# Electronic Supplementary Material (ESI) for ChemComm.
# 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_l18913
_database_code_depnum_ccdc_archive 'CCDC 1036406'
_audit_update_record             
;
2014-11-26 deposited with the CCDC.
2015-01-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H20 F6 N4 Ni, F6 P'
_chemical_formula_sum            'C18 H20 F12 N4 Ni P'
_chemical_formula_weight         610.06

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'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           63
_space_group_name_H-M_alt        'C m c m'
_space_group_name_Hall           '-C 2c 2'

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

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

_cell_length_a                   10.3657(9)
_cell_length_b                   13.2968(11)
_cell_length_c                   16.2518(14)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2240.0(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4363
_cell_measurement_theta_min      2.51
_cell_measurement_theta_max      24.90

_exptl_crystal_description       rod
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.809
_exptl_crystal_F_000             1228
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.499
_exptl_crystal_size_mid          0.066
_exptl_crystal_size_min          0.042
_exptl_absorpt_coefficient_mu    1.053
_shelx_estimated_absorpt_T_min   0.622
_shelx_estimated_absorpt_T_max   0.957
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6661
_exptl_absorpt_correction_T_max  0.8620
_exptl_absorpt_process_details   'sadabs v2012/1'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(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            13318
_diffrn_reflns_av_unetI/netI     0.0243
_diffrn_reflns_av_R_equivalents  0.0477
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.491
_diffrn_reflns_theta_max         25.417
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             1136
_reflns_number_gt                946
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT-2013 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
  
All  H atoms were positioned geometrically and refined using a 
riding model with C---H = 0.95--0.99 Å and with Uiso(H) 
= 1.2 (1.5 for methyl groups) times Ueq(C). 
  
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1485P)²+16.0909P] 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         1136
_refine_ls_number_parameters     117
_refine_ls_number_restraints     214
_refine_ls_R_factor_all          0.1004
_refine_ls_R_factor_gt           0.0859
_refine_ls_wR_factor_ref         0.2561
_refine_ls_wR_factor_gt          0.2402
_refine_ls_goodness_of_fit_ref   1.100
_refine_ls_restrained_S_all      1.048
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Ni1 Ni 0.0000 0.07362(11) 0.2500 0.0395(6) Uani 1 4 d S TU P . .
N1 N 0.0000 -0.0356(6) 0.1688(4) 0.0423(15) Uani 1 2 d S TU P B .
N2 N -0.2088(7) 0.0393(7) 0.2500 0.0559(18) Uani 1 2 d S TU P B .
C1 C -0.1118(8) -0.0757(6) 0.1476(5) 0.0644(14) Uani 1 1 d . U . . .
C2 C -0.1132(9) -0.1630(6) 0.0999(5) 0.073(2) Uani 1 1 d . U . . .
H2 H -0.1926 -0.1931 0.0841 0.088 Uiso 1 1 calc R U . . .
C3 C 0.0000 -0.2036(10) 0.0767(7) 0.080(3) Uani 1 2 d S TU P . .
H3 H 0.0000 -0.2622 0.0433 0.096 Uiso 1 2 calc R U P . .
C4 C -0.2297(7) -0.0200(6) 0.1746(4) 0.0644(14) Uani 1 1 d . U . . .
H4A H -0.2575 0.0256 0.1299 0.077 Uiso 1 1 calc R U . B .
H4B H -0.3002 -0.0688 0.1844 0.077 Uiso 1 1 calc R U . . .
C5 C -0.3047(11) 0.1205(10) 0.2500 0.081(3) Uani 1 2 d S TU P . .
H5A H -0.3142 0.1470 0.1941 0.121 Uiso 0.5 1 calc R U P A -1
H5B H -0.2761 0.1744 0.2868 0.121 Uiso 0.5 1 calc R U P A -1
H5C H -0.3878 0.0942 0.2691 0.121 Uiso 0.5 1 calc R U P A -1
C6 C 0.0165(15) 0.1817(12) 0.3264(11) 0.053(3) Uani 0.25 1 d D U P B -1
F1 F 0.0841(19) 0.1485(17) 0.3941(13) 0.057(3) Uani 0.25 1 d D U P B -1
F2 F 0.0867(19) 0.2592(13) 0.2939(11) 0.070(3) Uani 0.25 1 d D U P B -1
F3 F -0.0955(15) 0.2219(13) 0.3566(11) 0.055(3) Uani 0.25 1 d D U P B -1
C6' C 0.0169(16) 0.1694(12) 0.1546(11) 0.053(3) Uani 0.25 1 d D U P B -2
F1' F -0.1014(15) 0.1918(14) 0.1216(11) 0.057(3) Uani 0.25 1 d D U P B -2
F2' F 0.089(2) 0.1317(17) 0.0909(14) 0.070(3) Uani 0.25 1 d D U P B -2
F3' F 0.0723(16) 0.2590(12) 0.1767(10) 0.055(3) Uani 0.25 1 d D U P B -2
P1 P -0.5000 0.0000 0.0000 0.0527(10) Uani 1 4 d DS TU P . .
F4 F -0.5000 0.0238(8) 0.0935(4) 0.096(3) Uani 1 2 d DS TU P . .
F5 F -0.3896(5) 0.0798(4) -0.0079(4) 0.0930(18) Uani 1 1 d D U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ni1 C6 1.91(2) . ?
Ni1 N1 1.962(7) . ?
Ni1 N1 1.962(7) 10_556 ?
Ni1 C6' 2.014(19) . ?
Ni1 N2 2.212(8) . ?
Ni1 N2 2.212(8) 3 ?
N1 C1 1.322(8) 12 ?
N1 C1 1.322(8) . ?
N2 C5 1.467(14) . ?
N2 C4 1.473(8) . ?
N2 C4 1.473(8) 10_556 ?
C1 C2 1.395(11) . ?
C1 C4 1.495(11) . ?
C2 C3 1.346(11) . ?
C2 H2 0.9500 . ?
C3 C2 1.346(11) 12 ?
C3 H3 0.9500 . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 F2 1.368(9) . ?
C6 F3 1.370(9) . ?
C6 F1 1.378(9) . ?
C6' F3' 1.370(9) . ?
C6' F1' 1.371(9) . ?
C6' F2' 1.374(9) . ?
P1 F4 1.552(6) 9_455 ?
P1 F4 1.552(6) . ?
P1 F5 1.565(5) . ?
P1 F5 1.565(5) 9_455 ?
P1 F5 1.565(5) 12_455 ?
P1 F5 1.565(5) 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
C6 Ni1 N1 174.7(5) . . ?
C6 Ni1 N1 96.9(4) . 10_556 ?
N1 Ni1 N1 84.6(4) . 10_556 ?
N1 Ni1 C6' 87.1(5) . . ?
N1 Ni1 C6' 170.3(5) 10_556 . ?
C6 Ni1 N2 104.1(5) . . ?
N1 Ni1 N2 81.23(18) . . ?
N1 Ni1 N2 81.23(18) 10_556 . ?
C6' Ni1 N2 102.4(5) . . ?
C6 Ni1 N2 93.9(5) . 3 ?
N1 Ni1 N2 81.23(17) . 3 ?
N1 Ni1 N2 81.23(17) 10_556 3 ?
C6' Ni1 N2 92.6(5) . 3 ?
N2 Ni1 N2 156.2(5) . 3 ?
C1 N1 C1 122.6(9) 12 . ?
C1 N1 Ni1 118.3(4) 12 . ?
C1 N1 Ni1 118.3(4) . . ?
C5 N2 C4 107.1(5) . . ?
C5 N2 C4 107.1(5) . 10_556 ?
C4 N2 C4 112.5(8) . 10_556 ?
C5 N2 Ni1 120.8(7) . . ?
C4 N2 Ni1 104.7(4) . . ?
C4 N2 Ni1 104.7(4) 10_556 . ?
N1 C1 C2 119.3(8) . . ?
N1 C1 C4 116.1(6) . . ?
C2 C1 C4 124.5(7) . . ?
C3 C2 C1 118.7(9) . . ?
C3 C2 H2 120.6 . . ?
C1 C2 H2 120.6 . . ?
C2 C3 C2 121.3(11) 12 . ?
C2 C3 H3 119.3 12 . ?
C2 C3 H3 119.3 . . ?
N2 C4 C1 112.9(6) . . ?
N2 C4 H4A 109.0 . . ?
C1 C4 H4A 109.0 . . ?
N2 C4 H4B 109.0 . . ?
C1 C4 H4B 109.0 . . ?
H4A C4 H4B 107.8 . . ?
N2 C5 H5A 109.5 . . ?
N2 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
N2 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
F2 C6 F3 107.2(11) . . ?
F2 C6 F1 106.2(11) . . ?
F3 C6 F1 105.6(11) . . ?
F2 C6 Ni1 111.4(13) . . ?
F3 C6 Ni1 116.9(12) . . ?
F1 C6 Ni1 109.0(13) . . ?
F3' C6' F1' 106.8(11) . . ?
F3' C6' F2' 106.6(11) . . ?
F1' C6' F2' 105.8(11) . . ?
F3' C6' Ni1 112.6(11) . . ?
F1' C6' Ni1 111.1(12) . . ?
F2' C6' Ni1 113.4(13) . . ?
F4 P1 F4 180.0 9_455 . ?
F4 P1 F5 93.3(4) 9_455 . ?
F4 P1 F5 86.7(4) . . ?
F4 P1 F5 86.7(4) 9_455 9_455 ?
F4 P1 F5 93.3(4) . 9_455 ?
F5 P1 F5 180.0 . 9_455 ?
F4 P1 F5 93.3(4) 9_455 12_455 ?
F4 P1 F5 86.7(4) . 12_455 ?
F5 P1 F5 93.9(4) . 12_455 ?
F5 P1 F5 86.1(4) 9_455 12_455 ?
F4 P1 F5 86.7(4) 9_455 4 ?
F4 P1 F5 93.3(4) . 4 ?
F5 P1 F5 86.1(4) . 4 ?
F5 P1 F5 93.9(4) 9_455 4 ?
F5 P1 F5 180.0(6) 12_455 4 ?

