# Supplementary Material (ESI) for Chemical Communications
# This journal is © The Royal Society of Chemistry 2002

data_ca9801 
_database_code_CSD                  184932

_journal_coden_Cambridge      182

_publ_requested_journal       'Chemical Communications'

loop_
_publ_author_name
'Abell, Chris'
'Coggins, J.'
'Frederickson, Martyn'

_publ_contact_author_name     	'Dr Chris Abell'  
_publ_contact_author_address 
;
University Chemical Laboratory
Lensfield Road
Cambridge
CB2 1EW
UNITED KINGDOM
;

_publ_contact_author_email       'CA26@CAM.AC.UK'

_publ_section_title		
;
Vinyl fluoride as an isoelectronic replacement for an enolate anion
in the inhibition of type II dehydroquinases
;

_audit_creation_method            SHELXL 
_chemical_name_systematic 
; 
? 
; 
_chemical_name_common             ? 
_chemical_formula_moiety          ? 
_chemical_formula_structural      ? 
_chemical_formula_analytical      ? 
_chemical_formula_sum             'C16 H26 F2 O8' 
_chemical_formula_weight          384.37 
_chemical_melting_point           ? 
_chemical_compound_source         ? 

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' 
'F'  'F'   0.0171   0.0103 
'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' 
'H'  'H'   0.0000   0.0000 
'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 

_symmetry_cell_setting            Tetragonal
_symmetry_space_group_name_H-M    P4(1)2(1)2 

loop_ 
_symmetry_equiv_pos_as_xyz 
'x, y, z' 
'-x, -y, z+1/2' 
'-y+1/2, x+1/2, z+1/4' 
'y+1/2, -x+1/2, z+3/4' 
'y, x, -z' 
'-y, -x, -z+1/2' 
'-x+1/2, y+1/2, -z+1/4' 
'x+1/2, -y+1/2, -z+3/4' 

_cell_length_a                    19.184(3) 
_cell_length_b                    19.184(3) 
_cell_length_c                    10.165(4) 
_cell_angle_alpha                 90.00 
_cell_angle_beta                  90.00 
_cell_angle_gamma                 90.00 
_cell_volume                      3740.9(17) 
_cell_formula_units_Z             8 
_cell_measurement_temperature     180(2) 
_cell_measurement_reflns_used     25 
_cell_measurement_theta_min       20 
_cell_measurement_theta_max       30 

_exptl_crystal_description        block 
_exptl_crystal_colour             white 
_exptl_crystal_size_max           0.20 
_exptl_crystal_size_mid           0.17 
_exptl_crystal_size_min           0.15 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_diffrn     1.365 
_exptl_crystal_density_method     ? 
_exptl_crystal_F_000              1632 
_exptl_absorpt_coefficient_mu     0.120 
_exptl_absorpt_correction_type    'Psi-scans' 
_exptl_absorpt_correction_T_min   0.982 
_exptl_absorpt_correction_T_max   1.000 

_exptl_special_details 
; 
? 
; 

_diffrn_ambient_temperature       180(2) 
_diffrn_radiation_wavelength      0.71069 
_diffrn_radiation_type            MoK\a 
_diffrn_radiation_source          'rotating anode' 
_diffrn_radiation_monochromator   graphite 
_diffrn_measurement_device        'Rigaku AFC7r' 
_diffrn_measurement_method        \w/2\q 
_diffrn_standards_number          3 
_diffrn_standards_interval_count  200 
_diffrn_standards_interval_time   ? 
_diffrn_standards_decay_%         1.4 
_diffrn_reflns_number             3845 
_diffrn_reflns_av_R_equivalents   0.0281 
_diffrn_reflns_av_sigmaI/netI     0.0666 
_diffrn_reflns_limit_h_min        -22 
_diffrn_reflns_limit_h_max        22 
_diffrn_reflns_limit_k_min        -16 
_diffrn_reflns_limit_k_max        16 
_diffrn_reflns_limit_l_min        -12 
_diffrn_reflns_limit_l_max        12 
_diffrn_reflns_theta_min          2.50 
_diffrn_reflns_theta_max          24.99 
_reflns_number_total              3296 
_reflns_number_observed           2455 
_reflns_observed_criterion        >2sigma(I) 

