#------------------------------------------------------------------------------
#$Date: 2023-05-05 04:53:27 +0200 (Fri 05 de May de 2023) $
#$Revision: 283383 $
#$URL: svn://www.crystallography.net/cod/cif/7/06/23/7062377.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_7062377
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         'C16 H13 Cu N5 O3'
_chemical_formula_sum            'C16 H13 Cu N5 O3'
_chemical_formula_weight         386.85
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_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                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   7.5563(2)
_cell_length_b                   19.9231(4)
_cell_length_c                   19.9344(4)
_cell_measurement_reflns_used    9968
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      26.35
_cell_measurement_theta_min      3.06
_cell_volume                     3001.02(12)
_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 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0326
_diffrn_reflns_av_unetI/netI     0.0159
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            28483
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.374
_diffrn_reflns_theta_min         2.286
_exptl_absorpt_coefficient_mu    1.484
_exptl_absorpt_correction_T_max  0.802
_exptl_absorpt_correction_T_min  0.632
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2008)'
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.712
_exptl_crystal_description       plate
_exptl_crystal_F_000             1576
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.140
_refine_diff_density_max         0.311
_refine_diff_density_min         -0.454
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         3074
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.074
_refine_ls_R_factor_all          0.0309
_refine_ls_R_factor_gt           0.0249
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0371P)²+1.6377P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0659
_refine_ls_wR_factor_ref         0.0695
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2692
_reflns_number_total             3074
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3nj00512g2.cif
_cod_data_source_block           5c_a
_cod_depositor_comments
'Adding full bibliography for 7062374--7062378.cif.'
_cod_database_code               7062377
_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   0.648
_shelx_estimated_absorpt_t_max   0.819
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'
'-x, -y, -z'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'
'x-1/2, y, -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 0.35669(3) 0.75250(2) 0.42096(2) 0.01684(8) Uani 1 1 d . . . . .
O1 O 0.24557(19) 0.68435(6) 0.47166(6) 0.0256(3) Uani 1 1 d . . . . .
O2 O 0.13127(18) 0.58795(6) 0.50161(6) 0.0252(3) Uani 1 1 d . . . . .
O3 O 0.69726(17) 0.86837(6) 0.30544(6) 0.0220(3) Uani 1 1 d . . . . .
N1 N 0.52694(19) 0.81825(7) 0.38977(7) 0.0182(3) Uani 1 1 d . . . . .
H1N H 0.564251 0.851181 0.418677 0.022 Uiso 1 1 d R U . . .
N2 N 0.45309(18) 0.71546(7) 0.28533(7) 0.0170(3) Uani 1 1 d . . . . .
N3 N 0.39734(19) 0.69347(7) 0.34344(7) 0.0158(3) Uani 1 1 d . . . . .
N4 N 0.6079(2) 0.80178(7) 0.15426(8) 0.0231(3) Uani 1 1 d . . . . .
N5 N 0.2909(2) 0.81503(7) 0.49749(7) 0.0190(3) Uani 1 1 d . . . . .
C1 C 0.5823(2) 0.82249(8) 0.32927(8) 0.0171(3) Uani 1 1 d . . . . .
C2 C 0.5289(2) 0.77502(8) 0.27747(8) 0.0167(3) Uani 1 1 d . . . . .
C3 C 0.3462(2) 0.62445(8) 0.33999(8) 0.0160(3) Uani 1 1 d . . . . .
C4 C 0.3987(2) 0.58552(8) 0.28434(8) 0.0191(3) Uani 1 1 d . . . . .
H4 H 0.468052 0.605500 0.249984 0.023 Uiso 1 1 calc R U . . .
C5 C 0.3508(2) 0.51884(9) 0.27900(9) 0.0219(4) Uani 1 1 d . . . . .
H5 H 0.388158 0.493547 0.241165 0.026 Uiso 1 1 calc R U . . .
C6 C 0.2485(3) 0.48824(9) 0.32831(9) 0.0232(4) Uani 1 1 d . . . . .
H6 H 0.211850 0.442863 0.323685 0.028 Uiso 1 1 calc R U . . .
C7 C 0.2013(2) 0.52524(8) 0.38420(9) 0.0209(4) Uani 1 1 d . . . . .
H7 H 0.132942 0.504423 0.418371 0.025 Uiso 1 1 calc R U . . .
C8 C 0.2513(2) 0.59271(8) 0.39193(8) 0.0169(3) Uani 1 1 d . . . . .
