# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full Chem.Commun. _journal_coden_cambridge 0182 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_email lentz@chemie.fu-berlin.de _publ_contact_author_name 'Dieter Lentz' loop_ _publ_author_name 'Bernd Schmidt' 'Berit Topolinski' 'Phillip Roesch' 'Dieter Lentz' data_pr10 _database_code_depnum_ccdc_archive 'CCDC 876633' #TrackingRef '1a.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C28 H16 F5 N O2' _chemical_formula_weight 493.42 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)/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 16.691(5) _cell_length_b 7.731(2) _cell_length_c 16.655(5) _cell_angle_alpha 90.00 _cell_angle_beta 107.022(6) _cell_angle_gamma 90.00 _cell_volume 2055.0(11) _cell_formula_units_Z 4 _cell_measurement_temperature 133(2) _cell_measurement_reflns_used 978 _cell_measurement_theta_min 2.5 _cell_measurement_theta_max 24.7 _exptl_crystal_description needle _exptl_crystal_colour yellow _exptl_crystal_size_max 0.8 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.595 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1008 _exptl_absorpt_coefficient_mu 0.131 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.803 _exptl_absorpt_correction_T_max 0.862 _exptl_absorpt_process_details 'SADABS (Bruker-AXS)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 133(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'BRUKER-AXS SMART CCD' _diffrn_measurement_method 'omega scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15784 _diffrn_reflns_av_R_equivalents 0.0566 _diffrn_reflns_av_sigmaI/netI 0.0484 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.28 _diffrn_reflns_theta_max 25.04 _reflns_number_total 3602 _reflns_number_gt 2440 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker-AXS)' _computing_cell_refinement 'SAINT (bruker-AXS)' _computing_data_reduction 'SAINT (bruker-AXS)' _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^)+(0.0763P)^2^+0.0000P] 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 3602 _refine_ls_number_parameters 329 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0725 _refine_ls_R_factor_gt 0.0409 _refine_ls_wR_factor_ref 0.1324 _refine_ls_wR_factor_gt 0.1078 _refine_ls_goodness_of_fit_ref 1.038 _refine_ls_restrained_S_all 1.038 _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 0.31767(15) 0.5413(3) 0.32557(16) 0.0167(6) Uani 1 1 d . . . C2 C 0.26445(15) 0.4779(3) 0.24873(16) 0.0157(6) Uani 1 1 d . . . C3 C 0.30065(16) 0.3954(3) 0.19361(16) 0.0188(6) Uani 1 1 d . . . C4 C 0.38932(16) 0.4015(4) 0.21410(17) 0.0235(7) Uani 1 1 d . . . H4 H 0.4144 0.3507 0.1769 0.028 Uiso 1 1 calc R . . C5 C 0.44017(16) 0.4769(4) 0.28491(17) 0.0244(7) Uani 1 1 d . . . H5 H 0.4978 0.4811 0.2937 0.029 Uiso 1 1 calc R . . C6 C 0.40467(16) 0.5483(3) 0.34456(16) 0.0200(6) Uani 1 1 d . . . C7 C 0.44805(15) 0.6289(4) 0.42135(17) 0.0235(7) Uani 1 1 d . . . H7 H 0.5062 0.6375 0.4372 0.028 Uiso 1 1 calc R . . C8 C 0.40452(16) 0.6936(4) 0.47170(17) 0.0228(6) Uani 1 1 d . . . H8 H 0.4346 0.7487 0.5209 0.027 Uiso 1 1 calc R . . C9 C 0.31605(15) 0.6827(3) 0.45428(16) 0.0181(6) Uani 1 1 d . . . C10 C 0.27241(15) 0.5974(3) 0.38109(16) 0.0166(6) Uani 1 1 d . . . C11 C 0.18304(15) 0.5593(3) 0.33685(15) 0.0149(6) Uani 1 1 d . . . C12 C 0.11161(15) 0.5598(3) 0.36555(15) 0.0145(6) Uani 1 1 d . . . C13 C 0.03621(15) 0.5413(3) 0.30256(15) 0.0147(6) Uani 1 1 d . . . C14 C -0.04960(15) 0.5564(3) 0.30993(16) 0.0154(6) Uani 1 1 d . . . C15 C -0.05814(15) 0.5014(3) 0.16932(16) 0.0166(6) Uani 1 1 d . . . C16 C 0.03096(15) 0.5166(3) 0.21845(15) 0.0151(6) Uani 1 1 d . . . C17 C 0.10093(15) 0.5009(3) 0.18958(16) 0.0157(6) Uani 1 1 d . . . C18 C 0.17801(15) 0.5064(3) 0.25310(16) 0.0152(6) Uani 1 1 d . . . C19 C 0.25556(16) 0.2917(4) 0.11796(16) 0.0225(6) Uani 1 1 d . . . H19A H 0.2064 0.2404 0.1268 0.034 Uiso 1 1 calc R . . H19B H 0.2919 0.2022 0.1089 0.034 Uiso 1 1 calc R . . H19C H 0.2395 0.3658 0.0697 0.034 Uiso 1 1 calc R . . C20 C 0.27822(17) 0.7754(4) 0.51369(17) 0.0253(7) Uani 1 1 d . . . H20A H 0.2248 0.8224 0.4830 0.038 Uiso 1 1 calc R . . H20B H 0.3147 0.8675 0.5409 0.038 Uiso 1 1 calc R . . H20C H 0.2709 0.6956 0.5552 0.038 Uiso 1 1 calc R . . C21 C 0.11337(16) 0.5597(4) 0.45603(15) 0.0202(6) Uani 1 1 d . . . H21A H 0.1033 0.6748 0.4725 0.030 Uiso 1 1 calc R . . H21B H 0.1672 0.5209 0.4901 0.030 Uiso 1 1 calc R . . H21C H 0.0707 0.4835 0.4635 0.030 Uiso 1 1 calc R . . C22 C 0.09193(16) 0.5020(4) 0.09724(15) 0.0196(6) Uani 1 1 d . . . H22A H 0.1433 0.5408 0.0884 0.029 Uiso 1 1 calc R . . H22B H 0.0473 0.5786 0.0691 0.029 Uiso 1 1 calc R . . H22C H 0.0795 0.3872 0.0751 0.029 Uiso 1 1 calc R . . C23 C -0.19249(15) 0.5328(3) 0.20580(16) 0.0157(6) Uani 1 1 d . . . C24 C -0.23609(15) 0.4478(3) 0.25323(16) 0.0169(6) Uani 1 1 d . . . C25 C -0.32199(16) 0.4538(3) 0.23263(17) 0.0207(6) Uani 1 1 d . . . C26 C -0.36738(15) 0.5401(4) 0.16208(17) 0.0220(6) Uani 1 1 d . . . C27 C -0.32619(16) 0.6227(3) 0.11286(16) 0.0209(6) Uani 1 1 d . . . C28 C -0.24015(15) 0.6220(3) 0.13566(16) 0.0179(6) Uani 1 1 d . . . F1 F -0.19528(8) 0.35424(19) 0.32040(9) 0.0217(4) Uani 1 1 d . . . F2 F -0.36156(9) 0.3745(2) 0.28198(10) 0.0284(4) Uani 1 1 d . . . F3 F -0.45115(9) 0.5433(2) 0.14105(10) 0.0323(4) Uani 1 1 d . . . F4 F -0.36961(9) 0.7053(2) 0.04295(9) 0.0304(4) Uani 1 1 d . . . F5 F -0.20277(9) 0.71333(19) 0.08866(9) 0.0226(4) Uani 1 1 d . . . N1 N -0.10420(12) 0.5294(3) 0.22757(12) 0.0164(5) Uani 1 1 d . . . O1 O -0.07356(10) 0.5910(2) 0.36979(11) 0.0198(4) Uani 1 1 d . . . O2 O -0.08969(10) 0.4669(2) 0.09610(11) 0.0199(4) 