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

_refine_special_details 
; 
Refinement on F^2^ for ALL reflections except for 0 with very negative F^2^ 
or flagged by the user for potential systematic errors.  Weighted R-factors 
wR and all goodnesses of fit S are based on F^2^, conventional R-factors R 
are based on F, with F set to zero for negative F^2^. The observed criterion 
of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs etc. and is 
not relevant to the choice of reflections for refinement.  R-factors based 
on F^2^ are statistically about twice as large as those based on F, and R- 
factors based on ALL data will be even larger. 
; 

_refine_ls_structure_factor_coef  Fsqd  
_refine_ls_matrix_type            full 
_refine_ls_weighting_scheme 
'calc w=1/[\s^2^(Fo^2^)+(0.0419P)^2^+0.0000P] 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_abs_structure_details 
'Flack H D (1983), Acta Cryst. A39, 876-881' 
_refine_ls_abs_structure_Flack    1.10(120) 
_refine_ls_number_reflns          3296 
_refine_ls_number_parameters      241 
_refine_ls_number_restraints      0 
_refine_ls_R_factor_all           0.0738 
_refine_ls_R_factor_obs           0.0473 
_refine_ls_wR_factor_all          0.1077 
_refine_ls_wR_factor_obs          0.0960 
_refine_ls_goodness_of_fit_all    1.024 
_refine_ls_goodness_of_fit_obs    1.070 
_refine_ls_restrained_S_all       1.024 
_refine_ls_restrained_S_obs       1.070 
_refine_ls_shift/esd_max          -0.013 
_refine_ls_shift/esd_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_thermal_displace_type 
_atom_site_occupancy 
_atom_site_calc_flag 
_atom_site_refinement_flags 
_atom_site_disorder_group 
F1 F 0.63281(9) 0.13123(9) 0.4385(2) 0.0357(4) Uani 1 d . . 
F3 F 0.55653(9) 0.05202(9) 0.3883(2) 0.0411(5) Uani 1 d . . 
O1 O 0.57001(10) 0.16199(10) 0.2072(2) 0.0290(5) Uani 1 d . . 
O2 O 0.68333(10) 0.15080(10) 0.0353(2) 0.0294(5) Uani 1 d . . 
O3 O 0.53716(11) 0.14099(11) -0.0103(2) 0.0358(5) Uani 1 d . . 
O4 O 0.66003(10) 0.26530(10) 0.1008(2) 0.0321(5) Uani 1 d . . 
O5 O 0.77789(12) -0.07783(11) 0.3648(2) 0.0425(6) Uani 1 d . . 
O6 O 0.85544(11) -0.00998(11) 0.2613(2) 0.0433(6) Uani 1 d . . 
O7 O 0.77788(11) 0.09804(11) 0.3861(2) 0.0343(5) Uani 1 d . . 
O8 O 0.84650(12) 0.04574(12) 0.5497(2) 0.0477(7) Uani 1 d . . 
C1 C 0.6206(2) 0.0775(2) 0.3514(3) 0.0306(7) Uani 1 d . . 
C2 C 0.61695(15) 0.10500(15) 0.2125(3) 0.0268(7) Uani 1 d . . 
