# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
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data_2_a
_database_code_depnum_ccdc_archive 'CCDC 2166722'
loop_
_audit_author_name
_audit_author_address
'Liviu Mirica'
;University of Illinois at Urbana Champaign
United States of America
;
_audit_update_record             
;
2022-04-16 deposited with the CCDC.	2022-06-09 downloaded from the CCDC.
;
_audit_creation_date             2022-04-14
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelxl_version_number           2014/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(B F4), C19 H39 N5 Ni, C2 H3 N'
_chemical_formula_sum            'C21 H42 B2 F8 N6 Ni'
_chemical_formula_weight         610.93
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.9809(3)
_cell_length_b                   10.6534(4)
_cell_length_c                   14.0509(5)
_cell_angle_alpha                86.114(2)
_cell_angle_beta                 75.996(2)
_cell_angle_gamma                81.687(2)
_cell_volume                     1433.57(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    17484
_cell_measurement_temperature    100.15
_cell_measurement_theta_max      28.291
_cell_measurement_theta_min      2.403
_shelx_estimated_absorpt_T_max   0.926
_shelx_estimated_absorpt_T_min   0.638
_exptl_absorpt_coefficient_mu    0.751
_exptl_absorpt_correction_T_max  0.9751
_exptl_absorpt_correction_T_min  0.6793
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2014/4 (Bruker,2014/4) was used for absorption correction. wR2(int) was 0.0545 before and 0.0445 after correction. The Ratio of minimum to maximum transmission is 0.6966. The λ/2 correction factor is 0.00150.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            blue/purple
_exptl_crystal_density_diffrn    1.415
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Plate
_exptl_crystal_F_000             640
_exptl_crystal_preparation       ?
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Acetonitrile, Diethylether'
_exptl_crystal_size_max          0.657
_exptl_crystal_size_mid          0.372
_exptl_crystal_size_min          0.104
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0329
_diffrn_reflns_av_unetI/netI     0.0233
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            35173
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.306
_diffrn_reflns_theta_min         2.290
_diffrn_ambient_temperature      100.15
_diffrn_detector                 'Bruker D8 Venture'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            'CPAD area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'kappa diffractometer'
_diffrn_measurement_device_type  'Bruker Kappa/ApexII CCD'
_diffrn_measurement_method       'profile data from φ and ω scans'
_diffrn_radiation_monochromator  multi-mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_target            Mo
_diffrn_source_type              'Ius microfocus sealed tube'
_diffrn_special_details          ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                6553
_reflns_number_total             7125
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.577
_refine_diff_density_min         -0.403
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     352
_refine_ls_number_reflns         7125
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0301
_refine_ls_R_factor_gt           0.0268
_refine_ls_restrained_S_all      1.057
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0304P)²+0.6348P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0658
_refine_ls_wR_factor_ref         0.0678
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7), C10(H10), C13(H13)
2.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C5(H5A,H5B), C6(H6A,H6B)
2.c Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C9(H9A,H9B,H9C), C11(H11A,H11B,H11C), C12(H12A,H12B,H12C),
 C14(H14A,H14B,H14C), C15(H15A,H15B,H15C), C17(H17A,H17B,H17C), C19(H19A,H19B,
 H19C), C21(H21A,H21B,H21C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
B1 B 0.51475(16) 0.28942(15) 0.84000(11) 0.0215(3) Uani 1 1 d . . . . .
F1 F 0.60685(12) 0.29745(12) 0.89718(7) 0.0489(3) Uani 1 1 d . . . . .
F2 F 0.38178(11) 0.28475(13) 0.89668(8) 0.0526(3) Uani 1 1 d . . . . .
F3 F 0.55589(11) 0.18149(8) 0.78409(8) 0.0381(2) Uani 1 1 d . . . . .
F4 F 0.51378(10) 0.39455(7) 0.77496(6) 0.02687(18) Uani 1 1 d . . . . .
B2 B 0.13957(16) 0.27052(15) 0.46187(11) 0.0214(3) Uani 1 1 d . . . . .
F5 F 0.13702(9) 0.26776(9) 0.36341(6) 0.0317(2) Uani 1 1 d . . . . .
F6 F 0.20775(12) 0.36962(10) 0.47577(7) 0.0409(2) Uani 1 1 d . . . . .
F7 F 0.21285(13) 0.15869(10) 0.48889(9) 0.0488(3) Uani 1 1 d . . . . .
F8 F 0.00514(11) 0.28439(13) 0.51735(8) 0.0523(3) Uani 1 1 d . . . . .
C1 C 0.45099(12) 0.65419(11) 0.65107(8) 0.0117(2) Uani 1 1 d . . . . .
H1A H 0.5127 0.6373 0.5853 0.014 Uiso 1 1 calc R . . . .
H1B H 0.4406 0.5717 0.6871 0.014 Uiso 1 1 calc R . . . .
C2 C 0.51825(12) 0.73609(11) 0.70612(8) 0.0125(2) Uani 1 1 d . . . . .
H2A H 0.6010 0.6853 0.7230 0.015 Uiso 1 1 calc R . . . .
H2B H 0.5501 0.8085 0.6628 0.015 Uiso 1 1 calc R . . . .
C3 C 0.38912(12) 0.68021(11) 0.87281(8) 0.0131(2) Uani 1 1 d . . . . .
H3A H 0.4381 0.6865 0.9254 0.016 Uiso 1 1 calc R . . . .
H3B H 0.4247 0.5975 0.8417 0.016 Uiso 1 1 calc R . . . .
C4 C 0.23321(12) 0.68556(11) 0.91782(8) 0.0135(2) Uani 1 1 d . . . . .
H4A H 0.2143 0.6045 0.9539 0.016 Uiso 1 1 calc R . . . .
H4B H 0.2029 0.7546 0.9652 0.016 Uiso 1 1 calc R . . . .
C5 C 0.17650(12) 0.59400(11) 0.77900(8) 0.0127(2) Uani 1 1 d . . . . .
H5A H 0.0940 0.5482 0.7981 0.015 Uiso 1 1 calc R . . . .
H5B H 0.2576 0.5361 0.7920 0.015 Uiso 1 1 calc R . . . .
C6 C 0.20309(12) 0.62891(11) 0.66981(8) 0.0122(2) Uani 1 1 d . . . . .
H6A H 0.2342 0.5507 0.6319 0.015 Uiso 1 1 calc R . . . .
H6B H 0.1151 0.6700 0.6542 0.015 Uiso 1 1 calc R . . . .
C7 C 0.31324(12) 0.76600(11) 0.53577(8) 0.0126(2) Uani 1 1 d . . . . .
H7 H 0.2181 0.8110 0.5358 0.015 Uiso 1 1 calc R . . . .
C8 C 0.34384(14) 0.66008(12) 0.46223(9) 0.0169(2) Uani 1 1 d . . . . .
H8A H 0.4341 0.6103 0.4633 0.025 Uiso 1 1 calc GR . . . .
H8B H 0.3464 0.6974 0.3962 0.025 Uiso 1 1 calc GR . . . .
H8C H 0.2706 0.6047 0.4801 0.025 Uiso 1 1 calc GR . . . .
C9 C 0.41492(13) 0.86281(11) 0.50301(8) 0.0154(2) Uani 1 1 d . . . . .
H9A H 0.3890 0.9333 0.5481 0.023 Uiso 1 1 calc GR . . . .
H9B H 0.4118 0.8951 0.4365 0.023 Uiso 1 1 calc GR . . . .
H9C H 0.5094 0.8223 0.5034 0.023 Uiso 1 1 calc GR . . . .
C10 C 0.47902(12) 0.88969(11) 0.83508(8) 0.0138(2) Uani 1 1 d . . . . .
H10 H 0.4928 0.9566 0.7814 0.017 Uiso 1 1 calc R . . . .
C11 C 0.62078(13) 0.84841(13) 0.85911(10) 0.0201(3) Uani 1 1 d . . . . .
H11A H 0.6108 0.7859 0.9140 0.030 Uiso 1 1 calc GR . . . .
H11B H 0.6559 0.9225 0.8772 0.030 Uiso 1 1 calc GR . . . .
H11C H 0.6865 0.8103 0.8015 0.030 Uiso 1 1 calc GR . . . .
C12 C 0.37442(14) 0.95088(12) 0.92246(9) 0.0177(2) Uani 1 1 d . . . . .
H12A H 0.2833 0.9719 0.9066 0.027 Uiso 1 1 calc GR . . . .
H12B H 0.4058 1.0286 0.9377 0.027 Uiso 1 1 calc GR . . . .
H12C H 0.3668 0.8916 0.9794 0.027 Uiso 1 1 calc GR . . . .
C13 C -0.00116(12) 0.74746(12) 0.88214(9) 0.0151(2) Uani 1 1 d . . . . .
H13 H -0.0481 0.7568 0.8263 0.018 Uiso 1 1 calc R . . . .
C14 C -0.02605(13) 0.87649(12) 0.92910(9) 0.0193(2) Uani 1 1 d . . . . .
H14A H -0.0021 0.8663 0.9931 0.029 Uiso 1 1 calc GR . . . .
H14B H -0.1244 0.9118 0.9379 0.029 Uiso 1 1 calc GR . . . .
H14C H 0.0323 0.9342 0.8865 0.029 Uiso 1 1 calc GR . . . .
C15 C -0.07078(14) 0.65131(13) 0.95622(10) 0.0220(3) Uani 1 1 d . . . . .
H15A H -0.0312 0.6442 1.0140 0.033 Uiso 1 1 calc GR . . . .
H15B H -0.0548 0.5684 0.9262 0.033 Uiso 1 1 calc GR . . . .
H15C H -0.1711 0.6795 0.9760 0.033 Uiso 1 1 calc GR . . . .
C16 C -0.02774(13) 0.97783(12) 0.67712(9) 0.0161(2) Uani 1 1 d . . . . .
C17 C -0.14580(15) 1.05273(14) 0.64798(12) 0.0264(3) Uani 1 1 d . . . . .
H17A H -0.1842 1.0015 0.6084 0.040 Uiso 1 1 calc GR . . . .
H17B H -0.1153 1.1279 0.6093 0.040 Uiso 1 1 calc GR . . . .
H17C H -0.2175 1.0794 0.7066 0.040 Uiso 1 1 calc GR . . . .
C18 C 0.28763(12) 1.13499(12) 0.70185(9) 0.0150(2) Uani 1 1 d . . . . .
C19 C 0.28357(15) 1.27180(12) 0.69038(10) 0.0209(3) Uani 1 1 d . . . . .
H19A H 0.2390 1.3029 0.6368 0.031 Uiso 1 1 calc GR . . . .
H19B H 0.3787 1.2936 0.6751 0.031 Uiso 1 1 calc GR . . . .
H19C H 0.2302 1.3113 0.7515 0.031 Uiso 1 1 calc GR . . . .
N1 N 0.31093(10) 0.71670(9) 0.63972(7) 0.01007(18) Uani 1 1 d . . . . .
N2 N 0.42033(10) 0.78525(9) 0.79765(7) 0.01076(18) Uani 1 1 d . . . . .
N3 N 0.15245(10) 0.70827(9) 0.84022(7) 0.01140(18) Uani 1 1 d . . . . .
N4 N 0.06473(11) 0.91941(10) 0.69974(8) 0.0149(2) Uani 1 1 d . . . . .
N5 N 0.29116(11) 1.02800(10) 0.71069(7) 0.0151(2) Uani 1 1 d . . . . .
Ni1 Ni 0.24141(2) 0.84870(2) 0.74701(2) 0.00917(5) Uani 1 1 d . . . . .
C20 C 0.91346(16) 0.33061(18) 0.77892(12) 0.0338(4) Uani 1 1 d . . . . .
C21 C 0.85094(19) 0.43417(17) 0.72398(14) 0.0381(4) Uani 1 1 d . . . . .
H21A H 0.8983 0.4296 0.6543 0.057 Uiso 1 1 calc GR . . . .
H21B H 0.8604 0.5155 0.7487 0.057 Uiso 1 1 calc GR . . . .
H21C H 0.7520 0.4271 0.7320 0.057 Uiso 1 1 calc GR . . . .
N6 N 0.96430(17) 0.24951(19) 0.82075(12) 0.0502(4) 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
B1 F1 1.3739(18) . ?
B1 F2 1.3785(18) . ?
B1 F3 1.3920(18) . ?
B1 F4 1.3971(16) . ?
B2 F5 1.3923(18) . ?
B2 F6 1.3841(17) . ?
B2 F7 1.3855(18) . ?
B2 F8 1.3718(18) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C1 C2 1.5239(15) . ?
C1 N1 1.4991(14) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 N2 1.4893(14) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.5256(16) . ?
C3 N2 1.4987(14) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 N3 1.4934(14) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C6 1.5220(15) . ?
C5 N3 1.4957(14) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 N1 1.4931(14) . ?
C7 H7 1.0000 . ?
C7 C8 1.5298(16) . ?
C7 C9 1.5224(16) . ?
C7 N1 1.5142(14) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10 1.0000 . ?
C10 C11 1.5299(17) . ?
C10 C12 1.5211(17) . ?
C10 N2 1.5081(14) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13 1.0000 . ?
C13 C14 1.5270(17) . ?
C13 C15 1.5254(17) . ?
C13 N3 1.5109(15) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 C17 1.4526(17) . ?
C16 N4 1.1355(16) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 C19 1.4513(17) . ?
C18 N5 1.1345(16) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
N1 Ni1 2.0568(9) . ?
N2 Ni1 2.0864(10) . ?
N3 Ni1 2.0730(10) . ?
N4 Ni1 2.0574(10) . ?
N5 Ni1 2.0434(10) . ?
C20 C21 1.456(2) . ?
C20 N6 1.139(2) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 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 B1 F2 111.24(12) . . ?
F1 B1 F3 110.25(13) . . ?
F1 B1 F4 109.74(13) . . ?
F2 B1 F3 108.97(13) . . ?
F2 B1 F4 109.11(12) . . ?
F3 B1 F4 107.45(11) . . ?
F6 B2 F5 109.83(12) . . ?
F6 B2 F7 107.70(12) . . ?
F7 B2 F5 109.50(12) . . ?
