# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Prof. Yulia Budnikova' _publ_contact_author_email yulia@iopc.ru _publ_section_title ; Electrochemical nickel-induced fluoroalkylation: synthetic, structural and mechanistical study ; loop_ _publ_author_name D.Mikhaylov T.Gryaznova Yu.Dudkina M.S.Khrizanphorov O.Kataeva # Attachment '- cif_5.txt' data_bud3 _database_code_depnum_ccdc_archive 'CCDC 832892' #TrackingRef '- cif_5.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C26 H14 F26 N2' _chemical_formula_sum 'C26 H14 F26 N2' _chemical_formula_weight 848.39 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 triclinic _symmetry_space_group_name_H-M P-1 _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 5.4351(3) _cell_length_b 9.9164(4) _cell_length_c 14.5715(6) _cell_angle_alpha 83.270(4) _cell_angle_beta 80.137(4) _cell_angle_gamma 86.720(4) _cell_volume 767.86(6) _cell_formula_units_Z 1 _cell_measurement_temperature 198(2) _cell_measurement_reflns_used 4268 _cell_measurement_theta_min 3.72 _cell_measurement_theta_max 25.40 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.39 _exptl_crystal_size_mid 0.39 _exptl_crystal_size_min 0.22 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.835 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 418 _exptl_absorpt_coefficient_mu 0.220 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9193 _exptl_absorpt_correction_T_max 0.9533 _exptl_absorpt_process_details 'SADABS version 2.10 (Sheldrick,Bruker AXS Inc.,2002)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 198(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 KappaCCD _diffrn_measurement_method \f _diffrn_detector_area_resol_mean 9 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15277 _diffrn_reflns_av_R_equivalents 0.0179 _diffrn_reflns_av_sigmaI/netI 0.0130 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 3.34 _diffrn_reflns_theta_max 25.40 _reflns_number_total 2814 _reflns_number_gt 2358 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius BV, 1999)' _computing_cell_refinement 'Dirax/lsq (Duisenberg, 1992)' _computing_data_reduction 'EvalCCD (Duisenberg et al., 2003)' _computing_structure_solution 'SIR2004 (Burla et al., 2005)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997), WinGX (Farrugia 1999), PLATON (Spek 2005)' _computing_molecular_graphics 'ORTEP-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX (Farrugia 1999), enCIFer (Allen et al. 2004)' _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^)+(0.0582P)^2^+0.3148P] 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 2814 _refine_ls_number_parameters 244 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0446 _refine_ls_R_factor_gt 0.0364 _refine_ls_wR_factor_ref 0.1089 _refine_ls_wR_factor_gt 0.1032 _refine_ls_goodness_of_fit_ref 1.068 _refine_ls_restrained_S_all 1.068 _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 0.4898(3) 0.06408(16) 0.02634(12) 0.0312(4) Uani 1 1 d . . . H1A H 0.3098 0.0820 0.0521 0.037 Uiso 1 1 calc R . . C2 C 0.6352(3) 0.03709(17) 0.10911(12) 0.0332(4) Uani 1 1 d . . . H2A H 0.5653 -0.0424 0.1510 0.040 Uiso 1 1 calc R . . H2B H 0.8118 0.0136 0.0846 0.040 Uiso 1 1 calc R . . C3 C 0.6266(3) 0.15592(17) 0.16555(12) 0.0329(4) Uani 1 1 d . . . C4 C 0.6985(3) 0.11705(16) 0.26344(12) 0.0339(4) Uani 1 1 d . . . C5 C 0.7201(3) 0.23686(17) 0.32126(12) 0.0330(4) Uani 1 1 d . . . C6 C 0.7326(3) 0.19494(17) 0.42620(13) 0.0374(4) Uani 1 1 d . . . C7 C 0.8125(4) 0.30827(19) 0.47798(14) 0.0417(4) Uani 1 1 d . . . C8 C 0.7633(5) 0.2845(2) 0.58513(15) 0.0552(6) Uani 1 1 d . . . C9 C 0.5830(3) 0.18736(17) -0.03951(12) 0.0332(4) Uani 1 1 d . . . N10 N 0.8134(3) 0.17449(16) -0.08895(11) 0.0409(4) Uani 1 1 d . . . C11 C 0.8984(4) 0.2819(2) -0.14746(15) 0.0532(5) Uani 1 1 d . . . H11A H 1.0605 0.2743 -0.1837 0.064 Uiso 1 1 calc R . . C12 C 0.7645(5) 0.4029(2) -0.15823(16) 0.0616(7) Uani 1 1 d . . . H12A H 0.8338 0.4770 -0.2002 0.074 Uiso 1 1 calc R . . C13 C 0.5295(5) 0.4149(2) -0.10733(16) 0.0589(6) Uani 1 1 d . . . H13A H 0.4330 0.4975 -0.1134 0.071 Uiso 1 1 calc R . . C14 C 0.4347(4) 0.30492(18) -0.04690(14) 0.0445(5) Uani 1 1 d . . . H14A H 0.2715 0.3100 -0.0113 0.053 Uiso 1 1 calc R . . F15 F 0.3951(2) 0.21721(12) 0.17753(8) 0.0473(3) Uani 1 1 d . . . F16 F 0.7854(2) 0.25374(10) 0.12132(7) 0.0441(3) Uani 1 1 d . . . F17 F 0.9197(2) 0.04800(11) 0.25222(8) 0.0506(3) Uani 1 1 d . . . F18 F 0.5253(3) 0.03416(12) 0.31330(8) 0.0556(3) Uani 1 1 d . . . F19 F 0.9290(2) 0.30271(12) 0.28351(8) 0.0500(3) Uani 1 1 d . . . F20 F 0.5250(2) 0.32394(11) 0.31572(8) 0.0489(3) Uani 1 1 d . . . F21 F 0.5030(2) 0.15750(14) 0.46966(8) 0.0589(4) Uani 1 1 d . . . F22 F 0.8889(3) 0.08829(12) 0.43451(9) 0.0622(4) Uani 1 1 d . . . F23 F 0.6972(3) 0.42552(11) 0.45203(8) 0.0545(3) Uani 1 1 d . . . F24 F 1.0587(2) 0.32308(15) 0.45248(9) 0.0614(4) Uani 1 1 d . . . F25 F 0.5192(3) 0.28997(18) 0.61804(10) 0.0833(5) Uani 1 1 d . . . F26 F 0.8636(4) 0.38106(15) 0.61952(10) 0.0848(5) Uani 1 1 d . . . F27 F 0.8546(3) 0.16614(14) 0.61547(10) 0.0746(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 C1 0.0304(8) 0.0227(8) 0.0390(9) 0.0004(7) -0.0052(7) 0.0011(6) C2 0.0366(9) 0.0239(8) 0.0382(9) 0.0006(7) -0.0069(7) 0.0005(7) C3 0.0306(9) 0.0247(8) 0.0411(10) 0.0014(7) -0.0038(7) 0.0012(7) C4 0.0372(9) 0.0233(8) 0.0392(10) 0.0004(7) -0.0040(7) -0.0002(7) C5 0.0338(9) 0.0240(8) 0.0379(9) 0.0013(7) -0.0001(7) 0.0001(7) C6 0.0444(10) 0.0251(9) 0.0406(10) 0.0022(7) -0.0059(8) -0.0002(7) C7 0.0503(11) 0.0307(9) 0.0424(11) -0.0028(8) -0.0042(8) 0.0010(8) C8 0.0811(17) 0.0402(11) 0.0440(12) -0.0044(9) -0.0088(11) -0.0048(11) C9 0.0416(10) 0.0237(8) 0.0362(9) -0.0007(7) -0.0132(7) -0.0019(7) N10 0.0414(9) 0.0378(8) 0.0416(9) 0.0049(7) -0.0059(7) -0.0082(7) C11 0.0618(13) 0.0537(13) 0.0431(11) 0.0074(9) -0.0076(10) -0.0236(11) C12 0.102(2) 0.0371(11) 0.0474(13) 0.0124(9) -0.0216(13) -0.0273(12) C13 0.100(2) 0.0254(10) 0.0539(13) 0.0039(9) -0.0277(13) 0.0016(10) C14 0.0596(12) 0.0275(9) 0.0483(11) -0.0030(8) -0.0172(9) 0.0047(8) F15 0.0398(6) 0.0494(7) 0.0556(7) -0.0176(5) -0.0138(5) 0.0159(5) F16 0.0582(7) 0.0314(5) 0.0417(6) 0.0051(4) -0.0079(5) -0.0140(5) F17 0.0591(7) 0.0421(6) 0.0552(7) -0.0157(5) -0.0236(6) 0.0235(5) F18 0.0792(9) 0.0413(6) 0.0451(7) 0.0065(5) -0.0054(6) -0.0297(6) F19 0.0567(7) 0.0465(7) 0.0440(6) -0.0064(5) 0.0070(5) -0.0226(6) F20 0.0589(7) 0.0398(6) 0.0483(7) -0.0083(5) -0.0151(5) 0.0207(5) F21 0.0648(8) 0.0647(8) 0.0434(7) 0.0041(6) 0.0027(6) -0.0265(7) F22 0.0998(10) 0.0355(6) 0.0567(7) -0.0093(5) -0.0352(7) 0.0278(6) F23 0.0828(9) 0.0284(6) 0.0502(7) -0.0039(5) -0.0093(6) 0.0097(6) F24 0.0488(7) 0.0750(9) 0.0622(8) -0.0170(7) -0.0044(6) -0.0136(6) F25 0.0919(12) 0.0980(12) 0.0505(8) -0.0124(8) 0.0177(8) -0.0022(9) F26 0.1508(16) 0.0607(9) 0.0478(8) -0.0121(6) -0.0165(9) -0.0334(10) F27 0.1208(13) 0.0499(8) 0.0556(8) 0.0057(6) -0.0322(8) 0.0057(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 C9 1.517(2) . ? C1 C2 1.542(2) . ? C1 C1 1.549(3) 2_655 ? C1 H1A 1.0000 . ? C2 C3 1.508(2) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 F15 1.359(2) . ? C3 F16 1.3639(19) . ? C3 C4 1.543(3) . ? C4 F18 1.343(2) . ? C4 F17 1.344(2) . ? C4 C5 1.556(2) . ? C5 F20 1.336(2) . ? C5 F19 1.343(2) . ? C5 C6 1.549(3) . ? C6 F22 1.326(2) . ? C6 F21 1.350(2) . ? C6 C7 1.545(3) . ? C7 F23 1.335(2) . ? C7 F24 1.338(2) . ? C7 C8 1.531(3) . ? C8 F27 1.306(3) . ? C8 F26 1.316(3) . ? C8 F25 1.331(3) . ? C9 N10 1.341(2) . ? C9 C14 1.383(3) . ? N10 C11 1.335(2) . ? C11 C12 1.375(4) . ? C11 H11A 0.9500 . ? C12 C13 1.369(4) . ? C12 H12A 0.9500 . ? C13 C14 1.384(3) . ? C13 H13A 0.9500 . ? C14 H14A 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 C9 C1 C2 111.56(14) . . ? C9 C1 C1 111.00(18) . 