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#$Date: 2025-08-22 18:52:37 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301865 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/22/65/7226513.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_7226513
loop_
_publ_author_name
'Sharma, Raj Pal'
'Kumar, Santosh'
'Venugopalan, P.'
'Ferretti, Valeria'
'Tarushi, Alketa'
'Psomas, George L.'
'Witwicki, Maciej'
_publ_section_title
;
 New copper(II) complexes of anti-inflammatory drug mefenamic acid: a
 concerted study including synthesis, physicochemical characterization and
 their biological evaluation
;
_journal_name_full               'RSC Adv.'
_journal_paper_doi               10.1039/C6RA14706B
_journal_year                    2016
_chemical_formula_moiety         '2(C15 H14 N O2), C4 H20 Cu N4 O2'
_chemical_formula_sum            'C34 H48 Cu N6 O6'
_chemical_formula_weight         700.32
_chemical_name_systematic
Diaqua-bis(ethylenediamine)-copper(ii)bis(mefenamate)
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2015-12-10 deposited with the CCDC.
2016-09-06 downloaded from the CCDC.
;
_cell_angle_alpha                79.714(3)
_cell_angle_beta                 83.229(3)
_cell_angle_gamma                61.736(3)
_cell_formula_units_Z            1
_cell_length_a                   7.6611(4)
_cell_length_b                   7.7237(4)
_cell_length_c                   17.5068(10)
_cell_measurement_reflns_used    10214
_cell_measurement_temperature    295
_cell_measurement_theta_max      27.
_cell_measurement_theta_min      2.
_cell_volume                     897.08(9)
_computing_cell_refinement       'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_data_collection       'Kappa CCD server software (Nonius, 1997)'
_computing_data_reduction        'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'ORTEPIII (Burnett & Johnson, 1996)'
_computing_publication_material
;
SHELXL-2014/7 (Sheldrick, 2014); WINGX (Farrugia, 1999)
;
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SIR97 (Altomare et al.,1999)'
_diffrn_ambient_temperature      295
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_diffrn_measurement_method       'φ scans and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0579
_diffrn_reflns_av_unetI/netI     0.0540
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            10214
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.999
_diffrn_reflns_theta_min         3.570
_exptl_absorpt_coefficient_mu    0.659
_exptl_absorpt_correction_T_max  0.938
_exptl_absorpt_correction_T_min  0.542
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
multi-scan from symmetry-related measurements 
 Sortav (Blessing 1995)
;
_exptl_crystal_colour            'pale violet'
_exptl_crystal_density_diffrn    1.296
_exptl_crystal_description       plate
_exptl_crystal_F_000             371
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.244
_refine_diff_density_min         -0.481
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     230
_refine_ls_number_reflns         4278
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.080
_refine_ls_R_factor_all          0.0618
_refine_ls_R_factor_gt           0.0432
_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/[σ²(Fo²)+(0.0537P)²+0.0858P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1061
_refine_ls_wR_factor_ref         0.1137
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3418
_reflns_number_total             4278
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c6ra14706b2.cif
_cod_data_source_block           mefen1
_cod_database_code               7226513
_shelx_shelxl_version_number     2014/7
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
Cu1 Cu 0.0000 0.0000 0.5000 0.04013(13) Uani 1 2 d S . P
N1 N 0.0643(3) 0.0028(2) 0.38473(10) 0.0464(4) Uani 1 1 d . . .
H2N H 0.1020 0.0971 0.3666 0.056 Uiso 1 1 calc R U .
H3N H 0.1647 -0.1154 0.3754 0.056 Uiso 1 1 calc R U .
O1W O -0.1705(3) 0.3694(3) 0.47026(12) 0.0561(4) Uani 1 1 d . . .
N2 N -0.2461(3) -0.0071(2) 0.47470(10) 0.0447(4) Uani 1 1 d . . .
H4N H -0.2676 -0.0966 0.5095 0.054 Uiso 1 1 calc R U .
H5N H -0.3521 0.1128 0.4766 0.054 Uiso 1 1 calc R U .
C1 C -0.1144(4) 0.0438(3) 0.34496(12) 0.0521(5) Uani 1 1 d . . .
H1A H -0.0768 -0.0031 0.2948 0.063 Uiso 1 1 calc R U .
H1B H -0.2025 0.1855 0.3368 0.063 Uiso 1 1 calc R U .
C2 C -0.2174(4) -0.0624(3) 0.39565(14) 0.0553(6) Uani 1 1 d . . .
H2A H -0.3446 -0.0240 0.3749 0.066 Uiso 1 1 calc R U .
H2B H -0.1374 -0.2049 0.3974 0.066 Uiso 1 1 calc R U .
