# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2003 data_global _publ_contact_author_email JMP29@LE.AC.UK _publ_contact_author_name 'Prof Jonathan Percy' _journal_name_full Org.Biomol.Chem. _journal_coden_Cambridge 0177 _publ_contact_author_address ; Chemistry University of Leicester University Road Leicester LE1 7RH UNITED KINGDOM ; _publ_section_title ; Syntheses of Selectively Fluorinated Cyclodecenones: the First Deployment of the Neutral oxy-Cope Rearrangement in Organofluorine Chemistry ; loop_ _publ_author_name 'Jonathan Percy' 'Gianluca DiMartino' 'Michael B. Hursthouse' 'Mark E. Light' 'Neil S. Spencer' ; M.Tolley ; data_14b _database_code_depnum_ccdc_archive 'CCDC 219860' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C13 H17 F3 O2' _chemical_formula_weight 262.27 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 P21/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 10.1391(5) _cell_length_b 8.2152(4) _cell_length_c 14.6853(5) _cell_angle_alpha 90.00 _cell_angle_beta 96.703(3) _cell_angle_gamma 90.00 _cell_volume 1214.85(9) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 9829 _cell_measurement_theta_min 3.20 _cell_measurement_theta_max 25.02 _exptl_crystal_description Block _exptl_crystal_colour Colourless _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 1.434 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 552 _exptl_absorpt_coefficient_mu 0.125 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.744 _exptl_absorpt_correction_T_max 0.977 _exptl_absorpt_process_details 'SORTAV (Blessing, 1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker Nonius FR591 Rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Nonius Kappa CCD Area detector' _diffrn_measurement_method '\f and \w scans to fill the asymmetric unit' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9829 _diffrn_reflns_av_R_equivalents 0.0605 _diffrn_reflns_av_sigmaI/netI 0.0405 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 3.20 _diffrn_reflns_theta_max 25.02 _reflns_number_total 2130 _reflns_number_gt 1701 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Hooft, 1998)' _computing_cell_refinement 'DENZO (Otwinowski and MInor, 1997)' _computing_data_reduction 'DENZO, COLLECT, MAXUS (Mackay et al., 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'CAMERON (Watkin, et al., 1993)' _computing_publication_material 'WINGX (Farrugia, 1998)' _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^)+(0.0443P)^2^+0.1870P] 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 SHELXL _refine_ls_extinction_coef 0.010(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2130 _refine_ls_number_parameters 232 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0503 _refine_ls_R_factor_gt 0.0352 _refine_ls_wR_factor_ref 0.0933 _refine_ls_wR_factor_gt 0.0858 _refine_ls_goodness_of_fit_ref 1.063 _refine_ls_restrained_S_all 1.063 _refine_ls_shift/su_max 0.111 _refine_ls_shift/su_mean 0.019 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 0.87436(14) -0.0512(2) 0.70130(10) 0.0262(4) Uani 1 1 d . . . C2 C 0.79193(14) 0.0619(2) 0.75493(10) 0.0254(4) Uani 1 1 d . . . C3 C 0.61989(17) 0.0731(2) 0.84813(11) 0.0324(4) Uani 1 1 d . . . C4 C 0.57531(16) 0.2401(2) 0.81435(11) 0.0325(4) Uani 1 1 d . . . C5 C 0.68833(17) 0.3314(2) 0.77760(12) 0.0319(4) Uani 1 1 d . . . C6 C 0.75902(15) 0.2285(2) 0.71058(10) 0.0267(4) Uani 1 1 d . . . C7 C 0.68235(14) 0.22007(19) 0.61499(10) 0.0267(4) Uani 1 1 d . . . C8 C 0.74741(14) 0.1215(2) 0.54768(10) 0.0266(4) Uani 1 1 d . . . C9 C 0.71133(15) -0.0228(2) 0.51567(10) 0.0268(4) Uani 1 1 d . . . C10 C 0.79037(18) -0.1341(2) 0.46259(11) 0.0329(4) Uani 1 1 d . . . C11 C 0.80906(18) -0.3010(2) 0.50877(12) 0.0331(4) Uani 1 1 d . . . C12 C 0.89152(17) -0.3052(2) 0.60284(11) 0.0310(4) Uani 1 1 d . . . C13 C 0.82942(16) -0.2234(2) 0.68122(11) 0.0284(4) Uani 1 1 d . . . O1 O 0.98116(10) -0.00087(15) 0.68330(7) 0.0344(3) Uani 1 1 d . . . O2 O 0.67704(9) -0.01810(13) 0.77860(7) 0.0281(3) Uani 1 1 d . . . F1 F 0.86234(9) 0.19248(12) 0.52942(6) 0.0375(3) Uani 1 1 d . . . F2 F 0.66532(10) 0.37706(12) 0.58226(6) 0.0415(3) Uani 1 1 d . . . F3 F 0.55670(8) 0.16122(11) 0.61718(6) 0.0326(3) Uani 1 1 d . . . H2 H 0.8511(14) 0.0848(19) 0.8110(11) 0.026(4) Uiso 1 1 d . . . H3A H 0.6897(16) 0.082(2) 0.9048(11) 0.034(4) Uiso 1 1 d . . . H3B H 0.5470(17) 0.006(2) 0.8655(11) 0.034(4) Uiso 1 1 d . . . H4A H 0.5445(15) 0.301(2) 0.8652(11) 0.031(4) Uiso 1 1 d . . . H4B H 0.5002(16) 0.228(2) 0.7661(11) 0.033(4) Uiso 1 1 d . . . H5A H 0.6573(16) 0.432(2) 0.7494(12) 0.037(5) Uiso 1 1 d . . . H5B H 0.7534(17) 0.357(2) 0.8266(12) 0.037(5) Uiso 1 1 d . . . H6 H 0.8417(17) 0.280(2) 0.7017(11) 0.035(4) Uiso 1 1 d . . . H9 H 0.6288(16) -0.066(2) 0.5334(11) 0.034(4) Uiso 1 1 d . . . H10A H 0.7437(17) -0.148(2) 0.4019(13) 0.042(5) Uiso 1 1 d . . . H10B H 0.8744(17) -0.083(2) 0.4549(11) 0.030(4) Uiso 1 1 d . . . H11A H 0.8498(17) -0.372(2) 0.4673(13) 0.042(5) Uiso 1 1 d . . . H11B H 0.7213(17) -0.3505(19) 0.5135(11) 0.029(4) Uiso 