# Supplementary Material (ESI) for Chemical Communications
# This journal is © The Royal Society of Chemistry 2005



data_global

_journal_coden_Cambridge         182

loop_
_publ_author_name
'Robert Waymouth'
'Benjamin E. Ketz'
'Xavier G. Ottenwaelder'

_publ_contact_author_name        'Robert Waymouth'
_publ_contact_author_address     
;
Department of Chemistry
Stanford University
Stanford
CA
94305-5080
UNITED STATES OF AMERICA
;

_publ_contact_author_email       WAYMOUTH@LELAND.STANFORD.EDU

_publ_requested_journal          'Chemical Communications'

_publ_section_title              
;
Synthesis, Structure, and Olefin Polymerization with
Nickel(II) N-Heterocyclic Carbene Enolates
;

data_shelxl
_database_code_depnum_ccdc_archive 'CCDC 280713'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C31 H29 N3 Ni O'
_chemical_formula_sum            'C31 H29 N3 Ni O'
_chemical_formula_weight         518.28

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'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.7416(13)
_cell_length_b                   9.9127(14)
_cell_length_c                   13.6530(19)
_cell_angle_alpha                81.520(2)
_cell_angle_beta                 85.137(2)
_cell_angle_gamma                88.411(2)
_cell_volume                     1299.1(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    150
_cell_measurement_reflns_used    2392
_cell_measurement_theta_min      4.15
_cell_measurement_theta_max      24.39

