# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2009 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'Shu-Li You' _publ_contact_author_email SLYOU@MAIL.SIOC.AC.CN _publ_section_title ; Highly Enantioselective Intramolecular Michael Reactions by D-Camphor-Derived Triazolium Salts ; loop_ _publ_author_name 'Shu-Li You' 'Yi Li' 'Xue-Qiang Wang' # Attachment 'cd28459.cif' data_cd28459 _database_code_depnum_ccdc_archive 'CCDC 740388' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C19 H13 F3 O2' _chemical_formula_weight 330.29 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 8.9074(11) _cell_length_b 15.5638(19) _cell_length_c 24.123(3) _cell_angle_alpha 90.00 _cell_angle_beta 95.334(2) _cell_angle_gamma 90.00 _cell_volume 3329.7(7) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2233 _cell_measurement_theta_min 5.088 _cell_measurement_theta_max 41.183 _exptl_crystal_description prismatic _exptl_crystal_colour yellow _exptl_crystal_size_max 0.403 _exptl_crystal_size_mid 0.352 _exptl_crystal_size_min 0.278 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.318 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1360 _exptl_absorpt_coefficient_mu 0.107 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.7964 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 17167 _diffrn_reflns_av_R_equivalents 0.0551 _diffrn_reflns_av_sigmaI/netI 0.0633 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 1.56 _diffrn_reflns_theta_max 25.50 _reflns_number_total 6205 _reflns_number_gt 2884 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0966P)^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 6205 _refine_ls_number_parameters 433 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1676 _refine_ls_R_factor_gt 0.0815 _refine_ls_wR_factor_ref 0.2309 _refine_ls_wR_factor_gt 0.1924 _refine_ls_goodness_of_fit_ref 1.033 _refine_ls_restrained_S_all 1.033 _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 F1 F 0.3495(3) 0.5331(2) 0.47499(12) 0.1130(11) Uani 1 1 d . . . F2 F 0.4415(3) 0.6454(2) 0.44113(15) 0.1369(13) Uani 1 1 d . . . F3 F 0.4826(3) 0.5228(2) 0.40736(13) 0.1181(11) Uani 1 1 d . . . F4 F 0.1359(3) 0.6066(2) 0.03343(12) 0.1195(12) Uani 1 1 d . . . F5 F 0.0419(3) 0.5009(2) 0.07186(14) 0.1299(13) Uani 1 1 d . . . F6 F 0.0089(3) 0.6259(2) 0.10166(13) 0.1144(11) Uani 1 1 d . . . O1 O 0.0672(4) 0.63182(19) 0.28195(12) 0.0918(11) Uani 1 1 d . . . O2 