# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_coden_Cambridge 182 _publ_requested_journal 'Chemical Communications' loop_ _publ_author_name 'OHagan, David' 'Bresciani, Stefano' 'Lebl, Tomas' 'Slawin, Alexandra' _publ_contact_author_name 'David OHagan' _publ_contact_author_address ; Purdie Building North Haugh St Andrews Fife United Kingdom ; _publ_contact_author_email do1@st-andrews.ac.uk # Attachment '- 8.cif' data_8 _database_code_depnum_ccdc_archive 'CCDC 775192' #TrackingRef '- 8.cif' # start Validation Reply Form _vrf_PLAT029_8 ; PROBLEM: _diffrn_measured_fraction_theta_full Low ....... 0.85 RESPONSE: Very small weakly diffracting crystal - best of 3 attempts presented. ; _vrf_PLAT213_8 ; PROBLEM: Atom C2 has ADP max/min Ratio ..... 7.00 prola RESPONSE: No disorder - correct atom assigment and genuine value. ; _vrf_PLAT222_8 ; PROBLEM: Large Non-Solvent H Ueq(max)/Ueq(min) ... 7.50 Ratio RESPONSE: Very small weakly diffracting crystal - best of 3 attempts presented. ; # end Validation Reply Form _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_absolute_configuration syn _chemical_formula_moiety 'C6 H9 F3 O3' _chemical_formula_sum 'C6 H9 F3 O3' _chemical_formula_weight 186.13 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 5.507(3) _cell_length_b 7.525(4) _cell_length_c 18.773(9) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 777.9(7) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 2479 _cell_measurement_theta_min 4.68 _cell_measurement_theta_max 48.27 _exptl_crystal_description colourless _exptl_crystal_colour needle _exptl_crystal_size_max 0.100 _exptl_crystal_size_mid 0.100 _exptl_crystal_size_min 0.010 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.589 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 384 _exptl_absorpt_coefficient_mu 1.518 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8871 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator confocal _diffrn_measurement_device_type CCD _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4650 _diffrn_reflns_av_R_equivalents 0.1393 _diffrn_reflns_av_sigmaI/netI 0.0805 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 6.34 _diffrn_reflns_theta_max 66.27 _reflns_number_total 1101 _reflns_number_gt 814 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Corp., 2004)' _computing_cell_refinement 'CrystalClear (Rigaku Corp., 2004)' _computing_data_reduction 'CrystalClear (Rigaku Corp., 2004)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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. The OH hydrogen atoms were located from a difference map and refined isotropically subject to a distance constraint. ; _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^)+(0.1398P)^2^+5.3934P] 