#------------------------------------------------------------------------------
#$Date: 2021-07-18 04:36:16 +0300 (Sun, 18 Jul 2021) $
#$Revision: 267626 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/42/1564206.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_1564206
loop_
_publ_author_name
'Beagan, Daniel M.'
'Cabelof, Alyssa C.'
'Pink, Maren'
'Carta, Veronica'
'Gao, Xinfeng'
'Caulton, Kenneth G.'
_publ_section_title
;
 Nickel-mediated N--N bond formation and N2O liberation via nitrogen
 oxyanion reduction
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D1SC02846D
_journal_year                    2021
_chemical_formula_moiety         'C22 H28 N4 Ni O3'
_chemical_formula_sum            'C22 H28 N4 Ni O3'
_chemical_formula_weight         455.19
_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-2018/3
_audit_update_record
;
2021-05-11 deposited with the CCDC.	2021-07-13 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 111.731(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.6060(7)
_cell_length_b                   16.8019(11)
_cell_length_c                   12.3281(8)
_cell_measurement_reflns_used    9006
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.17
_cell_measurement_theta_min      3.01
_cell_volume                     2233.2(2)
_computing_cell_refinement       'SAINT V8.38A (BrukerNano, 2017)'
_computing_data_collection       'BIS v6.2.9 (BrukerNano, 2018)'
_computing_data_reduction        'SAINT V8.38A (BrukerNano, 2017)'
_computing_publication_material  'APEX3 v2018.1-0 (BrukerNano, 2018)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_structure_solution    'XT, VERSION 2014/5'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 7.3910
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
'0.50 degree frames measured for 2 seconds each'
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'multilayer mirror'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0745
_diffrn_reflns_av_unetI/netI     0.0418
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            51982
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.316
_diffrn_reflns_theta_min         2.060
_diffrn_source                   'microfocus sealed tube'
_diffrn_source_type              'Incoatec I\mS 3.0'
_exptl_absorpt_coefficient_mu    0.899
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6718
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, G. Sheldrick; 2018'
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.354
_exptl_crystal_description       block
_exptl_crystal_F_000             960
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.110
_refine_diff_density_max         0.456
_refine_diff_density_min         -0.513
_refine_diff_density_rms         0.088
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.114
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     279
_refine_ls_number_reflns         5558
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.114
_refine_ls_R_factor_all          0.0602
_refine_ls_R_factor_gt           0.0430
_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)+(0.0348P)²+3.2020P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0969
_refine_ls_wR_factor_ref         0.1086
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4368
_reflns_number_total             5558
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1sc02846d3.cif
_cod_data_source_block           20009
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               1564206
_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   0.807
_shelx_estimated_absorpt_t_max   0.908
loop_
_space_group_symop_operation_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_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 0.76472(3) 0.71244(2) 0.57350(3) 0.01404(9) Uani 1 1 d . . . . .
O1 O 0.92694(18) 0.83132(12) 0.55499(18) 0.0290(4) Uani 1 1 d . . . . .
O2 O 0.81564(18) 0.60916(11) 0.65754(16) 0.0253(4) Uani 1 1 d . . . . .
O3 O 0.9250(2) 0.67730(12) 0.80402(17) 0.0314(5) Uani 1 1 d . . . . .
N1 N 0.60565(18) 0.72989(11) 0.60138(17) 0.0141(4) Uani 1 1 d . . . . .
N2 N 0.64319(18) 0.65975(11) 0.43081(16) 0.0127(4) Uani 1 1 d . . . . .
N3 N 0.86130(19) 0.78177(12) 0.56744(18) 0.0177(4) Uani 1 1 d . . . . .
N4 N 0.8933(2) 0.61060(13) 0.7632(2) 0.0245(5) Uani 1 1 d . . . . .
C1 C 0.5922(2) 0.77079(13) 0.6987(2) 0.0137(4) Uani 1 1 d . . . . .
C2 C 0.5806(2) 0.72622(14) 0.7898(2) 0.0149(5) Uani 1 1 d . . . . .
C3 C 0.5611(2) 0.76730(14) 0.8800(2) 0.0163(5) Uani 1 1 d . . . . .
H3 H 0.551436 0.737842 0.941827 0.020 Uiso 1 1 calc R U . . .
C4 C 0.5555(2) 0.84975(14) 0.8822(2) 0.0163(5) Uani 1 1 d . . . . .
C5 C 0.5725(2) 0.89230(14) 0.7921(2) 0.0167(5) Uani 1 1 d . . . . .
