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#$Date: 2023-05-05 05:53:27 +0300 (Fri, 05 May 2023) $
#$Revision: 283383 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/06/23/7062374.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_7062374
loop_
_publ_author_name
'Gurbanov, Atash V.'
'Mahmoud, Abdallah G.'
'Aliyeva, Vusala A.'
'Guedes da Silva, M. Fátima C.'
'Pombeiro, Armando J. L.'
_publ_section_title
;
 Novel cyano-activated Cu(ii) complexes of arylhydrazones of active
 methylene nitriles and their catalytic application for azide--alkyne
 cycloaddition in water and glycerol
;
_journal_issue                   17
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              7965
_journal_page_last               7974
_journal_paper_doi               10.1039/D3NJ00512G
_journal_volume                  47
_journal_year                    2023
_chemical_formula_moiety         'C24 H24 Cu2 N8 O8'
_chemical_formula_sum            'C24 H24 Cu2 N8 O8'
_chemical_formula_weight         679.59
_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
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2019/1
_audit_update_record
;
2023-01-05 deposited with the CCDC.	2023-03-14 downloaded from the CCDC.
;
_cell_angle_alpha                60.556(6)
_cell_angle_beta                 76.213(6)
_cell_angle_gamma                68.001(7)
_cell_formula_units_Z            1
_cell_length_a                   9.3312(17)
_cell_length_b                   9.3618(19)
_cell_length_c                   9.4050(15)
_cell_measurement_reflns_used    6770
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      26.50
_cell_measurement_theta_min      2.36
_cell_volume                     661.9(2)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_structure_solution    'SHELXT 2019/1 (Sheldrick, 2019)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Bruker D8 Quest PHOTON 100 detector'
_diffrn_measurement_method       'φ 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     0.0383
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            14352
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.571
_diffrn_reflns_theta_min         2.874
_exptl_absorpt_coefficient_mu    1.672
_exptl_absorpt_correction_T_max  0.703
_exptl_absorpt_correction_T_min  0.654
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2008)'
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.705
_exptl_crystal_description       block
_exptl_crystal_F_000             346
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.361
_refine_diff_density_min         -0.320
_refine_diff_density_rms         0.068
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         2728
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0325
_refine_ls_R_factor_gt           0.0274
_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)+(0.0239P)²+0.5617P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0675
_refine_ls_wR_factor_ref         0.0698
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2446
_reflns_number_total             2728
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3nj00512g2.cif
_cod_data_source_block           PA86_A
_cod_depositor_comments
'Adding full bibliography for 7062374--7062378.cif.'
_cod_database_code               7062374
_shelx_shelxl_version_number     2019/1
_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_min   0.680
_shelx_estimated_absorpt_t_max   0.731
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 0.11828(3) 0.57885(3) 0.51324(3) 0.01451(9) Uani 1 1 d . . . . .
O1 O -0.0105(2) 0.3973(2) 0.89092(19) 0.0255(4) Uani 1 1 d . . . . .
O2 O -0.01938(17) 0.41393(19) 0.64972(17) 0.0165(3) Uani 1 1 d . . . . .
O3 O 0.41143(18) 0.5105(2) 0.82579(18) 0.0207(3) Uani 1 1 d . . . . .
O4 O -0.07974(18) 0.7993(2) 0.54286(18) 0.0192(3) Uani 1 1 d . . . . .
H4O H -0.165227 0.779834 0.556740 0.029 Uiso 1 1 d R U . . .
N1 N 0.2270(2) 0.5114(2) 0.6958(2) 0.0183(4) Uani 1 1 d . . . . .
H1N H 0.177694 0.452986 0.789586 0.022 Uiso 1 1 d R U . . .
N2 N 0.3700(2) 0.7335(2) 0.3927(2) 0.0163(4) Uani 1 1 d . . . . .
N3 N 0.2566(2) 0.7098(2) 0.3557(2) 0.0148(3) Uani 1 1 d . . . . .
N4 N 0.6412(3) 0.7401(3) 0.5628(3) 0.0314(5) Uani 1 1 d . . . . .
C1 C 0.3414(2) 0.5559(3) 0.6951(3) 0.0159(4) Uani 1 1 d . . . . .
C2 C 0.4089(2) 0.6660(3) 0.5440(3) 0.0175(4) Uani 1 1 d . . . . .
