#------------------------------------------------------------------------------
#$Date: 2019-11-17 09:38:59 +0200 (Sun, 17 Nov 2019) $
#$Revision: 229153 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/15/7231501.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_7231501
loop_
_publ_author_name
'Lian, Zhaoxun'
'Zhao, Ning'
'Liu, Ping'
'An, Caixia'
'Wang, Airong'
'Yang, Fengxia'
_publ_section_title
;
 Crystal structures and investigation of the third-order nonlinear optical
 properties of four coordination polymers by using the Z-scan technique
;
_journal_issue                   38
_journal_name_full               CrystEngComm
_journal_page_first              5833
_journal_paper_doi               10.1039/C8CE01283K
_journal_volume                  20
_journal_year                    2018
_chemical_formula_moiety         'C23 H24 N4 Ni O6, H2 O'
_chemical_formula_sum            'C23 H26 N4 Ni O7'
_chemical_formula_weight         529.19
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2016-12-09
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_audit_update_record
;
2018-02-11 deposited with the CCDC.
2018-09-10 downloaded from the CCDC.
;
_cell_angle_alpha                103.5140(10)
_cell_angle_beta                 107.5220(10)
_cell_angle_gamma                95.5320(10)
_cell_formula_units_Z            2
_cell_length_a                   10.0679(6)
_cell_length_b                   11.2018(7)
_cell_length_c                   11.3853(7)
_cell_measurement_reflns_used    7977
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.47
_cell_measurement_theta_min      2.95
_cell_volume                     1171.13(12)
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_collection       'Nonius CAD4 software'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 5.6
_diffrn_detector_type            'Bruker SMART CCD 6000 area detector'
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART CCD 6000 area detector'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0243
_diffrn_reflns_av_unetI/netI     0.0277
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            14253
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.518
_diffrn_reflns_theta_min         1.952
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_target            Mo
_exptl_absorpt_coefficient_mu    0.881
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6781
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0492 before and 0.0378 after correction.
The Ratio of minimum to maximum transmission is 0.9095.
The λ/2 correction factor is 0.0015.
;
_exptl_crystal_colour            green
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.501
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.546
_refine_diff_density_min         -0.618
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     321
_refine_ls_number_reflns         5309
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0357
_refine_ls_R_factor_gt           0.0312
_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)+(0.0420P)²+0.5250P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0825
_refine_ls_wR_factor_ref         0.0856
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4749
_reflns_number_total             5309
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c8ce01283k2.cif
_cod_data_source_block           r12
_cod_depositor_comments
'Adding full bibliography for 7231500--7231503.cif.'
_cod_database_code               7231501
_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.
;
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All O(H,H) groups
2.a Free rotating group:
 O7(H,HA)
2.b Rotating group:
 O6(H6A,H6B), O5(H5A,H5B)
2.c Secondary CH2 refined with riding coordinates:
 C19(H19A,H19B), C7(H7A,H7B), C15(H15A,H15B)
2.d Aromatic/amide H refined with riding coordinates:
 C20(H20), C18(H18), C10(H10), C4(H4), C2(H2), C13(H13), C22(H22), C16(H16),
 C17(H17), C21(H21), C5(H5), C3(H3), C12(H12), C11(H11)
;
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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
Ni1 Ni 0.96244(2) 0.43085(2) 0.74108(2) 0.02446(8) Uani 1 1 d .
O6 O 1.12117(12) 0.56567(11) 0.89641(11) 0.0306(3) Uani 1 1 d .
H6A H 1.1121 0.5607 0.9676 0.046 Uiso 1 1 d GR
H6B H 1.1128 0.6391 0.8888 0.046 Uiso 1 1 d GR
O3 O 0.90273(13) 0.57427(12) 0.36565(12) 0.0330(3) Uani 1 1 d .
O2 O 1.02677(15) 0.74588(13) 0.80051(14) 0.0448(3) Uani 1 1 d .
O1 O 0.87076(14) 0.57308(12) 0.68332(14) 0.0408(3) Uani 1 1 d .
O4 O 0.69246(14) 0.49790(16) 0.21386(13) 0.0496(4) Uani 1 1 d .
