# Copyright The Royal Society of Chemistry, 1999 # CCDC Number: 182/1092 data_eric3 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C19 H10 F11 N' _chemical_formula_weight 461.28 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' '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 'P 2(1)/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 10.217(2) _cell_length_b 8.6426(10) _cell_length_c 21.054(3) _cell_angle_alpha 90.00 _cell_angle_beta 101.22(2) _cell_angle_gamma 90.00 _cell_volume 1823.5(5) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description 'plate' _exptl_crystal_colour 'colourless' _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.680 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 920 _exptl_absorpt_coefficient_mu 0.178 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.9323 _exptl_absorpt_correction_T_max 0.9569 _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3378 _diffrn_reflns_av_R_equivalents 0.0159 _diffrn_reflns_av_sigmaI/netI 0.0449 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 1.97 _diffrn_reflns_theta_max 24.97 _reflns_number_total 3197 _reflns_number_gt 1926 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0535P)^2^+0.1305P] 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 3197 _refine_ls_number_parameters 320 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0974 _refine_ls_R_factor_gt 0.0389 _refine_ls_wR_factor_ref 0.1057 _refine_ls_wR_factor_gt 0.0857 _refine_ls_goodness_of_fit_ref 1.000 _refine_ls_restrained_S_all 1.000 _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 N1 N 0.65906(19) 0.5285(2) 0.83223(9) 0.0415(5) Uani 1 d . . . C2 C 0.6856(2) 0.5447(3) 0.90373(11) 0.0376(5) Uani 1 d . . . C3 C 0.8061(2) 0.6568(3) 0.91902(12) 0.0441(6) Uani 1 d . . . C4 C 0.8099(3) 0.7430(3) 0.85510(13) 0.0490(7) Uani 1 d . . . C5 C 0.7286(2) 0.6448(3) 0.80309(11) 0.0455(6) Uani 1 d . . . C6 C 0.7625(3) 0.4799(3) 0.79457(11) 0.0476(7) Uani 1 d . . . C7 C 0.5584(3) 0.6241(3) 0.91752(12) 0.0458(6) Uani 1 d . . . C8 C 0.6966(2) 0.3910(3) 0.93906(11) 0.0405(6) Uani 1 d . . . C9 C 0.7670(3) 0.3775(3) 1.00216(13) 0.0502(7) Uani 1 d . . . C10 C 0.7666(3) 0.2389(4) 1.03474(17) 0.0684(9) Uani 1 d . . . C11 C 0.6952(4) 0.1154(4) 1.0050(2) 0.0770(11) Uani 1 d . . . C12 C 0.6243(4) 0.1286(3) 0.94337(19) 0.0677(9) Uani 1 d . . . C13 C 0.6246(3) 0.2663(3) 0.91010(14) 0.0515(7) Uani 1 d . . . C14 C 0.6896(3) 0.4015(4) 0.73276(14) 0.0672(9) Uani 1 d . . . C15 C 0.8988(3) 0.4121(3) 0.81812(12) 0.0500(7) Uani 1 d . . . C16 C 0.9176(3) 0.2771(4) 0.85373(15) 0.0616(8) Uani 1 d . . . C17 C 1.0454(4) 0.2177(5) 