# Supplementary Material (ESI) for Dalton Transactions
# This journal is (c) The Royal Society of Chemistry 2010


data_global
_journal_name_full               'Dalton Trans.'

_journal_coden_Cambridge         0222
_journal_volume                  ?
_journal_page_first              ?
_journal_year                    ?

_publ_contact_author_name        'Jiang, Xin-Dong'
_publ_contact_author_email       xdjiang@henu.edu.cn

_publ_section_title              
;
Efficient synthesis of tetradecafluoro-4-phenylheptan-4-ol
by a Cannizzaro-type reaction and application
of the alcohol as a bulky Martin
ligand variant for a new anti-apicophilic phosphorane
;
loop_
_publ_author_name
X.-D.Jiang
Y.Yamamoto
S.Kojima
S.Matsukawa

# Attachment '- compound_5a.cif'

data_compound5a
#TrackingRef '- compound_5a.cif'

_database_code_depnum_ccdc_archive 'CCDC 778132'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C27 H11 F28 O2 P'
_chemical_formula_weight         930.33

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           ?
_symmetry_space_group_name_H-M   ?

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

_cell_length_a                   9.4620(2)
_cell_length_b                   10.5790(2)
_cell_length_c                   15.9370(3)
_cell_angle_alpha                83.8130(10)
_cell_angle_beta                 89.4400(10)
_cell_angle_gamma                84.8670(10)
_cell_volume                     1579.62(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.956
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             912
_exptl_absorpt_coefficient_mu    0.283
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.9199
_exptl_absorpt_correction_T_max  0.9456
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      173(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_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6994
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0193
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.29
_diffrn_reflns_theta_max         27.92
_reflns_number_total             6994
_reflns_number_gt                6536
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness 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 threshold expression 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
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.1076P)^2^+1.4974P] 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    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         6994
_refine_ls_number_parameters     524
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0534
_refine_ls_R_factor_gt           0.0471
_refine_ls_wR_factor_ref         0.1635
_refine_ls_wR_factor_gt          0.1448
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_restrained_S_all      1.087
_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_symetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.04783(19) -0.05187(18) 0.70894(13) 0.0137(4) Uani 1 1 d . . .
C2 C -0.0874(2) -0.0783(2) 0.68444(14) 0.0193(4) Uani 1 1 d . . .
H2A H -0.1676 -0.0578 0.7183 0.023 Uiso 1 1 calc R . .
C3 C -0.1041(2) -0.1344(2) 0.61089(16) 0.0257(5) Uani 1 1 d . . .
H3A H -0.1958 -0.1529 0.5949 0.031 Uiso 1 1 calc R . .
C4 C 0.0121(3) -0.1636(2) 0.56053(16) 0.0270(5) Uani 1 1 d . . .
H4A H -0.0002 -0.2037 0.5109 0.032 Uiso 1 1 calc R . .
C5 C 0.1464(2) -0.1346(2) 0.58236(15) 0.0231(4) Uani 1 1 d . . .
H5A H 0.2258 -0.1529 0.5473 0.028 Uiso 1 1 calc R . .
C6 C 0.1630(2) -0.07865(18) 0.65611(13) 0.0151(4) Uani 1 1 d . . .
C7 C 0.29768(19) -0.02775(18) 0.68648(13) 0.0139(4) Uani 1 1 d . . .
C8 C 0.32433(19) 0.0912(2) 0.62113(13) 0.0158(4) Uani 1 1 d . . .
C9 C 0.4469(2) 0.1771(2) 0.63273(14) 0.0204(4) Uani 1 1 d . . .
C10 C 0.4210(2) 0.3125(2) 0.58353(16) 0.0263(5) Uani 1 1 d . . .
C11 C 0.4299(2) -0.1265(2) 0.69336(14) 0.0198(4) Uani 1 1 d . . .
C12 C 0.4208(3) -0.2467(2) 0.75801(18) 0.0308(5) Uani 1 1 d . . .
C13 C 0.5344(3) -0.3580(3) 0.7472(2) 0.0366(6) Uani 1 1 d . . .
C14 C -0.09157(19) 0.05758(18) 0.84317(12) 0.0142(4) Uani 1 1 d . . .
C15 C -0.1948(2) -0.0266(2) 0.86675(14) 0.0200(4) Uani 1 1 d . . .
H15A H -0.1751 -0.1154 0.8629 0.024 Uiso 1 1 calc R . .
C16 C -0.3260(2) 0.0204(2) 0.89584(15) 0.0254(5) Uani 1 1 d . . .
H16A H -0.3968 -0.0364 0.9107 0.030 Uiso 1 1 calc R . .
C17 C -0.3545(2) 0.1498(3) 0.90338(15) 0.0271(5) Uani 1 1 d . . .
H17A H -0.4456 0.1810 0.9219 0.033 Uiso 1 1 calc R . .
C18 C -0.2516(2) 0.2341(2) 0.88422(14) 0.0216(4) Uani 1 1 d . . .
H18A H -0.2694 0.3221 0.8913 0.026 Uiso 1 1 calc R . .
C19 C -0.12097(19) 0.18494(19) 0.85420(12) 0.0147(4) Uani 1 1 d . . .
C20 C 0.00756(19) 0.25896(18) 0.83136(12) 0.0128(3) Uani 1 1 d . . .
C21 C -0.0256(2) 0.37353(18) 0.76311(13) 0.0154(4) Uani 1 1 d . . .
C22 C -0.1152(2) 0.34710(19) 0.68624(13) 0.0160(4) Uani 1 1 d . . .
C23 C -0.0948(2) 0.4381(2) 0.60513(14) 0.0207(4) Uani 1 1 d . . .
C24 C 0.0698(2) 0.30022(19) 0.91398(13) 0.0166(4) Uani 1 1 d . . .
C25 C 0.1977(2) 0.3837(2) 0.90950(15) 0.0217(4) Uani 1 1 d . . .
C26 C 0.2741(3) 0.3838(2) 0.99527(17) 0.0290(5) Uani 1 1 d . . .
C27 C 0.1508(2) -0.0822(2) 0.89732(13) 0.0196(4) Uani 1 1 d . . .
H27A H 0.0927 -0.0587 0.9454 0.029 Uiso 1 1 calc R . .
H27B H 0.2505 -0.0719 0.9085 0.029 Uiso 1 1 calc R . .
H27C H 0.1405 -0.1714 0.8890 0.029 Uiso 1 1 calc R . .
O1 O 0.27133(13) 0.01036(13) 0.76552(9) 0.0130(3) Uani 1 1 d . . .
O2 O 0.11436(14) 0.17515(12) 0.79900(9) 0.0125(3) Uani 1 1 d . . .
P1 P 0.09262(5) 0.02048(4) 0.80279(3) 0.01050(13) Uani 1 1 d . . .
F1 F 0.20291(12) 0.17057(12) 0.62111(8) 0.0189(3) Uani 1 1 d . . .
F2 F 0.34045(15) 0.05492(14) 0.54233(8) 0.0252(3) Uani 1 1 d . . .
F3 F 0.56819(14) 0.12220(16) 0.60221(11) 0.0343(4) Uani 1 1 d . . .
F4 F 0.46574(15) 0.19199(15) 0.71409(9) 0.0307(3) Uani 1 1 d . . .
F5 F 0.33015(18) 0.38676(14) 0.62369(12) 0.0377(4) Uani 1 1 d . . .
F6 F 0.37094(18) 0.30693(16) 0.50647(10) 0.0362(4) Uani 1 1 d . . .
F7 F 0.54207(17) 0.36639(18) 0.57612(13) 0.0465(5) Uani 1 1 d . . .
F8 F 0.54277(14) -0.07114(15) 0.71955(11) 0.0313(3) Uani 1 1 d . . .
F9 F 0.46391(16) -0.16478(15) 0.61684(10) 0.0326(3) Uani 1 1 d . . .
F10 F 0.29398(18) -0.28877(18) 0.75788(16) 0.0539(6) Uani 1 1 d . . .
F11 F 0.4415(2) -0.21464(18) 0.83720(11) 0.0457(5) Uani 1 1 d . . .
F12 F 0.6614(2) -0.3193(2) 0.7421(2) 0.0742(8) Uani 1 1 d . . .
F13 F 0.5131(4) -0.4101(2) 0.67785(19) 0.0864(9) Uani 1 1 d . . .
F14 F 0.5284(3) -0.4479(2) 0.80999(18) 0.0694(7) Uani 1 1 d . . .
F15 F 0.09658(13) 0.41721(12) 0.73295(8) 0.0211(3) Uani 1 1 d . . .
F16 F -0.09980(15) 0.46965(12) 0.79892(9) 0.0259(3) Uani 1 1 d . . .
F17 F -0.25344(13) 0.35860(15) 0.70660(9) 0.0271(3) Uani 1 1 d . . .
F18 F -0.08225(14) 0.22741(12) 0.66608(8) 0.0215(3) Uani 1 1 d . . .
F19 F 0.03353(14) 0.41478(15) 0.57325(9) 0.0274(3) Uani 1 1 d . . .
F20 F -0.1135(2) 0.55843(14) 0.62092(11) 0.0398(4) Uani 1 1 d . . .
F21 F -0.18877(15) 0.41829(17) 0.54770(9) 0.0347(4) Uani 1 1 d . . .
F22 F 0.11351(14) 0.18992(12) 0.96267(8) 0.0218(3) Uani 1 1 d . . .
F23 F -0.03354(14) 0.36146(14) 0.95753(9) 0.0252(3) Uani 1 1 d . . .
F24 F 0.15102(17) 0.50517(13) 0.88377(11) 0.0325(3) Uani 1 1 d . . .
F25 F 0.29602(15) 0.34221(15) 0.85526(10) 0.0293(3) Uani 1 1 d . . .
F26 F 0.35730(18) 0.27623(18) 1.01372(11) 0.0409(4) Uani 1 1 d . . .
F27 F 0.18360(18) 0.39459(18) 1.05838(11) 0.0400(4) Uani 1 1 d . . .
F28 F 0.3522(2) 0.4815(2) 0.99113(14) 0.0580(6) Uani 1 1 d . . .