_exptl_crystal_description       rhombic
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.14
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.325
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             544
_exptl_absorpt_coefficient_mu    0.775
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.71
_exptl_absorpt_correction_T_max  0.9
_exptl_absorpt_process_details   'Bruker AXS XPREP, SHELXTL v6.1 (2003)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      150
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         'not measured'
_diffrn_standards_interval_count 'not measured'
_diffrn_standards_interval_time  'not measured'
_diffrn_standards_decay_%        'not measured'
_diffrn_reflns_number            6591
_diffrn_reflns_av_R_equivalents  0.0582
_diffrn_reflns_av_sigmaI/netI    0.0853
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         4.15
_diffrn_reflns_theta_max         24.74
_reflns_number_total             4231
_reflns_number_gt                2942
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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     
'w=1/[\s^2^(Fo^2^)+(0.0500P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4231
_refine_ls_number_parameters     316
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0681
_refine_ls_R_factor_gt           0.0440
_refine_ls_wR_factor_ref         0.1027
_refine_ls_wR_factor_gt          0.0974
_refine_ls_goodness_of_fit_ref   0.926
_refine_ls_restrained_S_all      0.926
_refine_ls_shift/su_max          0.000
_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 0.15988(4) 0.04475(4) 0.27788(3) 0.02597(15) Uani 1 1 d . . .
O1 O 0.0207(2) -0.0794(2) 0.33394(16) 0.0368(6) Uani 1 1 d . . .
N1 N -0.0402(3) 0.0364(3) 0.14013(19) 0.0305(7) Uani 1 1 d . . .
N2 N 0.0596(2) 0.2307(3) 0.10607(19) 0.0292(7) Uani 1 1 d . . .
N3 N 0.2577(2) -0.0270(3) 0.39231(19) 0.0259(6) Uani 1 1 d . . .
C1 C 0.0601(3) 0.1113(3) 0.1713(2) 0.0251(7) Uani 1 1 d . . .
C2 C -0.0350(3) 0.2277(4) 0.0355(2) 0.0366(9) Uani 1 1 d . . .
H2 H -0.0525 0.2966 -0.0162 0.044 Uiso 1 1 calc R . .
C3 C -0.0951(3) 0.1074(4) 0.0563(2) 0.0379(9) Uani 1 1 d . . .
H3 H -0.1622 0.0759 0.0211 0.045 Uiso 1 1 calc R . .
C4 C -0.0945(3) -0.0866(4) 0.1912(3) 0.0368(9) Uani 1 1 d . . .
H4 H -0.1497 -0.1372 0.1583 0.044 Uiso 1 1 calc R . .
C5 C -0.0699(3) -0.1344(4) 0.2862(3) 0.0336(8) Uani 1 1 d . . .
C6 C -0.1465(3) -0.2508(4) 0.3440(3) 0.0378(9) Uani 1 1 d . . .
C7 C -0.1002(4) -0.3129(4) 0.4329(3) 0.0459(10) Uani 1 1 d . . .
H7 H -0.0200 -0.2825 0.4544 0.055 Uiso 1 1 calc R . .
C8 C -0.1713(4) -0.4195(4) 0.4905(3) 0.0579(12) Uani 1 1 d . . .
H8 H -0.1390 -0.4590 0.5504 0.069 Uiso 1 1 calc R . .
C9 C -0.2891(5) -0.4677(4) 0.4599(4) 0.0619(13) Uani 1 1 d . . .
