# Supplementary Material (ESI) for New Journal of Chemistry
# This journal is © The Royal Society of Chemistry and 
# The Centre National de la Recherche Scientifique, 2001
# CCDC Number: 440/216

data_shelxl

_publ_contact_author_name          'R. N. Perutz'
_publ_contact_author_address      'Department of Chemistry, University ofYork, YO10 5DD, UK'
_publ_requested_journal           'New Journal of Chemistry'
_publ_section_title               
;
'Coordination and oxidative addition of
octafluornaphthalene at a nickel centre: isolation of an intermediate in
C-F bond activation'
;
_audit_creation_method            SHELXL
_chemical_name_systematic
'nickelbis(triethylphosphine)(eta2--1,2-octafluoronaphthalene)'
_chemical_formula_sum             'C22 H30 F8 Ni P2'
_chemical_formula_weight          567.11

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

_symmetry_cell_setting            triclinic
_symmetry_space_group_name_H-M    'P -1'

loop_
 _symmetry_equiv_pos_as_xyz
 'x, y, z'
 '-x, -y, -z'

_cell_length_a                    11.344(10)
_cell_length_b                    12.614(16)
_cell_length_c                    9.846(13)
_cell_angle_alpha                 112.43(10)
_cell_angle_beta                  96.62(10)
_cell_angle_gamma                 98.50(9)
_cell_volume                      1265.0(25)
_cell_formula_units_Z             2
_cell_measurement_temperature     293(2)
_cell_measurement_reflns_used     20
_cell_measurement_theta_min       6.88
_cell_measurement_theta_max       8.01

_exptl_crystal_description        block
_exptl_crystal_colour             red
_exptl_crystal_size_max           0.4
_exptl_crystal_size_mid           0.3
_exptl_crystal_size_min           0.2
_exptl_crystal_density_meas       'not measured'
_exptl_crystal_density_diffrn     1.489
_exptl_crystal_F_000              584
_exptl_absorpt_coefficient_mu     0.960
_exptl_absorpt_correction_type    'none'
_exptl_absorpt_correction_T_min   0.88
_exptl_absorpt_correction_T_max   1.00

_exptl_special_details
;
 ?
;

_diffrn_ambient_temperature       293(2)
_diffrn_radiation_wavelength      0.71069
_diffrn_radiation_type            MoK\a
_diffrn_radiation_source          'fine-focus sealed tube'
_diffrn_radiation_monochromator   graphite
_diffrn_measurement_device        'Rigaku AFC6'
_diffrn_measurement_method        \w--2\q
_diffrn_standards_number          3
_diffrn_standards_interval_count  150
_diffrn_standards_decay_%         2.1
_diffrn_reflns_number             4457
_diffrn_reflns_av_R_equivalents   0.0000
_diffrn_reflns_av_sigmaI/netI     0.0487
_diffrn_reflns_limit_h_min        0
_diffrn_reflns_limit_h_max        13
_diffrn_reflns_limit_k_min        -15
_diffrn_reflns_limit_k_max        14
_diffrn_reflns_limit_l_min        -11
_diffrn_reflns_limit_l_max        11
_diffrn_reflns_theta_min          2.65
_diffrn_reflns_theta_max          25.03
_reflns_number_total              4457
_reflns_number_gt                 3061
_reflns_threshold_expression      >2sigma(I)

_computing_data_collection        'teXsan'
_computing_cell_refinement        'teXsan'
_computing_data_reduction         'teXsan'
_computing_structure_solution     'SHELXS-86 (Sheldrick, 1990)'
_computing_structure_refinement   'SHELXL-93 (Sheldrick, 1993)'
_computing_molecular_graphics     'teXsan'
_computing_publication_material   'SHELXL-93'