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
C1 0.0137(8) 0.0137(8) 0.0137(9) -0.0020(7) -0.0017(6) -0.0006(6)
C2 0.0153(9) 0.0246(10) 0.0187(10) -0.0023(8) -0.0025(7) -0.0046(7)
C3 0.0243(10) 0.0299(11) 0.0249(12) -0.0051(9) -0.0077(8) -0.0096(8)
C4 0.0344(12) 0.0293(11) 0.0206(11) -0.0116(9) -0.0039(9) -0.0091(9)
C5 0.0266(10) 0.0248(10) 0.0196(11) -0.0101(9) 0.0019(8) -0.0026(8)
C6 0.0167(9) 0.0155(8) 0.0134(9) -0.0040(7) 0.0000(7) -0.0005(6)
C7 0.0118(8) 0.0163(8) 0.0136(9) -0.0043(7) 0.0018(6) 0.0020(6)
C8 0.0114(8) 0.0226(9) 0.0131(9) -0.0034(7) 0.0008(6) 0.0014(7)
C9 0.0121(8) 0.0284(10) 0.0206(10) -0.0011(8) 0.0008(7) -0.0036(7)
C10 0.0186(10) 0.0306(11) 0.0296(12) 0.0017(10) 0.0015(8) -0.0087(8)
C11 0.0149(9) 0.0222(9) 0.0215(11) -0.0048(8) 0.0043(7) 0.0051(7)
C12 0.0230(11) 0.0268(11) 0.0397(14) 0.0025(10) 0.0042(9) 0.0068(9)
C13 0.0390(14) 0.0246(11) 0.0429(16) -0.0025(11) 0.0001(11) 0.0135(10)
C14 0.0126(8) 0.0185(9) 0.0106(9) 0.0006(7) 0.0017(6) 0.0014(6)
C15 0.0178(9) 0.0238(10) 0.0179(10) 0.0007(8) 0.0030(7) -0.0038(7)
C16 0.0152(9) 0.0391(12) 0.0211(11) 0.0022(9) 0.0041(7) -0.0057(8)
C17 0.0133(9) 0.0422(13) 0.0232(11) 0.0012(10) 0.0069(8) 0.0051(9)
C18 0.0165(9) 0.0279(10) 0.0178(10) 0.0005(8) 0.0048(7) 0.0077(8)
C19 0.0121(8) 0.0192(9) 0.0113(9) 0.0010(7) 0.0020(6) 0.0028(7)
C20 0.0123(8) 0.0141(8) 0.0110(9) -0.0015(7) 0.0015(6) 0.0039(6)
C21 0.0175(8) 0.0139(8) 0.0139(9) -0.0011(7) 0.0024(7) 0.0030(6)
C22 0.0133(8) 0.0195(9) 0.0136(9) 0.0027(7) 0.0010(6) 0.0025(7)
C23 0.0181(9) 0.0255(10) 0.0160(10) 0.0065(8) -0.0008(7) 0.0014(7)
C24 0.0201(9) 0.0166(8) 0.0125(9) -0.0037(7) 0.0019(7) 0.0046(7)
C25 0.0249(10) 0.0212(9) 0.0195(11) -0.0064(8) -0.0005(8) 0.0001(8)
C26 0.0294(11) 0.0315(12) 0.0276(13) -0.0127(10) -0.0077(9) 0.0019(9)
C27 0.0207(9) 0.0221(9) 0.0136(9) 0.0031(8) -0.0004(7) 0.0049(7)
O1 0.0099(6) 0.0175(6) 0.0116(7) -0.0045(5) -0.0001(4) 0.0028(5)
O2 0.0118(6) 0.0133(6) 0.0120(6) -0.0027(5) 0.0025(5) 0.0027(5)
P1 0.0092(2) 0.0128(2) 0.0091(2) -0.00092(17) 0.00019(15) 0.00128(15)
F1 0.0104(5) 0.0198(6) 0.0252(7) 0.0013(5) -0.0006(4) 0.0016(4)
F2 0.0325(7) 0.0316(7) 0.0124(6) -0.0064(5) 0.0052(5) -0.0044(5)
F3 0.0127(6) 0.0444(9) 0.0429(9) 0.0025(7) 0.0084(6) 0.0028(6)
F4 0.0305(7) 0.0414(8) 0.0222(7) -0.0020(6) -0.0075(5) -0.0146(6)
F5 0.0394(9) 0.0256(7) 0.0490(10) -0.0076(7) 0.0082(7) -0.0044(6)
F6 0.0446(9) 0.0374(8) 0.0250(8) 0.0068(7) -0.0036(6) -0.0069(7)
F7 0.0256(8) 0.0491(10) 0.0640(12) 0.0131(9) -0.0006(7) -0.0218(7)
F8 0.0151(6) 0.0340(7) 0.0436(9) -0.0057(7) -0.0067(6) 0.0067(5)
F9 0.0304(7) 0.0401(8) 0.0260(8) -0.0137(6) 0.0076(6) 0.0150(6)
F10 0.0257(8) 0.0408(9) 0.0882(16) 0.0270(10) -0.0034(8) -0.0039(7)
F11 0.0582(11) 0.0458(10) 0.0281(9) -0.0005(8) -0.0017(7) 0.0185(8)
F12 0.0320(10) 0.0513(12) 0.129(2) 0.0140(13) 0.0159(12) 0.0225(9)
F13 0.141(3) 0.0417(12) 0.0736(19) -0.0280(12) -0.0115(17) 0.0357(14)
F14 0.0632(13) 0.0375(10) 0.0943(18) 0.0276(11) 0.0158(12) 0.0254(9)
F15 0.0222(6) 0.0219(6) 0.0191(6) 0.0020(5) 0.0003(5) -0.0062(5)
F16 0.0350(7) 0.0176(6) 0.0228(7) -0.0040(5) 0.0014(5) 0.0124(5)
F17 0.0134(6) 0.0434(8) 0.0216(7) 0.0060(6) 0.0027(5) 0.0019(5)
F18 0.0282(6) 0.0185(6) 0.0174(6) -0.0005(5) -0.0044(5) -0.0004(5)
F19 0.0182(6) 0.0428(8) 0.0184(7) 0.0080(6) 0.0033(5) -0.0013(5)
F20 0.0583(11) 0.0208(7) 0.0356(9) 0.0096(6) 0.0023(7) 0.0075(7)
F21 0.0233(7) 0.0580(10) 0.0195(7) 0.0139(7) -0.0079(5) -0.0066(6)
F22 0.0293(7) 0.0216(6) 0.0130(6) 0.0011(5) -0.0044(5) 0.0031(5)
F23 0.0261(7) 0.0317(7) 0.0180(7) -0.0118(6) 0.0046(5) 0.0079(5)
F24 0.0441(9) 0.0192(6) 0.0347(9) -0.0022(6) -0.0090(6) -0.0043(6)
F25 0.0226(6) 0.0422(8) 0.0259(7) -0.0125(6) 0.0058(5) -0.0078(6)
F26 0.0336(8) 0.0503(10) 0.0373(9) -0.0154(8) -0.0144(7) 0.0188(7)
F27 0.0440(9) 0.0529(10) 0.0238(8) -0.0214(8) -0.0064(6) 0.0137(7)
F28 0.0650(13) 0.0611(12) 0.0538(13) -0.0102(10) -0.0238(10) -0.0312(10)

