#------------------------------------------------------------------------------
#$Date: 2022-04-12 02:11:16 +0300 (Tue, 12 Apr 2022) $
#$Revision: 274459 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/70/99/7709969.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_7709969
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         'C42 H28 N4 Ni O4, C H4 O'
_chemical_formula_sum            'C43 H32 N4 Ni O5'
_chemical_formula_weight         743.44
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2022-04-02 deposited with the CCDC.	2022-04-11 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 112.069(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   16.869(4)
_cell_length_b                   11.170(2)
_cell_length_c                   20.248(4)
_cell_measurement_reflns_used    8998
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      26.046
_cell_measurement_theta_min      3.028
_cell_volume                     3535.7(13)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298(2)
_diffrn_detector_area_resol_mean 16.0233
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0443
_diffrn_reflns_av_sigmaI/netI    0.0290
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            47087
_diffrn_reflns_theta_full        25.10
_diffrn_reflns_theta_max         25.10
_diffrn_reflns_theta_min         3.03
_exptl_absorpt_coefficient_mu    0.602
_exptl_absorpt_correction_T_max  0.9367
_exptl_absorpt_correction_T_min  0.8640
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0664 before and 0.0560 after correction.
The Ratio of minimum to maximum transmission is 0.9095.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.397
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1544
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.245
_refine_diff_density_min         -0.282
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.995
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     477
_refine_ls_number_reflns         6289
_refine_ls_number_restraints     36
_refine_ls_restrained_S_all      1.001
_refine_ls_R_factor_all          0.0489
_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
'calc w=1/[σ²(Fo²)+(0.0508P)²+1.4062P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0836
_refine_ls_wR_factor_ref         0.0916
_reflns_number_gt                5073
_reflns_number_total             6289
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d2dt00669c2.cif
_cod_data_source_block           Ni10
_cod_original_cell_volume        3535.9(13)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7709969
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Ni1 Ni 0.600829(15) 0.13224(2) 0.358621(13) 0.02731(10) Uani 1 1 d . . .
O1 O 0.59493(9) 0.24489(13) 0.43744(7) 0.0337(3) Uani 1 1 d . . .
N1 N 0.72548(10) 0.19702(15) 0.39590(9) 0.0289(4) Uani 1 1 d . . .
C1 C 0.66634(13) 0.30924(18) 0.46679(11) 0.0322(5) Uani 1 1 d . . .
O2 O 0.77711(10) 0.09317(16) 0.32304(9) 0.0478(4) Uani 1 1 d . . .
H2 H 0.7292 0.0639 0.3111 0.072 Uiso 1 1 calc R . .
N2 N 0.62386(10) -0.01607(15) 0.42549(9) 0.0307(4) Uani 1 1 d . . .
C2 C 0.67657(16) 0.3988(2) 0.51649(11) 0.0406(6) Uani 1 1 d . . .
H2A H 0.6310 0.4188 0.5296 0.049 Uiso 1 1 calc R . .
O3 O 0.62845(9) 0.00711(13) 0.29472(7) 0.0360(3) Uani 1 1 d . . .
N3 N 0.46944(10) 0.09603(15) 0.31339(9) 0.0286(4) Uani 1 1 d . . .
C3 C 0.75431(17) 0.4600(2) 0.54750(12) 0.0472(6) Uani 1 1 d . . .
H3 H 0.7592 0.5191 0.5812 0.057 Uiso 1 1 calc R . .
N4 N 0.55851(10) 0.26432(15) 0.27905(9) 0.0297(4) Uani 1 1 d . . .
O4 O 0.60420(13) 0.07000(15) 0.52103(9) 0.0535(5) Uani 1 1 d . . .
H4 H 0.5989 0.1288 0.4955 0.080 Uiso 1 1 calc R . .
C4 C 0.82295(17) 0.4355(2) 0.52974(13) 0.0486(6) Uani 1 1 d . . .
H4A H 0.8741 0.4766 0.5514 0.058 Uiso 1 1 calc R . .
O5 O 0.53309(17) 0.0213(3) 0.14953(12) 0.1011(8) Uani 1 1 d . . .
H5 H 0.5549 0.0128 0.1929 0.152 Uiso 1 1 calc R . .
C5 C 0.81537(14) 0.3470(2) 0.47808(12) 0.0398(5) Uani 1 1 d . . .
C6 C 0.73744(13) 0.28440(18) 0.44694(10) 0.0303(5) Uani 1 1 d . . .
C7 C 0.78843(13) 0.1726(2) 0.37434(12) 0.0363(5) Uani 1 1 d . . .
C8 C 0.86883(14) 0.2310(2) 0.40330(14) 0.0496(6) Uani 1 1 d . . .
H8 H 0.9124 0.2114 0.3876 0.060 Uiso 1 1 calc R . .
C9 C 0.88142(15) 0.3152(2) 0.45379(14) 0.0511(6) Uani 1 1 d . . .