O -0.2440(4) 0.3034(2) 0.40797(17) 0.1201(14) Uani 1 1 d . . . O3 O 0.4209(4) 0.51340(19) 0.22748(12) 0.0890(11) Uani 1 1 d . . . O4 O 0.7390(4) 0.8376(2) 0.08652(18) 0.1229(14) Uani 1 1 d . . . C1 C 0.3784(5) 0.5705(3) 0.4276(2) 0.0765(13) Uani 1 1 d . . . C2 C 0.2386(4) 0.5803(2) 0.38896(17) 0.0530(10) Uani 1 1 d . . . C3 C 0.2321(4) 0.5467(2) 0.33859(17) 0.0566(10) Uani 1 1 d . . . H3 H 0.3129 0.5136 0.3293 0.068 Uiso 1 1 calc R . . C4 C 0.1013(5) 0.5591(3) 0.29549(16) 0.0609(11) Uani 1 1 d . . . C5 C 0.0213(5) 0.4841(3) 0.27117(16) 0.0599(11) Uani 1 1 d . . . C6 C -0.1003(6) 0.4956(4) 0.23116(19) 0.0938(16) Uani 1 1 d . . . H6 H -0.1299 0.5506 0.2198 0.113 Uiso 1 1 calc R . . C7 C -0.1756(7) 0.4254(5) 0.2086(2) 0.119(2) Uani 1 1 d . . . H7 H -0.2579 0.4330 0.1824 0.142 Uiso 1 1 calc R . . C8 C -0.1311(8) 0.3437(4) 0.2243(3) 0.110(2) Uani 1 1 d . . . H8 H -0.1807 0.2967 0.2073 0.133 Uiso 1 1 calc R . . C9 C -0.0156(7) 0.3307(3) 0.2643(2) 0.1018(18) Uani 1 1 d . . . H9 H 0.0114 0.2754 0.2759 0.122 Uiso 1 1 calc R . . C10 C 0.0604(5) 0.4005(3) 0.28720(19) 0.0784(14) Uani 1 1 d . . . H10 H 0.1404 0.3918 0.3142 0.094 Uiso 1 1 calc R . . C11 C 0.1135(4) 0.6283(2) 0.41071(14) 0.0514(10) Uani 1 1 d . . . C12 C 0.1164(6) 0.7166(3) 0.41439(17) 0.0716(13) Uani 1 1 d . . . H12 H 0.1992 0.7465 0.4034 0.086 Uiso 1 1 calc R . . C13 C -0.0007(7) 0.7613(3) 0.4339(2) 0.0879(17) Uani 1 1 d . . . H13 H 0.0034 0.8209 0.4358 0.106 Uiso 1 1 calc R . . C14 C -0.1220(6) 0.7193(3) 0.45042(19) 0.0849(15) Uani 1 1 d . . . H14 H -0.2004 0.7500 0.4639 0.102 Uiso 1 1 calc R . . C15 C -0.1292(5) 0.6313(3) 0.44724(16) 0.0679(12) Uani 1 1 d . . . H15 H -0.2131 0.6028 0.4585 0.081 Uiso 1 1 calc R . . C16 C -0.0130(4) 0.5840(2) 0.42748(14) 0.0486(10) Uani 1 1 d . . . C17 C -0.0220(4) 0.4902(2) 0.42405(14) 0.0530(10) Uani 1 1 d . . . H17 H 0.0694 0.4609 0.4263 0.064 Uiso 1 1 calc R . . C18 C -0.1448(5) 0.4425(3) 0.41817(17) 0.0655(12) Uani 1 1 d . . . H18 H -0.2387 0.4690 0.4158 0.079 Uiso 1 1 calc R . . C19 C -0.1367(5) 0.3499(3) 0.41532(19) 0.0775(14) Uani 1 1 d . . . H19 H -0.0418 0.3246 0.4195 0.093 Uiso 1 1 calc R . . C20 C 0.1099(5) 0.5749(3) 0.0818(2) 0.0751(13) Uani 1 1 d . . . C21 C 0.2498(4) 0.5639(2) 0.11966(16) 0.0493(10) Uani 1 1 d . . . C22 C 0.2596(4) 0.5997(2) 0.17008(16) 0.0528(10) Uani 1 1 d . . . H22 H 0.1815 0.6351 0.1793 0.063 Uiso 1 1 calc R . . C23 C 0.3907(5) 0.5856(3) 