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#$Date: 2022-05-09 09:57:06 +0300 (Mon, 09 May 2022) $
#$Revision: 275259 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/51/8105172.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_8105172
loop_
_publ_author_name
'Li, Weili'
'Bo, Yang'
_publ_section_title
;
 Crystal structure of
 {2,2′-{cyclohexane-1,2-diylbis[(azanylylidene)methylylidene]}bis(2,4-dibromophenolato)-κ4
 N,N′,O,O′}copper(II) ─ diethylformamide (1/1),
 C23H23Br4CuN3O3
;
_journal_issue                   2
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              185
_journal_page_last               187
_journal_paper_doi               10.1515/ncrs-2021-0379
_journal_volume                  237
_journal_year                    2022
_chemical_formula_moiety         'C20 H16 Br4 Cu N2 O2, C3 H7 N O'
_chemical_formula_sum            'C23 H23 Br4 Cu N3 O3'
_chemical_formula_weight         772.62
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                98.153(2)
_cell_angle_beta                 111.484(2)
_cell_angle_gamma                105.035(2)
_cell_formula_units_Z            2
_cell_length_a                   10.4769(4)
_cell_length_b                   10.7829(5)
_cell_length_c                   12.9824(5)
_cell_measurement_reflns_used    8459
_cell_measurement_temperature    273.15
_cell_measurement_theta_max      26.42
_cell_measurement_theta_min      3.01
_cell_volume                     1271.43(10)
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.3 (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve 1.3 (Bourhis et al., 2015)'
_diffrn_ambient_temperature      273.15
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0220
_diffrn_reflns_av_unetI/netI     0.0585
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            8469
_diffrn_reflns_theta_full        26.44
_diffrn_reflns_theta_max         26.44
_diffrn_reflns_theta_min         3.01
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    7.175
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6010
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0883 before and 0.0254 after correction.
The Ratio of minimum to maximum transmission is 0.8063.
The λ/2 correction factor is 0.00150.
;
_exptl_crystal_colour            'clear blackish black'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   blackish
_exptl_crystal_colour_primary    black
_exptl_crystal_density_diffrn    2.018
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             750
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_refine_diff_density_max         1.102
_refine_diff_density_min         -1.178
_refine_diff_density_rms         0.171
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.136
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     309
_refine_ls_number_reflns         5230
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.136
_refine_ls_R_factor_all          0.0429
_refine_ls_R_factor_gt           0.0338
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0276P)²+6.0559P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0924
_refine_ls_wR_factor_ref         0.1158
_reflns_number_gt                4520
_reflns_number_total             5230
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            suppl_j_ncrs-2021-0379_suppl.cif
_cod_data_source_block           s_a
_cod_original_cell_volume        1271.43(9)
_cod_database_code               8105172
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C13(H13), C8(H8)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C10(H10A,H10B), C12(H12A,H12B), C11(H11A,H11B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C7(H7), C14(H14), C18(H18), C5(H5), C16(H16), C21(H21)
2.d Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C), C23(H23A,H23B,H23C)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, -z'
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
Br2 Br 0.63313(5) 0.23839(5) 0.73782(4) 0.01910(13) Uani 1 d . . .
Br1 Br 0.96491(6) 0.70727(5) 1.09894(4) 0.02541(14) Uani 1 d . . .
Br4 Br 0.18198(6) 0.01430(5) 0.34252(5) 0.02474(14) Uani 1 d . . .
Cu1 Cu 0.34896(6) 0.48150(6) 0.52712(5) 0.01562(15) Uani 1 d . . .
Br3 Br -0.28775(7) 0.07518(6) -0.01305(5) 0.04215(19) Uani 1 d . . .
O2 O 0.2553(4) 0.3058(3) 0.4296(3) 0.0197(7) Uani 1 d . . .
O1 O 0.4954(4) 0.4229(3) 0.6236(3) 0.0187(7) Uani 1 d . . .
N1 N 0.4484(4) 0.6665(4) 0.6160(3) 0.0163(8) Uani 1 d . . .
N2 N 0.2062(5) 0.5473(4) 0.4296(4) 0.0178(9) Uani 1 d . . .
C3 C 0.7808(6) 0.4841(5) 0.9077(4) 0.0189(10) Uani 1 d . . .
H3 H 0.8319 0.4369 0.9510 0.023 Uiso 1 calc . . R
C13 C 0.2303(5) 0.6883(4) 0.4780(4) 0.0143(9) Uani 1 d . . .
