# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_afh403
_database_code_depnum_ccdc_archive 'CCDC 1414822'
_audit_update_record             
;
2015-07-23 deposited with the CCDC.
2015-11-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C32 H44 N2 Ni O2'
_chemical_formula_weight         547.40

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   10.2568(9)
_cell_length_b                   19.4457(18)
_cell_length_c                   15.3511(14)
_cell_angle_alpha                90
_cell_angle_beta                 107.5750(12)
_cell_angle_gamma                90
_cell_volume                     2918.9(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    88(2)
_cell_measurement_reflns_used    8292
_cell_measurement_theta_min      2.33
_cell_measurement_theta_max      27.96

_exptl_crystal_description       plate
_exptl_crystal_colour            red
_exptl_crystal_density_meas      not_measured
_exptl_crystal_density_method    not_measured
_exptl_crystal_density_diffrn    1.246
_exptl_crystal_F_000             1176
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.434
_exptl_crystal_size_mid          0.357
_exptl_crystal_size_min          0.066
_exptl_absorpt_coefficient_mu    0.695
_shelx_estimated_absorpt_T_min   0.752
_shelx_estimated_absorpt_T_max   0.956
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.7724
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'Bruker SADABS 2012/1'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      88(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker SMART APEX II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            35094
_diffrn_reflns_av_unetI/netI     0.0358
_diffrn_reflns_av_R_equivalents  0.0419
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.083
_diffrn_reflns_theta_max         28.333
_diffrn_reflns_theta_full        25.500
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             7204
_reflns_number_gt                5754
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'Bruker APEX2 2013.6-2, 2013'
_computing_cell_refinement       'Bruker SAINT 8.32b, 2012'
_computing_data_reduction        'Bruker SAINT 8.32b, 2012'
_computing_structure_solution    'Bruker SHELXTL 2013/1'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
;
A red crystal of approximate dimensions 0.066 x 0.357 x 0.434 mm was mounted on a glass
fiber and transferred to a Bruker SMART APEX II diffractometer.  The APEX2 program
package was used to determine the unit-cell parameters and for data collection (20
sec/frame scan time for a sphere of diffraction data).  The raw frame data was processed
using SAINT and SADABS to yield the reflection data file.  Subsequent calculations were
carried out using the SHELXTL program.  The diffraction symmetry was 2/m and the
systematic absences were consistent with the monoclinic space group P21/c that was later
determined to be correct. The structure was solved by direct methods and refined on F2 by
full-matrix least-squares techniques.  The analytical scattering factors for neutral atoms
were used throughout the analysis.  Hydrogen atoms were located from a difference-Fourier
map and refined (x,y,z and Uiso). At convergence, wR2 = 0.0794 and Goof = 1.033 for 510
variables refined against 7204 data (0.75), R1 = 0.0337 for those 5754 data with I > 2.0sigma(I).  
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0324P)²+1.5515P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         7204
_refine_ls_number_parameters     510
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0505
_refine_ls_R_factor_gt           0.0337
_refine_ls_wR_factor_ref         0.0794
_refine_ls_wR_factor_gt          0.0731
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_restrained_S_all      1.033
_refine_ls_shift/su_max          0.002
_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_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 0.38881(2) 0.13225(2) 0.95867(2) 0.01105(6) Uani 1 1 d . . . . .
O1 O 0.45104(11) 0.11874(6) 1.08215(7) 0.0139(2) Uani 1 1 d . . . . .
O2 O 0.47525(11) 0.21528(6) 0.97408(7) 0.0143(2) Uani 1 1 d . . . . .
N1 N 0.29262(13) 0.04853(7) 0.93747(9) 0.0130(3) Uani 1 1 d . . . . .
N2 N 0.31548(13) 0.14290(7) 0.83099(9) 0.0116(3) Uani 1 1 d . . . . .
C1 C 0.52039(15) 0.17510(8) 1.12390(10) 0.0117(3) Uani 1 1 d . . . . .
C2 C 0.53254(16) 0.22799(8) 1.06429(10) 0.0124(3) Uani 1 1 d . . . . .
C3 C 0.59836(17) 0.28935(9) 1.09768(11) 0.0145(3) Uani 1 1 d . . . . .
C4 C 0.65667(16) 0.29875(8) 1.19187(10) 0.0139(3) Uani 1 1 d . . . . .
C5 C 0.64386(16) 0.24551(8) 1.25013(10) 0.0133(3) Uani 1 1 d . . . . .
C6 C 0.57637(15) 0.18322(8) 1.21905(10) 0.0119(3) Uani 1 1 d . . . . .
C7 C 0.72832(18) 0.36613(9) 1.23181(11) 0.0183(3) Uani 1 1 d . . . . .
C8 C 0.7515(2) 0.41370(11) 1.15794(13) 0.0283(5) Uani 1 1 d . . . . .
C9 C 0.8688(2) 0.35090(11) 1.30107(13) 0.0256(4) Uani 1 1 d . . . . .
C10 C 0.6387(2) 0.40483(10) 1.27935(13) 0.0226(4) Uani 1 1 d . . . . .
C11 C 0.56255(16) 0.12615(8) 1.28493(10) 0.0133(3) Uani 1 1 d . . . . .
C12 C 0.6302(2) 0.14584(10) 1.38533(11) 0.0200(4) Uani 1 1 d . . . . .
C13 C 0.63148(19) 0.06038(9) 1.26582(12) 0.0187(4) Uani 1 1 d . . . . .
C14 C 0.41079(18) 0.11118(9) 1.27229(12) 0.0173(3) Uani 1 1 d . . . . .
C15 C 0.29409(17) -0.00014(9) 0.99998(11) 0.0162(3) Uani 1 1 d . . . . .
C16 C 0.21224(18) -0.05769(9) 0.97929(11) 0.0172(3) Uani 1 1 d . . . . .
C17 C 0.12116(16) -0.06731(8) 0.89173(11) 0.0136(3) Uani 1 1 d . . . . .
C18 C 0.12145(16) -0.01665(8) 0.82758(10) 0.0126(3) Uani 1 1 d . . . . .
C19 C 0.20909(15) 0.03918(8) 0.85104(10) 0.0117(3) Uani 1 1 d . . . . .
C20 C 0.22838(15) 0.09220(8) 0.78767(10) 0.0116(3) Uani 1 1 d . . . . .
C21 C 0.17470(16) 0.09044(8) 0.69333(10) 0.0130(3) Uani 1 1 d . . . . .
C22 C 0.21053(16) 0.14027(8) 0.63914(10) 0.0125(3) Uani 1 1 d . . . . .
C23 C 0.29762(16) 0.19279(8) 0.68543(11) 0.0137(3) Uani 1 1 d . . . . .
C24 C 0.34670(16) 0.19248(8) 0.78012(11) 0.0140(3) Uani 1 1 d . . . . .
C25 C 0.02557(16) -0.12908(8) 0.87093(10) 0.0150(3) Uani 1 1 d . . . . .
C26 C -0.0458(2) -0.13674(10) 0.76808(12) 0.0218(4) Uani 1 1 d . . . . .
C27 C 0.1058(2) -0.19531(9) 0.90455(14) 0.0240(4) Uani 1 1 d . . . . .
C28 C -0.08330(18) -0.11769(10) 0.91997(12) 0.0197(4) Uani 1 1 d . . . . .
C29 C 0.16442(17) 0.13359(9) 0.53471(10) 0.0152(3) Uani 1 1 d . . . . .
C30 C 0.1799(3) 0.20099(11) 0.48805(13) 0.0317(5) Uani 1 1 d . . . . .
C31 C 0.2538(3) 0.07849(14) 0.51017(14) 0.0414(6) Uani 1 1 d . . . . .
C32 C 0.0146(2) 0.11189(15) 0.49986(14) 0.0376(6) Uani 1 1 d . . . . .
H3A H 0.6065(19) 0.3256(10) 1.0557(13) 0.023(5) Uiso 1 1 d . . . . .
H5A H 0.6795(18) 0.2515(9) 1.3133(13) 0.013(4) Uiso 1 1 d . . . . .
H8A H 0.661(2) 0.4288(11) 1.1131(15) 0.033(6) Uiso 1 1 d . . . . .
H8B H 0.805(2) 0.3913(11) 1.1275(15) 0.029(6) Uiso 1 1 d . . . . .
H8C H 0.803(2) 0.4525(11) 1.1875(14) 0.029(5) Uiso 1 1 d . . . . .
H9A H 0.862(2) 0.3223(11) 1.3525(14) 0.030(6) Uiso 1 1 d . . . . .
H9B H 0.915(2) 0.3928(11) 1.3260(13) 0.023(5) Uiso 1 1 d . . . . .
H9C H 0.929(2) 0.3275(11) 1.2712(14) 0.031(6) Uiso 1 1 d . . . . .
H10A H 0.556(2) 0.4160(10) 1.2387(14) 0.023(5) Uiso 1 1 d . . . . .
H10B H 0.682(2) 0.4487(11) 1.3037(14) 0.031(6) Uiso 1 1 d . . . . .
H10C H 0.622(2) 0.3774(11) 1.3285(15) 0.033(6) Uiso 1 1 d . . . . .
H12A H 0.731(2) 0.1539(10) 1.3981(13) 0.024(5) Uiso 1 1 d . . . . .
H12B H 0.620(2) 0.1075(11) 1.4250(14) 0.028(5) Uiso 1 1 d . . . . .
H12C H 0.5858(19) 0.1865(10) 1.4027(13) 0.020(5) Uiso 1 1 d . . . . .
H13A H 0.731(2) 0.0682(10) 1.2791(13) 0.024(5) Uiso 1 1 d . . . . .
H13B H 0.5938(19) 0.0443(10) 1.2025(13) 0.021(5) Uiso 1 1 d . . . . .
H13C H 0.6206(19) 0.0241(10) 1.3049(14) 0.022(5) Uiso 1 1 d . . . . .
H14A H 0.4030(18) 0.0747(10) 1.3149(13) 0.018(5) Uiso 1 1 d . . . . .
H14B H 0.3634(19) 0.0975(10) 1.2110(14) 0.022(5) Uiso 1 1 d . . . . .
H14C H 0.3674(18) 0.1507(10) 1.2884(12) 0.014(5) Uiso 1 1 d . . . . .
H15A H 0.3530(18) 0.0084(9) 1.0576(12) 0.011(4) Uiso 1 1 d . . . . .
H16A H 0.219(2) -0.0914(11) 1.0229(14) 0.031(6) Uiso 1 1 d . . . . .
H18A H 0.0641(17) -0.0199(9) 0.7656(12) 0.011(4) Uiso 1 1 d . . . . .
H21A H 0.1176(17) 0.0532(9) 0.6646(12) 0.012(4) Uiso 1 1 d . . . . .
H23A H 0.3294(19) 0.2272(10) 0.6538(13) 0.022(5) Uiso 1 1 d . . . . .
H24A H 0.4076(18) 0.2278(9) 0.8137(12) 0.014(4) Uiso 1 1 d . . . . .
H26A H 0.024(2) -0.1448(10) 0.7343(14) 0.027(5) Uiso 1 1 d . . . . .
H26B H -0.103(2) -0.0972(11) 0.7426(14) 0.025(5) Uiso 1 1 d . . . . .
H26C H -0.101(2) -0.1781(11) 0.7578(14) 0.026(5) Uiso 1 1 d . . . . .
H27A H 0.177(2) -0.2023(12) 0.8745(15) 0.039(6) Uiso 1 1 d . . . . .
H27B H 0.043(2) -0.2348(11) 0.8911(14) 0.032(6) Uiso 1 1 d . . . . .
H27C H 0.147(2) -0.1938(11) 0.9696(16) 0.032(6) Uiso 1 1 d . . . . .
H28A H -0.040(2) -0.1158(10) 0.9851(15) 0.027(5) Uiso 1 1 d . . . . .
H28B H -0.153(2) -0.1540(11) 0.9057(13) 0.024(5) Uiso 1 1 d . . . . .
H28C H -0.133(2) -0.0737(11) 0.9013(13) 0.024(5) Uiso 1 1 d . . . . .
H30A H 0.145(2) 0.1959(11) 0.4247(16) 0.034(6) Uiso 1 1 d . . . . .
H30B H 0.275(3) 0.2146(14) 0.5027(18) 0.061(8) Uiso 1 1 d . . . . .
H30C H 0.121(3) 0.2354(14) 0.5023(18) 0.058(8) Uiso 1 1 d . . . . .
H31A H 0.228(2) 0.0737(11) 0.4438(16) 0.038(6) Uiso 1 1 d . . . . .
H31B H 0.246(3) 0.0314(15) 0.5382(19) 0.068(9) Uiso 1 1 d . . . . .
H31C H 0.341(3) 0.0953(13) 0.5264(17) 0.044(7) Uiso 1 1 d . . . . .
H32A H -0.011(2) 0.1070(12) 0.4341(16) 0.039(6) Uiso 1 1 d . . . . .
H32B H -0.049(3) 0.1471(18) 0.519(2) 0.096(12) Uiso 1 1 d . . . . .
H32C H 0.002(3) 0.0681(14) 0.5210(17) 0.051(8) Uiso 1 1 d . . . . .