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 N1 C1 C2 -1.1(15) 12 . . . ?
Ni1 N1 C1 C2 -170.3(6) . . . . ?
C1 N1 C1 C4 -178.6(5) 12 . . . ?
Ni1 N1 C1 C4 12.2(9) . . . . ?
N1 C1 C2 C3 -0.1(13) . . . . ?
C4 C1 C2 C3 177.2(9) . . . . ?
C1 C2 C3 C2 1.3(18) . . . 12 ?
C5 N2 C4 C1 155.9(7) . . . . ?
C4 N2 C4 C1 -86.6(8) 10_556 . . . ?
Ni1 N2 C4 C1 26.6(8) . . . . ?
N1 C1 C4 N2 -27.6(10) . . . . ?
C2 C1 C4 N2 155.1(8) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
# C4 H4A F1'  0.99 2.74 3.23(2) 111.0 . 
# C4 H4A F4  0.99 2.58 3.151(8) 116.5 . 
# C4 H4B F2  0.99 2.59 3.535(19) 158.9 14_446 
# C5 H5A F3  0.98 2.61 3.09(2) 110.0 10_556 
C5 H5B F2 0.98 2.27 3.00(2) 131.1 12
C5 H5B F3 0.98 2.28 3.09(2) 139.1 .

_refine_diff_density_max         1.298
_refine_diff_density_min         -0.724
_refine_diff_density_rms         0.130

_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_l11513
_database_code_depnum_ccdc_archive 'CCDC 1036407'
_audit_update_record             
;
2014-11-26 deposited with the CCDC.
2015-01-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C24 H32 F6 N4 Ni), 0.25(C20 H48)'
_chemical_formula_sum            'C53 H76 F12 N8 Ni2'
_chemical_formula_weight         1170.63

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

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

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

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

_cell_length_a                   10.2621(5)
_cell_length_b                   19.5073(8)
_cell_length_c                   13.4730(6)
_cell_angle_alpha                90
_cell_angle_beta                 96.154(3)
_cell_angle_gamma                90
_cell_volume                     2681.6(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    7034
_cell_measurement_theta_min      2.58
_cell_measurement_theta_max      25.38

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.450
_exptl_crystal_F_000             1228
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.274
_exptl_crystal_size_mid          0.161
_exptl_crystal_size_min          0.057
_exptl_absorpt_coefficient_mu    0.788
_shelx_estimated_absorpt_T_min   0.813
_shelx_estimated_absorpt_T_max   0.956
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6552
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_process_details   'sadabs v2012/1'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(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            41249
_diffrn_reflns_av_unetI/netI     0.0429
_diffrn_reflns_av_R_equivalents  0.0726
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.844
_diffrn_reflns_theta_max         25.452
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4944
_reflns_number_gt                3753
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
  
All  H atoms were positioned geometrically and refined using a 
riding model with C---H = 0.95--0.99 Å and with Uiso(H) 
= 1.2 (1.5 for methyl groups) times Ueq(C). 
  