2_655 ? C2 C1 C1 109.42(16) . 2_655 ? C9 C1 H1A 108.3 . . ? C2 C1 H1A 108.3 . . ? C1 C1 H1A 108.3 2_655 . ? C3 C2 C1 113.74(14) . . ? C3 C2 H2A 108.8 . . ? C1 C2 H2A 108.8 . . ? C3 C2 H2B 108.8 . . ? C1 C2 H2B 108.8 . . ? H2A C2 H2B 107.7 . . ? F15 C3 F16 105.99(13) . . ? F15 C3 C2 111.05(14) . . ? F16 C3 C2 111.67(14) . . ? F15 C3 C4 107.71(14) . . ? F16 C3 C4 106.40(14) . . ? C2 C3 C4 113.60(14) . . ? F18 C4 F17 108.55(14) . . ? F18 C4 C3 107.88(14) . . ? F17 C4 C3 107.82(14) . . ? F18 C4 C5 108.00(14) . . ? F17 C4 C5 108.20(14) . . ? C3 C4 C5 116.19(14) . . ? F20 C5 F19 108.07(14) . . ? F20 C5 C6 108.19(14) . . ? F19 C5 C6 107.49(14) . . ? F20 C5 C4 109.29(14) . . ? F19 C5 C4 108.64(14) . . ? C6 C5 C4 114.96(14) . . ? F22 C6 F21 107.92(15) . . ? F22 C6 C7 108.75(15) . . ? F21 C6 C7 107.70(15) . . ? F22 C6 C5 109.54(15) . . ? F21 C6 C5 108.10(15) . . ? C7 C6 C5 114.63(14) . . ? F23 C7 F24 107.85(16) . . ? F23 C7 C8 108.06(16) . . ? F24 C7 C8 106.49(17) . . ? F23 C7 C6 109.29(16) . . ? F24 C7 C6 108.76(15) . . ? C8 C7 C6 116.09(16) . . ? F27 C8 F26 109.6(2) . . ? F27 C8 F25 108.2(2) . . ? F26 C8 F25 107.1(2) . . ? F27 C8 C7 111.45(18) . . ? F26 C8 C7 109.52(18) . . ? F25 C8 C7 110.93(19) . . ? N10 C9 C14 123.05(17) . . ? N10 C9 C1 116.14(15) . . ? C14 C9 C1 120.81(17) . . ? C11 N10 C9 117.00(18) . . ? N10 C11 C12 123.7(2) . . ? N10 C11 H11A 118.2 . . ? C12 C11 H11A 118.2 . . ? C13 C12 C11 118.81(19) . . ? C13 C12 H12A 120.6 . . ? C11 C12 H12A 120.6 . . ? C12 C13 C14 118.9(2) . . ? C12 C13 H13A 120.5 . . ? C14 C13 H13A 120.5 . . ? C9 C14 C13 118.5(2) . . ? C9 C14 H14A 120.7 . . ? C13 C14 H14A 120.7 . . ? 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 C9 C1 C2 C3 57.0(2) . . . . ? C1 C1 C2 C3 -179.80(16) 2_655 . . . ? C1 C2 C3 F15 40.6(2) . . . . ? C1 C2 C3 F16 -77.45(18) . . . . ? C1 C2 C3 C4 162.21(14) . . . . ? F15 C3 C4 F18 58.72(17) . . . . ? F16 C3 C4 F18 172.02(13) . . . . ? C2 C3 C4 F18 -64.71(19) . . . . ? F15 C3 C4 F17 175.77(13) . . . . ? F16 C3 C4 F17 -70.93(16) . . . . ? C2 C3 C4 F17 52.34(19) . . . . ? F15 C3 C4 C5 -62.65(19) . . . . ? F16 C3 C4 C5 50.65(19) . . . . ? C2 C3 C4 C5 173.92(14) . . . . ? F18 C4 C5 F20 -76.41(17) . . . . ? F17 C4 C5 F20 166.28(13) . . . . ? C3 C4 C5 F20 44.9(2) . . . . ? F18 C4 C5 F19 165.89(14) . . . . ? F17 C4 C5 F19 48.58(18) . . . . ? C3 C4 C5 F19 -72.81(19) . . . . ? F18 C4 C5 C6 45.4(2) . . . . ? F17 C4 C5 C6 -71.87(18) . . . . ? C3 C4 C5 C6 166.74(14) . . . . ? F20 C5 C6 F22 166.90(14) . . . . ? F19 C5 C6 F22 -76.62(18) . . . . ? C4 C5 C6 F22 44.5(2) . . . . ? F20 C5 C6 F21 49.55(18) . . . . ? F19 C5 C6 F21 166.03(13) . . . . ? C4 C5 C6 F21 -72.89(19) . . . . ? F20 C5 C6 C7 -70.56(19) . . . . ? F19 C5 C6 C7 45.9(2) . . . . ? C4 C5 C6 C7 167.00(15) . . . . ? F22 C6 C7 F23 165.32(15) . . . . ? F21 C6 C7 F23 -77.98(18) . . . . ? C5 C6 C7 F23 42.4(2) . . . . ? F22 C6 C7 F24 47.8(2) . . . . ? F21 C6 C7 F24 164.52(14) . . . . ? C5 C6 C7 F24 -75.2(2) . . . . ? F22 C6 C7 C8 -72.2(2) . . . . ? F21 C6 C7 C8 44.5(2) . . . . ? C5 C6 C7 C8 164.84(17) . . . . ? F23 C7 C8 F27 175.09(18) . . . . ? F24 C7 C8 F27 -69.3(2) . . . . ? C6 C7 C8 F27 52.0(3) . . . . ? F23 C7 C8 F26 -63.5(2) . . . . ? F24 C7 C8 F26 52.2(2) . . . . ? C6 C7 C8 F26 173.39(18) . . . . ? F23 C7 C8 F25 54.5(2) . . . . ? F24 C7 C8 F25 170.11(17) . . . . ? C6 C7 C8 F25 -68.7(2) . . . . ? C2 C1 C9 N10 68.6(2) . . . . ? C1 C1 C9 N10 -53.7(2) 2_655 . . . ? C2 C1 C9 C14 -111.53(18) . . . . ? C1 C1 C9 C14 126.2(2) 2_655 . . . ? C14 C9 N10 C11 0.0(3) . . . . ? C1 C9 N10 C11 179.86(16) . . . . ? C9 N10 C11 C12 0.8(3) . . . . ? N10 C11 C12 C13 -0.8(3) . . . . ? C11 C12 C13 C14 -0.1(3) . . . . ? N10 C9 C14 C13 -0.7(3) . . . . ? C1 C9 C14 C13 179.38(17) . . . . ? C12 C13 C14 C9 0.8(3) . . . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 25.40 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.376 _refine_diff_density_min -0.231 _refine_diff_density_rms 0.042 # Attachment '- cif_6.txt' data_6 _database_code_depnum_ccdc_archive 'CCDC 832893' #TrackingRef '- cif_6.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C28 H20 F22' _chemical_formula_sum 'C28 H20 F22' _chemical_formula_weight 774.44 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M Pc _symmetry_space_group_name_Hall 'P -2yc ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x, -y, z+1/2' _cell_length_a 12.266(6) _cell_length_b 22.489(2) _cell_length_c 10.538(5) _cell_angle_alpha 90.00 _cell_angle_beta 95.81(1) _cell_angle_gamma 90.00 _cell_volume 2892(3) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 4668 _cell_measurement_theta_min 2.66 _cell_measurement_theta_max 24.39 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.06 _exptl_crystal_density_diffrn 1.779 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1544 _exptl_absorpt_coefficient_mu 0.203 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9053 _exptl_absorpt_correction_T_max 0.9879 _exptl_absorpt_process_details 'SADABS version 2.10 (Sheldrick,Bruker AXS Inc.,2002)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_device 'Bruker Kappa APEX II CCD' _diffrn_detector_area_resol_mean ? _diffrn_radiation_monochromator graphite _diffrn_measurement_method '0.5 deg frames in phi and omega' _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_radiation_wavelength_id x-ray _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 30248 _diffrn_reflns_av_R_equivalents 0.0927 _diffrn_reflns_av_sigmaI/netI 0.1106 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -28 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.67 _diffrn_reflns_theta_max 27.00 _reflns_number_total 11902 _reflns_number_gt 6346 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 v2, 1-4 (Bruker AXS, 2005-2007)' _computing_cell_refinement 'APEX2 v2, 1-4 (Bruker AXS, 2005-2007)' _computing_data_reduction 'SAINT NT v6.0 (Bruker AXS, 2003)' _computing_structure_solution 'SIR2004 (Burla et al., 2005)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997), WinGX (Farrugia 1999), PLATON (Spek 2005)' _computing_molecular_graphics 'ORTEP-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX (Farrugia 1999), enCIFer (Allen et al. 2004)' _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^)+(0.1235P)^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 0.2(8) _refine_ls_number_reflns 11902 _refine_ls_number_parameters 905 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.1328 _refine_ls_R_factor_gt 0.0796 _refine_ls_wR_factor_ref 0.2091 _refine_ls_wR_factor_gt 0.1813 _refine_ls_goodness_of_fit_ref 0.894 _refine_ls_restrained_S_all 0.894 _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 C1A C -0.2327(5) 0.8513(3) 0.9747(6) 0.0279(14) Uani 1 1 d . . . C2A C -0.3475(5) 0.8705(3) 1.0080(6) 0.0257(14) Uani 1 1 d . . . H2AA H -0.3384 0.9053 1.0657 0.031 Uiso 1 1 calc R . . H2AB H -0.3904 0.8838 0.9285 0.031 Uiso 1 1 calc R . . C3A C -0.4141(5) 0.8244(3) 1.0700(7) 0.0335(16) Uani 1 1 d . . . F1A F -0.3543(3) 0.79086(17) 1.1588(4) 0.0402(10) Uani 1 1 d . . . F2A F -0.4599(3) 0.78523(18) 0.9811(4) 0.0436(10) Uani 1 1 d . . . C4A C -0.5064(5) 0.8514(3) 1.1383(6) 0.0308(15) Uani 1 1 d . . . F3A F -0.4592(3) 0.88034(17) 1.2418(3) 0.0361(9) Uani 1 1 d . . . F4A F -0.5579(3) 0.89461(17) 1.0637(4) 0.0340(9) Uani 1 1 d . . . C5A C -0.5966(5) 0.8081(3) 1.1811(7) 0.0350(16) Uani 1 1 d . . . F5A F -0.5520(3) 0.75183(18) 1.1958(4) 0.0480(11) Uani 1 1 d . . . C6A C -0.6383(6) 0.8265(4) 1.3057(7) 0.0431(18) Uani 1 1 d . . . F6A F -0.5593(4) 0.8166(2) 1.4000(4) 0.0569(12) Uani 1 1 d . . . F7A F -0.7239(3) 0.7952(2) 1.3295(4) 0.0575(12) Uani 1 1 d . . . F8A F -0.6634(3) 0.88417(19) 