
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_reflns_number            48662
_diffrn_reflns_av_unetI/netI     0.0693
_diffrn_reflns_av_R_equivalents  0.1407
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         3.621
_diffrn_reflns_theta_max         72.776
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.960
_diffrn_measured_fraction_theta_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.960
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.960
_diffrn_reflns_point_group_measured_fraction_full 0.983
_reflns_number_total             8855
_reflns_number_gt                7791
_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       'CrystalClear-SM Expert 2.1 b28 (Rigaku, 2013)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_structure_solution    'SIR-2011 (Burla et al., 2012)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'
_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)+(0.1318P)²+0.5409P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   direct
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.0122(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         8855
_refine_ls_number_parameters     582
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0813
_refine_ls_R_factor_gt           0.0730
_refine_ls_wR_factor_ref         0.2019
_refine_ls_wR_factor_gt          0.1879
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_restrained_S_all      1.086
_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
C1 C 0.7394(3) 0.62138(19) 0.31824(10) 0.0428(5) Uani 1 1 d . . . . .
C2 C 0.6629(3) 0.72309(19) 0.31855(10) 0.0445(5) Uani 1 1 d . . . . .
C3 C 0.6957(3) 0.8047(2) 0.36434(11) 0.0502(6) Uani 1 1 d . . . . .
H3 H 0.643463 0.871717 0.363391 0.060 Uiso 1 1 calc R U . . .
C4 C 0.8085(3) 0.7850(2) 0.41194(11) 0.0523(6) Uani 1 1 d . . . . .
C5 C 0.8882(3) 0.6866(2) 0.41329(11) 0.0522(6) Uani 1 1 d . . . . .
H5 H 0.964216 0.674326 0.445249 0.063 Uiso 1 1 calc R U . . .
C6 C 0.8540(3) 0.6063(2) 0.36675(10) 0.0469(5) Uani 1 1 d . . . . .
H6 H 0.908836 0.540251 0.367702 0.056 Uiso 1 1 calc R U . . .
C7 C 0.6979(3) 0.53000(18) 0.26897(10) 0.0425(5) Uani 1 1 d . . . . .
H7 H 0.575689 0.526951 0.255705 0.051 Uiso 1 1 calc R U . . .
C8 C 0.7884(3) 0.5468(2) 0.21908(10) 0.0482(5) Uani 1 1 d . . . . .
H8A H 0.779859 0.622501 0.212095 0.058 Uiso 1 1 calc R U . . .
H8B H 0.907207 0.531416 0.228602 0.058 Uiso 1 1 calc R U . . .
C9 C 0.7345(4) 0.3668(2) 0.15585(12) 0.0646(7) Uani 1 1 d . . . . .
H9 H 0.810264 0.326749 0.177923 0.078 Uiso 1 1 calc R U . . .
C10 C 0.5452(4) 0.4098(3) 0.08993(14) 0.0710(8) Uani 1 1 d . . . . .
H10 H 0.464165 0.404606 0.057205 0.085 Uiso 1 1 calc R U . . .
C11 C 0.5919(4) 0.5024(2) 0.12587(13) 0.0636(7) Uani 1 1 d . . . . .
H11 H 0.549755 0.571779 0.122708 0.076 Uiso 1 1 calc R U . . .
O1 O 0.7482(2) 0.42648(13) 0.28479(7) 0.0442(4) Uani 1 1 d . . . . .
C13 C 0.7562(3) 0.2672(2) 0.38872(11) 0.0523(6) Uani 1 1 d . . . . .
C14 C 0.6967(3) 0.2760(2) 0.33347(10) 0.0443(5) Uani 1 1 d . . . . .
C15 C 0.7075(3) 0.1747(2) 0.29874(12) 0.0533(6) Uani 1 1 d . . . . .
H15 H 0.673900 0.164020 0.259407 0.064 Uiso 1 1 calc R U . . .
C16 C 0.7722(4) 0.0950(2) 0.32906(15) 0.0655(8) Uani 1 1 d . . . . .
H16 H 0.786696 0.023671 0.312737 0.079 Uiso 1 1 calc R U . . .
C17 C 0.2295(3) 0.02861(18) 0.31505(10) 0.0419(5) Uani 1 1 d . . . . .
C18 C 0.1501(3) -0.07360(18) 0.31312(10) 0.0425(5) Uani 1 1 d . . . . .
C19 C 0.1834(3) -0.13568(19) 0.35740(11) 0.0488(6) Uani 1 1 d . . . . .
H19 H 0.128593 -0.203207 0.355390 0.059 Uiso 1 1 calc R U . . .
C20 C 0.2991(3) -0.0956(2) 0.40434(11) 0.0512(6) Uani 1 1 d . . . . .
C21 C 0.3826(3) 0.0047(2) 0.40785(11) 0.0524(6) Uani 1 1 d . . . . .
H21 H 0.460970 0.030942 0.439834 0.063 Uiso 1 1 calc R U . . .
C22 C 0.3473(3) 0.0644(2) 0.36320(10) 0.0475(5) Uani 1 1 d . . . . .
H22 H 0.404342 0.131239 0.365259 0.057 Uiso 1 1 calc R U . . .
C23 C 0.1889(3) 0.09777(18) 0.26689(10) 0.0430(5) Uani 1 1 d . . . . .
H23 H 0.066547 0.094719 0.253777 0.052 Uiso 1 1 calc R U . . .
C24 C 0.2780(3) 0.0577(2) 0.21701(10) 0.0477(5) Uani 1 1 d . . . . .
H24A H 0.397288 0.077898 0.226832 0.057 Uiso 1 1 calc R U . . .
H24B H 0.267353 -0.021487 0.208983 0.057 Uiso 1 1 calc R U . . .
C25 C 0.2272(5) 0.2084(2) 0.15603(13) 0.0678(8) Uani 1 1 d . . . . .
H25 H 0.302709 0.259641 0.179093 0.081 Uiso 1 1 calc R U . . .
C26 C 0.0409(4) 0.1325(3) 0.08817(14) 0.0692(8) Uani 1 1 d . . . . .
H26 H -0.037893 0.121149 0.054842 0.083 Uiso 1 1 calc R U . . .
C27 C 0.0857(4) 0.0572(2) 0.12345(13) 0.0611(7) Uani 1 1 d . . . . .
H27 H 0.043105 -0.014341 0.119134 0.073 Uiso 1 1 calc R U . . .
C28 C 0.1249(3) 0.2720(2) 0.31378(13) 0.0538(6) Uani 1 1 d . . . . .
H28A H 0.093998 0.234069 0.343724 0.065 Uiso 1 1 calc R U . . .
H28B H 0.023341 0.280780 0.286975 0.065 Uiso 1 1 calc R U . . .
C29 C 0.2637(4) 0.4111(2) 0.39468(12) 0.0583(6) Uani 1 1 d . . . . .
C30 C 0.2024(3) 0.3812(2) 0.33868(11) 0.0463(5) Uani 1 1 d . . . . .
C31 C 0.2200(3) 0.4697(2) 0.30741(13) 0.0557(6) Uani 1 1 d . . . . .
H31 H 0.186846 0.465701 0.268199 0.067 Uiso 1 1 calc R U . . .
C32 C 0.2910(4) 0.5611(2) 0.34143(17) 0.0728(9) Uani 1 1 d . . . . .
H32 H 0.310461 0.626619 0.327915 0.087 Uiso 1 1 calc R U . . .
C33 C 0.1744(3) 0.6048(2) 0.09850(11) 0.0508(6) Uani 1 1 d . . . . .
C37 C 0.1924(4) 0.6152(2) 0.04316(12) 0.0630(7) Uani 1 1 d . . . . .
H37 H 0.179091 0.554436 0.015136 0.076 Uiso 1 1 calc R U . . .
C35 C 0.2457(5) 0.8045(3) 0.07240(17) 0.0797(9) Uani 1 1 d . . . . .
H35 H 0.272198 0.872922 0.063236 0.096 Uiso 1 1 calc R U . . .
N5 N 0.2251(4) 0.7979(2) 0.12577(14) 0.0811(8) Uani 1 1 d . . . . .
C34 C 0.1909(4) 0.6986(3) 0.13746(13) 0.0652(7) Uani 1 1 d . . . . .
H34 H 0.177054 0.691887 0.174629 0.078 Uiso 1 1 calc R U . . .
C38 C 0.1416(4) 0.4965(2) 0.11682(11) 0.0559(6) Uani 1 1 d . . . . .
C39 C 0.6694(3) -0.0585(2) 0.09556(11) 0.0515(6) Uani 1 1 d . . . . .
C40 C 0.6808(4) -0.1311(3) 0.13524(13) 0.0645(7) Uani 1 1 d . . . . .
H40 H 0.661207 -0.104773 0.171715 0.077 Uiso 1 1 calc R U . . .
C41 C 0.7458(5) -0.2710(3) 0.07214(18) 0.0807(10) Uani 1 1 d . . . . .
H41 H 0.774885 -0.343582 0.063957 0.097 Uiso 1 1 calc R U . . .
C42 C 0.7343(5) -0.2062(3) 0.02892(15) 0.0769(9) Uani 1 1 d . . . . .
H42 H 0.752303 -0.234779 -0.007441 0.092 Uiso 1 1 calc R U . . .
C43 C 0.6954(4) -0.0983(2) 0.04136(12) 0.0635(7) Uani 1 1 d . . . . .
H43 H 0.686601 -0.052343 0.013306 0.076 Uiso 1 1 calc R U . . .
C44 C 0.6360(4) 0.0592(2) 0.11350(11) 0.0569(6) Uani 1 1 d . . . . .
N1 N 0.7132(3) 0.47459(16) 0.16777(9) 0.0485(5) Uani 1 1 d . . . . .
N2 N 0.6345(4) 0.3251(2) 0.10885(11) 0.0674(7) Uani 1 1 d . . . . .
N3 N 0.2048(3) 0.10570(16) 0.16639(9) 0.0484(5) Uani 1 1 d . . . . .
N4 N 0.1295(4) 0.2279(2) 0.10927(11) 0.0688(7) Uani 1 1 d . . . . .
C36 C 0.2306(5) 0.7174(3) 0.03023(15) 0.0734(9) Uani 1 1 d . . . . .
H36 H 0.245651 0.726647 -0.006513 0.088 Uiso 1 1 calc R U . . .
N6 N 0.7180(4) -0.2362(2) 0.12466(13) 0.0807(8) Uani 1 1 d . . . . .
C12 C 0.6257(3) 0.3775(2) 0.31211(11) 0.0485(5) Uani 1 1 d . . . . .
H12A H 0.522364 0.359310 0.285201 0.058 Uiso 1 1 calc R U . . .
H12B H 0.599337 0.428649 0.343669 0.058 Uiso 1 1 calc R U . . .
O2 O 0.24384(19) 0.20935(12) 0.28513(7) 0.0443(4) Uani 1 1 d . . . . .
O3 O 0.1473(4) 0.4867(2) 0.16699(9) 0.0816(7) Uani 1 1 d . . . . .
O4 O 0.1142(3) 0.41644(17) 0.07517(9) 0.0742(6) Uani 1 1 d . . . . .
H4 H 0.126(6) 0.348(4) 0.0901(8) 0.111 Uiso 1 1 calc R U . . .
O5 O 0.6165(3) 0.11860(18) 0.07214(9) 0.0730(6) Uani 1 1 d . . . . .
H5A H 0.620(6) 0.206(4) 0.0899(8) 0.109 Uiso 1 1 calc R U . . .
O6 O 0.6320(4) 0.0946(2) 0.16271(10) 0.0915(8) Uani 1 1 d . . . . .
S1 S 0.82361(10) 0.13904(7) 0.39972(4) 0.0697(3) Uani 1 1 d . . . . .
S2 S 0.34004(11) 0.54320(7) 0.41076(4) 0.0770(3) Uani 1 1 d . . . . .
Cl1 Cl 0.51980(9) 0.75006(6) 0.25960(3) 0.0624(2) Uani 1 1 d . . . . .
Cl2 Cl 0.84810(13) 0.88740(7) 0.46979(4) 0.0809(3) Uani 1 1 d . . . . .
Cl3 Cl 0.76918(13) 0.36898(8) 0.44596(3) 0.0846(3) Uani 1 1 d . . . . .
Cl4 Cl 0.00371(9) -0.12720(5) 0.25375(3) 0.0590(2) Uani 1 1 d . . . . .
Cl5 Cl 0.34267(12) -0.17328(7) 0.45987(3) 0.0758(3) Uani 1 1 d . . . . .
Cl6 Cl 0.26962(15) 0.33117(10) 0.44868(4) 0.0976(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
C1 C6 1.397(3) . ?
C1 C2 1.399(3) . ?
C1 C7 1.513(3) . ?
C2 C3 1.377(4) . ?
C2 Cl1 1.743(2) . ?
C3 C4 1.388(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.377(4) . ?
C4 Cl2 1.734(3) . ?
C5 C6 1.379(4) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 O1 1.422(3) . ?
C7 C8 1.531(3) . ?
C7 H7 0.9800 . ?
C8 N1 1.461(3) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 N2 1.315(4) . ?
C9 N1 1.339(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.347(4) . ?
C10 N2 1.357(4) . ?
C10 H10 0.9300 . ?
C11 N1 1.363(4) . ?
C11 H11 0.9300 . ?
O1 C12 1.436(3) . ?
C13 C14 1.353(4) . ?
C13 S1 1.713(3) . ?
C13 Cl3 1.721(3) . ?
C14 C15 1.417(4) . ?
C14 C12 1.497(3) . ?
C15 C16 1.356(4) . ?
C15 H15 0.9300 . ?
C16 S1 1.692(4) . ?
C16 H16 0.9300 . ?
C17 C22 1.389(3) . ?
C17 C18 1.399(3) . ?
C17 C23 1.521(3) . ?
C18 C19 1.383(3) . ?
C18 Cl4 1.745(2) . ?
C19 C20 1.372(4) . ?
C19 H19 0.9300 . ?
C20 C21 1.387(4) . ?
C20 Cl5 1.734(3) . ?
C21 C22 1.373(4) . ?
C21 H21 0.9300 . ?
C22 H22 0.9300 . ?
C23 O2 1.430(3) . ?
C23 C24 1.520(3) . ?
C23 H23 0.9800 . ?
C24 N3 1.461(3) . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C25 N4 1.313(4) . ?
C25 N3 1.338(3) . ?
C25 H25 0.9300 . ?
C26 C27 1.350(4) . ?
C26 N4 1.362(4) . ?
C26 H26 0.9300 . ?
C27 N3 1.357(4) . ?
C27 H27 0.9300 . ?
C28 O2 1.435(3) . ?
C28 C30 1.486(3) . ?
C28 H28A 0.9700 . ?
C28 H28B 0.9700 . ?
C29 C30 1.355(4) . ?
C29 S2 1.708(3) . ?
C29 Cl6 1.723(3) . ?
C30 C31 1.422(4) . ?
C31 C32 1.362(4) . ?
C31 H31 0.9300 . ?
C32 S2 1.691(4) . ?
C32 H32 0.9300 . ?
C33 C34 1.377(4) . ?
C33 C37 1.380(4) . ?
C33 C38 1.494(4) . ?
C37 C36 1.380(4) . ?
C37 H37 0.9300 . ?
C35 N5 1.329(5) . ?
C35 C36 1.364(5) . ?
C35 H35 0.9300 . ?
N5 C34 1.328(4) . ?
C34 H34 0.9300 . ?
C38 O3 1.219(3) . ?
C38 O4 1.297(3) . ?
C39 C43 1.376(4) . ?
C39 C40 1.383(4) . ?
C39 C44 1.496(4) . ?
C40 N6 1.331(4) . ?
C40 H40 0.9300 . ?
C41 N6 1.330(5) . ?
C41 C42 1.383(5) . ?
C41 H41 0.9300 . ?
C42 C43 1.373(5) . ?
C42 H42 0.9300 . ?
C43 H43 0.9300 . ?
C44 O6 1.208(3) . ?
C44 O5 1.300(3) . ?
C36 H36 0.9300 . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
O4 H4 0.96(5) . ?
O5 H5A 1.10(5) . ?

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
C6 C1 C2 116.7(2) . . ?
C6 C1 C7 120.8(2) . . ?
C2 C1 C7 122.5(2) . . ?
C3 C2 C1 122.4(2) . . ?
C3 C2 Cl1 117.53(19) . . ?
C1 C2 Cl1 120.03(19) . . ?
C2 C3 C4 118.6(2) . . ?
C2 C3 H3 120.7 . . ?
C4 C3 H3 120.7 . . ?
C5 C4 C3 121.0(2) . . ?
C5 C4 Cl2 120.5(2) . . ?
C3 C4 Cl2 118.5(2) . . ?
C4 C5 C6 119.3(2) . . ?
C4 C5 H5 120.3 . . ?
C6 C5 H5 120.3 . . ?
C5 C6 C1 122.0(2) . . ?
C5 C6 H6 119.0 . . ?
C1 C6 H6 119.0 . . ?
O1 C7 C1 112.03(18) . . ?
O1 C7 C8 105.98(18) . . ?
C1 C7 C8 112.13(18) . . ?
O1 C7 H7 108.9 . . ?
C1 C7 H7 108.9 . . ?
C8 C7 H7 108.9 . . ?
N1 C8 C7 110.28(19) . . ?
N1 C8 H8A 109.6 . . ?
C7 C8 H8A 109.6 . . ?
N1 C8 H8B 109.6 . . ?
C7 C8 H8B 109.6 . . ?
H8A C8 H8B 108.1 . . ?
N2 C9 N1 111.2(3) . . ?
N2 C9 H9 124.4 . . ?
N1 C9 H9 124.4 . . ?
C11 C10 N2 109.5(3) . . ?
C11 C10 H10 125.3 . . ?
N2 C10 H10 125.3 . . ?
C10 C11 N1 106.6(3) . . ?
C10 C11 H11 126.7 . . ?
N1 C11 H11 126.7 . . ?
C7 O1 C12 112.22(17) . . ?
C14 C13 S1 113.7(2) . . ?
C14 C13 Cl3 127.0(2) . . ?
S1 C13 Cl3 119.35(15) . . ?
C13 C14 C15 110.4(2) . . ?
C13 C14 C12 124.9(2) . . ?
C15 C14 C12 124.7(2) . . ?
C16 C15 C14 112.7(3) . . ?
C16 C15 H15 123.7 . . ?
C14 C15 H15 123.7 . . ?
C15 C16 S1 113.0(2) . . ?
C15 C16 H16 123.5 . . ?
S1 C16 H16 123.5 . . ?
C22 C17 C18 116.9(2) . . ?
C22 C17 C23 121.3(2) . . ?
C18 C17 C23 121.8(2) . . ?
C19 C18 C17 122.0(2) . . ?
C19 C18 Cl4 117.59(17) . . ?
C17 C18 Cl4 120.37(18) . . ?
C20 C19 C18 118.6(2) . . ?
C20 C19 H19 120.7 . . ?
C18 C19 H19 120.7 . . ?
C19 C20 C21 121.4(2) . . ?
C19 C20 Cl5 118.95(19) . . ?
C21 C20 Cl5 119.7(2) . . ?
C22 C21 C20 118.7(2) . . ?
C22 C21 H21 120.6 . . ?
C20 C21 H21 120.6 . . ?
C21 C22 C17 122.3(2) . . ?
C21 C22 H22 118.9 . . ?
C17 C22 H22 118.9 . . ?
O2 C23 C24 106.32(17) . . ?
O2 C23 C17 111.28(18) . . ?
C24 C23 C17 111.63(19) . . ?
O2 C23 H23 109.2 . . ?
C24 C23 H23 109.2 . . ?
C17 C23 H23 109.2 . . ?
N3 C24 C23 110.5(2) . . ?
N3 C24 H24A 109.6 . . ?
C23 C24 H24A 109.6 . . ?
N3 C24 H24B 109.6 . . ?
C23 C24 H24B 109.6 . . ?
H24A C24 H24B 108.1 . . ?
N4 C25 N3 111.6(3) . . ?
N4 C25 H25 124.2 . . ?
N3 C25 H25 124.2 . . ?
C27 C26 N4 109.0(3) . . ?
C27 C26 H26 125.5 . . ?
N4 C26 H26 125.5 . . ?
C26 C27 N3 107.1(2) . . ?
C26 C27 H27 126.5 . . ?
N3 C27 H27 126.5 . . ?
O2 C28 C30 109.21(19) . . ?
O2 C28 H28A 109.8 . . ?
C30 C28 H28A 109.8 . . ?
O2 C28 H28B 109.8 . . ?
C30 C28 H28B 109.8 . . ?
H28A C28 H28B 108.3 . . ?
C30 C29 S2 113.9(2) . . ?
C30 C29 Cl6 127.0(2) . . ?
S2 C29 Cl6 119.08(18) . . ?
C29 C30 C31 110.4(2) . . ?
C29 C30 C28 124.7(2) . . ?
C31 C30 C28 124.9(3) . . ?
C32 C31 C30 112.3(3) . . ?
C32 C31 H31 123.9 . . ?
C30 C31 H31 123.9 . . ?
C31 C32 S2 113.1(2) . . ?
C31 C32 H32 123.5 . . ?
S2 C32 H32 123.5 . . ?
C34 C33 C37 117.6(3) . . ?
C34 C33 C38 120.2(2) . . ?
C37 C33 C38 122.2(2) . . ?
C36 C37 C33 118.7(3) . . ?
C36 C37 H37 120.7 . . ?
C33 C37 H37 120.7 . . ?
N5 C35 C36 124.2(3) . . ?
N5 C35 H35 117.9 . . ?
C36 C35 H35 117.9 . . ?
C34 N5 C35 116.1(3) . . ?
N5 C34 C33 124.7(3) . . ?
N5 C34 H34 117.7 . . ?
C33 C34 H34 117.7 . . ?
O3 C38 O4 124.8(3) . . ?
O3 C38 C33 121.3(3) . . ?
O4 C38 C33 113.9(2) . . ?
C43 C39 C40 117.7(3) . . ?
C43 C39 C44 123.0(2) . . ?
C40 C39 C44 119.3(2) . . ?
N6 C40 C39 124.3(3) . . ?
N6 C40 H40 117.8 . . ?
C39 C40 H40 117.8 . . ?
N6 C41 C42 124.2(3) . . ?
N6 C41 H41 117.9 . . ?
C42 C41 H41 117.9 . . ?
C43 C42 C41 117.9(3) . . ?
C43 C42 H42 121.1 . . ?
C41 C42 H42 121.1 . . ?
C42 C43 C39 119.6(3) . . ?
C42 C43 H43 120.2 . . ?
C39 C43 H43 120.2 . . ?
O6 C44 O5 124.0(3) . . ?
O6 C44 C39 121.8(3) . . ?
O5 C44 C39 114.2(2) . . ?
C9 N1 C11 106.8(2) . . ?
C9 N1 C8 127.1(2) . . ?
C11 N1 C8 125.7(2) . . ?
C9 N2 C10 106.0(2) . . ?
C25 N3 C27 106.5(2) . . ?
C25 N3 C24 127.3(2) . . ?
C27 N3 C24 125.9(2) . . ?
C25 N4 C26 105.8(2) . . ?
C35 C36 C37 118.7(3) . . ?
C35 C36 H36 120.7 . . ?
C37 C36 H36 120.7 . . ?
C41 N6 C40 116.2(3) . . ?
O1 C12 C14 108.84(18) . . ?
O1 C12 H12A 109.9 . . ?
C14 C12 H12A 109.9 . . ?
O1 C12 H12B 109.9 . . ?
C14 C12 H12B 109.9 . . ?
H12A C12 H12B 108.3 . . ?
C23 O2 C28 112.87(17) . . ?
C38 O4 H4 109.5 . . ?
C44 O5 H5A 109.5 . . ?
C16 S1 C13 90.21(14) . . ?
C32 S2 C29 90.34(15) . . ?

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
C6 C1 C2 C3 -0.9(3) . . . . ?
C7 C1 C2 C3 177.4(2) . . . . ?
C6 C1 C2 Cl1 179.33(17) . . . . ?
C7 C1 C2 Cl1 -2.4(3) . . . . ?
C1 C2 C3 C4 -0.2(4) . . . . ?
Cl1 C2 C3 C4 179.60(19) . . . . ?
C2 C3 C4 C5 0.9(4) . . . . ?
C2 C3 C4 Cl2 -179.41(19) . . . . ?
C3 C4 C5 C6 -0.6(4) . . . . ?
Cl2 C4 C5 C6 179.81(19) . . . . ?
C4 C5 C6 C1 -0.6(4) . . . . ?
C2 C1 C6 C5 1.3(3) . . . . ?
C7 C1 C6 C5 -177.0(2) . . . . ?
C6 C1 C7 O1 16.4(3) . . . . ?
C2 C1 C7 O1 -161.8(2) . . . . ?
C6 C1 C7 C8 -102.6(2) . . . . ?
C2 C1 C7 C8 79.2(3) . . . . ?
O1 C7 C8 N1 72.2(2) . . . . ?
C1 C7 C8 N1 -165.3(2) . . . . ?
N2 C10 C11 N1 0.2(4) . . . . ?
C1 C7 O1 C12 82.8(2) . . . . ?
C8 C7 O1 C12 -154.63(19) . . . . ?
S1 C13 C14 C15 -0.4(3) . . . . ?
Cl3 C13 C14 C15 179.55(19) . . . . ?
S1 C13 C14 C12 178.27(18) . . . . ?
Cl3 C13 C14 C12 -1.8(4) . . . . ?
C13 C14 C15 C16 0.6(3) . . . . ?
C12 C14 C15 C16 -178.1(2) . . . . ?
C14 C15 C16 S1 -0.6(3) . . . . ?
C22 C17 C18 C19 1.5(3) . . . . ?
C23 C17 C18 C19 -178.4(2) . . . . ?
C22 C17 C18 Cl4 -178.53(17) . . . . ?
C23 C17 C18 Cl4 1.6(3) . . . . ?
C17 C18 C19 C20 -0.5(4) . . . . ?
Cl4 C18 C19 C20 179.50(19) . . . . ?
C18 C19 C20 C21 -0.4(4) . . . . ?
C18 C19 C20 Cl5 -179.58(18) . . . . ?
C19 C20 C21 C22 0.2(4) . . . . ?
Cl5 C20 C21 C22 179.4(2) . . . . ?
C20 C21 C22 C17 0.9(4) . . . . ?
C18 C17 C22 C21 -1.6(4) . . . . ?
C23 C17 C22 C21 178.2(2) . . . . ?
C22 C17 C23 O2 -17.5(3) . . . . ?
C18 C17 C23 O2 162.3(2) . . . . ?
C22 C17 C23 C24 101.1(3) . . . . ?
C18 C17 C23 C24 -79.1(3) . . . . ?
O2 C23 C24 N3 -73.1(2) . . . . ?
C17 C23 C24 N3 165.38(18) . . . . ?
N4 C26 C27 N3 -0.8(4) . . . . ?
S2 C29 C30 C31 0.6(3) . . . . ?
Cl6 C29 C30 C31 -179.9(2) . . . . ?
S2 C29 C30 C28 -178.34(19) . . . . ?
Cl6 C29 C30 C28 1.2(4) . . . . ?
O2 C28 C30 C29 -103.5(3) . . . . ?
O2 C28 C30 C31 77.7(3) . . . . ?
C29 C30 C31 C32 -0.8(3) . . . . ?
C28 C30 C31 C32 178.1(2) . . . . ?
C30 C31 C32 S2 0.7(3) . . . . ?
C34 C33 C37 C36 1.9(5) . . . . ?
C38 C33 C37 C36 -176.9(3) . . . . ?
C36 C35 N5 C34 1.3(6) . . . . ?
C35 N5 C34 C33 -0.6(6) . . . . ?
C37 C33 C34 N5 -1.0(5) . . . . ?
C38 C33 C34 N5 177.9(3) . . . . ?
C34 C33 C38 O3 -8.2(5) . . . . ?
C37 C33 C38 O3 170.6(3) . . . . ?
C34 C33 C38 O4 174.3(3) . . . . ?
C37 C33 C38 O4 -6.9(4) . . . . ?
C43 C39 C40 N6 1.2(5) . . . . ?
C44 C39 C40 N6 -176.7(3) . . . . ?
N6 C41 C42 C43 1.6(6) . . . . ?
C41 C42 C43 C39 0.0(5) . . . . ?
C40 C39 C43 C42 -1.3(5) . . . . ?
C44 C39 C43 C42 176.6(3) . . . . ?
C43 C39 C44 O6 -171.7(3) . . . . ?
C40 C39 C44 O6 6.1(5) . . . . ?
C43 C39 C44 O5 6.6(4) . . . . ?
C40 C39 C44 O5 -175.6(3) . . . . ?
N2 C9 N1 C11 0.2(4) . . . . ?
N2 C9 N1 C8 173.3(2) . . . . ?
C10 C11 N1 C9 -0.3(4) . . . . ?
C10 C11 N1 C8 -173.5(3) . . . . ?
C7 C8 N1 C9 -76.1(3) . . . . ?
C7 C8 N1 C11 95.7(3) . . . . ?
N1 C9 N2 C10 -0.1(4) . . . . ?
C11 C10 N2 C9 -0.1(4) . . . . ?
N4 C25 N3 C27 0.1(4) . . . . ?
N4 C25 N3 C24 -173.4(2) . . . . ?
C26 C27 N3 C25 0.4(4) . . . . ?
C26 C27 N3 C24 174.0(3) . . . . ?
C23 C24 N3 C25 75.2(3) . . . . ?
C23 C24 N3 C27 -97.1(3) . . . . ?
N3 C25 N4 C26 -0.6(4) . . . . ?
C27 C26 N4 C25 0.9(4) . . . . ?
N5 C35 C36 C37 -0.4(6) . . . . ?
C33 C37 C36 C35 -1.3(5) . . . . ?
C42 C41 N6 C40 -1.6(6) . . . . ?
C39 C40 N6 C41 0.2(5) . . . . ?
C7 O1 C12 C14 -173.39(19) . . . . ?
C13 C14 C12 O1 104.6(3) . . . . ?
C15 C14 C12 O1 -76.9(3) . . . . ?
C24 C23 O2 C28 155.1(2) . . . . ?
C17 C23 O2 C28 -83.2(2) . . . . ?
C30 C28 O2 C23 171.6(2) . . . . ?
C15 C16 S1 C13 0.3(2) . . . . ?
C14 C13 S1 C16 0.1(2) . . . . ?
Cl3 C13 S1 C16 -179.87(17) . . . . ?
C31 C32 S2 C29 -0.3(2) . . . . ?
C30 C29 S2 C32 -0.2(2) . . . . ?
Cl6 C29 S2 C32 -179.75(19) . . . . ?

_refine_diff_density_max         0.814
_refine_diff_density_min         -0.798
_refine_diff_density_rms         0.147

####################################################################### 
# 
# 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_TCZ-SULF
_database_code_depnum_ccdc_archive 'CCDC 2285615'
loop_
_audit_author_name
_audit_author_address
'Tejender Thakur'
;CSIR Central Drug Research Institute
India
;
_audit_update_record             
;
2023-07-31 deposited with the CCDC.	2023-11-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H14 Cl3 N2 O S, H O4 S'
_chemical_formula_sum            'C16 H15 Cl3 N2 O5 S2'
_chemical_formula_weight         485.77

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'
Cl Cl 0.1484 0.1585 '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        'I 2/a'
_space_group_name_Hall           '-I 2ya'

_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, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z'
'-x+1/2, -y+1/2, -z+1/2'
'x, -y+1/2, z+1/2'

_cell_length_a                   16.9432(10)
_cell_length_b                   6.7811(3)
_cell_length_c                   34.455(2)
_cell_angle_alpha                90
_cell_angle_beta                 98.406(5)
_cell_angle_gamma                90
_cell_volume                     3916.1(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    5705
_cell_measurement_theta_min      2.8640
_cell_measurement_theta_max      31.0520

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.648
_exptl_crystal_F_000             1984
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.340
_exptl_crystal_size_mid          0.230
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    0.714
_shelx_estimated_absorpt_T_min   0.793
_shelx_estimated_absorpt_T_max   0.926
_exptl_absorpt_correction_T_min  0.01338
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_source_power             0.0
_diffrn_source_voltage           50.0
_diffrn_source_current           0.6
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   MicroMax003_Mo
_diffrn_radiation_monochromator  Confocal
_diffrn_measurement_specimen_support Loop
_diffrn_detector                 CCD
_diffrn_measurement_device       
;
AFC12 (Right): Kappa 3 circle
;
_diffrn_measurement_device_type  
;
Rigaku Saturn724+ (4x4 bin mode)
;
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_reflns_number            20473
_diffrn_reflns_av_unetI/netI     0.1014
_diffrn_reflns_av_R_equivalents  0.1256
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_limit_l_max       47
_diffrn_reflns_theta_min         2.390
_diffrn_reflns_theta_max         31.497
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.881
_diffrn_measured_fraction_theta_full 0.979
_diffrn_reflns_Laue_measured_fraction_max 0.881
_diffrn_reflns_Laue_measured_fraction_full 0.979
_diffrn_reflns_point_group_measured_fraction_max 0.881
_diffrn_reflns_point_group_measured_fraction_full 0.979
_reflns_number_total             5730
_reflns_number_gt                3352
_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       'CrystalClear-SM Expert 2.1 b28 (Rigaku, 2013)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_structure_solution    'SHELXS-2013/1 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'
_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)+(0.1837P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   direct
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5730
_refine_ls_number_parameters     258
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1484
_refine_ls_R_factor_gt           0.1013
_refine_ls_wR_factor_ref         0.3134
_refine_ls_wR_factor_gt          0.2524
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_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
C1 C 0.0850(3) -0.1085(6) 0.08700(12) 0.0243(8) Uani 1 1 d . . . . .
C2 C 0.0502(3) -0.2527(7) 0.06160(14) 0.0332(10) Uani 1 1 d . . . . .
C3 C -0.0214(3) -0.2240(6) 0.03712(13) 0.0310(10) Uani 1 1 d . . . . .
H3 H -0.043298 -0.322839 0.020141 0.037 Uiso 1 1 calc R U . . .
C4 C -0.0592(3) -0.0454(7) 0.03864(12) 0.0265(9) Uani 1 1 d . . . . .
C5 C -0.0269(3) 0.1046(7) 0.06356(13) 0.0344(11) Uani 1 1 d . . . . .
H5 H -0.052510 0.225780 0.063825 0.041 Uiso 1 1 calc R U . . .
C6 C 0.0444(3) 0.0698(7) 0.08803(13) 0.0319(10) Uani 1 1 d . . . . .
H6 H 0.065484 0.167470 0.105470 0.038 Uiso 1 1 calc R U . . .
C7 C 0.1620(3) -0.1413(6) 0.11489(11) 0.0251(8) Uani 1 1 d . . . . .
H7 H 0.193788 -0.242137 0.103903 0.030 Uiso 1 1 calc R U . . .
C8 C 0.1429(3) -0.2118(6) 0.15442(12) 0.0285(9) Uani 1 1 d . . . . .
H8A H 0.113599 -0.109308 0.165862 0.034 Uiso 1 1 calc R U . . .
H8B H 0.108815 -0.327169 0.150455 0.034 Uiso 1 1 calc R U . . .
C9 C 0.2439(3) -0.4414(7) 0.18783(13) 0.0296(9) Uani 1 1 d . . . . .
H9 H 0.221470 -0.557246 0.176760 0.035 Uiso 1 1 calc R U . . .
C10 C 0.3257(3) -0.2341(7) 0.22226(13) 0.0320(10) Uani 1 1 d . . . . .
H10 H 0.369220 -0.184820 0.239050 0.038 Uiso 1 1 calc R U . . .
C11 C 0.2650(3) -0.1287(7) 0.20286(13) 0.0321(10) Uani 1 1 d . . . . .
H11 H 0.258649 0.007400 0.203689 0.038 Uiso 1 1 calc R U . . .
C12 C 0.2562(3) 0.0795(7) 0.09259(12) 0.0290(9) Uani 1 1 d . . . . .
H12A H 0.223816 0.143255 0.070604 0.035 Uiso 1 1 calc R U . . .
H12B H 0.278783 -0.039787 0.083214 0.035 Uiso 1 1 calc R U . . .
C13 C 0.3393(3) 0.3948(6) 0.09667(12) 0.0293(9) Uani 1 1 d . . . . .
C14 C 0.3220(3) 0.2163(6) 0.11053(12) 0.0255(9) Uani 1 1 d . . . . .
C15 C 0.3736(3) 0.1698(7) 0.14549(13) 0.0329(10) Uani 1 1 d . . . . .
H15 H 0.370732 0.052373 0.159167 0.039 Uiso 1 1 calc R U . . .
C16 C 0.4276(3) 0.3135(7) 0.15702(12) 0.0312(10) Uani 1 1 d . . . . .
H16 H 0.465559 0.305751 0.179363 0.037 Uiso 1 1 calc R U . . .
N1 N 0.2139(2) -0.2606(5) 0.18154(10) 0.0272(8) Uani 1 1 d . . . . .
N2 N 0.3112(3) -0.4275(6) 0.21251(12) 0.0338(9) Uani 1 1 d . . . . .
O1 O 0.20860(19) 0.0327(4) 0.12241(9) 0.0259(7) Uani 1 1 d . . . . .
O2 O 0.0236(3) 0.0780(5) 0.20632(11) 0.0439(9) Uani 1 1 d . . . . .
H2 H 0.017320 0.022460 0.226776 0.066 Uiso 1 1 calc R U . . .
O3 O 0.0819(2) 0.3495(5) 0.17856(10) 0.0425(9) Uani 1 1 d . . . . .
O4 O 0.1316(2) 0.2552(5) 0.24547(10) 0.0417(9) Uani 1 1 d . . . . .
O5 O 0.0022(2) 0.4041(5) 0.23030(11) 0.0470(10) Uani 1 1 d . . . . .
S1 S 0.41777(8) 0.51114(16) 0.12570(3) 0.0320(3) Uani 1 1 d . . . . .
S2 S 0.06333(7) 0.28451(16) 0.21601(3) 0.0279(3) Uani 1 1 d . . . . .
Cl1 Cl 0.09679(9) -0.47951(19) 0.05914(5) 0.0586(5) Uani 1 1 d . . . . .
Cl2 Cl -0.14871(7) -0.00578(18) 0.00791(3) 0.0365(3) Uani 1 1 d . . . . .
Cl3 Cl 0.29824(8) 0.50738(17) 0.05347(4) 0.0374(3) Uani 1 1 d . . . . .
H2N H 0.331(3) -0.529(7) 0.2228(14) 0.034(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
C1 C2 1.385(6) . ?
C1 C6 1.394(6) . ?
C1 C7 1.520(6) . ?
C2 C3 1.386(6) . ?
C2 Cl1 1.737(5) . ?
C3 C4 1.374(6) . ?
C3 H3 0.9300 . ?
C4 C5 1.391(6) . ?
C4 Cl2 1.739(4) . ?
C5 C6 1.388(6) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 O1 1.422(5) . ?
C7 C8 1.523(6) . ?
C7 H7 0.9800 . ?
C8 N1 1.450(5) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 N2 1.321(6) . ?
C9 N1 1.333(5) . ?
C9 H9 0.9300 . ?
C10 C11 1.348(6) . ?
C10 N2 1.367(6) . ?
C10 H10 0.9300 . ?
C11 N1 1.379(5) . ?
C11 H11 0.9300 . ?
C12 O1 1.432(5) . ?
C12 C14 1.511(6) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.349(6) . ?
C13 Cl3 1.726(4) . ?
C13 S1 1.733(4) . ?
C14 C15 1.417(6) . ?
C15 C16 1.356(6) . ?
C15 H15 0.9300 . ?
C16 S1 1.713(5) . ?
C16 H16 0.9300 . ?
N2 H2N 0.82(5) . ?
O2 S2 1.568(3) . ?
O2 H2 0.8200 . ?
O3 S2 1.441(3) . ?
O4 S2 1.437(3) . ?
O5 S2 1.456(4) . ?

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
C2 C1 C6 117.5(4) . . ?
C2 C1 C7 122.9(4) . . ?
C6 C1 C7 119.5(4) . . ?
C1 C2 C3 122.6(4) . . ?
C1 C2 Cl1 120.1(4) . . ?
C3 C2 Cl1 117.3(3) . . ?
C4 C3 C2 118.1(4) . . ?
C4 C3 H3 120.9 . . ?
C2 C3 H3 120.9 . . ?
C3 C4 C5 121.7(4) . . ?
C3 C4 Cl2 118.8(3) . . ?
C5 C4 Cl2 119.5(4) . . ?
C6 C5 C4 118.7(4) . . ?
C6 C5 H5 120.7 . . ?
C4 C5 H5 120.7 . . ?
C5 C6 C1 121.4(4) . . ?
C5 C6 H6 119.3 . . ?
C1 C6 H6 119.3 . . ?
O1 C7 C1 113.4(3) . . ?
O1 C7 C8 106.4(3) . . ?
C1 C7 C8 109.6(3) . . ?
O1 C7 H7 109.1 . . ?
C1 C7 H7 109.1 . . ?
C8 C7 H7 109.1 . . ?
N1 C8 C7 112.5(4) . . ?
N1 C8 H8A 109.1 . . ?
C7 C8 H8A 109.1 . . ?
N1 C8 H8B 109.1 . . ?
C7 C8 H8B 109.1 . . ?
H8A C8 H8B 107.8 . . ?
N2 C9 N1 108.2(4) . . ?
N2 C9 H9 125.9 . . ?
N1 C9 H9 125.9 . . ?
C11 C10 N2 106.8(4) . . ?
C11 C10 H10 126.6 . . ?
N2 C10 H10 126.6 . . ?
C10 C11 N1 107.1(4) . . ?
C10 C11 H11 126.4 . . ?
N1 C11 H11 126.4 . . ?
O1 C12 C14 107.6(3) . . ?
O1 C12 H12A 110.2 . . ?
C14 C12 H12A 110.2 . . ?
O1 C12 H12B 110.2 . . ?
C14 C12 H12B 110.2 . . ?
H12A C12 H12B 108.5 . . ?
C14 C13 Cl3 128.4(3) . . ?
C14 C13 S1 113.1(3) . . ?
Cl3 C13 S1 118.4(3) . . ?
C13 C14 C15 111.2(4) . . ?
C13 C14 C12 126.2(4) . . ?
C15 C14 C12 122.5(4) . . ?
C16 C15 C14 113.3(4) . . ?
C16 C15 H15 123.4 . . ?
C14 C15 H15 123.4 . . ?
C15 C16 S1 112.3(3) . . ?
C15 C16 H16 123.9 . . ?
S1 C16 H16 123.9 . . ?
C9 N1 C11 108.4(4) . . ?
C9 N1 C8 125.2(4) . . ?
C11 N1 C8 126.3(4) . . ?
C9 N2 C10 109.5(4) . . ?
C9 N2 H2N 118(4) . . ?
C10 N2 H2N 131(4) . . ?
C7 O1 C12 114.1(3) . . ?
S2 O2 H2 109.5 . . ?
C16 S1 C13 90.2(2) . . ?
O4 S2 O3 114.6(2) . . ?
O4 S2 O5 112.1(2) . . ?
O3 S2 O5 113.1(2) . . ?
O4 S2 O2 107.6(2) . . ?
O3 S2 O2 103.0(2) . . ?
O5 S2 O2 105.4(2) . . ?

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
C6 C1 C2 C3 1.4(7) . . . . ?
C7 C1 C2 C3 177.9(4) . . . . ?
C6 C1 C2 Cl1 -179.3(4) . . . . ?
C7 C1 C2 Cl1 -2.8(6) . . . . ?
C1 C2 C3 C4 -0.6(7) . . . . ?
Cl1 C2 C3 C4 -180.0(4) . . . . ?
C2 C3 C4 C5 0.7(7) . . . . ?
C2 C3 C4 Cl2 179.5(4) . . . . ?
C3 C4 C5 C6 -1.5(7) . . . . ?
Cl2 C4 C5 C6 179.6(4) . . . . ?
C4 C5 C6 C1 2.3(7) . . . . ?
C2 C1 C6 C5 -2.2(7) . . . . ?
C7 C1 C6 C5 -178.9(4) . . . . ?
C2 C1 C7 O1 148.8(4) . . . . ?
C6 C1 C7 O1 -34.8(5) . . . . ?
C2 C1 C7 C8 -92.5(5) . . . . ?
C6 C1 C7 C8 84.0(5) . . . . ?
O1 C7 C8 N1 -61.5(4) . . . . ?
C1 C7 C8 N1 175.5(3) . . . . ?
N2 C10 C11 N1 0.2(5) . . . . ?
Cl3 C13 C14 C15 174.9(4) . . . . ?
S1 C13 C14 C15 -0.4(5) . . . . ?
Cl3 C13 C14 C12 -5.9(7) . . . . ?
S1 C13 C14 C12 178.8(4) . . . . ?
O1 C12 C14 C13 -125.7(5) . . . . ?
O1 C12 C14 C15 53.4(6) . . . . ?
C13 C14 C15 C16 0.3(6) . . . . ?
C12 C14 C15 C16 -178.9(4) . . . . ?
C14 C15 C16 S1 -0.1(6) . . . . ?
N2 C9 N1 C11 0.7(5) . . . . ?
N2 C9 N1 C8 176.2(4) . . . . ?
C10 C11 N1 C9 -0.5(5) . . . . ?
C10 C11 N1 C8 -176.0(4) . . . . ?
C7 C8 N1 C9 -96.6(5) . . . . ?
C7 C8 N1 C11 78.2(5) . . . . ?
N1 C9 N2 C10 -0.6(5) . . . . ?
C11 C10 N2 C9 0.2(5) . . . . ?
C1 C7 O1 C12 -81.3(4) . . . . ?
C8 C7 O1 C12 158.1(4) . . . . ?
C14 C12 O1 C7 -159.9(3) . . . . ?
C15 C16 S1 C13 -0.1(4) . . . . ?
C14 C13 S1 C16 0.3(4) . . . . ?
Cl3 C13 S1 C16 -175.5(3) . . . . ?