H9 H 0.9342 0.3532 0.4731 0.061 Uiso 1 1 calc R . .
C10 C 0.64326(13) -0.10246(19) 0.32476(11) 0.0342(5) Uani 1 1 d . . .
C11 C 0.66348(15) -0.2004(2) 0.29301(13) 0.0454(6) Uani 1 1 d . . .
H11 H 0.6660 -0.1926 0.2481 0.055 Uiso 1 1 calc R . .
C12 C 0.68039(16) -0.3117(2) 0.32725(14) 0.0498(6) Uani 1 1 d . . .
H12 H 0.6949 -0.3761 0.3050 0.060 Uiso 1 1 calc R . .
C13 C 0.67610(15) -0.3277(2) 0.39229(14) 0.0460(6) Uani 1 1 d . . .
H13 H 0.6868 -0.4026 0.4139 0.055 Uiso 1 1 calc R . .
C14 C 0.65539(14) -0.2301(2) 0.42695(12) 0.0387(5) Uani 1 1 d . . .
C15 C 0.64077(12) -0.11727(18) 0.39375(11) 0.0307(5) Uani 1 1 d . . .
C16 C 0.62018(15) -0.0254(2) 0.48936(12) 0.0391(5) Uani 1 1 d . . .
C17 C 0.6316(2) -0.1372(2) 0.52525(14) 0.0590(8) Uani 1 1 d . . .
H17 H 0.6272 -0.1422 0.5696 0.071 Uiso 1 1 calc R . .
C18 C 0.64886(18) -0.2360(2) 0.49468(14) 0.0556(7) Uani 1 1 d . . .
H18 H 0.6566 -0.3090 0.5184 0.067 Uiso 1 1 calc R . .
C19 C 0.13893(15) 0.1412(2) 0.20404(14) 0.0460(6) Uani 1 1 d . . .
H19 H 0.1586 0.2145 0.2258 0.055 Uiso 1 1 calc R . .
C20 C 0.05185(16) 0.1221(3) 0.16969(15) 0.0587(7) Uani 1 1 d . . .
H20 H 0.0134 0.1824 0.1687 0.070 Uiso 1 1 calc R . .
C21 C 0.02234(16) 0.0142(3) 0.13715(15) 0.0595(8) Uani 1 1 d . . .
H21 H -0.0361 0.0018 0.1137 0.071 Uiso 1 1 calc R . .
C22 C 0.07875(16) -0.0752(2) 0.13923(13) 0.0518(7) Uani 1 1 d . . .
H22 H 0.0585 -0.1481 0.1171 0.062 Uiso 1 1 calc R . .
C23 C 0.16584(15) -0.0575(2) 0.17417(12) 0.0412(5) Uani 1 1 d . . .
H23 H 0.2037 -0.1192 0.1762 0.049 Uiso 1 1 calc R . .
C24 C 0.19697(13) 0.05177(19) 0.20616(11) 0.0341(5) Uani 1 1 d . . .
C25 C 0.29110(13) 0.07027(18) 0.24251(11) 0.0307(5) Uani 1 1 d . . .
C26 C 0.33875(14) -0.0058(2) 0.29594(12) 0.0377(5) Uani 1 1 d . . .
H26 H 0.3119 -0.0686 0.3095 0.045 Uiso 1 1 calc R . .
C27 C 0.42668(14) 0.00964(19) 0.33017(12) 0.0358(5) Uani 1 1 d . . .
H27 H 0.4567 -0.0431 0.3665 0.043 Uiso 1 1 calc R . .
C28 C 0.42419(12) 0.17197(17) 0.25962(10) 0.0240(4) Uani 1 1 d . . .
C29 C 0.33512(12) 0.16406(17) 0.22298(10) 0.0262(4) Uani 1 1 d . . .
C30 C 0.29456(12) 0.24961(18) 0.16758(10) 0.0291(5) Uani 1 1 d . . .
H30 H 0.2358 0.2451 0.1424 0.035 Uiso 1 1 calc R . .
C31 C 0.33982(13) 0.33653(18) 0.15114(11) 0.0309(5) Uani 1 1 d . . .
H31 H 0.3113 0.3912 0.1155 0.037 Uiso 1 1 calc R . .
C32 C 0.43058(13) 0.34647(17) 0.18731(10) 0.0275(4) Uani 1 1 d . A .
C33 C 0.47238(12) 0.26348(17) 0.24143(10) 0.0254(4) Uani 1 1 d . . .
C34 C 0.60346(13) 0.3486(2) 0.26314(12) 0.0397(6) Uani 1 1 d . . .
H34 H 0.6623 0.3503 0.2883 0.048 Uiso 1 1 calc R . .
C35 C 0.56746(14) 0.4347(2) 0.21086(12) 0.0432(6) Uani 1 1 d . A .
H35 H 0.6023 0.4917 0.2019 0.052 Uiso 1 1 calc R . .