H9 H -0.3366 -0.5394 0.4987 0.074 Uiso 1 1 calc R . .
C10 C -0.3355(4) -0.4080(5) 0.3713(4) 0.0611(13) Uani 1 1 d . . .
H10 H -0.4144 -0.4406 0.3496 0.073 Uiso 1 1 calc R . .
C11 C -0.2667(4) -0.3002(4) 0.3140(3) 0.0498(11) Uani 1 1 d . . .
H11 H -0.3008 -0.2600 0.2548 0.060 Uiso 1 1 calc R . .
C12 C 0.1220(3) 0.3566(3) 0.1194(2) 0.0299(8) Uani 1 1 d . . .
C13 C 0.0673(4) 0.4223(3) 0.1980(2) 0.0345(8) Uani 1 1 d . . .
C14 C 0.1288(4) 0.5432(4) 0.2103(3) 0.0422(10) Uani 1 1 d . . .
H14 H 0.0941 0.5890 0.2620 0.051 Uiso 1 1 calc R . .
C15 C 0.2393(4) 0.5977(4) 0.1484(3) 0.0403(9) Uani 1 1 d . . .
C16 C 0.2870(3) 0.5310(3) 0.0700(2) 0.0348(8) Uani 1 1 d . . .
H16 H 0.3606 0.5672 0.0273 0.042 Uiso 1 1 calc R . .
C17 C 0.2282(3) 0.4108(3) 0.0531(2) 0.0283(8) Uani 1 1 d . . .
C18 C -0.0503(4) 0.3640(4) 0.2692(3) 0.0513(11) Uani 1 1 d . . .
H18A H -0.1193 0.3313 0.2327 0.077 Uiso 1 1 calc R . .
H18B H -0.0897 0.4337 0.3054 0.077 Uiso 1 1 calc R . .
H18C H -0.0168 0.2899 0.3149 0.077 Uiso 1 1 calc R . .
C19 C 0.3051(5) 0.7260(4) 0.1661(3) 0.0638(13) Uani 1 1 d . . .
H19A H 0.2348 0.7898 0.1841 0.096 Uiso 1 1 calc R . .
H19B H 0.3576 0.7653 0.1065 0.096 Uiso 1 1 calc R . .
H19C H 0.3649 0.7052 0.2188 0.096 Uiso 1 1 calc R . .
C20 C 0.2802(4) 0.3445(4) -0.0360(2) 0.0401(9) Uani 1 1 d . . .
H20A H 0.2880 0.2477 -0.0166 0.060 Uiso 1 1 calc R . .
H20B H 0.3689 0.3801 -0.0614 0.060 Uiso 1 1 calc R . .
H20C H 0.2168 0.3636 -0.0866 0.060 Uiso 1 1 calc R . .
C21 C 0.3162(2) 0.1491(2) 0.22631(18) 0.0349(9) Uani 1 1 d G . .
C22 C 0.3527(3) 0.2613(2) 0.2681(2) 0.0694(15) Uani 1 1 d G . .
H22 H 0.2938 0.2935 0.3170 0.083 Uiso 1 1 calc R . .
C23 C 0.4771(4) 0.3255(3) 0.2366(3) 0.136(4) Uani 1 1 d G . .
H23 H 0.5015 0.4006 0.2646 0.163 Uiso 1 1 calc R . .
C24 C 0.5651(3) 0.2774(4) 0.1634(3) 0.163(5) Uani 1 1 d G . .
H24 H 0.6483 0.3203 0.1424 0.195 Uiso 1 1 calc R . .
C25 C 0.5286(3) 0.1652(4) 0.1217(2) 0.119(3) Uani 1 1 d G . .
H25 H 0.5874 0.1330 0.0727 0.143 Uiso 1 1 calc R . .
C26 C 0.4041(3) 0.1010(3) 0.15312(19) 0.0617(13) Uani 1 1 d G . .
H26 H 0.3797 0.0260 0.1252 0.074 Uiso 1 1 calc R . .
C27 C 0.1977(3) -0.0190(3) 0.4834(2) 0.0339(8) Uani 1 1 d . . .
H27 H 0.1139 0.0277 0.4888 0.041 Uiso 1 1 calc R . .
C28 C 0.2539(4) -0.0763(4) 0.5696(3) 0.0423(9) Uani 1 1 d . . .
H28 H 0.2086 -0.0681 0.6313 0.051 Uiso 1 1 calc R . .
C29 C 0.3763(4) -0.1447(4) 0.5631(3) 0.0446(10) Uani 1 1 d . . .
H29 H 0.4159 -0.1846 0.6202 0.054 Uiso 1 1 calc R . .
C30 C 0.4409(4) -0.1542(4) 0.4703(3) 0.0403(9) Uani 1 1 d . . .
H30 H 0.5244 -0.2010 0.4640 0.048 Uiso 1 1 calc R . .
C31 C 0.3804(3) -0.0937(3) 0.3881(3) 0.0313(8) Uani 1 1 d . . .
H31 H 0.4259 -0.0986 0.3260 0.038 Uiso 1 1 calc R . .

