# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is (c) The Royal Society of Chemistry 2009 data_global _journal_coden_Cambridge 177 _journal_volume ? _journal_page_first ? _journal_year ? loop_ _publ_author_name 'Jorge Salvador' _publ_contact_author_name 'ProfD JORGE SALVADOR ' _publ_contact_author_email SALVADOR@CI.UC.PT _publ_section_title ; Bismuth(III) salt-catalyzed Wagner-Meerwein rearrangement in terpenes. Application to the synthesis of the 18?-oleanane core and A-neo-18?-oleanene compounds from lupanes. ; # Attachment 'salvador2008.cif' data_rsrx55 _database_code_depnum_ccdc_archive 'CCDC 699289' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 19\b,28-epoxy-18\a-olean-3\b-yl acetate ; _chemical_name_common ? _chemical_melting_point 559 _chemical_formula_moiety 'C32 H52 O3' _chemical_formula_sum 'C32 H52 O3' _chemical_formula_weight 484.76 _chemical_absolute_configuration syn 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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M C2 _symmetry_space_group_name_Hall 'C 2y' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z' _cell_length_a 13.3520(2) _cell_length_b 6.54000(10) _cell_length_c 32.4439(5) _cell_angle_alpha 90.00 _cell_angle_beta 99.0080(10) _cell_angle_gamma 90.00 _cell_volume 2798.13(7) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 9681 _cell_measurement_theta_min 2.5425 _cell_measurement_theta_max 26.1742 _exptl_crystal_description tabular _exptl_crystal_colour colourless _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.151 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1072 _exptl_absorpt_coefficient_mu 0.071 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.934 _exptl_absorpt_correction_T_max 0.989 _exptl_absorpt_process_details '(SADABS; Sheldrick, 2000)' _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 'Bruker APEX CCD area-detector' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 26879 _diffrn_reflns_av_R_equivalents 0.0268 _diffrn_reflns_av_sigmaI/netI 0.0137 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -40 _diffrn_reflns_limit_l_max 40 _diffrn_reflns_theta_min 1.91 _diffrn_reflns_theta_max 26.24 _reflns_number_total 3074 _reflns_number_gt 2759 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'SMART (Bruker, 2003)' _computing_cell_refinement 'SAINT (Bruker, 2003)' _computing_data_reduction 'SAINT (Bruker, 2003)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement SHELXL-97 _computing_molecular_graphics 'PLATON (Spek, 2005)' _computing_publication_material SHELXL-97 _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^)+(0.0600P)^2^+0.5416P] 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 riding _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0014(5) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.5(14) _refine_ls_number_reflns 3074 _refine_ls_number_parameters 325 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0408 _refine_ls_R_factor_gt 0.0355 _refine_ls_wR_factor_ref 0.0994 _refine_ls_wR_factor_gt 0.0951 _refine_ls_goodness_of_fit_ref 1.036 _refine_ls_restrained_S_all 1.035 _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 0.22967(14) 0.6396(4) 0.33332(6) 0.0424(5) Uani 1 1 d . . . H1A H 0.1686 0.7171 0.3237 0.051 Uiso 1 1 calc R . . H1B H 0.2240 0.5092 0.3189 0.051 Uiso 1 1 calc R . . C2 C 0.23693(14) 0.6013(4) 0.38030(6) 0.0463(5) Uani 1 1 d . . . H2A H 0.2378 0.7309 0.3949 0.056 Uiso 1 1 calc R . . H2B H 0.1781 0.5248 0.3857 0.056 Uiso 1 1 calc R . . C3 C 0.33184(14) 0.4832(3) 0.39625(6) 0.0421(4) Uani 1 1 d . . . H3 H 0.3272 0.3493 0.3825 0.050 Uiso 1 1 calc R . . O3A O 0.33907(12) 0.4505(3) 0.44122(4) 0.0519(4) Uani 1 1 d . . . C3A C 0.30021(17) 0.2804(4) 0.45466(6) 0.0508(5) Uani 1 1 d . . . O3B O 0.25354(16) 0.1567(3) 0.43213(5) 0.0770(6) Uani 1 1 d . . . C3B C 0.3224(3) 0.2629(6) 0.50118(7) 0.0835(9) Uani 1 1 d . . . H3B1 H 0.2635 0.2124 0.5115 0.125 Uiso 1 1 calc R . . H3B2 H 0.3400 0.3950 0.5130 0.125 Uiso 1 1 calc R . . H3B3 H 0.3779 0.1702 0.5089 0.125 Uiso 1 1 calc R . . C4 C 0.43081(15) 0.5850(3) 0.38892(6) 0.0426(4) Uani 1 1 d . . . C23 C 0.45722(19) 0.7694(4) 0.41788(7) 0.0582(6) Uani 1 1 d . . . H23A H 0.3991 0.8571 0.4165 0.087 Uiso 1 1 calc R . . H23B H 0.5123 0.8440 0.4093 0.087 Uiso 1 1 calc R . . H23C H 0.4767 0.7225 0.4460 0.087 Uiso 1 1 calc R . . C24 C 0.51572(17) 0.4245(4) 0.39875(7) 0.0600(6) Uani 1 1 d . . . H24A H 0.5118 0.3620 0.4252 0.090 Uiso 1 1 calc R . . H24B H 0.5805 0.4899 0.3998 0.090 Uiso 1 1 calc R . . H24C H 0.5078 0.3217 0.3774 0.090 Uiso 1 1 calc R . . C5 C 0.41840(13) 0.6370(3) 0.34158(6) 0.0371(4) Uani 1 1 d . . . H5 H 0.4118 0.5037 0.3276 0.045 Uiso 1 1 calc R . . C6 C 0.51368(14) 0.7316(4) 0.32846(7) 0.0498(5) Uani 1 1 d . . . H6A H 0.5189 0.8739 0.3369 0.060 Uiso 1 1 calc R . . H6B H 0.5733 0.6606 0.3424 0.060 Uiso 1 1 calc R . . C7 C 0.50952(14) 0.7168(4) 0.28144(6) 0.0477(5) Uani 1 1 d . . . H7A H 0.5091 0.5737 0.2736 0.057 Uiso 1 1 calc R . . H7B H 0.5704 0.7781 0.2740 0.057 Uiso 1 1 calc