Supplementary Material (ESI) for Organic & Biomolecular Chemistry This journal is (c) The Royal Society of Chemistry 2007 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_Cambridge 0177 _audit_creation_date 'Mon Apr 03 10:55:24 2006' _audit_creation_method 'by SHELXL-97' _audit_update_record ? _publ_contact_author_name 'Takuji Hirose' _publ_contact_author_address ; Department of Applied Chemistry, Saitama University, Shimo-ohkubo 255, Sakura, Saitama, Saitama 338-8570, Japan ; _publ_contact_author_email hirose@apc.saitama-u.ac.jp _publ_contact_author_fax +81-48-855-3522 _publ_contact_author_phone +81-48-855-3522 _publ_requested_category 'FO or CO' _publ_section_exptl_refinement ; Solvent control of optical resolution of 2-amino-1-phenylethanol using dehydroabietic acid ; loop_ _publ_author_name 'Takuji Hirose' 'Marie Aruga' 'Kayoko Taniguchi' 'Mikio Yasutake' #------------------------------------------------------------------------------ data_R-APE/DAA _database_code_depnum_ccdc_archive 'CCDC 655808' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ' C20 H27 O2, C8 H12 N O, C2 H6 O' _chemical_formula_sum 'C30 H45 N O4' _chemical_formula_weight 483.67 _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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21 _symmetry_space_group_name_Hall P2yb loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 12.595(3) _cell_length_b 6.1165(12) _cell_length_c 18.862(4) _cell_angle_alpha 90.00 _cell_angle_beta 106.42(3) _cell_angle_gamma 90.00 _cell_volume 1393.8(5) _cell_formula_units_Z 2 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.07 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.152 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 528 _exptl_absorpt_coefficient_mu 0.075 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9692 _exptl_absorpt_correction_T_max 0.9970 _exptl_absorpt_process_details '(SADABS; Sheldrick 1996)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 123(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Smart Apex CCD diffractometer' _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 7017 _diffrn_reflns_av_R_equivalents 0.0691 _diffrn_reflns_av_sigmaI/netI 0.0954 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.13 _diffrn_reflns_theta_max 27.49 _reflns_number_total 3349 _reflns_number_gt 2396 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2000)' _computing_cell_refinement SMART _computing_data_reduction 'SAINT (Bruker, 2000)' _computing_structure_solution SHELS-97 _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics Ortep3 _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1000P)^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 'see text' _refine_ls_abs_structure_Flack ? _refine_ls_number_reflns 3349 _refine_ls_number_parameters 324 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1077 _refine_ls_R_factor_gt 0.0672 _refine_ls_wR_factor_ref 0.1885 _refine_ls_wR_factor_gt 0.1642 _refine_ls_goodness_of_fit_ref 1.106 _refine_ls_restrained_S_all 1.106 _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 0.4320(4) -0.2442(8) 0.7055(2) 0.0177(10) Uani 1 1 d . . . C2 C 0.3246(3) -0.1616(9) 0.7198(2) 0.0205(10) Uani 1 1 d . . . H1 H 0.3149 -0.0049 0.7064 0.025 Uiso 1 1 calc R . . H2 H 0.2611 -0.2422 0.6873 0.025 Uiso 1 1 calc R . . C3 C 0.3234(4) -0.1894(9) 0.8003(2) 0.0252(11) Uani 1 1 d . . . H3 H 0.3246 -0.3472 0.8122 0.030 Uiso 1 1 calc R . . H4 H 0.2540 -0.1269 0.8064 0.030 Uiso 1 1 calc R . . C4 C 0.4226(4) -0.0768(8) 0.8541(2) 0.0213(10) Uani 1 1 d . . . H5 H 0.4193 -0.1010 0.9053 0.026 Uiso 1 1 calc R . . H6 H 0.4179 0.0827 0.8446 0.026 Uiso 1 1 calc R . . C5 C 0.5342(4) -0.1621(8) 0.8468(2) 0.0188(10) Uani 1 1 d . . . C6 C 0.6306(4) -0.0234(8) 0.8933(2) 0.0190(10) Uani 1 1 d . . . C7 C 0.6333(4) 0.0341(9) 0.9657(2) 0.0243(11) Uani 1 1 d . . . H7 H 0.5741 -0.0102 0.9844 0.029 Uiso 1 1 calc R . . C8 C 0.7193(4) 0.1532(9) 1.0105(2) 0.0263(12) Uani 1 1 d . . . H8 H 0.7183 0.1891 1.0593 0.032 Uiso 1 1 calc R . . C9 C 0.8080(4) 0.2219(9) 0.9852(2) 0.0241(11) Uani 1 1 d . . . C10 C 0.8057(4) 0.1626(8) 0.9143(2) 0.0232(11) Uani 1 1 d . . . H9 H 0.8651 0.2072 0.8959 0.028 Uiso 1 1 calc R . . C11 C 0.7198(4) 0.0396(8) 0.8681(2) 0.0205(10) Uani 1 1 d . . . C12 C 0.7276(4) -0.0176(9) 0.7916(2) 0.0253(11) Uani 1 1 d . . . H10 H 0.8034 -0.0701 0.7956 0.030 Uiso 1 1 calc R . . H11 H 0.7150 0.1163 0.7609 0.030 Uiso 1 1 calc R . . C13 C 0.6450(4) -0.1916(8) 0.7530(2) 0.0210(10) Uani 1 1 d . . . H12 H 0.6698 -0.3373 0.7741 0.025 Uiso 1 1 calc R . . H13 H 0.6395 -0.1947 0.6996 0.025 Uiso 1 1 calc R . . C14 C 0.5320(3) -0.1369(8) 0.7639(2) 0.0157(9) Uani 1 1 d . . . H14 H 0.5228 0.0236 0.7540 0.019 Uiso 1 1 calc R . . C15 C 0.4353(3) -0.1544(8) 0.6287(2) 0.0161(9) Uani 1 1 d . . . O1 O 0.4462(3) -0.2862(6) 0.57962(15) 0.0229(8) Uani 1 1 d . . . O2 O 0.4265(3) 0.0464(5) 0.61873(16) 0.0216(7) Uani 1 1 d . . . C16 C 0.4349(4) -0.4935(8) 0.7050(2) 0.0250(11) Uani 1 1 d . . . H15 H 0.4108 -0.5500 0.7465 0.038 Uiso 1 1 calc R . . H16 H 0.5106 -0.5430 0.7096 0.038 Uiso 1 1 calc R . . H17 H 0.3853 -0.5476 0.6584 0.038 Uiso 1 1 calc R . . C17 C 0.5535(4) -0.3957(9) 0.8778(2) 0.0264(11) Uani 1 1 d . . . H18 H 0.6186 -0.4582 0.8666 0.040 Uiso 1 1 calc R . . H19 H 0.4884 -0.4858 0.8550 0.040 Uiso 1 1 calc R . . H20 H 0.5657 -0.3921 0.9314 0.040 Uiso 1 1 calc R . . C18 C 0.9012(4) 0.3568(9) 1.0339(3) 0.0275(11) Uani 1 1 d . . . H21 H 0.9568 0.3822 1.0061 0.033 Uiso 1 1 calc R . . C19 C 0.9598(5) 0.2362(10) 1.1054(3) 0.0381(14) Uani 1 1 d . . . H22 H 0.9065 0.2046 1.1332 0.057 Uiso 1 1 calc R . . H23 H 1.0195 0.3278 1.1354 0.057 Uiso 1 1 calc R . . H24 H 0.9908 0.0988 1.0933 0.057 Uiso 1 1 calc R . . C20 C 0.8592(5) 0.5788(10) 1.0503(3) 0.0392(14) Uani 1 1 d . . . H25 H 0.8295 0.6591 1.0040 0.059 Uiso 1 1 calc R . . H26 H 0.9204 0.6619 1.0828 0.059 Uiso 1 1 calc R . . H27 H 0.8008 0.5587 1.0748 0.059 Uiso 1 1 calc R . . N1 N 0.5519(3) -0.6618(7) 0.56228(18) 0.0203(8) Uani 1 1 d . . . H28 H 0.5511 -0.6781 0.5142 0.031 Uiso 1 1 calc R . . H29 H 0.5084 -0.5464 0.5664 0.031 Uiso 1 1 calc R . . H30 H 0.5255 -0.7856 0.5781 0.031 Uiso 1 1 calc R . . O3 O 0.7072(3) -0.9921(6) 0.59237(18) 0.0274(8) Uani 1 1 d . . . H31 H 0.7192 -1.0702 0.5588 0.041 Uiso 1 1 calc R . . C21 C 0.6668(4) -0.6217(8) 0.6082(2) 0.0216(10) Uani 1 1 d . . . H32 H 0.6709 -0.6400 0.6610 0.026 Uiso 1 1 calc R . . H33 H 0.6882 -0.4695 0.6008 0.026 Uiso 1 1 calc R . . C22 C 0.7474(4) -0.7799(8) 0.5877(2) 0.0208(10) Uani 1 1 d . . . H34 H 0.7479 -0.7512 0.5356 0.025 Uiso 1 1 calc R . . C23 C 0.8640(4) -0.7428(8) 0.6391(2) 0.0217(10) Uani 1 1 d . . . C24 C 0.9205(4) -0.9110(10) 0.6840(2) 0.0274(11) Uani 1 1 d . . . H35 H 0.8872 -1.0510 0.6824 0.033 Uiso 1 1 calc R . . C25 C 1.0258(4) -0.8733(11) 0.7312(3) 0.0340(13) Uani 1 1 d . . . H36 H 1.0638 -0.9878 0.7621 0.041 Uiso 1 1 calc R . . C26 C 1.0750(4) -0.6732(12) 0.7334(3) 0.0409(15) Uani 1 1 d . . . H37 H 1.1471 -0.6496 0.7655 0.049 Uiso 1 1 calc R . . C27 C 1.0197(4) -0.5049(10) 0.6890(3) 0.0370(13) Uani 1 1 d . . . H38 H 1.0536 -0.3655 0.6907 0.044 Uiso 1 1 calc R . . C28 C 0.9140(4) -0.5411(9) 0.6419(3) 0.0289(12) Uani 1 1 d . . . H39 H 0.8761 -0.4257 0.6113 0.035 Uiso 1 1 calc R . . O4 O 0.2602(3) 0.2398(6) 0.51420(18) 0.0300(8) Uani 1 1 d . . . H40 H 0.3075 0.1667 0.5455 0.045 Uiso 1 1 calc R . . C29 C 0.1699(5) 0.2924(11) 0.5432(4) 0.0450(16) Uani 1 1 d . . . H41 H 0.1212 0.3993 0.5099 0.054 Uiso 1 1 calc R . . H42 H 0.1995 0.3630 0.5921 0.054 Uiso 1 1 calc R . . C30 C 0.1036(5) 0.1014(13) 0.5515(3) 0.0487(17) Uani 1 1 d . . . H43 H 0.0730 0.0317 0.5032 0.073 Uiso 1 1 calc R . . H44 H 0.0431 0.1484 0.5711 0.073 Uiso 1 1 calc R . . H45 H 0.1507 -0.0032 0.5857 0.073 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 0.019(2) 0.020(3) 0.0138(18) -0.0019(17) 0.0056(16) -0.0023(19) C2 0.015(2) 0.026(3) 0.0206(19) -0.002(2) 0.0051(16) -0.005(2) C3 0.019(2) 0.035(3) 0.024(2) -0.005(2) 0.0096(18) -0.007(2) C4 0.020(2) 0.027(3) 0.0193(19) -0.0044(19) 0.0096(17) -0.002(2) C5 0.021(2) 0.018(2) 0.0164(18) -0.0007(18) 0.0042(16) 0.001(2) C6 0.018(2) 0.020(3) 0.0174(19) -0.0009(18) 0.0035(16) 0.0018(19) C7 0.023(2) 0.033(3) 0.020(2) -0.001(2) 0.0124(17) -0.002(2) C8 0.025(3) 0.034(3) 0.020(2) -0.007(2) 0.0062(18) 0.002(2) C9 0.021(2) 0.029(3) 0.022(2) -0.001(2) 0.0055(18) 0.002(2) C10 0.017(2) 0.031(3) 0.024(2) 0.000(2) 0.0077(17) 0.000(2) C11 0.016(2) 0.027(3) 0.0186(19) 0.0005(19) 0.0053(16) 0.002(2) C12 0.017(2) 0.041(3) 0.018(2) -0.003(2) 0.0061(16) -0.003(2) C13 0.021(2) 0.027(3) 0.0160(18) -0.0028(19) 0.0076(17) 0.002(2) C14 0.020(2) 0.013(2) 0.0145(18) -0.0015(18) 0.0052(16) 0.0013(18) C15 0.009(2) 0.022(3) 0.0183(19) -0.0020(19) 0.0046(15) -0.0001(18) O1 0.0310(18) 0.0217(18) 0.0177(14) 0.0001(14) 0.0097(13) 0.0027(15) O2 0.0274(18) 0.0156(19) 0.0219(15) 0.0010(13) 0.0069(13) 0.0015(14) C16 0.037(3) 0.019(3) 0.020(2) -0.0013(19) 0.0089(19) -0.006(2) C17 0.034(3) 0.022(3) 0.022(2) 0.001(2) 0.0055(19) -0.001(2) C18 0.025(2) 0.032(3) 0.026(2) -0.005(2) 0.0069(19) -0.009(2) C19 0.035(3) 0.040(3) 0.031(2) -0.007(3) -0.004(2) -0.005(3) C20 0.041(3) 0.031(3) 0.041(3) -0.006(3) 0.003(2) -0.011(3) N1 0.025(2) 0.015(2) 0.0216(17) 0.0024(16) 0.0074(15) 0.0018(17) O3 0.0310(19) 0.0179(19) 0.0360(18) -0.0016(15) 0.0141(15) -0.0017(15) C21 0.024(2) 0.019(3) 0.022(2) 0.0000(19) 0.0056(18) -0.001(2) C22 0.027(3) 0.015(2) 0.020(2) -0.0022(19) 0.0077(18) 0.002(2) C23 0.024(2) 0.026(3) 0.0187(19) -0.0009(19) 0.0117(18) 0.005(2) C24 0.027(3) 0.030(3) 0.029(2) 0.004(2) 0.0135(19) 0.008(2) C25 0.033(3) 0.043(4) 0.024(2) 0.006(2) 0.005(2) 0.010(3) C26 0.026(3) 0.058(4) 0.035(3) -0.008(3) 0.001(2) 0.002(3) C27 0.033(3) 0.033(3) 0.043(3) -0.002(3) 0.008(2) -0.007(3) C28 0.031(3) 0.025(3) 0.031(2) 0.001(2) 0.009(2) 0.004(2) O4 0.0246(18) 0.029(2) 0.0348(17) 0.0100(16) 0.0058(14) 0.0043(16) C29 0.026(3) 0.037(4) 0.073(4) -0.005(3) 0.015(3) 0.003(3) C30 0.043(4) 0.072(5) 0.034(3) 0.000(3) 0.015(3) -0.005(4) _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 C16 1.525(7) . ? C1 C2 1.537(6) . ? C1 C15 1.561(6) . ? C1 C14 1.565(6) . ? C2 C3 1.532(6) . ? C2 H1 0.9900 . ? C2 H2 0.9900 . ? C3 C4 1.533(6) . ? C3 H3 0.9900 . ? C3 H4 0.9900 . ? C4 C5 1.541(6) . ? C4 H5 0.9900 . ? C4 H6 0.9900 . ? C5 C17 1.537(7) . ? C5 C6 1.537(6) . ? C5 C14 1.563(5) . ? C6 C11 1.393(6) . ? C6 C7 1.400(6) . ? C7 C8 1.380(7) . ? C7 H7 0.9500 . ? C8 C9 1.398(7) . ? C8 H8 0.9500 . ? C9 C10 1.377(6) . ? C9 C18 1.515(7) . ? C10 C11 1.402(6) . ? C10 H9 0.9500 . ? C11 C12 1.514(6) . ? C12 C13 1.522(7) . ? C12 H10 0.9900 . ? C12 H11 0.9900 . ? C13 C14 