# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2001 data_global _journal_coden_Cambridge 182 _publ_requested_journal 'ChemComm' loop_ _publ_author_name 'Percy, J.' 'Kariuki, Benson M.' 'Owton, W Martin' 'Pintat, Stephane' 'Smith, Clive A.' 'Thomas, Andrew C.' 'Watson, Martin' _publ_contact_author_name 'Dr J Percy' _publ_contact_author_address ; Department of Chemistry University of Leicester University Road Leicester LE1 7RH UK ; _publ_contact_author_email 'jmp29@le.ac.uk' _publ_section_title ; Rapid Assembly of Highly-functionalised Difluorinated Cyclooctenones via Ring-Closing Metathesis ; _publ_section_references ; SHELXL-93, Program for Crystal Structure Determination George M. Sheldrick, University of Gotingen, 1993. Molecular Structure Corporation. (1995). teXsan. Single Crystal Structure Analysis Software. Version 1.7. MSC, 3200 Research Forest Drive, The Woodlands, TX 77381, USA. Zachariasen, W. H. (1967). Acta Cryst. 23, 558-564. ; data_act1 #compound 12a _database_code_CSD 173277 _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety 'C15 H23 F2 N O4' _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C15 H23 F2 N O4' _chemical_formula_weight 319.34 _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' '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' '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' _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 10.063(5) _cell_length_b 11.594(5) _cell_length_c 7.484(3) _cell_angle_alpha 94.581(15) _cell_angle_beta 103.053(15) _cell_angle_gamma 88.349(8) _cell_volume 847.7(7) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 1914 _cell_measurement_theta_min 1.76 _cell_measurement_theta_max 25.18 _exptl_crystal_description block _exptl_crystal_colour white _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.251 _exptl_crystal_density_method ? _exptl_crystal_F_000 340 _exptl_absorpt_coefficient_mu 0.104 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Rigaku R-axis II' _diffrn_measurement_method 'Image plate scans' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4660 _diffrn_reflns_av_R_equivalents 0.0445 _diffrn_reflns_av_sigmaI/netI 0.0575 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 1.76 _diffrn_reflns_theta_max 25.18 _reflns_number_total 2681 _reflns_number_observed 1914 _reflns_observed_criterion >2sigma(I) _computing_data_collection 'MSC/AFC Diffractometer Control' _computing_cell_refinement 'MSC/AFC Diffractometer Control' _computing_data_reduction 'teXsan (MSC, 1995)' _computing_structure_solution 'SIR92 (Altomare, et. al. 1993)' _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 7 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^)+(0.1031P)^2^+0.2498P] 