#------------------------------------------------------------------------------
#$Date: 2022-04-12 02:11:16 +0300 (Tue, 12 Apr 2022) $
#$Revision: 274459 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/70/99/7709983.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_7709983
loop_
_publ_author_name
'Wang, Zhen-Feng'
'Wei, Qiao-Chang'
'Li, Jin-Xian'
'Zhou, Zhen'
'Zhang, Shuhua'
_publ_section_title
;
 A new class of nickel(II) oxyquinoline-bipyridine complexes as potent
 anticancer agents induces apoptosis and autophagy in A549/DDP tumor cells
 through mitophagy pathways
;
_journal_name_full               'Dalton Transactions'
_journal_paper_doi               10.1039/D2DT00669C
_journal_year                    2022
_chemical_formula_moiety         'C44 H28 Cl4 N4 Ni O2, 2(C H4 O)'
_chemical_formula_sum            'C46 H36 Cl4 N4 Ni O4'
_chemical_formula_weight         909.30
_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     iterative
_audit_creation_date             2021-07-17
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2022-04-02 deposited with the CCDC.	2022-04-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 110.7596(17)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   19.1813(8)
_cell_length_b                   15.3203(7)
_cell_length_c                   14.7737(5)
_cell_measurement_reflns_used    6355
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      25.81
_cell_measurement_theta_min      2.53
_cell_volume                     4059.6(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_temperature      150.0
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0891
_diffrn_reflns_av_unetI/netI     0.0437
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            66978
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.396
_diffrn_reflns_theta_min         2.011
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.792
_exptl_absorpt_correction_T_max  0.0276
_exptl_absorpt_correction_T_min  0.0114
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0865 before and 0.0699 after correction.
The Ratio of minimum to maximum transmission is 0.4130.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.488
_exptl_crystal_description       block
_exptl_crystal_F_000             1872
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.468
_refine_diff_density_min         -0.575
_refine_diff_density_rms         0.079
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     538
_refine_ls_number_reflns         8295
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.097
_refine_ls_R_factor_all          0.0700
_refine_ls_R_factor_gt           0.0524
_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)+(0.0718P)²+1.2498P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1242
_refine_ls_wR_factor_ref         0.1353
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6543
_reflns_number_total             8295
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2dt00669c2.cif
_cod_data_source_block           ni14
_cod_database_code               7709983
_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_max   0.890
_shelx_estimated_absorpt_t_min   0.763
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C18(H18), C34(H34), C12(H12), C21(H21), C38(H38), C16(H16), C30(H30),
 C28(H28), C40(H40), C27(H27), C37(H37), C17(H17), C36(H36), C7(H7), C35(H35),
 C44(H44), C8(H8), C41(H41), C3(H3), C9(H9), C42(H42), C43(H43)
2.b Idealised Me refined as rotating group:
 C32(H32A,H32B,H32C), C19(H19A,H19B,H19C), C45(H45A,H45B,H45C), C46(H46A,H46B,
 H46C)
2.c Idealised tetrahedral OH refined as rotating group:
 O3(H3A), O4(H4)
;
_olex2_submission_special_instructions 'No special instructions were received'
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 0.25408(2) 0.38684(2) 0.41703(3) 0.02373(11) Uani 1 1 d . . . . .
Cl3 Cl 0.40946(4) 0.56637(5) 0.27615(5) 0.03203(17) Uani 1 1 d . . . . .
Cl1 Cl 0.05699(5) 0.24140(7) 0.52298(7) 0.0512(3) Uani 1 1 d . . . . .
Cl4 Cl 0.14440(6) 0.62835(7) -0.00544(7) 0.0566(3) Uani 1 1 d . . . . .
Cl2 Cl 0.04167(7) 0.56071(10) 0.66548(7) 0.0714(4) Uani 1 1 d . . . . .
O1 O 0.17775(12) 0.32222(14) 0.46221(15) 0.0311(5) Uani 1 1 d . . . . .
O2 O 0.31891(11) 0.46283(13) 0.36608(15) 0.0273(4) Uani 1 1 d . . . . .
N4 N 0.28596(13) 0.26217(15) 0.37896(17) 0.0242(5) Uani 1 1 d . . . . .
N1 N 0.21284(14) 0.49141(17) 0.47429(18) 0.0299(5) Uani 1 1 d . . . . .
N3 N 0.34226(13) 0.34913(16) 0.54639(17) 0.0260(5) Uani 1 1 d . . . . .
