# Electronic Supplementary Material (ESI) for Physical Chemistry Chemical Physics.
# This journal is © the Owner Societies 2014

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#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
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# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_shelxl

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            'tetrabutylphosphonium hexafluorophosphate'
_chemical_melting_point          ?
_chemical_formula_moiety         
;
(C16 P1 H36 +), (P F6 -)
;
_chemical_formula_sum            'C16 H36 F6 P2'
_chemical_formula_weight         404.39

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'
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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/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                   9.7465(2)
_cell_length_b                   14.0652(4)
_cell_length_c                   15.5029(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.2170(10)
_cell_angle_gamma                90.00
_cell_volume                     2121.89(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    113
_cell_measurement_reflns_used    20895
_cell_measurement_theta_min      3.01
_cell_measurement_theta_max      27.48

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.266
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             864
_exptl_absorpt_coefficient_mu    0.252
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.829
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   'RAPID AUTO 2.40 (Rigaku 2006)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      113
_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  'Rigaku R-AXIS RapidII'
_diffrn_measurement_method       'imaging plate'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            20375
_diffrn_reflns_av_R_equivalents  0.0192
_diffrn_reflns_av_sigmaI/netI    0.0160
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         3.00
_diffrn_reflns_theta_max         27.48
_reflns_number_total             4863
_reflns_number_gt                4372
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Rigaku R-AXIS Rapid-II'
_computing_cell_refinement       'RAPID AUTO 2.40 (Rigaku 2006)'
_computing_data_reduction        'RAPID AUTO 2.40 (Rigaku 2006)'
_computing_structure_solution    'SIR92 (Altmare et al., 1994)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0494P)²+1.4178P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4863
_refine_ls_number_parameters     221
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0435
_refine_ls_R_factor_gt           0.0398
_refine_ls_wR_factor_ref         0.1065
_refine_ls_wR_factor_gt          0.1041
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_restrained_S_all      1.060
_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
P2 P 0.75981(4) 0.37000(3) 0.18173(3) 0.02274(11) Uani 1 1 d . . .
P1 P 0.26963(4) 0.52390(3) 0.19333(2) 0.01975(10) Uani 1 1 d . . .
F1 F 0.66492(10) 0.44935(8) 0.22202(7) 0.0355(2) Uani 1 1 d . . .
F2 F 0.85438(12) 0.29025(8) 0.14169(9) 0.0488(3) Uani 1 1 d . . .
F5 F 0.79452(16) 0.44107(10) 0.10525(9) 0.0618(4) Uani 1 1 d . . .
F6 F 0.63046(12) 0.33320(11) 0.12406(9) 0.0579(4) Uani 1 1 d . . .
F4 F 0.88957(11) 0.41036(10) 0.23686(9) 0.0522(3) Uani 1 1 d . . .
F3 F 0.72568(16) 0.30022(10) 0.25719(9) 0.0617(4) Uani 1 1 d . . .
C32 C 0.47307(15) 0.58651(11) 0.08836(9) 0.0232(3) Uani 1 1 d . . .
H32A H 0.5107 0.5230 0.0839 0.028 Uiso 1 1 calc R . .
H32B H 0.3991 0.5932 0.0442 0.028 Uiso 1 1 calc R . .
C13 C 0.26890(17) 0.22757(11) 0.19029(11) 0.0278(3) Uani 1 1 d . . .
H13A H 0.3027 0.2203 0.1330 0.033 Uiso 1 1 calc R . .
H13B H 0.3455 0.2177 0.2321 0.033 Uiso 1 1 calc R . .
C21 C 0.19890(16) 0.54868(11) 0.29568(10) 0.0251(3) Uani 1 1 d . . .
H21A H 0.1775 0.6159 0.2980 0.030 Uiso 1 1 calc R . .
H21B H 0.1132 0.5141 0.2985 0.030 Uiso 1 1 calc R . .
C42 C 0.10274(16) 0.65361(11) 0.10203(10) 0.0260(3) Uani 1 1 d . . .
H42A H 0.0905 0.6799 0.1589 0.031 Uiso 1 1 calc R . .
H42B H 0.1790 0.6865 0.0777 0.031 Uiso 1 1 calc R . .
C11 C 0.32588(15) 0.40220(11) 0.18838(10) 0.0233(3) Uani 1 1 d . . .
H11A H 0.3647 0.3916 0.1329 0.028 Uiso 1 1 calc R . .
H11B H 0.3986 0.3923 0.2328 0.028 Uiso 1 1 calc R . .
C31 C 0.41516(15) 0.59905(11) 0.17779(9) 0.0214(3) Uani 1 1 d . . .
H31A H 0.3883 0.6649 0.1848 0.026 Uiso 1 1 calc R . .
H31B H 0.4868 0.5848 0.2219 0.026 Uiso 1 1 calc R . .
C23 C 0.2243(2) 0.55185(14) 0.45795(11) 0.0381(4) Uani 1 1 d . . .
H23A H 0.2117 0.6203 0.4581 0.046 Uiso 1 1 calc R . .
H23B H 0.1341 0.5227 0.4583 0.046 Uiso 1 1 calc R . .
C44 C -0.06610(19) 0.77471(15) 0.04069(13) 0.0406(4) Uani 1 1 d . . .
H44A H -0.0804 0.7975 0.0979 0.061 Uiso 1 1 calc R . .
H44B H -0.1490 0.7825 0.0050 0.061 Uiso 1 1 calc R . .
H44C H 0.0067 0.8103 0.0167 0.061 Uiso 1 1 calc R . .
C14 C 0.1596(2) 0.15290(13) 0.20371(12) 0.0360(4) Uani 1 1 d . . .
H14A H 0.1274 0.1589 0.2608 0.054 Uiso 1 1 calc R . .
H14B H 0.1980 0.0907 0.1968 0.054 Uiso 1 1 calc R . .
H14C H 0.0842 0.1619 0.1619 0.054 Uiso 1 1 calc R . .
C43 C -0.02748(16) 0.67027(13) 0.04471(11) 0.0303(3) Uani 1 1 d . . .
H43A H -0.0133 0.6475 -0.0132 0.036 Uiso 1 1 calc R . .
H43B H -0.1025 0.6342 0.0671 0.036 Uiso 1 1 calc R . .
C22 C 0.29133(18) 0.52324(12) 0.37538(10) 0.0297(3) Uani 1 1 d . . .
H22A H 0.3086 0.4553 0.3761 0.036 Uiso 1 1 calc R . .
H22B H 0.3788 0.5556 0.3726 0.036 Uiso 1 1 calc R . .
C41 C 0.13693(15) 0.54731(11) 0.11046(10) 0.0243(3) Uani 1 1 d . . .
H41A H 0.1665 0.5241 0.0556 0.029 Uiso 1 1 calc R . .
H41B H 0.0546 0.5128 0.1237 0.029 Uiso 1 1 calc R . .
C12 C 0.21345(16) 0.32808(11) 0.20007(10) 0.0248(3) Uani 1 1 d . . .
H12A H 0.1779 0.3352 0.2569 0.030 Uiso 1 1 calc R . .
H12B H 0.1384 0.3387 0.1574 0.030 Uiso 1 1 calc R . .
C34 C 0.5318(2) 0.76023(14) 0.06342(13) 0.0411(4) Uani 1 1 d . . .
H34A H 0.4608 0.7632 0.0180 0.049 Uiso 1 1 calc R . .
H34B H 0.6058 0.8017 0.0500 0.049 Uiso 1 1 calc R . .
H34C H 0.4951 0.7798 0.1168 0.049 Uiso 1 1 calc R . .
C24 C 0.3075(3) 0.52304(16) 0.53942(12) 0.0485(5) Uani 1 1 d . . .
H24A H 0.3108 0.4550 0.5433 0.073 Uiso 1 1 calc R . .
H24B H 0.2653 0.5484 0.5889 0.073 Uiso 1 1 calc R . .
H24C H 0.3992 0.5476 0.5375 0.073 Uiso 1 1 calc R . .
C33 C 0.58479(17) 0.65903(13) 0.07216(11) 0.0308(4) Uani 1 1 d . . .
H33A H 0.6541 0.6564 0.1195 0.037 Uiso 1 1 calc R . .
H33B H 0.6286 0.6418 0.0197 0.037 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
P2 F3 1.5767(12) . ?
P2 F6 1.5906(12) . ?
P2 F4 1.5909(11) . ?
P2 F1 1.5987(10) . ?
P2 F2 1.5992(11) . ?
P2 F5 1.6015(12) . ?
P1 C31 1.7960(15) . ?
P1 C21 1.7993(15) . ?
P1 C11 1.8003(15) . ?
P1 C41 1.8014(15) . ?
C32 C33 1.523(2) . ?
C32 C31 1.5361(19) . ?
C32 H32A 0.9700 . ?
C32 H32B 0.9700 . ?
C13 C14 1.519(2) . ?
C13 C12 1.524(2) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C21 C22 1.530(2) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C42 C43 1.526(2) . ?
C42 C41 1.536(2) . ?
C42 H42A 0.9700 . ?
C42 H42B 0.9700 . ?
C11 C12 1.531(2) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C31 H31A 0.9700 . ?
C31 H31B 0.9700 . ?
C23 C24 1.517(3) . ?
C23 C22 1.524(2) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C44 C43 1.517(3) . ?
C44 H44A 0.9600 . ?
C44 H44B 0.9600 . ?
C44 H44C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C43 H43A 0.9700 . ?
C43 H43B 0.9700 . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C41 H41A 0.9700 . ?
C41 H41B 0.9700 . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C34 C33 1.518(3) . ?
C34 H34A 0.9600 . ?
C34 H34B 0.9600 . ?
C34 H34C 0.9600 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C33 H33A 0.9700 . ?
C33 H33B 0.9700 . ?