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 2674 _refine_ls_number_parameters 204 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0812 _refine_ls_R_factor_obs 0.0581 _refine_ls_wR_factor_all 0.1904 _refine_ls_wR_factor_obs 0.1498 _refine_ls_goodness_of_fit_all 0.851 _refine_ls_goodness_of_fit_obs 0.890 _refine_ls_restrained_S_all 0.947 _refine_ls_restrained_S_obs 0.890 _refine_ls_shift/esd_max -0.001 _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 1.1406(2) 0.2346(2) 0.8485(2) 0.0864(6) Uani 1 d . . F2 F 1.0415(2) 0.39800(14) 0.9008(2) 0.0848(5) Uani 1 d . . O1 O 1.2985(2) 0.3610(2) 1.1408(3) 0.0846(6) Uani 1 d . . O2 O 0.9069(2) 0.1524(2) 0.8482(2) 0.0684(5) Uani 1 d . . O3 O 0.7152(2) 0.25148(14) 1.0127(2) 0.0616(5) Uani 1 d . . O4 O 0.7346(2) 0.40313(15) 0.8482(3) 0.0731(6) Uani 1 d . . N1 N 0.5399(2) 0.2959(2) 0.7886(3) 0.0671(6) Uani 1 d . . C1 C 0.8551(2) 0.2656(2) 1.1075(3) 0.0572(6) Uani 1 d . . H1 H 0.8719(2) 0.3470(2) 1.1511(3) 0.069 Uiso 1 calc R . C2 C 0.8703(3) 0.1902(2) 1.2763(4) 0.0683(7) Uani 1 d . . C3 C 1.0138(3) 0.2029(3) 1.4025(4) 0.0815(9) Uani 1 d . . H3A H 1.0329(3) 0.2848(3) 1.4288(4) 0.098 Uiso 1 calc R . H3B H 1.0122(3) 0.1713(3) 1.5182(4) 0.098 Uiso 1 calc R . C4 C 1.1297(3) 0.1462(3) 1.3308(4) 0.0782(8) Uani 1 d . . H4 H 1.1517(3) 0.0704(3) 1.3594(4) 0.094 Uiso 1 calc R . C5 C 1.2039(3) 0.1942(2) 1.2301(4) 0.0728(8) Uani 1 d . . H5 H 1.2780(3) 0.1521(2) 1.2034(4) 0.087 Uiso 1 calc R . C6 C 1.1762(3) 0.3107(2) 1.1575(4) 0.0633(7) Uani 1 d . . H6 H 1.1340(3) 0.3608(2) 1.2415(4) 0.076 Uiso 1 calc R . C7 C 1.0767(3) 0.2939(2) 0.9711(4) 0.0605(6) Uani 1 d . . C8 C 0.9430(2) 0.2287(2) 0.9681(3) 0.0550(6) Uani 1 d . . C9 C 0.8403(3) 0.0636(2) 1.2114(4) 0.0805(9) Uani 1 d . . H9A H 0.7516(10) 0.0578(3) 1.1305(25) 0.121 Uiso 1 calc R . H9B H 0.8428(23) 0.0199(4) 1.3158(5) 0.121 Uiso 1 calc R . H9C H 0.9078(14) 0.0335(6) 1.1471(28) 0.121 Uiso 1 calc R . C10 C 0.7677(4) 0.2373(3) 1.3907(5) 0.1019(12) Uani 1 d . . H10A H 0.6773(5) 0.2364(22) 1.3138(10) 0.153 Uiso 1 calc R . H10B H 0.7910(16) 0.3151(9) 1.4386(31) 0.153 Uiso 1 calc R . H10C H 0.7710(20) 0.1895(14) 1.4907(22) 0.153 Uiso 1 calc R . C11 C 0.6669(2) 0.3237(2) 0.8789(3) 0.0571(6) Uani 1 d . . C12 C 0.4714(3) 0.3630(3) 0.6365(4) 0.0835(9) Uani 1 d . . H12A H 0.4250(3) 0.3106(3) 0.5356(4) 0.100 Uiso 1 calc R . H12B H 0.5391(3) 0.4044(3) 0.5934(4) 0.100 Uiso 1 calc R . C13 C 0.3711(4) 0.4470(4) 0.6903(6) 0.1187(14) Uani 1 d . . H13A H 0.3179(23) 0.4796(21) 0.5826(7) 0.178 Uiso 1 calc R . H13B H 0.4184(4) 0.5076(15) 0.7733(35) 0.178 Uiso 1 calc R . H13C H 0.3121(22) 0.4082(7) 0.7500(41) 0.178 Uiso 1 calc R . C14 C 0.4708(3) 0.1931(3) 0.8267(5) 0.0837(9) Uani 1 d . . H14A H 0.3728(3) 0.2042(3) 0.7891(5) 