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 0.0144(13) 0.0166(14) 0.0184(14) 0.0020(11) 0.0037(11) 0.0005(11) C2 0.0156(13) 0.0146(14) 0.0176(14) 0.0043(11) 0.0061(11) 0.0004(11) C3 0.0229(14) 0.0162(14) 0.0198(14) 0.0055(12) 0.0105(12) 0.0018(11) C4 0.0197(14) 0.0250(16) 0.0297(16) 0.0000(13) 0.0133(13) 0.0005(12) C5 0.0131(13) 0.0301(17) 0.0313(17) 0.0019(14) 0.0087(12) 0.0017(12) C6 0.0175(14) 0.0189(15) 0.0236(15) 0.0041(12) 0.0058(12) -0.0007(11) C7 0.0117(13) 0.0272(16) 0.0286(16) 0.0039(13) 0.0015(12) -0.0016(12) C8 0.0196(14) 0.0241(16) 0.0212(15) -0.0007(13) 0.0003(12) -0.0007(12) C9 0.0185(13) 0.0172(15) 0.0167(14) 0.0033(11) 0.0022(11) 0.0014(11) C10 0.0161(13) 0.0144(14) 0.0183(14) 0.0032(11) 0.0036(11) 0.0010(11) C11 0.0158(13) 0.0132(14) 0.0140(13) 0.0006(11) 0.0019(11) 0.0008(11) C12 0.0170(13) 0.0131(14) 0.0129(13) 0.0024(11) 0.0037(11) 0.0022(10) C13 0.0158(13) 0.0129(14) 0.0159(13) 0.0008(11) 0.0056(11) 0.0009(11) C14 0.0167(13) 0.0139(14) 0.0155(14) 0.0012(11) 0.0048(11) 0.0013(11) C15 0.0157(13) 0.0165(14) 0.0184(15) 0.0004(12) 0.0062(11) 0.0002(11) C16 0.0185(13) 0.0133(14) 0.0133(13) -0.0010(11) 0.0043(11) -0.0018(11) C17 0.0176(13) 0.0147(14) 0.0154(13) -0.0003(11) 0.0057(11) -0.0021(11) C18 0.0158(13) 0.0135(14) 0.0181(14) 0.0011(11) 0.0079(11) -0.0014(10) C19 0.0227(14) 0.0261(16) 0.0218(15) -0.0022(13) 0.0113(12) 0.0011(12) C20 0.0245(15) 0.0268(16) 0.0214(15) -0.0039(13) 0.0017(12) 0.0002(12) C21 0.0170(13) 0.0274(16) 0.0169(14) 0.0000(12) 0.0063(11) 0.0006(12) C22 0.0169(13) 0.0251(16) 0.0188(14) 0.0005(12) 0.0082(11) -0.0017(11) C23 0.0125(12) 0.0164(14) 0.0190(14) -0.0036(11) 0.0059(11) 0.0004(11) C24 0.0206(14) 0.0143(14) 0.0153(14) -0.0026(12) 0.0043(11) 0.0013(11) C25 0.0203(14) 0.0227(15) 0.0236(15) -0.0021(13) 0.0136(12) -0.0021(12) C26 0.0131(13) 0.0245(16) 0.0284(16) -0.0076(13) 0.0061(12) 0.0010(12) C27 0.0192(14) 0.0210(15) 0.0190(15) -0.0032(12) 0.0000(12) 0.0033(12) C28 0.0186(14) 0.0183(15) 0.0175(14) -0.0013(12) 0.0063(11) -0.0021(11) F1 0.0214(8) 0.0234(9) 0.0215(8) 0.0044(7) 0.0079(7) 0.0021(7) F2 0.0210(8) 0.0341(10) 0.0358(10) 0.0010(8) 0.0170(7) -0.0025(7) F3 0.0115(8) 0.0437(11) 0.0402(10) -0.0016(8) 0.0052(7) 0.0022(7) F4 0.0241(9) 0.0357(10) 0.0240(9) 0.0038(8) -0.0043(7) 0.0074(7) F5 0.0253(8) 0.0216(9) 0.0221(8) 0.0026(7) 0.0089(7) -0.0011(7) N1 0.0123(11) 0.0220(13) 0.0151(11) -0.0013(10) 0.0042(9) 0.0000(9) O1 0.0171(9) 0.0252(11) 0.0188(10) -0.0026(8) 0.0081(8) 0.0015(8) O2 0.0175(9) 0.0249(11) 0.0163(10) -0.0028(8) 0.0032(8) -0.0038(8) _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 C6 1.394(3) . ? C1 C2 1.415(4) . ? C1 C10 1.422(3) . ? C2 C3 1.393(4) . ? C2 C18 1.482(3) . ? C3 C4 1.419(4) . ? C3 C19 1.498(4) . ? C4 C5 1.366(4) . ? C4 H4 0.9300 . ? C5 C6 1.410(4) . ? C5 H5 0.9300 . ? C6 C7 1.416(4) . ? C7 C8 1.356(4) . ? C7 H7 0.9300 . ? C8 C9 1.422(4) . ? C8 H8 0.9300 . ? C9 C10 1.390(4) . ? C9 C20 1.503(4) . ? C10 C11 1.487(3) . ? C11 C12 1.408(3) . ? C11 C18 1.432(3) . ? C12 C13 1.390(3) . ? C12 C21 1.499(3) . ? C13 C16 1.391(3) . ? C13 C14 1.477(3) . ? C14 O1 1.208(3) . ? C14 N1 1.423(3) . ? C15 O2 1.208(3) . ? C15 N1 1.420(3) . ? C15 C16 1.477(3) . ? C16 C17 1.392(3) . ? C17 C18 1.407(4) . ? C17 C22 1.501(3) . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? C20 H20A 0.9600 . ? C20 H20B 0.9600 . ? C20 H20C 0.9600 . ? C21 H21A 0.9600 . ? C21 H21B 0.9600 . ? C21 H21C 0.9600 . ? C22 H22A 0.9600 . ? C22 H22B 0.9600 . ? C22 H22C 0.9600 . ? C23 C24 1.387(4) . ? C23 C28 1.389(4) . ? C23 N1 1.411(3) . ? C24 F1 1.339(3) . ? C24 C25 1.374(4) . ? C25 F2 1.344(3) . ? C25 C26 1.371(4) . ? C26 F3 1.339(3) . ? C26 C27 1.372(4) . ? C27 F4 1.340(3) . ? C27 C28 1.374(3) . ? C28 F5 1.336(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 C1 C2 123.7(2) . . ? C6 C1 C10 123.8(2) . . ? C2 C1 C10 112.4(2) . . ? C3 C2 C1 118.4(2) . . ? C3 C2 C18 135.8(2) . . ? C1 C2 C18 105.5(2) . . ? C2 C3 C4 116.7(2) . . ? C2 C3 C19 126.3(2) . . ? C4 C3 C19 116.9(2) . . ? C5 C4 C3 124.2(3) . . ? C5 C4 H4 117.9 . . ? C3 C4 H4 117.9 . . ? C4 C5 C6 119.5(2) . . ? C4 C5 H5 120.2 . . ? C6 C5 H5 120.2 . . ? C1 C6 C5 116.7(2) . . ? C1 C6 C7 116.4(2) . . ? C5 C6 C7 126.8(2) . . ? C8 C7 C6 119.7(2) . . ? C8 C7 H7 120.1 . . ? C6 C7 H7 120.1 . . ? C7 C8 C9 124.4(3) . . ? C7 C8 H8 117.8 . . ? C9 C8 H8 117.8 . . ? C10 C9 C8 117.0(2) . . ? C10 C9 C20 126.2(2) . . ? C8 C9 C20 116.7(2) . . ? C9 C10 C1 118.2(2) . . ? C9 C10 C11 136.1(2) . . ? C1 C10 C11 105.3(2) . . ? C12 C11 C18 121.2(2) . . ? C12 C11 C10 131.1(2) . . ? C18 C11 C10 107.7(2) . . ? C13 C12 C11 114.4(2) . . ? C13 C12 C21 120.4(2) . . ? C11 C12 C21 124.9(2) . . ? C16 C13 C12 123.4(2) . . ? C16 C13 C14 108.5(2) . . ? C12 C13 C14 127.9(2) . . ? O1 C14 N1 123.7(2) . . ? O1 C14 C13 130.5(2) . . ? N1 C14 C13 105.7(2) . . ? O2 C15 N1 124.1(2) . . ? O2 C15 C16 130.3(2) . . ? N1 C15 C16 105.5(2) . . ? C13 C16 C17 123.2(2) . . ? C13 C16 C15 109.0(2) . . ? C17 C16 C15 127.7(2) . . ? C16 C17 C18 114.4(2) . . ? C16 C17 C22 120.7(2) . . ? C18 C17 C22 124.4(2) . . ? C17 C18 C11 121.4(2) . . ? C17 C18 C2 130.4(2) . . ? C11 C18 C2 108.0(2) . . ? C3 C19 H19A 109.5 . . ? C3 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C3 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C9 C20 H20A 109.5 . . ? C9 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C9 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C12 C21 H21A 109.5 . . ? C12 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C12 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C17 C22 H22A 109.5 . . ? C17 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C17 