# Electronic Supplementary Material (ESI) for Inorganic Chemistry Frontiers.
# This journal is © the Partner Organisations 2022

####################################################################### 
# 
# 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_l20517
_database_code_depnum_ccdc_archive 'CCDC 2118410'
loop_
_audit_author_name
_audit_author_address
'Liviu Mirica'
;University of Illinois at Urbana Champaign
United States of America
;
_audit_update_record             
;
2021-10-29 deposited with the CCDC.	2022-01-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H24 Br2 N4 Ni'
_chemical_formula_sum            'C14 H24 Br2 N4 Ni'
_chemical_formula_weight         466.90

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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'

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

_cell_length_a                   14.5110(8)
_cell_length_b                   7.7903(5)
_cell_length_c                   30.1258(17)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3405.6(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9189
_cell_measurement_theta_min      2.70
_cell_measurement_theta_max      27.42

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.821
_exptl_crystal_F_000             1872
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.418
_exptl_crystal_size_mid          0.295
_exptl_crystal_size_min          0.206
_exptl_absorpt_coefficient_mu    5.831
_shelx_estimated_absorpt_T_min   0.194
_shelx_estimated_absorpt_T_max   0.380
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.1270
_exptl_absorpt_correction_T_max  0.2080
_exptl_absorpt_process_details   'SADABS V2016/2 (Bruker AXS Inc.)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_detector_area_resol_mean 8
_diffrn_reflns_number            32021
_diffrn_reflns_av_unetI/netI     0.0448
_diffrn_reflns_av_R_equivalents  0.0466
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_theta_min         2.615
_diffrn_reflns_theta_max         27.522
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             7798
_reflns_number_gt                6642
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.962
_reflns_Friedel_fraction_max     0.998
_reflns_Friedel_fraction_full    1.000

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    'SHELXT-2013 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
; 
 Refined as a 2-component inversion twin. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0650P)²+17.6576P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
; 
 Refined as an inversion twin. 
;
_refine_ls_abs_structure_Flack   0.49(2)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         7798
_refine_ls_number_parameters     386
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0586
_refine_ls_R_factor_gt           0.0461
_refine_ls_wR_factor_ref         0.1259
_refine_ls_wR_factor_gt          0.1190
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.035
_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
Br1 Br 0.85266(8) 0.04636(18) 0.56165(4) 0.0285(3) Uani 1 1 d . . . . .
Br2 Br 0.92202(7) -0.06337(14) 0.67712(3) 0.0173(2) Uani 1 1 d . . . . .
Ni1 Ni 0.94812(8) 0.19162(17) 0.61849(4) 0.0112(3) Uani 1 1 d . . . . .
N1 N 1.0252(6) 0.2876(11) 0.6680(3) 0.0127(18) Uani 1 1 d . . . . .
N2 N 0.9777(6) 0.4185(12) 0.5782(3) 0.0133(18) Uani 1 1 d . . . . .
N3 N 1.0845(6) 0.1113(11) 0.5967(3) 0.0133(18) Uani 1 1 d . . . . .
N4 N 0.8488(6) 0.3632(12) 0.6500(3) 0.0118(19) Uani 1 1 d . . . . .
C1 C 0.9860(7) 0.3857(14) 0.6994(3) 0.013(2) Uani 1 1 d . . . . .
C2 C 1.0383(7) 0.4467(14) 0.7346(4) 0.015(2) Uani 1 1 d . . . . .
H2 H 1.010644 0.515882 0.756861 0.018 Uiso 1 1 calc R U . . .
C3 C 1.1319(7) 0.4057(15) 0.7371(4) 0.018(2) Uani 1 1 d . . . . .
H3 H 1.168391 0.447142 0.760951 0.022 Uiso 1 1 calc R U . . .
C4 C 1.1715(7) 0.3028(14) 0.7040(3) 0.014(2) Uani 1 1 d . . . . .
H4 H 1.235347 0.275784 0.704577 0.016 Uiso 1 1 calc R U . . .
C5 C 1.1151(7) 0.2416(13) 0.6704(3) 0.013(2) Uani 1 1 d . . . . .
C6 C 1.1446(7) 0.1114(13) 0.6361(4) 0.016(2) Uani 1 1 d . . . . .
H6A H 1.208571 0.136624 0.626732 0.020 Uiso 1 1 calc R U . . .
H6B H 1.143971 -0.004362 0.649612 0.020 Uiso 1 1 calc R U . . .
C7 C 1.1146(7) 0.2438(15) 0.5638(4) 0.018(2) Uani 1 1 d . . . . .
H7A H 1.091885 0.211094 0.533959 0.022 Uiso 1 1 calc R U . . .
H7B H 1.182807 0.245774 0.562617 0.022 Uiso 1 1 calc R U . . .
C8 C 1.0802(7) 0.4207(14) 0.5748(3) 0.016(2) Uani 1 1 d . . . . .
H8A H 1.107183 0.459092 0.603288 0.020 Uiso 1 1 calc R U . . .
H8B H 1.099460 0.502271 0.551363 0.020 Uiso 1 1 calc R U . . .
C9 C 0.9402(8) 0.5629(15) 0.6040(4) 0.018(2) Uani 1 1 d . . . . .
H9A H 0.936476 0.666355 0.585032 0.021 Uiso 1 1 calc R U . . .
H9B H 0.981765 0.588801 0.629247 0.021 Uiso 1 1 calc R U . . .
C10 C 0.8447(7) 0.5180(15) 0.6215(4) 0.016(2) Uani 1 1 d . . . . .
H10A H 0.820022 0.615772 0.638771 0.020 Uiso 1 1 calc R U . . .
H10B H 0.802676 0.496689 0.596195 0.020 Uiso 1 1 calc R U . . .
C11 C 0.8833(7) 0.4106(16) 0.6950(4) 0.017(2) Uani 1 1 d . . . . .
H11A H 0.851514 0.339436 0.717503 0.020 Uiso 1 1 calc R U . . .
H11B H 0.868010 0.532268 0.700982 0.020 Uiso 1 1 calc R U . . .
C12 C 1.0865(8) -0.0607(15) 0.5758(4) 0.020(2) Uani 1 1 d . . . . .
H12A H 1.046018 -0.061550 0.549809 0.029 Uiso 1 1 calc R U . . .
H12B H 1.065263 -0.146695 0.597256 0.029 Uiso 1 1 calc R U . . .
H12C H 1.149665 -0.087805 0.566642 0.029 Uiso 1 1 calc R U . . .
C13 C 0.7552(7) 0.2881(15) 0.6548(4) 0.017(2) Uani 1 1 d . . . . .
H13A H 0.758623 0.184273 0.673141 0.026 Uiso 1 1 calc R U . . .
H13B H 0.730890 0.258598 0.625454 0.026 Uiso 1 1 calc R U . . .
H13C H 0.714334 0.371746 0.669068 0.026 Uiso 1 1 calc R U . . .
C14 C 0.9382(9) 0.4237(17) 0.5331(4) 0.023(3) Uani 1 1 d . . . . .
H14A H 0.871225 0.409003 0.534771 0.034 Uiso 1 1 calc R U . . .
H14B H 0.964787 0.330954 0.515187 0.034 Uiso 1 1 calc R U . . .
H14C H 0.952386 0.534472 0.519250 0.034 Uiso 1 1 calc R U . . .
Br1A Br 0.91374(8) 0.45993(18) 0.93641(4) 0.0273(3) Uani 1 1 d . . . . .
Br2A Br 0.84555(7) 0.56573(14) 0.82133(3) 0.0170(2) Uani 1 1 d . . . . .
Ni1A Ni 0.81940(8) 0.31107(17) 0.88040(4) 0.0117(3) Uani 1 1 d . . . . .
N1A N 0.7421(6) 0.2155(11) 0.8313(3) 0.0104(17) Uani 1 1 d . . . . .
N2A N 0.7899(6) 0.0874(12) 0.9211(3) 0.0143(18) Uani 1 1 d . . . . .
N3A N 0.9200(6) 0.1380(13) 0.8491(3) 0.0132(19) Uani 1 1 d . . . . .
N4A N 0.6838(6) 0.3894(12) 0.9026(3) 0.0147(18) Uani 1 1 d . . . . .
C1A C 0.6520(7) 0.2595(15) 0.8286(4) 0.018(2) Uani 1 1 d . . . . .
C2A C 0.5980(7) 0.1968(14) 0.7941(4) 0.016(2) Uani 1 1 d . . . . .
H2A H 0.534449 0.225676 0.792578 0.019 Uiso 1 1 calc R U . . .
C3A C 0.6365(8) 0.0931(15) 0.7624(4) 0.019(2) Uani 1 1 d . . . . .
H3A H 0.599607 0.049370 0.738932 0.023 Uiso 1 1 calc R U . . .
C4A C 0.7295(8) 0.0520(15) 0.7645(3) 0.016(2) Uani 1 1 d . . . . .
H4A H 0.757414 -0.017744 0.742404 0.019 Uiso 1 1 calc R U . . .
C5A C 0.7812(7) 0.1165(14) 0.8004(3) 0.012(2) Uani 1 1 d . . . . .
C6A C 0.8831(7) 0.0863(15) 0.8047(4) 0.015(2) Uani 1 1 d . . . . .
H6AA H 0.896106 -0.037059 0.799817 0.018 Uiso 1 1 calc R U . . .
H6AB H 0.915635 0.151960 0.781310 0.018 Uiso 1 1 calc R U . . .
C7A C 0.9245(7) -0.0130(15) 0.8800(5) 0.019(2) Uani 1 1 d . . . . .
H7AA H 0.964167 0.015704 0.905722 0.023 Uiso 1 1 calc R U . . .
H7AB H 0.952281 -0.112168 0.864442 0.023 Uiso 1 1 calc R U . . .
C8A C 0.8292(8) -0.0605(15) 0.8962(4) 0.017(2) Uani 1 1 d . . . . .
H8AA H 0.789136 -0.089092 0.870683 0.020 Uiso 1 1 calc R U . . .
H8AB H 0.832748 -0.162255 0.915843 0.020 Uiso 1 1 calc R U . . .
C9A C 0.6870(7) 0.0806(15) 0.9235(4) 0.017(2) Uani 1 1 d . . . . .
H9AA H 0.667662 -0.002857 0.946419 0.021 Uiso 1 1 calc R U . . .
H9AB H 0.661574 0.043004 0.894560 0.021 Uiso 1 1 calc R U . . .
C10A C 0.6512(7) 0.2563(15) 0.9348(4) 0.017(2) Uani 1 1 d . . . . .
H10C H 0.583028 0.253995 0.934878 0.021 Uiso 1 1 calc R U . . .
H10D H 0.672022 0.287703 0.965053 0.021 Uiso 1 1 calc R U . . .
C11A C 0.6247(7) 0.3911(15) 0.8619(3) 0.014(2) Uani 1 1 d . . . . .
H11C H 0.559884 0.371100 0.870712 0.017 Uiso 1 1 calc R U . . .
H11D H 0.628272 0.506132 0.848043 0.017 Uiso 1 1 calc R U . . .
C12A C 1.0112(7) 0.2142(14) 0.8445(4) 0.017(2) Uani 1 1 d . . . . .
H12D H 1.036497 0.238509 0.873986 0.026 Uiso 1 1 calc R U . . .
H12E H 1.006501 0.321347 0.827572 0.026 Uiso 1 1 calc R U . . .
H12F H 1.051892 0.134191 0.828828 0.026 Uiso 1 1 calc R U . . .
C13A C 0.6780(8) 0.5623(15) 0.9231(4) 0.022(2) Uani 1 1 d . . . . .
H13D H 0.704243 0.647590 0.902803 0.032 Uiso 1 1 calc R U . . .
H13E H 0.712641 0.562970 0.951039 0.032 Uiso 1 1 calc R U . . .
H13F H 0.613364 0.590505 0.929028 0.032 Uiso 1 1 calc R U . . .
C14A C 0.8265(8) 0.0830(18) 0.9673(4) 0.022(3) Uani 1 1 d . . . . .
H14D H 0.800473 0.178567 0.984312 0.034 Uiso 1 1 calc R U . . .
H14E H 0.893839 0.093338 0.966602 0.034 Uiso 1 1 calc R U . . .
H14F H 0.809405 -0.025865 0.981354 0.034 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 Ni1 2.4761(18) . ?
Br2 Ni1 2.6851(18) . ?
Ni1 N1 2.008(9) . ?
Ni1 N3 2.178(8) . ?
Ni1 N4 2.183(9) . ?
Ni1 N2 2.187(9) . ?
N1 C1 1.343(13) . ?
N1 C5 1.354(13) . ?
N2 C9 1.472(15) . ?
N2 C14 1.476(14) . ?
N2 C8 1.491(14) . ?
N3 C6 1.472(14) . ?
N3 C12 1.480(13) . ?
N3 C7 1.496(14) . ?
N4 C10 1.483(15) . ?
N4 C13 1.487(13) . ?
N4 C11 1.490(14) . ?
C1 C2 1.388(15) . ?
C1 C11 1.509(14) . ?
C2 C3 1.397(15) . ?
C2 H2 0.9500 . ?
C3 C4 1.402(15) . ?
C3 H3 0.9500 . ?
C4 C5 1.386(14) . ?
C4 H4 0.9500 . ?
C5 C6 1.511(14) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.503(16) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.523(15) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
Br1A Ni1A 2.4631(18) . ?
Br2A Ni1A 2.6919(18) . ?
Ni1A N1A 2.001(8) . ?
Ni1A N4A 2.166(9) . ?
Ni1A N2A 2.172(10) . ?
Ni1A N3A 2.200(9) . ?
N1A C5A 1.336(13) . ?
N1A C1A 1.354(13) . ?
N2A C8A 1.487(15) . ?
N2A C14A 1.491(15) . ?
N2A C9A 1.496(13) . ?
N3A C12A 1.456(14) . ?
N3A C6A 1.495(14) . ?
N3A C7A 1.503(16) . ?
N4A C13A 1.484(14) . ?
N4A C11A 1.495(13) . ?
N4A C10A 1.497(14) . ?
C1A C2A 1.390(15) . ?
C1A C11A 1.488(15) . ?
C2A C3A 1.371(16) . ?
C2A H2A 0.9500 . ?
C3A C4A 1.388(16) . ?
C3A H3A 0.9500 . ?
C4A C5A 1.408(14) . ?
C4A H4A 0.9500 . ?
C5A C6A 1.504(14) . ?
C6A H6AA 0.9900 . ?
C6A H6AB 0.9900 . ?
C7A C8A 1.513(15) . ?
C7A H7AA 0.9900 . ?
C7A H7AB 0.9900 . ?
C8A H8AA 0.9900 . ?
C8A H8AB 0.9900 . ?
C9A C10A 1.504(16) . ?
C9A H9AA 0.9900 . ?
C9A H9AB 0.9900 . ?
C10A H10C 0.9900 . ?
C10A H10D 0.9900 . ?
C11A H11C 0.9900 . ?
C11A H11D 0.9900 . ?
C12A H12D 0.9800 . ?
C12A H12E 0.9800 . ?
C12A H12F 0.9800 . ?
C13A H13D 0.9800 . ?
C13A H13E 0.9800 . ?
C13A H13F 0.9800 . ?
C14A H14D 0.9800 . ?
C14A H14E 0.9800 . ?
C14A H14F 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 Ni1 N3 79.9(3) . . ?
N1 Ni1 N4 79.4(3) . . ?
N3 Ni1 N4 155.1(3) . . ?
N1 Ni1 N2 90.1(3) . . ?
N3 Ni1 N2 83.5(3) . . ?
N4 Ni1 N2 82.9(3) . . ?
N1 Ni1 Br1 174.3(3) . . ?
N3 Ni1 Br1 99.7(2) . . ?
N4 Ni1 Br1 102.2(2) . . ?
N2 Ni1 Br1 95.5(2) . . ?
N1 Ni1 Br2 82.3(2) . . ?
N3 Ni1 Br2 96.6(2) . . ?
N4 Ni1 Br2 94.2(3) . . ?
N2 Ni1 Br2 172.2(2) . . ?
Br1 Ni1 Br2 92.17(6) . . ?
C1 N1 C5 121.3(9) . . ?
C1 N1 Ni1 119.9(7) . . ?
C5 N1 Ni1 118.6(7) . . ?
C9 N2 C14 108.9(9) . . ?
C9 N2 C8 113.4(8) . . ?
C14 N2 C8 108.9(8) . . ?
C9 N2 Ni1 104.6(7) . . ?
C14 N2 Ni1 117.2(7) . . ?
C8 N2 Ni1 104.1(6) . . ?
C6 N3 C12 109.3(8) . . ?
C6 N3 C7 111.1(8) . . ?
C12 N3 C7 109.8(9) . . ?
C6 N3 Ni1 107.1(6) . . ?
C12 N3 Ni1 114.0(7) . . ?
C7 N3 Ni1 105.5(6) . . ?
C10 N4 C13 109.9(8) . . ?
C10 N4 C11 109.8(9) . . ?
C13 N4 C11 108.4(9) . . ?
C10 N4 Ni1 105.8(7) . . ?
C13 N4 Ni1 113.8(7) . . ?
C11 N4 Ni1 109.0(6) . . ?
N1 C1 C2 120.1(9) . . ?
N1 C1 C11 115.5(9) . . ?
C2 C1 C11 124.3(10) . . ?
C1 C2 C3 119.6(10) . . ?
C1 C2 H2 120.2 . . ?
C3 C2 H2 120.2 . . ?
C2 C3 C4 119.4(10) . . ?
C2 C3 H3 120.3 . . ?
C4 C3 H3 120.3 . . ?
C5 C4 C3 118.2(10) . . ?
C5 C4 H4 120.9 . . ?
C3 C4 H4 120.9 . . ?
N1 C5 C4 121.2(10) . . ?
N1 C5 C6 114.4(9) . . ?
C4 C5 C6 124.3(9) . . ?
N3 C6 C5 112.6(8) . . ?
N3 C6 H6A 109.1 . . ?
C5 C6 H6A 109.1 . . ?
N3 C6 H6B 109.1 . . ?
C5 C6 H6B 109.1 . . ?
H6A C6 H6B 107.8 . . ?
N3 C7 C8 112.9(8) . . ?
N3 C7 H7A 109.0 . . ?
C8 C7 H7A 109.0 . . ?
N3 C7 H7B 109.0 . . ?
C8 C7 H7B 109.0 . . ?
H7A C7 H7B 107.8 . . ?
N2 C8 C7 109.7(9) . . ?
N2 C8 H8A 109.7 . . ?
C7 C8 H8A 109.7 . . ?
N2 C8 H8B 109.7 . . ?
C7 C8 H8B 109.7 . . ?
H8A C8 H8B 108.2 . . ?
N2 C9 C10 110.1(9) . . ?
N2 C9 H9A 109.7 . . ?
C10 C9 H9A 109.7 . . ?
N2 C9 H9B 109.7 . . ?
C10 C9 H9B 109.7 . . ?
H9A C9 H9B 108.2 . . ?
N4 C10 C9 110.5(9) . . ?
N4 C10 H10A 109.5 . . ?
C9 C10 H10A 109.5 . . ?
N4 C10 H10B 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 108.1 . . ?
N4 C11 C1 112.3(8) . . ?
N4 C11 H11A 109.1 . . ?
C1 C11 H11A 109.1 . . ?
N4 C11 H11B 109.1 . . ?
C1 C11 H11B 109.1 . . ?
H11A C11 H11B 107.9 . . ?
N3 C12 H12A 109.5 . . ?
N3 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
N3 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N4 C13 H13A 109.5 . . ?
N4 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
N4 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N2 C14 H14A 109.5 . . ?
N2 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
N2 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N1A Ni1A N4A 79.8(3) . . ?
N1A Ni1A N2A 90.5(3) . . ?
N4A Ni1A N2A 82.7(3) . . ?
N1A Ni1A N3A 80.0(3) . . ?
N4A Ni1A N3A 155.2(4) . . ?
N2A Ni1A N3A 83.2(4) . . ?
N1A Ni1A Br1A 173.5(3) . . ?
N4A Ni1A Br1A 99.2(3) . . ?
N2A Ni1A Br1A 95.8(2) . . ?
N3A Ni1A Br1A 102.3(2) . . ?
N1A Ni1A Br2A 82.2(2) . . ?
N4A Ni1A Br2A 97.1(2) . . ?
N2A Ni1A Br2A 172.6(2) . . ?
N3A Ni1A Br2A 94.3(3) . . ?
Br1A Ni1A Br2A 91.58(6) . . ?
C5A N1A C1A 121.0(9) . . ?
C5A N1A Ni1A 119.5(7) . . ?
C1A N1A Ni1A 119.4(7) . . ?
C8A N2A C14A 108.4(9) . . ?
C8A N2A C9A 112.3(9) . . ?
C14A N2A C9A 108.0(8) . . ?
C8A N2A Ni1A 105.2(7) . . ?
C14A N2A Ni1A 118.4(8) . . ?
C9A N2A Ni1A 104.6(7) . . ?
C12A N3A C6A 110.5(9) . . ?
C12A N3A C7A 109.8(8) . . ?
C6A N3A C7A 111.1(9) . . ?
C12A N3A Ni1A 113.2(7) . . ?
C6A N3A Ni1A 108.1(6) . . ?
C7A N3A Ni1A 104.0(7) . . ?
C13A N4A C11A 107.5(9) . . ?
C13A N4A C10A 109.9(9) . . ?
C11A N4A C10A 110.9(8) . . ?
C13A N4A Ni1A 115.8(7) . . ?
C11A N4A Ni1A 105.7(6) . . ?
C10A N4A Ni1A 107.0(6) . . ?
N1A C1A C2A 120.0(10) . . ?
N1A C1A C11A 113.0(9) . . ?
C2A C1A C11A 126.6(10) . . ?
C3A C2A C1A 119.9(10) . . ?
C3A C2A H2A 120.1 . . ?
C1A C2A H2A 120.1 . . ?
C2A C3A C4A 120.0(10) . . ?
C2A C3A H3A 120.0 . . ?
C4A C3A H3A 120.0 . . ?
C3A C4A C5A 118.1(10) . . ?
C3A C4A H4A 121.0 . . ?
C5A C4A H4A 121.0 . . ?
N1A C5A C4A 121.0(9) . . ?
N1A C5A C6A 116.6(9) . . ?
C4A C5A C6A 122.3(9) . . ?
N3A C6A C5A 112.8(8) . . ?
N3A C6A H6AA 109.0 . . ?
C5A C6A H6AA 109.0 . . ?
N3A C6A H6AB 109.0 . . ?
C5A C6A H6AB 109.0 . . ?
H6AA C6A H6AB 107.8 . . ?
N3A C7A C8A 110.6(9) . . ?
N3A C7A H7AA 109.5 . . ?
C8A C7A H7AA 109.5 . . ?
N3A C7A H7AB 109.5 . . ?
C8A C7A H7AB 109.5 . . ?
H7AA C7A H7AB 108.1 . . ?
N2A C8A C7A 108.8(9) . . ?
N2A C8A H8AA 109.9 . . ?
C7A C8A H8AA 109.9 . . ?
N2A C8A H8AB 109.9 . . ?
C7A C8A H8AB 109.9 . . ?
H8AA C8A H8AB 108.3 . . ?
N2A C9A C10A 108.9(9) . . ?
N2A C9A H9AA 109.9 . . ?
C10A C9A H9AA 109.9 . . ?
N2A C9A H9AB 109.9 . . ?
C10A C9A H9AB 109.9 . . ?
H9AA C9A H9AB 108.3 . . ?
N4A C10A C9A 112.0(9) . . ?
N4A C10A H10C 109.2 . . ?
C9A C10A H10C 109.2 . . ?
N4A C10A H10D 109.2 . . ?
C9A C10A H10D 109.2 . . ?
H10C C10A H10D 107.9 . . ?
C1A C11A N4A 113.2(9) . . ?
C1A C11A H11C 108.9 . . ?
N4A C11A H11C 108.9 . . ?
C1A C11A H11D 108.9 . . ?
N4A C11A H11D 108.9 . . ?
H11C C11A H11D 107.7 . . ?
N3A C12A H12D 109.5 . . ?
N3A C12A H12E 109.5 . . ?
H12D C12A H12E 109.5 . . ?
N3A C12A H12F 109.5 . . ?
H12D C12A H12F 109.5 . . ?
H12E C12A H12F 109.5 . . ?
N4A C13A H13D 109.5 . . ?
N4A C13A H13E 109.5 . . ?
H13D C13A H13E 109.5 . . ?
N4A C13A H13F 109.5 . . ?
H13D C13A H13F 109.5 . . ?
H13E C13A H13F 109.5 . . ?
N2A C14A H14D 109.5 . . ?
N2A C14A H14E 109.5 . . ?
H14D C14A H14E 109.5 . . ?
N2A C14A H14F 109.5 . . ?
H14D C14A H14F 109.5 . . ?
H14E C14A H14F 109.5 . . ?

