#------------------------------------------------------------------------------
#$Date: 2016-11-06 03:24:11 +0200 (Sun, 06 Nov 2016) $
#$Revision: 187880 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/39/4513949.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_4513949
loop_
_publ_author_name
'Lu, Zhiyao'
'Williams, Travis J.'
_publ_section_title
;
 Di(carbene)-Supported Nickel Systems for CO2Reduction Under Ambient
 Conditions
;
_journal_issue                   10
_journal_name_full               'ACS Catalysis'
_journal_page_first              6670
_journal_paper_doi               10.1021/acscatal.6b02101
_journal_volume                  6
_journal_year                    2016
_chemical_formula_moiety         'C58 H66 N8 Ni3 O4, C H2 Cl2'
_chemical_formula_sum            'C59 H68 Cl2 N8 Ni3 O4'
_chemical_formula_weight         1200.24
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_cell_angle_alpha                90
_cell_angle_beta                 109.9220(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   22.9867(14)
_cell_length_b                   8.2956(5)
_cell_length_c                   32.6131(19)
_cell_measurement_reflns_used    9862
_cell_measurement_temperature    100.(2)
_cell_measurement_theta_max      30.5168
_cell_measurement_theta_min      2.6298
_cell_volume                     5846.8(6)
_computing_cell_refinement       'APEX2 v2014.11-0 (Bruker AXS, 2014)'
_computing_data_collection
'Bruker Instrument Service v2012.12.0.3 (Bruker AXS, 2012)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS, 2013)'
_computing_publication_material  'SHELXTL XT 2014/4 (Bruker AXS, 2014)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXTL XT 2014/4 (Bruker AXS, 2014)'
_diffrn_ambient_temperature      100.(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX II CCD'
_diffrn_measurement_method       'omega- and phi-scans'
_diffrn_radiation_monochromator  'TRIUMPH curved-crystal'
_diffrn_radiation_type           'MoK\a '
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0587
_diffrn_reflns_av_unetI/netI     0.0394
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       46
_diffrn_reflns_limit_l_min       -46
_diffrn_reflns_number            141899
_diffrn_reflns_theta_full        30.54
_diffrn_reflns_theta_max         30.54
_diffrn_reflns_theta_min         1.33
_diffrn_source                   'fine-focus tube'
_exptl_absorpt_coefficient_mu    1.100
_exptl_absorpt_correction_T_max  0.87
_exptl_absorpt_correction_T_min  0.71
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2014/5 (Bruker AXS, 2014)'
_exptl_crystal_colour            'clear pale orange'
_exptl_crystal_density_diffrn    1.364
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             2512
_exptl_crystal_size_max          0.753
_exptl_crystal_size_mid          0.302
_exptl_crystal_size_min          0.126
_refine_diff_density_max         0.874
_refine_diff_density_min         -1.156
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     704
_refine_ls_number_reflns         17841
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0783
_refine_ls_R_factor_gt           0.0486
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0509P)²+10.2519P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1171
_refine_ls_wR_factor_ref         0.1316
