#------------------------------------------------------------------------------
#$Date: 2024-01-06 10:01:35 +0200 (Sat, 06 Jan 2024) $
#$Revision: 288801 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/77/7247714.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7247714
loop_
_publ_author_name
'Madhesiya, Avinash'
'Dash, Sibananda G.'
'Gupta, Princi'
'Akhir, Abdul'
'Saxena, Deepanshi'
'Maitra, Rahul'
'Chopra, Sidharth'
'Thakur, Tejender S.'
_publ_section_title
;
 Development of new multicomponent crystals of the antifungal drug
 tioconazole and the assessment of their biopharmaceutical attributes
;
_journal_issue                   48
_journal_name_full               CrystEngComm
_journal_page_first              6758
_journal_page_last               6776
_journal_paper_doi               10.1039/D3CE00948C
_journal_volume                  25
_journal_year                    2023
_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
_chemical_name_common            'Tioconazole-Nicotinic acid cocrystal'
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   direct
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2023-07-31 deposited with the CCDC.	2023-11-14 downloaded from the CCDC.
;
_cell_angle_alpha                97.644(2)
_cell_angle_beta                 99.212(2)
_cell_angle_gamma                90.462(2)
_cell_formula_units_Z            4
_cell_length_a                   8.0219(2)
_cell_length_b                   12.3226(3)
_cell_length_c                   23.9838(5)
_cell_measurement_reflns_used    30291
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      72.5670
_cell_measurement_theta_min      3.6060
_cell_volume                     2318.40(10)
_computing_cell_refinement       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_collection       'CrystalClear-SM Expert 2.1 b28 (Rigaku, 2013)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SIR-2011 (Burla et al., 2012)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.960
_diffrn_measurement_device
;
AFC12 (Right): Kappa 3 circle
;
_diffrn_measurement_device_type
;
Rigaku Saturn724+ (4x4 bin mode)
;
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support Loop
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.1407
_diffrn_reflns_av_unetI/netI     0.0693
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.960
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            48662
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.960
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.776
_diffrn_reflns_theta_min         3.621
_diffrn_source                   MicroMax003_Cu
_diffrn_source_current           0.6
_diffrn_source_power             0.0
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    4.677
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.13435
_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_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.463
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1048
_exptl_crystal_size_max          0.870
_exptl_crystal_size_mid          0.380
_exptl_crystal_size_min          0.120
_refine_diff_density_max         0.814
_refine_diff_density_min         -0.798
_refine_diff_density_rms         0.147
_refine_ls_extinction_coef       0.0122(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     582
_refine_ls_number_reflns         8855
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.086
_refine_ls_R_factor_all          0.0813
_refine_ls_R_factor_gt           0.0730
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1318P)²+0.5409P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1879
_refine_ls_wR_factor_ref         0.2019
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7791
_reflns_number_total             8855
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3ce00948c2.cif
_cod_data_source_block           TCZ_NICA
_cod_depositor_comments
'Adding full bibliography for 7247709--7247724.cif.'
_cod_database_code               7247714
_shelx_shelxl_version_number     2018/3
_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.
;
_shelx_estimated_absorpt_t_min   0.106
_shelx_estimated_absorpt_t_max   0.604
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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 . . . . .
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'
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_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_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) . . . . ?