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 -1.1(16) _refine_ls_number_reflns 1101 _refine_ls_number_parameters 118 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.1892 _refine_ls_R_factor_gt 0.1567 _refine_ls_wR_factor_ref 0.3752 _refine_ls_wR_factor_gt 0.3500 _refine_ls_goodness_of_fit_ref 1.152 _refine_ls_restrained_S_all 1.151 _refine_ls_shift/su_max 0.025 _refine_ls_shift/su_mean 0.007 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 O1 O 0.7986(17) 0.0121(12) 0.3382(5) 0.061(3) Uani 1 1 d . . . C1 C 0.675(3) -0.1397(17) 0.3125(9) 0.071(5) Uani 1 1 d . . . H1A H 0.5624 -0.1031 0.2735 0.086 Uiso 1 1 calc R . . O2 O 0.836(2) -0.2561(15) 0.2866(6) 0.079(3) Uani 1 1 d D . . H2O H 0.87(4) -0.383(8) 0.283(13) 0.15(9) Uiso 1 1 d D . . C2 C 0.528(2) -0.215(2) 0.3739(8) 0.074(5) Uani 1 1 d . . . H2A H 0.6431 -0.2606 0.4108 0.089 Uiso 1 1 calc R . . F2 F 0.3919(15) -0.3618(14) 0.3468(6) 0.089(3) Uani 1 1 d . . . C3 C 0.365(2) -0.081(2) 0.4079(9) 0.069(5) Uani 1 1 d . . . H3A H 0.2327 -0.0451 0.3742 0.083 Uiso 1 1 calc R . . F3 F 0.2662(18) -0.1546(14) 0.4695(6) 0.097(3) Uani 1 1 d . . . C4 C 0.525(2) 0.080(2) 0.4265(8) 0.060(4) Uani 1 1 d . . . H4A H 0.6451 0.0519 0.4649 0.072 Uiso 1 1 calc R . . F4 F 0.3499(16) 0.2109(14) 0.4488(5) 0.091(3) Uani 1 1 d . . . C5 C 0.645(3) 0.1474(18) 0.3607(8) 0.057(4) Uani 1 1 d . . . H5A H 0.5210 0.1734 0.3233 0.069 Uiso 1 1 calc R . . C6 C 0.796(3) 0.3104(19) 0.3754(8) 0.066(4) Uani 1 1 d . . . H6A H 0.6963 0.3994 0.4009 0.079 Uiso 1 1 calc R . . H6B H 0.9348 0.2782 0.4063 0.079 Uiso 1 1 calc R . . O6 O 0.883(2) 0.3848(18) 0.3112(7) 0.098(4) Uani 1 1 d D . . H6O H 1.032(10) 0.352(13) 0.286(4) 0.02(3) Uiso 1 1 d 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 O1 0.047(5) 0.062(6) 0.074(6) 0.004(5) 0.017(5) -0.003(5) C1 0.081(11) 0.032(7) 0.101(12) -0.002(8) 0.002(10) 0.015(8) O2 0.073(8) 0.060(7) 0.104(8) -0.014(6) 0.023(7) 0.001(7) C2 0.028(7) 0.118(14) 0.076(10) 0.049(10) -0.040(7) -0.012(8) F2 0.044(4) 0.103(7) 0.119(8) 0.003(6) 0.005(5) 0.000(5) C3 0.021(6) 0.092(11) 0.094(12) -0.003(9) -0.007(7) 0.043(8) F3 0.076(7) 0.116(8) 0.099(7) 0.004(6) 0.031(6) 0.002(7) C4 0.030(6) 0.089(11) 0.060(9) 0.010(8) -0.001(7) 0.036(8) F4 0.059(6) 0.116(8) 0.098(7) -0.019(6) -0.002(5) 0.013(6) C5 0.056(8) 0.052(8) 0.064(9) -0.007(7) 0.019(7) 0.046(7) C6 0.073(10) 0.054(9) 0.070(10) -0.021(7) -0.008(8) -0.014(8) O6 0.081(8) 0.112(10) 0.100(9) -0.003(8) 0.049(7) 0.010(8) _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 O1 C5 1.389(14) . ? O1 C1 1.414(17) . ? C1 O2 1.338(18) . ? C1 C2 1.52(2) . ? C1 H1A 1.0000 . ? O2 H2O 0.98(2) . ? C2 F2 1.428(18) . ? C2 C3 1.50(2) . ? C2 H2A 1.0000 . ? C3 F3 1.393(19) . ? C3 C4 1.54(2) . ? C3 H3A 1.0000 . ? C4 F4 1.442(16) . ? C4 C5 1.49(2) . ? C4 H4A 1.0000 . ? C5 C6 1.51(2) . ? C5 H5A 1.0000 . ? C6 O6 1.413(19) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? O6 H6O 0.98(2) . ? 