#------------------------------------------------------------------------------
#$Date: 2016-03-23 03:39:23 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179255 $
#$URL: svn://www.crystallography.net/cod/cif/4/31/75/4317539.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_4317539
loop_
_publ_author_name
'Sergey V. Kryatov'
'B. Sharmila Mohanraj'
'Vladislav V. Tarasov'
'Olga P. Kryatova'
'Elena V. Rybak-Akimova'
'Bharathi Nuthakki'
'James F. Rusling'
'Richard J. Staples'
'Alexander Y. Nazarenko'
_publ_section_title
;
 Nickel(II) Complexes with Tetra- and Pentadentate Aminopyridine Ligands:
 Synthesis, Structure, Electrochemistry, and Reduction to Nickel(I)
 Species
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              923
_journal_page_last               930
_journal_paper_doi               10.1021/ic010397n
_journal_volume                  41
_journal_year                    2002
_chemical_formula_sum            'C18 H26 Cl2 N4 Ni O8'
_chemical_formula_weight         556.04
_chemical_name_systematic
; 
  ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 97.508(9)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   15.599(6)
_cell_length_b                   9.111(4)
_cell_length_c                   16.219(6)
_cell_measurement_temperature    293(2)
_cell_volume                     2285.3(16)
_computing_cell_refinement       'SMART (BRUKER, V5.054, 1998)'
_computing_data_collection       'ASTRO (BRUKER, V5.007, 1997)'
_computing_data_reduction        'SAINT (BRUKER, V6.01, 1999)'
_computing_molecular_graphics    'SHELXTL (BRUKER, 1998, V5.1)'
_computing_publication_material  'XCIF (Sheldrick and BRUKER, 1997, V5.1)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_method       'ω, 0.3 deg'
_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  0.0492
_diffrn_reflns_av_sigmaI/netI    0.0524
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            16544
_diffrn_reflns_theta_full        28.37
_diffrn_reflns_theta_max         28.37
_diffrn_reflns_theta_min         1.32
_diffrn_standards_decay_%        <1
_diffrn_standards_interval_count 0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.135
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.616
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1152
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.767
_refine_diff_density_min         -0.403
_refine_diff_density_rms         0.071
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     325
_refine_ls_number_reflns         5694
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.099
_refine_ls_R_factor_all          0.0673
_refine_ls_R_factor_gt           0.0458
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0491P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1111
_refine_ls_wR_factor_ref         0.1174
_reflns_number_gt                3877
_reflns_number_total             5694
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic010397n_2.cif
_cod_data_source_block           era8
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to the built-in table from CIF Core dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 
;
_cod_original_cell_volume        2285.5(15)
_cod_database_code               4317539
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Ni1 Ni 0.25136(2) 0.34211(3) 0.55781(2) 0.03673(12) Uani 1 1 d . . .
N1 N 0.19799(14) 0.4857(2) 0.48399(13) 0.0398(5) Uani 1 1 d . . .
N2 N 0.30171(16) 0.1909(3) 0.63426(15) 0.0492(6) Uani 1 1 d . . .
N3 N 0.17325(16) 0.3870(3) 0.63704(15) 0.0516(6) Uani 1 1 d . . .
N4 N 0.33528(15) 0.3018(2) 0.48525(13) 0.0403(5) Uani 1 1 d . . .
C1 C 0.18679(18) 0.6220(3) 0.51143(19) 0.0454(7) Uani 1 1 d . . .
C2 C 0.1497(2) 0.7292(3) 0.4573(2) 0.0553(8) Uani 1 1 d . . .
H2A H 0.1424 0.8240 0.4764 0.066 Uiso 1 1 calc R . .
C3 C 0.1241(2) 0.6948(4) 0.3760(2) 0.0600(9) Uani 1 1 d . . .
H3A H 0.1003 0.7666 0.3391 0.072 Uiso 1 1 calc R . .
C4 C 0.1335(2) 0.5542(4) 0.34872(19) 0.0568(8) Uani 1 1 d . . .