_refine_special_details
;
 Refinement on F^2^ for ALL reflections except for 2 with very negative F^2^
 or flagged by the user for potential systematic errors.  Weighted R-factors
 wR and all goodnesses of fit S are based on F^2^, conventional R-factors R
 are based on F, with F set to zero for negative F^2^. The observed criterion
 of F^2^ > 2sigma(F^2^) is used only for calculating _R_factors(gt) etc.
and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F^2^ 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 w=1/[\s^2^(Fo^2^)+(0.0726P)^2^+0.2373P] where P=(Fo^2^+2Fc^2^)/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_number_reflns          4455
_refine_ls_number_parameters      298
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0857
_refine_ls_R_factor_gt            0.0442
_refine_ls_wR_factor_all          0.1334
_refine_ls_wR_factor_ref          0.1114
_refine_ls_goodness_of_fit_all    1.014
_refine_ls_goodness_of_fit_ref    1.040
_refine_ls_restrained_S_all       1.018
_refine_ls_restrained_S_obs       1.040
_refine_ls_shift/su_max           0.045
_refine_ls_shift/su_mean          0.003

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_thermal_displace_type
 _atom_site_occupancy
 _atom_site_calc_flag
 _atom_site_refinement_flags
 _atom_site_disorder_group
Ni1 Ni 0.24049(4) 0.23443(4) 0.03236(5) 0.0468(2) Uani 1 d . .
P1 P 0.18553(10) 0.38633(10) 0.19226(12) 0.0557(3) Uani 1 d . .
P2 P 0.13955(11) 0.19023(10) -0.19290(12) 0.0575(3) Uani 1 d . .
F5 F 0.7107(3) 0.2038(3) -0.1348(4) 0.0984(10) Uani 1 d . .
F6 F 0.6538(3) 0.0103(3) -0.3861(4) 0.1067(11) Uani 1 d . .
F7 F 0.4417(3) -0.1470(3) -0.4481(3) 0.1034(11) Uani 1 d . .
F8 F 0.2851(3) -0.1075(3) -0.2633(3) 0.0888(9) Uani 1 d . .
F4 F 0.6525(3) 0.3372(3) 0.1096(4) 0.0985(10) Uani 1 d . .
F1 F 0.2462(2) 0.0068(2) 0.0021(3) 0.0738(7) Uani 1 d . .
F3 F 0.5117(3) 0.3667(3) 0.3127(3) 0.0927(10) Uani 1 d . .
F2 F 0.3323(2) 0.1785(3) 0.2742(3) 0.0748(8) Uani 1 d . .
C7 C 0.4695(5) -0.0485(5) -0.3221(5) 0.0766(15) Uani 1 d . .
C6 C 0.5757(5) 0.0309(5) -0.2904(6) 0.0760(15) Uani 1 d . .
C5 C 0.6028(4) 0.1297(5) -0.1621(6) 0.0699(13) Uani 1 d . .
C9 C 0.5239(4) 0.1542(4) -0.0608(5) 0.0611(11) Uani 1 d . .
C10 C 0.4120(4) 0.0751(4) -0.0942(5) 0.0560(10) Uani 1 d . .
C8 C 0.3891(4) -0.0274(4) -0.2251(5) 0.0652(12) Uani 1 d . .
C4 C 0.5506(4) 0.2550(4) 0.0792(6) 0.0656(12) Uani 1 d . .
C3 C 0.4776(4) 0.2727(4) 0.1802(5) 0.0647(12) Uani 1 d . .
C1 C 0.3239(4) 0.1045(4) 0.0061(5) 0.0547(10) Uani 1 d . .
C2 C 0.3604(4) 0.2000(4) 0.1513(4) 0.0565(11) Uani 1 d . .
