#------------------------------------------------------------------------------
#$Date: 2021-07-07 12:29:37 +0300 (Wed, 07 Jul 2021) $
#$Revision: 267340 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/40/1564013.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_1564013
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         'C38 H40 Cu N6 O4, H2 O'
_chemical_formula_sum            'C38 H42 Cu N6 O5'
_chemical_formula_weight         726.31
_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     direct
_cell_angle_alpha                94.595(5)
_cell_angle_beta                 98.726(5)
_cell_angle_gamma                92.552(5)
_cell_formula_units_Z            1
_cell_length_a                   7.7814(9)
_cell_length_b                   7.8017(8)
_cell_length_c                   14.9217(16)
_cell_measurement_reflns_used    9906
_cell_measurement_temperature    99.95
_cell_measurement_theta_max      28.31
_cell_measurement_theta_min      2.62
_cell_volume                     891.03(17)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS-1997 (Sheldrick, 2008)'
_diffrn_ambient_temperature      99.95
_diffrn_measured_fraction_theta_full 0.974
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0200
_diffrn_reflns_av_unetI/netI     0.0163
_diffrn_reflns_Laue_measured_fraction_full 0.974
_diffrn_reflns_Laue_measured_fraction_max 0.971
_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       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            15756
_diffrn_reflns_point_group_measured_fraction_full 0.974
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.315
_diffrn_reflns_theta_min         1.386
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.665
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6321
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.1199 before and 0.0281 after correction.
The Ratio of minimum to maximum transmission is 0.8477.
The λ/2 correction factor is 0.0015.
;
_exptl_crystal_colour            blue
_exptl_crystal_colour_lustre     .
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    blue
_exptl_crystal_density_diffrn    1.354
_exptl_crystal_density_meas      .
_exptl_crystal_description       block
_exptl_crystal_F_000             381
_exptl_crystal_size_max          0.78
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.596
_refine_diff_density_min         -0.591
_refine_diff_density_rms         0.073
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     239
_refine_ls_number_reflns         4322
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0370
_refine_ls_R_factor_gt           0.0363
_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)+(0.0635P)²+0.7987P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1089
_refine_ls_wR_factor_ref         0.1094
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4190
_reflns_number_total             4322
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            mo_pa_ns_143_a_0m.cif
_cod_data_source_block           mo_pa_ns_143_a_0m
_cod_database_code               1564013
_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.
;
_shelx_estimated_absorpt_t_max   0.825
_shelx_estimated_absorpt_t_min   0.625
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H,H) groups
2. Others
 Fixed Sof: O3(0.5) H3B(0.5) H3C(0.5)
3.a Free rotating group:
 O3(H3B,H3C)
3.b Me refined with riding coordinates:
 C18(H18A,H18B,H18C), C19(H19A,H19B,H19C), C17(H17A,H17B,H17C)
3.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C9(H9), C11(H11), C3(H3A), C2(H2), C10(H10), C14(H14), C8(H8),
 C16(H16), C15(H15)
;
_olex2_submission_special_instructions 'No special instructions were received'
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
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.500000 0.500000 0.000000 0.01515(10) Uani 1 2 d S T P . .
O1 O 0.53720(17) 0.50640(17) 0.13348(8) 0.0209(3) Uani 1 1 d . . . . .
O2 O 0.43893(18) 0.76459(19) 0.11306(8) 0.0245(3) Uani 1 1 d . . . . .
N3 N 0.3339(2) 0.93299(18) 0.25639(10) 0.0176(3) Uani 1 1 d . . . . .
C13 C 0.4952(2) 0.6539(2) 0.16429(11) 0.0174(3) Uani 1 1 d . . . . .
N1 N 0.73737(19) 0.6112(2) 0.00550(10) 0.0203(3) Uani 1 1 d . . . . .
C12 C 0.5138(2) 0.6865(2) 0.26536(10) 0.0137(3) Uani 1 1 d . . . . .
C1 C 0.3003(2) 1.2359(2) 0.29363(11) 0.0174(3) Uani 1 1 d . . . . .
H1 H 0.404799 1.261747 0.270564 0.021 Uiso 1 1 calc R . . . .
N2 N 0.9694(2) 0.7368(2) -0.03645(12) 0.0244(3) Uani 1 1 d . . . . .
