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#$Date: 2023-07-05 13:30:51 +0300 (Wed, 05 Jul 2023) $
#$Revision: 284932 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/06/24/7062467.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_7062467
loop_
_publ_author_name
'Mahmudov, Ibadulla'
'Gurbanov, Atash V.'
'Martins, Luísa M. D. R. S.'
'Abdullayev, Yusif'
'Sujayev, Afsun'
'Mahmudov, Kamran T.'
'Pombeiro, Armando J. L.'
_publ_section_title
;
 Co(ii/iii), Ni(ii) and Cu(ii) complexes with a pyrazole-functionalized
 1,3,5-triazopentadiene: synthesis, structure and application in the
 oxidation of styrene to benzaldehyde
;
_journal_issue                   22
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              10826
_journal_page_last               10833
_journal_paper_doi               10.1039/D3NJ01120H
_journal_volume                  47
_journal_year                    2023
_chemical_formula_moiety         'C10 H14 N12 Ni'
_chemical_formula_sum            'C10 H14 N12 Ni'
_chemical_formula_weight         361.04
_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   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   direct
_audit_creation_method           SHELXL-2019/1
_audit_update_record
;
2022-07-31 deposited with the CCDC.	2023-05-05 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 116.167(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   12.2955(8)
_cell_length_b                   4.9045(3)
_cell_length_c                   13.1699(9)
_cell_measurement_reflns_used    8401
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      26.37
_cell_measurement_theta_min      3.69
_cell_volume                     712.79(8)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX3'
_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 0.991
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker D8 Quest PHOTON 100 detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0185
_diffrn_reflns_av_unetI/netI     0.0096
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            13009
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.374
_diffrn_reflns_theta_min         3.693
_exptl_absorpt_coefficient_mu    1.383
_exptl_absorpt_correction_T_max  0.846
_exptl_absorpt_correction_T_min  0.683
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2008)'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.682
_exptl_crystal_description       plate
_exptl_crystal_F_000             372
_exptl_crystal_size_max          0.270
_exptl_crystal_size_mid          0.230
_exptl_crystal_size_min          0.110
_refine_diff_density_max         0.268
_refine_diff_density_min         -0.257
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     118
_refine_ls_number_reflns         1447
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.074
_refine_ls_R_factor_all          0.0239
_refine_ls_R_factor_gt           0.0205
_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)+(0.0135P)²+0.7183P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0473
_refine_ls_wR_factor_ref         0.0500
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1317
_reflns_number_total             1447
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3nj01120h2.cif
_cod_data_source_block           MEP272_A
_cod_depositor_comments
'Adding full bibliography for 7062466--7062469.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7062467
_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   0.706
_shelx_estimated_absorpt_t_max   0.863
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
Ni1 Ni 0.500000 0.000000 0.500000 0.01465(9) Uani 1 2 d S . P . .
N1 N 0.45904(11) -0.1168(3) 0.61336(10) 0.0183(3) Uani 1 1 d D . . . .
H1N H 0.4956(16) -0.260(3) 0.6518(14) 0.022 Uiso 1 1 d D U . . .
N2 N 0.29683(11) 0.1832(3) 0.58819(10) 0.0187(3) Uani 1 1 d . . . . .
N3 N 0.21010(11) 0.5001(3) 0.44669(10) 0.0178(3) Uani 1 1 d . . . . .
N4 N 0.19756(12) 0.6280(3) 0.35042(11) 0.0238(3) Uani 1 1 d . . . . .
N5 N 0.36225(12) -0.1294(3) 0.73069(11) 0.0217(3) Uani 1 1 d D . . . .
H5A H 0.2947(14) -0.098(4) 0.7334(15) 0.026 Uiso 1 1 d D U . . .
H5B H 0.3984(16) -0.282(3) 0.7591(15) 0.026 Uiso 1 1 d D U . . .
N6 N 0.62298(12) -0.2564(3) 0.54462(11) 0.0197(3) Uani 1 1 d D . . . .
H6N H 0.6360(16) -0.365(4) 0.6001(14) 0.024 Uiso 1 1 d D U . . .
C1 C 0.37394(13) -0.0236(3) 0.63972(12) 0.0168(3) Uani 1 1 d . . . . .
C2 C 0.30222(13) 0.2991(3) 0.49935(12) 0.0169(3) Uani 1 1 d . . . . .
C3 C 0.10671(14) 0.8009(4) 0.32699(14) 0.0254(3) Uani 1 1 d . . . . .
H3 H 0.077246 0.921477 0.264105 0.030 Uiso 1 1 calc R U . . .
C4 C 0.05916(14) 0.7845(4) 0.40625(14) 0.0246(3) Uani 1 1 d . . . . .
H4 H -0.006180 0.886224 0.407094 0.030 Uiso 1 1 calc R U . . .
C5 C 0.12746(14) 0.5903(4) 0.48176(13) 0.0218(3) Uani 1 1 d . . . . .
