# Supplementary Material (ESI) for Perkin Transactions # This journal is © The Royal Society of Chemistry 2000 # CCDC Number: 188/223 data_00srv092 _publ_contact_author 'Dr. David O'Hagan' _publ_contact_author_address ; Chemistry Department, University of Durham, South Rd., Durham DH1 3LE UK ; _publ_contact_author_email 'david.o'hagan@dur.ac.uk' _publ_contact_author_fax '0191 374 3745' _publ_contact_author_phone '0191 374 3119' _publ_contact_letter ; This paper will be send for publication in J.Chem.Soc.Perkin Trans. 2 ; _publ_requested_journal 'J.Chem.Soc.Perkin Trans. 2' _publ_section_title ; The preferred conformation of N-\b-fluoroethylamides. Observation of the fluorine amide gauche effect ; loop_ _publ_author_name _publ_author_address ; O'Hagan, David ; ; Chemistry Department, University of Durham, South Rd., Durham DH1 3LE UK ; ; Bilton, Clair ; ; Chemistry Department, University of Durham, South Rd., Durham DH1 3LE UK ; ; Howard, Judith A.K. ; ; Chemistry Department, University of Durham, South Rd., Durham DH1 3LE UK ; ; Knight, Lee ; ; Chemistry Department, University of Durham, South Rd., Durham DH1 3LE UK ; ; Tozer, David J. D. ; ; Chemistry Department, University of Durham, South Rd., Durham DH1 3LE UK ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C9 H8 F N3 O5' _chemical_formula_weight 257.18 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' '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 P2(1)/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 10.114(2) _cell_length_b 4.824(1) _cell_length_c 20.996(4) _cell_angle_alpha 90.00 _cell_angle_beta 93.60(3) _cell_angle_gamma 90.00 _cell_volume 1022.3(4) _cell_formula_units_Z 4 _cell_measurement_temperature 150 _cell_measurement_reflns_used 996 _cell_measurement_theta_min 10.13 _cell_measurement_theta_max 28.44 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.671 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 528 _exptl_absorpt_coefficient_mu 0.149 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.93 _exptl_absorpt_correction_T_max 0.99 _exptl_absorpt_process_details 'SADABS, Sheldrick, 1996??' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150 _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 '\w scans' _diffrn_detector_area_resol_mean 'not relevant' _diffrn_standards_number . _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% . _diffrn_reflns_number 6836 _diffrn_reflns_av_R_equivalents 0.0283 _diffrn_reflns_av_sigmaI/netI 0.0250 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 1.94 _diffrn_reflns_theta_max 27.49 _reflns_number_total 2331 _reflns_number_gt 1875 _reflns_threshold_expression >2sigma(I) _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.302 _refine_diff_density_min -0.253 _refine_diff_density_rms 0.054 _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXL-97 (Sheldrick, 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0448P)^2^+0.4786P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2331 _refine_ls_number_parameters 195 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0541 _refine_ls_R_factor_gt 0.0387 _refine_ls_wR_factor_ref 0.0969 _refine_ls_wR_factor_gt 0.0883 _refine_ls_goodness_of_fit_ref 1.062 _refine_ls_restrained_S_all 1.062 _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 C1 C 0.86353(15) 0.4920(3) 0.19343(7) 0.0190(3) Uani 1 1 d . . . H1 H 0.8331(19) 0.352(4) 0.2193(9) 0.027(5) Uiso 1 1 d . . . C2 C 0.98839(15) 0.6076(3) 0.20677(7) 0.0190(3) Uani 1 1 d . . . N1 N 1.07359(13) 0.4934(3) 0.26000(6) 0.0214(3) Uani 1 1 d . . . O1 O 1.04489(12) 0.2639(3) 0.28054(6) 0.0285(3) Uani 1 1 d . . . O2 O 1.16869(11) 0.6333(3) 0.28059(6) 0.0284(3) Uani 1 1 d . . . C3 C 1.03887(15) 0.8196(3) 0.17104(7) 0.0187(3) Uani 1 1 d . . . H3 H 1.122(2) 0.893(4) 0.1826(9) 0.026(5) Uiso 1 1 d . . . C4 C 0.95799(14) 0.9118(3) 0.11931(7) 0.0178(3) Uani 1 1 d . . . N2 N 1.00763(13) 1.1366(3) 0.07946(6) 0.0205(3) Uani 1 1 d . . . O3 O 1.11877(11) 1.2298(3) 0.09392(6) 0.0307(3) Uani 1 1 d . . . O4 O 0.93527(12) 1.2204(3) 0.03458(6) 0.0301(3) Uani 1 1 d . . . C5 C 0.83226(15) 0.8055(3) 0.10396(7) 0.0175(3) Uani 1 1 d . . . H5 H 0.7834(19) 0.874(4) 0.0672(9) 0.024(5) Uiso 1 1 d . . . C6 C 0.78434(14) 0.5945(3) 0.14190(7) 0.0174(3) Uani 1 1 d . . . C7 C 0.64977(15) 0.4641(3) 0.12760(7) 0.0172(3) Uani 1 1 d . . . O5 O 0.62850(11) 0.2218(2) 0.14401(6) 0.0234(3) Uani 1 1 d . . . N3 N 0.55871(12) 0.6239(3) 0.09633(6) 0.0186(3) Uani 1 1 d . . . H3A H 0.576(2) 0.800(5) 0.0940(10) 0.034(6) Uiso 1 1 d . . . C8 C 0.42467(15) 0.5171(3) 0.08121(8) 0.0199(3) Uani 1 1 d . . . H8A H 0.4282(19) 0.384(4) 0.0470(9) 0.027(5) Uiso 1 1 d . . . H8B H 0.3940(17) 0.418(4) 0.1174(9) 0.021(5) Uiso 1 1 d . . . C9 C 0.32961(16) 0.7467(4) 0.06335(8) 0.0219(3) Uani 1 1 d . . . H9A H 0.2374(19) 0.673(4) 0.0541(9) 0.026(5) Uiso 1 1 d . . . H9B H 0.3317(19) 0.893(4) 0.0961(9) 0.027(5) Uiso 1 1 d . . . F1 F 0.36597(10) 0.8761(2) 0.00666(5) 0.0296(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 C1 0.0194(7) 0.0172(8) 0.0206(7) 0.0000(6) 0.0039(6) 0.0022(6) C2 0.0177(7) 0.0221(8) 0.0171(7) -0.0012(6) -0.0006(6) 0.0052(6) N1 0.0192(6) 0.0260(7) 0.0188(6) 0.0001(6) -0.0002(5) 0.0057(6) O1 0.0314(7) 0.0280(7) 0.0256(6) 0.0070(5) -0.0011(5) 0.0038(5) O2 0.0205(6) 0.0354(7) 0.0283(6) -0.0007(5) -0.0070(5) 0.0008(5) C3 0.0148(7) 0.0195(8) 0.0215(7) -0.0035(6) 0.0005(6) 0.0018(6) C4 0.0166(7) 0.0161(7) 0.0207(7) 0.0006(6) 0.0022(6) 0.0007(6) N2 0.0168(6) 0.0186(7) 0.0263(7) 0.0002(6) 0.0025(5) -0.0004(5) O3 0.0194(6) 0.0298(7) 0.0426(7) 0.0075(6) -0.0012(5) -0.0078(5) O4 0.0257(6) 0.0333(7) 0.0309(6) 0.0134(6) -0.0029(5) -0.0023(5) C5 0.0161(7) 0.0177(7) 0.0188(7) 0.0000(6) 0.0001(6) 0.0025(6) C6 0.0141(7) 0.0175(7) 0.0206(7) -0.0006(6) 0.0007(6) 0.0019(6) C7 0.0171(7) 0.0176(7) 0.0170(7) -0.0002(6) 0.0027(5) -0.0006(6) O5 0.0211(6) 0.0178(6) 0.0311(6) 0.0045(5) 0.0008(5) -0.0010(5) N3 0.0148(6) 0.0158(6) 0.0249(7) 0.0019(5) -0.0012(5) -0.0019(5) C8 0.0161(7) 0.0204(8) 