#------------------------------------------------------------------------------
#$Date: 2017-05-04 22:54:52 +0300 (Thu, 04 May 2017) $
#$Revision: 196053 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/08/73/4087322.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_4087322
loop_
_publ_author_name
'Paul, Ursula S. D.'
'Radius, Udo'
_publ_section_title
;
 Synthesis and Reactivity of Cyclic (Alkyl)(Amino)Carbene Stabilized
 Nickel Carbonyl Complexes
;
_journal_issue                   7
_journal_name_full               Organometallics
_journal_page_first              1398
_journal_paper_doi               10.1021/acs.organomet.7b00109
_journal_volume                  36
_journal_year                    2017
_chemical_formula_moiety         'C47 H70 N2 Ni O, 2(C7 H8)'
_chemical_formula_sum            'C61 H86 N2 Ni O'
_chemical_formula_weight         922.02
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/6
_cell_angle_alpha                90
_cell_angle_beta                 112.737(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   21.2791(19)
_cell_length_b                   10.7542(10)
_cell_length_c                   24.220(3)
_cell_measurement_reflns_used    9949
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      21.23
_cell_measurement_theta_min      2.18
_cell_volume                     5111.8(9)
_computing_cell_refinement       'Saint-NT v. 7.23'
_computing_data_collection       'APEX2 ver. 2014.1 (Bruker AXS)'
_computing_data_reduction        'Saint-NT v. 7.23'
_computing_molecular_graphics    'XP ver. 5.1 (Bruker AXS, 1998)'
_computing_publication_material  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker X8-APEX II'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  helios
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0363
_diffrn_reflns_av_unetI/netI     0.0245
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            30143
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         26.272
_diffrn_reflns_theta_min         1.823
_exptl_absorpt_coefficient_mu    0.422
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_correction_T_min  0.6201
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   'Sadabs 2014/3 (Bruker 2014)'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.198
_exptl_crystal_description       block
_exptl_crystal_F_000             2008
_exptl_crystal_size_max          0.362
_exptl_crystal_size_mid          0.260
_exptl_crystal_size_min          0.166
_refine_diff_density_max         0.955
_refine_diff_density_min         -0.332
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     302
_refine_ls_number_reflns         5171
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0390
_refine_ls_R_factor_gt           0.0336
_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)+(0.0429P)²+6.3511P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0856
_refine_ls_wR_factor_ref         0.0896
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4644
_reflns_number_total             5171
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            om7b00109_si_002.cif
_cod_data_source_block           compound_4b
_cod_database_code               4087322
_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   0.862
_shelx_estimated_absorpt_t_max   0.933
_shelxl_version_number           2014/6
loop_
_space_group_symop_operation_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_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
Ni1 Ni 0.5000 0.39992(2) 0.7500 0.01242(9) Uani 1 2 d S T P
O1 O 0.5000 0.13248(16) 0.7500 0.0318(4) Uani 1 2 d S T P
C1 C 0.5000 0.2393(2) 0.7500 0.0187(4) Uani 1 2 d S T P
C1_1 C 0.53309(7) 0.46090(13) 0.82856(6) 0.0128(3) Uani 1 1 d . . .
N1_1 N 0.59608(6) 0.48317(11) 0.86823(5) 0.0127(2) Uani 1 1 d . . .
C2_1 C 0.60389(7) 0.48895(15) 0.93302(6) 0.0169(3) Uani 1 1 d . . .
C3_1 C 0.53091(7) 0.51873(14) 0.92481(6) 0.0159(3) Uani 1 1 d . . .
H3A_1 H 0.5250 0.6095 0.9278 0.019 Uiso 1 1 calc R U .
H3B_1 H 0.5191 0.4766 0.9559 0.019 Uiso 1 1 calc R U .
C4_1 C 0.48526(7) 0.47124(13) 0.86210(6) 0.0132(3) Uani 1 1 d . . .
C5_1 C 0.62597(8) 0.36269(17) 0.96244(7) 0.0242(4) Uani 1 1 d . . .
H5A_1 H 0.5948 0.2985 0.9382 0.036 Uiso 1 1 calc R U .