O5 O 0.82406(14) 0.43324(13) 0.84910(12) 0.0380(3) Uani 1 1 d .
H5A H 0.7721 0.4915 0.8403 0.057 Uiso 1 1 d GR
H5B H 0.8720 0.4481 0.9311 0.057 Uiso 1 1 d GR
N1 N 0.80799(15) 0.31476(13) 0.57930(13) 0.0275(3) Uani 1 1 d .
N2 N 0.68039(14) 0.23411(13) 0.37560(13) 0.0269(3) Uani 1 1 d .
N3 N 0.86531(16) -0.11701(13) 0.19064(15) 0.0327(3) Uani 1 1 d .
N4 N 0.95729(15) -0.28731(13) 0.19185(14) 0.0293(3) Uani 1 1 d .
C14 C 0.64020(17) -0.03913(15) 0.17792(15) 0.0272(3) Uani 1 1 d .
C9 C 0.56425(17) 0.05929(15) 0.18189(15) 0.0269(3) Uani 1 1 d .
C8 C 0.77031(18) 0.54801(15) 0.32831(16) 0.0289(3) Uani 1 1 d .
C00F C 0.91575(18) 0.68819(15) 0.71103(16) 0.0280(3) Uani 1 1 d .
C19 C 0.63769(18) 0.19431(15) 0.23493(15) 0.0284(3) Uani 1 1 d .
H19A H 0.7207 0.2047 0.2094 0.034 Uiso 1 1 calc R
H19B H 0.5743 0.2466 0.1994 0.034 Uiso 1 1 calc R
C20 C 0.80933(17) 0.28971(15) 0.46076(16) 0.0282(3) Uani 1 1 d .
H20 H 0.8891 0.3080 0.4386 0.034 Uiso 1 1 calc R
C7 C 0.69988(19) 0.57773(18) 0.43017(17) 0.0343(4) Uani 1 1 d .
H7A H 0.5980 0.5552 0.3893 0.041 Uiso 1 1 calc R
H7B H 0.7284 0.5275 0.4891 0.041 Uiso 1 1 calc R
C15 C 0.80044(19) -0.01051(16) 0.2302(2) 0.0365(4) Uani 1 1 d .
H15A H 0.8336 0.0579 0.2013 0.044 Uiso 1 1 calc R
H15B H 0.8311 0.0165 0.3231 0.044 Uiso 1 1 calc R
C18 C 0.91036(18) -0.19768(16) 0.25797(17) 0.0306(3) Uani 1 1 d .
H18 H 0.9088 -0.1914 0.3404 0.037 Uiso 1 1 calc R
C10 C 0.41710(19) 0.03189(19) 0.13835(18) 0.0382(4) Uani 1 1 d .
H10 H 0.3661 0.0969 0.1401 0.046 Uiso 1 1 calc R
C1 C 0.82989(18) 0.76337(16) 0.63135(17) 0.0288(3) Uani 1 1 d .
C4 C 0.6949(2) 0.9239(2) 0.5001(2) 0.0479(5) Uani 1 1 d .
H4 H 0.6512 0.9767 0.4548 0.058 Uiso 1 1 calc R
C2 C 0.8482(2) 0.89165(17) 0.6908(2) 0.0372(4) Uani 1 1 d .
H2 H 0.9072 0.9239 0.7756 0.045 Uiso 1 1 calc R
C13 C 0.5661(2) -0.16134(17) 0.12988(18) 0.0366(4) Uani 1 1 d .
H13 H 0.6159 -0.2271 0.1260 0.044 Uiso 1 1 calc R
C6 C 0.73779(18) 0.71444(17) 0.50498(17) 0.0301(3) Uani 1 1 d .
C22 C 0.5919(2) 0.22378(19) 0.44481(18) 0.0398(4) Uani 1 1 d .
H22 H 0.4959 0.1896 0.4124 0.048 Uiso 1 1 calc R
C16 C 0.8854(2) -0.15687(19) 0.07480(19) 0.0398(4) Uani 1 1 d .
