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#$Date: 2025-08-18 17:20:24 +0300 (Mon, 18 Aug 2025) $
#$Revision: 301776 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/51/89/1518961.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1518961
loop_
_publ_author_name
'Wittering, K. E.'
'Agnew, L. R.'
'Klapwijk, A. R.'
'Robertson, K.'
'Cousen, A. J. P.'
'Cruickshank, D. L.'
'Wilson, C. C.'
_publ_section_title
;
 Crystallisation and physicochemical property characterisation of
 conformationally-locked co-crystals of fenamic acid derivatives
;
_journal_issue                   19
_journal_name_full               CrystEngComm
_journal_page_first              3610
_journal_paper_doi               10.1039/C5CE00297D
_journal_volume                  17
_journal_year                    2015
_chemical_formula_moiety         'C15 H15 N1 O2, 0.5(C10 H8 N2)'
_chemical_formula_sum            'C20 H19 N2 O2'
_chemical_formula_weight         319.37
_chemical_name_common
;
mefenamic acid and 4,4'-Bipyridine complex
;
_chemical_name_systematic
'2-(2,3-dimethylphenyl)aminobenzoic acid and 4,4'bipyridine complex'
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2014-08-10 deposited with the CCDC.
2015-03-30 downloaded from the CCDC.
;
_cell_angle_alpha                106.135(4)
_cell_angle_beta                 99.428(4)
_cell_angle_gamma                98.758(4)
_cell_formula_units_Z            2
_cell_length_a                   7.3086(3)
_cell_length_b                   8.6692(4)
_cell_length_c                   13.6320(5)
_cell_measurement_reflns_used    5336
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      29.5773
_cell_measurement_theta_min      2.8830
_cell_volume                     800.46(6)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 10.3795
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.890
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0444
_diffrn_reflns_av_sigmaI/netI    0.0403
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            17917
_diffrn_reflns_theta_full        25.24
_diffrn_reflns_theta_max         29.64
_diffrn_reflns_theta_min         2.89
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86518
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.325
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             338
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.188
_refine_diff_density_min         -0.206
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     293
_refine_ls_number_reflns         4011
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.017
_refine_ls_R_factor_all          0.0769
_refine_ls_R_factor_gt           0.0485
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0457P)²+0.1998P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1008
_refine_ls_wR_factor_ref         0.1137
_reflns_number_gt                2899
_reflns_number_total             4011
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5ce00297d2.cif
_cod_data_source_block           c:\xrd\mef44b~1\final\p13ccw81
_cod_depositor_comments