_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
C1 C6 1.398(3) . ?
C1 C2 1.402(3) . ?
C1 P1 1.822(2) . ?
C2 C3 1.386(3) . ?
C3 C4 1.387(4) . ?
C4 C5 1.390(3) . ?
C5 C6 1.388(3) . ?
C6 C7 1.530(3) . ?
C7 O1 1.377(2) . ?
C7 C11 1.553(3) . ?
C7 C8 1.582(3) . ?
C8 F2 1.356(2) . ?
C8 F1 1.361(2) . ?
C8 C9 1.560(3) . ?
C9 F4 1.339(3) . ?
C9 F3 1.349(2) . ?
C9 C10 1.558(3) . ?
C10 F5 1.320(3) . ?
C10 F7 1.323(3) . ?
C10 F6 1.330(3) . ?
C11 F9 1.353(3) . ?
C11 F8 1.354(3) . ?
C11 C12 1.556(3) . ?
C12 F10 1.317(3) . ?
C12 F11 1.362(4) . ?
C12 C13 1.544(3) . ?
C13 F12 1.303(4) . ?
C13 F14 1.309(4) . ?
C13 F13 1.312(4) . ?
C14 C19 1.381(3) . ?
C14 C15 1.401(3) . ?
C14 P1 1.8750(19) . ?
C15 C16 1.390(3) . ?
C16 C17 1.389(4) . ?
C17 C18 1.388(3) . ?
C18 C19 1.398(3) . ?
C19 C20 1.525(3) . ?
C20 O2 1.415(2) . ?
C20 C21 1.551(3) . ?
C20 C24 1.567(3) . ?
C21 F15 1.349(2) . ?
C21 F16 1.357(2) . ?
C21 C22 1.560(3) . ?
C22 F17 1.343(2) . ?
C22 F18 1.349(2) . ?
C22 C23 1.547(3) . ?
C23 F20 1.320(3) . ?
C23 F19 1.325(2) . ?
C23 F21 1.327(3) . ?
C24 F23 1.352(2) . ?
C24 F22 1.364(2) . ?
C24 C25 1.557(3) . ?
C25 F25 1.342(3) . ?
C25 F24 1.342(3) . ?
C25 C26 1.553(3) . ?
C26 F28 1.319(3) . ?
C26 F27 1.322(3) . ?
C26 F26 1.332(3) . ?
C27 P1 1.819(2) . ?
O1 P1 1.7847(14) . ?
O2 P1 1.6620(14) . ?

