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_7247722
_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 H14 Cl3 N2 O S, C4 H3 O4, O'
_chemical_formula_sum            'C20 H17 Cl3 N2 O6 S'
_chemical_formula_weight         519.77
_chemical_name_common            'Tioconazole-Fumerate salt monohydrate'
_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
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   direct
_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                94.572(2)
_cell_angle_beta                 98.318(2)
_cell_angle_gamma                94.709(3)
_cell_formula_units_Z            2
_cell_length_a                   7.4874(2)
_cell_length_b                   8.0833(3)
_cell_length_c                   19.8791(5)
_cell_measurement_reflns_used    13045
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      71.9910
_cell_measurement_theta_min      2.2500
_cell_volume                     1181.34(6)
_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-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 0.962
_diffrn_measured_fraction_theta_max 0.934
_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    4.00    --  -40.00 -72.00   0.00  120
  2  \w   -130.00 -10.00   1.00    4.00    --  -40.00 -72.00  70.00  120
  3  \w   -130.00 -10.00   1.00    4.00    --  -40.00 -72.00 140.00  120
  4  \w   -130.00 -10.00   1.00    4.00    --  -40.00 -72.00 210.00  120
  5  \w   -130.00 -10.00   1.00    4.00    --  -40.00 -72.00 280.00  120
  6  \w   -130.00  50.00   1.00    4.00    --  -40.00   0.00   0.00  180
  7  \w   -100.00  20.00   1.00    4.00    --  -70.00  72.00   0.00  120
  8  \w   -100.00  20.00   1.00    4.00    --  -70.00  72.00  70.00  120
  9  \w   -100.00  20.00   1.00    4.00    --  -70.00  72.00 140.00  120
 10  \w   -100.00  20.00   1.00    4.00    --  -70.00  72.00 210.00  120
 11  \w   -100.00  20.00   1.00    4.00    --  -70.00  72.00 280.00  120
 12  \w   -160.00  20.00   1.00    4.00    --  -70.00   0.00   0.00  180
 13  \w   -190.00 -70.00   1.00    4.00    -- -100.00 -72.00   0.00  120
 14  \w   -190.00 -70.00   1.00    4.00    -- -100.00 -72.00  70.00  120
 15  \w   -190.00 -70.00   1.00    4.00    -- -100.00 -72.00 140.00  120
 16  \w   -190.00 -70.00   1.00    4.00    -- -100.00 -72.00 210.00  120
 17  \w   -190.00 -70.00   1.00    4.00    -- -100.00 -72.00 280.00  120
 18  \w   -130.00 -10.00   1.00    4.00    -- -100.00  72.00   0.00  120
 19  \w   -130.00 -10.00   1.00    4.00    -- -100.00  72.00  70.00  120
 20  \w   -130.00 -10.00   1.00    4.00    -- -100.00  72.00 140.00  120
 21  \w   -130.00 -10.00   1.00    4.00    -- -100.00  72.00 210.00  120
 22  \w   -130.00 -10.00   1.00    4.00    -- -100.00  72.00 280.00  120
 23  \w   -190.00 -10.00   1.00    4.00    -- -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  0.1204
_diffrn_reflns_av_unetI/netI     0.0639
_diffrn_reflns_Laue_measured_fraction_full 0.962
_diffrn_reflns_Laue_measured_fraction_max 0.934
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            23733
_diffrn_reflns_point_group_measured_fraction_full 0.962
_diffrn_reflns_point_group_measured_fraction_max 0.934
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.787
_diffrn_reflns_theta_min         2.256
_diffrn_source                   MicroMax003_Cu
_diffrn_source_current           0.6
_diffrn_source_power             0.0
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    4.684
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.44547
_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    1.461
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             532
_exptl_crystal_size_max          0.410
_exptl_crystal_size_mid          0.380
_exptl_crystal_size_min          0.330
_refine_diff_density_max         0.701
_refine_diff_density_min         -0.532
_refine_diff_density_rms         0.122
_refine_ls_extinction_coef       0.0155(17)
_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   1.047
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     296
_refine_ls_number_reflns         4386
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0836
_refine_ls_R_factor_gt           0.0726
_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^)+(0.1222P)^2^+0.5265P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1881
_refine_ls_wR_factor_ref         0.2029
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3561
_reflns_number_total             4386
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ce00948c2.cif
_cod_data_source_block           TCZ-FUMH1
_cod_depositor_comments
'Adding full bibliography for 7247709--7247724.cif.'
_cod_database_code               7247722
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.250
_shelx_estimated_absorpt_t_max   0.307
_shelx_res_checksum              6764