C36 C 0.48102(13) 0.43631(19) 0.17233(11) 0.0342(5) Uani 1 1 d . . .
C37 C 0.44181(13) 0.53473(17) 0.11979(10) 0.0360(7) Uani 0.817(5) 1 d PGU A 2
C38 C 0.44861(17) 0.65244(19) 0.14356(11) 0.0461(8) Uani 0.817(5) 1 d PGU A 2
H38A H 0.4752 0.6692 0.1919 0.055 Uiso 0.817(5) 1 calc PR A 2
C39 C 0.41576(18) 0.74502(17) 0.09506(15) 0.0654(11) Uani 0.817(5) 1 d PGU A 2
H39A H 0.4203 0.8238 0.1110 0.079 Uiso 0.817(5) 1 calc PR A 2
C40 C 0.37610(15) 0.7199(2) 0.02279(14) 0.0716(13) Uani 0.817(5) 1 d PGU A 2
H40A H 0.3541 0.7818 -0.0097 0.086 Uiso 0.817(5) 1 calc PR A 2
C41 C 0.36929(19) 0.6022(3) -0.00098(11) 0.0764(14) Uani 0.817(5) 1 d PGU A 2
H41A H 0.3428 0.5854 -0.0493 0.092 Uiso 0.817(5) 1 calc PR A 2
C42 C 0.40214(19) 0.50960(19) 0.04752(11) 0.0591(11) Uani 0.817(5) 1 d PGU A 2
H42A H 0.3976 0.4309 0.0316 0.071 Uiso 0.817(5) 1 calc PR A 2
C37' C 0.4460(7) 0.5143(10) 0.1082(5) 0.0360(7) Uani 0.183(5) 1 d PG A 1
C38' C 0.4129(8) 0.6220(12) 0.1209(6) 0.0461(8) Uani 0.183(5) 1 d PG A 1
H38B H 0.4132 0.6387 0.1660 0.055 Uiso 0.183(5) 1 calc PR A 1
C39' C 0.3794(8) 0.7048(11) 0.0661(8) 0.0654(11) Uani 0.183(5) 1 d PG A 1
H39B H 0.3573 0.7768 0.0746 0.079 Uiso 0.183(5) 1 calc PR A 1
C40' C 0.3790(8) 0.6798(11) -0.0012(7) 0.0716(13) Uani 0.183(5) 1 d PG A 1
H40B H 0.3566 0.7352 -0.0379 0.086 Uiso 0.183(5) 1 calc PR A 1
C41' C 0.4122(9) 0.5721(11) -0.0139(5) 0.0764(14) Uani 0.183(5) 1 d PG A 1
H41B H 0.4119 0.5555 -0.0590 0.092 Uiso 0.183(5) 1 calc PR A 1
C42' C 0.4457(9) 0.4894(9) 0.0409(6) 0.0591(11) Uani 0.183(5) 1 d PG A 1
H42B H 0.4678 0.4173 0.0324 0.071 Uiso 0.183(5) 1 calc PR A 1
C43 C 0.5814(3) 0.0995(4) 0.1279(2) 0.1089(14) Uani 1 1 d . . .
H43A H 0.5770 0.0790 0.0806 0.163 Uiso 1 1 calc R . .
H43B H 0.6401 0.0945 0.1599 0.163 Uiso 1 1 calc R . .
H43C H 0.5609 0.1796 0.1281 0.163 Uiso 1 1 calc R . .
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'
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 O3 168.84(6) . . ?
O1 Ni1 N1 80.97(6) . . ?
O3 Ni1 N1 91.57(6) . . ?
O1 Ni1 N2 91.93(6) . . ?
O3 Ni1 N2 80.71(6) . . ?
N1 Ni1 N2 97.16(6) . . ?
O1 Ni1 N3 96.04(6) . . ?
O3 Ni1 N3 92.63(6) . . ?
N1 Ni1 N3 170.22(6) . . ?
N2 Ni1 N3 92.23(6) . . ?
O1 Ni1 N4 93.65(6) . . ?
O3 Ni1 N4 94.94(6) . . ?
N1 Ni1 N4 92.28(6) . . ?
N2 Ni1 N4 169.68(6) . . ?
N3 Ni1 N4 78.56(6) . . ?
C1 O1 Ni1 112.01(12) . . ?
C7 N1 C6 118.96(18) . . ?
C7 N1 Ni1 129.65(15) . . ?
C6 N1 Ni1 111.19(12) . . ?
O1 C1 C2 123.9(2) . . ?
O1 C1 C6 118.87(18) . . ?
C2 C1 C6 117.2(2) . . ?
C7 O2 H2 109.5 . . ?
C16 N2 C15 118.94(18) . . ?
C16 N2 Ni1 129.30(15) . . ?
C15 N2 Ni1 111.67(13) . . ?
C1 C2 C3 121.3(2) . . ?
C1 C2 H2A 119.4 . . ?