H5B_1 H 0.6250 0.3637 1.0026 0.036 Uiso 1 1 calc R U .
H5C_1 H 0.6723 0.3445 0.9655 0.036 Uiso 1 1 calc R U .
C6_1 C 0.65454(8) 0.58623(17) 0.96949(7) 0.0253(4) Uani 1 1 d . . .
H6A_1 H 0.6985 0.5722 0.9663 0.038 Uiso 1 1 calc R U .
H6B_1 H 0.6602 0.5802 1.0115 0.038 Uiso 1 1 calc R U .
H6C_1 H 0.6376 0.6692 0.9542 0.038 Uiso 1 1 calc R U .
C7_1 C 0.45085(8) 0.34616(14) 0.86320(6) 0.0166(3) Uani 1 1 d . . .
H7A_1 H 0.4301 0.3132 0.8219 0.020 Uiso 1 1 calc R U .
H7B_1 H 0.4860 0.2861 0.8874 0.020 Uiso 1 1 calc R U .
C8_1 C 0.39590(8) 0.35631(15) 0.88899(7) 0.0202(3) Uani 1 1 d . . .
H8A_1 H 0.3734 0.2746 0.8859 0.024 Uiso 1 1 calc R U .
H8B_1 H 0.4174 0.3788 0.9319 0.024 Uiso 1 1 calc R U .
C9_1 C 0.34281(8) 0.45347(16) 0.85608(7) 0.0229(3) Uani 1 1 d . . .
H9A_1 H 0.3172 0.4258 0.8144 0.027 Uiso 1 1 calc R U .
H9B_1 H 0.3101 0.4626 0.8758 0.027 Uiso 1 1 calc R U .
C10_1 C 0.37610(8) 0.57772(15) 0.85567(7) 0.0206(3) Uani 1 1 d . . .
H10A_1 H 0.3977 0.6095 0.8971 0.025 Uiso 1 1 calc R U .
H10B_1 H 0.3409 0.6382 0.8320 0.025 Uiso 1 1 calc R U .
C11_1 C 0.42962(7) 0.56574(14) 0.82886(6) 0.0164(3) Uani 1 1 d . . .
H11A_1 H 0.4509 0.6480 0.8298 0.020 Uiso 1 1 calc R U .
H11B_1 H 0.4072 0.5402 0.7864 0.020 Uiso 1 1 calc R U .
C12_1 C 0.65306(7) 0.49806(14) 0.85013(6) 0.0135(3) Uani 1 1 d . . .
C13_1 C 0.68921(7) 0.39498(14) 0.84230(6) 0.0151(3) Uani 1 1 d . . .
C14_1 C 0.74306(8) 0.41671(15) 0.82454(7) 0.0197(3) Uani 1 1 d . . .
H14_1 H 0.7684 0.3480 0.8195 0.024 Uiso 1 1 calc R U .
C15_1 C 0.76069(8) 0.53488(16) 0.81409(7) 0.0221(3) Uani 1 1 d . . .
H15_1 H 0.7979 0.5474 0.8022 0.026 Uiso 1 1 calc R U .
C16_1 C 0.72405(8) 0.63463(15) 0.82101(7) 0.0204(3) Uani 1 1 d . . .
H16_1 H 0.7359 0.7161 0.8132 0.025 Uiso 1 1 calc R U .
C17_1 C 0.67005(7) 0.61899(14) 0.83919(6) 0.0167(3) Uani 1 1 d . . .
C18_1 C 0.67409(7) 0.26126(14) 0.85206(6) 0.0163(3) Uani 1 1 d . . .
H18_1 H 0.6315 0.2586 0.8603 0.020 Uiso 1 1 calc R U .
C19_1 C 0.66400(8) 0.18053(15) 0.79726(7) 0.0218(3) Uani 1 1 d . . .
H19A_1 H 0.6300 0.2192 0.7615 0.033 Uiso 1 1 calc R U .
H19B_1 H 0.6482 0.0978 0.8030 0.033 Uiso 1 1 calc R U .
