# Supplementary Material (ESI) for Chemical Communications
# This journal is (c) The Royal Society of Chemistry 2009

data_global

_journal_coden_Cambridge         182

loop_
_publ_author_name
'Elena Rybak-Akimova'
'A.S Filatov'
'Jeffrey P Wikstrom'

_publ_contact_author_name        'Elena Rybak-Akimova'
_publ_contact_author_email       ELENA.RYBAK-AKIMOVA@TUFTS.EDU

_publ_section_title              
;
Condensation of nitriles with amides promoted by
coordinatively unsaturated bis-nickel(II)-hydroxy complex: a new
route to alkyl- and aryl-imidoylamidines
;

# Attachment 'nitrile_final.cif'

data_3
_database_code_depnum_ccdc_archive 'CCDC 748549'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
(2-pyridylmethyl)tert-butylamine nickel (II)
bis(imino(phenyl)methyl)amide perchlorate
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C30 H33 N6 Ni, Cl O4'
_chemical_formula_sum            'C30 H33 Cl N6 Ni O4'
_chemical_formula_weight         635.78

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P 1 21/n 1 '
_symmetry_space_group_name_Hall  '-P 2yn '
_symmetry_int_tables_number      14

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'

_cell_length_a                   12.3250(9)
_cell_length_b                   17.1390(12)
_cell_length_c                   14.1153(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 104.3250(10)
_cell_angle_gamma                90.00
_cell_volume                     2889.0(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    9501
_cell_measurement_theta_min      2.29
_cell_measurement_theta_max      26.97

_exptl_crystal_description       plate
_exptl_crystal_colour            brown
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.462
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1328
_exptl_absorpt_coefficient_mu    0.812
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS (Bruker-AXS, 2003)
;
_exptl_absorpt_correction_T_min  0.8677
_exptl_absorpt_correction_T_max  0.9683

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           Mo-K\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area-detector'
_diffrn_measurement_method       '0.30\% \w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            24185
_diffrn_reflns_av_R_equivalents  0.0408
_diffrn_reflns_av_sigmaI/netI    0.0384
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.91
_diffrn_reflns_theta_max         27.03
_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.999
_reflns_number_total             6292
_reflns_number_gt                4854
_reflns_threshold_expression     I>2\s(I)

_computing_data_collection       'SMART Ver. 5.622 (Bruker-AXS, 2003)'
_computing_cell_refinement       'SAINT Ver. 6.22 (Bruker-AXS, 2003)'
_computing_data_reduction        'SAINT Ver. 6.22'
_computing_structure_solution    'SHELXTL Ver. 6.14 (Bruker-AXS, 2003)'
_computing_structure_refinement  'SHELXTL Ver. 6.14'
_computing_molecular_graphics    'SHELXTL Ver. 6.14'
_computing_publication_material  'SHELXTL Ver. 6.14'

