Inorganic salts of topiroxostat: metastable tautomeric form and improved pharmaceutical performance
Li, Jiangying; Ma, Haowen; Shi, Xiaoju; Jiao, Ting; Wang, Lin; Nie, Meiling; Wang, Xiaojuan; Deng, Zongwu; Zhang, Hailu; CrystEngComm 27 (2025) 2534–2544; doi:10.1039/D5CE00073D

data_7250115
_publ_section_title
;
 Inorganic salts of topiroxostat: metastable tautomeric form and improved
 pharmaceutical performance
;
_journal_issue                   16
_journal_name_full               CrystEngComm
_journal_page_first              2534
_journal_page_last               2544
_journal_paper_doi               10.1039/D5CE00073D
_journal_volume                  27
_journal_year                    2025
_chemical_formula_moiety         'Cl, H2 O, C13 H9 N6'
_chemical_formula_sum            'C13 H11 Cl N6 O'
_chemical_formula_weight         302.73
_chemical_melting_point          579.35
_chemical_name_systematic        FYX-HCl-H2O
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_audit_creation_date             2024-11-14
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2024-11-14 deposited with the CCDC.	2025-03-17 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.559(8)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.8673(7)
_cell_length_b                   11.7052(11)
_cell_length_c                   17.4705(14)
_cell_measurement_reflns_used    2680
_cell_measurement_temperature    222.97(10)
_cell_measurement_theta_max      29.1690
_cell_measurement_theta_min      2.1040
_cell_volume                     1402.9(2)
_computing_cell_refinement       'CrysAlisPro 1.171.42.81a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.81a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.81a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      222.97(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4471
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.865
_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     24.00  51.00   1.00    1.00    --   12.72 -99.00 -90.00   27
  2  \w    -64.00  54.00   1.00    1.00    --   12.72 -19.00-180.00  118
  3  \w    -36.00  10.00   1.00    1.00    --  -13.50 -77.00   0.00   46
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0885910000
_diffrn_orient_matrix_UB_12      -0.0109226000
_diffrn_orient_matrix_UB_13      0.0211889000
_diffrn_orient_matrix_UB_21      0.0184490000
_diffrn_orient_matrix_UB_22      0.0595406000
_diffrn_orient_matrix_UB_23      0.0023124000
_diffrn_orient_matrix_UB_31      -0.0499679000
_diffrn_orient_matrix_UB_32      0.0027287000
_diffrn_orient_matrix_UB_33      0.0346136000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0517
_diffrn_reflns_av_unetI/netI     0.0794
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.865
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            7632
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.865
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.317
_diffrn_reflns_theta_min         2.095
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.281
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.68068
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.81a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.433
_exptl_crystal_description       needle
_exptl_crystal_F_000             624
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: H2O'
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.380
_refine_diff_density_min         -0.590
_refine_diff_density_rms         0.133
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         3647
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.1026
_refine_ls_R_factor_gt           0.0613
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0703P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1327
_refine_ls_wR_factor_ref         0.1703
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2286
_reflns_number_total             3647
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ce00073d2.cif
_cod_data_source_block           g231207b_auto
_cod_depositor_comments
'Adding full bibliography for 7250115--7250119.cif.'
_cod_database_code               7250115
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_usercomment     CHONF
_shelx_estimated_absorpt_t_max   0.921
_shelx_estimated_absorpt_t_min   0.896
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H,H) groups
2.a Free rotating group:
 O1(H1B,H1C)
2.b Aromatic/amide H refined with riding coordinates:
 C9(H9), C12(H12), C4(H4), C10(H10), C2(H2), C5(H5), C1(H1A)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.307
_oxdiff_exptl_absorpt_empirical_full_min 0.808