R . . C8 C 0.41598(14) 0.8228(3) 0.25624(6) 0.0373(4) Uani 1 1 d . . . C26 C 0.4311(2) 1.0558(3) 0.26212(8) 0.0548(6) Uani 1 1 d . . . H26A H 0.4505 1.0858 0.2912 0.082 Uiso 1 1 calc R . . H26B H 0.3689 1.1251 0.2518 0.082 Uiso 1 1 calc R . . H26C H 0.4833 1.1012 0.2470 0.082 Uiso 1 1 calc R . . C9 C 0.31879(12) 0.7475(3) 0.27338(5) 0.0336(4) Uani 1 1 d . . . H9 H 0.3142 0.6014 0.2666 0.040 Uiso 1 1 calc R . . C10 C 0.32184(14) 0.7567(3) 0.32190(6) 0.0352(4) Uani 1 1 d . . . C25 C 0.31549(19) 0.9771(4) 0.33803(7) 0.0519(5) Uani 1 1 d . . . H25A H 0.2911 0.9750 0.3643 0.078 Uiso 1 1 calc R . . H25B H 0.2698 1.0551 0.3182 0.078 Uiso 1 1 calc R . . H25C H 0.3816 1.0384 0.3416 0.078 Uiso 1 1 calc R . . C11 C 0.22298(13) 0.8411(4) 0.24818(6) 0.0462(5) Uani 1 1 d . . . H11A H 0.1638 0.7863 0.2582 0.055 Uiso 1 1 calc R . . H11B H 0.2237 0.9879 0.2525 0.055 Uiso 1 1 calc R . . C12 C 0.21503(13) 0.7967(4) 0.20157(6) 0.0470(5) Uani 1 1 d . . . H12A H 0.1559 0.8659 0.1867 0.056 Uiso 1 1 calc R . . H12B H 0.2057 0.6509 0.1969 0.056 Uiso 1 1 calc R . . C13 C 0.30916(13) 0.8664(3) 0.18390(5) 0.0374(4) Uani 1 1 d . . . H13 H 0.3154 1.0144 0.1883 0.045 Uiso 1 1 calc R . . C14 C 0.40645(14) 0.7664(3) 0.20822(6) 0.0374(4) Uani 1 1 d . . . C27 C 0.40307(18) 0.5332(3) 0.20158(7) 0.0487(5) Uani 1 1 d . . . H27A H 0.3808 0.5038 0.1726 0.073 Uiso 1 1 calc R . . H27B H 0.3567 0.4734 0.2180 0.073 Uiso 1 1 calc R . . H27C H 0.4695 0.4770 0.2100 0.073 Uiso 1 1 calc R . . C15 C 0.49837(14) 0.8470(4) 0.18925(7) 0.0532(6) Uani 1 1 d . . . H15A H 0.5047 0.9930 0.1942 0.064 Uiso 1 1 calc R . . H15B H 0.5596 0.7825 0.2035 0.064 Uiso 1 1 calc R . . C16 C 0.49019(15) 0.8070(5) 0.14241(7) 0.0557(6) Uani 1 1 d . . . H16A H 0.5468 0.8724 0.1323 0.067 Uiso 1 1 calc R . . H16B H 0.4954 0.6610 0.1379 0.067 Uiso 1 1 calc R . . C17 C 0.39178(15) 0.8847(4) 0.11721(6) 0.0453(5) Uani 1 1 d . . . C18 C 0.29716(14) 0.8284(3) 0.13669(6) 0.0398(4) Uani 1 1 d . . . H18 H 0.2777 0.6861 0.1303 0.048 Uiso 1 1 calc R . . C19 C 0.22245(16) 0.9736(4) 0.11117(6) 0.0491(5) Uani 1 1 d . . . H19 H 0.1624 0.9912 0.1248 0.059 Uiso 1 1 calc R . . O19 O 0.27711(14) 1.1634(3) 0.11186(5) 0.0614(4) Uani 1 1 d . . . C20 C 0.19021(17) 0.9000(5) 0.06577(7) 0.0576(6) Uani 1 1 d . . . C29 C 0.1163(2) 1.0548(7) 0.04267(8) 0.0861(11) Uani 1 1 d . . . H29A H 0.0532 1.0490 0.0534 0.129 Uiso 1 1 calc R . . H29B H 0.1047 1.0230 0.0134 0.129 Uiso 1 1 calc R . . H29C H 0.1444 1.1897 0.0467 0.129 Uiso 1 1 calc R . . C30 C 0.1395(2) 0.6895(7) 0.06488(9) 0.0846(10) Uani 1 1 d . . . H30A H 0.1902 0.5866 0.0728 0.127 Uiso 1 1 calc R . . H30B H 0.1049 0.6618 0.0372 0.127 Uiso 1 1 calc R . . H30C H 0.0916 0.6881 0.0841 0.127 Uiso 1 1 calc R . . C21 C 0.28529(17) 0.8921(5) 0.04486(7) 0.0588(6) Uani 1 1 d . . . H21A H 0.2707 0.8115 0.0195 0.071 Uiso 1 1 calc R . . H21B H 0.3017 1.0297 0.0370 0.071 Uiso 1 1 calc R . . C22 C 0.37728(16) 0.8010(4) 0.07248(6) 0.0560(6) Uani 1 1 d . . . H22A H 0.4375 0.8304 0.0603 0.067 Uiso 1 1 calc R . . H22B H 0.3696 0.6537 0.0733 0.067 Uiso 1 1 calc R . . C28 C 0.38299(19) 1.1170(4) 0.11595(8) 0.0566(6) Uani 1 1 d . . . H28A H 0.4193 1.1762 0.1414 0.068 Uiso 1 1 calc R . . H28B H 0.4112 1.1714 0.0924 0.068 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 C1 0.0326(9) 0.0550(12) 0.0392(10) -0.0022(9) 0.0045(7) -0.0032(9) C2 0.0413(10) 0.0590(14) 0.0393(10) -0.0004(10) 0.0082(8) -0.0035(10) C3 0.0503(11) 0.0426(11) 0.0319(9) -0.0049(8) 0.0020(7) -0.0068(9) O3A 0.0693(9) 0.0507(9) 0.0330(7) -0.0039(7) 0.0001(6) -0.0097(8) C3A 0.0605(13) 0.0517(13) 0.0407(11) -0.0012(10) 0.0091(9) -0.0019(11) O3B 0.1064(14) 0.0752(13) 0.0516(9) -0.0080(10) 0.0191(9) -0.0395(12) C3B 0.122(2) 0.082(2) 0.0442(13) 0.0072(14) 0.0038(14) -0.010(2) C4 0.0414(10) 0.0431(11) 0.0404(10) -0.0040(9) -0.0022(7) -0.0007(9) C23 0.0644(14) 0.0590(14) 0.0471(11) -0.0101(11) -0.0043(10) -0.0176(12) C24 0.0525(12) 0.0680(16) 0.0555(13) 0.0098(12) -0.0044(10) 0.0119(12) C5 0.0337(9) 0.0341(9) 0.0418(10) -0.0055(8) 0.0006(7) -0.0023(8) C6 0.0299(9) 0.0595(13) 0.0574(12) 0.0010(11) -0.0011(8) -0.0030(10) C7 0.0296(9) 0.0602(14) 0.0535(11) 0.0031(11) 0.0073(8) -0.0009(9) C8 0.0307(9) 0.0344(9) 0.0472(10) 0.0013(8) 0.0075(7) -0.0013(8) C26 0.0659(14) 0.0395(11) 0.0606(13) -0.0023(11) 0.0149(11) -0.0132(11) C9 0.0299(8) 0.0317(9) 0.0397(9) -0.0013(8) 0.0065(7) 0.0009(7) C10 0.0338(9) 0.0332(9) 0.0382(9) -0.0036(8) 0.0045(7) 0.0008(8) C25 0.0659(13) 0.0409(11) 0.0496(12) -0.0063(10) 0.0115(10) 0.0089(10) C11 0.0330(9) 0.0646(14) 0.0427(10) 0.0081(10) 0.0115(7) 0.0115(10) C12 0.0315(9) 0.0698(15) 0.0407(10) 0.0077(10) 0.0089(7) 0.0047(9) C13 0.0348(9) 0.0369(9) 0.0426(10) 0.0043(8) 0.0124(7) 0.0063(8) C14 0.0325(9) 0.0352(10) 0.0461(10) 0.0027(8) 0.0112(7) 0.0043(8) C27 0.0570(12) 0.0386(11) 0.0511(12) -0.0001(9) 0.0106(9) 0.0137(10) C15 0.0332(10) 0.0702(16) 0.0586(12) 0.0081(12) 0.0144(8) 0.0024(11) C16 0.0412(10) 0.0704(16) 0.0611(13) 0.0090(12) 0.0250(9) 0.0097(11) C17 0.0422(10) 0.0479(12) 0.0499(11) 0.0023(10) 