_reflns_number_gt                12343
_reflns_number_total             17841
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            cs6b02101_si_003.cif
_cod_data_source_block           C59H68Cl2N8Ni3O4
_cod_depositor_comments
'Adding full bibliography for 4513948--4513950.cif.'
_cod_database_code               4513949
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
C C1 0.60630(11) 0.9296(3) 0.47321(8) 0.0196(5) Uani d . . . 1
H H1 0.5868 0.9609 0.4437 0.024 Uiso calc U . R 1
C C2 0.66544(11) 0.8785(3) 0.49136(8) 0.0201(5) Uani d . . . 1
H H2 0.695 0.866 0.4771 0.024 Uiso calc U . R 1
C C3 0.62050(10) 0.8777(3) 0.54313(7) 0.0120(4) Uani d . . . 1
C C4 0.73277(10) 0.7976(3) 0.56536(8) 0.0149(4) Uani d . . . 1
C C5 0.78079(11) 0.9115(3) 0.58019(8) 0.0179(5) Uani d . . . 1
C C6 0.83709(11) 0.8595(3) 0.60980(9) 0.0206(5) Uani d . . . 1
H H6 0.8699 0.9348 0.6206 0.025 Uiso calc U . R 1
C C7 0.84652(11) 0.7002(3) 0.62406(9) 0.0222(5) Uani d . . . 1
C C8 0.79899(12) 0.5906(3) 0.60725(9) 0.0214(5) Uani d . . . 1
H H8 0.8056 0.481 0.616 0.026 Uiso calc U . R 1
C C9 0.74146(11) 0.6365(3) 0.57769(8) 0.0182(5) Uani d . . . 1
C C10 0.77122(13) 1.0831(3) 0.56472(10) 0.0275(6) Uani d . . . 1
H H10A 0.8051 1.1499 0.5834 0.041 Uiso calc U . R 1
H H10B 0.7317 1.1226 0.5661 0.041 Uiso calc U . R 1
H H10C 0.7706 1.0888 0.5346 0.041 Uiso calc U . R 1
C C11 0.90768(13) 0.6490(4) 0.65739(10) 0.0341(7) Uani d . . . 1
H H11A 0.9057 0.5348 0.6644 0.051 Uiso calc U . R 1
H H11B 0.916 0.7137 0.6839 0.051 Uiso calc U . R 1
H H11C 0.9409 0.6654 0.6454 0.051 Uiso calc U . R 1
C C12 0.69095(13) 0.5158(4) 0.55884(12) 0.0345(7) Uani d . . . 1
H H12A 0.6535 0.551 0.5642 0.052 Uiso calc U . R 1
H H12B 0.704 0.4107 0.5726 0.052 Uiso calc U . R 1
H H12C 0.6823 0.5066 0.5274 0.052 Uiso calc U . R 1
C C13 0.70250(11) 1.0363(3) 0.66064(8) 0.0177(5) Uani d . . . 1
C C14 0.76270(13) 1.1273(4) 0.67231(10) 0.0299(6) Uani d . . . 1
H H14A 0.7949 1.0562 0.6691 0.045 Uiso calc U . R 1
H H14B 0.7748 1.1645 0.7026 0.045 Uiso calc U . R 1
H H14C 0.7576 1.2203 0.6529 0.045 Uiso calc U . R 1
C C15 0.67497(12) 1.0150(3) 0.69261(8) 0.0191(5) Uani d . . . 1
H H15 0.6958 1.0558 0.7211 0.023 Uiso calc U . R 1
C C16 0.61837(12) 0.9368(3) 0.68459(8) 0.0184(5) Uani d . . . 1
C C17 0.59089(15) 0.9278(4) 0.72042(9) 0.0314(7) Uani d . . . 1
H H17A 0.5527 0.9912 0.7122 0.047 Uiso calc U . R 1
H H17B 0.6205 0.971 0.7475 0.047 Uiso calc U . R 1
H H17C 0.5816 0.8152 0.7249 0.047 Uiso calc U . R 1
C C18 0.43884(11) 0.7101(3) 0.51569(7) 0.0164(5) Uani d . . . 1
H H18 0.4042 0.7195 0.4896 0.02 Uiso calc U . R 1
C C19 0.44690(11) 0.5952(3) 0.54659(8) 0.0176(5) Uani d . . . 1
H H19 0.4195 0.5089 0.5462 0.021 Uiso calc U . R 1
C C20 0.52939(10) 0.7629(3) 0.56716(7) 0.0116(4) Uani d . . . 1
C C21 0.51966(11) 0.5568(3) 0.62153(7) 0.0145(4) Uani d . . . 1
C C22 0.55933(12) 0.4248(3) 0.63257(8) 0.0200(5) Uani d . . . 1
C C23 0.57630(13) 0.3669(3) 0.67552(9) 0.0242(6) Uani d . . . 1
H H23 0.6048 0.28 0.6841 0.029 Uiso calc U . R 1
C C24 0.55296(12) 0.4320(3) 0.70564(8) 0.0214(5) Uani d . . . 1
C C25 0.50974(12) 0.5559(3) 0.69239(8) 0.0196(5) Uani d . . . 1
H H25 0.4914 0.597 0.7123 0.023 Uiso calc U . R 1
C C26 0.49286(11) 0.6208(3) 0.65073(8) 0.0158(4) Uani d . . . 1
C C27 0.58140(18) 0.3402(4) 0.59994(11) 0.0401(8) Uani d . . . 1