_refine_diff_density_max         1.036
_refine_diff_density_min         -1.230
_refine_diff_density_rms         0.204

####################################################################### 
# 
# 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_TCZ-TPTH2
_database_code_depnum_ccdc_archive 'CCDC 2285617'
loop_
_audit_author_name
_audit_author_address
'Tejender Thakur'
;CSIR Central Drug Research Institute
India
;
_audit_update_record             
;
2023-07-31 deposited with the CCDC.	2023-11-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            
'Tioconazole-ter-pthalic acid (1:0.5) cocrystal'
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H13 Cl3 N2 O1 S, 0.5(C8 H6 O4)'
_chemical_formula_sum            'C20 H16 Cl3 N2 O3 S'
_chemical_formula_weight         470.76

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'
Cl Cl 0.3639 0.7018 '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                   7.4880(2)
_cell_length_b                   11.3843(4)
_cell_length_c                   13.0280(4)
_cell_angle_alpha                83.111(3)
_cell_angle_beta                 83.102(3)
_cell_angle_gamma                75.116(3)
_cell_volume                     1060.94(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    13081
_cell_measurement_theta_min      3.4120
_cell_measurement_theta_max      72.2920

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.474
_exptl_crystal_F_000             482
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.380
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.240
_exptl_absorpt_coefficient_mu    5.044
_shelx_estimated_absorpt_T_min   0.250
_shelx_estimated_absorpt_T_max   0.377
_exptl_absorpt_correction_T_min  0.49881
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_source_power             0.0
_diffrn_source_voltage           50.0
_diffrn_source_current           0.6
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   MicroMax003_Mo
_diffrn_radiation_monochromator  Confocal
_diffrn_measurement_specimen_support Loop
_diffrn_detector                 CCD
_diffrn_measurement_device       
;
AFC12 (Right): Kappa 3 circle
;
_diffrn_measurement_device_type  
;
Rigaku Saturn724+ (4x4 bin mode)
;
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -130.00 -10.00   1.00    6.00    --  -40.00 -72.00   0.00  120
  2  ω   -130.00 -10.00   1.00    6.00    --  -40.00 -72.00  70.00  120
  3  ω   -130.00 -10.00   1.00    6.00    --  -40.00 -72.00 140.00  120
  4  ω   -130.00 -10.00   1.00    6.00    --  -40.00 -72.00 210.00  120
  5  ω   -130.00 -10.00   1.00    6.00    --  -40.00 -72.00 280.00  120
  6  ω   -130.00  50.00   1.00    6.00    --  -40.00   0.00   0.00  180
  7  ω   -100.00  20.00   1.00    6.00    --  -70.00  72.00   0.00  120
  8  ω   -100.00  20.00   1.00    6.00    --  -70.00  72.00  70.00  120
  9  ω   -100.00  20.00   1.00    6.00    --  -70.00  72.00 140.00  120
 10  ω   -100.00  20.00   1.00    6.00    --  -70.00  72.00 210.00  120
 11  ω   -100.00  20.00   1.00    6.00    --  -70.00  72.00 280.00  120
 12  ω   -160.00  20.00   1.00    6.00    --  -70.00   0.00   0.00  180
 13  ω   -190.00 -70.00   1.00    6.00    -- -100.00 -72.00   0.00  120
 14  ω   -190.00 -70.00   1.00    6.00    -- -100.00 -72.00  70.00  120
 15  ω   -190.00 -70.00   1.00    6.00    -- -100.00 -72.00 140.00  120
 16  ω   -190.00 -70.00   1.00    6.00    -- -100.00 -72.00 210.00  120
 17  ω   -190.00 -70.00   1.00    6.00    -- -100.00 -72.00 280.00  120
 18  ω   -130.00 -10.00   1.00    6.00    -- -100.00  72.00   0.00  120
 19  ω   -130.00 -10.00   1.00    6.00    -- -100.00  72.00  70.00  120
 20  ω   -130.00 -10.00   1.00    6.00    -- -100.00  72.00 140.00  120
 21  ω   -130.00 -10.00   1.00    6.00    -- -100.00  72.00 210.00  120
 22  ω   -130.00 -10.00   1.00    6.00    -- -100.00  72.00 280.00  120
 23  ω   -190.00 -10.00   1.00    6.00    -- -100.00   0.00   0.00  180
;
_diffrn_reflns_number            21968
_diffrn_reflns_av_unetI/netI     0.0546
_diffrn_reflns_av_R_equivalents  0.1180
_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       -15
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.432
_diffrn_reflns_theta_max         72.711
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.960
_diffrn_measured_fraction_theta_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.960
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.960
_diffrn_reflns_point_group_measured_fraction_full 0.982
_reflns_number_total             4055
_reflns_number_gt                3406
_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       'CrystalClear-SM Expert 2.1 b28 (Rigaku, 2013)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_structure_solution    'SHELXS-2013/1 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'
_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)+(0.1192P)²+0.2409P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.0052(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4055
_refine_ls_number_parameters     265
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0758
_refine_ls_R_factor_gt           0.0679
_refine_ls_wR_factor_ref         0.1925
_refine_ls_wR_factor_gt          0.1792
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_restrained_S_all      1.075
_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
C1 C -0.5165(4) 1.2084(2) 0.35422(18) 0.0532(6) Uani 1 1 d . . . . .
C2 C -0.6665(4) 1.1765(3) 0.4127(2) 0.0611(6) Uani 1 1 d . . . . .
C3 C -0.6810(4) 1.1631(3) 0.5203(2) 0.0691(8) Uani 1 1 d . . . . .
H3 H -0.783925 1.142536 0.558083 0.083 Uiso 1 1 calc R U . . .
C4 C -0.5397(5) 1.1811(3) 0.5697(2) 0.0659(7) Uani 1 1 d . . . . .
C5 C -0.3892(5) 1.2137(3) 0.5151(2) 0.0704(8) Uani 1 1 d . . . . .
H5 H -0.294819 1.226083 0.549610 0.084 Uiso 1 1 calc R U . . .
C6 C -0.3795(4) 1.2278(3) 0.4080(2) 0.0629(7) Uani 1 1 d . . . . .
H6 H -0.277990 1.250962 0.370925 0.075 Uiso 1 1 calc R U . . .
C7 C -0.4984(3) 1.2221(2) 0.23617(19) 0.0524(6) Uani 1 1 d . . . . .
H7 H -0.558224 1.165730 0.210373 0.063 Uiso 1 1 calc R U . . .
C8 C -0.5873(4) 1.3523(2) 0.19641(19) 0.0563(6) Uani 1 1 d . . . . .
H8A H -0.710160 1.377249 0.232407 0.068 Uiso 1 1 calc R U . . .
H8B H -0.514148 1.405485 0.212649 0.068 Uiso 1 1 calc R U . . .
C9 C -0.7604(4) 1.4120(3) 0.0383(2) 0.0633(7) Uani 1 1 d . . . . .
H9 H -0.876856 1.437276 0.073927 0.076 Uiso 1 1 calc R U . . .
C10 C -0.5430(4) 1.3706(3) -0.0836(2) 0.0635(7) Uani 1 1 d . . . . .
H10 H -0.480189 1.361527 -0.149333 0.076 Uiso 1 1 calc R U . . .
C11 C -0.4626(4) 1.3415(2) 0.0062(2) 0.0592(6) Uani 1 1 d . . . . .
H11 H -0.336924 1.309991 0.013786 0.071 Uiso 1 1 calc R U . . .
C12 C -0.2153(4) 1.0737(2) 0.2023(2) 0.0614(7) Uani 1 1 d . . . . .
H12A H -0.284487 1.027681 0.171649 0.074 Uiso 1 1 calc R U . . .
H12B H -0.204951 1.042343 0.274514 0.074 Uiso 1 1 calc R U . . .
C13 C 0.1021(4) 0.9541(3) 0.1427(2) 0.0622(7) Uani 1 1 d . . . . .
C14 C -0.0265(4) 1.0604(2) 0.14562(19) 0.0541(6) Uani 1 1 d . . . . .
C15 C 0.0395(4) 1.1557(3) 0.0857(2) 0.0647(7) Uani 1 1 d . . . . .
H15 H -0.030409 1.235985 0.078022 0.078 Uiso 1 1 calc R U . . .
C16 C 0.2144(4) 1.1179(3) 0.0409(2) 0.0666(7) Uani 1 1 d . . . . .
H16 H 0.278238 1.169172 -0.000407 0.080 Uiso 1 1 calc R U . . .
C17 C -0.9145(4) 1.4881(3) 0.5907(2) 0.0635(7) Uani 1 1 d . . . . .
C18 C -1.0919(4) 1.4704(3) 0.5946(2) 0.0665(7) Uani 1 1 d . . . . .
H18 H -1.152881 1.450168 0.658136 0.080 Uiso 1 1 calc R U . . .
C19 C -1.1784(5) 1.4827(3) 0.5048(2) 0.0677(7) Uani 1 1 d . . . . .
H19 H -1.297823 1.471728 0.507850 0.081 Uiso 1 1 calc R U . . .
C20 C -0.8165(5) 1.4770(3) 0.6863(2) 0.0691(8) Uani 1 1 d . . . . .
N1 N -0.6031(3) 1.36777(19) 0.08424(15) 0.0534(5) Uani 1 1 d . . . . .
N2 N -0.7298(4) 1.4152(2) -0.06405(18) 0.0675(6) Uani 1 1 d . . . . .
O1 O -0.3088(2) 1.19936(15) 0.19542(13) 0.0557(5) Uani 1 1 d . . . . .
O2 O -0.6583(4) 1.4853(3) 0.68433(18) 0.0891(7) Uani 1 1 d . . . . .
O3 O -0.9220(4) 1.4577(3) 0.77293(17) 0.0864(7) Uani 1 1 d . . . . .
H3A H -0.857(5) 1.449(5) 0.827(3) 0.130 Uiso 1 1 calc R U . . .
S1 S 0.30391(10) 0.96631(7) 0.06896(7) 0.0731(3) Uani 1 1 d . . . . .
Cl1 Cl -0.84653(12) 1.15335(12) 0.35114(7) 0.1011(4) Uani 1 1 d . . . . .
Cl2 Cl -0.55367(17) 1.16338(10) 0.70437(6) 0.0968(4) Uani 1 1 d . . . . .
Cl3 Cl 0.07759(13) 0.81562(8) 0.20149(9) 0.1019(4) 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
C1 C2 1.383(4) . ?
C1 C6 1.385(4) . ?
C1 C7 1.520(3) . ?
C2 C3 1.386(4) . ?
C2 Cl1 1.738(3) . ?
C3 C4 1.372(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.368(4) . ?
C4 Cl2 1.736(3) . ?
C5 C6 1.380(4) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 O1 1.424(3) . ?
C7 C8 1.517(4) . ?
C7 H7 0.9800 . ?
C8 N1 1.466(3) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 N2 1.323(4) . ?
C9 N1 1.338(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.346(4) . ?
C10 N2 1.364(4) . ?
C10 H10 0.9300 . ?
C11 N1 1.373(3) . ?
C11 H11 0.9300 . ?
C12 O1 1.420(3) . ?
C12 C14 1.494(4) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.340(4) . ?
C13 Cl3 1.712(3) . ?
C13 S1 1.718(3) . ?
C14 C15 1.418(4) . ?
C15 C16 1.352(4) . ?
C15 H15 0.9300 . ?
C16 S1 1.696(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.388(4) . ?
C17 C19 1.398(4) 2_386 ?
C17 C20 1.496(4) . ?
C18 C19 1.379(4) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
C20 O2 1.209(4) . ?
C20 O3 1.327(4) . ?
O3 H3A 0.89(5) . ?

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
C2 C1 C6 117.0(2) . . ?
C2 C1 C7 122.7(2) . . ?
C6 C1 C7 120.3(2) . . ?
C1 C2 C3 122.3(3) . . ?
C1 C2 Cl1 119.8(2) . . ?
C3 C2 Cl1 117.8(2) . . ?
C4 C3 C2 118.3(3) . . ?
C4 C3 H3 120.9 . . ?
C2 C3 H3 120.9 . . ?
C5 C4 C3 121.4(3) . . ?
C5 C4 Cl2 119.5(2) . . ?
C3 C4 Cl2 119.1(2) . . ?
C4 C5 C6 119.1(3) . . ?
C4 C5 H5 120.5 . . ?
C6 C5 H5 120.5 . . ?
C5 C6 C1 121.9(3) . . ?
C5 C6 H6 119.0 . . ?
C1 C6 H6 119.0 . . ?
O1 C7 C8 105.9(2) . . ?
O1 C7 C1 111.2(2) . . ?
C8 C7 C1 110.1(2) . . ?
O1 C7 H7 109.8 . . ?
C8 C7 H7 109.8 . . ?
C1 C7 H7 109.8 . . ?
N1 C8 C7 113.2(2) . . ?
N1 C8 H8A 108.9 . . ?
C7 C8 H8A 108.9 . . ?
N1 C8 H8B 108.9 . . ?
C7 C8 H8B 108.9 . . ?
H8A C8 H8B 107.8 . . ?
N2 C9 N1 111.7(3) . . ?
N2 C9 H9 124.1 . . ?
N1 C9 H9 124.1 . . ?
C11 C10 N2 110.1(2) . . ?
C11 C10 H10 124.9 . . ?
N2 C10 H10 124.9 . . ?
C10 C11 N1 106.4(2) . . ?
C10 C11 H11 126.8 . . ?
N1 C11 H11 126.8 . . ?
O1 C12 C14 108.4(2) . . ?
O1 C12 H12A 110.0 . . ?
C14 C12 H12A 110.0 . . ?
O1 C12 H12B 110.0 . . ?
C14 C12 H12B 110.0 . . ?
H12A C12 H12B 108.4 . . ?
C14 C13 Cl3 126.2(2) . . ?
C14 C13 S1 113.3(2) . . ?
Cl3 C13 S1 120.56(17) . . ?
C13 C14 C15 110.8(3) . . ?
C13 C14 C12 123.7(2) . . ?
C15 C14 C12 125.4(2) . . ?
C16 C15 C14 113.2(3) . . ?
C16 C15 H15 123.4 . . ?
C14 C15 H15 123.4 . . ?
C15 C16 S1 112.1(2) . . ?
C15 C16 H16 123.9 . . ?
S1 C16 H16 123.9 . . ?
C18 C17 C19 119.9(3) . 2_386 ?
C18 C17 C20 122.2(3) . . ?
C19 C17 C20 117.9(3) 2_386 . ?
C19 C18 C17 120.5(3) . . ?
C19 C18 H18 119.8 . . ?
C17 C18 H18 119.8 . . ?
C18 C19 C17 119.6(3) . 2_386 ?
C18 C19 H19 120.2 . . ?
C17 C19 H19 120.2 2_386 . ?
O2 C20 O3 123.9(3) . . ?
O2 C20 C17 123.3(3) . . ?
O3 C20 C17 112.8(3) . . ?
C9 N1 C11 106.6(2) . . ?
C9 N1 C8 125.8(2) . . ?
C11 N1 C8 127.5(2) . . ?
C9 N2 C10 105.2(2) . . ?
C12 O1 C7 113.50(19) . . ?
C20 O3 H3A 109.5 . . ?
C16 S1 C13 90.59(14) . . ?

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
C6 C1 C2 C3 -0.5(4) . . . . ?
C7 C1 C2 C3 179.4(3) . . . . ?
C6 C1 C2 Cl1 178.8(2) . . . . ?
C7 C1 C2 Cl1 -1.3(4) . . . . ?
C1 C2 C3 C4 -0.8(5) . . . . ?
Cl1 C2 C3 C4 180.0(2) . . . . ?
C2 C3 C4 C5 1.2(5) . . . . ?
C2 C3 C4 Cl2 -179.3(2) . . . . ?
C3 C4 C5 C6 -0.4(5) . . . . ?
Cl2 C4 C5 C6 -179.9(2) . . . . ?
C4 C5 C6 C1 -0.9(5) . . . . ?
C2 C1 C6 C5 1.3(4) . . . . ?
C7 C1 C6 C5 -178.6(3) . . . . ?
C2 C1 C7 O1 -153.1(2) . . . . ?
C6 C1 C7 O1 26.8(3) . . . . ?
C2 C1 C7 C8 89.8(3) . . . . ?
C6 C1 C7 C8 -90.4(3) . . . . ?
O1 C7 C8 N1 69.3(3) . . . . ?
C1 C7 C8 N1 -170.4(2) . . . . ?
N2 C10 C11 N1 0.5(3) . . . . ?
Cl3 C13 C14 C15 -178.2(2) . . . . ?
S1 C13 C14 C15 0.2(3) . . . . ?
Cl3 C13 C14 C12 0.1(4) . . . . ?
S1 C13 C14 C12 178.5(2) . . . . ?
O1 C12 C14 C13 175.6(3) . . . . ?
O1 C12 C14 C15 -6.3(4) . . . . ?
C13 C14 C15 C16 -0.4(4) . . . . ?
C12 C14 C15 C16 -178.7(3) . . . . ?
C14 C15 C16 S1 0.4(4) . . . . ?
C19 C17 C18 C19 -0.7(5) 2_386 . . . ?
C20 C17 C18 C19 179.4(3) . . . . ?
C17 C18 C19 C17 0.7(5) . . . 2_386 ?
C18 C17 C20 O2 175.8(3) . . . . ?
C19 C17 C20 O2 -4.1(5) 2_386 . . . ?
C18 C17 C20 O3 -4.6(4) . . . . ?
C19 C17 C20 O3 175.5(3) 2_386 . . . ?
N2 C9 N1 C11 0.3(3) . . . . ?
N2 C9 N1 C8 179.8(2) . . . . ?
C10 C11 N1 C9 -0.5(3) . . . . ?
C10 C11 N1 C8 -179.9(2) . . . . ?
C7 C8 N1 C9 122.9(3) . . . . ?
C7 C8 N1 C11 -57.7(4) . . . . ?
N1 C9 N2 C10 0.0(3) . . . . ?
C11 C10 N2 C9 -0.3(3) . . . . ?
C14 C12 O1 C7 173.0(2) . . . . ?
C8 C7 O1 C12 -164.8(2) . . . . ?
C1 C7 O1 C12 75.5(3) . . . . ?
C15 C16 S1 C13 -0.3(3) . . . . ?
C14 C13 S1 C16 0.0(3) . . . . ?
Cl3 C13 S1 C16 178.6(2) . . . . ?

_refine_diff_density_max         0.440
_refine_diff_density_min         -0.588
_refine_diff_density_rms         0.109

####################################################################### 
# 
# 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_TCZ-PTSA
_database_code_depnum_ccdc_archive 'CCDC 2285614'
loop_
_audit_author_name
_audit_author_address
'Tejender Thakur'
;CSIR Central Drug Research Institute
India
;
_audit_update_record             
;
2023-07-31 deposited with the CCDC.	2023-11-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            'Tioconazole-p-tolunesulfonate salt'
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H14 Cl3 N2 O S, C7 O3 S'
_chemical_formula_sum            'C23 H14 Cl3 N2 O4 S2'
_chemical_formula_weight         552.83

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'
Cl Cl 0.1484 0.1585 '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           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                   28.7499(12)
_cell_length_b                   6.6873(5)
_cell_length_c                   26.7737(10)
_cell_angle_alpha                90
_cell_angle_beta                 106.370(4)
_cell_angle_gamma                90
_cell_volume                     4938.8(5)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    8898
_cell_measurement_theta_min      2.4880
_cell_measurement_theta_max      31.2740

_exptl_crystal_description       platelet
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.487
_exptl_crystal_F_000             2248
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.573
_shelx_estimated_absorpt_T_min   0.904
_shelx_estimated_absorpt_T_max   0.956
_exptl_absorpt_correction_T_min  0.53198
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_source_power             0.0
_diffrn_source_voltage           50.0
_diffrn_source_current           0.6
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   MicroMax003_Mo
_diffrn_radiation_monochromator  Confocal
_diffrn_measurement_specimen_support Loop
_diffrn_detector                 CCD
_diffrn_measurement_device       
;
AFC12 (Right): Kappa 3 circle
;
_diffrn_measurement_device_type  
;
Rigaku Saturn724+ (4x4 bin mode)
;
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_details      
;
scan:
	Number of images: 200
	           Slice: -30.0000 - 70.0000
	     Image width: 0.5000
	        Exp time: 8.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 60.0000
	             Phi: 0.0000
	             XTD: 44.9385
	          2theta: -19.6987
scan:
	Number of images: 200
	           Slice: -30.0000 - 70.0000
	     Image width: 0.5000
	        Exp time: 8.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 60.0000
	             Phi: 90.0000
	             XTD: 44.9385
	          2theta: -19.6987
scan:
	Number of images: 200
	           Slice: -110.0000 - -10.0000
	     Image width: 0.5000
	        Exp time: 8.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: -60.0000
	             Phi: 180.0000
	             XTD: 44.9385
	          2theta: -19.6987
scan:
	Number of images: 200
	           Slice: -110.0000 - -10.0000
	     Image width: 0.5000
	        Exp time: 8.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: -60.0000
	             Phi: 180.0000
	             XTD: 44.9385
	          2theta: -19.6987

;
_diffrn_reflns_number            24527
_diffrn_reflns_av_unetI/netI     0.0895
_diffrn_reflns_av_R_equivalents  0.1301
_diffrn_reflns_limit_h_min       -42
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_theta_min         2.933
_diffrn_reflns_theta_max         31.292
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.881
_diffrn_measured_fraction_theta_full 0.976
_diffrn_reflns_Laue_measured_fraction_max 0.881
_diffrn_reflns_Laue_measured_fraction_full 0.976
_diffrn_reflns_point_group_measured_fraction_max 0.881
_diffrn_reflns_point_group_measured_fraction_full 0.976
_reflns_number_total             7127
_reflns_number_gt                4680
_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       'CrystalClear-SM Expert 2.1 b28 (Rigaku, 2013)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_structure_solution    'SHELXS-2013/1 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'
_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)+(0.0985P)²+9.0967P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   direct
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.0013(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         7127
_refine_ls_number_parameters     307
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1162
_refine_ls_R_factor_gt           0.0770
_refine_ls_wR_factor_ref         0.2195
_refine_ls_wR_factor_gt          0.1836
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.040
_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
C1 C 0.16778(10) 0.1928(6) 0.41395(12) 0.0291(8) Uani 1 1 d . . . . .
C2 C 0.19124(11) 0.0550(6) 0.45152(12) 0.0317(8) Uani 1 1 d . . . . .
C3 C 0.20125(12) 0.0898(7) 0.50449(12) 0.0353(9) Uani 1 1 d . . . . .
H3 H 0.217006 -0.007836 0.529287 0.042 Uiso 1 1 calc R U . . .
C4 C 0.18740(12) 0.2721(7) 0.51974(12) 0.0355(9) Uani 1 1 d . . . . .
C5 C 0.16482(12) 0.4179(7) 0.48442(13) 0.0360(9) Uani 1 1 d . . . . .
H5 H 0.156393 0.543578 0.495940 0.043 Uiso 1 1 calc R U . . .
C6 C 0.15480(12) 0.3748(7) 0.43138(13) 0.0361(9) Uani 1 1 d . . . . .
H6 H 0.138746 0.472048 0.406632 0.043 Uiso 1 1 calc R U . . .
C7 C 0.15160(11) 0.1438(6) 0.35598(11) 0.0287(7) Uani 1 1 d . . . . .
H7 H 0.173920 0.043148 0.347435 0.034 Uiso 1 1 calc R U . . .
C8 C 0.10038(12) 0.0585(6) 0.34437(11) 0.0325(8) Uani 1 1 d . . . . .
H8A H 0.101353 -0.067006 0.364253 0.039 Uiso 1 1 calc R U . . .
H8B H 0.079538 0.154687 0.356186 0.039 Uiso 1 1 calc R U . . .
C9 C 0.07493(11) -0.1595(7) 0.26638(13) 0.0339(8) Uani 1 1 d . . . . .
H9 H 0.085866 -0.282691 0.283305 0.041 Uiso 1 1 calc R U . . .
C10 C 0.04251(12) 0.0608(7) 0.20591(13) 0.0366(9) Uani 1 1 d . . . . .
H10 H 0.026760 0.117763 0.172978 0.044 Uiso 1 1 calc R U . . .
C11 C 0.05882(12) 0.1609(7) 0.25145(14) 0.0386(9) Uani 1 1 d . . . . .
H11 H 0.056839 0.300751 0.256786 0.046 Uiso 1 1 calc R U . . .
C12 C 0.19447(11) 0.3735(6) 0.31696(13) 0.0336(8) Uani 1 1 d . . . . .
H12A H 0.211032 0.254344 0.308185 0.040 Uiso 1 1 calc R U . . .
H12B H 0.215583 0.433856 0.349179 0.040 Uiso 1 1 calc R U . . .
C13 C 0.20835(11) 0.6984(6) 0.27337(12) 0.0327(8) Uani 1 1 d . . . . .
C14 C 0.18460(11) 0.5218(6) 0.27326(12) 0.0312(8) Uani 1 1 d . . . . .
C15 C 0.14895(12) 0.4927(7) 0.22419(12) 0.0341(8) Uani 1 1 d . . . . .
H15 H 0.128942 0.377302 0.216129 0.041 Uiso 1 1 calc R U . . .
C16 C 0.14661(12) 0.6455(7) 0.19053(13) 0.0387(9) Uani 1 1 d . . . . .
H16 H 0.124548 0.650289 0.156639 0.046 Uiso 1 1 calc R U . . .
C17 C 0.04008(12) 0.6397(7) 0.44159(13) 0.0372(9) Uani 1 1 d . . . . .
C18A C 0.0572(4) 0.5567(17) 0.4850(4) 0.025(2) Uiso 0.386(9) 1 d . . P . .
C19A C 0.0728(3) 0.6660(19) 0.5330(4) 0.026(2) Uiso 0.386(9) 1 d . . P . .
C20A C 0.0663(4) 0.8704(18) 0.5327(4) 0.033(2) Uiso 0.386(9) 1 d . . P . .
C21A C 0.0425(5) 0.968(2) 0.4873(5) 0.053(3) Uiso 0.386(9) 1 d . . P . .
C22A C 0.0274(4) 0.8605(18) 0.4384(4) 0.042(3) Uiso 0.386(9) 1 d . . P . .
C23A C 0.0839(4) 0.9790(19) 0.5852(4) 0.039(3) Uiso 0.386(9) 1 d . . P . .
C18B C 0.0486(3) 0.5058(12) 0.4882(3) 0.0339(16) Uiso 0.614(9) 1 d . . P . .
C19B C 0.0683(2) 0.5946(13) 0.5371(2) 0.0324(15) Uiso 0.614(9) 1 d . . P . .
C20B C 0.0804(2) 0.7992(13) 0.5409(2) 0.0345(14) Uiso 0.614(9) 1 d . . P . .
C21B C 0.0737(3) 0.9185(11) 0.4957(3) 0.0424(18) Uiso 0.614(9) 1 d . . P . .
C22B C 0.0533(2) 0.8309(10) 0.4467(2) 0.0330(14) Uiso 0.614(9) 1 d . . P . .
C23B C 0.1019(3) 0.8951(15) 0.5954(3) 0.054(2) Uiso 0.614(9) 1 d . . P . .
N1 N 0.07905(10) 0.0176(5) 0.28880(10) 0.0316(7) Uani 1 1 d . . . . .
N2 N 0.05278(10) -0.1358(6) 0.21589(11) 0.0355(8) Uani 1 1 d . . . . .
O1 O 0.14884(8) 0.3180(4) 0.32441(8) 0.0304(6) Uani 1 1 d . . . . .
O2 O 0.02243(9) 0.3075(4) 0.39016(9) 0.0373(6) Uani 1 1 d . . . . .
O3 O 0.04849(8) 0.5930(5) 0.34851(9) 0.0382(6) Uani 1 1 d . . . . .
O4 O -0.03224(8) 0.5841(5) 0.35908(10) 0.0413(7) Uani 1 1 d . . . . .
Cl1 Cl 0.20736(4) -0.17796(17) 0.43195(3) 0.0442(3) Uani 1 1 d . . . . .
Cl2 Cl 0.19842(3) 0.32053(18) 0.58627(3) 0.0434(3) Uani 1 1 d . . . . .
Cl3 Cl 0.25505(3) 0.79481(17) 0.32259(3) 0.0397(3) Uani 1 1 d . . . . .
S1 S 0.18797(3) 0.82968(18) 0.21594(3) 0.0397(3) Uani 1 1 d . . . . .
S2 S 0.01842(3) 0.51993(16) 0.38012(3) 0.0317(2) Uani 1 1 d . . . . .
H2N H 0.0470(16) -0.231(7) 0.1980(17) 0.043(13) 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
C1 C2 1.390(5) . ?
C1 C6 1.392(5) . ?
C1 C7 1.525(4) . ?
C2 C3 1.385(4) . ?
C2 Cl1 1.747(4) . ?
C3 C4 1.380(6) . ?
C3 H3 0.9500 . ?
C4 C5 1.386(5) . ?
C4 Cl2 1.749(3) . ?
C5 C6 1.397(5) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 O1 1.428(4) . ?
C7 C8 1.527(5) . ?
C7 H7 1.0000 . ?
C8 N1 1.466(4) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 N1 1.318(5) . ?
C9 N2 1.331(4) . ?
C9 H9 0.9500 . ?
C10 C11 1.354(5) . ?
C10 N2 1.357(6) . ?
C10 H10 0.9500 . ?
C11 N1 1.389(5) . ?
C11 H11 0.9500 . ?
C12 O1 1.430(4) . ?
C12 C14 1.499(5) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.364(5) . ?
C13 Cl3 1.720(3) . ?
C13 S1 1.723(4) . ?
C14 C15 1.434(5) . ?
C15 C16 1.352(5) . ?
C15 H15 0.9500 . ?
C16 S1 1.714(4) . ?
C16 H16 0.9500 . ?
C17 C18A 1.256(10) . ?
C17 C22B 1.330(7) . ?
C17 C18B 1.499(8) . ?
C17 C22A 1.518(13) . ?
C17 S2 1.778(4) . ?
C18A C19B 1.365(11) . ?
C18A C19A 1.436(13) . ?
C19A C19B 0.515(12) . ?
C19A C20B 0.927(12) . ?
C19A C20A 1.379(16) . ?
C19A C18B 1.612(13) . ?
C19A C21B 1.965(14) . ?
C20A C20B 0.623(11) . ?
C20A C21B 1.118(11) . ?
C20A C21A 1.380(16) . ?
C20A C23A 1.534(14) . ?
C20A C23B 1.709(13) . ?
C20A C19B 1.848(14) . ?
C21A C21B 0.922(13) . ?
C21A C22A 1.448(16) . ?
C21A C22B 1.518(14) . ?
C21A C20B 1.907(15) . ?
C22A C22B 0.741(11) . ?
C22A C21B 1.768(13) . ?
C23A C23B 0.760(12) . ?
C23A C20B 1.671(14) . ?
C18B C19B 1.403(9) . ?
C19B C20B 1.408(10) . ?
C20B C21B 1.417(10) . ?
C20B C23B 1.553(10) . ?
C21B C22B 1.405(9) . ?
N2 H2N 0.78(5) . ?
O2 S2 1.444(3) . ?
O3 S2 1.454(2) . ?
O4 S2 1.470(2) . ?

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
C2 C1 C6 117.3(3) . . ?
C2 C1 C7 122.7(3) . . ?
C6 C1 C7 119.7(3) . . ?
C3 C2 C1 123.2(4) . . ?
C3 C2 Cl1 117.4(3) . . ?
C1 C2 Cl1 119.3(3) . . ?
C4 C3 C2 117.2(3) . . ?
C4 C3 H3 121.4 . . ?
C2 C3 H3 121.4 . . ?
C3 C4 C5 122.6(3) . . ?
C3 C4 Cl2 118.7(3) . . ?
C5 C4 Cl2 118.7(3) . . ?
C4 C5 C6 118.1(4) . . ?
C4 C5 H5 120.9 . . ?
C6 C5 H5 120.9 . . ?
C1 C6 C5 121.5(4) . . ?
C1 C6 H6 119.2 . . ?
C5 C6 H6 119.2 . . ?
O1 C7 C1 112.2(3) . . ?
O1 C7 C8 107.1(3) . . ?
C1 C7 C8 106.7(2) . . ?
O1 C7 H7 110.2 . . ?
C1 C7 H7 110.2 . . ?
C8 C7 H7 110.2 . . ?
N1 C8 C7 112.3(2) . . ?
N1 C8 H8A 109.1 . . ?
C7 C8 H8A 109.1 . . ?
N1 C8 H8B 109.1 . . ?
C7 C8 H8B 109.1 . . ?
H8A C8 H8B 107.9 . . ?
N1 C9 N2 108.1(4) . . ?
N1 C9 H9 125.9 . . ?
N2 C9 H9 125.9 . . ?
C11 C10 N2 107.5(3) . . ?
C11 C10 H10 126.2 . . ?
N2 C10 H10 126.2 . . ?
C10 C11 N1 106.0(4) . . ?
C10 C11 H11 127.0 . . ?
N1 C11 H11 127.0 . . ?
O1 C12 C14 107.5(3) . . ?
O1 C12 H12A 110.2 . . ?
C14 C12 H12A 110.2 . . ?
O1 C12 H12B 110.2 . . ?
C14 C12 H12B 110.2 . . ?
H12A C12 H12B 108.5 . . ?
C14 C13 Cl3 127.5(3) . . ?
C14 C13 S1 113.3(2) . . ?
Cl3 C13 S1 119.2(2) . . ?
C13 C14 C15 110.4(3) . . ?
C13 C14 C12 125.9(3) . . ?
C15 C14 C12 123.7(4) . . ?
C16 C15 C14 113.4(4) . . ?
C16 C15 H15 123.3 . . ?
C14 C15 H15 123.3 . . ?
C15 C16 S1 112.3(3) . . ?
C15 C16 H16 123.8 . . ?
S1 C16 H16 123.8 . . ?
C18A C17 C22B 107.6(6) . . ?
C18A C17 C18B 15.6(5) . . ?
C22B C17 C18B 120.9(5) . . ?
C18A C17 C22A 120.5(7) . . ?
C22B C17 C22A 29.2(4) . . ?
C18B C17 C22A 127.5(5) . . ?
C18A C17 S2 126.9(6) . . ?
C22B C17 S2 123.0(4) . . ?
C18B C17 S2 115.7(4) . . ?
C22A C17 S2 111.7(5) . . ?
C17 C18A C19B 141.4(10) . . ?
C17 C18A C19A 123.0(10) . . ?
C19B C18A C19A 21.0(5) . . ?
C19B C19A C20B 154(2) . . ?
C19B C19A C20A 151.4(18) . . ?
C20B C19A C20A 21.9(7) . . ?
C19B C19A C18A 71.7(15) . . ?
C20B C19A C18A 133.5(11) . . ?
C20A C19A C18A 119.5(9) . . ?
C19B C19A C18B 57.4(14) . . ?
C20B C19A C18B 146.5(11) . . ?
C20A C19A C18B 128.7(8) . . ?
C18A C19A C18B 15.4(5) . . ?
C19B C19A C21B 161.1(17) . . ?
C20B C19A C21B 41.9(7) . . ?
C20A C19A C21B 33.6(5) . . ?
C18A C19A C21B 91.7(7) . . ?
C18B C19A C21B 105.0(6) . . ?
C20B C20A C21B 105.4(14) . . ?
C20B C20A C19A 33.6(11) . . ?
C21B C20A C19A 103.3(10) . . ?
C20B C20A C21A 141.5(16) . . ?
C21B C20A C21A 41.7(7) . . ?
C19A C20A C21A 120.3(10) . . ?
C20B C20A C23A 91.5(14) . . ?
C21B C20A C23A 125.4(10) . . ?
C19A C20A C23A 117.1(10) . . ?
C21A C20A C23A 122.5(11) . . ?
C20B C20A C23B 65.1(12) . . ?
C21B C20A C23B 129.2(9) . . ?
C19A C20A C23B 92.8(8) . . ?
C21A C20A C23B 146.2(10) . . ?
C23A C20A C23B 26.4(5) . . ?
C20B C20A C19B 37.8(12) . . ?
C21B C20A C19B 109.4(9) . . ?
C19A C20A C19B 7.7(5) . . ?
C21A C20A C19B 121.7(9) . . ?
C23A C20A C19B 114.7(8) . . ?
C23B C20A C19B 92.0(6) . . ?
C21B C21A C20A 53.8(9) . . ?
C21B C21A C22A 93.8(12) . . ?
C20A C21A C22A 120.8(12) . . ?
C21B C21A C22B 65.0(9) . . ?
C20A C21A C22B 101.3(10) . . ?
C22A C21A C22B 28.8(5) . . ?
C21B C21A C20B 45.2(8) . . ?
C20A C21A C20B 11.7(5) . . ?
C22A C21A C20B 110.5(10) . . ?
C22B C21A C20B 89.6(7) . . ?
C22B C22A C21A 80.9(12) . . ?
C22B C22A C17 61.2(10) . . ?
C21A C22A C17 115.2(9) . . ?
C22B C22A C21B 49.6(9) . . ?
C21A C22A C21B 31.4(6) . . ?
C17 C22A C21B 93.1(7) . . ?
C23B C23A C20A 89.7(13) . . ?
C23B C23A C20B 67.9(11) . . ?
C20A C23A C20B 21.9(4) . . ?
C19B C18B C17 116.9(7) . . ?
C19B C18B C19A 18.0(4) . . ?
C17 C18B C19A 99.0(6) . . ?
C19A C19B C18A 87.3(16) . . ?
C19A C19B C18B 104.6(16) . . ?
C18A C19B C18B 18.4(5) . . ?
C19A C19B C20B 16.8(13) . . ?
C18A C19B C20B 103.7(7) . . ?
C18B C19B C20B 120.4(6) . . ?
C19A C19B C20A 20.9(14) . . ?
C18A C19B C20A 97.3(7) . . ?
C18B C19B C20A 111.5(6) . . ?
C20B C19B C20A 15.7(4) . . ?
C20A C20B C19A 124.5(17) . . ?
C20A C20B C19B 126.5(15) . . ?
C19A C20B C19B 9.3(7) . . ?
C20A C20B C21B 49.5(11) . . ?
C19A C20B C21B 112.2(9) . . ?
C19B C20B C21B 120.9(6) . . ?
C20A C20B C23B 93.5(14) . . ?
C19A C20B C23B 128.2(9) . . ?
C19B C20B C23B 119.7(6) . . ?
C21B C20B C23B 119.4(7) . . ?
C20A C20B C23A 66.6(13) . . ?
C19A C20B C23A 144.8(9) . . ?
C19B C20B C23A 135.7(6) . . ?
C21B C20B C23A 99.6(7) . . ?
C23B C20B C23A 27.0(4) . . ?
C20A C20B C21A 26.8(11) . . ?
C19A C20B C21A 110.3(9) . . ?
C19B C20B C21A 116.3(6) . . ?
C21B C20B C21A 27.5(5) . . ?
C23B C20B C21A 117.0(7) . . ?
C23A C20B C21A 90.9(7) . . ?
C21A C21B C20A 84.5(11) . . ?
C21A C21B C22B 78.5(10) . . ?
C20A C21B C22B 125.1(9) . . ?
C21A C21B C20B 107.4(10) . . ?
C20A C21B C20B 25.1(6) . . ?
C22B C21B C20B 118.9(7) . . ?
C21A C21B C22A 54.8(10) . . ?
C20A C21B C22A 115.0(8) . . ?
C22B C21B C22A 23.7(4) . . ?
C20B C21B C22A 120.4(6) . . ?
C21A C21B C19A 106.3(10) . . ?
C20A C21B C19A 43.1(7) . . ?
C22B C21B C19A 93.1(5) . . ?
C20B C21B C19A 25.9(4) . . ?
C22A C21B C19A 97.9(6) . . ?
C22A C22B C17 89.5(11) . . ?
C22A C22B C21B 106.8(12) . . ?
C17 C22B C21B 122.0(6) . . ?
C22A C22B C21A 70.3(11) . . ?
C17 C22B C21A 122.9(7) . . ?
C21B C22B C21A 36.5(5) . . ?
C23A C23B C20B 85.2(12) . . ?
C23A C23B C20A 63.8(11) . . ?
C20B C23B C20A 21.4(4) . . ?
C9 N1 C11 109.1(3) . . ?
C9 N1 C8 126.0(3) . . ?
C11 N1 C8 124.9(3) . . ?
C9 N2 C10 109.3(3) . . ?
C9 N2 H2N 119(4) . . ?
C10 N2 H2N 132(4) . . ?
C7 O1 C12 113.2(2) . . ?
C16 S1 C13 90.66(19) . . ?
O2 S2 O3 114.17(17) . . ?
O2 S2 O4 112.15(17) . . ?
O3 S2 O4 111.49(16) . . ?
O2 S2 C17 106.37(18) . . ?
O3 S2 C17 106.07(16) . . ?
O4 S2 C17 105.91(17) . . ?

