# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_Compound_4
_database_code_depnum_ccdc_archive 'CCDC 2017693'
loop_
_audit_author_name
_audit_author_address
'Udo Radius'
;University Wuerzburg
Germany
;
_audit_update_record             
;
2020-07-20 deposited with the CCDC.	2020-10-06 downloaded from the CCDC.
;


_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C47 H48 F5 N5 Ni'
_chemical_formula_sum            'C47 H48 F5 N5 Ni'
_chemical_formula_weight         836.61

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-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                   20.0292(16)
_cell_length_b                   18.4196(14)
_cell_length_c                   22.4625(16)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     8287.1(11)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    8254
_cell_measurement_theta_min      2.21
_cell_measurement_theta_max      26.42

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.341
_exptl_crystal_F_000             3504
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.217
_exptl_crystal_size_mid          0.202
_exptl_crystal_size_min          0.202
_exptl_absorpt_coefficient_mu    0.531
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   'multi scan'
_exptl_absorpt_correction_T_min  0.4053
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_process_details   'Sadabs 2014/4 (Bruker 2014)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   rotating-anode
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            48652
_diffrn_reflns_av_unetI/netI     0.0639
_diffrn_reflns_av_R_equivalents  0.0849
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         1.754
_diffrn_reflns_theta_max         26.784
_diffrn_reflns_theta_full        26.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             8820
_reflns_number_gt                5766
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0764P)²+5.8232P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         8820
_refine_ls_number_parameters     535
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0968
_refine_ls_R_factor_gt           0.0500
_refine_ls_wR_factor_ref         0.1541
_refine_ls_wR_factor_gt          0.1240
_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
Ni1 Ni 0.38341(2) 0.59336(2) 0.27689(2) 0.01611(12) Uani 1 1 d . . . . .
C1_1 C 0.46232(14) 0.53778(16) 0.27543(13) 0.0190(6) Uani 1 1 d . . . . .
F1_1 F 0.47662(9) 0.54227(10) 0.17127(8) 0.0291(4) Uani 1 1 d . . . . .
N1_1 N 0.57662(15) 0.44468(17) 0.27510(15) 0.0390(8) Uani 1 1 d . . . . .
C2_1 C 0.49632(15) 0.51766(18) 0.22479(14) 0.0247(7) Uani 1 1 d . . . . .
F2_1 F 0.58141(10) 0.45307(12) 0.17508(10) 0.0441(6) Uani 1 1 d . . . . .
C3_1 C 0.55122(16) 0.47236(19) 0.22601(16) 0.0303(8) Uani 1 1 d . . . . .
F3_1 F 0.57138(12) 0.43634(13) 0.37501(11) 0.0578(7) Uani 1 1 d . . . . .
C4_1 C 0.54578(19) 0.4643(2) 0.32414(17) 0.0378(9) Uani 1 1 d . . . . .
F4_1 F 0.46502(11) 0.52207(12) 0.38046(9) 0.0418(5) Uani 1 1 d . . . . .
C5_1 C 0.49087(16) 0.50880(18) 0.32665(15) 0.0269(7) Uani 1 1 d . . . . .
F1_2 F 0.30402(8) 0.64559(10) 0.27888(7) 0.0240(4) Uani 1 1 d . . . . .
C1_3 C 0.43044(14) 0.67773(16) 0.30450(12) 0.0175(6) Uani 1 1 d . . . . .
N1_3 N 0.42414(12) 0.71539(14) 0.35681(11) 0.0199(5) Uani 1 1 d . . . . .
C2_3 C 0.46516(16) 0.77555(18) 0.35735(15) 0.0276(7) Uani 1 1 d . . . . .
H2_3 H 0.4691 0.8099 0.3887 0.033 Uiso 1 1 calc R U . . .
N2_3 N 0.47651(12) 0.71646(13) 0.27396(10) 0.0182(5) Uani 1 1 d . . . . .
C3_3 C 0.49828(16) 0.77682(17) 0.30571(14) 0.0266(7) Uani 1 1 d . . . . .
H3_3 H 0.5302 0.8118 0.2932 0.032 Uiso 1 1 calc R U . . .
C4_3 C 0.49726(15) 0.70413(16) 0.21313(13) 0.0186(6) Uani 1 1 d . . . . .
C5_3 C 0.56140(15) 0.67848(17) 0.20253(13) 0.0202(6) Uani 1 1 d . . . . .
C6_3 C 0.58133(16) 0.67031(17) 0.14356(13) 0.0234(7) Uani 1 1 d . . . . .
H6_3 H 0.6251 0.6532 0.1352 0.028 Uiso 1 1 calc R U . . .
C7_3 C 0.53871(17) 0.68668(17) 0.09658(14) 0.0250(7) Uani 1 1 d . . . . .
C8_3 C 0.47538(16) 0.71288(18) 0.10936(14) 0.0248(7) Uani 1 1 d . . . . .
H8_3 H 0.4462 0.7243 0.0773 0.030 Uiso 1 1 calc R U . . .
C9_3 C 0.45302(15) 0.72301(17) 0.16739(13) 0.0210(7) Uani 1 1 d . . . . .
C10_3 C 0.60934(16) 0.66091(18) 0.25233(14) 0.0257(7) Uani 1 1 d . . . . .
H10A_3 H 0.6477 0.6343 0.2363 0.038 Uiso 1 1 calc R U . . .
H10B_3 H 0.5867 0.6310 0.2822 0.038 Uiso 1 1 calc R U . . .
H10C_3 H 0.6248 0.7061 0.2708 0.038 Uiso 1 1 calc R U . . .
C11_3 C 0.5613(2) 0.6755(2) 0.03301(14) 0.0384(9) Uani 1 1 d . . . . .
H11A_3 H 0.5253 0.6525 0.0102 0.058 Uiso 1 1 calc R U . . .
H11B_3 H 0.6008 0.6442 0.0325 0.058 Uiso 1 1 calc R U . . .
H11C_3 H 0.5723 0.7226 0.0152 0.058 Uiso 1 1 calc R U . . .
C12_3 C 0.38542(15) 0.75487(19) 0.18006(15) 0.0269(7) Uani 1 1 d . . . . .
H12A_3 H 0.3623 0.7645 0.1424 0.040 Uiso 1 1 calc R U . . .
H12B_3 H 0.3907 0.8004 0.2022 0.040 Uiso 1 1 calc R U . . .
H12C_3 H 0.3592 0.7205 0.2038 0.040 Uiso 1 1 calc R U . . .
C13_3 C 0.37739(14) 0.70173(16) 0.40499(13) 0.0185(6) Uani 1 1 d . . . . .
C14_3 C 0.31407(15) 0.73292(17) 0.40104(13) 0.0207(7) Uani 1 1 d . . . . .
C15_3 C 0.27075(15) 0.72246(18) 0.44879(13) 0.0244(7) Uani 1 1 d . . . . .
H15_3 H 0.2272 0.7427 0.4470 0.029 Uiso 1 1 calc R U . . .
C16_3 C 0.28926(16) 0.68364(17) 0.49865(13) 0.0242(7) Uani 1 1 d . . . . .
C17_3 C 0.35365(17) 0.65669(18) 0.50213(14) 0.0263(7) Uani 1 1 d . . . . .
H17_3 H 0.3671 0.6314 0.5370 0.032 Uiso 1 1 calc R U . . .
C18_3 C 0.39928(15) 0.66571(17) 0.45581(13) 0.0225(7) Uani 1 1 d . . . . .
C19_3 C 0.29383(17) 0.77963(19) 0.34964(14) 0.0290(8) Uani 1 1 d . . . . .
H19A_3 H 0.3298 0.8140 0.3405 0.044 Uiso 1 1 calc R U . . .
H19B_3 H 0.2532 0.8065 0.3599 0.044 Uiso 1 1 calc R U . . .
H19C_3 H 0.2852 0.7490 0.3148 0.044 Uiso 1 1 calc R U . . .
C20_3 C 0.24021(18) 0.6712(2) 0.54875(14) 0.0351(9) Uani 1 1 d . . . . .
H20A_3 H 0.2057 0.7089 0.5478 0.053 Uiso 1 1 calc R U . . .
H20B_3 H 0.2638 0.6731 0.5870 0.053 Uiso 1 1 calc R U . . .
H20C_3 H 0.2193 0.6234 0.5440 0.053 Uiso 1 1 calc R U . . .
C21_3 C 0.46998(18) 0.6407(2) 0.46406(16) 0.0387(9) Uani 1 1 d . . . . .
H21A_3 H 0.4938 0.6437 0.4260 0.058 Uiso 1 1 calc R U . . .
H21B_3 H 0.4701 0.5903 0.4781 0.058 Uiso 1 1 calc R U . . .
H21C_3 H 0.4922 0.6717 0.4934 0.058 Uiso 1 1 calc R U . . .
C1_4 C 0.32831(14) 0.51439(16) 0.25008(13) 0.0182(6) Uani 1 1 d . . . . .
N1_4 N 0.29913(12) 0.50217(14) 0.19613(10) 0.0203(6) Uani 1 1 d . . . . .
C2_4 C 0.24742(18) 0.45267(19) 0.20049(14) 0.0310(8) Uani 1 1 d . . . . .
H2_4 H 0.2194 0.4366 0.1690 0.037 Uiso 1 1 calc R U . . .
N2_4 N 0.29465(12) 0.46915(14) 0.28708(10) 0.0193(5) Uani 1 1 d . . . . .
C3_4 C 0.24434(17) 0.43174(19) 0.25746(14) 0.0299(8) Uani 1 1 d . . . . .
H3_4 H 0.2138 0.3980 0.2743 0.036 Uiso 1 1 calc R U . . .
C4_4 C 0.32113(15) 0.52986(17) 0.13919(12) 0.0200(6) Uani 1 1 d . . . . .
C5_4 C 0.36562(16) 0.48791(17) 0.10638(14) 0.0231(7) Uani 1 1 d . . . . .
C6_4 C 0.38518(16) 0.51294(18) 0.05057(13) 0.0239(7) Uani 1 1 d . . . . .
H6_4 H 0.4158 0.4853 0.0276 0.029 Uiso 1 1 calc R U . . .
C7_4 C 0.36065(16) 0.57752(18) 0.02818(13) 0.0247(7) Uani 1 1 d . . . . .
C8_4 C 0.31537(16) 0.61711(18) 0.06165(13) 0.0247(7) Uani 1 1 d . . . . .
H8_4 H 0.2983 0.6612 0.0459 0.030 Uiso 1 1 calc R U . . .
C9_4 C 0.29420(15) 0.59421(18) 0.11751(13) 0.0220(7) Uani 1 1 d . . . . .
C10_4 C 0.24254(16) 0.63541(19) 0.15232(14) 0.0283(8) Uani 1 1 d . . . . .
H10A_4 H 0.2334 0.6818 0.1326 0.042 Uiso 1 1 calc R U . . .
H10B_4 H 0.2592 0.6444 0.1927 0.042 Uiso 1 1 calc R U . . .
H10C_4 H 0.2013 0.6068 0.1544 0.042 Uiso 1 1 calc R U . . .
C11_4 C 0.39259(18) 0.41697(18) 0.13009(15) 0.0303(8) Uani 1 1 d . . . . .
H11A_4 H 0.3563 0.3814 0.1326 0.045 Uiso 1 1 calc R U . . .
H11B_4 H 0.4116 0.4247 0.1698 0.045 Uiso 1 1 calc R U . . .
H11C_4 H 0.4273 0.3987 0.1033 0.045 Uiso 1 1 calc R U . . .
C12_4 C 0.38123(18) 0.6040(2) -0.03281(14) 0.0326(8) Uani 1 1 d . . . . .
H12A_4 H 0.3454 0.5939 -0.0614 0.049 Uiso 1 1 calc R U . . .
H12B_4 H 0.4220 0.5788 -0.0453 0.049 Uiso 1 1 calc R U . . .
H12C_4 H 0.3896 0.6564 -0.0313 0.049 Uiso 1 1 calc R U . . .
C13_4 C 0.31107(15) 0.45694(16) 0.34902(13) 0.0189(6) Uani 1 1 d . . . . .
C14_4 C 0.35827(15) 0.40388(17) 0.36222(13) 0.0210(6) Uani 1 1 d . . . . .
C15_4 C 0.37372(15) 0.39255(18) 0.42188(14) 0.0250(7) Uani 1 1 d . . . . .
H15_4 H 0.4062 0.3571 0.4321 0.030 Uiso 1 1 calc R U . . .
C16_4 C 0.34274(15) 0.43184(19) 0.46698(13) 0.0251(7) Uani 1 1 d . . . . .
C17_4 C 0.29474(15) 0.48240(18) 0.45161(13) 0.0238(7) Uani 1 1 d . . . . .
H17_4 H 0.2727 0.5086 0.4823 0.029 Uiso 1 1 calc R U . . .
C18_4 C 0.27775(14) 0.49617(17) 0.39242(13) 0.0189(6) Uani 1 1 d . . . . .
C19_4 C 0.39139(17) 0.36012(18) 0.31418(15) 0.0286(8) Uani 1 1 d . . . . .
H19A_4 H 0.3580 0.3299 0.2941 0.043 Uiso 1 1 calc R U . . .
H19B_4 H 0.4258 0.3290 0.3318 0.043 Uiso 1 1 calc R U . . .
H19C_4 H 0.4120 0.3929 0.2852 0.043 Uiso 1 1 calc R U . . .
C20_4 C 0.36215(18) 0.4213(2) 0.53115(15) 0.0407(10) Uani 1 1 d . . . . .
H20A_4 H 0.3657 0.3693 0.5398 0.061 Uiso 1 1 calc R U . . .
H20B_4 H 0.3281 0.4431 0.5569 0.061 Uiso 1 1 calc R U . . .
H20C_4 H 0.4053 0.4448 0.5385 0.061 Uiso 1 1 calc R U . . .
C21_4 C 0.22482(16) 0.55106(18) 0.37713(14) 0.0254(7) Uani 1 1 d . . . . .
H21A_4 H 0.2442 0.5892 0.3521 0.038 Uiso 1 1 calc R U . . .
H21B_4 H 0.2073 0.5727 0.4138 0.038 Uiso 1 1 calc R U . . .
H21C_4 H 0.1885 0.5271 0.3555 0.038 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 F1_2 1.8591(18) . ?
Ni1 C1_1 1.883(3) . ?
Ni1 C1_3 1.920(3) . ?
Ni1 C1_4 1.923(3) . ?
C1_1 C2_1 1.377(4) . ?
C1_1 C5_1 1.391(4) . ?
F1_1 C2_1 1.344(4) . ?
N1_1 C4_1 1.314(5) . ?
N1_1 C3_1 1.317(5) . ?
C2_1 C3_1 1.381(5) . ?
F2_1 C3_1 1.342(4) . ?
F3_1 C4_1 1.355(4) . ?
C4_1 C5_1 1.372(5) . ?
F4_1 C5_1 1.338(4) . ?
C1_3 N2_3 1.353(4) . ?
C1_3 N1_3 1.370(4) . ?
N1_3 C2_3 1.379(4) . ?
N1_3 C13_3 1.453(4) . ?
C2_3 C3_3 1.336(4) . ?
C2_3 H2_3 0.9500 . ?
N2_3 C3_3 1.391(4) . ?
N2_3 C4_3 1.446(3) . ?
C3_3 H3_3 0.9500 . ?
C4_3 C5_3 1.389(4) . ?
C4_3 C9_3 1.401(4) . ?
C5_3 C6_3 1.392(4) . ?
C5_3 C10_3 1.509(4) . ?
C6_3 C7_3 1.390(4) . ?
C6_3 H6_3 0.9500 . ?
C7_3 C8_3 1.387(5) . ?
C7_3 C11_3 1.512(4) . ?
C8_3 C9_3 1.391(4) . ?
C8_3 H8_3 0.9500 . ?
C9_3 C12_3 1.503(4) . ?
C10_3 H10A_3 0.9800 . ?
C10_3 H10B_3 0.9800 . ?
C10_3 H10C_3 0.9800 . ?
C11_3 H11A_3 0.9800 . ?
C11_3 H11B_3 0.9800 . ?
C11_3 H11C_3 0.9800 . ?
C12_3 H12A_3 0.9800 . ?
C12_3 H12B_3 0.9800 . ?
C12_3 H12C_3 0.9800 . ?
C13_3 C18_3 1.391(4) . ?
C13_3 C14_3 1.395(4) . ?
C14_3 C15_3 1.393(4) . ?
C14_3 C19_3 1.496(4) . ?
C15_3 C16_3 1.380(4) . ?
C15_3 H15_3 0.9500 . ?
C16_3 C17_3 1.384(5) . ?
C16_3 C20_3 1.511(4) . ?
C17_3 C18_3 1.395(4) . ?
C17_3 H17_3 0.9500 . ?
C18_3 C21_3 1.501(4) . ?
C19_3 H19A_3 0.9800 . ?
C19_3 H19B_3 0.9800 . ?
C19_3 H19C_3 0.9800 . ?
C20_3 H20A_3 0.9800 . ?
C20_3 H20B_3 0.9800 . ?
C20_3 H20C_3 0.9800 . ?
C21_3 H21A_3 0.9800 . ?
C21_3 H21B_3 0.9800 . ?
C21_3 H21C_3 0.9800 . ?
C1_4 N2_4 1.356(4) . ?
C1_4 N1_4 1.364(4) . ?
N1_4 C2_4 1.383(4) . ?
N1_4 C4_4 1.446(4) . ?
C2_4 C3_4 1.338(5) . ?
C2_4 H2_4 0.9500 . ?
N2_4 C3_4 1.390(4) . ?
N2_4 C13_4 1.447(4) . ?
C3_4 H3_4 0.9500 . ?
C4_4 C9_4 1.390(4) . ?
C4_4 C5_4 1.391(4) . ?
C5_4 C6_4 1.392(4) . ?
C5_4 C11_4 1.511(4) . ?
C6_4 C7_4 1.382(4) . ?
C6_4 H6_4 0.9500 . ?
C7_4 C8_4 1.386(4) . ?
C7_4 C12_4 1.511(4) . ?
C8_4 C9_4 1.390(4) . ?
C8_4 H8_4 0.9500 . ?
C9_4 C10_4 1.503(4) . ?
C10_4 H10A_4 0.9800 . ?
C10_4 H10B_4 0.9800 . ?
C10_4 H10C_4 0.9800 . ?
C11_4 H11A_4 0.9800 . ?
C11_4 H11B_4 0.9800 . ?
C11_4 H11C_4 0.9800 . ?
C12_4 H12A_4 0.9800 . ?
C12_4 H12B_4 0.9800 . ?
C12_4 H12C_4 0.9800 . ?
C13_4 C18_4 1.385(4) . ?
C13_4 C14_4 1.392(4) . ?
C14_4 C15_4 1.391(4) . ?
C14_4 C19_4 1.501(4) . ?
C15_4 C16_4 1.391(5) . ?
C15_4 H15_4 0.9500 . ?
C16_4 C17_4 1.382(4) . ?
C16_4 C20_4 1.505(4) . ?
C17_4 C18_4 1.396(4) . ?
C17_4 H17_4 0.9500 . ?
C18_4 C21_4 1.505(4) . ?
C19_4 H19A_4 0.9800 . ?
C19_4 H19B_4 0.9800 . ?
C19_4 H19C_4 0.9800 . ?
C20_4 H20A_4 0.9800 . ?
C20_4 H20B_4 0.9800 . ?
C20_4 H20C_4 0.9800 . ?
C21_4 H21A_4 0.9800 . ?
C21_4 H21B_4 0.9800 . ?
C21_4 H21C_4 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
F1_2 Ni1 C1_1 178.20(11) . . ?
F1_2 Ni1 C1_3 89.60(10) . . ?
C1_1 Ni1 C1_3 91.95(12) . . ?
F1_2 Ni1 C1_4 84.72(10) . . ?
C1_1 Ni1 C1_4 93.73(12) . . ?
C1_3 Ni1 C1_4 174.31(12) . . ?
C2_1 C1_1 C5_1 112.1(3) . . ?
C2_1 C1_1 Ni1 125.2(2) . . ?
C5_1 C1_1 Ni1 122.6(2) . . ?
C4_1 N1_1 C3_1 114.4(3) . . ?
F1_1 C2_1 C1_1 120.2(3) . . ?
F1_1 C2_1 C3_1 117.1(3) . . ?
C1_1 C2_1 C3_1 122.7(3) . . ?
N1_1 C3_1 F2_1 115.9(3) . . ?
N1_1 C3_1 C2_1 123.9(3) . . ?
F2_1 C3_1 C2_1 120.1(3) . . ?
N1_1 C4_1 F3_1 115.1(3) . . ?
N1_1 C4_1 C5_1 125.2(3) . . ?
F3_1 C4_1 C5_1 119.7(4) . . ?
F4_1 C5_1 C4_1 117.2(3) . . ?
F4_1 C5_1 C1_1 121.2(3) . . ?
C4_1 C5_1 C1_1 121.6(3) . . ?
N2_3 C1_3 N1_3 103.3(2) . . ?
N2_3 C1_3 Ni1 126.7(2) . . ?
N1_3 C1_3 Ni1 129.9(2) . . ?
C1_3 N1_3 C2_3 111.1(2) . . ?
C1_3 N1_3 C13_3 127.6(3) . . ?
C2_3 N1_3 C13_3 121.1(2) . . ?
C3_3 C2_3 N1_3 107.6(3) . . ?
C3_3 C2_3 H2_3 126.2 . . ?
N1_3 C2_3 H2_3 126.2 . . ?
C1_3 N2_3 C3_3 112.0(2) . . ?
C1_3 N2_3 C4_3 126.3(2) . . ?
C3_3 N2_3 C4_3 121.3(2) . . ?
C2_3 C3_3 N2_3 106.0(3) . . ?
C2_3 C3_3 H3_3 127.0 . . ?
N2_3 C3_3 H3_3 127.0 . . ?
C5_3 C4_3 C9_3 122.9(3) . . ?
C5_3 C4_3 N2_3 118.8(3) . . ?
C9_3 C4_3 N2_3 118.2(3) . . ?
C4_3 C5_3 C6_3 117.7(3) . . ?
C4_3 C5_3 C10_3 122.3(3) . . ?
C6_3 C5_3 C10_3 120.0(3) . . ?
C7_3 C6_3 C5_3 121.5(3) . . ?
C7_3 C6_3 H6_3 119.2 . . ?
C5_3 C6_3 H6_3 119.2 . . ?
C8_3 C7_3 C6_3 118.7(3) . . ?
C8_3 C7_3 C11_3 121.1(3) . . ?
C6_3 C7_3 C11_3 120.3(3) . . ?
C7_3 C8_3 C9_3 122.3(3) . . ?
C7_3 C8_3 H8_3 118.8 . . ?
C9_3 C8_3 H8_3 118.8 . . ?
C8_3 C9_3 C4_3 116.8(3) . . ?
C8_3 C9_3 C12_3 121.3(3) . . ?
C4_3 C9_3 C12_3 121.9(3) . . ?
C5_3 C10_3 H10A_3 109.5 . . ?
C5_3 C10_3 H10B_3 109.5 . . ?
H10A_3 C10_3 H10B_3 109.5 . . ?
C5_3 C10_3 H10C_3 109.5 . . ?
H10A_3 C10_3 H10C_3 109.5 . . ?
H10B_3 C10_3 H10C_3 109.5 . . ?
C7_3 C11_3 H11A_3 109.5 . . ?
C7_3 C11_3 H11B_3 109.5 . . ?
H11A_3 C11_3 H11B_3 109.5 . . ?
C7_3 C11_3 H11C_3 109.5 . . ?
H11A_3 C11_3 H11C_3 109.5 . . ?
H11B_3 C11_3 H11C_3 109.5 . . ?
C9_3 C12_3 H12A_3 109.5 . . ?
C9_3 C12_3 H12B_3 109.5 . . ?
H12A_3 C12_3 H12B_3 109.5 . . ?
C9_3 C12_3 H12C_3 109.5 . . ?
H12A_3 C12_3 H12C_3 109.5 . . ?
H12B_3 C12_3 H12C_3 109.5 . . ?
C18_3 C13_3 C14_3 122.3(3) . . ?
C18_3 C13_3 N1_3 119.4(3) . . ?
C14_3 C13_3 N1_3 117.9(3) . . ?
C15_3 C14_3 C13_3 117.4(3) . . ?
C15_3 C14_3 C19_3 120.3(3) . . ?
C13_3 C14_3 C19_3 122.2(3) . . ?
C16_3 C15_3 C14_3 122.0(3) . . ?
C16_3 C15_3 H15_3 119.0 . . ?
C14_3 C15_3 H15_3 119.0 . . ?
C15_3 C16_3 C17_3 118.8(3) . . ?
C15_3 C16_3 C20_3 120.6(3) . . ?
C17_3 C16_3 C20_3 120.6(3) . . ?
C16_3 C17_3 C18_3 121.7(3) . . ?
C16_3 C17_3 H17_3 119.1 . . ?
C18_3 C17_3 H17_3 119.1 . . ?
C13_3 C18_3 C17_3 117.5(3) . . ?
C13_3 C18_3 C21_3 123.0(3) . . ?
C17_3 C18_3 C21_3 119.3(3) . . ?
C14_3 C19_3 H19A_3 109.5 . . ?
C14_3 C19_3 H19B_3 109.5 . . ?
H19A_3 C19_3 H19B_3 109.5 . . ?
C14_3 C19_3 H19C_3 109.5 . . ?
H19A_3 C19_3 H19C_3 109.5 . . ?
H19B_3 C19_3 H19C_3 109.5 . . ?
C16_3 C20_3 H20A_3 109.5 . . ?
C16_3 C20_3 H20B_3 109.5 . . ?
H20A_3 C20_3 H20B_3 109.5 . . ?
C16_3 C20_3 H20C_3 109.5 . . ?
H20A_3 C20_3 H20C_3 109.5 . . ?
H20B_3 C20_3 H20C_3 109.5 . . ?
C18_3 C21_3 H21A_3 109.5 . . ?
C18_3 C21_3 H21B_3 109.5 . . ?
H21A_3 C21_3 H21B_3 109.5 . . ?
C18_3 C21_3 H21C_3 109.5 . . ?
H21A_3 C21_3 H21C_3 109.5 . . ?
H21B_3 C21_3 H21C_3 109.5 . . ?
N2_4 C1_4 N1_4 103.3(2) . . ?
N2_4 C1_4 Ni1 123.9(2) . . ?
N1_4 C1_4 Ni1 130.5(2) . . ?
C1_4 N1_4 C2_4 111.5(2) . . ?
C1_4 N1_4 C4_4 126.7(2) . . ?
C2_4 N1_4 C4_4 121.6(2) . . ?
C3_4 C2_4 N1_4 107.0(3) . . ?
C3_4 C2_4 H2_4 126.5 . . ?
N1_4 C2_4 H2_4 126.5 . . ?
C1_4 N2_4 C3_4 111.8(2) . . ?
C1_4 N2_4 C13_4 124.9(2) . . ?
C3_4 N2_4 C13_4 123.2(2) . . ?
C2_4 C3_4 N2_4 106.3(3) . . ?
C2_4 C3_4 H3_4 126.8 . . ?
N2_4 C3_4 H3_4 126.8 . . ?
C9_4 C4_4 C5_4 122.5(3) . . ?
C9_4 C4_4 N1_4 119.5(3) . . ?
C5_4 C4_4 N1_4 117.9(3) . . ?
C4_4 C5_4 C6_4 118.3(3) . . ?
C4_4 C5_4 C11_4 121.5(3) . . ?
C6_4 C5_4 C11_4 120.2(3) . . ?
C7_4 C6_4 C5_4 120.9(3) . . ?
C7_4 C6_4 H6_4 119.6 . . ?
C5_4 C6_4 H6_4 119.6 . . ?
C6_4 C7_4 C8_4 119.2(3) . . ?
C6_4 C7_4 C12_4 120.7(3) . . ?
C8_4 C7_4 C12_4 120.0(3) . . ?
C7_4 C8_4 C9_4 122.0(3) . . ?
C7_4 C8_4 H8_4 119.0 . . ?
C9_4 C8_4 H8_4 119.0 . . ?
C8_4 C9_4 C4_4 117.2(3) . . ?
C8_4 C9_4 C10_4 121.8(3) . . ?
C4_4 C9_4 C10_4 121.0(3) . . ?
C9_4 C10_4 H10A_4 109.5 . . ?
C9_4 C10_4 H10B_4 109.5 . . ?
H10A_4 C10_4 H10B_4 109.5 . . ?
C9_4 C10_4 H10C_4 109.5 . . ?
H10A_4 C10_4 H10C_4 109.5 . . ?
H10B_4 C10_4 H10C_4 109.5 . . ?
C5_4 C11_4 H11A_4 109.5 . . ?
C5_4 C11_4 H11B_4 109.5 . . ?
H11A_4 C11_4 H11B_4 109.5 . . ?
C5_4 C11_4 H11C_4 109.5 . . ?
H11A_4 C11_4 H11C_4 109.5 . . ?
H11B_4 C11_4 H11C_4 109.5 . . ?
C7_4 C12_4 H12A_4 109.5 . . ?
C7_4 C12_4 H12B_4 109.5 . . ?
H12A_4 C12_4 H12B_4 109.5 . . ?
C7_4 C12_4 H12C_4 109.5 . . ?
H12A_4 C12_4 H12C_4 109.5 . . ?
H12B_4 C12_4 H12C_4 109.5 . . ?
C18_4 C13_4 C14_4 122.9(3) . . ?
C18_4 C13_4 N2_4 119.1(3) . . ?
C14_4 C13_4 N2_4 117.9(3) . . ?
C15_4 C14_4 C13_4 117.5(3) . . ?
C15_4 C14_4 C19_4 120.9(3) . . ?
C13_4 C14_4 C19_4 121.6(3) . . ?
C16_4 C15_4 C14_4 121.6(3) . . ?
C16_4 C15_4 H15_4 119.2 . . ?
C14_4 C15_4 H15_4 119.2 . . ?
C17_4 C16_4 C15_4 118.6(3) . . ?
C17_4 C16_4 C20_4 120.4(3) . . ?
C15_4 C16_4 C20_4 121.0(3) . . ?
C16_4 C17_4 C18_4 122.0(3) . . ?
C16_4 C17_4 H17_4 119.0 . . ?
C18_4 C17_4 H17_4 119.0 . . ?
C13_4 C18_4 C17_4 117.3(3) . . ?
C13_4 C18_4 C21_4 122.0(3) . . ?
C17_4 C18_4 C21_4 120.8(3) . . ?
C14_4 C19_4 H19A_4 109.5 . . ?
C14_4 C19_4 H19B_4 109.5 . . ?
H19A_4 C19_4 H19B_4 109.5 . . ?
C14_4 C19_4 H19C_4 109.5 . . ?
H19A_4 C19_4 H19C_4 109.5 . . ?
H19B_4 C19_4 H19C_4 109.5 . . ?
C16_4 C20_4 H20A_4 109.5 . . ?
C16_4 C20_4 H20B_4 109.5 . . ?
H20A_4 C20_4 H20B_4 109.5 . . ?
C16_4 C20_4 H20C_4 109.5 . . ?
H20A_4 C20_4 H20C_4 109.5 . . ?
H20B_4 C20_4 H20C_4 109.5 . . ?
C18_4 C21_4 H21A_4 109.5 . . ?
C18_4 C21_4 H21B_4 109.5 . . ?
H21A_4 C21_4 H21B_4 109.5 . . ?
C18_4 C21_4 H21C_4 109.5 . . ?
H21A_4 C21_4 H21C_4 109.5 . . ?
H21B_4 C21_4 H21C_4 109.5 . . ?

