#------------------------------------------------------------------------------
#$Date: 2022-07-06 11:07:30 +0300 (Wed, 06 Jul 2022) $
#$Revision: 276611 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/71/04/7710439.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_7710439
loop_
_publ_author_name
'Schumann, Henrik'
'Klein, Marius'
'Prinzisky, Christian'
'Burghaus, Olaf'
'Sundermeyer, Jörg'
_publ_section_title
;
 Juglophen: a tetradentate non-innocent electron sponge
 naphthoquinone-imine ligand and its reduced and oxidized nickel complexes
 [Ni(jp)]<sup>-,0,+</sup> .
;
_journal_issue                   24
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              9348
_journal_page_last               9356
_journal_paper_doi               10.1039/d1dt03927j
_journal_volume                  51
_journal_year                    2022
_chemical_formula_moiety         '2(C26 H14 N2 Ni O4), C H2 Cl1.88'
_chemical_formula_sum            'C53 H30 Cl1.88 N4 Ni2 O8'
_chemical_formula_weight         1034.98
_chemical_name_common            '[Ni(juglophen)]'
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2021-07-13 deposited with the CCDC.	2022-06-07 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 102.081(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.3117(9)
_cell_length_b                   11.8026(7)
_cell_length_c                   22.8954(14)
_cell_measurement_reflns_used    9846
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.7130
_cell_measurement_theta_min      2.4847
_cell_volume                     4046.0(4)
_computing_cell_refinement
;
Bruker: APEX3 v2016.9-0, Bruker AXS Inc., 
Madison, Wisconsin, USA, 2015.
;
_computing_data_collection
;
Bruker: Bruker Instrument Service v3.0.26, Bruker AXS Inc., 
Madison, Wisconsin, USA, 2012.
;
_computing_data_reduction
;
Bruker: SAINT V8.27B, Bruker AXS Inc., 
Madison, Wisconsin, USA, 2012.
;
_computing_molecular_graphics
;
Mercury (C. F. Macrae, P. R. Edgington, P. McCabe, E. Pidcock, 
G. P. Shields, R. Taylor, M. Towler, 
J. van de Streek, J. Appl. Cryst. 2006,  39, 453-457.)
;
_computing_publication_material
;
WinGX 2014.1 (L.J. Farrugia, J. Appl. Cryst. 2012, 45, 849-854)
enCIFer (F. H. Allen, O. Johnson, G. P. Shields, 
B. R. Smith, M. Towler, J. Appl. Cryst. 2004, 37, 335-338.)
;
_computing_structure_refinement
;
SHELXL-2018/3, G. M. Sheldrick, Acta Cryst., 2015 C71, 3-8
;
_computing_structure_solution
;
SHELXT (Sheldrick, G. M. (2015). Acta Cryst. A71, 3-8.)
;
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 10.4167
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'D8 Quest (Bruker AXS Inc.)'
_diffrn_measurement_method       'rotation method'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0376
_diffrn_reflns_av_unetI/netI     0.0152
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            105532
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.025
_diffrn_reflns_theta_min         2.197
_diffrn_source                   'I\mS Microfocus Source'
_exptl_absorpt_coefficient_mu    1.125
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_correction_T_min  0.5877
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
'SADABS V2014/5 (Bruker AXS Inc.)'
;
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    1.699
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             2112
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: DCM'
_exptl_crystal_size_max          0.565
_exptl_crystal_size_mid          0.337
_exptl_crystal_size_min          0.232
_refine_diff_density_max         0.763
_refine_diff_density_min         -0.532
_refine_diff_density_rms         0.071
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.105
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     641
_refine_ls_number_reflns         7143
_refine_ls_number_restraints     12
_refine_ls_restrained_S_all      1.104
_refine_ls_R_factor_all          0.0363
_refine_ls_R_factor_gt           0.0335
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0319P)²+7.6033P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0840
_refine_ls_wR_factor_ref         0.0857
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6668
_reflns_number_total             7143
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1dt03927j2.cif
_cod_data_source_block           HSMA27_0m_a
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'Multi-Scan' was
changed to 'multi-scan' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 

 Adding full bibliography for 7710437--7710439.cif.
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7710439
_shelx_shelxl_version_number     2018/3
_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   0.569
_shelx_estimated_absorpt_t_max   0.780
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_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
_atom_site_disorder_assembly
_atom_site_disorder_group
Ni1 Ni 0.35336(2) 0.01647(2) 0.56188(2) 0.01018(9) Uani 1 1 d . . . . .
Cl1 Cl 0.25081(5) 0.68101(7) 0.39923(3) 0.0290(3) Uani 0.884(3) 1 d . . P . .
Ni2 Ni 0.10976(2) 0.00078(2) 0.51743(2) 0.01189(9) Uani 1 1 d . . . . .
O1 O 0.30324(11) -0.12118(13) 0.57336(7) 0.0146(3) Uani 1 1 d . . . . .
O2 O 0.35110(11) -0.03610(13) 0.48634(7) 0.0131(3) Uani 1 1 d . . . . .
O3 O 0.39435(14) -0.19946(18) 0.83756(9) 0.0339(5) Uani 1 1 d . . . . .
O4 O 0.53596(12) 0.31892(14) 0.36696(8) 0.0195(4) Uani 1 1 d . . . . .
O5 O 0.10460(11) -0.04921(14) 0.44090(7) 0.0163(4) Uani 1 1 d . . . . .