C9 C 0.2054(2) 0.62339(8) 0.45920(8) 0.0181(3) Uani 1 1 d . . . . .
C10 C 0.5738(2) 0.79031(8) 0.20934(9) 0.0183(3) Uani 1 1 d . . . . .
C11 C 0.7762(3) 0.91321(9) 0.35395(9) 0.0249(4) Uani 1 1 d . . . . .
H11A H 0.861265 0.942675 0.331349 0.037 Uiso 1 1 calc R U . . .
H11B H 0.837424 0.886910 0.388419 0.037 Uiso 1 1 calc R U . . .
H11C H 0.683573 0.940448 0.374974 0.037 Uiso 1 1 calc R U . . .
C12 C 0.3335(2) 0.79704(9) 0.56053(9) 0.0210(4) Uani 1 1 d . . . . .
H12 H 0.379641 0.753357 0.568199 0.025 Uiso 1 1 calc R U . . .
C13 C 0.3125(3) 0.83982(9) 0.61448(9) 0.0243(4) Uani 1 1 d . . . . .
H13 H 0.343892 0.825832 0.658453 0.029 Uiso 1 1 calc R U . . .
C14 C 0.2450(3) 0.90329(9) 0.60336(10) 0.0271(4) Uani 1 1 d . . . . .
H14 H 0.230012 0.933643 0.639672 0.033 Uiso 1 1 calc R U . . .
C15 C 0.1995(3) 0.92225(9) 0.53882(10) 0.0279(4) Uani 1 1 d . . . . .
H15 H 0.152155 0.965553 0.530072 0.033 Uiso 1 1 calc R U . . .
C16 C 0.2246(3) 0.87666(9) 0.48737(9) 0.0238(4) Uani 1 1 d . . . . .
H16 H 0.193557 0.889524 0.443018 0.029 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
O1 Cu1 N1 162.20(6) . . ?
O1 Cu1 N3 93.44(5) . . ?
N1 Cu1 N3 92.77(6) . . ?
O1 Cu1 N5 86.00(5) . . ?
N1 Cu1 N5 89.36(6) . . ?
N3 Cu1 N5 174.48(6) . . ?
C9 O1 Cu1 133.28(11) . . ?
C1 O3 C11 116.72(13) . . ?
C1 N1 Cu1 124.34(12) . . ?
C1 N1 H1N 116.4 . . ?
Cu1 N1 H1N 119.1 . . ?
N3 N2 C2 122.88(14) . . ?
N2 N3 C3 111.50(13) . . ?
N2 N3 Cu1 123.10(10) . . ?
C3 N3 Cu1 124.80(11) . . ?
C16 N5 C12 118.26(15) . . ?
C16 N5 Cu1 122.67(12) . . ?
C12 N5 Cu1 118.64(12) . . ?
N1 C1 O3 126.02(15) . . ?
N1 C1 C2 122.30(15) . . ?
O3 C1 C2 111.66(14) . . ?
N2 C2 C10 113.85(14) . . ?
N2 C2 C1 128.06(15) . . ?
C10 C2 C1 117.90(15) . . ?
C8 C3 C4 118.31(15) . . ?
C8 C3 N3 122.26(14) . . ?
C4 C3 N3 119.37(15) . . ?
C5 C4 C3 121.06(16) . . ?
C5 C4 H4 119.5 . . ?
C3 C4 H4 119.5 . . ?
C4 C5 C6 120.84(16) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C7 C6 C5 118.63(16) . . ?
C7 C6 H6 120.7 . . ?
C5 C6 H6 120.7 . . ?
C6 C7 C8 121.94(16) . . ?
C6 C7 H7 119.0 . . ?
C8 C7 H7 119.0 . . ?
C7 C8 C3 119.05(15) . . ?
C7 C8 C9 114.95(15) . . ?
C3 C8 C9 125.88(14) . . ?
O2 C9 O1 121.23(15) . . ?
O2 C9 C8 118.62(15) . . ?
O1 C9 C8 120.14(15) . . ?
N4 C10 C2 178.84(19) . . ?
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 . . ?
N5 C12 C13 122.35(16) . . ?
N5 C12 H12 118.8 . . ?
C13 C12 H12 118.8 . . ?
C14 C13 C12 118.84(17) . . ?
C14 C13 H13 120.6 . . ?
C12 C13 H13 120.6 . . ?
C13 C14 C15 119.38(17) . . ?