H19C_1 H 0.7073 0.1730 0.7921 0.033 Uiso 1 1 calc R U .
C20_1 C 0.73262(8) 0.20555(15) 0.90572(7) 0.0206(3) Uani 1 1 d . . .
H20A_1 H 0.7202 0.1217 0.9137 0.031 Uiso 1 1 calc R U .
H20B_1 H 0.7414 0.2580 0.9410 0.031 Uiso 1 1 calc R U .
H20C_1 H 0.7737 0.2014 0.8968 0.031 Uiso 1 1 calc R U .
C21_1 C 0.63243(8) 0.73482(14) 0.84533(7) 0.0200(3) Uani 1 1 d . . .
H21_1 H 0.5990 0.7101 0.8631 0.024 Uiso 1 1 calc R U .
C22_1 C 0.68187(9) 0.82944(16) 0.88704(8) 0.0286(4) Uani 1 1 d . . .
H22A_1 H 0.7109 0.8636 0.8677 0.043 Uiso 1 1 calc R U .
H22B_1 H 0.7103 0.7884 0.9245 0.043 Uiso 1 1 calc R U .
H22C_1 H 0.6560 0.8969 0.8956 0.043 Uiso 1 1 calc R U .
C23_1 C 0.59328(9) 0.79500(16) 0.78458(8) 0.0290(4) Uani 1 1 d . . .
H23A_1 H 0.6251 0.8170 0.7658 0.043 Uiso 1 1 calc R U .
H23B_1 H 0.5704 0.8702 0.7901 0.043 Uiso 1 1 calc R U .
H23C_1 H 0.5593 0.7364 0.7589 0.043 Uiso 1 1 calc R U .
C1_2 C 0.42123(9) -0.03154(16) 0.53411(8) 0.0258(4) Uani 1 1 d . . .
C2_2 C 0.45153(9) 0.01571(16) 0.59156(8) 0.0278(4) Uani 1 1 d . . .
H2_2 H 0.4274 0.0742 0.6053 0.033 Uiso 1 1 calc R U .
C3_2 C 0.51629(10) -0.02070(17) 0.62931(8) 0.0318(4) Uani 1 1 d . . .
H3_2 H 0.5363 0.0128 0.6686 0.038 Uiso 1 1 calc R U .
C4_2 C 0.55162(10) -0.10545(17) 0.60987(9) 0.0345(4) Uani 1 1 d . . .
H4_2 H 0.5960 -0.1311 0.6356 0.041 Uiso 1 1 calc R U .
C5_2 C 0.52195(10) -0.15285(17) 0.55263(9) 0.0343(4) Uani 1 1 d . . .
H5_2 H 0.5462 -0.2111 0.5388 0.041 Uiso 1 1 calc R U .
C6_2 C 0.45770(10) -0.11638(16) 0.51551(8) 0.0300(4) Uani 1 1 d . . .
H6_2 H 0.4379 -0.1501 0.4763 0.036 Uiso 1 1 calc R U .
C7_2 C 0.35142(10) 0.0092(2) 0.49277(9) 0.0406(5) Uani 1 1 d . . .
H7A_2 H 0.3553 0.0683 0.4635 0.061 Uiso 1 1 calc R U .
H7B_2 H 0.3282 0.0493 0.5160 0.061 Uiso 1 1 calc R U .
H7C_2 H 0.3251 -0.0634 0.4718 0.061 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_3
C1 Ni1 C1_1 110.49(4) .
C1 Ni1 C1_1 110.49(4) 2_656
C1_1 Ni1 C1_1 139.02(9) 2_656
O1 C1 Ni1 180.0 .
N1_1 C1_1 C4_1 107.06(11) .
N1_1 C1_1 Ni1 132.26(11) .
C4_1 C1_1 Ni1 119.87(10) .
C1_1 N1_1 C12_1 121.81(11) .
C1_1 N1_1 C2_1 115.52(11) .
C12_1 N1_1 C2_1 122.66(11) .
N1_1 C2_1 C6_1 113.61(12) .
N1_1 C2_1 C5_1 109.83(12) .
