Crystal structure of febuxostat marketed polymorph determined by electron diffraction and reinforced by X-ray crystallography
Ungur, Doriana T.; Lanza, Arianna; Stam, Danny; Guguta, Carmen; Iordache, Coca; Fruth, Victor; Santiso-Quinones, Gustavo; Pop, Mihaela M.; CrystEngComm 26 (2024) 4295–4304; doi:10.1039/D4CE00518J

data_7249053
_publ_section_title
;
 Crystal structure of febuxostat marketed polymorph determined by electron
 diffraction and reinforced by X-ray crystallography
;
_journal_issue                   32
_journal_name_full               CrystEngComm
_journal_page_first              4295
_journal_page_last               4304
_journal_paper_doi               10.1039/D4CE00518J
_journal_volume                  26
_journal_year                    2024
_chemical_formula_moiety         'C16 H16 N2 O3 S'
_chemical_formula_sum            'C16 H16 N2 O3 S'
_chemical_formula_weight         316.37
_chemical_name_common            Febuxostat
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2024-05-06
_audit_creation_method
;
Olex2 1.2
(compiled Apr  3 2018 11:26:26 for OlexSys, GUI svn.r5486)
;
_audit_update_record
;
2024-05-22 deposited with the CCDC.	2024-07-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   8.9872(6)
_cell_length_b                   13.7547(9)
_cell_length_c                   26.5649(17)
_cell_measurement_reflns_used    1618
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      64.9110
_cell_measurement_theta_min      3.3160
_cell_volume                     3283.9(4)
_computing_cell_refinement       'CrysAlisPro 1.171.41.16a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.41.16a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.41.16a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.4335
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.982
_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     32.00  64.00   2.00    7.63    --    0.00  57.00  90.00   16
  2  \w     -2.00  26.00   2.00    7.63    --    0.00  57.00  90.00   14
  3  \w    -66.00 -24.00   2.00    7.63    --    0.00 -57.00  30.00   21
  4  \w     77.00 113.00   2.00   30.55    --   54.00  57.00  90.00   18
  5  \w     70.00  96.00   2.00   30.55    --   54.00  57.00 -90.00   13
  6  \w     26.00 112.00   2.00   30.55    --   54.00-126.00-180.00   43
  7  \w     33.00  61.00   2.00   30.55    --   54.00  57.00  30.00   14
  8  \w     73.00 123.00   2.00   30.55    --   54.00  57.00  30.00   25
  9  \w     86.00 178.00   2.00   30.55    --  108.00  50.00 -30.00   46
 10  \w     49.00  87.00   2.00   30.55    --  108.00 -92.00  60.00   19
 11  \w     72.00 100.00   2.00   30.55    --  108.00 -92.00 -60.00   14
 12  \w     36.00 112.00   2.00   30.55    --  108.00-112.00-120.00   38
 13  \w     93.00 159.00   2.00   30.55    --  108.00  50.00 -90.00   33
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0415
_diffrn_reflns_av_unetI/netI     0.0672
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            7338
_diffrn_reflns_point_group_measured_fraction_full 0.762
_diffrn_reflns_point_group_measured_fraction_max 0.742
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.496
_diffrn_reflns_theta_min         3.327
_exptl_absorpt_coefficient_mu    1.870
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.18797
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.16a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.280
_exptl_crystal_description       needle
_exptl_crystal_F_000             1328
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.318
_refine_diff_density_min         -0.454
_refine_diff_density_rms         0.054
_refine_ls_abs_structure_details
;
 Flack x determined using 758 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.34(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     405
_refine_ls_number_reflns         4652
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.006
_refine_ls_R_factor_all          0.1005
_refine_ls_R_factor_gt           0.0629
_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^)+(0.0705P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1407
_refine_ls_wR_factor_ref         0.1689
_reflns_Friedel_coverage         0.477
_reflns_Friedel_fraction_full    0.514
_reflns_Friedel_fraction_max     0.490
_reflns_number_gt                2985
_reflns_number_total             4652
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ce00518j3.cif
_cod_data_source_block           Febuxostat-ortho-SC
_cod_depositor_comments          'Adding full bibliography for 7249053.cif.'
_cod_database_code               7249053
_shelx_shelxl_version_number     2014/7
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C13(H13), C13A(H13A)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C7A(H7AA,H7AB)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C9(H9), C4(H4), C4A(H4A), C2A(H2A), C9A(H9A)
2.d Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C15(H15A,H15B,H15C), C16(H16A,H16B,H16C), C15A(H15D,H15E,
 H15F), C14A(H14D,H14E,H14F), C16A(H16D,H16E,H16F)
2.e Idealised tetrahedral OH refined as rotating group:
 O1(H1), O1A(H1A)
;
_shelx_res_checksum              39006
_shelx_hkl_checksum              25310
_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
;