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C24 C23 C28 116.6(2) . . ? C24 C23 N1 121.8(2) . . ? C28 C23 N1 121.6(2) . . ? F1 C24 C25 117.7(2) . . ? F1 C24 C23 120.6(2) . . ? C25 C24 C23 121.7(2) . . ? F2 C25 C26 120.0(2) . . ? F2 C25 C24 119.7(2) . . ? C26 C25 C24 120.3(2) . . ? F3 C26 C27 120.2(2) . . ? F3 C26 C25 120.4(2) . . ? C27 C26 C25 119.4(2) . . ? F4 C27 C26 120.2(2) . . ? F4 C27 C28 119.9(2) . . ? C26 C27 C28 119.9(2) . . ? F5 C28 C27 117.7(2) . . ? F5 C28 C23 120.3(2) . . ? C27 C28 C23 122.0(2) . . ? C23 N1 C15 124.1(2) . . ? C23 N1 C14 124.8(2) . . ? C15 N1 C14 111.04(19) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 9.5(4) . . . . ? C10 C1 C2 C3 -170.7(2) . . . . ? C6 C1 C2 C18 -175.9(2) . . . . ? C10 C1 C2 C18 4.0(3) . . . . ? C1 C2 C3 C4 -8.1(4) . . . . ? C18 C2 C3 C4 179.4(3) . . . . ? C1 C2 C3 C19 167.7(2) . . . . ? C18 C2 C3 C19 -4.8(5) . . . . ? C2 C3 C4 C5 2.3(4) . . . . ? C19 C3 C4 C5 -173.9(3) . . . . ? C3 C4 C5 C6 2.8(4) . . . . ? C2 C1 C6 C5 -4.3(4) . . . . ? C10 C1 C6 C5 175.9(3) . . . . ? C2 C1 C6 C7 174.8(3) . . . . ? C10 C1 C6 C7 -5.0(4) . . . . ? C4 C5 C6 C1 -1.8(4) . . . . ? C4 C5 C6 C7 179.2(3) . . . . ? C1 C6 C7 C8 0.1(4) . . . . ? C5 C6 C7 C8 179.1(3) . . . . ? C6 C7 C8 C9 1.8(4) . . . . ? C7 C8 C9 C10 1.0(4) . . . . ? C7 C8 C9 C20 -174.8(3) . . . . ? C8 C9 C10 C1 -5.5(4) . . . . ? C20 C9 C10 C1 169.9(3) . . . . ? C8 C9 C10 C11 -177.8(3) . . . . ? C20 C9 C10 C11 -2.4(5) . . . . ? C6 C1 C10 C9 7.9(4) . . . . ? C2 C1 C10 C9 -172.0(2) . . . . ? C6 C1 C10 C11 -177.6(2) . . . . ? C2 C1 C10 C11 2.5(3) . . . . ? C9 C10 C11 C12 -18.9(5) . . . . ? C1 C10 C11 C12 168.2(3) . . . . ? C9 C10 C11 C18 164.7(3) . . . . ? C1 C10 C11 C18 -8.2(3) . . . . ? C18 C11 C12 C13 -12.8(3) . . . . ? C10 C11 C12 C13 171.2(2) . . . . ? C18 C11 C12 C21 160.5(2) . . . . ? C10 C11 C12 C21 -15.5(4) . . . . ? C11 C12 C13 C16 2.7(4) . . . . ? C21 C12 C13 C16 -170.9(2) . . . . ? C11 C12 C13 C14 -172.4(2) . . . . ? C21 C12 C13 C14 14.0(4) . . . . ? C16 C13 C14 O1 -173.9(3) . . . . ? C12 C13 C14 O1 1.8(5) . . . . ? C16 C13 C14 N1 3.3(3) . . . . ? C12 C13 C14 N1 179.0(2) . . . . ? C12 C13 C16 C17 2.7(4) . . . . ? C14 C13 C16 C17 178.6(2) . . . . ? C12 C13 C16 C15 179.7(2) . . . . ? C14 C13 C16 C15 -4.3(3) . . . . ? O2 C15 C16 C13 -173.9(3) . . . . ? N1 C15 C16 C13 3.7(3) . . . . ? O2 C15 C16 C17 3.0(5) . . . . ? N1 C15 C16 C17 -179.5(2) . . . . ? C13 C16 C17 C18 2.0(4) . . . . ? C15 C16 C17 C18 -174.5(2) . . . . ? C13 C16 C17 C22 -170.5(2) . . . . ? C15 C16 C17 C22 13.0(4) . . . . ? C16 C17 C18 C11 -12.2(4) . . . . ? C22 C17 C18 C11 160.0(2) . . . . ? C16 C17 C18 C2 173.5(2) . . . . ? C22 C17 C18 C2 -14.3(4) . . . . ? C12 C11 C18 C17 18.5(4) . . . . ? C10 C11 C18 C17 -164.7(2) . . . . ? C12 C11 C18 C2 -166.1(2) . . . . ? C10 C11 C18 C2 10.8(3) . . . . ? C3 C2 C18 C17 -21.0(5) . . . . ? C1 C2 C18 C17 165.8(3) . . . . ? C3 C2 C18 C11 164.1(3) . . . . ? C1 C2 C18 C11 -9.1(3) . . . . ? C28 C23 C24 F1 177.9(2) . . . . ? N1 C23 C24 F1 -2.2(4) . . . . ? C28 C23 C24 C25 -1.0(4) . . . . ? N1 C23 C24 C25 178.9(2) . . . . ? F1 C24 C25 F2 3.3(4) . . . . ? C23 C24 C25 F2 -177.7(2) . . . . ? F1 C24 C25 C26 -176.6(2) . . . . ? C23 C24 C25 C26 2.4(4) . . . . ? F2 C25 C26 F3 -1.2(4) . . . . ? C24 C25 C26 F3 178.7(2) . . . . ? F2 C25 C26 C27 179.1(2) . . . . ? C24 C25 C26 C27 -1.0(4) . . . . ? F3 C26 C27 F4 -0.8(4) . . . . ? C25 C26 C27 F4 178.9(2) . . . . ? F3 C26 C27 C28 178.6(2) . . . . ? C25 C26 C27 C28 -1.6(4) . . . . ? F4 C27 C28 F5 3.6(4) . . . . ? C26 C27 C28 F5 -175.9(2) . . . . ? F4 C27 C28 C23 -177.5(2) . . . . ? C26 C27 C28 C23 3.0(4) . . . . ? C24 C23 C28 F5 177.2(2) . . . . ? N1 C23 C28 F5 -2.7(4) . . . . ? C24 C23 C28 C27 -1.7(4) . . . . ? N1 C23 C28 C27 178.4(2) . . . . ? C24 C23 N1 C15 135.4(3) . . . . ? C28 C23 N1 C15 -44.7(4) . . . . ? C24 C23 N1 C14 -45.8(4) . . . . ? C28 C23 N1 C14 134.1(3) . . . . ? O2 C15 N1 C23 -4.8(4) . . . . ? C16 C15 N1 C23 177.4(2) . . . . ? O2 C15 N1 C14 176.2(2) . . . . ? C16 C15 N1 C14 -1.6(3) . . . . ? O1 C14 N1 C23 -2.5(4) . . . . ? C13 C14 N1 C23 -179.9(2) . . . . ? O1 C14 N1 C15 176.4(2) . . . . ? C13 C14 N1 C15 -1.0(3) . . . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 25.04 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.261 _refine_diff_density_min -0.259 _refine_diff_density_rms 0.063 # Attachment '2.CIF' data_pr16b _database_code_depnum_ccdc_archive 'CCDC 876634' #TrackingRef '2.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C38 H20 F10 N2 O4' _chemical_formula_weight 758.56 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 Cc 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 12.407(4) _cell_length_b 27.476(8) _cell_length_c 9.607(3) _cell_angle_alpha 90.00 _cell_angle_beta 110.687(6) _cell_angle_gamma 90.00 _cell_volume 3063.9(15) _cell_formula_units_Z 4 _cell_measurement_temperature 133(2) _cell_measurement_reflns_used 1002 _cell_measurement_theta_min 2.7 _cell_measurement_theta_max 29.8 _exptl_crystal_description needle _exptl_crystal_colour yellow _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.644 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1536 _exptl_absorpt_coefficient_mu 0.148 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.785 _exptl_absorpt_correction_T_max 0.862 _exptl_absorpt_process_details 'SADABS (BRUKER-AXS)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 133(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 'SMART CCD Bruker-AXS' _diffrn_measurement_method 'omega scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 17831 _diffrn_reflns_av_R_equivalents 0.0565 _diffrn_reflns_av_sigmaI/netI 