C9 C 0.5446(2) 0.7267(2) 0.45497(11) 0.0174(3) Uani 1 1 d . . . . .
H9 H 0.553383 0.739525 0.519382 0.021 Uiso 1 1 calc R . . . .
C11 C 0.6155(2) 0.5789(2) 0.31979(11) 0.0147(3) Uani 1 1 d . . . . .
H11 H 0.673791 0.490129 0.291488 0.018 Uiso 1 1 calc R . . . .
C5 C 0.0855(2) 1.0235(2) 0.32839(11) 0.0178(3) Uani 1 1 d . . . . .
C4 C -0.0062(2) 1.1577(2) 0.36367(12) 0.0202(3) Uani 1 1 d . . . . .
C3 C 0.0559(2) 1.3283(2) 0.36225(12) 0.0204(3) Uani 1 1 d . . . . .
H3A H -0.006520 1.419053 0.385775 0.024 Uiso 1 1 calc R . . . .
C7 C 0.4295(2) 0.82024(19) 0.30755(10) 0.0136(3) Uani 1 1 d . . . . .
C2 C 0.2073(2) 1.3680(2) 0.32705(12) 0.0201(3) Uani 1 1 d . . . . .
H2 H 0.246715 1.484681 0.325934 0.024 Uiso 1 1 calc R . . . .
C10 C 0.6332(2) 0.5989(2) 0.41388(11) 0.0167(3) Uani 1 1 d . . . . .
H10 H 0.704632 0.526458 0.449823 0.020 Uiso 1 1 calc R . . . .
C14 C 0.8655(2) 0.6456(3) 0.08081(13) 0.0249(4) Uani 1 1 d . . . . .
H14 H 0.855115 0.619809 0.140967 0.030 Uiso 1 1 calc R . . . .
C8 C 0.4440(2) 0.8351(2) 0.40294(11) 0.0160(3) Uani 1 1 d . . . . .
H8 H 0.383652 0.921000 0.432119 0.019 Uiso 1 1 calc R . . . .
C6 C 0.2394(2) 1.0646(2) 0.29406(11) 0.0154(3) Uani 1 1 d . . . . .
C16 C 0.8054(2) 0.6687(2) -0.06356(13) 0.0231(3) Uani 1 1 d . . . . .
H16 H 0.746171 0.662610 -0.124384 0.028 Uiso 1 1 calc R . . . .
C15 C 1.0087(2) 0.7224(3) 0.05511(14) 0.0273(4) Uani 1 1 d . . . . .
H15 H 1.115268 0.758805 0.093302 0.033 Uiso 1 1 calc R . . . .
C18 C 0.0154(3) 0.8392(2) 0.32629(14) 0.0260(4) Uani 1 1 d . . . . .
H18A H 0.094007 0.761893 0.299892 0.039 Uiso 1 1 calc R . . . .
H18B H 0.007209 0.811138 0.388414 0.039 Uiso 1 1 calc R . . . .
H18C H -0.100369 0.824978 0.289217 0.039 Uiso 1 1 calc R . . . .
C19 C -0.1723(3) 1.1184(3) 0.40086(17) 0.0328(4) Uani 1 1 d . . . . .
H19A H -0.196417 0.993432 0.396707 0.049 Uiso 1 1 calc R . . . .
H19B H -0.159298 1.164923 0.464664 0.049 Uiso 1 1 calc R . . . .
H19C H -0.269066 1.171430 0.365327 0.049 Uiso 1 1 calc R . . . .
C17 C 1.0866(3) 0.8071(3) -0.09480(16) 0.0334(4) Uani 1 1 d . . . . .
H17A H 1.197770 0.848018 -0.057501 0.050 Uiso 1 1 calc R . . . .
H17B H 1.107048 0.716797 -0.140932 0.050 Uiso 1 1 calc R . . . .
H17C H 1.033255 0.903134 -0.124830 0.050 Uiso 1 1 calc R . . . .