0.21242(15) 0.0560(11) Uani 1 1 d . . . C24 C 0.4762(5) 0.6616(3) 0.23553(15) 0.0600(11) Uani 1 1 d . . . C25 C 0.5969(6) 0.6492(3) 0.27531(19) 0.0892(15) Uani 1 1 d . . . H25 H 0.6222 0.5942 0.2879 0.107 Uiso 1 1 calc R . . C26 C 0.6792(7) 0.7192(5) 0.2961(2) 0.117(2) Uani 1 1 d . . . H26 H 0.7604 0.7115 0.3228 0.140 Uiso 1 1 calc R . . C27 C 0.6409(8) 0.7993(5) 0.2774(3) 0.116(2) Uani 1 1 d . . . H27 H 0.6966 0.8464 0.2914 0.139 Uiso 1 1 calc R . . C28 C 0.5222(7) 0.8116(3) 0.2385(2) 0.0984(18) Uani 1 1 d . . . H28 H 0.4971 0.8669 0.2262 0.118 Uiso 1 1 calc R . . C29 C 0.4400(5) 0.7436(3) 0.21731(18) 0.0758(13) Uani 1 1 d . . . H29 H 0.3593 0.7524 0.1906 0.091 Uiso 1 1 calc R . . C30 C 0.3739(4) 0.5160(2) 0.09782(14) 0.0487(10) Uani 1 1 d . . . C31 C 0.3656(5) 0.4269(3) 0.09467(16) 0.0678(12) Uani 1 1 d . . . H31 H 0.2797 0.3994 0.1048 0.081 Uiso 1 1 calc R . . C32 C 0.4807(7) 0.3787(3) 0.07699(19) 0.0798(15) Uani 1 1 d . . . H32 H 0.4730 0.3191 0.0756 0.096 Uiso 1 1 calc R . . C33 C 0.6070(6) 0.4187(3) 0.06134(17) 0.0754(14) Uani 1 1 d . . . H33 H 0.6856 0.3863 0.0493 0.090 Uiso 1 1 calc R . . C34 C 0.6177(5) 0.5068(3) 0.06342(15) 0.0631(11) Uani 1 1 d . . . H34 H 0.7033 0.5336 0.0524 0.076 Uiso 1 1 calc R . . C35 C 0.5022(4) 0.5565(2) 0.08184(14) 0.0493(10) Uani 1 1 d . . . C36 C 0.5129(4) 0.6510(2) 0.08243(14) 0.0515(10) Uani 1 1 d . . . H36 H 0.4223 0.6807 0.0822 0.062 Uiso 1 1 calc R . . C37 C 0.6354(5) 0.6983(3) 0.08320(18) 0.0692(12) Uani 1 1 d . . . H37 H 0.7282 0.6710 0.0831 0.083 Uiso 1 1 calc R . . C38 C 0.6315(5) 0.7901(3) 0.08416(19) 0.0776(14) Uani 1 1 d . . . H38 H 0.5369 0.8157 0.0828 0.093 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 F1 0.076(2) 0.174(3) 0.084(2) 0.037(2) -0.0178(17) 0.0147(19) F2 0.086(2) 0.124(3) 0.188(3) -0.017(2) -0.056(2) -0.033(2) F3 0.0500(17) 0.172(3) 0.130(3) 0.002(2) -0.0038(18) 0.0267(19) F4 0.086(2) 0.189(3) 0.079(2) 0.039(2) -0.0178(17) 0.017(2) F5 0.092(2) 0.112(2) 0.174(3) -0.019(2) -0.052(2) -0.031(2) F6 0.0477(16) 0.154(3) 0.139(3) -0.018(2) -0.0083(17) 0.0277(18) O1 0.130(3) 0.062(2) 0.078(2) 0.0030(16) -0.021(2) 0.017(2) O2 0.082(3) 0.093(3) 0.186(4) -0.022(2) 0.016(3) -0.040(2) O3 0.131(3) 0.0563(19) 0.075(2) -0.0006(16) -0.018(2) 0.0107(19) O4 0.089(3) 0.098(3) 0.185(4) -0.017(2) 0.028(3) -0.047(2) C1 0.044(3) 0.091(4) 0.092(4) -0.003(3) -0.010(3) -0.005(3) C2 0.039(2) 0.052(2) 0.067(3) 0.011(2) 0.001(2) -0.0055(19) C3 