'Adding full bibliography for 1518960--1518962.cif.'
_cod_database_code               1518961
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
O1 O 0.15336(16) 0.75893(14) 0.40874(8) 0.0378(3) Uani 1 1 d
N1 N 0.30610(19) 0.07981(16) 0.45943(10) 0.0363(3) Uani 1 1 d
H1 H 0.206(3) 0.875(3) 0.4270(17) 0.077(7) Uiso 1 1 d
O2 O 0.26994(16) 0.75237(12) 0.26775(8) 0.0378(3) Uani 1 1 d
C3 C 0.1896(2) 0.67917(18) 0.31838(11) 0.0282(3) Uani 1 1 d
C4 C 0.12566(19) 0.49980(17) 0.28557(10) 0.0260(3) Uani 1 1 d
C5 C 0.0333(2) 0.4262(2) 0.34845(12) 0.0322(3) Uani 1 1 d
H5 H 0.014(2) 0.4985(19) 0.4134(13) 0.033(4) Uiso 1 1 d
H12 H 0.075(2) 0.411(2) -0.0648(12) 0.036(4) Uiso 1 1 d
H10 H 0.283(3) 0.574(2) 0.1484(14) 0.046(5) Uiso 1 1 d
H17B H 0.539(3) 0.392(2) 0.2006(16) 0.058(6) Uiso 1 1 d
H23 H 0.414(2) 0.037(2) 0.3368(14) 0.049(5) Uiso 1 1 d
H18C H 0.670(2) 0.066(2) -0.0092(14) 0.045(5) Uiso 1 1 d
H18B H 0.793(3) 0.230(2) -0.0138(14) 0.053(5) Uiso 1 1 d
H6 H -0.088(2) 0.211(2) 0.3659(14) 0.045(5) Uiso 1 1 d
H20 H 0.338(3) 0.438(2) 0.6171(14) 0.051(5) Uiso 1 1 d
H19 H 0.213(3) 0.162(2) 0.5880(15) 0.055(5) Uiso 1 1 d
H17A H 0.708(3) 0.347(2) 0.1472(14) 0.056(6) Uiso 1 1 d
H17C H 0.562(3) 0.208(3) 0.1579(15) 0.060(6) Uiso 1 1 d
H22 H 0.555(3) 0.312(2) 0.3553(15) 0.054(5) Uiso 1 1 d
C6 C -0.0251(2) 0.2588(2) 0.32180(13) 0.0379(4) Uani 1 1 d
C7 C 0.0085(2) 0.1609(2) 0.23017(13) 0.0366(4) Uani 1 1 d
H7 H -0.029(2) 0.043(2) 0.2085(12) 0.037(4) Uiso 1 1 d
H13 H 0.155(2) 0.2697(19) -0.2210(13) 0.037(4) Uiso 1 1 d
C8 C 0.0976(2) 0.22832(18) 0.16587(12) 0.0302(3) Uani 1 1 d
H8 H 0.120(2) 0.156(2) 0.1019(13) 0.035(4) Uiso 1 1 d
C9 C 0.15840(19) 0.39887(16) 0.19121(10) 0.0250(3) Uani 1 1 d
N10 N 0.24471(18) 0.46465(15) 0.12594(9) 0.0289(3) Uani 1 1 d
C11 C 0.2941(2) 0.37161(16) 0.03364(10) 0.0248(3) Uani 1 1 d
C12 C 0.1846(2) 0.35991(17) -0.06243(11) 0.0278(3) Uani 1 1 d
C13 C 0.2332(2) 0.27747(18) -0.15358(11) 0.0301(3) Uani 1 1 d
C14 C 0.3894(2) 0.20628(17) -0.14846(11) 0.0274(3) Uani 1 1 d
H14 H 0.424(2) 0.1473(19) -0.2135(12) 0.034(4) Uiso 1 1 d
H18A H 0.686(2) 0.085(2) -0.1217(14) 0.046(5) Uiso 1 1 d
C15 C 0.50086(19) 0.21647(16) -0.05306(11) 0.0250(3) Uani 1 1 d
C16 C 0.4528(2) 0.30041(16) 0.04002(10) 0.0248(3) Uani 1 1 d
C17 C 0.5719(2) 0.3135(2) 0.14361(12) 0.0336(3) Uani 1 1 d
C18 C 0.6737(2) 0.1424(2) -0.04983(13) 0.0333(3) Uani 1 1 d
C19 C 0.2864(3) 0.1982(2) 0.54063(13) 0.0413(4) Uani 1 1 d
C20 C 0.3594(2) 0.3614(2) 0.55962(12) 0.0384(4) Uani 1 1 d
C21 C 0.4611(2) 0.41203(18) 0.49233(11) 0.0298(3) Uani 1 1 d
C22 C 0.4836(3) 0.2878(2) 0.40858(12) 0.0398(4) Uani 1 1 d
C23 C 0.4058(3) 0.1280(2) 0.39519(13) 0.0402(4) Uani 1 1 d
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_3
C3 O1 H1 110.3(13) .
C19 N1 C23 116.07(14) .
O2 C3 O1 121.18(13) .
O2 C3 C4 123.83(12) .
O1 C3 C4 114.99(12) .
C5 C4 C9 119.14(13) .
C5 C4 C3 119.93(13) .
C9 C4 C3 120.93(12) .
C6 C5 C4 121.79(15) .
C6 C5 H5 120.9(9) .
C4 C5 H5 117.3(9) .
C5 C6 C7 118.84(14) .
C5 C6 H6 120.5(10) .
C7 C6 H6 120.7(10) .
C8 C7 C6 121.20(15) .