H2 H 0.59974(15) 0.06719(15) 0.1531(3) 0.032 Uiso 1 calc R . 
C3 C 0.5642(2) 0.1909(2) 0.0778(3) 0.0290(7) Uani 1 d . . 
C4 C 0.6375(2) 0.2089(2) 0.0219(3) 0.0301(7) Uani 1 d . . 
C5 C 0.68853(15) 0.12719(15) 0.1685(3) 0.0254(7) Uani 1 d . . 
H5 H 0.70541(15) 0.16617(15) 0.2255(3) 0.030 Uiso 1 calc R . 
C6 C 0.7396(2) 0.0673(2) 0.1746(3) 0.0305(7) Uani 1 d . . 
H6A H 0.7856(2) 0.0828(2) 0.1417(3) 0.037 Uiso 1 calc R . 
H6B H 0.7231(2) 0.0288(2) 0.1177(3) 0.037 Uiso 1 calc R . 
C7 C 0.7467(2) 0.04150(15) 0.3161(3) 0.0291(7) Uani 1 d . . 
C8 C 0.6745(2) 0.0211(2) 0.3686(3) 0.0317(7) Uani 1 d . . 
H8A H 0.6585(2) -0.0214(2) 0.3224(3) 0.038 Uiso 1 calc R . 
H8B H 0.6785(2) 0.0098(2) 0.4633(3) 0.038 Uiso 1 calc R . 
C9 C 0.5181(2) 0.2540(2) 0.0931(3) 0.0355(8) Uani 1 d . . 
H9A H 0.5382(6) 0.2855(5) 0.1590(14) 0.043 Uiso 1 calc R . 
H9B H 0.4716(3) 0.2393(2) 0.1215(18) 0.043 Uiso 1 calc R . 
H9C H 0.5145(8) 0.2784(6) 0.0086(6) 0.043 Uiso 1 calc R . 
C10 C 0.6369(2) 0.2261(2) -0.1242(3) 0.0376(8) Uani 1 d . . 
H10A H 0.6101(8) 0.2689(6) -0.1388(4) 0.045 Uiso 1 calc R . 
H10B H 0.6153(9) 0.1877(5) -0.1729(4) 0.045 Uiso 1 calc R . 
H10C H 0.6848(2) 0.2328(9) -0.1551(5) 0.045 Uiso 1 calc R . 
C11 C 0.4710(2) 0.1118(2) 0.0233(4) 0.0487(10) Uani 1 d . . 
H11A H 0.4612(5) 0.0721(7) -0.0343(15) 0.058 Uiso 1 calc R . 
H11B H 0.4347(2) 0.1472(4) 0.0122(20) 0.058 Uiso 1 calc R . 
H11C H 0.4718(4) 0.0962(10) 0.1150(7) 0.058 Uiso 1 calc R . 
C12 C 0.7300(2) 0.2884(2) 0.0772(4) 0.0436(9) Uani 1 d . . 
H12A H 0.7414(4) 0.3264(8) 0.1380(14) 0.052 Uiso 1 calc R . 
H12B H 0.7340(3) 0.3051(10) -0.0136(7) 0.052 Uiso 1 calc R . 
H12C H 0.7623(2) 0.2496(3) 0.0910(20) 0.052 Uiso 1 calc R . 
C13 C 0.7940(2) -0.0228(2) 0.3194(3) 0.0324(8) Uani 1 d . . 
C14 C 0.9035(2) -0.0678(2) 0.2633(5) 0.0597(12) Uani 1 d . . 
H14A H 0.9488(4) -0.0526(4) 0.2296(22) 0.072 Uiso 1 calc R . 
H14B H 0.8854(6) -0.1055(5) 0.2080(18) 0.072 Uiso 1 calc R . 
H14C H 0.9088(9) -0.0846(8) 0.3538(5) 0.072 Uiso 1 calc R . 
C15 C 0.7898(2) 0.0887(2) 0.5217(3) 0.0489(10) Uani 1 d . . 
H15A H 0.7978(2) 0.1349(2) 0.5626(3) 0.059 Uiso 1 calc R . 
H15B H 0.7475(2) 0.0684(2) 0.5622(3) 0.059 Uiso 1 calc R . 
C16 C 0.9115(2) 0.0773(2) 0.5184(5) 0.0650(12) Uani 1 d . . 
H16A H 0.9496(2) 0.0468(7) 0.5467(23) 0.078 Uiso 1 calc R . 
H16B H 0.9152(6) 0.1222(7) 0.5638(20) 0.078 Uiso 1 calc R . 
H16C H 0.9144(6) 0.0847(12) 0.4232(5) 0.078 Uiso 1 calc R . 