0.100 Uiso 1 calc R . H14B H 0.4934(3) 0.1844(3) 0.9580(5) 0.100 Uiso 1 calc R . C15 C 0.5117(4) 0.0846(3) 0.7271(7) 0.1220(15) Uani 1 d . . H15A H 0.4612(21) 0.0204(5) 0.7496(31) 0.183 Uiso 1 calc R . H15B H 0.6076(7) 0.0702(13) 0.7707(26) 0.183 Uiso 1 calc R . H15C H 0.4925(25) 0.0940(9) 0.5975(7) 0.183 Uiso 1 calc R . H16 H 1.2926(6) 0.4421(11) 1.1266(31) 0.142(16) Uiso 1 d 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 0.0656(10) 0.1126(14) 0.0809(11) -0.0118(9) 0.0216(8) -0.0095(9) F2 0.0720(10) 0.0802(11) 0.1009(12) 0.0405(9) 0.0042(9) -0.0070(8) O1 0.0629(12) 0.0680(13) 0.114(2) 0.0108(11) -0.0022(11) -0.0108(9) O2 0.0707(12) 0.0663(11) 0.0644(11) -0.0066(9) 0.0103(8) -0.0086(9) O3 0.0552(10) 0.0586(10) 0.0707(11) 0.0196(8) 0.0085(8) 0.0023(8) O4 0.0681(12) 0.0587(11) 0.0895(13) 0.0244(9) 0.0043(9) -0.0058(9) N1 0.0517(12) 0.0673(14) 0.0802(15) 0.0165(11) 0.0068(10) 0.0000(10) C1 0.0581(14) 0.0511(13) 0.0593(14) 0.0079(10) 0.0064(11) 0.0056(10) C2 0.075(2) 0.071(2) 0.061(2) 0.0177(12) 0.0155(12) 0.0120(13) C3 0.095(2) 0.088(2) 0.056(2) 0.0200(14) 0.0027(14) 0.009(2) C4 0.076(2) 0.074(2) 0.077(2) 0.0227(15) -0.0034(15) 0.0082(15) C5 0.065(2) 0.063(2) 0.079(2) 0.0073(14) -0.0074(14) 0.0074(13) C6 0.061(2) 0.0546(14) 0.068(2) 0.0028(12) 0.0016(12) -0.0004(12) C7 0.0543(14) 0.0593(14) 0.067(2) 0.0085(12) 0.0118(11) 0.0050(11) C8 0.0539(14) 0.0519(13) 0.0553(14) 0.0108(10) 0.0020(10) 0.0022(10) C9 0.085(2) 0.066(2) 0.092(2) 0.032(2) 0.017(2) 0.0015(15) C10 0.113(3) 0.122(3) 0.083(2) 0.029(2) 0.044(2) 0.027(2) C11 0.0541(14) 0.0518(13) 0.065(2) 0.0090(11) 0.0112(11) 0.0042(11) C12 0.063(2) 0.102(2) 0.079(2) 0.025(2) -0.0011(14) 0.003(2) C13 0.099(3) 0.118(3) 0.149(4) 0.059(3) 0.037(2) 0.043(2) C14 0.050(2) 0.084(2) 0.118(3) 0.016(2) 0.018(2) -0.0063(14) C15 0.109(3) 0.082(2) 0.171(4) -0.021(3) 0.031(3) -0.023(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 C7 1.367(3) . ? F2 C7 1.361(3) . ? O1 C6 1.412(3) . ? O2 C8 1.209(3) . ? O3 C11 1.353(3) . ? O3 C1 1.434(3) . ? O4 C11 1.228(3) . ? N1 C11 1.338(3) . ? N1 C12 1.460(4) . ? N1 C14 1.476(3) . ? C1 C8 1.541(3) . ? C1 C2 1.570(3) . ? C2 C9 1.526(4) . ? C2 C3 1.540(4) . ? C2 C10 1.545(4) . ? C3 C4 1.504(4) . ? C4 C5 1.334(4) . ? C5 C6 1.492(4) . ? C6 C7 1.524(4) . ? C7 C8 1.557(4) . ? C12 C13 1.481(5) . ? C14 C15 1.505(5) . ? 