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
C5 N1 C1 C2 2.0(15) . . . . ?
Ni1 N1 C1 C2 177.4(8) . . . . ?
C5 N1 C1 C11 -173.6(9) . . . . ?
Ni1 N1 C1 C11 1.9(12) . . . . ?
N1 C1 C2 C3 0.1(16) . . . . ?
C11 C1 C2 C3 175.3(11) . . . . ?
C1 C2 C3 C4 -0.3(17) . . . . ?
C2 C3 C4 C5 -1.7(16) . . . . ?
C1 N1 C5 C4 -4.1(15) . . . . ?
Ni1 N1 C5 C4 -179.5(8) . . . . ?
C1 N1 C5 C6 171.8(9) . . . . ?
Ni1 N1 C5 C6 -3.7(11) . . . . ?
C3 C4 C5 N1 3.8(15) . . . . ?
C3 C4 C5 C6 -171.6(10) . . . . ?
C12 N3 C6 C5 -153.1(9) . . . . ?
C7 N3 C6 C5 85.6(10) . . . . ?
Ni1 N3 C6 C5 -29.1(10) . . . . ?
N1 C5 C6 N3 23.2(12) . . . . ?
C4 C5 C6 N3 -161.1(10) . . . . ?
C6 N3 C7 C8 -81.8(11) . . . . ?
C12 N3 C7 C8 157.2(9) . . . . ?
Ni1 N3 C7 C8 33.9(10) . . . . ?
C9 N2 C8 C7 159.0(9) . . . . ?
C14 N2 C8 C7 -79.7(11) . . . . ?
Ni1 N2 C8 C7 45.9(9) . . . . ?
N3 C7 C8 N2 -56.7(12) . . . . ?
C14 N2 C9 C10 80.9(11) . . . . ?
C8 N2 C9 C10 -157.8(9) . . . . ?
Ni1 N2 C9 C10 -45.1(10) . . . . ?
C13 N4 C10 C9 -161.8(9) . . . . ?
C11 N4 C10 C9 79.0(11) . . . . ?
Ni1 N4 C10 C9 -38.5(10) . . . . ?
N2 C9 C10 N4 59.3(12) . . . . ?
C10 N4 C11 C1 -94.3(11) . . . . ?
C13 N4 C11 C1 145.5(10) . . . . ?
Ni1 N4 C11 C1 21.1(11) . . . . ?
N1 C1 C11 N4 -16.2(14) . . . . ?
C2 C1 C11 N4 168.5(10) . . . . ?
C5A N1A C1A C2A 2.2(16) . . . . ?
Ni1A N1A C1A C2A 178.7(8) . . . . ?
C5A N1A C1A C11A -171.1(9) . . . . ?
Ni1A N1A C1A C11A 5.4(12) . . . . ?
N1A C1A C2A C3A -1.3(16) . . . . ?
C11A C1A C2A C3A 171.1(11) . . . . ?
C1A C2A C3A C4A -0.5(17) . . . . ?
C2A C3A C4A C5A 1.3(17) . . . . ?
C1A N1A C5A C4A -1.3(16) . . . . ?
Ni1A N1A C5A C4A -177.8(8) . . . . ?
C1A N1A C5A C6A 175.6(10) . . . . ?
Ni1A N1A C5A C6A -0.9(12) . . . . ?
C3A C4A C5A N1A -0.5(16) . . . . ?
C3A C4A C5A C6A -177.2(10) . . . . ?
C12A N3A C6A C5A -142.6(9) . . . . ?
C7A N3A C6A C5A 95.3(11) . . . . ?
Ni1A N3A C6A C5A -18.2(11) . . . . ?
N1A C5A C6A N3A 13.8(14) . . . . ?
C4A C5A C6A N3A -169.4(10) . . . . ?
C12A N3A C7A C8A 162.8(9) . . . . ?
C6A N3A C7A C8A -74.6(12) . . . . ?
Ni1A N3A C7A C8A 41.4(11) . . . . ?
C14A N2A C8A C7A -82.3(12) . . . . ?
C9A N2A C8A C7A 158.4(9) . . . . ?
Ni1A N2A C8A C7A 45.2(10) . . . . ?
N3A C7A C8A N2A -61.4(13) . . . . ?
C8A N2A C9A C10A -161.4(9) . . . . ?
C14A N2A C9A C10A 79.2(11) . . . . ?
Ni1A N2A C9A C10A -47.8(9) . . . . ?
C13A N4A C10A C9A -158.8(9) . . . . ?
C11A N4A C10A C9A 82.4(11) . . . . ?
Ni1A N4A C10A C9A -32.3(10) . . . . ?
N2A C9A C10A N4A 55.9(11) . . . . ?
N1A C1A C11A N4A -26.2(13) . . . . ?
C2A C1A C11A N4A 160.9(10) . . . . ?
C13A N4A C11A C1A 156.3(9) . . . . ?
C10A N4A C11A C1A -83.6(11) . . . . ?
Ni1A N4A C11A C1A 32.0(10) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
#C2 H2 Br2A  0.95 3.11 3.939(11) 146.9 . 
#C10 H10A Br2  0.99 3.13 3.834(12) 129.6 1_565 
#C12 H12A Br1  0.98 2.95 3.521(11) 118.2 . 
#C12 H12C Br1  0.98 2.97 3.887(11) 156.8 3 
#C13 H13A Br2  0.98 3.06 3.716(11) 125.6 . 
#C13 H13B Br1  0.98 3.09 3.664(11) 118.8 . 
#C4A H4A Br2  0.95 3.11 3.943(11) 146.6 . 
#C12A H12D Br1A  0.98 3.11 3.651(11) 116.1 . 
#C12A H12E Br2A  0.98 3.02 3.710(11) 128.5 . 
#C13A H13E Br1A  0.98 3.06 3.535(11) 111.3 . 
C13A H13F Br1A 0.98 2.93 3.860(11) 158.4 3_465

_refine_diff_density_max         1.286
_refine_diff_density_min         -1.612
_refine_diff_density_rms         0.162


# start Validation Reply Form
_vrf_PLAT341_l20517              
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.01519 Ang.  
RESPONSE:
Recimic twinning (BASF = 0.49) 
present in the crystal may be responsible for low bond precison. 
;
# end Validation Reply Form

