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#$Date: 2025-08-19 16:18:28 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301805 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/66/2226689.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2226689
loop_
_publ_author_name
'Hatefi, Mehdi'
'Sheikhshoaie, Iran'
'Moghadam, Majid'
'Mirkhani, Valiollah'
'Kia, Reza'
_publ_section_title
;
 Bis[μ-(E)-N'-(4-oxido-4-phenylbut-3-en-2-ylidene)benzohydrazidato]bis[pyridinecopper(II)]
;
_journal_coeditor_code           SU2179
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m726
_journal_page_last               m727
_journal_paper_doi               10.1107/S1600536810019902
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          '[Cu2 (C17 H14 N2 O2)2 (C5 H5 N)2]'
_chemical_formula_moiety         'C44 H38 Cu2 N6 O4'
_chemical_formula_sum            'C44 H38 Cu2 N6 O4'
_chemical_formula_weight         841.88
_chemical_name_systematic
Bis[μ-(E)-N'-(4-oxido-4-phenylbut-3-en-2-ylidene)benzohydrazidato]bis[pyridinecopper(II)]
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 122.65(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   9.2678(19)
_cell_length_b                   20.903(4)
_cell_length_c                   11.907(4)
_cell_measurement_reflns_used    2500
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.78
_cell_measurement_theta_min      2.25
_cell_volume                     1942.2(10)
_computing_cell_refinement       'X-AREA (Stoe & Cie, 2007)'
_computing_data_collection       'X-AREA (Stoe & Cie, 2007)'
_computing_data_reduction        'X-RED (Stoe & Cie, 2007)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material
'SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Stoe IPDS II'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0855
_diffrn_reflns_av_sigmaI/netI    0.0616
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            22473
_diffrn_reflns_theta_full        24.99
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         1.95
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.147
_exptl_absorpt_correction_T_max  1.17928
_exptl_absorpt_correction_T_min  0.79106
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'(MULABS in PLATON; Blessing, 1995; Spek, 2009)'
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.440
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             868
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.602
_refine_diff_density_min         -0.240
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.983
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     248
_refine_ls_number_reflns         3419
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.983
_refine_ls_R_factor_all          0.0850
_refine_ls_R_factor_gt           0.0478
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0421P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0817
_refine_ls_wR_factor_ref         0.0911
_reflns_number_gt                2396
_reflns_number_total             3419
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            su2179.cif
_cod_data_source_block           I
_cod_original_cell_volume        1942.2(8)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2226689
_cod_database_fobs_code          2226689
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu Cu1 0.72076(6) 0.989490(19) 0.59789(4) 0.03829(14) Uani d . 1 . .
O O1 0.8469(3) 0.91348(12) 0.6768(2) 0.0487(6) Uani d . 1 . .
O O2 0.5995(3) 1.06734(11) 0.5062(2) 0.0483(7) Uani d . 1 . .
N N1 0.7488(4) 0.98572(15) 0.4481(3) 0.0472(5) Uani d . 1 . .
N N2 0.6903(4) 1.04093(15) 0.3654(3) 0.0472(5) Uani d . 1 . .
N N3 0.7158(4) 1.01066(15) 0.7612(3) 0.0414(7) Uani d . 1 . .
C C1 1.0439(5) 0.8085(2) 0.8269(4) 0.0516(10) Uani d . 1 . .
H H1A 1.0469 0.8445 0.8738 0.062 Uiso calc R 1 . .
C C2 1.1150(5) 0.7523(2) 0.8941(4) 0.0604(12) Uani d . 1 . .
H H2A 1.1679 0.7510 0.9862 0.073 Uiso calc R 1 . .
C C3 1.1088(6) 0.6981(2) 0.8270(5) 0.0641(12) Uani d . 1 . .
H H3A 1.1566 0.6601 0.8730 0.077 Uiso calc R 1 . .
C C4 1.0307(6) 0.7005(2) 0.6901(5) 0.0635(12) Uani d . 1 . .
H H4A 1.0251 0.6637 0.6438 0.076 Uiso calc R 1 . .
C C5 0.9611(5) 0.75679(18) 0.6218(4) 0.0517(10) Uani d . 1 . .
H H5A 0.9094 0.7580 0.5297 0.062 Uiso calc R 1 . .
C C6 0.9678(4) 0.81204(17) 0.6902(4) 0.0404(9) Uani d . 1 . .
C C7 0.8931(5) 0.87399(17) 0.6172(4) 0.0435(9) Uani d . 1 . .
C C8 0.8818(5) 0.88587(18) 0.5004(4) 0.0486(10) Uani d . 1 . .