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0353P)²+2.4079P] 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         4944
_refine_ls_number_parameters     368
_refine_ls_number_restraints     168
_refine_ls_R_factor_all          0.0610
_refine_ls_R_factor_gt           0.0384
_refine_ls_wR_factor_ref         0.0905
_refine_ls_wR_factor_gt          0.0816
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_restrained_S_all      1.077
_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 0.26705(3) 0.15950(2) 0.31682(2) 0.01666(10) Uani 1 1 d . . . . .
F1 F 0.29253(18) 0.28058(8) 0.20780(12) 0.0365(4) Uani 1 1 d D U . . .
F2 F 0.14056(17) 0.28568(8) 0.30284(15) 0.0443(5) Uani 1 1 d D U . . .
F3 F 0.3384(2) 0.29400(8) 0.36437(13) 0.0480(5) Uani 1 1 d D U . . .
F4 F 0.5232(3) 0.2163(2) 0.3368(4) 0.0375(18) Uani 0.463(8) 1 d D U P A 1
F5 F 0.5242(4) 0.1082(2) 0.3251(5) 0.0395(19) Uani 0.463(8) 1 d D U P A 1
F6 F 0.4723(6) 0.1696(4) 0.1962(3) 0.0451(18) Uani 0.463(8) 1 d D U P A 1
F4' F 0.5309(3) 0.1643(3) 0.3744(3) 0.056(2) Uani 0.537(8) 1 d D U P A 2
F5' F 0.4855(5) 0.09583(18) 0.2533(6) 0.0558(19) Uani 0.537(8) 1 d D U P A 2
F6' F 0.4918(6) 0.2016(3) 0.2241(5) 0.0519(18) Uani 0.537(8) 1 d D U P A 2
N1 N 0.2789(2) 0.06252(10) 0.34790(15) 0.0170(5) Uani 1 1 d . . . . .
N2 N 0.0893(2) 0.15665(10) 0.36385(15) 0.0163(5) Uani 1 1 d . . . . .
N3 N 0.1273(2) 0.10533(11) 0.17088(15) 0.0197(5) Uani 1 1 d . . . . .
N4 N 0.2327(2) 0.12069(10) 0.56496(15) 0.0190(5) Uani 1 1 d . . . . .
C1 C 0.3160(2) 0.04076(13) 0.44186(19) 0.0179(6) Uani 1 1 d . . . . .
C2 C 0.3258(3) -0.02877(13) 0.4631(2) 0.0228(6) Uani 1 1 d . . . . .
H2 H 0.3538 -0.0438 0.5291 0.027 Uiso 1 1 calc R U . . .
C3 C 0.2947(3) -0.07605(13) 0.3880(2) 0.0253(6) Uani 1 1 d . . . . .
H3 H 0.3017 -0.1237 0.4018 0.030 Uiso 1 1 calc R U . . .
C4 C 0.2537(3) -0.05356(13) 0.2930(2) 0.0235(6) Uani 1 1 d . . . . .
H4 H 0.2301 -0.0855 0.2409 0.028 Uiso 1 1 calc R U . . .
C5 C 0.2471(3) 0.01633(13) 0.27441(19) 0.0187(6) Uani 1 1 d . . . . .
C6 C 0.2089(3) 0.04326(13) 0.17095(19) 0.0232(6) Uani 1 1 d . . . . .
H6A H 0.2891 0.0538 0.1391 0.028 Uiso 1 1 calc R U . . .
H6B H 0.1600 0.0073 0.1307 0.028 Uiso 1 1 calc R U . . .
C7 C 0.0063(3) 0.09117(13) 0.21584(19) 0.0203(6) Uani 1 1 d . . . . .
H7A H 0.0077 0.0428 0.2380 0.024 Uiso 1 1 calc R U . . .
H7B H -0.0689 0.0967 0.1640 0.024 Uiso 1 1 calc R U . . .
C8 C -0.0155(3) 0.13615(13) 0.30323(19) 0.0190(6) Uani 1 1 d . . . . .
C9 C -0.1426(3) 0.14891(13) 0.3257(2) 0.0238(6) Uani 1 1 d . . . . .
H9 H -0.2159 0.1353 0.2810 0.029 Uiso 1 1 calc R U . . .
C10 C -0.1603(3) 0.18160(14) 0.4139(2) 0.0275(7) Uani 1 1 d . . . . .
H10 H -0.2459 0.1934 0.4290 0.033 Uiso 1 1 calc R U . . .
C11 C -0.0521(3) 0.19706(14) 0.4799(2) 0.0273(7) Uani 1 1 d . . . . .
H11 H -0.0629 0.2171 0.5428 0.033 Uiso 1 1 calc R U . . .
C12 C 0.0719(3) 0.18318(13) 0.45426(19) 0.0199(6) Uani 1 1 d . . . . .
C13 C 0.1919(3) 0.18959(13) 0.5282(2) 0.0215(6) Uani 1 1 d . . . . .
H13A H 0.2636 0.2113 0.4959 0.026 Uiso 1 1 calc R U . . .
H13B H 0.1723 0.2188 0.5848 0.026 Uiso 1 1 calc R U . . .
C14 C 0.3483(3) 0.09456(13) 0.52175(19) 0.0189(6) Uani 1 1 d . . . . .
H14A H 0.4098 0.0746 0.5757 0.023 Uiso 1 1 calc R U . . .
H14B H 0.3933 0.1334 0.4926 0.023 Uiso 1 1 calc R U . . .
C15 C 0.1021(3) 0.13900(13) 0.07013(19) 0.0228(6) Uani 1 1 d . . . . .
C16 C 0.2318(3) 0.16120(15) 0.0345(2) 0.0338(7) Uani 1 1 d . . . . .
H16A H 0.2805 0.1895 0.0860 0.051 Uiso 1 1 calc R U . . .
H16B H 0.2146 0.1878 -0.0271 0.051 Uiso 1 1 calc R U . . .
H16C H 0.2836 0.1205 0.0219 0.051 Uiso 1 1 calc R U . . .
C17 C 0.0314(3) 0.09163(14) -0.0085(2) 0.0295(7) Uani 1 1 d . . . . .
H17A H 0.0889 0.0532 -0.0212 0.044 Uiso 1 1 calc R U . . .
H17B H 0.0087 0.1173 -0.0704 0.044 Uiso 1 1 calc R U . . .
H17C H -0.0488 0.0740 0.0159 0.044 Uiso 1 1 calc R U . . .
C18 C 0.0189(3) 0.20317(14) 0.0815(2) 0.0291(7) Uani 1 1 d . . . . .
H18A H -0.0688 0.1896 0.0964 0.044 Uiso 1 1 calc R U . . .
H18B H 0.0119 0.2295 0.0192 0.044 Uiso 1 1 calc R U . . .
H18C H 0.0604 0.2315 0.1360 0.044 Uiso 1 1 calc R U . . .
C19 C 0.2336(3) 0.11058(14) 0.6750(2) 0.0276(6) Uani 1 1 d . . . . .
C20 C 0.0978(3) 0.12813(18) 0.7045(2) 0.0422(8) Uani 1 1 d . . . . .
H20A H 0.0837 0.1777 0.6989 0.063 Uiso 1 1 calc R U . . .
H20B H 0.0918 0.1136 0.7735 0.063 Uiso 1 1 calc R U . . .
H20C H 0.0309 0.1043 0.6599 0.063 Uiso 1 1 calc R U . . .
C21 C 0.3385(3) 0.15407(16) 0.7345(2) 0.0377(8) Uani 1 1 d . . . . .
H21A H 0.4251 0.1412 0.7163 0.056 Uiso 1 1 calc R U . . .
H21B H 0.3353 0.1462 0.8061 0.056 Uiso 1 1 calc R U . . .
H21C H 0.3223 0.2027 0.7194 0.056 Uiso 1 1 calc R U . . .
C22 C 0.2576(3) 0.03471(15) 0.6999(2) 0.0344(8) Uani 1 1 d . . . . .
H22A H 0.1981 0.0065 0.6552 0.052 Uiso 1 1 calc R U . . .
H22B H 0.2417 0.0261 0.7692 0.052 Uiso 1 1 calc R U . . .
H22C H 0.3485 0.0229 0.6911 0.052 Uiso 1 1 calc R U . . .
C23 C 0.2603(3) 0.25620(14) 0.29752(18) 0.0224(6) Uani 1 1 d D . . . .
C24 C 0.4471(3) 0.16050(13) 0.29140(18) 0.0271(6) Uani 1 1 d D . . . .
C1S C 0.1535(16) 0.3894(7) 0.5378(13) 0.0450(12) Uani 0.25 1 d DG U P B -1
H1S1 H 0.1774 0.3468 0.5056 0.068 Uiso 0.25 1 calc R U P B -1
H1S2 H 0.1150 0.3785 0.5994 0.068 Uiso 0.25 1 calc R U P B -1
H1S3 H 0.2321 0.4175 0.5537 0.068 Uiso 0.25 1 calc R U P B -1
C2S C 0.0537(14) 0.4290(6) 0.4669(10) 0.0450(12) Uani 0.25 1 d DG U P B -1
H2S1 H -0.0270 0.4013 0.4524 0.054 Uiso 0.25 1 calc R U P B -1
H2S2 H 0.0904 0.4377 0.4030 0.054 Uiso 0.25 1 calc R U P B -1
C3S C 0.0179(12) 0.5019(6) 0.5176(10) 0.0450(12) Uani 0.25 1 d DG U P B -1
H3S1 H -0.0166 0.4934 0.5823 0.054 Uiso 0.25 1 calc R U P B -1
H3S2 H 0.0979 0.5304 0.5300 0.054 Uiso 0.25 1 calc R U P B -1
C4S C -0.0807(12) 0.5379(7) 0.4498(10) 0.0450(12) Uani 0.25 1 d DG U P B -1
H4S1 H -0.1618 0.5103 0.4382 0.054 Uiso 0.25 1 calc R U P B -1
H4S2 H -0.0471 0.5466 0.3848 0.054 Uiso 0.25 1 calc R U P B -1
C5S C -0.1093(16) 0.6090(7) 0.5036(15) 0.0450(12) Uani 0.25 1 d DG U P B -1
H5S1 H -0.1750 0.6352 0.4611 0.068 Uiso 0.25 1 calc R U P B -1
H5S2 H -0.0281 0.6357 0.5147 0.068 Uiso 0.25 1 calc R U P B -1
H5S3 H -0.1422 0.5996 0.5679 0.068 Uiso 0.25 1 calc R U P B -1
C1S' C 0.1449(15) 0.3925(8) 0.4999(16) 0.0450(12) Uani 0.25 1 d DG U P C -2
H1S4 H 0.2224 0.3717 0.5370 0.068 Uiso 0.25 1 calc R U P C -2
H1S5 H 0.1605 0.3985 0.4300 0.068 Uiso 0.25 1 calc R U P C -2
H1S6 H 0.0690 0.3625 0.5036 0.068 Uiso 0.25 1 calc R U P C -2
C2S' C 0.1184(10) 0.4619(7) 0.5453(10) 0.0450(12) Uani 0.25 1 d DG U P C -2
H2S3 H 0.1970 0.4913 0.5449 0.054 Uiso 0.25 1 calc R U P C -2
H2S4 H 0.1008 0.4556 0.6156 0.054 Uiso 0.25 1 calc R U P C -2
C3S' C -0.0072(12) 0.4998(7) 0.4829(10) 0.0450(12) Uani 0.25 1 d DG U P C -2
H3S3 H 0.0170 0.5155 0.4175 0.054 Uiso 0.25 1 calc R U P C -2
H3S4 H -0.0809 0.4671 0.4708 0.054 Uiso 0.25 1 calc R U P C -2
C4S' C -0.0481(13) 0.5595(6) 0.5408(10) 0.0450(12) Uani 0.25 1 d DG U P C -2
H4S3 H 0.0243 0.5930 0.5531 0.054 Uiso 0.25 1 calc R U P C -2
H4S4 H -0.0754 0.5446 0.6057 0.054 Uiso 0.25 1 calc R U P C -2
C5S' C -0.1693(14) 0.5922(7) 0.4715(13) 0.0450(12) Uani 0.25 1 d DG U P C -2
H5S4 H -0.2022 0.6323 0.5049 0.068 Uiso 0.25 1 calc R U P C -2
H5S5 H -0.2393 0.5580 0.4598 0.068 Uiso 0.25 1 calc R U P C -2
H5S6 H -0.1403 0.6062 0.4075 0.068 Uiso 0.25 1 calc R U P C -2


