# Electronic Supplementary Material (ESI) for Organic and Biomolecular Chemistry
# This journal is © The Royal Society of Chemistry 2011


data_global
_journal_name_full               Org.Biomol.Chem.
_journal_coden_cambridge         0177
_journal_year                    ?
_journal_volume                  ?
_journal_page_first              ?
loop_
_publ_author_name
'Tong Wang'
'Song Ye'
_publ_contact_author_name        'Song Ye'
_publ_contact_author_email       songye@iccas.ac.cn

data_sa829
_database_code_depnum_ccdc_archive 'CCDC 817788'
#TrackingRef 'sa829.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H19 F3 O3'
_chemical_formula_sum            'C18 H19 F3 O3'
_chemical_formula_weight         340.33

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P2(1)/n

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

_cell_length_a                   5.935(3)
_cell_length_b                   23.843(10)
_cell_length_c                   11.898(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.864(5)
_cell_angle_gamma                90.00
_cell_volume                     1679.8(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    517
_cell_measurement_theta_min      2.17
_cell_measurement_theta_max      27.48

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.43
_exptl_crystal_size_min          0.23
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.346
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             712
_exptl_absorpt_coefficient_mu    0.112
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.9461
_exptl_absorpt_correction_T_max  0.9747
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      294(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Saturn724+ CCD'
_diffrn_measurement_method       '\w scans at fixed \c = 45\%'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11224
_diffrn_reflns_av_R_equivalents  0.0359
_diffrn_reflns_av_sigmaI/netI    0.0267
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.08
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2939
_reflns_number_gt                2702
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'XP in Siemens SHELXTL (Sheldrick, 1994)'
_computing_publication_material  'SHELX97 (Sheldrick, 1997)'

_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^)+(0.0585P)^2^+0.7943P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2939
_refine_ls_number_parameters     272
_refine_ls_number_restraints     127
_refine_ls_R_factor_all          0.0887
_refine_ls_R_factor_gt           0.0811
_refine_ls_wR_factor_ref         0.1821
_refine_ls_wR_factor_gt          0.1772
_refine_ls_goodness_of_fit_ref   1.246
_refine_ls_restrained_S_all      1.237
_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
F1 F 0.6612(4) -0.06015(10) 0.05209(16) 0.0969(7) Uani 1 1 d . . .
F2 F 0.8482(4) -0.12465(9) 0.14312(19) 0.0980(7) Uani 1 1 d . . .
F3 F 0.5207(3) -0.10089(9) 0.19224(17) 0.0826(6) Uani 1 1 d . . .
O1 O 0.6595(3) 0.00858(8) 0.23328(16) 0.0581(5) Uani 1 1 d . A .
O2 O 0.4237(4) 0.10769(10) 0.2040(2) 0.0779(7) Uani 1 1 d . . .
O3 O 0.7142(4) 0.14408(10) 0.1152(2) 0.0879(8) Uani 1 1 d D . .
C1 C 0.8232(5) -0.03657(12) 0.2344(2) 0.0548(7) Uani 1 1 d . . .
C2 C 1.0372(5) -0.01167(14) 0.1827(3) 0.0660(8) Uani 1 1 d . . .
H2A H 1.1646 -0.0099 0.2381 0.079 Uiso 1 1 calc R . .
H2B H 1.0791 -0.0334 0.1184 0.079 Uiso 1 1 calc R . .
C3 C 0.9578(5) 0.04518(14) 0.1484(3) 0.0631(8) Uani 1 1 d . A .
H3A H 1.0417 0.0711 0.1103 0.076 Uiso 1 1 calc R . .
C4 C 0.7520(5) 0.05381(12) 0.1793(2) 0.0546(7) Uani 1 1 d . . .
C5 C 0.6083(5) 0.10398(13) 0.1704(3) 0.0619(8) Uani 1 1 d . A .