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 0.0229(2) 0.0305(3) 0.0248(3) -0.00432(18) -0.00314(17) -0.00034(16)
O1 0.0276(13) 0.0522(16) 0.0318(14) -0.0079(12) -0.0028(11) -0.0143(11)
N1 0.0227(14) 0.0441(18) 0.0266(16) -0.0112(13) -0.0027(12) -0.0008(12)
N2 0.0251(15) 0.0378(18) 0.0258(16) -0.0074(13) -0.0059(12) 0.0051(12)
N3 0.0251(15) 0.0224(15) 0.0301(16) -0.0034(12) -0.0024(12) -0.0019(11)
C1 0.0205(17) 0.0275(19) 0.0278(19) -0.0088(15) 0.0021(14) 0.0033(13)
C2 0.0300(19) 0.055(3) 0.026(2) -0.0071(17) -0.0111(16) 0.0108(17)
C3 0.0304(19) 0.060(3) 0.026(2) -0.0136(18) -0.0093(16) 0.0031(18)
C4 0.0290(19) 0.047(2) 0.038(2) -0.0179(18) -0.0012(16) -0.0093(16)
C5 0.0222(18) 0.045(2) 0.036(2) -0.0160(17) 0.0072(15) -0.0017(15)
C6 0.033(2) 0.045(2) 0.037(2) -0.0203(18) 0.0126(17) -0.0110(16)
C7 0.045(2) 0.048(2) 0.044(2) -0.010(2) 0.0114(19) -0.0083(18)
C8 0.066(3) 0.050(3) 0.054(3) -0.009(2) 0.024(2) -0.010(2)
C9 0.069(3) 0.047(3) 0.069(3) -0.027(2) 0.040(3) -0.022(2)
C10 0.050(3) 0.066(3) 0.073(3) -0.040(3) 0.025(2) -0.030(2)
C11 0.042(2) 0.062(3) 0.048(2) -0.027(2) 0.0147(19) -0.018(2)
C12 0.0347(19) 0.0306(19) 0.0243(19) -0.0012(15) -0.0100(16) 0.0093(15)
C13 0.043(2) 0.034(2) 0.0259(19) -0.0040(16) -0.0065(16) 0.0148(16)
C14 0.066(3) 0.033(2) 0.028(2) -0.0072(17) -0.0070(19) 0.0201(19)
C15 0.059(3) 0.029(2) 0.033(2) -0.0027(17) -0.0138(19) 0.0083(18)
C16 0.042(2) 0.030(2) 0.030(2) 0.0063(16) -0.0100(16) 0.0072(16)
C17 0.0351(19) 0.0282(19) 0.0213(18) 0.0003(14) -0.0102(15) 0.0097(15)
C18 0.051(2) 0.054(3) 0.050(3) -0.018(2) 0.007(2) 0.013(2)
C19 0.103(4) 0.034(2) 0.056(3) -0.008(2) -0.015(3) -0.004(2)
C20 0.046(2) 0.042(2) 0.032(2) -0.0080(17) 0.0007(17) 0.0030(17)
C21 0.0313(19) 0.0245(19) 0.047(2) 0.0123(16) -0.0212(18) -0.0001(15)
C22 0.093(3) 0.032(2) 0.085(3) 0.024(2) -0.071(3) -0.022(2)
C23 0.186(7) 0.081(4) 0.136(6) 0.089(4) -0.139(6) -0.093(5)
C24 0.110(5) 0.208(9) 0.139(7) 0.150(6) -0.105(5) -0.113(6)
C25 0.034(3) 0.189(7) 0.099(5) 0.096(5) -0.003(3) -0.009(3)
C26 0.033(2) 0.075(3) 0.062(3) 0.033(2) 0.009(2) 0.001(2)
C27 0.0301(19) 0.041(2) 0.029(2) -0.0028(16) 0.0042(16) -0.0024(15)
C28 0.049(2) 0.047(2) 0.028(2) 0.0003(17) 0.0001(17) -0.0027(19)
C29 0.057(3) 0.043(2) 0.031(2) 0.0087(18) -0.0156(19) -0.0002(19)
C30 0.039(2) 0.037(2) 0.045(2) -0.0027(18) -0.0130(18) 0.0108(16)
C31 0.0301(19) 0.030(2) 0.034(2) -0.0073(16) -0.0007(15) 0.0011(15)