H H27A 0.5627 0.2328 0.594 0.06 Uiso calc U . R 1
H H27B 0.6266 0.3299 0.6117 0.06 Uiso calc U . R 1
H H27C 0.5694 0.4027 0.5728 0.06 Uiso calc U . R 1
C C28 0.57341(15) 0.3720(4) 0.75227(9) 0.0331(7) Uani d . . . 1
H H28A 0.5935 0.2668 0.7541 0.05 Uiso calc U . R 1
H H28B 0.5373 0.3615 0.7615 0.05 Uiso calc U . R 1
H H28C 0.6027 0.4489 0.7713 0.05 Uiso calc U . R 1
C C29 0.44820(12) 0.7601(3) 0.63756(9) 0.0220(5) Uani d . . . 1
H H29A 0.4285 0.7758 0.6596 0.033 Uiso calc U . R 1
H H29B 0.4165 0.7368 0.6093 0.033 Uiso calc U . R 1
H H29C 0.4706 0.8582 0.6352 0.033 Uiso calc U . R 1
C C30 0.10075(11) 0.3885(3) 0.47140(8) 0.0174(5) Uani d . . . 1
H H30 0.0805 0.4108 0.4413 0.021 Uiso calc U . R 1
C C31 0.15978(11) 0.3358(3) 0.48978(8) 0.0188(5) Uani d . . . 1
H H31 0.1884 0.3137 0.4753 0.023 Uiso calc U . R 1
C C32 0.11713(10) 0.3608(3) 0.54243(7) 0.0124(4) Uani d . . . 1
C C33 0.23058(10) 0.2893(3) 0.56498(8) 0.0155(4) Uani d . . . 1
C C34 0.27563(11) 0.4097(3) 0.57206(8) 0.0171(5) Uani d . . . 1
C C35 0.33517(11) 0.3765(3) 0.60056(8) 0.0195(5) Uani d . . . 1
H H35 0.3663 0.457 0.6056 0.023 Uiso calc U . R 1
C C36 0.35023(11) 0.2290(3) 0.62174(8) 0.0204(5) Uani d . . . 1
C C37 0.30431(12) 0.1133(3) 0.61433(9) 0.0233(5) Uani d . . . 1
H H37 0.3142 0.0126 0.6289 0.028 Uiso calc U . R 1
C C38 0.24378(11) 0.1403(3) 0.58597(9) 0.0195(5) Uani d . . . 1
C C39 0.26005(13) 0.5731(3) 0.55115(10) 0.0278(6) Uani d . . . 1
H H39A 0.2953 0.646 0.5635 0.042 Uiso calc U . R 1
H H39B 0.2238 0.6165 0.5567 0.042 Uiso calc U . R 1
H H39C 0.251 0.5633 0.5196 0.042 Uiso calc U . R 1
C C40 0.41520(12) 0.1985(4) 0.65268(10) 0.0308(7) Uani d . . . 1
H H40A 0.4226 0.2625 0.6792 0.046 Uiso calc U . R 1
H H40B 0.445 0.2294 0.6386 0.046 Uiso calc U . R 1
H H40C 0.4201 0.0838 0.6602 0.046 Uiso calc U . R 1
C C41 0.19491(13) 0.0136(3) 0.57911(11) 0.0315(7) Uani d . . . 1
H H41A 0.1683 0.0409 0.5961 0.047 Uiso calc U . R 1
H H41B 0.2146 -0.0911 0.5887 0.047 Uiso calc U . R 1
H H41C 0.1699 0.0081 0.5481 0.047 Uiso calc U . R 1
C C42 0.26641(13) 0.6105(4) 0.66831(9) 0.0304(6) Uani d . . . 1
H H42A 0.2971 0.5501 0.6598 0.046 Uiso calc U . R 1
H H42B 0.2835 0.6366 0.6994 0.046 Uiso calc U . R 1
H H42C 0.256 0.7104 0.6513 0.046 Uiso calc U . R 1
C C43 0.20897(11) 0.5097(3) 0.65963(8) 0.0194(5) Uani d . . . 1
C C44 0.19207(13) 0.4556(3) 0.69433(8) 0.0252(6) Uani d . . . 1
H H44 0.2189 0.4777 0.7232 0.03 Uiso calc U . R 1
C C45 0.13780(14) 0.3706(3) 0.68887(8) 0.0249(6) Uani d . . . 1
C C46 0.12408(17) 0.3166(4) 0.72890(9) 0.0405(8) Uani d . . . 1
H H46A 0.0822 0.3505 0.7265 0.061 Uiso calc U . R 1
H H46B 0.1541 0.3655 0.7549 0.061 Uiso calc U . R 1
H H46C 0.1271 0.199 0.7313 0.061 Uiso calc U . R 1
C C47 -0.06957(11) 0.2411(3) 0.52146(8) 0.0170(5) Uani d . . . 1
H H47 -0.1059 0.2622 0.4972 0.02 Uiso calc U . R 1
C C48 -0.06253(11) 0.1212(3) 0.55094(8) 0.0184(5) Uani d . . . 1
H H48 -0.0924 0.0424 0.5512 0.022 Uiso calc U . R 1
C C49 0.02649(10) 0.2646(3) 0.56911(7) 0.0122(4) Uani d . . . 1
C C50 0.01856(11) 0.0372(3) 0.61921(8) 0.0161(5) Uani d . . . 1
C C51 0.00308(12) 0.0838(3) 0.65545(8) 0.0211(5) Uani d . . . 1
C C52 0.02369(13) -0.0130(4) 0.69257(9) 0.0261(6) Uani d . . . 1
H H52 0.0135 0.0163 0.7175 0.031 Uiso calc U . R 1
C C53 0.05867(14) -0.1511(4) 0.69421(9) 0.0278(6) Uani d . . . 1
