#------------------------------------------------------------------------------
#$Date: 2025-08-20 21:19:29 +0200 (Wed 20 de Aug de 2025) $
#$Revision: 301836 $
#$URL: svn://www.crystallography.net/cod/cif/4/30/30/4303097.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_4303097
loop_
_publ_author_name
'Voltaire G. Organo'
'Alexander S. Filatov'
'Justin S. Quartararo'
'Zachary M. Friedman'
'Elena V. Rybak-Akimova'
_publ_contact_author_address
;
Department of Chemistry
Tufts University
Medford MA 02155
USA
;
_publ_contact_author_email       erybakak@granite.tufts.edu
_publ_contact_author_fax         617-627-3443
_publ_contact_author_name
;
Rybak-Akimova, Elena V. 
;
_publ_contact_author_phone       617-627-3413
_publ_section_title
;
Nickel(II) Complexes of Monofunctionalized Pyridine-Azamacrocycles:
Synthesis, Structures, Pendant Arm "On-Off" Coordination Equilibria,
and Peroxidase-like Activity
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              8456
_journal_page_last               8468
_journal_paper_doi               10.1021/ic901083u
_journal_volume                  48
_journal_year                    2009
_chemical_formula_moiety         'C22 H42 N5 Ni, 3(Cl O4)'
_chemical_formula_sum            'C22 H42 Cl3 N5 Ni O12'
_chemical_formula_weight         733.67
_chemical_name_systematic
; 
 (3-[(2R,12S)-2,12-dimethyl-3,7,11,17-tetrazabicyclo[11.3.1]-
heptadeca-1(16),13(17),14-trien-7-yl]-N,N-diethyl-propan-1-amine)
-nickel(II) triperchlorate
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.524(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.6725(13)
_cell_length_b                   9.3257(14)
_cell_length_c                   37.872(6)
_cell_measurement_reflns_used    5868
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.66
_cell_measurement_theta_min      2.41
_cell_volume                     3062.9(8)
_computing_cell_refinement       'SAINT Ver. 6.22  (Bruker-AXS, 2003)'
_computing_data_collection       'SMART Ver. 5.622 (Bruker-AXS, 2003)'
_computing_data_reduction        'SAINT Ver. 6.22'
_computing_molecular_graphics    'SHELXTL Ver. 6.14'
_computing_publication_material  'SHELXTL Ver. 6.14'
_computing_structure_refinement  'SHELXTL Ver. 6.14'
_computing_structure_solution    'SHELXTL Ver. 6.14 (Bruker-AXS, 2003)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area-detector'
_diffrn_measurement_method       '0.30° ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           Mo-K\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0579
_diffrn_reflns_av_sigmaI/netI    0.0504
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       45
_diffrn_reflns_limit_l_min       -46
_diffrn_reflns_number            22063
_diffrn_reflns_theta_full        26.02
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         2.15
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.963
_exptl_absorpt_correction_T_max  0.9625
_exptl_absorpt_correction_T_min  0.7811
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS  (Bruker-AXS, 2003)
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.591
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1536
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.872
_refine_diff_density_min         -0.399
_refine_diff_density_rms         0.075
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     484
_refine_ls_number_reflns         6017
_refine_ls_number_restraints     178
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0795
_refine_ls_R_factor_gt           0.0633
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0872P)²+5.4950P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1664
_refine_ls_wR_factor_ref         0.1759
_reflns_number_gt                4839
_reflns_number_total             6017
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ic901083u_si_001_4.cif
_cod_data_source_block           '[Ni(HLNEt2)](ClO4)3'
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_cell_volume        3062.8(8)
_cod_original_sg_symbol_Hall     '-P 2ybc     '
_cod_original_sg_symbol_H-M      'P 1 21/c 1 '
_cod_database_code               4303097
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Ni1 Ni 0.82613(6) 0.26896(6) 0.085093(13) 0.03320(18) Uani 1 1 d . . .
N1 N 0.8561(4) 0.4212(4) 0.05496(9) 0.0343(8) Uani 1 1 d . . .
N2 N 0.9246(4) 0.3952(4) 0.11949(10) 0.0422(9) Uani 1 1 d . . .
H23 H 0.8421 0.4389 0.1307 0.051 Uiso 1 1 calc R . .
N3 N 0.7016(4) 0.1924(4) 0.04621(9) 0.0358(8) Uani 1 1 d . . .
