#------------------------------------------------------------------------------
#$Date: 2024-01-06 10:01:35 +0200 (Sat, 06 Jan 2024) $
#$Revision: 288801 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/77/7247713.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7247713
loop_
_publ_author_name
'Madhesiya, Avinash'
'Dash, Sibananda G.'
'Gupta, Princi'
'Akhir, Abdul'
'Saxena, Deepanshi'
'Maitra, Rahul'
'Chopra, Sidharth'
'Thakur, Tejender S.'
_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, 0.5(C2 H2 O4), 0.5(C2 O4)'
_chemical_formula_sum            'C18 H15 Cl3 N2 O5 S'
_chemical_formula_weight         477.73
_chemical_name_common
'Tioconazole-oxalate-oxalic acid  (1:0.5:0.5)salt 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-2018/3
_audit_update_record
;
2023-07-31 deposited with the CCDC.	2023-11-14 downloaded from the CCDC.
;
_cell_angle_alpha                112.364(4)
_cell_angle_beta                 105.711(2)
_cell_angle_gamma                96.357(2)
_cell_formula_units_Z            2
_cell_length_a                   10.2522(2)
_cell_length_b                   10.7638(4)
_cell_length_c                   11.0528(4)
_cell_measurement_reflns_used    12802
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      72.4630
_cell_measurement_theta_min      4.5780
_cell_volume                     1054.06(7)
_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 0.983
_diffrn_measured_fraction_theta_max 0.962
_diffrn_measurement_device
;
AFC12 (Right): Kappa 3 circle
;
_diffrn_measurement_device_type
;
Rigaku Saturn724+ (4x4 bin mode)
;
_diffrn_measurement_method       'profile data from ω-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  0.1141
_diffrn_reflns_av_unetI/netI     0.0550
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.962
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            21579
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.962
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.756
_diffrn_reflns_theta_min         4.576
_diffrn_source                   MicroMax003_Cu
_diffrn_source_current           0.6
_diffrn_source_power             0.0
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    5.158
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.19346
_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    1.505
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             488
_exptl_crystal_size_max          0.570
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.120
_refine_diff_density_max         0.930
_refine_diff_density_min         -0.669
_refine_diff_density_rms         0.119
_refine_ls_extinction_coef       0.023(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         4031
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0990
_refine_ls_R_factor_gt           0.0918
_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/[σ²(Fo²)+(0.1552P)²+1.3541P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2553
_refine_ls_wR_factor_ref         0.2641
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3495
_reflns_number_total             4031
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3ce00948c2.cif
_cod_data_source_block           TCZ-OXAC
_cod_depositor_comments
'Adding full bibliography for 7247709--7247724.cif.'
_cod_database_code               7247713
_shelx_shelxl_version_number     2018/3
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.157
_shelx_estimated_absorpt_t_max   0.577
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.1030(4) 0.2158(4) 0.7022(4) 0.0468(8) Uani 1 1 d . . . . .
C2 C 0.0010(4) 0.1781(4) 0.5752(5) 0.0576(10) Uani 1 1 d . . . . .
C3 C -0.1407(5) 0.1410(5) 0.5551(6) 0.0722(15) Uani 1 1 d . . . . .
H3 H -0.208455 0.118657 0.469776 0.087 Uiso 1 1 calc R U . . .
C4 C -0.1770(5) 0.1386(5) 0.6651(6) 0.0711(13) Uani 1 1 d . . . . .
C5 C -0.0810(5) 0.1741(5) 0.7918(6) 0.0659(12) Uani 1 1 d . . . . .
H5 H -0.108005 0.172368 0.865028 0.079 Uiso 1 1 calc R U . . .
C6 C 0.0600(4) 0.2136(4) 0.8091(5) 0.0538(10) Uani 1 1 d . . . . .
H6 H 0.126891 0.239161 0.895780 0.065 Uiso 1 1 calc R U . . .
C7 C 0.2575(3) 0.2580(4) 0.7255(4) 0.0430(8) Uani 1 1 d . . . . .