####################################################################### 
# 
# 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_19_a
_database_code_depnum_ccdc_archive 'CCDC 2118411'
loop_
_audit_author_name
_audit_author_address
'Liviu Mirica'
;University of Illinois at Urbana Champaign
United States of America
;
_audit_update_record             
;
2021-10-29 deposited with the CCDC.	2022-01-13 downloaded from the CCDC.
;
_audit_creation_date             2019-12-19
_audit_creation_method           
;
Olex2 1.3
(compiled 2019.09.11 svn.r3662 for OlexSys, GUI svn.r5938)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H36 N4 Ni'
_chemical_formula_sum            'C24 H36 N4 Ni'
_chemical_formula_weight         439.28
_chemical_absolute_configuration ad
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   10.3930(4)
_cell_length_b                   13.3946(5)
_cell_length_c                   15.9835(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2225.06(15)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    46410
_cell_measurement_temperature    100.01
_cell_measurement_theta_max      28.29
_cell_measurement_theta_min      2.48
_shelx_estimated_absorpt_T_max   0.824
_shelx_estimated_absorpt_T_min   0.692
_exptl_absorpt_coefficient_mu    0.889
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6431
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0968 before and 0.0528 after correction.
The Ratio of minimum to maximum transmission is 0.8624.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.311
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             944
_exptl_crystal_size_max          0.446
_exptl_crystal_size_mid          0.297
_exptl_crystal_size_min          0.227
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0344
_diffrn_reflns_av_unetI/netI     0.0164
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            62697
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.294
_diffrn_reflns_theta_min         2.337
_diffrn_ambient_temperature      100.01
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.776
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                5367
_reflns_number_total             5515
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_refine_diff_density_max         0.577
_refine_diff_density_min         -0.188
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details 
;
 Flack x determined using 2314 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.010(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     267
_refine_ls_number_reflns         5515
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0247
_refine_ls_R_factor_gt           0.0237
_refine_ls_restrained_S_all      1.046
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0255P)²+0.9482P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0593
_refine_ls_wR_factor_ref         0.0599
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C7(H7A,H7B), C15(H15A,H15B), C6(H6A,H6B), C4(H4A,H4B),
 C10(H10A,H10B), C9(H9A,H9B)
2.b Aromatic/amide H refined with riding coordinates:
 C20(H20), C1(H1), C23(H23), C22(H22), C21(H21), C2(H2), C14(H14)
2.c Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C8(H8A,H8B,H8C), C18(H18A,H18B,H18C), C5(H5A,H5B,H5C),
 C11(H11A,H11B,H11C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     'dual space'
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Ni1 Ni 0.21264(2) 0.42810(2) 0.54776(2) 0.01957(7) Uani 1 1 d . . . . .
N4 N 0.4749(2) 0.39093(16) 0.75377(12) 0.0288(4) Uani 1 1 d . . . . .
N2 N 0.31362(17) 0.38704(14) 0.44275(11) 0.0259(4) Uani 1 1 d . . . . .
N1 N 0.29262(19) 0.30352(13) 0.59155(11) 0.0230(3) Uani 1 1 d . . . . .
N3 N 0.58744(18) 0.49224(16) 0.54651(14) 0.0324(4) Uani 1 1 d . . . . .
C19 C 0.04078(19) 0.54735(16) 0.64101(13) 0.0209(4) Uani 1 1 d . . . . .
C12 C 0.3410(2) 0.35996(18) 0.73489(14) 0.0258(4) Uani 1 1 d . . . . .
H12A H 0.292526 0.418960 0.714950 0.031 Uiso 1 1 calc R U . . .
H12B H 0.299937 0.336857 0.787304 0.031 Uiso 1 1 calc R U . . .
C3 C 0.3079(2) 0.23657(17) 0.52850(14) 0.0287(5) Uani 1 1 d . . . . .
C24 C 0.08994(19) 0.44921(16) 0.63310(13) 0.0209(4) Uani 1 1 d . . . . .
C16 C 0.0981(2) 0.61980(16) 0.57867(14) 0.0231(4) Uani 1 1 d . . . . .
C7 C 0.5074(2) 0.4985(2) 0.47186(14) 0.0302(5) Uani 1 1 d . . . . .
H7A H 0.558359 0.526245 0.425008 0.036 Uiso 1 1 calc R U . . .
H7B H 0.433975 0.543873 0.482453 0.036 Uiso 1 1 calc R U . . .
C20 C -0.0517(2) 0.5710(2) 0.70083(13) 0.0259(4) Uani 1 1 d . . . . .
H20 H -0.080941 0.637876 0.706277 0.031 Uiso 1 1 calc R U . . .
C17 C 0.0025(2) 0.70077(17) 0.55041(18) 0.0311(5) Uani 1 1 d . . . . .
H17A H -0.076292 0.669074 0.529679 0.047 Uiso 1 1 calc R U . . .
H17B H 0.041279 0.740700 0.505646 0.047 Uiso 1 1 calc R U . . .
H17C H -0.018411 0.744116 0.597897 0.047 Uiso 1 1 calc R U . . .
C13 C 0.3299(2) 0.27760(17) 0.66973(14) 0.0251(4) Uani 1 1 d . . . . .
C1 C 0.3804(2) 0.11126(19) 0.62251(19) 0.0373(6) Uani 1 1 d . . . . .
H1 H 0.406452 0.044633 0.633834 0.045 Uiso 1 1 calc R U . . .
C15 C 0.1422(2) 0.55232(16) 0.50637(13) 0.0234(4) Uani 1 1 d . . . . .
H15A H 0.208362 0.587571 0.472977 0.028 Uiso 1 1 calc R U . . .
H15B H 0.068203 0.537999 0.469288 0.028 Uiso 1 1 calc R U . . .
C6 C 0.4570(2) 0.39504(17) 0.44804(15) 0.0274(4) Uani 1 1 d . . . . .
H6A H 0.493978 0.376215 0.393188 0.033 Uiso 1 1 calc R U . . .
H6B H 0.488316 0.346188 0.489827 0.033 Uiso 1 1 calc R U . . .
C23 C 0.0372(2) 0.37626(17) 0.68586(14) 0.0248(4) Uani 1 1 d . . . . .
H23 H 0.066582 0.309297 0.681556 0.030 Uiso 1 1 calc R U . . .
C4 C 0.2779(2) 0.27929(17) 0.44370(14) 0.0322(5) Uani 1 1 d . . . . .
H4A H 0.326898 0.243002 0.400154 0.039 Uiso 1 1 calc R U . . .
H4B H 0.184982 0.271730 0.431563 0.039 Uiso 1 1 calc R U . . .
C22 C -0.0578(2) 0.39990(19) 0.74472(14) 0.0277(5) Uani 1 1 d . . . . .
H22 H -0.092582 0.349058 0.779436 0.033 Uiso 1 1 calc R U . . .
C21 C -0.1011(2) 0.4973(2) 0.75246(14) 0.0294(5) Uani 1 1 d . . . . .
H21 H -0.164514 0.513446 0.793050 0.035 Uiso 1 1 calc R U . . .
C2 C 0.3534(2) 0.14069(17) 0.54202(19) 0.0358(5) Uani 1 1 d . . . . .
H2 H 0.365622 0.096091 0.496496 0.043 Uiso 1 1 calc R U . . .
C8 C 0.6834(2) 0.5701(2) 0.55313(17) 0.0366(5) Uani 1 1 d . . . . .
H8A H 0.733984 0.572718 0.501415 0.055 Uiso 1 1 calc R U . . .
H8B H 0.740527 0.555884 0.600449 0.055 Uiso 1 1 calc R U . . .
H8C H 0.640813 0.634526 0.562010 0.055 Uiso 1 1 calc R U . . .
C10 C 0.5562(2) 0.4046(2) 0.67986(15) 0.0331(6) Uani 1 1 d . . . . .
H10A H 0.559748 0.341098 0.648193 0.040 Uiso 1 1 calc R U . . .
H10B H 0.644720 0.421017 0.698049 0.040 Uiso 1 1 calc R U . . .
C18 C 0.2160(2) 0.67099(16) 0.61777(15) 0.0287(4) Uani 1 1 d . . . . .
H18A H 0.188978 0.709854 0.666670 0.043 Uiso 1 1 calc R U . . .
H18B H 0.255605 0.715544 0.576530 0.043 Uiso 1 1 calc R U . . .
H18C H 0.278451 0.620236 0.635052 0.043 Uiso 1 1 calc R U . . .
C14 C 0.3692(2) 0.18002(18) 0.68703(17) 0.0326(5) Uani 1 1 d . . . . .
H14 H 0.388268 0.160775 0.742881 0.039 Uiso 1 1 calc R U . . .
C9 C 0.5073(2) 0.4865(2) 0.62281(15) 0.0302(5) Uani 1 1 d . . . . .
H9A H 0.416820 0.472784 0.607142 0.036 Uiso 1 1 calc R U . . .
H9B H 0.509921 0.551293 0.652627 0.036 Uiso 1 1 calc R U . . .
C5 C 0.2712(2) 0.4320(2) 0.36274(13) 0.0349(5) Uani 1 1 d . . . . .
H5A H 0.177021 0.432079 0.360233 0.052 Uiso 1 1 calc R U . . .
H5B H 0.305557 0.392848 0.315976 0.052 Uiso 1 1 calc R U . . .
H5C H 0.303072 0.500686 0.359050 0.052 Uiso 1 1 calc R U . . .
C11 C 0.5419(3) 0.3227(2) 0.81066(18) 0.0411(6) Uani 1 1 d . . . . .
H11A H 0.487334 0.309168 0.859345 0.062 Uiso 1 1 calc R U . . .
H11B H 0.622644 0.353402 0.829184 0.062 Uiso 1 1 calc R U . . .
H11C H 0.560585 0.260034 0.781494 0.062 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ni1 N2 2.0546(18) . ?
Ni1 N1 1.9913(18) . ?
Ni1 C24 1.888(2) . ?
Ni1 C15 1.934(2) . ?
N4 C12 1.483(3) . ?
N4 C10 1.464(3) . ?
N4 C11 1.465(3) . ?
N2 C6 1.496(3) . ?
N2 C4 1.490(3) . ?
N2 C5 1.480(3) . ?
N1 C3 1.358(3) . ?
N1 C13 1.354(3) . ?
N3 C7 1.457(3) . ?
N3 C8 1.448(3) . ?
N3 C9 1.479(3) . ?
C19 C24 1.416(3) . ?
C19 C16 1.513(3) . ?
C19 C20 1.392(3) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 C13 1.522(3) . ?
C3 C4 1.504(3) . ?
C3 C2 1.385(3) . ?
C24 C23 1.402(3) . ?
C16 C17 1.539(3) . ?
C16 C15 1.537(3) . ?
C16 C18 1.537(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C6 1.529(3) . ?
C20 H20 0.9500 . ?
C20 C21 1.386(4) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C13 C14 1.397(3) . ?
C1 H1 0.9500 . ?
C1 C2 1.375(4) . ?
C1 C14 1.387(4) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C23 H23 0.9500 . ?
C23 C22 1.400(3) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C22 H22 0.9500 . ?
C22 C21 1.385(4) . ?
C21 H21 0.9500 . ?
C2 H2 0.9500 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C9 1.515(3) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C14 H14 0.9500 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 Ni1 N2 81.35(7) . . ?
C24 Ni1 N2 167.17(8) . . ?
C24 Ni1 N1 98.83(8) . . ?
C24 Ni1 C15 82.11(9) . . ?
C15 Ni1 N2 98.28(8) . . ?
C15 Ni1 N1 177.36(9) . . ?
C10 N4 C12 114.34(18) . . ?
C10 N4 C11 107.7(2) . . ?
C11 N4 C12 113.5(2) . . ?
C6 N2 Ni1 116.32(14) . . ?
C4 N2 Ni1 97.10(13) . . ?
C4 N2 C6 108.47(18) . . ?
C5 N2 Ni1 116.42(14) . . ?
C5 N2 C6 108.43(18) . . ?
C5 N2 C4 109.16(18) . . ?
C3 N1 Ni1 109.96(15) . . ?
C13 N1 Ni1 131.22(14) . . ?
C13 N1 C3 118.82(19) . . ?
C7 N3 C9 110.88(17) . . ?
C8 N3 C7 114.3(2) . . ?
C8 N3 C9 111.4(2) . . ?
C24 C19 C16 113.23(18) . . ?
C20 C19 C24 121.4(2) . . ?
C20 C19 C16 125.3(2) . . ?
N4 C12 H12A 108.7 . . ?
N4 C12 H12B 108.7 . . ?
N4 C12 C13 114.41(18) . . ?
H12A C12 H12B 107.6 . . ?
C13 C12 H12A 108.7 . . ?
C13 C12 H12B 108.7 . . ?
N1 C3 C4 113.15(19) . . ?
N1 C3 C2 122.4(2) . . ?
C2 C3 C4 124.3(2) . . ?
C19 C24 Ni1 116.57(15) . . ?
C23 C24 Ni1 126.43(17) . . ?
C23 C24 C19 116.88(19) . . ?
C19 C16 C17 113.03(18) . . ?
C19 C16 C15 103.62(17) . . ?
C19 C16 C18 109.40(17) . . ?
C15 C16 C17 112.74(19) . . ?
C18 C16 C17 108.64(18) . . ?
C18 C16 C15 109.28(18) . . ?
N3 C7 H7A 109.6 . . ?
N3 C7 H7B 109.6 . . ?
N3 C7 C6 110.3(2) . . ?
H7A C7 H7B 108.1 . . ?
C6 C7 H7A 109.6 . . ?
C6 C7 H7B 109.6 . . ?
C19 C20 H20 119.9 . . ?
C21 C20 C19 120.2(2) . . ?
C21 C20 H20 119.9 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
N1 C13 C12 117.88(19) . . ?
N1 C13 C14 120.4(2) . . ?
C14 C13 C12 121.4(2) . . ?
C2 C1 H1 120.4 . . ?
C2 C1 C14 119.2(2) . . ?
C14 C1 H1 120.4 . . ?
Ni1 C15 H15A 109.4 . . ?
Ni1 C15 H15B 109.4 . . ?
C16 C15 Ni1 111.19(14) . . ?
C16 C15 H15A 109.4 . . ?
C16 C15 H15B 109.4 . . ?
H15A C15 H15B 108.0 . . ?
N2 C6 C7 114.82(19) . . ?
N2 C6 H6A 108.6 . . ?
N2 C6 H6B 108.6 . . ?
C7 C6 H6A 108.6 . . ?
C7 C6 H6B 108.6 . . ?
H6A C6 H6B 107.5 . . ?
C24 C23 H23 119.3 . . ?
C22 C23 C24 121.5(2) . . ?
C22 C23 H23 119.3 . . ?
N2 C4 C3 109.02(18) . . ?
N2 C4 H4A 109.9 . . ?
N2 C4 H4B 109.9 . . ?
C3 C4 H4A 109.9 . . ?
C3 C4 H4B 109.9 . . ?
H4A C4 H4B 108.3 . . ?
C23 C22 H22 119.9 . . ?
C21 C22 C23 120.1(2) . . ?
C21 C22 H22 119.9 . . ?
C20 C21 H21 120.1 . . ?
C22 C21 C20 119.8(2) . . ?
C22 C21 H21 120.1 . . ?
C3 C2 H2 120.6 . . ?
C1 C2 C3 118.8(2) . . ?
C1 C2 H2 120.6 . . ?
N3 C8 H8A 109.5 . . ?
N3 C8 H8B 109.5 . . ?
N3 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N4 C10 H10A 109.1 . . ?
N4 C10 H10B 109.1 . . ?
N4 C10 C9 112.5(2) . . ?
H10A C10 H10B 107.8 . . ?
C9 C10 H10A 109.1 . . ?
C9 C10 H10B 109.1 . . ?
C16 C18 H18A 109.5 . . ?
C16 C18 H18B 109.5 . . ?
C16 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C13 C14 H14 120.1 . . ?
C1 C14 C13 119.9(2) . . ?
C1 C14 H14 120.1 . . ?
N3 C9 C10 110.2(2) . . ?
N3 C9 H9A 109.6 . . ?
N3 C9 H9B 109.6 . . ?
C10 C9 H9A 109.6 . . ?
C10 C9 H9B 109.6 . . ?
H9A C9 H9B 108.1 . . ?
N2 C5 H5A 109.5 . . ?
N2 C5 H5B 109.5 . . ?
N2 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
N4 C11 H11A 109.5 . . ?
N4 C11 H11B 109.5 . . ?
N4 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?