0.0229(8) 0.0019(7) -0.0013(6) -0.0039(6) C9 0.0168(7) 0.0252(8) 0.0236(8) 0.0033(7) 0.0011(6) -0.0006(6) F1 0.0256(5) 0.0329(6) 0.0300(5) 0.0121(4) -0.0004(4) -0.0008(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 C2 1.393(2) . ? C1 C6 1.396(2) . ? C2 C3 1.385(2) . ? C2 N1 1.475(2) . ? N1 O1 1.2292(19) . ? N1 O2 1.2309(18) . ? C3 C4 1.391(2) . ? C4 C5 1.390(2) . ? C4 N2 1.477(2) . ? N2 O4 1.2248(18) . ? N2 O3 1.2309(17) . ? C5 C6 1.398(2) . ? C6 C7 1.512(2) . ? C7 O5 1.2409(19) . ? C7 N3 1.341(2) . ? N3 C8 1.4662(19) . ? C8 C9 1.499(2) . ? C9 F1 1.4128(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 C2 C1 C6 118.88(15) . . ? C3 C2 C1 123.18(14) . . ? C3 C2 N1 117.95(14) . . ? C1 C2 N1 118.83(15) . . ? O1 N1 O2 124.54(14) . . ? O1 N1 C2 117.55(13) . . ? O2 N1 C2 117.90(14) . . ? C2 C3 C4 116.13(14) . . ? C5 C4 C3 123.20(15) . . ? C5 C4 N2 118.56(13) . . ? C3 C4 N2 118.23(13) . . ? O4 N2 O3 124.17(14) . . ? O4 N2 C4 118.04(13) . . ? O3 N2 C4 117.78(13) . . ? C4 C5 C6 118.77(14) . . ? C1 C6 C5 119.82(14) . . ? C1 C6 C7 118.15(14) . . ? C5 C6 C7 121.99(13) . . ? O5 C7 N3 123.48(14) . . ? O5 C7 C6 120.42(14) . . ? N3 C7 C6 116.10(13) . . ? C7 N3 C8 120.10(13) . . ? N3 C8 C9 111.38(13) . . ? F1 C9 C8 109.89(13) . . ? data_99SRV155 _publ_contact_author 'Dr. David O'Hagan' _publ_contact_author_address ; Chemistry Department, University of Durham, South Rd., Durham DH1 3LE UK ; _publ_contact_author_email 'david.o'hagan@dur.ac.uk' _publ_contact_author_fax '0191 374 3745' _publ_contact_author_phone '0191 374 3119' _publ_contact_letter ; This paper will be send for publication in J.Chem.Soc.Perkin Trans. 2 ; _publ_requested_journal 'J.Chem.Soc.Perkin Trans. 2' _publ_section_title ; The preferred conformation of N-\b-fluoroethylamides. Observation of the fluorine amide gauche effect ; loop_ _publ_author_name _publ_author_address ; O'Hagan, David ; ; Chemistry Department, University of Durham, South Rd., Durham DH1 3LE UK ; ; Bilton, Clair ; ; Chemistry Department, University of Durham, South Rd., Durham DH1 3LE UK ; ; Howard, Judith A.K. ; ; Chemistry Department, University of Durham, South Rd., Durham DH1 3LE UK ; ; Knight, Lee ; ; Chemistry Department, University of Durham, South Rd., Durham DH1 3LE UK ; ; Tozer, David J. D. ; ; Chemistry Department, University of Durham, South Rd., Durham DH1 3LE UK ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C9 H9 F N2 O3' _chemical_formula_weight 212.18 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' '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 'orthorhombic' _symmetry_space_group_name_H-M 'Pna2(1)' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' 'x+1/2, -y+1/2, z' '-x+1/2, y+1/2, z+1/2' _cell_length_a 9.9569(3) _cell_length_b 20.4211(8) _cell_length_c 4.6421(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 943.88(6) _cell_formula_units_Z 4 _cell_measurement_temperature 150 _cell_measurement_reflns_used 993 _cell_measurement_theta_min 10.15 _cell_measurement_theta_max 22.41 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.5 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.493 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 440 _exptl_absorpt_coefficient_mu 0.126 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_correction_T_min 0.748 _exptl_absorpt_correction_T_max 0.994 _exptl_absorpt_process_details 'Psi-scans using Shelx97' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150 _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 'Bruker SMART CCD' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 'not relevant' _diffrn_standards_number . _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% . _diffrn_reflns_number 11457 _diffrn_reflns_av_R_equivalents 0.0465 _diffrn_reflns_av_sigmaI/netI 0.0400 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -27 _diffrn_reflns_limit_k_max 28 _diffrn_reflns_limit_l_min -6 _diffrn_reflns_limit_l_max 6 _diffrn_reflns_theta_min 1.99 _diffrn_reflns_theta_max 30.12 _reflns_number_total 2644 _reflns_number_gt 1906 _reflns_threshold_expression >2sigma(I) _diffrn_measured_fraction_theta_max 0.964 _diffrn_reflns_theta_full 30.12 _diffrn_measured_fraction_theta_full 0.964 _refine_diff_density_max 0.238 _refine_diff_density_min -0.268 _refine_diff_density_rms 0.049 _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXL-97 (Sheldrick, 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _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 -0.6(13) _refine_ls_number_reflns 2644 _refine_ls_number_parameters 185 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0799 _refine_ls_R_factor_gt 0.0480 _refine_ls_wR_factor_ref 0.1374 _refine_ls_wR_factor_gt 0.1197 _refine_ls_goodness_of_fit_ref 0.909 _refine_ls_restrained_S_all 0.908 _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 C1 C 0.0634(2) 0.86566(11) 0.5174(6) 0.0348(5) Uani 1 1 d . . . H1 H -0.028(3) 0.8524(12) 0.486(7) 0.042(7) Uiso 1 1 d . . . C2 C 0.0966(2) 0.91558(11) 0.7072(5) 0.0350(5) Uani 1 1 d . . . H2 H 0.030(3) 0.9341(14) 0.826(7) 0.046(7) Uiso 1 1 d . . . C3 C 0.2314(2) 0.93151(10) 0.7412(5) 0.0297(4) Uani 1 1 d . . . N1 N 0.26877(19) 0.98300(8) 0.9451(4) 0.0367(4) Uani 1 1 d . . . O1 O 0.17918(19) 1.01110(12) 1.0768(7) 0.0794(9) Uani 1 1 d . . . O2 O 0.38672(17) 0.99431(10) 0.9852(5) 0.0537(5) Uani 1 1 d . . . C4 C 0.3324(2) 0.89970(11) 0.5894(5) 0.0343(5) Uani 1 1 d . . . H4 H 0.429(3) 0.9090(13) 0.610(8) 0.049(8) Uiso 1 1 d . . . C5 C 0.29731(19) 0.84960(11) 0.4026(5) 0.0340(5) Uani 1 1 d . . . H5 H 0.368(3) 0.8288(13) 0.285(7) 0.044(7) Uiso 1 1 d . . . C6 C 0.16206(18) 0.83221(10) 0.3651(4) 0.0272(4) Uani 1 1 d . . . C7 C 0.11745(19) 0.77794(10) 0.1657(5) 0.0302(4) Uani 1 1 d . . . O3 O -0.00446(14) 0.76749(8) 0.1283(4) 0.0415(4) Uani 1 1 d . . . N2 N 0.21231(18) 0.74271(9) 0.0335(4) 0.0323(4) Uani 1 1 d . . . C8 C 0.1788(2) 0.68802(12) -0.1549(5) 0.0372(5) Uani 1 1 d . . . H8A H 0.090(3) 0.6937(12) -0.256(6) 0.038(7) Uiso 1 1 d . . . H8B H 