1.531(6) . ? C13 H12 0.9900 . ? C13 H13 0.9900 . ? C14 H14 1.0000 . ? C15 O2 1.243(6) . ? C15 O1 1.264(5) . ? C16 H15 0.9800 . ? C16 H16 0.9800 . ? C16 H17 0.9800 . ? C17 H18 0.9800 . ? C17 H19 0.9800 . ? C17 H20 0.9800 . ? C18 C20 1.521(8) . ? C18 C19 1.530(7) . ? C18 H21 1.0000 . ? C19 H22 0.9800 . ? C19 H23 0.9800 . ? C19 H24 0.9800 . ? C20 H25 0.9800 . ? C20 H26 0.9800 . ? C20 H27 0.9800 . ? N1 C21 1.482(6) . ? N1 H28 0.9100 . ? N1 H29 0.9100 . ? N1 H30 0.9100 . ? O3 C22 1.405(6) . ? O3 H31 0.8400 . ? C21 C22 1.529(7) . ? C21 H32 0.9900 . ? C21 H33 0.9900 . ? C22 C23 1.530(6) . ? C22 H34 1.0000 . ? C23 C28 1.380(7) . ? C23 C24 1.393(7) . ? C24 C25 1.392(7) . ? C24 H35 0.9500 . ? C25 C26 1.367(9) . ? C25 H36 0.9500 . ? C26 C27 1.385(9) . ? C26 H37 0.9500 . ? C27 C28 1.394(7) . ? C27 H38 0.9500 . ? C28 H39 0.9500 . ? O4 C29 1.431(7) . ? O4 H40 0.8400 . ? C29 C30 1.470(9) . ? C29 H41 0.9900 . ? C29 H42 0.9900 . ? C30 H43 0.9800 . ? C30 H44 0.9800 . ? C30 H45 0.9800 . ? 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 C16 C1 C2 110.7(4) . . ? C16 C1 C15 109.8(4) . . ? C2 C1 C15 107.6(3) . . ? C16 C1 C14 114.1(4) . . ? C2 C1 C14 108.2(3) . . ? C15 C1 C14 106.2(3) . . ? C3 C2 C1 113.2(4) . . ? C3 C2 H1 108.9 . . ? C1 C2 H1 108.9 . . ? C3 C2 H2 108.9 . . ? C1 C2 H2 108.9 . . ? H1 C2 H2 107.8 . . ? C2 C3 C4 111.8(4) . . ? C2 C3 H3 109.3 . . ? C4 C3 H3 109.3 . . ? C2 C3 H4 109.3 . . ? C4 C3 H4 109.3 . . ? H3 C3 H4 107.9 . . ? C3 C4 C5 112.5(4) . . ? C3 C4 H5 109.1 . . ? C5 C4 H5 109.1 . . ? C3 C4 H6 109.1 . . ? C5 C4 H6 109.1 . . ? H5 C4 H6 107.8 . . ? C17 C5 C4 109.4(4) . . ? C17 C5 C6 106.4(3) . . ? C4 C5 C6 110.8(4) . . ? C17 C5 C14 115.3(4) . . ? C4 C5 C14 107.3(3) . . ? C6 C5 C14 107.7(4) . . ? C11 C6 C7 117.7(4) . . ? C11 C6 C5 122.7(4) . . ? C7 C6 C5 119.5(4) . . ? C8 C7 C6 121.9(4) . . ? C8 C7 H7 119.1 . . ? C6 C7 H7 119.1 . . ? C7 C8 C9 120.9(4) . . ? C7 C8 H8 119.5 . . ? C9 C8 H8 119.5 . . ? C10 C9 C8 116.9(4) . . ? C10 C9 C18 122.2(4) . . ? C8 C9 C18 120.8(4) . . ? C9 C10 C11 123.1(4) . . ? C9 C10 H9 118.4 . . ? C11 C10 H9 118.4 . . ? C6 C11 C10 119.4(4) . . ? C6 C11 C12 122.6(4) . . ? C10 C11 C12 118.1(4) . . ? C11 C12 C13 113.4(4) . . ? C11 C12 H10 108.9 . . ? C13 C12 H10 108.9 . . ? C11 C12 H11 108.9 . . ? C13 C12 H11 108.9 . . ? H10 C12 H11 107.7 . . ? C12 C13 C14 108.5(4) . . ? C12 C13 H12 110.0 . . ? C14 C13 H12 110.0 . . ? C12 C13 H13 110.0 . . ? C14 C13 H13 110.0 . . ? H12 C13 H13 108.4 . . ? C13 C14 C5 111.1(3) . . ? C13 C14 C1 114.0(3) . . ? C5 C14 C1 116.5(4) . . ? C13 C14 H14 104.6 . . ? C5 C14 H14 104.6 . . ? C1 C14 H14 104.6 . . ? O2 C15 O1 122.9(4) . . ? O2 C15 C1 117.6(4) . . ? O1 C15 C1 119.5(4) . . ? C1 C16 H15 109.5 . . ? C1 C16 H16 109.5 . . ? H15 C16 H16 109.5 . . ? C1 C16 H17 109.5 . . ? H15 C16 H17 109.5 . . ? H16 C16 H17 109.5 . . ? C5 C17 H18 109.5 . . ? C5 C17 H19 109.5 . . ? H18 C17 H19 109.5 . . ? C5 C17 H20 109.5 . . ? H18 C17 H20 109.5 . . ? H19 C17 H20 109.5 . . ? C9 C18 C20 110.9(4) . . ? C9 C18 C19 111.7(5) . . ? C20 C18 C19 111.1(4) . . ? C9 C18 H21 107.6 . . ? C20 C18 H21 107.6 . . ? C19 C18 H21 107.6 . . ? C18 C19 H22 109.5 . . ? C18 C19 H23 109.5 . . ? H22 C19 H23 109.5 . . ? C18 C19 H24 109.5 . . ? H22 C19 H24 109.5 . . ? H23 C19 H24 109.5 . . ? C18 C20 H25 109.5 . . ? C18 C20 H26 109.5 . . ? H25 C20 H26 109.5 . . ? C18 C20 H27 109.5 . . ? H25 C20 H27 109.5 . . ? H26 C20 H27 109.5 . . ? C21 N1 H28 109.5 . . ? C21 N1 H29 109.5 . . ? H28 N1 H29 109.5 . . ? C21 N1 H30 109.5 . . ? H28 N1 H30 109.5 . . ? H29 N1 H30 109.5 . . ? C22 O3 H31 109.5 . . ? N1 C21 C22 110.9(4) . . ? N1 C21 H32 109.5 . . ? C22 C21 H32 109.5 . . ? N1 C21 H33 109.5 . . ? C22 C21 H33 109.5 . . ? H32 C21 H33 108.0 . . ? O3 C22 C21 107.0(4) . . ? O3 C22 C23 113.3(4) . . ? C21 C22 C23 109.4(4) . . ? O3 C22 H34 109.0 . . ? C21 C22 H34 109.0 . . ? C23 C22 H34 109.0 . . ? C28 C23 C24 119.2(4) . . ? C28 C23 C22 120.2(4) . . ? C24 C23 C22 120.6(5) . . ? C25 C24 C23 119.8(5) . . ? C25 C24 H35 120.1 . . ? C23 C24 H35 120.1 . . ? C26 C25 C24 120.7(5) . . ? C26 C25 H36 119.7 . . ? C24 C25 H36 119.7 . . ? C25 C26 C27 120.1(5) . . ? C25 C26 H37 120.0 . . ? C27 C26 H37 120.0 . . ? C26 C27 C28 119.6(6) . . ? C26 C27 H38 120.2 . . ? C28 C27 H38 120.2 . . ? C23 C28 C27 120.6(5) . . ? C23 C28 H39 119.7 . . ? C27 C28 H39 119.7 . . ? C29 O4 H40 109.5 . . ? O4 C29 C30 113.5(5) . . ? O4 C29 H41 108.9 . . ? C30 C29 H41 108.9 . . ? O4 C29 H42 108.9 . . ? C30 C29 H42 108.9 . . ? H41 C29 H42 107.7 . . ? C29 C30 H43 109.5 . . ? C29 C30 H44 109.5 . . ? H43 C30 H44 109.5 . . ? C29 C30 H45 109.5 . . ? H43 C30 H45 109.5 . . ? H44 C30 H45 109.5 . . ? 