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
F3 P2 F6 91.19(9) . . ?
F3 P2 F4 91.03(9) . . ?
F6 P2 F4 177.70(9) . . ?
F3 P2 F1 89.65(7) . . ?
F6 P2 F1 89.38(6) . . ?
F4 P2 F1 90.05(6) . . ?
F3 P2 F2 90.09(8) . . ?
F6 P2 F2 90.54(7) . . ?
F4 P2 F2 90.03(7) . . ?
F1 P2 F2 179.73(7) . . ?
F3 P2 F5 179.87(10) . . ?
F6 P2 F5 88.89(9) . . ?
F4 P2 F5 88.88(8) . . ?
F1 P2 F5 90.25(7) . . ?
F2 P2 F5 90.00(7) . . ?
C31 P1 C21 110.42(7) . . ?
C31 P1 C11 108.00(7) . . ?
C21 P1 C11 110.76(7) . . ?
C31 P1 C41 109.73(7) . . ?
C21 P1 C41 107.35(7) . . ?
C11 P1 C41 110.58(7) . . ?
C33 C32 C31 111.98(12) . . ?
C33 C32 H32A 109.2 . . ?
C31 C32 H32A 109.2 . . ?
C33 C32 H32B 109.2 . . ?
C31 C32 H32B 109.2 . . ?
H32A C32 H32B 107.9 . . ?
C14 C13 C12 111.85(13) . . ?
C14 C13 H13A 109.2 . . ?
C12 C13 H13A 109.2 . . ?
C14 C13 H13B 109.2 . . ?
C12 C13 H13B 109.2 . . ?
H13A C13 H13B 107.9 . . ?
C22 C21 P1 115.44(11) . . ?
C22 C21 H21A 108.4 . . ?
P1 C21 H21A 108.4 . . ?
C22 C21 H21B 108.4 . . ?
P1 C21 H21B 108.4 . . ?
H21A C21 H21B 107.5 . . ?
C43 C42 C41 111.62(13) . . ?
C43 C42 H42A 109.3 . . ?
C41 C42 H42A 109.3 . . ?
C43 C42 H42B 109.3 . . ?
C41 C42 H42B 109.3 . . ?
H42A C42 H42B 108.0 . . ?
C12 C11 P1 114.88(10) . . ?
C12 C11 H11A 108.5 . . ?
P1 C11 H11A 108.5 . . ?
C12 C11 H11B 108.5 . . ?
P1 C11 H11B 108.5 . . ?
H11A C11 H11B 107.5 . . ?
C32 C31 P1 112.73(10) . . ?
C32 C31 H31A 109.0 . . ?
P1 C31 H31A 109.0 . . ?
C32 C31 H31B 109.0 . . ?
P1 C31 H31B 109.0 . . ?
H31A C31 H31B 107.8 . . ?
C24 C23 C22 113.23(17) . . ?
C24 C23 H23A 108.9 . . ?
C22 C23 H23A 108.9 . . ?
C24 C23 H23B 108.9 . . ?
C22 C23 H23B 108.9 . . ?
H23A C23 H23B 107.7 . . ?
C43 C44 H44A 109.5 . . ?
C43 C44 H44B 109.5 . . ?
H44A C44 H44B 109.5 . . ?
C43 C44 H44C 109.5 . . ?
H44A C44 H44C 109.5 . . ?
H44B C44 H44C 109.5 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C44 C43 C42 111.65(15) . . ?
C44 C43 H43A 109.3 . . ?
C42 C43 H43A 109.3 . . ?
C44 C43 H43B 109.3 . . ?
C42 C43 H43B 109.3 . . ?
H43A C43 H43B 108.0 . . ?
C23 C22 C21 110.85(14) . . ?
C23 C22 H22A 109.5 . . ?
C21 C22 H22A 109.5 . . ?
C23 C22 H22B 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 108.1 . . ?
C42 C41 P1 112.48(10) . . ?
C42 C41 H41A 109.1 . . ?
P1 C41 H41A 109.1 . . ?
C42 C41 H41B 109.1 . . ?
P1 C41 H41B 109.1 . . ?
H41A C41 H41B 107.8 . . ?
C13 C12 C11 111.08(12) . . ?
C13 C12 H12A 109.4 . . ?
C11 C12 H12A 109.4 . . ?
C13 C12 H12B 109.4 . . ?
C11 C12 H12B 109.4 . . ?
H12A C12 H12B 108.0 . . ?
C33 C34 H34A 109.5 . . ?
C33 C34 H34B 109.5 . . ?
H34A C34 H34B 109.5 . . ?
C33 C34 H34C 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C34 C33 C32 113.56(14) . . ?
C34 C33 H33A 108.9 . . ?
C32 C33 H33A 108.9 . . ?
C34 C33 H33B 108.9 . . ?
C32 C33 H33B 108.9 . . ?
H33A C33 H33B 107.7 . . ?

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
C31 P1 C21 C22 -66.49(14) . . . . ?
C11 P1 C21 C22 53.10(14) . . . . ?
C41 P1 C21 C22 173.92(12) . . . . ?
C31 P1 C11 C12 -179.74(11) . . . . ?
C21 P1 C11 C12 59.23(13) . . . . ?
C41 P1 C11 C12 -59.65(13) . . . . ?
C33 C32 C31 P1 173.01(11) . . . . ?
C21 P1 C31 C32 -175.54(10) . . . . ?
C11 P1 C31 C32 63.22(12) . . . . ?
C41 P1 C31 C32 -57.40(13) . . . . ?
C41 C42 C43 C44 176.57(14) . . . . ?
C24 C23 C22 C21 176.57(16) . . . . ?
P1 C21 C22 C23 177.10(12) . . . . ?
C43 C42 C41 P1 -168.86(11) . . . . ?
C31 P1 C41 C42 -51.27(13) . . . . ?
C21 P1 C41 C42 68.76(13) . . . . ?
C11 P1 C41 C42 -170.31(11) . . . . ?
C14 C13 C12 C11 178.71(14) . . . . ?
P1 C11 C12 C13 177.07(11) . . . . ?
C31 C32 C33 C34 -68.09(18) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.679
_refine_diff_density_min         -0.385
_refine_diff_density_rms         0.053
_database_code_depnum_ccdc_archive 'CCDC 1010901'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_shelxl

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            'tetrabutylphosphonium hexafluorophosphate'
_chemical_melting_point          ?
_chemical_formula_moiety         
;
(C16 P1 H36 +), (P F6 -)
;
_chemical_formula_sum            'C16 H36 F6 P2'
_chemical_formula_weight         404.39

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'
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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/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                   9.8567(12)
_cell_length_b                   14.1385(17)
_cell_length_c                   15.777(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.422(3)
_cell_angle_gamma                90.00
_cell_volume                     2196.6(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    243
_cell_measurement_reflns_used    20860
_cell_measurement_theta_min      1.66
_cell_measurement_theta_max      27.48