C3 C 0.5385(3) 0.7081(3) 0.5541(3) 0.0211(5) Uani 1 1 d . . . . .
C4 C 0.2392(2) 0.8008(3) 0.1833(2) 0.0147(4) Uani 1 1 d . . . . .
C5 C 0.3108(3) 0.9296(3) 0.0831(3) 0.0192(4) Uani 1 1 d . . . . .
H5 H 0.365349 0.959857 0.132255 0.023 Uiso 1 1 calc R U . . .
C6 C 0.3039(3) 1.0135(3) -0.0852(3) 0.0231(5) Uani 1 1 d . . . . .
H6 H 0.353398 1.100106 -0.150041 0.028 Uiso 1 1 calc R U . . .
C7 C -0.2250(3) 0.0289(3) 1.1590(3) 0.0256(5) Uani 1 1 d . . . . .
H7 H -0.222328 -0.025465 1.274649 0.031 Uiso 1 1 calc R U . . .
C8 C -0.1502(3) 0.1512(3) 1.0617(3) 0.0221(5) Uani 1 1 d . . . . .
H8 H -0.094814 0.178868 1.112586 0.027 Uiso 1 1 calc R U . . .
C9 C -0.1526(2) 0.2365(3) 0.8904(3) 0.0165(4) Uani 1 1 d . . . . .
C10 C -0.0571(2) 0.3577(3) 0.8075(2) 0.0163(4) Uani 1 1 d . . . . .
C11 C 0.3562(3) 0.3969(3) 0.9842(3) 0.0242(5) Uani 1 1 d . . . . .
H11A H 0.416280 0.374267 1.069401 0.036 Uiso 1 1 calc R U . . .
H11B H 0.368454 0.288046 0.984525 0.036 Uiso 1 1 calc R U . . .
H11C H 0.246508 0.451469 1.005589 0.036 Uiso 1 1 calc R U . . .
C12 C -0.0885(3) 0.8456(3) 0.6687(3) 0.0309(6) Uani 1 1 d . . . . .
H12A H -0.191038 0.926278 0.673957 0.046 Uiso 1 1 calc R U . . .
H12B H -0.008766 0.900413 0.644776 0.046 Uiso 1 1 calc R U . . .
H12C H -0.071869 0.742133 0.773928 0.046 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'
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
_geom_angle_publ_flag
N1 Cu1 O2 165.75(7) . 2_566 ?
N1 Cu1 N3 92.80(7) . . ?
O2 Cu1 N3 95.25(7) 2_566 . ?
N1 Cu1 O2 94.62(7) . . ?
O2 Cu1 O2 75.65(6) 2_566 . ?
N3 Cu1 O2 168.02(6) . . ?
N1 Cu1 O4 96.73(7) . . ?
O2 Cu1 O4 93.57(6) 2_566 . ?
N3 Cu1 O4 99.18(7) . . ?
O2 Cu1 O4 89.28(6) . . ?
C10 O2 Cu1 128.06(13) . 2_566 ?
C10 O2 Cu1 125.51(12) . . ?
Cu1 O2 Cu1 104.35(6) 2_566 . ?
C1 O3 C11 117.54(16) . . ?
C12 O4 Cu1 122.49(14) . . ?
C12 O4 H4O 103.8 . . ?
Cu1 O4 H4O 109.3 . . ?
C1 N1 Cu1 127.85(16) . . ?
C1 N1 H1N 121.8 . . ?
Cu1 N1 H1N 109.8 . . ?
N3 N2 C2 123.44(17) . . ?
N2 N3 C4 111.11(16) . . ?
N2 N3 Cu1 125.61(14) . . ?
C4 N3 Cu1 123.20(13) . . ?
N1 C1 O3 126.20(19) . . ?
N1 C1 C2 121.35(19) . . ?
O3 C1 C2 112.45(17) . . ?
N2 C2 C3 113.43(19) . . ?
N2 C2 C1 128.83(19) . . ?
C3 C2 C1 117.73(19) . . ?
N4 C3 C2 179.5(3) . . ?
C9 C4 C5 118.41(19) 2_566 . ?
C9 C4 N3 121.43(18) 2_566 . ?
C5 C4 N3 120.15(18) . . ?
C6 C5 C4 121.8(2) . . ?
C6 C5 H5 119.1 . . ?
