# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_v160430_a
_database_code_depnum_ccdc_archive 'CCDC 1511825'
_audit_update_record             
;
2016-10-27 deposited with the CCDC.
2016-12-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16.50 H11 N3 Ni0.50'
_chemical_formula_weight         280.64

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   10.7913(16)
_cell_length_b                   23.085(4)
_cell_length_c                   9.7956(12)
_cell_angle_alpha                90
_cell_angle_beta                 98.370(14)
_cell_angle_gamma                90
_cell_volume                     2414.3(6)
_cell_formula_units_Z            8
_cell_measurement_temperature    93(2)
_cell_measurement_reflns_used    2466
_cell_measurement_theta_min      2.7280
_cell_measurement_theta_max      30.8280

_exptl_crystal_description       needle
_exptl_crystal_colour            black
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.544
_exptl_crystal_F_000             1160
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.750
_exptl_crystal_size_mid          0.020
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    0.842
_shelx_estimated_absorpt_T_min   0.571
_shelx_estimated_absorpt_T_max   0.983
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.44832
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      93(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 QUEST'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_reflns_number            7689
_diffrn_reflns_av_unetI/netI     0.0511
_diffrn_reflns_av_R_equivalents  0.0746
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.102
_diffrn_reflns_theta_max         24.994
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 0.970
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 0.970
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 0.970
_reflns_number_total             2129
_reflns_number_gt                1647
_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       ?
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.1985P)²+2.1688P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2129
_refine_ls_number_parameters     187
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1041
_refine_ls_R_factor_gt           0.0902
_refine_ls_wR_factor_ref         0.2814
_refine_ls_wR_factor_gt          0.2609
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_restrained_S_all      1.070
_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
C1 C 0.5000 0.3349(3) 0.7500 0.0443(18) Uani 1 2 d S T P . .
C2 C 0.4195(5) 0.3642(2) 0.6449(5) 0.0457(13) Uani 1 1 d . . . . .
C3 C 0.3292(5) 0.3457(2) 0.5315(5) 0.0458(13) Uani 1 1 d . . . . .
H1 H 0.3066 0.3067 0.5094 0.055 Uiso 1 1 calc R U . . .
C4 C 0.2804(5) 0.3941(2) 0.4595(5) 0.0451(13) Uani 1 1 d . . . . .
H2 H 0.2198 0.3946 0.3787 0.054 Uiso 1 1 calc R U . . .
C5 C 0.3393(5) 0.4434(2) 0.5311(5) 0.0448(13) Uani 1 1 d . . . . .
C6 C 0.3393(5) 0.5074(3) 0.5301(5) 0.0463(13) Uani 1 1 d . . . . .
C7 C 0.2914(5) 0.5568(2) 0.4500(5) 0.0454(13) Uani 1 1 d . . . . .
H3 H 0.2362 0.5561 0.3651 0.054 Uiso 1 1 calc R U . . .
C8 C 0.3410(5) 0.6052(2) 0.5200(5) 0.0442(13) Uani 1 1 d . . . . .
H4 H 0.3250 0.6442 0.4915 0.053 Uiso 1 1 calc R U . . .
C9 C 0.4209(5) 0.5872(2) 0.6430(5) 0.0447(13) Uani 1 1 d . . . . .
C10 C 0.5000 0.6160(4) 0.7500 0.0459(18) Uani 1 2 d S T P . .
C11 C 0.5000 0.2711(3) 0.7500 0.0435(17) Uani 1 2 d S T P . .
C12 C 0.5133(5) 0.2393(2) 0.6312(5) 0.0462(13) Uani 1 1 d . . . . .
H5 H 0.5203 0.2594 0.5481 0.055 Uiso 1 1 calc R U . . .
C13 C 0.5166(5) 0.1803(2) 0.6316(5) 0.0450(13) Uani 1 1 d . . . . .
H6 H 0.5304 0.1606 0.5500 0.054 Uiso 1 1 calc R U . . .
C14 C 0.5000 0.1473(3) 0.7500 0.0406(16) Uani 1 2 d S T P . .
C15 C 0.5314(6) 0.0570(2) 0.6323(5) 0.0550(15) Uani 1 1 d . . . . .
H7 H 0.4687 0.0649 0.5516 0.082 Uiso 1 1 calc R U . . .
H8 H 0.5326 0.0154 0.6526 0.082 Uiso 1 1 calc R U . . .
H9 H 0.6142 0.0691 0.6131 0.082 Uiso 1 1 calc R U . . .
C16 C 0.5000 0.6803(4) 0.7500 0.0457(18) Uani 1 2 d S T P . .
C17 C 0.6126(5) 0.7111(2) 0.7689(5) 0.0452(13) Uani 1 1 d . . . . .
H10 H 0.6898 0.6907 0.7829 0.054 Uiso 1 1 calc R U . . .
C18 C 0.6130(5) 0.7706(2) 0.7676(5) 0.0460(13) Uani 1 1 d . . . . .
H11 H 0.6901 0.7911 0.7786 0.055 Uiso 1 1 calc R U . . .
C19 C 0.5000 0.8006(3) 0.7500 0.0455(18) Uani 1 2 d S T P . .
C20 C 0.5000 0.8631(4) 0.7500 0.0492(19) Uani 1 2 d S T P . .
N1 N 0.4191(4) 0.42341(17) 0.6392(4) 0.0426(11) Uani 1 1 d . . . . .
N2 N 0.4155(4) 0.52836(17) 0.6419(4) 0.0433(12) Uani 1 1 d . . . . .
N3 N 0.5000 0.0888(3) 0.7500 0.0466(15) Uani 1 2 d S T P . .
N4 N 0.5000 0.9124(3) 0.7500 0.0602(18) Uani 1 2 d S T P . .
Ni1 Ni 0.5000 0.47574(4) 0.7500 0.0451(5) Uani 1 2 d S T P . .


_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
C1 C2 1.419(7) . ?
C1 C2 1.419(7) 2_656 ?
C1 C11 1.471(11) . ?
C2 N1 1.368(7) . ?
C2 C3 1.431(8) . ?
C3 C4 1.385(8) . ?
C3 H1 0.9500 . ?
C4 C5 1.436(8) . ?
C4 H2 0.9500 . ?
C5 N1 1.345(7) . ?
C5 C6 1.477(9) . ?
C6 N2 1.359(7) . ?
C6 C7 1.437(8) . ?
C7 C8 1.379(8) . ?
C7 H3 0.9500 . ?
C8 C9 1.437(7) . ?
C8 H4 0.9500 . ?
C9 N2 1.360(6) . ?
C9 C10 1.417(7) . ?
C10 C9 1.417(7) 2_656 ?
C10 C16 1.485(11) . ?
C11 C12 1.401(6) 2_656 ?
C11 C12 1.401(6) . ?
C12 C13 1.362(7) . ?
C12 H5 0.9500 . ?
C13 C14 1.421(6) . ?
C13 H6 0.9500 . ?
C14 N3 1.349(10) . ?
C14 C13 1.421(6) 2_656 ?
C15 N3 1.448(6) . ?
C15 H7 0.9800 . ?
C15 H8 0.9800 . ?
C15 H9 0.9800 . ?
C16 C17 1.397(7) . ?
C16 C17 1.397(7) 2_656 ?
C17 C18 1.372(7) . ?
C17 H10 0.9500 . ?
C18 C19 1.391(7) . ?
C18 H11 0.9500 . ?
C19 C18 1.391(7) 2_656 ?
C19 C20 1.444(11) . ?
C20 N4 1.137(10) . ?
N1 Ni1 1.767(4) . ?
N2 Ni1 1.774(4) . ?
N3 C15 1.448(6) 2_656 ?
Ni1 N1 1.767(4) 2_656 ?
Ni1 N2 1.774(5) 2_656 ?

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
C2 C1 C2 123.0(7) . 2_656 ?
C2 C1 C11 118.5(4) . . ?
C2 C1 C11 118.5(4) 2_656 . ?
N1 C2 C1 120.2(5) . . ?
N1 C2 C3 105.6(5) . . ?
C1 C2 C3 134.1(5) . . ?
C4 C3 C2 108.7(5) . . ?
C4 C3 H1 125.7 . . ?
C2 C3 H1 125.7 . . ?
C3 C4 C5 106.3(5) . . ?
C3 C4 H2 126.8 . . ?
C5 C4 H2 126.8 . . ?
N1 C5 C4 107.5(5) . . ?
N1 C5 C6 110.3(4) . . ?
C4 C5 C6 142.1(5) . . ?
N2 C6 C7 106.5(5) . . ?
N2 C6 C5 110.6(5) . . ?
C7 C6 C5 142.8(5) . . ?
C8 C7 C6 106.8(5) . . ?
C8 C7 H3 126.6 . . ?
C6 C7 H3 126.6 . . ?
C7 C8 C9 108.9(5) . . ?
C7 C8 H4 125.5 . . ?
C9 C8 H4 125.5 . . ?
N2 C9 C10 119.6(5) . . ?
N2 C9 C8 105.2(5) . . ?
C10 C9 C8 135.1(5) . . ?
C9 C10 C9 124.1(8) . 2_656 ?
C9 C10 C16 117.9(4) . . ?
C9 C10 C16 117.9(4) 2_656 . ?
C12 C11 C12 116.7(7) 2_656 . ?
C12 C11 C1 121.7(3) 2_656 . ?
C12 C11 C1 121.7(3) . . ?
C13 C12 C11 121.9(5) . . ?
C13 C12 H5 119.0 . . ?
C11 C12 H5 119.0 . . ?
C12 C13 C14 122.1(5) . . ?
C12 C13 H6 118.9 . . ?
C14 C13 H6 118.9 . . ?
N3 C14 C13 122.5(3) . . ?
N3 C14 C13 122.5(3) . 2_656 ?
C13 C14 C13 115.1(7) . 2_656 ?
N3 C15 H7 109.5 . . ?
N3 C15 H8 109.5 . . ?
H7 C15 H8 109.5 . . ?
N3 C15 H9 109.5 . . ?
H7 C15 H9 109.5 . . ?
H8 C15 H9 109.5 . . ?
C17 C16 C17 118.7(7) . 2_656 ?
C17 C16 C10 120.6(4) . . ?
C17 C16 C10 120.6(4) 2_656 . ?
C18 C17 C16 120.8(6) . . ?
C18 C17 H10 119.6 . . ?
C16 C17 H10 119.6 . . ?
C17 C18 C19 119.6(5) . . ?
C17 C18 H11 120.2 . . ?
C19 C18 H11 120.2 . . ?
C18 C19 C18 120.3(7) 2_656 . ?
C18 C19 C20 119.9(3) 2_656 . ?
C18 C19 C20 119.9(3) . . ?
N4 C20 C19 180.0 . . ?
C5 N1 C2 111.8(5) . . ?
C5 N1 Ni1 116.8(4) . . ?
C2 N1 Ni1 131.3(4) . . ?
C6 N2 C9 112.5(5) . . ?
C6 N2 Ni1 115.8(4) . . ?
C9 N2 Ni1 131.4(4) . . ?
C14 N3 C15 120.5(3) . . ?
C14 N3 C15 120.5(3) . 2_656 ?
C15 N3 C15 119.0(6) . 2_656 ?
N1 Ni1 N1 93.7(3) . 2_656 ?
N1 Ni1 N2 86.4(2) . . ?
N1 Ni1 N2 178.37(17) 2_656 . ?
N1 Ni1 N2 178.37(17) . 2_656 ?
N1 Ni1 N2 86.4(2) 2_656 2_656 ?
N2 Ni1 N2 93.6(3) . 2_656 ?

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
C2 C1 C2 N1 1.7(3) 2_656 . . . ?
C11 C1 C2 N1 -178.3(3) . . . . ?
C2 C1 C2 C3 -178.3(6) 2_656 . . . ?
C11 C1 C2 C3 1.7(6) . . . . ?
N1 C2 C3 C4 1.6(5) . . . . ?
C1 C2 C3 C4 -178.3(4) . . . . ?
C2 C3 C4 C5 -1.2(5) . . . . ?
C3 C4 C5 N1 0.4(5) . . . . ?
C3 C4 C5 C6 -176.6(6) . . . . ?
N1 C5 C6 N2 -2.7(5) . . . . ?
C4 C5 C6 N2 174.2(6) . . . . ?
N1 C5 C6 C7 173.6(6) . . . . ?
C4 C5 C6 C7 -9.5(11) . . . . ?
N2 C6 C7 C8 -0.7(5) . . . . ?
C5 C6 C7 C8 -177.1(6) . . . . ?
C6 C7 C8 C9 0.6(5) . . . . ?
C7 C8 C9 N2 -0.2(5) . . . . ?
C7 C8 C9 C10 176.6(5) . . . . ?
N2 C9 C10 C9 2.0(3) . . . 2_656 ?
C8 C9 C10 C9 -174.4(6) . . . 2_656 ?
N2 C9 C10 C16 -178.0(3) . . . . ?
C8 C9 C10 C16 5.6(6) . . . . ?
C2 C1 C11 C12 -129.6(4) . . . 2_656 ?
C2 C1 C11 C12 50.4(4) 2_656 . . 2_656 ?
C2 C1 C11 C12 50.4(4) . . . . ?
C2 C1 C11 C12 -129.6(4) 2_656 . . . ?
C12 C11 C12 C13 -1.7(4) 2_656 . . . ?
C1 C11 C12 C13 178.3(4) . . . . ?
C11 C12 C13 C14 3.4(8) . . . . ?
C12 C13 C14 N3 178.3(4) . . . . ?
C12 C13 C14 C13 -1.7(4) . . . 2_656 ?
C9 C10 C16 C17 -132.8(3) . . . . ?
C9 C10 C16 C17 47.2(3) 2_656 . . . ?
C9 C10 C16 C17 47.2(3) . . . 2_656 ?
C9 C10 C16 C17 -132.8(3) 2_656 . . 2_656 ?
C17 C16 C17 C18 -0.7(3) 2_656 . . . ?
C10 C16 C17 C18 179.3(3) . . . . ?
C16 C17 C18 C19 1.3(6) . . . . ?
C17 C18 C19 C18 -0.7(3) . . . 2_656 ?
C17 C18 C19 C20 179.3(3) . . . . ?
C4 C5 N1 C2 0.7(5) . . . . ?
C6 C5 N1 C2 178.7(4) . . . . ?
C4 C5 N1 Ni1 -177.4(3) . . . . ?
C6 C5 N1 Ni1 0.6(5) . . . . ?
C1 C2 N1 C5 178.5(4) . . . . ?
C3 C2 N1 C5 -1.4(6) . . . . ?
C1 C2 N1 Ni1 -3.7(7) . . . . ?
C3 C2 N1 Ni1 176.3(3) . . . . ?
C7 C6 N2 C9 0.6(6) . . . . ?
C5 C6 N2 C9 178.3(4) . . . . ?
C7 C6 N2 Ni1 -173.9(3) . . . . ?
C5 C6 N2 Ni1 3.8(5) . . . . ?
C10 C9 N2 C6 -177.6(4) . . . . ?
C8 C9 N2 C6 -0.3(6) . . . . ?
C10 C9 N2 Ni1 -4.3(7) . . . . ?
C8 C9 N2 Ni1 173.1(4) . . . . ?
C13 C14 N3 C15 7.1(4) . . . . ?
C13 C14 N3 C15 -172.9(4) 2_656 . . . ?
C13 C14 N3 C15 -172.9(4) . . . 2_656 ?
C13 C14 N3 C15 7.1(4) 2_656 . . 2_656 ?
C5 N1 Ni1 N1 179.6(4) . . . 2_656 ?
C2 N1 Ni1 N1 1.9(4) . . . 2_656 ?
C5 N1 Ni1 N2 1.2(4) . . . . ?
C2 N1 Ni1 N2 -176.5(5) . . . . ?
C6 N2 Ni1 N1 -3.0(4) . . . . ?
C9 N2 Ni1 N1 -176.1(5) . . . . ?
C6 N2 Ni1 N2 175.4(5) . . . 2_656 ?
C9 N2 Ni1 N2 2.2(4) . . . 2_656 ?

