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_7247720
_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         '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
_chemical_name_common            'Tioconzaole sulfate (2:1) salt heptahydrate'
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_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
;
2023-09-22 deposited with the CCDC.	2023-11-14 downloaded from the CCDC.
;
_cell_angle_alpha                86.078(2)
_cell_angle_beta                 77.368(2)
_cell_angle_gamma                66.240(3)
_cell_formula_units_Z            2
_cell_length_a                   10.5568(3)
_cell_length_b                   10.9083(3)
_cell_length_c                   20.8988(4)
_cell_measurement_reflns_used    18112
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      79.3000
_cell_measurement_theta_min      2.1740
_cell_volume                     2148.81(11)
_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      100(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 0.962
_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    -24.00  24.00   0.50    0.09    --  -47.08  19.00  60.00   96
  2  \w    -62.00  24.00   0.50    0.09    --  -47.08  57.00  60.00  172
  3  \w    -17.00  25.00   0.50    0.09    --  -47.08  38.00 -60.00   84
  4  \w    -25.00  25.00   0.50    0.09    --  -47.08  38.00-180.00  100
  5  \w    130.00 177.00   0.50    0.37    --  113.25  77.00 -30.00   94
  6  \w    140.00 177.00   0.50    0.37    --  113.25  45.00   0.00   74
  7  \w     96.00 121.00   0.50    0.37    --  113.25  77.00 -30.00   50
  8  \w    102.00 177.00   0.50    0.37    --  113.25  61.00 -60.00  150
  9  \w     98.00 152.00   0.50    0.37    --  113.25  61.00-120.00  108
 10  \w    102.00 138.00   0.50    0.37    --  113.25  45.00-120.00   72
 11  \w    103.00 169.00   0.50    0.37    --  113.25  30.00 -60.00  132
 12  \w    101.00 155.00   0.50    0.37    --  113.25  30.00  30.00  108
 13  \w    101.00 178.00   0.50    0.37    --  113.25  30.00  60.00  154
 14  \w    142.00 167.00   0.50    0.37    --  113.25  30.00  90.00   50
 15  \w    105.00 143.00   0.50    0.37    --  113.25  30.00 120.00   76
 16  \w    106.00 178.00   0.50    0.37    --  113.25  30.00 150.00  144
 17  \w    102.00 140.00   0.50    0.37    --  113.25  30.00  90.00   76
 18  \w    149.00 176.00   0.50    0.37    --  113.25  94.00 -19.00   54
 19  \w     43.00  69.00   0.50    0.37    --  113.25 -61.00 120.00   52
 20  \w     67.00  92.00   0.50    0.37    --  113.25 -77.00  90.00   50
 21  \w     43.00  70.00   0.50    0.37    --  113.25 -61.00  90.00   54
 22  \w     42.00  73.00   0.50    0.37    --  113.25 -61.00  60.00   62
 23  \w     47.00  73.00   0.50    0.37    --  113.25 -61.00 -60.00   52
 24  \w     42.00  68.00   0.50    0.37    --  113.25 -61.00-120.00   52
 25  \w     59.00  95.00   0.50    0.37    --  113.25 -94.00-129.00   72
 26  \w     78.00 109.00   0.50    0.37    --  113.25-114.00-150.00   62
 27  \w     45.00  71.00   0.50    0.37    --  113.25-114.00-150.00   52
 28  \w     75.00 106.00   0.50    0.37    --  113.25 -99.00 -90.50   62
 29  \w     79.00 104.00   0.50    0.37    --  113.25 -95.00 -30.00   50
 30  \w     54.00  93.00   0.50    0.37    --  113.25 -95.00 -90.00   78
 31  \w     43.00  93.00   0.50    0.37    --  113.25 -95.00  60.00  100
 32  \w     49.00 107.00   0.50    0.37    --  113.25-104.00 123.35  116
 33  \w     53.00  94.00   0.50    0.37    --  113.25 -95.00 150.00   82
 34  \w     73.00 123.00   0.50    0.37    --  113.25-140.00 118.49  100
 35  \w     57.00  96.00   0.50    0.37    --  113.25 -95.00   0.00   78
 36  \w     46.00 103.00   0.50    0.37    --  113.25 -95.00  30.00  114
 37  \w     46.00  72.00   0.50    0.37    --  113.25 -95.00 -30.00   52
 38  \w     44.00 104.00   0.50    0.37    --  113.25 -95.00 -60.00  120
 39  \w     59.00 106.00   0.50    0.37    --  113.25 -95.00-150.00   94
 40  \w     53.00 100.00   0.50    0.37    --  113.25 -95.00-180.00   94
 41  \w     35.00  89.00   0.50    0.09    --   47.08-125.00-120.00  108
 42  \w     40.00  78.00   0.50    0.09    --   47.08 -94.00-129.00   76
 43  \w    -12.00  31.00   0.50    0.09    --   47.08 -94.00-129.00   86
 44  \w    -45.00 -18.00   0.50    0.09    --  -47.08  94.00 -19.00   54
 45  \w    -13.00  12.00   0.50    0.09    --  -47.08  94.00 -19.00   50
 46  \w    -49.00 -21.00   0.50    0.37    --  -91.75  45.00  60.00   56
 47  \w    -74.00 -49.00   0.50    0.37    --  -91.75  94.00 -19.00   50
 48  \w    -49.00 -21.00   0.50    0.37    --  -91.75  45.00   0.00   56
 49  \w   -115.00 -34.00   0.50    0.09    --  -47.08 -57.00 -90.00  162
 50  \w   -163.00-107.00   0.50    0.37    --  -91.75 -95.00 -30.00  112
 51  \w   -123.00 -91.00   0.50    0.37    --  -91.75 -94.00-129.00   64
;
_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      0.0804003000
_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_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0649
_diffrn_reflns_av_unetI/netI     0.0610
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.962
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            28515
_diffrn_reflns_point_group_measured_fraction_full 0.696
_diffrn_reflns_point_group_measured_fraction_max 0.657
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         80.287
_diffrn_reflns_theta_min         2.167
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    5.575
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.49291
_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    1.545
_exptl_crystal_description       plate
_exptl_crystal_F_000             1032
_exptl_crystal_size_max          0.270
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.821
_refine_diff_density_min         -0.690
_refine_diff_density_rms         0.117
_refine_ls_abs_structure_details
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   0.300(18)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1176
_refine_ls_number_reflns         12321
_refine_ls_number_restraints     55
_refine_ls_restrained_S_all      1.101
_refine_ls_R_factor_all          0.0773
_refine_ls_R_factor_gt           0.0677
_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^)+(0.1495P)^2^+0.2603P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1937
_refine_ls_wR_factor_ref         0.2060
_reflns_Friedel_coverage         0.365
_reflns_Friedel_fraction_full    0.397
_reflns_Friedel_fraction_max     0.351
_reflns_number_gt                10349
_reflns_number_total             12321
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ce00948c2.cif
_cod_data_source_block           TCZ-SULH2
_cod_depositor_comments
'Adding full bibliography for 7247709--7247724.cif.'
_cod_original_cell_volume        2148.82(11)
_cod_database_code               7247720
_shelx_shelxl_version_number     2019/2
_shelx_estimated_absorpt_t_min   0.314
_shelx_estimated_absorpt_t_max   0.897
_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
;
_shelx_res_checksum              86500