0.0205(9) 0.0045(9) C18 0.0368(9) 0.0411(10) 0.0438(10) 0.0028(9) 0.0137(8) 0.0051(8) C19 0.0468(11) 0.0590(14) 0.0448(11) 0.0082(11) 0.0175(9) 0.0171(10) O19 0.0794(11) 0.0446(9) 0.0639(10) 0.0100(8) 0.0227(8) 0.0192(9) C20 0.0500(12) 0.0814(18) 0.0437(11) 0.0078(12) 0.0144(9) 0.0130(12) C29 0.0709(17) 0.138(3) 0.0514(13) 0.0199(18) 0.0148(12) 0.042(2) C30 0.0734(18) 0.114(3) 0.0644(17) -0.0020(18) 0.0050(13) -0.0231(19) C21 0.0606(13) 0.0754(17) 0.0446(11) 0.0008(12) 0.0216(9) 0.0124(13) C22 0.0550(12) 0.0627(15) 0.0561(12) -0.0023(11) 0.0267(10) 0.0133(11) C28 0.0648(14) 0.0491(13) 0.0596(13) 0.0073(11) 0.0211(11) -0.0032(11) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.533(3) . ? C1 C10 1.543(3) . ? C1 H1A 0.9700 . ? C1 H1B 0.9700 . ? C2 C3 1.505(3) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 O3A 1.463(2) . ? C3 C4 1.531(3) . ? C3 H3 0.9800 . ? O3A C3A 1.330(3) . ? C3A O3B 1.197(3) . ? C3A C3B 1.496(3) . ? C3B H3B1 0.9600 . ? C3B H3B2 0.9600 . ? C3B H3B3 0.9600 . ? C4 C23 1.536(3) . ? C4 C24 1.541(3) . ? C4 C5 1.556(3) . ? C23 H23A 0.9600 . ? C23 H23B 0.9600 . ? C23 H23C 0.9600 . ? C24 H24A 0.9600 . ? C24 H24B 0.9600 . ? C24 H24C 0.9600 . ? C5 C6 1.534(3) . ? C5 C10 1.557(3) . ? C5 H5 0.9800 . ? C6 C7 1.521(3) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 C8 1.546(3) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 C26 1.545(3) . ? C8 C9 1.569(2) . ? C8 C14 1.587(3) . ? C26 H26A 0.9600 . ? C26 H26B 0.9600 . ? C26 H26C 0.9600 . ? C9 C11 1.534(2) . ? C9 C10 1.569(2) . ? C9 H9 0.9800 . ? C10 C25 1.540(3) . ? C25 H25A 0.9600 . ? C25 H25B 0.9600 . ? C25 H25C 0.9600 . ? C11 C12 1.527(3) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 C13 1.530(2) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 C18 1.535(2) . ? C13 C14 1.555(2) . ? C13 H13 0.9800 . ? C14 C27 1.540(3) . ? C14 C15 1.549(3) . ? C27 H27A 0.9600 . ? C27 H27B 0.9600 . ? C27 H27C 0.9600 . ? C15 C16 1.529(3) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 C17 1.522(3) . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C17 C28 1.524(3) . ? C17 C22 1.535(3) . ? C17 C18 1.543(2) . ? C18 C19 1.524(3) . ? C18 H18 0.9800 . ? C19 O19 1.438(3) . ? C19 C20 1.546(3) . ? C19 H19 0.9800 . ? O19 C28 1.432(3) . ? C20 C29 1.526(4) . ? C20 C21 1.531(3) . ? C20 C30 1.533(5) . ? C29 H29A 0.9600 . ? C29 H29B 0.9600 . ? C29 H29C 0.9600 . ? C30 H30A 0.9600 . ? C30 H30B 0.9600 . ? C30 H30C 0.9600 . ? C21 C22 1.524(3) . ? C21 H21A 0.9700 . ? C21 H21B 0.9700 . ? C22 H22A 0.9700 . ? C22 H22B 0.9700 . ? C28 H28A 0.9700 . ? C28 H28B 0.9700 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C10 113.04(15) . . ? C2 C1 H1A 109.0 . . ? C10 C1 H1A 109.0 . . ? C2 C1 H1B 109.0 . . ? C10 C1 H1B 109.0 . . ? H1A C1 H1B 107.8 . . ? C3 C2 C1 110.15(15) . . ? C3 C2 H2A 109.6 . . ? C1 C2 H2A 109.6 . . ? C3 C2 H2B 109.6 . . ? C1 C2 H2B 109.6 . . ? H2A C2 H2B 108.1 . . ? O3A C3 C2 109.77(15) . . ? O3A C3 C4 107.14(14) . . ? C2 C3 C4 115.10(18) . . ? O3A C3 H3 108.2 . . ? C2 C3 H3 108.2 . . ? C4 C3 H3 108.2 . . ? C3A O3A C3 118.74(16) . . ? O3B C3A O3A 123.89(19) . . ? O3B C3A C3B 124.5(2) . . ? O3A C3A C3B 111.6(2) . . ? C3A C3B H3B1 109.5 . . ? C3A C3B H3B2 109.5 . . ? H3B1 C3B H3B2 109.5 . . ? C3A C3B H3B3 109.5 . . ? H3B1 C3B H3B3 109.5 . . ? H3B2 C3B H3B3 109.5 . . ? C3 C4 C23 111.56(17) . . ? C3 C4 C24 107.24(19) . . ? C23 C4 C24 108.49(17) . . ? C3 C4 C5 106.69(14) . . ? C23 C4 C5 114.27(18) . . ? C24 C4 C5 108.32(16) . . ? C4 C23 H23A 109.5 . . ? C4 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C4 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C4 C24 H24A 109.5 . . ? C4 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C4 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C6 C5 C4 113.41(15) . . ? C6 C5 C10 110.67(17) . . ? C4 C5 C10 117.90(15) . . ? C6 C5 H5 104.4 . . ? C4 C5 H5 104.4 . . ? C10 C5 H5 104.4 . . ? C7 C6 C5 110.56(16) . . ? C7 C6 H6A 109.5 . . ? C5 C6 H6A 109.5 . . ? C7 C6 H6B 109.5 . . ? C5 C6 H6B 109.5 . . ? H6A C6 H6B 108.1 . . ? C6 C7 C8 113.69(17) . . ? C6 C7 H7A 108.8 . . ? C8 C7 H7A 108.8 . . ? C6 C7 H7B 108.8 . . ? C8 C7 H7B 108.8 . . ? H7A C7 H7B 107.7 . . ? C26 C8 C7 107.33(19) . . ? C26 C8 C9 111.43(17) . . ? C7 C8 C9 108.43(15) . . ? C26 C8 C14 109.85(17) . . ? C7 C8 C14 110.43(15) . . ? C9 C8 C14 109.35(14) . . ? C8 C26 H26A 109.5 . . ? C8 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C8 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? C11 C9 C8 110.65(15) . . ? C11 C9 C10 114.07(13) . . ? C8 C9 C10 116.77(14) . . ? C11 C9 H9 104.6 . . ? C8 C9 H9 104.6 . . ? C10 C9 H9 104.6 . . ? C25 C10 C1 107.13(16) . . ? C25 C10 C5 114.65(17) . . ? C1 C10 C5 106.99(15) . . ? C25 C10 C9 112.50(15) . . ? C1 C10 C9 108.99(14) . . ? C5 C10 C9 106.37(14) . . ? C10 C25 H25A 109.5 . . ? C10 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? C10 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? C12 C11 C9 112.02(15) . . ? C12 C11 H11A 109.2 . . ? C9 C11 H11A 109.2 . . ? C12 C11 H11B 109.2 . . ? C9 