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ni1 C23 1.905(3) . ?
Ni1 C24 1.915(3) . ?
Ni1 N1 1.939(2) . ?
Ni1 N2 1.994(2) . ?
F1 C23 1.372(3) . ?
F2 C23 1.365(3) . ?
F3 C23 1.358(3) . ?
F4 C24 1.437(4) . ?
F5 C24 1.341(4) . ?
F6 C24 1.348(5) . ?
F4' C24 1.338(4) . ?
F5' C24 1.433(4) . ?
F6' C24 1.328(5) . ?
N1 C1 1.351(3) . ?
N1 C5 1.352(3) . ?
N2 C8 1.340(3) . ?
N2 C12 1.353(3) . ?
N3 C7 1.466(3) . ?
N3 C6 1.472(3) . ?
N3 C15 1.505(3) . ?
N4 C14 1.468(3) . ?
N4 C13 1.477(3) . ?
N4 C19 1.495(3) . ?
C1 C2 1.388(3) . ?
C1 C14 1.514(3) . ?
C2 C3 1.381(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.375(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.387(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.502(4) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.504(4) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.393(4) . ?
C9 C10 1.377(4) . ?
C9 H9 0.9500 . ?
C10 C11 1.380(4) . ?
C10 H10 0.9500 . ?
C11 C12 1.381(4) . ?
C11 H11 0.9500 . ?
C12 C13 1.504(4) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.525(4) . ?
C15 C17 1.529(4) . ?
C15 C18 1.532(4) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 C20 1.528(4) . ?
C19 C21 1.528(4) . ?
C19 C22 1.532(4) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C1S C2S 1.5333 . ?
C1S H1S1 0.9800 . ?
C1S H1S2 0.9800 . ?
C1S H1S3 0.9800 . ?
C2S C3S 1.6368 . ?
C2S H2S1 0.9900 . ?
C2S H2S2 0.9900 . ?
C3S C4S 1.4675 . ?
C3S H3S1 0.9900 . ?
C3S H3S2 0.9900 . ?
C4S C5S 1.6066 . ?
C4S H4S1 0.9900 . ?
C4S H4S2 0.9900 . ?
C5S H5S1 0.9800 . ?
C5S H5S2 0.9800 . ?
C5S H5S3 0.9800 . ?
C1S' C2S' 1.5229 . ?
C1S' H1S4 0.9800 . ?
C1S' H1S5 0.9800 . ?
C1S' H1S6 0.9800 . ?
C2S' C3S' 1.6378 . ?
C2S' H2S3 0.9900 . ?
C2S' H2S4 0.9900 . ?
C3S' C4S' 1.4866 . ?
C3S' H3S3 0.9900 . ?
C3S' H3S4 0.9900 . ?
C4S' C5S' 1.6047 . ?
C4S' H4S3 0.9900 . ?
C4S' H4S4 0.9900 . ?
C5S' H5S4 0.9800 . ?
C5S' H5S5 0.9800 . ?
C5S' H5S6 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C23 Ni1 C24 89.27(11) . . ?
C23 Ni1 N1 175.28(10) . . ?
C24 Ni1 N1 90.53(10) . . ?
C23 Ni1 N2 92.85(10) . . ?
C24 Ni1 N2 171.76(10) . . ?
N1 Ni1 N2 86.71(8) . . ?
C1 N1 C5 119.9(2) . . ?
C1 N1 Ni1 120.93(17) . . ?
C5 N1 Ni1 119.16(17) . . ?
C8 N2 C12 119.2(2) . . ?
C8 N2 Ni1 121.08(17) . . ?
C12 N2 Ni1 119.29(17) . . ?
C7 N3 C6 110.6(2) . . ?
C7 N3 C15 112.6(2) . . ?
C6 N3 C15 113.7(2) . . ?
C14 N4 C13 113.3(2) . . ?
C14 N4 C19 115.4(2) . . ?
C13 N4 C19 115.1(2) . . ?
N1 C1 C2 120.5(2) . . ?
N1 C1 C14 117.8(2) . . ?
C2 C1 C14 121.7(2) . . ?
C3 C2 C1 119.7(2) . . ?
C3 C2 H2 120.2 . . ?
C1 C2 H2 120.2 . . ?
C4 C3 C2 119.5(2) . . ?
C4 C3 H3 120.3 . . ?
C2 C3 H3 120.3 . . ?
C3 C4 C5 119.1(2) . . ?
C3 C4 H4 120.5 . . ?
C5 C4 H4 120.5 . . ?
N1 C5 C4 121.3(2) . . ?
N1 C5 C6 117.7(2) . . ?
C4 C5 C6 121.0(2) . . ?
N3 C6 C5 112.4(2) . . ?
N3 C6 H6A 109.1 . . ?
C5 C6 H6A 109.1 . . ?
N3 C6 H6B 109.1 . . ?
C5 C6 H6B 109.1 . . ?
H6A C6 H6B 107.9 . . ?
N3 C7 C8 114.7(2) . . ?
N3 C7 H7A 108.6 . . ?
C8 C7 H7A 108.6 . . ?
N3 C7 H7B 108.6 . . ?
C8 C7 H7B 108.6 . . ?
H7A C7 H7B 107.6 . . ?
N2 C8 C9 121.5(2) . . ?
N2 C8 C7 118.3(2) . . ?
C9 C8 C7 119.7(2) . . ?
C10 C9 C8 118.9(3) . . ?
C10 C9 H9 120.5 . . ?
C8 C9 H9 120.5 . . ?
C9 C10 C11 119.1(3) . . ?
C9 C10 H10 120.5 . . ?
C11 C10 H10 120.5 . . ?
C10 C11 C12 119.7(3) . . ?
C10 C11 H11 120.2 . . ?
C12 C11 H11 120.2 . . ?
N2 C12 C11 121.0(2) . . ?
N2 C12 C13 116.8(2) . . ?
C11 C12 C13 121.9(2) . . ?
N4 C13 C12 109.2(2) . . ?
N4 C13 H13A 109.8 . . ?
C12 C13 H13A 109.8 . . ?
N4 C13 H13B 109.8 . . ?
C12 C13 H13B 109.8 . . ?
H13A C13 H13B 108.3 . . ?
N4 C14 C1 113.5(2) . . ?
N4 C14 H14A 108.9 . . ?
C1 C14 H14A 108.9 . . ?
N4 C14 H14B 108.9 . . ?
C1 C14 H14B 108.9 . . ?
H14A C14 H14B 107.7 . . ?
N3 C15 C16 109.6(2) . . ?
N3 C15 C17 112.6(2) . . ?
C16 C15 C17 108.6(2) . . ?
N3 C15 C18 108.1(2) . . ?
C16 C15 C18 108.3(2) . . ?
C17 C15 C18 109.5(2) . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C15 C17 H17A 109.5 . . ?
C15 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C15 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C15 C18 H18A 109.5 . . ?
C15 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C15 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
N4 C19 C20 108.6(2) . . ?
N4 C19 C21 112.1(2) . . ?
C20 C19 C21 110.5(3) . . ?
N4 C19 C22 109.1(2) . . ?
C20 C19 C22 106.9(2) . . ?
C21 C19 C22 109.5(3) . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C19 C21 H21A 109.5 . . ?
C19 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C19 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C19 C22 H22A 109.5 . . ?
C19 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C19 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
F3 C23 F2 102.0(2) . . ?
F3 C23 F1 102.4(2) . . ?
F2 C23 F1 101.8(2) . . ?
F3 C23 Ni1 115.93(17) . . ?
F2 C23 Ni1 115.46(17) . . ?
F1 C23 Ni1 117.05(17) . . ?
F6' C24 F4' 107.4(4) . . ?
F5 C24 F6 104.8(4) . . ?
F6' C24 F5' 99.1(3) . . ?
F4' C24 F5' 99.9(4) . . ?
F5 C24 F4 99.1(3) . . ?
F6 C24 F4 98.9(4) . . ?
F6' C24 Ni1 122.6(3) . . ?
F4' C24 Ni1 113.4(2) . . ?
F5 C24 Ni1 118.5(2) . . ?
F6 C24 Ni1 117.3(3) . . ?
F5' C24 Ni1 111.3(2) . . ?
F4 C24 Ni1 115.0(2) . . ?
C2S C1S H1S1 109.5 . . ?
C2S C1S H1S2 109.5 . . ?
H1S1 C1S H1S2 109.5 . . ?
C2S C1S H1S3 109.5 . . ?
H1S1 C1S H1S3 109.5 . . ?
H1S2 C1S H1S3 109.5 . . ?
C1S C2S C3S 110.0 . . ?
C1S C2S H2S1 109.7 . . ?
C3S C2S H2S1 109.7 . . ?
C1S C2S H2S2 109.7 . . ?
C3S C2S H2S2 109.7 . . ?
H2S1 C2S H2S2 108.2 . . ?
C4S C3S C2S 109.1 . . ?
C4S C3S H3S1 109.9 . . ?
C2S C3S H3S1 109.9 . . ?
C4S C3S H3S2 109.9 . . ?
C2S C3S H3S2 109.9 . . ?
H3S1 C3S H3S2 108.3 . . ?
C3S C4S C5S 106.3 . . ?
C3S C4S H4S1 110.5 . . ?
C5S C4S H4S1 110.5 . . ?
C3S C4S H4S2 110.5 . . ?
C5S C4S H4S2 110.5 . . ?
H4S1 C4S H4S2 108.7 . . ?
C4S C5S H5S1 109.5 . . ?
C4S C5S H5S2 109.5 . . ?
H5S1 C5S H5S2 109.5 . . ?
C4S C5S H5S3 109.5 . . ?
H5S1 C5S H5S3 109.5 . . ?
H5S2 C5S H5S3 109.5 . . ?
C2S' C1S' H1S4 109.5 . . ?
C2S' C1S' H1S5 109.5 . . ?
H1S4 C1S' H1S5 109.5 . . ?
C2S' C1S' H1S6 109.5 . . ?
H1S4 C1S' H1S6 109.5 . . ?
H1S5 C1S' H1S6 109.5 . . ?
C1S' C2S' C3S' 111.1 . . ?
C1S' C2S' H2S3 109.4 . . ?
C3S' C2S' H2S3 109.4 . . ?
C1S' C2S' H2S4 109.4 . . ?
C3S' C2S' H2S4 109.4 . . ?
H2S3 C2S' H2S4 108.0 . . ?
C4S' C3S' C2S' 109.6 . . ?
C4S' C3S' H3S3 109.8 . . ?
C2S' C3S' H3S3 109.8 . . ?
C4S' C3S' H3S4 109.8 . . ?
C2S' C3S' H3S4 109.8 . . ?
H3S3 C3S' H3S4 108.2 . . ?
C3S' C4S' C5S' 104.5 . . ?
C3S' C4S' H4S3 110.9 . . ?
C5S' C4S' H4S3 110.9 . . ?
C3S' C4S' H4S4 110.9 . . ?
C5S' C4S' H4S4 110.9 . . ?
H4S3 C4S' H4S4 108.9 . . ?
C4S' C5S' H5S4 109.5 . . ?
C4S' C5S' H5S5 109.5 . . ?
H5S4 C5S' H5S5 109.5 . . ?
C4S' C5S' H5S6 109.5 . . ?
H5S4 C5S' H5S6 109.5 . . ?
H5S5 C5S' H5S6 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 N1 C1 C2 2.1(4) . . . . ?
Ni1 N1 C1 C2 -179.16(19) . . . . ?
C5 N1 C1 C14 -179.0(2) . . . . ?
Ni1 N1 C1 C14 -0.2(3) . . . . ?
N1 C1 C2 C3 -1.4(4) . . . . ?
C14 C1 C2 C3 179.7(2) . . . . ?
C1 C2 C3 C4 -0.4(4) . . . . ?
C2 C3 C4 C5 1.4(4) . . . . ?
C1 N1 C5 C4 -1.0(4) . . . . ?
Ni1 N1 C5 C4 -179.81(19) . . . . ?
C1 N1 C5 C6 -178.9(2) . . . . ?
Ni1 N1 C5 C6 2.3(3) . . . . ?
C3 C4 C5 N1 -0.7(4) . . . . ?
C3 C4 C5 C6 177.1(2) . . . . ?
C7 N3 C6 C5 -59.9(3) . . . . ?
C15 N3 C6 C5 172.3(2) . . . . ?
N1 C5 C6 N3 -39.5(3) . . . . ?
C4 C5 C6 N3 142.6(2) . . . . ?
C6 N3 C7 C8 123.1(2) . . . . ?
C15 N3 C7 C8 -108.5(2) . . . . ?
C12 N2 C8 C9 7.8(3) . . . . ?
Ni1 N2 C8 C9 -164.58(18) . . . . ?
C12 N2 C8 C7 -164.8(2) . . . . ?
Ni1 N2 C8 C7 22.8(3) . . . . ?
N3 C7 C8 N2 -34.1(3) . . . . ?
N3 C7 C8 C9 153.2(2) . . . . ?
N2 C8 C9 C10 -1.9(4) . . . . ?
C7 C8 C9 C10 170.6(2) . . . . ?
C8 C9 C10 C11 -3.8(4) . . . . ?
C9 C10 C11 C12 3.7(4) . . . . ?
C8 N2 C12 C11 -7.9(4) . . . . ?
Ni1 N2 C12 C11 164.60(19) . . . . ?
C8 N2 C12 C13 165.8(2) . . . . ?
Ni1 N2 C12 C13 -21.7(3) . . . . ?
C10 C11 C12 N2 2.2(4) . . . . ?
C10 C11 C12 C13 -171.2(2) . . . . ?
C14 N4 C13 C12 104.5(2) . . . . ?
C19 N4 C13 C12 -119.7(2) . . . . ?
N2 C12 C13 N4 -72.4(3) . . . . ?
C11 C12 C13 N4 101.2(3) . . . . ?
C13 N4 C14 C1 -103.9(2) . . . . ?
C19 N4 C14 C1 120.5(2) . . . . ?
N1 C1 C14 N4 84.2(3) . . . . ?
C2 C1 C14 N4 -96.8(3) . . . . ?
C7 N3 C15 C16 172.1(2) . . . . ?
C6 N3 C15 C16 -61.1(3) . . . . ?
C7 N3 C15 C17 -66.8(3) . . . . ?
C6 N3 C15 C17 59.9(3) . . . . ?
C7 N3 C15 C18 54.3(3) . . . . ?
C6 N3 C15 C18 -179.0(2) . . . . ?
C14 N4 C19 C20 -169.7(2) . . . . ?
C13 N4 C19 C20 55.5(3) . . . . ?
C14 N4 C19 C21 68.0(3) . . . . ?
C13 N4 C19 C21 -66.8(3) . . . . ?
C14 N4 C19 C22 -53.5(3) . . . . ?
C13 N4 C19 C22 171.7(2) . . . . ?
C1S C2S C3S C4S -178.3 . . . . ?
C2S C3S C4S C5S -179.3 . . . . ?
C1S' C2S' C3S' C4S' 167.8 . . . . ?
C2S' C3S' C4S' C5S' 179.3 . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
# C13 H13A F3  0.99 2.57 3.463(3) 149.5 . 
# C18 H18B F3  0.98 2.63 3.290(3) 124.7 4_565 
C14 H14B F4' 0.99 2.32 3.179(5) 144.7 .
C2 H2 F5 0.95 2.55 3.459(5) 161.5 3_656
C18 H18C F2 0.98 2.54 3.500(3) 166.5 .
C6 H6A F5' 0.99 2.54 3.109(6) 116.6 .
C17 H17B F3 0.98 2.55 3.333(3) 137.1 4_565
C16 H16A F1 0.98 2.41 3.309(3) 151.7 .
C16 H16A F6 0.98 2.37 3.116(7) 132.7 .
# C20 H20A F6'  0.98 2.57 3.514(6) 161.3 4_566 