0.87277(17) 0.0755(10) Uani 1 d . . . C18 C 1.1519(4) 0.2896(5) 0.85532(19) 0.0815(11) Uani 1 d . . . C19 C 1.1339(4) 0.4198(5) 0.81814(18) 0.0760(10) Uani 1 d . . . C20 C 1.0079(3) 0.4799(4) 0.79889(15) 0.0634(8) Uani 1 d . . . F3A F 0.92180(14) 0.57910(18) 0.93728(7) 0.0559(4) Uani 1 d . . . F3B F 0.79982(16) 0.75772(17) 0.96730(7) 0.0613(4) Uani 1 d . . . F4A F 0.93616(15) 0.77121(18) 0.84792(8) 0.0654(5) Uani 1 d . . . F4B F 0.75191(17) 0.88303(17) 0.85547(8) 0.0676(5) Uani 1 d . . . F5 F 0.65853(15) 0.72852(19) 0.75384(7) 0.0633(4) Uani 1 d . . . F7C F 0.56607(15) 0.64680(18) 0.98037(7) 0.0600(4) Uani 1 d . . . F7B F 0.45109(14) 0.53943(18) 0.89623(7) 0.0613(4) Uani 1 d . . . F7A F 0.53759(15) 0.76144(17) 0.88844(8) 0.0621(4) Uani 1 d . . . F14A F 0.57000(19) 0.4576(3) 0.70995(8) 0.0890(6) Uani 1 d . . . F14B F 0.7610(2) 0.4139(3) 0.68664(8) 0.1034(7) Uani 1 d . . . F14C F 0.6744(2) 0.2525(2) 0.74320(9) 0.0925(6) Uani 1 d . . . H9 H 0.814(3) 0.465(3) 1.0213(12) 0.053(8) Uiso 1 d . . . H10 H 0.818(3) 0.234(3) 1.0782(15) 0.075(10) Uiso 1 d . . . H11 H 0.695(3) 0.026(4) 1.0287(15) 0.081(10) Uiso 1 d . . . H12 H 0.576(3) 0.046(4) 0.9239(14) 0.069(9) Uiso 1 d . . . H13 H 0.570(3) 0.276(3) 0.8659(14) 0.062(8) Uiso 1 d . . . H16 H 0.845(3) 0.227(3) 0.8645(14) 0.068(10) Uiso 1 d . . . H17 H 1.058(3) 0.132(3) 0.8984(13) 0.056(9) Uiso 1 d . . . H18 H 1.235(4) 0.248(4) 0.8692(16) 0.095(12) Uiso 1 d . . . H19 H 1.206(4) 0.466(4) 0.8065(17) 0.095(12) Uiso 1 d . . . H20 H 0.997(3) 0.565(3) 0.7741(13) 0.064(9) 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 N1 0.0407(12) 0.0504(12) 0.0334(10) -0.0017(9) 0.0071(9) -0.0018(10) C2 0.0352(13) 0.0416(13) 0.0361(12) -0.0036(11) 0.0071(10) -0.0027(11) C3 0.0416(15) 0.0455(14) 0.0449(14) -0.0072(12) 0.0077(12) 0.0006(13) C4 0.0466(16) 0.0470(16) 0.0565(16) 0.0002(13) 0.0180(13) -0.0041(13) C5 0.0442(15) 0.0571(16) 0.0359(13) 0.0070(12) 0.0097(12) 0.0017(13) C6 0.0459(15) 0.0603(17) 0.0384(13) -0.0072(12) 0.0124(12) -0.0038(13) C7 0.0473(16) 0.0451(15) 0.0465(15) 0.0050(12) 0.0127(12) 0.0054(13) C8 0.0362(13) 0.0432(14) 0.0447(14) -0.0018(12) 0.0140(11) 0.0042(12) C9 0.0434(16) 0.0577(18) 0.0500(16) 0.0043(15) 0.0107(13) 0.0073(15) C10 0.061(2) 0.079(3) 0.067(2) 0.0277(19) 0.0177(17) 0.0216(19) C11 0.082(2) 0.056(2) 0.102(3) 0.031(2) 0.040(2) 0.018(2) C12 0.078(2) 0.0413(17) 0.092(3) -0.0039(19) 0.038(2) -0.0018(17) C13 0.0564(17) 0.0464(16) 0.0563(17) -0.0065(14) 0.0220(15) -0.0024(14) C14 0.076(2) 0.079(2) 0.0472(17) -0.0155(16) 0.0135(16) -0.0048(19) C15 0.0532(17) 0.0564(17) 0.0428(14) -0.0099(13) 0.0154(12) 0.0030(14) C16 