C C54 0.07079(12) -0.1966(3) 0.65697(9) 0.0235(5) Uani d . . . 1
H H54 0.0937 -0.2924 0.6575 0.028 Uiso calc U . R 1
C C55 0.05019(11) -0.1052(3) 0.61878(8) 0.0167(5) Uani d . . . 1
C C56 -0.03433(14) 0.2337(4) 0.65421(10) 0.0285(6) Uani d . . . 1
H H56A -0.0417 0.2454 0.6819 0.043 Uiso calc U . R 1
H H56B -0.0741 0.2256 0.6303 0.043 Uiso calc U . R 1
H H56C -0.0116 0.3279 0.6495 0.043 Uiso calc U . R 1
C C57 0.08195(18) -0.2517(5) 0.73521(11) 0.0478(10) Uani d . . . 1
H H57A 0.0488 -0.3231 0.7368 0.072 Uiso calc U . R 1
H H57B 0.0948 -0.1807 0.7608 0.072 Uiso calc U . R 1
H H57C 0.1173 -0.3167 0.7347 0.072 Uiso calc U . R 1
C C58 0.05937(12) -0.1642(3) 0.57779(9) 0.0225(5) Uani d . . . 1
H H58A 0.0236 -0.229 0.5609 0.034 Uiso calc U . R 1
H H58B 0.0969 -0.2303 0.5854 0.034 Uiso calc U . R 1
H H58C 0.0636 -0.0716 0.5603 0.034 Uiso calc U . R 1
C C59 0.71677(18) 0.6036(5) 0.73110(12) 0.0470(9) Uani d . . . 1
H H59A 0.7263 0.7099 0.7457 0.056 Uiso calc U . R 1
H H59B 0.6716 0.5858 0.7225 0.056 Uiso calc U . R 1
Cl Cl1 0.73796(5) 0.60583(12) 0.68360(3) 0.0521(2) Uani d . . . 1
Cl Cl2 0.75526(7) 0.45458(16) 0.76746(5) 0.0820(4) Uani d . . . 1
N N1 0.57911(9) 0.9283(2) 0.50510(6) 0.0137(4) Uani d . . . 1
N N2 0.67431(9) 0.8479(2) 0.53492(6) 0.0158(4) Uani d . . . 1
N N3 0.48945(9) 0.8114(2) 0.52843(6) 0.0128(4) Uani d . . . 1
N N4 0.50298(9) 0.6283(2) 0.57888(6) 0.0135(4) Uani d . . . 1
N N5 0.07511(9) 0.4042(2) 0.50385(6) 0.0129(4) Uani d . . . 1
N N6 0.17004(9) 0.3205(3) 0.53413(6) 0.0151(4) Uani d . . . 1
N N7 -0.01485(8) 0.3277(2) 0.53260(6) 0.0125(4) Uani d . . . 1
N N8 -0.00305(9) 0.1363(2) 0.58070(6) 0.0157(4) Uani d . . . 1
Ni Ni1 0.5 1.0 0.5 0.01024(8) Uani d . P S 1
Ni Ni2 0.60532(2) 0.86958(3) 0.59643(2) 0.01083(7) Uani d . . . 1
Ni Ni3 0 0.5 0.5 0.01018(8) Uani d . P S 1
Ni Ni4 0.10566(2) 0.35718(4) 0.59690(2) 0.01158(7) Uani d . . . 1
O O1 0.67997(8) 0.9857(2) 0.62165(5) 0.0162(3) Uani d . . . 1
O O2 0.58635(8) 0.8725(2) 0.64848(5) 0.0175(3) Uani d . . . 1
O O3 0.17938(8) 0.4792(2) 0.61954(5) 0.0173(3) Uani d . . . 1
O O4 0.09721(9) 0.3331(2) 0.65232(5) 0.0206(4) Uani d . . . 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'
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'
Cl Cl 0.1484 0.1585 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
C2 C1 N1 . . 108.2(2)
C2 C1 H1 . . 125.9
N1 C1 H1 . . 125.9
C1 C2 N2 . . 106.3(2)
C1 C2 H2 . . 126.9
N2 C2 H2 . . 126.9
N1 C3 N2 . . 106.08(19)
N1 C3 Ni2 . . 124.38(16)
N2 C3 Ni2 . . 129.36(17)
C9 C4 C5 . . 121.8(2)
C9 C4 N2 . . 119.2(2)
C5 C4 N2 . . 118.9(2)
C6 C5 C4 . . 117.7(2)
C6 C5 C10 . . 121.4(2)
C4 C5 C10 . . 120.9(2)
C5 C6 C7 . . 121.8(2)
C5 C6 H6 . . 119.1
C7 C6 H6 . . 119.1
C8 C7 C6 . . 118.6(2)
C8 C7 C11 . . 121.0(3)
C6 C7 C11 . . 120.4(3)
C7 C8 C9 . . 121.9(2)
C7 C8 H8 . . 119.1
C9 C8 H8 . . 119.1
C4 C9 C8 . . 118.1(2)
C4 C9 C12 . . 120.6(2)
C8 C9 C12 . . 121.3(2)
C5 C10 H10A . . 109.5
C5 C10 H10B . . 109.5
H10A C10 H10B . . 109.5
C5 C10 H10C . . 109.5
H10A C10 H10C . . 109.5
H10B C10 H10C . . 109.5
C7 C11 H11A . . 109.5
C7 C11 H11B . . 109.5
H11A C11 H11B . . 109.5
C7 C11 H11C . . 109.5
H11A C11 H11C . . 109.5
H11B C11 H11C . . 109.5
C9 C12 H12A . . 109.5
C9 C12 H12B . . 109.5
H12A C12 H12B . . 109.5
C9 C12 H12C . . 109.5
H12A C12 H12C . . 109.5
H12B C12 H12C . . 109.5
O1 C13 C15 . . 124.7(2)
O1 C13 C14 . . 116.4(2)