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 C16 C1 C2 C3 74.1(5) . . . . ? C15 C1 C2 C3 -166.0(4) . . . . ? C14 C1 C2 C3 -51.6(5) . . . . ? C1 C2 C3 C4 56.2(6) . . . . ? C2 C3 C4 C5 -57.8(6) . . . . ? C3 C4 C5 C17 -71.2(5) . . . . ? C3 C4 C5 C6 171.9(4) . . . . ? C3 C4 C5 C14 54.6(5) . . . . ? C17 C5 C6 C11 102.8(5) . . . . ? C4 C5 C6 C11 -138.4(4) . . . . ? C14 C5 C6 C11 -21.4(6) . . . . ? C17 C5 C6 C7 -73.8(5) . . . . ? C4 C5 C6 C7 45.0(6) . . . . ? C14 C5 C6 C7 162.0(4) . . . . ? C11 C6 C7 C8 1.4(7) . . . . ? C5 C6 C7 C8 178.2(5) . . . . ? C6 C7 C8 C9 0.1(8) . . . . ? C7 C8 C9 C10 -0.8(8) . . . . ? C7 C8 C9 C18 178.7(5) . . . . ? C8 C9 C10 C11 0.1(8) . . . . ? C18 C9 C10 C11 -179.4(5) . . . . ? C7 C6 C11 C10 -2.1(7) . . . . ? C5 C6 C11 C10 -178.8(4) . . . . ? C7 C6 C11 C12 178.5(5) . . . . ? C5 C6 C11 C12 1.9(7) . . . . ? C9 C10 C11 C6 1.4(7) . . . . ? C9 C10 C11 C12 -179.2(5) . . . . ? C6 C11 C12 C13 -13.6(7) . . . . ? C10 C11 C12 C13 167.0(4) . . . . ? C11 C12 C13 C14 44.7(5) . . . . ? C12 C13 C14 C5 -67.4(5) . . . . ? C12 C13 C14 C1 158.6(4) . . . . ? C17 C5 C14 C13 -64.8(5) . . . . ? C4 C5 C14 C13 173.1(4) . . . . ? C6 C5 C14 C13 53.7(5) . . . . ? C17 C5 C14 C1 68.0(5) . . . . ? C4 C5 C14 C1 -54.1(5) . . . . ? C6 C5 C14 C1 -173.5(4) . . . . ? C16 C1 C14 C13 60.5(5) . . . . ? C2 C1 C14 C13 -175.8(4) . . . . ? C15 C1 C14 C13 -60.5(5) . . . . ? C16 C1 C14 C5 -70.9(5) . . . . ? C2 C1 C14 C5 52.8(5) . . . . ? C15 C1 C14 C5 168.0(4) . . . . ? C16 C1 C15 O2 175.6(4) . . . . ? C2 C1 C15 O2 55.0(5) . . . . ? C14 C1 C15 O2 -60.6(5) . . . . ? C16 C1 C15 O1 -4.1(6) . . . . ? C2 C1 C15 O1 -124.7(4) . . . . ? C14 C1 C15 O1 119.7(4) . . . . ? C10 C9 C18 C20 114.6(5) . . . . ? C8 C9 C18 C20 -64.9(6) . . . . ? C10 C9 C18 C19 -120.9(5) . . . . ? C8 C9 C18 C19 59.7(6) . . . . ? N1 C21 C22 O3 -53.6(5) . . . . ? N1 C21 C22 C23 -176.7(4) . . . . ? O3 C22 C23 C28 -178.8(4) . . . . ? C21 C22 C23 C28 -59.5(5) . . . . ? O3 C22 C23 C24 0.7(6) . . . . ? C21 C22 C23 C24 120.0(5) . . . . ? C28 C23 C24 C25 0.5(7) . . . . ? C22 C23 C24 C25 -179.1(4) . . . . ? C23 C24 C25 C26 -0.7(8) . . . . ? C24 C25 C26 C27 0.6(9) . . . . ? C25 C26 C27 C28 -0.3(9) . . . . ? C24 C23 C28 C27 -0.2(7) . . . . ? C22 C23 C28 C27 179.4(5) . . . . ? C26 C27 C28 C23 0.1(8) . . . . ? _diffrn_measured_fraction_theta_max 0.959 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.959 _refine_diff_density_max 0.340 _refine_diff_density_min -0.286 _refine_diff_density_rms 0.072 # Attachment 'S-APEDAA.CIF' data_S-APE/DAA _database_code_depnum_ccdc_archive 'CCDC 655809' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ' C20 H27 O2, C8 H12 N O' _chemical_formula_sum 'C28 H39 N O3' _chemical_formula_weight 437.60 _chemical_absolute_configuration rm 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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21 _symmetry_space_group_name_Hall P2yb loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 10.981(2) _cell_length_b 6.1913(12) _cell_length_c 17.850(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.37(3) _cell_angle_gamma 90.00 _cell_volume 1213.5(4) _cell_formula_units_Z 2 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.198 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 476 _exptl_absorpt_coefficient_mu 0.076 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9686 _exptl_absorpt_correction_T_max 0.9985 _exptl_absorpt_process_details '(SADABS; Sheldrick 1996)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 123(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Smart Apex CCD diffractometer' _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 8383 _diffrn_reflns_av_R_equivalents 0.1181 _diffrn_reflns_av_sigmaI/netI 0.0969 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 1.14 _diffrn_reflns_theta_max 27.50 _reflns_number_total 3042 _reflns_number_gt 2426 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2000)' _computing_cell_refinement SMART _computing_data_reduction 'SAINT (Bruker, 2000)' _computing_structure_solution SHELS-97 _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics Ortep3 _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1000P)^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 'see text' _refine_ls_abs_structure_Flack ? _refine_ls_number_reflns 3042 _refine_ls_number_parameters 295 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0701 _refine_ls_R_factor_gt 0.0536 _refine_ls_wR_factor_ref 0.1531 _refine_ls_wR_factor_gt 0.1332 _refine_ls_goodness_of_fit_ref 0.918 _refine_ls_restrained_S_all 0.918 _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 0.4302(3) 0.6854(5) 0.27208(17) 0.0211(7) Uani 1 1 d . . . C2 C 0.3221(3) 0.5870(6) 0.22979(18) 0.0243(7) Uani 1 1 d . . . H1 H 0.3137 0.4332 0.2440 0.029 Uiso 1 1 calc R . . H2 H 0.2465 0.6627 0.2446 0.029 Uiso 1 1 calc R . . C3 C 0.3368(3) 0.6032(6) 0.14516(17) 0.0258(7) Uani 1 1 d . . . H3 H 0.3397 0.7574 0.1305 0.031 Uiso 1 1 calc R . . H4 H 0.2652 0.5370 0.1202 0.031 Uiso 1 1 calc R . . C4 C 0.4526(3) 0.4904(6) 0.11822(17) 0.0241(7) Uani 1 1 d . . . H5 H 0.4575 0.5036 0.0631 0.029 Uiso 1 1 calc R . . H6 H 0.4475 0.3348 0.1306 0.029 Uiso 1 1 calc R . . C5 C 0.5693(3) 0.5843(5) 0.15348(16) 0.0202(6) Uani 1 1 d . . . C6 C 0.6805(3) 0.4434(5) 0.13533(17) 0.0203(6) Uani 1 1 d . . . C7 C 0.6929(3) 0.3418(6) 0.06566(17) 0.0251(7) Uani 1 1 d . . . H7 H 0.6301 0.3587 0.0293 0.030 Uiso 1 1 calc R . . C8 C 0.7944(3) 0.2166(6) 0.04785(19) 0.0259(7) Uani 1 1 d . . . H8 H 0.7991 0.1515 -0.0002 0.031 Uiso 1 1 calc R . . C9 C 0.8882(3) 0.1854(5) 0.09887(17) 0.0223(7) Uani 1 1 d . . . C10 C 0.8756(3) 0.2883(6) 0.16738(18) 0.0230(7) Uani 1 1 d . . . H9 H 0.9382 0.2696 0.2037 0.028 Uiso 1 1 calc R . . C11 C 0.7756(3) 0.4185(5) 0.18621(17) 0.0208(6) Uani 1 1 d . . . C12 C 0.7764(3) 0.5299(6) 0.26158(17) 0.0242(7) Uani 1 1 d . . . H10 H 0.8515 0.6176 0.2656 0.029 Uiso 1 1 calc R . . H11 H 0.7803 0.4180 0.3011 0.029 Uiso 1 1 calc R . . C13 C 0.6672(3) 0.6762(5) 0.27709(17) 0.0224(7) Uani 