C6 C 0.5965(15) 0.1976(3) 0.0817(8) 0.074(2) Uani 0.647(10) 1 d PDU A 1
H6A H 0.4391 0.1908 0.0550 0.088 Uiso 0.647(10) 1 calc PR A 1
C7 C 0.6113(14) 0.2301(4) 0.1922(7) 0.083(2) Uani 0.647(10) 1 d PDU A 1
H7A H 0.5119 0.2624 0.1846 0.100 Uiso 0.647(10) 1 calc PR A 1
H7B H 0.5584 0.2064 0.2512 0.100 Uiso 0.647(10) 1 calc PR A 1
C8 C 0.8443(18) 0.2497(3) 0.2265(7) 0.084(2) Uani 0.647(10) 1 d PDU A 1
H8A H 0.9345 0.2176 0.2518 0.100 Uiso 0.647(10) 1 calc PR A 1
H8B H 0.8373 0.2751 0.2898 0.100 Uiso 0.647(10) 1 calc PR A 1
C9 C 0.9603(14) 0.2789(3) 0.1345(8) 0.089(2) Uani 0.647(10) 1 d PDU A 1
H9A H 1.1156 0.2867 0.1603 0.107 Uiso 0.647(10) 1 calc PR A 1
H9B H 0.8858 0.3145 0.1177 0.107 Uiso 0.647(10) 1 calc PR A 1
C10 C 0.9568(15) 0.2439(4) 0.0282(8) 0.092(2) Uani 0.647(10) 1 d PDU A 1
H10A H 1.0147 0.2662 -0.0317 0.110 Uiso 0.647(10) 1 calc PR A 1
H10B H 1.0561 0.2119 0.0412 0.110 Uiso 0.647(10) 1 calc PR A 1
C11 C 0.726(2) 0.2236(4) -0.0084(6) 0.084(2) Uani 0.647(10) 1 d PDU A 1
H11A H 0.7396 0.1962 -0.0680 0.100 Uiso 0.647(10) 1 calc PR A 1
H11B H 0.6399 0.2550 -0.0404 0.100 Uiso 0.647(10) 1 calc PR A 1
C6' C 0.604(2) 0.2026(5) 0.1314(13) 0.063(4) Uani 0.353(10) 1 d PDU A 2
H6'A H 0.4478 0.1978 0.1521 0.076 Uiso 0.353(10) 1 calc PR A 2
C7' C 0.730(4) 0.2407(8) 0.2161(15) 0.095(5) Uani 0.353(10) 1 d PDU A 2
H7'A H 0.6530 0.2765 0.2180 0.114 Uiso 0.353(10) 1 calc PR A 2
H7'B H 0.7293 0.2240 0.2904 0.114 Uiso 0.353(10) 1 calc PR A 2
C8' C 0.969(3) 0.2502(8) 0.1882(15) 0.102(5) Uani 0.353(10) 1 d PDU A 2
H8'A H 1.0517 0.2151 0.1940 0.123 Uiso 0.353(10) 1 calc PR A 2
H8'B H 1.0409 0.2766 0.2412 0.123 Uiso 0.353(10) 1 calc PR A 2
C9' C 0.973(3) 0.2729(8) 0.0708(17) 0.104(5) Uani 0.353(10) 1 d PDU A 2
H9'A H 1.1281 0.2762 0.0509 0.125 Uiso 0.353(10) 1 calc PR A 2
H9'B H 0.9063 0.3101 0.0679 0.125 Uiso 0.353(10) 1 calc PR A 2
C10' C 0.845(3) 0.2356(8) -0.0131(15) 0.097(5) Uani 0.353(10) 1 d PDU A 2
H10C H 0.8468 0.2525 -0.0872 0.116 Uiso 0.353(10) 1 calc PR A 2
H10D H 0.9222 0.1998 -0.0156 0.116 Uiso 0.353(10) 1 calc PR A 2
C11' C 0.604(3) 0.2252(7) 0.0122(13) 0.081(4) Uani 0.353(10) 1 d PDU A 2
H11C H 0.5350 0.1983 -0.0407 0.097 Uiso 0.353(10) 1 calc PR A 2
H11D H 0.5183 0.2599 0.0056 0.097 Uiso 0.353(10) 1 calc PR A 2
C12 C 0.8618(5) -0.06025(11) 0.3523(2) 0.0547(7) Uani 1 1 d . . .
C13 C 0.7026(5) -0.05202(13) 0.4306(3) 0.0639(8) Uani 1 1 d . . .
H13A H 0.5731 -0.0313 0.4109 0.077 Uiso 1 1 calc R . .