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
Ni1 N2 C6 C7 -55.8(2) . . . . ?
Ni1 N2 C4 C3 -52.68(19) . . . . ?
Ni1 N1 C3 C4 7.7(2) . . . . ?
Ni1 N1 C3 C2 -175.54(18) . . . . ?
Ni1 N1 C13 C12 -14.6(3) . . . . ?
Ni1 N1 C13 C14 171.77(17) . . . . ?
Ni1 C24 C23 C22 -177.10(17) . . . . ?
N4 C12 C13 N1 -103.8(2) . . . . ?
N4 C12 C13 C14 69.8(3) . . . . ?
N4 C10 C9 N3 -176.0(2) . . . . ?
N2 Ni1 C24 C19 -110.5(4) . . . . ?
N2 Ni1 C24 C23 65.3(5) . . . . ?
N1 Ni1 C24 C19 159.62(15) . . . . ?
N1 Ni1 C24 C23 -24.5(2) . . . . ?
N1 C3 C4 N2 32.8(3) . . . . ?
N1 C3 C2 C1 2.0(4) . . . . ?
N1 C13 C14 C1 5.4(4) . . . . ?
N3 C7 C6 N2 123.1(2) . . . . ?
C19 C24 C23 C22 -1.2(3) . . . . ?
C19 C16 C15 Ni1 -38.09(19) . . . . ?
C19 C20 C21 C22 0.3(3) . . . . ?
C12 N4 C10 C9 62.2(3) . . . . ?
C12 C13 C14 C1 -168.1(2) . . . . ?
C3 N1 C13 C12 166.2(2) . . . . ?
C3 N1 C13 C14 -7.4(3) . . . . ?
C24 C19 C16 C17 146.70(19) . . . . ?
C24 C19 C16 C15 24.3(2) . . . . ?
C24 C19 C16 C18 -92.1(2) . . . . ?
C24 C19 C20 C21 -2.2(3) . . . . ?
C24 C23 C22 C21 -0.6(3) . . . . ?
C16 C19 C24 Ni1 -0.7(2) . . . . ?
C16 C19 C24 C23 -176.96(18) . . . . ?
C16 C19 C20 C21 177.30(19) . . . . ?
C7 N3 C9 C10 133.4(2) . . . . ?
C20 C19 C24 Ni1 178.91(15) . . . . ?
C20 C19 C24 C23 2.6(3) . . . . ?
C20 C19 C16 C17 -32.9(3) . . . . ?
C20 C19 C16 C15 -155.2(2) . . . . ?
C20 C19 C16 C18 88.3(2) . . . . ?
C17 C16 C15 Ni1 -160.64(15) . . . . ?
C13 N1 C3 C4 -172.9(2) . . . . ?
C13 N1 C3 C2 3.8(3) . . . . ?
C15 Ni1 C24 C19 -17.89(15) . . . . ?
C15 Ni1 C24 C23 158.0(2) . . . . ?
C6 N2 C4 C3 68.2(2) . . . . ?
C23 C22 C21 C20 1.0(3) . . . . ?
C4 N2 C6 C7 -163.91(19) . . . . ?
C4 C3 C2 C1 178.3(2) . . . . ?
C2 C3 C4 N2 -143.9(2) . . . . ?
C2 C1 C14 C13 0.5(4) . . . . ?
C8 N3 C7 C6 153.4(2) . . . . ?
C8 N3 C9 C10 -98.0(2) . . . . ?
C10 N4 C12 C13 44.8(3) . . . . ?
C18 C16 C15 Ni1 78.45(19) . . . . ?
C14 C1 C2 C3 -4.0(4) . . . . ?
C9 N3 C7 C6 -79.6(2) . . . . ?
C5 N2 C6 C7 77.7(2) . . . . ?
C5 N2 C4 C3 -173.88(19) . . . . ?
C11 N4 C12 C13 -79.3(2) . . . . ?
C11 N4 C10 C9 -170.7(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_14_a
_database_code_depnum_ccdc_archive 'CCDC 2118412'
loop_
_audit_author_name
_audit_author_address
'Liviu Mirica'
;University of Illinois at Urbana Champaign
United States of America
;
_audit_update_record             
;
2021-10-29 deposited with the CCDC.	2022-01-13 downloaded from the CCDC.
;
_audit_creation_date             2020-01-28
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelxl_version_number           2014/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H36 N4 Ni, F6 P'
_chemical_formula_sum            'C24 H36 F6 N4 Ni P'
_chemical_formula_weight         584.25
_chemical_melting_point          ?
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'
F F 0.0171 0.0103 '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'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
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                   8.4822(2)
_cell_length_b                   10.1578(2)
_cell_length_c                   29.7277(6)
_cell_angle_alpha                90
_cell_angle_beta                 97.0100(10)
_cell_angle_gamma                90
_cell_volume                     2542.21(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    39171
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      28.276
_cell_measurement_theta_min      2.433
_shelx_estimated_absorpt_T_max   0.933
_shelx_estimated_absorpt_T_min   0.841
_exptl_absorpt_coefficient_mu    0.891
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6982
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1019 before and 0.0510 after correction. The Ratio of minimum to maximum transmission is 0.9363. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.526
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1220
_exptl_crystal_preparation       ?
_exptl_crystal_recrystallization_method 
'prepared from vapor diffusion of Et2O into concentrated solution of complex in MeCN'
_exptl_crystal_size_max          0.201
_exptl_crystal_size_mid          0.113
_exptl_crystal_size_min          0.079
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0351
_diffrn_reflns_av_unetI/netI     0.0149
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_number            83724
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.290
_diffrn_reflns_theta_min         2.120
_diffrn_ambient_temperature      100.0
_diffrn_detector                 'Bruker D8 Venture'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            'CPAD area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'kappa diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture_Mo'
_diffrn_measurement_method       'profile data from φ and ω scans'
_diffrn_radiation_monochromator  multi-mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_target            Mo
_diffrn_source_type              'Ius microfocus sealed tube'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5819
_reflns_number_total             6326
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.503
_refine_diff_density_min         -0.439
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     330
_refine_ls_number_reflns         6326
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0315
_refine_ls_R_factor_gt           0.0283
_refine_ls_restrained_S_all      1.039
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0291P)²+2.0054P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0691
_refine_ls_wR_factor_ref         0.0716
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C16(H16A,H16B), C17(H17A,H17B), C18(H18A,H18B), C19(H19A,H19B),
 C20(H20A,H20B), C21(H21A,H21B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C12(H12), C13(H13), C14(H14)
2.c Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C10(H10A,H10B,H10C), C22(H22A,H22B,H22C), C23(H23A,H23B,
 H23C), C24(H24A,H24B,H24C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Ni1 Ni 0.18949(2) 0.69504(2) 0.38972(2) 0.01487(5) Uani 1 1 d . . . . .
N1 N 0.30322(13) 0.70890(11) 0.33502(4) 0.0168(2) Uani 1 1 d . . . . .
C1 C 0.37092(15) 0.75034(13) 0.43212(4) 0.0171(2) Uani 1 1 d . . . . .
C2 C 0.09251(17) 0.68339(17) 0.44649(5) 0.0255(3) Uani 1 1 d . . . . .
H2A H 0.0001 0.7437 0.4438 0.031 Uiso 1 1 calc R . . . .
H2B H 0.0508 0.5929 0.4488 0.031 Uiso 1 1 calc R . . . .
N2 N 0.24610(15) 0.48167(12) 0.37834(4) 0.0239(3) Uani 1 1 d . . . . .
N3 N -0.02352(14) 0.64390(13) 0.34669(4) 0.0205(2) Uani 1 1 d . . . . .
C3 C 0.51460(17) 0.79188(15) 0.41818(5) 0.0224(3) Uani 1 1 d . . . . .
H3 H 0.5289 0.7868 0.3870 0.027 Uiso 1 1 calc R . . . .
C4 C 0.63692(18) 0.84050(17) 0.44924(5) 0.0266(3) Uani 1 1 d . . . . .
H4 H 0.7334 0.8687 0.4391 0.032 Uiso 1 1 calc R . . . .
N4 N 0.12079(15) 0.89931(12) 0.36581(4) 0.0214(2) Uani 1 1 d . . . . .
C5 C 0.61852(18) 0.84789(16) 0.49477(5) 0.0260(3) Uani 1 1 d . . . . .
H5 H 0.7028 0.8799 0.5159 0.031 Uiso 1 1 calc R . . . .
C6 C 0.47670(18) 0.80850(15) 0.50942(5) 0.0228(3) Uani 1 1 d . . . . .
H6 H 0.4634 0.8145 0.5406 0.027 Uiso 1 1 calc R . . . .
C7 C 0.35372(16) 0.76013(14) 0.47846(5) 0.0185(3) Uani 1 1 d . . . . .
C8 C 0.19681(18) 0.71492(17) 0.49165(5) 0.0260(3) Uani 1 1 d . . . . .
C9 C 0.2219(2) 0.5920(2) 0.52184(6) 0.0429(5) Uani 1 1 d . . . . .
H9A H 0.2768 0.5242 0.5062 0.064 Uiso 1 1 calc GR . . . .
H9B H 0.1187 0.5583 0.5282 0.064 Uiso 1 1 calc GR . . . .
H9C H 0.2863 0.6152 0.5504 0.064 Uiso 1 1 calc GR . . . .
C10 C 0.1182(2) 0.8220(2) 0.51799(6) 0.0395(5) Uani 1 1 d . . . . .
H10A H 0.1854 0.8406 0.5465 0.059 Uiso 1 1 calc GR . . . .
H10B H 0.0139 0.7912 0.5246 0.059 Uiso 1 1 calc GR . . . .
H10C H 0.1051 0.9024 0.4997 0.059 Uiso 1 1 calc GR . . . .
C11 C 0.31131(18) 0.82511(15) 0.31415(5) 0.0216(3) Uani 1 1 d . . . . .
C12 C 0.3922(2) 0.83904(19) 0.27655(5) 0.0319(4) Uani 1 1 d . . . . .
H12 H 0.3974 0.9221 0.2621 0.038 Uiso 1 1 calc R . . . .
C13 C 0.4651(2) 0.7298(2) 0.26056(5) 0.0353(4) Uani 1 1 d . . . . .
H13 H 0.5208 0.7370 0.2348 0.042 Uiso 1 1 calc R . . . .
C14 C 0.45657(18) 0.61021(19) 0.28209(5) 0.0303(4) Uani 1 1 d . . . . .
H14 H 0.5054 0.5342 0.2713 0.036 Uiso 1 1 calc R . . . .
C15 C 0.37497(16) 0.60281(15) 0.32001(5) 0.0215(3) Uani 1 1 d . . . . .
C16 C 0.37445(19) 0.48218(16) 0.34882(6) 0.0286(3) Uani 1 1 d . . . . .
H16A H 0.3627 0.4038 0.3289 0.034 Uiso 1 1 calc R . . . .
H16B H 0.4781 0.4752 0.3680 0.034 Uiso 1 1 calc R . . . .
C17 C 0.0983(2) 0.42487(16) 0.35457(6) 0.0307(3) Uani 1 1 d . . . . .
H17A H 0.0276 0.3982 0.3771 0.037 Uiso 1 1 calc R . . . .
H17B H 0.1244 0.3452 0.3378 0.037 Uiso 1 1 calc R . . . .
C18 C 0.01254(18) 0.52253(15) 0.32188(5) 0.0241(3) Uani 1 1 d . . . . .
H18A H 0.0797 0.5448 0.2980 0.029 Uiso 1 1 calc R . . . .
H18B H -0.0874 0.4831 0.3072 0.029 Uiso 1 1 calc R . . . .
C19 C -0.05621(17) 0.75572(16) 0.31455(5) 0.0234(3) Uani 1 1 d . . . . .
H19A H -0.1653 0.7479 0.2986 0.028 Uiso 1 1 calc R . . . .
H19B H 0.0190 0.7529 0.2916 0.028 Uiso 1 1 calc R . . . .
C20 C -0.03894(19) 0.88503(16) 0.33977(5) 0.0282(3) Uani 1 1 d . . . . .
H20A H -0.0572 0.9584 0.3178 0.034 Uiso 1 1 calc R . . . .
H20B H -0.1206 0.8905 0.3608 0.034 Uiso 1 1 calc R . . . .
C21 C 0.2405(2) 0.93960(15) 0.33666(5) 0.0264(3) Uani 1 1 d . . . . .
H21A H 0.3265 0.9882 0.3552 0.032 Uiso 1 1 calc R . . . .
H21B H 0.1907 1.0003 0.3130 0.032 Uiso 1 1 calc R . . . .
C22 C 0.2986(2) 0.40117(17) 0.41884(6) 0.0357(4) Uani 1 1 d . . . . .
H22A H 0.3920 0.4420 0.4360 0.054 Uiso 1 1 calc GR . . . .
H22B H 0.3260 0.3125 0.4094 0.054 Uiso 1 1 calc GR . . . .
H22C H 0.2127 0.3956 0.4380 0.054 Uiso 1 1 calc GR . . . .
C23 C -0.16806(18) 0.6184(2) 0.36894(6) 0.0340(4) Uani 1 1 d . . . . .
H23A H -0.1487 0.5439 0.3898 0.051 Uiso 1 1 calc GR . . . .
H23B H -0.2572 0.5977 0.3458 0.051 Uiso 1 1 calc GR . . . .
H23C H -0.1937 0.6968 0.3858 0.051 Uiso 1 1 calc GR . . . .
C24 C 0.1152(2) 0.99976(17) 0.40161(5) 0.0322(4) Uani 1 1 d . . . . .
H24A H 0.0345 0.9751 0.4210 0.048 Uiso 1 1 calc GR . . . .
H24B H 0.0883 1.0855 0.3876 0.048 Uiso 1 1 calc GR . . . .
H24C H 0.2192 1.0052 0.4199 0.048 Uiso 1 1 calc GR . . . .
F1 F 0.83559(13) 0.18805(10) 0.34088(4) 0.0456(3) Uani 1 1 d . . . . .
P1 P 0.65062(5) 0.17945(4) 0.32211(2) 0.02328(9) Uani 1 1 d . . . . .
F2 F 0.69787(14) 0.10576(11) 0.27827(3) 0.0392(2) Uani 1 1 d . . . . .
F3 F 0.46734(12) 0.17311(11) 0.30121(5) 0.0457(3) Uani 1 1 d . . . . .
F4 F 0.6062(2) 0.25126(17) 0.36618(4) 0.0780(6) Uani 1 1 d . . . . .
F5 F 0.63765(13) 0.03992(12) 0.34594(4) 0.0489(3) Uani 1 1 d . . . . .
F6 F 0.66168(13) 0.31950(10) 0.29765(4) 0.0420(3) 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
Ni1 N1 1.9944(11) . ?
Ni1 C1 1.9492(13) . ?
Ni1 C2 1.9693(14) . ?
Ni1 N2 2.2543(13) . ?
Ni1 N3 2.1463(12) . ?
Ni1 N4 2.2470(12) . ?
N1 C11 1.3391(18) . ?
N1 C15 1.3405(18) . ?
C1 C3 1.3995(19) . ?
C1 C7 1.4064(18) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C8 1.548(2) . ?
N2 C16 1.479(2) . ?
N2 C17 1.479(2) . ?
N2 C22 1.4786(19) . ?
N3 C18 1.4874(19) . ?
N3 C19 1.4884(19) . ?
N3 C23 1.4852(19) . ?
C3 H3 0.9500 . ?
C3 C4 1.393(2) . ?
C4 H4 0.9500 . ?
C4 C5 1.383(2) . ?
N4 C20 1.4833(19) . ?
N4 C21 1.471(2) . ?
N4 C24 1.4792(18) . ?
C5 H5 0.9500 . ?
C5 C6 1.387(2) . ?
C6 H6 0.9500 . ?
C6 C7 1.3936(19) . ?
C7 C8 1.504(2) . ?
C8 C9 1.537(2) . ?
C8 C10 1.539(2) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 C12 1.388(2) . ?
C11 C21 1.503(2) . ?
C12 H12 0.9500 . ?
C12 C13 1.383(3) . ?
C13 H13 0.9500 . ?
C13 C14 1.379(3) . ?
C14 H14 0.9500 . ?
C14 C15 1.395(2) . ?
C15 C16 1.495(2) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C17 C18 1.512(2) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C19 C20 1.511(2) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
F1 P1 1.6022(11) . ?
P1 F2 1.5957(10) . ?
P1 F3 1.6035(11) . ?
P1 F4 1.5846(12) . ?
P1 F5 1.5943(11) . ?
P1 F6 1.6055(11) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 Ni1 N2 79.19(5) . . ?
N1 Ni1 N3 89.25(5) . . ?
N1 Ni1 N4 79.02(5) . . ?
C1 Ni1 N1 94.86(5) . . ?
C1 Ni1 C2 80.93(6) . . ?
C1 Ni1 N2 102.02(5) . . ?
C1 Ni1 N3 174.85(5) . . ?
C1 Ni1 N4 95.29(5) . . ?
C2 Ni1 N1 175.74(5) . . ?
C2 Ni1 N2 100.94(6) . . ?
C2 Ni1 N3 94.99(5) . . ?
C2 Ni1 N4 101.96(6) . . ?
N3 Ni1 N2 81.78(5) . . ?
N3 Ni1 N4 82.42(5) . . ?
N4 Ni1 N2 153.14(4) . . ?
C11 N1 Ni1 119.81(9) . . ?
C11 N1 C15 120.23(12) . . ?
C15 N1 Ni1 119.93(10) . . ?
C3 C1 Ni1 122.86(10) . . ?
C3 C1 C7 117.84(12) . . ?
C7 C1 Ni1 119.06(10) . . ?
Ni1 C2 H2A 107.7 . . ?
Ni1 C2 H2B 107.7 . . ?
H2A C2 H2B 107.1 . . ?
C8 C2 Ni1 118.45(10) . . ?
C8 C2 H2A 107.7 . . ?
C8 C2 H2B 107.7 . . ?
C16 N2 Ni1 105.74(9) . . ?
C17 N2 Ni1 105.26(9) . . ?
C17 N2 C16 111.12(13) . . ?
C22 N2 Ni1 117.26(10) . . ?
C22 N2 C16 108.33(13) . . ?
C22 N2 C17 109.07(13) . . ?
C18 N3 Ni1 106.68(8) . . ?
C18 N3 C19 110.36(11) . . ?
C19 N3 Ni1 105.98(9) . . ?
C23 N3 Ni1 117.22(9) . . ?
C23 N3 C18 107.89(13) . . ?
C23 N3 C19 108.64(12) . . ?
C1 C3 H3 119.5 . . ?
C4 C3 C1 121.04(13) . . ?
C4 C3 H3 119.5 . . ?
C3 C4 H4 119.9 . . ?
C5 C4 C3 120.28(14) . . ?
C5 C4 H4 119.9 . . ?
C20 N4 Ni1 105.06(9) . . ?
C21 N4 Ni1 105.80(9) . . ?
C21 N4 C20 111.83(12) . . ?
C21 N4 C24 108.48(13) . . ?
C24 N4 Ni1 116.06(9) . . ?
C24 N4 C20 109.61(12) . . ?
C4 C5 H5 120.1 . . ?
C4 C5 C6 119.82(14) . . ?
C6 C5 H5 120.1 . . ?
C5 C6 H6 119.9 . . ?
C5 C6 C7 120.14(13) . . ?
C7 C6 H6 119.9 . . ?
C1 C7 C8 115.75(12) . . ?
C6 C7 C1 120.86(13) . . ?
C6 C7 C8 123.39(13) . . ?
C7 C8 C2 105.51(11) . . ?
C7 C8 C9 109.64(14) . . ?
C7 C8 C10 111.65(14) . . ?
C9 C8 C2 111.22(14) . . ?
C9 C8 C10 108.34(14) . . ?
C10 C8 C2 110.49(14) . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C8 C10 H10A 109.5 . . ?
C8 C10 H10B 109.5 . . ?
C8 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N1 C11 C12 121.41(15) . . ?
N1 C11 C21 115.47(12) . . ?
C12 C11 C21 122.90(14) . . ?
C11 C12 H12 120.6 . . ?
C13 C12 C11 118.72(16) . . ?
C13 C12 H12 120.6 . . ?
C12 C13 H13 120.1 . . ?
C14 C13 C12 119.77(15) . . ?
C14 C13 H13 120.1 . . ?
C13 C14 H14 120.6 . . ?
C13 C14 C15 118.81(15) . . ?
C15 C14 H14 120.6 . . ?
N1 C15 C14 121.05(15) . . ?
N1 C15 C16 115.78(13) . . ?
C14 C15 C16 122.92(14) . . ?
N2 C16 C15 113.35(12) . . ?
N2 C16 H16A 108.9 . . ?
N2 C16 H16B 108.9 . . ?
C15 C16 H16A 108.9 . . ?
C15 C16 H16B 108.9 . . ?
H16A C16 H16B 107.7 . . ?
N2 C17 H17A 109.4 . . ?
N2 C17 H17B 109.4 . . ?
N2 C17 C18 111.37(12) . . ?
H17A C17 H17B 108.0 . . ?
C18 C17 H17A 109.4 . . ?
C18 C17 H17B 109.4 . . ?
N3 C18 C17 109.70(12) . . ?
N3 C18 H18A 109.7 . . ?
N3 C18 H18B 109.7 . . ?
C17 C18 H18A 109.7 . . ?
C17 C18 H18B 109.7 . . ?
H18A C18 H18B 108.2 . . ?
N3 C19 H19A 109.6 . . ?
N3 C19 H19B 109.6 . . ?
N3 C19 C20 110.23(11) . . ?
H19A C19 H19B 108.1 . . ?
C20 C19 H19A 109.6 . . ?
C20 C19 H19B 109.6 . . ?
N4 C20 C19 111.79(12) . . ?
N4 C20 H20A 109.3 . . ?
N4 C20 H20B 109.3 . . ?
C19 C20 H20A 109.3 . . ?
C19 C20 H20B 109.3 . . ?
H20A C20 H20B 107.9 . . ?
N4 C21 C11 112.90(12) . . ?
N4 C21 H21A 109.0 . . ?
N4 C21 H21B 109.0 . . ?
C11 C21 H21A 109.0 . . ?
C11 C21 H21B 109.0 . . ?
H21A C21 H21B 107.8 . . ?
N2 C22 H22A 109.5 . . ?
N2 C22 H22B 109.5 . . ?
N2 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
N3 C23 H23A 109.5 . . ?
N3 C23 H23B 109.5 . . ?
N3 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
N4 C24 H24A 109.5 . . ?
N4 C24 H24B 109.5 . . ?
N4 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
F1 P1 F3 177.49(7) . . ?
F1 P1 F6 90.03(6) . . ?
F2 P1 F1 88.69(7) . . ?
F2 P1 F3 89.60(7) . . ?
F2 P1 F6 90.66(6) . . ?
F3 P1 F6 88.14(6) . . ?
F4 P1 F1 90.48(8) . . ?
F4 P1 F2 178.96(7) . . ?
F4 P1 F3 91.25(8) . . ?
F4 P1 F5 90.31(8) . . ?
F4 P1 F6 89.97(8) . . ?
F5 P1 F1 90.65(6) . . ?
F5 P1 F2 89.07(7) . . ?
F5 P1 F3 91.16(6) . . ?
F5 P1 F6 179.26(7) . . ?

