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_7250093
_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 O2, C2 H3 N'
_chemical_formula_sum            'C21 H23 N3 O2'
_chemical_formula_weight         349.42
_chemical_name_systematic        'phenylbutazone solvate with acetonitrile'
_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   geom
_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                 93.907(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   17.9766(19)
_cell_length_b                   5.7375(5)
_cell_length_c                   18.7841(18)
_cell_measurement_reflns_used    4200
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      22.64
_cell_measurement_theta_min      2.27
_cell_volume                     1932.9(3)
_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      120(2)
_diffrn_detector                 'area detector PHOTON III'
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.990
_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  0.1163
_diffrn_reflns_av_unetI/netI     0.1041
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            40999
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.282
_diffrn_reflns_theta_min         1.517
_diffrn_source                   'microfocus I\mS DIAMOND Mo X-ray tube'
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  0.7459
_exptl_absorpt_correction_T_min  0.3405
_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    1.201
_exptl_crystal_description       plate
_exptl_crystal_F_000             744
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: acetonitrile, at 6 deg. C during 3-4 hours'
_exptl_crystal_size_max          0.620
_exptl_crystal_size_mid          0.204
_exptl_crystal_size_min          0.084
_refine_diff_density_max         0.423
_refine_diff_density_min         -0.353
_refine_diff_density_rms         0.081
_refine_ls_extinction_coef       0.024(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.145
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         4756
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.146
_refine_ls_R_factor_all          0.1794
_refine_ls_R_factor_gt           0.1394
_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^)+9.9714P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2782
_refine_ls_wR_factor_ref         0.2957
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3301
_reflns_number_total             4756
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ce00094g2.cif
_cod_data_source_block           shelx
_cod_depositor_comments
'Adding full bibliography for 7250093--7250094.cif.'
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7250093
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.953
_shelx_estimated_absorpt_t_max   0.993
_shelx_res_checksum              24788