H5 H 0.572194 0.948809 0.794335 0.020 Uiso 1 1 calc R U . . .
C6 C 0.5899(2) 0.85424(14) 0.6986(2) 0.0144(4) Uani 1 1 d . . . . .
C7 C 0.5863(2) 0.63667(14) 0.7912(2) 0.0208(5) Uani 1 1 d . . . . .
H7A H 0.508445 0.615286 0.735132 0.031 Uiso 1 1 calc R U . . .
H7B H 0.598480 0.617274 0.869686 0.031 Uiso 1 1 calc R U . . .
H7C H 0.655534 0.619171 0.769761 0.031 Uiso 1 1 calc R U . . .
C8 C 0.5279(2) 0.89249(16) 0.9769(2) 0.0222(5) Uani 1 1 d . . . . .
H8A H 0.439375 0.905614 0.949146 0.033 Uiso 1 1 calc R U . . .
H8B H 0.576827 0.941572 0.997537 0.033 Uiso 1 1 calc R U . . .
H8C H 0.549407 0.858166 1.045895 0.033 Uiso 1 1 calc R U . . .
C9 C 0.6042(2) 0.90141(15) 0.6007(2) 0.0200(5) Uani 1 1 d . . . . .
H9A H 0.684127 0.888768 0.594872 0.030 Uiso 1 1 calc R U . . .
H9B H 0.600862 0.958380 0.616324 0.030 Uiso 1 1 calc R U . . .
H9C H 0.536887 0.887823 0.527138 0.030 Uiso 1 1 calc R U . . .
C10 C 0.5072(2) 0.70870(13) 0.5163(2) 0.0138(4) Uani 1 1 d . . . . .
C11 C 0.5284(2) 0.66387(13) 0.42031(19) 0.0131(4) Uani 1 1 d . . . . .
C12 C 0.3783(2) 0.72714(14) 0.5076(2) 0.0172(5) Uani 1 1 d . . . . .
H12A H 0.374708 0.726333 0.585774 0.026 Uiso 1 1 calc R U . . .
H12B H 0.321140 0.687189 0.458426 0.026 Uiso 1 1 calc R U . . .
H12C H 0.354426 0.779986 0.472924 0.026 Uiso 1 1 calc R U . . .
C13 C 0.4214(2) 0.62857(14) 0.3238(2) 0.0165(5) Uani 1 1 d . . . . .
H13A H 0.451208 0.601878 0.268459 0.025 Uiso 1 1 calc R U . . .
H13B H 0.363012 0.670788 0.283344 0.025 Uiso 1 1 calc R U . . .
H13C H 0.379488 0.589821 0.355919 0.025 Uiso 1 1 calc R U . . .
C14 C 0.6770(2) 0.61737(14) 0.3461(2) 0.0132(4) Uani 1 1 d . . . . .
C15 C 0.7065(2) 0.66090(14) 0.2632(2) 0.0152(5) Uani 1 1 d . . . . .
C16 C 0.7416(2) 0.61862(15) 0.1835(2) 0.0196(5) Uani 1 1 d . . . . .
H16 H 0.760339 0.647186 0.125575 0.024 Uiso 1 1 calc R U . . .
C17 C 0.7504(2) 0.53612(15) 0.1855(2) 0.0196(5) Uani 1 1 d . . . . .
C18 C 0.7218(2) 0.49516(15) 0.2698(2) 0.0189(5) Uani 1 1 d . . . . .
H18 H 0.727227 0.438730 0.271966 0.023 Uiso 1 1 calc R U . . .
C19 C 0.6852(2) 0.53438(14) 0.3518(2) 0.0153(5) Uani 1 1 d . . . . .
C20 C 0.6984(3) 0.75061(15) 0.2584(2) 0.0219(5) Uani 1 1 d . . . . .
H20A H 0.616550 0.767346 0.255828 0.033 Uiso 1 1 calc R U . . .
H20B H 0.710769 0.769686 0.188411 0.033 Uiso 1 1 calc R U . . .
H20C H 0.762718 0.773007 0.328037 0.033 Uiso 1 1 calc R U . . .
C21 C 0.7897(3) 0.49217(18) 0.0980(3) 0.0297(6) Uani 1 1 d . . . . .
H21A H 0.718529 0.463323 0.043237 0.045 Uiso 1 1 calc R U . . .
H21B H 0.855690 0.454314 0.139135 0.045 Uiso 1 1 calc R U . . .