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0543P)^2^+1.4532P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         6292
_refine_ls_number_parameters     388
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0619
_refine_ls_R_factor_gt           0.0443
_refine_ls_wR_factor_ref         0.1128
_refine_ls_wR_factor_gt          0.1020
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_restrained_S_all      1.019
_refine_diff_density_max         0.615
_refine_diff_density_min         -0.356
_refine_diff_density_rms         0.068
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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 0.64412(2) 0.380865(18) 0.81195(2) 0.02495(10) Uani 1 1 d . . .
N1 N 0.49025(18) 0.38659(12) 0.78096(15) 0.0275(5) Uani 1 1 d . . .
H1N H 0.458(2) 0.3896(16) 0.824(2) 0.033 Uiso 1 1 d . . .
N2 N 0.44858(17) 0.39019(11) 0.60751(14) 0.0267(4) Uani 1 1 d . . .
N3 N 0.64242(18) 0.38646(12) 0.68168(15) 0.0280(5) Uani 1 1 d . . .
H3N H 0.704(2) 0.3850(16) 0.666(2) 0.034 Uiso 1 1 d . . .
N4 N 0.80534(17) 0.38217(11) 0.84483(14) 0.0260(4) Uani 1 1 d . . .
N5 N 0.69065(16) 0.24243(11) 0.87240(14) 0.0260(4) Uani 1 1 d . . .
N6 N 0.65835(16) 0.38925(11) 0.95083(14) 0.0257(4) Uani 1 1 d . . .
C1 C 0.4206(2) 0.39106(13) 0.69389(17) 0.0254(5) Uani 1 1 d . . .
C2 C 0.2976(2) 0.39603(14) 0.68423(17) 0.0270(5) Uani 1 1 d . . .
C3 C 0.2349(2) 0.45214(15) 0.62265(18) 0.0330(6) Uani 1 1 d . . .
H3 H 0.2713 0.4880 0.5894 0.040 Uiso 1 1 calc R . .
C4 C 0.1202(2) 0.45572(18) 0.6098(2) 0.0418(7) Uani 1 1 d . . .
H4 H 0.0783 0.4954 0.5700 0.050 Uiso 1 1 calc R . .
C5 C 0.0660(2) 0.4013(2) 0.6549(2) 0.0481(8) Uani 1 1 d . . .
H5 H -0.0132 0.4028 0.6441 0.058 Uiso 1 1 calc R . .
C6 C 0.1270(2) 0.3454(2) 0.7152(2) 0.0461(7) Uani 1 1 d . . .
H6 H 0.0898 0.3079 0.7454 0.055 Uiso 1 1 calc R . .
C7 C 0.2428(2) 0.34367(17) 0.73184(19) 0.0361(6) Uani 1 1 d . . .
H7 H 0.2849 0.3065 0.7760 0.043 Uiso 1 1 calc R . .
C8 C 0.5562(2) 0.38800(13) 0.60486(17) 0.0252(5) Uani 1 1 d . . .
C9 C 0.5761(2) 0.38571(14) 0.50457(17) 0.0266(5) Uani 1 1 d . . .
C10 C 0.4954(2) 0.41686(14) 0.42632(17) 0.0292(5) Uani 1 1 d . . .
H10 H 0.4314 0.4422 0.4380 0.035 Uiso 1 1 calc R . .
C11 C 0.5080(2) 0.41108(16) 0.33194(19) 0.0357(6) Uani 1 1 d . . .
H11 H 0.4530 0.4328 0.2792 0.043 Uiso 1 1 calc R . .
C12 C 0.6005(3) 0.37376(17) 0.31417(19) 0.0403(7) Uani 1 1 d . . .
H12 H 0.6081 0.3685 0.2491 0.048 Uiso 1 1 calc R . .
C13 C 0.6821(2) 0.34404(17) 0.3915(2) 0.0400(7) Uani 1 1 d . . .
H13 H 0.7464 0.3193 0.3796 0.048 Uiso 1 1 calc R . .
C14 C 0.6701(2) 0.35021(16) 0.48590(19) 0.0324(6) Uani 1 1 d . . .
H14 H 0.7267 0.3300 0.5386 0.039 Uiso 1 1 calc R . .
C15 C 0.8612(2) 0.45046(16) 0.85665(18) 0.0331(6) Uani 1 1 d . . .