C11 H11B 109.2 . . ? H11A C11 H11B 107.9 . . ? C11 C12 C13 112.37(17) . . ? C11 C12 H12A 109.1 . . ? C13 C12 H12A 109.1 . . ? C11 C12 H12B 109.1 . . ? C13 C12 H12B 109.1 . . ? H12A C12 H12B 107.9 . . ? C12 C13 C18 111.24(15) . . ? C12 C13 C14 110.78(15) . . ? C18 C13 C14 112.76(14) . . ? C12 C13 H13 107.3 . . ? C18 C13 H13 107.3 . . ? C14 C13 H13 107.3 . . ? C27 C14 C15 106.80(18) . . ? C27 C14 C13 109.97(18) . . ? C15 C14 C13 107.84(15) . . ? C27 C14 C8 111.34(16) . . ? C15 C14 C8 111.36(16) . . ? C13 C14 C8 109.43(14) . . ? C14 C27 H27A 109.5 . . ? C14 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? C14 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? C16 C15 C14 113.51(18) . . ? C16 C15 H15A 108.9 . . ? C14 C15 H15A 108.9 . . ? C16 C15 H15B 108.9 . . ? C14 C15 H15B 108.9 . . ? H15A C15 H15B 107.7 . . ? C17 C16 C15 113.45(17) . . ? C17 C16 H16A 108.9 . . ? C15 C16 H16A 108.9 . . ? C17 C16 H16B 108.9 . . ? C15 C16 H16B 108.9 . . ? H16A C16 H16B 107.7 . . ? C16 C17 C28 113.8(2) . . ? C16 C17 C22 111.06(17) . . ? C28 C17 C22 109.4(2) . . ? C16 C17 C18 113.18(17) . . ? C28 C17 C18 100.62(17) . . ? C22 C17 C18 108.17(18) . . ? C19 C18 C13 113.48(15) . . ? C19 C18 C17 97.88(16) . . ? C13 C18 C17 113.94(16) . . ? C19 C18 H18 110.3 . . ? C13 C18 H18 110.3 . . ? C17 C18 H18 110.3 . . ? O19 C19 C18 103.99(16) . . ? O19 C19 C20 110.41(18) . . ? C18 C19 C20 112.60(18) . . ? O19 C19 H19 109.9 . . ? C18 C19 H19 109.9 . . ? C20 C19 H19 109.9 . . ? C28 O19 C19 108.06(17) . . ? C29 C20 C21 108.8(2) . . ? C29 C20 C30 109.7(2) . . ? C21 C20 C30 110.9(2) . . ? C29 C20 C19 108.9(2) . . ? C21 C20 C19 107.83(18) . . ? C30 C20 C19 110.7(2) . . ? C20 C29 H29A 109.5 . . ? C20 C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? C20 C29 H29C 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? C20 C30 H30A 109.5 . . ? C20 C30 H30B 109.5 . . ? H30A C30 H30B 109.5 . . ? C20 C30 H30C 109.5 . . ? H30A C30 H30C 109.5 . . ? H30B C30 H30C 109.5 . . ? C22 C21 C20 113.61(17) . . ? C22 C21 H21A 108.8 . . ? C20 C21 H21A 108.8 . . ? C22 C21 H21B 108.8 . . ? C20 C21 H21B 108.8 . . ? H21A C21 H21B 107.7 . . ? C21 C22 C17 112.81(18) . . ? C21 C22 H22A 109.0 . . ? C17 C22 H22A 109.0 . . ? C21 C22 H22B 109.0 . . ? C17 C22 H22B 109.0 . . ? H22A C22 H22B 107.8 . . ? O19 C28 C17 106.5(2) . . ? O19 C28 H28A 110.4 . . ? C17 C28 H28A 110.4 . . ? O19 C28 H28B 110.4 . . ? C17 C28 H28B 110.4 . . ? H28A C28 H28B 108.6 . . ? 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 C10 C1 C2 C3 -58.0(2) . . . . ? C1 C2 C3 O3A 178.98(17) . . . . ? C1 C2 C3 C4 58.0(2) . . . . ? C2 C3 O3A C3A 92.0(2) . . . . ? C4 C3 O3A C3A -142.38(19) . . . . ? C3 O3A C3A O3B -4.9(3) . . . . ? C3 O3A C3A C3B 174.8(2) . . . . ? O3A C3 C4 C23 -49.5(2) . . . . ? C2 C3 C4 C23 72.9(2) . . . . ? O3A C3 C4 C24 69.2(2) . . . . ? C2 C3 C4 C24 -168.48(17) . . . . ? O3A C3 C4 C5 -174.95(16) . . . . ? C2 C3 C4 C5 -52.6(2) . . . . ? C3 C4 C5 C6 -177.24(18) . . . . ? C23 C4 C5 C6 59.0(2) . . . . ? C24 C4 C5 C6 -62.1(2) . . . . ? C3 C4 C5 C10 51.1(2) . . . . ? C23 C4 C5 C10 -72.7(2) . . . . ? C24 C4 C5 C10 166.29(18) . . . . ? C4 C5 C6 C7 162.17(18) . . . . ? C10 C5 C6 C7 -62.7(2) . . . . ? C5 C6 C7 C8 58.3(3) . . . . ? C6 C7 C8 C26 70.6(2) . . . . ? C6 C7 C8 C9 -49.8(2) . . . . ? C6 C7 C8 C14 -169.63(17) . . . . ? C26 C8 C9 C11 64.5(2) . . . . ? C7 C8 C9 C11 -177.57(17) . . . . ? C14 C8 C9 C11 -57.1(2) . . . . ? C26 C8 C9 C10 -68.2(2) . . . . ? C7 C8 C9 C10 49.7(2) . . . . ? C14 C8 C9 C10 170.17(15) . . . . ? C2 C1 C10 C25 -69.9(2) . . . . ? C2 C1 C10 C5 53.5(2) . . . . ? C2 C1 C10 C9 168.11(17) . . . . ? C6 C5 C10 C25 -66.6(2) . . . . ? C4 C5 C10 C25 66.3(2) . . . . ? C6 C5 C10 C1 174.81(16) . . . . ? C4 C5 C10 C1 -52.3(2) . . . . ? C6 C5 C10 C9 58.4(2) . . . . ? C4 C5 C10 C9 -168.71(15) . . . . ? C11 C9 C10 C25 -59.0(2) . . . . ? C8 C9 C10 C25 72.1(2) . . . . ? C11 C9 C10 C1 59.6(2) . . . . ? C8 C9 C10 C1 -169.22(16) . . . . ? C11 C9 C10 C5 174.66(16) . . . . ? C8 C9 C10 C5 -54.2(2) . . . . ? C8 C9 C11 C12 55.6(2) . . . . ? C10 C9 C11 C12 -170.35(18) . . . . ? C9 C11 C12 C13 -55.2(3) . . . . ? C11 C12 C13 C18 -177.52(18) . . . . ? C11 C12 C13 C14 56.2(2) . . . . ? C12 C13 C14 C27 65.0(2) . . . . ? C18 C13 C14 C27 -60.4(2) . . . . ? C12 C13 C14 C15 -178.90(18) . . . . ? C18 C13 C14 C15 55.7(2) . . . . ? C12 C13 C14 C8 -57.6(2) . . . . ? C18 C13 C14 C8 176.99(15) . . . . ? C26 C8 C14 C27 173.75(19) . . . . ? C7 C8 C14 C27 55.6(2) . . . . ? C9 C8 C14 C27 -63.7(2) . . . . ? C26 C8 C14 C15 54.7(2) . . . . ? C7 C8 C14 C15 -63.5(2) . . . . ? C9 C8 C14 C15 177.25(17) . . . . ? C26 C8 C14 C13 -64.5(2) . . . . ? C7 C8 C14 C13 177.35(16) . . . . ? C9 C8 C14 C13 58.12(19) . . . . ? C27 C14 C15 C16 61.4(2) . . . . ? C13 C14 C15 C16 -56.7(3) . . . . ? C8 C14 C15 C16 -176.82(19) . . . . ? C14 C15 C16 C17 53.3(3) . . . . ? C15 C16 C17 C28 68.2(3) . . . . ? C15 C16 C17 C22 -167.8(2) . . . . ? C15 C16 C17 C18 -45.9(3) . . . . ? C12 C13 C18 C19 72.2(2) . . . . ? C14 C13 C18 C19 -162.65(17) . . . . ? C12 