loop_ 
_atom_site_aniso_label 
_atom_site_aniso_U_11 
_atom_site_aniso_U_22 
_atom_site_aniso_U_33 
_atom_site_aniso_U_23 
_atom_site_aniso_U_13 
_atom_site_aniso_U_12 
F1 0.0446(11) 0.0330(10) 0.0294(10) -0.0026(9) 0.0036(8) 0.0040(8) 
F3 0.0329(10) 0.0405(11) 0.0499(12) 0.0120(9) 0.0121(9) 0.0000(9) 
O1 0.0314(12) 0.0265(11) 0.0291(12) 0.0030(9) 0.0024(10) 0.0027(9) 
O2 0.0325(12) 0.0318(12) 0.0240(11) 0.0057(9) 0.0007(9) 0.0014(10) 
O3 0.0338(13) 0.0373(13) 0.0363(13) -0.0037(10) -0.0035(10) -0.0088(10) 
O4 0.0311(12) 0.0284(12) 0.0368(13) 0.0043(10) -0.0051(10) -0.0100(10) 
O5 0.0515(15) 0.0307(13) 0.0453(15) 0.0119(12) 0.0149(13) 0.0087(11) 
O6 0.0365(13) 0.0328(13) 0.061(2) 0.0100(12) 0.0123(12) 0.0076(11) 
O7 0.0386(13) 0.0314(12) 0.0328(13) 0.0000(10) -0.0088(11) 0.0024(10) 
O8 0.0442(14) 0.0487(15) 0.050(2) 0.0166(13) -0.0139(13) -0.0062(12) 
C1 0.029(2) 0.025(2) 0.038(2) 0.0000(15) 0.0101(15) -0.0036(14) 
C2 0.033(2) 0.022(2) 0.026(2) 0.0011(13) 0.0004(14) 0.0013(13) 
C3 0.030(2) 0.027(2) 0.030(2) 0.0020(14) -0.0093(14) -0.0013(13) 
C4 0.032(2) 0.026(2) 0.032(2) 0.0007(14) -0.0041(14) -0.0022(14) 
C5 0.028(2) 0.025(2) 0.023(2) 0.0038(13) -0.0006(13) -0.0001(13) 
C6 0.029(2) 0.032(2) 0.030(2) 0.0052(14) 0.0050(14) 0.0000(14) 
C7 0.033(2) 0.027(2) 0.028(2) 0.0007(14) 0.0016(14) 0.0019(14) 
C8 0.035(2) 0.031(2) 0.029(2) 0.0037(15) 0.0032(15) 0.0010(14) 
C9 0.036(2) 0.033(2) 0.037(2) 0.0044(15) -0.005(2) 0.0003(15) 
C10 0.040(2) 0.040(2) 0.032(2) 0.009(2) -0.003(2) 0.000(2) 
C11 0.039(2) 0.047(2) 0.060(3) -0.004(2) -0.005(2) -0.016(2) 
C12 0.034(2) 0.039(2) 0.058(2) 0.014(2) -0.011(2) -0.013(2) 
C13 0.037(2) 0.034(2) 0.026(2) 0.003(2) 0.0016(15) 0.005(2) 
C14 0.046(2) 0.049(2) 0.084(3) 0.005(2) 0.013(2) 0.018(2) 
C15 0.047(2) 0.062(3) 0.037(2) -0.004(2) -0.009(2) 0.005(2) 
C16 0.048(2) 0.062(3) 0.086(3) 0.014(3) -0.018(2) -0.009(2) 

