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#$Date: 2021-07-07 12:32:00 +0300 (Wed, 07 Jul 2021) $
#$Revision: 267342 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/40/1564015.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_1564015
loop_
_publ_author_name
'Shamle, Nathaniel J.'
'Tella, Adedibu C.'
'Obaleye, Joshua A.'
'Balogun, Fatai O.'
'Ashafa, Anofi O.T.'
'Ajibade, Peter A.'
_publ_section_title
;
 Synthesis, characterization, antioxidant and antidiabetic studies of
 Cu(II) and Zn(II) complexes of tolfenamic acid/mefenamic acid with
 1-methylimidazole
;
_journal_name_full               'Inorganica Chimica Acta'
_journal_page_first              119942
_journal_paper_doi               10.1016/j.ica.2020.119942
_journal_volume                  513
_journal_year                    2020
_chemical_formula_moiety         'C18 H17 Cl Cu0.50 N3 O2'
_chemical_formula_sum            'C18 H17 Cl Cu0.5 N3 O2'
_chemical_formula_weight         374.56
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014
_cell_angle_alpha                90
_cell_angle_beta                 99.332(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   17.1782(16)
_cell_length_b                   12.2459(11)
_cell_length_c                   8.0393(7)
_cell_measurement_reflns_used    9891
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.18
_cell_measurement_theta_min      2.40
_cell_volume                     1668.8(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0339
_diffrn_reflns_av_unetI/netI     0.0233
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            30062
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.257
_diffrn_reflns_theta_min         1.201
_exptl_absorpt_coefficient_mu    0.865
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6780
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.491
_exptl_crystal_description       rod-like
_exptl_crystal_F_000             774
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.578
_refine_diff_density_min         -0.529
_refine_diff_density_rms         0.059
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     225
_refine_ls_number_reflns         4123
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0340
_refine_ls_R_factor_gt           0.0291
_refine_ls_shift/su_max          0.038
_refine_ls_shift/su_mean         0.004
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0296P)²+1.4218P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0726
_refine_ls_wR_factor_ref         0.0755
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3652
_reflns_number_total             4123
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            PA_FA_128.cif
_cod_data_source_block           shelx
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_original_formula_sum        'C18 H17 Cl Cu0.50 N3 O2'
_cod_database_code               1564015
_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.
;
_shelxl_version_number           2014-3
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.5000 0.5000 0.0000 0.00984(7) Uani 1 2 d S . P . .
Cl1 Cl 0.88148(3) 0.96765(3) 0.35041(7) 0.02946(11) Uani 1 1 d . . . . .
O1 O 0.58878(6) 0.40040(8) 0.07558(13) 0.0129(2) Uani 1 1 d . . . . .
O2 O 0.63706(6) 0.56215(9) 0.16239(14) 0.0147(2) Uani 1 1 d . . . . .
N1 N 0.54080(7) 0.52682(10) -0.21389(16) 0.0123(2) Uani 1 1 d . . . . .
N2 N 0.56158(7) 0.61526(10) -0.44138(16) 0.0131(3) Uani 1 1 d . . . . .
N3 N 0.78470(7) 0.57289(11) 0.32562(18) 0.0163(3) Uani 1 1 d . . . . .
H7 H 0.7391 0.6046 0.3302 0.020 Uiso 1 1 calc R U . . .
C1 C 0.61009(9) 0.48926(12) -0.2603(2) 0.0144(3) Uani 1 1 d . . . . .
H6 H 0.6431 0.4342 -0.2032 0.017 Uiso 1 1 calc R U . . .
C2 C 0.62354(9) 0.54350(13) -0.4008(2) 0.0152(3) Uani 1 1 d . . . . .
H5 H 0.6669 0.5338 -0.4590 0.018 Uiso 1 1 calc R U . . .
C3 C 0.55199(10) 0.69910(12) -0.5727(2) 0.0168(3) Uani 1 1 d . . . . .
H3A H 0.4975 0.7257 -0.5908 0.025 Uiso 1 1 calc R U . . .
H3B H 0.5641 0.6679 -0.6777 0.025 Uiso 1 1 calc R U . . .
H3C H 0.5880 0.7600 -0.5374 0.025 Uiso 1 1 calc R U . . .
C4 C 0.51346(9) 0.60246(12) -0.32747(19) 0.0130(3) Uani 1 1 d . . . . .
H4 H 0.4660 0.6422 -0.3276 0.016 Uiso 1 1 calc R U . . .
C5 C 0.64410(8) 0.46039(12) 0.15437(18) 0.0115(3) Uani 1 1 d . . . . .
C6 C 0.71663(8) 0.40305(12) 0.24032(19) 0.0128(3) Uani 1 1 d . . . . .
C7 C 0.78427(9) 0.45929(13) 0.32268(19) 0.0139(3) Uani 1 1 d . . . . .
C8 C 0.84915(9) 0.64300(13) 0.32211(19) 0.0149(3) Uani 1 1 d . . . . .
C9 C 0.92123(9) 0.60851(13) 0.2818(2) 0.0187(3) Uani 1 1 d . . . . .
