#------------------------------------------------------------------------------
#$Date: 2025-08-19 15:18:28 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301805 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/73/2227384.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_2227384
loop_
_publ_author_name
'Kim, Jin Hoon'
'Kim, Du-Hyun'
'Kim, Pan-Gi'
'Kim, Cheal'
'Kim, Youngmee'
_publ_section_title
;
 Bis(di-2-pyridylmethanediol-κ³N,O,N')nickel(II)
 dibenzoate
;
_journal_coeditor_code           DN2601
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m1281
_journal_page_last               m1282
_journal_paper_doi               10.1107/S160053681003669X
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          '[Ni (C11 H10 N2 O2)2] (C7 H5 O2)2'
_chemical_formula_moiety         'C22 H20 N4 Ni O4 2+, 2(C7 H5 O2 -)'
_chemical_formula_sum            'C36 H30 N4 Ni O8'
_chemical_formula_weight         705.35
_chemical_name_systematic
;
Bis(di-2-pyridylmethanediol-κ³N,O,N')nickel(II)
dibenzoate
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXTL
_cell_angle_alpha                90.00
_cell_angle_beta                 123.526(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   24.065(8)
_cell_length_b                   8.681(3)
_cell_length_c                   17.718(6)
_cell_measurement_reflns_used    526
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      18.75
_cell_measurement_theta_min      2.56
_cell_volume                     3085.6(18)
_computing_cell_refinement       'SAINT (Bruker, 1997)'
_computing_data_collection       'SMART (Bruker, 1997)'
_computing_data_reduction        'SAINT (Bruker, 1997)'
_computing_molecular_graphics
'ORTEPIII (Burnett & Johnson, 1996) and ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker SMART CCD'
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0947
_diffrn_reflns_av_sigmaI/netI    0.1328
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            8329
_diffrn_reflns_theta_full        25.99
_diffrn_reflns_theta_max         25.99
_diffrn_reflns_theta_min         2.03
_exptl_absorpt_coefficient_mu    0.692
_exptl_absorpt_correction_T_max  0.966
_exptl_absorpt_correction_T_min  0.959
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 1997)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.518
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1464
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.376
_refine_diff_density_min         -0.335
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     222
_refine_ls_number_reflns         3031
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.009
_refine_ls_R_factor_all          0.1156
_refine_ls_R_factor_gt           0.0574
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0938
_refine_ls_wR_factor_ref         0.1088
_reflns_number_gt                1818
_reflns_number_total             3031
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            dn2601.cif
_cod_data_source_block           I
_cod_original_cell_volume        3085.7(17)
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2227384
_cod_database_fobs_code          2227384
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Ni Ni1 0.5000 0.54475(8) 0.7500 0.0218(2) Uani d S 1 . .
O O1 0.42807(11) 0.6969(3) 0.74041(15) 0.0272(6) Uani d . 1 . .
H H1O 0.4294 0.7180 0.7877 0.041 Uiso d R 1 . .
O O2 0.31141(11) 0.6882(3) 0.65747(15) 0.0311(7) Uani d . 1 . .
H H2O 0.3095 0.6916 0.7034 0.047 Uiso d R 1 . .
N N1 0.43794(14) 0.3935(4) 0.75897(18) 0.0240(8) Uani d . 1 . .
N N2 0.43061(13) 0.5602(3) 0.61309(17) 0.0224(7) Uani d . 1 . .
C C1 0.45080(19) 0.2545(5) 0.7972(2) 0.0295(10) Uani d . 1 . .
H H1 0.4945 0.2135 0.8250 0.035 Uiso calc R 1 . .
C C2 0.4030(2) 0.1682(5) 0.7979(2) 0.0340(10) Uani d . 1 . .
H H2 0.4136 0.0696 0.8257 0.041 Uiso calc R 1 . .
C C3 0.33914(19) 0.2273(5) 0.7573(2) 0.0336(10) Uani d . 1 . .
H H3 0.3053 0.1696 0.7564 0.040 Uiso calc R 1 . .
C C4 0.32564(18) 0.3714(5) 0.7182(2) 0.0282(10) Uani d . 1 . .
H H4 0.2823 0.4147 0.6904 0.034 Uiso calc R 1 . .
C C5 0.37576(16) 0.4519(5) 0.7200(2) 0.0231(9) Uani d . 1 . .
C C6 0.36850(16) 0.6119(4) 0.6785(2) 0.0244(9) Uani d . 1 . .