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 C5 O1 C1 113.8(11) . . ? O2 C1 O1 109.6(13) . . ? O2 C1 C2 112.6(13) . . ? O1 C1 C2 107.4(13) . . ? O2 C1 H1A 109.0 . . ? O1 C1 H1A 109.0 . . ? C2 C1 H1A 109.0 . . ? C1 O2 H2O 144(10) . . ? F2 C2 C3 111.0(11) . . ? F2 C2 C1 107.4(13) . . ? C3 C2 C1 113.1(14) . . ? F2 C2 H2A 108.4 . . ? C3 C2 H2A 108.4 . . ? C1 C2 H2A 108.4 . . ? F3 C3 C2 108.7(13) . . ? F3 C3 C4 110.3(13) . . ? C2 C3 C4 106.4(11) . . ? F3 C3 H3A 110.5 . . ? C2 C3 H3A 110.5 . . ? C4 C3 H3A 110.5 . . ? F4 C4 C5 107.7(11) . . ? F4 C4 C3 102.6(9) . . ? C5 C4 C3 109.5(13) . . ? F4 C4 H4A 112.2 . . ? C5 C4 H4A 112.2 . . ? C3 C4 H4A 112.2 . . ? O1 C5 C4 105.8(11) . . ? O1 C5 C6 108.5(11) . . ? C4 C5 C6 111.7(12) . . ? O1 C5 H5A 110.3 . . ? C4 C5 H5A 110.3 . . ? C6 C5 H5A 110.2 . . ? O6 C6 C5 110.8(12) . . ? O6 C6 H6A 109.5 . . ? C5 C6 H6A 109.5 . . ? O6 C6 H6B 109.5 . . ? C5 C6 H6B 109.5 . . ? H6A C6 H6B 108.1 . . ? C6 O6 H6O 127(6) . . ? 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 C5 O1 C1 O2 174.8(12) . . . . ? C5 O1 C1 C2 -62.5(15) . . . . ? O2 C1 C2 F2 -62.8(15) . . . . ? O1 C1 C2 F2 176.4(11) . . . . ? O2 C1 C2 C3 174.4(13) . . . . ? O1 C1 C2 C3 53.6(15) . . . . ? F2 C2 C3 F3 68.1(16) . . . . ? C1 C2 C3 F3 -171.1(12) . . . . ? F2 C2 C3 C4 -173.1(11) . . . . ? C1 C2 C3 C4 -52.3(15) . . . . ? F3 C3 C4 F4 -70.5(13) . . . . ? C2 C3 C4 F4 171.8(11) . . . . ? F3 C3 C4 C5 175.3(9) . . . . ? C2 C3 C4 C5 57.6(14) . . . . ? C1 O1 C5 C4 69.1(15) . . . . ? C1 O1 C5 C6 -170.9(11) . . . . ? F4 C4 C5 O1 -175.7(11) . . . . ? C3 C4 C5 O1 -64.8(13) . . . . ? F4 C4 C5 C6 66.5(14) . . . . ? C3 C4 C5 C6 177.4(11) . . . . ? O1 C5 C6 O6 71.0(16) . . . . ? C4 C5 C6 O6 -172.7(12) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O2 H2O O6 0.98(2) 1.83(10) 2.753(17) 156(21) 1_545 O6 H6O O2 0.98(2) 1.74(6) 2.623(16) 148(8) 3_755 _diffrn_measured_fraction_theta_max 0.854 _diffrn_reflns_theta_full 66.27 _diffrn_measured_fraction_theta_full 0.854 _refine_diff_density_max 0.438 _refine_diff_density_min -0.369 _refine_diff_density_rms 0.103 # Attachment '- 9.cif' data_9 _database_code_depnum_ccdc_archive 'CCDC 775193' #TrackingRef '- 9.cif' # start Validation Reply Form _vrf_PLAT415_9 ; PROBLEM: Short Inter D-H..H-X H3A .. H16O .. 1.52 Ang. RESPONSE: short contact. ; _vrf_PLAT417_9 ; PROBLEM: Short Inter D-H..H-D H6O .. H16O .. 