_olex2_exptl_crystal_mounting_method 
;
was mounted using Paratone-N oil to a
Hampton Research 0.3 mm cryo-loop Hampton Research
with the (1 3 -2) scattering
planes roughly normal to the spindle axis
;
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_l18817
_database_code_depnum_ccdc_archive 'CCDC 2118413'
loop_
_audit_author_name
_audit_author_address
'Liviu Mirica'
;University of Illinois at Urbana Champaign
United States of America
;
_audit_update_record             
;
2021-10-29 deposited with the CCDC.	2022-01-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H24 Cl2 N4 Ni'
_chemical_formula_sum            'C14 H24 Cl2 N4 Ni'
_chemical_formula_weight         377.98

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'

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

_cell_length_a                   25.5261(8)
_cell_length_b                   7.5526(2)
_cell_length_c                   34.2402(12)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     6601.1(4)
_cell_formula_units_Z            16
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9682
_cell_measurement_theta_min      2.38
_cell_measurement_theta_max      31.04

_exptl_crystal_description       plate
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.521
_exptl_crystal_F_000             3168
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.541
_exptl_crystal_size_mid          0.294
_exptl_crystal_size_min          0.107
_exptl_absorpt_coefficient_mu    1.498
_shelx_estimated_absorpt_T_min   0.498
_shelx_estimated_absorpt_T_max   0.856
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4866
_exptl_absorpt_correction_T_max  0.5655
_exptl_absorpt_process_details   'SADABS V2016/2 (Bruker AXS Inc.)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_detector_area_resol_mean 8
_diffrn_reflns_number            121388
_diffrn_reflns_av_unetI/netI     0.0719
_diffrn_reflns_av_R_equivalents  0.0800
_diffrn_reflns_limit_h_min       -38
_diffrn_reflns_limit_h_max       38
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -51
_diffrn_reflns_limit_l_max       51
_diffrn_reflns_theta_min         1.189
_diffrn_reflns_theta_max         32.656
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             24015
_reflns_number_gt                18871
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.971
_reflns_Friedel_fraction_max     0.998
_reflns_Friedel_fraction_full    1.000