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
C6 C1 C2 C3 1.1(5) . . . . ?
C7 C1 C2 C3 -172.5(3) . . . . ?
C6 C1 C2 Cl1 178.8(2) . . . . ?
C7 C1 C2 Cl1 5.1(4) . . . . ?
C1 C2 C3 C4 -0.8(5) . . . . ?
Cl1 C2 C3 C4 -178.5(3) . . . . ?
C2 C3 C4 C5 -0.7(5) . . . . ?
C2 C3 C4 Cl2 178.9(3) . . . . ?
C3 C4 C5 C6 1.6(5) . . . . ?
Cl2 C4 C5 C6 -177.9(3) . . . . ?
C2 C1 C6 C5 -0.1(5) . . . . ?
C7 C1 C6 C5 173.8(3) . . . . ?
C4 C5 C6 C1 -1.3(5) . . . . ?
C2 C1 C7 O1 -153.8(3) . . . . ?
C6 C1 C7 O1 32.7(4) . . . . ?
C2 C1 C7 C8 89.1(4) . . . . ?
C6 C1 C7 C8 -84.4(4) . . . . ?
O1 C7 C8 N1 55.7(4) . . . . ?
C1 C7 C8 N1 176.0(3) . . . . ?
N2 C10 C11 N1 -0.1(4) . . . . ?
Cl3 C13 C14 C15 -178.1(3) . . . . ?
S1 C13 C14 C15 0.7(4) . . . . ?
Cl3 C13 C14 C12 0.3(5) . . . . ?
S1 C13 C14 C12 179.1(3) . . . . ?
O1 C12 C14 C13 132.9(3) . . . . ?
O1 C12 C14 C15 -48.9(4) . . . . ?
C13 C14 C15 C16 -1.1(4) . . . . ?
C12 C14 C15 C16 -179.5(3) . . . . ?
C14 C15 C16 S1 1.1(4) . . . . ?
C22B C17 C18A C19B 33.1(15) . . . . ?
C18B C17 C18A C19B -117(3) . . . . ?
C22A C17 C18A C19B 4.2(17) . . . . ?
S2 C17 C18A C19B -164.5(11) . . . . ?
C22B C17 C18A C19A 19.2(11) . . . . ?
C18B C17 C18A C19A -131(3) . . . . ?
C22A C17 C18A C19A -9.7(13) . . . . ?
S2 C17 C18A C19A -178.4(6) . . . . ?
C17 C18A C19A C19B 155.2(16) . . . . ?
C17 C18A C19A C20B -17.0(19) . . . . ?
C19B C18A C19A C20B -172(3) . . . . ?
C17 C18A C19A C20A 4.0(14) . . . . ?
C19B C18A C19A C20A -151(2) . . . . ?
C17 C18A C19A C18B 135(3) . . . . ?
C19B C18A C19A C18B -21(2) . . . . ?
C17 C18A C19A C21B -15.7(10) . . . . ?
C19B C18A C19A C21B -170.9(17) . . . . ?
C19B C19A C20A C20B 118(4) . . . . ?
C18A C19A C20A C20B -136(2) . . . . ?
C18B C19A C20A C20B -151(2) . . . . ?
C21B C19A C20A C20B -97.9(19) . . . . ?
C19B C19A C20A C21B -144(4) . . . . ?
C20B C19A C20A C21B 97.9(19) . . . . ?
C18A C19A C20A C21B -37.6(13) . . . . ?
C18B C19A C20A C21B -52.6(13) . . . . ?
C19B C19A C20A C21A -103(4) . . . . ?
C20B C19A C20A C21A 139(2) . . . . ?
C18A C19A C20A C21A 3.8(15) . . . . ?
C18B C19A C20A C21A -11.2(16) . . . . ?
C21B C19A C20A C21A 41.4(8) . . . . ?
C19B C19A C20A C23A 74(4) . . . . ?
C20B C19A C20A C23A -44.2(17) . . . . ?
C18A C19A C20A C23A -179.8(8) . . . . ?
C18B C19A C20A C23A 165.2(8) . . . . ?
C21B C19A C20A C23A -142.2(14) . . . . ?
C19B C19A C20A C23B 84(4) . . . . ?
C20B C19A C20A C23B -33.5(16) . . . . ?
C18A C19A C20A C23B -169.0(8) . . . . ?
C18B C19A C20A C23B 176.0(8) . . . . ?
C21B C19A C20A C23B -131.4(11) . . . . ?
C20B C19A C20A C19B -118(4) . . . . ?
C18A C19A C20A C19B 107(4) . . . . ?
C18B C19A C20A C19B 92(4) . . . . ?
C21B C19A C20A C19B 144(4) . . . . ?
C20B C20A C21A C21B -40(3) . . . . ?
C19A C20A C21A C21B -75.2(13) . . . . ?
C23A C20A C21A C21B 108.5(13) . . . . ?
C23B C20A C21A C21B 91.7(18) . . . . ?
C19B C20A C21A C21B -84.0(12) . . . . ?
C20B C20A C21A C22A 30(3) . . . . ?
C21B C20A C21A C22A 70.1(13) . . . . ?
C19A C20A C21A C22A -5.1(17) . . . . ?
C23A C20A C21A C22A 178.7(10) . . . . ?
C23B C20A C21A C22A 161.8(13) . . . . ?
C19B C20A C21A C22A -13.8(16) . . . . ?
C20B C20A C21A C22B 7(3) . . . . ?
C21B C20A C21A C22B 47.2(9) . . . . ?
C19A C20A C21A C22B -28.0(13) . . . . ?
C23A C20A C21A C22B 155.7(9) . . . . ?
C23B C20A C21A C22B 138.9(14) . . . . ?
C19B C20A C21A C22B -36.8(12) . . . . ?
C21B C20A C21A C20B 40(3) . . . . ?
C19A C20A C21A C20B -35(2) . . . . ?
C23A C20A C21A C20B 148(3) . . . . ?
C23B C20A C21A C20B 131(4) . . . . ?
C19B C20A C21A C20B -44(2) . . . . ?
C21B C21A C22A C22B -3.0(14) . . . . ?
C20A C21A C22A C22B -52.4(15) . . . . ?
C20B C21A C22A C22B -46.1(12) . . . . ?
C21B C21A C22A C17 49.1(13) . . . . ?
C20A C21A C22A C17 -0.4(15) . . . . ?
C22B C21A C22A C17 52.1(10) . . . . ?
C20B C21A C22A C17 6.0(12) . . . . ?
C20A C21A C22A C21B -49.5(10) . . . . ?
C22B C21A C22A C21B 3.0(14) . . . . ?
C20B C21A C22A C21B -43.2(8) . . . . ?
C18A C17 C22A C22B 70.6(12) . . . . ?
C18B C17 C22A C22B 87.4(11) . . . . ?
S2 C17 C22A C22B -119.2(9) . . . . ?
C18A C17 C22A C21A 7.8(12) . . . . ?
C22B C17 C22A C21A -62.7(11) . . . . ?
C18B C17 C22A C21A 24.7(12) . . . . ?
S2 C17 C22A C21A 178.1(7) . . . . ?
C18A C17 C22A C21B 31.0(9) . . . . ?
C22B C17 C22A C21B -39.5(8) . . . . ?
C18B C17 C22A C21B 47.9(8) . . . . ?
S2 C17 C22A C21B -158.7(4) . . . . ?
C20B C20A C23A C23B 2.1(16) . . . . ?
C21B C20A C23A C23B -108.1(16) . . . . ?
C19A C20A C23A C23B 24.8(15) . . . . ?
C21A C20A C23A C23B -158.8(13) . . . . ?
C19B C20A C23A C23B 32.9(14) . . . . ?
C21B C20A C23A C20B -110.1(19) . . . . ?
C19A C20A C23A C20B 22.7(10) . . . . ?
C21A C20A C23A C20B -161(2) . . . . ?
C23B C20A C23A C20B -2.1(17) . . . . ?
C19B C20A C23A C20B 30.8(10) . . . . ?
C18A C17 C18B C19B 37(2) . . . . ?
C22B C17 C18B C19B 3.6(8) . . . . ?
C22A C17 C18B C19B -31.0(10) . . . . ?
S2 C17 C18B C19B 176.4(5) . . . . ?
C18A C17 C18B C19A 35(2) . . . . ?
C22B C17 C18B C19A 1.2(7) . . . . ?
C22A C17 C18B C19A -33.5(9) . . . . ?
S2 C17 C18B C19A 174.0(4) . . . . ?
C20B C19A C18B C19B -165(3) . . . . ?
C20A C19A C18B C19B -145(2) . . . . ?
C18A C19A C18B C19B 157(3) . . . . ?
C21B C19A C18B C19B -172.5(19) . . . . ?
C19B C19A C18B C17 172.9(16) . . . . ?
C20B C19A C18B C17 8.1(19) . . . . ?
C20A C19A C18B C17 27.5(11) . . . . ?
C18A C19A C18B C17 -30.4(19) . . . . ?
C21B C19A C18B C17 0.4(6) . . . . ?
C20B C19A C19B C18A 167(4) . . . . ?
C20A C19A C19B C18A 119(4) . . . . ?
C18B C19A C19B C18A 6.3(7) . . . . ?
C21B C19A C19B C18A 29(5) . . . . ?
C20B C19A C19B C18B 161(4) . . . . ?
C20A C19A C19B C18B 112(3) . . . . ?
C18A C19A C19B C18B -6.3(7) . . . . ?
C21B C19A C19B C18B 23(6) . . . . ?
C20A C19A C19B C20B -48(4) . . . . ?
C18A C19A C19B C20B -167(4) . . . . ?
C18B C19A C19B C20B -161(4) . . . . ?
C21B C19A C19B C20B -138(9) . . . . ?
C20B C19A C19B C20A 48(4) . . . . ?
C18A C19A C19B C20A -119(4) . . . . ?
C18B C19A C19B C20A -112(3) . . . . ?
C21B C19A C19B C20A -89(6) . . . . ?
C17 C18A C19B C19A -34(2) . . . . ?
C17 C18A C19B C18B 126(3) . . . . ?
C19A C18A C19B C18B 160(2) . . . . ?
C17 C18A C19B C20B -30.5(16) . . . . ?
C19A C18A C19B C20B 3.8(13) . . . . ?
C17 C18A C19B C20A -15.9(15) . . . . ?
C19A C18A C19B C20A 18.4(13) . . . . ?
C17 C18B C19B C19A -7.9(18) . . . . ?
C17 C18B C19B C18A -28.4(17) . . . . ?
C19A C18B C19B C18A -20(2) . . . . ?
C17 C18B C19B C20B -1.6(9) . . . . ?
C19A C18B C19B C20B 6.4(13) . . . . ?
C17 C18B C19B C20A 12.9(8) . . . . ?
C19A C18B C19B C20A 20.8(14) . . . . ?
C20B C20A C19B C19A -53(4) . . . . ?
C21B C20A C19B C19A 37(4) . . . . ?
C21A C20A C19B C19A 82(4) . . . . ?
C23A C20A C19B C19A -110(4) . . . . ?
C23B C20A C19B C19A -96(4) . . . . ?
C20B C20A C19B C18A -115.3(17) . . . . ?
C21B C20A C19B C18A -25.0(10) . . . . ?
C19A C20A C19B C18A -62(4) . . . . ?
C21A C20A C19B C18A 19.5(11) . . . . ?
C23A C20A C19B C18A -172.1(8) . . . . ?
C23B C20A C19B C18A -158.1(7) . . . . ?
C20B C20A C19B C18B -127.4(16) . . . . ?
C21B C20A C19B C18B -37.2(10) . . . . ?
C19A C20A C19B C18B -74(4) . . . . ?
C21A C20A C19B C18B 7.4(12) . . . . ?
C23A C20A C19B C18B 175.8(7) . . . . ?
C23B C20A C19B C18B -170.2(6) . . . . ?
C21B C20A C19B C20B 90.2(17) . . . . ?
C19A C20A C19B C20B 53(4) . . . . ?
C21A C20A C19B C20B 135(2) . . . . ?
C23A C20A C19B C20B -56.8(15) . . . . ?
C23B C20A C19B C20B -42.8(15) . . . . ?
C21B C20A C20B C19A -90.9(17) . . . . ?
C21A C20A C20B C19A -65(3) . . . . ?
C23A C20A C20B C19A 141.6(13) . . . . ?
C23B C20A C20B C19A 142.6(16) . . . . ?
C19B C20A C20B C19A 11.1(9) . . . . ?
C21B C20A C20B C19B -102.0(14) . . . . ?
C19A C20A C20B C19B -11.1(9) . . . . ?
C21A C20A C20B C19B -76(3) . . . . ?
C23A C20A C20B C19B 130.5(11) . . . . ?
C23B C20A C20B C19B 131.5(13) . . . . ?
C19A C20A C20B C21B 90.9(17) . . . . ?
C21A C20A C20B C21B 26.2(18) . . . . ?
C23A C20A C20B C21B -127.5(13) . . . . ?
C23B C20A C20B C21B -126.5(10) . . . . ?
C19B C20A C20B C21B 102.0(14) . . . . ?
C21B C20A C20B C23B 126.5(10) . . . . ?
C19A C20A C20B C23B -142.6(16) . . . . ?
C21A C20A C20B C23B 153(2) . . . . ?
C23A C20A C20B C23B -1.0(8) . . . . ?
C19B C20A C20B C23B -131.5(13) . . . . ?
C21B C20A C20B C23A 127.5(13) . . . . ?
C19A C20A C20B C23A -141.6(13) . . . . ?
C21A C20A C20B C23A 154(3) . . . . ?
C23B C20A C20B C23A 1.0(8) . . . . ?
C19B C20A C20B C23A -130.5(11) . . . . ?
C21B C20A C20B C21A -26.2(18) . . . . ?
C19A C20A C20B C21A 65(3) . . . . ?
C23A C20A C20B C21A -154(3) . . . . ?
C23B C20A C20B C21A -153(2) . . . . ?
C19B C20A C20B C21A 76(3) . . . . ?
C19B C19A C20B C20A -106(5) . . . . ?
C18A C19A C20B C20A 57(2) . . . . ?
C18B C19A C20B C20A 44(3) . . . . ?
C21B C19A C20B C20A 55.2(16) . . . . ?
C20A C19A C20B C19B 106(5) . . . . ?
C18A C19A C20B C19B 163(6) . . . . ?
C18B C19A C20B C19B 150(6) . . . . ?
C21B C19A C20B C19B 161(4) . . . . ?
C19B C19A C20B C21B -161(4) . . . . ?
C20A C19A C20B C21B -55.2(16) . . . . ?
C18A C19A C20B C21B 2.0(17) . . . . ?
C18B C19A C20B C21B -11(2) . . . . ?
C19B C19A C20B C23B 24(5) . . . . ?
C20A C19A C20B C23B 130(2) . . . . ?
C18A C19A C20B C23B -173.3(9) . . . . ?
C18B C19A C20B C23B 173.6(11) . . . . ?
C21B C19A C20B C23B -175.2(14) . . . . ?
C19B C19A C20B C23A -8(6) . . . . ?
C20A C19A C20B C23A 98(2) . . . . ?
C18A C19A C20B C23A 155.2(12) . . . . ?
C18B C19A C20B C23A 142.0(14) . . . . ?
C21B C19A C20B C23A 153(2) . . . . ?
C19B C19A C20B C21A -132(4) . . . . ?
C20A C19A C20B C21A -25.8(15) . . . . ?
C18A C19A C20B C21A 31.5(16) . . . . ?
C18B C19A C20B C21A 18(2) . . . . ?
C21B C19A C20B C21A 29.5(5) . . . . ?
C19A C19B C20B C20A 81(5) . . . . ?
C18A C19B C20B C20A 67.4(17) . . . . ?
C18B C19B C20B C20A 59.0(18) . . . . ?
C18A C19B C20B C19A -13(4) . . . . ?
C18B C19B C20B C19A -22(4) . . . . ?
C20A C19B C20B C19A -81(5) . . . . ?
C19A C19B C20B C21B 21(5) . . . . ?
C18A C19B C20B C21B 7.3(9) . . . . ?
C18B C19B C20B C21B -1.1(10) . . . . ?
C20A C19B C20B C21B -60.1(15) . . . . ?
C19A C19B C20B C23B -159(5) . . . . ?
C18A C19B C20B C23B -171.9(7) . . . . ?
C18B C19B C20B C23B 179.7(6) . . . . ?
C20A C19B C20B C23B 120.7(18) . . . . ?
C19A C19B C20B C23A 174(5) . . . . ?
C18A C19B C20B C23A 160.3(9) . . . . ?
C18B C19B C20B C23A 151.9(9) . . . . ?
C20A C19B C20B C23A 92.9(18) . . . . ?
C19A C19B C20B C21A 52(5) . . . . ?
C18A C19B C20B C21A 38.3(8) . . . . ?
C18B C19B C20B C21A 29.8(9) . . . . ?
C20A C19B C20B C21A -29.2(14) . . . . ?
C23B C23A C20B C20A -177.8(18) . . . . ?
C23B C23A C20B C19A 65(2) . . . . ?
C20A C23A C20B C19A -117(2) . . . . ?
C23B C23A C20B C19B 63.2(14) . . . . ?
C20A C23A C20B C19B -119.0(16) . . . . ?
C23B C23A C20B C21B -140.0(11) . . . . ?
C20A C23A C20B C21B 37.7(12) . . . . ?
C20A C23A C20B C23B 177.8(18) . . . . ?
C23B C23A C20B C21A -166.2(12) . . . . ?
C20A C23A C20B C21A 11.5(12) . . . . ?
C22A C21A C21B C20A -125.9(10) . . . . ?
C22B C21A C21B C20A -127.5(9) . . . . ?
C20B C21A C21B C20A -10.6(8) . . . . ?
C20A C21A C21B C22B 127.5(8) . . . . ?
C22A C21A C21B C22B 1.6(7) . . . . ?
C20B C21A C21B C22B 116.9(8) . . . . ?
C20A C21A C21B C20B 10.6(8) . . . . ?
C22A C21A C21B C20B -115.3(9) . . . . ?
C22B C21A C21B C20B -116.9(8) . . . . ?
C20A C21A C21B C22A 125.9(10) . . . . ?
C22B C21A C21B C22A -1.6(7) . . . . ?
C20B C21A C21B C22A 115.3(9) . . . . ?
C20A C21A C21B C19A 37.6(7) . . . . ?
C22A C21A C21B C19A -88.3(9) . . . . ?
C22B C21A C21B C19A -89.8(6) . . . . ?
C20B C21A C21B C19A 27.1(4) . . . . ?
C20B C20A C21B C21A 155.6(18) . . . . ?
C19A C20A C21B C21A 120.9(12) . . . . ?
C23A C20A C21B C21A -101.1(15) . . . . ?
C23B C20A C21B C21A -134.2(15) . . . . ?
C19B C20A C21B C21A 116.2(11) . . . . ?
C20B C20A C21B C22B 83.8(18) . . . . ?
C19A C20A C21B C22B 49.2(13) . . . . ?
C21A C20A C21B C22B -71.8(12) . . . . ?
C23A C20A C21B C22B -172.9(9) . . . . ?
C23B C20A C21B C22B 154.0(9) . . . . ?
C19B C20A C21B C22B 44.4(12) . . . . ?
C19A C20A C21B C20B -34.7(12) . . . . ?
C21A C20A C21B C20B -155.6(18) . . . . ?
C23A C20A C21B C20B 103(2) . . . . ?
C23B C20A C21B C20B 70.2(16) . . . . ?
C19B C20A C21B C20B -39.4(13) . . . . ?
C20B C20A C21B C22A 108.7(16) . . . . ?
C19A C20A C21B C22A 74.0(11) . . . . ?
C21A C20A C21B C22A -46.9(11) . . . . ?
C23A C20A C21B C22A -148.1(10) . . . . ?
C23B C20A C21B C22A 178.9(9) . . . . ?
C19B C20A C21B C22A 69.3(10) . . . . ?
C20B C20A C21B C19A 34.7(12) . . . . ?
C21A C20A C21B C19A -120.9(12) . . . . ?
C23A C20A C21B C19A 137.9(17) . . . . ?
C23B C20A C21B C19A 104.9(15) . . . . ?
C19B C20A C21B C19A -4.7(5) . . . . ?
C20A C20B C21B C21A -25.5(19) . . . . ?
C19A C20B C21B C21A 91.6(14) . . . . ?
C19B C20B C21B C21A 88.1(12) . . . . ?
C23B C20B C21B C21A -92.7(12) . . . . ?
C23A C20B C21B C21A -73.1(12) . . . . ?
C19A C20B C21B C20A 117.1(19) . . . . ?
C19B C20B C21B C20A 113.6(18) . . . . ?
C23B C20B C21B C20A -67.2(17) . . . . ?
C23A C20B C21B C20A -47.6(16) . . . . ?
C21A C20B C21B C20A 25.5(19) . . . . ?
C20A C20B C21B C22B -111.7(17) . . . . ?
C19A C20B C21B C22B 5.5(12) . . . . ?
C19B C20B C21B C22B 2.0(10) . . . . ?
C23B C20B C21B C22B -178.8(6) . . . . ?
C23A C20B C21B C22B -159.3(7) . . . . ?
C21A C20B C21B C22B -86.2(12) . . . . ?
C20A C20B C21B C22A -84.4(17) . . . . ?
C19A C20B C21B C22A 32.7(12) . . . . ?
C19B C20B C21B C22A 29.2(10) . . . . ?
C23B C20B C21B C22A -151.6(7) . . . . ?
C23A C20B C21B C22A -132.0(7) . . . . ?
C21A C20B C21B C22A -58.9(11) . . . . ?
C20A C20B C21B C19A -117.1(19) . . . . ?
C19B C20B C21B C19A -3.5(8) . . . . ?
C23B C20B C21B C19A 175.7(13) . . . . ?
C23A C20B C21B C19A -164.7(11) . . . . ?
C21A C20B C21B C19A -91.6(14) . . . . ?
C22B C22A C21B C21A 176.2(18) . . . . ?
C17 C22A C21B C21A -136.7(13) . . . . ?
C22B C22A C21B C20A -121.0(14) . . . . ?
C21A C22A C21B C20A 62.8(14) . . . . ?
C17 C22A C21B C20A -73.9(11) . . . . ?
C21A C22A C21B C22B -176.2(18) . . . . ?
C17 C22A C21B C22B 47.1(10) . . . . ?
C22B C22A C21B C20B -93.3(13) . . . . ?
C21A C22A C21B C20B 90.6(13) . . . . ?
C17 C22A C21B C20B -46.2(9) . . . . ?
C22B C22A C21B C19A -79.5(12) . . . . ?
C21A C22A C21B C19A 104.4(12) . . . . ?
C17 C22A C21B C19A -32.4(6) . . . . ?
C21A C22A C22B C17 125.4(7) . . . . ?
C21B C22A C22B C17 123.4(7) . . . . ?
C21A C22A C22B C21B 2.0(9) . . . . ?
C17 C22A C22B C21B -123.4(7) . . . . ?
C17 C22A C22B C21A -125.4(7) . . . . ?
C21B C22A C22B C21A -2.0(9) . . . . ?
C18A C17 C22B C22A -121.5(11) . . . . ?
C18B C17 C22B C22A -112.5(11) . . . . ?
S2 C17 C22B C22A 75.2(11) . . . . ?
C18A C17 C22B C21B -11.9(8) . . . . ?
C18B C17 C22B C21B -2.9(9) . . . . ?
C22A C17 C22B C21B 109.6(12) . . . . ?
S2 C17 C22B C21B -175.2(5) . . . . ?
C18A C17 C22B C21A -55.5(9) . . . . ?
C18B C17 C22B C21A -46.5(10) . . . . ?
C22A C17 C22B C21A 66.0(11) . . . . ?
S2 C17 C22B C21A 141.2(7) . . . . ?
C21A C21B C22B C22A -3.2(15) . . . . ?
C20A C21B C22B C22A 71.6(16) . . . . ?
C20B C21B C22B C22A 100.4(13) . . . . ?
C19A C21B C22B C22A 102.8(12) . . . . ?
C21A C21B C22B C17 -103.5(11) . . . . ?
C20A C21B C22B C17 -28.7(13) . . . . ?
C20B C21B C22B C17 0.1(10) . . . . ?
C22A C21B C22B C17 -100.3(13) . . . . ?
C19A C21B C22B C17 2.5(7) . . . . ?
C20A C21B C22B C21A 74.8(13) . . . . ?
C20B C21B C22B C21A 103.6(12) . . . . ?
C22A C21B C22B C21A 3.2(15) . . . . ?
C19A C21B C22B C21A 106.0(10) . . . . ?
C21B C21A C22B C22A 176.7(15) . . . . ?
C20A C21A C22B C22A 136.0(14) . . . . ?
C20B C21A C22B C22A 137.5(12) . . . . ?
C21B C21A C22B C17 100.7(10) . . . . ?
C20A C21A C22B C17 60.0(11) . . . . ?
C22A C21A C22B C17 -76.0(12) . . . . ?
C20B C21A C22B C17 61.5(8) . . . . ?
C20A C21A C22B C21B -40.7(8) . . . . ?
C22A C21A C22B C21B -176.7(15) . . . . ?
C20B C21A C22B C21B -39.2(7) . . . . ?
C20A C23A C23B C20B -0.8(7) . . . . ?
C20B C23A C23B C20A 0.8(7) . . . . ?
C20A C20B C23B C23A 2.1(16) . . . . ?
C19A C20B C23B C23A -138.4(15) . . . . ?
C19B C20B C23B C23A -134.1(12) . . . . ?
C21B C20B C23B C23A 46.7(13) . . . . ?
C21A C20B C23B C23A 15.5(13) . . . . ?
C19A C20B C23B C20A -140.4(19) . . . . ?
C19B C20B C23B C20A -136.2(15) . . . . ?
C21B C20B C23B C20A 44.6(12) . . . . ?
C23A C20B C23B C20A -2.1(16) . . . . ?
C21A C20B C23B C20A 13.4(11) . . . . ?
C20B C20A C23B C23A -177.7(18) . . . . ?
C21B C20A C23B C23A 92.3(17) . . . . ?
C19A C20A C23B C23A -158.0(13) . . . . ?
C21A C20A C23B C23A 33(2) . . . . ?
C19B C20A C23B C23A -150.4(12) . . . . ?
C21B C20A C23B C20B -90.0(17) . . . . ?
C19A C20A C23B C20B 19.7(10) . . . . ?
C21A C20A C23B C20B -149(2) . . . . ?
C23A C20A C23B C20B 177.7(18) . . . . ?
C19B C20A C23B C20B 27.3(10) . . . . ?
N2 C9 N1 C11 0.0(4) . . . . ?
N2 C9 N1 C8 178.6(3) . . . . ?
C10 C11 N1 C9 0.0(4) . . . . ?
C10 C11 N1 C8 -178.6(3) . . . . ?
C7 C8 N1 C9 102.6(4) . . . . ?
C7 C8 N1 C11 -79.0(4) . . . . ?
N1 C9 N2 C10 -0.1(4) . . . . ?
C11 C10 N2 C9 0.1(4) . . . . ?
C1 C7 O1 C12 83.9(3) . . . . ?
C8 C7 O1 C12 -159.4(3) . . . . ?
C14 C12 O1 C7 165.8(3) . . . . ?
C15 C16 S1 C13 -0.6(3) . . . . ?
C14 C13 S1 C16 -0.1(3) . . . . ?
Cl3 C13 S1 C16 178.8(2) . . . . ?
C18A C17 S2 O2 2.5(7) . . . . ?
C22B C17 S2 O2 162.4(4) . . . . ?
C18B C17 S2 O2 -10.2(4) . . . . ?
C22A C17 S2 O2 -167.0(5) . . . . ?
C18A C17 S2 O3 -119.4(6) . . . . ?
C22B C17 S2 O3 40.5(5) . . . . ?
C18B C17 S2 O3 -132.2(4) . . . . ?
C22A C17 S2 O3 71.0(5) . . . . ?
C18A C17 S2 O4 122.0(6) . . . . ?
C22B C17 S2 O4 -78.1(5) . . . . ?
C18B C17 S2 O4 109.2(4) . . . . ?
C22A C17 S2 O4 -47.5(5) . . . . ?

_refine_diff_density_max         0.674
_refine_diff_density_min         -0.665
_refine_diff_density_rms         0.108

####################################################################### 
# 
# 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_TCZ-SULH
_database_code_depnum_ccdc_archive 'CCDC 2296505'
loop_
_audit_author_name
_audit_author_address
'Tejender Thakur'
;CSIR Central Drug Research Institute
India
;
_audit_update_record             
;
2023-09-21 deposited with the CCDC.	2023-11-14 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT430_TCZ-SULH            
;
PROBLEM: Short Inter D...A Contact  O8       ..O9A      .       1.88 Ang.
RESPONSE: The observed short distances may be attributed to the positional disorder shown by O9 atom and was refined with positions O9A and O9B. 
;
_vrf_PLAT306_TCZ-SULH            
;
PROBLEM: Isolated Oxygen Atom (H-atoms Missing ?) .......         O8 Check
RESPONSE: Hydrogen atom positions for Atom O8 colun't not be located from difference density map.
;
_vrf_PLAT430_TCZ-SULH_2          
;
PROBLEM: Short Inter D...A Contact  O3       ..O9B      .       2.79 Ang.
RESPONSE: The observed short distances may be attributed to the positional disorder shown by O9 atom and was refined with positions O9A and O9B. 
;
# Added during the CSD deposition process: Thursday 21 September 2023 12:59 PM
# end Validation Reply Form

_audit_creation_method           SHELXL-2019/2
_shelx_SHELXL_version_number     2019/2
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         
'C16 H12 Cl3 N2 O S, C16 H14 Cl3 N2 O S, O4 S, 3(H2 O), 2(O)'
_chemical_formula_sum            'C32 H32 Cl6 N4 O11 S3'
_chemical_formula_weight         957.49

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'
Cl Cl 0.3639 0.7018 '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                   8.4631(3)
_cell_length_b                   12.0147(6)
_cell_length_c                   21.5955(18)
_cell_angle_alpha                82.360(9)
_cell_angle_beta                 88.440(6)
_cell_angle_gamma                88.592(3)
_cell_volume                     2175.1(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    297(2)
_cell_measurement_reflns_used    15978
_cell_measurement_theta_min      2.0630
_cell_measurement_theta_max      78.8530

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.462
_exptl_crystal_F_000             980
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.270
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    5.451
_shelx_estimated_absorpt_T_min   0.321
_shelx_estimated_absorpt_T_max   0.899
_exptl_absorpt_correction_T_min  0.36691
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.88a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.344
_oxdiff_exptl_absorpt_empirical_full_max 4.021
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      297(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_ambient_environment      air
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_type            HyPix
_diffrn_detector_area_resol_mean 10.0000
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0706956000
_diffrn_orient_matrix_UB_12      -0.0201951000
_diffrn_orient_matrix_UB_13      0.0669392000
_diffrn_orient_matrix_UB_21      0.1619271000
_diffrn_orient_matrix_UB_22      0.0224801000
_diffrn_orient_matrix_UB_23      0.0262431000
_diffrn_orient_matrix_UB_31      -0.0442397000
_diffrn_orient_matrix_UB_32      0.1258222000
_diffrn_orient_matrix_UB_33      -0.0037462000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     39.00  94.00   0.50    0.13    --   47.33-128.00 -15.00  110
  2  ω     54.00  79.00   0.50    0.53    --  113.25-128.00 -15.00   50
  3  ω     47.00  79.00   0.50    0.53    --  113.25-125.00 120.00   64
  4  ω     84.00 109.00   0.50    0.53    --  113.25-125.00 120.00   50
  5  ω     90.00 125.00   0.50    0.53    --  113.25-144.00 174.00   70
  6  ω     50.00 103.00   0.50    0.13    --   47.33-144.00 174.00  106
  7  ω     83.00 109.00   0.50    0.53    --  113.25-125.00  90.00   52
  8  ω     45.00  81.00   0.50    0.53    --  113.25-125.00  90.00   72
  9  ω     59.00 107.00   0.50    0.53    --  113.25-103.00 -21.12   96
 10  ω     81.00 106.00   0.50    0.53    --  113.25 -95.00 -30.00   50
 11  ω     44.00 106.00   0.50    0.53    --  113.25 -95.00   0.00  124
 12  ω     52.00  86.00   0.50    0.53    --  113.25 -95.00 120.00   68
 13  ω     57.00 106.00   0.50    0.53    --  113.25 -95.00-120.00   98
 14  ω     80.00 106.00   0.50    0.53    --  113.25 -95.00-150.00   52
 15  ω     43.00  69.00   0.50    0.53    --  113.25 -95.00-150.00   52
 16  ω     44.00 108.00   0.50    0.53    --  113.25-108.00-177.64  128
 17  ω     75.00 106.00   0.50    0.53    --  113.25 -95.00-180.00   62
 18  ω     46.00 106.00   0.50    0.53    --  113.25 -95.00 -90.00  120
 19  ω     46.00  92.00   0.50    0.53    --  113.25 -95.00 -60.00   92
 20  ω     45.00  73.00   0.50    0.53    --  113.25 -95.00  30.00   56
 21  ω     77.00 106.00   0.50    0.53    --  113.25 -95.00  60.00   58
 22  ω     53.00  98.00   0.50    0.53    --  113.25 -95.00 150.00   90
 23  ω     43.00  69.00   0.50    0.53    --  113.25 -61.00 150.00   52
 24  ω     44.00  72.00   0.50    0.53    --  113.25 -61.00  90.00   56
 25  ω     42.00  68.00   0.50    0.53    --  113.25 -61.00  30.00   52
 26  ω     43.00  71.00   0.50    0.53    --  113.25 -61.00 -60.00   56
 27  ω     44.00  73.00   0.50    0.53    --  113.25 -61.00-150.00   58
 28  ω     46.00  71.00   0.50    0.53    --  113.25 -61.00-180.00   50
 29  ω    100.00 173.00   0.50    0.53    --  113.25  15.00 -60.00  146
 30  ω    110.00 178.00   0.50    0.53    --  113.25  30.00-120.00  136
 31  ω    102.00 157.00   0.50    0.53    --  113.25  30.00  30.00  110
 32  ω    124.00 150.00   0.50    0.53    --  113.25  45.00  60.00   52
 33  ω    104.00 139.00   0.50    0.53    --  113.25  30.00 120.00   70
 34  ω    102.00 170.00   0.50    0.53    --  113.25  45.00 150.00  136
 35  ω    101.00 144.00   0.50    0.53    --  113.25  15.00   0.00   86
 36  ω    100.00 158.00   0.50    0.53    --  113.25  15.00 -30.00  116
 37  ω    106.00 178.00   0.50    0.53    --  113.25  15.00-150.00  144
 38  ω    102.00 127.00   0.50    0.53    --  113.25 144.00-131.00   50
 39  ω    119.00 159.00   0.50    0.53    --  113.25 128.00  59.00   80
 40  ω    -26.00   9.00   0.50    0.13    --   47.33 -19.00   0.00   70
 41  ω   -118.00 -30.00   0.50    0.13    --  -47.33 -77.00-120.00  176
 42  ω   -141.00-116.00   0.50    0.53    --  -91.75-128.00 -15.00   50
 43  ω    -99.00 -73.00   0.50    0.13    --  -47.33-128.00 -15.00   52
 44  ω   -116.00 -67.00   0.50    0.13    --  -47.33-144.00 174.00   98
 45  ω   -131.00-106.00   0.50    0.53    --  -91.75-144.00 174.00   50
 46  ω   -164.00-138.00   0.50    0.53    --  -91.75 -30.00  30.00   52
 47  ω    -49.00 -21.00   0.50    0.53    --  -91.75  45.00-180.00   56
 48  ω    -22.00  28.00   0.50    0.13    --  -47.33  19.00-180.00  100
 49  ω     -8.00  25.00   0.50    0.13    --  -47.33  19.00-150.00   66
 50  ω    -24.00  14.00   0.50    0.13    --  -47.33  19.00   0.00   76
 51  ω    -41.00  23.00   0.50    0.13    --  -47.33  38.00  90.00  128
 52  ω    -74.00 -49.00   0.50    0.53    --  -91.75 128.00  59.00   50
 53  ω    -47.00 -22.00   0.50    0.13    --  -47.33 128.00  59.00   50
 54  ω    -86.00 -61.00   0.50    0.13    --  -47.33 144.00-131.00   50
 55  ω    -86.00 -61.00   0.50    0.53    --  -91.75 144.00-131.00   50
;
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_number            29542
_diffrn_reflns_av_unetI/netI     0.0789
_diffrn_reflns_av_R_equivalents  0.1023
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         2.065
_diffrn_reflns_theta_max         79.883
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.965
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.965
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             9156
_reflns_number_gt                6864
_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 1.171.42.88a (Rigaku OD, 2023)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.88a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.88a (Rigaku OD, 2023)'
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_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)+(0.1756P)²+0.2368P] 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         9156
_refine_ls_number_parameters     600
_refine_ls_number_restraints     8
_refine_ls_R_factor_all          0.1016
_refine_ls_R_factor_gt           0.0860
_refine_ls_wR_factor_ref         0.2716
_refine_ls_wR_factor_gt          0.2464
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_restrained_S_all      1.100
_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
C1 C 0.2968(4) 0.9841(3) 0.78619(18) 0.0533(7) Uani 1 1 d . . . . .
C2 C 0.2120(5) 1.0821(3) 0.7932(2) 0.0600(9) Uani 1 1 d . . . . .
C3 C 0.2203(6) 1.1333(3) 0.8470(2) 0.0726(12) Uani 1 1 d . . . . .
H3 H 0.161914 1.198439 0.851440 0.087 Uiso 1 1 calc R U . . .
C4 C 0.3173(6) 1.0848(4) 0.8933(2) 0.0760(12) Uani 1 1 d . . . . .
C5 C 0.4033(6) 0.9867(4) 0.8886(2) 0.0747(11) Uani 1 1 d . . . . .
H5 H 0.466772 0.954456 0.920976 0.090 Uiso 1 1 calc R U . . .
C6 C 0.3920(5) 0.9381(3) 0.8343(2) 0.0622(9) Uani 1 1 d . . . . .
H6 H 0.450147 0.872661 0.830130 0.075 Uiso 1 1 calc R U . . .
C7 C 0.2885(4) 0.9296(3) 0.72662(19) 0.0551(8) Uani 1 1 d . . . . .
H7 H 0.181401 0.939035 0.710272 0.066 Uiso 1 1 calc R U . . .
C8 C 0.4057(4) 0.9856(3) 0.67866(18) 0.0558(8) Uani 1 1 d . . . . .
H8A H 0.379755 1.065147 0.670150 0.067 Uiso 1 1 calc R U . . .
H8B H 0.511145 0.977587 0.695407 0.067 Uiso 1 1 calc R U . . .
C9 C 0.5278(6) 0.9049(4) 0.5884(2) 0.0690(10) Uani 1 1 d . . . . .
H9 H 0.632220 0.910435 0.599784 0.083 Uiso 1 1 calc R U . . .
C10 C 0.3216(7) 0.8698(5) 0.5383(3) 0.0901(15) Uani 1 1 d . . . . .
H10 H 0.257578 0.845967 0.508485 0.108 Uiso 1 1 calc R U . . .
C11 C 0.2725(6) 0.9143(5) 0.5885(3) 0.0921(16) Uani 1 1 d . . . . .
H11 H 0.168124 0.928440 0.600181 0.111 Uiso 1 1 calc R U . . .
C12 C 0.2018(5) 0.7469(3) 0.7631(3) 0.0815(15) Uani 1 1 d . . . . .
H12A H 0.111953 0.759561 0.735890 0.098 Uiso 1 1 calc R U . . .
H12B H 0.170365 0.767305 0.803685 0.098 Uiso 1 1 calc R U . . .
C13 C 0.2730(5) 0.5590(3) 0.8243(3) 0.0720(11) Uani 1 1 d . . . . .
C14 C 0.2529(4) 0.6260(3) 0.7694(2) 0.0638(10) Uani 1 1 d . . . . .
C15 C 0.2860(5) 0.5646(4) 0.7184(3) 0.0704(10) Uani 1 1 d . . . . .
H15 H 0.280530 0.595658 0.676666 0.084 Uiso 1 1 calc R U . . .
C16 C 0.3268(5) 0.4549(4) 0.7375(3) 0.0792(14) Uani 1 1 d . . . . .
H16 H 0.350877 0.402894 0.710218 0.095 Uiso 1 1 calc R U . . .
C17 C 0.8059(4) 0.3649(3) 0.82348(16) 0.0496(7) Uani 1 1 d . . . . .
C18 C 0.7380(4) 0.2602(3) 0.83469(18) 0.0552(8) Uani 1 1 d . . . . .
C19 C 0.7599(5) 0.1896(3) 0.8899(2) 0.0680(10) Uani 1 1 d . . . . .
H19 H 0.713041 0.119649 0.896818 0.082 Uiso 1 1 calc R U . . .
C20 C 0.8525(6) 0.2253(4) 0.9344(2) 0.0739(11) Uani 1 1 d . . . . .
C21 C 0.9243(6) 0.3269(4) 0.9254(2) 0.0718(10) Uani 1 1 d . . . . .
H21 H 0.988493 0.348646 0.955720 0.086 Uiso 1 1 calc R U . . .
C22 C 0.8995(5) 0.3968(3) 0.87001(19) 0.0602(8) Uani 1 1 d . . . . .
H22 H 0.946334 0.466776 0.863711 0.072 Uiso 1 1 calc R U . . .
C23 C 0.7762(4) 0.4457(2) 0.76409(16) 0.0471(7) Uani 1 1 d . . . . .
H23 H 0.664105 0.444109 0.754046 0.057 Uiso 1 1 calc R U . . .
C24 C 0.8765(4) 0.4150(3) 0.70834(16) 0.0529(7) Uani 1 1 d . . . . .
H24A H 0.987782 0.422639 0.716084 0.063 Uiso 1 1 calc R U . . .
H24B H 0.858705 0.337719 0.702408 0.063 Uiso 1 1 calc R U . . .
C25 C 0.7115(4) 0.4766(3) 0.61620(17) 0.0566(8) Uani 1 1 d . . . . .
H25 H 0.645788 0.415022 0.620622 0.068 Uiso 1 1 calc R U . . .
C26 C 0.8173(6) 0.6369(4) 0.5808(2) 0.0758(11) Uani 1 1 d . . . . .
H26 H 0.836488 0.704971 0.556097 0.091 Uiso 1 1 calc R U . . .
C27 C 0.8984(6) 0.5919(4) 0.6302(2) 0.0749(11) Uani 1 1 d . . . . .
H27 H 0.984511 0.623310 0.646781 0.090 Uiso 1 1 calc R U . . .
C28 C 0.6878(5) 0.6175(3) 0.7967(2) 0.0643(10) Uani 1 1 d . . . . .
C29A C 0.791(3) 0.7533(16) 0.8714(9) 0.066(4) Uani 0.50(3) 1 d . . P . .
C29B C 0.778(3) 0.766(2) 0.8499(11) 0.076(4) Uani 0.50(3) 1 d . . P . .
C30A C 0.7504(9) 0.7393(9) 0.7930(7) 0.055(3) Uiso 0.50(3) 1 d . . P . .
C30B C 0.7448(7) 0.7244(6) 0.8141(5) 0.040(2) Uiso 0.50(3) 1 d . . P . .
C31A C 0.7660(19) 0.8138(13) 0.7652(6) 0.054(3) Uani 0.50(3) 1 d . . P . .
C31B C 0.770(2) 0.8285(18) 0.7415(14) 0.087(6) Uani 0.50(3) 1 d . . P . .
C32A C 0.829(3) 0.9128(18) 0.7874(10) 0.071(4) Uani 0.50(3) 1 d . . P . .
C32B C 0.815(3) 0.914(2) 0.7598(18) 0.102(8) Uani 0.50(3) 1 d . . P . .
N1 N 0.4033(4) 0.9354(2) 0.61996(16) 0.0582(7) Uani 1 1 d . . . . .
N2 N 0.4812(6) 0.8651(3) 0.53804(19) 0.0757(10) Uani 1 1 d . . . . .
N3 N 0.8317(3) 0.4902(2) 0.65261(14) 0.0508(6) Uani 1 1 d . . . . .
N4 N 0.7003(4) 0.5637(3) 0.57323(15) 0.0614(7) Uani 1 1 d . . . . .
O1 O 0.3301(3) 0.81327(17) 0.73754(14) 0.0571(6) Uani 1 1 d . . . . .
O2 O 0.8162(3) 0.55766(17) 0.77049(12) 0.0511(5) Uani 1 1 d . . . . .
O3 O 0.6636(4) 0.8034(2) 0.44592(15) 0.0683(7) Uani 1 1 d . . . . .
O4 O 0.5260(3) 0.6294(2) 0.46985(13) 0.0648(7) Uani 1 1 d . . . . .
O5 O 0.7701(3) 0.6368(2) 0.40979(15) 0.0682(7) Uani 1 1 d . . . . .
O6 O 0.5341(3) 0.7249(2) 0.36441(12) 0.0610(6) Uani 1 1 d . . . . .
O7 O 0.7457(7) 0.1410(4) 0.6280(3) 0.1067(14) Uani 1 1 d . . . . .
O8 O 0.8866(8) 0.9350(6) 0.6165(5) 0.171(3) Uani 1 1 d . . . . .
O9A O 0.902(3) 0.8967(12) 0.535(2) 0.120(10) Uani 0.36(4) 1 d . . P . .
O9B O 0.9338(11) 0.8906(6) 0.4905(11) 0.102(5) Uani 0.64(4) 1 d . . P . .
O10 O 0.0599(5) 0.7059(4) 0.4458(3) 0.1032(13) Uani 1 1 d D . . . .
O11 O 0.2368(4) 0.5955(3) 0.5423(2) 0.0856(10) Uani 1 1 d D . . . .
S1 S 0.32856(15) 0.42430(8) 0.81597(8) 0.0840(4) Uani 1 1 d . . . . .
S2A S 0.8477(13) 0.8871(7) 0.8665(4) 0.0909(16) Uani 0.50(3) 1 d . . P . .
S2B S 0.8469(9) 0.9064(11) 0.8390(14) 0.130(6) Uani 0.50(3) 1 d . . P . .
S3 S 0.62423(9) 0.69876(6) 0.42172(4) 0.0489(2) Uani 1 1 d . . . . .
Cl1 Cl 0.09365(14) 1.14707(8) 0.73364(7) 0.0847(4) Uani 1 1 d . . . . .
Cl2 Cl 0.3334(3) 1.15096(16) 0.95949(8) 0.1173(6) Uani 1 1 d . . . . .
Cl3 Cl 0.2485(3) 0.59659(19) 0.89820(10) 0.1313(7) Uani 1 1 d . . . . .
Cl4 Cl 0.62104(13) 0.21491(8) 0.77857(6) 0.0718(3) Uani 1 1 d . . . . .
Cl5 Cl 0.8786(3) 0.13785(16) 1.00523(8) 0.1194(6) Uani 1 1 d . . . . .
Cl6A Cl 0.7791(13) 0.6670(5) 0.9382(4) 0.104(2) Uani 0.50(3) 1 d . . P . .
Cl6B Cl 0.772(2) 0.6938(18) 0.9229(8) 0.177(5) Uani 0.50(3) 1 d . . P . .
H2N H 0.559(8) 0.835(5) 0.514(3) 0.094(18) Uiso 1 1 d . . . . .
H4N H 0.624(9) 0.581(6) 0.547(3) 0.11(2) Uiso 1 1 d . . . . .
H7A H 0.648(8) 0.174(5) 0.631(3) 0.084(16) Uiso 1 1 d . . . . .
H7B H 0.810(10) 0.193(7) 0.613(4) 0.11(3) Uiso 1 1 d . . . . .
H10A H -0.034(5) 0.675(5) 0.432(3) 0.095(18) Uiso 1 1 d D . . . .
H10B H -0.007(9) 0.764(7) 0.449(8) 0.29(9) Uiso 1 1 d D . . . .
H11A H 0.306(12) 0.623(11) 0.512(4) 0.22(6) Uiso 1 1 d D . . . .
H11B H 0.174(15) 0.585(15) 0.508(4) 0.27(8) Uiso 1 1 d D . . . .
H28A H 0.584(6) 0.615(4) 0.771(2) 0.071(13) Uiso 1 1 d . . . . .
H28B H 0.653(6) 0.580(4) 0.842(3) 0.073(14) 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
C1 C6 1.380(6) . ?
C1 C2 1.388(4) . ?
C1 C7 1.523(5) . ?
C2 C3 1.388(6) . ?
C2 Cl1 1.741(4) . ?
C3 C4 1.371(8) . ?
C3 H3 0.9300 . ?
C4 C5 1.383(7) . ?
C4 Cl2 1.736(5) . ?
C5 C6 1.385(6) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 O1 1.423(3) . ?
C7 C8 1.517(6) . ?
C7 H7 0.9800 . ?
C8 N1 1.475(5) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 N1 1.309(6) . ?
C9 N2 1.319(6) . ?
C9 H9 0.9300 . ?
C10 C11 1.325(8) . ?
C10 N2 1.350(8) . ?
C10 H10 0.9300 . ?
C11 N1 1.360(6) . ?
C11 H11 0.9300 . ?
C12 O1 1.419(5) . ?
C12 C14 1.494(5) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.355(7) . ?
C13 S1 1.705(4) . ?
C13 Cl3 1.721(5) . ?
C14 C15 1.424(6) . ?
C15 C16 1.366(7) . ?
C15 H15 0.9300 . ?
C16 S1 1.686(6) . ?
C16 H16 0.9300 . ?
C17 C18 1.385(5) . ?
C17 C22 1.395(5) . ?
C17 C23 1.525(5) . ?
C18 C19 1.383(6) . ?
C18 Cl4 1.736(4) . ?
C19 C20 1.373(7) . ?
C19 H19 0.9300 . ?
C20 C21 1.365(7) . ?
C20 Cl5 1.754(4) . ?
C21 C22 1.384(6) . ?
C21 H21 0.9300 . ?
C22 H22 0.9300 . ?
C23 O2 1.421(4) . ?
C23 C24 1.534(5) . ?
C23 H23 0.9800 . ?
C24 N3 1.458(4) . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C25 N4 1.306(5) . ?
C25 N3 1.328(5) . ?
C25 H25 0.9300 . ?
C26 C27 1.332(7) . ?
C26 N4 1.368(6) . ?
C26 H26 0.9300 . ?
C27 N3 1.381(5) . ?
C27 H27 0.9300 . ?
C28 O2 1.433(4) . ?
C28 C30B 1.480(8) . ?
C28 C30A 1.559(11) . ?
C28 H28A 1.06(5) . ?
C28 H28B 1.05(5) . ?
C29A Cl6B 1.25(2) . ?
C29A C30B 1.397(19) . ?
C29A Cl6A 1.663(19) . ?
C29A S2A 1.68(2) . ?
C29A C30A 1.77(3) . ?
C29A S2B 1.95(2) . ?
C29B C30B 1.02(3) . ?
C29B C30A 1.34(3) . ?
C29B S2A 1.67(3) . ?
C29B Cl6B 1.69(2) . ?
C29B S2B 1.78(3) . ?
C29B C31A 1.85(2) . ?
C29B Cl6A 2.11(2) . ?
C30A C31A 1.02(2) . ?
C30A C31B 1.45(3) . ?
C30B C31A 1.41(2) . ?
C30B C31B 1.88(3) . ?
C31A C31B 0.52(2) . ?
C31A C32B 1.27(4) . ?
C31A C32A 1.46(3) . ?
C31A S2B 2.20(2) . ?
C31B C32B 1.22(3) . ?
C31B C32A 1.60(4) . ?
C32A C32B 0.61(3) . ?
C32A S2B 1.12(3) . ?
C32A S2A 1.71(2) . ?
C32B S2B 1.73(3) . ?
N2 H2N 0.93(7) . ?
N4 H4N 0.87(8) . ?
O3 S3 1.473(3) . ?
O4 S3 1.491(3) . ?
O5 S3 1.461(3) . ?
O6 S3 1.466(3) . ?
O7 H7A 0.91(7) . ?
O7 H7B 0.86(8) . ?
O9A O9B 1.01(3) . ?
O10 H10A 0.953(18) . ?
O10 H10B 0.90(2) . ?
O11 H11A 0.90(2) . ?
O11 H11B 0.956(18) . ?
S2A S2B 0.61(3) . ?

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
C6 C1 C2 118.2(4) . . ?
C6 C1 C7 120.6(3) . . ?
C2 C1 C7 121.2(3) . . ?
C3 C2 C1 121.7(4) . . ?
C3 C2 Cl1 117.5(3) . . ?
C1 C2 Cl1 120.8(3) . . ?
C4 C3 C2 117.9(3) . . ?
C4 C3 H3 121.0 . . ?
C2 C3 H3 121.0 . . ?
C3 C4 C5 122.5(4) . . ?
C3 C4 Cl2 118.2(3) . . ?
C5 C4 Cl2 119.3(4) . . ?
C4 C5 C6 117.9(5) . . ?
C4 C5 H5 121.0 . . ?
C6 C5 H5 121.0 . . ?
C1 C6 C5 121.8(3) . . ?
C1 C6 H6 119.1 . . ?
C5 C6 H6 119.1 . . ?
O1 C7 C8 107.6(3) . . ?
O1 C7 C1 111.3(3) . . ?
C8 C7 C1 108.9(3) . . ?
O1 C7 H7 109.7 . . ?
C8 C7 H7 109.7 . . ?
C1 C7 H7 109.7 . . ?
N1 C8 C7 111.2(3) . . ?
N1 C8 H8A 109.4 . . ?
C7 C8 H8A 109.4 . . ?
N1 C8 H8B 109.4 . . ?
C7 C8 H8B 109.4 . . ?
H8A C8 H8B 108.0 . . ?
N1 C9 N2 109.1(4) . . ?
N1 C9 H9 125.5 . . ?
N2 C9 H9 125.5 . . ?
C11 C10 N2 107.8(4) . . ?
C11 C10 H10 126.1 . . ?
N2 C10 H10 126.1 . . ?
C10 C11 N1 107.2(5) . . ?
C10 C11 H11 126.4 . . ?
N1 C11 H11 126.4 . . ?
O1 C12 C14 108.6(3) . . ?
O1 C12 H12A 110.0 . . ?
C14 C12 H12A 110.0 . . ?
O1 C12 H12B 110.0 . . ?
C14 C12 H12B 110.0 . . ?
H12A C12 H12B 108.4 . . ?
C14 C13 S1 113.8(3) . . ?
C14 C13 Cl3 126.9(3) . . ?
S1 C13 Cl3 119.3(3) . . ?
C13 C14 C15 110.3(4) . . ?
C13 C14 C12 125.0(4) . . ?
C15 C14 C12 124.7(5) . . ?
C16 C15 C14 112.5(5) . . ?
C16 C15 H15 123.7 . . ?
C14 C15 H15 123.7 . . ?
C15 C16 S1 112.6(3) . . ?
C15 C16 H16 123.7 . . ?
S1 C16 H16 123.7 . . ?
C18 C17 C22 117.5(3) . . ?
C18 C17 C23 122.3(3) . . ?
C22 C17 C23 120.2(3) . . ?
C19 C18 C17 121.9(4) . . ?
C19 C18 Cl4 118.3(3) . . ?
C17 C18 Cl4 119.8(3) . . ?
C20 C19 C18 118.3(4) . . ?
C20 C19 H19 120.8 . . ?
C18 C19 H19 120.8 . . ?
C21 C20 C19 122.2(4) . . ?
C21 C20 Cl5 118.8(4) . . ?
C19 C20 Cl5 118.9(4) . . ?
C20 C21 C22 118.5(4) . . ?
C20 C21 H21 120.8 . . ?
C22 C21 H21 120.7 . . ?
C21 C22 C17 121.6(4) . . ?
C21 C22 H22 119.2 . . ?
C17 C22 H22 119.2 . . ?
O2 C23 C17 112.2(3) . . ?
O2 C23 C24 105.4(3) . . ?
C17 C23 C24 112.1(2) . . ?
O2 C23 H23 109.0 . . ?
C17 C23 H23 109.0 . . ?
C24 C23 H23 109.0 . . ?
N3 C24 C23 108.7(2) . . ?
N3 C24 H24A 110.0 . . ?
C23 C24 H24A 110.0 . . ?
N3 C24 H24B 110.0 . . ?
C23 C24 H24B 110.0 . . ?
H24A C24 H24B 108.3 . . ?
N4 C25 N3 109.1(3) . . ?
N4 C25 H25 125.4 . . ?
N3 C25 H25 125.4 . . ?
C27 C26 N4 106.7(4) . . ?
C27 C26 H26 126.6 . . ?
N4 C26 H26 126.6 . . ?
C26 C27 N3 107.7(4) . . ?
C26 C27 H27 126.1 . . ?
N3 C27 H27 126.1 . . ?
O2 C28 C30B 109.7(4) . . ?
O2 C28 C30A 103.3(4) . . ?
C30B C28 C30A 17.4(4) . . ?
O2 C28 H28A 111(3) . . ?
C30B C28 H28A 122(3) . . ?
C30A C28 H28A 112(3) . . ?
O2 C28 H28B 113(3) . . ?
C30B C28 H28B 98(3) . . ?
C30A C28 H28B 115(3) . . ?
H28A C28 H28B 103(4) . . ?
Cl6B C29A C30B 125.0(18) . . ?
Cl6B C29A Cl6A 5.0(10) . . ?
C30B C29A Cl6A 123.6(15) . . ?
Cl6B C29A S2A 121.5(14) . . ?
C30B C29A S2A 112.8(14) . . ?
Cl6A C29A S2A 123.5(9) . . ?
Cl6B C29A C30A 135.4(17) . . ?
C30B C29A C30A 10.5(5) . . ?
Cl6A C29A C30A 133.8(14) . . ?
S2A C29A C30A 102.7(12) . . ?
Cl6B C29A S2B 138.8(13) . . ?
C30B C29A S2B 95.4(10) . . ?
Cl6A C29A S2B 140.9(10) . . ?
S2A C29A S2B 17.4(8) . . ?
C30A C29A S2B 85.3(9) . . ?
C30B C29B C30A 17.0(8) . . ?
C30B C29B S2A 144(2) . . ?
C30A C29B S2A 126.6(19) . . ?
C30B C29B Cl6B 117(2) . . ?
C30A C29B Cl6B 134.0(19) . . ?
S2A C29B Cl6B 99.2(13) . . ?
C30B C29B S2B 123.6(19) . . ?
C30A C29B S2B 106.7(15) . . ?
S2A C29B S2B 19.9(9) . . ?
Cl6B C29B S2B 119.1(12) . . ?
C30B C29B C31A 49.3(15) . . ?
C30A C29B C31A 32.6(12) . . ?
S2A C29B C31A 94.2(14) . . ?
Cl6B C29B C31A 166.5(18) . . ?
S2B C29B C31A 74.3(13) . . ?
C30B C29B Cl6A 115(2) . . ?
C30A C29B Cl6A 131.2(17) . . ?
S2A C29B Cl6A 101.8(9) . . ?
Cl6B C29B Cl6A 4.0(7) . . ?
S2B C29B Cl6A 121.6(10) . . ?
C31A C29B Cl6A 163.8(15) . . ?
C31A C30A C29B 102.5(16) . . ?
C31A C30A C31B 13.8(18) . . ?
C29B C30A C31B 116.1(16) . . ?
C31A C30A C28 145.3(14) . . ?
C29B C30A C28 111.4(16) . . ?
C31B C30A C28 132.3(18) . . ?
C31A C30A C29A 110.4(13) . . ?
C29B C30A C29A 8.2(15) . . ?
C31B C30A C29A 123.8(14) . . ?
C28 C30A C29A 103.8(13) . . ?
C29B C30B C29A 14.7(19) . . ?
C29B C30B C31A 97.4(19) . . ?
C29A C30B C31A 111.7(12) . . ?
C29B C30B C28 145.7(19) . . ?
C29A C30B C28 131.3(13) . . ?
C31A C30B C28 116.9(9) . . ?
C29B C30B C31B 105.1(18) . . ?
C29A C30B C31B 119.3(13) . . ?
C31A C30B C31B 7.9(14) . . ?
C28 C30B C31B 109.3(13) . . ?
C31B C31A C30A 138(5) . . ?
C31B C31A C32B 72(4) . . ?
C30A C31A C32B 148(2) . . ?
C31B C31A C30B 150(5) . . ?
C30A C31A C30B 12.0(7) . . ?
C32B C31A C30B 136.6(19) . . ?
C31B C31A C32A 97(5) . . ?
C30A C31A C32A 123.3(16) . . ?
C32B C31A C32A 24.6(17) . . ?
C30B C31A C32A 112.0(13) . . ?
C31B C31A C29B 173(5) . . ?
C30A C31A C29B 44.9(12) . . ?
C32B C31A C29B 103(2) . . ?
C30B C31A C29B 33.3(10) . . ?
C32A C31A C29B 78.8(14) . . ?
C31B C31A S2B 124(5) . . ?
C30A C31A S2B 96.1(10) . . ?
C32B C31A S2B 51.9(14) . . ?
C30B C31A S2B 84.7(8) . . ?
C32A C31A S2B 27.3(10) . . ?
C29B C31A S2B 51.4(11) . . ?
C31A C31B C32B 84(5) . . ?
C31A C31B C30A 28(3) . . ?
C32B C31B C30A 111(2) . . ?
C31A C31B C32A 64(5) . . ?
C32B C31B C32A 19.4(19) . . ?
C30A C31B C32A 91.6(18) . . ?
C31A C31B C30B 22(4) . . ?
C32B C31B C30B 105(2) . . ?
C30A C31B C30B 6.1(6) . . ?
C32A C31B C30B 85.8(14) . . ?
C32B C32A S2B 176(6) . . ?
C32B C32A C31A 60(4) . . ?
S2B C32A C31A 116(2) . . ?
C32B C32A C31B 42(4) . . ?
S2B C32A C31B 135(2) . . ?
C31A C32A C31B 18.7(7) . . ?
C32B C32A S2A 169(6) . . ?
S2B C32A S2A 6.9(9) . . ?
C31A C32A S2A 109.2(15) . . ?
C31B C32A S2A 127.8(16) . . ?
C32A C32B C31B 119(6) . . ?
C32A C32B C31A 95(5) . . ?
C31B C32B C31A 23.9(13) . . ?
C32A C32B S2B 3(4) . . ?
C31B C32B S2B 116(2) . . ?
C31A C32B S2B 92.8(18) . . ?
C9 N1 C11 108.0(4) . . ?
C9 N1 C8 125.7(3) . . ?
C11 N1 C8 126.3(4) . . ?
C9 N2 C10 107.9(4) . . ?
C9 N2 H2N 117(4) . . ?
C10 N2 H2N 135(4) . . ?
C25 N3 C27 107.2(3) . . ?
C25 N3 C24 125.9(3) . . ?
C27 N3 C24 126.7(3) . . ?
C25 N4 C26 109.2(3) . . ?
C25 N4 H4N 128(5) . . ?
C26 N4 H4N 122(5) . . ?
C12 O1 C7 112.2(3) . . ?
C23 O2 C28 112.0(3) . . ?
H7A O7 H7B 107(7) . . ?
H10A O10 H10B 82(4) . . ?
H11A O11 H11B 83(4) . . ?
C16 S1 C13 90.8(2) . . ?
S2B S2A C29B 90.7(17) . . ?
S2B S2A C29A 107.0(16) . . ?
C29B S2A C29A 16.5(7) . . ?
S2B S2A C32A 12.9(15) . . ?
C29B S2A C32A 77.8(11) . . ?
C29A S2A C32A 94.2(9) . . ?
S2A S2B C32A 160(2) . . ?
S2A S2B C32B 158.9(19) . . ?
C32A S2B C32B 1(2) . . ?
S2A S2B C29B 69.4(16) . . ?
C32A S2B C29B 90.8(14) . . ?
C32B S2B C29B 89.6(11) . . ?
S2A S2B C29A 55.6(15) . . ?
C32A S2B C29A 104.6(14) . . ?
C32B S2B C29A 103.4(10) . . ?
C29B S2B C29A 14.0(5) . . ?
S2A S2B C31A 123.6(17) . . ?
C32A S2B C31A 36.6(13) . . ?
C32B S2B C31A 35.4(10) . . ?
C29B S2B C31A 54.2(6) . . ?
C29A S2B C31A 68.1(5) . . ?
O5 S3 O6 110.74(18) . . ?
O5 S3 O3 109.16(18) . . ?
O6 S3 O3 109.86(17) . . ?
O5 S3 O4 109.26(17) . . ?
O6 S3 O4 109.18(16) . . ?
O3 S3 O4 108.60(18) . . ?
C29A Cl6A C29B 5.6(12) . . ?
C29A Cl6B C29B 7.1(16) . . ?