C6_1 C2_1 C5_1 108.75(13) .
N1_1 C2_1 C3_1 100.12(11) .
C6_1 C2_1 C3_1 112.99(13) .
C5_1 C2_1 C3_1 111.35(13) .
C2_1 C3_1 C4_1 106.37(11) .
C2_1 C3_1 H3A_1 110.5 .
C4_1 C3_1 H3A_1 110.5 .
C2_1 C3_1 H3B_1 110.5 .
C4_1 C3_1 H3B_1 110.5 .
H3A_1 C3_1 H3B_1 108.6 .
C11_1 C4_1 C1_1 107.84(11) .
C11_1 C4_1 C7_1 108.25(12) .
C1_1 C4_1 C7_1 111.36(11) .
C11_1 C4_1 C3_1 111.30(12) .
C1_1 C4_1 C3_1 104.60(11) .
C7_1 C4_1 C3_1 113.36(11) .
C2_1 C5_1 H5A_1 109.5 .
C2_1 C5_1 H5B_1 109.5 .
H5A_1 C5_1 H5B_1 109.5 .
C2_1 C5_1 H5C_1 109.5 .
H5A_1 C5_1 H5C_1 109.5 .
H5B_1 C5_1 H5C_1 109.5 .
C2_1 C6_1 H6A_1 109.5 .
C2_1 C6_1 H6B_1 109.5 .
H6A_1 C6_1 H6B_1 109.5 .
C2_1 C6_1 H6C_1 109.5 .
H6A_1 C6_1 H6C_1 109.5 .
H6B_1 C6_1 H6C_1 109.5 .
C8_1 C7_1 C4_1 112.94(12) .
C8_1 C7_1 H7A_1 109.0 .
C4_1 C7_1 H7A_1 109.0 .
C8_1 C7_1 H7B_1 109.0 .
C4_1 C7_1 H7B_1 109.0 .
H7A_1 C7_1 H7B_1 107.8 .
C9_1 C8_1 C7_1 111.47(12) .
C9_1 C8_1 H8A_1 109.3 .
C7_1 C8_1 H8A_1 109.3 .
C9_1 C8_1 H8B_1 109.3 .
C7_1 C8_1 H8B_1 109.3 .
H8A_1 C8_1 H8B_1 108.0 .
C10_1 C9_1 C8_1 110.83(13) .
C10_1 C9_1 H9A_1 109.5 .
C8_1 C9_1 H9A_1 109.5 .
C10_1 C9_1 H9B_1 109.5 .
C8_1 C9_1 H9B_1 109.5 .
H9A_1 C9_1 H9B_1 108.1 .
C9_1 C10_1 C11_1 110.97(13) .
C9_1 C10_1 H10A_1 109.4 .
C11_1 C10_1 H10A_1 109.4 .
C9_1 C10_1 H10B_1 109.4 .
C11_1 C10_1 H10B_1 109.4 .
H10A_1 C10_1 H10B_1 108.0 .
C10_1 C11_1 C4_1 112.74(12) .
C10_1 C11_1 H11A_1 109.0 .
C4_1 C11_1 H11A_1 109.0 .
C10_1 C11_1 H11B_1 109.0 .
C4_1 C11_1 H11B_1 109.0 .
H11A_1 C11_1 H11B_1 107.8 .
C17_1 C12_1 C13_1 120.82(13) .
C17_1 C12_1 N1_1 117.82(13) .
C13_1 C12_1 N1_1 121.34(13) .
C14_1 C13_1 C12_1 117.99(14) .
C14_1 C13_1 C18_1 117.30(13) .
C12_1 C13_1 C18_1 124.71(13) .
C15_1 C14_1 C13_1 121.87(14) .
C15_1 C14_1 H14_1 119.1 .
C13_1 C14_1 H14_1 119.1 .
C16_1 C15_1 C14_1 119.39(14) .
C16_1 C15_1 H15_1 120.3 .
C14_1 C15_1 H15_1 120.3 .
C15_1 C16_1 C17_1 121.44(15) .
C15_1 C16_1 H16_1 119.3 .