N2 N 0.17329(14) 0.42814(16) 0.28644(17) 0.0260(5) Uani 1 1 d . . . . .
O3 O 0.11554(18) 0.1878(2) 0.3390(2) 0.0611(8) Uani 1 1 d . . . . .
H3A H 0.127996 0.226555 0.382014 0.092 Uiso 1 1 calc GR . . . .
O4 O -0.0232(2) 0.2459(2) 0.2158(3) 0.0746(10) Uani 1 1 d . . . . .
H4 H 0.018949 0.226638 0.249787 0.112 Uiso 1 1 calc GR . . . .
C11 C 0.31308(17) 0.55143(19) 0.2307(2) 0.0289(6) Uani 1 1 d . . . . .
C15 C 0.20281(16) 0.48496(18) 0.2386(2) 0.0259(6) Uani 1 1 d . . . . .
C33 C 0.47630(17) 0.22598(19) 0.8143(2) 0.0276(6) Uani 1 1 d . . . . .
C10 C 0.28214(16) 0.49881(18) 0.2841(2) 0.0256(6) Uani 1 1 d . . . . .
C18 C 0.08162(19) 0.5057(2) 0.1156(2) 0.0376(7) Uani 1 1 d . . . . .
H18 H 0.049533 0.532428 0.057866 0.045 Uiso 1 1 calc R . . . .
C14 C 0.15877(18) 0.5246(2) 0.1504(2) 0.0314(7) Uani 1 1 d . . . . .
C34 C 0.54988(18) 0.2535(2) 0.8591(2) 0.0352(7) Uani 1 1 d . . . . .
H34 H 0.570167 0.295670 0.828229 0.042 Uiso 1 1 calc R . . . .
C25 C 0.32187(16) 0.21406(19) 0.4597(2) 0.0259(6) Uani 1 1 d . . . . .
C31 C 0.26460(16) 0.22190(19) 0.2933(2) 0.0263(6) Uani 1 1 d . . . . .
C24 C 0.35233(16) 0.26092(19) 0.5501(2) 0.0246(6) Uani 1 1 d . . . . .
C22 C 0.43001(16) 0.2659(2) 0.7202(2) 0.0278(6) Uani 1 1 d . . . . .
C12 C 0.27133(19) 0.5905(2) 0.1430(2) 0.0355(7) Uani 1 1 d . . . . .
H12 H 0.295368 0.625790 0.109911 0.043 Uiso 1 1 calc R . . . .
C21 C 0.42313(17) 0.3547(2) 0.7121(2) 0.0284(6) Uani 1 1 d . . . . .
H21 H 0.448728 0.389907 0.766772 0.034 Uiso 1 1 calc R . . . .
C38 C 0.44783(18) 0.1639(2) 0.8603(2) 0.0299(6) Uani 1 1 d . . . . .
H38 H 0.397981 0.144034 0.830538 0.036 Uiso 1 1 calc R . . . .
C23 C 0.39443(16) 0.21577(19) 0.6349(2) 0.0261(6) Uani 1 1 d . . . . .
C16 C 0.10147(17) 0.4107(2) 0.2508(2) 0.0293(6) Uani 1 1 d . . . . .
H16 H 0.081349 0.370769 0.284258 0.035 Uiso 1 1 calc R . . . .
C4 C 0.0791(2) 0.4903(3) 0.6017(3) 0.0503(10) Uani 1 1 d . . . . .
C13 C 0.1959(2) 0.5782(2) 0.1044(2) 0.0371(7) Uani 1 1 d . . . . .
C30 C 0.27457(17) 0.1311(2) 0.2861(2) 0.0281(6) Uani 1 1 d . . . . .
H30 H 0.256736 0.104176 0.224226 0.034 Uiso 1 1 calc R . . . .
C28 C 0.40174(18) 0.1231(2) 0.6314(2) 0.0307(6) Uani 1 1 d . . . . .
H28 H 0.427139 0.091783 0.689215 0.037 Uiso 1 1 calc R . . . .
C40 C 0.3939(2) -0.0482(2) 0.3821(3) 0.0386(7) Uani 1 1 d . . . . .
H40 H 0.435720 -0.012333 0.414580 0.046 Uiso 1 1 calc R . . . .
C27 C 0.37292(18) 0.0793(2) 0.5466(2) 0.0316(7) Uani 1 1 d . . . . .
H27 H 0.378142 0.017673 0.546253 0.038 Uiso 1 1 calc R . . . .
C39 C 0.32187(19) -0.0135(2) 0.3539(2) 0.0330(7) Uani 1 1 d . . . . .
