# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2008 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'Sebastien Thibaudeau' _publ_contact_author_address ; UMR 6514 40 Avenue du Recteur Pineau Poitiers 86000 FRANCE ; _publ_contact_author_email SEBASTIEN.THIBAUDEAU@UNIV-POITIERS.FR _publ_section_title ; Cyclisation/Fluorination of dienes in superacid HF/SbF5: a new route to fluorinated piperidines. ; loop_ _publ_author_name 'Sebastien Thibaudeau' 'Diego Gamba-Sanchez' 'Marie-Paule Jouannetaud' 'J. Marrot' ; A.Martin-Mingot ; 'Emilie Vardelle' data_2e _database_code_depnum_ccdc_archive 'CCDC 670158' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C13 H17 F N2 O2' _chemical_formula_weight 252.29 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 Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.3802(11) _cell_length_b 7.2136(11) _cell_length_c 14.245(3) _cell_angle_alpha 96.205(7) _cell_angle_beta 93.734(8) _cell_angle_gamma 103.868(7) _cell_volume 629.95(19) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 8571 _cell_measurement_theta_min 3.30 _cell_measurement_theta_max 29.97 _exptl_crystal_description parallelepiped _exptl_crystal_colour yellow _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.330 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 268 _exptl_absorpt_coefficient_mu 0.100 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9763 _exptl_absorpt_correction_T_max 0.9960 _exptl_absorpt_process_details 'SADABS (Sheldrick, V2.10)' _exptl_special_details ; 'Blessing, Acta Cryst. (1995) A51, 33-38' ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean 512x512 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 26662 _diffrn_reflns_av_R_equivalents 0.0378 _diffrn_reflns_av_sigmaI/netI 0.0217 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.44 _diffrn_reflns_theta_max 30.08 _reflns_number_total 3642 _reflns_number_gt 2993 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker APEX2' _computing_data_reduction 'Bruker SAINT' _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^)+(0.0712P)^2^+0.1435P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3642 _refine_ls_number_parameters 164 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0492 _refine_ls_R_factor_gt 0.0380 _refine_ls_wR_factor_ref 0.1275 _refine_ls_wR_factor_gt 0.1125 _refine_ls_goodness_of_fit_ref 1.075 _refine_ls_restrained_S_all 1.075 _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 1.26809(11) 0.68588(10) 0.48066(5) 0.02296(17) Uani 1 1 d . . . N1 N 1.01914(14) 0.37072(12) 0.27679(6) 0.01575(19) Uani 1 1 d . . . C2 C 0.97053(17) 0.55594(14) 0.30773(8) 0.0177(2) Uani 1 1 d . . . H2A H 0.9038 0.5492 0.3685 0.021 Uiso 1 1 