H21C H 0.820440 0.530344 0.054990 0.045 Uiso 1 1 calc R U . . .
C22 C 0.6568(2) 0.48859(14) 0.4436(2) 0.0202(5) Uani 1 1 d . . . . .
H22A H 0.683625 0.433246 0.444159 0.030 Uiso 1 1 calc R U . . .
H22B H 0.567270 0.490022 0.426169 0.030 Uiso 1 1 calc R U . . .
H22C H 0.700823 0.512648 0.520253 0.030 Uiso 1 1 calc R U . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N3 Ni1 O2 124.50(9) . . ?
N3 Ni1 N2 122.99(9) . . ?
O2 Ni1 N2 92.78(8) . . ?
N3 Ni1 N1 126.05(9) . . ?
O2 Ni1 N1 98.71(8) . . ?
N2 Ni1 N1 79.82(8) . . ?
N4 O2 Ni1 118.25(16) . . ?
C10 N1 C1 118.40(19) . . ?
C10 N1 Ni1 114.43(15) . . ?
C1 N1 Ni1 126.76(15) . . ?
C11 N2 C14 120.27(19) . . ?
C11 N2 Ni1 115.35(15) . . ?
C14 N2 Ni1 124.34(15) . . ?
O1 N3 Ni1 175.5(2) . . ?
O3 N4 O2 115.2(2) . . ?
C2 C1 C6 122.0(2) . . ?
C2 C1 N1 119.1(2) . . ?
C6 C1 N1 118.9(2) . . ?
C3 C2 C1 117.9(2) . . ?
C3 C2 C7 120.3(2) . . ?
C1 C2 C7 121.9(2) . . ?
C4 C3 C2 122.2(2) . . ?
C4 C3 H3 118.9 . . ?
C2 C3 H3 118.9 . . ?
C3 C4 C5 118.3(2) . . ?
C3 C4 C8 121.2(2) . . ?
C5 C4 C8 120.5(2) . . ?
C4 C5 C6 121.9(2) . . ?
C4 C5 H5 119.0 . . ?
C6 C5 H5 119.0 . . ?
C5 C6 C1 117.7(2) . . ?
C5 C6 C9 120.9(2) . . ?
C1 C6 C9 121.4(2) . . ?
C2 C7 H7A 109.5 . . ?
C2 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C2 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C4 C8 H8A 109.5 . . ?
C4 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C4 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C6 C9 H9A 109.5 . . ?
C6 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C6 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N1 C10 C12 124.5(2) . . ?
N1 C10 C11 115.4(2) . . ?
C12 C10 C11 120.1(2) . . ?
N2 C11 C13 125.7(2) . . ?
N2 C11 C10 114.4(2) . . ?
C13 C11 C10 120.0(2) . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C19 C14 C15 121.9(2) . . ?
C19 C14 N2 119.4(2) . . ?
C15 C14 N2 118.7(2) . . ?
C16 C15 C14 117.7(2) . . ?
C16 C15 C20 120.9(2) . . ?
C14 C15 C20 121.4(2) . . ?
C17 C16 C15 122.4(2) . . ?
C17 C16 H16 118.8 . . ?
C15 C16 H16 118.8 . . ?
C18 C17 C16 118.2(2) . . ?
C18 C17 C21 120.8(2) . . ?
C16 C17 C21 121.0(2) . . ?
C17 C18 C19 122.0(2) . . ?
C17 C18 H18 119.0 . . ?
C19 C18 H18 119.0 . . ?
C14 C19 C18 117.9(2) . . ?
C14 C19 C22 121.3(2) . . ?
C18 C19 C22 120.9(2) . . ?
C15 C20 H20A 109.5 . . ?
C15 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C15 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C17 C21 H21A 109.5 . . ?
C17 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C17 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C19 C22 H22A 109.5 . . ?
C19 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C19 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 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 N3 1.637(2) . ?
Ni1 O2 1.9952(19) . ?
Ni1 N2 2.0075(19) . ?
Ni1 N1 2.0204(19) . ?
O1 N3 1.176(3) . ?
O2 N4 1.280(3) . ?
O3 N4 1.228(3) . ?
N1 C10 1.282(3) . ?
N1 C1 1.441(3) . ?
N2 C11 1.291(3) . ?
N2 C14 1.434(3) . ?
C1 C2 1.397(3) . ?
C1 C6 1.402(3) . ?
C2 C3 1.396(3) . ?