C26 C 0.33482(17) 0.1236(2) 0.4576(2) 0.0290(6) Uani 1 1 d . . . . .
C37 C 0.4921(2) 0.1309(2) 0.9496(2) 0.0345(7) Uani 1 1 d . . . . .
H37 H 0.472094 0.089046 0.981155 0.041 Uiso 1 1 calc R . . . .
C32 C 0.23258(18) 0.2738(2) 0.2027(2) 0.0308(6) Uani 1 1 d . . . . .
H32A H 0.180515 0.288131 0.192256 0.046 Uiso 1 1 calc GR . . . .
H32B H 0.234937 0.239578 0.147777 0.046 Uiso 1 1 calc GR . . . .
H32C H 0.261226 0.327772 0.208359 0.046 Uiso 1 1 calc GR . . . .
C6 C 0.16270(17) 0.4648(2) 0.5147(2) 0.0331(7) Uani 1 1 d . . . . .
C17 C 0.05336(18) 0.4494(2) 0.1646(2) 0.0361(7) Uani 1 1 d . . . . .
H17 H 0.001624 0.436044 0.141075 0.043 Uiso 1 1 calc R . . . .
C20 C 0.37927(17) 0.3956(2) 0.6252(2) 0.0280(6) Uani 1 1 d . . . . .
C36 C 0.5647(2) 0.1584(2) 0.9930(2) 0.0394(8) Uani 1 1 d . . . . .
H36 H 0.594949 0.135079 1.053890 0.047 Uiso 1 1 calc R . . . .
C29 C 0.30923(17) 0.0811(2) 0.3661(2) 0.0306(6) Uani 1 1 d . . . . .
C1 C 0.14498(17) 0.3734(2) 0.5055(2) 0.0333(7) Uani 1 1 d . . . . .
C7 C 0.2259(2) 0.5752(2) 0.4700(2) 0.0385(7) Uani 1 1 d . . . . .
H7 H 0.259711 0.593242 0.439754 0.046 Uiso 1 1 calc R . . . .
C35 C 0.5934(2) 0.2200(2) 0.9477(2) 0.0415(8) Uani 1 1 d . . . . .
H35 H 0.643384 0.239399 0.977659 0.050 Uiso 1 1 calc R . . . .
C44 C 0.2619(2) -0.0675(2) 0.3069(3) 0.0416(8) Uani 1 1 d . . . . .
H44 H 0.212537 -0.045107 0.287041 0.050 Uiso 1 1 calc R . . . .
C5 C 0.1284(2) 0.5247(3) 0.5592(2) 0.0414(8) Uani 1 1 d . . . . .
C2 C 0.09070(18) 0.3476(3) 0.5424(2) 0.0400(8) Uani 1 1 d . . . . .
C8 C 0.1916(2) 0.6394(2) 0.5084(3) 0.0477(9) Uani 1 1 d . . . . .
H8 H 0.201524 0.699589 0.502971 0.057 Uiso 1 1 calc R . . . .
C41 C 0.4043(2) -0.1344(2) 0.3628(3) 0.0462(9) Uani 1 1 d . . . . .
H41 H 0.453431 -0.157425 0.381844 0.055 Uiso 1 1 calc R . . . .
C3 C 0.0601(2) 0.4041(3) 0.5926(3) 0.0511(11) Uani 1 1 d . . . . .
H3 H 0.025885 0.382410 0.620498 0.061 Uiso 1 1 calc R . . . .
C19 C 0.37574(19) 0.4929(2) 0.6206(2) 0.0351(7) Uani 1 1 d . . . . .
H19A H 0.366691 0.512031 0.554117 0.053 Uiso 1 1 calc GR . . . .
H19B H 0.423094 0.517197 0.663836 0.053 Uiso 1 1 calc GR . . . .
H19C H 0.335108 0.513315 0.640884 0.053 Uiso 1 1 calc GR . . . .
C9 C 0.1443(2) 0.6140(3) 0.5534(3) 0.0519(10) Uani 1 1 d . . . . .
H9 H 0.121877 0.656568 0.581043 0.062 Uiso 1 1 calc R . . . .
C42 C 0.3444(3) -0.1873(2) 0.3165(3) 0.0500(10) Uani 1 1 d . . . . .
H42 H 0.352127 -0.246624 0.303666 0.060 Uiso 1 1 calc R . . . .
C43 C 0.2737(2) -0.1544(2) 0.2889(3) 0.0499(9) Uani 1 1 d . . . . .