H4A H 0.1151 0.5287 0.2937 0.068 Uiso 1 1 calc R . .
C5 C 0.17096(18) 0.4511(3) 0.40450(17) 0.0481(7) Uani 1 1 d . . .
H5A H 0.1776 0.3553 0.3865 0.058 Uiso 1 1 calc R . .
C6 C 0.2117(2) 0.6455(3) 0.6030(2) 0.0665(10) Uani 1 1 d . . .
H6A H 0.2013 0.7471 0.6167 0.080 Uiso 1 1 calc R . .
H6B H 0.2728 0.6255 0.6176 0.080 Uiso 1 1 calc R . .
C7 C 0.1599(3) 0.5459(4) 0.6524(2) 0.0732(11) Uani 1 1 d . . .
H7A H 0.1757 0.5659 0.7112 0.088 Uiso 1 1 calc R . .
H7B H 0.0989 0.5687 0.6385 0.088 Uiso 1 1 calc R . .
C8 C 0.2112(3) 0.3184(5) 0.7173(2) 0.0795(12) Uani 1 1 d . . .
H8A H 0.2578 0.3790 0.7443 0.095 Uiso 1 1 calc R . .
H8B H 0.1674 0.3092 0.7543 0.095 Uiso 1 1 calc R . .
C9 C 0.2445(3) 0.1726(4) 0.6989(2) 0.0758(11) Uani 1 1 d . . .
H9A H 0.1970 0.1075 0.6793 0.091 Uiso 1 1 calc R . .
H9B H 0.2763 0.1305 0.7487 0.091 Uiso 1 1 calc R . .
C10 C 0.3154(3) 0.0455(4) 0.5952(2) 0.0940(15) Uani 1 1 d . . .
H10A H 0.2766 -0.0258 0.6150 0.113 Uiso 1 1 calc R . .
H10B H 0.3741 0.0133 0.6131 0.113 Uiso 1 1 calc R . .
C11 C 0.3004(3) 0.0481(3) 0.5013(2) 0.0705(10) Uani 1 1 d . . .
H11A H 0.3143 -0.0474 0.4802 0.085 Uiso 1 1 calc R . .
H11B H 0.2397 0.0673 0.4829 0.085 Uiso 1 1 calc R . .
C12 C 0.38110(19) 0.4112(3) 0.45625(17) 0.0475(7) Uani 1 1 d . . .
H12A H 0.3674 0.5078 0.4677 0.057 Uiso 1 1 calc R . .
C17 C 0.3539(2) 0.1622(3) 0.46656(18) 0.0486(7) Uani 1 1 d . . .
C18 C 0.4472(2) 0.3851(4) 0.41045(19) 0.0585(8) Uani 1 1 d . . .
H18A H 0.4777 0.4629 0.3913 0.070 Uiso 1 1 calc R . .
C19 C 0.4678(2) 0.2443(4) 0.3931(2) 0.0668(9) Uani 1 1 d . . .
H19A H 0.5135 0.2245 0.3632 0.080 Uiso 1 1 calc R . .
C20 C 0.4198(2) 0.1317(4) 0.4207(2) 0.0641(9) Uani 1 1 d . . .
H20A H 0.4320 0.0349 0.4082 0.077 Uiso 1 1 calc R . .
C21 C 0.3873(2) 0.2468(5) 0.6729(2) 0.0838(13) Uani 1 1 d . . .
H21A H 0.4144 0.1750 0.7111 0.126 Uiso 1 1 calc R . .
H21B H 0.3794 0.3363 0.7022 0.126 Uiso 1 1 calc R . .
H21C H 0.4233 0.2650 0.6303 0.126 Uiso 1 1 calc R . .
C22 C 0.0888(2) 0.3188(5) 0.6064(3) 0.0949(14) Uani 1 1 d . . .
H22A H 0.0483 0.3394 0.6446 0.142 Uiso 1 1 calc R . .