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 C1 C2 118.56(19) . . ?
C6 C1 P1 114.42(14) . . ?
C2 C1 P1 126.98(16) . . ?
C3 C2 C1 120.1(2) . . ?
C2 C3 C4 120.5(2) . . ?
C3 C4 C5 120.3(2) . . ?
C6 C5 C4 119.1(2) . . ?
C5 C6 C1 121.39(19) . . ?
C5 C6 C7 127.00(19) . . ?
C1 C6 C7 111.38(18) . . ?
O1 C7 C6 108.02(15) . . ?
O1 C7 C11 107.65(16) . . ?
C6 C7 C11 114.49(17) . . ?
O1 C7 C8 110.28(16) . . ?
C6 C7 C8 105.44(15) . . ?
C11 C7 C8 110.91(15) . . ?
F2 C8 F1 107.21(16) . . ?
F2 C8 C9 105.81(16) . . ?
F1 C8 C9 105.34(16) . . ?
F2 C8 C7 110.19(17) . . ?
F1 C8 C7 105.48(14) . . ?
C9 C8 C7 121.96(16) . . ?
F4 C9 F3 108.94(18) . . ?
F4 C9 C10 107.64(19) . . ?
F3 C9 C10 106.73(17) . . ?
F4 C9 C8 111.52(17) . . ?
F3 C9 C8 108.98(18) . . ?
C10 C9 C8 112.85(17) . . ?
F5 C10 F7 108.0(2) . . ?
F5 C10 F6 108.4(2) . . ?
F7 C10 F6 108.2(2) . . ?
F5 C10 C9 111.22(19) . . ?
F7 C10 C9 109.50(19) . . ?
F6 C10 C9 111.4(2) . . ?
F9 C11 F8 106.84(17) . . ?
F9 C11 C7 110.47(18) . . ?
F8 C11 C7 109.50(17) . . ?
F9 C11 C12 108.75(19) . . ?
F8 C11 C12 104.13(19) . . ?
C7 C11 C12 116.58(17) . . ?
F10 C12 F11 106.5(2) . . ?
F10 C12 C13 109.3(2) . . ?
F11 C12 C13 105.1(2) . . ?
F10 C12 C11 111.3(2) . . ?
F11 C12 C11 109.1(2) . . ?
C13 C12 C11 115.1(2) . . ?
F12 C13 F14 109.8(3) . . ?
F12 C13 F13 107.1(3) . . ?
F14 C13 F13 106.9(3) . . ?
F12 C13 C12 111.5(2) . . ?
F14 C13 C12 110.3(2) . . ?
F13 C13 C12 111.1(3) . . ?
C19 C14 C15 118.49(18) . . ?
C19 C14 P1 112.79(14) . . ?
C15 C14 P1 128.62(16) . . ?
C16 C15 C14 119.7(2) . . ?
C17 C16 C15 120.5(2) . . ?
C18 C17 C16 120.80(19) . . ?
C17 C18 C19 117.7(2) . . ?
C14 C19 C18 122.67(19) . . ?
C14 C19 C20 110.72(16) . . ?
C18 C19 C20 126.59(19) . . ?
O2 C20 C19 108.33(15) . . ?
O2 C20 C21 107.75(15) . . ?
C19 C20 C21 112.94(15) . . ?
O2 C20 C24 106.20(15) . . ?
C19 C20 C24 108.92(15) . . ?
C21 C20 C24 112.40(16) . . ?
F15 C21 F16 107.62(16) . . ?
F15 C21 C20 109.68(15) . . ?
F16 C21 C20 109.09(15) . . ?
F15 C21 C22 107.73(16) . . ?
F16 C21 C22 106.36(16) . . ?
C20 C21 C22 116.02(16) . . ?
F17 C22 F18 107.95(17) . . ?
F17 C22 C23 107.68(15) . . ?
F18 C22 C23 106.71(17) . . ?
F17 C22 C21 109.16(17) . . ?
F18 C22 C21 110.80(15) . . ?
C23 C22 C21 114.31(17) . . ?
F20 C23 F19 109.56(19) . . ?
F20 C23 F21 108.98(18) . . ?
F19 C23 F21 107.77(19) . . ?
F20 C23 C22 110.77(19) . . ?
F19 C23 C22 110.54(16) . . ?
F21 C23 C22 109.16(18) . . ?
F23 C24 F22 106.82(16) . . ?
F23 C24 C25 106.48(17) . . ?
F22 C24 C25 106.06(16) . . ?
F23 C24 C20 110.24(16) . . ?
F22 C24 C20 106.07(16) . . ?
C25 C24 C20 120.40(17) . . ?
F25 C25 F24 109.34(19) . . ?
F25 C25 C26 106.61(18) . . ?
F24 C25 C26 107.15(19) . . ?
F25 C25 C24 110.62(18) . . ?
F24 C25 C24 109.01(17) . . ?
C26 C25 C24 113.96(19) . . ?
F28 C26 F27 107.8(2) . . ?
F28 C26 F26 109.1(2) . . ?
F27 C26 F26 107.4(2) . . ?
F28 C26 C25 109.2(2) . . ?
F27 C26 C25 112.2(2) . . ?
F26 C26 C25 111.0(2) . . ?
C7 O1 P1 118.36(12) . . ?
C20 O2 P1 119.75(11) . . ?
O2 P1 O1 83.26(6) . . ?
O2 P1 C27 117.99(9) . . ?
O1 P1 C27 89.00(8) . . ?
O2 P1 C1 121.61(8) . . ?
O1 P1 C1 86.73(8) . . ?
C27 P1 C1 119.17(10) . . ?
O2 P1 C14 87.97(8) . . ?
O1 P1 C14 171.20(8) . . ?
C27 P1 C14 94.39(9) . . ?
C1 P1 C14 98.64(9) . . ?