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

loop_ 
_geom_bond_atom_site_label_1 
_geom_bond_atom_site_label_2 
_geom_bond_distance 
_geom_bond_site_symmetry_2 
_geom_bond_publ_flag 
F1 C1 1.380(3) . ? 
F3 C1 1.374(3) . ? 
O1 C2 1.417(3) . ? 
O1 C3 1.431(4) . ? 
O2 C4 1.426(4) . ? 
O2 C5 1.430(3) . ? 
O3 C3 1.410(3) . ? 
O3 C11 1.428(4) . ? 
O4 C4 1.414(3) . ? 
O4 C12 1.433(3) . ? 
O5 C13 1.193(4) . ? 
O6 C13 1.342(4) . ? 
O6 C14 1.442(4) . ? 
O7 C15 1.409(4) . ? 
O7 C7 1.429(4) . ? 
O8 C15 1.393(4) . ? 
O8 C16 1.422(4) . ? 
C1 C8 1.507(4) . ? 
C1 C2 1.508(4) . ? 
C2 C5 1.506(4) . ? 
C2 H2 1.00 . ? 
C3 C9 1.508(4) . ? 
C3 C4 1.556(4) . ? 
C4 C10 1.522(4) . ? 
C5 C6 1.511(4) . ? 
C5 H5 1.00 . ? 
C6 C7 1.527(4) . ? 
C6 H6A 0.99 . ? 
C6 H6B 0.99 . ? 
C7 C13 1.532(4) . ? 
C7 C8 1.535(4) . ? 
C8 H8A 0.99 . ? 
C8 H8B 0.99 . ? 
C9 H9A 0.98 . ? 
C9 H9B 0.98 . ? 
C9 H9C 0.98 . ? 
C10 H10A 0.98 . ? 
C10 H10B 0.98 . ? 
C10 H10C 0.98 . ? 
C11 H11A 0.98 . ? 
C11 H11B 0.98 . ? 
C11 H11C 0.98 . ? 
C12 H12A 0.98 . ? 
C12 H12B 0.98 . ? 
C12 H12C 0.98 . ? 
C14 H14A 0.98 . ? 
C14 H14B 0.98 . ? 
C14 H14C 0.98 . ? 
C15 H15A 0.99 . ? 
C15 H15B 0.99 . ? 
C16 H16A 0.98 . ? 
C16 H16B 0.98 . ? 
C16 H16C 0.98 . ? 

