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

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

data_tb060
_database_code_depnum_ccdc_archive 'CCDC 968465'
_audit_update_record             
;
2015-02-17 deposited with the CCDC.
2015-07-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            'Ni[k2-(CF2)4-](ItBu)[P(OiPr)3]2 '
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H41 F8 N2 Ni O3 P'
_chemical_formula_weight         647.27

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

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

_cell_length_a                   15.5474(12)
_cell_length_b                   9.9548(8)
_cell_length_c                   19.6379(15)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.862(4)
_cell_angle_gamma                90.00
_cell_volume                     3035.6(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    9866
_cell_measurement_theta_min      2.43
_cell_measurement_theta_max      28.40

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      n/a
_exptl_crystal_density_diffrn    1.416
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1352
_exptl_absorpt_coefficient_mu    0.768
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8805
_exptl_absorpt_correction_T_max  0.9271
_exptl_absorpt_process_details   'SADABS, Bruker (2003)'

_exptl_special_details           
; 
 Data collection is performed with three batch runs at phi = 0.00 deg 
 (650 frames), at phi = 120.00 deg (650 frames), and at phi = 240.00 deg 
 (650 frames). 
 Frame width = 0.30 deg in omega. 
 Data is merged, corrected for decay (if any), and treated with multi-scan 
 absorption corrections (if required). All symmetry-equivalent reflections 
 are merged for centrosymmetric data. 
 Friedel pairs are not merged for noncentrosymmetric data. 
;

_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            29150
_diffrn_reflns_av_R_equivalents  0.0226
_diffrn_reflns_av_sigmaI/netI    0.0215
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         2.08
_diffrn_reflns_theta_max         28.47
_reflns_number_total             7565
_reflns_number_gt                6509
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX II, Bruker (2009)'
_computing_cell_refinement       'APEX II, Bruker (2009)'
_computing_data_reduction        'XPREP, Bruker (2009)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXTL, Bruker (2004)'
_computing_publication_material  'SHELXTL, Bruker (2004)'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0478P)²+1.3213P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         7565
_refine_ls_number_parameters     352
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0399
_refine_ls_R_factor_gt           0.0326
_refine_ls_wR_factor_ref         0.0880
_refine_ls_wR_factor_gt          0.0838
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_restrained_S_all      1.011
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Ni1 Ni 0.248830(12) 0.010469(17) 0.469561(9) 0.01878(6) Uani 1 1 d . . .
P1 P 0.25514(3) -0.02745(4) 0.35878(2) 0.02455(9) Uani 1 1 d . . .
O1 O 0.27636(10) 0.09699(13) 0.31135(7) 0.0436(3) Uani 1 1 d . . .
O2 O 0.33532(9) -0.12169(14) 0.34828(7) 0.0416(3) Uani 1 1 d . . .
O3 O 0.17640(9) -0.08814(14) 0.31378(6) 0.0417(3) Uani 1 1 d . . .
N1 N 0.30899(8) 0.29244(12) 0.46353(7) 0.0267(3) Uani 1 1 d . . .
N2 N 0.17041(8) 0.28558(12) 0.45816(7) 0.0258(3) Uani 1 1 d . . .
C1 C 0.24405(11) 0.03415(16) 0.56815(8) 0.0282(3) Uani 1 1 d . . .
C2 C 0.27647(12) -0.09003(18) 0.60747(8) 0.0333(4) Uani 1 1 d . . .
C3 C 0.25013(12) -0.21065(16) 0.56478(9) 0.0327(4) Uani 1 1 d . . .
C4 C 0.26783(10) -0.17831(15) 0.49088(8) 0.0259(3) Uani 1 1 d . . .
F1 F 0.28749(10) 0.14176(11) 0.59781(6) 0.0532(3) Uani 1 1 d . . .
F2 F 0.16000(8) 0.05230(14) 0.58774(6) 0.0511(3) Uani 1 1 d . . .
F3 F 0.36373(7) -0.08705(13) 0.61351(6) 0.0476(3) Uani 1 1 d . . .
F4 F 0.24911(9) -0.09980(13) 0.67190(5) 0.0505(3) Uani 1 1 d . . .
F5 F 0.28683(10) -0.32502(11) 0.58923(6) 0.0556(3) Uani 1 1 d . . .
F6 F 0.16341(8) -0.22813(14) 0.56944(7) 0.0554(3) Uani 1 1 d . . .
F7 F 0.35386(7) -0.21256(11) 0.48508(6) 0.0425(3) Uani 1 1 d . . .
F8 F 0.22444(9) -0.27503(10) 0.45164(6) 0.0463(3) Uani 1 1 d . . .
C5 C 0.24145(9) 0.20473(14) 0.46019(7) 0.0215(3) Uani 1 1 d . . .
C6 C 0.27993(12) 0.42375(16) 0.46442(11) 0.0375(4) Uani 1 1 d . . .
H6A H 0.3147 0.5022 0.4668 0.045 Uiso 1 1 calc R . .
C7 C 0.19437(12) 0.41979(16) 0.46133(11) 0.0369(4) Uani 1 1 d . . .
H7A H 0.1566 0.4949 0.4613 0.044 Uiso 1 1 calc R . .
C8 C 0.40407(10) 0.26603(16) 0.46752(9) 0.0309(3) Uani 1 1 d . . .
C9 C 0.44292(14) 0.3320(2) 0.40601(13) 0.0512(5) Uani 1 1 d . . .
H9A H 0.4188 0.2903 0.3641 0.077 Uiso 1 1 calc R . .
H9B H 0.5056 0.3200 0.4089 0.077 Uiso 1 1 calc R . .
H9C H 0.4293 0.4281 0.4056 0.077 Uiso 1 1 calc R . .
C10 C 0.44134(14) 0.3302(3) 0.53377(12) 0.0530(5) Uani 1 1 d . . .
H10A H 0.4156 0.2878 0.5729 0.079 Uiso 1 1 calc R . .
H10B H 0.4283 0.4265 0.5335 0.079 Uiso 1 1 calc R . .
H10C H 0.5039 0.3173 0.5371 0.079 Uiso 1 1 calc R . .
C11 C 0.42520(12) 0.11836(18) 0.46708(13) 0.0454(5) Uani 1 1 d . . .
H11A H 0.4016 0.0779 0.4247 0.068 Uiso 1 1 calc R . .
H11B H 0.3999 0.0746 0.5061 0.068 Uiso 1 1 calc R . .
H11C H 0.4878 0.1065 0.4702 0.068 Uiso 1 1 calc R . .
C12 C 0.07691(10) 0.24953(17) 0.45336(9) 0.0284(3) Uani 1 1 d . . .
C13 C 0.03688(12) 0.2893(2) 0.52010(10) 0.0416(4) Uani 1 1 d . . .
H13A H 0.0644 0.2384 0.5579 0.062 Uiso 1 1 calc R . .
H13B H -0.0249 0.2695 0.5170 0.062 Uiso 1 1 calc R . .
H13C H 0.0455 0.3857 0.5282 0.062 Uiso 1 1 calc R . .
C14 C 0.03458(12) 0.3285(2) 0.39350(10) 0.0421(4) Uani 1 1 d . . .
H14A H 0.0603 0.3015 0.3511 0.063 Uiso 1 1 calc R . .
H14B H 0.0437 0.4248 0.4010 0.063 Uiso 1 1 calc R . .
H14C H -0.0273 0.3094 0.3903 0.063 Uiso 1 1 calc R . .
C15 C 0.06435(11) 0.10096(18) 0.43960(10) 0.0356(4) Uani 1 1 d . . .
H15A H 0.0897 0.0775 0.3965 0.053 Uiso 1 1 calc R . .
H15B H 0.0027 0.0802 0.4367 0.053 Uiso 1 1 calc R . .
H15C H 0.0926 0.0490 0.4767 0.053 Uiso 1 1 calc R . .
C16 C 0.21791(17) 0.1698(2) 0.26592(10) 0.0495(5) Uani 1 1 d . . .
H16A H 0.1585 0.1593 0.2824 0.059 Uiso 1 1 calc R . .
C17 C 0.24182(19) 0.3168(2) 0.27005(12) 0.0594(6) Uani 1 1 d . . .
H17A H 0.2399 0.3474 0.3174 0.089 Uiso 1 1 calc R . .
H17B H 0.2009 0.3692 0.2412 0.089 Uiso 1 1 calc R . .
H17C H 0.3001 0.3291 0.2542 0.089 Uiso 1 1 calc R . .
C18 C 0.2186(2) 0.1142(3) 0.19474(11) 0.0724(8) Uani 1 1 d . . .
H18A H 0.2022 0.0192 0.1952 0.109 Uiso 1 1 calc R . .
H18B H 0.2766 0.1231 0.1777 0.109 Uiso 1 1 calc R . .
H18C H 0.1776 0.1642 0.1649 0.109 Uiso 1 1 calc R . .
C19 C 0.36921(15) -0.1631(2) 0.28362(11) 0.0518(5) Uani 1 1 d . . .
H19A H 0.3237 -0.1535 0.2461 0.062 Uiso 1 1 calc R . .
C20 C 0.39337(19) -0.3089(3) 0.29247(14) 0.0711(8) Uani 1 1 d . . .
H20A H 0.3417 -0.3616 0.3008 0.107 Uiso 1 1 calc R . .
H20B H 0.4350 -0.3183 0.3313 0.107 Uiso 1 1 calc R . .
H20C H 0.4191 -0.3415 0.2510 0.107 Uiso 1 1 calc R . .
C21 C 0.4451(2) -0.0757(4) 0.2694(2) 0.1040(13) Uani 1 1 d . . .
H21A H 0.4261 0.0177 0.2640 0.156 Uiso 1 1 calc R . .
H21B H 0.4706 -0.1058 0.2274 0.156 Uiso 1 1 calc R . .
H21C H 0.4881 -0.0820 0.3075 0.156 Uiso 1 1 calc R . .
C22 C 0.10968(12) -0.1791(2) 0.33257(9) 0.0384(4) Uani 1 1 d . . .
H22A H 0.1041 -0.1766 0.3831 0.046 Uiso 1 1 calc R . .
C23 C 0.02740(17) -0.1293(3) 0.29692(13) 0.0705(8) Uani 1 1 d . . .
H23A H 0.0148 -0.0385 0.3128 0.106 Uiso 1 1 calc R . .
H23B H -0.0201 -0.1895 0.3072 0.106 Uiso 1 1 calc R . .
H23C H 0.0342 -0.1277 0.2476 0.106 Uiso 1 1 calc R . .
C24 C 0.1322(2) -0.3197(2) 0.31064(13) 0.0674(7) Uani 1 1 d . . .
H24A H 0.1859 -0.3481 0.3348 0.101 Uiso 1 1 calc R . .
H24B H 0.1398 -0.3209 0.2614 0.101 Uiso 1 1 calc R . .
H24C H 0.0857 -0.3813 0.3215 0.101 Uiso 1 1 calc R . .