C14 C 0.7342(7) -0.07430(15) 0.5378(3) 0.0785(10) Uani 1 1 d . . .
H14A H 0.6263 -0.0683 0.5897 0.094 Uiso 1 1 calc R . .
C15 C 0.9229(7) -0.10511(15) 0.5681(3) 0.0822(11) Uani 1 1 d . . .
H15A H 0.9433 -0.1202 0.6402 0.099 Uiso 1 1 calc R . .
C16 C 1.0824(7) -0.11357(16) 0.4910(4) 0.0853(11) Uani 1 1 d . . .
H16A H 1.2113 -0.1344 0.5113 0.102 Uiso 1 1 calc R . .
C17 C 1.0528(6) -0.09140(14) 0.3838(3) 0.0724(9) Uani 1 1 d . . .
H17A H 1.1617 -0.0974 0.3325 0.087 Uiso 1 1 calc R . .
C18 C 0.7123(5) -0.08085(15) 0.1555(3) 0.0685(9) 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
F1 0.1097(17) 0.1222(18) 0.0582(12) -0.0077(11) 0.0016(11) -0.0237(14)
F2 0.1019(16) 0.0871(15) 0.1069(17) -0.0398(13) 0.0210(13) 0.0036(12)
F3 0.0742(12) 0.0902(14) 0.0841(13) -0.0130(11) 0.0116(10) -0.0275(10)
O1 0.0492(11) 0.0633(12) 0.0633(12) 0.0068(10) 0.0142(9) -0.0005(9)
O2 0.0571(14) 0.0792(16) 0.0988(18) 0.0088(13) 0.0156(12) -0.0027(11)
O3 0.0715(15) 0.0701(14) 0.123(2) 0.0226(14) 0.0161(14) -0.0045(12)
C1 0.0492(15) 0.0628(17) 0.0538(16) -0.0042(13) 0.0133(12) -0.0002(13)
C2 0.0492(17) 0.083(2) 0.0678(19) -0.0044(17) 0.0164(14) -0.0047(15)
C3 0.0538(17) 0.075(2) 0.0617(18) 0.0026(15) 0.0106(13) -0.0144(15)
C4 0.0501(16) 0.0628(17) 0.0511(15) 0.0033(13) 0.0038(12) -0.0130(13)
C5 0.0553(18) 0.0650(19) 0.0648(19) 0.0084(15) 0.0006(14) -0.0118(15)
C6 0.068(3) 0.078(4) 0.073(5) -0.005(4) -0.008(4) -0.001(3)
C7 0.080(5) 0.084(4) 0.087(5) 0.000(4) 0.013(4) -0.002(4)
C8 0.091(6) 0.080(4) 0.078(4) -0.010(3) -0.009(4) -0.010(4)
C9 0.089(4) 0.081(4) 0.095(5) 0.000(4) 0.001(4) -0.027(3)
C10 0.087(5) 0.097(5) 0.093(5) 0.002(4) 0.021(4) -0.019(4)
C11 0.103(7) 0.077(4) 0.070(4) 0.014(3) -0.007(5) -0.009(5)
C6' 0.062(5) 0.063(6) 0.065(7) 0.016(6) 0.007(6) 0.001(5)
C7' 0.096(9) 0.107(8) 0.084(8) -0.007(6) 0.019(8) 0.006(8)
C8' 0.095(8) 0.102(8) 0.107(8) -0.001(7) -0.014(7) -0.010(7)
C9' 0.100(7) 0.099(8) 0.115(9) 0.001(8) 0.022(8) -0.007(7)
C10' 0.093(9) 0.111(8) 0.087(7) 0.014(6) 0.012(7) -0.013(7)
C11' 0.082(7) 0.083(6) 0.076(7) 0.010(6) -0.007(6) -0.003(6)
C12 0.0538(16) 0.0488(15) 0.0622(17) -0.0076(13) 0.0080(13) -0.0026(13)
C13 0.0699(19) 0.0642(18) 0.0584(18) -0.0056(15) 0.0102(14) 0.0079(15)
C14 0.100(3) 0.079(2) 0.059(2) -0.0010(17) 0.0147(18) 0.009(2)
C15 0.108(3) 0.072(2) 0.064(2) 0.0006(17) -0.010(2) -0.001(2)
C16 0.080(2) 0.076(2) 0.097(3) 0.006(2) -0.019(2) 0.0125(19)
C17 0.0622(19) 0.075(2) 0.080(2) 0.0011(18) 0.0073(17) 0.0104(17)
C18 0.065(2) 0.077(2) 0.065(2) -0.0114(17) 0.0130(15) -0.0066(17)

_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
F1 C18 1.341(4) . ?