0.050(3) 0.056(2) 0.065(3) 0.006(2) 0.012(2) 0.004(2) C4 0.072(3) 0.061(3) 0.050(3) 0.004(2) 0.010(2) 0.006(2) C5 0.062(3) 0.067(3) 0.051(2) -0.004(2) 0.006(2) -0.002(2) C6 0.105(4) 0.103(4) 0.068(3) -0.001(3) -0.021(3) 0.000(3) C7 0.121(5) 0.139(6) 0.087(4) -0.013(4) -0.034(4) -0.013(5) C8 0.115(5) 0.113(5) 0.102(5) -0.041(4) 0.003(4) -0.038(4) C9 0.112(5) 0.081(4) 0.115(5) -0.014(3) 0.020(4) -0.016(4) C10 0.073(3) 0.070(3) 0.091(3) -0.010(3) 0.003(3) 0.003(3) C11 0.053(3) 0.053(2) 0.046(2) -0.0001(18) -0.010(2) 0.001(2) C12 0.087(4) 0.046(3) 0.077(3) -0.008(2) -0.015(3) -0.010(3) C13 0.118(5) 0.051(3) 0.089(4) -0.018(3) -0.017(4) 0.006(3) C14 0.090(4) 0.082(4) 0.081(4) -0.015(3) 0.001(3) 0.034(3) C15 0.059(3) 0.071(3) 0.072(3) -0.005(2) 0.004(2) 0.014(2) C16 0.044(2) 0.053(2) 0.046(2) -0.0012(18) -0.0053(19) 0.008(2) C17 0.045(2) 0.060(3) 0.054(2) 0.0068(19) 0.008(2) 0.013(2) C18 0.036(2) 0.068(3) 0.092(3) -0.010(2) 0.002(2) -0.003(2) C19 0.058(3) 0.077(4) 0.098(4) 0.001(3) 0.011(3) -0.013(3) C20 0.043(3) 0.089(4) 0.090(4) 0.004(3) -0.007(3) 0.003(3) C21 0.046(2) 0.047(2) 0.055(2) 0.0020(19) 0.006(2) -0.0094(19) C22 0.047(2) 0.048(2) 0.065(3) 0.003(2) 0.013(2) 0.0047(19) C23 0.071(3) 0.054(3) 0.045(2) -0.003(2) 0.013(2) 0.011(2) C24 0.062(3) 0.075(3) 0.044(2) -0.012(2) 0.008(2) 0.000(2) C25 0.088(4) 0.104(4) 0.072(3) -0.008(3) -0.013(3) 0.001(3) C26 0.105(5) 0.154(6) 0.085(4) -0.026(4) -0.021(4) -0.028(5) C27 0.130(6) 0.127(6) 0.089(4) -0.040(4) 0.005(4) -0.047(5) C28 0.118(5) 0.064(3) 0.116(5) -0.026(3) 0.026(4) -0.021(3) C29 0.084(4) 0.059(3) 0.083(3) -0.012(3) 0.005(3) 0.000(3) C30 0.051(2) 0.050(2) 0.043(2) -0.0025(17) -0.0061(19) 0.000(2) C31 0.077(3) 0.060(3) 0.066(3) -0.004(2) 0.005(3) -0.004(3) C32 0.109(4) 0.057(3) 0.071(3) -0.003(2) -0.007(3) 0.021(3) C33 0.085(4) 0.075(3) 0.064(3) -0.005(2) -0.003(3) 0.031(3) C34 0.056(3) 0.076(3) 0.057(3) 0.002(2) 0.003(2) 0.016(2) C35 0.046(2) 0.058(3) 0.042(2) -0.0015(18) -0.0047(19) 0.009(2) C36 0.041(2) 0.059(3) 0.055(2) 0.0006(18) 0.0041(19) 0.001(2) C37 0.045(3) 0.074(3) 0.088(3) -0.017(2) 0.008(2) -0.008(2) C38 0.061(3) 0.067(3) 0.106(4) -0.003(3) 0.015(3) -0.015(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 F1 C1 1.329(5) . ? F2 C1 1.322(5) . ? F3 C1 1.318(5) . ? F4 C20 1.307(5) . ? F5 C20 1.313(5) . ? F6 C20 1.322(5) . ? O1 C4 1.209(4) . ? O2 C19 1.198(5) . ? O3 C23 1.204(4) . ? O4 C38 1.207(5) . ? C1 