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
C6 C1 C2 C3 2.4(3) . . . . ?
P1 C1 C2 C3 -179.80(17) . . . . ?
C1 C2 C3 C4 -0.6(3) . . . . ?
C2 C3 C4 C5 -1.3(4) . . . . ?
C3 C4 C5 C6 1.4(4) . . . . ?
C4 C5 C6 C1 0.5(3) . . . . ?
C4 C5 C6 C7 -173.4(2) . . . . ?
C2 C1 C6 C5 -2.4(3) . . . . ?
P1 C1 C6 C5 179.57(16) . . . . ?
C2 C1 C6 C7 172.41(17) . . . . ?
P1 C1 C6 C7 -5.6(2) . . . . ?
C5 C6 C7 O1 -175.27(19) . . . . ?
C1 C6 C7 O1 10.3(2) . . . . ?
C5 C6 C7 C11 -55.4(3) . . . . ?
C1 C6 C7 C11 130.18(18) . . . . ?
C5 C6 C7 C8 66.8(2) . . . . ?
C1 C6 C7 C8 -107.63(18) . . . . ?
O1 C7 C8 F2 -175.77(14) . . . . ?
C6 C7 C8 F2 -59.39(19) . . . . ?
C11 C7 C8 F2 65.1(2) . . . . ?
O1 C7 C8 F1 -60.38(19) . . . . ?
C6 C7 C8 F1 56.00(19) . . . . ?
C11 C7 C8 F1 -179.54(16) . . . . ?
O1 C7 C8 C9 59.4(2) . . . . ?
C6 C7 C8 C9 175.76(17) . . . . ?
C11 C7 C8 C9 -59.8(2) . . . . ?
F2 C8 C9 F4 -163.82(17) . . . . ?
F1 C8 C9 F4 82.8(2) . . . . ?
C7 C8 C9 F4 -37.0(3) . . . . ?
F2 C8 C9 F3 -43.5(2) . . . . ?
F1 C8 C9 F3 -156.86(16) . . . . ?
C7 C8 C9 F3 83.3(2) . . . . ?
F2 C8 C9 C10 74.9(2) . . . . ?
F1 C8 C9 C10 -38.5(2) . . . . ?
C7 C8 C9 C10 -158.31(18) . . . . ?
F4 C9 C10 F5 -45.2(2) . . . . ?
F3 C9 C10 F5 -162.03(19) . . . . ?
C8 C9 C10 F5 78.3(2) . . . . ?
F4 C9 C10 F7 74.0(2) . . . . ?
F3 C9 C10 F7 -42.8(3) . . . . ?
C8 C9 C10 F7 -162.5(2) . . . . ?
F4 C9 C10 F6 -166.31(17) . . . . ?
F3 C9 C10 F6 76.9(2) . . . . ?
C8 C9 C10 F6 -42.8(3) . . . . ?
O1 C7 C11 F9 -178.10(16) . . . . ?
C6 C7 C11 F9 61.8(2) . . . . ?
C8 C7 C11 F9 -57.4(2) . . . . ?
O1 C7 C11 F8 -60.7(2) . . . . ?
C6 C7 C11 F8 179.19(17) . . . . ?
C8 C7 C11 F8 60.0(2) . . . . ?
O1 C7 C11 C12 57.1(2) . . . . ?
C6 C7 C11 C12 -63.0(3) . . . . ?
C8 C7 C11 C12 177.85(19) . . . . ?
F9 C11 C12 F10 -86.1(2) . . . . ?
F8 C11 C12 F10 160.3(2) . . . . ?
C7 C11 C12 F10 39.6(3) . . . . ?
F9 C11 C12 F11 156.74(19) . . . . ?
F8 C11 C12 F11 43.1(2) . . . . ?
C7 C11 C12 F11 -77.6(2) . . . . ?
F9 C11 C12 C13 39.0(3) . . . . ?
F8 C11 C12 C13 -74.7(3) . . . . ?
C7 C11 C12 C13 164.6(2) . . . . ?
F10 C12 C13 F12 176.3(3) . . . . ?
F11 C12 C13 F12 -69.7(3) . . . . ?
C11 C12 C13 F12 50.3(4) . . . . ?
F10 C12 C13 F14 -61.3(4) . . . . ?
F11 C12 C13 F14 52.6(3) . . . . ?
C11 C12 C13 F14 172.6(3) . . . . ?
F10 C12 C13 F13 57.0(3) . . . . ?
F11 C12 C13 F13 170.9(3) . . . . ?
C11 C12 C13 F13 -69.1(3) . . . . ?
C19 C14 C15 C16 3.7(3) . . . . ?
P1 C14 C15 C16 179.66(17) . . . . ?
C14 C15 C16 C17 -1.4(4) . . . . ?
C15 C16 C17 C18 -1.7(4) . . . . ?
C16 C17 C18 C19 2.4(3) . . . . ?
C15 C14 C19 C18 -3.0(3) . . . . ?
P1 C14 C19 C18 -179.63(16) . . . . ?
C15 C14 C19 C20 175.67(18) . . . . ?
P1 C14 C19 C20 -0.9(2) . . . . ?
C17 C18 C19 C14 0.0(3) . . . . ?
C17 C18 C19 C20 -178.5(2) . . . . ?
C14 C19 C20 O2 4.8(2) . . . . ?
C18 C19 C20 O2 -176.58(19) . . . . ?
C14 C19 C20 C21 124.06(18) . . . . ?
C18 C19 C20 C21 -57.3(3) . . . . ?
C14 C19 C20 C24 -110.31(18) . . . . ?
C18 C19 C20 C24 68.3(2) . . . . ?
O2 C20 C21 F15 -47.2(2) . . . . ?
C19 C20 C21 F15 -166.81(16) . . . . ?
C24 C20 C21 F15 69.5(2) . . . . ?
O2 C20 C21 F16 -164.85(16) . . . . ?
C19 C20 C21 F16 75.5(2) . . . . ?
C24 C20 C21 F16 -48.2(2) . . . . ?
O2 C20 C21 C22 75.1(2) . . . . ?
C19 C20 C21 C22 -44.5(2) . . . . ?
C24 C20 C21 C22 -168.23(16) . . . . ?
F15 C21 C22 F17 -153.12(15) . . . . ?
F16 C21 C22 F17 -38.0(2) . . . . ?
C20 C21 C22 F17 83.5(2) . . . . ?
F15 C21 C22 F18 88.13(18) . . . . ?
F16 C21 C22 F18 -156.71(15) . . . . ?
C20 C21 C22 F18 -35.2(2) . . . . ?
F15 C21 C22 C23 -32.5(2) . . . . ?
F16 C21 C22 C23 82.7(2) . . . . ?
C20 C21 C22 C23 -155.80(16) . . . . ?
F17 C22 C23 F20 69.6(2) . . . . ?
F18 C22 C23 F20 -174.74(17) . . . . ?
C21 C22 C23 F20 -51.9(2) . . . . ?
F17 C22 C23 F19 -168.78(19) . . . . ?
F18 C22 C23 F19 -53.1(2) . . . . ?
C21 C22 C23 F19 69.7(2) . . . . ?
F17 C22 C23 F21 -50.4(2) . . . . ?
F18 C22 C23 F21 65.3(2) . . . . ?
C21 C22 C23 F21 -171.89(17) . . . . ?
O2 C20 C24 F23 -168.78(15) . . . . ?
C19 C20 C24 F23 -52.3(2) . . . . ?
C21 C20 C24 F23 73.6(2) . . . . ?
O2 C20 C24 F22 -53.48(18) . . . . ?
C19 C20 C24 F22 62.98(18) . . . . ?
C21 C20 C24 F22 -171.08(14) . . . . ?
O2 C20 C24 C25 66.7(2) . . . . ?
C19 C20 C24 C25 -176.83(16) . . . . ?
C21 C20 C24 C25 -50.9(2) . . . . ?
F23 C24 C25 F25 -169.37(17) . . . . ?
F22 C24 C25 F25 77.1(2) . . . . ?
C20 C24 C25 F25 -43.1(2) . . . . ?
F23 C24 C25 F24 -49.1(2) . . . . ?
F22 C24 C25 F24 -162.63(17) . . . . ?
C20 C24 C25 F24 77.2(2) . . . . ?
F23 C24 C25 C26 70.5(2) . . . . ?
F22 C24 C25 C26 -43.0(2) . . . . ?
C20 C24 C25 C26 -163.18(18) . . . . ?
F25 C25 C26 F28 75.0(3) . . . . ?
F24 C25 C26 F28 -42.0(3) . . . . ?
C24 C25 C26 F28 -162.7(2) . . . . ?
F25 C25 C26 F27 -165.5(2) . . . . ?
F24 C25 C26 F27 77.5(3) . . . . ?
C24 C25 C26 F27 -43.2(3) . . . . ?
F25 C25 C26 F26 -45.3(3) . . . . ?
F24 C25 C26 F26 -162.3(2) . . . . ?
C24 C25 C26 F26 77.0(3) . . . . ?
C6 C7 O1 P1 -11.19(19) . . . . ?
C11 C7 O1 P1 -135.32(13) . . . . ?
C8 C7 O1 P1 103.56(15) . . . . ?
C19 C20 O2 P1 -7.5(2) . . . . ?
C21 C20 O2 P1 -129.96(14) . . . . ?
C24 C20 O2 P1 109.40(15) . . . . ?
C20 O2 P1 O1 -173.21(14) . . . . ?
C20 O2 P1 C27 -87.95(15) . . . . ?
C20 O2 P1 C1 104.86(15) . . . . ?
C20 O2 P1 C14 5.95(14) . . . . ?
C7 O1 P1 O2 -115.24(14) . . . . ?
C7 O1 P1 C27 126.42(15) . . . . ?
C7 O1 P1 C1 7.13(14) . . . . ?
C7 O1 P1 C14 -120.8(5) . . . . ?
C6 C1 P1 O2 79.76(16) . . . . ?
C2 C1 P1 O2 -98.07(18) . . . . ?
C6 C1 P1 O1 -0.26(14) . . . . ?
C2 C1 P1 O1 -178.10(18) . . . . ?
C6 C1 P1 C27 -87.29(16) . . . . ?
C2 C1 P1 C27 94.88(19) . . . . ?
C6 C1 P1 C14 172.72(14) . . . . ?
C2 C1 P1 C14 -5.12(19) . . . . ?
C19 C14 P1 O2 -2.57(15) . . . . ?
C15 C14 P1 O2 -178.8(2) . . . . ?
C19 C14 P1 O1 2.9(6) . . . . ?
C15 C14 P1 O1 -173.3(4) . . . . ?
C19 C14 P1 C27 115.36(16) . . . . ?
C15 C14 P1 C27 -60.8(2) . . . . ?
C19 C14 P1 C1 -124.24(15) . . . . ?
C15 C14 P1 C1 59.6(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.923
_diffrn_reflns_theta_full        27.92
_diffrn_measured_fraction_theta_full 0.923
_refine_diff_density_max         1.367
_refine_diff_density_min         -0.661
_refine_diff_density_rms         0.180