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    'SHELXT-2013 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
; 
 Refined as a 2-component inversion twin. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0304P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
; 
 Refined as an inversion twin. 
;
_refine_ls_abs_structure_Flack   0.394(10)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         24015
_refine_ls_number_parameters     770
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0671
_refine_ls_R_factor_gt           0.0447
_refine_ls_wR_factor_ref         0.0811
_refine_ls_wR_factor_gt          0.0741
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_restrained_S_all      1.012
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Ni1 Ni 0.51836(2) 0.40239(6) 0.56549(2) 0.00887(9) Uani 1 1 d . . . . .
Cl1 Cl 0.58515(4) 0.59711(12) 0.58441(3) 0.01465(19) Uani 1 1 d . . . . .
Cl2 Cl 0.50082(4) 0.57905(12) 0.50797(3) 0.01583(19) Uani 1 1 d . . . . .
N1 N 0.45949(12) 0.2435(4) 0.54754(10) 0.0112(6) Uani 1 1 d . . . . .
N2 N 0.45376(18) 0.4993(4) 0.60205(17) 0.0127(10) Uani 1 1 d . . . . .
N3 N 0.53132(13) 0.2284(4) 0.61609(10) 0.0114(7) Uani 1 1 d . . . . .
N4 N 0.56286(13) 0.1995(4) 0.53527(10) 0.0117(7) Uani 1 1 d . . . . .
C1 C 0.47027(15) 0.1072(5) 0.52418(13) 0.0125(8) Uani 1 1 d . . . . .
C2 C 0.4316(2) -0.0120(5) 0.5133(2) 0.0164(12) Uani 1 1 d . . . . .
H2 H 0.439613 -0.110394 0.497042 0.020 Uiso 1 1 calc R U . . .
C3 C 0.3813(2) 0.0160(5) 0.5266(2) 0.0196(12) Uani 1 1 d . . . . .
H3 H 0.354148 -0.063981 0.519521 0.024 Uiso 1 1 calc R U . . .
C4 C 0.37004(16) 0.1608(5) 0.55024(14) 0.0166(9) Uani 1 1 d . . . . .
H4 H 0.335427 0.181676 0.559337 0.020 Uiso 1 1 calc R U . . .
C5 C 0.41080(15) 0.2743(5) 0.56023(13) 0.0132(8) Uani 1 1 d . . . . .
C6 C 0.40420(16) 0.4435(5) 0.58274(15) 0.0169(9) Uani 1 1 d . . . . .
H6A H 0.392459 0.538187 0.564762 0.020 Uiso 1 1 calc R U . . .
H6B H 0.376718 0.427110 0.602818 0.020 Uiso 1 1 calc R U . . .
C7 C 0.45969(16) 0.4136(5) 0.64033(13) 0.0154(8) Uani 1 1 d . . . . .
H7A H 0.425303 0.411084 0.653692 0.019 Uiso 1 1 calc R U . . .
H7B H 0.484050 0.484119 0.656585 0.019 Uiso 1 1 calc R U . . .
C8 C 0.48048(15) 0.2255(5) 0.63672(13) 0.0136(8) Uani 1 1 d . . . . .
H8A H 0.484987 0.173227 0.663027 0.016 Uiso 1 1 calc R U . . .
H8B H 0.455173 0.151742 0.622049 0.016 Uiso 1 1 calc R U . . .
C9 C 0.54561(16) 0.0563(5) 0.59864(13) 0.0145(8) Uani 1 1 d . . . . .
H9A H 0.513832 -0.002517 0.588326 0.017 Uiso 1 1 calc R U . . .
H9B H 0.561135 -0.021293 0.618868 0.017 Uiso 1 1 calc R U . . .
C10 C 0.58472(16) 0.0840(5) 0.56581(15) 0.0170(8) Uani 1 1 d . . . . .
H10A H 0.617038 0.138136 0.576440 0.020 Uiso 1 1 calc R U . . .
H10B H 0.594123 -0.031888 0.554278 0.020 Uiso 1 1 calc R U . . .
C11 C 0.52587(16) 0.1004(5) 0.50992(14) 0.0176(9) Uani 1 1 d . . . . .
H11A H 0.537205 -0.024758 0.508479 0.021 Uiso 1 1 calc R U . . .
H11B H 0.527380 0.150147 0.483187 0.021 Uiso 1 1 calc R U . . .
C12 C 0.45358(17) 0.6933(5) 0.60659(15) 0.0195(9) Uani 1 1 d . . . . .
H12A H 0.451635 0.749147 0.580805 0.029 Uiso 1 1 calc R U . . .
H12B H 0.485796 0.730746 0.619785 0.029 Uiso 1 1 calc R U . . .
H12C H 0.423189 0.728919 0.622216 0.029 Uiso 1 1 calc R U . . .
C13 C 0.57265(16) 0.2818(5) 0.64366(13) 0.0165(9) Uani 1 1 d . . . . .
H13A H 0.562815 0.393673 0.656193 0.025 Uiso 1 1 calc R U . . .
H13B H 0.605710 0.297427 0.629526 0.025 Uiso 1 1 calc R U . . .
H13C H 0.576936 0.189995 0.663626 0.025 Uiso 1 1 calc R U . . .
C14 C 0.60627(16) 0.2731(5) 0.51115(14) 0.0175(9) Uani 1 1 d . . . . .
H14A H 0.629515 0.343949 0.527709 0.026 Uiso 1 1 calc R U . . .
H14B H 0.591678 0.347903 0.490452 0.026 Uiso 1 1 calc R U . . .
H14C H 0.626176 0.175697 0.499408 0.026 Uiso 1 1 calc R U . . .
Ni1A Ni 0.23350(2) 0.09150(6) 0.43572(2) 0.00937(10) Uani 1 1 d . . . . .
Cl1A Cl 0.16648(4) -0.10203(12) 0.41648(3) 0.01591(19) Uani 1 1 d . . . . .
Cl2A Cl 0.25121(4) -0.08640(12) 0.49310(3) 0.01621(19) Uani 1 1 d . . . . .
N1A N 0.29267(12) 0.2484(4) 0.45339(11) 0.0114(6) Uani 1 1 d . . . . .
N2A N 0.18963(13) 0.2955(4) 0.46649(11) 0.0125(7) Uani 1 1 d . . . . .
N3A N 0.22016(13) 0.2672(4) 0.38574(10) 0.0120(7) Uani 1 1 d . . . . .
N4A N 0.29792(18) -0.0064(4) 0.39950(16) 0.0125(10) Uani 1 1 d . . . . .
C1A C 0.34155(15) 0.2186(5) 0.44068(13) 0.0135(8) Uani 1 1 d . . . . .
C2A C 0.38222(16) 0.3312(5) 0.45016(14) 0.0182(9) Uani 1 1 d . . . . .
H2A H 0.416562 0.310640 0.440486 0.022 Uiso 1 1 calc R U . . .
C3A C 0.3718(2) 0.4755(5) 0.4742(2) 0.0192(12) Uani 1 1 d . . . . .
H3A H 0.399109 0.554874 0.481172 0.023 Uiso 1 1 calc R U . . .
C4A C 0.3216(2) 0.5028(5) 0.4878(2) 0.0179(13) Uani 1 1 d . . . . .
H4A H 0.313860 0.600472 0.504258 0.021 Uiso 1 1 calc R U . . .
C5A C 0.28261(15) 0.3848(5) 0.47688(13) 0.0132(8) Uani 1 1 d . . . . .
C6A C 0.22738(16) 0.3919(5) 0.49160(14) 0.0162(8) Uani 1 1 d . . . . .
H6AA H 0.226234 0.340848 0.518213 0.019 Uiso 1 1 calc R U . . .
H6AB H 0.216370 0.517318 0.493487 0.019 Uiso 1 1 calc R U . . .
C7A C 0.16837(16) 0.4134(5) 0.43589(14) 0.0159(8) Uani 1 1 d . . . . .
H7AA H 0.159491 0.529528 0.447548 0.019 Uiso 1 1 calc R U . . .
H7AB H 0.135802 0.361352 0.425171 0.019 Uiso 1 1 calc R U . . .
C8A C 0.20717(17) 0.4398(5) 0.40341(14) 0.0162(9) Uani 1 1 d . . . . .
H8AA H 0.192095 0.519202 0.383332 0.019 Uiso 1 1 calc R U . . .
H8AB H 0.239352 0.495804 0.413780 0.019 Uiso 1 1 calc R U . . .
C9A C 0.27075(16) 0.2679(5) 0.36468(13) 0.0174(9) Uani 1 1 d . . . . .
H9AA H 0.296477 0.340600 0.379202 0.021 Uiso 1 1 calc R U . . .
H9AB H 0.266004 0.320906 0.338481 0.021 Uiso 1 1 calc R U . . .
C10A C 0.29116(17) 0.0806(5) 0.36060(13) 0.0178(9) Uani 1 1 d . . . . .
H10C H 0.266348 0.010452 0.344645 0.021 Uiso 1 1 calc R U . . .
H10D H 0.325249 0.082796 0.346822 0.021 Uiso 1 1 calc R U . . .
C11A C 0.34764(17) 0.0502(5) 0.41734(15) 0.0166(9) Uani 1 1 d . . . . .
H11C H 0.373974 0.069175 0.396537 0.020 Uiso 1 1 calc R U . . .
H11D H 0.360717 -0.044945 0.434674 0.020 Uiso 1 1 calc R U . . .
C12A C 0.14673(16) 0.2244(5) 0.49066(14) 0.0185(9) Uani 1 1 d . . . . .
H12D H 0.161206 0.145292 0.510615 0.028 Uiso 1 1 calc R U . . .
H12E H 0.122284 0.158317 0.474087 0.028 Uiso 1 1 calc R U . . .
H12F H 0.128162 0.322328 0.503353 0.028 Uiso 1 1 calc R U . . .
C13A C 0.17850(17) 0.2190(5) 0.35802(14) 0.0190(9) Uani 1 1 d . . . . .
H13D H 0.145062 0.209777 0.371937 0.028 Uiso 1 1 calc R U . . .
H13E H 0.186860 0.104901 0.345892 0.028 Uiso 1 1 calc R U . . .
H13F H 0.175815 0.310192 0.337757 0.028 Uiso 1 1 calc R U . . .
C14A C 0.29819(18) -0.2015(5) 0.39448(15) 0.0196(9) Uani 1 1 d . . . . .
H14D H 0.265923 -0.238555 0.381304 0.029 Uiso 1 1 calc R U . . .
H14E H 0.300314 -0.258553 0.420134 0.029 Uiso 1 1 calc R U . . .
H14F H 0.328515 -0.236185 0.378683 0.029 Uiso 1 1 calc R U . . .
Ni1B Ni 0.77020(2) 0.65647(6) 0.69790(2) 0.00999(10) Uani 1 1 d . . . . .
Cl1B Cl 0.77367(4) 0.85875(12) 0.75052(3) 0.0180(2) Uani 1 1 d . . . . .
Cl2B Cl 0.83644(4) 0.82066(12) 0.66214(3) 0.01495(19) Uani 1 1 d . . . . .
N1B N 0.77197(16) 0.4888(4) 0.65183(14) 0.0103(8) Uani 1 1 d . . . . .
N2B N 0.70380(12) 0.7518(4) 0.66425(11) 0.0125(7) Uani 1 1 d . . . . .
N3B N 0.71010(17) 0.4924(4) 0.72636(15) 0.0128(9) Uani 1 1 d . . . . .
N4B N 0.82237(13) 0.4506(4) 0.71996(11) 0.0115(6) Uani 1 1 d . . . . .
C1B C 0.80250(15) 0.3454(5) 0.65237(12) 0.0111(7) Uani 1 1 d . . . . .
C2B C 0.80304(16) 0.2267(5) 0.62149(13) 0.0151(8) Uani 1 1 d . . . . .
H2B H 0.825656 0.126809 0.621803 0.018 Uiso 1 1 calc R U . . .
C3B C 0.76977(18) 0.2571(5) 0.59008(14) 0.0194(9) Uani 1 1 d . . . . .
H3B H 0.768279 0.175355 0.569011 0.023 Uiso 1 1 calc R U . . .
C4B C 0.73862(17) 0.4085(5) 0.58979(14) 0.0181(9) Uani 1 1 d . . . . .
H4B H 0.715752 0.431640 0.568499 0.022 Uiso 1 1 calc R U . . .
C5B C 0.7414(2) 0.5234(5) 0.62056(19) 0.0146(11) Uani 1 1 d . . . . .
C6B C 0.71393(16) 0.6998(5) 0.62342(13) 0.0142(8) Uani 1 1 d . . . . .
H6BA H 0.735762 0.791626 0.610731 0.017 Uiso 1 1 calc R U . . .
H6BB H 0.680242 0.693372 0.609162 0.017 Uiso 1 1 calc R U . . .
C7B C 0.65622(15) 0.6595(5) 0.67968(14) 0.0153(8) Uani 1 1 d . . . . .
H7BA H 0.630272 0.646948 0.658376 0.018 Uiso 1 1 calc R U . . .
H7BB H 0.640211 0.732983 0.700441 0.018 Uiso 1 1 calc R U . . .
C8B C 0.66875(18) 0.4777(5) 0.69613(17) 0.0130(9) Uani 1 1 d . . . . .
H8BA H 0.636780 0.425331 0.707729 0.016 Uiso 1 1 calc R U . . .
H8BB H 0.680842 0.398890 0.674860 0.016 Uiso 1 1 calc R U . . .
C9B C 0.73671(16) 0.3221(5) 0.73450(13) 0.0151(8) Uani 1 1 d . . . . .
H9BA H 0.738745 0.250979 0.710261 0.018 Uiso 1 1 calc R U . . .
H9BB H 0.716399 0.254091 0.754037 0.018 Uiso 1 1 calc R U . . .
C10B C 0.79121(16) 0.3569(5) 0.74984(13) 0.0163(8) Uani 1 1 d . . . . .
H10E H 0.789189 0.429605 0.773848 0.020 Uiso 1 1 calc R U . . .
H10F H 0.808369 0.243273 0.756519 0.020 Uiso 1 1 calc R U . . .
C11B C 0.83717(16) 0.3287(5) 0.68790(13) 0.0144(8) Uani 1 1 d . . . . .
H11E H 0.835475 0.205351 0.697625 0.017 Uiso 1 1 calc R U . . .
H11F H 0.873860 0.352830 0.680181 0.017 Uiso 1 1 calc R U . . .
C12B C 0.69565(17) 0.9458(5) 0.66596(15) 0.0186(9) Uani 1 1 d . . . . .
H12G H 0.727570 1.006376 0.657355 0.028 Uiso 1 1 calc R U . . .
H12H H 0.687487 0.980711 0.692845 0.028 Uiso 1 1 calc R U . . .
H12I H 0.666483 0.978586 0.648810 0.028 Uiso 1 1 calc R U . . .
C13B C 0.68673(18) 0.5599(6) 0.76244(14) 0.0194(9) Uani 1 1 d . . . . .
H13G H 0.672063 0.677846 0.757730 0.029 Uiso 1 1 calc R U . . .
H13H H 0.713677 0.567252 0.782769 0.029 Uiso 1 1 calc R U . . .
H13I H 0.658817 0.479663 0.770998 0.029 Uiso 1 1 calc R U . . .
C14B C 0.86968(19) 0.5302(5) 0.73775(17) 0.0154(10) Uani 1 1 d . . . . .
H14G H 0.859554 0.600552 0.760581 0.023 Uiso 1 1 calc R U . . .
H14H H 0.887069 0.606611 0.718605 0.023 Uiso 1 1 calc R U . . .
H14I H 0.893740 0.435953 0.745858 0.023 Uiso 1 1 calc R U . . .
Ni1C Ni 0.48123(2) 0.13270(6) 0.30171(2) 0.01070(10) Uani 1 1 d . . . . .
Cl1C Cl 0.47659(4) 0.33157(13) 0.24845(3) 0.0209(2) Uani 1 1 d . . . . .
Cl2C Cl 0.41425(4) 0.29544(12) 0.33641(3) 0.0165(2) Uani 1 1 d . . . . .
N1C N 0.48055(16) -0.0344(4) 0.34807(14) 0.0124(8) Uani 1 1 d . . . . .
N2C N 0.43086(13) -0.0820(4) 0.27978(11) 0.0139(7) Uani 1 1 d . . . . .
N3C N 0.54339(17) -0.0251(4) 0.27465(15) 0.0126(9) Uani 1 1 d . . . . .
N4C N 0.54688(12) 0.2369(4) 0.33583(11) 0.0134(7) Uani 1 1 d . . . . .
C1C C 0.5103(2) 0.0037(5) 0.37859(19) 0.0132(11) Uani 1 1 d . . . . .
C2C C 0.51279(17) -0.1085(5) 0.41082(13) 0.0182(9) Uani 1 1 d . . . . .
H2C H 0.535096 -0.082329 0.432266 0.022 Uiso 1 1 calc R U . . .
C3C C 0.48191(18) -0.2592(5) 0.41080(14) 0.0209(9) Uani 1 1 d . . . . .
H3C H 0.482935 -0.338256 0.432364 0.025 Uiso 1 1 calc R U . . .
C4C C 0.44956(17) -0.2944(5) 0.37935(14) 0.0179(9) Uani 1 1 d . . . . .
H4C H 0.427496 -0.395721 0.379278 0.022 Uiso 1 1 calc R U . . .
C5C C 0.45005(15) -0.1789(5) 0.34799(13) 0.0129(8) Uani 1 1 d . . . . .
C6C C 0.41639(15) -0.2018(5) 0.31236(13) 0.0158(8) Uani 1 1 d . . . . .
H6CA H 0.419138 -0.325886 0.303280 0.019 Uiso 1 1 calc R U . . .
H6CB H 0.379402 -0.179875 0.319588 0.019 Uiso 1 1 calc R U . . .
C7C C 0.46483(16) -0.1762(5) 0.25135(13) 0.0156(8) Uani 1 1 d . . . . .
H7CA H 0.466837 -0.106997 0.226836 0.019 Uiso 1 1 calc R U . . .
H7CB H 0.449303 -0.293002 0.245162 0.019 Uiso 1 1 calc R U . . .
C8C C 0.51946(16) -0.2019(5) 0.26770(14) 0.0152(8) Uani 1 1 d . . . . .
H8CA H 0.517704 -0.269030 0.292498 0.018 Uiso 1 1 calc R U . . .
H8CB H 0.541095 -0.270018 0.248982 0.018 Uiso 1 1 calc R U . . .
C9C C 0.58556(18) -0.0319(5) 0.30415(18) 0.0157(10) Uani 1 1 d . . . . .
H9CA H 0.618064 -0.077927 0.292089 0.019 Uiso 1 1 calc R U . . .
H9CB H 0.575389 -0.112745 0.325603 0.019 Uiso 1 1 calc R U . . .
C10C C 0.59530(15) 0.1528(5) 0.32038(13) 0.0156(8) Uani 1 1 d . . . . .
H10G H 0.621579 0.145354 0.341584 0.019 Uiso 1 1 calc R U . . .
H10H H 0.610028 0.228393 0.299466 0.019 Uiso 1 1 calc R U . . .
C11C C 0.53733(17) 0.1813(5) 0.37674(13) 0.0163(8) Uani 1 1 d . . . . .
H11G H 0.515342 0.271126 0.389956 0.020 Uiso 1 1 calc R U . . .
H11H H 0.571154 0.174330 0.390796 0.020 Uiso 1 1 calc R U . . .
C12C C 0.3842(2) -0.0181(5) 0.25968(19) 0.0195(11) Uani 1 1 d . . . . .
H12J H 0.361162 0.041685 0.278412 0.029 Uiso 1 1 calc R U . . .
H12K H 0.365556 -0.118423 0.247974 0.029 Uiso 1 1 calc R U . . .
H12L H 0.394428 0.065352 0.239142 0.029 Uiso 1 1 calc R U . . .
C13C C 0.56552(18) 0.0390(6) 0.23726(15) 0.0178(9) Uani 1 1 d . . . . .
H13J H 0.537721 0.044906 0.217567 0.027 Uiso 1 1 calc R U . . .
H13K H 0.592932 -0.042547 0.228439 0.027 Uiso 1 1 calc R U . . .
H13L H 0.580568 0.157176 0.241038 0.027 Uiso 1 1 calc R U . . .
C14C C 0.55233(17) 0.4301(5) 0.33485(15) 0.0190(9) Uani 1 1 d . . . . .
H14J H 0.557538 0.469080 0.307821 0.028 Uiso 1 1 calc R U . . .
H14K H 0.582560 0.465523 0.350668 0.028 Uiso 1 1 calc R U . . .
H14L H 0.520533 0.484945 0.345387 0.028 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ni1 N1 2.019(3) . ?
Ni1 N4 2.170(3) . ?
Ni1 N2 2.196(5) . ?
Ni1 N3 2.199(3) . ?
Ni1 Cl1 2.3429(10) . ?
Ni1 Cl2 2.4208(11) . ?
N1 C1 1.333(5) . ?
N1 C5 1.337(5) . ?
N2 C7 1.470(7) . ?
N2 C12 1.473(5) . ?
N2 C6 1.488(6) . ?
N3 C13 1.472(5) . ?
N3 C9 1.477(5) . ?
N3 C8 1.478(5) . ?
N4 C10 1.472(6) . ?
N4 C11 1.485(5) . ?
N4 C14 1.489(5) . ?
C1 C2 1.387(6) . ?
C1 C11 1.502(6) . ?
C2 C3 1.380(8) . ?
C2 H2 0.9500 . ?
C3 C4 1.391(7) . ?
C3 H3 0.9500 . ?
C4 C5 1.391(5) . ?
C4 H4 0.9500 . ?
C5 C6 1.502(6) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.521(5) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.518(6) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
Ni1A N1A 2.013(3) . ?
Ni1A N2A 2.177(3) . ?
Ni1A N4A 2.188(5) . ?
Ni1A N3A 2.192(3) . ?
Ni1A Cl1A 2.3447(10) . ?
Ni1A Cl2A 2.4225(11) . ?
N1A C5A 1.332(5) . ?
N1A C1A 1.340(5) . ?
N2A C12A 1.474(5) . ?
N2A C7A 1.478(6) . ?
N2A C6A 1.483(5) . ?
N3A C13A 1.471(5) . ?