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
C1_3 Ni1 C1_1 C2_1 -105.8(3) . . . . ?
C1_4 Ni1 C1_1 C2_1 74.6(3) . . . . ?
C1_3 Ni1 C1_1 C5_1 77.9(3) . . . . ?
C1_4 Ni1 C1_1 C5_1 -101.6(3) . . . . ?
C5_1 C1_1 C2_1 F1_1 -178.3(3) . . . . ?
Ni1 C1_1 C2_1 F1_1 5.0(4) . . . . ?
C5_1 C1_1 C2_1 C3_1 1.5(4) . . . . ?
Ni1 C1_1 C2_1 C3_1 -175.1(2) . . . . ?
C4_1 N1_1 C3_1 F2_1 -179.7(3) . . . . ?
C4_1 N1_1 C3_1 C2_1 -0.8(5) . . . . ?
F1_1 C2_1 C3_1 N1_1 179.3(3) . . . . ?
C1_1 C2_1 C3_1 N1_1 -0.6(5) . . . . ?
F1_1 C2_1 C3_1 F2_1 -1.8(4) . . . . ?
C1_1 C2_1 C3_1 F2_1 178.3(3) . . . . ?
C3_1 N1_1 C4_1 F3_1 -180.0(3) . . . . ?
C3_1 N1_1 C4_1 C5_1 1.1(5) . . . . ?
N1_1 C4_1 C5_1 F4_1 178.7(3) . . . . ?
F3_1 C4_1 C5_1 F4_1 -0.2(5) . . . . ?
N1_1 C4_1 C5_1 C1_1 0.0(6) . . . . ?
F3_1 C4_1 C5_1 C1_1 -178.9(3) . . . . ?
C2_1 C1_1 C5_1 F4_1 -180.0(3) . . . . ?
Ni1 C1_1 C5_1 F4_1 -3.2(4) . . . . ?
C2_1 C1_1 C5_1 C4_1 -1.3(5) . . . . ?
Ni1 C1_1 C5_1 C4_1 175.5(3) . . . . ?
N2_3 C1_3 N1_3 C2_3 0.4(3) . . . . ?
Ni1 C1_3 N1_3 C2_3 -176.6(2) . . . . ?
N2_3 C1_3 N1_3 C13_3 174.8(3) . . . . ?
Ni1 C1_3 N1_3 C13_3 -2.2(5) . . . . ?
C1_3 N1_3 C2_3 C3_3 -0.3(4) . . . . ?
C13_3 N1_3 C2_3 C3_3 -175.1(3) . . . . ?
N1_3 C1_3 N2_3 C3_3 -0.4(3) . . . . ?
Ni1 C1_3 N2_3 C3_3 176.7(2) . . . . ?
N1_3 C1_3 N2_3 C4_3 -173.9(3) . . . . ?
Ni1 C1_3 N2_3 C4_3 3.3(4) . . . . ?
N1_3 C2_3 C3_3 N2_3 0.1(4) . . . . ?
C1_3 N2_3 C3_3 C2_3 0.2(4) . . . . ?
C4_3 N2_3 C3_3 C2_3 174.1(3) . . . . ?
C1_3 N2_3 C4_3 C5_3 -111.0(3) . . . . ?
C3_3 N2_3 C4_3 C5_3 76.1(4) . . . . ?
C1_3 N2_3 C4_3 C9_3 72.9(4) . . . . ?
C3_3 N2_3 C4_3 C9_3 -100.0(3) . . . . ?
C9_3 C4_3 C5_3 C6_3 -1.2(5) . . . . ?
N2_3 C4_3 C5_3 C6_3 -177.0(3) . . . . ?
C9_3 C4_3 C5_3 C10_3 177.8(3) . . . . ?
N2_3 C4_3 C5_3 C10_3 1.9(4) . . . . ?
C4_3 C5_3 C6_3 C7_3 -0.4(5) . . . . ?
C10_3 C5_3 C6_3 C7_3 -179.4(3) . . . . ?
C5_3 C6_3 C7_3 C8_3 1.1(5) . . . . ?
C5_3 C6_3 C7_3 C11_3 -178.5(3) . . . . ?
C6_3 C7_3 C8_3 C9_3 -0.3(5) . . . . ?
C11_3 C7_3 C8_3 C9_3 179.3(3) . . . . ?
C7_3 C8_3 C9_3 C4_3 -1.1(5) . . . . ?
C7_3 C8_3 C9_3 C12_3 177.0(3) . . . . ?
C5_3 C4_3 C9_3 C8_3 1.9(5) . . . . ?
N2_3 C4_3 C9_3 C8_3 177.8(3) . . . . ?
C5_3 C4_3 C9_3 C12_3 -176.2(3) . . . . ?
N2_3 C4_3 C9_3 C12_3 -0.4(4) . . . . ?
C1_3 N1_3 C13_3 C18_3 101.2(4) . . . . ?
C2_3 N1_3 C13_3 C18_3 -85.0(4) . . . . ?
C1_3 N1_3 C13_3 C14_3 -86.1(4) . . . . ?
C2_3 N1_3 C13_3 C14_3 87.7(4) . . . . ?
C18_3 C13_3 C14_3 C15_3 -4.4(5) . . . . ?
N1_3 C13_3 C14_3 C15_3 -176.9(3) . . . . ?
C18_3 C13_3 C14_3 C19_3 172.0(3) . . . . ?
N1_3 C13_3 C14_3 C19_3 -0.5(4) . . . . ?
C13_3 C14_3 C15_3 C16_3 0.8(5) . . . . ?
C19_3 C14_3 C15_3 C16_3 -175.7(3) . . . . ?
C14_3 C15_3 C16_3 C17_3 2.5(5) . . . . ?
C14_3 C15_3 C16_3 C20_3 -177.9(3) . . . . ?
C15_3 C16_3 C17_3 C18_3 -2.2(5) . . . . ?
C20_3 C16_3 C17_3 C18_3 178.2(3) . . . . ?
C14_3 C13_3 C18_3 C17_3 4.7(5) . . . . ?
N1_3 C13_3 C18_3 C17_3 177.1(3) . . . . ?
C14_3 C13_3 C18_3 C21_3 -171.5(3) . . . . ?
N1_3 C13_3 C18_3 C21_3 0.9(5) . . . . ?
C16_3 C17_3 C18_3 C13_3 -1.3(5) . . . . ?
C16_3 C17_3 C18_3 C21_3 175.0(3) . . . . ?
N2_4 C1_4 N1_4 C2_4 2.1(3) . . . . ?
Ni1 C1_4 N1_4 C2_4 -160.8(3) . . . . ?
N2_4 C1_4 N1_4 C4_4 -172.0(3) . . . . ?
Ni1 C1_4 N1_4 C4_4 25.2(5) . . . . ?
C1_4 N1_4 C2_4 C3_4 -1.4(4) . . . . ?
C4_4 N1_4 C2_4 C3_4 173.1(3) . . . . ?
N1_4 C1_4 N2_4 C3_4 -2.1(3) . . . . ?
Ni1 C1_4 N2_4 C3_4 162.2(2) . . . . ?
N1_4 C1_4 N2_4 C13_4 174.1(3) . . . . ?
Ni1 C1_4 N2_4 C13_4 -21.6(4) . . . . ?
N1_4 C2_4 C3_4 N2_4 0.0(4) . . . . ?
C1_4 N2_4 C3_4 C2_4 1.4(4) . . . . ?
C13_4 N2_4 C3_4 C2_4 -174.9(3) . . . . ?
C1_4 N1_4 C4_4 C9_4 -93.5(4) . . . . ?
C2_4 N1_4 C4_4 C9_4 93.0(4) . . . . ?
C1_4 N1_4 C4_4 C5_4 90.7(4) . . . . ?
C2_4 N1_4 C4_4 C5_4 -82.8(4) . . . . ?
C9_4 C4_4 C5_4 C6_4 2.0(5) . . . . ?
N1_4 C4_4 C5_4 C6_4 177.7(3) . . . . ?
C9_4 C4_4 C5_4 C11_4 -178.1(3) . . . . ?
N1_4 C4_4 C5_4 C11_4 -2.4(4) . . . . ?
C4_4 C5_4 C6_4 C7_4 -0.5(5) . . . . ?
C11_4 C5_4 C6_4 C7_4 179.6(3) . . . . ?
C5_4 C6_4 C7_4 C8_4 -0.8(5) . . . . ?
C5_4 C6_4 C7_4 C12_4 -179.1(3) . . . . ?
C6_4 C7_4 C8_4 C9_4 0.6(5) . . . . ?
C12_4 C7_4 C8_4 C9_4 178.9(3) . . . . ?
C7_4 C8_4 C9_4 C4_4 0.9(5) . . . . ?
C7_4 C8_4 C9_4 C10_4 -176.9(3) . . . . ?
C5_4 C4_4 C9_4 C8_4 -2.2(5) . . . . ?
N1_4 C4_4 C9_4 C8_4 -177.8(3) . . . . ?
C5_4 C4_4 C9_4 C10_4 175.6(3) . . . . ?
N1_4 C4_4 C9_4 C10_4 -0.1(4) . . . . ?
C1_4 N2_4 C13_4 C18_4 95.8(4) . . . . ?
C3_4 N2_4 C13_4 C18_4 -88.4(4) . . . . ?
C1_4 N2_4 C13_4 C14_4 -86.6(4) . . . . ?
C3_4 N2_4 C13_4 C14_4 89.2(4) . . . . ?
C18_4 C13_4 C14_4 C15_4 -2.5(5) . . . . ?
N2_4 C13_4 C14_4 C15_4 180.0(3) . . . . ?
C18_4 C13_4 C14_4 C19_4 177.4(3) . . . . ?
N2_4 C13_4 C14_4 C19_4 -0.2(4) . . . . ?
C13_4 C14_4 C15_4 C16_4 0.9(5) . . . . ?
C19_4 C14_4 C15_4 C16_4 -179.0(3) . . . . ?
C14_4 C15_4 C16_4 C17_4 1.0(5) . . . . ?
C14_4 C15_4 C16_4 C20_4 -177.3(3) . . . . ?
C15_4 C16_4 C17_4 C18_4 -1.5(5) . . . . ?
C20_4 C16_4 C17_4 C18_4 176.8(3) . . . . ?
C14_4 C13_4 C18_4 C17_4 2.1(4) . . . . ?
N2_4 C13_4 C18_4 C17_4 179.6(3) . . . . ?
C14_4 C13_4 C18_4 C21_4 -177.4(3) . . . . ?
N2_4 C13_4 C18_4 C21_4 0.1(4) . . . . ?
C16_4 C17_4 C18_4 C13_4 0.0(5) . . . . ?
C16_4 C17_4 C18_4 C21_4 179.4(3) . . . . ?

_refine_diff_density_max         0.883
_refine_diff_density_min         -0.940
_refine_diff_density_rms         0.084

####################################################################### 
# 
# 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_Compound_14
_database_code_depnum_ccdc_archive 'CCDC 2017699'
loop_
_audit_author_name
_audit_author_address
'Udo Radius'
;University Wuerzburg
Germany
;
_audit_update_record             
;
2020-07-20 deposited with the CCDC.	2020-10-06 downloaded from the CCDC.
;


_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C48 H50 F3 N4 Ni'
_chemical_formula_sum            'C48 H50 F3 N4 Ni'
_chemical_formula_weight         798.63

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   13.8929(5)
_cell_length_b                   10.8012(4)
_cell_length_c                   27.4228(9)
_cell_angle_alpha                90
_cell_angle_beta                 91.771(2)
_cell_angle_gamma                90
_cell_volume                     4113.1(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9826
_cell_measurement_theta_min      2.39
_cell_measurement_theta_max      30.28

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.290
_exptl_crystal_F_000             1684
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.310
_exptl_crystal_size_mid          0.131
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.524
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6956
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   
'SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_monochromator  helios
_diffrn_measurement_device_type  'Bruker X8-APEX II'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            85250
_diffrn_reflns_av_unetI/netI     0.0383
_diffrn_reflns_av_R_equivalents  0.0596
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_theta_min         2.389
_diffrn_reflns_theta_max         30.522
_diffrn_reflns_theta_full        26.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             12539
_reflns_number_gt                10035
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0439P)²+1.5736P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         12539
_refine_ls_number_parameters     587
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0527
_refine_ls_R_factor_gt           0.0370
_refine_ls_wR_factor_ref         0.0957
_refine_ls_wR_factor_gt          0.0883
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_restrained_S_all      1.020
_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
N1_1 N 0.21217(8) 0.84460(10) 0.27431(4) 0.0178(2) Uani 1 1 d . . . . .
N2_1 N 0.24332(8) 0.95041(10) 0.33877(4) 0.0172(2) Uani 1 1 d . . . . .
N1_2 N 0.27246(8) 0.42004(10) 0.38728(4) 0.0158(2) Uani 1 1 d . . . . .
N2_2 N 0.41597(8) 0.47652(10) 0.37236(4) 0.0170(2) Uani 1 1 d . . . . .
C1_10 C 0.32359(9) 0.52034(11) 0.37175(4) 0.0150(2) Uani 1 1 d . . . . .
C2_10 C 0.33111(10) 0.31804(12) 0.39651(5) 0.0207(3) Uani 1 1 d . . . . .
H2_10 H 0.311197 0.238688 0.407226 0.025 Uiso 1 1 calc R U . . .
C3_10 C 0.42146(10) 0.35340(13) 0.38734(5) 0.0216(3) Uani 1 1 d . . . . .
H3_10 H 0.477976 0.304165 0.390462 0.026 Uiso 1 1 calc R U . . .
C4_10 C 0.16907(9) 0.41698(11) 0.38831(5) 0.0160(2) Uani 1 1 d . . . . .
C5_10 C 0.11784(10) 0.41116(12) 0.34381(5) 0.0179(2) Uani 1 1 d . . . . .
C6_10 C 0.01793(10) 0.41230(13) 0.34442(5) 0.0204(3) Uani 1 1 d . . . . .
H6_10 H -0.017953 0.408354 0.314402 0.024 Uiso 1 1 calc R U . . .
C7_10 C -0.03110(10) 0.41910(13) 0.38795(5) 0.0201(3) Uani 1 1 d . . . . .
C8_10 C 0.02284(10) 0.42017(13) 0.43166(5) 0.0193(3) Uani 1 1 d . . . . .
H8_10 H -0.009816 0.421973 0.461577 0.023 Uiso 1 1 calc R U . . .
C9_10 C 0.12352(10) 0.41869(12) 0.43283(5) 0.0169(2) Uani 1 1 d . . . . .
C10_10 C 0.16961(11) 0.40474(14) 0.29640(5) 0.0229(3) Uani 1 1 d . . . . .
H10A_10 H 0.124796 0.376884 0.270365 0.034 Uiso 1 1 calc R U . . .
H10B_10 H 0.223327 0.346223 0.299664 0.034 Uiso 1 1 calc R U . . .
H10C_10 H 0.194371 0.486950 0.288336 0.034 Uiso 1 1 calc R U . . .
C11_10 C 0.17967(10) 0.42223(13) 0.48057(5) 0.0204(3) Uani 1 1 d . . . . .
H11A_10 H 0.135744 0.410425 0.507457 0.031 Uiso 1 1 calc R U . . .
H11B_10 H 0.211941 0.502547 0.484149 0.031 Uiso 1 1 calc R U . . .
H11C_10 H 0.227943 0.356044 0.481203 0.031 Uiso 1 1 calc R U . . .
C12_10 C -0.13925(11) 0.42610(17) 0.38708(6) 0.0298(3) Uani 1 1 d . . . . .
H12A_10 H -0.161845 0.424940 0.420582 0.045 Uiso 1 1 calc R U . . .
H12B_10 H -0.166113 0.355013 0.369111 0.045 Uiso 1 1 calc R U . . .
H12C_10 H -0.160265 0.502915 0.370991 0.045 Uiso 1 1 calc R U . . .
C13_10 C 0.49708(10) 0.54545(12) 0.35593(5) 0.0174(2) Uani 1 1 d . . . . .
C14_10 C 0.50374(10) 0.56750(13) 0.30579(5) 0.0200(3) Uani 1 1 d . . . . .
C15_10 C 0.58276(11) 0.63400(13) 0.29034(5) 0.0231(3) Uani 1 1 d . . . . .
H15_10 H 0.587653 0.652482 0.256635 0.028 Uiso 1 1 calc R U . . .
C16_10 C 0.65474(11) 0.67415(13) 0.32278(5) 0.0235(3) Uani 1 1 d . . . . .
C17_10 C 0.64748(11) 0.64619(13) 0.37212(5) 0.0231(3) Uani 1 1 d . . . . .
H17_10 H 0.697463 0.671411 0.394369 0.028 Uiso 1 1 calc R U . . .
C18_10 C 0.56858(10) 0.58203(13) 0.38961(5) 0.0202(3) Uani 1 1 d . . . . .
C19_10 C 0.56215(12) 0.55195(16) 0.44319(5) 0.0279(3) Uani 1 1 d . . . . .
H19A_10 H 0.606858 0.604829 0.462079 0.042 Uiso 1 1 calc R U . . .
H19B_10 H 0.579134 0.464868 0.448625 0.042 Uiso 1 1 calc R U . . .
H19C_10 H 0.496301 0.566629 0.453632 0.042 Uiso 1 1 calc R U . . .
C20_10 C 0.43057(11) 0.51505(15) 0.26971(5) 0.0265(3) Uani 1 1 d . . . . .
H20A_10 H 0.452539 0.528054 0.236486 0.040 Uiso 1 1 calc R U . . .
H20B_10 H 0.368638 0.556806 0.273543 0.040 Uiso 1 1 calc R U . . .
H20C_10 H 0.422952 0.426169 0.275655 0.040 Uiso 1 1 calc R U . . .
C21_10 C 0.73993(13) 0.74606(16) 0.30501(6) 0.0343(4) Uani 1 1 d . . . . .
H21A_10 H 0.796155 0.730116 0.326554 0.051 Uiso 1 1 calc R U . . .
H21B_10 H 0.725019 0.834736 0.305192 0.051 Uiso 1 1 calc R U . . .
H21C_10 H 0.753941 0.720025 0.271737 0.051 Uiso 1 1 calc R U . . .
C1_11 C 0.24336(9) 0.83072(12) 0.32203(5) 0.0162(2) Uani 1 1 d . . . . .
C2_11 C 0.19402(11) 0.96765(13) 0.26240(5) 0.0239(3) Uani 1 1 d . . . . .
H2_11 H 0.172130 0.998737 0.231607 0.029 Uiso 1 1 calc R U . . .
C3_11 C 0.21345(11) 1.03397(13) 0.30290(5) 0.0238(3) Uani 1 1 d . . . . .
H3_11 H 0.207864 1.121161 0.306365 0.029 Uiso 1 1 calc R U . . .
C4_11 C 0.19867(10) 0.74679(12) 0.23909(5) 0.0180(2) Uani 1 1 d . . . . .
C5_11 C 0.27178(10) 0.72321(13) 0.20660(5) 0.0223(3) Uani 1 1 d . . . . .
C6_11 C 0.25415(11) 0.63406(14) 0.17058(5) 0.0246(3) Uani 1 1 d . . . . .
H6_11 H 0.303483 0.615297 0.148517 0.030 Uiso 1 1 calc R U . . .
C7_11 C 0.16678(11) 0.57186(13) 0.16592(5) 0.0238(3) Uani 1 1 d . . . . .
C8_11 C 0.09576(11) 0.59808(13) 0.19915(5) 0.0232(3) Uani 1 1 d . . . . .
H8_11 H 0.035895 0.555738 0.196486 0.028 Uiso 1 1 calc R U . . .
C9_11 C 0.11042(10) 0.68509(13) 0.23629(5) 0.0199(3) Uani 1 1 d . . . . .
C10_11 C 0.36544(12) 0.79303(15) 0.20982(7) 0.0309(3) Uani 1 1 d . . . . .
H10A_11 H 0.412748 0.751840 0.189584 0.046 Uiso 1 1 calc R U . . .
H10B_11 H 0.389389 0.794823 0.243800 0.046 Uiso 1 1 calc R U . . .
H10C_11 H 0.355189 0.877924 0.198161 0.046 Uiso 1 1 calc R U . . .
C11_11 C 0.14868(13) 0.48015(15) 0.12512(6) 0.0320(4) Uani 1 1 d . . . . .
H11A_11 H 0.103189 0.416922 0.135640 0.048 Uiso 1 1 calc R U . . .
H11B_11 H 0.209510 0.440610 0.116812 0.048 Uiso 1 1 calc R U . . .
H11C_11 H 0.121608 0.523395 0.096433 0.048 Uiso 1 1 calc R U . . .
C12_11 C 0.03416(11) 0.70917(15) 0.27296(6) 0.0270(3) Uani 1 1 d . . . . .
H12A_11 H -0.026660 0.671529 0.261579 0.040 Uiso 1 1 calc R U . . .
H12B_11 H 0.025352 0.798646 0.276714 0.040 Uiso 1 1 calc R U . . .
H12C_11 H 0.054161 0.673010 0.304442 0.040 Uiso 1 1 calc R U . . .
C13_11 C 0.27172(10) 0.98955(12) 0.38719(5) 0.0167(2) Uani 1 1 d . . . . .
C14_11 C 0.20096(10) 1.03314(12) 0.41807(5) 0.0189(3) Uani 1 1 d . . . . .
C15_11 C 0.22994(10) 1.07122(12) 0.46467(5) 0.0203(3) Uani 1 1 d . . . . .
H15_11 H 0.182735 1.099145 0.486468 0.024 Uiso 1 1 calc R U . . .
C16_11 C 0.32616(11) 1.06956(13) 0.48025(5) 0.0205(3) Uani 1 1 d . . . . .
C17_11 C 0.39481(10) 1.02982(13) 0.44784(5) 0.0207(3) Uani 1 1 d . . . . .
H17_11 H 0.460889 1.031269 0.457825 0.025 Uiso 1 1 calc R U . . .
C18_11 C 0.36925(10) 0.98790(12) 0.40109(5) 0.0185(3) Uani 1 1 d . . . . .
C19_11 C 0.44450(11) 0.94223(16) 0.36714(5) 0.0278(3) Uani 1 1 d . . . . .
H19A_11 H 0.508001 0.972014 0.378404 0.042 Uiso 1 1 calc R U . . .
H19B_11 H 0.430174 0.973417 0.334148 0.042 Uiso 1 1 calc R U . . .
H19C_11 H 0.444347 0.851503 0.366747 0.042 Uiso 1 1 calc R U . . .
C20_11 C 0.09643(10) 1.04140(15) 0.40220(6) 0.0265(3) Uani 1 1 d . . . . .
H20A_11 H 0.056273 1.038050 0.430925 0.040 Uiso 1 1 calc R U . . .
H20B_11 H 0.080098 0.971951 0.380482 0.040 Uiso 1 1 calc R U . . .
H20C_11 H 0.084880 1.119584 0.384849 0.040 Uiso 1 1 calc R U . . .
C21_11 C 0.35489(12) 1.11019(16) 0.53116(5) 0.0296(3) Uani 1 1 d . . . . .
H21A_11 H 0.418042 1.150551 0.530843 0.044 Uiso 1 1 calc R U . . .
H21B_11 H 0.358298 1.037853 0.552710 0.044 Uiso 1 1 calc R U . . .
H21C_11 H 0.307023 1.168625 0.543053 0.044 Uiso 1 1 calc R U . . .
C1A_12 C 0.2220(6) 0.7175(12) 0.4184(4) 0.0184(17) Uani 0.484(3) 1 d . . P A 1
C2A_12 C 0.1243(8) 0.7341(11) 0.4299(4) 0.038(3) Uani 0.484(3) 1 d . . P A 1
C3A_12 C 0.0929(8) 0.7677(11) 0.4756(4) 0.039(3) Uani 0.484(3) 1 d . . P A 1
C4A_12 C 0.1503(12) 0.7842(15) 0.5155(4) 0.049(4) Uani 0.484(3) 1 d . . P A 1
H4A_12 H 0.128035 0.805716 0.546758 0.058 Uiso 0.484(3) 1 calc R U P A 1
C5A_12 C 0.2441(10) 0.7661(17) 0.5053(5) 0.036(3) Uani 0.484(3) 1 d . . P A 1
C6A_12 C 0.2779(8) 0.7345(16) 0.4612(5) 0.028(3) Uani 0.484(3) 1 d . . P A 1
H6A_12 H 0.345475 0.722805 0.459162 0.033 Uiso 0.484(3) 1 calc R U P A 1
F1A_12 F 0.05652(14) 0.72676(19) 0.39195(8) 0.0319(6) Uani 0.484(3) 1 d . . P A
1
F2A_12 F -0.0092(8) 0.7887(14) 0.4773(5) 0.067(4) Uani 0.484(3) 1 d . . P A 1
F3A_12 F 0.3072(10) 0.7838(15) 0.5481(5) 0.065(3) Uani 0.484(3) 1 d . . P A 1
C1B_12 C 0.2188(5) 0.7242(11) 0.4242(4) 0.021(2) Uani 0.516(3) 1 d G . P A 2
C2B_12 C 0.1196(5) 0.7397(9) 0.4261(3) 0.0206(19) Uani 0.516(3) 1 d G . P A 2
H2B_12 H 0.080244 0.727698 0.397540 0.025 Uiso 0.516(3) 1 calc R U P A 2
C3B_12 C 0.0782(6) 0.7729(9) 0.4697(3) 0.0277(18) Uani 0.516(3) 1 d G . P A 2
C4B_12 C 0.1358(10) 0.7906(12) 0.5114(3) 0.032(2) Uani 0.516(3) 1 d G . P A 2
H4B_12 H 0.107453 0.813252 0.541208 0.038 Uiso 0.516(3) 1 calc R U P A 2
C5B_12 C 0.2349(9) 0.7750(14) 0.5096(4) 0.033(3) Uani 0.516(3) 1 d G . P A 2
C6B_12 C 0.2764(6) 0.7418(14) 0.4660(5) 0.024(2) Uani 0.516(3) 1 d G . P A 2
F1B_12 F 0.37313(14) 0.72847(18) 0.46358(7) 0.0331(6) Uani 0.516(3) 1 d . . P A
2
F2B_12 F -0.0150(7) 0.7865(12) 0.4736(5) 0.047(2) Uani 0.516(3) 1 d . . P A 2
F3B_12 F 0.2940(8) 0.7901(12) 0.5470(4) 0.0430(16) Uani 0.516(3) 1 d . . P A 2
Ni1_12 Ni 0.27433(2) 0.68283(2) 0.35793(2) 0.01470(5) 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
N1_1 C1_11 1.3739(17) . ?
N1_1 C2_11 1.3898(17) . ?
N1_1 C4_11 1.4397(17) . ?
N2_1 C1_11 1.3720(16) . ?
N2_1 C3_11 1.3888(17) . ?
N2_1 C13_11 1.4371(17) . ?
N1_2 C1_10 1.3705(16) . ?
N1_2 C2_10 1.3890(17) . ?
N1_2 C4_10 1.4379(17) . ?
N2_2 C1_10 1.3675(17) . ?
N2_2 C3_10 1.3932(17) . ?
N2_2 C13_10 1.4347(17) . ?
C1_10 Ni1_12 1.9173(13) . ?
C2_10 C3_10 1.343(2) . ?
C2_10 H2_10 0.9500 . ?
C3_10 H3_10 0.9500 . ?
C4_10 C9_10 1.3926(18) . ?
C4_10 C5_10 1.3950(18) . ?
C5_10 C6_10 1.3888(19) . ?
C5_10 C10_10 1.5067(19) . ?
C6_10 C7_10 1.3945(19) . ?
C6_10 H6_10 0.9500 . ?
C7_10 C8_10 1.3938(19) . ?
C7_10 C12_10 1.504(2) . ?
C8_10 C9_10 1.3982(19) . ?
C8_10 H8_10 0.9500 . ?
C9_10 C11_10 1.5035(18) . ?
C10_10 H10A_10 0.9800 . ?
C10_10 H10B_10 0.9800 . ?
C10_10 H10C_10 0.9800 . ?
C11_10 H11A_10 0.9800 . ?
C11_10 H11B_10 0.9800 . ?
C11_10 H11C_10 0.9800 . ?
C12_10 H12A_10 0.9800 . ?
C12_10 H12B_10 0.9800 . ?
C12_10 H12C_10 0.9800 . ?
C13_10 C18_10 1.393(2) . ?
C13_10 C14_10 1.4015(18) . ?
C14_10 C15_10 1.389(2) . ?
C14_10 C20_10 1.507(2) . ?
C15_10 C16_10 1.387(2) . ?
C15_10 H15_10 0.9500 . ?
C16_10 C17_10 1.393(2) . ?
C16_10 C21_10 1.509(2) . ?
C17_10 C18_10 1.3945(19) . ?
C17_10 H17_10 0.9500 . ?
C18_10 C19_10 1.5100(19) . ?
C19_10 H19A_10 0.9800 . ?
C19_10 H19B_10 0.9800 . ?
C19_10 H19C_10 0.9800 . ?
C20_10 H20A_10 0.9800 . ?
C20_10 H20B_10 0.9800 . ?
C20_10 H20C_10 0.9800 . ?
C21_10 H21A_10 0.9800 . ?
C21_10 H21B_10 0.9800 . ?
C21_10 H21C_10 0.9800 . ?
C1_11 Ni1_12 1.9183(13) . ?
C2_11 C3_11 1.342(2) . ?
C2_11 H2_11 0.9500 . ?
C3_11 H3_11 0.9500 . ?
C4_11 C5_11 1.395(2) . ?
C4_11 C9_11 1.3955(19) . ?
C5_11 C6_11 1.396(2) . ?
C5_11 C10_11 1.504(2) . ?
C6_11 C7_11 1.390(2) . ?
C6_11 H6_11 0.9500 . ?
C7_11 C8_11 1.393(2) . ?
C7_11 C11_11 1.510(2) . ?
C8_11 C9_11 1.396(2) . ?
C8_11 H8_11 0.9500 . ?
C9_11 C12_11 1.506(2) . ?
C10_11 H10A_11 0.9800 . ?
C10_11 H10B_11 0.9800 . ?
C10_11 H10C_11 0.9800 . ?
C11_11 H11A_11 0.9800 . ?
C11_11 H11B_11 0.9800 . ?
C11_11 H11C_11 0.9800 . ?
C12_11 H12A_11 0.9800 . ?
C12_11 H12B_11 0.9800 . ?
C12_11 H12C_11 0.9800 . ?
C13_11 C18_11 1.3962(19) . ?
C13_11 C14_11 1.3987(19) . ?
C14_11 C15_11 1.390(2) . ?
C14_11 C20_11 1.506(2) . ?
C15_11 C16_11 1.391(2) . ?
C15_11 H15_11 0.9500 . ?
C16_11 C17_11 1.391(2) . ?
C16_11 C21_11 1.505(2) . ?
C17_11 C18_11 1.3954(19) . ?
C17_11 H17_11 0.9500 . ?
C18_11 C19_11 1.5044(19) . ?
C19_11 H19A_11 0.9800 . ?
C19_11 H19B_11 0.9800 . ?
C19_11 H19C_11 0.9800 . ?
C20_11 H20A_11 0.9800 . ?
C20_11 H20B_11 0.9800 . ?
C20_11 H20C_11 0.9800 . ?
C21_11 H21A_11 0.9800 . ?
C21_11 H21B_11 0.9800 . ?
C21_11 H21C_11 0.9800 . ?
C1A_12 C6A_12 1.400(7) . ?
C1A_12 C2A_12 1.414(8) . ?
C1A_12 Ni1_12 1.869(11) . ?
C2A_12 F1A_12 1.384(11) . ?
C2A_12 C3A_12 1.388(7) . ?
C3A_12 C4A_12 1.345(10) . ?
C3A_12 F2A_12 1.439(15) . ?
C4A_12 C5A_12 1.355(9) . ?
C4A_12 H4A_12 0.9500 . ?
C5A_12 C6A_12 1.353(9) . ?
C5A_12 F3A_12 1.456(18) . ?
C6A_12 H6A_12 0.9500 . ?
C1B_12 C2B_12 1.3900 . ?
C1B_12 C6B_12 1.3900 . ?
C1B_12 Ni1_12 2.047(8) . ?
C2B_12 C3B_12 1.3900 . ?
C2B_12 H2B_12 0.9500 . ?
C3B_12 F2B_12 1.310(12) . ?
C3B_12 C4B_12 1.3900 . ?
C4B_12 C5B_12 1.3900 . ?
C4B_12 H4B_12 0.9500 . ?
C5B_12 F3B_12 1.304(15) . ?
C5B_12 C6B_12 1.3900 . ?
C6B_12 F1B_12 1.355(8) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1_11 N1_1 C2_11 112.19(11) . . ?
C1_11 N1_1 C4_11 126.13(11) . . ?
C2_11 N1_1 C4_11 121.68(11) . . ?
C1_11 N2_1 C3_11 112.25(11) . . ?
C1_11 N2_1 C13_11 125.69(11) . . ?
C3_11 N2_1 C13_11 122.06(11) . . ?
C1_10 N1_2 C2_10 112.14(11) . . ?
C1_10 N1_2 C4_10 123.50(11) . . ?
C2_10 N1_2 C4_10 123.98(11) . . ?
C1_10 N2_2 C3_10 112.14(11) . . ?
C1_10 N2_2 C13_10 124.23(11) . . ?
C3_10 N2_2 C13_10 123.47(11) . . ?
N2_2 C1_10 N1_2 102.58(10) . . ?
N2_2 C1_10 Ni1_12 130.42(9) . . ?
N1_2 C1_10 Ni1_12 126.85(9) . . ?
C3_10 C2_10 N1_2 106.66(12) . . ?
C3_10 C2_10 H2_10 126.7 . . ?
N1_2 C2_10 H2_10 126.7 . . ?
C2_10 C3_10 N2_2 106.48(12) . . ?
C2_10 C3_10 H3_10 126.8 . . ?
N2_2 C3_10 H3_10 126.8 . . ?
C9_10 C4_10 C5_10 122.28(12) . . ?
C9_10 C4_10 N1_2 119.89(12) . . ?
C5_10 C4_10 N1_2 117.82(11) . . ?
C6_10 C5_10 C4_10 118.18(12) . . ?
C6_10 C5_10 C10_10 120.98(12) . . ?
C4_10 C5_10 C10_10 120.84(12) . . ?
C5_10 C6_10 C7_10 121.71(13) . . ?
C5_10 C6_10 H6_10 119.1 . . ?
C7_10 C6_10 H6_10 119.1 . . ?
C8_10 C7_10 C6_10 118.21(13) . . ?
C8_10 C7_10 C12_10 121.57(13) . . ?
C6_10 C7_10 C12_10 120.22(13) . . ?
C7_10 C8_10 C9_10 122.05(12) . . ?
C7_10 C8_10 H8_10 119.0 . . ?
C9_10 C8_10 H8_10 119.0 . . ?
C4_10 C9_10 C8_10 117.48(12) . . ?
C4_10 C9_10 C11_10 121.73(12) . . ?
C8_10 C9_10 C11_10 120.77(12) . . ?
C5_10 C10_10 H10A_10 109.5 . . ?
C5_10 C10_10 H10B_10 109.5 . . ?
H10A_10 C10_10 H10B_10 109.5 . . ?
C5_10 C10_10 H10C_10 109.5 . . ?
H10A_10 C10_10 H10C_10 109.5 . . ?
H10B_10 C10_10 H10C_10 109.5 . . ?
C9_10 C11_10 H11A_10 109.5 . . ?
C9_10 C11_10 H11B_10 109.5 . . ?
H11A_10 C11_10 H11B_10 109.5 . . ?
C9_10 C11_10 H11C_10 109.5 . . ?
H11A_10 C11_10 H11C_10 109.5 . . ?
H11B_10 C11_10 H11C_10 109.5 . . ?
C7_10 C12_10 H12A_10 109.5 . . ?
C7_10 C12_10 H12B_10 109.5 . . ?
H12A_10 C12_10 H12B_10 109.5 . . ?
C7_10 C12_10 H12C_10 109.5 . . ?
H12A_10 C12_10 H12C_10 109.5 . . ?
H12B_10 C12_10 H12C_10 109.5 . . ?
C18_10 C13_10 C14_10 122.35(12) . . ?
C18_10 C13_10 N2_2 119.35(12) . . ?
C14_10 C13_10 N2_2 118.21(12) . . ?
C15_10 C14_10 C13_10 117.64(13) . . ?
C15_10 C14_10 C20_10 121.18(13) . . ?
C13_10 C14_10 C20_10 121.10(12) . . ?
C16_10 C15_10 C14_10 121.79(13) . . ?
C16_10 C15_10 H15_10 119.1 . . ?
C14_10 C15_10 H15_10 119.1 . . ?
C15_10 C16_10 C17_10 118.87(13) . . ?
C15_10 C16_10 C21_10 120.71(14) . . ?
C17_10 C16_10 C21_10 120.42(14) . . ?
C16_10 C17_10 C18_10 121.55(14) . . ?
C16_10 C17_10 H17_10 119.2 . . ?
C18_10 C17_10 H17_10 119.2 . . ?
C13_10 C18_10 C17_10 117.71(13) . . ?
C13_10 C18_10 C19_10 121.45(12) . . ?
C17_10 C18_10 C19_10 120.83(13) . . ?
C18_10 C19_10 H19A_10 109.5 . . ?
C18_10 C19_10 H19B_10 109.5 . . ?
H19A_10 C19_10 H19B_10 109.5 . . ?
C18_10 C19_10 H19C_10 109.5 . . ?
H19A_10 C19_10 H19C_10 109.5 . . ?
H19B_10 C19_10 H19C_10 109.5 . . ?
C14_10 C20_10 H20A_10 109.5 . . ?
C14_10 C20_10 H20B_10 109.5 . . ?
H20A_10 C20_10 H20B_10 109.5 . . ?
C14_10 C20_10 H20C_10 109.5 . . ?
H20A_10 C20_10 H20C_10 109.5 . . ?
H20B_10 C20_10 H20C_10 109.5 . . ?
C16_10 C21_10 H21A_10 109.5 . . ?
C16_10 C21_10 H21B_10 109.5 . . ?
H21A_10 C21_10 H21B_10 109.5 . . ?
C16_10 C21_10 H21C_10 109.5 . . ?
H21A_10 C21_10 H21C_10 109.5 . . ?
H21B_10 C21_10 H21C_10 109.5 . . ?
N2_1 C1_11 N1_1 102.27(10) . . ?
N2_1 C1_11 Ni1_12 127.98(10) . . ?
N1_1 C1_11 Ni1_12 129.71(10) . . ?
C3_11 C2_11 N1_1 106.59(12) . . ?
C3_11 C2_11 H2_11 126.7 . . ?
N1_1 C2_11 H2_11 126.7 . . ?
C2_11 C3_11 N2_1 106.70(12) . . ?
C2_11 C3_11 H3_11 126.7 . . ?
N2_1 C3_11 H3_11 126.7 . . ?
C5_11 C4_11 C9_11 122.24(13) . . ?
C5_11 C4_11 N1_1 118.70(12) . . ?
C9_11 C4_11 N1_1 118.90(12) . . ?
C4_11 C5_11 C6_11 117.56(13) . . ?
C4_11 C5_11 C10_11 121.10(13) . . ?
C6_11 C5_11 C10_11 121.33(14) . . ?
C7_11 C6_11 C5_11 122.15(14) . . ?
C7_11 C6_11 H6_11 118.9 . . ?
C5_11 C6_11 H6_11 118.9 . . ?
C6_11 C7_11 C8_11 118.42(13) . . ?
C6_11 C7_11 C11_11 120.68(14) . . ?
C8_11 C7_11 C11_11 120.88(14) . . ?
C7_11 C8_11 C9_11 121.59(13) . . ?
C7_11 C8_11 H8_11 119.2 . . ?
C9_11 C8_11 H8_11 119.2 . . ?
C4_11 C9_11 C8_11 118.02(13) . . ?
C4_11 C9_11 C12_11 121.06(13) . . ?
C8_11 C9_11 C12_11 120.90(13) . . ?
C5_11 C10_11 H10A_11 109.5 . . ?
C5_11 C10_11 H10B_11 109.5 . . ?
H10A_11 C10_11 H10B_11 109.5 . . ?
C5_11 C10_11 H10C_11 109.5 . . ?
H10A_11 C10_11 H10C_11 109.5 . . ?
H10B_11 C10_11 H10C_11 109.5 . . ?
C7_11 C11_11 H11A_11 109.5 . . ?
C7_11 C11_11 H11B_11 109.5 . . ?
H11A_11 C11_11 H11B_11 109.5 . . ?
C7_11 C11_11 H11C_11 109.5 . . ?
H11A_11 C11_11 H11C_11 109.5 . . ?
H11B_11 C11_11 H11C_11 109.5 . . ?
C9_11 C12_11 H12A_11 109.5 . . ?
C9_11 C12_11 H12B_11 109.5 . . ?
H12A_11 C12_11 H12B_11 109.5 . . ?
C9_11 C12_11 H12C_11 109.5 . . ?
H12A_11 C12_11 H12C_11 109.5 . . ?
H12B_11 C12_11 H12C_11 109.5 . . ?
C18_11 C13_11 C14_11 122.24(12) . . ?
C18_11 C13_11 N2_1 118.99(12) . . ?
C14_11 C13_11 N2_1 118.71(12) . . ?
C15_11 C14_11 C13_11 117.84(13) . . ?
C15_11 C14_11 C20_11 119.83(13) . . ?
C13_11 C14_11 C20_11 122.32(13) . . ?
C14_11 C15_11 C16_11 121.79(13) . . ?
C14_11 C15_11 H15_11 119.1 . . ?
C16_11 C15_11 H15_11 119.1 . . ?
C15_11 C16_11 C17_11 118.63(13) . . ?
C15_11 C16_11 C21_11 120.38(13) . . ?
C17_11 C16_11 C21_11 120.99(13) . . ?
C16_11 C17_11 C18_11 121.80(13) . . ?
C16_11 C17_11 H17_11 119.1 . . ?
C18_11 C17_11 H17_11 119.1 . . ?
C17_11 C18_11 C13_11 117.63(12) . . ?
C17_11 C18_11 C19_11 120.87(13) . . ?
C13_11 C18_11 C19_11 121.50(12) . . ?
C18_11 C19_11 H19A_11 109.5 . . ?
C18_11 C19_11 H19B_11 109.5 . . ?
H19A_11 C19_11 H19B_11 109.5 . . ?
C18_11 C19_11 H19C_11 109.5 . . ?
H19A_11 C19_11 H19C_11 109.5 . . ?
H19B_11 C19_11 H19C_11 109.5 . . ?
C14_11 C20_11 H20A_11 109.5 . . ?
C14_11 C20_11 H20B_11 109.5 . . ?
H20A_11 C20_11 H20B_11 109.5 . . ?
C14_11 C20_11 H20C_11 109.5 . . ?
H20A_11 C20_11 H20C_11 109.5 . . ?
H20B_11 C20_11 H20C_11 109.5 . . ?
C16_11 C21_11 H21A_11 109.5 . . ?
C16_11 C21_11 H21B_11 109.5 . . ?
H21A_11 C21_11 H21B_11 109.5 . . ?
C16_11 C21_11 H21C_11 109.5 . . ?
H21A_11 C21_11 H21C_11 109.5 . . ?
H21B_11 C21_11 H21C_11 109.5 . . ?
C6A_12 C1A_12 C2A_12 107.9(5) . . ?
C6A_12 C1A_12 Ni1_12 123.3(6) . . ?
C2A_12 C1A_12 Ni1_12 128.8(6) . . ?
F1A_12 C2A_12 C3A_12 118.0(8) . . ?
F1A_12 C2A_12 C1A_12 117.4(7) . . ?
C3A_12 C2A_12 C1A_12 124.4(6) . . ?
C4A_12 C3A_12 C2A_12 125.0(6) . . ?
C4A_12 C3A_12 F2A_12 120.9(9) . . ?
C2A_12 C3A_12 F2A_12 114.1(10) . . ?
C3A_12 C4A_12 C5A_12 111.3(4) . . ?
C3A_12 C4A_12 H4A_12 124.4 . . ?
C5A_12 C4A_12 H4A_12 124.4 . . ?
C6A_12 C5A_12 C4A_12 125.7(6) . . ?
C6A_12 C5A_12 F3A_12 122.4(12) . . ?
C4A_12 C5A_12 F3A_12 111.9(12) . . ?
C5A_12 C6A_12 C1A_12 125.6(6) . . ?
C5A_12 C6A_12 H6A_12 117.2 . . ?
C1A_12 C6A_12 H6A_12 117.2 . . ?
C2B_12 C1B_12 C6B_12 120.0 . . ?
C2B_12 C1B_12 Ni1_12 117.4(5) . . ?
C6B_12 C1B_12 Ni1_12 122.6(5) . . ?
C1B_12 C2B_12 C3B_12 120.0 . . ?
C1B_12 C2B_12 H2B_12 120.0 . . ?
C3B_12 C2B_12 H2B_12 120.0 . . ?
F2B_12 C3B_12 C4B_12 117.6(8) . . ?
F2B_12 C3B_12 C2B_12 122.4(8) . . ?
C4B_12 C3B_12 C2B_12 120.0 . . ?
C3B_12 C4B_12 C5B_12 120.0 . . ?
C3B_12 C4B_12 H4B_12 120.0 . . ?
C5B_12 C4B_12 H4B_12 120.0 . . ?
F3B_12 C5B_12 C4B_12 123.8(11) . . ?
F3B_12 C5B_12 C6B_12 116.2(11) . . ?
C4B_12 C5B_12 C6B_12 120.0 . . ?
F1B_12 C6B_12 C5B_12 120.5(8) . . ?
F1B_12 C6B_12 C1B_12 119.5(8) . . ?
C5B_12 C6B_12 C1B_12 120.0 . . ?
C1A_12 Ni1_12 C1_10 98.9(4) . . ?
C1A_12 Ni1_12 C1_11 101.6(4) . . ?
C1_10 Ni1_12 C1_11 159.51(5) . . ?
C1_10 Ni1_12 C1B_12 99.6(3) . . ?
C1_11 Ni1_12 C1B_12 100.9(3) . . ?

