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#$Date: 2022-05-19 12:30:18 +0300 (Thu, 19 May 2022) $
#$Revision: 275552 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/53/8105311.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_8105311
loop_
_publ_author_name
'Jiang, Fang'
'Lei, Yan'
'Ting, Liu'
'Yang, Xiongzi'
'Wu, Qiong'
_publ_section_title
;
 Crystal structure of
 6,6′-((cyclohexane-1,2-diylbis(azanylylidene))bis(methanylylidene))bis(2-bromo-4-chlorophenolato-κ4
 N,N′,O,O′)nickel(II), C20H16Br2Cl2NiN2O2
;
_journal_issue                   4
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              863
_journal_page_last               864
_journal_paper_doi               10.1515/ncrs-2020-0061
_journal_volume                  235
_journal_year                    2020
_chemical_formula_sum            'C20 H16 Br2 Cl2 N2 Ni O2'
_chemical_formula_weight         605.78
_chemical_name_systematic
;
(2,2'-(cyclohexane-1,2-diylbis((nitrilo)methylylidene))bis(3-bromo-5-\
chlorophenolato))-nickel(II)
;
_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'
_atom_sites_solution_hydrogens   geom
_cell_angle_alpha                90
_cell_angle_beta                 115.14
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.6946(7)
_cell_length_b                   11.9262(7)
_cell_length_c                   14.9398(9)
_cell_measurement_reflns_used    3617
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      26.2719
_cell_measurement_theta_min      3.0125
_cell_volume                     2047.6(2)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      273(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Bruker APEX-III CCD'
_diffrn_measurement_method       'ω,and/f 0.5 deg'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0366
_diffrn_reflns_av_unetI/netI     0.0550
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            9563
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.392
_diffrn_reflns_theta_min         3.012
_exptl_absorpt_coefficient_mu    5.132
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.965
_exptl_crystal_description       block
_exptl_crystal_F_000             1192
_refine_diff_density_max         1.922
_refine_diff_density_min         -1.220
_refine_diff_density_rms         0.118
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         4135
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0627
_refine_ls_R_factor_gt           0.0386
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0259P)²+3.9104P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0757
_refine_ls_wR_factor_ref         0.0834
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3137
_reflns_number_total             4135
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_ncrs-2020-0061_suppl.cif
_cod_data_source_block           J30
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               8105311
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
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.41428(4) 0.63749(4) 0.10110(3) 0.02423(12) Uani 1 1 d . . . . .
Br2 Br 0.17101(4) 0.95819(4) 0.13096(4) 0.03514(15) Uani 1 1 d . . . . .
C1 C 0.5922(3) 0.7900(3) 0.1116(3) 0.0178(9) Uani 1 1 d . . . . .
C2 C 0.5621(3) 0.6755(3) 0.1065(3) 0.0182(9) Uani 1 1 d . . . . .
C3 C 0.6324(4) 0.5907(4) 0.1027(3) 0.0214(10) Uani 1 1 d . . . . .
H3 H 0.6087 0.5164 0.0996 0.026 Uiso 1 1 calc R U . . .
C4 C 0.7396(4) 0.6164(4) 0.1035(3) 0.0213(10) Uani 1 1 d . . . . .
C5 C 0.7732(4) 0.7256(4) 0.1064(3) 0.0222(10) Uani 1 1 d . . . . .
H5 H 0.8444 0.7422 0.1057 0.027 Uiso 1 1 calc R U . . .
C6 C 0.7010(4) 0.8135(4) 0.1105(3) 0.0186(9) Uani 1 1 d . . . . .
C7 C 0.7367(4) 0.9271(4) 0.1058(3) 0.0196(9) Uani 1 1 d . . . . .
H7 H 0.8054 0.9376 0.0988 0.023 Uiso 1 1 calc R U . . .
C8 C 0.7183(4) 1.1297(3) 0.0941(3) 0.0220(10) Uani 1 1 d . . . . .
H8 H 0.6703 1.1518 0.0255 0.026 Uiso 1 1 calc R U . . .
C9 C 0.8462(4) 1.1435(4) 0.1145(3) 0.0263(10) Uani 1 1 d . . . . .
H9A H 0.8652 1.0888 0.0756 0.032 Uiso 1 1 calc R U . . .
H9B H 0.8571 1.2175 0.0928 0.032 Uiso 1 1 calc R U . . .
C10 C 0.9293(4) 1.1294(4) 0.2220(3) 0.0264(10) Uani 1 1 d . . . . .
H10A H 1.0078 1.1462 0.2307 0.032 Uiso 1 1 calc R U . . .
