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#$Date: 2025-08-19 00:06:14 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301780 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/15/1551555.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_1551555
loop_
_publ_author_name
'MITSUHASHI, Ryoji'
'MIYAZAKI, Yusuke'
'HOSOYA, Satoshi'
'MIKURIYA, Masahiro'
_publ_section_title
;
 Synthesis and Crystal Structure of
 Bis[2-(2-imidazolinyl)phenolato]copper(II)
;
_journal_issue                   0
_journal_name_full               'X-ray Structure Analysis Online'
_journal_page_first              11
_journal_paper_doi               10.2116/xraystruct.34.11
_journal_volume                  34
_journal_year                    2018
_chemical_formula_moiety         'C18 H18 Cu N4 O2'
_chemical_formula_sum            'C18 H18 Cu N4 O2'
_chemical_formula_weight         385.90
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 112.0280(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.2964(9)
_cell_length_b                   10.4722(10)
_cell_length_c                   8.8271(9)
_cell_measurement_reflns_used    1976
_cell_measurement_temperature    90(2)
_cell_measurement_theta_max      27.73
_cell_measurement_theta_min      2.36
_cell_volume                     796.62(14)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_publication_material  'Yadokari-XG 2009 (Wakita,Nemoto et al., 2009)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      90(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.964
_diffrn_measurement_device_type  'Bruker APEX CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0206
_diffrn_reflns_av_unetI/netI     0.0269
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.964
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            5025
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.964
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.431
_diffrn_reflns_theta_min         2.363
_exptl_absorpt_coefficient_mu    1.391
_exptl_absorpt_correction_T_max  0.897
_exptl_absorpt_correction_T_min  0.664
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.609
_exptl_crystal_description       platelet
_exptl_crystal_F_000             398
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.080
_refine_diff_density_max         0.561
_refine_diff_density_min         -0.253
_refine_diff_density_rms         0.082
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     119
_refine_ls_number_reflns         1943
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0386
_refine_ls_R_factor_gt           0.0306
_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)+(0.0504P)²+0.2003P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0803
_refine_ls_wR_factor_ref         0.0844
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1632
_reflns_number_total             1943
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            34_11_1.txt
_cod_data_source_block           1110171m_0ma
_cod_database_code               1551555
_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.
;
_shelx_estimated_absorpt_t_min   0.664
_shelx_estimated_absorpt_t_max   0.897
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
Cu1 Cu 0.5000 0.5000 0.5000 0.01375(12) Uani 1 2 d S . P
O1 O 0.36191(15) 0.53932(12) 0.27864(15) 0.0163(3) Uani 1 1 d . . .
C1 C 0.3142(2) 0.65392(16) 0.2186(2) 0.0144(4) Uani 1 1 d . . .
C2 C 0.1817(2) 0.66368(17) 0.0725(2) 0.0176(4) Uani 1 1 d . . .
H2 H 0.1306 0.5879 0.0204 0.021 Uiso 1 1 calc R U .
C3 C 0.1248(2) 0.78044(18) 0.0036(2) 0.0201(4) Uani 1 1 d . . .
H3 H 0.0363 0.7836 -0.0954 0.024 Uiso 1 1 calc R U .
C4 C 0.1953(2) 0.89379(17) 0.0773(2) 0.0191(4) Uani 1 1 d . . .
H4 H 0.1540 0.9741 0.0312 0.023 Uiso 1 1 calc R U .
C5 C 0.3266(2) 0.88715(17) 0.2189(2) 0.0167(4) Uani 1 1 d . . .
H5 H 0.3754 0.9640 0.2698 0.020 Uiso 1 1 calc R U .
C6 C 0.3895(2) 0.76948(16) 0.2892(2) 0.0141(4) Uani 1 1 d . . .
C7 C 0.5355(2) 0.76768(16) 0.4302(2) 0.0134(4) Uani 1 1 d . . .
N1 N 0.62358(18) 0.87554(15) 0.47881(18) 0.0156(3) Uani 1 1 d . . .
H1 H 0.619(3) 0.929(2) 0.411(3) 0.020(6) Uiso 1 1 d . . .
C8 C 0.7770(2) 0.83688(17) 0.5933(2) 0.0164(4) Uani 1 1 d . . .
H8 H 0.8189 0.8982 0.6848 0.020 Uiso 1 1 calc R U .
H8A H 0.8515 0.8277 0.5380 0.020 Uiso 1 1 calc R U .
C9 C 0.7403(2) 0.70793(17) 0.6518(2) 0.0181(4) Uani 1 1 d . . .
H9 H 0.8246 0.6458 0.6661 0.022 Uiso 1 1 calc R U .
