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_7247710
_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 H13 Cl3 N2 O S, C7 H3 Cl N O4'
_chemical_formula_sum            'C23 H16 Cl4 N3 O5 S'
_chemical_formula_weight         588.25
_chemical_name_common
'Tiaconazole-2-Chloro-4-nitrobenzoic acid 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   mixed
_audit_creation_method           SHELXL-2019/2
_audit_update_record
;
2023-07-31 deposited with the CCDC.	2023-11-14 downloaded from the CCDC.
;
_cell_angle_alpha                110.029(5)
_cell_angle_beta                 96.939(5)
_cell_angle_gamma                103.891(5)
_cell_formula_units_Z            2
_cell_length_a                   7.7627(5)
_cell_length_b                   11.9414(6)
_cell_length_c                   14.9934(7)
_cell_measurement_reflns_used    3939
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.4050
_cell_measurement_theta_min      2.8410
_cell_volume                     1235.79(13)
_computing_cell_refinement       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_collection       'CrystalClear-SM Expert 2.1 b28 (Rigaku, 2013)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick, 2015)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.861
_diffrn_measured_fraction_theta_max 0.731
_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    -30.00  70.00   0.50   10.00    --  -20.00  60.00   0.00  200
  2  \w    -30.00  70.00   0.50   10.00    --  -20.00  60.00  90.00  200
  3  \w   -110.00 -10.00   0.50   10.00    --  -20.00 -60.00 180.00  200
  4  \w   -110.00 -10.00   0.50   10.00    --  -20.00 -60.00 180.00  200
;
_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_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0177153000
_diffrn_orient_matrix_UB_12      -0.0095829000
_diffrn_orient_matrix_UB_13      -0.0500157000
_diffrn_orient_matrix_UB_21      -0.0237310000
_diffrn_orient_matrix_UB_22      -0.0655797000
_diffrn_orient_matrix_UB_23      -0.0128564000
_diffrn_orient_matrix_UB_31      -0.0918952000
_diffrn_orient_matrix_UB_32      -0.0022438000
_diffrn_orient_matrix_UB_33      0.0008814000
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1408
_diffrn_reflns_av_unetI/netI     0.1240
_diffrn_reflns_Laue_measured_fraction_full 0.861
_diffrn_reflns_Laue_measured_fraction_max 0.731
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            12445
_diffrn_reflns_point_group_measured_fraction_full 0.861
_diffrn_reflns_point_group_measured_fraction_max 0.731
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.400
_diffrn_reflns_theta_min         1.483
_diffrn_source                   MicroMax003_Mo
_exptl_absorpt_coefficient_mu    0.605
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.33594
_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    1.581
_exptl_crystal_description       plate
_exptl_crystal_F_000             598
_exptl_crystal_size_max          0.270
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.090
_refine_diff_density_max         0.593
_refine_diff_density_min         -0.883
_refine_diff_density_rms         0.145
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     334
_refine_ls_number_reflns         5965
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.1344
_refine_ls_R_factor_gt           0.0874
_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^)+(0.1343P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2182
_refine_ls_wR_factor_ref         0.2393
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3665
_reflns_number_total             5965
_reflns_threshold_expression     'I > 2\s(I)'
_twin_special_details
;
Component 2 rotated by 10.7356\% 
around [-0.90 0.44 -0.03] (reciprocal) or [-1.00 0.02 -0.07] (direct)
;
_cod_data_source_file            d3ce00948c2.cif
_cod_data_source_block           TCZ-CNBA
_cod_depositor_comments
'Adding full bibliography for 7247709--7247724.cif.'
_cod_database_code               7247710
_shelx_shelxl_version_number     2019/2
_shelx_estimated_absorpt_t_min   0.854
_shelx_estimated_absorpt_t_max   0.948
_oxdiff_exptl_absorpt_empirical_full_min 0.504
_oxdiff_exptl_absorpt_empirical_full_max 2.303
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_twin_items               2
_oxdiff_twin_integration_method  simultaneous
_shelx_res_checksum              33282