C2 1.493(5) . ? C2 C3 1.319(5) . ? C2 C11 1.478(5) . ? C3 C4 1.500(5) . ? C3 H3 0.9300 . ? C4 C5 1.462(5) . ? C5 C10 1.393(5) . ? C5 C6 1.393(6) . ? C6 C7 1.368(7) . ? C6 H6 0.9300 . ? C7 C8 1.375(7) . ? C7 H7 0.9300 . ? C8 C9 1.358(7) . ? C8 H8 0.9300 . ? C9 C10 1.368(6) . ? C9 H9 0.9300 . ? C10 H10 0.9300 . ? C11 C12 1.378(5) . ? C11 C16 1.411(5) . ? C12 C13 1.373(6) . ? C12 H12 0.9300 . ? C13 C14 1.355(7) . ? C13 H13 0.9300 . ? C14 C15 1.373(6) . ? C14 H14 0.9300 . ? C15 C16 1.389(5) . ? C15 H15 0.9300 . ? C16 C17 1.465(5) . ? C17 C18 1.319(5) . ? C17 H17 0.9300 . ? C18 C19 1.445(6) . ? C18 H18 0.9300 . ? C19 H19 0.9300 . ? C20 C21 1.485(5) . ? C21 C22 1.333(5) . ? C21 C30 1.471(5) . ? C22 C23 1.495(5) . ? C22 H22 0.9300 . ? C23 C24 1.487(5) . ? C24 C29 1.379(5) . ? C24 C25 1.386(6) . ? C25 C26 1.380(7) . ? C25 H25 0.9300 . ? C26 C27 1.360(7) . ? C26 H26 0.9300 . ? C27 C28 1.361(8) . ? C27 H27 0.9300 . ? C28 C29 1.359(6) . ? C28 H28 0.9300 . ? C29 H29 0.9300 . ? C30 C31 1.390(5) . ? C30 C35 1.391(5) . ? C31 C32 1.370(6) . ? C31 H31 0.9300 . ? C32 C33 1.369(6) . ? C32 H32 0.9300 . ? C33 C34 1.376(6) . ? C33 H33 0.9300 . ? C34 C35 1.392(5) . ? C34 H34 0.9300 . ? C35 C36 1.473(5) . ? C36 C37 1.315(5) . ? C36 H36 0.9300 . ? C37 C38 1.429(6) . ? C37 H37 0.9300 . ? C38 H38 0.9300 . ? 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 F3 C1 F2 106.9(4) . . ? F3 C1 F1 105.7(4) . . ? F2 C1 F1 106.7(4) . . ? F3 C1 C2 113.6(4) . . ? F2 C1 C2 112.0(4) . . ? F1 C1 C2 111.4(4) . . ? C3 C2 C11 123.8(4) . . ? C3 C2 C1 119.9(4) . . ? C11 C2 C1 116.3(4) . . ? C2 C3 C4 123.6(4) . . ? C2 C3 H3 118.2 . . ? C4 C3 H3 118.2 . . ? O1 C4 C5 122.6(4) . . ? O1 C4 C3 117.8(4) . . ? C5 C4 C3 119.6(4) . . ? C10 C5 C6 118.1(4) . . ? C10 C5 C4 122.3(4) . . ? C6 C5 C4 119.6(4) . . ? C7 C6 C5 119.6(5) . . ? C7 C6 H6 120.2 . . ? C5 C6 H6 120.2 . . ? C6 C7 C8 120.7(5) . . ? C6 C7 H7 119.6 . . ? C8 C7 H7 119.6 . . ? C9 C8 C7 120.9(5) . . ? C9 C8 H8 119.6 . . ? C7 C8 H8 119.6 . . ? C8 C9 C10 118.9(5) . . ? C8 C9 H9 120.6 . . ? C10 C9 H9 120.6 . . ? C9 C10 C5 121.8(5) . . ? C9 C10 H10 119.1 . . ? C5 C10 H10 119.1 . . ? C12 C11 C16 118.6(4) . . ? C12 C11 C2 121.1(4) . . ? C16 C11 C2 120.3(3) . . ? C13 C12 C11 121.1(5) . . ? C13 C12 H12 119.4 . . ? C11 C12 H12 119.4 . . ? C14 C13 C12 120.6(5) . . ? C14 C13 H13 119.7 . . ? C12 C13 H13 119.7 . . ? C13 C14 C15 120.0(5) . . ? C13 C14 H14 120.0 . . ? C15 