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.223
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             864
_exptl_absorpt_coefficient_mu    0.243
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.875
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   'RAPID AUTO 2.40 (Rigaku 2006)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      243
_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  'Rigaku R-AXIS RapidII'
_diffrn_measurement_method       'imaging plate'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            20860
_diffrn_reflns_av_R_equivalents  0.0523
_diffrn_reflns_av_sigmaI/netI    0.0465
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         3.16
_diffrn_reflns_theta_max         27.48
_reflns_number_total             5030
_reflns_number_gt                3382
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Rigaku R-AXIS Rapid-II'
_computing_cell_refinement       'RAPID AUTO 2.40 (Rigaku 2006)'
_computing_data_reduction        'RAPID AUTO 2.40 (Rigaku 2006)'
_computing_structure_solution    'SIR92 (Altmare et al., 1994)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.1125P)²+0.2525P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5030
_refine_ls_number_parameters     298
_refine_ls_number_restraints     255
_refine_ls_R_factor_all          0.0849
_refine_ls_R_factor_gt           0.0624
_refine_ls_wR_factor_ref         0.2073
_refine_ls_wR_factor_gt          0.1840
_refine_ls_goodness_of_fit_ref   1.098
_refine_ls_restrained_S_all      1.167
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
P1 P 0.26661(6) -0.47766(5) 1.19111(4) 0.0540(2) Uani 1 1 d . . .
P2 P 0.76027(6) -0.63136(5) 1.18517(5) 0.0588(3) Uani 1 1 d DU . .
C31 C 0.1972(3) -0.4547(2) 1.29284(18) 0.0671(7) Uani 1 1 d . . .
H31A H 0.1723 -0.3884 1.2951 0.080 Uiso 1 1 calc R . .
H31B H 0.1144 -0.4913 1.2968 0.080 Uiso 1 1 calc R . .
C13 C 0.2739(4) -0.7721(2) 1.1835(2) 0.0802(9) Uani 1 1 d . . .
H13A H 0.3075 -0.7787 1.1269 0.096 Uiso 1 1 calc R . .
H13B H 0.3494 -0.7817 1.2241 0.096 Uiso 1 1 calc R . .
C42 C 0.4695(3) -0.4121(2) 1.08906(17) 0.0634(6) Uani 1 1 d . . .
H42A H 0.5060 -0.4753 1.0833 0.076 Uiso 1 1 calc R . .
H42B H 0.3975 -0.4041 1.0459 0.076 Uiso 1 1 calc R . .
C009 C 0.1359(3) -0.4526(2) 1.11096(19) 0.0651(7) Uani 1 1 d . . .
H00A H 0.1665 -0.4730 1.0563 0.078 Uiso 1 1 calc R . .
H00B H 0.0553 -0.4887 1.1230 0.078 Uiso 1 1 calc R . .
C010 C 0.4096(2) -0.40256(19) 1.17655(16) 0.0566(6) Uani 1 1 d . . .
H01A H 0.3824 -0.3374 1.1847 0.068 Uiso 1 1 calc R . .
H01B H 0.4796 -0.4173 1.2196 0.068 Uiso 1 1 calc R . .
C012 C 0.0991(3) -0.3476(2) 1.1061(2) 0.0712(7) Uani 1 1 d . . .
H01C H 0.0835 -0.3245 1.1628 0.085 Uiso 1 1 calc R . .
H01D H 0.1750 -0.3126 1.0845 0.085 Uiso 1 1 calc R . .
C11 C 0.3244(3) -0.59850(19) 1.18352(19) 0.0655(7) Uani 1 1 d . . .
H11A H 0.3631 -0.6073 1.1285 0.079 Uiso 1 1 calc R . .
H11B H 0.3964 -0.6087 1.2264 0.079 Uiso 1 1 calc R . .
C014 C -0.0247(3) -0.3294(3) 1.0503(2) 0.0812(9) Uani 1 1 d . . .
H01E H -0.1001 -0.3656 1.0709 0.097 Uiso 1 1 calc R . .
H01F H -0.0083 -0.3506 0.9932 0.097 Uiso 1 1 calc R . .
C12 C 0.2158(3) -0.6726(2) 1.1943(2) 0.0710(7) Uani 1 1 d . . .
H12A H 0.1421 -0.6624 1.1526 0.085 Uiso 1 1 calc R . .
H12B H 0.1795 -0.6668 1.2503 0.085 Uiso 1 1 calc R . .
C016 C 0.5805(3) -0.3411(3) 1.0738(2) 0.0788(9) Uani 1 1 d . . .
H01G H 0.6481 -0.3449 1.1202 0.095 Uiso 1 1 calc R . .
H01H H 0.6245 -0.3580 1.0221 0.095 Uiso 1 1 calc R . .
C019 C -0.0616(4) -0.2263(3) 1.0484(3) 0.1037(13) Uani 1 1 d . . .
H01I H -0.0780 -0.2051 1.1048 0.124 Uiso 1 1 calc R . .
H01J H -0.1421 -0.2173 1.0128 0.124 Uiso 1 1 calc R . .
H01K H 0.0117 -0.1905 1.0262 0.124 Uiso 1 1 calc R . .
C020 C 0.2878(4) -0.4767(2) 1.36900(19) 0.0829(9) Uani 1 1 d . . .
H02A H 0.3720 -0.4416 1.3656 0.099 Uiso 1 1 calc R . .
H02B H 0.3096 -0.5436 1.3695 0.099 Uiso 1 1 calc R . .
C021 C 0.1674(4) -0.8447(3) 1.1969(3) 0.0999(11) Uani 1 1 d . . .
H02C H 0.1396 -0.8416 1.2545 0.120 Uiso 1 1 calc R . .
H02D H 0.2034 -0.9064 1.1861 0.120 Uiso 1 1 calc R . .
H02E H 0.0906 -0.8329 1.1589 0.120 Uiso 1 1 calc R . .
C022 C 0.5316(5) -0.2416(3) 1.0664(3) 0.1099(13) Uani 1 1 d . . .
H02F H 0.4678 -0.2363 1.0190 0.132 Uiso 1 1 calc R . .
H02G H 0.6073 -0.2003 1.0581 0.132 Uiso 1 1 calc R . .
H02H H 0.4883 -0.2239 1.1175 0.132 Uiso 1 1 calc R . .
C023 C 0.2198(5) -0.4508(3) 1.4511(2) 0.1123(14) Uani 1 1 d . . .
H02I H 0.2036 -0.3832 1.4514 0.135 Uiso 1 1 calc R . .
H02J H 0.1322 -0.4821 1.4515 0.135 Uiso 1 1 calc R . .
C024 C 0.2975(7) -0.4762(4) 1.5289(3) 0.142(2) Uani 1 1 d . . .
H02K H 0.3085 -0.5436 1.5316 0.170 Uiso 1 1 calc R . .
H02L H 0.2499 -0.4550 1.5772 0.170 Uiso 1 1 calc R . .
H02M H 0.3852 -0.4466 1.5290 0.170 Uiso 1 1 calc R . .
F3 F 0.6644(2) -0.5549(2) 1.2239(2) 0.0975(8) Uani 0.88 1 d PDU A 1
F5 F 0.8565(3) -0.7083(2) 1.1483(3) 0.1300(12) Uani 0.88 1 d PDU B 1
F22 F 0.8123(7) -0.5585(4) 1.1193(4) 0.172(3) Uani 0.75 1 d PDU B 2
F24 F 0.7091(7) -0.7024(4) 1.2488(4) 0.171(3) Uani 0.75 1 d PDU B 2
F21 F 0.6409(5) -0.6573(5) 1.1209(3) 0.1130(16) Uani 0.66 1 d PDU B 3
F23 F 0.8796(5) -0.5986(5) 1.2471(4) 0.124(2) Uani 0.66 1 d PDU B 3
F101 F 0.738(2) -0.5887(11) 1.0973(5) 0.189(9) Uani 0.27 1 d PDU B 4
F104 F 0.6350(9) -0.6993(9) 1.1661(11) 0.127(5) Uani 0.27 1 d PDU C 4
F103 F 0.7748(16) -0.6788(11) 1.2738(6) 0.152(6) Uani 0.27 1 d PDU B 4
F102 F 0.8836(10) -0.5693(8) 1.2108(10) 0.104(4) Uani 0.27 1 d PDU B 4
F202 F 0.8619(18) -0.639(3) 1.1127(10) 0.150(13) Uani 0.08 1 d PDU B 5
F204 F 0.6604(16) -0.627(3) 1.2590(9) 0.120(9) Uani 0.08 1 d PDU B 5
F201 F 0.723(3) -0.5257(7) 1.167(2) 0.192(15) Uani 0.08 1 d PDU B 5
F203 F 0.795(3) -0.7366(7) 1.204(2) 0.169(14) Uani 0.08 1 d PDU B 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
P1 C010 1.787(3) . ?
P1 C31 1.801(3) . ?
P1 C009 1.802(3) . ?
P1 C11 1.807(3) . ?
P2 F101 1.519(6) . ?
P2 F24 1.520(4) . ?
P2 F102 1.539(6) . ?
P2 F103 1.552(7) . ?
P2 F203 1.552(8) . ?
P2 F202 1.555(8) . ?
P2 F204 1.558(8) . ?
P2 F201 1.560(8) . ?
P2 F21 1.564(3) . ?
P2 F22 1.565(4) . ?
P2 F23 1.567(4) . ?
P2 F5 1.571(2) . ?
C31 C020 1.499(4) . ?
C31 H31A 0.9700 . ?
C31 H31B 0.9700 . ?
C13 C021 1.489(5) . ?
C13 C12 1.531(4) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C42 C016 1.511(4) . ?
C42 C010 1.530(3) . ?
C42 H42A 0.9700 . ?
C42 H42B 0.9700 . ?
C009 C012 1.529(4) . ?
C009 H00A 0.9700 . ?
C009 H00B 0.9700 . ?
C010 H01A 0.9700 . ?
C010 H01B 0.9700 . ?
C012 C014 1.496(4) . ?
C012 H01C 0.9700 . ?
C012 H01D 0.9700 . ?
C11 C12 1.513(4) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C014 C019 1.503(5) . ?
C014 H01E 0.9700 . ?
C014 H01F 0.9700 . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C016 C022 1.490(5) . ?
C016 H01G 0.9700 . ?
C016 H01H 0.9700 . ?
C019 H01I 0.9600 . ?
C019 H01J 0.9600 . ?
C019 H01K 0.9600 . ?
C020 C023 1.528(5) . ?
C020 H02A 0.9700 . ?
C020 H02B 0.9700 . ?
C021 H02C 0.9600 . ?
C021 H02D 0.9600 . ?
C021 H02E 0.9600 . ?
C022 H02F 0.9600 . ?
C022 H02G 0.9600 . ?
C022 H02H 0.9600 . ?
C023 C024 1.464(6) . ?
C023 H02I 0.9700 . ?
C023 H02J 0.9700 . ?
C024 H02K 0.9600 . ?
C024 H02L 0.9600 . ?
C024 H02M 0.9600 . ?