H15 H 0.8200 0.4975 0.8405 0.040 Uiso 1 1 calc R . .
C16 C 0.9760(2) 0.45459(17) 0.8914(2) 0.0382(6) Uani 1 1 d . . .
H16 H 1.0134 0.5035 0.8972 0.046 Uiso 1 1 calc R . .
C17 C 1.0354(2) 0.38634(18) 0.9177(2) 0.0408(7) Uani 1 1 d . . .
H17 H 1.1142 0.3875 0.9438 0.049 Uiso 1 1 calc R . .
C18 C 0.9782(2) 0.31637(17) 0.9053(2) 0.0376(6) Uani 1 1 d . . .
H18 H 1.0179 0.2689 0.9228 0.045 Uiso 1 1 calc R . .
C19 C 0.8633(2) 0.31498(15) 0.86732(18) 0.0297(5) Uani 1 1 d . . .
C20 C 0.7993(2) 0.23941(15) 0.8472(2) 0.0371(6) Uani 1 1 d . . .
H20A H 0.7868 0.2265 0.7770 0.045 Uiso 1 1 calc R . .
H20B H 0.8450 0.1972 0.8853 0.045 Uiso 1 1 calc R . .
C21 C 0.6138(2) 0.17664(15) 0.82768(19) 0.0319(6) Uani 1 1 d . . .
C22 C 0.5810(2) 0.18688(17) 0.71630(19) 0.0388(6) Uani 1 1 d . . .
H22A H 0.5428 0.2370 0.6998 0.058 Uiso 1 1 calc R . .
H22B H 0.5308 0.1444 0.6865 0.058 Uiso 1 1 calc R . .
H22C H 0.6485 0.1858 0.6914 0.058 Uiso 1 1 calc R . .
C23 C 0.6696(3) 0.09662(16) 0.8538(2) 0.0407(7) Uani 1 1 d . . .
H23A H 0.7309 0.0906 0.8215 0.061 Uiso 1 1 calc R . .
H23B H 0.6142 0.0553 0.8317 0.061 Uiso 1 1 calc R . .
H23C H 0.6993 0.0930 0.9248 0.061 Uiso 1 1 calc R . .
C24 C 0.5064(2) 0.18129(17) 0.8632(2) 0.0412(7) Uani 1 1 d . . .
H24A H 0.5224 0.1657 0.9321 0.062 Uiso 1 1 calc R . .
H24B H 0.4500 0.1462 0.8240 0.062 Uiso 1 1 calc R . .
H24C H 0.4780 0.2349 0.8563 0.062 Uiso 1 1 calc R . .
C25 C 0.7094(2) 0.25023(15) 0.97879(18) 0.0348(6) Uani 1 1 d . . .
H25A H 0.7822 0.2259 1.0106 0.042 Uiso 1 1 calc R . .
H25B H 0.6502 0.2210 0.9999 0.042 Uiso 1 1 calc R . .
C26 C 0.70953(19) 0.33353(14) 1.01395(17) 0.0258(5) Uani 1 1 d . . .
C27 C 0.7580(2) 0.35160(17) 1.11083(18) 0.0330(6) Uani 1 1 d . . .
H27 H 0.7945 0.3121 1.1543 0.040 Uiso 1 1 calc R . .
C28 C 0.7533(2) 0.42683(17) 1.14432(19) 0.0374(6) Uani 1 1 d . . .
H28 H 0.7886 0.4399 1.2101 0.045 Uiso 1 1 calc R . .
C29 C 0.6964(2) 0.48304(16) 1.0805(2) 0.0376(6) Uani 1 1 d . . .
H29 H 0.6894 0.5349 1.1020 0.045 Uiso 1 1 calc R . .
C30 C 0.6500(2) 0.46172(15) 0.98486(19) 0.0326(6) Uani 1 1 d . . .
H30 H 0.6104 0.5000 0.9410 0.039 Uiso 1 1 calc R . .
Cl1 Cl 0.62840(6) 0.67502(4) 0.93164(5) 0.04331(18) Uani 1 1 d . . .
O1 O 0.7030(2) 0.62823(15) 0.8914(2) 0.0698(7) Uani 1 1 d . . .
O2 O 0.52596(18) 0.63371(15) 0.91793(18) 0.0639(7) Uani 1 1 d . . .
O3 O 0.6126(2) 0.74789(14) 0.8803(2) 0.0823(9) Uani 1 1 d . . .
O4 O 0.6792(3) 0.68590(17) 1.03217(19) 0.0944(11) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Ni1 0.02511(17) 0.02969(18) 0.01898(16) 0.00147(12) 0.00341(12) 0.00417(13)
N1 0.0288(11) 0.0346(12) 0.0197(10) 0.0010(9) 0.0072(8) 0.0061(9)
N2 0.0290(10) 0.0291(11) 0.0214(10) 0.0008(8) 0.0052(8) 0.0014(8)
