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_7250117
_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         'C13 H8 N6'
_chemical_formula_sum            'C13 H8 N6'
_chemical_formula_weight         248.25
_chemical_name_systematic        'FYX I'
_chemical_properties_physical    Moisture-sensitive
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_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
;
2024-11-25 deposited with the CCDC.	2025-03-17 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.377(13)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   3.8498(12)
_cell_length_b                   12.368(3)
_cell_length_c                   12.116(4)
_cell_measurement_reflns_used    2114
_cell_measurement_temperature    150.00
_cell_measurement_theta_max      54.938
_cell_measurement_theta_min      3.196
_cell_volume                     573.3(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 0.978
_diffrn_measured_fraction_theta_max 0.965
_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  0.0615
_diffrn_reflns_av_unetI/netI     0.0840
_diffrn_reflns_Laue_measured_fraction_full 0.978
_diffrn_reflns_Laue_measured_fraction_max 0.965
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            3748
_diffrn_reflns_point_group_measured_fraction_full 0.826
_diffrn_reflns_point_group_measured_fraction_max 0.808
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         54.954
_diffrn_reflns_theta_min         3.109
_diffrn_source_current           2.86
_diffrn_source_power             0.19977099999999998
_diffrn_source_voltage           69.85
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.491
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'dull light colourless'
_exptl_crystal_colour_lustre     dull
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.438
_exptl_crystal_description       block
_exptl_crystal_F_000             256
_exptl_crystal_preparation       1
_exptl_crystal_recrystallization_method 1
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.5
_refine_diff_density_max         0.391
_refine_diff_density_min         -0.315
_refine_diff_density_rms         0.080
_refine_ls_abs_structure_details
;
 Flack x determined using 483 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.9(7)
_refine_ls_extinction_coef       0.033(10)
_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   1.149
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     177
_refine_ls_number_reflns         1771
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.149
_refine_ls_R_factor_all          0.0873
_refine_ls_R_factor_gt           0.0748
_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^)+(0.0889P)^2^+0.3866P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1896
_refine_ls_wR_factor_ref         0.1979
_reflns_Friedel_coverage         0.594
_reflns_Friedel_fraction_full    0.659
_reflns_Friedel_fraction_max     0.633
_reflns_number_gt                1499
_reflns_number_total             1771
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ce00073d2.cif
_cod_data_source_block           150k
_cod_depositor_comments
'Adding full bibliography for 7250115--7250119.cif.'
_cod_database_code               7250117
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.791
_shelx_estimated_absorpt_t_min   0.791
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.9960(19)
 0.0040(19)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
3.a Aromatic/amide H refined with riding coordinates:
 C9(H6), C10(H7), C12(H8), C4(H3), C5(H4), C1(H1), C2(H2)
;
_olex2_exptl_crystal_mounting_method 1
_olex2_submission_special_instructions 'No special instructions were received'