_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 C5 1.9454(14) . ?
Ni1 C4 1.9447(15) . ?
Ni1 C1 1.9555(16) . ?
Ni1 P1 2.2150(5) . ?
P1 O2 1.5818(14) . ?
P1 O3 1.5926(13) . ?
P1 O1 1.5943(13) . ?
O1 C16 1.437(3) . ?
O2 C19 1.459(2) . ?
O3 C22 1.439(2) . ?
N1 C5 1.3647(19) . ?
N1 C6 1.383(2) . ?
N1 C8 1.500(2) . ?
N2 C5 1.3654(19) . ?
N2 C7 1.388(2) . ?
N2 C12 1.496(2) . ?
C1 F1 1.3798(19) . ?
C1 F2 1.392(2) . ?
C1 C2 1.530(2) . ?
C2 F3 1.356(2) . ?
C2 F4 1.358(2) . ?
C2 C3 1.509(2) . ?
C3 F5 1.3509(19) . ?
C3 F6 1.367(2) . ?
C3 C4 1.525(2) . ?
C4 F8 1.3871(18) . ?
C4 F7 1.3904(19) . ?
C6 C7 1.329(3) . ?
C8 C11 1.506(2) . ?
C8 C9 1.526(3) . ?
C8 C10 1.537(3) . ?
C12 C15 1.514(2) . ?
C12 C13 1.531(2) . ?
C12 C14 1.535(2) . ?
C16 C17 1.511(3) . ?
C16 C18 1.504(3) . ?
C19 C20 1.507(3) . ?
C19 C21 1.504(4) . ?
C22 C23 1.511(3) . ?
C22 C24 1.511(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 Ni1 C4 171.33(6) . . ?
C5 Ni1 C1 88.21(6) . . ?
C4 Ni1 C1 85.19(7) . . ?
C5 Ni1 P1 94.69(4) . . ?
C4 Ni1 P1 91.89(5) . . ?
C1 Ni1 P1 177.09(5) . . ?
O2 P1 O3 106.95(8) . . ?
O2 P1 O1 101.38(8) . . ?
O3 P1 O1 98.41(7) . . ?
O2 P1 Ni1 107.63(5) . . ?
O3 P1 Ni1 122.62(5) . . ?
O1 P1 Ni1 117.52(6) . . ?
C16 O1 P1 127.70(14) . . ?
C19 O2 P1 127.05(13) . . ?
C22 O3 P1 129.83(11) . . ?
C5 N1 C6 110.74(13) . . ?
C5 N1 C8 130.13(12) . . ?
C6 N1 C8 119.12(13) . . ?
C5 N2 C7 110.57(13) . . ?
C5 N2 C12 129.98(12) . . ?
C7 N2 C12 119.45(13) . . ?
F1 C1 F2 103.24(13) . . ?
F1 C1 C2 105.80(14) . . ?
F2 C1 C2 104.81(13) . . ?
F1 C1 Ni1 118.00(11) . . ?
F2 C1 Ni1 111.83(11) . . ?
C2 C1 Ni1 112.00(11) . . ?
F3 C2 F4 106.18(14) . . ?
F3 C2 C3 107.96(15) . . ?
F4 C2 C3 111.81(15) . . ?
F3 C2 C1 109.24(15) . . ?
F4 C2 C1 114.68(14) . . ?
C3 C2 C1 106.80(13) . . ?
F5 C3 F6 105.63(14) . . ?
F5 C3 C2 112.03(15) . . ?
F6 C3 C2 107.77(15) . . ?
F5 C3 C4 115.02(15) . . ?
F6 C3 C4 108.42(14) . . ?
C2 C3 C4 107.69(13) . . ?
F8 C4 F7 103.15(12) . . ?
F8 C4 C3 106.04(13) . . ?
F7 C4 C3 104.25(13) . . ?
F8 C4 Ni1 119.13(11) . . ?
F7 C4 Ni1 110.84(10) . . ?
C3 C4 Ni1 112.09(10) . . ?
N1 C5 N2 104.10(12) . . ?
N1 C5 Ni1 126.14(11) . . ?
N2 C5 Ni1 129.23(11) . . ?
C7 C6 N1 107.34(14) . . ?
C6 C7 N2 107.25(14) . . ?
N1 C8 C11 112.67(13) . . ?
N1 C8 C9 108.14(15) . . ?
C11 C8 C9 108.68(17) . . ?
N1 C8 C10 107.49(15) . . ?
C11 C8 C10 109.72(17) . . ?
C9 C8 C10 110.11(17) . . ?
N2 C12 C15 111.22(13) . . ?
N2 C12 C13 108.62(14) . . ?
C15 C12 C13 110.57(15) . . ?
N2 C12 C14 107.68(13) . . ?
C15 C12 C14 108.47(15) . . ?
C13 C12 C14 110.25(15) . . ?
O1 C16 C17 107.99(19) . . ?
O1 C16 C18 110.9(2) . . ?
C17 C16 C18 113.14(19) . . ?
O2 C19 C20 105.71(19) . . ?
O2 C19 C21 108.6(2) . . ?
C20 C19 C21 112.7(2) . . ?
O3 C22 C23 106.23(18) . . ?
O3 C22 C24 109.22(18) . . ?
C23 C22 C24 112.0(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 Ni1 P1 O2 128.84(7) . . . . ?
C4 Ni1 P1 O2 -45.52(8) . . . . ?
C1 Ni1 P1 O2 -47.3(10) . . . . ?
C5 Ni1 P1 O3 -106.64(8) . . . . ?
C4 Ni1 P1 O3 79.00(8) . . . . ?
C1 Ni1 P1 O3 77.2(10) . . . . ?
C5 Ni1 P1 O1 15.32(8) . . . . ?
C4 Ni1 P1 O1 -159.04(8) . . . . ?
C1 Ni1 P1 O1 -160.8(10) . . . . ?
O2 P1 O1 C16 137.90(17) . . . . ?
O3 P1 O1 C16 28.60(18) . . . . ?
Ni1 P1 O1 C16 -105.15(16) . . . . ?
O3 P1 O2 C19 52.48(18) . . . . ?
O1 P1 O2 C19 -50.07(18) . . . . ?
Ni1 P1 O2 C19 -174.03(16) . . . . ?
O2 P1 O3 C22 94.41(18) . . . . ?
O1 P1 O3 C22 -160.90(17) . . . . ?
Ni1 P1 O3 C22 -30.42(19) . . . . ?
C5 Ni1 C1 F1 -38.37(13) . . . . ?
C4 Ni1 C1 F1 136.00(14) . . . . ?
P1 Ni1 C1 F1 137.8(10) . . . . ?
C5 Ni1 C1 F2 81.13(12) . . . . ?
C4 Ni1 C1 F2 -104.51(12) . . . . ?
P1 Ni1 C1 F2 -102.7(10) . . . . ?
C5 Ni1 C1 C2 -161.56(13) . . . . ?
C4 Ni1 C1 C2 12.80(13) . . . . ?
P1 Ni1 C1 C2 14.6(11) . . . . ?
F1 C1 C2 F3 -47.83(17) . . . . ?
F2 C1 C2 F3 -156.55(14) . . . . ?
Ni1 C1 C2 F3 82.01(15) . . . . ?
F1 C1 C2 F4 71.20(19) . . . . ?
F2 C1 C2 F4 -37.5(2) . . . . ?
Ni1 C1 C2 F4 -158.97(12) . . . . ?
F1 C1 C2 C3 -164.34(14) . . . . ?
F2 C1 C2 C3 86.93(16) . . . . ?
Ni1 C1 C2 C3 -34.51(17) . . . . ?
F3 C2 C3 F5 52.96(19) . . . . ?
F4 C2 C3 F5 -63.5(2) . . . . ?
C1 C2 C3 F5 170.32(15) . . . . ?
F3 C2 C3 F6 168.74(13) . . . . ?
F4 C2 C3 F6 52.31(18) . . . . ?
C1 C2 C3 F6 -73.89(16) . . . . ?
F3 C2 C3 C4 -74.48(17) . . . . ?
F4 C2 C3 C4 169.08(14) . . . . ?
C1 C2 C3 C4 42.88(18) . . . . ?
F5 C3 C4 F8 68.49(19) . . . . ?
F6 C3 C4 F8 -49.47(17) . . . . ?
C2 C3 C4 F8 -165.83(13) . . . . ?
F5 C3 C4 F7 -40.01(18) . . . . ?
F6 C3 C4 F7 -157.97(13) . . . . ?
C2 C3 C4 F7 85.67(15) . . . . ?
F5 C3 C4 Ni1 -159.96(12) . . . . ?
F6 C3 C4 Ni1 82.08(15) . . . . ?
C2 C3 C4 Ni1 -34.28(17) . . . . ?
C5 Ni1 C4 F8 177.3(4) . . . . ?
C1 Ni1 C4 F8 136.64(13) . . . . ?
P1 Ni1 C4 F8 -43.26(12) . . . . ?
C5 Ni1 C4 F7 -63.3(5) . . . . ?
C1 Ni1 C4 F7 -103.96(11) . . . . ?
P1 Ni1 C4 F7 76.13(10) . . . . ?
C5 Ni1 C4 C3 52.7(5) . . . . ?
C1 Ni1 C4 C3 12.07(12) . . . . ?
P1 Ni1 C4 C3 -167.84(11) . . . . ?
C6 N1 C5 N2 0.77(18) . . . . ?
C8 N1 C5 N2 179.44(16) . . . . ?
C6 N1 C5 Ni1 -171.52(13) . . . . ?
C8 N1 C5 Ni1 7.2(2) . . . . ?
C7 N2 C5 N1 -0.96(18) . . . . ?
C12 N2 C5 N1 179.11(15) . . . . ?
C7 N2 C5 Ni1 170.99(13) . . . . ?
C12 N2 C5 Ni1 -8.9(2) . . . . ?
C4 Ni1 C5 N1 46.7(5) . . . . ?
C1 Ni1 C5 N1 87.23(14) . . . . ?
P1 Ni1 C5 N1 -92.58(13) . . . . ?
C4 Ni1 C5 N2 -123.6(4) . . . . ?
C1 Ni1 C5 N2 -83.09(15) . . . . ?
P1 Ni1 C5 N2 97.10(14) . . . . ?
C5 N1 C6 C7 -0.3(2) . . . . ?
C8 N1 C6 C7 -179.13(16) . . . . ?
N1 C6 C7 N2 -0.3(2) . . . . ?
C5 N2 C7 C6 0.8(2) . . . . ?
C12 N2 C7 C6 -179.24(16) . . . . ?
C5 N1 C8 C11 0.5(3) . . . . ?
C6 N1 C8 C11 179.11(18) . . . . ?
C5 N1 C8 C9 120.68(19) . . . . ?
C6 N1 C8 C9 -60.7(2) . . . . ?
C5 N1 C8 C10 -120.47(19) . . . . ?
C6 N1 C8 C10 58.1(2) . . . . ?
C5 N2 C12 C15 -8.8(2) . . . . ?
C7 N2 C12 C15 171.29(16) . . . . ?
C5 N2 C12 C13 113.13(18) . . . . ?
C7 N2 C12 C13 -66.8(2) . . . . ?
C5 N2 C12 C14 -127.49(18) . . . . ?
C7 N2 C12 C14 52.6(2) . . . . ?
P1 O1 C16 C17 141.61(17) . . . . ?
P1 O1 C16 C18 -93.9(2) . . . . ?
P1 O2 C19 C20 -139.78(18) . . . . ?
P1 O2 C19 C21 99.1(3) . . . . ?
P1 O3 C22 C23 139.82(17) . . . . ?
P1 O3 C22 C24 -99.2(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.985
_diffrn_reflns_theta_full        28.47
_diffrn_measured_fraction_theta_full 0.985
_refine_diff_density_max         0.944
_refine_diff_density_min         -0.261
_refine_diff_density_rms         0.053
####################################################################### 
# 
# 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_tb065
_database_code_depnum_ccdc_archive 'CCDC 968466'
_audit_update_record             
;
2015-02-17 deposited with the CCDC.
2015-07-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            '[Ni[k2-(CF2)4-](SIPr)] '
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C31 H38 F8 N2 Ni'
_chemical_formula_weight         649.34
_chemical_absolute_configuration ad

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

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   P2(1)2(1)2(1)

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

_cell_length_a                   10.8851(4)
_cell_length_b                   15.5440(6)
_cell_length_c                   18.9208(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3201.4(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    9846
_cell_measurement_theta_min      2.52
_cell_measurement_theta_max      28.14

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.07
_exptl_crystal_density_meas      n/a
_exptl_crystal_density_diffrn    1.347
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1352
_exptl_absorpt_coefficient_mu    0.675
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8713
_exptl_absorpt_correction_T_max  0.9543
_exptl_absorpt_process_details   'SADABS, Bruker (2003)'

_exptl_special_details           
; 
 Data collection is performed with three batch runs at phi = 0.00 deg 
 (650 frames), at phi = 120.00 deg (650 frames), and at phi = 240.00 deg 
 (650 frames). 
 Frame width = 0.30 deg in omega. 
 Data is merged, corrected for decay (if any), and treated with multi-scan 
 absorption corrections (if required). All symmetry-equivalent reflections 
 are merged for centrosymmetric data. 
 Friedel pairs are not merged for noncentrosymmetric data. 
;

_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            45918
_diffrn_reflns_av_R_equivalents  0.0281
_diffrn_reflns_av_sigmaI/netI    0.0229
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.15
_diffrn_reflns_theta_max         28.32
_reflns_number_total             7927
_reflns_number_gt                7204
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX II, Bruker (2009)'
_computing_cell_refinement       'APEX II, Bruker (2009)'
_computing_data_reduction        'XPREP, Bruker (2009)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXTL, Bruker (2004)'
_computing_publication_material  'SHELXTL, Bruker (2004)'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     'calc w=1/[σ²(Fo²)+(0.0428P)²]'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.144(7)
_refine_ls_number_reflns         7927
_refine_ls_number_parameters     380
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0318
_refine_ls_R_factor_gt           0.0266
_refine_ls_wR_factor_ref         0.0663
_refine_ls_wR_factor_gt          0.0643
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.035
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Ni1 Ni 0.838172(14) 0.504086(11) 0.979824(8) 0.02281(5) Uani 1 1 d . . .
N1 N 0.89653(12) 0.55873(8) 0.84091(6) 0.0229(2) Uani 1 1 d . . .
N2 N 0.90533(11) 0.41944(7) 0.84203(6) 0.0219(2) Uani 1 1 d . . .
F1 F 0.78193(12) 0.61791(7) 1.08603(6) 0.0503(3) Uani 1 1 d . . .
F2 F 0.66589(8) 0.50396(9) 1.09237(5) 0.0538(3) Uani 1 1 d . . .
F3 F 0.87105(11) 0.53465(8) 1.19317(5) 0.0539(3) Uani 1 1 d . . .
F4 F 0.83920(11) 0.41044(7) 1.14437(6) 0.0525(3) Uani 1 1 d . . .
F5 F 1.03790(10) 0.57515(7) 1.09405(6) 0.0494(3) Uani 1 1 d . . .
F6 F 1.07930(11) 0.44760(8) 1.13493(5) 0.0546(3) Uani 1 1 d . . .
F7 F 0.97711(10) 0.37206(6) 1.02463(5) 0.0414(2) Uani 1 1 d . . .
F8 F 1.08767(8) 0.47748(7) 0.98478(5) 0.0432(2) Uani 1 1 d . . .
C1 C 0.88803(11) 0.48918(9) 0.88211(6) 0.0208(2) Uani 1 1 d . . .
C2 C 0.91918(16) 0.53809(10) 0.76562(7) 0.0295(3) Uani 1 1 d . . .
H2A H 0.9997 0.5604 0.7497 0.035 Uiso 1 1 calc R . .
H2B H 0.8537 0.5617 0.7349 0.035 Uiso 1 1 calc R . .
C3 C 0.91732(16) 0.44026(10) 0.76596(7) 0.0291(3) Uani 1 1 d . . .
H3A H 0.8467 0.4178 0.7387 0.035 Uiso 1 1 calc R . .
H3B H 0.9943 0.4164 0.7461 0.035 Uiso 1 1 calc R . .
C4 C 0.89287(14) 0.64561(9) 0.86668(7) 0.0236(3) Uani 1 1 d . . .
C5 C 0.77808(17) 0.68418(11) 0.87794(8) 0.0321(4) Uani 1 1 d . . .
C6 C 0.7773(2) 0.76854(13) 0.90178(10) 0.0454(5) Uani 1 1 d . . .
H6A H 0.7011 0.7963 0.9108 0.054 Uiso 1 1 calc R . .
C7 C 0.8849(2) 0.81260(12) 0.91258(10) 0.0521(5) Uani 1 1 d . . .
H7A H 0.8822 0.8704 0.9287 0.063 Uiso 1 1 calc R . .
C8 C 0.9955(2) 0.77445(12) 0.90047(9) 0.0431(4) Uani 1 1 d . . .
H8A H 1.0688 0.8063 0.9080 0.052 Uiso 1 1 calc R . .
C9 C 1.00331(16) 0.68909(10) 0.87716(7) 0.0286(3) Uani 1 1 d . . .
C10 C 0.66077(17) 0.63410(13) 0.86596(9) 0.0408(4) Uani 1 1 d . . .
H10A H 0.6761 0.5921 0.8269 0.049 Uiso 1 1 calc R . .
C11 C 0.5528(2) 0.6912(2) 0.84391(18) 0.0875(11) Uani 1 1 d . . .
H11A H 0.5745 0.7231 0.8010 0.131 Uiso 1 1 calc R . .
H11B H 0.5340 0.7319 0.8820 0.131 Uiso 1 1 calc R . .
H11C H 0.4806 0.6552 0.8346 0.131 Uiso 1 1 calc R . .
C12 C 0.62685(17) 0.58294(13) 0.93230(10) 0.0443(4) Uani 1 1 d . . .
H12A H 0.6957 0.5457 0.9457 0.066 Uiso 1 1 calc R . .
H12B H 0.5543 0.5475 0.9226 0.066 Uiso 1 1 calc R . .
H12C H 0.6088 0.6228 0.9711 0.066 Uiso 1 1 calc R . .
C13 C 1.12709(15) 0.64851(11) 0.86306(8) 0.0323(4) Uani 1 1 d . . .
H13A H 1.1137 0.5862 0.8524 0.039 Uiso 1 1 calc R . .
C14 C 1.18801(18) 0.69004(15) 0.79843(10) 0.0479(5) Uani 1 1 d . . .
H14A H 1.1331 0.6853 0.7576 0.072 Uiso 1 1 calc R . .
H14B H 1.2655 0.6605 0.7881 0.072 Uiso 1 1 calc R . .
H14C H 1.2044 0.7509 0.8083 0.072 Uiso 1 1 calc R . .
C15 C 1.2122(2) 0.65491(14) 0.92763(10) 0.0505(5) Uani 1 1 d . . .
H15A H 1.2914 0.6281 0.9166 0.076 Uiso 1 1 calc R . .
H15B H 1.1744 0.6251 0.9678 0.076 Uiso 1 1 calc R . .
H15C H 1.2249 0.7156 0.9397 0.076 Uiso 1 1 calc R . .
C16 C 0.90005(14) 0.33127(9) 0.86378(7) 0.0232(3) Uani 1 1 d . . .
C17 C 1.00924(15) 0.28449(10) 0.86830(7) 0.0264(3) Uani 1 1 d . . .
C18 C 1.00132(18) 0.19746(11) 0.88621(8) 0.0346(4) Uani 1 1 d . . .
H18A H 1.0741 0.1639 0.8889 0.042 Uiso 1 1 calc R . .
C19 C 0.88966(19) 0.15977(11) 0.89999(8) 0.0385(4) Uani 1 1 d . . .
H19A H 0.8862 0.1007 0.9127 0.046 Uiso 1 1 calc R . .
C20 C 0.78241(19) 0.20707(11) 0.89553(8) 0.0362(4) Uani 1 1 d . . .
H20A H 0.7060 0.1801 0.9056 0.043 Uiso 1 1 calc R . .
C21 C 0.78454(15) 0.29357(10) 0.87651(7) 0.0266(3) Uani 1 1 d . . .
C22 C 1.13442(14) 0.32458(11) 0.85355(8) 0.0314(3) Uani 1 1 d . . .
H22A H 1.1231 0.3882 0.8489 0.038 Uiso 1 1 calc R . .
C23 C 1.22630(17) 0.30827(13) 0.91326(9) 0.0422(4) Uani 1 1 d . . .
H23A H 1.3052 0.3349 0.9014 0.063 Uiso 1 1 calc R . .
H23B H 1.2377 0.2462 0.9194 0.063 Uiso 1 1 calc R . .
H23C H 1.1949 0.3332 0.9572 0.063 Uiso 1 1 calc R . .
C24 C 1.18593(18) 0.29056(14) 0.78358(9) 0.0460(5) Uani 1 1 d . . .
H24A H 1.1266 0.3012 0.7456 0.069 Uiso 1 1 calc R . .
H24B H 1.2010 0.2286 0.7876 0.069 Uiso 1 1 calc R . .
H24C H 1.2632 0.3201 0.7727 0.069 Uiso 1 1 calc R . .
C25 C 0.66472(16) 0.34323(11) 0.87060(8) 0.0308(3) Uani 1 1 d . . .
H25A H 0.6847 0.4029 0.8546 0.037 Uiso 1 1 calc R . .
C26 C 0.60176(18) 0.34959(12) 0.94292(9) 0.0435(4) Uani 1 1 d . . .
H26A H 0.6580 0.3762 0.9769 0.065 Uiso 1 1 calc R . .
H26B H 0.5796 0.2918 0.9593 0.065 Uiso 1 1 calc R . .
H26C H 0.5274 0.3848 0.9388 0.065 Uiso 1 1 calc R . .
C27 C 0.57725(18) 0.30312(15) 0.81604(11) 0.0487(5) Uani 1 1 d . . .
H27A H 0.6184 0.3001 0.7700 0.073 Uiso 1 1 calc R . .
H27B H 0.5032 0.3387 0.8120 0.073 Uiso 1 1 calc R . .
H27C H 0.5544 0.2450 0.8313 0.073 Uiso 1 1 calc R . .
C28 C 0.78405(15) 0.52982(10) 1.07486(8) 0.0313(3) Uani 1 1 d . . .
C29 C 0.87039(15) 0.49307(11) 1.13028(7) 0.0342(3) Uani 1 1 d . . .
C30 C 0.99731(14) 0.49323(12) 1.09661(7) 0.0326(3) Uani 1 1 d . . .
C31 C 0.98161(14) 0.45955(9) 1.02066(8) 0.0277(3) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ni1 C31 1.8746(15) . ?
Ni1 C28 1.9341(14) . ?
Ni1 C1 1.9408(12) . ?
N1 C1 1.3360(17) . ?
N1 C4 1.4363(18) . ?
N1 C2 1.4811(17) . ?
N2 C1 1.3362(17) . ?
N2 C16 1.4322(18) . ?
N2 C3 1.4810(17) . ?
F1 C28 1.3857(19) . ?
F2 C28 1.3876(18) . ?
F3 C29 1.3541(17) . ?
F4 C29 1.355(2) . ?
F5 C30 1.349(2) . ?
F6 C30 1.3510(18) . ?
F7 C31 1.3629(17) . ?
F8 C31 1.3680(17) . ?
C2 C3 1.521(2) . ?
C4 C9 1.393(2) . ?
C4 C5 1.402(2) . ?
C5 C6 1.387(3) . ?
C5 C10 1.513(3) . ?
C6 C7 1.372(3) . ?
C7 C8 1.362(3) . ?
C8 C9 1.401(2) . ?
C9 C13 1.511(2) . ?
C10 C11 1.531(3) . ?
C10 C12 1.531(2) . ?
C13 C14 1.534(2) . ?
C13 C15 1.536(2) . ?
C16 C17 1.396(2) . ?
C16 C21 1.408(2) . ?
C17 C18 1.397(2) . ?
C17 C22 1.524(2) . ?
C18 C19 1.374(3) . ?
C19 C20 1.382(3) . ?
C20 C21 1.392(2) . ?
C21 C25 1.520(2) . ?
C22 C23 1.530(2) . ?
C22 C24 1.532(2) . ?
C25 C26 1.534(2) . ?
C25 C27 1.536(2) . ?
C28 C29 1.520(2) . ?
C29 C30 1.521(2) . ?
C30 C31 1.539(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
C31 Ni1 C28 86.95(6) . . ?
C31 Ni1 C1 96.64(6) . . ?
C28 Ni1 C1 174.63(6) . . ?
C1 N1 C4 124.12(11) . . ?
C1 N1 C2 113.42(11) . . ?
C4 N1 C2 122.33(11) . . ?
C1 N2 C16 127.41(11) . . ?
C1 N2 C3 112.75(11) . . ?
C16 N2 C3 119.47(11) . . ?
N1 C1 N2 108.40(11) . . ?
N1 C1 Ni1 118.59(10) . . ?
N2 C1 Ni1 132.60(10) . . ?
N1 C2 C3 102.14(12) . . ?
N2 C3 C2 102.93(12) . . ?
C9 C4 C5 122.67(14) . . ?
C9 C4 N1 118.72(13) . . ?
C5 C4 N1 118.57(13) . . ?
C6 C5 C4 117.34(17) . . ?
C6 C5 C10 122.02(17) . . ?
C4 C5 C10 120.63(14) . . ?
C7 C6 C5 121.01(18) . . ?
C6 C7 C8 120.83(17) . . ?
C7 C8 C9 121.26(19) . . ?
C4 C9 C8 116.88(16) . . ?
C4 C9 C13 122.78(14) . . ?
C8 C9 C13 120.32(16) . . ?
C5 C10 C11 113.00(18) . . ?
C5 C10 C12 110.36(15) . . ?
C11 C10 C12 109.83(17) . . ?
C9 C13 C14 110.52(14) . . ?
C9 C13 C15 111.70(15) . . ?
C14 C13 C15 110.26(14) . . ?
C17 C16 C21 122.21(13) . . ?
C17 C16 N2 118.81(13) . . ?
C21 C16 N2 118.90(13) . . ?
C16 C17 C18 117.81(16) . . ?
C16 C17 C22 122.49(14) . . ?
C18 C17 C22 119.69(15) . . ?
C19 C18 C17 120.89(17) . . ?
C18 C19 C20 120.57(15) . . ?
C19 C20 C21 121.03(17) . . ?
C20 C21 C16 117.46(16) . . ?
C20 C21 C25 119.69(15) . . ?
C16 C21 C25 122.85(13) . . ?
C17 C22 C23 112.42(14) . . ?
C17 C22 C24 110.15(14) . . ?
C23 C22 C24 109.99(14) . . ?
C21 C25 C26 110.53(13) . . ?
C21 C25 C27 112.03(14) . . ?
C26 C25 C27 110.41(15) . . ?
F1 C28 F2 103.56(13) . . ?
F1 C28 C29 106.05(13) . . ?
F2 C28 C29 107.44(12) . . ?
F1 C28 Ni1 110.56(10) . . ?
F2 C28 Ni1 116.38(11) . . ?
C29 C28 Ni1 112.05(10) . . ?
F4 C29 F3 106.32(13) . . ?
F4 C29 C30 108.15(14) . . ?
F3 C29 C30 111.25(13) . . ?
F4 C29 C28 109.70(13) . . ?
F3 C29 C28 115.48(14) . . ?
C30 C29 C28 105.79(11) . . ?
F5 C30 F6 107.37(13) . . ?
F5 C30 C29 108.31(14) . . ?
F6 C30 C29 111.98(13) . . ?
F5 C30 C31 108.91(13) . . ?
F6 C30 C31 113.32(13) . . ?
C29 C30 C31 106.84(12) . . ?
F7 C31 F8 105.13(11) . . ?
F7 C31 C30 106.98(12) . . ?
F8 C31 C30 107.48(12) . . ?
F7 C31 Ni1 111.18(10) . . ?
F8 C31 Ni1 115.03(10) . . ?
C30 C31 Ni1 110.60(10) . . ?