H16 H 0.8647 -0.1192 0.0083 0.048 Uiso 1 1 calc R
C17 C 0.9412(2) -0.26169(18) 0.07649(18) 0.0376(4) Uani 1 1 d .
H17 H 0.9651 -0.3093 0.0098 0.045 Uiso 1 1 calc R
C21 C 0.6714(2) 0.27297(18) 0.56931(18) 0.0378(4) Uani 1 1 d .
H21 H 0.6386 0.2778 0.6381 0.045 Uiso 1 1 calc R
C5 C 0.6741(2) 0.7975(2) 0.4407(2) 0.0410(4) Uani 1 1 d .
H5 H 0.6161 0.7667 0.3555 0.049 Uiso 1 1 calc R
C3 C 0.7804(2) 0.97128(19) 0.6260(2) 0.0462(5) Uani 1 1 d .
H3 H 0.7925 1.0557 0.6673 0.055 Uiso 1 1 calc R
C12 C 0.4194(2) -0.18679(19) 0.0877(2) 0.0443(5) Uani 1 1 d .
H12 H 0.3716 -0.2690 0.0564 0.053 Uiso 1 1 calc R
C11 C 0.3449(2) -0.0902(2) 0.0924(2) 0.0469(5) Uani 1 1 d .
H11 H 0.2465 -0.1068 0.0648 0.056 Uiso 1 1 calc R
O7 O 0.5982(3) 0.5513(5) 0.8769(5) 0.214(3) Uani 1 1 d .
H H 0.5231 0.5114 0.8791 0.321 Uiso 1 1 d G
HA H 0.5812 0.5690 0.8058 0.321 Uiso 1 1 d G
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
O3 Ni1 O6 89.23(5) 2_766 .
O3 Ni1 O5 179.17(5) 2_766 .
O1 Ni1 O6 89.50(5) . .
O1 Ni1 O3 95.17(6) . 2_766
O1 Ni1 O5 85.41(6) . .
O1 Ni1 N1 85.09(5) . .
O1 Ni1 N4 175.00(6) . 2_756
O5 Ni1 O6 91.37(5) . .
N1 Ni1 O6 173.64(5) . .
N1 Ni1 O3 87.95(5) . 2_766
N1 Ni1 O5 91.52(6) . .
N1 Ni1 N4 94.92(6) . 2_756
N4 Ni1 O6 90.77(5) 2_756 .
N4 Ni1 O3 89.82(5) 2_756 2_766
N4 Ni1 O5 89.60(5) 2_756 .
Ni1 O6 H6A 109.9 . .
Ni1 O6 H6B 109.8 . .
H6A O6 H6B 109.1 . .
C8 O3 Ni1 129.39(11) . 2_766
C00F O1 Ni1 132.08(12) . .
Ni1 O5 H5A 111.4 . .
Ni1 O5 H5B 110.8 . .
H5A O5 H5B 107.7 . .
C20 N1 Ni1 126.91(12) . .
C20 N1 C21 105.53(14) . .
C21 N1 Ni1 125.93(12) . .
C20 N2 C19 128.03(14) . .
C20 N2 C22 106.80(14) . .
C22 N2 C19 125.15(14) . .
C18 N3 C15 126.58(16) . .
C18 N3 C16 107.17(15) . .
C16 N3 C15 126.18(16) . .
C18 N4 Ni1 124.36(12) . 2_756
C18 N4 C17 105.55(14) . .
C17 N4 Ni1 130.09(12) . 2_756
C9 C14 C15 119.45(15) . .
C13 C14 C9 119.03(16) . .
C13 C14 C15 121.49(16) . .
C14 C9 C19 121.90(15) . .
C10 C9 C14 118.98(16) . .
C10 C9 C19 119.10(15) . .
O3 C8 O4 124.83(17) . .
O3 C8 C7 116.95(15) . .
O4 C8 C7 118.21(15) . .
O2 C00F O1 124.58(15) . .
O2 C00F C1 117.40(15) . .
O1 C00F C1 118.02(15) . .
N2 C19 C9 111.11(13) . .
N2 C19 H19A 109.4 . .
N2 C19 H19B 109.4 . .
C9 C19 H19A 109.4 . .