_refine_diff_density_max         0.724
_refine_diff_density_min         -0.407
_refine_diff_density_rms         0.061

_shelxl_version_number           2013-3

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

data_l11613
_database_code_depnum_ccdc_archive 'CCDC 1036408'
_audit_update_record             
;
2014-11-26 deposited with the CCDC.
2015-01-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H32 F6 N4 Ni, F6 P, C4 H8 O'
_chemical_formula_sum            'C28 H40 F12 N4 Ni O P'
_chemical_formula_weight         766.32

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'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   14.2479(13)
_cell_length_b                   14.4930(15)
_cell_length_c                   30.515(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     6301.2(11)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3310
_cell_measurement_theta_min      2.41
_cell_measurement_theta_max      18.70

_exptl_crystal_description       rod
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.616
_exptl_crystal_F_000             3160
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.241
_exptl_crystal_size_mid          0.239
_exptl_crystal_size_min          0.109
_exptl_absorpt_coefficient_mu    0.769
_shelx_estimated_absorpt_T_min   0.836
_shelx_estimated_absorpt_T_max   0.921
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6363
_exptl_absorpt_correction_T_max  0.7440
_exptl_absorpt_process_details   'sadabs v2012/1'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(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            123227
_diffrn_reflns_av_unetI/netI     0.1185
_diffrn_reflns_av_R_equivalents  0.3433
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_theta_min         1.956
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             5548
_reflns_number_gt                2636
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
  
All  H atoms were positioned geometrically and refined using a 
riding model with C---H = 0.95--0.99 Å and with Uiso(H) 
= 1.2 (1.5 for methyl groups) times Ueq(C). 
  
