Isomorphism: `molecular similarity to crystal structure similarity' in multicomponent forms of analgesic drugs tolfenamic and mefenamic acid
Ranjan, Subham; Devarapalli, Ramesh; Kundu, Sudeshna; Saha, Subhankar; Deolka, Shubham; Vangala, Venu R.; Reddy, C. Malla; IUCrJ 7 (2020) 173–183; doi:10.1107/S205225251901604X

data_1557484
_publ_section_title
;
 Isomorphism: `molecular similarity to crystal structure similarity' in
 multicomponent forms of analgesic drugs tolfenamic and mefenamic acid
;
_journal_issue                   2
_journal_name_full               IUCrJ
_journal_page_first              173
_journal_page_last               183
_journal_paper_doi               10.1107/S205225251901604X
_journal_volume                  7
_journal_year                    2020
_chemical_formula_moiety         'C14 H12 Cl N O2'
_chemical_formula_sum            'C14 H12 Cl N O2'
_chemical_formula_weight         261.70
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2019-10-09
_audit_creation_method
;
Olex2 1.3
(compiled 2019.09.11 svn.r3662 for OlexSys, GUI svn.r5938)
;
_cell_angle_alpha                77.167(4)
_cell_angle_beta                 79.908(3)
_cell_angle_gamma                65.487(4)
_cell_formula_units_Z            2
_cell_length_a                   6.7049(3)
_cell_length_b                   7.2778(3)
_cell_length_c                   14.1630(6)
_cell_measurement_reflns_used    6423
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      26.4300
_cell_measurement_theta_min      2.9290
_cell_volume                     610.42(5)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_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    'SHELXT 2014/4 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 7.9580
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.995
_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     -9.00 105.00   1.00   10.00    --   29.32  57.00 120.00  114
  2  \w     35.00 124.00   1.00   10.00    --   29.32 178.00  30.00   89
  3  \w    -14.00 114.00   1.00   10.00    --   29.32  77.00-150.00  128
  4  \w    -14.00 114.00   1.00   10.00    --   29.32  77.00 -30.00  128
  5  \w    -55.00  73.00   1.00   10.00    --   29.32 -77.00  90.00  128
  6  \w     35.00 124.00   1.00   10.00    --   29.32 178.00 120.00   89
  7  \w    -31.00  26.00   1.00   10.00    --  -23.50 -90.00 -53.00   57
  8  \w    -55.00 116.00   1.00   10.00    --   29.32  19.00-180.00  171
  9  \w     -9.00 105.00   1.00   10.00    --   29.32  57.00 -90.00  114
 10  \w    -47.00  67.00   1.00   10.00    --   29.32 -57.00 -90.00  114
 11  \w    -52.00  85.00   1.00   10.00    --   29.32 -38.00 120.00  137
 12  \w     -9.00  21.00   1.00   10.00    --   29.32  57.00-150.00   30
 13  \w    -14.00 114.00   1.00   10.00    --   29.32  77.00  90.00  128
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0569663000
_diffrn_orient_matrix_UB_12      -0.0103875000
_diffrn_orient_matrix_UB_13      -0.0469491000
_diffrn_orient_matrix_UB_21      0.0084794000
_diffrn_orient_matrix_UB_22      0.0953342000
_diffrn_orient_matrix_UB_23      -0.0036364000
_diffrn_orient_matrix_UB_31      0.1015917000
_diffrn_orient_matrix_UB_32      -0.0510437000
_diffrn_orient_matrix_UB_33      0.0210758000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0314
_diffrn_reflns_av_unetI/netI     0.0198
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            11414
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.027
_diffrn_reflns_theta_max         25.027
_diffrn_reflns_theta_min         2.963
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.305
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.37641
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.424
_exptl_crystal_description       plate
_exptl_crystal_F_000             272
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.406
_refine_diff_density_min         -1.389
_refine_diff_density_rms         0.096
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     168
_refine_ls_number_reflns         2133
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0842
_refine_ls_R_factor_gt           0.0792
_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^)+(0.1132P)^2^+1.7122P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2157
_refine_ls_wR_factor_ref         0.2204
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1931
_reflns_number_total             2133
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ed5019.cif
_cod_data_source_block           tfa_form-vi
_cod_database_code               1557484
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H N O Cl'
_shelx_estimated_absorpt_t_max   0.942
_shelx_estimated_absorpt_t_min   0.838
_reflns_odcompleteness_completeness 92.81
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.04
_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. Restrained distances
 N1-H1A
 0.87 with sigma of 0.02
3.a Fixed occupancy and ADP/Uiso:
 H1A
3.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C11(H11), C12(H12), C13(H13)
3.c Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C)
3.d Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_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 1.567
_oxdiff_exptl_absorpt_empirical_full_min 0.366