O6 O 0.07094(11) -0.14286(13) 0.52985(7) 0.0156(3) Uani 1 1 d . . . . .
O7 O 0.25778(13) 0.31757(16) 0.30903(8) 0.0259(4) Uani 1 1 d . . . . .
O8 O 0.05797(13) -0.17652(16) 0.79046(8) 0.0258(4) Uani 1 1 d . . . . .
N1 N 0.35986(12) 0.06516(16) 0.63995(8) 0.0113(4) Uani 1 1 d . . . . .
N2 N 0.40488(12) 0.15534(16) 0.55030(8) 0.0106(4) Uani 1 1 d . . . . .
N3 N 0.15306(13) 0.14444(16) 0.50360(8) 0.0115(4) Uani 1 1 d . . . . .
N4 N 0.11319(13) 0.04905(16) 0.59533(9) 0.0128(4) Uani 1 1 d . . . . .
C1 C 0.29892(15) -0.16586(19) 0.62467(10) 0.0131(5) Uani 1 1 d . . . . .
C2 C 0.25630(15) -0.2736(2) 0.62348(11) 0.0158(5) Uani 1 1 d . . . . .
H2 H 0.229904 -0.306554 0.586095 0.019 Uiso 1 1 calc R U . . .
C3 C 0.25261(16) -0.3305(2) 0.67506(11) 0.0170(5) Uani 1 1 d . . . . .
H3 H 0.222370 -0.401175 0.673061 0.020 Uiso 1 1 calc R U . . .
C4 C 0.29301(16) -0.2855(2) 0.73054(11) 0.0184(5) Uani 1 1 d . . . . .
H4 H 0.291158 -0.326101 0.766082 0.022 Uiso 1 1 calc R U . . .
C5 C 0.38220(17) -0.1398(2) 0.79286(11) 0.0216(5) Uani 1 1 d . . . . .
C6 C 0.41781(17) -0.0242(2) 0.79566(11) 0.0190(5) Uani 1 1 d . . . . .
H6 H 0.445765 0.006579 0.833271 0.023 Uiso 1 1 calc R U . . .
C7 C 0.41180(16) 0.0389(2) 0.74641(10) 0.0151(5) Uani 1 1 d . . . . .
H7 H 0.436926 0.112860 0.750049 0.018 Uiso 1 1 calc R U . . .
C8 C 0.36806(15) -0.00169(19) 0.68737(10) 0.0127(5) Uani 1 1 d . . . . .
C9 C 0.33603(15) -0.11702(19) 0.68104(10) 0.0131(5) Uani 1 1 d . . . . .
C10 C 0.33559(16) -0.1820(2) 0.73375(11) 0.0171(5) Uani 1 1 d . . . . .
C11 C 0.38542(15) 0.01288(19) 0.44537(10) 0.0117(5) Uani 1 1 d . . . . .
C12 C 0.37377(15) -0.0433(2) 0.38919(10) 0.0150(5) Uani 1 1 d . . . . .
H12 H 0.342975 -0.113591 0.383648 0.018 Uiso 1 1 calc R U . . .
C13 C 0.40634(16) 0.0027(2) 0.34288(11) 0.0163(5) Uani 1 1 d . . . . .
H13 H 0.398243 -0.036741 0.305960 0.020 Uiso 1 1 calc R U . . .
C14 C 0.45126(15) 0.1066(2) 0.34931(10) 0.0153(5) Uani 1 1 d . . . . .
H14 H 0.470083 0.139918 0.316228 0.018 Uiso 1 1 calc R U . . .
C15 C 0.51904(15) 0.2682(2) 0.41020(11) 0.0150(5) Uani 1 1 d . . . . .
C16 C 0.55066(16) 0.3096(2) 0.47153(11) 0.0164(5) Uani 1 1 d . . . . .
H16 H 0.595935 0.365947 0.479193 0.020 Uiso 1 1 calc R U . . .
C17 C 0.51690(15) 0.26950(19) 0.51667(10) 0.0141(5) Uani 1 1 d . . . . .
H17 H 0.536862 0.300515 0.555455 0.017 Uiso 1 1 calc R U . . .
C18 C 0.45001(15) 0.17910(19) 0.50806(10) 0.0110(4) Uani 1 1 d . . . . .
C19 C 0.43591(15) 0.11489(19) 0.45340(10) 0.0115(4) Uani 1 1 d . . . . .
C20 C 0.46804(15) 0.16048(19) 0.40404(10) 0.0127(5) Uani 1 1 d . . . . .
C21 C 0.36838(15) 0.18469(19) 0.64426(10) 0.0117(5) Uani 1 1 d . . . . .
C22 C 0.39478(15) 0.23423(19) 0.59506(10) 0.0114(4) Uani 1 1 d . . . . .
C23 C 0.39537(15) 0.35249(19) 0.58975(10) 0.0137(5) Uani 1 1 d . . . . .
H23 H 0.411878 0.386721 0.556097 0.016 Uiso 1 1 calc R U . . .
C24 C 0.37177(16) 0.4194(2) 0.63380(11) 0.0155(5) Uani 1 1 d . . . . .
H24 H 0.373316 0.499609 0.630673 0.019 Uiso 1 1 calc R U . . .
C25 C 0.34582(16) 0.3695(2) 0.68258(10) 0.0152(5) Uani 1 1 d . . . . .
H25 H 0.330241 0.415933 0.712720 0.018 Uiso 1 1 calc R U . . .
