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#$Date: 2022-07-04 11:24:35 +0300 (Mon, 04 Jul 2022) $
#$Revision: 276523 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/56/8105624.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_8105624
loop_
_publ_author_name
'Ling, Zhao'
'Xin, Wang'
'Liguo, Yang'
'Linna, Gao'
_publ_section_title
;
 Crystal structure of
 ((5,5′-dimethoxy-2,2′-(1,2-phenylenebis(nitrilomethylidyne)))diphenolato-κ4
 O,N,O′,N′)copper(II), C22H18N2CuO4
;
_journal_issue                   2
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              303
_journal_page_last               304
_journal_paper_doi               10.1515/ncrs-2018-0361
_journal_volume                  234
_journal_year                    2019
_chemical_formula_sum            'C22 H18 Cu N2 O4'
_chemical_formula_weight         437.92
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 92.129(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.7861(11)
_cell_length_b                   5.3211(4)
_cell_length_c                   21.6563(16)
_cell_measurement_reflns_used    9883
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      28.47
_cell_measurement_theta_min      3.15
_cell_volume                     1817.9(2)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0286
_diffrn_reflns_av_unetI/netI     0.0166
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            24774
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.017
_diffrn_reflns_theta_max         25.017
_diffrn_reflns_theta_min         3.766
_exptl_absorpt_coefficient_mu    1.235
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.600
_exptl_crystal_description       block
_exptl_crystal_F_000             900
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   0.906
_exptl_transmission_factor_min   0.862
_refine_diff_density_max         0.330
_refine_diff_density_min         -0.256
_refine_diff_density_rms         0.059
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.113
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     264
_refine_ls_number_reflns         3205
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.113
_refine_ls_R_factor_all          0.0297
_refine_ls_R_factor_gt           0.0254
_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)+(0.0391P)²+0.8628P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0718
_refine_ls_wR_factor_ref         0.0765
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2888
_reflns_number_total             3205
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_ncrs-2018-0361_suppl.cif
_cod_data_source_block           1
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               8105624
_shelx_shelxl_version_number     2014/7
_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.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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 0.55216(2) 0.70941(5) 0.66651(2) 0.03281(10) Uani 1 1 d . . . . .
N1 N 0.59322(10) 0.9898(3) 0.71656(7) 0.0324(4) Uani 1 1 d . . . . .
N2 N 0.46405(10) 0.6937(3) 0.72637(7) 0.0321(4) Uani 1 1 d . . . . .
O1 O 0.88902(10) 1.0285(3) 0.51769(7) 0.0503(4) Uani 1 1 d . . . . .
O2 O 0.64259(10) 0.7268(3) 0.61170(7) 0.0478(4) Uani 1 1 d . . . . .
O3 O 0.51050(9) 0.4293(3) 0.62042(6) 0.0395(3) Uani 1 1 d . . . . .
O4 O 0.32969(11) -0.2400(3) 0.55813(8) 0.0490(4) Uani 1 1 d . . . . .
C1 C 0.88868(18) 0.8170(5) 0.47759(12) 0.0603(7) Uani 1 1 d . . . . .
H1A H 0.8878 0.6655 0.5016 0.090 Uiso 1 1 calc R U . . .
H1B H 0.9387 0.8196 0.4537 0.090 Uiso 1 1 calc R U . . .
H1C H 0.8393 0.8231 0.4503 0.090 Uiso 1 1 calc R U . . .
C2 C 0.76391(13) 0.8677(4) 0.56504(10) 0.0393(5) Uani 1 1 d . . . . .
H2 H 0.7596 0.7358 0.5369 0.047 Uiso 1 1 calc R U . . .
C3 C 0.82867(13) 1.0382(4) 0.56081(9) 0.0382(5) Uani 1 1 d . . . . .
C4 C 0.83739(15) 1.2385(4) 0.60250(11) 0.0448(5) Uani 1 1 d . . . . .
H4 H 0.8811 1.3542 0.5991 0.054 Uiso 1 1 calc R U . . .
C5 C 0.78127(15) 1.2609(4) 0.64774(11) 0.0436(5) Uani 1 1 d . . . . .
H5 H 0.7873 1.3939 0.6754 0.052 Uiso 1 1 calc R U . . .
C6 C 0.71327(12) 1.0892(4) 0.65473(9) 0.0347(4) Uani 1 1 d . . . . .
C7 C 0.70367(12) 0.8893(4) 0.61146(9) 0.0353(4) Uani 1 1 d . . . . .