1 1 d . . . H12A H 0.9787(16) -0.256(2) 0.5973(11) 0.028(4) Uiso 1 1 d . . . H12B H 0.9089(15) -0.418(2) 0.6174(11) 0.033(4) Uiso 1 1 d . . . H13A H 0.8545(16) -0.284(2) 0.7375(12) 0.033(4) Uiso 1 1 d . . . H13B H 0.7312(16) -0.228(2) 0.6729(10) 0.028(4) Uiso 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 0.0192(8) 0.0349(10) 0.0231(8) 0.0037(7) -0.0030(6) 0.0014(7) C2 0.0177(7) 0.0336(10) 0.0243(8) -0.0005(7) -0.0002(6) -0.0035(6) C3 0.0295(9) 0.0430(11) 0.0258(9) 0.0009(8) 0.0082(7) -0.0002(8) C4 0.0270(9) 0.0437(11) 0.0271(8) -0.0052(8) 0.0049(7) 0.0045(8) C5 0.0326(9) 0.0319(10) 0.0308(9) -0.0047(8) 0.0018(7) 0.0005(8) C6 0.0211(8) 0.0289(9) 0.0304(8) -0.0016(7) 0.0041(6) -0.0051(7) C7 0.0251(8) 0.0253(9) 0.0304(9) 0.0058(7) 0.0056(6) -0.0005(6) C8 0.0220(8) 0.0323(10) 0.0260(8) 0.0064(7) 0.0044(6) -0.0024(7) C9 0.0227(8) 0.0334(10) 0.0239(8) 0.0057(7) 0.0006(6) 0.0015(7) C10 0.0348(10) 0.0364(10) 0.0280(9) -0.0002(8) 0.0057(7) -0.0009(8) C11 0.0346(10) 0.0299(10) 0.0350(9) -0.0053(8) 0.0050(7) -0.0004(8) C12 0.0271(9) 0.0279(10) 0.0383(10) 0.0003(8) 0.0047(7) 0.0026(7) C13 0.0253(9) 0.0298(10) 0.0298(9) 0.0056(7) 0.0021(6) 0.0029(7) O1 0.0191(6) 0.0435(7) 0.0407(7) -0.0039(6) 0.0038(4) -0.0037(5) O2 0.0236(6) 0.0334(7) 0.0282(6) 0.0019(5) 0.0070(4) -0.0023(5) F1 0.0352(6) 0.0400(6) 0.0402(6) 0.0001(4) 0.0163(4) -0.0089(4) F2 0.0578(7) 0.0317(6) 0.0364(6) 0.0097(4) 0.0121(4) 0.0099(5) F3 0.0207(5) 0.0481(6) 0.0285(5) -0.0002(4) 0.0012(3) 0.0010(4) _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 O1 1.2166(18) . ? C1 C13 1.505(2) . ? C1 C2 1.528(2) . ? C2 O2 1.4157(18) . ? C2 C6 1.536(2) . ? C3 O2 1.4414(19) . ? C3 C4 1.510(3) . ? C4 C5 1.521(2) . ? C5 C6 1.537(2) . ? C6 C7 1.525(2) . ? C7 F3 1.3665(17) . ? C7 F2 1.3801(18) . ? C7 C8 1.490(2) . ? C8 C9 1.311(2) . ? C8 F1 1.3575(17) . ? C9 C10 1.494(2) . ? C10 C11 1.531(2) . ? C11 C12 1.529(2) . ? C12 C13 1.530(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 O1 C1 C13 122.25(14) . . ? O1 C1 C2 117.36(14) . . ? C13 C1 C2 120.08(13) . . ? O2 C2 C1 111.08(13) . . ? O2 C2 C6 111.94(12) . . ? C1 C2 C6 115.35(12) . . ? O2 C3 C4 111.66(13) . . ? C3 C4 C5 110.85(14) . . ? C4 C5 C6 112.51(14) . . ? C7 C6 C2 114.33(13) . . ? C7 C6 C5 112.88(13) . . ? C2 C6 C5 108.26(13) . . ? F3 C7 F2 105.05(11) . . ? F3 C7 C8 108.03(12) . . ? F2 C7 C8 108.90(12) . . ? F3 C7 C6 111.77(12) . . ? F2 C7 C6 107.92(12) . . ? C8 C7 C6 114.70(13) . . ? C9 C8 F1 121.84(14) . . ? C9 C8 C7 127.04(14) . . ? F1 C8 C7 110.75(13) . . ? C8 C9 C10 126.60(15) . . ? C9 C10 C11 111.30(14) . . ? C12 C11 C10 116.54(15) . . ? C11 C12 C13 116.09(14) . . ? C1 C13 C12 114.75(14) . . ? C2 O2 C3 110.07(12) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.02 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.188 _refine_diff_density_min -0.213 _refine_diff_density_rms 0.041 #===END data_23b _database_code_depnum_ccdc_archive 'CCDC 219861' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C10 H10 Cl F5 O' _chemical_formula_weight 276.63 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M Pc loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x, -y, z+1/2' _cell_length_a 8.7576(4) _cell_length_b 13.7337(10) _cell_length_c 9.8743(4) _cell_angle_alpha 90.00 _cell_angle_beta 106.530(2) _cell_angle_gamma 90.00 _cell_volume 1138.54(11) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 12683 _cell_measurement_theta_min 2.97 _cell_measurement_theta_max 25.02 _exptl_crystal_description Block _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.614 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 560 _exptl_absorpt_coefficient_mu 0.383 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.793 _exptl_absorpt_correction_T_max 0.903 _exptl_absorpt_process_details 'SORTAV (Blessing, 1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker Nonius FR591 Rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Nonius Kappa CCD Area detector' _diffrn_measurement_method '\f and \w scans to fill the asymmetric unit' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12683 _diffrn_reflns_av_R_equivalents 0.0378 _diffrn_reflns_av_sigmaI/netI 0.0384 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.97 _diffrn_reflns_theta_max 25.02 _reflns_number_total 3794 _reflns_number_gt 3664 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Hooft, 1998)' _computing_cell_refinement 'DENZO (Otwinowski and MInor, 1997)' _computing_data_reduction 'DENZO, COLLECT, MAXUS (Mackay et al., 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'CAMERON (Watkin, et al., 1993)' _computing_publication_material 'WINGX (Farrugia, 1998)' _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^)+(0.0248P)^2^+0.1440P] 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 SHELXL _refine_ls_extinction_coef 0.0061(15) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.01(4) _refine_ls_number_reflns 3794 _refine_ls_number_parameters 308 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0272 _refine_ls_R_factor_gt 0.0254 _refine_ls_wR_factor_ref 0.0604 _refine_ls_wR_factor_gt 0.0594 _refine_ls_goodness_of_fit_ref 1.068 _refine_ls_restrained_S_all 1.068 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl1 Cl 0.99174(6) 0.60358(4) 0.06611(5) 0.03638(14) Uani 1 1 d . A 1 F1 F 1.33979(13) 0.31461(8) -0.00545(10) 0.0277(3) Uani 1 1 d . A 1 F2 F 1.08564(13) 0.24039(8) 0.05582(11) 0.0332(3) Uani 1 1 d . A 1 F3 F 1.14987(14) 0.31162(8) 0.26267(11) 0.0313(3) Uani 1 1 d . A 1 F4 F 1.02923(13) 0.40765(8) -0.07859(10) 0.0269(2) Uani 1 1 d . A 1 F5 F 0.90899(14) 0.39860(9) 0.08542(12) 0.0347(3) Uani 1 1 d . A 1 O1 O 1.29507(15) 0.52611(9) -0.02437(11) 0.0258(3) Uani 1 1 d . A 1 C1 C 1.3266(2) 0.32915(12) 0.12684(18) 0.0211(4) Uani 1 1 d . A 1 C2 C 1.4463(2) 0.35870(13) 0.23179(18) 0.0223(4) Uani 1 1 d . A 1 H2 H 1.4283 0.3655 0.3218 0.027 Uiso 1 1 calc R A 1 C3 C 1.6093(2) 0.38263(15) 0.2208(2) 0.0298(4) Uani 1 1 d . A 1 H3A H 1.6078 0.3811 0.1202 0.036 Uiso 1 1 calc R A 1 H3B H 1.6852 0.3322 0.2713 0.036 Uiso 1 1 calc R A 1 C4 C 1.6679(2) 0.48300(15) 0.2828(2) 0.0295(4) Uani 1 1 d . A 1 H4A H 1.6602 0.4854 0.3809 0.035 Uiso 1 1 calc R A 1 H4B H 1.7820 0.4890 0.2877 0.035 Uiso 1 1 calc R A 1 C5 C 1.5805(2) 0.57127(15) 0.2037(2) 0.0286(4) Uani 1 1 d . A 1 H5A H 1.5784 0.5657 0.1032 0.034 Uiso 1 1 calc R A 1 H5B H 1.6423 0.6304 0.2422 0.034 Uiso 1 1 calc R A 1 C6 C 1.4086(2) 0.58497(13) 0.21090(18) 0.0241(4) Uani 1 1 d . A 1 H6A H 1.4011 0.5593 0.3025 0.029 Uiso 1 1 calc R A 1 H6B H 1.3850 0.6556 0.2085 0.029 Uiso 1 1 calc R A 1 C7 C 1.2835(2) 0.53576(12) 0.09359(17) 0.0200(4) Uani 1 1 d . A 1 C8 C 1.1279(2) 0.50603(13) 0.12855(18) 0.0221(4) Uani 1 1 d . A 1 H8 H 1.1504 0.5015 0.2335 0.026 Uiso 1 1 calc R A 1 C9 C 1.0539(2) 0.41032(14) 0.06304(17) 0.0231(4) Uani 1 1 d . A 1 C10 C 1.1573(2) 0.32059(13) 0.12818(18) 0.0236(4) Uani 1 1 d . A 1 Cl1' Cl 0.57306(7) 0.85963(4) 0.59742(6) 0.04099(15) Uani 1 1 d . B 2 F1' F 0.81251(13) 1.18200(8) 0.47699(10) 0.0330(3) Uani 1 1 d . B 2 F2' F 0.53445(14) 1.22329(9) 0.52638(12) 0.0384(3) Uani 1 1 d . B 2 F3' F 0.62060(13) 1.17021(8) 0.74377(10) 0.0337(3) Uani 1 1 d . B 2 F4' F 0.54382(12) 1.04793(8) 0.42169(10) 0.0282(3) Uani 1 1 d . B 2 F5' F 0.41987(13) 1.04883(9) 0.58353(11) 0.0347(3) Uani 1 1 d . B 2 O1' O 0.84519(16) 0.96657(9) 0.49518(12) 0.0269(3) Uani 1 1 d . B 2 C1' C 0.8019(2) 1.17106(13) 0.61057(18) 0.0242(4) Uani 1 1 d . B 2 C2' C 0.9281(2) 1.16240(13) 0.72047(19) 0.0247(4) Uani 1 1 d . B 2 H2' H 0.9104 1.1574 0.8108 0.030 Uiso 1 1 calc R B 2 C3' C 1.0971(2) 1.15974(15) 0.7154(2) 0.0311(5) Uani 1 1 d . B 2 H3'1 H 1.1513 1.2204 0.7573 0.037 Uiso 1 1 calc R B 2 H3'2 H 1.0984 1.1572 0.6155 0.037 Uiso 1 1 calc R B 2 C4' C 1.1897(2) 1.07170(16) 0.79500(19) 0.0304(5) Uani 1 1 d . B 2 H4'1 H 1.3038 1.0806 0.8019 0.036 Uiso 1 1 calc R B 2 H4'2 H 1.1798 1.0720 0.8924 0.036 Uiso 1 1 calc R B 2 C5' C 1.1379(2) 0.97167(15) 0.73029(19) 0.0300(5) Uani 1 1 d . B 2 H5'1 H 1.2190 0.9232 0.7782 0.036 Uiso 1 1 calc R B 2 H5'2 H 1.1358 0.9733 0.6295 0.036 Uiso 1 1 calc R B 2 C6' C 0.9747(2) 0.93730(14) 0.73987(18) 0.0257(4) Uani 1 1 d . B 2 H6'1 H 0.9782 0.8657 0.7521 0.031 Uiso 1 1 calc R B 2 H6'2 H 0.9556 0.9661 0.8255 0.031 Uiso 1 1 calc R B 2 C7' C 0.8355(2) 0.96232(13) 0.61471(17) 0.0216(4) Uani 1 1 d . B 2 C8' C 0.6723(2) 0.97288(13) 0.64418(18) 0.0232(4) Uani 1 1 d . B 2 H8' H 0.6904 0.9839 0.7477 0.028 Uiso 1 1 calc R B 2 C9' C 0.5664(2) 1.05452(14) 0.56296(17) 0.0233(4) Uani 1 1 d . B 2 C10' C 0.6334(2) 1.15722(14) 0.61103(19) 0.0271(4) Uani 1 1 d . B 2 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 Cl1 0.0302(3) 0.0287(3) 0.0440(3) -0.0065(2) 0.00048(19) 0.0120(2) F1 0.0321(6) 0.0296(6) 0.0225(5) -0.0039(4) 0.0096(4) 0.0044(5) F2 0.0372(7) 0.0224(6) 0.0379(6) -0.0049(4) 0.0073(5) -0.0107(5) F3 0.0377(7) 0.0347(6) 0.0240(6) 0.0061(4) 0.0130(4) -0.0057(5) F4 0.0285(6) 0.0294(6) 0.0185(5) -0.0025(4) -0.0004(4) 0.0010(5) F5 0.0222(6) 0.0400(7) 0.0433(7) -0.0038(5) 0.0118(5) -0.0034(5) O1 0.0340(8) 0.0264(7) 0.0178(7) 0.0026(5) 0.0086(5) 0.0006(6) C1 0.0298(11) 0.0164(9) 0.0177(9) 0.0010(6) 0.0078(7) 0.0035(8) C2 0.0276(11) 0.0147(9) 0.0238(9) 0.0035(7) 0.0059(7) 0.0048(8) C3 0.0230(11) 0.0271(11) 0.0365(11) -0.0004(8) 0.0040(8) 0.0040(9) C4 0.0238(11) 0.0324(11) 0.0299(10) -0.0025(8) 0.0039(8) -0.0057(9) C5 0.0278(11) 0.0286(11) 0.0285(10) -0.0014(8) 0.0064(8) -0.0083(9) C6 0.0304(11) 0.0199(9) 0.0228(9) -0.0038(7) 0.0088(8) -0.0030(8) C7 0.0255(10) 0.0144(9) 0.0198(9) 0.0032(7) 0.0058(7) 0.0045(7) C8 0.0213(10) 0.0231(10) 0.0204(9) -0.0018(7) 0.0036(7) 0.0067(8) C9 0.0182(10) 0.0299(11) 0.0211(9) -0.0024(7) 0.0050(7) -0.0010(8) C10 0.0324(11) 0.0185(10) 0.0198(9) -0.0009(7) 0.0073(7) -0.0050(8) Cl1' 0.0434(3) 0.0268(3) 0.0509(3) 0.0018(2) 0.0104(2) -0.0173(2) F1' 0.0358(7) 0.0382(7) 0.0237(6) 0.0078(5) 0.0065(5) -0.0081(5) F2' 0.0376(7) 0.0309(7) 0.0400(7) 0.0041(5) 0.0003(5) 0.0120(5) F3' 0.0382(7) 0.0363(7) 0.0280(6) -0.0094(5) 0.0116(5) 0.0038(5) F4' 0.0285(6) 0.0366(6) 0.0178(5) -0.0012(4) 0.0038(4) -0.0032(5) F5' 