_refine_diff_density_max         1.264
_refine_diff_density_min         -1.341
_refine_diff_density_rms         0.141

_shelxl_version_number           2014-3



####################################################################### 
# 
# 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_shino150917yt_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1511824'
_audit_update_record             
;
2016-10-27 deposited with the CCDC.
2016-12-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C32 H23 N5 Ni'
_chemical_formula_weight         536.26

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   14.9222(10)
_cell_length_b                   10.1071(7)
_cell_length_c                   16.9856(11)
_cell_angle_alpha                90
_cell_angle_beta                 111.902(2)
_cell_angle_gamma                90
_cell_volume                     2376.9(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    93(2)
_cell_measurement_reflns_used    9951
_cell_measurement_theta_min      2.2918
_cell_measurement_theta_max      25.0134

_exptl_crystal_description       prism
_exptl_crystal_colour            purple
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.499
_exptl_crystal_F_000             1112
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.390
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    0.850
_shelx_estimated_absorpt_T_min   0.733
_shelx_estimated_absorpt_T_max   0.951
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.82
_exptl_absorpt_correction_T_max  0.95
_exptl_absorpt_process_details   'SADABS V2014/5 (Bruker AXS Inc.)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      93(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 QUEST'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_reflns_number            15030
_diffrn_reflns_av_unetI/netI     0.0196
_diffrn_reflns_av_R_equivalents  0.0211
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.292
_diffrn_reflns_theta_max         25.028
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.970
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.970
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.970
_reflns_number_total             4169
_reflns_number_gt                3639
_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       ?
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0336P)²+2.2738P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4169
_refine_ls_number_parameters     345
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0351
_refine_ls_R_factor_gt           0.0301
_refine_ls_wR_factor_ref         0.0819
_refine_ls_wR_factor_gt          0.0784
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_restrained_S_all      1.092
_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
C1 C 0.68924(13) 0.71436(19) 0.32592(11) 0.0148(4) Uani 1 1 d . . . . .
C2 C 0.63349(13) 0.60403(19) 0.27804(11) 0.0146(4) Uani 1 1 d . . . . .
C3 C 0.65407(13) 0.46764(19) 0.27003(12) 0.0172(4) Uani 1 1 d . . . . .
H1 H 0.7155 0.4266 0.2950 0.021 Uiso 1 1 calc R U . . .
C4 C 0.56882(13) 0.4052(2) 0.21941(12) 0.0185(4) Uani 1 1 d . . . . .
H2 H 0.5614 0.3147 0.2033 0.022 Uiso 1 1 calc R U . . .
C5 C 0.49566(13) 0.50222(19) 0.19673(11) 0.0160(4) Uani 1 1 d . . . . .
C6 C 0.38896(13) 0.51815(19) 0.15273(11) 0.0162(4) Uani 1 1 d . . . . .
C7 C 0.30364(13) 0.4453(2) 0.10765(12) 0.0195(4) Uani 1 1 d . . . . .
H3 H 0.3001 0.3543 0.0928 0.023 Uiso 1 1 calc R U . . .
C8 C 0.22658(13) 0.5323(2) 0.08946(12) 0.0188(4) Uani 1 1 d . . . . .
H4 H 0.1604 0.5111 0.0599 0.023 Uiso 1 1 calc R U . . .
C9 C 0.26416(13) 0.65967(19) 0.12296(11) 0.0156(4) Uani 1 1 d . . . . .
C10 C 0.22199(13) 0.7846(2) 0.12795(11) 0.0160(4) Uani 1 1 d . . . . .
C11 C 0.27633(13) 0.8947(2) 0.17488(12) 0.0170(4) Uani 1 1 d . . . . .
C12 C 0.25449(14) 1.0301(2) 0.18505(12) 0.0182(4) Uani 1 1 d . . . . .
H5 H 0.1924 1.0698 0.1621 0.022 Uiso 1 1 calc R U . . .
C13 C 0.33939(14) 1.0935(2) 0.23414(12) 0.0189(4) Uani 1 1 d . . . . .
H6 H 0.3462 1.1840 0.2504 0.023 Uiso 1 1 calc R U . . .
C14 C 0.41396(13) 0.99810(19) 0.25542(11) 0.0167(4) Uani 1 1 d . . . . .
C15 C 0.52062(13) 0.98223(19) 0.30012(11) 0.0162(4) Uani 1 1 d . . . . .
C16 C 0.60540(14) 1.05519(19) 0.34478(12) 0.0182(4) Uani 1 1 d . . . . .
H7 H 0.6088 1.1460 0.3602 0.022 Uiso 1 1 calc R U . . .
C17 C 0.68261(13) 0.96857(19) 0.36177(12) 0.0172(4) Uani 1 1 d . . . . .
H8 H 0.7488 0.9903 0.3905 0.021 Uiso 1 1 calc R U . . .
C18 C 0.64565(13) 0.84137(19) 0.32875(11) 0.0153(4) Uani 1 1 d . . . . .
C19 C 0.79227(13) 0.69903(19) 0.37410(11) 0.0145(4) Uani 1 1 d . . . . .
C20 C 0.85141(13) 0.61632(19) 0.34670(11) 0.0156(4) Uani 1 1 d . . . . .
H9 H 0.8226 0.5669 0.2959 0.019 Uiso 1 1 calc R U . . .
C21 C 0.94921(13) 0.60513(19) 0.39123(12) 0.0164(4) Uani 1 1 d . . . . .
H10 H 0.9862 0.5478 0.3709 0.020 Uiso 1 1 calc R U . . .
C22 C 0.99551(13) 0.67769(19) 0.46678(12) 0.0163(4) Uani 1 1 d . . . . .
C23 C 0.93611(14) 0.75572(18) 0.49686(12) 0.0168(4) Uani 1 1 d . . . . .
H11 H 0.9642 0.8019 0.5491 0.020 Uiso 1 1 calc R U . . .
C24 C 0.83848(14) 0.76548(18) 0.45155(12) 0.0162(4) Uani 1 1 d . . . . .
H12 H 0.8008 0.8191 0.4733 0.019 Uiso 1 1 calc R U . . .
C25 C 1.15256(13) 0.5839(2) 0.48250(13) 0.0219(4) Uani 1 1 d . . . . .
H13 H 1.1267 0.4939 0.4782 0.033 Uiso 1 1 calc R U . . .
H14 H 1.2189 0.5855 0.5243 0.033 Uiso 1 1 calc R U . . .
H15 H 1.1522 0.6116 0.4271 0.033 Uiso 1 1 calc R U . . .
C26 C 1.13832(15) 0.7530(2) 0.58491(14) 0.0270(5) Uani 1 1 d . . . . .
H16 H 1.1146 0.8442 0.5739 0.040 Uiso 1 1 calc R U . . .
H17 H 1.2085 0.7522 0.6006 0.040 Uiso 1 1 calc R U . . .
H18 H 1.1224 0.7161 0.6314 0.040 Uiso 1 1 calc R U . . .
N1 N 1.09303(11) 0.67385(17) 0.50905(10) 0.0187(4) Uani 1 1 d . . . . .
C27 C 0.11617(13) 0.8008(2) 0.08267(12) 0.0168(4) Uani 1 1 d . . . . .
C28 C 0.06104(13) 0.8676(2) 0.12101(12) 0.0189(4) Uani 1 1 d . . . . .
H19 H 0.0918 0.9041 0.1761 0.023 Uiso 1 1 calc R U . . .
C29 C -0.03802(14) 0.8812(2) 0.07951(13) 0.0229(4) Uani 1 1 d . . . . .
H20 H -0.0747 0.9275 0.1059 0.027 Uiso 1 1 calc R U . . .
C30 C -0.08337(14) 0.8270(2) -0.00057(13) 0.0246(5) Uani 1 1 d . . . . .
H21 H -0.1514 0.8347 -0.0286 0.029 Uiso 1 1 calc R U . . .
C31 C -0.02981(15) 0.7616(2) -0.03999(13) 0.0238(5) Uani 1 1 d . . . . .
H22 H -0.0610 0.7253 -0.0951 0.029 Uiso 1 1 calc R U . . .
C32 C 0.06954(14) 0.7492(2) 0.00124(12) 0.0195(4) Uani 1 1 d . . . . .
H23 H 0.1061 0.7052 -0.0262 0.023 Uiso 1 1 calc R U . . .
N2 N 0.53645(11) 0.61794(16) 0.23144(10) 0.0164(3) Uani 1 1 d . . . . .
N3 N 0.36283(11) 0.64300(16) 0.16005(10) 0.0164(3) Uani 1 1 d . . . . .
N4 N 0.37416(11) 0.88268(16) 0.22007(10) 0.0176(3) Uani 1 1 d . . . . .
N5 N 0.54724(11) 0.85723(16) 0.29210(10) 0.0165(3) Uani 1 1 d . . . . .
Ni1 Ni 0.45514(2) 0.75020(2) 0.22586(2) 0.01558(10) Uani 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
C1 C2 1.446(3) . ?
C1 C18 1.448(3) . ?
C1 C19 1.456(2) . ?
C2 N2 1.374(2) . ?
C2 C3 1.430(3) . ?
C3 C4 1.393(3) . ?
C3 H1 0.9500 . ?
C4 C5 1.410(3) . ?
C4 H2 0.9500 . ?
C5 N2 1.348(2) . ?
C5 C6 1.494(3) . ?
C6 N3 1.340(2) . ?
C6 C7 1.422(3) . ?
C7 C8 1.387(3) . ?
C7 H3 0.9500 . ?
C8 C9 1.435(3) . ?
C8 H4 0.9500 . ?
C9 N3 1.379(2) . ?
C9 C10 1.427(3) . ?
C10 C11 1.431(3) . ?
C10 C27 1.485(3) . ?
C11 N4 1.378(2) . ?
C11 C12 1.433(3) . ?
C12 C13 1.386(3) . ?
C12 H5 0.9500 . ?
C13 C14 1.413(3) . ?
C13 H6 0.9500 . ?
C14 N4 1.345(2) . ?
C14 C15 1.495(3) . ?
C15 N5 1.346(2) . ?
C15 C16 1.416(3) . ?
C16 C17 1.389(3) . ?
C16 H7 0.9500 . ?
C17 C18 1.429(3) . ?
C17 H8 0.9500 . ?
C18 N5 1.374(2) . ?
C19 C24 1.407(3) . ?
C19 C20 1.414(3) . ?
C20 C21 1.375(3) . ?
C20 H9 0.9500 . ?
C21 C22 1.414(3) . ?
C21 H10 0.9500 . ?
C22 N1 1.362(2) . ?
C22 C23 1.416(3) . ?
C23 C24 1.374(3) . ?
C23 H11 0.9500 . ?
C24 H12 0.9500 . ?
C25 N1 1.455(2) . ?
C25 H13 0.9800 . ?
C25 H14 0.9800 . ?
C25 H15 0.9800 . ?
C26 N1 1.452(3) . ?
C26 H16 0.9800 . ?
C26 H17 0.9800 . ?
C26 H18 0.9800 . ?
C27 C32 1.397(3) . ?
C27 C28 1.399(3) . ?
C28 C29 1.387(3) . ?
C28 H19 0.9500 . ?
C29 C30 1.386(3) . ?
C29 H20 0.9500 . ?
C30 C31 1.387(3) . ?
C30 H21 0.9500 . ?
C31 C32 1.389(3) . ?
C31 H22 0.9500 . ?
C32 H23 0.9500 . ?
N2 Ni1 1.7838(16) . ?
N3 Ni1 1.7810(16) . ?
N4 Ni1 1.7816(16) . ?
N5 Ni1 1.7808(16) . ?

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
C2 C1 C18 122.07(16) . . ?
C2 C1 C19 119.96(17) . . ?
C18 C1 C19 117.97(17) . . ?
N2 C2 C3 105.16(16) . . ?
N2 C2 C1 120.43(17) . . ?
C3 C2 C1 134.26(17) . . ?
C4 C3 C2 108.44(16) . . ?
C4 C3 H1 125.8 . . ?
C2 C3 H1 125.8 . . ?
C3 C4 C5 106.84(17) . . ?
C3 C4 H2 126.6 . . ?
C5 C4 H2 126.6 . . ?
N2 C5 C4 107.84(16) . . ?
N2 C5 C6 110.39(16) . . ?
C4 C5 C6 141.61(18) . . ?
N3 C6 C7 107.71(16) . . ?
N3 C6 C5 110.35(16) . . ?
C7 C6 C5 141.89(18) . . ?
C8 C7 C6 107.07(17) . . ?
C8 C7 H3 126.5 . . ?
C6 C7 H3 126.5 . . ?
C7 C8 C9 108.13(16) . . ?
C7 C8 H4 125.9 . . ?
C9 C8 H4 125.9 . . ?
N3 C9 C10 120.02(17) . . ?
N3 C9 C8 105.33(16) . . ?
C10 C9 C8 134.57(17) . . ?
C9 C10 C11 123.36(16) . . ?
C9 C10 C27 118.29(17) . . ?
C11 C10 C27 118.35(17) . . ?
N4 C11 C10 120.28(17) . . ?
N4 C11 C12 104.96(17) . . ?
C10 C11 C12 134.66(17) . . ?
C13 C12 C11 108.41(17) . . ?
C13 C12 H5 125.8 . . ?
C11 C12 H5 125.8 . . ?
C12 C13 C14 107.12(17) . . ?
C12 C13 H6 126.4 . . ?
C14 C13 H6 126.4 . . ?
N4 C14 C13 107.65(16) . . ?
N4 C14 C15 110.05(16) . . ?
C13 C14 C15 142.25(18) . . ?
N5 C15 C16 107.74(16) . . ?
N5 C15 C14 110.35(16) . . ?
C16 C15 C14 141.79(18) . . ?
C17 C16 C15 106.81(17) . . ?
C17 C16 H7 126.6 . . ?
C15 C16 H7 126.6 . . ?
C16 C17 C18 108.47(16) . . ?
C16 C17 H8 125.8 . . ?
C18 C17 H8 125.8 . . ?
N5 C18 C17 105.29(16) . . ?
N5 C18 C1 120.39(16) . . ?
C17 C18 C1 134.31(17) . . ?
C24 C19 C20 116.19(16) . . ?
C24 C19 C1 121.42(17) . . ?
C20 C19 C1 122.39(17) . . ?
C21 C20 C19 122.14(17) . . ?
C21 C20 H9 118.9 . . ?
C19 C20 H9 118.9 . . ?
C20 C21 C22 121.02(17) . . ?
C20 C21 H10 119.5 . . ?
C22 C21 H10 119.5 . . ?
N1 C22 C21 121.85(17) . . ?
N1 C22 C23 121.00(17) . . ?
C21 C22 C23 117.15(17) . . ?
C24 C23 C22 120.89(18) . . ?
C24 C23 H11 119.6 . . ?
C22 C23 H11 119.6 . . ?
C23 C24 C19 122.46(18) . . ?
C23 C24 H12 118.8 . . ?
C19 C24 H12 118.8 . . ?
N1 C25 H13 109.5 . . ?
N1 C25 H14 109.5 . . ?
H13 C25 H14 109.5 . . ?
N1 C25 H15 109.5 . . ?
H13 C25 H15 109.5 . . ?
H14 C25 H15 109.5 . . ?
N1 C26 H16 109.5 . . ?
N1 C26 H17 109.5 . . ?
H16 C26 H17 109.5 . . ?
N1 C26 H18 109.5 . . ?
H16 C26 H18 109.5 . . ?
H17 C26 H18 109.5 . . ?
C22 N1 C26 120.28(16) . . ?
C22 N1 C25 120.66(16) . . ?
C26 N1 C25 118.92(16) . . ?
C32 C27 C28 118.61(17) . . ?
C32 C27 C10 120.82(17) . . ?
C28 C27 C10 120.56(17) . . ?
C29 C28 C27 120.77(18) . . ?
C29 C28 H19 119.6 . . ?
C27 C28 H19 119.6 . . ?
C30 C29 C28 119.82(19) . . ?
C30 C29 H20 120.1 . . ?
C28 C29 H20 120.1 . . ?
C29 C30 C31 120.25(18) . . ?
C29 C30 H21 119.9 . . ?
C31 C30 H21 119.9 . . ?
C30 C31 C32 119.90(19) . . ?
C30 C31 H22 120.1 . . ?
C32 C31 H22 120.1 . . ?
C31 C32 C27 120.62(18) . . ?
C31 C32 H23 119.7 . . ?
C27 C32 H23 119.7 . . ?
C5 N2 C2 111.71(16) . . ?
C5 N2 Ni1 116.08(12) . . ?
C2 N2 Ni1 131.07(13) . . ?
C6 N3 C9 111.76(16) . . ?
C6 N3 Ni1 116.57(13) . . ?
C9 N3 Ni1 131.04(13) . . ?
C14 N4 C11 111.84(16) . . ?
C14 N4 Ni1 116.74(12) . . ?
C11 N4 Ni1 130.74(14) . . ?
C15 N5 C18 111.68(16) . . ?
C15 N5 Ni1 116.53(13) . . ?
C18 N5 Ni1 131.13(13) . . ?
N5 Ni1 N3 179.70(7) . . ?
N5 Ni1 N4 85.75(7) . . ?
N3 Ni1 N4 94.17(7) . . ?
N5 Ni1 N2 94.15(7) . . ?
N3 Ni1 N2 85.93(7) . . ?
N4 Ni1 N2 179.77(8) . . ?