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
C010 P1 C31 109.83(13) . . ?
C010 P1 C009 109.71(13) . . ?
C31 P1 C009 107.62(14) . . ?
C010 P1 C11 107.49(12) . . ?
C31 P1 C11 111.22(14) . . ?
C009 P1 C11 110.97(14) . . ?
F101 P2 F24 145.6(8) . . ?
F101 P2 F102 95.4(9) . . ?
F24 P2 F102 118.9(6) . . ?
F101 P2 F103 176.4(9) . . ?
F24 P2 F103 30.7(6) . . ?
F102 P2 F103 88.2(5) . . ?
F101 P2 F203 125.2(14) . . ?
F24 P2 F203 46.9(15) . . ?
F102 P2 F203 109.5(11) . . ?
F103 P2 F203 53.3(14) . . ?
F101 P2 F202 55.2(12) . . ?
F24 P2 F202 133.0(14) . . ?
F102 P2 F202 72.9(10) . . ?
F103 P2 F202 126.5(13) . . ?
F203 P2 F202 86.1(10) . . ?
F101 P2 F204 126.4(13) . . ?
F24 P2 F204 45.4(14) . . ?
F102 P2 F204 107.2(11) . . ?
F103 P2 F204 51.9(13) . . ?
F203 P2 F204 92(2) . . ?
F202 P2 F204 178(2) . . ?
F101 P2 F201 55.4(12) . . ?
F24 P2 F201 132.1(14) . . ?
F102 P2 F201 71.2(10) . . ?
F103 P2 F201 126.1(13) . . ?
F203 P2 F201 179(2) . . ?
F202 P2 F201 95(2) . . ?
F204 P2 F201 86.7(11) . . ?
F101 P2 F21 55.0(7) . . ?
F24 P2 F21 90.7(3) . . ?
F102 P2 F21 150.2(6) . . ?
F103 P2 F21 121.4(6) . . ?
F203 P2 F21 92.9(8) . . ?
F202 P2 F21 89.8(8) . . ?
F204 P2 F21 90.8(7) . . ?
F201 P2 F21 86.8(8) . . ?
F101 P2 F22 34.0(7) . . ?
F24 P2 F22 179.6(4) . . ?
F102 P2 F22 61.4(6) . . ?
F103 P2 F22 149.6(6) . . ?
F203 P2 F22 133.1(15) . . ?
F202 P2 F22 47.0(14) . . ?
F204 P2 F22 134.6(15) . . ?
F201 P2 F22 48.0(14) . . ?
F21 P2 F22 89.0(3) . . ?
F101 P2 F23 121.8(8) . . ?
F24 P2 F23 92.5(4) . . ?
F102 P2 F23 26.4(6) . . ?
F103 P2 F23 61.8(6) . . ?
F203 P2 F23 90.7(8) . . ?
F202 P2 F23 89.4(8) . . ?
F204 P2 F23 90.1(7) . . ?
F201 P2 F23 89.6(8) . . ?
F21 P2 F23 176.2(3) . . ?
F22 P2 F23 87.8(3) . . ?
F101 P2 F5 90.2(5) . . ?
F24 P2 F5 90.5(3) . . ?
F102 P2 F5 90.6(5) . . ?
F103 P2 F5 90.0(6) . . ?
F203 P2 F5 43.6(14) . . ?
F202 P2 F5 42.5(13) . . ?
F204 P2 F5 135.9(15) . . ?
F201 P2 F5 137.4(14) . . ?
F21 P2 F5 92.7(2) . . ?
F22 P2 F5 89.4(3) . . ?
F23 P2 F5 89.3(3) . . ?
C020 C31 P1 116.2(2) . . ?
C020 C31 H31A 108.2 . . ?
P1 C31 H31A 108.2 . . ?
C020 C31 H31B 108.2 . . ?
P1 C31 H31B 108.2 . . ?
H31A C31 H31B 107.4 . . ?
C021 C13 C12 110.4(3) . . ?
C021 C13 H13A 109.6 . . ?
C12 C13 H13A 109.6 . . ?
C021 C13 H13B 109.6 . . ?
C12 C13 H13B 109.6 . . ?
H13A C13 H13B 108.1 . . ?
C016 C42 C010 113.2(2) . . ?
C016 C42 H42A 108.9 . . ?
C010 C42 H42A 108.9 . . ?
C016 C42 H42B 108.9 . . ?
C010 C42 H42B 108.9 . . ?
H42A C42 H42B 107.7 . . ?
C012 C009 P1 112.80(19) . . ?
C012 C009 H00A 109.0 . . ?
P1 C009 H00A 109.0 . . ?
C012 C009 H00B 109.0 . . ?
P1 C009 H00B 109.0 . . ?
H00A C009 H00B 107.8 . . ?
C42 C010 P1 113.60(18) . . ?
C42 C010 H01A 108.8 . . ?
P1 C010 H01A 108.8 . . ?
C42 C010 H01B 108.8 . . ?
P1 C010 H01B 108.8 . . ?
H01A C010 H01B 107.7 . . ?
C014 C012 C009 112.5(3) . . ?
C014 C012 H01C 109.1 . . ?
C009 C012 H01C 109.1 . . ?
C014 C012 H01D 109.1 . . ?
C009 C012 H01D 109.1 . . ?
H01C C012 H01D 107.8 . . ?
C12 C11 P1 114.88(19) . . ?
C12 C11 H11A 108.5 . . ?
P1 C11 H11A 108.5 . . ?
C12 C11 H11B 108.5 . . ?
P1 C11 H11B 108.5 . . ?
H11A C11 H11B 107.5 . . ?
C012 C014 C019 111.7(3) . . ?
C012 C014 H01E 109.3 . . ?
C019 C014 H01E 109.3 . . ?
C012 C014 H01F 109.3 . . ?
C019 C014 H01F 109.3 . . ?
H01E C014 H01F 107.9 . . ?
C11 C12 C13 110.7(3) . . ?
C11 C12 H12A 109.5 . . ?
C13 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C13 C12 H12B 109.5 . . ?
H12A C12 H12B 108.1 . . ?
C022 C016 C42 113.9(3) . . ?
C022 C016 H01G 108.8 . . ?
C42 C016 H01G 108.8 . . ?
C022 C016 H01H 108.8 . . ?
C42 C016 H01H 108.8 . . ?
H01G C016 H01H 107.7 . . ?
C014 C019 H01I 109.5 . . ?
C014 C019 H01J 109.5 . . ?
H01I C019 H01J 109.5 . . ?
C014 C019 H01K 109.5 . . ?
H01I C019 H01K 109.5 . . ?
H01J C019 H01K 109.5 . . ?
C31 C020 C023 111.3(3) . . ?
C31 C020 H02A 109.4 . . ?
C023 C020 H02A 109.4 . . ?
C31 C020 H02B 109.4 . . ?
C023 C020 H02B 109.4 . . ?
H02A C020 H02B 108.0 . . ?
C13 C021 H02C 109.5 . . ?
C13 C021 H02D 109.5 . . ?
H02C C021 H02D 109.5 . . ?
C13 C021 H02E 109.5 . . ?
H02C C021 H02E 109.5 . . ?
H02D C021 H02E 109.5 . . ?
C016 C022 H02F 109.5 . . ?
C016 C022 H02G 109.5 . . ?
H02F C022 H02G 109.5 . . ?
C016 C022 H02H 109.5 . . ?
H02F C022 H02H 109.5 . . ?
H02G C022 H02H 109.5 . . ?
C024 C023 C020 114.8(4) . . ?
C024 C023 H02I 108.6 . . ?
C020 C023 H02I 108.6 . . ?
C024 C023 H02J 108.6 . . ?
C020 C023 H02J 108.6 . . ?
H02I C023 H02J 107.5 . . ?
C023 C024 H02K 109.5 . . ?
C023 C024 H02L 109.5 . . ?
H02K C024 H02L 109.5 . . ?
C023 C024 H02M 109.5 . . ?
H02K C024 H02M 109.5 . . ?
H02L C024 H02M 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
C010 P1 C31 C020 -64.0(3) . . . . ?
C009 P1 C31 C020 176.6(2) . . . . ?
C11 P1 C31 C020 54.9(3) . . . . ?
C010 P1 C009 C012 -52.6(2) . . . . ?
C31 P1 C009 C012 66.8(2) . . . . ?
C11 P1 C009 C012 -171.3(2) . . . . ?
C016 C42 C010 P1 173.8(2) . . . . ?
C31 P1 C010 C42 -175.95(19) . . . . ?
C009 P1 C010 C42 -57.9(2) . . . . ?
C11 P1 C010 C42 62.9(2) . . . . ?
P1 C009 C012 C014 -170.3(2) . . . . ?
C010 P1 C11 C12 -180.0(2) . . . . ?
C31 P1 C11 C12 59.8(3) . . . . ?
C009 P1 C11 C12 -60.0(3) . . . . ?
C009 C012 C014 C019 178.3(3) . . . . ?
P1 C11 C12 C13 177.9(2) . . . . ?
C021 C13 C12 C11 178.2(3) . . . . ?
C010 C42 C016 C022 -68.5(4) . . . . ?
P1 C31 C020 C023 177.8(3) . . . . ?
C31 C020 C023 C024 175.9(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.575
_refine_diff_density_min         -0.377
_refine_diff_density_rms         0.056
_database_code_depnum_ccdc_archive 'CCDC 1010902'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_shelxl