F8 B2 F5 108.77(12) . . ?
F8 B2 F6 110.74(13) . . ?
F8 B2 F7 110.29(13) . . ?
H1A C1 H1B 107.9 . . ?
C2 C1 H1A 109.2 . . ?
C2 C1 H1B 109.2 . . ?
N1 C1 H1A 109.2 . . ?
N1 C1 H1B 109.2 . . ?
N1 C1 C2 111.97(9) . . ?
C1 C2 H2A 109.2 . . ?
C1 C2 H2B 109.2 . . ?
H2A C2 H2B 107.9 . . ?
N2 C2 C1 112.07(9) . . ?
N2 C2 H2A 109.2 . . ?
N2 C2 H2B 109.2 . . ?
H3A C3 H3B 107.9 . . ?
C4 C3 H3A 109.3 . . ?
C4 C3 H3B 109.3 . . ?
N2 C3 H3A 109.3 . . ?
N2 C3 H3B 109.3 . . ?
N2 C3 C4 111.79(9) . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 108.1 . . ?
N3 C4 C3 110.85(9) . . ?
N3 C4 H4A 109.5 . . ?
N3 C4 H4B 109.5 . . ?
H5A C5 H5B 107.9 . . ?
C6 C5 H5A 109.2 . . ?
C6 C5 H5B 109.2 . . ?
N3 C5 H5A 109.2 . . ?
N3 C5 H5B 109.2 . . ?
N3 C5 C6 112.12(9) . . ?
C5 C6 H6A 109.3 . . ?
C5 C6 H6B 109.3 . . ?
H6A C6 H6B 107.9 . . ?
N1 C6 C5 111.73(9) . . ?
N1 C6 H6A 109.3 . . ?
N1 C6 H6B 109.3 . . ?
C8 C7 H7 107.2 . . ?
C9 C7 H7 107.2 . . ?
C9 C7 C8 110.70(10) . . ?
N1 C7 H7 107.2 . . ?
N1 C7 C8 112.98(9) . . ?
N1 C7 C9 111.32(9) . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C7 C9 H9A 109.5 . . ?
C7 C9 H9B 109.5 . . ?
C7 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C11 C10 H10 106.9 . . ?
C12 C10 H10 106.9 . . ?
C12 C10 C11 111.06(10) . . ?
N2 C10 H10 106.9 . . ?
N2 C10 C11 114.18(10) . . ?
N2 C10 C12 110.51(10) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C14 C13 H13 107.5 . . ?
C15 C13 H13 107.5 . . ?
C15 C13 C14 109.36(10) . . ?
N3 C13 H13 107.5 . . ?
N3 C13 C14 110.74(10) . . ?
N3 C13 C15 114.05(10) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N4 C16 C17 179.85(17) . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
N5 C18 C19 179.82(18) . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C1 N1 C7 112.49(9) . . ?
C1 N1 Ni1 106.68(6) . . ?
C6 N1 C1 111.70(9) . . ?
C6 N1 C7 108.78(8) . . ?
C6 N1 Ni1 100.79(7) . . ?
C7 N1 Ni1 115.88(7) . . ?
C2 N2 C3 111.12(9) . . ?
C2 N2 C10 109.44(9) . . ?
C2 N2 Ni1 101.13(6) . . ?
C3 N2 C10 112.56(9) . . ?
C3 N2 Ni1 108.52(7) . . ?
C10 N2 Ni1 113.52(7) . . ?
C4 N3 C5 110.45(9) . . ?
C4 N3 C13 112.43(9) . . ?
C4 N3 Ni1 105.36(7) . . ?
C5 N3 C13 111.22(9) . . ?
C5 N3 Ni1 105.45(7) . . ?
C13 N3 Ni1 111.56(7) . . ?
C16 N4 Ni1 168.35(10) . . ?
C18 N5 Ni1 164.07(10) . . ?
N1 Ni1 N2 87.92(4) . . ?
N1 Ni1 N3 88.45(4) . . ?
N1 Ni1 N4 94.46(4) . . ?
N3 Ni1 N2 85.51(4) . . ?
N4 Ni1 N2 177.32(4) . . ?
N4 Ni1 N3 95.77(4) . . ?
N5 Ni1 N1 116.80(4) . . ?
N5 Ni1 N2 94.61(4) . . ?
N5 Ni1 N3 154.75(4) . . ?
N5 Ni1 N4 83.23(4) . . ?
N6 C20 C21 178.90(19) . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?

_olex2_exptl_crystal_mounting_method 'mounted with a spindle axis of (4 1 6)'
_olex2_submission_special_instructions 'No special instructions were received'
_chemical_properties_physical    Moisture-sensitive
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_dd62ys
_database_code_depnum_ccdc_archive 'CCDC 2166723'
loop_
_audit_author_name
_audit_author_address
'Liviu Mirica'
;University of Illinois at Urbana Champaign
United States of America
;
_audit_update_record             
;
2022-04-16 deposited with the CCDC.	2022-06-09 downloaded from the CCDC.
;
_audit_creation_date             2022-04-14
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelxl_version_number           2014/6

_audit_contact_author            
;
Danielle L. Gray 
University of Illinois 
School of Chemical Sciences, Box 59-1 
505 South Mathews Avenue 
Urbana, Illinois  61801 
USA 
;
_audit_contact_letter            
;
Please consider this CIF submission for publication as a structural paper 
in Acta Crystallographica E. 
;
_chemical_name_common            ?
_chemical_name_systematic        
;
? 
;
_chemical_formula_moiety         '1(C30 H60 N6 Ni1), 2(F6 P1)'
_chemical_formula_sum            'C30 H60 F12 N6 Ni P2'
_chemical_formula_weight         853.49
_chemical_absolute_configuration ?
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      hexagonal
_space_group_IT_number           173
_space_group_name_H-M_alt        'P 63'
_space_group_name_Hall           'P 6c'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'-x, -y, z+1/2'
'y, -x+y, z+1/2'
'x-y, x, z+1/2'

_cell_length_a                   11.1194(2)
_cell_length_b                   11.1194(2)
_cell_length_c                   18.1833(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     1947.00(8)
_cell_formula_units_Z            1.99998
_cell_measurement_reflns_used    27422
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.10
_cell_measurement_theta_min      2.39
_shelx_estimated_absorpt_T_max   0.849
_shelx_estimated_absorpt_T_min   0.666
_exptl_absorpt_coefficient_mu    0.669
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6821
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   'SADABS V2016/2 (Krause et al., 2015)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            green
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.456
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             896
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1.00 -1.00 0.00 0.0890
2.00 3.00 1.00 0.1560
-1.00 -2.00 4.00 0.1850
-1.00 4.00 2.00 0.1270
1.00 -3.00 1.00 0.0940
-5.00 2.00 2.00 0.1140
-5.00 2.00 0.00 0.1400
-3.00 0.00 4.00 0.1590
-4.00 3.00 -5.00 0.2600
-3.00 0.00 1.00 0.0930
1.00 0.00 0.00 0.1080
0.00 -1.00 0.00 0.0790
1.00 -3.00 -5.00 0.2480
-1.00 1.00 5.00 0.2680
1.00 1.00 -6.00 0.2570
-4.00 6.00 3.00 0.1280
6.00 -6.00 -1.00 0.0990
5.00 -4.00 0.00 0.1110

_exptl_crystal_id                ed62ys
_exptl_crystal_preparation       
;
The data crystal was mounted using oil (Paratone-N, Exxon) to a 
0.3 mm cryo-loop (Hampton Research) with the (-1 -1 5) scattering 
planes roughly normal to the spindle axis. 
;
_exptl_crystal_size_max          0.661
_exptl_crystal_size_mid          0.287
_exptl_crystal_size_min          0.253
_exptl_special_details           
;
One distinct cell was identified using APEX3 (Bruker, 2019). Six frame series 
were integrated and filtered for statistical outliers using SAINT v8.40B 
(Bruker, 2019) then corrected for absorption by multi-scan methods using SADABS 
v2016/2 (Krause et al., 2015). During the later stages of refinement there were 
indications of possible twinning. The twin law (0 1 0), (1 0 0), (0 0 -1) 
significantly improved fitting factors and residuals and was included in the 
final refinement. Inversion twinning of both orientations was statistically 
significant and also included in the final refinement. No decay correction 
was applied. 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0266
_diffrn_reflns_av_unetI/netI     0.0111
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            40836
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.110
_diffrn_reflns_theta_min         2.393
_diffrn_ambient_temperature      100.01
_diffrn_detector                 'Bruker D8 Venture'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            'CPAD area detector'
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device       'kappa diffractometer'
_diffrn_measurement_device_type  'Bruker Kappa/PhotonII CCD'
_diffrn_measurement_method       'profile data from φ and ω scans'
_diffrn_radiation_monochromator  multi-mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_target            Mo
_diffrn_source_type              'Ius microfocus sealed tube'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.939
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.997
_reflns_number_gt                2825
_reflns_number_total             2884
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (Bruker, 2019)'
_computing_data_collection       'APEX3 V2019.11-0 (Bruker, 2019)'
_computing_data_reduction        
;
SAINT V8.40B, XPREP v2014/2, (Bruker, 2019), SADABS V2016/2 
(Krause et al., 2015) 
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT-2018-2 (Sheldrick, 2015b)'
_refine_diff_density_max         1.097
_refine_diff_density_min         -0.367
_refine_diff_density_rms         0.097
_refine_ls_abs_structure_details 
;
 Flack x determined using 1338 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.307(13)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         2884
_refine_ls_number_restraints     392
_refine_ls_R_factor_all          0.0629
_refine_ls_R_factor_gt           0.0622
_refine_ls_restrained_S_all      1.116
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1354P)²+0.8804P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1723
_refine_ls_wR_factor_ref         0.1736
_refine_special_details          
;
 Refined as a 4-component twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 1(10)
 0.2(2) 0(10) 0.2(2)
2. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3. Restrained distances
 N1-C1 \\sim N1-C2 \\sim N1-C1A \\sim N1-C2A
 with sigma of 0.01
 C1-C2_$1 \\sim C1A-C2A_$1
 with sigma of 0.01
 C3-C4 \\sim C3-C5 \\sim C3-C4A \\sim C3-C5A
 with sigma of 0.01
 C7-C8 \\sim C7-C9 \\sim C7-C10 \\sim C7-C8A \\sim C7-C9A \\sim C7-C10A
 with sigma of 0.01
 C8-C9 \\sim C9-C10 \\sim C10-C8 \\sim C8A-C9A \\sim C9A-C10A \\sim C10A-C8A
 with sigma of 0.02
 P1-F1 \\sim P1-F2 \\sim P1-F1A \\sim P1-F2A
 with sigma of 0.01
 P2-F3 \\sim P2-F4 \\sim P2-F3A \\sim P2-F4A
 with sigma of 0.01
 F3-F3_$2 \\sim F3-F3_$3 \\sim F3A-F3A_$2 \\sim F3A-F3A_$3 \\sim F4-F4_$2 \\sim
F4-F4_$3 \\sim F4A-
 F4A_$2 \\sim F4A-F4A_$3 \\sim F4-F3 \\sim F4A-F3A
 with sigma of 0.02
4. Uiso/Uaniso restraints and constraints
C4 \\sim C5 \\sim C4A \\sim C5A: within 2A with sigma of 0.005 and sigma for
terminal atoms of 0.01
C8 \\sim C9 \\sim C10 \\sim C8A \\sim C9A \\sim C10A: within 2A with sigma of
0.01 and sigma for terminal atoms of 0.02
F1 \\sim F2 \\sim F1A \\sim F2A: within 2A with sigma of 0.005 and sigma for
terminal atoms of 0.01
F3 \\sim F4 \\sim F3A \\sim F4A: within 2A with sigma of 0.005 and sigma for
terminal atoms of 0.01
Uanis(F3) \\sim Ueq, Uanis(F4) \\sim Ueq, Uanis(F3A) \\sim Ueq, Uanis(F4A)
\\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.01
Uanis(C1) = Uanis(C1A) = Uanis(C2) = Uanis(C2A)
Uanis(C4A) = Uanis(C5A)
5. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
6. Others
 Sof(C1A)=Sof(H1AA)=Sof(H1AB)=Sof(C2A)=Sof(H2AA)=Sof(H2AB)=Sof(H3B)=Sof(C4A)=
 Sof(H4AA)=Sof(H4AB)=Sof(H4AC)=Sof(C5A)=Sof(H5AA)=Sof(H5AB)=Sof(H5AC)=1-FVAR(1)
 Sof(C1)=Sof(H1A)=Sof(H1B)=Sof(C2)=Sof(H2A)=Sof(H2B)=Sof(H3A)=Sof(C4)=Sof(H4A)=
 Sof(H4B)=Sof(H4C)=Sof(C5)=Sof(H5A)=Sof(H5B)=Sof(H5C)=FVAR(1)
 Sof(C8A)=Sof(H8AA)=Sof(H8AB)=Sof(H8AC)=Sof(C9A)=Sof(H9AA)=Sof(H9AB)=Sof(H9AC)=
 Sof(C10A)=Sof(H10D)=Sof(H10E)=Sof(H10F)=1-FVAR(2)
 Sof(C8)=Sof(H8A)=Sof(H8B)=Sof(H8C)=Sof(C9)=Sof(H9A)=Sof(H9B)=Sof(H9C)=
 Sof(C10)=Sof(H10A)=Sof(H10B)=Sof(H10C)=FVAR(2)
 Sof(F1A)=Sof(F2A)=1-FVAR(3)
 Sof(F1)=Sof(F2)=FVAR(3)
 Sof(F3A)=Sof(F4A)=1-FVAR(4)
 Sof(F3)=Sof(F4)=FVAR(4)
7.a Ternary CH refined with riding coordinates:
 C3(H3A), C3(H3B)
7.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B), C1A(H1AA,H1AB), C2A(H2AA,H2AB)
7.c Me refined with riding coordinates:
 C4(H4A,H4B,H4C), C5(H5A,H5B,H5C), C4A(H4AA,H4AB,H4AC), C5A(H5AA,H5AB,H5AC),
 C8(H8A,H8B,H8C), C9(H9A,H9B,H9C), C10(H10A,H10B,H10C), C8A(H8AA,H8AB,H8AC),
 C9A(H9AA,H9AB,H9AC), C10A(H10D,H10E,H10F)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Ni1 Ni 0.6667 0.3333 0.35655(8) 0.0270(3) Uani 1 3 d S TU P C .