C8 C 0.65797(13) 1.1290(4) 0.70358(9) 0.0364(4) Uani 1 1 d . . . . .
H8 H 0.6688 1.2676 0.7288 0.044 Uiso 1 1 calc R U . . .
C9 C 0.54211(12) 1.0421(4) 0.76736(9) 0.0334(4) Uani 1 1 d . . . . .
C10 C 0.55541(14) 1.2327(4) 0.81004(10) 0.0398(5) Uani 1 1 d . . . . .
H10 H 0.6019 1.3386 0.8070 0.048 Uiso 1 1 calc R U . . .
C11 C 0.49993(15) 1.2664(4) 0.85712(11) 0.0450(5) Uani 1 1 d . . . . .
H11 H 0.5091 1.3956 0.8855 0.054 Uiso 1 1 calc R U . . .
C12 C 0.43101(15) 1.1096(5) 0.86228(10) 0.0472(5) Uani 1 1 d . . . . .
H12 H 0.3935 1.1343 0.8939 0.057 Uiso 1 1 calc R U . . .
C13 C 0.41753(14) 0.9165(4) 0.82080(10) 0.0429(5) Uani 1 1 d . . . . .
H13 H 0.3715 0.8097 0.8250 0.051 Uiso 1 1 calc R U . . .
C14 C 0.47201(12) 0.8793(4) 0.77270(9) 0.0338(4) Uani 1 1 d . . . . .
C15 C 0.40166(12) 0.5323(4) 0.72438(9) 0.0349(4) Uani 1 1 d . . . . .
H15 H 0.3624 0.5443 0.7552 0.042 Uiso 1 1 calc R U . . .
C16 C 0.38841(12) 0.3424(4) 0.68003(9) 0.0333(4) Uani 1 1 d . . . . .
C17 C 0.44322(12) 0.2969(4) 0.63026(9) 0.0337(4) Uani 1 1 d . . . . .
C18 C 0.42381(13) 0.0969(4) 0.58957(9) 0.0380(5) Uani 1 1 d . . . . .
H18 H 0.4600 0.0630 0.5577 0.046 Uiso 1 1 calc R U . . .
C19 C 0.35265(13) -0.0498(4) 0.59576(9) 0.0384(5) Uani 1 1 d . . . . .
C20 C 0.29804(13) -0.0041(5) 0.64504(10) 0.0435(5) Uani 1 1 d . . . . .
H20 H 0.2501 -0.1027 0.6496 0.052 Uiso 1 1 calc R U . . .
C21 C 0.31625(13) 0.1839(4) 0.68523(10) 0.0404(5) Uani 1 1 d . . . . .
H21 H 0.2803 0.2111 0.7176 0.048 Uiso 1 1 calc R U . . .
C24 C 0.38329(17) -0.2969(5) 0.50765(11) 0.0518(6) Uani 1 1 d . . . . .
H24A H 0.3870 -0.1525 0.4813 0.078 Uiso 1 1 calc R U . . .
H24B H 0.3598 -0.4354 0.4844 0.078 Uiso 1 1 calc R U . . .
H24C H 0.4389 -0.3406 0.5236 0.078 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
O2 Cu1 O3 87.89(6) . .
O2 Cu1 N2 176.86(7) . .
O3 Cu1 N2 94.28(6) . .
O2 Cu1 N1 93.94(6) . .
O3 Cu1 N1 177.76(6) . .
N2 Cu1 N1 83.84(7) . .
C8 N1 C9 122.08(17) . .
C8 N1 Cu1 124.42(14) . .
C9 N1 Cu1 113.37(13) . .
C15 N2 C14 122.08(17) . .
C15 N2 Cu1 124.42(14) . .
C14 N2 Cu1 113.48(13) . .
C3 O1 C1 117.58(17) . .
C7 O2 Cu1 127.89(14) . .
C17 O3 Cu1 127.53(13) . .
C19 O4 C24 117.84(17) . .
O1 C1 H1A 109.5 . .
O1 C1 H1B 109.5 . .
H1A C1 H1B 109.5 . .
O1 C1 H1C 109.5 . .
H1A C1 H1C 109.5 . .
H1B C1 H1C 109.5 . .
C3 C2 C7 121.1(2) . .
C3 C2 H2 119.5 . .
C7 C2 H2 119.5 . .
O1 C3 C2 124.3(2) . .
O1 C3 C4 114.67(18) . .