C26 C 0.34250(15) 0.2524(2) 0.68755(10) 0.0144(5) Uani 1 1 d . . . . .
H26 H 0.322759 0.218655 0.720188 0.017 Uiso 1 1 calc R U . . .
C27 C 0.12998(15) 0.00294(19) 0.39763(10) 0.0128(5) Uani 1 1 d . . . . .
C28 C 0.11446(16) -0.0524(2) 0.34103(10) 0.0167(5) Uani 1 1 d . . . . .
H28 H 0.086410 -0.124600 0.336913 0.020 Uiso 1 1 calc R U . . .
C29 C 0.13894(16) -0.0042(2) 0.29245(11) 0.0177(5) Uani 1 1 d . . . . .
H29 H 0.127668 -0.043283 0.255355 0.021 Uiso 1 1 calc R U . . .
C30 C 0.18039(16) 0.1021(2) 0.29693(10) 0.0171(5) Uani 1 1 d . . . . .
H30 H 0.196217 0.135576 0.262868 0.021 Uiso 1 1 calc R U . . .
C31 C 0.24250(16) 0.2697(2) 0.35367(11) 0.0168(5) Uani 1 1 d . . . . .
C32 C 0.27001(16) 0.3204(2) 0.41283(11) 0.0170(5) Uani 1 1 d . . . . .
H32 H 0.306843 0.385968 0.417703 0.020 Uiso 1 1 calc R U . . .
C33 C 0.24409(15) 0.27600(19) 0.46046(10) 0.0133(5) Uani 1 1 d . . . . .
H33 H 0.263334 0.311787 0.498124 0.016 Uiso 1 1 calc R U . . .
C34 C 0.18777(15) 0.17536(19) 0.45723(10) 0.0124(5) Uani 1 1 d . . . . .
C35 C 0.17326(15) 0.11050(19) 0.40289(10) 0.0121(5) Uani 1 1 d . . . . .
C36 C 0.19813(15) 0.1578(2) 0.35108(10) 0.0143(5) Uani 1 1 d . . . . .
C37 C 0.05453(15) -0.1840(2) 0.57935(10) 0.0136(5) Uani 1 1 d . . . . .
C38 C 0.01566(16) -0.2937(2) 0.57658(11) 0.0163(5) Uani 1 1 d . . . . .
H38 H 0.003866 -0.333226 0.539610 0.020 Uiso 1 1 calc R U . . .
C39 C -0.00531(16) -0.3442(2) 0.62593(11) 0.0180(5) Uani 1 1 d . . . . .
H39 H -0.032948 -0.416624 0.622392 0.022 Uiso 1 1 calc R U . . .
C40 C 0.01367(16) -0.2899(2) 0.68104(11) 0.0182(5) Uani 1 1 d . . . . .
H40 H -0.001938 -0.324568 0.714887 0.022 Uiso 1 1 calc R U . . .
C41 C 0.07938(16) -0.1341(2) 0.74654(11) 0.0175(5) Uani 1 1 d . . . . .
C42 C 0.13342(16) -0.0300(2) 0.75199(11) 0.0178(5) Uani 1 1 d . . . . .
H42 H 0.159089 -0.001212 0.790507 0.021 Uiso 1 1 calc R U . . .
C43 C 0.14694(16) 0.0248(2) 0.70336(10) 0.0154(5) Uani 1 1 d . . . . .
H43 H 0.181243 0.092505 0.708501 0.018 Uiso 1 1 calc R U . . .
C44 C 0.11084(15) -0.0157(2) 0.64253(10) 0.0127(5) Uani 1 1 d . . . . .
C45 C 0.07523(15) -0.1290(2) 0.63569(10) 0.0131(5) Uani 1 1 d . . . . .
C46 C 0.05517(15) -0.1856(2) 0.68646(11) 0.0154(5) Uani 1 1 d . . . . .
C47 C 0.14237(15) 0.2209(2) 0.54952(10) 0.0133(5) Uani 1 1 d . . . . .
C48 C 0.11874(15) 0.1685(2) 0.59936(10) 0.0134(5) Uani 1 1 d . . . . .
C49 C 0.09054(16) 0.2346(2) 0.64254(10) 0.0164(5) Uani 1 1 d . . . . .
H49 H 0.071036 0.199262 0.674833 0.020 Uiso 1 1 calc R U . . .
C50 C 0.09097(16) 0.3517(2) 0.63837(11) 0.0177(5) Uani 1 1 d . . . . .
H50 H 0.073998 0.396494 0.668629 0.021 Uiso 1 1 calc R U . . .
C51 C 0.11597(17) 0.4033(2) 0.59040(11) 0.0192(5) Uani 1 1 d . . . . .
H51 H 0.117358 0.483632 0.588222 0.023 Uiso 1 1 calc R U . . .
C52 C 0.13912(16) 0.3389(2) 0.54529(11) 0.0164(5) Uani 1 1 d . . . . .
H52 H 0.152848 0.375304 0.511308 0.020 Uiso 1 1 calc R U . . .
