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_7247724
_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 H11 Cl3 N2 O S, C16 H13 Cl3 N2 O S, C8 H6 O4'
_chemical_formula_sum            'C40 H30 Cl6 N4 O6 S2'
_chemical_formula_weight         939.50
_chemical_name_common            'Tioconazole-Terepthalic 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   geom
_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                78.507(2)
_cell_angle_beta                 83.668(2)
_cell_angle_gamma                85.091(2)
_cell_formula_units_Z            2
_cell_length_a                   10.7290(3)
_cell_length_b                   12.8274(3)
_cell_length_c                   16.0617(5)
_cell_measurement_reflns_used    14208
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      72.0590
_cell_measurement_theta_min      2.7680
_cell_volume                     2148.36(10)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_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 0.959
_diffrn_measurement_details
;
scan:
	Number of images: 120
	           Slice: -130.0000 - -10.0000
	     Image width: 1.0000
	        Exp time: 4.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: -72.0000
	             Phi: 0.0000
	             XTD: 35.0004
	          2theta: -39.6388
scan:
	Number of images: 120
	           Slice: -130.0000 - -10.0000
	     Image width: 1.0000
	        Exp time: 4.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: -72.0000
	             Phi: 70.0000
	             XTD: 35.0004
	          2theta: -39.6388
scan:
	Number of images: 120
	           Slice: -130.0000 - -10.0000
	     Image width: 1.0000
	        Exp time: 4.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: -72.0000
	             Phi: 140.0000
	             XTD: 35.0004
	          2theta: -39.6388
scan:
	Number of images: 120
	           Slice: -130.0000 - -10.0000
	     Image width: 1.0000
	        Exp time: 4.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: -72.0000
	             Phi: 210.0000
	             XTD: 35.0004
	          2theta: -39.6388
scan:
	Number of images: 120
	           Slice: -130.0000 - -10.0000
	     Image width: 1.0000
	        Exp time: 4.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: -72.0000
	             Phi: 280.0000
	             XTD: 35.0004
	          2theta: -39.6388
scan:
	Number of images: 180
	           Slice: -130.0000 - 50.0000
	     Image width: 1.0000
	        Exp time: 4.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 0.0000
	             Phi: 0.0000
	             XTD: 35.0004
	          2theta: -39.6388
scan:
	Number of images: 120
	           Slice: -100.0000 - 20.0000
	     Image width: 1.0000
	        Exp time: 4.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 72.0000
	             Phi: 0.0000
	             XTD: 35.0004
	          2theta: -69.6388
scan:
	Number of images: 120
	           Slice: -100.0000 - 20.0000
	     Image width: 1.0000
	        Exp time: 4.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 72.0000
	             Phi: 70.0000
	             XTD: 35.0004
	          2theta: -69.6388
scan:
	Number of images: 120
	           Slice: -100.0000 - 20.0000
	     Image width: 1.0000
	        Exp time: 4.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 72.0000
	             Phi: 140.0000
	             XTD: 35.0004
	          2theta: -69.6388
scan:
	Number of images: 120
	           Slice: -100.0000 - 20.0000
	     Image width: 1.0000
	        Exp time: 4.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 72.0000
	             Phi: 210.0000
	             XTD: 35.0004
	          2theta: -69.6388
scan:
	Number of images: 120
	           Slice: -100.0000 - 20.0000
	     Image width: 1.0000
	        Exp time: 4.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 72.0000
	             Phi: 280.0000
	             XTD: 35.0004
	          2theta: -69.6388
scan:
	Number of images: 180
	           Slice: -160.0000 - 20.0000
	     Image width: 1.0000
	        Exp time: 4.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 0.0000
	             Phi: 0.0000
	             XTD: 35.0004
	          2theta: -69.6388
scan:
	Number of images: 120
	           Slice: -190.0000 - -70.0000
	     Image width: 1.0000
	        Exp time: 4.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: -72.0000
	             Phi: 0.0000
	             XTD: 35.0004
	          2theta: -99.6388
scan:
	Number of images: 120
	           Slice: -190.0000 - -70.0000
	     Image width: 1.0000
	        Exp time: 4.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: -72.0000
	             Phi: 70.0000
	             XTD: 35.0004
	          2theta: -99.6388
scan:
	Number of images: 120
	           Slice: -190.0000 - -70.0000
	     Image width: 1.0000
	        Exp time: 4.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: -72.0000
	             Phi: 140.0000
	             XTD: 35.0004
	          2theta: -99.6388
scan:
	Number of images: 120
	           Slice: -190.0000 - -70.0000
	     Image width: 1.0000
	        Exp time: 4.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: -72.0000
	             Phi: 210.0000
	             XTD: 35.0004
	          2theta: -99.6388
scan:
	Number of images: 120
	           Slice: -190.0000 - -70.0000
	     Image width: 1.0000
	        Exp time: 4.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: -72.0000
	             Phi: 280.0000
	             XTD: 35.0004
	          2theta: -99.6388
scan:
	Number of images: 120
	           Slice: -130.0000 - -10.0000
	     Image width: 1.0000
	        Exp time: 4.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 72.0000
	             Phi: 0.0000
	             XTD: 35.0004
	          2theta: -99.6388
scan:
	Number of images: 120
	           Slice: -130.0000 - -10.0000
	     Image width: 1.0000
	        Exp time: 4.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 72.0000
	             Phi: 70.0000
	             XTD: 35.0004
	          2theta: -99.6388
scan:
	Number of images: 120
	           Slice: -130.0000 - -10.0000
	     Image width: 1.0000
	        Exp time: 4.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 72.0000
	             Phi: 140.0000
	             XTD: 35.0004
	          2theta: -99.6388
scan:
	Number of images: 120
	           Slice: -130.0000 - -10.0000
	     Image width: 1.0000
	        Exp time: 4.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 72.0000
	             Phi: 210.0000
	             XTD: 35.0004
	          2theta: -99.6388
scan:
	Number of images: 120
	           Slice: -130.0000 - -10.0000
	     Image width: 1.0000
	        Exp time: 4.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 72.0000
	             Phi: 280.0000
	             XTD: 35.0004
	          2theta: -99.6388
scan:
	Number of images: 180
	           Slice: -190.0000 - -10.0000
	     Image width: 1.0000
	        Exp time: 4.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 0.0000
	             Phi: 0.0000
	             XTD: 35.0004
	          2theta: -99.6388

;
_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  0.1375
_diffrn_reflns_av_unetI/netI     0.0717
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.959
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            45274
_diffrn_reflns_point_group_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.959
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.864
_diffrn_reflns_theta_min         2.820
_diffrn_source                   MicroMax003_Cu
_diffrn_source_current           0.6
_diffrn_source_power             0.0
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    4.982
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.23093
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.452
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             960
_exptl_crystal_size_max          0.380
_exptl_crystal_size_mid          0.340
_exptl_crystal_size_min          0.110
_refine_diff_density_max         0.724
_refine_diff_density_min         -0.501
_refine_diff_density_rms         0.097
_refine_ls_extinction_coef       0.0065(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   1.187
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     543
_refine_ls_number_reflns         8208
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.187
_refine_ls_R_factor_all          0.1246
_refine_ls_R_factor_gt           0.0958
_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^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2802
_refine_ls_wR_factor_ref         0.3330
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5232
_reflns_number_total             8208
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ce00948c2.cif
_cod_data_source_block           TCA-TPTH1
_cod_depositor_comments
'Adding full bibliography for 7247709--7247724.cif.'
_cod_database_code               7247724
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.253
_shelx_estimated_absorpt_t_max   0.610
_shelx_res_checksum              61790