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            'tetrabutylphosphonium hexafluorophosphate'
_chemical_melting_point          ?
_chemical_formula_moiety         
;
(C16 P1 H36 +), (P F6 -)
;
_chemical_formula_sum            'C16 H36 F6 P2'
_chemical_formula_weight         404.39

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'
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'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   Pmcn

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

_cell_length_a                   9.9807(9)
_cell_length_b                   13.8901(15)
_cell_length_c                   16.2367(16)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2250.9(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    273
_cell_measurement_reflns_used    21352
_cell_measurement_theta_min      3.69
_cell_measurement_theta_max      27.50

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.193
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             864
_exptl_absorpt_coefficient_mu    0.237
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.626
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   'RAPID AUTO 2.40 (Rigaku 2006)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      273
_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  'Rigaku R-AXIS RapidII'
_diffrn_measurement_method       'imaging plate'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            21352
_diffrn_reflns_av_R_equivalents  0.0249
_diffrn_reflns_av_sigmaI/netI    0.0141
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         3.19
_diffrn_reflns_theta_max         27.48
_reflns_number_total             2715
_reflns_number_gt                1234
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Rigaku R-AXIS Rapid-II'
_computing_cell_refinement       'RAPID AUTO 2.40 (Rigaku 2006)'
_computing_data_reduction        'RAPID AUTO 2.40 (Rigaku 2006)'
_computing_structure_solution    'SIR92 (Altmare et al., 1994)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.2000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2715
_refine_ls_number_parameters     197
_refine_ls_number_restraints     107
_refine_ls_R_factor_all          0.1426
_refine_ls_R_factor_gt           0.0951
_refine_ls_wR_factor_ref         0.3493
_refine_ls_wR_factor_gt          0.3034
_refine_ls_goodness_of_fit_ref   1.137
_refine_ls_restrained_S_all      1.364
_refine_ls_shift/su_max          0.044
_refine_ls_shift/su_mean         0.001

