#------------------------------------------------------------------------------
#$Date: 2025-08-19 14:52:15 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301804 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/16/2211663.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_2211663
loop_
_publ_author_name
'Guo-Bing Yan'
'Ming-Hua Yang'
'Yun-Fa Zheng'
_publ_section_title
{4,6-Dichloro-2-[(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)iminomethyl]phenolato-κ²N,O}copper(II)
_journal_coeditor_code           WN2089
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m3481
_journal_page_last               m3482
_journal_paper_doi               10.1107/S1600536806049233
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          '[Cu (C18 H14 Cl2 N3 O2)2]'
_chemical_formula_moiety         'C36 H28 Cl4 Cu N6 O4'
_chemical_formula_sum            'C36 H28 Cl4 Cu N6 O4'
_chemical_formula_weight         813.98
_chemical_name_systematic
;
{4,6-Dichloro-2-[(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-
yl)iminomethyl]phenolato-κ²N,O}copper(II)
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/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                 91.5700(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   23.4341(17)
_cell_length_b                   6.7434(5)
_cell_length_c                   22.6048(16)
_cell_measurement_reflns_used    5244
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      25.04
_cell_measurement_theta_min      2.12
_cell_volume                     3570.8(4)
_computing_cell_refinement       APEX2
_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_data_reduction        APEX2
_computing_molecular_graphics    APEX2
_computing_publication_material  APEX2
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      273(2)
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'Bruker APEX-II area-detector'
_diffrn_measurement_method       'φ and ω'
_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  0.0306
_diffrn_reflns_av_sigmaI/netI    0.0261
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            10369
_diffrn_reflns_theta_full        25.19
_diffrn_reflns_theta_max         25.19
_diffrn_reflns_theta_min         1.74
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.960
_exptl_absorpt_correction_T_max  0.8853
_exptl_absorpt_correction_T_min  0.7361
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.514
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1660
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.549
_refine_diff_density_min         -0.370
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     233
_refine_ls_number_reflns         3172
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.084
_refine_ls_R_factor_all          0.0422
_refine_ls_R_factor_gt           0.0349
_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)+(0.0692P)²+0.3862P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1008
_refine_ls_wR_factor_ref         0.1051
_reflns_number_gt                2660
_reflns_number_total             3172
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            wn2089.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2211663
_cod_database_fobs_code          2211663