_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 O2 1.8227(11) . ?
Ni1 O1 1.8273(11) . ?
Ni1 N1 1.8804(14) . ?
Ni1 N2 1.8868(13) . ?
O1 C1 1.3574(18) . ?
O2 C2 1.3538(18) . ?
N1 C15 1.345(2) . ?
N1 C19 1.3569(19) . ?
N2 C24 1.339(2) . ?
N2 C20 1.3614(19) . ?
C1 C2 1.407(2) . ?
C1 C6 1.408(2) . ?
C2 C3 1.390(2) . ?
C3 C4 1.400(2) . ?
C4 C5 1.400(2) . ?
C4 C7 1.536(2) . ?
C5 C6 1.405(2) . ?
C6 C11 1.537(2) . ?
C7 C10 1.533(2) . ?
C7 C8 1.537(2) . ?
C7 C9 1.539(3) . ?
C11 C13 1.532(2) . ?
C11 C12 1.535(2) . ?
C11 C14 1.537(2) . ?
C15 C16 1.377(2) . ?
C16 C17 1.399(2) . ?
C17 C18 1.393(2) . ?
C17 C25 1.522(2) . ?
C18 C19 1.386(2) . ?
C19 C20 1.471(2) . ?
C20 C21 1.386(2) . ?
C21 C22 1.397(2) . ?
C22 C23 1.401(2) . ?
C22 C29 1.534(2) . ?
C23 C24 1.387(2) . ?
C25 C27 1.532(2) . ?
C25 C26 1.534(2) . ?
C25 C28 1.540(2) . ?
C29 C30 1.525(2) . ?
C29 C32 1.526(3) . ?
C29 C31 1.529(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
O2 Ni1 O1 89.36(5) . . ?
O2 Ni1 N1 177.01(5) . . ?
O1 Ni1 N1 93.19(5) . . ?
O2 Ni1 N2 93.63(5) . . ?
O1 Ni1 N2 176.59(5) . . ?
N1 Ni1 N2 83.77(6) . . ?
C1 O1 Ni1 110.05(9) . . ?
C2 O2 Ni1 109.78(9) . . ?
C15 N1 C19 118.12(14) . . ?
C15 N1 Ni1 126.42(11) . . ?
C19 N1 Ni1 115.38(11) . . ?
C24 N2 C20 118.28(13) . . ?
C24 N2 Ni1 126.46(11) . . ?
C20 N2 Ni1 115.14(10) . . ?
O1 C1 C2 114.82(13) . . ?
O1 C1 C6 124.88(14) . . ?
C2 C1 C6 120.29(14) . . ?
O2 C2 C3 123.10(14) . . ?
O2 C2 C1 115.82(13) . . ?
C3 C2 C1 121.07(14) . . ?
C2 C3 C4 120.08(15) . . ?
C3 C4 C5 118.04(15) . . ?
C3 C4 C7 121.82(14) . . ?
C5 C4 C7 120.10(14) . . ?
C4 C5 C6 123.52(14) . . ?
C5 C6 C1 116.98(14) . . ?
C5 C6 C11 122.21(13) . . ?
C1 C6 C11 120.81(14) . . ?
C10 C7 C4 109.00(14) . . ?
C10 C7 C8 107.73(16) . . ?
C4 C7 C8 112.39(13) . . ?
C10 C7 C9 109.65(14) . . ?
C4 C7 C9 110.29(15) . . ?
C8 C7 C9 107.72(16) . . ?
C13 C11 C12 107.80(13) . . ?
C13 C11 C6 109.71(13) . . ?
C12 C11 C6 112.16(14) . . ?
C13 C11 C14 109.03(14) . . ?
C12 C11 C14 107.89(13) . . ?
C6 C11 C14 110.17(13) . . ?
N1 C15 C16 122.18(15) . . ?
C15 C16 C17 120.93(15) . . ?
C18 C17 C16 116.19(15) . . ?
C18 C17 C25 123.25(14) . . ?
C16 C17 C25 120.53(14) . . ?
C19 C18 C17 120.64(14) . . ?
N1 C19 C18 121.84(14) . . ?
N1 C19 C20 112.42(13) . . ?
C18 C19 C20 125.69(14) . . ?
N2 C20 C21 121.56(14) . . ?
N2 C20 C19 112.58(13) . . ?
C21 C20 C19 125.69(14) . . ?
C20 C21 C22 120.83(14) . . ?
C21 C22 C23 116.48(14) . . ?
C21 C22 C29 120.68(14) . . ?
C23 C22 C29 122.69(14) . . ?
C24 C23 C22 120.16(15) . . ?
N2 C24 C23 122.62(15) . . ?
C17 C25 C27 110.26(13) . . ?
C17 C25 C26 111.69(14) . . ?
C27 C25 C26 107.82(15) . . ?
C17 C25 C28 107.47(13) . . ?
C27 C25 C28 110.58(14) . . ?
C26 C25 C28 109.03(14) . . ?
C30 C29 C32 108.04(17) . . ?
C30 C29 C31 109.35(18) . . ?
C32 C29 C31 109.56(19) . . ?
C30 C29 C22 112.04(14) . . ?
C32 C29 C22 110.48(14) . . ?
C31 C29 C22 107.35(14) . . ?

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
O2 Ni1 O1 C1 3.41(10) . . . . ?
N1 Ni1 O1 C1 -175.02(10) . . . . ?
O1 Ni1 O2 C2 -3.77(10) . . . . ?
N2 Ni1 O2 C2 174.58(10) . . . . ?
O1 Ni1 N1 C15 -5.52(14) . . . . ?
N2 Ni1 N1 C15 176.04(14) . . . . ?
O1 Ni1 N1 C19 170.97(11) . . . . ?
N2 Ni1 N1 C19 -7.46(11) . . . . ?
O2 Ni1 N2 C24 9.15(14) . . . . ?
N1 Ni1 N2 C24 -172.35(14) . . . . ?
O2 Ni1 N2 C20 -174.79(11) . . . . ?
N1 Ni1 N2 C20 3.72(11) . . . . ?
Ni1 O1 C1 C2 -2.30(16) . . . . ?
Ni1 O1 C1 C6 176.88(12) . . . . ?
Ni1 O2 C2 C3 -175.89(13) . . . . ?
Ni1 O2 C2 C1 3.36(16) . . . . ?
O1 C1 C2 O2 -0.7(2) . . . . ?
C6 C1 C2 O2 -179.94(14) . . . . ?
O1 C1 C2 C3 178.55(14) . . . . ?
C6 C1 C2 C3 -0.7(2) . . . . ?
O2 C2 C3 C4 -179.31(14) . . . . ?
C1 C2 C3 C4 1.5(2) . . . . ?
C2 C3 C4 C5 -1.3(2) . . . . ?
C2 C3 C4 C7 -179.00(15) . . . . ?
C3 C4 C5 C6 0.3(2) . . . . ?
C7 C4 C5 C6 178.09(15) . . . . ?
C4 C5 C6 C1 0.4(2) . . . . ?
C4 C5 C6 C11 -179.21(14) . . . . ?
O1 C1 C6 C5 -179.41(14) . . . . ?
C2 C1 C6 C5 -0.3(2) . . . . ?
O1 C1 C6 C11 0.2(2) . . . . ?
C2 C1 C6 C11 179.38(14) . . . . ?
C3 C4 C7 C10 108.42(18) . . . . ?
C5 C4 C7 C10 -69.2(2) . . . . ?
C3 C4 C7 C8 -10.9(2) . . . . ?
C5 C4 C7 C8 171.40(16) . . . . ?
C3 C4 C7 C9 -131.15(17) . . . . ?
C5 C4 C7 C9 51.2(2) . . . . ?
C5 C6 C11 C13 -119.84(16) . . . . ?
C1 C6 C11 C13 60.53(19) . . . . ?
C5 C6 C11 C12 -0.1(2) . . . . ?
C1 C6 C11 C12 -179.70(14) . . . . ?
C5 C6 C11 C14 120.13(16) . . . . ?
C1 C6 C11 C14 -59.51(19) . . . . ?
C19 N1 C15 C16 -1.3(2) . . . . ?
Ni1 N1 C15 C16 175.12(13) . . . . ?
N1 C15 C16 C17 -1.3(3) . . . . ?
C15 C16 C17 C18 1.6(2) . . . . ?
C15 C16 C17 C25 -176.62(15) . . . . ?
C16 C17 C18 C19 0.6(2) . . . . ?
C25 C17 C18 C19 178.71(14) . . . . ?
C15 N1 C19 C18 3.5(2) . . . . ?
Ni1 N1 C19 C18 -173.29(12) . . . . ?
C15 N1 C19 C20 -173.82(14) . . . . ?
Ni1 N1 C19 C20 9.38(16) . . . . ?
C17 C18 C19 N1 -3.2(2) . . . . ?
C17 C18 C19 C20 173.77(15) . . . . ?
C24 N2 C20 C21 1.3(2) . . . . ?
Ni1 N2 C20 C21 -175.13(12) . . . . ?
C24 N2 C20 C19 176.77(13) . . . . ?
Ni1 N2 C20 C19 0.37(16) . . . . ?
N1 C19 C20 N2 -6.22(18) . . . . ?
C18 C19 C20 N2 176.57(14) . . . . ?
N1 C19 C20 C21 169.05(15) . . . . ?
C18 C19 C20 C21 -8.2(3) . . . . ?
N2 C20 C21 C22 1.2(2) . . . . ?
C19 C20 C21 C22 -173.63(15) . . . . ?
C20 C21 C22 C23 -2.7(2) . . . . ?
C20 C21 C22 C29 172.84(14) . . . . ?
C21 C22 C23 C24 1.8(2) . . . . ?
C29 C22 C23 C24 -173.67(15) . . . . ?
C20 N2 C24 C23 -2.3(2) . . . . ?
Ni1 N2 C24 C23 173.70(12) . . . . ?
C22 C23 C24 N2 0.7(2) . . . . ?
C18 C17 C25 C27 132.20(16) . . . . ?
C16 C17 C25 C27 -49.7(2) . . . . ?
C18 C17 C25 C26 12.3(2) . . . . ?
C16 C17 C25 C26 -169.59(16) . . . . ?
C18 C17 C25 C28 -107.20(17) . . . . ?
C16 C17 C25 C28 70.87(19) . . . . ?
C21 C22 C29 C30 164.50(17) . . . . ?
C23 C22 C29 C30 -20.3(2) . . . . ?
C21 C22 C29 C32 44.0(2) . . . . ?
C23 C22 C29 C32 -140.78(18) . . . . ?
C21 C22 C29 C31 -75.4(2) . . . . ?
C23 C22 C29 C31 99.8(2) . . . . ?