1.3066(4) 0.0494(11) Uani 1 1 d . . . C7A C -0.6944(6) 0.8010(4) 1.0755(8) 0.048(2) Uani 1 1 d . . . F9A F -0.7490(4) 0.7515(2) 1.0980(5) 0.0639(14) Uani 1 1 d . . . F10A F -0.7648(3) 0.8474(2) 1.0861(5) 0.0605(13) Uani 1 1 d . . . F11A F -0.6675(3) 0.7988(2) 0.9619(4) 0.0566(12) Uani 1 1 d . . . C8A C -0.2481(5) 0.7933(3) 0.8955(7) 0.0320(15) Uani 1 1 d . . . H8AA H -0.2717 0.7612 0.9496 0.048 Uiso 1 1 calc R . . H8AB H -0.1786 0.7823 0.8636 0.048 Uiso 1 1 calc R . . H8AC H -0.3039 0.7995 0.8234 0.048 Uiso 1 1 calc R . . C9A C -0.1550(5) 0.8400(3) 1.0967(6) 0.0285(14) Uani 1 1 d . . . C10A C -0.1566(5) 0.8754(3) 1.2061(7) 0.0364(16) Uani 1 1 d . . . H10A H -0.2088 0.9066 1.2067 0.044 Uiso 1 1 calc R . . C11A C -0.0859(5) 0.8661(4) 1.3105(7) 0.0404(18) Uani 1 1 d . . . H11A H -0.0886 0.8914 1.3824 0.048 Uiso 1 1 calc R . . C12A C -0.0094(6) 0.8209(4) 1.3158(8) 0.0451(19) Uani 1 1 d . . . H12A H 0.0389 0.8142 1.3907 0.054 Uiso 1 1 calc R . . C13A C -0.0052(6) 0.7854(3) 1.2085(7) 0.0401(18) Uani 1 1 d . . . H13A H 0.0479 0.7546 1.2084 0.048 Uiso 1 1 calc R . . C14A C -0.0777(5) 0.7948(3) 1.1028(7) 0.0338(16) Uani 1 1 d . . . H14A H -0.0751 0.7695 1.0311 0.041 Uiso 1 1 calc R . . C15A C -0.1838(5) 0.9041(3) 0.8896(6) 0.0249(13) Uani 1 1 d . . . C16A C -0.0697(4) 0.8830(3) 0.8572(6) 0.0256(14) Uani 1 1 d . . . H16A H -0.0281 0.8686 0.9367 0.031 Uiso 1 1 calc R . . H16B H -0.0802 0.8487 0.7984 0.031 Uiso 1 1 calc R . . C17A C -0.0012(5) 0.9284(3) 0.7980(6) 0.0244(14) Uani 1 1 d . . . F12A F 0.0463(3) 0.96712(17) 0.8841(4) 0.0391(10) Uani 1 1 d . . . F13A F -0.0589(3) 0.96168(17) 0.7064(4) 0.0365(9) Uani 1 1 d . . . C18A C 0.0911(5) 0.8981(3) 0.7306(6) 0.0327(16) Uani 1 1 d . . . F14A F 0.0404(3) 0.87008(18) 0.6263(4) 0.0397(10) Uani 1 1 d . . . F15A F 0.1378(3) 0.85478(16) 0.8074(3) 0.0307(8) Uani 1 1 d . . . C19A C 0.1841(5) 0.9390(3) 0.6899(7) 0.0317(15) Uani 1 1 d . . . F16A F 0.1459(3) 0.99587(18) 0.6699(4) 0.0437(10) Uani 1 1 d . . . C20A C 0.2846(6) 0.9443(3) 0.7964(7) 0.0405(18) Uani 1 1 d . . . F20A F 0.3404(3) 0.9927(2) 0.7766(4) 0.0543(12) Uani 1 1 d . . . F21A F 0.2524(3) 0.94654(19) 0.9110(4) 0.0451(10) Uani 1 1 d . . . F22A F 0.3489(3) 0.89678(18) 0.7894(4) 0.0458(10) Uani 1 1 d . . . C21A C 0.2260(6) 0.9171(4) 0.5657(7) 0.0436(18) Uani 1 1 d . . . F17A F 0.1528(3) 0.9293(2) 0.4672(4) 0.0489(11) Uani 1 1 d . . . F18A F 0.3169(3) 0.9457(2) 0.5449(4) 0.0497(11) Uani 1 1 d . . . F19A F 0.2439(3) 0.85905(19) 0.5677(4) 0.0452(10) Uani 1 1 d . . . C22A C -0.1700(5) 0.9614(3) 0.9656(6) 0.0299(15) Uani 1 1 d . . . H22A H -0.1465 0.9932 0.9110 0.045 Uiso 1 1 calc R . . H22B H -0.1147 0.9557 1.0384 0.045 Uiso 1 1 calc R . . H22C H -0.2400 0.9723 0.9966 0.045 Uiso 1 1 calc R . . C23A C -0.2615(5) 0.9135(3) 0.7674(6) 0.0275(14) Uani 1 1 d . . . C24A C -0.2583(5) 0.8783(3) 0.6600(6) 0.0339(15) Uani 1 1 d . . . H24A H -0.2052 0.8475 0.6610 0.041 Uiso 1 1 calc R . . C25A C -0.3309(6) 0.8866(3) 0.5496(7) 0.0407(18) Uani 1 1 d . . . H25A H -0.3265 0.8619 0.4772 0.049 Uiso 1 1 calc R . . C26A C -0.4089(5) 0.9310(4) 0.5475(7) 0.0405(18) Uani 1 1 d . . . H26A H -0.4593 0.9365 0.4739 0.049 Uiso 1 1 calc R . . C27A C -0.4134(5) 0.9666(3) 0.6500(7) 0.0332(16) Uani 1 1 d . . . H27A H -0.4668 0.9972 0.6482 0.040 Uiso 1 1 calc R . . C28A C -0.3392(5) 0.9585(3) 0.7597(7) 0.0312(15) Uani 1 1 d . . . H28A H -0.3424 0.9846 0.8301 0.037 Uiso 1 1 calc R . . C1B C 0.7704(5) 0.6546(3) 0.4924(7) 0.0332(16) Uani 1 1 d . . . C2B C 0.6573(5) 0.6300(3) 0.5219(7) 0.0302(15) Uani 1 1 d . . . H2BA H 0.6172 0.6168 0.4405 0.036 Uiso 1 1 calc R . . H2BB H 0.6704 0.5943 0.5763 0.036 Uiso 1 1 calc R . . C3B C 0.5836(5) 0.6714(3) 0.5867(7) 0.0323(15) Uani 1 1 d . . . F1B F 0.6367(3) 0.70823(17) 0.6743(4) 0.0365(9) Uani 1 1 d . . . F2B F 0.5294(3) 0.70900(17) 0.4974(4) 0.0401(10) Uani 1 1 d . . . C4B C 0.4969(5) 0.6392(3) 0.6547(6) 0.0298(15) Uani 1 1 d . . . F3B F 0.5523(3) 0.60349(18) 0.7419(3) 0.0392(9) Uani 1 1 d . . . F4B F 0.4395(3) 0.60352(17) 0.5704(4) 0.0365(9) Uani 1 1 d . . . C5B C 0.4141(5) 0.6733(3) 0.7291(7) 0.0346(16) Uani 1 1 d . . . F5B F 0.4711(3) 0.69253(19) 0.8425(4) 0.0450(10) Uani 1 1 d . . . C6B C 0.3239(5) 0.6311(4) 0.7737(7) 0.0428(18) Uani 1 1 d . . . F6B F 0.2795(4) 0.6547(2) 0.8689(4) 0.0616(13) Uani 1 1 d . . . F7B F 0.3624(3) 0.5791(2) 0.8051(4) 0.0533(11) Uani 1 1 d . . . F8B F 0.2450(3) 0.6259(2) 0.6736(5) 0.0548(12) Uani 1 1 d . . . C7B C 0.3624(6) 0.7296(3) 0.6646(7) 0.0424(17) Uani 1 1 d . . . F9B F 0.2807(3) 0.74921(18) 0.7254(4) 0.0524(11) Uani 1 1 d . . . F10B F 0.3228(3) 0.7174(2) 0.5437(4) 0.0466(10) Uani 1 1 d . . . F11B F 0.4357(3) 0.77299(19) 0.6661(4) 0.0500(11) Uani 1 1 d . . . C8B C 0.7466(6) 0.7145(3) 0.4192(7) 0.0381(17) Uani 1 1 d . . . H8BA H 0.7302 0.7456 0.4797 0.057 Uiso 1 1 calc R . . H8BB H 0.6836 0.7094 0.3551 0.057 Uiso 1 1 calc R . . H8BC H 0.8110 0.7261 0.3770 0.057 Uiso 1 1 calc R . . C9B C 0.8463(5) 0.6646(3) 0.6137(7) 0.0312(15) Uani 1 1 d . . . C10B C 0.8441(6) 0.6286(4) 0.7232(7) 0.0418(18) Uani 1 1 d . . . H10B H 0.7907 0.5980 0.7229 0.050 Uiso 1 1 calc R . . C11B C 0.9151(6) 0.6361(4) 0.8282(8) 0.053(2) Uani 1 1 d . . . H11B H 0.9113 0.6106 0.8995 0.063 Uiso 1 1 calc R . . C12B C 0.9938(6) 0.6807(4) 0.8333(8) 0.048(2) Uani 1 1 d . . . H12B H 1.0434 0.6860 0.9077 0.058 Uiso 1 1 calc R . . C13B C 0.9989(6) 0.7173(4) 0.7286(8) 0.047(2) Uani 1 1 d . . . H13B H 1.0527 0.7477 0.7307 0.056 Uiso 1 1 calc R . . C14B C 0.9251(5) 0.7098(3) 0.6194(7) 0.0370(17) Uani 1 1 d . . . H14B H 0.9286 0.7356 0.5485 0.044 Uiso 1 1 calc R . . C15B C 0.8221(5) 0.6053(3) 0.4020(6) 0.0315(15) Uani 1 1 d . . . C16B C 0.9339(5) 0.6294(3) 0.3736(6) 0.0331(16) Uani 1 1 d . . . H16C H 0.9230 0.6711 0.3450 0.040 Uiso 1 1 calc R . . H16D H 0.9814 0.6305 0.4553 0.040 Uiso 1 1 calc R . . C17B C 0.9965(6) 0.5984(4) 0.2781(8) 0.047(2) Uani 1 1 d . . . F12B F 0.9668(3) 0.6243(2) 0.1560(4) 0.0619(13) Uani 1 1 d . . . F13B F 0.9734(4) 0.5416(2) 0.2625(5) 0.0638(14) Uani 1 1 d . . . C18B C 1.1185(5) 0.6100(4) 0.2988(7) 0.0417(18) Uani 1 1 d . . . F14B F 1.1555(3) 0.5780(2) 0.4056(4) 0.0538(11) Uani 1 1 d . . . F15B F 1.1362(3) 0.6668(2) 0.3256(4) 0.0447(10) Uani 1 1 d . . . C19B C 1.1950(5) 0.5924(4) 0.1945(7) 0.0456(19) Uani 1 1 d . . . F16B F 1.1746(3) 0.6364(2) 0.0996(4) 0.0539(11) Uani 1 1 d . . . C20B C 1.1734(6) 0.5329(5) 0.1308(10) 0.062(3) Uani 1 1 d . . . F20B F 1.0821(4) 0.5347(3) 0.0508(5) 0.0798(17) Uani 1 1 d . . . F21B F 1.2557(4) 0.5179(2) 0.0620(6) 0.0816(18) Uani 1 1 d . . . F22B F 1.1623(4) 0.4908(2) 0.2134(6) 0.0753(16) Uani 1 1 d . . . C21B C 1.3188(6) 0.6001(4) 0.2450(8) 0.050(2) Uani 1 1 d . . . F17B F 1.3511(4) 0.5507(2) 0.3056(6) 0.0752(15) Uani 1 1 d . . . F18B F 1.3745(4) 0.6073(3) 0.1463(5) 0.0727(15) Uani 1 1 d . . . F19B F 1.3360(3) 0.6459(2) 0.3207(4) 0.0556(12) Uani 1 1 d . . . C22B C 0.8409(6) 0.5463(3) 0.4779(7) 0.0374(17) Uani 1 1 d . . . H22D H 0.8681 0.5158 0.4226 0.056 Uiso 1 1 calc R . . H22E H 0.7716 0.5331 0.5073 0.056 Uiso 1 1 calc R . . H22F H 0.8950 0.5529 0.5516 0.056 Uiso 1 1 calc R . . C23B C 0.7464(5) 0.5952(3) 0.2800(7) 0.0326(16) Uani 1 1 d . . . C24B C 0.7420(5) 0.6346(3) 0.1778(7) 0.0370(16) Uani 1 1 d . . . H24B H 0.7882 0.6686 0.1842 0.044 Uiso 1 1 calc R . . C25B C 0.6725(6) 0.6261(4) 0.0664(8) 0.0455(19) Uani 1 1 d . . . H25B H 0.6720 0.6537 -0.0019 0.055 Uiso 1 1 calc R . . C26B C 0.6043(5) 0.5772(3) 0.0562(7) 0.0411(18) Uani 1 1 d . . . H26B H 0.5554 0.5714 -0.0186 0.049 Uiso 1 1 calc R . . C27B C 0.6071(6) 0.5373(3) 0.1529(7) 0.0383(17) Uani 1 1 d . . . H27B H 0.5603 0.5035 0.1451 0.046 Uiso 1 1 calc R . . C28B C 0.6781(5) 0.5453(3) 0.2638(7) 0.0336(16) Uani 1 1 d . . . H28B H 0.6801 0.5163 