O1 O 0.1164(3) 0.3664(3) 0.35192(9) 0.0638(5) Uani 1 1 d . . .
O2 O 0.3309(2) 0.3268(2) 0.43556(8) 0.0522(4) Uani 1 1 d . . .
C3 C 0.2506(3) 0.3996(3) 0.37138(12) 0.0428(4) Uani 1 1 d . . .
C4 C 0.3140(3) 0.5339(3) 0.31584(11) 0.0378(4) Uani 1 1 d . . .
C5 C 0.4646(3) 0.5653(3) 0.33808(13) 0.0458(5) Uani 1 1 d . . .
H5 H 0.5185 0.5053 0.3865 0.055 Uiso 1 1 calc R U .
C6 C 0.5361(3) 0.6818(4) 0.29078(14) 0.0547(5) Uani 1 1 d . . .
H6 H 0.6358 0.7014 0.3072 0.066 Uiso 1 1 calc R U .
C7 C 0.4575(3) 0.7694(4) 0.21842(15) 0.0566(6) Uani 1 1 d . . .
H7 H 0.5048 0.8484 0.1860 0.068 Uiso 1 1 calc R U .
C8 C 0.3096(3) 0.7408(3) 0.19387(13) 0.0519(5) Uani 1 1 d . . .
H8 H 0.2615 0.7978 0.1444 0.062 Uiso 1 1 calc R U .
C9 C 0.2304(3) 0.6274(3) 0.24217(11) 0.0418(4) Uani 1 1 d . . .
N3 N 0.0799(3) 0.5994(3) 0.22037(11) 0.0559(5) Uani 1 1 d . . .
C10 C -0.0305(3) 0.6795(3) 0.15257(12) 0.0451(5) Uani 1 1 d . . .
C11 C -0.0895(3) 0.5575(3) 0.12337(12) 0.0470(5) Uani 1 1 d . . .
C12 C -0.2063(3) 0.6359(4) 0.05805(13) 0.0535(5) Uani 1 1 d . . .
C13 C -0.2565(4) 0.8257(4) 0.02267(14) 0.0612(6) Uani 1 1 d . . .
H13 H -0.3288 0.8744 -0.0222 0.073 Uiso 1 1 calc R U .
C14 C -0.2012(4) 0.9459(4) 0.05257(15) 0.0628(6) Uani 1 1 d . . .
H14 H -0.2384 1.0753 0.0285 0.075 Uiso 1 1 calc R U .
C15 C -0.0913(4) 0.8734(3) 0.11796(14) 0.0547(5) Uani 1 1 d . . .
H15 H -0.0575 0.9553 0.1391 0.066 Uiso 1 1 calc R U .
C16 C -0.0305(5) 0.3495(4) 0.16229(15) 0.0684(7) Uani 1 1 d . . .
H16A H -0.1145 0.3519 0.2078 0.103 Uiso 1 1 calc R U .
H16B H 0.1050 0.2882 0.1770 0.103 Uiso 1 1 calc R U .
H16C H -0.0442 0.2749 0.1271 0.103 Uiso 1 1 calc R U .
C17 C -0.2833(4) 0.5149(5) 0.02688(17) 0.0766(8) Uani 1 1 d . . .
H17A H -0.3565 0.5895 -0.0188 0.115 Uiso 1 1 calc R U .
H17B H -0.3685 0.4852 0.0657 0.115 Uiso 1 1 calc R U .
H17C H -0.1736 0.3934 0.0140 0.115 Uiso 1 1 calc R U .
H1W H -0.225(4) 0.459(4) 0.4960(16) 0.064(8) Uiso 1 1 d . . .
H1N H 0.050(4) 0.524(4) 0.2536(14) 0.055(7) Uiso 1 1 d . . .
H2W H -0.101(4) 0.390(4) 0.4403(17) 0.065(9) Uiso 1 1 d . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'
N N 0.0061 0.0033 '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'
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_1
_geom_angle_site_symmetry_3
N2 Cu1 N2 180.0 . 2_556
N2 Cu1 N1 95.25(7) . 2_556
N2 Cu1 N1 84.75(7) 2_556 2_556
N2 Cu1 N1 84.75(7) . .
N2 Cu1 N1 95.25(7) 2_556 .
N1 Cu1 N1 180.0 2_556 .
C1 N1 Cu1 108.83(13) . .
C1 N1 H2N 109.9 . .
Cu1 N1 H2N 109.9 . .
C1 N1 H3N 109.9 . .
Cu1 N1 H3N 109.9 . .
H2N N1 H3N 108.3 . .
H1W O1W H2W 110(3) . .
C2 N2 Cu1 108.36(13) . .
C2 N2 H4N 110.0 . .
Cu1 N2 H4N 110.0 . .
C2 N2 H5N 110.0 . .