H7 H 0.278931 0.191200 0.648513 0.052 Uiso 1 1 calc R U . . .
C8 C 0.2993(3) 0.4021(4) 0.7342(4) 0.0422(8) Uani 1 1 d . . . . .
H8A H 0.231685 0.411811 0.659829 0.051 Uiso 1 1 calc R U . . .
H8B H 0.299945 0.470885 0.822182 0.051 Uiso 1 1 calc R U . . .
C9 C 0.5600(4) 0.4641(5) 0.8224(4) 0.0519(9) Uani 1 1 d . . . . .
H9 H 0.572798 0.487505 0.915671 0.062 Uiso 1 1 calc R U . . .
C10 C 0.6026(5) 0.4252(6) 0.6324(5) 0.0687(13) Uani 1 1 d . . . . .
H10 H 0.649913 0.416458 0.569799 0.082 Uiso 1 1 calc R U . . .
C11 C 0.4640(4) 0.4008(6) 0.6022(5) 0.0649(13) Uani 1 1 d . . . . .
H11 H 0.397393 0.372290 0.514728 0.078 Uiso 1 1 calc R U . . .
C12 C 0.3606(4) 0.1316(4) 0.8487(5) 0.0549(10) Uani 1 1 d . . . . .
H12A H 0.408265 0.089720 0.784337 0.066 Uiso 1 1 calc R U . . .
H12B H 0.270470 0.069659 0.819360 0.066 Uiso 1 1 calc R U . . .
C13 C 0.3962(6) 0.1442(6) 1.0901(6) 0.0718(13) Uani 1 1 d . . . . .
C14 C 0.4451(5) 0.1591(4) 0.9926(5) 0.0546(10) Uani 1 1 d . . . . .
C15 C 0.5916(5) 0.2146(5) 1.0508(6) 0.0674(12) Uani 1 1 d . . . . .
H15 H 0.645470 0.232738 1.001208 0.081 Uiso 1 1 calc R U . . .
C16 C 0.6446(6) 0.2384(6) 1.1858(6) 0.0857(18) Uani 1 1 d . . . . .
H16 H 0.738936 0.274486 1.238628 0.103 Uiso 1 1 calc R U . . .
C17 C 0.9614(3) 0.5007(4) 0.5516(4) 0.0410(8) Uani 1 1 d . . . . .
C18 C 1.0334(3) 0.5207(4) 0.9528(3) 0.0396(8) Uani 1 1 d . . . . .
N1 N 0.4382(3) 0.4254(3) 0.7228(3) 0.0402(7) Uani 1 1 d . . . . .
N2 N 0.6606(3) 0.4646(4) 0.7698(4) 0.0536(9) Uani 1 1 d . . . . .
O1 O 0.3438(2) 0.2637(3) 0.8526(3) 0.0445(6) Uani 1 1 d . . . . .
O2 O 0.8367(3) 0.4629(4) 0.5117(3) 0.0705(10) Uani 1 1 d . . . . .
O3 O 1.0457(3) 0.5446(4) 0.6766(3) 0.0543(8) Uani 1 1 d . . . . .
O4 O 0.9446(2) 0.5296(3) 0.8515(3) 0.0503(7) Uani 1 1 d . . . . .
O5 O 1.1593(2) 0.5430(3) 0.9802(3) 0.0511(7) Uani 1 1 d . . . . .
S2 S 0.5228(2) 0.19614(18) 1.24859(15) 0.0920(6) Uani 1 1 d . . . . .
Cl1 Cl 0.04498(15) 0.17535(13) 0.43310(12) 0.0745(5) Uani 1 1 d . . . . .
Cl2 Cl -0.35295(14) 0.0862(2) 0.6386(3) 0.1249(8) Uani 1 1 d . . . . .
Cl3 Cl 0.2256(2) 0.0799(3) 1.0659(3) 0.1367(10) Uani 1 1 d . . . . .
H2N H 0.754(8) 0.472(8) 0.818(9) 0.12(3) Uiso 1 1 d . . . . .