H9A H 0.7256 0.7171 0.7567 0.022 Uiso 1 1 calc R U .
N2 N 0.59520(18) 0.66715(14) 0.52048(17) 0.0151(3) Uani 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'
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
O1 Cu1 O1 180.00(5) . 3_666
O1 Cu1 N2 89.50(6) . 3_666
O1 Cu1 N2 90.50(6) 3_666 3_666
O1 Cu1 N2 90.50(6) . .
O1 Cu1 N2 89.50(6) 3_666 .
N2 Cu1 N2 180.0 3_666 .
C1 O1 Cu1 126.43(11) . .
O1 C1 C2 118.59(15) . .
O1 C1 C6 124.26(16) . .
C2 C1 C6 117.13(16) . .
C3 C2 C1 121.66(17) . .
C3 C2 H2 119.2 . .
C1 C2 H2 119.2 . .
C2 C3 C4 120.91(17) . .
C2 C3 H3 119.5 . .
C4 C3 H3 119.5 . .
C5 C4 C3 118.71(17) . .
C5 C4 H4 120.6 . .
C3 C4 H4 120.6 . .
C4 C5 C6 121.56(17) . .
C4 C5 H5 119.2 . .
C6 C5 H5 119.2 . .
C5 C6 C1 119.93(16) . .
C5 C6 C7 119.25(16) . .
C1 C6 C7 120.77(15) . .
N2 C7 N1 113.90(15) . .
N2 C7 C6 125.16(16) . .
N1 C7 C6 120.93(15) . .
C7 N1 C8 107.63(14) . .
C7 N1 H1 118.8(16) . .
C8 N1 H1 118.1(16) . .
N1 C8 C9 101.19(14) . .
N1 C8 H8 111.5 . .
C9 C8 H8 111.5 . .
N1 C8 H8A 111.5 . .
C9 C8 H8A 111.5 . .
H8 C8 H8A 109.3 . .
N2 C9 C8 104.19(13) . .
N2 C9 H9 110.9 . .
C8 C9 H9 110.9 . .
N2 C9 H9A 110.9 . .
C8 C9 H9A 110.9 . .
H9 C9 H9A 108.9 . .
C7 N2 C9 107.42(14) . .
C7 N2 Cu1 126.41(12) . .
C9 N2 Cu1 125.87(11) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cu1 O1 1.9375(12) .
Cu1 O1 1.9375(12) 3_666
Cu1 N2 1.9390(15) 3_666
Cu1 N2 1.9390(15) .
O1 C1 1.320(2) .
C1 C2 1.414(2) .
C1 C6 1.420(2) .
C2 C3 1.380(3) .
C2 H2 0.9500 .
C3 C4 1.394(3) .
C3 H3 0.9500 .
C4 C5 1.383(2) .
C4 H4 0.9500 .
C5 C6 1.405(2) .
C5 H5 0.9500 .
C6 C7 1.457(2) .
C7 N2 1.312(2) .
C7 N1 1.367(2) .
N1 C8 1.462(2) .
N1 H1 0.81(2) .
C8 C9 1.529(2) .
C8 H8 0.9900 .
C8 H8A 0.9900 .
C9 N2 1.474(2) .
C9 H9 0.9900 .
C9 H9A 0.9900 .
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
N1 H1 O1 0.81(2) 2.10(2) 2.890(2) 167(2) 2_655
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
Cu1 O1 C1 C2 -162.06(13)
Cu1 O1 C1 C6 19.5(3)
O1 C1 C2 C3 179.53(18)
C6 C1 C2 C3 -2.0(3)
C1 C2 C3 C4 -0.8(3)
C2 C3 C4 C5 1.8(3)
C3 C4 C5 C6 0.0(3)
C4 C5 C6 C1 -2.7(3)
C4 C5 C6 C7 174.69(17)
O1 C1 C6 C5 -177.92(18)
C2 C1 C6 C5 3.7(3)
O1 C1 C6 C7 4.7(3)
C2 C1 C6 C7 -173.75(17)
C5 C6 C7 N2 170.00(18)
C1 C6 C7 N2 -12.6(3)
C5 C6 C7 N1 -10.3(3)
C1 C6 C7 N1 167.08(17)
N2 C7 N1 C8 13.9(2)
C6 C7 N1 C8 -165.81(16)
C7 N1 C8 C9 -22.12(18)
N1 C8 C9 N2 22.53(18)
N1 C7 N2 C9 1.8(2)
C6 C7 N2 C9 -178.48(17)
N1 C7 N2 Cu1 175.80(12)
C6 C7 N2 Cu1 -4.5(3)
C8 C9 N2 C7 -15.86(19)
C8 C9 N2 Cu1 170.14(12)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168302937