C3 C2 H2A 119.4 . . ?
C10 O3 Ni1 112.20(12) . . ?
C27 N3 C28 117.55(17) . . ?
C27 N3 Ni1 128.15(14) . . ?
C28 N3 Ni1 114.30(12) . . ?
C4 C3 C2 121.9(2) . . ?
C4 C3 H3 119.0 . . ?
C2 C3 H3 119.0 . . ?
C34 N4 C33 117.19(17) . . ?
C34 N4 Ni1 128.74(14) . . ?
C33 N4 Ni1 114.02(12) . . ?
C16 O4 H4 109.5 . . ?
C3 C4 C5 119.2(2) . . ?
C3 C4 H4A 120.4 . . ?
C5 C4 H4A 120.4 . . ?
C43 O5 H5 109.5 . . ?
C4 C5 C6 119.2(2) . . ?
C4 C5 C9 124.6(2) . . ?
C6 C5 C9 116.2(2) . . ?
N1 C6 C5 122.31(19) . . ?
N1 C6 C1 116.49(18) . . ?
C5 C6 C1 121.2(2) . . ?
N1 C7 O2 120.07(19) . . ?
N1 C7 C8 122.1(2) . . ?
O2 C7 C8 117.8(2) . . ?
C9 C8 C7 119.3(2) . . ?
C9 C8 H8 120.4 . . ?
C7 C8 H8 120.4 . . ?
C8 C9 C5 121.1(2) . . ?
C8 C9 H9 119.4 . . ?
C5 C9 H9 119.4 . . ?
O3 C10 C11 123.2(2) . . ?
O3 C10 C15 118.67(18) . . ?
C11 C10 C15 118.1(2) . . ?
C10 C11 C12 121.0(2) . . ?
C10 C11 H11 119.5 . . ?
C12 C11 H11 119.5 . . ?
C13 C12 C11 121.5(2) . . ?
C13 C12 H12 119.3 . . ?
C11 C12 H12 119.3 . . ?
C12 C13 C14 119.6(2) . . ?
C12 C13 H13 120.2 . . ?
C14 C13 H13 120.2 . . ?
C15 C14 C13 119.1(2) . . ?
C15 C14 C18 116.1(2) . . ?
C13 C14 C18 124.7(2) . . ?
N2 C15 C14 122.74(19) . . ?
N2 C15 C10 116.67(18) . . ?
C14 C15 C10 120.6(2) . . ?
N2 C16 O4 120.23(19) . . ?
N2 C16 C17 121.5(2) . . ?
O4 C16 C17 118.3(2) . . ?
C18 C17 C16 119.7(2) . . ?
C18 C17 H17 120.1 . . ?
C16 C17 H17 120.1 . . ?
C17 C18 C14 120.9(2) . . ?
C17 C18 H18 119.5 . . ?
C14 C18 H18 119.5 . . ?
C20 C19 C24 120.5(2) . . ?
C20 C19 H19 119.8 . . ?
C24 C19 H19 119.8 . . ?
C21 C20 C19 120.0(3) . . ?
C21 C20 H20 120.0 . . ?
C19 C20 H20 120.0 . . ?
C22 C21 C20 120.2(2) . . ?
C22 C21 H21 119.9 . . ?
C20 C21 H21 119.9 . . ?
C21 C22 C23 120.2(2) . . ?
C21 C22 H22 119.9 . . ?
C23 C22 H22 119.9 . . ?
C22 C23 C24 120.4(2) . . ?
C22 C23 H23 119.8 . . ?
C24 C23 H23 119.8 . . ?
C19 C24 C23 118.7(2) . . ?
C19 C24 C25 121.5(2) . . ?
C23 C24 C25 119.8(2) . . ?
C26 C25 C29 117.53(18) . . ?
C26 C25 C24 120.16(18) . . ?
C29 C25 C24 122.30(18) . . ?
C25 C26 C27 120.97(19) . . ?
C25 C26 H26 119.5 . . ?
C27 C26 H26 119.5 . . ?
N3 C27 C26 122.97(19) . . ?
N3 C27 H27 118.5 . . ?
C26 C27 H27 118.5 . . ?
N3 C28 C29 123.24(17) . . ?
N3 C28 C33 116.47(17) . . ?
C29 C28 C33 120.29(17) . . ?
C28 C29 C25 117.72(18) . . ?
C28 C29 C30 118.10(17) . . ?
C25 C29 C30 124.17(18) . . ?
C31 C30 C29 121.53(18) . . ?
C31 C30 H30 119.2 . . ?
C29 C30 H30 119.2 . . ?
C30 C31 C32 121.61(19) . . ?
C30 C31 H31 119.2 . . ?
C32 C31 H31 119.2 . . ?
C33 C32 C36 117.85(18) . . ?
C33 C32 C31 118.31(17) . . ?
C36 C32 C31 123.84(18) . . ?
N4 C33 C32 123.22(17) . . ?