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0732P)²+16.0464P] 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         5548
_refine_ls_number_parameters     430
_refine_ls_number_restraints     46
_refine_ls_R_factor_all          0.1687
_refine_ls_R_factor_gt           0.0647
_refine_ls_wR_factor_ref         0.1906
_refine_ls_wR_factor_gt          0.1380
_refine_ls_goodness_of_fit_ref   1.006
_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_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 0.93147(6) 0.73787(6) 0.32917(3) 0.0305(3) Uani 1 1 d . . . . .
F1 F 0.9276(3) 0.5444(3) 0.31697(16) 0.0601(14) Uani 1 1 d . . . . .
F2 F 0.8289(4) 0.6165(3) 0.27601(16) 0.0683(15) Uani 1 1 d . . . . .
F3 F 0.7994(3) 0.5969(3) 0.34446(15) 0.0534(13) Uani 1 1 d . . . . .
F4 F 1.0957(3) 0.6435(3) 0.30781(15) 0.0530(13) Uani 1 1 d . . . . .
F5 F 1.0884(3) 0.7761(3) 0.27888(13) 0.0473(12) Uani 1 1 d . . . . .
F6 F 1.0099(3) 0.6636(3) 0.25163(15) 0.0628(14) Uani 1 1 d . . . . .
N1 N 0.9917(4) 0.8542(4) 0.34429(17) 0.0269(14) Uani 1 1 d . . . . .
N2 N 0.8261(4) 0.7716(4) 0.36521(17) 0.0280(13) Uani 1 1 d . . . . .
N3 N 0.8415(4) 0.8427(4) 0.28333(17) 0.0333(15) Uani 1 1 d . . . . .
N4 N 1.0008(4) 0.7066(4) 0.39928(17) 0.0286(14) Uani 1 1 d . . . . .
C1 C 1.0657(5) 0.8540(5) 0.3711(2) 0.0271(16) Uani 1 1 d . . . . .
C2 C 1.1167(5) 0.9334(5) 0.3780(2) 0.0342(18) Uani 1 1 d . . . . .
H2 H 1.1690 0.9329 0.3973 0.041 Uiso 1 1 calc R U . . .
C3 C 1.0913(5) 1.0137(5) 0.3566(2) 0.040(2) Uani 1 1 d . . . . .
H3 H 1.1281 1.0680 0.3597 0.048 Uiso 1 1 calc R U . . .
C4 C 1.0112(5) 1.0138(5) 0.3306(2) 0.0345(17) Uani 1 1 d . . . . .
H4 H 0.9913 1.0686 0.3162 0.041 Uiso 1 1 calc R U . . .
C5 C 0.9614(5) 0.9334(5) 0.3261(2) 0.0291(17) Uani 1 1 d . . . . .
C6 C 0.8657(5) 0.9310(5) 0.3049(2) 0.0354(18) Uani 1 1 d . . . . .
H6A H 0.8179 0.9443 0.3275 0.042 Uiso 1 1 calc R U . . .
H6B H 0.8625 0.9809 0.2827 0.042 Uiso 1 1 calc R U . . .
C7 C 0.7460(5) 0.8134(6) 0.2981(2) 0.0377(19) Uani 1 1 d . . . . .
H7A H 0.7277 0.7563 0.2824 0.045 Uiso 1 1 calc R U . . .
H7B H 0.6999 0.8620 0.2907 0.045 Uiso 1 1 calc R U . . .
C8 C 0.7442(5) 0.7960(5) 0.3469(2) 0.0315(17) Uani 1 1 d . . . . .
C9 C 0.6644(5) 0.8049(5) 0.3715(2) 0.0415(19) Uani 1 1 d . . . . .
H9 H 0.6070 0.8227 0.3582 0.050 Uiso 1 1 calc R U . . .
C10 C 0.6684(5) 0.7878(5) 0.4159(2) 0.042(2) Uani 1 1 d . . . . .
H10 H 0.6130 0.7893 0.4332 0.051 Uiso 1 1 calc R U . . .
C11 C 0.7552(5) 0.7681(5) 0.4349(2) 0.0377(19) Uani 1 1 d . . . . .
H11 H 0.7596 0.7580 0.4656 0.045 Uiso 1 1 calc R U . . .
C12 C 0.8346(4) 0.7632(5) 0.4091(2) 0.0309(17) Uani 1 1 d . . . . .
C13 C 0.9307(4) 0.7583(5) 0.42751(19) 0.0286(16) Uani 1 1 d . . . . .
H13A H 0.9276 0.7280 0.4565 0.034 Uiso 1 1 calc R U . . .
H13B H 0.9541 0.8219 0.4321 0.034 Uiso 1 1 calc R U . . .
C14 C 1.0865(4) 0.7650(5) 0.3939(2) 0.0299(16) Uani 1 1 d . . . . .
H14A H 1.1135 0.7783 0.4231 0.036 Uiso 1 1 calc R U . . .
H14B H 1.1339 0.7303 0.3768 0.036 Uiso 1 1 calc R U . . .
C15 C 0.8433(5) 0.8538(6) 0.2326(2) 0.043(2) Uani 1 1 d . . . . .
C16 C 0.8265(6) 0.7629(6) 0.2102(2) 0.048(2) Uani 1 1 d . . . . .
H16A H 0.8751 0.7188 0.2190 0.072 Uiso 1 1 calc R U . . .
H16B H 0.8286 0.7716 0.1784 0.072 Uiso 1 1 calc R U . . .
H16C H 0.7647 0.7390 0.2186 0.072 Uiso 1 1 calc R U . . .
C17 C 0.7703(5) 0.9242(6) 0.2170(2) 0.052(2) Uani 1 1 d . . . . .
H17A H 0.7072 0.9023 0.2245 0.078 Uiso 1 1 calc R U . . .
H17B H 0.7753 0.9317 0.1851 0.078 Uiso 1 1 calc R U . . .
H17C H 0.7817 0.9837 0.2313 0.078 Uiso 1 1 calc R U . . .
C18 C 0.9407(5) 0.8890(6) 0.2192(2) 0.053(2) Uani 1 1 d . . . . .
H18A H 0.9520 0.9494 0.2327 0.079 Uiso 1 1 calc R U . . .
H18B H 0.9436 0.8949 0.1872 0.079 Uiso 1 1 calc R U . . .
H18C H 0.9887 0.8453 0.2291 0.079 Uiso 1 1 calc R U . . .
C19 C 1.0269(5) 0.6152(5) 0.4213(2) 0.0338(18) Uani 1 1 d . . . . .
C20 C 1.0903(6) 0.5571(5) 0.3920(3) 0.050(2) Uani 1 1 d . . . . .
H20A H 1.0568 0.5412 0.3650 0.075 Uiso 1 1 calc R U . . .
H20B H 1.1081 0.5005 0.4075 0.075 Uiso 1 1 calc R U . . .
H20C H 1.1470 0.5923 0.3847 0.075 Uiso 1 1 calc R U . . .
C21 C 1.0788(5) 0.6306(6) 0.4648(2) 0.045(2) Uani 1 1 d . . . . .
H21A H 1.1394 0.6603 0.4591 0.068 Uiso 1 1 calc R U . . .
H21B H 1.0893 0.5711 0.4792 0.068 Uiso 1 1 calc R U . . .
H21C H 1.0410 0.6703 0.4839 0.068 Uiso 1 1 calc R U . . .
C22 C 0.9375(6) 0.5605(5) 0.4299(3) 0.048(2) Uani 1 1 d . . . . .
H22A H 0.9020 0.5897 0.4536 0.072 Uiso 1 1 calc R U . . .
H22B H 0.9539 0.4973 0.4383 0.072 Uiso 1 1 calc R U . . .
H22C H 0.8991 0.5593 0.4032 0.072 Uiso 1 1 calc R U . . .
C23 C 0.8717(6) 0.6187(6) 0.3156(3) 0.044(2) Uani 1 1 d . . . . .
C24 C 1.0347(5) 0.7031(6) 0.2906(2) 0.0397(19) Uani 1 1 d . . . . .
P1 P 0.36578(13) 0.76922(15) 0.42978(6) 0.0361(5) Uani 1 1 d . . . . .
F7 F 0.4188(4) 0.8510(4) 0.45265(18) 0.0831(18) Uani 1 1 d . . . . .
F8 F 0.4123(4) 0.7001(4) 0.46344(16) 0.0827(18) Uani 1 1 d . . . . .
F9 F 0.3092(3) 0.6870(3) 0.40744(15) 0.0600(14) Uani 1 1 d . . . . .
F10 F 0.3174(3) 0.8395(3) 0.39720(13) 0.0492(12) Uani 1 1 d . . . . .
F11 F 0.4482(3) 0.7525(4) 0.39636(16) 0.0820(19) Uani 1 1 d . . . . .
F12 F 0.2799(3) 0.7831(3) 0.46268(14) 0.0641(14) Uani 1 1 d . . . . .
O1S O 0.6150(5) 0.4806(5) 0.4288(3) 0.101(3) Uani 1 1 d . U . . .
C1S C 0.6996(9) 0.4974(11) 0.4474(6) 0.175(6) Uani 1 1 d . U . . .
H1S1 H 0.7327 0.5464 0.4309 0.210 Uiso 1 1 calc R U . . .
H1S2 H 0.7386 0.4409 0.4465 0.210 Uiso 1 1 calc R U . . .
C2S C 0.6853(7) 0.5272(7) 0.4941(4) 0.097(3) Uani 1 1 d . U . . .
H2SA H 0.7391 0.5633 0.5054 0.116 Uiso 1 1 calc R U . . .
H2SB H 0.6727 0.4744 0.5138 0.116 Uiso 1 1 calc R U . . .
C3S C 0.5994(6) 0.5863(7) 0.4872(3) 0.061(2) Uani 1 1 d . U . . .
H3SA H 0.6152 0.6527 0.4885 0.073 Uiso 1 1 calc R U . . .
H3SB H 0.5505 0.5726 0.5093 0.073 Uiso 1 1 calc R U . . .
C4S C 0.5679(9) 0.5582(7) 0.4416(3) 0.092(3) Uani 1 1 d . U . . .
H4S1 H 0.4995 0.5461 0.4416 0.110 Uiso 1 1 calc R U . . .