0.0230(6) 0.0461(8) 0.0371(6) -0.0033(5) 0.0121(5) -0.0042(5) O1' 0.0357(8) 0.0293(8) 0.0184(7) -0.0026(5) 0.0121(5) -0.0023(6) C1' 0.0341(12) 0.0190(10) 0.0196(9) 0.0005(7) 0.0078(8) -0.0040(8) C2' 0.0313(11) 0.0159(9) 0.0260(9) -0.0018(7) 0.0069(8) -0.0036(8) C3' 0.0300(11) 0.0326(12) 0.0282(10) 0.0024(8) 0.0044(8) -0.0089(9) C4' 0.0235(11) 0.0412(13) 0.0248(10) -0.0008(8) 0.0044(8) -0.0012(9) C5' 0.0269(11) 0.0359(12) 0.0263(10) -0.0015(8) 0.0064(8) 0.0074(9) C6' 0.0319(11) 0.0262(10) 0.0209(9) 0.0018(7) 0.0105(8) 0.0067(9) C7' 0.0303(11) 0.0140(9) 0.0224(10) -0.0026(6) 0.0103(7) -0.0050(8) C8' 0.0267(10) 0.0226(10) 0.0213(9) -0.0012(7) 0.0083(7) -0.0100(8) C9' 0.0196(10) 0.0321(11) 0.0197(9) -0.0027(7) 0.0080(7) -0.0029(8) C10' 0.0312(12) 0.0223(10) 0.0260(10) 0.0000(8) 0.0053(8) 0.0042(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 Cl1 C8 1.7830(18) . ? F1 C1 1.3586(19) . ? F2 C10 1.365(2) . ? F3 C10 1.354(2) . ? F4 C9 1.354(2) . ? F5 C9 1.358(2) . ? O1 C7 1.205(2) . ? C1 C2 1.311(3) . ? C1 C10 1.491(3) . ? C2 C3 1.499(3) . ? C3 C4 1.536(3) . ? C4 C5 1.525(3) . ? C5 C6 1.539(3) . ? C6 C7 1.509(3) . ? C7 C8 1.552(3) . ? C8 C9 1.526(3) . ? C9 C10 1.556(3) . ? Cl1' C8' 1.7776(19) . ? F1' C1' 1.357(2) . ? F2' C10' 1.364(2) . ? F3' C10' 1.359(2) . ? F4' C9' 1.355(2) . ? F5' C9' 1.357(2) . ? O1' C7' 1.209(2) . ? C1' C2' 1.316(3) . ? C1' C10' 1.489(3) . ? C2' C3' 1.495(3) . ? C3' C4' 1.541(3) . ? C4' C5' 1.528(3) . ? C5' C6' 1.534(3) . ? C6' C7' 1.508(3) . ? C7' C8' 1.545(3) . ? C8' C9' 1.529(3) . ? C9' C10' 1.549(3) . ? 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 C1 F1 122.52(17) . . ? C2 C1 C10 126.21(16) . . ? F1 C1 C10 110.73(14) . . ? C1 C2 C3 125.08(17) . . ? C2 C3 C4 112.63(17) . . ? C5 C4 C3 116.58(16) . . ? C4 C5 C6 115.35(16) . . ? C7 C6 C5 114.59(15) . . ? O1 C7 C6 123.27(16) . . ? O1 C7 C8 120.44(15) . . ? C6 C7 C8 116.04(14) . . ? C9 C8 C7 115.24(15) . . ? C9 C8 Cl1 109.82(12) . . ? C7 C8 Cl1 105.57(12) . . ? F4 C9 F5 106.44(13) . . ? F4 C9 C8 112.65(15) . . ? F5 C9 C8 109.70(14) . . ? F4 C9 C10 107.97(14) . . ? F5 C9 C10 107.46(15) . . ? C8 C9 C10 112.32(15) . . ? F3 C10 F2 107.26(14) . . ? F3 C10 C1 109.97(15) . . ? F2 C10 C1 111.68(15) . . ? F3 C10 C9 107.02(14) . . ? F2 C10 C9 107.20(15) . . ? C1 C10 C9 113.41(15) . . ? C2' C1' F1' 122.55(17) . . ? C2' C1' C10' 125.92(17) . . ? F1' C1' C10' 111.05(14) . . ? C1' C2' C3' 125.56(18) . . ? C2' C3' C4' 112.58(16) . . ? C5' C4' C3' 116.20(16) . . ? C4' C5' C6' 114.93(16) . . ? C7' C6' C5' 115.43(15) . . ? O1' C7' C6' 123.14(17) . . ? O1' C7' C8' 120.34(16) . . ? C6' C7' C8' 116.26(14) . . ? C9' C8' C7' 115.21(14) . . ? C9' C8' Cl1' 109.05(13) . . ? C7' C8' Cl1' 106.21(13) . . ? F4' C9' F5' 106.45(13) . . ? F4' C9' C8' 112.34(15) . . ? F5' C9' C8' 109.73(15) . . ? F4' C9' C10' 107.92(14) . . ? F5' C9' C10' 107.36(15) . . ? C8' C9' C10' 112.73(15) . . ? F3' C10' F2' 106.95(15) . . ? F3' C10' C1' 109.88(15) . . ? F2' C10' C1' 111.75(15) . . ? F3' C10' C9' 106.68(14) . . ? F2' C10' C9' 107.37(15) . . ? C1' C10' C9' 113.86(15) . . ? _diffrn_measured_fraction_theta_max 0.985 _diffrn_reflns_theta_full 25.02 _diffrn_measured_fraction_theta_full 0.985 _refine_diff_density_max 0.227 _refine_diff_density_min -0.183 _refine_diff_density_rms 0.040 #===END data_24a _database_code_depnum_ccdc_archive 'CCDC 219862' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C10 H10 Cl F5 O' _chemical_formula_weight 276.63 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M P212121 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 7.9790(10) _cell_length_b 9.7420(10) _cell_length_c 14.053(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1092.4(2) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 6657 _cell_measurement_theta_min 2.94 _cell_measurement_theta_max 26.35 _exptl_crystal_description Block _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.3 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.682 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 560 _exptl_absorpt_coefficient_mu 0.399 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.834 _exptl_absorpt_correction_T_max 0.967 _exptl_absorpt_process_details 'SORTAV (Blessing, 1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker Nonius FR591 Rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Nonius Kappa CCD Area detector' _diffrn_measurement_method '\f and \w scans to fill the asymmetric unit' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6657 _diffrn_reflns_av_R_equivalents 0.0334 _diffrn_reflns_av_sigmaI/netI 0.0388 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.94 _diffrn_reflns_theta_max 26.35 _reflns_number_total 2190 _reflns_number_gt 2011 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Hooft, 1998)' _computing_cell_refinement 'DENZO (Otwinowski and MInor, 1997)' _computing_data_reduction 'DENZO, COLLECT, MAXUS (Mackay et al., 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'CAMERON (Watkin, et al., 1993)' _computing_publication_material 'WINGX (Farrugia, 