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_7247721
_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), C2 O4, 4(H2 O)'
_chemical_formula_sum            'C34 H36 Cl6 N4 O10 S2'
_chemical_formula_weight         937.49
_chemical_name_common            'Tioconazole-oxalate (2:1)salt tetrahydrate'
_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                73.851(2)
_cell_angle_beta                 78.295(2)
_cell_angle_gamma                85.648(2)
_cell_formula_units_Z            2
_cell_length_a                   7.65410(10)
_cell_length_b                   15.9993(4)
_cell_length_c                   17.8133(5)
_cell_measurement_reflns_used    18144
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      78.8510
_cell_measurement_theta_min      2.6290
_cell_volume                     2051.33(9)
_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      N~2~
_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 1.000
_diffrn_measured_fraction_theta_max 0.975
_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    -48.00 -21.00   0.50    0.43    --  -91.75  45.00  60.00   54
  2  \w   -102.00 -43.00   0.50    0.43    --  -91.75  77.00   0.00  118
  3  \w    -48.00 -21.00   0.50    0.43    --  -91.75  45.00 -60.00   54
  4  \w    -49.00 -24.00   0.50    0.43    --  -91.75  45.00 -90.00   50
  5  \w    -41.00  26.00   0.50    0.11    --  -47.33  38.00-120.00  134
  6  \w    -16.00  11.00   0.50    0.11    --  -47.33  19.00-180.00   54
  7  \w    -39.00  26.00   0.50    0.11    --  -47.33  38.00   0.00  130
  8  \w    -17.00  20.00   0.50    0.11    --  -47.33  19.00 120.00   74
  9  \w    -18.00  21.00   0.50    0.11    --  -47.33  19.00 150.00   78
 10  \w    -74.00   1.00   0.50    0.11    --  -47.33  96.00  61.00  150
 11  \w    -84.00 -13.00   0.50    0.11    --  -47.33 125.00  90.00  142
 12  \w    -67.00 -41.00   0.50    0.43    --  -91.75  96.00  61.00   52
 13  \w   -147.00-122.00   0.50    0.43    --  -91.75 -96.00 -48.00   50
 14  \w     43.00  72.00   0.50    0.43    --  113.25 -61.00  90.00   58
 15  \w     44.00 107.00   0.50    0.43    --  113.25 -77.00  60.00  126
 16  \w     82.00 107.00   0.50    0.43    --  113.25 -77.00 -90.00   50
 17  \w     43.00  68.00   0.50    0.43    --  113.25 -77.00 -90.00   50
 18  \w     42.00  73.00   0.50    0.43    --  113.25 -61.00  60.00   62
 19  \w     46.00  72.00   0.50    0.43    --  113.25 -61.00 150.00   52
 20  \w     45.00  72.00   0.50    0.43    --  113.25 -61.00   0.00   54
 21  \w     96.00 176.00   0.50    0.43    --  113.25 125.00  90.00  160
 22  \w    106.00 171.00   0.50    0.43    --  113.25  96.00  61.00  130
 23  \w     43.00  71.00   0.50    0.43    --  113.25 -61.00-150.00   56
 24  \w     42.00  67.00   0.50    0.43    --  113.25 -61.00-120.00   50
 25  \w     51.00  76.00   0.50    0.43    --  113.25 -95.00-150.00   50
 26  \w     62.00 111.00   0.50    0.43    --  113.25-125.00 -30.00   98
 27  \w     66.00 106.00   0.50    0.43    --  113.25-110.00  40.82   80
 28  \w     44.00 111.00   0.50    0.43    --  113.25-125.00  90.00  134
 29  \w     68.00 109.00   0.50    0.43    --  113.25-115.00  84.49   82
 30  \w     45.00  70.00   0.50    0.43    --  113.25 -95.00 150.00   50
 31  \w     81.00 106.00   0.50    0.43    --  113.25 -95.00 150.00   50
 32  \w     49.00  85.00   0.50    0.43    --  113.25 -95.00   0.00   72
 33  \w     68.00 103.00   0.50    0.43    --  113.25 -96.00 -48.00   70
 34  \w     79.00 106.00   0.50    0.43    --  113.25 -95.00-120.00   54
 35  \w     42.00  75.00   0.50    0.43    --  113.25 -95.00-120.00   66
 36  \w     46.00  72.00   0.50    0.43    --  113.25 -95.00-180.00   52
 37  \w     80.00 106.00   0.50    0.43    --  113.25 -95.00-150.00   52
 38  \w     79.00 105.00   0.50    0.43    --  113.25 -95.00-180.00   52
 39  \w      1.00  41.00   0.50    0.11    --   47.33 -96.00 -48.00   80
 40  \w     71.00  96.00   0.50    0.43    --  113.25 -95.00  90.00   50
 41  \w     79.00 105.00   0.50    0.43    --  113.25 -95.00 120.00   52
 42  \w    101.00 156.00   0.50    0.43    --  113.25  15.00-120.00  110
 43  \w    114.00 174.00   0.50    0.43    --  113.25  45.00-120.00  120
 44  \w    101.00 176.00   0.50    0.43    --  113.25  45.00 -30.00  150
 45  \w    127.00 164.00   0.50    0.43    --  113.25  45.00 -60.00   74
 46  \w     98.00 173.00   0.50    0.43    --  113.25  61.00   0.00  150
 47  \w    119.00 177.00   0.50    0.43    --  113.25  30.00 -90.00  116
 48  \w    105.00 150.00   0.50    0.43    --  113.25  45.00  60.00   90
 49  \w    118.00 144.00   0.50    0.43    --  113.25  45.00 120.00   52
 50  \w     97.00 170.00   0.50    0.43    --  113.25  61.00 150.00  146
;
_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      -0.0367903000
_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_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0699
_diffrn_reflns_av_unetI/netI     0.0597
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            28902
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.808
_diffrn_reflns_theta_min         2.630
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    5.284
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.61561
_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            'clear colourless'
_exptl_crystal_density_diffrn    1.518
_exptl_crystal_description       plate
_exptl_crystal_F_000             964
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.030
_refine_diff_density_max         0.543
_refine_diff_density_min         -0.498
_refine_diff_density_rms         0.080
_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     555
_refine_ls_number_reflns         8721
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.095
_refine_ls_R_factor_all          0.0555
_refine_ls_R_factor_gt           0.0492
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0822P)^2^+0.4318P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1362
_refine_ls_wR_factor_ref         0.1414
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7474
_reflns_number_total             8721
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ce00948c2.cif
_cod_data_source_block           TCZ_OXAH
_cod_depositor_comments
'Adding full bibliography for 7247709--7247724.cif.'
_cod_database_code               7247721
_shelx_shelxl_version_number     2019/2
_shelx_estimated_absorpt_t_min   0.505
_shelx_estimated_absorpt_t_max   0.858
_shelx_res_checksum              69457