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#$Date: 2023-09-05 23:11:13 +0300 (Tue, 05 Sep 2023) $
#$Revision: 286175 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/06/26/7062625.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_7062625
loop_
_publ_author_name
'Garazade, Ismayil M.'
'Gurbanov, Atash V.'
'Gomila, Rosa M.'
'Frontera, Antonio'
'Nunes, Ana V. M.'
'Mahmudov, Kamran T.'
'Pombeiro, Armando J. L.'
_publ_section_title
;
 Spodium, halogen and hydrogen bonds in the reactivity of
 bis(2,4-bis(trichloromethyl)-1,3,5-triazapentadienato)-Zn(ii)
;
_journal_issue                   34
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              15856
_journal_page_last               15861
_journal_paper_doi               10.1039/D3NJ02994H
_journal_volume                  47
_journal_year                    2023
_chemical_formula_moiety         'C8 H4 Cl12 Cu N6, 2(C3 H6 O)'
_chemical_formula_sum            'C14 H16 Cl12 Cu N6 O2'
_chemical_formula_weight         789.27
_space_group_crystal_system      monoclinic
_space_group_IT_number           12
_space_group_name_Hall           '-C 2y'
_space_group_name_H-M_alt        'C 1 2/m 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2019/1
_audit_update_record
;
2023-04-18 deposited with the CCDC.	2023-08-01 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 119.710(15)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   12.961(4)
_cell_length_b                   9.431(3)
_cell_length_c                   13.904(4)
_cell_measurement_reflns_used    4669
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      26.11
_cell_measurement_theta_min      2.78
_cell_volume                     1476.1(8)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX4'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_structure_solution    'SHELXT 2019/1 (Sheldrick, 2019)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.924
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0310
_diffrn_reflns_av_unetI/netI     0.0242
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.924
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            8850
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.924
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.190
_diffrn_reflns_theta_min         2.785
_exptl_absorpt_coefficient_mu    1.852
_exptl_absorpt_correction_T_max  0.805
_exptl_absorpt_correction_T_min  0.653
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2008)'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.776
_exptl_crystal_description       plate
_exptl_crystal_F_000             782
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.110
_refine_diff_density_max         0.326
_refine_diff_density_min         -0.289
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     142
_refine_ls_number_reflns         1616
_refine_ls_number_restraints     32
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0311
_refine_ls_R_factor_gt           0.0232
_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)+(0.0193P)²+1.5454P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0497
_refine_ls_wR_factor_ref         0.0526
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1383
_reflns_number_total             1616
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3nj02994h2.cif
_cod_data_source_block           cu1
_cod_depositor_comments
'Adding full bibliography for 7062625--7062628.cif.'
_cod_original_sg_symbol_H-M      'C 2/m'
_cod_database_code               7062625
_shelx_shelxl_version_number     2019/1
_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   0.645
_shelx_estimated_absorpt_t_max   0.822
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x, -y, z'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, 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_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 0.000000 0.000000 1.000000 0.02022(12) Uani 1 4 d S T P B .
C3 C 0.1656(3) 0.0177(13) 1.3570(2) 0.0232(18) Uani 0.5 1 d D . P A -1
Cl1 Cl 0.2526(5) 0.1666(5) 1.3683(4) 0.0317(6) Uani 0.5 1 d D . P A -1
Cl2 Cl 0.11199(8) 0.03471(15) 1.45515(7) 0.0442(6) Uani 0.5 1 d D . P A -1
Cl3 Cl 0.2528(5) -0.1361(5) 1.3884(4) 0.0415(8) Uani 0.5 1 d D . P A -1
C4 C -0.2454(2) 0.000000 1.13602(19) 0.0213(5) Uani 1 2 d DS T P . .
Cl4 Cl -0.22847(7) 0.0146(14) 1.27194(7) 0.0413(15) Uani 0.5 1 d D . P B -1
Cl5 Cl -0.3156(6) -0.1609(6) 1.0809(4) 0.0365(8) Uani 0.5 1 d D . P B -1
Cl6 Cl -0.3350(6) 0.1416(6) 1.0558(5) 0.0396(10) Uani 0.5 1 d D . P B -1
N1 N -0.09883(17) 0.000000 0.84199(16) 0.0287(5) Uani 1 2 d S T P . .
H1N H -0.177441 0.000000 0.820171 0.034 Uiso 1 2 d R U P . .
N2 N -0.03769(16) 0.000000 1.22856(15) 0.0199(4) Uani 1 2 d S T P . .
N3 N -0.13155(17) 0.000000 1.03319(16) 0.0271(5) Uani 1 2 d S T P . .
H3N H -0.203604 0.000000 0.975608 0.033 Uiso 1 2 d R U P B .
C1 C 0.0681(2) 0.000000 1.23613(18) 0.0203(5) Uani 1 2 d S T P A .
C2 C -0.12897(19) 0.000000 1.12961(19) 0.0180(5) Uani 1 2 d S T P B .