loop_ 
_geom_angle_atom_site_label_1 
_geom_angle_atom_site_label_2 
_geom_angle_atom_site_label_3 
_geom_angle 
_geom_angle_site_symmetry_1 
_geom_angle_site_symmetry_3 
_geom_angle_publ_flag 
C2 O1 C3 112.6(2) . . ? 
C4 O2 C5 112.4(2) . . ? 
C3 O3 C11 116.2(3) . . ? 
C4 O4 C12 115.3(3) . . ? 
C13 O6 C14 114.4(3) . . ? 
C15 O7 C7 117.3(3) . . ? 
C15 O8 C16 112.7(3) . . ? 
F3 C1 F1 104.0(2) . . ? 
F3 C1 C8 109.1(2) . . ? 
F1 C1 C8 110.2(3) . . ? 
F3 C1 C2 109.8(2) . . ? 
F1 C1 C2 110.3(2) . . ? 
C8 C1 C2 113.1(3) . . ? 
O1 C2 C5 110.5(2) . . ? 
O1 C2 C1 109.6(2) . . ? 
C5 C2 C1 109.6(2) . . ? 
O1 C2 H2 109.06(14) . . ? 
C5 C2 H2 109.1(2) . . ? 
C1 C2 H2 109.1(2) . . ? 
O3 C3 O1 110.4(2) . . ? 
O3 C3 C9 113.2(2) . . ? 
O1 C3 C9 105.2(3) . . ? 
O3 C3 C4 104.6(2) . . ? 
O1 C3 C4 110.6(2) . . ? 
C9 C3 C4 112.9(3) . . ? 
O4 C4 O2 110.9(2) . . ? 
O4 C4 C10 112.9(2) . . ? 
O2 C4 C10 105.5(2) . . ? 
O4 C4 C3 103.8(2) . . ? 
O2 C4 C3 110.4(2) . . ? 
C10 C4 C3 113.4(3) . . ? 
O2 C5 C2 107.9(2) . . ? 
O2 C5 C6 109.0(2) . . ? 
C2 C5 C6 111.3(2) . . ? 
O2 C5 H5 109.53(15) . . ? 
C2 C5 H5 109.5(2) . . ? 
C6 C5 H5 109.5(2) . . ? 
C5 C6 C7 110.1(2) . . ? 
C5 C6 H6A 109.6(2) . . ? 
C7 C6 H6A 109.6(2) . . ? 
C5 C6 H6B 109.6(2) . . ? 
C7 C6 H6B 109.6(2) . . ? 
H6A C6 H6B 108.2 . . ? 
O7 C7 C6 105.1(2) . . ? 
O7 C7 C13 110.6(2) . . ? 
C6 C7 C13 109.6(2) . . ? 
O7 C7 C8 113.5(3) . . ? 
C6 C7 C8 109.3(3) . . ? 
C13 C7 C8 108.8(2) . . ? 
C1 C8 C7 113.3(2) . . ? 
C1 C8 H8A 108.9(2) . . ? 
C7 C8 H8A 108.9(2) . . ? 
C1 C8 H8B 108.9(2) . . ? 
C7 C8 H8B 108.9(2) . . ? 
H8A C8 H8B 107.7 . . ? 
C3 C9 H9A 109.5(2) . . ? 
C3 C9 H9B 109.5(2) . . ? 
H9A C9 H9B 109.5 . . ? 
C3 C9 H9C 109.5(2) . . ? 
H9A C9 H9C 109.5 . . ? 
H9B C9 H9C 109.5 . . ? 
C4 C10 H10A 109.5(2) . . ? 
C4 C10 H10B 109.5(2) . . ? 
H10A C10 H10B 109.5 . . ? 
C4 C10 H10C 109.5(2) . . ? 
H10A C10 H10C 109.5 . . ? 
H10B C10 H10C 109.5 . . ? 
O3 C11 H11A 109.5(2) . . ? 
O3 C11 H11B 109.5(2) . . ? 
H11A C11 H11B 109.5 . . ? 
O3 C11 H11C 109.5(2) . . ? 
H11A C11 H11C 109.5 . . ? 
H11B C11 H11C 109.5 . . ? 
O4 C12 H12A 109.5(2) . . ? 
O4 C12 H12B 109.5(2) . . ? 
H12A C12 H12B 109.5 . . ? 
O4 C12 H12C 109.5(2) . . ? 
H12A C12 H12C 109.5 . . ? 
H12B C12 H12C 109.5 . . ? 
O5 C13 O6 124.1(3) . . ? 
O5 C13 C7 124.6(3) . . ? 
O6 C13 C7 111.3(3) . . ? 
O6 C14 H14A 109.5(2) . . ? 
O6 C14 H14B 109.5(2) . . ? 
H14A C14 H14B 109.5 . . ? 
O6 C14 H14C 109.5(2) . . ? 