N3A C8A 1.475(5) . ?
N3A C9A 1.479(5) . ?
N4A C11A 1.472(6) . ?
N4A C14A 1.483(5) . ?
N4A C10A 1.495(7) . ?
C1A C2A 1.381(5) . ?
C1A C11A 1.510(6) . ?
C2A C3A 1.391(7) . ?
C2A H2A 0.9500 . ?
C3A C4A 1.379(8) . ?
C3A H3A 0.9500 . ?
C4A C5A 1.387(6) . ?
C4A H4A 0.9500 . ?
C5A C6A 1.498(6) . ?
C6A H6AA 0.9900 . ?
C6A H6AB 0.9900 . ?
C7A C8A 1.502(6) . ?
C7A H7AA 0.9900 . ?
C7A H7AB 0.9900 . ?
C8A H8AA 0.9900 . ?
C8A H8AB 0.9900 . ?
C9A C10A 1.514(6) . ?
C9A H9AA 0.9900 . ?
C9A H9AB 0.9900 . ?
C10A H10C 0.9900 . ?
C10A H10D 0.9900 . ?
C11A H11C 0.9900 . ?
C11A H11D 0.9900 . ?
C12A H12D 0.9800 . ?
C12A H12E 0.9800 . ?
C12A H12F 0.9800 . ?
C13A H13D 0.9800 . ?
C13A H13E 0.9800 . ?
C13A H13F 0.9800 . ?
C14A H14D 0.9800 . ?
C14A H14E 0.9800 . ?
C14A H14F 0.9800 . ?
Ni1B N1B 2.023(4) . ?
Ni1B N2B 2.172(3) . ?
Ni1B N4B 2.182(3) . ?
Ni1B N3B 2.200(4) . ?
Ni1B Cl1B 2.3638(11) . ?
Ni1B Cl2B 2.4281(11) . ?
N1B C1B 1.335(5) . ?
N1B C5B 1.350(7) . ?
N2B C6B 1.475(6) . ?
N2B C12B 1.481(5) . ?
N2B C7B 1.497(5) . ?
N3B C13B 1.464(6) . ?
N3B C9B 1.481(5) . ?
N3B C8B 1.482(7) . ?
N4B C10B 1.477(5) . ?
N4B C14B 1.480(6) . ?
N4B C11B 1.482(5) . ?
C1B C2B 1.386(6) . ?
C1B C11B 1.510(6) . ?
C2B C3B 1.390(6) . ?
C2B H2B 0.9500 . ?
C3B C4B 1.393(6) . ?
C3B H3B 0.9500 . ?
C4B C5B 1.367(7) . ?
C4B H4B 0.9500 . ?
C5B C6B 1.509(6) . ?
C6B H6BA 0.9900 . ?
C6B H6BB 0.9900 . ?
C7B C8B 1.518(6) . ?
C7B H7BA 0.9900 . ?
C7B H7BB 0.9900 . ?
C8B H8BA 0.9900 . ?
C8B H8BB 0.9900 . ?
C9B C10B 1.510(6) . ?
C9B H9BA 0.9900 . ?
C9B H9BB 0.9900 . ?
C10B H10E 0.9900 . ?
C10B H10F 0.9900 . ?
C11B H11E 0.9900 . ?
C11B H11F 0.9900 . ?
C12B H12G 0.9800 . ?
C12B H12H 0.9800 . ?
C12B H12I 0.9800 . ?
C13B H13G 0.9800 . ?
C13B H13H 0.9800 . ?
C13B H13I 0.9800 . ?
C14B H14G 0.9800 . ?
C14B H14H 0.9800 . ?
C14B H14I 0.9800 . ?
Ni1C N1C 2.028(4) . ?
Ni1C N4C 2.190(3) . ?
Ni1C N3C 2.190(4) . ?
Ni1C N2C 2.202(3) . ?
Ni1C Cl1C 2.3653(12) . ?
Ni1C Cl2C 2.4177(11) . ?
N1C C1C 1.324(7) . ?
N1C C5C 1.341(5) . ?
N2C C12C 1.458(6) . ?
N2C C6C 1.483(5) . ?
N2C C7C 1.485(5) . ?
N3C C9C 1.477(7) . ?
N3C C13C 1.481(7) . ?
N3C C8C 1.488(5) . ?
N4C C14C 1.466(5) . ?
N4C C11C 1.482(6) . ?
N4C C10C 1.487(5) . ?
C1C C2C 1.393(7) . ?
C1C C11C 1.509(6) . ?
C2C C3C 1.384(6) . ?
C2C H2C 0.9500 . ?
C3C C4C 1.383(6) . ?
C3C H3C 0.9500 . ?
C4C C5C 1.384(6) . ?
C4C H4C 0.9500 . ?
C5C C6C 1.502(6) . ?
C6C H6CA 0.9900 . ?
C6C H6CB 0.9900 . ?
C7C C8C 1.515(6) . ?
C7C H7CA 0.9900 . ?
C7C H7CB 0.9900 . ?
C8C H8CA 0.9900 . ?
C8C H8CB 0.9900 . ?
C9C C10C 1.522(6) . ?
C9C H9CA 0.9900 . ?
C9C H9CB 0.9900 . ?
C10C H10G 0.9900 . ?
C10C H10H 0.9900 . ?
C11C H11G 0.9900 . ?
C11C H11H 0.9900 . ?
C12C H12J 0.9800 . ?
C12C H12K 0.9800 . ?
C12C H12L 0.9800 . ?
C13C H13J 0.9800 . ?
C13C H13K 0.9800 . ?
C13C H13L 0.9800 . ?
C14C H14J 0.9800 . ?
C14C H14K 0.9800 . ?
C14C H14L 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 Ni1 N4 79.91(13) . . ?
N1 Ni1 N2 79.20(15) . . ?
N4 Ni1 N2 154.19(12) . . ?
N1 Ni1 N3 89.82(13) . . ?
N4 Ni1 N3 82.83(13) . . ?
N2 Ni1 N3 82.12(15) . . ?
N1 Ni1 Cl1 177.33(10) . . ?
N4 Ni1 Cl1 101.20(9) . . ?
N2 Ni1 Cl1 100.35(11) . . ?
N3 Ni1 Cl1 92.73(9) . . ?
N1 Ni1 Cl2 86.68(10) . . ?
N4 Ni1 Cl2 95.62(10) . . ?
N2 Ni1 Cl2 98.12(13) . . ?
N3 Ni1 Cl2 176.37(9) . . ?
Cl1 Ni1 Cl2 90.78(4) . . ?
C1 N1 C5 121.4(3) . . ?
C1 N1 Ni1 119.2(3) . . ?
C5 N1 Ni1 119.3(3) . . ?
C7 N2 C12 110.1(4) . . ?
C7 N2 C6 111.1(4) . . ?
C12 N2 C6 109.0(4) . . ?
C7 N2 Ni1 106.5(3) . . ?
C12 N2 Ni1 113.2(3) . . ?
C6 N2 Ni1 106.9(3) . . ?
C13 N3 C9 108.9(3) . . ?
C13 N3 C8 109.1(3) . . ?
C9 N3 C8 113.4(3) . . ?
C13 N3 Ni1 116.7(2) . . ?
C9 N3 Ni1 104.1(3) . . ?
C8 N3 Ni1 104.7(2) . . ?
C10 N4 C11 111.0(3) . . ?
C10 N4 C14 109.5(3) . . ?
C11 N4 C14 109.7(3) . . ?
C10 N4 Ni1 106.1(3) . . ?
C11 N4 Ni1 107.6(2) . . ?
C14 N4 Ni1 113.0(2) . . ?
N1 C1 C2 121.1(4) . . ?
N1 C1 C11 114.6(3) . . ?
C2 C1 C11 124.2(4) . . ?
C3 C2 C1 118.3(5) . . ?
C3 C2 H2 120.8 . . ?
C1 C2 H2 120.8 . . ?
C2 C3 C4 120.3(4) . . ?
C2 C3 H3 119.8 . . ?
C4 C3 H3 119.8 . . ?
C5 C4 C3 118.3(4) . . ?
C5 C4 H4 120.9 . . ?
C3 C4 H4 120.9 . . ?
N1 C5 C4 120.6(4) . . ?
N1 C5 C6 114.8(3) . . ?
C4 C5 C6 124.5(4) . . ?
N2 C6 C5 111.9(3) . . ?
N2 C6 H6A 109.2 . . ?
C5 C6 H6A 109.2 . . ?
N2 C6 H6B 109.2 . . ?
C5 C6 H6B 109.2 . . ?
H6A C6 H6B 107.9 . . ?
N2 C7 C8 112.0(4) . . ?
N2 C7 H7A 109.2 . . ?
C8 C7 H7A 109.2 . . ?
N2 C7 H7B 109.2 . . ?
C8 C7 H7B 109.2 . . ?
H7A C7 H7B 107.9 . . ?
N3 C8 C7 109.3(3) . . ?
N3 C8 H8A 109.8 . . ?
C7 C8 H8A 109.8 . . ?
N3 C8 H8B 109.8 . . ?
C7 C8 H8B 109.8 . . ?
H8A C8 H8B 108.3 . . ?
N3 C9 C10 109.9(3) . . ?
N3 C9 H9A 109.7 . . ?
C10 C9 H9A 109.7 . . ?
N3 C9 H9B 109.7 . . ?
C10 C9 H9B 109.7 . . ?
H9A C9 H9B 108.2 . . ?
N4 C10 C9 111.0(3) . . ?
N4 C10 H10A 109.4 . . ?
C9 C10 H10A 109.4 . . ?
N4 C10 H10B 109.4 . . ?
C9 C10 H10B 109.4 . . ?
H10A C10 H10B 108.0 . . ?
N4 C11 C1 113.2(3) . . ?
N4 C11 H11A 108.9 . . ?
C1 C11 H11A 108.9 . . ?
N4 C11 H11B 108.9 . . ?
C1 C11 H11B 108.9 . . ?
H11A C11 H11B 107.8 . . ?
N2 C12 H12A 109.5 . . ?
N2 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
N2 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N3 C13 H13A 109.5 . . ?
N3 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
N3 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N4 C14 H14A 109.5 . . ?
N4 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
N4 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N1A Ni1A N2A 79.86(13) . . ?
N1A Ni1A N4A 78.77(15) . . ?
N2A Ni1A N4A 154.16(12) . . ?
N1A Ni1A N3A 89.70(13) . . ?
N2A Ni1A N3A 82.50(13) . . ?
N4A Ni1A N3A 83.03(15) . . ?
N1A Ni1A Cl1A 177.43(10) . . ?
N2A Ni1A Cl1A 101.65(9) . . ?
N4A Ni1A Cl1A 100.28(11) . . ?
N3A Ni1A Cl1A 92.55(9) . . ?
N1A Ni1A Cl2A 86.72(10) . . ?
N2A Ni1A Cl2A 95.52(10) . . ?
N4A Ni1A Cl2A 97.59(13) . . ?
N3A Ni1A Cl2A 176.18(9) . . ?
Cl1A Ni1A Cl2A 91.05(4) . . ?
C5A N1A C1A 120.3(3) . . ?
C5A N1A Ni1A 119.5(3) . . ?
C1A N1A Ni1A 120.1(3) . . ?
C12A N2A C7A 110.2(3) . . ?
C12A N2A C6A 109.6(3) . . ?
C7A N2A C6A 110.7(3) . . ?
C12A N2A Ni1A 113.3(2) . . ?
C7A N2A Ni1A 105.8(3) . . ?
C6A N2A Ni1A 107.1(2) . . ?
C13A N3A C8A 108.7(3) . . ?
C13A N3A C9A 108.5(3) . . ?
C8A N3A C9A 113.2(3) . . ?
C13A N3A Ni1A 117.8(2) . . ?
C8A N3A Ni1A 104.5(3) . . ?
C9A N3A Ni1A 104.3(2) . . ?
C11A N4A C14A 109.4(4) . . ?
C11A N4A C10A 110.0(4) . . ?
C14A N4A C10A 109.5(4) . . ?
C11A N4A Ni1A 108.3(3) . . ?
C14A N4A Ni1A 113.9(3) . . ?
C10A N4A Ni1A 105.6(3) . . ?
N1A C1A C2A 121.3(4) . . ?
N1A C1A C11A 114.1(3) . . ?
C2A C1A C11A 124.5(4) . . ?
C1A C2A C3A 118.6(4) . . ?
C1A C2A H2A 120.7 . . ?
C3A C2A H2A 120.7 . . ?
C4A C3A C2A 119.6(4) . . ?
C4A C3A H3A 120.2 . . ?
C2A C3A H3A 120.2 . . ?
C3A C4A C5A 118.7(5) . . ?
C3A C4A H4A 120.6 . . ?
C5A C4A H4A 120.6 . . ?
N1A C5A C4A 121.4(4) . . ?
N1A C5A C6A 114.3(3) . . ?
C4A C5A C6A 124.2(4) . . ?
N2A C6A C5A 113.5(3) . . ?
N2A C6A H6AA 108.9 . . ?
C5A C6A H6AA 108.9 . . ?
N2A C6A H6AB 108.9 . . ?
C5A C6A H6AB 108.9 . . ?
H6AA C6A H6AB 107.7 . . ?
N2A C7A C8A 111.3(3) . . ?
N2A C7A H7AA 109.4 . . ?
C8A C7A H7AA 109.4 . . ?
N2A C7A H7AB 109.4 . . ?
C8A C7A H7AB 109.4 . . ?
H7AA C7A H7AB 108.0 . . ?
N3A C8A C7A 109.5(3) . . ?
N3A C8A H8AA 109.8 . . ?
C7A C8A H8AA 109.8 . . ?
N3A C8A H8AB 109.8 . . ?
C7A C8A H8AB 109.8 . . ?
H8AA C8A H8AB 108.2 . . ?
N3A C9A C10A 110.0(3) . . ?
N3A C9A H9AA 109.7 . . ?
C10A C9A H9AA 109.7 . . ?
N3A C9A H9AB 109.7 . . ?
C10A C9A H9AB 109.7 . . ?
H9AA C9A H9AB 108.2 . . ?
N4A C10A C9A 111.6(4) . . ?
N4A C10A H10C 109.3 . . ?
C9A C10A H10C 109.3 . . ?
N4A C10A H10D 109.3 . . ?
C9A C10A H10D 109.3 . . ?
H10C C10A H10D 108.0 . . ?
N4A C11A C1A 112.1(3) . . ?
N4A C11A H11C 109.2 . . ?
C1A C11A H11C 109.2 . . ?
N4A C11A H11D 109.2 . . ?
C1A C11A H11D 109.2 . . ?
H11C C11A H11D 107.9 . . ?
N2A C12A H12D 109.5 . . ?
N2A C12A H12E 109.5 . . ?
H12D C12A H12E 109.5 . . ?
N2A C12A H12F 109.5 . . ?
H12D C12A H12F 109.5 . . ?
H12E C12A H12F 109.5 . . ?
N3A C13A H13D 109.5 . . ?
N3A C13A H13E 109.5 . . ?
H13D C13A H13E 109.5 . . ?
N3A C13A H13F 109.5 . . ?
H13D C13A H13F 109.5 . . ?
H13E C13A H13F 109.5 . . ?
N4A C14A H14D 109.5 . . ?
N4A C14A H14E 109.5 . . ?
H14D C14A H14E 109.5 . . ?
N4A C14A H14F 109.5 . . ?
H14D C14A H14F 109.5 . . ?
H14E C14A H14F 109.5 . . ?
N1B Ni1B N2B 79.12(15) . . ?
N1B Ni1B N4B 79.07(15) . . ?
N2B Ni1B N4B 153.63(12) . . ?
N1B Ni1B N3B 90.48(16) . . ?
N2B Ni1B N3B 82.96(15) . . ?
N4B Ni1B N3B 82.58(14) . . ?
N1B Ni1B Cl1B 176.25(12) . . ?
N2B Ni1B Cl1B 102.66(10) . . ?
N4B Ni1B Cl1B 100.01(10) . . ?
N3B Ni1B Cl1B 93.02(12) . . ?
N1B Ni1B Cl2B 84.89(12) . . ?
N2B Ni1B Cl2B 96.12(9) . . ?
N4B Ni1B Cl2B 96.52(9) . . ?
N3B Ni1B Cl2B 175.37(12) . . ?
Cl1B Ni1B Cl2B 91.62(4) . . ?
C1B N1B C5B 120.4(4) . . ?
C1B N1B Ni1B 120.7(3) . . ?
C5B N1B Ni1B 119.0(3) . . ?
C6B N2B C12B 109.0(3) . . ?
C6B N2B C7B 110.7(3) . . ?
C12B N2B C7B 109.4(3) . . ?
C6B N2B Ni1B 106.1(2) . . ?
C12B N2B Ni1B 114.6(3) . . ?
C7B N2B Ni1B 107.0(2) . . ?
C13B N3B C9B 109.3(4) . . ?
C13B N3B C8B 109.0(4) . . ?
C9B N3B C8B 113.1(3) . . ?
C13B N3B Ni1B 117.5(3) . . ?
C9B N3B Ni1B 104.6(3) . . ?
C8B N3B Ni1B 103.3(3) . . ?
C10B N4B C14B 110.4(4) . . ?
C10B N4B C11B 110.6(3) . . ?
C14B N4B C11B 110.4(3) . . ?
C10B N4B Ni1B 104.6(2) . . ?
C14B N4B Ni1B 110.6(2) . . ?
C11B N4B Ni1B 110.0(2) . . ?
N1B C1B C2B 121.3(4) . . ?
N1B C1B C11B 114.9(4) . . ?
C2B C1B C11B 123.7(3) . . ?
C1B C2B C3B 118.5(4) . . ?
C1B C2B H2B 120.7 . . ?
C3B C2B H2B 120.7 . . ?
C2B C3B C4B 119.3(4) . . ?
C2B C3B H3B 120.3 . . ?
C4B C3B H3B 120.3 . . ?
C5B C4B C3B 119.1(4) . . ?
C5B C4B H4B 120.5 . . ?
C3B C4B H4B 120.5 . . ?
N1B C5B C4B 121.2(4) . . ?
N1B C5B C6B 112.8(4) . . ?
C4B C5B C6B 125.9(5) . . ?
N2B C6B C5B 112.2(4) . . ?
N2B C6B H6BA 109.2 . . ?
C5B C6B H6BA 109.2 . . ?
N2B C6B H6BB 109.2 . . ?
C5B C6B H6BB 109.2 . . ?
H6BA C6B H6BB 107.9 . . ?
N2B C7B C8B 112.4(3) . . ?
N2B C7B H7BA 109.1 . . ?
C8B C7B H7BA 109.1 . . ?
N2B C7B H7BB 109.1 . . ?
C8B C7B H7BB 109.1 . . ?
H7BA C7B H7BB 107.9 . . ?
N3B C8B C7B 110.0(3) . . ?
N3B C8B H8BA 109.7 . . ?
C7B C8B H8BA 109.7 . . ?
N3B C8B H8BB 109.7 . . ?
C7B C8B H8BB 109.7 . . ?
H8BA C8B H8BB 108.2 . . ?
N3B C9B C10B 109.7(3) . . ?
N3B C9B H9BA 109.7 . . ?
C10B C9B H9BA 109.7 . . ?
N3B C9B H9BB 109.7 . . ?
C10B C9B H9BB 109.7 . . ?
H9BA C9B H9BB 108.2 . . ?
N4B C10B C9B 109.8(3) . . ?
N4B C10B H10E 109.7 . . ?
C9B C10B H10E 109.7 . . ?
N4B C10B H10F 109.7 . . ?
C9B C10B H10F 109.7 . . ?
H10E C10B H10F 108.2 . . ?
N4B C11B C1B 113.3(3) . . ?
N4B C11B H11E 108.9 . . ?
C1B C11B H11E 108.9 . . ?
N4B C11B H11F 108.9 . . ?
C1B C11B H11F 108.9 . . ?
H11E C11B H11F 107.7 . . ?
N2B C12B H12G 109.5 . . ?
N2B C12B H12H 109.5 . . ?
H12G C12B H12H 109.5 . . ?
N2B C12B H12I 109.5 . . ?
H12G C12B H12I 109.5 . . ?
H12H C12B H12I 109.5 . . ?
N3B C13B H13G 109.5 . . ?
N3B C13B H13H 109.5 . . ?
H13G C13B H13H 109.5 . . ?
N3B C13B H13I 109.5 . . ?
H13G C13B H13I 109.5 . . ?
H13H C13B H13I 109.5 . . ?
N4B C14B H14G 109.5 . . ?
N4B C14B H14H 109.5 . . ?
H14G C14B H14H 109.5 . . ?
N4B C14B H14I 109.5 . . ?
H14G C14B H14I 109.5 . . ?
H14H C14B H14I 109.5 . . ?
N1C Ni1C N4C 79.19(15) . . ?
N1C Ni1C N3C 89.93(16) . . ?
N4C Ni1C N3C 82.35(15) . . ?
N1C Ni1C N2C 78.67(15) . . ?
N4C Ni1C N2C 153.36(12) . . ?
N3C Ni1C N2C 82.99(14) . . ?
N1C Ni1C Cl1C 176.49(12) . . ?
N4C Ni1C Cl1C 102.79(10) . . ?
N3C Ni1C Cl1C 93.19(12) . . ?
N2C Ni1C Cl1C 100.12(10) . . ?
N1C Ni1C Cl2C 85.73(11) . . ?
N4C Ni1C Cl2C 95.52(9) . . ?
N3C Ni1C Cl2C 175.46(13) . . ?
N2C Ni1C Cl2C 97.42(9) . . ?
Cl1C Ni1C Cl2C 91.18(4) . . ?
C1C N1C C5C 120.8(4) . . ?
C1C N1C Ni1C 118.5(3) . . ?
C5C N1C Ni1C 120.7(3) . . ?
C12C N2C C6C 110.7(4) . . ?
C12C N2C C7C 109.0(4) . . ?
C6C N2C C7C 110.3(3) . . ?
C12C N2C Ni1C 113.2(2) . . ?
C6C N2C Ni1C 109.8(3) . . ?
C7C N2C Ni1C 103.6(2) . . ?
C9C N3C C13C 108.9(4) . . ?
C9C N3C C8C 112.2(3) . . ?
C13C N3C C8C 108.2(4) . . ?
C9C N3C Ni1C 104.9(3) . . ?
C13C N3C Ni1C 117.7(3) . . ?
C8C N3C Ni1C 105.0(3) . . ?
C14C N4C C11C 108.6(3) . . ?
C14C N4C C10C 109.8(3) . . ?
C11C N4C C10C 110.6(3) . . ?
C14C N4C Ni1C 114.7(3) . . ?
C11C N4C Ni1C 106.0(2) . . ?
C10C N4C Ni1C 107.0(2) . . ?
N1C C1C C2C 121.3(4) . . ?
N1C C1C C11C 115.0(4) . . ?
C2C C1C C11C 123.6(5) . . ?
C3C C2C C1C 118.3(4) . . ?
C3C C2C H2C 120.9 . . ?
C1C C2C H2C 120.9 . . ?
C4C C3C C2C 119.9(4) . . ?
C4C C3C H3C 120.0 . . ?
C2C C3C H3C 120.0 . . ?
C3C C4C C5C 118.5(4) . . ?
C3C C4C H4C 120.7 . . ?
C5C C4C H4C 120.7 . . ?
N1C C5C C4C 121.1(4) . . ?
N1C C5C C6C 115.3(4) . . ?
C4C C5C C6C 123.6(4) . . ?
N2C C6C C5C 113.5(3) . . ?
N2C C6C H6CA 108.9 . . ?
C5C C6C H6CA 108.9 . . ?
N2C C6C H6CB 108.9 . . ?
C5C C6C H6CB 108.9 . . ?
H6CA C6C H6CB 107.7 . . ?
N2C C7C C8C 110.9(4) . . ?
N2C C7C H7CA 109.5 . . ?
C8C C7C H7CA 109.5 . . ?
N2C C7C H7CB 109.5 . . ?
C8C C7C H7CB 109.5 . . ?
H7CA C7C H7CB 108.0 . . ?
N3C C8C C7C 108.8(3) . . ?
N3C C8C H8CA 109.9 . . ?
C7C C8C H8CA 109.9 . . ?
N3C C8C H8CB 109.9 . . ?
C7C C8C H8CB 109.9 . . ?
H8CA C8C H8CB 108.3 . . ?
N3C C9C C10C 109.7(3) . . ?
N3C C9C H9CA 109.7 . . ?
C10C C9C H9CA 109.7 . . ?
N3C C9C H9CB 109.7 . . ?
C10C C9C H9CB 109.7 . . ?
H9CA C9C H9CB 108.2 . . ?
N4C C10C C9C 112.7(3) . . ?
N4C C10C H10G 109.1 . . ?
C9C C10C H10G 109.1 . . ?
N4C C10C H10H 109.1 . . ?
C9C C10C H10H 109.1 . . ?
H10G C10C H10H 107.8 . . ?
N4C C11C C1C 111.5(4) . . ?
N4C C11C H11G 109.3 . . ?
C1C C11C H11G 109.3 . . ?
N4C C11C H11H 109.3 . . ?
C1C C11C H11H 109.3 . . ?
H11G C11C H11H 108.0 . . ?
N2C C12C H12J 109.5 . . ?
N2C C12C H12K 109.5 . . ?
H12J C12C H12K 109.5 . . ?
N2C C12C H12L 109.5 . . ?
H12J C12C H12L 109.5 . . ?
H12K C12C H12L 109.5 . . ?
N3C C13C H13J 109.5 . . ?
N3C C13C H13K 109.5 . . ?
H13J C13C H13K 109.5 . . ?
N3C C13C H13L 109.5 . . ?
H13J C13C H13L 109.5 . . ?
H13K C13C H13L 109.5 . . ?
N4C C14C H14J 109.5 . . ?
N4C C14C H14K 109.5 . . ?
H14J C14C H14K 109.5 . . ?
N4C C14C H14L 109.5 . . ?
H14J C14C H14L 109.5 . . ?
H14K C14C H14L 109.5 . . ?