1998)' _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^)+(0.0187P)^2^+0.2561P] 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 0.47(6) _refine_ls_number_reflns 2190 _refine_ls_number_parameters 155 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0334 _refine_ls_R_factor_gt 0.0283 _refine_ls_wR_factor_ref 0.0621 _refine_ls_wR_factor_gt 0.0598 _refine_ls_goodness_of_fit_ref 1.054 _refine_ls_restrained_S_all 1.054 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl1 Cl 0.14623(6) 0.49065(5) 0.53787(4) 0.03119(13) Uani 1 1 d . . . F3 F 0.36962(14) 0.65881(11) 0.67626(7) 0.0258(3) Uani 1 1 d . . . F2 F 0.56636(14) 0.55659(13) 0.75690(7) 0.0324(3) Uani 1 1 d . . . F4 F 0.53618(14) 0.32825(11) 0.65979(8) 0.0303(3) Uani 1 1 d . . . F1 F 0.76002(12) 0.52752(12) 0.60273(7) 0.0297(3) Uani 1 1 d . . . O1 O 0.44194(17) 0.70906(13) 0.48327(9) 0.0247(3) Uani 1 1 d . . . F5 F 0.29879(15) 0.39949(13) 0.71792(8) 0.0350(3) Uani 1 1 d . . . C4 C 0.5648(2) 0.5462(2) 0.32501(13) 0.0236(4) Uani 1 1 d . . . H4A H 0.4657 0.6039 0.3253 0.028 Uiso 1 1 calc R . . H4B H 0.6332 0.5735 0.2712 0.028 Uiso 1 1 calc R . . C6 C 0.5629(2) 0.63565(18) 0.49600(13) 0.0182(4) Uani 1 1 d . . . C5 C 0.6639(2) 0.57253(18) 0.41689(12) 0.0208(4) Uani 1 1 d . . . H5A H 0.7099 0.4861 0.4391 0.025 Uiso 1 1 calc R . . H5B H 0.7573 0.6328 0.4024 0.025 Uiso 1 1 calc R . . C9 C 0.4140(2) 0.42377(18) 0.64797(13) 0.0214(4) Uani 1 1 d . . . C7 C 0.6251(2) 0.61742(18) 0.59909(13) 0.0213(4) Uani 1 1 d . . . H7 H 0.6639 0.7071 0.6218 0.026 Uiso 1 1 calc R . . C10 C 0.3383(2) 0.40994(17) 0.55078(13) 0.0204(4) Uani 1 1 d . . . C1 C 0.4189(2) 0.34966(18) 0.47939(13) 0.0208(4) Uani 1 1 d . . . H1 H 0.5174 0.3039 0.4951 0.025 Uiso 1 1 calc R . . C2 C 0.3701(3) 0.3468(2) 0.37721(14) 0.0292(4) Uani 1 1 d . . . H2A H 0.2720 0.4041 0.3682 0.035 Uiso 1 1 calc R . . H2B H 0.3399 0.2536 0.3598 0.035 Uiso 1 1 calc R . . C8 C 0.4932(2) 0.56505(19) 0.66934(13) 0.0213(4) Uani 1 1 d . . . C3 C 0.5103(3) 0.3969(2) 0.31104(13) 0.0258(4) Uani 1 1 d . . . H3A H 0.6073 0.3384 0.3201 0.031 Uiso 1 1 calc R . . H3B H 0.4734 0.3856 0.2458 0.031 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 Cl1 0.0166(2) 0.0329(3) 0.0441(3) -0.0067(2) -0.0018(2) 0.0037(2) F3 0.0273(6) 0.0246(5) 0.0255(6) -0.0048(4) 0.0014(5) 0.0083(5) F2 0.0348(6) 0.0447(7) 0.0177(6) -0.0006(5) -0.0052(5) 0.0065(5) F4 0.0346(7) 0.0244(6) 0.0321(6) 0.0097(5) 0.0022(5) 0.0118(5) F1 0.0177(5) 0.0423(7) 0.0292(6) 0.0060(6) -0.0016(5) 0.0066(5) O1 0.0280(7) 0.0196(7) 0.0266(8) 0.0024(5) 0.0002(6) 0.0057(6) F5 0.0365(7) 0.0376(7) 0.0310(6) 0.0072(5) 0.0166(5) -0.0035(6) C4 0.0254(10) 0.0266(10) 0.0187(9) 0.0011(8) 0.0011(8) 0.0022(8) C6 0.0175(9) 0.0136(9) 0.0235(9) 0.0020(7) 0.0008(7) -0.0046(7) C5 0.0179(9) 0.0222(9) 0.0224(9) 0.0012(7) 0.0020(7) -0.0041(8) C9 0.0213(10) 0.0202(9) 0.0228(9) 0.0056(8) 0.0093(7) 0.0060(8) C7 0.0177(9) 0.0223(9) 0.0240(9) -0.0023(7) -0.0016(8) -0.0009(8) C10 0.0162(9) 0.0135(8) 0.0314(10) 0.0008(7) 0.0026(8) -0.0008(7) C1 0.0192(9) 0.0140(8) 0.0290(11) 0.0010(7) 0.0020(8) -0.0051(7) C2 0.0262(10) 0.0290(10) 0.0324(11) -0.0101(8) 0.0009(9) -0.0078(10) C8 0.0231(10) 0.0246(10) 0.0163(9) 0.0003(7) -0.0005(8) 0.0053(8) C3 0.0260(10) 0.0285(10) 0.0228(10) -0.0061(8) -0.0005(8) -0.0005(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 Cl1 C10 1.7319(17) . ? F3 C8 1.348(2) . ? F2 C8 1.364(2) . ? F4 C9 1.358(2) . ? F1 C7 1.389(2) . ? O1 C6 1.214(2) . ? F5 C9 1.366(2) . ? C4 C3 1.530(3) . ? C4 C5 1.536(2) . ? C6 C5 1.505(2) . ? C6 C7 1.542(2) . ? C9 C10 1.499(3) . ? C9 C8 1.544(3) . ? C7 C8 1.530(3) . ? C10 C1 1.328(3) . ? C1 C2 1.488(3) . ? C2 C3 1.535(3) . ? 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 C3 C4 C5 114.39(15) . . ? O1 C6 C5 123.89(16) . . ? O1 C6 C7 117.52(16) . . ? C5 C6 C7 118.34(15) . . ? C6 C5 C4 114.41(15) . . ? F4 C9 F5 106.04(13) . . ? F4 C9 C10 109.81(14) . . ? F5 C9 C10 111.64(15) . . ? F4 C9 C8 107.04(15) . . ? F5 C9 C8 106.85(15) . . ? C10 C9 C8 114.97(14) . . ? F1 C7 C8 107.39(14) . . ? F1 C7 C6 110.90(14) . . ? C8 C7 C6 115.04(15) . . ? C1 C10 C9 122.18(16) . . ? C1 C10 Cl1 123.36(15) . . ? C9 C10 Cl1 114.27(12) . . ? C10 C1 C2 127.62(18) . . ? C1 C2 C3 112.82(16) . . ? F3 C8 F2 106.78(14) . . ? F3 C8 C7 108.89(14) . . ? F2 C8 C7 107.94(15) . . ? F3 C8 C9 108.57(15) . . ? F2 C8 C9 107.25(15) . . ? C7 C8 C9 116.96(15) . . ? C4 C3 C2 115.58(16) . . ? _diffrn_measured_fraction_theta_max 0.984 _diffrn_reflns_theta_full 26.35 _diffrn_measured_fraction_theta_full 0.984 _refine_diff_density_max 0.141 _refine_diff_density_min -0.206 _refine_diff_density_rms 0.045 #===END data_24b _database_code_depnum_ccdc_archive 'CCDC 219863' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C10 H10 F6 O' _chemical_formula_weight 260.18 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 Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 5.9960(10) _cell_length_b 8.007(2) _cell_length_c 11.386(2) _cell_angle_alpha 80.90(3) _cell_angle_beta 87.03(3) _cell_angle_gamma 