N4 C33 C28 116.63(17) . . ?
C32 C33 C28 120.15(17) . . ?
N4 C34 C35 123.49(19) . . ?
N4 C34 H34 118.3 . . ?
C35 C34 H34 118.3 . . ?
C36 C35 C34 120.6(2) . . ?
C36 C35 H35 119.7 . . ?
C34 C35 H35 119.7 . . ?
C35 C36 C32 117.60(19) . . ?
C35 C36 C37' 119.5(5) . . ?
C32 C36 C37' 121.8(5) . . ?
C35 C36 C37 120.31(19) . . ?
C32 C36 C37 121.97(18) . . ?
C37' C36 C37 13.6(5) . . ?
C38 C37 C42 120.0 . . ?
C38 C37 C36 119.39(15) . . ?
C42 C37 C36 120.55(15) . . ?
C37 C38 C39 120.0 . . ?
C37 C38 H38A 120.0 . . ?
C39 C38 H38A 120.0 . . ?
C40 C39 C38 120.0 . . ?
C40 C39 H39A 120.0 . . ?
C38 C39 H39A 120.0 . . ?
C39 C40 C41 120.0 . . ?
C39 C40 H40A 120.0 . . ?
C41 C40 H40A 120.0 . . ?
C42 C41 C40 120.0 . . ?
C42 C41 H41A 120.0 . . ?
C40 C41 H41A 120.0 . . ?
C41 C42 C37 120.0 . . ?
C41 C42 H42A 120.0 . . ?
C37 C42 H42A 120.0 . . ?
C38' C37' C42' 120.0 . . ?
C38' C37' C36 113.7(8) . . ?
C42' C37' C36 126.3(8) . . ?
C37' C38' C39' 120.0 . . ?
C37' C38' H38B 120.0 . . ?
C39' C38' H38B 120.0 . . ?
C40' C39' C38' 120.0 . . ?
C40' C39' H39B 120.0 . . ?
C38' C39' H39B 120.0 . . ?
C39' C40' C41' 120.0 . . ?
C39' C40' H40B 120.0 . . ?
C41' C40' H40B 120.0 . . ?
C42' C41' C40' 120.0 . . ?
C42' C41' H41B 120.0 . . ?
C40' C41' H41B 120.0 . . ?
C41' C42' C37' 120.0 . . ?
C41' C42' H42B 120.0 . . ?
C37' C42' H42B 120.0 . . ?
O5 C43 H43A 109.5 . . ?
O5 C43 H43B 109.5 . . ?
H43A C43 H43B 109.5 . . ?
O5 C43 H43C 109.5 . . ?
H43A C43 H43C 109.5 . . ?
H43B C43 H43C 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 2.0639(14) . ?
Ni1 O3 2.0731(15) . ?
Ni1 N1 2.0790(17) . ?
Ni1 N2 2.0817(17) . ?
Ni1 N3 2.0951(17) . ?
Ni1 N4 2.1018(17) . ?
O1 C1 1.335(3) . ?
N1 C7 1.319(3) . ?
N1 C6 1.380(3) . ?
C1 C2 1.383(3) . ?
C1 C6 1.428(3) . ?
O2 C7 1.325(3) . ?
O2 H2 0.8200 . ?
N2 C16 1.322(3) . ?
N2 C15 1.382(3) . ?
C2 C3 1.401(3) . ?
C2 H2A 0.9300 . ?
O3 C10 1.348(3) . ?
N3 C27 1.323(3) . ?
N3 C28 1.365(2) . ?
C3 C4 1.363(4) . ?
C3 H3 0.9300 . ?
N4 C34 1.322(3) . ?
N4 C33 1.364(2) . ?
O4 C16 1.323(3) . ?
O4 H4 0.8200 . ?
C4 C5 1.410(3) . ?
C4 H4A 0.9300 . ?
O5 C43 1.374(4) . ?
O5 H5 0.8200 . ?
C5 C6 1.411(3) . ?
C5 C9 1.422(3) . ?
C7 C8 1.418(3) . ?
C8 C9 1.345(4) . ?
C8 H8 0.9300 . ?
C9 H9 0.9300 . ?
C10 C11 1.375(3) . ?
C10 C15 1.423(3) . ?
C11 C12 1.399(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.358(4) . ?
C12 H12 0.9300 . ?
C13 C14 1.409(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.406(3) . ?
C14 C18 1.418(3) . ?
C16 C17 1.420(3) . ?
C17 C18 1.350(4) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C19 C20 1.385(3) . ?
C19 C24 1.388(3) . ?
C19 H19 0.9300 . ?
C20 C21 1.374(4) . ?
C20 H20 0.9300 . ?
C21 C22 1.369(4) . ?
C21 H21 0.9300 . ?
C22 C23 1.385(3) . ?
C22 H22 0.9300 . ?
C23 C24 1.389(3) . ?
C23 H23 0.9300 . ?
C24 C25 1.493(3) . ?