_refine_diff_density_max         0.394
_refine_diff_density_min         -0.401
_refine_diff_density_rms         0.056

####################################################################### 
# 
# 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_Compound_5
_database_code_depnum_ccdc_archive 'CCDC 2017696'
loop_
_audit_author_name
_audit_author_address
'Udo Radius'
;University Wuerzburg
Germany
;
_audit_update_record             
;
2020-07-20 deposited with the CCDC.	2020-10-06 downloaded from the CCDC.
;


_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C48 H49 F5 N4 Ni'
_chemical_formula_sum            'C48 H49 F5 N4 Ni'
_chemical_formula_weight         835.62

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-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                   20.0814(16)
_cell_length_b                   18.4603(14)
_cell_length_c                   22.7528(18)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     8434.7(11)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9922
_cell_measurement_theta_min      2.21
_cell_measurement_theta_max      26.02

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.316
_exptl_crystal_F_000             3504
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.312
_exptl_crystal_size_mid          0.274
_exptl_crystal_size_min          0.196
_exptl_absorpt_coefficient_mu    0.521

_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6915
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_process_details   'SADABS 2014/5'

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'rotating anode'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            67305
_diffrn_reflns_av_unetI/netI     0.0406
_diffrn_reflns_av_R_equivalents  0.0631
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         1.745
_diffrn_reflns_theta_max         26.787
_diffrn_reflns_theta_full        26.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             8981
_reflns_number_gt                6748
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX3 v2016.5-0'
_computing_cell_refinement       'Bruker SAINT+ Integration Engine V8.37A'
_computing_data_reduction        'Bruker SAINT+ Integration Engine V8.37A'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0424P)²+11.4823P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         8981
_refine_ls_number_parameters     535
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0724
_refine_ls_R_factor_gt           0.0463
_refine_ls_wR_factor_ref         0.1166
_refine_ls_wR_factor_gt          0.1023
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.039
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Ni1 Ni 0.61917(2) 0.59486(2) 0.72470(2) 0.01544(9) Uani 1 1 d . . . . .
N1 N 0.69464(10) 0.49566(11) 0.80595(8) 0.0209(5) Uani 1 1 d . . . . .
F1 F 0.69855(7) 0.64634(8) 0.72610(6) 0.0244(3) Uani 1 1 d . . . . .
C1 C 0.53882(13) 0.54092(13) 0.72402(11) 0.0232(5) Uani 1 1 d . . . . .
C2 C 0.50922(16) 0.51404(15) 0.67415(13) 0.0343(7) Uani 1 1 d . . . . .
F2 F 0.53675(10) 0.52845(9) 0.62118(7) 0.0463(5) Uani 1 1 d . . . . .
N2 N 0.69778(10) 0.46276(11) 0.71587(8) 0.0186(4) Uani 1 1 d . . . . .
F3 F 0.42628(13) 0.44628(12) 0.62408(11) 0.0813(8) Uani 1 1 d . . . . .
N3 N 0.58158(11) 0.71862(11) 0.64646(9) 0.0221(5) Uani 1 1 d . . . . .
C3 C 0.45119(18) 0.47132(17) 0.67515(17) 0.0492(9) Uani 1 1 d . . . . .
C4 C 0.42131(17) 0.45383(18) 0.72725(19) 0.0519(10) Uani 1 1 d . . . . .
H4 H 0.3824 0.4246 0.7284 0.062 Uiso 1 1 calc R U . . .
F4 F 0.42117(9) 0.46296(11) 0.83027(10) 0.0592(6) Uani 1 1 d . . . . .
N4 N 0.52947(11) 0.72024(11) 0.72842(9) 0.0224(5) Uani 1 1 d . . . . .
C5 C 0.44928(15) 0.47973(17) 0.77738(16) 0.0424(8) Uani 1 1 d . . . . .
F5 F 0.52852(8) 0.54626(8) 0.82789(7) 0.0321(4) Uani 1 1 d . . . . .
C6 C 0.50517(13) 0.52255(14) 0.77616(13) 0.0274(6) Uani 1 1 d . . . . .
C7 C 0.66946(12) 0.51272(13) 0.75184(10) 0.0169(5) Uani 1 1 d . . . . .
C8 C 0.73921(14) 0.41597(15) 0.74661(11) 0.0288(6) Uani 1 1 d . . . . .
H8 H 0.7640 0.3767 0.7308 0.035 Uiso 1 1 calc R U . . .
C9 C 0.73738(14) 0.43689(16) 0.80269(11) 0.0308(6) Uani 1 1 d . . . . .
H9 H 0.7610 0.4155 0.8344 0.037 Uiso 1 1 calc R U . . .
C12 C 0.70352(13) 0.48335(14) 0.55396(10) 0.0229(5) Uani 1 1 d . . . . .
H12 H 0.7271 0.5100 0.5250 0.027 Uiso 1 1 calc R U . . .
C11 C 0.71910(12) 0.49431(13) 0.61309(10) 0.0188(5) Uani 1 1 d . . . . .
C10 C 0.68336(12) 0.45410(13) 0.65417(10) 0.0171(5) Uani 1 1 d . . . . .
C13 C 0.65482(13) 0.43492(15) 0.53612(11) 0.0254(6) Uani 1 1 d . . . . .
C15 C 0.63538(12) 0.40317(13) 0.63825(10) 0.0203(5) Uani 1 1 d . . . . .
C14 C 0.62203(13) 0.39439(14) 0.57870(11) 0.0237(5) Uani 1 1 d . . . . .
H14 H 0.5897 0.3598 0.5668 0.028 Uiso 1 1 calc R U . . .
C16 C 0.77296(13) 0.54611(14) 0.63097(11) 0.0239(5) Uani 1 1 d . . . . .
H16A H 0.7937 0.5668 0.5958 0.036 Uiso 1 1 calc R U . . .
H16B H 0.8067 0.5203 0.6540 0.036 Uiso 1 1 calc R U . . .
H16C H 0.7537 0.5851 0.6548 0.036 Uiso 1 1 calc R U . . .
C17 C 0.63695(15) 0.4274(2) 0.47196(11) 0.0410(8) Uani 1 1 d . . . . .
H17A H 0.6715 0.4502 0.4478 0.061 Uiso 1 1 calc R U . . .
H17B H 0.5941 0.4510 0.4646 0.061 Uiso 1 1 calc R U . . .
H17C H 0.6337 0.3759 0.4618 0.061 Uiso 1 1 calc R U . . .
C18 C 0.59870(14) 0.35942(14) 0.68392(12) 0.0276(6) Uani 1 1 d . . . . .
H18A H 0.5627 0.3321 0.6650 0.041 Uiso 1 1 calc R U . . .
H18B H 0.5799 0.3920 0.7136 0.041 Uiso 1 1 calc R U . . .
H18C H 0.6297 0.3257 0.7028 0.041 Uiso 1 1 calc R U . . .
C19 C 0.67610(12) 0.52613(14) 0.86228(10) 0.0200(5) Uani 1 1 d . . . . .
C20 C 0.70841(12) 0.58813(14) 0.88255(10) 0.0215(5) Uani 1 1 d . . . . .
C21 C 0.69016(13) 0.61389(15) 0.93783(11) 0.0242(6) Uani 1 1 d . . . . .
H21 H 0.7106 0.6567 0.9524 0.029 Uiso 1 1 calc R U . . .
C22 C 0.64290(13) 0.57888(14) 0.97230(10) 0.0240(6) Uani 1 1 d . . . . .
C23 C 0.61374(13) 0.51645(14) 0.95115(10) 0.0239(5) Uani 1 1 d . . . . .
H23 H 0.5819 0.4919 0.9747 0.029 Uiso 1 1 calc R U . . .
C24 C 0.62982(13) 0.48848(14) 0.89594(10) 0.0218(5) Uani 1 1 d . . . . .
C25 C 0.76247(14) 0.62391(17) 0.84720(11) 0.0300(6) Uani 1 1 d . . . . .
H25A H 0.7450 0.6372 0.8084 0.045 Uiso 1 1 calc R U . . .
H25B H 0.7999 0.5903 0.8425 0.045 Uiso 1 1 calc R U . . .
H25C H 0.7777 0.6676 0.8676 0.045 Uiso 1 1 calc R U . . .
C26 C 0.62502(15) 0.60821(16) 1.03220(11) 0.0329(7) Uani 1 1 d . . . . .
H26A H 0.6154 0.6601 1.0291 0.049 Uiso 1 1 calc R U . . .
H26B H 0.6624 0.6007 1.0592 0.049 Uiso 1 1 calc R U . . .
H26C H 0.5856 0.5828 1.0471 0.049 Uiso 1 1 calc R U . . .
C27 C 0.59737(15) 0.41933(15) 0.87485(12) 0.0293(6) Uani 1 1 d . . . . .
H27A H 0.5918 0.4213 0.8321 0.044 Uiso 1 1 calc R U . . .
H27B H 0.5537 0.4140 0.8936 0.044 Uiso 1 1 calc R U . . .
H27C H 0.6256 0.3779 0.8852 0.044 Uiso 1 1 calc R U . . .
C28 C 0.57418(12) 0.68018(13) 0.69718(10) 0.0182(5) Uani 1 1 d . . . . .
C29 C 0.51005(16) 0.78182(15) 0.69795(12) 0.0343(7) Uani 1 1 d . . . . .
H29 H 0.4795 0.8178 0.7109 0.041 Uiso 1 1 calc R U . . .
C30 C 0.54265(15) 0.78066(15) 0.64681(13) 0.0354(7) Uani 1 1 d . . . . .
H30 H 0.5397 0.8158 0.6164 0.042 Uiso 1 1 calc R U . . .
C31 C 0.62573(12) 0.70307(13) 0.59772(10) 0.0178(5) Uani 1 1 d . . . . .
C32 C 0.69082(13) 0.72948(13) 0.59966(10) 0.0214(5) Uani 1 1 d . . . . .
C33 C 0.73180(13) 0.71727(15) 0.55141(11) 0.0289(6) Uani 1 1 d . . . . .
H33 H 0.7765 0.7341 0.5525 0.035 Uiso 1 1 calc R U . . .
C34 C 0.70940(15) 0.68147(16) 0.50212(11) 0.0307(6) Uani 1 1 d . . . . .
C35 C 0.64389(16) 0.65913(15) 0.50029(11) 0.0312(7) Uani 1 1 d . . . . .
H35 H 0.6280 0.6355 0.4660 0.037 Uiso 1 1 calc R U . . .
C36 C 0.60010(13) 0.67002(14) 0.54726(11) 0.0254(6) Uani 1 1 d . . . . .
C37 C 0.71508(16) 0.77435(16) 0.65044(11) 0.0340(7) Uani 1 1 d . . . . .
H37A H 0.7591 0.7941 0.6412 0.051 Uiso 1 1 calc R U . . .
H37B H 0.7181 0.7440 0.6857 0.051 Uiso 1 1 calc R U . . .
H37C H 0.6839 0.8142 0.6576 0.051 Uiso 1 1 calc R U . . .
C38 C 0.75652(18) 0.6676(2) 0.45127(13) 0.0508(9) Uani 1 1 d . . . . .
H38A H 0.7348 0.6813 0.4143 0.076 Uiso 1 1 calc R U . . .
H38B H 0.7682 0.6161 0.4501 0.076 Uiso 1 1 calc R U . . .
H38C H 0.7970 0.6965 0.4565 0.076 Uiso 1 1 calc R U . . .
C39 C 0.52773(16) 0.65036(19) 0.54033(14) 0.0445(8) Uani 1 1 d . . . . .
H39A H 0.5060 0.6856 0.5145 0.067 Uiso 1 1 calc R U . . .
H39B H 0.5060 0.6508 0.5789 0.067 Uiso 1 1 calc R U . . .
H39C H 0.5241 0.6019 0.5231 0.067 Uiso 1 1 calc R U . . .
C40 C 0.50700(13) 0.70527(13) 0.78761(10) 0.0199(5) Uani 1 1 d . . . . .
C41 C 0.54974(13) 0.72088(13) 0.83426(11) 0.0220(5) Uani 1 1 d . . . . .
C42 C 0.52619(13) 0.70883(14) 0.89101(11) 0.0243(6) Uani 1 1 d . . . . .
H42 H 0.5545 0.7187 0.9235 0.029 Uiso 1 1 calc R U . . .
C43 C 0.46231(14) 0.68276(14) 0.90130(11) 0.0241(6) Uani 1 1 d . . . . .
C44 C 0.42098(13) 0.66942(13) 0.85341(11) 0.0227(5) Uani 1 1 d . . . . .
H44 H 0.3771 0.6522 0.8602 0.027 Uiso 1 1 calc R U . . .
C45 C 0.44214(13) 0.68059(13) 0.79598(11) 0.0209(5) Uani 1 1 d . . . . .
C46 C 0.61868(13) 0.75113(15) 0.82430(13) 0.0305(6) Uani 1 1 d . . . . .
H46A H 0.6443 0.7177 0.7996 0.046 Uiso 1 1 calc R U . . .
H46B H 0.6412 0.7571 0.8622 0.046 Uiso 1 1 calc R U . . .
H46C H 0.6153 0.7982 0.8046 0.046 Uiso 1 1 calc R U . . .
C47 C 0.43793(16) 0.66905(18) 0.96325(12) 0.0366(7) Uani 1 1 d . . . . .
H47A H 0.4015 0.6338 0.9624 0.055 Uiso 1 1 calc R U . . .
H47B H 0.4220 0.7145 0.9804 0.055 Uiso 1 1 calc R U . . .
H47C H 0.4746 0.6500 0.9871 0.055 Uiso 1 1 calc R U . . .
C48 C 0.39564(14) 0.66569(15) 0.74509(12) 0.0280(6) Uani 1 1 d . . . . .
H48A H 0.3849 0.7113 0.7252 0.042 Uiso 1 1 calc R U . . .
H48B H 0.3546 0.6434 0.7598 0.042 Uiso 1 1 calc R U . . .
H48C H 0.4173 0.6327 0.7173 0.042 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 F1 1.8560(15) . ?
Ni1 C1 1.896(3) . ?
Ni1 C28 1.921(2) . ?
Ni1 C7 1.924(2) . ?
N1 C7 1.368(3) . ?
N1 C9 1.385(3) . ?
N1 C19 1.448(3) . ?
C1 C2 1.374(4) . ?
C1 C6 1.407(4) . ?
C2 F2 1.352(4) . ?
C2 C3 1.407(5) . ?
N2 C7 1.358(3) . ?
N2 C8 1.388(3) . ?
N2 C10 1.442(3) . ?
F3 C3 1.347(4) . ?
N3 C28 1.363(3) . ?
N3 C30 1.387(3) . ?
N3 C31 1.448(3) . ?
C3 C4 1.367(5) . ?
C4 C5 1.358(5) . ?
C4 H4 0.9500 . ?
F4 C5 1.365(4) . ?
N4 C28 1.363(3) . ?
N4 C29 1.387(3) . ?
N4 C40 1.447(3) . ?
C5 C6 1.373(4) . ?
F5 C6 1.340(3) . ?
C8 C9 1.334(4) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
C12 C13 1.386(4) . ?
C12 C11 1.396(3) . ?
C12 H12 0.9500 . ?
C11 C10 1.393(3) . ?
C11 C16 1.500(3) . ?
C10 C15 1.394(3) . ?
C13 C14 1.390(4) . ?
C13 C17 1.510(3) . ?
C15 C14 1.391(3) . ?
C15 C18 1.508(3) . ?
C14 H14 0.9500 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 C24 1.391(4) . ?
C19 C20 1.394(4) . ?
C20 C21 1.394(3) . ?
C20 C25 1.504(4) . ?
C21 C22 1.390(4) . ?
C21 H21 0.9500 . ?
C22 C23 1.379(4) . ?
C22 C26 1.510(3) . ?
C23 C24 1.396(3) . ?
C23 H23 0.9500 . ?
C24 C27 1.511(4) . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C29 C30 1.335(4) . ?
C29 H29 0.9500 . ?
C30 H30 0.9500 . ?
C31 C32 1.396(3) . ?
C31 C36 1.398(3) . ?
C32 C33 1.390(3) . ?
C32 C37 1.503(3) . ?
C33 C34 1.377(4) . ?
C33 H33 0.9500 . ?
C34 C35 1.379(4) . ?
C34 C38 1.516(4) . ?
C35 C36 1.398(4) . ?
C35 H35 0.9500 . ?
C36 C39 1.506(4) . ?
C37 H37A 0.9800 . ?
C37 H37B 0.9800 . ?
C37 H37C 0.9800 . ?
C38 H38A 0.9800 . ?
C38 H38B 0.9800 . ?
C38 H38C 0.9800 . ?
C39 H39A 0.9800 . ?
C39 H39B 0.9800 . ?
C39 H39C 0.9800 . ?
C40 C45 1.393(4) . ?
C40 C41 1.395(4) . ?
C41 C42 1.393(3) . ?
C41 C46 1.510(4) . ?
C42 C43 1.390(4) . ?
C42 H42 0.9500 . ?
C43 C44 1.392(4) . ?
C43 C47 1.514(3) . ?
C44 C45 1.389(3) . ?
C44 H44 0.9500 . ?
C45 C48 1.513(4) . ?
C46 H46A 0.9800 . ?
C46 H46B 0.9800 . ?
C46 H46C 0.9800 . ?
C47 H47A 0.9800 . ?
C47 H47B 0.9800 . ?
C47 H47C 0.9800 . ?
C48 H48A 0.9800 . ?
C48 H48B 0.9800 . ?
C48 H48C 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
F1 Ni1 C1 178.98(9) . . ?
F1 Ni1 C28 89.41(8) . . ?
C1 Ni1 C28 91.59(10) . . ?
F1 Ni1 C7 86.97(8) . . ?
C1 Ni1 C7 92.03(10) . . ?
C28 Ni1 C7 176.36(10) . . ?
C7 N1 C9 111.17(19) . . ?
C7 N1 C19 127.7(2) . . ?
C9 N1 C19 120.7(2) . . ?
C2 C1 C6 113.7(3) . . ?
C2 C1 Ni1 124.4(2) . . ?
C6 C1 Ni1 121.91(19) . . ?
F2 C2 C1 119.2(3) . . ?
F2 C2 C3 117.6(3) . . ?
C1 C2 C3 123.2(3) . . ?
C7 N2 C8 111.7(2) . . ?
C7 N2 C10 125.3(2) . . ?
C8 N2 C10 122.8(2) . . ?
C28 N3 C30 111.3(2) . . ?
C28 N3 C31 127.7(2) . . ?
C30 N3 C31 120.9(2) . . ?
F3 C3 C4 120.3(3) . . ?
F3 C3 C2 119.1(4) . . ?
C4 C3 C2 120.6(3) . . ?
C5 C4 C3 117.6(3) . . ?
C5 C4 H4 121.2 . . ?
C3 C4 H4 121.2 . . ?
C28 N4 C29 111.7(2) . . ?
C28 N4 C40 125.9(2) . . ?
C29 N4 C40 122.3(2) . . ?
C4 C5 F4 119.3(3) . . ?
C4 C5 C6 121.6(3) . . ?
F4 C5 C6 119.1(3) . . ?
F5 C6 C5 117.1(3) . . ?
F5 C6 C1 119.6(2) . . ?
C5 C6 C1 123.3(3) . . ?
N2 C7 N1 103.4(2) . . ?
N2 C7 Ni1 124.18(17) . . ?
N1 C7 Ni1 131.65(17) . . ?
C9 C8 N2 106.6(2) . . ?
C9 C8 H8 126.7 . . ?
N2 C8 H8 126.7 . . ?
C8 C9 N1 107.2(2) . . ?
C8 C9 H9 126.4 . . ?
N1 C9 H9 126.4 . . ?
C13 C12 C11 122.3(2) . . ?
C13 C12 H12 118.9 . . ?
C11 C12 H12 118.9 . . ?
C10 C11 C12 117.0(2) . . ?
C10 C11 C16 122.0(2) . . ?
C12 C11 C16 121.0(2) . . ?
C11 C10 C15 122.8(2) . . ?
C11 C10 N2 119.4(2) . . ?
C15 C10 N2 117.8(2) . . ?
C12 C13 C14 118.5(2) . . ?
C12 C13 C17 120.7(2) . . ?
C14 C13 C17 120.8(2) . . ?
C14 C15 C10 117.7(2) . . ?
C14 C15 C18 121.0(2) . . ?
C10 C15 C18 121.3(2) . . ?
C13 C14 C15 121.7(2) . . ?
C13 C14 H14 119.2 . . ?
C15 C14 H14 119.2 . . ?
C11 C16 H16A 109.5 . . ?
C11 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C11 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C13 C17 H17A 109.5 . . ?
C13 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C13 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C15 C18 H18A 109.5 . . ?
C15 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C15 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C24 C19 C20 122.6(2) . . ?
C24 C19 N1 117.7(2) . . ?
C20 C19 N1 119.5(2) . . ?
C21 C20 C19 117.1(2) . . ?
C21 C20 C25 121.5(2) . . ?
C19 C20 C25 121.3(2) . . ?
C22 C21 C20 122.0(2) . . ?
C22 C21 H21 119.0 . . ?
C20 C21 H21 119.0 . . ?
C23 C22 C21 118.8(2) . . ?
C23 C22 C26 120.9(2) . . ?
C21 C22 C26 120.3(2) . . ?
C22 C23 C24 121.7(2) . . ?
C22 C23 H23 119.2 . . ?
C24 C23 H23 119.2 . . ?
C19 C24 C23 117.7(2) . . ?
C19 C24 C27 122.4(2) . . ?
C23 C24 C27 119.9(2) . . ?
C20 C25 H25A 109.5 . . ?
C20 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C20 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C22 C26 H26A 109.5 . . ?
C22 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C22 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C24 C27 H27A 109.5 . . ?
C24 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C24 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
N3 C28 N4 103.3(2) . . ?
N3 C28 Ni1 130.68(18) . . ?
N4 C28 Ni1 125.78(17) . . ?
C30 C29 N4 106.5(2) . . ?
C30 C29 H29 126.7 . . ?
N4 C29 H29 126.7 . . ?
C29 C30 N3 107.1(2) . . ?
C29 C30 H30 126.4 . . ?
N3 C30 H30 126.4 . . ?
C32 C31 C36 121.5(2) . . ?
C32 C31 N3 118.7(2) . . ?
C36 C31 N3 119.3(2) . . ?
C33 C32 C31 118.2(2) . . ?
C33 C32 C37 120.3(2) . . ?
C31 C32 C37 121.4(2) . . ?
C34 C33 C32 121.8(3) . . ?
C34 C33 H33 119.1 . . ?
C32 C33 H33 119.1 . . ?
C33 C34 C35 118.7(2) . . ?
C33 C34 C38 119.9(3) . . ?
C35 C34 C38 121.4(3) . . ?
C34 C35 C36 122.3(2) . . ?
C34 C35 H35 118.9 . . ?
C36 C35 H35 118.9 . . ?
C35 C36 C31 117.3(2) . . ?
C35 C36 C39 119.5(3) . . ?
C31 C36 C39 123.1(3) . . ?
C32 C37 H37A 109.5 . . ?
C32 C37 H37B 109.5 . . ?
H37A C37 H37B 109.5 . . ?
C32 C37 H37C 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?
C34 C38 H38A 109.5 . . ?
C34 C38 H38B 109.5 . . ?
H38A C38 H38B 109.5 . . ?
C34 C38 H38C 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?
C36 C39 H39A 109.5 . . ?
C36 C39 H39B 109.5 . . ?
H39A C39 H39B 109.5 . . ?
C36 C39 H39C 109.5 . . ?
H39A C39 H39C 109.5 . . ?
H39B C39 H39C 109.5 . . ?
C45 C40 C41 122.6(2) . . ?
C45 C40 N4 118.8(2) . . ?
C41 C40 N4 118.5(2) . . ?
C42 C41 C40 117.6(2) . . ?
C42 C41 C46 120.6(2) . . ?
C40 C41 C46 121.8(2) . . ?
C43 C42 C41 121.6(2) . . ?
C43 C42 H42 119.2 . . ?
C41 C42 H42 119.2 . . ?
C42 C43 C44 118.7(2) . . ?
C42 C43 C47 120.9(2) . . ?
C44 C43 C47 120.4(2) . . ?
C45 C44 C43 121.9(2) . . ?
C45 C44 H44 119.1 . . ?
C43 C44 H44 119.1 . . ?
C44 C45 C40 117.6(2) . . ?
C44 C45 C48 120.3(2) . . ?
C40 C45 C48 122.1(2) . . ?
C41 C46 H46A 109.5 . . ?
C41 C46 H46B 109.5 . . ?
H46A C46 H46B 109.5 . . ?
C41 C46 H46C 109.5 . . ?
H46A C46 H46C 109.5 . . ?
H46B C46 H46C 109.5 . . ?
C43 C47 H47A 109.5 . . ?
C43 C47 H47B 109.5 . . ?
H47A C47 H47B 109.5 . . ?
C43 C47 H47C 109.5 . . ?
H47A C47 H47C 109.5 . . ?
H47B C47 H47C 109.5 . . ?
C45 C48 H48A 109.5 . . ?
C45 C48 H48B 109.5 . . ?
H48A C48 H48B 109.5 . . ?
C45 C48 H48C 109.5 . . ?
H48A C48 H48C 109.5 . . ?
H48B C48 H48C 109.5 . . ?