H H8A 0.9209 0.8535 0.4696 0.058 Uiso calc R 1 . .
C C9 0.8162(5) 0.94287(19) 0.4177(4) 0.0509(10) Uani d . 1 . .
C C10 0.8303(6) 0.9466(2) 0.2981(4) 0.0630(12) Uani d . 1 . .
H H10A 0.8992 0.9829 0.3068 0.095 Uiso calc R 1 . .
H H10B 0.7180 0.9512 0.2190 0.095 Uiso calc R 1 . .
H H10C 0.8826 0.9082 0.2921 0.095 Uiso calc R 1 . .
C C11 0.6189(4) 1.07952(16) 0.4061(3) 0.0377(8) Uani d . 1 . .
C C12 0.5563(4) 1.14232(16) 0.3377(3) 0.0390(8) Uani d . 1 . .
C C13 0.5943(5) 1.16228(19) 0.2453(4) 0.0555(11) Uani d . 1 . .
H H13A 0.6581 1.1360 0.2249 0.067 Uiso calc R 1 . .
C C14 0.5383(6) 1.2207(2) 0.1837(5) 0.0695(13) Uani d . 1 . .
H H14A 0.5662 1.2338 0.1231 0.083 Uiso calc R 1 . .
C C15 0.4425(6) 1.2595(2) 0.2104(5) 0.0663(13) Uani d . 1 . .
H H15A 0.4033 1.2985 0.1669 0.080 Uiso calc R 1 . .
C C16 0.4035(5) 1.2407(2) 0.3021(5) 0.0625(12) Uani d . 1 . .
H H16A 0.3388 1.2673 0.3211 0.075 Uiso calc R 1 . .
C C17 0.4606(5) 1.18260(17) 0.3654(4) 0.0476(10) Uani d . 1 . .
H H17A 0.4347 1.1702 0.4276 0.057 Uiso calc R 1 . .
C C18 0.7643(6) 0.96766(19) 0.8587(4) 0.0561(11) Uani d . 1 . .
H H18A 0.7996 0.9274 0.8495 0.067 Uiso calc R 1 . .
C C19 0.7642(7) 0.9806(3) 0.9721(4) 0.0797(15) Uani d . 1 . .
H H19A 0.8004 0.9498 1.0385 0.096 Uiso calc R 1 . .
C C20 0.7102(7) 1.0389(2) 0.9855(5) 0.0814(16) Uani d . 1 . .
H H20A 0.7094 1.0486 1.0614 0.098 Uiso calc R 1 . .
C C21 0.6573(6) 1.0830(2) 0.8863(4) 0.0700(13) Uani d . 1 . .
H H21A 0.6188 1.1230 0.8931 0.084 Uiso calc R 1 . .
C C22 0.6618(5) 1.06729(19) 0.7760(4) 0.0514(10) Uani d . 1 . .
H H22A 0.6256 1.0976 0.7087 0.062 Uiso calc R 1 . .
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O1 Cu1 N1 . . 93.94(12) ?
O1 Cu1 O2 . . 174.68(10) ?
N1 Cu1 O2 . . 80.87(12) ?
O1 Cu1 N3 . . 92.01(12) ?
N1 Cu1 N3 . . 168.38(13) ?
O2 Cu1 N3 . . 92.90(11) ?
C7 O1 Cu1 . . 123.9(2) ?
C11 O2 Cu1 . . 110.4(2) ?
C9 N1 N2 . . 116.4(3) ?
C9 N1 Cu1 . . 129.1(3) ?
N2 N1 Cu1 . . 114.5(2) ?
C11 N2 N1 . . 109.2(3) ?
C22 N3 C18 . . 117.1(3) ?
C22 N3 Cu1 . . 121.8(2) ?
C18 N3 Cu1 . . 121.1(3) ?
C2 C1 C6 . . 120.8(4) ?
C2 C1 H1A . . 119.6 ?
C6 C1 H1A . . 119.6 ?
C3 C2 C1 . . 120.8(4) ?
C3 C2 H2A . . 119.6 ?
C1 C2 H2A . . 119.6 ?
C2 C3 C4 . . 119.3(4) ?
C2 C3 H3A . . 120.4 ?
C4 C3 H3A . . 120.4 ?
C5 C4 C3 . . 120.5(4) ?
C5 C4 H4A . . 119.7 ?
C3 C4 H4A . . 119.7 ?
C4 C5 C6 . . 120.2(4) ?
C4 C5 H5A . . 119.9 ?
C6 C5 H5A . . 119.9 ?
C1 C6 C5 . . 118.4(3) ?
C1 C6 C7 . . 120.6(3) ?