H24 H 0.6001 0.2096 0.0527 0.043 Uiso 1 1 calc R . .
N4 N 0.7813(4) 0.1102(4) 0.11779(9) 0.0369(8) Uani 1 1 d . . .
N5 N 0.4010(6) -0.0061(5) 0.21071(13) 0.0680(13) Uani 1 1 d DU . .
H5 H 0.4923 0.0063 0.2234 0.082 Uiso 1 1 calc R A 1
C1 C 0.7900(5) 0.4202(5) 0.02265(11) 0.0388(10) Uani 1 1 d . . .
C2 C 0.7955(6) 0.5410(5) 0.00116(13) 0.0481(12) Uani 1 1 d . . .
H2 H 0.7480 0.5409 -0.0215 0.058 Uiso 1 1 calc R . .
C3 C 0.8715(6) 0.6609(5) 0.01362(14) 0.0536(13) Uani 1 1 d . . .
H3 H 0.8752 0.7450 -0.0005 0.064 Uiso 1 1 calc R . .
C4 C 0.9420(6) 0.6602(5) 0.04618(14) 0.0496(12) Uani 1 1 d . . .
H4 H 0.9965 0.7422 0.0544 0.060 Uiso 1 1 calc R . .
C5 C 0.9323(5) 0.5382(5) 0.06687(13) 0.0423(10) Uani 1 1 d . . .
C6 C 1.0046(6) 0.5153(5) 0.10235(14) 0.0487(11) Uani 1 1 d . . .
H6 H 1.1126 0.4825 0.0981 0.058 Uiso 1 1 calc R . .
C7 C 1.0162(9) 0.6489(6) 0.12485(19) 0.079(2) Uani 1 1 d . . .
H7A H 0.9124 0.6831 0.1304 0.119 Uiso 1 1 calc R . .
H7B H 1.0717 0.7235 0.1119 0.119 Uiso 1 1 calc R . .
H7C H 1.0720 0.6267 0.1468 0.119 Uiso 1 1 calc R . .
C8 C 1.0197(7) 0.3381(6) 0.14905(13) 0.0579(13) Uani 1 1 d . . .
H8A H 1.0466 0.4170 0.1655 0.069 Uiso 1 1 calc R . .
H8B H 1.1168 0.2980 0.1397 0.069 Uiso 1 1 calc R . .
C9 C 0.9335(7) 0.2230(7) 0.16865(13) 0.0611(14) Uani 1 1 d . . .
H9A H 0.9945 0.1943 0.1897 0.073 Uiso 1 1 calc R . .
H9B H 0.8344 0.2628 0.1769 0.073 Uiso 1 1 calc R . .
C10 C 0.9019(6) 0.0926(5) 0.14644(12) 0.0470(11) Uani 1 1 d . . .
H10A H 0.8691 0.0138 0.1622 0.056 Uiso 1 1 calc R . .
H10B H 0.9995 0.0626 0.1353 0.056 Uiso 1 1 calc R . .
C11 C 0.7785(5) -0.0335(5) 0.09987(12) 0.0421(10) Uani 1 1 d . . .
H11A H 0.8828 -0.0531 0.0907 0.050 Uiso 1 1 calc R . .
H11B H 0.7563 -0.1075 0.1179 0.050 Uiso 1 1 calc R . .
C12 C 0.6651(5) -0.0506(5) 0.07023(12) 0.0441(10) Uani 1 1 d . . .
H12A H 0.5618 -0.0207 0.0784 0.053 Uiso 1 1 calc R . .
H12B H 0.6592 -0.1531 0.0635 0.053 Uiso 1 1 calc R . .
C13 C 0.7079(5) 0.0366(5) 0.03829(12) 0.0418(10) Uani 1 1 d . . .
H13A H 0.8134 0.0106 0.0308 0.050 Uiso 1 1 calc R . .
H13B H 0.6360 0.0143 0.0186 0.050 Uiso 1 1 calc R . .
C14 C 0.7239(5) 0.2779(5) 0.01312(11) 0.0422(10) Uani 1 1 d . . .
H14 H 0.8045 0.2268 -0.0008 0.051 Uiso 1 1 calc R . .
C15 C 0.5809(7) 0.2827(7) -0.00997(15) 0.0644(15) Uani 1 1 d . . .
H15A H 0.5010 0.3391 0.0018 0.097 Uiso 1 1 calc R . .
H15B H 0.5432 0.1850 -0.0140 0.097 Uiso 1 1 calc R . .