_refine_diff_density_max         0.499
_refine_diff_density_min         -0.526
_refine_diff_density_rms         0.066

####################################################################### 
# 
# 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_Compound_11
_database_code_depnum_ccdc_archive 'CCDC 2017700'
loop_
_audit_author_name
_audit_author_address
'Udo Radius'
;University Wuerzburg
Germany
;
_audit_update_record             
;
2020-07-20 deposited with the CCDC.	2020-10-06 downloaded from the CCDC.
;


_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C48 H48 F5 N4 Ni'
_chemical_formula_sum            'C48 H48 F5 N4 Ni'
_chemical_formula_weight         834.61

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ni Ni -3.0029 0.5091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'I 2/a'
_space_group_name_Hall           '-I 2ya'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   17.3579(3)
_cell_length_b                   13.3131(2)
_cell_length_c                   19.0795(3)
_cell_angle_alpha                90
_cell_angle_beta                 105.933(2)
_cell_angle_gamma                90
_cell_volume                     4239.65(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    16952
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      77.3600
_cell_measurement_theta_min      4.1000

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.308
_exptl_crystal_F_000             1748
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.195
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.088
_exptl_absorpt_coefficient_mu    1.159
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.67153
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.45a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100.00(10)
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            25553
_diffrn_reflns_av_unetI/netI     0.0185
_diffrn_reflns_av_R_equivalents  0.0364
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         4.103
_diffrn_reflns_theta_max         77.702
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4419
_reflns_number_gt                4147
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_cell_refinement       'CrysAlisPro 1.171.40.45a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.45a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.45a (Rigaku OD, 2019)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0523P)²+5.7440P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4419
_refine_ls_number_parameters     270
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0430
_refine_ls_R_factor_gt           0.0400
_refine_ls_wR_factor_ref         0.1096
_refine_ls_wR_factor_gt          0.1067
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_restrained_S_all      1.083
_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 0.750000 0.28719(3) 0.500000 0.01853(12) Uani 1 2 d S T P . .
N1 N 0.64500(8) 0.31077(10) 0.59858(7) 0.0225(3) Uani 1 1 d . . . . .
N2 N 0.60243(8) 0.19226(10) 0.52212(7) 0.0229(3) Uani 1 1 d . . . . .
F1 F 0.88011(6) 0.44771(7) 0.58303(5) 0.0291(2) Uani 1 1 d . . . . .
F2 F 0.87822(7) 0.64922(9) 0.58393(7) 0.0458(3) Uani 1 1 d . . . . .
F3 F 0.750000 0.75161(12) 0.500000 0.0590(6) Uani 1 2 d S T P . .
C1 C 0.66306(9) 0.26112(12) 0.54220(8) 0.0207(3) Uani 1 1 d . . . . .
C2 C 0.57554(10) 0.27379(14) 0.61213(10) 0.0292(4) Uani 1 1 d . . . . .
H2 H 0.552101 0.296304 0.647614 0.035 Uiso 1 1 calc R U . . .
C3 C 0.54882(10) 0.19938(14) 0.56415(10) 0.0299(4) Uani 1 1 d . . . . .
H3 H 0.503359 0.160297 0.559899 0.036 Uiso 1 1 calc R U . . .
C4 C 0.69118(9) 0.39167(12) 0.63949(8) 0.0225(3) Uani 1 1 d . . . . .
C5 C 0.76829(9) 0.37209(12) 0.68404(8) 0.0234(3) Uani 1 1 d . . . . .
C6 C 0.81042(10) 0.45186(13) 0.72393(9) 0.0265(3) Uani 1 1 d . . . . .
H6 H 0.861546 0.440293 0.754318 0.032 Uiso 1 1 calc R U . . .
C7 C 0.77878(11) 0.54802(13) 0.71993(9) 0.0289(4) Uani 1 1 d . . . . .
C8 C 0.70208(10) 0.56449(13) 0.67426(9) 0.0283(3) Uani 1 1 d . . . . .
H8 H 0.680498 0.628835 0.670834 0.034 Uiso 1 1 calc R U . . .
C9 C 0.65697(10) 0.48745(13) 0.63371(9) 0.0254(3) Uani 1 1 d . . . . .
C10 C 0.80601(10) 0.26977(13) 0.68701(9) 0.0282(3) Uani 1 1 d . . . . .
H10A H 0.820096 0.257594 0.642493 0.042 Uiso 1 1 calc R U . . .
H10B H 0.768654 0.219568 0.693065 0.042 Uiso 1 1 calc R U . . .
H10C H 0.853321 0.266927 0.727367 0.042 Uiso 1 1 calc R U . . .
C11 C 0.82632(12) 0.63369(15) 0.76249(11) 0.0410(5) Uani 1 1 d . . . . .
H11A H 0.842689 0.678293 0.729733 0.061 Uiso 1 1 calc R U . . .
H11B H 0.872826 0.607687 0.797499 0.061 Uiso 1 1 calc R U . . .
H11C H 0.793706 0.669629 0.787344 0.061 Uiso 1 1 calc R U . . .
C12 C 0.57491(10) 0.50828(15) 0.58344(10) 0.0332(4) Uani 1 1 d . . . . .
H12A H 0.570783 0.578107 0.570373 0.050 Uiso 1 1 calc R U . . .
H12B H 0.534893 0.491866 0.607716 0.050 Uiso 1 1 calc R U . . .
H12C H 0.566847 0.468130 0.540228 0.050 Uiso 1 1 calc R U . . .
C13 C 0.59635(9) 0.11679(12) 0.46660(9) 0.0230(3) Uani 1 1 d . . . . .
C14 C 0.63123(10) 0.02336(13) 0.48768(10) 0.0292(4) Uani 1 1 d . . . . .
C15 C 0.62397(11) -0.04950(13) 0.43353(11) 0.0330(4) Uani 1 1 d . . . . .
H15 H 0.646686 -0.112485 0.446258 0.040 Uiso 1 1 calc R U . . .
C16 C 0.58376(11) -0.03031(13) 0.36131(11) 0.0326(4) Uani 1 1 d . . . . .
C17 C 0.54912(11) 0.06336(13) 0.34300(10) 0.0294(4) Uani 1 1 d . . . . .
H17 H 0.521905 0.076493 0.294666 0.035 Uiso 1 1 calc R U . . .
C18 C 0.55395(10) 0.13854(12) 0.39510(9) 0.0250(3) Uani 1 1 d . . . . .
C19 C 0.67477(14) 0.00163(17) 0.56615(11) 0.0429(5) Uani 1 1 d . . . . .
H19A H 0.695328 -0.065701 0.570233 0.064 Uiso 1 1 calc R U . . .
H19B H 0.638384 0.008666 0.595720 0.064 Uiso 1 1 calc R U . . .
H19C H 0.718319 0.048093 0.582453 0.064 Uiso 1 1 calc R U . . .
C20 C 0.57717(15) -0.11043(15) 0.30387(13) 0.0467(5) Uani 1 1 d . . . . .
H20A H 0.534605 -0.093592 0.261505 0.070 Uiso 1 1 calc R U . . .
H20B H 0.565995 -0.173999 0.322723 0.070 Uiso 1 1 calc R U . . .
H20C H 0.626734 -0.114603 0.290881 0.070 Uiso 1 1 calc R U . . .
C21 C 0.51345(11) 0.23838(13) 0.37526(10) 0.0317(4) Uani 1 1 d . . . . .
H21A H 0.495592 0.244647 0.323173 0.048 Uiso 1 1 calc R U . . .
H21B H 0.550615 0.291344 0.394987 0.048 Uiso 1 1 calc R U . . .
H21C H 0.468271 0.242946 0.394953 0.048 Uiso 1 1 calc R U . . .
C22 C 0.750000 0.43661(17) 0.500000 0.0224(4) Uani 1 2 d S T P . .
C23 C 0.81298(9) 0.49396(13) 0.54053(9) 0.0249(3) Uani 1 1 d . . . . .
C24 C 0.81473(10) 0.59757(14) 0.54210(10) 0.0318(4) Uani 1 1 d . . . . .
C25 C 0.750000 0.64983(18) 0.500000 0.0364(6) Uani 1 2 d S T P . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ni1 C1 1.9269(15) 2_656 ?
Ni1 C1 1.9269(15) . ?
Ni1 C22 1.989(2) . ?
N1 C1 1.3703(19) . ?
N1 C2 1.391(2) . ?
N1 C4 1.438(2) . ?
N2 C1 1.369(2) . ?
N2 C3 1.388(2) . ?
N2 C13 1.443(2) . ?
F1 C23 1.3695(18) . ?
F2 C24 1.357(2) . ?
F3 C25 1.355(3) . ?
C2 C3 1.342(2) . ?
C2 H2 0.9300 . ?
C3 H3 0.9300 . ?
C4 C9 1.398(2) . ?
C4 C5 1.399(2) . ?
C5 C6 1.392(2) . ?
C5 C10 1.506(2) . ?
C6 C7 1.387(2) . ?
C6 H6 0.9300 . ?
C7 C8 1.394(2) . ?
C7 C11 1.508(2) . ?
C8 C9 1.390(2) . ?
C8 H8 0.9300 . ?
C9 C12 1.508(2) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 C18 1.391(2) . ?
C13 C14 1.393(2) . ?
C14 C15 1.397(3) . ?
C14 C19 1.509(3) . ?
C15 C16 1.387(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.387(3) . ?
C16 C20 1.511(2) . ?
C17 C18 1.397(2) . ?
C17 H17 0.9300 . ?
C18 C21 1.503(2) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 C23 1.383(2) 2_656 ?
C22 C23 1.383(2) . ?
C23 C24 1.380(2) . ?
C24 C25 1.377(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 Ni1 C1 159.24(9) 2_656 . ?
C1 Ni1 C22 100.38(5) 2_656 . ?
C1 Ni1 C22 100.38(5) . . ?
C1 N1 C2 111.84(13) . . ?
C1 N1 C4 125.01(13) . . ?
C2 N1 C4 123.15(13) . . ?
C1 N2 C3 112.23(13) . . ?
C1 N2 C13 124.58(13) . . ?
C3 N2 C13 123.10(13) . . ?
N2 C1 N1 102.64(12) . . ?
N2 C1 Ni1 129.34(11) . . ?
N1 C1 Ni1 127.98(11) . . ?
C3 C2 N1 106.82(14) . . ?
C3 C2 H2 126.6 . . ?
N1 C2 H2 126.6 . . ?
C2 C3 N2 106.47(14) . . ?
C2 C3 H3 126.8 . . ?
N2 C3 H3 126.8 . . ?
C9 C4 C5 122.20(15) . . ?
C9 C4 N1 118.60(14) . . ?
C5 C4 N1 119.20(14) . . ?
C6 C5 C4 117.48(15) . . ?
C6 C5 C10 120.80(15) . . ?
C4 C5 C10 121.68(15) . . ?
C7 C6 C5 122.26(15) . . ?
C7 C6 H6 118.9 . . ?
C5 C6 H6 118.9 . . ?
C6 C7 C8 118.39(16) . . ?
C6 C7 C11 121.25(16) . . ?
C8 C7 C11 120.35(17) . . ?
C9 C8 C7 121.83(16) . . ?
C9 C8 H8 119.1 . . ?
C7 C8 H8 119.1 . . ?
C8 C9 C4 117.83(15) . . ?
C8 C9 C12 120.51(16) . . ?
C4 C9 C12 121.63(15) . . ?
C5 C10 H10A 109.5 . . ?
C5 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C5 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C7 C11 H11A 109.5 . . ?
C7 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C7 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C9 C12 H12A 109.5 . . ?
C9 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C9 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C18 C13 C14 122.67(15) . . ?
C18 C13 N2 119.18(14) . . ?
C14 C13 N2 118.11(15) . . ?
C13 C14 C15 117.55(16) . . ?
C13 C14 C19 121.15(16) . . ?
C15 C14 C19 121.30(17) . . ?
C16 C15 C14 121.69(16) . . ?
C16 C15 H15 119.2 . . ?
C14 C15 H15 119.2 . . ?
C15 C16 C17 118.77(16) . . ?
C15 C16 C20 120.52(18) . . ?
C17 C16 C20 120.71(19) . . ?
C16 C17 C18 121.85(17) . . ?
C16 C17 H17 119.1 . . ?
C18 C17 H17 119.1 . . ?
C13 C18 C17 117.46(15) . . ?
C13 C18 C21 121.06(15) . . ?
C17 C18 C21 121.46(16) . . ?
C14 C19 H19A 109.5 . . ?
C14 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C14 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C16 C20 H20A 109.5 . . ?
C16 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C16 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C18 C21 H21A 109.5 . . ?
C18 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C18 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C23 C22 C23 113.0(2) 2_656 . ?
C23 C22 Ni1 123.52(10) 2_656 . ?
C23 C22 Ni1 123.52(10) . . ?
F1 C23 C24 115.24(14) . . ?
F1 C23 C22 119.77(15) . . ?
C24 C23 C22 124.99(16) . . ?
F2 C24 C25 119.20(17) . . ?
F2 C24 C23 121.92(16) . . ?
C25 C24 C23 118.87(17) . . ?
F3 C25 C24 120.35(12) . . ?
F3 C25 C24 120.35(11) . 2_656 ?
C24 C25 C24 119.3(2) . 2_656 ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C3 N2 C1 N1 0.30(18) . . . . ?
C13 N2 C1 N1 -176.47(14) . . . . ?
C3 N2 C1 Ni1 -177.28(13) . . . . ?
C13 N2 C1 Ni1 6.0(2) . . . . ?
C2 N1 C1 N2 -0.31(18) . . . . ?
C4 N1 C1 N2 179.84(14) . . . . ?
C2 N1 C1 Ni1 177.31(12) . . . . ?
C4 N1 C1 Ni1 -2.5(2) . . . . ?
C1 N1 C2 C3 0.2(2) . . . . ?
C4 N1 C2 C3 -179.93(15) . . . . ?
N1 C2 C3 N2 0.0(2) . . . . ?
C1 N2 C3 C2 -0.2(2) . . . . ?
C13 N2 C3 C2 176.65(15) . . . . ?
C1 N1 C4 C9 113.53(17) . . . . ?
C2 N1 C4 C9 -66.3(2) . . . . ?
C1 N1 C4 C5 -67.0(2) . . . . ?
C2 N1 C4 C5 113.20(18) . . . . ?
C9 C4 C5 C6 0.8(2) . . . . ?
N1 C4 C5 C6 -178.68(13) . . . . ?
C9 C4 C5 C10 -176.97(15) . . . . ?
N1 C4 C5 C10 3.5(2) . . . . ?
C4 C5 C6 C7 -0.7(2) . . . . ?
C10 C5 C6 C7 177.08(16) . . . . ?
C5 C6 C7 C8 0.0(3) . . . . ?
C5 C6 C7 C11 -178.69(16) . . . . ?
C6 C7 C8 C9 0.6(3) . . . . ?
C11 C7 C8 C9 179.34(17) . . . . ?
C7 C8 C9 C4 -0.5(2) . . . . ?
C7 C8 C9 C12 -178.55(16) . . . . ?
C5 C4 C9 C8 -0.2(2) . . . . ?
N1 C4 C9 C8 179.27(14) . . . . ?
C5 C4 C9 C12 177.81(15) . . . . ?
N1 C4 C9 C12 -2.7(2) . . . . ?
C1 N2 C13 C18 -91.39(19) . . . . ?
C3 N2 C13 C18 92.2(2) . . . . ?
C1 N2 C13 C14 90.78(19) . . . . ?
C3 N2 C13 C14 -85.7(2) . . . . ?
C18 C13 C14 C15 1.4(2) . . . . ?
N2 C13 C14 C15 179.15(14) . . . . ?
C18 C13 C14 C19 -178.25(17) . . . . ?
N2 C13 C14 C19 -0.5(2) . . . . ?
C13 C14 C15 C16 0.1(3) . . . . ?
C19 C14 C15 C16 179.73(17) . . . . ?
C14 C15 C16 C17 -0.9(3) . . . . ?
C14 C15 C16 C20 179.73(17) . . . . ?
C15 C16 C17 C18 0.3(3) . . . . ?
C20 C16 C17 C18 179.65(17) . . . . ?
C14 C13 C18 C17 -2.0(2) . . . . ?
N2 C13 C18 C17 -179.71(14) . . . . ?
C14 C13 C18 C21 176.68(15) . . . . ?
N2 C13 C18 C21 -1.0(2) . . . . ?
C16 C17 C18 C13 1.1(2) . . . . ?
C16 C17 C18 C21 -177.53(16) . . . . ?
C23 C22 C23 F1 -179.41(16) 2_656 . . . ?
Ni1 C22 C23 F1 0.59(16) . . . . ?
C23 C22 C23 C24 0.39(13) 2_656 . . . ?
Ni1 C22 C23 C24 -179.61(13) . . . . ?
F1 C23 C24 F2 -1.1(2) . . . . ?
C22 C23 C24 F2 179.14(14) . . . . ?
F1 C23 C24 C25 179.04(12) . . . . ?
C22 C23 C24 C25 -0.8(3) . . . . ?
F2 C24 C25 F3 0.45(19) . . . . ?
C23 C24 C25 F3 -179.65(12) . . . . ?
F2 C24 C25 C24 -179.55(19) . . . 2_656 ?
C23 C24 C25 C24 0.36(12) . . . 2_656 ?

_refine_diff_density_max         1.409
_refine_diff_density_min         -0.449
_refine_diff_density_rms         0.058

####################################################################### 
# 
# 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_Compound_13
_database_code_depnum_ccdc_archive 'CCDC 2017697'
loop_
_audit_author_name
_audit_author_address
'Udo Radius'
;University Wuerzburg
Germany
;
_audit_update_record             
;
2020-07-20 deposited with the CCDC.	2020-10-06 downloaded from the CCDC.
;


_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C48 H49 F4 N4 Ni'
_chemical_formula_sum            'C48 H49 F4 N4 Ni'
_chemical_formula_weight         816.62

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   21.976(3)
_cell_length_b                   13.1060(15)
_cell_length_c                   17.395(3)
_cell_angle_alpha                90
_cell_angle_beta                 122.824(3)
_cell_angle_gamma                90
_cell_volume                     4210.2(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    5151
_cell_measurement_theta_min      2.44
_cell_measurement_theta_max      26.69