H43 H 0.232287 -0.191133 0.257112 0.060 Uiso 1 1 calc R . . . .
C45 C 0.1230(3) 0.1043(3) 0.3832(5) 0.0741(15) Uani 1 1 d . . . . .
H45A H 0.115778 0.058884 0.333947 0.111 Uiso 1 1 calc GR . . . .
H45B H 0.085401 0.097647 0.413552 0.111 Uiso 1 1 calc GR . . . .
H45C H 0.172881 0.098656 0.432522 0.111 Uiso 1 1 calc GR . . . .
C46 C -0.0775(3) 0.2057(4) 0.2432(4) 0.0711(13) Uani 1 1 d . . . . .
H46A H -0.126371 0.230704 0.206404 0.107 Uiso 1 1 calc GR . . . .
H46B H -0.066424 0.215076 0.312570 0.107 Uiso 1 1 calc GR . . . .
H46C H -0.077992 0.142946 0.230163 0.107 Uiso 1 1 calc GR . . . .
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
O1 Ni1 N4 87.62(9) . . ?
O1 Ni1 N1 79.83(10) . . ?
O1 Ni1 N3 90.48(9) . . ?
O1 Ni1 N2 93.70(9) . . ?
O2 Ni1 O1 172.50(9) . . ?
O2 Ni1 N4 98.31(9) . . ?
O2 Ni1 N1 94.58(9) . . ?
O2 Ni1 N3 95.27(9) . . ?
O2 Ni1 N2 80.57(9) . . ?
N1 Ni1 N4 166.67(10) . . ?
N1 Ni1 N3 97.95(10) . . ?
N1 Ni1 N2 83.06(10) . . ?
N3 Ni1 N4 77.54(9) . . ?
N2 Ni1 N4 102.36(9) . . ?
N2 Ni1 N3 175.80(9) . . ?
C1 O1 Ni1 113.0(2) . . ?
C10 O2 Ni1 112.95(18) . . ?
C25 N4 Ni1 110.83(18) . . ?
C31 N4 Ni1 129.9(2) . . ?
C31 N4 C25 118.0(2) . . ?
C6 N1 Ni1 112.0(2) . . ?
C7 N1 Ni1 128.5(2) . . ?
C7 N1 C6 119.3(3) . . ?
C24 N3 Ni1 111.11(19) . . ?
C20 N3 Ni1 130.1(2) . . ?
C20 N3 C24 118.0(3) . . ?
C15 N2 Ni1 111.19(19) . . ?
C16 N2 Ni1 129.3(2) . . ?
C16 N2 C15 119.4(3) . . ?
C45 O3 H3A 109.5 . . ?
C46 O4 H4 109.5 . . ?
C10 C11 Cl3 117.6(2) . . ?
C12 C11 Cl3 118.9(2) . . ?
C12 C11 C10 123.6(3) . . ?
N2 C15 C10 114.5(3) . . ?
N2 C15 C14 122.0(3) . . ?
C14 C15 C10 123.5(3) . . ?
C34 C33 C22 119.1(3) . . ?
C38 C33 C34 118.9(3) . . ?
C38 C33 C22 122.0(3) . . ?
O2 C10 C11 125.2(3) . . ?
O2 C10 C15 120.6(3) . . ?
C11 C10 C15 114.2(3) . . ?
C14 C18 H18 120.0 . . ?
C17 C18 H18 120.0 . . ?
C17 C18 C14 120.1(3) . . ?
C18 C14 C15 116.9(3) . . ?
C13 C14 C15 117.2(3) . . ?
C13 C14 C18 125.9(3) . . ?
C33 C34 H34 119.7 . . ?
C35 C34 C33 120.6(3) . . ?
C35 C34 H34 119.7 . . ?
N4 C25 C24 117.0(3) . . ?
N4 C25 C26 123.4(3) . . ?
C26 C25 C24 119.5(3) . . ?
N4 C31 C30 121.4(3) . . ?
N4 C31 C32 119.7(3) . . ?
C30 C31 C32 118.8(3) . . ?
N3 C24 C25 116.8(2) . . ?
N3 C24 C23 123.4(3) . . ?
C23 C24 C25 119.7(3) . . ?
C21 C22 C33 119.8(3) . . ?
C21 C22 C23 117.2(3) . . ?
C23 C22 C33 123.0(3) . . ?
C11 C12 H12 119.9 . . ?
C13 C12 C11 120.2(3) . . ?
C13 C12 H12 119.9 . . ?
C22 C21 H21 119.0 . . ?