C15 C13 C14 . . 118.9(2)
C13 C14 H14A . . 109.5
C13 C14 H14B . . 109.5
H14A C14 H14B . . 109.5
C13 C14 H14C . . 109.5
H14A C14 H14C . . 109.5
H14B C14 H14C . . 109.5
C16 C15 C13 . . 123.1(2)
C16 C15 H15 . . 118.4
C13 C15 H15 . . 118.4
O2 C16 C15 . . 125.1(2)
O2 C16 C17 . . 115.7(2)
C15 C16 C17 . . 119.2(2)
C16 C17 H17A . . 109.5
C16 C17 H17B . . 109.5
H17A C17 H17B . . 109.5
C16 C17 H17C . . 109.5
H17A C17 H17C . . 109.5
H17B C17 H17C . . 109.5
C19 C18 N3 . . 108.5(2)
C19 C18 H18 . . 125.7
N3 C18 H18 . . 125.7
C18 C19 N4 . . 106.4(2)
C18 C19 H19 . . 126.8
N4 C19 H19 . . 126.8
N3 C20 N4 . . 106.07(19)
N3 C20 Ni2 . . 123.30(16)
N4 C20 Ni2 . . 130.63(16)
C22 C21 C26 . . 121.5(2)
C22 C21 N4 . . 120.6(2)
C26 C21 N4 . . 117.8(2)
C21 C22 C23 . . 117.5(2)
C21 C22 C27 . . 122.3(2)
C23 C22 C27 . . 120.1(2)
C24 C23 C22 . . 122.2(2)
C24 C23 H23 . . 118.9
C22 C23 H23 . . 118.9
C23 C24 C25 . . 118.5(2)
C23 C24 C28 . . 121.6(3)
C25 C24 C28 . . 119.9(2)
C26 C25 C24 . . 121.5(2)
C26 C25 H25 . . 119.3
C24 C25 H25 . . 119.3
C25 C26 C21 . . 118.5(2)
C25 C26 C29 . . 120.8(2)
C21 C26 C29 . . 120.7(2)
C22 C27 H27A . . 109.5
C22 C27 H27B . . 109.5
H27A C27 H27B . . 109.5
C22 C27 H27C . . 109.5
H27A C27 H27C . . 109.5
H27B C27 H27C . . 109.5
C24 C28 H28A . . 109.5
C24 C28 H28B . . 109.5
H28A C28 H28B . . 109.5
C24 C28 H28C . . 109.5
H28A C28 H28C . . 109.5
H28B C28 H28C . . 109.5
C26 C29 H29A . . 109.5
C26 C29 H29B . . 109.5
H29A C29 H29B . . 109.5
C26 C29 H29C . . 109.5
H29A C29 H29C . . 109.5
H29B C29 H29C . . 109.5
C31 C30 N5 . . 108.4(2)
C31 C30 H30 . . 125.8
N5 C30 H30 . . 125.8
C30 C31 N6 . . 106.2(2)
C30 C31 H31 . . 126.9
N6 C31 H31 . . 126.9
N5 C32 N6 . . 106.39(19)
N5 C32 Ni4 . . 126.76(16)
N6 C32 Ni4 . . 126.85(17)
C38 C33 C34 . . 121.7(2)
C38 C33 N6 . . 120.0(2)
C34 C33 N6 . . 118.2(2)
C35 C34 C33 . . 118.2(2)
C35 C34 C39 . . 120.5(2)
C33 C34 C39 . . 121.3(2)
C36 C35 C34 . . 121.8(2)
C36 C35 H35 . . 119.1
C34 C35 H35 . . 119.1
C37 C36 C35 . . 118.5(2)
C37 C36 C40 . . 121.4(2)
C35 C36 C40 . . 120.1(2)
C36 C37 C38 . . 122.0(2)
C36 C37 H37 . . 119.0
C38 C37 H37 . . 119.0
C33 C38 C37 . . 117.8(2)
C33 C38 C41 . . 121.4(2)
C37 C38 C41 . . 120.7(2)
C34 C39 H39A . . 109.5
C34 C39 H39B . . 109.5
H39A C39 H39B . . 109.5
C34 C39 H39C . . 109.5
H39A C39 H39C . . 109.5
H39B C39 H39C . . 109.5
C36 C40 H40A . . 109.5
C36 C40 H40B . . 109.5
H40A C40 H40B . . 109.5
C36 C40 H40C . . 109.5
H40A C40 H40C . . 109.5
H40B C40 H40C . . 109.5
C38 C41 H41A . . 109.5
C38 C41 H41B . . 109.5
H41A C41 H41B . . 109.5
C38 C41 H41C . . 109.5
H41A C41 H41C . . 109.5
H41B C41 H41C . . 109.5
C43 C42 H42A . . 109.5
C43 C42 H42B . . 109.5
H42A C42 H42B . . 109.5
C43 C42 H42C . . 109.5
H42A C42 H42C . . 109.5
H42B C42 H42C . . 109.5
O3 C43 C44 . . 124.8(2)
O3 C43 C42 . . 115.4(2)
C44 C43 C42 . . 119.8(2)
C43 C44 C45 . . 123.2(2)
C43 C44 H44 . . 118.4
C45 C44 H44 . . 118.4
O4 C45 C44 . . 125.6(2)
O4 C45 C46 . . 115.7(3)
C44 C45 C46 . . 118.8(2)
C45 C46 H46A . . 109.5
C45 C46 H46B . . 109.5
H46A C46 H46B . . 109.5
C45 C46 H46C . . 109.5
H46A C46 H46C . . 109.5
H46B C46 H46C . . 109.5
C48 C47 N7 . . 108.5(2)
C48 C47 H47 . . 125.8
N7 C47 H47 . . 125.8
C47 C48 N8 . . 106.3(2)
C47 C48 H48 . . 126.8
N8 C48 H48 . . 126.8
N7 C49 N8 . . 106.02(19)
N7 C49 Ni4 . . 122.45(16)
N8 C49 Ni4 . . 131.41(16)
C55 C50 C51 . . 121.8(2)