P1 P 0.6667 0.3333 0.0043(2) 0.0653(11) Uani 1 3 d DS TU P . .
P2 P 0.0000 0.0000 0.25058(16) 0.0494(7) Uani 1 3 d DS TU P . .
F1 F 0.6720(16) 0.2181(12) 0.0548(5) 0.074(3) Uani 0.715(19) 1 d D U . A 1
F2 F 0.5471(14) 0.2195(14) -0.0474(6) 0.083(3) Uani 0.715(19) 1 d D U . A 1
F1A F 0.793(3) 0.357(4) 0.0552(14) 0.079(6) Uani 0.285(19) 1 d D U . A 2
F2A F 0.541(3) 0.316(5) -0.0466(18) 0.089(6) Uani 0.285(19) 1 d D U . A 2
F3 F 0.1064(14) 0.1241(11) 0.2992(6) 0.128(4) Uani 0.76(2) 1 d D U . B 1
F4 F -0.0414(16) 0.0926(13) 0.2053(6) 0.107(4) Uani 0.76(2) 1 d D U . B 1
F3A F 0.022(6) 0.127(3) 0.2980(12) 0.115(6) Uani 0.24(2) 1 d D U . B 2
F4A F -0.118(3) 0.001(6) 0.2051(12) 0.112(7) Uani 0.24(2) 1 d D U . B 2
N1 N 0.5702(7) 0.4101(6) 0.2844(3) 0.0397(11) Uani 1 1 d D U . . .
N2 N 0.4366(8) 0.2258(13) 0.4719(4) 0.067(2) Uani 1 1 d . U . . .
C1 C 0.4550(11) 0.2700(10) 0.2541(6) 0.0358(13) Uani 0.718(11) 1 d D U . C 1
H1A H 0.3876 0.2192 0.2939 0.043 Uiso 0.718(11) 1 calc R . . C 1
H1B H 0.4049 0.2876 0.2144 0.043 Uiso 0.718(11) 1 calc R . . C 1
C2 C 0.6715(10) 0.4903(11) 0.2248(5) 0.0358(13) Uani 0.718(11) 1 d D U . C 1
H2A H 0.6563 0.4294 0.1819 0.043 Uiso 0.718(11) 1 calc R . . C 1
H2B H 0.6586 0.5682 0.2086 0.043 Uiso 0.718(11) 1 calc R . . C 1
C1A C 0.459(3) 0.299(2) 0.2367(14) 0.0358(13) Uani 0.282(11) 1 d D U . C 2
H1AA H 0.3659 0.2796 0.2518 0.043 Uiso 0.282(11) 1 calc R . . C 2
H1AB H 0.4740 0.3268 0.1843 0.043 Uiso 0.282(11) 1 calc R . . C 2
C2A C 0.701(2) 0.526(2) 0.2484(15) 0.0358(13) Uani 0.282(11) 1 d D U . C 2
H2AA H 0.6704 0.5355 0.1987 0.043 Uiso 0.282(11) 1 calc R . . C 2
H2AB H 0.7199 0.6107 0.2754 0.043 Uiso 0.282(11) 1 calc R . . C 2
C3 C 0.5052(10) 0.4854(11) 0.3200(5) 0.0506(16) Uani 1 1 d D U . . .
H3A H 0.4551 0.4334 0.3652 0.061 Uiso 0.718(11) 1 calc R . . C 1
H3B H 0.5869 0.5583 0.3477 0.061 Uiso 0.282(11) 1 calc R . . C 2
C4 C 0.6139(13) 0.6329(12) 0.3422(11) 0.067(3) Uani 0.718(11) 1 d D U . C 1
H4A H 0.5678 0.6788 0.3652 0.101 Uiso 0.718(11) 1 calc R . . C 1
H4B H 0.6791 0.6294 0.3771 0.101 Uiso 0.718(11) 1 calc R . . C 1
H4C H 0.6645 0.6850 0.2984 0.101 Uiso 0.718(11) 1 calc R . . C 1
C5 C 0.4011(14) 0.4993(16) 0.2697(9) 0.059(3) Uani 0.718(11) 1 d D U . C 1
H5A H 0.3623 0.5492 0.2958 0.089 Uiso 0.718(11) 1 calc R . . C 1
H5B H 0.4489 0.5509 0.2252 0.089 Uiso 0.718(11) 1 calc R . . C 1
H5C H 0.3260 0.4067 0.2560 0.089 Uiso 0.718(11) 1 calc R . . C 1
C4A C 0.484(5) 0.577(4) 0.264(2) 0.068(4) Uani 0.282(11) 1 d D U . C 2
H4AA H 0.4415 0.6250 0.2888 0.102 Uiso 0.282(11) 1 calc R . . C 2
H4AB H 0.5740 0.6458 0.2435 0.102 Uiso 0.282(11) 1 calc R . . C 2
H4AC H 0.4231 0.5189 0.2244 0.102 Uiso 0.282(11) 1 calc R . . C 2
C5A C 0.415(4) 0.395(3) 0.3848(18) 0.068(4) Uani 0.282(11) 1 d D U . C 2
H5AA H 0.3712 0.4422 0.4091 0.102 Uiso 0.282(11) 1 calc R . . C 2
H5AB H 0.3432 0.3050 0.3661 0.102 Uiso 0.282(11) 1 calc R . . C 2
H5AC H 0.4739 0.3818 0.4201 0.102 Uiso 0.282(11) 1 calc R . . C 2
C6 C 0.5145(9) 0.2598(18) 0.4269(4) 0.063(2) Uani 1 1 d . U . . .
C7 C 0.3327(9) 0.1742(11) 0.5310(6) 0.079(3) Uani 1 1 d D U . . .
C8 C 0.322(2) 0.0417(17) 0.5583(11) 0.086(5) Uani 0.653(19) 1 d D U . D 1
H8A H 0.2533 0.0034 0.5980 0.129 Uiso 0.653(19) 1 calc R . . D 1
H8B H 0.2929 -0.0254 0.5179 0.129 Uiso 0.653(19) 1 calc R . . D 1
H8C H 0.4125 0.0606 0.5768 0.129 Uiso 0.653(19) 1 calc R . . D 1
C9 C 0.381(2) 0.286(2) 0.5895(9) 0.098(6) Uani 0.653(19) 1 d D U . D 1
H9A H 0.3129 0.2538 0.6296 0.146 Uiso 0.653(19) 1 calc R . . D 1
H9B H 0.4711 0.3054 0.6086 0.146 Uiso 0.653(19) 1 calc R . . D 1
H9C H 0.3892 0.3706 0.5680 0.146 Uiso 0.653(19) 1 calc R . . D 1
C10 C 0.205(2) 0.155(3) 0.4902(15) 0.109(6) Uani 0.653(19) 1 d D U . D 1
H10A H 0.1262 0.1205 0.5242 0.163 Uiso 0.653(19) 1 calc R . . D 1
H10B H 0.2236 0.2449 0.4700 0.163 Uiso 0.653(19) 1 calc R . . D 1
H10C H 0.1825 0.0888 0.4500 0.163 Uiso 0.653(19) 1 calc R . . D 1
C8A C 0.414(3) 0.156(4) 0.5931(15) 0.089(7) Uani 0.347(19) 1 d D U . D 2
H8AA H 0.3558 0.1212 0.6370 0.134 Uiso 0.347(19) 1 calc R . . D 2
H8AB H 0.4432 0.0896 0.5780 0.134 Uiso 0.347(19) 1 calc R . . D 2
H8AC H 0.4968 0.2458 0.6041 0.134 Uiso 0.347(19) 1 calc R . . D 2
C9A C 0.295(3) 0.283(3) 0.5515(17) 0.085(7) Uani 0.347(19) 1 d D U . D 2
H9AA H 0.2252 0.2470 0.5909 0.127 Uiso 0.347(19) 1 calc R . . D 2
H9AB H 0.3776 0.3671 0.5684 0.127 Uiso 0.347(19) 1 calc R . . D 2
H9AC H 0.2561 0.3049 0.5084 0.127 Uiso 0.347(19) 1 calc R . . D 2
C10A C 0.208(3) 0.034(3) 0.512(2) 0.094(9) Uani 0.347(19) 1 d D U . D 2
H10D H 0.1410 0.0020 0.5519 0.141 Uiso 0.347(19) 1 calc R . . D 2
H10E H 0.1646 0.0422 0.4666 0.141 Uiso 0.347(19) 1 calc R . . D 2
H10F H 0.2393 -0.0339 0.5036 0.141 Uiso 0.347(19) 1 calc R . . D 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ni1 N1 2.125(5) 3_665 ?
Ni1 N1 2.125(5) . ?
Ni1 N1 2.125(5) 2_655 ?
Ni1 C6 1.946(8) 2_655 ?
Ni1 C6 1.946(8) . ?
Ni1 C6 1.946(8) 3_665 ?
P1 F1 1.602(8) . ?
P1 F1 1.602(8) 2_655 ?
P1 F1 1.602(8) 3_665 ?
P1 F2 1.603(9) 2_655 ?
P1 F2 1.603(9) 3_665 ?
P1 F2 1.603(9) . ?
P1 F1A 1.594(13) 3_665 ?
P1 F1A 1.594(13) . ?
P1 F1A 1.594(13) 2_655 ?
P1 F2A 1.610(13) 3_665 ?
P1 F2A 1.610(13) . ?
P1 F2A 1.610(13) 2_655 ?
P2 F3 1.566(9) 3 ?
P2 F3 1.566(9) 2 ?
P2 F3 1.566(9) . ?
P2 F4 1.557(8) 3 ?
P2 F4 1.557(8) 2 ?
P2 F4 1.557(8) . ?
P2 F3A 1.565(12) . ?
P2 F3A 1.565(12) 3 ?
P2 F3A 1.565(12) 2 ?
P2 F4A 1.555(12) 3 ?
P2 F4A 1.555(12) 2 ?
P2 F4A 1.555(12) . ?
N1 C1 1.541(10) . ?
N1 C2 1.495(9) . ?
N1 C1A 1.509(13) . ?
N1 C2A 1.524(13) . ?
N1 C3 1.500(8) . ?
N2 C6 1.112(12) . ?
N2 C7 1.467(11) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C1 C2 1.493(13) 2_655 ?
C2 C1 1.493(13) 3_665 ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C1A H1AA 0.9900 . ?
C1A H1AB 0.9900 . ?
C1A C2A 1.478(16) 2_655 ?
C2A C1A 1.478(16) 3_665 ?
C2A H2AA 0.9900 . ?
C2A H2AB 0.9900 . ?
C3 H3A 1.0000 . ?
C3 H3B 1.0000 . ?
C3 C4 1.526(12) . ?
C3 C5 1.542(11) . ?
C3 C4A 1.538(15) . ?
C3 C5A 1.546(15) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C4A H4AA 0.9800 . ?
C4A H4AB 0.9800 . ?
C4A H4AC 0.9800 . ?
C5A H5AA 0.9800 . ?
C5A H5AB 0.9800 . ?
C5A H5AC 0.9800 . ?
C7 C8 1.502(15) . ?
C7 C9 1.516(15) . ?
C7 C10 1.523(15) . ?
C7 C8A 1.525(16) . ?
C7 C9A 1.515(16) . ?
C7 C10A 1.523(16) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C8A H8AA 0.9800 . ?
C8A H8AB 0.9800 . ?
C8A H8AC 0.9800 . ?
C9A H9AA 0.9800 . ?
C9A H9AB 0.9800 . ?
C9A H9AC 0.9800 . ?
C10A H10D 0.9800 . ?
C10A H10E 0.9800 . ?
C10A H10F 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 Ni1 N1 85.9(2) 3_665 . ?
N1 Ni1 N1 85.9(2) 2_655 . ?
N1 Ni1 N1 85.9(2) 2_655 3_665 ?
C6 Ni1 N1 93.9(4) . . ?
C6 Ni1 N1 175.2(5) . 3_665 ?
C6 Ni1 N1 98.9(5) . 2_655 ?
C6 Ni1 N1 93.9(4) 2_655 2_655 ?
C6 Ni1 N1 98.9(5) 2_655 3_665 ?
C6 Ni1 N1 175.2(5) 2_655 . ?
C6 Ni1 N1 98.9(5) 3_665 . ?
C6 Ni1 N1 175.2(5) 3_665 2_655 ?
C6 Ni1 N1 93.9(4) 3_665 3_665 ?
C6 Ni1 C6 81.4(4) 3_665 . ?
C6 Ni1 C6 81.4(4) 2_655 . ?
C6 Ni1 C6 81.4(4) 2_655 3_665 ?
F1 P1 F1 90.4(5) . 2_655 ?
F1 P1 F1 90.4(5) . 3_665 ?
F1 P1 F1 90.4(5) 2_655 3_665 ?
F1 P1 F2 87.6(7) 3_665 . ?
F1 P1 F2 87.6(7) 2_655 3_665 ?
F1 P1 F2 93.0(8) 3_665 3_665 ?
F1 P1 F2 176.1(8) 3_665 2_655 ?
F1 P1 F2 87.6(7) . 2_655 ?
F1 P1 F2 93.0(8) . . ?
F1 P1 F2 176.1(8) 2_655 . ?
F1 P1 F2 176.1(8) . 3_665 ?
F1 P1 F2 93.0(8) 2_655 2_655 ?
F2 P1 F2 89.1(7) . 3_665 ?
F2 P1 F2 89.1(7) 2_655 3_665 ?
F2 P1 F2 89.1(7) 2_655 . ?
F1A P1 F1A 89.8(15) . 3_665 ?
F1A P1 F1A 89.8(15) 3_665 2_655 ?
F1A P1 F1A 89.8(15) . 2_655 ?
F1A P1 F2A 178(2) . . ?
F1A P1 F2A 88.4(18) . 3_665 ?
F1A P1 F2A 88.4(18) 2_655 . ?