C22 C21 C20 122.0(3) . . ?
C20 C21 H21 119.0 . . ?
C33 C38 H38 120.0 . . ?
C37 C38 C33 120.1(3) . . ?
C37 C38 H38 120.0 . . ?
C24 C23 C22 117.8(3) . . ?
C24 C23 C28 119.2(3) . . ?
C22 C23 C28 123.0(3) . . ?
N2 C16 H16 118.9 . . ?
N2 C16 C17 122.2(3) . . ?
C17 C16 H16 118.9 . . ?
C5 C4 Cl2 118.6(4) . . ?
C3 C4 Cl2 120.3(3) . . ?
C3 C4 C5 121.1(3) . . ?
C14 C13 Cl4 119.2(3) . . ?
C12 C13 Cl4 119.5(3) . . ?
C12 C13 C14 121.3(3) . . ?
C31 C30 H30 119.2 . . ?
C29 C30 C31 121.6(3) . . ?
C29 C30 H30 119.2 . . ?
C23 C28 H28 119.6 . . ?
C27 C28 C23 120.8(3) . . ?
C27 C28 H28 119.6 . . ?
C39 C40 H40 119.9 . . ?
C41 C40 H40 119.9 . . ?
C41 C40 C39 120.1(3) . . ?
C28 C27 H27 119.2 . . ?
C28 C27 C26 121.6(3) . . ?
C26 C27 H27 119.2 . . ?
C40 C39 C29 121.3(3) . . ?
C44 C39 C40 118.6(3) . . ?
C44 C39 C29 119.9(3) . . ?
C25 C26 C27 118.9(3) . . ?
C25 C26 C29 117.8(3) . . ?
C29 C26 C27 123.3(3) . . ?
C38 C37 H37 119.7 . . ?
C36 C37 C38 120.6(3) . . ?
C36 C37 H37 119.7 . . ?
C31 C32 H32A 109.5 . . ?
C31 C32 H32B 109.5 . . ?
C31 C32 H32C 109.5 . . ?
H32A C32 H32B 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
N1 C6 C1 115.6(3) . . ?
N1 C6 C5 121.6(3) . . ?
C5 C6 C1 122.8(3) . . ?
C18 C17 C16 119.4(3) . . ?
C18 C17 H17 120.3 . . ?
C16 C17 H17 120.3 . . ?
N3 C20 C21 121.3(3) . . ?
N3 C20 C19 119.5(3) . . ?
C21 C20 C19 119.2(3) . . ?
C37 C36 H36 120.2 . . ?
C37 C36 C35 119.6(3) . . ?
C35 C36 H36 120.2 . . ?
C30 C29 C39 119.4(3) . . ?
C30 C29 C26 117.6(3) . . ?
C26 C29 C39 123.0(3) . . ?
O1 C1 C6 119.5(3) . . ?
O1 C1 C2 125.3(3) . . ?
C2 C1 C6 115.1(3) . . ?
N1 C7 H7 118.7 . . ?
N1 C7 C8 122.6(3) . . ?
C8 C7 H7 118.7 . . ?
C34 C35 C36 120.3(3) . . ?
C34 C35 H35 119.9 . . ?
C36 C35 H35 119.9 . . ?
C39 C44 H44 119.9 . . ?
C39 C44 C43 120.3(4) . . ?
C43 C44 H44 119.9 . . ?
C4 C5 C6 117.3(4) . . ?
C4 C5 C9 125.7(3) . . ?
C9 C5 C6 116.9(3) . . ?
C1 C2 Cl1 119.2(3) . . ?
C1 C2 C3 123.0(4) . . ?
C3 C2 Cl1 117.8(3) . . ?
C7 C8 H8 120.5 . . ?
C9 C8 C7 119.0(4) . . ?
C9 C8 H8 120.5 . . ?
C40 C41 H41 119.7 . . ?
C42 C41 C40 120.7(4) . . ?
C42 C41 H41 119.7 . . ?
C4 C3 C2 120.3(3) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C20 C19 H19A 109.5 . . ?
C20 C19 H19B 109.5 . . ?
C20 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C5 C9 H9 119.8 . . ?
C8 C9 C5 120.3(3) . . ?
C8 C9 H9 119.8 . . ?
C41 C42 H42 120.1 . . ?
C43 C42 C41 119.8(3) . . ?
C43 C42 H42 120.1 . . ?
C44 C43 H43 119.8 . . ?
C42 C43 C44 120.5(4) . . ?
C42 C43 H43 119.8 . . ?