C11 C 0.1956(6) 0.5208(6) 0.5057(6) 0.114(2) Uani 1 d . .
H11A H 0.2281(6) 0.5284(6) 0.6042(6) 0.171 Uiso 1 calc R .
H11B H 0.1086(6) 0.5057(6) 0.4909(6) 0.171 Uiso 1 calc R .
H11C H 0.2249(6) 0.5921(6) 0.4952(6) 0.171 Uiso 1 calc R .
C12 C 0.2355(5) 0.4196(5) 0.3898(5) 0.0785(15) Uani 1 d . .
H12A H 0.2078(5) 0.3494(5) 0.4057(5) 0.094 Uiso 1 calc R .
H12B H 0.3235(5) 0.4355(5) 0.4099(5) 0.094 Uiso 1 calc R .
C13 C 0.3724(7) 0.5519(7) 0.1840(12) 0.161(4) Uani 1 d . .
H13A H 0.3946(7) 0.6246(7) 0.1738(12) 0.241 Uiso 1 calc R .
H13B H 0.3958(7) 0.4904(7) 0.1054(12) 0.241 Uiso 1 calc R .
H13C H 0.4131(7) 0.5591(7) 0.2791(12) 0.241 Uiso 1 calc R .
C14 C 0.2395(6) 0.5236(5) 0.1743(8) 0.098(2) Uani 1 d . .
H14A H 0.1993(6) 0.5186(5) 0.0789(8) 0.118 Uiso 1 calc R .
H14B H 0.2166(6) 0.5872(5) 0.2526(8) 0.118 Uiso 1 calc R .
C15 C 0.0211(4) 0.3810(5) 0.1783(5) 0.0760(15) Uani 1 d . .
H15A H 0.0082(4) 0.4528(5) 0.2534(5) 0.091 Uiso 1 calc R .
H15B H -0.0122(4) 0.3772(5) 0.0809(5) 0.091 Uiso 1 calc R .
C16 C -0.0468(5) 0.2772(6) 0.1996(7) 0.105(2) Uani 1 d . .
H16A H -0.1316(5) 0.2789(6) 0.1913(7) 0.158 Uiso 1 calc R .
H16B H -0.0156(5) 0.2813(6) 0.2968(7) 0.158 Uiso 1 calc R .
H16C H -0.0360(5) 0.2057(6) 0.1242(7) 0.158 Uiso 1 calc R .
C17 C 0.0379(6) 0.2799(6) -0.2266(6) 0.106(2) Uani 1 d . .
H17A H -0.0224(6) 0.2831(6) -0.1636(6) 0.128 Uiso 1 calc R .
H17B H 0.0847(6) 0.3591(6) -0.1938(6) 0.128 Uiso 1 calc R .
C18 C -0.0286(7) 0.2420(7) -0.3863(6) 0.143(4) Uani 1 d . .
H18A H -0.0791(7) 0.2961(7) -0.3894(6) 0.215 Uiso 1 calc R .
H18B H -0.0781(7) 0.1648(7) -0.4200(6) 0.215 Uiso 1 calc R .
H18C H 0.0294(7) 0.2412(7) -0.4502(6) 0.215 Uiso 1 calc R .
C19 C 0.2363(6) 0.1786(6) -0.3323(6) 0.100(2) Uani 1 d . .
H19A H 0.2809(6) 0.1174(6) -0.3391(6) 0.120 Uiso 1 calc R .
H19B H 0.1854(6) 0.1557(6) -0.4292(6) 0.120 Uiso 1 calc R .
C20 C 0.3245(8) 0.2903(9) -0.2970(10) 0.181(5) Uani 1 d . .
H20A H 0.3725(8) 0.2789(9) -0.3736(10) 0.272 Uiso 1 calc R .
H20B H 0.3766(8) 0.3127(9) -0.2023(10) 0.272 Uiso 1 calc R .
H20C H 0.2810(8) 0.3509(9) -0.2925(10) 0.272 Uiso 1 calc R .
C21 C 0.0476(6) 0.0409(5) -0.2767(6) 0.098(2) Uani 1 d . .
H21A H 0.0099(6) 0.0252(5) -0.3779(6) 0.117 Uiso 1 calc R .
H21B H 0.1016(6) -0.0131(5) -0.2838(6) 0.117 Uiso 1 calc R .
C22 C -0.0460(7) 0.0150(7) -0.2006(8) 0.126(3) Uani 1 d . .
H22A H -0.0881(7) -0.0652(7) -0.2543(8) 0.189 Uiso 1 calc R .
H22B H -0.1023(7) 0.0656(7) -0.1956(8) 0.189 Uiso 1 calc R .
H22C H -0.0103(7) 0.0272(7) -0.1012(8) 0.189 Uiso 1 calc R .