1.60 Ang. RESPONSE:short contact. ; # end Validation Reply Form _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_absolute_configuration rmad _chemical_formula_moiety 'C6 H9 F3 O3' _chemical_formula_sum 'C6 H9 F3 O3' _chemical_formula_weight 186.13 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' _cell_length_a 6.373(5) _cell_length_b 6.623(9) _cell_length_c 10.220(8) _cell_angle_alpha 88.89(7) _cell_angle_beta 72.96(6) _cell_angle_gamma 75.90(5) _cell_volume 399.4(7) _cell_formula_units_Z 2 _cell_measurement_temperature 93(2) _cell_measurement_reflns_used 1291 _cell_measurement_theta_min 3.2 _cell_measurement_theta_max 27.7 _exptl_crystal_description Prism _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.548 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 192 _exptl_absorpt_coefficient_mu 0.164 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.930 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' _exptl_special_details ; ? ; _diffrn_ambient_temperature 93(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator confocal _diffrn_measurement_device_type CCD _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3843 _diffrn_reflns_av_R_equivalents 0.0235 _diffrn_reflns_av_sigmaI/netI 0.0235 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 3.18 _diffrn_reflns_theta_max 25.33 _reflns_number_total 2297 _reflns_number_gt 2287 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Corp., 2004)' _computing_cell_refinement 'CrystalClear (Rigaku Corp., 2004)' _computing_data_reduction 'CrystalClear (Rigaku Corp., 2004)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0662P)^2^+0.0780P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.3(6) _refine_ls_number_reflns 2297 _refine_ls_number_parameters 217 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0345 _refine_ls_R_factor_gt 0.0345 _refine_ls_wR_factor_ref 0.0983 _refine_ls_wR_factor_gt 0.0982 _refine_ls_goodness_of_fit_ref 1.157 _refine_ls_restrained_S_all 1.156 _refine_ls_shift/su_max 0.019 _refine_ls_shift/su_mean 0.003 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_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 O1 O 0.7555(3) 0.9203(2) 0.04172(17) 0.0160(3) Uani 1 1 d . . . C1 C 0.6034(4) 1.1128(3) 0.0292(2) 0.0163(5) Uani 1 1 d . . . H1A H 0.5306 1.1867 0.1218 0.020 Uiso 1 1 calc R . . O2 O 0.7328(3) 1.2335(2) -0.05596(18) 0.0190(4) Uani 1 1 d . . . H2O H 0.8012 1.3040 -0.0022 0.029 Uiso 1 1 calc R . . C2 C 0.4196(4) 1.0740(3) -0.0271(2) 0.0182(5) Uani 1 1 d . . . H2A H 0.3076 1.2088 -0.0278 0.022 Uiso 1 1 calc R . . F2 F 0.5211(2) 0.9848(2) -0.16098(14) 0.0209(3) Uani 1 1 d . . . C3 C 0.2991(4) 0.9219(3) 0.0570(2) 0.0171(5) Uani 1 1 d . . . H3A H 0.1914 0.8846 0.0131 0.021 Uiso 1 1 calc R . . F3 F 0.1824(2) 1.02234(19) 0.18702(14) 0.0211(3) Uani 1 1 d . . . C4 C 0.4727(4) 0.7293(3) 0.0723(2) 0.0163(5) Uani 1 1 d . . . H4A H 0.5546 0.6569 -0.0200 0.020 Uiso 1 1 calc R . . F4 F 