F2 C18 1.334(4) . ?
F3 C18 1.335(4) . ?
O1 C4 1.387(3) . ?
O1 C1 1.450(3) . ?
O2 C5 1.195(4) . ?
O3 C5 1.340(4) . ?
O3 C6 1.495(8) . ?
O3 C6' 1.560(12) . ?
C1 C12 1.514(4) . ?
C1 C18 1.532(4) . ?
C1 C2 1.565(4) . ?
C2 C3 1.483(5) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.315(4) . ?
C3 H3A 0.9300 . ?
C4 C5 1.469(4) . ?
C6 C11 1.497(10) . ?
C6 C7 1.524(9) . ?
C6 H6A 0.9800 . ?
C7 C8 1.490(9) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.503(10) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.514(9) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.488(9) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C6' C7' 1.517(14) . ?
C6' C11' 1.517(13) . ?
C6' H6'A 0.9800 . ?
C7' C8' 1.493(14) . ?
C7' H7'A 0.9700 . ?
C7' H7'B 0.9700 . ?
C8' C9' 1.500(14) . ?
C8' H8'A 0.9700 . ?
C8' H8'B 0.9700 . ?
C9' C10' 1.505(14) . ?
C9' H9'A 0.9700 . ?
C9' H9'B 0.9700 . ?
C10' C11' 1.501(13) . ?
C10' H10C 0.9700 . ?
C10' H10D 0.9700 . ?
C11' H11C 0.9700 . ?
C11' H11D 0.9700 . ?
C12 C17 1.385(4) . ?
C12 C13 1.386(4) . ?
C13 C14 1.382(4) . ?
C13 H13A 0.9300 . ?
C14 C15 1.367(5) . ?
C14 H14A 0.9300 . ?
C15 C16 1.377(5) . ?
C15 H15A 0.9300 . ?
C16 C17 1.381(5) . ?
C16 H16A 0.9300 . ?
C17 H17A 0.9300 . ?

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
C4 O1 C1 107.2(2) . . ?
C5 O3 C6 120.9(4) . . ?
C5 O3 C6' 111.3(6) . . ?
C6 O3 C6' 22.6(4) . . ?
O1 C1 C12 110.2(2) . . ?
O1 C1 C18 104.2(2) . . ?
C12 C1 C18 110.0(2) . . ?
O1 C1 C2 106.0(2) . . ?
C12 C1 C2 115.4(2) . . ?
C18 C1 C2 110.3(2) . . ?
C3 C2 C1 101.8(2) . . ?
C3 C2 H2A 111.4 . . ?
C1 C2 H2A 111.4 . . ?
C3 C2 H2B 111.4 . . ?
C1 C2 H2B 111.4 . . ?
H2A C2 H2B 109.3 . . ?
C4 C3 C2 110.5(3) . . ?
C4 C3 H3A 124.8 . . ?
C2 C3 H3A 124.8 . . ?
C3 C4 O1 114.3(3) . . ?
C3 C4 C5 130.8(3) . . ?
O1 C4 C5 114.9(2) . . ?
O2 C5 O3 125.6(3) . . ?
O2 C5 C4 125.3(3) . . ?
O3 C5 C4 109.1(3) . . ?
O3 C6 C11 106.9(6) . . ?
O3 C6 C7 101.9(6) . . ?
C11 C6 C7 113.8(7) . . ?
O3 C6 H6A 111.3 . . ?
C11 C6 H6A 111.3 . . ?
C7 C6 H6A 111.3 . . ?
C8 C7 C6 113.2(7) . . ?
C8 C7 H7A 108.9 . . ?
C6 C7 H7A 108.9 . . ?
C8 C7 H7B 108.9 . . ?
C6 C7 H7B 108.9 . . ?