O1 O 0.3361(2) 0.9575(3) 0.1856(2) 0.0467(12) Uani 0.5 1 d D . P C -1
C5 C 0.4341(3) 0.9872(15) 0.2505(3) 0.0334(15) Uani 0.5 1 d D . P C -1
C6 C 0.4818(5) 1.1299(7) 0.2555(6) 0.0653(18) Uani 0.5 1 d D . P C -1
H6A H 0.511502 1.169278 0.329807 0.098 Uiso 0.5 1 calc R U P C -1
H6B H 0.418796 1.191053 0.200977 0.098 Uiso 0.5 1 calc R U P C -1
H6C H 0.546912 1.124515 0.238910 0.098 Uiso 0.5 1 calc R U P C -1
C7 C 0.5106(6) 0.8801(8) 0.3304(6) 0.078(2) Uani 0.5 1 d D . P C -1
H7A H 0.581752 0.866565 0.323756 0.117 Uiso 0.5 1 calc R U P C -1
H7B H 0.467245 0.790231 0.315266 0.117 Uiso 0.5 1 calc R U P C -1
H7C H 0.533834 0.911798 0.405548 0.117 Uiso 0.5 1 calc R U P C -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'
Cl Cl 0.1484 0.1585 '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
_geom_angle_publ_flag
N1 Cu1 N1 180.0 . 5_557 ?
N1 Cu1 N3 84.04(9) . 5_557 ?
N1 Cu1 N3 95.96(9) 5_557 5_557 ?
N1 Cu1 N3 95.96(9) . . ?
N1 Cu1 N3 84.04(9) 5_557 . ?
N3 Cu1 N3 180.0 5_557 . ?
C1 C3 Cl3 105.2(6) . . ?
C1 C3 Cl1 109.2(5) . . ?
Cl3 C3 Cl1 109.37(17) . . ?
C1 C3 Cl2 114.8(2) . . ?
Cl3 C3 Cl2 108.9(4) . . ?
Cl1 C3 Cl2 109.2(5) . . ?
C2 C4 Cl5 106.6(3) . . ?
C2 C4 Cl6 108.6(3) . . ?
Cl5 C4 Cl6 110.28(15) . . ?
C2 C4 Cl4 116.37(16) . . ?
Cl5 C4 Cl4 107.1(4) . . ?
Cl6 C4 Cl4 107.9(4) . . ?
C1 N1 Cu1 129.45(16) 5_557 . ?
C1 N1 H1N 117.9 5_557 . ?
Cu1 N1 H1N 112.6 . . ?
C2 N2 C1 116.7(2) . . ?
C2 N3 Cu1 130.16(16) . . ?
C2 N3 H3N 113.9 . . ?
Cu1 N3 H3N 116.0 . . ?
N2 C1 N1 130.8(2) . 5_557 ?
N2 C1 C3 110.3(2) . . ?
N1 C1 C3 118.6(2) 5_557 . ?
N2 C2 N3 128.8(2) . . ?
N2 C2 C4 109.90(19) . . ?
N3 C2 C4 121.3(2) . . ?
O1 C5 C7 119.2(10) . . ?
O1 C5 C6 121.7(8) . . ?
C7 C5 C6 119.1(5) . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C5 C7 H7A 109.5 . . ?
C5 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C5 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 N1 1.918(2) . ?
Cu1 N1 1.918(2) 5_557 ?
Cu1 N3 1.975(2) 5_557 ?
Cu1 N3 1.975(2) . ?
C3 C1 1.531(4) . ?
C3 Cl3 1.757(10) . ?
C3 Cl1 1.758(9) . ?
C3 Cl2 1.819(3) . ?
C4 C2 1.555(3) . ?
C4 Cl5 1.740(6) . ?
C4 Cl6 1.758(6) . ?
C4 Cl4 1.796(3) . ?
N1 C1 1.330(3) 5_557 ?
N1 H1N 0.9076 . ?
N2 C2 1.296(3) . ?
N2 C1 1.322(3) . ?
N3 C2 1.324(3) . ?
N3 H3N 0.8786 . ?
O1 C5 1.170(5) . ?
C5 C7 1.464(10) . ?
C5 C6 1.468(12) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
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
_geom_hbond_publ_flag
N1 H1N O1^a 0.91 2.06 2.932(3) 161.4 5_566 yes
N1 H1N O1^a 0.91 2.06 2.932(3) 161.4 2_546 yes
N3 H3N O1^a 0.88 2.08 2.907(3) 156.9 5_566 yes
N3 H3N O1^a 0.88 2.08 2.907(3) 156.9 2_546 yes
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
_geom_torsion_publ_flag
C2 N2 C1 N1 0.000(3) . . . 5_557 ?
C2 N2 C1 C3 173.3(5) . . . . ?
Cl3 C3 C1 N2 119.3(2) . . . . ?
Cl1 C3 C1 N2 -123.4(3) . . . . ?
Cl2 C3 C1 N2 -0.4(8) . . . . ?
Cl3 C3 C1 N1 -66.4(5) . . . 5_557 ?
Cl1 C3 C1 N1 50.9(6) . . . 5_557 ?
Cl2 C3 C1 N1 173.9(4) . . . 5_557 ?
C1 N2 C2 N3 0.000(2) . . . . ?
C1 N2 C2 C4 180.000(2) . . . . ?
Cu1 N3 C2 N2 0.000(2) . . . . ?
Cu1 N3 C2 C4 180.000(1) . . . . ?
Cl5 C4 C2 N2 -114.5(2) . . . . ?
Cl6 C4 C2 N2 126.8(2) . . . . ?
Cl4 C4 C2 N2 4.9(5) . . . . ?
Cl5 C4 C2 N3 65.5(2) . . . . ?
Cl6 C4 C2 N3 -53.2(2) . . . . ?
Cl4 C4 C2 N3 -175.1(5) . . . . ?