H10B H 0.9276 1.0522 0.2417 0.032 Uiso 1 1 calc R U . . .
C11 C 0.8964(4) 1.2071(4) 0.2873(4) 0.0309(11) Uani 1 1 d . . . . .
H11A H 0.9067 1.2845 0.2727 0.037 Uiso 1 1 calc R U . . .
H11B H 0.9474 1.1931 0.3562 0.037 Uiso 1 1 calc R U . . .
C12 C 0.7696(4) 1.1884(4) 0.2700(3) 0.0264(10) Uani 1 1 d . . . . .
H12A H 0.7608 1.1129 0.2900 0.032 Uiso 1 1 calc R U . . .
H12B H 0.7497 1.2406 0.3102 0.032 Uiso 1 1 calc R U . . .
C13 C 0.6878(4) 1.2051(4) 0.1620(3) 0.0231(10) Uani 1 1 d . . . . .
H13 H 0.6891 1.2838 0.1436 0.028 Uiso 1 1 calc R U . . .
C14 C 0.4993(4) 1.2480(4) 0.1513(3) 0.0214(9) Uani 1 1 d . . . . .
H14 H 0.5261 1.3216 0.1629 0.026 Uiso 1 1 calc R U . . .
C15 C 0.3831(3) 1.2267(3) 0.1413(3) 0.0166(9) Uani 1 1 d . . . . .
C16 C 0.3124(4) 1.3196(3) 0.1369(3) 0.0197(9) Uani 1 1 d . . . . .
H16 H 0.3413 1.3922 0.1427 0.024 Uiso 1 1 calc R U . . .
C17 C 0.1995(4) 1.3008(3) 0.1237(3) 0.0216(10) Uani 1 1 d . . . . .
C18 C 0.1571(4) 1.1929(4) 0.1192(3) 0.0228(10) Uani 1 1 d . . . . .
H18 H 0.0811 1.1814 0.1111 0.027 Uiso 1 1 calc R U . . .
C19 C 0.2277(4) 1.1034(3) 0.1268(3) 0.0216(10) Uani 1 1 d . . . . .
C20 C 0.3428(4) 1.1140(3) 0.1352(3) 0.0174(9) Uani 1 1 d . . . . .
Cl1 Cl 0.82807(10) 0.50800(10) 0.09645(9) 0.0324(3) Uani 1 1 d . . . . .
Cl2 Cl 0.10612(10) 1.41293(10) 0.11323(10) 0.0368(3) Uani 1 1 d . . . . .
N1 N 0.6809(3) 1.0156(3) 0.1106(2) 0.0187(8) Uani 1 1 d . . . . .
N2 N 0.5686(3) 1.1730(3) 0.1453(3) 0.0189(8) Uani 1 1 d . . . . .
Ni1 Ni 0.54326(4) 1.01994(4) 0.12688(4) 0.01671(14) Uani 1 1 d . . . . .
O1 O 0.5200(2) 0.8663(2) 0.1153(2) 0.0175(6) Uani 1 1 d . . . . .
O2 O 0.4034(2) 1.0254(2) 0.1377(2) 0.0205(6) 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'
Br Br -0.2901 2.4595 '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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ni Ni 0.3393 1.1124 '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'
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 Ni1 O1 85.54(12) . .
O2 Ni1 N2 93.70(13) . .
O1 Ni1 N2 177.06(14) . .
O2 Ni1 N1 177.71(14) . .
O1 Ni1 N1 94.69(14) . .
N2 Ni1 N1 86.19(15) . .
C1 O1 Ni1 127.2(3) . .
C20 O2 Ni1 127.2(3) . .
N1 C7 C6 125.2(4) . .
N1 C7 H7 117.4 . .
C6 C7 H7 117.4 . .
N2 C14 C15 124.8(4) . .
N2 C14 H14 117.6 . .
C15 C14 H14 117.6 . .
C4 C5 C6 120.7(4) . .
C4 C5 H5 119.7 . .
C6 C5 H5 119.7 . .
C17 C16 C15 118.8(4) . .
C17 C16 H16 120.6 . .
C15 C16 H16 120.6 . .
O1 C1 C2 119.8(4) . .
O1 C1 C6 124.5(4) . .
C2 C1 C6 115.7(4) . .
C7 N1 C8 121.0(4) . .
C7 N1 Ni1 126.6(3) . .
C8 N1 Ni1 112.2(3) . .
C5 C6 C1 120.5(4) . .
C5 C6 C7 118.3(4) . .
C1 C6 C7 121.0(4) . .