H13 H 0.1973 0.7297 0.4152 0.017 Uiso 1 calc . . R
C9 C 0.4276(6) 0.8976(5) 0.6178(5) 0.0212(11) Uani 1 d . . .
H9A H 0.4057 0.9526 0.5652 0.025 Uiso 1 calc . . R
H9B H 0.5307 0.9354 0.6685 0.025 Uiso 1 calc . . R
C4 C 0.8110(5) 0.6180(5) 0.9512(4) 0.0180(10) Uani 1 d . . .
C1 C 0.5909(6) 0.4879(5) 0.7264(4) 0.0175(10) Uani 1 d . . .
N3 N 0.2973(6) 0.3072(5) 0.7716(5) 0.0318(11) Uani 1 d . . .
C20 C 0.1406(5) 0.2638(5) 0.3338(4) 0.0161(9) Uani 1 d . . .
C7 C 0.5559(6) 0.7073(5) 0.7140(4) 0.0185(10) Uani 1 d . . .
H7 H 0.5935 0.7983 0.7484 0.022 Uiso 1 calc . . R
C8 C 0.3952(5) 0.7578(5) 0.5499(4) 0.0153(9) Uani 1 d . . .
H8 H 0.4406 0.7662 0.4961 0.018 Uiso 1 calc . . R
C19 C 0.0851(5) 0.1270(5) 0.2726(4) 0.0154(9) Uani 1 d . . .
C2 C 0.6729(5) 0.4218(5) 0.7982(4) 0.0165(10) Uani 1 d . . .
C15 C 0.0592(5) 0.3421(5) 0.2807(4) 0.0155(9) Uani 1 d . . .
C6 C 0.6252(5) 0.6240(4) 0.7768(4) 0.0139(9) Uani 1 d . . .
C14 C 0.0969(5) 0.4817(5) 0.3332(4) 0.0167(10) Uani 1 d . . .
H14 H 0.0384 0.5271 0.2949 0.020 Uiso 1 calc . . R
C18 C -0.0358(6) 0.0709(5) 0.1701(4) 0.0196(10) Uani 1 d . . .
H18 H -0.0662 -0.0188 0.1330 0.023 Uiso 1 calc . . R
O3 O 0.2322(6) 0.4707(5) 0.6960(6) 0.0577(15) Uani 1 d . . .
C10 C 0.3399(6) 0.9002(5) 0.6886(5) 0.0223(11) Uani 1 d . . .
H10A H 0.3660 0.8503 0.7449 0.027 Uiso 1 calc . . R
H10B H 0.3625 0.9914 0.7293 0.027 Uiso 1 calc . . R
C5 C 0.7374(5) 0.6894(5) 0.8889(4) 0.0178(10) Uani 1 d . . .
H5 H 0.7606 0.7799 0.9194 0.021 Uiso 1 calc . . R
C17 C -0.1118(6) 0.1533(5) 0.1234(4) 0.0244(11) Uani 1 d . . .
C12 C 0.1428(6) 0.6958(5) 0.5493(5) 0.0233(11) Uani 1 d . . .
H12A H 0.0394 0.6575 0.4994 0.028 Uiso 1 calc . . R
H12B H 0.1655 0.6445 0.6050 0.028 Uiso 1 calc . . R
C11 C 0.1789(6) 0.8403(5) 0.6115(5) 0.0221(11) Uani 1 d . . .
H11A H 0.1524 0.8910 0.5558 0.026 Uiso 1 calc . . R
H11B H 0.1235 0.8438 0.6568 0.026 Uiso 1 calc . . R
C16 C -0.0666(6) 0.2866(6) 0.1770(4) 0.0226(11) Uani 1 d . . .
H16 H -0.1192 0.3394 0.1447 0.027 Uiso 1 calc . . R
C24 C 0.3728(8) 0.2668(7) 0.8723(6) 0.0367(15) Uani 1 d . . .
H24A H 0.3045 0.1961 0.8821 0.055 Uiso 1 calc . . GR
H24B H 0.4166 0.3412 0.9388 0.055 Uiso 1 calc . . GR
H24C H 0.4471 0.2365 0.8626 0.055 Uiso 1 calc . . GR
C23 C 0.2168(7) 0.2056(7) 0.6616(6) 0.0412(16) Uani 1 d . . .