loop_
 _atom_site_aniso_label
 _atom_site_aniso_U_11
 _atom_site_aniso_U_22
 _atom_site_aniso_U_33
 _atom_site_aniso_U_23
 _atom_site_aniso_U_13
 _atom_site_aniso_U_12
Ni1 0.0484(3) 0.0503(3) 0.0452(3) 0.0190(2) 0.0106(2) 0.0204(2)
P1 0.0583(7) 0.0533(6) 0.0528(6) 0.0142(5) 0.0140(5) 0.0210(5)
P2 0.0662(7) 0.0648(7) 0.0461(6) 0.0221(5) 0.0111(5) 0.0277(6)
F5 0.079(2) 0.112(2) 0.129(3) 0.060(2) 0.051(2) 0.038(2)
F6 0.130(3) 0.144(3) 0.096(2) 0.066(2) 0.070(2) 0.089(2)
F7 0.136(3) 0.099(2) 0.068(2) 0.010(2) 0.021(2) 0.067(2)
F8 0.085(2) 0.070(2) 0.089(2) 0.007(2) 0.007(2) 0.027(2)
F4 0.061(2) 0.099(2) 0.108(2) 0.018(2) 0.017(2) 0.003(2)
F1 0.077(2) 0.062(2) 0.091(2) 0.0368(14) 0.0220(14) 0.0194(14)
F3 0.067(2) 0.105(2) 0.066(2) -0.004(2) -0.0028(14) 0.018(2)
F2 0.084(2) 0.099(2) 0.062(2) 0.0449(15) 0.0209(14) 0.042(2)
C7 0.099(4) 0.081(4) 0.060(3) 0.023(3) 0.022(3) 0.060(3)
C6 0.092(4) 0.097(4) 0.073(3) 0.049(3) 0.041(3) 0.062(3)
C5 0.061(3) 0.089(4) 0.080(3) 0.045(3) 0.026(2) 0.037(3)
C9 0.060(3) 0.070(3) 0.067(3) 0.035(2) 0.017(2) 0.034(2)
C10 0.059(3) 0.060(3) 0.056(2) 0.025(2) 0.007(2) 0.030(2)
C8 0.070(3) 0.061(3) 0.067(3) 0.023(2) 0.008(2) 0.035(2)
C4 0.049(3) 0.073(3) 0.078(3) 0.033(3) 0.010(2) 0.017(2)
C3 0.053(3) 0.073(3) 0.059(3) 0.017(2) 0.001(2) 0.023(2)
C1 0.051(2) 0.055(2) 0.063(3) 0.027(2) 0.011(2) 0.020(2)
C2 0.059(3) 0.074(3) 0.046(2) 0.029(2) 0.013(2) 0.029(2)
C11 0.097(4) 0.152(6) 0.057(3) -0.006(3) 0.004(3) 0.060(4)
C12 0.070(3) 0.100(4) 0.050(3) 0.009(3) 0.005(2) 0.033(3)
C13 0.124(7) 0.108(6) 0.262(12) 0.091(7) 0.048(7) 0.007(5)
C14 0.113(5) 0.062(3) 0.122(5) 0.031(3) 0.038(4) 0.029(3)
C15 0.076(3) 0.094(4) 0.055(3) 0.017(3) 0.015(2) 0.046(3)
C16 0.071(4) 0.111(5) 0.109(5) 0.018(4) 0.030(3) 0.008(3)
C17 0.143(5) 0.128(5) 0.057(3) 0.025(3) 0.010(3) 0.096(5)
C18 0.196(8) 0.177(7) 0.063(4) 0.028(4) 0.000(4) 0.136(7)
C19 0.110(5) 0.147(6) 0.071(4) 0.052(4) 0.037(3) 0.071(4)
C20 0.118(6) 0.294(13) 0.143(7) 0.126(9) 0.031(6) -0.030(7)
C21 0.122(5) 0.092(4) 0.059(3) 0.017(3) -0.008(3) 0.020(4)
C22 0.110(5) 0.146(7) 0.106(5) 0.052(5) 0.007(4) -0.010(5)