calc R . . H2B H 0.8657 0.5827 0.2599 0.021 Uiso 1 1 calc R . . C3 C 1.17775(18) 0.71801(15) 0.32040(8) 0.0189(2) Uani 1 1 d . . . H3A H 1.2356 0.7328 0.2581 0.023 Uiso 1 1 calc R . . H3B H 1.1433 0.8403 0.3442 0.023 Uiso 1 1 calc R . . C2' C 1.16329(17) 0.32607(14) 0.35110(7) 0.0168(2) Uani 1 1 d . . . H2'1 H 1.1882 0.1972 0.3330 0.020 Uiso 1 1 calc R . . H2'2 H 1.0948 0.3244 0.4115 0.020 Uiso 1 1 calc R . . C3' C 1.37850(17) 0.47743(15) 0.36401(7) 0.0175(2) Uani 1 1 d . . . H3'1 H 1.4739 0.4480 0.4149 0.021 Uiso 1 1 calc R . . H3'2 H 1.4504 0.4718 0.3046 0.021 Uiso 1 1 calc R . . C4 C 1.35007(17) 0.67947(15) 0.38917(7) 0.0172(2) Uani 1 1 d . . . C5 C 0.81961(17) 0.21750(15) 0.25684(8) 0.0184(2) Uani 1 1 d . . . H5A H 0.7290 0.2243 0.3103 0.022 Uiso 1 1 calc R . . H5B H 0.8567 0.0914 0.2522 0.022 Uiso 1 1 calc R . . C6 C 0.68959(17) 0.23005(14) 0.16591(7) 0.0163(2) Uani 1 1 d . . . C7 C 0.46479(17) 0.15693(15) 0.15642(7) 0.0176(2) Uani 1 1 d . . . H7 H 0.3950 0.1046 0.2080 0.021 Uiso 1 1 calc R . . C8 C 0.34155(16) 0.15955(14) 0.07251(8) 0.0174(2) Uani 1 1 d . . . H8 H 0.1886 0.1101 0.0662 0.021 Uiso 1 1 calc R . . C7' C 0.79080(16) 0.30608(15) 0.08945(8) 0.0176(2) Uani 1 1 d . . . H7' H 0.9436 0.3564 0.0955 0.021 Uiso 1 1 calc R . . C8' C 0.67150(17) 0.30916(14) 0.00501(7) 0.0171(2) Uani 1 1 d . . . H8' H 0.7406 0.3598 -0.0471 0.020 Uiso 1 1 calc R . . C9 C 0.44786(16) 0.23609(14) -0.00142(7) 0.0157(2) Uani 1 1 d . . . C10 C 1.56253(19) 0.83176(17) 0.39911(8) 0.0233(2) Uani 1 1 d . . . H10A H 1.5359 0.9588 0.4164 0.035 Uiso 1 1 calc R . . H10B H 1.6277 0.8296 0.3387 0.035 Uiso 1 1 calc R . . H10C H 1.6615 0.8055 0.4486 0.035 Uiso 1 1 calc R . . N2 N 0.32037(15) 0.23718(13) -0.09101(6) 0.01803(19) Uani 1 1 d . . . O1 O 0.12101(13) 0.18341(13) -0.09464(6) 0.0262(2) Uani 1 1 d . . . O2 O 0.41744(14) 0.29120(13) -0.15847(6) 0.0257(2) 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 0.0271(3) 0.0247(3) 0.0158(3) 0.0007(2) 0.0050(2) 0.0041(3) N1 0.0174(4) 0.0124(4) 0.0168(4) 0.0021(3) -0.0012(3) 0.0030(3) C2 0.0186(5) 0.0149(4) 0.0200(5) 0.0015(4) -0.0002(4) 0.0055(4) C3 0.0229(5) 0.0135(4) 0.0199(5) 0.0024(4) 0.0002(4) 0.0038(4) C2' 0.0194(5) 0.0150(4) 0.0167(5) 0.0034(4) 0.0003(4) 0.0055(4) C3' 0.0178(5) 0.0184(5) 0.0166(5) 0.0021(4) 0.0007(4) 0.0053(4) C4 0.0196(5) 0.0175(5) 0.0133(5) 0.0014(4) 0.0028(4) 0.0022(4) C5 0.0205(5) 0.0156(4) 0.0174(5) 0.0038(4) 0.0001(4) 0.0007(4) C6 0.0187(5) 0.0124(4) 0.0166(5) 0.0007(3) 0.0011(4) 0.0027(3) C7 0.0190(5) 0.0165(5) 0.0161(5) 0.0021(4) 0.0047(4) 0.0016(4) C8 0.0156(4) 0.0153(4) 0.0201(5) -0.0001(4) 0.0028(4) 0.0024(3) C7' 0.0155(4) 0.0173(5) 0.0195(5) 0.0028(4) 0.0028(4) 0.0024(4) C8' 0.0187(5) 0.0156(4) 