C25 C26 1.373(3) . ?
C25 C29 1.423(3) . ?
C26 C27 1.392(3) . ?
C26 H26 0.9300 . ?
C27 H27 0.9300 . ?
C28 C29 1.407(3) . ?
C28 C33 1.437(3) . ?
C29 C30 1.436(3) . ?
C30 C31 1.352(3) . ?
C30 H30 0.9300 . ?
C31 C32 1.432(3) . ?
C31 H31 0.9300 . ?
C32 C33 1.406(3) . ?
C32 C36 1.420(3) . ?
C34 C35 1.390(3) . ?
C34 H34 0.9300 . ?
C35 C36 1.371(3) . ?
C35 H35 0.9300 . ?
C36 C37' 1.488(9) . ?
C36 C37 1.500(3) . ?
C37 C38 1.3900 . ?
C37 C42 1.3900 . ?
C38 C39 1.3900 . ?
C38 H38A 0.9300 . ?
C39 C40 1.3900 . ?
C39 H39A 0.9300 . ?
C40 C41 1.3900 . ?
C40 H40A 0.9300 . ?
C41 C42 1.3900 . ?
C41 H41A 0.9300 . ?
C42 H42A 0.9300 . ?
C37' C38' 1.3900 . ?
C37' C42' 1.3900 . ?
C38' C39' 1.3900 . ?
C38' H38B 0.9300 . ?
C39' C40' 1.3900 . ?
C39' H39B 0.9300 . ?
C40' C41' 1.3900 . ?
C40' H40B 0.9300 . ?
C41' C42' 1.3900 . ?
C41' H41B 0.9300 . ?
C42' H42B 0.9300 . ?
C43 H43A 0.9600 . ?
C43 H43B 0.9600 . ?
C43 H43C 0.9600 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O2 H2 O3 0.82 1.73 2.542(2) 173.9 .
O4 H4 O1 0.82 1.73 2.551(2) 173.6 .
O5 H5 O3 0.82 1.97 2.775(3) 168.0 .
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
O3 Ni1 O1 C1 54.7(3) . . . . ?
N1 Ni1 O1 C1 6.12(13) . . . . ?
N2 Ni1 O1 C1 103.07(13) . . . . ?
N3 Ni1 O1 C1 -164.48(13) . . . . ?
N4 Ni1 O1 C1 -85.61(13) . . . . ?
O1 Ni1 N1 C7 -179.58(19) . . . . ?
O3 Ni1 N1 C7 8.77(18) . . . . ?
N2 Ni1 N1 C7 89.60(19) . . . . ?
N3 Ni1 N1 C7 -106.7(4) . . . . ?
N4 Ni1 N1 C7 -86.24(19) . . . . ?
O1 Ni1 N1 C6 -4.86(12) . . . . ?
O3 Ni1 N1 C6 -176.51(13) . . . . ?
N2 Ni1 N1 C6 -95.68(13) . . . . ?
N3 Ni1 N1 C6 68.1(4) . . . . ?
N4 Ni1 N1 C6 88.47(13) . . . . ?
Ni1 O1 C1 C2 174.24(16) . . . . ?
Ni1 O1 C1 C6 -6.5(2) . . . . ?
O1 Ni1 N2 C16 9.32(19) . . . . ?
O3 Ni1 N2 C16 -179.1(2) . . . . ?
N1 Ni1 N2 C16 90.47(19) . . . . ?
N3 Ni1 N2 C16 -86.80(19) . . . . ?
N4 Ni1 N2 C16 -113.4(4) . . . . ?
O1 Ni1 N2 C15 -174.26(13) . . . . ?
O3 Ni1 N2 C15 -2.69(13) . . . . ?
N1 Ni1 N2 C15 -93.12(14) . . . . ?
N3 Ni1 N2 C15 89.61(14) . . . . ?
N4 Ni1 N2 C15 63.0(4) . . . . ?
O1 C1 C2 C3 177.42(19) . . . . ?
C6 C1 C2 C3 -1.8(3) . . . . ?
O1 Ni1 O3 C10 51.6(3) . . . . ?
N1 Ni1 O3 C10 99.40(13) . . . . ?
N2 Ni1 O3 C10 2.40(13) . . . . ?
N3 Ni1 O3 C10 -89.44(13) . . . . ?
N4 Ni1 O3 C10 -168.17(13) . . . . ?
O1 Ni1 N3 C27 -89.39(18) . . . . ?
O3 Ni1 N3 C27 83.59(18) . . . . ?
N1 Ni1 N3 C27 -161.1(3) . . . . ?
N2 Ni1 N3 C27 2.79(18) . . . . ?
N4 Ni1 N3 C27 178.10(19) . . . . ?
O1 Ni1 N3 C28 91.23(14) . . . . ?
O3 Ni1 N3 C28 -95.79(14) . . . . ?
N1 Ni1 N3 C28 19.6(5) . . . . ?