0.0425 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -34 _diffrn_reflns_limit_k_max 34 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 1.90 _diffrn_reflns_theta_max 26.48 _reflns_number_total 3125 _reflns_number_gt 2420 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker-AXS)' _computing_cell_refinement 'SAINT (Bruker-AXS)' _computing_data_reduction 'SAINT (Bruker-AXS)' _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^)+(0.0775P)^2^+0.0000P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.3(8) _refine_ls_number_reflns 3125 _refine_ls_number_parameters 491 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0648 _refine_ls_R_factor_gt 0.0463 _refine_ls_wR_factor_ref 0.1235 _refine_ls_wR_factor_gt 0.1139 _refine_ls_goodness_of_fit_ref 1.061 _refine_ls_restrained_S_all 1.061 _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 0.4079(4) 0.95207(16) 0.9083(6) 0.0233(10) Uani 1 1 d . . . C2 C 0.4820(4) 0.92568(15) 1.0312(5) 0.0207(9) Uani 1 1 d . . . C3 C 0.5490(4) 0.95194(18) 1.1557(5) 0.0279(11) Uani 1 1 d . . . C4 C 0.5389(5) 1.00383(19) 1.1489(6) 0.0356(12) Uani 1 1 d . . . H4 H 0.5844 1.0221 1.2331 0.043 Uiso 1 1 calc R . . C5 C 0.4677(5) 1.02861(17) 1.0282(6) 0.0356(12) Uani 1 1 d . . . H5 H 0.4651 1.0632 1.0294 0.043 Uiso 1 1 calc R . . C6 C 0.3980(4) 1.00273(17) 0.9018(6) 0.0288(11) Uani 1 1 d . . . C7 C 0.3178(5) 1.02329(18) 0.7726(6) 0.0360(12) Uani 1 1 d . . . H7 H 0.3081 1.0576 0.7635 0.043 Uiso 1 1 calc R . . C8 C 0.2550(5) 0.99363(18) 0.6615(6) 0.0339(12) Uani 1 1 d . . . H8 H 0.2019 1.0084 0.5751 0.041 Uiso 1 1 calc R . . C9 C 0.2620(4) 0.94249(17) 0.6641(5) 0.0268(10) Uani 1 1 d . . . C10 C 0.3425(4) 0.92105(16) 0.7907(5) 0.0213(10) Uani 1 1 d . . . C11 C 0.3827(4) 0.87140(16) 0.8445(5) 0.0196(9) Uani 1 1 d . . . C12 C 0.4627(4) 0.87384(15) 0.9859(5) 0.0206(10) Uani 1 1 d . . . C13 C 0.5086(4) 0.82524(15) 1.0588(5) 0.0220(10) Uani 1 1 d . . . C14 C 0.5614(4) 0.79775(16) 0.9559(6) 0.0241(10) Uani 1 1 d . . . H14 H 0.5760 0.7631 0.9894 0.029 Uiso 1 1 calc R . . C15 C 0.4777(4) 0.79890(16) 0.7953(5) 0.0233(10) Uani 1 1 d . . . H15 H 0.4665 0.7650 0.7547 0.028 Uiso 1 1 calc R . . C16 C 0.3582(4) 0.82079(15) 0.7799(5) 0.0212(10) Uani 1 1 d . . . C17 C 0.3165(4) 0.78962(16) 0.8878(6) 0.0240(10) Uani 1 1 d . . . H17 H 0.3101 0.7546 0.8572 0.029 Uiso 1 1 calc R . . C18 C 0.3995(4) 0.79480(16) 1.0489(5) 0.0244(10) Uani 1 1 d . . . H18 H 0.4240 0.7617 1.0919 0.029 Uiso 1 1 calc R . . C19 C 0.3321(4) 0.81892(19) 1.1309(6) 0.0297(11) Uani 1 1 d . . . C20 C 0.2012(4) 0.80779(15) 0.8890(6) 0.0241(10) Uani 1 1 d . . . C21 C 0.6721(4) 0.82000(16) 0.9537(5) 0.0233(10) Uani 1 1 d . . . C22 C 0.5376(4) 0.82886(16) 0.7115(5) 0.0247(10) Uani 1 1 d . . . C23 C 0.6343(5) 0.9333(2) 1.2986(6) 0.0432(14) Uani 1 1 d . . . H23A H 0.6980 0.9173 1.2788 0.065 Uiso 1 1 calc R . . H23B H 0.5965 0.9099 1.3432 0.065 Uiso 1 1 calc R . . H23C H 0.6643 0.9606 1.3672 0.065 Uiso 1 1 calc R . . C24 C 0.1812(5) 0.9167(2) 0.5288(6) 0.0399(14) Uani 1 1 d . . . H24A H 0.1402 0.8909 0.5603 0.060 Uiso 1 1 calc R . . H24B H 0.2254 0.9024 0.4723 0.060 Uiso 1 1 calc R . . H24C H 0.1253 0.9401 0.4660 0.060 Uiso 1 1 calc R . . C25 C 0.2759(4) 0.81185(17) 0.6176(6) 0.0307(12) Uani 1 1 d . . . H25A H 0.3035 0.8300 0.5490 0.046 Uiso 1 1 calc R . . H25B H 0.1982 0.8229 0.6066 0.046 Uiso 1 1 calc R . . H25C H 0.2740 0.7770 0.5950 0.046 Uiso 1 1 calc R . . C26 C 0.5940(4) 0.82265(19) 1.2183(6) 0.0323(12) Uani 1 1 d . . . H26A H 0.5586 0.8364 1.2860 0.048 Uiso 1 1 calc R . . H26B H 0.6633 0.8413 1.2263 0.048 Uiso 1 1 calc R . . H26C H 0.6150 0.7886 1.2450 0.048 Uiso 1 1 calc R . . C27 C 0.1332(4) 0.84524(16) 1.0791(6) 0.0242(10) Uani 1 1 d . . . C28 C 0.0884(4) 0.89087(17) 1.0332(6) 0.0252(10) Uani 1 1 d . . . C29 C 0.0144(4) 0.91283(17) 1.0924(6) 0.0275(11) Uani 1 1 d . . . C30 C -0.0195(4) 0.88818(17) 1.1942(5) 0.0268(11) Uani 1 1 d . . . C31 C 0.0239(4) 0.84276(17) 1.2417(6) 0.0262(10) Uani 1 1 d . . . C32 C 0.0997(4) 0.82176(16) 1.1846(6) 0.0240(10) Uani 1 1 d . . . C33 C 0.7303(4) 0.86319(16) 0.7615(5) 0.0241(10) Uani 1 1 d . . . C34 C 0.7612(4) 0.91100(17) 0.8053(5) 0.0273(11) Uani 1 1 d . . . C35 C 0.8252(4) 0.93712(17) 0.7412(6) 0.0339(12) Uani 1 1 d . . . C36 C 0.8655(5) 0.9157(2) 0.6410(6) 0.0367(12) Uani 1 1 d . . . C37 C 0.8402(4) 0.8679(2) 0.6018(6) 0.0342(12) Uani 1 1 d . . . C38 C 0.7714(4) 0.84236(18) 0.6613(6) 0.0321(12) Uani 1 1 d . . . F1 F 0.1194(2) 0.91470(10) 0.9315(3) 0.0350(7) Uani 1 1 d . . . F2 F -0.0239(3) 0.95770(10) 1.0518(3) 0.0384(7) Uani 1 1 d . . . F3 F -0.0908(2) 0.90928(11) 1.2515(3) 0.0372(7) Uani 1 1 d . . . F4 F -0.0067(2) 0.81884(10) 1.3430(3) 0.0348(7) Uani 1 1 d . . . F5 F 0.1439(3) 0.77780(9) 1.2352(3) 0.0365(7) Uani 1 1 d . . . F6 F 0.7240(2) 0.93154(10) 0.9056(3) 0.0330(7) Uani 1 1 d . . . F7 F 0.7428(3) 0.79620(10) 0.6160(4) 0.0418(8) Uani 1 1 d . . . F8 F 0.8790(3) 0.84689(13) 0.5041(4) 0.0549(10) Uani 1 1 d . . . F9 F 0.9302(3) 0.94096(13) 0.5814(4) 0.0538(9) Uani 1 1 d . . . F10 F 0.8485(3) 0.98456(10) 0.7759(4) 0.0465(8) Uani 1 1 d . . . N1 N 0.2186(3) 0.82454(13) 1.0308(4) 0.0253(9) Uani 1 1 d . . . N2 N 0.6501(3) 0.83798(14) 0.8098(4) 0.0245(9) Uani 1 1 d . . . O1 O 0.3623(3) 0.83198(17) 1.2585(4) 0.0480(11) Uani 1 1 d . . . O2 O 0.1090(3) 0.80750(13) 0.7895(4) 0.0372(9) Uani 1 1 d . . . O3 O 0.7636(3) 0.82280(13) 1.0516(4) 0.0359(9) Uani 1 1 d . . . O4 O 0.5037(3) 0.84273(14) 0.5857(4) 0.0366(9) 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 0.026(3) 0.019(2) 0.032(2) 0.0012(18) 0.019(2) 0.0011(17) C2 0.019(2) 0.024(2) 0.022(2) -0.0049(18) 0.0105(18) -0.0041(17) C3 