C8 C7 H7 117.0(10) .
C6 C7 H7 121.8(10) .
C7 C8 C9 121.08(14) .
C7 C8 H8 119.4(9) .
C9 C8 H8 119.5(9) .
N10 C9 C8 120.55(13) .
N10 C9 C4 121.51(12) .
C8 C9 C4 117.94(12) .
C9 N10 C11 124.86(11) .
C9 N10 H10 115.4(11) .
C11 N10 H10 119.4(11) .
C12 C11 C16 121.06(13) .
C12 C11 N10 118.07(12) .
C16 C11 N10 120.82(12) .
C13 C12 C11 119.79(14) .
C13 C12 H12 120.7(9) .
C11 C12 H12 119.5(9) .
C14 C13 C12 119.78(14) .
C14 C13 H13 121.0(10) .
C12 C13 H13 119.2(10) .
C13 C14 C15 121.35(13) .
C13 C14 H14 119.7(9) .
C15 C14 H14 118.9(9) .
C14 C15 C16 119.26(13) .
C14 C15 C18 120.18(13) .
C16 C15 C18 120.54(13) .
C11 C16 C15 118.76(13) .
C11 C16 C17 121.20(13) .
C15 C16 C17 120.04(13) .
C16 C17 H17B 111.3(12) .
C16 C17 H17A 112.4(11) .
H17B C17 H17A 107.9(16) .
C16 C17 H17C 112.9(11) .
H17B C17 H17C 108.7(16) .
H17A C17 H17C 103.3(16) .
C15 C18 H18C 111.5(10) .
C15 C18 H18B 111.0(11) .
H18C C18 H18B 105.5(15) .
C15 C18 H18A 110.9(10) .
H18C C18 H18A 109.4(14) .
H18B C18 H18A 108.4(14) .
N1 C19 C20 123.72(16) .
N1 C19 H19 115.6(11) .
C20 C19 H19 120.7(11) .
C19 C20 C21 120.33(14) .
C19 C20 H20 119.4(12) .
C21 C20 H20 120.2(12) .
C22 C21 C20 115.72(15) .
C22 C21 C21 121.74(17) 2_666
C20 C21 C21 122.53(16) 2_666
C23 C22 C21 120.23(15) .
C23 C22 H22 118.0(11) .
C21 C22 H22 121.7(11) .
N1 C23 C22 123.92(14) .
N1 C23 H23 112.6(11) .
C22 C23 H23 123.5(11) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C3 1.3248(16) .
O1 H1 0.97(2) .
N1 C19 1.328(2) .
N1 C23 1.339(2) .
O2 C3 1.2191(17) .
C3 C4 1.470(2) .
C4 C5 1.4002(19) .
C4 C9 1.4200(19) .
C5 C6 1.374(2) .
C5 H5 0.976(16) .
C6 C7 1.384(2) .
C6 H6 0.957(18) .
C7 C8 1.375(2) .
C7 H7 0.961(17) .
C8 C9 1.403(2) .
C8 H8 0.977(17) .
C9 N10 1.3679(17) .
N10 C11 1.4274(17) .
N10 H10 0.891(19) .
C11 C12 1.387(2) .
C11 C16 1.3962(19) .
C12 C13 1.382(2) .
C12 H12 0.974(17) .
C13 C14 1.379(2) .
C13 H13 0.979(17) .
C14 C15 1.389(2) .
C14 H14 0.985(16) .
C15 C16 1.4048(19) .
C15 C18 1.502(2) .
C16 C17 1.498(2) .
C17 H17B 0.97(2) .
C17 H17A 0.98(2) .
C17 H17C 0.98(2) .
C18 H18C 0.974(18) .
C18 H18B 1.01(2) .
C18 H18A 0.995(18) .
C19 C20 1.370(2) .
C19 H19 0.990(19) .
C20 C21 1.391(2) .
C20 H20 0.929(19) .
C21 C22 1.386(2) .
C21 C21 1.488(3) 2_666
C22 C23 1.365(2) .
C22 H22 1.012(19) .
C23 H23 0.971(18) .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139044818