C2 C7 1.506(3) . ?
C3 C4 1.388(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.396(3) . ?
C4 C8 1.503(3) . ?
C5 C6 1.397(3) . ?
C5 H5 0.9500 . ?
C6 C9 1.503(3) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 C12 1.493(3) . ?
C10 C11 1.498(3) . ?
C11 C13 1.489(3) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 C19 1.398(3) . ?
C14 C15 1.399(3) . ?
C15 C16 1.390(3) . ?
C15 C20 1.510(3) . ?
C16 C17 1.389(4) . ?
C16 H16 0.9500 . ?
C17 C18 1.386(4) . ?
C17 C21 1.510(3) . ?
C18 C19 1.398(3) . ?
C18 H18 0.9500 . ?
C19 C22 1.502(3) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
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
_geom_hbond_publ_flag
C12 H12C O3 0.98 2.60 3.190(3) 118.5 4_575 yes
C13 H13B O3 0.98 2.64 3.272(3) 122.6 4_575 yes
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 O2 N4 O3 3.0(3) . . . . ?
C10 N1 C1 C2 86.7(3) . . . . ?
Ni1 N1 C1 C2 -101.0(2) . . . . ?
C10 N1 C1 C6 -92.7(3) . . . . ?
Ni1 N1 C1 C6 79.6(3) . . . . ?
C6 C1 C2 C3 2.7(3) . . . . ?
N1 C1 C2 C3 -176.7(2) . . . . ?
C6 C1 C2 C7 -178.4(2) . . . . ?
N1 C1 C2 C7 2.2(3) . . . . ?
C1 C2 C3 C4 -1.2(4) . . . . ?
C7 C2 C3 C4 179.9(2) . . . . ?
C2 C3 C4 C5 -1.3(4) . . . . ?
C2 C3 C4 C8 176.8(2) . . . . ?
C3 C4 C5 C6 2.5(4) . . . . ?
C8 C4 C5 C6 -175.6(2) . . . . ?
C4 C5 C6 C1 -1.1(3) . . . . ?
C4 C5 C6 C9 178.1(2) . . . . ?
C2 C1 C6 C5 -1.5(3) . . . . ?
N1 C1 C6 C5 177.8(2) . . . . ?
C2 C1 C6 C9 179.2(2) . . . . ?
N1 C1 C6 C9 -1.5(3) . . . . ?
C1 N1 C10 C12 3.3(3) . . . . ?
Ni1 N1 C10 C12 -169.85(18) . . . . ?
C1 N1 C10 C11 -177.83(19) . . . . ?
Ni1 N1 C10 C11 9.0(3) . . . . ?
C14 N2 C11 C13 -1.0(3) . . . . ?
Ni1 N2 C11 C13 -178.97(18) . . . . ?
C14 N2 C11 C10 178.91(19) . . . . ?
Ni1 N2 C11 C10 1.0(2) . . . . ?
N1 C10 C11 N2 -6.7(3) . . . . ?
C12 C10 C11 N2 172.1(2) . . . . ?
N1 C10 C11 C13 173.2(2) . . . . ?
C12 C10 C11 C13 -7.9(3) . . . . ?
C11 N2 C14 C19 -79.2(3) . . . . ?
Ni1 N2 C14 C19 98.5(2) . . . . ?
C11 N2 C14 C15 103.7(3) . . . . ?
Ni1 N2 C14 C15 -78.6(2) . . . . ?
C19 C14 C15 C16 1.6(4) . . . . ?
N2 C14 C15 C16 178.7(2) . . . . ?
C19 C14 C15 C20 -179.4(2) . . . . ?
N2 C14 C15 C20 -2.4(3) . . . . ?
C14 C15 C16 C17 -1.2(4) . . . . ?
C20 C15 C16 C17 179.8(2) . . . . ?
C15 C16 C17 C18 0.5(4) . . . . ?
C15 C16 C17 C21 -179.6(2) . . . . ?
C16 C17 C18 C19 -0.1(4) . . . . ?
C21 C17 C18 C19 179.9(2) . . . . ?
C15 C14 C19 C18 -1.3(4) . . . . ?
N2 C14 C19 C18 -178.3(2) . . . . ?
C15 C14 C19 C22 178.2(2) . . . . ?
N2 C14 C19 C22 1.2(3) . . . . ?
C17 C18 C19 C14 0.5(4) . . . . ?
C17 C18 C19 C22 -179.0(2) . . . . ?