O3 C45 H45A 109.5 . . ?
O3 C45 H45B 109.5 . . ?
O3 C45 H45C 109.5 . . ?
H45A C45 H45B 109.5 . . ?
H45A C45 H45C 109.5 . . ?
H45B C45 H45C 109.5 . . ?
O4 C46 H46A 109.5 . . ?
O4 C46 H46B 109.5 . . ?
O4 C46 H46C 109.5 . . ?
H46A C46 H46B 109.5 . . ?
H46A C46 H46C 109.5 . . ?
H46B C46 H46C 109.5 . . ?
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 O1 2.064(2) . ?
Ni1 O2 2.033(2) . ?
Ni1 N4 2.141(2) . ?
Ni1 N1 2.093(2) . ?
Ni1 N3 2.134(2) . ?
Ni1 N2 2.099(2) . ?
Cl3 C11 1.744(3) . ?
Cl1 C2 1.737(4) . ?
Cl4 C13 1.749(3) . ?
Cl2 C4 1.746(4) . ?
O1 C1 1.306(4) . ?
O2 C10 1.290(3) . ?
N4 C25 1.363(4) . ?
N4 C31 1.335(4) . ?
N1 C6 1.361(4) . ?
N1 C7 1.314(4) . ?
N3 C24 1.364(4) . ?
N3 C20 1.334(4) . ?
N2 C15 1.364(4) . ?
N2 C16 1.316(4) . ?
O3 H3A 0.8400 . ?
O3 C45 1.421(6) . ?
O4 H4 0.8400 . ?
O4 C46 1.387(5) . ?
C11 C10 1.398(4) . ?
C11 C12 1.395(4) . ?
C15 C10 1.445(4) . ?
C15 C14 1.415(4) . ?
C33 C34 1.395(4) . ?
C33 C22 1.490(4) . ?
C33 C38 1.388(4) . ?
C18 H18 0.9500 . ?
C18 C14 1.414(5) . ?
C18 C17 1.357(5) . ?
C14 C13 1.409(5) . ?
C34 H34 0.9500 . ?
C34 C35 1.378(5) . ?
C25 C24 1.445(4) . ?
C25 C26 1.410(4) . ?
C31 C30 1.413(4) . ?
C31 C32 1.490(4) . ?
C24 C23 1.408(4) . ?
C22 C21 1.369(4) . ?
C22 C23 1.426(4) . ?
C12 H12 0.9500 . ?
C12 C13 1.368(5) . ?
C21 H21 0.9500 . ?
C21 C20 1.408(4) . ?
C38 H38 0.9500 . ?
C38 C37 1.387(4) . ?
C23 C28 1.430(4) . ?
C16 H16 0.9500 . ?
C16 C17 1.411(4) . ?
C4 C5 1.410(6) . ?
C4 C3 1.363(6) . ?
C30 H30 0.9500 . ?
C30 C29 1.367(4) . ?
C28 H28 0.9500 . ?
C28 C27 1.354(4) . ?
C40 H40 0.9500 . ?
C40 C39 1.399(5) . ?
C40 C41 1.381(5) . ?
C27 H27 0.9500 . ?
C27 C26 1.429(4) . ?
C39 C29 1.491(4) . ?
C39 C44 1.387(5) . ?
C26 C29 1.421(4) . ?
C37 H37 0.9500 . ?
C37 C36 1.377(5) . ?
C32 H32A 0.9800 . ?
C32 H32B 0.9800 . ?
C32 H32C 0.9800 . ?
C6 C1 1.436(5) . ?
C6 C5 1.420(5) . ?
C17 H17 0.9500 . ?
C20 C19 1.492(4) . ?
C36 H36 0.9500 . ?
C36 C35 1.379(5) . ?
C1 C2 1.392(4) . ?
C7 H7 0.9500 . ?
C7 C8 1.409(5) . ?
C35 H35 0.9500 . ?
C44 H44 0.9500 . ?
C44 C43 1.392(5) . ?
C5 C9 1.411(6) . ?
C2 C3 1.398(5) . ?
C8 H8 0.9500 . ?
C8 C9 1.357(6) . ?
C41 H41 0.9500 . ?
C41 C42 1.374(6) . ?
C3 H3 0.9500 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C9 H9 0.9500 . ?
C42 H42 0.9500 . ?
C42 C43 1.367(6) . ?
C43 H43 0.9500 . ?
C45 H45A 0.9800 . ?
C45 H45B 0.9800 . ?
C45 H45C 0.9800 . ?
C46 H46A 0.9800 . ?