C53A C 0.1665(3) 0.7052(3) 0.4387(2) 0.0370(10) Uani 0.884(3) 1 d . . P A 1
H53A H 0.112079 0.731976 0.410690 0.044 Uiso 0.884(3) 1 calc R U P A 1
H53B H 0.185770 0.765476 0.468675 0.044 Uiso 0.884(3) 1 calc R U P A 1
Cl2A Cl 0.14122(9) 0.58158(7) 0.47491(4) 0.0401(3) Uani 0.884(3) 1 d . . P A 1
C53B C 0.209(3) 0.714(4) 0.456(2) 0.070(15) Uani 0.116(3) 1 d . U P A 2
H53C H 0.146973 0.741036 0.444120 0.084 Uiso 0.116(3) 1 calc R U P A 2
H53D H 0.245930 0.771987 0.481554 0.084 Uiso 0.116(3) 1 calc R U P A 2
Cl2B Cl 0.2166(17) 0.5782(10) 0.4918(7) 0.124(7) Uani 0.116(3) 1 d . U P A 2
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'
Cl Cl 0.1484 0.1585 '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'
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 Ni1 O1 84.82(7) . . ?
O2 Ni1 N1 177.36(8) . . ?
O1 Ni1 N1 94.33(8) . . ?
O2 Ni1 N2 95.08(8) . . ?
O1 Ni1 N2 179.60(8) . . ?
N1 Ni1 N2 85.75(8) . . ?
O5 Ni2 O6 84.29(7) . . ?
O5 Ni2 N4 178.73(8) . . ?
O6 Ni2 N4 94.54(8) . . ?
O5 Ni2 N3 94.34(8) . . ?
O6 Ni2 N3 177.70(8) . . ?
N4 Ni2 N3 86.84(8) . . ?
C1 O1 Ni1 126.04(15) . . ?
C11 O2 Ni1 126.81(15) . . ?
C27 O5 Ni2 128.22(15) . . ?
C37 O6 Ni2 127.22(15) . . ?
C8 N1 C21 122.9(2) . . ?
C8 N1 Ni1 125.42(16) . . ?
C21 N1 Ni1 111.08(15) . . ?
C18 N2 C22 122.62(19) . . ?
C18 N2 Ni1 126.07(16) . . ?
C22 N2 Ni1 111.21(14) . . ?
C34 N3 C47 122.8(2) . . ?
C34 N3 Ni2 126.64(16) . . ?
C47 N3 Ni2 110.51(14) . . ?
C44 N4 C48 122.1(2) . . ?
C44 N4 Ni2 127.02(16) . . ?
C48 N4 Ni2 110.90(15) . . ?
O1 C1 C9 124.7(2) . . ?
O1 C1 C2 116.9(2) . . ?
C9 C1 C2 118.3(2) . . ?
C3 C2 C1 121.5(2) . . ?
C3 C2 H2 119.3 . . ?
C1 C2 H2 119.3 . . ?
C2 C3 C4 120.4(2) . . ?
C2 C3 H3 119.8 . . ?
C4 C3 H3 119.8 . . ?
C10 C4 C3 120.0(2) . . ?
C10 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
O3 C5 C6 120.6(2) . . ?
O3 C5 C10 122.1(2) . . ?
C6 C5 C10 117.2(2) . . ?
C7 C6 C5 121.5(2) . . ?
C7 C6 H6 119.3 . . ?
C5 C6 H6 119.3 . . ?
C6 C7 C8 122.3(2) . . ?
C6 C7 H7 118.8 . . ?
C8 C7 H7 118.8 . . ?
N1 C8 C9 120.4(2) . . ?
N1 C8 C7 120.6(2) . . ?
C9 C8 C7 118.9(2) . . ?
C1 C9 C10 118.5(2) . . ?
C1 C9 C8 122.5(2) . . ?
C10 C9 C8 118.8(2) . . ?
C4 C10 C9 121.0(2) . . ?
C4 C10 C5 118.7(2) . . ?
C9 C10 C5 120.3(2) . . ?
O2 C11 C19 125.0(2) . . ?
O2 C11 C12 116.8(2) . . ?
C19 C11 C12 118.2(2) . . ?
C13 C12 C11 121.1(2) . . ?
C13 C12 H12 119.5 . . ?
C11 C12 H12 119.5 . . ?
C12 C13 C14 121.0(2) . . ?
C12 C13 H13 119.5 . . ?
C14 C13 H13 119.5 . . ?
C20 C14 C13 119.5(2) . . ?
C20 C14 H14 120.2 . . ?
C13 C14 H14 120.2 . . ?
O4 C15 C16 121.6(2) . . ?
O4 C15 C20 122.4(2) . . ?
C16 C15 C20 116.0(2) . . ?
C17 C16 C15 121.2(2) . . ?
C17 C16 H16 119.4 . . ?
C15 C16 H16 119.4 . . ?
C16 C17 C18 121.9(2) . . ?
C16 C17 H17 119.1 . . ?
C18 C17 H17 119.1 . . ?
N2 C18 C19 121.0(2) . . ?
N2 C18 C17 120.7(2) . . ?
C19 C18 C17 118.3(2) . . ?
C11 C19 C20 119.0(2) . . ?
C11 C19 C18 122.4(2) . . ?
C20 C19 C18 118.4(2) . . ?
C14 C20 C19 121.0(2) . . ?
C14 C20 C15 118.4(2) . . ?
C19 C20 C15 120.6(2) . . ?
C26 C21 C22 120.4(2) . . ?
C26 C21 N1 125.7(2) . . ?
C22 C21 N1 113.4(2) . . ?
C23 C22 C21 119.6(2) . . ?
C23 C22 N2 126.0(2) . . ?
C21 C22 N2 113.6(2) . . ?
C24 C23 C22 119.8(2) . . ?