H23A H 0.2843 0.1784 0.6379 0.062 Uiso 1 calc . . GR
H23B H 0.1608 0.2417 0.6049 0.062 Uiso 1 calc . . GR
H23C H 0.1526 0.1301 0.6701 0.062 Uiso 1 calc . . GR
C21 C 0.2945(8) 0.4308(7) 0.7783(7) 0.0433(17) Uani 1 d . . .
H21 H 0.3429 0.4913 0.8503 0.052 Uiso 1 calc . . R
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'
Cu Cu 0.3201 1.2651 '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'
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 O1 88.69(15) . .
O2 Cu1 N1 174.92(16) . .
O2 Cu1 N2 92.95(17) . .
O1 Cu1 N1 93.34(16) . .
O1 Cu1 N2 177.72(18) . .
N2 Cu1 N1 84.90(18) . .
C20 O2 Cu1 127.5(3) . .
C1 O1 Cu1 125.7(3) . .
C7 N1 Cu1 125.2(4) . .
C7 N1 C8 122.9(4) . .
C8 N1 Cu1 111.6(3) . .
C13 N2 Cu1 113.0(3) . .
C14 N2 Cu1 127.3(4) . .
C14 N2 C13 119.7(4) . .
C4 C3 C2 118.5(5) . .
N2 C13 C8 107.4(4) . .
N2 C13 C12 109.3(4) . .
C12 C13 C8 112.5(4) . .
C8 C9 C10 112.4(4) . .
C3 C4 Br1 119.1(4) . .
C5 C4 Br1 119.1(4) . .
C5 C4 C3 121.7(5) . .
O1 C1 C2 119.8(4) . .
O1 C1 C6 125.4(4) . .
C6 C1 C2 114.8(4) . .
C24 N3 C23 117.9(5) . .
C21 N3 C24 121.8(6) . .
C21 N3 C23 120.2(6) . .
O2 C20 C19 119.4(4) . .
O2 C20 C15 125.9(4) . .
C15 C20 C19 114.6(4) . .
N1 C7 C6 125.7(5) . .
N1 C8 C13 107.0(4) . .
N1 C8 C9 116.9(4) . .
C9 C8 C13 110.9(4) . .
C20 C19 Br4 117.0(3) . .
C18 C19 Br4 118.3(4) . .
C18 C19 C20 124.7(5) . .
C3 C2 Br2 118.4(4) . .
C3 C2 C1 123.9(5) . .
C1 C2 Br2 117.7(4) . .
C20 C15 C14 122.0(4) . .
C16 C15 C20 121.8(5) . .
C16 C15 C14 116.2(4) . .
C1 C6 C7 121.9(4) . .
C1 C6 C5 121.7(4) . .
C5 C6 C7 116.3(4) . .
N2 C14 C15 124.3(4) . .
C19 C18 C17 117.7(5) . .
C11 C10 C9 110.1(4) . .
C4 C5 C6 119.4(5) . .
C18 C17 Br3 118.4(4) . .
C16 C17 Br3 119.8(4) . .
C16 C17 C18 121.6(5) . .
C11 C12 C13 110.5(4) . .
C10 C11 C12 109.6(4) . .
C17 C16 C15 119.6(5) . .
O3 C21 N3 124.7(8) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Br2 C2 1.895(5) .
Br1 C4 1.900(5) .
Br4 C19 1.900(5) .
Cu1 O2 1.898(4) .
Cu1 O1 1.908(3) .
Cu1 N1 1.945(4) .
Cu1 N2 1.940(4) .
Br3 C17 1.904(5) .
O2 C20 1.288(6) .
O1 C1 1.290(6) .
N1 C7 1.271(7) .
N1 C8 1.480(6) .
N2 C13 1.478(6) .
N2 C14 1.286(6) .
C3 C4 1.381(7) .
C3 C2 1.381(7) .
C13 C8 1.538(6) .
C13 C12 1.530(7) .
C9 C8 1.517(7) .
C9 C10 1.522(7) .
C4 C5 1.367(7) .
C1 C2 1.426(7) .
C1 C6 1.412(7) .
N3 C24 1.452(8) .
N3 C23 1.464(9) .
N3 C21 1.332(8) .
C20 C19 1.424(7) .
C20 C15 1.424(7) .
C7 C6 1.453(7) .
C19 C18 1.371(7) .
C15 C14 1.446(7) .
C15 C16 1.404(7) .
C6 C5 1.422(7) .
C18 C17 1.400(7) .
O3 C21 1.232(9) .
C10 C11 1.510(7) .
C17 C16 1.377(8) .
C12 C11 1.529(7) .