0.3609(2) 0.59534(19) 0.15686(14) 0.0219(3) Uani 1 1 d . . . C5 C 0.6440(4) 0.7856(3) 0.1329(2) 0.0157(5) Uani 1 1 d . . . H5A H 0.5628 0.8611 0.2243 0.019 Uiso 1 1 calc R . . C6 C 0.8263(4) 0.5980(3) 0.1481(2) 0.0176(5) Uani 1 1 d . . . H6A H 0.9270 0.6450 0.1919 0.021 Uiso 1 1 calc R . . H6B H 0.7538 0.5004 0.2090 0.021 Uiso 1 1 calc R . . O6 O 0.9588(3) 0.4911(2) 0.01916(17) 0.0188(4) Uani 1 1 d . . . H6O H 1.0663 0.5702 -0.0303 0.028 Uiso 1 1 calc R . . O11 O 1.1888(3) 0.2845(2) -0.28562(16) 0.0175(4) Uani 1 1 d . . . C11 C 1.1766(4) 0.1231(3) -0.3717(2) 0.0186(5) Uani 1 1 d . . . H11A H 1.3271 0.0199 -0.4037 0.022 Uiso 1 1 calc R . . O12 O 1.0137(3) 0.0254(2) -0.29520(18) 0.0208(4) Uani 1 1 d . . . H12O H 1.0881 -0.1015 -0.2594 0.031 Uiso 1 1 calc R . . C12 C 1.1036(4) 0.2127(4) -0.4946(3) 0.0220(5) Uani 1 1 d . . . H12A H 1.1096 0.0977 -0.5586 0.026 Uiso 1 1 calc R . . F12 F 0.8851(3) 0.3395(2) -0.44802(17) 0.0305(4) Uani 1 1 d . . . C13 C 1.2532(5) 0.3536(4) -0.5697(3) 0.0221(5) Uani 1 1 d . . . H13A H 1.1888 0.4304 -0.6400 0.027 Uiso 1 1 calc R . . F13 F 1.4683(3) 0.2232(2) -0.63291(15) 0.0278(4) Uani 1 1 d . . . C14 C 1.2740(4) 0.5051(3) -0.4691(2) 0.0180(5) Uani 1 1 d . . . H14A H 1.1220 0.6021 -0.4267 0.022 Uiso 1 1 calc R . . F14 F 1.4260(3) 0.6215(2) -0.53864(15) 0.0273(4) Uani 1 1 d . . . C15 C 1.3580(4) 0.3902(3) -0.3564(2) 0.0173(5) Uani 1 1 d . . . H15A H 1.5045 0.2853 -0.3985 0.021 Uiso 1 1 calc R . . C16 C 1.3892(4) 0.5345(4) -0.2541(3) 0.0198(5) Uani 1 1 d . . . H16A H 1.4428 0.4506 -0.1837 0.024 Uiso 1 1 calc R . . H16B H 1.5074 0.6060 -0.3022 0.024 Uiso 1 1 calc R . . O16 O 1.1868(3) 0.6865(2) -0.18862(18) 0.0226(4) Uani 1 1 d . . . H16O H 1.1976 0.7398 -0.1027 0.034 Uiso 1 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 O1 0.0142(8) 0.0154(7) 0.0186(8) 0.0030(6) -0.0034(7) -0.0058(6) C1 0.0175(12) 0.0124(9) 0.0173(11) 0.0008(8) -0.0016(10) -0.0048(8) O2 0.0215(9) 0.0161(7) 0.0191(8) 0.0015(6) -0.0017(7) -0.0093(6) C2 0.0187(13) 0.0166(10) 0.0163(12) 0.0022(9) -0.0022(10) -0.0029(9) F2 0.0224(8) 0.0261(7) 0.0138(7) 0.0024(5) -0.0040(6) -0.0068(5) C3 0.0166(12) 0.0193(10) 0.0143(12) -0.0001(9) -0.0022(9) -0.0052(9) F3 0.0175(7) 0.0238(6) 0.0172(7) -0.0009(5) 0.0000(6) -0.0027(5) C4 0.0164(12) 0.0180(10) 0.0138(12) 0.0029(8) -0.0021(9) -0.0063(9) F4 0.0200(8) 0.0220(7) 0.0272(8) 0.0104(6) -0.0076(6) -0.0117(6) C5 0.0175(12) 0.0149(10) 0.0135(12) 0.0015(8) -0.0022(9) -0.0047(9) C6 0.0183(12) 0.0195(10) 0.0159(12) 0.0046(9) -0.0059(10) -0.0057(9) O6 0.0170(9) 0.0186(7) 0.0179(9) 0.0000(6) -0.0007(7) -0.0044(6) O11 0.0206(9) 0.0176(7) 0.0140(8) 0.0015(6) -0.0029(7) -0.0070(6) C11 0.0198(13) 0.0169(10) 0.0169(12) -0.0016(8) -0.0007(10) -0.0057(9) O12 0.0220(10) 0.0205(8) 0.0193(9) 