C55 C50 N8 . . 120.2(2)
C51 C50 N8 . . 117.8(2)
C52 C51 C50 . . 117.7(2)
C52 C51 C56 . . 121.4(2)
C50 C51 C56 . . 120.9(2)
C53 C52 C51 . . 121.9(2)
C53 C52 H52 . . 119.0
C51 C52 H52 . . 119.0
C54 C53 C52 . . 118.5(2)
C54 C53 C57 . . 120.5(3)
C52 C53 C57 . . 121.0(3)
C53 C54 C55 . . 121.7(3)
C53 C54 H54 . . 119.2
C55 C54 H54 . . 119.2
C50 C55 C54 . . 118.2(2)
C50 C55 C58 . . 121.2(2)
C54 C55 C58 . . 120.6(2)
C51 C56 H56A . . 109.5
C51 C56 H56B . . 109.5
H56A C56 H56B . . 109.5
C51 C56 H56C . . 109.5
H56A C56 H56C . . 109.5
H56B C56 H56C . . 109.5
C53 C57 H57A . . 109.5
C53 C57 H57B . . 109.5
H57A C57 H57B . . 109.5
C53 C57 H57C . . 109.5
H57A C57 H57C . . 109.5
H57B C57 H57C . . 109.5
C55 C58 H58A . . 109.5
C55 C58 H58B . . 109.5
H58A C58 H58B . . 109.5
C55 C58 H58C . . 109.5
H58A C58 H58C . . 109.5
H58B C58 H58C . . 109.5
Cl2 C59 Cl1 . . 112.1(2)
Cl2 C59 H59A . . 109.2
Cl1 C59 H59A . . 109.2
Cl2 C59 H59B . . 109.2
Cl1 C59 H59B . . 109.2
H59A C59 H59B . . 107.9
C3 N1 C1 . . 109.63(19)
C3 N1 Ni1 . . 122.85(15)
C1 N1 Ni1 . . 127.34(16)
C3 N2 C2 . . 109.77(19)
C3 N2 C4 . . 127.66(19)
C2 N2 C4 . . 122.54(19)
C20 N3 C18 . . 109.65(19)
C20 N3 Ni1 . . 123.48(16)
C18 N3 Ni1 . . 126.66(16)
C20 N4 C19 . . 109.38(19)
C20 N4 C21 . . 126.96(19)
C19 N4 C21 . . 121.69(19)
C32 N5 C30 . . 109.42(19)
C32 N5 Ni3 . . 121.94(15)
C30 N5 Ni3 . . 127.96(16)
C32 N6 C31 . . 109.56(19)
C32 N6 C33 . . 128.13(19)
C31 N6 C33 . . 121.74(19)
C49 N7 C47 . . 109.47(19)
C49 N7 Ni3 . . 125.75(16)
C47 N7 Ni3 . . 124.72(16)
C49 N8 C48 . . 109.71(19)
C49 N8 C50 . . 128.5(2)
C48 N8 C50 . . 121.6(2)
N1 Ni1 N1 . 3_676 180.0
N1 Ni1 N3 . 3_676 91.35(8)
N1 Ni1 N3 3_676 3_676 88.65(8)
N1 Ni1 N3 . . 88.65(8)
N1 Ni1 N3 3_676 . 91.35(8)
N3 Ni1 N3 3_676 . 180.00(12)
C3 Ni2 O2 . . 176.26(9)
C3 Ni2 O1 . . 87.56(9)
O2 Ni2 O1 . . 93.18(7)
C3 Ni2 C20 . . 88.88(9)
O2 Ni2 C20 . . 90.20(8)
O1 Ni2 C20 . . 175.55(8)
N5 Ni3 N5 3_566 . 180.0
N5 Ni3 N7 3_566 . 91.13(8)
N5 Ni3 N7 . . 88.87(8)
N5 Ni3 N7 3_566 3_566 88.87(8)
N5 Ni3 N7 . 3_566 91.13(8)
N7 Ni3 N7 . 3_566 180.0
C32 Ni4 O4 . . 174.48(9)
C32 Ni4 O3 . . 87.99(9)
O4 Ni4 O3 . . 93.06(8)
C32 Ni4 C49 . . 88.61(9)
O4 Ni4 C49 . . 91.12(8)
O3 Ni4 C49 . . 170.97(9)
C13 O1 Ni2 . . 127.10(16)
C16 O2 Ni2 . . 126.72(16)
C43 O3 Ni4 . . 126.79(17)
C45 O4 Ni4 . . 125.84(18)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
C1 C2 . 1.353(3)
C1 N1 . 1.384(3)
C1 H1 . 0.95
C2 N2 . 1.388(3)
C2 H2 . 0.95
C3 N1 . 1.347(3)
C3 N2 . 1.374(3)
C3 Ni2 . 1.887(2)
C4 C9 . 1.390(3)
C4 C5 . 1.408(3)
C4 N2 . 1.434(3)
C5 C6 . 1.393(3)
C5 C10 . 1.501(4)
C6 C7 . 1.393(4)
C6 H6 . 0.95
C7 C8 . 1.383(4)
C7 C11 . 1.515(4)
C8 C9 . 1.398(3)
C8 H8 . 0.95
C9 C12 . 1.498(4)
C10 H10A . 0.98
C10 H10B . 0.98
C10 H10C . 0.98
C11 H11A . 0.98
C11 H11B . 0.98
C11 H11C . 0.98
C12 H12A . 0.98
C12 H12B . 0.98
C12 H12C . 0.98
C13 O1 . 1.270(3)
C13 C15 . 1.403(4)
C13 C14 . 1.507(4)
C14 H14A . 0.98
C14 H14B . 0.98
C14 H14C . 0.98
C15 C16 . 1.396(4)
C15 H15 . 0.95
C16 O2 . 1.274(3)
C16 C17 . 1.508(4)
C17 H17A . 0.98
C17 H17B . 0.98
C17 H17C . 0.98
C18 C19 . 1.353(3)
C18 N3 . 1.379(3)
C18 H18 . 0.95
C19 N4 . 1.386(3)
C19 H19 . 0.95
C20 N3 . 1.345(3)
C20 N4 . 1.385(3)
C20 Ni2 . 1.899(2)
C21 C22 . 1.392(3)
C21 C26 . 1.403(3)
C21 N4 . 1.439(3)
C22 C23 . 1.404(4)
C22 C27 . 1.500(4)
C23 C24 . 1.380(4)
C23 H23 . 0.95
C24 C25 . 1.392(4)