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
C31 C 0.1789(10) 0.9587(8) 0.7837(6) 0.128(3) Uani 0.50 1 d PD . .
H31B H 0.0968 0.9960 0.7862 0.154 Uiso 0.50 1 calc PR A 1
H31A H 0.1530 0.8914 0.7855 0.154 Uiso 0.50 1 calc PR A 1
C21 C 0.1887(10) 1.0958(7) 0.6723(7) 0.129(3) Uani 0.50 1 d PD . .
H21A H 0.1674 1.1002 0.6141 0.154 Uiso 0.50 1 calc PR B 1
H21B H 0.1036 1.0974 0.7011 0.154 Uiso 0.50 1 calc PR B 1
C34A C 0.2500 0.9778(13) 1.0179(7) 0.312(10) Uani 0.50 2 d SPD C 1
H34A H 0.2500 0.9249 1.0560 0.467 Uiso 1 2 calc SR C 1
H34B H 0.1715 1.0164 1.0265 0.467 Uiso 0.50 1 calc PR C 1
H34C H 0.3285 1.0164 1.0265 0.467 Uiso 0.50 1 calc PR C 1
C34B C 0.2500 0.9778(13) 1.0179(7) 0.312(10) Uani 0.50 2 d SP D 2
C13A C -0.0465(8) 0.8321(7) 0.5638(5) 0.189(3) Uani 0.50 1 d P E 1
H13A H -0.1228 0.8599 0.5922 0.227 Uiso 0.50 1 calc PR E 1
H13B H -0.0420 0.8567 0.5079 0.227 Uiso 0.50 1 calc PR E 1
C13B C -0.0465(8) 0.8321(7) 0.5638(5) 0.189(3) Uani 0.50 1 d P F 2
H13C H -0.0663 0.8458 0.5065 0.227 Uiso 0.50 1 calc PR F 2
H13D H -0.1275 0.8490 0.5935 0.227 Uiso 0.50 1 calc PR F 2
C12B C 0.0422(12) 0.9059(11) 0.5853(7) 0.126(3) Uani 0.50 1 d P F 2
H12C H -0.0055 0.9665 0.5808 0.151 Uiso 0.50 1 calc PR F 2
H12D H 0.1135 0.9070 0.5447 0.151 Uiso 0.50 1 calc PR F 2
C11B C 0.1069(10) 0.9018(8) 0.6709(6) 0.103(2) Uani 0.50 1 d P F 2
H11C H 0.1343 0.8359 0.6815 0.123 Uiso 0.50 1 calc PR F 2
H11D H 0.0393 0.9183 0.7115 0.123 Uiso 0.50 1 calc PR F 2
C14A C -0.0467(10) 0.7282(7) 0.5665(5) 0.221(4) Uani 0.50 1 d P E 1
H14A H 0.0394 0.7045 0.5497 0.332 Uiso 1 1 calc R E 1
H14C H -0.1144 0.7039 0.5300 0.332 Uiso 1 1 calc R E 1
H14B H -0.0653 0.7072 0.6216 0.332 Uiso 1 1 calc R E 1
C14B C -0.0467(10) 0.7282(7) 0.5665(5) 0.221(4) Uani 0.50 1 d P F 2
C11A C 0.1236(11) 0.9516(8) 0.6111(8) 0.122(3) Uani 0.50 1 d P E 1
H11A H 0.0438 0.9892 0.6223 0.146 Uiso 0.50 1 calc PR E 1
H11B H 0.1559 0.9690 0.5567 0.146 Uiso 0.50 1 calc PR E 1
C12A C 0.0896(13) 0.8472(10) 0.6126(10) 0.146(5) Uani 0.50 1 d P E 1
H12B H 0.0795 0.8255 0.6690 0.175 Uiso 0.50 1 calc PR E 1
H12A H 0.1607 0.8102 0.5870 0.175 Uiso 0.50 1 calc PR E 1
C23A C 0.2500 1.2771(8) 0.6719(7) 0.205(5) Uani 0.50 2 d SPD G 1
H23A H 0.2275 1.2769 0.6138 0.245 Uiso 0.50 1 calc PR G 1
H23B H 0.1699 1.3002 0.6994 0.245 Uiso 0.50 1 calc PR G 1
C23B C 0.2500 1.2771(8) 0.6719(7) 0.205(5) Uani 0.50 2 d SP . 2
C22A C 0.2500 1.1804(7) 0.6912(6) 0.228(8) Uani 0.50 2 d SPD G 1
H22A H 0.3435 1.1639 0.6830 0.274 Uiso 0.50 1 calc PR G 1
H22B H 0.2391 1.1823 0.7505 0.274 Uiso 0.50 1 calc PR G 1
C22B C 0.2500 1.1804(7) 0.6912(6) 0.228(8) Uani 0.50 2 d SP . 2
C32A C 0.2500 0.9778(7) 0.8565(5) 0.183(4) Uani 0.50 2 d SPD C 1
H32A H 0.3428 0.9711 0.8398 0.219 Uiso 0.50 1 calc PR C 1
H32B H 0.2368 1.0464 0.8644 0.219 Uiso 0.50 1 calc PR C 1
C32B C 0.2500 0.9778(7) 0.8565(5) 0.183(4) Uani 0.50 2 d SP . 2
C33A C 0.2500 0.9420(10) 0.9367(7) 0.346(14) Uani 0.50 2 d SPD C 1
H33A H 0.3271 0.8995 0.9366 0.416 Uiso 0.50 1 calc PR C 1
H33B H 0.1729 0.8995 0.9366 0.416 Uiso 0.50 1 calc PR C 1
C33B C 0.2500 0.9420(10) 0.9367(7) 0.346(14) Uani 0.50 2 d SP D 2
F1 F 0.3595(6) 0.5693(8) 0.7682(7) 0.191(4) Uani 0.720(2) 1 d PDU . .
F2 F 0.3621(6) 0.6766(11) 0.8627(8) 0.236(5) Uani 0.675(2) 1 d PDU . .
F3 F 0.2500 0.6975(14) 0.7403(12) 0.188(8) Uani 0.3954(18) 2 d SPDU . .
C24 C 0.3344(17) 1.3534(11) 0.6782(11) 0.214(8) Uani 0.50 1 d PD . .
H24A H 0.4252 1.3308 0.6804 0.321 Uiso 0.50 1 calc PR G 1
H24C H 0.3144 1.3888 0.7274 0.321 Uiso 0.50 1 calc PR G 1
H24B H 0.3233 1.3945 0.6312 0.321 Uiso 0.50 1 calc PR G 1
P1 P 0.2500 0.62681(13) 0.81349(10) 0.1029(8) Uani 1 2 d SD . .
P2 P 0.2500 0.97921(12) 0.68657(10) 0.1016(8) Uani 1 2 d S . .
F4 F 0.2500 0.5430(17) 0.8757(16) 0.262(16) Uani 0.3954(18) 2 d SPDU . .
F6 F 0.3370(16) 0.5375(9) 0.8137(19) 0.220(10) Uani 0.280(2) 1 d PDU . .
F8 F 0.3376(13) 0.7168(6) 0.8049(17) 0.207(8) Uani 0.325(2) 1 d PDU . .
F5 F 0.3178(15) 0.593(2) 0.8926(7) 0.230(9) Uani 0.325(2) 1 d PDU . .
F7 F 0.3286(14) 0.636(2) 0.7333(5) 0.203(7) Uani 0.280(2) 1 d PDU . .


_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
C31 C32A 1.404(10) . ?
C31 P2 1.753(10) . ?
C31 H31B 0.9700 . ?
C31 H31A 0.9700 . ?
C21 C22A 1.360(9) . ?
C21 P2 1.746(10) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C34A C33A 1.408(10) . ?
C34A H34A 0.9600 . ?
C34A H34B 0.9600 . ?
C34A H34C 0.9600 . ?
C13A C14A 1.444(10) . ?
C13A C12A 1.587(14) . ?
C13A H13A 0.9700 . ?
C13A H13B 0.9700 . ?
C12B C11B 1.534(15) . ?
C12B H12C 0.9700 . ?
C12B H12D 0.9700 . ?
C11B P2 1.806(10) . ?
C11B H11C 0.9700 . ?
C11B H11D 0.9700 . ?
C14A H14A 0.9600 . ?
C14A H14C 0.9600 . ?
C14A H14B 0.9600 . ?
C11A C12A 1.489(17) . ?
C11A P2 1.800(13) . ?
C11A H11A 0.9700 . ?
C11A H11B 0.9700 . ?
C12A H12B 0.9700 . ?
C12A H12A 0.9700 . ?
C23A C24 1.358(10) . ?
C23A C22A 1.379(10) . ?
C23A H23A 0.9700 . ?
C23A H23B 0.9700 . ?
C22A H22A 0.9700 . ?
C22A H22B 0.9700 . ?
C32A C33A 1.394(11) . ?
C32A H32A 0.9700 . ?
C32A H32B 0.9700 . ?
C33A H33A 0.9700 . ?
C33A H33B 0.9700 . ?
F1 P1 1.541(5) . ?
F2 P1 1.539(5) . ?
F3 P1 1.541(8) . ?
C24 H24A 0.9600 . ?
C24 H24C 0.9600 . ?
C24 H24B 0.9600 . ?
P1 F6 1.514(9) 7_655 ?
P1 F6 1.514(9) . ?
P1 F5 1.525(8) . ?
P1 F5 1.525(8) 7_655 ?
P1 F7 1.526(8) 7_655 ?
P1 F7 1.526(8) . ?
P1 F8 1.531(8) . ?
P1 F8 1.531(8) 7_655 ?
P1 F2 1.539(5) 7_655 ?
P1 F1 1.541(5) 7_655 ?
P2 C21 1.746(10) 7_655 ?
P2 C31 1.753(10) 7_655 ?
P2 C11A 1.800(14) 7_655 ?
P2 C11B 1.806(10) 7_655 ?
F6 F5 1.51(2) . ?
F6 F6 1.74(3) 7_655 ?
F8 F7 1.616(17) . ?
F8 F8 1.75(3) 7_655 ?
F5 F5 1.35(3) 7_655 ?
F7 F7 1.57(3) 7_655 ?