0.0173(5) 0.0033(4) 0.0045(4) 0.0038(4) C9 0.0180(5) 0.0138(4) 0.0153(5) 0.0000(3) 0.0006(4) 0.0053(4) C10 0.0232(5) 0.0222(5) 0.0202(5) -0.0001(4) 0.0034(4) -0.0019(4) N2 0.0203(4) 0.0156(4) 0.0184(4) 0.0001(3) -0.0002(3) 0.0064(3) O1 0.0183(4) 0.0286(4) 0.0296(5) 0.0047(3) -0.0036(3) 0.0031(3) O2 0.0278(4) 0.0344(5) 0.0175(4) 0.0064(3) 0.0029(3) 0.0109(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 C4 1.4358(12) . ? N1 C5 1.4607(13) . ? N1 C2' 1.4693(13) . ? N1 C2 1.4713(13) . ? C2 C3 1.5263(15) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.5202(15) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C2' C3' 1.5219(14) . ? C2' H2'1 0.9900 . ? C2' H2'2 0.9900 . ? C3' C4 1.5192(14) . ? C3' H3'1 0.9900 . ? C3' H3'2 0.9900 . ? C4 C10 1.5139(15) . ? C5 C6 1.5152(14) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 C7 1.3965(14) . ? C6 C7' 1.3982(15) . ? C7 C8 1.3917(15) . ? C7 H7 0.9500 . ? C8 C9 1.3832(15) . ? C8 H8 0.9500 . ? C7' C8' 1.3861(15) . ? C7' H7' 0.9500 . ? C8' C9 1.3908(14) . ? C8' H8' 0.9500 . ? C9 N2 1.4699(13) . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? N2 O2 1.2255(13) . ? N2 O1 1.2335(12) . ? 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 N1 C2' 110.43(8) . . ? C5 N1 C2 110.63(8) . . ? C2' N1 C2 109.18(8) . . ? N1 C2 C3 110.30(8) . . ? N1 C2 H2A 109.6 . . ? C3 C2 H2A 109.6 . . ? N1 C2 H2B 109.6 . . ? C3 C2 H2B 109.6 . . ? H2A C2 H2B 108.1 . . ? C4 C3 C2 112.02(9) . . ? C4 C3 H3A 109.2 . . ? C2 C3 H3A 109.2 . . ? C4 C3 H3B 109.2 . . ? C2 C3 H3B 109.2 . . ? H3A C3 H3B 107.9 . . ? N1 C2' C3' 109.51(8) . . ? N1 C2' H2'1 109.8 . . ? C3' C2' H2'1 109.8 . . ? N1 C2' H2'2 109.8 . . ? C3' C2' H2'2 109.8 . . ? H2'1 C2' H2'2 108.2 . . ? C4 C3' C2' 112.23(9) . . ? C4 C3' H3'1 109.2 . . ? C2' C3' H3'1 109.2 . . ? C4 C3' H3'2 109.2 . . ? C2' C3' H3'2 109.2 . . ? H3'1 C3' H3'2 107.9 . . ? F1 C4 C10 106.48(8) . . ? F1 C4 C3' 106.91(8) . . ? C10 C4 C3' 112.64(9) . . ? F1 C4 C3 106.40(8) . . ? C10 C4 C3 113.45(9) . . ? C3' C4 C3 110.46(8) . . ? N1 C5 C6 112.79(8) . . ? N1 C5 H5A 109.0 . . ? C6 C5 H5A 109.0 . . ? N1 C5 H5B 109.0 . . ? C6 C5 H5B 109.0 . . ? H5A C5 H5B 107.8 . . ? C7 C6 C7' 119.05(9) . . ? C7 C6 C5 119.52(9) . . ? C7' C6 C5 121.38(9) . . ? C8 C7 C6 120.97(10) . . ? C8 C7 H7 119.5 . . ? C6 C7 H7 119.5 . . ? C9 C8 C7 118.18(9) . . ? C9 C8 H8 120.9 . . ? C7 C8 H8 120.9 . . ? C8' C7' C6 120.99(9) . . ? C8' C7' H7' 119.5 . . ? C6 C7' H7' 119.5 . . ? C7' C8' C9 118.21(9) . . ? C7' C8' H8' 120.9 . . ? C9 C8' H8' 120.9 . . ? C8 C9 C8' 122.59(9) . . ? C8 C9 N2 118.84(9) . . ? C8' C9 N2 118.56(9) . . ? C4 C10 H10A 109.5 . . ? C4 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C4 