H15C H 0.6059 0.3272 -0.0327 0.097 Uiso 1 1 calc R . .
C16 C 0.6256(5) 0.1441(5) 0.13328(12) 0.0416(10) Uani 1 1 d . B .
H16A H 0.5516 0.1611 0.1137 0.050 Uiso 1 1 calc R . .
H16B H 0.6342 0.2343 0.1470 0.050 Uiso 1 1 calc R . .
C17 C 0.5605(6) 0.0281(6) 0.15722(13) 0.0496(12) Uani 1 1 d . . .
H17A H 0.5229 -0.0531 0.1427 0.060 Uiso 1 1 calc R B .
H17B H 0.6429 -0.0080 0.1731 0.060 Uiso 1 1 calc R . .
C18 C 0.4296(6) 0.0864(6) 0.17894(13) 0.0525(12) Uani 1 1 d . B .
H18A H 0.4548 0.1850 0.1867 0.063 Uiso 1 1 calc R . .
H18B H 0.3348 0.0907 0.1642 0.063 Uiso 1 1 calc R . .
C19 C 0.3968(13) -0.1622(11) 0.2068(3) 0.071(2) Uani 0.70 1 d PDU B 1
H19A H 0.3881 -0.2090 0.2301 0.085 Uiso 0.70 1 calc PR B 1
H19B H 0.4918 -0.1968 0.1952 0.085 Uiso 0.70 1 calc PR B 1
C20 C 0.2588(15) -0.1950(15) 0.1844(3) 0.098(4) Uani 0.70 1 d PDU B 1
H20A H 0.1671 -0.1520 0.1950 0.147 Uiso 0.70 1 calc PR B 1
H20B H 0.2453 -0.2991 0.1828 0.147 Uiso 0.70 1 calc PR B 1
H20C H 0.2734 -0.1553 0.1607 0.147 Uiso 0.70 1 calc PR B 1
C19X C 0.318(3) -0.131(2) 0.1949(9) 0.102(8) Uani 0.30 1 d PDU B 2
H19C H 0.2733 -0.0993 0.1721 0.122 Uiso 0.30 1 calc PR B 2
H19D H 0.2306 -0.1542 0.2106 0.122 Uiso 0.30 1 calc PR B 2
C20X C 0.404(4) -0.270(2) 0.1881(7) 0.106(9) Uani 0.30 1 d PDU B 2
H20D H 0.4534 -0.2659 0.1649 0.159 Uiso 0.30 1 calc PR B 2
H20E H 0.3316 -0.3509 0.1885 0.159 Uiso 0.30 1 calc PR B 2
H20F H 0.4833 -0.2843 0.2064 0.159 Uiso 0.30 1 calc PR B 2
C21 C 0.2887(9) 0.0568(8) 0.23469(17) 0.086(2) Uani 1 1 d . B .
H21A H 0.1845 0.0468 0.2241 0.104 Uiso 1 1 calc R . .
H21B H 0.3106 0.1605 0.2371 0.104 Uiso 1 1 calc R . .
C22 C 0.2889(12) -0.0111(11) 0.2713(2) 0.118(3) Uani 1 1 d . . .
H22A H 0.2481 -0.1089 0.2697 0.177 Uiso 1 1 calc R B .
H22B H 0.2242 0.0459 0.2870 0.177 Uiso 1 1 calc R . .
H22C H 0.3946 -0.0139 0.2806 0.177 Uiso 1 1 calc R . .
Cl1 Cl 0.8007(2) 0.97612(19) 0.25001(4) 0.0752(5) Uani 1 1 d U . .
O1 O 0.9326(15) 1.0519(19) 0.2644(6) 0.146(6) Uani 0.50 1 d PU C 1
O2 O 0.7389(19) 0.9053(13) 0.2795(3) 0.090(3) Uani 0.50 1 d PU C 1
O3 O 0.825(3) 0.877(2) 0.2224(4) 0.115(7) Uani 0.50 1 d PU C 1
O4 O 0.7044(18) 1.089(2) 0.2378(5) 0.077(4) Uani 0.50 1 d PU C 1
O1X O 0.863(3) 0.980(4) 0.2798(4) 0.223(10) Uani 0.50 1 d PU C 2
O2X O 0.659(2) 0.900(2) 0.2555(7) 0.195(8) Uani 0.50 1 d PU C 2
O3X O 0.893(3) 0.909(3) 0.2270(6) 0.147(10) Uani 0.50 1 d PU C 2
O4X O 0.745(4) 1.101(2) 0.2345(7) 0.156(9) Uani 0.50 1 d PU C 2
Cl2 Cl 0.48996(17) 0.52999(16) 0.10961(4) 0.0676(4) Uani 1 1 d . . .