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
C32A C31 P2 121.5(7) . . ?
C32A C31 H31B 107.0 . . ?
P2 C31 H31B 107.0 . . ?
C32A C31 H31A 107.0 . . ?
P2 C31 H31A 107.0 . . ?
H31B C31 H31A 106.7 . . ?
C22A C21 P2 127.9(7) . . ?
C22A C21 H21A 105.3 . . ?
P2 C21 H21A 105.3 . . ?
C22A C21 H21B 105.3 . . ?
P2 C21 H21B 105.3 . . ?
H21A C21 H21B 106.0 . . ?
C33A C34A H34A 109.5 . . ?
C33A C34A H34B 109.5 . . ?
H34A C34A H34B 109.5 . . ?
C33A C34A H34C 109.5 . . ?
H34A C34A H34C 109.5 . . ?
H34B C34A H34C 109.5 . . ?
C14A C13A C12A 96.8(9) . . ?
C14A C13A H13A 112.4 . . ?
C12A C13A H13A 112.4 . . ?
C14A C13A H13B 112.4 . . ?
C12A C13A H13B 112.4 . . ?
H13A C13A H13B 110.0 . . ?
C11B C12B H12C 107.9 . . ?
C11B C12B H12D 107.9 . . ?
H12C C12B H12D 107.2 . . ?
C12B C11B P2 116.0(9) . . ?
C12B C11B H11C 108.3 . . ?
P2 C11B H11C 108.3 . . ?
C12B C11B H11D 108.3 . . ?
P2 C11B H11D 108.3 . . ?
H11C C11B H11D 107.4 . . ?
C12A C11A P2 110.8(10) . . ?
C12A C11A H11A 109.5 . . ?
P2 C11A H11A 109.5 . . ?
C12A C11A H11B 109.5 . . ?
P2 C11A H11B 109.5 . . ?
H11A C11A H11B 108.1 . . ?
C11A C12A C13A 108.4(12) . . ?
C11A C12A H12B 110.0 . . ?
C13A C12A H12B 110.0 . . ?
C11A C12A H12A 110.0 . . ?
C13A C12A H12A 110.0 . . ?
H12B C12A H12A 108.4 . . ?
C24 C23A C22A 138.0(9) . . ?
C24 C23A H23A 102.6 . . ?
C22A C23A H23A 102.6 . . ?
C24 C23A H23B 102.6 . . ?
C22A C23A H23B 102.6 . . ?
H23A C23A H23B 105.0 . . ?
C21 C22A C23A 142.2(8) . . ?
C21 C22A H22A 101.4 . . ?
C23A C22A H22A 101.4 . . ?
C21 C22A H22B 101.4 . . ?
C23A C22A H22B 101.4 . . ?
H22A C22A H22B 104.6 . . ?
C33A C32A C31 136.0(8) . . ?
C33A C32A H32A 103.2 . . ?
C31 C32A H32A 103.2 . . ?
C33A C32A H32B 103.2 . . ?
C31 C32A H32B 103.2 . . ?
H32A C32A H32B 105.2 . . ?
C32A C33A C34A 138.5(13) . . ?
C32A C33A H33A 102.5 . . ?
C34A C33A H33A 102.5 . . ?
C32A C33A H33B 102.5 . . ?
C34A C33A H33B 102.5 . . ?
H33A C33A H33B 104.9 . . ?
F6 P1 F6 69.9(14) 7_655 . ?
F6 P1 F5 90.1(12) 7_655 . ?
F6 P1 F5 59.5(9) . . ?
F6 P1 F5 59.5(9) 7_655 7_655 ?
F6 P1 F5 90.1(12) . 7_655 ?
F5 P1 F5 52.6(12) . 7_655 ?
F6 P1 F7 77.2(13) 7_655 7_655 ?
F6 P1 F7 111.6(9) . 7_655 ?
F5 P1 F7 166.7(14) . 7_655 ?
F5 P1 F7 121.2(9) 7_655 7_655 ?
F6 P1 F7 111.6(9) 7_655 . ?
F6 P1 F7 77.2(13) . . ?
F5 P1 F7 121.2(9) . . ?
F5 P1 F7 166.7(14) 7_655 . ?
F7 P1 F7 61.9(12) 7_655 . ?
F6 P1 F8 174.9(13) 7_655 . ?
F6 P1 F8 110.0(9) . . ?
F5 P1 F8 94.2(12) . . ?
F5 P1 F8 125.4(9) 7_655 . ?
F7 P1 F8 98.4(12) 7_655 . ?
F7 P1 F8 63.8(7) . . ?
F6 P1 F8 110.0(9) 7_655 7_655 ?
F6 P1 F8 174.9(13) . 7_655 ?
F5 P1 F8 125.4(9) . 7_655 ?
F5 P1 F8 94.2(12) 7_655 7_655 ?
F7 P1 F8 63.8(7) 7_655 7_655 ?
F7 P1 F8 98.4(12) . 7_655 ?
F8 P1 F8 69.6(11) . 7_655 ?
F6 P1 F2 141.6(12) 7_655 . ?
F6 P1 F2 87.2(7) . . ?
F5 P1 F2 51.5(9) . . ?
F5 P1 F2 91.3(7) 7_655 . ?
F7 P1 F2 141.1(12) 7_655 . ?
F7 P1 F2 91.8(5) . . ?
F8 P1 F2 42.7(7) . . ?
F8 P1 F2 95.5(6) 7_655 . ?
F6 P1 F2 87.2(7) 7_655 7_655 ?
F6 P1 F2 141.6(12) . 7_655 ?
F5 P1 F2 91.3(7) . 7_655 ?
F5 P1 F2 51.5(9) 7_655 7_655 ?
F7 P1 F2 91.8(5) 7_655 7_655 ?
F7 P1 F2 141.1(12) . 7_655 ?
F8 P1 F2 95.5(6) . 7_655 ?
F8 P1 F2 42.7(8) 7_655 7_655 ?
F2 P1 F2 93.2(6) . 7_655 ?
F6 P1 F1 33.9(10) 7_655 7_655 ?
F6 P1 F1 89.0(7) . 7_655 ?
F5 P1 F1 123.9(11) . 7_655 ?
F5 P1 F1 85.9(6) 7_655 7_655 ?
F7 P1 F1 43.3(9) 7_655 7_655 ?
F7 P1 F1 90.1(5) . 7_655 ?
F8 P1 F1 141.7(11) . 7_655 ?
F8 P1 F1 88.5(5) 7_655 7_655 ?
F2 P1 F1 175.3(7) . 7_655 ?
F2 P1 F1 88.0(4) 7_655 7_655 ?
F6 P1 F1 89.0(7) 7_655 . ?
F6 P1 F1 33.9(10) . . ?
F5 P1 F1 85.9(6) . . ?
F5 P1 F1 123.9(11) 7_655 . ?
F7 P1 F1 90.1(5) 7_655 . ?
F7 P1 F1 43.3(9) . . ?
F8 P1 F1 88.5(5) . . ?
F8 P1 F1 141.7(11) 7_655 . ?
F2 P1 F1 88.0(4) . . ?
F2 P1 F1 175.3(7) 7_655 . ?
F1 P1 F1 90.4(5) 7_655 . ?
C21 P2 C21 41.0(6) 7_655 . ?
C21 P2 C31 97.4(5) 7_655 7_655 ?
C21 P2 C31 114.3(5) . 7_655 ?
C21 P2 C31 114.3(5) 7_655 . ?
C21 P2 C31 97.4(5) . . ?
C31 P2 C31 47.8(7) 7_655 . ?
C21 P2 C11A 110.6(5) 7_655 . ?
C21 P2 C11A 82.0(5) . . ?
C31 P2 C11A 149.5(6) 7_655 . ?
C31 P2 C11A 107.1(5) . . ?
C21 P2 C11A 82.0(5) 7_655 7_655 ?
C21 P2 C11A 110.6(5) . 7_655 ?
C31 P2 C11A 107.1(5) 7_655 7_655 ?
C31 P2 C11A 149.5(6) . 7_655 ?
C11A P2 C11A 89.0(7) . 7_655 ?
C21 P2 C11B 144.1(5) 7_655 . ?
C21 P2 C11B 104.9(4) . . ?
C31 P2 C11B 110.5(5) 7_655 . ?
C31 P2 C11B 73.1(5) . . ?
C11A P2 C11B 39.0(4) . . ?
C11A P2 C11B 109.4(4) 7_655 . ?
C21 P2 C11B 104.9(4) 7_655 7_655 ?
C21 P2 C11B 144.1(5) . 7_655 ?
C31 P2 C11B 73.1(5) 7_655 7_655 ?
C31 P2 C11B 110.5(5) . 7_655 ?
C11A P2 C11B 109.4(4) . 7_655 ?
C11A P2 C11B 39.0(4) 7_655 7_655 ?
C11B P2 C11B 104.5(6) . 7_655 ?
F5 F6 P1 60.6(6) . . ?
F5 F6 F6 82.7(9) . 7_655 ?
P1 F6 F6 55.0(7) . 7_655 ?
P1 F8 F7 57.9(5) . . ?
P1 F8 F8 55.2(5) . 7_655 ?
F7 F8 F8 86.8(7) . 7_655 ?
F5 F5 F6 97.3(9) 7_655 . ?
F5 F5 P1 63.7(6) 7_655 . ?
F6 F5 P1 59.9(5) . . ?
P1 F7 F7 59.1(6) . 7_655 ?
P1 F7 F8 58.3(5) . . ?
F7 F7 F8 93.2(7) 7_655 . ?

