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_1557482
_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 H11 Cl N O2, C7 H11 N2, H2 O'
_chemical_formula_sum            'C21 H24 Cl N3 O3'
_chemical_formula_weight         401.88
_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                101.784(6)
_cell_angle_beta                 98.374(6)
_cell_angle_gamma                90.687(6)
_cell_formula_units_Z            2
_cell_length_a                   7.7631(6)
_cell_length_b                   8.0250(6)
_cell_length_c                   16.2297(12)
_cell_measurement_reflns_used    2768
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      65.9260
_cell_measurement_theta_min      5.6170
_cell_volume                     978.32(13)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (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 0.982
_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    103.00 178.00   1.00    2.00    --  108.00 104.00  30.00   75
  2  \w    130.00 165.00   1.00    2.00    --  108.00 104.00  60.00   35
  3  \w    122.00 148.00   1.00    2.00    --   67.04 111.00  60.00   26
  4  \w    110.00 178.00   1.00    2.00    --  108.00 138.00  90.00   68
  5  \w    146.00 177.00   1.00    2.00    --  108.00  77.00 150.00   31
  6  \w    131.00 178.00   1.00    2.00    --  108.00 138.00 150.00   47
  7  \w    118.00 171.00   1.00    2.00    --  108.00 104.00 120.00   53
  8  \w    100.00 149.00   1.00    2.00    --   67.04 111.00 -30.00   49
  9  \w    108.00 134.00   1.00    2.00    --   67.04  61.00 -90.00   26
 10  \w    104.00 130.00   1.00    2.00    --   67.04 111.00 -90.00   26
 11  \w    109.00 139.00   1.00    2.00    --   67.04 111.00-120.00   30
 12  \w    112.00 143.00   1.00    2.00    --   67.04 118.00-166.00   31
 13  \w    139.00 167.00   1.00    2.00    --  108.00  65.00-180.00   28
 14  \w    130.00 177.00   1.00    2.00    --  108.00  21.00-150.00   47
 15  \w     87.00 142.00   1.00    2.00    --  108.00 138.00-120.00   55
 16  \w     74.00 127.00   1.00    2.00    --  108.00  65.00-180.00   53
 17  \w     82.00 108.00   1.00    2.00    --  108.00  21.00-180.00   26
 18  \w     82.00 107.00   1.00    2.00    --  108.00 -65.00 -60.00   25
 19  \w     85.00 110.00   1.00    2.00    --  108.00-104.00-120.00   25
 20  \w     69.00 109.00   1.00    2.00    --  108.00-104.00 -60.00   40
 21  \w     53.00 102.00   1.00    2.00    --   67.04-111.00 -90.00   49
 22  \w     49.00  74.00   1.00    2.00    --  108.00-104.00 -30.00   25
 23  \w     57.00 100.00   1.00    2.00    --  108.00-104.00  60.00   43
 24  \w     87.00 112.00   1.00    2.00    --  108.00-104.00  90.00   25
 25  \w     85.00 144.00   1.00    2.00    --  108.00 -65.00  90.00   59
 26  \w    148.00 174.00   1.00    2.00    --  108.00 -21.00 150.00   26
 27  \w     90.00 123.00   1.00    2.00    --  108.00 -21.00 150.00   33
 28  \w     93.00 170.00   1.00    2.00    --  108.00  43.00 150.00   77
 29  \w     84.00 175.00   1.00    2.00    --  108.00  54.00  90.00   91
 30  \w     83.00 151.00   1.00    2.00    --  108.00 -89.00 120.00   68
 31  \w     52.00 114.00   1.00    2.00    --  108.00 -77.00  60.00   62
 32  \w     52.00  77.00   1.00    2.00    --  108.00 -21.00 150.00   25
 33  \w     30.00  56.00   1.00    2.00    --  108.00 -65.00  90.00   26
 34  \w     27.00  71.00   1.00    2.00    --  108.00-104.00  90.00   44
 35  \w     -8.00  17.00   1.00    2.00    --   67.04 -61.00 -60.00   25
 36  \w     22.00  84.00   1.00    2.00    --   67.04 -61.00 -60.00   62
 37  \w     29.00  68.00   1.00    2.00    --  108.00-104.00-120.00   39
 38  \w    -29.00  81.00   1.00    1.00    --   26.08 -38.00-180.00  110
 39  \w     65.00 115.00   1.00    2.00    --  108.00  77.00 150.00   50
 40  \w     60.00  85.00   1.00    2.00    --  108.00  43.00 150.00   25
 41  \w     -4.00  87.00   1.00    1.00    --   26.08  57.00 150.00   91
 42  \w     -5.00  94.00   1.00    1.00    --   26.08  57.00  30.00   99
 43  \w     32.00  78.00   1.00    2.00    --   67.04  61.00 -90.00   46
 44  \w     57.00 145.00   1.00    2.00    --   67.04 178.00 -90.00   88
 45  \w    -17.00 151.00   1.00    2.00    --   67.04  15.00  90.00  168
;
_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      -0.0717363000
_diffrn_orient_matrix_UB_12      0.0652949000
_diffrn_orient_matrix_UB_13      0.0838550000
_diffrn_orient_matrix_UB_21      -0.1870542000
_diffrn_orient_matrix_UB_22      -0.0211658000
_diffrn_orient_matrix_UB_23      -0.0490465000
_diffrn_orient_matrix_UB_31      -0.0131770000
_diffrn_orient_matrix_UB_32      -0.1838922000
_diffrn_orient_matrix_UB_33      0.0136187000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0456
_diffrn_reflns_av_unetI/netI     0.0539
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            6172
_diffrn_reflns_point_group_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        66.157
_diffrn_reflns_theta_max         66.157
_diffrn_reflns_theta_min         2.814
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.957
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74683
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41 (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    1.364
_exptl_crystal_description       block
_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.65
_exptl_crystal_size_mid          0.45
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.268
_refine_diff_density_min         -0.393
_refine_diff_density_rms         0.063
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     265
_refine_ls_number_reflns         3366
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0583
_refine_ls_R_factor_gt           0.0495
_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^)+(0.1000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1406
_refine_ls_wR_factor_ref         0.1551
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2829
_reflns_number_total             3366
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ed5019.cif
_cod_data_source_block           tfa-dmap-H2O_1-1-1
_cod_database_code               1557482
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H N O Cl'
_shelx_estimated_absorpt_t_max   0.591
_shelx_estimated_absorpt_t_min   0.363
_reflns_odcompleteness_completeness 96.26
_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,H) groups
2. Restrained distances
 N1-H1 = N3-H3A
 0.87 with sigma of 0.02
3.a Fixed occupancy and ADP/Uiso:
 H1, H3A
3.b Free rotating group:
 O3(H3B,H3C)
3.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C11(H11), C12(H12), C13(H13), C16(H16),
 C17(H17), C18(H18), C19(H19)
3.d Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C20(H20A,H20B,H20C), C21(H21A,H21B,H21C)
;
_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 2.481
_oxdiff_exptl_absorpt_empirical_full_min 0.430