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
C18 C1 C2 N2 1.6(3) . . . . ?
C19 C1 C2 N2 -179.14(16) . . . . ?
C18 C1 C2 C3 -173.08(19) . . . . ?
C19 C1 C2 C3 6.1(3) . . . . ?
N2 C2 C3 C4 -0.2(2) . . . . ?
C1 C2 C3 C4 175.1(2) . . . . ?
C2 C3 C4 C5 -0.5(2) . . . . ?
C3 C4 C5 N2 1.0(2) . . . . ?
C3 C4 C5 C6 -173.6(2) . . . . ?
N2 C5 C6 N3 -0.3(2) . . . . ?
C4 C5 C6 N3 174.2(2) . . . . ?
N2 C5 C6 C7 -177.2(2) . . . . ?
C4 C5 C6 C7 -2.7(5) . . . . ?
N3 C6 C7 C8 -0.4(2) . . . . ?
C5 C6 C7 C8 176.5(2) . . . . ?
C6 C7 C8 C9 0.3(2) . . . . ?
C7 C8 C9 N3 -0.1(2) . . . . ?
C7 C8 C9 C10 -176.5(2) . . . . ?
N3 C9 C10 C11 -4.2(3) . . . . ?
C8 C9 C10 C11 171.89(19) . . . . ?
N3 C9 C10 C27 176.31(16) . . . . ?
C8 C9 C10 C27 -7.6(3) . . . . ?
C9 C10 C11 N4 -1.6(3) . . . . ?
C27 C10 C11 N4 177.91(16) . . . . ?
C9 C10 C11 C12 174.31(19) . . . . ?
C27 C10 C11 C12 -6.2(3) . . . . ?
N4 C11 C12 C13 1.0(2) . . . . ?
C10 C11 C12 C13 -175.4(2) . . . . ?
C11 C12 C13 C14 -0.6(2) . . . . ?
C12 C13 C14 N4 0.0(2) . . . . ?
C12 C13 C14 C15 176.8(2) . . . . ?
N4 C14 C15 N5 0.4(2) . . . . ?
C13 C14 C15 N5 -176.4(2) . . . . ?
N4 C14 C15 C16 175.7(2) . . . . ?
C13 C14 C15 C16 -1.1(5) . . . . ?
N5 C15 C16 C17 0.6(2) . . . . ?
C14 C15 C16 C17 -174.8(2) . . . . ?
C15 C16 C17 C18 -0.8(2) . . . . ?
C16 C17 C18 N5 0.7(2) . . . . ?
C16 C17 C18 C1 179.18(19) . . . . ?
C2 C1 C18 N5 6.3(3) . . . . ?
C19 C1 C18 N5 -172.97(16) . . . . ?
C2 C1 C18 C17 -172.01(19) . . . . ?
C19 C1 C18 C17 8.8(3) . . . . ?
C2 C1 C19 C24 -145.83(18) . . . . ?
C18 C1 C19 C24 33.4(3) . . . . ?
C2 C1 C19 C20 33.6(3) . . . . ?
C18 C1 C19 C20 -147.18(17) . . . . ?
C24 C19 C20 C21 -2.5(3) . . . . ?
C1 C19 C20 C21 178.10(18) . . . . ?
C19 C20 C21 C22 -0.6(3) . . . . ?
C20 C21 C22 N1 -176.09(18) . . . . ?
C20 C21 C22 C23 3.6(3) . . . . ?
N1 C22 C23 C24 176.20(18) . . . . ?
C21 C22 C23 C24 -3.5(3) . . . . ?
C22 C23 C24 C19 0.4(3) . . . . ?
C20 C19 C24 C23 2.6(3) . . . . ?
C1 C19 C24 C23 -177.99(18) . . . . ?
C21 C22 N1 C26 178.00(18) . . . . ?
C23 C22 N1 C26 -1.7(3) . . . . ?
C21 C22 N1 C25 -6.3(3) . . . . ?
C23 C22 N1 C25 174.03(17) . . . . ?
C9 C10 C27 C32 -41.8(3) . . . . ?
C11 C10 C27 C32 138.72(19) . . . . ?
C9 C10 C27 C28 137.92(19) . . . . ?
C11 C10 C27 C28 -41.6(3) . . . . ?
C32 C27 C28 C29 0.7(3) . . . . ?
C10 C27 C28 C29 -178.99(18) . . . . ?
C27 C28 C29 C30 0.6(3) . . . . ?
C28 C29 C30 C31 -1.3(3) . . . . ?
C29 C30 C31 C32 0.6(3) . . . . ?
C30 C31 C32 C27 0.7(3) . . . . ?
C28 C27 C32 C31 -1.3(3) . . . . ?
C10 C27 C32 C31 178.33(19) . . . . ?
C4 C5 N2 C2 -1.2(2) . . . . ?
C6 C5 N2 C2 175.23(15) . . . . ?
C4 C5 N2 Ni1 -170.36(12) . . . . ?
C6 C5 N2 Ni1 6.0(2) . . . . ?
C3 C2 N2 C5 0.9(2) . . . . ?
C1 C2 N2 C5 -175.21(16) . . . . ?
C3 C2 N2 Ni1 167.96(14) . . . . ?
C1 C2 N2 Ni1 -8.1(3) . . . . ?
C7 C6 N3 C9 0.4(2) . . . . ?
C5 C6 N3 C9 -177.58(15) . . . . ?
C7 C6 N3 Ni1 172.32(12) . . . . ?
C5 C6 N3 Ni1 -5.7(2) . . . . ?
C10 C9 N3 C6 176.89(16) . . . . ?
C8 C9 N3 C6 -0.2(2) . . . . ?
C10 C9 N3 Ni1 6.5(3) . . . . ?
C8 C9 N3 Ni1 -170.62(13) . . . . ?
C13 C14 N4 C11 0.7(2) . . . . ?
C15 C14 N4 C11 -177.23(15) . . . . ?
C13 C14 N4 Ni1 172.27(12) . . . . ?
C15 C14 N4 Ni1 -5.6(2) . . . . ?
C10 C11 N4 C14 175.95(17) . . . . ?
C12 C11 N4 C14 -1.0(2) . . . . ?
C10 C11 N4 Ni1 5.9(3) . . . . ?
C12 C11 N4 Ni1 -171.09(14) . . . . ?
C16 C15 N5 C18 -0.2(2) . . . . ?
C14 C15 N5 C18 176.79(15) . . . . ?
C16 C15 N5 Ni1 -171.95(12) . . . . ?
C14 C15 N5 Ni1 5.0(2) . . . . ?
C17 C18 N5 C15 -0.3(2) . . . . ?
C1 C18 N5 C15 -179.06(16) . . . . ?
C17 C18 N5 Ni1 169.89(14) . . . . ?
C1 C18 N5 Ni1 -8.8(3) . . . . ?
C15 N5 Ni1 N4 -6.68(14) . . . . ?
C18 N5 Ni1 N4 -176.53(18) . . . . ?
C15 N5 Ni1 N2 173.11(14) . . . . ?
C18 N5 Ni1 N2 3.26(17) . . . . ?
C6 N3 Ni1 N4 -172.75(14) . . . . ?
C9 N3 Ni1 N4 -2.72(17) . . . . ?
C6 N3 Ni1 N2 7.45(14) . . . . ?
C9 N3 Ni1 N2 177.48(17) . . . . ?
C14 N4 Ni1 N5 6.96(14) . . . . ?
C11 N4 Ni1 N5 176.63(18) . . . . ?
C14 N4 Ni1 N3 -173.33(14) . . . . ?
C11 N4 Ni1 N3 -3.66(18) . . . . ?
C5 N2 Ni1 N5 172.14(14) . . . . ?
C2 N2 Ni1 N5 5.52(17) . . . . ?
C5 N2 Ni1 N3 -7.57(14) . . . . ?
C2 N2 Ni1 N3 -174.19(18) . . . . ?

_refine_diff_density_max         0.288
_refine_diff_density_min         -0.384
_refine_diff_density_rms         0.053

_shelxl_version_number           2014-3



####################################################################### 
# 
# 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_shino_150710_NMeC6F5nor_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1511827'
_audit_update_record             
;
2016-10-27 deposited with the CCDC.
2016-12-20 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 H18 Cl2 F5 N5 Ni'
_chemical_formula_weight         697.12

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'
F F 0.0171 0.0103 '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'
Cl Cl 0.1484 0.1585 '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                   16.003(2)
_cell_length_b                   10.6329(14)
_cell_length_c                   17.070(2)
_cell_angle_alpha                90
_cell_angle_beta                 100.125(4)
_cell_angle_gamma                90
_cell_volume                     2859.4(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    93(2)
_cell_measurement_reflns_used    8006
_cell_measurement_theta_min      2.2666
_cell_measurement_theta_max      25.0494