C14 H14 120.0 . . ? C14 C15 C16 121.0(5) . . ? C14 C15 H15 119.5 . . ? C16 C15 H15 119.5 . . ? C15 C16 C11 118.7(4) . . ? C15 C16 C17 120.5(4) . . ? C11 C16 C17 120.8(3) . . ? C18 C17 C16 127.5(4) . . ? C18 C17 H17 116.3 . . ? C16 C17 H17 116.3 . . ? C17 C18 C19 121.5(4) . . ? C17 C18 H18 119.2 . . ? C19 C18 H18 119.2 . . ? O2 C19 C18 124.5(5) . . ? O2 C19 H19 117.8 . . ? C18 C19 H19 117.8 . . ? F4 C20 F5 106.5(4) . . ? F4 C20 F6 106.3(4) . . ? F5 C20 F6 105.9(4) . . ? F4 C20 C21 112.6(4) . . ? F5 C20 C21 110.9(4) . . ? F6 C20 C21 114.0(4) . . ? C22 C21 C30 123.4(4) . . ? C22 C21 C20 119.5(4) . . ? C30 C21 C20 117.0(4) . . ? C21 C22 C23 122.9(4) . . ? C21 C22 H22 118.6 . . ? C23 C22 H22 118.6 . . ? O3 C23 C24 122.5(4) . . ? O3 C23 C22 118.8(4) . . ? C24 C23 C22 118.6(3) . . ? C29 C24 C25 119.5(4) . . ? C29 C24 C23 121.4(4) . . ? C25 C24 C23 119.1(4) . . ? C26 C25 C24 119.6(5) . . ? C26 C25 H25 120.2 . . ? C24 C25 H25 120.2 . . ? C27 C26 C25 119.6(6) . . ? C27 C26 H26 120.2 . . ? C25 C26 H26 120.2 . . ? C26 C27 C28 120.9(6) . . ? C26 C27 H27 119.6 . . ? C28 C27 H27 119.6 . . ? C29 C28 C27 120.4(5) . . ? C29 C28 H28 119.8 . . ? C27 C28 H28 119.8 . . ? C28 C29 C24 120.0(5) . . ? C28 C29 H29 120.0 . . ? C24 C29 H29 120.0 . . ? C31 C30 C35 118.5(4) . . ? C31 C30 C21 119.2(4) . . ? C35 C30 C21 122.2(3) . . ? C32 C31 C30 121.7(5) . . ? C32 C31 H31 119.1 . . ? C30 C31 H31 119.1 . . ? C33 C32 C31 119.7(4) . . ? C33 C32 H32 120.2 . . ? C31 C32 H32 120.2 . . ? C32 C33 C34 119.9(5) . . ? C32 C33 H33 120.1 . . ? C34 C33 H33 120.1 . . ? C33 C34 C35 121.0(4) . . ? C33 C34 H34 119.5 . . ? C35 C34 H34 119.5 . . ? C30 C35 C34 119.1(4) . . ? C30 C35 C36 120.3(3) . . ? C34 C35 C36 120.6(4) . . ? C37 C36 C35 127.7(4) . . ? C37 C36 H36 116.1 . . ? C35 C36 H36 116.1 . . ? C36 C37 C38 122.6(4) . . ? C36 C37 H37 118.7 . . ? C38 C37 H37 118.7 . . ? O4 C38 C37 126.3(5) . . ? O4 C38 H38 116.8 . . ? C37 C38 H38 116.8 . . ? 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 F3 C1 C2 C3 -3.8(6) . . . . ? F2 C1 C2 C3 117.5(5) . . . . ? F1 C1 C2 C3 -123.1(4) . . . . ? F3 C1 C2 C11 176.0(4) . . . . ? F2 C1 C2 C11 -62.7(5) . . . . ? F1 C1 C2 C11 56.7(5) . . . . ? C11 C2 C3 C4 5.1(6) . . . . ? C1 C2 C3 C4 -175.1(4) . . . . ? C2 C3 C4 O1 57.9(6) . . . . ? C2 C3 C4 C5 -122.7(4) . . . . ? O1 C4 C5 C10 -179.6(4) . . . . ? C3 C4 C5 C10 1.1(6) . . . . ? O1 C4 C5 C6 -0.7(6) . . . . ? C3 C4 C5 C6 180.0(4) . . . . ? C10 