0.3296 0.040 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1A 0.032(3) 0.026(4) 0.027(3) -0.006(3) 0.007(3) -0.007(3) C2A 0.027(3) 0.026(4) 0.025(3) -0.001(3) 0.003(2) -0.004(3) C3A 0.030(3) 0.030(4) 0.040(4) 0.000(3) 0.001(3) -0.002(3) F1A 0.038(2) 0.034(2) 0.050(3) 0.0144(19) 0.0098(18) 0.0025(17) F2A 0.045(2) 0.044(3) 0.044(2) -0.019(2) 0.0167(18) -0.0175(18) C4A 0.028(3) 0.032(4) 0.032(4) 0.002(3) 0.004(3) -0.004(3) F3A 0.0396(19) 0.046(2) 0.0230(19) -0.0092(18) 0.0058(16) -0.0080(17) F4A 0.0274(17) 0.035(2) 0.040(2) 0.0060(18) 0.0084(16) 0.0014(16) C5A 0.036(3) 0.034(4) 0.036(4) 0.005(3) 0.007(3) 0.000(3) F5A 0.046(2) 0.038(3) 0.063(3) 0.011(2) 0.021(2) -0.0003(19) C6A 0.043(4) 0.052(5) 0.037(4) -0.003(4) 0.018(3) -0.003(4) F6A 0.067(3) 0.068(3) 0.035(2) 0.009(2) 0.000(2) -0.007(2) F7A 0.051(3) 0.080(4) 0.046(3) 0.007(2) 0.022(2) -0.015(2) F8A 0.061(3) 0.043(3) 0.048(3) -0.002(2) 0.022(2) 0.010(2) C7A 0.034(4) 0.061(6) 0.049(5) 0.011(4) 0.002(3) -0.017(4) F9A 0.060(3) 0.055(3) 0.077(4) -0.004(3) 0.010(3) -0.031(2) F10A 0.038(2) 0.078(4) 0.066(3) 0.012(3) 0.007(2) 0.002(2) F11A 0.050(2) 0.076(4) 0.043(3) -0.011(2) 0.000(2) -0.018(2) C8A 0.035(3) 0.029(4) 0.033(4) -0.010(3) 0.009(3) -0.006(3) C9A 0.029(3) 0.031(4) 0.027(3) 0.003(3) 0.007(3) 0.000(3) C10A 0.031(3) 0.039(4) 0.038(4) -0.005(3) -0.001(3) 0.002(3) C11A 0.042(4) 0.053(5) 0.025(4) -0.002(3) -0.002(3) 0.002(3) C12A 0.046(4) 0.047(5) 0.041(5) 0.012(4) -0.003(3) -0.003(4) C13A 0.038(4) 0.038(5) 0.045(5) 0.020(4) 0.009(3) 0.012(3) C14A 0.039(3) 0.031(4) 0.033(4) 0.004(3) 0.013(3) 0.002(3) C15A 0.027(3) 0.026(4) 0.022(3) 0.001(3) 0.003(2) 0.004(3) C16A 0.027(3) 0.021(3) 0.029(3) 0.000(3) 0.004(3) 0.002(3) C17A 0.022(3) 0.029(4) 0.022(3) -0.001(3) 0.003(2) 0.000(3) F12A 0.039(2) 0.038(2) 0.042(2) -0.0114(19) 0.0119(18) -0.0042(17) F13A 0.0319(18) 0.036(2) 0.043(2) 0.0111(19) 0.0084(17) 0.0072(16) C18A 0.032(3) 0.033(4) 0.033(4) -0.010(3) 0.003(3) 0.003(3) F14A 0.039(2) 0.048(3) 0.032(2) -0.0122(19) 0.0012(17) -0.0020(18) F15A 0.0287(17) 0.030(2) 0.034(2) 0.0093(17) 0.0024(15) 0.0013(15) C19A 0.031(3) 0.026(4) 0.040(4) 0.008(3) 0.012(3) 0.004(3) F16A 0.041(2) 0.034(3) 0.057(3) 0.012(2) 0.0134(19) 0.0026(17) C20A 0.041(4) 0.045(5) 0.034(4) 0.000(3) 0.000(3) -0.011(4) F20A 0.045(2) 0.051(3) 0.068(3) -0.007(2) 0.011(2) -0.018(2) F21A 0.044(2) 0.060(3) 0.031(2) -0.008(2) 0.0038(18) -0.002(2) F22A 0.0318(19) 0.051(3) 0.054(3) 0.003(2) -0.0009(18) 0.0108(19) C21A 0.036(4) 0.053(6) 0.041(4) 0.000(4) 0.003(3) 0.000(3) F17A 0.052(2) 0.059(3) 0.036(2) 0.005(2) 0.0072(19) 0.008(2) F18A 0.041(2) 0.063(3) 0.049(3) 0.011(2) 0.021(2) 0.002(2) F19A 0.053(2) 0.046(3) 0.039(2) 0.004(2) 0.0145(19) 0.013(2) C22A 0.032(3) 0.034(4) 0.024(3) -0.006(3) 0.004(3) -0.005(3) C23A 0.020(3) 0.031(4) 0.031(4) -0.005(3) 0.006(3) -0.005(3) C24A 0.038(3) 0.032(4) 0.032(4) -0.004(3) 0.005(3) -0.001(3) C25A 0.042(4) 0.049(5) 0.030(4) -0.004(3) -0.002(3) -0.006(3) C26A 0.026(3) 0.065(5) 0.030(4) 0.009(4) -0.001(3) -0.009(3) C27A 0.029(3) 0.032(4) 0.038(4) 0.006(3) 0.005(3) -0.001(3) C28A 0.031(3) 0.031(4) 0.032(4) 0.007(3) 0.010(3) 0.001(3) C1B 0.031(3) 0.028(4) 0.042(4) 0.009(3) 0.008(3) 0.002(3) C2B 0.028(3) 0.032(4) 0.031(4) -0.001(3) 0.007(3) 0.001(3) C3B 0.033(3) 0.032(4) 0.032(4) -0.003(3) 0.004(3) -0.003(3) F1B 0.0336(19) 0.035(2) 0.041(2) -0.0103(19) 0.0054(16) -0.0037(16) F2B 0.0370(19) 0.045(3) 0.039(2) 0.0096(19) 0.0062(17) 0.0135(17) C4B 0.028(3) 0.031(4) 0.029(4) -0.011(3) -0.003(3) 0.003(3) F3B 0.0382(19) 0.049(3) 0.030(2) 0.0040(19) 0.0029(16) -0.0001(18) F4B 0.0379(19) 0.034(2) 0.038(2) -0.0097(18) 0.0081(17) -0.0074(16) C5B 0.038(3) 0.033(4) 0.035(4) -0.004(3) 0.008(3) -0.006(3) F5B 0.049(2) 0.052(3) 0.032(2) -0.0121(19) -0.0045(18) 0.0045(19) C6B 0.035(3) 0.055(5) 0.040(4) -0.012(4) 0.011(3) -0.002(3) F6B 0.059(3) 0.077(3) 0.054(3) -0.011(2) 0.029(2) -0.003(2) F7B 0.052(2) 0.052(3) 0.059(3) 0.015(2) 0.019(2) -0.003(2) F8B 0.038(2) 0.060(3) 0.065(3) -0.005(2) 0.002(2) -0.013(2) C7B 0.045(4) 0.045(5) 0.038(4) -0.010(4) 0.009(3) 0.000(4) F9B 0.058(2) 0.046(3) 0.057(3) 0.001(2) 0.026(2) 0.016(2) F10B 0.042(2) 0.058(3) 0.039(2) 0.005(2) 0.0011(18) 0.0107(19) F11B 0.052(2) 0.040(3) 0.061(3) -0.004(2) 0.016(2) 0.003(2) C8B 0.036(3) 0.038(4) 0.042(4) 0.005(3) 0.009(3) -0.001(3) C9B 0.026(3) 0.033(4) 0.035(4) -0.001(3) 0.006(3) 0.002(3) C10B 0.036(4) 0.049(5) 0.039(4) 0.009(4) -0.001(3) -0.001(3) C11B 0.054(5) 0.050(5) 0.053(5) -0.003(4) -0.002(4) 0.010(4) C12B 0.040(4) 0.064(6) 0.039(5) -0.021(4) -0.005(3) 0.009(4) C13B 0.030(3) 0.052(5) 0.059(5) -0.018(4) 0.004(3) -0.001(3) C14B 0.028(3) 0.038(4) 0.045(4) -0.001(3) 0.006(3) 0.000(3) C15B 0.032(3) 0.034(4) 0.030(4) 0.001(3) 0.006(3) 0.003(3) C16B 0.037(3) 0.036(4) 0.027(4) -0.001(3) 0.007(3) 0.004(3) C17B 0.034(3) 0.064(6) 0.044(5) -0.011(4) 0.010(3) -0.002(4) F12B 0.051(2) 0.101(4) 0.034(2) -0.001(2) 0.0021(19) 0.012(2) F13B 0.060(3) 0.039(3) 0.100(4) -0.021(3) 0.043(3) -0.014(2) C18B 0.037(3) 0.045(5) 0.045(4) 0.008(4) 0.009(3) 0.008(3) F14B 0.056(2) 0.065(3) 0.040(2) 0.016(2) 0.005(2) 0.008(2) F15B 0.041(2) 0.046(3) 0.047(3) -0.001(2) 0.0036(18) 0.0009(19) C19B 0.036(3) 0.060(5) 0.042(4) -0.006(4) 0.008(3) 0.000(3) F16B 0.055(2) 0.068(3) 0.039(2) 0.007(2) 0.006(2) -0.002(2) C20B 0.039(4) 0.075(7) 0.072(6) -0.027(6) 0.006(4) 0.007(4) F20B 0.058(3) 0.105(4) 0.077(4) -0.049(3) 0.008(3) -0.002(3) F21B 0.061(3) 0.091(4) 0.098(4) -0.051(3) 0.035(3) 0.000(3) F22B 0.078(3) 0.039(3) 0.115(5) -0.009(3) 0.037(3) 0.003(2) C21B 0.046(4) 0.042(5) 0.063(5) -0.011(4) 0.020(4) 0.009(4) F17B 0.062(3) 0.075(4) 0.087(4) 0.012(3) 0.000(3) 0.020(3) F18B 0.049(3) 0.107(4) 0.065(3) -0.018(3) 0.022(2) -0.006(3) F19B 0.043(2) 0.072(3) 0.052(3) -0.017(2) 0.003(2) -0.008(2) C22B 0.046(4) 0.032(4) 0.036(4) 0.007(3) 0.014(3) 0.011(3) C23B 0.031(3) 0.034(4) 0.034(4) 0.006(3) 0.010(3) 0.008(3) C24B 0.035(3) 0.036(4) 0.039(4) 0.005(3) 0.001(3) -0.007(3) C25B 0.044(4) 0.050(5) 0.043(5) 0.011(4) 0.005(3) 0.000(4) C26B 0.034(4) 0.046(5) 0.042(4) -0.004(4) -0.003(3) 0.006(3) C27B 0.040(4) 0.030(4) 0.046(5) 0.000(3) 0.012(3) 0.002(3) C28B 0.035(3) 0.031(4) 0.036(4) 0.001(3) 0.010(3) -0.002(3) _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 C1A C9A 1.542(9) . ? C1A C2A 1.547(8) . ? C1A C8A 1.551(9) . ? C1A C15A 1.637(8) . ? C2A C3A 1.508(9) . ? C2A H2AA 0.9900 . ? C2A H2AB 0.9900 . ? C3A F1A 1.358(8) . ? C3A F2A 1.364(8) . ? C3A C4A 1.527(9) . ? C4A F3A 1.350(7) . ? C4A F4A 1.365(7) . ? C4A C5A 1.574(9) . ? C5A F5A 1.380(8) . ? C5A C6A 1.515(10) . ? C5A C7A 1.559(10) . ? C6A F7A 1.309(8) . ? C6A F8A 1.332(9) . ? C6A F6A 1.334(9) . ? C7A F11A 1.276(9) . ? C7A F9A 1.333(8) . ? C7A F10A 1.365(9) . ? C8A H8AA 0.9800 . ? C8A H8AB 0.9800 . ? C8A H8AC 0.9800 . ? C9A C14A 1.387(9) . ? C9A C10A 1.403(10) . ? C10A C11A 1.346(10) . ? C10A H10A 0.9500 . ? C11A C12A 1.380(10) . ? C11A H11A 0.9500 . ? C12A C13A 1.390(11) . ? C12A H12A 0.9500 . ? C13A C14A 1.370(10) . ? C13A H13A 0.9500 . ? C14A H14A 0.9500 . ? C15A C22A 1.518(9) . ? C15A C23A 1.538(9) . ? C15A C16A 1.549(8) . ? C16A C17A 1.498(9) . ? C16A H16A 0.9900 . ? C16A H16B 0.9900 . ? C17A F12A 1.347(7) . ? C17A F13A 1.362(7) . ? C17A C18A 1.553(8) . ? C18A F15A 1.356(8) . ? C18A F14A 1.363(7) . ? C18A C19A 1.558(9) . ? C19A F16A 1.371(8) . ? C19A C21A 1.535(10) . ? C19A C20A 1.585(10) . ? C20A F21A 1.310(8) . ? C20A F20A 1.313(8) . ? C20A F22A 1.335(8) . ? C21A F19A 1.324(9) . ? C21A F18A 1.325(8) . ? C21A F17A 1.330(8) . ? C22A H22A 0.9800 . ? C22A H22B 0.9800 . ? C22A H22C 0.9800 . ? C23A C28A 1.386(9) . ? C23A C24A 1.386(9) . ? C24A C25A 1.404(10) . ? C24A H24A 0.9500 . ? C25A C26A 1.381(11) . ? C25A H25A 0.9500 . ? C26A C27A 