H4S2 H 0.5806 0.6089 0.4207 0.110 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ni1 N2 1.924(5) . ?
Ni1 N1 1.946(5) . ?
Ni1 C24 1.949(8) . ?
Ni1 C23 1.969(8) . ?
Ni1 N4 2.399(5) . ?
Ni1 N3 2.431(6) . ?
F1 C23 1.341(9) . ?
F2 C23 1.353(8) . ?
F3 C23 1.392(9) . ?
F4 C24 1.333(8) . ?
F5 C24 1.354(8) . ?
F6 C24 1.367(8) . ?
N1 C1 1.334(8) . ?
N1 C5 1.347(8) . ?
N2 C8 1.341(8) . ?
N2 C12 1.351(8) . ?
N3 C6 1.480(9) . ?
N3 C7 1.495(9) . ?
N3 C15 1.556(8) . ?
N4 C14 1.495(8) . ?
N4 C13 1.516(8) . ?
N4 C19 1.531(8) . ?
C1 C2 1.377(9) . ?
C1 C14 1.495(9) . ?
C2 C3 1.383(10) . ?
C2 H2 0.9500 . ?
C3 C4 1.391(10) . ?
C3 H3 0.9500 . ?
C4 C5 1.371(9) . ?
C4 H4 0.9500 . ?
C5 C6 1.509(9) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.511(9) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.369(9) . ?
C9 C10 1.377(10) . ?
C9 H9 0.9500 . ?
C10 C11 1.396(10) . ?
C10 H10 0.9500 . ?
C11 C12 1.381(9) . ?
C11 H11 0.9500 . ?
C12 C13 1.481(9) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.504(10) . ?
C15 C17 1.533(11) . ?
C15 C18 1.535(10) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 C22 1.523(10) . ?
C19 C20 1.525(10) . ?
C19 C21 1.536(10) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
P1 F7 1.569(5) . ?
P1 F11 1.574(5) . ?
P1 F10 1.581(4) . ?
P1 F8 1.581(5) . ?
P1 F9 1.592(5) . ?
P1 F12 1.596(5) . ?
O1S C1S 1.355(14) . ?
O1S C4S 1.366(11) . ?
C1S C2S 1.504(18) . ?
C1S H1S1 0.9900 . ?
C1S H1S2 0.9900 . ?
C2S C3S 1.507(12) . ?
C2S H2SA 0.9900 . ?
C2S H2SB 0.9900 . ?
C3S C4S 1.519(12) . ?
C3S H3SA 0.9900 . ?
C3S H3SB 0.9900 . ?
C4S H4S1 0.9900 . ?
C4S H4S2 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 Ni1 N1 89.3(2) . . ?
N2 Ni1 C24 177.6(3) . . ?
N1 Ni1 C24 92.0(3) . . ?
N2 Ni1 C23 90.3(3) . . ?
N1 Ni1 C23 178.3(3) . . ?
C24 Ni1 C23 88.4(3) . . ?
N2 Ni1 N4 81.9(2) . . ?
N1 Ni1 N4 76.8(2) . . ?
C24 Ni1 N4 100.3(2) . . ?
C23 Ni1 N4 101.5(3) . . ?
N2 Ni1 N3 76.0(2) . . ?
N1 Ni1 N3 80.1(2) . . ?
C24 Ni1 N3 102.3(3) . . ?
C23 Ni1 N3 101.5(3) . . ?
N4 Ni1 N3 148.03(19) . . ?
C1 N1 C5 120.5(6) . . ?
C1 N1 Ni1 119.5(5) . . ?
C5 N1 Ni1 120.0(4) . . ?
C8 N2 C12 121.0(6) . . ?
C8 N2 Ni1 120.5(4) . . ?
C12 N2 Ni1 118.3(4) . . ?
C6 N3 C7 108.9(6) . . ?
C6 N3 C15 110.4(6) . . ?
C7 N3 C15 110.1(5) . . ?
C6 N3 Ni1 99.3(4) . . ?
C7 N3 Ni1 97.4(4) . . ?
C15 N3 Ni1 128.9(5) . . ?
C14 N4 C13 108.7(5) . . ?
C14 N4 C19 109.8(5) . . ?
C13 N4 C19 109.7(5) . . ?
C14 N4 Ni1 97.5(4) . . ?
C13 N4 Ni1 98.2(3) . . ?
C19 N4 Ni1 130.9(4) . . ?
N1 C1 C2 120.6(6) . . ?
N1 C1 C14 116.3(6) . . ?
C2 C1 C14 123.0(6) . . ?
C1 C2 C3 119.5(7) . . ?
C1 C2 H2 120.2 . . ?
C3 C2 H2 120.2 . . ?
C2 C3 C4 119.0(7) . . ?
C2 C3 H3 120.5 . . ?
C4 C3 H3 120.5 . . ?
C5 C4 C3 118.8(7) . . ?
C5 C4 H4 120.6 . . ?
C3 C4 H4 120.6 . . ?
N1 C5 C4 121.2(6) . . ?
N1 C5 C6 116.5(6) . . ?
C4 C5 C6 122.0(6) . . ?
N3 C6 C5 114.9(6) . . ?
N3 C6 H6A 108.5 . . ?
C5 C6 H6A 108.5 . . ?
N3 C6 H6B 108.5 . . ?
C5 C6 H6B 108.5 . . ?
H6A C6 H6B 107.5 . . ?
N3 C7 C8 111.1(5) . . ?
N3 C7 H7A 109.4 . . ?
C8 C7 H7A 109.4 . . ?
N3 C7 H7B 109.4 . . ?
C8 C7 H7B 109.4 . . ?
H7A C7 H7B 108.0 . . ?
N2 C8 C9 121.2(6) . . ?
N2 C8 C7 116.1(6) . . ?
C9 C8 C7 122.7(7) . . ?
C8 C9 C10 119.3(7) . . ?
C8 C9 H9 120.4 . . ?
C10 C9 H9 120.4 . . ?
C9 C10 C11 118.8(7) . . ?
C9 C10 H10 120.6 . . ?
C11 C10 H10 120.6 . . ?
C12 C11 C10 120.0(6) . . ?
C12 C11 H11 120.0 . . ?
C10 C11 H11 120.0 . . ?
N2 C12 C11 119.1(6) . . ?
N2 C12 C13 117.6(5) . . ?
C11 C12 C13 123.0(6) . . ?
C12 C13 N4 114.7(5) . . ?
C12 C13 H13A 108.6 . . ?
N4 C13 H13A 108.6 . . ?
C12 C13 H13B 108.6 . . ?
N4 C13 H13B 108.6 . . ?
H13A C13 H13B 107.6 . . ?
C1 C14 N4 112.2(5) . . ?
C1 C14 H14A 109.2 . . ?
N4 C14 H14A 109.2 . . ?
C1 C14 H14B 109.2 . . ?
N4 C14 H14B 109.2 . . ?
H14A C14 H14B 107.9 . . ?
C16 C15 C17 109.5(6) . . ?
C16 C15 C18 108.3(7) . . ?
C17 C15 C18 108.0(6) . . ?
C16 C15 N3 111.1(6) . . ?
C17 C15 N3 111.6(6) . . ?
C18 C15 N3 108.3(6) . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C15 C17 H17A 109.5 . . ?
C15 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C15 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C15 C18 H18A 109.5 . . ?
C15 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C15 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C22 C19 C20 108.0(6) . . ?
C22 C19 N4 108.8(6) . . ?
C20 C19 N4 111.4(6) . . ?
C22 C19 C21 109.3(6) . . ?
C20 C19 C21 107.5(6) . . ?
N4 C19 C21 111.8(6) . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C19 C21 H21A 109.5 . . ?
C19 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C19 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C19 C22 H22A 109.5 . . ?
C19 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C19 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
F1 C23 F2 106.1(6) . . ?
F1 C23 F3 103.7(6) . . ?
F2 C23 F3 103.1(6) . . ?
F1 C23 Ni1 116.1(5) . . ?
F2 C23 Ni1 113.8(5) . . ?
F3 C23 Ni1 112.7(5) . . ?
F4 C24 F5 104.0(6) . . ?
F4 C24 F6 103.9(6) . . ?
F5 C24 F6 104.0(6) . . ?
F4 C24 Ni1 115.0(5) . . ?
F5 C24 Ni1 112.6(5) . . ?
F6 C24 Ni1 116.0(5) . . ?
F7 P1 F11 92.6(3) . . ?
F7 P1 F10 90.2(3) . . ?
F11 P1 F10 91.0(3) . . ?
F7 P1 F8 89.3(3) . . ?
F11 P1 F8 90.6(3) . . ?
F10 P1 F8 178.3(3) . . ?
F7 P1 F9 178.2(3) . . ?
F11 P1 F9 89.1(3) . . ?
F10 P1 F9 89.5(3) . . ?
F8 P1 F9 90.9(3) . . ?
F7 P1 F12 89.7(3) . . ?
F11 P1 F12 177.7(3) . . ?
F10 P1 F12 88.8(3) . . ?
F8 P1 F12 89.6(3) . . ?
F9 P1 F12 88.6(3) . . ?
C1S O1S C4S 99.8(9) . . ?
O1S C1S C2S 109.1(11) . . ?
O1S C1S H1S1 109.9 . . ?
C2S C1S H1S1 109.9 . . ?
O1S C1S H1S2 109.9 . . ?
C2S C1S H1S2 109.9 . . ?
H1S1 C1S H1S2 108.3 . . ?
C1S C2S C3S 98.1(10) . . ?
C1S C2S H2SA 112.1 . . ?
C3S C2S H2SA 112.1 . . ?
C1S C2S H2SB 112.1 . . ?
C3S C2S H2SB 112.1 . . ?
H2SA C2S H2SB 109.8 . . ?
C2S C3S C4S 102.5(8) . . ?
C2S C3S H3SA 111.3 . . ?
C4S C3S H3SA 111.3 . . ?
C2S C3S H3SB 111.3 . . ?
C4S C3S H3SB 111.3 . . ?
H3SA C3S H3SB 109.2 . . ?
O1S C4S C3S 109.7(9) . . ?
O1S C4S H4S1 109.7 . . ?
C3S C4S H4S1 109.7 . . ?
O1S C4S H4S2 109.7 . . ?
C3S C4S H4S2 109.7 . . ?
H4S1 C4S H4S2 108.2 . . ?