C4 C5 H5 119.1 . . ?
C7 C6 C5 119.9(2) 2_566 . ?
C7 C6 H6 120.0 2_566 . ?
C5 C6 H6 120.0 . . ?
C8 C7 C6 118.9(2) . 2_566 ?
C8 C7 H7 120.6 . . ?
C6 C7 H7 120.6 2_566 . ?
C7 C8 C9 122.6(2) . . ?
C7 C8 H8 118.7 . . ?
C9 C8 H8 118.7 . . ?
C4 C9 C8 118.29(19) 2_566 . ?
C4 C9 C10 127.67(19) 2_566 . ?
C8 C9 C10 114.03(18) . . ?
O1 C10 O2 121.22(19) . . ?
O1 C10 C9 118.74(19) . . ?
O2 C10 C9 119.98(17) . . ?
O3 C11 H11A 109.5 . . ?
O3 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
O3 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O4 C12 H12A 109.5 . . ?
O4 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
O4 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 N1 1.9133(18) . ?
Cu1 O2 1.9316(14) 2_566 ?
Cu1 N3 1.9622(17) . ?
Cu1 O2 2.1055(14) . ?
Cu1 O4 2.2834(16) . ?
O1 C10 1.229(3) . ?
O2 C10 1.313(3) . ?
O3 C1 1.334(2) . ?
O3 C11 1.450(3) . ?
O4 C12 1.424(3) . ?
O4 H4O 0.8500 . ?
N1 C1 1.281(3) . ?
N1 H1N 0.9000 . ?
N2 N3 1.311(2) . ?
N2 C2 1.322(3) . ?
N3 C4 1.430(3) . ?
N4 C3 1.136(3) . ?
C1 C2 1.448(3) . ?
C2 C3 1.441(3) . ?
C4 C9 1.404(3) 2_566 ?
C4 C5 1.405(3) . ?
C5 C6 1.384(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.384(3) 2_566 ?
C6 H6 0.9500 . ?
C7 C8 1.378(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.405(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.498(3) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
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
O4 H4O N4 0.85 1.96 2.805(2) 173.5 1_455 yes
N1 H1N O1 0.90 1.91 2.707(2) 146.0 . 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
_geom_torsion_publ_flag
C2 N2 N3 C4 178.90(19) . . . . ?
C2 N2 N3 Cu1 2.2(3) . . . . ?
Cu1 N1 C1 O3 177.71(16) . . . . ?
Cu1 N1 C1 C2 -2.1(3) . . . . ?
C11 O3 C1 N1 1.5(3) . . . . ?
C11 O3 C1 C2 -178.63(19) . . . . ?
N3 N2 C2 C3 179.22(19) . . . . ?
N3 N2 C2 C1 0.6(4) . . . . ?
N1 C1 C2 N2 -0.7(4) . . . . ?
O3 C1 C2 N2 179.5(2) . . . . ?
N1 C1 C2 C3 -179.3(2) . . . . ?
O3 C1 C2 C3 0.9(3) . . . . ?
N2 N3 C4 C9 164.42(19) . . . 2_566 ?
Cu1 N3 C4 C9 -18.8(3) . . . 2_566 ?
N2 N3 C4 C5 -15.0(3) . . . . ?
Cu1 N3 C4 C5 161.81(16) . . . . ?
C9 C4 C5 C6 -3.1(3) 2_566 . . . ?
N3 C4 C5 C6 176.3(2) . . . . ?
C4 C5 C6 C7 0.0(4) . . . 2_566 ?
C6 C7 C8 C9 0.9(4) 2_566 . . . ?
C7 C8 C9 C4 2.2(4) . . . 2_566 ?
C7 C8 C9 C10 -176.9(2) . . . . ?
Cu1 O2 C10 O1 -162.12(16) 2_566 . . . ?
Cu1 O2 C10 O1 -1.2(3) . . . . ?
Cu1 O2 C10 C9 20.7(3) 2_566 . . . ?
Cu1 O2 C10 C9 -178.30(14) . . . . ?
C4 C9 C10 O1 167.6(2) 2_566 . . . ?
C8 C9 C10 O1 -13.3(3) . . . . ?
C4 C9 C10 O2 -15.2(3) 2_566 . . . ?
C8 C9 C10 O2 163.9(2) . . . . ?