1.351(10) . ? C26A H26A 0.9500 . ? C27A C28A 1.408(9) . ? C27A H27A 0.9500 . ? C28A H28A 0.9500 . ? C1B C9B 1.520(10) . ? C1B C2B 1.553(9) . ? C1B C8B 1.566(9) . ? C1B C15B 1.632(9) . ? C2B C3B 1.509(9) . ? C2B H2BA 0.9900 . ? C2B H2BB 0.9900 . ? C3B F1B 1.357(8) . ? C3B F2B 1.384(8) . ? C3B C4B 1.524(9) . ? C4B F4B 1.343(7) . ? C4B F3B 1.352(7) . ? C4B C5B 1.547(9) . ? C5B F5B 1.391(8) . ? C5B C7B 1.543(10) . ? C5B C6B 1.566(10) . ? C6B F7B 1.292(9) . ? C6B F6B 1.302(8) . ? C6B F8B 1.362(8) . ? C7B F9B 1.318(8) . ? C7B F11B 1.326(8) . ? C7B F10B 1.345(8) . ? C8B H8BA 0.9800 . ? C8B H8BB 0.9800 . ? C8B H8BC 0.9800 . ? C9B C14B 1.398(9) . ? C9B C10B 1.413(10) . ? C10B C11B 1.347(11) . ? C10B H10B 0.9500 . ? C11B C12B 1.390(11) . ? C11B H11B 0.9500 . ? C12B C13B 1.383(12) . ? C12B H12B 0.9500 . ? C13B C14B 1.400(11) . ? C13B H13B 0.9500 . ? C14B H14B 0.9500 . ? C15B C23B 1.525(10) . ? C15B C16B 1.532(9) . ? C15B C22B 1.553(9) . ? C16B C17B 1.498(10) . ? C16B H16C 0.9900 . ? C16B H16D 0.9900 . ? C17B F13B 1.316(9) . ? C17B F12B 1.426(9) . ? C17B C18B 1.513(10) . ? C18B F15B 1.321(8) . ? C18B F14B 1.373(8) . ? C18B C19B 1.567(10) . ? C19B F16B 1.411(9) . ? C19B C20B 1.508(12) . ? C19B C21B 1.567(10) . ? C20B F22B 1.302(11) . ? C20B F20B 1.333(10) . ? C20B F21B 1.344(9) . ? C21B F19B 1.308(9) . ? C21B F18B 1.311(9) . ? C21B F17B 1.321(9) . ? C22B H22D 0.9800 . ? C22B H22E 0.9800 . ? C22B H22F 0.9800 . ? C23B C24B 1.391(10) . ? C23B C28B 1.402(9) . ? C24B C25B 1.393(10) . ? C24B H24B 0.9500 . ? C25B C26B 1.380(10) . ? C25B H25B 0.9500 . ? C26B C27B 1.355(10) . ? C26B H26B 0.9500 . ? C27B C28B 1.397(10) . ? C27B H27B 0.9500 . ? C28B H28B 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 C9A C1A C2A 110.9(5) . . ? C9A C1A C8A 110.0(5) . . ? C2A C1A C8A 107.0(5) . . ? C9A C1A C15A 110.2(4) . . ? C2A C1A C15A 108.4(5) . . ? C8A C1A C15A 110.3(5) . . ? C3A C2A C1A 116.9(5) . . ? C3A C2A H2AA 108.1 . . ? C1A C2A H2AA 108.1 . . ? C3A C2A H2AB 108.1 . . ? C1A C2A H2AB 108.1 . . ? H2AA C2A H2AB 107.3 . . ? F1A C3A F2A 105.7(5) . . ? F1A C3A C2A 113.6(5) . . ? F2A C3A C2A 110.5(6) . . ? F1A C3A C4A 105.7(5) . . ? F2A C3A C4A 107.9(5) . . ? C2A C3A C4A 113.0(5) . . ? F3A C4A F4A 104.9(5) . . ? F3A C4A C3A 107.2(5) . . ? F4A C4A C3A 109.5(5) . . ? F3A C4A C5A 108.9(5) . . ? F4A C4A C5A 107.9(5) . . ? C3A C4A C5A 117.7(6) . . ? F5A C5A C6A 108.6(6) . . ? F5A C5A C7A 104.8(6) . . ? C6A C5A C7A 110.1(6) . . ? F5A C5A C4A 108.5(5) . . ? C6A C5A C4A 112.8(6) . . ? C7A C5A C4A 111.8(6) . . ? F7A C6A F8A 109.3(6) . . ? F7A C6A F6A 107.6(6) . . ? F8A C6A F6A 108.0(6) . . ? F7A C6A C5A 111.5(6) . . ? F8A C6A C5A 111.8(6) . . ? F6A C6A C5A 108.4(6) . . ? F11A C7A F9A 108.4(7) . . ? F11A C7A F10A 109.4(7) . . ? F9A C7A F10A 106.9(6) . . ? F11A C7A C5A 114.9(6) . . ? F9A C7A C5A 108.8(6) . . ? F10A C7A C5A 108.2(7) . . ? C1A C8A H8AA 109.5 . . ? C1A C8A H8AB 109.5 . . ? H8AA C8A H8AB 109.5 . . ? C1A C8A H8AC 109.5 . . ? H8AA C8A H8AC 109.5 . . ? H8AB C8A H8AC 109.5 . . ? C14A C9A C10A 116.3(6) . . ? C14A C9A C1A 121.4(6) . . ? C10A C9A C1A 122.3(6) . . ? C11A C10A C9A 121.5(7) . . ? C11A C10A H10A 119.2 . . ? C9A C10A H10A 119.2 . . ? C10A C11A C12A 121.7(7) . . ? C10A C11A H11A 119.1 . . ? C12A C11A H11A 119.1 . . ? C11A C12A C13A 118.2(7) . . ? C11A C12A H12A 120.9 . . ? C13A C12A H12A 120.9 . . ? C14A C13A C12A 119.8(7) . . ? C14A C13A H13A 120.1 . . ? C12A C13A H13A 120.1 . . ? C13A C14A C9A 122.5(7) . . ? C13A C14A H14A 118.8 . . ? C9A C14A H14A 118.8 . . ? C22A C15A C23A 110.6(5) . . ? C22A C15A C16A 108.8(5) . . ? C23A C15A C16A 110.8(5) . . ? C22A C15A C1A 110.7(5) . . ? C23A C15A C1A 109.2(4) . . ? C16A C15A C1A 106.7(5) . . ? C17A C16A C15A 116.1(5) . . ? C17A C16A H16A 108.3 . . ? C15A C16A H16A 108.3 . . ? C17A C16A H16B 108.3 . . ? C15A C16A H16B 108.3 . . ? H16A C16A H16B 107.4 . . ? F12A C17A F13A 106.3(5) . . ? F12A C17A C16A 112.5(5) . . ? F13A C17A C16A 113.4(5) . . ? F12A C17A C18A 107.8(5) . . ? F13A C17A C18A 105.5(5) . . ? C16A C17A C18A 110.9(5) . . ? F15A C18A F14A 106.2(5) . . ? F15A C18A C17A 109.0(5) . . ? F14A C18A C17A 106.1(5) . . ? F15A C18A C19A 108.2(5) . . ? F14A C18A C19A 109.8(5) . . ? C17A C18A C19A 117.1(6) . . ? F16A C19A C21A 107.8(6) . . ? F16A C19A C18A 110.2(5) . . ? C21A C19A C18A 111.3(6) . . ? F16A C19A C20A 105.6(6) . . ? C21A C19A C20A 108.9(5) . . ? C18A C19A C20A 112.8(5) . . ? F21A C20A F20A 109.0(6) . . ? F21A C20A F22A 108.5(6) . . ? F20A C20A F22A 109.6(6) . . ? F21A C20A C19A 111.7(5) . . ? F20A C20A C19A 109.3(6) . . ? F22A C20A C19A 108.8(6) . . ? F19A C21A F18A 109.9(6) . . ? F19A C21A F17A 108.2(6) . . ? F18A C21A F17A 106.5(6) . . ? F19A C21A C19A 111.9(6) . . ? F18A C21A C19A 110.2(6) . . ? F17A C21A C19A 110.0(6) . . ? C15A C22A H22A 109.5 . . ? C15A C22A H22B 109.5 . . ? H22A C22A H22B 109.5 . . ? C15A C22A H22C 109.5 . . ? H22A C22A H22C 109.5 . . ? H22B C22A H22C 109.5 . . ? C28A C23A C24A 116.5(6) . . ? C28A C23A C15A 120.9(6) . . ? C24A C23A C15A 122.6(6) . . ? C23A C24A C25A 122.1(7) . . ? C23A C24A H24A 118.9 . . ? C25A C24A H24A 118.9 . . ? C26A C25A C24A 119.3(7) . . ? C26A C25A H25A 120.3 . . ? C24A C25A H25A 120.3 . . ? C27A C26A C25A 120.0(7) . . ? C27A C26A H26A 120.0 . . ? C25A C26A H26A 120.0 . . ? C26A C27A C28A 120.3(6) . . ? C26A C27A H27A 119.8 . . ? C28A C27A H27A 119.8 . . ? C23A C28A C27A 121.7(7) . . ? C23A C28A H28A 119.2 . . ? C27A C28A H28A 119.2 . . ? C9B C1B C2B 111.6(6) . . ? C9B C1B C8B 110.7(6) . . ? C2B C1B C8B 106.2(5) . . ? C9B C1B C15B 110.5(5) . . ? C2B C1B C15B 106.5(5) . . ? C8B C1B C15B 111.2(5) . . ? C3B C2B C1B 117.3(6) . . ? C3B C2B H2BA 108.0 . . ? C1B C2B H2BA 108.0 . . ? C3B C2B H2BB 108.0 . . ? C1B C2B H2BB 108.0 . . ? H2BA C2B H2BB 107.2 . . ? F1B C3B F2B 104.8(5) . . ? F1B C3B C2B 114.6(5) . . ? F2B C3B C2B 109.8(5) . . ? F1B C3B C4B 106.3(5) . . ? F2B C3B C4B 107.4(5) . . ? C2B C3B C4B 113.5(5) . . ? F4B C4B F3B 106.7(5) . . ? F4B C4B C3B 108.5(5) . . ? F3B C4B C3B 106.0(5) . . ? F4B C4B C5B 107.7(5) . . ? F3B C4B C5B 105.1(5) . . ? C3B C4B C5B 121.9(6) . . ? F5B C5B C7B 105.8(5) . . ? F5B C5B C4B 106.9(5) . . ? C7B C5B C4B 116.4(6) . . ? F5B C5B C6B 103.8(5) . . ? C7B C5B C6B 111.0(6) . . ? C4B C5B C6B 111.9(6) . . ? F7B C6B F6B 110.0(7) . . ? F7B C6B F8B 109.4(6) . . ? F6B C6B F8B 108.2(6) . . ? F7B C6B C5B 112.0(5) . . ? F6B C6B C5B 110.4(6) . . ? F8B C6B C5B 106.7(6) . . ? F9B C7B F11B 107.2(6) . . ? F9B C7B F10B 108.0(6) . . ? F11B C7B F10B 110.0(6) . . ? F9B C7B C5B 111.0(6) . . ? F11B C7B C5B 110.5(6) . . ? F10B C7B C5B 110.0(6) . . ? C1B C8B H8BA 109.5 . . ? C1B C8B H8BB 109.5 . . ? H8BA C8B H8BB 109.5 . . ? C1B C8B H8BC 109.5 . . ? H8BA C8B H8BC 109.5 . . ? H8BB C8B H8BC 109.5 . . ? C14B C9B C10B 116.9(6) . . ? C14B C9B C1B 120.4(6) . . ? C10B C9B C1B 122.7(6) . . ? C11B C10B C9B 122.3(7) . . ? C11B C10B H10B 118.9 . . ? C9B C10B H10B 118.9 . . ? C10B C11B C12B 120.8(8) . . ? C10B C11B H11B 119.6 . . ? C12B C11B H11B 119.6 . . ? C13B C12B C11B 119.0(7) . . ? C13B C12B H12B 120.5 . . ? C11B C12B H12B 120.5 . . ? C12B C13B C14B 120.5(7) . . ? C12B C13B H13B 119.8 . . ? C14B C13B H13B 119.8 . . ? C9B C14B C13B 120.6(7) . . ? C9B C14B H14B 119.7 . . ? C13B C14B H14B 119.7 . . ? C23B C15B C16B 111.6(5) . . ? C23B C15B C22B 110.7(6) . . ? C16B C15B C22B 108.3(5) . . ? C23B C15B C1B 110.7(5) . . ? C16B C15B C1B 106.4(5) . . ? C22B C15B C1B 109.0(5) . . ? C17B C16B C15B 119.7(6) . . ? C17B C16B H16C 107.4 . . ? C15B C16B H16C 107.4 . . ? C17B C16B H16D 107.4 . . ? C15B C16B H16D 107.4 . . ? H16C C16B H16D 106.9 . . ? F13B C17B F12B 104.6(6) . . ? F13B C17B C16B 114.7(6) . . ? F12B C17B C16B 108.3(6) . . ? F13B C17B C18B 112.5(6) . . ? F12B C17B C18B 