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 O3 C1 116.5(2) . . ? C11 N1 C12 119.4(2) . . ? C11 N1 C14 122.0(2) . . ? C12 N1 C14 118.4(2) . . ? O3 C1 C8 107.1(2) . . ? O3 C1 C2 103.9(2) . . ? C8 C1 C2 116.5(2) . . ? C9 C2 C3 110.8(2) . . ? C9 C2 C10 109.8(3) . . ? C3 C2 C10 107.0(3) . . ? C9 C2 C1 110.6(2) . . ? C3 C2 C1 110.7(2) . . ? C10 C2 C1 107.9(2) . . ? C4 C3 C2 116.7(3) . . ? C5 C4 C3 126.3(3) . . ? C4 C5 C6 124.5(3) . . ? O1 C6 C5 110.5(2) . . ? O1 C6 C7 111.1(2) . . ? C5 C6 C7 107.1(2) . . ? F2 C7 F1 105.0(2) . . ? F2 C7 C6 110.2(2) . . ? F1 C7 C6 109.4(2) . . ? F2 C7 C8 108.0(2) . . ? F1 C7 C8 107.6(2) . . ? C6 C7 C8 116.0(2) . . ? O2 C8 C1 121.2(2) . . ? O2 C8 C7 118.1(2) . . ? C1 C8 C7 120.6(2) . . ? O4 C11 N1 126.2(2) . . ? O4 C11 O3 122.4(2) . . ? N1 C11 O3 111.4(2) . . ? N1 C12 C13 112.3(3) . . ? N1 C14 C15 111.8(3) . . ? _refine_diff_density_max 0.165 _refine_diff_density_min -0.205 _refine_diff_density_rms 0.044 #===END data_act1b #compound 12b _database_code_CSD 173278 _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety 'C15 H23 F2 N O4' _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C15 H23 F2 N O4' _chemical_formula_weight 319.34 _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' '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/a loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z' '-x, -y, -z' 'x-1/2, -y-1/2, z' _cell_length_a 14.9117(12) _cell_length_b 7.5944(6) _cell_length_c 14.8779(11) _cell_angle_alpha 90.00 _cell_angle_beta 100.353(2) _cell_angle_gamma 90.00 _cell_volume 1657.4(2) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 2052 _cell_measurement_theta_min 1.39 _cell_measurement_theta_max 25.43 _exptl_crystal_description 'Hexagonal blocks' _exptl_crystal_colour white _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.280 _exptl_crystal_density_method ? _exptl_crystal_F_000 680 _exptl_absorpt_coefficient_mu 0.106 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Rigaku R-axis II' _diffrn_measurement_method 'Image plate scans' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7335 _diffrn_reflns_av_R_equivalents 0.0852 _diffrn_reflns_av_sigmaI/netI 0.0771 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.39 _diffrn_reflns_theta_max 25.43 _reflns_number_total 2882 _reflns_number_observed 2052 _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 1 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^)+(0.0996P)^2^+0.1072P] 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 0.0486(108) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 2881 _refine_ls_number_parameters 208 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0984 _refine_ls_R_factor_obs 0.0658 _refine_ls_wR_factor_all 0.2034 _refine_ls_wR_factor_obs 0.1742 _refine_ls_goodness_of_fit_all 1.081 _refine_ls_goodness_of_fit_obs 1.139 _refine_ls_restrained_S_all 1.113 _refine_ls_restrained_S_obs 1.139 _refine_ls_shift/esd_max 0.053 _refine_ls_shift/esd_mean 0.008 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 0.71027(15) 0.1332(2) 0.27485(14) 0.0898(7) Uani 1 d . . F2 F 0.59756(12) 0.2501(2) 0.18004(12) 0.0833(6) Uani 