H22B H 0.0959 0.2146 0.6020 0.142 Uiso 1 1 calc R . .
H22C H 0.0676 0.3583 0.5527 0.142 Uiso 1 1 calc R . .
Cl1 Cl 0.37233(6) 0.74167(11) 0.80087(5) 0.0650(2) Uani 1 1 d . . .
O1 O 0.4101(2) 0.7463(3) 0.88447(15) 0.0873(9) Uani 1 1 d . A .
O2 O 0.4243(4) 0.8651(7) 0.7651(4) 0.0721(16) Uani 0.50 1 d P A 1
O2A O 0.3513(12) 0.8596(10) 0.7662(7) 0.199(7) Uani 0.50 1 d P A 2
O3 O 0.2879(4) 0.7973(12) 0.7790(5) 0.113(3) Uani 0.50 1 d P A 1
O3A O 0.2947(4) 0.6456(10) 0.8132(5) 0.118(2) Uani 0.50 1 d P A 2
O4 O 0.4010(2) 0.6250(3) 0.7576(2) 0.1120(12) Uani 1 1 d . A .
Cl2 Cl 0.01727(5) 0.12172(9) 0.36847(5) 0.0554(2) Uani 1 1 d . . .
O5 O 0.0142(2) 0.2289(4) 0.3078(2) 0.1207(12) Uani 1 1 d . B .
O6 O 0.0946(3) 0.0919(6) 0.4119(4) 0.199(3) Uani 1 1 d . B .
O7 O 0.0315(6) 0.0049(7) 0.3129(4) 0.129(3) Uani 0.50 1 d P B 1
O7A O 0.0030(5) 0.2211(9) 0.4319(4) 0.127(3) Uani 0.50 1 d P B 2
O8 O -0.0578(3) 0.0523(6) 0.3748(3) 0.197(2) Uani 1 1 d . B 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'
Cl Cl 0.1484 0.1585 '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
N1 Ni1 N4 91.35(10) . . ?
N1 Ni1 N3 90.63(10) . . ?
N4 Ni1 N3 175.92(10) . . ?
N1 Ni1 N2 177.67(10) . . ?
N4 Ni1 N2 90.25(10) . . ?
N3 Ni1 N2 87.89(11) . . ?
C1 N1 C5 120.0(2) . . ?
C1 N1 Ni1 119.80(18) . . ?
C5 N1 Ni1 120.21(19) . . ?
C9 N2 C21 109.4(3) . . ?
C9 N2 C10 109.6(3) . . ?
C21 N2 C10 108.1(3) . . ?
C9 N2 Ni1 107.5(2) . . ?
C21 N2 Ni1 106.9(2) . . ?
C10 N2 Ni1 115.1(2) . . ?
C22 N3 C7 109.0(3) . . ?
C22 N3 C8 110.5(3) . . ?
C7 N3 C8 108.0(3) . . ?
C22 N3 Ni1 107.4(2) . . ?
C7 N3 Ni1 115.6(2) . . ?
C8 N3 Ni1 106.17(19) . . ?
C12 N4 C17 118.7(3) . . ?
C12 N4 Ni1 120.74(19) . . ?
C17 N4 Ni1 120.4(2) . . ?
N1 C1 C2 120.3(3) . . ?
N1 C1 C6 115.7(2) . . ?
C2 C1 C6 123.9(3) . . ?
C3 C2 C1 119.7(3) . . ?
C2 C3 C4 119.8(3) . . ?
C3 C4 C5 118.7(3) . . ?
N1 C5 C4 121.6(3) . . ?
C1 C6 C7 110.6(3) . . ?
N3 C7 C6 113.5(3) . . ?
C9 C8 N3 108.1(3) . . ?
C8 C9 N2 107.8(3) . . ?
N2 C10 C11 113.7(3) . . ?
C17 C11 C10 111.8(3) . . ?
N4 C12 C18 122.2(3) . . ?
N4 C17 C20 120.7(3) . . ?
N4 C17 C11 115.2(3) . . ?