78.66(3) _cell_volume 529.10(18) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 6510 _cell_measurement_theta_min 2.96 _cell_measurement_theta_max 25.99 _exptl_crystal_description Block _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.633 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 264 _exptl_absorpt_coefficient_mu 0.175 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.876 _exptl_absorpt_correction_T_max 0.956 _exptl_absorpt_process_details 'SORTAV (Blessing, 1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker Nonius FR591 Rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Nonius Kappa CCD Area detector' _diffrn_measurement_method '\f and \w scans to fill the asymmetric unit' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6510 _diffrn_reflns_av_R_equivalents 0.0578 _diffrn_reflns_av_sigmaI/netI 0.0407 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.96 _diffrn_reflns_theta_max 25.99 _reflns_number_total 2053 _reflns_number_gt 1748 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Hooft, 1998)' _computing_cell_refinement 'DENZO (Otwinowski and MInor, 1997)' _computing_data_reduction 'DENZO, COLLECT, MAXUS (Mackay et al., 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'CAMERON (Watkin, et al., 1993)' _computing_publication_material 'WINGX (Farrugia, 1998)' _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^)+(0.0771P)^2^+0.0653P] 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 SHELXL _refine_ls_extinction_coef 0.030(13) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2053 _refine_ls_number_parameters 195 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0493 _refine_ls_R_factor_gt 0.0425 _refine_ls_wR_factor_ref 0.1248 _refine_ls_wR_factor_gt 0.1189 _refine_ls_goodness_of_fit_ref 1.059 _refine_ls_restrained_S_all 1.059 _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 0.96873(14) 0.09052(12) 0.36697(8) 0.0394(3) Uani 1 1 d . . . F2 F 0.60111(16) 0.32553(12) 0.30209(9) 0.0459(3) Uani 1 1 d . . . F3 F 0.38468(14) 0.13370(13) 0.32201(9) 0.0428(3) Uani 1 1 d . . . F4 F 0.84218(19) 0.19003(14) 0.12750(9) 0.0529(3) Uani 1 1 d . . . F5 F 0.4771(2) 0.24555(15) 0.09690(9) 0.0631(4) Uani 1 1 d . . . F6 F 0.45684(17) -0.09156(14) 0.15244(10) 0.0519(3) Uani 1 1 d . . . O1 O 0.60814(19) -0.21027(15) 0.40594(10) 0.0406(3) Uani 1 1 d . . . C1 C 0.7588(2) 0.04270(19) 0.38523(13) 0.0293(4) Uani 1 1 d . . . H1 H 0.698(3) 0.073(2) 0.4636(16) 0.038(4) Uiso 1 1 d . . . C2 C 0.5982(2) 0.15885(19) 0.29307(13) 0.0315(4) Uani 1 1 d . . . C3 C 0.6446(3) 0.1364(2) 0.16149(14) 0.0388(4) Uani 1 1 d . . . C4 C 0.6615(3) -0.0438(2) 0.13898(13) 0.0360(4) Uani 1 1 d . . . C5 C 0.8512(3) -0.1526(2) 0.12260(13) 0.0368(4) Uani 1 1 d . . . H5 H 0.995(3) -0.107(2) 0.1147(16) 0.039(4) Uiso 1 1 d . . . C6 C 0.8723(3) -0.3420(2) 0.12446(15) 0.0439(4) Uani 1 1 d . . . H6A H 0.904(3) -0.366(3) 0.0410(18) 0.051(5) Uiso 1 1 d . . . H6B H 0.721(4) -0.378(3) 0.1499(19) 0.052(5) Uiso 1 1 d . . . C7 C 1.0609(3) -0.4444(2) 0.20693(16) 0.0437(4) Uani 1 1 d . . . H7A H 1.203(3) -0.407(2) 0.1821(17) 0.045(5) Uiso 1 1 d . . . H7B H 1.080(4) -0.561(3) 0.1954(19) 0.061(6) Uiso 1 1 d . . . C8 C 1.0190(3) -0.4361(2) 0.33958(15) 0.0416(4) Uani 1 1 d . . . H8A H 0.879(4) -0.482(3) 0.3661(18) 0.055(6) Uiso 1 1 d . . . H8B H 1.145(4) -0.525(3) 0.3846(18) 0.054(5) Uiso 1 1 d . . . C9 C 1.0142(3) -0.2599(2) 0.37651(14) 0.0356(4) Uani 1 1 d . . . H9A H 1.070(4) -0.274(3) 0.4535(19) 0.055(6) Uiso 1 1 d . . . H9B H 1.116(3) -0.194(2) 0.3250(17) 0.040(5) Uiso 1 1 d . . . C10 C 0.7799(2) -0.15186(19) 0.38652(12) 0.0298(3) 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 0.0240(5) 0.0458(6) 0.0526(6) -0.0117(4) -0.0010(4) -0.0137(4) F2 0.0466(6) 0.0350(6) 0.0566(6) -0.0136(4) -0.0007(5) -0.0041(4) F3 0.0204(4) 0.0558(6) 0.0535(6) -0.0167(5) 0.0021(4) -0.0045(4) F4 0.0633(7) 0.0480(6) 0.0477(6) -0.0044(4) 0.0195(5) -0.0188(5) F5 0.0765(8) 0.0530(7) 0.0477(6) -0.0049(5) -0.0228(6) 0.0201(6) F6 0.0384(6) 0.0622(7) 0.0606(7) -0.0226(5) -0.0092(5) -0.0103(5) O1 0.0365(6) 0.0435(7) 0.0455(6) -0.0093(5) 0.0091(5) -0.0172(5) C1 0.0205(7) 0.0392(9) 0.0316(7) -0.0111(6) 0.0022(6) -0.0101(6) C2 0.0234(7) 0.0332(8) 0.0393(8) -0.0110(6) 0.0024(6) -0.0049(6) C3 0.0383(9) 0.0397(9) 0.0339(8) -0.0010(6) -0.0036(7) 0.0002(7) C4 0.0361(8) 0.0449(9) 0.0270(7) -0.0070(6) -0.0051(6) -0.0052(7) C5 0.0417(9) 0.0416(9) 0.0251(7) -0.0050(6) 0.0013(6) -0.0037(7) C6 0.0537(10) 0.0416(10) 0.0358(8) -0.0123(7) -0.0033(8) -0.0017(8) C7 0.0468(10) 0.0368(9) 0.0442(9) -0.0113(7) -0.0001(8) 0.0039(7) C8 0.0481(10) 0.0334(9) 0.0398(8) -0.0043(7) -0.0062(7) 0.0011(7) C9 0.0337(8) 0.0392(9) 0.0333(8) -0.0065(6) -0.0064(6) -0.0028(6) C10 0.0298(7) 0.0371(8) 0.0237(6) -0.0056(6) -0.0002(6) -0.0084(6) _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 1.3823(15) . ? F2 C2 1.3582(18) . ? F3 C2 1.3510(16) . ? F4 C3 1.355(2) . ? F5 C3 1.3572(19) . ? F6 C4 1.3499(19) . ? O1 C10 1.2088(18) . ? C1 C2 1.529(2) . ? C1 C10 1.536(2) . ? C1 H1 0.996(18) . ? C2 C3 1.542(2) . ? C3 C4 1.488(2) . ? C4 C5 1.314(2) . ? C5 C6 1.494(2) . ? C5 H5 0.993(19) . ? C6 C7 1.528(2) . ? C6 H6A 1.00(2) . ? C6 H6B 1.02(2) . ? C7 C8 1.528(2) . ? C7 H7A 0.97(2) . ? C7 H7B 0.95(2) . ? C8 C9 1.530(2) . ? C8 H8A 1.00(2) . ? C8 H8B 1.03(2) . ? C9 C10 1.507(2) . ? C9 H9A 0.94(2) . ? C9 H9B 0.991(19) . ? 