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_7250118
_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         'H O4 S, C13 H9 N6'
_chemical_formula_sum            'C13 H10 N6 O4 S'
_chemical_formula_weight         346.33
_chemical_melting_point          507.55
_chemical_name_systematic        'FYX-H2SO4 II'
_space_group_crystal_system      orthorhombic
_space_group_IT_number           34
_space_group_name_Hall           'P 2 -2n'
_space_group_name_H-M_alt        'P n n 2'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_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                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.6047(13)
_cell_length_b                   25.471(3)
_cell_length_c                   4.4874(5)
_cell_measurement_reflns_used    9975
_cell_measurement_temperature    150.00
_cell_measurement_theta_max      57.127
_cell_measurement_theta_min      4.295
_cell_volume                     1440.7(3)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_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    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      150.00
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_reflns_av_R_equivalents  0.0705
_diffrn_reflns_av_unetI/netI     0.0461
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_l_max       4
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_number            15054
_diffrn_reflns_point_group_measured_fraction_full 0.938
_diffrn_reflns_point_group_measured_fraction_max 0.925
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         57.093
_diffrn_reflns_theta_min         3.404
_diffrn_source_current           2.86
_diffrn_source_power             0.1997996
_diffrn_source_voltage           69.86
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.520
_exptl_absorpt_correction_T_max  0.7512
_exptl_absorpt_correction_T_min  0.5352
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1681 before and 0.0768 after correction.
The Ratio of minimum to maximum transmission is 0.7125.
The \l/2 correction factor is Not present.
;
_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    1.597
_exptl_crystal_description       needle
_exptl_crystal_F_000             712
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: methyl alcohol'
_exptl_crystal_size_max          0.9
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.232
_refine_diff_density_min         -0.474
_refine_diff_density_rms         0.056
_refine_ls_abs_structure_details
;
 Flack x determined using 966 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.057(14)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     221
_refine_ls_number_reflns         2754
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0372
_refine_ls_R_factor_gt           0.0347
_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^)+(0.0454P)^2^+0.4682P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0880
_refine_ls_wR_factor_ref         0.0896
_reflns_Friedel_coverage         0.646
_reflns_Friedel_fraction_full    0.861
_reflns_Friedel_fraction_max     0.837
_reflns_number_gt                2613
_reflns_number_total             2754
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ce00073d2.cif
_cod_data_source_block           11
_cod_depositor_comments
'Adding full bibliography for 7250115--7250119.cif.'
_cod_database_code               7250118
_shelx_shelxl_version_number     2018/3
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N3(H6), N1(H1), C12(H9), C9(H7), C10(H8), C4(H4), C2(H3), C5(H5), C1(H2)
;
_olex2_submission_special_instructions 'No special instructions were received'