_exptl_crystal_description       prism
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.619
_exptl_crystal_F_000             1408
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.245
_exptl_crystal_size_mid          0.236
_exptl_crystal_size_min          0.021
_exptl_absorpt_coefficient_mu    0.932
_shelx_estimated_absorpt_T_min   0.804
_shelx_estimated_absorpt_T_max   0.981
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.69
_exptl_absorpt_correction_T_max  0.98
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      93(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 QUEST'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_reflns_number            15105
_diffrn_reflns_av_unetI/netI     0.0561
_diffrn_reflns_av_R_equivalents  0.0472
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.267
_diffrn_reflns_theta_max         25.070
_diffrn_reflns_theta_full        25.070
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measured_fraction_theta_full 0.978
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_Laue_measured_fraction_full 0.978
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_point_group_measured_fraction_full 0.978
_reflns_number_total             4967
_reflns_number_gt                3820
_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       ?
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0246P)²+15.9652P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4967
_refine_ls_number_parameters     417
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0940
_refine_ls_R_factor_gt           0.0694
_refine_ls_wR_factor_ref         0.1479
_refine_ls_wR_factor_gt          0.1374
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_restrained_S_all      1.078
_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
C2 C 0.4934(3) 0.4503(5) 0.7187(3) 0.0250(11) Uani 1 1 d . . . . .
C3 C 0.5138(4) 0.3932(5) 0.6473(3) 0.0317(13) Uani 1 1 d . . . . .
C4 C 0.5870(4) 0.3421(5) 0.6248(3) 0.0326(13) Uani 1 1 d . . . . .
H4 H 0.6403 0.3336 0.6591 0.039 Uiso 1 1 calc R U . . .
C5 C 0.5709(3) 0.3057(5) 0.5457(4) 0.0333(13) Uani 1 1 d . . . . .
H5 H 0.6096 0.2674 0.5168 0.040 Uiso 1 1 calc R U . . .
C6 C 0.4844(3) 0.3374(5) 0.5165(3) 0.0298(13) Uani 1 1 d . . . . .
C7 C 0.4197(3) 0.3391(5) 0.4408(3) 0.0270(12) Uani 1 1 d . . . . .
C8 C 0.4056(3) 0.3067(5) 0.3590(3) 0.0290(12) Uani 1 1 d . . . . .
H8 H 0.4450 0.2666 0.3315 0.035 Uiso 1 1 calc R U . . .
C9 C 0.3243(3) 0.3440(5) 0.3263(3) 0.0277(12) Uani 1 1 d . . . . .
H9 H 0.2978 0.3331 0.2725 0.033 Uiso 1 1 calc R U . . .
C10 C 0.2871(3) 0.4015(5) 0.3871(3) 0.0255(12) Uani 1 1 d . . . . .
C11 C 0.2085(3) 0.4581(5) 0.3930(3) 0.0207(11) Uani 1 1 d . . . . .
C12 C 0.1864(3) 0.5100(5) 0.4628(3) 0.0249(12) Uani 1 1 d . . . . .
C13 C 0.1100(3) 0.5613(5) 0.4826(3) 0.0266(12) Uani 1 1 d . . . . .
H13 H 0.0578 0.5722 0.4469 0.032 Uiso 1 1 calc R U . . .
C14 C 0.1256(3) 0.5925(5) 0.5630(3) 0.0278(12) Uani 1 1 d . . . . .
H14 H 0.0861 0.6279 0.5924 0.033 Uiso 1 1 calc R U . . .
C15 C 0.2118(3) 0.5612(5) 0.5930(3) 0.0266(12) Uani 1 1 d . . . . .
C16 C 0.2766(3) 0.5580(5) 0.6676(3) 0.0267(12) Uani 1 1 d . . . . .
C17 C 0.2867(3) 0.5782(5) 0.7502(3) 0.0259(12) Uani 1 1 d . . . . .
H17 H 0.2450 0.6096 0.7784 0.031 Uiso 1 1 calc R U . . .
C18 C 0.3696(3) 0.5436(5) 0.7827(3) 0.0276(12) Uani 1 1 d . . . . .
H18 H 0.3943 0.5470 0.8375 0.033 Uiso 1 1 calc R U . . .
C19 C 0.4108(3) 0.5023(5) 0.7204(3) 0.0235(11) Uani 1 1 d . . . . .
C20 C 0.5563(3) 0.4561(5) 0.7913(3) 0.0274(12) Uani 1 1 d . . . . .
C21 C 0.5642(3) 0.5628(5) 0.8409(3) 0.0287(12) Uani 1 1 d . . . . .
H21 H 0.5276 0.6324 0.8261 0.034 Uiso 1 1 calc R U . . .
C22 C 0.6229(3) 0.5699(5) 0.9101(3) 0.0319(13) Uani 1 1 d . . . . .
H22 H 0.6270 0.6444 0.9413 0.038 Uiso 1 1 calc R U . . .
C23 C 0.6771(3) 0.4675(5) 0.9353(3) 0.0328(13) Uani 1 1 d . . . . .
C24 C 0.6708(3) 0.3617(5) 0.8854(3) 0.0325(13) Uani 1 1 d . . . . .
H24 H 0.7071 0.2918 0.9001 0.039 Uiso 1 1 calc R U . . .
C25 C 0.6131(3) 0.3575(5) 0.8156(3) 0.0297(13) Uani 1 1 d . . . . .
H25 H 0.6116 0.2852 0.7826 0.036 Uiso 1 1 calc R U . . .
C26 C 0.1418(3) 0.4674(5) 0.3196(3) 0.0236(11) Uani 1 1 d . . . . .
C27 C 0.1489(3) 0.5517(5) 0.2596(3) 0.0268(12) Uani 1 1 d . . . . .
C28 C 0.0854(3) 0.5676(5) 0.1939(3) 0.0292(12) Uani 1 1 d . . . . .
C29 C 0.0108(3) 0.5011(5) 0.1893(3) 0.0306(13) Uani 1 1 d . . . . .
C30 C 0.0021(3) 0.4167(5) 0.2475(3) 0.0279(12) Uani 1 1 d . . . . .
C31 C 0.0669(3) 0.3997(5) 0.3120(3) 0.0279(12) Uani 1 1 d . . . . .
C32 C 0.7903(3) 0.3669(5) 1.0300(3) 0.0343(14) Uani 1 1 d . . . . .
H32A H 0.7587 0.2876 1.0246 0.051 Uiso 1 1 calc R U . . .
H32B H 0.8178 0.3781 1.0856 0.051 Uiso 1 1 calc R U . . .
H32C H 0.8336 0.3650 0.9960 0.051 Uiso 1 1 calc R U . . .
C33 C 0.7389(4) 0.5814(5) 1.0572(3) 0.0366(14) Uani 1 1 d . . . . .
H33A H 0.7578 0.6533 1.0289 0.055 Uiso 1 1 calc R U . . .
H33B H 0.7801 0.5656 1.1059 0.055 Uiso 1 1 calc R U . . .
H33C H 0.6833 0.5999 1.0710 0.055 Uiso 1 1 calc R U . . .
C34 C 0.1476(5) 0.2424(7) 0.0988(5) 0.069(2) Uani 1 1 d . . . . .
H34A H 0.1993 0.2943 0.1137 0.083 Uiso 1 1 calc R U . . .
H34B H 0.1618 0.1717 0.0658 0.083 Uiso 1 1 calc R U . . .
Cl1 Cl 0.11832(15) 0.18145(18) 0.18614(11) 0.0708(6) Uani 1 1 d . . . . .
Cl2 Cl 0.06981(14) 0.3324(2) 0.04294(10) 0.0709(6) Uani 1 1 d . . . . .
F1 F 0.2180(2) 0.6233(3) 0.26409(19) 0.0400(8) Uani 1 1 d . . . . .
F2 F 0.0951(2) 0.6476(3) 0.13589(19) 0.0402(8) Uani 1 1 d . . . . .
F3 F -0.0519(2) 0.5174(3) 0.12667(18) 0.0412(9) Uani 1 1 d . . . . .
F4 F -0.07043(19) 0.3485(3) 0.2411(2) 0.0422(9) Uani 1 1 d . . . . .
F5 F 0.05633(19) 0.3139(3) 0.36601(18) 0.0347(8) Uani 1 1 d . . . . .
N1 N 0.4541(3) 0.3866(4) 0.5770(3) 0.0281(10) Uani 1 1 d . . . . .
N2 N 0.3481(2) 0.3931(4) 0.4554(2) 0.0245(10) Uani 1 1 d . . . . .
N3 N 0.2449(3) 0.5143(4) 0.5321(2) 0.0263(10) Uani 1 1 d . . . . .
N4 N 0.3507(3) 0.5129(4) 0.6515(2) 0.0275(10) Uani 1 1 d . . . . .
N5 N 0.7325(3) 0.4705(4) 1.0064(3) 0.0384(12) Uani 1 1 d . . . . .
Ni1 Ni 0.35080(4) 0.45464(6) 0.55343(4) 0.0259(2) Uani 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
C2 C19 1.437(7) . ?
C2 C3 1.450(8) . ?
C2 C20 1.454(7) . ?
C3 N1 1.398(7) . ?
C3 C4 1.405(8) . ?
C4 C5 1.384(8) . ?
C4 H4 0.9500 . ?
C5 C6 1.427(7) . ?
C5 H5 0.9500 . ?
C6 N1 1.325(7) . ?
C6 C7 1.507(7) . ?
C7 N2 1.343(7) . ?
C7 C8 1.417(8) . ?
C8 C9 1.380(7) . ?
C8 H8 0.9500 . ?
C9 C10 1.423(7) . ?
C9 H9 0.9500 . ?
C10 N2 1.385(6) . ?
C10 C11 1.413(7) . ?
C11 C12 1.413(7) . ?
C11 C26 1.501(6) . ?
C12 N3 1.374(6) . ?
C12 C13 1.432(7) . ?
C13 C14 1.392(7) . ?
C13 H13 0.9500 . ?
C14 C15 1.423(7) . ?
C14 H14 0.9500 . ?
C15 N3 1.343(7) . ?
C15 C16 1.495(7) . ?
C16 N4 1.351(7) . ?
C16 C17 1.408(7) . ?
C17 C18 1.394(7) . ?
C17 H17 0.9500 . ?
C18 C19 1.417(7) . ?
C18 H18 0.9500 . ?
C19 N4 1.386(6) . ?
C20 C25 1.401(7) . ?
C20 C21 1.409(7) . ?
C21 C22 1.376(7) . ?
C21 H21 0.9500 . ?
C22 C23 1.411(8) . ?
C22 H22 0.9500 . ?
C23 N5 1.371(7) . ?
C23 C24 1.404(8) . ?
C24 C25 1.375(7) . ?
C24 H24 0.9500 . ?
C25 H25 0.9500 . ?
C26 C27 1.380(7) . ?
C26 C31 1.384(7) . ?
C27 F1 1.333(6) . ?
C27 C28 1.386(7) . ?
C28 F2 1.334(6) . ?
C28 C29 1.378(8) . ?
C29 F3 1.343(6) . ?
C29 C30 1.365(8) . ?
C30 F4 1.356(6) . ?
C30 C31 1.386(7) . ?
C31 F5 1.328(6) . ?
C32 N5 1.450(7) . ?
C32 H32A 0.9800 . ?
C32 H32B 0.9800 . ?
C32 H32C 0.9800 . ?
C33 N5 1.456(7) . ?
C33 H33A 0.9800 . ?
C33 H33B 0.9800 . ?
C33 H33C 0.9800 . ?
C34 Cl2 1.720(8) . ?
C34 Cl1 1.763(8) . ?
C34 H34A 0.9900 . ?
C34 H34B 0.9900 . ?
N1 Ni1 1.784(4) . ?
N2 Ni1 1.791(4) . ?
N3 Ni1 1.786(4) . ?
N4 Ni1 1.785(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C19 C2 C3 121.4(5) . . ?
C19 C2 C20 118.0(5) . . ?
C3 C2 C20 120.6(5) . . ?
N1 C3 C4 102.9(5) . . ?
N1 C3 C2 121.4(5) . . ?
C4 C3 C2 135.6(5) . . ?
C5 C4 C3 110.7(5) . . ?
C5 C4 H4 124.6 . . ?
C3 C4 H4 124.6 . . ?
C4 C5 C6 106.2(5) . . ?
C4 C5 H5 126.9 . . ?
C6 C5 H5 126.9 . . ?
N1 C6 C5 106.6(5) . . ?
N1 C6 C7 112.0(4) . . ?
C5 C6 C7 141.3(6) . . ?
N2 C7 C8 107.1(4) . . ?
N2 C7 C6 109.0(5) . . ?
C8 C7 C6 143.9(5) . . ?
C9 C8 C7 107.6(5) . . ?
C9 C8 H8 126.2 . . ?
C7 C8 H8 126.2 . . ?
C8 C9 C10 108.4(5) . . ?
C8 C9 H9 125.8 . . ?
C10 C9 H9 125.8 . . ?
N2 C10 C11 118.2(5) . . ?
N2 C10 C9 105.2(4) . . ?
C11 C10 C9 136.6(5) . . ?
C10 C11 C12 125.8(4) . . ?
C10 C11 C26 118.7(4) . . ?
C12 C11 C26 115.6(4) . . ?
N3 C12 C11 120.3(5) . . ?
N3 C12 C13 105.4(4) . . ?
C11 C12 C13 134.3(5) . . ?
C14 C13 C12 108.1(5) . . ?
C14 C13 H13 125.9 . . ?
C12 C13 H13 125.9 . . ?
C13 C14 C15 107.0(5) . . ?
C13 C14 H14 126.5 . . ?
C15 C14 H14 126.5 . . ?
N3 C15 C14 107.4(4) . . ?
N3 C15 C16 109.9(5) . . ?
C14 C15 C16 142.7(5) . . ?
N4 C16 C17 107.9(4) . . ?
N4 C16 C15 109.8(4) . . ?
C17 C16 C15 142.2(5) . . ?
C18 C17 C16 107.0(5) . . ?
C18 C17 H17 126.5 . . ?
C16 C17 H17 126.5 . . ?
C17 C18 C19 108.5(4) . . ?
C17 C18 H18 125.7 . . ?
C19 C18 H18 125.7 . . ?
N4 C19 C18 105.5(4) . . ?
N4 C19 C2 121.2(5) . . ?
C18 C19 C2 133.2(5) . . ?
C25 C20 C21 116.1(5) . . ?
C25 C20 C2 122.5(5) . . ?
C21 C20 C2 121.4(5) . . ?
C22 C21 C20 122.4(5) . . ?
C22 C21 H21 118.8 . . ?
C20 C21 H21 118.8 . . ?
C21 C22 C23 120.7(5) . . ?
C21 C22 H22 119.7 . . ?
C23 C22 H22 119.7 . . ?
N5 C23 C24 121.5(5) . . ?
N5 C23 C22 121.3(5) . . ?
C24 C23 C22 117.3(5) . . ?
C25 C24 C23 121.2(5) . . ?
C25 C24 H24 119.4 . . ?
C23 C24 H24 119.4 . . ?
C24 C25 C20 122.3(5) . . ?
C24 C25 H25 118.9 . . ?
C20 C25 H25 118.9 . . ?
C27 C26 C31 116.9(4) . . ?
C27 C26 C11 121.5(4) . . ?
C31 C26 C11 121.4(5) . . ?
F1 C27 C26 120.3(4) . . ?
F1 C27 C28 117.3(5) . . ?
C26 C27 C28 122.3(5) . . ?
F2 C28 C29 119.8(5) . . ?
F2 C28 C27 120.9(5) . . ?
C29 C28 C27 119.2(5) . . ?
F3 C29 C30 120.4(5) . . ?
F3 C29 C28 119.9(5) . . ?
C30 C29 C28 119.7(5) . . ?
F4 C30 C29 119.3(5) . . ?
F4 C30 C31 120.3(5) . . ?
C29 C30 C31 120.4(5) . . ?
F5 C31 C26 120.4(5) . . ?
F5 C31 C30 118.2(5) . . ?
C26 C31 C30 121.4(5) . . ?
N5 C32 H32A 109.5 . . ?
N5 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
N5 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
N5 C33 H33A 109.5 . . ?
N5 C33 H33B 109.5 . . ?
H33A C33 H33B 109.5 . . ?
N5 C33 H33C 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
Cl2 C34 Cl1 113.6(4) . . ?
Cl2 C34 H34A 108.9 . . ?
Cl1 C34 H34A 108.9 . . ?
Cl2 C34 H34B 108.9 . . ?
Cl1 C34 H34B 108.9 . . ?
H34A C34 H34B 107.7 . . ?
C6 N1 C3 113.6(4) . . ?
C6 N1 Ni1 115.8(3) . . ?
C3 N1 Ni1 129.8(4) . . ?
C7 N2 C10 111.7(4) . . ?
C7 N2 Ni1 116.7(3) . . ?
C10 N2 Ni1 131.3(4) . . ?
C15 N3 C12 112.1(4) . . ?
C15 N3 Ni1 117.7(3) . . ?
C12 N3 Ni1 130.0(4) . . ?
C16 N4 C19 111.1(4) . . ?
C16 N4 Ni1 117.3(3) . . ?
C19 N4 Ni1 130.7(4) . . ?
C23 N5 C32 120.7(5) . . ?
C23 N5 C33 120.9(5) . . ?
C32 N5 C33 118.3(4) . . ?
N1 Ni1 N4 94.7(2) . . ?
N1 Ni1 N3 176.5(2) . . ?
N4 Ni1 N3 84.9(2) . . ?
N1 Ni1 N2 86.09(19) . . ?
N4 Ni1 N2 178.2(2) . . ?
N3 Ni1 N2 94.22(19) . . ?

_refine_diff_density_max         0.716
_refine_diff_density_min         -0.633
_refine_diff_density_rms         0.092



####################################################################### 
# 
# 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_SHELXL
_database_code_depnum_ccdc_archive 'CCDC 1511823'
_audit_update_record             
;
2016-10-27 deposited with the CCDC.
2016-12-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C35 H29 N5 Ni'
_chemical_formula_weight         578.34

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   11.547(4)
_cell_length_b                   7.327(2)
_cell_length_c                   32.081(9)
_cell_angle_alpha                90
_cell_angle_beta                 96.234(5)
_cell_angle_gamma                90
_cell_volume                     2698.4(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    118(2)
_cell_measurement_reflns_used    11007
_cell_measurement_theta_min      1.95
_cell_measurement_theta_max      31.63