F1A P1 F2A 88.4(18) 3_665 2_655 ?
F1A P1 F2A 178(2) 2_655 2_655 ?
F1A P1 F2A 91.7(19) . 2_655 ?
F1A P1 F2A 91.7(19) 2_655 3_665 ?
F1A P1 F2A 178(2) 3_665 3_665 ?
F1A P1 F2A 91.7(19) 3_665 . ?
F2A P1 F2A 90.2(19) 3_665 . ?
F2A P1 F2A 90.2(19) 2_655 3_665 ?
F2A P1 F2A 90.2(19) 2_655 . ?
F3 P2 F3 91.3(6) . 3 ?
F3 P2 F3 91.3(6) 2 3 ?
F3 P2 F3 91.3(6) . 2 ?
F4 P2 F3 171.3(8) 3 2 ?
F4 P2 F3 93.3(7) 3 3 ?
F4 P2 F3 81.3(7) 2 3 ?
F4 P2 F3 171.3(8) . 3 ?
F4 P2 F3 81.3(7) 3 . ?
F4 P2 F3 171.3(8) 2 . ?
F4 P2 F3 81.3(7) . 2 ?
F4 P2 F3 93.3(7) . . ?
F4 P2 F3 93.3(7) 2 2 ?
F4 P2 F4 94.6(6) 2 3 ?
F4 P2 F4 94.6(6) . 3 ?
F4 P2 F4 94.6(6) 2 . ?
F3A P2 F3A 92.5(11) . 2 ?
F3A P2 F3A 92.5(11) . 3 ?
F3A P2 F3A 92.5(11) 3 2 ?
F4A P2 F3A 81(2) . 2 ?
F4A P2 F3A 81(2) 3 . ?
F4A P2 F3A 173(2) 2 . ?
F4A P2 F3A 173(2) 3 2 ?
F4A P2 F3A 92.1(12) . . ?
F4A P2 F3A 173(2) . 3 ?
F4A P2 F3A 92.1(12) 2 2 ?
F4A P2 F3A 92.1(12) 3 3 ?
F4A P2 F3A 81(2) 2 3 ?
F4A P2 F4A 94.3(11) . 3 ?
F4A P2 F4A 94.3(11) 2 3 ?
F4A P2 F4A 94.3(11) 2 . ?
C1 N1 Ni1 98.4(5) . . ?
C2 N1 Ni1 107.9(4) . . ?
C2 N1 C1 110.0(7) . . ?
C2 N1 C3 114.2(7) . . ?
C1A N1 Ni1 113.2(9) . . ?
C1A N1 C2A 119.2(15) . . ?
C2A N1 Ni1 98.3(11) . . ?
C3 N1 Ni1 116.0(5) . . ?
C3 N1 C1 109.2(7) . . ?
C3 N1 C1A 106.4(12) . . ?
C3 N1 C2A 103.7(12) . . ?
C6 N2 C7 177.2(18) . . ?
N1 C1 H1A 109.0 . . ?
N1 C1 H1B 109.0 . . ?
H1A C1 H1B 107.8 . . ?
C2 C1 N1 112.9(8) 2_655 . ?
C2 C1 H1A 109.0 2_655 . ?
C2 C1 H1B 109.0 2_655 . ?
N1 C2 H2A 110.0 . . ?
N1 C2 H2B 110.0 . . ?
C1 C2 N1 108.5(7) 3_665 . ?
C1 C2 H2A 110.0 3_665 . ?
C1 C2 H2B 110.0 3_665 . ?
H2A C2 H2B 108.4 . . ?
N1 C1A H1AA 110.8 . . ?
N1 C1A H1AB 110.8 . . ?
H1AA C1A H1AB 108.9 . . ?
C2A C1A N1 104.8(18) 2_655 . ?
C2A C1A H1AA 110.8 2_655 . ?
C2A C1A H1AB 110.8 2_655 . ?
N1 C2A H2AA 104.5 . . ?
N1 C2A H2AB 104.5 . . ?
C1A C2A N1 131(2) 3_665 . ?
C1A C2A H2AA 104.5 3_665 . ?
C1A C2A H2AB 104.5 3_665 . ?
H2AA C2A H2AB 105.7 . . ?
N1 C3 H3A 108.5 . . ?
N1 C3 H3B 100.0 . . ?
N1 C3 C4 111.7(8) . . ?
N1 C3 C5 113.3(8) . . ?
N1 C3 C4A 111.2(17) . . ?
N1 C3 C5A 107.7(15) . . ?
C4 C3 H3A 108.5 . . ?
C4 C3 C5 106.3(10) . . ?
C5 C3 H3A 108.5 . . ?
C4A C3 H3B 100.0 . . ?
C4A C3 C5A 132(2) . . ?
C5A C3 H3B 100.0 . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C3 C5 H5A 109.5 . . ?
C3 C5 H5B 109.5 . . ?
C3 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C3 C4A H4AA 109.5 . . ?
C3 C4A H4AB 109.5 . . ?
C3 C4A H4AC 109.5 . . ?
H4AA C4A H4AB 109.5 . . ?
H4AA C4A H4AC 109.5 . . ?
H4AB C4A H4AC 109.5 . . ?
C3 C5A H5AA 109.5 . . ?
C3 C5A H5AB 109.5 . . ?
C3 C5A H5AC 109.5 . . ?
H5AA C5A H5AB 109.5 . . ?
H5AA C5A H5AC 109.5 . . ?
H5AB C5A H5AC 109.5 . . ?
N2 C6 Ni1 173.4(10) . . ?
N2 C7 C8 106.7(13) . . ?
N2 C7 C9 107.9(10) . . ?
N2 C7 C10 101.3(12) . . ?
N2 C7 C8A 100.9(15) . . ?
N2 C7 C9A 110.4(14) . . ?
N2 C7 C10A 111.4(17) . . ?
C8 C7 C9 113.2(11) . . ?
C8 C7 C10 114.6(11) . . ?
C9 C7 C10 112.1(12) . . ?
C9A C7 C8A 110.2(13) . . ?
C9A C7 C10A 113.8(14) . . ?
C10A C7 C8A 109.4(14) . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C7 C9 H9A 109.5 . . ?
C7 C9 H9B 109.5 . . ?
C7 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C7 C10 H10A 109.5 . . ?
C7 C10 H10B 109.5 . . ?
C7 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C7 C8A H8AA 109.5 . . ?
C7 C8A H8AB 109.5 . . ?
C7 C8A H8AC 109.5 . . ?
H8AA C8A H8AB 109.5 . . ?
H8AA C8A H8AC 109.5 . . ?
H8AB C8A H8AC 109.5 . . ?
C7 C9A H9AA 109.5 . . ?
C7 C9A H9AB 109.5 . . ?
C7 C9A H9AC 109.5 . . ?
H9AA C9A H9AB 109.5 . . ?
H9AA C9A H9AC 109.5 . . ?
H9AB C9A H9AC 109.5 . . ?
C7 C10A H10D 109.5 . . ?
C7 C10A H10E 109.5 . . ?
C7 C10A H10F 109.5 . . ?
H10D C10A H10E 109.5 . . ?
H10D C10A H10F 109.5 . . ?
H10E C10A H10F 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Ni1 N1 C1 C2 -52.4(9) . . . 2_655 ?
Ni1 N1 C2 C1 -26.9(9) . . . 3_665 ?
Ni1 N1 C1A C2A -10(3) . . . 2_655 ?
Ni1 N1 C2A C1A 27(3) . . . 3_665 ?
Ni1 N1 C3 C4 77.4(11) . . . . ?
Ni1 N1 C3 C5 -162.6(8) . . . . ?
Ni1 N1 C3 C4A 161(2) . . . . ?
Ni1 N1 C3 C5A -48.2(19) . . . . ?
C1 N1 C2 C1 -133.2(8) . . . 3_665 ?
C1 N1 C3 C4 -172.6(10) . . . . ?
C1 N1 C3 C5 -52.6(11) . . . . ?
C2 N1 C1 C2 60.1(11) . . . 2_655 ?
C2 N1 C3 C4 -48.9(11) . . . . ?
C2 N1 C3 C5 71.0(12) . . . . ?
C1A N1 C2A C1A -96(4) . . . 3_665 ?
C1A N1 C3 C4A -72(2) . . . . ?
C1A N1 C3 C5A 79(2) . . . . ?
C2A N1 C1A C2A 105(2) . . . 2_655 ?
C2A N1 C3 C4A 54(2) . . . . ?
C2A N1 C3 C5A -155(2) . . . . ?
C3 N1 C1 C2 -173.8(9) . . . 2_655 ?
C3 N1 C2 C1 103.6(9) . . . 3_665 ?
C3 N1 C1A C2A -138(2) . . . 2_655 ?
C3 N1 C2A C1A 146(3) . . . 3_665 ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 1(10)
2 0.2(2)
3 0(10)
4 0.2(2)

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

data_14_a
_database_code_depnum_ccdc_archive 'CCDC 2167752'
loop_
_audit_author_name
_audit_author_address
'Liviu Mirica'
;University of Illinois at Urbana Champaign
United States of America
;
_audit_update_record             
;
2022-04-20 deposited with the CCDC.	2022-06-09 downloaded from the CCDC.
;
_audit_creation_date             2020-06-04
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelxl_version_number           2014/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H36 N5 Ni O2, F6 P, C2 H3 N'
_chemical_formula_sum            'C18 H39 F6 N6 Ni O2 P'
_chemical_formula_weight         575.23
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   8.4457(2)
_cell_length_b                   14.5310(4)
_cell_length_c                   20.9391(6)
_cell_angle_alpha                90
_cell_angle_beta                 93.8700(10)
_cell_angle_gamma                90
_cell_volume                     2563.88(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    18373
_cell_measurement_temperature    100
_cell_measurement_theta_max      28.29
_cell_measurement_theta_min      2.40
_shelx_estimated_absorpt_T_max   0.954
_shelx_estimated_absorpt_T_min   0.782
_exptl_absorpt_coefficient_mu    0.890
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6967
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0800 before and 0.0519 after correction.
The Ratio of minimum to maximum transmission is 0.9343.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            blue
_exptl_crystal_colour_primary    blue
_exptl_crystal_density_diffrn    1.490
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1208
_exptl_crystal_preparation       
'Dissolved in MeCN and crystal grown through Et2O vapor diffusion.'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Acetonitrile and Diethylether'
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.167
_exptl_crystal_size_min          0.054
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0393
_diffrn_reflns_av_unetI/netI     0.0222
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            47944
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.301
_diffrn_reflns_theta_min         2.401
_diffrn_ambient_temperature      100.0
_diffrn_detector                 'Bruker D8 Venture'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            'CPAD area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'kappa diffractometer'
_diffrn_measurement_device_type  'Bruker Kappa/PhotonII CCD'
_diffrn_measurement_method       'profile data from φ and ω scans'
_diffrn_radiation_monochromator  multi-mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_target            Mo
_diffrn_source_type              'Ius microfocus sealed tube'
_diffrn_special_details          ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5633
_reflns_number_total             6379
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_refine_diff_density_max         1.036
_refine_diff_density_min         -0.485
_refine_diff_density_rms         0.065
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     315
_refine_ls_number_reflns         6379
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0408
_refine_ls_R_factor_gt           0.0351
_refine_ls_restrained_S_all      1.025
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0384P)²+2.5614P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0848
_refine_ls_wR_factor_ref         0.0882
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7), C10(H10), C13(H13)
2.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C5(H5A,H5B), C6(H6A,H6B)
2.c Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C9(H9A,H9B,H9C), C11(H11A,H11B,H11C), C12(H12A,H12B,H12C),
 C14(H14A,H14B,H14C), C15(H15A,H15B,H15C), C16(H16A,H16B,H16C), C18(H18A,H18B,
 H18C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Ni1 Ni 0.55311(2) 0.71350(2) 0.45034(2) 0.01420(7) Uani 1 1 d . . . . .
O1 O 0.43584(14) 0.61578(9) 0.49196(6) 0.0210(3) Uani 1 1 d . . . . .
C1 C 0.5651(2) 0.72006(12) 0.31131(8) 0.0216(4) Uani 1 1 d . . . . .
H1A H 0.5006 0.6997 0.2727 0.026 Uiso 1 1 calc R . . . .
H1B H 0.6759 0.7277 0.2995 0.026 Uiso 1 1 calc R . . . .
N1 N 0.56798(18) 0.83501(10) 0.39917(7) 0.0193(3) Uani 1 1 d . . . . .
N2 N 0.79707(16) 0.70864(10) 0.45653(7) 0.0179(3) Uani 1 1 d . . . . .
O2 O 0.53533(16) 0.76732(9) 0.53760(6) 0.0224(3) Uani 1 1 d . . . . .
C2 C 0.5027(2) 0.81255(13) 0.33333(9) 0.0235(4) Uani 1 1 d . . . . .
H2A H 0.5328 0.8614 0.3035 0.028 Uiso 1 1 calc R . . . .
H2B H 0.3854 0.8104 0.3324 0.028 Uiso 1 1 calc R . . . .
N3 N 0.56019(16) 0.64779(10) 0.36174(7) 0.0165(3) Uani 1 1 d . . . . .
C3 C 0.7415(2) 0.85702(13) 0.39946(10) 0.0248(4) Uani 1 1 d . . . . .
H3A H 0.7565 0.9243 0.4039 0.030 Uiso 1 1 calc R . . . .
H3B H 0.7817 0.8381 0.3581 0.030 Uiso 1 1 calc R . . . .
N4 N 0.46890(17) 0.70553(11) 0.57358(7) 0.0201(3) Uani 1 1 d . . . . .
C4 C 0.8364(2) 0.80869(12) 0.45361(10) 0.0235(4) Uani 1 1 d . . . . .
H4A H 0.9511 0.8158 0.4476 0.028 Uiso 1 1 calc R . . . .
H4B H 0.8144 0.8381 0.4947 0.028 Uiso 1 1 calc R . . . .
N5 N 0.41638(17) 0.62804(11) 0.55283(7) 0.0210(3) Uani 1 1 d . . . . .
C5 C 0.8467(2) 0.65768(13) 0.39909(9) 0.0208(3) Uani 1 1 d . . . . .