N3 0.0245(10) 0.0375(12) 0.0230(10) 0.0029(9) 0.0076(8) 0.0030(9)
N4 0.0278(10) 0.0290(11) 0.0205(10) 0.0004(8) 0.0048(8) 0.0014(9)
N5 0.0277(10) 0.0246(10) 0.0242(10) -0.0009(8) 0.0038(8) 0.0012(8)
N6 0.0254(10) 0.0288(11) 0.0232(10) -0.0010(8) 0.0066(8) 0.0013(8)
C1 0.0285(12) 0.0220(12) 0.0247(12) 0.0012(9) 0.0048(10) 0.0022(9)
C2 0.0291(12) 0.0310(13) 0.0194(11) -0.0075(9) 0.0032(9) 0.0014(10)
C3 0.0347(13) 0.0324(14) 0.0284(13) -0.0040(11) 0.0010(11) 0.0021(11)
C4 0.0353(14) 0.0469(17) 0.0366(15) -0.0071(13) -0.0036(12) 0.0108(13)
C5 0.0269(14) 0.069(2) 0.0473(18) -0.0147(16) 0.0060(13) 0.0044(14)
C6 0.0386(16) 0.060(2) 0.0441(17) -0.0045(15) 0.0186(13) -0.0058(15)
C7 0.0378(15) 0.0414(16) 0.0312(14) -0.0001(12) 0.0123(12) 0.0030(12)
C8 0.0300(12) 0.0222(12) 0.0228(12) 0.0011(9) 0.0057(10) 0.0013(10)
C9 0.0327(13) 0.0247(12) 0.0226(12) -0.0033(9) 0.0069(10) -0.0056(10)
C10 0.0331(13) 0.0273(13) 0.0259(12) -0.0003(10) 0.0048(10) -0.0069(10)
C11 0.0442(16) 0.0356(14) 0.0247(13) 0.0014(11) 0.0039(11) -0.0143(12)
C12 0.0537(17) 0.0466(17) 0.0253(14) -0.0053(12) 0.0185(13) -0.0186(14)
C13 0.0429(16) 0.0412(16) 0.0417(16) -0.0101(13) 0.0213(13) -0.0100(13)
C14 0.0343(13) 0.0323(14) 0.0312(14) -0.0003(11) 0.0092(11) -0.0028(11)
C15 0.0359(14) 0.0324(14) 0.0303(14) 0.0051(11) 0.0070(11) 0.0019(11)
C16 0.0355(14) 0.0407(16) 0.0392(15) -0.0016(12) 0.0107(12) -0.0082(12)
C17 0.0280(13) 0.0536(18) 0.0381(16) -0.0013(13) 0.0034(12) -0.0008(13)
C18 0.0293(13) 0.0396(16) 0.0423(16) 0.0028(12) 0.0060(12) 0.0066(12)
C19 0.0304(13) 0.0306(14) 0.0280(13) -0.0020(10) 0.0068(10) 0.0035(10)
C20 0.0331(14) 0.0288(14) 0.0475(17) -0.0048(12) 0.0065(12) 0.0031(11)
C21 0.0338(13) 0.0299(13) 0.0298(13) -0.0024(11) 0.0039(11) -0.0017(11)
C22 0.0412(15) 0.0395(16) 0.0313(14) -0.0041(12) 0.0005(12) -0.0037(12)
C23 0.0490(17) 0.0283(14) 0.0401(16) -0.0013(12) 0.0024(13) -0.0023(12)
C24 0.0365(15) 0.0442(17) 0.0425(16) 0.0011(13) 0.0092(12) -0.0043(13)
C25 0.0490(16) 0.0276(14) 0.0239(13) 0.0020(10) 0.0016(11) 0.0042(12)
C26 0.0234(11) 0.0313(13) 0.0224(12) 0.0011(10) 0.0052(9) -0.0003(10)
C27 0.0313(13) 0.0436(15) 0.0224(12) 0.0023(11) 0.0034(10) -0.0028(12)
C28 0.0366(14) 0.0501(17) 0.0245(13) -0.0103(12) 0.0061(11) -0.0089(13)
C29 0.0402(15) 0.0357(15) 0.0385(15) -0.0128(12) 0.0129(12) -0.0056(12)
C30 0.0363(14) 0.0302(14) 0.0334(14) -0.0008(11) 0.0129(11) 0.0038(11)
Cl1 0.0421(4) 0.0394(4) 0.0403(4) 0.0005(3) -0.0051(3) -0.0004(3)
O1 0.0543(14) 0.0794(18) 0.0851(19) 0.0170(14) 0.0349(14) 0.0103(13)
O2 0.0358(12) 0.0833(18) 0.0734(17) 0.0192(13) 0.0150(11) -0.0061(11)
O3 0.0829(18) 0.0458(14) 0.092(2) 0.0170(13) -0.0279(15) -0.0008(13)
O4 0.133(3) 0.0755(19) 0.0464(15) -0.0165(13) -0.0304(16) 0.0196(18)

