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#$Date: 2022-06-10 11:43:07 +0300 (Fri, 10 Jun 2022) $
#$Revision: 275957 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/53/8105378.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_8105378
loop_
_publ_author_name
'Li, Li'
_publ_section_title
;
 Crystal structure of
 bis[3-methoxy-N-(1-(pyrazin-2-yl)ethylidene)benzohydrazonato-κ3
 O,N,N′]nickel(II), C28H26N8O4Ni
;
_journal_issue                   5
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              1063
_journal_page_last               1064
_journal_paper_doi               10.1515/ncrs-2020-0170
_journal_volume                  235
_journal_year                    2020
_chemical_formula_sum            'C28 H26 N8 Ni O4'
_chemical_formula_weight         597.28
_space_group_crystal_system      orthorhombic
_space_group_IT_number           60
_space_group_name_Hall           '-P 2n 2ab'
_space_group_name_H-M_alt        'P b c n'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.675(9)
_cell_length_b                   9.884(8)
_cell_length_c                   23.225(17)
_cell_measurement_reflns_used    1570
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      21.78
_cell_measurement_theta_min      2.70
_cell_volume                     2680(4)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.0775
_diffrn_reflns_av_unetI/netI     0.0722
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            12403
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        24.989
_diffrn_reflns_theta_max         24.989
_diffrn_reflns_theta_min         1.754
_exptl_absorpt_coefficient_mu    0.775
_exptl_absorpt_correction_T_max  0.925
_exptl_absorpt_correction_T_min  0.900
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    1.480
_exptl_crystal_description       block
_exptl_crystal_F_000             1240
_exptl_crystal_size_max          0.140
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.386
_refine_diff_density_min         -0.326
_refine_diff_density_rms         0.064
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     188
_refine_ls_number_reflns         2350
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.0853
_refine_ls_R_factor_gt           0.0495
_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)+(0.0465P)²+2.3192P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1141
_refine_ls_wR_factor_ref         0.1329
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1548
_reflns_number_total             2350
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_ncrs-2020-0170_suppl.cif
_cod_data_source_block           1
_cod_database_code               8105378
_shelx_shelxl_version_number     2014/7
_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   0.899
_shelx_estimated_absorpt_t_max   0.926
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'-x, y, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'x, -y, z-1/2'
'-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
Ni1 Ni 0.5000 0.10103(8) 0.2500 0.0385(2) Uani 1 2 d S T P . .
O1 O 0.4855(2) 0.2411(3) 0.18343(11) 0.0443(7) Uani 1 1 d . . . . .
O2 O 0.1264(3) 0.3301(3) 0.00923(13) 0.0678(10) Uani 1 1 d . . . . .
N1 N 0.4385(3) -0.0470(3) 0.30800(13) 0.0430(8) Uani 1 1 d . . . . .
N2 N 0.3241(3) -0.2329(4) 0.37682(16) 0.0640(11) Uani 1 1 d . . . . .
N3 N 0.3356(3) 0.0996(3) 0.23360(12) 0.0379(8) Uani 1 1 d . . . . .
N4 N 0.2944(2) 0.1812(3) 0.19036(13) 0.0406(8) Uani 1 1 d . . . . .
C1 C 0.4941(4) -0.1253(5) 0.34492(18) 0.0542(11) Uani 1 1 d . . . . .
H1 H 0.5734 -0.1188 0.3476 0.065 Uiso 1 1 calc R U . . .
C2 C 0.4372(4) -0.2155(5) 0.3792(2) 0.0656(14) Uani 1 1 d . . . . .
H2 H 0.4792 -0.2669 0.4052 0.079 Uiso 1 1 calc R U . . .
C3 C 0.2690(4) -0.1549(5) 0.33907(18) 0.0529(11) Uani 1 1 d . . . . .
H3 H 0.1901 -0.1642 0.3357 0.063 Uiso 1 1 calc R U . . .
C4 C 0.3235(3) -0.0612(4) 0.30484(16) 0.0387(9) Uani 1 1 d . . . . .
C5 C 0.2656(3) 0.0260(4) 0.26297(15) 0.0383(9) Uani 1 1 d . . . . .
C6 C 0.1402(3) 0.0258(5) 0.25562(18) 0.0497(11) Uani 1 1 d . . . . .
H6A H 0.1121 0.1170 0.2575 0.074 Uiso 1 1 calc R U . . .
H6B H 0.1057 -0.0269 0.2857 0.074 Uiso 1 1 calc R U . . .