_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 C1 1.848(3) . ?
Ni1 C21 1.891(2) . ?
Ni1 O1 1.891(2) . ?
Ni1 N3 1.934(2) . ?
O1 C5 1.315(4) . ?
N1 C1 1.375(4) . ?
N1 C3 1.392(4) . ?
N1 C4 1.406(4) . ?
N2 C1 1.373(4) . ?
N2 C2 1.393(4) . ?
N2 C12 1.446(4) . ?
N3 C27 1.341(4) . ?
N3 C31 1.351(4) . ?
C2 C3 1.325(5) . ?
C2 H2 0.9300 . ?
C3 H3 0.9300 . ?
C4 C5 1.353(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.480(5) . ?
C6 C7 1.383(5) . ?
C6 C11 1.397(5) . ?
C7 C8 1.385(5) . ?
C7 H7 0.9300 . ?
C8 C9 1.374(6) . ?
C8 H8 0.9300 . ?
C9 C10 1.373(6) . ?
C9 H9 0.9300 . ?
C10 C11 1.381(6) . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?
C12 C17 1.381(5) . ?
C12 C13 1.396(4) . ?
C13 C14 1.392(5) . ?
C13 C18 1.508(5) . ?
C14 C15 1.381(5) . ?
C14 H14 0.9300 . ?
C15 C16 1.381(5) . ?
C15 C19 1.500(5) . ?
C16 C17 1.394(4) . ?
C16 H16 0.9300 . ?
C17 C20 1.510(4) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 C22 1.3900 . ?
C21 C26 1.3900 . ?
C22 C23 1.3900 . ?
C22 H22 0.9300 . ?
C23 C24 1.3900 . ?
C23 H23 0.9300 . ?
C24 C25 1.3900 . ?
C24 H24 0.9300 . ?
C25 C26 1.3900 . ?
C25 H25 0.9300 . ?
C26 H26 0.9300 . ?
C27 C28 1.378(5) . ?
C27 H27 0.9300 . ?
C28 C29 1.358(5) . ?
C28 H28 0.9300 . ?
C29 C30 1.380(5) . ?
C29 H29 0.9300 . ?
C30 C31 1.364(4) . ?
C30 H30 0.9300 . ?
C31 H31 0.9300 . ?