C24 C28 . 1.515(4)
C25 C26 . 1.388(3)
C25 H25 . 0.95
C26 C29 . 1.508(3)
C27 H27A . 0.98
C27 H27B . 0.98
C27 H27C . 0.98
C28 H28A . 0.98
C28 H28B . 0.98
C28 H28C . 0.98
C29 H29A . 0.98
C29 H29B . 0.98
C29 H29C . 0.98
C30 C31 . 1.355(3)
C30 N5 . 1.382(3)
C30 H30 . 0.95
C31 N6 . 1.390(3)
C31 H31 . 0.95
C32 N5 . 1.348(3)
C32 N6 . 1.374(3)
C32 Ni4 . 1.883(2)
C33 C38 . 1.395(3)
C33 C34 . 1.400(3)
C33 N6 . 1.436(3)
C34 C35 . 1.395(3)
C34 C39 . 1.505(4)
C35 C36 . 1.390(4)
C35 H35 . 0.95
C36 C37 . 1.386(4)
C36 C40 . 1.512(3)
C37 C38 . 1.402(3)
C37 H37 . 0.95
C38 C41 . 1.499(4)
C39 H39A . 0.98
C39 H39B . 0.98
C39 H39C . 0.98
C40 H40A . 0.98
C40 H40B . 0.98
C40 H40C . 0.98
C41 H41A . 0.98
C41 H41B . 0.98
C41 H41C . 0.98
C42 C43 . 1.506(4)
C42 H42A . 0.98
C42 H42B . 0.98
C42 H42C . 0.98
C43 O3 . 1.277(3)
C43 C44 . 1.390(4)
C44 C45 . 1.390(4)
C44 H44 . 0.95
C45 O4 . 1.277(3)
C45 C46 . 1.511(4)
C46 H46A . 0.98
C46 H46B . 0.98
C46 H46C . 0.98
C47 C48 . 1.354(3)
C47 N7 . 1.385(3)
C47 H47 . 0.95
C48 N8 . 1.387(3)
C48 H48 . 0.95
C49 N7 . 1.350(3)
C49 N8 . 1.382(3)
C49 Ni4 . 1.897(2)
C50 C55 . 1.390(3)
C50 C51 . 1.400(3)
C50 N8 . 1.440(3)
C51 C52 . 1.394(4)
C51 C56 . 1.505(4)
C52 C53 . 1.390(4)
C52 H52 . 0.95
C53 C54 . 1.388(4)
C53 C57 . 1.512(4)
C54 C55 . 1.396(3)
C54 H54 . 0.95
C55 C58 . 1.504(3)
C56 H56A . 0.98
C56 H56B . 0.98
C56 H56C . 0.98
C57 H57A . 0.98
C57 H57B . 0.98
C57 H57C . 0.98
C58 H58A . 0.98
C58 H58B . 0.98
C58 H58C . 0.98
C59 Cl2 . 1.733(4)
C59 Cl1 . 1.775(4)
C59 H59A . 0.99
C59 H59B . 0.99
N1 Ni1 . 1.8659(18)
N3 Ni1 . 1.8759(19)
N5 Ni3 . 1.8655(18)
N7 Ni3 . 1.8807(19)
Ni1 N1 3_676 1.8660(18)
Ni1 N3 3_676 1.8758(19)
Ni2 O2 . 1.8912(16)
Ni2 O1 . 1.8938(17)
Ni3 N5 3_566 1.8654(18)
Ni3 N7 3_566 1.8807(19)
Ni4 O4 . 1.8931(17)
Ni4 O3 . 1.8944(17)
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_site_symmetry_4
_geom_torsion
N1 C1 C2 N2 . -0.7(3)
C9 C4 C5 C6 . -3.4(4)
N2 C4 C5 C6 . 179.9(2)
C9 C4 C5 C10 . 177.0(2)
N2 C4 C5 C10 . 0.3(3)
C4 C5 C6 C7 . 0.9(4)
C10 C5 C6 C7 . -179.5(3)
C5 C6 C7 C8 . 1.8(4)
C5 C6 C7 C11 . -178.0(3)
C6 C7 C8 C9 . -2.2(4)
C11 C7 C8 C9 . 177.6(3)
C5 C4 C9 C8 . 3.0(4)
N2 C4 C9 C8 . 179.7(2)
C5 C4 C9 C12 . -175.5(3)
N2 C4 C9 C12 . 1.2(4)
C7 C8 C9 C4 . -0.1(4)
C7 C8 C9 C12 . 178.4(3)
O1 C13 C15 C16 . -1.1(4)
C14 C13 C15 C16 . 178.0(3)
C13 C15 C16 O2 . 2.1(4)
C13 C15 C16 C17 . -176.7(3)
N3 C18 C19 N4 . 0.7(3)
C26 C21 C22 C23 . -5.9(4)
N4 C21 C22 C23 . 176.5(2)
C26 C21 C22 C27 . 171.2(3)
N4 C21 C22 C27 . -6.3(4)
C21 C22 C23 C24 . 2.9(4)
C27 C22 C23 C24 . -174.3(3)
C22 C23 C24 C25 . 2.0(4)
C22 C23 C24 C28 . -177.9(3)
C23 C24 C25 C26 . -4.0(4)
C28 C24 C25 C26 . 175.9(3)
C24 C25 C26 C21 . 1.1(4)
C24 C25 C26 C29 . -177.2(2)
C22 C21 C26 C25 . 4.0(4)
N4 C21 C26 C25 . -178.3(2)
C22 C21 C26 C29 . -177.8(2)
N4 C21 C26 C29 . -0.1(3)
N5 C30 C31 N6 . -0.4(3)
C38 C33 C34 C35 . 0.8(4)
N6 C33 C34 C35 . -177.2(2)
C38 C33 C34 C39 . -176.6(2)
N6 C33 C34 C39 . 5.4(3)
C33 C34 C35 C36 . -0.2(4)
C39 C34 C35 C36 . 177.3(2)
C34 C35 C36 C37 . -0.5(4)
C34 C35 C36 C40 . -179.5(2)
C35 C36 C37 C38 . 0.6(4)
C40 C36 C37 C38 . 179.6(3)
C34 C33 C38 C37 . -0.7(4)
N6 C33 C38 C37 . 177.2(2)
C34 C33 C38 C41 . 178.4(3)
N6 C33 C38 C41 . -3.6(4)
C36 C37 C38 C33 . 0.0(4)
C36 C37 C38 C41 . -179.1(3)
O3 C43 C44 C45 . -4.8(4)
C42 C43 C44 C45 . 175.9(3)
C43 C44 C45 O4 . -0.5(5)
C43 C44 C45 C46 . 179.7(3)