C20 C17 C11 124.0(3) . . ?
C19 C18 C12 119.5(3) . . ?
C18 C19 C20 118.7(3) . . ?
C17 C20 C19 120.1(3) . . ?
O2A Cl1 O4 121.5(7) . . ?
O2A Cl1 O1 117.7(5) . . ?
O4 Cl1 O1 112.98(19) . . ?
O2A Cl1 O3 52.5(8) . . ?
O4 Cl1 O3 120.1(4) . . ?
O1 Cl1 O3 119.4(4) . . ?
O2A Cl1 O3A 112.9(9) . . ?
O4 Cl1 O3A 86.6(4) . . ?
O1 Cl1 O3A 97.5(3) . . ?
O3 Cl1 O3A 60.7(4) . . ?
O2A Cl1 O2 47.0(9) . . ?
O4 Cl1 O2 98.6(3) . . ?
O1 Cl1 O2 99.5(3) . . ?
O3 Cl1 O2 99.4(5) . . ?
O3A Cl1 O2 158.6(4) . . ?
O6 Cl2 O8 126.6(3) . . ?
O6 Cl2 O5 117.4(3) . . ?
O8 Cl2 O5 115.9(2) . . ?
O6 Cl2 O7A 87.9(4) . . ?
O8 Cl2 O7A 91.4(4) . . ?
O5 Cl2 O7A 94.1(4) . . ?
O6 Cl2 O7 88.7(4) . . ?
O8 Cl2 O7 84.7(4) . . ?
O5 Cl2 O7 94.0(4) . . ?
O7A Cl2 O7 171.8(5) . . ?
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 N1 1.892(2) . ?
Ni1 N4 1.907(2) . ?
Ni1 N3 1.927(3) . ?
Ni1 N2 1.949(2) . ?
N1 C1 1.339(3) . ?
N1 C5 1.341(3) . ?
N2 C9 1.473(4) . ?
N2 C21 1.489(4) . ?
N2 C10 1.496(4) . ?
N3 C22 1.482(4) . ?
N3 C7 1.489(4) . ?
N3 C8 1.495(4) . ?
N4 C12 1.347(4) . ?
N4 C17 1.348(3) . ?
C1 C2 1.388(4) . ?
C1 C6 1.500(4) . ?
C2 C3 1.363(5) . ?
C3 C4 1.370(5) . ?
C4 C5 1.380(4) . ?
C6 C7 1.513(5) . ?
C8 C9 1.470(5) . ?
C10 C11 1.510(5) . ?
C11 C17 1.489(5) . ?
C12 C18 1.368(4) . ?
C17 C20 1.374(5) . ?
C18 C19 1.361(5) . ?
C19 C20 1.380(5) . ?
Cl1 O2A 1.237(7) . ?
Cl1 O4 1.380(3) . ?
Cl1 O1 1.407(2) . ?
Cl1 O3 1.412(7) . ?
Cl1 O3A 1.528(7) . ?
Cl1 O2 1.544(6) . ?
Cl2 O6 1.343(4) . ?
Cl2 O8 1.347(4) . ?
Cl2 O5 1.383(3) . ?
Cl2 O7A 1.409(6) . ?
Cl2 O7 1.431(6) . ?
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
N4 Ni1 N1 C1 -125.4(2) . . . . ?
N3 Ni1 N1 C1 51.0(2) . . . . ?
N2 Ni1 N1 C1 102(2) . . . . ?
N4 Ni1 N1 C5 55.0(2) . . . . ?
N3 Ni1 N1 C5 -128.6(2) . . . . ?
N2 Ni1 N1 C5 -78(3) . . . . ?
N1 Ni1 N2 C9 -39(3) . . . . ?
N4 Ni1 N2 C9 -172.5(2) . . . . ?
N3 Ni1 N2 C9 11.2(2) . . . . ?
N1 Ni1 N2 C21 -157(2) . . . . ?
N4 Ni1 N2 C21 70.1(2) . . . . ?