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
C4 N1 C1 N2 -174.72(14) . . . . ?
C2 N1 C1 N2 1.17(16) . . . . ?
C4 N1 C1 Ni1 11.72(18) . . . . ?
C2 N1 C1 Ni1 -172.39(10) . . . . ?
C16 N2 C1 N1 -177.75(14) . . . . ?
C3 N2 C1 N1 -4.85(15) . . . . ?
C16 N2 C1 Ni1 -5.4(2) . . . . ?
C3 N2 C1 Ni1 167.47(11) . . . . ?
C31 Ni1 C1 N1 -119.26(11) . . . . ?
C28 Ni1 C1 N1 12.6(7) . . . . ?
C31 Ni1 C1 N2 69.05(13) . . . . ?
C28 Ni1 C1 N2 -159.1(6) . . . . ?
C1 N1 C2 C3 2.68(19) . . . . ?
C4 N1 C2 C3 178.66(14) . . . . ?
C1 N2 C3 C2 6.31(18) . . . . ?
C16 N2 C3 C2 179.83(14) . . . . ?
N1 C2 C3 N2 -4.96(18) . . . . ?
C1 N1 C4 C9 97.89(16) . . . . ?
C2 N1 C4 C9 -77.64(18) . . . . ?
C1 N1 C4 C5 -84.25(18) . . . . ?
C2 N1 C4 C5 100.21(17) . . . . ?
C9 C4 C5 C6 -1.3(2) . . . . ?
N1 C4 C5 C6 -179.02(13) . . . . ?
C9 C4 C5 C10 -179.86(14) . . . . ?
N1 C4 C5 C10 2.4(2) . . . . ?
C4 C5 C6 C7 1.1(3) . . . . ?
C10 C5 C6 C7 179.71(17) . . . . ?
C5 C6 C7 C8 -0.3(3) . . . . ?
C6 C7 C8 C9 -0.5(3) . . . . ?
C5 C4 C9 C8 0.5(2) . . . . ?
N1 C4 C9 C8 178.30(13) . . . . ?
C5 C4 C9 C13 -178.20(14) . . . . ?
N1 C4 C9 C13 -0.4(2) . . . . ?
C7 C8 C9 C4 0.3(3) . . . . ?
C7 C8 C9 C13 179.12(17) . . . . ?
C6 C5 C10 C11 30.6(3) . . . . ?
C4 C5 C10 C11 -150.8(2) . . . . ?
C6 C5 C10 C12 -92.8(2) . . . . ?
C4 C5 C10 C12 85.75(19) . . . . ?
C4 C9 C13 C14 110.36(17) . . . . ?
C8 C9 C13 C14 -68.3(2) . . . . ?
C4 C9 C13 C15 -126.48(16) . . . . ?
C8 C9 C13 C15 54.8(2) . . . . ?
C1 N2 C16 C17 -108.00(16) . . . . ?
C3 N2 C16 C17 79.52(17) . . . . ?
C1 N2 C16 C21 75.09(18) . . . . ?
C3 N2 C16 C21 -97.39(16) . . . . ?
C21 C16 C17 C18 -0.1(2) . . . . ?
N2 C16 C17 C18 -176.87(12) . . . . ?
C21 C16 C17 C22 179.08(14) . . . . ?
N2 C16 C17 C22 2.3(2) . . . . ?
C16 C17 C18 C19 -1.0(2) . . . . ?
C22 C17 C18 C19 179.79(14) . . . . ?
C17 C18 C19 C20 0.8(2) . . . . ?
C18 C19 C20 C21 0.5(2) . . . . ?
C19 C20 C21 C16 -1.5(2) . . . . ?
C19 C20 C21 C25 178.72(14) . . . . ?
C17 C16 C21 C20 1.3(2) . . . . ?
N2 C16 C21 C20 178.13(12) . . . . ?
C17 C16 C21 C25 -178.94(13) . . . . ?
N2 C16 C21 C25 -2.1(2) . . . . ?
C16 C17 C22 C23 128.29(15) . . . . ?
C18 C17 C22 C23 -52.57(19) . . . . ?
C16 C17 C22 C24 -108.67(16) . . . . ?
C18 C17 C22 C24 70.47(18) . . . . ?
C20 C21 C25 C26 64.55(18) . . . . ?
C16 C21 C25 C26 -115.17(16) . . . . ?
C20 C21 C25 C27 -59.03(19) . . . . ?
C16 C21 C25 C27 121.25(16) . . . . ?
C31 Ni1 C28 F1 110.97(12) . . . . ?
C1 Ni1 C28 F1 -21.2(7) . . . . ?
C31 Ni1 C28 F2 -131.29(12) . . . . ?
C1 Ni1 C28 F2 96.5(6) . . . . ?
C31 Ni1 C28 C29 -7.10(12) . . . . ?
C1 Ni1 C28 C29 -139.3(6) . . . . ?
F1 C28 C29 F4 153.45(12) . . . . ?
F2 C28 C29 F4 43.20(15) . . . . ?
Ni1 C28 C29 F4 -85.83(13) . . . . ?
F1 C28 C29 F3 33.37(18) . . . . ?
F2 C28 C29 F3 -76.88(18) . . . . ?
Ni1 C28 C29 F3 154.09(12) . . . . ?
F1 C28 C29 C30 -90.13(15) . . . . ?
F2 C28 C29 C30 159.62(12) . . . . ?
Ni1 C28 C29 C30 30.59(16) . . . . ?
F4 C29 C30 F5 -169.23(12) . . . . ?
F3 C29 C30 F5 -52.83(17) . . . . ?
C28 C29 C30 F5 73.30(15) . . . . ?
F4 C29 C30 F6 -51.02(16) . . . . ?
F3 C29 C30 F6 65.38(19) . . . . ?
C28 C29 C30 F6 -168.49(13) . . . . ?
F4 C29 C30 C31 73.59(15) . . . . ?
F3 C29 C30 C31 -170.00(13) . . . . ?
C28 C29 C30 C31 -43.87(17) . . . . ?
F5 C30 C31 F7 162.14(12) . . . . ?
F6 C30 C31 F7 42.71(17) . . . . ?
C29 C30 C31 F7 -81.08(15) . . . . ?
F5 C30 C31 F8 49.67(15) . . . . ?
F6 C30 C31 F8 -69.76(17) . . . . ?
C29 C30 C31 F8 166.45(13) . . . . ?
F5 C30 C31 Ni1 -76.64(13) . . . . ?
F6 C30 C31 Ni1 163.93(11) . . . . ?
C29 C30 C31 Ni1 40.13(16) . . . . ?
C28 Ni1 C31 F7 100.11(11) . . . . ?
C1 Ni1 C31 F7 -83.90(10) . . . . ?
C28 Ni1 C31 F8 -140.57(11) . . . . ?
C1 Ni1 C31 F8 35.42(11) . . . . ?
C28 Ni1 C31 C30 -18.59(11) . . . . ?
C1 Ni1 C31 C30 157.41(11) . . . . ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        28.32
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.327
_refine_diff_density_min         -0.224
_refine_diff_density_rms         0.043
####################################################################### 
# 
# 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_tb070
_database_code_depnum_ccdc_archive 'CCDC 968467'
_audit_update_record             
;
2015-02-17 deposited with the CCDC.
2015-07-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            'Ni[κ1-(cyclo-C4F7)](SIPr)(OTf) '
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C35 H45 F10 N2 Ni O3 S'
_chemical_formula_weight         822.50

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 '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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

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

_cell_length_a                   10.2361(5)
_cell_length_b                   16.5042(8)
_cell_length_c                   22.6115(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.960(2)
_cell_angle_gamma                90.00
_cell_volume                     3819.4(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    9718
_cell_measurement_theta_min      2.18
_cell_measurement_theta_max      28.30

_exptl_crystal_description       plate
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.07
_exptl_crystal_density_meas      n/a
_exptl_crystal_density_diffrn    1.430
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1708
_exptl_absorpt_coefficient_mu    0.648
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8868
_exptl_absorpt_correction_T_max  0.9561
_exptl_absorpt_process_details   'SADABS, Bruker (2003)'

_exptl_special_details           
; 
 Data collection is performed with three batch runs at phi = 0.00 deg 
 (650 frames), at phi = 120.00 deg (650 frames), and at phi = 240.00 deg 
 (650 frames). 
 Frame width = 0.30 deg in omega. 
 Data is merged, corrected for decay (if any), and treated with multi-scan 
 absorption corrections (if required). All symmetry-equivalent reflections 
 are merged for centrosymmetric data. 
 Friedel pairs are not merged for noncentrosymmetric data. 
;