C24 C23 H23 120.1 . . ?
C22 C23 H23 120.1 . . ?
C23 C24 C25 120.3(2) . . ?
C23 C24 H24 119.9 . . ?
C25 C24 H24 119.9 . . ?
C26 C25 C24 120.6(2) . . ?
C26 C25 H25 119.7 . . ?
C24 C25 H25 119.7 . . ?
C25 C26 C21 119.4(2) . . ?
C25 C26 H26 120.3 . . ?
C21 C26 H26 120.3 . . ?
O5 C27 C35 124.6(2) . . ?
O5 C27 C28 117.3(2) . . ?
C35 C27 C28 118.1(2) . . ?
C29 C28 C27 121.7(2) . . ?
C29 C28 H28 119.1 . . ?
C27 C28 H28 119.1 . . ?
C28 C29 C30 120.6(2) . . ?
C28 C29 H29 119.7 . . ?
C30 C29 H29 119.7 . . ?
C36 C30 C29 119.6(2) . . ?
C36 C30 H30 120.2 . . ?
C29 C30 H30 120.2 . . ?
O7 C31 C32 120.9(2) . . ?
O7 C31 C36 122.8(2) . . ?
C32 C31 C36 116.4(2) . . ?
C33 C32 C31 121.1(2) . . ?
C33 C32 H32 119.5 . . ?
C31 C32 H32 119.5 . . ?
C32 C33 C34 123.2(2) . . ?
C32 C33 H33 118.4 . . ?
C34 C33 H33 118.4 . . ?
N3 C34 C35 121.9(2) . . ?
N3 C34 C33 120.8(2) . . ?
C35 C34 C33 117.4(2) . . ?
C27 C35 C36 118.5(2) . . ?
C27 C35 C34 122.2(2) . . ?
C36 C35 C34 119.3(2) . . ?
C30 C36 C35 121.4(2) . . ?
C30 C36 C31 117.6(2) . . ?
C35 C36 C31 120.9(2) . . ?
O6 C37 C45 124.9(2) . . ?
O6 C37 C38 117.1(2) . . ?
C45 C37 C38 118.0(2) . . ?
C39 C38 C37 121.7(2) . . ?
C39 C38 H38 119.1 . . ?
C37 C38 H38 119.1 . . ?
C38 C39 C40 120.4(2) . . ?
C38 C39 H39 119.8 . . ?
C40 C39 H39 119.8 . . ?
C46 C40 C39 119.9(2) . . ?
C46 C40 H40 120.1 . . ?
C39 C40 H40 120.1 . . ?
O8 C41 C42 120.9(2) . . ?
O8 C41 C46 122.4(2) . . ?
C42 C41 C46 116.7(2) . . ?
C43 C42 C41 120.9(2) . . ?
C43 C42 H42 119.5 . . ?
C41 C42 H42 119.5 . . ?
C42 C43 C44 122.6(2) . . ?
C42 C43 H43 118.7 . . ?
C44 C43 H43 118.7 . . ?
N4 C44 C45 121.3(2) . . ?
N4 C44 C43 121.0(2) . . ?
C45 C44 C43 117.7(2) . . ?
C37 C45 C46 118.7(2) . . ?
C37 C45 C44 122.1(2) . . ?
C46 C45 C44 119.1(2) . . ?
C40 C46 C45 121.2(2) . . ?
C40 C46 C41 118.2(2) . . ?
C45 C46 C41 120.7(2) . . ?
C52 C47 C48 118.8(2) . . ?
C52 C47 N3 126.2(2) . . ?
C48 C47 N3 114.1(2) . . ?
C49 C48 C47 119.8(2) . . ?
C49 C48 N4 125.5(2) . . ?
C47 C48 N4 114.0(2) . . ?
C50 C49 C48 120.1(2) . . ?
C50 C49 H49 119.9 . . ?
C48 C49 H49 119.9 . . ?
C51 C50 C49 120.1(2) . . ?
C51 C50 H50 119.9 . . ?
C49 C50 H50 119.9 . . ?
C50 C51 C52 120.5(2) . . ?
C50 C51 H51 119.7 . . ?
C52 C51 H51 119.7 . . ?
C51 C52 C47 120.4(2) . . ?
C51 C52 H52 119.8 . . ?
C47 C52 H52 119.8 . . ?
Cl1 C53A Cl2A 111.5(2) . . ?
Cl1 C53A H53A 109.3 . . ?
Cl2A C53A H53A 109.3 . . ?
Cl1 C53A H53B 109.3 . . ?
Cl2A C53A H53B 109.3 . . ?
H53A C53A H53B 108.0 . . ?
Cl1 C53B Cl2B 99(3) . . ?
Cl1 C53B H53C 112.0 . . ?
Cl2B C53B H53C 112.0 . . ?
Cl1 C53B H53D 112.0 . . ?
Cl2B C53B H53D 112.0 . . ?
H53C C53B H53D 109.7 . . ?
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 O2 1.8309(16) . ?
Ni1 O1 1.8390(16) . ?
Ni1 N1 1.8603(19) . ?
Ni1 N2 1.8619(19) . ?
Cl1 C53B 1.61(5) . ?
Cl1 C53A 1.747(4) . ?
Ni2 O5 1.8347(16) . ?
Ni2 O6 1.8383(16) . ?
Ni2 N4 1.8625(19) . ?
Ni2 N3 1.8716(19) . ?
O1 C1 1.302(3) . ?