0.245(3) 0.6868(11) -0.309(6) 0.036(7) Uiso 1 1 d . . . C9 C 0.1755(3) 0.62365(13) 0.0031(7) 0.0503(6) Uani 1 1 d . . . H9 H 0.154(3) 0.5901(13) -0.131(6) 0.035(6) Uiso 1 1 d . . . F1 F 0.2832(3) 0.60512(14) 0.1418(9) 0.0519(8) Uani 0.50 1 d P . . F2 F 0.1042(3) 0.62480(14) 0.2304(7) 0.0494(7) Uani 0.50 1 d P . . H2A H 0.293(3) 0.7479(14) 0.086(7) 0.047(8) Uiso 1 1 d . . . H99 H 0.2041 0.6187 0.0400 0.040 Uiso 0.50 1 d P . . H98 H 0.1580 0.6239 0.0588 0.040 Uiso 0.50 1 d P . . 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 0.0183(8) 0.0426(11) 0.0435(12) 0.0057(10) -0.0023(9) 0.0017(8) C2 0.0225(9) 0.0428(11) 0.0398(13) -0.0002(10) 0.0005(9) 0.0066(9) C3 0.0242(9) 0.0295(9) 0.0353(11) 0.0050(9) 0.0000(8) 0.0013(7) N1 0.0345(9) 0.0333(9) 0.0425(11) -0.0004(9) -0.0009(8) 0.0043(7) O1 0.0398(11) 0.0827(16) 0.116(2) -0.0588(16) 0.0018(13) 0.0101(10) O2 0.0314(8) 0.0615(11) 0.0681(14) -0.0217(11) -0.0018(8) -0.0064(8) C4 0.0207(8) 0.0370(11) 0.0453(14) -0.0019(10) 0.0008(8) -0.0016(8) C5 0.0168(8) 0.0393(11) 0.0461(12) 0.0001(10) 0.0025(8) -0.0006(8) C6 0.0193(8) 0.0321(9) 0.0302(10) 0.0066(9) -0.0029(7) -0.0016(7) C7 0.0203(9) 0.0354(10) 0.0349(10) 0.0064(9) -0.0027(8) -0.0033(7) O3 0.0173(6) 0.0532(10) 0.0541(10) -0.0027(8) -0.0044(7) -0.0061(6) N2 0.0196(7) 0.0414(9) 0.0359(10) -0.0010(8) -0.0037(7) -0.0043(7) C8 0.0253(10) 0.0524(14) 0.0338(11) -0.0083(10) -0.0020(9) -0.0014(9) C9 0.0593(16) 0.0427(12) 0.0488(15) -0.0147(13) -0.0125(14) 0.0093(12) F1 0.0351(13) 0.0446(15) 0.076(2) -0.0003(15) -0.0232(15) 0.0025(12) F2 0.0477(16) 0.0424(14) 0.0582(19) 0.0006(14) 0.0108(14) -0.0014(13) _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 C2 1.388(3) . ? C1 C6 1.390(3) . ? C1 H1 0.96(3) . ? C2 C3 1.390(3) . ? C2 H2 0.94(3) . ? C3 C4 1.389(3) . ? C3 N1 1.463(3) . ? N1 O2 1.211(3) . ? N1 O1 1.224(3) . ? C4 C5 1.386(4) . ? C4 H4 0.98(3) . ? C5 C6 1.404(2) . ? C5 H5 0.99(3) . ? C6 C7 1.511(3) . ? C7 O3 1.245(2) . ? C7 N2 1.336(3) . ? N2 C8 1.457(3) . ? N2 H2A 0.84(3) . ? C8 C9 1.506(4) . ? C8 H8A 1.01(3) . ? C8 H8B 0.97(3) . ? C9 F2 1.271(4) . ? C9 F1 1.307(4) . ? C9 H9 0.95(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 C6 121.05(19) . . ? C2 C1 H1 121.9(17) . . ? C6 C1 H1 117.0(17) . . ? C1 C2 C3 118.30(19) . . ? C1 C2 H2 119.8(17) . . ? C3 C2 H2 121.5(17) . . ? C4 C3 C2 122.1(2) . . ? C4 C3 N1 118.72(18) . . ? C2 C3 N1 119.14(19) . . ? O2 N1 O1 122.7(2) . . ? O2 N1 C3 118.87(18) . . ? O1 N1 C3 118.4(2) . . ? C5 C4 C3 118.70(19) . . ? C5 C4 H4 116.7(18) . . ? C3 C4 H4 124.6(19) . . ? C4 C5 C6 120.4(2) . . ? C4 C5 H5 118.8(17) . . ? C6 C5 H5 120.6(17) . . ? C1 C6 C5 119.4(2) . . ? C1 C6 C7 117.67(17) . . ? C5 C6 C7 122.94(18) . . ? O3 C7 N2 122.2(2) . . ? O3 C7 C6 119.87(19) . . ? N2 C7 C6 117.92(17) . . ? C7 N2 C8 121.74(18) . . ? C7 N2 H2A 118(2) . . ? C8 N2 H2A 119(2) . . ? N2 C8 C9 112.4(2) . . ? N2 C8 H8A 113.1(14) . . ? C9 C8 H8A 107.9(14) . . ? N2 C8 H8B 107.8(15) . . ? C9 C8 H8B 110.6(14) . . ? H8A C8 H8B 105(2) . . ?