1 1 d . . . H12 H 0.6549 0.6881 0.3318 0.027 Uiso 1 1 calc R . . H13 H 0.6835 0.8227 0.2573 0.027 Uiso 1 1 calc R . . C14 C 0.5523(3) 0.5854(5) 0.24036(16) 0.0189(6) Uani 1 1 d . . . H14 H 0.5503 0.4297 0.2552 0.023 Uiso 1 1 calc R . . C15 C 0.4217(3) 0.6115(5) 0.35515(17) 0.0210(6) Uani 1 1 d . . . O1 O 0.3797(2) 0.4268(4) 0.36893(12) 0.0241(5) Uani 1 1 d . . . O2 O 0.4588(2) 0.7381(4) 0.40552(13) 0.0272(6) Uani 1 1 d . . . C16 C 0.4256(3) 0.9340(5) 0.26845(19) 0.0264(7) Uani 1 1 d . . . H15 H 0.4094 0.9797 0.2168 0.040 Uiso 1 1 calc R . . H16 H 0.5039 0.9934 0.2853 0.040 Uiso 1 1 calc R . . H17 H 0.3606 0.9870 0.3010 0.040 Uiso 1 1 calc R . . C17 C 0.5947(3) 0.8075(6) 0.11806(18) 0.0255(7) Uani 1 1 d . . . H18 H 0.6689 0.8689 0.1402 0.038 Uiso 1 1 calc R . . H19 H 0.5259 0.9042 0.1276 0.038 Uiso 1 1 calc R . . H20 H 0.6054 0.7910 0.0639 0.038 Uiso 1 1 calc R . . C18 C 0.9957(3) 0.0413(5) 0.0803(2) 0.0264(7) Uani 1 1 d . . . H21 H 0.9923 0.0106 0.0254 0.032 Uiso 1 1 calc R . . C19 C 1.1173(3) 0.1466(7) 0.0970(2) 0.0367(9) Uani 1 1 d . . . H22 H 1.1224 0.2847 0.0704 0.055 Uiso 1 1 calc R . . H23 H 1.1832 0.0515 0.0803 0.055 Uiso 1 1 calc R . . H24 H 1.1252 0.1716 0.1510 0.055 Uiso 1 1 calc R . . C20 C 0.9838(4) -0.1742(6) 0.1214(2) 0.0409(9) Uani 1 1 d . . . H25 H 0.9849 -0.1490 0.1756 0.061 Uiso 1 1 calc R . . H26 H 1.0520 -0.2683 0.1078 0.061 Uiso 1 1 calc R . . H27 H 0.9069 -0.2436 0.1070 0.061 Uiso 1 1 calc R . . C21 C 0.8771(3) 0.1328(6) 0.42988(17) 0.0239(7) Uani 1 1 d . . . C22 C 0.9374(3) 0.3299(6) 0.43286(19) 0.0298(8) Uani 1 1 d . . . H28 H 0.9042 0.4457 0.4610 0.036 Uiso 1 1 calc R . . C23 C 1.0472(3) 0.3585(7) 0.3944(2) 0.0345(9) Uani 1 1 d . . . H29 H 1.0878 0.4938 0.3967 0.041 Uiso 1 1 calc R . . C24 C 1.0972(3) 0.1910(7) 0.3529(2) 0.0375(9) Uani 1 1 d . . . H30 H 1.1715 0.2112 0.3269 0.045 Uiso 1 1 calc R . . C25 C 1.0373(4) -0.0059(7) 0.3499(2) 0.0362(9) Uani 1 1 d . . . H31 H 1.0708 -0.1216 0.3218 0.043 Uiso 1 1 calc R . . C26 C 0.9271(3) -0.0352(6) 0.38824(19) 0.0295(8) Uani 1 1 d . . . H32 H 0.8864 -0.1704 0.3857 0.035 Uiso 1 1 calc R . . C27 C 0.7535(3) 0.1078(6) 0.46768(18) 0.0254(7) Uani 1 1 d . . . H33 H 0.7537 0.1924 0.5154 0.030 Uiso 1 1 calc R . . O3 O 0.7247(2) -0.1104(4) 0.48377(13) 0.0299(6) Uani 1 1 d . . . H34 H 0.7082 -0.1227 0.5294 0.045 Uiso 1 1 calc R . . C28 C 0.6570(3) 0.1984(6) 0.41566(18) 0.0249(7) Uani 1 1 d . . . H35 H 0.6672 0.3568 0.4119 0.030 Uiso 1 1 calc R . . H36 H 0.6676 0.1363 0.3650 0.030 Uiso 1 1 calc R . . N1 N 0.5312(2) 0.1486(5) 0.44288(15) 0.0228(6) Uani 1 1 d . . . H37 H 0.5112 0.0106 0.4303 0.034 Uiso 1 1 calc R . . H38 H 0.4771 0.2415 0.4213 0.034 Uiso 1 1 calc R . . H39 H 0.5288 0.1636 0.4936 0.034 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 0.0193(14) 0.0198(16) 0.0244(15) 0.0028(13) 0.0053(12) 0.0012(13) C2 0.0179(14) 0.0234(16) 0.0316(16) 0.0007(14) 0.0035(12) 0.0016(14) C3 0.0238(16) 0.0269(17) 0.0268(15) -0.0012(14) 0.0018(13) 0.0013(15) C4 0.0230(16) 0.0256(17) 0.0236(15) -0.0009(13) 0.0031(13) 0.0018(14) C5 0.0229(15) 0.0167(15) 0.0211(14) 0.0004(12) 0.0061(12) -0.0017(13) C6 0.0202(14) 0.0150(15) 0.0256(15) 0.0044(12) 0.0058(12) -0.0018(13) C7 0.0253(16) 0.0261(17) 0.0239(15) -0.0002(14) 0.0039(13) -0.0002(14) C8 0.0252(16) 0.0273(18) 0.0252(15) -0.0037(14) 0.0074(13) -0.0015(14) C9 0.0221(15) 0.0170(15) 0.0278(16) 0.0010(13) 0.0086(12) -0.0018(13) C10 0.0201(15) 0.0236(17) 0.0254(15) 0.0023(13) 0.0032(12) -0.0010(14) C11 0.0188(13) 0.0185(15) 0.0251(14) 0.0017(13) 0.0069(11) -0.0023(13) C12 0.0165(15) 0.0305(18) 0.0258(15) -0.0012(14) 0.0056(12) -0.0008(14) C13 0.0232(15) 0.0217(16) 0.0225(15) -0.0046(13) 0.0080(12) -0.0038(14) C14 0.0189(14) 0.0168(14) 0.0211(14) 0.0013(12) 0.0059(11) 0.0010(12) C15 0.0175(14) 0.0190(16) 0.0265(15) -0.0012(13) 0.0066(12) 0.0041(12) O1 0.0273(12) 0.0181(11) 0.0268(11) 0.0018(9) 0.0059(9) 0.0012(10) O2 0.0299(13) 0.0244(13) 0.0275(12) -0.0006(10) 0.0057(10) -0.0061(10) C16 0.0296(17) 0.0221(17) 0.0277(16) 0.0030(13) 0.0058(13) 0.0047(15) C17 0.0273(16) 0.0239(17) 0.0256(16) 0.0059(13) 0.0082(13) -0.0006(15) C18 0.0264(17) 0.0199(16) 0.0330(17) -0.0012(14) 0.0094(14) 0.0007(14) C19 0.0250(17) 0.033(2) 0.052(2) -0.0070(18) 0.0066(16) -0.0003(16) C20 0.037(2) 0.0267(19) 0.059(2) 0.0040(19) 0.0203(18) 0.0047(17) C21 0.0207(15) 0.0295(19) 0.0217(15) 0.0021(14) 0.0048(12) -0.0012(14) C22 0.0267(17) 0.0306(18) 0.0321(17) 0.0006(16) 0.0011(14) -0.0015(16) C23 0.0257(17) 0.039(2) 0.0392(19) 0.0088(17) -0.0013(15) -0.0092(16) C24 0.0219(16) 0.052(3) 0.038(2) 0.0098(19) 0.0077(15) -0.0011(18) C25 0.0307(19) 0.043(2) 0.0347(18) -0.0028(18) 0.0140(16) 0.0010(17) C26 0.0277(17) 0.0275(19) 0.0333(17) 0.0004(15) 0.0069(14) -0.0025(15) C27 0.0228(16) 0.0271(17) 0.0263(15) 0.0018(14) 0.0071(12) -0.0003(14) O3 0.0259(12) 0.0313(14) 0.0327(12) 0.0078(11) 0.0097(10) -0.0002(11) C28 0.0196(15) 0.0267(17) 0.0285(16) 0.0024(14) 0.0075(13) -0.0035(14) N1 0.0209(13) 0.0201(14) 0.0274(13) 0.0011(11) 0.0047(11) -0.0003(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 1.530(5) . ? C1 C16 1.541(5) . ? C1 C15 1.555(4) . ? C1 C14 1.585(4) . ? C2 C3 1.524(5) . ? C2 H1 0.9900 . ? C2 H2 0.9900 . ? C3 C4 1.531(5) . ? C3 H3 0.9900 . ? C3 H4 0.9900 . ? C4 C5 1.538(4) . ? C4 H5 0.9900 . ? C4 H6 0.9900 . ? C5 C6 1.537(4) . ? C5 C17 