H7A C7 H7B 107.7 . . ?
C7 C8 C9 114.1(7) . . ?
C7 C8 H8A 108.7 . . ?
C9 C8 H8A 108.7 . . ?
C7 C8 H8B 108.7 . . ?
C9 C8 H8B 108.7 . . ?
H8A C8 H8B 107.6 . . ?
C8 C9 C10 111.8(6) . . ?
C8 C9 H9A 109.3 . . ?
C10 C9 H9A 109.3 . . ?
C8 C9 H9B 109.3 . . ?
C10 C9 H9B 109.3 . . ?
H9A C9 H9B 107.9 . . ?
C11 C10 C9 112.6(7) . . ?
C11 C10 H10A 109.1 . . ?
C9 C10 H10A 109.1 . . ?
C11 C10 H10B 109.1 . . ?
C9 C10 H10B 109.1 . . ?
H10A C10 H10B 107.8 . . ?
C10 C11 C6 115.6(6) . . ?
C10 C11 H11A 108.4 . . ?
C6 C11 H11A 108.4 . . ?
C10 C11 H11B 108.4 . . ?
C6 C11 H11B 108.4 . . ?
H11A C11 H11B 107.4 . . ?
C7' C6' C11' 112.1(12) . . ?
C7' C6' O3 115.1(11) . . ?
C11' C6' O3 100.1(11) . . ?
C7' C6' H6'A 109.7 . . ?
C11' C6' H6'A 109.7 . . ?
O3 C6' H6'A 109.7 . . ?
C8' C7' C6' 112.2(13) . . ?
C8' C7' H7'A 109.2 . . ?
C6' C7' H7'A 109.2 . . ?
C8' C7' H7'B 109.2 . . ?
C6' C7' H7'B 109.2 . . ?
H7'A C7' H7'B 107.9 . . ?
C7' C8' C9' 109.7(14) . . ?
C7' C8' H8'A 109.7 . . ?
C9' C8' H8'A 109.7 . . ?
C7' C8' H8'B 109.7 . . ?
C9' C8' H8'B 109.7 . . ?
H8'A C8' H8'B 108.2 . . ?
C8' C9' C10' 111.4(14) . . ?
C8' C9' H9'A 109.3 . . ?
C10' C9' H9'A 109.3 . . ?
C8' C9' H9'B 109.3 . . ?
C10' C9' H9'B 109.3 . . ?
H9'A C9' H9'B 108.0 . . ?
C11' C10' C9' 114.2(14) . . ?
C11' C10' H10C 108.7 . . ?
C9' C10' H10C 108.7 . . ?
C11' C10' H10D 108.7 . . ?
C9' C10' H10D 108.7 . . ?
H10C C10' H10D 107.6 . . ?
C10' C11' C6' 107.9(13) . . ?
C10' C11' H11C 110.1 . . ?
C6' C11' H11C 110.1 . . ?
C10' C11' H11D 110.1 . . ?
C6' C11' H11D 110.1 . . ?
H11C C11' H11D 108.4 . . ?
C17 C12 C13 118.4(3) . . ?
C17 C12 C1 121.4(3) . . ?
C13 C12 C1 120.2(3) . . ?
C14 C13 C12 120.7(3) . . ?
C14 C13 H13A 119.7 . . ?
C12 C13 H13A 119.7 . . ?
C15 C14 C13 120.5(3) . . ?
C15 C14 H14A 119.7 . . ?
C13 C14 H14A 119.7 . . ?
C14 C15 C16 119.4(3) . . ?
C14 C15 H15A 120.3 . . ?
C16 C15 H15A 120.3 . . ?
C15 C16 C17 120.6(3) . . ?
C15 C16 H16A 119.7 . . ?
C17 C16 H16A 119.7 . . ?
C16 C17 C12 120.4(3) . . ?
C16 C17 H17A 119.8 . . ?
C12 C17 H17A 119.8 . . ?
F2 C18 F3 106.9(3) . . ?
F2 C18 F1 106.8(3) . . ?
F3 C18 F1 106.7(3) . . ?
F2 C18 C1 111.7(3) . . ?
F3 C18 C1 112.7(2) . . ?
F1 C18 C1 111.7(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C4 O1 C1 C12 130.0(2) . . . . ?