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? O2 N2 O1 123.23(9) . . ? O2 N2 C9 118.36(9) . . ? O1 N2 C9 118.40(9) . . ? _diffrn_measured_fraction_theta_max 0.986 _diffrn_reflns_theta_full 30.08 _diffrn_measured_fraction_theta_full 0.986 _refine_diff_density_max 0.454 _refine_diff_density_min -0.225 _refine_diff_density_rms 0.066 #===END data_2j _database_code_depnum_ccdc_archive 'CCDC 670159' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C13 H15 F N2 O3' _chemical_formula_weight 266.27 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' 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 Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.6927(3) _cell_length_b 8.2566(3) _cell_length_c 12.1565(5) _cell_angle_alpha 79.479(2) _cell_angle_beta 80.510(2) _cell_angle_gamma 78.922(2) _cell_volume 642.26(5) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 5746 _cell_measurement_theta_min 2.74 _cell_measurement_theta_max 24.88 _exptl_crystal_description parallelepiped _exptl_crystal_colour colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.377 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 280 _exptl_absorpt_coefficient_mu 0.108 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9683 _exptl_absorpt_correction_T_max 0.9935 _exptl_absorpt_process_details 'SADABS (Sheldrick, V2.10)' _exptl_special_details ; 'Blessing, Acta Cryst. (1995) A51, 33-38' ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean 512x512 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13438 _diffrn_reflns_av_R_equivalents 0.0256 _diffrn_reflns_av_sigmaI/netI 0.0164 _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 1.72 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2260 _reflns_number_gt 1917 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker APEX2' _computing_data_reduction 'Bruker SAINT' _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^)+(0.0777P)^2^+0.0821P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2260 _refine_ls_number_parameters 173 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0439 _refine_ls_R_factor_gt 0.0366 _refine_ls_wR_factor_ref 0.1315 _refine_ls_wR_factor_gt 0.1177 _refine_ls_goodness_of_fit_ref 1.136 _refine_ls_restrained_S_all 1.136 _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 0.11822(17) -0.04181(12) 0.81230(8) 0.0633(3) Uani 1 1 d . . . N1 N 0.05269(18) 0.20028(16) 0.55588(10) 0.0436(3) Uani 1 1 d . . . C2 C 0.2379(2) 0.0798(2) 0.57740(13) 0.0468(4) Uani 1 1 d . . . H2A H 0.3395 0.0864 0.5106 0.056 Uiso 1 1 calc R . . H2B H 0.2051 -0.0323 0.5936 0.056 Uiso 1 1 calc R . . C3 C 0.3257(3) 0.1141(2) 0.67572(15) 0.0542(4) Uani 1 1 d . . . H3A H 0.3771 0.2191 0.6548 0.065 Uiso 1 1 calc R . . H3B H 