C17_1 C16_1 H16_1 119.3 .
C16_1 C17_1 C12_1 118.48(14) .
C16_1 C17_1 C21_1 117.59(14) .
C12_1 C17_1 C21_1 123.92(13) .
C13_1 C18_1 C19_1 111.78(12) .
C13_1 C18_1 C20_1 110.62(12) .
C19_1 C18_1 C20_1 108.03(12) .
C13_1 C18_1 H18_1 108.8 .
C19_1 C18_1 H18_1 108.8 .
C20_1 C18_1 H18_1 108.8 .
C18_1 C19_1 H19A_1 109.5 .
C18_1 C19_1 H19B_1 109.5 .
H19A_1 C19_1 H19B_1 109.5 .
C18_1 C19_1 H19C_1 109.5 .
H19A_1 C19_1 H19C_1 109.5 .
H19B_1 C19_1 H19C_1 109.5 .
C18_1 C20_1 H20A_1 109.5 .
C18_1 C20_1 H20B_1 109.5 .
H20A_1 C20_1 H20B_1 109.5 .
C18_1 C20_1 H20C_1 109.5 .
H20A_1 C20_1 H20C_1 109.5 .
H20B_1 C20_1 H20C_1 109.5 .
C17_1 C21_1 C23_1 111.43(13) .
C17_1 C21_1 C22_1 110.86(13) .
C23_1 C21_1 C22_1 109.52(14) .
C17_1 C21_1 H21_1 108.3 .
C23_1 C21_1 H21_1 108.3 .
C22_1 C21_1 H21_1 108.3 .
C21_1 C22_1 H22A_1 109.5 .
C21_1 C22_1 H22B_1 109.5 .
H22A_1 C22_1 H22B_1 109.5 .
C21_1 C22_1 H22C_1 109.5 .
H22A_1 C22_1 H22C_1 109.5 .
H22B_1 C22_1 H22C_1 109.5 .
C21_1 C23_1 H23A_1 109.5 .
C21_1 C23_1 H23B_1 109.5 .
H23A_1 C23_1 H23B_1 109.5 .
C21_1 C23_1 H23C_1 109.5 .
H23A_1 C23_1 H23C_1 109.5 .
H23B_1 C23_1 H23C_1 109.5 .
C6_2 C1_2 C2_2 117.90(17) .
C6_2 C1_2 C7_2 120.76(17) .
C2_2 C1_2 C7_2 121.33(17) .
C3_2 C2_2 C1_2 121.23(17) .
C3_2 C2_2 H2_2 119.4 .
C1_2 C2_2 H2_2 119.4 .
C4_2 C3_2 C2_2 119.86(18) .
C4_2 C3_2 H3_2 120.1 .
C2_2 C3_2 H3_2 120.1 .
C3_2 C4_2 C5_2 119.37(18) .
C3_2 C4_2 H4_2 120.3 .
C5_2 C4_2 H4_2 120.3 .
C6_2 C5_2 C4_2 120.40(17) .
C6_2 C5_2 H5_2 119.8 .
C4_2 C5_2 H5_2 119.8 .
C5_2 C6_2 C1_2 121.24(17) .
C5_2 C6_2 H6_2 119.4 .
C1_2 C6_2 H6_2 119.4 .
C1_2 C7_2 H7A_2 109.5 .
C1_2 C7_2 H7B_2 109.5 .
H7A_2 C7_2 H7B_2 109.5 .
C1_2 C7_2 H7C_2 109.5 .
H7A_2 C7_2 H7C_2 109.5 .
H7B_2 C7_2 H7C_2 109.5 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Ni1 C1 1.728(2) .
Ni1 C1_1 1.8736(14) .
Ni1 C1_1 1.8737(14) 2_656
O1 C1 1.148(3) .
C1_1 N1_1 1.3348(18) .
C1_1 C4_1 1.5321(18) .
N1_1 C12_1 1.4487(17) .
N1_1 C2_1 1.5140(17) .
C2_1 C6_1 1.517(2) .
C2_1 C5_1 1.521(2) .
C2_1 C3_1 1.521(2) .