C5 C6 C7 . . 120.9(3) ?
O1 C7 C8 . . 125.1(3) ?
O1 C7 C6 . . 114.6(3) ?
C8 C7 C6 . . 120.3(3) ?
C7 C8 C9 . . 128.0(3) ?
C7 C8 H8A . . 116.0 ?
C9 C8 H8A . . 116.0 ?
N1 C9 C8 . . 118.9(3) ?
N1 C9 C10 . . 123.3(4) ?
C8 C9 C10 . . 117.8(3) ?
C9 C10 H10A . . 109.5 ?
C9 C10 H10B . . 109.5 ?
H10A C10 H10B . . 109.5 ?
C9 C10 H10C . . 109.5 ?
H10A C10 H10C . . 109.5 ?
H10B C10 H10C . . 109.5 ?
N2 C11 O2 . . 124.3(3) ?
N2 C11 C12 . . 118.2(3) ?
O2 C11 C12 . . 117.4(3) ?
C17 C12 C13 . . 118.3(3) ?
C17 C12 C11 . . 121.1(3) ?
C13 C12 C11 . . 120.6(3) ?
C14 C13 C12 . . 120.4(4) ?
C14 C13 H13A . . 119.8 ?
C12 C13 H13A . . 119.8 ?
C15 C14 C13 . . 120.8(4) ?
C15 C14 H14A . . 119.6 ?
C13 C14 H14A . . 119.6 ?
C14 C15 C16 . . 119.9(4) ?
C14 C15 H15A . . 120.1 ?
C16 C15 H15A . . 120.1 ?
C17 C16 C15 . . 119.8(4) ?
C17 C16 H16A . . 120.1 ?
C15 C16 H16A . . 120.1 ?
C16 C17 C12 . . 120.9(4) ?
C16 C17 H17A . . 119.6 ?
C12 C17 H17A . . 119.6 ?
N3 C18 C19 . . 122.7(4) ?
N3 C18 H18A . . 118.6 ?
C19 C18 H18A . . 118.6 ?
C20 C19 C18 . . 119.1(4) ?
C20 C19 H19A . . 120.4 ?
C18 C19 H19A . . 120.4 ?
C19 C20 C21 . . 119.1(4) ?
C19 C20 H20A . . 120.4 ?
C21 C20 H20A . . 120.4 ?
C20 C21 C22 . . 118.9(4) ?
C20 C21 H21A . . 120.5 ?
C22 C21 H21A . . 120.5 ?
N3 C22 C21 . . 123.0(4) ?
N3 C22 H22A . . 118.5 ?
C21 C22 H22A . . 118.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Cu1 O1 . 1.894(2) ?
Cu1 N1 . 1.938(3) ?
Cu1 O2 . 1.944(2) ?
Cu1 N3 . 2.018(3) ?
O1 C7 . 1.301(4) ?
O2 C11 . 1.323(4) ?
N1 C9 . 1.252(5) ?
N1 N2 . 1.421(4) ?
N2 C11 . 1.292(4) ?
N3 C22 . 1.333(5) ?
N3 C18 . 1.340(4) ?
C1 C2 . 1.372(5) ?
C1 C6 . 1.383(5) ?
C1 H1A . 0.9300 ?
C2 C3 . 1.370(6) ?
C2 H2A . 0.9300 ?
C3 C4 . 1.381(6) ?
C3 H3A . 0.9300 ?
C4 C5 . 1.378(5) ?
C4 H4A . 0.9300 ?
C5 C6 . 1.395(5) ?
C5 H5A . 0.9300 ?
C6 C7 . 1.504(5) ?
C7 C8 . 1.361(5) ?
C8 C9 . 1.453(5) ?
C8 H8A . 0.9300 ?
C9 C10 . 1.500(5) ?
C10 H10A . 0.9600 ?
C10 H10B . 0.9600 ?
C10 H10C . 0.9600 ?
C11 C12 . 1.488(5) ?
C12 C17 . 1.385(5) ?
C12 C13 . 1.389(5) ?
C13 C14 . 1.373(6) ?
C13 H13A . 0.9300 ?
C14 C15 . 1.361(6) ?
C14 H14A . 0.9300 ?
C15 C16 . 1.379(6) ?
C15 H15A . 0.9300 ?
C16 C17 . 1.376(5) ?
C16 H16A . 0.9300 ?
C17 H17A . 0.9300 ?
C18 C19 . 1.377(6) ?
C18 H18A . 0.9300 ?
C19 C20 . 1.359(6) ?
C19 H19A . 0.9300 ?
C20 C21 . 1.365(6) ?
C20 H20A . 0.9300 ?