0.064(2) 0.064(2) 0.0620(19) -0.0063(16) 0.0241(16) 0.0127(18) C17 0.083(3) 0.078(2) 0.069(2) 0.0024(19) 0.0244(19) 0.030(2) C18 0.057(2) 0.108(3) 0.082(2) -0.016(2) 0.019(2) 0.022(2) C19 0.055(2) 0.096(3) 0.082(2) -0.017(2) 0.0264(19) 0.002(2) C20 0.060(2) 0.075(2) 0.0609(19) -0.0049(18) 0.0248(16) 0.0006(18) F3A 0.0408(8) 0.0709(10) 0.0535(9) -0.0009(8) 0.0031(7) -0.0033(8) F3B 0.0745(11) 0.0579(9) 0.0525(9) -0.0211(8) 0.0148(8) -0.0114(8) F4A 0.0572(10) 0.0743(11) 0.0689(10) -0.0017(9) 0.0224(8) -0.0206(8) F4B 0.0821(12) 0.0466(9) 0.0786(11) 0.0050(8) 0.0265(9) 0.0002(9) F5 0.0645(10) 0.0750(11) 0.0497(9) 0.0203(8) 0.0098(8) 0.0060(9) F7C 0.0678(10) 0.0682(10) 0.0496(9) -0.0001(8) 0.0257(7) 0.0173(8) F7B 0.0370(8) 0.0701(10) 0.0776(11) 0.0017(9) 0.0131(7) -0.0014(8) F7A 0.0627(10) 0.0541(10) 0.0719(10) 0.0185(8) 0.0191(8) 0.0172(8) F14A 0.0773(13) 0.1152(16) 0.0626(11) -0.0240(11) -0.0162(9) 0.0029(12) F14B 0.1165(17) 0.153(2) 0.0475(10) -0.0354(12) 0.0326(10) -0.0284(15) F14C 0.1128(16) 0.0759(14) 0.0806(13) -0.0268(11) -0.0015(12) -0.0184(12) _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 N1 C5 1.436(3) . ? N1 C2 1.483(3) . ? N1 C6 1.499(3) . ? C2 C8 1.515(3) . ? C2 C7 1.546(3) . ? C2 C3 1.551(3) . ? C3 F3A 1.349(3) . ? C3 F3B 1.350(3) . ? C3 C4 1.545(4) . ? C4 F4B 1.348(3) . ? C4 F4A 1.350(3) . ? C4 C5 1.502(4) . ? C5 F5 1.350(3) . ? C5 C6 1.485(4) . ? C6 C15 1.503(4) . ? C6 C14 1.527(4) . ? C7 F7B 1.322(3) . ? C7 F7C 1.325(3) . ? C7 F7A 1.333(3) . ? C8 C13 1.378(4) . ? C8 C9 1.387(4) . ? C9 C10 1.381(4) . ? C10 C11 1.373(5) . ? C11 C12 1.361(5) . ? C12 C13 1.382(4) . ? C14 F14A 1.316(4) . ? C14 F14C 1.320(4) . ? C14 F14B 1.327(3) . ? C15 C16 1.380(4) . ? C15 C20 1.388(4) . ? C16 C17 1.388(5) . ? C17 C18 1.364(5) . ? C18 C19 1.363(5) . ? C19 C20 1.374(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 C5 N1 C2 111.09(18) . . ? C5 N1 C6 60.75(16) . . ? C2 N1 C6 123.70(18) . . ? N1 C2 C8 113.38(19) . . ? N1 C2 C7 103.78(18) . . ? C8 C2 C7 106.38(19) . . ? N1 C2 C3 104.50(18) . . ? C8 C2 C3 117.74(19) . . ? C7 C2 C3 110.24(19) . . ? F3A C3 F3B 105.94(19) . . ? F3A C3 C4 108.6(2) . . ? F3B C3 C4 110.9(2) . . ? F3A C3 C2 111.4(2) . . ? F3B C3 C2 114.0(2) . . ? C4 C3 C2 105.88(19) . . ? F4B C4 F4A 105.6(2) . . ? F4B C4 C5 109.3(2) . . ? F4A C4 C5 115.2(2) . . ? F4B C4 C3 110.0(2) . . ? F4A C4 C3 111.8(2) . . ? C5 C4 C3 105.0(2) . . ? F5 C5 N1 118.1(2) . . ? F5 C5 C6 121.5(2) . . ? N1 C5 C6 61.74(16) . . ? F5 C5 C4 113.1(2) . . ? N1 C5 C4 109.48(19) . . ? C6 C5 C4 121.4(2) . . ? C5 C6 N1 57.51(15) . . ? C5 C6 C15 123.9(2) . . ? N1 C6 C15 129.6(2) . . ? C5 C6 C14 