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 F1 C1 C2 107.41(12) . . ? F1 C1 C10 111.12(12) . . ? C2 C1 C10 115.60(12) . . ? F1 C1 H1 107.4(10) . . ? C2 C1 H1 105.3(10) . . ? C10 C1 H1 109.5(10) . . ? F3 C2 F2 106.92(11) . . ? F3 C2 C1 108.03(12) . . ? F2 C2 C1 108.38(12) . . ? F3 C2 C3 107.81(12) . . ? F2 C2 C3 107.67(13) . . ? C1 C2 C3 117.57(12) . . ? F4 C3 F5 107.07(13) . . ? F4 C3 C4 109.55(13) . . ? F5 C3 C4 111.18(14) . . ? F4 C3 C2 107.43(13) . . ? F5 C3 C2 107.51(13) . . ? C4 C3 C2 113.82(13) . . ? C5 C4 F6 122.61(16) . . ? C5 C4 C3 125.70(16) . . ? F6 C4 C3 111.19(14) . . ? C4 C5 C6 125.56(17) . . ? C4 C5 H5 117.4(11) . . ? C6 C5 H5 116.9(11) . . ? C5 C6 C7 111.29(15) . . ? C5 C6 H6A 107.9(12) . . ? C7 C6 H6A 110.8(12) . . ? C5 C6 H6B 110.1(12) . . ? C7 C6 H6B 110.4(12) . . ? H6A C6 H6B 106.2(17) . . ? C8 C7 C6 116.03(15) . . ? C8 C7 H7A 109.0(12) . . ? C6 C7 H7A 109.1(11) . . ? C8 C7 H7B 108.3(13) . . ? C6 C7 H7B 107.0(14) . . ? H7A C7 H7B 107.0(17) . . ? C7 C8 C9 115.32(14) . . ? C7 C8 H8A 109.0(12) . . ? C9 C8 H8A 112.3(12) . . ? C7 C8 H8B 107.4(11) . . ? C9 C8 H8B 109.1(12) . . ? H8A C8 H8B 102.9(17) . . ? C10 C9 C8 114.78(13) . . ? C10 C9 H9A 103.2(13) . . ? C8 C9 H9A 109.7(13) . . ? C10 C9 H9B 110.9(10) . . ? C8 C9 H9B 111.7(10) . . ? H9A C9 H9B 105.7(16) . . ? O1 C10 C9 124.09(14) . . ? O1 C10 C1 117.27(13) . . ? C9 C10 C1 118.31(12) . . ? _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 25.99 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 0.286 _refine_diff_density_min -0.240 _refine_diff_density_rms 0.050 #===END data_24c _database_code_depnum_ccdc_archive 'CCDC 219864' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H20 F5 N O3' _chemical_formula_weight 357.32 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' N N 0.0061 0.0033 '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 P21/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 11.1132(2) _cell_length_b 11.0996(2) _cell_length_c 13.8507(3) _cell_angle_alpha 90.00 _cell_angle_beta 102.8902(12) _cell_angle_gamma 90.00 _cell_volume 1665.46(6) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 29759 _cell_measurement_theta_min 2.13 _cell_measurement_theta_max 26.39 _exptl_crystal_description Block _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.425 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 744 _exptl_absorpt_coefficient_mu 0.134 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.884 _exptl_absorpt_correction_T_max 0.987 _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker Nonius FR591 Rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Nonius Kappa CCD Area detector' _diffrn_measurement_method '\f and \w scans to fill the asymmetric unit' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 29759 _diffrn_reflns_av_R_equivalents 0.0446 _diffrn_reflns_av_sigmaI/netI 0.0245 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.13 _diffrn_reflns_theta_max 26.39 _reflns_number_total 3396 _reflns_number_gt 2809 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Hooft, 1998)' _computing_cell_refinement 'DENZO (Otwinowski and MInor, 1997)' _computing_data_reduction 'DENZO, COLLECT, MAXUS (Mackay et al., 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'CAMERON (Watkin, et al., 1993)' _computing_publication_material 'WINGX (Farrugia, 1998)' _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 w=1/[\s^2^(Fo^2^)+(0.0353P)^2^+0.5830P] 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 3396 _refine_ls_number_parameters 219 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0454 _refine_ls_R_factor_gt 0.0344 _refine_ls_wR_factor_ref 0.0854 _refine_ls_wR_factor_gt 0.0800 _refine_ls_goodness_of_fit_ref 1.040 _refine_ls_restrained_S_all 1.040 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group F4 F 0.63785(7) 0.69266(8) 0.07052(6) 0.0386(2) Uani 1 d . . . F1 F 0.73414(8) 0.45897(8) 0.06668(6) 0.0384(2) Uani 1 d . . . F3 F 0.90237(8) 0.68188(8) -0.02688(6) 0.0370(2) Uani 1 d . . . O2 O 0.94093(8) 0.81130(8) 0.15799(7) 0.0250(2) Uani 1 d . . . O3 O 0.85904(8) 0.98761(8) 0.19757(7) 0.0304(2) Uani 1 d . . . F5 F 0.73451(8) 0.83291(8) 0.00703(6) 0.0406(2) Uani 1 d . . . F2 F 0.71528(9) 0.61613(8) -0.08424(6) 0.0459(2) Uani 1 d . . . O1 O 1.04019(9) 0.56174(9) 0.13902(7) 0.0335(2) Uani 1 d . . . N1 N 1.05806(10) 0.97681(10) 0.18095(8) 0.0259(3) Uani 1 d . . . C6 C 0.94224(12) 0.51773(12) 0.14441(10) 0.0255(3) Uani 1 d . . . C5 C 0.91973(14) 0.45677(12) 0.23579(10) 0.0297(3) Uani 1 d . . . H5A H 0.9356 0.3694 0.2312 0.036 Uiso 1 calc R . . H5B H 0.8318 0.4668 0.2376 0.036 Uiso 1 calc R . . C11 C 0.94644(12) 0.93280(11) 0.18104(9) 0.0225(3) Uani 1 d . . . C3 C 0.93351(13) 0.58956(13) 