0.024(2) 0.035(3) 0.028(3) -0.007(2) 0.013(2) -0.0036(19) C4 0.039(3) 0.036(3) 0.041(3) -0.013(2) 0.026(3) -0.013(2) C5 0.042(3) 0.023(2) 0.048(3) -0.003(2) 0.024(3) -0.006(2) C6 0.035(3) 0.023(2) 0.037(3) -0.002(2) 0.024(2) -0.004(2) C7 0.043(3) 0.022(2) 0.049(3) 0.004(2) 0.024(3) 0.004(2) C8 0.033(3) 0.034(3) 0.039(3) 0.014(2) 0.019(2) 0.012(2) C9 0.022(2) 0.033(2) 0.029(3) 0.006(2) 0.013(2) 0.0061(19) C10 0.018(2) 0.022(2) 0.028(3) 0.0045(18) 0.0133(19) 0.0027(17) C11 0.015(2) 0.023(2) 0.024(3) 0.0005(18) 0.0113(19) -0.0014(16) C12 0.018(2) 0.025(2) 0.022(2) 0.0031(18) 0.0120(19) 0.0006(17) C13 0.021(2) 0.022(2) 0.023(3) 0.0022(18) 0.008(2) 0.0000(17) C14 0.018(2) 0.022(2) 0.035(3) 0.0038(18) 0.013(2) 0.0010(17) C15 0.022(2) 0.020(2) 0.032(3) -0.0056(19) 0.014(2) -0.0008(17) C16 0.015(2) 0.019(2) 0.032(3) -0.0016(19) 0.011(2) -0.0044(16) C17 0.024(2) 0.019(2) 0.035(3) -0.0003(19) 0.018(2) -0.0032(18) C18 0.022(2) 0.025(2) 0.030(3) 0.006(2) 0.012(2) 0.0041(18) C19 0.020(2) 0.039(3) 0.033(3) 0.009(2) 0.015(2) 0.001(2) C20 0.020(2) 0.021(2) 0.032(3) -0.0036(19) 0.011(2) -0.0054(18) C21 0.018(2) 0.024(2) 0.032(3) -0.0016(19) 0.013(2) 0.0032(17) C22 0.023(2) 0.028(2) 0.026(3) -0.004(2) 0.013(2) 0.0006(19) C23 0.038(3) 0.049(3) 0.035(3) -0.013(3) 0.003(3) -0.002(2) C24 0.039(3) 0.039(3) 0.032(3) 0.004(2) 0.000(2) 0.001(2) C25 0.028(3) 0.027(2) 0.035(3) -0.010(2) 0.009(2) -0.0022(19) C26 0.027(3) 0.041(3) 0.030(3) 0.009(2) 0.010(2) 0.002(2) C27 0.019(2) 0.023(2) 0.035(3) -0.003(2) 0.015(2) -0.0023(18) C28 0.019(2) 0.027(2) 0.031(3) -0.001(2) 0.010(2) -0.0032(18) C29 0.021(2) 0.025(2) 0.032(3) -0.005(2) 0.005(2) 0.0022(18) C30 0.019(2) 0.031(3) 0.032(3) -0.006(2) 0.012(2) -0.0004(18) C31 0.024(2) 0.027(2) 0.031(3) -0.0017(19) 0.015(2) -0.0046(18) C32 0.024(2) 0.019(2) 0.034(3) -0.0010(19) 0.015(2) 0.0021(17) C33 0.019(2) 0.027(2) 0.032(3) 0.001(2) 0.015(2) 0.0001(18) C34 0.023(2) 0.031(3) 0.028(3) 0.006(2) 0.009(2) 0.0022(19) C35 0.029(3) 0.026(2) 0.039(3) 0.004(2) 0.003(2) -0.004(2) C36 0.033(3) 0.043(3) 0.040(3) 0.011(2) 0.021(3) -0.004(2) C37 0.034(3) 0.042(3) 0.034(3) 0.002(2) 0.022(2) 0.003(2) C38 0.030(3) 0.032(3) 0.041(3) 0.006(2) 0.020(2) 0.001(2) F1 0.0367(16) 0.0301(15) 0.0414(18) 0.0032(13) 0.0177(14) -0.0029(12) F2 0.0387(17) 0.0264(14) 0.0470(19) 0.0028(13) 0.0115(14) 0.0091(12) F3 0.0336(16) 0.0409(17) 0.0440(18) -0.0071(13) 0.0222(14) 0.0100(13) F4 0.0347(17) 0.0380(16) 0.0429(19) 0.0029(13) 0.0274(14) 0.0023(12) F5 0.0391(16) 0.0236(14) 0.059(2) 0.0061(13) 0.0316(15) 0.0045(12) F6 0.0379(16) 0.0295(14) 0.0334(17) -0.0025(12) 0.0146(14) 0.0027(12) F7 0.054(2) 0.0312(15) 0.055(2) -0.0072(14) 0.0372(17) -0.0055(14) F8 0.070(3) 0.057(2) 0.064(2) -0.0005(17) 0.056(2) -0.0007(17) F9 0.056(2) 0.057(2) 0.063(2) 0.0140(18) 0.0380(19) -0.0136(17) F10 0.055(2) 0.0284(15) 0.053(2) 0.0063(14) 0.0155(16) -0.0097(14) N1 0.0158(19) 0.026(2) 0.038(3) 0.0019(17) 0.0132(18) 0.0013(15) N2 0.025(2) 0.027(2) 0.028(2) 0.0027(16) 0.0178(18) -0.0023(16) O1 0.030(2) 0.086(3) 0.030(2) 0.000(2) 0.0138(18) 0.0104(19) O2 0.0188(18) 0.048(2) 0.047(2) -0.0125(17) 0.0137(18) -0.0046(15) O3 0.0212(19) 0.050(2) 0.035(2) 0.0088(16) 0.0080(16) -0.0022(15) O4 0.031(2) 0.054(2) 0.026(2) -0.0002(16) 0.0108(17) -0.0058(17) _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 C6 1.397(6) . ? C1 C2 1.414(6) . ? C1 C10 1.419(7) . ? C2 C3 1.393(6) . ? C2 C12 1.484(6) . ? C3 C4 1.431(7) . ? C3 C23 1.497(7) . ? C4 C5 1.366(8) . ? C5 C6 1.409(7) . ? C6 C7 1.406(8) . ? C7 C8 1.350(8) . ? C8 C9 1.407(7) . ? C9 C10 1.402(6) . ? C9 C24 1.508(7) . ? C10 C11 1.481(6) . ? C11 C12 1.372(6) . ? C11 C16 1.510(6) . ? C12 C13 1.521(6) . ? C13 C26 1.526(7) . ? C13 C14 1.560(7) . ? C13 C18 1.565(6) . ? C14 C21 1.511(6) . ? C14 C15 1.526(7) . ? C15 C22 1.517(7) . ? C15 C16 1.557(6) . ? C16 C25 1.552(7) . ? C16 C17 1.567(7) . ? C17 C20 1.519(6) . ? C17 C18 1.533(7) . ? C18 C19 1.491(7) . ? C19 O1 1.204(7) . ? C19 N1 1.405(6) . ? C20 O2 1.204(6) . ? C20 N1 1.381(6) . ? C21 O3 1.194(5) . ? C21 N2 1.401(6) . ? C22 O4 1.193(6) . ? C22 N2 1.404(6) . ? C27 C28 1.379(6) . ? C27 C32 1.383(7) . ? C27 N1 1.417(6) . ? C28 F1 1.340(6) . ? C28 C29 1.379(7) . ? C29 F2 1.329(5) . ? C29 C30 1.372(7) . ? C30 F3 1.329(5) . ? C30 C31 1.372(7) . ? C31 F4 1.336(6) . ? C31 C32 1.372(7) . ? C32 F5 1.345(5) . ? C33 C38 1.365(7) . ? C33 C34 1.391(7) . ? C33 N2 1.418(6) . ? C34 F6 1.332(6) . ? C34 C35 1.367(7) . ? C35 F10 1.351(6) . ? C35 C36 1.365(8) . ? C36 F9 1.333(6) . ? C36 C37 1.371(8) . ? C37 F8 1.329(6) . ? C37 C38 1.375(7) . ? C38 F7 1.347(6) . ? 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 C1 C2 124.7(4) . . ? C6 C1 C10 123.1(4) . . ? C2 C1 C10 112.2(4) . . ? C3 C2 C1 117.8(4) . . ? C3 C2 C12 137.3(4) . . ? C1 C2 C12 104.9(4) . . ? C2 C3 C4 117.5(4) . . ? C2 C3 C23 128.7(5) . . ? C4 C3 C23 113.9(4) . . ? C5 C4 C3 123.8(5) . . ? C4 C5 C6 119.7(4) . . ? C1 C6 C7 117.6(5) . . ? C1 C6 C5 116.6(5) . . ? C7 C6 C5 125.8(5) . . ? C8 C7 C6 119.1(4) . . ? C7 C8 C9 125.0(5) . . ? C10 C9 C8 117.1(4) . . ? C10 C9 C24 127.1(4) . . ? C8 C9 C24 115.8(4) . . ? C9 C10 C1 118.0(4) . . ? C9 C10 C11 137.6(4) . . ? C1 C10 C11 104.4(4) . . ? C12 C11 C10 109.7(4) . . ? C12 C11 C16 115.0(4) . . ? C10 C11 C16 135.3(4) . . ? C11 C12 C2 108.8(4) . . ? C11 C12 C13 115.8(4) . . ? C2 C12 C13 135.4(4) . . ? C12 C13 C26 121.1(4) . . ? C12 C13 C14 107.8(4) . . ? C26 C13 C14 108.4(4) . . ? C12 C13 C18 105.4(4) . . ? C26 C13 C18 108.4(4) . . ? C14 C13 C18 104.5(3) . . ? C21 C14 C15 105.9(4) . . ? C21 C14 C13 113.6(4) . . ? C15 C14 C13 110.0(3) . . ? C22 C15 C14 105.2(4) . . ? C22 C15 C16 111.6(4) . . ? C14 