C13 C18 C17 -176.92(18) . . . . ? C14 C13 C18 C17 -51.8(2) . . . . ? C16 C17 C18 C19 165.7(2) . . . . ? C28 C17 C18 C19 43.8(2) . . . . ? C22 C17 C18 C19 -70.8(2) . . . . ? C16 C17 C18 C13 45.6(3) . . . . ? C28 C17 C18 C13 -76.3(2) . . . . ? C22 C17 C18 C13 169.07(18) . . . . ? C13 C18 C19 O19 75.37(18) . . . . ? C17 C18 C19 O19 -45.08(18) . . . . ? C13 C18 C19 C20 -165.08(17) . . . . ? C17 C18 C19 C20 74.5(2) . . . . ? C18 C19 O19 C28 28.6(2) . . . . ? C20 C19 O19 C28 -92.4(2) . . . . ? O19 C19 C20 C29 -63.9(2) . . . . ? C18 C19 C20 C29 -179.7(2) . . . . ? O19 C19 C20 C21 54.0(2) . . . . ? C18 C19 C20 C21 -61.8(3) . . . . ? O19 C19 C20 C30 175.4(2) . . . . ? C18 C19 C20 C30 59.7(2) . . . . ? C29 C20 C21 C22 160.7(3) . . . . ? C30 C20 C21 C22 -78.6(3) . . . . ? C19 C20 C21 C22 42.8(3) . . . . ? C20 C21 C22 C17 -45.2(3) . . . . ? C16 C17 C22 C21 -174.1(2) . . . . ? C28 C17 C22 C21 -47.6(3) . . . . ? C18 C17 C22 C21 61.1(3) . . . . ? C19 O19 C28 C17 0.7(2) . . . . ? C16 C17 C28 O19 -150.38(16) . . . . ? C22 C17 C28 O19 84.7(2) . . . . ? C18 C17 C28 O19 -29.0(2) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.184 _refine_diff_density_min -0.126 _refine_diff_density_rms 0.027 #====END data_rsrx54 _database_code_depnum_ccdc_archive 'CCDC 699290' _audit_creation_method SHELXL-97 _chemical_name_systematic ; A-neo-18\a-olean-3(5)-en-28,19\b-olide ; _chemical_name_common ? _chemical_melting_point 566 _chemical_formula_moiety 'C30 H46 O2' _chemical_formula_sum 'C30 H46 O2' _chemical_formula_weight 438.67 _chemical_absolute_configuration syn 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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M C2 _symmetry_space_group_name_Hall 'C 2y' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z' _cell_length_a 13.2214(4) _cell_length_b 6.4962(2) _cell_length_c 29.8420(9) _cell_angle_alpha 90.00 _cell_angle_beta 93.615(2) _cell_angle_gamma 90.00 _cell_volume 2558.00(13) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3298 _cell_measurement_theta_min 2.7356 _cell_measurement_theta_max 19.4413 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.139 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 968 _exptl_absorpt_coefficient_mu 0.069 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.909 _exptl_absorpt_correction_T_max 0.999 _exptl_absorpt_process_details '(SADABS; Sheldrick, 2000)' _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 'Bruker APEX CCD area-detector' _diffrn_measurement_method '\f and \w scans' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 22819 _diffrn_reflns_av_R_equivalents 0.0612 _diffrn_reflns_av_sigmaI/netI 0.0531 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -36 _diffrn_reflns_limit_l_max 35 _diffrn_reflns_theta_min 2.05 _diffrn_reflns_theta_max 25.76 _reflns_number_total 2655 _reflns_number_gt 1677 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'SMART (Bruker, 2003)' _computing_cell_refinement 'SAINT (Bruker, 2003)' _computing_data_reduction 'SAINT (Bruker, 2003)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement SHELXL-97 _computing_molecular_graphics 'PLATON (Spek, 2005)' _computing_publication_material SHELXL-97 _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^)+(0.0606P)^2^+0.2469P] 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 riding _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 1(2) _refine_ls_number_reflns 2655 _refine_ls_number_parameters 296 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0971 _refine_ls_R_factor_gt 0.0462 _refine_ls_wR_factor_ref 0.1158 _refine_ls_wR_factor_gt 0.0958 _refine_ls_goodness_of_fit_ref 0.994 _refine_ls_restrained_S_all 0.994 _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 0.6521(3) 0.5112(6) 0.85987(11) 0.0492(9) Uani 1 1 d . . . H1A H 0.5828 0.5607 0.8595 0.059 Uiso 1 1 calc R . . H1B H 0.6548 0.3944 0.8397 0.059 Uiso 1 1 calc R . . C2 C 0.6909(3) 0.4509(6) 0.90790(12) 0.0568(10) Uani 1 1 d . . . H2A H 0.6572 0.5298 0.9302 0.068 Uiso 1 1 calc R . . H2B H 0.6810 0.3053 0.9133 0.068 Uiso 1 1 calc R . . C3 C 0.8042(3) 0.5051(6) 0.90827(12) 0.0500(9) Uani 1 1 d . . . C4 C 0.8792(3) 0.4289(6) 0.94373(13) 0.0615(11) Uani 1 1 d . . . H4 H 0.9442 0.4953 0.9389 0.074 Uiso 1 1 calc R . . C5 C 0.8208(2) 0.6275(5) 0.87375(12) 0.0430(9) Uani 1 1 d . . . C6 C 0.9185(2) 0.7138(6) 0.85992(12) 0.0486(9) Uani 1 1 d . . . H6A H 0.9744 0.6460 0.8766 0.058 Uiso 1 1 calc R . . H6B H 0.9216 0.8594 0.8670 0.058 Uiso 1 1 calc R . . C7 C 0.9289(2) 0.6840(6) 0.80982(11) 0.0440(9) Uani 1 1 d . . . H7A H 0.9333 0.5378 0.8036 0.053 Uiso 1 1 calc R . . H7B H 0.9917 0.7471 0.8018 0.053 Uiso 1 1 calc R . . C8 C 0.8407(2) 0.7759(5) 0.78000(11) 0.0353(8) Uani 1 1 d . . . C9 C 0.7406(2) 0.6763(5) 0.79507(10) 0.0349(8) Uani 1 1 d . . . H9 H 0.7474 0.5295 0.7883 0.042 Uiso 1 1 calc R . . C10 C 0.7240(2) 0.6837(5) 0.84597(11) 0.0405(8) Uani 1 1 d . . . C11 C 0.6482(2) 0.7466(6) 0.76566(11) 0.0456(9) Uani 1 1 d . . . H11A H 0.5882 0.6774 0.7752 0.055 Uiso 1 1 calc R . . H11B H 0.6387 0.8935 0.7694 0.055 Uiso 1 1 calc R . . C12 C 0.6607(2) 0.6997(6) 0.71617(11) 0.0455(9) Uani 1 1 d . . . H12A H 0.6025 0.7525 0.6983 0.055 Uiso 1 1 calc R . . H12B H 0.6629 0.5518 0.7119 0.055 Uiso 1 1 calc R . . C13 C 0.7572(2) 0.7957(5) 0.69986(10) 0.0348(8) Uani 1 1 d . . . H13 H 0.7518 0.9448 0.7041 0.042 Uiso 1 1 calc R . . C14 C 0.8525(2) 0.7229(5) 0.72875(11) 0.0357(8) Uani 1 1 d . . . C15 C 0.9449(2) 0.8355(6) 0.71046(12) 0.0499(10) Uani 1 1 d . . . H15A H 0.9363 0.9827 0.7142 0.060 Uiso 1 1 calc R . . H15B H 1.0057 0.7948 0.7282 0.060 Uiso 1 1 calc R . . C16 C 0.9592(2) 0.7902(6) 0.66120(12) 0.0520(10) Uani 1 1 d . . . H16A H 1.0147 0.8728 0.6514 0.062 Uiso 1 1 calc R . . H16B H 0.9772 0.6464 0.6580 0.062 Uiso 1 1 calc R . . C17 C 0.8645(2) 0.8354(5) 0.63138(11) 0.0401(8) Uani 1 1 d . . . C18 C 0.7655(2) 0.7586(5) 0.64969(11) 0.0377(8) Uani 1 1 d . . . H18 H 0.7558 0.6121 0.6428 0.045 Uiso 1 1 calc R . . C19 C 0.6922(3) 0.8884(5) 0.61989(12) 0.0447(9) Uani 1 1 d . . . H19 H 0.6258 0.8958 0.6327 0.054 Uiso 1 1 calc R . . C20 C 0.6808(3) 0.8177(6) 0.57071(12) 0.0491(9) Uani 1 1 d . . . C21 C 0.7849(3) 0.8280(6) 0.55130(11) 0.0511(10) Uani 1 1 d . . . H21A H 0.7834 0.7462 0.5241 0.061 Uiso 1 1 calc R . . H21B H 0.7985 0.9694 0.5431 0.061 Uiso 1 1 calc R . . C22 C 0.8713(3) 0.7517(6) 0.58337(11) 0.0494(10) Uani 1 1 d . . . H22A H 0.9354 0.7935 0.5721 0.059 Uiso 1 1 calc R . . H22B H 0.8700 0.6025 0.5842 0.059 Uiso 1 1 calc R . . C23 C 0.8493(4) 0.4900(11) 0.98992(15) 0.1097(19) Uani 1 1 d . . . H23A H 0.8530 0.6370 0.9930 0.165 Uiso 1 1 calc R . . H23B H 0.8946 0.4268 1.0123 0.165 Uiso 1 1 calc R . . H23C H 0.7813 0.4451 0.9939 0.165 Uiso 1 1 calc R . . C24 C 0.8948(4) 0.2015(9) 0.94066(18) 0.111(2) Uani 1 1 d . . . H24A H 0.8323 0.1319 0.9454 0.167 Uiso 1 1 calc R . . H24B H 0.9457 0.1591 0.9631 0.167 Uiso 1 1 calc R . . H24C H 0.9163 0.1674 0.9114 0.167 Uiso 1 1 calc R . . C25 C 0.6826(3) 0.8897(6) 0.86296(13) 0.0578(11) Uani 1 1 d . . . H25A H 0.6234 0.9284 0.8446 0.087 Uiso 1 1 calc R . . H25B H 0.7334 0.9944 0.8613 0.087 Uiso 1 1 calc R . . H25C H 0.6652 0.8743 0.8935 0.087 Uiso 1 1 calc R . . C26 C 0.8410(3) 1.0118(5) 0.78696(12) 0.0501(10) Uani 1 1 d . . . H26A H 0.7842 1.0714 0.7700 0.075 Uiso 1 1 calc R . . H26B H 0.9027 1.0684 0.7769 0.075 Uiso 1 1 calc R . . H26C H 0.8364 1.0420 0.8183 0.075 Uiso 1 1 calc R . . C27 C 0.8691(3) 0.4902(5) 0.72195(12) 0.0460(9) Uani 1 1 d . . . H27A H 0.8196 0.4143 0.7373 0.069 Uiso 1 1 calc R . . H27B H 0.9358 0.4531 0.7338 0.069 Uiso 1 1 calc R . . H27C H 0.8624 0.4585 0.6905 0.069 Uiso 1 1 calc R . . C28 C 0.8425(3) 1.0634(6) 0.62675(12) 0.0497(10) Uani 1 1 d . . . C29 C 0.6076(3) 0.9619(8) 0.54459(13) 0.0723(13) Uani 1 1 d . . . H29A H 0.5409 0.9460 0.5551 0.108 Uiso 1 1 calc R . . H29B H 0.6062 0.9288 0.5132 0.108 Uiso 1 1 calc R . . H29C H 0.6296 1.1017 0.5490 0.108 Uiso 1 1 calc R . . C30 C 0.6384(3) 0.5986(7) 0.56866(13) 0.0678(12) Uani 1 1 d . . . H30A H 0.6906 0.5033 0.5786 0.102 Uiso 1 1 calc R . . H30B H 0.6151 0.5668 0.5383 0.102 Uiso 1 1 calc R . . H30C H 0.5828 0.5883 0.5878 0.102 Uiso 1 1 calc R . . O19 O 0.7417(2) 1.0921(4) 0.62139(8) 0.0529(7) Uani 1 1 d . . . O28 O 0.9005(2) 1.2052(4) 0.62627(9) 0.0698(8) 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 0.042(2) 0.061(2) 0.045(2) 0.0021(19) 0.0041(18) -0.0130(18) C2 0.068(3) 0.063(2) 0.041(2) 0.0038(18) 0.0092(19) -0.007(2) C3 0.047(2) 0.057(2) 0.046(2) -0.001(2) 0.0037(18) 0.0008(18) C4 0.062(3) 0.073(3) 0.048(3) 0.003(2) -0.002(2) 0.002(2) C5 0.036(2) 0.054(2) 0.039(2) -0.0010(17) 0.0006(17) -0.0052(16) C6 0.037(2) 0.058(2) 0.050(2) 0.0008(19) -0.0035(17) -0.0055(17) C7 0.0304(19) 0.055(2) 0.046(2) 0.0022(18) 0.0025(16) -0.0051(16) C8 0.0307(19) 0.0325(17) 0.043(2) 0.0018(14) 0.0002(16) -0.0044(14) C9 0.0278(18) 0.0379(17) 0.039(2) 0.0014(15) -0.0006(15) -0.0065(14) C10 0.0340(19) 0.0477(19) 0.040(2) 0.0026(16) 0.0009(16) -0.0037(16) C11 0.032(2) 0.066(2) 0.039(2) 0.0058(17) 0.0053(16) -0.0012(17) C12 0.031(2) 0.063(2) 0.042(2) 0.0043(19) 0.0023(16) -0.0045(17) C13 0.0337(19) 0.0349(17) 0.036(2) 0.0027(15) 0.0054(15) 0.0009(14) C14 0.0306(18) 0.0330(17) 0.044(2) 0.0035(15) 0.0074(15) -0.0024(14) C15 0.039(2) 0.062(2) 0.050(3) 0.0100(19) 0.0086(18) -0.0099(18) C16 0.039(2) 0.064(2) 0.054(3) 0.0060(19) 0.0149(19) -0.0067(18) C17 0.042(2) 0.0383(18) 0.042(2) 0.0025(16) 0.0116(17) -0.0023(15) C18 0.0381(19) 0.0367(18) 0.039(2) 0.0024(15) 0.0078(16) -0.0004(15) C19 0.045(2) 0.050(2) 0.039(2) 0.0045(17) 0.0093(17) 0.0079(17) C20 0.051(2) 0.060(2) 0.037(2) 0.0016(17) 0.0063(18) 0.0026(18) C21 0.063(2) 0.055(2) 0.037(2) -0.0018(17) 0.0156(19) -0.0018(19) C22 0.048(2) 0.048(2) 0.054(3) -0.0035(17) 0.0191(19) 0.0015(17) C23 0.121(4) 0.150(5) 0.056(3) -0.011(4) -0.009(3) 0.027(4) C24 0.132(5) 0.092(4) 0.103(4) -0.011(3) -0.041(4) 0.039(3) C25 0.056(3) 0.062(3) 0.057(3) -0.005(2) 0.011(2) 0.007(2) C26 0.053(2) 0.044(2) 0.054(3) -0.0003(18) 0.0090(19) -0.0091(17) C27 0.048(2) 0.0424(19) 