_exptl_crystal_description       prism
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.424
_exptl_crystal_F_000             1208
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.370
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.070
_exptl_absorpt_coefficient_mu    0.754
_shelx_estimated_absorpt_T_min   0.768
_shelx_estimated_absorpt_T_max   0.949
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.824
_exptl_absorpt_correction_T_max  0.951
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      118(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Rigaku Saturn724'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 7.111
_diffrn_reflns_number            17385
_diffrn_reflns_av_unetI/netI     0.0225
_diffrn_reflns_av_R_equivalents  0.0240
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_theta_min         2.070
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.967
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.967
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.967
_reflns_number_total             4731
_reflns_number_gt                4528
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0552P)²+1.3661P] 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_number_reflns         4731
_refine_ls_number_parameters     375
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0333
_refine_ls_R_factor_gt           0.0320
_refine_ls_wR_factor_ref         0.0917
_refine_ls_wR_factor_gt          0.0903
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_restrained_S_all      1.077
_refine_ls_shift/su_max          0.004
_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
C1 C 0.60796(16) 0.2343(2) 0.76584(6) 0.0196(4) Uani 1 1 d . . . . .
C2 C 0.59692(15) 0.1922(2) 0.80937(5) 0.0206(3) Uani 1 1 d . . . . .
C3 C 0.50225(15) 0.1415(2) 0.83217(5) 0.0256(4) Uani 1 1 d . . . . .
H1 H 0.4232 0.1289 0.8208 0.031 Uiso 1 1 calc R U . . .
C4 C 0.54535(15) 0.1136(3) 0.87381(5) 0.0266(4) Uani 1 1 d . . . . .
H2 H 0.5014 0.0813 0.8961 0.032 Uiso 1 1 calc R U . . .
C5 C 0.66649(15) 0.1425(2) 0.87675(5) 0.0213(3) Uani 1 1 d . . . . .
C6 C 0.77326(15) 0.1375(2) 0.90697(5) 0.0215(3) Uani 1 1 d . . . . .
C7 C 0.81330(15) 0.1089(2) 0.94997(5) 0.0251(4) Uani 1 1 d . . . . .
H3 H 0.7671 0.0750 0.9715 0.030 Uiso 1 1 calc R U . . .
C8 C 0.93254(15) 0.1399(2) 0.95466(5) 0.0246(4) Uani 1 1 d . . . . .
H4 H 0.9828 0.1307 0.9801 0.030 Uiso 1 1 calc R U . . .
C9 C 0.96650(15) 0.1882(2) 0.91450(5) 0.0222(4) Uani 1 1 d . . . . .
C10 C 1.07313(16) 0.2476(2) 0.90048(6) 0.0211(4) Uani 1 1 d . . . . .
C11 C 1.08496(15) 0.2962(2) 0.85859(5) 0.0211(4) Uani 1 1 d . . . . .
C12 C 1.17496(15) 0.3855(2) 0.83846(5) 0.0234(4) Uani 1 1 d . . . . .
H5 H 1.2508 0.4148 0.8512 0.028 Uiso 1 1 calc R U . . .
C13 C 1.13214(14) 0.4213(2) 0.79741(5) 0.0224(4) Uani 1 1 d . . . . .
H6 H 1.1724 0.4807 0.7770 0.027 Uiso 1 1 calc R U . . .
C14 C 1.01600(14) 0.3521(2) 0.79152(5) 0.0203(3) Uani 1 1 d . . . . .
C15 C 0.91045(14) 0.3489(2) 0.76042(5) 0.0200(3) Uani 1 1 d . . . . .
C16 C 0.86888(15) 0.4062(2) 0.71953(5) 0.0220(3) Uani 1 1 d . . . . .
H7 H 0.9132 0.4611 0.6996 0.026 Uiso 1 1 calc R U . . .
C17 C 0.75050(15) 0.3665(2) 0.71398(5) 0.0216(3) Uani 1 1 d . . . . .
H8 H 0.6993 0.3901 0.6893 0.026 Uiso 1 1 calc R U . . .
C18 C 0.71861(15) 0.2843(2) 0.75157(5) 0.0201(3) Uani 1 1 d . . . . .
C19 C 0.50657(16) 0.2249(2) 0.73502(5) 0.0204(4) Uani 1 1 d . . . . .
C20 C 0.51577(15) 0.1620(2) 0.69381(5) 0.0219(3) Uani 1 1 d . . . . .
H11 H 0.5905 0.1305 0.6862 0.026 Uiso 1 1 calc R U . . .
C21 C 0.42087(15) 0.1448(2) 0.66450(5) 0.0235(4) Uani 1 1 d . . . . .
H12 H 0.4308 0.0994 0.6374 0.028 Uiso 1 1 calc R U . . .
C22 C 0.30825(16) 0.1938(2) 0.67405(5) 0.0230(4) Uani 1 1 d . . . . .
C23 C 0.29795(16) 0.2572(2) 0.71512(6) 0.0231(4) Uani 1 1 d . . . . .
H13 H 0.2236 0.2912 0.7226 0.028 Uiso 1 1 calc R U . . .
C24 C 0.39354(16) 0.2706(2) 0.74426(5) 0.0211(4) Uani 1 1 d . . . . .
H14 H 0.3833 0.3122 0.7717 0.025 Uiso 1 1 calc R U . . .
C25 C 0.22525(17) 0.1374(3) 0.60166(6) 0.0341(4) Uani 1 1 d . . . . .
H15 H 0.2723 0.2319 0.5900 0.051 Uiso 1 1 calc R U . . .
H16 H 0.1480 0.1329 0.5857 0.051 Uiso 1 1 calc R U . . .
H17 H 0.2637 0.0187 0.6000 0.051 Uiso 1 1 calc R U . . .
C26 C 0.09793(17) 0.2304(3) 0.65588(7) 0.0329(4) Uani 1 1 d . . . . .
H18 H 0.0828 0.1690 0.6819 0.049 Uiso 1 1 calc R U . . .
H19 H 0.0390 0.1935 0.6331 0.049 Uiso 1 1 calc R U . . .
H20 H 0.0945 0.3629 0.6598 0.049 Uiso 1 1 calc R U . . .
C27 C 1.17539(16) 0.2669(2) 0.93334(6) 0.0222(4) Uani 1 1 d . . . . .
C28 C 1.26096(14) 0.1309(2) 0.93796(5) 0.0239(4) Uani 1 1 d . . . . .
C29 C 1.35184(15) 0.1488(3) 0.96988(5) 0.0267(4) Uani 1 1 d . . . . .
H9 H 1.4102 0.0569 0.9732 0.032 Uiso 1 1 calc R U . . .
C30 C 1.35992(16) 0.2971(3) 0.99708(6) 0.0271(4) Uani 1 1 d . . . . .
C31 C 1.27459(15) 0.4311(3) 0.99157(5) 0.0273(4) Uani 1 1 d . . . . .
H10 H 1.2792 0.5333 1.0099 0.033 Uiso 1 1 calc R U . . .
C32 C 1.18235(15) 0.4194(2) 0.95985(5) 0.0246(4) Uani 1 1 d . . . . .
C33 C 1.09349(17) 0.5699(3) 0.95421(6) 0.0331(4) Uani 1 1 d . . . . .
H21 H 1.1219 0.6761 0.9709 0.050 Uiso 1 1 calc R U . . .
H22 H 1.0201 0.5277 0.9636 0.050 Uiso 1 1 calc R U . . .
H23 H 1.0806 0.6040 0.9245 0.050 Uiso 1 1 calc R U . . .
C34 C 1.25511(16) -0.0327(3) 0.90908(6) 0.0325(4) Uani 1 1 d . . . . .
H24 H 1.2805 0.0029 0.8821 0.049 Uiso 1 1 calc R U . . .
H25 H 1.1748 -0.0779 0.9047 0.049 Uiso 1 1 calc R U . . .
H26 H 1.3062 -0.1292 0.9217 0.049 Uiso 1 1 calc R U . . .
C35 C 1.45904(17) 0.3117(3) 1.03184(6) 0.0360(5) Uani 1 1 d . . . . .
H27 H 1.4516 0.2153 1.0526 0.054 Uiso 1 1 calc R U . . .
H28 H 1.4564 0.4312 1.0454 0.054 Uiso 1 1 calc R U . . .
H29 H 1.5334 0.2982 1.0201 0.054 Uiso 1 1 calc R U . . .
N1 N 0.81930(13) 0.27584(19) 0.77803(4) 0.0202(3) Uani 1 1 d . . . . .
N2 N 0.69307(12) 0.18978(19) 0.83813(4) 0.0210(3) Uani 1 1 d . . . . .
N3 N 0.86674(12) 0.1816(2) 0.88739(4) 0.0216(3) Uani 1 1 d . . . . .
N4 N 0.99265(13) 0.27716(19) 0.82788(5) 0.0206(3) Uani 1 1 d . . . . .
N5 N 0.21304(13) 0.1797(2) 0.64528(5) 0.0292(3) Uani 1 1 d . . . . .
Ni1 Ni 0.84335(2) 0.22466(3) 0.83252(2) 0.01929(10) Uani 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
C1 C2 1.450(2) . ?
C1 C19 1.450(2) . ?
C1 C18 1.450(3) . ?
C2 N2 1.364(2) . ?
C2 C3 1.429(2) . ?
C3 C4 1.389(3) . ?
C3 H1 0.9500 . ?
C4 C5 1.408(2) . ?
C4 H2 0.9500 . ?
C5 N2 1.353(2) . ?
C5 C6 1.484(2) . ?
C6 N3 1.346(2) . ?
C6 C7 1.422(2) . ?
C7 C8 1.388(3) . ?
C7 H3 0.9500 . ?
C8 C9 1.431(2) . ?
C8 H4 0.9500 . ?
C9 N3 1.367(2) . ?
C9 C10 1.424(3) . ?
C10 C11 1.411(3) . ?
C10 C27 1.502(2) . ?
C11 N4 1.378(2) . ?
C11 C12 1.439(2) . ?
C12 C13 1.381(2) . ?
C12 H5 0.9500 . ?
C13 C14 1.427(2) . ?
C13 H6 0.9500 . ?
C14 N4 1.343(2) . ?
C14 C15 1.489(2) . ?
C15 N1 1.358(2) . ?
C15 C16 1.411(2) . ?
C16 C17 1.390(2) . ?
C16 H7 0.9500 . ?
C17 C18 1.431(2) . ?
C17 H8 0.9500 . ?
C18 N1 1.365(2) . ?
C19 C24 1.410(3) . ?
C19 C20 1.415(2) . ?
C20 C21 1.370(2) . ?
C20 H11 0.9500 . ?
C21 C22 1.414(3) . ?
C21 H12 0.9500 . ?
C22 N5 1.360(2) . ?
C22 C23 1.414(3) . ?
C23 C24 1.371(3) . ?
C23 H13 0.9500 . ?
C24 H14 0.9500 . ?
C25 N5 1.455(2) . ?
C25 H15 0.9800 . ?
C25 H16 0.9800 . ?
C25 H17 0.9800 . ?
C26 N5 1.456(3) . ?
C26 H18 0.9800 . ?
C26 H19 0.9800 . ?
C26 H20 0.9800 . ?
C27 C28 1.400(3) . ?
C27 C32 1.401(3) . ?
C28 C29 1.390(2) . ?
C28 C34 1.512(3) . ?
C29 C30 1.391(3) . ?
C29 H9 0.9500 . ?
C30 C31 1.389(3) . ?
C30 C35 1.513(3) . ?
C31 C32 1.394(2) . ?
C31 H10 0.9500 . ?
C32 C33 1.504(3) . ?
C33 H21 0.9800 . ?
C33 H22 0.9800 . ?
C33 H23 0.9800 . ?
C34 H24 0.9800 . ?
C34 H25 0.9800 . ?
C34 H26 0.9800 . ?
C35 H27 0.9800 . ?
C35 H28 0.9800 . ?
C35 H29 0.9800 . ?
N1 Ni1 1.7799(15) . ?
N2 Ni1 1.7824(15) . ?
N3 Ni1 1.7801(15) . ?
N4 Ni1 1.7884(16) . ?

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
C2 C1 C19 119.86(16) . . ?
C2 C1 C18 122.05(16) . . ?
C19 C1 C18 118.08(16) . . ?
N2 C2 C3 105.20(15) . . ?
N2 C2 C1 120.27(15) . . ?
C3 C2 C1 134.49(16) . . ?
C4 C3 C2 108.44(15) . . ?
C4 C3 H1 125.8 . . ?
C2 C3 H1 125.8 . . ?
C3 C4 C5 106.97(15) . . ?
C3 C4 H2 126.5 . . ?
C5 C4 H2 126.5 . . ?
N2 C5 C4 107.44(15) . . ?
N2 C5 C6 110.46(14) . . ?
C4 C5 C6 142.10(15) . . ?
N3 C6 C7 107.17(15) . . ?
N3 C6 C5 109.92(14) . . ?
C7 C6 C5 142.86(15) . . ?
C8 C7 C6 107.18(15) . . ?
C8 C7 H3 126.4 . . ?
C6 C7 H3 126.4 . . ?
C7 C8 C9 107.98(15) . . ?
C7 C8 H4 126.0 . . ?
C9 C8 H4 126.0 . . ?
N3 C9 C10 120.52(15) . . ?
N3 C9 C8 105.64(15) . . ?
C10 C9 C8 133.68(17) . . ?
C11 C10 C9 123.66(16) . . ?
C11 C10 C27 119.65(16) . . ?
C9 C10 C27 116.62(16) . . ?
N4 C11 C10 120.54(16) . . ?
N4 C11 C12 105.39(15) . . ?
C10 C11 C12 133.73(16) . . ?
C13 C12 C11 108.24(15) . . ?
C13 C12 H5 125.9 . . ?
C11 C12 H5 125.9 . . ?
C12 C13 C14 107.04(14) . . ?
C12 C13 H6 126.5 . . ?
C14 C13 H6 126.5 . . ?
N4 C14 C13 107.74(15) . . ?
N4 C14 C15 110.41(14) . . ?
C13 C14 C15 141.56(15) . . ?
N1 C15 C16 107.65(15) . . ?
N1 C15 C14 110.03(14) . . ?
C16 C15 C14 142.14(15) . . ?
C17 C16 C15 106.71(15) . . ?
C17 C16 H7 126.6 . . ?
C15 C16 H7 126.6 . . ?
C16 C17 C18 108.63(15) . . ?
C16 C17 H8 125.7 . . ?
C18 C17 H8 125.7 . . ?
N1 C18 C17 105.28(15) . . ?
N1 C18 C1 120.82(15) . . ?
C17 C18 C1 133.50(16) . . ?
C24 C19 C20 116.04(16) . . ?
C24 C19 C1 122.88(16) . . ?
C20 C19 C1 121.04(16) . . ?
C21 C20 C19 122.39(16) . . ?
C21 C20 H11 118.8 . . ?
C19 C20 H11 118.8 . . ?
C20 C21 C22 120.91(16) . . ?
C20 C21 H12 119.5 . . ?
C22 C21 H12 119.5 . . ?
N5 C22 C23 120.89(17) . . ?
N5 C22 C21 121.87(16) . . ?
C23 C22 C21 117.23(16) . . ?
C24 C23 C22 121.07(17) . . ?
C24 C23 H13 119.5 . . ?
C22 C23 H13 119.5 . . ?
C23 C24 C19 122.34(16) . . ?
C23 C24 H14 118.8 . . ?
C19 C24 H14 118.8 . . ?
N5 C25 H15 109.5 . . ?
N5 C25 H16 109.5 . . ?
H15 C25 H16 109.5 . . ?
N5 C25 H17 109.5 . . ?
H15 C25 H17 109.5 . . ?
H16 C25 H17 109.5 . . ?
N5 C26 H18 109.5 . . ?
N5 C26 H19 109.5 . . ?
H18 C26 H19 109.5 . . ?
N5 C26 H20 109.5 . . ?
H18 C26 H20 109.5 . . ?
H19 C26 H20 109.5 . . ?
C28 C27 C32 120.67(17) . . ?
C28 C27 C10 119.97(16) . . ?
C32 C27 C10 119.34(15) . . ?
C29 C28 C27 118.58(17) . . ?
C29 C28 C34 120.40(16) . . ?
C27 C28 C34 121.02(16) . . ?
C28 C29 C30 121.99(17) . . ?
C28 C29 H9 119.0 . . ?
C30 C29 H9 119.0 . . ?
C31 C30 C29 118.31(17) . . ?
C31 C30 C35 120.90(18) . . ?
C29 C30 C35 120.80(17) . . ?
C30 C31 C32 121.67(17) . . ?
C30 C31 H10 119.2 . . ?
C32 C31 H10 119.2 . . ?
C31 C32 C27 118.77(16) . . ?
C31 C32 C33 120.01(16) . . ?
C27 C32 C33 121.22(16) . . ?
C32 C33 H21 109.5 . . ?
C32 C33 H22 109.5 . . ?
H21 C33 H22 109.5 . . ?
C32 C33 H23 109.5 . . ?
H21 C33 H23 109.5 . . ?
H22 C33 H23 109.5 . . ?
C28 C34 H24 109.5 . . ?
C28 C34 H25 109.5 . . ?
H24 C34 H25 109.5 . . ?
C28 C34 H26 109.5 . . ?
H24 C34 H26 109.5 . . ?
H25 C34 H26 109.5 . . ?
C30 C35 H27 109.5 . . ?
C30 C35 H28 109.5 . . ?
H27 C35 H28 109.5 . . ?
C30 C35 H29 109.5 . . ?
H27 C35 H29 109.5 . . ?
H28 C35 H29 109.5 . . ?
C15 N1 C18 111.71(14) . . ?
C15 N1 Ni1 116.51(12) . . ?
C18 N1 Ni1 130.70(12) . . ?
C5 N2 C2 111.93(14) . . ?
C5 N2 Ni1 116.70(12) . . ?
C2 N2 Ni1 131.26(12) . . ?
C6 N3 C9 112.02(14) . . ?
C6 N3 Ni1 117.44(12) . . ?
C9 N3 Ni1 130.53(12) . . ?
C14 N4 C11 111.54(15) . . ?
C14 N4 Ni1 116.53(12) . . ?
C11 N4 Ni1 129.81(12) . . ?
C22 N5 C25 120.87(16) . . ?
C22 N5 C26 120.88(16) . . ?
C25 N5 C26 117.74(15) . . ?
N1 Ni1 N3 178.03(6) . . ?
N1 Ni1 N2 94.57(7) . . ?
N3 Ni1 N2 85.38(7) . . ?
N1 Ni1 N4 85.52(7) . . ?
N3 Ni1 N4 94.38(7) . . ?
N2 Ni1 N4 175.72(6) . . ?