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.288
_exptl_crystal_F_000             1716
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.33
_exptl_absorpt_coefficient_mu    0.517
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5909
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_process_details   'Sadabs 2014/4 (Bruker 2014)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'rotating-anode X-ray tube'
_diffrn_measurement_device_type  'Bruker X8-APEX II'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            20673
_diffrn_reflns_av_unetI/netI     0.0411
_diffrn_reflns_av_R_equivalents  0.0547
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         1.905
_diffrn_reflns_theta_max         26.855
_diffrn_reflns_theta_full        26.000
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4504
_reflns_number_gt                3821
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0650P)²+4.8199P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4504
_refine_ls_number_parameters     265
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0533
_refine_ls_R_factor_gt           0.0440
_refine_ls_wR_factor_ref         0.1214
_refine_ls_wR_factor_gt          0.1150
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.040
_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 0.500000 0.71294(3) 0.250000 0.01777(12) Uani 1 2 d S T P . .
C2_1 C 0.500000 0.5613(2) 0.250000 0.0228(6) Uani 1 2 d S T P . .
C3_1 C 0.45910(12) 0.50269(17) 0.27197(14) 0.0253(5) Uani 1 1 d . . . . .
C4_1 C 0.45807(14) 0.39768(18) 0.27185(16) 0.0333(5) Uani 1 1 d . . . . .
C5_1 C 0.500000 0.3426(2) 0.250000 0.0411(9) Uani 1 2 d S T P . .
H5_1 H 0.500001 0.270141 0.249999 0.049 Uiso 1 2 calc R U P . .
F1_2 F 0.41618(7) 0.54943(10) 0.29611(9) 0.0303(3) Uani 1 1 d . . . . .
F2_2 F 0.41509(10) 0.34679(11) 0.29338(12) 0.0495(4) Uani 1 1 d . . . . .
C1_3 C 0.54171(11) 0.74188(16) 0.37791(13) 0.0202(4) Uani 1 1 d . . . . .
N1_3 N 0.52145(10) 0.81214(14) 0.41742(11) 0.0233(4) Uani 1 1 d . . . . .
C2_3 C 0.56303(13) 0.80565(19) 0.51239(15) 0.0310(5) Uani 1 1 d . . . . .
H2_3 H 0.558485 0.846659 0.554052 0.037 Uiso 1 1 calc R U . . .
N2_3 N 0.59782(10) 0.69229(14) 0.45171(11) 0.0225(4) Uani 1 1 d . . . . .
C3_3 C 0.61041(13) 0.73073(19) 0.53340(15) 0.0309(5) Uani 1 1 d . . . . .
H3_3 H 0.646166 0.707837 0.593161 0.037 Uiso 1 1 calc R U . . .
C1_4 C 0.63882(11) 0.61015(17) 0.44661(13) 0.0230(4) Uani 1 1 d . . . . .
C2_4 C 0.68388(11) 0.63075(17) 0.41461(13) 0.0236(4) Uani 1 1 d . . . . .
C3_4 C 0.72406(12) 0.55044(18) 0.41281(15) 0.0268(5) Uani 1 1 d . . . . .
H3_4 H 0.755321 0.562662 0.391828 0.032 Uiso 1 1 calc R U . . .
C4_4 C 0.72018(13) 0.45226(18) 0.44075(16) 0.0300(5) Uani 1 1 d . . . . .
C5_4 C 0.67416(13) 0.43544(18) 0.47103(16) 0.0300(5) Uani 1 1 d . . . . .
H5_4 H 0.670826 0.368688 0.489740 0.036 Uiso 1 1 calc R U . . .
C6_4 C 0.63278(12) 0.51310(18) 0.47487(14) 0.0266(5) Uani 1 1 d . . . . .
C7_4 C 0.68719(12) 0.73454(17) 0.38080(16) 0.0283(5) Uani 1 1 d . . . . .
H7A_4 H 0.727188 0.736832 0.371209 0.042 Uiso 1 1 calc R U . . .
H7B_4 H 0.695059 0.786009 0.426197 0.042 Uiso 1 1 calc R U . . .
H7C_4 H 0.641490 0.748621 0.322911 0.042 Uiso 1 1 calc R U . . .
C8_4 C 0.76328(15) 0.3663(2) 0.4361(2) 0.0436(6) Uani 1 1 d . . . . .
H8A_4 H 0.731157 0.322082 0.384099 0.065 Uiso 1 1 calc R U . . .
H8B_4 H 0.785732 0.326498 0.492856 0.065 Uiso 1 1 calc R U . . .
H8C_4 H 0.801072 0.394080 0.428488 0.065 Uiso 1 1 calc R U . . .
C9_4 C 0.58222(14) 0.4917(2) 0.50582(17) 0.0350(5) Uani 1 1 d . . . . .
H9A_4 H 0.538639 0.533757 0.470604 0.052 Uiso 1 1 calc R U . . .
H9B_4 H 0.606334 0.507930 0.571001 0.052 Uiso 1 1 calc R U . . .
H9C_4 H 0.568665 0.419398 0.496060 0.052 Uiso 1 1 calc R U . . .
C1_5 C 0.46598(12) 0.88730(16) 0.36851(13) 0.0230(4) Uani 1 1 d . . . . .
C2_5 C 0.39496(12) 0.86421(16) 0.33955(14) 0.0245(4) Uani 1 1 d . . . . .
C3_5 C 0.34285(13) 0.93902(17) 0.29241(15) 0.0310(5) Uani 1 1 d . . . . .
H3_5 H 0.293773 0.924454 0.270938 0.037 Uiso 1 1 calc R U . . .
C4_5 C 0.36066(15) 1.03459(17) 0.27585(15) 0.0345(6) Uani 1 1 d . . . . .
C5_5 C 0.43196(15) 1.05518(17) 0.30723(16) 0.0350(6) Uani 1 1 d . . . . .
H5_5 H 0.444348 1.120750 0.296505 0.042 Uiso 1 1 calc R U . . .
C6_5 C 0.48636(14) 0.98287(17) 0.35415(15) 0.0303(5) Uani 1 1 d . . . . .
C7_5 C 0.56401(16) 1.0057(2) 0.38856(19) 0.0454(7) Uani 1 1 d . . . . .
H7A_5 H 0.580709 0.959293 0.359520 0.068 Uiso 1 1 calc R U . . .
H7B_5 H 0.593798 0.996310 0.455043 0.068 Uiso 1 1 calc R U . . .
H7C_5 H 0.568233 1.076346 0.373577 0.068 Uiso 1 1 calc R U . . .
C8_5 C 0.37623(14) 0.76239(17) 0.36089(18) 0.0323(5) Uani 1 1 d . . . . .
H8A_5 H 0.323529 0.756537 0.329771 0.049 Uiso 1 1 calc R U . . .
H8B_5 H 0.398640 0.756228 0.427091 0.049 Uiso 1 1 calc R U . . .
H8C_5 H 0.394282 0.707938 0.339736 0.049 Uiso 1 1 calc R U . . .
C9_5 C 0.30264(18) 1.1143(2) 0.22467(19) 0.0520(8) Uani 1 1 d . . . . .
H9A_5 H 0.286230 1.113089 0.159868 0.078 Uiso 1 1 calc R U . . .
H9B_5 H 0.322361 1.181880 0.250231 0.078 Uiso 1 1 calc R U . . .
H9C_5 H 0.261667 1.099776 0.230700 0.078 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 C1_3 1.930(2) 2_655 ?
Ni1 C1_3 1.930(2) . ?
Ni1 C2_1 1.988(3) . ?
C2_1 C3_1 1.384(3) . ?
C2_1 C3_1 1.384(3) 2_655 ?
C3_1 F1_2 1.368(3) . ?
C3_1 C4_1 1.377(3) . ?
C4_1 F2_2 1.364(3) . ?
C4_1 C5_1 1.376(3) . ?
C5_1 H5_1 0.9500 . ?
C1_3 N1_3 1.360(3) . ?
C1_3 N2_3 1.369(3) . ?
N1_3 C2_3 1.391(3) . ?
N1_3 C1_5 1.434(3) . ?
C2_3 C3_3 1.330(3) . ?
C2_3 H2_3 0.9500 . ?
N2_3 C3_3 1.387(3) . ?
N2_3 C1_4 1.437(3) . ?
C3_3 H3_3 0.9500 . ?
C1_4 C6_4 1.396(3) . ?
C1_4 C2_4 1.400(3) . ?
C2_4 C3_4 1.385(3) . ?
C2_4 C7_4 1.499(3) . ?
C3_4 C4_4 1.394(3) . ?
C3_4 H3_4 0.9500 . ?
C4_4 C5_4 1.388(3) . ?
C4_4 C8_4 1.502(3) . ?
C5_4 C6_4 1.390(3) . ?
C5_4 H5_4 0.9500 . ?
C6_4 C9_4 1.500(3) . ?
C7_4 H7A_4 0.9800 . ?
C7_4 H7B_4 0.9800 . ?
C7_4 H7C_4 0.9800 . ?
C8_4 H8A_4 0.9800 . ?
C8_4 H8B_4 0.9800 . ?
C8_4 H8C_4 0.9800 . ?
C9_4 H9A_4 0.9800 . ?
C9_4 H9B_4 0.9800 . ?
C9_4 H9C_4 0.9800 . ?
C1_5 C2_5 1.389(3) . ?
C1_5 C6_5 1.397(3) . ?
C2_5 C3_5 1.388(3) . ?
C2_5 C8_5 1.501(3) . ?
C3_5 C4_5 1.388(3) . ?
C3_5 H3_5 0.9500 . ?
C4_5 C5_5 1.378(4) . ?
C4_5 C9_5 1.510(3) . ?
C5_5 C6_5 1.391(4) . ?
C5_5 H5_5 0.9500 . ?
C6_5 C7_5 1.501(4) . ?
C7_5 H7A_5 0.9800 . ?
C7_5 H7B_5 0.9800 . ?
C7_5 H7C_5 0.9800 . ?
C8_5 H8A_5 0.9800 . ?
C8_5 H8B_5 0.9800 . ?
C8_5 H8C_5 0.9800 . ?
C9_5 H9A_5 0.9800 . ?
C9_5 H9B_5 0.9800 . ?
C9_5 H9C_5 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
C1_3 Ni1 C1_3 157.33(12) 2_655 . ?
C1_3 Ni1 C2_1 101.33(6) 2_655 . ?
C1_3 Ni1 C2_1 101.33(6) . . ?
C3_1 C2_1 C3_1 112.6(3) . 2_655 ?
C3_1 C2_1 Ni1 123.69(13) . . ?
C3_1 C2_1 Ni1 123.69(13) 2_655 . ?
F1_2 C3_1 C4_1 115.8(2) . . ?
F1_2 C3_1 C2_1 119.70(19) . . ?
C4_1 C3_1 C2_1 124.5(2) . . ?
F2_2 C4_1 C5_1 119.1(2) . . ?
F2_2 C4_1 C3_1 120.1(2) . . ?
C5_1 C4_1 C3_1 120.8(2) . . ?
C4_1 C5_1 C4_1 116.8(3) 2_655 . ?
C4_1 C5_1 H5_1 121.6 2_655 . ?
C4_1 C5_1 H5_1 121.6 . . ?
N1_3 C1_3 N2_3 102.87(17) . . ?
N1_3 C1_3 Ni1 129.39(15) . . ?
N2_3 C1_3 Ni1 127.68(15) . . ?
C1_3 N1_3 C2_3 111.99(18) . . ?
C1_3 N1_3 C1_5 124.83(17) . . ?
C2_3 N1_3 C1_5 123.13(17) . . ?
C3_3 C2_3 N1_3 106.49(19) . . ?
C3_3 C2_3 H2_3 126.8 . . ?
N1_3 C2_3 H2_3 126.8 . . ?
C1_3 N2_3 C3_3 111.49(18) . . ?
C1_3 N2_3 C1_4 125.02(17) . . ?
C3_3 N2_3 C1_4 123.49(18) . . ?
C2_3 C3_3 N2_3 107.15(19) . . ?
C2_3 C3_3 H3_3 126.4 . . ?
N2_3 C3_3 H3_3 126.4 . . ?
C6_4 C1_4 C2_4 122.6(2) . . ?
C6_4 C1_4 N2_3 118.58(19) . . ?
C2_4 C1_4 N2_3 118.83(19) . . ?
C3_4 C2_4 C1_4 117.3(2) . . ?
C3_4 C2_4 C7_4 120.9(2) . . ?
C1_4 C2_4 C7_4 121.7(2) . . ?
C2_4 C3_4 C4_4 122.2(2) . . ?
C2_4 C3_4 H3_4 118.9 . . ?
C4_4 C3_4 H3_4 118.9 . . ?
C5_4 C4_4 C3_4 118.3(2) . . ?
C5_4 C4_4 C8_4 120.7(2) . . ?
C3_4 C4_4 C8_4 121.0(2) . . ?
C4_4 C5_4 C6_4 122.1(2) . . ?
C4_4 C5_4 H5_4 118.9 . . ?
C6_4 C5_4 H5_4 118.9 . . ?
C5_4 C6_4 C1_4 117.4(2) . . ?
C5_4 C6_4 C9_4 120.7(2) . . ?
C1_4 C6_4 C9_4 121.8(2) . . ?
C2_4 C7_4 H7A_4 109.5 . . ?
C2_4 C7_4 H7B_4 109.5 . . ?
H7A_4 C7_4 H7B_4 109.5 . . ?
C2_4 C7_4 H7C_4 109.5 . . ?
H7A_4 C7_4 H7C_4 109.5 . . ?
H7B_4 C7_4 H7C_4 109.5 . . ?
C4_4 C8_4 H8A_4 109.5 . . ?
C4_4 C8_4 H8B_4 109.5 . . ?
H8A_4 C8_4 H8B_4 109.5 . . ?
C4_4 C8_4 H8C_4 109.5 . . ?
H8A_4 C8_4 H8C_4 109.5 . . ?
H8B_4 C8_4 H8C_4 109.5 . . ?
C6_4 C9_4 H9A_4 109.5 . . ?
C6_4 C9_4 H9B_4 109.5 . . ?
H9A_4 C9_4 H9B_4 109.5 . . ?
C6_4 C9_4 H9C_4 109.5 . . ?
H9A_4 C9_4 H9C_4 109.5 . . ?
H9B_4 C9_4 H9C_4 109.5 . . ?
C2_5 C1_5 C6_5 122.4(2) . . ?
C2_5 C1_5 N1_3 119.49(19) . . ?
C6_5 C1_5 N1_3 118.0(2) . . ?
C3_5 C2_5 C1_5 117.7(2) . . ?
C3_5 C2_5 C8_5 121.7(2) . . ?
C1_5 C2_5 C8_5 120.6(2) . . ?
C4_5 C3_5 C2_5 121.7(2) . . ?
C4_5 C3_5 H3_5 119.2 . . ?
C2_5 C3_5 H3_5 119.2 . . ?
C5_5 C4_5 C3_5 118.8(2) . . ?
C5_5 C4_5 C9_5 120.9(2) . . ?
C3_5 C4_5 C9_5 120.3(3) . . ?
C4_5 C5_5 C6_5 122.0(2) . . ?
C4_5 C5_5 H5_5 119.0 . . ?
C6_5 C5_5 H5_5 119.0 . . ?
C5_5 C6_5 C1_5 117.3(2) . . ?
C5_5 C6_5 C7_5 121.9(2) . . ?
C1_5 C6_5 C7_5 120.8(2) . . ?
C6_5 C7_5 H7A_5 109.5 . . ?
C6_5 C7_5 H7B_5 109.5 . . ?
H7A_5 C7_5 H7B_5 109.5 . . ?
C6_5 C7_5 H7C_5 109.5 . . ?
H7A_5 C7_5 H7C_5 109.5 . . ?
H7B_5 C7_5 H7C_5 109.5 . . ?
C2_5 C8_5 H8A_5 109.5 . . ?
C2_5 C8_5 H8B_5 109.5 . . ?
H8A_5 C8_5 H8B_5 109.5 . . ?
C2_5 C8_5 H8C_5 109.5 . . ?
H8A_5 C8_5 H8C_5 109.5 . . ?
H8B_5 C8_5 H8C_5 109.5 . . ?
C4_5 C9_5 H9A_5 109.5 . . ?
C4_5 C9_5 H9B_5 109.5 . . ?
H9A_5 C9_5 H9B_5 109.5 . . ?
C4_5 C9_5 H9C_5 109.5 . . ?
H9A_5 C9_5 H9C_5 109.5 . . ?
H9B_5 C9_5 H9C_5 109.5 . . ?

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
C3_1 C2_1 C3_1 F1_2 179.4(2) 2_655 . . . ?
Ni1 C2_1 C3_1 F1_2 -0.6(2) . . . . ?
C3_1 C2_1 C3_1 C4_1 -0.39(17) 2_655 . . . ?
Ni1 C2_1 C3_1 C4_1 179.61(17) . . . . ?
F1_2 C3_1 C4_1 F2_2 1.1(3) . . . . ?
C2_1 C3_1 C4_1 F2_2 -179.10(18) . . . . ?
F1_2 C3_1 C4_1 C5_1 -179.02(17) . . . . ?
C2_1 C3_1 C4_1 C5_1 0.8(3) . . . . ?
F2_2 C4_1 C5_1 C4_1 179.5(3) . . . 2_655 ?
C3_1 C4_1 C5_1 C4_1 -0.37(16) . . . 2_655 ?
N2_3 C1_3 N1_3 C2_3 -0.6(2) . . . . ?
Ni1 C1_3 N1_3 C2_3 176.74(17) . . . . ?
N2_3 C1_3 N1_3 C1_5 177.01(19) . . . . ?
Ni1 C1_3 N1_3 C1_5 -5.6(3) . . . . ?
C1_3 N1_3 C2_3 C3_3 0.3(3) . . . . ?
C1_5 N1_3 C2_3 C3_3 -177.4(2) . . . . ?
N1_3 C1_3 N2_3 C3_3 0.8(2) . . . . ?
Ni1 C1_3 N2_3 C3_3 -176.66(16) . . . . ?
N1_3 C1_3 N2_3 C1_4 -179.66(19) . . . . ?
Ni1 C1_3 N2_3 C1_4 2.9(3) . . . . ?
N1_3 C2_3 C3_3 N2_3 0.2(3) . . . . ?
C1_3 N2_3 C3_3 C2_3 -0.6(3) . . . . ?
C1_4 N2_3 C3_3 C2_3 179.8(2) . . . . ?
C1_3 N2_3 C1_4 C6_4 -112.8(2) . . . . ?
C3_3 N2_3 C1_4 C6_4 66.7(3) . . . . ?
C1_3 N2_3 C1_4 C2_4 67.9(3) . . . . ?
C3_3 N2_3 C1_4 C2_4 -112.5(2) . . . . ?
C6_4 C1_4 C2_4 C3_4 -0.8(3) . . . . ?
N2_3 C1_4 C2_4 C3_4 178.36(18) . . . . ?
C6_4 C1_4 C2_4 C7_4 177.3(2) . . . . ?
N2_3 C1_4 C2_4 C7_4 -3.5(3) . . . . ?
C1_4 C2_4 C3_4 C4_4 0.5(3) . . . . ?
C7_4 C2_4 C3_4 C4_4 -177.7(2) . . . . ?
C2_4 C3_4 C4_4 C5_4 0.2(3) . . . . ?
C2_4 C3_4 C4_4 C8_4 178.7(2) . . . . ?
C3_4 C4_4 C5_4 C6_4 -0.5(3) . . . . ?
C8_4 C4_4 C5_4 C6_4 -179.1(2) . . . . ?
C4_4 C5_4 C6_4 C1_4 0.2(3) . . . . ?
C4_4 C5_4 C6_4 C9_4 178.5(2) . . . . ?
C2_4 C1_4 C6_4 C5_4 0.5(3) . . . . ?
N2_3 C1_4 C6_4 C5_4 -178.70(19) . . . . ?
C2_4 C1_4 C6_4 C9_4 -177.8(2) . . . . ?
N2_3 C1_4 C6_4 C9_4 3.0(3) . . . . ?
C1_3 N1_3 C1_5 C2_5 89.9(3) . . . . ?
C2_3 N1_3 C1_5 C2_5 -92.7(3) . . . . ?
C1_3 N1_3 C1_5 C6_5 -91.9(2) . . . . ?
C2_3 N1_3 C1_5 C6_5 85.5(3) . . . . ?
C6_5 C1_5 C2_5 C3_5 1.9(3) . . . . ?
N1_3 C1_5 C2_5 C3_5 -179.99(18) . . . . ?
C6_5 C1_5 C2_5 C8_5 -176.7(2) . . . . ?
N1_3 C1_5 C2_5 C8_5 1.4(3) . . . . ?
C1_5 C2_5 C3_5 C4_5 -1.2(3) . . . . ?
C8_5 C2_5 C3_5 C4_5 177.4(2) . . . . ?
C2_5 C3_5 C4_5 C5_5 0.0(3) . . . . ?
C2_5 C3_5 C4_5 C9_5 -179.8(2) . . . . ?
C3_5 C4_5 C5_5 C6_5 0.6(3) . . . . ?
C9_5 C4_5 C5_5 C6_5 -179.7(2) . . . . ?
C4_5 C5_5 C6_5 C1_5 0.1(3) . . . . ?
C4_5 C5_5 C6_5 C7_5 -179.8(2) . . . . ?
C2_5 C1_5 C6_5 C5_5 -1.4(3) . . . . ?
N1_3 C1_5 C6_5 C5_5 -179.49(18) . . . . ?
C2_5 C1_5 C6_5 C7_5 178.5(2) . . . . ?
N1_3 C1_5 C6_5 C7_5 0.3(3) . . . . ?

_refine_diff_density_max         1.137
_refine_diff_density_min         -0.557
_refine_diff_density_rms         0.075

####################################################################### 
# 
# 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_Compound_8
_database_code_depnum_ccdc_archive 'CCDC 2017694'
loop_
_audit_author_name
_audit_author_address
'Udo Radius'
;University Wuerzburg
Germany
;
_audit_update_record             
;
2020-07-20 deposited with the CCDC.	2020-10-06 downloaded from the CCDC.
;


_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C42 H48 B F4 N4 Ni'
_chemical_formula_sum            'C42 H48 B F4 N4 Ni'
_chemical_formula_weight         754.36

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'
B B 0.0013 0.0007 '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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           52
_space_group_name_H-M_alt        'P n n a'
_space_group_name_Hall           '-P 2a 2bc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   15.9816(12)
_cell_length_b                   31.300(2)
_cell_length_c                   15.8502(12)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     7928.7(10)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9928
_cell_measurement_theta_min      2.23
_cell_measurement_theta_max      25.96

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.264
_exptl_crystal_F_000             3176
_exptl_crystal_size_max          0.512
_exptl_crystal_size_mid          0.486
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.542
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.6777
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_process_details   'Sadabs 2014/4 (Bruker 2014)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            91900
_diffrn_reflns_av_unetI/netI     0.0375
_diffrn_reflns_av_R_equivalents  0.0764
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -38
_diffrn_reflns_limit_k_max       38
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.301
_diffrn_reflns_theta_max         26.089
_diffrn_reflns_theta_full        26.000
_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 0.999
_reflns_number_total             7841
_reflns_number_gt                6046
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX3 v2016.5-0'
_computing_cell_refinement       'Bruker SAINT+ Integration Engine V8.37A'
_computing_data_reduction        'Bruker SAINT+ Integration Engine V8.37A'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0446P)²+12.6037P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7841
_refine_ls_number_parameters     483
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0759
_refine_ls_R_factor_gt           0.0528
_refine_ls_wR_factor_ref         0.1267
_refine_ls_wR_factor_gt          0.1166
_refine_ls_goodness_of_fit_ref   1.100
_refine_ls_restrained_S_all      1.100
_refine_ls_shift/su_max          0.021
_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 -0.22876(3) -0.2500 0.2500 0.01530(13) Uani 1 2 d S T P . .
N1_1 N -0.27140(15) -0.33385(7) 0.18085(15) 0.0206(5) Uani 1 1 d . . . . .
N2_1 N -0.20809(16) -0.34018(7) 0.29868(15) 0.0204(5) Uani 1 1 d . . . . .
C1_1 C -0.23446(17) -0.31031(9) 0.24253(17) 0.0190(6) Uani 1 1 d . . . . .
C2_1 C -0.2678(2) -0.37720(9) 0.1988(2) 0.0265(7) Uani 1 1 d . . . . .
H2_1 H -0.2895 -0.3997 0.1651 0.032 Uiso 1 1 calc R U . . .
C3_1 C -0.2279(2) -0.38138(9) 0.2728(2) 0.0264(7) Uani 1 1 d . . . . .
H3_1 H -0.2156 -0.4072 0.3016 0.032 Uiso 1 1 calc R U . . .
C4_1 C -0.16549(18) -0.33055(9) 0.37636(18) 0.0188(6) Uani 1 1 d . . . . .
C5_1 C -0.0787(2) -0.33521(10) 0.37974(19) 0.0256(7) Uani 1 1 d . . . . .
C6_1 C -0.03965(19) -0.32811(10) 0.4564(2) 0.0278(7) Uani 1 1 d . . . . .
H6_1 H 0.0192 -0.3319 0.4603 0.033 Uiso 1 1 calc R U . . .
C7_1 C -0.08370(19) -0.31558(9) 0.52754(19) 0.0230(7) Uani 1 1 d . . . . .
C8_1 C -0.16962(18) -0.30990(9) 0.52089(19) 0.0215(6) Uani 1 1 d . . . . .
H8_1 H -0.2000 -0.3003 0.5688 0.026 Uiso 1 1 calc R U . . .
C9_1 C -0.21236(18) -0.31779(9) 0.44637(19) 0.0199(6) Uani 1 1 d . . . . .
C10_1 C -0.0291(2) -0.34680(14) 0.3024(2) 0.0489(11) Uani 1 1 d . . . . .
H10A_1 H -0.0389 -0.3254 0.2583 0.073 Uiso 1 1 calc R U . . .
H10B_1 H -0.0468 -0.3750 0.2821 0.073 Uiso 1 1 calc R U . . .
H10C_1 H 0.0306 -0.3476 0.3165 0.073 Uiso 1 1 calc R U . . .
C11_1 C -0.0398(2) -0.30962(11) 0.6108(2) 0.0324(8) Uani 1 1 d . . . . .
H11A_1 H 0.0147 -0.2961 0.6013 0.049 Uiso 1 1 calc R U . . .
H11B_1 H -0.0316 -0.3375 0.6377 0.049 Uiso 1 1 calc R U . . .
H11C_1 H -0.0739 -0.2914 0.6475 0.049 Uiso 1 1 calc R U . . .
C12_1 C -0.30575(19) -0.31326(11) 0.4417(2) 0.0286(7) Uani 1 1 d . . . . .
H12A_1 H -0.3200 -0.2883 0.4073 0.043 Uiso 1 1 calc R U . . .
H12B_1 H -0.3284 -0.3096 0.4987 0.043 Uiso 1 1 calc R U . . .
H12C_1 H -0.3298 -0.3390 0.4160 0.043 Uiso 1 1 calc R U . . .
C13_1 C -0.31177(18) -0.31593(9) 0.10768(18) 0.0197(6) Uani 1 1 d . . . . .
C14_1 C -0.26453(18) -0.30882(9) 0.03501(18) 0.0213(6) Uani 1 1 d . . . . .
C15_1 C -0.30618(19) -0.29357(9) -0.0361(2) 0.0244(7) Uani 1 1 d . . . . .
H15_1 H -0.2753 -0.2881 -0.0861 0.029 Uiso 1 1 calc R U . . .
C16_1 C -0.3920(2) -0.28609(10) -0.0354(2) 0.0268(7) Uani 1 1 d . . . . .
C17_1 C -0.4356(2) -0.29286(10) 0.0381(2) 0.0288(7) Uani 1 1 d . . . . .
H17_1 H -0.4940 -0.2871 0.0391 0.035 Uiso 1 1 calc R U . . .
C18_1 C -0.3974(2) -0.30782(9) 0.1113(2) 0.0258(7) Uani 1 1 d . . . . .
C19_1 C -0.1721(2) -0.31679(12) 0.0330(2) 0.0337(8) Uani 1 1 d . . . . .
H19A_1 H -0.1438 -0.2963 0.0701 0.050 Uiso 1 1 calc R U . . .
H19B_1 H -0.1515 -0.3133 -0.0248 0.050 Uiso 1 1 calc R U . . .
H19C_1 H -0.1606 -0.3459 0.0524 0.050 Uiso 1 1 calc R U . . .
C20_1 C -0.4356(2) -0.27091(12) -0.1145(2) 0.0405(9) Uani 1 1 d . . . . .
H20A_1 H -0.3949 -0.2570 -0.1517 0.061 Uiso 1 1 calc R U . . .
H20B_1 H -0.4796 -0.2505 -0.0993 0.061 Uiso 1 1 calc R U . . .
H20C_1 H -0.4605 -0.2954 -0.1436 0.061 Uiso 1 1 calc R U . . .
C21_1 C -0.4458(2) -0.31378(12) 0.1918(2) 0.0379(9) Uani 1 1 d . . . . .
H21A_1 H -0.4398 -0.3434 0.2112 0.057 Uiso 1 1 calc R U . . .
H21B_1 H -0.5050 -0.3075 0.1817 0.057 Uiso 1 1 calc R U . . .
H21C_1 H -0.4240 -0.2943 0.2350 0.057 Uiso 1 1 calc R U . . .
Ni1_4 Ni -0.7500 -0.5000 0.23980(3) 0.01521(13) Uani 1 2 d S T P . .
N1_4 N -0.82503(14) -0.41572(7) 0.21044(15) 0.0187(5) Uani 1 1 d . . . . .
N2_4 N -0.70597(14) -0.41083(7) 0.27123(15) 0.0185(5) Uani 1 1 d . . . . .
C2_4 C -0.80898(19) -0.37248(9) 0.2220(2) 0.0256(7) Uani 1 1 d . . . . .
H2_4 H -0.8443 -0.3495 0.2059 0.031 Uiso 1 1 calc R U . . .
C3_4 C -0.73465(19) -0.36941(9) 0.2598(2) 0.0263(7) Uani 1 1 d . . . . .
H3_4 H -0.7068 -0.3439 0.2758 0.032 Uiso 1 1 calc R U . . .
C4_4 C -0.90075(17) -0.43265(9) 0.17434(18) 0.0183(6) Uani 1 1 d . . . . .
C5_4 C -0.91289(19) -0.42915(10) 0.08771(19) 0.0246(7) Uani 1 1 d . . . . .
C6_4 C -0.9886(2) -0.44336(11) 0.0551(2) 0.0310(8) Uani 1 1 d . . . . .
H6_4 H -0.9979 -0.4413 -0.0040 0.037 Uiso 1 1 calc R U . . .
C7_4 C -1.05059(19) -0.46042(11) 0.1052(2) 0.0273(7) Uani 1 1 d . . . . .
C8_4 C -1.03537(18) -0.46441(10) 0.19119(19) 0.0239(7) Uani 1 1 d . . . . .
H8_4 H -1.0770 -0.4769 0.2262 0.029 Uiso 1 1 calc R U . . .
C9_4 C -0.96106(18) -0.45073(9) 0.22722(18) 0.0202(6) Uani 1 1 d . . . . .
C10_4 C -0.8466(2) -0.41113(12) 0.0301(2) 0.0372(8) Uani 1 1 d . . . . .
H10A_4 H -0.7916 -0.4217 0.0477 0.056 Uiso 1 1 calc R U . . .
H10B_4 H -0.8474 -0.3799 0.0333 0.056 Uiso 1 1 calc R U . . .
H10C_4 H -0.8578 -0.4201 -0.0280 0.056 Uiso 1 1 calc R U . . .
C11_4 C -1.1337(2) -0.47348(13) 0.0685(2) 0.0424(9) Uani 1 1 d . . . . .
H11A_4 H -1.1256 -0.4834 0.0104 0.064 Uiso 1 1 calc R U . . .
H11B_4 H -1.1718 -0.4489 0.0688 0.064 Uiso 1 1 calc R U . . .
H11C_4 H -1.1577 -0.4966 0.1024 0.064 Uiso 1 1 calc R U . . .
C12_4 C -0.9471(2) -0.45507(11) 0.32071(19) 0.0282(7) Uani 1 1 d . . . . .
H12A_4 H -0.9101 -0.4794 0.3316 0.042 Uiso 1 1 calc R U . . .
H12B_4 H -1.0009 -0.4598 0.3489 0.042 Uiso 1 1 calc R U . . .
H12C_4 H -0.9213 -0.4289 0.3425 0.042 Uiso 1 1 calc R U . . .
C13_4 C -0.62939(17) -0.42153(9) 0.31450(18) 0.0178(6) Uani 1 1 d . . . . .
C14_4 C -0.55553(18) -0.42434(10) 0.26839(18) 0.0221(6) Uani 1 1 d . . . . .
C15_4 C -0.48189(18) -0.43204(10) 0.31247(19) 0.0244(7) Uani 1 1 d . . . . .
H15_4 H -0.4307 -0.4342 0.2822 0.029 Uiso 1 1 calc R U . . .
C16_4 C -0.48124(19) -0.43663(10) 0.3996(2) 0.0243(7) Uani 1 1 d . . . . .
C17_4 C -0.55703(19) -0.43441(9) 0.44251(19) 0.0239(7) Uani 1 1 d . . . . .
H17_4 H -0.5572 -0.4381 0.5020 0.029 Uiso 1 1 calc R U . . .
C18_4 C -0.63196(18) -0.42707(9) 0.40167(19) 0.0217(6) Uani 1 1 d . . . . .
C19_4 C -0.5553(2) -0.42038(12) 0.1738(2) 0.0339(8) Uani 1 1 d . . . . .
H19A_4 H -0.5838 -0.3939 0.1574 0.051 Uiso 1 1 calc R U . . .
H19B_4 H -0.5846 -0.4449 0.1490 0.051 Uiso 1 1 calc R U . . .
H19C_4 H -0.4975 -0.4197 0.1533 0.051 Uiso 1 1 calc R U . . .
C20_4 C -0.4006(2) -0.44365(12) 0.4464(2) 0.0346(8) Uani 1 1 d . . . . .
H20A_4 H -0.3538 -0.4433 0.4065 0.052 Uiso 1 1 calc R U . . .
H20B_4 H -0.4025 -0.4714 0.4751 0.052 Uiso 1 1 calc R U . . .
H20C_4 H -0.3931 -0.4209 0.4882 0.052 Uiso 1 1 calc R U . . .
C21_4 C -0.7133(2) -0.42531(11) 0.4495(2) 0.0299(7) Uani 1 1 d . . . . .
H21A_4 H -0.7025 -0.4298 0.5097 0.045 Uiso 1 1 calc R U . . .
H21B_4 H -0.7509 -0.4477 0.4288 0.045 Uiso 1 1 calc R U . . .
H21C_4 H -0.7395 -0.3973 0.4412 0.045 Uiso 1 1 calc R U . . .
C1_4 C -0.76126(16) -0.43983(9) 0.24103(17) 0.0177(6) Uani 1 1 d . . . . .
F1_3 F -0.66413(14) -0.27522(6) 0.19810(13) 0.0412(5) Uani 1 1 d . . . . .
F2_3 F -0.76446(14) -0.27622(6) 0.29922(12) 0.0386(5) Uani 1 1 d . . . . .
B1_3 B -0.7132(4) -0.2500 0.2500 0.0319(12) Uani 1 2 d S T P . .
F1_4 F -0.30479(11) -0.52349(5) 0.34208(12) 0.0308(4) Uani 1 1 d . . . . .
F2_4 F -0.29534(10) -0.47195(5) 0.24089(12) 0.0281(4) Uani 1 1 d . . . . .
B1_4 B -0.2500 -0.5000 0.2921(3) 0.0224(10) Uani 1 2 d S T P . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ni1 C1_1 1.894(3) 3_545 ?
Ni1 C1_1 1.894(3) . ?
N1_1 C1_1 1.359(4) . ?
N1_1 C2_1 1.388(4) . ?
N1_1 C13_1 1.441(4) . ?
N2_1 C1_1 1.358(4) . ?
N2_1 C3_1 1.390(4) . ?
N2_1 C4_1 1.439(4) . ?
C2_1 C3_1 1.341(4) . ?
C2_1 H2_1 0.9500 . ?
C3_1 H3_1 0.9500 . ?
C4_1 C5_1 1.396(4) . ?
C4_1 C9_1 1.397(4) . ?
C5_1 C6_1 1.383(5) . ?
C5_1 C10_1 1.504(4) . ?
C6_1 C7_1 1.387(4) . ?
C6_1 H6_1 0.9500 . ?
C7_1 C8_1 1.389(4) . ?
C7_1 C11_1 1.506(4) . ?
C8_1 C9_1 1.387(4) . ?
C8_1 H8_1 0.9500 . ?
C9_1 C12_1 1.501(4) . ?
C10_1 H10A_1 0.9800 . ?
C10_1 H10B_1 0.9800 . ?
C10_1 H10C_1 0.9800 . ?
C11_1 H11A_1 0.9800 . ?
C11_1 H11B_1 0.9800 . ?
C11_1 H11C_1 0.9800 . ?
C12_1 H12A_1 0.9800 . ?
C12_1 H12B_1 0.9800 . ?
C12_1 H12C_1 0.9800 . ?
C13_1 C18_1 1.393(4) . ?
C13_1 C14_1 1.395(4) . ?
C14_1 C15_1 1.393(4) . ?
C14_1 C19_1 1.498(4) . ?
C15_1 C16_1 1.391(4) . ?
C15_1 H15_1 0.9500 . ?
C16_1 C17_1 1.375(5) . ?
C16_1 C20_1 1.510(4) . ?
C17_1 C18_1 1.391(5) . ?
C17_1 H17_1 0.9500 . ?
C18_1 C21_1 1.504(4) . ?
C19_1 H19A_1 0.9800 . ?
C19_1 H19B_1 0.9800 . ?
C19_1 H19C_1 0.9800 . ?
C20_1 H20A_1 0.9800 . ?
C20_1 H20B_1 0.9800 . ?
C20_1 H20C_1 0.9800 . ?
C21_1 H21A_1 0.9800 . ?
C21_1 H21B_1 0.9800 . ?
C21_1 H21C_1 0.9800 . ?
Ni1_4 C1_4 1.892(3) 2_345 ?
Ni1_4 C1_4 1.892(3) . ?
N1_4 C1_4 1.358(4) . ?
N1_4 C2_4 1.389(4) . ?
N1_4 C4_4 1.440(4) . ?
N2_4 C1_4 1.354(4) . ?
N2_4 C3_4 1.387(4) . ?
N2_4 C13_4 1.442(4) . ?
C2_4 C3_4 1.334(4) . ?
C2_4 H2_4 0.9500 . ?
C3_4 H3_4 0.9500 . ?
C4_4 C5_4 1.391(4) . ?
C4_4 C9_4 1.397(4) . ?
C5_4 C6_4 1.389(4) . ?
C5_4 C10_4 1.507(4) . ?
C6_4 C7_4 1.379(4) . ?
C6_4 H6_4 0.9500 . ?
C7_4 C8_4 1.389(4) . ?
C7_4 C11_4 1.506(4) . ?
C8_4 C9_4 1.386(4) . ?
C8_4 H8_4 0.9500 . ?
C9_4 C12_4 1.504(4) . ?
C10_4 H10A_4 0.9800 . ?
C10_4 H10B_4 0.9800 . ?
C10_4 H10C_4 0.9800 . ?
C11_4 H11A_4 0.9800 . ?
C11_4 H11B_4 0.9800 . ?
C11_4 H11C_4 0.9800 . ?
C12_4 H12A_4 0.9800 . ?
C12_4 H12B_4 0.9800 . ?
C12_4 H12C_4 0.9800 . ?
C13_4 C14_4 1.391(4) . ?
C13_4 C18_4 1.393(4) . ?
C14_4 C15_4 1.390(4) . ?
C14_4 C19_4 1.504(4) . ?
C15_4 C16_4 1.388(4) . ?
C15_4 H15_4 0.9500 . ?
C16_4 C17_4 1.391(4) . ?
C16_4 C20_4 1.503(4) . ?
C17_4 C18_4 1.381(4) . ?
C17_4 H17_4 0.9500 . ?
C18_4 C21_4 1.506(4) . ?
C19_4 H19A_4 0.9800 . ?
C19_4 H19B_4 0.9800 . ?
C19_4 H19C_4 0.9800 . ?
C20_4 H20A_4 0.9800 . ?
C20_4 H20B_4 0.9800 . ?
C20_4 H20C_4 0.9800 . ?
C21_4 H21A_4 0.9800 . ?
C21_4 H21B_4 0.9800 . ?
C21_4 H21C_4 0.9800 . ?
F1_3 B1_3 1.384(4) . ?
F2_3 B1_3 1.397(4) . ?
B1_3 F1_3 1.384(4) 3_545 ?
B1_3 F2_3 1.397(4) 3_545 ?
F1_4 B1_4 1.391(3) . ?
F2_4 B1_4 1.399(3) . ?
B1_4 F1_4 1.391(3) 2_445 ?
B1_4 F2_4 1.399(3) 2_445 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1_1 Ni1 C1_1 174.48(17) 3_545 . ?
C1_1 N1_1 C2_1 111.4(2) . . ?
C1_1 N1_1 C13_1 124.2(2) . . ?
C2_1 N1_1 C13_1 124.4(2) . . ?
C1_1 N2_1 C3_1 112.0(2) . . ?
C1_1 N2_1 C4_1 124.3(2) . . ?
C3_1 N2_1 C4_1 123.7(2) . . ?
N2_1 C1_1 N1_1 103.5(2) . . ?
N2_1 C1_1 Ni1 129.1(2) . . ?
N1_1 C1_1 Ni1 127.3(2) . . ?
C3_1 C2_1 N1_1 107.1(3) . . ?
C3_1 C2_1 H2_1 126.4 . . ?
N1_1 C2_1 H2_1 126.4 . . ?
C2_1 C3_1 N2_1 106.0(3) . . ?
C2_1 C3_1 H3_1 127.0 . . ?
N2_1 C3_1 H3_1 127.0 . . ?
C5_1 C4_1 C9_1 122.2(3) . . ?
C5_1 C4_1 N2_1 118.8(3) . . ?
C9_1 C4_1 N2_1 119.1(3) . . ?
C6_1 C5_1 C4_1 117.7(3) . . ?
C6_1 C5_1 C10_1 121.1(3) . . ?
C4_1 C5_1 C10_1 121.2(3) . . ?
C5_1 C6_1 C7_1 122.1(3) . . ?
C5_1 C6_1 H6_1 119.0 . . ?
C7_1 C6_1 H6_1 119.0 . . ?
C6_1 C7_1 C8_1 118.5(3) . . ?
C6_1 C7_1 C11_1 120.8(3) . . ?
C8_1 C7_1 C11_1 120.8(3) . . ?
C9_1 C8_1 C7_1 121.9(3) . . ?
C9_1 C8_1 H8_1 119.0 . . ?
C7_1 C8_1 H8_1 119.0 . . ?
C8_1 C9_1 C4_1 117.6(3) . . ?
C8_1 C9_1 C12_1 121.0(3) . . ?
C4_1 C9_1 C12_1 121.4(3) . . ?
C5_1 C10_1 H10A_1 109.5 . . ?
C5_1 C10_1 H10B_1 109.5 . . ?
H10A_1 C10_1 H10B_1 109.5 . . ?
C5_1 C10_1 H10C_1 109.5 . . ?
H10A_1 C10_1 H10C_1 109.5 . . ?
H10B_1 C10_1 H10C_1 109.5 . . ?
C7_1 C11_1 H11A_1 109.5 . . ?
C7_1 C11_1 H11B_1 109.5 . . ?
H11A_1 C11_1 H11B_1 109.5 . . ?
C7_1 C11_1 H11C_1 109.5 . . ?
H11A_1 C11_1 H11C_1 109.5 . . ?
H11B_1 C11_1 H11C_1 109.5 . . ?
C9_1 C12_1 H12A_1 109.5 . . ?
C9_1 C12_1 H12B_1 109.5 . . ?
H12A_1 C12_1 H12B_1 109.5 . . ?
C9_1 C12_1 H12C_1 109.5 . . ?
H12A_1 C12_1 H12C_1 109.5 . . ?
H12B_1 C12_1 H12C_1 109.5 . . ?
C18_1 C13_1 C14_1 122.4(3) . . ?
C18_1 C13_1 N1_1 118.6(3) . . ?
C14_1 C13_1 N1_1 119.0(3) . . ?
C15_1 C14_1 C13_1 117.6(3) . . ?
C15_1 C14_1 C19_1 120.7(3) . . ?
C13_1 C14_1 C19_1 121.7(3) . . ?
C16_1 C15_1 C14_1 121.5(3) . . ?
C16_1 C15_1 H15_1 119.2 . . ?
C14_1 C15_1 H15_1 119.2 . . ?
C17_1 C16_1 C15_1 118.7(3) . . ?
C17_1 C16_1 C20_1 121.2(3) . . ?
C15_1 C16_1 C20_1 120.1(3) . . ?
C16_1 C17_1 C18_1 122.4(3) . . ?
C16_1 C17_1 H17_1 118.8 . . ?
C18_1 C17_1 H17_1 118.8 . . ?
C17_1 C18_1 C13_1 117.3(3) . . ?
C17_1 C18_1 C21_1 121.5(3) . . ?
C13_1 C18_1 C21_1 121.1(3) . . ?
C14_1 C19_1 H19A_1 109.5 . . ?
C14_1 C19_1 H19B_1 109.5 . . ?
H19A_1 C19_1 H19B_1 109.5 . . ?
C14_1 C19_1 H19C_1 109.5 . . ?
H19A_1 C19_1 H19C_1 109.5 . . ?
H19B_1 C19_1 H19C_1 109.5 . . ?
C16_1 C20_1 H20A_1 109.5 . . ?
C16_1 C20_1 H20B_1 109.5 . . ?
H20A_1 C20_1 H20B_1 109.5 . . ?
C16_1 C20_1 H20C_1 109.5 . . ?
H20A_1 C20_1 H20C_1 109.5 . . ?
H20B_1 C20_1 H20C_1 109.5 . . ?
C18_1 C21_1 H21A_1 109.5 . . ?
C18_1 C21_1 H21B_1 109.5 . . ?
H21A_1 C21_1 H21B_1 109.5 . . ?
C18_1 C21_1 H21C_1 109.5 . . ?
H21A_1 C21_1 H21C_1 109.5 . . ?
H21B_1 C21_1 H21C_1 109.5 . . ?
C1_4 Ni1_4 C1_4 178.82(17) 2_345 . ?
C1_4 N1_4 C2_4 110.9(2) . . ?
C1_4 N1_4 C4_4 124.6(2) . . ?
C2_4 N1_4 C4_4 124.5(2) . . ?
C1_4 N2_4 C3_4 111.4(2) . . ?
C1_4 N2_4 C13_4 124.5(2) . . ?
C3_4 N2_4 C13_4 124.0(2) . . ?
C3_4 C2_4 N1_4 107.1(3) . . ?
C3_4 C2_4 H2_4 126.5 . . ?
N1_4 C2_4 H2_4 126.5 . . ?
C2_4 C3_4 N2_4 106.6(3) . . ?
C2_4 C3_4 H3_4 126.7 . . ?
N2_4 C3_4 H3_4 126.7 . . ?
C5_4 C4_4 C9_4 121.9(3) . . ?
C5_4 C4_4 N1_4 118.7(3) . . ?
C9_4 C4_4 N1_4 119.4(3) . . ?
C6_4 C5_4 C4_4 117.7(3) . . ?
C6_4 C5_4 C10_4 120.4(3) . . ?
C4_4 C5_4 C10_4 121.9(3) . . ?
C7_4 C6_4 C5_4 122.4(3) . . ?
C7_4 C6_4 H6_4 118.8 . . ?
C5_4 C6_4 H6_4 118.8 . . ?
C6_4 C7_4 C8_4 118.3(3) . . ?
C6_4 C7_4 C11_4 121.0(3) . . ?
C8_4 C7_4 C11_4 120.6(3) . . ?
C9_4 C8_4 C7_4 121.8(3) . . ?
C9_4 C8_4 H8_4 119.1 . . ?
C7_4 C8_4 H8_4 119.1 . . ?
C8_4 C9_4 C4_4 118.0(3) . . ?
C8_4 C9_4 C12_4 120.3(3) . . ?
C4_4 C9_4 C12_4 121.7(3) . . ?
C5_4 C10_4 H10A_4 109.5 . . ?
C5_4 C10_4 H10B_4 109.5 . . ?
H10A_4 C10_4 H10B_4 109.5 . . ?
C5_4 C10_4 H10C_4 109.5 . . ?
H10A_4 C10_4 H10C_4 109.5 . . ?
H10B_4 C10_4 H10C_4 109.5 . . ?
C7_4 C11_4 H11A_4 109.5 . . ?
C7_4 C11_4 H11B_4 109.5 . . ?
H11A_4 C11_4 H11B_4 109.5 . . ?
C7_4 C11_4 H11C_4 109.5 . . ?
H11A_4 C11_4 H11C_4 109.5 . . ?
H11B_4 C11_4 H11C_4 109.5 . . ?
C9_4 C12_4 H12A_4 109.5 . . ?
C9_4 C12_4 H12B_4 109.5 . . ?
H12A_4 C12_4 H12B_4 109.5 . . ?
C9_4 C12_4 H12C_4 109.5 . . ?
H12A_4 C12_4 H12C_4 109.5 . . ?
H12B_4 C12_4 H12C_4 109.5 . . ?
C14_4 C13_4 C18_4 122.6(3) . . ?
C14_4 C13_4 N2_4 119.0(3) . . ?
C18_4 C13_4 N2_4 118.4(2) . . ?
C15_4 C14_4 C13_4 117.7(3) . . ?
C15_4 C14_4 C19_4 120.9(3) . . ?
C13_4 C14_4 C19_4 121.3(3) . . ?
C16_4 C15_4 C14_4 121.6(3) . . ?
C16_4 C15_4 H15_4 119.2 . . ?
C14_4 C15_4 H15_4 119.2 . . ?
C15_4 C16_4 C17_4 118.4(3) . . ?
C15_4 C16_4 C20_4 120.9(3) . . ?
C17_4 C16_4 C20_4 120.8(3) . . ?
C18_4 C17_4 C16_4 122.3(3) . . ?
C18_4 C17_4 H17_4 118.9 . . ?
C16_4 C17_4 H17_4 118.9 . . ?
C17_4 C18_4 C13_4 117.4(3) . . ?
C17_4 C18_4 C21_4 121.3(3) . . ?
C13_4 C18_4 C21_4 121.3(3) . . ?
C14_4 C19_4 H19A_4 109.5 . . ?
C14_4 C19_4 H19B_4 109.5 . . ?
H19A_4 C19_4 H19B_4 109.5 . . ?
C14_4 C19_4 H19C_4 109.5 . . ?
H19A_4 C19_4 H19C_4 109.5 . . ?
H19B_4 C19_4 H19C_4 109.5 . . ?
C16_4 C20_4 H20A_4 109.5 . . ?
C16_4 C20_4 H20B_4 109.5 . . ?
H20A_4 C20_4 H20B_4 109.5 . . ?
C16_4 C20_4 H20C_4 109.5 . . ?
H20A_4 C20_4 H20C_4 109.5 . . ?
H20B_4 C20_4 H20C_4 109.5 . . ?
C18_4 C21_4 H21A_4 109.5 . . ?
C18_4 C21_4 H21B_4 109.5 . . ?
H21A_4 C21_4 H21B_4 109.5 . . ?
C18_4 C21_4 H21C_4 109.5 . . ?
H21A_4 C21_4 H21C_4 109.5 . . ?
H21B_4 C21_4 H21C_4 109.5 . . ?
N2_4 C1_4 N1_4 104.1(2) . . ?
N2_4 C1_4 Ni1_4 127.5(2) . . ?
N1_4 C1_4 Ni1_4 128.4(2) . . ?
F1_3 B1_3 F1_3 110.9(5) . 3_545 ?
F1_3 B1_3 F2_3 109.60(12) . 3_545 ?
F1_3 B1_3 F2_3 109.21(11) 3_545 3_545 ?
F1_3 B1_3 F2_3 109.21(11) . . ?
F1_3 B1_3 F2_3 109.60(12) 3_545 . ?
F2_3 B1_3 F2_3 108.2(5) 3_545 . ?
F1_4 B1_4 F1_4 110.6(4) 2_445 . ?
F1_4 B1_4 F2_4 109.66(11) 2_445 2_445 ?
F1_4 B1_4 F2_4 108.96(10) . 2_445 ?
F1_4 B1_4 F2_4 108.96(10) 2_445 . ?
F1_4 B1_4 F2_4 109.66(11) . . ?
F2_4 B1_4 F2_4 109.0(4) 2_445 . ?