C13 C14 H14 120.3 . . ?
C15 C14 H14 120.3 . . ?
C16 C15 C14 118.41(17) . . ?
C16 C15 H15 120.8 . . ?
C14 C15 H15 120.8 . . ?
N5 C16 C15 122.75(17) . . ?
N5 C16 H16 118.6 . . ?
C15 C16 H16 118.6 . . ?
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 O1 1.8895(12) . ?
Cu1 N1 1.9384(14) . ?
Cu1 N3 1.9661(14) . ?
Cu1 N5 2.0314(14) . ?
O1 C9 1.276(2) . ?
O2 C9 1.236(2) . ?
O3 C1 1.347(2) . ?
O3 C11 1.445(2) . ?
N1 C1 1.279(2) . ?
N1 H1N 0.9176 . ?
N2 N3 1.3082(19) . ?
N2 C2 1.327(2) . ?
N3 C3 1.430(2) . ?
N4 C10 1.151(2) . ?
N5 C16 1.341(2) . ?
N5 C12 1.346(2) . ?
C1 C2 1.457(2) . ?
C2 C10 1.433(2) . ?
C3 C8 1.409(2) . ?
C3 C4 1.410(2) . ?
C4 C5 1.381(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.391(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.383(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.405(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.514(2) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 C13 1.381(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.381(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.384(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.383(2) . ?
C15 H15 0.9500 . ?
C16 H16 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
_geom_hbond_publ_flag
N1 H1N O2 0.92 2.06 2.9669(18) 168.5 2_566 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
N1 Cu1 O1 C9 -112.7(2) . . . . ?
N3 Cu1 O1 C9 -2.46(18) . . . . ?
N5 Cu1 O1 C9 172.04(18) . . . . ?
C2 N2 N3 C3 -171.11(15) . . . . ?
C2 N2 N3 Cu1 17.4(2) . . . . ?
Cu1 N1 C1 O3 178.39(12) . . . . ?
Cu1 N1 C1 C2 -3.4(2) . . . . ?
C11 O3 C1 N1 5.6(3) . . . . ?
C11 O3 C1 C2 -172.77(14) . . . . ?
N3 N2 C2 C10 -177.69(15) . . . . ?
N3 N2 C2 C1 7.5(3) . . . . ?
N1 C1 C2 N2 -15.6(3) . . . . ?
O3 C1 C2 N2 162.77(16) . . . . ?
N1 C1 C2 C10 169.76(16) . . . . ?
O3 C1 C2 C10 -11.8(2) . . . . ?
N2 N3 C3 C8 -167.82(15) . . . . ?
Cu1 N3 C3 C8 3.5(2) . . . . ?
N2 N3 C3 C4 15.1(2) . . . . ?
Cu1 N3 C3 C4 -173.58(12) . . . . ?
C8 C3 C4 C5 3.3(2) . . . . ?
N3 C3 C4 C5 -179.54(15) . . . . ?
C3 C4 C5 C6 0.3(3) . . . . ?
C4 C5 C6 C7 -2.5(3) . . . . ?
C5 C6 C7 C8 1.0(3) . . . . ?
C6 C7 C8 C3 2.7(3) . . . . ?
C6 C7 C8 C9 -173.76(16) . . . . ?
C4 C3 C8 C7 -4.7(2) . . . . ?
N3 C3 C8 C7 178.22(15) . . . . ?
C4 C3 C8 C9 171.30(16) . . . . ?
N3 C3 C8 C9 -5.8(3) . . . . ?
Cu1 O1 C9 O2 179.97(13) . . . . ?
Cu1 O1 C9 C8 1.1(3) . . . . ?
C7 C8 C9 O2 0.8(2) . . . . ?
C3 C8 C9 O2 -175.36(16) . . . . ?
C7 C8 C9 O1 179.71(16) . . . . ?
C3 C8 C9 O1 3.6(3) . . . . ?
C16 N5 C12 C13 -0.5(3) . . . . ?
Cu1 N5 C12 C13 172.28(14) . . . . ?
N5 C12 C13 C14 0.1(3) . . . . ?
C12 C13 C14 C15 0.3(3) . . . . ?
C13 C14 C15 C16 -0.4(3) . . . . ?
C12 N5 C16 C15 0.4(3) . . . . ?
Cu1 N5 C16 C15 -172.06(15) . . . . ?
C14 C15 C16 N5 0.0(3) . . . . ?