C46 H46B 0.9800 . ?
C46 H46C 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
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Ni1 O1 C1 C6 1.6(3) . . . . ?
Ni1 O1 C1 C2 179.3(3) . . . . ?
Ni1 O2 C10 C11 -177.4(2) . . . . ?
Ni1 O2 C10 C15 1.3(3) . . . . ?
Ni1 N4 C25 C24 -18.9(3) . . . . ?
Ni1 N4 C25 C26 165.6(2) . . . . ?
Ni1 N4 C31 C30 -161.9(2) . . . . ?
Ni1 N4 C31 C32 20.9(4) . . . . ?
Ni1 N1 C6 C1 -3.4(3) . . . . ?
Ni1 N1 C6 C5 179.1(2) . . . . ?
Ni1 N1 C7 C8 177.2(3) . . . . ?
Ni1 N3 C24 C25 18.9(3) . . . . ?
Ni1 N3 C24 C23 -165.5(2) . . . . ?
Ni1 N3 C20 C21 164.6(2) . . . . ?
Ni1 N3 C20 C19 -17.0(4) . . . . ?
Ni1 N2 C15 C10 4.1(3) . . . . ?
Ni1 N2 C15 C14 -177.6(2) . . . . ?
Ni1 N2 C16 C17 175.0(2) . . . . ?
Cl3 C11 C10 O2 2.6(4) . . . . ?
Cl3 C11 C10 C15 -176.1(2) . . . . ?
Cl3 C11 C12 C13 178.4(3) . . . . ?
Cl1 C2 C3 C4 -173.6(3) . . . . ?
Cl2 C4 C5 C6 174.9(2) . . . . ?
Cl2 C4 C5 C9 -7.9(5) . . . . ?
Cl2 C4 C3 C2 -179.3(3) . . . . ?
O1 C1 C2 Cl1 -5.2(5) . . . . ?
O1 C1 C2 C3 176.6(3) . . . . ?
N4 C25 C24 N3 0.1(4) . . . . ?
N4 C25 C24 C23 -175.7(2) . . . . ?
N4 C25 C26 C27 -179.8(3) . . . . ?
N4 C25 C26 C29 0.3(4) . . . . ?
N4 C31 C30 C29 -2.7(4) . . . . ?
N1 C6 C1 O1 1.3(4) . . . . ?
N1 C6 C1 C2 -176.7(3) . . . . ?
N1 C6 C5 C4 -178.0(3) . . . . ?
N1 C6 C5 C9 4.6(5) . . . . ?
N1 C7 C8 C9 1.3(5) . . . . ?
N3 C24 C23 C22 -2.0(4) . . . . ?
N3 C24 C23 C28 -180.0(3) . . . . ?
N2 C15 C10 O2 -3.8(4) . . . . ?
N2 C15 C10 C11 175.0(3) . . . . ?
N2 C15 C14 C18 2.6(4) . . . . ?
N2 C15 C14 C13 -176.3(3) . . . . ?
N2 C16 C17 C18 0.8(5) . . . . ?
C11 C12 C13 Cl4 179.6(3) . . . . ?
C11 C12 C13 C14 -1.5(5) . . . . ?
C15 N2 C16 C17 -0.4(4) . . . . ?
C15 C14 C13 Cl4 179.5(2) . . . . ?
C15 C14 C13 C12 0.6(5) . . . . ?
C33 C34 C35 C36 0.3(5) . . . . ?
C33 C22 C21 C20 -179.2(3) . . . . ?
C33 C22 C23 C24 -179.7(3) . . . . ?
C33 C22 C23 C28 -1.8(4) . . . . ?
C33 C38 C37 C36 -0.8(5) . . . . ?
C10 C11 C12 C13 -0.2(5) . . . . ?
C10 C15 C14 C18 -179.2(3) . . . . ?
C10 C15 C14 C13 1.9(4) . . . . ?
C18 C14 C13 Cl4 0.7(5) . . . . ?
C18 C14 C13 C12 -178.2(3) . . . . ?
C14 C15 C10 O2 177.9(3) . . . . ?
C14 C15 C10 C11 -3.3(4) . . . . ?
C14 C18 C17 C16 0.6(5) . . . . ?
C34 C33 C22 C21 -53.5(4) . . . . ?
C34 C33 C22 C23 123.4(3) . . . . ?
C34 C33 C38 C37 0.6(5) . . . . ?
C25 N4 C31 C30 3.8(4) . . . . ?
C25 N4 C31 C32 -173.5(3) . . . . ?