H3O H 1.001(8) 0.534(8) 0.721(8) 0.11(2) Uiso 1 1 d . . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 C1 C2 117.4(4) . . ?
C6 C1 C7 120.3(3) . . ?
C2 C1 C7 122.3(4) . . ?
C1 C2 C3 121.9(5) . . ?
C1 C2 Cl1 120.9(3) . . ?
C3 C2 Cl1 117.2(4) . . ?
C4 C3 C2 117.9(5) . . ?
C4 C3 H3 121.0 . . ?
C2 C3 H3 121.0 . . ?
C5 C4 C3 122.5(4) . . ?
C5 C4 Cl2 119.4(4) . . ?
C3 C4 Cl2 118.1(4) . . ?
C4 C5 C6 118.1(5) . . ?
C4 C5 H5 121.0 . . ?
C6 C5 H5 121.0 . . ?
C1 C6 C5 122.1(4) . . ?
C1 C6 H6 118.9 . . ?
C5 C6 H6 118.9 . . ?
O1 C7 C1 112.5(3) . . ?
O1 C7 C8 105.1(3) . . ?
C1 C7 C8 112.2(3) . . ?
O1 C7 H7 109.0 . . ?
C1 C7 H7 109.0 . . ?
C8 C7 H7 109.0 . . ?
N1 C8 C7 110.3(3) . . ?
N1 C8 H8A 109.6 . . ?
C7 C8 H8A 109.6 . . ?
N1 C8 H8B 109.6 . . ?
C7 C8 H8B 109.6 . . ?
H8A C8 H8B 108.1 . . ?
N2 C9 N1 109.6(3) . . ?
N2 C9 H9 125.2 . . ?
N1 C9 H9 125.2 . . ?
C11 C10 N2 107.3(4) . . ?
C11 C10 H10 126.3 . . ?
N2 C10 H10 126.3 . . ?
C10 C11 N1 107.6(4) . . ?
C10 C11 H11 126.2 . . ?
N1 C11 H11 126.2 . . ?
O1 C12 C14 106.1(3) . . ?
O1 C12 H12A 110.5 . . ?
C14 C12 H12A 110.5 . . ?
O1 C12 H12B 110.5 . . ?
C14 C12 H12B 110.5 . . ?
H12A C12 H12B 108.7 . . ?
C14 C13 S2 113.8(4) . . ?
C14 C13 Cl3 126.0(4) . . ?
S2 C13 Cl3 120.1(3) . . ?
C13 C14 C15 109.8(4) . . ?
C13 C14 C12 126.6(4) . . ?
C15 C14 C12 123.5(4) . . ?
C16 C15 C14 112.9(5) . . ?
C16 C15 H15 123.5 . . ?
C14 C15 H15 123.5 . . ?
C15 C16 S2 113.2(4) . . ?
C15 C16 H16 123.4 . . ?
S2 C16 H16 123.4 . . ?
O2 C17 O3 127.1(3) . . ?
O2 C17 C17 120.6(4) . 2_766 ?
O3 C17 C17 112.3(3) . 2_766 ?
O5 C18 O4 126.3(3) . . ?
O5 C18 C18 120.0(4) . 2_767 ?
O4 C18 C18 113.7(3) . 2_767 ?
C9 N1 C11 107.2(3) . . ?
C9 N1 C8 127.5(3) . . ?
C11 N1 C8 125.2(3) . . ?
C9 N2 C10 108.4(3) . . ?
C9 N2 H2N 124(5) . . ?
C10 N2 H2N 127(5) . . ?
C7 O1 C12 114.6(3) . . ?
C17 O3 H3O 107(5) . . ?
C16 S2 C13 90.2(3) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C6 1.376(6) . ?
C1 C2 1.380(6) . ?
C1 C7 1.521(5) . ?
C2 C3 1.396(6) . ?
C2 Cl1 1.738(5) . ?
C3 C4 1.372(8) . ?
C3 H3 0.9300 . ?
C4 C5 1.356(8) . ?