H13 H 0.9302 0.5331 0.2648 0.022 Uiso 1 1 calc R U . . .
C10 C 0.97969(9) 0.68383(14) 0.2667(2) 0.0213(3) Uani 1 1 d . . . . .
H12 H 1.0289 0.6594 0.2412 0.026 Uiso 1 1 calc R U . . .
C11 C 0.96739(10) 0.79423(14) 0.2882(2) 0.0223(4) Uani 1 1 d . . . . .
H11 H 1.0071 0.8461 0.2755 0.027 Uiso 1 1 calc R U . . .
C12 C 0.89574(10) 0.82710(13) 0.3287(2) 0.0191(3) Uani 1 1 d . . . . .
C13 C 0.83586(9) 0.75494(13) 0.35094(19) 0.0154(3) Uani 1 1 d . . . . .
C14 C 0.75866(10) 0.79026(13) 0.3986(2) 0.0197(3) Uani 1 1 d . . . . .
H8 H 0.7455 0.7426 0.4879 0.030 Uiso 1 1 calc R U . . .
H9 H 0.7171 0.7854 0.2998 0.030 Uiso 1 1 calc R U . . .
H10 H 0.7630 0.8658 0.4392 0.030 Uiso 1 1 calc R U . . .
C15 C 0.84718(9) 0.39784(14) 0.4097(2) 0.0177(3) Uani 1 1 d . . . . .
H17 H 0.8921 0.4344 0.4687 0.021 Uiso 1 1 calc R U . . .
C16 C 0.84454(9) 0.28538(14) 0.4105(2) 0.0194(3) Uani 1 1 d . . . . .
H16 H 0.8877 0.2455 0.4700 0.023 Uiso 1 1 calc R U . . .
C17 C 0.77951(10) 0.22936(13) 0.3253(2) 0.0205(3) Uani 1 1 d . . . . .
H14 H 0.7786 0.1518 0.3242 0.025 Uiso 1 1 calc R U . . .
C18 C 0.71627(9) 0.28858(13) 0.2425(2) 0.0164(3) Uani 1 1 d . . . . .
H15 H 0.6715 0.2507 0.1856 0.020 Uiso 1 1 calc R U . . .
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'
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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 '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
O1 Cu1 O1 180.00(4) . 3_665
O1 Cu1 N1 89.70(5) . 3_665
O1 Cu1 N1 90.30(5) 3_665 3_665
O1 Cu1 N1 90.30(5) . .
O1 Cu1 N1 89.70(5) 3_665 .
N1 Cu1 N1 180.0 3_665 .
C5 O1 Cu1 105.78(9) . .
C4 N1 C1 105.63(13) . .
C4 N1 Cu1 125.02(10) . .
C1 N1 Cu1 128.22(10) . .
C4 N2 C2 107.58(13) . .
C4 N2 C3 124.48(13) . .
C2 N2 C3 127.67(13) . .
C7 N3 C8 127.78(13) . .
C7 N3 H7 116.1 . .
C8 N3 H7 116.1 . .
C2 C1 N1 109.33(13) . .
C2 C1 H6 125.3 . .
N1 C1 H6 125.3 . .
C1 C2 N2 106.21(13) . .
C1 C2 H5 126.9 . .
N2 C2 H5 126.9 . .
N2 C3 H3A 109.5 . .
N2 C3 H3B 109.5 . .
H3A C3 H3B 109.5 . .
N2 C3 H3C 109.5 . .
H3A C3 H3C 109.5 . .
H3B C3 H3C 109.5 . .
N1 C4 N2 111.24(13) . .
N1 C4 H4 124.4 . .
N2 C4 H4 124.4 . .
O2 C5 O1 121.58(13) . .
O2 C5 C6 121.46(13) . .
O1 C5 C6 116.94(13) . .
C18 C6 C7 118.98(14) . .
C18 C6 C5 118.00(13) . .
C7 C6 C5 123.00(14) . .
N3 C7 C15 121.67(14) . .
N3 C7 C6 119.67(13) . .
C15 C7 C6 118.51(14) . .
C9 C8 N3 123.48(14) . .
C9 C8 C13 120.28(14) . .
N3 C8 C13 116.11(14) . .
C10 C9 C8 120.19(15) . .
C10 C9 H13 119.9 . .
C8 C9 H13 119.9 . .
C9 C10 C11 120.85(15) . .
C9 C10 H12 119.6 . .
C11 C10 H12 119.6 . .
C12 C11 C10 118.27(15) . .
C12 C11 H11 120.9 . .
C10 C11 H11 120.9 . .
C11 C12 C13 123.42(15) . .
C11 C12 Cl1 116.98(13) . .
C13 C12 Cl1 119.60(13) . .
C12 C13 C8 116.91(14) . .
C12 C13 C14 123.52(15) . .
C8 C13 C14 119.55(14) . .
C13 C14 H8 109.5 . .
C13 C14 H9 109.5 . .
H8 C14 H9 109.5 . .
C13 C14 H10 109.5 . .
H8 C14 H10 109.5 . .
H9 C14 H10 109.5 . .
C16 C15 C7 120.92(15) . .
C16 C15 H17 119.5 . .