O3 O 0.4665(8) 1.0746(5) 0.0499(3) 0.0685(14) Uani 0.5 1 d . . . A -1
H3B H 0.491197 1.106694 -0.001453 0.103 Uiso 0.5 1 d G . . A -1
H3C H 0.489829 0.967236 0.054142 0.103 Uiso 0.5 1 d G . . A -1
H3 H 0.355(3) 0.940(3) 0.2050(17) 0.021(5) 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
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'
Cu Cu 0.3201 1.2651 '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
O1 Cu1 O1 180.0 . 2_665
O1 Cu1 N1 89.63(6) 2_665 2_665
O1 Cu1 N1 89.63(6) . .
O1 Cu1 N1 90.37(6) . 2_665
O1 Cu1 N1 90.37(6) 2_665 .
N1 Cu1 N1 180.0 2_665 .
C13 O1 Cu1 107.54(11) . .
C7 N3 C6 123.71(14) . .
C7 N3 H3 116.0(17) . .
C6 N3 H3 118.1(17) . .
O1 C13 C12 116.47(15) . .
O2 C13 O1 122.20(15) . .
O2 C13 C12 121.32(15) . .
C14 N1 Cu1 128.01(13) . .
C16 N1 Cu1 126.56(12) . .
C16 N1 C14 105.42(16) . .
C11 C12 C13 118.80(14) . .
C11 C12 C7 119.18(14) . .
C7 C12 C13 122.01(14) . .
C2 C1 H1 120.1 . .
C2 C1 C6 119.74(16) . .
C6 C1 H1 120.1 . .
C16 N2 C15 107.14(16) . .
C16 N2 C17 126.54(17) . .
C15 N2 C17 126.27(17) . .
C10 C9 H9 119.7 . .
C8 C9 H9 119.7 . .
C8 C9 C10 120.61(15) . .
C12 C11 H11 119.2 . .
C10 C11 C12 121.55(15) . .
C10 C11 H11 119.2 . .
C4 C5 C6 118.91(15) . .
C4 C5 C18 119.63(16) . .
C6 C5 C18 121.46(16) . .
C5 C4 C19 120.37(16) . .
C3 C4 C5 119.34(16) . .
C3 C4 C19 120.28(17) . .
C4 C3 H3A 119.3 . .
C2 C3 C4 121.36(16) . .
C2 C3 H3A 119.3 . .
N3 C7 C12 120.86(14) . .
N3 C7 C8 120.63(15) . .
C8 C7 C12 118.50(14) . .
C1 C2 C3 119.59(15) . .
C1 C2 H2 120.2 . .
C3 C2 H2 120.2 . .
C9 C10 H10 120.5 . .
C11 C10 C9 119.02(15) . .
C11 C10 H10 120.5 . .
N1 C14 H14 125.3 . .
C15 C14 N1 109.31(17) . .
C15 C14 H14 125.3 . .
C9 C8 C7 121.05(15) . .
C9 C8 H8 119.5 . .
C7 C8 H8 119.5 . .
C1 C6 N3 118.33(15) . .
C1 C6 C5 121.05(15) . .
C5 C6 N3 120.59(14) . .
N1 C16 N2 111.45(16) . .
N1 C16 H16 124.3 . .
N2 C16 H16 124.3 . .
N2 C15 H15 126.7 . .
C14 C15 N2 106.67(16) . .
C14 C15 H15 126.7 . .
C5 C18 H18A 109.5 . .
C5 C18 H18B 109.5 . .
C5 C18 H18C 109.5 . .
H18A C18 H18B 109.5 . .
H18A C18 H18C 109.5 . .
H18B C18 H18C 109.5 . .
C4 C19 H19A 109.5 . .
C4 C19 H19B 109.5 . .
C4 C19 H19C 109.5 . .
H19A C19 H19B 109.5 . .
H19A C19 H19C 109.5 . .
H19B C19 H19C 109.5 . .
N2 C17 H17A 109.5 . .
N2 C17 H17B 109.5 . .
N2 C17 H17C 109.5 . .
H17A C17 H17B 109.5 . .
H17A C17 H17C 109.5 . .
H17B C17 H17C 109.5 . .
H3B O3 H3C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cu1 O1 1.9650(12) .
Cu1 O1 1.9650(12) 2_665
Cu1 N1 1.9927(16) 2_665
Cu1 N1 1.9927(16) .
O1 C13 1.280(2) .
O2 C13 1.249(2) .
N3 C7 1.380(2) .
N3 C6 1.418(2) .
N3 H3 0.81(3) .
C13 C12 1.493(2) .