H5A H 0.9401 0.6189 0.4116 0.025 Uiso 1 1 calc R . . . .
H5B H 0.8784 0.7024 0.3666 0.025 Uiso 1 1 calc R . . . .
C6 C 0.71342(19) 0.59705(12) 0.36992(9) 0.0196(3) Uani 1 1 d . . . . .
H6A H 0.7426 0.5743 0.3277 0.023 Uiso 1 1 calc R . . . .
H6B H 0.7003 0.5431 0.3979 0.023 Uiso 1 1 calc R . . . .
C7 C 0.4253(2) 0.58000(12) 0.34907(9) 0.0204(3) Uani 1 1 d . . . . .
H7 H 0.4273 0.5373 0.3865 0.025 Uiso 1 1 calc R . . . .
C8 C 0.4412(2) 0.52091(14) 0.28951(10) 0.0292(4) Uani 1 1 d . . . . .
H8A H 0.3561 0.4750 0.2864 0.044 Uiso 1 1 calc GR . . . .
H8B H 0.5443 0.4897 0.2926 0.044 Uiso 1 1 calc GR . . . .
H8C H 0.4334 0.5602 0.2514 0.044 Uiso 1 1 calc GR . . . .
C9 C 0.2655(2) 0.62885(14) 0.34570(10) 0.0253(4) Uani 1 1 d . . . . .
H9A H 0.2572 0.6663 0.3842 0.038 Uiso 1 1 calc GR . . . .
H9B H 0.1801 0.5831 0.3429 0.038 Uiso 1 1 calc GR . . . .
H9C H 0.2564 0.6686 0.3078 0.038 Uiso 1 1 calc GR . . . .
C10 C 0.4785(2) 0.91258(13) 0.42821(9) 0.0257(4) Uani 1 1 d . . . . .
H10 H 0.5339 0.9268 0.4708 0.031 Uiso 1 1 calc R . . . .
C11 C 0.3088(2) 0.88478(15) 0.44019(10) 0.0314(4) Uani 1 1 d . . . . .
H11A H 0.2460 0.8801 0.3992 0.047 Uiso 1 1 calc GR . . . .
H11B H 0.2617 0.9313 0.4670 0.047 Uiso 1 1 calc GR . . . .
H11C H 0.3096 0.8251 0.4620 0.047 Uiso 1 1 calc GR . . . .
C12 C 0.4776(3) 1.00114(14) 0.38843(11) 0.0352(5) Uani 1 1 d . . . . .
H12A H 0.5868 1.0178 0.3802 0.053 Uiso 1 1 calc GR . . . .
H12B H 0.4294 1.0510 0.4120 0.053 Uiso 1 1 calc GR . . . .
H12C H 0.4160 0.9913 0.3476 0.053 Uiso 1 1 calc GR . . . .
C13 C 0.8664(2) 0.66850(13) 0.51873(9) 0.0211(3) Uani 1 1 d . . . . .
H13 H 0.8198 0.7035 0.5541 0.025 Uiso 1 1 calc R . . . .
C14 C 1.0467(2) 0.67886(15) 0.52805(10) 0.0281(4) Uani 1 1 d . . . . .
H14A H 1.0964 0.6486 0.4927 0.042 Uiso 1 1 calc GR . . . .
H14B H 1.0846 0.6503 0.5686 0.042 Uiso 1 1 calc GR . . . .
H14C H 1.0745 0.7443 0.5288 0.042 Uiso 1 1 calc GR . . . .
C15 C 0.8180(2) 0.56829(13) 0.52577(10) 0.0235(4) Uani 1 1 d . . . . .
H15A H 0.7022 0.5632 0.5205 0.035 Uiso 1 1 calc GR . . . .
H15B H 0.8551 0.5460 0.5683 0.035 Uiso 1 1 calc GR . . . .
H15C H 0.8656 0.5312 0.4930 0.035 Uiso 1 1 calc GR . . . .
C16 C 0.4557(3) 0.72889(15) 0.64087(10) 0.0309(4) Uani 1 1 d . . . . .
H16A H 0.5620 0.7325 0.6626 0.046 Uiso 1 1 calc GR . . . .
H16B H 0.3939 0.6814 0.6612 0.046 Uiso 1 1 calc GR . . . .
H16C H 0.4024 0.7885 0.6439 0.046 Uiso 1 1 calc GR . . . .
F1 F 0.85503(18) 0.83358(12) 0.20706(13) 0.0808(7) Uani 1 1 d . . . . .
P1 P 1.01994(6) 0.87362(4) 0.23611(3) 0.02973(12) Uani 1 1 d . . . . .
F2 F 1.11399(18) 0.80059(10) 0.19632(9) 0.0551(4) Uani 1 1 d . . . . .
F3 F 1.18541(17) 0.91597(13) 0.26376(8) 0.0586(4) Uani 1 1 d . . . . .
F4 F 0.92466(17) 0.94651(11) 0.27514(7) 0.0469(4) Uani 1 1 d . . . . .
F5 F 1.0188(3) 0.80326(16) 0.29355(12) 0.1099(11) Uani 1 1 d . . . . .
F6 F 1.02145(19) 0.94474(11) 0.17873(7) 0.0488(4) Uani 1 1 d . . . . .
N6 N 1.1108(6) 0.9148(3) 0.5894(2) 0.142(2) Uani 1 1 d . . . . .
C17 C 1.0220(4) 0.9001(2) 0.62458(19) 0.0676(9) Uani 1 1 d . . . . .
C18 C 0.9088(4) 0.8807(2) 0.6697(2) 0.0785(12) Uani 1 1 d . . . . .
H18A H 0.9623 0.8533 0.7081 0.118 Uiso 1 1 calc GR . . . .
H18B H 0.8295 0.8376 0.6509 0.118 Uiso 1 1 calc GR . . . .
H18C H 0.8563 0.9379 0.6813 0.118 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ni1 O1 1.9680(12) . ?
Ni1 N1 2.0735(15) . ?
Ni1 N2 2.0569(14) . ?
Ni1 O2 2.0024(13) . ?
Ni1 N3 2.0909(14) . ?
O1 N5 1.308(2) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C1 C2 1.526(2) . ?
C1 N3 1.492(2) . ?
N1 C2 1.486(2) . ?
N1 C3 1.500(2) . ?
N1 C10 1.508(2) . ?
N2 C4 1.494(2) . ?
N2 C5 1.496(2) . ?
N2 C13 1.509(2) . ?
O2 N4 1.3212(19) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
N3 C6 1.489(2) . ?
N3 C7 1.516(2) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.516(3) . ?
N4 N5 1.276(2) . ?
N4 C16 1.461(2) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C6 1.524(2) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 H7 1.0000 . ?
C7 C8 1.527(3) . ?
C7 C9 1.522(2) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10 1.0000 . ?
C10 C11 1.526(3) . ?
C10 C12 1.533(3) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13 1.0000 . ?
C13 C14 1.529(2) . ?
C13 C15 1.522(3) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
F1 P1 1.5918(18) . ?
P1 F2 1.5938(15) . ?
P1 F3 1.5994(17) . ?
P1 F4 1.5895(14) . ?
P1 F5 1.5790(16) . ?
P1 F6 1.5855(15) . ?
N6 C17 1.107(4) . ?
C17 C18 1.417(5) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 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
O1 Ni1 N1 153.26(6) . . ?
O1 Ni1 N2 118.63(6) . . ?
O1 Ni1 O2 78.86(5) . . ?
O1 Ni1 N3 96.24(5) . . ?
N1 Ni1 N3 85.65(6) . . ?
N2 Ni1 N1 88.08(6) . . ?
N2 Ni1 N3 87.23(6) . . ?
O2 Ni1 N1 98.62(6) . . ?
O2 Ni1 N2 95.30(6) . . ?
O2 Ni1 N3 175.09(5) . . ?
N5 O1 Ni1 115.67(11) . . ?
H1A C1 H1B 107.9 . . ?
C2 C1 H1A 109.1 . . ?
C2 C1 H1B 109.1 . . ?
N3 C1 H1A 109.1 . . ?
N3 C1 H1B 109.1 . . ?
N3 C1 C2 112.29(14) . . ?
C2 N1 Ni1 105.12(11) . . ?
C2 N1 C3 110.60(14) . . ?
C2 N1 C10 111.94(14) . . ?
C3 N1 Ni1 105.83(11) . . ?
C3 N1 C10 110.80(14) . . ?
C10 N1 Ni1 112.26(11) . . ?
C4 N2 Ni1 100.88(10) . . ?
C4 N2 C5 111.94(14) . . ?
C4 N2 C13 109.70(14) . . ?
C5 N2 Ni1 107.47(10) . . ?
C5 N2 C13 112.90(14) . . ?
C13 N2 Ni1 113.35(10) . . ?
N4 O2 Ni1 108.41(10) . . ?
C1 C2 H2A 109.4 . . ?
C1 C2 H2B 109.4 . . ?
N1 C2 C1 111.08(15) . . ?
N1 C2 H2A 109.4 . . ?
N1 C2 H2B 109.4 . . ?
H2A C2 H2B 108.0 . . ?
C1 N3 Ni1 108.08(10) . . ?
C1 N3 C7 112.95(14) . . ?
C6 N3 Ni1 101.58(10) . . ?
C6 N3 C1 111.37(13) . . ?
C6 N3 C7 109.60(13) . . ?
C7 N3 Ni1 112.71(10) . . ?
N1 C3 H3A 109.3 . . ?
N1 C3 H3B 109.3 . . ?
N1 C3 C4 111.80(14) . . ?
H3A C3 H3B 107.9 . . ?
C4 C3 H3A 109.3 . . ?
C4 C3 H3B 109.3 . . ?
O2 N4 C16 117.07(15) . . ?
N5 N4 O2 123.84(15) . . ?
N5 N4 C16 119.10(16) . . ?
N2 C4 C3 111.94(15) . . ?
N2 C4 H4A 109.2 . . ?
N2 C4 H4B 109.2 . . ?
C3 C4 H4A 109.2 . . ?
C3 C4 H4B 109.2 . . ?
H4A C4 H4B 107.9 . . ?
N4 N5 O1 112.85(14) . . ?
N2 C5 H5A 109.3 . . ?
N2 C5 H5B 109.3 . . ?
N2 C5 C6 111.63(13) . . ?
H5A C5 H5B 108.0 . . ?
C6 C5 H5A 109.3 . . ?
C6 C5 H5B 109.3 . . ?
N3 C6 C5 111.87(14) . . ?
N3 C6 H6A 109.2 . . ?
N3 C6 H6B 109.2 . . ?
C5 C6 H6A 109.2 . . ?
C5 C6 H6B 109.2 . . ?
H6A C6 H6B 107.9 . . ?
N3 C7 H7 107.1 . . ?
N3 C7 C8 113.71(14) . . ?
N3 C7 C9 111.01(14) . . ?
C8 C7 H7 107.1 . . ?
C9 C7 H7 107.1 . . ?
C9 C7 C8 110.53(15) . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C7 C9 H9A 109.5 . . ?
C7 C9 H9B 109.5 . . ?
C7 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N1 C10 H10 107.2 . . ?
N1 C10 C11 111.73(16) . . ?
N1 C10 C12 113.13(16) . . ?
C11 C10 H10 107.2 . . ?
C11 C10 C12 109.96(17) . . ?
C12 C10 H10 107.2 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N2 C13 H13 107.1 . . ?
N2 C13 C14 113.39(15) . . ?
N2 C13 C15 111.25(15) . . ?
C14 C13 H13 107.1 . . ?
C15 C13 H13 107.1 . . ?
C15 C13 C14 110.67(15) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N4 C16 H16A 109.5 . . ?
N4 C16 H16B 109.5 . . ?
N4 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
F1 P1 F2 90.64(9) . . ?
F1 P1 F3 178.41(12) . . ?
F2 P1 F3 89.50(9) . . ?
F4 P1 F1 88.84(9) . . ?
F4 P1 F2 179.36(10) . . ?
F4 P1 F3 91.01(9) . . ?
F5 P1 F1 90.25(15) . . ?
F5 P1 F2 89.77(10) . . ?
F5 P1 F3 91.34(14) . . ?
F5 P1 F4 90.60(10) . . ?
F5 P1 F6 179.65(15) . . ?
F6 P1 F1 90.02(11) . . ?
F6 P1 F2 90.47(9) . . ?
F6 P1 F3 88.40(9) . . ?
F6 P1 F4 89.17(8) . . ?
N6 C17 C18 179.6(6) . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_chemical_properties_physical    Moisture-sensitive
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_14_a_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2166724'
loop_
_audit_author_name
_audit_author_address
'Liviu Mirica'
;University of Illinois at Urbana Champaign
United States of America
;
_audit_update_record             
;
2022-04-16 deposited with the CCDC.	2022-06-09 downloaded from the CCDC.
;
_audit_creation_date             2022-04-14
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelxl_version_number           2014/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C25 H51 N5 Ni, F6 P'
_chemical_formula_sum            'C25 H51 F6 N5 Ni P'
_chemical_formula_weight         625.38
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   10.6246(4)
_cell_length_b                   19.0632(6)
_cell_length_c                   15.7487(5)
_cell_angle_alpha                90
_cell_angle_beta                 93.8780(10)
_cell_angle_gamma                90
_cell_volume                     3182.42(19)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    14622
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      25.285
_cell_measurement_theta_min      2.486
_shelx_estimated_absorpt_T_max   0.962
_shelx_estimated_absorpt_T_min   0.923
_exptl_absorpt_coefficient_mu    0.717
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.7031
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0855 before and 0.0577 after correction. The Ratio of minimum to maximum transmission is 0.9435. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            green
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.305
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Block
_exptl_crystal_F_000             1332
_exptl_crystal_preparation       ?