H6C H 0.1211 -0.0128 0.2189 0.074 Uiso 1 1 calc R U . . .
C7 C 0.3822(3) 0.2456(4) 0.16586(16) 0.0393(9) Uani 1 1 d . . . . .
C8 C 0.3525(3) 0.3256(4) 0.11449(15) 0.0396(9) Uani 1 1 d . . . . .
C9 C 0.2547(3) 0.2971(4) 0.08416(16) 0.0433(10) Uani 1 1 d . . . . .
H9 H 0.2067 0.2282 0.0969 0.052 Uiso 1 1 calc R U . . .
C10 C 0.2259(4) 0.3687(4) 0.03504(17) 0.0486(11) Uani 1 1 d . . . . .
C11 C 0.2960(4) 0.4720(5) 0.01621(19) 0.0541(12) Uani 1 1 d . . . . .
H11 H 0.2772 0.5218 -0.0164 0.065 Uiso 1 1 calc R U . . .
C12 C 0.3942(4) 0.4999(5) 0.04672(18) 0.0538(11) Uani 1 1 d . . . . .
H12 H 0.4421 0.5690 0.0341 0.065 Uiso 1 1 calc R U . . .
C13 C 0.4234(4) 0.4292(4) 0.09489(18) 0.0490(11) Uani 1 1 d . . . . .
H13 H 0.4904 0.4500 0.1146 0.059 Uiso 1 1 calc R U . . .
C14 C 0.0965(4) 0.3910(6) -0.04418(19) 0.0753(16) Uani 1 1 d . . . . .
H14A H 0.1565 0.3755 -0.0717 0.113 Uiso 1 1 calc R U . . .
H14B H 0.0865 0.4866 -0.0388 0.113 Uiso 1 1 calc R U . . .
H14C H 0.0265 0.3522 -0.0581 0.113 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'
O O 0.0106 0.0060 '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
N3 Ni1 N3 179.2(2) . 3_655
N3 Ni1 O1 103.24(11) . 3_655
N3 Ni1 O1 77.34(11) 3_655 3_655
N3 Ni1 O1 77.34(11) . .
N3 Ni1 O1 103.24(11) 3_655 .
O1 Ni1 O1 96.65(16) 3_655 .
N3 Ni1 N1 101.78(13) . 3_655
N3 Ni1 N1 77.62(12) 3_655 3_655
O1 Ni1 N1 154.89(11) 3_655 3_655
O1 Ni1 N1 90.84(13) . 3_655
N3 Ni1 N1 77.62(12) . .
N3 Ni1 N1 101.78(13) 3_655 .
O1 Ni1 N1 90.84(13) 3_655 .
O1 Ni1 N1 154.89(11) . .
N1 Ni1 N1 92.43(19) 3_655 .
C7 O1 Ni1 109.7(2) . .
C10 O2 C14 118.3(4) . .
C1 N1 C4 117.4(4) . .
C1 N1 Ni1 130.5(3) . .
C4 N1 Ni1 112.0(2) . .
C2 N2 C3 115.5(4) . .
C5 N3 N4 119.7(3) . .
C5 N3 Ni1 121.5(3) . .
N4 N3 Ni1 118.8(2) . .
C7 N4 N3 108.8(3) . .
N1 C1 C2 121.3(4) . .
N1 C1 H1 119.3 . .
C2 C1 H1 119.3 . .
N2 C2 C1 122.8(4) . .
N2 C2 H2 118.6 . .
C1 C2 H2 118.6 . .
N2 C3 C4 123.1(4) . .
N2 C3 H3 118.4 . .
C4 C3 H3 118.4 . .
N1 C4 C3 119.9(4) . .
N1 C4 C5 115.7(3) . .
C3 C4 C5 124.5(4) . .
N3 C5 C4 113.0(3) . .
N3 C5 C6 124.7(4) . .
C4 C5 C6 122.3(3) . .
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 . .
O1 C7 N4 125.1(3) . .
O1 C7 C8 120.0(3) . .
N4 C7 C8 114.9(3) . .
C9 C8 C13 118.6(4) . .
C9 C8 C7 120.1(3) . .
C13 C8 C7 121.3(3) . .
C8 C9 C10 121.4(4) . .
C8 C9 H9 119.3 . .
C10 C9 H9 119.3 . .
O2 C10 C11 125.0(4) . .
O2 C10 C9 115.3(4) . .
C11 C10 C9 119.7(4) . .
C12 C11 C10 118.6(4) . .