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 N1 C1 C2 -4.9(9) . . . . ?
Ni1 N1 C1 C2 171.9(5) . . . . ?
C5 N1 C1 C14 172.7(6) . . . . ?
Ni1 N1 C1 C14 -10.5(7) . . . . ?
N1 C1 C2 C3 -0.6(10) . . . . ?
C14 C1 C2 C3 -178.1(6) . . . . ?
C1 C2 C3 C4 3.9(11) . . . . ?
C2 C3 C4 C5 -1.8(11) . . . . ?
C1 N1 C5 C4 7.1(10) . . . . ?
Ni1 N1 C5 C4 -169.6(5) . . . . ?
C1 N1 C5 C6 -166.6(6) . . . . ?
Ni1 N1 C5 C6 16.7(8) . . . . ?
C3 C4 C5 N1 -3.7(10) . . . . ?
C3 C4 C5 C6 169.7(6) . . . . ?
C7 N3 C6 C5 131.0(6) . . . . ?
C15 N3 C6 C5 -108.0(7) . . . . ?
Ni1 N3 C6 C5 29.7(6) . . . . ?
N1 C5 C6 N3 -34.6(9) . . . . ?
C4 C5 C6 N3 151.7(6) . . . . ?
C6 N3 C7 C8 -62.6(8) . . . . ?
C15 N3 C7 C8 176.2(6) . . . . ?
Ni1 N3 C7 C8 40.0(6) . . . . ?
C12 N2 C8 C9 -6.2(11) . . . . ?
Ni1 N2 C8 C9 168.8(6) . . . . ?
C12 N2 C8 C7 173.4(6) . . . . ?
Ni1 N2 C8 C7 -11.6(9) . . . . ?
N3 C7 C8 N2 -26.5(9) . . . . ?
N3 C7 C8 C9 153.0(7) . . . . ?
N2 C8 C9 C10 -0.5(12) . . . . ?
C7 C8 C9 C10 179.9(7) . . . . ?
C8 C9 C10 C11 4.5(12) . . . . ?
C9 C10 C11 C12 -2.0(12) . . . . ?
C8 N2 C12 C11 8.5(11) . . . . ?
Ni1 N2 C12 C11 -166.5(5) . . . . ?
C8 N2 C12 C13 -165.7(6) . . . . ?
Ni1 N2 C12 C13 19.3(8) . . . . ?
C10 C11 C12 N2 -4.4(11) . . . . ?
C10 C11 C12 C13 169.5(7) . . . . ?
N2 C12 C13 N4 -35.8(9) . . . . ?
C11 C12 C13 N4 150.2(7) . . . . ?
C14 N4 C13 C12 129.9(6) . . . . ?
C19 N4 C13 C12 -110.0(6) . . . . ?
Ni1 N4 C13 C12 29.0(6) . . . . ?
N1 C1 C14 N4 -26.2(8) . . . . ?
C2 C1 C14 N4 151.3(6) . . . . ?
C13 N4 C14 C1 -61.9(7) . . . . ?
C19 N4 C14 C1 178.1(5) . . . . ?
Ni1 N4 C14 C1 39.4(5) . . . . ?
C6 N3 C15 C16 175.4(6) . . . . ?
C7 N3 C15 C16 -64.3(8) . . . . ?
Ni1 N3 C15 C16 53.9(8) . . . . ?
C6 N3 C15 C17 -62.1(8) . . . . ?
C7 N3 C15 C17 58.2(8) . . . . ?
Ni1 N3 C15 C17 176.4(5) . . . . ?
C6 N3 C15 C18 56.6(8) . . . . ?
C7 N3 C15 C18 176.9(6) . . . . ?
Ni1 N3 C15 C18 -64.9(8) . . . . ?
C14 N4 C19 C22 175.4(6) . . . . ?
C13 N4 C19 C22 55.9(7) . . . . ?
Ni1 N4 C19 C22 -64.8(7) . . . . ?
C14 N4 C19 C20 -65.7(7) . . . . ?
C13 N4 C19 C20 174.8(6) . . . . ?
Ni1 N4 C19 C20 54.1(8) . . . . ?
C14 N4 C19 C21 54.5(7) . . . . ?
C13 N4 C19 C21 -64.9(7) . . . . ?
Ni1 N4 C19 C21 174.4(4) . . . . ?
C4S O1S C1S C2S 47.5(15) . . . . ?
O1S C1S C2S C3S -39.2(14) . . . . ?
C1S C2S C3S C4S 14.3(11) . . . . ?
C1S O1S C4S C3S -35.8(14) . . . . ?
C2S C3S C4S O1S 12.2(12) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
# C20 H20B F7  0.98 2.60 3.516(9) 156.5 8_755 
# C20 H20B F10  0.98 2.58 3.421(9) 143.6 8_755 
# C21 H21C F7  0.98 2.62 3.408(9) 137.3 4_566 
C2 H2 F10 0.95 2.51 3.220(8) 131.5 1_655
C4 H4 F6 0.95 2.49 3.332(9) 148.1 3_755
C7 H7A F2 0.99 2.50 3.161(10) 124.3 .
C11 H11 F12 0.95 2.29 3.231(8) 172.7 4_566
C13 H13B O1S 0.99 2.50 3.287(10) 135.9 8_765
C14 H14B F4 0.99 2.51 3.165(8) 123.2 .
C16 H16A F2 0.98 2.38 2.921(9) 114.2 .
C16 H16A F6 0.98 2.31 3.240(9) 159.0 .
C16 H16B F10 0.98 2.51 3.462(8) 163.4 6_656
C16 H16C F5 0.98 2.57 3.414(9) 144.2 6_556
C17 H17A F5 0.98 2.49 3.368(9) 148.2 6_556
C18 H18C F5 0.98 2.31 3.229(9) 155.9 .
C20 H20A F1 0.98 2.35 3.264(10) 154.2 .
C20 H20A F4 0.98 2.36 2.859(9) 111.1 .
C22 H22C F3 0.98 2.35 3.309(9) 164.9 .
C2S H2SA F12 0.99 2.50 3.333(12) 141.9 4_566

_refine_diff_density_max         0.686
_refine_diff_density_min         -0.766
_refine_diff_density_rms         0.095

_shelxl_version_number           2013-3


# start Validation Reply Form
_vrf_RINTA01_l11613              
;
PROBLEM: The value of Rint is greater than 0.25
RESPONSE: Best available crystal was used for data collection.
Due to poor quality crystals the data set is weak and results
in high R~int~.
;
# end Validation Reply Form