H5 H 0.118963 0.529658 0.546402 0.026 Uiso 1 1 calc R U . . .
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'
Ni Ni 0.3393 1.1124 '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
N6 Ni1 N6 180.0 . 3_656 ?
N6 Ni1 N1 90.48(6) . . ?
N6 Ni1 N1 89.52(6) 3_656 . ?
N6 Ni1 N1 89.52(6) . 3_656 ?
N6 Ni1 N1 90.48(6) 3_656 3_656 ?
N1 Ni1 N1 180.00(3) . 3_656 ?
C1 N1 Ni1 129.00(11) . . ?
C1 N1 H1N 113.1(12) . . ?
Ni1 N1 H1N 117.6(12) . . ?
C2 N2 C1 117.89(12) . . ?
N4 N3 C5 111.79(13) . . ?
N4 N3 C2 120.66(12) . . ?
C5 N3 C2 127.55(13) . . ?
C3 N4 N3 104.43(12) . . ?
C1 N5 H5A 116.3(13) . . ?
C1 N5 H5B 118.2(13) . . ?
H5A N5 H5B 117.2(18) . . ?
C2 N6 Ni1 127.32(11) 3_656 . ?
C2 N6 H6N 112.1(13) 3_656 . ?
Ni1 N6 H6N 120.6(12) . . ?
N1 C1 N2 126.17(14) . . ?
N1 C1 N5 119.98(14) . . ?
N2 C1 N5 113.77(13) . . ?
N6 C2 N2 129.96(14) 3_656 . ?
N6 C2 N3 117.34(13) 3_656 . ?
N2 C2 N3 112.70(12) . . ?
N4 C3 C4 111.98(15) . . ?
N4 C3 H3 124.0 . . ?
C4 C3 H3 124.0 . . ?
C5 C4 C3 104.90(14) . . ?
C5 C4 H4 127.6 . . ?
C3 C4 H4 127.6 . . ?
N3 C5 C4 106.90(14) . . ?
N3 C5 H5 126.6 . . ?
C4 C5 H5 126.6 . . ?
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
Ni1 N6 1.8519(13) . ?
Ni1 N6 1.8519(13) 3_656 ?
Ni1 N1 1.8638(12) . ?
Ni1 N1 1.8638(12) 3_656 ?
N1 C1 1.3208(19) . ?
N1 H1N 0.866(14) . ?
N2 C2 1.3285(19) . ?
N2 C1 1.349(2) . ?
N3 N4 1.3610(18) . ?
N3 C5 1.3621(19) . ?
N3 C2 1.4292(19) . ?
N4 C3 1.326(2) . ?
N5 C1 1.3700(19) . ?
N5 H5A 0.861(14) . ?
N5 H5B 0.868(15) . ?
N6 C2 1.3018(19) 3_656 ?
N6 H6N 0.859(15) . ?
C3 C4 1.406(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.366(2) . ?
C4 H4 0.9500 . ?
C5 H5 0.9500 . ?
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 N5 0.866(14) 2.519(15) 3.374(2) 169.2(16) 2_646 yes
N5 H5A N4 0.861(14) 2.334(16) 3.0665(18) 143.1(16) 4_566 yes
N5 H5B N1 0.868(15) 2.447(16) 3.2835(19) 161.9(17) 2_646 yes
N6 H6N N4 0.859(15) 2.260(18) 2.7223(19) 113.8(15) 3_656 yes
N6 H6N N5 0.859(15) 2.571(15) 3.4150(19) 167.6(17) 2_646 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
N6 Ni1 N1 C1 178.91(14) . . . . ?
N6 Ni1 N1 C1 -1.09(14) 3_656 . . . ?
C5 N3 N4 C3 0.63(18) . . . . ?
C2 N3 N4 C3 -178.94(14) . . . . ?
N1 Ni1 N6 C2 -179.80(14) . . . 3_656 ?
N1 Ni1 N6 C2 0.20(14) 3_656 . . 3_656 ?
Ni1 N1 C1 N2 -0.2(2) . . . . ?
Ni1 N1 C1 N5 -176.65(11) . . . . ?
C2 N2 C1 N1 3.1(2) . . . . ?
C2 N2 C1 N5 179.68(13) . . . . ?
C1 N2 C2 N6 -4.7(2) . . . 3_656 ?
C1 N2 C2 N3 175.32(13) . . . . ?
N4 N3 C2 N6 3.9(2) . . . 3_656 ?
C5 N3 C2 N6 -175.57(15) . . . 3_656 ?
N4 N3 C2 N2 -176.08(13) . . . . ?
C5 N3 C2 N2 4.4(2) . . . . ?
N3 N4 C3 C4 -0.69(19) . . . . ?
N4 C3 C4 C5 0.5(2) . . . . ?
N4 N3 C5 C4 -0.34(19) . . . . ?
C2 N3 C5 C4 179.20(14) . . . . ?
C3 C4 C5 N3 -0.09(18) . . . . ?