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -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
Cu Cu1 0.0000 0.13084(6) 0.2500 0.03850(15) Uani d S 1
N N1 0.02757(7) 0.0803(3) 0.17038(7) 0.0385(4) Uani d . 1
N N2 -0.08406(8) -0.1200(3) 0.07475(8) 0.0430(5) Uani d . 1
N N3 -0.06744(7) 0.0499(3) 0.04327(7) 0.0420(4) Uani d . 1
O O1 0.07314(6) 0.1923(3) 0.28143(7) 0.0490(4) Uani d . 1
O O2 -0.00544(8) 0.3147(3) 0.06217(8) 0.0569(5) Uani d . 1
C C1 -0.01213(9) 0.0260(3) 0.12484(9) 0.0385(5) Uani d . 1
C C2 -0.04701(10) -0.1319(3) 0.12329(10) 0.0421(5) Uani d . 1
C C3 -0.02511(10) 0.1510(3) 0.07489(10) 0.0409(5) Uani d . 1
C C4 -0.04889(13) -0.3040(4) 0.16436(12) 0.0627(7) Uani d . 1
H H4A -0.0259 -0.2762 0.1992 0.094 Uiso calc R 1
H H4B -0.0344 -0.4196 0.1451 0.094 Uiso calc R 1
H H4C -0.0876 -0.3274 0.1753 0.094 Uiso calc R 1
C C5 -0.09640(11) -0.2978(4) 0.03901(11) 0.0548(6) Uani d . 1
H H5A -0.0628 -0.3364 0.0186 0.082 Uiso calc R 1
H H5B -0.1265 -0.2693 0.0107 0.082 Uiso calc R 1
H H5C -0.1080 -0.4038 0.0644 0.082 Uiso calc R 1
C C6 -0.10449(10) 0.1333(3) -0.00074(10) 0.0430(5) Uani d . 1
C C7 -0.16238(11) 0.0881(4) -0.00231(11) 0.0565(7) Uani d . 1
H H7 -0.1776 0.0069 0.0265 0.068 Uiso calc R 1
C C8 -0.19710(13) 0.1652(5) -0.04714(14) 0.0707(9) Uani d . 1
H H8 -0.2356 0.1320 -0.0493 0.085 Uiso calc R 1
C C9 -0.17462(15) 0.2918(5) -0.08884(14) 0.0766(9) Uani d . 1
H H9 -0.1979 0.3434 -0.1190 0.092 Uiso calc R 1
C C10 -0.11806(15) 0.3403(4) -0.08529(13) 0.0681(8) Uani d . 1
H H10 -0.1035 0.4295 -0.1124 0.082 Uiso calc R 1
C C11 -0.08193(12) 0.2600(4) -0.04240(10) 0.0535(6) Uani d . 1
H H11 -0.0432 0.2903 -0.0414 0.064 Uiso calc R 1
C C12 0.11991(9) 0.2175(3) 0.25324(9) 0.0393(5) Uani d . 1
C C13 0.17017(9) 0.2768(3) 0.28486(10) 0.0404(5) Uani d . 1
C C14 0.22127(9) 0.3076(3) 0.25816(11) 0.0452(6) Uani d . 1
H H14 0.2533 0.3473 0.2804 0.054 Uiso calc R 1
C C15 0.22463(9) 0.2788(3) 0.19751(11) 0.0443(5) Uani d . 1
C C16 0.17817(10) 0.2199(4) 0.16449(11) 0.0438(5) Uani d . 1
H H16 0.1813 0.2000 0.1240 0.053 Uiso calc R 1
C C17 0.12514(9) 0.1891(3) 0.19143(10) 0.0389(5) Uani d . 1
C C18 0.07861(10) 0.1245(3) 0.15395(10) 0.0407(5) Uani d . 1
H H18 0.0857 0.1131 0.1138 0.049 Uiso calc R 1
Cl Cl1 0.16534(3) 0.30613(10) 0.36073(3) 0.05329(19) Uani d . 1
Cl Cl2 0.28948(3) 0.31602(11) 0.16363(3) 0.0640(2) Uani d . 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'
Cl Cl 0.1484 0.1585 '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 O1 2 . 154.58(11) y
O1 Cu1 N1 2 . 90.65(7) y
O1 Cu1 N1 . . 93.73(7) y
O1 Cu1 N1 2 2 93.73(7) ?
O1 Cu1 N1 . 2 90.65(7) ?
N1 Cu1 N1 . 2 159.96(11) y
C18 N1 C1 . . 116.35(17) ?
C18 N1 Cu1 . . 123.59(15) ?
C1 N1 Cu1 . . 119.08(13) ?
C2 N2 N3 . . 105.76(17) ?
C2 N2 C5 . . 119.9(2) ?
N3 N2 C5 . . 116.01(18) ?
C3 N3 N2 . . 110.10(17) ?
C3 N3 C6 . . 125.6(2) ?
N2 N3 C6 . . 120.26(18) ?
C12 O1 Cu1 . . 128.14(13) ?
C2 C1 N1 . . 127.7(2) ?
C2 C1 C3 . . 109.25(19) ?
N1 C1 C3 . . 122.7(2) ?
C1 C2 N2 . . 110.07(19) ?
C1 C2 C4 . . 129.1(2) ?
N2 C2 C4 . . 120.8(2) ?
O2 C3 N3 . . 126.0(2) ?
O2 C3 C1 . . 129.5(2) ?
N3 C3 C1 . . 104.47(19) ?
C2 C4 H4A . . 109.5 ?
C2 C4 H4B . . 109.5 ?
H4A C4 H4B . . 109.5 ?
C2 C4 H4C . . 109.5 ?
H4A C4 H4C . . 109.5 ?
H4B C4 H4C . . 109.5 ?
N2 C5 H5A . . 109.5 ?
N2 C5 H5B . . 109.5 ?
H5A C5 H5B . . 109.5 ?
N2 C5 H5C . . 109.5 ?