C5 C6 C7 -0.7(7) . . . . ? C4 C5 C6 C7 -179.6(5) . . . . ? C5 C6 C7 C8 -1.2(9) . . . . ? C6 C7 C8 C9 2.9(10) . . . . ? C7 C8 C9 C10 -2.7(9) . . . . ? C8 C9 C10 C5 0.8(8) . . . . ? C6 C5 C10 C9 0.9(7) . . . . ? C4 C5 C10 C9 179.8(4) . . . . ? C3 C2 C11 C12 -103.5(5) . . . . ? C1 C2 C11 C12 76.7(5) . . . . ? C3 C2 C11 C16 75.6(5) . . . . ? C1 C2 C11 C16 -104.2(4) . . . . ? C16 C11 C12 C13 0.0(6) . . . . ? C2 C11 C12 C13 179.2(4) . . . . ? C11 C12 C13 C14 0.4(7) . . . . ? C12 C13 C14 C15 -0.6(7) . . . . ? C13 C14 C15 C16 0.3(7) . . . . ? C14 C15 C16 C11 0.1(6) . . . . ? C14 C15 C16 C17 -179.8(4) . . . . ? C12 C11 C16 C15 -0.3(5) . . . . ? C2 C11 C16 C15 -179.4(3) . . . . ? C12 C11 C16 C17 179.6(3) . . . . ? C2 C11 C16 C17 0.5(5) . . . . ? C15 C16 C17 C18 26.6(6) . . . . ? C11 C16 C17 C18 -153.2(4) . . . . ? C16 C17 C18 C19 179.9(4) . . . . ? C17 C18 C19 O2 -177.1(5) . . . . ? F4 C20 C21 C22 125.4(4) . . . . ? F5 C20 C21 C22 -115.3(5) . . . . ? F6 C20 C21 C22 4.2(6) . . . . ? F4 C20 C21 C30 -52.2(5) . . . . ? F5 C20 C21 C30 67.1(5) . . . . ? F6 C20 C21 C30 -173.4(4) . . . . ? C30 C21 C22 C23 -8.0(6) . . . . ? C20 C21 C22 C23 174.6(4) . . . . ? C21 C22 C23 O3 -58.6(5) . . . . ? C21 C22 C23 C24 123.1(4) . . . . ? O3 C23 C24 C29 179.6(4) . . . . ? C22 C23 C24 C29 -2.2(6) . . . . ? O3 C23 C24 C25 1.0(6) . . . . ? C22 C23 C24 C25 179.2(4) . . . . ? C29 C24 C25 C26 -0.1(7) . . . . ? C23 C24 C25 C26 178.5(4) . . . . ? C24 C25 C26 C27 0.1(9) . . . . ? C25 C26 C27 C28 0.1(10) . . . . ? C26 C27 C28 C29 -0.3(9) . . . . ? C27 C28 C29 C24 0.4(8) . . . . ? C25 C24 C29 C28 -0.1(7) . . . . ? C23 C24 C29 C28 -178.7(4) . . . . ? C22 C21 C30 C31 105.7(4) . . . . ? C20 C21 C30 C31 -76.8(5) . . . . ? C22 C21 C30 C35 -72.1(5) . . . . ? C20 C21 C30 C35 105.3(4) . . . . ? C35 C30 C31 C32 0.8(6) . . . . ? C21 C30 C31 C32 -177.1(4) . . . . ? C30 C31 C32 C33 -0.7(7) . . . . ? C31 C32 C33 C34 -0.1(7) . . . . ? C32 C33 C34 C35 0.7(6) . . . . ? C31 C30 C35 C34 -0.2(5) . . . . ? C21 C30 C35 C34 177.7(3) . . . . ? C31 C30 C35 C36 177.6(3) . . . . ? C21 C30 C35 C36 -4.6(5) . . . . ? C33 C34 C35 C30 -0.6(5) . . . . ? C33 C34 C35 C36 -178.3(3) . . . . ? C30 C35 C36 C37 160.4(4) . . . . ? C34 C35 C36 C37 -21.9(6) . . . . ? C35 C36 C37 C38 -179.5(4) . . . . ? C36 C37 C38 O4 177.7(5) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.211 _refine_diff_density_min -0.200 _refine_diff_density_rms 0.044