# Attachment '- compound_6a.cif'

data_compound6a
#TrackingRef '- compound_6a.cif'

_database_code_depnum_ccdc_archive 'CCDC 778133'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C27 H11 F28 O2 P'
_chemical_formula_weight         930.33

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           ?
_symmetry_space_group_name_H-M   ?

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

_cell_length_a                   23.7910(4)
_cell_length_b                   11.5480(2)
_cell_length_c                   11.9090(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 99.8000(10)
_cell_angle_gamma                90.00
_cell_volume                     3224.12(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.917
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1824
_exptl_absorpt_coefficient_mu    0.277
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.8513
_exptl_absorpt_correction_T_max  0.9466
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      200(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_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            3848
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0159
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.74
_diffrn_reflns_theta_max         27.88
_reflns_number_total             3848
_reflns_number_gt                3481
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness 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 threshold expression 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
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0987P)^2^+5.4591P] 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    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3848
_refine_ls_number_parameters     260
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0615
_refine_ls_R_factor_gt           0.0535
_refine_ls_wR_factor_ref         0.1704
_refine_ls_wR_factor_gt          0.1524
_refine_ls_goodness_of_fit_ref   1.158
_refine_ls_restrained_S_all      1.158
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.99577(8) 0.79702(17) 0.61090(16) 0.0184(4) Uani 1 1 d . . .
C2 C 1.04146(9) 0.7644(2) 0.55767(18) 0.0248(4) Uani 1 1 d . . .
H1 H 1.0796 0.7778 0.5940 0.030 Uiso 1 1 calc R . .
C3 C 1.03043(11) 0.7122(2) 0.4513(2) 0.0330(5) Uani 1 1 d . . .
H2 H 1.0613 0.6886 0.4155 0.040 Uiso 1 1 calc R . .
C4 C 0.97481(11) 0.6942(3) 0.39666(19) 0.0345(5) Uani 1 1 d . . .
H3 H 0.9680 0.6577 0.3241 0.041 Uiso 1 1 calc R . .
C5 C 0.92898(10) 0.7290(2) 0.44695(18) 0.0282(5) Uani 1 1 d . . .
H4 H 0.8909 0.7187 0.4088 0.034 Uiso 1 1 calc R . .
C6 C 0.94035(8) 0.77937(17) 0.55444(16) 0.0195(4) Uani 1 1 d . . .
C7 C 0.89589(8) 0.82123(17) 0.62372(16) 0.0177(4) Uani 1 1 d . . .
C8 C 0.85313(8) 0.72452(18) 0.64497(17) 0.0206(4) Uani 1 1 d . . .
C9 C 0.87797(9) 0.60098(18) 0.67241(18) 0.0243(4) Uani 1 1 d . . .
C10 C 0.84150(11) 0.5235(2) 0.7375(2) 0.0351(5) Uani 1 1 d . . .
C11 C 0.86383(9) 0.92784(19) 0.55936(17) 0.0222(4) Uani 1 1 d . . .
C12 C 0.81919(9) 0.9939(2) 0.6158(2) 0.0294(5) Uani 1 1 d . . .
C13 C 0.80455(13) 1.1168(2) 0.5665(3) 0.0440(7) Uani 1 1 d . . .
P1 P 1.0000 0.86593(6) 0.7500 0.01612(18) Uani 1 2 d S . .
O1 O 0.92509(6) 0.85855(13) 0.72827(11) 0.0195(3) Uani 1 1 d . . .
F1 F 0.81147(6) 0.71169(13) 0.55342(12) 0.0328(3) Uani 1 1 d . . .
F2 F 0.82777(6) 0.75684(12) 0.73385(12) 0.0300(3) Uani 1 1 d . . .
F3 F 0.93059(6) 0.60616(12) 0.73535(13) 0.0328(3) Uani 1 1 d . . .
F4 F 0.88192(8) 0.54611(13) 0.57459(13) 0.0400(4) Uani 1 1 d . . .
F5 F 0.78682(7) 0.52917(17) 0.69216(18) 0.0518(5) Uani 1 1 d . . .
F6 F 0.84751(9) 0.55339(17) 0.84579(15) 0.0511(5) Uani 1 1 d . . .
F7 F 0.85889(9) 0.41377(14) 0.73255(19) 0.0545(5) Uani 1 1 d . . .
F8 F 0.83758(6) 0.89741(13) 0.45388(11) 0.0337(3) Uani 1 1 d . . .
F9 F 0.90491(6) 1.00582(12) 0.54494(12) 0.0310(3) Uani 1 1 d . . .
F10 F 0.83607(8) 1.00481(17) 0.72726(14) 0.0466(4) Uani 1 1 d . . .
F11 F 0.76979(6) 0.93366(14) 0.59789(17) 0.0434(4) Uani 1 1 d . . .
F12 F 0.79739(13) 1.1177(2) 0.4543(2) 0.0769(7) Uani 1 1 d . . .
F13 F 0.84687(10) 1.18913(17) 0.6025(3) 0.0777(8) Uani 1 1 d . . .
F14 F 0.75974(10) 1.15690(18) 0.6036(3) 0.0770(8) Uani 1 1 d . . .
C14 C 1.0000 1.0225(3) 0.7500 0.0316(7) Uiso 1 2 d S . .