N1 C8 C13 103.8(3) . .
N1 C8 C9 116.7(4) . .
C13 C8 C9 110.7(3) . .
N1 C8 H8 108.4 . .
C13 C8 H8 108.4 . .
C9 C8 H8 108.4 . .
O2 C20 C19 120.4(4) . .
O2 C20 C15 124.9(4) . .
C19 C20 C15 114.6(4) . .
C10 C9 C8 113.8(4) . .
C10 C9 H9A 108.8 . .
C8 C9 H9A 108.8 . .
C10 C9 H9B 108.8 . .
C8 C9 H9B 108.8 . .
H9A C9 H9B 107.7 . .
C14 N2 C13 119.4(3) . .
C14 N2 Ni1 128.0(3) . .
C13 N2 Ni1 112.4(3) . .
N2 C13 C12 109.6(4) . .
N2 C13 C8 105.5(3) . .
C12 C13 C8 112.2(3) . .
N2 C13 H13 109.8 . .
C12 C13 H13 109.8 . .
C8 C13 H13 109.8 . .
C3 C2 C1 123.5(4) . .
C3 C2 Br1 118.2(3) . .
C1 C2 Br1 118.2(3) . .
C16 C17 C18 121.1(4) . .
C16 C17 Cl2 120.8(3) . .
C18 C17 Cl2 118.1(3) . .
C10 C11 C12 110.9(4) . .
C10 C11 H11A 109.5 . .
C12 C11 H11A 109.5 . .
C10 C11 H11B 109.5 . .
C12 C11 H11B 109.5 . .
H11A C11 H11B 108.0 . .
C5 C4 C3 120.1(4) . .
C5 C4 Cl1 120.5(3) . .
C3 C4 Cl1 119.3(3) . .
C2 C3 C4 119.4(4) . .
C2 C3 H3 120.3 . .
C4 C3 H3 120.3 . .
C13 C12 C11 110.8(4) . .
C13 C12 H12A 109.5 . .
C11 C12 H12A 109.5 . .
C13 C12 H12B 109.5 . .
C11 C12 H12B 109.5 . .
H12A C12 H12B 108.1 . .
C9 C10 C11 110.8(4) . .
C9 C10 H10A 109.5 . .
C11 C10 H10A 109.5 . .
C9 C10 H10B 109.5 . .
C11 C10 H10B 109.5 . .
H10A C10 H10B 108.1 . .
C19 C18 C17 119.5(4) . .
C19 C18 H18 120.2 . .
C17 C18 H18 120.2 . .
C16 C15 C20 122.2(4) . .
C16 C15 C14 118.0(4) . .
C20 C15 C14 119.8(4) . .
C18 C19 C20 123.6(4) . .
C18 C19 Br2 118.2(3) . .
C20 C19 Br2 118.1(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Br1 C2 1.899(4) .
Ni1 O2 1.851(3) .
Ni1 O1 1.852(3) .
Ni1 N2 1.854(3) .
Ni1 N1 1.864(4) .
Br2 C19 1.887(4) .
Cl1 C4 1.745(4) .
Cl2 C17 1.750(4) .
O1 C1 1.310(5) .
O2 C20 1.298(5) .
C7 N1 1.290(5) .
C7 C6 1.440(6) .
C7 H7 0.9300 .
C14 N2 1.284(5) .
C14 C15 1.441(6) .
C14 H14 0.9300 .
C5 C4 1.366(6) .
C5 C6 1.410(6) .
C5 H5 0.9300 .
C16 C17 1.379(6) .
C16 C15 1.410(6) .
C16 H16 0.9300 .
C1 C2 1.412(6) .
C1 C6 1.416(6) .
N1 C8 1.496(5) .
C8 C13 1.523(6) .
C8 C9 1.527(6) .
C8 H8 0.9800 .
C20 C19 1.417(6) .
C20 C15 1.427(6) .
C9 C10 1.510(6) .
C9 H9A 0.9700 .
C9 H9B 0.9700 .
N2 C13 1.476(5) .
C13 C12 1.516(6) .
C13 H13 0.9800 .
C2 C3 1.365(6) .
C17 C18 1.386(6) .
C11 C10 1.527(6) .
C11 C12 1.533(6) .
C11 H11A 0.9700 .
C11 H11B 0.9700 .
C4 C3 1.390(6) .
C3 H3 0.9300 .
C12 H12A 0.9700 .
C12 H12B 0.9700 .
C10 H10A 0.9700 .
C10 H10B 0.9700 .
C18 C19 1.367(6) .
C18 H18 0.9300 .
