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_1557483
_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, C14 H11 Cl N O2, C7 H11 N2'
_chemical_formula_sum            'C35 H34 Cl2 N4 O4'
_chemical_formula_weight         645.56
_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             2019-10-10
_audit_creation_method
;
Olex2 1.3
(compiled 2019.09.11 svn.r3662 for OlexSys, GUI svn.r5938)
;
_cell_angle_alpha                106.966(6)
_cell_angle_beta                 105.782(6)
_cell_angle_gamma                103.324(5)
_cell_formula_units_Z            2
_cell_length_a                   10.8864(7)
_cell_length_b                   12.2705(7)
_cell_length_c                   13.7811(10)
_cell_measurement_reflns_used    2351
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.3500
_cell_measurement_theta_min      3.9140
_cell_volume                     1595.5(2)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33c (release 11-04-2014 CrysAlis171 .NET)
(compiled Apr 11 2014,15:12:41)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33c (release 11-04-2014 CrysAlis171 .NET)
(compiled Apr 11 2014,15:12:41)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33c (release 11-04-2014 CrysAlis171 .NET)
(compiled Apr 11 2014,15:12:41)
;
_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_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 7.9580
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_details
;
  1 omega  -87.00  -61.00   1.0000   45.0000
omega____ theta____ kappa____ phi______ frames
    -      -29.5717  178.0000   30.0000 26

  2 omega   39.00  111.00   1.0000   45.0000
omega____ theta____ kappa____ phi______ frames
    -       30.9779  178.0000  -60.0000 72

  3 omega  -20.00   85.00   1.0000   45.0000
omega____ theta____ kappa____ phi______ frames
    -       30.9779  -99.0000    0.0000 105

  4 omega  -20.00   49.00   1.0000   45.0000
omega____ theta____ kappa____ phi______ frames
    -       30.9779  -99.0000  -60.0000 69

  5 omega  -55.00  127.00   1.0000   45.0000
omega____ theta____ kappa____ phi______ frames
    -       30.9779  -19.0000    0.0000 182
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0370971000
_diffrn_orient_matrix_UB_12      0.0009268000
_diffrn_orient_matrix_UB_13      -0.0350149000
_diffrn_orient_matrix_UB_21      0.0121346000
_diffrn_orient_matrix_UB_22      0.0629540000
_diffrn_orient_matrix_UB_23      0.0141477000
_diffrn_orient_matrix_UB_31      0.0603936000
_diffrn_orient_matrix_UB_32      0.0125219000
_diffrn_orient_matrix_UB_33      0.0437821000
_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  0.0223
_diffrn_reflns_av_unetI/netI     0.0451
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            8477
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        25.027
_diffrn_reflns_theta_max         25.027
_diffrn_reflns_theta_min         3.916
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.249
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.73906
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33c (release 11-04-2014 CrysAlis171 .NET)
(compiled Apr 11 2014,15:12:41)
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    1.344
_exptl_crystal_description       block
_exptl_crystal_F_000             676
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.362
_refine_diff_density_min         -0.163
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     582
_refine_ls_number_reflns         5577
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.1060
_refine_ls_R_factor_gt           0.0755
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0721P)^2^+1.2105P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1831
_refine_ls_wR_factor_ref         0.2038
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3784
_reflns_number_total             5577
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ed5019.cif
_cod_data_source_block           tfa-dmap_2-1
_cod_original_cell_volume        1595.53(19)
_cod_database_code               1557483
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H N O'
_shelx_estimated_absorpt_t_max   0.976
_shelx_estimated_absorpt_t_min   0.920
_reflns_odcompleteness_completeness 98.74
_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, All O(H) groups
2. Restrained distances
 N5-H5 = N2-H2 = N4-H4A = N6-H6A = N1-H1
 0.87 with sigma of 0.02
 O3-H3
 0.82 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C49) = Uanis(C10)
Uanis(C47) = Uanis(C25)
4. Others
 Sof(Cl3)=Sof(Cl4)=Sof(N5)=Sof(H5)=Sof(C43)=Sof(H43)=Sof(C40)=Sof(C42)=
 Sof(C46)=Sof(C41)=Sof(H41)=Sof(C48)=Sof(H48A)=Sof(H48B)=Sof(H48C)=Sof(C39)=
 Sof(C44)=Sof(H44)=Sof(C36)=Sof(H36)=Sof(C47)=Sof(H47)=Sof(C37)=Sof(H37A)=
 Sof(H37B)=Sof(H37C)=Sof(C49)=Sof(C38)=Sof(H38)=Sof(C45)=1-FVAR(1)
 Sof(Cl2)=Sof(N2)=Sof(H2)=Sof(C22)=Sof(C23)=Sof(C24)=Sof(C25)=Sof(H25)=
 Sof(C26)=Sof(H26)=Sof(C27)=Sof(H27)=Sof(C28)=Sof(H28A)=Sof(H28B)=Sof(H28C)=
 Sof(Cl1)=Sof(C8)=Sof(C9)=Sof(C10)=Sof(C11)=Sof(H11)=Sof(C12)=Sof(H12)=Sof(C13)=
 Sof(H13)=Sof(C14)=Sof(H14A)=Sof(H14B)=Sof(H14C)=FVAR(1)
 Sof(N6)=Sof(H6A)=1-FVAR(2)
 Sof(N1)=Sof(H1)=FVAR(2)
5.a Fixed occupancy and ADP/Uiso:
 H3, H2, H1, H4A, H5, H6A
5.b Aromatic/amide H refined with riding coordinates:
 C17(H17), C18(H18), C19(H19), C20(H20), C25(H25), C26(H26), C27(H27), C3(H3A),
  C4(H4), C5(H5A), C6(H6), C11(H11), C12(H12), C13(H13), C30(H30), C31(H31),
 C32(H32), C33(H33), C43(H43), C41(H41), C44(H44), C36(H36), C47(H47), C38(H38)
5.c Idealised Me refined as rotating group:
 C28(H28A,H28B,H28C), C14(H14A,H14B,H14C), C34(H34A,H34B,H34C), C35(H35A,H35B,
 H35C), C48(H48A,H48B,H48C), C37(H37A,H37B,H37C)
;
_olex2_submission_special_instructions 'No special instructions were received'