1 d . . O1 O 0.7741(2) 0.3622(3) 0.16000(14) 0.0763(7) Uani 1 d . . O2 O 0.6221(2) 0.2306(3) 0.39853(14) 0.0785(7) Uani 1 d . . O3 O 0.53305(12) 0.5693(2) 0.24595(11) 0.0565(5) Uani 1 d . . O4 O 0.41254(13) 0.3836(3) 0.22651(14) 0.0724(6) Uani 1 d . . N1 N 0.4294(2) 0.5839(3) 0.1171(2) 0.0754(8) Uani 1 d . . C1 C 0.5616(2) 0.5012(3) 0.3366(2) 0.0526(7) Uani 1 d . . H1 H 0.5064(2) 0.4725(3) 0.3608(2) 0.063 Uiso 1 calc R . C2 C 0.6110(2) 0.6525(4) 0.3961(2) 0.0588(7) Uani 1 d . . C3 C 0.6930(2) 0.7237(4) 0.3569(2) 0.0662(8) Uani 1 d . . H3A H 0.6735(2) 0.7437(4) 0.2920(2) 0.079 Uiso 1 calc R . H3B H 0.7103(2) 0.8368(4) 0.3850(2) 0.079 Uiso 1 calc R . C4 C 0.7761(2) 0.6073(4) 0.3701(2) 0.0704(8) Uani 1 d . . H4 H 0.8196(2) 0.6265(4) 0.4223(2) 0.084 Uiso 1 calc R . C5 C 0.7929(2) 0.4808(4) 0.3149(2) 0.0661(8) Uani 1 d . . H5 H 0.8483(2) 0.4218(4) 0.3299(2) 0.079 Uiso 1 calc R . C6 C 0.7297(2) 0.4251(4) 0.2298(2) 0.0593(7) Uani 1 d . . H6 H 0.6936(2) 0.5282(4) 0.2059(2) 0.071 Uiso 1 calc R . C7 C 0.6639(2) 0.2871(3) 0.2545(2) 0.0598(7) Uani 1 d . . C8 C 0.6160(2) 0.3315(3) 0.3356(2) 0.0562(7) Uani 1 d . . C9 C 0.6419(2) 0.5878(5) 0.4945(2) 0.0770(9) Uani 1 d . . H9A H 0.5899(3) 0.5481(24) 0.5187(5) 0.092 Uiso 1 calc R . H9B H 0.6710(12) 0.6825(9) 0.5314(4) 0.092 Uiso 1 calc R . H9C H 0.6841(11) 0.4922(18) 0.4950(3) 0.092 Uiso 1 calc R . C10 C 0.5412(2) 0.8006(5) 0.3963(2) 0.0848(10) Uani 1 d . . H10A H 0.5690(5) 0.8961(12) 0.4335(12) 0.102 Uiso 1 calc R . H10B H 0.4900(7) 0.7570(9) 0.4206(14) 0.102 Uiso 1 calc R . H10C H 0.5210(11) 0.8415(19) 0.3350(3) 0.102 Uiso 1 calc R . C11 C 0.4529(2) 0.5037(4) 0.1974(2) 0.0578(7) Uani 1 d . . C12 C 0.3415(2) 0.5387(5) 0.0607(2) 0.0834(10) Uani 1 d . . H12A H 0.3339(2) 0.4119(5) 0.0619(2) 0.100 Uiso 1 calc R . H12B H 0.3430(2) 0.5722(5) -0.0019(2) 0.100 Uiso 1 calc R . C13 C 0.2609(3) 0.6226(6) 0.0888(3) 0.1107(14) Uani 1 d . . H13A H 0.2064(3) 0.5834(29) 0.0493(12) 0.133 Uiso 1 calc R . H13B H 0.2657(10) 0.7482(6) 0.0846(18) 0.133 Uiso 1 calc R . H13C H 0.2584(11) 0.5902(30) 0.1507(7) 0.133 Uiso 1 calc R . C14 C 0.4887(3) 0.7233(6) 0.0816(3) 0.115(2) Uani 1 d . . H14A H 0.5527(3) 0.7003(6) 0.1049(3) 0.137 Uiso 1 calc R . H14B H 0.4790(3) 0.7203(6) 0.0154(3) 0.137 Uiso 1 calc R . C15 C 0.4644(5) 0.8861(8) 0.1112(4) 0.159(2) Uani 1 d . . H15A H 0.5008(18) 0.9758(10) 0.0897(22) 0.191 Uiso 1 calc R . H15B H 0.4745(26) 0.8879(19) 0.1767(4) 0.191 Uiso 1 calc R . H15C H 0.4012(7) 0.9078(23) 0.0876(22) 0.191 Uiso 1 calc R . H16 H 0.8157(43) 0.2771(69) 0.1762(36) 0.170(22) Uiso 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 0.1071(15) 0.0597(10) 0.1058(14) 0.0136(9) 0.0273(12) 0.0179(10) F2 0.0787(12) 0.0942(13) 0.0713(11) -0.0248(9) -0.0018(9) -0.0125(10) O1 