_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            65889
_diffrn_reflns_av_R_equivalents  0.0396
_diffrn_reflns_av_sigmaI/netI    0.0294
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         1.53
_diffrn_reflns_theta_max         28.36
_reflns_number_total             9440
_reflns_number_gt                7901
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX II, Bruker (2009)'
_computing_cell_refinement       'APEX II, Bruker (2009)'
_computing_data_reduction        'XPREP, Bruker (2009)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXTL, Bruker (2004)'
_computing_publication_material  'SHELXTL, Bruker (2004)'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0848P)²+3.4011P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    cconstr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         9440
_refine_ls_number_parameters     469
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0727
_refine_ls_R_factor_gt           0.0580
_refine_ls_wR_factor_ref         0.1513
_refine_ls_wR_factor_gt          0.1410
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.046
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Ni1 Ni 0.20815(3) 0.144159(17) 0.284401(13) 0.01957(10) Uani 1 1 d . . .
S1 S -0.01861(6) 0.10953(5) 0.31725(3) 0.03584(17) Uani 1 1 d . . .
F1 F 0.41170(15) 0.24332(10) 0.24488(8) 0.0375(4) Uani 1 1 d . . .
F2 F 0.12619(18) 0.31848(10) 0.29917(8) 0.0426(4) Uani 1 1 d . . .
F3 F 0.2916(2) 0.37751(11) 0.25963(10) 0.0575(6) Uani 1 1 d . . .
F4 F 0.0134(2) 0.29812(17) 0.19097(10) 0.0715(7) Uani 1 1 d . . .
F5 F 0.1641(3) 0.37864(14) 0.15907(10) 0.0851(9) Uani 1 1 d . . .
F6 F 0.1616(2) 0.17512(13) 0.15508(9) 0.0596(6) Uani 1 1 d . . .
F7 F 0.3205(2) 0.25664(14) 0.13752(8) 0.0651(7) Uani 1 1 d . . .
F8 F 0.0549(2) 0.21165(14) 0.39948(9) 0.0618(6) Uani 1 1 d . . .
F9 F -0.0807(3) 0.1217(2) 0.42744(12) 0.0905(9) Uani 1 1 d . . .
F10 F -0.1468(3) 0.2199(2) 0.37300(13) 0.0921(9) Uani 1 1 d . . .
O1 O 0.01824(18) 0.16962(13) 0.27275(9) 0.0360(4) Uani 1 1 d . . .
O2 O 0.10174(18) 0.06413(11) 0.33105(9) 0.0322(4) Uani 1 1 d . . .
O3 O -0.1349(2) 0.06442(18) 0.30723(12) 0.0608(7) Uani 1 1 d . . .
N1 N 0.42117(19) 0.09091(12) 0.35499(8) 0.0214(4) Uani 1 1 d . . .
N2 N 0.45325(18) 0.06598(11) 0.26136(8) 0.0195(4) Uani 1 1 d . . .
C1 C 0.3713(2) 0.09959(12) 0.30017(10) 0.0154(4) Uani 1 1 d . . .
C2 C 0.5554(3) 0.0562(2) 0.35363(12) 0.0356(6) Uani 1 1 d . . .
H2A H 0.5685 0.0147 0.3848 0.043 Uiso 1 1 calc R . .
H2B H 0.6228 0.0989 0.3583 0.043 Uiso 1 1 calc R . .
C3 C 0.5575(2) 0.01910(16) 0.29277(11) 0.0278(5) Uani 1 1 d . . .
H3A H 0.6434 0.0267 0.2741 0.033 Uiso 1 1 calc R . .
H3B H 0.5365 -0.0394 0.2940 0.033 Uiso 1 1 calc R . .
C4 C 0.3581(2) 0.10977(14) 0.40964(10) 0.0212(4) Uani 1 1 d . . .
C5 C 0.3689(3) 0.18857(15) 0.43342(11) 0.0273(5) Uani 1 1 d . . .
C6 C 0.3080(3) 0.20371(18) 0.48653(13) 0.0392(7) Uani 1 1 d . . .
H6A H 0.3138 0.2563 0.5035 0.047 Uiso 1 1 calc R . .
C7 C 0.2390(3) 0.1441(2) 0.51532(13) 0.0446(8) Uani 1 1 d . . .
H7A H 0.1956 0.1564 0.5510 0.054 Uiso 1 1 calc R . .
C8 C 0.2330(3) 0.06648(19) 0.49221(12) 0.0397(7) Uani 1 1 d . . .
H8A H 0.1873 0.0255 0.5130 0.048 Uiso 1 1 calc R . .
C9 C 0.2927(3) 0.04729(15) 0.43915(11) 0.0271(5) Uani 1 1 d . . .
C10 C 0.4481(3) 0.25536(16) 0.40451(12) 0.0345(6) Uani 1 1 d . . .
H10A H 0.4674 0.2386 0.3631 0.041 Uiso 1 1 calc R . .
C11 C 0.3745(4) 0.3361(2) 0.40251(18) 0.0553(9) Uani 1 1 d . . .
H11A H 0.2909 0.3288 0.3815 0.083 Uiso 1 1 calc R . .
H11B H 0.4270 0.3765 0.3819 0.083 Uiso 1 1 calc R . .
H11C H 0.3586 0.3546 0.4429 0.083 Uiso 1 1 calc R . .
C12 C 0.5776(3) 0.2673(2) 0.43811(16) 0.0491(8) Uani 1 1 d . . .
H12A H 0.6247 0.2157 0.4402 0.074 Uiso 1 1 calc R . .
H12B H 0.5604 0.2866 0.4782 0.074 Uiso 1 1 calc R . .
H12C H 0.6308 0.3073 0.4174 0.074 Uiso 1 1 calc R . .
C13 C 0.2929(3) -0.04015(16) 0.41783(13) 0.0356(6) Uani 1 1 d . . .
H13A H 0.3218 -0.0410 0.3758 0.043 Uiso 1 1 calc R . .
C14 C 0.1593(4) -0.0812(2) 0.42088(16) 0.0517(9) Uani 1 1 d . . .
H14A H 0.0957 -0.0505 0.3970 0.078 Uiso 1 1 calc R . .
H14B H 0.1310 -0.0827 0.4621 0.078 Uiso 1 1 calc R . .
H14C H 0.1656 -0.1365 0.4056 0.078 Uiso 1 1 calc R . .
C15 C 0.3909(5) -0.0896(2) 0.4554(2) 0.0665(12) Uani 1 1 d . . .
H15A H 0.4773 -0.0641 0.4538 0.100 Uiso 1 1 calc R . .
H15B H 0.3960 -0.1448 0.4398 0.100 Uiso 1 1 calc R . .
H15C H 0.3620 -0.0912 0.4965 0.100 Uiso 1 1 calc R . .
C16 C 0.4306(2) 0.05483(14) 0.19886(10) 0.0219(5) Uani 1 1 d . . .
C17 C 0.5175(3) 0.09119(16) 0.15956(12) 0.0283(5) Uani 1 1 d . . .
C18 C 0.4947(3) 0.07928(19) 0.09872(12) 0.0387(7) Uani 1 1 d . . .
H18A H 0.5517 0.1035 0.0711 0.046 Uiso 1 1 calc R . .
C19 C 0.3918(3) 0.0334(2) 0.07849(12) 0.0426(7) Uani 1 1 d . . .
H19A H 0.3765 0.0275 0.0372 0.051 Uiso 1 1 calc R . .
C20 C 0.3106(3) -0.00428(18) 0.11787(12) 0.0362(6) Uani 1 1 d . . .
H20A H 0.2409 -0.0371 0.1032 0.043 Uiso 1 1 calc R . .
C21 C 0.3282(2) 0.00468(14) 0.17893(11) 0.0259(5) Uani 1 1 d . . .
C22 C 0.6389(3) 0.13779(18) 0.17899(13) 0.0373(6) Uani 1 1 d . . .
H22A H 0.6344 0.1471 0.2226 0.045 Uiso 1 1 calc R . .
C23 C 0.6491(4) 0.2207(2) 0.14842(17) 0.0540(9) Uani 1 1 d . . .
H23A H 0.7290 0.2481 0.1619 0.081 Uiso 1 1 calc R . .
H23B H 0.5730 0.2538 0.1583 0.081 Uiso 1 1 calc R . .
H23C H 0.6516 0.2130 0.1055 0.081 Uiso 1 1 calc R . .
C24 C 0.7620(3) 0.0876(3) 0.16672(17) 0.0540(9) Uani 1 1 d . . .
H24A H 0.7548 0.0345 0.1859 0.081 Uiso 1 1 calc R . .
H24B H 0.8391 0.1160 0.1825 0.081 Uiso 1 1 calc R . .
H24C H 0.7707 0.0802 0.1240 0.081 Uiso 1 1 calc R . .
C25 C 0.2418(3) -0.04338(16) 0.22009(13) 0.0332(6) Uani 1 1 d . . .
H25A H 0.2548 -0.0214 0.2610 0.040 Uiso 1 1 calc R . .
C26 C 0.0972(3) -0.0356(2) 0.20376(17) 0.0531(9) Uani 1 1 d . . .
H26A H 0.0723 0.0217 0.2037 0.080 Uiso 1 1 calc R . .
H26B H 0.0451 -0.0650 0.2327 0.080 Uiso 1 1 calc R . .
H26C H 0.0814 -0.0585 0.1643 0.080 Uiso 1 1 calc R . .
C27 C 0.2842(5) -0.13280(19) 0.22067(19) 0.0610(11) Uani 1 1 d . . .
H27A H 0.3772 -0.1364 0.2313 0.091 Uiso 1 1 calc R . .
H27B H 0.2694 -0.1563 0.1813 0.091 Uiso 1 1 calc R . .
H27C H 0.2329 -0.1626 0.2497 0.091 Uiso 1 1 calc R . .
C28 C 0.2778(3) 0.23217(14) 0.24171(11) 0.0266(5) Uani 1 1 d . . .
C29 C 0.2092(3) 0.31499(16) 0.25389(13) 0.0351(6) Uani 1 1 d . . .
C30 C 0.1426(4) 0.3132(2) 0.19149(14) 0.0500(9) Uani 1 1 d . . .
C31 C 0.2285(3) 0.23859(17) 0.17630(12) 0.0379(7) Uani 1 1 d . . .
C32 C -0.0490(3) 0.1700(3) 0.38339(17) 0.0535(9) Uani 1 1 d . . .
C33 C 0.0545(6) -0.1877(4) -0.0269(3) 0.0943(16) Uani 1 1 d . . .
H33A H 0.0220 -0.2381 -0.0096 0.141 Uiso 1 1 calc R . .
H33B H 0.1495 -0.1846 -0.0212 0.141 Uiso 1 1 calc R . .
H33C H 0.0331 -0.1867 -0.0693 0.141 Uiso 1 1 calc R . .
C34 C -0.0090(10) -0.1160(4) 0.0030(3) 0.128(3) Uani 1 1 d . . .
H34A H -0.1047 -0.1207 -0.0033 0.154 Uiso 1 1 calc R . .
H34B H 0.0082 -0.1208 0.0460 0.154 Uiso 1 1 calc R . .
C35 C 0.0293(6) -0.0363(3) -0.0149(2) 0.0885(15) Uani 1 1 d . . .
H35A H 0.0100 -0.0314 -0.0578 0.106 Uiso 1 1 calc R . .
H35B H 0.1254 -0.0325 -0.0098 0.106 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ni1 C1 1.854(2) . ?
Ni1 C28 1.890(2) . ?
Ni1 O1 2.0020(18) . ?
Ni1 O2 2.0204(18) . ?
Ni1 S1 2.5148(7) . ?
S1 O3 1.419(2) . ?
S1 O1 1.467(2) . ?
S1 O2 1.471(2) . ?
S1 C32 1.829(4) . ?
F1 C28 1.384(3) . ?
F2 C29 1.343(3) . ?
F3 C29 1.338(4) . ?
F4 C30 1.346(5) . ?
F5 C30 1.325(4) . ?
F6 C31 1.336(4) . ?
F7 C31 1.331(4) . ?
F8 C32 1.313(5) . ?
F9 C32 1.320(4) . ?
F10 C32 1.315(4) . ?
N1 C1 1.340(3) . ?
N1 C4 1.438(3) . ?
N1 C2 1.489(3) . ?
N2 C1 1.344(3) . ?
N2 C16 1.440(3) . ?
N2 C3 1.489(3) . ?
C2 C3 1.507(4) . ?
C4 C9 1.404(3) . ?
C4 C5 1.411(3) . ?
C5 C6 1.385(4) . ?
C5 C10 1.522(4) . ?
C6 C7 1.380(4) . ?
C7 C8 1.385(4) . ?
C8 C9 1.392(4) . ?
C9 C13 1.522(4) . ?
C10 C11 1.530(4) . ?
C10 C12 1.530(4) . ?
C13 C14 1.528(4) . ?
C13 C15 1.538(4) . ?
C16 C21 1.404(3) . ?
C16 C17 1.403(4) . ?
C17 C18 1.405(4) . ?
C17 C22 1.520(4) . ?
C18 C19 1.370(5) . ?
C19 C20 1.377(4) . ?
C20 C21 1.397(4) . ?
C21 C25 1.518(4) . ?
C22 C23 1.537(4) . ?
C22 C24 1.538(5) . ?
C25 C26 1.524(5) . ?
C25 C27 1.538(4) . ?
C28 C31 1.558(4) . ?
C28 C29 1.563(3) . ?
C29 C30 1.557(5) . ?
C30 C31 1.555(4) . ?
C33 C34 1.514(9) . ?
C34 C35 1.434(9) . ?
C35 C35 1.505(11) 3 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 Ni1 C28 93.27(10) . . ?
C1 Ni1 O1 168.00(9) . . ?
C28 Ni1 O1 98.34(10) . . ?
C1 Ni1 O2 97.58(8) . . ?
C28 Ni1 O2 168.58(9) . . ?
O1 Ni1 O2 71.04(8) . . ?
C1 Ni1 S1 133.31(7) . . ?
C28 Ni1 S1 133.10(8) . . ?
O1 Ni1 S1 35.66(6) . . ?
O2 Ni1 S1 35.79(6) . . ?
O3 S1 O1 118.03(14) . . ?
O3 S1 O2 117.65(15) . . ?
O1 S1 O2 105.42(11) . . ?
O3 S1 C32 105.23(17) . . ?
O1 S1 C32 103.98(16) . . ?
O2 S1 C32 104.94(14) . . ?
O3 S1 Ni1 148.01(13) . . ?
O1 S1 Ni1 52.73(7) . . ?
O2 S1 Ni1 53.45(7) . . ?
C32 S1 Ni1 106.75(12) . . ?
S1 O1 Ni1 91.61(9) . . ?
S1 O2 Ni1 90.76(9) . . ?
C1 N1 C4 127.02(19) . . ?
C1 N1 C2 111.06(19) . . ?
C4 N1 C2 121.91(19) . . ?
C1 N2 C16 126.97(19) . . ?
C1 N2 C3 110.70(18) . . ?
C16 N2 C3 120.27(18) . . ?
N1 C1 N2 109.11(18) . . ?
N1 C1 Ni1 123.25(16) . . ?
N2 C1 Ni1 127.47(16) . . ?
N1 C2 C3 101.69(19) . . ?
N2 C3 C2 101.73(19) . . ?
C9 C4 C5 122.1(2) . . ?
C9 C4 N1 118.3(2) . . ?
C5 C4 N1 119.6(2) . . ?
C6 C5 C4 117.6(2) . . ?
C6 C5 C10 119.5(2) . . ?
C4 C5 C10 122.9(2) . . ?
C7 C6 C5 121.4(3) . . ?
C6 C7 C8 120.1(3) . . ?
C7 C8 C9 121.2(3) . . ?
C8 C9 C4 117.5(2) . . ?
C8 C9 C13 119.5(2) . . ?
C4 C9 C13 122.9(2) . . ?
C11 C10 C5 112.2(3) . . ?
C11 C10 C12 108.9(3) . . ?
C5 C10 C12 110.1(2) . . ?
C9 C13 C14 113.6(3) . . ?
C9 C13 C15 109.4(2) . . ?
C14 C13 C15 108.5(3) . . ?
C21 C16 C17 121.8(2) . . ?
C21 C16 N2 119.8(2) . . ?
C17 C16 N2 118.3(2) . . ?
C16 C17 C18 117.6(2) . . ?
C16 C17 C22 123.9(2) . . ?
C18 C17 C22 118.4(2) . . ?
C19 C18 C17 121.2(3) . . ?
C18 C19 C20 120.2(3) . . ?
C19 C20 C21 121.5(3) . . ?
C20 C21 C16 117.6(2) . . ?
C20 C21 C25 118.9(2) . . ?
C16 C21 C25 123.4(2) . . ?
C17 C22 C23 112.4(3) . . ?
C17 C22 C24 110.1(3) . . ?
C23 C22 C24 109.7(3) . . ?
C21 C25 C26 112.4(3) . . ?
C21 C25 C27 109.8(3) . . ?
C26 C25 C27 110.8(3) . . ?
F1 C28 C31 110.2(2) . . ?
F1 C28 C29 108.8(2) . . ?
C31 C28 C29 88.21(19) . . ?
F1 C28 Ni1 117.22(16) . . ?
C31 C28 Ni1 114.71(19) . . ?
C29 C28 Ni1 114.07(17) . . ?
F3 C29 F2 107.4(2) . . ?
F3 C29 C30 111.6(2) . . ?
F2 C29 C30 114.7(3) . . ?
F3 C29 C28 114.1(2) . . ?
F2 C29 C28 117.6(2) . . ?
C30 C29 C28 90.9(2) . . ?
F5 C30 F4 108.5(3) . . ?
F5 C30 C31 115.1(3) . . ?
F4 C30 C31 114.2(3) . . ?
F5 C30 C29 114.3(3) . . ?
F4 C30 C29 115.3(3) . . ?
C31 C30 C29 88.5(2) . . ?
F7 C31 F6 107.6(3) . . ?
F7 C31 C30 112.1(2) . . ?
F6 C31 C30 114.3(3) . . ?
F7 C31 C28 114.8(3) . . ?
F6 C31 C28 116.3(2) . . ?
C30 C31 C28 91.1(2) . . ?
F10 C32 F9 108.5(3) . . ?
F10 C32 F8 109.4(4) . . ?
F9 C32 F8 108.4(3) . . ?
F10 C32 S1 109.6(3) . . ?
F9 C32 S1 109.6(3) . . ?
F8 C32 S1 111.4(2) . . ?
C35 C34 C33 118.0(6) . . ?
C34 C35 C35 119.3(7) . 3 ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 Ni1 S1 O3 -88.7(2) . . . . ?
C28 Ni1 S1 O3 99.6(3) . . . . ?
O1 Ni1 S1 O3 84.0(3) . . . . ?
O2 Ni1 S1 O3 -84.5(2) . . . . ?
C1 Ni1 S1 O1 -172.77(14) . . . . ?
C28 Ni1 S1 O1 15.56(16) . . . . ?
O2 Ni1 S1 O1 -168.52(15) . . . . ?
C1 Ni1 S1 O2 -4.25(14) . . . . ?
C28 Ni1 S1 O2 -175.92(15) . . . . ?
O1 Ni1 S1 O2 168.52(15) . . . . ?
C1 Ni1 S1 C32 92.18(16) . . . . ?
C28 Ni1 S1 C32 -79.49(17) . . . . ?
O1 Ni1 S1 C32 -95.05(17) . . . . ?
O2 Ni1 S1 C32 96.43(16) . . . . ?
O3 S1 O1 Ni1 -143.36(15) . . . . ?
O2 S1 O1 Ni1 -9.55(13) . . . . ?
C32 S1 O1 Ni1 100.59(14) . . . . ?
C1 Ni1 O1 S1 26.1(5) . . . . ?
C28 Ni1 O1 S1 -168.58(12) . . . . ?
O2 Ni1 O1 S1 7.07(10) . . . . ?
O3 S1 O2 Ni1 143.47(14) . . . . ?
O1 S1 O2 Ni1 9.46(13) . . . . ?
C32 S1 O2 Ni1 -99.99(14) . . . . ?
C1 Ni1 O2 S1 176.88(10) . . . . ?
C28 Ni1 O2 S1 15.2(5) . . . . ?
O1 Ni1 O2 S1 -7.05(9) . . . . ?
C4 N1 C1 N2 -172.3(2) . . . . ?
C2 N1 C1 N2 6.5(3) . . . . ?
C4 N1 C1 Ni1 3.3(3) . . . . ?
C2 N1 C1 Ni1 -177.91(18) . . . . ?
C16 N2 C1 N1 173.2(2) . . . . ?
C3 N2 C1 N1 9.7(2) . . . . ?
C16 N2 C1 Ni1 -2.1(3) . . . . ?
C3 N2 C1 Ni1 -165.61(16) . . . . ?
C28 Ni1 C1 N1 117.23(19) . . . . ?
O1 Ni1 C1 N1 -77.4(5) . . . . ?
O2 Ni1 C1 N1 -59.19(19) . . . . ?
S1 Ni1 C1 N1 -56.7(2) . . . . ?
C28 Ni1 C1 N2 -68.1(2) . . . . ?
O1 Ni1 C1 N2 97.3(5) . . . . ?
O2 Ni1 C1 N2 115.50(19) . . . . ?
S1 Ni1 C1 N2 118.00(17) . . . . ?
C1 N1 C2 C3 -19.2(3) . . . . ?
C4 N1 C2 C3 159.7(2) . . . . ?
C1 N2 C3 C2 -21.1(3) . . . . ?
C16 N2 C3 C2 174.1(2) . . . . ?
N1 C2 C3 N2 22.6(3) . . . . ?
C1 N1 C4 C9 94.5(3) . . . . ?
C2 N1 C4 C9 -84.2(3) . . . . ?
C1 N1 C4 C5 -88.6(3) . . . . ?
C2 N1 C4 C5 92.7(3) . . . . ?
C9 C4 C5 C6 -2.4(4) . . . . ?
N1 C4 C5 C6 -179.2(2) . . . . ?
C9 C4 C5 C10 175.2(2) . . . . ?
N1 C4 C5 C10 -1.6(4) . . . . ?
C4 C5 C6 C7 -0.1(4) . . . . ?
C10 C5 C6 C7 -177.7(3) . . . . ?
C5 C6 C7 C8 2.1(5) . . . . ?
C6 C7 C8 C9 -1.7(5) . . . . ?
C7 C8 C9 C4 -0.6(4) . . . . ?
C7 C8 C9 C13 175.2(3) . . . . ?
C5 C4 C9 C8 2.7(4) . . . . ?
N1 C4 C9 C8 179.5(2) . . . . ?
C5 C4 C9 C13 -172.9(2) . . . . ?
N1 C4 C9 C13 3.9(4) . . . . ?
C6 C5 C10 C11 -47.4(4) . . . . ?
C4 C5 C10 C11 135.1(3) . . . . ?
C6 C5 C10 C12 74.1(3) . . . . ?
C4 C5 C10 C12 -103.4(3) . . . . ?
C8 C9 C13 C14 47.4(4) . . . . ?
C4 C9 C13 C14 -137.1(3) . . . . ?
C8 C9 C13 C15 -74.0(4) . . . . ?
C4 C9 C13 C15 101.6(3) . . . . ?
C1 N2 C16 C21 -62.8(3) . . . . ?
C3 N2 C16 C21 99.3(3) . . . . ?
C1 N2 C16 C17 120.9(3) . . . . ?
C3 N2 C16 C17 -77.0(3) . . . . ?
C21 C16 C17 C18 3.3(4) . . . . ?
N2 C16 C17 C18 179.6(2) . . . . ?
C21 C16 C17 C22 -172.6(2) . . . . ?
N2 C16 C17 C22 3.6(4) . . . . ?
C16 C17 C18 C19 -0.5(4) . . . . ?
C22 C17 C18 C19 175.7(3) . . . . ?
C17 C18 C19 C20 -2.0(5) . . . . ?
C18 C19 C20 C21 1.6(5) . . . . ?
C19 C20 C21 C16 1.2(4) . . . . ?
C19 C20 C21 C25 -175.4(3) . . . . ?
C17 C16 C21 C20 -3.7(4) . . . . ?
N2 C16 C21 C20 -179.8(2) . . . . ?
C17 C16 C21 C25 172.8(2) . . . . ?
N2 C16 C21 C25 -3.4(4) . . . . ?
C16 C17 C22 C23 -130.8(3) . . . . ?
C18 C17 C22 C23 53.3(4) . . . . ?
C16 C17 C22 C24 106.6(3) . . . . ?
C18 C17 C22 C24 -69.3(3) . . . . ?
C20 C21 C25 C26 -49.7(3) . . . . ?
C16 C21 C25 C26 133.9(3) . . . . ?
C20 C21 C25 C27 74.1(3) . . . . ?
C16 C21 C25 C27 -102.3(3) . . . . ?
C1 Ni1 C28 F1 -11.0(2) . . . . ?
O1 Ni1 C28 F1 172.08(18) . . . . ?
O2 Ni1 C28 F1 150.9(4) . . . . ?
S1 Ni1 C28 F1 162.99(13) . . . . ?
C1 Ni1 C28 C31 120.63(19) . . . . ?
O1 Ni1 C28 C31 -56.34(19) . . . . ?
O2 Ni1 C28 C31 -77.6(5) . . . . ?
S1 Ni1 C28 C31 -65.4(2) . . . . ?
C1 Ni1 C28 C29 -139.7(2) . . . . ?
O1 Ni1 C28 C29 43.3(2) . . . . ?
O2 Ni1 C28 C29 22.1(6) . . . . ?
S1 Ni1 C28 C29 34.2(2) . . . . ?
F1 C28 C29 F3 5.1(3) . . . . ?
C31 C28 C29 F3 -105.6(3) . . . . ?
Ni1 C28 C29 F3 138.0(2) . . . . ?
F1 C28 C29 F2 -122.0(3) . . . . ?
C31 C28 C29 F2 127.3(3) . . . . ?
Ni1 C28 C29 F2 10.9(3) . . . . ?
F1 C28 C29 C30 119.3(2) . . . . ?
C31 C28 C29 C30 8.6(2) . . . . ?
Ni1 C28 C29 C30 -107.8(2) . . . . ?
F3 C29 C30 F5 -9.2(4) . . . . ?
F2 C29 C30 F5 113.3(3) . . . . ?
C28 C29 C30 F5 -125.6(3) . . . . ?
F3 C29 C30 F4 -136.0(3) . . . . ?
F2 C29 C30 F4 -13.5(4) . . . . ?
C28 C29 C30 F4 107.6(3) . . . . ?
F3 C29 C30 C31 107.8(3) . . . . ?
F2 C29 C30 C31 -129.7(2) . . . . ?
C28 C29 C30 C31 -8.6(2) . . . . ?
F5 C30 C31 F7 7.5(5) . . . . ?
F4 C30 C31 F7 134.0(3) . . . . ?
C29 C30 C31 F7 -108.8(3) . . . . ?
F5 C30 C31 F6 -115.4(3) . . . . ?
F4 C30 C31 F6 11.2(4) . . . . ?
C29 C30 C31 F6 128.3(3) . . . . ?
F5 C30 C31 C28 124.9(3) . . . . ?
F4 C30 C31 C28 -108.6(3) . . . . ?
C29 C30 C31 C28 8.6(2) . . . . ?
F1 C28 C31 F7 -2.8(3) . . . . ?
C29 C28 C31 F7 106.5(3) . . . . ?
Ni1 C28 C31 F7 -137.7(2) . . . . ?
F1 C28 C31 F6 124.1(3) . . . . ?
C29 C28 C31 F6 -126.6(3) . . . . ?
Ni1 C28 C31 F6 -10.8(3) . . . . ?
F1 C28 C31 C30 -117.9(2) . . . . ?
C29 C28 C31 C30 -8.6(2) . . . . ?
Ni1 C28 C31 C30 107.2(2) . . . . ?
O3 S1 C32 F10 -62.3(3) . . . . ?
O1 S1 C32 F10 62.4(3) . . . . ?
O2 S1 C32 F10 172.9(3) . . . . ?
Ni1 S1 C32 F10 117.2(3) . . . . ?
O3 S1 C32 F9 56.6(3) . . . . ?
O1 S1 C32 F9 -178.7(2) . . . . ?
O2 S1 C32 F9 -68.2(3) . . . . ?
Ni1 S1 C32 F9 -123.9(2) . . . . ?
O3 S1 C32 F8 176.5(3) . . . . ?
O1 S1 C32 F8 -58.8(3) . . . . ?
O2 S1 C32 F8 51.7(3) . . . . ?
Ni1 S1 C32 F8 -4.0(3) . . . . ?
C33 C34 C35 C35 -178.4(7) . . . 3 ?