102.6(6) . . ? C16B C17B C18B 112.9(6) . . ? F15B C18B F14B 107.3(6) . . ? F15B C18B C17B 109.6(6) . . ? F14B C18B C17B 105.6(6) . . ? F15B C18B C19B 107.2(6) . . ? F14B C18B C19B 105.7(5) . . ? C17B C18B C19B 120.6(7) . . ? F16B C19B C20B 107.2(7) . . ? F16B C19B C21B 105.1(6) . . ? C20B C19B C21B 111.7(6) . . ? F16B C19B C18B 104.2(6) . . ? C20B C19B C18B 116.4(7) . . ? C21B C19B C18B 111.3(6) . . ? F22B C20B F20B 107.9(8) . . ? F22B C20B F21B 108.3(8) . . ? F20B C20B F21B 107.2(7) . . ? F22B C20B C19B 111.9(8) . . ? F20B C20B C19B 110.7(7) . . ? F21B C20B C19B 110.8(7) . . ? F19B C21B F18B 108.8(7) . . ? F19B C21B F17B 110.2(7) . . ? F18B C21B F17B 109.5(6) . . ? F19B C21B C19B 112.6(6) . . ? F18B C21B C19B 108.0(7) . . ? F17B C21B C19B 107.7(7) . . ? C15B C22B H22D 109.5 . . ? C15B C22B H22E 109.5 . . ? H22D C22B H22E 109.5 . . ? C15B C22B H22F 109.5 . . ? H22D C22B H22F 109.5 . . ? H22E C22B H22F 109.5 . . ? C24B C23B C28B 116.1(7) . . ? C24B C23B C15B 122.1(6) . . ? C28B C23B C15B 121.8(6) . . ? C25B C24B C23B 122.6(7) . . ? C25B C24B H24B 118.7 . . ? C23B C24B H24B 118.7 . . ? C26B C25B C24B 119.3(7) . . ? C26B C25B H25B 120.4 . . ? C24B C25B H25B 120.4 . . ? C27B C26B C25B 120.1(7) . . ? C27B C26B H26B 120.0 . . ? C25B C26B H26B 120.0 . . ? C26B C27B C28B 120.6(7) . . ? C26B C27B H27B 119.7 . . ? C28B C27B H27B 119.7 . . ? C27B C28B C23B 121.3(7) . . ? C27B C28B H28B 119.3 . . ? C23B C28B H28B 119.3 . . ? 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 C9A C1A C2A C3A -67.5(7) . . . . ? C8A C1A C2A C3A 52.4(7) . . . . ? C15A C1A C2A C3A 171.4(5) . . . . ? C1A C2A C3A F1A 40.6(8) . . . . ? C1A C2A C3A F2A -78.0(7) . . . . ? C1A C2A C3A C4A 161.0(5) . . . . ? F1A C3A C4A F3A 55.1(6) . . . . ? F2A C3A C4A F3A 167.8(5) . . . . ? C2A C3A C4A F3A -69.8(7) . . . . ? F1A C3A C4A F4A 168.3(5) . . . . ? F2A C3A C4A F4A -78.9(6) . . . . ? C2A C3A C4A F4A 43.5(7) . . . . ? F1A C3A C4A C5A -67.9(7) . . . . ? F2A C3A C4A C5A 44.8(8) . . . . ? C2A C3A C4A C5A 167.2(6) . . . . ? F3A C4A C5A F5A -97.5(6) . . . . ? F4A C4A C5A F5A 149.2(5) . . . . ? C3A C4A C5A F5A 24.7(8) . . . . ? F3A C4A C5A C6A 22.8(8) . . . . ? F4A C4A C5A C6A -90.5(7) . . . . ? C3A C4A C5A C6A 145.0(6) . . . . ? F3A C4A C5A C7A 147.5(6) . . . . ? F4A C4A C5A C7A 34.2(8) . . . . ? C3A C4A C5A C7A -90.3(7) . . . . ? F5A C5A C6A F7A -69.1(8) . . . . ? C7A C5A C6A F7A 45.0(9) . . . . ? C4A C5A C6A F7A 170.6(6) . . . . ? F5A C5A C6A F8A 168.2(5) . . . . ? C7A C5A C6A F8A -77.7(8) . . . . ? C4A C5A C6A F8A 47.9(8) . . . . ? F5A C5A C6A F6A 49.2(7) . . . . ? C7A C5A C6A F6A 163.4(6) . . . . ? C4A C5A C6A F6A -71.0(8) . . . . ? F5A C5A C7A F11A -78.5(8) . . . . ? C6A C5A C7A F11A 164.9(7) . . . . ? C4A C5A C7A F11A 38.7(9) . . . . ? F5A C5A C7A F9A 43.2(7) . . . . ? C6A C5A C7A F9A -73.4(8) . . . . ? C4A C5A C7A F9A 160.4(6) . . . . ? F5A C5A C7A F10A 158.9(5) . . . . ? C6A C5A C7A F10A 42.4(8) . . . . ? C4A C5A C7A F10A -83.8(7) . . . . ? C2A C1A C9A C14A 143.5(6) . . . . ? C8A C1A C9A C14A 25.4(8) . . . . ? C15A C1A C9A C14A -96.5(7) . . . . ? C2A C1A C9A C10A -37.9(8) . . . . ? C8A C1A C9A C10A -156.0(6) . . . . ? C15A C1A C9A C10A 82.1(7) . . . . ? C14A C9A C10A C11A 0.8(10) . . . . ? C1A C9A C10A C11A -177.9(6) . . . . ? C9A C10A C11A C12A -1.0(12) . . . . ? C10A C11A C12A C13A 1.5(11) . . . . ? C11A C12A C13A C14A -1.8(11) . . . . ? C12A C13A C14A C9A 1.7(10) . . . . ? C10A C9A C14A C13A -1.1(10) . . . . ? C1A C9A C14A C13A 177.5(6) . . . . ? C9A C1A C15A C22A -59.2(6) . . . . ? C2A C1A C15A C22A 62.3(6) . . . . ? C8A C1A C15A C22A 179.2(6) . . . . ? C9A C1A C15A C23A 178.9(5) . . . . ? C2A C1A C15A C23A -59.6(6) . . . . ? C8A C1A C15A C23A 57.2(6) . . . . ? C9A C1A C15A C16A 59.0(6) . . . . ? C2A C1A C15A C16A -179.5(6) . . . . ? C8A C1A C15A C16A -62.6(6) . . . . ? C22A C15A C16A C17A -50.7(7) . . . . ? C23A C15A C16A C17A 71.0(7) . . . . ? C1A C15A C16A C17A -170.3(5) . . . . ? C15A C16A C17A F12A 77.7(7) . . . . ? C15A C16A C17A F13A -42.9(7) . . . . ? C15A C16A C17A C18A -161.4(5) . . . . ? F12A C17A C18A F15A 79.5(6) . . . . ? F13A C17A C18A F15A -167.3(5) . . . . ? C16A C17A C18A F15A -44.1(7) . . . . ? F12A C17A C18A F14A -166.5(5) . . . . ? F13A C17A C18A F14A -53.2(6) . . . . ? C16A C17A C18A F14A 69.9(6) . . . . ? F12A C17A C18A C19A -43.6(7) . . . . ? F13A C17A C18A C19A 69.6(7) . . . . ? C16A C17A C18A C19A -167.2(6) . . . . ? F15A C18A C19A F16A -150.0(5) . . . . ? F14A C18A C19A F16A 94.5(6) . . . . ? C17A C18A C19A F16A -26.4(8) . . . . ? F15A C18A C19A C21A 90.5(6) . . . . ? F14A C18A C19A C21A -25.0(7) . . . . ? C17A C18A C19A C21A -146.0(6) . . . . ? F15A C18A C19A C20A -32.3(7) . . . . ? F14A C18A C19A C20A -147.8(6) . . . . ? C17A C18A C19A C20A 91.2(7) . . . . ? F16A C19A C20A F21A 82.1(7) . . . . ? C21A C19A C20A F21A -162.3(6) . . . . ? C18A C19A C20A F21A -38.2(8) . . . . ? F16A C19A C20A F20A -38.5(7) . . . . ? C21A C19A C20A F20A 77.0(7) . . . . ? C18A C19A C20A F20A -158.9(6) . . . . ? F16A C19A C20A F22A -158.2(5) . . . . ? C21A C19A C20A F22A -42.7(7) . . . . ? C18A C19A C20A F22A 81.4(7) . . . . ? F16A C19A C21A F19A -167.3(5) . . . . ? C18A C19A C21A F19A -46.4(8) . . . . ? C20A C19A C21A F19A 78.6(7) . . . . ? F16A C19A C21A F18A 70.1(7) . . . . ? C18A C19A C21A F18A -169.0(6) . . . . ? C20A C19A C21A F18A -44.0(8) . . . . ? F16A C19A C21A F17A -47.0(7) . . . . ? C18A C19A C21A F17A 73.9(7) . . . . ? C20A C19A C21A F17A -161.1(6) . . . . ? C22A C15A C23A C28A -24.6(8) . . . . ? C16A C15A C23A C28A -145.3(6) . . . . ? C1A C15A C23A C28A 97.4(6) . . . . ? C22A C15A C23A C24A 155.3(6) . . . . ? C16A C15A C23A C24A 34.6(8) . . . . ? C1A C15A C23A C24A -82.7(7) . . . . ? C28A C23A C24A C25A -1.2(10) . . . . ? C15A C23A C24A C25A 178.8(6) . . . . ? C23A C24A C25A C26A -0.4(11) . . . . ? C24A C25A C26A C27A 1.2(11) . . . . ? C25A C26A C27A C28A -0.3(10) . . . . ? C24A C23A C28A C27A 2.2(9) . . . . ? C15A C23A C28A C27A -177.9(5) . . . . ? C26A C27A C28A C23A -1.5(10) . . . . ? C9B C1B C2B C3B 68.9(8) . . . . ? C8B C1B C2B C3B -51.8(8) . . . . ? C15B C1B C2B C3B -170.4(5) . . . . ? C1B C2B C3B F1B -36.5(9) . . . . ? C1B C2B C3B F2B 81.0(7) . . . . ? C1B C2B C3B C4B -158.9(6) . . . . ? F1B C3B C4B F4B 178.1(5) . . . . ? F2B C3B C4B F4B 66.4(6) . . . . ? C2B C3B C4B F4B -55.1(7) . . . . ? F1B C3B C4B F3B -67.7(6) . . . . ? F2B C3B C4B F3B -179.4(5) . . . . ? C2B C3B C4B F3B 59.1(7) . . . . ? F1B C3B C4B C5B 52.1(7) . . . . ? F2B C3B C4B C5B -59.5(7) . . . . ? C2B C3B C4B C5B 178.9(6) . . . . ? F4B C4B C5B F5B 158.8(5) . . . . ? F3B C4B C5B F5B 45.3(6) . . . . ? C3B C4B C5B F5B -74.9(7) . . . . ? F4B C4B C5B C7B -83.2(7) . . . . ? F3B C4B C5B C7B 163.2(5) . . . . ? C3B C4B C5B C7B 43.0(8) . . . . ? F4B C4B C5B C6B 45.8(7) . . . . ? F3B C4B C5B C6B -67.7(7) . . . . ? C3B C4B C5B C6B 172.1(6) . . . . ? F5B C5B C6B F7B -79.3(7) . . . . ? C7B C5B C6B F7B 167.5(6) . . . . ? C4B C5B C6B F7B 35.6(8) . . . . ? F5B C5B C6B F6B 43.6(7) . . . . ? C7B C5B C6B F6B -69.6(8) . . . . ? C4B C5B C6B F6B 158.5(6) . . . . ? F5B C5B C6B F8B 160.9(5) . . . . ? C7B C5B C6B F8B 47.7(7) . . . . ? C4B C5B C6B F8B -84.1(7) . . . . ? F5B C5B C7B F9B -71.9(7) . . . . ? C4B C5B C7B F9B 169.6(5) . . . . ? C6B C5B C7B F9B 40.1(8) . . . . ? F5B C5B C7B F11B 47.0(7) . . . . ? C4B C5B C7B F11B -71.6(7) . . . . ? C6B C5B C7B F11B 158.9(5) . . . . ? F5B C5B C7B F10B 168.5(5) . . . . ? C4B C5B C7B F10B 50.0(8) . . . . ? C6B C5B C7B F10B -79.5(7) . . . . ? C2B C1B C9B C14B -149.4(6) . . . . ? C8B C1B C9B C14B -31.3(8) . . . . ? C15B C1B C9B C14B 92.3(7) . . . . ? C2B C1B C9B C10B 32.7(9) . . . . ? C8B C1B C9B C10B 150.8(6) . . . . ? C15B C1B C9B C10B -85.5(7) . . . . ? C14B C9B C10B C11B -1.1(11) . . . . ? C1B C9B C10B C11B 176.8(7) . . . . ? C9B C10B C11B C12B 0.7(12) . . . . ? C10B C11B C12B C13B -0.4(12) . . . . ? C11B C12B C13B C14B 0.6(11) . . . . ? C10B C9B C14B C13B 1.2(10) . . . . ? C1B C9B C14B C13B -176.8(6) . . . . ? C12B C13B C14B C9B -1.0(11) . . . . ? C9B C1B C15B C23B -179.8(6) . . . . ? C2B C1B C15B C23B 58.9(6) . . . . ? C8B C1B C15B C23B -56.4(7) . . . . ? C9B C1B C15B C16B -58.3(6) . . . . ? C2B C1B C15B C16B -179.7(6) . . . . ? C8B C1B C15B C16B 65.0(6) . . . . ? C9B C1B C15B C22B 58.3(6) . . . . ? C2B C1B C15B C22B -63.1(6) . . . . ? C8B C1B C15B C22B -178.4(6) . . . . ? C23B C15B C16B C17B -51.0(9) . . . . ? C22B C15B C16B C17B 71.1(8) . . . . ? C1B C15B C16B C17B -171.8(6) . . . . ? C15B C16B C17B F13B -25.5(10) . . . . ? C15B C16B C17B F12B 91.0(8) . . . . ? C15B C16B C17B C18B -156.1(6) . . . . ? F13B C17B C18B F15B -174.2(6) . . . . ? F12B C17B C18B F15B 73.9(7) . . . . ? C16B C17B C18B F15B -42.5(9) . . . . ? F13B C17B C18B F14B -58.9(8) . . . . ? F12B C17B C18B F14B -170.8(6) . . . . ? C16B C17B C18B F14B 72.8(8) . . . . ? F13B C17B C18B C19B 60.6(9) . . . . ? F12B C17B C18B C19B -51.3(9) . . . . ? C16B C17B C18B C19B -167.7(7) . . . . ? F15B C18B C19B F16B -50.8(7) . . . . ? F14B C18B C19B F16B -165.1(5) . . . . ? C17B C18B C19B F16B 75.5(8) . . . . ? F15B C18B C19B C20B -168.6(7) . . . . ? F14B C18B C19B C20B 77.1(8) . . . . ? C17B C18B C19B C20B -42.2(10) . . . . ? F15B C18B C19B C21B 61.9(8) . . . . ? F14B C18B C19B C21B -52.4(8) . . . . ? C17B C18B C19B C21B -171.8(7) . . . . ? F16B C19B C20B F22B -163.5(6) . . . . ? C21B C19B C20B F22B 82.0(8) . . . . ? C18B C19B C20B F22B -47.4(9) . . . . ? F16B C19B C20B F20B -43.2(8) . . . . ? C21B C19B C20B F20B -157.7(7) . . . . ? C18B C19B C20B F20B 72.9(10) . . . . ? F16B C19B C20B F21B 75.6(8) . . . . ? C21B C19B C20B F21B -39.0(11) . . . . ? C18B C19B C20B F21B -168.3(7) . . . . ? F16B C19B C21B F19B 76.1(8) . . . . ? C20B C19B C21B F19B -168.0(7) . . . . ? C18B C19B C21B F19B -36.0(9) . . . . ? F16B C19B C21B F18B -44.0(8) . . . . ? C20B C19B C21B F18B 71.8(9) . . . . ? C18B C19B C21B F18B -156.2(7) . . . . ? F16B C19B C21B F17B -162.2(6) . . . . ? C20B C19B C21B F17B -46.3(9) . . . . ? C18B C19B C21B F17B 85.7(8) . . . . ? C16B C15B C23B C24B -39.6(9) . . . . ? C22B C15B C23B C24B -160.3(6) . . . . ? C1B C15B C23B C24B 78.7(7) . . . . ? C16B C15B C23B C28B 139.6(6) . . . . ? C22B C15B C23B C28B 18.9(8) . . . . ? C1B C15B C23B C28B -102.0(7) . . . . ? C28B C23B C24B C25B 1.3(10) . . . . ? C15B C23B C24B C25B -179.4(6) . . . . ? C23B C24B C25B C26B 0.5(11) . . . . ? C24B C25B C26B C27B -1.4(11) . . . . ? C25B C26B C27B C28B 0.4(11) . . . . ? C26B C27B C28B C23B 1.5(10) . . . . ? C24B C23B C28B C27B -2.3(10) . . . . ? C15B C23B C28B C27B 178.4(6) . . . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.952 _refine_diff_density_min -0.358 _refine_diff_density_rms 0.116 # Attachment '- cif_4.txt' data_bud4 _database_code_depnum_ccdc_archive 'CCDC 832894' #TrackingRef '- cif_4.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C26 H16 F24 N2' _chemical_formula_sum 'C26 H16 F24 N2' _chemical_formula_weight 812.41 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 P2(1)/n _symmetry_space_group_name_Hall '-P 2yn ' 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 16.091(1) _cell_length_b 5.905(1) _cell_length_c 16.645(1) _cell_angle_alpha 90.00 _cell_angle_beta 110.047(5) _cell_angle_gamma 90.00 _cell_volume 1485.7(3) _cell_formula_units_Z 2 _cell_measurement_temperature 198(2) _cell_measurement_reflns_used 26400 _cell_measurement_theta_min 3.04 _cell_measurement_theta_max 25.40 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.53 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.816 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 804 _exptl_absorpt_coefficient_mu 0.213 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8954 _exptl_absorpt_correction_T_max 0.9769 _exptl_absorpt_process_details 'SADABS version 2.10 (Sheldrick,Bruker AXS Inc.,2002)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 198(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 KappaCCD _diffrn_measurement_method \f _diffrn_detector_area_resol_mean 9 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 24975 _diffrn_reflns_av_R_equivalents 0.0392 _diffrn_reflns_av_sigmaI/netI 0.0192 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 3.04 _diffrn_reflns_theta_max 25.40 _reflns_number_total 2732 _reflns_number_gt 2070 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius BV, 1999)' _computing_cell_refinement 'Dirax/lsq (Duisenberg, 1992)' _computing_data_reduction 'EvalCCD (Duisenberg et al., 2003)' _computing_structure_solution 'SIR2004 (Burla et al., 2005)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997), WinGX (Farrugia 1999), PLATON (Spek 2005)' _computing_molecular_graphics 'ORTEP-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX (Farrugia 1999), enCIFer (Allen et al. 2004)' _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^)+(0.0488P)^2^+1.0517P] 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 2732 _refine_ls_number_parameters 257 _refine_ls_number_restraints 7 _refine_ls_R_factor_all 0.0571 _refine_ls_R_factor_gt 0.0390 _refine_ls_wR_factor_ref 0.1058 _refine_ls_wR_factor_gt 0.0966 _refine_ls_goodness_of_fit_ref 1.017 _refine_ls_restrained_S_all 1.016 _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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.55118(12) -0.0171(4) 0.01648(13) 0.0285(5) Uani 1 1 d . . . H1A H 0.5794 0.1237 0.0043 0.034 Uiso 1 1 calc R . . C2 C 0.57545(13) -0.2167(4) -0.03124(13) 0.0312(5) Uani 1 1 d . . . H2A H 0.5676 -0.3606 -0.0042 0.037 Uiso 1 1 calc R . . H2B H 0.5345 -0.2182 -0.0912 0.037 Uiso 1 1 calc R . . C3 C 0.66862(13) -0.2030(4) -0.03062(13) 0.0314(5) Uani 1 1 d . . . C4 C 0.70019(13) -0.4133(4) -0.06613(12) 0.0289(5) Uani 1 1 d . . . C5 C 0.78844(13) -0.3932(4) -0.08373(13) 0.0306(5) Uani 1 1 d . . . C6 C 0.82774(13) -0.6167(4) -0.10222(13) 0.0305(5) Uani 1 1 d . A . C7 C 0.90444(13) -0.5953(4) -0.13743(13) 0.0337(5) Uani 1 1 d D . . C8A C 0.9607(5) -0.8079(13) -0.1275(6) 0.0438(19) Uani 0.530(5) 1 d PD A 1 H8A H 0.9874 -0.8512 -0.0659 0.053 Uiso 0.530(5) 1 calc PR A 1 F25A F 0.9091(2) -0.9750(5) -0.1726(2) 0.0603(11) Uani 0.530(5) 1 d PD A 1 F26A F 1.0243(5) -0.7701(19) -0.1613(4) 0.0543(15) Uani 0.530(5) 1 d PD A 1 C8B C 0.9403(7) -0.8282(16) -0.1531(6) 0.0438(19) Uani 0.470(5) 1 d PD A 2 H8B H 0.8912 -0.9277 -0.1888 0.053 Uiso 0.470(5) 1 calc PR A 2 F25B F 0.9827(2) -0.9234(6) -0.0761(2) 0.0584(12) Uani 0.470(5) 1 d PD A 2 F26B F 0.9993(6) -0.789(2) -0.1925(5) 0.068(2) Uani 0.470(5) 1 d PD A 2 C9 C 0.58535(13) -0.0580(4) 0.11225(13) 0.0323(5) Uani 1 1 d . . . N10 N 0.55930(13) -0.2518(4) 0.13778(13) 0.0458(5) Uani 1 1 d . . . C11 C 0.5862(2) -0.2888(6) 0.22265(18) 0.0627(8) Uani 1 1 d . . . H11A H 0.5684 -0.4255 0.2421 0.075 Uiso 1 1 calc R . . C12 C 0.6379(2) -0.1415(7) 0.28283(17) 0.0673(9) Uani 1 1 d . . . H12A H 0.6548 -0.1754 0.3421 0.081 Uiso 1 1 calc R . . C13 C 0.66456(18) 0.0554(6) 0.25566(16) 0.0596(8) Uani 1 1 d . . . H13A H 0.7007 0.1607 0.2957 0.071 Uiso 1 1 calc R . . C14 C 0.63800(15) 0.0981(4) 0.16903(15) 0.0438(6) Uani 1 1 d . . . H14A H 0.6557 0.2335 0.1486 0.053 Uiso 1 1 calc R . . F15 F 0.72697(8) -0.1622(3) 0.04804(9) 0.0582(5) Uani 1 1 d . . . F16 F 0.67641(11) -0.0250(2) -0.07949(11) 0.0600(5) Uani 1 1 d . . . F17 F 0.63699(8) -0.4774(3) -0.13850(9) 0.0509(4) Uani 1 1 d . . . F18 F 0.70955(9) -0.5821(2) -0.00841(9) 0.0503(4) Uani 1 1 d . . . F19 F 0.77403(10) -0.2587(2) -0.15255(9) 0.0524(4) Uani 1 1 d . . . F20 F 0.84836(8) -0.2922(2) -0.01684(9) 0.0495(4) Uani 1 1 d . . . F21 F 0.85928(9) -0.7345(2) -0.02782(8) 0.0461(4) Uani 1 1 d . . . F22 F 0.76384(8) -0.7399(2) -0.15806(8) 0.0414(3) Uani 1 1 d . . . F23 F 0.87218(9) -0.5150(3) -0.21810(8) 0.0498(4) Uani 1 1 d . A . F24 F 0.96424(8) -0.4471(2) -0.09052(9) 0.0473(4) Uani 1 1 d . A . 