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
C6 C1 C2 C3 -0.5(6) . . . . ?
C7 C1 C2 C3 -179.2(4) . . . . ?
C6 C1 C2 Cl1 178.3(3) . . . . ?
C7 C1 C2 Cl1 -0.5(5) . . . . ?
C1 C2 C3 C4 0.9(6) . . . . ?
Cl1 C2 C3 C4 -177.9(3) . . . . ?
C2 C3 C4 C5 -1.3(7) . . . . ?
C2 C3 C4 Cl2 177.8(3) . . . . ?
C3 C4 C5 C6 1.3(8) . . . . ?
Cl2 C4 C5 C6 -177.8(3) . . . . ?
C2 C1 C6 C5 0.5(6) . . . . ?
C7 C1 C6 C5 179.2(4) . . . . ?
C4 C5 C6 C1 -0.8(7) . . . . ?
C6 C1 C7 O1 24.1(5) . . . . ?
C2 C1 C7 O1 -157.2(3) . . . . ?
C6 C1 C7 C8 -94.4(4) . . . . ?
C2 C1 C7 C8 84.3(4) . . . . ?
O1 C7 C8 N1 58.8(4) . . . . ?
C1 C7 C8 N1 179.6(3) . . . . ?
N2 C10 C11 N1 -1.0(7) . . . . ?
S1 C13 C14 C15 -0.6(5) . . . . ?
Cl3 C13 C14 C15 179.3(3) . . . . ?
S1 C13 C14 C12 178.8(3) . . . . ?
Cl3 C13 C14 C12 -1.2(7) . . . . ?
O1 C12 C14 C13 112.1(5) . . . . ?
O1 C12 C14 C15 -68.5(6) . . . . ?
C13 C14 C15 C16 0.9(5) . . . . ?
C12 C14 C15 C16 -178.5(4) . . . . ?
C14 C15 C16 S1 -0.8(5) . . . . ?
C22 C17 C18 C19 0.6(5) . . . . ?
C23 C17 C18 C19 -177.0(3) . . . . ?
C22 C17 C18 Cl4 -179.7(3) . . . . ?
C23 C17 C18 Cl4 2.8(4) . . . . ?
C17 C18 C19 C20 -0.3(6) . . . . ?
Cl4 C18 C19 C20 180.0(3) . . . . ?
C18 C19 C20 C21 -0.8(7) . . . . ?
C18 C19 C20 Cl5 178.9(3) . . . . ?
C19 C20 C21 C22 1.5(7) . . . . ?
Cl5 C20 C21 C22 -178.2(4) . . . . ?
C20 C21 C22 C17 -1.1(7) . . . . ?
C18 C17 C22 C21 0.1(6) . . . . ?
C23 C17 C22 C21 177.8(4) . . . . ?
C18 C17 C23 O2 162.1(3) . . . . ?
C22 C17 C23 O2 -15.4(4) . . . . ?
C18 C17 C23 C24 -79.4(4) . . . . ?
C22 C17 C23 C24 103.0(4) . . . . ?
O2 C23 C24 N3 -62.3(3) . . . . ?
C17 C23 C24 N3 175.3(3) . . . . ?
N4 C26 C27 N3 0.6(6) . . . . ?
C30B C29B C30A C31A 168(3) . . . . ?
S2A C29B C30A C31A -8(2) . . . . ?
Cl6B C29B C30A C31A 177(2) . . . . ?
S2B C29B C30A C31A -6.8(16) . . . . ?
Cl6A C29B C30A C31A -178.8(17) . . . . ?
C30B C29B C30A C31B 171(3) . . . . ?
S2A C29B C30A C31B -5(2) . . . . ?
Cl6B C29B C30A C31B 179.9(19) . . . . ?
S2B C29B C30A C31B -4.2(18) . . . . ?
C31A C29B C30A C31B 2.5(17) . . . . ?
Cl6A C29B C30A C31B -176.3(16) . . . . ?
C30B C29B C30A C28 -5(2) . . . . ?
S2A C29B C30A C28 179.4(13) . . . . ?
Cl6B C29B C30A C28 5(3) . . . . ?
S2B C29B C30A C28 -179.4(8) . . . . ?
C31A C29B C30A C28 -172.6(14) . . . . ?
Cl6A C29B C30A C28 9(2) . . . . ?
C30B C29B C30A C29A -29(11) . . . . ?
S2A C29B C30A C29A 155(13) . . . . ?
Cl6B C29B C30A C29A -20(10) . . . . ?
S2B C29B C30A C29A 156(13) . . . . ?
C31A C29B C30A C29A 163(12) . . . . ?
Cl6A C29B C30A C29A -16(10) . . . . ?
O2 C28 C30A C31A 82.2(19) . . . . ?
C30B C28 C30A C31A -164(3) . . . . ?
O2 C28 C30A C29B -110.5(11) . . . . ?
C30B C28 C30A C29B 3.2(14) . . . . ?
O2 C28 C30A C31B 75.4(13) . . . . ?
C30B C28 C30A C31B -171(2) . . . . ?
O2 C28 C30A C29A -107.0(8) . . . . ?
C30B C28 C30A C29A 6.6(14) . . . . ?
Cl6B C29A C30A C31A 170(2) . . . . ?
C30B C29A C30A C31A 163(3) . . . . ?
Cl6A C29A C30A C31A 176.6(17) . . . . ?
S2A C29A C30A C31A -2.5(16) . . . . ?
S2B C29A C30A C31A -3.1(13) . . . . ?
Cl6B C29A C30A C29B 152(14) . . . . ?
C30B C29A C30A C29B 145(13) . . . . ?
Cl6A C29A C30A C29B 159(13) . . . . ?
S2A C29A C30A C29B -20(11) . . . . ?
S2B C29A C30A C29B -21(11) . . . . ?
Cl6B C29A C30A C31B 173(2) . . . . ?
C30B C29A C30A C31B 166(3) . . . . ?
Cl6A C29A C30A C31B -179.9(16) . . . . ?
S2A C29A C30A C31B 1.0(17) . . . . ?
S2B C29A C30A C31B 0.4(15) . . . . ?
Cl6B C29A C30A C28 -4(2) . . . . ?
C30B C29A C30A C28 -12(2) . . . . ?
Cl6A C29A C30A C28 2.2(19) . . . . ?
S2A C29A C30A C28 -176.9(9) . . . . ?
S2B C29A C30A C28 -177.5(6) . . . . ?
C30A C29B C30B C29A 160(8) . . . . ?
S2A C29B C30B C29A 165(11) . . . . ?
Cl6B C29B C30B C29A -13(7) . . . . ?
S2B C29B C30B C29A 166(10) . . . . ?
C31A C29B C30B C29A 168(8) . . . . ?
Cl6A C29B C30B C29A -9(7) . . . . ?
C30A C29B C30B C31A -8.5(19) . . . . ?
S2A C29B C30B C31A -3(3) . . . . ?
Cl6B C29B C30B C31A 179.1(16) . . . . ?
S2B C29B C30B C31A -2.5(19) . . . . ?
Cl6A C29B C30B C31A -177.6(13) . . . . ?
C30A C29B C30B C28 172(4) . . . . ?
S2A C29B C30B C28 177.4(14) . . . . ?
Cl6B C29B C30B C28 -1(3) . . . . ?
S2B C29B C30B C28 177.9(8) . . . . ?
C31A C29B C30B C28 -180(2) . . . . ?
Cl6A C29B C30B C28 3(3) . . . . ?
C30A C29B C30B C31B -6.8(18) . . . . ?
S2A C29B C30B C31B -1(3) . . . . ?
Cl6B C29B C30B C31B -179.2(14) . . . . ?
S2B C29B C30B C31B -1(2) . . . . ?
C31A C29B C30B C31B 1.7(12) . . . . ?
Cl6A C29B C30B C31B -175.9(12) . . . . ?
Cl6B C29A C30B C29B 161(10) . . . . ?
Cl6A C29A C30B C29B 167(9) . . . . ?
S2A C29A C30B C29B -9(7) . . . . ?
C30A C29A C30B C29B -25(9) . . . . ?
S2B C29A C30B C29B -11(8) . . . . ?
Cl6B C29A C30B C31A 173.7(17) . . . . ?
Cl6A C29A C30B C31A 179.5(13) . . . . ?
S2A C29A C30B C31A 3.2(17) . . . . ?
C30A C29A C30B C31A -12(2) . . . . ?
S2B C29A C30B C31A 1.7(13) . . . . ?
Cl6B C29A C30B C28 -10(3) . . . . ?
Cl6A C29A C30B C28 -4(2) . . . . ?
S2A C29A C30B C28 179.7(7) . . . . ?
C30A C29A C30B C28 164(3) . . . . ?
S2B C29A C30B C28 178.2(6) . . . . ?
Cl6B C29A C30B C31B 176.1(16) . . . . ?
Cl6A C29A C30B C31B -178.1(12) . . . . ?
S2A C29A C30B C31B 5.6(18) . . . . ?
C30A C29A C30B C31B -10(2) . . . . ?
S2B C29A C30B C31B 4.1(14) . . . . ?
O2 C28 C30B C29B -102(2) . . . . ?
C30A C28 C30B C29B -173(3) . . . . ?
O2 C28 C30B C29A -97.9(13) . . . . ?
C30A C28 C30B C29A -169(2) . . . . ?
O2 C28 C30B C31A 78.4(8) . . . . ?
C30A C28 C30B C31A 7.2(13) . . . . ?
O2 C28 C30B C31B 76.6(8) . . . . ?
C30A C28 C30B C31B 5.4(14) . . . . ?
C29B C30A C31A C31B 170(6) . . . . ?
C28 C30A C31A C31B -22(8) . . . . ?
C29A C30A C31A C31B 168(6) . . . . ?
C29B C30A C31A C32B 12(4) . . . . ?
C31B C30A C31A C32B -158(9) . . . . ?
C28 C30A C31A C32B -180(3) . . . . ?
C29A C30A C31A C32B 10(4) . . . . ?
C29B C30A C31A C30B -12(3) . . . . ?
C31B C30A C31A C30B 177(6) . . . . ?
C28 C30A C31A C30B 156(4) . . . . ?
C29A C30A C31A C30B -15(3) . . . . ?
C29B C30A C31A C32A 8(2) . . . . ?
C31B C30A C31A C32A -162(8) . . . . ?
C28 C30A C31A C32A 176.3(14) . . . . ?
C29A C30A C31A C32A 6(2) . . . . ?
C31B C30A C31A C29B -170(6) . . . . ?
C28 C30A C31A C29B 168(2) . . . . ?
C29A C30A C31A C29B -2.6(16) . . . . ?
C29B C30A C31A S2B 5.3(13) . . . . ?
C31B C30A C31A S2B -165(7) . . . . ?
C28 C30A C31A S2B 173.2(14) . . . . ?
C29A C30A C31A S2B 2.8(12) . . . . ?
C29B C30B C31A C31B 168(9) . . . . ?
C29A C30B C31A C31B 164(8) . . . . ?
C28 C30B C31A C31B -13(9) . . . . ?
C29B C30B C31A C30A 164(3) . . . . ?
C29A C30B C31A C30A 161(3) . . . . ?
C28 C30B C31A C30A -16(3) . . . . ?
C31B C30B C31A C30A -4(8) . . . . ?
C29B C30B C31A C32B 3(3) . . . . ?
C29A C30B C31A C32B 0(3) . . . . ?
C28 C30B C31A C32B -177(2) . . . . ?
C31B C30B C31A C32B -165(10) . . . . ?
C29B C30B C31A C32A 2.7(18) . . . . ?
C29A C30B C31A C32A -0.5(17) . . . . ?
C28 C30B C31A C32A -177.6(11) . . . . ?
C31B C30B C31A C32A -165(9) . . . . ?
C29A C30B C31A C29B -3(2) . . . . ?
C28 C30B C31A C29B 179.8(15) . . . . ?
C31B C30B C31A C29B -168(9) . . . . ?
C29B C30B C31A S2B 1.7(13) . . . . ?
C29A C30B C31A S2B -1.5(11) . . . . ?
C28 C30B C31A S2B -178.6(5) . . . . ?
C31B C30B C31A S2B -166(9) . . . . ?
C30B C29B C31A C30A -4.6(10) . . . . ?
S2A C29B C31A C30A 173.6(18) . . . . ?
Cl6B C29B C31A C30A -8(6) . . . . ?
S2B C29B C31A C30A 173.2(16) . . . . ?
Cl6A C29B C31A C30A 3(5) . . . . ?
C30B C29B C31A C32B -178(2) . . . . ?
C30A C29B C31A C32B -173(2) . . . . ?
S2A C29B C31A C32B 0.2(19) . . . . ?
Cl6B C29B C31A C32B 179(6) . . . . ?
S2B C29B C31A C32B -0.1(16) . . . . ?
Cl6A C29B C31A C32B -170(5) . . . . ?
C30A C29B C31A C30B 4.6(10) . . . . ?
S2A C29B C31A C30B 178.2(19) . . . . ?
Cl6B C29B C31A C30B -3(6) . . . . ?
S2B C29B C31A C30B 177.9(17) . . . . ?
Cl6A C29B C31A C30B 8(4) . . . . ?
C30B C29B C31A C32A -177.5(17) . . . . ?
C30A C29B C31A C32A -172.9(18) . . . . ?
S2A C29B C31A C32A 0.7(13) . . . . ?
Cl6B C29B C31A C32A 179(7) . . . . ?
S2B C29B C31A C32A 0.4(11) . . . . ?
Cl6A C29B C31A C32A -170(5) . . . . ?
C30B C29B C31A S2B -177.9(17) . . . . ?
C30A C29B C31A S2B -173.2(16) . . . . ?
S2A C29B C31A S2B 0.3(7) . . . . ?
Cl6B C29B C31A S2B 179(7) . . . . ?
Cl6A C29B C31A S2B -170(5) . . . . ?
C30A C31A C31B C32B -168(5) . . . . ?
C30B C31A C31B C32B -169(7) . . . . ?
C32A C31A C31B C32B -3(3) . . . . ?
S2B C31A C31B C32B -6(4) . . . . ?
C32B C31A C31B C30A 168(5) . . . . ?
C30B C31A C31B C30A -1(2) . . . . ?
C32A C31A C31B C30A 165(7) . . . . ?
S2B C31A C31B C30A 162(8) . . . . ?
C30A C31A C31B C32A -165(7) . . . . ?
C32B C31A C31B C32A 3(3) . . . . ?
C30B C31A C31B C32A -166(9) . . . . ?
S2B C31A C31B C32A -3(2) . . . . ?
C30A C31A C31B C30B 1(2) . . . . ?
C32B C31A C31B C30B 169(7) . . . . ?
C32A C31A C31B C30B 166(9) . . . . ?
S2B C31A C31B C30B 163(10) . . . . ?
C29B C30A C31B C31A -10(7) . . . . ?
C28 C30A C31B C31A 163(6) . . . . ?
C29A C30A C31B C31A -14(7) . . . . ?
C31A C30A C31B C32B 13(6) . . . . ?
C29B C30A C31B C32B 2(3) . . . . ?
C28 C30A C31B C32B 176.2(17) . . . . ?
C29A C30A C31B C32B -1(3) . . . . ?
C31A C30A C31B C32A 14(6) . . . . ?
C29B C30A C31B C32A 3.1(18) . . . . ?
C28 C30A C31B C32A 177.0(10) . . . . ?
C29A C30A C31B C32A -0.2(18) . . . . ?
C31A C30A C31B C30B -4(9) . . . . ?
C29B C30A C31B C30B -14(4) . . . . ?
C28 C30A C31B C30B 159(5) . . . . ?
C29A C30A C31B C30B -18(4) . . . . ?
C29B C30B C31B C31A -13(9) . . . . ?
C29A C30B C31B C31A -17(9) . . . . ?
C28 C30B C31B C31A 168(8) . . . . ?
C29B C30B C31B C32B -1(2) . . . . ?
C29A C30B C31B C32B -5(2) . . . . ?
C31A C30B C31B C32B 11(8) . . . . ?
C28 C30B C31B C32B 179.4(17) . . . . ?
C29B C30B C31B C30A 162(5) . . . . ?
C29A C30B C31B C30A 158(5) . . . . ?
C31A C30B C31B C30A 175(11) . . . . ?
C28 C30B C31B C30A -17(4) . . . . ?
C29B C30B C31B C32A 0.0(17) . . . . ?
C29A C30B C31B C32A -3.9(16) . . . . ?
C31A C30B C31B C32A 13(8) . . . . ?
C28 C30B C31B C32A -179.2(10) . . . . ?
C31B C31A C32A C32B 7(6) . . . . ?
C30A C31A C32A C32B 175(5) . . . . ?
C30B C31A C32A C32B 180(5) . . . . ?
C29B C31A C32A C32B -179(5) . . . . ?
S2B C31A C32A C32B -178(6) . . . . ?
C31B C31A C32A S2B -175(4) . . . . ?
C30A C31A C32A S2B -7(3) . . . . ?
C32B C31A C32A S2B 178(6) . . . . ?
C30B C31A C32A S2B -2(2) . . . . ?
C29B C31A C32A S2B -0.7(18) . . . . ?
C30A C31A C32A C31B 168(5) . . . . ?
C32B C31A C32A C31B -7(6) . . . . ?
C30B C31A C32A C31B 173(4) . . . . ?
C29B C31A C32A C31B 174(4) . . . . ?
S2B C31A C32A C31B 175(4) . . . . ?
C31B C31A C32A S2A -175(4) . . . . ?
C30A C31A C32A S2A -7(2) . . . . ?
C32B C31A C32A S2A 178(6) . . . . ?
C30B C31A C32A S2A -2.2(18) . . . . ?
C29B C31A C32A S2A -0.8(13) . . . . ?
S2B C31A C32A S2A -0.1(10) . . . . ?
C31A C31B C32A C32B -171(8) . . . . ?
C30A C31B C32A C32B -178(6) . . . . ?
C30B C31B C32A C32B -176(6) . . . . ?
C31A C31B C32A S2B 7(5) . . . . ?
C32B C31B C32A S2B 177(8) . . . . ?
C30A C31B C32A S2B 0(3) . . . . ?
C30B C31B C32A S2B 1(3) . . . . ?
C32B C31B C32A C31A 171(8) . . . . ?
C30A C31B C32A C31A -7(3) . . . . ?
C30B C31B C32A C31A -5(3) . . . . ?
C31A C31B C32A S2A 6(4) . . . . ?
C32B C31B C32A S2A 177(7) . . . . ?
C30A C31B C32A S2A -1(2) . . . . ?
C30B C31B C32A S2A 1.0(19) . . . . ?
C31A C32A C32B C31B -3(3) . . . . ?
S2A C32A C32B C31B -13(31) . . . . ?
C31B C32A C32B C31A 3(3) . . . . ?
S2A C32A C32B C31A -10(29) . . . . ?
C31A C32A C32B S2B 24(83) . . . . ?
C31B C32A C32B S2B 28(85) . . . . ?
S2A C32A C32B S2B 15(56) . . . . ?
C31A C31B C32B C32A 8(7) . . . . ?
C30A C31B C32B C32A 2(7) . . . . ?
C30B C31B C32B C32A 4(6) . . . . ?
C30A C31B C32B C31A -6(3) . . . . ?
C32A C31B C32B C31A -8(7) . . . . ?
C30B C31B C32B C31A -4(3) . . . . ?
C31A C31B C32B S2B 7(4) . . . . ?
C30A C31B C32B S2B 1(3) . . . . ?
C32A C31B C32B S2B -1(4) . . . . ?
C30B C31B C32B S2B 3(2) . . . . ?
C31B C31A C32B C32A -173(6) . . . . ?
C30A C31A C32B C32A -8(7) . . . . ?
C30B C31A C32B C32A 0(6) . . . . ?
C29B C31A C32B C32A 1(5) . . . . ?
S2B C31A C32B C32A 1(4) . . . . ?
C30A C31A C32B C31B 165(6) . . . . ?
C30B C31A C32B C31B 172(5) . . . . ?
C32A C31A C32B C31B 173(6) . . . . ?
C29B C31A C32B C31B 174(4) . . . . ?
S2B C31A C32B C31B 174(4) . . . . ?
C31B C31A C32B S2B -174(4) . . . . ?
C30A C31A C32B S2B -9(4) . . . . ?
C30B C31A C32B S2B -2(3) . . . . ?
C32A C31A C32B S2B -1(4) . . . . ?
C29B C31A C32B S2B 0.1(16) . . . . ?
N2 C9 N1 C11 0.0(6) . . . . ?
N2 C9 N1 C8 -179.0(4) . . . . ?
C10 C11 N1 C9 0.6(7) . . . . ?
C10 C11 N1 C8 179.7(4) . . . . ?
C7 C8 N1 C9 -133.5(4) . . . . ?
C7 C8 N1 C11 47.7(6) . . . . ?
N1 C9 N2 C10 -0.6(6) . . . . ?
C11 C10 N2 C9 1.0(7) . . . . ?
N4 C25 N3 C27 -0.2(4) . . . . ?
N4 C25 N3 C24 175.8(3) . . . . ?
C26 C27 N3 C25 -0.3(6) . . . . ?
C26 C27 N3 C24 -176.2(4) . . . . ?
C23 C24 N3 C25 -84.3(4) . . . . ?
C23 C24 N3 C27 90.8(5) . . . . ?
N3 C25 N4 C26 0.6(5) . . . . ?
C27 C26 N4 C25 -0.8(6) . . . . ?
C14 C12 O1 C7 176.6(4) . . . . ?
C8 C7 O1 C12 -158.9(4) . . . . ?
C1 C7 O1 C12 81.9(4) . . . . ?
C17 C23 O2 C28 -86.7(4) . . . . ?
C24 C23 O2 C28 151.0(3) . . . . ?
C30B C28 O2 C23 168.7(5) . . . . ?
C30A C28 O2 C23 -174.4(6) . . . . ?
C15 C16 S1 C13 0.4(4) . . . . ?
C14 C13 S1 C16 0.2(4) . . . . ?
Cl3 C13 S1 C16 -179.8(3) . . . . ?
C30B C29B S2A S2B 1(4) . . . . ?
C30A C29B S2A S2B 3(3) . . . . ?
Cl6B C29B S2A S2B 179.4(19) . . . . ?
C31A C29B S2A S2B -1.0(19) . . . . ?
Cl6A C29B S2A S2B 176.3(18) . . . . ?
C30B C29B S2A C29A -169(8) . . . . ?
C30A C29B S2A C29A -167(6) . . . . ?
Cl6B C29B S2A C29A 9(4) . . . . ?
S2B C29B S2A C29A -170(5) . . . . ?
C31A C29B S2A C29A -171(6) . . . . ?
Cl6A C29B S2A C29A 6(4) . . . . ?
C30B C29B S2A C32A 2(3) . . . . ?
C30A C29B S2A C32A 3.7(18) . . . . ?
Cl6B C29B S2A C32A 179.8(14) . . . . ?
S2B C29B S2A C32A 0.3(16) . . . . ?
C31A C29B S2A C32A -0.6(11) . . . . ?
Cl6A C29B S2A C32A 176.7(13) . . . . ?
Cl6B C29A S2A S2B -176(2) . . . . ?
C30B C29A S2A S2B -5(2) . . . . ?
Cl6A C29A S2A S2B 179(2) . . . . ?
C30A C29A S2A S2B -2(2) . . . . ?
Cl6B C29A S2A C29B -166(6) . . . . ?
C30B C29A S2A C29B 5(4) . . . . ?
Cl6A C29A S2A C29B -171(6) . . . . ?
C30A C29A S2A C29B 8(4) . . . . ?
S2B C29A S2A C29B 10(5) . . . . ?
Cl6B C29A S2A C32A -174.8(19) . . . . ?
C30B C29A S2A C32A -3.9(16) . . . . ?
Cl6A C29A S2A C32A 179.7(15) . . . . ?
C30A C29A S2A C32A -1.0(13) . . . . ?
S2B C29A S2A C32A 1.0(17) . . . . ?
C32B C32A S2A S2B -172(31) . . . . ?
C31A C32A S2A S2B 179(7) . . . . ?
C31B C32A S2A S2B 177(8) . . . . ?
C32B C32A S2A C29B 10(27) . . . . ?
S2B C32A S2A C29B -178(7) . . . . ?
C31A C32A S2A C29B 0.8(14) . . . . ?
C31B C32A S2A C29B -1.3(19) . . . . ?
C32B C32A S2A C29A 12(28) . . . . ?
S2B C32A S2A C29A -176(7) . . . . ?
C31A C32A S2A C29A 3.5(16) . . . . ?
C31B C32A S2A C29A 1(2) . . . . ?
C29B S2A S2B C32A 2(7) . . . . ?
C29A S2A S2B C32A 4(7) . . . . ?
C29B S2A S2B C32B 3(5) . . . . ?
C29A S2A S2B C32B 6(6) . . . . ?
C32A S2A S2B C32B 1(6) . . . . ?
C29A S2A S2B C29B 2.8(15) . . . . ?
C32A S2A S2B C29B -2(7) . . . . ?
C29B S2A S2B C29A -2.8(15) . . . . ?
C32A S2A S2B C29A -4(7) . . . . ?
C29B S2A S2B C31A 1.0(19) . . . . ?
C29A S2A S2B C31A 4(2) . . . . ?
C32A S2A S2B C31A -1(6) . . . . ?
C31A C32A S2B S2A -1(8) . . . . ?
C31B C32A S2B S2A -3(8) . . . . ?
C31A C32A S2B C32B -23(80) . . . . ?
C31B C32A S2B C32B -26(79) . . . . ?
S2A C32A S2B C32B -23(85) . . . . ?
C31A C32A S2B C29B 0.7(18) . . . . ?
C31B C32A S2B C29B -2(3) . . . . ?
S2A C32A S2B C29B 1(7) . . . . ?
C31A C32A S2B C29A 3(2) . . . . ?
C31B C32A S2B C29A 1(3) . . . . ?
S2A C32A S2B C29A 4(6) . . . . ?
C31B C32A S2B C31A -2.4(17) . . . . ?
S2A C32A S2B C31A 1(8) . . . . ?
C32A C32B S2B S2A -159(80) . . . . ?
C31B C32B S2B S2A -6(6) . . . . ?
C31A C32B S2B S2A -3(6) . . . . ?
C31B C32B S2B C32A 153(83) . . . . ?
C31A C32B S2B C32A 156(82) . . . . ?
C32A C32B S2B C29B -156(81) . . . . ?
C31B C32B S2B C29B -3(2) . . . . ?
C31A C32B S2B C29B -0.1(16) . . . . ?
C32A C32B S2B C29A -154(81) . . . . ?
C31B C32B S2B C29A -1(2) . . . . ?
C31A C32B S2B C29A 2.0(18) . . . . ?
C32A C32B S2B C31A -156(82) . . . . ?
C31B C32B S2B C31A -2.9(17) . . . . ?
C30B C29B S2B S2A -179(3) . . . . ?
C30A C29B S2B S2A -177(2) . . . . ?
Cl6B C29B S2B S2A -1(2) . . . . ?
C31A C29B S2B S2A 179(2) . . . . ?
Cl6A C29B S2B S2A -4(2) . . . . ?
C30B C29B S2B C32A 1(2) . . . . ?
C30A C29B S2B C32A 3.3(17) . . . . ?
S2A C29B S2B C32A -179(2) . . . . ?
Cl6B C29B S2B C32A 179.9(18) . . . . ?
C31A C29B S2B C32A -0.5(14) . . . . ?
Cl6A C29B S2B C32A 176.3(16) . . . . ?
C30B C29B S2B C32B 2(2) . . . . ?
C30A C29B S2B C32B 3.9(15) . . . . ?
S2A C29B S2B C32B -179(2) . . . . ?
Cl6B C29B S2B C32B -179.6(17) . . . . ?
C31A C29B S2B C32B 0.1(12) . . . . ?
Cl6A C29B S2B C32B 176.8(15) . . . . ?
C30B C29B S2B C29A -169(7) . . . . ?
C30A C29B S2B C29A -168(6) . . . . ?
S2A C29B S2B C29A 10(5) . . . . ?
Cl6B C29B S2B C29A 9(4) . . . . ?
C31A C29B S2B C29A -171(6) . . . . ?
Cl6A C29B S2B C29A 5(4) . . . . ?
C30B C29B S2B C31A 1.9(15) . . . . ?
C30A C29B S2B C31A 3.8(9) . . . . ?
S2A C29B S2B C31A -179(2) . . . . ?
Cl6B C29B S2B C31A -179.6(19) . . . . ?
Cl6A C29B S2B C31A 176.8(18) . . . . ?
Cl6B C29A Cl6A C29B 91(17) . . . . ?
C30B C29A Cl6A C29B -16(11) . . . . ?
S2A C29A Cl6A C29B 159(13) . . . . ?
C30A C29A Cl6A C29B -19(11) . . . . ?
S2B C29A Cl6A C29B 160(14) . . . . ?
C30B C29A Cl6B C29B -24(10) . . . . ?
Cl6A C29A Cl6B C29B -99(17) . . . . ?
S2A C29A Cl6B C29B 146(13) . . . . ?
C30A C29A Cl6B C29B -25(10) . . . . ?
S2B C29A Cl6B C29B 144(13) . . . . ?
C30B C29B Cl6B C29A 150(13) . . . . ?
C30A C29B Cl6B C29A 147(13) . . . . ?
S2A C29B Cl6B C29A -29(11) . . . . ?
S2B C29B Cl6B C29A -29(11) . . . . ?
C31A C29B Cl6B C29A 153(17) . . . . ?
Cl6A C29B Cl6B C29A 101(17) . . . . ?

_refine_diff_density_max         0.435
_refine_diff_density_min         -0.673
_refine_diff_density_rms         0.093

####################################################################### 
# 
# 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_TCA-LTAH
_database_code_depnum_ccdc_archive 'CCDC 2296507'
loop_
_audit_author_name
_audit_author_address
'Tejender Thakur'
;CSIR Central Drug Research Institute
India
;
_audit_update_record             
;
2023-09-21 deposited with the CCDC.	2023-11-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/2
_shelx_SHELXL_version_number     2019/2
_chemical_name_systematic        ?
_chemical_name_common            'Tioconazole-L-tartrate 1:1 salt hydrate'
_chemical_melting_point          ?
_chemical_formula_moiety         
'C16 H14 Cl3 N2 O S, C4 H5 O6, 3(H2 O), 0.42(O)'
_chemical_formula_sum            'C20 H25 Cl3 N2 O10.42 S'
_chemical_formula_weight         598.57

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'
Cl Cl 0.3639 0.7018 '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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_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, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   7.60280(10)
_cell_length_b                   9.94440(10)
_cell_length_c                   35.6016(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2691.67(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    54997
_cell_measurement_theta_min      2.4770
_cell_measurement_theta_max      76.6930

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.477
_exptl_crystal_F_000             1237
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    4.312
_shelx_estimated_absorpt_T_min   0.465
_shelx_estimated_absorpt_T_max   0.724
_exptl_absorpt_correction_T_min  0.42537
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.88a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.338
_oxdiff_exptl_absorpt_empirical_full_max 3.985
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_type            HyPix
_diffrn_detector_area_resol_mean 10.0000
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1068175000
_diffrn_orient_matrix_UB_12      0.0841283000
_diffrn_orient_matrix_UB_13      0.0282759000
_diffrn_orient_matrix_UB_21      -0.0260247000
_diffrn_orient_matrix_UB_22      0.1099391000
_diffrn_orient_matrix_UB_23      -0.0300082000
_diffrn_orient_matrix_UB_31      -0.1701809000
_diffrn_orient_matrix_UB_32      -0.0695602000
_diffrn_orient_matrix_UB_33      -0.0131427000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -19.00  22.00   0.50    0.05    --   14.00 100.00-175.98   82
  2  ω      2.00  43.00   0.50    0.05    --   30.00  88.00 -80.38   82
  3  ω    -20.00   7.00   0.50    0.05    --   14.00 103.00 -20.34   54
  4  ω      0.00  34.00   0.50    0.05    --   30.00  93.00 115.73   68
  5  ω     13.00  42.00   0.50    0.05    --   42.00  91.00  12.02   58
  6  ω     14.00  43.00   0.50    0.05    --   42.00  88.00  87.55   58
  7  ω     25.00 119.00   0.50    0.05    --   47.33  77.00 120.00  188
  8  ω     35.00 122.00   0.50    0.05    --   47.33  19.00 150.00  174
  9  ω     32.00 126.00   0.50    0.05    --   54.00  75.00  33.66  188
 10  ω     44.00 139.00   0.50    0.05    --   66.00  75.00 -25.96  190
 11  ω     44.00 139.00   0.50    0.05    --   66.00  76.00 -69.39  190
 12  ω     25.00 119.00   0.50    0.05    --   47.33  77.00-150.00  188
 13  ω     33.00 126.00   0.50    0.05    --   54.00  74.00-127.64  186
 14  ω     38.00 131.00   0.50    0.05    --   58.00  71.00 -99.18  186
 15  ω     44.00 139.00   0.50    0.05    --   66.00  76.00 -69.39  190
 16  ω    120.00 174.00   0.50    0.22    --  109.61 125.00 -30.00  108
 17  ω    107.00 178.00   0.50    0.22    --  109.61 101.00   4.00  142
 18  ω     38.00  63.00   0.50    0.22    --  109.61 -57.00  30.00   50
 19  ω     38.00  63.00   0.50    0.22    --  109.61 -57.00  60.00   50
 20  ω     38.00  63.00   0.50    0.22    --  109.61 -57.00 120.00   50
 21  ω     40.00 106.00   0.50    0.22    --  109.61-125.00 120.00  132
 22  ω     41.00 109.00   0.50    0.22    --  109.61-125.00 150.00  136
 23  ω     77.00 108.00   0.50    0.22    --  109.61-125.00 -30.00   62
 24  ω     81.00 106.00   0.50    0.22    --  109.61 -99.00 -30.00   50
 25  ω     40.00  68.00   0.50    0.22    --  109.61-125.00 -30.00   56
 26  ω     39.00 106.00   0.50    0.22    --  109.61-101.00 -99.00  134
 27  ω     71.00 105.00   0.50    0.22    --  109.61 -99.00-150.00   68
 28  ω     40.00  66.00   0.50    0.22    --  109.61 -99.00-150.00   52
 29  ω     39.00  74.00   0.50    0.22    --  109.61 -99.00 -30.00   70
 30  ω     48.00  89.00   0.50    0.22    --  109.61 -99.00 -60.00   82
 31  ω     39.00 106.00   0.50    0.22    --  109.61 -99.00 150.00  134
 32  ω     77.00 104.00   0.50    0.22    --  109.61 -99.00  30.00   54
 33  ω     44.00  73.00   0.50    0.22    --  109.61 -99.00  30.00   58
 34  ω      4.00  81.00   0.50    0.05    --   47.33-101.00 -99.00  154
 35  ω     34.00  93.00   0.50    0.05    --   47.33-125.00-180.00  118
 36  ω     34.00  93.00   0.50    0.05    --   47.33-125.00   0.00  118
 37  ω   -119.00 -25.00   0.50    0.05    --  -47.33 -77.00 120.00  188
 38  ω   -119.00 -25.00   0.50    0.05    --  -47.33 -77.00 -60.00  188
 39  ω   -119.00 -25.00   0.50    0.05    --  -47.33 -77.00 -90.00  188
 40  ω   -119.00 -25.00   0.50    0.05    --  -47.33 -77.00-180.00  188
 41  ω   -162.00 -85.00   0.50    0.22    --  -91.75-101.00 -99.00  154
 42  ω    -92.00 -59.00   0.50    0.22    --  -82.00 -77.00-110.52   66
 43  ω   -126.00 -31.00   0.50    0.05    --  -54.00 -77.00 -99.09  190
 44  ω   -156.00-127.00   0.50    0.22    --  -91.75 -77.00-162.74   58
 45  ω   -110.00 -69.00   0.50    0.22    --  -91.75 -77.00-162.74   82
 46  ω    -89.00 -63.00   0.50    0.22    --  -86.00 -77.00 -55.63   52
 47  ω   -110.00 -69.00   0.50    0.22    --  -91.75 -77.00 -30.00   82
 48  ω   -151.00 -69.00   0.50    0.22    --  -91.75 -77.00 -65.36  164
 49  ω   -162.00-136.00   0.50    0.22    --  -91.75 -77.00 -30.00   52
 50  ω   -114.00 -69.00   0.50    0.22    --  -91.75 -77.00  90.00   90
 51  ω   -139.00 -43.00   0.50    0.05    --  -66.00 -77.00 176.54  192
 52  ω   -147.00-121.00   0.50    0.22    --  -91.75 -77.00  90.00   52
 53  ω   -161.00 -94.00   0.50    0.22    --  -91.75 -77.00  30.00  134
 54  ω    -77.00 -51.00   0.50    0.05    --  -74.00 -76.00  69.91   52
 55  ω    -77.00 -51.00   0.50    0.05    --  -74.00 -76.00 -20.06   52
 56  ω   -161.00 -69.00   0.50    0.22    --  -91.75 -77.00-180.00  184
 57  ω   -139.00 -43.00   0.50    0.05    --  -66.00 -76.00-123.20  192
 58  ω   -143.00 -47.00   0.50    0.05    --  -70.00 -77.00   0.34  192
 59  ω   -144.00 -67.00   0.50    0.22    --  -90.00 -76.00  61.89  154
 60  ω    -77.00 -51.00   0.50    0.05    --  -74.00 -76.00 145.45   52
 61  ω    -88.00 -63.00   0.50    0.22    --  -86.00 -76.00 136.35   50
 62  ω   -154.00-104.00   0.50    0.22    --  -86.00 -76.00 136.35  100
 63  ω    -98.00 -69.00   0.50    0.22    --  -91.75 -76.00  -0.79   58
 64  ω    -94.00 -69.00   0.50    0.22    --  -91.75 -76.00  15.30   50
 65  ω   -154.00-110.00   0.50    0.22    --  -91.75 -76.00  15.30   88
 66  ω   -163.00-128.00   0.50    0.22    --  -91.75 -76.00  -0.79   70
 67  ω    -78.00 -52.00   0.50    0.05    --  -74.00 -74.00 -79.53   52
 68  ω    -86.00 -60.00   0.50    0.22    --  -82.00 -75.00-130.18   52
 69  ω    -85.00 -52.00   0.50    0.05    --  -74.00 -75.00-150.35   66
 70  ω   -143.00 -70.00   0.50    0.22    --  -91.75 -75.00-147.78  146
 71  ω    -82.00 -56.00   0.50    0.05    --  -78.00 -74.00 106.21   52
 72  ω    -79.00 -53.00   0.50    0.05    --  -74.00 -74.00 130.10   52
 73  ω   -146.00 -70.00   0.50    0.22    --  -91.75 -74.00 160.43  152
 74  ω   -163.00-113.00   0.50    0.22    --  -91.75 -74.00 128.67  100
 75  ω   -101.00 -71.00   0.50    0.22    --  -91.75 -74.00 128.67   60
 76  ω   -100.00 -64.00   0.50    0.22    --  -86.00 -74.00  49.13   72
 77  ω   -148.00-108.00   0.50    0.22    --  -86.00 -74.00  49.13   80
 78  ω   -135.00 -40.00   0.50    0.05    --  -62.00 -74.00  32.89  190
 79  ω    -86.00 -60.00   0.50    0.22    --  -82.00 -74.00 -38.52   52
 80  ω    -88.00 -62.00   0.50    0.22    --  -82.00 -73.00 -94.99   52
 81  ω   -154.00-116.00   0.50    0.22    --  -82.00 -73.00 -94.99   76
 82  ω   -151.00-126.00   0.50    0.22    --  -91.75 -71.00-138.10   50
 83  ω   -161.00 -75.00   0.50    0.22    --  -91.75 -72.00 -82.38  172
 84  ω   -101.00 -71.00   0.50    0.22    --  -91.75 -71.00-138.10   60
 85  ω    -83.00 -54.00   0.50    0.05    --  -74.00 -71.00  15.93   58
 86  ω   -107.00 -71.00   0.50    0.22    --  -91.75 -71.00 102.54   72
 87  ω   -163.00-112.00   0.50    0.22    --  -91.75 -71.00 102.54  102
 88  ω   -139.00 -46.00   0.50    0.05    --  -66.00 -71.00  83.90  186
 89  ω   -101.00 -74.00   0.50    0.22    --  -91.75 -70.00-111.95   54
 90  ω   -163.00-111.00   0.50    0.22    --  -91.75 -70.00-111.95  104
 91  ω   -154.00 -89.00   0.50    0.22    --  -91.75 -57.00 -30.00  130
 92  ω    -41.00  26.00   0.50    0.05    --  -47.33  38.00-150.00  134
 93  ω    -81.00  18.00   0.50    0.05    --  -47.33 101.00   4.00  198
 94  ω    -84.00 -44.00   0.50    0.22    --  -91.75 125.00 -60.00   80
 95  ω    -78.00 -34.00   0.50    0.22    --  -91.75 101.00   4.00   88
;
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_number            93425
_diffrn_reflns_av_unetI/netI     0.0270
_diffrn_reflns_av_R_equivalents  0.1116
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -44
_diffrn_reflns_limit_l_max       43
_diffrn_reflns_theta_min         2.482
_diffrn_reflns_theta_max         77.786
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             5579
_reflns_number_gt                5273
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.714
_reflns_Friedel_fraction_max     0.949
_reflns_Friedel_fraction_full    1.000

_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 1.171.42.88a (Rigaku OD, 2023)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.88a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.88a (Rigaku OD, 2023)'
_computing_structure_solution    'SHELXL-2018/2 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_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)+(0.0357P)²+3.1046P] 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_abs_structure_details 
;
 Flack x determined using 1917 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.046(7)
_chemical_absolute_configuration .
_refine_ls_number_reflns         5579
_refine_ls_number_parameters     366
_refine_ls_number_restraints     8
_refine_ls_R_factor_all          0.0641
_refine_ls_R_factor_gt           0.0618
_refine_ls_wR_factor_ref         0.1312
_refine_ls_wR_factor_gt          0.1301
_refine_ls_goodness_of_fit_ref   1.146
_refine_ls_restrained_S_all      1.151
_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
C20 C 1.1984(6) 0.4603(5) 0.08931(13) 0.0346(9) Uani 1 1 d . . . . .
C14 C 0.4032(6) 1.0973(5) 0.19242(13) 0.0419(11) Uani 1 1 d . . . . .
C1 C 0.1706(7) 0.7868(5) 0.16078(14) 0.0430(11) Uani 1 1 d . . . . .
C8 C 0.1884(7) 0.9107(6) 0.09904(14) 0.0491(12) Uani 1 1 d . . . . .
H8A H 0.233817 0.992248 0.087650 0.059 Uiso 1 1 calc R U . . .
H8B H 0.250235 0.835255 0.087924 0.059 Uiso 1 1 calc R U . . .
C2 C 0.2827(7) 0.6787(6) 0.16548(14) 0.0459(11) Uani 1 1 d . . . . .
C15 C 0.4860(8) 1.1972(6) 0.16962(15) 0.0530(12) Uani 1 1 d . . . . .
H15 H 0.424435 1.251981 0.153027 0.064 Uiso 1 1 calc R U . . .
C12 C 0.2085(7) 1.0683(6) 0.19186(15) 0.0507(13) Uani 1 1 d . . . . .
H12A H 0.183360 0.995403 0.209146 0.061 Uiso 1 1 calc R U . . .
H12B H 0.145180 1.147206 0.200422 0.061 Uiso 1 1 calc R U . . .
C4 C 0.0628(8) 0.5543(5) 0.19738(14) 0.0488(13) Uani 1 1 d . . . . .
C13 C 0.5235(8) 1.0335(6) 0.21367(15) 0.0507(12) Uani 1 1 d . . . . .
C11 C -0.1247(9) 0.9984(6) 0.0945(2) 0.0694(19) Uani 1 1 d . . . . .
H11 H -0.106810 1.084430 0.103981 0.083 Uiso 1 1 calc R U . . .
C5 C -0.0541(8) 0.6588(7) 0.19341(16) 0.0564(14) Uani 1 1 d . . . . .
H5 H -0.167708 0.652244 0.202913 0.068 Uiso 1 1 calc R U . . .
C6 C 0.0005(8) 0.7736(6) 0.17504(15) 0.0526(12) Uani 1 1 d . . . . .
H6 H -0.078390 0.844315 0.172081 0.063 Uiso 1 1 calc R U . . .
C16 C 0.6594(8) 1.2044(7) 0.17437(18) 0.0641(17) Uani 1 1 d . . . . .
H16 H 0.731898 1.263766 0.161392 0.077 Uiso 1 1 calc R U . . .
C10 C -0.2773(9) 0.9461(7) 0.0823(2) 0.077(2) Uani 1 1 d . . . . .
H10 H -0.385277 0.990021 0.081650 0.092 Uiso 1 1 calc R U . . .
C17 C 0.7184(6) 0.3559(5) 0.06959(14) 0.0393(10) Uani 1 1 d . . . . .
C19 C 1.0103(6) 0.4166(5) 0.09878(12) 0.0354(9) Uani 1 1 d . . . . .
H19 H 0.952459 0.490087 0.112347 0.043 Uiso 1 1 calc R U . . .
C9 C -0.0760(8) 0.7911(5) 0.07583(16) 0.0495(12) Uani 1 1 d . . . . .
H9 H -0.020205 0.710402 0.070106 0.059 Uiso 1 1 calc R U . . .
C7 C 0.2272(6) 0.9140(5) 0.14063(14) 0.0439(11) Uani 1 1 d . . . . .
H7 H 0.354714 0.923033 0.143690 0.053 Uiso 1 1 calc R U . . .
C18 C 0.9103(6) 0.3919(5) 0.06235(13) 0.0387(10) Uani 1 1 d . . . . .
H18 H 0.913719 0.474572 0.047370 0.046 Uiso 1 1 calc R U . . .
C3 C 0.2312(8) 0.5617(5) 0.18337(14) 0.0483(12) Uani 1 1 d . . . . .
H3 H 0.308521 0.489813 0.185869 0.058 Uiso 1 1 calc R U . . .
Cl1 Cl 0.4969(2) 0.68446(17) 0.14846(5) 0.0668(4) Uani 1 1 d . . . . .
Cl2 Cl -0.0009(3) 0.40882(15) 0.22096(4) 0.0696(4) Uani 1 1 d . . . . .
Cl3 Cl 0.4873(3) 0.9027(2) 0.24417(5) 0.0902(6) Uani 1 1 d . . . . .
N1 N 0.0004(6) 0.8990(4) 0.09011(11) 0.0465(9) Uani 1 1 d . . . . .
N2 N -0.2459(7) 0.8174(5) 0.07104(16) 0.0594(12) Uani 1 1 d . . . . .
O7 O 1.3195(4) 0.3847(4) 0.10024(11) 0.0489(9) Uani 1 1 d . . . . .
O5 O 1.0080(5) 0.3008(4) 0.12182(10) 0.0491(8) Uani 1 1 d . . . . .
H5O H 1.105372 0.265311 0.121571 0.074 Uiso 1 1 calc R U . . .
O6 O 1.2150(5) 0.5680(4) 0.07168(11) 0.0516(9) Uani 1 1 d . . . . .
O2 O 0.6381(4) 0.4477(4) 0.08881(13) 0.0593(11) Uani 1 1 d . . . . .
H2O H 0.533041 0.429732 0.090029 0.089 Uiso 1 1 calc R U . . .
O8 O 0.4795(5) 0.6935(4) 0.03486(13) 0.0587(10) Uani 1 1 d D . . . .
O4 O 0.9967(5) 0.2899(4) 0.04221(11) 0.0606(10) Uani 1 1 d . . . . .
H4O H 0.965139 0.291926 0.020192 0.091 Uiso 1 1 calc R U . . .
O3 O 0.6521(5) 0.2539(4) 0.05771(14) 0.0664(12) Uani 1 1 d . . . . .
O9 O 0.2690(7) 0.8971(5) 0.00765(14) 0.0682(11) Uani 1 1 d D . . . .
O10 O 0.3269(6) 0.1656(5) 0.03138(14) 0.0721(13) Uani 1 1 d D . . . .
O1 O 0.1477(5) 1.0324(4) 0.15522(11) 0.0478(8) Uani 1 1 d . . . . .
S1 S 0.73340(19) 1.0921(2) 0.20705(5) 0.0653(4) Uani 1 1 d . . . . .
O11 O 0.830(6) 0.039(3) 0.0062(7) 0.27(2) Uani 0.42(2) 1 d . . . . .
H9B H 0.26(2) 0.976(7) 0.020(4) 0.20(6) Uiso 1 1 d D . . . .
H10B H 0.246(8) 0.223(7) 0.039(2) 0.12(3) Uiso 1 1 d D . . . .
H8D H 0.414(9) 0.756(6) 0.0237(19) 0.08(2) Uiso 1 1 d D . . . .
H2N H -0.329(7) 0.768(5) 0.0561(15) 0.042(14) Uiso 1 1 d . . . . .
H8C H 0.413(11) 0.657(9) 0.052(2) 0.13(4) Uiso 1 1 d D . . . .
H9A H 0.153(5) 0.891(12) 0.002(3) 0.14(4) Uiso 1 1 d D . . . .
H10A H 0.408(9) 0.201(9) 0.048(2) 0.13(4) Uiso 1 1 d 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
C20 O6 1.247(6) . ?
C20 O7 1.251(6) . ?
C20 C19 1.533(6) . ?
C14 C13 1.346(7) . ?
C14 C15 1.428(7) . ?
C14 C12 1.508(7) . ?
C1 C2 1.382(7) . ?
C1 C6 1.395(8) . ?
C1 C7 1.517(7) . ?
C8 N1 1.469(7) . ?
C8 C7 1.510(7) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C2 C3 1.382(8) . ?
C2 Cl1 1.739(5) . ?
C15 C16 1.332(9) . ?
C15 H15 0.9300 . ?
C12 O1 1.429(6) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C4 C5 1.375(8) . ?
C4 C3 1.376(8) . ?
C4 Cl2 1.741(6) . ?
C13 S1 1.715(6) . ?
C13 Cl3 1.717(6) . ?
C11 C10 1.344(9) . ?
C11 N1 1.380(8) . ?
C11 H11 0.9300 . ?
C5 C6 1.380(8) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C16 S1 1.708(7) . ?
C16 H16 0.9300 . ?
C10 N2 1.363(8) . ?
C10 H10 0.9300 . ?
C17 O3 1.209(6) . ?
C17 O2 1.294(6) . ?
C17 C18 1.524(6) . ?
C19 O5 1.414(5) . ?
C19 C18 1.523(6) . ?
C19 H19 0.9800 . ?
C9 N1 1.322(7) . ?
C9 N2 1.329(8) . ?
C9 H9 0.9300 . ?
C7 O1 1.421(6) . ?
C7 H7 0.9800 . ?
C18 O4 1.406(6) . ?
C18 H18 0.9800 . ?
C3 H3 0.9300 . ?
N2 H2N 0.96(6) . ?
O5 H5O 0.8200 . ?
O2 H2O 0.8200 . ?
O8 H8D 0.89(3) . ?
O8 H8C 0.89(3) . ?
O4 H4O 0.8200 . ?
O9 H9B 0.90(3) . ?
O9 H9A 0.90(3) . ?
O10 H10B 0.88(3) . ?
O10 H10A 0.93(2) . ?