_diffrn_measured_fraction_theta_max 0.988
_diffrn_reflns_theta_full        28.36
_diffrn_measured_fraction_theta_full 0.988
_refine_diff_density_max         0.944
_refine_diff_density_min         -0.717
_refine_diff_density_rms         0.078
####################################################################### 
# 
# 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_tb132_5
_database_code_depnum_ccdc_archive 'CCDC 1028645'
_audit_update_record             
;
2015-02-17 deposited with the CCDC.
2015-07-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            '[Ni[k3-(CF2)3CF(O2CCH3)-}(SIPr)] '
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C33 H41 F7 N2 Ni O2'
_chemical_formula_weight         689.39

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   9.7181(4)
_cell_length_b                   18.2160(7)
_cell_length_c                   19.2228(7)
_cell_angle_alpha                90
_cell_angle_beta                 92.180(2)
_cell_angle_gamma                90
_cell_volume                     3400.5(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    5916
_cell_measurement_theta_min      2.57
_cell_measurement_theta_max      23.25

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      n/a
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.347
_exptl_crystal_F_000             1440
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.140
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.090
_exptl_absorpt_coefficient_mu    0.640
_shelx_estimated_absorpt_T_min   0.916
_shelx_estimated_absorpt_T_max   0.945
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.535198
_exptl_absorpt_correction_T_max  0.744894
_exptl_absorpt_process_details   'SADABS, Bruker (2003)'

_exptl_special_details           
; 
 Data collection is performed with three batch runs at phi = 0.00 deg 
 (650 frames), at phi = 120.00 deg (650 frames), and at phi = 240.00 deg 
 (650 frames). 
 Frame width = 0.30 deg in omega. 
 Data is merged, corrected for decay (if any), and treated with multi-scan 
 absorption corrections (if required). All symmetry-equivalent reflections 
 are merged for centrosymmetric data. 
 Friedel pairs are not merged for noncentrosymmetric data. 
;

_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11781
_diffrn_reflns_av_unetI/netI     0.0735
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         1.541
_diffrn_reflns_theta_max         23.430
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measured_fraction_theta_full 0.791
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_Laue_measured_fraction_full 0.791
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_point_group_measured_fraction_full 0.791
_reflns_number_total             6216
_reflns_number_gt                4696
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'APEX II, Bruker (2009)'
_computing_cell_refinement       'APEX II, Bruker (2009)'
_computing_data_reduction        'XPREP, Bruker (2009)'
_computing_structure_solution    'SHELXS-03 (Sheldrick, 2003)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'SHELXTL, Bruker (2004)'
_computing_publication_material  'SHELXTL, Bruker (2004)'

