#------------------------------------------------------------------------------
#$Date: 2025-08-21 00:01:10 +0200 (Thu 21 de Aug de 2025) $
#$Revision: 301838 $
#$URL: svn://www.crystallography.net/cod/cif/4/32/40/4324042.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_4324042
loop_
_publ_author_name
'Thomas G. Hodgkins'
'Douglas R. Powell'
_publ_contact_author
;
   Douglas R. Powell
   Department of Chemistry
   University of Wisconsin
   1101 University Ave. 
   Madison, WI  53706-1322  U.S.A.
;
_publ_contact_author_email       powell@chem.wisc.edu
_publ_contact_author_fax         '608 262 0381'
_publ_contact_author_phone       '608 263 4694'
_publ_section_title
;
 Derivatives of the Dimethylbis(2-pyridyl)borate(1-) Ion: Synthesis and
 Structure
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              2140
_journal_page_last               2148
_journal_paper_doi               10.1021/ic950775m
_journal_volume                  35
_journal_year                    1996
_chemical_formula_sum            'C24 H28 B2 N4 Ni'
_chemical_formula_weight         452.83
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL
_cell_angle_alpha                115.72(3)
_cell_angle_beta                 96.89(3)
_cell_angle_gamma                94.02(3)
_cell_formula_units_Z            1
_cell_length_a                   7.675(2)
_cell_length_b                   8.819(2)
_cell_length_c                   9.459(2)
_cell_measurement_reflns_used    26
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      12.5
_cell_measurement_theta_min      11.5
_cell_volume                     567.3(3)
_computing_structure_refinement  'SHELXL-92 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measurement_device       'Siemens P4'
_diffrn_measurement_method       'θ-2θ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0328
_diffrn_reflns_av_sigmaI/netI    0.0471
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            2832
_diffrn_reflns_theta_max         22.49
_diffrn_reflns_theta_min         2.42
_diffrn_standards_decay_%        4.83
_diffrn_standards_interval_count 50
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.873
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.326
_exptl_crystal_description       prism
_exptl_crystal_F_000             238
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.197
_refine_diff_density_min         -0.199
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   1.046
_refine_ls_goodness_of_fit_obs   1.063
_refine_ls_hydrogen_treatment    riding
_refine_ls_matrix_type           full
_refine_ls_number_parameters     144
_refine_ls_number_reflns         1416
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_restrained_S_obs      1.063
_refine_ls_R_factor_all          0.0349
_refine_ls_R_factor_obs          0.0308
_refine_ls_shift/esd_max         0.002
_refine_ls_shift/esd_mean        0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0341P)²+0.1135P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0767
_refine_ls_wR_factor_obs         0.0748
_reflns_number_observed          1314
_reflns_number_total             1416
_reflns_observed_criterion       >2sigma(I)
_cod_data_source_file            ic950775m_1.cif
_cod_data_source_block           compound_VIII
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc
w=1/[\s^2^(Fo^2^)+(0.0341P)^2^+0.1135P] where P=(Fo^2^+2Fc^2^)/3' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to
'w=1/[\s^2^(Fo^2^)+(0.0341P)^2^+0.1135P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_cell_volume        567.3(2)
_cod_database_code               4324042
loop_
_symmetry_equiv_pos_as_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_thermal_displace_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_group
Ni1 Ni 0.0000 0.0000 0.0000 0.0279(2) Uani 1 d S .
C1 C 0.2538(3) -0.1941(3) 0.0540(3) 0.0328(7) Uani 1 d . .
N2 N 0.2015(3) -0.1176(3) -0.0385(2) 0.0304(5) Uani 1 d . .
C3 C 0.2877(4) -0.1268(3) -0.1577(3) 0.0372(7) Uani 1 d . .
H3A H 0.2495(4) -0.0716(3) -0.2177(3) 0.045 Uiso 1 calc R .
C4 C 0.4297(4) -0.2147(4) -0.1935(4) 0.0450(8) Uani 1 d . .
H4A H 0.4879(4) -0.2183(4) -0.2755(4) 0.054 Uiso 1 calc R .