N3 Ni1 N2 C21 -106.3(2) . . . . ?
N1 Ni1 N2 C10 83(3) . . . . ?
N4 Ni1 N2 C10 -50.0(3) . . . . ?
N3 Ni1 N2 C10 133.6(3) . . . . ?
N1 Ni1 N3 C22 76.4(3) . . . . ?
N4 Ni1 N3 C22 -164.6(13) . . . . ?
N2 Ni1 N3 C22 -101.8(3) . . . . ?
N1 Ni1 N3 C7 -45.5(2) . . . . ?
N4 Ni1 N3 C7 73.4(14) . . . . ?
N2 Ni1 N3 C7 136.3(2) . . . . ?
N1 Ni1 N3 C8 -165.3(2) . . . . ?
N4 Ni1 N3 C8 -46.4(15) . . . . ?
N2 Ni1 N3 C8 16.5(2) . . . . ?
N1 Ni1 N4 C12 51.5(2) . . . . ?
N3 Ni1 N4 C12 -67.5(14) . . . . ?
N2 Ni1 N4 C12 -130.2(2) . . . . ?
N1 Ni1 N4 C17 -133.0(2) . . . . ?
N3 Ni1 N4 C17 108.0(14) . . . . ?
N2 Ni1 N4 C17 45.3(2) . . . . ?
C5 N1 C1 C2 -2.0(4) . . . . ?
Ni1 N1 C1 C2 178.4(2) . . . . ?
C5 N1 C1 C6 174.5(3) . . . . ?
Ni1 N1 C1 C6 -5.1(4) . . . . ?
N1 C1 C2 C3 0.5(5) . . . . ?
C6 C1 C2 C3 -175.7(3) . . . . ?
C1 C2 C3 C4 1.3(5) . . . . ?
C2 C3 C4 C5 -1.5(5) . . . . ?
C1 N1 C5 C4 1.8(4) . . . . ?
Ni1 N1 C5 C4 -178.6(2) . . . . ?
C3 C4 C5 N1 -0.1(5) . . . . ?
N1 C1 C6 C7 -59.3(4) . . . . ?
C2 C1 C6 C7 117.1(3) . . . . ?
C22 N3 C7 C6 -121.8(3) . . . . ?
C8 N3 C7 C6 118.1(3) . . . . ?
Ni1 N3 C7 C6 -0.7(4) . . . . ?
C1 C6 C7 N3 60.6(4) . . . . ?
C22 N3 C8 C9 74.7(4) . . . . ?
C7 N3 C8 C9 -166.1(3) . . . . ?
Ni1 N3 C8 C9 -41.4(3) . . . . ?
N3 C8 C9 N2 52.3(4) . . . . ?
C21 N2 C9 C8 78.8(4) . . . . ?
C10 N2 C9 C8 -162.8(3) . . . . ?
Ni1 N2 C9 C8 -37.0(4) . . . . ?
C9 N2 C10 C11 130.1(4) . . . . ?
C21 N2 C10 C11 -110.6(4) . . . . ?
Ni1 N2 C10 C11 8.8(5) . . . . ?
N2 C10 C11 C17 54.9(5) . . . . ?
C17 N4 C12 C18 -1.8(4) . . . . ?
Ni1 N4 C12 C18 173.8(2) . . . . ?
C12 N4 C17 C20 1.7(4) . . . . ?
Ni1 N4 C17 C20 -173.9(2) . . . . ?
C12 N4 C17 C11 179.8(3) . . . . ?
Ni1 N4 C17 C11 4.2(3) . . . . ?
C10 C11 C17 N4 -64.6(4) . . . . ?
C10 C11 C17 C20 113.5(4) . . . . ?
N4 C12 C18 C19 0.1(4) . . . . ?
C12 C18 C19 C20 1.6(5) . . . . ?
N4 C17 C20 C19 0.0(5) . . . . ?
C11 C17 C20 C19 -178.0(3) . . . . ?
C18 C19 C20 C17 -1.6(5) . . . . ?