1.546(5) . ? C5 C14 1.563(4) . ? C6 C11 1.388(4) . ? C6 C7 1.401(4) . ? C7 C8 1.396(5) . ? C7 H7 0.9500 . ? C8 C9 1.385(5) . ? C8 H8 0.9500 . ? C9 C10 1.387(5) . ? C9 C18 1.517(5) . ? C10 C11 1.404(5) . ? C10 H9 0.9500 . ? C11 C12 1.512(4) . ? C12 C13 1.529(4) . ? C12 H10 0.9900 . ? C12 H11 0.9900 . ? C13 C14 1.525(4) . ? C13 H12 0.9900 . ? C13 H13 0.9900 . ? C14 H14 1.0000 . ? C15 O1 1.258(4) . ? C15 O2 1.258(4) . ? C16 H15 0.9800 . ? C16 H16 0.9800 . ? C16 H17 0.9800 . ? C17 H18 0.9800 . ? C17 H19 0.9800 . ? C17 H20 0.9800 . ? C18 C19 1.514(5) . ? C18 C20 1.528(5) . ? C18 H21 1.0000 . ? C19 H22 0.9800 . ? C19 H23 0.9800 . ? C19 H24 0.9800 . ? C20 H25 0.9800 . ? C20 H26 0.9800 . ? C20 H27 0.9800 . ? C21 C22 1.389(5) . ? C21 C26 1.393(5) . ? C21 C27 1.527(4) . ? C22 C23 1.402(5) . ? C22 H28 0.9500 . ? C23 C24 1.390(6) . ? C23 H29 0.9500 . ? C24 C25 1.386(6) . ? C24 H30 0.9500 . ? C25 C26 1.405(5) . ? C25 H31 0.9500 . ? C26 H32 0.9500 . ? C27 O3 1.417(4) . ? C27 C28 1.513(5) . ? C27 H33 1.0000 . ? O3 H34 0.8400 . ? C28 N1 1.500(4) . ? C28 H35 0.9900 . ? C28 H36 0.9900 . ? N1 H37 0.9100 . ? N1 H38 0.9100 . ? N1 H39 0.9100 . ? 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 C16 110.6(3) . . ? C2 C1 C15 107.6(3) . . ? C16 C1 C15 109.4(3) . . ? C2 C1 C14 108.9(3) . . ? C16 C1 C14 113.7(3) . . ? C15 C1 C14 106.4(2) . . ? C3 C2 C1 112.1(3) . . ? C3 C2 H1 109.2 . . ? C1 C2 H1 109.2 . . ? C3 C2 H2 109.2 . . ? C1 C2 H2 109.2 . . ? H1 C2 H2 107.9 . . ? C2 C3 C4 112.0(3) . . ? C2 C3 H3 109.2 . . ? C4 C3 H3 109.2 . . ? C2 C3 H4 109.2 . . ? C4 C3 H4 109.2 . . ? H3 C3 H4 107.9 . . ? C3 C4 C5 113.0(3) . . ? C3 C4 H5 109.0 . . ? C5 C4 H5 109.0 . . ? C3 C4 H6 109.0 . . ? C5 C4 H6 109.0 . . ? H5 C4 H6 107.8 . . ? C4 C5 C6 111.1(3) . . ? C4 C5 C17 108.8(3) . . ? C6 C5 C17 106.0(2) . . ? C4 C5 C14 107.7(2) . . ? C6 C5 C14 108.1(2) . . ? C17 C5 C14 115.1(3) . . ? C11 C6 C7 117.0(3) . . ? C11 C6 C5 121.4(3) . . ? C7 C6 C5 121.6(3) . . ? C8 C7 C6 122.3(3) . . ? C8 C7 H7 118.9 . . ? C6 C7 H7 118.9 . . ? C9 C8 C7 121.3(3) . . ? C9 C8 H8 119.3 . . ? C7 C8 H8 119.3 . . ? C8 C9 C10 115.9(3) . . ? C8 C9 C18 121.0(3) . . ? C10 C9 C18 123.0(3) . . ? C9 C10 C11 123.9(3) . . ? C9 C10 H9 118.0 . . ? C11 C10 H9 118.0 . . ? C6 C11 C10 119.5(3) . . ? C6 C11 C12 122.1(3) . . ? C10 C11 C12 118.4(3) . . ? C11 C12 C13 115.6(3) . . ? C11 C12 H10 108.4 . . ? C13 C12 H10 108.4 . . ? C11 C12 H11 108.4 . . ? C13 C12 H11 108.4 . . ? H10 C12 H11 107.5 . . ? C14 C13 C12 110.5(3) . . ? C14 C13 H12 109.5 . . ? C12 C13 H12 109.5 . . ? C14 C13 H13 109.5 . . ? C12 C13 H13 109.5 . . ? H12 C13 H13 108.1 . . ? C13 C14 C5 109.0(2) . . ? C13 C14 C1 113.7(3) . . ? C5 C14 C1 117.5(2) . . ? C13 C14 H14 105.2 . . ? C5 C14 H14 105.2 . . ? C1 C14 H14 105.2 . . ? O1 C15 O2 122.9(3) . . ? O1 C15 C1 118.6(3) . . ? O2 C15 C1 118.5(3) . . ? C1 C16 H15 109.5 . . ? C1 C16 H16 109.5 . . ? H15 C16 H16 109.5 . . ? C1 C16 H17 109.5 . . ? H15 C16 H17 109.5 . . ? H16 C16 H17 109.5 . . ? C5 C17 H18 109.5 . . ? C5 C17 H19 109.5 . . ? H18 C17 H19 109.5 . . ? C5 C17 H20 109.5 . . ? H18 C17 H20 109.5 . . ? H19 C17 H20 109.5 . . ? C19 C18 C9 113.0(3) . . ? C19 C18 C20 111.1(3) . . ? C9 C18 C20 109.9(3) . . ? C19 C18 H21 107.6 . . ? C9 C18 H21 107.6 . . ? C20 C18 H21 107.6 . . ? C18 C19 H22 109.5 . . ? C18 C19 H23 109.5 . . ? H22 C19 H23 109.5 . . ? C18 C19 H24 109.5 . . ? H22 C19 H24 109.5 . . ? H23 C19 H24 109.5 . . ? C18 C20 H25 109.5 . . ? C18 C20 H26 109.5 . . ? H25 C20 H26 109.5 . . ? C18 C20 H27 109.5 . . ? H25 C20 H27 109.5 . . ? H26 C20 H27 109.5 . . ? C22 C21 C26 119.1(3) . . ? C22 C21 C27 119.8(3) . . ? C26 C21 C27 120.9(3) . . ? C21 C22 C23 120.2(4) . . ? C21 C22 H28 119.9 . . ? C23 C22 H28 119.9 . . ? C24 C23 C22 120.7(4) . . ? C24 C23 H29 119.6 . . ? C22 C23 H29 119.6 . . ? C25 C24 C23 119.2(3) . . ? C25 C24 H30 120.4 . . ? C23 C24 H30 120.4 . . ? C24 C25 C26 120.3(4) . . ? C24 C25 H31 119.8 . . ? C26 C25 H31 119.8 . . ? C21 C26 C25 120.5(4) . . ? C21 C26 H32 119.8 . . ? C25 C26 H32 119.8 . . ? O3 C27 C28 108.8(3) . . ? O3 C27 C21 112.7(3) . . ? C28 C27 C21 108.2(3) . . ? O3 C27 H33 109.0 . . ? C28 C27 H33 109.0 . . ? C21 C27 H33 109.0 . . ? C27 O3 H34 109.5 . . ? N1 C28 C27 111.6(3) . . ? N1 C28 H35 109.3 . . ? C27 C28 H35 109.3 . . ? N1 C28 H36 109.3 . . ? C27 C28 H36 109.3 . . ? H35 C28 H36 108.0 . . ? C28 N1 H37 109.5 . . ? C28 N1 H38 109.5 . . ? H37 N1 H38 109.5 . . ? C28 N1 H39 109.5 . . ? H37 N1 H39 109.5 . . ? H38 N1 H39 109.5 . . ? 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 C16 C1 C2 C3 74.2(4) . . . . ? C15 C1 C2 C3 -166.4(3) . . . . ? C14 C1 C2 C3 -51.5(3) . . . . ? C1 C2 C3 C4 58.5(4) . . . . ? C2 C3 C4 C5 -59.5(4) . . . . ? C3 C4 C5 C6 170.5(3) . . . . ? C3 C4 C5 C17 -73.1(3) . . . . ? C3 C4 C5 C14 52.3(3) . . . . ? C4 C5 C6 C11 -145.9(3) . . . . ? C17 C5 C6 C11 96.0(3) . . . . ? C14 C5 C6 C11 -27.9(4) . . . . ? C4 C5 C6 C7 36.8(4) . . . . ? C17 C5 C6 C7 -81.2(4) . . . . ? C14 C5 C6 C7 154.8(3) . . . . ? C11 C6 C7 C8 1.4(5) . . . . ? C5 C6 C7 C8 178.8(3) . . . . ? C6 C7 C8 C9 0.4(5) . . . . ? C7 C8 C9 C10 -1.0(5) . . . . ? C7 C8 C9 C18 177.4(3) . . . . ? C8 C9 C10 C11 -0.3(5) . . . . ? C18 C9 C10 C11 -178.6(3) . . . . ? C7 C6 C11 C10 -2.6(4) . . . . ? C5 C6 C11 C10 -180.0(3) . . . . ? C7 C6 C11 C12 176.6(3) . . . . ? C5 C6 C11 C12 -0.8(4) . . . . ? C9 