_refine_diff_density_max         0.550
_refine_diff_density_min         -0.301
_refine_diff_density_rms         0.059

_chemical_properties_physical    Moisture-sensitive
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_afh412
_database_code_depnum_ccdc_archive 'CCDC 1414823'
_audit_update_record             
;
2015-07-23 deposited with the CCDC.
2015-11-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C56 H73 N3 Ni O'
_chemical_formula_weight         862.88

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_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. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   15.7714(10)
_cell_length_b                   17.0164(11)
_cell_length_c                   18.6084(12)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4994.0(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    143(2)
_cell_measurement_reflns_used    9913
_cell_measurement_theta_min      2.49
_cell_measurement_theta_max      27.28

_exptl_crystal_description       prism
_exptl_crystal_colour            green
_exptl_crystal_density_meas      not_measured
_exptl_crystal_density_method    not_measured
_exptl_crystal_density_diffrn    1.148
_exptl_crystal_F_000             1864
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.328
_exptl_crystal_size_mid          0.236
_exptl_crystal_size_min          0.105
_exptl_absorpt_coefficient_mu    0.429
_shelx_estimated_absorpt_T_min   0.872
_shelx_estimated_absorpt_T_max   0.956
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.8437
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'Bruker SADABS 2012/1'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      143(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker SMART APEX II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            44108
_diffrn_reflns_av_unetI/netI     0.0488
_diffrn_reflns_av_R_equivalents  0.0449
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         1.622
_diffrn_reflns_theta_max         28.304
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.957
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             11901
_reflns_number_gt                10144
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.788
_reflns_Friedel_fraction_max     0.933
_reflns_Friedel_fraction_full    1.000

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'Bruker APEX2 2013.10-0, 2013'
_computing_cell_refinement       'Bruker SAINT 8.34a, 2013'
_computing_data_reduction        'Bruker SAINT 8.34a, 2013'
_computing_structure_solution    'Bruker SHELXTL 2013/1'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 ? 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0431P)²+0.2592P] where P=(Fo²+2Fc²)/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_abs_structure_details 
; 
 Flack x determined using 4036 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.005(5)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         11901
_refine_ls_number_parameters     566
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0531
_refine_ls_R_factor_gt           0.0387
_refine_ls_wR_factor_ref         0.0839
_refine_ls_wR_factor_gt          0.0789
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_restrained_S_all      1.024
_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_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 0.47209(2) 0.13093(2) 0.89198(2) 0.01516(8) Uani 1 1 d . . . . .
O1 O 0.44888(11) 0.02617(10) 0.88020(9) 0.0173(4) Uani 1 1 d . . . . .
N1 N 0.54772(13) 0.09910(12) 0.96353(11) 0.0172(5) Uani 1 1 d . . . . .
N2 N 0.39234(14) 0.15514(12) 0.81809(11) 0.0160(5) Uani 1 1 d . . . . .
N3 N 0.48251(13) 0.24454(12) 0.89605(11) 0.0169(4) Uani 1 1 d . . . . .
C1 C 0.48946(16) -0.02110(15) 0.92805(13) 0.0158(5) Uani 1 1 d . . . . .
C2 C 0.54645(16) 0.01820(15) 0.97356(13) 0.0155(5) Uani 1 1 d . . . . .
C3 C 0.59317(17) -0.02426(15) 1.02426(14) 0.0181(5) Uani 1 1 d . . . . .
H3A H 0.6348 0.0017 1.0525 0.022 Uiso 1 1 calc R U . . .
C4 C 0.57920(17) -0.10407(15) 1.03356(13) 0.0172(5) Uani 1 1 d . . . . .
C5 C 0.52345(17) -0.14191(15) 0.98721(12) 0.0174(5) Uani 1 1 d . . . . .
H5A H 0.5150 -0.1969 0.9926 0.021 Uiso 1 1 calc R U . . .
C6 C 0.47884(17) -0.10218(14) 0.93245(12) 0.0153(5) Uani 1 1 d . . . . .
C7 C 0.62325(16) -0.14624(15) 1.09654(13) 0.0200(6) Uani 1 1 d . . . . .
C8 C 0.5934(2) -0.10967(18) 1.16738(15) 0.0305(7) Uani 1 1 d . . . . .
H8A H 0.6206 -0.1368 1.2077 0.046 Uiso 1 1 calc R U . . .
H8B H 0.5317 -0.1149 1.1714 0.046 Uiso 1 1 calc R U . . .
H8C H 0.6088 -0.0539 1.1684 0.046 Uiso 1 1 calc R U . . .
C9 C 0.71969(17) -0.1369(2) 1.09012(15) 0.0301(7) Uani 1 1 d . . . . .
H9A H 0.7474 -0.1641 1.1302 0.045 Uiso 1 1 calc R U . . .
H9B H 0.7344 -0.0809 1.0915 0.045 Uiso 1 1 calc R U . . .
H9C H 0.7389 -0.1596 1.0446 0.045 Uiso 1 1 calc R U . . .
C10 C 0.60326(18) -0.23439(17) 1.09955(16) 0.0270(6) Uani 1 1 d . . . . .
H10A H 0.5421 -0.2418 1.1060 0.041 Uiso 1 1 calc R U . . .
H10B H 0.6337 -0.2583 1.1400 0.041 Uiso 1 1 calc R U . . .
H10C H 0.6212 -0.2594 1.0546 0.041 Uiso 1 1 calc R U . . .
C11 C 0.42214(16) -0.14649(15) 0.87925(13) 0.0182(6) Uani 1 1 d . . . . .
C12 C 0.45447(18) -0.13189(18) 0.80243(13) 0.0253(6) Uani 1 1 d . . . . .
H12A H 0.4537 -0.0754 0.7923 0.038 Uiso 1 1 calc R U . . .
H12B H 0.4177 -0.1592 0.7681 0.038 Uiso 1 1 calc R U . . .
H12C H 0.5126 -0.1517 0.7980 0.038 Uiso 1 1 calc R U . . .
C13 C 0.42262(19) -0.23572(16) 0.89151(18) 0.0301(6) Uani 1 1 d . . . . .
H13A H 0.4807 -0.2556 0.8871 0.045 Uiso 1 1 calc R U . . .
H13B H 0.3865 -0.2612 0.8556 0.045 Uiso 1 1 calc R U . . .
H13C H 0.4010 -0.2473 0.9397 0.045 Uiso 1 1 calc R U . . .
C14 C 0.33000(16) -0.11805(16) 0.88516(15) 0.0240(6) Uani 1 1 d . . . . .
H14A H 0.3275 -0.0616 0.8749 0.036 Uiso 1 1 calc R U . . .
H14B H 0.3090 -0.1278 0.9339 0.036 Uiso 1 1 calc R U . . .
H14C H 0.2948 -0.1466 0.8505 0.036 Uiso 1 1 calc R U . . .
C15 C 0.62109(16) 0.13916(16) 0.98842(13) 0.0181(5) Uani 1 1 d . . . . .
C16 C 0.62441(18) 0.16626(15) 1.06020(14) 0.0213(6) Uani 1 1 d . . . . .
C17 C 0.69462(19) 0.21029(17) 1.08125(16) 0.0277(7) Uani 1 1 d . . . . .
H17A H 0.6984 0.2284 1.1294 0.033 Uiso 1 1 calc R U . . .
C18 C 0.75888(19) 0.22809(18) 1.03359(17) 0.0319(7) Uani 1 1 d . . . . .
H18A H 0.8047 0.2605 1.0484 0.038 Uiso 1 1 calc R U . . .
C19 C 0.75666(19) 0.19895(18) 0.96436(16) 0.0301(7) Uani 1 1 d . . . . .
H19A H 0.8018 0.2104 0.9322 0.036 Uiso 1 1 calc R U . . .
C20 C 0.68896(18) 0.15302(16) 0.94129(15) 0.0229(6) Uani 1 1 d . . . . .
C21 C 0.55224(18) 0.14800(16) 1.11150(15) 0.0271(6) Uani 1 1 d . . . . .
H21A H 0.5300 0.0949 1.0982 0.033 Uiso 1 1 calc R U . . .
C22 C 0.4785(2) 0.20591(18) 1.10372(19) 0.0419(8) Uani 1 1 d . . . . .
H22A H 0.4990 0.2595 1.1120 0.063 Uiso 1 1 calc R U . . .
H22B H 0.4344 0.1932 1.1390 0.063 Uiso 1 1 calc R U . . .
H22C H 0.4548 0.2021 1.0551 0.063 Uiso 1 1 calc R U . . .
C23 C 0.5801(3) 0.1435(3) 1.18984(16) 0.0548(11) Uani 1 1 d . . . . .
H23A H 0.6271 0.1062 1.1944 0.082 Uiso 1 1 calc R U . . .
H23B H 0.5324 0.1259 1.2195 0.082 Uiso 1 1 calc R U . . .
H23C H 0.5987 0.1956 1.2059 0.082 Uiso 1 1 calc R U . . .
C24 C 0.69012(19) 0.11846(18) 0.86563(15) 0.0283(7) Uani 1 1 d . . . . .
H24A H 0.6358 0.0891 0.8589 0.034 Uiso 1 1 calc R U . . .
C25 C 0.6939(3) 0.1809(2) 0.80803(17) 0.0447(9) Uani 1 1 d . . . . .
H25A H 0.6921 0.1559 0.7606 0.067 Uiso 1 1 calc R U . . .
H25B H 0.7468 0.2108 0.8129 0.067 Uiso 1 1 calc R U . . .
H25C H 0.6455 0.2165 0.8132 0.067 Uiso 1 1 calc R U . . .
C26 C 0.7621(3) 0.0595(2) 0.8577(2) 0.0554(11) Uani 1 1 d . . . . .
H26A H 0.7606 0.0365 0.8094 0.083 Uiso 1 1 calc R U . . .
H26B H 0.7557 0.0178 0.8936 0.083 Uiso 1 1 calc R U . . .
H26C H 0.8165 0.0863 0.8650 0.083 Uiso 1 1 calc R U . . .
C27 C 0.34810(18) 0.10309(16) 0.77836(14) 0.0213(6) Uani 1 1 d . . . . .
H27A H 0.3529 0.0488 0.7894 0.026 Uiso 1 1 calc R U . . .
C28 C 0.29626(17) 0.12552(18) 0.72245(13) 0.0227(6) Uani 1 1 d . . . . .
H28A H 0.2658 0.0868 0.6962 0.027 Uiso 1 1 calc R U . . .
C29 C 0.28808(17) 0.20481(16) 0.70402(13) 0.0193(6) Uani 1 1 d . . . . .
C30 C 0.33252(16) 0.25804(16) 0.74562(13) 0.0185(6) Uani 1 1 d . . . . .
H30A H 0.3285 0.3127 0.7357 0.022 Uiso 1 1 calc R U . . .
C31 C 0.38316(16) 0.23180(15) 0.80196(12) 0.0154(5) Uani 1 1 d . . . . .
C32 C 0.43147(16) 0.28345(15) 0.84930(13) 0.0149(5) Uani 1 1 d . . . . .
C33 C 0.42416(16) 0.36454(16) 0.84846(12) 0.0178(5) Uani 1 1 d . . . . .
H33A H 0.3876 0.3887 0.8144 0.021 Uiso 1 1 calc R U . . .
C34 C 0.46916(17) 0.41129(14) 0.89634(14) 0.0183(5) Uani 1 1 d . . . . .
C35 C 0.52102(18) 0.37078(17) 0.94433(13) 0.0229(5) Uani 1 1 d . . . . .
H35A H 0.5530 0.3993 0.9788 0.027 Uiso 1 1 calc R U . . .
C36 C 0.52662(19) 0.28994(15) 0.94254(13) 0.0210(5) Uani 1 1 d . . . . .
H36A H 0.5634 0.2648 0.9758 0.025 Uiso 1 1 calc R U . . .
C37 C 0.23496(18) 0.22952(17) 0.63880(14) 0.0240(6) Uani 1 1 d . . . . .
C38 C 0.14326(19) 0.20098(19) 0.64886(17) 0.0342(7) Uani 1 1 d . . . . .
H38A H 0.1101 0.2135 0.6058 0.051 Uiso 1 1 calc R U . . .
H38B H 0.1181 0.2272 0.6906 0.051 Uiso 1 1 calc R U . . .
H38C H 0.1431 0.1440 0.6565 0.051 Uiso 1 1 calc R U . . .
C39 C 0.2733(2) 0.1903(2) 0.57221(15) 0.0350(8) Uani 1 1 d . . . . .
H39A H 0.2415 0.2063 0.5294 0.052 Uiso 1 1 calc R U . . .
H39B H 0.2704 0.1331 0.5775 0.052 Uiso 1 1 calc R U . . .
H39C H 0.3327 0.2064 0.5671 0.052 Uiso 1 1 calc R U . . .
C40 C 0.2349(2) 0.31853(18) 0.62762(16) 0.0345(8) Uani 1 1 d . . . . .
H40A H 0.2930 0.3367 0.6193 0.052 Uiso 1 1 calc R U . . .
H40B H 0.2119 0.3443 0.6705 0.052 Uiso 1 1 calc R U . . .
H40C H 0.1996 0.3316 0.5859 0.052 Uiso 1 1 calc R U . . .
C41 C 0.46005(19) 0.50045(15) 0.89932(16) 0.0246(6) Uani 1 1 d . . . . .
C42 C 0.5483(2) 0.53805(18) 0.9045(2) 0.0431(9) Uani 1 1 d . . . . .
H42A H 0.5427 0.5954 0.9046 0.065 Uiso 1 1 calc R U . . .
H42B H 0.5826 0.5217 0.8632 0.065 Uiso 1 1 calc R U . . .
H42C H 0.5759 0.5210 0.9490 0.065 Uiso 1 1 calc R U . . .
C43 C 0.4080(2) 0.5203(2) 0.96620(17) 0.0395(9) Uani 1 1 d . . . . .
H43A H 0.4004 0.5774 0.9694 0.059 Uiso 1 1 calc R U . . .
H43B H 0.4378 0.5015 1.0091 0.059 Uiso 1 1 calc R U . . .
H43C H 0.3524 0.4948 0.9630 0.059 Uiso 1 1 calc R U . . .
C44 C 0.4157(2) 0.53306(17) 0.83240(17) 0.0333(8) Uani 1 1 d . . . . .
H44A H 0.3586 0.5108 0.8289 0.050 Uiso 1 1 calc R U . . .
H44B H 0.4484 0.5189 0.7895 0.050 Uiso 1 1 calc R U . . .
H44C H 0.4119 0.5904 0.8360 0.050 Uiso 1 1 calc R U . . .
C45 C 0.1517(2) 0.0291(2) 0.8866(2) 0.0474(9) Uani 1 1 d . . . . .
H45A H 0.2075 0.0389 0.9036 0.057 Uiso 1 1 calc R U . . .
C46 C 0.1183(2) -0.0456(2) 0.8901(2) 0.0456(9) Uani 1 1 d . . . . .
H46A H 0.1511 -0.0875 0.9093 0.055 Uiso 1 1 calc R U . . .
C47 C 0.0374(2) -0.0594(2) 0.86562(18) 0.0432(9) Uani 1 1 d . . . . .
H47A H 0.0144 -0.1110 0.8678 0.052 Uiso 1 1 calc R U . . .
C48 C -0.0102(2) 0.0005(2) 0.83824(18) 0.0432(9) Uani 1 1 d . . . . .
H48A H -0.0660 -0.0095 0.8213 0.052 Uiso 1 1 calc R U . . .
C49 C 0.0225(3) 0.0747(2) 0.83515(17) 0.0440(9) Uani 1 1 d . . . . .
H49A H -0.0111 0.1164 0.8168 0.053 Uiso 1 1 calc R U . . .
C50 C 0.1038(3) 0.0893(2) 0.8584(2) 0.0484(9) Uani 1 1 d . . . . .
H50A H 0.1268 0.1408 0.8551 0.058 Uiso 1 1 calc R U . . .
C51 C 0.3252(2) 0.04194(19) 1.04887(16) 0.0301(7) Uani 1 1 d . . . . .
H51A H 0.3357 0.0317 0.9995 0.036 Uiso 1 1 calc R U . . .
C52 C 0.2567(2) 0.0875(2) 1.06926(19) 0.0372(8) Uani 1 1 d . . . . .
H52A H 0.2203 0.1089 1.0336 0.045 Uiso 1 1 calc R U . . .
C53 C 0.2407(2) 0.10198(19) 1.14087(19) 0.0390(8) Uani 1 1 d . . . . .
H53A H 0.1928 0.1324 1.1546 0.047 Uiso 1 1 calc R U . . .
C54 C 0.2944(2) 0.0723(2) 1.19242(18) 0.0391(8) Uani 1 1 d . . . . .
H54A H 0.2843 0.0832 1.2418 0.047 Uiso 1 1 calc R U . . .
C55 C 0.3633(2) 0.02644(19) 1.17240(18) 0.0356(8) Uani 1 1 d . . . . .
H55A H 0.4000 0.0054 1.2080 0.043 Uiso 1 1 calc R U . . .
C56 C 0.37827(18) 0.01157(17) 1.10069(18) 0.0297(7) Uani 1 1 d . . . . .
H56A H 0.4254 -0.0198 1.0869 0.036 Uiso 1 1 calc R U . . .