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
C3_1 N2_1 C1_1 N1_1 0.1(3) . . . . ?
C4_1 N2_1 C1_1 N1_1 -179.3(3) . . . . ?
C3_1 N2_1 C1_1 Ni1 176.3(2) . . . . ?
C4_1 N2_1 C1_1 Ni1 -3.0(4) . . . . ?
C2_1 N1_1 C1_1 N2_1 0.0(3) . . . . ?
C13_1 N1_1 C1_1 N2_1 178.0(2) . . . . ?
C2_1 N1_1 C1_1 Ni1 -176.3(2) . . . . ?
C13_1 N1_1 C1_1 Ni1 1.6(4) . . . . ?
C1_1 N1_1 C2_1 C3_1 -0.2(4) . . . . ?
C13_1 N1_1 C2_1 C3_1 -178.1(3) . . . . ?
N1_1 C2_1 C3_1 N2_1 0.2(4) . . . . ?
C1_1 N2_1 C3_1 C2_1 -0.2(4) . . . . ?
C4_1 N2_1 C3_1 C2_1 179.2(3) . . . . ?
C1_1 N2_1 C4_1 C5_1 -100.7(3) . . . . ?
C3_1 N2_1 C4_1 C5_1 80.0(4) . . . . ?
C1_1 N2_1 C4_1 C9_1 80.7(4) . . . . ?
C3_1 N2_1 C4_1 C9_1 -98.6(3) . . . . ?
C9_1 C4_1 C5_1 C6_1 2.1(4) . . . . ?
N2_1 C4_1 C5_1 C6_1 -176.4(3) . . . . ?
C9_1 C4_1 C5_1 C10_1 -176.8(3) . . . . ?
N2_1 C4_1 C5_1 C10_1 4.6(5) . . . . ?
C4_1 C5_1 C6_1 C7_1 -1.8(5) . . . . ?
C10_1 C5_1 C6_1 C7_1 177.1(3) . . . . ?
C5_1 C6_1 C7_1 C8_1 -0.3(5) . . . . ?
C5_1 C6_1 C7_1 C11_1 177.8(3) . . . . ?
C6_1 C7_1 C8_1 C9_1 2.2(4) . . . . ?
C11_1 C7_1 C8_1 C9_1 -175.9(3) . . . . ?
C7_1 C8_1 C9_1 C4_1 -2.0(4) . . . . ?
C7_1 C8_1 C9_1 C12_1 177.3(3) . . . . ?
C5_1 C4_1 C9_1 C8_1 -0.3(4) . . . . ?
N2_1 C4_1 C9_1 C8_1 178.3(2) . . . . ?
C5_1 C4_1 C9_1 C12_1 -179.6(3) . . . . ?
N2_1 C4_1 C9_1 C12_1 -1.0(4) . . . . ?
C1_1 N1_1 C13_1 C18_1 -92.3(3) . . . . ?
C2_1 N1_1 C13_1 C18_1 85.3(4) . . . . ?
C1_1 N1_1 C13_1 C14_1 90.0(3) . . . . ?
C2_1 N1_1 C13_1 C14_1 -92.3(4) . . . . ?
C18_1 C13_1 C14_1 C15_1 -0.8(4) . . . . ?
N1_1 C13_1 C14_1 C15_1 176.7(2) . . . . ?
C18_1 C13_1 C14_1 C19_1 178.6(3) . . . . ?
N1_1 C13_1 C14_1 C19_1 -3.9(4) . . . . ?
C13_1 C14_1 C15_1 C16_1 -0.8(4) . . . . ?
C19_1 C14_1 C15_1 C16_1 179.8(3) . . . . ?
C14_1 C15_1 C16_1 C17_1 1.9(5) . . . . ?
C14_1 C15_1 C16_1 C20_1 -178.0(3) . . . . ?
C15_1 C16_1 C17_1 C18_1 -1.5(5) . . . . ?
C20_1 C16_1 C17_1 C18_1 178.4(3) . . . . ?
C16_1 C17_1 C18_1 C13_1 0.0(5) . . . . ?
C16_1 C17_1 C18_1 C21_1 178.2(3) . . . . ?
C14_1 C13_1 C18_1 C17_1 1.2(4) . . . . ?
N1_1 C13_1 C18_1 C17_1 -176.3(3) . . . . ?
C14_1 C13_1 C18_1 C21_1 -177.0(3) . . . . ?
N1_1 C13_1 C18_1 C21_1 5.4(4) . . . . ?
C1_4 N1_4 C2_4 C3_4 0.1(4) . . . . ?
C4_4 N1_4 C2_4 C3_4 177.6(3) . . . . ?
N1_4 C2_4 C3_4 N2_4 -0.1(3) . . . . ?
C1_4 N2_4 C3_4 C2_4 0.0(4) . . . . ?
C13_4 N2_4 C3_4 C2_4 -176.4(3) . . . . ?
C1_4 N1_4 C4_4 C5_4 -108.4(3) . . . . ?
C2_4 N1_4 C4_4 C5_4 74.5(4) . . . . ?
C1_4 N1_4 C4_4 C9_4 73.8(4) . . . . ?
C2_4 N1_4 C4_4 C9_4 -103.3(3) . . . . ?
C9_4 C4_4 C5_4 C6_4 1.6(5) . . . . ?
N1_4 C4_4 C5_4 C6_4 -176.2(3) . . . . ?
C9_4 C4_4 C5_4 C10_4 -177.7(3) . . . . ?
N1_4 C4_4 C5_4 C10_4 4.5(4) . . . . ?
C4_4 C5_4 C6_4 C7_4 0.1(5) . . . . ?
C10_4 C5_4 C6_4 C7_4 179.4(3) . . . . ?
C5_4 C6_4 C7_4 C8_4 -1.7(5) . . . . ?
C5_4 C6_4 C7_4 C11_4 176.8(3) . . . . ?
C6_4 C7_4 C8_4 C9_4 1.8(5) . . . . ?
C11_4 C7_4 C8_4 C9_4 -176.8(3) . . . . ?
C7_4 C8_4 C9_4 C4_4 -0.2(5) . . . . ?
C7_4 C8_4 C9_4 C12_4 179.2(3) . . . . ?
C5_4 C4_4 C9_4 C8_4 -1.5(4) . . . . ?
N1_4 C4_4 C9_4 C8_4 176.2(3) . . . . ?
C5_4 C4_4 C9_4 C12_4 179.1(3) . . . . ?
N1_4 C4_4 C9_4 C12_4 -3.2(4) . . . . ?
C1_4 N2_4 C13_4 C14_4 94.1(3) . . . . ?
C3_4 N2_4 C13_4 C14_4 -90.0(3) . . . . ?
C1_4 N2_4 C13_4 C18_4 -88.3(3) . . . . ?
C3_4 N2_4 C13_4 C18_4 87.6(3) . . . . ?
C18_4 C13_4 C14_4 C15_4 -1.5(4) . . . . ?
N2_4 C13_4 C14_4 C15_4 176.0(3) . . . . ?
C18_4 C13_4 C14_4 C19_4 176.9(3) . . . . ?
N2_4 C13_4 C14_4 C19_4 -5.6(4) . . . . ?
C13_4 C14_4 C15_4 C16_4 -0.3(5) . . . . ?
C19_4 C14_4 C15_4 C16_4 -178.7(3) . . . . ?
C14_4 C15_4 C16_4 C17_4 1.6(5) . . . . ?
C14_4 C15_4 C16_4 C20_4 -178.2(3) . . . . ?
C15_4 C16_4 C17_4 C18_4 -1.2(5) . . . . ?
C20_4 C16_4 C17_4 C18_4 178.6(3) . . . . ?
C16_4 C17_4 C18_4 C13_4 -0.4(4) . . . . ?
C16_4 C17_4 C18_4 C21_4 179.3(3) . . . . ?
C14_4 C13_4 C18_4 C17_4 1.8(4) . . . . ?
N2_4 C13_4 C18_4 C17_4 -175.7(2) . . . . ?
C14_4 C13_4 C18_4 C21_4 -177.9(3) . . . . ?
N2_4 C13_4 C18_4 C21_4 4.6(4) . . . . ?
C3_4 N2_4 C1_4 N1_4 0.1(3) . . . . ?
C13_4 N2_4 C1_4 N1_4 176.5(2) . . . . ?
C3_4 N2_4 C1_4 Ni1_4 178.7(2) . . . . ?
C13_4 N2_4 C1_4 Ni1_4 -4.9(4) . . . . ?
C2_4 N1_4 C1_4 N2_4 -0.1(3) . . . . ?
C4_4 N1_4 C1_4 N2_4 -177.5(2) . . . . ?
C2_4 N1_4 C1_4 Ni1_4 -178.7(2) . . . . ?
C4_4 N1_4 C1_4 Ni1_4 3.8(4) . . . . ?

_refine_diff_density_max         2.019
_refine_diff_density_min         -0.630
_refine_diff_density_rms         0.069

####################################################################### 
# 
# 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_Compound_3
_database_code_depnum_ccdc_archive 'CCDC 2017698'
loop_
_audit_author_name
_audit_author_address
'Udo Radius'
;University Wuerzburg
Germany
;
_audit_update_record             
;
2020-07-20 deposited with the CCDC.	2020-10-06 downloaded from the CCDC.
;


_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C48 H48 F6 N4 Ni'
_chemical_formula_sum            'C48 H48 F6 N4 Ni'
_chemical_formula_weight         853.61

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-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                   20.5349(10)
_cell_length_b                   18.6375(9)
_cell_length_c                   22.7188(12)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     8694.9(8)
_cell_formula_units_Z            8
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    9480
_cell_measurement_theta_min      2.19
_cell_measurement_theta_max      26.61

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.304
_exptl_crystal_F_000             3568
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.337
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.305
_exptl_absorpt_coefficient_mu    0.510
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6873
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_process_details   
'SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'rotating anode'