_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

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 1.836(2) . yes
Ni1 N1 1.840(2) . yes
Ni1 N4 1.926(2) . yes
Ni1 N6 1.930(2) . yes
N1 C1 1.316(3) . ?
N1 H1N 0.80(3) . ?
N2 C8 1.337(3) . ?
N2 C1 1.347(3) . ?
N3 C8 1.317(3) . ?
N3 H3N 0.84(3) . ?
N4 C15 1.347(3) . ?
N4 C19 1.351(3) . ?
N5 C25 1.468(3) . ?
N5 C20 1.469(3) . ?
N5 C21 1.507(3) . ?
N6 C30 1.345(3) . ?
N6 C26 1.351(3) . ?
C1 C2 1.490(3) . ?
C2 C7 1.392(4) . ?
C2 C3 1.394(3) . ?
C3 C4 1.381(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.391(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.375(5) . ?
C5 H5 0.9500 . ?
C6 C7 1.389(4) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C8 C9 1.496(3) . ?
C9 C14 1.390(4) . ?
C9 C10 1.397(3) . ?
C10 C11 1.383(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.383(4) . ?
C11 H11 0.9500 . ?
C12 C13 1.385(4) . ?
C12 H12 0.9500 . ?
C13 C14 1.380(4) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C15 C16 1.380(4) . ?
C15 H15 0.9500 . ?
C16 C17 1.382(4) . ?
C16 H16 0.9500 . ?
C17 C18 1.380(4) . ?
C17 H17 0.9500 . ?
C18 C19 1.385(3) . ?
C18 H18 0.9500 . ?
C19 C20 1.507(4) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 C24 1.530(4) . ?
C21 C22 1.534(4) . ?
C21 C23 1.537(4) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C25 C26 1.511(3) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C26 C27 1.385(3) . ?
C27 C28 1.379(4) . ?
C27 H27 0.9500 . ?
C28 C29 1.386(4) . ?
C28 H28 0.9500 . ?
C29 C30 1.378(4) . ?
C29 H29 0.9500 . ?
C30 H30 0.9500 . ?
Cl1 O4 1.414(2) . ?
Cl1 O2 1.418(2) . ?
Cl1 O3 1.433(2) . ?
Cl1 O1 1.439(3) . ?