_refine_special_details          
; 
 Refined as a 2-component twin. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0364P)²+11.4852P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6216
_refine_ls_number_parameters     407
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1053
_refine_ls_R_factor_gt           0.0687
_refine_ls_wR_factor_ref         0.1475
_refine_ls_wR_factor_gt          0.1292
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_restrained_S_all      1.062
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Ni1 Ni 0.64607(8) 0.80806(4) 0.78121(4) 0.0286(2) Uani 1 1 d . . . . .
F1 F 0.5860(4) 0.6593(2) 0.7936(3) 0.0607(13) Uani 1 1 d . . . . .
F2 F 0.6183(4) 0.8300(2) 0.92527(19) 0.0468(10) Uani 1 1 d . . . . .
F3 F 0.6599(4) 0.6920(2) 0.9293(2) 0.0588(11) Uani 1 1 d . . . . .
F4 F 0.9242(4) 0.7177(2) 0.8123(2) 0.0555(11) Uani 1 1 d . . . . .
F5 F 0.8244(5) 0.61694(19) 0.8457(2) 0.0558(12) Uani 1 1 d . . . . .
F6 F 0.8669(5) 0.7321(2) 0.9465(2) 0.0585(12) Uani 1 1 d . . . . .
F7 F 0.8197(4) 0.85194(18) 0.8841(2) 0.0448(10) Uani 1 1 d . . . . .
O1 O 0.6412(5) 0.7940(2) 0.6796(2) 0.0415(12) Uani 1 1 d . . . . .
O2 O 0.7365(5) 0.6870(3) 0.7109(2) 0.0478(12) Uani 1 1 d . . . . .
N1 N 0.6099(5) 0.9712(2) 0.8023(3) 0.0241(11) Uani 1 1 d . . . . .
N2 N 0.4344(5) 0.9129(2) 0.7561(2) 0.0250(11) Uani 1 1 d . . . . .
C1 C 0.5656(6) 0.9048(3) 0.7808(3) 0.0243(13) Uani 1 1 d . . . . .
C2 C 0.5119(6) 1.0301(3) 0.7827(4) 0.0344(16) Uani 1 1 d . . . . .
H2A H 0.5412 1.0569 0.7410 0.041 Uiso 1 1 calc R U . . .
H2B H 0.5012 1.0653 0.8214 0.041 Uiso 1 1 calc R U . . .
C3 C 0.3797(6) 0.9873(3) 0.7674(4) 0.0321(15) Uani 1 1 d . . . . .
H3A H 0.3184 0.9887 0.8074 0.039 Uiso 1 1 calc R U . . .
H3B H 0.3294 1.0062 0.7254 0.039 Uiso 1 1 calc R U . . .
C4 C 0.7498(6) 0.9935(3) 0.8180(3) 0.0270(14) Uani 1 1 d . . . . .
C5 C 0.8445(7) 0.9929(3) 0.7648(3) 0.0309(15) Uani 1 1 d . . . . .
C6 C 0.9748(7) 1.0234(3) 0.7805(4) 0.0409(17) Uani 1 1 d . . . . .
H6A H 1.0415 1.0248 0.7456 0.049 Uiso 1 1 calc R U . . .
C7 C 1.0069(7) 1.0512(3) 0.8452(4) 0.0402(18) Uani 1 1 d . . . . .
H7A H 1.0956 1.0716 0.8546 0.048 Uiso 1 1 calc R U . . .
C8 C 0.9133(7) 1.0501(3) 0.8966(4) 0.0392(17) Uani 1 1 d . . . . .
H8A H 0.9387 1.0688 0.9414 0.047 Uiso 1 1 calc R U . . .
C9 C 0.7817(6) 1.0221(3) 0.8843(3) 0.0278(14) Uani 1 1 d . . . . .
C10 C 0.8146(7) 0.9632(4) 0.6926(4) 0.0433(18) Uani 1 1 d . . . . .
H10A H 0.7194 0.9423 0.6917 0.052 Uiso 1 1 calc R U . . .
C11 C 0.9134(9) 0.9007(5) 0.6757(5) 0.078(3) Uani 1 1 d . . . . .
H11A H 0.9101 0.8629 0.7119 0.118 Uiso 1 1 calc R U . . .
H11B H 1.0074 0.9200 0.6739 0.118 Uiso 1 1 calc R U . . .
H11C H 0.8861 0.8792 0.6306 0.118 Uiso 1 1 calc R U . . .
C12 C 0.8166(11) 1.0238(6) 0.6378(4) 0.090(3) Uani 1 1 d . . . . .
H12A H 0.7523 1.0627 0.6500 0.135 Uiso 1 1 calc R U . . .
H12B H 0.7890 1.0034 0.5922 0.135 Uiso 1 1 calc R U . . .
H12C H 0.9098 1.0441 0.6360 0.135 Uiso 1 1 calc R U . . .
C13 C 0.6791(7) 1.0225(3) 0.9417(3) 0.0350(15) Uani 1 1 d . . . . .
H13A H 0.5962 0.9941 0.9250 0.042 Uiso 1 1 calc R U . . .
C14 C 0.7369(8) 0.9859(4) 1.0076(4) 0.0466(18) Uani 1 1 d . . . . .
H14A H 0.7659 0.9357 0.9969 0.070 Uiso 1 1 calc R U . . .
H14B H 0.6658 0.9844 1.0424 0.070 Uiso 1 1 calc R U . . .
H14C H 0.8163 1.0139 1.0260 0.070 Uiso 1 1 calc R U . . .
C15 C 0.6330(8) 1.1013(4) 0.9573(4) 0.0495(19) Uani 1 1 d . . . . .
H15A H 0.5975 1.1245 0.9142 0.074 Uiso 1 1 calc R U . . .
H15B H 0.7117 1.1295 0.9763 0.074 Uiso 1 1 calc R U . . .
H15C H 0.5605 1.1002 0.9913 0.074 Uiso 1 1 calc R U . . .
C16 C 0.3518(6) 0.8552(3) 0.7249(3) 0.0301(14) Uani 1 1 d . . . . .
C17 C 0.3344(6) 0.8542(3) 0.6526(3) 0.0348(16) Uani 1 1 d . . . . .
C18 C 0.2591(8) 0.7959(4) 0.6231(4) 0.050(2) Uani 1 1 d . . . . .
H18A H 0.2450 0.7931 0.5740 0.060 Uiso 1 1 calc R U . . .
C19 C 0.2053(8) 0.7427(4) 0.6647(4) 0.057(2) Uani 1 1 d . . . . .
H19A H 0.1575 0.7024 0.6438 0.068 Uiso 1 1 calc R U . . .
C20 C 0.2192(7) 0.7467(4) 0.7357(4) 0.0486(19) Uani 1 1 d . . . . .
H20A H 0.1784 0.7098 0.7631 0.058 Uiso 1 1 calc R U . . .
C21 C 0.2916(6) 0.8033(3) 0.7684(3) 0.0323(14) Uani 1 1 d . . . . .
C22 C 0.3889(7) 0.9135(4) 0.6051(3) 0.0404(17) Uani 1 1 d . . . . .
H22A H 0.4487 0.9468 0.6346 0.049 Uiso 1 1 calc R U . . .
C23 C 0.4761(9) 0.8843(5) 0.5472(4) 0.065(2) Uani 1 1 d . . . . .
H23A H 0.5524 0.8552 0.5673 0.097 Uiso 1 1 calc R U . . .
H23B H 0.5130 0.9256 0.5210 0.097 Uiso 1 1 calc R U . . .
H23C H 0.4191 0.8535 0.5158 0.097 Uiso 1 1 calc R U . . .
C24 C 0.2698(9) 0.9599(5) 0.5744(4) 0.065(2) Uani 1 1 d . . . . .
H24A H 0.2143 0.9784 0.6121 0.097 Uiso 1 1 calc R U . . .
H24B H 0.2122 0.9295 0.5429 0.097 Uiso 1 1 calc R U . . .
H24C H 0.3069 1.0013 0.5484 0.097 Uiso 1 1 calc R U . . .
C25 C 0.2918(6) 0.8116(4) 0.8466(3) 0.0401(16) Uani 1 1 d . . . . .
H25A H 0.3700 0.8447 0.8608 0.048 Uiso 1 1 calc R U . . .
C26 C 0.3104(9) 0.7401(4) 0.8859(4) 0.062(2) Uani 1 1 d . . . . .
H26A H 0.3962 0.7166 0.8728 0.092 Uiso 1 1 calc R U . . .
H26B H 0.2326 0.7075 0.8745 0.092 Uiso 1 1 calc R U . . .
H26C H 0.3143 0.7500 0.9361 0.092 Uiso 1 1 calc R U . . .
C27 C 0.1584(7) 0.8491(4) 0.8664(4) 0.0471(18) Uani 1 1 d . . . . .
H27A H 0.1484 0.8957 0.8412 0.071 Uiso 1 1 calc R U . . .
H27B H 0.1610 0.8585 0.9166 0.071 Uiso 1 1 calc R U . . .
H27C H 0.0801 0.8171 0.8540 0.071 Uiso 1 1 calc R U . . .
C28 C 0.6959(8) 0.7359(4) 0.6638(4) 0.0428(18) Uani 1 1 d . . . . .
C29 C 0.7247(10) 0.7158(5) 0.5915(4) 0.073(3) Uani 1 1 d . . . . .
H29A H 0.6892 0.7542 0.5598 0.110 Uiso 1 1 calc R U . . .
H29B H 0.6796 0.6691 0.5798 0.110 Uiso 1 1 calc R U . . .
H29C H 0.8243 0.7109 0.5868 0.110 Uiso 1 1 calc R U . . .
C30 C 0.6960(8) 0.7075(4) 0.7794(4) 0.0467(19) Uani 1 1 d . . . . .
C31 C 0.8027(8) 0.6888(4) 0.8344(3) 0.0426(17) Uani 1 1 d . . . . .
C32 C 0.7068(6) 0.8058(4) 0.8761(3) 0.0343(15) Uani 1 1 d . . . . .
C39 C 0.7613(7) 0.7295(4) 0.8983(3) 0.0383(17) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ni1 C30 1.895(7) . ?
Ni1 C32 1.896(6) . ?
Ni1 C1 1.928(6) . ?
Ni1 O1 1.969(4) . ?
F1 C30 1.418(8) . ?
F2 C32 1.375(7) . ?
F3 C39 1.355(8) . ?
F4 C31 1.375(8) . ?
F5 C31 1.343(7) . ?
F6 C39 1.358(8) . ?
F7 C32 1.386(7) . ?
O1 C28 1.227(8) . ?
O2 C28 1.320(8) . ?
O2 C30 1.437(8) . ?
N1 C1 1.343(7) . ?
N1 C4 1.440(7) . ?
N1 C2 1.474(7) . ?
N2 C1 1.351(7) . ?
N2 C16 1.439(7) . ?
N2 C3 1.475(7) . ?
C2 C3 1.521(8) . ?
C4 C9 1.401(8) . ?
C4 C5 1.402(9) . ?
C5 C6 1.405(9) . ?
C5 C10 1.507(9) . ?
C6 C7 1.368(10) . ?
C7 C8 1.369(10) . ?
C8 C9 1.388(9) . ?
C9 C13 1.514(9) . ?
C10 C12 1.526(10) . ?
C10 C11 1.533(11) . ?
C13 C14 1.521(9) . ?
C13 C15 1.537(9) . ?
C16 C17 1.393(9) . ?
C16 C21 1.405(9) . ?
C17 C18 1.398(9) . ?
C17 C22 1.523(9) . ?
C18 C19 1.373(10) . ?
C19 C20 1.367(10) . ?
C20 C21 1.387(9) . ?
C21 C25 1.510(9) . ?
C22 C23 1.521(10) . ?
C22 C24 1.533(10) . ?
C25 C26 1.514(9) . ?
C25 C27 1.527(9) . ?
C28 C29 1.475(9) . ?
C30 C31 1.492(10) . ?
C31 C39 1.502(9) . ?
C32 C39 1.542(9) . ?

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
C30 Ni1 C32 85.8(3) . . ?
C30 Ni1 C1 170.9(3) . . ?
C32 Ni1 C1 97.8(3) . . ?
C30 Ni1 O1 81.5(2) . . ?
C32 Ni1 O1 161.1(2) . . ?
C1 Ni1 O1 96.9(2) . . ?
C28 O1 Ni1 111.3(4) . . ?
C28 O2 C30 111.6(5) . . ?
C1 N1 C4 127.4(5) . . ?
C1 N1 C2 112.3(4) . . ?
C4 N1 C2 116.3(4) . . ?
C1 N2 C16 124.8(5) . . ?
C1 N2 C3 112.9(4) . . ?
C16 N2 C3 122.3(5) . . ?
N1 C1 N2 107.3(5) . . ?
N1 C1 Ni1 134.1(4) . . ?
N2 C1 Ni1 118.6(4) . . ?
N1 C2 C3 102.1(4) . . ?
N2 C3 C2 101.1(4) . . ?
C9 C4 C5 122.6(6) . . ?
C9 C4 N1 118.0(5) . . ?
C5 C4 N1 119.0(5) . . ?
C4 C5 C6 116.8(6) . . ?
C4 C5 C10 124.5(6) . . ?
C6 C5 C10 118.7(6) . . ?
C7 C6 C5 120.9(7) . . ?
C6 C7 C8 121.1(6) . . ?
C7 C8 C9 121.1(6) . . ?
C8 C9 C4 117.5(6) . . ?
C8 C9 C13 120.2(6) . . ?
C4 C9 C13 122.3(5) . . ?
C5 C10 C12 111.6(6) . . ?
C5 C10 C11 111.2(6) . . ?
C12 C10 C11 111.5(7) . . ?
C9 C13 C14 111.8(5) . . ?
C9 C13 C15 110.5(5) . . ?
C14 C13 C15 110.4(6) . . ?
C17 C16 C21 123.1(5) . . ?
C17 C16 N2 118.1(5) . . ?
C21 C16 N2 118.8(6) . . ?
C16 C17 C18 117.2(6) . . ?
C16 C17 C22 123.8(6) . . ?
C18 C17 C22 118.9(6) . . ?
C19 C18 C17 120.3(7) . . ?
C20 C19 C18 121.3(6) . . ?
C19 C20 C21 121.4(7) . . ?
C20 C21 C16 116.6(6) . . ?
C20 C21 C25 120.5(6) . . ?
C16 C21 C25 122.7(5) . . ?
C23 C22 C17 114.0(6) . . ?
C23 C22 C24 110.1(6) . . ?
C17 C22 C24 110.3(6) . . ?
C21 C25 C26 114.1(6) . . ?
C21 C25 C27 108.9(5) . . ?
C26 C25 C27 110.2(6) . . ?
O1 C28 O2 122.2(6) . . ?
O1 C28 C29 123.2(7) . . ?
O2 C28 C29 114.6(6) . . ?
F1 C30 O2 104.5(5) . . ?
F1 C30 C31 103.4(5) . . ?
O2 C30 C31 112.5(6) . . ?
F1 C30 Ni1 113.5(5) . . ?
O2 C30 Ni1 110.3(5) . . ?
C31 C30 Ni1 112.3(5) . . ?
F5 C31 F4 107.0(6) . . ?
F5 C31 C30 116.0(6) . . ?
F4 C31 C30 106.0(5) . . ?
F5 C31 C39 113.2(6) . . ?
F4 C31 C39 108.9(6) . . ?
C30 C31 C39 105.4(6) . . ?
F2 C32 F7 104.0(5) . . ?
F2 C32 C39 108.4(5) . . ?
F7 C32 C39 104.7(5) . . ?
F2 C32 Ni1 118.3(4) . . ?
F7 C32 Ni1 108.1(4) . . ?
C39 C32 Ni1 112.1(4) . . ?
F3 C39 F6 105.1(5) . . ?
F3 C39 C31 109.5(5) . . ?
F6 C39 C31 110.9(6) . . ?
F3 C39 C32 109.1(5) . . ?
F6 C39 C32 113.6(5) . . ?
C31 C39 C32 108.5(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
C4 N1 C1 N2 -165.1(5) . . . . ?
C2 N1 C1 N2 -8.5(7) . . . . ?
C4 N1 C1 Ni1 17.0(10) . . . . ?
C2 N1 C1 Ni1 173.6(5) . . . . ?
C16 N2 C1 N1 176.8(5) . . . . ?
C3 N2 C1 N1 -6.0(7) . . . . ?
C16 N2 C1 Ni1 -4.9(8) . . . . ?
C3 N2 C1 Ni1 172.3(4) . . . . ?
C1 N1 C2 C3 18.5(7) . . . . ?
C4 N1 C2 C3 177.9(5) . . . . ?
C1 N2 C3 C2 16.8(7) . . . . ?
C16 N2 C3 C2 -165.9(6) . . . . ?
N1 C2 C3 N2 -19.5(6) . . . . ?
C1 N1 C4 C9 -123.5(6) . . . . ?
C2 N1 C4 C9 80.7(7) . . . . ?
C1 N1 C4 C5 63.0(8) . . . . ?
C2 N1 C4 C5 -92.8(7) . . . . ?
C9 C4 C5 C6 -0.6(8) . . . . ?
N1 C4 C5 C6 172.5(5) . . . . ?
C9 C4 C5 C10 -179.6(6) . . . . ?
N1 C4 C5 C10 -6.4(8) . . . . ?
C4 C5 C6 C7 0.9(9) . . . . ?
C10 C5 C6 C7 179.9(6) . . . . ?
C5 C6 C7 C8 0.1(10) . . . . ?
C6 C7 C8 C9 -1.3(10) . . . . ?
C7 C8 C9 C4 1.6(9) . . . . ?
C7 C8 C9 C13 -179.1(6) . . . . ?
C5 C4 C9 C8 -0.6(8) . . . . ?
N1 C4 C9 C8 -173.8(5) . . . . ?
C5 C4 C9 C13 -179.9(5) . . . . ?
N1 C4 C9 C13 6.9(8) . . . . ?
C4 C5 C10 C12 114.3(8) . . . . ?
C6 C5 C10 C12 -64.6(9) . . . . ?
C4 C5 C10 C11 -120.4(7) . . . . ?
C6 C5 C10 C11 60.6(8) . . . . ?
C8 C9 C13 C14 -53.6(7) . . . . ?
C4 C9 C13 C14 125.7(6) . . . . ?
C8 C9 C13 C15 69.8(7) . . . . ?
C4 C9 C13 C15 -110.9(6) . . . . ?
C1 N2 C16 C17 -102.5(7) . . . . ?
C3 N2 C16 C17 80.5(7) . . . . ?
C1 N2 C16 C21 78.2(8) . . . . ?
C3 N2 C16 C21 -98.8(7) . . . . ?
C21 C16 C17 C18 -3.5(9) . . . . ?
N2 C16 C17 C18 177.2(6) . . . . ?
C21 C16 C17 C22 174.7(6) . . . . ?
N2 C16 C17 C22 -4.6(9) . . . . ?
C16 C17 C18 C19 0.2(10) . . . . ?
C22 C17 C18 C19 -178.2(7) . . . . ?
C17 C18 C19 C20 2.5(12) . . . . ?
C18 C19 C20 C21 -1.9(12) . . . . ?
C19 C20 C21 C16 -1.3(10) . . . . ?
C19 C20 C21 C25 172.9(7) . . . . ?
C17 C16 C21 C20 4.1(9) . . . . ?
N2 C16 C21 C20 -176.6(5) . . . . ?
C17 C16 C21 C25 -169.9(6) . . . . ?
N2 C16 C21 C25 9.4(9) . . . . ?
C16 C17 C22 C23 127.2(7) . . . . ?
C18 C17 C22 C23 -54.6(9) . . . . ?
C16 C17 C22 C24 -108.4(7) . . . . ?
C18 C17 C22 C24 69.9(8) . . . . ?
C20 C21 C25 C26 43.4(9) . . . . ?
C16 C21 C25 C26 -142.8(6) . . . . ?
C20 C21 C25 C27 -80.2(8) . . . . ?
C16 C21 C25 C27 93.6(7) . . . . ?
Ni1 O1 C28 O2 7.4(9) . . . . ?
Ni1 O1 C28 C29 -171.1(7) . . . . ?
C30 O2 C28 O1 5.8(10) . . . . ?
C30 O2 C28 C29 -175.6(7) . . . . ?
C28 O2 C30 F1 106.1(6) . . . . ?
C28 O2 C30 C31 -142.5(6) . . . . ?
C28 O2 C30 Ni1 -16.3(7) . . . . ?
C32 Ni1 C30 F1 92.5(5) . . . . ?
O1 Ni1 C30 F1 -101.4(5) . . . . ?
C32 Ni1 C30 O2 -150.6(5) . . . . ?
O1 Ni1 C30 O2 15.5(5) . . . . ?
C32 Ni1 C30 C31 -24.2(5) . . . . ?
O1 Ni1 C30 C31 141.8(6) . . . . ?
F1 C30 C31 F5 44.7(8) . . . . ?
O2 C30 C31 F5 -67.4(8) . . . . ?
Ni1 C30 C31 F5 167.4(5) . . . . ?
F1 C30 C31 F4 163.3(5) . . . . ?
O2 C30 C31 F4 51.2(7) . . . . ?
Ni1 C30 C31 F4 -74.0(6) . . . . ?
F1 C30 C31 C39 -81.4(6) . . . . ?
O2 C30 C31 C39 166.5(5) . . . . ?
Ni1 C30 C31 C39 41.4(7) . . . . ?
C30 Ni1 C32 F2 -126.7(5) . . . . ?
C1 Ni1 C32 F2 44.8(5) . . . . ?
O1 Ni1 C32 F2 -174.3(5) . . . . ?
C30 Ni1 C32 F7 115.6(4) . . . . ?
C1 Ni1 C32 F7 -72.9(4) . . . . ?
O1 Ni1 C32 F7 68.0(9) . . . . ?
C30 Ni1 C32 C39 0.6(5) . . . . ?
C1 Ni1 C32 C39 172.2(4) . . . . ?
O1 Ni1 C32 C39 -46.9(10) . . . . ?
F5 C31 C39 F3 -47.9(8) . . . . ?
F4 C31 C39 F3 -166.7(5) . . . . ?
C30 C31 C39 F3 79.9(6) . . . . ?
F5 C31 C39 F6 67.6(7) . . . . ?
F4 C31 C39 F6 -51.2(7) . . . . ?
C30 C31 C39 F6 -164.6(5) . . . . ?
F5 C31 C39 C32 -167.0(6) . . . . ?
F4 C31 C39 C32 74.3(7) . . . . ?
C30 C31 C39 C32 -39.1(7) . . . . ?
F2 C32 C39 F3 35.6(7) . . . . ?
F7 C32 C39 F3 146.1(5) . . . . ?
Ni1 C32 C39 F3 -96.9(5) . . . . ?
F2 C32 C39 F6 -81.3(7) . . . . ?
F7 C32 C39 F6 29.3(7) . . . . ?
Ni1 C32 C39 F6 146.2(5) . . . . ?
F2 C32 C39 C31 154.8(5) . . . . ?
F7 C32 C39 C31 -94.6(6) . . . . ?
Ni1 C32 C39 C31 22.3(7) . . . . ?

