Development of new multicomponent crystals of the antifungal drug tioconazole and the assessment of their biopharmaceutical attributes
Madhesiya, Avinash; Dash, Sibananda G.; Gupta, Princi; Akhir, Abdul; Saxena, Deepanshi; Maitra, Rahul; Chopra, Sidharth; Thakur, Tejender S.; CrystEngComm 25 (2023) 6758–6776; doi:10.1039/D3CE00948C

data_7247718
_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 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
_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   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                82.360(9)
_cell_angle_beta                 88.440(6)
_cell_angle_gamma                88.592(3)
_cell_formula_units_Z            2
_cell_length_a                   8.4631(3)
_cell_length_b                   12.0147(6)
_cell_length_c                   21.5955(18)
_cell_measurement_reflns_used    15978
_cell_measurement_temperature    297(2)
_cell_measurement_theta_max      78.8530
_cell_measurement_theta_min      2.0630
_cell_volume                     2175.1(2)
_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    'SHELXT-2018/2 (Sheldrick, 2015)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      297(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.965
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w     39.00  94.00   0.50    0.13    --   47.33-128.00 -15.00  110
  2  \w     54.00  79.00   0.50    0.53    --  113.25-128.00 -15.00   50
  3  \w     47.00  79.00   0.50    0.53    --  113.25-125.00 120.00   64
  4  \w     84.00 109.00   0.50    0.53    --  113.25-125.00 120.00   50
  5  \w     90.00 125.00   0.50    0.53    --  113.25-144.00 174.00   70
  6  \w     50.00 103.00   0.50    0.13    --   47.33-144.00 174.00  106
  7  \w     83.00 109.00   0.50    0.53    --  113.25-125.00  90.00   52
  8  \w     45.00  81.00   0.50    0.53    --  113.25-125.00  90.00   72
  9  \w     59.00 107.00   0.50    0.53    --  113.25-103.00 -21.12   96
 10  \w     81.00 106.00   0.50    0.53    --  113.25 -95.00 -30.00   50
 11  \w     44.00 106.00   0.50    0.53    --  113.25 -95.00   0.00  124
 12  \w     52.00  86.00   0.50    0.53    --  113.25 -95.00 120.00   68
 13  \w     57.00 106.00   0.50    0.53    --  113.25 -95.00-120.00   98
 14  \w     80.00 106.00   0.50    0.53    --  113.25 -95.00-150.00   52
 15  \w     43.00  69.00   0.50    0.53    --  113.25 -95.00-150.00   52
 16  \w     44.00 108.00   0.50    0.53    --  113.25-108.00-177.64  128
 17  \w     75.00 106.00   0.50    0.53    --  113.25 -95.00-180.00   62
 18  \w     46.00 106.00   0.50    0.53    --  113.25 -95.00 -90.00  120
 19  \w     46.00  92.00   0.50    0.53    --  113.25 -95.00 -60.00   92
 20  \w     45.00  73.00   0.50    0.53    --  113.25 -95.00  30.00   56
 21  \w     77.00 106.00   0.50    0.53    --  113.25 -95.00  60.00   58
 22  \w     53.00  98.00   0.50    0.53    --  113.25 -95.00 150.00   90
 23  \w     43.00  69.00   0.50    0.53    --  113.25 -61.00 150.00   52
 24  \w     44.00  72.00   0.50    0.53    --  113.25 -61.00  90.00   56
 25  \w     42.00  68.00   0.50    0.53    --  113.25 -61.00  30.00   52
 26  \w     43.00  71.00   0.50    0.53    --  113.25 -61.00 -60.00   56
 27  \w     44.00  73.00   0.50    0.53    --  113.25 -61.00-150.00   58
 28  \w     46.00  71.00   0.50    0.53    --  113.25 -61.00-180.00   50
 29  \w    100.00 173.00   0.50    0.53    --  113.25  15.00 -60.00  146
 30  \w    110.00 178.00   0.50    0.53    --  113.25  30.00-120.00  136
 31  \w    102.00 157.00   0.50    0.53    --  113.25  30.00  30.00  110
 32  \w    124.00 150.00   0.50    0.53    --  113.25  45.00  60.00   52
 33  \w    104.00 139.00   0.50    0.53    --  113.25  30.00 120.00   70
 34  \w    102.00 170.00   0.50    0.53    --  113.25  45.00 150.00  136
 35  \w    101.00 144.00   0.50    0.53    --  113.25  15.00   0.00   86
 36  \w    100.00 158.00   0.50    0.53    --  113.25  15.00 -30.00  116
 37  \w    106.00 178.00   0.50    0.53    --  113.25  15.00-150.00  144
 38  \w    102.00 127.00   0.50    0.53    --  113.25 144.00-131.00   50
 39  \w    119.00 159.00   0.50    0.53    --  113.25 128.00  59.00   80
 40  \w    -26.00   9.00   0.50    0.13    --   47.33 -19.00   0.00   70
 41  \w   -118.00 -30.00   0.50    0.13    --  -47.33 -77.00-120.00  176
 42  \w   -141.00-116.00   0.50    0.53    --  -91.75-128.00 -15.00   50
 43  \w    -99.00 -73.00   0.50    0.13    --  -47.33-128.00 -15.00   52
 44  \w   -116.00 -67.00   0.50    0.13    --  -47.33-144.00 174.00   98
 45  \w   -131.00-106.00   0.50    0.53    --  -91.75-144.00 174.00   50
 46  \w   -164.00-138.00   0.50    0.53    --  -91.75 -30.00  30.00   52
 47  \w    -49.00 -21.00   0.50    0.53    --  -91.75  45.00-180.00   56
 48  \w    -22.00  28.00   0.50    0.13    --  -47.33  19.00-180.00  100
 49  \w     -8.00  25.00   0.50    0.13    --  -47.33  19.00-150.00   66
 50  \w    -24.00  14.00   0.50    0.13    --  -47.33  19.00   0.00   76
 51  \w    -41.00  23.00   0.50    0.13    --  -47.33  38.00  90.00  128
 52  \w    -74.00 -49.00   0.50    0.53    --  -91.75 128.00  59.00   50
 53  \w    -47.00 -22.00   0.50    0.13    --  -47.33 128.00  59.00   50
 54  \w    -86.00 -61.00   0.50    0.13    --  -47.33 144.00-131.00   50
 55  \w    -86.00 -61.00   0.50    0.53    --  -91.75 144.00-131.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       '\w scans'
_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_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.1023
_diffrn_reflns_av_unetI/netI     0.0789
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.965
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            29542
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.883
_diffrn_reflns_theta_min         2.065
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    5.451
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.36691
_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    1.462
_exptl_crystal_description       plate
_exptl_crystal_F_000             980
_exptl_crystal_size_max          0.270
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.435
_refine_diff_density_min         -0.673
_refine_diff_density_rms         0.093
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     600
_refine_ls_number_reflns         9156
_refine_ls_number_restraints     8
_refine_ls_restrained_S_all      1.100
_refine_ls_R_factor_all          0.1016
_refine_ls_R_factor_gt           0.0860
_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/[\s^2^(Fo^2^)+(0.1756P)^2^+0.2368P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2464
_refine_ls_wR_factor_ref         0.2716
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6864
_reflns_number_total             9156
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ce00948c2.cif
_cod_data_source_block           TCZ-SULH
_cod_depositor_comments
'Adding full bibliography for 7247709--7247724.cif.'
_cod_database_code               7247718
_shelx_shelxl_version_number     2019/2
_shelx_estimated_absorpt_t_min   0.321
_shelx_estimated_absorpt_t_max   0.899
_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
;
_shelx_res_checksum              89338