O5 O 0.496(4) 0.433(3) 0.0775(8) 0.091(7) Uani 0.50 1 d PU D 1
O6 O 0.629(3) 0.582(4) 0.1174(12) 0.181(16) Uani 0.50 1 d PU D 1
O7 O 0.393(2) 0.451(2) 0.1331(6) 0.103(7) Uani 0.50 1 d PU D 1
O8 O 0.394(3) 0.642(3) 0.1069(8) 0.189(13) Uani 0.50 1 d PU D 1
O5X O 0.519(3) 0.451(3) 0.0800(7) 0.095(9) Uani 0.50 1 d PU D 2
O6X O 0.622(3) 0.533(3) 0.1300(9) 0.152(12) Uani 0.50 1 d PU D 2
O7X O 0.419(3) 0.451(2) 0.1350(7) 0.150(12) Uani 0.50 1 d PU D 2
O8X O 0.410(3) 0.6582(16) 0.1006(5) 0.105(7) Uani 0.50 1 d PU D 2
Cl3 Cl 0.21369(12) 0.07607(12) 0.06541(3) 0.0397(3) Uani 1 1 d . . .
O9 O 0.1105(5) 0.1942(5) 0.06820(12) 0.0775(13) Uani 1 1 d . . .
O10 O 0.3454(4) 0.1170(4) 0.04527(9) 0.0541(9) Uani 1 1 d . . .
O11 O 0.2599(5) 0.0332(6) 0.09992(11) 0.0906(16) Uani 1 1 d . . .
O12 O 0.1347(6) -0.0359(6) 0.04787(15) 0.107(2) Uani 1 1 d . . .
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'
Cl Cl 0.1484 0.1585 '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
N1 Ni1 N2 83.39(16) . . yes
N1 Ni1 N3 83.95(15) . . yes
N2 Ni1 N3 164.01(15) . . yes
N1 Ni1 N4 176.55(14) . . yes
N2 Ni1 N4 97.00(16) . . yes
N3 Ni1 N4 95.06(15) . . yes
C1 N1 C5 120.8(4) . . yes
C1 N1 Ni1 119.8(3) . . yes
C5 N1 Ni1 119.1(3) . . yes
C6 N2 C8 110.2(4) . . yes
C6 N2 Ni1 111.8(3) . . yes
C8 N2 Ni1 121.7(3) . . yes
C6 N2 H23 103.7 . . ?
C8 N2 H23 103.7 . . ?
Ni1 N2 H23 103.7 . . ?
C13 N3 C14 110.3(3) . . yes
C13 N3 Ni1 119.3(3) . . yes
C14 N3 Ni1 111.2(3) . . yes
C13 N3 H24 104.9 . . ?
C14 N3 H24 104.9 . . ?
Ni1 N3 H24 104.9 . . ?
C11 N4 C10 103.6(3) . . yes
C11 N4 C16 110.6(3) . . yes
C10 N4 C16 111.1(3) . . yes
C11 N4 Ni1 112.9(3) . . yes
C10 N4 Ni1 113.2(3) . . yes
C16 N4 Ni1 105.6(3) . . yes
C21 N5 C19 116.5(6) . . yes
C21 N5 C19X 104.0(13) . . yes
C21 N5 C18 112.5(5) . . yes
C19 N5 C18 119.5(6) . . yes
C19X N5 C18 102.1(15) . . yes
C21 N5 H5 101.4 . . ?
C19 N5 H5 101.4 . . ?
C19X N5 H5 135.2 . . ?
C18 N5 H5 101.4 . . ?
N1 C1 C2 120.6(4) . . yes
N1 C1 C14 112.7(4) . . yes
C2 C1 C14 126.5(4) . . yes
C3 C2 C1 118.4(5) . . yes
C3 C2 H2 120.8 . . ?
C1 C2 H2 120.8 . . ?
C4 C3 C2 120.8(5) . . yes
C4 C3 H3 119.6 . . ?
C2 C3 H3 119.6 . . ?
C3 C4 C5 119.0(5) . . yes
C3 C4 H4 120.5 . . ?
