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_1557488
_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         'C15 H14 N O2, C15 H15 N O2, C7 H11 N2'
_chemical_formula_sum            'C37 H40 N4 O4'
_chemical_formula_weight         604.73
_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                106.152(7)
_cell_angle_beta                 105.842(7)
_cell_angle_gamma                103.490(7)
_cell_formula_units_Z            2
_cell_length_a                   10.7678(8)
_cell_length_b                   11.9673(10)
_cell_length_c                   13.7860(11)
_cell_measurement_reflns_used    1757
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      50.8090
_cell_measurement_theta_min      3.5620
_cell_volume                     1546.9(3)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_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      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 7.9580
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.971
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_details
;
  1 omega  -50.00   62.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       26.3311  -57.0000  -30.0000 112

  2 omega  -50.00   61.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       26.3311  -57.0000 -150.0000 111

  3 omega  -50.00   64.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       26.3311  -57.0000   90.0000 114

  4 omega   68.00  158.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       77.2396  -25.0000  150.0000 90

  5 omega   21.00   47.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       77.2396 -111.0000  120.0000 26

  6 omega    3.00  113.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       77.2396  -63.0000  150.0000 110

  7 omega  125.00  153.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       77.2396  -25.0000    0.0000 28

  8 omega  126.00  162.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       77.2396  111.0000  120.0000 36

  9 omega    0.00  106.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       77.2396  -25.0000    0.0000 106

 10 omega   21.00  107.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       77.2396 -111.0000  -30.0000 86

 11 omega    4.00   59.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       77.2396  -25.0000  150.0000 55

 12 omega   69.00  116.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       77.2396 -111.0000  120.0000 47

 13 omega   27.00  103.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       77.2396   38.0000   30.0000 76

 14 omega  131.00  157.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       77.2396   38.0000   30.0000 26

 15 omega    4.00  116.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       77.2396  -77.0000   30.0000 112
;
_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      -0.0292435000
_diffrn_orient_matrix_UB_12      0.0607721000
_diffrn_orient_matrix_UB_13      0.1016710000
_diffrn_orient_matrix_UB_21      0.0825070000
_diffrn_orient_matrix_UB_22      0.1282066000
_diffrn_orient_matrix_UB_23      0.0079061000
_diffrn_orient_matrix_UB_31      -0.1313175000
_diffrn_orient_matrix_UB_32      0.0098216000
_diffrn_orient_matrix_UB_33      -0.0719266000
_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  0.0524
_diffrn_reflns_av_unetI/netI     0.0541
_diffrn_reflns_Laue_measured_fraction_full 0.971
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            4616
_diffrn_reflns_point_group_measured_fraction_full 0.971
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_theta_full        50.904
_diffrn_reflns_theta_max         50.904
_diffrn_reflns_theta_min         3.580
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.680
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.94167
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
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    1.298
_exptl_crystal_description       needle
_exptl_crystal_F_000             644
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.258
_refine_diff_density_min         -0.252
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     525
_refine_ls_number_reflns         3203
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0807
_refine_ls_R_factor_gt           0.0637
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1036P)^2^+0.6853P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1701
_refine_ls_wR_factor_ref         0.1862
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2494
_reflns_number_total             3203
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ed5019.cif
_cod_data_source_block           mfa-dmap_2-1
_cod_original_cell_volume        1546.9(2)
_cod_database_code               1557488
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H N O'
_shelx_estimated_absorpt_t_max   0.876
_shelx_estimated_absorpt_t_min   0.754
_reflns_odcompleteness_completeness 97.99
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     50.38
_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
 N4-H4A = N8-H8 = N1-H1 = N9-H9 = N2-H2
 0.87 with sigma of 0.02
 O3-H3
 0.82 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C38) = Uanis(C42)
Uanis(C24) = Uanis(C25)
Uanis(C23) = Uanis(C51)
Uanis(C50) = Uanis(C44)
Uanis(C13) = Uanis(C12)
Uanis(C41) = Uanis(C52)
Uanis(C45) = Uanis(C8)
Uanis(C12) = Uanis(C13) = Uanis(C52) = Uanis(C41)
Uanis(C28) = Uanis(C27)
Uanis(N1) = Uanis(N8) = Uanis(N9) = Uanis(N2)
4. Others
 Sof(C49)=Sof(H49)=Sof(C50)=Sof(H50)=Sof(C38)=Sof(C40)=Sof(H40A)=Sof(H40B)=
 Sof(H40C)=Sof(C41)=Sof(C45)=Sof(C46)=Sof(H46A)=Sof(H46B)=Sof(H46C)=Sof(N8)=
 Sof(H8)=Sof(N9)=Sof(H9)=Sof(C51)=Sof(C39)=Sof(H39A)=Sof(H39B)=Sof(H39C)=
 Sof(C43)=Sof(H43A)=Sof(H43B)=Sof(H43C)=Sof(C47)=Sof(H47)=Sof(C42)=Sof(C44)=
 Sof(H44)=Sof(C48)=Sof(H48)=Sof(C52)=Sof(C53)=Sof(H53)=1-FVAR(1)
 Sof(N2)=Sof(H2)=Sof(N1)=Sof(H1)=Sof(C25)=Sof(C12)=Sof(C28)=Sof(H28)=Sof(C26)=
 Sof(H26)=Sof(C8)=Sof(C29)=Sof(H29A)=Sof(H29B)=Sof(H29C)=Sof(C15)=Sof(H15A)=
 Sof(H15B)=Sof(H15C)=Sof(C11)=Sof(H11)=Sof(C23)=Sof(C9)=Sof(H9A)=Sof(C24)=
 Sof(C13)=Sof(C27)=Sof(H27)=Sof(C30)=Sof(H30A)=Sof(H30B)=Sof(H30C)=Sof(C14)=
 Sof(H14A)=Sof(H14B)=Sof(H14C)=Sof(C10)=Sof(H10)=FVAR(1)
5.a Fixed occupancy and ADP/Uiso:
 H3, H4A, H2, H8
5.b Aromatic/amide H refined with riding coordinates:
 C21(H21), C33(H33), C4(H4), C6(H6), C32(H32), C5(H5), C34(H34), C20(H20),
 C35(H35), C3(H3A), C18(H18), C19(H19), C28(H28), C26(H26), C11(H11), C9(H9A),
 C27(H27), C10(H10), C49(H49), C50(H50), C47(H47), C44(H44), C48(H48), C53(H53)
5.c Idealised Me refined as rotating group:
 C36(H36A,H36B,H36C), C37(H37A,H37B,H37C), C29(H29A,H29B,H29C), C15(H15A,H15B,
 H15C), C30(H30A,H30B,H30C), C14(H14A,H14B,H14C), C40(H40A,H40B,H40C), C46(H46A,
 H46B,H46C), C39(H39A,H39B,H39C), C43(H43A,H43B,H43C)
;
_olex2_submission_special_instructions 'No special instructions were received'