N1 C14 1.384(2) .
N1 C16 1.327(2) .
C12 C11 1.402(2) .
C12 C7 1.412(2) .
C1 H1 0.9500 .
C1 C2 1.388(2) .
C1 C6 1.399(2) .
N2 C16 1.350(2) .
N2 C15 1.369(3) .
N2 C17 1.471(3) .
C9 H9 0.9500 .
C9 C10 1.391(2) .
C9 C8 1.382(2) .
C11 H11 0.9500 .
C11 C10 1.385(2) .
C5 C4 1.406(2) .
C5 C6 1.406(2) .
C5 C18 1.511(2) .
C4 C3 1.398(2) .
C4 C19 1.511(3) .
C3 H3A 0.9500 .
C3 C2 1.393(3) .
C7 C8 1.406(2) .
C2 H2 0.9500 .
C10 H10 0.9500 .
C14 H14 0.9500 .
C14 C15 1.362(3) .
C8 H8 0.9500 .
C16 H16 0.9500 .
C15 H15 0.9500 .
C18 H18A 0.9800 .
C18 H18B 0.9800 .
C18 H18C 0.9800 .
C19 H19A 0.9800 .
C19 H19B 0.9800 .
C19 H19C 0.9800 .
C17 H17A 0.9800 .
C17 H17B 0.9800 .
C17 H17C 0.9800 .
O3 H3B 0.8703 .
O3 H3C 0.8699 .
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
_geom_hbond_publ_flag
O3 H3C O2 0.87 1.92 2.676(4) 143.9 . yes
N3 H3 O2 0.81(3) 2.05(2) 2.6730(19) 132(2) . yes
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
Cu1 O1 C13 O2 1.1(2) . . . .
Cu1 O1 C13 C12 -179.98(11) . . . .
Cu1 N1 C14 C15 179.82(13) . . . .
Cu1 N1 C16 N2 -179.95(12) . . . .
O1 C13 C12 C11 16.6(2) . . . .
O1 C13 C12 C7 -162.27(15) . . . .
O2 C13 C12 C11 -164.49(15) . . . .
O2 C13 C12 C7 16.7(2) . . . .
N3 C7 C8 C9 -177.66(15) . . . .
C13 C12 C11 C10 -177.83(14) . . . .
C13 C12 C7 N3 -3.7(2) . . . .
C13 C12 C7 C8 175.70(14) . . . .
N1 C14 C15 N2 0.4(2) . . . .
C12 C11 C10 C9 1.4(2) . . . .
C12 C7 C8 C9 2.9(2) . . . .
C11 C12 C7 N3 177.44(14) . . . .
C11 C12 C7 C8 -3.1(2) . . . .
C5 C4 C3 C2 -0.4(3) . . . .
C4 C5 C6 N3 -178.86(15) . . . .
C4 C5 C6 C1 -0.8(2) . . . .
C4 C3 C2 C1 -0.8(3) . . . .
C7 N3 C6 C1 109.92(18) . . . .
C7 N3 C6 C5 -72.0(2) . . . .
C7 C12 C11 C10 1.0(2) . . . .
C2 C1 C6 N3 177.73(15) . . . .
C2 C1 C6 C5 -0.4(2) . . . .
C10 C9 C8 C7 -0.5(3) . . . .
C14 N1 C16 N2 0.3(2) . . . .
C8 C9 C10 C11 -1.6(2) . . . .
C6 N3 C7 C12 176.84(14) . . . .
C6 N3 C7 C8 -2.6(2) . . . .
C6 C1 C2 C3 1.2(3) . . . .
C6 C5 C4 C3 1.1(3) . . . .
C6 C5 C4 C19 179.79(17) . . . .
C16 N1 C14 C15 -0.4(2) . . . .
C16 N2 C15 C14 -0.2(2) . . . .
C15 N2 C16 N1 0.0(2) . . . .
C18 C5 C4 C3 -177.59(17) . . . .
C18 C5 C4 C19 1.1(3) . . . .
C18 C5 C6 N3 -0.1(2) . . . .
C18 C5 C6 C1 177.94(16) . . . .
C19 C4 C3 C2 -179.02(18) . . . .
C17 N2 C16 N1 177.68(17) . . . .
C17 N2 C15 C14 -177.94(18) . . . .