O2 C11 1.303(3) . ?
O3 C5 1.224(3) . ?
O4 C15 1.230(3) . ?
O5 C27 1.293(3) . ?
O6 C37 1.305(3) . ?
O7 C31 1.233(3) . ?
O8 C41 1.228(3) . ?
N1 C8 1.327(3) . ?
N1 C21 1.418(3) . ?
N2 C18 1.331(3) . ?
N2 C22 1.417(3) . ?
N3 C34 1.334(3) . ?
N3 C47 1.421(3) . ?
N4 C44 1.330(3) . ?
N4 C48 1.414(3) . ?
C1 C9 1.419(3) . ?
C1 C2 1.427(3) . ?
C2 C3 1.370(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.397(4) . ?
C3 H3 0.9500 . ?
C4 C10 1.379(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.466(4) . ?
C5 C10 1.478(4) . ?
C6 C7 1.339(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.458(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.444(3) . ?
C9 C10 1.432(3) . ?
C11 C19 1.422(3) . ?
C11 C12 1.425(3) . ?
C12 C13 1.374(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.399(3) . ?
C13 H13 0.9500 . ?
C14 C20 1.381(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.470(3) . ?
C15 C20 1.483(3) . ?
C16 C17 1.335(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.463(3) . ?
C17 H17 0.9500 . ?
C18 C19 1.440(3) . ?
C19 C20 1.429(3) . ?
C21 C26 1.393(3) . ?
C21 C22 1.402(3) . ?
C22 C23 1.401(3) . ?
C23 C24 1.387(3) . ?
C23 H23 0.9500 . ?
C24 C25 1.392(3) . ?
C24 H24 0.9500 . ?
C25 C26 1.389(3) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
C27 C35 1.425(3) . ?
C27 C28 1.426(3) . ?
C28 C29 1.369(4) . ?
C28 H28 0.9500 . ?
C29 C30 1.400(4) . ?
C29 H29 0.9500 . ?
C30 C36 1.380(3) . ?
C30 H30 0.9500 . ?
C31 C32 1.460(3) . ?
C31 C36 1.480(3) . ?
C32 C33 1.343(3) . ?
C32 H32 0.9500 . ?
C33 C34 1.461(3) . ?
C33 H33 0.9500 . ?
C34 C35 1.438(3) . ?
C35 C36 1.433(3) . ?
C37 C45 1.419(3) . ?
C37 C38 1.421(3) . ?
C38 C39 1.373(3) . ?
C38 H38 0.9500 . ?
C39 C40 1.391(4) . ?
C39 H39 0.9500 . ?
C40 C46 1.379(4) . ?
C40 H40 0.9500 . ?
C41 C42 1.472(4) . ?
C41 C46 1.479(3) . ?
C42 C43 1.340(3) . ?
C42 H42 0.9500 . ?
C43 C44 1.467(3) . ?
C43 H43 0.9500 . ?
C44 C45 1.441(3) . ?
C45 C46 1.429(3) . ?
C47 C52 1.396(3) . ?
C47 C48 1.410(3) . ?
C48 C49 1.397(3) . ?
C49 C50 1.385(3) . ?
C49 H49 0.9500 . ?
C50 C51 1.378(4) . ?
C50 H50 0.9500 . ?
C51 C52 1.387(3) . ?
C51 H51 0.9500 . ?
C52 H52 0.9500 . ?
C53A Cl2A 1.762(4) . ?
C53A H53A 0.9900 . ?
C53A H53B 0.9900 . ?
C53B Cl2B 1.79(5) . ?
C53B H53C 0.9900 . ?
C53B H53D 0.9900 . ?
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
O2 Ni1 O1 C1 163.89(18) . . . . ?
N1 Ni1 O1 C1 -13.60(18) . . . . ?
O1 Ni1 O2 C11 -173.65(18) . . . . ?
N2 Ni1 O2 C11 5.96(19) . . . . ?
O6 Ni2 O5 C27 -174.2(2) . . . . ?
N3 Ni2 O5 C27 3.9(2) . . . . ?
O5 Ni2 O6 C37 -179.58(19) . . . . ?
N4 Ni2 O6 C37 -0.07(19) . . . . ?
O1 Ni1 N1 C8 28.32(19) . . . . ?
N2 Ni1 N1 C8 -151.28(19) . . . . ?
O1 Ni1 N1 C21 -160.44(15) . . . . ?
N2 Ni1 N1 C21 19.96(15) . . . . ?
O2 Ni1 N2 C18 -19.86(19) . . . . ?
N1 Ni1 N2 C18 157.63(19) . . . . ?
O2 Ni1 N2 C22 163.54(14) . . . . ?
N1 Ni1 N2 C22 -18.98(15) . . . . ?
O5 Ni2 N3 C34 -15.0(2) . . . . ?
N4 Ni2 N3 C34 165.4(2) . . . . ?
O5 Ni2 N3 C47 163.58(15) . . . . ?
N4 Ni2 N3 C47 -15.97(15) . . . . ?
O6 Ni2 N4 C44 15.3(2) . . . . ?
N3 Ni2 N4 C44 -162.9(2) . . . . ?
O6 Ni2 N4 C48 -164.63(15) . . . . ?
N3 Ni2 N4 C48 17.21(16) . . . . ?
Ni1 O1 C1 C9 -2.8(3) . . . . ?
Ni1 O1 C1 C2 179.49(15) . . . . ?