C4 Cl2 1.738(5) . ?
C5 C6 1.399(6) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 O1 1.417(4) . ?
C7 C8 1.522(5) . ?
C7 H7 0.9800 . ?
C8 N1 1.466(4) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 N2 1.314(5) . ?
C9 N1 1.318(5) . ?
C9 H9 0.9300 . ?
C10 C11 1.339(6) . ?
C10 N2 1.344(6) . ?
C10 H10 0.9300 . ?
C11 N1 1.361(5) . ?
C11 H11 0.9300 . ?
C12 O1 1.437(5) . ?
C12 C14 1.486(6) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.358(7) . ?
C13 S2 1.711(6) . ?
C13 Cl3 1.718(6) . ?
C14 C15 1.418(6) . ?
C15 C16 1.352(8) . ?
C15 H15 0.9300 . ?
C16 S2 1.684(8) . ?
C16 H16 0.9300 . ?
C17 O2 1.199(4) . ?
C17 O3 1.283(4) . ?
C17 C17 1.552(6) 2_766 ?
C18 O5 1.216(4) . ?
C18 O4 1.281(4) . ?
C18 C18 1.559(6) 2_767 ?
N2 H2N 0.94(8) . ?
O3 H3O 0.79(8) . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 0.9(6) . . . . ?
C7 C1 C2 C3 -179.3(4) . . . . ?
C6 C1 C2 Cl1 -179.1(3) . . . . ?
C7 C1 C2 Cl1 0.7(6) . . . . ?
C1 C2 C3 C4 -2.0(7) . . . . ?
Cl1 C2 C3 C4 178.0(4) . . . . ?
C2 C3 C4 C5 1.8(8) . . . . ?
C2 C3 C4 Cl2 -177.7(4) . . . . ?
C3 C4 C5 C6 -0.5(7) . . . . ?
Cl2 C4 C5 C6 178.9(4) . . . . ?
C2 C1 C6 C5 0.4(6) . . . . ?
C7 C1 C6 C5 -179.4(4) . . . . ?
C4 C5 C6 C1 -0.7(7) . . . . ?
C6 C1 C7 O1 12.4(5) . . . . ?
C2 C1 C7 O1 -167.4(3) . . . . ?
C6 C1 C7 C8 -105.9(4) . . . . ?
C2 C1 C7 C8 74.3(5) . . . . ?
O1 C7 C8 N1 71.1(3) . . . . ?
C1 C7 C8 N1 -166.3(3) . . . . ?
N2 C10 C11 N1 -0.2(6) . . . . ?
S2 C13 C14 C15 0.2(5) . . . . ?
Cl3 C13 C14 C15 -179.6(4) . . . . ?
S2 C13 C14 C12 -175.9(3) . . . . ?
Cl3 C13 C14 C12 4.2(8) . . . . ?
O1 C12 C14 C13 98.4(5) . . . . ?
O1 C12 C14 C15 -77.2(5) . . . . ?
C13 C14 C15 C16 -0.1(6) . . . . ?
C12 C14 C15 C16 176.2(4) . . . . ?
C14 C15 C16 S2 -0.1(6) . . . . ?
N2 C9 N1 C11 -0.1(5) . . . . ?
N2 C9 N1 C8 175.6(3) . . . . ?
C10 C11 N1 C9 0.2(6) . . . . ?
C10 C11 N1 C8 -175.7(4) . . . . ?
C7 C8 N1 C9 -82.5(5) . . . . ?
C7 C8 N1 C11 92.6(5) . . . . ?
N1 C9 N2 C10 0.0(5) . . . . ?
C11 C10 N2 C9 0.1(6) . . . . ?
C1 C7 O1 C12 79.4(4) . . . . ?
C8 C7 O1 C12 -158.2(3) . . . . ?
C14 C12 O1 C7 -176.1(3) . . . . ?
C15 C16 S2 C13 0.2(4) . . . . ?
C14 C13 S2 C16 -0.3(4) . . . . ?
Cl3 C13 S2 C16 179.6(4) . . . . ?