_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 O1 1.8329(17) . ?
Ni1 N1 1.868(2) . ?
Ni1 N2 1.908(2) . ?
Ni1 N3 1.942(2) . ?
O1 C1 1.360(3) . ?
N1 C2 1.389(3) . ?
N1 C15 1.421(3) . ?
N2 C31 1.346(3) . ?
N2 C27 1.348(3) . ?
N3 C36 1.353(3) . ?
N3 C32 1.358(3) . ?
C1 C6 1.392(3) . ?
C1 C2 1.404(3) . ?
C2 C3 1.398(3) . ?
C3 C4 1.387(4) . ?
C4 C5 1.390(4) . ?
C4 C7 1.540(3) . ?
C5 C6 1.411(3) . ?
C6 C11 1.532(3) . ?
C7 C8 1.532(4) . ?
C7 C10 1.534(4) . ?
C7 C9 1.534(4) . ?
C11 C13 1.535(4) . ?
C11 C14 1.536(4) . ?
C11 C12 1.538(3) . ?
C15 C20 1.404(4) . ?
C15 C16 1.414(4) . ?
C16 C17 1.393(4) . ?
C16 C21 1.518(4) . ?
C17 C18 1.380(4) . ?
C18 C19 1.381(4) . ?
C19 C20 1.391(4) . ?
C20 C24 1.526(4) . ?
C21 C23 1.524(4) . ?
C21 C22 1.532(4) . ?
C24 C25 1.510(4) . ?
C24 C26 1.522(5) . ?
C27 C28 1.377(4) . ?
C28 C29 1.398(4) . ?
C29 C30 1.382(4) . ?
C29 C37 1.533(4) . ?
C30 C31 1.392(3) . ?
C31 C32 1.459(3) . ?
C32 C33 1.385(4) . ?
C33 C34 1.390(4) . ?
C34 C35 1.393(4) . ?
C34 C41 1.525(3) . ?
C35 C36 1.379(4) . ?
C37 C40 1.529(4) . ?
C37 C39 1.532(4) . ?
C37 C38 1.537(4) . ?
C41 C43 1.528(4) . ?
C41 C44 1.532(4) . ?
C41 C42 1.535(4) . ?
C45 C46 1.377(5) . ?
C45 C50 1.378(5) . ?
C46 C47 1.376(5) . ?
C47 C48 1.364(5) . ?
C48 C49 1.365(5) . ?
C49 C50 1.377(6) . ?
C51 C56 1.377(4) . ?
C51 C52 1.383(5) . ?
C52 C53 1.378(5) . ?
C53 C54 1.375(5) . ?
C54 C55 1.389(5) . ?
C55 C56 1.379(5) . ?