O1 C1 C2 C3 176.4(2) . . . . ?
C9 C1 C2 C3 -1.5(3) . . . . ?
C1 C2 C3 C4 -1.8(3) . . . . ?
C2 C3 C4 C10 1.2(4) . . . . ?
O3 C5 C6 C7 174.3(3) . . . . ?
C10 C5 C6 C7 -2.8(4) . . . . ?
C5 C6 C7 C8 1.4(4) . . . . ?
C21 N1 C8 C9 163.5(2) . . . . ?
Ni1 N1 C8 C9 -26.3(3) . . . . ?
C21 N1 C8 C7 -18.3(3) . . . . ?
Ni1 N1 C8 C7 151.93(17) . . . . ?
C6 C7 C8 N1 177.0(2) . . . . ?
C6 C7 C8 C9 -4.8(3) . . . . ?
O1 C1 C9 C10 -172.6(2) . . . . ?
C2 C1 C9 C10 5.1(3) . . . . ?
O1 C1 C9 C8 12.1(3) . . . . ?
C2 C1 C9 C8 -170.2(2) . . . . ?
N1 C8 C9 C1 3.2(3) . . . . ?
C7 C8 C9 C1 -175.1(2) . . . . ?
N1 C8 C9 C10 -172.2(2) . . . . ?
C7 C8 C9 C10 9.6(3) . . . . ?
C3 C4 C10 C9 2.7(4) . . . . ?
C3 C4 C10 C5 -176.5(2) . . . . ?
C1 C9 C10 C4 -5.8(3) . . . . ?
C8 C9 C10 C4 169.7(2) . . . . ?
C1 C9 C10 C5 173.3(2) . . . . ?
C8 C9 C10 C5 -11.2(3) . . . . ?
O3 C5 C10 C4 9.9(4) . . . . ?
C6 C5 C10 C4 -173.1(2) . . . . ?
O3 C5 C10 C9 -169.3(2) . . . . ?
C6 C5 C10 C9 7.8(3) . . . . ?
Ni1 O2 C11 C19 3.7(3) . . . . ?
Ni1 O2 C11 C12 -178.79(15) . . . . ?
O2 C11 C12 C13 179.0(2) . . . . ?
C19 C11 C12 C13 -3.3(3) . . . . ?
C11 C12 C13 C14 -0.6(4) . . . . ?
C12 C13 C14 C20 4.1(3) . . . . ?
O4 C15 C16 C17 165.4(2) . . . . ?
C20 C15 C16 C17 -16.3(3) . . . . ?
C15 C16 C17 C18 2.8(4) . . . . ?
C22 N2 C18 C19 -159.8(2) . . . . ?
Ni1 N2 C18 C19 24.0(3) . . . . ?
C22 N2 C18 C17 21.7(3) . . . . ?
Ni1 N2 C18 C17 -154.53(17) . . . . ?
C16 C17 C18 N2 -167.0(2) . . . . ?
C16 C17 C18 C19 14.5(3) . . . . ?
O2 C11 C19 C20 -178.7(2) . . . . ?
C12 C11 C19 C20 3.8(3) . . . . ?
O2 C11 C19 C18 -3.7(3) . . . . ?
C12 C11 C19 C18 178.7(2) . . . . ?
N2 C18 C19 C11 -10.6(3) . . . . ?
C17 C18 C19 C11 168.0(2) . . . . ?
N2 C18 C19 C20 164.4(2) . . . . ?
C17 C18 C19 C20 -17.1(3) . . . . ?
C13 C14 C20 C19 -3.5(3) . . . . ?
C13 C14 C20 C15 177.5(2) . . . . ?
C11 C19 C20 C14 -0.4(3) . . . . ?
C18 C19 C20 C14 -175.6(2) . . . . ?
C11 C19 C20 C15 178.5(2) . . . . ?
C18 C19 C20 C15 3.3(3) . . . . ?
O4 C15 C20 C14 10.3(3) . . . . ?
C16 C15 C20 C14 -168.0(2) . . . . ?
O4 C15 C20 C19 -168.6(2) . . . . ?
C16 C15 C20 C19 13.0(3) . . . . ?
C8 N1 C21 C26 -33.9(3) . . . . ?
Ni1 N1 C21 C26 154.63(19) . . . . ?
C8 N1 C21 C22 154.6(2) . . . . ?
Ni1 N1 C21 C22 -16.9(2) . . . . ?
C26 C21 C22 C23 0.3(3) . . . . ?
N1 C21 C22 C23 172.3(2) . . . . ?
C26 C21 C22 N2 -170.2(2) . . . . ?
N1 C21 C22 N2 1.8(3) . . . . ?
C18 N2 C22 C23 27.6(3) . . . . ?
Ni1 N2 C22 C23 -155.7(2) . . . . ?
C18 N2 C22 C21 -162.7(2) . . . . ?
Ni1 N2 C22 C21 14.0(2) . . . . ?
C21 C22 C23 C24 1.4(3) . . . . ?
N2 C22 C23 C24 170.6(2) . . . . ?
C22 C23 C24 C25 -1.3(4) . . . . ?
C23 C24 C25 C26 -0.5(4) . . . . ?
C24 C25 C26 C21 2.2(4) . . . . ?
C22 C21 C26 C25 -2.1(3) . . . . ?
N1 C21 C26 C25 -173.0(2) . . . . ?
Ni2 O5 C27 C35 4.1(3) . . . . ?