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
C19 C1 C2 N2 175.97(15) . . . . ?
C18 C1 C2 N2 -3.3(2) . . . . ?
C19 C1 C2 C3 -1.3(3) . . . . ?
C18 C1 C2 C3 179.44(18) . . . . ?
N2 C2 C3 C4 1.0(2) . . . . ?
C1 C2 C3 C4 178.53(18) . . . . ?
C2 C3 C4 C5 -1.4(2) . . . . ?
C3 C4 C5 N2 1.3(2) . . . . ?
C3 C4 C5 C6 -178.0(2) . . . . ?
N2 C5 C6 N3 0.0(2) . . . . ?
C4 C5 C6 N3 179.3(2) . . . . ?
N2 C5 C6 C7 176.9(2) . . . . ?
C4 C5 C6 C7 -3.8(4) . . . . ?
N3 C6 C7 C8 0.7(2) . . . . ?
C5 C6 C7 C8 -176.3(2) . . . . ?
C6 C7 C8 C9 0.1(2) . . . . ?
C7 C8 C9 N3 -0.9(2) . . . . ?
C7 C8 C9 C10 174.35(19) . . . . ?
N3 C9 C10 C11 -2.4(3) . . . . ?
C8 C9 C10 C11 -177.02(18) . . . . ?
N3 C9 C10 C27 174.51(15) . . . . ?
C8 C9 C10 C27 -0.1(3) . . . . ?
C9 C10 C11 N4 -4.1(3) . . . . ?
C27 C10 C11 N4 179.11(15) . . . . ?
C9 C10 C11 C12 168.22(18) . . . . ?
C27 C10 C11 C12 -8.6(3) . . . . ?
N4 C11 C12 C13 1.90(19) . . . . ?
C10 C11 C12 C13 -171.23(18) . . . . ?
C11 C12 C13 C14 -0.87(19) . . . . ?
C12 C13 C14 N4 -0.53(19) . . . . ?
C12 C13 C14 C15 172.3(2) . . . . ?
N4 C14 C15 N1 1.74(19) . . . . ?
C13 C14 C15 N1 -171.0(2) . . . . ?
N4 C14 C15 C16 176.0(2) . . . . ?
C13 C14 C15 C16 3.3(4) . . . . ?
N1 C15 C16 C17 0.77(19) . . . . ?
C14 C15 C16 C17 -173.5(2) . . . . ?
C15 C16 C17 C18 -0.04(19) . . . . ?
C16 C17 C18 N1 -0.69(18) . . . . ?
C16 C17 C18 C1 171.80(17) . . . . ?
C2 C1 C18 N1 6.6(2) . . . . ?
C19 C1 C18 N1 -172.62(14) . . . . ?
C2 C1 C18 C17 -164.93(17) . . . . ?
C19 C1 C18 C17 15.8(3) . . . . ?
C2 C1 C19 C24 34.2(2) . . . . ?
C18 C1 C19 C24 -146.56(16) . . . . ?
C2 C1 C19 C20 -143.51(16) . . . . ?
C18 C1 C19 C20 35.7(2) . . . . ?
C24 C19 C20 C21 -0.4(2) . . . . ?
C1 C19 C20 C21 177.41(16) . . . . ?
C19 C20 C21 C22 1.4(3) . . . . ?
C20 C21 C22 N5 179.28(17) . . . . ?
C20 C21 C22 C23 -1.2(2) . . . . ?
N5 C22 C23 C24 179.61(16) . . . . ?
C21 C22 C23 C24 0.1(2) . . . . ?
C22 C23 C24 C19 0.9(3) . . . . ?
C20 C19 C24 C23 -0.7(2) . . . . ?
C1 C19 C24 C23 -178.50(15) . . . . ?
C11 C10 C27 C28 -81.8(2) . . . . ?
C9 C10 C27 C28 101.14(19) . . . . ?
C11 C10 C27 C32 99.8(2) . . . . ?
C9 C10 C27 C32 -77.2(2) . . . . ?
C32 C27 C28 C29 1.1(3) . . . . ?
C10 C27 C28 C29 -177.18(16) . . . . ?
C32 C27 C28 C34 -179.06(16) . . . . ?
C10 C27 C28 C34 2.6(3) . . . . ?
C27 C28 C29 C30 0.0(3) . . . . ?
C34 C28 C29 C30 -179.87(17) . . . . ?
C28 C29 C30 C31 -0.6(3) . . . . ?
C28 C29 C30 C35 179.27(17) . . . . ?
C29 C30 C31 C32 0.2(3) . . . . ?
C35 C30 C31 C32 -179.68(17) . . . . ?
C30 C31 C32 C27 0.8(3) . . . . ?
C30 C31 C32 C33 -178.36(17) . . . . ?
C28 C27 C32 C31 -1.5(3) . . . . ?
C10 C27 C32 C31 176.80(16) . . . . ?
C28 C27 C32 C33 177.69(17) . . . . ?
C10 C27 C32 C33 -4.0(3) . . . . ?
C16 C15 N1 C18 -1.27(19) . . . . ?
C14 C15 N1 C18 175.01(13) . . . . ?
C16 C15 N1 Ni1 -170.71(11) . . . . ?
C14 C15 N1 Ni1 5.57(17) . . . . ?
C17 C18 N1 C15 1.21(18) . . . . ?
C1 C18 N1 C15 -172.45(14) . . . . ?
C17 C18 N1 Ni1 168.72(12) . . . . ?
C1 C18 N1 Ni1 -4.9(2) . . . . ?
C4 C5 N2 C2 -0.7(2) . . . . ?
C6 C5 N2 C2 178.82(14) . . . . ?
C4 C5 N2 Ni1 -177.32(12) . . . . ?
C6 C5 N2 Ni1 2.24(18) . . . . ?
C3 C2 N2 C5 -0.12(19) . . . . ?
C1 C2 N2 C5 -178.12(15) . . . . ?
C3 C2 N2 Ni1 175.82(13) . . . . ?
C1 C2 N2 Ni1 -2.2(2) . . . . ?
C7 C6 N3 C9 -1.3(2) . . . . ?
C5 C6 N3 C9 176.77(14) . . . . ?
C7 C6 N3 Ni1 179.73(11) . . . . ?
C5 C6 N3 Ni1 -2.25(18) . . . . ?
C10 C9 N3 C6 -174.66(15) . . . . ?
C8 C9 N3 C6 1.3(2) . . . . ?
C10 C9 N3 Ni1 4.2(3) . . . . ?
C8 C9 N3 Ni1 -179.83(13) . . . . ?
C13 C14 N4 C11 1.81(19) . . . . ?
C15 C14 N4 C11 -173.43(13) . . . . ?
C13 C14 N4 Ni1 166.89(11) . . . . ?
C15 C14 N4 Ni1 -8.35(17) . . . . ?
C10 C11 N4 C14 171.94(15) . . . . ?
C12 C11 N4 C14 -2.30(18) . . . . ?
C10 C11 N4 Ni1 9.4(2) . . . . ?
C12 C11 N4 Ni1 -164.85(12) . . . . ?
C23 C22 N5 C25 171.93(17) . . . . ?
C21 C22 N5 C25 -8.6(3) . . . . ?
C23 C22 N5 C26 0.3(3) . . . . ?
C21 C22 N5 C26 179.82(16) . . . . ?
C15 N1 Ni1 N2 167.37(12) . . . . ?
C18 N1 Ni1 N2 0.35(15) . . . . ?
C15 N1 Ni1 N4 -8.33(12) . . . . ?
C18 N1 Ni1 N4 -175.35(15) . . . . ?
C6 N3 Ni1 N2 2.88(13) . . . . ?
C9 N3 Ni1 N2 -175.92(16) . . . . ?
C6 N3 Ni1 N4 178.59(13) . . . . ?
C9 N3 Ni1 N4 -0.21(16) . . . . ?
C5 N2 Ni1 N1 179.13(13) . . . . ?
C2 N2 Ni1 N1 3.34(16) . . . . ?
C5 N2 Ni1 N3 -2.85(13) . . . . ?
C2 N2 Ni1 N3 -178.63(16) . . . . ?
C14 N4 Ni1 N1 9.48(13) . . . . ?
C11 N4 Ni1 N1 171.31(15) . . . . ?
C14 N4 Ni1 N3 -168.55(13) . . . . ?
C11 N4 Ni1 N3 -6.72(16) . . . . ?

_refine_diff_density_max         0.403
_refine_diff_density_min         -0.298
_refine_diff_density_rms         0.077

_shelxl_version_number           2014-3



####################################################################### 
# 
# 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_shelxl
_database_code_depnum_ccdc_archive 'CCDC 1511826'
_audit_update_record             
;
2016-10-27 deposited with the CCDC.
2016-12-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C51 H31.50 F9 N7.50 Ni1.50'
_chemical_formula_weight         1008.40

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
Ni Ni 0.3393 1.1124 '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'
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'
F F 0.0171 0.0103 '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                   17.128(4)
_cell_length_b                   11.539(2)
_cell_length_c                   21.492(4)
_cell_angle_alpha                90
_cell_angle_beta                 94.759(3)
_cell_angle_gamma                90
_cell_volume                     4233.1(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    113(2)
_cell_measurement_reflns_used    13481
_cell_measurement_theta_min      1.90
_cell_measurement_theta_max      31.56

_exptl_crystal_description       prism
_exptl_crystal_colour            black
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.582
_exptl_crystal_F_000             2052
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.763
_shelx_estimated_absorpt_T_min   0.862
_shelx_estimated_absorpt_T_max   0.862
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.692
_exptl_absorpt_correction_T_max  0.859
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      113(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Rigaku Saturn724'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 14.222
_diffrn_reflns_number            12520
_diffrn_reflns_av_unetI/netI     0.0457
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         1.902
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.968
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.968
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.968
_reflns_number_total             7421
_reflns_number_gt                6445
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Data were apparently pre-merged, so _diffrn_reflns_number
 etc. will have to be added later.
 