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 0.0258(10) 0.0284(11) 0.0338(11) -0.0030(9) 0.0136(8) -0.0031(8) C2 0.0256(10) 0.0329(12) 0.0372(11) -0.0078(9) 0.0135(9) -0.0024(9) C3 0.0309(10) 0.0324(12) 0.0325(11) -0.0051(9) 0.0131(9) -0.0048(9) C4 0.0286(10) 0.0308(11) 0.0281(10) -0.0018(9) 0.0106(8) -0.0029(9) C5 0.0280(10) 0.0312(12) 0.0328(11) -0.0026(9) 0.0107(9) -0.0026(9) C6 0.0287(10) 0.0310(12) 0.0314(10) -0.0012(9) 0.0098(9) -0.0023(9) C7 0.0306(10) 0.0386(13) 0.0342(11) -0.0040(10) 0.0138(9) -0.0017(9) C8A 0.042(4) 0.044(2) 0.053(5) -0.007(3) 0.026(4) 0.000(3) F25A 0.0587(19) 0.0416(19) 0.091(2) -0.0169(16) 0.0385(17) -0.0043(15) F26A 0.045(3) 0.064(3) 0.069(4) -0.011(3) 0.038(3) 0.003(3) C8B 0.042(4) 0.044(2) 0.053(5) -0.007(3) 0.026(4) 0.000(3) F25B 0.055(2) 0.050(2) 0.070(2) 0.0115(18) 0.0207(17) 0.0235(16) F26B 0.062(5) 0.070(3) 0.093(6) -0.015(5) 0.054(4) 0.005(4) C9 0.0277(10) 0.0376(13) 0.0356(11) -0.0036(10) 0.0161(9) 0.0038(9) N10 0.0513(12) 0.0470(12) 0.0451(11) 0.0081(10) 0.0243(10) 0.0006(10) C11 0.0719(18) 0.072(2) 0.0542(16) 0.0229(16) 0.0342(15) 0.0144(16) C12 0.0626(18) 0.106(3) 0.0358(14) 0.0099(17) 0.0199(13) 0.0300(18) C13 0.0484(15) 0.087(2) 0.0378(14) -0.0143(15) 0.0071(12) 0.0096(15) C14 0.0379(12) 0.0501(15) 0.0424(13) -0.0106(12) 0.0126(10) 0.0017(11) F15 0.0307(7) 0.0903(12) 0.0494(8) -0.0378(8) 0.0083(6) 0.0003(7) F16 0.0781(11) 0.0334(8) 0.0968(12) 0.0129(8) 0.0663(10) 0.0071(7) F17 0.0272(6) 0.0711(10) 0.0507(8) -0.0328(7) 0.0088(6) -0.0037(6) F18 0.0597(9) 0.0380(8) 0.0703(10) 0.0156(7) 0.0445(8) 0.0085(7) F19 0.0636(9) 0.0456(8) 0.0651(9) 0.0238(7) 0.0440(8) 0.0184(7) F20 0.0278(6) 0.0558(9) 0.0646(9) -0.0328(7) 0.0154(6) -0.0097(6) F21 0.0506(8) 0.0492(8) 0.0456(7) 0.0180(6) 0.0255(6) 0.0161(7) F22 0.0346(6) 0.0418(8) 0.0517(8) -0.0182(6) 0.0200(6) -0.0114(6) F23 0.0482(8) 0.0701(10) 0.0362(7) 0.0097(7) 0.0211(6) 0.0045(7) F24 0.0332(7) 0.0587(9) 0.0537(8) -0.0158(7) 0.0196(6) -0.0137(6) _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 C9 1.517(3) . ? C1 C2 1.545(3) . ? C1 C1 1.560(4) 3_655 ? C1 H1A 1.0000 . ? C2 C3 1.498(3) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 F15 1.346(2) . ? C3 F16 1.361(3) . ? C3 C4 1.535(3) . ? C4 F17 1.337(2) . ? C4 F18 1.356(2) . ? C4 C5 1.550(3) . ? C5 F20 1.338(2) . ? C5 F19 1.347(2) . ? C5 C6 1.539(3) . ? C6 F22 1.340(2) . ? C6 F21 1.358(2) . ? C6 C7 1.542(3) . ? C7 F24 1.337(2) . ? C7 F23 1.349(3) . ? C7 C8A 1.523(8) . ? C7 C8B 1.548(10) . ? C8A F26A 1.345(6) . ? C8A F25A 1.342(7) . ? C8A H8A 1.0000 . ? C8B F26B 1.347(6) . ? C8B F25B 1.351(7) . ? C8B H8B 1.0000 . ? C9 N10 1.337(3) . ? C9 C14 1.383(3) . ? N10 C11 1.346(3) . ? C11 C12 1.371(4) . ? C11 H11A 0.9500 . ? C12 C13 1.369(5) . ? C12 H12A 0.9500 . ? C13 C14 1.379(4) . ? C13 H13A 0.9500 . ? C14 H14A 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 C9 C1 C2 110.77(17) . . ? C9 C1 C1 110.42(19) . 3_655 ? C2 C1 C1 109.9(2) . 3_655 ? C9 C1 H1A 108.6 . . ? C2 C1 H1A 108.6 . . ? C1 C1 H1A 108.6 3_655 . ? C3 C2 C1 112.58(17) . . ? C3 C2 H2A 109.1 . . ? C1 C2 H2A 109.1 . . ? C3 C2 H2B 109.1 . . ? C1 C2 H2B 109.1 . . ? H2A C2 H2B 107.8 . . ? F15 C3 F16 105.48(18) . . ? F15 C3 C2 112.29(17) . . ? F16 C3 C2 109.56(18) . . ? F15 C3 C4 107.87(17) . . ? F16 C3 C4 106.51(16) . . ? C2 C3 C4 114.59(17) . . ? F17 C4 F18 107.20(17) . . ? F17 C4 C3 109.01(16) . . ? F18 C4 C3 107.03(16) . . ? F17 C4 C5 108.33(16) . . ? F18 C4 C5 107.68(16) . . ? C3 C4 C5 117.15(17) . . ? F20 C5 F19 108.03(18) . . ? F20 C5 C6 108.70(16) . . ? F19 C5 C6 107.36(16) . . ? F20 C5 C4 108.82(16) . . ? F19 C5 C4 107.71(16) . . ? C6 C5 C4 115.97(17) . . ? F22 C6 F21 108.21(17) . . ? F22 C6 C5 109.51(16) . . ? F21 C6 C5 107.91(16) . . ? F22 C6 C7 107.75(16) . . ? F21 C6 C7 106.91(16) . . ? C5 C6 C7 116.28(18) . . ? F24 C7 F23 107.80(18) . . ? F24 C7 C8A 101.2(3) . . ? F23 C7 C8A 114.2(4) . . ? F24 C7 C8B 116.4(4) . . ? F23 C7 C8B 100.5(3) . . ? C8A C7 C8B 17.1(6) . . ? F24 C7 C6 109.96(17) . . ? F23 C7 C6 108.78(17) . . ? C8A C7 C6 114.5(4) . . ? C8B C7 C6 112.6(4) . . ? F26A C8A F25A 107.6(7) . . ? F26A C8A C7 109.1(7) . . ? F25A C8A C7 108.3(6) . . ? F26A C8A H8A 110.6 . . ? F25A C8A H8A 110.6 . . ? C7 C8A H8A 110.6 . . ? F26B C8B F25B 108.9(9) . . ? F26B C8B C7 107.1(8) . . ? F25B C8B C7 107.8(6) . . ? F26B C8B H8B 111.0 . . ? F25B C8B H8B 111.0 . . ? C7 C8B H8B 111.0 . . ? N10 C9 C14 122.6(2) . . ? N10 C9 C1 115.46(19) . . ? C14 C9 C1 121.9(2) . . ? C9 N10 C11 116.7(2) . . ? N10 C11 C12 124.1(3) . . ? N10 C11 H11A 118.0 . . ? C12 C11 H11A 118.0 . . ? C13 C12 C11 118.5(3) . . ? C13 C12 H12A 120.7 . . ? C11 C12 H12A 120.7 . . ? C12 C13 C14 118.7(3) . . ? C12 C13 H13A 120.6 . . ? C14 C13 H13A 120.6 . . ? C13 C14 C9 119.4(3) . . ? C13 C14 H14A 120.3 . . ? C9 C14 H14A 120.3 . . ? 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 C9 C1 C2 C3 -80.9(2) . . . . ? C1 C1 C2 C3 156.8(2) 3_655 . . . ? C1 C2 C3 F15 48.4(2) . . . . ? C1 C2 C3 F16 -68.5(2) . . . . ? C1 C2 C3 C4 171.89(17) . . . . ? F15 C3 C4 F17 170.91(16) . . . . ? F16 C3 C4 F17 -76.3(2) . . . . ? C2 C3 C4 F17 45.1(2) . . . . ? F15 C3 C4 F18 55.3(2) . . . . ? F16 C3 C4 F18 168.10(16) . . . . ? C2 C3 C4 F18 -70.6(2) . . . . ? F15 C3 C4 C5 -65.7(2) . . . . ? F16 C3 C4 C5 47.2(2) . . . . ? C2 C3 C4 C5 168.46(17) . . . . ? F17 C4 C5 F20 169.34(17) . . . . ? F18 C4 C5 F20 -75.0(2) . . . . ? C3 C4 C5 F20 45.6(2) . . . . ? F17 C4 C5 F19 52.5(2) . . . . ? F18 C4 C5 F19 168.10(16) . . . . ? C3 C4 C5 F19 -71.3(2) . . . . ? F17 C4 C5 C6 -67.8(2) . . . . ? F18 C4 C5 C6 47.8(2) . . . . ? C3 C4 C5 C6 168.45(17) . . . . ? F20 C5 C6 F22 168.63(16) . . . . ? F19 C5 C6 F22 -74.7(2) . . . . ? C4 C5 C6 F22 45.7(2) . . . . ? F20 C5 C6 F21 51.1(2) . . . . ? F19 C5 C6 F21 167.68(15) . . . . ? C4 C5 C6 F21 -71.9(2) . . . . ? F20 C5 C6 C7 -69.0(2) . . . . ? F19 C5 C6 C7 47.6(2) . . . . ? C4 C5 C6 C7 168.09(17) . . . . ? F22 C6 C7 F24 171.06(17) . . . . ? F21 C6 C7 F24 -72.8(2) . . . . ? C5 C6 C7 F24 47.8(2) . . . . ? F22 C6 C7 F23 53.2(2) . . . . ? F21 C6 C7 F23 169.34(17) . . . . ? C5 C6 C7 F23 -70.1(2) . . . . ? F22 C6 C7 C8A -75.8(4) . . . . ? F21 C6 C7 C8A 40.3(4) . . . . ? C5 C6 C7 C8A 160.9(4) . . . . ? F22 C6 C7 C8B -57.3(4) . . . . ? F21 C6 C7 C8B 58.8(4) . . . . ? C5 C6 C7 C8B 179.4(4) . . . . ? F24 C7 C8A F26A -62.6(6) . . . . ? F23 C7 C8A F26A 52.9(6) . . . . ? C8B C7 C8A F26A 92(2) . . . . ? C6 C7 C8A F26A 179.2(4) . . . . ? F24 C7 C8A F25A -179.4(5) . . . . ? F23 C7 C8A F25A -63.9(6) . . . . ? C8B C7 C8A F25A -25.0(19) . . . . ? C6 C7 C8A F25A 62.4(7) . . . . ? F24 C7 C8B F26B -58.6(7) . . . . ? F23 C7 C8B F26B 57.5(7) . . . . ? C8A C7 C8B F26B -87(2) . . . . ? C6 C7 C8B F26B 173.1(5) . . . . ? F24 C7 C8B F25B 58.4(8) . . . . ? F23 C7 C8B F25B 174.5(6) . . . . ? C8A C7 C8B F25B 30.1(18) . . . . ? C6 C7 C8B F25B -69.9(8) . . . . ? C2 C1 C9 N10 -55.3(2) . . . . ? C1 C1 C9 N10 66.6(3) 3_655 . . . ? C2 C1 C9 C14 126.2(2) . . . . ? C1 C1 C9 C14 -111.8(2) 3_655 . . . ? C14 C9 N10 C11 0.6(3) . . . . ? C1 C9 N10 C11 -177.8(2) . . . . ? C9 N10 C11 C12 -0.1(4) . . . . ? N10 C11 C12 C13 -0.4(4) . . . . ? C11 C12 C13 C14 0.4(4) . . . . ? C12 C13 C14 C9 0.1(4) . . . . ? N10 C9 C14 C13 -0.6(3) . . . . ? C1 C9 C14 C13 177.7(2) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.40 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.392 _refine_diff_density_min -0.228 _refine_diff_density_rms 0.044