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
O6 C20 O7 126.8(4) . . ?
O6 C20 C19 116.7(4) . . ?
O7 C20 C19 116.6(4) . . ?
C13 C14 C15 110.4(5) . . ?
C13 C14 C12 125.7(5) . . ?
C15 C14 C12 123.9(5) . . ?
C2 C1 C6 117.0(5) . . ?
C2 C1 C7 122.1(5) . . ?
C6 C1 C7 120.9(5) . . ?
N1 C8 C7 113.8(4) . . ?
N1 C8 H8A 108.8 . . ?
C7 C8 H8A 108.8 . . ?
N1 C8 H8B 108.8 . . ?
C7 C8 H8B 108.8 . . ?
H8A C8 H8B 107.7 . . ?
C1 C2 C3 122.4(5) . . ?
C1 C2 Cl1 120.7(4) . . ?
C3 C2 Cl1 117.0(4) . . ?
C16 C15 C14 113.7(5) . . ?
C16 C15 H15 123.2 . . ?
C14 C15 H15 123.2 . . ?
O1 C12 C14 112.2(4) . . ?
O1 C12 H12A 109.2 . . ?
C14 C12 H12A 109.2 . . ?
O1 C12 H12B 109.2 . . ?
C14 C12 H12B 109.2 . . ?
H12A C12 H12B 107.9 . . ?
C5 C4 C3 121.6(5) . . ?
C5 C4 Cl2 119.9(5) . . ?
C3 C4 Cl2 118.5(4) . . ?
C14 C13 S1 113.3(4) . . ?
C14 C13 Cl3 127.1(5) . . ?
S1 C13 Cl3 119.6(3) . . ?
C10 C11 N1 106.4(5) . . ?
C10 C11 H11 126.8 . . ?
N1 C11 H11 126.8 . . ?
C4 C5 C6 118.7(5) . . ?
C4 C5 H5 120.7 . . ?
C6 C5 H5 120.7 . . ?
C5 C6 C1 121.9(5) . . ?
C5 C6 H6 119.0 . . ?
C1 C6 H6 119.0 . . ?
C15 C16 S1 112.1(5) . . ?
C15 C16 H16 123.9 . . ?
S1 C16 H16 123.9 . . ?
C11 C10 N2 107.9(6) . . ?
C11 C10 H10 126.1 . . ?
N2 C10 H10 126.1 . . ?
O3 C17 O2 125.5(4) . . ?
O3 C17 C18 122.5(5) . . ?
O2 C17 C18 112.0(4) . . ?
O5 C19 C18 110.9(4) . . ?
O5 C19 C20 111.7(4) . . ?
C18 C19 C20 108.9(3) . . ?
O5 C19 H19 108.4 . . ?
C18 C19 H19 108.4 . . ?
C20 C19 H19 108.4 . . ?
N1 C9 N2 108.4(5) . . ?
N1 C9 H9 125.8 . . ?
N2 C9 H9 125.8 . . ?
O1 C7 C8 107.1(4) . . ?
O1 C7 C1 113.4(4) . . ?
C8 C7 C1 113.0(4) . . ?
O1 C7 H7 107.7 . . ?
C8 C7 H7 107.7 . . ?
C1 C7 H7 107.7 . . ?
O4 C18 C19 108.5(4) . . ?
O4 C18 C17 111.4(4) . . ?
C19 C18 C17 111.8(4) . . ?
O4 C18 H18 108.3 . . ?
C19 C18 H18 108.3 . . ?
C17 C18 H18 108.3 . . ?
C4 C3 C2 118.4(5) . . ?
C4 C3 H3 120.8 . . ?
C2 C3 H3 120.8 . . ?
C9 N1 C11 108.8(5) . . ?
C9 N1 C8 125.1(5) . . ?
C11 N1 C8 126.1(5) . . ?
C9 N2 C10 108.5(5) . . ?
C9 N2 H2N 128(3) . . ?
C10 N2 H2N 122(3) . . ?
C19 O5 H5O 109.5 . . ?
C17 O2 H2O 109.5 . . ?
H8D O8 H8C 107(8) . . ?
C18 O4 H4O 109.5 . . ?
H9B O9 H9A 95(10) . . ?
H10B O10 H10A 92(5) . . ?
C7 O1 C12 113.8(4) . . ?
C16 S1 C13 90.5(3) . . ?

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
C6 C1 C2 C3 0.1(8) . . . . ?
C7 C1 C2 C3 -179.1(5) . . . . ?
C6 C1 C2 Cl1 179.6(4) . . . . ?
C7 C1 C2 Cl1 0.4(7) . . . . ?
C13 C14 C15 C16 0.1(7) . . . . ?
C12 C14 C15 C16 -179.2(6) . . . . ?
C13 C14 C12 O1 -121.6(6) . . . . ?
C15 C14 C12 O1 57.5(7) . . . . ?
C15 C14 C13 S1 0.5(6) . . . . ?
C12 C14 C13 S1 179.8(4) . . . . ?
C15 C14 C13 Cl3 -177.7(4) . . . . ?
C12 C14 C13 Cl3 1.6(9) . . . . ?
C3 C4 C5 C6 -0.3(8) . . . . ?
Cl2 C4 C5 C6 179.1(4) . . . . ?
C4 C5 C6 C1 -0.6(9) . . . . ?
C2 C1 C6 C5 0.7(8) . . . . ?
C7 C1 C6 C5 179.9(5) . . . . ?
C14 C15 C16 S1 -0.6(8) . . . . ?
N1 C11 C10 N2 0.5(9) . . . . ?
O6 C20 C19 O5 -174.3(4) . . . . ?
O7 C20 C19 O5 5.4(6) . . . . ?
O6 C20 C19 C18 62.9(5) . . . . ?
O7 C20 C19 C18 -117.5(5) . . . . ?
N1 C8 C7 O1 -63.7(6) . . . . ?
N1 C8 C7 C1 61.9(6) . . . . ?
C2 C1 C7 O1 -146.9(5) . . . . ?
C6 C1 C7 O1 34.0(6) . . . . ?
C2 C1 C7 C8 91.1(6) . . . . ?
C6 C1 C7 C8 -88.1(6) . . . . ?
O5 C19 C18 O4 -63.2(5) . . . . ?
C20 C19 C18 O4 60.1(5) . . . . ?
O5 C19 C18 C17 60.0(5) . . . . ?
C20 C19 C18 C17 -176.7(4) . . . . ?
O3 C17 C18 O4 -2.7(7) . . . . ?
O2 C17 C18 O4 178.6(4) . . . . ?
O3 C17 C18 C19 -124.3(6) . . . . ?
O2 C17 C18 C19 57.1(6) . . . . ?
C5 C4 C3 C2 1.0(8) . . . . ?
Cl2 C4 C3 C2 -178.4(4) . . . . ?
C1 C2 C3 C4 -0.9(8) . . . . ?
Cl1 C2 C3 C4 179.6(4) . . . . ?
N2 C9 N1 C11 -0.3(7) . . . . ?
N2 C9 N1 C8 -179.2(5) . . . . ?
C10 C11 N1 C9 -0.1(8) . . . . ?
C10 C11 N1 C8 178.8(6) . . . . ?
C7 C8 N1 C9 -109.4(6) . . . . ?
C7 C8 N1 C11 71.9(8) . . . . ?
N1 C9 N2 C10 0.6(7) . . . . ?
C11 C10 N2 C9 -0.7(9) . . . . ?
C8 C7 O1 C12 -165.0(4) . . . . ?
C1 C7 O1 C12 69.7(5) . . . . ?
C14 C12 O1 C7 61.4(6) . . . . ?
C15 C16 S1 C13 0.8(6) . . . . ?
C14 C13 S1 C16 -0.7(5) . . . . ?
Cl3 C13 S1 C16 177.6(4) . . . . ?

_refine_diff_density_max         0.327
_refine_diff_density_min         -0.277
_refine_diff_density_rms         0.056

####################################################################### 
# 
# 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_TCZ-SULH2
_database_code_depnum_ccdc_archive 'CCDC 2296669'
loop_
_audit_author_name
_audit_author_address
'Tejender Thakur'
;CSIR Central Drug Research Institute
India
;
_audit_update_record             
;
2023-09-22 deposited with the CCDC.	2023-11-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/2
_shelx_SHELXL_version_number     2019/2

# start Validation Reply Form
_vrf_PLAT340_TCZ-SULH2           
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.01162 Ang.  
RESPONSE: Poor crystal quality and disordered atoms
;
_vrf_PLAT915_TCZ-SULH2           
;
PROBLEM: No Flack x Check Done: Low Friedel Pair Coverage         35 %     
RESPONSE: Compound is a recemic mixture solved in non-centrosymmetric space group
;
# end Validation Reply Form

_chemical_name_systematic        ?
_chemical_name_common            'Tioconzaole sulfate (2:1) salt heptahydrate'
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C16 H14 Cl3 N2 O S), O4 S, 7(H2 O)'
_chemical_formula_sum            'C32 H42 Cl6 N4 O13 S3'
_chemical_formula_weight         999.57

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'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           1
_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'

_cell_length_a                   10.5568(3)
_cell_length_b                   10.9083(3)
_cell_length_c                   20.8988(4)
_cell_angle_alpha                86.078(2)
_cell_angle_beta                 77.368(2)
_cell_angle_gamma                66.240(3)
_cell_volume                     2148.82(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    18112
_cell_measurement_theta_min      2.1740
_cell_measurement_theta_max      79.3000

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.545
_exptl_crystal_F_000             1032
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.270
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    5.575
_shelx_estimated_absorpt_T_min   0.314
_shelx_estimated_absorpt_T_max   0.897
_exptl_absorpt_correction_T_min  0.49291
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.88a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.497
_oxdiff_exptl_absorpt_empirical_full_max 2.167
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_type            HyPix
_diffrn_detector_area_resol_mean 10.0000
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0804003000
_diffrn_orient_matrix_UB_12      0.0778925000
_diffrn_orient_matrix_UB_13      0.0189489000
_diffrn_orient_matrix_UB_21      0.1018477000
_diffrn_orient_matrix_UB_22      -0.0354203000
_diffrn_orient_matrix_UB_23      -0.0675321000
_diffrn_orient_matrix_UB_31      -0.0987452000
_diffrn_orient_matrix_UB_32      0.1284549000
_diffrn_orient_matrix_UB_33      -0.0281073000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -24.00  24.00   0.50    0.09    --  -47.08  19.00  60.00   96
  2  ω    -62.00  24.00   0.50    0.09    --  -47.08  57.00  60.00  172
  3  ω    -17.00  25.00   0.50    0.09    --  -47.08  38.00 -60.00   84
  4  ω    -25.00  25.00   0.50    0.09    --  -47.08  38.00-180.00  100
  5  ω    130.00 177.00   0.50    0.37    --  113.25  77.00 -30.00   94
  6  ω    140.00 177.00   0.50    0.37    --  113.25  45.00   0.00   74
  7  ω     96.00 121.00   0.50    0.37    --  113.25  77.00 -30.00   50
  8  ω    102.00 177.00   0.50    0.37    --  113.25  61.00 -60.00  150
  9  ω     98.00 152.00   0.50    0.37    --  113.25  61.00-120.00  108
 10  ω    102.00 138.00   0.50    0.37    --  113.25  45.00-120.00   72
 11  ω    103.00 169.00   0.50    0.37    --  113.25  30.00 -60.00  132
 12  ω    101.00 155.00   0.50    0.37    --  113.25  30.00  30.00  108
 13  ω    101.00 178.00   0.50    0.37    --  113.25  30.00  60.00  154
 14  ω    142.00 167.00   0.50    0.37    --  113.25  30.00  90.00   50
 15  ω    105.00 143.00   0.50    0.37    --  113.25  30.00 120.00   76
 16  ω    106.00 178.00   0.50    0.37    --  113.25  30.00 150.00  144
 17  ω    102.00 140.00   0.50    0.37    --  113.25  30.00  90.00   76
 18  ω    149.00 176.00   0.50    0.37    --  113.25  94.00 -19.00   54
 19  ω     43.00  69.00   0.50    0.37    --  113.25 -61.00 120.00   52
 20  ω     67.00  92.00   0.50    0.37    --  113.25 -77.00  90.00   50
 21  ω     43.00  70.00   0.50    0.37    --  113.25 -61.00  90.00   54
 22  ω     42.00  73.00   0.50    0.37    --  113.25 -61.00  60.00   62
 23  ω     47.00  73.00   0.50    0.37    --  113.25 -61.00 -60.00   52
 24  ω     42.00  68.00   0.50    0.37    --  113.25 -61.00-120.00   52
 25  ω     59.00  95.00   0.50    0.37    --  113.25 -94.00-129.00   72
 26  ω     78.00 109.00   0.50    0.37    --  113.25-114.00-150.00   62
 27  ω     45.00  71.00   0.50    0.37    --  113.25-114.00-150.00   52
 28  ω     75.00 106.00   0.50    0.37    --  113.25 -99.00 -90.50   62
 29  ω     79.00 104.00   0.50    0.37    --  113.25 -95.00 -30.00   50
 30  ω     54.00  93.00   0.50    0.37    --  113.25 -95.00 -90.00   78
 31  ω     43.00  93.00   0.50    0.37    --  113.25 -95.00  60.00  100
 32  ω     49.00 107.00   0.50    0.37    --  113.25-104.00 123.35  116
 33  ω     53.00  94.00   0.50    0.37    --  113.25 -95.00 150.00   82
 34  ω     73.00 123.00   0.50    0.37    --  113.25-140.00 118.49  100
 35  ω     57.00  96.00   0.50    0.37    --  113.25 -95.00   0.00   78
 36  ω     46.00 103.00   0.50    0.37    --  113.25 -95.00  30.00  114
 37  ω     46.00  72.00   0.50    0.37    --  113.25 -95.00 -30.00   52
 38  ω     44.00 104.00   0.50    0.37    --  113.25 -95.00 -60.00  120
 39  ω     59.00 106.00   0.50    0.37    --  113.25 -95.00-150.00   94
 40  ω     53.00 100.00   0.50    0.37    --  113.25 -95.00-180.00   94
 41  ω     35.00  89.00   0.50    0.09    --   47.08-125.00-120.00  108
 42  ω     40.00  78.00   0.50    0.09    --   47.08 -94.00-129.00   76
 43  ω    -12.00  31.00   0.50    0.09    --   47.08 -94.00-129.00   86
 44  ω    -45.00 -18.00   0.50    0.09    --  -47.08  94.00 -19.00   54
 45  ω    -13.00  12.00   0.50    0.09    --  -47.08  94.00 -19.00   50
 46  ω    -49.00 -21.00   0.50    0.37    --  -91.75  45.00  60.00   56
 47  ω    -74.00 -49.00   0.50    0.37    --  -91.75  94.00 -19.00   50
 48  ω    -49.00 -21.00   0.50    0.37    --  -91.75  45.00   0.00   56
 49  ω   -115.00 -34.00   0.50    0.09    --  -47.08 -57.00 -90.00  162
 50  ω   -163.00-107.00   0.50    0.37    --  -91.75 -95.00 -30.00  112
 51  ω   -123.00 -91.00   0.50    0.37    --  -91.75 -94.00-129.00   64
;
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_number            28515
_diffrn_reflns_av_unetI/netI     0.0610
_diffrn_reflns_av_R_equivalents  0.0649
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         2.167
_diffrn_reflns_theta_max         80.287
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.962
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.962
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.657
_diffrn_reflns_point_group_measured_fraction_full 0.696
_reflns_number_total             12321
_reflns_number_gt                10349
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.365
_reflns_Friedel_fraction_max     0.351
_reflns_Friedel_fraction_full    0.397

_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 1.171.42.88a (Rigaku OD, 2023)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.88a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.88a (Rigaku OD, 2023)'
_computing_structure_solution    'SHELXL-2018/2 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_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)+(0.1495P)²+0.2603P] 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_abs_structure_details 
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   0.300(18)
_chemical_absolute_configuration .
_refine_ls_number_reflns         12321
_refine_ls_number_parameters     1176
_refine_ls_number_restraints     55
_refine_ls_R_factor_all          0.0773
_refine_ls_R_factor_gt           0.0677
_refine_ls_wR_factor_ref         0.2060
_refine_ls_wR_factor_gt          0.1937
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_restrained_S_all      1.101
_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
C1 C 1.3325(7) 1.0401(7) 0.1588(3) 0.0251(13) Uani 1 1 d . . . . .
C2 C 1.2965(8) 1.1122(8) 0.1036(3) 0.0297(15) Uani 1 1 d . . . . .
C3 C 1.3927(9) 1.1469(8) 0.0572(3) 0.0337(16) Uani 1 1 d . . . . .
H3 H 1.366188 1.195605 0.019411 0.040 Uiso 1 1 calc R U . . .
C4 C 1.5281(8) 1.1077(8) 0.0681(3) 0.0330(17) Uani 1 1 d . . . . .
C5 C 1.5676(9) 1.0392(9) 0.1227(4) 0.0377(18) Uani 1 1 d . . . . .
H5 H 1.660298 1.015544 0.129890 0.045 Uiso 1 1 calc R U . . .
C6 C 1.4691(8) 1.0052(8) 0.1672(4) 0.0323(16) Uani 1 1 d . . . . .
H6 H 1.496417 0.956296 0.204810 0.039 Uiso 1 1 calc R U . . .
C7 C 1.2285(7) 1.0028(7) 0.2095(3) 0.0237(13) Uani 1 1 d . . . . .
H7 H 1.136209 1.033837 0.195270 0.028 Uiso 1 1 calc R U . . .
C8 C 1.2059(7) 1.0688(7) 0.2750(3) 0.0253(13) Uani 1 1 d . . . . .
H8A H 1.294078 1.028736 0.292061 0.030 Uiso 1 1 calc R U . . .
H8B H 1.183574 1.165551 0.268910 0.030 Uiso 1 1 calc R U . . .
C9 C 1.1043(7) 0.9699(7) 0.3732(3) 0.0227(12) Uani 1 1 d . . . . .
H9 H 1.190566 0.916039 0.386103 0.027 Uiso 1 1 calc R U . . .
C10 C 0.8779(7) 1.0645(8) 0.3704(3) 0.0283(14) Uani 1 1 d . . . . .
H10 H 0.778658 1.087963 0.381259 0.034 Uiso 1 1 calc R U . . .
C11 C 0.9494(7) 1.1121(7) 0.3195(3) 0.0245(13) Uani 1 1 d . . . . .
H11 H 0.909498 1.174831 0.288160 0.029 Uiso 1 1 calc R U . . .
C12 C 1.2348(8) 0.7923(7) 0.1793(3) 0.0278(14) Uani 1 1 d . . . . .
H12A H 1.299255 0.696264 0.175576 0.033 Uiso 1 1 calc R U . . .
H12B H 1.239603 0.829458 0.134736 0.033 Uiso 1 1 calc R U . . .
C13 C 0.9721(8) 0.8637(7) 0.1793(3) 0.0290(14) Uani 1 1 d . . . . .
C14 C 1.0857(8) 0.8054(7) 0.2076(3) 0.0271(14) Uani 1 1 d . . . . .
C15 C 1.0446(8) 0.7588(8) 0.2714(4) 0.0308(15) Uani 1 1 d . . . . .
H15 H 1.109777 0.714682 0.298884 0.037 Uiso 1 1 calc R U . . .
C16 C 0.9070(8) 0.7825(8) 0.2891(3) 0.0304(14) Uani 1 1 d . . . . .
H16 H 0.863997 0.757642 0.329814 0.037 Uiso 1 1 calc R U . . .
C17 C 0.8486(7) 0.5228(7) 0.1582(3) 0.0254(14) Uani 1 1 d . . . . .
C18 C 0.8118(8) 0.6086(7) 0.1075(3) 0.0272(14) Uani 1 1 d . . . . .
C19 C 0.9133(9) 0.6387(8) 0.0615(3) 0.0334(16) Uani 1 1 d . . . . .
H19 H 0.886699 0.698426 0.026890 0.040 Uiso 1 1 calc R U . . .
C20 C 1.0525(8) 0.5799(8) 0.0677(3) 0.0293(15) Uani 1 1 d . . . . .
C21 C 1.0929(9) 0.4952(10) 0.1187(4) 0.043(2) Uani 1 1 d . . . . .
H21 H 1.188853 0.457129 0.122934 0.052 Uiso 1 1 calc R U . . .
C22 C 0.9910(9) 0.4673(10) 0.1631(4) 0.0396(19) Uani 1 1 d . . . . .
H22 H 1.018110 0.408744 0.198057 0.047 Uiso 1 1 calc R U . . .
C23 C 0.7412(7) 0.4900(7) 0.2088(3) 0.0234(13) Uani 1 1 d . . . . .
H23 H 0.651538 0.517686 0.192403 0.028 Uiso 1 1 calc R U . . .
C24 C 0.7109(7) 0.5666(7) 0.2729(3) 0.0245(13) Uani 1 1 d . . . . .
H24A H 0.796077 0.531106 0.292328 0.029 Uiso 1 1 calc R U . . .
H24B H 0.688471 0.662555 0.263763 0.029 Uiso 1 1 calc R U . . .
C25 C 0.6019(7) 0.4756(7) 0.3714(3) 0.0230(12) Uani 1 1 d . . . . .
H25 H 0.686567 0.423568 0.386076 0.028 Uiso 1 1 calc R U . . .
C26 C 0.3770(8) 0.5676(8) 0.3644(4) 0.0298(14) Uani 1 1 d . . . . .
H26 H 0.277725 0.591283 0.373670 0.036 Uiso 1 1 calc R U . . .
C27 C 0.4525(7) 0.6106(7) 0.3132(3) 0.0251(13) Uani 1 1 d . . . . .
H27 H 0.416015 0.669111 0.279796 0.030 Uiso 1 1 calc R U . . .
C28 C 0.7452(8) 0.2766(8) 0.1855(4) 0.0287(14) Uani 1 1 d . . . . .
H28A H 0.807974 0.180241 0.184816 0.034 Uiso 1 1 calc R U . . .
H28B H 0.752287 0.307662 0.139773 0.034 Uiso 1 1 calc R U . . .
C29 C 0.4797(8) 0.3641(7) 0.1877(3) 0.0277(14) Uani 1 1 d . . . . .
C30 C 0.5942(8) 0.2952(7) 0.2147(3) 0.0267(14) Uani 1 1 d . . . . .
C31 C 0.5529(8) 0.2420(8) 0.2765(3) 0.0313(15) Uani 1 1 d . . . . .
H31 H 0.617802 0.189636 0.302703 0.038 Uiso 1 1 calc R U . . .
C32 C 0.4114(9) 0.2740(8) 0.2937(3) 0.0329(16) Uani 1 1 d . . . . .
H32 H 0.366707 0.246866 0.333329 0.039 Uiso 1 1 calc R U . . .
C33 C -0.3406(8) -0.0382(7) 0.8389(3) 0.0260(14) Uani 1 1 d . . . . .
C34 C -0.3058(8) -0.1080(8) 0.8942(3) 0.0311(15) Uani 1 1 d . . . . .
C35 C -0.4004(9) -0.1449(9) 0.9403(3) 0.0369(17) Uani 1 1 d . . . . .
H35 H -0.371963 -0.194995 0.977391 0.044 Uiso 1 1 calc R U . . .
C36 C -0.5354(9) -0.1071(9) 0.9309(4) 0.0357(17) Uani 1 1 d . . . . .
C37 C -0.5732(9) -0.0400(9) 0.8747(4) 0.0384(18) Uani 1 1 d . . . . .
H37 H -0.665695 -0.016986 0.867421 0.046 Uiso 1 1 calc R U . . .
C38 C -0.4762(9) -0.0068(9) 0.8294(4) 0.0375(17) Uani 1 1 d . . . . .
H38 H -0.502787 0.038484 0.790860 0.045 Uiso 1 1 calc R U . . .
C39 C -0.2384(7) 0.0024(7) 0.7879(3) 0.0233(13) Uani 1 1 d . . . . .
H39 H -0.145774 -0.027733 0.801765 0.028 Uiso 1 1 calc R U . . .
C40 C -0.2156(8) -0.0611(8) 0.7213(3) 0.0309(15) Uani 1 1 d . . . . .
H40A H -0.194793 -0.157760 0.726350 0.037 Uiso 1 1 calc R U . . .
H40B H -0.302867 -0.018707 0.703683 0.037 Uiso 1 1 calc R U . . .
C41 C -0.1054(8) 0.0425(8) 0.6266(3) 0.0291(14) Uani 1 1 d . . . . .
H41 H -0.189873 0.103586 0.614304 0.035 Uiso 1 1 calc R U . . .
C42 C 0.1200(8) -0.0693(7) 0.6284(3) 0.0303(15) Uani 1 1 d . . . . .
H42 H 0.220062 -0.098821 0.617100 0.036 Uiso 1 1 calc R U . . .
C43 C 0.0442(8) -0.1149(8) 0.6774(3) 0.0299(15) Uani 1 1 d . . . . .
H43 H 0.080963 -0.182671 0.707368 0.036 Uiso 1 1 calc R U . . .
C44 C -0.2499(8) 0.2113(8) 0.8224(4) 0.0321(16) Uani 1 1 d . . . . .
H44A H -0.254203 0.171390 0.866436 0.038 Uiso 1 1 calc R U . . .
H44B H -0.315375 0.306945 0.827280 0.038 Uiso 1 1 calc R U . . .
C45 C 0.0135(9) 0.1414(8) 0.8224(4) 0.0325(15) Uani 1 1 d . . . . .
C46 C -0.1008(8) 0.1998(8) 0.7942(3) 0.0296(15) Uani 1 1 d . . . . .
C47 C -0.0627(8) 0.2492(8) 0.7311(4) 0.0332(16) Uani 1 1 d . . . . .
H47 H -0.128851 0.295468 0.704393 0.040 Uiso 1 1 calc R U . . .
C48 C 0.0781(9) 0.2232(9) 0.7130(4) 0.0370(17) Uani 1 1 d . . . . .
H48 H 0.121499 0.247587 0.672230 0.044 Uiso 1 1 calc R U . . .
C49 C 0.1419(7) 0.4803(7) 0.8392(3) 0.0239(13) Uani 1 1 d . . . . .
C50 C 0.1805(8) 0.3913(7) 0.8893(3) 0.0291(15) Uani 1 1 d . . . . .
C51 C 0.0823(10) 0.3596(9) 0.9358(4) 0.0376(18) Uani 1 1 d . . . . .
H51 H 0.110574 0.300015 0.970197 0.045 Uiso 1 1 calc R U . . .
C52 C -0.0583(8) 0.4183(8) 0.9302(3) 0.0318(16) Uani 1 1 d . . . . .
C53 C -0.0983(10) 0.5031(10) 0.8802(4) 0.044(2) Uani 1 1 d . . . . .
H53 H -0.194532 0.541189 0.876346 0.053 Uiso 1 1 calc R U . . .
C54 C 0.0028(9) 0.5332(10) 0.8351(4) 0.0405(19) Uani 1 1 d . . . . .
H54 H -0.025852 0.592187 0.800502 0.049 Uiso 1 1 calc R U . . .
C55 C 0.2515(7) 0.5137(7) 0.7890(3) 0.0240(13) Uani 1 1 d . . . . .
H55 H 0.340378 0.486983 0.805878 0.029 Uiso 1 1 calc R U . . .
C56 C 0.2831(8) 0.4392(7) 0.7246(3) 0.0294(15) Uani 1 1 d . . . . .
H56A H 0.304910 0.343215 0.733147 0.035 Uiso 1 1 calc R U . . .
H56B H 0.198768 0.475759 0.704651 0.035 Uiso 1 1 calc R U . . .
C57 C 0.3991(8) 0.5330(7) 0.6278(3) 0.0272(14) Uani 1 1 d . . . . .
H57 H 0.315730 0.590349 0.613335 0.033 Uiso 1 1 calc R U . . .
C58 C 0.6211(8) 0.4308(8) 0.6346(3) 0.0305(15) Uani 1 1 d . . . . .
H58 H 0.720792 0.404688 0.625513 0.037 Uiso 1 1 calc R U . . .
C59 C 0.5441(8) 0.3870(7) 0.6839(3) 0.0281(14) Uani 1 1 d . . . . .
H59 H 0.579528 0.323236 0.715730 0.034 Uiso 1 1 calc R U . . .
C60 C 0.2402(8) 0.7285(8) 0.8156(4) 0.0308(15) Uani 1 1 d . . . . .
H60A H 0.232150 0.696460 0.861177 0.037 Uiso 1 1 calc R U . . .
H60B H 0.176473 0.824539 0.816492 0.037 Uiso 1 1 calc R U . . .
C61 C 0.5046(8) 0.6410(8) 0.8145(4) 0.0317(15) Uani 1 1 d . . . . .
C62 C 0.3889(8) 0.7121(7) 0.7881(3) 0.0288(14) Uani 1 1 d . . . . .
C63 C 0.4304(9) 0.7669(8) 0.7264(3) 0.0333(16) Uani 1 1 d . . . . .
H63 H 0.365620 0.821286 0.700604 0.040 Uiso 1 1 calc R U . . .
C64 C 0.5736(9) 0.7322(9) 0.7090(4) 0.0354(16) Uani 1 1 d . . . . .
H64 H 0.619289 0.758117 0.669310 0.042 Uiso 1 1 calc R U . . .
N1 N 0.9759(6) 0.9768(6) 0.4030(3) 0.0268(12) Uani 1 1 d . . . . .
H1N H 0.957443 0.932003 0.437881 0.032 Uiso 1 1 calc R U . . .
N2 N 1.0909(6) 1.0516(6) 0.3223(3) 0.0228(11) Uani 1 1 d . . . . .
N3 N 0.4718(7) 0.4834(6) 0.3999(3) 0.0256(12) Uani 1 1 d . . . . .
H3N H 0.450777 0.441422 0.435455 0.031 Uiso 1 1 calc R U . . .
N4 N 0.5922(6) 0.5530(6) 0.3193(3) 0.0229(11) Uani 1 1 d . . . . .
N5 N -0.0980(6) -0.0437(6) 0.6756(3) 0.0238(11) Uani 1 1 d . . . . .
N6 N 0.0230(7) 0.0286(6) 0.5983(3) 0.0295(13) Uani 1 1 d . . . . .
N7 N 0.4034(6) 0.4531(6) 0.6792(3) 0.0248(11) Uani 1 1 d . . . . .
N8 N 0.5279(7) 0.5199(7) 0.6003(3) 0.0293(12) Uani 1 1 d . . . . .
O1 O 1.2807(5) 0.8609(5) 0.2191(2) 0.0243(9) Uani 1 1 d . . . . .
O2 O 0.7906(5) 0.3504(5) 0.2231(2) 0.0259(10) Uani 1 1 d . . . . .
O3 O -0.2932(5) 0.1433(5) 0.7802(2) 0.0276(10) Uani 1 1 d . . . . .
O4 O 0.1979(5) 0.6536(5) 0.7763(2) 0.0260(10) Uani 1 1 d . . . . .
O5 O 0.9204(5) 0.8623(5) 0.5174(2) 0.0267(9) Uani 1 1 d . . . . .
O6 O 0.6660(6) 0.9416(6) 0.5519(4) 0.0589(19) Uani 1 1 d . . . . .
O7 O 0.8106(6) 0.7215(5) 0.5796(2) 0.0356(10) Uani 1 1 d . . . . .
O8A O 0.7786(19) 0.786(2) 0.4701(5) 0.013(5) Uiso 0.43(8) 1 d . . P . .
O8B O 0.807(3) 0.749(4) 0.4667(8) 0.053(4) Uiso 0.57(8) 1 d . . P . .
O9 O 0.4238(5) 0.3602(5) 0.5116(2) 0.0277(10) Uani 1 1 d . . . . .
O10A O 0.2647(13) 0.3118(13) 0.5961(6) 0.033(3) Uiso 0.394(15) 1 d . . P . .
O10B O 0.2957(8) 0.2361(9) 0.5786(4) 0.030(2) Uiso 0.606(15) 1 d . . P . .
O11A O 0.3313(13) 0.1984(13) 0.4920(7) 0.033(3) Uiso 0.394(15) 1 d . . P . .
O11B O 0.3203(10) 0.2356(11) 0.4633(5) 0.044(2) Uiso 0.606(15) 1 d . . P . .
O12A O 0.1784(9) 0.4345(9) 0.5061(5) 0.011(2) Uiso 0.394(15) 1 d . . P . .
O12B O 0.1667(13) 0.4402(12) 0.5309(8) 0.057(3) Uiso 0.606(15) 1 d . . P . .
O13 O 0.9859(12) 0.6001(9) 0.6663(5) 0.079(3) Uani 1 1 d D . . . .
O14 O 0.3944(5) 0.9553(5) 0.5495(2) 0.0308(10) Uani 1 1 d D . . . .
O15 O 0.8957(5) 0.4519(5) 0.5518(3) 0.0342(10) Uani 1 1 d D . . . .
O16 O 0.8596(5) 0.3142(5) 0.4543(2) 0.0309(10) Uani 1 1 d D . . . .
O17 O 0.6148(5) 0.6281(5) 0.4869(2) 0.0277(10) Uani 1 1 d D . . . .
O18 O 0.3642(6) 0.8073(5) 0.4539(2) 0.0316(10) Uani 1 1 d . . . . .
O19 O 0.5123(6) 0.8786(6) 0.3305(2) 0.0349(12) Uani 1 1 d D . . . .
O20 O 0.6936(5) 0.1893(5) 0.5235(2) 0.0273(9) Uani 1 1 d D . . . .
O21 O 0.1954(5) 0.6863(5) 0.5231(3) 0.0295(9) Uani 1 1 d D . . . .
O22 O 0.4717(9) 0.1175(7) 0.6657(3) 0.0506(16) Uani 1 1 d D . . . .
O23 O 0.0576(6) 0.5665(6) 0.4063(2) 0.0396(12) Uani 1 1 d D . . . .
O24 O 0.5822(6) 0.0313(6) 0.4086(2) 0.0388(12) Uani 1 1 d D . . . .
O25 O 0.0130(7) 0.3827(6) 0.3331(2) 0.0363(12) Uani 1 1 d D . . . .
O26 O 0.1134(5) 0.1312(5) 0.4839(2) 0.0265(9) Uani 1 1 d D . . . .
S1 S 0.81770(19) 0.86343(19) 0.22883(9) 0.0324(4) Uani 1 1 d . . . . .
S2 S 0.32298(19) 0.36812(19) 0.23651(8) 0.0312(4) Uani 1 1 d . . . . .
S3 S 0.1676(2) 0.1404(2) 0.77362(9) 0.0348(4) Uani 1 1 d . . . . .
S4 S 0.6618(2) 0.6355(2) 0.76749(9) 0.0357(4) Uani 1 1 d . . . . .
S5 S 0.79655(15) 0.82319(15) 0.53021(7) 0.0232(3) Uani 1 1 d . . . . .
S6 S 0.29997(15) 0.32125(16) 0.52410(7) 0.0252(3) Uani 1 1 d . . . . .
Cl1A Cl 1.1277(2) 1.1558(4) 0.08698(17) 0.0365(11) Uani 0.865(18) 1 d . . P . .
Cl1B Cl 1.1293(17) 1.198(2) 0.1044(11) 0.034(5) Uiso 0.135(18) 1 d . . P . .
Cl2 Cl 1.6513(2) 1.1481(2) 0.01163(9) 0.0451(5) Uani 1 1 d . . . . .
Cl3 Cl 0.9695(2) 0.9289(2) 0.10301(9) 0.0369(4) Uani 1 1 d . . . . .
Cl4 Cl 0.6383(2) 0.6857(2) 0.10082(11) 0.0483(6) Uani 1 1 d . . . . .
Cl5A Cl 1.1828(4) 0.6114(5) 0.01133(10) 0.0379(11) Uani 0.900(17) 1 d . . P . .
Cl5B Cl 1.136(4) 0.671(4) 0.0111(11) 0.044(6) Uiso 0.100(17) 1 d . . P . .
Cl6 Cl 0.47869(19) 0.44100(18) 0.11407(8) 0.0326(4) Uani 1 1 d . . . . .
Cl7 Cl -0.1354(2) -0.1582(3) 0.91006(10) 0.0457(5) Uani 1 1 d . . . . .
Cl8 Cl -0.6587(3) -0.1473(3) 0.98786(10) 0.0505(6) Uani 1 1 d . . . . .
Cl9 Cl 0.0201(2) 0.0699(2) 0.89935(9) 0.0392(5) Uani 1 1 d . . . . .
Cl1C Cl 0.3583(3) 0.3072(4) 0.8949(2) 0.0397(13) Uani 0.852(18) 1 d . . P . .
Cl1D Cl 0.350(2) 0.356(3) 0.9131(10) 0.047(5) Uiso 0.148(18) 1 d . . P . .
Cl11 Cl -0.1844(2) 0.3824(2) 0.98778(9) 0.0439(5) Uani 1 1 d . . . . .
Cl12 Cl 0.5074(2) 0.5583(2) 0.88870(9) 0.0382(4) Uani 1 1 d . . . . .
H6N H 0.052(12) 0.054(12) 0.566(6) 0.06(3) Uiso 1 1 d . . . . .
H8N H 0.551(11) 0.564(11) 0.572(5) 0.04(3) Uiso 1 1 d . . . . .
H13A H 0.998(13) 0.532(7) 0.635(5) 0.08(4) Uiso 1 1 d D . . . .
H13B H 0.931(10) 0.660(7) 0.642(4) 0.05(3) Uiso 1 1 d D . . . .
H14A H 0.365(9) 1.046(4) 0.565(5) 0.06(3) Uiso 1 1 d D . . . .
H14B H 0.482(4) 0.945(8) 0.552(5) 0.04(2) Uiso 1 1 d D . . . .
H15A H 0.873(12) 0.547(3) 0.546(9) 0.14(7) Uiso 1 1 d D . . . .
H15B H 0.983(4) 0.443(8) 0.550(4) 0.027(19) Uiso 1 1 d D . . . .
H16A H 0.768(7) 0.380(8) 0.475(7) 0.08(4) Uiso 1 1 d D . . . .
H16B H 0.819(10) 0.255(8) 0.465(5) 0.05(3) Uiso 1 1 d D . . . .
H17A H 0.670(9) 0.681(9) 0.485(6) 0.065 Uiso 1 1 d D U . . .
H17B H 0.560(8) 0.694(6) 0.465(4) 0.03(2) Uiso 1 1 d D . . . .
H18A H 0.274(14) 0.887(14) 0.468(7) 0.08(4) Uiso 1 1 d . . . . .
H18B H 0.314(9) 0.758(9) 0.467(4) 0.03(2) Uiso 1 1 d . . . . .
H19A H 0.479(10) 0.838(9) 0.369(3) 0.04(2) Uiso 1 1 d D . . . .
H19B H 0.538(11) 0.920(10) 0.358(4) 0.06(3) Uiso 1 1 d D . . . .
H20A H 0.597(4) 0.243(8) 0.520(5) 0.05(3) Uiso 1 1 d D . . . .
H20B H 0.681(11) 0.128(8) 0.502(7) 0.08(4) Uiso 1 1 d D . . . .
H21A H 0.174(10) 0.631(11) 0.497(7) 0.10(5) Uiso 1 1 d D . . . .
H21B H 0.104(3) 0.738(6) 0.530(3) 0.017(17) Uiso 1 1 d D . . . .
H22A H 0.518(11) 0.054(8) 0.630(4) 0.07(3) Uiso 1 1 d D . . . .
H22B H 0.419(10) 0.172(8) 0.639(4) 0.06(3) Uiso 1 1 d D . . . .
H23A H 0.097(7) 0.498(5) 0.435(3) 0.015(16) Uiso 1 1 d D . . . .
H23B H -0.015(8) 0.611(9) 0.439(3) 0.08(4) Uiso 1 1 d D . . . .
H24C H 0.602(17) -0.011(19) 0.450(4) 0.20(11) Uiso 1 1 d D . . . .
H24D H 0.501(6) 0.087(8) 0.434(4) 0.04(2) Uiso 1 1 d D . . . .
H25A H -0.022(12) 0.347(11) 0.373(3) 0.07(3) Uiso 1 1 d D . . . .
H25B H 0.052(11) 0.413(11) 0.359(4) 0.06(3) Uiso 1 1 d D . . . .
H26A H 0.174(9) 0.180(9) 0.476(6) 0.070 Uiso 1 1 d D U . . .
H26B H 0.053(8) 0.205(6) 0.468(4) 0.04(2) Uiso 1 1 d 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
C1 C6 1.384(11) . ?
C1 C2 1.386(10) . ?
C1 C7 1.511(9) . ?
C2 C3 1.395(10) . ?
C2 Cl1B 1.628(18) . ?
C2 Cl1A 1.757(8) . ?
C3 C4 1.384(12) . ?
C3 H3 0.9500 . ?
C4 C5 1.369(12) . ?
C4 Cl2 1.731(7) . ?
C5 C6 1.388(10) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 O1 1.435(8) . ?
C7 C8 1.517(9) . ?
C7 H7 1.0000 . ?
C8 N2 1.456(8) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 N2 1.334(8) . ?
C9 N1 1.336(9) . ?
C9 H9 0.9500 . ?
C10 C11 1.364(10) . ?
C10 N1 1.368(10) . ?
C10 H10 0.9500 . ?
C11 N2 1.382(9) . ?
C11 H11 0.9500 . ?
C12 O1 1.428(8) . ?
C12 C14 1.507(10) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.355(11) . ?
C13 Cl3 1.703(7) . ?
C13 S1 1.729(7) . ?
C14 C15 1.434(10) . ?
C15 C16 1.338(11) . ?
C15 H15 0.9500 . ?
C16 S1 1.717(8) . ?
C16 H16 0.9500 . ?
C17 C18 1.380(10) . ?
C17 C22 1.401(11) . ?
C17 C23 1.510(9) . ?
C18 C19 1.404(10) . ?
C18 Cl4 1.713(8) . ?
C19 C20 1.378(12) . ?
C19 H19 0.9500 . ?
C20 C21 1.385(12) . ?
C20 Cl5A 1.736(7) . ?
C20 Cl5B 1.80(3) . ?
C21 C22 1.379(11) . ?
C21 H21 0.9500 . ?
C22 H22 0.9500 . ?
C23 O2 1.430(8) . ?
C23 C24 1.533(9) . ?
C23 H23 1.0000 . ?
C24 N4 1.460(7) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C25 N4 1.328(8) . ?
C25 N3 1.343(9) . ?
C25 H25 0.9500 . ?
C26 C27 1.363(10) . ?
C26 N3 1.374(10) . ?
C26 H26 0.9500 . ?
C27 N4 1.382(9) . ?
C27 H27 0.9500 . ?
C28 O2 1.434(9) . ?
C28 C30 1.512(10) . ?
C28 H28A 0.9900 . ?
C28 H28B 0.9900 . ?
C29 C30 1.360(11) . ?
C29 Cl6 1.702(7) . ?
C29 S2 1.729(7) . ?
C30 C31 1.432(10) . ?
C31 C32 1.358(11) . ?
C31 H31 0.9500 . ?
C32 S2 1.704(8) . ?
C32 H32 0.9500 . ?
C33 C34 1.375(10) . ?
C33 C38 1.388(11) . ?
C33 C39 1.520(9) . ?
C34 C35 1.391(10) . ?
C34 Cl7 1.758(8) . ?
C35 C36 1.371(13) . ?
C35 H35 0.9500 . ?
C36 C37 1.388(12) . ?
C36 Cl8 1.735(8) . ?
C37 C38 1.380(11) . ?
C37 H37 0.9500 . ?
C38 H38 0.9500 . ?
C39 O3 1.419(8) . ?
C39 C40 1.526(9) . ?
C39 H39 1.0000 . ?
C40 N5 1.462(9) . ?
C40 H40A 0.9900 . ?
C40 H40B 0.9900 . ?
C41 N6 1.306(10) . ?
C41 N5 1.335(9) . ?
C41 H41 0.9500 . ?
C42 C43 1.352(10) . ?
C42 N6 1.375(10) . ?
C42 H42 0.9500 . ?
C43 N5 1.392(9) . ?
C43 H43 0.9500 . ?
C44 O3 1.441(9) . ?
C44 C46 1.511(10) . ?
C44 H44A 0.9900 . ?
C44 H44B 0.9900 . ?
C45 C46 1.360(12) . ?
C45 S3 1.717(8) . ?
C45 Cl9 1.741(8) . ?
C46 C47 1.427(11) . ?
C47 C48 1.365(11) . ?
C47 H47 0.9500 . ?
C48 S3 1.730(9) . ?
C48 H48 0.9500 . ?
C49 C54 1.365(11) . ?
C49 C50 1.391(9) . ?
C49 C55 1.526(8) . ?
C50 C51 1.393(10) . ?
C50 Cl1C 1.753(8) . ?
C50 Cl1D 1.84(2) . ?
C51 C52 1.388(12) . ?
C51 H51 0.9500 . ?
C52 C53 1.367(12) . ?
C52 Cl11 1.741(7) . ?
C53 C54 1.391(11) . ?
C53 H53 0.9500 . ?
C54 H54 0.9500 . ?
C55 O4 1.426(8) . ?
C55 C56 1.521(9) . ?
C55 H55 1.0000 . ?
C56 N7 1.465(9) . ?
C56 H56A 0.9900 . ?
C56 H56B 0.9900 . ?
C57 N8 1.309(10) . ?
C57 N7 1.334(9) . ?
C57 H57 0.9500 . ?
C58 C59 1.353(10) . ?
C58 N8 1.366(10) . ?
C58 H58 0.9500 . ?
C59 N7 1.388(9) . ?
C59 H59 0.9500 . ?
C60 O4 1.444(9) . ?
C60 C62 1.489(10) . ?
C60 H60A 0.9900 . ?
C60 H60B 0.9900 . ?
C61 C62 1.368(11) . ?
C61 S4 1.715(7) . ?
C61 Cl12 1.739(8) . ?
C62 C63 1.439(10) . ?
C63 C64 1.370(11) . ?
C63 H63 0.9500 . ?
C64 S4 1.734(9) . ?
C64 H64 0.9500 . ?
N1 H1N 0.8800 . ?
N3 H3N 0.8800 . ?
N6 H6N 0.77(13) . ?
N8 H8N 0.79(12) . ?
O5 S5 1.497(5) . ?
O6 S5 1.464(6) . ?
O7 S5 1.448(5) . ?
O8A S5 1.419(10) . ?
O8B S5 1.56(2) . ?
O9 S6 1.497(5) . ?
O10A O10B 0.833(13) . ?
O10A S6 1.475(12) . ?
O10B S6 1.424(8) . ?
O10B O11A 1.805(15) . ?
O11A O11B 0.705(13) . ?
O11A S6 1.422(12) . ?
O11B S6 1.553(10) . ?
O12A O12B 0.508(13) . ?
O12A S6 1.479(9) . ?
O12B S6 1.466(12) . ?
O13 H13A 0.96(2) . ?
O13 H13B 0.89(2) . ?
O14 H14A 0.96(2) . ?
O14 H14B 0.90(2) . ?
O15 H15A 0.97(2) . ?
O15 H15B 0.88(2) . ?
O16 H16A 0.97(2) . ?
O16 H16B 0.90(2) . ?
O17 H17A 0.97(2) . ?
O17 H17B 0.90(2) . ?
O18 H18A 0.99(13) . ?
O18 H18B 0.89(9) . ?
O19 H19A 0.96(2) . ?
O19 H19B 0.90(2) . ?
O20 H20A 0.96(2) . ?
O20 H20B 0.90(2) . ?
O21 H21A 0.96(2) . ?
O21 H21B 0.88(2) . ?
O22 H22A 0.96(2) . ?
O22 H22B 0.89(2) . ?
O23 H23A 0.95(2) . ?
O23 H23B 0.89(2) . ?
O24 H24C 0.97(2) . ?
O24 H24D 0.90(2) . ?
O25 H25A 0.97(2) . ?
O25 H25B 0.90(2) . ?
O26 H26A 0.97(2) . ?
O26 H26B 0.90(2) . ?
Cl1A Cl1B 0.61(3) . ?
Cl5A Cl5B 0.63(4) . ?
Cl1C Cl1D 0.64(3) . ?