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
O1 Ni1 N1 86.03(8) . . ?
O1 Ni1 N2 89.55(8) . . ?
N1 Ni1 N2 175.58(9) . . ?
O1 Ni1 N3 171.84(9) . . ?
N1 Ni1 N3 101.93(9) . . ?
N2 Ni1 N3 82.47(9) . . ?
C1 O1 Ni1 113.76(15) . . ?
C2 N1 C15 116.3(2) . . ?
C2 N1 Ni1 111.94(16) . . ?
C15 N1 Ni1 127.84(17) . . ?
C31 N2 C27 117.3(2) . . ?
C31 N2 Ni1 116.14(17) . . ?
C27 N2 Ni1 126.46(18) . . ?
C36 N3 C32 115.9(2) . . ?
C36 N3 Ni1 129.58(17) . . ?
C32 N3 Ni1 114.23(16) . . ?
O1 C1 C6 124.6(2) . . ?
O1 C1 C2 114.5(2) . . ?
C6 C1 C2 120.9(2) . . ?
N1 C2 C3 126.5(2) . . ?
N1 C2 C1 113.6(2) . . ?
C3 C2 C1 119.9(2) . . ?
C4 C3 C2 120.4(2) . . ?
C3 C4 C5 118.5(2) . . ?
C3 C4 C7 118.7(2) . . ?
C5 C4 C7 122.8(2) . . ?
C4 C5 C6 122.8(2) . . ?
C1 C6 C5 117.2(2) . . ?
C1 C6 C11 121.3(2) . . ?
C5 C6 C11 121.5(2) . . ?
C8 C7 C10 107.6(2) . . ?
C8 C7 C9 109.2(2) . . ?
C10 C7 C9 108.0(2) . . ?
C8 C7 C4 109.1(2) . . ?
C10 C7 C4 113.0(2) . . ?
C9 C7 C4 109.9(2) . . ?
C6 C11 C13 112.8(2) . . ?
C6 C11 C14 110.5(2) . . ?
C13 C11 C14 107.8(2) . . ?
C6 C11 C12 109.1(2) . . ?
C13 C11 C12 107.2(2) . . ?
C14 C11 C12 109.2(2) . . ?
C20 C15 C16 120.5(2) . . ?
C20 C15 N1 119.9(2) . . ?
C16 C15 N1 119.6(2) . . ?
C17 C16 C15 118.1(3) . . ?
C17 C16 C21 122.0(2) . . ?
C15 C16 C21 120.0(2) . . ?
C18 C17 C16 121.4(3) . . ?
C17 C18 C19 120.1(3) . . ?
C18 C19 C20 120.6(3) . . ?
C19 C20 C15 119.1(3) . . ?
C19 C20 C24 119.5(3) . . ?
C15 C20 C24 121.4(2) . . ?
C16 C21 C23 113.3(3) . . ?
C16 C21 C22 112.2(2) . . ?
C23 C21 C22 110.0(3) . . ?
C25 C24 C26 111.4(3) . . ?
C25 C24 C20 112.6(3) . . ?
C26 C24 C20 110.6(3) . . ?
N2 C27 C28 122.6(3) . . ?
C27 C28 C29 120.5(3) . . ?
C30 C29 C28 116.6(2) . . ?
C30 C29 C37 122.7(2) . . ?
C28 C29 C37 120.6(2) . . ?
C29 C30 C31 120.2(3) . . ?
N2 C31 C30 122.7(2) . . ?
N2 C31 C32 113.1(2) . . ?
C30 C31 C32 124.1(2) . . ?
N3 C32 C33 122.9(2) . . ?
N3 C32 C31 113.7(2) . . ?
C33 C32 C31 123.4(2) . . ?
C32 C33 C34 121.4(2) . . ?
C33 C34 C35 115.3(2) . . ?
C33 C34 C41 123.0(2) . . ?
C35 C34 C41 121.6(2) . . ?
C36 C35 C34 121.0(2) . . ?
N3 C36 C35 123.5(2) . . ?
C40 C37 C39 108.8(3) . . ?
C40 C37 C29 112.3(2) . . ?
C39 C37 C29 107.8(2) . . ?
C40 C37 C38 109.2(3) . . ?
C39 C37 C38 109.4(3) . . ?
C29 C37 C38 109.3(2) . . ?
C34 C41 C43 107.5(2) . . ?
C34 C41 C44 112.0(2) . . ?
C43 C41 C44 109.7(2) . . ?
C34 C41 C42 109.4(2) . . ?
C43 C41 C42 110.1(3) . . ?
C44 C41 C42 108.3(3) . . ?
C46 C45 C50 119.6(3) . . ?
C47 C46 C45 119.8(3) . . ?
C48 C47 C46 120.4(4) . . ?
C47 C48 C49 119.9(4) . . ?
C48 C49 C50 120.4(3) . . ?
C49 C50 C45 119.7(4) . . ?
C56 C51 C52 119.5(3) . . ?
C53 C52 C51 120.5(3) . . ?
C54 C53 C52 119.7(3) . . ?
C53 C54 C55 120.1(3) . . ?
C56 C55 C54 119.8(3) . . ?
C51 C56 C55 120.3(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
N1 Ni1 O1 C1 3.95(16) . . . . ?
N2 Ni1 O1 C1 -175.77(16) . . . . ?
O1 Ni1 N1 C2 -2.25(17) . . . . ?
N3 Ni1 N1 C2 175.96(17) . . . . ?
O1 Ni1 N1 C15 154.4(2) . . . . ?
N3 Ni1 N1 C15 -27.4(2) . . . . ?
Ni1 O1 C1 C6 176.6(2) . . . . ?
Ni1 O1 C1 C2 -4.8(3) . . . . ?
C15 N1 C2 C3 22.6(4) . . . . ?
Ni1 N1 C2 C3 -177.8(2) . . . . ?
C15 N1 C2 C1 -159.4(2) . . . . ?
Ni1 N1 C2 C1 0.2(3) . . . . ?
O1 C1 C2 N1 3.0(3) . . . . ?
C6 C1 C2 N1 -178.3(2) . . . . ?
O1 C1 C2 C3 -178.9(2) . . . . ?
C6 C1 C2 C3 -0.2(4) . . . . ?
N1 C2 C3 C4 173.2(2) . . . . ?
C1 C2 C3 C4 -4.7(4) . . . . ?
C2 C3 C4 C5 5.6(4) . . . . ?
C2 C3 C4 C7 -172.0(2) . . . . ?
C3 C4 C5 C6 -1.7(4) . . . . ?
C7 C4 C5 C6 175.7(2) . . . . ?
O1 C1 C6 C5 -177.6(2) . . . . ?
C2 C1 C6 C5 3.9(4) . . . . ?
O1 C1 C6 C11 3.4(4) . . . . ?
C2 C1 C6 C11 -175.2(2) . . . . ?
C4 C5 C6 C1 -3.0(4) . . . . ?
C4 C5 C6 C11 176.1(2) . . . . ?
C3 C4 C7 C8 61.3(3) . . . . ?
C5 C4 C7 C8 -116.2(3) . . . . ?
C3 C4 C7 C10 -179.1(2) . . . . ?
C5 C4 C7 C10 3.5(3) . . . . ?
C3 C4 C7 C9 -58.4(3) . . . . ?
C5 C4 C7 C9 124.1(3) . . . . ?
C1 C6 C11 C13 177.3(2) . . . . ?
C5 C6 C11 C13 -1.7(3) . . . . ?
C1 C6 C11 C14 -61.9(3) . . . . ?
C5 C6 C11 C14 119.1(3) . . . . ?
C1 C6 C11 C12 58.2(3) . . . . ?
C5 C6 C11 C12 -120.8(3) . . . . ?
C2 N1 C15 C20 93.0(3) . . . . ?
Ni1 N1 C15 C20 -62.8(3) . . . . ?
C2 N1 C15 C16 -88.4(3) . . . . ?
Ni1 N1 C15 C16 115.8(2) . . . . ?
C20 C15 C16 C17 3.3(4) . . . . ?
N1 C15 C16 C17 -175.4(2) . . . . ?
C20 C15 C16 C21 -177.5(2) . . . . ?
N1 C15 C16 C21 3.9(4) . . . . ?
C15 C16 C17 C18 0.8(4) . . . . ?
C21 C16 C17 C18 -178.4(3) . . . . ?
C16 C17 C18 C19 -3.2(5) . . . . ?
C17 C18 C19 C20 1.6(5) . . . . ?
C18 C19 C20 C15 2.5(4) . . . . ?
C18 C19 C20 C24 -177.2(3) . . . . ?
C16 C15 C20 C19 -4.9(4) . . . . ?
N1 C15 C20 C19 173.7(2) . . . . ?
C16 C15 C20 C24 174.8(3) . . . . ?
N1 C15 C20 C24 -6.6(4) . . . . ?
C17 C16 C21 C23 -29.1(4) . . . . ?
C15 C16 C21 C23 151.6(3) . . . . ?
C17 C16 C21 C22 96.1(3) . . . . ?
C15 C16 C21 C22 -83.1(3) . . . . ?
C19 C20 C24 C25 -60.5(4) . . . . ?
C15 C20 C24 C25 119.8(3) . . . . ?
C19 C20 C24 C26 64.9(4) . . . . ?
C15 C20 C24 C26 -114.8(3) . . . . ?
C31 N2 C27 C28 1.1(4) . . . . ?
Ni1 N2 C27 C28 -175.2(2) . . . . ?
N2 C27 C28 C29 0.6(4) . . . . ?
C27 C28 C29 C30 -1.6(4) . . . . ?
C27 C28 C29 C37 176.1(2) . . . . ?
C28 C29 C30 C31 0.9(4) . . . . ?
C37 C29 C30 C31 -176.7(2) . . . . ?
C27 N2 C31 C30 -1.8(4) . . . . ?
Ni1 N2 C31 C30 174.82(19) . . . . ?
C27 N2 C31 C32 178.2(2) . . . . ?
Ni1 N2 C31 C32 -5.1(3) . . . . ?
C29 C30 C31 N2 0.9(4) . . . . ?
C29 C30 C31 C32 -179.2(2) . . . . ?
C36 N3 C32 C33 0.0(4) . . . . ?
Ni1 N3 C32 C33 174.11(19) . . . . ?
C36 N3 C32 C31 -178.1(2) . . . . ?
Ni1 N3 C32 C31 -3.9(3) . . . . ?
N2 C31 C32 N3 5.8(3) . . . . ?
C30 C31 C32 N3 -174.1(2) . . . . ?
N2 C31 C32 C33 -172.2(2) . . . . ?
C30 C31 C32 C33 7.9(4) . . . . ?
N3 C32 C33 C34 -0.2(4) . . . . ?
C31 C32 C33 C34 177.6(2) . . . . ?
C32 C33 C34 C35 -0.1(4) . . . . ?
C32 C33 C34 C41 -177.3(2) . . . . ?
C33 C34 C35 C36 0.7(4) . . . . ?
C41 C34 C35 C36 177.9(3) . . . . ?
C32 N3 C36 C35 0.6(4) . . . . ?
Ni1 N3 C36 C35 -172.4(2) . . . . ?
C34 C35 C36 N3 -1.0(4) . . . . ?
C30 C29 C37 C40 -2.0(4) . . . . ?
C28 C29 C37 C40 -179.5(3) . . . . ?
C30 C29 C37 C39 117.8(3) . . . . ?
C28 C29 C37 C39 -59.7(3) . . . . ?
C30 C29 C37 C38 -123.4(3) . . . . ?
C28 C29 C37 C38 59.2(3) . . . . ?
C33 C34 C41 C43 105.3(3) . . . . ?
C35 C34 C41 C43 -71.7(3) . . . . ?
C33 C34 C41 C44 -15.2(4) . . . . ?
C35 C34 C41 C44 167.8(3) . . . . ?
C33 C34 C41 C42 -135.2(3) . . . . ?
C35 C34 C41 C42 47.8(4) . . . . ?
C50 C45 C46 C47 -0.2(6) . . . . ?
C45 C46 C47 C48 -0.3(5) . . . . ?
C46 C47 C48 C49 -0.1(5) . . . . ?
C47 C48 C49 C50 1.1(5) . . . . ?
C48 C49 C50 C45 -1.6(5) . . . . ?
C46 C45 C50 C49 1.1(6) . . . . ?
C56 C51 C52 C53 -0.6(5) . . . . ?
C51 C52 C53 C54 1.3(5) . . . . ?
C52 C53 C54 C55 -1.4(5) . . . . ?
C53 C54 C55 C56 0.8(5) . . . . ?
C52 C51 C56 C55 -0.1(5) . . . . ?
C54 C55 C56 C51 0.0(5) . . . . ?