C3_1 C4_1 1.5398(19) .
C3_1 H3A_1 0.9900 .
C3_1 H3B_1 0.9900 .
C4_1 C11_1 1.532(2) .
C4_1 C7_1 1.537(2) .
C5_1 H5A_1 0.9800 .
C5_1 H5B_1 0.9800 .
C5_1 H5C_1 0.9800 .
C6_1 H6A_1 0.9800 .
C6_1 H6B_1 0.9800 .
C6_1 H6C_1 0.9800 .
C7_1 C8_1 1.528(2) .
C7_1 H7A_1 0.9900 .
C7_1 H7B_1 0.9900 .
C8_1 C9_1 1.519(2) .
C8_1 H8A_1 0.9900 .
C8_1 H8B_1 0.9900 .
C9_1 C10_1 1.514(2) .
C9_1 H9A_1 0.9900 .
C9_1 H9B_1 0.9900 .
C10_1 C11_1 1.519(2) .
C10_1 H10A_1 0.9900 .
C10_1 H10B_1 0.9900 .
C11_1 H11A_1 0.9900 .
C11_1 H11B_1 0.9900 .
C12_1 C17_1 1.402(2) .
C12_1 C13_1 1.403(2) .
C13_1 C14_1 1.391(2) .
C13_1 C18_1 1.512(2) .
C14_1 C15_1 1.376(2) .
C14_1 H14_1 0.9500 .
C15_1 C16_1 1.374(2) .
C15_1 H15_1 0.9500 .
C16_1 C17_1 1.391(2) .
C16_1 H16_1 0.9500 .
C17_1 C21_1 1.519(2) .
C18_1 C19_1 1.530(2) .
C18_1 C20_1 1.532(2) .
C18_1 H18_1 1.0000 .
C19_1 H19A_1 0.9800 .
C19_1 H19B_1 0.9800 .
C19_1 H19C_1 0.9800 .
C20_1 H20A_1 0.9800 .
C20_1 H20B_1 0.9800 .
C20_1 H20C_1 0.9800 .
C21_1 C23_1 1.526(2) .
C21_1 C22_1 1.530(2) .
C21_1 H21_1 1.0000 .
C22_1 H22A_1 0.9800 .
C22_1 H22B_1 0.9800 .
C22_1 H22C_1 0.9800 .
C23_1 H23A_1 0.9800 .
C23_1 H23B_1 0.9800 .
C23_1 H23C_1 0.9800 .
C1_2 C6_2 1.381(3) .
C1_2 C2_2 1.384(2) .
C1_2 C7_2 1.500(3) .
C2_2 C3_2 1.383(3) .
C2_2 H2_2 0.9500 .
C3_2 C4_2 1.375(3) .
C3_2 H3_2 0.9500 .
C4_2 C5_2 1.380(3) .
C4_2 H4_2 0.9500 .
C5_2 C6_2 1.371(3) .
C5_2 H5_2 0.9500 .
C6_2 H6_2 0.9500 .
C7_2 H7A_2 0.9800 .
C7_2 H7B_2 0.9800 .
C7_2 H7C_2 0.9800 .
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
C1 Ni1 C1_1 N1_1 85.37(14) .
C1_1 Ni1 C1_1 N1_1 -94.63(14) 2_656
C1 Ni1 C1_1 C4_1 -82.80(11) .
C1_1 Ni1 C1_1 C4_1 97.20(11) 2_656
C4_1 C1_1 N1_1 C12_1 -171.26(12) .
Ni1 C1_1 N1_1 C12_1 19.5(2) .
C4_1 C1_1 N1_1 C2_1 9.99(16) .
Ni1 C1_1 N1_1 C2_1 -159.29(11) .
C1_1 N1_1 C2_1 C6_1 -142.99(14) .
C12_1 N1_1 C2_1 C6_1 38.27(19) .
C1_1 N1_1 C2_1 C5_1 94.96(15) .
C12_1 N1_1 C2_1 C5_1 -83.78(16) .
C1_1 N1_1 C2_1 C3_1 -22.26(16) .