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
C6 C1 C2 117.0(6) . . ?
C6 C1 C7 120.2(6) . . ?
C2 C1 C7 122.8(7) . . ?
C1 C2 C3 122.5(7) . . ?
C1 C2 Cl1B 117.9(8) . . ?
C3 C2 Cl1B 116.8(8) . . ?
C1 C2 Cl1A 120.5(6) . . ?
C3 C2 Cl1A 116.9(6) . . ?
Cl1B C2 Cl1A 20.4(9) . . ?
C4 C3 C2 117.5(7) . . ?
C4 C3 H3 121.2 . . ?
C2 C3 H3 121.2 . . ?
C5 C4 C3 122.1(6) . . ?
C5 C4 Cl2 118.7(6) . . ?
C3 C4 Cl2 119.2(6) . . ?
C4 C5 C6 118.5(8) . . ?
C4 C5 H5 120.8 . . ?
C6 C5 H5 120.8 . . ?
C1 C6 C5 122.3(7) . . ?
C1 C6 H6 118.8 . . ?
C5 C6 H6 118.8 . . ?
O1 C7 C1 111.4(5) . . ?
O1 C7 C8 107.2(5) . . ?
C1 C7 C8 109.6(6) . . ?
O1 C7 H7 109.5 . . ?
C1 C7 H7 109.5 . . ?
C8 C7 H7 109.5 . . ?
N2 C8 C7 110.9(6) . . ?
N2 C8 H8A 109.5 . . ?
C7 C8 H8A 109.5 . . ?
N2 C8 H8B 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 108.0 . . ?
N2 C9 N1 108.5(6) . . ?
N2 C9 H9 125.7 . . ?
N1 C9 H9 125.7 . . ?
C11 C10 N1 107.1(6) . . ?
C11 C10 H10 126.4 . . ?
N1 C10 H10 126.4 . . ?
C10 C11 N2 106.9(6) . . ?
C10 C11 H11 126.6 . . ?
N2 C11 H11 126.6 . . ?
O1 C12 C14 111.7(5) . . ?
O1 C12 H12A 109.3 . . ?
C14 C12 H12A 109.3 . . ?
O1 C12 H12B 109.3 . . ?
C14 C12 H12B 109.3 . . ?
H12A C12 H12B 107.9 . . ?
C14 C13 Cl3 127.4(6) . . ?
C14 C13 S1 112.8(5) . . ?
Cl3 C13 S1 119.8(5) . . ?
C13 C14 C15 110.2(7) . . ?
C13 C14 C12 126.9(6) . . ?
C15 C14 C12 122.9(7) . . ?
C16 C15 C14 114.5(7) . . ?
C16 C15 H15 122.8 . . ?
C14 C15 H15 122.8 . . ?
C15 C16 S1 111.5(6) . . ?
C15 C16 H16 124.3 . . ?
S1 C16 H16 124.3 . . ?
C18 C17 C22 117.9(6) . . ?
C18 C17 C23 122.5(6) . . ?
C22 C17 C23 119.6(6) . . ?
C17 C18 C19 121.5(7) . . ?
C17 C18 Cl4 120.3(5) . . ?
C19 C18 Cl4 118.3(6) . . ?
C20 C19 C18 118.5(7) . . ?
C20 C19 H19 120.7 . . ?
C18 C19 H19 120.7 . . ?
C19 C20 C21 121.6(7) . . ?
C19 C20 Cl5A 120.4(6) . . ?
C21 C20 Cl5A 118.0(6) . . ?
C19 C20 Cl5B 103.4(14) . . ?
C21 C20 Cl5B 133.4(13) . . ?
Cl5A C20 Cl5B 20.6(13) . . ?
C22 C21 C20 118.7(8) . . ?
C22 C21 H21 120.7 . . ?
C20 C21 H21 120.7 . . ?
C21 C22 C17 121.8(7) . . ?
C21 C22 H22 119.1 . . ?
C17 C22 H22 119.1 . . ?
O2 C23 C17 112.3(6) . . ?
O2 C23 C24 107.4(5) . . ?
C17 C23 C24 109.3(5) . . ?
O2 C23 H23 109.3 . . ?
C17 C23 H23 109.3 . . ?
C24 C23 H23 109.3 . . ?
N4 C24 C23 110.4(5) . . ?
N4 C24 H24A 109.6 . . ?
C23 C24 H24A 109.6 . . ?
N4 C24 H24B 109.6 . . ?
C23 C24 H24B 109.6 . . ?
H24A C24 H24B 108.1 . . ?
N4 C25 N3 108.5(6) . . ?
N4 C25 H25 125.8 . . ?
N3 C25 H25 125.8 . . ?
C27 C26 N3 107.0(6) . . ?
C27 C26 H26 126.5 . . ?
N3 C26 H26 126.5 . . ?
C26 C27 N4 107.0(6) . . ?
C26 C27 H27 126.5 . . ?
N4 C27 H27 126.5 . . ?
O2 C28 C30 110.7(5) . . ?
O2 C28 H28A 109.5 . . ?
C30 C28 H28A 109.5 . . ?
O2 C28 H28B 109.5 . . ?
C30 C28 H28B 109.5 . . ?
H28A C28 H28B 108.1 . . ?
C30 C29 Cl6 127.1(6) . . ?
C30 C29 S2 113.0(5) . . ?
Cl6 C29 S2 119.9(5) . . ?
C29 C30 C31 110.6(6) . . ?
C29 C30 C28 126.2(6) . . ?
C31 C30 C28 123.2(7) . . ?
C32 C31 C30 113.1(7) . . ?
C32 C31 H31 123.4 . . ?
C30 C31 H31 123.4 . . ?
C31 C32 S2 112.5(5) . . ?
C31 C32 H32 123.8 . . ?
S2 C32 H32 123.8 . . ?
C34 C33 C38 117.0(7) . . ?
C34 C33 C39 123.7(7) . . ?
C38 C33 C39 119.3(6) . . ?
C33 C34 C35 123.1(8) . . ?
C33 C34 Cl7 121.1(6) . . ?
C35 C34 Cl7 115.8(6) . . ?
C36 C35 C34 118.5(7) . . ?
C36 C35 H35 120.8 . . ?
C34 C35 H35 120.8 . . ?
C35 C36 C37 120.0(7) . . ?
C35 C36 Cl8 120.3(6) . . ?
C37 C36 Cl8 119.6(7) . . ?
C38 C37 C36 120.0(8) . . ?
C38 C37 H37 120.0 . . ?
C36 C37 H37 120.0 . . ?
C37 C38 C33 121.3(7) . . ?
C37 C38 H38 119.3 . . ?
C33 C38 H38 119.3 . . ?
O3 C39 C33 111.0(5) . . ?
O3 C39 C40 107.2(5) . . ?
C33 C39 C40 110.2(6) . . ?
O3 C39 H39 109.5 . . ?
C33 C39 H39 109.5 . . ?
C40 C39 H39 109.5 . . ?
N5 C40 C39 110.2(6) . . ?
N5 C40 H40A 109.6 . . ?
C39 C40 H40A 109.6 . . ?
N5 C40 H40B 109.6 . . ?
C39 C40 H40B 109.6 . . ?
H40A C40 H40B 108.1 . . ?
N6 C41 N5 108.5(7) . . ?
N6 C41 H41 125.8 . . ?
N5 C41 H41 125.8 . . ?
C43 C42 N6 106.1(7) . . ?
C43 C42 H42 126.9 . . ?
N6 C42 H42 126.9 . . ?
C42 C43 N5 107.1(6) . . ?
C42 C43 H43 126.5 . . ?
N5 C43 H43 126.5 . . ?
O3 C44 C46 110.5(5) . . ?
O3 C44 H44A 109.6 . . ?
C46 C44 H44A 109.6 . . ?
O3 C44 H44B 109.6 . . ?
C46 C44 H44B 109.6 . . ?
H44A C44 H44B 108.1 . . ?
C46 C45 S3 113.5(6) . . ?
C46 C45 Cl9 128.1(6) . . ?
S3 C45 Cl9 118.3(5) . . ?
C45 C46 C47 110.9(7) . . ?
C45 C46 C44 126.9(7) . . ?
C47 C46 C44 122.1(7) . . ?
C48 C47 C46 113.3(7) . . ?
C48 C47 H47 123.3 . . ?
C46 C47 H47 123.3 . . ?
C47 C48 S3 111.4(6) . . ?
C47 C48 H48 124.3 . . ?
S3 C48 H48 124.3 . . ?
C54 C49 C50 117.5(7) . . ?
C54 C49 C55 121.1(6) . . ?
C50 C49 C55 121.4(6) . . ?
C49 C50 C51 122.5(8) . . ?
C49 C50 Cl1C 121.1(6) . . ?
C51 C50 Cl1C 116.3(6) . . ?
C49 C50 Cl1D 119.4(8) . . ?
C51 C50 Cl1D 115.1(8) . . ?
Cl1C C50 Cl1D 20.2(8) . . ?
C52 C51 C50 117.7(7) . . ?
C52 C51 H51 121.2 . . ?
C50 C51 H51 121.2 . . ?
C53 C52 C51 121.0(7) . . ?
C53 C52 Cl11 120.0(7) . . ?
C51 C52 Cl11 119.1(6) . . ?
C52 C53 C54 119.6(8) . . ?
C52 C53 H53 120.2 . . ?
C54 C53 H53 120.2 . . ?
C49 C54 C53 121.8(8) . . ?
C49 C54 H54 119.1 . . ?
C53 C54 H54 119.1 . . ?
O4 C55 C56 107.7(5) . . ?
O4 C55 C49 110.3(5) . . ?
C56 C55 C49 109.6(6) . . ?
O4 C55 H55 109.7 . . ?
C56 C55 H55 109.7 . . ?
C49 C55 H55 109.7 . . ?
N7 C56 C55 110.5(6) . . ?
N7 C56 H56A 109.6 . . ?
C55 C56 H56A 109.6 . . ?
N7 C56 H56B 109.6 . . ?
C55 C56 H56B 109.6 . . ?
H56A C56 H56B 108.1 . . ?
N8 C57 N7 109.1(6) . . ?
N8 C57 H57 125.4 . . ?
N7 C57 H57 125.4 . . ?
C59 C58 N8 106.7(7) . . ?
C59 C58 H58 126.6 . . ?
N8 C58 H58 126.6 . . ?
C58 C59 N7 107.0(6) . . ?
C58 C59 H59 126.5 . . ?
N7 C59 H59 126.5 . . ?
O4 C60 C62 110.5(6) . . ?
O4 C60 H60A 109.6 . . ?
C62 C60 H60A 109.6 . . ?
O4 C60 H60B 109.6 . . ?
C62 C60 H60B 109.6 . . ?
H60A C60 H60B 108.1 . . ?
C62 C61 S4 114.4(6) . . ?
C62 C61 Cl12 127.3(6) . . ?
S4 C61 Cl12 118.3(5) . . ?
C61 C62 C63 110.3(7) . . ?
C61 C62 C60 126.8(7) . . ?
C63 C62 C60 122.9(7) . . ?
C64 C63 C62 112.8(7) . . ?
C64 C63 H63 123.6 . . ?
C62 C63 H63 123.6 . . ?
C63 C64 S4 112.3(6) . . ?
C63 C64 H64 123.9 . . ?
S4 C64 H64 123.9 . . ?
C9 N1 C10 109.0(6) . . ?
C9 N1 H1N 125.5 . . ?
C10 N1 H1N 125.5 . . ?
C9 N2 C11 108.5(5) . . ?
C9 N2 C8 126.2(6) . . ?
C11 N2 C8 125.3(6) . . ?
C25 N3 C26 108.8(6) . . ?
C25 N3 H3N 125.6 . . ?
C26 N3 H3N 125.6 . . ?
C25 N4 C27 108.8(5) . . ?
C25 N4 C24 125.6(6) . . ?
C27 N4 C24 125.4(6) . . ?
C41 N5 C43 108.0(6) . . ?
C41 N5 C40 127.5(6) . . ?
C43 N5 C40 124.5(6) . . ?
C41 N6 C42 110.3(6) . . ?
C41 N6 H6N 131(9) . . ?
C42 N6 H6N 117(9) . . ?
C57 N7 C59 107.6(6) . . ?
C57 N7 C56 127.2(6) . . ?
C59 N7 C56 125.2(6) . . ?
C57 N8 C58 109.6(6) . . ?
C57 N8 H8N 128(8) . . ?
C58 N8 H8N 122(8) . . ?
C12 O1 C7 113.5(5) . . ?
C23 O2 C28 113.2(5) . . ?
C39 O3 C44 113.0(5) . . ?
C55 O4 C60 113.1(5) . . ?
O10B O10A S6 69.9(10) . . ?
O10A O10B S6 76.7(10) . . ?
O10A O10B O11A 126.6(12) . . ?
S6 O10B O11A 50.6(5) . . ?
O11B O11A S6 87.0(15) . . ?
O11B O11A O10B 136.2(16) . . ?
S6 O11A O10B 50.7(5) . . ?
O11A O11B S6 66.1(13) . . ?
O12B O12A S6 79(2) . . ?
O12A O12B S6 81(2) . . ?
H13A O13 H13B 87(4) . . ?
H14A O14 H14B 85(4) . . ?
H15A O15 H15B 87(4) . . ?
H16A O16 H16B 85(4) . . ?
H17A O17 H17B 86(4) . . ?
H18A O18 H18B 86(9) . . ?
H19A O19 H19B 85(4) . . ?
H20A O20 H20B 83(4) . . ?
H21A O21 H21B 85(4) . . ?
H22A O22 H22B 88(4) . . ?
H23A O23 H23B 91(4) . . ?
H24C O24 H24D 85(4) . . ?
H25A O25 H25B 83(4) . . ?
H26A O26 H26B 83(4) . . ?
C16 S1 C13 91.0(4) . . ?
C32 S2 C29 90.7(4) . . ?
C45 S3 C48 90.8(4) . . ?
C61 S4 C64 90.2(4) . . ?
O8A S5 O7 114.0(8) . . ?
O8A S5 O6 103.0(10) . . ?
O7 S5 O6 109.8(4) . . ?
O8A S5 O5 109.4(4) . . ?
O7 S5 O5 111.0(3) . . ?
O6 S5 O5 109.4(3) . . ?
O8A S5 O8B 14.4(8) . . ?
O7 S5 O8B 103.4(11) . . ?
O6 S5 O8B 116.7(14) . . ?
O5 S5 O8B 106.5(6) . . ?
O11A S6 O10B 78.7(6) . . ?
O11A S6 O12B 125.9(7) . . ?
O10B S6 O12B 110.7(7) . . ?
O11A S6 O10A 111.7(7) . . ?
O10B S6 O10A 33.4(5) . . ?
O12B S6 O10A 86.7(8) . . ?
O11A S6 O12A 113.3(7) . . ?
O10B S6 O12A 126.7(5) . . ?
O12B S6 O12A 19.9(5) . . ?
O10A S6 O12A 106.2(6) . . ?
O11A S6 O9 112.5(5) . . ?
O10B S6 O9 114.1(4) . . ?
O12B S6 O9 110.8(5) . . ?
O10A S6 O9 104.3(5) . . ?
O12A S6 O9 108.2(4) . . ?
O11A S6 O11B 27.0(5) . . ?
O10B S6 O11B 105.1(5) . . ?
O12B S6 O11B 110.0(7) . . ?
O10A S6 O11B 137.0(6) . . ?
O12A S6 O11B 92.6(5) . . ?
O9 S6 O11B 105.8(4) . . ?
Cl1B Cl1A C2 67.8(16) . . ?
Cl1A Cl1B C2 91.7(16) . . ?
Cl5B Cl5A C20 86(2) . . ?
Cl5A Cl5B C20 74(2) . . ?
Cl1D Cl1C C50 87.9(18) . . ?
Cl1C Cl1D C50 71.9(17) . . ?

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
C6 C1 C2 C3 1.3(11) . . . . ?
C7 C1 C2 C3 179.7(7) . . . . ?
C6 C1 C2 Cl1B -159.1(13) . . . . ?
C7 C1 C2 Cl1B 19.2(15) . . . . ?
C6 C1 C2 Cl1A 177.6(6) . . . . ?
C7 C1 C2 Cl1A -4.0(10) . . . . ?
C1 C2 C3 C4 -0.6(12) . . . . ?
Cl1B C2 C3 C4 160.0(13) . . . . ?
Cl1A C2 C3 C4 -177.1(6) . . . . ?
C2 C3 C4 C5 -1.0(12) . . . . ?
C2 C3 C4 Cl2 179.8(6) . . . . ?
C3 C4 C5 C6 1.8(12) . . . . ?
Cl2 C4 C5 C6 -179.0(6) . . . . ?
C2 C1 C6 C5 -0.4(12) . . . . ?
C7 C1 C6 C5 -178.8(7) . . . . ?
C4 C5 C6 C1 -1.1(13) . . . . ?
C6 C1 C7 O1 -57.5(9) . . . . ?
C2 C1 C7 O1 124.2(7) . . . . ?
C6 C1 C7 C8 61.0(9) . . . . ?
C2 C1 C7 C8 -117.3(7) . . . . ?
O1 C7 C8 N2 -67.5(7) . . . . ?
C1 C7 C8 N2 171.4(5) . . . . ?
N1 C10 C11 N2 0.0(8) . . . . ?
Cl3 C13 C14 C15 -177.8(6) . . . . ?
S1 C13 C14 C15 0.4(7) . . . . ?
Cl3 C13 C14 C12 3.9(11) . . . . ?
S1 C13 C14 C12 -178.0(5) . . . . ?
O1 C12 C14 C13 118.2(7) . . . . ?
O1 C12 C14 C15 -60.0(9) . . . . ?
C13 C14 C15 C16 -0.3(9) . . . . ?
C12 C14 C15 C16 178.2(6) . . . . ?
C14 C15 C16 S1 0.1(8) . . . . ?
C22 C17 C18 C19 0.7(11) . . . . ?
C23 C17 C18 C19 179.3(7) . . . . ?
C22 C17 C18 Cl4 -177.1(6) . . . . ?
C23 C17 C18 Cl4 1.6(10) . . . . ?
C17 C18 C19 C20 0.4(11) . . . . ?
Cl4 C18 C19 C20 178.2(6) . . . . ?
C18 C19 C20 C21 -1.6(12) . . . . ?
C18 C19 C20 Cl5A 178.9(6) . . . . ?
C18 C19 C20 Cl5B -168.7(12) . . . . ?
C19 C20 C21 C22 1.6(13) . . . . ?
Cl5A C20 C21 C22 -178.8(7) . . . . ?
Cl5B C20 C21 C22 164.2(18) . . . . ?
C20 C21 C22 C17 -0.4(14) . . . . ?
C18 C17 C22 C21 -0.7(13) . . . . ?
C23 C17 C22 C21 -179.3(8) . . . . ?
C18 C17 C23 O2 136.9(7) . . . . ?
C22 C17 C23 O2 -44.5(9) . . . . ?
C18 C17 C23 C24 -104.0(7) . . . . ?
C22 C17 C23 C24 74.6(9) . . . . ?
O2 C23 C24 N4 -66.6(7) . . . . ?
C17 C23 C24 N4 171.4(5) . . . . ?
N3 C26 C27 N4 -0.9(8) . . . . ?
Cl6 C29 C30 C31 -178.4(5) . . . . ?
S2 C29 C30 C31 1.1(7) . . . . ?
Cl6 C29 C30 C28 2.4(10) . . . . ?
S2 C29 C30 C28 -178.1(5) . . . . ?
O2 C28 C30 C29 110.3(7) . . . . ?
O2 C28 C30 C31 -68.8(9) . . . . ?
C29 C30 C31 C32 -0.9(9) . . . . ?
C28 C30 C31 C32 178.4(7) . . . . ?
C30 C31 C32 S2 0.3(8) . . . . ?
C38 C33 C34 C35 -1.3(12) . . . . ?
C39 C33 C34 C35 -179.8(7) . . . . ?
C38 C33 C34 Cl7 177.9(6) . . . . ?
C39 C33 C34 Cl7 -0.6(10) . . . . ?
C33 C34 C35 C36 -1.5(13) . . . . ?
Cl7 C34 C35 C36 179.2(6) . . . . ?
C34 C35 C36 C37 3.4(13) . . . . ?
C34 C35 C36 Cl8 -178.6(6) . . . . ?
C35 C36 C37 C38 -2.4(13) . . . . ?
Cl8 C36 C37 C38 179.5(7) . . . . ?
C36 C37 C38 C33 -0.5(14) . . . . ?
C34 C33 C38 C37 2.3(12) . . . . ?
C39 C33 C38 C37 -179.1(8) . . . . ?
C34 C33 C39 O3 -122.1(7) . . . . ?
C38 C33 C39 O3 59.4(9) . . . . ?
C34 C33 C39 C40 119.2(8) . . . . ?
C38 C33 C39 C40 -59.2(9) . . . . ?
O3 C39 C40 N5 69.9(7) . . . . ?
C33 C39 C40 N5 -169.1(6) . . . . ?
N6 C42 C43 N5 0.4(8) . . . . ?
S3 C45 C46 C47 -1.7(8) . . . . ?
Cl9 C45 C46 C47 178.6(6) . . . . ?
S3 C45 C46 C44 176.9(6) . . . . ?
Cl9 C45 C46 C44 -2.8(11) . . . . ?
O3 C44 C46 C45 -119.1(8) . . . . ?
O3 C44 C46 C47 59.3(9) . . . . ?
C45 C46 C47 C48 1.9(9) . . . . ?
C44 C46 C47 C48 -176.8(7) . . . . ?
C46 C47 C48 S3 -1.2(9) . . . . ?
C54 C49 C50 C51 -2.6(11) . . . . ?
C55 C49 C50 C51 179.7(7) . . . . ?
C54 C49 C50 Cl1C 174.7(7) . . . . ?
C55 C49 C50 Cl1C -3.0(10) . . . . ?
C54 C49 C50 Cl1D -161.9(13) . . . . ?
C55 C49 C50 Cl1D 20.4(14) . . . . ?
C49 C50 C51 C52 1.4(12) . . . . ?
Cl1C C50 C51 C52 -176.1(6) . . . . ?
Cl1D C50 C51 C52 161.5(13) . . . . ?
C50 C51 C52 C53 0.6(12) . . . . ?
C50 C51 C52 Cl11 -179.4(6) . . . . ?
C51 C52 C53 C54 -1.3(14) . . . . ?
Cl11 C52 C53 C54 178.8(7) . . . . ?
C50 C49 C54 C53 1.9(13) . . . . ?
C55 C49 C54 C53 179.6(8) . . . . ?
C52 C53 C54 C49 0.0(15) . . . . ?
C54 C49 C55 O4 44.1(9) . . . . ?
C50 C49 C55 O4 -138.3(7) . . . . ?
C54 C49 C55 C56 -74.4(9) . . . . ?
C50 C49 C55 C56 103.2(8) . . . . ?
O4 C55 C56 N7 68.8(7) . . . . ?
C49 C55 C56 N7 -171.2(6) . . . . ?
N8 C58 C59 N7 -1.0(8) . . . . ?
S4 C61 C62 C63 -0.8(8) . . . . ?
Cl12 C61 C62 C63 179.2(6) . . . . ?
S4 C61 C62 C60 176.6(6) . . . . ?
Cl12 C61 C62 C60 -3.5(11) . . . . ?
O4 C60 C62 C61 -108.6(8) . . . . ?
O4 C60 C62 C63 68.4(9) . . . . ?
C61 C62 C63 C64 1.4(9) . . . . ?
C60 C62 C63 C64 -176.1(7) . . . . ?
C62 C63 C64 S4 -1.4(9) . . . . ?
N2 C9 N1 C10 0.1(8) . . . . ?
C11 C10 N1 C9 0.0(8) . . . . ?
N1 C9 N2 C11 -0.1(7) . . . . ?
N1 C9 N2 C8 -176.8(6) . . . . ?
C10 C11 N2 C9 0.1(8) . . . . ?
C10 C11 N2 C8 176.8(6) . . . . ?
C7 C8 N2 C9 106.7(7) . . . . ?
C7 C8 N2 C11 -69.4(8) . . . . ?
N4 C25 N3 C26 0.5(8) . . . . ?
C27 C26 N3 C25 0.3(8) . . . . ?
N3 C25 N4 C27 -1.0(7) . . . . ?
N3 C25 N4 C24 -176.5(6) . . . . ?
C26 C27 N4 C25 1.2(8) . . . . ?
C26 C27 N4 C24 176.6(6) . . . . ?
C23 C24 N4 C25 104.6(7) . . . . ?
C23 C24 N4 C27 -70.1(8) . . . . ?
N6 C41 N5 C43 0.0(8) . . . . ?
N6 C41 N5 C40 178.6(6) . . . . ?
C42 C43 N5 C41 -0.2(8) . . . . ?
C42 C43 N5 C40 -178.8(6) . . . . ?
C39 C40 N5 C41 -104.1(8) . . . . ?
C39 C40 N5 C43 74.2(8) . . . . ?
N5 C41 N6 C42 0.2(8) . . . . ?
C43 C42 N6 C41 -0.4(8) . . . . ?
N8 C57 N7 C59 0.4(8) . . . . ?
N8 C57 N7 C56 178.2(6) . . . . ?
C58 C59 N7 C57 0.4(8) . . . . ?
C58 C59 N7 C56 -177.5(6) . . . . ?
C55 C56 N7 C57 -102.9(8) . . . . ?
C55 C56 N7 C59 74.6(8) . . . . ?
N7 C57 N8 C58 -1.0(8) . . . . ?
C59 C58 N8 C57 1.3(8) . . . . ?
C14 C12 O1 C7 -79.6(7) . . . . ?
C1 C7 O1 C12 -93.3(7) . . . . ?
C8 C7 O1 C12 146.7(6) . . . . ?
C17 C23 O2 C28 -95.0(6) . . . . ?
C24 C23 O2 C28 144.8(6) . . . . ?
C30 C28 O2 C23 -79.6(7) . . . . ?
C33 C39 O3 C44 91.6(6) . . . . ?
C40 C39 O3 C44 -147.9(6) . . . . ?
C46 C44 O3 C39 79.4(7) . . . . ?
C56 C55 O4 C60 -145.3(6) . . . . ?
C49 C55 O4 C60 95.1(7) . . . . ?
C62 C60 O4 C55 78.3(7) . . . . ?
S6 O10A O10B O11A -8.7(11) . . . . ?
O10A O10B O11A O11B -7(3) . . . . ?
S6 O10B O11A O11B -18(2) . . . . ?
O10A O10B O11A S6 10.9(14) . . . . ?
O10B O11A O11B S6 13.6(16) . . . . ?
C15 C16 S1 C13 0.1(6) . . . . ?
C14 C13 S1 C16 -0.3(6) . . . . ?
Cl3 C13 S1 C16 178.0(5) . . . . ?
C31 C32 S2 C29 0.3(6) . . . . ?
C30 C29 S2 C32 -0.8(6) . . . . ?
Cl6 C29 S2 C32 178.7(5) . . . . ?
C46 C45 S3 C48 0.8(6) . . . . ?
Cl9 C45 S3 C48 -179.4(5) . . . . ?
C47 C48 S3 C45 0.2(7) . . . . ?
C62 C61 S4 C64 0.0(6) . . . . ?
Cl12 C61 S4 C64 -179.9(5) . . . . ?
C63 C64 S4 C61 0.8(7) . . . . ?
O11B O11A S6 O10B 167.8(15) . . . . ?
O11B O11A S6 O12B 60.4(17) . . . . ?
O10B O11A S6 O12B -107.5(9) . . . . ?
O11B O11A S6 O10A 162.5(13) . . . . ?
O10B O11A S6 O10A -5.3(7) . . . . ?
O11B O11A S6 O12A 42.6(15) . . . . ?
O10B O11A S6 O12A -125.2(6) . . . . ?
O11B O11A S6 O9 -80.5(14) . . . . ?
O10B O11A S6 O9 111.6(4) . . . . ?
O10B O11A S6 O11B -167.8(15) . . . . ?
O10A O10B S6 O11A -171.0(12) . . . . ?
O10A O10B S6 O12B -46.7(12) . . . . ?
O11A O10B S6 O12B 124.3(8) . . . . ?
O11A O10B S6 O10A 171.0(12) . . . . ?
O10A O10B S6 O12A -60.2(12) . . . . ?
O11A O10B S6 O12A 110.8(7) . . . . ?
O10A O10B S6 O9 79.2(10) . . . . ?
O11A O10B S6 O9 -109.8(6) . . . . ?
O10A O10B S6 O11B -165.3(10) . . . . ?
O11A O10B S6 O11B 5.7(7) . . . . ?
O12A O12B S6 O11A -55(2) . . . . ?
O12A O12B S6 O10B -146.4(18) . . . . ?
O12A O12B S6 O10A -170(2) . . . . ?
O12A O12B S6 O9 86.0(19) . . . . ?
O12A O12B S6 O11B -31(2) . . . . ?
O10B O10A S6 O11A 9.5(12) . . . . ?
O10B O10A S6 O12B 137.0(11) . . . . ?
O10B O10A S6 O12A 133.5(9) . . . . ?
O10B O10A S6 O9 -112.3(9) . . . . ?
O10B O10A S6 O11B 21.0(15) . . . . ?
O12B O12A S6 O11A 133.4(19) . . . . ?
O12B O12A S6 O10B 40(2) . . . . ?
O12B O12A S6 O10A 10(2) . . . . ?
O12B O12A S6 O9 -101.1(19) . . . . ?
O12B O12A S6 O11B 151(2) . . . . ?
O11A O11B S6 O10B -12.4(15) . . . . ?
O11A O11B S6 O12B -131.5(14) . . . . ?
O11A O11B S6 O10A -24.1(18) . . . . ?
O11A O11B S6 O12A -141.5(14) . . . . ?
O11A O11B S6 O9 108.7(14) . . . . ?
C1 C2 Cl1A Cl1B 88.5(17) . . . . ?
C3 C2 Cl1A Cl1B -95.0(17) . . . . ?
C1 C2 Cl1B Cl1A -103.0(16) . . . . ?
C3 C2 Cl1B Cl1A 95.5(16) . . . . ?
C19 C20 Cl5A Cl5B 37(2) . . . . ?
C21 C20 Cl5A Cl5B -143(2) . . . . ?
C19 C20 Cl5B Cl5A -148(2) . . . . ?
C21 C20 Cl5B Cl5A 47(3) . . . . ?
C49 C50 Cl1C Cl1D 91.1(18) . . . . ?
C51 C50 Cl1C Cl1D -91.4(18) . . . . ?
C49 C50 Cl1D Cl1C -100.8(19) . . . . ?
C51 C50 Cl1D Cl1C 98.4(17) . . . . ?

_refine_diff_density_max         0.821
_refine_diff_density_min         -0.690
_refine_diff_density_rms         0.117

####################################################################### 
# 
# 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_TCZ_OXAH
_database_code_depnum_ccdc_archive 'CCDC 2296506'
loop_
_audit_author_name
_audit_author_address
'Tejender Thakur'
;CSIR Central Drug Research Institute
India
;
_audit_update_record             
;
2023-09-21 deposited with the CCDC.	2023-11-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/2
_shelx_SHELXL_version_number     2019/2
_chemical_name_systematic        ?
_chemical_name_common            'Tioconazole-oxalate (2:1)salt tetrahydrate'
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C16 H14 Cl3 N2 O S), C2 O4, 4(H2 O)'
_chemical_formula_sum            'C34 H36 Cl6 N4 O10 S2'
_chemical_formula_weight         937.49

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'
Cl Cl 0.3639 0.7018 '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'
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'

_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                   7.65410(10)
_cell_length_b                   15.9993(4)
_cell_length_c                   17.8133(5)
_cell_angle_alpha                73.851(2)
_cell_angle_beta                 78.295(2)
_cell_angle_gamma                85.648(2)
_cell_volume                     2051.33(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    18144
_cell_measurement_theta_min      2.6290
_cell_measurement_theta_max      78.8510

_exptl_crystal_description       plate
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.518
_exptl_crystal_F_000             964
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    5.284
_shelx_estimated_absorpt_T_min   0.505
_shelx_estimated_absorpt_T_max   0.858
_exptl_absorpt_correction_T_min  0.61561
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.88a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_ambient_environment      N~2~
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_type            HyPix
_diffrn_detector_area_resol_mean 10.0000
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0367903000
_diffrn_orient_matrix_UB_12      0.0356608000
_diffrn_orient_matrix_UB_13      -0.0851559000
_diffrn_orient_matrix_UB_21      0.0131369000
_diffrn_orient_matrix_UB_22      -0.0931258000
_diffrn_orient_matrix_UB_23      -0.0096993000
_diffrn_orient_matrix_UB_31      -0.2018460000
_diffrn_orient_matrix_UB_32      -0.0104474000
_diffrn_orient_matrix_UB_33      0.0326156000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -48.00 -21.00   0.50    0.43    --  -91.75  45.00  60.00   54
  2  ω   -102.00 -43.00   0.50    0.43    --  -91.75  77.00   0.00  118
  3  ω    -48.00 -21.00   0.50    0.43    --  -91.75  45.00 -60.00   54
  4  ω    -49.00 -24.00   0.50    0.43    --  -91.75  45.00 -90.00   50
  5  ω    -41.00  26.00   0.50    0.11    --  -47.33  38.00-120.00  134
  6  ω    -16.00  11.00   0.50    0.11    --  -47.33  19.00-180.00   54
  7  ω    -39.00  26.00   0.50    0.11    --  -47.33  38.00   0.00  130
  8  ω    -17.00  20.00   0.50    0.11    --  -47.33  19.00 120.00   74
  9  ω    -18.00  21.00   0.50    0.11    --  -47.33  19.00 150.00   78
 10  ω    -74.00   1.00   0.50    0.11    --  -47.33  96.00  61.00  150
 11  ω    -84.00 -13.00   0.50    0.11    --  -47.33 125.00  90.00  142
 12  ω    -67.00 -41.00   0.50    0.43    --  -91.75  96.00  61.00   52
 13  ω   -147.00-122.00   0.50    0.43    --  -91.75 -96.00 -48.00   50
 14  ω     43.00  72.00   0.50    0.43    --  113.25 -61.00  90.00   58
 15  ω     44.00 107.00   0.50    0.43    --  113.25 -77.00  60.00  126
 16  ω     82.00 107.00   0.50    0.43    --  113.25 -77.00 -90.00   50
 17  ω     43.00  68.00   0.50    0.43    --  113.25 -77.00 -90.00   50
 18  ω     42.00  73.00   0.50    0.43    --  113.25 -61.00  60.00   62
 19  ω     46.00  72.00   0.50    0.43    --  113.25 -61.00 150.00   52
 20  ω     45.00  72.00   0.50    0.43    --  113.25 -61.00   0.00   54
 21  ω     96.00 176.00   0.50    0.43    --  113.25 125.00  90.00  160
 22  ω    106.00 171.00   0.50    0.43    --  113.25  96.00  61.00  130
 23  ω     43.00  71.00   0.50    0.43    --  113.25 -61.00-150.00   56
 24  ω     42.00  67.00   0.50    0.43    --  113.25 -61.00-120.00   50
 25  ω     51.00  76.00   0.50    0.43    --  113.25 -95.00-150.00   50
 26  ω     62.00 111.00   0.50    0.43    --  113.25-125.00 -30.00   98
 27  ω     66.00 106.00   0.50    0.43    --  113.25-110.00  40.82   80
 28  ω     44.00 111.00   0.50    0.43    --  113.25-125.00  90.00  134
 29  ω     68.00 109.00   0.50    0.43    --  113.25-115.00  84.49   82
 30  ω     45.00  70.00   0.50    0.43    --  113.25 -95.00 150.00   50
 31  ω     81.00 106.00   0.50    0.43    --  113.25 -95.00 150.00   50
 32  ω     49.00  85.00   0.50    0.43    --  113.25 -95.00   0.00   72
 33  ω     68.00 103.00   0.50    0.43    --  113.25 -96.00 -48.00   70
 34  ω     79.00 106.00   0.50    0.43    --  113.25 -95.00-120.00   54
 35  ω     42.00  75.00   0.50    0.43    --  113.25 -95.00-120.00   66
 36  ω     46.00  72.00   0.50    0.43    --  113.25 -95.00-180.00   52
 37  ω     80.00 106.00   0.50    0.43    --  113.25 -95.00-150.00   52
 38  ω     79.00 105.00   0.50    0.43    --  113.25 -95.00-180.00   52
 39  ω      1.00  41.00   0.50    0.11    --   47.33 -96.00 -48.00   80
 40  ω     71.00  96.00   0.50    0.43    --  113.25 -95.00  90.00   50
 41  ω     79.00 105.00   0.50    0.43    --  113.25 -95.00 120.00   52
 42  ω    101.00 156.00   0.50    0.43    --  113.25  15.00-120.00  110
 43  ω    114.00 174.00   0.50    0.43    --  113.25  45.00-120.00  120
 44  ω    101.00 176.00   0.50    0.43    --  113.25  45.00 -30.00  150
 45  ω    127.00 164.00   0.50    0.43    --  113.25  45.00 -60.00   74
 46  ω     98.00 173.00   0.50    0.43    --  113.25  61.00   0.00  150
 47  ω    119.00 177.00   0.50    0.43    --  113.25  30.00 -90.00  116
 48  ω    105.00 150.00   0.50    0.43    --  113.25  45.00  60.00   90
 49  ω    118.00 144.00   0.50    0.43    --  113.25  45.00 120.00   52
 50  ω     97.00 170.00   0.50    0.43    --  113.25  61.00 150.00  146
;
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_number            28902
_diffrn_reflns_av_unetI/netI     0.0597
_diffrn_reflns_av_R_equivalents  0.0699
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.630
_diffrn_reflns_theta_max         79.808
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             8721
_reflns_number_gt                7474
_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 1.171.42.88a (Rigaku OD, 2023)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.88a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.88a (Rigaku OD, 2023)'
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_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)+(0.0822P)²+0.4318P] 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         8721
_refine_ls_number_parameters     555
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0555
_refine_ls_R_factor_gt           0.0492
_refine_ls_wR_factor_ref         0.1414
_refine_ls_wR_factor_gt          0.1362
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_restrained_S_all      1.095
_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
C1 C 0.0992(3) 0.04282(14) 0.83131(16) 0.0322(5) Uani 1 1 d . . . . .
C2 C 0.1608(3) -0.01222(15) 0.89645(15) 0.0329(5) Uani 1 1 d . . . . .
C3 C 0.0621(4) -0.08133(16) 0.94841(17) 0.0435(6) Uani 1 1 d . . . . .
H3 H 0.106286 -0.117867 0.992808 0.052 Uiso 1 1 calc R U . . .
C4 C -0.1021(4) -0.09559(17) 0.9338(2) 0.0516(8) Uani 1 1 d . . . . .
C5 C -0.1669(4) -0.04305(19) 0.8692(2) 0.0553(9) Uani 1 1 d . . . . .
H5 H -0.279344 -0.054136 0.859501 0.066 Uiso 1 1 calc R U . . .
C6 C -0.0662(3) 0.02587(17) 0.8186(2) 0.0446(7) Uani 1 1 d . . . . .
H6 H -0.111048 0.062268 0.774303 0.054 Uiso 1 1 calc R U . . .
C7 C 0.2069(3) 0.11767(14) 0.77348(15) 0.0303(5) Uani 1 1 d . . . . .
H7 H 0.288999 0.138858 0.800992 0.036 Uiso 1 1 calc R U . . .
C8 C 0.3149(3) 0.08935(14) 0.70197(16) 0.0318(5) Uani 1 1 d . . . . .
H8A H 0.377466 0.033241 0.720839 0.038 Uiso 1 1 calc R U . . .
H8B H 0.233555 0.080942 0.668120 0.038 Uiso 1 1 calc R U . . .
C9 C 0.4116(3) 0.23410(15) 0.60988(15) 0.0318(5) Uani 1 1 d . . . . .
H9 H 0.298058 0.255533 0.598424 0.038 Uiso 1 1 calc R U . . .
C10 C 0.6971(3) 0.22626(17) 0.61295(17) 0.0368(5) Uani 1 1 d . . . . .
H10 H 0.818582 0.241625 0.603708 0.044 Uiso 1 1 calc R U . . .
C11 C 0.6250(3) 0.14975(16) 0.65783(16) 0.0347(5) Uani 1 1 d . . . . .
H11 H 0.686427 0.100993 0.685918 0.042 Uiso 1 1 calc R U . . .
C12 C 0.0234(3) 0.23942(15) 0.79395(16) 0.0344(5) Uani 1 1 d . . . . .
H12A H 0.120948 0.269230 0.804447 0.041 Uiso 1 1 calc R U . . .
H12B H -0.038775 0.202096 0.845203 0.041 Uiso 1 1 calc R U . . .
C13 C -0.2852(3) 0.30096(16) 0.77754(17) 0.0360(5) Uani 1 1 d . . . . .
C14 C -0.1039(3) 0.30459(15) 0.75604(15) 0.0313(5) Uani 1 1 d . . . . .
C15 C -0.0528(3) 0.37962(15) 0.69130(15) 0.0337(5) Uani 1 1 d . . . . .
H15 H 0.067917 0.393217 0.667263 0.040 Uiso 1 1 calc R U . . .
C16 C -0.1935(4) 0.42965(18) 0.66745(17) 0.0413(6) Uani 1 1 d . . . . .
H16 H -0.182320 0.481895 0.625460 0.050 Uiso 1 1 calc R U . . .
C17 C -0.1630(3) 0.57232(13) 0.80089(12) 0.0227(4) Uani 1 1 d . . . . .
C18 C -0.1222(3) 0.48782(14) 0.84232(13) 0.0239(4) Uani 1 1 d . . . . .
C19 C -0.2522(3) 0.43066(14) 0.89091(13) 0.0263(4) Uani 1 1 d . . . . .
H19 H -0.221486 0.373138 0.918154 0.032 Uiso 1 1 calc R U . . .
C20 C -0.4289(3) 0.46022(14) 0.89850(13) 0.0262(4) Uani 1 1 d . . . . .
C21 C -0.4759(3) 0.54307(14) 0.85771(13) 0.0261(4) Uani 1 1 d . . . . .
H21 H -0.597376 0.561967 0.862799 0.031 Uiso 1 1 calc R U . . .
C22 C -0.3420(3) 0.59805(14) 0.80921(13) 0.0253(4) Uani 1 1 d . . . . .
H22 H -0.373535 0.654945 0.780833 0.030 Uiso 1 1 calc R U . . .
C23 C -0.0173(3) 0.63563(13) 0.75283(12) 0.0228(4) Uani 1 1 d . . . . .
H23 H 0.077295 0.631655 0.785081 0.027 Uiso 1 1 calc R U . . .
C24 C 0.0691(3) 0.61810(15) 0.67336(13) 0.0269(4) Uani 1 1 d . . . . .
H24A H 0.096537 0.555139 0.681128 0.032 Uiso 1 1 calc R U . . .
H24B H -0.013911 0.635953 0.635479 0.032 Uiso 1 1 calc R U . . .
C25 C 0.2451(3) 0.75194(14) 0.60273(13) 0.0273(4) Uani 1 1 d . . . . .
H25 H 0.148988 0.788925 0.586274 0.033 Uiso 1 1 calc R U . . .
C26 C 0.5121(3) 0.70455(18) 0.62381(17) 0.0389(6) Uani 1 1 d . . . . .
H26 H 0.636243 0.703334 0.624033 0.047 Uiso 1 1 calc R U . . .
C27 C 0.4011(3) 0.63701(17) 0.65542(16) 0.0355(5) Uani 1 1 d . . . . .
H27 H 0.431954 0.579369 0.682274 0.043 Uiso 1 1 calc R U . . .
C28 C -0.0993(3) 0.76451(14) 0.79655(13) 0.0268(4) Uani 1 1 d . . . . .
H28A H -0.175420 0.728953 0.844963 0.032 Uiso 1 1 calc R U . . .
H28B H -0.158826 0.822153 0.780958 0.032 Uiso 1 1 calc R U . . .
C29 C 0.1443(3) 0.72508(14) 0.87845(13) 0.0253(4) Uani 1 1 d . . . . .
C30 C 0.0789(3) 0.77602(13) 0.81501(13) 0.0246(4) Uani 1 1 d . . . . .
C31 C 0.2051(3) 0.84011(14) 0.76745(15) 0.0306(5) Uani 1 1 d . . . . .
H31 H 0.184513 0.881440 0.720051 0.037 Uiso 1 1 calc R U . . .
C32 C 0.3573(3) 0.83639(15) 0.79640(16) 0.0326(5) Uani 1 1 d . . . . .
H32 H 0.454654 0.874197 0.771658 0.039 Uiso 1 1 calc R U . . .
C33 C 0.6045(2) 0.50253(14) 0.48870(13) 0.0259(4) Uani 1 1 d . . . . .
C34 C 0.5979(3) 0.98486(16) 0.48682(15) 0.0324(5) Uani 1 1 d . . . . .
Cl1 Cl 0.36982(9) 0.00206(4) 0.91433(4) 0.04281(16) Uani 1 1 d . . . . .
Cl2A Cl -0.248(2) -0.1787(5) 0.9860(11) 0.056(2) Uani 0.53(4) 1 d . . P . .
Cl2B Cl -0.2067(13) -0.1860(3) 1.0079(8) 0.0453(13) Uani 0.47(4) 1 d . . P . .
Cl3 Cl -0.40649(10) 0.22212(5) 0.85095(5) 0.0577(2) Uani 1 1 d . . . . .
Cl4 Cl 0.09906(6) 0.45125(3) 0.83719(3) 0.02919(13) Uani 1 1 d . . . . .
Cl5 Cl -0.59252(7) 0.39097(4) 0.96174(3) 0.03436(14) Uani 1 1 d . . . . .
Cl6 Cl 0.04232(7) 0.63707(4) 0.94935(3) 0.03270(14) Uani 1 1 d . . . . .
S1 S -0.39319(9) 0.38726(5) 0.72212(5) 0.04418(17) Uani 1 1 d . . . . .
S2 S 0.35248(7) 0.75481(4) 0.88342(4) 0.03119(14) Uani 1 1 d . . . . .
N1 N 0.4456(2) 0.15558(12) 0.65527(12) 0.0298(4) Uani 1 1 d . . . . .
N2 N 0.5624(3) 0.27738(13) 0.58334(13) 0.0323(4) Uani 1 1 d . . . . .
N3 N 0.2337(2) 0.66751(12) 0.64136(11) 0.0260(4) Uani 1 1 d . . . . .
N4 N 0.4126(3) 0.77557(14) 0.59116(12) 0.0315(4) Uani 1 1 d . . . . .
O1 O 0.0945(2) 0.18755(10) 0.74033(10) 0.0312(3) Uani 1 1 d . . . . .
O2 O -0.08216(19) 0.72276(9) 0.73321(9) 0.0249(3) Uani 1 1 d . . . . .
O3 O 0.69118(19) 0.43176(10) 0.49894(10) 0.0303(3) Uani 1 1 d . . . . .
O4 O 0.6687(2) 0.57649(11) 0.46222(13) 0.0407(4) Uani 1 1 d . . . . .
O5 O 0.6329(2) 0.90558(12) 0.51614(13) 0.0412(4) Uani 1 1 d . . . . .
O6 O 0.7018(2) 1.04031(12) 0.44083(13) 0.0428(4) Uani 1 1 d . . . . .
O7 O 0.9496(2) 0.63240(13) 0.50676(11) 0.0351(4) Uani 1 1 d . . . . .
O8 O 0.9408(2) 0.80762(13) 0.50802(13) 0.0408(4) Uani 1 1 d . . . . .
O9 O 1.0179(2) 0.96707(14) 0.38486(13) 0.0421(4) Uani 1 1 d . . . . .
O10 O 1.3195(3) 1.06205(13) 0.32533(13) 0.0426(4) Uani 1 1 d . . . . .
H2N H 0.578(5) 0.330(3) 0.552(2) 0.058(10) Uiso 1 1 d . . . . .
H4N H 0.461(5) 0.830(2) 0.568(2) 0.048(9) Uiso 1 1 d . . . . .
H7A H 0.880(5) 0.608(2) 0.493(2) 0.041(8) Uiso 1 1 d . . . . .
H7N H 1.044(5) 0.605(2) 0.5032(19) 0.038(8) Uiso 1 1 d . . . . .
H8C H 0.844(5) 0.831(2) 0.513(2) 0.041(8) Uiso 1 1 d . . . . .
H8D H 0.929(4) 0.755(3) 0.503(2) 0.044(9) Uiso 1 1 d . . . . .
H9A H 0.924(5) 0.993(3) 0.404(2) 0.054(10) Uiso 1 1 d . . . . .
H9B H 1.026(5) 0.922(3) 0.425(3) 0.064(12) Uiso 1 1 d . . . . .
H10A H 1.222(5) 1.035(3) 0.349(2) 0.050(9) Uiso 1 1 d . . . . .
H10B H 1.342(7) 1.083(4) 0.363(4) 0.102(18) 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
C1 C6 1.389(4) . ?
C1 C2 1.391(4) . ?
C1 C7 1.515(3) . ?
C2 C3 1.387(4) . ?
C2 Cl1 1.736(3) . ?
C3 C4 1.381(5) . ?
C3 H3 0.9500 . ?
C4 C5 1.382(5) . ?
C4 Cl2A 1.729(5) . ?
C4 Cl2B 1.778(6) . ?
C5 C6 1.384(4) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 O1 1.425(3) . ?
C7 C8 1.532(3) . ?
C7 H7 1.0000 . ?
C8 N1 1.465(3) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 N2 1.324(3) . ?
C9 N1 1.330(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.349(4) . ?
C10 N2 1.365(3) . ?
C10 H10 0.9500 . ?
C11 N1 1.379(3) . ?
C11 H11 0.9500 . ?
C12 O1 1.435(3) . ?
C12 C14 1.488(3) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.363(3) . ?
C13 Cl3 1.712(3) . ?
C13 S1 1.722(3) . ?
C14 C15 1.429(4) . ?
C15 C16 1.359(4) . ?
C15 H15 0.9500 . ?
C16 S1 1.712(3) . ?
C16 H16 0.9500 . ?
C17 C22 1.391(3) . ?
C17 C18 1.394(3) . ?
C17 C23 1.518(3) . ?
C18 C19 1.387(3) . ?
C18 Cl4 1.742(2) . ?
C19 C20 1.392(3) . ?
C19 H19 0.9500 . ?
C20 C21 1.383(3) . ?
C20 Cl5 1.734(2) . ?
C21 C22 1.388(3) . ?
C21 H21 0.9500 . ?
C22 H22 0.9500 . ?
C23 O2 1.416(2) . ?
C23 C24 1.527(3) . ?
C23 H23 1.0000 . ?
C24 N3 1.465(3) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C25 N4 1.324(3) . ?
C25 N3 1.335(3) . ?
C25 H25 0.9500 . ?
C26 C27 1.347(4) . ?
C26 N4 1.375(3) . ?
C26 H26 0.9500 . ?
C27 N3 1.382(3) . ?
C27 H27 0.9500 . ?
C28 O2 1.443(2) . ?
C28 C30 1.502(3) . ?
C28 H28A 0.9900 . ?
C28 H28B 0.9900 . ?
C29 C30 1.359(3) . ?
C29 Cl6 1.722(2) . ?
C29 S2 1.723(2) . ?
C30 C31 1.427(3) . ?
C31 C32 1.357(4) . ?
C31 H31 0.9500 . ?
C32 S2 1.722(3) . ?
C32 H32 0.9500 . ?
C33 O4 1.244(3) . ?
C33 O3 1.255(3) . ?
C33 C33 1.570(4) 2_666 ?
C34 O6 1.237(3) . ?
C34 O5 1.261(3) . ?
C34 C34 1.559(4) 2_676 ?
Cl2A Cl2B 0.531(11) . ?
N2 H2N 0.88(4) . ?
N4 H4N 0.92(4) . ?
O7 H7A 0.79(4) . ?
O7 H7N 0.82(4) . ?
O8 H8C 0.81(4) . ?
O8 H8D 0.87(4) . ?
O9 H9A 0.86(4) . ?
O9 H9B 0.87(5) . ?
O10 H10A 0.86(4) . ?
O10 H10B 0.89(6) . ?