C12 C11 H11 120.7 . .
C10 C11 H11 120.7 . .
C13 C12 C11 121.9(4) . .
C13 C12 H12 119.0 . .
C11 C12 H12 119.0 . .
C12 C13 C8 119.8(4) . .
C12 C13 H13 120.1 . .
C8 C13 H13 120.1 . .
O2 C14 H14A 109.5 . .
O2 C14 H14B 109.5 . .
H14A C14 H14B 109.5 . .
O2 C14 H14C 109.5 . .
H14A C14 H14C 109.5 . .
H14B C14 H14C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Ni1 N3 1.956(3) .
Ni1 N3 1.956(3) 3_655
Ni1 O1 2.082(3) 3_655
Ni1 O1 2.082(3) .
Ni1 N1 2.115(3) 3_655
Ni1 N1 2.115(3) .
O1 C7 1.275(4) .
O2 C10 1.362(5) .
O2 C14 1.423(5) .
N1 C1 1.325(5) .
N1 C4 1.351(5) .
N2 C2 1.333(6) .
N2 C3 1.333(5) .
N3 C5 1.290(5) .
N3 N4 1.376(4) .
N4 C7 1.333(5) .
C1 C2 1.367(6) .
C1 H1 0.9300 .
C2 H2 0.9300 .
C3 C4 1.376(5) .
C3 H3 0.9300 .
C4 C5 1.465(5) .
C5 C6 1.475(5) .
C6 H6A 0.9600 .
C6 H6B 0.9600 .
C6 H6C 0.9600 .
C7 C8 1.473(5) .
C8 C9 1.371(5) .
C8 C13 1.393(5) .
C9 C10 1.384(5) .
C9 H9 0.9300 .
C10 C11 1.380(6) .
C11 C12 1.376(6) .
C11 H11 0.9300 .
C12 C13 1.362(6) .
C12 H12 0.9300 .
C13 H13 0.9300 .
C14 H14A 0.9600 .
C14 H14B 0.9600 .
C14 H14C 0.9600 .
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
C5 N3 N4 C7 -179.2(3) . . . .
Ni1 N3 N4 C7 2.0(4) . . . .
C4 N1 C1 C2 -1.1(6) . . . .
Ni1 N1 C1 C2 179.8(3) . . . .
C3 N2 C2 C1 -0.8(7) . . . .
N1 C1 C2 N2 1.7(8) . . . .
C2 N2 C3 C4 -0.6(7) . . . .
C1 N1 C4 C3 -0.3(6) . . . .
Ni1 N1 C4 C3 179.0(3) . . . .
C1 N1 C4 C5 -179.2(3) . . . .
Ni1 N1 C4 C5 0.1(4) . . . .
N2 C3 C4 N1 1.2(6) . . . .
N2 C3 C4 C5 180.0(4) . . . .
N4 N3 C5 C4 176.4(3) . . . .
Ni1 N3 C5 C4 -4.8(5) . . . .
N4 N3 C5 C6 -2.8(6) . . . .
Ni1 N3 C5 C6 176.0(3) . . . .
N1 C4 C5 N3 2.8(5) . . . .
C3 C4 C5 N3 -176.0(4) . . . .
N1 C4 C5 C6 -178.0(4) . . . .
C3 C4 C5 C6 3.1(6) . . . .
Ni1 O1 C7 N4 6.6(5) . . . .
Ni1 O1 C7 C8 -173.0(3) . . . .
N3 N4 C7 O1 -6.0(5) . . . .
N3 N4 C7 C8 173.6(3) . . . .
O1 C7 C8 C9 158.1(4) . . . .
N4 C7 C8 C9 -21.5(5) . . . .
O1 C7 C8 C13 -20.5(6) . . . .
N4 C7 C8 C13 159.9(4) . . . .
C13 C8 C9 C10 0.1(6) . . . .
C7 C8 C9 C10 -178.6(4) . . . .
C14 O2 C10 C11 6.3(7) . . . .
C14 O2 C10 C9 -174.6(4) . . . .
C8 C9 C10 O2 -179.9(4) . . . .
C8 C9 C10 C11 -0.7(6) . . . .
O2 C10 C11 C12 180.0(4) . . . .
C9 C10 C11 C12 0.9(6) . . . .
C10 C11 C12 C13 -0.5(7) . . . .
C11 C12 C13 C8 -0.2(7) . . . .
C9 C8 C13 C12 0.4(6) . . . .
C7 C8 C13 C12 179.0(4) . . . .