C4 O1 C1 C18 -112.0(2) . . . . ?
C4 O1 C1 C2 4.4(3) . . . . ?
O1 C1 C2 C3 -4.8(3) . . . . ?
C12 C1 C2 C3 -127.1(3) . . . . ?
C18 C1 C2 C3 107.4(3) . . . . ?
C1 C2 C3 C4 3.7(3) . . . . ?
C2 C3 C4 O1 -1.1(4) . . . . ?
C2 C3 C4 C5 176.0(3) . . . . ?
C1 O1 C4 C3 -2.3(3) . . . . ?
C1 O1 C4 C5 -179.9(2) . . . . ?
C6 O3 C5 O2 -5.1(6) . . . . ?
C6' O3 C5 O2 17.7(8) . . . . ?
C6 O3 C5 C4 172.7(5) . . . . ?
C6' O3 C5 C4 -164.4(7) . . . . ?
C3 C4 C5 O2 -178.1(3) . . . . ?
O1 C4 C5 O2 -1.0(4) . . . . ?
C3 C4 C5 O3 4.0(5) . . . . ?
O1 C4 C5 O3 -178.9(2) . . . . ?
C5 O3 C6 C11 -161.5(5) . . . . ?
C6' O3 C6 C11 128(2) . . . . ?
C5 O3 C6 C7 78.8(7) . . . . ?
C6' O3 C6 C7 8.4(17) . . . . ?
O3 C6 C7 C8 70.8(8) . . . . ?
C11 C6 C7 C8 -43.8(10) . . . . ?
C6 C7 C8 C9 49.0(10) . . . . ?
C7 C8 C9 C10 -52.8(11) . . . . ?
C8 C9 C10 C11 51.1(11) . . . . ?
C9 C10 C11 C6 -47.9(11) . . . . ?
O3 C6 C11 C10 -67.6(9) . . . . ?
C7 C6 C11 C10 44.1(11) . . . . ?
C5 O3 C6' C7' 102.0(12) . . . . ?
C6 O3 C6' C7' -138(3) . . . . ?
C5 O3 C6' C11' -137.6(9) . . . . ?
C6 O3 C6' C11' -17.8(15) . . . . ?
C11' C6' C7' C8' -57(2) . . . . ?
O3 C6' C7' C8' 56.4(19) . . . . ?
C6' C7' C8' C9' 56(2) . . . . ?
C7' C8' C9' C10' -54(2) . . . . ?
C8' C9' C10' C11' 56(2) . . . . ?
C9' C10' C11' C6' -55(2) . . . . ?
C7' C6' C11' C10' 54.2(18) . . . . ?
O3 C6' C11' C10' -68.3(14) . . . . ?
O1 C1 C12 C17 -160.8(3) . . . . ?
C18 C1 C12 C17 84.9(3) . . . . ?
C2 C1 C12 C17 -40.7(4) . . . . ?
O1 C1 C12 C13 20.6(4) . . . . ?
C18 C1 C12 C13 -93.8(3) . . . . ?
C2 C1 C12 C13 140.6(3) . . . . ?
C17 C12 C13 C14 0.2(5) . . . . ?
C1 C12 C13 C14 178.8(3) . . . . ?
C12 C13 C14 C15 -0.3(5) . . . . ?
C13 C14 C15 C16 0.3(6) . . . . ?
C14 C15 C16 C17 -0.2(6) . . . . ?
C15 C16 C17 C12 0.0(6) . . . . ?
C13 C12 C17 C16 0.0(5) . . . . ?
C1 C12 C17 C16 -178.7(3) . . . . ?
O1 C1 C18 F2 177.1(2) . . . . ?
C12 C1 C18 F2 -64.8(3) . . . . ?
C2 C1 C18 F2 63.7(3) . . . . ?
O1 C1 C18 F3 -62.6(3) . . . . ?
C12 C1 C18 F3 55.5(3) . . . . ?
C2 C1 C18 F3 -176.0(3) . . . . ?
O1 C1 C18 F1 57.6(3) . . . . ?
C12 C1 C18 F1 175.7(2) . . . . ?
C2 C1 C18 F1 -55.8(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.464
_refine_diff_density_min         -0.225
_refine_diff_density_rms         0.044