C10 C11 C6 2.2(5) . . . . ? C9 C10 C11 C12 -177.1(3) . . . . ? C6 C11 C12 C13 -1.6(4) . . . . ? C10 C11 C12 C13 177.6(3) . . . . ? C11 C12 C13 C14 33.8(4) . . . . ? C12 C13 C14 C5 -63.5(3) . . . . ? C12 C13 C14 C1 163.3(3) . . . . ? C4 C5 C14 C13 179.5(3) . . . . ? C6 C5 C14 C13 59.4(3) . . . . ? C17 C5 C14 C13 -58.9(3) . . . . ? C4 C5 C14 C1 -49.3(4) . . . . ? C6 C5 C14 C1 -169.4(3) . . . . ? C17 C5 C14 C1 72.3(3) . . . . ? C2 C1 C14 C13 178.5(3) . . . . ? C16 C1 C14 C13 54.7(4) . . . . ? C15 C1 C14 C13 -65.8(3) . . . . ? C2 C1 C14 C5 49.5(3) . . . . ? C16 C1 C14 C5 -74.3(4) . . . . ? C15 C1 C14 C5 165.2(3) . . . . ? C2 C1 C15 O1 33.9(4) . . . . ? C16 C1 C15 O1 154.1(3) . . . . ? C14 C1 C15 O1 -82.7(3) . . . . ? C2 C1 C15 O2 -147.0(3) . . . . ? C16 C1 C15 O2 -26.9(4) . . . . ? C14 C1 C15 O2 96.4(3) . . . . ? C8 C9 C18 C19 131.2(4) . . . . ? C10 C9 C18 C19 -50.6(4) . . . . ? C8 C9 C18 C20 -104.1(4) . . . . ? C10 C9 C18 C20 74.1(4) . . . . ? C26 C21 C22 C23 0.0(5) . . . . ? C27 C21 C22 C23 -176.0(3) . . . . ? C21 C22 C23 C24 0.0(5) . . . . ? C22 C23 C24 C25 -0.1(6) . . . . ? C23 C24 C25 C26 0.2(6) . . . . ? C22 C21 C26 C25 0.2(5) . . . . ? C27 C21 C26 C25 176.1(3) . . . . ? C24 C25 C26 C21 -0.3(6) . . . . ? C22 C21 C27 O3 -158.4(3) . . . . ? C26 C21 C27 O3 25.7(4) . . . . ? C22 C21 C27 C28 81.3(4) . . . . ? C26 C21 C27 C28 -94.6(4) . . . . ? O3 C27 C28 N1 48.2(4) . . . . ? C21 C27 C28 N1 170.9(3) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.310 _refine_diff_density_min -0.304 _refine_diff_density_rms 0.062 # Attachment 'S-APE2xDAA.CIF' #------------------------------------------------------------------------------ data_S-APE/2xDAA _database_code_depnum_ccdc_archive 'CCDC 655810' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C20 H28 O2, C20 H27 O2, C8 H12 N O' _chemical_formula_sum 'C48 H67 N O5' _chemical_formula_weight 738.03 _chemical_absolute_configuration ? 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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M P212121 _symmetry_space_group_name_Hall P2ac2ab loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 6.3023(8) _cell_length_b 19.070(2) _cell_length_c 35.095(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 4218.0(9) _cell_formula_units_Z 4 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.162 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1608 _exptl_absorpt_coefficient_mu 0.074 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9712 _exptl_absorpt_correction_T_max 0.9927 _exptl_absorpt_process_details '(SADABS; Sheldrick 1996)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 123(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 Smart Apex CCD diffractometer' _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 29325 _diffrn_reflns_av_R_equivalents 0.2007 _diffrn_reflns_av_sigmaI/netI 0.1396 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -39 _diffrn_reflns_limit_l_max 45 _diffrn_reflns_theta_min 1.16 _diffrn_reflns_theta_max 27.50 _reflns_number_total 5487 _reflns_number_gt 3658 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2000)' _computing_cell_refinement SMART _computing_data_reduction 'SAINT (Bruker, 2000)' _computing_structure_solution SHELS-97 _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics Ortep3 _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1000P)^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 'see text' _refine_ls_abs_structure_Flack ? _refine_ls_number_reflns 5487 _refine_ls_number_parameters 498 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1378 _refine_ls_R_factor_gt 0.0927 _refine_ls_wR_factor_ref 0.2269 _refine_ls_wR_factor_gt 0.1999 _refine_ls_goodness_of_fit_ref 1.148 _refine_ls_restrained_S_all 1.148 _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 N1 N 0.4595(7) 0.7434(2) 0.02559(12) 0.0208(10) Uani 1 1 d . . . H1 H 0.5754 0.7691 0.0323 0.031 Uiso 1 1 calc R . . H2 H 0.3405 0.7699 0.0285 0.031 Uiso 1 1 calc R . . H3 H 0.4715 0.7298 0.0008 0.031 Uiso 1 1 calc R . . C1 C 0.4451(9) 0.6810(3) 0.05013(16) 0.0228(12) Uani 1 1 d . . . H4 H 0.2950 0.6662 0.0521 0.027 Uiso 1 1 calc R . . H5 H 0.4958 0.6929 0.0760 0.027 Uiso 1 1 calc R . . C2 C 0.5763(9) 0.6211(3) 0.03442(17) 0.0267(13) Uani 1 1 d . . . H6 H 0.5194 0.6069 0.0089 0.032 Uiso 1 1 calc R . . O1 O 0.7881(7) 0.64623(19) 0.03018(12) 0.0309(10) Uani 1 1 d . . . H7 H 0.8479 0.6247 0.0123 0.046 Uiso 1 1 calc R . . C3 C 0.5641(11) 0.5590(3) 0.06161(17) 0.0309(14) Uani 1 1 d . . . C4 C 0.3747(11) 0.5210(3) 0.0635(2) 0.0396(17) Uani 1 1 d . . . H8 H 0.2583 0.5323 0.0475 0.047 Uiso 1 1 calc R . . C5 C 0.3615(13) 0.4664(3) 0.0895(2) 0.051(2) Uani 1 1 d . . . H9 H 0.2350 0.4394 0.0906 0.062 Uiso 1 1 calc R . . C6 C 0.5215(15) 0.4506(3) 0.1133(2) 0.054(2) Uani 1 1 d . . . H10 H 0.5058 0.4137 0.1312 0.065 Uiso 1 1 calc R . . C7 C 0.7085(14) 0.4878(3) 0.1115(2) 0.0452(18) Uani 1 1 d . . . H11 H 0.8225 0.4764 0.1281 0.054 Uiso 1 1 calc R . . C8 C 0.7296(12) 0.5424(3) 0.08521(18) 0.0352(16) Uani 1 1 d . . . H12 H 0.8587 0.5679 0.0837 0.042 Uiso 1 1 calc R . . C9 C 0.3330(12) 0.6123(4) 0.1955(2) 0.0408(16) Uani 1 1 d . . . H13 H 0.3516 0.5685 0.1831 0.049 Uiso 1 1 calc R . . C10 C 0.4321(11) 0.6239(4) 0.2298(2) 0.0412(16) Uani 1 1 d . . . C11 C 0.4129(12) 0.6876(4) 0.24640(19) 0.0432(17) Uani 1 1 