New approach for preparation of metastable phenylbutazone polymorphs
Gabdulkhaev, Mukhammet N.; Simdyanova, Anastasia V.; Bolmatenkov, Dmitrii N.; Gubaidullin, Aidar T.; Mukhametzyanov, Timur A.; Ziganshin, Marat A.; Gorbatchuk, Valery V.; CrystEngComm 27 (2025) 2490–2501; doi:10.1039/D5CE00094G

data_7250094
_publ_section_title
;
 New approach for preparation of metastable phenylbutazone polymorphs
;
_journal_issue                   16
_journal_name_full               CrystEngComm
_journal_page_first              2490
_journal_page_last               2501
_journal_paper_doi               10.1039/D5CE00094G
_journal_volume                  27
_journal_year                    2025
_chemical_formula_moiety         'C19 H20 N2 O3'
_chemical_formula_sum            'C19 H20 N2 O3'
_chemical_formula_weight         324.37
_chemical_name_systematic        4-hydroxy-phenylbutazone
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2024-08-22 deposited with the CCDC.	2025-03-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.782(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.2150(10)
_cell_length_b                   5.9581(4)
_cell_length_c                   17.4194(12)
_cell_measurement_reflns_used    9906
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.25
_cell_measurement_theta_min      2.34
_cell_volume                     1680.92(19)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'APEX3 v2019.11-0 (Bruker AXS)'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'area detector PHOTON III'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker D8 QUEST'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  'multilayer optics'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0785
_diffrn_reflns_av_unetI/netI     0.0399
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            41545
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.286
_diffrn_reflns_theta_min         2.515
_diffrn_source                   'microfocus I\mS DIAMOND Mo X-ray tube'
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_correction_T_min  0.6338
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 G.M. Sheldrick (1998a). SADABS v.2.01, Bruker.
 Siemens Area Detector Absorption Correction Program.
 Bruker AXS. Madison. Wisconsin. USA
  Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
  SADABS-2016/2, J. Appl. Cryst. 48 (2015) 3-10. 
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.282
_exptl_crystal_description       prism
_exptl_crystal_F_000             688
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: crystallization from acetonitrile at room temperature during 3 weeks'
_exptl_crystal_size_max          0.261
_exptl_crystal_size_mid          0.253
_exptl_crystal_size_min          0.223
_refine_diff_density_max         0.430
_refine_diff_density_min         -0.192
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     222
_refine_ls_number_reflns         4558
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.016
_refine_ls_R_factor_all          0.0555
_refine_ls_R_factor_gt           0.0441
_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^)+(0.0608P)^2^+0.5625P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1138
_refine_ls_wR_factor_ref         0.1223
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3731
_reflns_number_total             4558
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ce00094g2.cif
_cod_data_source_block           shelx_CCDC1
_cod_depositor_comments
'Adding full bibliography for 7250093--7250094.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7250094
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.978
_shelx_estimated_absorpt_t_max   0.981
_shelx_res_checksum              26297