C15 C16 112.9(4) . . ? C11 C16 C25 121.6(4) . . ? C11 C16 C15 105.7(3) . . ? C25 C16 C15 107.5(4) . . ? C11 C16 C17 107.3(4) . . ? C25 C16 C17 108.9(4) . . ? C15 C16 C17 104.6(3) . . ? C20 C17 C18 105.1(4) . . ? C20 C17 C16 110.9(4) . . ? C18 C17 C16 110.8(4) . . ? C19 C18 C17 105.8(4) . . ? C19 C18 C13 111.4(4) . . ? C17 C18 C13 111.7(4) . . ? O1 C19 N1 122.7(5) . . ? O1 C19 C18 129.8(5) . . ? N1 C19 C18 107.5(4) . . ? O2 C20 N1 124.0(4) . . ? O2 C20 C17 128.7(5) . . ? N1 C20 C17 107.3(4) . . ? O3 C21 N2 123.7(4) . . ? O3 C21 C14 129.1(5) . . ? N2 C21 C14 107.2(4) . . ? O4 C22 N2 122.4(4) . . ? O4 C22 C15 130.3(4) . . ? N2 C22 C15 107.3(4) . . ? C28 C27 C32 117.8(4) . . ? C28 C27 N1 121.6(4) . . ? C32 C27 N1 120.4(4) . . ? F1 C28 C29 119.4(4) . . ? F1 C28 C27 119.4(4) . . ? C29 C28 C27 121.2(5) . . ? F2 C29 C30 120.0(5) . . ? F2 C29 C28 120.4(5) . . ? C30 C29 C28 119.6(4) . . ? F3 C30 C29 119.7(4) . . ? F3 C30 C31 119.9(4) . . ? C29 C30 C31 120.2(4) . . ? F4 C31 C30 120.7(4) . . ? F4 C31 C32 119.7(4) . . ? C30 C31 C32 119.5(5) . . ? F5 C32 C31 118.9(4) . . ? F5 C32 C27 119.6(4) . . ? C31 C32 C27 121.5(4) . . ? C38 C33 C34 118.5(4) . . ? C38 C33 N2 120.4(4) . . ? C34 C33 N2 120.9(4) . . ? F6 C34 C35 120.5(4) . . ? F6 C34 C33 119.3(4) . . ? C35 C34 C33 120.1(5) . . ? F10 C35 C36 119.4(5) . . ? F10 C35 C34 120.2(5) . . ? C36 C35 C34 120.5(5) . . ? F9 C36 C35 120.3(5) . . ? F9 C36 C37 119.7(5) . . ? C35 C36 C37 120.0(5) . . ? F8 C37 C36 120.3(5) . . ? F8 C37 C38 120.2(5) . . ? C36 C37 C38 119.4(5) . . ? F7 C38 C33 120.0(4) . . ? F7 C38 C37 118.6(5) . . ? C33 C38 C37 121.3(5) . . ? C20 N1 C19 114.0(4) . . ? C20 N1 C27 125.6(4) . . ? C19 N1 C27 120.3(4) . . ? C21 N2 C22 113.7(4) . . ? C21 N2 C33 125.5(4) . . ? C22 N2 C33 120.8(4) . . ? _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 26.48 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 1.084 _refine_diff_density_min -0.239 _refine_diff_density_rms 0.060 # Attachment '3a.CIF' data_prospec _database_code_depnum_ccdc_archive 'CCDC 876635' #TrackingRef '3a.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C28 H8 F5 N O2' _chemical_formula_weight 485.35 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0727 0.0534 '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 16.4353(5) _cell_length_b 7.3459(2) _cell_length_c 16.4520(4) _cell_angle_alpha 90.00 _cell_angle_beta 108.036(2) _cell_angle_gamma 90.00 _cell_volume 1888.68(9) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 3883 _cell_measurement_theta_min 4.6 _cell_measurement_theta_max 65.0 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.13 _exptl_crystal_size_mid 0.02 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.707 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 976 _exptl_absorpt_coefficient_mu 1.227 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8528 _exptl_absorpt_correction_T_max 0.9903 _exptl_absorpt_process_details 'SADABS (Bruker-AXS)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'micro source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker X8 Prospector' _diffrn_measurement_method 'phi scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 17814 _diffrn_reflns_av_R_equivalents 0.0530 _diffrn_reflns_av_sigmaI/netI 0.0375 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 3.32 _diffrn_reflns_theta_max 66.41 _reflns_number_total 3211 _reflns_number_gt 2563 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (BRUKER-AXS)' _computing_cell_refinement 'SAINT (BRUKER-AXS)' _computing_data_reduction 'SAINT (BRUKER-AXS)' _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^)+(0.0483P)^2^+0.7501P] 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 3211 _refine_ls_number_parameters 325 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0535 _refine_ls_R_factor_gt 0.0373 _refine_ls_wR_factor_ref 0.0961 _refine_ls_wR_factor_gt 0.0883 _refine_ls_goodness_of_fit_ref 1.019 _refine_ls_restrained_S_all 1.019 _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 0.88078(8) 0.02168(18) -0.32220(7) 0.0348(3) Uani 1 1 d . . . F2 F 0.89400(8) -0.26371(16) -0.21303(8) 0.0354(3) Uani 1 1 d . . . F3 F 0.86307(9) -0.21409(17) -0.06344(8) 0.0357(3) Uani 1 1 d . . . F4 F 0.80083(8) 0.40353(17) -0.13148(8) 0.0368(3) Uani 1 1 d . . . F5 F 0.83279(8) 0.35337(18) -0.28202(8) 0.0368(3) Uani 1 1 d . . . O1 O 0.94519(10) 0.1337(2) 0.07914(9) 0.0317(4) Uani 1 1 d . . . O2 O 0.66107(9) 0.1348(2) -0.07727(9) 0.0314(4) Uani 1 1 d . . . N1 N 0.80878(11) 0.1215(2) -0.01782(10) 0.0268(4) Uani 1 1 d . . . C1 C 0.86485(13) 0.0454(3) -0.24768(12) 0.0275(5) Uani 1 1 d . . . C2 C 0.84016(14) 0.2140(3) -0.22740(13) 0.0283(5) Uani 1 1 d . . . C3 C 0.82356(13) 0.2378(3) -0.15110(13) 0.0277(5) Uani 1 1 d . . . C4 C 0.83030(13) 0.0946(3) -0.09410(13) 0.0265(5) Uani 1 1 d . . . C5 C 0.86911(14) 0.1465(3) 0.06369(13) 0.0247(4) Uani 1 1 d . . . C6 C 0.81824(13) 0.1922(3) 0.12147(13) 0.0228(4) Uani 1 1 d . . . C7 C 0.84883(13) 0.2255(3) 0.21235(12) 0.0230(4) Uani 1 1 d . . . C8 C 0.78338(13) 0.2805(3) 0.24299(13) 0.0229(4) Uani 1 1 d . . . C9 C 0.79032(13) 0.2700(3) 0.33092(13) 0.0236(4) Uani 1 1 d . . . C10 C 0.70660(13) 0.2554(3) 0.33727(13) 0.0240(4) Uani 1 1 d . . . C11 C 0.68909(14) 0.1746(3) 0.40547(13) 0.0258(5) Uani 1 1 d . . . C12 C 0.76457(14) 0.1335(3) 0.47660(13) 0.0276(5) Uani 1 1 d . . . H1 H 0.7577 0.0954 0.5293 0.033 Uiso 1 1 calc R . . C13 C 0.87253(13) -0.0989(3) -0.19226(13) 0.0271(5) Uani 1 1 d . . . C14 C 0.85591(14) -0.0727(3) -0.11602(13) 0.0269(5) Uani 1 1 d . . . C15 C 0.73178(13) 0.1894(3) 0.07422(13) 0.0233(4) Uani 1 1 d . . . C16 C 0.66386(13) 0.2158(3) 