H14A C14 H14C 109.5 . . ? 
H14B C14 H14C 109.5 . . ? 
O8 C15 O7 113.7(3) . . ? 
O8 C15 H15A 108.8(2) . . ? 
O7 C15 H15A 108.8(2) . . ? 
O8 C15 H15B 108.8(2) . . ? 
O7 C15 H15B 108.8(2) . . ? 
H15A C15 H15B 107.7 . . ? 
O8 C16 H16A 109.5(2) . . ? 
O8 C16 H16B 109.5(2) . . ? 
H16A C16 H16B 109.5 . . ? 
O8 C16 H16C 109.5(2) . . ? 
H16A C16 H16C 109.5 . . ? 
H16B C16 H16C 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 
C3 O1 C2 C5 58.9(3) . . . . ? 
C3 O1 C2 C1 179.8(2) . . . . ? 
F3 C1 C2 O1 63.4(3) . . . . ? 
F1 C1 C2 O1 -50.7(3) . . . . ? 
C8 C1 C2 O1 -174.5(2) . . . . ? 
F3 C1 C2 C5 -175.2(2) . . . . ? 
F1 C1 C2 C5 70.7(3) . . . . ? 
C8 C1 C2 C5 -53.2(3) . . . . ? 
C11 O3 C3 O1 57.2(3) . . . . ? 
C11 O3 C3 C9 -60.5(4) . . . . ? 
C11 O3 C3 C4 176.1(2) . . . . ? 
C2 O1 C3 O3 62.5(3) . . . . ? 
C2 O1 C3 C9 -175.0(2) . . . . ? 
C2 O1 C3 C4 -52.7(3) . . . . ? 
C12 O4 C4 O2 56.1(3) . . . . ? 
C12 O4 C4 C10 -62.1(3) . . . . ? 
C12 O4 C4 C3 174.7(2) . . . . ? 
C5 O2 C4 O4 58.5(3) . . . . ? 
C5 O2 C4 C10 -178.8(2) . . . . ? 
C5 O2 C4 C3 -55.9(3) . . . . ? 
O3 C3 C4 O4 172.6(2) . . . . ? 
O1 C3 C4 O4 -68.6(3) . . . . ? 
C9 C3 C4 O4 49.0(3) . . . . ? 
O3 C3 C4 O2 -68.6(3) . . . . ? 
O1 C3 C4 O2 50.2(3) . . . . ? 
C9 C3 C4 O2 167.9(2) . . . . ? 
O3 C3 C4 C10 49.6(3) . . . . ? 
O1 C3 C4 C10 168.4(2) . . . . ? 
C9 C3 C4 C10 -73.9(3) . . . . ? 
C4 O2 C5 C2 60.8(3) . . . . ? 
C4 O2 C5 C6 -178.2(2) . . . . ? 
O1 C2 C5 O2 -61.0(3) . . . . ? 
C1 C2 C5 O2 178.2(2) . . . . ? 
O1 C2 C5 C6 179.5(2) . . . . ? 
C1 C2 C5 C6 58.6(3) . . . . ? 
O2 C5 C6 C7 179.5(2) . . . . ? 
C2 C5 C6 C7 -61.6(3) . . . . ? 
C15 O7 C7 C6 179.2(3) . . . . ? 
C15 O7 C7 C13 -62.6(3) . . . . ? 
C15 O7 C7 C8 59.9(3) . . . . ? 
C5 C6 C7 O7 -65.6(3) . . . . ? 
C5 C6 C7 C13 175.5(3) . . . . ? 
C5 C6 C7 C8 56.4(3) . . . . ? 
F3 C1 C8 C7 173.8(2) . . . . ? 
F1 C1 C8 C7 -72.6(3) . . . . ? 
C2 C1 C8 C7 51.3(4) . . . . ? 
O7 C7 C8 C1 64.9(4) . . . . ? 
C6 C7 C8 C1 -52.0(3) . . . . ? 
C13 C7 C8 C1 -171.5(3) . . . . ? 
C14 O6 C13 O5 -3.1(5) . . . . ? 
C14 O6 C13 C7 178.6(3) . . . . ? 
O7 C7 C13 O5 120.2(3) . . . . ? 
C6 C7 C13 O5 -124.4(3) . . . . ? 
C8 C7 C13 O5 -5.0(4) . . . . ? 
O7 C7 C13 O6 -61.5(3) . . . . ? 
C6 C7 C13 O6 53.9(3) . . . . ? 
C8 C7 C13 O6 173.2(3) . . . . ? 
C16 O8 C15 O7 70.3(4) . . . . ? 
C7 O7 C15 O8 75.4(4) . . . . ? 

_refine_diff_density_max    0.158 
_refine_diff_density_min   -0.170 
_refine_diff_density_rms    0.039