0.048(2) 0.0013(17) 0.0029(17) 0.0101(16) C28 0.067(3) 0.046(2) 0.038(2) -0.0007(16) 0.018(2) -0.001(2) C29 0.074(3) 0.099(4) 0.043(3) 0.009(2) 0.001(2) 0.018(3) C30 0.067(3) 0.084(3) 0.053(3) -0.008(2) 0.007(2) -0.017(2) O19 0.0714(19) 0.0401(13) 0.0482(16) 0.0045(11) 0.0108(14) 0.0108(12) O28 0.096(2) 0.0487(16) 0.0669(19) -0.0018(14) 0.0261(15) -0.0231(16) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.542(5) . ? C1 C10 1.543(5) . ? C1 H1A 0.9700 . ? C1 H1B 0.9700 . ? C2 C3 1.538(5) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 C5 1.331(5) . ? C3 C4 1.489(5) . ? C4 C24 1.495(7) . ? C4 C23 1.511(6) . ? C4 H4 0.9800 . ? C5 C6 1.489(5) . ? C5 C10 1.525(5) . ? C6 C7 1.522(4) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 C8 1.542(4) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 C26 1.546(5) . ? C8 C9 1.564(4) . ? C8 C14 1.585(4) . ? C9 C11 1.528(4) . ? C9 C10 1.549(4) . ? C9 H9 0.9800 . ? C10 C25 1.544(5) . ? C11 C12 1.527(4) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 C13 1.527(4) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 C18 1.527(4) . ? C13 C14 1.554(4) . ? C13 H13 0.9800 . ? C14 C27 1.543(4) . ? C14 C15 1.552(4) . ? C15 C16 1.523(5) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 C17 1.518(5) . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C17 C28 1.514(5) . ? C17 C18 1.533(4) . ? C17 C22 1.540(5) . ? C18 C19 1.528(4) . ? C18 H18 0.9800 . ? C19 O19 1.475(4) . ? C19 C20 1.536(5) . ? C19 H19 0.9800 . ? C20 C29 1.525(5) . ? C20 C21 1.529(5) . ? C20 C30 1.529(6) . ? C21 C22 1.525(5) . ? C21 H21A 0.9700 . ? C21 H21B 0.9700 . ? C22 H22A 0.9700 . ? C22 H22B 0.9700 . ? C23 H23A 0.9600 . ? C23 H23B 0.9600 . ? C23 H23C 0.9600 . ? C24 H24A 0.9600 . ? C24 H24B 0.9600 . ? C24 H24C 0.9600 . ? C25 H25A 0.9600 . ? C25 H25B 0.9600 . ? C25 H25C 0.9600 . ? C26 H26A 0.9600 . ? C26 H26B 0.9600 . ? C26 H26C 0.9600 . ? C27 H27A 0.9600 . ? C27 H27B 0.9600 . ? C27 H27C 0.9600 . ? C28 O28 1.199(4) . ? C28 O19 1.346(4) . ? C29 H29A 0.9600 . ? C29 H29B 0.9600 . ? C29 H29C 0.9600 . ? C30 H30A 0.9600 . ? C30 H30B 0.9600 . ? C30 H30C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C10 105.1(3) . . ? C2 C1 H1A 110.7 . . ? C10 C1 H1A 110.7 . . ? C2 C1 H1B 110.7 . . ? C10 C1 H1B 110.7 . . ? H1A C1 H1B 108.8 . . ? C3 C2 C1 102.4(3) . . ? C3 C2 H2A 111.3 . . ? C1 C2 H2A 111.3 . . ? C3 C2 H2B 111.3 . . ? C1 C2 H2B 111.3 . . ? H2A C2 H2B 109.2 . . ? C5 C3 C4 127.8(3) . . ? C5 C3 C2 109.9(3) . . ? C4 C3 C2 122.3(3) . . ? C3 C4 C24 111.9(4) . . ? C3 C4 C23 111.1(4) . . ? C24 C4 C23 111.1(5) . . ? C3 C4 H4 107.5 . . ? C24 C4 H4 107.5 . . ? C23 C4 H4 107.5 . . ? C3 C5 C6 128.9(3) . . ? C3 C5 C10 112.9(3) . . ? C6 C5 C10 118.2(3) . . ? C5 C6 C7 111.0(3) . . ? C5 C6 H6A 109.4 . . ? C7 C6 H6A 109.4 . . ? C5 C6 H6B 109.4 . . ? C7 C6 H6B 109.4 . . ? H6A C6 H6B 108.0 . . ? C6 C7 C8 113.9(3) . . ? C6 C7 H7A 108.8 . . ? C8 C7 H7A 108.8 . . ? C6 C7 H7B 108.8 . . ? C8 C7 H7B 108.8 . . ? H7A C7 H7B 107.7 . . ? C7 C8 C26 108.1(3) . . ? C7 C8 C9 107.3(3) . . ? C26 C8 C9 111.5(3) . . ? C7 C8 C14 110.9(3) . . ? C26 C8 C14 110.2(3) . . ? C9 C8 C14 108.9(2) . . ? C11 C9 C10 113.4(3) . . ? C11 C9 C8 111.8(3) . . ? C10 C9 C8 116.3(2) . . ? C11 C9 H9 104.6 . . ? C10 C9 H9 104.6 . . ? C8 C9 H9 104.6 . . ? C5 C10 C1 101.0(3) . . ? C5 C10 C25 109.4(3) . . ? C1 C10 C25 107.7(3) . . ? C5 C10 C9 111.1(3) . . ? C1 C10 C9 111.6(3) . . ? C25 C10 C9 115.1(3) . . ? C12 C11 C9 111.4(3) . . ? C12 C11 H11A 109.4 . . ? C9 C11 H11A 109.4 . . ? C12 C11 H11B 109.4 . . ? C9 C11 H11B 109.4 . . ? H11A C11 H11B 108.0 . . ? C11 C12 C13 111.7(3) . . ? C11 C12 H12A 109.3 . . ? C13 C12 H12A 109.3 . . ? C11 C12 H12B 109.3 . . ? C13 C12 H12B 109.3 . . ? H12A C12 H12B 107.9 . . ? C18 C13 C12 111.2(3) . . ? C18 C13 C14 113.0(2) . . ? C12 C13 C14 111.3(3) . . ? C18 C13 H13 107.0 . . ? C12 C13 H13 107.0 . . ? C14 C13 H13 107.0 . . ? C27 C14 C15 107.1(3) . . ? C27 C14 C13 110.0(3) . . ? C15 C14 C13 106.9(3) . . ? C27 C14 C8 111.3(3) . . ? C15 C14 C8 111.4(3) . . ? C13 C14 C8 110.1(2) . . ? C16 C15 C14 113.4(3) . . ? C16 C15 H15A 108.9 . . ? C14 C15 H15A 108.9 . . ? C16 C15 H15B 108.9 . . ? C14 C15 H15B 108.9 . . ? H15A C15 H15B 107.7 . . ? C17 C16 C15 112.4(3) . . ? C17 C16 H16A 109.1 . . ? C15 C16 H16A 109.1 . . ? C17 C16 H16B 109.1 . . ? C15 C16 H16B 109.1 . . ? H16A C16 H16B 107.9 . . ? C28 C17 C16 112.9(3) . . ? C28 C17 C18 100.9(3) . . ? C16 C17 C18 114.8(3) . . ? C28 C17 C22 106.4(3) . . ? C16 C17 C22 112.5(3) . . ? C18 C17 C22 108.5(3) . . ? C13 C18 C19 113.7(3) . . ? C13 C18 C17 114.4(3) . . ? C19 C18 C17 97.9(3) . . ? C13 C18 H18 110.1 . . ? C19 C18 H18 110.1 . . ? C17 C18 H18 110.1 . . ? O19 C19 C18 102.3(3) . . ? O19 C19 C20 108.3(3) . . ? C18 C19 C20 114.3(3) . . ? O19 C19 H19 110.5 . . ? C18 C19 H19 110.5 . . ? C20 C19 H19 110.5 . . ? C29 C20 C21 109.7(3) . . ? C29 C20 C30 109.4(3) . . ? C21 C20 C30 111.2(3) . . ? C29 C20 C19 109.0(3) . . ? C21 C20 C19 108.2(3) . . ? C30 C20 C19 109.3(3) . . ? C22 C21 C20 113.8(3) . . ? C22 C21 H21A 