C5 C4 H4 120.5 . . ?
N1 C5 C4 120.4(5) . . yes
N1 C5 C6 112.6(4) . . yes
C4 C5 C6 126.9(5) . . yes
N2 C6 C5 108.1(4) . . yes
N2 C6 C7 114.1(5) . . yes
C5 C6 C7 114.5(4) . . yes
N2 C6 H6 106.6 . . ?
C5 C6 H6 106.6 . . ?
C7 C6 H6 106.6 . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N2 C8 C9 110.6(4) . . yes
N2 C8 H8A 109.5 . . ?
C9 C8 H8A 109.5 . . ?
N2 C8 H8B 109.5 . . ?
C9 C8 H8B 109.5 . . ?
H8A C8 H8B 108.1 . . ?
C10 C9 C8 112.9(4) . . yes
C10 C9 H9A 109.0 . . ?
C8 C9 H9A 109.0 . . ?
C10 C9 H9B 109.0 . . ?
C8 C9 H9B 109.0 . . ?
H9A C9 H9B 107.8 . . ?
C9 C10 N4 115.9(4) . . yes
C9 C10 H10A 108.3 . . ?
N4 C10 H10A 108.3 . . ?
C9 C10 H10B 108.3 . . ?
N4 C10 H10B 108.3 . . ?
H10A C10 H10B 107.4 . . ?
C12 C11 N4 116.3(4) . . yes
C12 C11 H11A 108.2 . . ?
N4 C11 H11A 108.2 . . ?
C12 C11 H11B 108.2 . . ?
N4 C11 H11B 108.2 . . ?
H11A C11 H11B 107.4 . . ?
C11 C12 C13 112.4(4) . . yes
C11 C12 H12A 109.1 . . ?
C13 C12 H12A 109.1 . . ?
C11 C12 H12B 109.1 . . ?
C13 C12 H12B 109.1 . . ?
H12A C12 H12B 107.9 . . ?
N3 C13 C12 110.9(4) . . yes
N3 C13 H13A 109.5 . . ?
C12 C13 H13A 109.5 . . ?
N3 C13 H13B 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 108.1 . . ?
C1 C14 N3 108.9(4) . . yes
C1 C14 C15 115.2(4) . . yes
N3 C14 C15 112.9(4) . . yes
C1 C14 H14 106.4 . . ?
N3 C14 H14 106.4 . . ?
C15 C14 H14 106.4 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N4 C16 C17 114.9(4) . . yes
N4 C16 H16A 108.6 . . ?
C17 C16 H16A 108.6 . . ?
N4 C16 H16B 108.6 . . ?
C17 C16 H16B 108.6 . . ?
H16A C16 H16B 107.5 . . ?
C18 C17 C16 110.7(4) . . yes
C18 C17 H17A 109.5 . . ?
C16 C17 H17A 109.5 . . ?
C18 C17 H17B 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 108.1 . . ?
N5 C18 C17 111.1(4) . . yes
N5 C18 H18A 109.4 . . ?
C17 C18 H18A 109.4 . . ?
N5 C18 H18B 109.4 . . ?
C17 C18 H18B 109.4 . . ?
H18A C18 H18B 108.0 . . ?
N5 C19 C20 106.3(9) . . yes
N5 C19 H19A 110.5 . . ?
C20 C19 H19A 110.5 . . ?
N5 C19 H19B 110.5 . . ?
C20 C19 H19B 110.5 . . ?
H19A C19 H19B 108.7 . . ?
N5 C19X C20X 120(2) . . yes
N5 C19X H19C 107.3 . . ?
C20X C19X H19C 107.3 . . ?
N5 C19X H19D 107.3 . . ?
C20X C19X H19D 107.3 . . ?
H19C C19X H19D 106.9 . . ?
C19X C20X H20D 109.5 . . ?
C19X C20X H20E 109.5 . . ?
H20D C20X H20E 109.5 . . ?
C19X C20X H20F 109.5 . . ?
H20D C20X H20F 109.5 . . ?
H20E C20X H20F 109.5 . . ?
N5 C21 C22 113.8(6) . . yes
N5 C21 H21A 108.8 . . ?
C22 C21 H21A 108.8 . . ?
N5 C21 H21B 108.8 . . ?
C22 C21 H21B 108.8 . . ?
H21A C21 H21B 107.7 . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
O1X Cl1 O3X 110.3(16) . . ?