C12_1 N1_1 C2_1 C3_1 159.00(13) .
N1_1 C2_1 C3_1 C4_1 24.39(14) .
C6_1 C2_1 C3_1 C4_1 145.57(13) .
C5_1 C2_1 C3_1 C4_1 -91.70(14) .
N1_1 C1_1 C4_1 C11_1 125.36(12) .
Ni1 C1_1 C4_1 C11_1 -63.77(14) .
N1_1 C1_1 C4_1 C7_1 -116.01(13) .
Ni1 C1_1 C4_1 C7_1 54.86(14) .
N1_1 C1_1 C4_1 C3_1 6.80(15) .
Ni1 C1_1 C4_1 C3_1 177.66(10) .
C2_1 C3_1 C4_1 C11_1 -136.51(12) .
C2_1 C3_1 C4_1 C1_1 -20.32(15) .
C2_1 C3_1 C4_1 C7_1 101.19(14) .
C11_1 C4_1 C7_1 C8_1 -54.11(15) .
C1_1 C4_1 C7_1 C8_1 -172.49(12) .
C3_1 C4_1 C7_1 C8_1 69.88(16) .
C4_1 C7_1 C8_1 C9_1 55.04(17) .
C7_1 C8_1 C9_1 C10_1 -54.61(17) .
C8_1 C9_1 C10_1 C11_1 55.87(17) .
C9_1 C10_1 C11_1 C4_1 -57.81(17) .
C1_1 C4_1 C11_1 C10_1 176.17(12) .
C7_1 C4_1 C11_1 C10_1 55.56(16) .
C3_1 C4_1 C11_1 C10_1 -69.65(16) .
C1_1 N1_1 C12_1 C17_1 93.43(16) .
C2_1 N1_1 C12_1 C17_1 -87.91(16) .
C1_1 N1_1 C12_1 C13_1 -85.04(17) .
C2_1 N1_1 C12_1 C13_1 93.62(16) .
C17_1 C12_1 C13_1 C14_1 1.2(2) .
N1_1 C12_1 C13_1 C14_1 179.65(12) .
C17_1 C12_1 C13_1 C18_1 -179.07(13) .
N1_1 C12_1 C13_1 C18_1 -0.6(2) .
C12_1 C13_1 C14_1 C15_1 -0.7(2) .
C18_1 C13_1 C14_1 C15_1 179.56(14) .
C13_1 C14_1 C15_1 C16_1 -0.3(2) .
C14_1 C15_1 C16_1 C17_1 0.9(2) .
C15_1 C16_1 C17_1 C12_1 -0.4(2) .
C15_1 C16_1 C17_1 C21_1 -179.75(14) .
C13_1 C12_1 C17_1 C16_1 -0.7(2) .
N1_1 C12_1 C17_1 C16_1 -179.16(12) .
C13_1 C12_1 C17_1 C21_1 178.62(13) .
N1_1 C12_1 C17_1 C21_1 0.1(2) .
C14_1 C13_1 C18_1 C19_1 -53.83(17) .
C12_1 C13_1 C18_1 C19_1 126.46(15) .
C14_1 C13_1 C18_1 C20_1 66.60(16) .
C12_1 C13_1 C18_1 C20_1 -113.11(15) .
C16_1 C17_1 C21_1 C23_1 67.50(18) .
C12_1 C17_1 C21_1 C23_1 -111.81(16) .
C16_1 C17_1 C21_1 C22_1 -54.76(18) .
C12_1 C17_1 C21_1 C22_1 125.94(16) .
C6_2 C1_2 C2_2 C3_2 0.0(3) .
C7_2 C1_2 C2_2 C3_2 -179.09(17) .
C1_2 C2_2 C3_2 C4_2 -0.1(3) .
C2_2 C3_2 C4_2 C5_2 0.3(3) .
C3_2 C4_2 C5_2 C6_2 -0.3(3) .
C4_2 C5_2 C6_2 C1_2 0.2(3) .
C2_2 C1_2 C6_2 C5_2 -0.1(3) .
C7_2 C1_2 C6_2 C5_2 179.01(17) .