_diffrn_measurement_device_type  'Bruker X8-APEX II'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            115783
_diffrn_reflns_av_unetI/netI     0.0297
_diffrn_reflns_av_R_equivalents  0.0600
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         1.726
_diffrn_reflns_theta_max         26.806
_diffrn_reflns_theta_full        26.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             9293
_reflns_number_gt                6964
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0501P)²+9.6430P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         9293
_refine_ls_number_parameters     620
_refine_ls_number_restraints     372
_refine_ls_R_factor_all          0.0815
_refine_ls_R_factor_gt           0.0567
_refine_ls_wR_factor_ref         0.1358
_refine_ls_wR_factor_gt          0.1233
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_restrained_S_all      1.144
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Ni1 Ni 0.61645(2) 0.40651(2) 0.27686(2) 0.02711(10) Uani 1 1 d . . . . .
C1A_1 C 0.5403(3) 0.4607(5) 0.2890(4) 0.0482(13) Uani 0.412(3) 1 d G U P A 1
C2A_1 C 0.4977(4) 0.4833(5) 0.2452(3) 0.0523(12) Uani 0.412(3) 1 d G U P A 1
C3A_1 C 0.4434(3) 0.5241(4) 0.2598(3) 0.0658(12) Uani 0.412(3) 1 d G U P A 1
C4A_1 C 0.4317(3) 0.5423(4) 0.3182(4) 0.0686(13) Uani 0.412(3) 1 d G U P A 1
C5A_1 C 0.4743(4) 0.5197(4) 0.3620(3) 0.0659(14) Uani 0.412(3) 1 d G U P A 1
C6A_1 C 0.5286(3) 0.4788(5) 0.3474(3) 0.0585(13) Uani 0.412(3) 1 d G U P A 1
F2A_1 F 0.5652(3) 0.4592(3) 0.3927(3) 0.0474(14) Uani 0.412(3) 1 d . U P A 1
F3A_1 F 0.5065(4) 0.4677(4) 0.1924(4) 0.0656(19) Uani 0.412(3) 1 d . U P A 1
F4A_1 F 0.4032(3) 0.5465(3) 0.2207(4) 0.0921(17) Uani 0.412(3) 1 d . U P A 1
F5A_1 F 0.4614(3) 0.5400(4) 0.4195(4) 0.092(2) Uani 0.412(3) 1 d . U P A 1
F6A_1 F 0.3791(3) 0.5823(3) 0.3351(4) 0.1001(17) Uani 0.412(3) 1 d . U P A 1
C1B_1 C 0.5361(2) 0.4616(3) 0.2774(2) 0.0478(11) Uani 0.588(3) 1 d G U P A 2
C2B_1 C 0.5069(3) 0.4778(3) 0.2238(2) 0.0540(12) Uani 0.588(3) 1 d G U P A 2
C3B_1 C 0.4517(2) 0.5208(3) 0.2222(2) 0.0613(12) Uani 0.588(3) 1 d G U P A 2
C4B_1 C 0.42565(19) 0.5477(2) 0.2742(3) 0.0706(12) Uani 0.588(3) 1 d G U P A 2
C5B_1 C 0.4548(2) 0.5316(3) 0.3278(2) 0.0690(12) Uani 0.588(3) 1 d G U P A 2
C6B_1 C 0.5101(2) 0.4885(3) 0.3294(2) 0.0561(10) Uani 0.588(3) 1 d G U P A 2
F2B_1 F 0.5357(3) 0.4758(3) 0.3794(2) 0.0662(13) Uani 0.588(3) 1 d . U P A 2
F3B_1 F 0.5281(2) 0.4543(3) 0.17324(19) 0.0447(10) Uani 0.588(3) 1 d . U P A 2
F4B_1 F 0.4219(2) 0.5378(2) 0.1715(3) 0.0839(14) Uani 0.588(3) 1 d . U P A 2
F5B_1 F 0.4311(3) 0.5588(3) 0.3768(3) 0.1009(15) Uani 0.588(3) 1 d . U P A 2
F6B_1 F 0.3733(2) 0.5916(2) 0.2735(3) 0.1051(15) Uani 0.588(3) 1 d . U P A 2
F1_1 F 0.69341(8) 0.35566(9) 0.27352(7) 0.0446(4) Uani 1 1 d . . . . .
C1_2 C 0.66502(13) 0.48827(14) 0.24970(11) 0.0303(6) Uani 1 1 d . . . . .
N1_2 N 0.68894(13) 0.50412(14) 0.19542(10) 0.0443(6) Uani 1 1 d . . . . .
C2_2 C 0.7351(2) 0.5819(2) 0.25364(15) 0.0711(13) Uani 1 1 d . . . . .
H2_2 H 0.7606 0.6200 0.2690 0.085 Uiso 1 1 calc R U . . .
N2_2 N 0.69407(12) 0.53763(13) 0.28496(10) 0.0391(6) Uani 1 1 d . . . . .
C3_2 C 0.7320(2) 0.5610(2) 0.19789(15) 0.0762(14) Uani 1 1 d . . . . .
H3_2 H 0.7550 0.5814 0.1657 0.091 Uiso 1 1 calc R U . . .
C4_2 C 0.67091(15) 0.47338(16) 0.13926(11) 0.0395(7) Uani 1 1 d . . . . .
C5_2 C 0.70289(15) 0.41300(18) 0.11903(12) 0.0440(7) Uani 1 1 d . . . . .
C6_2 C 0.68562(16) 0.38758(18) 0.06378(13) 0.0472(8) Uani 1 1 d . . . . .
H6_2 H 0.7065 0.3458 0.0490 0.057 Uiso 1 1 calc R U . . .
C7_2 C 0.63919(17) 0.42087(18) 0.02963(12) 0.0462(8) Uani 1 1 d . . . . .
C8_2 C 0.60987(18) 0.48193(18) 0.05058(13) 0.0503(8) Uani 1 1 d . . . . .
H8_2 H 0.5784 0.5057 0.0269 0.060 Uiso 1 1 calc R U . . .
C9_2 C 0.62522(17) 0.50989(17) 0.10573(13) 0.0461(8) Uani 1 1 d . . . . .
C10_2 C 0.75676(17) 0.3782(2) 0.15403(14) 0.0646(11) Uani 1 1 d . . . . .
H10A_2 H 0.7717 0.3349 0.1336 0.097 Uiso 1 1 calc R U . . .
H10B_2 H 0.7404 0.3652 0.1931 0.097 Uiso 1 1 calc R U . . .
H10C_2 H 0.7931 0.4118 0.1581 0.097 Uiso 1 1 calc R U . . .
C11_2 C 0.6217(2) 0.3910(2) -0.03047(14) 0.0659(11) Uani 1 1 d . . . . .
H11A_2 H 0.5826 0.4153 -0.0453 0.099 Uiso 1 1 calc R U . . .
H11B_2 H 0.6132 0.3395 -0.0272 0.099 Uiso 1 1 calc R U . . .
H11C_2 H 0.6579 0.3991 -0.0578 0.099 Uiso 1 1 calc R U . . .
C12_2 C 0.5936(2) 0.57865(18) 0.12614(16) 0.0653(11) Uani 1 1 d . . . . .
H12A_2 H 0.6208 0.6195 0.1146 0.098 Uiso 1 1 calc R U . . .
H12B_2 H 0.5891 0.5778 0.1691 0.098 Uiso 1 1 calc R U . . .
H12C_2 H 0.5505 0.5832 0.1080 0.098 Uiso 1 1 calc R U . . .
C13_2 C 0.68120(14) 0.54775(14) 0.34689(11) 0.0333(6) Uani 1 1 d . . . . .
C14_2 C 0.63533(15) 0.59908(15) 0.36268(13) 0.0393(7) Uani 1 1 d . . . . .
C15_2 C 0.62381(15) 0.60937(18) 0.42231(14) 0.0488(8) Uani 1 1 d . . . . .
H15_2 H 0.5926 0.6441 0.4343 0.059 Uiso 1 1 calc R U . . .
C16_2 C 0.65665(15) 0.5703(2) 0.46452(13) 0.0516(9) Uani 1 1 d . . . . .
C17_2 C 0.70306(15) 0.52126(19) 0.44683(13) 0.0469(8) Uani 1 1 d . . . . .
H17_2 H 0.7264 0.4952 0.4759 0.056 Uiso 1 1 calc R U . . .
C18_2 C 0.71680(13) 0.50879(16) 0.38764(12) 0.0356(6) Uani 1 1 d . . . . .
C19_2 C 0.76842(16) 0.45667(19) 0.36938(15) 0.0514(8) Uani 1 1 d . . . . .
H19A_2 H 0.8017 0.4817 0.3462 0.077 Uiso 1 1 calc R U . . .
H19B_2 H 0.7488 0.4186 0.3455 0.077 Uiso 1 1 calc R U . . .
H19C_2 H 0.7886 0.4356 0.4045 0.077 Uiso 1 1 calc R U . . .
C20_2 C 0.59885(18) 0.64206(18) 0.31749(16) 0.0569(9) Uani 1 1 d . . . . .
H20A_2 H 0.5779 0.6095 0.2894 0.085 Uiso 1 1 calc R U . . .
H20B_2 H 0.6293 0.6735 0.2965 0.085 Uiso 1 1 calc R U . . .
H20C_2 H 0.5656 0.6712 0.3371 0.085 Uiso 1 1 calc R U . . .
C21_2 C 0.6410(2) 0.5799(3) 0.52923(15) 0.0885(16) Uani 1 1 d . . . . .
H21A_2 H 0.6430 0.6310 0.5394 0.133 Uiso 1 1 calc R U . . .
H21B_2 H 0.6727 0.5533 0.5530 0.133 Uiso 1 1 calc R U . . .
H21C_2 H 0.5971 0.5616 0.5372 0.133 Uiso 1 1 calc R U . . .
C1_3 C 0.57358(13) 0.32028(14) 0.30245(11) 0.0305(6) Uani 1 1 d . . . . .
N1_3 N 0.52971(12) 0.28107(12) 0.27107(10) 0.0372(5) Uani 1 1 d . . . . .
C2_3 C 0.51403(19) 0.21781(17) 0.29918(15) 0.0564(10) Uani 1 1 d . . . . .
H2_3 H 0.4849 0.1819 0.2854 0.068 Uiso 1 1 calc R U . . .
N2_3 N 0.58355(12) 0.27934(12) 0.35133(10) 0.0369(6) Uani 1 1 d . . . . .
C3_3 C 0.54740(19) 0.21672(18) 0.34920(15) 0.0571(10) Uani 1 1 d . . . . .
H3_3 H 0.5466 0.1799 0.3781 0.069 Uiso 1 1 calc R U . . .
C4_3 C 0.62533(14) 0.29489(14) 0.40086(11) 0.0327(6) Uani 1 1 d . . . . .
C5_3 C 0.59828(16) 0.32520(16) 0.45106(13) 0.0421(7) Uani 1 1 d . . . . .
C6_3 C 0.63937(19) 0.33776(18) 0.49857(13) 0.0535(9) Uani 1 1 d . . . . .
H6_3 H 0.6222 0.3602 0.5327 0.064 Uiso 1 1 calc R U . . .
C7_3 C 0.70416(19) 0.31869(19) 0.49776(14) 0.0530(9) Uani 1 1 d . . . . .
C8_3 C 0.72792(16) 0.28507(19) 0.44859(14) 0.0503(8) Uani 1 1 d . . . . .
H8_3 H 0.7722 0.2704 0.4481 0.060 Uiso 1 1 calc R U . . .
C9_3 C 0.68957(15) 0.27174(15) 0.39964(12) 0.0381(7) Uani 1 1 d . . . . .
C10_3 C 0.52630(18) 0.3408(2) 0.45596(18) 0.0721(12) Uani 1 1 d . . . . .
H10A_3 H 0.5199 0.3869 0.4758 0.108 Uiso 1 1 calc R U . . .
H10B_3 H 0.5052 0.3027 0.4788 0.108 Uiso 1 1 calc R U . . .
H10C_3 H 0.5071 0.3428 0.4165 0.108 Uiso 1 1 calc R U . . .
C11_3 C 0.7476(2) 0.3348(3) 0.54982(17) 0.0894(15) Uani 1 1 d . . . . .
H11A_3 H 0.7838 0.3005 0.5507 0.134 Uiso 1 1 calc R U . . .
H11B_3 H 0.7223 0.3306 0.5863 0.134 Uiso 1 1 calc R U . . .
H11C_3 H 0.7648 0.3837 0.5463 0.134 Uiso 1 1 calc R U . . .
C12_3 C 0.7167(2) 0.2298(2) 0.34854(14) 0.0615(10) Uani 1 1 d . . . . .
H12A_3 H 0.6897 0.1872 0.3417 0.092 Uiso 1 1 calc R U . . .
H12B_3 H 0.7614 0.2150 0.3575 0.092 Uiso 1 1 calc R U . . .
H12C_3 H 0.7166 0.2599 0.3132 0.092 Uiso 1 1 calc R U . . .
C13_3 C 0.50493(14) 0.29835(14) 0.21313(12) 0.0342(6) Uani 1 1 d . . . . .
C14_3 C 0.44116(15) 0.32229(15) 0.20771(13) 0.0383(7) Uani 1 1 d . . . . .
C15_3 C 0.41784(16) 0.33474(15) 0.15148(14) 0.0433(7) Uani 1 1 d . . . . .
H15_3 H 0.3744 0.3514 0.1467 0.052 Uiso 1 1 calc R U . . .
C16_3 C 0.45587(17) 0.32364(17) 0.10217(14) 0.0469(8) Uani 1 1 d . . . . .
C17_3 C 0.51875(16) 0.29881(17) 0.10938(13) 0.0449(7) Uani 1 1 d . . . . .
H17_3 H 0.5449 0.2907 0.0755 0.054 Uiso 1 1 calc R U . . .
C18_3 C 0.54492(15) 0.28537(15) 0.16463(13) 0.0379(7) Uani 1 1 d . . . . .
C19_3 C 0.61294(16) 0.25672(19) 0.17131(16) 0.0536(8) Uani 1 1 d . . . . .
H19A_3 H 0.6316 0.2478 0.1323 0.080 Uiso 1 1 calc R U . . .
H19B_3 H 0.6118 0.2118 0.1937 0.080 Uiso 1 1 calc R U . . .
H19C_3 H 0.6397 0.2919 0.1923 0.080 Uiso 1 1 calc R U . . .
C20_3 C 0.39800(17) 0.33446(19) 0.26057(15) 0.0536(9) Uani 1 1 d . . . . .
H20A_3 H 0.3574 0.3575 0.2480 0.080 Uiso 1 1 calc R U . . .
H20B_3 H 0.4205 0.3655 0.2888 0.080 Uiso 1 1 calc R U . . .
H20C_3 H 0.3881 0.2883 0.2792 0.080 Uiso 1 1 calc R U . . .
C21_3 C 0.4295(2) 0.3381(2) 0.04089(16) 0.0740(12) Uani 1 1 d . . . . .
H21A_3 H 0.4651 0.3542 0.0153 0.111 Uiso 1 1 calc R U . . .
H21B_3 H 0.3960 0.3754 0.0429 0.111 Uiso 1 1 calc R U . . .
H21C_3 H 0.4105 0.2939 0.0249 0.111 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 F1_1 1.8442(17) . ?
Ni1 C1A_1 1.882(4) . ?
Ni1 C1_3 1.922(3) . ?
Ni1 C1_2 1.923(3) . ?
Ni1 C1B_1 1.943(3) . ?
C1A_1 C2A_1 1.3900 . ?
C1A_1 C6A_1 1.3900 . ?
C2A_1 F3A_1 1.247(10) . ?
C2A_1 C3A_1 1.3900 . ?
C3A_1 F4A_1 1.283(9) . ?
C3A_1 C4A_1 1.3900 . ?
C4A_1 F6A_1 1.367(7) . ?
C4A_1 C5A_1 1.3900 . ?
C5A_1 F5A_1 1.387(9) . ?
C5A_1 C6A_1 1.3900 . ?
C6A_1 F2A_1 1.327(9) . ?
C1B_1 C2B_1 1.3900 . ?
C1B_1 C6B_1 1.3900 . ?
C2B_1 F3B_1 1.305(5) . ?
C2B_1 C3B_1 1.3900 . ?
C3B_1 F4B_1 1.343(6) . ?
C3B_1 C4B_1 1.3900 . ?
C4B_1 F6B_1 1.350(5) . ?
C4B_1 C5B_1 1.3900 . ?
C5B_1 F5B_1 1.317(6) . ?
C5B_1 C6B_1 1.3900 . ?
C6B_1 F2B_1 1.275(7) . ?
C1_2 N2_2 1.358(3) . ?
C1_2 N1_2 1.360(3) . ?
N1_2 C3_2 1.382(4) . ?
N1_2 C4_2 1.447(3) . ?
C2_2 C3_2 1.326(5) . ?
C2_2 N2_2 1.376(4) . ?
C2_2 H2_2 0.9500 . ?
N2_2 C13_2 1.444(3) . ?
C3_2 H3_2 0.9500 . ?
C4_2 C5_2 1.382(4) . ?
C4_2 C9_2 1.387(4) . ?
C5_2 C6_2 1.388(4) . ?
C5_2 C10_2 1.509(5) . ?
C6_2 C7_2 1.377(5) . ?
C6_2 H6_2 0.9500 . ?
C7_2 C8_2 1.373(5) . ?
C7_2 C11_2 1.517(4) . ?
C8_2 C9_2 1.393(4) . ?
C8_2 H8_2 0.9500 . ?
C9_2 C12_2 1.509(5) . ?
C10_2 H10A_2 0.9800 . ?
C10_2 H10B_2 0.9800 . ?
C10_2 H10C_2 0.9800 . ?
C11_2 H11A_2 0.9800 . ?
C11_2 H11B_2 0.9800 . ?
C11_2 H11C_2 0.9800 . ?
C12_2 H12A_2 0.9800 . ?
C12_2 H12B_2 0.9800 . ?
C12_2 H12C_2 0.9800 . ?
C13_2 C18_2 1.385(4) . ?
C13_2 C14_2 1.390(4) . ?
C14_2 C15_2 1.388(4) . ?
C14_2 C20_2 1.502(4) . ?
C15_2 C16_2 1.380(5) . ?
C15_2 H15_2 0.9500 . ?
C16_2 C17_2 1.381(5) . ?
C16_2 C21_2 1.515(4) . ?
C17_2 C18_2 1.394(4) . ?
C17_2 H17_2 0.9500 . ?
C18_2 C19_2 1.496(4) . ?
C19_2 H19A_2 0.9800 . ?
C19_2 H19B_2 0.9800 . ?
C19_2 H19C_2 0.9800 . ?
C20_2 H20A_2 0.9800 . ?
C20_2 H20B_2 0.9800 . ?
C20_2 H20C_2 0.9800 . ?
C21_2 H21A_2 0.9800 . ?
C21_2 H21B_2 0.9800 . ?
C21_2 H21C_2 0.9800 . ?
C1_3 N1_3 1.362(3) . ?
C1_3 N2_3 1.363(3) . ?
N1_3 C2_3 1.379(4) . ?
N1_3 C13_3 1.447(3) . ?
C2_3 C3_3 1.327(4) . ?
C2_3 H2_3 0.9500 . ?
N2_3 C3_3 1.384(4) . ?
N2_3 C4_3 1.444(3) . ?
C3_3 H3_3 0.9500 . ?
C4_3 C9_3 1.388(4) . ?
C4_3 C5_3 1.389(4) . ?
C5_3 C6_3 1.390(5) . ?
C5_3 C10_3 1.511(5) . ?
C6_3 C7_3 1.377(5) . ?
C6_3 H6_3 0.9500 . ?
C7_3 C8_3 1.371(5) . ?
C7_3 C11_3 1.511(5) . ?
C8_3 C9_3 1.385(4) . ?
C8_3 H8_3 0.9500 . ?
C9_3 C12_3 1.506(4) . ?
C10_3 H10A_3 0.9800 . ?
C10_3 H10B_3 0.9800 . ?
C10_3 H10C_3 0.9800 . ?
C11_3 H11A_3 0.9800 . ?
C11_3 H11B_3 0.9800 . ?
C11_3 H11C_3 0.9800 . ?
C12_3 H12A_3 0.9800 . ?
C12_3 H12B_3 0.9800 . ?
C12_3 H12C_3 0.9800 . ?
C13_3 C14_3 1.389(4) . ?
C13_3 C18_3 1.395(4) . ?
C14_3 C15_3 1.384(4) . ?
C14_3 C20_3 1.510(4) . ?
C15_3 C16_3 1.381(5) . ?
C15_3 H15_3 0.9500 . ?
C16_3 C17_3 1.382(5) . ?
C16_3 C21_3 1.517(4) . ?
C17_3 C18_3 1.388(4) . ?
C17_3 H17_3 0.9500 . ?
C18_3 C19_3 1.503(4) . ?
C19_3 H19A_3 0.9800 . ?
C19_3 H19B_3 0.9800 . ?
C19_3 H19C_3 0.9800 . ?
C20_3 H20A_3 0.9800 . ?
C20_3 H20B_3 0.9800 . ?
C20_3 H20C_3 0.9800 . ?
C21_3 H21A_3 0.9800 . ?
C21_3 H21B_3 0.9800 . ?
C21_3 H21C_3 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
F1_1 Ni1 C1A_1 173.7(3) . . ?
F1_1 Ni1 C1_3 88.59(9) . . ?
C1A_1 Ni1 C1_3 91.3(3) . . ?
F1_1 Ni1 C1_2 87.11(10) . . ?
C1A_1 Ni1 C1_2 93.0(3) . . ?
C1_3 Ni1 C1_2 175.59(11) . . ?
F1_1 Ni1 C1B_1 177.80(19) . . ?
C1_3 Ni1 C1B_1 92.9(2) . . ?
C1_2 Ni1 C1B_1 91.4(2) . . ?
C2A_1 C1A_1 C6A_1 120.0 . . ?
C2A_1 C1A_1 Ni1 125.6(4) . . ?
C6A_1 C1A_1 Ni1 114.4(4) . . ?
F3A_1 C2A_1 C1A_1 121.7(6) . . ?
F3A_1 C2A_1 C3A_1 118.3(6) . . ?
C1A_1 C2A_1 C3A_1 120.0 . . ?
F4A_1 C3A_1 C4A_1 118.1(7) . . ?
F4A_1 C3A_1 C2A_1 121.9(7) . . ?
C4A_1 C3A_1 C2A_1 120.0 . . ?
F6A_1 C4A_1 C3A_1 122.5(7) . . ?
F6A_1 C4A_1 C5A_1 117.5(7) . . ?
C3A_1 C4A_1 C5A_1 120.0 . . ?
F5A_1 C5A_1 C6A_1 121.8(6) . . ?
F5A_1 C5A_1 C4A_1 118.1(6) . . ?
C6A_1 C5A_1 C4A_1 120.0 . . ?
F2A_1 C6A_1 C5A_1 114.9(5) . . ?
F2A_1 C6A_1 C1A_1 125.1(5) . . ?
C5A_1 C6A_1 C1A_1 120.0 . . ?
C2B_1 C1B_1 C6B_1 120.0 . . ?
C2B_1 C1B_1 Ni1 118.4(3) . . ?
C6B_1 C1B_1 Ni1 121.5(3) . . ?
F3B_1 C2B_1 C3B_1 116.3(4) . . ?
F3B_1 C2B_1 C1B_1 123.7(4) . . ?
C3B_1 C2B_1 C1B_1 120.0 . . ?
F4B_1 C3B_1 C4B_1 118.0(4) . . ?
F4B_1 C3B_1 C2B_1 122.0(4) . . ?
C4B_1 C3B_1 C2B_1 120.0 . . ?
F6B_1 C4B_1 C3B_1 120.9(5) . . ?
F6B_1 C4B_1 C5B_1 119.1(5) . . ?
C3B_1 C4B_1 C5B_1 120.0 . . ?
F5B_1 C5B_1 C4B_1 119.8(5) . . ?
F5B_1 C5B_1 C6B_1 120.2(5) . . ?
C4B_1 C5B_1 C6B_1 120.0 . . ?
F2B_1 C6B_1 C5B_1 117.9(4) . . ?
F2B_1 C6B_1 C1B_1 122.1(4) . . ?
C5B_1 C6B_1 C1B_1 120.0 . . ?
N2_2 C1_2 N1_2 103.2(2) . . ?
N2_2 C1_2 Ni1 125.14(19) . . ?
N1_2 C1_2 Ni1 130.57(19) . . ?
C1_2 N1_2 C3_2 111.2(2) . . ?
C1_2 N1_2 C4_2 128.4(2) . . ?
C3_2 N1_2 C4_2 120.2(2) . . ?
C3_2 C2_2 N2_2 106.8(3) . . ?
C3_2 C2_2 H2_2 126.6 . . ?
N2_2 C2_2 H2_2 126.6 . . ?
C1_2 N2_2 C2_2 111.7(2) . . ?
C1_2 N2_2 C13_2 125.6(2) . . ?
C2_2 N2_2 C13_2 122.5(2) . . ?
C2_2 C3_2 N1_2 107.1(3) . . ?
C2_2 C3_2 H3_2 126.5 . . ?
N1_2 C3_2 H3_2 126.5 . . ?
C5_2 C4_2 C9_2 122.6(3) . . ?
C5_2 C4_2 N1_2 119.6(3) . . ?
C9_2 C4_2 N1_2 117.6(3) . . ?
C4_2 C5_2 C6_2 117.2(3) . . ?
C4_2 C5_2 C10_2 121.6(3) . . ?
C6_2 C5_2 C10_2 121.1(3) . . ?
C7_2 C6_2 C5_2 122.2(3) . . ?
C7_2 C6_2 H6_2 118.9 . . ?
C5_2 C6_2 H6_2 118.9 . . ?
C8_2 C7_2 C6_2 118.8(3) . . ?
C8_2 C7_2 C11_2 120.8(3) . . ?
C6_2 C7_2 C11_2 120.4(3) . . ?
C7_2 C8_2 C9_2 121.5(3) . . ?
C7_2 C8_2 H8_2 119.2 . . ?
C9_2 C8_2 H8_2 119.2 . . ?
C4_2 C9_2 C8_2 117.6(3) . . ?
C4_2 C9_2 C12_2 122.6(3) . . ?
C8_2 C9_2 C12_2 119.8(3) . . ?
C5_2 C10_2 H10A_2 109.5 . . ?
C5_2 C10_2 H10B_2 109.5 . . ?
H10A_2 C10_2 H10B_2 109.5 . . ?
C5_2 C10_2 H10C_2 109.5 . . ?
H10A_2 C10_2 H10C_2 109.5 . . ?
H10B_2 C10_2 H10C_2 109.5 . . ?
C7_2 C11_2 H11A_2 109.5 . . ?
C7_2 C11_2 H11B_2 109.5 . . ?
H11A_2 C11_2 H11B_2 109.5 . . ?
C7_2 C11_2 H11C_2 109.5 . . ?
H11A_2 C11_2 H11C_2 109.5 . . ?
H11B_2 C11_2 H11C_2 109.5 . . ?
C9_2 C12_2 H12A_2 109.5 . . ?
C9_2 C12_2 H12B_2 109.5 . . ?
H12A_2 C12_2 H12B_2 109.5 . . ?
C9_2 C12_2 H12C_2 109.5 . . ?
H12A_2 C12_2 H12C_2 109.5 . . ?
H12B_2 C12_2 H12C_2 109.5 . . ?
C18_2 C13_2 C14_2 123.1(2) . . ?
C18_2 C13_2 N2_2 119.1(3) . . ?
C14_2 C13_2 N2_2 117.7(3) . . ?
C15_2 C14_2 C13_2 117.5(3) . . ?
C15_2 C14_2 C20_2 120.6(3) . . ?
C13_2 C14_2 C20_2 121.9(3) . . ?
C16_2 C15_2 C14_2 121.5(3) . . ?
C16_2 C15_2 H15_2 119.3 . . ?
C14_2 C15_2 H15_2 119.3 . . ?
C15_2 C16_2 C17_2 119.0(3) . . ?
C15_2 C16_2 C21_2 120.6(3) . . ?
C17_2 C16_2 C21_2 120.5(3) . . ?
C16_2 C17_2 C18_2 122.1(3) . . ?
C16_2 C17_2 H17_2 119.0 . . ?
C18_2 C17_2 H17_2 119.0 . . ?
C13_2 C18_2 C17_2 116.8(3) . . ?
C13_2 C18_2 C19_2 121.9(3) . . ?
C17_2 C18_2 C19_2 121.3(3) . . ?
C18_2 C19_2 H19A_2 109.5 . . ?
C18_2 C19_2 H19B_2 109.5 . . ?
H19A_2 C19_2 H19B_2 109.5 . . ?
C18_2 C19_2 H19C_2 109.5 . . ?
H19A_2 C19_2 H19C_2 109.5 . . ?
H19B_2 C19_2 H19C_2 109.5 . . ?
C14_2 C20_2 H20A_2 109.5 . . ?
C14_2 C20_2 H20B_2 109.5 . . ?
H20A_2 C20_2 H20B_2 109.5 . . ?
C14_2 C20_2 H20C_2 109.5 . . ?
H20A_2 C20_2 H20C_2 109.5 . . ?
H20B_2 C20_2 H20C_2 109.5 . . ?
C16_2 C21_2 H21A_2 109.5 . . ?
C16_2 C21_2 H21B_2 109.5 . . ?
H21A_2 C21_2 H21B_2 109.5 . . ?
C16_2 C21_2 H21C_2 109.5 . . ?
H21A_2 C21_2 H21C_2 109.5 . . ?
H21B_2 C21_2 H21C_2 109.5 . . ?
N1_3 C1_3 N2_3 103.0(2) . . ?
N1_3 C1_3 Ni1 126.39(19) . . ?
N2_3 C1_3 Ni1 130.2(2) . . ?
C1_3 N1_3 C2_3 111.8(2) . . ?
C1_3 N1_3 C13_3 126.1(2) . . ?
C2_3 N1_3 C13_3 122.0(2) . . ?
C3_3 C2_3 N1_3 106.8(3) . . ?
C3_3 C2_3 H2_3 126.6 . . ?
N1_3 C2_3 H2_3 126.6 . . ?
C1_3 N2_3 C3_3 111.3(2) . . ?
C1_3 N2_3 C4_3 127.7(2) . . ?
C3_3 N2_3 C4_3 121.0(2) . . ?
C2_3 C3_3 N2_3 107.1(3) . . ?
C2_3 C3_3 H3_3 126.4 . . ?
N2_3 C3_3 H3_3 126.4 . . ?
C9_3 C4_3 C5_3 121.5(3) . . ?
C9_3 C4_3 N2_3 119.1(2) . . ?
C5_3 C4_3 N2_3 118.9(3) . . ?
C4_3 C5_3 C6_3 117.6(3) . . ?
C4_3 C5_3 C10_3 122.0(3) . . ?
C6_3 C5_3 C10_3 120.3(3) . . ?
C7_3 C6_3 C5_3 122.2(3) . . ?
C7_3 C6_3 H6_3 118.9 . . ?
C5_3 C6_3 H6_3 118.9 . . ?
C8_3 C7_3 C6_3 118.2(3) . . ?
C8_3 C7_3 C11_3 121.2(4) . . ?
C6_3 C7_3 C11_3 120.6(4) . . ?
C7_3 C8_3 C9_3 122.3(3) . . ?
C7_3 C8_3 H8_3 118.9 . . ?
C9_3 C8_3 H8_3 118.9 . . ?
C8_3 C9_3 C4_3 117.9(3) . . ?
C8_3 C9_3 C12_3 120.1(3) . . ?
C4_3 C9_3 C12_3 121.9(3) . . ?
C5_3 C10_3 H10A_3 109.5 . . ?
C5_3 C10_3 H10B_3 109.5 . . ?
H10A_3 C10_3 H10B_3 109.5 . . ?
C5_3 C10_3 H10C_3 109.5 . . ?
H10A_3 C10_3 H10C_3 109.5 . . ?
H10B_3 C10_3 H10C_3 109.5 . . ?
C7_3 C11_3 H11A_3 109.5 . . ?
C7_3 C11_3 H11B_3 109.5 . . ?
H11A_3 C11_3 H11B_3 109.5 . . ?
C7_3 C11_3 H11C_3 109.5 . . ?
H11A_3 C11_3 H11C_3 109.5 . . ?
H11B_3 C11_3 H11C_3 109.5 . . ?
C9_3 C12_3 H12A_3 109.5 . . ?
C9_3 C12_3 H12B_3 109.5 . . ?
H12A_3 C12_3 H12B_3 109.5 . . ?
C9_3 C12_3 H12C_3 109.5 . . ?
H12A_3 C12_3 H12C_3 109.5 . . ?
H12B_3 C12_3 H12C_3 109.5 . . ?
C14_3 C13_3 C18_3 122.7(3) . . ?
C14_3 C13_3 N1_3 118.9(3) . . ?
C18_3 C13_3 N1_3 118.2(3) . . ?
C15_3 C14_3 C13_3 117.5(3) . . ?
C15_3 C14_3 C20_3 120.4(3) . . ?
C13_3 C14_3 C20_3 122.1(3) . . ?
C16_3 C15_3 C14_3 121.9(3) . . ?
C16_3 C15_3 H15_3 119.1 . . ?
C14_3 C15_3 H15_3 119.1 . . ?
C15_3 C16_3 C17_3 118.8(3) . . ?
C15_3 C16_3 C21_3 121.1(3) . . ?
C17_3 C16_3 C21_3 120.1(3) . . ?
C16_3 C17_3 C18_3 122.0(3) . . ?
C16_3 C17_3 H17_3 119.0 . . ?
C18_3 C17_3 H17_3 119.0 . . ?
C17_3 C18_3 C13_3 117.1(3) . . ?
C17_3 C18_3 C19_3 121.0(3) . . ?
C13_3 C18_3 C19_3 121.9(3) . . ?
C18_3 C19_3 H19A_3 109.5 . . ?
C18_3 C19_3 H19B_3 109.5 . . ?
H19A_3 C19_3 H19B_3 109.5 . . ?
C18_3 C19_3 H19C_3 109.5 . . ?
H19A_3 C19_3 H19C_3 109.5 . . ?
H19B_3 C19_3 H19C_3 109.5 . . ?
C14_3 C20_3 H20A_3 109.5 . . ?
C14_3 C20_3 H20B_3 109.5 . . ?
H20A_3 C20_3 H20B_3 109.5 . . ?
C14_3 C20_3 H20C_3 109.5 . . ?
H20A_3 C20_3 H20C_3 109.5 . . ?
H20B_3 C20_3 H20C_3 109.5 . . ?
C16_3 C21_3 H21A_3 109.5 . . ?
C16_3 C21_3 H21B_3 109.5 . . ?
H21A_3 C21_3 H21B_3 109.5 . . ?
C16_3 C21_3 H21C_3 109.5 . . ?
H21A_3 C21_3 H21C_3 109.5 . . ?
H21B_3 C21_3 H21C_3 109.5 . . ?

_refine_diff_density_max         0.535
_refine_diff_density_min         -0.497
_refine_diff_density_rms         0.056

####################################################################### 
# 
# 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_Compound_9
_database_code_depnum_ccdc_archive 'CCDC 2017695'
loop_
_audit_author_name
_audit_author_address
'Udo Radius'
;University Wuerzburg
Germany
;
_audit_update_record             
;
2020-07-20 deposited with the CCDC.	2020-10-06 downloaded from the CCDC.
;


_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C42 H48 F2 N4 Ni'
_chemical_formula_sum            'C42 H48 F2 N4 Ni'
_chemical_formula_weight         705.55

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'
Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-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                   17.054(2)
_cell_length_b                   18.722(3)
_cell_length_c                   22.837(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     7291.4(17)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9666
_cell_measurement_theta_min      2.41
_cell_measurement_theta_max      26.21