O1X Cl1 O4X 120(2) . . ?
O3X Cl1 O4X 108.7(17) . . ?
O2 Cl1 O3 110.0(10) . . ?
O2 Cl1 O4 112.2(10) . . ?
O3 Cl1 O4 109.6(10) . . ?
O1X Cl1 O2X 104.3(17) . . ?
O3X Cl1 O2X 112.3(16) . . ?
O4X Cl1 O2X 100.3(16) . . ?
O2 Cl1 O1 103.6(10) . . ?
O3 Cl1 O1 118.4(13) . . ?
O4 Cl1 O1 102.8(10) . . ?
O6 Cl2 O8 107(2) . . ?
O7X Cl2 O5X 112.2(18) . . ?
O8 Cl2 O6X 123(2) . . ?
O7X Cl2 O6X 89.7(19) . . ?
O5X Cl2 O6X 108.1(19) . . ?
O7X Cl2 O8X 113.5(12) . . ?
O5X Cl2 O8X 110.5(15) . . ?
O6X Cl2 O8X 121.2(17) . . ?
O6 Cl2 O7 126(2) . . ?
O8 Cl2 O7 94.7(15) . . ?
O6 Cl2 O5 111(2) . . ?
O8 Cl2 O5 115.4(19) . . ?
O7 Cl2 O5 102.5(15) . . ?
O12 Cl3 O11 110.9(4) . . ?
O12 Cl3 O9 107.7(3) . . ?
O11 Cl3 O9 108.8(3) . . ?
O12 Cl3 O10 109.4(2) . . ?
O11 Cl3 O10 110.2(2) . . ?
O9 Cl3 O10 109.8(2) . . ?
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 N1 1.842(3) . yes
Ni1 N2 1.947(4) . yes
Ni1 N3 1.953(4) . yes
Ni1 N4 1.971(4) . yes
N1 C1 1.346(6) . yes
N1 C5 1.351(6) . yes
N2 C6 1.471(6) . yes
N2 C8 1.483(6) . yes
N2 H23 0.9300 . ?
N3 C13 1.485(6) . yes
N3 C14 1.499(5) . yes
N3 H24 0.9300 . ?
N4 C11 1.502(6) . yes
N4 C10 1.509(6) . yes
N4 C16 1.510(5) . yes
N5 C21 1.461(7) . yes
N5 C19 1.464(11) . yes
N5 C19X 1.493(10) . yes
N5 C18 1.503(6) . yes
N5 H5 0.9300 . ?
C1 C2 1.391(6) . yes
C1 C14 1.489(7) . yes
C2 C3 1.380(8) . yes
C2 H2 0.9500 . ?
C3 C4 1.371(8) . yes
C3 H3 0.9500 . ?
C4 C5 1.385(6) . yes
C4 H4 0.9500 . ?
C5 C6 1.493(7) . yes
C6 C7 1.513(7) . yes
C6 H6 1.0000 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 C9 1.507(8) . yes
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.503(7) . yes
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.494(6) . yes
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.507(6) . yes
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.511(7) . yes
C14 H14 1.0000 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 C17 1.523(6) . yes
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C18 1.508(7) . yes
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 C20 1.492(13) . yes
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C19X C20X 1.52(2) . yes
C19X H19C 0.9900 . ?
C19X H19D 0.9900 . ?
C20X H20D 0.9800 . ?
C20X H20E 0.9800 . ?
C20X H20F 0.9800 . ?
C21 C22 1.522(9) . yes
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
Cl1 O1X 1.244(16) . ?
Cl1 O3X 1.34(2) . ?
Cl1 O4X 1.39(2) . ?
Cl1 O2 1.408(10) . ?
Cl1 O3 1.409(19) . ?
Cl1 O4 1.419(17) . ?
Cl1 O2X 1.436(17) . ?
Cl1 O1 1.447(13) . ?
Cl2 O6 1.33(2) . ?
Cl2 O8 1.34(2) . ?
Cl2 O7X 1.362(19) . ?
Cl2 O5X 1.37(2) . ?
Cl2 O6X 1.38(2) . ?
Cl2 O8X 1.423(14) . ?
Cl2 O7 1.434(17) . ?
Cl2 O5 1.51(3) . ?
Cl3 O12 1.412(5) . ?
Cl3 O11 1.421(4) . ?
Cl3 O9 1.424(4) . ?
Cl3 O10 1.431(3) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139127039