0.0011(6) -0.0015(7) -0.0098(7) C12 0.0211(14) 0.0288(12) 0.0182(13) -0.0011(9) -0.0044(11) -0.0118(10) F12 0.0194(8) 0.0415(8) 0.0348(9) 0.0097(7) -0.0120(7) -0.0107(6) C13 0.0236(14) 0.0294(12) 0.0133(12) 0.0047(9) -0.0021(10) -0.0107(10) F13 0.0264(9) 0.0349(8) 0.0177(8) -0.0058(6) 0.0038(7) -0.0115(6) C14 0.0181(12) 0.0189(10) 0.0163(12) 0.0037(9) -0.0016(10) -0.0078(9) F14 0.0339(9) 0.0305(7) 0.0213(8) 0.0091(6) -0.0045(7) -0.0198(7) C15 0.0164(12) 0.0164(10) 0.0168(12) 0.0004(8) -0.0010(10) -0.0048(9) C16 0.0214(13) 0.0215(10) 0.0169(12) 0.0028(8) -0.0050(10) -0.0072(9) O16 0.0297(10) 0.0170(7) 0.0176(8) -0.0019(6) -0.0003(7) -0.0074(7) _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 O1 C1 1.430(3) . ? O1 C5 1.434(3) . ? C1 O2 1.397(3) . ? C1 C2 1.522(4) . ? C1 H1A 1.0000 . ? O2 H2O 0.9800 . ? C2 F2 1.402(3) . ? C2 C3 1.516(3) . ? C2 H2A 1.0000 . ? C3 F3 1.405(3) . ? C3 C4 1.510(3) . ? C3 H3A 1.0000 . ? C4 F4 1.400(3) . ? C4 C5 1.522(3) . ? C4 H4A 1.0000 . ? C5 C6 1.521(3) . ? C5 H5A 1.0000 . ? C6 O6 1.430(3) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? O6 H6O 0.9800 . ? O11 C11 1.428(3) . ? O11 C15 1.438(3) . ? C11 O12 1.393(3) . ? C11 C12 1.525(4) . ? C11 H11A 1.0000 . ? O12 H12O 0.9800 . ? C12 F12 1.389(3) . ? C12 C13 1.531(3) . ? C12 H12A 1.0000 . ? C13 F13 1.403(3) . ? C13 C14 1.506(4) . ? C13 H13A 1.0000 . ? C14 F14 1.406(3) . ? C14 C15 1.523(3) . ? C14 H14A 1.0000 . ? C15 C16 1.517(4) . ? C15 H15A 1.0000 . ? C16 O16 1.419(3) . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? O16 H16O 0.9800 . ? 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 C1 O1 C5 112.63(19) . . ? O2 C1 O1 107.2(2) . . ? O2 C1 C2 112.0(2) . . ? O1 C1 C2 110.79(18) . . ? O2 C1 H1A 108.9 . . ? O1 C1 H1A 108.9 . . ? C2 C1 H1A 108.9 . . ? C1 O2 H2O 109.5 . . ? F2 C2 C3 107.44(18) . . ? F2 C2 C1 108.7(2) . . ? C3 C2 C1 111.40(19) . . ? F2 C2 H2A 109.8 . . ? C3 C2 H2A 109.8 . . ? C1 C2 H2A 109.8 . . ? F3 C3 C4 108.88(19) . . ? F3 C3 C2 106.32(19) . . ? C4 C3 C2 109.2(2) . . ? F3 C3 H3A 110.8 . . ? C4 C3 H3A 110.8 . . ? C2 C3 H3A 110.8 . . ? F4 C4 C3 108.9(2) . . ? F4 C4 C5 110.11(17) . . ? C3 C4 C5 111.09(19) . . ? F4 C4 H4A 108.9 . . ? C3 C4 H4A 108.9 . . ? C5 C4 H4A 108.9 . . ? O1 C5 C6 107.3(2) . . ? O1 C5 C4 107.86(17) . . ? C6 C5 C4 113.51(19) . . ? O1 C5 H5A 109.4 . . ? C6 C5 H5A 109.4 . . ? C4 C5 H5A 109.4 . . ? O6 C6 C5 112.13(19) . . ? O6 C6 H6A 109.2 . . ? C5 C6 H6A 109.2 . . ? O6 C6 H6B 109.2 . . ? C5 C6 H6B 109.2 . . ? H6A C6 H6B 107.9 . . ? C6 O6 H6O 109.5 . . ? C11 O11 C15 111.37(18) . . ? O12 C11 O11 107.94(19) . . ? O12 C11 C12 108.1(2) . . ? O11 C11 C12 110.99(19) . . ? O12 C11 H11A 109.9 . . ? O11 C11 H11A 109.9 . . ? C12 C11 H11A 109.9 . . ? C11 O12 H12O 109.5 . . ? F12 