 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       'CrystalClear (Rigaku Inc., 2008)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_computing_structure_solution    'SIR97 (Altomare, et al., 1999)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0916P)²+6.1889P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7421
_refine_ls_number_parameters     677
_refine_ls_number_restraints     60
_refine_ls_R_factor_all          0.0784
_refine_ls_R_factor_gt           0.0695
_refine_ls_wR_factor_ref         0.1885
_refine_ls_wR_factor_gt          0.1807
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_restrained_S_all      1.082
_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
C1 C 0.9355(3) 0.2036(4) 1.02616(18) 0.0451(9) Uani 1 1 d . . . . .
C2 C 0.8626(3) 0.2604(4) 1.0355(2) 0.0513(10) Uani 1 1 d . . . . .
H1 H 0.8550 0.3409 1.0420 0.062 Uiso 1 1 calc R U . . .
C3 C 0.8060(3) 0.1758(4) 1.0330(2) 0.0512(10) Uani 1 1 d . . . . .
H2 H 0.7518 0.1880 1.0372 0.061 Uiso 1 1 calc R U . . .
C4 C 0.8428(3) 0.0639(4) 1.0230(2) 0.0459(10) Uani 1 1 d . . . . .
C5 C 0.8145(3) -0.0524(4) 1.01600(19) 0.0451(9) Uani 1 1 d . . . . .
C6 C 0.8657(3) -0.1486(4) 1.00152(19) 0.0474(10) Uani 1 1 d . . . . .
C7 C 0.8556(3) -0.2715(4) 0.9963(2) 0.0512(10) Uani 1 1 d . . . . .
H3 H 0.8084 -0.3126 1.0009 0.061 Uiso 1 1 calc R U . . .
C8 C 0.9266(3) -0.3205(4) 0.98335(19) 0.0483(10) Uani 1 1 d . . . . .
H4 H 0.9366 -0.4005 0.9772 0.058 Uiso 1 1 calc R U . . .
C9 C 0.9814(3) -0.2284(4) 0.98102(19) 0.0468(10) Uani 1 1 d . . . . .
C10 C 0.7319(3) -0.0757(4) 1.02426(19) 0.0474(10) Uani 1 1 d . . . . .
C11 C 0.6923(3) -0.0202(4) 1.0712(2) 0.0513(10) Uani 1 1 d . . . . .
H5 H 0.7194 0.0359 1.0971 0.062 Uiso 1 1 calc R U . . .
C12 C 0.6161(3) -0.0451(4) 1.0803(3) 0.0606(12) Uani 1 1 d . . . . .
H6 H 0.5912 -0.0050 1.1118 0.073 Uiso 0.5 1 calc R U P A 1
C13 C 0.5741(3) -0.1287(5) 1.0440(3) 0.0720(15) Uani 1 1 d . . . . .
H7 H 0.5210 -0.1457 1.0502 0.086 Uiso 0.5 1 calc R U P B 2
C14 C 0.6127(3) -0.1855(5) 0.9989(3) 0.0690(14) Uani 1 1 d . . . . .
H8 H 0.5861 -0.2448 0.9748 0.083 Uiso 0.5 1 calc R U P C 1
C15 C 0.6890(3) -0.1580(4) 0.9879(2) 0.0566(11) Uani 1 1 d . . . . .
H9 H 0.7127 -0.1958 0.9551 0.068 Uiso 1 1 calc R U . . .
C16 C 0.5759(7) 0.0160(10) 1.1346(6) 0.068(3) Uani 0.5 1 d . U P D 2
C17 C 0.4571(8) -0.0885(14) 1.0855(9) 0.112(5) Uani 0.5 1 d . U P E 1
H10 H 0.4717 -0.1132 1.1285 0.168 Uiso 0.5 1 calc R U P E 1
H11 H 0.4011 -0.1022 1.0753 0.168 Uiso 0.5 1 calc R U P E 1
H12 H 0.4685 -0.0058 1.0813 0.168 Uiso 0.5 1 calc R U P E 1
C18 C 0.4647(7) -0.2544(16) 1.0165(8) 0.102(5) Uani 0.5 1 d . U P E 1
H13 H 0.4694 -0.2525 0.9714 0.152 Uiso 0.5 1 calc R U P E 1
H14 H 0.4092 -0.2572 1.0245 0.152 Uiso 0.5 1 calc R U P E 1
H15 H 0.4914 -0.3232 1.0345 0.152 Uiso 0.5 1 calc R U P E 1
C19 C 0.5631(8) -0.2847(15) 0.9674(6) 0.092(4) Uani 0.5 1 d . U P F 2
C20 C 0.8278(3) 0.1670(4) 0.8758(2) 0.0473(10) Uani 1 1 d . . . . .
C21 C 0.7465(3) 0.1548(4) 0.8788(2) 0.0505(10) Uani 1 1 d . . . . .
H16 H 0.7107 0.2151 0.8863 0.061 Uiso 1 1 calc R U . . .
C22 C 0.7279(3) 0.0384(4) 0.8687(2) 0.0504(10) Uani 1 1 d . . . . .
H17 H 0.6772 0.0050 0.8682 0.061 Uiso 1 1 calc R U . . .
C23 C 0.7987(3) -0.0216(4) 0.8593(2) 0.0462(10) Uani 1 1 d . . . . .
C24 C 0.8167(3) -0.1403(4) 0.84306(19) 0.0455(9) Uani 1 1 d . . . . .
C25 C 0.8934(3) -0.1806(4) 0.83606(19) 0.0453(9) Uani 1 1 d . . . . .
C26 C 0.9246(3) -0.2869(4) 0.81271(19) 0.0489(10) Uani 1 1 d . . . . .
H18 H 0.8963 -0.3568 0.8045 0.059 Uiso 1 1 calc R U . . .
C27 C 1.0027(3) -0.2689(4) 0.8045(2) 0.0496(10) Uani 1 1 d . . . . .
H19 H 1.0377 -0.3236 0.7889 0.060 Uiso 1 1 calc R U . . .
C28 C 1.0212(3) -0.1520(4) 0.82385(19) 0.0482(10) Uani 1 1 d . . . . .
C29 C 1.0846(3) -0.0641(4) 0.82218(19) 0.0470(10) Uani 1 1 d . . . . .
C30 C 1.1574(3) -0.0462(4) 0.7990(2) 0.0533(11) Uani 1 1 d . . . . .
H20 H 1.1882 -0.1030 0.7805 0.064 Uiso 1 1 calc R U . . .
C31 C 1.1769(3) 0.0715(4) 0.8080(2) 0.0519(11) Uani 1 1 d . . . . .
H21 H 1.2234 0.1085 0.7971 0.062 Uiso 1 1 calc R U . . .
C32 C 1.1139(2) 0.1247(4) 0.83637(19) 0.0451(9) Uani 1 1 d . . . . .
C33 C 1.0945(2) 0.2457(4) 0.84743(19) 0.0437(9) Uani 1 1 d . . . . .
C34 C 1.0196(2) 0.2805(4) 0.86155(19) 0.0443(9) Uani 1 1 d . . . . .
C35 C 0.9848(3) 0.3929(4) 0.8745(2) 0.0482(10) Uani 1 1 d . . . . .
H22 H 1.0113 0.4653 0.8767 0.058 Uiso 1 1 calc R U . . .
C36 C 0.9066(3) 0.3747(4) 0.8829(2) 0.0499(10) Uani 1 1 d . . . . .
H23 H 0.8695 0.4326 0.8914 0.060 Uiso 1 1 calc R U . . .
C37 C 0.8916(2) 0.2538(4) 0.8766(2) 0.0462(10) Uani 1 1 d . . . . .
C38 C 0.7486(3) -0.2187(4) 0.82725(19) 0.0457(9) Uani 1 1 d . . . . .
C39 C 0.6842(3) -0.1784(4) 0.7891(2) 0.0508(10) Uani 1 1 d . . . . .
H24 H 0.6852 -0.1028 0.7717 0.061 Uiso 1 1 calc R U . . .
C40 C 0.6184(3) -0.2486(4) 0.7764(2) 0.0579(12) Uani 1 1 d . . . . .
C41 C 0.6169(3) -0.3596(4) 0.7994(3) 0.0660(14) Uani 1 1 d . . . . .
H25 H 0.5724 -0.4077 0.7900 0.079 Uiso 1 1 calc R U . . .
C42 C 0.6816(3) -0.4006(4) 0.8366(3) 0.0617(12) Uani 1 1 d . . . . .
C43 C 0.7469(3) -0.3314(4) 0.8505(2) 0.0511(10) Uani 1 1 d . . . . .
H26 H 0.7905 -0.3608 0.8759 0.061 Uiso 1 1 calc R U . . .
C44 C 0.5497(3) -0.2022(5) 0.7359(3) 0.0715(15) Uani 1 1 d . . . . .
C45 C 0.6803(4) -0.5227(6) 0.8584(4) 0.0827(18) Uani 1 1 d . . . . .
C46 C 1.1545(2) 0.3341(4) 0.84016(19) 0.0454(9) Uani 1 1 d . . . . .
C47 C 1.2311(3) 0.3202(4) 0.8674(2) 0.0494(10) Uani 1 1 d . . . . .
H27 H 1.2453 0.2494 0.8879 0.059 Uiso 1 1 calc R U . . .
C48 C 1.2868(3) 0.4067(4) 0.8652(2) 0.0538(11) Uani 1 1 d . . . . .
H28 H 1.3374 0.3963 0.8861 0.065 Uiso 1 1 calc R U . . .
C49 C 1.2689(3) 0.5099(4) 0.8323(2) 0.0520(11) Uani 1 1 d . . . . .
C50 C 1.1930(3) 0.5224(4) 0.8027(2) 0.0516(11) Uani 1 1 d . . . . .
H29 H 1.1800 0.5907 0.7794 0.062 Uiso 1 1 calc R U . . .
C51 C 1.1372(3) 0.4370(4) 0.8070(2) 0.0471(10) Uani 1 1 d . . . . .
H30 H 1.0861 0.4481 0.7871 0.057 Uiso 1 1 calc R U . . .
C52 C 1.3957(3) 0.5912(6) 0.8699(3) 0.0873(19) Uani 1 1 d . . . . .
H31 H 1.3809 0.5949 0.9129 0.131 Uiso 1 1 calc R U . . .
H32 H 1.4291 0.6577 0.8619 0.131 Uiso 1 1 calc R U . . .
H33 H 1.4244 0.5192 0.8639 0.131 Uiso 1 1 calc R U . . .
C53 C 1.3013(3) 0.7066(5) 0.8018(3) 0.0786(16) Uani 1 1 d . . . . .
H34 H 1.2746 0.6966 0.7600 0.118 Uiso 1 1 calc R U . . .
H35 H 1.3474 0.7560 0.7992 0.118 Uiso 1 1 calc R U . . .
H36 H 1.2654 0.7429 0.8292 0.118 Uiso 1 1 calc R U . . .
N1 N 0.9207(2) 0.0893(3) 1.01928(16) 0.0466(8) Uani 1 1 d . . . . .
N2 N 0.9421(2) -0.1280(3) 0.99144(16) 0.0453(8) Uani 1 1 d . . . . .
N3 N 0.5001(5) -0.1518(10) 1.0448(6) 0.089(3) Uani 0.5 1 d . U P E 1
N4 N 0.8569(2) 0.0592(3) 0.86519(17) 0.0471(8) Uani 1 1 d . . . . .
N5 N 0.9566(2) -0.1045(3) 0.84422(17) 0.0470(8) Uani 1 1 d . . . . .
N6 N 1.0605(2) 0.0394(3) 0.84425(16) 0.0447(8) Uani 1 1 d . . . . .
N7 N 0.9598(2) 0.2016(3) 0.86510(16) 0.0460(8) Uani 1 1 d . . . . .
N8 N 1.3256(2) 0.5942(4) 0.8269(2) 0.0694(12) Uani 1 1 d . . . . .
Ni1 Ni 1.0000 0.0000 1.0000 0.0451(2) Uani 1 2 d S . P . .
Ni2 Ni 0.95968(3) 0.04756(5) 0.85929(3) 0.0457(2) Uani 1 1 d . . . . .
F1 F 0.6211(4) 0.0230(6) 1.1892(3) 0.0845(19) Uani 0.5 1 d . U P D 2
F2 F 0.5597(5) 0.1272(6) 1.1198(4) 0.095(2) Uani 0.5 1 d . U P D 2
F3 F 0.5083(5) -0.0309(8) 1.1493(5) 0.123(3) Uani 0.5 1 d . U P D 2
F4 F 0.4960(5) -0.3115(10) 0.9889(4) 0.116(3) Uani 0.5 1 d . U P F 2
F5 F 0.5506(5) -0.2570(10) 0.9086(4) 0.134(4) Uani 0.5 1 d . U P F 2
F6 F 0.6064(6) -0.3851(10) 0.9680(5) 0.140(4) Uani 0.5 1 d . U P F 2
F7 F 0.55565(19) -0.2188(4) 0.67495(18) 0.0912(11) Uani 1 1 d . . . . .
F8 F 0.5396(2) -0.0894(4) 0.7431(2) 0.1210(16) Uani 1 1 d . . . . .
F9 F 0.48258(18) -0.2547(4) 0.74777(19) 0.1001(12) Uani 1 1 d . . . . .
F10 F 0.7226(2) -0.5385(3) 0.91342(18) 0.0852(10) Uani 1 1 d . . . . .
F11 F 0.6110(2) -0.5661(4) 0.8632(3) 0.1287(18) Uani 1 1 d . . . . .
F12 F 0.7138(3) -0.5965(3) 0.8185(2) 0.1277(17) Uani 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
C1 N1 1.348(6) . ?
C1 C2 1.439(6) . ?
C1 C9 1.473(6) 3_757 ?
C2 C3 1.374(7) . ?
C2 H1 0.9500 . ?
C3 C4 1.460(6) . ?
C3 H2 0.9500 . ?
C4 N1 1.374(6) . ?
C4 C5 1.430(6) . ?
C5 C6 1.464(6) . ?
C5 C10 1.466(6) . ?
C6 N2 1.365(6) . ?
C6 C7 1.432(6) . ?
C7 C8 1.390(6) . ?
C7 H3 0.9500 . ?
C8 C9 1.421(6) . ?
C8 H4 0.9500 . ?
C9 N2 1.368(5) . ?
C9 C1 1.473(6) 3_757 ?
C10 C15 1.399(6) . ?
C10 C11 1.414(7) . ?
C11 C12 1.366(7) . ?
C11 H5 0.9500 . ?
C12 C13 1.402(8) . ?
C12 C16 1.570(12) . ?
C12 H6 0.9500 . ?
C13 N3 1.297(10) . ?
C13 C14 1.384(8) . ?
C13 H7 0.9500 . ?
C14 C15 1.385(7) . ?
C14 C19 1.547(14) . ?
C14 H8 0.9500 . ?
C15 H9 0.9500 . ?
C16 F3 1.341(13) . ?
C16 F2 1.345(13) . ?
C16 F1 1.354(14) . ?
C17 N3 1.395(18) . ?
C17 H10 0.9800 . ?
C17 H11 0.9800 . ?
C17 H12 0.9800 . ?
C18 N3 1.440(19) . ?
C18 H13 0.9800 . ?
C18 H14 0.9800 . ?
C18 H15 0.9800 . ?
C19 F5 1.306(17) . ?
C19 F4 1.310(14) . ?
C19 F6 1.374(19) . ?
C20 N4 1.366(5) . ?
C20 C21 1.406(6) . ?
C20 C37 1.482(6) . ?
C21 C22 1.394(6) . ?
C21 H16 0.9500 . ?
C22 C23 1.424(6) . ?
C22 H17 0.9500 . ?
C23 N4 1.364(5) . ?
C23 C24 1.452(6) . ?
C24 C25 1.413(6) . ?
C24 C38 1.493(6) . ?
C25 N5 1.394(5) . ?
C25 C26 1.444(6) . ?
C26 C27 1.379(6) . ?
C26 H18 0.9500 . ?
C27 C28 1.440(6) . ?
C27 H19 0.9500 . ?
C28 N5 1.339(6) . ?
C28 C29 1.489(6) . ?
C29 N6 1.362(5) . ?
C29 C30 1.396(7) . ?
C30 C31 1.408(7) . ?
C30 H20 0.9500 . ?
C31 C32 1.421(6) . ?
C31 H21 0.9500 . ?
C32 N6 1.364(6) . ?
C32 C33 1.460(6) . ?
C33 C34 1.402(6) . ?
C33 C46 1.466(6) . ?
C34 N7 1.376(5) . ?
C34 C35 1.463(6) . ?
C35 C36 1.383(6) . ?
C35 H22 0.9500 . ?
C36 C37 1.423(6) . ?
C36 H23 0.9500 . ?
C37 N7 1.355(5) . ?
C38 C43 1.395(6) . ?
C38 C39 1.398(6) . ?
C39 C40 1.395(6) . ?
C39 H24 0.9500 . ?
C40 C41 1.373(7) . ?
C40 C44 1.504(7) . ?
C41 C42 1.394(7) . ?
C41 H25 0.9500 . ?
C42 C43 1.387(7) . ?
C42 C45 1.486(8) . ?
C43 H26 0.9500 . ?
C44 F8 1.323(7) . ?
C44 F7 1.336(7) . ?
C44 F9 1.343(6) . ?
C45 F11 1.299(7) . ?
C45 F10 1.348(7) . ?
C45 F12 1.368(8) . ?
C46 C47 1.401(6) . ?
C46 C51 1.405(6) . ?
C47 C48 1.384(6) . ?
C47 H27 0.9500 . ?
C48 C49 1.405(7) . ?
C48 H28 0.9500 . ?
C49 N8 1.385(6) . ?
C49 C50 1.407(7) . ?
C50 C51 1.382(6) . ?
C50 H29 0.9500 . ?
C51 H30 0.9500 . ?
C52 N8 1.454(7) . ?
C52 H31 0.9800 . ?
C52 H32 0.9800 . ?
C52 H33 0.9800 . ?
C53 N8 1.452(7) . ?
C53 H34 0.9800 . ?
C53 H35 0.9800 . ?
C53 H36 0.9800 . ?
N1 Ni1 1.781(4) . ?
N2 Ni1 1.780(4) . ?
N4 Ni2 1.780(4) . ?
N5 Ni2 1.785(4) . ?
N6 Ni2 1.785(4) . ?
N7 Ni2 1.782(4) . ?
Ni1 N2 1.780(4) 3_757 ?
Ni1 N1 1.781(4) 3_757 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 C2 107.6(4) . . ?
N1 C1 C9 110.7(4) . 3_757 ?
C2 C1 C9 141.6(4) . 3_757 ?
C3 C2 C1 106.7(4) . . ?
C3 C2 H1 126.6 . . ?
C1 C2 H1 126.6 . . ?
C2 C3 C4 108.8(4) . . ?
C2 C3 H2 125.6 . . ?
C4 C3 H2 125.6 . . ?
N1 C4 C5 121.1(4) . . ?
N1 C4 C3 104.6(4) . . ?
C5 C4 C3 134.3(4) . . ?
C4 C5 C6 122.0(4) . . ?
C4 C5 C10 118.8(4) . . ?
C6 C5 C10 119.2(4) . . ?
N2 C6 C7 105.8(4) . . ?
N2 C6 C5 120.0(4) . . ?
C7 C6 C5 134.2(4) . . ?
C8 C7 C6 108.5(4) . . ?
C8 C7 H3 125.8 . . ?
C6 C7 H3 125.8 . . ?
C7 C8 C9 107.1(4) . . ?
C7 C8 H4 126.5 . . ?
C9 C8 H4 126.5 . . ?
N2 C9 C8 107.0(4) . . ?
N2 C9 C1 110.2(4) . 3_757 ?
C8 C9 C1 142.7(4) . 3_757 ?
C15 C10 C11 116.4(4) . . ?
C15 C10 C5 121.6(4) . . ?
C11 C10 C5 121.9(4) . . ?
C12 C11 C10 121.9(5) . . ?
C12 C11 H5 119.1 . . ?
C10 C11 H5 119.1 . . ?
C11 C12 C13 121.2(5) . . ?
C11 C12 C16 119.7(6) . . ?
C13 C12 C16 119.1(6) . . ?
C11 C12 H6 119.4 . . ?
C13 C12 H6 119.4 . . ?
N3 C13 C14 115.8(8) . . ?
N3 C13 C12 126.3(8) . . ?
C14 C13 C12 117.6(5) . . ?
C14 C13 H7 121.2 . . ?
C12 C13 H7 121.2 . . ?
C13 C14 C15 121.6(5) . . ?
C13 C14 C19 112.4(7) . . ?
C15 C14 C19 125.9(7) . . ?
C13 C14 H8 119.2 . . ?
C15 C14 H8 119.2 . . ?
C14 C15 C10 121.4(5) . . ?
C14 C15 H9 119.3 . . ?
C10 C15 H9 119.3 . . ?
F3 C16 F2 106.0(10) . . ?
F3 C16 F1 105.2(10) . . ?