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
C1 Ni1 C21 93.17(12) . . ?
C1 Ni1 O1 92.56(12) . . ?
C21 Ni1 O1 172.19(10) . . ?
C1 Ni1 N3 177.79(13) . . ?
C21 Ni1 N3 88.91(10) . . ?
O1 Ni1 N3 85.43(10) . . ?
C5 O1 Ni1 126.9(2) . . ?
C1 N1 C3 110.7(3) . . ?
C1 N1 C4 125.8(3) . . ?
C3 N1 C4 123.1(3) . . ?
C1 N2 C2 111.6(3) . . ?
C1 N2 C12 125.5(2) . . ?
C2 N2 C12 121.4(3) . . ?
C27 N3 C31 116.2(3) . . ?
C27 N3 Ni1 119.0(2) . . ?
C31 N3 Ni1 124.7(2) . . ?
N2 C1 N1 103.1(2) . . ?
N2 C1 Ni1 134.6(2) . . ?
N1 C1 Ni1 122.2(2) . . ?
C3 C2 N2 106.6(3) . . ?
C3 C2 H2 126.7 . . ?
N2 C2 H2 126.7 . . ?
C2 C3 N1 108.0(3) . . ?
C2 C3 H3 126.0 . . ?
N1 C3 H3 126.0 . . ?
C5 C4 N1 122.7(3) . . ?
C5 C4 H4 118.6 . . ?
N1 C4 H4 118.6 . . ?
O1 C5 C4 122.7(3) . . ?
O1 C5 C6 115.7(3) . . ?
C4 C5 C6 121.6(3) . . ?
C7 C6 C11 117.7(4) . . ?
C7 C6 C5 119.4(3) . . ?
C11 C6 C5 122.9(4) . . ?
C6 C7 C8 121.1(4) . . ?
C6 C7 H7 119.5 . . ?
C8 C7 H7 119.5 . . ?
C9 C8 C7 120.7(4) . . ?
C9 C8 H8 119.6 . . ?
C7 C8 H8 119.6 . . ?
C10 C9 C8 118.9(4) . . ?
C10 C9 H9 120.6 . . ?
C8 C9 H9 120.6 . . ?
C9 C10 C11 121.0(4) . . ?
C9 C10 H10 119.5 . . ?
C11 C10 H10 119.5 . . ?
C10 C11 C6 120.7(4) . . ?
C10 C11 H11 119.6 . . ?
C6 C11 H11 119.6 . . ?
C17 C12 C13 122.3(3) . . ?
C17 C12 N2 119.9(3) . . ?
C13 C12 N2 117.7(3) . . ?
C14 C13 C12 117.1(3) . . ?
C14 C13 C18 120.7(3) . . ?
C12 C13 C18 122.1(3) . . ?
C15 C14 C13 122.5(3) . . ?
C15 C14 H14 118.8 . . ?
C13 C14 H14 118.8 . . ?
C14 C15 C16 118.2(3) . . ?
C14 C15 C19 120.8(3) . . ?
C16 C15 C19 121.1(4) . . ?
C15 C16 C17 121.9(3) . . ?
C15 C16 H16 119.0 . . ?
C17 C16 H16 119.0 . . ?
C12 C17 C16 117.9(3) . . ?
C12 C17 C20 122.1(3) . . ?
C16 C17 C20 120.0(3) . . ?
C13 C18 H18A 109.5 . . ?
C13 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C13 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C15 C19 H19A 109.5 . . ?
C15 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C15 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C17 C20 H20A 109.5 . . ?
C17 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C17 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C22 C21 C26 120.0 . . ?
C22 C21 Ni1 121.46(16) . . ?
C26 C21 Ni1 118.07(16) . . ?
C21 C22 C23 120.0 . . ?
C21 C22 H22 120.0 . . ?
C23 C22 H22 120.0 . . ?
C22 C23 C24 120.0 . . ?
C22 C23 H23 120.0 . . ?
C24 C23 H23 120.0 . . ?
C25 C24 C23 120.0 . . ?
C25 C24 H24 120.0 . . ?
C23 C24 H24 120.0 . . ?
C24 C25 C26 120.0 . . ?
C24 C25 H25 120.0 . . ?
C26 C25 H25 120.0 . . ?
C25 C26 C21 120.0 . . ?
C25 C26 H26 120.0 . . ?
C21 C26 H26 120.0 . . ?
N3 C27 C28 123.4(3) . . ?
N3 C27 H27 118.3 . . ?
C28 C27 H27 118.3 . . ?
C29 C28 C27 119.0(3) . . ?
C29 C28 H28 120.5 . . ?
C27 C28 H28 120.5 . . ?
C28 C29 C30 118.9(3) . . ?
C28 C29 H29 120.5 . . ?
C30 C29 H29 120.5 . . ?
C31 C30 C29 119.0(3) . . ?
C31 C30 H30 120.5 . . ?
C29 C30 H30 120.5 . . ?
N3 C31 C30 123.3(3) . . ?
N3 C31 H31 118.3 . . ?
C30 C31 H31 118.3 . . ?