0.0747(14) 0.093(2) 0.0617(12) 0.0105(11) 0.0145(11) 0.0215(13) O2 0.097(2) 0.0675(12) 0.0687(13) 0.0219(10) 0.0091(11) 0.0002(12) O3 0.0472(10) 0.0621(11) 0.0544(10) 0.0091(8) -0.0064(8) -0.0081(8) O4 0.0584(12) 0.0791(13) 0.0726(13) 0.0123(10) -0.0076(10) -0.0218(11) N1 0.068(2) 0.079(2) 0.069(2) 0.0194(13) -0.0166(12) -0.0192(14) C1 0.0458(14) 0.062(2) 0.0471(14) 0.0062(11) 0.0009(11) -0.0041(12) C2 0.056(2) 0.0611(15) 0.0558(15) -0.0047(12) 0.0012(12) -0.0048(13) C3 0.062(2) 0.064(2) 0.069(2) -0.0060(13) 0.0003(14) -0.0171(14) C4 0.050(2) 0.088(2) 0.067(2) -0.001(2) -0.0035(14) -0.0166(15) C5 0.047(2) 0.083(2) 0.064(2) 0.009(2) 0.0009(12) -0.0002(14) C6 0.055(2) 0.065(2) 0.057(2) 0.0074(12) 0.0064(12) 0.0073(13) C7 0.065(2) 0.0522(14) 0.057(2) 0.0016(12) -0.0021(13) 0.0048(13) C8 0.057(2) 0.0522(14) 0.0551(15) 0.0072(12) -0.0026(12) -0.0092(12) C9 0.078(2) 0.093(2) 0.056(2) -0.0095(15) 0.0004(15) -0.010(2) C10 0.082(2) 0.074(2) 0.095(2) -0.017(2) 0.007(2) 0.008(2) C11 0.0455(14) 0.064(2) 0.058(2) 0.0024(13) -0.0060(12) -0.0012(13) C12 0.071(2) 0.100(2) 0.067(2) 0.006(2) -0.022(2) -0.007(2) C13 0.072(2) 0.138(4) 0.111(3) 0.027(3) -0.015(2) 0.007(2) C14 0.126(4) 0.098(3) 0.095(3) 0.018(2) -0.045(3) -0.010(3) C15 0.169(6) 0.155(5) 0.144(5) -0.003(4) 0.005(4) -0.002(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 F1 C7 1.364(3) . ? F2 C7 1.375(3) . ? O1 C6 1.411(3) . ? O2 C8 1.200(3) . ? O3 C11 1.374(3) . ? O3 C1 1.435(3) . ? O4 C11 1.214(3) . ? N1 C11 1.331(3) . ? N1 C12 1.464(4) . ? N1 C14 1.532(5) . ? C1 C8 1.524(4) . ? C1 C2 1.554(4) . ? C2 C9 1.534(4) . ? C2 C10 1.532(4) . ? C2 C3 1.545(4) . ? C3 C4 1.505(4) . ? C4 C5 1.317(4) . ? C5 C6 1.498(4) . ? C6 C7 1.524(4) . ? C7 C8 1.547(4) . ? C12 C13 1.486(5) . ? C14 C15 1.382(7) . ? 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 O3 C1 116.5(2) . . ? C11 N1 C12 118.1(3) . . ? C11 N1 C14 123.4(3) . . ? C12 N1 C14 118.5(3) . . ? O3 C1 C8 111.4(2) . . ? O3 C1 C2 107.4(2) . . ? C8 C1 C2 115.6(2) . . ? C9 C2 C10 108.7(3) . . ? C9 C2 C3 110.5(2) . . ? C10 C2 C3 109.1(2) . . ? C9 C2 C1 109.7(2) . . ? C10 C2 C1 107.0(2) . . ? C3 C2 C1 111.7(2) . . ? C4 C3 C2 115.7(2) . . ? C5 C4 C3 126.3(3) . . ? C4 C5 C6 124.8(3) . . ? O1 C6 C5 114.2(2) . . ? O1 C6 C7 110.6(2) . . ? C5 C6 C7 109.0(2) . . ? F1 C7 F2 105.5(2) . . ? F1 C7 C6 108.7(2) . . ? F2 C7 C6 110.3(2) . . ? F1 C7 C8 107.4(2) . . ? F2 C7 C8 107.8(2) . . ? C6 C7 C8 116.5(2) . . ? O2 C8 C1 119.9(2) . . ? O2 C8 C7 119.2(2) . . ? C1 C8 C7 120.8(2) . . ? O4 C11 N1 126.6(3) . . ? O4 C11 O3 121.7(2) . . ? N1 C11 O3 111.7(2) . . ? N1 C12 C13 115.1(3) . . ? C15 C14 N1 108.0(5) . . ? _refine_diff_density_max 0.367 _refine_diff_density_min -0.291 _refine_diff_density_rms 0.047