116.3(2) . . ? N1 C6 C14 107.3(2) . . ? C15 C6 C14 112.0(2) . . ? F7B C7 F7C 107.7(2) . . ? F7B C7 F7A 106.8(2) . . ? F7C C7 F7A 107.5(2) . . ? F7B C7 C2 111.2(2) . . ? F7C C7 C2 111.4(2) . . ? F7A C7 C2 111.9(2) . . ? C13 C8 C9 119.4(2) . . ? C13 C8 C2 119.1(2) . . ? C9 C8 C2 121.3(2) . . ? C10 C9 C8 119.8(3) . . ? C11 C10 C9 120.0(3) . . ? C12 C11 C10 120.5(3) . . ? C11 C12 C13 120.1(3) . . ? C8 C13 C12 120.2(3) . . ? F14A C14 F14C 106.8(3) . . ? F14A C14 F14B 107.9(3) . . ? F14C C14 F14B 107.5(3) . . ? F14A C14 C6 114.3(3) . . ? F14C C14 C6 110.2(3) . . ? F14B C14 C6 110.0(3) . . ? C16 C15 C20 118.8(3) . . ? C16 C15 C6 122.1(3) . . ? C20 C15 C6 118.9(3) . . ? C15 C16 C17 119.6(4) . . ? C18 C17 C16 120.6(4) . . ? C19 C18 C17 120.4(4) . . ? C18 C19 C20 119.7(4) . . ? C19 C20 C15 120.9(4) . . ? _diffrn_measured_fraction_theta_max 0.932 _diffrn_reflns_theta_full 24.97 _diffrn_measured_fraction_theta_full 0.932 _refine_diff_density_max 0.179 _refine_diff_density_min -0.250 _refine_diff_density_rms 0.050 #=END data_beta _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C19 H11 F12 N' _chemical_formula_weight 481.29 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' '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 'Pbcn' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, z' 'x, -y, z+1/2' '-x+1/2, -y+1/2, z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, -z' '-x, y, -z-1/2' 'x-1/2, y-1/2, -z-1/2' _cell_length_a 27.339(2) _cell_length_b 8.3850(10) _cell_length_c 15.593(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3574.5(7) _cell_formula_units_Z 8 _cell_measurement_temperature 203(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description 'plate' _exptl_crystal_colour 'colourless' _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.789 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1920 _exptl_absorpt_coefficient_mu 0.193 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.9267 _exptl_absorpt_correction_T_max 0.9716 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 203(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3129 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0315 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 32 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.49 _diffrn_reflns_theta_max 24.97 _reflns_number_total 3129 _reflns_number_gt 2295 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0323P)^2^+1.5942P] 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 3129 _refine_ls_number_parameters 333 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0620 _refine_ls_R_factor_gt 0.0355 _refine_ls_wR_factor_ref 0.0808 _refine_ls_wR_factor_gt 0.0718 _refine_ls_goodness_of_fit_ref 1.029 _refine_ls_restrained_S_all 1.029 _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_symetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N 0.38082(7) 0.2214(2) 0.32397(12) 0.0226(4) Uani 1 1 d . . . C2 C 0.41641(8) 0.1508(3) 0.38296(13) 0.0248(5) Uani 1 1 d . . . C3 C 0.42647(8) -0.0240(3) 0.35631(14) 0.0287(5) Uani 1 1 d . . . C4 C 0.38223(8) -0.1201(3) 0.32543(15) 0.0307(5) Uani 1 1 d . . . C5 C 0.35047(8) -0.0286(3) 0.26105(14) 0.0274(5) Uani 1 1 d . . . C6 C 0.33810(7) 0.1457(2) 0.28526(13) 0.0231(5) Uani 1 1 d . . . C7 C 0.39931(8) 0.1614(3) 0.47783(14) 0.0331(6) Uani 1 1 d . . . C8 C 0.46270(8) 0.2552(3) 0.37853(13) 0.0251(5) Uani 1 1 d . . . C9 C 0.50931(8) 0.1941(3) 0.39105(15) 0.0333(6) Uani 1 1 d . . . C10 C 0.54936(9) 0.2930(3) 0.39173(16) 0.0378(6) Uani 1 1 d . . . C11 C 0.54405(9) 0.4542(3) 0.38045(17) 0.0415(6) Uani 1 1 d . . . C12 C 0.49817(10) 0.5164(3) 0.36956(19) 0.0451(7) Uani 1 1 d . . . C13 C 0.45782(9) 0.4185(3) 0.36889(16) 0.0354(6) Uani 1 1 d . . . C14 C 0.29266(8) 0.1562(3) 0.34456(14) 0.0289(5) Uani 1 1 d . . . C15 C 0.32432(7) 0.2455(3) 0.20562(13) 0.0233(5) Uani 1 1 d . . . C16 C 0.33103(8) 0.4094(3) 0.20786(14) 0.0262(5) Uani 1 1 d . . . C17 C 0.31905(8) 0.5026(3) 0.13797(15) 0.0315(5) Uani 1 1 d . . . C18 C 0.30024(9) 0.4331(3) 0.06486(15) 0.0343(6) Uani 1 1 d . . . C19 C 0.29201(9) 0.2716(3) 0.06323(15) 0.0369(6) Uani 1 1 d . . . C20 C 0.30371(8) 0.1783(3) 0.13303(15) 0.0308(5) Uani 1 1 d . . . F3A F 0.44839(5) -0.10794(16) 0.41981(9) 0.0405(4) Uani 1 1 d . . . F3B F 0.45757(4) -0.02261(16) 0.28879(8) 0.0355(3) Uani 1 1 d . . . F4A F 0.35509(5) -0.16998(16) 0.39167(9) 0.0418(4) Uani 1 1 d . . . F4B F 0.39864(5) -0.25346(15) 0.28656(9) 0.0425(4) Uani 1 1 d . . . F5A F 0.31014(5) -0.11723(15) 0.24552(9) 0.0391(3) Uani 1 1 d . . . F5B F 0.37718(5) -0.02660(15) 0.18762(8) 0.0341(3) Uani 1 1 d . . . F7A F 0.43687(5) 0.15236(18) 0.53167(8) 0.0423(4) Uani 1 1 d . . . F7B F 0.36871(6) 0.0480(2) 0.50172(8) 0.0545(4) Uani 1 1 d . . . F7C F 0.37774(6) 0.29990(18) 0.49225(8) 0.0511(4) Uani 1 1 d . . . F14A F 0.28847(5) 0.30205(16) 0.37650(9) 0.0413(4) Uani 1 1 d . . . F14B F 0.29337(5) 0.05687(18) 0.41066(9) 0.0455(4) Uani 1 1 d . . . F14C F 0.25199(5) 0.12487(18) 0.30191(8) 0.0433(4) Uani 1 1 d . . . H1 H 0.3951(8) 0.265(3) 0.2872(14) 0.024(7) Uiso 1 1 d . . . H9 H 0.5133(8) 0.092(3) 0.3992(14) 0.029(7) Uiso 1 1 d . . . H10 H 0.5808(10) 0.250(3) 0.4029(15) 0.041(7) Uiso 1 1 d . . . H11 H 0.5715(9) 0.523(3) 0.3816(16) 0.047(8) Uiso 1 1 d . . . H12 H 0.4925(10) 0.626(3) 0.3602(18) 0.064(9) Uiso 1 1 d . . . H13 H 0.4270(8) 0.464(3) 0.3640(14) 0.029(6) Uiso 1 1 d . . . H16 H 0.3429(7) 0.457(2) 0.2583(14) 0.024(6) Uiso 1 1 d . . . H17 H 0.3226(8) 0.615(3) 0.1406(15) 0.036(7) Uiso 1 1 d . . . H18 H 0.2924(8) 0.499(3) 0.0180(16) 0.041(7) Uiso 1 1 d . . . H19 H 0.2770(8) 0.220(3) 0.0130(15) 0.038(7) Uiso 1 1 d . . . H20 H 0.2975(8) 0.068(3) 0.1327(13) 0.025(6) 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 N1 0.0232(10) 0.0239(10) 0.0207(9) 0.0050(8) -0.0013(8) 0.0000(8) C2 0.0258(11) 0.0277(12) 0.0209(11) 0.0022(10) -0.0020(9) 0.0046(10) C3 0.0312(12) 0.0297(13) 0.0253(12) 0.0059(10) 0.0029(10) 0.0066(10) C4 0.0401(14) 0.0230(12) 0.0291(12) 0.0020(10) 0.0081(11) 0.0036(11) C5 0.0291(12) 0.0247(12) 0.0283(12) -0.0006(10) 0.0035(10) -0.0037(10) C6 0.0235(11) 0.0243(11) 0.0217(10) 0.0012(9) 0.0010(9) -0.0008(9) C7 0.0332(13) 0.0410(15) 0.0251(12) 0.0005(11) -0.0013(10) 0.0049(12) C8 0.0266(11) 0.0303(12) 0.0186(10) -0.0018(10) -0.0021(9) 0.0023(10) C9 0.0319(14) 0.0337(14) 0.0342(14) 0.0030(11) -0.0040(10) 0.0088(11) C10 0.0248(13) 0.0512(17) 0.0373(14) -0.0042(12) -0.0053(11) 0.0038(12) C11 0.0309(14) 0.0479(17) 0.0456(15) -0.0081(14) -0.0032(12) -0.0078(13) C12 0.0385(14) 0.0335(14) 0.0633(18) -0.0043(14) -0.0074(14) -0.0007(13) C13 0.0283(13) 0.0320(14) 0.0458(15) -0.0033(12) -0.0065(12) 0.0051(11) C14 0.0276(12) 0.0312(13) 0.0280(12) 0.0039(10) 0.0000(10) -0.0007(10) C15 0.0185(10) 0.0279(12) 0.0236(11) 0.0025(10) 0.0022(9) 0.0025(9) C16 0.0264(12) 0.0282(13) 0.0241(12) -0.0004(10) -0.0012(10) 0.0003(10) C17 0.0291(12) 0.0281(13) 0.0372(14) 0.0060(11) -0.0003(11) 0.0031(11) C18 0.0321(13) 0.0427(15) 0.0281(13) 0.0098(12) -0.0029(11) 0.0040(11) C19 0.0378(14) 0.0465(16) 0.0265(12) -0.0023(12) -0.0089(11) -0.0010(12) C20 0.0304(12) 0.0300(14) 0.0319(13) 0.0000(11) -0.0049(10) -0.0005(11) F3A 0.0479(8) 0.0330(8) 0.0406(8) 0.0095(6) -0.0098(7) 0.0121(7) F3B 0.0340(7) 0.0361(8) 0.0365(7) -0.0060(6) 0.0079(6) 0.0061(6) F4A 0.0490(9) 0.0349(8) 0.0415(8) 0.0130(7) 0.0071(7) -0.0026(7) F4B 0.0558(9) 0.0212(7) 0.0505(8) -0.0035(6) 0.0000(7) 0.0082(7) F5A 0.0423(8) 0.0271(7) 0.0480(8) -0.0025(7) -0.0060(7) -0.0093(6) F5B 0.0436(8) 0.0324(8) 0.0264(7) -0.0038(6) 0.0049(6) 0.0062(6) F7A 0.0422(8) 0.0611(10) 0.0234(6) 0.0028(7) -0.0085(6) 0.0065(7) F7B 0.0583(10) 0.0768(12) 0.0283(7) 0.0008(8) 0.0094(7) -0.0239(9) F7C 0.0607(10) 0.0630(10) 0.0295(8) -0.0108(7) 0.0027(7) 0.0296(8) F14A 0.0395(8) 0.0395(8) 0.0449(8) -0.0088(7) 0.0149(7) 0.0035(7) F14B 0.0439(8) 0.0544(10) 0.0383(8) 0.0191(7) 0.0141(7) 0.0065(7) F14C 