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.285
_exptl_crystal_F_000             2992
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.302
_exptl_crystal_size_mid          0.256
_exptl_crystal_size_min          0.251
_exptl_absorpt_coefficient_mu    0.578
_shelx_estimated_absorpt_T_min   0.845
_shelx_estimated_absorpt_T_max   0.869
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5772
_exptl_absorpt_correction_T_max  0.6904
_exptl_absorpt_process_details   
'SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'rotating anode'
_diffrn_measurement_device_type  'Bruker X8-APEX II'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            96913
_diffrn_reflns_av_unetI/netI     0.0654
_diffrn_reflns_av_R_equivalents  0.1308
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         2.176
_diffrn_reflns_theta_max         27.173
_diffrn_reflns_theta_full        26.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             8064
_reflns_number_gt                5785
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0993P)²+5.3609P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         8064
_refine_ls_number_parameters     454
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0891
_refine_ls_R_factor_gt           0.0576
_refine_ls_wR_factor_ref         0.1766
_refine_ls_wR_factor_gt          0.1478
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_restrained_S_all      1.051
_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 0.37420(2) 0.64148(2) 0.66200(2) 0.01433(13) Uani 1 1 d . . . . .
F1_1 F 0.47813(10) 0.65434(9) 0.67748(8) 0.0247(4) Uani 1 1 d . . . . .
F2_1 F 0.26914(11) 0.62818(10) 0.64613(9) 0.0273(4) Uani 1 1 d . . . . .
C1_2 C 0.39159(16) 0.54243(16) 0.64859(13) 0.0182(6) Uani 1 1 d . . . . .
N1_2 N 0.37707(14) 0.50435(13) 0.59943(11) 0.0195(5) Uani 1 1 d . . . . .
C2_2 C 0.4206(2) 0.42566(17) 0.66261(14) 0.0265(7) Uani 1 1 d . . . . .
H2_2 H 0.437381 0.382822 0.681075 0.032 Uiso 1 1 calc R U . . .
N2_2 N 0.41843(15) 0.49336(13) 0.68743(11) 0.0197(5) Uani 1 1 d . . . . .
C3_2 C 0.3944(2) 0.43253(17) 0.60745(15) 0.0271(7) Uani 1 1 d . . . . .
H3_2 H 0.388888 0.395454 0.579352 0.032 Uiso 1 1 calc R U . . .
C4_2 C 0.43649(17) 0.50849(15) 0.74765(13) 0.0188(6) Uani 1 1 d . . . . .
C5_2 C 0.51448(18) 0.51634(17) 0.76458(15) 0.0243(7) Uani 1 1 d . . . . .
C6_2 C 0.5297(2) 0.52873(18) 0.82349(16) 0.0293(8) Uani 1 1 d . . . . .
H6_2 H 0.582163 0.536444 0.835854 0.035 Uiso 1 1 calc R U . . .
C7_2 C 0.4695(2) 0.53011(17) 0.86490(15) 0.0293(8) Uani 1 1 d . . . . .
C8_2 C 0.39268(19) 0.52414(17) 0.84598(14) 0.0239(7) Uani 1 1 d . . . . .
H8_2 H 0.351461 0.526539 0.873887 0.029 Uiso 1 1 calc R U . . .
C9_2 C 0.37433(17) 0.51474(16) 0.78729(13) 0.0187(6) Uani 1 1 d . . . . .
C10_2 C 0.57933(19) 0.5130(2) 0.72020(18) 0.0363(9) Uani 1 1 d . . . . .
H10A_2 H 0.587294 0.463357 0.707998 0.054 Uiso 1 1 calc R U . . .
H10B_2 H 0.627794 0.531512 0.737563 0.054 Uiso 1 1 calc R U . . .
H10C_2 H 0.565219 0.542008 0.686055 0.054 Uiso 1 1 calc R U . . .
C11_2 C 0.4866(3) 0.5374(2) 0.92955(16) 0.0459(10) Uani 1 1 d . . . . .
H11A_2 H 0.537672 0.560537 0.934905 0.069 Uiso 1 1 calc R U . . .
H11B_2 H 0.487585 0.489941 0.947644 0.069 Uiso 1 1 calc R U . . .
H11C_2 H 0.445719 0.566441 0.948022 0.069 Uiso 1 1 calc R U . . .
C12_2 C 0.29034(17) 0.51355(18) 0.76692(14) 0.0246(7) Uani 1 1 d . . . . .
H12A_2 H 0.277130 0.559661 0.749162 0.037 Uiso 1 1 calc R U . . .
H12B_2 H 0.255770 0.504725 0.800425 0.037 Uiso 1 1 calc R U . . .
H12C_2 H 0.283461 0.475488 0.737907 0.037 Uiso 1 1 calc R U . . .
C13_2 C 0.35022(18) 0.53532(16) 0.54506(12) 0.0191(6) Uani 1 1 d . . . . .
C14_2 C 0.27251(18) 0.52582(17) 0.52846(14) 0.0229(7) Uani 1 1 d . . . . .
C15_2 C 0.24852(18) 0.55508(17) 0.47533(14) 0.0236(7) Uani 1 1 d . . . . .
H15_2 H 0.195582 0.549370 0.463262 0.028 Uiso 1 1 calc R U . . .
C16_2 C 0.30026(18) 0.59254(16) 0.43942(13) 0.0225(6) Uani 1 1 d . . . . .
C17_2 C 0.37744(17) 0.60068(16) 0.45790(13) 0.0208(6) Uani 1 1 d . . . . .
H17_2 H 0.413251 0.625385 0.433303 0.025 Uiso 1 1 calc R U . . .
C18_2 C 0.40423(17) 0.57375(17) 0.51150(13) 0.0211(6) Uani 1 1 d . . . . .
C19_2 C 0.2155(2) 0.4873(2) 0.56790(15) 0.0326(8) Uani 1 1 d . . . . .
H19A_2 H 0.163861 0.485659 0.549136 0.049 Uiso 1 1 calc R U . . .
H19B_2 H 0.211462 0.512795 0.605280 0.049 Uiso 1 1 calc R U . . .
H19C_2 H 0.234162 0.438579 0.574923 0.049 Uiso 1 1 calc R U . . .
C20_2 C 0.48637(18) 0.58725(18) 0.53250(14) 0.0247(7) Uani 1 1 d . . . . .
H20A_2 H 0.516139 0.611742 0.501765 0.037 Uiso 1 1 calc R U . . .
H20B_2 H 0.511714 0.541647 0.541736 0.037 Uiso 1 1 calc R U . . .
H20C_2 H 0.484852 0.617189 0.567680 0.037 Uiso 1 1 calc R U . . .
C21_2 C 0.2734(2) 0.62493(19) 0.38232(14) 0.0283(7) Uani 1 1 d . . . . .
H21A_2 H 0.315421 0.621109 0.353250 0.042 Uiso 1 1 calc R U . . .
H21B_2 H 0.260275 0.675357 0.388420 0.042 Uiso 1 1 calc R U . . .
H21C_2 H 0.226909 0.599361 0.368214 0.042 Uiso 1 1 calc R U . . .
C1_3 C 0.35515(16) 0.73985(16) 0.67714(12) 0.0166(6) Uani 1 1 d . . . . .
N1_3 N 0.31289(14) 0.76769(13) 0.72188(10) 0.0163(5) Uani 1 1 d . . . . .
C2_3 C 0.31229(19) 0.84196(17) 0.71956(14) 0.0233(7) Uani 1 1 d . . . . .
H2_3 H 0.286484 0.873257 0.746031 0.028 Uiso 1 1 calc R U . . .
N2_3 N 0.38077(14) 0.79795(13) 0.64736(11) 0.0162(5) Uani 1 1 d . . . . .
C3_3 C 0.3550(2) 0.86086(16) 0.67294(14) 0.0227(7) Uani 1 1 d . . . . .
H3_3 H 0.365509 0.908084 0.659923 0.027 Uiso 1 1 calc R U . . .
C4_3 C 0.43207(17) 0.79479(15) 0.59715(13) 0.0180(6) Uani 1 1 d . . . . .
C5_3 C 0.40093(18) 0.77607(16) 0.54270(13) 0.0209(6) Uani 1 1 d . . . . .
C6_3 C 0.45226(19) 0.77354(17) 0.49525(14) 0.0244(7) Uani 1 1 d . . . . .
H6_3 H 0.432238 0.761663 0.457669 0.029 Uiso 1 1 calc R U . . .
C7_3 C 0.53184(19) 0.78785(17) 0.50122(14) 0.0261(7) Uani 1 1 d . . . . .
C8_3 C 0.56038(18) 0.80590(17) 0.55631(14) 0.0240(7) Uani 1 1 d . . . . .
H8_3 H 0.614692 0.815784 0.560753 0.029 Uiso 1 1 calc R U . . .
C9_3 C 0.51164(18) 0.80993(16) 0.60521(14) 0.0211(6) Uani 1 1 d . . . . .
C10_3 C 0.31480(18) 0.75870(18) 0.53546(14) 0.0245(7) Uani 1 1 d . . . . .
H10A_3 H 0.302246 0.755039 0.493693 0.037 Uiso 1 1 calc R U . . .
H10B_3 H 0.283160 0.796645 0.553225 0.037 Uiso 1 1 calc R U . . .
H10C_3 H 0.303216 0.713162 0.554779 0.037 Uiso 1 1 calc R U . . .
C11_3 C 0.5877(2) 0.7818(2) 0.44988(16) 0.0378(9) Uani 1 1 d . . . . .
H11A_3 H 0.558727 0.788964 0.413279 0.057 Uiso 1 1 calc R U . . .
H11B_3 H 0.611771 0.734283 0.449777 0.057 Uiso 1 1 calc R U . . .
H11C_3 H 0.628656 0.818254 0.453368 0.057 Uiso 1 1 calc R U . . .
C12_3 C 0.54303(19) 0.82835(18) 0.66498(14) 0.0260(7) Uani 1 1 d . . . . .
H12A_3 H 0.600452 0.829504 0.663704 0.039 Uiso 1 1 calc R U . . .
H12B_3 H 0.525858 0.792229 0.693268 0.039 Uiso 1 1 calc R U . . .
H12C_3 H 0.523191 0.875294 0.676849 0.039 Uiso 1 1 calc R U . . .
C13_3 C 0.28016(17) 0.72763(15) 0.77018(12) 0.0173(6) Uani 1 1 d . . . . .
C14_3 C 0.20011(18) 0.71315(17) 0.77099(13) 0.0213(6) Uani 1 1 d . . . . .
C15_3 C 0.16909(18) 0.68064(17) 0.82079(15) 0.0246(7) Uani 1 1 d . . . . .
H15_3 H 0.114464 0.671009 0.822800 0.030 Uiso 1 1 calc R U . . .
C16_3 C 0.21737(18) 0.66208(16) 0.86769(14) 0.0224(7) Uani 1 1 d . . . . .
C17_3 C 0.29665(18) 0.67587(17) 0.86456(13) 0.0207(6) Uani 1 1 d . . . . .
H17_3 H 0.329264 0.662822 0.896545 0.025 Uiso 1 1 calc R U . . .
C18_3 C 0.33041(17) 0.70854(16) 0.81559(13) 0.0183(6) Uani 1 1 d . . . . .
C19_3 C 0.14914(19) 0.7296(2) 0.71868(15) 0.0299(8) Uani 1 1 d . . . . .
H19A_3 H 0.149200 0.781174 0.711469 0.045 Uiso 1 1 calc R U . . .
H19B_3 H 0.095430 0.713531 0.726414 0.045 Uiso 1 1 calc R U . . .
H19C_3 H 0.169696 0.704679 0.684196 0.045 Uiso 1 1 calc R U . . .
C20_3 C 0.41732(17) 0.72218(18) 0.81237(14) 0.0242(7) Uani 1 1 d . . . . .
H20A_3 H 0.439095 0.697884 0.778013 0.036 Uiso 1 1 calc R U . . .
H20B_3 H 0.442601 0.703879 0.847866 0.036 Uiso 1 1 calc R U . . .
H20C_3 H 0.426831 0.773652 0.809135 0.036 Uiso 1 1 calc R U . . .
C21_3 C 0.1822(2) 0.62723(19) 0.92173(16) 0.0327(8) Uani 1 1 d . . . . .
H21A_3 H 0.161664 0.579981 0.911424 0.049 Uiso 1 1 calc R U . . .
H21B_3 H 0.139466 0.657068 0.936765 0.049 Uiso 1 1 calc R U . . .
H21C_3 H 0.222711 0.622177 0.951869 0.049 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 F1_1 1.8233(18) . ?
Ni1 F2_1 1.845(2) . ?
Ni1 C1_3 1.902(3) . ?
Ni1 C1_2 1.903(3) . ?
C1_2 N1_2 1.353(4) . ?
C1_2 N2_2 1.357(4) . ?
N1_2 C3_2 1.389(4) . ?
N1_2 C13_2 1.445(4) . ?
C2_2 C3_2 1.343(5) . ?
C2_2 N2_2 1.389(4) . ?
C2_2 H2_2 0.9500 . ?
N2_2 C4_2 1.437(4) . ?
C3_2 H3_2 0.9500 . ?
C4_2 C5_2 1.393(4) . ?
C4_2 C9_2 1.399(4) . ?
C5_2 C6_2 1.390(5) . ?
C5_2 C10_2 1.501(5) . ?
C6_2 C7_2 1.395(5) . ?
C6_2 H6_2 0.9500 . ?
C7_2 C8_2 1.384(5) . ?
C7_2 C11_2 1.511(5) . ?
C8_2 C9_2 1.388(4) . ?
C8_2 H8_2 0.9500 . ?
C9_2 C12_2 1.506(4) . ?
C10_2 H10A_2 0.9800 . ?
C10_2 H10B_2 0.9800 . ?
C10_2 H10C_2 0.9800 . ?
C11_2 H11A_2 0.9800 . ?
C11_2 H11B_2 0.9800 . ?
C11_2 H11C_2 0.9800 . ?
C12_2 H12A_2 0.9800 . ?
C12_2 H12B_2 0.9800 . ?
C12_2 H12C_2 0.9800 . ?
C13_2 C14_2 1.390(4) . ?
C13_2 C18_2 1.398(4) . ?
C14_2 C15_2 1.393(5) . ?
C14_2 C19_2 1.508(4) . ?
C15_2 C16_2 1.394(4) . ?
C15_2 H15_2 0.9500 . ?
C16_2 C17_2 1.390(4) . ?
C16_2 C21_2 1.510(4) . ?
C17_2 C18_2 1.401(4) . ?
C17_2 H17_2 0.9500 . ?
C18_2 C20_2 1.502(4) . ?
C19_2 H19A_2 0.9800 . ?
C19_2 H19B_2 0.9800 . ?
C19_2 H19C_2 0.9800 . ?
C20_2 H20A_2 0.9800 . ?
C20_2 H20B_2 0.9800 . ?
C20_2 H20C_2 0.9800 . ?
C21_2 H21A_2 0.9800 . ?
C21_2 H21B_2 0.9800 . ?
C21_2 H21C_2 0.9800 . ?
C1_3 N1_3 1.355(4) . ?
C1_3 N2_3 1.355(4) . ?
N1_3 C2_3 1.391(4) . ?
N1_3 C13_3 1.446(4) . ?
C2_3 C3_3 1.337(5) . ?
C2_3 H2_3 0.9500 . ?
N2_3 C3_3 1.387(4) . ?
N2_3 C4_3 1.444(4) . ?
C3_3 H3_3 0.9500 . ?
C4_3 C5_3 1.397(4) . ?
C4_3 C9_3 1.398(4) . ?
C5_3 C6_3 1.394(4) . ?
C5_3 C10_3 1.513(4) . ?
C6_3 C7_3 1.390(4) . ?
C6_3 H6_3 0.9500 . ?
C7_3 C8_3 1.391(5) . ?
C7_3 C11_3 1.515(5) . ?
C8_3 C9_3 1.394(4) . ?
C8_3 H8_3 0.9500 . ?
C9_3 C12_3 1.506(4) . ?
C10_3 H10A_3 0.9800 . ?
C10_3 H10B_3 0.9800 . ?
C10_3 H10C_3 0.9800 . ?
C11_3 H11A_3 0.9800 . ?
C11_3 H11B_3 0.9800 . ?
C11_3 H11C_3 0.9800 . ?
C12_3 H12A_3 0.9800 . ?
C12_3 H12B_3 0.9800 . ?
C12_3 H12C_3 0.9800 . ?
C13_3 C18_3 1.392(4) . ?
C13_3 C14_3 1.392(4) . ?
C14_3 C15_3 1.394(4) . ?
C14_3 C19_3 1.509(4) . ?
C15_3 C16_3 1.395(5) . ?
C15_3 H15_3 0.9500 . ?
C16_3 C17_3 1.378(4) . ?
C16_3 C21_3 1.520(4) . ?
C17_3 C18_3 1.399(4) . ?
C17_3 H17_3 0.9500 . ?
C18_3 C20_3 1.506(4) . ?
C19_3 H19A_3 0.9800 . ?
C19_3 H19B_3 0.9800 . ?
C19_3 H19C_3 0.9800 . ?
C20_3 H20A_3 0.9800 . ?
C20_3 H20B_3 0.9800 . ?
C20_3 H20C_3 0.9800 . ?
C21_3 H21A_3 0.9800 . ?
C21_3 H21B_3 0.9800 . ?
C21_3 H21C_3 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
F1_1 Ni1 F2_1 179.77(9) . . ?
F1_1 Ni1 C1_3 90.16(10) . . ?
F2_1 Ni1 C1_3 90.03(10) . . ?
F1_1 Ni1 C1_2 90.48(10) . . ?
F2_1 Ni1 C1_2 89.32(10) . . ?
C1_3 Ni1 C1_2 178.49(12) . . ?
N1_2 C1_2 N2_2 104.3(3) . . ?
N1_2 C1_2 Ni1 128.2(2) . . ?
N2_2 C1_2 Ni1 127.4(2) . . ?
C1_2 N1_2 C3_2 111.2(3) . . ?
C1_2 N1_2 C13_2 124.0(3) . . ?
C3_2 N1_2 C13_2 124.7(3) . . ?
C3_2 C2_2 N2_2 106.7(3) . . ?
C3_2 C2_2 H2_2 126.7 . . ?
N2_2 C2_2 H2_2 126.7 . . ?
C1_2 N2_2 C2_2 111.1(3) . . ?
C1_2 N2_2 C4_2 124.4(2) . . ?
C2_2 N2_2 C4_2 124.4(2) . . ?
C2_2 C3_2 N1_2 106.7(3) . . ?
C2_2 C3_2 H3_2 126.6 . . ?
N1_2 C3_2 H3_2 126.6 . . ?
C5_2 C4_2 C9_2 122.3(3) . . ?
C5_2 C4_2 N2_2 119.4(3) . . ?
C9_2 C4_2 N2_2 118.2(3) . . ?
C6_2 C5_2 C4_2 117.7(3) . . ?
C6_2 C5_2 C10_2 121.6(3) . . ?
C4_2 C5_2 C10_2 120.8(3) . . ?
C5_2 C6_2 C7_2 121.5(3) . . ?
C5_2 C6_2 H6_2 119.3 . . ?
C7_2 C6_2 H6_2 119.3 . . ?
C8_2 C7_2 C6_2 118.9(3) . . ?
C8_2 C7_2 C11_2 119.7(3) . . ?
C6_2 C7_2 C11_2 121.5(3) . . ?
C7_2 C8_2 C9_2 121.7(3) . . ?
C7_2 C8_2 H8_2 119.2 . . ?
C9_2 C8_2 H8_2 119.2 . . ?
C8_2 C9_2 C4_2 117.7(3) . . ?
C8_2 C9_2 C12_2 121.0(3) . . ?
C4_2 C9_2 C12_2 121.3(3) . . ?
C5_2 C10_2 H10A_2 109.5 . . ?
C5_2 C10_2 H10B_2 109.5 . . ?
H10A_2 C10_2 H10B_2 109.5 . . ?
C5_2 C10_2 H10C_2 109.5 . . ?
H10A_2 C10_2 H10C_2 109.5 . . ?
H10B_2 C10_2 H10C_2 109.5 . . ?
C7_2 C11_2 H11A_2 109.5 . . ?
C7_2 C11_2 H11B_2 109.5 . . ?
H11A_2 C11_2 H11B_2 109.5 . . ?
C7_2 C11_2 H11C_2 109.5 . . ?
H11A_2 C11_2 H11C_2 109.5 . . ?
H11B_2 C11_2 H11C_2 109.5 . . ?
C9_2 C12_2 H12A_2 109.5 . . ?
C9_2 C12_2 H12B_2 109.5 . . ?
H12A_2 C12_2 H12B_2 109.5 . . ?
C9_2 C12_2 H12C_2 109.5 . . ?
H12A_2 C12_2 H12C_2 109.5 . . ?
H12B_2 C12_2 H12C_2 109.5 . . ?
C14_2 C13_2 C18_2 123.0(3) . . ?
C14_2 C13_2 N1_2 119.0(3) . . ?
C18_2 C13_2 N1_2 118.0(3) . . ?
C13_2 C14_2 C15_2 117.9(3) . . ?
C13_2 C14_2 C19_2 120.8(3) . . ?
C15_2 C14_2 C19_2 121.3(3) . . ?
C14_2 C15_2 C16_2 121.6(3) . . ?
C14_2 C15_2 H15_2 119.2 . . ?
C16_2 C15_2 H15_2 119.2 . . ?
C17_2 C16_2 C15_2 118.4(3) . . ?
C17_2 C16_2 C21_2 120.4(3) . . ?
C15_2 C16_2 C21_2 121.2(3) . . ?
C16_2 C17_2 C18_2 122.3(3) . . ?
C16_2 C17_2 H17_2 118.8 . . ?
C18_2 C17_2 H17_2 118.8 . . ?
C13_2 C18_2 C17_2 116.7(3) . . ?
C13_2 C18_2 C20_2 121.8(3) . . ?
C17_2 C18_2 C20_2 121.5(3) . . ?
C14_2 C19_2 H19A_2 109.5 . . ?
C14_2 C19_2 H19B_2 109.5 . . ?
H19A_2 C19_2 H19B_2 109.5 . . ?
C14_2 C19_2 H19C_2 109.5 . . ?
H19A_2 C19_2 H19C_2 109.5 . . ?
H19B_2 C19_2 H19C_2 109.5 . . ?
C18_2 C20_2 H20A_2 109.5 . . ?
C18_2 C20_2 H20B_2 109.5 . . ?
H20A_2 C20_2 H20B_2 109.5 . . ?
C18_2 C20_2 H20C_2 109.5 . . ?
H20A_2 C20_2 H20C_2 109.5 . . ?
H20B_2 C20_2 H20C_2 109.5 . . ?
C16_2 C21_2 H21A_2 109.5 . . ?
C16_2 C21_2 H21B_2 109.5 . . ?
H21A_2 C21_2 H21B_2 109.5 . . ?
C16_2 C21_2 H21C_2 109.5 . . ?
H21A_2 C21_2 H21C_2 109.5 . . ?
H21B_2 C21_2 H21C_2 109.5 . . ?
N1_3 C1_3 N2_3 104.0(2) . . ?
N1_3 C1_3 Ni1 126.9(2) . . ?
N2_3 C1_3 Ni1 129.1(2) . . ?
C1_3 N1_3 C2_3 111.1(2) . . ?
C1_3 N1_3 C13_3 125.5(2) . . ?
C2_3 N1_3 C13_3 123.0(2) . . ?
C3_3 C2_3 N1_3 106.9(3) . . ?
C3_3 C2_3 H2_3 126.5 . . ?
N1_3 C2_3 H2_3 126.5 . . ?
C1_3 N2_3 C3_3 111.6(3) . . ?
C1_3 N2_3 C4_3 124.1(2) . . ?
C3_3 N2_3 C4_3 124.2(3) . . ?
C2_3 C3_3 N2_3 106.5(3) . . ?
C2_3 C3_3 H3_3 126.8 . . ?
N2_3 C3_3 H3_3 126.8 . . ?
C5_3 C4_3 C9_3 122.5(3) . . ?
C5_3 C4_3 N2_3 119.1(3) . . ?
C9_3 C4_3 N2_3 118.4(3) . . ?
C6_3 C5_3 C4_3 117.5(3) . . ?
C6_3 C5_3 C10_3 121.1(3) . . ?
C4_3 C5_3 C10_3 121.3(3) . . ?
C7_3 C6_3 C5_3 122.0(3) . . ?
C7_3 C6_3 H6_3 119.0 . . ?
C5_3 C6_3 H6_3 119.0 . . ?
C6_3 C7_3 C8_3 118.5(3) . . ?
C6_3 C7_3 C11_3 121.6(3) . . ?
C8_3 C7_3 C11_3 119.9(3) . . ?
C7_3 C8_3 C9_3 122.0(3) . . ?
C7_3 C8_3 H8_3 119.0 . . ?
C9_3 C8_3 H8_3 119.0 . . ?
C8_3 C9_3 C4_3 117.5(3) . . ?
C8_3 C9_3 C12_3 121.8(3) . . ?
C4_3 C9_3 C12_3 120.7(3) . . ?
C5_3 C10_3 H10A_3 109.5 . . ?
C5_3 C10_3 H10B_3 109.5 . . ?
H10A_3 C10_3 H10B_3 109.5 . . ?
C5_3 C10_3 H10C_3 109.5 . . ?
H10A_3 C10_3 H10C_3 109.5 . . ?
H10B_3 C10_3 H10C_3 109.5 . . ?
C7_3 C11_3 H11A_3 109.5 . . ?
C7_3 C11_3 H11B_3 109.5 . . ?
H11A_3 C11_3 H11B_3 109.5 . . ?
C7_3 C11_3 H11C_3 109.5 . . ?
H11A_3 C11_3 H11C_3 109.5 . . ?
H11B_3 C11_3 H11C_3 109.5 . . ?
C9_3 C12_3 H12A_3 109.5 . . ?
C9_3 C12_3 H12B_3 109.5 . . ?
H12A_3 C12_3 H12B_3 109.5 . . ?
C9_3 C12_3 H12C_3 109.5 . . ?
H12A_3 C12_3 H12C_3 109.5 . . ?
H12B_3 C12_3 H12C_3 109.5 . . ?
C18_3 C13_3 C14_3 123.0(3) . . ?
C18_3 C13_3 N1_3 117.6(3) . . ?
C14_3 C13_3 N1_3 119.3(3) . . ?
C13_3 C14_3 C15_3 117.9(3) . . ?
C13_3 C14_3 C19_3 121.0(3) . . ?
C15_3 C14_3 C19_3 121.1(3) . . ?
C14_3 C15_3 C16_3 120.7(3) . . ?
C14_3 C15_3 H15_3 119.6 . . ?
C16_3 C15_3 H15_3 119.6 . . ?
C17_3 C16_3 C15_3 119.5(3) . . ?
C17_3 C16_3 C21_3 120.7(3) . . ?
C15_3 C16_3 C21_3 119.8(3) . . ?
C16_3 C17_3 C18_3 121.8(3) . . ?
C16_3 C17_3 H17_3 119.1 . . ?
C18_3 C17_3 H17_3 119.1 . . ?
C13_3 C18_3 C17_3 117.0(3) . . ?
C13_3 C18_3 C20_3 121.7(3) . . ?
C17_3 C18_3 C20_3 121.2(3) . . ?
C14_3 C19_3 H19A_3 109.5 . . ?
C14_3 C19_3 H19B_3 109.5 . . ?
H19A_3 C19_3 H19B_3 109.5 . . ?
C14_3 C19_3 H19C_3 109.5 . . ?
H19A_3 C19_3 H19C_3 109.5 . . ?
H19B_3 C19_3 H19C_3 109.5 . . ?
C18_3 C20_3 H20A_3 109.5 . . ?
C18_3 C20_3 H20B_3 109.5 . . ?
H20A_3 C20_3 H20B_3 109.5 . . ?
C18_3 C20_3 H20C_3 109.5 . . ?
H20A_3 C20_3 H20C_3 109.5 . . ?
H20B_3 C20_3 H20C_3 109.5 . . ?
C16_3 C21_3 H21A_3 109.5 . . ?
C16_3 C21_3 H21B_3 109.5 . . ?
H21A_3 C21_3 H21B_3 109.5 . . ?
C16_3 C21_3 H21C_3 109.5 . . ?
H21A_3 C21_3 H21C_3 109.5 . . ?
H21B_3 C21_3 H21C_3 109.5 . . ?

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
N2_2 C1_2 N1_2 C3_2 0.1(3) . . . . ?
Ni1 C1_2 N1_2 C3_2 -177.4(2) . . . . ?
N2_2 C1_2 N1_2 C13_2 -177.4(3) . . . . ?
Ni1 C1_2 N1_2 C13_2 5.1(4) . . . . ?
N1_2 C1_2 N2_2 C2_2 0.1(3) . . . . ?
Ni1 C1_2 N2_2 C2_2 177.6(2) . . . . ?
N1_2 C1_2 N2_2 C4_2 -175.5(3) . . . . ?
Ni1 C1_2 N2_2 C4_2 2.0(4) . . . . ?
C3_2 C2_2 N2_2 C1_2 -0.2(4) . . . . ?
C3_2 C2_2 N2_2 C4_2 175.3(3) . . . . ?
N2_2 C2_2 C3_2 N1_2 0.3(4) . . . . ?
C1_2 N1_2 C3_2 C2_2 -0.2(4) . . . . ?
C13_2 N1_2 C3_2 C2_2 177.2(3) . . . . ?
C1_2 N2_2 C4_2 C5_2 -102.5(3) . . . . ?
C2_2 N2_2 C4_2 C5_2 82.5(4) . . . . ?
C1_2 N2_2 C4_2 C9_2 77.6(4) . . . . ?
C2_2 N2_2 C4_2 C9_2 -97.4(3) . . . . ?
C9_2 C4_2 C5_2 C6_2 1.9(5) . . . . ?
N2_2 C4_2 C5_2 C6_2 -178.0(3) . . . . ?
C9_2 C4_2 C5_2 C10_2 -176.8(3) . . . . ?
N2_2 C4_2 C5_2 C10_2 3.2(4) . . . . ?
C4_2 C5_2 C6_2 C7_2 2.9(5) . . . . ?
C10_2 C5_2 C6_2 C7_2 -178.4(3) . . . . ?
C5_2 C6_2 C7_2 C8_2 -4.8(5) . . . . ?
C5_2 C6_2 C7_2 C11_2 174.8(3) . . . . ?
C6_2 C7_2 C8_2 C9_2 1.9(5) . . . . ?
C11_2 C7_2 C8_2 C9_2 -177.6(3) . . . . ?
C7_2 C8_2 C9_2 C4_2 2.6(5) . . . . ?
C7_2 C8_2 C9_2 C12_2 -175.6(3) . . . . ?
C5_2 C4_2 C9_2 C8_2 -4.6(4) . . . . ?
N2_2 C4_2 C9_2 C8_2 175.4(3) . . . . ?
C5_2 C4_2 C9_2 C12_2 173.6(3) . . . . ?
N2_2 C4_2 C9_2 C12_2 -6.4(4) . . . . ?
C1_2 N1_2 C13_2 C14_2 -105.8(3) . . . . ?
C3_2 N1_2 C13_2 C14_2 77.1(4) . . . . ?
C1_2 N1_2 C13_2 C18_2 74.2(4) . . . . ?
C3_2 N1_2 C13_2 C18_2 -103.0(4) . . . . ?
C18_2 C13_2 C14_2 C15_2 1.2(5) . . . . ?
N1_2 C13_2 C14_2 C15_2 -178.8(3) . . . . ?
C18_2 C13_2 C14_2 C19_2 -176.6(3) . . . . ?
N1_2 C13_2 C14_2 C19_2 3.4(4) . . . . ?
C13_2 C14_2 C15_2 C16_2 0.3(5) . . . . ?
C19_2 C14_2 C15_2 C16_2 178.1(3) . . . . ?
C14_2 C15_2 C16_2 C17_2 -0.3(5) . . . . ?
C14_2 C15_2 C16_2 C21_2 -179.1(3) . . . . ?
C15_2 C16_2 C17_2 C18_2 -1.2(5) . . . . ?
C21_2 C16_2 C17_2 C18_2 177.7(3) . . . . ?
C14_2 C13_2 C18_2 C17_2 -2.6(4) . . . . ?
N1_2 C13_2 C18_2 C17_2 177.5(3) . . . . ?
C14_2 C13_2 C18_2 C20_2 175.8(3) . . . . ?
N1_2 C13_2 C18_2 C20_2 -4.1(4) . . . . ?
C16_2 C17_2 C18_2 C13_2 2.5(4) . . . . ?
C16_2 C17_2 C18_2 C20_2 -175.9(3) . . . . ?
N2_3 C1_3 N1_3 C2_3 0.2(3) . . . . ?
Ni1 C1_3 N1_3 C2_3 179.2(2) . . . . ?
N2_3 C1_3 N1_3 C13_3 -172.7(2) . . . . ?
Ni1 C1_3 N1_3 C13_3 6.3(4) . . . . ?
C1_3 N1_3 C2_3 C3_3 -0.3(3) . . . . ?
C13_3 N1_3 C2_3 C3_3 172.9(3) . . . . ?
N1_3 C1_3 N2_3 C3_3 -0.1(3) . . . . ?
Ni1 C1_3 N2_3 C3_3 -179.1(2) . . . . ?
N1_3 C1_3 N2_3 C4_3 176.8(2) . . . . ?
Ni1 C1_3 N2_3 C4_3 -2.2(4) . . . . ?
N1_3 C2_3 C3_3 N2_3 0.2(3) . . . . ?
C1_3 N2_3 C3_3 C2_3 -0.1(3) . . . . ?
C4_3 N2_3 C3_3 C2_3 -176.9(3) . . . . ?
C1_3 N2_3 C4_3 C5_3 78.0(4) . . . . ?
C3_3 N2_3 C4_3 C5_3 -105.6(3) . . . . ?
C1_3 N2_3 C4_3 C9_3 -101.3(3) . . . . ?
C3_3 N2_3 C4_3 C9_3 75.1(4) . . . . ?
C9_3 C4_3 C5_3 C6_3 -0.7(4) . . . . ?
N2_3 C4_3 C5_3 C6_3 -180.0(3) . . . . ?
C9_3 C4_3 C5_3 C10_3 178.9(3) . . . . ?
N2_3 C4_3 C5_3 C10_3 -0.3(4) . . . . ?
C4_3 C5_3 C6_3 C7_3 1.0(5) . . . . ?
C10_3 C5_3 C6_3 C7_3 -178.6(3) . . . . ?
C5_3 C6_3 C7_3 C8_3 -0.7(5) . . . . ?
C5_3 C6_3 C7_3 C11_3 177.3(3) . . . . ?
C6_3 C7_3 C8_3 C9_3 0.0(5) . . . . ?
C11_3 C7_3 C8_3 C9_3 -178.0(3) . . . . ?
C7_3 C8_3 C9_3 C4_3 0.2(5) . . . . ?
C7_3 C8_3 C9_3 C12_3 179.0(3) . . . . ?
C5_3 C4_3 C9_3 C8_3 0.1(4) . . . . ?
N2_3 C4_3 C9_3 C8_3 179.4(3) . . . . ?
C5_3 C4_3 C9_3 C12_3 -178.7(3) . . . . ?
N2_3 C4_3 C9_3 C12_3 0.6(4) . . . . ?
C1_3 N1_3 C13_3 C18_3 79.3(4) . . . . ?
C2_3 N1_3 C13_3 C18_3 -92.9(3) . . . . ?
C1_3 N1_3 C13_3 C14_3 -104.1(3) . . . . ?
C2_3 N1_3 C13_3 C14_3 83.8(4) . . . . ?
C18_3 C13_3 C14_3 C15_3 2.7(4) . . . . ?
N1_3 C13_3 C14_3 C15_3 -173.8(3) . . . . ?
C18_3 C13_3 C14_3 C19_3 -175.0(3) . . . . ?
N1_3 C13_3 C14_3 C19_3 8.5(4) . . . . ?
C13_3 C14_3 C15_3 C16_3 -1.2(5) . . . . ?
C19_3 C14_3 C15_3 C16_3 176.5(3) . . . . ?
C14_3 C15_3 C16_3 C17_3 -0.2(5) . . . . ?
C14_3 C15_3 C16_3 C21_3 179.5(3) . . . . ?
C15_3 C16_3 C17_3 C18_3 0.4(5) . . . . ?
C21_3 C16_3 C17_3 C18_3 -179.3(3) . . . . ?
C14_3 C13_3 C18_3 C17_3 -2.5(4) . . . . ?
N1_3 C13_3 C18_3 C17_3 174.0(3) . . . . ?
C14_3 C13_3 C18_3 C20_3 177.4(3) . . . . ?
N1_3 C13_3 C18_3 C20_3 -6.1(4) . . . . ?
C16_3 C17_3 C18_3 C13_3 0.9(4) . . . . ?
C16_3 C17_3 C18_3 C20_3 -179.0(3) . . . . ?

_refine_diff_density_max         0.729
_refine_diff_density_min         -0.921
_refine_diff_density_rms         0.126