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
P2 C11A C12A C13A 164.8(8) . . . . ?
C14A C13A C12A C11A 173.7(11) . . . . ?
P2 C21 C22A C23A 157.9(9) . . . . ?
C24 C23A C22A C21 -159.2(17) . . . . ?
P2 C31 C32A C33A -152.0(9) . . . . ?
C31 C32A C33A C34A -133.4(11) . . . . ?
C22A C21 P2 C21 -26.0(11) . . . 7_655 ?
C22A C21 P2 C31 46.2(12) . . . 7_655 ?
C22A C21 P2 C31 93.0(11) . . . . ?
C22A C21 P2 C11A -160.7(11) . . . . ?
C22A C21 P2 C11A -74.8(11) . . . 7_655 ?
C22A C21 P2 C11B 167.4(10) . . . . ?
C22A C21 P2 C11B -48.5(15) . . . 7_655 ?
C32A C31 P2 C21 -54.1(11) . . . 7_655 ?
C32A C31 P2 C21 -93.1(9) . . . . ?
C32A C31 P2 C31 23.2(10) . . . 7_655 ?
C32A C31 P2 C11A -177.0(8) . . . . ?
C32A C31 P2 C11A 63.9(14) . . . 7_655 ?
C32A C31 P2 C11B 163.5(10) . . . . ?
C32A C31 P2 C11B 63.9(10) . . . 7_655 ?
C12A C11A P2 C21 169.3(9) . . . 7_655 ?
C12A C11A P2 C21 -160.8(10) . . . . ?
C12A C11A P2 C31 -35.2(15) . . . 7_655 ?
C12A C11A P2 C31 -65.5(10) . . . . ?
C12A C11A P2 C11A 88.2(10) . . . 7_655 ?
C12A C11A P2 C11B -35.1(9) . . . . ?
C12A C11A P2 C11B 54.3(11) . . . 7_655 ?
C12B C11B P2 C21 46.5(13) . . . 7_655 ?
C12B C11B P2 C21 61.5(10) . . . . ?
C12B C11B P2 C31 -174.9(9) . . . 7_655 ?
C12B C11B P2 C31 154.8(10) . . . . ?
C12B C11B P2 C11A 5.2(8) . . . . ?
C12B C11B P2 C11A -57.2(10) . . . 7_655 ?
C12B C11B P2 C11B -97.8(9) . . . 7_655 ?
F6 P1 F6 F5 -102.5(10) 7_655 . . . ?
F5 P1 F6 F5 -45.2(12) 7_655 . . . ?
F7 P1 F6 F5 -169.0(14) 7_655 . . . ?
F7 P1 F6 F5 138.5(12) . . . . ?
F8 P1 F6 F5 82.9(16) . . . . ?
F8 P1 F6 F5 168(9) 7_655 . . . ?
F2 P1 F6 F5 46.1(11) . . . . ?
F2 P1 F6 F5 -45.5(14) 7_655 . . . ?
F1 P1 F6 F5 -131.1(12) 7_655 . . . ?
F1 P1 F6 F5 136.8(15) . . . . ?
F5 P1 F6 F6 102.5(10) . . . 7_655 ?
F5 P1 F6 F6 57.3(7) 7_655 . . 7_655 ?
F7 P1 F6 F6 -66.5(10) 7_655 . . 7_655 ?
F7 P1 F6 F6 -119.0(7) . . . 7_655 ?
F8 P1 F6 F6 -174.6(14) . . . 7_655 ?
F8 P1 F6 F6 -90(9) 7_655 . . 7_655 ?
F2 P1 F6 F6 148.6(8) . . . 7_655 ?
F2 P1 F6 F6 57.0(8) 7_655 . . 7_655 ?
F1 P1 F6 F6 -28.6(7) 7_655 . . 7_655 ?
F1 P1 F6 F6 -120.7(9) . . . 7_655 ?
F6 P1 F8 F7 -24(10) 7_655 . . . ?
F6 P1 F8 F7 63.8(15) . . . . ?
F5 P1 F8 F7 122.8(12) . . . . ?
F5 P1 F8 F7 168.8(15) 7_655 . . . ?
F7 P1 F8 F7 -52.9(10) 7_655 . . . ?
F8 P1 F8 F7 -110.8(10) 7_655 . . . ?
F2 P1 F8 F7 125.7(10) . . . . ?
F2 P1 F8 F7 -145.5(11) 7_655 . . . ?
F1 P1 F8 F7 -51.7(11) 7_655 . . . ?
F1 P1 F8 F7 37.0(10) . . . . ?
F6 P1 F8 F8 87(10) 7_655 . . 7_655 ?
F6 P1 F8 F8 174.6(14) . . . 7_655 ?
F5 P1 F8 F8 -126.3(7) . . . 7_655 ?
F5 P1 F8 F8 -80.3(10) 7_655 . . 7_655 ?
F7 P1 F8 F8 58.0(5) 7_655 . . 7_655 ?
F7 P1 F8 F8 110.8(10) . . . 7_655 ?
F2 P1 F8 F8 -123.5(5) . . . 7_655 ?
F2 P1 F8 F8 -34.6(5) 7_655 . . 7_655 ?
F1 P1 F8 F8 59.1(7) 7_655 . . 7_655 ?
F1 P1 F8 F8 147.8(7) . . . 7_655 ?
P1 F6 F5 F5 53.8(6) . . . 7_655 ?
F6 F6 F5 F5 0.000(3) 7_655 . . 7_655 ?
F6 F6 F5 P1 -53.8(6) 7_655 . . . ?
F6 P1 F5 F5 -50.3(6) 7_655 . . 7_655 ?
F6 P1 F5 F5 -116.8(9) . . . 7_655 ?
F7 P1 F5 F5 -66(3) 7_655 . . 7_655 ?
F7 P1 F5 F5 -165.8(13) . . . 7_655 ?
F8 P1 F5 F5 132.5(5) . . . 7_655 ?
F8 P1 F5 F5 64.5(9) 7_655 . . 7_655 ?
F2 P1 F5 F5 130.0(5) . . . 7_655 ?
F2 P1 F5 F5 36.9(5) 7_655 . . 7_655 ?
F1 P1 F5 F5 -51.6(5) 7_655 . . 7_655 ?
F1 P1 F5 F5 -139.3(5) . . . 7_655 ?
F6 P1 F5 F6 66.5(14) 7_655 . . . ?
F5 P1 F5 F6 116.8(10) 7_655 . . . ?
F7 P1 F5 F6 50(3) 7_655 . . . ?
F7 P1 F5 F6 -49.0(17) . . . . ?
F8 P1 F5 F6 -110.7(12) . . . . ?
F8 P1 F5 F6 -178.7(12) 7_655 . . . ?
F2 P1 F5 F6 -113.2(12) . . . . ?
F2 P1 F5 F6 153.7(11) 7_655 . . . ?
F1 P1 F5 F6 65.2(12) 7_655 . . . ?
F1 P1 F5 F6 -22.5(11) . . . . ?
F6 P1 F7 F7 61.2(10) 7_655 . . 7_655 ?
F6 P1 F7 F7 123.3(8) . . . 7_655 ?
F5 P1 F7 F7 165.1(15) . . . 7_655 ?
F5 P1 F7 F7 107(2) 7_655 . . 7_655 ?
F8 P1 F7 F7 -116.6(8) . . . 7_655 ?
F8 P1 F7 F7 -54.2(5) 7_655 . . 7_655 ?
F2 P1 F7 F7 -150.0(7) . . . 7_655 ?
F2 P1 F7 F7 -52.7(6) 7_655 . . 7_655 ?
F1 P1 F7 F7 34.3(5) 7_655 . . 7_655 ?
F1 P1 F7 F7 124.7(6) . . . 7_655 ?
F6 P1 F7 F8 177.8(13) 7_655 . . . ?
F6 P1 F7 F8 -120.2(11) . . . . ?
F5 P1 F7 F8 -78.3(16) . . . . ?
F5 P1 F7 F8 -137(3) 7_655 . . . ?
F7 P1 F7 F8 116.6(8) 7_655 . . . ?
F8 P1 F7 F8 62.3(10) 7_655 . . . ?
F2 P1 F7 F8 -33.5(8) . . . . ?
F2 P1 F7 F8 63.9(12) 7_655 . . . ?
F1 P1 F7 F8 150.9(10) 7_655 . . . ?
F1 P1 F7 F8 -118.7(10) . . . . ?
F8 F8 F7 P1 -50.2(6) 7_655 . . . ?
P1 F8 F7 F7 50.2(6) . . . 7_655 ?
F8 F8 F7 F7 0.000(4) 7_655 . . 7_655 ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.513
_refine_diff_density_min         -0.308
_refine_diff_density_rms         0.062
_database_code_depnum_ccdc_archive 'CCDC 1010903'