C5 C 0.4835(4) -0.2972(4) -0.1053(4) 0.0500(9) Uani 1 d . .
H5A H 0.5777(4) -0.3600(4) -0.1279(4) 0.060 Uiso 1 calc R .
C6 C 0.3965(4) -0.2861(4) 0.0171(4) 0.0460(8) Uani 1 d . .
H6A H 0.4338(4) -0.3415(4) 0.0771(4) 0.055 Uiso 1 calc R .
C7 C 0.1642(3) 0.0399(3) 0.2993(3) 0.0333(7) Uani 1 d . .
N8 N 0.1058(3) 0.1267(3) 0.2175(2) 0.0292(5) Uani 1 d . .
C9 C 0.1222(4) 0.2973(3) 0.2892(3) 0.0353(7) Uani 1 d . .
H9A H 0.0805(4) 0.3524(3) 0.2301(3) 0.042 Uiso 1 calc R .
C10 C 0.1971(4) 0.3931(4) 0.4449(3) 0.0445(8) Uani 1 d . .
H10A H 0.2087(4) 0.5111(4) 0.4907(3) 0.053 Uiso 1 calc R .
C11 C 0.2549(5) 0.3106(4) 0.5319(4) 0.0519(9) Uani 1 d . .
H11A H 0.3056(5) 0.3721(4) 0.6386(4) 0.062 Uiso 1 calc R .
C12 C 0.2372(4) 0.1358(4) 0.4598(3) 0.0465(8) Uani 1 d . .
H12A H 0.2748(4) 0.0802(4) 0.5195(3) 0.056 Uiso 1 calc R .
B13 B 0.1497(4) -0.1672(4) 0.2028(4) 0.0374(8) Uani 1 d . .
C14 C -0.0582(4) -0.2527(4) 0.1374(4) 0.0438(7) Uani 1 d . .
H14A H -0.1202(7) -0.2252(20) 0.2259(4) 0.061 Uiso 1 calc R .
H14B H -0.0645(4) -0.3738(4) 0.0798(19) 0.061 Uiso 1 calc R .
H14C H -0.1116(8) -0.2090(18) 0.0682(17) 0.061 Uiso 1 calc R .
C15 C 0.2424(5) -0.2469(4) 0.3138(4) 0.0565(9) Uani 1 d . .
H15A H 0.3631(9) -0.1942(20) 0.3548(21) 0.079 Uiso 1 calc R .
H15B H 0.2397(26) -0.3670(6) 0.2515(8) 0.079 Uiso 1 calc R .
H15C H 0.1794(18) -0.2267(24) 0.4006(15) 0.079 Uiso 1 calc R .
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'
B B 0.0013 0.0007 '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
N8 Ni1 N8 180.0 2 . ?
N8 Ni1 N2 90.66(9) 2 . ?
N8 Ni1 N2 89.34(9) . . ?
N8 Ni1 N2 89.34(9) 2 2 ?
N8 Ni1 N2 90.66(9) . 2 ?
N2 Ni1 N2 180.0 . 2 ?
N2 C1 C6 117.1(3) . . ?
N2 C1 B13 118.0(2) . . ?
C6 C1 B13 124.9(3) . . ?
C3 N2 C1 121.1(2) . . ?
C3 N2 Ni1 120.2(2) . . ?
C1 N2 Ni1 118.8(2) . . ?
N2 C3 C4 122.4(3) . . ?
C3 C4 C5 118.2(3) . . ?
C4 C5 C6 119.2(3) . . ?
C5 C6 C1 122.0(3) . . ?
N8 C7 C12 117.1(2) . . ?
N8 C7 B13 118.4(2) . . ?
C12 C7 B13 124.5(3) . . ?
C9 N8 C7 120.8(2) . . ?
C9 N8 Ni1 120.9(2) . . ?
C7 N8 Ni1 118.3(2) . . ?
N8 C9 C10 122.8(3) . . ?
C9 C10 C11 118.2(3) . . ?
C12 C11 C10 119.4(3) . . ?
C11 C12 C7 121.7(3) . . ?
C15 B13 C7 111.6(2) . . ?
C15 B13 C1 111.9(3) . . ?