108.8 . . ? C20 C21 H21A 108.8 . . ? C22 C21 H21B 108.8 . . ? C20 C21 H21B 108.8 . . ? H21A C21 H21B 107.7 . . ? C21 C22 C17 112.6(3) . . ? C21 C22 H22A 109.1 . . ? C17 C22 H22A 109.1 . . ? C21 C22 H22B 109.1 . . ? C17 C22 H22B 109.1 . . ? H22A C22 H22B 107.8 . . ? C4 C23 H23A 109.5 . . ? C4 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C4 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C4 C24 H24A 109.5 . . ? C4 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C4 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C10 C25 H25A 109.5 . . ? C10 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? C10 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? C8 C26 H26A 109.5 . . ? C8 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C8 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? C14 C27 H27A 109.5 . . ? C14 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? C14 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? O28 C28 O19 121.5(3) . . ? O28 C28 C17 129.3(4) . . ? O19 C28 C17 109.2(3) . . ? C20 C29 H29A 109.5 . . ? C20 C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? C20 C29 H29C 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? C20 C30 H30A 109.5 . . ? C20 C30 H30B 109.5 . . ? H30A C30 H30B 109.5 . . ? C20 C30 H30C 109.5 . . ? H30A C30 H30C 109.5 . . ? H30B C30 H30C 109.5 . . ? C28 O19 C19 108.3(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 C10 C1 C2 C3 -27.5(4) . . . . ? C1 C2 C3 C5 16.0(4) . . . . ? C1 C2 C3 C4 -165.1(3) . . . . ? C5 C3 C4 C24 -112.8(5) . . . . ? C2 C3 C4 C24 68.4(5) . . . . ? C5 C3 C4 C23 122.3(5) . . . . ? C2 C3 C4 C23 -56.4(5) . . . . ? C4 C3 C5 C6 3.0(7) . . . . ? C2 C3 C5 C6 -178.1(4) . . . . ? C4 C3 C5 C10 -176.4(3) . . . . ? C2 C3 C5 C10 2.4(4) . . . . ? C3 C5 C6 C7 132.3(4) . . . . ? C10 C5 C6 C7 -48.3(4) . . . . ? C5 C6 C7 C8 56.0(4) . . . . ? C6 C7 C8 C26 63.8(4) . . . . ? C6 C7 C8 C9 -56.6(4) . . . . ? C6 C7 C8 C14 -175.4(3) . . . . ? C7 C8 C9 C11 -176.5(3) . . . . ? C26 C8 C9 C11 65.4(4) . . . . ? C14 C8 C9 C11 -56.4(3) . . . . ? C7 C8 C9 C10 51.1(4) . . . . ? C26 C8 C9 C10 -67.0(4) . . . . ? C14 C8 C9 C10 171.2(3) . . . . ? C3 C5 C10 C1 -19.7(4) . . . . ? C6 C5 C10 C1 160.8(3) . . . . ? C3 C5 C10 C25 93.6(4) . . . . ? C6 C5 C10 C25 -85.9(4) . . . . ? C3 C5 C10 C9 -138.2(3) . . . . ? C6 C5 C10 C9 42.3(4) . . . . ? C2 C1 C10 C5 28.3(3) . . . . ? C2 C1 C10 C25 -86.3(3) . . . . ? C2 C1 C10 C9 146.5(3) . . . . ? C11 C9 C10 C5 -175.7(3) . . . . ? C8 C9 C10 C5 -44.1(4) . . . . ? C11 C9 C10 C1 72.3(4) . . . . ? C8 C9 C10 C1 -156.0(3) . . . . ? C11 C9 C10 C25 -50.7(4) . . . . ? C8 C9 C10 C25 80.9(4) . . . . ? C10 C9 C11 C12 -169.5(3) . . . . ? C8 C9 C11 C12 56.6(4) . . . . ? C9 C11 C12 C13 -56.0(4) . . . . ? C11 C12 C13 C18 -176.6(3) . . . . ? C11 C12 C13 C14 56.6(4) . . . . ? C18 C13 C14 C27 -59.7(3) . . . . ? C12 C13 C14 C27 66.2(3) . . . . ? C18 C13 C14 C15 56.2(3) . . . . ? C12 C13 C14 C15 -177.9(3) . . . . ? C18 C13 C14 C8 177.3(2) . . . . ? C12 C13 C14 C8 -56.8(3) . . . . ? C7 C8 C14 C27 51.5(3) . . . . ? C26 C8 C14 C27 171.1(3) . . . . ? C9 C8 C14 C27 -66.3(3) . . . . ? C7 C8 C14 C15 -67.8(3) . . . . ? C26 C8 C14 C15 51.7(3) . . . . ? C9 C8 C14 C15 174.4(3) . . . . ? C7 C8 C14 C13 173.8(2) . . . . ? C26 C8 C14 C13 -66.6(3) . . . . ? C9 C8 C14 C13 56.0(3) . . . . ? C27 C14 C15 C16 58.4(4) . . . . ? C13 C14 C15 C16 -59.5(4) . . . . ? C8 C14 C15 C16 -179.8(3) . . . . ? C14 C15 C16 C17 54.6(4) . . . . ? C15 C16 C17 C28 70.6(4) . . . . ? C15 C16 C17 C18 -44.3(4) . . . . ? C15 C16 C17 C22 -169.0(3) . . . . ? C12 C13 C18 C19 73.2(3) . . . . ? C14 C13 C18 C19 -160.8(3) . . . . ? C12 C13 C18 C17 -175.4(3) . . . . ? C14 C13 C18 C17 -49.5(3) . . . . ? C28 C17 C18 C13 -79.2(3) . . . . ? C16 C17 C18 C13 42.5(4) . . . . ? C22 C17 C18 C13 169.2(3) . . . . ? C28 C17 C18 C19 41.4(3) . . . . ? C16 C17 C18 C19 163.0(3) . . . . ? C22 C17 C18 C19 -70.2(3) . . . . ? C13 C18 C19 O19 77.2(3) . . . . ? C17 C18 C19 O19 -43.9(3) . . . . ? C13 C18 C19 C20 -166.0(3) . . . . ? C17 C18 C19 C20 72.9(3) . . . . ? O19 C19 C20 C29 -65.5(4) . . . . ? C18 C19 C20 C29 -178.9(3) . . . . ? O19 C19 C20 C21 53.7(4) . . . . ? C18 C19 C20 C21 -59.7(4) . . . . ? O19 C19 C20 C30 175.0(3) . . . . ? C18 C19 C20 C30 61.6(4) . . . . ? C29 C20 C21 C22 160.1(3) . . . . ? C30 C20 C21 C22 -78.8(4) . . . . ? C19 C20 C21 C22 41.3(4) . . . . ? C20 C21 C22 C17 -44.9(4) . . . . ? C28 C17 C22 C21 -46.0(4) . . . . ? C16 C17 C22 C21 -170.1(3) . . . . ? C18 C17 C22 C21 61.8(4) . . . . ? C16 C17 C28 O28 33.4(5) . . . . ? C18 C17 C28 O28 156.3(4) . . . . ? C22 C17 C28 O28 -90.5(5) . . . . ? C16 C17 C28 O19 -148.6(3) . . . . ? C18 C17 C28 O19 -25.6(3) . . . . ? C22 C17 C28 O19 87.5(3) . . . . ? O28 C28 O19 C19 175.4(3) . . . . ? C17 C28 O19 C19 -2.8(4) . . . . ? C18 C19 O19 C28 30.4(3) . . . . ? C20 C19 O19 C28 -90.7(3) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.76 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.139 _refine_diff_density_min -0.160 _refine_diff_density_rms 0.035