_refine_diff_density_max         0.449
_refine_diff_density_min         -0.255
_refine_diff_density_rms         0.050

_shelxl_version_number           2014-2

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_afh413
_database_code_depnum_ccdc_archive 'CCDC 1414824'
_audit_update_record             
;
2015-07-23 deposited with the CCDC.
2015-11-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C54 H65 N3 Ni O2'
_chemical_formula_weight         846.80

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   10.3735(5)
_cell_length_b                   18.2520(8)
_cell_length_c                   24.6774(11)
_cell_angle_alpha                90
_cell_angle_beta                 97.1921(6)
_cell_angle_gamma                90
_cell_volume                     4635.6(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    88(2)
_cell_measurement_reflns_used    9788
_cell_measurement_theta_min      2.27
_cell_measurement_theta_max      28.75

_exptl_crystal_description       irregular
_exptl_crystal_colour            black
_exptl_crystal_density_meas      not_measured
_exptl_crystal_density_method    not_measured
_exptl_crystal_density_diffrn    1.213
_exptl_crystal_F_000             1816
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.420
_exptl_crystal_size_mid          0.378
_exptl_crystal_size_min          0.353
_exptl_absorpt_coefficient_mu    0.462
_shelx_estimated_absorpt_T_min   0.830
_shelx_estimated_absorpt_T_max   0.854
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.8719
_exptl_absorpt_correction_T_max  0.9228
_exptl_absorpt_process_details   'Bruker SADABS 2012/1'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      88(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker SMART APEX II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            55375
_diffrn_reflns_av_unetI/netI     0.0169
_diffrn_reflns_av_R_equivalents  0.0203
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_theta_min         1.392
_diffrn_reflns_theta_max         29.054
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.946
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.946
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.946
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             11708
_reflns_number_gt                10277
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'Bruker APEX2 2013.10-0, 2013'
_computing_cell_refinement       'Bruker SAINT 8.34a, 2013'
_computing_data_reduction        'Bruker SAINT 8.34a, 2013'
_computing_structure_solution    'Bruker SHELXTL 2013/1'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 ? 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0358P)²+2.7200P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         11708
_refine_ls_number_parameters     801
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0384
_refine_ls_R_factor_gt           0.0312
_refine_ls_wR_factor_ref         0.0795
_refine_ls_wR_factor_gt          0.0753
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_restrained_S_all      1.022
_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_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 0.32416(2) 0.20413(2) 0.30446(2) 0.01111(4) Uani 1 1 d . . . . .
O1 O 0.26192(8) 0.26441(5) 0.35395(3) 0.01438(16) Uani 1 1 d . . . . .
N1 N 0.15170(9) 0.20082(5) 0.27040(4) 0.01287(19) Uani 1 1 d . . . . .
N2 N 0.48251(10) 0.19574(5) 0.35226(4) 0.01325(19) Uani 1 1 d . . . . .
N3 N 0.41703(9) 0.14488(5) 0.25712(4) 0.01300(19) Uani 1 1 d . . . . .
C1 C 0.13344(11) 0.27560(6) 0.34410(5) 0.0126(2) Uani 1 1 d . . . . .
C2 C 0.06826(11) 0.24275(6) 0.29789(5) 0.0122(2) Uani 1 1 d . . . . .
C3 C -0.07154(11) 0.25248(6) 0.28616(5) 0.0129(2) Uani 1 1 d . . . . .
C4 C -0.15002(12) 0.21675(7) 0.24249(5) 0.0163(2) Uani 1 1 d . . . . .
C5 C -0.28137(12) 0.22955(7) 0.23121(5) 0.0181(2) Uani 1 1 d . . . . .
C6 C -0.34318(12) 0.27818(7) 0.26356(5) 0.0185(2) Uani 1 1 d . . . . .
C7 C -0.27161(12) 0.31096(7) 0.30772(5) 0.0176(2) Uani 1 1 d . . . . .
C8 C -0.13655(12) 0.29954(6) 0.32077(5) 0.0142(2) Uani 1 1 d . . . . .
C9 C -0.06503(12) 0.33397(6) 0.36835(5) 0.0144(2) Uani 1 1 d . . . . .
C10 C -0.12272(13) 0.38027(7) 0.40465(5) 0.0181(2) Uani 1 1 d . . . . .
C11 C -0.05172(14) 0.41005(7) 0.45037(5) 0.0207(3) Uani 1 1 d . . . . .
C12 C 0.08132(13) 0.39425(7) 0.46247(5) 0.0198(2) Uani 1 1 d . . . . .
C13 C 0.14131(12) 0.35004(7) 0.42808(5) 0.0167(2) Uani 1 1 d . . . . .
C14 C 0.07032(12) 0.31970(6) 0.38034(5) 0.0135(2) Uani 1 1 d . . . . .
C15 C 0.11268(11) 0.16877(6) 0.21860(5) 0.0127(2) Uani 1 1 d . . . . .
C16 C 0.09455(11) 0.21197(6) 0.17088(5) 0.0140(2) Uani 1 1 d . . . . .
C17 C 0.06319(12) 0.17725(7) 0.12037(5) 0.0170(2) Uani 1 1 d . . . . .
C18 C 0.05141(12) 0.10154(7) 0.11697(5) 0.0189(2) Uani 1 1 d . . . . .
C19 C 0.07202(12) 0.05908(7) 0.16400(5) 0.0180(2) Uani 1 1 d . . . . .
C20 C 0.10271(11) 0.09130(6) 0.21526(5) 0.0147(2) Uani 1 1 d . . . . .
C21 C 0.11304(13) 0.29479(7) 0.17303(5) 0.0176(2) Uani 1 1 d . . . . .
C22 C 0.23314(16) 0.31664(8) 0.14659(7) 0.0301(3) Uani 1 1 d . . . . .
C23 C -0.00775(16) 0.33511(8) 0.14610(6) 0.0289(3) Uani 1 1 d . . . . .
C24 C 0.12968(13) 0.04521(7) 0.26678(5) 0.0177(2) Uani 1 1 d . . . . .
C25 C 0.16869(18) -0.03361(8) 0.25571(7) 0.0311(3) Uani 1 1 d . . . . .
C26 C 0.01562(14) 0.04641(8) 0.30066(6) 0.0231(3) Uani 1 1 d . . . . .
C27 C 0.51225(12) 0.23039(7) 0.40047(5) 0.0158(2) Uani 1 1 d . . . . .
C28 C 0.62198(12) 0.21375(7) 0.43585(5) 0.0176(2) Uani 1 1 d . . . . .
C29 C 0.70743(12) 0.15864(7) 0.42293(5) 0.0156(2) Uani 1 1 d . . . . .
C30 C 0.67803(12) 0.12494(7) 0.37233(5) 0.0153(2) Uani 1 1 d . . . . .
C31 C 0.56575(11) 0.14428(6) 0.33828(5) 0.0133(2) Uani 1 1 d . . . . .
C32 C 0.52642(11) 0.11329(6) 0.28377(5) 0.0131(2) Uani 1 1 d . . . . .
C33 C 0.59488(11) 0.05942(6) 0.26023(5) 0.0144(2) Uani 1 1 d . . . . .
C34 C 0.55739(11) 0.03644(6) 0.20656(5) 0.0139(2) Uani 1 1 d . . . . .
C35 C 0.45403(12) 0.07464(7) 0.17805(5) 0.0159(2) Uani 1 1 d . . . . .
C36 C 0.38740(11) 0.12730(7) 0.20401(5) 0.0150(2) Uani 1 1 d . . . . .
C37 C 0.82266(12) 0.13604(7) 0.46421(5) 0.0177(2) Uani 1 1 d . . . . .
C38 C 0.90600(16) 0.07708(10) 0.44153(6) 0.0324(4) Uani 1 1 d . . . . .
C39 C 0.76906(14) 0.10497(8) 0.51480(6) 0.0235(3) Uani 1 1 d . . . . .
C40 C 0.90808(14) 0.20322(8) 0.48073(6) 0.0252(3) Uani 1 1 d . . . . .
C41 C 0.63016(12) -0.02472(6) 0.18144(5) 0.0157(2) Uani 1 1 d . . . . .
C42 C 0.55159(14) -0.05564(8) 0.12973(6) 0.0242(3) Uani 1 1 d . . . . .
C43 C 0.65951(18) -0.08701(8) 0.22287(6) 0.0305(3) Uani 1 1 d . . . . .
C44 C 0.75829(13) 0.00660(8) 0.16611(6) 0.0236(3) Uani 1 1 d . . . . .
O2 O 1.38723(10) 0.04894(6) 0.43512(5) 0.0333(2) Uani 1 1 d . . . . .
C45 C 1.2770(2) 0.14404(12) 0.47864(9) 0.0442(4) Uani 1 1 d . . . . .
C46 C 1.27253(15) 0.09339(9) 0.43044(7) 0.0309(3) Uani 1 1 d . . . . .
C47 C 1.38494(16) -0.00087(9) 0.39081(7) 0.0351(4) Uani 1 1 d . . . . .
C48 C 1.5041(2) -0.04934(12) 0.40041(13) 0.0585(6) Uani 1 1 d . . . . .
C49 C 0.43682(16) 0.32129(9) 0.54767(7) 0.0330(3) Uani 1 1 d . . . . .
C50 C 0.47165(16) 0.37861(9) 0.51575(6) 0.0311(3) Uani 1 1 d . . . . .
C51 C 0.60144(17) 0.39652(9) 0.51566(6) 0.0323(3) Uani 1 1 d . . . . .
C52 C 0.69656(16) 0.35735(9) 0.54787(6) 0.0325(3) Uani 1 1 d . . . . .
C53 C 0.66230(17) 0.30032(9) 0.58003(6) 0.0332(3) Uani 1 1 d . . . . .
C54 C 0.53242(18) 0.28199(9) 0.57991(6) 0.0346(4) Uani 1 1 d . . . . .
H4A H -0.1122(16) 0.1839(9) 0.2192(7) 0.022(4) Uiso 1 1 d . . . . .
H5A H -0.3316(16) 0.2040(9) 0.2015(7) 0.022(4) Uiso 1 1 d . . . . .
H6A H -0.4343(16) 0.2871(9) 0.2559(7) 0.023(4) Uiso 1 1 d . . . . .
H7A H -0.3136(16) 0.3414(9) 0.3308(7) 0.023(4) Uiso 1 1 d . . . . .
H10A H -0.2141(16) 0.3910(9) 0.3973(6) 0.020(4) Uiso 1 1 d . . . . .
H11A H -0.0924(16) 0.4402(9) 0.4741(7) 0.024(4) Uiso 1 1 d . . . . .
H12A H 0.1300(16) 0.4140(9) 0.4946(7) 0.025(4) Uiso 1 1 d . . . . .
H13A H 0.2323(16) 0.3400(8) 0.4359(6) 0.019(4) Uiso 1 1 d . . . . .
H17A H 0.0502(14) 0.2054(8) 0.0883(6) 0.012(3) Uiso 1 1 d . . . . .
H18A H 0.0300(15) 0.0788(9) 0.0829(7) 0.022(4) Uiso 1 1 d . . . . .
H19A H 0.0644(15) 0.0062(9) 0.1607(7) 0.022(4) Uiso 1 1 d . . . . .
H21A H 0.1271(15) 0.3101(8) 0.2106(6) 0.016(4) Uiso 1 1 d . . . . .
H22A H 0.312(2) 0.2942(11) 0.1662(8) 0.043(5) Uiso 1 1 d . . . . .
H22B H 0.2453(19) 0.3698(12) 0.1478(8) 0.046(6) Uiso 1 1 d . . . . .
H22C H 0.2259(19) 0.3012(10) 0.1078(8) 0.038(5) Uiso 1 1 d . . . . .
H23A H -0.0849(19) 0.3234(11) 0.1651(8) 0.040(5) Uiso 1 1 d . . . . .
H23B H -0.0240(19) 0.3224(11) 0.1074(8) 0.041(5) Uiso 1 1 d . . . . .
H23C H 0.0083(18) 0.3871(11) 0.1478(8) 0.036(5) Uiso 1 1 d . . . . .
H24A H 0.2013(15) 0.0685(8) 0.2888(6) 0.017(4) Uiso 1 1 d . . . . .
H25A H 0.2425(19) -0.0349(11) 0.2337(8) 0.040(5) Uiso 1 1 d . . . . .
H25B H 0.098(2) -0.0614(11) 0.2368(8) 0.043(5) Uiso 1 1 d . . . . .
H25C H 0.1961(18) -0.0594(10) 0.2905(8) 0.036(5) Uiso 1 1 d . . . . .
H26A H -0.0108(17) 0.0967(11) 0.3080(7) 0.034(5) Uiso 1 1 d . . . . .
H26B H 0.0389(17) 0.0216(10) 0.3354(7) 0.028(4) Uiso 1 1 d . . . . .
H26C H -0.0574(18) 0.0233(10) 0.2827(7) 0.034(5) Uiso 1 1 d . . . . .
H27A H 0.4502(15) 0.2654(9) 0.4085(6) 0.018(4) Uiso 1 1 d . . . . .
H28A H 0.6367(15) 0.2395(9) 0.4690(7) 0.021(4) Uiso 1 1 d . . . . .
H30A H 0.7347(15) 0.0889(9) 0.3600(6) 0.017(4) Uiso 1 1 d . . . . .
H33A H 0.6689(17) 0.0380(9) 0.2818(7) 0.026(4) Uiso 1 1 d . . . . .
H35A H 0.4273(15) 0.0661(9) 0.1405(7) 0.020(4) Uiso 1 1 d . . . . .
H36A H 0.3181(15) 0.1519(8) 0.1850(6) 0.017(4) Uiso 1 1 d . . . . .
H38A H 0.8593(19) 0.0319(11) 0.4332(8) 0.039(5) Uiso 1 1 d . . . . .
H38B H 0.9783(18) 0.0644(10) 0.4698(7) 0.034(5) Uiso 1 1 d . . . . .
H38C H 0.9438(18) 0.0958(11) 0.4097(8) 0.037(5) Uiso 1 1 d . . . . .
H39A H 0.7105(19) 0.0612(11) 0.5057(8) 0.043(5) Uiso 1 1 d . . . . .
H39B H 0.7205(18) 0.1424(10) 0.5327(7) 0.033(5) Uiso 1 1 d . . . . .
H39C H 0.8426(17) 0.0884(9) 0.5416(7) 0.027(4) Uiso 1 1 d . . . . .
H40A H 0.9433(18) 0.2215(10) 0.4511(8) 0.033(5) Uiso 1 1 d . . . . .
H40B H 0.9833(18) 0.1886(10) 0.5075(7) 0.030(4) Uiso 1 1 d . . . . .
H40C H 0.8590(18) 0.2430(11) 0.4975(8) 0.036(5) Uiso 1 1 d . . . . .
H42A H 0.4655(19) -0.0713(10) 0.1372(8) 0.037(5) Uiso 1 1 d . . . . .
H42B H 0.5988(17) -0.0967(10) 0.1167(7) 0.028(4) Uiso 1 1 d . . . . .
H42C H 0.5390(17) -0.0197(10) 0.1008(8) 0.032(5) Uiso 1 1 d . . . . .
H43A H 0.5779(19) -0.1034(10) 0.2356(8) 0.038(5) Uiso 1 1 d . . . . .
H43B H 0.7209(19) -0.0723(11) 0.2550(8) 0.043(5) Uiso 1 1 d . . . . .
H43C H 0.7009(17) -0.1262(10) 0.2053(7) 0.033(5) Uiso 1 1 d . . . . .
H44A H 0.7408(18) 0.0469(11) 0.1385(8) 0.036(5) Uiso 1 1 d . . . . .
H44B H 0.8062(16) -0.0328(10) 0.1516(7) 0.027(4) Uiso 1 1 d . . . . .
H44C H 0.8092(18) 0.0292(10) 0.1977(8) 0.035(5) Uiso 1 1 d . . . . .
H45A H 1.197(2) 0.1805(14) 0.4734(10) 0.067(7) Uiso 1 1 d . . . . .
H45B H 1.363(2) 0.1704(13) 0.4840(9) 0.058(6) Uiso 1 1 d . . . . .
H45C H 1.281(2) 0.1125(13) 0.5110(10) 0.058(7) Uiso 1 1 d . . . . .
H46A H 1.1936(17) 0.0618(10) 0.4297(7) 0.030(4) Uiso 1 1 d . . . . .
H46B H 1.2623(17) 0.1217(10) 0.3968(7) 0.031(4) Uiso 1 1 d . . . . .
H47A H 1.3807(18) 0.0259(10) 0.3549(8) 0.036(5) Uiso 1 1 d . . . . .
H47B H 1.3024(18) -0.0309(10) 0.3883(7) 0.031(5) Uiso 1 1 d . . . . .
H48A H 1.494(2) -0.0807(13) 0.3680(9) 0.049(6) Uiso 1 1 d . . . . .
H48B H 1.505(3) -0.0791(15) 0.4344(11) 0.077(8) Uiso 1 1 d . . . . .
H48C H 1.585(2) -0.0195(13) 0.3991(9) 0.064(7) Uiso 1 1 d . . . . .
H49A H 0.345(2) 0.3091(11) 0.5482(8) 0.043(5) Uiso 1 1 d . . . . .
H50A H 0.4068(19) 0.4058(11) 0.4951(8) 0.041(5) Uiso 1 1 d . . . . .
H51A H 0.6254(18) 0.4342(11) 0.4929(8) 0.038(5) Uiso 1 1 d . . . . .
H52A H 0.784(2) 0.3707(11) 0.5477(8) 0.039(5) Uiso 1 1 d . . . . .
H53A H 0.7227(19) 0.2727(11) 0.6019(8) 0.040(5) Uiso 1 1 d . . . . .
H54A H 0.511(2) 0.2440(12) 0.6016(9) 0.050(6) Uiso 1 1 d . . . . .