_refine_diff_density_max         0.871
_refine_diff_density_min         -0.423
_refine_diff_density_rms         0.070

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_tb069
_database_code_depnum_ccdc_archive 'CCDC 1412522'
_audit_update_record             
;
2015-07-13 deposited with the CCDC.
2015-07-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C37 H46 F8 N2 Ni O'
_chemical_formula_weight         745.47

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

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

_cell_length_a                   16.5255(8)
_cell_length_b                   10.6186(5)
_cell_length_c                   20.8839(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 101.931(2)
_cell_angle_gamma                90.00
_cell_volume                     3585.5(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    9963
_cell_measurement_theta_min      2.52
_cell_measurement_theta_max      28.34

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      n/a
_exptl_crystal_density_diffrn    1.381
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1560
_exptl_absorpt_coefficient_mu    0.614
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8767
_exptl_absorpt_correction_T_max  0.8974
_exptl_absorpt_process_details   'SADABS, Bruker (2003)'

_exptl_special_details           
; 
 Data collection is performed with three batch runs at phi = 0.00 deg 
 (650 frames), at phi = 120.00 deg (650 frames), and at phi = 240.00 deg 
 (650 frames). 
 Frame width = 0.30 deg in omega. 
 Data is merged, corrected for decay (if any), and treated with multi-scan 
 absorption corrections (if required). All symmetry-equivalent reflections 
 are merged for centrosymmetric data. 
 Friedel pairs are not merged for noncentrosymmetric data. 
;

_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            50510
_diffrn_reflns_av_R_equivalents  0.0234
_diffrn_reflns_av_sigmaI/netI    0.0174
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         1.99
_diffrn_reflns_theta_max         28.36
_reflns_number_total             8894
_reflns_number_gt                7623
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX II, Bruker (2009)'
_computing_cell_refinement       'APEX II, Bruker (2009)'
_computing_data_reduction        'XPREP, Bruker (2009)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXTL, Bruker (2004)'
_computing_publication_material  'SHELXTL, Bruker (2004)'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0468P)²+0.9032P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         8894
_refine_ls_number_parameters     442
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0376
_refine_ls_R_factor_gt           0.0299
_refine_ls_wR_factor_ref         0.0831
_refine_ls_wR_factor_gt          0.0782
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_restrained_S_all      1.027
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Ni1 Ni 0.259437(9) 0.391266(14) 0.026876(7) 0.02028(5) Uani 1 1 d . . .
F1 F 0.37096(5) 0.39858(9) 0.14196(4) 0.0438(2) Uani 1 1 d . . .
F2 F 0.25253(7) 0.32089(8) 0.15422(4) 0.0435(2) Uani 1 1 d . . .
F3 F 0.30582(6) 0.57026(9) 0.20271(4) 0.0460(2) Uani 1 1 d . . .
F4 F 0.18288(5) 0.54272(8) 0.14363(4) 0.0396(2) Uani 1 1 d . . .
F5 F 0.36165(6) 0.65357(10) 0.09917(5) 0.0522(3) Uani 1 1 d . . .
F6 F 0.24446(7) 0.74683(8) 0.09923(5) 0.0527(3) Uani 1 1 d . . .
F7 F 0.28374(6) 0.63290(8) -0.02127(5) 0.0456(2) Uani 1 1 d . . .
F8 F 0.16470(5) 0.60659(8) 0.00577(5) 0.0406(2) Uani 1 1 d . . .
O1 O 0.22923(6) 0.39250(9) -0.07030(5) 0.0337(2) Uani 1 1 d . . .
H1A H 0.2256 0.4735 -0.0906 0.050 Uiso 1 1 d R . .
H1B H 0.1797 0.3400 -0.0899 0.050 Uiso 1 1 d R . .
N1 N 0.20466(6) 0.12998(10) 0.00367(5) 0.0233(2) Uani 1 1 d . . .
N2 N 0.33013(6) 0.13332(9) 0.06046(5) 0.02006(19) Uani 1 1 d . . .
C1 C 0.26748(6) 0.20733(11) 0.03052(5) 0.0187(2) Uani 1 1 d . . .
C2 C 0.22048(8) -0.00268(12) 0.02310(7) 0.0301(3) Uani 1 1 d . . .
H2A H 0.2031 -0.0604 -0.0145 0.036 Uiso 1 1 calc R . .
H2B H 0.1921 -0.0266 0.0587 0.036 Uiso 1 1 calc R . .
C3 C 0.31369(8) -0.00184(12) 0.04644(7) 0.0271(3) Uani 1 1 d . . .
H3A H 0.3311 -0.0538 0.0863 0.032 Uiso 1 1 calc R . .
H3B H 0.3420 -0.0322 0.0120 0.032 Uiso 1 1 calc R . .
C4 C 0.13102(7) 0.16376(12) -0.04273(6) 0.0235(2) Uani 1 1 d . . .
C5 C 0.12905(8) 0.13926(13) -0.10929(6) 0.0293(3) Uani 1 1 d . . .
C6 C 0.05631(9) 0.16817(16) -0.15389(7) 0.0381(3) Uani 1 1 d . . .
H6A H 0.0529 0.1517 -0.1991 0.046 Uiso 1 1 calc R . .
C7 C -0.01079(9) 0.22010(16) -0.13385(7) 0.0408(3) Uani 1 1 d . . .
H7A H -0.0593 0.2405 -0.1653 0.049 Uiso 1 1 calc R . .
C8 C -0.00777(8) 0.24249(15) -0.06836(7) 0.0357(3) Uani 1 1 d . . .
H8A H -0.0543 0.2786 -0.0551 0.043 Uiso 1 1 calc R . .
C9 C 0.06279(7) 0.21277(12) -0.02117(6) 0.0268(3) Uani 1 1 d . . .
C10 C 0.20126(9) 0.08074(15) -0.13364(7) 0.0369(3) Uani 1 1 d . . .
H10A H 0.2489 0.0742 -0.0955 0.044 Uiso 1 1 calc R . .
C11 C 0.17988(13) -0.05194(18) -0.15970(11) 0.0622(5) Uani 1 1 d . . .
H11A H 0.1367 -0.0475 -0.1996 0.093 Uiso 1 1 calc R . .
H11B H 0.1599 -0.1017 -0.1266 0.093 Uiso 1 1 calc R . .
H11C H 0.2293 -0.0919 -0.1696 0.093 Uiso 1 1 calc R . .
C12 C 0.22918(12) 0.15949(19) -0.18626(9) 0.0507(4) Uani 1 1 d . . .
H12A H 0.2740 0.1158 -0.2014 0.076 Uiso 1 1 calc R . .
H12B H 0.2490 0.2416 -0.1680 0.076 Uiso 1 1 calc R . .
H12C H 0.1825 0.1717 -0.2232 0.076 Uiso 1 1 calc R . .
C13 C 0.06192(8) 0.22983(14) 0.05059(7) 0.0316(3) Uani 1 1 d . . .
H13A H 0.1176 0.2062 0.0767 0.038 Uiso 1 1 calc R . .
C14 C -0.00238(12) 0.14218(19) 0.07020(9) 0.0516(4) Uani 1 1 d . . .
H14A H -0.0578 0.1670 0.0470 0.077 Uiso 1 1 calc R . .
H14B H 0.0009 0.1481 0.1175 0.077 Uiso 1 1 calc R . .
H14C H 0.0086 0.0553 0.0587 0.077 Uiso 1 1 calc R . .
C15 C 0.04454(10) 0.36575(16) 0.06656(9) 0.0470(4) Uani 1 1 d . . .
H15A H 0.0881 0.4203 0.0565 0.071 Uiso 1 1 calc R . .
H15B H 0.0434 0.3728 0.1131 0.071 Uiso 1 1 calc R . .
H15C H -0.0091 0.3917 0.0403 0.071 Uiso 1 1 calc R . .
C16 C 0.41517(7) 0.16949(11) 0.08281(6) 0.0214(2) Uani 1 1 d . . .
C17 C 0.45290(8) 0.14341(13) 0.14806(6) 0.0267(3) Uani 1 1 d . . .
C18 C 0.53665(9) 0.17080(16) 0.16804(7) 0.0388(3) Uani 1 1 d . . .
H18A H 0.5638 0.1539 0.2119 0.047 Uiso 1 1 calc R . .
C19 C 0.58079(9) 0.22214(18) 0.12518(8) 0.0466(4) Uani 1 1 d . . .
H19A H 0.6378 0.2413 0.1399 0.056 Uiso 1 1 calc R . .
C20 C 0.54299(8) 0.24596(16) 0.06112(8) 0.0391(3) Uani 1 1 d . . .
H20A H 0.5742 0.2815 0.0322 0.047 Uiso 1 1 calc R . .
C21 C 0.45937(7) 0.21857(12) 0.03815(6) 0.0259(2) Uani 1 1 d . . .
C22 C 0.40635(9) 0.08872(14) 0.19705(6) 0.0319(3) Uani 1 1 d . . .
H22A H 0.3465 0.0836 0.1755 0.038 Uiso 1 1 calc R . .
C23 C 0.43648(12) -0.04483(16) 0.21747(8) 0.0473(4) Uani 1 1 d . . .
H23A H 0.4276 -0.0994 0.1788 0.071 Uiso 1 1 calc R . .
H23B H 0.4055 -0.0778 0.2491 0.071 Uiso 1 1 calc R . .
H23C H 0.4956 -0.0425 0.2375 0.071 Uiso 1 1 calc R . .
C24 C 0.41399(12) 0.17230(17) 0.25786(7) 0.0468(4) Uani 1 1 d . . .
H24A H 0.3979 0.2587 0.2444 0.070 Uiso 1 1 calc R . .
H24B H 0.4713 0.1715 0.2824 0.070 Uiso 1 1 calc R . .
H24C H 0.3776 0.1401 0.2857 0.070 Uiso 1 1 calc R . .
C25 C 0.42252(8) 0.24028(13) -0.03378(6) 0.0273(3) Uani 1 1 d . . .
H25A H 0.3622 0.2200 -0.0413 0.033 Uiso 1 1 calc R . .
C26 C 0.43088(10) 0.37772(14) -0.05315(8) 0.0393(3) Uani 1 1 d . . .
H26A H 0.4890 0.3963 -0.0529 0.059 Uiso 1 1 calc R . .
H26B H 0.4114 0.4328 -0.0218 0.059 Uiso 1 1 calc R . .
H26C H 0.3976 0.3922 -0.0971 0.059 Uiso 1 1 calc R . .
C27 C 0.46178(10) 0.15197(16) -0.07672(7) 0.0411(3) Uani 1 1 d . . .
H27A H 0.4360 0.1657 -0.1228 0.062 Uiso 1 1 calc R . .
H27B H 0.4533 0.0644 -0.0649 0.062 Uiso 1 1 calc R . .
H27C H 0.5212 0.1693 -0.0699 0.062 Uiso 1 1 calc R . .
C28 C 0.28696(8) 0.40844(12) 0.11874(6) 0.0272(3) Uani 1 1 d . . .
C29 C 0.26433(8) 0.53894(13) 0.14179(7) 0.0300(3) Uani 1 1 d . . .
C30 C 0.27963(9) 0.63351(12) 0.09073(8) 0.0335(3) Uani 1 1 d . . .
C31 C 0.24743(8) 0.57169(13) 0.02470(7) 0.0284(3) Uani 1 1 d . . .
C32 C 0.08908(18) 0.4302(2) -0.24836(11) 0.0750(7) Uani 1 1 d . . .
H32A H 0.0530 0.3610 -0.2616 0.090 Uiso 1 1 calc R . .
C33 C 0.07547(16) 0.5068(2) -0.19959(11) 0.0705(6) Uani 1 1 d . . .
H33A H 0.0296 0.4915 -0.1797 0.085 Uiso 1 1 calc R . .
C34 C 0.12545(18) 0.6024(2) -0.17959(13) 0.0812(8) Uani 1 1 d . . .
H34A H 0.1164 0.6544 -0.1448 0.097 Uiso 1 1 calc R . .
C35 C 0.19123(18) 0.6264(3) -0.2096(2) 0.1066(12) Uani 1 1 d . . .
H35A H 0.2272 0.6953 -0.1955 0.128 Uiso 1 1 calc R . .
C36 C 0.20457(17) 0.5495(3) -0.26043(18) 0.0959(9) Uani 1 1 d . . .
H36A H 0.2488 0.5660 -0.2819 0.115 Uiso 1 1 calc R . .
C37 C 0.15303(19) 0.4502(2) -0.27861(12) 0.0807(7) Uani 1 1 d . . .
H37A H 0.1618 0.3951 -0.3124 0.097 Uiso 1 1 calc R . .