H5A C5 H5C . . 109.5 ?
H5B C5 H5C . . 109.5 ?
C11 C6 C7 . . 120.5(2) ?
C11 C6 N3 . . 118.9(2) ?
C7 C6 N3 . . 120.6(2) ?
C8 C7 C6 . . 119.4(3) ?
C8 C7 H7 . . 120.3 ?
C6 C7 H7 . . 120.3 ?
C7 C8 C9 . . 120.2(3) ?
C7 C8 H8 . . 119.9 ?
C9 C8 H8 . . 119.9 ?
C10 C9 C8 . . 119.6(3) ?
C10 C9 H9 . . 120.2 ?
C8 C9 H9 . . 120.2 ?
C9 C10 C11 . . 121.5(3) ?
C9 C10 H10 . . 119.2 ?
C11 C10 H10 . . 119.2 ?
C10 C11 C6 . . 118.7(3) ?
C10 C11 H11 . . 120.6 ?
C6 C11 H11 . . 120.6 ?
O1 C12 C13 . . 119.5(2) ?
O1 C12 C17 . . 124.35(19) ?
C13 C12 C17 . . 116.2(2) ?
C14 C13 C12 . . 122.9(2) ?
C14 C13 Cl1 . . 119.99(17) ?
C12 C13 Cl1 . . 117.07(17) ?
C13 C14 C15 . . 119.2(2) ?
C13 C14 H14 . . 120.4 ?
C15 C14 H14 . . 120.4 ?
C16 C15 C14 . . 121.0(2) ?
C16 C15 Cl2 . . 119.72(19) ?
C14 C15 Cl2 . . 119.24(17) ?
C15 C16 C17 . . 120.4(2) ?
C15 C16 H16 . . 119.8 ?
C17 C16 H16 . . 119.8 ?
C16 C17 C12 . . 120.3(2) ?
C16 C17 C18 . . 117.0(2) ?
C12 C17 C18 . . 122.6(2) ?
N1 C18 C17 . . 126.5(2) ?
N1 C18 H18 . . 116.8 ?
C17 C18 H18 . . 116.8 ?
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 2 1.8835(15) ?
Cu1 O1 . 1.8835(15) y
Cu1 N1 . 1.9587(17) y
Cu1 N1 2 1.9587(17) ?
N1 C18 . 1.297(3) ?
N1 C1 . 1.417(3) ?
N2 C2 . 1.383(3) ?
N2 N3 . 1.409(3) ?
N2 C5 . 1.470(3) ?
N3 C3 . 1.386(3) ?
N3 C6 . 1.419(3) ?
O1 C12 . 1.294(2) ?
O2 C3 . 1.233(3) ?
C1 C2 . 1.342(3) ?
C1 C3 . 1.435(3) ?
C2 C4 . 1.488(3) ?
C4 H4A . 0.9600 ?
C4 H4B . 0.9600 ?
C4 H4C . 0.9600 ?
C5 H5A . 0.9600 ?
C5 H5B . 0.9600 ?
C5 H5C . 0.9600 ?
C6 C11 . 1.387(3) ?
C6 C7 . 1.390(3) ?
C7 C8 . 1.384(4) ?
C7 H7 . 0.9300 ?
C8 C9 . 1.386(5) ?
C8 H8 . 0.9300 ?
C9 C10 . 1.366(5) ?
C9 H9 . 0.9300 ?
C10 C11 . 1.380(4) ?
C10 H10 . 0.9300 ?
C11 H11 . 0.9300 ?
C12 C13 . 1.418(3) ?
C12 C17 . 1.419(3) ?
C13 C14 . 1.371(3) ?
C13 Cl1 . 1.733(2) ?
C14 C15 . 1.389(3) ?
C14 H14 . 0.9300 ?
C15 C16 . 1.362(3) ?
C15 Cl2 . 1.739(2) ?
C16 C17 . 1.414(3) ?
C16 H16 . 0.9300 ?
C17 C18 . 1.430(3) ?
C18 H18 . 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
C11 H11 O2 . 0.93 2.49 2.950(3) 111.0
C5 H5A O2 5 0.96 2.46 3.352(3) 153.8
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139041598