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
O2 Ni1 O1 C1 -174.2(3) . . . .
N1 Ni1 O1 C1 8.1(3) . . . .
O1 Ni1 O2 C20 -169.4(3) . . . .
N2 Ni1 O2 C20 13.5(3) . . . .
Ni1 O1 C1 C2 177.6(3) . . . .
Ni1 O1 C1 C6 -3.6(5) . . . .
C6 C7 N1 C8 -173.3(4) . . . .
C6 C7 N1 Ni1 1.3(6) . . . .
O1 Ni1 N1 C7 -6.9(3) . . . .
N2 Ni1 N1 C7 170.2(4) . . . .
O1 Ni1 N1 C8 168.0(3) . . . .
N2 Ni1 N1 C8 -14.8(3) . . . .
C4 C5 C6 C1 0.0(6) . . . .
C4 C5 C6 C7 -175.4(4) . . . .
O1 C1 C6 C5 179.9(4) . . . .
C2 C1 C6 C5 -1.2(6) . . . .
O1 C1 C6 C7 -4.8(6) . . . .
C2 C1 C6 C7 174.0(4) . . . .
N1 C7 C6 C5 -178.6(4) . . . .
N1 C7 C6 C1 6.0(6) . . . .
C7 N1 C8 C13 -146.9(4) . . . .
Ni1 N1 C8 C13 37.8(4) . . . .
C7 N1 C8 C9 -24.9(5) . . . .
Ni1 N1 C8 C9 159.8(3) . . . .
Ni1 O2 C20 C19 168.7(3) . . . .
Ni1 O2 C20 C15 -12.0(6) . . . .
N1 C8 C9 C10 -66.1(5) . . . .
C13 C8 C9 C10 52.3(5) . . . .
C15 C14 N2 C13 -176.9(4) . . . .
C15 C14 N2 Ni1 -2.1(6) . . . .
O2 Ni1 N2 C14 -6.6(4) . . . .
N1 Ni1 N2 C14 171.1(4) . . . .
O2 Ni1 N2 C13 168.5(3) . . . .
N1 Ni1 N2 C13 -13.8(3) . . . .
C14 N2 C13 C12 92.3(5) . . . .
Ni1 N2 C13 C12 -83.3(4) . . . .
C14 N2 C13 C8 -146.7(4) . . . .
Ni1 N2 C13 C8 37.7(4) . . . .
N1 C8 C13 N2 -46.3(4) . . . .
C9 C8 C13 N2 -172.3(3) . . . .
N1 C8 C13 C12 73.0(4) . . . .
C9 C8 C13 C12 -53.0(5) . . . .
O1 C1 C2 C3 -179.8(4) . . . .
C6 C1 C2 C3 1.3(6) . . . .
O1 C1 C2 Br1 1.9(5) . . . .
C6 C1 C2 Br1 -177.0(3) . . . .
C15 C16 C17 C18 2.9(6) . . . .
C15 C16 C17 Cl2 -177.7(3) . . . .
C6 C5 C4 C3 1.2(6) . . . .
C6 C5 C4 Cl1 178.9(3) . . . .
C1 C2 C3 C4 -0.2(6) . . . .
Br1 C2 C3 C4 178.1(3) . . . .
C5 C4 C3 C2 -1.1(6) . . . .
Cl1 C4 C3 C2 -178.9(3) . . . .
N2 C13 C12 C11 173.0(3) . . . .
C8 C13 C12 C11 56.1(5) . . . .
C10 C11 C12 C13 -56.9(5) . . . .
C8 C9 C10 C11 -53.7(5) . . . .
C12 C11 C10 C9 55.2(5) . . . .
C16 C17 C18 C19 -0.8(7) . . . .
Cl2 C17 C18 C19 179.8(3) . . . .
C17 C16 C15 C20 -1.7(6) . . . .
C17 C16 C15 C14 177.7(4) . . . .
O2 C20 C15 C16 179.2(4) . . . .
C19 C20 C15 C16 -1.4(6) . . . .
O2 C20 C15 C14 -0.1(6) . . . .
C19 C20 C15 C14 179.2(4) . . . .
N2 C14 C15 C16 -171.9(4) . . . .
N2 C14 C15 C20 7.4(6) . . . .
C17 C18 C19 C20 -2.7(7) . . . .
C17 C18 C19 Br2 175.0(3) . . . .
O2 C20 C19 C18 -177.0(4) . . . .
C15 C20 C19 C18 3.7(6) . . . .
O2 C20 C19 Br2 5.3(5) . . . .
C15 C20 C19 Br2 -174.0(3) . . . .