C C7 0.36976(17) 0.5939(4) 0.5939(2) 0.0215(9) Uani d . 1 . .
C C8 0.31530(18) 0.6127(4) 0.5068(2) 0.0278(9) Uani d . 1 . .
H H8 0.2725 0.6345 0.4949 0.033 Uiso calc R 1 . .
C C9 0.32512(19) 0.5986(4) 0.4372(2) 0.0306(10) Uani d . 1 . .
H H9 0.2886 0.6117 0.3763 0.037 Uiso calc R 1 . .
C C10 0.38729(18) 0.5658(5) 0.4555(2) 0.0326(10) Uani d . 1 . .
H H10 0.3944 0.5566 0.4081 0.039 Uiso calc R 1 . .
C C11 0.43897(17) 0.5467(5) 0.5446(2) 0.0286(9) Uani d . 1 . .
H H11 0.4821 0.5230 0.5580 0.034 Uiso calc R 1 . .
O O21 0.42695(12) 0.7889(3) 0.87550(16) 0.0364(7) Uani d . 1 . .
O O22 0.31909(12) 0.7353(3) 0.80877(16) 0.0409(8) Uani d . 1 . .
C C21 0.3730(2) 0.7889(5) 0.8723(3) 0.0306(10) Uani d . 1 . .
C C22 0.37566(18) 0.8581(5) 0.9521(2) 0.0272(9) Uani d . 1 . .
C C23 0.33218(19) 0.8072(5) 0.9755(3) 0.0329(10) Uani d . 1 . .
H H23 0.3011 0.7277 0.9411 0.039 Uiso calc R 1 . .
C C24 0.3337(2) 0.8705(5) 1.0476(3) 0.0382(11) Uani d . 1 . .
H H24 0.3041 0.8339 1.0632 0.046 Uiso calc R 1 . .
C C25 0.3776(2) 0.9862(5) 1.0971(3) 0.0396(11) Uani d . 1 . .
H H25 0.3776 1.0312 1.1459 0.047 Uiso calc R 1 . .
C C26 0.42184(18) 1.0377(5) 1.0767(3) 0.0356(10) Uani d . 1 . .
H H26 0.4527 1.1170 1.1119 0.043 Uiso calc R 1 . .
C C27 0.42110(18) 0.9730(5) 1.0042(3) 0.0342(10) Uani d . 1 . .
H H27 0.4519 1.0077 0.9903 0.041 Uiso calc R 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'
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N2 Ni1 N2 2_656 . 172.49(18) ?
N2 Ni1 N1 2_656 . 95.84(11) ?
N2 Ni1 N1 . . 88.95(11) ?
N2 Ni1 N1 2_656 2_656 88.95(11) ?
N2 Ni1 N1 . 2_656 95.84(11) ?
N1 Ni1 N1 . 2_656 100.79(17) ?
N2 Ni1 O1 2_656 2_656 76.59(10) ?
N2 Ni1 O1 . 2_656 98.62(10) ?
N1 Ni1 O1 . 2_656 172.42(10) ?
N1 Ni1 O1 2_656 2_656 78.91(11) ?
N2 Ni1 O1 2_656 . 98.62(10) ?
N2 Ni1 O1 . . 76.59(10) ?
N1 Ni1 O1 . . 78.91(11) ?
N1 Ni1 O1 2_656 . 172.42(10) ?
O1 Ni1 O1 2_656 . 102.40(14) ?
C6 O1 Ni1 . . 99.7(2) ?
C6 O1 H1O . . 110.2 ?
Ni1 O1 H1O . . 118.6 ?
C6 O2 H2O . . 109.5 ?
C1 N1 C5 . . 118.7(3) ?
C1 N1 Ni1 . . 129.9(2) ?
C5 N1 Ni1 . . 111.5(3) ?
C7 N2 C11 . . 118.6(3) ?
C7 N2 Ni1 . . 112.1(2) ?
C11 N2 Ni1 . . 129.3(2) ?
N1 C1 C2 . . 122.4(4) ?
N1 C1 H1 . . 118.8 ?
C2 C1 H1 . . 118.8 ?
C1 C2 C3 . . 119.0(4) ?
C1 C2 H2 . . 120.5 ?
C3 C2 H2 . . 120.5 ?
C4 C3 C2 . . 118.9(4) ?
C4 C3 H3 . . 120.6 ?
C2 C3 H3 . . 120.6 ?
C3 C4 C5 . . 119.2(4) ?
C3 C4 H4 . . 120.4 ?