C7 C15 H17 119.5 . .
C15 C16 C17 120.97(15) . .
C15 C16 H16 119.5 . .
C17 C16 H16 119.5 . .
C18 C17 C16 118.88(15) . .
C18 C17 H14 120.6 . .
C16 C17 H14 120.6 . .
C17 C18 C6 121.69(15) . .
C17 C18 H15 119.2 . .
C6 C18 H15 119.2 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cu1 O1 1.9703(10) .
Cu1 O1 1.9703(10) 3_665
Cu1 N1 1.9865(13) 3_665
Cu1 N1 1.9866(13) .
Cl1 C12 1.7512(17) .
O1 C5 1.2842(18) .
O2 C5 1.2547(18) .
N1 C4 1.3316(19) .
N1 C1 1.3827(19) .
N2 C4 1.3387(19) .
N2 C2 1.3781(19) .
N2 C3 1.4624(19) .
N3 C7 1.391(2) .
N3 C8 1.4050(19) .
N3 H7 0.8800 .
C1 C2 1.362(2) .
C1 H6 0.9500 .
C2 H5 0.9500 .
C3 H3A 0.9800 .
C3 H3B 0.9800 .
C3 H3C 0.9800 .
C4 H4 0.9500 .
C5 C6 1.498(2) .
C6 C18 1.402(2) .
C6 C7 1.419(2) .
C7 C15 1.407(2) .
C8 C9 1.395(2) .
C8 C13 1.415(2) .
C9 C10 1.383(2) .
C9 H13 0.9500 .
C10 C11 1.383(2) .
C10 H12 0.9500 .
C11 C12 1.383(2) .
C11 H11 0.9500 .
C12 C13 1.389(2) .
C13 C14 1.502(2) .
C14 H8 0.9800 .
C14 H9 0.9800 .
C14 H10 0.9800 .
C15 C16 1.378(2) .
C15 H17 0.9500 .
C16 C17 1.393(2) .
C16 H16 0.9500 .
C17 C18 1.384(2) .
C17 H14 0.9500 .
C18 H15 0.9500 .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N3 H7 O2 0.88 2.10 2.6630(16) 121.3 .
C3 H3A O1 0.98 2.62 3.4505(19) 143.1 2_654
N3 H7 O2 0.88 2.10 2.6630(16) 121.3 .
C3 H3A O1 0.98 2.62 3.4505(19) 143.1 2_654
C3 H3B O2 0.98 2.33 3.2396(19) 154.4 1_554
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
C4 N1 C1 C2 0.36(17) . . . .
Cu1 N1 C1 C2 -167.85(11) . . . .
N1 C1 C2 N2 -0.11(17) . . . .
C4 N2 C2 C1 -0.19(17) . . . .
C3 N2 C2 C1 173.94(14) . . . .
C1 N1 C4 N2 -0.49(16) . . . .
Cu1 N1 C4 N2 168.21(10) . . . .
C2 N2 C4 N1 0.43(17) . . . .
C3 N2 C4 N1 -173.93(13) . . . .
Cu1 O1 C5 O2 -4.13(17) . . . .
Cu1 O1 C5 C6 174.26(10) . . . .
O2 C5 C6 C18 172.56(14) . . . .
O1 C5 C6 C18 -5.8(2) . . . .
O2 C5 C6 C7 -5.8(2) . . . .
O1 C5 C6 C7 175.84(14) . . . .
C8 N3 C7 C15 38.1(2) . . . .
C8 N3 C7 C6 -146.46(16) . . . .
C18 C6 C7 N3 -178.26(14) . . . .
C5 C6 C7 N3 0.1(2) . . . .
C18 C6 C7 C15 -2.7(2) . . . .
C5 C6 C7 C15 175.62(14) . . . .
C7 N3 C8 C9 13.1(3) . . . .
C7 N3 C8 C13 -171.16(15) . . . .
N3 C8 C9 C10 174.39(15) . . . .
C13 C8 C9 C10 -1.2(2) . . . .
C8 C9 C10 C11 -1.1(3) . . . .
C9 C10 C11 C12 1.3(3) . . . .
C10 C11 C12 C13 0.8(3) . . . .
C10 C11 C12 Cl1 -178.63(14) . . . .
C11 C12 C13 C8 -3.0(2) . . . .
Cl1 C12 C13 C8 176.41(12) . . . .
C11 C12 C13 C14 178.63(16) . . . .
Cl1 C12 C13 C14 -2.0(2) . . . .
C9 C8 C13 C12 3.2(2) . . . .
N3 C8 C13 C12 -172.76(14) . . . .
C9 C8 C13 C14 -178.41(15) . . . .
N3 C8 C13 C14 5.7(2) . . . .
N3 C7 C15 C16 177.62(15) . . . .
C6 C7 C15 C16 2.1(2) . . . .
C7 C15 C16 C17 -0.1(3) . . . .
C15 C16 C17 C18 -1.5(3) . . . .
C16 C17 C18 C6 0.9(3) . . . .
C7 C6 C18 C17 1.2(2) . . . .
C5 C6 C18 C17 -177.18(15) . . . .