C7 B13 C1 102.7(2) . . ?
C15 B13 C14 109.5(3) . . ?
C7 B13 C14 110.4(2) . . ?
C1 B13 C14 110.6(2) . . ?
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 N8 1.902(2) 2 ?
Ni1 N8 1.902(2) . ?
Ni1 N2 1.906(2) . ?
Ni1 N2 1.906(2) 2 ?
C1 N2 1.359(3) . ?
C1 C6 1.397(4) . ?
C1 B13 1.638(4) . ?
N2 C3 1.351(3) . ?
C3 C4 1.372(4) . ?
C4 C5 1.373(4) . ?
C5 C6 1.375(5) . ?
C7 N8 1.366(3) . ?
C7 C12 1.395(4) . ?
C7 B13 1.637(4) . ?
N8 C9 1.344(3) . ?
C9 C10 1.365(4) . ?
C10 C11 1.372(4) . ?
C11 C12 1.377(4) . ?
B13 C15 1.623(4) . ?
B13 C14 1.639(4) . ?
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
C6 C1 N2 C3 -1.8(4) . . . . ?
B13 C1 N2 C3 176.3(2) . . . . ?
C6 C1 N2 Ni1 176.9(2) . . . . ?
B13 C1 N2 Ni1 -4.9(3) . . . . ?
N8 Ni1 N2 C3 51.9(2) 2 . . . ?
N8 Ni1 N2 C3 -128.1(2) . . . . ?
N2 Ni1 N2 C3 -44.1(205) 2 . . . ?
N8 Ni1 N2 C1 -126.8(2) 2 . . . ?
N8 Ni1 N2 C1 53.2(2) . . . . ?
N2 Ni1 N2 C1 137.1(205) 2 . . . ?
C1 N2 C3 C4 0.9(4) . . . . ?
Ni1 N2 C3 C4 -177.8(2) . . . . ?
N2 C3 C4 C5 0.7(4) . . . . ?
C3 C4 C5 C6 -1.4(4) . . . . ?
C4 C5 C6 C1 0.4(5) . . . . ?
N2 C1 C6 C5 1.2(4) . . . . ?
B13 C1 C6 C5 -176.9(3) . . . . ?
C12 C7 N8 C9 1.3(4) . . . . ?
B13 C7 N8 C9 -176.9(2) . . . . ?
C12 C7 N8 Ni1 -178.4(2) . . . . ?
B13 C7 N8 Ni1 3.4(3) . . . . ?
N8 Ni1 N8 C9 140.5(19) 2 . . . ?
N2 Ni1 N8 C9 128.2(2) . . . . ?
N2 Ni1 N8 C9 -51.8(2) 2 . . . ?
N8 Ni1 N8 C7 -39.8(19) 2 . . . ?
N2 Ni1 N8 C7 -52.0(2) . . . . ?
N2 Ni1 N8 C7 128.0(2) 2 . . . ?
C7 N8 C9 C10 0.3(4) . . . . ?
Ni1 N8 C9 C10 180.0(2) . . . . ?
N8 C9 C10 C11 -1.3(4) . . . . ?
C9 C10 C11 C12 0.6(5) . . . . ?
C10 C11 C12 C7 1.0(5) . . . . ?
N8 C7 C12 C11 -1.9(4) . . . . ?
B13 C7 C12 C11 176.2(3) . . . . ?
N8 C7 B13 C15 174.4(2) . . . . ?
C12 C7 B13 C15 -3.7(4) . . . . ?
N8 C7 B13 C1 54.3(3) . . . . ?
C12 C7 B13 C1 -123.8(3) . . . . ?
N8 C7 B13 C14 -63.6(3) . . . . ?
C12 C7 B13 C14 118.4(3) . . . . ?
N2 C1 B13 C15 -173.1(2) . . . . ?
C6 C1 B13 C15 4.9(4) . . . . ?
N2 C1 B13 C7 -53.3(3) . . . . ?
C6 C1 B13 C7 124.7(3) . . . . ?
N2 C1 B13 C14 64.5(3) . . . . ?
C6 C1 B13 C14 -117.5(3) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139135271