Cu1 N2 H5N 110.0 . .
H4N N2 H5N 108.4 . .
N1 C1 C2 107.99(17) . .
N1 C1 H1A 110.1 . .
C2 C1 H1A 110.1 . .
N1 C1 H1B 110.1 . .
C2 C1 H1B 110.1 . .
H1A C1 H1B 108.4 . .
N2 C2 C1 108.02(17) . .
N2 C2 H2A 110.1 . .
C1 C2 H2A 110.1 . .
N2 C2 H2B 110.1 . .
C1 C2 H2B 110.1 . .
H2A C2 H2B 108.4 . .
O2 C3 O1 122.47(19) . .
O2 C3 C4 118.69(18) . .
O1 C3 C4 118.83(17) . .
C5 C4 C9 118.81(18) . .
C5 C4 C3 117.71(17) . .
C9 C4 C3 123.47(17) . .
C6 C5 C4 122.2(2) . .
C6 C5 H5 118.9 . .
C4 C5 H5 118.9 . .
C5 C6 C7 118.9(2) . .
C5 C6 H6 120.5 . .
C7 C6 H6 120.5 . .
C6 C7 C8 120.8(2) . .
C6 C7 H7 119.6 . .
C8 C7 H7 119.6 . .
C7 C8 C9 121.2(2) . .
C7 C8 H8 119.4 . .
C9 C8 H8 119.4 . .
N3 C9 C8 122.85(19) . .
N3 C9 C4 119.10(18) . .
C8 C9 C4 118.03(19) . .
C9 N3 C10 130.03(19) . .
C9 N3 H1N 113.5(16) . .
C10 N3 H1N 116.4(16) . .
C15 C10 C11 120.20(19) . .
C15 C10 N3 122.42(18) . .
C11 C10 N3 117.26(18) . .
C12 C11 C10 118.5(2) . .
C12 C11 C16 120.94(19) . .
C10 C11 C16 120.54(19) . .
C13 C12 C11 120.0(2) . .
C13 C12 C17 119.3(2) . .
C11 C12 C17 120.7(2) . .
C12 C13 C14 121.1(2) . .
C12 C13 H13 119.4 . .
C14 C13 H13 119.4 . .
C15 C14 C13 119.7(2) . .
C15 C14 H14 120.2 . .
C13 C14 H14 120.2 . .
C14 C15 C10 120.4(2) . .
C14 C15 H15 119.8 . .
C10 C15 H15 119.8 . .
C11 C16 H16A 109.5 . .
C11 C16 H16B 109.5 . .
H16A C16 H16B 109.5 . .
C11 C16 H16C 109.5 . .
H16A C16 H16C 109.5 . .
H16B C16 H16C 109.5 . .
C12 C17 H17A 109.5 . .
C12 C17 H17B 109.5 . .
H17A C17 H17B 109.5 . .
C12 C17 H17C 109.5 . .
H17A C17 H17C 109.5 . .
H17B C17 H17C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cu1 N2 2.0147(16) .
Cu1 N2 2.0147(16) 2_556
Cu1 N1 2.0188(17) 2_556
Cu1 N1 2.0188(17) .
N1 C1 1.482(3) .
N1 H2N 0.9000 .
N1 H3N 0.9000 .
O1W H1W 0.80(3) .
O1W H2W 0.76(3) .
N2 C2 1.482(3) .
N2 H4N 0.9000 .
N2 H5N 0.9000 .
C1 C2 1.507(3) .
C1 H1A 0.9700 .
C1 H1B 0.9700 .
C2 H2A 0.9700 .
C2 H2B 0.9700 .
O1 C3 1.265(2) .
O2 C3 1.252(2) .
C3 C4 1.504(3) .
C4 C5 1.395(3) .
C4 C9 1.421(3) .
C5 C6 1.374(3) .
C5 H5 0.9300 .
C6 C7 1.383(3) .
C6 H6 0.9300 .
C7 C8 1.379(3) .
C7 H7 0.9300 .
C8 C9 1.403(3) .
C8 H8 0.9300 .
C9 N3 1.375(3) .
N3 C10 1.409(3) .
N3 H1N 0.84(3) .
C10 C15 1.382(3) .
C10 C11 1.408(3) .
C11 C12 1.399(3) .
C11 C16 1.498(3) .
C12 C13 1.371(4) .
C12 C17 1.516(3) .
C13 C14 1.384(4) .
C13 H13 0.9300 .
C14 C15 1.373(3) .
C14 H14 0.9300 .
C15 H15 0.9300 .
C16 H16A 0.9600 .
C16 H16B 0.9600 .
C16 H16C 0.9600 .
C17 H17A 0.9600 .
C17 H17B 0.9600 .
C17 H17C 0.9600 .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139202727
