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_1557481
_publ_section_title
;
 Isomorphism: `molecular similarity to crystal structure similarity' in
 multicomponent forms of analgesic drugs tolfenamic and mefenamic acid
;
_journal_coeditor_code           ED5019
_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'
_chemical_formula_sum            'C21 H22 Cl N3 O2'
_chemical_formula_weight         383.86
_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                87.768(4)
_cell_angle_beta                 76.928(5)
_cell_angle_gamma                76.025(5)
_cell_formula_units_Z            2
_cell_length_a                   7.9299(5)
_cell_length_b                   9.3219(4)
_cell_length_c                   13.5862(9)
_cell_measurement_reflns_used    2867
_cell_measurement_temperature    290.80(10)
_cell_measurement_theta_max      26.2780
_cell_measurement_theta_min      2.2390
_cell_volume                     949.20(10)
_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      air
_diffrn_ambient_temperature      290.80(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 7.9580
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.993
_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    -53.00 -27.00   1.00    4.11    --    0.70  38.00-180.00   26
  2  \w     50.00  83.00   1.00    4.11    --    0.70  38.00-180.00   33
  3  \w   -100.00 -75.00   1.00    4.11    --    0.70 178.00  60.00   25
  4  \w     -5.00  21.00   1.00    4.11    --    0.70  38.00-180.00   26
  5  \w    -20.00   5.00   1.00   25.00    --  -29.42 -99.00   0.00   25
  6  \w   -111.00 -75.00   1.00   25.00    --  -29.42 178.00-180.00   36
  7  \w   -120.00 -60.00   1.00   25.00    --  -29.42 178.00 -30.00   60
  8  \w    -50.00  62.00   1.00   25.00    --   30.82 -38.00  60.00  112
  9  \w     72.00 107.00   1.00   25.00    --   30.82 178.00 -60.00   35
 10  \w    -56.00  71.00   1.00   25.00    --   30.82 -38.00-180.00  127
 11  \w    -49.00  71.00   1.00   25.00    --   30.82 -38.00 -60.00  120
;
_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      0.0898718000
_diffrn_orient_matrix_UB_12      -0.0132888000
_diffrn_orient_matrix_UB_13      -0.0274577000
_diffrn_orient_matrix_UB_21      -0.0258190000
_diffrn_orient_matrix_UB_22      -0.0186290000
_diffrn_orient_matrix_UB_23      -0.0436053000
_diffrn_orient_matrix_UB_31      -0.0141259000
_diffrn_orient_matrix_UB_32      0.0750085000
_diffrn_orient_matrix_UB_33      -0.0147654000
_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  0.0217
_diffrn_reflns_av_unetI/netI     0.0342
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            6616
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.368
_diffrn_reflns_theta_min         2.707
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.223
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79133
_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    1.343
_exptl_crystal_description       block
_exptl_crystal_F_000             404
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.163
_refine_diff_density_min         -0.265
_refine_diff_density_rms         0.036
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     339
_refine_ls_number_reflns         3841
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0783
_refine_ls_R_factor_gt           0.0567
_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^)+(0.0595P)^2^+0.3245P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1406
_refine_ls_wR_factor_ref         0.1544
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2799
_reflns_number_total             3841
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ed5019.cif
_cod_data_source_block           tfa_dmap_1-1
_cod_database_code               1557481
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H N O Cl'
_shelx_estimated_absorpt_t_max   0.978
_shelx_estimated_absorpt_t_min   0.932
_reflns_odcompleteness_completeness 99.64
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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
2. Restrained distances
 N1-H1 = N4-H4A
 0.87 with sigma of 0.02
 N3-H3A
 0.87 with sigma of 0.02
3. Others
 Sof(N4)=Sof(H4A)=Sof(C24)=Sof(C27)=Sof(H27)=Sof(C28)=Sof(H28)=Sof(C23)=
 Sof(C26)=Sof(H26)=Sof(C25)=Sof(Cl2)=Sof(C22)=Sof(H22A)=Sof(H22B)=Sof(H22C)=1-
 FVAR(1)
 Sof(Cl1)=Sof(N1)=Sof(H1)=Sof(C9)=Sof(H9)=Sof(C13)=Sof(C12)=Sof(C14)=Sof(H14A)=
 Sof(H14B)=Sof(H14C)=Sof(C11)=Sof(H11)=Sof(C8)=Sof(C10)=Sof(H10)=FVAR(1)
4.a Fixed occupancy and ADP/Uiso:
 H3A, H1, H4A
4.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C18(H18), C19(H19), C16(H16), C4(H4), C17(H17), C5(H5), C6(H6),
 C9(H9), C11(H11), C10(H10), C27(H27), C28(H28), C26(H26)
4.c Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C), C20(H20A,H20B,H20C), C14(H14A,H14B,H14C), C22(H22A,H22B,
 H22C)
;
_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 1.338
_oxdiff_exptl_absorpt_empirical_full_min 0.750