N2 Ni1 N3 C28 -176.59(14) . . . . ?
N4 Ni1 N3 C28 -1.28(13) . . . . ?
C1 C2 C3 C4 0.8(3) . . . . ?
O1 Ni1 N4 C34 83.60(19) . . . . ?
O3 Ni1 N4 C34 -89.27(19) . . . . ?
N1 Ni1 N4 C34 2.5(2) . . . . ?
N2 Ni1 N4 C34 -153.8(3) . . . . ?
N3 Ni1 N4 C34 179.0(2) . . . . ?
O1 Ni1 N4 C33 -93.74(14) . . . . ?
O3 Ni1 N4 C33 93.39(14) . . . . ?
N1 Ni1 N4 C33 -174.83(14) . . . . ?
N2 Ni1 N4 C33 28.8(4) . . . . ?
N3 Ni1 N4 C33 1.70(13) . . . . ?
C2 C3 C4 C5 0.7(4) . . . . ?
C3 C4 C5 C6 -1.1(3) . . . . ?
C3 C4 C5 C9 178.4(2) . . . . ?
C7 N1 C6 C5 -1.4(3) . . . . ?
Ni1 N1 C6 C5 -176.75(16) . . . . ?
C7 N1 C6 C1 178.34(18) . . . . ?
Ni1 N1 C6 C1 3.0(2) . . . . ?
C4 C5 C6 N1 179.74(19) . . . . ?
C9 C5 C6 N1 0.1(3) . . . . ?
C4 C5 C6 C1 0.0(3) . . . . ?
C9 C5 C6 C1 -179.6(2) . . . . ?
O1 C1 C6 N1 2.4(3) . . . . ?
C2 C1 C6 N1 -178.30(17) . . . . ?
O1 C1 C6 C5 -177.87(18) . . . . ?
C2 C1 C6 C5 1.4(3) . . . . ?
C6 N1 C7 O2 -176.84(18) . . . . ?
Ni1 N1 C7 O2 -2.5(3) . . . . ?
C6 N1 C7 C8 1.7(3) . . . . ?
Ni1 N1 C7 C8 176.12(17) . . . . ?
N1 C7 C8 C9 -0.8(4) . . . . ?
O2 C7 C8 C9 177.8(2) . . . . ?
C7 C8 C9 C5 -0.5(4) . . . . ?
C4 C5 C9 C8 -178.8(2) . . . . ?
C6 C5 C9 C8 0.8(4) . . . . ?
Ni1 O3 C10 C11 -179.56(17) . . . . ?
Ni1 O3 C10 C15 -1.7(2) . . . . ?
O3 C10 C11 C12 178.4(2) . . . . ?
C15 C10 C11 C12 0.6(3) . . . . ?
C10 C11 C12 C13 1.1(4) . . . . ?
C11 C12 C13 C14 -0.9(4) . . . . ?
C12 C13 C14 C15 -0.9(3) . . . . ?
C12 C13 C14 C18 179.9(2) . . . . ?
C16 N2 C15 C14 -0.8(3) . . . . ?
Ni1 N2 C15 C14 -177.66(16) . . . . ?
C16 N2 C15 C10 179.45(19) . . . . ?
Ni1 N2 C15 C10 2.6(2) . . . . ?
C13 C14 C15 N2 -177.1(2) . . . . ?
C18 C14 C15 N2 2.2(3) . . . . ?
C13 C14 C15 C10 2.6(3) . . . . ?
C18 C14 C15 C10 -178.1(2) . . . . ?
O3 C10 C15 N2 -0.6(3) . . . . ?
C11 C10 C15 N2 177.31(19) . . . . ?
O3 C10 C15 C14 179.66(18) . . . . ?
C11 C10 C15 C14 -2.4(3) . . . . ?
C15 N2 C16 O4 179.93(19) . . . . ?
Ni1 N2 C16 O4 -3.9(3) . . . . ?
C15 N2 C16 C17 -1.2(3) . . . . ?
Ni1 N2 C16 C17 175.01(19) . . . . ?
N2 C16 C17 C18 1.8(4) . . . . ?
O4 C16 C17 C18 -179.3(3) . . . . ?
C16 C17 C18 C14 -0.3(4) . . . . ?
C15 C14 C18 C17 -1.6(4) . . . . ?
C13 C14 C18 C17 177.7(3) . . . . ?
C24 C19 C20 C21 -0.3(4) . . . . ?
C19 C20 C21 C22 0.7(4) . . . . ?
C20 C21 C22 C23 0.1(4) . . . . ?
C21 C22 C23 C24 -1.3(4) . . . . ?
C20 C19 C24 C23 -1.0(4) . . . . ?
C20 C19 C24 C25 179.7(2) . . . . ?
C22 C23 C24 C19 1.8(3) . . . . ?
C22 C23 C24 C25 -178.9(2) . . . . ?
C19 C24 C25 C26 123.3(2) . . . . ?