0.4406 0.0265 0.6927 0.065 Uiso 1 1 calc R . . C2' C -0.1074(2) 0.2005(2) 0.65366(14) 0.0541(5) Uani 1 1 d . . . H2'A H -0.1520 0.0925 0.6720 0.065 Uiso 1 1 calc R . . H2'B H -0.2250 0.2846 0.6357 0.065 Uiso 1 1 calc R . . C3' C -0.0272(3) 0.2366(2) 0.75366(15) 0.0647(5) Uani 1 1 d . . . H3'A H -0.0031 0.3513 0.7388 0.078 Uiso 1 1 calc R . . H3'B H -0.1310 0.2258 0.8192 0.078 Uiso 1 1 calc R . . C4 C 0.1685(3) 0.1225(2) 0.78018(14) 0.0539(4) Uani 1 1 d . . . C5 C 0.0211(2) 0.30295(18) 0.45859(12) 0.0382(4) Uani 1 1 d . . . C6 C 0.1959(2) 0.30992(17) 0.36354(12) 0.0367(3) Uani 1 1 d . . . C7 C 0.1627(2) 0.28017(19) 0.25984(12) 0.0427(4) Uani 1 1 d . . . H7 H 0.0389 0.2504 0.2528 0.051 Uiso 1 1 calc R . . C8 C 0.3117(2) 0.2943(2) 0.16702(12) 0.0455(4) Uani 1 1 d . . . H8 H 0.2906 0.2726 0.0978 0.055 Uiso 1 1 calc R . . C7' C 0.3797(2) 0.35830(18) 0.37301(12) 0.0401(4) Uani 1 1 d . . . H7' H 0.4023 0.3794 0.4421 0.048 Uiso 1 1 calc R . . C8' C 0.5286(2) 0.37516(19) 0.28045(12) 0.0413(4) Uani 1 1 d . . . H8' H 0.6510 0.4086 0.2862 0.050 Uiso 1 1 calc R . . C9 C 0.4920(2) 0.34133(18) 0.17941(12) 0.0404(4) Uani 1 1 d . . . C10 C 0.2513(5) 0.1558(3) 0.8805(2) 0.0953(8) Uani 1 1 d . . . H10A H 0.1489 0.1474 0.9457 0.143 Uiso 1 1 calc R . . H10B H 0.2858 0.2661 0.8651 0.143 Uiso 1 1 calc R . . H10C H 0.3719 0.0752 0.8945 0.143 Uiso 1 1 calc R . . N2 N 0.6512(2) 0.35545(18) 0.08091(11) 0.0510(4) Uani 1 1 d . . . O1 O 0.6237(2) 0.3103(2) -0.00446(10) 0.0724(4) Uani 1 1 d . . . O2 O 0.8022(2) 0.41221(19) 0.08888(11) 0.0707(4) Uani 1 1 d . . . O3 O -0.14539(16) 0.39021(15) 0.44368(9) 0.0524(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 0.0824(8) 0.0493(6) 0.0574(6) 0.0005(4) -0.0124(5) -0.0148(5) N1 0.0364(6) 0.0471(7) 0.0410(7) -0.0036(5) -0.0001(5) 0.0013(5) C2 0.0427(8) 0.0445(8) 0.0445(8) -0.0038(6) -0.0004(6) 0.0061(6) C3 0.0483(9) 0.0539(10) 0.0595(10) 0.0004(8) -0.0134(8) -0.0095(7) C2' 0.0396(8) 0.0576(10) 0.0524(9) 0.0034(8) 0.0059(7) 0.0011(7) C3' 0.0807(13) 0.0555(10) 0.0462(9) -0.0087(8) 0.0091(9) 0.0036(9) C4 0.0749(11) 0.0423(9) 0.0471(9) -0.0069(7) -0.0120(8) -0.0130(8) C5 0.0364(7) 0.0409(8) 0.0395(8) -0.0115(6) -0.0093(6) -0.0031(6) C6 0.0386(7) 0.0341(7) 0.0365(7) -0.0061(6) -0.0089(6) 0.0001(6) C7 0.0428(8) 0.0483(8) 0.0405(8) -0.0093(6) -0.0122(6) -0.0078(6) C8 0.0540(9) 0.0520(9) 0.0327(7) -0.0096(6) -0.0123(6) -0.0055(7) C7' 0.0421(8) 0.0454(8) 0.0351(7) -0.0109(6) -0.0112(6) -0.0033(6) C8' 0.0376(7) 0.0435(8) 0.0433(8) -0.0050(6) -0.0105(6) -0.0051(6) C9 0.0431(8) 0.0396(8) 0.0337(7) -0.0016(6) -0.0053(6) 0.0007(6) C10 0.148(2) 0.0841(16) 0.0697(14) -0.0187(12) -0.0402(15) -0.0300(16) N2 0.0508(8) 0.0545(8) 0.0393(8) 