C9 C19 H19B 109.4 . .
H19A C19 H19B 108.0 . .
N1 C20 N2 111.40(15) . .
N1 C20 H20 124.3 . .
N2 C20 H20 124.3 . .
C8 C7 H7A 109.1 . .
C8 C7 H7B 109.1 . .
H7A C7 H7B 107.8 . .
C6 C7 C8 112.59(14) . .
C6 C7 H7A 109.1 . .
C6 C7 H7B 109.1 . .
N3 C15 C14 113.19(14) . .
N3 C15 H15A 108.9 . .
N3 C15 H15B 108.9 . .
C14 C15 H15A 108.9 . .
C14 C15 H15B 108.9 . .
H15A C15 H15B 107.8 . .
N3 C18 H18 124.4 . .
N4 C18 N3 111.25(16) . .
N4 C18 H18 124.4 . .
C9 C10 H10 119.3 . .
C11 C10 C9 121.33(18) . .
C11 C10 H10 119.3 . .
C2 C1 C00F 116.11(16) . .
C6 C1 C00F 124.83(15) . .
C6 C1 C2 119.05(16) . .
C5 C4 H4 120.0 . .
C3 C4 H4 120.0 . .
C3 C4 C5 119.90(18) . .
C1 C2 H2 119.2 . .
C3 C2 C1 121.57(19) . .
C3 C2 H2 119.2 . .
C14 C13 H13 119.4 . .
C12 C13 C14 121.15(18) . .
C12 C13 H13 119.4 . .
C1 C6 C7 125.57(15) . .
C1 C6 C5 118.09(17) . .
C5 C6 C7 116.34(17) . .
N2 C22 H22 126.8 . .
C21 C22 N2 106.43(16) . .
C21 C22 H22 126.8 . .
N3 C16 H16 126.8 . .
C17 C16 N3 106.34(16) . .
C17 C16 H16 126.8 . .
N4 C17 H17 125.2 . .
C16 C17 N4 109.67(16) . .
C16 C17 H17 125.2 . .
N1 C21 H21 125.1 . .
C22 C21 N1 109.83(16) . .
C22 C21 H21 125.1 . .
C4 C5 C6 122.1(2) . .
C4 C5 H5 119.0 . .
C6 C5 H5 119.0 . .
C4 C3 C2 119.21(19) . .
C4 C3 H3 120.4 . .
C2 C3 H3 120.4 . .
C13 C12 H12 120.1 . .
C11 C12 C13 119.83(18) . .
C11 C12 H12 120.1 . .
C10 C11 H11 120.2 . .
C12 C11 C10 119.67(18) . .
C12 C11 H11 120.2 . .
H O7 HA 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Ni1 O6 2.1323(12) .
Ni1 O3 2.0732(12) 2_766
Ni1 O1 2.0568(12) .
Ni1 O5 2.1161(13) .
Ni1 N1 2.0659(14) .
Ni1 N4 2.0675(14) 2_756
O6 H6A 0.8566 .
O6 H6B 0.8564 .
O3 Ni1 2.0732(12) 2_766
O3 C8 1.253(2) .
O2 C00F 1.254(2) .
O1 C00F 1.256(2) .
O4 C8 1.259(2) .
O5 H5A 0.8800 .
O5 H5B 0.8794 .
N1 C20 1.317(2) .
N1 C21 1.371(2) .
N2 C19 1.471(2) .
N2 C20 1.348(2) .
N2 C22 1.369(2) .
N3 C15 1.459(2) .
N3 C18 1.343(2) .
N3 C16 1.372(3) .
N4 Ni1 2.0674(14) 2_756
N4 C18 1.323(2) .
N4 C17 1.375(2) .
C14 C9 1.401(2) .
C14 C15 1.514(2) .
C14 C13 1.392(2) .
C9 C19 1.512(2) .
C9 C10 1.391(2) .
C8 C7 1.523(2) .
C00F C1 1.518(2) .
C19 H19A 0.9700 .
C19 H19B 0.9700 .
C20 H20 0.9300 .
C7 H7A 0.9700 .
C7 H7B 0.9700 .
C7 C6 1.516(3) .