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
C1 0.0172(8) 0.0200(9) 0.0181(8) 0.0018(7) 0.0035(7) -0.0008(7)
C2 0.0197(9) 0.0334(11) 0.0227(9) 0.0010(8) 0.0078(7) -0.0006(8)
C3 0.0287(11) 0.0458(14) 0.0275(11) -0.0059(10) 0.0132(9) 0.0001(10)
C4 0.0336(12) 0.0507(15) 0.0209(10) -0.0109(10) 0.0091(9) -0.0058(10)
C5 0.0242(10) 0.0391(12) 0.0209(9) -0.0061(9) 0.0028(8) -0.0044(9)
C6 0.0180(9) 0.0228(9) 0.0180(8) 0.0001(7) 0.0039(7) -0.0003(7)
C7 0.0150(8) 0.0198(8) 0.0174(8) 0.0001(7) 0.0001(6) 0.0008(6)
C8 0.0166(9) 0.0226(9) 0.0218(9) 0.0005(7) 0.0011(7) 0.0003(7)
C9 0.0225(10) 0.0220(10) 0.0274(10) -0.0006(8) 0.0017(8) 0.0002(7)
C10 0.0323(12) 0.0288(11) 0.0431(13) 0.0118(10) 0.0028(10) -0.0024(9)
C11 0.0176(9) 0.0245(9) 0.0233(9) 0.0035(7) -0.0002(7) 0.0000(7)
C12 0.0219(10) 0.0277(11) 0.0380(12) 0.0041(9) 0.0037(8) 0.0056(8)
C13 0.0365(14) 0.0263(11) 0.0695(19) 0.0087(12) 0.0100(13) 0.0074(10)
P1 0.0153(3) 0.0151(3) 0.0173(3) 0.000 0.0008(2) 0.000
O1 0.0154(6) 0.0243(7) 0.0177(6) -0.0040(5) 0.0002(5) 0.0027(5)
F1 0.0229(7) 0.0332(7) 0.0367(7) 0.0064(6) -0.0106(5) -0.0077(5)
F2 0.0262(7) 0.0297(7) 0.0380(7) 0.0016(5) 0.0168(6) 0.0019(5)
F3 0.0216(6) 0.0285(7) 0.0453(8) 0.0042(6) -0.0031(6) 0.0039(5)
F4 0.0587(10) 0.0278(7) 0.0348(8) -0.0085(6) 0.0117(7) 0.0015(7)
F5 0.0295(8) 0.0507(10) 0.0720(12) 0.0209(9) -0.0002(8) -0.0137(7)
F6 0.0585(11) 0.0603(11) 0.0367(9) 0.0155(8) 0.0145(8) -0.0020(9)
F7 0.0642(12) 0.0249(8) 0.0732(13) 0.0157(8) 0.0083(10) -0.0009(7)
F8 0.0353(8) 0.0382(8) 0.0233(6) 0.0056(6) -0.0075(5) 0.0026(6)
F9 0.0246(6) 0.0271(7) 0.0416(8) 0.0109(6) 0.0063(5) -0.0016(5)
F10 0.0481(9) 0.0559(10) 0.0356(8) -0.0058(7) 0.0068(7) 0.0243(8)
F11 0.0225(7) 0.0346(8) 0.0743(12) 0.0051(7) 0.0117(7) 0.0012(6)
F12 0.1034(19) 0.0548(12) 0.0685(14) 0.0309(11) 0.0035(13) 0.0285(12)
F13 0.0613(13) 0.0270(9) 0.149(2) -0.0102(11) 0.0294(14) -0.0064(9)
F14 0.0554(13) 0.0449(11) 0.140(2) 0.0315(12) 0.0431(14) 0.0320(9)

_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
C1 C6 1.390(3) . ?
C1 C2 1.400(3) . ?
C1 P1 1.8250(19) . ?
C2 C3 1.387(3) . ?
C3 C4 1.387(3) . ?
C4 C5 1.390(3) . ?
C5 C6 1.390(3) . ?
C6 C7 1.527(3) . ?
C7 O1 1.387(2) . ?
C7 C8 1.560(3) . ?
C7 C11 1.577(3) . ?
C8 F1 1.351(2) . ?
C8 F2 1.357(2) . ?
C8 C9 1.557(3) . ?
C9 F4 1.343(3) . ?
C9 F3 1.347(2) . ?
C9 C10 1.543(3) . ?
C10 F6 1.320(3) . ?
C10 F5 1.322(3) . ?
C10 F7 1.337(3) . ?
C11 F8 1.351(2) . ?
C11 F9 1.361(2) . ?
C11 C12 1.551(3) . ?
C12 F10 1.326(3) . ?
C12 F11 1.351(3) . ?
C12 C13 1.553(3) . ?
C13 F14 1.307(4) . ?
C13 F12 1.317(4) . ?
C13 F13 1.322(4) . ?
P1 O1 1.7588(14) . ?
P1 O1 1.7588(14) 2_756 ?
P1 C14 1.808(4) . ?
P1 C1 1.8251(19) 2_756 ?

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 C1 C2 119.17(18) . . ?
C6 C1 P1 113.85(14) . . ?
C2 C1 P1 126.96(15) . . ?
C3 C2 C1 119.3(2) . . ?
C2 C3 C4 120.7(2) . . ?
C3 C4 C5 120.7(2) . . ?
C4 C5 C6 118.3(2) . . ?
C1 C6 C5 121.79(18) . . ?
C1 C6 C7 112.32(16) . . ?
C5 C6 C7 125.89(18) . . ?
O1 C7 C6 107.23(15) . . ?
O1 C7 C8 108.52(15) . . ?
C6 C7 C8 113.07(16) . . ?
O1 C7 C11 108.71(16) . . ?
C6 C7 C11 107.88(15) . . ?
C8 C7 C11 111.29(15) . . ?
F1 C8 F2 107.28(16) . . ?
F1 C8 C9 105.60(16) . . ?
F2 C8 C9 106.95(16) . . ?
F1 C8 C7 110.90(16) . . ?
F2 C8 C7 108.57(16) . . ?
C9 C8 C7 117.09(16) . . ?
F4 C9 F3 107.94(18) . . ?
F4 C9 C10 106.86(19) . . ?
F3 C9 C10 107.17(18) . . ?
F4 C9 C8 109.28(17) . . ?
F3 C9 C8 111.08(17) . . ?
C10 C9 C8 114.25(18) . . ?
F6 C10 F5 108.7(2) . . ?
F6 C10 F7 107.9(2) . . ?
F5 C10 F7 108.6(2) . . ?
F6 C10 C9 111.2(2) . . ?
F5 C10 C9 111.4(2) . . ?
F7 C10 C9 108.8(2) . . ?
F8 C11 F9 106.44(17) . . ?
F8 C11 C12 106.79(17) . . ?
F9 C11 C12 106.78(18) . . ?
F8 C11 C7 110.96(17) . . ?
F9 C11 C7 106.24(15) . . ?
C12 C11 C7 118.93(17) . . ?
F10 C12 F11 108.3(2) . . ?
F10 C12 C11 111.57(18) . . ?
F11 C12 C11 108.65(19) . . ?
F10 C12 C13 107.6(2) . . ?
F11 C12 C13 106.13(19) . . ?
C11 C12 C13 114.3(2) . . ?
F14 C13 F12 111.6(3) . . ?
F14 C13 F13 106.6(3) . . ?
F12 C13 F13 106.5(3) . . ?
F14 C13 C12 109.8(2) . . ?
F12 C13 C12 111.9(2) . . ?
F13 C13 C12 110.2(2) . . ?
O1 P1 O1 174.44(10) . 2_756 ?
O1 P1 C14 92.78(5) . . ?
O1 P1 C14 92.78(5) 2_756 . ?
O1 P1 C1 86.99(7) . . ?
O1 P1 C1 90.59(8) 2_756 . ?
C14 P1 C1 115.85(6) . . ?
O1 P1 C1 90.59(8) . 2_756 ?
O1 P1 C1 86.99(7) 2_756 2_756 ?
C14 P1 C1 115.85(6) . 2_756 ?
C1 P1 C1 128.30(13) . 2_756 ?
C7 O1 P1 119.16(12) . . ?