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Acetonitrile, Diethylether'
_exptl_crystal_size_max          0.113
_exptl_crystal_size_mid          0.094
_exptl_crystal_size_min          0.055
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0577
_diffrn_reflns_av_unetI/netI     0.0251
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            58756
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.357
_diffrn_reflns_theta_min         2.485
_diffrn_ambient_temperature      100.0
_diffrn_detector                 'Bruker D8 Venture'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            'CPAD area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'kappa diffractometer'
_diffrn_measurement_device_type  Mo_Duo
_diffrn_measurement_method       'profile data from φ and ω scans'
_diffrn_radiation_monochromator  multi-mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_target            Mo
_diffrn_source_type              'Ius microfocus sealed tube'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4823
_reflns_number_total             5821
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.551
_refine_diff_density_min         -0.374
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     355
_refine_ls_number_reflns         5821
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0510
_refine_ls_R_factor_gt           0.0388
_refine_ls_restrained_S_all      1.036
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0351P)²+3.2384P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0880
_refine_ls_wR_factor_ref         0.0942
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9), C12(H12), C15(H15)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C4(H4A,H4B), C5(H5A,H5B), C6(H6A,H6B), C7(H7A,H7B), C8(H8A,H8B)
2.c Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C11(H11A,H11B,H11C), C13(H13A,H13B,H13C), C14(H14A,H14B,
 H14C), C16(H16A,H16B,H16C), C17(H17A,H17B,H17C), C19(H19A,H19B,H19C), C20(H20A,
 H20B,H20C), C21(H21A,H21B,H21C), C23(H23A,H23B,H23C), C24(H24A,H24B,H24C),
 C25(H25A,H25B,H25C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Ni1 Ni 0.26994(3) 0.47415(2) 0.24098(2) 0.02760(10) Uani 1 1 d . . . . .
N1 N 0.37807(19) 0.56793(10) 0.28346(12) 0.0278(4) Uani 1 1 d . . . . .
N2 N 0.11098(19) 0.54790(11) 0.23585(13) 0.0303(4) Uani 1 1 d . . . . .
N3 N 0.2390(2) 0.47030(11) 0.37747(13) 0.0367(5) Uani 1 1 d . . . . .
N4 N 0.4323(2) 0.41468(11) 0.10924(14) 0.0368(5) Uani 1 1 d . . . . .
N5 N 0.1075(2) 0.34901(11) 0.17809(13) 0.0337(5) Uani 1 1 d . . . . .
C1 C 0.3771(2) 0.44284(13) 0.16090(16) 0.0335(6) Uani 1 1 d . . . . .
C2 C 0.1612(3) 0.39589(14) 0.20909(17) 0.0377(6) Uani 1 1 d . . . . .
C3 C 0.3031(2) 0.62432(12) 0.23936(15) 0.0297(5) Uani 1 1 d . . . . .
H3A H 0.3154 0.6220 0.1777 0.036 Uiso 1 1 calc R . . . .
H3B H 0.3349 0.6704 0.2605 0.036 Uiso 1 1 calc R . . . .
C4 C 0.1626(2) 0.61933(13) 0.25240(16) 0.0330(6) Uani 1 1 d . . . . .
H4A H 0.1482 0.6329 0.3117 0.040 Uiso 1 1 calc R . . . .
H4B H 0.1165 0.6530 0.2139 0.040 Uiso 1 1 calc R . . . .
C5 C 0.0396(2) 0.52121(14) 0.30721(16) 0.0369(6) Uani 1 1 d . . . . .
H5A H -0.0003 0.4759 0.2902 0.044 Uiso 1 1 calc R . . . .
H5B H -0.0287 0.5548 0.3179 0.044 Uiso 1 1 calc R . . . .
C6 C 0.1211(3) 0.51076(15) 0.38870(16) 0.0414(7) Uani 1 1 d . . . . .
H6A H 0.1440 0.5573 0.4130 0.050 Uiso 1 1 calc R . . . .
H6B H 0.0711 0.4859 0.4302 0.050 Uiso 1 1 calc R . . . .
C7 C 0.3497(3) 0.50554(16) 0.42029(16) 0.0429(7) Uani 1 1 d . . . . .
H7A H 0.4242 0.4744 0.4189 0.051 Uiso 1 1 calc R . . . .
H7B H 0.3338 0.5141 0.4806 0.051 Uiso 1 1 calc R . . . .
C8 C 0.3778(3) 0.57502(14) 0.37766(15) 0.0361(6) Uani 1 1 d . . . . .
H8A H 0.3135 0.6100 0.3916 0.043 Uiso 1 1 calc R . . . .
H8B H 0.4612 0.5924 0.4004 0.043 Uiso 1 1 calc R . . . .
C9 C 0.5097(2) 0.56767(13) 0.25331(16) 0.0314(5) Uani 1 1 d . . . . .
H9 H 0.5010 0.5575 0.1909 0.038 Uiso 1 1 calc R . . . .
C10 C 0.5896(3) 0.50874(14) 0.29426(18) 0.0414(6) Uani 1 1 d . . . . .
H10A H 0.6112 0.5200 0.3542 0.062 Uiso 1 1 calc GR . . . .
H10B H 0.6671 0.5036 0.2645 0.062 Uiso 1 1 calc GR . . . .
H10C H 0.5419 0.4647 0.2904 0.062 Uiso 1 1 calc GR . . . .
C11 C 0.5786(3) 0.63807(14) 0.26356(17) 0.0375(6) Uani 1 1 d . . . . .
H11A H 0.5286 0.6747 0.2334 0.056 Uiso 1 1 calc GR . . . .
H11B H 0.6612 0.6345 0.2397 0.056 Uiso 1 1 calc GR . . . .
H11C H 0.5901 0.6500 0.3241 0.056 Uiso 1 1 calc GR . . . .
C12 C 0.0315(2) 0.54261(14) 0.15346(16) 0.0348(6) Uani 1 1 d . . . . .
H12 H 0.0065 0.4922 0.1468 0.042 Uiso 1 1 calc R . . . .
C13 C 0.1086(2) 0.56035(14) 0.07851(16) 0.0362(6) Uani 1 1 d . . . . .
H13A H 0.1322 0.6100 0.0810 0.054 Uiso 1 1 calc GR . . . .
H13B H 0.0584 0.5510 0.0252 0.054 Uiso 1 1 calc GR . . . .
H13C H 0.1851 0.5314 0.0810 0.054 Uiso 1 1 calc GR . . . .
C14 C -0.0912(3) 0.58502(16) 0.14997(19) 0.0461(7) Uani 1 1 d . . . . .
H14A H -0.0714 0.6352 0.1513 0.069 Uiso 1 1 calc GR . . . .
H14B H -0.1390 0.5730 0.1991 0.069 Uiso 1 1 calc GR . . . .
H14C H -0.1418 0.5739 0.0973 0.069 Uiso 1 1 calc GR . . . .
C15 C 0.2247(3) 0.39634(16) 0.40933(18) 0.0485(7) Uani 1 1 d . . . . .
H15 H 0.1439 0.3776 0.3820 0.058 Uiso 1 1 calc R . . . .
C16 C 0.3294(3) 0.34895(16) 0.3830(2) 0.0604(9) Uani 1 1 d . . . . .
H16A H 0.3409 0.3555 0.3223 0.091 Uiso 1 1 calc GR . . . .
H16B H 0.3072 0.3000 0.3935 0.091 Uiso 1 1 calc GR . . . .
H16C H 0.4079 0.3607 0.4162 0.091 Uiso 1 1 calc GR . . . .
C17 C 0.2150(4) 0.3922(2) 0.5060(2) 0.0751(12) Uani 1 1 d . . . . .
H17A H 0.2972 0.4031 0.5350 0.113 Uiso 1 1 calc GR . . . .
H17B H 0.1895 0.3447 0.5215 0.113 Uiso 1 1 calc GR . . . .
H17C H 0.1521 0.4260 0.5232 0.113 Uiso 1 1 calc GR . . . .
C18 C 0.5138(2) 0.36987(13) 0.06131(16) 0.0347(6) Uani 1 1 d . . . . .
C19 C 0.6340(3) 0.41010(17) 0.0501(3) 0.0632(10) Uani 1 1 d . . . . .
H19A H 0.6137 0.4547 0.0214 0.095 Uiso 1 1 calc GR . . . .
H19B H 0.6892 0.3824 0.0156 0.095 Uiso 1 1 calc GR . . . .
H19C H 0.6771 0.4193 0.1060 0.095 Uiso 1 1 calc GR . . . .
C20 C 0.4461(3) 0.35506(19) -0.02531(18) 0.0568(8) Uani 1 1 d . . . . .
H20A H 0.3669 0.3303 -0.0175 0.085 Uiso 1 1 calc GR . . . .
H20B H 0.5000 0.3259 -0.0591 0.085 Uiso 1 1 calc GR . . . .
H20C H 0.4279 0.3995 -0.0550 0.085 Uiso 1 1 calc GR . . . .
C21 C 0.5378(3) 0.30290(15) 0.1116(2) 0.0519(8) Uani 1 1 d . . . . .
H21A H 0.5799 0.3142 0.1672 0.078 Uiso 1 1 calc GR . . . .
H21B H 0.5918 0.2717 0.0804 0.078 Uiso 1 1 calc GR . . . .
H21C H 0.4574 0.2795 0.1196 0.078 Uiso 1 1 calc GR . . . .
C22 C 0.0467(2) 0.29027(13) 0.13372(15) 0.0314(5) Uani 1 1 d . . . . .
C23 C 0.0841(3) 0.29304(18) 0.04227(17) 0.0496(7) Uani 1 1 d . . . . .
H23A H 0.0582 0.3382 0.0169 0.074 Uiso 1 1 calc GR . . . .
H23B H 0.0424 0.2548 0.0096 0.074 Uiso 1 1 calc GR . . . .
H23C H 0.1758 0.2879 0.0414 0.074 Uiso 1 1 calc GR . . . .
C24 C -0.0946(3) 0.29824(18) 0.1389(2) 0.0524(8) Uani 1 1 d . . . . .
H24A H -0.1148 0.2977 0.1987 0.079 Uiso 1 1 calc GR . . . .
H24B H -0.1380 0.2594 0.1086 0.079 Uiso 1 1 calc GR . . . .
H24C H -0.1222 0.3428 0.1128 0.079 Uiso 1 1 calc GR . . . .
C25 C 0.0954(3) 0.22487(14) 0.17820(19) 0.0439(7) Uani 1 1 d . . . . .
H25A H 0.1875 0.2232 0.1776 0.066 Uiso 1 1 calc GR . . . .
H25B H 0.0588 0.1836 0.1488 0.066 Uiso 1 1 calc GR . . . .
H25C H 0.0714 0.2252 0.2372 0.066 Uiso 1 1 calc GR . . . .
P1 P 0.21145(7) 0.67713(4) 0.59594(4) 0.03931(18) Uani 1 1 d . . . . .
F1 F 0.2503(3) 0.75262(12) 0.56469(15) 0.0932(8) Uani 1 1 d . . . . .
F2 F 0.13660(19) 0.66379(10) 0.50559(11) 0.0651(5) Uani 1 1 d . . . . .
F3 F 0.1672(2) 0.60386(13) 0.62708(18) 0.1036(9) Uani 1 1 d . . . . .
F4 F 0.28525(19) 0.69088(12) 0.68511(11) 0.0726(6) Uani 1 1 d . . . . .
F5 F 0.0878(2) 0.71223(14) 0.62883(12) 0.0835(7) Uani 1 1 d . . . . .
F6 F 0.33293(19) 0.64287(13) 0.56220(12) 0.0810(7) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ni1 N1 2.2044(19) . ?
Ni1 N2 2.195(2) . ?
Ni1 N3 2.198(2) . ?
Ni1 C1 1.854(3) . ?
Ni1 C2 1.933(3) . ?
N1 C3 1.482(3) . ?
N1 C8 1.490(3) . ?
N1 C9 1.507(3) . ?
N2 C4 1.484(3) . ?
N2 C5 1.487(3) . ?
N2 C12 1.503(3) . ?
N3 C6 1.492(4) . ?
N3 C7 1.477(3) . ?
N3 C15 1.508(3) . ?
N4 C1 1.166(3) . ?
N4 C18 1.462(3) . ?
N5 C2 1.151(3) . ?
N5 C22 1.448(3) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.524(3) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C6 1.512(4) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.524(4) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 H9 1.0000 . ?
C9 C10 1.525(4) . ?
C9 C11 1.532(3) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12 1.0000 . ?
C12 C13 1.520(3) . ?
C12 C14 1.532(4) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15 1.0000 . ?
C15 C16 1.512(5) . ?
C15 C17 1.535(4) . ?
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 C19 1.510(4) . ?
C18 C20 1.525(4) . ?
C18 C21 1.515(4) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 C23 1.521(4) . ?
C22 C24 1.517(3) . ?
C22 C25 1.504(4) . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
P1 F1 1.585(2) . ?
P1 F2 1.6026(18) . ?
P1 F3 1.563(2) . ?
P1 F4 1.5832(18) . ?
P1 F5 1.591(2) . ?
P1 F6 1.571(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
N2 Ni1 N1 82.86(7) . . ?
N2 Ni1 N3 83.79(8) . . ?
N3 Ni1 N1 80.77(7) . . ?
C1 Ni1 N1 97.81(9) . . ?
C1 Ni1 N2 133.44(10) . . ?
C1 Ni1 N3 142.55(10) . . ?
C1 Ni1 C2 87.63(11) . . ?
C2 Ni1 N1 174.34(9) . . ?
C2 Ni1 N2 92.29(10) . . ?
C2 Ni1 N3 95.85(9) . . ?
C3 N1 Ni1 101.16(14) . . ?
C3 N1 C8 111.32(19) . . ?
C3 N1 C9 109.59(18) . . ?
C8 N1 Ni1 109.87(14) . . ?
C8 N1 C9 112.23(19) . . ?
C9 N1 Ni1 112.17(14) . . ?
C4 N2 Ni1 107.87(15) . . ?
C4 N2 C5 112.47(19) . . ?
C4 N2 C12 113.1(2) . . ?
C5 N2 Ni1 100.58(15) . . ?
C5 N2 C12 110.10(19) . . ?
C12 N2 Ni1 112.03(14) . . ?
C6 N3 Ni1 106.33(15) . . ?
C6 N3 C15 109.9(2) . . ?
C7 N3 Ni1 105.31(15) . . ?
C7 N3 C6 111.1(2) . . ?
C7 N3 C15 111.6(2) . . ?
