#------------------------------------------------------------------------------
#$Date: 2024-01-06 10:01:35 +0200 (Sat, 06 Jan 2024) $
#$Revision: 288801 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/77/7247719.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_7247719
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 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
_chemical_name_common            'Tioconazole-L-tartrate 1:1 salt hydrate'
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2019/2
_audit_update_record
;
2023-09-21 deposited with the CCDC.	2023-11-14 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.60280(10)
_cell_length_b                   9.94440(10)
_cell_length_c                   35.6016(4)
_cell_measurement_reflns_used    54997
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      76.6930
_cell_measurement_theta_min      2.4770
_cell_volume                     2691.67(5)
_computing_cell_refinement       'CrysAlisPro 1.171.42.88a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.88a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.88a (Rigaku OD, 2023)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_structure_solution    'SHELXL-2018/2 (Sheldrick, 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.987
_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_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_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_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.1116
_diffrn_reflns_av_unetI/netI     0.0270
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       43
_diffrn_reflns_limit_l_min       -44
_diffrn_reflns_number            93425
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.786
_diffrn_reflns_theta_min         2.482
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    4.312
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.42537
_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_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.477
_exptl_crystal_description       plate
_exptl_crystal_F_000             1237
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.080
_refine_diff_density_max         0.327
_refine_diff_density_min         -0.277
_refine_diff_density_rms         0.056
_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)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.146
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     366
_refine_ls_number_reflns         5579
_refine_ls_number_restraints     8
_refine_ls_restrained_S_all      1.151
_refine_ls_R_factor_all          0.0641
_refine_ls_R_factor_gt           0.0618
_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)+(0.0357P)²+3.1046P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1301
_refine_ls_wR_factor_ref         0.1312
_reflns_Friedel_coverage         0.714
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.949
_reflns_number_gt                5273
_reflns_number_total             5579
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3ce00948c2.cif
_cod_data_source_block           TCA-LTAH
_cod_depositor_comments
'Adding full bibliography for 7247709--7247724.cif.'
_cod_database_code               7247719
_shelx_shelxl_version_number     2019/2
_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   0.465
_shelx_estimated_absorpt_t_max   0.724
_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
;
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'
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 . . . .
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'
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_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_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) . . . . ?