C15 H15A 0.9700 .
C15 H15B 0.9700 .
C18 H18 0.9300 .
C10 H10 0.9300 .
C10 C11 1.385(3) .
C1 C2 1.406(2) .
C1 C6 1.400(3) .
C4 H4 0.9300 .
C4 C5 1.384(3) .
C4 C3 1.376(3) .
C2 H2 0.9300 .
C2 C3 1.389(3) .
C13 H13 0.9300 .
C13 C12 1.386(3) .
C6 C5 1.401(2) .
C22 H22 0.9300 .
C22 C21 1.349(3) .
C16 H16 0.9300 .
C16 C17 1.351(3) .
C17 H17 0.9300 .
C21 H21 0.9300 .
C5 H5 0.9300 .
C3 H3 0.9300 .
C12 H12 0.9300 .
C12 C11 1.375(3) .
C11 H11 0.9300 .
O7 H 0.8499 .
O7 HA 0.8498 .
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
Ni1 O3 C8 O4 8.9(3) 2_766
Ni1 O3 C8 C7 -171.99(11) 2_766
Ni1 O1 C00F O2 -11.8(3) .
Ni1 O1 C00F C1 168.51(12) .
Ni1 N1 C20 N2 -165.99(11) .
Ni1 N1 C21 C22 165.91(14) .
Ni1 N4 C18 N3 179.65(11) 2_756
Ni1 N4 C17 C16 -179.29(13) 2_756
O3 C8 C7 C6 57.4(2) .
O2 C00F C1 C2 -23.7(2) .
O2 C00F C1 C6 155.24(17) .
O1 C00F C1 C2 156.04(17) .
O1 C00F C1 C6 -25.0(2) .
O4 C8 C7 C6 -123.49(18) .
N2 C22 C21 N1 0.4(2) .
N3 C16 C17 N4 -0.5(2) .
C14 C9 C19 N2 -82.09(19) .
C14 C9 C10 C11 0.5(3) .
C14 C13 C12 C11 0.4(3) .
C9 C14 C15 N3 -165.05(16) .
C9 C14 C13 C12 -0.8(3) .
C9 C10 C11 C12 -0.9(3) .
C8 C7 C6 C1 -106.24(19) .
C8 C7 C6 C5 73.85(19) .
C00F C1 C2 C3 177.16(17) .
C00F C1 C6 C7 4.9(3) .
C00F C1 C6 C5 -175.22(16) .
C19 N2 C20 N1 178.52(14) .
C19 N2 C22 C21 -178.76(16) .
C19 C9 C10 C11 -178.11(17) .
C20 N1 C21 C22 -0.3(2) .
C20 N2 C19 C9 127.82(17) .
C20 N2 C22 C21 -0.4(2) .
C7 C6 C5 C4 177.08(17) .
C15 N3 C18 N4 176.76(16) .
C15 N3 C16 C17 -176.65(17) .
C15 C14 C9 C19 1.1(2) .
C15 C14 C9 C10 -177.46(16) .
C15 C14 C13 C12 176.96(18) .
C18 N3 C15 C14 -96.2(2) .
C18 N3 C16 C17 0.5(2) .
C18 N4 C17 C16 0.2(2) .
C10 C9 C19 N2 96.47(18) .
C1 C2 C3 C4 -1.0(3) .
C1 C6 C5 C4 -2.8(3) .
C2 C1 C6 C7 -176.22(16) .
C2 C1 C6 C5 3.7(2) .
C13 C14 C9 C19 178.93(15) .
C13 C14 C9 C10 0.4(2) .
C13 C14 C15 N3 17.2(3) .
C13 C12 C11 C10 0.5(3) .
C6 C1 C2 C3 -1.8(3) .
C22 N2 C19 C9 -54.2(2) .
C22 N2 C20 N1 0.2(2) .
C16 N3 C15 C14 80.4(2) .
C16 N3 C18 N4 -0.4(2) .
C17 N4 C18 N3 0.1(2) .
C21 N1 C20 N2 0.1(2) .
C5 C4 C3 C2 2.0(3) .
C3 C4 C5 C6 0.0(3) .