Ni2 O5 C27 C28 -176.84(16) . . . . ?
O5 C27 C28 C29 -180.0(2) . . . . ?
C35 C27 C28 C29 -0.8(3) . . . . ?
C27 C28 C29 C30 0.0(4) . . . . ?
C28 C29 C30 C36 1.1(4) . . . . ?
O7 C31 C32 C33 171.7(2) . . . . ?
C36 C31 C32 C33 -9.8(3) . . . . ?
C31 C32 C33 C34 0.2(4) . . . . ?
C47 N3 C34 C35 -160.2(2) . . . . ?
Ni2 N3 C34 C35 18.3(3) . . . . ?
C47 N3 C34 C33 21.2(3) . . . . ?
Ni2 N3 C34 C33 -160.33(16) . . . . ?
C32 C33 C34 N3 -170.0(2) . . . . ?
C32 C33 C34 C35 11.4(3) . . . . ?
O5 C27 C35 C36 179.6(2) . . . . ?
C28 C27 C35 C36 0.6(3) . . . . ?
O5 C27 C35 C34 -4.1(3) . . . . ?
C28 C27 C35 C34 176.8(2) . . . . ?
N3 C34 C35 C27 -7.4(3) . . . . ?
C33 C34 C35 C27 171.2(2) . . . . ?
N3 C34 C35 C36 168.8(2) . . . . ?
C33 C34 C35 C36 -12.6(3) . . . . ?
C29 C30 C36 C35 -1.4(3) . . . . ?
C29 C30 C36 C31 179.7(2) . . . . ?
C27 C35 C36 C30 0.5(3) . . . . ?
C34 C35 C36 C30 -175.8(2) . . . . ?
C27 C35 C36 C31 179.4(2) . . . . ?
C34 C35 C36 C31 3.1(3) . . . . ?
O7 C31 C36 C30 5.5(3) . . . . ?
C32 C31 C36 C30 -172.9(2) . . . . ?
O7 C31 C36 C35 -173.4(2) . . . . ?
C32 C31 C36 C35 8.1(3) . . . . ?
Ni2 O6 C37 C45 -8.9(3) . . . . ?
Ni2 O6 C37 C38 173.26(16) . . . . ?
O6 C37 C38 C39 -179.2(2) . . . . ?
C45 C37 C38 C39 2.8(3) . . . . ?
C37 C38 C39 C40 -2.0(4) . . . . ?
C38 C39 C40 C46 -1.1(4) . . . . ?
O8 C41 C42 C43 -171.1(2) . . . . ?
C46 C41 C42 C43 10.7(3) . . . . ?
C41 C42 C43 C44 -1.2(4) . . . . ?
C48 N4 C44 C45 158.4(2) . . . . ?
Ni2 N4 C44 C45 -21.5(3) . . . . ?
C48 N4 C44 C43 -23.5(3) . . . . ?
Ni2 N4 C44 C43 156.64(17) . . . . ?
C42 C43 C44 N4 169.3(2) . . . . ?
C42 C43 C44 C45 -12.5(3) . . . . ?
O6 C37 C45 C46 -178.6(2) . . . . ?
C38 C37 C45 C46 -0.7(3) . . . . ?
O6 C37 C45 C44 5.2(4) . . . . ?
C38 C37 C45 C44 -177.0(2) . . . . ?
N4 C44 C45 C37 10.4(3) . . . . ?
C43 C44 C45 C37 -167.8(2) . . . . ?
N4 C44 C45 C46 -165.8(2) . . . . ?
C43 C44 C45 C46 15.9(3) . . . . ?
C39 C40 C46 C45 3.2(3) . . . . ?
C39 C40 C46 C41 -176.2(2) . . . . ?
C37 C45 C46 C40 -2.2(3) . . . . ?
C44 C45 C46 C40 174.2(2) . . . . ?
C37 C45 C46 C41 177.1(2) . . . . ?
C44 C45 C46 C41 -6.5(3) . . . . ?
O8 C41 C46 C40 -5.6(4) . . . . ?
C42 C41 C46 C40 172.6(2) . . . . ?
O8 C41 C46 C45 175.0(2) . . . . ?
C42 C41 C46 C45 -6.8(3) . . . . ?
C34 N3 C47 C52 20.9(4) . . . . ?
Ni2 N3 C47 C52 -157.8(2) . . . . ?
C34 N3 C47 C48 -169.9(2) . . . . ?
Ni2 N3 C47 C48 11.4(2) . . . . ?
C52 C47 C48 C49 1.6(3) . . . . ?
N3 C47 C48 C49 -168.5(2) . . . . ?
C52 C47 C48 N4 172.2(2) . . . . ?
N3 C47 C48 N4 2.1(3) . . . . ?
C44 N4 C48 C49 -24.7(4) . . . . ?
Ni2 N4 C48 C49 155.2(2) . . . . ?
C44 N4 C48 C47 165.3(2) . . . . ?
Ni2 N4 C48 C47 -14.8(2) . . . . ?
C47 C48 C49 C50 -3.9(4) . . . . ?
N4 C48 C49 C50 -173.4(2) . . . . ?
C48 C49 C50 C51 2.5(4) . . . . ?
C49 C50 C51 C52 1.3(4) . . . . ?
C50 C51 C52 C47 -3.7(4) . . . . ?
C48 C47 C52 C51 2.2(4) . . . . ?
N3 C47 C52 C51 170.9(2) . . . . ?
