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_7247716
_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         'C20 H13 Cl3 N2 O1 S, 0.5(C8 H6 O4)'
_chemical_formula_sum            'C20 H16 Cl3 N2 O3 S'
_chemical_formula_weight         470.76
_chemical_name_common
'Tioconazole-ter-pthalic acid (1:0.5) 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
_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                83.111(3)
_cell_angle_beta                 83.102(3)
_cell_angle_gamma                75.116(3)
_cell_formula_units_Z            2
_cell_length_a                   7.4880(2)
_cell_length_b                   11.3843(4)
_cell_length_c                   13.0280(4)
_cell_measurement_reflns_used    13081
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      72.2920
_cell_measurement_theta_min      3.4120
_cell_volume                     1060.94(6)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrystalClear-SM Expert 2.1 b28 (Rigaku, 2013)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_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    'SHELXS-2013/1 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.960
_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   -130.00 -10.00   1.00    6.00    --  -40.00 -72.00   0.00  120
  2  \w   -130.00 -10.00   1.00    6.00    --  -40.00 -72.00  70.00  120
  3  \w   -130.00 -10.00   1.00    6.00    --  -40.00 -72.00 140.00  120
  4  \w   -130.00 -10.00   1.00    6.00    --  -40.00 -72.00 210.00  120
  5  \w   -130.00 -10.00   1.00    6.00    --  -40.00 -72.00 280.00  120
  6  \w   -130.00  50.00   1.00    6.00    --  -40.00   0.00   0.00  180
  7  \w   -100.00  20.00   1.00    6.00    --  -70.00  72.00   0.00  120
  8  \w   -100.00  20.00   1.00    6.00    --  -70.00  72.00  70.00  120
  9  \w   -100.00  20.00   1.00    6.00    --  -70.00  72.00 140.00  120
 10  \w   -100.00  20.00   1.00    6.00    --  -70.00  72.00 210.00  120
 11  \w   -100.00  20.00   1.00    6.00    --  -70.00  72.00 280.00  120
 12  \w   -160.00  20.00   1.00    6.00    --  -70.00   0.00   0.00  180
 13  \w   -190.00 -70.00   1.00    6.00    -- -100.00 -72.00   0.00  120
 14  \w   -190.00 -70.00   1.00    6.00    -- -100.00 -72.00  70.00  120
 15  \w   -190.00 -70.00   1.00    6.00    -- -100.00 -72.00 140.00  120
 16  \w   -190.00 -70.00   1.00    6.00    -- -100.00 -72.00 210.00  120
 17  \w   -190.00 -70.00   1.00    6.00    -- -100.00 -72.00 280.00  120
 18  \w   -130.00 -10.00   1.00    6.00    -- -100.00  72.00   0.00  120
 19  \w   -130.00 -10.00   1.00    6.00    -- -100.00  72.00  70.00  120
 20  \w   -130.00 -10.00   1.00    6.00    -- -100.00  72.00 140.00  120
 21  \w   -130.00 -10.00   1.00    6.00    -- -100.00  72.00 210.00  120
 22  \w   -130.00 -10.00   1.00    6.00    -- -100.00  72.00 280.00  120
 23  \w   -190.00 -10.00   1.00    6.00    -- -100.00   0.00   0.00  180
;
_diffrn_measurement_device
;
AFC12 (Right): Kappa 3 circle
;
_diffrn_measurement_device_type
;
Rigaku Saturn724+ (4x4 bin mode)
;
_diffrn_measurement_method       'profile data from \w-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  0.1180
_diffrn_reflns_av_unetI/netI     0.0546
_diffrn_reflns_Laue_measured_fraction_full 0.982
_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       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            21968
_diffrn_reflns_point_group_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.960
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.711
_diffrn_reflns_theta_min         3.432
_diffrn_source                   MicroMax003_Mo
_diffrn_source_current           0.6
_diffrn_source_power             0.0
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    5.044
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.49881
_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    1.474
_exptl_crystal_description       block
_exptl_crystal_F_000             482
_exptl_crystal_size_max          0.380
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.240
_refine_diff_density_max         0.440
_refine_diff_density_min         -0.588
_refine_diff_density_rms         0.109
_refine_ls_extinction_coef       0.0052(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     265
_refine_ls_number_reflns         4055
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.075
_refine_ls_R_factor_all          0.0758
_refine_ls_R_factor_gt           0.0679
_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^)+(0.1192P)^2^+0.2409P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1792
_refine_ls_wR_factor_ref         0.1925
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3406
_reflns_number_total             4055
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ce00948c2.cif
_cod_data_source_block           TCZ-TPTH2
_cod_depositor_comments
'Adding full bibliography for 7247709--7247724.cif.'
_cod_database_code               7247716
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.250
_shelx_estimated_absorpt_t_max   0.377
_shelx_res_checksum              87019