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#$Date: 2022-07-05 10:56:50 +0300 (Tue, 05 Jul 2022) $
#$Revision: 276560 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/56/8105651.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_8105651
loop_
_publ_author_name
'Wang, Li'
'Yu, Meng'
'Liu, Ling-Zhi'
'Ma, Jin-Xia'
'Dong, Wen-Kui'
_publ_section_title
;
 Crystal structure of
 bis[2-(((3-aminopropyl)imino)methyl)-4-nitro-phenolato-κ3
 N,N′,O]nickel(II), C20H24N6NiO6
;
_journal_issue                   3
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              377
_journal_page_last               378
_journal_paper_doi               10.1515/ncrs-2017-0390
_journal_volume                  234
_journal_year                    2019
_chemical_formula_moiety         'C20 H24 N6 Ni O6'
_chemical_formula_sum            'C20 H24 N6 Ni O6'
_chemical_formula_weight         503.16
_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     direct
_cell_angle_alpha                65.236(3)
_cell_angle_beta                 81.959(3)
_cell_angle_gamma                79.882(3)
_cell_formula_units_Z            1
_cell_length_a                   5.3944(6)
_cell_length_b                   10.1144(12)
_cell_length_c                   10.9297(12)
_cell_measurement_reflns_used    3161
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.60
_cell_measurement_theta_min      2.35
_cell_volume                     531.61(11)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS-1997 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173.15
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_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  0.0188
_diffrn_reflns_av_unetI/netI     0.0305
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            3509
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        25.008
_diffrn_reflns_theta_max         25.008
_diffrn_reflns_theta_min         2.237
_exptl_absorpt_coefficient_mu    0.965
_exptl_crystal_density_diffrn    1.572
_exptl_crystal_description
;
;
_exptl_crystal_F_000             262
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.360
_refine_diff_density_min         -0.294
_refine_diff_density_rms         0.050
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     151
_refine_ls_number_reflns         1852
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.089
_refine_ls_R_factor_all          0.0285
_refine_ls_R_factor_gt           0.0262
_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)+(0.0226P)²+0.3514P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0636
_refine_ls_wR_factor_ref         0.0649
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1754
_reflns_number_total             1852
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_ncrs-2017-0390_suppl.cif
_cod_data_source_block           2
_cod_database_code               8105651
_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_max   0.861
_shelx_estimated_absorpt_t_min   0.816
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C9(H9A,H9B), C10(H10A,H10B), N3(H3A,H3B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C6(H6), C7(H7)
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-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_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
C1 C 0.3389(4) 0.1771(2) 0.54273(18) 0.0206(4) Uani 1 1 d . . . . .
C2 C 0.5111(4) 0.2699(2) 0.53549(19) 0.0235(4) Uani 1 1 d . . . . .
H2 H 0.547524 0.277142 0.614855 0.028 Uiso 1 1 calc R . . . .
C3 C 0.6259(4) 0.3497(2) 0.41251(19) 0.0240(4) Uani 1 1 d . . . . .
H3 H 0.743526 0.411483 0.408278 0.029 Uiso 1 1 calc R . . . .
C4 C 0.5753(3) 0.3435(2) 0.29081(18) 0.0177(4) Uani 1 1 d . . . . .
C5 C 0.4050(3) 0.2428(2) 0.30268(18) 0.0175(4) Uani 1 1 d . . . . .
C6 C 0.2914(4) 0.1612(2) 0.42911(19) 0.0195(4) Uani 1 1 d . . . . .
H6 H 0.180625 0.094181 0.436945 0.023 Uiso 1 1 calc R . . . .
C7 C 0.3736(3) 0.2073(2) 0.18999(18) 0.0178(4) Uani 1 1 d . . . . .
H7 H 0.312284 0.117283 0.210417 0.021 Uiso 1 1 calc R . . . .
C8 C 0.4358(3) 0.2244(2) -0.03380(19) 0.0188(4) Uani 1 1 d . . . . .
H8A H 0.331454 0.290631 -0.109262 0.023 Uiso 1 1 calc R . . . .
H8B H 0.368184 0.129066 0.009263 0.023 Uiso 1 1 calc R . . . .
C9 C 0.7105(4) 0.2017(2) -0.08818(19) 0.0195(4) Uani 1 1 d . . . . .
H9A H 0.814677 0.141730 -0.010963 0.023 Uiso 1 1 calc R . . . .
H9B H 0.719484 0.145651 -0.144655 0.023 Uiso 1 1 calc R . . . .
C10 C 0.8226(3) 0.3438(2) -0.17157(18) 0.0181(4) Uani 1 1 d . . . . .
H10A H 0.993078 0.320713 -0.210498 0.022 Uiso 1 1 calc R . . . .
H10B H 0.716016 0.405812 -0.247291 0.022 Uiso 1 1 calc R . . . .
N1 N 0.2185(3) 0.09298(18) 0.67192(16) 0.0234(4) Uani 1 1 d . . . . .
N2 N 0.4228(3) 0.28871(17) 0.06554(15) 0.0159(3) Uani 1 1 d . . . . .