C25 C24 C23 C22 173.5(3) . . . . ?
C25 C24 C23 C28 -4.5(4) . . . . ?
C25 C26 C29 C30 0.8(4) . . . . ?
C25 C26 C29 C39 177.8(3) . . . . ?
C31 N4 C25 C24 172.8(2) . . . . ?
C31 N4 C25 C26 -2.7(4) . . . . ?
C31 C30 C29 C39 -176.8(3) . . . . ?
C31 C30 C29 C26 0.3(4) . . . . ?
C24 N3 C20 C21 -4.7(4) . . . . ?
C24 N3 C20 C19 173.8(3) . . . . ?
C24 C25 C26 C27 4.8(4) . . . . ?
C24 C25 C26 C29 -175.0(3) . . . . ?
C24 C23 C28 C27 4.3(4) . . . . ?
C22 C33 C34 C35 177.8(3) . . . . ?
C22 C33 C38 C37 -177.5(3) . . . . ?
C22 C21 C20 N3 0.0(4) . . . . ?
C22 C21 C20 C19 -178.5(3) . . . . ?
C22 C23 C28 C27 -173.6(3) . . . . ?
C12 C11 C10 O2 -178.9(3) . . . . ?
C12 C11 C10 C15 2.4(4) . . . . ?
C21 C22 C23 C24 -2.7(4) . . . . ?
C21 C22 C23 C28 175.2(3) . . . . ?
C38 C33 C34 C35 -0.4(5) . . . . ?
C38 C33 C22 C21 124.6(3) . . . . ?
C38 C33 C22 C23 -58.4(4) . . . . ?
C38 C37 C36 C35 0.7(5) . . . . ?
C23 C22 C21 C20 3.8(4) . . . . ?
C23 C28 C27 C26 0.6(5) . . . . ?
C16 N2 C15 C10 -179.7(3) . . . . ?
C16 N2 C15 C14 -1.3(4) . . . . ?
C4 C5 C9 C8 -178.4(4) . . . . ?
C28 C27 C26 C25 -5.2(5) . . . . ?
C28 C27 C26 C29 174.6(3) . . . . ?
C40 C39 C29 C30 117.4(3) . . . . ?
C40 C39 C29 C26 -59.5(4) . . . . ?
C40 C39 C44 C43 0.2(5) . . . . ?
C40 C41 C42 C43 0.1(6) . . . . ?
C27 C26 C29 C30 -179.0(3) . . . . ?
C27 C26 C29 C39 -2.0(5) . . . . ?
C39 C40 C41 C42 -0.4(5) . . . . ?
C39 C44 C43 C42 -0.5(6) . . . . ?
C26 C25 C24 N3 175.7(3) . . . . ?
C26 C25 C24 C23 -0.1(4) . . . . ?
C37 C36 C35 C34 -0.5(5) . . . . ?
C32 C31 C30 C29 174.5(3) . . . . ?
C6 N1 C7 C8 2.1(5) . . . . ?
C6 C1 C2 Cl1 172.6(2) . . . . ?
C6 C1 C2 C3 -5.6(5) . . . . ?
C6 C5 C9 C8 -1.2(5) . . . . ?
C17 C18 C14 C15 -2.2(5) . . . . ?
C17 C18 C14 C13 176.6(3) . . . . ?
C20 N3 C24 C25 -169.9(2) . . . . ?
C20 N3 C24 C23 5.7(4) . . . . ?
C29 C39 C44 C43 175.2(3) . . . . ?
C1 C6 C5 C4 4.7(5) . . . . ?
C1 C6 C5 C9 -172.8(3) . . . . ?
C1 C2 C3 C4 4.6(5) . . . . ?
C7 N1 C6 C1 172.5(3) . . . . ?
C7 N1 C6 C5 -5.0(4) . . . . ?
C7 C8 C9 C5 -1.6(6) . . . . ?
C44 C39 C29 C30 -57.5(4) . . . . ?
C44 C39 C29 C26 125.6(3) . . . . ?
C5 C4 C3 C2 1.5(5) . . . . ?
C5 C6 C1 O1 178.8(3) . . . . ?
C5 C6 C1 C2 0.8(4) . . . . ?
C41 C40 C39 C29 -174.7(3) . . . . ?
C41 C40 C39 C44 0.3(5) . . . . ?
C41 C42 C43 C44 0.3(6) . . . . ?
C3 C4 C5 C6 -5.8(5) . . . . ?
C3 C4 C5 C9 171.4(4) . . . . ?