_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 O1 1.8212(8) . ?
Ni1 N1 1.8798(10) . ?
Ni1 N2 1.9048(10) . ?
Ni1 N3 1.9350(10) . ?
O1 C1 1.3401(14) . ?
N1 C2 1.3936(14) . ?
N1 C15 1.4178(14) . ?
N2 C27 1.3485(15) . ?
N2 C31 1.3496(15) . ?
N3 C36 1.3469(15) . ?
N3 C32 1.3659(15) . ?
C1 C2 1.3871(16) . ?
C1 C14 1.4224(16) . ?
C2 C3 1.4537(16) . ?
C3 C4 1.4247(16) . ?
C3 C8 1.4374(16) . ?
C4 C5 1.3761(17) . ?
C5 C6 1.4016(18) . ?
C6 C7 1.3764(19) . ?
C7 C8 1.4132(17) . ?
C8 C9 1.4512(17) . ?
C9 C10 1.4174(16) . ?
C9 C14 1.4222(17) . ?
C10 C11 1.3793(19) . ?
C11 C12 1.4049(19) . ?
C12 C13 1.3750(17) . ?
C13 C14 1.4211(17) . ?
C15 C16 1.4102(16) . ?
C15 C20 1.4194(16) . ?
C16 C17 1.3997(16) . ?
C16 C21 1.5239(16) . ?
C17 C18 1.3888(18) . ?
C18 C19 1.3897(19) . ?
C19 C20 1.3953(17) . ?
C20 C24 1.5210(17) . ?
C21 C22 1.5298(19) . ?
C21 C23 1.5313(19) . ?
C24 C25 1.5284(18) . ?
C24 C26 1.5320(18) . ?
C27 C28 1.3789(17) . ?
C28 C29 1.4034(17) . ?
C29 C30 1.3911(17) . ?
C29 C37 1.5271(16) . ?
C30 C31 1.3935(16) . ?
C31 C32 1.4692(16) . ?
C32 C33 1.3826(16) . ?
C33 C34 1.3974(16) . ?
C34 C35 1.3935(17) . ?
C34 C41 1.5224(16) . ?
C35 C36 1.3867(17) . ?
C37 C38 1.5296(19) . ?
C37 C39 1.5371(18) . ?
C37 C40 1.5376(19) . ?
C41 C42 1.5330(18) . ?
C41 C43 1.5339(18) . ?
C41 C44 1.5370(18) . ?
O2 C47 1.420(2) . ?
O2 C46 1.4329(18) . ?
C45 C46 1.503(3) . ?
C47 C48 1.515(3) . ?
C49 C50 1.385(2) . ?
C49 C54 1.390(2) . ?
C50 C51 1.386(2) . ?
C51 C52 1.386(2) . ?
C52 C53 1.382(2) . ?
C53 C54 1.388(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
O1 Ni1 N1 85.52(4) . . ?
O1 Ni1 N2 89.07(4) . . ?
N1 Ni1 N2 166.63(4) . . ?
O1 Ni1 N3 170.99(4) . . ?
N1 Ni1 N3 103.30(4) . . ?
N2 Ni1 N3 82.70(4) . . ?
C1 O1 Ni1 113.48(7) . . ?
C2 N1 C15 122.73(10) . . ?
C2 N1 Ni1 112.28(8) . . ?
C15 N1 Ni1 124.37(8) . . ?
C27 N2 C31 117.96(10) . . ?
C27 N2 Ni1 126.36(8) . . ?
C31 N2 Ni1 115.31(8) . . ?
C36 N3 C32 116.27(10) . . ?
C36 N3 Ni1 130.57(8) . . ?
C32 N3 Ni1 113.06(8) . . ?
O1 C1 C2 117.04(10) . . ?
O1 C1 C14 119.86(10) . . ?
C2 C1 C14 123.10(11) . . ?
C1 C2 N1 111.65(10) . . ?
C1 C2 C3 118.84(10) . . ?
N1 C2 C3 129.42(10) . . ?
C4 C3 C8 117.18(11) . . ?
C4 C3 C2 123.79(11) . . ?
C8 C3 C2 119.02(10) . . ?
C5 C4 C3 122.20(11) . . ?
C4 C5 C6 120.28(12) . . ?
C7 C6 C5 119.11(11) . . ?
C6 C7 C8 122.50(12) . . ?
C7 C8 C3 118.58(11) . . ?
C7 C8 C9 120.81(11) . . ?
C3 C8 C9 120.61(11) . . ?
C10 C9 C14 117.49(11) . . ?
C10 C9 C8 123.79(11) . . ?
C14 C9 C8 118.71(10) . . ?
C11 C10 C9 121.83(12) . . ?
C10 C11 C12 120.18(12) . . ?
C13 C12 C11 119.85(12) . . ?
C12 C13 C14 120.84(12) . . ?
C13 C14 C9 119.79(11) . . ?
C13 C14 C1 120.68(11) . . ?
C9 C14 C1 119.54(11) . . ?
C16 C15 N1 121.03(10) . . ?
C16 C15 C20 120.48(11) . . ?
N1 C15 C20 118.28(10) . . ?
C17 C16 C15 118.84(11) . . ?
C17 C16 C21 119.63(11) . . ?
C15 C16 C21 121.49(10) . . ?
C18 C17 C16 120.88(12) . . ?
C17 C18 C19 120.08(11) . . ?
C18 C19 C20 121.06(12) . . ?
C19 C20 C15 118.64(11) . . ?
C19 C20 C24 121.46(11) . . ?
C15 C20 C24 119.87(10) . . ?
C16 C21 C22 110.45(11) . . ?
C16 C21 C23 111.66(11) . . ?
C22 C21 C23 110.82(12) . . ?
C20 C24 C25 113.35(11) . . ?
C20 C24 C26 111.99(11) . . ?
C25 C24 C26 110.54(11) . . ?
N2 C27 C28 122.33(11) . . ?
C27 C28 C29 120.59(11) . . ?
C30 C29 C28 116.55(11) . . ?
C30 C29 C37 123.00(11) . . ?
C28 C29 C37 120.40(11) . . ?
C29 C30 C31 120.14(11) . . ?
N2 C31 C30 122.36(11) . . ?
N2 C31 C32 112.87(10) . . ?
C30 C31 C32 124.75(11) . . ?
N3 C32 C33 122.51(11) . . ?
N3 C32 C31 113.40(10) . . ?
C33 C32 C31 124.05(11) . . ?
C32 C33 C34 121.00(11) . . ?
C35 C34 C33 115.70(11) . . ?
C35 C34 C41 123.41(11) . . ?
C33 C34 C41 120.85(11) . . ?
C36 C35 C34 120.66(11) . . ?
N3 C36 C35 123.26(11) . . ?
C29 C37 C38 112.15(10) . . ?
C29 C37 C39 107.99(10) . . ?
C38 C37 C39 108.43(12) . . ?
C29 C37 C40 109.78(10) . . ?
C38 C37 C40 108.95(12) . . ?
C39 C37 C40 109.51(11) . . ?
C34 C41 C42 111.70(10) . . ?
C34 C41 C43 109.83(10) . . ?
C42 C41 C43 108.82(11) . . ?
C34 C41 C44 108.39(10) . . ?
C42 C41 C44 108.55(11) . . ?
C43 C41 C44 109.52(12) . . ?
C47 O2 C46 111.51(12) . . ?
O2 C46 C45 109.95(14) . . ?
O2 C47 C48 108.60(18) . . ?
C50 C49 C54 119.81(16) . . ?
C49 C50 C51 120.12(15) . . ?
C52 C51 C50 119.98(16) . . ?
C53 C52 C51 120.13(16) . . ?
C52 C53 C54 119.98(15) . . ?
C53 C54 C49 119.96(16) . . ?