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
C6 C1 C2 117.7(2) . . ?
C6 C1 C7 119.5(2) . . ?
C2 C1 C7 122.7(2) . . ?
C3 C2 C1 122.2(3) . . ?
C3 C2 Cl1 117.2(2) . . ?
C1 C2 Cl1 120.54(18) . . ?
C4 C3 C2 118.2(3) . . ?
C4 C3 H3 120.9 . . ?
C2 C3 H3 120.9 . . ?
C3 C4 C5 121.3(2) . . ?
C3 C4 Cl2A 127.9(9) . . ?
C5 C4 Cl2A 110.7(9) . . ?
C3 C4 Cl2B 110.8(6) . . ?
C5 C4 Cl2B 127.9(6) . . ?
Cl2A C4 Cl2B 17.4(4) . . ?
C4 C5 C6 119.3(3) . . ?
C4 C5 H5 120.3 . . ?
C6 C5 H5 120.3 . . ?
C5 C6 C1 121.2(3) . . ?
C5 C6 H6 119.4 . . ?
C1 C6 H6 119.4 . . ?
O1 C7 C1 111.58(18) . . ?
O1 C7 C8 104.99(19) . . ?
C1 C7 C8 110.63(18) . . ?
O1 C7 H7 109.8 . . ?
C1 C7 H7 109.8 . . ?
C8 C7 H7 109.8 . . ?
N1 C8 C7 110.05(18) . . ?
N1 C8 H8A 109.6 . . ?
C7 C8 H8A 109.6 . . ?
N1 C8 H8B 109.6 . . ?
C7 C8 H8B 109.6 . . ?
H8A C8 H8B 108.2 . . ?
N2 C9 N1 108.7(2) . . ?
N2 C9 H9 125.7 . . ?
N1 C9 H9 125.7 . . ?
C11 C10 N2 107.0(2) . . ?
C11 C10 H10 126.5 . . ?
N2 C10 H10 126.5 . . ?
C10 C11 N1 107.2(2) . . ?
C10 C11 H11 126.4 . . ?
N1 C11 H11 126.4 . . ?
O1 C12 C14 107.8(2) . . ?
O1 C12 H12A 110.1 . . ?
C14 C12 H12A 110.1 . . ?
O1 C12 H12B 110.1 . . ?
C14 C12 H12B 110.1 . . ?
H12A C12 H12B 108.5 . . ?
C14 C13 Cl3 127.0(2) . . ?
C14 C13 S1 113.2(2) . . ?
Cl3 C13 S1 119.86(15) . . ?
C13 C14 C15 110.4(2) . . ?
C13 C14 C12 125.0(2) . . ?
C15 C14 C12 124.6(2) . . ?
C16 C15 C14 113.5(2) . . ?
C16 C15 H15 123.2 . . ?
C14 C15 H15 123.2 . . ?
C15 C16 S1 111.9(2) . . ?
C15 C16 H16 124.0 . . ?
S1 C16 H16 124.0 . . ?
C22 C17 C18 117.38(19) . . ?
C22 C17 C23 121.17(19) . . ?
C18 C17 C23 121.34(18) . . ?
C19 C18 C17 122.44(19) . . ?
C19 C18 Cl4 117.19(16) . . ?
C17 C18 Cl4 120.34(16) . . ?
C18 C19 C20 117.9(2) . . ?
C18 C19 H19 121.0 . . ?
C20 C19 H19 121.0 . . ?
C21 C20 C19 121.7(2) . . ?
C21 C20 Cl5 119.78(17) . . ?
C19 C20 Cl5 118.56(17) . . ?
C20 C21 C22 118.66(19) . . ?
C20 C21 H21 120.7 . . ?
C22 C21 H21 120.7 . . ?
C21 C22 C17 121.9(2) . . ?
C21 C22 H22 119.0 . . ?
C17 C22 H22 119.0 . . ?
O2 C23 C17 112.26(16) . . ?
O2 C23 C24 105.28(17) . . ?
C17 C23 C24 113.53(16) . . ?
O2 C23 H23 108.5 . . ?
C17 C23 H23 108.5 . . ?
C24 C23 H23 108.5 . . ?
N3 C24 C23 108.95(17) . . ?
N3 C24 H24A 109.9 . . ?
C23 C24 H24A 109.9 . . ?
N3 C24 H24B 109.9 . . ?
C23 C24 H24B 109.9 . . ?
H24A C24 H24B 108.3 . . ?
N4 C25 N3 108.69(19) . . ?
N4 C25 H25 125.7 . . ?
N3 C25 H25 125.7 . . ?
C27 C26 N4 107.4(2) . . ?
C27 C26 H26 126.3 . . ?
N4 C26 H26 126.3 . . ?
C26 C27 N3 106.9(2) . . ?
C26 C27 H27 126.5 . . ?
N3 C27 H27 126.5 . . ?
O2 C28 C30 111.77(16) . . ?
O2 C28 H28A 109.3 . . ?
C30 C28 H28A 109.3 . . ?
O2 C28 H28B 109.3 . . ?
C30 C28 H28B 109.3 . . ?
H28A C28 H28B 107.9 . . ?
C30 C29 Cl6 126.75(17) . . ?
C30 C29 S2 113.48(17) . . ?
Cl6 C29 S2 119.77(13) . . ?
C29 C30 C31 110.56(19) . . ?
C29 C30 C28 124.5(2) . . ?
C31 C30 C28 124.9(2) . . ?
C32 C31 C30 113.6(2) . . ?
C32 C31 H31 123.2 . . ?
C30 C31 H31 123.2 . . ?
C31 C32 S2 111.81(17) . . ?
C31 C32 H32 124.1 . . ?
S2 C32 H32 124.1 . . ?
O4 C33 O3 126.02(18) . . ?
O4 C33 C33 116.9(2) . 2_666 ?
O3 C33 C33 117.1(2) . 2_666 ?
O6 C34 O5 127.1(2) . . ?
O6 C34 C34 117.4(3) . 2_676 ?
O5 C34 C34 115.5(3) . 2_676 ?
Cl2B Cl2A C4 86.6(13) . . ?
Cl2A Cl2B C4 76.1(10) . . ?
C16 S1 C13 90.94(13) . . ?
C32 S2 C29 90.54(11) . . ?
C9 N1 C11 108.07(19) . . ?
C9 N1 C8 126.85(19) . . ?
C11 N1 C8 124.8(2) . . ?
C9 N2 C10 109.1(2) . . ?
C9 N2 H2N 127(2) . . ?
C10 N2 H2N 123(2) . . ?
C25 N3 C27 108.26(19) . . ?
C25 N3 C24 126.15(18) . . ?
C27 N3 C24 125.1(2) . . ?
C25 N4 C26 108.7(2) . . ?
C25 N4 H4N 129(2) . . ?
C26 N4 H4N 122(2) . . ?
C7 O1 C12 112.76(19) . . ?
C23 O2 C28 114.00(16) . . ?
H7A O7 H7N 107(3) . . ?
H8C O8 H8D 109(3) . . ?
H9A O9 H9B 101(4) . . ?
H10A O10 H10B 101(4) . . ?

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
C6 C1 C2 C3 -0.9(3) . . . . ?
C7 C1 C2 C3 -179.1(2) . . . . ?
C6 C1 C2 Cl1 177.55(19) . . . . ?
C7 C1 C2 Cl1 -0.6(3) . . . . ?
C1 C2 C3 C4 0.5(3) . . . . ?
Cl1 C2 C3 C4 -177.97(18) . . . . ?
C2 C3 C4 C5 0.4(4) . . . . ?
C2 C3 C4 Cl2A 177.1(3) . . . . ?
C2 C3 C4 Cl2B -179.3(3) . . . . ?
C3 C4 C5 C6 -0.8(4) . . . . ?
Cl2A C4 C5 C6 -178.1(3) . . . . ?
Cl2B C4 C5 C6 178.7(3) . . . . ?
C4 C5 C6 C1 0.5(4) . . . . ?
C2 C1 C6 C5 0.4(4) . . . . ?
C7 C1 C6 C5 178.6(2) . . . . ?
C6 C1 C7 O1 32.3(3) . . . . ?
C2 C1 C7 O1 -149.6(2) . . . . ?
C6 C1 C7 C8 -84.2(3) . . . . ?
C2 C1 C7 C8 93.9(3) . . . . ?
O1 C7 C8 N1 71.2(2) . . . . ?
C1 C7 C8 N1 -168.26(19) . . . . ?
N2 C10 C11 N1 -0.3(3) . . . . ?
Cl3 C13 C14 C15 179.02(18) . . . . ?
S1 C13 C14 C15 -1.0(3) . . . . ?
Cl3 C13 C14 C12 -0.5(4) . . . . ?
S1 C13 C14 C12 179.44(18) . . . . ?
O1 C12 C14 C13 105.5(3) . . . . ?
O1 C12 C14 C15 -74.0(3) . . . . ?
C13 C14 C15 C16 0.9(3) . . . . ?
C12 C14 C15 C16 -179.5(2) . . . . ?
C14 C15 C16 S1 -0.4(3) . . . . ?
C22 C17 C18 C19 -0.6(3) . . . . ?
C23 C17 C18 C19 175.58(19) . . . . ?
C22 C17 C18 Cl4 -178.40(15) . . . . ?
C23 C17 C18 Cl4 -2.2(3) . . . . ?
C17 C18 C19 C20 -0.7(3) . . . . ?
Cl4 C18 C19 C20 177.15(16) . . . . ?
C18 C19 C20 C21 1.6(3) . . . . ?
C18 C19 C20 Cl5 -177.75(16) . . . . ?
C19 C20 C21 C22 -1.1(3) . . . . ?
Cl5 C20 C21 C22 178.22(16) . . . . ?
C20 C21 C22 C17 -0.3(3) . . . . ?
C18 C17 C22 C21 1.1(3) . . . . ?
C23 C17 C22 C21 -175.08(19) . . . . ?
C22 C17 C23 O2 11.7(3) . . . . ?
C18 C17 C23 O2 -164.37(17) . . . . ?
C22 C17 C23 C24 -107.6(2) . . . . ?
C18 C17 C23 C24 76.4(2) . . . . ?
O2 C23 C24 N3 70.6(2) . . . . ?
C17 C23 C24 N3 -166.17(17) . . . . ?
N4 C26 C27 N3 0.3(3) . . . . ?
Cl6 C29 C30 C31 -177.29(16) . . . . ?
S2 C29 C30 C31 1.7(2) . . . . ?
Cl6 C29 C30 C28 1.1(3) . . . . ?
S2 C29 C30 C28 -179.94(15) . . . . ?
O2 C28 C30 C29 -102.5(2) . . . . ?
O2 C28 C30 C31 75.7(2) . . . . ?
C29 C30 C31 C32 -0.8(3) . . . . ?
C28 C30 C31 C32 -179.20(19) . . . . ?
C30 C31 C32 S2 -0.4(2) . . . . ?
C3 C4 Cl2A Cl2B 11.4(11) . . . . ?
C5 C4 Cl2A Cl2B -171.6(10) . . . . ?
C3 C4 Cl2B Cl2A -170.4(9) . . . . ?
C5 C4 Cl2B Cl2A 10.0(11) . . . . ?
C15 C16 S1 C13 -0.1(2) . . . . ?
C14 C13 S1 C16 0.7(2) . . . . ?
Cl3 C13 S1 C16 -179.35(16) . . . . ?
C31 C32 S2 C29 1.11(18) . . . . ?
C30 C29 S2 C32 -1.62(17) . . . . ?
Cl6 C29 S2 C32 177.42(14) . . . . ?
N2 C9 N1 C11 0.5(3) . . . . ?
N2 C9 N1 C8 174.4(2) . . . . ?
C10 C11 N1 C9 -0.1(3) . . . . ?
C10 C11 N1 C8 -174.1(2) . . . . ?
C7 C8 N1 C9 -71.1(3) . . . . ?
C7 C8 N1 C11 101.8(2) . . . . ?
N1 C9 N2 C10 -0.8(3) . . . . ?
C11 C10 N2 C9 0.7(3) . . . . ?
N4 C25 N3 C27 0.7(3) . . . . ?
N4 C25 N3 C24 172.8(2) . . . . ?
C26 C27 N3 C25 -0.6(3) . . . . ?
C26 C27 N3 C24 -172.9(2) . . . . ?
C23 C24 N3 C25 -80.1(3) . . . . ?
C23 C24 N3 C27 90.8(3) . . . . ?
N3 C25 N4 C26 -0.5(3) . . . . ?
C27 C26 N4 C25 0.1(3) . . . . ?
C1 C7 O1 C12 77.9(2) . . . . ?
C8 C7 O1 C12 -162.25(18) . . . . ?
C14 C12 O1 C7 -174.84(18) . . . . ?
C17 C23 O2 C28 81.0(2) . . . . ?
C24 C23 O2 C28 -155.03(16) . . . . ?
C30 C28 O2 C23 65.8(2) . . . . ?

_refine_diff_density_max         0.543
_refine_diff_density_min         -0.498
_refine_diff_density_rms         0.080

####################################################################### 
# 
# 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_TCZ-FUMH1
_database_code_depnum_ccdc_archive 'CCDC 2285609'
loop_
_audit_author_name
_audit_author_address
'Tejender Thakur'
;CSIR Central Drug Research Institute
India
;
_audit_update_record             
;
2023-07-31 deposited with the CCDC.	2023-11-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            'Tioconazole-Fumerate salt monohydrate'
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H14 Cl3 N2 O S, C4 H3 O4, O'
_chemical_formula_sum            'C20 H17 Cl3 N2 O6 S'
_chemical_formula_weight         519.77

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'
Cl Cl 0.3639 0.7018 '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                   7.4874(2)
_cell_length_b                   8.0833(3)
_cell_length_c                   19.8791(5)
_cell_angle_alpha                94.572(2)
_cell_angle_beta                 98.318(2)
_cell_angle_gamma                94.709(3)
_cell_volume                     1181.34(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    13045
_cell_measurement_theta_min      2.2500
_cell_measurement_theta_max      71.9910

_exptl_crystal_description       Block
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.461
_exptl_crystal_F_000             532
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.410
_exptl_crystal_size_mid          0.380
_exptl_crystal_size_min          0.330
_exptl_absorpt_coefficient_mu    4.684
_shelx_estimated_absorpt_T_min   0.250
_shelx_estimated_absorpt_T_max   0.307
_exptl_absorpt_correction_T_min  0.44547
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_source_power             0.0
_diffrn_source_voltage           50.0
_diffrn_source_current           0.6
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   MicroMax003_Cu
_diffrn_radiation_monochromator  Confocal
_diffrn_measurement_specimen_support Loop
_diffrn_detector                 CCD
_diffrn_measurement_device       
;
AFC12 (Right): Kappa 3 circle
;
_diffrn_measurement_device_type  
;
Rigaku Saturn724+ (4x4 bin mode)
;
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -130.00 -10.00   1.00    4.00    --  -40.00 -72.00   0.00  120
  2  ω   -130.00 -10.00   1.00    4.00    --  -40.00 -72.00  70.00  120
  3  ω   -130.00 -10.00   1.00    4.00    --  -40.00 -72.00 140.00  120
  4  ω   -130.00 -10.00   1.00    4.00    --  -40.00 -72.00 210.00  120
  5  ω   -130.00 -10.00   1.00    4.00    --  -40.00 -72.00 280.00  120
  6  ω   -130.00  50.00   1.00    4.00    --  -40.00   0.00   0.00  180
  7  ω   -100.00  20.00   1.00    4.00    --  -70.00  72.00   0.00  120
  8  ω   -100.00  20.00   1.00    4.00    --  -70.00  72.00  70.00  120
  9  ω   -100.00  20.00   1.00    4.00    --  -70.00  72.00 140.00  120
 10  ω   -100.00  20.00   1.00    4.00    --  -70.00  72.00 210.00  120
 11  ω   -100.00  20.00   1.00    4.00    --  -70.00  72.00 280.00  120
 12  ω   -160.00  20.00   1.00    4.00    --  -70.00   0.00   0.00  180
 13  ω   -190.00 -70.00   1.00    4.00    -- -100.00 -72.00   0.00  120
 14  ω   -190.00 -70.00   1.00    4.00    -- -100.00 -72.00  70.00  120
 15  ω   -190.00 -70.00   1.00    4.00    -- -100.00 -72.00 140.00  120
 16  ω   -190.00 -70.00   1.00    4.00    -- -100.00 -72.00 210.00  120
 17  ω   -190.00 -70.00   1.00    4.00    -- -100.00 -72.00 280.00  120
 18  ω   -130.00 -10.00   1.00    4.00    -- -100.00  72.00   0.00  120
 19  ω   -130.00 -10.00   1.00    4.00    -- -100.00  72.00  70.00  120
 20  ω   -130.00 -10.00   1.00    4.00    -- -100.00  72.00 140.00  120
 21  ω   -130.00 -10.00   1.00    4.00    -- -100.00  72.00 210.00  120
 22  ω   -130.00 -10.00   1.00    4.00    -- -100.00  72.00 280.00  120
 23  ω   -190.00 -10.00   1.00    4.00    -- -100.00   0.00   0.00  180
;
_diffrn_reflns_number            23733
_diffrn_reflns_av_unetI/netI     0.0639
_diffrn_reflns_av_R_equivalents  0.1204
_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       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.256
_diffrn_reflns_theta_max         72.787
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.934
_diffrn_measured_fraction_theta_full 0.962
_diffrn_reflns_Laue_measured_fraction_max 0.934
_diffrn_reflns_Laue_measured_fraction_full 0.962
_diffrn_reflns_point_group_measured_fraction_max 0.934
_diffrn_reflns_point_group_measured_fraction_full 0.962
_reflns_number_total             4386
_reflns_number_gt                3561
_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       'CrystalClear-SM Expert 2.1 b28 (Rigaku, 2013)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_structure_solution    'SHELXS-2013/1 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'
_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)+(0.1222P)²+0.5265P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   direct
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.0155(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4386
_refine_ls_number_parameters     296
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0836
_refine_ls_R_factor_gt           0.0726
_refine_ls_wR_factor_ref         0.2029
_refine_ls_wR_factor_gt          0.1881
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.047
_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
C1 C 0.9293(4) 0.3000(4) 0.35023(15) 0.0470(7) Uani 1 1 d . . . . .
C2 C 0.8351(4) 0.2516(4) 0.40172(16) 0.0504(7) Uani 1 1 d . . . . .
C3 C 0.7687(4) 0.3660(4) 0.44514(16) 0.0555(8) Uani 1 1 d . . . . .
H3 H 0.704483 0.331015 0.478967 0.067 Uiso 1 1 calc R U . . .
C4 C 0.8002(5) 0.5317(4) 0.43691(16) 0.0559(8) Uani 1 1 d . . . . .
C5 C 0.8971(5) 0.5856(4) 0.38817(19) 0.0655(9) Uani 1 1 d . . . . .
H5 H 0.919996 0.698893 0.384167 0.079 Uiso 1 1 calc R U . . .
C6 C 0.9606(5) 0.4685(4) 0.34480(17) 0.0599(8) Uani 1 1 d . . . . .
H6 H 1.025723 0.504528 0.311381 0.072 Uiso 1 1 calc R U . . .
C7 C 0.9892(4) 0.1717(4) 0.30007(15) 0.0489(7) Uani 1 1 d . . . . .
H7 H 1.025432 0.075247 0.323834 0.059 Uiso 1 1 calc R U . . .
C8 C 0.8332(5) 0.1164(4) 0.24352(18) 0.0616(9) Uani 1 1 d . . . . .
H8A H 0.723563 0.092935 0.263142 0.074 Uiso 1 1 calc R U . . .
H8B H 0.813884 0.205773 0.214270 0.074 Uiso 1 1 calc R U . . .
C9 C 0.9252(5) -0.0368(5) 0.14239(19) 0.0696(10) Uani 1 1 d . . . . .
H9 H 0.943329 0.054552 0.117730 0.084 Uiso 1 1 calc R U . . .
C10 C 0.9108(5) -0.2906(5) 0.1722(2) 0.0715(10) Uani 1 1 d . . . . .
H10 H 0.916561 -0.405216 0.171565 0.086 Uiso 1 1 calc R U . . .
C11 C 0.8612(5) -0.1910(5) 0.22155(19) 0.0660(9) Uani 1 1 d . . . . .
H11 H 0.827114 -0.224094 0.261971 0.079 Uiso 1 1 calc R U . . .
C12 C 1.3092(4) 0.2051(4) 0.30299(17) 0.0557(8) Uani 1 1 d . . . . .
H12A H 1.315196 0.230453 0.351831 0.067 Uiso 1 1 calc R U . . .
H12B H 1.403139 0.276819 0.288003 0.067 Uiso 1 1 calc R U . . .
C13 C 1.3512(5) -0.0889(5) 0.33362(19) 0.0642(9) Uani 1 1 d . . . . .
C14 C 1.3436(4) 0.0273(4) 0.28866(17) 0.0534(8) Uani 1 1 d . . . . .
C15 C 1.3724(4) -0.0424(5) 0.22312(19) 0.0651(9) Uani 1 1 d . . . . .
H15 H 1.371271 0.018114 0.185207 0.078 Uiso 1 1 calc R U . . .
C16 C 1.4014(5) -0.2050(6) 0.2221(2) 0.0792(12) Uani 1 1 d . . . . .
H16 H 1.422359 -0.268922 0.183471 0.095 Uiso 1 1 calc R U . . .
C17 C 0.9867(4) 0.3219(4) 0.04562(15) 0.0526(8) Uani 1 1 d . . . . .
C18 C 1.1905(4) 0.3411(5) 0.05669(17) 0.0607(9) Uani 1 1 d . . . . .
H18 H 1.249707 0.336381 0.018650 0.073 Uiso 1 1 calc R U . . .
C19 C 1.2883(4) 0.3640(5) 0.11717(16) 0.0565(8) Uani 1 1 d . . . . .
H19 H 1.227994 0.374310 0.154806 0.068 Uiso 1 1 calc R U . . .
C20 C 1.4888(4) 0.3746(5) 0.12988(17) 0.0578(8) Uani 1 1 d . . . . .
N1 N 0.8688(4) -0.0323(4) 0.20277(13) 0.0555(7) Uani 1 1 d . . . . .
N2 N 0.9514(4) -0.1920(4) 0.12297(16) 0.0703(9) Uani 1 1 d . . . . .
O1 O 1.1362(3) 0.2389(3) 0.26923(10) 0.0549(6) Uani 1 1 d . . . . .
O2 O 0.9079(3) 0.2772(4) -0.01331(12) 0.0803(8) Uani 1 1 d . . . . .
O3 O 0.9081(3) 0.3499(3) 0.09599(11) 0.0639(6) Uani 1 1 d . . . . .
O4 O 1.5628(3) 0.3537(5) 0.07487(13) 0.0922(11) Uani 1 1 d . . . . .
H4 H 1.683(9) 0.359(8) 0.0863(9) 0.138 Uiso 1 1 calc R U . . .
O5 O 1.5730(3) 0.4017(4) 0.18668(13) 0.0764(8) Uani 1 1 d . . . . .
S1 S 1.39512(15) -0.28025(13) 0.29958(7) 0.0850(4) Uani 1 1 d . . . . .
Cl1 Cl 0.79893(14) 0.04206(11) 0.41437(5) 0.0757(4) Uani 1 1 d . . . . .
Cl2 Cl 0.71665(16) 0.67664(12) 0.49098(5) 0.0796(4) Uani 1 1 d . . . . .
Cl3 Cl 1.31850(15) -0.06299(15) 0.41796(5) 0.0830(4) Uani 1 1 d . . . . .
O6A O 1.5285(17) 0.202(2) -0.0652(6) 0.130(6) Uiso 0.40(2) 1 d . . P . .
O6B O 1.5449(15) 0.083(2) -0.0570(5) 0.173(5) Uiso 0.60(2) 1 d . . P . .
H2N H 1.009(7) -0.222(7) 0.079(3) 0.111(16) 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
C1 C6 1.378(5) . ?
C1 C2 1.388(4) . ?
C1 C7 1.521(4) . ?
C2 C3 1.385(4) . ?
C2 Cl1 1.737(3) . ?
C3 C4 1.368(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.369(5) . ?
C4 Cl2 1.742(3) . ?
C5 C6 1.388(5) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 O1 1.426(4) . ?
C7 C8 1.511(4) . ?
C7 H7 0.9800 . ?
C8 N1 1.460(4) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 N2 1.322(5) . ?
C9 N1 1.328(5) . ?
C9 H9 0.9300 . ?
C10 C11 1.333(5) . ?
C10 N2 1.363(6) . ?
C10 H10 0.9300 . ?
C11 N1 1.363(5) . ?
C11 H11 0.9300 . ?
C12 O1 1.428(4) . ?
C12 C14 1.493(5) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.346(5) . ?
C13 S1 1.715(4) . ?
C13 Cl3 1.728(4) . ?
C14 C15 1.430(5) . ?
C15 C16 1.349(6) . ?
C15 H15 0.9300 . ?
C16 S1 1.706(5) . ?
C16 H16 0.9300 . ?
C17 O2 1.244(4) . ?
C17 O3 1.248(4) . ?
C17 C18 1.504(4) . ?
C18 C19 1.305(5) . ?
C18 H18 0.9300 . ?
C19 C20 1.480(4) . ?
C19 H19 0.9300 . ?
C20 O5 1.205(4) . ?
C20 O4 1.301(4) . ?
N2 H2N 1.04(6) . ?
O4 H4 0.90(7) . ?
O6A O6B 1.006(14) . ?

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
C6 C1 C2 117.5(3) . . ?
C6 C1 C7 121.3(3) . . ?
C2 C1 C7 121.1(3) . . ?
C3 C2 C1 122.2(3) . . ?
C3 C2 Cl1 117.5(2) . . ?
C1 C2 Cl1 120.3(2) . . ?
C4 C3 C2 118.2(3) . . ?
C4 C3 H3 120.9 . . ?
C2 C3 H3 120.9 . . ?
C3 C4 C5 121.7(3) . . ?
C3 C4 Cl2 118.6(3) . . ?
C5 C4 Cl2 119.7(3) . . ?
C4 C5 C6 119.0(3) . . ?
C4 C5 H5 120.5 . . ?
C6 C5 H5 120.5 . . ?
C1 C6 C5 121.4(3) . . ?
C1 C6 H6 119.3 . . ?
C5 C6 H6 119.3 . . ?
O1 C7 C8 107.4(2) . . ?
O1 C7 C1 111.8(2) . . ?
C8 C7 C1 109.1(2) . . ?
O1 C7 H7 109.5 . . ?
C8 C7 H7 109.5 . . ?
C1 C7 H7 109.5 . . ?
N1 C8 C7 111.3(2) . . ?
N1 C8 H8A 109.4 . . ?
C7 C8 H8A 109.4 . . ?
N1 C8 H8B 109.4 . . ?
C7 C8 H8B 109.4 . . ?
H8A C8 H8B 108.0 . . ?
N2 C9 N1 109.0(3) . . ?
N2 C9 H9 125.5 . . ?
N1 C9 H9 125.5 . . ?
C11 C10 N2 106.7(4) . . ?
C11 C10 H10 126.7 . . ?
N2 C10 H10 126.7 . . ?
C10 C11 N1 108.5(3) . . ?
C10 C11 H11 125.7 . . ?
N1 C11 H11 125.7 . . ?
O1 C12 C14 111.8(3) . . ?
O1 C12 H12A 109.2 . . ?
C14 C12 H12A 109.2 . . ?
O1 C12 H12B 109.2 . . ?
C14 C12 H12B 109.2 . . ?
H12A C12 H12B 107.9 . . ?
C14 C13 S1 113.5(3) . . ?
C14 C13 Cl3 126.9(3) . . ?
S1 C13 Cl3 119.5(2) . . ?
C13 C14 C15 110.7(3) . . ?
C13 C14 C12 126.1(3) . . ?
C15 C14 C12 123.2(3) . . ?
C16 C15 C14 112.9(4) . . ?
C16 C15 H15 123.5 . . ?
C14 C15 H15 123.5 . . ?
C15 C16 S1 112.3(3) . . ?
C15 C16 H16 123.8 . . ?
S1 C16 H16 123.8 . . ?
O2 C17 O3 124.5(3) . . ?
O2 C17 C18 117.5(3) . . ?
O3 C17 C18 118.1(3) . . ?
C19 C18 C17 123.1(3) . . ?
C19 C18 H18 118.5 . . ?
C17 C18 H18 118.5 . . ?
C18 C19 C20 124.4(3) . . ?
C18 C19 H19 117.8 . . ?
C20 C19 H19 117.8 . . ?
O5 C20 O4 124.2(3) . . ?
O5 C20 C19 121.7(3) . . ?
O4 C20 C19 114.1(3) . . ?
C9 N1 C11 107.2(3) . . ?
C9 N1 C8 126.4(3) . . ?
C11 N1 C8 126.3(3) . . ?
C9 N2 C10 108.5(3) . . ?
C9 N2 H2N 122(3) . . ?
C10 N2 H2N 130(3) . . ?
C7 O1 C12 113.1(2) . . ?
C20 O4 H4 109.5 . . ?
C16 S1 C13 90.55(19) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 2.1(5) . . . . ?
C7 C1 C2 C3 -175.6(3) . . . . ?
C6 C1 C2 Cl1 -177.1(2) . . . . ?
C7 C1 C2 Cl1 5.2(4) . . . . ?
C1 C2 C3 C4 -0.9(5) . . . . ?
Cl1 C2 C3 C4 178.3(3) . . . . ?
C2 C3 C4 C5 -1.1(5) . . . . ?
C2 C3 C4 Cl2 179.7(2) . . . . ?
C3 C4 C5 C6 1.8(6) . . . . ?
Cl2 C4 C5 C6 -179.1(3) . . . . ?
C2 C1 C6 C5 -1.4(5) . . . . ?
C7 C1 C6 C5 176.3(3) . . . . ?
C4 C5 C6 C1 -0.5(6) . . . . ?
C6 C1 C7 O1 24.3(4) . . . . ?
C2 C1 C7 O1 -158.1(3) . . . . ?
C6 C1 C7 C8 -94.4(4) . . . . ?
C2 C1 C7 C8 83.2(4) . . . . ?
O1 C7 C8 N1 71.4(3) . . . . ?
C1 C7 C8 N1 -167.1(3) . . . . ?
N2 C10 C11 N1 0.7(4) . . . . ?
S1 C13 C14 C15 0.8(4) . . . . ?
Cl3 C13 C14 C15 -178.2(3) . . . . ?
S1 C13 C14 C12 -179.5(2) . . . . ?
Cl3 C13 C14 C12 1.4(5) . . . . ?
O1 C12 C14 C13 -110.5(4) . . . . ?
O1 C12 C14 C15 69.0(4) . . . . ?
C13 C14 C15 C16 -0.5(4) . . . . ?
C12 C14 C15 C16 179.8(3) . . . . ?
C14 C15 C16 S1 0.0(4) . . . . ?
O2 C17 C18 C19 -170.0(4) . . . . ?
O3 C17 C18 C19 9.3(6) . . . . ?
C17 C18 C19 C20 176.7(3) . . . . ?
C18 C19 C20 O5 177.4(4) . . . . ?
C18 C19 C20 O4 -2.0(6) . . . . ?
N2 C9 N1 C11 0.4(4) . . . . ?
N2 C9 N1 C8 176.7(3) . . . . ?
C10 C11 N1 C9 -0.7(4) . . . . ?
C10 C11 N1 C8 -177.0(3) . . . . ?
C7 C8 N1 C9 -100.4(4) . . . . ?
C7 C8 N1 C11 75.2(4) . . . . ?
N1 C9 N2 C10 0.0(4) . . . . ?
C11 C10 N2 C9 -0.4(4) . . . . ?
C8 C7 O1 C12 -144.8(3) . . . . ?
C1 C7 O1 C12 95.5(3) . . . . ?
C14 C12 O1 C7 73.9(3) . . . . ?
C15 C16 S1 C13 0.4(3) . . . . ?
C14 C13 S1 C16 -0.7(3) . . . . ?
Cl3 C13 S1 C16 178.4(2) . . . . ?

_refine_diff_density_max         0.701
_refine_diff_density_min         -0.532
_refine_diff_density_rms         0.122

####################################################################### 
# 
# 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_TCZ-PHOS_AM231023a
_database_code_depnum_ccdc_archive 'CCDC 2304002'
loop_
_audit_author_name
_audit_author_address
'Tejender Thakur'
;Central Drug Research Institute
India
;
_audit_update_record             
;
2023-10-27 deposited with the CCDC.	2023-11-14 downloaded from the CCDC.
;

_vrf_PLAT430_TCZ-PHOS_AM231023a  
;
PROBLEM: Short Inter D...A Contact  O3A      ..O4A      .       2.40 Ang.
RESPONSE: The observed short O...O contacts may be attributed to positional  disorder shown by the O-atoms of the phosphate anion.
;
_vrf_PLAT430_TCZ-PHOS_AM231023a_2 
;
PROBLEM: Short Inter D...A Contact  O3B      ..O4B      .       2.84 Ang.
RESPONSE: The observed short O...O contacts may be attributed to positional disorder shown by the O-atoms of the phosphate anion. 
;
# Added during the CSD deposition process: Friday 27 October 2023 04:25 AM
# end Validation Reply Form


_audit_creation_method           SHELXL-2019/2
_shelx_SHELXL_version_number     2019/2

_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H14 Cl3 N2 O S, O4 P'
_chemical_formula_sum            'C16 H14 Cl3 N2 O5 P S'
_chemical_formula_weight         483.67

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'
Cl Cl 0.3639 0.7018 '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'
P P 0.2955 0.4335 '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        'I 2/a'
_space_group_name_Hall           '-I 2ya'

_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, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z'
'-x+1/2, -y+1/2, -z+1/2'
'x, -y+1/2, z+1/2'

_cell_length_a                   17.2992(13)
_cell_length_b                   6.8054(5)
_cell_length_c                   34.882(3)
_cell_angle_alpha                90
_cell_angle_beta                 99.792(8)
_cell_angle_gamma                90
_cell_volume                     4046.7(6)
_cell_formula_units_Z            8
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    1692
_cell_measurement_theta_min      2.5610
_cell_measurement_theta_max      73.9490

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.588
_exptl_crystal_F_000             1968
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.440
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    6.105
_shelx_estimated_absorpt_T_min   0.174
_shelx_estimated_absorpt_T_max   0.888
_exptl_absorpt_correction_T_min  0.77916
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.88a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_type            HyPix
_diffrn_detector_area_resol_mean 10.0000
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0024557000
_diffrn_orient_matrix_UB_12      0.0472606000
_diffrn_orient_matrix_UB_13      0.0429566000
_diffrn_orient_matrix_UB_21      0.0879570000
_diffrn_orient_matrix_UB_22      -0.0491368000
_diffrn_orient_matrix_UB_23      0.0106418000
_diffrn_orient_matrix_UB_31      0.0204567000
_diffrn_orient_matrix_UB_32      0.2159809000
_diffrn_orient_matrix_UB_33      -0.0069790000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -17.00  24.00   0.50    0.05    --  -47.33  19.00   0.00   82
  2  ω   -121.00 -35.00   0.50    0.05    --  -47.33 -23.00  51.00  172
  3  ω   -137.00-112.00   0.50    0.05    --  -91.75 -23.00  51.00   50
  4  ω    -45.00 -20.00   0.50    0.05    --  -91.75  45.00 -30.00   50
  5  ω    -26.00  26.00   0.50    0.05    --  -47.33  23.00-143.00  104
  6  ω    151.00 176.00   0.50    0.05    --  113.25  45.00-120.00   50
  7  ω    101.00 172.00   0.50    0.05    --  113.25  23.00-143.00  142
  8  ω    103.00 128.00   0.50    0.05    --  113.25  45.00-120.00   50
  9  ω     62.00 103.00   0.50    0.05    --   47.33  23.00-143.00   82
 10  ω    103.00 137.00   0.50    0.05    --  113.25  45.00 -60.00   68
 11  ω    153.00 178.00   0.50    0.05    --  113.25  45.00 -60.00   50
 12  ω    101.00 165.00   0.50    0.05    --  113.25  45.00 -30.00  128
 13  ω    101.00 172.00   0.50    0.05    --  113.25  15.00  90.00  142
 14  ω    102.00 167.00   0.50    0.05    --  113.25  15.00 150.00  130
 15  ω     42.00 103.00   0.50    0.05    --  113.25 -77.00   0.00  122
 16  ω     47.00  73.00   0.50    0.05    --  113.25 -61.00  90.00   52
 17  ω     46.00  73.00   0.50    0.05    --  113.25 -61.00 150.00   54
 18  ω     43.00  73.00   0.50    0.05    --  113.25 -61.00  30.00   60
 19  ω     42.00  67.00   0.50    0.05    --  113.25 -61.00 -30.00   50
 20  ω     48.00  73.00   0.50    0.05    --  113.25 -61.00 -60.00   50
 21  ω     47.00  72.00   0.50    0.05    --  113.25 -61.00-120.00   50
 22  ω     48.00  73.00   0.50    0.05    --  113.25 -61.00-180.00   50
 23  ω     -7.00  20.00   0.50    0.05    --   47.33 -19.00 -60.00   54
 24  ω    -22.00   3.00   0.50    0.05    --   47.33 -23.00  51.00   50
 25  ω     61.00 105.00   0.50    0.05    --  113.25 -95.00 -60.00   88
 26  ω     44.00  96.00   0.50    0.05    --  113.25-125.00   0.00  104
 27  ω     59.00  99.00   0.50    0.05    --  113.25 -95.00   0.00   80
 28  ω     43.00  90.00   0.50    0.05    --   47.33-125.00-120.00   94
;
_diffrn_measurement_method       'ω scans'

_diffrn_reflns_number            14898
_diffrn_reflns_av_unetI/netI     0.0824
_diffrn_reflns_av_R_equivalents  0.0968
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -43
_diffrn_reflns_limit_l_max       44
_diffrn_reflns_theta_min         2.571
_diffrn_reflns_theta_max         80.796
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4311
_reflns_number_gt                2029
_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 1.171.42.88a (Rigaku OD, 2023)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.88a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.88a (Rigaku OD, 2023)'
_computing_structure_solution    'SHELXS-2013/1 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_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)+(0.1228P)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         4311
_refine_ls_number_parameters     260
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1453
_refine_ls_R_factor_gt           0.0748
_refine_ls_wR_factor_ref         0.2693
_refine_ls_wR_factor_gt          0.2161
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_restrained_S_all      1.096
_refine_ls_shift/su_max          0.003
_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
C1 C 0.4184(3) 0.1033(8) 0.41289(14) 0.0598(12) Uani 1 1 d . . . . .
C2 C 0.4535(3) 0.2432(9) 0.43897(18) 0.0720(15) Uani 1 1 d . . . . .
C3 C 0.5248(3) 0.2107(10) 0.46305(18) 0.0812(17) Uani 1 1 d . . . . .
H3 H 0.547722 0.307333 0.480153 0.097 Uiso 1 1 calc R U . . .
C4 C 0.5601(3) 0.0342(10) 0.46098(16) 0.0721(16) Uani 1 1 d . . . . .
C5 C 0.5281(3) -0.1095(10) 0.43550(18) 0.0858(18) Uani 1 1 d . . . . .
H5 H 0.553411 -0.229413 0.434295 0.103 Uiso 1 1 calc R U . . .
C6 C 0.4570(3) -0.0712(10) 0.41155(18) 0.0802(17) Uani 1 1 d . . . . .
H6 H 0.434931 -0.167190 0.394072 0.096 Uiso 1 1 calc R U . . .
C7 C 0.3418(3) 0.1419(8) 0.38521(15) 0.0622(13) Uani 1 1 d . . . . .
H7 H 0.312393 0.244786 0.396112 0.075 Uiso 1 1 calc R U . . .
C8 C 0.3608(3) 0.2105(9) 0.34650(16) 0.0714(15) Uani 1 1 d . . . . .
H8A H 0.395599 0.323129 0.350673 0.086 Uiso 1 1 calc R U . . .
H8B H 0.387732 0.106423 0.335079 0.086 Uiso 1 1 calc R U . . .
C9 C 0.2619(3) 0.4472(10) 0.31303(18) 0.0806(17) Uani 1 1 d . . . . .
H9 H 0.285892 0.560767 0.324131 0.097 Uiso 1 1 calc R U . . .
C10 C 0.1790(3) 0.2461(11) 0.27893(17) 0.0798(17) Uani 1 1 d . . . . .
H10 H 0.135058 0.198795 0.262405 0.096 Uiso 1 1 calc R U . . .
C11 C 0.2375(3) 0.1368(10) 0.29786(16) 0.0759(16) Uani 1 1 d . . . . .
H11 H 0.242515 0.000993 0.296633 0.091 Uiso 1 1 calc R U . . .
C12 C 0.2480(3) -0.0701(10) 0.40667(16) 0.0788(16) Uani 1 1 d . . . . .
H12A H 0.226328 0.050280 0.415334 0.095 Uiso 1 1 calc R U . . .
H12B H 0.279812 -0.132325 0.428943 0.095 Uiso 1 1 calc R U . . .
C13 C 0.1667(3) -0.3794(9) 0.40262(17) 0.0756(15) Uani 1 1 d . . . . .
C14 C 0.1832(3) -0.2048(8) 0.38918(15) 0.0643(13) Uani 1 1 d . . . . .
C15 C 0.1293(3) -0.1618(9) 0.35446(18) 0.0813(16) Uani 1 1 d . . . . .
H15 H 0.129842 -0.045075 0.340653 0.098 Uiso 1 1 calc R U . . .
C16 C 0.0780(3) -0.3065(11) 0.34384(18) 0.089(2) Uani 1 1 d . . . . .
H16 H 0.039911 -0.301461 0.321566 0.107 Uiso 1 1 calc R U . . .
Cl1B Cl 0.4119(3) 0.4724(6) 0.4410(3) 0.129(3) Uani 0.91(2) 1 d . . P . .
Cl1A Cl 0.3892(18) 0.428(5) 0.4552(5) 0.065(9) Uiso 0.09(2) 1 d . . P . .
Cl2 Cl 0.64963(9) -0.0113(3) 0.49090(5) 0.1021(7) Uani 1 1 d . . . . .
Cl3 Cl 0.20917(12) -0.4905(3) 0.44547(6) 0.1066(7) Uani 1 1 d . . . . .
S1 S 0.08879(10) -0.4979(3) 0.37451(5) 0.0904(6) Uani 1 1 d . . . . .
N1 N 0.2889(2) 0.2648(7) 0.31950(13) 0.0670(11) Uani 1 1 d . . . . .
N2 N 0.1947(3) 0.4394(11) 0.28798(16) 0.0903(17) Uani 1 1 d . . . . .
O1 O 0.29449(19) -0.0275(5) 0.37779(10) 0.0643(9) Uani 1 1 d . . . . .
O2 O 0.1322(3) 0.7625(8) 0.24657(17) 0.1228(19) Uani 1 1 d . . . . .
O3A O 0.0338(6) 0.5629(16) 0.2133(3) 0.102(3) Uiso 0.66(2) 1 d . . P . .
O3B O 0.0048(11) 0.628(3) 0.2068(5) 0.093(6) Uiso 0.34(2) 1 d . . P . .
O4A O 0.0036(5) 0.8853(15) 0.2334(2) 0.104(4) Uiso 0.66(2) 1 d . . P . .
O4B O 0.0336(15) 0.968(4) 0.2237(7) 0.148(9) Uiso 0.34(2) 1 d . . P . .
O5A O 0.0733(6) 0.8603(18) 0.1817(3) 0.104(3) Uiso 0.66(2) 1 d . . P . .
O5B O 0.0935(11) 0.782(3) 0.1787(5) 0.099(6) Uiso 0.34(2) 1 d . . P . .
P1 P 0.06527(8) 0.7857(2) 0.21841(5) 0.0703(5) Uani 1 1 d . . . . .
H2N H 0.167(5) 0.557(12) 0.279(2) 0.14(3) 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
C1 C6 1.367(8) . ?
C1 C2 1.384(7) . ?
C1 C7 1.523(6) . ?
C2 C3 1.386(7) . ?
C2 Cl1B 1.724(6) . ?
C2 Cl1A 1.83(2) . ?
C3 C4 1.355(8) . ?
C3 H3 0.9300 . ?
C4 C5 1.373(8) . ?
C4 Cl2 1.742(5) . ?
C5 C6 1.390(7) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 O1 1.413(6) . ?
C7 C8 1.516(7) . ?
C7 H7 0.9800 . ?
C8 N1 1.474(6) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 N1 1.332(7) . ?
C9 N2 1.331(7) . ?
C9 H9 0.9300 . ?
C10 C11 1.336(8) . ?
C10 N2 1.370(8) . ?
C10 H10 0.9300 . ?
C11 N1 1.375(7) . ?
C11 H11 0.9300 . ?
C12 O1 1.422(6) . ?
C12 C14 1.495(7) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.326(8) . ?
C13 Cl3 1.723(6) . ?
C13 S1 1.726(6) . ?
C14 C15 1.428(8) . ?
C15 C16 1.335(8) . ?
C15 H15 0.9300 . ?
C16 S1 1.676(7) . ?
C16 H16 0.9300 . ?
Cl1B Cl1A 0.75(2) . ?
N2 H2N 0.96(8) . ?
O2 P1 1.394(4) . ?
O3A O3B 0.679(17) . ?
O3A P1 1.611(9) . ?
O3B P1 1.504(15) . ?
O4A O4B 0.87(3) . ?
O4A P1 1.435(8) . ?
O4B P1 1.38(2) . ?
O5A O5B 0.654(19) . ?
O5A P1 1.405(9) . ?
O5B P1 1.546(18) . ?