0.0025(6) -0.0030(6) -0.0003(6) O1 0.0758(9) 0.0985(11) 0.0386(7) -0.0174(7) 0.0024(6) -0.0062(8) O2 0.0585(8) 0.0878(10) 0.0607(8) 0.0020(7) 0.0035(6) -0.0224(7) O3 0.0379(6) 0.0688(8) 0.0466(6) -0.0101(5) -0.0108(5) 0.0063(5) _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 C4 1.4301(19) . ? N1 C5 1.3451(19) . ? N1 C2 1.4603(19) . ? N1 C2' 1.4632(19) . ? C2 C3 1.507(2) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 C4 1.513(2) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C2' C3' 1.505(3) . ? C2' H2'A 0.9700 . ? C2' H2'B 0.9700 . ? C3' C4 1.503(3) . ? C3' H3'A 0.9700 . ? C3' H3'B 0.9700 . ? C4 C10 1.508(3) . ? C5 O3 1.2266(17) . ? C5 C6 1.504(2) . ? C6 C7 1.387(2) . ? C6 C7' 1.392(2) . ? C7 C8 1.381(2) . ? C7 H7 0.9300 . ? C8 C9 1.375(2) . ? C8 H8 0.9300 . ? C7' C8' 1.380(2) . ? C7' H7' 0.9300 . ? C8' C9 1.378(2) . ? C8' H8' 0.9300 . ? C9 N2 1.469(2) . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? N2 O1 1.2167(19) . ? N2 O2 1.2172(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 C5 N1 C2 126.47(12) . . ? C5 N1 C2' 120.59(12) . . ? C2 N1 C2' 112.94(12) . . ? N1 C2 C3 110.77(13) . . ? N1 C2 H2A 109.5 . . ? C3 C2 H2A 109.5 . . ? N1 C2 H2B 109.5 . . ? C3 C2 H2B 109.5 . . ? H2A C2 H2B 108.1 . . ? C2 C3 C4 112.34(14) . . ? C2 C3 H3A 109.1 . . ? C4 C3 H3A 109.1 . . ? C2 C3 H3B 109.1 . . ? C4 C3 H3B 109.1 . . ? H3A C3 H3B 107.9 . . ? N1 C2' C3' 110.32(14) . . ? N1 C2' H2'A 109.6 . . ? C3' C2' H2'A 109.6 . . ? N1 C2' H2'B 109.6 . . ? C3' C2' H2'B 109.6 . . ? H2'A C2' H2'B 108.1 . . ? C4 C3' C2' 113.20(14) . . ? C4 C3' H3'A 108.9 . . ? C2' C3' H3'A 108.9 . . ? C4 C3' H3'B 108.9 . . ? C2' C3' H3'B 108.9 . . ? H3'A C3' H3'B 107.8 . . ? F1 C4 C3' 106.29(15) . . ? F1 C4 C10 105.05(15) . . ? C3' C4 C10 114.17(17) . . ? F1 C4 C3 105.46(13) . . ? C3' C4 C3 111.19(14) . . ? C10 C4 C3 113.79(18) . . ? O3 C5 N1 122.64(13) . . ? O3 C5 C6 118.47(13) . . ? N1 C5 C6 118.89(12) . . ? C7 C6 C7' 119.41(13) . . ? C7 C6 C5 117.48(13) . . ? C7' C6 C5 122.88(12) . . ? C8 C7 C6 120.71(14) . . ? C8 C7 H7 119.6 . . ? C6 C7 H7 119.6 . . ? C9 C8 C7 118.41(13) . . ? C9 C8 H8 120.8 . . ? C7 C8 H8 120.8 . . ? C8' C7' C6 120.42(13) . . ? C8' C7' H7' 119.8 . . ? C6 C7' H7' 119.8 . . ? C9 C8' C7' 118.55(13) . . ? C9 C8' H8' 120.7 . . ? C7' C8' H8' 120.7 . . ? C8 C9 C8' 122.48(14) . . ? C8 C9 N2 118.48(13) . . ? C8' C9 N2 119.04(14) . . ? C4 C10 H10A 109.5 . . ? C4 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C4 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? O1 N2 O2 123.68(14) . . ? O1 N2 C9 117.91(14) . . ? O2 N2 C9 118.41(14) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.163 _refine_diff_density_min -0.232 _refine_diff_density_rms 0.045 #===END