N3 N 0.8408(3) 0.42723(17) -0.08960(15) 0.0184(3) Uani 1 1 d . . . . .
H3A H 0.918194 0.507404 -0.143334 0.022 Uiso 1 1 calc R . . . .
H3B H 0.943674 0.369786 -0.022393 0.022 Uiso 1 1 calc R . . . .
Ni1 Ni 0.500000 0.500000 0.000000 0.01459(12) Uani 1 2 d S T P . .
O1 O 0.0577(3) 0.01700(19) 0.67698(15) 0.0402(4) Uani 1 1 d . . . . .
O2 O 0.2793(3) 0.09820(16) 0.77417(13) 0.0284(3) Uani 1 1 d . . . . .
O3 O 0.6806(2) 0.42554(14) 0.17693(12) 0.0189(3) 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'
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
C2 C1 N1 119.18(17) . .
C6 C1 C2 121.08(17) . .
C6 C1 N1 119.69(17) . .
C1 C2 H2 120.4 . .
C3 C2 C1 119.12(18) . .
C3 C2 H2 120.4 . .
C2 C3 H3 118.8 . .
C2 C3 C4 122.41(17) . .
C4 C3 H3 118.8 . .
C3 C4 C5 116.96(16) . .
O3 C4 C3 119.90(16) . .
O3 C4 C5 123.14(16) . .
C4 C5 C7 121.88(16) . .
C6 C5 C4 119.82(17) . .
C6 C5 C7 117.73(16) . .
C1 C6 C5 120.49(17) . .
C1 C6 H6 119.8 . .
C5 C6 H6 119.8 . .
C5 C7 H7 117.7 . .
N2 C7 C5 124.62(16) . .
N2 C7 H7 117.7 . .
H8A C8 H8B 108.2 . .
C9 C8 H8A 109.7 . .
C9 C8 H8B 109.7 . .
N2 C8 H8A 109.7 . .
N2 C8 H8B 109.7 . .
N2 C8 C9 109.75(14) . .
C8 C9 H9A 108.8 . .
C8 C9 H9B 108.8 . .
H9A C9 H9B 107.7 . .
C10 C9 C8 113.97(16) . .
C10 C9 H9A 108.8 . .
C10 C9 H9B 108.8 . .
C9 C10 H10A 109.2 . .
C9 C10 H10B 109.2 . .
H10A C10 H10B 107.9 . .
N3 C10 C9 112.08(15) . .
N3 C10 H10A 109.2 . .
N3 C10 H10B 109.2 . .
O1 N1 C1 118.96(16) . .
O2 N1 C1 119.07(16) . .
O2 N1 O1 121.97(16) . .
C7 N2 C8 117.97(15) . .
C7 N2 Ni1 123.18(12) . .
C8 N2 Ni1 118.79(11) . .
C10 N3 H3A 107.9 . .
C10 N3 H3B 107.9 . .
C10 N3 Ni1 117.61(11) . .
H3A N3 H3B 107.2 . .
Ni1 N3 H3A 107.9 . .
Ni1 N3 H3B 107.9 . .
N2 Ni1 N2 180.0 2_665 .
N2 Ni1 N3 85.16(6) . .
N2 Ni1 N3 94.84(6) . 2_665
N2 Ni1 N3 85.16(6) 2_665 2_665
N2 Ni1 N3 94.84(6) 2_665 .
N2 Ni1 O3 94.13(5) 2_665 .
N2 Ni1 O3 85.87(5) . .
N2 Ni1 O3 85.87(5) 2_665 2_665
N2 Ni1 O3 94.13(5) . 2_665
N3 Ni1 N3 180.0 2_665 .
O3 Ni1 N3 87.93(6) 2_665 2_665
O3 Ni1 N3 92.07(6) . 2_665
O3 Ni1 N3 92.07(6) 2_665 .
O3 Ni1 N3 87.93(6) . .
O3 Ni1 O3 180.0 . 2_665
C4 O3 Ni1 120.62(11) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.405(3) .
C1 C6 1.380(3) .
C1 N1 1.439(2) .
C2 H2 0.9500 .
C2 C3 1.369(3) .
C3 H3 0.9500 .
C3 C4 1.423(3) .
C4 C5 1.443(3) .
C4 O3 1.290(2) .
C5 C6 1.397(3) .
C5 C7 1.458(3) .
C6 H6 0.9500 .
C7 H7 0.9500 .
C7 N2 1.279(2) .
C8 H8A 0.9900 .
C8 H8B 0.9900 .
C8 C9 1.533(3) .
C8 N2 1.470(2) .
C9 H9A 0.9900 .
C9 H9B 0.9900 .
C9 C10 1.522(3) .
C10 H10A 0.9900 .
C10 H10B 0.9900 .
C10 N3 1.487(2) .
N1 O1 1.238(2) .
N1 O2 1.232(2) .
N2 Ni1 2.0494(15) .
N3 H3A 0.9100 .
N3 H3B 0.9100 .
N3 Ni1 2.1227(15) .
Ni1 O3 2.0749(12) 2_665
Ni1 O3 2.0749(12) .
