An investigation of the polymorphism of a potent nonsteroidal anti-inflammatory drug flunixin
Liu, Hao; Yang, Xing; Wu, Shanyu; Zhang, Mingtao; Parkin, Sean; Cao, Shuang; Li, Tonglei; Yu, Faquan; Long, Sihui; CrystEngComm 22 (2020) 448–457; doi:10.1039/C9CE01619H

data_7238041
_publ_section_title
;
 An investigation of the polymorphism of a potent nonsteroidal
 anti-inflammatory drug flunixin
;
_journal_issue                   3
_journal_name_full               CrystEngComm
_journal_page_first              448
_journal_page_last               457
_journal_paper_doi               10.1039/C9CE01619H
_journal_volume                  22
_journal_year                    2020
_chemical_formula_moiety         'C14 H11 F3 N2 O2'
_chemical_formula_sum            'C14 H11 F3 N2 O2'
_chemical_formula_weight         296.25
_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   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2018-03-22
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2019-10-04 deposited with the CCDC.	2019-11-22 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 102.1605(15)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.68546(13)
_cell_length_b                   14.1282(2)
_cell_length_c                   12.49862(17)
_cell_measurement_reflns_used    6019
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      66.4980
_cell_measurement_theta_min      4.7710
_cell_volume                     1326.67(4)
_computing_cell_refinement       'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_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                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4674
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.969
_diffrn_measured_fraction_theta_max 0.995
_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   -130.00 -57.00   1.00    1.00    --  -41.55-178.00 -60.00   73
  2  \w     17.00 116.00   1.00    1.00    --   41.55  38.00   0.00   99
  3  \w    -33.00  66.00   1.00    1.00    --   41.55 -38.00  60.00   99
  4  \w     67.00 166.00   1.00    1.00    --   92.50  45.00  90.00   99
  5  \w      9.00 130.00   1.00    1.00    --   92.50 -91.00  42.95  121
  6  \w     60.00 169.00   1.00    1.00    --   92.50  77.00  90.00  109
  7  \w     67.00 166.00   1.00    1.00    --   92.50  45.00  60.00   99
  8  \w      9.00 129.00   1.00    1.00    --   92.50 -89.00 -93.75  120
  9  \w     73.00 166.00   1.00    1.00    --   92.50 125.00   0.00   93
 10  \w     11.00 145.00   1.00    1.00    --   92.50 -15.00 -30.00  134
 11  \w     73.00 166.00   1.00    1.00    --   92.50 125.00-150.00   93
 12  \w     63.00 165.00   1.00    1.00    --   92.50  61.00 -30.00  102
 13  \w     10.00  84.00   1.00    1.00    --   92.50 -95.00-120.00   74
 14  \w   -114.00 -37.00   1.00    1.00    --  -41.55 -57.00-180.00   77
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0000374000
_diffrn_orient_matrix_UB_12      0.1036376000
_diffrn_orient_matrix_UB_13      -0.0384413000
_diffrn_orient_matrix_UB_21      0.0377950000
_diffrn_orient_matrix_UB_22      0.0333698000
_diffrn_orient_matrix_UB_23      0.1200471000
_diffrn_orient_matrix_UB_31      0.2014434000
_diffrn_orient_matrix_UB_32      -0.0062335000
_diffrn_orient_matrix_UB_33      0.0045361000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0204
_diffrn_reflns_av_unetI/netI     0.0123
_diffrn_reflns_Laue_measured_fraction_full 0.969
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            11795
_diffrn_reflns_point_group_measured_fraction_full 0.969
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         66.494
_diffrn_reflns_theta_min         4.785
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance Ultra (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.120
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.70413
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.32a (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.483
_exptl_crystal_description       block
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.220
_refine_diff_density_min         -0.176
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       0.0178(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     193
_refine_ls_number_reflns         2318
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0446
_refine_ls_R_factor_gt           0.0393
_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^)+(0.0554P)^2^+0.4247P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1012
_refine_ls_wR_factor_ref         0.1074
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2037
_reflns_number_total             2318
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9ce01619h2.cif
_cod_data_source_block           flunixin
_cod_depositor_comments
;Adding full bibliography for 7238040--7238041.cif.

 Adding full bibliography for 7238040--7238041.cif.
;
_cod_database_code               7238041
_shelxl_version_number           2013-2
_chemical_oxdiff_formula         'C1 H1 N1 O1 F1'
_reflns_odcompleteness_completeness 98.02
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N7(H7), C13(H13), C4(H4), C6(H6), C11(H11), C12(H12), C5(H5)
2.b Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C)
2.c Idealised tetrahedral OH refined as rotating group:
 O15(H15)
;
_olex2_date_sample_data_collection 2018-03-22
_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
;
_oxdiff_exptl_absorpt_empirical_full_max 1.509
_oxdiff_exptl_absorpt_empirical_full_min 0.828