0.11151(12) 0.0233(4) Uani 1 1 d . . . C17 C 0.69540(13) 0.2740(3) 0.19512(13) 0.0231(4) Uani 1 1 d . . . C18 C 0.64792(13) 0.2576(3) 0.25361(12) 0.0233(4) Uani 1 1 d . . . C19 C 0.84618(14) 0.1480(3) 0.47030(13) 0.0273(5) Uani 1 1 d . . . H6 H 0.8936 0.1199 0.5188 0.033 Uiso 1 1 calc R . . C20 C 0.86183(14) 0.2045(3) 0.39206(13) 0.0253(5) Uani 1 1 d . . . C21 C 0.93447(14) 0.1732(3) 0.36232(13) 0.0260(4) Uani 1 1 d . . . H5 H 0.9882 0.1453 0.4028 0.031 Uiso 1 1 calc R . . C22 C 0.92821(14) 0.1827(3) 0.27683(13) 0.0258(5) Uani 1 1 d . . . H4 H 0.9777 0.1603 0.2601 0.031 Uiso 1 1 calc R . . C23 C 0.60163(14) 0.1143(3) 0.38718(13) 0.0281(5) Uani 1 1 d . . . H10 H 0.5826 0.0732 0.4330 0.034 Uiso 1 1 calc R . . C24 C 0.54472(14) 0.1144(3) 0.30549(13) 0.0274(5) Uani 1 1 d . . . H9 H 0.4881 0.0715 0.2968 0.033 Uiso 1 1 calc R . . C25 C 0.56851(13) 0.1779(3) 0.23250(13) 0.0261(5) Uani 1 1 d . . . C26 C 0.52995(14) 0.1418(3) 0.14218(13) 0.0268(4) Uani 1 1 d . . . H8 H 0.4719 0.1037 0.1219 0.032 Uiso 1 1 calc R . . C27 C 0.57539(13) 0.1613(3) 0.08454(13) 0.0260(5) Uani 1 1 d . . . H7 H 0.5475 0.1380 0.0257 0.031 Uiso 1 1 calc R . . C28 C 0.72421(13) 0.1456(3) -0.01592(13) 0.0257(5) 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 0.0363(7) 0.0485(8) 0.0229(6) 0.0007(5) 0.0137(5) 0.0031(6) F2 0.0445(8) 0.0288(7) 0.0382(7) -0.0063(5) 0.0207(6) -0.0006(5) F3 0.0507(8) 0.0281(7) 0.0348(7) 0.0072(5) 0.0231(6) 0.0015(5) F4 0.0476(8) 0.0296(7) 0.0362(7) 0.0025(5) 0.0175(6) 0.0090(6) F5 0.0408(8) 0.0398(8) 0.0316(7) 0.0146(6) 0.0140(6) 0.0067(6) O1 0.0297(10) 0.0397(9) 0.0273(8) -0.0013(6) 0.0110(6) 0.0012(7) O2 0.0313(9) 0.0376(9) 0.0244(8) 0.0002(6) 0.0073(7) -0.0003(7) N1 0.0282(10) 0.0323(10) 0.0205(9) -0.0002(7) 0.0086(7) 0.0004(7) C1 0.0259(12) 0.0402(13) 0.0182(10) -0.0017(9) 0.0096(8) -0.0013(9) C2 0.0281(12) 0.0322(12) 0.0244(11) 0.0069(9) 0.0079(8) 0.0014(9) C3 0.0270(12) 0.0262(12) 0.0292(11) -0.0011(9) 0.0080(9) 0.0016(8) C4 0.0267(11) 0.0317(12) 0.0212(10) -0.0022(8) 0.0077(8) -0.0005(8) C5 0.0283(13) 0.0220(11) 0.0238(10) 0.0012(8) 0.0083(8) 0.0003(8) C6 0.0304(12) 0.0148(10) 0.0245(10) 0.0012(8) 0.0104(8) -0.0005(8) C7 0.0301(11) 0.0146(10) 0.0248(11) 0.0004(8) 0.0092(8) -0.0034(8) C8 0.0306(12) 0.0148(10) 0.0243(10) 0.0001(8) 0.0099(8) -0.0018(8) C9 0.0341(12) 0.0143(10) 0.0242(10) -0.0047(8) 0.0116(9) -0.0029(8) C10 0.0327(12) 0.0153(10) 0.0257(10) -0.0033(8) 0.0115(8) 0.0014(8) C11 0.0371(13) 0.0186(11) 0.0254(11) -0.0054(8) 0.0150(9) 0.0007(8) C12 0.0412(13) 0.0215(11) 0.0222(10) -0.0023(8) 0.0129(9) -0.0004(9) C13 0.0271(12) 0.0273(12) 0.0277(11) -0.0041(9) 0.0094(9) -0.0002(8) C14 0.0293(12) 0.0271(11) 0.0249(11) 0.0039(9) 0.0092(8) -0.0018(8) C15 0.0312(12) 0.0161(10) 0.0238(10) 0.0023(8) 0.0100(8) 0.0012(8) C16 0.0312(12) 0.0159(10) 0.0238(10) 0.0049(8) 0.0098(8) 0.0039(8) C17 0.0315(12) 0.0145(10) 0.0248(10) 0.0031(8) 0.0106(8) 0.0030(8) C18 0.0307(12) 0.0162(10) 0.0248(11) 0.0011(8) 0.0114(8) 0.0037(8) C19 0.0368(13) 0.0214(11) 0.0221(10) -0.0042(8) 0.0070(9) -0.0009(9) C20 0.0338(12) 0.0185(10) 0.0235(10) -0.0061(8) 0.0087(9) -0.0043(8) C21 0.0289(12) 0.0225(11) 0.0243(10) -0.0033(8) 0.0050(8) -0.0024(8) C22 0.0289(12) 0.0231(11) 0.0272(11) -0.0026(8) 0.0114(8) -0.0035(8) C23 0.0376(13) 0.0221(11) 0.0301(11) -0.0023(8) 0.0183(9) 0.0019(9) C24 0.0303(12) 0.0223(11) 0.0333(12) -0.0017(9) 0.0154(9) 0.0028(8) C25 0.0295(12) 0.0199(11) 0.0308(11) 0.0010(8) 0.0122(9) 0.0056(8) C26 0.0267(11) 0.0221(11) 0.0310(11) 0.0012(9) 0.0081(8) 0.0029(8) C27 0.0311(12) 0.0217(11) 0.0246(10) 0.0023(8) 0.0079(8) 0.0043(8) C28 0.0302(12) 0.0221(11) 0.0253(11) 0.0028(8) 0.0094(9) 0.0003(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag F1 C1 1.342(2) . ? F2 C13 1.335(2) . ? F3 C14 1.333(2) . ? F4 C3 1.342(2) . ? F5 C2 1.343(2) . ? O1 C5 1.200(3) . ? O2 C28 1.205(2) . ? N1 C28 1.411(3) . ? N1 C5 1.411(3) . ? N1 C4 1.419(3) . ? C1 C2 1.376(3) . ? C1 C13 1.378(3) . ? C2 C3 1.376(3) . ? C3 C4 1.391(3) . ? C4 C14 1.383(3) . ? C5 C6 1.486(3) . ? C6 C15 1.393(3) . ? C6 C7 1.443(3) . ? C7 C8 1.382(3) . ? C7 C22 1.439(3) . ? C8 C17 1.417(3) . ? C8 C9 1.418(3) . ? C9 C20 1.375(3) . ? C9 C10 1.416(3) . ? C10 C11 1.376(3) . ? C10 C18 1.415(3) . ? C11 C23 1.444(3) . ? C11 C12 1.449(3) . ? C12 C19 1.381(3) . ? C12 H1 0.9500 . ? C13 C14 1.377(3) . ? C15 C16 1.444(3) . ? C15 C28 1.485(3) . ? C16 C17 1.379(3) . ? C16 C27 1.440(3) . ? C17 C18 1.419(3) . ? C18 C25 1.373(3) . ? C19 C20 1.449(3) . ? C19 H6 0.9500 . ? C20 C21 1.442(3) . ? C21 C22 1.380(3) . ? C21 H5 0.9500 . ? C22 H4 0.9500 . ? C23 C24 1.379(3) . ? C23 H10 0.9500 . ? C24 C25 1.450(3) . ? C24 H9 0.9500 . ? C25 C26 1.448(3) . ? C26 C27 1.384(3) . ? C26 H8 0.9500 . ? C27 H7 0.9500 . ? 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 C28 N1 C5 111.70(16) . . ? C28 N1 C4 123.64(17) . . ? C5 N1 C4 124.34(17) . . ? F1 C1 C2 119.61(18) . . ? F1 C1 C13 120.06(19) . . ? C2 C1 C13 120.33(18) . . ? F5 C2 C3 120.74(19) . . ? F5 C2 C1 119.75(18) . . ? C3 C2 C1 119.51(19) . . ? F4 C3 C2 118.92(18) . . ? F4 C3 C4 119.60(18) . . ? C2 C3 C4 121.48(19) . . ? C14 C4 C3 117.61(18) . . ? C14 C4 N1 122.26(18) . . ? C3 C4 N1 120.10(18) . . ? O1 C5 N1 124.79(18) . . ? O1 C5 C6 129.64(19) . . ? N1 C5 C6 105.56(17) . . ? C15 C6 C7 123.28(18) . . ? C15 C6 C5 108.57(17) . . ? C7 C6 C5 128.07(19) . . ? C8 C7 C22 115.19(18) . . ? C8 C7 C6 111.50(18) . . ? C22 C7 C6 132.25(18) . . ? C7 C8 C17 124.26(18) . . ? C7 C8 C9 122.03(19) . . ? C17 C8 C9 108.13(18) . . ? C20 C9 C10 123.33(19) . . ? C20 C9 C8 123.09(19) . . ? C10 C9 C8 107.85(18) . . ? C11 C10 C18 123.1(2) . . ? C11 C10 C9 123.1(2) . . ? C18 