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
C5 N1 C1 C2 -2.3(6) . . . . ?
Ni1 N1 C1 C2 175.7(4) . . . . ?
C5 N1 C1 C11 175.1(4) . . . . ?
Ni1 N1 C1 C11 -6.9(5) . . . . ?
N1 C1 C2 C3 1.3(8) . . . . ?
C11 C1 C2 C3 -175.9(5) . . . . ?
C1 C2 C3 C4 0.1(9) . . . . ?
C2 C3 C4 C5 -0.5(8) . . . . ?
C1 N1 C5 C4 1.9(6) . . . . ?
Ni1 N1 C5 C4 -176.1(3) . . . . ?
C1 N1 C5 C6 -173.8(4) . . . . ?
Ni1 N1 C5 C6 8.2(5) . . . . ?
C3 C4 C5 N1 -0.5(7) . . . . ?
C3 C4 C5 C6 174.8(5) . . . . ?
C7 N2 C6 C5 -85.8(5) . . . . ?
C12 N2 C6 C5 152.6(4) . . . . ?
Ni1 N2 C6 C5 30.0(4) . . . . ?
N1 C5 C6 N2 -26.6(6) . . . . ?
C4 C5 C6 N2 157.9(4) . . . . ?
C12 N2 C7 C8 -158.4(4) . . . . ?
C6 N2 C7 C8 80.8(4) . . . . ?
Ni1 N2 C7 C8 -35.3(4) . . . . ?
C13 N3 C8 C7 79.3(4) . . . . ?
C9 N3 C8 C7 -159.2(4) . . . . ?
Ni1 N3 C8 C7 -46.3(4) . . . . ?
N2 C7 C8 N3 57.8(5) . . . . ?
C13 N3 C9 C10 -80.7(4) . . . . ?
C8 N3 C9 C10 157.7(4) . . . . ?
Ni1 N3 C9 C10 44.5(4) . . . . ?
C11 N4 C10 C9 -77.9(4) . . . . ?
C14 N4 C10 C9 160.9(3) . . . . ?
Ni1 N4 C10 C9 38.7(4) . . . . ?
N3 C9 C10 N4 -59.1(5) . . . . ?
C10 N4 C11 C1 90.4(4) . . . . ?
C14 N4 C11 C1 -148.5(3) . . . . ?
Ni1 N4 C11 C1 -25.3(4) . . . . ?
N1 C1 C11 N4 22.4(5) . . . . ?
C2 C1 C11 N4 -160.3(4) . . . . ?
C5A N1A C1A C2A -2.6(6) . . . . ?
Ni1A N1A C1A C2A 175.5(3) . . . . ?
C5A N1A C1A C11A 174.7(4) . . . . ?
Ni1A N1A C1A C11A -7.2(5) . . . . ?
N1A C1A C2A C3A 1.6(7) . . . . ?
C11A C1A C2A C3A -175.5(5) . . . . ?
C1A C2A C3A C4A -0.1(8) . . . . ?
C2A C3A C4A C5A -0.2(9) . . . . ?
C1A N1A C5A C4A 2.3(6) . . . . ?
Ni1A N1A C5A C4A -175.9(4) . . . . ?
C1A N1A C5A C6A -174.7(4) . . . . ?
Ni1A N1A C5A C6A 7.2(5) . . . . ?
C3A C4A C5A N1A -0.8(8) . . . . ?
C3A C4A C5A C6A 175.8(5) . . . . ?
C12A N2A C6A C5A 149.1(3) . . . . ?
C7A N2A C6A C5A -89.2(4) . . . . ?
Ni1A N2A C6A C5A 25.7(4) . . . . ?
N1A C5A C6A N2A -23.0(5) . . . . ?
C4A C5A C6A N2A 160.2(4) . . . . ?
C12A N2A C7A C8A -161.3(3) . . . . ?
C6A N2A C7A C8A 77.2(4) . . . . ?
Ni1A N2A C7A C8A -38.5(4) . . . . ?
C13A N3A C8A C7A 81.0(4) . . . . ?
C9A N3A C8A C7A -158.3(4) . . . . ?
Ni1A N3A C8A C7A -45.5(4) . . . . ?
N2A C7A C8A N3A 59.5(4) . . . . ?
C13A N3A C9A C10A -80.3(4) . . . . ?
C8A N3A C9A C10A 159.0(4) . . . . ?
Ni1A N3A C9A C10A 46.1(4) . . . . ?
C11A N4A C10A C9A -80.9(4) . . . . ?
C14A N4A C10A C9A 158.9(4) . . . . ?
Ni1A N4A C10A C9A 35.8(4) . . . . ?
N3A C9A C10A N4A -58.2(5) . . . . ?
C14A N4A C11A C1A -152.2(4) . . . . ?
C10A N4A C11A C1A 87.5(5) . . . . ?
Ni1A N4A C11A C1A -27.6(4) . . . . ?
N1A C1A C11A N4A 24.0(6) . . . . ?
C2A C1A C11A N4A -158.7(4) . . . . ?
C5B N1B C1B C2B -1.3(6) . . . . ?
Ni1B N1B C1B C2B 178.2(3) . . . . ?
C5B N1B C1B C11B 176.3(4) . . . . ?
Ni1B N1B C1B C11B -4.3(5) . . . . ?
N1B C1B C2B C3B -1.9(6) . . . . ?
C11B C1B C2B C3B -179.2(4) . . . . ?
C1B C2B C3B C4B 2.6(6) . . . . ?
C2B C3B C4B C5B -0.3(6) . . . . ?
C1B N1B C5B C4B 3.7(7) . . . . ?
Ni1B N1B C5B C4B -175.7(4) . . . . ?
C1B N1B C5B C6B -174.2(4) . . . . ?
Ni1B N1B C5B C6B 6.4(6) . . . . ?
C3B C4B C5B N1B -2.9(7) . . . . ?
C3B C4B C5B C6B 174.7(4) . . . . ?
C12B N2B C6B C5B 159.2(3) . . . . ?
C7B N2B C6B C5B -80.4(4) . . . . ?
Ni1B N2B C6B C5B 35.3(4) . . . . ?
N1B C5B C6B N2B -29.1(5) . . . . ?
C4B C5B C6B N2B 153.1(5) . . . . ?
C6B N2B C7B C8B 86.0(4) . . . . ?
C12B N2B C7B C8B -153.9(4) . . . . ?
Ni1B N2B C7B C8B -29.2(4) . . . . ?
C13B N3B C8B C7B 77.1(5) . . . . ?
C9B N3B C8B C7B -161.1(4) . . . . ?
Ni1B N3B C8B C7B -48.6(4) . . . . ?
N2B C7B C8B N3B 55.2(5) . . . . ?
C13B N3B C9B C10B -84.2(4) . . . . ?
C8B N3B C9B C10B 154.2(4) . . . . ?
Ni1B N3B C9B C10B 42.5(4) . . . . ?
C14B N4B C10B C9B 163.9(3) . . . . ?
C11B N4B C10B C9B -73.5(4) . . . . ?
Ni1B N4B C10B C9B 44.9(4) . . . . ?
N3B C9B C10B N4B -62.2(5) . . . . ?
C10B N4B C11B C1B 99.6(4) . . . . ?
C14B N4B C11B C1B -137.8(3) . . . . ?
Ni1B N4B C11B C1B -15.5(4) . . . . ?
N1B C1B C11B N4B 13.6(5) . . . . ?
C2B C1B C11B N4B -169.0(4) . . . . ?
C5C N1C C1C C2C 2.9(7) . . . . ?
Ni1C N1C C1C C2C -178.0(3) . . . . ?
C5C N1C C1C C11C -172.7(4) . . . . ?
Ni1C N1C C1C C11C 6.4(6) . . . . ?
N1C C1C C2C C3C -2.0(7) . . . . ?
C11C C1C C2C C3C 173.2(4) . . . . ?
C1C C2C C3C C4C -0.2(7) . . . . ?
C2C C3C C4C C5C 1.7(6) . . . . ?
C1C N1C C5C C4C -1.4(6) . . . . ?
Ni1C N1C C5C C4C 179.5(3) . . . . ?
C1C N1C C5C C6C 177.2(4) . . . . ?
Ni1C N1C C5C C6C -1.9(5) . . . . ?
C3C C4C C5C N1C -0.9(6) . . . . ?
C3C C4C C5C C6C -179.4(4) . . . . ?
C12C N2C C6C C5C -141.5(4) . . . . ?
C7C N2C C6C C5C 97.7(4) . . . . ?
Ni1C N2C C6C C5C -15.8(4) . . . . ?
N1C C5C C6C N2C 12.4(5) . . . . ?
C4C C5C C6C N2C -169.1(4) . . . . ?
C12C N2C C7C C8C 164.9(3) . . . . ?
C6C N2C C7C C8C -73.4(4) . . . . ?
Ni1C N2C C7C C8C 44.0(3) . . . . ?
C9C N3C C8C C7C 156.9(4) . . . . ?
C13C N3C C8C C7C -82.9(4) . . . . ?
Ni1C N3C C8C C7C 43.5(4) . . . . ?
N2C C7C C8C N3C -62.4(5) . . . . ?
C13C N3C C9C C10C 79.9(5) . . . . ?
C8C N3C C9C C10C -160.3(4) . . . . ?
Ni1C N3C C9C C10C -46.9(4) . . . . ?
C14C N4C C10C C9C -155.3(4) . . . . ?
C11C N4C C10C C9C 84.9(4) . . . . ?
Ni1C N4C C10C C9C -30.2(4) . . . . ?
N3C C9C C10C N4C 54.3(6) . . . . ?
C14C N4C C11C C1C 157.0(4) . . . . ?
C10C N4C C11C C1C -82.5(4) . . . . ?
Ni1C N4C C11C C1C 33.2(4) . . . . ?
N1C C1C C11C N4C -28.0(6) . . . . ?
C2C C1C C11C N4C 156.5(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
#C2 H2 Cl2  0.95 2.84 3.563(5) 133.3 1_545 
#C6 H6B Cl2B  0.99 2.95 3.790(5) 143.6 3_465 
#C7 H7A Cl2B  0.99 2.88 3.686(4) 139.2 3_465 
#C14 H14A Cl1  0.98 2.95 3.546(4) 120.2 . 
#C14 H14B Cl2  0.98 2.96 3.549(4) 119.4 . 
#C4A H4A Cl2A  0.95 2.88 3.590(5) 132.4 1_565 
#C7A H7AA Cl1A  0.99 2.98 3.720(4) 132.0 1_565 
#C11A H11C Cl2C  0.99 2.87 3.742(5) 147.9 . 
#C12A H12D Cl2A  0.98 2.95 3.554(4) 120.9 . 
#C14B H14G Cl1B  0.98 2.95 3.515(5) 117.4 . 
#C7C H7CB Cl1C  0.99 2.92 3.731(4) 139.6 1_545 
C10A H10D Cl2C 0.99 2.81 3.632(4) 141.5 .
C2B H2B Cl2B 0.95 2.71 3.474(4) 138.2 1_545
C6B H6BB Cl1 0.99 2.67 3.632(4) 163.5 .
C7B H7BA Cl1 0.99 2.81 3.762(5) 162.2 .
C8B H8BB N1B 0.99 2.55 3.041(7) 110.6 .
C14B H14H Cl2B 0.98 2.83 3.498(5) 125.9 .
C4C H4C Cl2C 0.95 2.78 3.545(4) 138.6 1_545
C10C H10G Cl1A 0.99 2.83 3.778(5) 161.1 3
C11C H11H Cl1A 0.99 2.64 3.616(4) 167.2 3
#C12C H12L Cl1C  0.98 2.92 3.562(5) 123.8 . 

_refine_diff_density_max         0.549
_refine_diff_density_min         -0.660
_refine_diff_density_rms         0.094