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
C6 C1 C2 117.2(5) . . ?
C6 C1 C7 120.3(5) . . ?
C2 C1 C7 122.4(5) . . ?
C1 C2 C3 122.3(6) . . ?
C1 C2 Cl1B 120.6(4) . . ?
C3 C2 Cl1B 117.0(5) . . ?
C1 C2 Cl1A 117.0(12) . . ?
C3 C2 Cl1A 116.5(10) . . ?
Cl1B C2 Cl1A 24.0(7) . . ?
C4 C3 C2 118.1(5) . . ?
C4 C3 H3 120.9 . . ?
C2 C3 H3 120.9 . . ?
C3 C4 C5 122.0(5) . . ?
C3 C4 Cl2 119.2(5) . . ?
C5 C4 Cl2 118.7(5) . . ?
C4 C5 C6 118.3(6) . . ?
C4 C5 H5 120.9 . . ?
C6 C5 H5 120.9 . . ?
C1 C6 C5 122.0(6) . . ?
C1 C6 H6 119.0 . . ?
C5 C6 H6 119.0 . . ?
O1 C7 C8 107.1(4) . . ?
O1 C7 C1 113.0(4) . . ?
C8 C7 C1 108.7(4) . . ?
O1 C7 H7 109.3 . . ?
C8 C7 H7 109.3 . . ?
C1 C7 H7 109.3 . . ?
N1 C8 C7 111.1(4) . . ?
N1 C8 H8A 109.4 . . ?
C7 C8 H8A 109.4 . . ?
N1 C8 H8B 109.4 . . ?
C7 C8 H8B 109.4 . . ?
H8A C8 H8B 108.0 . . ?
N1 C9 N2 108.4(6) . . ?
N1 C9 H9 125.8 . . ?
N2 C9 H9 125.8 . . ?
C11 C10 N2 108.5(5) . . ?
C11 C10 H10 125.8 . . ?
N2 C10 H10 125.8 . . ?
C10 C11 N1 106.5(6) . . ?
C10 C11 H11 126.8 . . ?
N1 C11 H11 126.8 . . ?
O1 C12 C14 108.1(4) . . ?
O1 C12 H12A 110.1 . . ?
C14 C12 H12A 110.1 . . ?
O1 C12 H12B 110.1 . . ?
C14 C12 H12B 110.1 . . ?
H12A C12 H12B 108.4 . . ?
C14 C13 Cl3 127.9(5) . . ?
C14 C13 S1 114.3(5) . . ?
Cl3 C13 S1 117.7(4) . . ?
C13 C14 C15 109.6(5) . . ?
C13 C14 C12 126.6(5) . . ?
C15 C14 C12 123.8(5) . . ?
C16 C15 C14 113.1(6) . . ?
C16 C15 H15 123.5 . . ?
C14 C15 H15 123.5 . . ?
C15 C16 S1 113.6(5) . . ?
C15 C16 H16 123.2 . . ?
S1 C16 H16 123.2 . . ?
Cl1A Cl1B C2 86.2(18) . . ?
Cl1B Cl1A C2 69.8(16) . . ?
C16 S1 C13 89.5(3) . . ?
C9 N1 C11 108.8(5) . . ?
C9 N1 C8 125.1(5) . . ?
C11 N1 C8 126.1(5) . . ?
C9 N2 C10 107.8(6) . . ?
C9 N2 H2N 121(5) . . ?
C10 N2 H2N 132(5) . . ?
C7 O1 C12 114.6(4) . . ?
O3B O3A P1 68.8(16) . . ?
O3A O3B P1 86.4(18) . . ?
O4B O4A P1 68.8(17) . . ?
O4A O4B P1 75(2) . . ?
O5B O5A P1 90(2) . . ?
O5A O5B P1 65.3(19) . . ?
O4B P1 O2 107.9(9) . . ?
O4B P1 O5A 84.3(11) . . ?
O2 P1 O5A 118.9(4) . . ?
O4B P1 O4A 36.0(11) . . ?
O2 P1 O4A 112.1(4) . . ?
O5A P1 O4A 110.8(5) . . ?
O4B P1 O3B 113.8(11) . . ?
O2 P1 O3B 124.4(9) . . ?
O5A P1 O3B 100.7(8) . . ?
O4A P1 O3B 84.8(7) . . ?
O4B P1 O5B 109.0(12) . . ?
O2 P1 O5B 106.2(7) . . ?
O5A P1 O5B 25.0(7) . . ?
O4A P1 O5B 134.5(8) . . ?
O3B P1 O5B 93.5(8) . . ?
O4B P1 O3A 136.6(12) . . ?
O2 P1 O3A 101.3(5) . . ?
O5A P1 O3A 108.9(6) . . ?
O4A P1 O3A 103.1(5) . . ?
O3B P1 O3A 24.9(7) . . ?
O5B P1 O3A 92.3(8) . . ?

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
C6 C1 C2 C3 -0.1(9) . . . . ?
C7 C1 C2 C3 -177.4(5) . . . . ?
C6 C1 C2 Cl1B 176.6(7) . . . . ?
C7 C1 C2 Cl1B -0.6(9) . . . . ?
C6 C1 C2 Cl1A -156.3(11) . . . . ?
C7 C1 C2 Cl1A 26.5(12) . . . . ?
C1 C2 C3 C4 -0.8(9) . . . . ?
Cl1B C2 C3 C4 -177.7(7) . . . . ?
Cl1A C2 C3 C4 155.5(13) . . . . ?
C2 C3 C4 C5 1.2(9) . . . . ?
C2 C3 C4 Cl2 -179.9(4) . . . . ?
C3 C4 C5 C6 -0.6(10) . . . . ?
Cl2 C4 C5 C6 -179.5(5) . . . . ?
C2 C1 C6 C5 0.7(9) . . . . ?
C7 C1 C6 C5 178.0(6) . . . . ?
C4 C5 C6 C1 -0.4(10) . . . . ?
C6 C1 C7 O1 36.2(7) . . . . ?
C2 C1 C7 O1 -146.6(5) . . . . ?
C6 C1 C7 C8 -82.6(6) . . . . ?
C2 C1 C7 C8 94.6(6) . . . . ?
O1 C7 C8 N1 62.0(6) . . . . ?
C1 C7 C8 N1 -175.6(4) . . . . ?
N2 C10 C11 N1 1.4(7) . . . . ?
Cl3 C13 C14 C15 -174.5(5) . . . . ?
S1 C13 C14 C15 0.9(6) . . . . ?
Cl3 C13 C14 C12 5.8(9) . . . . ?
S1 C13 C14 C12 -178.8(5) . . . . ?
O1 C12 C14 C13 124.2(6) . . . . ?
O1 C12 C14 C15 -55.4(8) . . . . ?
C13 C14 C15 C16 -1.4(8) . . . . ?
C12 C14 C15 C16 178.2(5) . . . . ?
C14 C15 C16 S1 1.4(7) . . . . ?
C1 C2 Cl1B Cl1A 88(3) . . . . ?
C3 C2 Cl1B Cl1A -95(2) . . . . ?
C1 C2 Cl1A Cl1B -105(3) . . . . ?
C3 C2 Cl1A Cl1B 97(2) . . . . ?
C15 C16 S1 C13 -0.7(5) . . . . ?
C14 C13 S1 C16 -0.1(5) . . . . ?
Cl3 C13 S1 C16 175.8(4) . . . . ?
N2 C9 N1 C11 0.2(7) . . . . ?
N2 C9 N1 C8 -178.0(5) . . . . ?
C10 C11 N1 C9 -1.0(6) . . . . ?
C10 C11 N1 C8 177.2(5) . . . . ?
C7 C8 N1 C9 98.2(6) . . . . ?
C7 C8 N1 C11 -79.7(7) . . . . ?
N1 C9 N2 C10 0.7(7) . . . . ?
C11 C10 N2 C9 -1.3(7) . . . . ?
C8 C7 O1 C12 -157.9(4) . . . . ?
C1 C7 O1 C12 82.4(5) . . . . ?
C14 C12 O1 C7 161.0(4) . . . . ?
O4A O4B P1 O2 -103.3(15) . . . . ?
O4A O4B P1 O5A 138.2(16) . . . . ?
O4A O4B P1 O3B 39(2) . . . . ?
O4A O4B P1 O5B 141.9(15) . . . . ?
O4A O4B P1 O3A 27(3) . . . . ?
O5B O5A P1 O4B 172(2) . . . . ?
O5B O5A P1 O2 64.5(19) . . . . ?
O5B O5A P1 O4A -163.4(18) . . . . ?
O5B O5A P1 O3B -75(2) . . . . ?
O5B O5A P1 O3A -50.7(19) . . . . ?
O4B O4A P1 O2 90.2(17) . . . . ?
O4B O4A P1 O5A -45.2(18) . . . . ?
O4B O4A P1 O3B -144.6(19) . . . . ?
O4B O4A P1 O5B -55(2) . . . . ?
O4B O4A P1 O3A -161.5(17) . . . . ?
O3A O3B P1 O4B -160(2) . . . . ?
O3A O3B P1 O2 -24(2) . . . . ?
O3A O3B P1 O5A 112.1(17) . . . . ?
O3A O3B P1 O4A -137.7(18) . . . . ?
O3A O3B P1 O5B 87.9(19) . . . . ?
O5A O5B P1 O4B -9(2) . . . . ?
O5A O5B P1 O2 -124.6(17) . . . . ?
O5A O5B P1 O4A 22(2) . . . . ?
O5A O5B P1 O3B 108(2) . . . . ?
O5A O5B P1 O3A 132.9(18) . . . . ?
O3B O3A P1 O4B 28(3) . . . . ?
O3B O3A P1 O2 159.7(17) . . . . ?
O3B O3A P1 O5A -74.2(18) . . . . ?
O3B O3A P1 O4A 43.5(18) . . . . ?
O3B O3A P1 O5B -93.3(19) . . . . ?

_refine_diff_density_max         0.511
_refine_diff_density_min         -0.420
_refine_diff_density_rms         0.071

####################################################################### 
# 
# 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_TCA-TPTH1
_database_code_depnum_ccdc_archive 'CCDC 2285616'
loop_
_audit_author_name
_audit_author_address
'Tejender Thakur'
;CSIR Central Drug Research Institute
India
;
_audit_update_record             
;
2023-07-31 deposited with the CCDC.	2023-11-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            'Tioconazole-Terepthalic acid cocrystal'
_chemical_melting_point          ?
_chemical_formula_moiety         
'C16 H11 Cl3 N2 O S, C16 H13 Cl3 N2 O S, C8 H6 O4'
_chemical_formula_sum            'C40 H30 Cl6 N4 O6 S2'
_chemical_formula_weight         939.50

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'
Cl Cl 0.3639 0.7018 '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                   10.7290(3)
_cell_length_b                   12.8274(3)
_cell_length_c                   16.0617(5)
_cell_angle_alpha                78.507(2)
_cell_angle_beta                 83.668(2)
_cell_angle_gamma                85.091(2)
_cell_volume                     2148.36(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    14208
_cell_measurement_theta_min      2.7680
_cell_measurement_theta_max      72.0590

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.452
_exptl_crystal_F_000             960
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.380
_exptl_crystal_size_mid          0.340
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    4.982
_shelx_estimated_absorpt_T_min   0.253
_shelx_estimated_absorpt_T_max   0.610
_exptl_absorpt_correction_T_min  0.23093
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_source_power             0.0
_diffrn_source_voltage           50.0
_diffrn_source_current           0.6
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   MicroMax003_Cu
_diffrn_radiation_monochromator  Confocal
_diffrn_measurement_specimen_support Loop
_diffrn_detector                 CCD
_diffrn_measurement_device       
;
AFC12 (Right): Kappa 3 circle
;
_diffrn_measurement_device_type  
;
Rigaku Saturn724+ (4x4 bin mode)
;
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_details      
;
scan:
	Number of images: 120
	           Slice: -130.0000 - -10.0000
	     Image width: 1.0000
	        Exp time: 4.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: -72.0000
	             Phi: 0.0000
	             XTD: 35.0004
	          2theta: -39.6388
scan:
	Number of images: 120
	           Slice: -130.0000 - -10.0000
	     Image width: 1.0000
	        Exp time: 4.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: -72.0000
	             Phi: 70.0000
	             XTD: 35.0004
	          2theta: -39.6388
scan:
	Number of images: 120
	           Slice: -130.0000 - -10.0000
	     Image width: 1.0000
	        Exp time: 4.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: -72.0000
	             Phi: 140.0000
	             XTD: 35.0004
	          2theta: -39.6388
scan:
	Number of images: 120
	           Slice: -130.0000 - -10.0000
	     Image width: 1.0000
	        Exp time: 4.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: -72.0000
	             Phi: 210.0000
	             XTD: 35.0004
	          2theta: -39.6388
scan:
	Number of images: 120
	           Slice: -130.0000 - -10.0000
	     Image width: 1.0000
	        Exp time: 4.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: -72.0000
	             Phi: 280.0000
	             XTD: 35.0004
	          2theta: -39.6388
scan:
	Number of images: 180
	           Slice: -130.0000 - 50.0000
	     Image width: 1.0000
	        Exp time: 4.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 0.0000
	             Phi: 0.0000
	             XTD: 35.0004
	          2theta: -39.6388
scan:
	Number of images: 120
	           Slice: -100.0000 - 20.0000
	     Image width: 1.0000
	        Exp time: 4.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 72.0000
	             Phi: 0.0000
	             XTD: 35.0004
	          2theta: -69.6388
scan:
	Number of images: 120
	           Slice: -100.0000 - 20.0000
	     Image width: 1.0000
	        Exp time: 4.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 72.0000
	             Phi: 70.0000
	             XTD: 35.0004
	          2theta: -69.6388
scan:
	Number of images: 120
	           Slice: -100.0000 - 20.0000
	     Image width: 1.0000
	        Exp time: 4.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 72.0000
	             Phi: 140.0000
	             XTD: 35.0004
	          2theta: -69.6388
scan:
	Number of images: 120
	           Slice: -100.0000 - 20.0000
	     Image width: 1.0000
	        Exp time: 4.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 72.0000
	             Phi: 210.0000
	             XTD: 35.0004
	          2theta: -69.6388
scan:
	Number of images: 120
	           Slice: -100.0000 - 20.0000
	     Image width: 1.0000
	        Exp time: 4.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 72.0000
	             Phi: 280.0000
	             XTD: 35.0004
	          2theta: -69.6388
scan:
	Number of images: 180
	           Slice: -160.0000 - 20.0000
	     Image width: 1.0000
	        Exp time: 4.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 0.0000
	             Phi: 0.0000
	             XTD: 35.0004
	          2theta: -69.6388
scan:
	Number of images: 120
	           Slice: -190.0000 - -70.0000
	     Image width: 1.0000
	        Exp time: 4.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: -72.0000
	             Phi: 0.0000
	             XTD: 35.0004
	          2theta: -99.6388
scan:
	Number of images: 120
	           Slice: -190.0000 - -70.0000
	     Image width: 1.0000
	        Exp time: 4.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: -72.0000
	             Phi: 70.0000
	             XTD: 35.0004
	          2theta: -99.6388
scan:
	Number of images: 120
	           Slice: -190.0000 - -70.0000
	     Image width: 1.0000
	        Exp time: 4.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: -72.0000
	             Phi: 140.0000
	             XTD: 35.0004
	          2theta: -99.6388
scan:
	Number of images: 120
	           Slice: -190.0000 - -70.0000
	     Image width: 1.0000
	        Exp time: 4.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: -72.0000
	             Phi: 210.0000
	             XTD: 35.0004
	          2theta: -99.6388
scan:
	Number of images: 120
	           Slice: -190.0000 - -70.0000
	     Image width: 1.0000
	        Exp time: 4.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: -72.0000
	             Phi: 280.0000
	             XTD: 35.0004
	          2theta: -99.6388
scan:
	Number of images: 120
	           Slice: -130.0000 - -10.0000
	     Image width: 1.0000
	        Exp time: 4.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 72.0000
	             Phi: 0.0000
	             XTD: 35.0004
	          2theta: -99.6388
scan:
	Number of images: 120
	           Slice: -130.0000 - -10.0000
	     Image width: 1.0000
	        Exp time: 4.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 72.0000
	             Phi: 70.0000
	             XTD: 35.0004
	          2theta: -99.6388
scan:
	Number of images: 120
	           Slice: -130.0000 - -10.0000
	     Image width: 1.0000
	        Exp time: 4.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 72.0000
	             Phi: 140.0000
	             XTD: 35.0004
	          2theta: -99.6388
scan:
	Number of images: 120
	           Slice: -130.0000 - -10.0000
	     Image width: 1.0000
	        Exp time: 4.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 72.0000
	             Phi: 210.0000
	             XTD: 35.0004
	          2theta: -99.6388
scan:
	Number of images: 120
	           Slice: -130.0000 - -10.0000
	     Image width: 1.0000
	        Exp time: 4.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 72.0000
	             Phi: 280.0000
	             XTD: 35.0004
	          2theta: -99.6388
scan:
	Number of images: 180
	           Slice: -190.0000 - -10.0000
	     Image width: 1.0000
	        Exp time: 4.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 0.0000
	             Phi: 0.0000
	             XTD: 35.0004
	          2theta: -99.6388

;
_diffrn_reflns_number            45274
_diffrn_reflns_av_unetI/netI     0.0717
_diffrn_reflns_av_R_equivalents  0.1375
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.820
_diffrn_reflns_theta_max         72.864
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.959
_diffrn_measured_fraction_theta_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.959
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.959
_diffrn_reflns_point_group_measured_fraction_full 0.982
_reflns_number_total             8208
_reflns_number_gt                5232
_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_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_structure_solution    'SHELXS-2013/1 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'
_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)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   direct
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.0065(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         8208
_refine_ls_number_parameters     543
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1246
_refine_ls_R_factor_gt           0.0958
_refine_ls_wR_factor_ref         0.3330
_refine_ls_wR_factor_gt          0.2802
_refine_ls_goodness_of_fit_ref   1.187
_refine_ls_restrained_S_all      1.187
_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
C15A C -0.1401(17) 0.9229(11) 0.3667(10) 0.115(4) Uiso 0.50(2) 1 d . . P A 2
C16A C -0.0687(19) 0.9384(12) 0.4142(10) 0.134(5) Uiso 0.50(2) 1 d . . P A 2
S1A S 0.0196(13) 0.8248(16) 0.4805(8) 0.167(5) Uani 0.50(2) 1 d . . P A 2
Cl3B Cl -0.0406(14) 0.6225(5) 0.4929(6) 0.171(4) Uani 0.50(2) 1 d . . P A 2
C15B C -0.2044(16) 0.9064(10) 0.3834(8) 0.111(4) Uiso 0.50(2) 1 d . . P A 1
C16B C -0.1458(19) 0.9520(11) 0.4134(10) 0.127(5) Uiso 0.50(2) 1 d . . P A 1
S1B S -0.0142(12) 0.8641(9) 0.4753(8) 0.135(3) Uani 0.50(2) 1 d . . P A 1
Cl3A Cl 0.0030(16) 0.6382(12) 0.4820(10) 0.242(6) Uani 0.50(2) 1 d . . P A 1
C1 C -0.1051(4) 0.5655(3) 0.2541(2) 0.0738(9) Uani 1 1 d . . . . .
C2 C 0.0027(4) 0.5010(3) 0.2683(3) 0.0850(11) Uani 1 1 d . . . . .
C3 C 0.0062(6) 0.3903(4) 0.2749(3) 0.1019(14) Uani 1 1 d . . . . .
H3 H 0.081070 0.348868 0.282577 0.122 Uiso 1 1 calc R U . . .
C4 C -0.0988(7) 0.3457(4) 0.2701(3) 0.1059(15) Uani 1 1 d . . . . .
C5 C -0.2115(6) 0.4066(5) 0.2556(4) 0.1132(16) Uani 1 1 d . . . . .
H5 H -0.284164 0.374120 0.251373 0.136 Uiso 1 1 calc R U . . .
C6 C -0.2130(5) 0.5155(4) 0.2476(3) 0.1009(13) Uani 1 1 d . . . . .
H6 H -0.287474 0.556643 0.237738 0.121 Uiso 1 1 calc R U . . .
C7 C -0.1061(3) 0.6854(3) 0.2446(2) 0.0721(9) Uani 1 1 d . . . . .
H7 H -0.039848 0.703086 0.275841 0.086 Uiso 1 1 calc R U . . .
C8 C -0.0827(4) 0.7365(3) 0.1505(2) 0.0768(9) Uani 1 1 d . . . . .
H8A H -0.018045 0.693699 0.123026 0.092 Uiso 1 1 calc R U . . .
H8B H -0.159054 0.737732 0.122992 0.092 Uiso 1 1 calc R U . . .
C9 C -0.1098(4) 0.9358(3) 0.1121(3) 0.0772(10) Uani 1 1 d . . . . .
H9 H -0.190675 0.939167 0.095584 0.093 Uiso 1 1 calc R U . . .
C10 C 0.0634(4) 0.9805(4) 0.1393(3) 0.0975(13) Uani 1 1 d . . . . .
H10 H 0.127611 1.021656 0.145937 0.117 Uiso 1 1 calc R U . . .
C11 C 0.0680(4) 0.8746(4) 0.1564(4) 0.1060(16) Uani 1 1 d . . . . .
H11 H 0.135341 0.829467 0.176264 0.127 Uiso 1 1 calc R U . . .
C12 C -0.2432(4) 0.7144(4) 0.3660(3) 0.0929(12) Uani 1 1 d . . . . .
H12A H -0.225016 0.639577 0.389593 0.111 Uiso 1 1 calc R U . . .
H12B H -0.330524 0.732699 0.383228 0.111 Uiso 1 1 calc R U . . .
C13 C -0.0710(6) 0.7555(6) 0.4480(4) 0.129(2) Uani 1 1 d . . . . .
C14 C -0.1607(5) 0.7806(5) 0.4008(3) 0.1118(16) Uani 1 1 d . . . . .
C17 C 0.3987(4) 0.0707(3) 0.2638(2) 0.0759(9) Uani 1 1 d . . . . .
C18 C 0.5037(4) 0.0061(3) 0.2444(3) 0.0787(10) Uani 1 1 d . . . . .
C19 C 0.5032(5) -0.1033(3) 0.2541(3) 0.0910(12) Uani 1 1 d . . . . .
H19 H 0.575505 -0.144127 0.240165 0.109 Uiso 1 1 calc R U . . .
C20 C 0.3952(6) -0.1490(4) 0.2844(3) 0.1001(13) Uani 1 1 d . . . . .
C21 C 0.2864(6) -0.0893(5) 0.3037(3) 0.1138(17) Uani 1 1 d . . . . .
H21 H 0.212071 -0.122298 0.323670 0.137 Uiso 1 1 calc R U . . .
C22 C 0.2894(4) 0.0211(4) 0.2929(3) 0.1007(13) Uani 1 1 d . . . . .
H22 H 0.216345 0.061689 0.305669 0.121 Uiso 1 1 calc R U . . .
Cl6 Cl 0.5690(3) 0.12082(19) 0.48389(19) 0.2215(13) Uani 1 1 d . . . . .
C24 C 0.3945(4) 0.2424(3) 0.1585(2) 0.0775(9) Uani 1 1 d . . . . .
H24A H 0.442378 0.197804 0.122539 0.093 Uiso 1 1 calc R U . . .
H24B H 0.307247 0.246135 0.146935 0.093 Uiso 1 1 calc R U . . .
C27 C 0.5604(4) 0.3722(3) 0.1100(3) 0.0888(11) Uani 1 1 d . . . . .
H27 H 0.627641 0.324644 0.098731 0.107 Uiso 1 1 calc R U . . .
N4 N 0.4460(3) 0.5220(3) 0.1229(2) 0.0857(9) Uani 1 1 d . . . . .
C25 C 0.3763(4) 0.4409(3) 0.1426(3) 0.0878(11) Uani 1 1 d . . . . .
H25 H 0.290597 0.447138 0.159234 0.105 Uiso 1 1 calc R U . . .
C28 C 0.3234(6) 0.2219(5) 0.3881(3) 0.1171(17) Uani 1 1 d . . . . .
H28A H 0.344677 0.146724 0.408164 0.140 Uiso 1 1 calc R U . . .
H28B H 0.244809 0.240886 0.419166 0.140 Uiso 1 1 calc R U . . .
C29 C 0.5257(8) 0.2478(5) 0.4467(4) 0.132(2) Uani 1 1 d . . . . .
C30 C 0.4251(6) 0.2860(4) 0.4064(3) 0.1088(16) Uani 1 1 d . . . . .
C31 C 0.4230(8) 0.4043(6) 0.3839(5) 0.143(2) Uani 1 1 d . . . . .
H31 H 0.360099 0.446600 0.355456 0.172 Uiso 1 1 calc R U . . .
C32 C 0.5168(11) 0.4417(6) 0.4078(6) 0.176(3) Uani 1 1 d . . . . .
H32 H 0.529357 0.514105 0.398109 0.212 Uiso 1 1 calc R U . . .
C33 C 0.0047(3) 0.3900(3) 0.0286(2) 0.0666(8) Uani 1 1 d . . . . .
C34 C -0.1077(3) 0.4464(3) 0.0114(3) 0.0838(11) Uani 1 1 d . . . . .
H34 H -0.181247 0.410785 0.018888 0.101 Uiso 1 1 calc R U . . .
C35 C 0.1119(4) 0.4456(3) 0.0165(3) 0.0866(11) Uani 1 1 d . . . . .
H35 H 0.188687 0.408841 0.027501 0.104 Uiso 1 1 calc R U . . .
C36 C 0.0155(3) 0.2727(3) 0.0600(2) 0.0753(9) Uani 1 1 d . . . . .
C37 C 0.5070(3) 0.8906(3) 0.0309(2) 0.0715(9) Uani 1 1 d . . . . .
C38 C 0.3928(4) 0.9506(3) 0.0388(3) 0.0784(10) Uani 1 1 d . . . . .
H38 H 0.320964 0.917279 0.064790 0.094 Uiso 1 1 calc R U . . .
C39 C 0.6136(4) 0.9413(3) -0.0082(3) 0.0770(9) Uani 1 1 d . . . . .
H39 H 0.689845 0.901737 -0.013724 0.092 Uiso 1 1 calc R U . . .
C40 C 0.5183(4) 0.7734(3) 0.0643(3) 0.0819(10) Uani 1 1 d . . . . .
N1 N -0.0438(3) 0.8442(2) 0.1395(2) 0.0728(8) Uani 1 1 d . . . . .
N2 N -0.0489(3) 1.0196(3) 0.1109(2) 0.0786(8) Uani 1 1 d . . . . .
N3 N 0.4394(3) 0.3476(2) 0.13692(19) 0.0734(8) Uani 1 1 d . . . . .
C26 C 0.5640(4) 0.4786(3) 0.1028(3) 0.0910(12) Uani 1 1 d . . . . .
H26 H 0.635569 0.516631 0.086723 0.109 Uiso 1 1 calc R U . . .
O1 O -0.2237(2) 0.7313(2) 0.27468(16) 0.0833(7) Uani 1 1 d . . . . .
O2 O 0.3074(3) 0.2397(2) 0.29931(19) 0.0963(9) Uani 1 1 d . . . . .
O3 O -0.0876(2) 0.2257(2) 0.0588(2) 0.0866(8) Uani 1 1 d . . . . .
H3A H -0.072287 0.160954 0.066950 0.130 Uiso 1 1 calc R U . . .
O4 O 0.1119(3) 0.2258(2) 0.0828(3) 0.1035(10) Uani 1 1 d . . . . .
O5 O 0.4101(3) 0.7298(2) 0.0830(2) 0.0958(9) Uani 1 1 d . . . . .
H5A H 0.422313 0.665245 0.099121 0.144 Uiso 1 1 calc R U . . .
O6 O 0.6194(3) 0.7248(2) 0.0714(2) 0.1060(10) Uani 1 1 d . . . . .
S2 S 0.6188(2) 0.3440(2) 0.46005(12) 0.1634(8) Uani 1 1 d . . . . .
Cl1 Cl 0.14102(11) 0.55775(11) 0.27326(13) 0.1327(7) Uani 1 1 d . . . . .
Cl2 Cl -0.0978(2) 0.20729(10) 0.28263(10) 0.1502(8) Uani 1 1 d . . . . .
Cl4 Cl 0.64462(10) 0.06357(9) 0.20600(9) 0.1053(5) Uani 1 1 d . . . . .
Cl5 Cl 0.3912(2) -0.28698(11) 0.29838(11) 0.1476(7) Uani 1 1 d . . . . .
C23 C 0.4050(3) 0.1916(3) 0.2508(2) 0.0738(9) Uani 1 1 d . . . . .
H23 H 0.485891 0.207115 0.267089 0.089 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
C15A C16A 1.19(2) . ?
C15A C14 1.824(15) . ?
C16A S1A 1.88(2) . ?
S1A C13 1.566(15) . ?
Cl3B C13 1.734(9) . ?
C15B C16B 1.101(18) . ?
C15B C14 1.620(13) . ?
C16B S1B 1.960(19) . ?
S1B C13 1.717(13) . ?
Cl3A C13 1.661(13) . ?
C1 C2 1.375(6) . ?
C1 C6 1.393(6) . ?
C1 C7 1.515(5) . ?
C2 C3 1.401(6) . ?
C2 Cl1 1.724(5) . ?
C3 C4 1.323(8) . ?
C3 H3 0.9300 . ?
C4 C5 1.398(8) . ?
C4 Cl2 1.745(5) . ?
C5 C6 1.376(7) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 O1 1.422(4) . ?
C7 C8 1.525(5) . ?
C7 H7 0.9800 . ?
C8 N1 1.449(5) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 N2 1.300(5) . ?
C9 N1 1.340(5) . ?
C9 H9 0.9300 . ?
C10 C11 1.328(6) . ?
C10 N2 1.356(5) . ?
C10 H10 0.9300 . ?
C11 N1 1.364(5) . ?
C11 H11 0.9300 . ?
C12 O1 1.434(5) . ?
C12 C14 1.497(8) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.271(8) . ?
C17 C22 1.373(6) . ?
C17 C18 1.385(5) . ?
C17 C23 1.529(6) . ?
C18 C19 1.382(6) . ?
C18 Cl4 1.736(4) . ?
C19 C20 1.342(7) . ?
C19 H19 0.9300 . ?
C20 C21 1.381(8) . ?
C20 Cl5 1.743(5) . ?
C21 C22 1.395(7) . ?
C21 H21 0.9300 . ?
C22 H22 0.9300 . ?
Cl6 C29 1.665(7) . ?
C24 N3 1.435(5) . ?
C24 C23 1.508(5) . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C27 C26 1.350(6) . ?
C27 N3 1.366(5) . ?
C27 H27 0.9300 . ?
N4 C25 1.301(6) . ?
N4 C26 1.370(5) . ?
C25 N3 1.338(5) . ?
C25 H25 0.9300 . ?
C28 O2 1.425(6) . ?
C28 C30 1.507(9) . ?
C28 H28A 0.9700 . ?
C28 H28B 0.9700 . ?
C29 C30 1.327(9) . ?
C29 S2 1.711(8) . ?
C30 C31 1.488(9) . ?
C31 C32 1.277(11) . ?
C31 H31 0.9300 . ?
C32 S2 1.739(10) . ?
C32 H32 0.9300 . ?
C33 C34 1.378(5) . ?
C33 C35 1.381(6) . ?
C33 C36 1.487(5) . ?
C34 C35 1.366(5) 2_565 ?
C34 H34 0.9300 . ?
C35 H35 0.9300 . ?
C36 O4 1.207(4) . ?
C36 O3 1.308(5) . ?
C37 C39 1.390(6) . ?
C37 C38 1.398(5) . ?
C37 C40 1.491(5) . ?
C38 C39 1.375(5) 2_675 ?
C38 H38 0.9300 . ?
C39 H39 0.9300 . ?
C40 O6 1.209(5) . ?
C40 O5 1.311(5) . ?
C26 H26 0.9300 . ?
O2 C23 1.409(4) . ?
O3 H3A 0.8200 . ?
O5 H5A 0.8200 . ?
C23 H23 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
C16A C15A C14 102.4(11) . . ?
C15A C16A S1A 121.2(13) . . ?
C13 S1A C16A 83.4(8) . . ?
C16B C15B C14 111.5(12) . . ?
C15B C16B S1B 113.8(12) . . ?
C13 S1B C16B 87.5(7) . . ?
C2 C1 C6 116.9(4) . . ?
C2 C1 C7 121.6(4) . . ?
C6 C1 C7 121.5(4) . . ?
C1 C2 C3 122.4(4) . . ?
C1 C2 Cl1 119.5(3) . . ?
C3 C2 Cl1 118.1(4) . . ?
C4 C3 C2 118.8(5) . . ?
C4 C3 H3 120.6 . . ?
C2 C3 H3 120.6 . . ?
C3 C4 C5 121.6(5) . . ?
C3 C4 Cl2 119.5(5) . . ?
C5 C4 Cl2 118.8(5) . . ?
C6 C5 C4 118.8(5) . . ?
C6 C5 H5 120.6 . . ?
C4 C5 H5 120.6 . . ?
C5 C6 C1 121.3(5) . . ?
C5 C6 H6 119.3 . . ?
C1 C6 H6 119.3 . . ?
O1 C7 C1 112.6(3) . . ?
O1 C7 C8 106.4(3) . . ?
C1 C7 C8 109.8(3) . . ?
O1 C7 H7 109.3 . . ?
C1 C7 H7 109.3 . . ?
C8 C7 H7 109.3 . . ?
N1 C8 C7 111.7(3) . . ?
N1 C8 H8A 109.3 . . ?
C7 C8 H8A 109.3 . . ?
N1 C8 H8B 109.3 . . ?
C7 C8 H8B 109.3 . . ?
H8A C8 H8B 107.9 . . ?
N2 C9 N1 113.0(4) . . ?
N2 C9 H9 123.5 . . ?
N1 C9 H9 123.5 . . ?
C11 C10 N2 109.8(4) . . ?
C11 C10 H10 125.1 . . ?
N2 C10 H10 125.1 . . ?
C10 C11 N1 107.6(4) . . ?
C10 C11 H11 126.2 . . ?
N1 C11 H11 126.2 . . ?
O1 C12 C14 111.1(4) . . ?
O1 C12 H12A 109.4 . . ?
C14 C12 H12A 109.4 . . ?
O1 C12 H12B 109.4 . . ?
C14 C12 H12B 109.4 . . ?
H12A C12 H12B 108.0 . . ?
C14 C13 S1A 132.0(9) . . ?
C14 C13 Cl3A 130.7(8) . . ?
C14 C13 S1B 112.9(7) . . ?
Cl3A C13 S1B 116.3(7) . . ?
C14 C13 Cl3B 118.7(7) . . ?
S1A C13 Cl3B 109.2(7) . . ?
C13 C14 C12 132.0(6) . . ?
C13 C14 C15B 114.2(7) . . ?
C12 C14 C15B 113.4(7) . . ?
C13 C14 C15A 99.2(7) . . ?
C12 C14 C15A 127.6(6) . . ?
C22 C17 C18 116.8(4) . . ?
C22 C17 C23 122.3(4) . . ?
C18 C17 C23 120.9(3) . . ?
C19 C18 C17 123.4(4) . . ?
C19 C18 Cl4 117.3(3) . . ?
C17 C18 Cl4 119.3(3) . . ?
C20 C19 C18 118.0(4) . . ?
C20 C19 H19 121.0 . . ?
C18 C19 H19 121.0 . . ?
C19 C20 C21 121.7(5) . . ?
C19 C20 Cl5 119.3(5) . . ?
C21 C20 Cl5 119.0(4) . . ?
C20 C21 C22 119.2(4) . . ?
C20 C21 H21 120.4 . . ?
C22 C21 H21 120.4 . . ?
C17 C22 C21 121.0(5) . . ?
C17 C22 H22 119.5 . . ?
C21 C22 H22 119.5 . . ?
N3 C24 C23 112.7(3) . . ?
N3 C24 H24A 109.1 . . ?
C23 C24 H24A 109.1 . . ?
N3 C24 H24B 109.1 . . ?
C23 C24 H24B 109.1 . . ?
H24A C24 H24B 107.8 . . ?
C26 C27 N3 107.0(4) . . ?
C26 C27 H27 126.5 . . ?
N3 C27 H27 126.5 . . ?
C25 N4 C26 104.5(3) . . ?
N4 C25 N3 113.7(4) . . ?
N4 C25 H25 123.1 . . ?
N3 C25 H25 123.1 . . ?
O2 C28 C30 112.1(4) . . ?
O2 C28 H28A 109.2 . . ?
C30 C28 H28A 109.2 . . ?
O2 C28 H28B 109.2 . . ?
C30 C28 H28B 109.2 . . ?
H28A C28 H28B 107.9 . . ?
C30 C29 Cl6 127.7(6) . . ?
C30 C29 S2 113.9(5) . . ?
Cl6 C29 S2 118.3(5) . . ?
C29 C30 C31 109.9(6) . . ?
C29 C30 C28 126.4(6) . . ?
C31 C30 C28 123.7(6) . . ?
C32 C31 C30 112.8(7) . . ?
C32 C31 H31 123.6 . . ?
C30 C31 H31 123.6 . . ?
C31 C32 S2 113.5(7) . . ?
C31 C32 H32 123.3 . . ?
S2 C32 H32 123.3 . . ?
C34 C33 C35 118.1(3) . . ?
C34 C33 C36 123.1(3) . . ?
C35 C33 C36 118.8(3) . . ?
C35 C34 C33 120.5(4) 2_565 . ?
C35 C34 H34 119.8 2_565 . ?
C33 C34 H34 119.8 . . ?
C34 C35 C33 121.4(4) 2_565 . ?
C34 C35 H35 119.3 2_565 . ?
C33 C35 H35 119.3 . . ?
O4 C36 O3 123.6(4) . . ?
O4 C36 C33 122.5(4) . . ?
O3 C36 C33 113.9(3) . . ?
C39 C37 C38 119.4(3) . . ?
C39 C37 C40 118.8(3) . . ?
C38 C37 C40 121.8(4) . . ?
C39 C38 C37 120.1(4) 2_675 . ?
C39 C38 H38 119.9 2_675 . ?
C37 C38 H38 119.9 . . ?
C38 C39 C37 120.5(3) 2_675 . ?
C38 C39 H39 119.8 2_675 . ?
C37 C39 H39 119.8 . . ?
O6 C40 O5 124.4(4) . . ?
O6 C40 C37 121.8(4) . . ?
O5 C40 C37 113.9(3) . . ?
C9 N1 C11 104.6(3) . . ?
C9 N1 C8 128.0(3) . . ?
C11 N1 C8 127.3(3) . . ?
C9 N2 C10 104.9(3) . . ?
C25 N3 C27 105.2(4) . . ?
C25 N3 C24 128.7(4) . . ?
C27 N3 C24 126.0(3) . . ?
C27 C26 N4 109.6(4) . . ?
C27 C26 H26 125.2 . . ?
N4 C26 H26 125.2 . . ?
C7 O1 C12 112.9(3) . . ?
C23 O2 C28 113.7(4) . . ?
C36 O3 H3A 109.5 . . ?
C40 O5 H5A 109.5 . . ?
C29 S2 C32 89.8(4) . . ?
O2 C23 C24 106.9(3) . . ?
O2 C23 C17 112.8(3) . . ?
C24 C23 C17 110.5(3) . . ?
O2 C23 H23 108.9 . . ?
C24 C23 H23 108.9 . . ?
C17 C23 H23 108.9 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C14 C15A C16A S1A 13.7(18) . . . . ?
C15A C16A S1A C13 -9.8(17) . . . . ?
C14 C15B C16B S1B -0.2(17) . . . . ?
C6 C1 C2 C3 0.9(6) . . . . ?
C7 C1 C2 C3 -178.2(4) . . . . ?
C6 C1 C2 Cl1 177.7(3) . . . . ?
C7 C1 C2 Cl1 -1.4(5) . . . . ?
C1 C2 C3 C4 -2.2(7) . . . . ?
Cl1 C2 C3 C4 -179.1(4) . . . . ?
C2 C3 C4 C5 2.3(7) . . . . ?
C2 C3 C4 Cl2 -177.3(3) . . . . ?
C3 C4 C5 C6 -1.1(8) . . . . ?
Cl2 C4 C5 C6 178.5(4) . . . . ?
C4 C5 C6 C1 -0.3(8) . . . . ?
C2 C1 C6 C5 0.3(7) . . . . ?
C7 C1 C6 C5 179.4(4) . . . . ?
C2 C1 C7 O1 -148.8(4) . . . . ?
C6 C1 C7 O1 32.1(5) . . . . ?
C2 C1 C7 C8 92.9(4) . . . . ?
C6 C1 C7 C8 -86.2(4) . . . . ?
O1 C7 C8 N1 76.0(4) . . . . ?
C1 C7 C8 N1 -161.9(3) . . . . ?
N2 C10 C11 N1 -0.6(6) . . . . ?
C16A S1A C13 C14 -2.1(10) . . . . ?
C16A S1A C13 Cl3B -178.3(7) . . . . ?
C16B S1B C13 C14 2.9(8) . . . . ?
C16B S1B C13 Cl3A 179.8(9) . . . . ?
S1A C13 C14 C12 176.4(7) . . . . ?
Cl3A C13 C14 C12 7.9(13) . . . . ?
S1B C13 C14 C12 -175.8(6) . . . . ?
Cl3B C13 C14 C12 -7.7(9) . . . . ?
Cl3A C13 C14 C15B -180.0(10) . . . . ?
S1B C13 C14 C15B -3.7(9) . . . . ?
S1A C13 C14 C15A 8.3(10) . . . . ?
Cl3B C13 C14 C15A -175.8(7) . . . . ?
O1 C12 C14 C13 -115.4(6) . . . . ?
O1 C12 C14 C15B 72.4(7) . . . . ?
O1 C12 C14 C15A 49.7(9) . . . . ?
C16B C15B C14 C13 2.5(16) . . . . ?
C16B C15B C14 C12 176.2(12) . . . . ?
C16A C15A C14 C13 -12.7(13) . . . . ?
C16A C15A C14 C12 178.4(10) . . . . ?
C22 C17 C18 C19 -1.0(6) . . . . ?
C23 C17 C18 C19 -179.5(4) . . . . ?
C22 C17 C18 Cl4 179.2(3) . . . . ?
C23 C17 C18 Cl4 0.7(5) . . . . ?
C17 C18 C19 C20 -0.3(6) . . . . ?
Cl4 C18 C19 C20 179.5(3) . . . . ?
C18 C19 C20 C21 1.4(7) . . . . ?
C18 C19 C20 Cl5 -179.5(3) . . . . ?
C19 C20 C21 C22 -1.1(7) . . . . ?
Cl5 C20 C21 C22 179.7(4) . . . . ?
C18 C17 C22 C21 1.2(7) . . . . ?
C23 C17 C22 C21 179.7(4) . . . . ?
C20 C21 C22 C17 -0.2(8) . . . . ?
C26 N4 C25 N3 -0.2(5) . . . . ?
Cl6 C29 C30 C31 -179.7(5) . . . . ?
S2 C29 C30 C31 0.2(6) . . . . ?
Cl6 C29 C30 C28 2.5(8) . . . . ?
S2 C29 C30 C28 -177.6(4) . . . . ?
O2 C28 C30 C29 -123.7(6) . . . . ?
O2 C28 C30 C31 58.7(6) . . . . ?
C29 C30 C31 C32 0.1(9) . . . . ?
C28 C30 C31 C32 178.0(7) . . . . ?
C30 C31 C32 S2 -0.4(10) . . . . ?
C35 C33 C34 C35 -0.3(7) . . . 2_565 ?
C36 C33 C34 C35 179.4(4) . . . 2_565 ?
C34 C33 C35 C34 0.3(7) . . . 2_565 ?
C36 C33 C35 C34 -179.4(4) . . . 2_565 ?
C34 C33 C36 O4 -172.5(4) . . . . ?
C35 C33 C36 O4 7.1(6) . . . . ?
C34 C33 C36 O3 8.8(5) . . . . ?
C35 C33 C36 O3 -171.6(4) . . . . ?
C39 C37 C38 C39 -0.1(6) . . . 2_675 ?
C40 C37 C38 C39 179.1(4) . . . 2_675 ?
C38 C37 C39 C38 0.1(6) . . . 2_675 ?
C40 C37 C39 C38 -179.1(4) . . . 2_675 ?
C39 C37 C40 O6 12.6(6) . . . . ?
C38 C37 C40 O6 -166.6(4) . . . . ?
C39 C37 C40 O5 -166.1(4) . . . . ?
C38 C37 C40 O5 14.7(5) . . . . ?
N2 C9 N1 C11 -0.2(5) . . . . ?
N2 C9 N1 C8 178.7(3) . . . . ?
C10 C11 N1 C9 0.5(5) . . . . ?
C10 C11 N1 C8 -178.5(4) . . . . ?
C7 C8 N1 C9 -108.4(4) . . . . ?
C7 C8 N1 C11 70.3(5) . . . . ?
N1 C9 N2 C10 -0.1(5) . . . . ?
C11 C10 N2 C9 0.4(6) . . . . ?
N4 C25 N3 C27 -0.7(5) . . . . ?
N4 C25 N3 C24 176.0(3) . . . . ?
C26 C27 N3 C25 1.3(5) . . . . ?
C26 C27 N3 C24 -175.5(4) . . . . ?
C23 C24 N3 C25 -88.1(5) . . . . ?
C23 C24 N3 C27 88.0(4) . . . . ?
N3 C27 C26 N4 -1.5(5) . . . . ?
C25 N4 C26 C27 1.0(5) . . . . ?
C1 C7 O1 C12 75.9(4) . . . . ?
C8 C7 O1 C12 -163.8(3) . . . . ?
C14 C12 O1 C7 71.7(5) . . . . ?
C30 C28 O2 C23 73.3(6) . . . . ?
C30 C29 S2 C32 -0.3(5) . . . . ?
Cl6 C29 S2 C32 179.6(5) . . . . ?
C31 C32 S2 C29 0.4(8) . . . . ?
C28 O2 C23 C24 -164.2(4) . . . . ?
C28 O2 C23 C17 74.2(5) . . . . ?
N3 C24 C23 O2 75.8(4) . . . . ?
N3 C24 C23 C17 -161.2(3) . . . . ?
C22 C17 C23 O2 22.0(5) . . . . ?
C18 C17 C23 O2 -159.6(4) . . . . ?
C22 C17 C23 C24 -97.5(4) . . . . ?
C18 C17 C23 C24 80.9(4) . . . . ?

_refine_diff_density_max         0.724
_refine_diff_density_min         -0.501
_refine_diff_density_rms         0.097