_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 C28 1.8868(13) . ?
Ni1 C31 1.9257(14) . ?
Ni1 C1 1.9580(12) . ?
Ni1 O1 1.9872(10) . ?
F1 C28 1.3766(15) . ?
F2 C28 1.3825(16) . ?
F3 C29 1.3560(15) . ?
F4 C29 1.3550(15) . ?
F5 C30 1.3472(16) . ?
F6 C30 1.3638(16) . ?
F7 C31 1.3937(15) . ?
F8 C31 1.3926(15) . ?
N1 C1 1.3513(15) . ?
N1 C4 1.4356(15) . ?
N1 C2 1.4742(16) . ?
N2 C1 1.3464(15) . ?
N2 C16 1.4384(14) . ?
N2 C3 1.4787(15) . ?
C2 C3 1.5166(17) . ?
C4 C9 1.3981(17) . ?
C4 C5 1.4080(18) . ?
C5 C6 1.3941(19) . ?
C5 C10 1.5232(19) . ?
C6 C7 1.379(2) . ?
C7 C8 1.379(2) . ?
C8 C9 1.3984(18) . ?
C9 C13 1.5126(18) . ?
C10 C12 1.526(2) . ?
C10 C11 1.525(2) . ?
C13 C15 1.522(2) . ?
C13 C14 1.531(2) . ?
C16 C21 1.3989(17) . ?
C16 C17 1.4039(16) . ?
C17 C18 1.3912(19) . ?
C17 C22 1.5170(18) . ?
C18 C19 1.378(2) . ?
C19 C20 1.378(2) . ?
C20 C21 1.3965(18) . ?
C21 C25 1.5173(17) . ?
C22 C23 1.534(2) . ?
C22 C24 1.533(2) . ?
C25 C26 1.528(2) . ?
C25 C27 1.5313(19) . ?
C28 C29 1.5383(18) . ?
C29 C30 1.523(2) . ?
C30 C31 1.521(2) . ?
C32 C33 1.358(3) . ?
C32 C37 1.355(4) . ?
C33 C34 1.321(4) . ?
C34 C35 1.386(5) . ?
C35 C36 1.392(4) . ?
C36 C37 1.359(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C28 Ni1 C31 85.98(6) . . ?
C28 Ni1 C1 93.26(5) . . ?
C31 Ni1 C1 177.64(5) . . ?
C28 Ni1 O1 174.05(5) . . ?
C31 Ni1 O1 88.07(5) . . ?
C1 Ni1 O1 92.69(4) . . ?
C1 N1 C4 126.83(10) . . ?
C1 N1 C2 112.92(10) . . ?
C4 N1 C2 120.12(10) . . ?
C1 N2 C16 126.93(10) . . ?
C1 N2 C3 112.48(9) . . ?
C16 N2 C3 116.78(9) . . ?
N2 C1 N1 106.79(10) . . ?
N2 C1 Ni1 129.78(8) . . ?
N1 C1 Ni1 123.37(8) . . ?
N1 C2 C3 101.14(9) . . ?
N2 C3 C2 101.67(9) . . ?
C9 C4 C5 122.07(11) . . ?
C9 C4 N1 120.21(11) . . ?
C5 C4 N1 117.62(11) . . ?
C6 C5 C4 117.37(12) . . ?
C6 C5 C10 119.57(12) . . ?
C4 C5 C10 123.04(12) . . ?
C7 C6 C5 121.44(13) . . ?
C8 C7 C6 120.24(13) . . ?
C7 C8 C9 120.93(13) . . ?
C4 C9 C8 117.88(12) . . ?
C4 C9 C13 122.49(11) . . ?
C8 C9 C13 119.59(11) . . ?
C5 C10 C12 113.03(13) . . ?
C5 C10 C11 110.87(13) . . ?
C12 C10 C11 109.36(14) . . ?
C9 C13 C15 111.81(13) . . ?
C9 C13 C14 109.97(12) . . ?
C15 C13 C14 110.19(13) . . ?
C21 C16 C17 122.16(11) . . ?
C21 C16 N2 119.52(10) . . ?
C17 C16 N2 118.07(11) . . ?
C18 C17 C16 117.68(12) . . ?
C18 C17 C22 119.32(12) . . ?
C16 C17 C22 123.00(11) . . ?
C19 C18 C17 121.01(13) . . ?
C18 C19 C20 120.56(13) . . ?
C19 C20 C21 120.87(14) . . ?
C20 C21 C16 117.68(12) . . ?
C20 C21 C25 118.33(12) . . ?
C16 C21 C25 123.97(11) . . ?
C17 C22 C23 111.15(12) . . ?
C17 C22 C24 111.76(13) . . ?
C23 C22 C24 109.78(12) . . ?
C21 C25 C26 111.55(11) . . ?
C21 C25 C27 110.78(11) . . ?
C26 C25 C27 110.94(11) . . ?
F1 C28 F2 104.88(10) . . ?
F1 C28 C29 104.54(10) . . ?
F2 C28 C29 106.53(10) . . ?
F1 C28 Ni1 111.37(9) . . ?
F2 C28 Ni1 116.14(9) . . ?
C29 C28 Ni1 112.47(9) . . ?
F4 C29 F3 106.18(11) . . ?
F4 C29 C30 108.05(11) . . ?
F3 C29 C30 111.73(11) . . ?
F4 C29 C28 110.04(11) . . ?
F3 C29 C28 113.96(11) . . ?
C30 C29 C28 106.77(11) . . ?
F5 C30 F6 106.72(11) . . ?
F5 C30 C31 109.93(12) . . ?
F6 C30 C31 114.85(12) . . ?
F5 C30 C29 108.71(12) . . ?
F6 C30 C29 110.71(12) . . ?
C31 C30 C29 105.82(10) . . ?
F8 C31 F7 102.57(10) . . ?
F8 C31 C30 106.35(11) . . ?
F7 C31 C30 107.68(11) . . ?
F8 C31 Ni1 111.21(9) . . ?
F7 C31 Ni1 115.04(9) . . ?
C30 C31 Ni1 113.14(9) . . ?
C33 C32 C37 121.4(3) . . ?
C34 C33 C32 120.5(3) . . ?
C33 C34 C35 119.7(2) . . ?
C34 C35 C36 120.0(3) . . ?
C37 C36 C35 118.6(3) . . ?
C36 C37 C32 119.7(2) . . ?

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
C16 N2 C1 N1 164.81(11) . . . . ?
C3 N2 C1 N1 7.73(13) . . . . ?
C16 N2 C1 Ni1 -18.07(17) . . . . ?
C3 N2 C1 Ni1 -175.15(8) . . . . ?
C4 N1 C1 N2 -167.90(11) . . . . ?
C2 N1 C1 N2 7.84(13) . . . . ?
C4 N1 C1 Ni1 14.75(16) . . . . ?
C2 N1 C1 Ni1 -169.51(8) . . . . ?
C28 Ni1 C1 N2 -53.84(11) . . . . ?
C31 Ni1 C1 N2 -124.8(13) . . . . ?
O1 Ni1 C1 N2 126.33(10) . . . . ?
C28 Ni1 C1 N1 122.86(10) . . . . ?
C31 Ni1 C1 N1 51.9(13) . . . . ?
O1 Ni1 C1 N1 -56.97(10) . . . . ?
C1 N1 C2 C3 -19.03(14) . . . . ?
C4 N1 C2 C3 157.03(11) . . . . ?
C1 N2 C3 C2 -19.01(13) . . . . ?
C16 N2 C3 C2 -178.60(10) . . . . ?
N1 C2 C3 N2 20.98(13) . . . . ?
C1 N1 C4 C9 -85.03(16) . . . . ?
C2 N1 C4 C9 99.50(14) . . . . ?
C1 N1 C4 C5 98.36(15) . . . . ?
C2 N1 C4 C5 -77.11(15) . . . . ?
C9 C4 C5 C6 1.3(2) . . . . ?
N1 C4 C5 C6 177.80(12) . . . . ?
C9 C4 C5 C10 -177.33(13) . . . . ?
N1 C4 C5 C10 -0.78(19) . . . . ?
C4 C5 C6 C7 0.7(2) . . . . ?
C10 C5 C6 C7 179.37(15) . . . . ?
C5 C6 C7 C8 -1.2(3) . . . . ?
C6 C7 C8 C9 -0.2(2) . . . . ?
C5 C4 C9 C8 -2.67(19) . . . . ?
N1 C4 C9 C8 -179.13(12) . . . . ?
C5 C4 C9 C13 175.06(12) . . . . ?
N1 C4 C9 C13 -1.40(19) . . . . ?
C7 C8 C9 C4 2.1(2) . . . . ?
C7 C8 C9 C13 -175.65(14) . . . . ?
C6 C5 C10 C12 56.00(19) . . . . ?
C4 C5 C10 C12 -125.45(15) . . . . ?
C6 C5 C10 C11 -67.21(19) . . . . ?
C4 C5 C10 C11 111.34(17) . . . . ?
C4 C9 C13 C15 122.89(14) . . . . ?
C8 C9 C13 C15 -59.42(17) . . . . ?
C4 C9 C13 C14 -114.36(15) . . . . ?
C8 C9 C13 C14 63.33(18) . . . . ?
C1 N2 C16 C21 -58.27(16) . . . . ?
C3 N2 C16 C21 97.95(14) . . . . ?
C1 N2 C16 C17 127.34(13) . . . . ?
C3 N2 C16 C17 -76.44(14) . . . . ?
C21 C16 C17 C18 1.46(19) . . . . ?
N2 C16 C17 C18 175.69(12) . . . . ?
C21 C16 C17 C22 -179.24(12) . . . . ?
N2 C16 C17 C22 -5.01(18) . . . . ?
C16 C17 C18 C19 0.2(2) . . . . ?
C22 C17 C18 C19 -179.13(15) . . . . ?
C17 C18 C19 C20 -0.9(3) . . . . ?
C18 C19 C20 C21 -0.1(3) . . . . ?
C19 C20 C21 C16 1.7(2) . . . . ?
C19 C20 C21 C25 -176.70(15) . . . . ?
C17 C16 C21 C20 -2.4(2) . . . . ?
N2 C16 C21 C20 -176.53(12) . . . . ?
C17 C16 C21 C25 175.89(12) . . . . ?
N2 C16 C21 C25 1.73(19) . . . . ?
C18 C17 C22 C23 -67.42(17) . . . . ?
C16 C17 C22 C23 113.29(15) . . . . ?
C18 C17 C22 C24 55.61(18) . . . . ?
C16 C17 C22 C24 -123.68(14) . . . . ?
C20 C21 C25 C26 -59.18(17) . . . . ?
C16 C21 C25 C26 122.57(14) . . . . ?
C20 C21 C25 C27 64.94(17) . . . . ?
C16 C21 C25 C27 -113.31(14) . . . . ?
C31 Ni1 C28 F1 -102.50(9) . . . . ?
C1 Ni1 C28 F1 79.73(9) . . . . ?
O1 Ni1 C28 F1 -101.9(5) . . . . ?
C31 Ni1 C28 F2 137.55(10) . . . . ?
C1 Ni1 C28 F2 -40.21(10) . . . . ?
O1 Ni1 C28 F2 138.1(4) . . . . ?
C31 Ni1 C28 C29 14.47(9) . . . . ?
C1 Ni1 C28 C29 -163.30(9) . . . . ?
O1 Ni1 C28 C29 15.1(5) . . . . ?
F1 C28 C29 F4 -157.73(11) . . . . ?
F2 C28 C29 F4 -47.02(14) . . . . ?
Ni1 C28 C29 F4 81.30(12) . . . . ?
F1 C28 C29 F3 -38.61(14) . . . . ?
F2 C28 C29 F3 72.11(14) . . . . ?
Ni1 C28 C29 F3 -159.58(10) . . . . ?
F1 C28 C29 C30 85.24(12) . . . . ?
F2 C28 C29 C30 -164.05(11) . . . . ?
Ni1 C28 C29 C30 -35.73(13) . . . . ?
F4 C29 C30 F5 165.20(11) . . . . ?
F3 C29 C30 F5 48.75(15) . . . . ?
C28 C29 C30 F5 -76.46(13) . . . . ?
F4 C29 C30 F6 48.27(15) . . . . ?
F3 C29 C30 F6 -68.18(15) . . . . ?
C28 C29 C30 F6 166.61(11) . . . . ?
F4 C29 C30 C31 -76.76(13) . . . . ?
F3 C29 C30 C31 166.79(11) . . . . ?
C28 C29 C30 C31 41.58(13) . . . . ?
F5 C30 C31 F8 -152.65(11) . . . . ?
F6 C30 C31 F8 -32.31(15) . . . . ?
C29 C30 C31 F8 90.13(12) . . . . ?
F5 C30 C31 F7 -43.29(15) . . . . ?
F6 C30 C31 F7 77.06(14) . . . . ?
C29 C30 C31 F7 -160.51(10) . . . . ?
F5 C30 C31 Ni1 84.98(12) . . . . ?
F6 C30 C31 Ni1 -154.68(10) . . . . ?
C29 C30 C31 Ni1 -32.24(13) . . . . ?
C28 Ni1 C31 F8 -109.11(9) . . . . ?
C1 Ni1 C31 F8 -38.0(13) . . . . ?
O1 Ni1 C31 F8 70.95(9) . . . . ?
C28 Ni1 C31 F7 134.85(10) . . . . ?
C1 Ni1 C31 F7 -154.0(12) . . . . ?
O1 Ni1 C31 F7 -45.09(10) . . . . ?
C28 Ni1 C31 C30 10.51(9) . . . . ?
C1 Ni1 C31 C30 81.6(13) . . . . ?
O1 Ni1 C31 C30 -169.43(9) . . . . ?
C37 C32 C33 C34 -1.1(4) . . . . ?
C32 C33 C34 C35 1.5(4) . . . . ?
C33 C34 C35 C36 -0.3(5) . . . . ?
C34 C35 C36 C37 -1.2(5) . . . . ?
C35 C36 C37 C32 1.6(4) . . . . ?
C33 C32 C37 C36 -0.5(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_theta_full        28.36
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         0.360
_refine_diff_density_min         -0.283
_refine_diff_density_rms         0.045