C2 C3 C4 121.0(2) . .
C5 C4 C3 118.9(2) . .
C5 C4 H4 120.5 . .
C3 C4 H4 120.5 . .
C4 C5 C6 122.6(2) . .
C4 C5 H5 118.7 . .
C6 C5 H5 118.7 . .
C8 C6 C7 123.50(18) . .
C8 C6 C5 118.27(19) . .
C7 C6 C5 118.22(19) . .
O2 C7 C2 117.97(19) . .
O2 C7 C6 123.91(18) . .
C2 C7 C6 118.11(18) . .
N1 C8 C6 126.08(19) . .
N1 C8 H8 117.0 . .
C6 C8 H8 117.0 . .
C10 C9 C14 119.63(19) . .
C10 C9 N1 125.92(19) . .
C14 C9 N1 114.45(17) . .
C11 C10 C9 120.3(2) . .
C11 C10 H10 119.9 . .
C9 C10 H10 119.9 . .
C12 C11 C10 120.3(2) . .
C12 C11 H11 119.8 . .
C10 C11 H11 119.8 . .
C13 C12 C11 120.2(2) . .
C13 C12 H12 119.9 . .
C11 C12 H12 119.9 . .
C12 C13 C14 120.7(2) . .
C12 C13 H13 119.6 . .
C14 C13 H13 119.6 . .
C13 C14 N2 126.28(19) . .
C13 C14 C9 118.86(19) . .
N2 C14 C9 114.85(17) . .
N2 C15 C16 126.05(18) . .
N2 C15 H15 117.0 . .
C16 C15 H15 117.0 . .
C15 C16 C21 118.09(18) . .
C15 C16 C17 124.00(18) . .
C21 C16 C17 117.90(19) . .
O3 C17 C18 117.86(18) . .
O3 C17 C16 123.66(19) . .
C18 C17 C16 118.48(18) . .
C19 C18 C17 121.75(19) . .
C19 C18 H18 119.1 . .
C17 C18 H18 119.1 . .
O4 C19 C18 124.8(2) . .
O4 C19 C20 115.41(18) . .
C18 C19 C20 119.8(2) . .
C21 C20 C19 119.46(19) . .
C21 C20 H20 120.3 . .
C19 C20 H20 120.3 . .
C20 C21 C16 122.6(2) . .
C20 C21 H21 118.7 . .
C16 C21 H21 118.7 . .
O4 C24 H24A 109.5 . .
O4 C24 H24B 109.5 . .
H24A C24 H24B 109.5 . .
O4 C24 H24C 109.5 . .
H24A C24 H24C 109.5 . .
H24B C24 H24C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cu1 O2 1.8924(15) .
Cu1 O3 1.8979(14) .
Cu1 N2 1.9381(17) .
Cu1 N1 1.9416(17) .
N1 C8 1.301(3) .
N1 C9 1.416(2) .
N2 C15 1.306(3) .
N2 C14 1.410(3) .
O1 C3 1.359(2) .
O1 C1 1.421(3) .
O2 C7 1.295(2) .
O3 C17 1.299(2) .
O4 C19 1.341(3) .
O4 C24 1.439(3) .
C1 H1A 0.9600 .
C1 H1B 0.9600 .
C1 H1C 0.9600 .
C2 C3 1.373(3) .
C2 C7 1.414(3) .
C2 H2 0.9300 .
C3 C4 1.400(3) .
C4 C5 1.350(3) .
C4 H4 0.9300 .
C5 C6 1.422(3) .
C5 H5 0.9300 .
C6 C8 1.412(3) .
C6 C7 1.422(3) .
C8 H8 0.9300 .
C9 C10 1.383(3) .
C9 C14 1.413(3) .
C10 C11 1.380(3) .
C10 H10 0.9300 .
C11 C12 1.379(4) .
C11 H11 0.9300 .
C12 C13 1.376(3) .
C12 H12 0.9300 .
C13 C14 1.389(3) .
C13 H13 0.9300 .
C15 C16 1.405(3) .
C15 H15 0.9300 .
C16 C21 1.425(3) .
C16 C17 1.428(3) .
C17 C18 1.408(3) .
C18 C19 1.379(3) .
C18 H18 0.9300 .
C19 C20 1.418(3) .
C20 C21 1.350(3) .
C20 H20 0.9300 .
C21 H21 0.9300 .
C24 H24A 0.9600 .
C24 H24B 0.9600 .
C24 H24C 0.9600 .
