The unexpected discovery of the ninth polymorph of tolfenamic acid
Sacchi, Pietro; Reutzel-Edens, Susan M.; Cruz-Cabeza, Aurora J.; CrystEngComm 23 (2021) 3636–3647; doi:10.1039/D1CE00343G

data_7242687
_publ_section_title
;
 The unexpected discovery of the ninth polymorph of tolfenamic acid
;
_journal_issue                   20
_journal_name_full               CrystEngComm
_journal_page_first              3636
_journal_page_last               3647
_journal_paper_doi               10.1039/D1CE00343G
_journal_volume                  23
_journal_year                    2021
_chemical_formula_moiety         'C14 H12 Cl N O2'
_chemical_formula_sum            'C14 H12 Cl N O2'
_chemical_formula_weight         261.70
_chemical_name_common
'Clotam, Tolfedine,2-[(3-Chloro-2-methylphenyl)amino]benzoic Acid'
_chemical_name_systematic        'tolfenamic acid'
_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
_audit_creation_date             2021-02-09
_audit_creation_method
;
Olex2 1.3
(compiled Nov 21 2019 18:26:39 for OlexSys, GUI svn.r6003)
;
_audit_update_record
;
2021-03-10 deposited with the CCDC.	2021-04-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.399(9)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.5841(11)
_cell_length_b                   7.8503(6)
_cell_length_c                   14.9718(13)
_cell_measurement_reflns_used    3219
_cell_measurement_temperature    293.3(7)
_cell_measurement_theta_max      23.2580
_cell_measurement_theta_min      3.4060
_cell_volume                     1219.44(19)
_computing_cell_refinement       'CrysAlisPro 1.171.40.71a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.71a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.71a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      293.3(7)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1636
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.911
_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    -42.00  39.00   1.00   50.00    --  -10.25  77.00  30.00   81
  2  \w    -39.00  21.00   1.00   50.00    --  -10.25 -77.00 -90.00   60
  3  \w    -42.00  39.00   1.00   50.00    --  -10.25  77.00 -90.00   81
  4  \w    -39.00  41.00   1.00   50.00    --    9.93 -77.00-180.00   80
  5  \w    -80.00  16.00   1.00   50.00    --  -10.25 -57.00-150.00   96
  6  \w    -80.00 -55.00   1.00   50.00    --  -10.25 -57.00  30.00   25
  7  \w    -39.00  11.00   1.00   50.00    --  -10.25 -77.00  90.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0162852000
_diffrn_orient_matrix_UB_12      0.0139249000
_diffrn_orient_matrix_UB_13      -0.0477113000
_diffrn_orient_matrix_UB_21      0.0615698000
_diffrn_orient_matrix_UB_22      -0.0301891000
_diffrn_orient_matrix_UB_23      -0.0045134000
_diffrn_orient_matrix_UB_31      -0.0248245000
_diffrn_orient_matrix_UB_32      -0.0840310000
_diffrn_orient_matrix_UB_33      -0.0062794000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0724
_diffrn_reflns_av_unetI/netI     0.0746
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.911
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            16842
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.911
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.577
_diffrn_reflns_theta_min         2.776
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.305
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.97839
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.71a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.425
_exptl_crystal_description       block
_exptl_crystal_F_000             544
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: 2-propanol'
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.240
_refine_diff_density_min         -0.240
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         3119
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.1288
_refine_ls_R_factor_gt           0.0577
_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^)+(0.0379P)^2^+0.1049P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0992
_refine_ls_wR_factor_ref         0.1247
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1692
_reflns_number_total             3119
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ce00343g2.cif
_cod_data_source_block           oacc123
_cod_depositor_comments          'Adding full bibliography for 7242687.cif.'
_cod_database_code               7242687
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.976
_shelx_estimated_absorpt_t_min   0.933
_reflns_odcompleteness_completeness 99.81
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
3.a Aromatic/amide H refined with riding coordinates:
 C3(H2), C4(H3), C5(H4), C6(H5), C9(H7), C10(H8), C11(H9)
3.b Idealised Me refined as rotating group:
 C14(H10,H11,H12)
;
_shelx_res_checksum              83438
_olex2_date_sample_data_collection 2020-03-16
_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 1.028
_oxdiff_exptl_absorpt_empirical_full_min 0.964