C23 C24 C25 C26 -56.0(3) . . . . ?
C19 C24 C25 C29 -58.0(3) . . . . ?
C23 C24 C25 C29 122.7(2) . . . . ?
C29 C25 C26 C27 0.8(3) . . . . ?
C24 C25 C26 C27 179.6(2) . . . . ?
C28 N3 C27 C26 -0.4(3) . . . . ?
Ni1 N3 C27 C26 -179.81(16) . . . . ?
C25 C26 C27 N3 -0.7(3) . . . . ?
C27 N3 C28 C29 1.5(3) . . . . ?
Ni1 N3 C28 C29 -179.07(15) . . . . ?
C27 N3 C28 C33 -178.75(18) . . . . ?
Ni1 N3 C28 C33 0.7(2) . . . . ?
N3 C28 C29 C25 -1.3(3) . . . . ?
C33 C28 C29 C25 178.90(17) . . . . ?
N3 C28 C29 C30 179.66(18) . . . . ?
C33 C28 C29 C30 -0.1(3) . . . . ?
C26 C25 C29 C28 0.1(3) . . . . ?
C24 C25 C29 C28 -178.64(18) . . . . ?
C26 C25 C29 C30 179.08(19) . . . . ?
C24 C25 C29 C30 0.3(3) . . . . ?
C28 C29 C30 C31 -0.7(3) . . . . ?
C25 C29 C30 C31 -179.67(19) . . . . ?
C29 C30 C31 C32 1.0(3) . . . . ?
C30 C31 C32 C33 -0.5(3) . . . . ?
C30 C31 C32 C36 -179.7(2) . . . . ?
C34 N4 C33 C32 0.4(3) . . . . ?
Ni1 N4 C33 C32 178.05(15) . . . . ?
C34 N4 C33 C28 -179.55(19) . . . . ?
Ni1 N4 C33 C28 -1.9(2) . . . . ?
C36 C32 C33 N4 -1.0(3) . . . . ?
C31 C32 C33 N4 179.70(18) . . . . ?
C36 C32 C33 C28 178.92(18) . . . . ?
C31 C32 C33 C28 -0.4(3) . . . . ?
N3 C28 C33 N4 0.8(3) . . . . ?
C29 C28 C33 N4 -179.43(17) . . . . ?
N3 C28 C33 C32 -179.14(17) . . . . ?
C29 C28 C33 C32 0.6(3) . . . . ?
C33 N4 C34 C35 0.1(3) . . . . ?
Ni1 N4 C34 C35 -177.19(18) . . . . ?
N4 C34 C35 C36 0.1(4) . . . . ?
C34 C35 C36 C32 -0.8(3) . . . . ?
C34 C35 C36 C37' -168.9(6) . . . . ?
C34 C35 C36 C37 175.5(2) . . . . ?
C33 C32 C36 C35 1.2(3) . . . . ?
C31 C32 C36 C35 -179.6(2) . . . . ?
C33 C32 C36 C37' 169.0(6) . . . . ?
C31 C32 C36 C37' -11.8(7) . . . . ?
C33 C32 C36 C37 -175.04(19) . . . . ?
C31 C32 C36 C37 4.2(3) . . . . ?
C35 C36 C37 C38 -61.1(3) . . . . ?
C32 C36 C37 C38 115.0(2) . . . . ?
C37' C36 C37 C38 -152(2) . . . . ?
C35 C36 C37 C42 116.2(2) . . . . ?
C32 C36 C37 C42 -67.7(3) . . . . ?
C37' C36 C37 C42 26(2) . . . . ?
C42 C37 C38 C39 0.0 . . . . ?
C36 C37 C38 C39 177.3(2) . . . . ?
C37 C38 C39 C40 0.0 . . . . ?
C38 C39 C40 C41 0.0 . . . . ?
C39 C40 C41 C42 0.0 . . . . ?
C40 C41 C42 C37 0.0 . . . . ?
C38 C37 C42 C41 0.0 . . . . ?
C36 C37 C42 C41 -177.2(2) . . . . ?
C35 C36 C37' C38' -99.0(8) . . . . ?
C32 C36 C37' C38' 93.4(7) . . . . ?
C37 C36 C37' C38' -1.6(16) . . . . ?
C35 C36 C37' C42' 79.8(9) . . . . ?
C32 C36 C37' C42' -87.8(8) . . . . ?
C37 C36 C37' C42' 177(3) . . . . ?
C42' C37' C38' C39' 0.0 . . . . ?
C36 C37' C38' C39' 178.9(9) . . . . ?
C37' C38' C39' C40' 0.0 . . . . ?
C38' C39' C40' C41' 0.0 . . . . ?
C39' C40' C41' C42' 0.0 . . . . ?
C40' C41' C42' C37' 0.0 . . . . ?
C38' C37' C42' C41' 0.0 . . . . ?
C36 C37' C42' C41' -178.7(10) . . . . ?