0.39099(10) 0.0306(3) Uani 1 d . . . H3A H 0.9864 0.6011 0.4580 0.037 Uiso 1 calc R . . H3B H 0.8565 0.5499 0.3989 0.037 Uiso 1 calc R . . C10 C 0.83194(11) 0.75234(11) 0.16287(10) 0.0230(3) Uani 1 d . . . C9 C 0.75116(12) 0.73001(12) 0.06232(10) 0.0286(3) Uani 1 d . . . C8 C 0.80248(13) 0.63464(13) 0.00050(10) 0.0304(3) Uani 1 d . . . C12 C 1.16089(12) 0.90230(13) 0.16520(10) 0.0276(3) Uani 1 d . . . H12A H 1.1557 0.8219 0.1950 0.033 Uiso 1 calc R . . H12B H 1.2397 0.9398 0.1995 0.033 Uiso 1 calc R . . C7 C 0.83952(13) 0.51254(12) 0.04941(10) 0.0282(3) Uani 1 d . . . H7 H 0.8700 0.4613 0.0005 0.034 Uiso 1 calc R . . C2 C 0.90051(14) 0.71367(13) 0.34414(10) 0.0330(3) Uani 1 d . . . H2A H 0.8637 0.7634 0.3894 0.040 Uiso 1 calc R . . H2B H 0.9769 0.7542 0.3358 0.040 Uiso 1 calc R . . C1 C 0.81167(12) 0.70613(11) 0.24553(10) 0.0248(3) Uani 1 d . . . H1 H 0.7357 0.6654 0.2423 0.030 Uiso 1 calc R . . C14 C 1.07693(14) 1.10682(12) 0.19592(11) 0.0334(3) Uani 1 d . . . H14A H 0.9990 1.1492 0.1664 0.040 Uiso 1 calc R . . H14B H 1.1404 1.1340 0.1607 0.040 Uiso 1 calc R . . C4 C 0.99998(14) 0.50507(15) 0.33318(10) 0.0366(4) Uani 1 d . . . H4A H 1.0326 0.4357 0.3761 0.044 Uiso 1 calc R . . H4B H 1.0714 0.5484 0.3180 0.044 Uiso 1 calc R . . C15 C 1.11689(15) 1.14148(14) 0.30383(12) 0.0428(4) Uani 1 d . . . H15A H 1.0573 1.1101 0.3401 0.064 Uiso 1 calc R . . H15B H 1.1207 1.2295 0.3097 0.064 Uiso 1 calc R . . H15C H 1.1986 1.1074 0.3317 0.064 Uiso 1 calc R . . C13 C 1.16086(14) 0.88713(16) 0.05624(11) 0.0383(4) Uani 1 d . . . H13A H 1.0858 0.8446 0.0229 0.057 Uiso 1 calc R . . H13B H 1.2335 0.8405 0.0497 0.057 Uiso 1 calc R . . H13C H 1.1633 0.9666 0.0258 0.057 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 F4 0.0235(4) 0.0449(5) 0.0447(5) 0.0027(4) 0.0018(3) -0.0044(4) F1 0.0401(5) 0.0349(5) 0.0396(5) 0.0037(4) 0.0075(4) -0.0150(4) F3 0.0516(5) 0.0335(5) 0.0312(4) 0.0028(4) 0.0204(4) -0.0085(4) O2 0.0236(5) 0.0184(4) 0.0356(5) -0.0029(4) 0.0121(4) -0.0024(3) O3 0.0271(5) 0.0237(5) 0.0420(6) -0.0034(4) 0.0111(4) 0.0025(4) F5 0.0499(5) 0.0300(5) 0.0381(5) 0.0131(4) 0.0016(4) 0.0045(4) F2 0.0610(6) 0.0442(5) 0.0248(4) 0.0005(4) -0.0070(4) -0.0082(4) O1 0.0312(5) 0.0395(6) 0.0329(5) -0.0041(5) 0.0139(4) -0.0007(4) N1 0.0241(6) 0.0215(6) 0.0322(6) 0.0015(5) 0.0070(5) -0.0031(4) C6 0.0311(7) 0.0211(6) 0.0266(7) -0.0030(5) 0.0110(5) 0.0039(5) C5 0.0384(8) 0.0239(7) 0.0295(7) 0.0045(6) 0.0130(6) 0.0081(6) C11 0.0261(7) 0.0195(6) 0.0216(6) 0.0021(5) 0.0045(5) 0.0002(5) C3 0.0309(7) 0.0379(8) 0.0222(6) 0.0021(6) 0.0045(5) 0.0020(6) C10 0.0211(6) 0.0172(6) 0.0316(7) -0.0010(5) 0.0076(5) -0.0002(5) C9 0.0271(7) 0.0245(7) 0.0327(7) 0.0082(6) 0.0032(6) -0.0023(5) C8 0.0368(8) 0.0309(7) 0.0223(7) 0.0015(6) 0.0037(6) -0.0079(6) C12 0.0207(6) 0.0311(7) 0.0317(7) 0.0040(6) 0.0071(5) -0.0005(5) C7 0.0355(7) 0.0244(7) 0.0267(7) -0.0025(6) 0.0112(6) -0.0064(6) C2 0.0387(8) 0.0326(8) 0.0272(7) -0.0023(6) 0.0064(6) -0.0021(6) C1 0.0249(7) 0.0196(6) 0.0310(7) -0.0001(5) 0.0086(5) 0.0020(5) C14 0.0333(8) 0.0214(7) 0.0433(9) 0.0053(6) 0.0037(6) -0.0059(6) C4 0.0356(8) 0.0493(9) 0.0246(7) 0.0064(7) 0.0061(6) 0.0154(7) C15 0.0439(9) 0.0280(8) 0.0502(10) -0.0058(7) -0.0031(7) -0.0023(7) C13 0.0363(8) 0.0480(9) 0.0335(8) 0.0048(7) 0.0139(6) 0.0017(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 F4 C9 1.3544(15) . ? F1 C7 1.3811(15) . ? F3 C8 1.3561(16) . ? O2 C11 1.3840(15) . ? O2 C10 1.3916(15) . ? O3 C11 1.2105(15) . ? F5 C9 1.3645(16) . ? F2 C8 1.3606(16) . ? O1 C6 1.2105(16) . ? N1 C11 1.3334(16) . ? N1 C14 1.4663(17) . ? N1 C12 1.4658(17) . ? C6 C5 1.5046(19) . ? C6 C7 1.5387(19) . ? C5 C4 1.538(2) . ? C3 C4 1.526(2) . ? C3 C2 1.532(2) . ? C10 C1 1.3190(18) . ? C10 C9 1.4997(19) . ? C9 C8 1.548(2) . ? C8 C7 1.530(2) . ? C12 C13 1.5184(19) . ? C2 C1 1.4985(19) . ? C14 C15 1.511(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 C11 O2 C10 116.18(9) . . ? C11 N1 C14 117.65(11) . . ? C11 N1 C12 123.35(11) . . ? C14 N1 C12 118.99(11) . . ? O1 C6 C5 123.63(13) . . ? O1 C6 C7 117.91(12) . . ? C5 C6 C7 118.15(12) . . ? C6 C5 C4 114.11(12) . . ? O3 C11 N1 127.01(12) . . ? O3 C11 O2 122.50(11) . . ? N1 C11 O2 110.49(11) . . ? C4 C3 C2 115.37(12) . . ? C1 C10 O2 122.96(12) . . ? C1 C10 C9 124.00(12) . . ? O2 C10 C9 112.32(11) . . ? F4 C9 F5 106.92(10) . . ? F4 C9 C10 110.35(11) . . ? F5 C9 C10 111.16(11) . . ? F4 C9 C8 107.53(11) . . ? F5 C9 C8 106.41(11) . . ? C10 C9 C8 114.12(11) . . ? F3 C8 F2 106.69(11) . . ? F3 C8 C7 108.07(12) . . ? F2 C8 C7 108.52(11) . . ? F3 C8 C9 108.41(11) . . ? F2 C8 C9 107.52(12) . . ? C7 C8 C9 117.18(11) . . ? N1 C12 C13 112.53(11) . . ? F1 C7 C8 107.66(11) . . ? F1 C7 C6 111.34(11) . . ? C8 C7 C6 114.87(11) . . ? C1 C2 C3 112.49(12) . . ? C10 C1 C2 124.34(12) . . ? N1 C14 C15 113.06(12) . . ? C3 C4 C5 114.86(12) . . ? _diffrn_measured_fraction_theta_max 0.946 _diffrn_reflns_theta_full 26.39 _diffrn_measured_fraction_theta_full 0.946 _refine_diff_density_max 0.231 _refine_diff_density_min -0.232 _refine_diff_density_rms 0.039