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
C1 Ni1 O1 C5 27.3(3) . . . . ?
N3 Ni1 O1 C5 -153.6(3) . . . . ?
C21 Ni1 N3 C27 127.3(2) . . . . ?
O1 Ni1 N3 C27 -58.1(2) . . . . ?
C21 Ni1 N3 C31 -57.3(3) . . . . ?
O1 Ni1 N3 C31 117.3(3) . . . . ?
C2 N2 C1 N1 -1.7(3) . . . . ?
C12 N2 C1 N1 164.5(3) . . . . ?
C2 N2 C1 Ni1 177.9(2) . . . . ?
C12 N2 C1 Ni1 -15.9(5) . . . . ?
C3 N1 C1 N2 2.2(3) . . . . ?
C4 N1 C1 N2 -170.1(3) . . . . ?
C3 N1 C1 Ni1 -177.5(2) . . . . ?
C4 N1 C1 Ni1 10.3(4) . . . . ?
C21 Ni1 C1 N2 -28.4(3) . . . . ?
O1 Ni1 C1 N2 156.9(3) . . . . ?
C21 Ni1 C1 N1 151.1(2) . . . . ?
O1 Ni1 C1 N1 -23.6(2) . . . . ?
C1 N2 C2 C3 0.5(4) . . . . ?
C12 N2 C2 C3 -166.3(3) . . . . ?
N2 C2 C3 N1 0.9(4) . . . . ?
C1 N1 C3 C2 -2.0(4) . . . . ?
C4 N1 C3 C2 170.5(3) . . . . ?
C1 N1 C4 C5 11.4(5) . . . . ?
C3 N1 C4 C5 -160.0(3) . . . . ?
Ni1 O1 C5 C4 -14.7(4) . . . . ?
Ni1 O1 C5 C6 166.8(2) . . . . ?
N1 C4 C5 O1 -9.1(5) . . . . ?
N1 C4 C5 C6 169.4(3) . . . . ?
O1 C5 C6 C7 -14.0(5) . . . . ?
C4 C5 C6 C7 167.5(3) . . . . ?
O1 C5 C6 C11 164.5(3) . . . . ?
C4 C5 C6 C11 -14.0(5) . . . . ?
C11 C6 C7 C8 -0.5(5) . . . . ?
C5 C6 C7 C8 178.1(3) . . . . ?
C6 C7 C8 C9 0.8(6) . . . . ?
C7 C8 C9 C10 -0.1(6) . . . . ?
C8 C9 C10 C11 -0.9(6) . . . . ?
C9 C10 C11 C6 1.2(6) . . . . ?
C7 C6 C11 C10 -0.5(5) . . . . ?
C5 C6 C11 C10 -179.1(3) . . . . ?
C1 N2 C12 C17 117.4(3) . . . . ?
C2 N2 C12 C17 -77.7(4) . . . . ?
C1 N2 C12 C13 -65.3(4) . . . . ?
C2 N2 C12 C13 99.6(4) . . . . ?
C17 C12 C13 C14 -3.0(5) . . . . ?
N2 C12 C13 C14 179.8(3) . . . . ?
C17 C12 C13 C18 178.9(3) . . . . ?
N2 C12 C13 C18 1.6(5) . . . . ?
C12 C13 C14 C15 -0.1(5) . . . . ?
C18 C13 C14 C15 178.1(3) . . . . ?
C13 C14 C15 C16 2.0(5) . . . . ?
C13 C14 C15 C19 -178.2(3) . . . . ?
C14 C15 C16 C17 -0.8(5) . . . . ?
C19 C15 C16 C17 179.3(3) . . . . ?
C13 C12 C17 C16 4.1(5) . . . . ?
N2 C12 C17 C16 -178.7(3) . . . . ?
C13 C12 C17 C20 -175.6(3) . . . . ?
N2 C12 C17 C20 1.6(4) . . . . ?
C15 C16 C17 C12 -2.1(5) . . . . ?
C15 C16 C17 C20 177.6(3) . . . . ?
C1 Ni1 C21 C22 107.67(16) . . . . ?
N3 Ni1 C21 C22 -71.60(15) . . . . ?
C1 Ni1 C21 C26 -80.24(15) . . . . ?
N3 Ni1 C21 C26 100.49(14) . . . . ?
C26 C21 C22 C23 0.0 . . . . ?
Ni1 C21 C22 C23 171.93(17) . . . . ?
C21 C22 C23 C24 0.0 . . . . ?
C22 C23 C24 C25 0.0 . . . . ?
C23 C24 C25 C26 0.0 . . . . ?
C24 C25 C26 C21 0.0 . . . . ?
C22 C21 C26 C25 0.0 . . . . ?
Ni1 C21 C26 C25 -172.20(16) . . . . ?
C31 N3 C27 C28 -1.1(5) . . . . ?
Ni1 N3 C27 C28 174.8(3) . . . . ?
N3 C27 C28 C29 0.0(5) . . . . ?
C27 C28 C29 C30 0.3(5) . . . . ?
C28 C29 C30 C31 0.4(5) . . . . ?
C27 N3 C31 C30 1.9(5) . . . . ?
Ni1 N3 C31 C30 -173.7(2) . . . . ?
C29 C30 C31 N3 -1.6(5) . . . . ?

_diffrn_measured_fraction_theta_max 0.951
_diffrn_reflns_theta_full        24.74
_diffrn_measured_fraction_theta_full 0.951
_refine_diff_density_max         0.628
_refine_diff_density_min         -0.592
_refine_diff_density_rms         0.064