C15 N3 Ni1 112.46(17) . . ?
C1 N4 C18 166.7(3) . . ?
C2 N5 C22 175.5(3) . . ?
N4 C1 Ni1 169.8(2) . . ?
N5 C2 Ni1 168.5(2) . . ?
N1 C3 H3A 109.0 . . ?
N1 C3 H3B 109.0 . . ?
N1 C3 C4 113.07(19) . . ?
H3A C3 H3B 107.8 . . ?
C4 C3 H3A 109.0 . . ?
C4 C3 H3B 109.0 . . ?
N2 C4 C3 112.79(19) . . ?
N2 C4 H4A 109.0 . . ?
N2 C4 H4B 109.0 . . ?
C3 C4 H4A 109.0 . . ?
C3 C4 H4B 109.0 . . ?
H4A C4 H4B 107.8 . . ?
N2 C5 H5A 108.9 . . ?
N2 C5 H5B 108.9 . . ?
N2 C5 C6 113.2(2) . . ?
H5A C5 H5B 107.7 . . ?
C6 C5 H5A 108.9 . . ?
C6 C5 H5B 108.9 . . ?
N3 C6 C5 113.9(2) . . ?
N3 C6 H6A 108.8 . . ?
N3 C6 H6B 108.8 . . ?
C5 C6 H6A 108.8 . . ?
C5 C6 H6B 108.8 . . ?
H6A C6 H6B 107.7 . . ?
N3 C7 H7A 109.3 . . ?
N3 C7 H7B 109.3 . . ?
N3 C7 C8 111.6(2) . . ?
H7A C7 H7B 108.0 . . ?
C8 C7 H7A 109.3 . . ?
C8 C7 H7B 109.3 . . ?
N1 C8 C7 111.9(2) . . ?
N1 C8 H8A 109.2 . . ?
N1 C8 H8B 109.2 . . ?
C7 C8 H8A 109.2 . . ?
C7 C8 H8B 109.2 . . ?
H8A C8 H8B 107.9 . . ?
N1 C9 H9 106.5 . . ?
N1 C9 C10 111.8(2) . . ?
N1 C9 C11 114.3(2) . . ?
C10 C9 H9 106.5 . . ?
C10 C9 C11 110.6(2) . . ?
C11 C9 H9 106.5 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C9 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
C9 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N2 C12 H12 106.5 . . ?
N2 C12 C13 110.7(2) . . ?
N2 C12 C14 115.0(2) . . ?
C13 C12 H12 106.5 . . ?
C13 C12 C14 110.9(2) . . ?
C14 C12 H12 106.5 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C12 C14 H14A 109.5 . . ?
C12 C14 H14B 109.5 . . ?
C12 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N3 C15 H15 107.1 . . ?
N3 C15 C16 112.0(2) . . ?
N3 C15 C17 113.2(3) . . ?
C16 C15 H15 107.1 . . ?
C16 C15 C17 109.9(3) . . ?
C17 C15 H15 107.1 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C15 C17 H17A 109.5 . . ?
C15 C17 H17B 109.5 . . ?
C15 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
N4 C18 C19 107.4(2) . . ?
N4 C18 C20 108.1(2) . . ?
N4 C18 C21 107.9(2) . . ?
C19 C18 C20 109.9(3) . . ?
C19 C18 C21 112.0(2) . . ?
C21 C18 C20 111.4(3) . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C18 C20 H20A 109.5 . . ?
C18 C20 H20B 109.5 . . ?
C18 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C18 C21 H21A 109.5 . . ?
C18 C21 H21B 109.5 . . ?
C18 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
N5 C22 C23 107.1(2) . . ?
N5 C22 C24 107.9(2) . . ?
N5 C22 C25 106.7(2) . . ?
C24 C22 C23 111.8(2) . . ?
C25 C22 C23 111.5(2) . . ?
C25 C22 C24 111.6(2) . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C22 C24 H24A 109.5 . . ?
C22 C24 H24B 109.5 . . ?
C22 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C22 C25 H25A 109.5 . . ?
C22 C25 H25B 109.5 . . ?
C22 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
F1 P1 F2 89.56(12) . . ?
F1 P1 F5 87.55(15) . . ?
F3 P1 F1 177.53(16) . . ?
F3 P1 F2 89.72(13) . . ?
F3 P1 F4 90.63(14) . . ?
F3 P1 F5 90.08(15) . . ?
F3 P1 F6 90.34(15) . . ?
F4 P1 F1 90.08(13) . . ?
F4 P1 F2 179.60(12) . . ?
F4 P1 F5 90.67(11) . . ?
F5 P1 F2 89.13(11) . . ?
F6 P1 F1 92.03(15) . . ?
F6 P1 F2 90.20(11) . . ?
F6 P1 F4 90.00(11) . . ?
F6 P1 F5 179.21(12) . . ?

_olex2_exptl_crystal_mounting_method 
'mounted using Paratone-N oil to a 0.3 mm cryo-loop (Hampton Research) with the (0 1 -1) scattering planes roughly normal to the spindle axis'
_olex2_submission_special_instructions 'No special instructions were received'
_chemical_properties_physical    Air-sensitive,Moisture-sensitive
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_161_a
_database_code_depnum_ccdc_archive 'CCDC 2167418'
loop_
_audit_author_name
_audit_author_address
'Liviu Mirica'
;University of Illinois at Urbana Champaign
United States of America
;
_audit_update_record             
;
2022-04-16 deposited with the CCDC.	2022-06-09 downloaded from the CCDC.
;
_audit_creation_date             2022-04-14
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelxl_version_number           2014/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '1(C15 H33 N4 Ni1 O1), B1 F4'
_chemical_formula_sum            'C15 H33 B F4 N4 Ni O'
_chemical_formula_weight         430.97
_chemical_absolute_configuration ?
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      trigonal
_space_group_IT_number           161
_space_group_name_H-M_alt        'R 3 c'
_space_group_name_Hall           'R 3 -2"c'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'-y, -x, z+1/2'
'-x+y, y, z+1/2'
'x, x-y, z+1/2'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'-y+2/3, -x+1/3, z+5/6'
'-x+y+2/3, y+1/3, z+5/6'
'x+2/3, x-y+1/3, z+5/6'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'-y+1/3, -x+2/3, z+7/6'
'-x+y+1/3, y+2/3, z+7/6'
'x+1/3, x-y+2/3, z+7/6'

_cell_length_a                   22.2530(4)
_cell_length_b                   22.2530(4)
_cell_length_c                   27.3228(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     11717.4(5)
_cell_formula_units_Z            23.99994
_cell_measurement_reflns_used    38581
_cell_measurement_temperature    99.99
_cell_measurement_theta_max      28.291
_cell_measurement_theta_min      2.587
_shelx_estimated_absorpt_T_max   0.838
_shelx_estimated_absorpt_T_min   0.666
_exptl_absorpt_coefficient_mu    1.042
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6712
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0863 before and 0.0472 after correction. The Ratio of minimum to maximum transmission is 0.9001. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            purple
_exptl_crystal_density_diffrn    1.466
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             5472
_exptl_crystal_preparation       ?
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Acetonitrile, Diethylether'
_exptl_crystal_size_max          0.425
_exptl_crystal_size_mid          0.254
_exptl_crystal_size_min          0.176
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0367
_diffrn_reflns_av_unetI/netI     0.0164
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            72926
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.311
_diffrn_reflns_theta_min         2.587
_diffrn_ambient_temperature      99.99
_diffrn_detector                 'Bruker D8 Venture'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            'CPAD area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'kappa diffractometer'
_diffrn_measurement_device_type  'Bruker Kappa/ApexII CCD'
_diffrn_measurement_method       'profile data from φ and ω scans'
_diffrn_radiation_monochromator  multi-mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_target            Mo
_diffrn_source_type              'Ius microfocus sealed tube'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.994
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.997
_reflns_number_gt                6297
_reflns_number_total             6490
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.354
_refine_diff_density_min         -0.391
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details 
;
 Flack x determined using 3071 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.007(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     367
_refine_ls_number_reflns         6490
_refine_ls_number_restraints     188
_refine_ls_R_factor_all          0.0232
_refine_ls_R_factor_gt           0.0216
_refine_ls_restrained_S_all      1.064
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0285P)²+12.0472P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0532
_refine_ls_wR_factor_ref         0.0544
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 F3-B1 \\sim F5-B2 \\sim F7-B2 \\sim F1-B1 \\sim F8-B2 \\sim F4-B1 \\sim F6-B2
\\sim F2-B1
 with sigma of 0.01
 F2-F3 \\sim F2-F4 \\sim F2-F1 \\sim F3-F4 \\sim F3-F1 \\sim F4-F1
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
F1 \\sim F2 \\sim F3 \\sim F4 \\sim B1 \\sim F5 \\sim F6 \\sim F7 \\sim F8
\\sim B2: within 2A with sigma of 0.01 and sigma for terminal atoms of 0.02
4. Others
 Sof(F5)=Sof(F6)=Sof(F7)=Sof(F8)=Sof(B2)=1-FVAR(1)
 Sof(F1)=Sof(F2)=Sof(F3)=Sof(F4)=Sof(B1)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C3(H3), C12(H12), C15(H15), C18(H18)
5.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B), C6(H6A,H6B), C7(H7A,H7B), C8(H8A,H8B), C9(H9A,H9B),
 C10(H10A,H10B), C11(H11A,H11B)
5.c Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C), C5(H5A,H5B,H5C), C13(H13A,H13B,H13C), C14(H14A,H14B,H14C),
 C16(H16A,H16B,H16C), C17(H17A,H17B,H17C), C19(H19A,H19B,H19C), C20(H20A,H20B,
 H20C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Ni1 Ni 0.6667 0.3333 0.40314(2) 0.01568(10) Uani 1 3 d S T P . .
O1 O 0.6667 0.3333 0.50561(11) 0.0261(6) Uani 1 3 d S T P . .
N1 N 0.58962(11) 0.32484(11) 0.35804(7) 0.0211(4) Uani 1 1 d . . . . .
N2 N 0.6667 0.3333 0.46452(13) 0.0182(6) Uani 1 3 d S T P . .
C1 C 0.61975(14) 0.39544(13) 0.33653(9) 0.0265(5) Uani 1 1 d . . . . .
H1A H 0.6189 0.4276 0.3612 0.032 Uiso 1 1 calc R . . . .
H1B H 0.5912 0.3941 0.3083 0.032 Uiso 1 1 calc R . . . .
C2 C 0.57783(14) 0.27199(14) 0.31974(9) 0.0275(5) Uani 1 1 d . . . . .
H2A H 0.6019 0.2959 0.2892 0.033 Uiso 1 1 calc R . . . .
H2B H 0.5276 0.2440 0.3126 0.033 Uiso 1 1 calc R . . . .
C3 C 0.52498(13) 0.30774(14) 0.38636(9) 0.0248(5) Uani 1 1 d . . . . .
H3 H 0.5392 0.3439 0.4125 0.030 Uiso 1 1 calc R . . . .
C4 C 0.49551(13) 0.23825(14) 0.41252(10) 0.0295(5) Uani 1 1 d . . . . .
H4A H 0.4785 0.2008 0.3883 0.044 Uiso 1 1 calc GR . . . .
H4B H 0.4571 0.2315 0.4337 0.044 Uiso 1 1 calc GR . . . .
H4C H 0.5319 0.2377 0.4324 0.044 Uiso 1 1 calc GR . . . .
C5 C 0.46915(15) 0.31126(17) 0.35610(11) 0.0351(6) Uani 1 1 d . . . . .
H5A H 0.4868 0.3588 0.3445 0.053 Uiso 1 1 calc GR . . . .
H5B H 0.4279 0.2973 0.3764 0.053 Uiso 1 1 calc GR . . . .
H5C H 0.4568 0.2799 0.3280 0.053 Uiso 1 1 calc GR . . . .
Ni2 Ni 0.62428(2) 0.84084(2) 0.41492(2) 0.01586(6) Uani 1 1 d . . . . .
O2 O 0.67222(10) 0.75037(10) 0.44070(8) 0.0325(4) Uani 1 1 d . . . . .
N3 N 0.56703(10) 0.85879(11) 0.46542(7) 0.0203(4) Uani 1 1 d . . . . .
N4 N 0.66507(10) 0.94278(10) 0.39350(7) 0.0186(4) Uani 1 1 d . . . . .
N5 N 0.54636(10) 0.81748(10) 0.36562(7) 0.0167(3) Uani 1 1 d . . . . .
N6 N 0.65724(10) 0.79104(10) 0.42816(7) 0.0191(4) Uani 1 1 d . . . . .
C6 C 0.58820(13) 0.93397(12) 0.46284(9) 0.0231(5) Uani 1 1 d . . . . .
H6A H 0.5896 0.9517 0.4963 0.028 Uiso 1 1 calc R . . . .
H6B H 0.5532 0.9392 0.4438 0.028 Uiso 1 1 calc R . . . .
C7 C 0.65893(12) 0.97671(12) 0.43896(9) 0.0227(5) Uani 1 1 d . . . . .
H7A H 0.6663 1.0233 0.4307 0.027 Uiso 1 1 calc R . . . .
H7B H 0.6955 0.9828 0.4624 0.027 Uiso 1 1 calc R . . . .
C8 C 0.61860(12) 0.94491(12) 0.35436(9) 0.0220(4) Uani 1 1 d . . . . .
H8A H 0.6471 0.9808 0.3299 0.026 Uiso 1 1 calc R . . . .
H8B H 0.5860 0.9578 0.3692 0.026 Uiso 1 1 calc R . . . .
C9 C 0.57776(12) 0.87491(12) 0.32907(8) 0.0227(5) Uani 1 1 d . . . . .
H9A H 0.5406 0.8744 0.3089 0.027 Uiso 1 1 calc R . . . .
H9B H 0.6090 0.8677 0.3071 0.027 Uiso 1 1 calc R . . . .
C10 C 0.48959(11) 0.82104(12) 0.39277(9) 0.0209(4) Uani 1 1 d . . . . .
H10A H 0.4441 0.7836 0.3810 0.025 Uiso 1 1 calc R . . . .
H10B H 0.4923 0.8660 0.3857 0.025 Uiso 1 1 calc R . . . .