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 N1 90.20(9) . . yes
N3 Ni1 N4 89.78(9) . . yes
N1 Ni1 N4 176.27(9) . . yes
N3 Ni1 N6 171.49(9) . . yes
N1 Ni1 N6 93.83(9) . . yes
N4 Ni1 N6 85.71(8) . . yes
C1 N1 Ni1 128.40(18) . . ?
C1 N1 H1N 112(2) . . ?
Ni1 N1 H1N 120(2) . . ?
C8 N2 C1 120.3(2) . . ?
C8 N3 Ni1 129.22(18) . . ?
C8 N3 H3N 112.2(19) . . ?
Ni1 N3 H3N 118.4(19) . . ?
C15 N4 C19 119.2(2) . . ?
C15 N4 Ni1 120.33(17) . . ?
C19 N4 Ni1 120.07(17) . . ?
C25 N5 C20 109.2(2) . . ?
C25 N5 C21 114.8(2) . . ?
C20 N5 C21 112.84(19) . . ?
C30 N6 C26 118.8(2) . . ?
C30 N6 Ni1 115.84(17) . . ?
C26 N6 Ni1 121.83(16) . . ?
N1 C1 N2 126.2(2) . . ?
N1 C1 C2 120.2(2) . . ?
N2 C1 C2 113.6(2) . . ?
C7 C2 C3 119.1(2) . . ?
C7 C2 C1 121.5(2) . . ?
C3 C2 C1 119.3(2) . . ?
C4 C3 C2 120.2(3) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C3 C4 C5 120.2(3) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
C6 C5 C4 119.9(3) . . ?
C6 C5 H5 120.0 . . ?
C4 C5 H5 120.0 . . ?
C5 C6 C7 120.1(3) . . ?
C5 C6 H6 119.9 . . ?
C7 C6 H6 119.9 . . ?
C6 C7 C2 120.3(3) . . ?
C6 C7 H7 119.8 . . ?
C2 C7 H7 119.8 . . ?
N3 C8 N2 125.6(2) . . ?
N3 C8 C9 119.4(2) . . ?
N2 C8 C9 115.1(2) . . ?
C14 C9 C10 118.8(2) . . ?
C14 C9 C8 122.0(2) . . ?
C10 C9 C8 119.1(2) . . ?
C11 C10 C9 120.4(2) . . ?
C11 C10 H10 119.8 . . ?
C9 C10 H10 119.8 . . ?
C10 C11 C12 120.2(3) . . ?
C10 C11 H11 119.9 . . ?
C12 C11 H11 119.9 . . ?
C11 C12 C13 119.8(2) . . ?
C11 C12 H12 120.1 . . ?
C13 C12 H12 120.1 . . ?
C14 C13 C12 120.2(3) . . ?
C14 C13 H13 119.9 . . ?
C12 C13 H13 119.9 . . ?
C13 C14 C9 120.6(3) . . ?
C13 C14 H14 119.7 . . ?
C9 C14 H14 119.7 . . ?
N4 C15 C16 122.4(2) . . ?
N4 C15 H15 118.8 . . ?
C16 C15 H15 118.8 . . ?
C15 C16 C17 118.8(3) . . ?
C15 C16 H16 120.6 . . ?
C17 C16 H16 120.6 . . ?
C18 C17 C16 118.8(3) . . ?
C18 C17 H17 120.6 . . ?
C16 C17 H17 120.6 . . ?
C17 C18 C19 120.4(3) . . ?
C17 C18 H18 119.8 . . ?
C19 C18 H18 119.8 . . ?
N4 C19 C18 120.5(2) . . ?
N4 C19 C20 117.8(2) . . ?
C18 C19 C20 121.7(2) . . ?
N5 C20 C19 113.0(2) . . ?
N5 C20 H20A 109.0 . . ?
C19 C20 H20A 109.0 . . ?
N5 C20 H20B 109.0 . . ?
C19 C20 H20B 109.0 . . ?
H20A C20 H20B 107.8 . . ?
N5 C21 C24 109.2(2) . . ?
N5 C21 C22 108.8(2) . . ?
C24 C21 C22 107.5(2) . . ?
N5 C21 C23 111.7(2) . . ?
C24 C21 C23 109.9(2) . . ?
C22 C21 C23 109.7(2) . . ?
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 . . ?
C21 C23 H23A 109.5 . . ?
C21 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C21 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C21 C24 H24A 109.5 . . ?
C21 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C21 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
N5 C25 C26 114.1(2) . . ?
N5 C25 H25A 108.7 . . ?
C26 C25 H25A 108.7 . . ?
N5 C25 H25B 108.7 . . ?
C26 C25 H25B 108.7 . . ?
H25A C25 H25B 107.6 . . ?
N6 C26 C27 120.7(2) . . ?
N6 C26 C25 119.3(2) . . ?
C27 C26 C25 120.0(2) . . ?
C28 C27 C26 120.2(2) . . ?
C28 C27 H27 119.9 . . ?
C26 C27 H27 119.9 . . ?
C27 C28 C29 119.0(2) . . ?
C27 C28 H28 120.5 . . ?
C29 C28 H28 120.5 . . ?
C30 C29 C28 118.2(2) . . ?
C30 C29 H29 120.9 . . ?
C28 C29 H29 120.9 . . ?
N6 C30 C29 123.0(2) . . ?
N6 C30 H30 118.5 . . ?
C29 C30 H30 118.5 . . ?
O4 Cl1 O2 111.15(19) . . ?
O4 Cl1 O3 111.32(17) . . ?
O2 Cl1 O3 111.16(15) . . ?
O4 Cl1 O1 107.57(18) . . ?
O2 Cl1 O1 107.60(16) . . ?
O3 Cl1 O1 107.85(18) . . ?
#---END