0.0245(7) 0.0611(10) 0.0443(8) 0.0008(7) -0.0008(7) -0.0052(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 N1 C6 1.460(3) . ? N1 C2 1.464(3) . ? C2 C8 1.540(3) . ? C2 C3 1.549(3) . ? C2 C7 1.554(3) . ? C3 F3B 1.353(2) . ? C3 F3A 1.354(2) . ? C3 C4 1.531(3) . ? C4 F4A 1.339(3) . ? C4 F4B 1.349(3) . ? C4 C5 1.533(3) . ? C5 F5A 1.351(2) . ? C5 F5B 1.358(2) . ? C5 C6 1.547(3) . ? C6 C15 1.544(3) . ? C6 C14 1.551(3) . ? C7 F7B 1.320(3) . ? C7 F7C 1.321(3) . ? C7 F7A 1.329(3) . ? C8 C13 1.384(3) . ? C8 C9 1.387(3) . ? C9 C10 1.374(3) . ? C10 C11 1.371(4) . ? C11 C12 1.369(4) . ? C12 C13 1.375(4) . ? C14 F14C 1.322(3) . ? C14 F14B 1.325(2) . ? C14 F14A 1.325(3) . ? C15 C20 1.384(3) . ? C15 C16 1.387(3) . ? C16 C17 1.381(3) . ? C17 C18 1.380(3) . ? C18 C19 1.373(4) . ? C19 C20 1.378(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 C6 N1 C2 128.05(18) . . ? N1 C2 C8 106.77(17) . . ? N1 C2 C3 109.38(17) . . ? C8 C2 C3 112.34(17) . . ? N1 C2 C7 112.03(17) . . ? C8 C2 C7 104.92(17) . . ? C3 C2 C7 111.28(18) . . ? F3B C3 F3A 107.18(17) . . ? F3B C3 C4 104.84(17) . . ? F3A C3 C4 107.83(18) . . ? F3B C3 C2 108.18(17) . . ? F3A C3 C2 111.99(18) . . ? C4 C3 C2 116.25(18) . . ? F4A C4 F4B 105.76(17) . . ? F4A C4 C3 111.08(18) . . ? F4B C4 C3 108.36(18) . . ? F4A C4 C5 110.34(18) . . ? F4B C4 C5 107.99(18) . . ? C3 C4 C5 112.99(18) . . ? F5A C5 F5B 107.13(17) . . ? F5A C5 C4 107.74(17) . . ? F5B C5 C4 104.69(17) . . ? F5A C5 C6 112.64(17) . . ? F5B C5 C6 108.14(16) . . ? C4 C5 C6 115.88(18) . . ? N1 C6 C15 107.01(17) . . ? N1 C6 C5 109.67(17) . . ? C15 C6 C5 111.64(17) . . ? N1 C6 C14 111.70(17) . . ? C15 C6 C14 104.68(16) . . ? C5 C6 C14 111.96(17) . . ? F7B C7 F7C 107.60(19) . . ? F7B C7 F7A 105.67(19) . . ? F7C C7 F7A 106.72(19) . . ? F7B C7 C2 114.71(19) . . ? F7C C7 C2 110.27(18) . . ? F7A C7 C2 111.45(18) . . ? C13 C8 C9 118.0(2) . . ? C13 C8 C2 119.2(2) . . ? C9 C8 C2 122.6(2) . . ? C10 C9 C8 120.7(2) . . ? C11 C10 C9 120.7(2) . . ? C12 C11 C10 119.2(3) . . ? C11 C12 C13 120.6(3) . . ? C12 C13 C8 120.8(2) . . ? F14C C14 F14B 106.19(18) . . ? F14C C14 F14A 107.44(18) . . ? F14B C14 F14A 106.79(18) . . ? F14C C14 C6 111.25(17) . . ? F14B C14 C6 114.60(18) . . ? F14A C14 C6 110.21(18) . . ? C20 C15 C16 118.5(2) . . ? C20 C15 C6 122.4(2) . . ? C16 C15 C6 118.96(19) . . ? C17 C16 C15 120.6(2) . . ? C18 C17 C16 120.1(2) . . ? C19 C18 C17 119.5(2) . . ? C18 C19 C20 120.5(2) . . ? C19 C20 C15 120.6(2) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 24.97 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.248 _refine_diff_density_min -0.202 _refine_diff_density_rms 0.044