C5 C4 H4 . . 120.4 ?
N1 C5 C4 . . 121.9(4) ?
N1 C5 C6 . . 112.7(3) ?
C4 C5 C6 . . 125.5(3) ?
O2 C6 O1 . . 112.6(3) ?
O2 C6 C7 . . 110.0(3) ?
O1 C6 C7 . . 104.5(3) ?
O2 C6 C5 . . 113.4(3) ?
O1 C6 C5 . . 107.3(3) ?
C7 C6 C5 . . 108.6(3) ?
N2 C7 C8 . . 122.8(3) ?
N2 C7 C6 . . 112.6(3) ?
C8 C7 C6 . . 124.5(3) ?
C7 C8 C9 . . 117.6(4) ?
C7 C8 H8 . . 121.2 ?
C9 C8 H8 . . 121.2 ?
C10 C9 C8 . . 120.5(3) ?
C10 C9 H9 . . 119.7 ?
C8 C9 H9 . . 119.7 ?
C9 C10 C11 . . 118.1(3) ?
C9 C10 H10 . . 120.9 ?
C11 C10 H10 . . 120.9 ?
N2 C11 C10 . . 122.3(3) ?
N2 C11 H11 . . 118.8 ?
C10 C11 H11 . . 118.8 ?
O22 C21 O21 . . 124.8(4) ?
O22 C21 C22 . . 118.6(3) ?
O21 C21 C22 . . 116.6(3) ?
C27 C22 C23 . . 118.4(4) ?
C27 C22 C21 . . 121.3(3) ?
C23 C22 C21 . . 120.2(4) ?
C24 C23 C22 . . 120.7(4) ?
C24 C23 H23 . . 119.6 ?
C22 C23 H23 . . 119.6 ?
C25 C24 C23 . . 120.2(4) ?
C25 C24 H24 . . 119.9 ?
C23 C24 H24 . . 119.9 ?
C24 C25 C26 . . 120.6(4) ?
C24 C25 H25 . . 119.7 ?
C26 C25 H25 . . 119.7 ?
C25 C26 C27 . . 119.6(4) ?
C25 C26 H26 . . 120.2 ?
C27 C26 H26 . . 120.2 ?
C22 C27 C26 . . 120.4(4) ?
C22 C27 H27 . . 119.8 ?
C26 C27 H27 . . 119.8 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Ni1 N2 2_656 2.053(3) ?
Ni1 N2 . 2.053(3) ?
Ni1 N1 . 2.060(3) ?
Ni1 N1 2_656 2.060(3) ?
Ni1 O1 2_656 2.109(3) ?
Ni1 O1 . 2.109(2) ?
O1 C6 . 1.437(4) ?
O1 H1O . 0.8408 ?
O2 C6 . 1.378(4) ?
O2 H2O . 0.8405 ?
N1 C1 . 1.334(4) ?
N1 C5 . 1.353(4) ?
N2 C7 . 1.340(4) ?
N2 C11 . 1.340(4) ?
C1 C2 . 1.379(5) ?
C1 H1 . 0.9500 ?
C2 C3 . 1.385(5) ?
C2 H2 . 0.9500 ?
C3 C4 . 1.379(5) ?
C3 H3 . 0.9500 ?
C4 C5 . 1.379(5) ?
C4 H4 . 0.9500 ?
C5 C6 . 1.535(5) ?
C6 C7 . 1.525(5) ?
C7 C8 . 1.374(5) ?
C8 C9 . 1.383(5) ?
C8 H8 . 0.9500 ?
C9 C10 . 1.374(5) ?
C9 H9 . 0.9500 ?
C10 C11 . 1.377(5) ?
C10 H10 . 0.9500 ?
C11 H11 . 0.9500 ?
O21 C21 . 1.267(4) ?
O22 C21 . 1.247(4) ?
C21 C22 . 1.506(5) ?
C22 C27 . 1.388(5) ?
C22 C23 . 1.393(5) ?
C23 C24 . 1.373(5) ?
C23 H23 . 0.9500 ?
C24 C25 . 1.368(5) ?
C24 H24 . 0.9500 ?
C25 C26 . 1.373(5) ?
C25 H25 . 0.9500 ?
C26 C27 . 1.393(5) ?
C26 H26 . 0.9500 ?
C27 H27 . 0.9500 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
O1 H1O O21 . 0.84 1.70 2.537(3) 170.7
O2 H2O O22 . 0.84 1.79 2.615(4) 166.5
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139079602