C10 C9 108.21(17) . . ? C10 C11 C23 114.11(19) . . ? C10 C11 C12 113.90(19) . . ? C23 C11 C12 130.72(19) . . ? C19 C12 C11 122.13(19) . . ? C19 C12 H1 118.9 . . ? C11 C12 H1 118.9 . . ? F2 C13 C14 120.16(18) . . ? F2 C13 C1 120.37(18) . . ? C14 C13 C1 119.45(19) . . ? F3 C14 C13 118.64(18) . . ? F3 C14 C4 119.74(18) . . ? C13 C14 C4 121.60(19) . . ? C6 C15 C16 123.39(18) . . ? C6 C15 C28 108.44(17) . . ? C16 C15 C28 128.09(18) . . ? C17 C16 C27 115.19(18) . . ? C17 C16 C15 111.36(18) . . ? C27 C16 C15 132.20(18) . . ? C16 C17 C8 124.65(19) . . ? C16 C17 C18 122.29(19) . . ? C8 C17 C18 107.87(18) . . ? C25 C18 C10 123.31(18) . . ? C25 C18 C17 122.93(19) . . ? C10 C18 C17 107.94(18) . . ? C12 C19 C20 122.15(19) . . ? C12 C19 H6 118.9 . . ? C20 C19 H6 118.9 . . ? C9 C20 C21 114.67(18) . . ? C9 C20 C19 113.79(19) . . ? C21 C20 C19 130.45(19) . . ? C22 C21 C20 122.0(2) . . ? C22 C21 H5 119.0 . . ? C20 C21 H5 119.0 . . ? C21 C22 C7 121.80(19) . . ? C21 C22 H4 119.1 . . ? C7 C22 H4 119.1 . . ? C24 C23 C11 122.26(19) . . ? C24 C23 H10 118.9 . . ? C11 C23 H10 118.9 . . ? C23 C24 C25 122.1(2) . . ? C23 C24 H9 118.9 . . ? C25 C24 H9 118.9 . . ? C18 C25 C26 114.67(18) . . ? C18 C25 C24 113.99(19) . . ? C26 C25 C24 130.3(2) . . ? C27 C26 C25 121.8(2) . . ? C27 C26 H8 119.1 . . ? C25 C26 H8 119.1 . . ? C26 C27 C16 121.69(19) . . ? C26 C27 H7 119.2 . . ? C16 C27 H7 119.2 . . ? O2 C28 N1 124.87(19) . . ? O2 C28 C15 129.41(19) . . ? N1 C28 C15 105.71(17) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag F1 C1 C2 F5 -0.5(3) . . . . ? C13 C1 C2 F5 -179.90(18) . . . . ? F1 C1 C2 C3 179.77(19) . . . . ? C13 C1 C2 C3 0.3(3) . . . . ? F5 C2 C3 F4 -0.8(3) . . . . ? C1 C2 C3 F4 178.97(19) . . . . ? F5 C2 C3 C4 179.54(18) . . . . ? C1 C2 C3 C4 -0.7(3) . . . . ? F4 C3 C4 C14 -178.47(19) . . . . ? C2 C3 C4 C14 1.2(3) . . . . ? F4 C3 C4 N1 3.4(3) . . . . ? C2 C3 C4 N1 -177.0(2) . . . . ? C28 N1 C4 C14 -106.8(2) . . . . ? C5 N1 C4 C14 80.2(3) . . . . ? C28 N1 C4 C3 71.3(3) . . . . ? C5 N1 C4 C3 -101.7(2) . . . . ? C28 N1 C5 O1 -179.90(19) . . . . ? C4 N1 C5 O1 -6.1(3) . . . . ? C28 N1 C5 C6 -0.7(2) . . . . ? C4 N1 C5 C6 173.06(18) . . . . ? O1 C5 C6 C15 -179.7(2) . . . . ? N1 C5 C6 C15 1.2(2) . . . . ? O1 C5 C6 C7 -2.8(4) . . . . ? N1 C5 C6 C7 178.02(18) . . . . ? C15 C6 C7 C8 -9.1(3) . . . . ? C5 C6 C7 C8 174.49(19) . . . . ? C15 C6 C7 C22 158.3(2) . . . . ? C5 C6 C7 C22 -18.1(3) . . . . ? C22 C7 C8 C17 -159.20(18) . . . . ? C6 C7 C8 C17 10.5(3) . . . . ? C22 C7 C8 C9 -8.7(3) . . . . ? C6 C7 C8 C9 161.00(18) . . . . ? C7 C8 C9 C20 -0.2(3) . . . . ? C17 C8 C9 C20 154.47(19) . . . . ? C7 C8 C9 C10 -154.17(18) . . . . ? C17 C8 C9 C10 0.5(2) . . . . ? C20 C9 C10 C11 0.1(3) . . . . ? C8 C9 C10 C11 154.06(19) . . . . ? C20 C9 C10 C18 -154.14(19) . . . . ? C8 C9 C10 C18 -0.2(2) . . . . ? C18 C10 C11 C23 -8.1(3) . . . . ? C9 C10 C11 C23 -158.65(18) . . . . ? C18 C10 C11 C12 160.42(18) . . . . ? C9 C10 C11 C12 9.9(3) . . . . ? C10 C11 C12 C19 -9.7(3) . . . . ? C23 C11 C12 C19 156.4(2) . . . . ? F1 C1 C13 F2 -1.4(3) . . . . ? C2 C1 C13 F2 177.99(19) . . . . ? F1 C1 C13 C14 -179.94(19) . . . . ? C2 C1 C13 C14 -0.5(3) . . . . ? F2 C13 C14 F3 1.0(3) . . . . ? C1 C13 C14 F3 179.53(18) . . . . ? F2 C13 C14 C4 -177.45(19) . . . . ? C1 C13 C14 C4 1.0(3) . . . . ? C3 C4 C14 F3 -179.83(18) . . . . ? N1 C4 C14 F3 -1.7(3) . . . . ? C3 C4 C14 C13 -1.4(3) . . . . ? N1 C4 C14 C13 176.74(19) . . . . ? C7 C6 C15 C16 -1.3(3) . . . . ? C5 C6 C15 C16 175.74(18) . . . . ? C7 C6 C15 C28 -178.22(17) . . . . ? C5 C6 C15 C28 -1.2(2) . . . . ? C6 C15 C16 C17 10.2(3) . . . . ? C28 C15 C16 C17 -173.46(19) . . . . ? C6 C15 C16 C27 -156.0(2) . . . . ? C28 C15 C16 C27 20.3(3) . . . . ? C27 C16 C17 C8 159.71(18) . . . . ? C15 C16 C17 C8 -9.1(3) . . . . ? C27 C16 C17 C18 8.3(3) . . . . ? C15 C16 C17 C18 -160.47(18) . . . . ? C7 C8 C17 C16 -1.5(3) . . . . ? C9 C8 C17 C16 -155.39(19) . . . . ? C7 C8 C17 C18 153.40(19) . . . . ? C9 C8 C17 C18 -0.5(2) . . . . ? C11 C10 C18 C25 -0.7(3) . . . . ? C9 C10 C18 C25 153.60(19) . . . . ? C11 C10 C18 C17 -154.39(19) . . . . ? C9 C10 C18 C17 -0.1(2) . . . . ? C16 C17 C18 C25 2.1(3) . . . . ? C8 C17 C18 C25 -153.43(19) . . . . ? C16 C17 C18 C10 155.97(19) . . . . ? C8 C17 C18 C10 0.4(2) . . . . ? C11 C12 C19 C20 -0.2(3) . . . . ? C10 C9 C20 C21 159.11(18) . . . . ? C8 C9 C20 C21 9.1(3) . . . . ? C10 C9 C20 C19 -10.2(3) . . . . ? C8 C9 C20 C19 -160.22(18) . . . . ? C12 C19 C20 C9 10.1(3) . . . . ? C12 C19 C20 C21 -157.1(2) . . . . ? C9 C20 C21 C22 -9.1(3) . . . . ? C19 C20 C21 C22 158.0(2) . . . . ? C20 C21 C22 C7 0.4(3) . . . . ? C8 C7 C22 C21 8.5(3) . . . . ? C6 C7 C22 C21 -158.5(2) . . . . ? C10 C11 C23 C24 8.9(3) . . . . ? C12 C11 C23 C24 -157.3(2) . . . . ? C11 C23 C24 C25 -1.0(3) . . . . ? C10 C18 C25 C26 -160.67(18) . . . . ? C17 C18 C25 C26 -10.8(3) . . . . ? C10 C18 C25 C24 8.6(3) . . . . ? C17 C18 C25 C24 158.47(18) . . . . ? C23 C24 C25 C18 -7.7(3) . . . . ? C23 C24 C25 C26 159.5(2) . . . . ? C18 C25 C26 C27 9.2(3) . . . . ? C24 C25 C26 C27 -157.9(2) . . . . ? C25 C26 C27 C16 1.0(3) . . . . ? C17 C16 C27 C26 -9.7(3) . . . . ? C15 C16 C27 C26 156.1(2) . . . . ? C5 N1 C28 O2 178.70(19) . . . . ? C4 N1 C28 O2 4.9(3) . . . . ? C5 N1 C28 C15 0.0(2) . . . . ? C4 N1 C28 C15 -173.81(18) . . . . ? C6 C15 C28 O2 -177.9(2) . . . . ? C16 C15 C28 O2 5.4(4) . . . . ? C6 C15 C28 N1 0.8(2) . . . . ? C16 C15 C28 N1 -175.99(19) . . . . ? _diffrn_measured_fraction_theta_max 0.967 _diffrn_reflns_theta_full 66.41 _diffrn_measured_fraction_theta_full 0.967 _refine_diff_density_max 0.438 _refine_diff_density_min -0.185 _refine_diff_density_rms 0.046