C12 C11 108.9(2) . . ? F12 C12 C13 106.1(2) . . ? C11 C12 C13 110.8(2) . . ? F12 C12 H12A 110.3 . . ? C11 C12 H12A 110.3 . . ? C13 C12 H12A 110.3 . . ? F13 C13 C14 108.9(2) . . ? F13 C13 C12 106.8(2) . . ? C14 C13 C12 110.2(2) . . ? F13 C13 H13A 110.3 . . ? C14 C13 H13A 110.3 . . ? C12 C13 H13A 110.3 . . ? F14 C14 C13 109.25(19) . . ? F14 C14 C15 109.72(19) . . ? C13 C14 C15 110.7(2) . . ? F14 C14 H14A 109.0 . . ? C13 C14 H14A 109.0 . . ? C15 C14 H14A 109.0 . . ? O11 C15 C16 108.8(2) . . ? O11 C15 C14 106.5(2) . . ? C16 C15 C14 113.11(19) . . ? O11 C15 H15A 109.5 . . ? C16 C15 H15A 109.5 . . ? C14 C15 H15A 109.5 . . ? O16 C16 C15 112.7(2) . . ? O16 C16 H16A 109.1 . . ? C15 C16 H16A 109.1 . . ? O16 C16 H16B 109.1 . . ? C15 C16 H16B 109.1 . . ? H16A C16 H16B 107.8 . . ? C16 O16 H16O 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 C5 O1 C1 O2 177.09(16) . . . . ? C5 O1 C1 C2 -60.4(2) . . . . ? O2 C1 C2 F2 55.0(2) . . . . ? O1 C1 C2 F2 -64.7(2) . . . . ? O2 C1 C2 C3 173.17(17) . . . . ? O1 C1 C2 C3 53.5(3) . . . . ? F2 C2 C3 F3 -174.87(18) . . . . ? C1 C2 C3 F3 66.2(2) . . . . ? F2 C2 C3 C4 67.8(2) . . . . ? C1 C2 C3 C4 -51.2(2) . . . . ? F3 C3 C4 F4 60.8(2) . . . . ? C2 C3 C4 F4 176.47(18) . . . . ? F3 C3 C4 C5 -60.7(2) . . . . ? C2 C3 C4 C5 55.1(2) . . . . ? C1 O1 C5 C6 -174.44(18) . . . . ? C1 O1 C5 C4 62.9(2) . . . . ? F4 C4 C5 O1 179.22(16) . . . . ? C3 C4 C5 O1 -60.1(2) . . . . ? F4 C4 C5 C6 60.5(2) . . . . ? C3 C4 C5 C6 -178.86(19) . . . . ? O1 C5 C6 O6 -57.6(2) . . . . ? C4 C5 C6 O6 61.5(3) . . . . ? C15 O11 C11 O12 178.61(17) . . . . ? C15 O11 C11 C12 -63.1(3) . . . . ? O12 C11 C12 F12 54.2(2) . . . . ? O11 C11 C12 F12 -64.0(3) . . . . ? O12 C11 C12 C13 170.44(18) . . . . ? O11 C11 C12 C13 52.3(3) . . . . ? F12 C12 C13 F13 -172.33(18) . . . . ? C11 C12 C13 F13 69.7(3) . . . . ? F12 C12 C13 C14 69.6(3) . . . . ? C11 C12 C13 C14 -48.5(3) . . . . ? F13 C13 C14 F14 58.5(2) . . . . ? C12 C13 C14 F14 175.37(19) . . . . ? F13 C13 C14 C15 -62.4(2) . . . . ? C12 C13 C14 C15 54.4(3) . . . . ? C11 O11 C15 C16 -170.98(18) . . . . ? C11 O11 C15 C14 66.8(2) . . . . ? F14 C14 C15 O11 176.98(18) . . . . ? C13 C14 C15 O11 -62.4(2) . . . . ? F14 C14 C15 C16 57.6(2) . . . . ? C13 C14 C15 C16 178.2(2) . . . . ? O11 C15 C16 O16 -59.7(2) . . . . ? C14 C15 C16 O16 58.4(3) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O2 H2O O6 0.98 1.83 2.734(3) 152.5 1_565 O6 H6O O16 0.98 1.82 2.701(3) 147.9 . O12 H12O O16 0.98 1.64 2.616(4) 174.1 1_545 O16 H16O O1 0.98 2.74 3.125(4) 103.7 . O16 H16O O6 0.98 2.57 2.701(3) 86.9 . _diffrn_measured_fraction_theta_max 0.975 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.980 _refine_diff_density_max 0.347 _refine_diff_density_min -0.349 _refine_diff_density_rms 0.052