C21 C22 . 1.376(5) ?
C21 H21A . 0.9300 ?
C22 H22A . 0.9300 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
C18 H18A O1 . 0.93 2.34 2.892(6) 117 y
C22 H22A O2 . 0.93 2.37 2.940(5) 119 y
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
N1 Cu1 O1 C7 . . . . -11.1(3) ?
N3 Cu1 O1 C7 . . . . 178.8(3) ?
N1 Cu1 O2 C11 . . . . -7.6(2) ?
N3 Cu1 O2 C11 . . . . 162.6(2) ?
O1 Cu1 N1 C9 . . . . 5.3(4) ?
O2 Cu1 N1 C9 . . . . -175.9(4) ?
N3 Cu1 N1 C9 . . . . 125.9(6) ?
O1 Cu1 N1 N2 . . . . -171.9(2) ?
O2 Cu1 N1 N2 . . . . 6.9(2) ?
N3 Cu1 N1 N2 . . . . -51.3(7) ?
C9 N1 N2 C11 . . . . 177.7(3) ?
Cu1 N1 N2 C11 . . . . -4.7(4) ?
O1 Cu1 N3 C22 . . . . 169.8(3) ?
N1 Cu1 N3 C22 . . . . 49.0(8) ?
O2 Cu1 N3 C22 . . . . -8.2(3) ?
O1 Cu1 N3 C18 . . . . -11.3(3) ?
N1 Cu1 N3 C18 . . . . -132.1(6) ?
O2 Cu1 N3 C18 . . . . 170.7(3) ?
C6 C1 C2 C3 . . . . -1.5(6) ?
C1 C2 C3 C4 . . . . 0.4(7) ?
C2 C3 C4 C5 . . . . 0.6(7) ?
C3 C4 C5 C6 . . . . -0.4(6) ?
C2 C1 C6 C5 . . . . 1.7(6) ?
C2 C1 C6 C7 . . . . -178.8(4) ?
C4 C5 C6 C1 . . . . -0.7(6) ?
C4 C5 C6 C7 . . . . 179.8(4) ?
Cu1 O1 C7 C8 . . . . 10.8(5) ?
Cu1 O1 C7 C6 . . . . -170.9(2) ?
C1 C6 C7 O1 . . . . -24.9(5) ?
C5 C6 C7 O1 . . . . 154.6(3) ?
C1 C6 C7 C8 . . . . 153.5(4) ?
C5 C6 C7 C8 . . . . -27.0(5) ?
O1 C7 C8 C9 . . . . -0.8(7) ?
C6 C7 C8 C9 . . . . -179.0(4) ?
N2 N1 C9 C8 . . . . 178.7(3) ?
Cu1 N1 C9 C8 . . . . 1.6(6) ?
N2 N1 C9 C10 . . . . -2.4(6) ?
Cu1 N1 C9 C10 . . . . -179.5(3) ?
C7 C8 C9 N1 . . . . -5.9(7) ?
C7 C8 C9 C10 . . . . 175.2(4) ?
N1 N2 C11 O2 . . . . -2.3(5) ?
N1 N2 C11 C12 . . . . 176.8(3) ?
Cu1 O2 C11 N2 . . . . 8.0(4) ?
Cu1 O2 C11 C12 . . . . -171.2(2) ?
N2 C11 C12 C17 . . . . 172.2(3) ?
O2 C11 C12 C17 . . . . -8.7(5) ?
N2 C11 C12 C13 . . . . -8.5(5) ?
O2 C11 C12 C13 . . . . 170.6(3) ?
C17 C12 C13 C14 . . . . 0.2(6) ?
C11 C12 C13 C14 . . . . -179.1(4) ?
C12 C13 C14 C15 . . . . -1.1(7) ?
C13 C14 C15 C16 . . . . 1.2(7) ?
C14 C15 C16 C17 . . . . -0.5(7) ?
C15 C16 C17 C12 . . . . -0.4(6) ?
C13 C12 C17 C16 . . . . 0.5(6) ?
C11 C12 C17 C16 . . . . 179.8(3) ?
C22 N3 C18 C19 . . . . -1.7(6) ?
Cu1 N3 C18 C19 . . . . 179.4(4) ?
N3 C18 C19 C20 . . . . 1.0(8) ?
C18 C19 C20 C21 . . . . 0.2(8) ?
C19 C20 C21 C22 . . . . -0.7(8) ?
C18 N3 C22 C21 . . . . 1.1(6) ?
Cu1 N3 C22 C21 . . . . -179.9(3) ?
C20 C21 C22 N3 . . . . 0.0(7) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139079196