_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 C2 1.899(4) . ?
Ni1 C1 1.959(4) . ?
Ni1 P1 2.194(3) . ?
Ni1 P2 2.196(3) . ?
P1 C12 1.826(5) . ?
P1 C14 1.831(6) . ?
P1 C15 1.844(5) . ?
P2 C17 1.817(5) . ?
P2 C21 1.831(7) . ?
P2 C19 1.831(6) . ?
F5 C5 1.356(6) . ?
F6 C6 1.348(5) . ?
F7 C7 1.341(6) . ?
F8 C8 1.345(6) . ?
F4 C4 1.353(6) . ?
F1 C1 1.390(5) . ?
F3 C3 1.350(6) . ?
F2 C2 1.397(5) . ?
C7 C6 1.368(8) . ?
C7 C8 1.376(7) . ?
C6 C5 1.356(8) . ?
C5 C9 1.394(6) . ?
C9 C10 1.412(7) . ?
C9 C4 1.435(7) . ?
C10 C8 1.397(6) . ?
C10 C1 1.472(6) . ?
C4 C3 1.341(6) . ?
C3 C2 1.429(6) . ?
C1 C2 1.438(6) . ?
C11 C12 1.521(7) . ?
C13 C14 1.480(9) . ?
C15 C16 1.516(8) . ?
C17 C18 1.522(8) . ?
C19 C20 1.495(10) . ?
C21 C22 1.437(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
C2 Ni1 C1 43.7(2) . . ?
C2 Ni1 P1 104.2(2) . . ?
C1 Ni1 P1 146.19(14) . . ?
C2 Ni1 P2 146.82(14) . . ?
C1 Ni1 P2 103.8(2) . . ?
P1 Ni1 P2 108.99(11) . . ?
C12 P1 C14 104.5(3) . . ?
C12 P1 C15 102.6(2) . . ?
C14 P1 C15 101.8(3) . . ?
C12 P1 Ni1 115.9(2) . . ?
C14 P1 Ni1 113.6(2) . . ?
C15 P1 Ni1 116.6(2) . . ?
C17 P2 C21 104.5(3) . . ?
C17 P2 C19 103.0(3) . . ?
C21 P2 C19 99.4(3) . . ?
C17 P2 Ni1 121.2(2) . . ?
C21 P2 Ni1 112.3(2) . . ?
C19 P2 Ni1 113.7(2) . . ?
F7 C7 C6 120.7(5) . . ?
F7 C7 C8 119.2(6) . . ?
C6 C7 C8 120.0(5) . . ?
F6 C6 C5 120.1(6) . . ?
F6 C6 C7 119.9(5) . . ?
C5 C6 C7 120.0(5) . . ?
F5 C5 C6 117.4(5) . . ?
F5 C5 C9 120.9(5) . . ?
C6 C5 C9 121.7(5) . . ?
C5 C9 C10 119.0(5) . . ?
C5 C9 C4 123.8(5) . . ?
C10 C9 C4 117.2(4) . . ?
C8 C10 C9 117.5(4) . . ?
C8 C10 C1 122.9(4) . . ?
C9 C10 C1 119.5(4) . . ?
F8 C8 C7 117.5(5) . . ?
F8 C8 C10 120.9(4) . . ?
C7 C8 C10 121.6(5) . . ?
C3 C4 F4 118.3(5) . . ?
C3 C4 C5 123.0(5) . . ?
F4 C4 C5 118.7(4) . . ?
C4 C3 F3 119.6(4) . . ?
C4 C3 C2 122.9(4) . . ?
F3 C3 C2 117.4(4) . . ?
F1 C1 C2 114.7(4) . . ?
F1 C1 C10 113.5(4) . . ?
C2 C1 C10 120.1(4) . . ?
F1 C1 Ni1 111.2(3) . . ?
C2 C1 Ni1 65.9(2) . . ?
C10 C1 Ni1 123.4(3) . . ?
F2 C2 C3 113.6(4) . . ?
F2 C2 C1 117.6(4) . . ?
C3 C2 C1 116.1(4) . . ?
F2 C2 Ni1 119.6(3) . . ?
C3 C2 Ni1 112.9(3) . . ?
C1 C2 Ni1 70.4(3) . . ?
C11 C12 P1 118.3(4) . . ?
C13 C14 P1 113.8(5) . . ?
C16 C15 P1 113.1(4) . . ?
C18 C17 P2 117.5(4) . . ?
C20 C19 P2 113.2(5) . . ?
C22 C21 P2 116.8(5) . . ?

_refine_diff_density_max    0.496
_refine_diff_density_min   -0.233
_refine_diff_density_rms    0.066