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
N1 Ni1 O1 C1 1.19(8) . . . . ?
N2 Ni1 O1 C1 -166.57(8) . . . . ?
O1 Ni1 N1 C2 -0.13(8) . . . . ?
N2 Ni1 N1 C2 66.3(2) . . . . ?
N3 Ni1 N1 C2 -178.24(8) . . . . ?
O1 Ni1 N1 C15 171.05(10) . . . . ?
N2 Ni1 N1 C15 -122.52(18) . . . . ?
N3 Ni1 N1 C15 -7.05(10) . . . . ?
Ni1 O1 C1 C2 -2.09(13) . . . . ?
Ni1 O1 C1 C14 178.04(8) . . . . ?
O1 C1 C2 N1 1.95(15) . . . . ?
C14 C1 C2 N1 -178.18(10) . . . . ?
O1 C1 C2 C3 178.99(10) . . . . ?
C14 C1 C2 C3 -1.14(17) . . . . ?
C15 N1 C2 C1 -172.26(10) . . . . ?
Ni1 N1 C2 C1 -0.91(12) . . . . ?
C15 N1 C2 C3 11.09(18) . . . . ?
Ni1 N1 C2 C3 -177.56(10) . . . . ?
C1 C2 C3 C4 -174.82(11) . . . . ?
N1 C2 C3 C4 1.62(19) . . . . ?
C1 C2 C3 C8 3.93(16) . . . . ?
N1 C2 C3 C8 -179.63(11) . . . . ?
C8 C3 C4 C5 3.94(18) . . . . ?
C2 C3 C4 C5 -177.29(11) . . . . ?
C3 C4 C5 C6 -1.04(19) . . . . ?
C4 C5 C6 C7 -2.14(19) . . . . ?
C5 C6 C7 C8 2.30(19) . . . . ?
C6 C7 C8 C3 0.68(18) . . . . ?
C6 C7 C8 C9 -178.75(11) . . . . ?
C4 C3 C8 C7 -3.69(16) . . . . ?
C2 C3 C8 C7 177.48(10) . . . . ?
C4 C3 C8 C9 175.74(10) . . . . ?
C2 C3 C8 C9 -3.09(16) . . . . ?
C7 C8 C9 C10 0.17(18) . . . . ?
C3 C8 C9 C10 -179.25(11) . . . . ?
C7 C8 C9 C14 178.84(11) . . . . ?
C3 C8 C9 C14 -0.57(16) . . . . ?
C14 C9 C10 C11 -0.74(18) . . . . ?
C8 C9 C10 C11 177.95(12) . . . . ?
C9 C10 C11 C12 -0.68(19) . . . . ?
C10 C11 C12 C13 1.2(2) . . . . ?
C11 C12 C13 C14 -0.24(19) . . . . ?
C12 C13 C14 C9 -1.20(18) . . . . ?
C12 C13 C14 C1 178.30(11) . . . . ?
C10 C9 C14 C13 1.66(16) . . . . ?
C8 C9 C14 C13 -177.10(10) . . . . ?
C10 C9 C14 C1 -177.85(11) . . . . ?
C8 C9 C14 C1 3.39(16) . . . . ?
O1 C1 C14 C13 -2.23(17) . . . . ?
C2 C1 C14 C13 177.90(11) . . . . ?
O1 C1 C14 C9 177.27(10) . . . . ?
C2 C1 C14 C9 -2.60(17) . . . . ?
C2 N1 C15 C16 73.45(15) . . . . ?
Ni1 N1 C15 C16 -96.84(12) . . . . ?
C2 N1 C15 C20 -111.71(12) . . . . ?
Ni1 N1 C15 C20 78.00(13) . . . . ?
N1 C15 C16 C17 176.41(10) . . . . ?
C20 C15 C16 C17 1.68(17) . . . . ?
N1 C15 C16 C21 -1.40(17) . . . . ?
C20 C15 C16 C21 -176.13(11) . . . . ?
C15 C16 C17 C18 -0.72(18) . . . . ?
C21 C16 C17 C18 177.13(11) . . . . ?
C16 C17 C18 C19 -0.61(19) . . . . ?
C17 C18 C19 C20 1.00(19) . . . . ?
C18 C19 C20 C15 -0.04(18) . . . . ?
C18 C19 C20 C24 -178.02(11) . . . . ?
C16 C15 C20 C19 -1.31(17) . . . . ?
N1 C15 C20 C19 -176.18(10) . . . . ?
C16 C15 C20 C24 176.71(11) . . . . ?
N1 C15 C20 C24 1.83(16) . . . . ?
C17 C16 C21 C22 -66.59(15) . . . . ?
C15 C16 C21 C22 111.20(13) . . . . ?
C17 C16 C21 C23 57.20(15) . . . . ?
C15 C16 C21 C23 -125.01(13) . . . . ?
C19 C20 C24 C25 21.17(17) . . . . ?
C15 C20 C24 C25 -156.79(12) . . . . ?
C19 C20 C24 C26 -104.74(13) . . . . ?
C15 C20 C24 C26 77.30(14) . . . . ?
C31 N2 C27 C28 -1.54(18) . . . . ?
Ni1 N2 C27 C28 171.13(9) . . . . ?
N2 C27 C28 C29 -0.65(19) . . . . ?
C27 C28 C29 C30 2.66(18) . . . . ?
C27 C28 C29 C37 -174.93(12) . . . . ?
C28 C29 C30 C31 -2.53(18) . . . . ?
C37 C29 C30 C31 174.99(11) . . . . ?
C27 N2 C31 C30 1.66(17) . . . . ?
Ni1 N2 C31 C30 -171.82(9) . . . . ?
C27 N2 C31 C32 -176.95(10) . . . . ?
Ni1 N2 C31 C32 9.57(13) . . . . ?
C29 C30 C31 N2 0.42(18) . . . . ?
C29 C30 C31 C32 178.87(11) . . . . ?
C36 N3 C32 C33 -7.78(17) . . . . ?
Ni1 N3 C32 C33 168.85(9) . . . . ?
C36 N3 C32 C31 169.90(10) . . . . ?
Ni1 N3 C32 C31 -13.46(12) . . . . ?
N2 C31 C32 N3 2.78(14) . . . . ?
C30 C31 C32 N3 -175.80(11) . . . . ?
N2 C31 C32 C33 -179.58(11) . . . . ?
C30 C31 C32 C33 1.85(19) . . . . ?
N3 C32 C33 C34 2.43(18) . . . . ?
C31 C32 C33 C34 -175.01(11) . . . . ?
C32 C33 C34 C35 4.29(17) . . . . ?
C32 C33 C34 C41 -177.86(11) . . . . ?
C33 C34 C35 C36 -5.50(17) . . . . ?
C41 C34 C35 C36 176.71(11) . . . . ?
C32 N3 C36 C35 6.56(17) . . . . ?
Ni1 N3 C36 C35 -169.37(9) . . . . ?
C34 C35 C36 N3 0.08(19) . . . . ?
C30 C29 C37 C38 4.44(18) . . . . ?
C28 C29 C37 C38 -178.13(13) . . . . ?
C30 C29 C37 C39 -114.97(13) . . . . ?
C28 C29 C37 C39 62.46(15) . . . . ?
C30 C29 C37 C40 125.70(13) . . . . ?
C28 C29 C37 C40 -56.87(15) . . . . ?
C35 C34 C41 C42 -18.61(17) . . . . ?
C33 C34 C41 C42 163.71(11) . . . . ?
C35 C34 C41 C43 -139.44(13) . . . . ?
C33 C34 C41 C43 42.87(16) . . . . ?
C35 C34 C41 C44 100.94(14) . . . . ?
C33 C34 C41 C44 -76.74(14) . . . . ?
C47 O2 C46 C45 178.66(13) . . . . ?
C46 O2 C47 C48 -176.18(13) . . . . ?
C54 C49 C50 C51 0.4(2) . . . . ?
C49 C50 C51 C52 -0.5(2) . . . . ?
C50 C51 C52 C53 0.1(2) . . . . ?
C51 C52 C53 C54 0.3(2) . . . . ?
C52 C53 C54 C49 -0.4(2) . . . . ?
C50 C49 C54 C53 0.1(2) . . . . ?

_refine_diff_density_max         0.563
_refine_diff_density_min         -0.370
_refine_diff_density_rms         0.049

_shelxl_version_number           2014-2


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: benzene and ether '