N7 C47 C48 N8 . 0.7(3)
C55 C50 C51 C52 . 3.7(4)
N8 C50 C51 C52 . 179.6(2)
C55 C50 C51 C56 . -176.5(2)
N8 C50 C51 C56 . -0.7(4)
C50 C51 C52 C53 . 0.3(4)
C56 C51 C52 C53 . -179.5(3)
C51 C52 C53 C54 . -2.9(4)
C51 C52 C53 C57 . 178.4(3)
C52 C53 C54 C55 . 1.7(4)
C57 C53 C54 C55 . -179.6(3)
C51 C50 C55 C54 . -4.9(4)
N8 C50 C55 C54 . 179.4(2)
C51 C50 C55 C58 . 172.1(2)
N8 C50 C55 C58 . -3.6(4)
C53 C54 C55 C50 . 2.1(4)
C53 C54 C55 C58 . -174.9(3)
N2 C3 N1 C1 . 0.3(3)
Ni2 C3 N1 C1 . 175.93(18)
N2 C3 N1 Ni1 . -175.10(16)
Ni2 C3 N1 Ni1 . 0.5(3)
C2 C1 N1 C3 . 0.3(3)
C2 C1 N1 Ni1 . 175.43(19)
N1 C3 N2 C2 . -0.8(3)
Ni2 C3 N2 C2 . -176.10(19)
N1 C3 N2 C4 . 177.4(2)
Ni2 C3 N2 C4 . 2.1(4)
C1 C2 N2 C3 . 1.0(3)
C1 C2 N2 C4 . -177.3(2)
C9 C4 N2 C3 . 79.0(3)
C5 C4 N2 C3 . -104.2(3)
C9 C4 N2 C2 . -103.0(3)
C5 C4 N2 C2 . 73.8(3)
N4 C20 N3 C18 . -0.1(2)
Ni2 C20 N3 C18 . -179.97(16)
N4 C20 N3 Ni1 . 174.86(14)
Ni2 C20 N3 Ni1 . -5.0(3)
C19 C18 N3 C20 . -0.4(3)
C19 C18 N3 Ni1 . -175.15(17)
N3 C20 N4 C19 . 0.5(2)
Ni2 C20 N4 C19 . -179.60(17)
N3 C20 N4 C21 . -163.5(2)
Ni2 C20 N4 C21 . 16.3(3)
C18 C19 N4 C20 . -0.8(3)
C18 C19 N4 C21 . 164.3(2)
C22 C21 N4 C20 . -97.5(3)
C26 C21 N4 C20 . 84.9(3)
C22 C21 N4 C19 . 100.3(3)
C26 C21 N4 C19 . -77.4(3)
N6 C32 N5 C30 . 1.1(3)
Ni4 C32 N5 C30 . -179.10(18)
N6 C32 N5 Ni3 . -170.12(15)
Ni4 C32 N5 Ni3 . 9.6(3)
C31 C30 N5 C32 . -0.5(3)
C31 C30 N5 Ni3 . 170.10(18)
N5 C32 N6 C31 . -1.4(3)
Ni4 C32 N6 C31 . 178.85(18)
N5 C32 N6 C33 . 169.9(2)
Ni4 C32 N6 C33 . -9.8(4)
C30 C31 N6 C32 . 1.1(3)
C30 C31 N6 C33 . -170.9(2)
C38 C33 N6 C32 . 78.9(3)
C34 C33 N6 C32 . -103.0(3)
C38 C33 N6 C31 . -110.7(3)
C34 C33 N6 C31 . 67.4(3)
N8 C49 N7 C47 . 0.2(2)
Ni4 C49 N7 C47 . -176.22(16)
N8 C49 N7 Ni3 . -177.07(15)
Ni4 C49 N7 Ni3 . 6.5(3)
C48 C47 N7 C49 . -0.6(3)
C48 C47 N7 Ni3 . 176.70(17)
N7 C49 N8 C48 . 0.3(3)
Ni4 C49 N8 C48 . 176.25(18)
N7 C49 N8 C50 . -174.0(2)
Ni4 C49 N8 C50 . 2.0(4)
C47 C48 N8 C49 . -0.6(3)
C47 C48 N8 C50 . 174.1(2)
C55 C50 N8 C49 . -92.7(3)
C51 C50 N8 C49 . 91.4(3)
C55 C50 N8 C48 . 93.7(3)
C51 C50 N8 C48 . -82.2(3)
C3 N1 Ni1 N3 3_676 129.34(19)
C1 N1 Ni1 N3 3_676 -45.3(2)
C3 N1 Ni1 N3 . -50.66(19)
C1 N1 Ni1 N3 . 134.7(2)
C20 N3 Ni1 N1 . 53.29(18)
C18 N3 Ni1 N1 . -132.6(2)
C20 N3 Ni1 N1 3_676 -126.71(18)
C18 N3 Ni1 N1 3_676 47.4(2)
N1 C3 Ni2 O1 . -128.8(2)
N2 C3 Ni2 O1 . 45.7(2)
N1 C3 Ni2 C20 . 48.5(2)
N2 C3 Ni2 C20 . -136.9(2)
N3 C20 Ni2 C3 . -45.71(19)
N4 C20 Ni2 C3 . 134.5(2)
N3 C20 Ni2 O2 . 130.67(19)
N4 C20 Ni2 O2 . -49.2(2)
C32 N5 Ni3 N7 . -53.09(19)
C30 N5 Ni3 N7 . 137.4(2)
C32 N5 Ni3 N7 3_566 126.92(19)
C30 N5 Ni3 N7 3_566 -42.6(2)
C49 N7 Ni3 N5 3_566 -134.63(19)
C47 N7 Ni3 N5 3_566 48.5(2)
C49 N7 Ni3 N5 . 45.37(19)
C47 N7 Ni3 N5 . -131.5(2)
N5 C32 Ni4 O3 . -129.0(2)
N6 C32 Ni4 O3 . 50.7(2)
N5 C32 Ni4 C49 . 42.7(2)
N6 C32 Ni4 C49 . -137.6(2)
N7 C49 Ni4 C32 . -50.00(19)
N8 C49 Ni4 C32 . 134.6(2)
N7 C49 Ni4 O4 . 135.51(19)
N8 C49 Ni4 O4 . -39.9(2)
C15 C13 O1 Ni2 . -0.3(4)
C14 C13 O1 Ni2 . -179.49(18)
C3 Ni2 O1 C13 . 177.0(2)
O2 Ni2 O1 C13 . 0.7(2)
C15 C16 O2 Ni2 . -1.6(4)
C17 C16 O2 Ni2 . 177.35(19)
O1 Ni2 O2 C16 . 0.2(2)
C20 Ni2 O2 C16 . -176.9(2)
C44 C43 O3 Ni4 . 0.8(4)
C42 C43 O3 Ni4 . -179.88(18)
C32 Ni4 O3 C43 . -169.5(2)
O4 Ni4 O3 C43 . 5.1(2)
C44 C45 O4 Ni4 . 9.1(4)
C46 C45 O4 Ni4 . -171.1(2)
O3 Ni4 O4 C45 . -9.9(2)
C49 Ni4 O4 C45 . 178.1(2)