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
C6 C1 C2 C3 -1.8(3) . . . . ?
P1 C1 C2 C3 179.76(18) . . . . ?
C1 C2 C3 C4 1.2(4) . . . . ?
C2 C3 C4 C5 0.6(4) . . . . ?
C3 C4 C5 C6 -1.7(4) . . . . ?
C2 C1 C6 C5 0.7(3) . . . . ?
P1 C1 C6 C5 179.32(17) . . . . ?
C2 C1 C6 C7 -179.21(18) . . . . ?
P1 C1 C6 C7 -0.6(2) . . . . ?
C4 C5 C6 C1 1.1(3) . . . . ?
C4 C5 C6 C7 -179.0(2) . . . . ?
C1 C6 C7 O1 -3.9(2) . . . . ?
C5 C6 C7 O1 176.2(2) . . . . ?
C1 C6 C7 C8 -123.44(18) . . . . ?
C5 C6 C7 C8 56.7(3) . . . . ?
C1 C6 C7 C11 113.06(18) . . . . ?
C5 C6 C7 C11 -66.8(3) . . . . ?
O1 C7 C8 F1 159.87(16) . . . . ?
C6 C7 C8 F1 -81.3(2) . . . . ?
C11 C7 C8 F1 40.3(2) . . . . ?
O1 C7 C8 F2 42.2(2) . . . . ?
C6 C7 C8 F2 161.07(16) . . . . ?
C11 C7 C8 F2 -77.33(19) . . . . ?
O1 C7 C8 C9 -78.9(2) . . . . ?
C6 C7 C8 C9 39.9(2) . . . . ?
C11 C7 C8 C9 161.53(17) . . . . ?
F1 C8 C9 F4 40.6(2) . . . . ?
F2 C8 C9 F4 154.65(17) . . . . ?
C7 C8 C9 F4 -83.4(2) . . . . ?
F1 C8 C9 F3 159.58(17) . . . . ?
F2 C8 C9 F3 -86.4(2) . . . . ?
C7 C8 C9 F3 35.6(2) . . . . ?
F1 C8 C9 C10 -79.0(2) . . . . ?
F2 C8 C9 C10 35.0(2) . . . . ?
C7 C8 C9 C10 156.99(19) . . . . ?
F4 C9 C10 F6 163.3(2) . . . . ?
F3 C9 C10 F6 47.8(3) . . . . ?
C8 C9 C10 F6 -75.7(3) . . . . ?
F4 C9 C10 F5 -75.2(3) . . . . ?
F3 C9 C10 F5 169.3(2) . . . . ?
C8 C9 C10 F5 45.7(3) . . . . ?
F4 C9 C10 F7 44.5(3) . . . . ?
F3 C9 C10 F7 -71.0(2) . . . . ?
C8 C9 C10 F7 165.47(19) . . . . ?
O1 C7 C11 F8 176.16(16) . . . . ?
C6 C7 C11 F8 60.2(2) . . . . ?
C8 C7 C11 F8 -64.4(2) . . . . ?
O1 C7 C11 F9 60.9(2) . . . . ?
C6 C7 C11 F9 -55.1(2) . . . . ?
C8 C7 C11 F9 -179.67(15) . . . . ?
O1 C7 C11 C12 -59.4(2) . . . . ?
C6 C7 C11 C12 -175.39(17) . . . . ?
C8 C7 C11 C12 60.0(2) . . . . ?
F8 C11 C12 F10 165.77(19) . . . . ?
F9 C11 C12 F10 -80.7(2) . . . . ?
C7 C11 C12 F10 39.4(3) . . . . ?
F8 C11 C12 F11 46.4(2) . . . . ?
F9 C11 C12 F11 159.99(17) . . . . ?
C7 C11 C12 F11 -80.0(2) . . . . ?
F8 C11 C12 C13 -71.9(3) . . . . ?
F9 C11 C12 C13 41.7(3) . . . . ?
C7 C11 C12 C13 161.7(2) . . . . ?
F10 C12 C13 F14 -67.0(3) . . . . ?
F11 C12 C13 F14 48.7(3) . . . . ?
C11 C12 C13 F14 168.5(3) . . . . ?
F10 C12 C13 F12 168.4(2) . . . . ?
F11 C12 C13 F12 -75.8(3) . . . . ?
C11 C12 C13 F12 43.9(3) . . . . ?
F10 C12 C13 F13 50.1(3) . . . . ?
F11 C12 C13 F13 165.9(2) . . . . ?
C11 C12 C13 F13 -74.4(3) . . . . ?
C6 C1 P1 O1 3.69(15) . . . . ?
C2 C1 P1 O1 -177.82(19) . . . . ?
C6 C1 P1 O1 178.68(15) . . . 2_756 ?
C2 C1 P1 O1 -2.82(19) . . . 2_756 ?
C6 C1 P1 C14 -87.94(15) . . . . ?
C2 C1 P1 C14 90.55(19) . . . . ?
C6 C1 P1 C1 92.06(15) . . . 2_756 ?
C2 C1 P1 C1 -89.45(19) . . . 2_756 ?
C6 C7 O1 P1 7.2(2) . . . . ?
C8 C7 O1 P1 129.66(14) . . . . ?
C11 C7 O1 P1 -109.17(15) . . . . ?
O1 P1 O1 C7 -70.80(13) 2_756 . . . ?
C14 P1 O1 C7 109.21(13) . . . . ?
C1 P1 O1 C7 -6.55(15) . . . . ?
C1 P1 O1 C7 -134.87(14) 2_756 . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        27.88
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         1.081
_refine_diff_density_min         -0.807
_refine_diff_density_rms         0.213