C11 C 0.49458(12) 0.81378(13) 0.44782(9) 0.0238(5) Uani 1 1 d . . . . .
H11A H 0.4634 0.8268 0.4648 0.029 Uiso 1 1 calc R . . . .
H11B H 0.4791 0.7648 0.4559 0.029 Uiso 1 1 calc R . . . .
C12 C 0.57522(15) 0.83566(14) 0.51572(9) 0.0303(6) Uani 1 1 d . . . . .
H12 H 0.5656 0.7869 0.5125 0.036 Uiso 1 1 calc R . . . .
C13 C 0.52349(19) 0.83467(17) 0.55268(11) 0.0442(8) Uani 1 1 d . . . . .
H13A H 0.5267 0.8802 0.5533 0.066 Uiso 1 1 calc GR . . . .
H13B H 0.5341 0.8240 0.5852 0.066 Uiso 1 1 calc GR . . . .
H13C H 0.4764 0.7992 0.5433 0.066 Uiso 1 1 calc GR . . . .
C14 C 0.64962(17) 0.87912(17) 0.53449(10) 0.0376(6) Uani 1 1 d . . . . .
H14A H 0.6819 0.8797 0.5099 0.056 Uiso 1 1 calc GR . . . .
H14B H 0.6548 0.8588 0.5649 0.056 Uiso 1 1 calc GR . . . .
H14C H 0.6598 0.9267 0.5407 0.056 Uiso 1 1 calc GR . . . .
C15 C 0.73932(12) 0.97931(12) 0.37565(9) 0.0217(4) Uani 1 1 d . . . . .
H15 H 0.7530 1.0283 0.3675 0.026 Uiso 1 1 calc R . . . .
C16 C 0.78879(13) 0.98064(14) 0.41461(9) 0.0270(5) Uani 1 1 d . . . . .
H16A H 0.7924 1.0119 0.4411 0.040 Uiso 1 1 calc GR . . . .
H16B H 0.8347 0.9971 0.4001 0.040 Uiso 1 1 calc GR . . . .
H16C H 0.7711 0.9338 0.4277 0.040 Uiso 1 1 calc GR . . . .
C17 C 0.74684(13) 0.94502(15) 0.32947(9) 0.0275(5) Uani 1 1 d . . . . .
H17A H 0.7317 0.8963 0.3363 0.041 Uiso 1 1 calc GR . . . .
H17B H 0.7955 0.9691 0.3191 0.041 Uiso 1 1 calc GR . . . .
H17C H 0.7181 0.9477 0.3034 0.041 Uiso 1 1 calc GR . . . .
C18 C 0.51876(12) 0.74805(12) 0.34086(8) 0.0193(4) Uani 1 1 d . . . . .
H18 H 0.4820 0.7424 0.3172 0.023 Uiso 1 1 calc R . . . .
C19 C 0.48600(13) 0.68866(12) 0.37744(9) 0.0233(5) Uani 1 1 d . . . . .
H19A H 0.5209 0.6937 0.4015 0.035 Uiso 1 1 calc GR . . . .
H19B H 0.4685 0.6444 0.3602 0.035 Uiso 1 1 calc GR . . . .
H19C H 0.4475 0.6896 0.3942 0.035 Uiso 1 1 calc GR . . . .
C20 C 0.57556(13) 0.74373(14) 0.31205(9) 0.0257(5) Uani 1 1 d . . . . .
H20A H 0.5867 0.7722 0.2824 0.038 Uiso 1 1 calc GR . . . .
H20B H 0.5591 0.6954 0.3029 0.038 Uiso 1 1 calc GR . . . .
H20C H 0.6172 0.7608 0.3324 0.038 Uiso 1 1 calc GR . . . .
F1 F 0.4917(11) 0.5151(13) 0.3902(8) 0.042(5) Uani 0.301(6) 1 d D U . A 1
F2 F 0.5448(6) 0.5824(6) 0.3245(5) 0.066(3) Uani 0.301(6) 1 d D U . A 1
F3 F 0.5146(6) 0.4719(5) 0.3242(4) 0.084(3) Uani 0.301(6) 1 d D U . A 1
F4 F 0.6014(4) 0.5456(7) 0.3708(4) 0.079(4) Uani 0.301(6) 1 d D U . A 1
B1 B 0.5382(6) 0.5297(6) 0.3532(5) 0.038(4) Uani 0.301(6) 1 d D U . A 1
F5 F 0.4899(5) 0.5206(6) 0.3873(4) 0.045(2) Uani 0.699(6) 1 d D U . A 2
F6 F 0.59641(15) 0.61170(16) 0.37374(11) 0.0560(10) Uani 0.699(6) 1 d D U . A 2
F7 F 0.5315(3) 0.5531(3) 0.31059(15) 0.0691(16) Uani 0.699(6) 1 d D U . A 2
F8 F 0.5778(3) 0.5064(3) 0.3617(2) 0.0846(18) Uani 0.699(6) 1 d D U . A 2
B2 B 0.5476(3) 0.5459(3) 0.3575(2) 0.0251(11) Uani 0.699(6) 1 d D U . A 2
F9 F 0.6667 0.3333 0.62222(11) 0.0463(8) Uani 1 3 d S T P . .
F10 F 0.60640(10) 0.33064(11) 0.68905(8) 0.0468(5) Uani 1 1 d . . . . .
B3 B 0.6667 0.3333 0.67239(16) 0.0206(9) Uani 1 3 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 N1 2.042(2) . ?
Ni1 N1 2.042(2) 3_665 ?
Ni1 N1 2.042(2) 2_655 ?
Ni1 N2 1.677(4) . ?
O1 N2 1.123(5) . ?
N1 C1 1.487(3) . ?
N1 C2 1.496(3) . ?
N1 C3 1.505(3) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C1 C2 1.523(4) 3_665 ?
C2 C1 1.523(4) 2_655 ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 H3 1.0000 . ?
C3 C4 1.522(4) . ?
C3 C5 1.527(3) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
Ni2 N3 2.0481(19) . ?
Ni2 N4 2.062(2) . ?
Ni2 N5 2.0467(19) . ?
Ni2 N6 1.646(2) . ?
O2 N6 1.162(3) . ?
N3 C6 1.496(3) . ?
N3 C11 1.490(3) . ?
N3 C12 1.510(3) . ?
N4 C7 1.495(3) . ?
N4 C8 1.505(3) . ?
N4 C15 1.512(3) . ?
N5 C9 1.492(3) . ?
N5 C10 1.501(3) . ?
N5 C18 1.508(3) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 C7 1.520(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.521(3) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.523(3) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 H12 1.0000 . ?
C12 C13 1.523(4) . ?
C12 C14 1.529(4) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15 1.0000 . ?
C15 C16 1.521(3) . ?
C15 C17 1.527(4) . ?
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 H18 1.0000 . ?
C18 C19 1.521(3) . ?
C18 C20 1.532(3) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
F1 B1 1.364(10) . ?
F2 B1 1.356(10) . ?
F3 B1 1.372(10) . ?
F4 B1 1.355(10) . ?
F5 B2 1.379(6) . ?
F6 B2 1.389(6) . ?
F7 B2 1.363(6) . ?
F8 B2 1.354(6) . ?
F9 B3 1.371(5) . ?
F10 B3 1.389(2) . ?
B3 F10 1.389(2) 2_655 ?
B3 F10 1.389(2) 3_665 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 Ni1 N1 87.35(8) 2_655 3_665 ?
N1 Ni1 N1 87.35(8) 2_655 . ?
N1 Ni1 N1 87.35(8) 3_665 . ?
N2 Ni1 N1 127.12(6) . . ?
N2 Ni1 N1 127.12(6) . 2_655 ?
N2 Ni1 N1 127.12(6) . 3_665 ?
C1 N1 Ni1 103.10(14) . . ?
C1 N1 C2 111.30(19) . . ?
C1 N1 C3 109.85(19) . . ?
C2 N1 Ni1 107.69(15) . . ?
C2 N1 C3 113.01(19) . . ?
C3 N1 Ni1 111.42(14) . . ?
O1 N2 Ni1 180.0 . . ?
N1 C1 H1A 109.4 . . ?
N1 C1 H1B 109.4 . . ?
N1 C1 C2 111.1(2) . 3_665 ?
H1A C1 H1B 108.0 . . ?
C2 C1 H1A 109.4 3_665 . ?
C2 C1 H1B 109.4 3_665 . ?
N1 C2 C1 111.15(19) . 2_655 ?
N1 C2 H2A 109.4 . . ?
N1 C2 H2B 109.4 . . ?
C1 C2 H2A 109.4 2_655 . ?
C1 C2 H2B 109.4 2_655 . ?
H2A C2 H2B 108.0 . . ?
N1 C3 H3 106.5 . . ?
N1 C3 C4 111.7(2) . . ?
N1 C3 C5 114.1(2) . . ?
C4 C3 H3 106.5 . . ?
C4 C3 C5 111.0(2) . . ?
C5 C3 H3 106.5 . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C3 C5 H5A 109.5 . . ?
C3 C5 H5B 109.5 . . ?
C3 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
N3 Ni2 N4 87.21(8) . . ?
N5 Ni2 N3 87.84(7) . . ?
N5 Ni2 N4 86.78(7) . . ?
N6 Ni2 N3 120.88(9) . . ?
N6 Ni2 N4 134.72(9) . . ?
N6 Ni2 N5 125.42(9) . . ?
C6 N3 Ni2 107.91(14) . . ?
C6 N3 C12 113.56(19) . . ?
C11 N3 Ni2 102.77(13) . . ?
C11 N3 C6 111.51(19) . . ?
C11 N3 C12 109.8(2) . . ?
C12 N3 Ni2 110.72(16) . . ?
C7 N4 Ni2 102.63(14) . . ?
C7 N4 C8 109.69(18) . . ?
C7 N4 C15 110.35(18) . . ?
C8 N4 Ni2 107.75(14) . . ?
C8 N4 C15 109.72(17) . . ?
C15 N4 Ni2 116.40(14) . . ?
C9 N5 Ni2 104.39(13) . . ?
C9 N5 C10 109.36(18) . . ?
C9 N5 C18 110.72(17) . . ?
C10 N5 Ni2 106.85(13) . . ?
C10 N5 C18 110.70(17) . . ?
C18 N5 Ni2 114.52(13) . . ?
O2 N6 Ni2 170.9(2) . . ?
N3 C6 H6A 109.3 . . ?
N3 C6 H6B 109.3 . . ?
N3 C6 C7 111.62(19) . . ?
H6A C6 H6B 108.0 . . ?
C7 C6 H6A 109.3 . . ?
C7 C6 H6B 109.3 . . ?
N4 C7 C6 111.60(19) . . ?
N4 C7 H7A 109.3 . . ?
N4 C7 H7B 109.3 . . ?
C6 C7 H7A 109.3 . . ?
C6 C7 H7B 109.3 . . ?
H7A C7 H7B 108.0 . . ?
N4 C8 H8A 109.4 . . ?
N4 C8 H8B 109.4 . . ?
N4 C8 C9 111.03(19) . . ?
H8A C8 H8B 108.0 . . ?
C9 C8 H8A 109.4 . . ?
C9 C8 H8B 109.4 . . ?
N5 C9 C8 110.94(18) . . ?
N5 C9 H9A 109.5 . . ?
N5 C9 H9B 109.5 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 108.0 . . ?
N5 C10 H10A 109.2 . . ?
N5 C10 H10B 109.2 . . ?
N5 C10 C11 112.00(18) . . ?
H10A C10 H10B 107.9 . . ?
C11 C10 H10A 109.2 . . ?
C11 C10 H10B 109.2 . . ?
N3 C11 C10 111.06(18) . . ?
N3 C11 H11A 109.4 . . ?
N3 C11 H11B 109.4 . . ?
C10 C11 H11A 109.4 . . ?
C10 C11 H11B 109.4 . . ?
H11A C11 H11B 108.0 . . ?
N3 C12 H12 107.0 . . ?
N3 C12 C13 112.9(2) . . ?
N3 C12 C14 111.5(2) . . ?
C13 C12 H12 107.0 . . ?
C13 C12 C14 111.0(2) . . ?
C14 C12 H12 107.0 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C12 C14 H14A 109.5 . . ?
C12 C14 H14B 109.5 . . ?
C12 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N4 C15 H15 108.2 . . ?
N4 C15 C16 111.75(19) . . ?
N4 C15 C17 111.18(19) . . ?
C16 C15 H15 108.2 . . ?
C16 C15 C17 109.2(2) . . ?
C17 C15 H15 108.2 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C15 C17 H17A 109.5 . . ?
C15 C17 H17B 109.5 . . ?
C15 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
N5 C18 H18 108.0 . . ?
N5 C18 C19 111.61(18) . . ?
N5 C18 C20 111.63(18) . . ?
C19 C18 H18 108.0 . . ?
C19 C18 C20 109.6(2) . . ?
C20 C18 H18 108.0 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C18 C20 H20A 109.5 . . ?
C18 C20 H20B 109.5 . . ?
C18 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
F1 B1 F3 108.3(13) . . ?
F2 B1 F1 112.0(13) . . ?
F2 B1 F3 107.6(10) . . ?
F4 B1 F1 111.3(13) . . ?
F4 B1 F2 109.3(11) . . ?
F4 B1 F3 108.1(10) . . ?
F5 B2 F6 108.7(6) . . ?
F7 B2 F5 110.9(6) . . ?
F7 B2 F6 106.8(4) . . ?
F8 B2 F5 110.4(6) . . ?
F8 B2 F6 106.1(5) . . ?
F8 B2 F7 113.6(6) . . ?
F9 B3 F10 109.1(2) . 2_655 ?
F9 B3 F10 109.1(2) . 3_665 ?
F9 B3 F10 109.1(2) . . ?
F10 B3 F10 109.8(2) 2_655 . ?
F10 B3 F10 109.8(2) 3_665 . ?
F10 B3 F10 109.8(2) 2_655 3_665 ?

_olex2_exptl_crystal_mounting_method 'mounted with a spindle axis of (-1 0 -4)'
_olex2_submission_special_instructions 'No special instructions were received'