F2 C16 F1 103.9(9) . . ?
F3 C16 C12 115.8(9) . . ?
F2 C16 C12 110.4(9) . . ?
F1 C16 C12 114.7(9) . . ?
N3 C17 H10 109.5 . . ?
N3 C17 H11 109.5 . . ?
H10 C17 H11 109.5 . . ?
N3 C17 H12 109.5 . . ?
H10 C17 H12 109.5 . . ?
H11 C17 H12 109.5 . . ?
N3 C18 H13 109.5 . . ?
N3 C18 H14 109.5 . . ?
H13 C18 H14 109.5 . . ?
N3 C18 H15 109.5 . . ?
H13 C18 H15 109.5 . . ?
H14 C18 H15 109.5 . . ?
F5 C19 F4 108.7(11) . . ?
F5 C19 F6 105.0(12) . . ?
F4 C19 F6 106.6(14) . . ?
F5 C19 C14 106.4(11) . . ?
F4 C19 C14 119.1(11) . . ?
F6 C19 C14 110.2(10) . . ?
N4 C20 C21 107.1(4) . . ?
N4 C20 C37 109.7(4) . . ?
C21 C20 C37 143.1(4) . . ?
C22 C21 C20 107.7(4) . . ?
C22 C21 H16 126.2 . . ?
C20 C21 H16 126.2 . . ?
C21 C22 C23 107.7(4) . . ?
C21 C22 H17 126.1 . . ?
C23 C22 H17 126.1 . . ?
N4 C23 C22 106.2(4) . . ?
N4 C23 C24 119.9(4) . . ?
C22 C23 C24 133.9(4) . . ?
C25 C24 C23 123.6(4) . . ?
C25 C24 C38 119.5(4) . . ?
C23 C24 C38 116.6(4) . . ?
N5 C25 C24 119.9(4) . . ?
N5 C25 C26 105.8(4) . . ?
C24 C25 C26 133.7(4) . . ?
C27 C26 C25 107.9(4) . . ?
C27 C26 H18 126.0 . . ?
C25 C26 H18 126.0 . . ?
C26 C27 C28 107.2(4) . . ?
C26 C27 H19 126.4 . . ?
C28 C27 H19 126.4 . . ?
N5 C28 C27 108.1(4) . . ?
N5 C28 C29 110.7(4) . . ?
C27 C28 C29 140.8(4) . . ?
N6 C29 C30 107.4(4) . . ?
N6 C29 C28 110.2(4) . . ?
C30 C29 C28 141.7(4) . . ?
C29 C30 C31 107.6(4) . . ?
C29 C30 H20 126.2 . . ?
C31 C30 H20 126.2 . . ?
C30 C31 C32 107.2(4) . . ?
C30 C31 H21 126.4 . . ?
C32 C31 H21 126.4 . . ?
N6 C32 C31 106.4(4) . . ?
N6 C32 C33 120.4(4) . . ?
C31 C32 C33 132.4(4) . . ?
C34 C33 C32 122.3(4) . . ?
C34 C33 C46 119.1(4) . . ?
C32 C33 C46 118.5(4) . . ?
N7 C34 C33 121.4(4) . . ?
N7 C34 C35 105.1(4) . . ?
C33 C34 C35 133.6(4) . . ?
C36 C35 C34 107.7(4) . . ?
C36 C35 H22 126.2 . . ?
C34 C35 H22 126.2 . . ?
C35 C36 C37 107.8(4) . . ?
C35 C36 H23 126.1 . . ?
C37 C36 H23 126.1 . . ?
N7 C37 C36 107.6(4) . . ?
N7 C37 C20 110.1(4) . . ?
C36 C37 C20 142.3(4) . . ?
C43 C38 C39 118.8(4) . . ?
C43 C38 C24 121.5(4) . . ?
C39 C38 C24 119.7(4) . . ?
C40 C39 C38 120.4(4) . . ?
C40 C39 H24 119.8 . . ?
C38 C39 H24 119.8 . . ?
C41 C40 C39 120.7(5) . . ?
C41 C40 C44 120.2(5) . . ?
C39 C40 C44 119.1(5) . . ?
C40 C41 C42 118.9(5) . . ?
C40 C41 H25 120.5 . . ?
C42 C41 H25 120.5 . . ?
C43 C42 C41 121.2(5) . . ?
C43 C42 C45 120.7(5) . . ?
C41 C42 C45 118.1(5) . . ?
C42 C43 C38 119.9(4) . . ?
C42 C43 H26 120.0 . . ?
C38 C43 H26 120.0 . . ?
F8 C44 F7 106.1(5) . . ?
F8 C44 F9 107.4(5) . . ?
F7 C44 F9 104.9(4) . . ?
F8 C44 C40 112.7(5) . . ?
F7 C44 C40 113.4(5) . . ?
F9 C44 C40 111.7(5) . . ?
F11 C45 F10 107.8(6) . . ?
F11 C45 F12 104.1(6) . . ?
F10 C45 F12 104.0(5) . . ?
F11 C45 C42 115.4(5) . . ?
F10 C45 C42 112.6(5) . . ?
F12 C45 C42 112.0(6) . . ?
C47 C46 C51 117.4(4) . . ?
C47 C46 C33 121.2(4) . . ?
C51 C46 C33 121.4(4) . . ?
C48 C47 C46 121.9(4) . . ?
C48 C47 H27 119.1 . . ?
C46 C47 H27 119.1 . . ?
C47 C48 C49 120.4(4) . . ?
C47 C48 H28 119.8 . . ?
C49 C48 H28 119.8 . . ?
N8 C49 C48 120.8(4) . . ?
N8 C49 C50 121.2(4) . . ?
C48 C49 C50 118.0(4) . . ?
C51 C50 C49 121.1(4) . . ?
C51 C50 H29 119.5 . . ?
C49 C50 H29 119.5 . . ?
C50 C51 C46 121.2(4) . . ?
C50 C51 H30 119.4 . . ?
C46 C51 H30 119.4 . . ?
N8 C52 H31 109.5 . . ?
N8 C52 H32 109.5 . . ?
H31 C52 H32 109.5 . . ?
N8 C52 H33 109.5 . . ?
H31 C52 H33 109.5 . . ?
H32 C52 H33 109.5 . . ?
N8 C53 H34 109.5 . . ?
N8 C53 H35 109.5 . . ?
H34 C53 H35 109.5 . . ?
N8 C53 H36 109.5 . . ?
H34 C53 H36 109.5 . . ?
H35 C53 H36 109.5 . . ?
C1 N1 C4 112.2(4) . . ?
C1 N1 Ni1 116.8(3) . . ?
C4 N1 Ni1 130.7(3) . . ?
C6 N2 C9 111.7(4) . . ?
C6 N2 Ni1 131.4(3) . . ?
C9 N2 Ni1 116.2(3) . . ?
C13 N3 C17 117.8(12) . . ?
C13 N3 C18 122.8(10) . . ?
C17 N3 C18 118.0(11) . . ?
C23 N4 C20 111.3(4) . . ?
C23 N4 Ni2 131.4(3) . . ?
C20 N4 Ni2 117.2(3) . . ?
C28 N5 C25 110.8(4) . . ?
C28 N5 Ni2 116.7(3) . . ?
C25 N5 Ni2 130.8(3) . . ?
C29 N6 C32 111.3(4) . . ?
C29 N6 Ni2 115.8(3) . . ?
C32 N6 Ni2 130.8(3) . . ?
C37 N7 C34 111.9(4) . . ?
C37 N7 Ni2 117.4(3) . . ?
C34 N7 Ni2 130.7(3) . . ?
C49 N8 C53 118.5(4) . . ?
C49 N8 C52 118.5(4) . . ?
C53 N8 C52 117.0(5) . . ?
N2 Ni1 N2 180.0 . 3_757 ?
N2 Ni1 N1 85.70(16) . 3_757 ?
N2 Ni1 N1 94.30(16) 3_757 3_757 ?
N2 Ni1 N1 94.30(16) . . ?
N2 Ni1 N1 85.70(16) 3_757 . ?
N1 Ni1 N1 180.0 3_757 . ?
N4 Ni2 N7 85.13(16) . . ?
N4 Ni2 N5 94.19(16) . . ?
N7 Ni2 N5 173.51(16) . . ?
N4 Ni2 N6 173.56(16) . . ?
N7 Ni2 N6 93.99(16) . . ?
N5 Ni2 N6 85.96(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 C1 C2 C3 -0.6(5) . . . . ?
C9 C1 C2 C3 175.7(5) 3_757 . . . ?
C1 C2 C3 C4 0.8(5) . . . . ?
C2 C3 C4 N1 -0.7(5) . . . . ?
C2 C3 C4 C5 -179.3(5) . . . . ?
N1 C4 C5 C6 -3.1(6) . . . . ?
C3 C4 C5 C6 175.3(4) . . . . ?
N1 C4 C5 C10 176.2(4) . . . . ?
C3 C4 C5 C10 -5.4(7) . . . . ?
C4 C5 C6 N2 -3.0(6) . . . . ?
C10 C5 C6 N2 177.6(4) . . . . ?
C4 C5 C6 C7 174.8(4) . . . . ?
C10 C5 C6 C7 -4.5(7) . . . . ?
N2 C6 C7 C8 0.2(5) . . . . ?
C5 C6 C7 C8 -177.9(4) . . . . ?
C6 C7 C8 C9 0.5(5) . . . . ?
C7 C8 C9 N2 -1.0(5) . . . . ?
C7 C8 C9 C1 175.8(5) . . . 3_757 ?
C4 C5 C10 C15 143.6(4) . . . . ?
C6 C5 C10 C15 -37.0(6) . . . . ?
C4 C5 C10 C11 -39.4(6) . . . . ?
C6 C5 C10 C11 140.0(4) . . . . ?
C15 C10 C11 C12 -0.4(7) . . . . ?
C5 C10 C11 C12 -177.6(4) . . . . ?
C10 C11 C12 C13 1.2(8) . . . . ?
C10 C11 C12 C16 178.0(6) . . . . ?
C11 C12 C13 N3 -173.4(8) . . . . ?
C16 C12 C13 N3 9.8(12) . . . . ?
C11 C12 C13 C14 0.3(8) . . . . ?
C16 C12 C13 C14 -176.5(7) . . . . ?
N3 C13 C14 C15 171.8(7) . . . . ?
C12 C13 C14 C15 -2.6(8) . . . . ?
N3 C13 C14 C19 -12.1(11) . . . . ?
C12 C13 C14 C19 173.5(8) . . . . ?
C13 C14 C15 C10 3.4(8) . . . . ?
C19 C14 C15 C10 -172.1(9) . . . . ?
C11 C10 C15 C14 -1.8(7) . . . . ?
C5 C10 C15 C14 175.4(4) . . . . ?
C11 C12 C16 F3 -165.7(9) . . . . ?
C13 C12 C16 F3 11.1(13) . . . . ?
C11 C12 C16 F2 73.9(10) . . . . ?
C13 C12 C16 F2 -109.2(8) . . . . ?
C11 C12 C16 F1 -42.9(11) . . . . ?
C13 C12 C16 F1 133.9(8) . . . . ?
C13 C14 C19 F5 117.3(10) . . . . ?
C15 C14 C19 F5 -66.9(15) . . . . ?
C13 C14 C19 F4 -5.8(18) . . . . ?
C15 C14 C19 F4 170.1(11) . . . . ?
C13 C14 C19 F6 -129.4(9) . . . . ?
C15 C14 C19 F6 46.4(15) . . . . ?
N4 C20 C21 C22 -1.0(5) . . . . ?
C37 C20 C21 C22 174.5(6) . . . . ?
C20 C21 C22 C23 -0.1(5) . . . . ?
C21 C22 C23 N4 1.2(5) . . . . ?
C21 C22 C23 C24 -175.4(5) . . . . ?
N4 C23 C24 C25 3.7(6) . . . . ?
C22 C23 C24 C25 179.9(5) . . . . ?
N4 C23 C24 C38 -170.3(4) . . . . ?
C22 C23 C24 C38 6.0(7) . . . . ?
C23 C24 C25 N5 -0.6(6) . . . . ?
C38 C24 C25 N5 173.1(4) . . . . ?
C23 C24 C25 C26 -170.3(4) . . . . ?
C38 C24 C25 C26 3.5(7) . . . . ?
N5 C25 C26 C27 -3.3(5) . . . . ?
C24 C25 C26 C27 167.3(4) . . . . ?
C25 C26 C27 C28 1.1(5) . . . . ?
C26 C27 C28 N5 1.6(5) . . . . ?
C26 C27 C28 C29 -169.4(5) . . . . ?
N5 C28 C29 N6 2.4(5) . . . . ?
C27 C28 C29 N6 173.2(5) . . . . ?
N5 C28 C29 C30 -166.9(5) . . . . ?
C27 C28 C29 C30 3.9(10) . . . . ?
N6 C29 C30 C31 0.3(5) . . . . ?
C28 C29 C30 C31 169.8(5) . . . . ?
C29 C30 C31 C32 -0.7(5) . . . . ?
C30 C31 C32 N6 0.9(5) . . . . ?
C30 C31 C32 C33 -168.4(4) . . . . ?
N6 C32 C33 C34 -5.1(6) . . . . ?
C31 C32 C33 C34 163.0(4) . . . . ?
N6 C32 C33 C46 178.2(4) . . . . ?
C31 C32 C33 C46 -13.7(7) . . . . ?
C32 C33 C34 N7 -0.7(6) . . . . ?
C46 C33 C34 N7 176.0(4) . . . . ?
C32 C33 C34 C35 179.9(4) . . . . ?
C46 C33 C34 C35 -3.4(7) . . . . ?
N7 C34 C35 C36 -1.9(5) . . . . ?
C33 C34 C35 C36 177.6(4) . . . . ?
C34 C35 C36 C37 0.9(5) . . . . ?
C35 C36 C37 N7 0.4(5) . . . . ?
C35 C36 C37 C20 -176.3(5) . . . . ?
N4 C20 C37 N7 1.5(5) . . . . ?
C21 C20 C37 N7 -173.9(6) . . . . ?
N4 C20 C37 C36 178.2(6) . . . . ?
C21 C20 C37 C36 2.8(11) . . . . ?
C25 C24 C38 C43 49.8(6) . . . . ?
C23 C24 C38 C43 -136.0(4) . . . . ?
C25 C24 C38 C39 -131.2(4) . . . . ?
C23 C24 C38 C39 43.0(6) . . . . ?
C43 C38 C39 C40 2.2(7) . . . . ?
C24 C38 C39 C40 -176.8(4) . . . . ?
C38 C39 C40 C41 -2.2(7) . . . . ?
C38 C39 C40 C44 179.2(5) . . . . ?
C39 C40 C41 C42 1.1(8) . . . . ?
C44 C40 C41 C42 179.7(5) . . . . ?
C40 C41 C42 C43 -0.1(8) . . . . ?
C40 C41 C42 C45 -177.1(6) . . . . ?
C41 C42 C43 C38 0.1(8) . . . . ?
C45 C42 C43 C38 177.0(5) . . . . ?
C39 C38 C43 C42 -1.1(7) . . . . ?
C24 C38 C43 C42 177.9(4) . . . . ?
C41 C40 C44 F8 147.7(6) . . . . ?
C39 C40 C44 F8 -33.7(8) . . . . ?
C41 C40 C44 F7 -91.7(6) . . . . ?
C39 C40 C44 F7 86.9(6) . . . . ?
C41 C40 C44 F9 26.6(8) . . . . ?
C39 C40 C44 F9 -154.8(5) . . . . ?
C43 C42 C45 F11 156.2(6) . . . . ?
C41 C42 C45 F11 -26.7(9) . . . . ?
C43 C42 C45 F10 31.9(8) . . . . ?
C41 C42 C45 F10 -151.1(5) . . . . ?
C43 C42 C45 F12 -84.9(7) . . . . ?
C41 C42 C45 F12 92.1(6) . . . . ?
C34 C33 C46 C47 135.5(4) . . . . ?
C32 C33 C46 C47 -47.7(6) . . . . ?
C34 C33 C46 C51 -43.0(6) . . . . ?
C32 C33 C46 C51 133.8(4) . . . . ?
C51 C46 C47 C48 3.8(6) . . . . ?
C33 C46 C47 C48 -174.7(4) . . . . ?
C46 C47 C48 C49 -3.5(7) . . . . ?
C47 C48 C49 N8 -176.3(5) . . . . ?
C47 C48 C49 C50 0.8(7) . . . . ?
N8 C49 C50 C51 178.5(5) . . . . ?
C48 C49 C50 C51 1.4(7) . . . . ?
C49 C50 C51 C46 -1.0(7) . . . . ?
C47 C46 C51 C50 -1.6(6) . . . . ?
C33 C46 C51 C50 176.9(4) . . . . ?
C2 C1 N1 C4 0.2(5) . . . . ?
C9 C1 N1 C4 -177.3(3) 3_757 . . . ?
C2 C1 N1 Ni1 174.5(3) . . . . ?
C9 C1 N1 Ni1 -3.0(4) 3_757 . . . ?
C5 C4 N1 C1 179.1(4) . . . . ?
C3 C4 N1 C1 0.3(5) . . . . ?
C5 C4 N1 Ni1 5.8(6) . . . . ?
C3 C4 N1 Ni1 -173.0(3) . . . . ?
C7 C6 N2 C9 -0.8(5) . . . . ?
C5 C6 N2 C9 177.6(4) . . . . ?
C7 C6 N2 Ni1 -171.0(3) . . . . ?
C5 C6 N2 Ni1 7.4(6) . . . . ?
C8 C9 N2 C6 1.1(5) . . . . ?
C1 C9 N2 C6 -176.8(3) 3_757 . . . ?
C8 C9 N2 Ni1 173.0(3) . . . . ?
C1 C9 N2 Ni1 -5.0(4) 3_757 . . . ?
C14 C13 N3 C17 -174.1(11) . . . . ?
C12 C13 N3 C17 -0.2(16) . . . . ?
C14 C13 N3 C18 19.9(15) . . . . ?
C12 C13 N3 C18 -166.2(11) . . . . ?
C22 C23 N4 C20 -1.9(5) . . . . ?
C24 C23 N4 C20 175.3(4) . . . . ?
C22 C23 N4 Ni2 -179.9(3) . . . . ?
C24 C23 N4 Ni2 -2.7(6) . . . . ?
C21 C20 N4 C23 1.9(5) . . . . ?
C37 C20 N4 C23 -175.3(3) . . . . ?
C21 C20 N4 Ni2 -179.8(3) . . . . ?
C37 C20 N4 Ni2 3.0(5) . . . . ?
C27 C28 N5 C25 -3.8(5) . . . . ?
C29 C28 N5 C25 170.1(3) . . . . ?
C27 C28 N5 Ni2 -170.3(3) . . . . ?
C29 C28 N5 Ni2 3.6(4) . . . . ?
C24 C25 N5 C28 -167.8(4) . . . . ?
C26 C25 N5 C28 4.5(5) . . . . ?
C24 C25 N5 Ni2 -3.8(6) . . . . ?
C26 C25 N5 Ni2 168.5(3) . . . . ?
C30 C29 N6 C32 0.3(5) . . . . ?
C28 C29 N6 C32 -172.8(3) . . . . ?
C30 C29 N6 Ni2 165.7(3) . . . . ?
C28 C29 N6 Ni2 -7.4(4) . . . . ?
C31 C32 N6 C29 -0.7(5) . . . . ?
C33 C32 N6 C29 170.1(4) . . . . ?
C31 C32 N6 Ni2 -163.2(3) . . . . ?
C33 C32 N6 Ni2 7.6(6) . . . . ?
C36 C37 N7 C34 -1.7(5) . . . . ?
C20 C37 N7 C34 176.2(3) . . . . ?
C36 C37 N7 Ni2 176.6(3) . . . . ?
C20 C37 N7 Ni2 -5.5(4) . . . . ?
C33 C34 N7 C37 -177.3(4) . . . . ?
C35 C34 N7 C37 2.2(4) . . . . ?
C33 C34 N7 Ni2 4.6(6) . . . . ?
C35 C34 N7 Ni2 -175.8(3) . . . . ?
C48 C49 N8 C53 -169.8(5) . . . . ?
C50 C49 N8 C53 13.2(8) . . . . ?
C48 C49 N8 C52 -17.9(8) . . . . ?
C50 C49 N8 C52 165.1(5) . . . . ?
C6 N2 Ni1 N1 175.4(4) . . . 3_757 ?
C9 N2 Ni1 N1 5.5(3) . . . 3_757 ?
C6 N2 Ni1 N1 -4.6(4) . . . . ?
C9 N2 Ni1 N1 -174.5(3) . . . . ?
C1 N1 Ni1 N2 -175.3(3) . . . . ?
C4 N1 Ni1 N2 -2.2(4) . . . . ?
C1 N1 Ni1 N2 4.7(3) . . . 3_757 ?
C4 N1 Ni1 N2 177.8(4) . . . 3_757 ?
C23 N4 Ni2 N7 172.9(4) . . . . ?
C20 N4 Ni2 N7 -5.0(3) . . . . ?
C23 N4 Ni2 N5 -0.6(4) . . . . ?
C20 N4 Ni2 N5 -178.5(3) . . . . ?
C37 N7 Ni2 N4 6.0(3) . . . . ?
C34 N7 Ni2 N4 -176.1(4) . . . . ?
C37 N7 Ni2 N6 179.6(3) . . . . ?
C34 N7 Ni2 N6 -2.5(4) . . . . ?
C28 N5 Ni2 N4 167.2(3) . . . . ?
C25 N5 Ni2 N4 3.9(4) . . . . ?
C28 N5 Ni2 N6 -6.3(3) . . . . ?
C25 N5 Ni2 N6 -169.6(4) . . . . ?
C29 N6 Ni2 N7 -165.7(3) . . . . ?
C32 N6 Ni2 N7 -3.8(4) . . . . ?
C29 N6 Ni2 N5 7.8(3) . . . . ?
C32 N6 Ni2 N5 169.7(4) . . . . ?

_refine_diff_density_max         1.166
_refine_diff_density_min         -0.470
_refine_diff_density_rms         0.076

_shelxl_version_number           2014-3