d . . . H14 H 0.4842 0.6968 0.2697 0.052 Uiso 1 1 calc R . . C12 C 0.2907(10) 0.7394(4) 0.22977(18) 0.0374(15) Uani 1 1 d . . . H15 H 0.2767 0.7832 0.2424 0.045 Uiso 1 1 calc R . . C13 C 0.1877(10) 0.7294(3) 0.19517(17) 0.0294(13) Uani 1 1 d . . . C14 C 0.2041(11) 0.6639(3) 0.17827(17) 0.0352(15) Uani 1 1 d . . . C15 C 0.0951(12) 0.6452(3) 0.14133(17) 0.0343(15) Uani 1 1 d . . . H16 H 0.0268 0.5987 0.1441 0.041 Uiso 1 1 calc R . . H17 H 0.2033 0.6414 0.1210 0.041 Uiso 1 1 calc R . . C16 C -0.0706(10) 0.6981(3) 0.12933(17) 0.0282(13) Uani 1 1 d . . . H18 H -0.2009 0.6916 0.1447 0.034 Uiso 1 1 calc R . . H19 H -0.1073 0.6910 0.1022 0.034 Uiso 1 1 calc R . . C17 C 0.0166(9) 0.7725(3) 0.13521(15) 0.0210(11) Uani 1 1 d . . . H20 H 0.1643 0.7710 0.1248 0.025 Uiso 1 1 calc R . . C18 C 0.0438(9) 0.7877(3) 0.17847(16) 0.0261(13) Uani 1 1 d . . . C19 C 0.1542(10) 0.8600(3) 0.18279(17) 0.0311(14) Uani 1 1 d . . . H21 H 0.1592 0.8729 0.2101 0.037 Uiso 1 1 calc R . . H22 H 0.3021 0.8565 0.1734 0.037 Uiso 1 1 calc R . . C20 C 0.0384(11) 0.9171(3) 0.16070(17) 0.0337(15) Uani 1 1 d . . . H23 H 0.1161 0.9619 0.1637 0.040 Uiso 1 1 calc R . . H24 H -0.1049 0.9234 0.1717 0.040 Uiso 1 1 calc R . . C21 C 0.0166(10) 0.9006(3) 0.11798(16) 0.0267(13) Uani 1 1 d . . . H25 H 0.1594 0.8986 0.1063 0.032 Uiso 1 1 calc R . . H26 H -0.0638 0.9387 0.1054 0.032 Uiso 1 1 calc R . . C22 C -0.0987(9) 0.8299(3) 0.11134(16) 0.0227(12) Uani 1 1 d . . . C23 C 0.5705(13) 0.5670(4) 0.2486(2) 0.053(2) Uani 1 1 d . . . H27 H 0.6058 0.5842 0.2748 0.064 Uiso 1 1 calc R . . C24 C 0.4563(18) 0.4986(5) 0.2533(3) 0.078(3) Uani 1 1 d . . . H28 H 0.4186 0.4800 0.2282 0.117 Uiso 1 1 calc R . . H29 H 0.3269 0.5061 0.2683 0.117 Uiso 1 1 calc R . . H30 H 0.5485 0.4652 0.2666 0.117 Uiso 1 1 calc R . . C25 C 0.7735(16) 0.5580(7) 0.2283(3) 0.098(4) Uani 1 1 d . . . H31 H 0.8582 0.5219 0.2411 0.148 Uiso 1 1 calc R . . H32 H 0.8516 0.6024 0.2284 0.148 Uiso 1 1 calc R . . H33 H 0.7457 0.5436 0.2020 0.148 Uiso 1 1 calc R . . C26 C -0.1657(10) 0.7871(4) 0.20167(16) 0.0328(14) Uani 1 1 d . . . H34 H -0.2498 0.7459 0.1946 0.049 Uiso 1 1 calc R . . H35 H -0.2468 0.8297 0.1961 0.049 Uiso 1 1 calc R . . H36 H -0.1329 0.7854 0.2289 0.049 Uiso 1 1 calc R . . C27 C -0.3365(10) 0.8362(3) 0.12000(17) 0.0318(14) Uani 1 1 d . . . H37 H -0.3991 0.7892 0.1214 0.048 Uiso 1 1 calc R . . H38 H -0.4060 0.8629 0.0997 0.048 Uiso 1 1 calc R . . H39 H -0.3562 0.8603 0.1444 0.048 Uiso 1 1 calc R . . C28 C -0.0644(9) 0.8132(3) 0.06853(16) 0.0217(12) Uani 1 1 d . . . O2 O -0.2066(7) 0.83262(18) 0.04476(11) 0.0266(9) Uani 1 1 d . . . O3 O 0.0977(7) 0.7816(2) 0.05834(11) 0.0317(10) Uani 1 1 d . . . C29 C 0.1517(10) 0.6917(3) 0.34202(16) 0.0244(12) Uani 1 1 d . . . H40 H 0.1138 0.6645 0.3204 0.029 Uiso 1 1 calc R . . C30 C 0.0753(10) 0.7601(3) 0.34460(17) 0.0282(13) Uani 1 1 d . . . C31 C 0.1338(9) 0.7983(3) 0.37718(16) 0.0245(13) Uani 1 1 d . . . H41 H 0.0837 0.8449 0.3804 0.029 Uiso 1 1 calc R . . C32 C 0.2632(9) 0.7690(3) 0.40462(16) 0.0245(13) Uani 1 1 d . . . H42 H 0.3042 0.7966 0.4259 0.029 Uiso 1 1 calc R . . C33 C 0.3358(9) 0.6997(3) 0.40197(16) 0.0227(12) Uani 1 1 d . . . C34 C 0.2806(10) 0.6611(3) 0.36957(16) 0.0254(13) Uani 1 1 d . . . C35 C 0.3513(11) 0.5855(3) 0.36395(16) 0.0288(14) Uani 1 1 d . . . H43 H 0.2270 0.5544 0.3672 0.035 Uiso 1 1 calc R . . H44 H 0.4031 0.5798 0.3375 0.035 Uiso 1 1 calc R . . C36 C 0.5233(11) 0.5627(3) 0.39103(17) 0.0323(14) Uani 1 1 d . . . H45 H 0.6615 0.5820 0.3827 0.039 Uiso 1 1 calc R . . H46 H 0.5338 0.5109 0.3912 0.039 Uiso 1 1 calc R . . C37 C 0.4696(9) 0.5894(3) 0.43127(15) 0.0216(12) Uani 1 1 d . . . H47 H 0.3158 0.5785 0.4350 0.026 Uiso 1 1 calc R . . C38 C 0.4851(9) 0.6714(3) 0.43295(16) 0.0231(12) Uani 1 1 d . . . C39 C 0.4090(10) 0.6930(3) 0.47312(16) 0.0276(13) Uani 1 1 d . . . H48 H 0.4285 0.7442 0.4761 0.033 Uiso 1 1 calc R . . H49 H 0.2553 0.6830 0.4753 0.033 Uiso 1 1 calc R . . C40 C 0.5241(11) 0.6559(3) 0.50527(16) 0.0298(14) Uani 1 1 d . . . H50 H 0.4641 0.6713 0.5300 0.036 Uiso 1 1 calc R . . H51 H 0.6760 0.6692 0.5048 0.036 Uiso 1 1 calc R . . C41 C 0.5046(11) 0.5763(3) 0.50192(16) 0.0286(13) Uani 1 1 d . . . H52 H 0.3540 0.5628 0.5050 0.034 Uiso 1 1 calc R . . H53 H 0.5866 0.5540 0.5227 0.034 Uiso 1 1 calc R . . C42 C 0.5864(9) 0.5490(3) 0.46332(17) 0.0259(13) Uani 1 1 d . . . C43 C -0.0661(11) 0.7911(3) 0.31427(17) 0.0294(14) Uani 1 1 d . . . H54 H -0.0531 0.7609 0.2911 0.035 Uiso 1 1 calc R . . C44 C -0.0011(14) 0.8651(3) 0.3030(2) 0.0457(18) Uani 1 1 d . . . H55 H -0.0277 0.8972 0.3243 0.068 Uiso 1 1 calc R . . H56 H -0.0840 0.8801 0.2808 0.068 Uiso 1 1 calc R . . H57 H 0.1503 0.8658 0.2966 0.068 Uiso 1 1 calc R . . C45 C -0.2964(12) 0.7888(4) 0.3270(2) 0.0482(19) Uani 1 1 d . . . H58 H -0.3359 0.7404 0.3331 0.072 Uiso 1 1 calc R . . H59 H -0.3873 0.8064 0.3064 0.072 Uiso 1 1 calc R . . H60 H -0.3145 0.8183 0.3496 0.072 Uiso 1 1 calc R . . C46 C 0.7073(10) 0.7028(3) 0.42601(19) 0.0332(15) Uani 1 1 d . . . H61 H 0.7712 0.6807 0.4036 0.050 Uiso 1 1 calc R . . H62 H 0.7971 0.6943 0.4483 0.050 Uiso 1 1 calc R . . H63 H 0.6946 0.7534 0.4217 0.050 Uiso 1 1 calc R . . C47 C 0.8286(9) 0.5507(3) 0.46142(19) 0.0337(15) Uani 1 1 d . . . H64 H 0.8869 0.5145 0.4783 0.051 Uiso 1 1 calc R . . H65 H 0.8797 0.5969 0.4695 0.051 Uiso 1 1 calc R . . H66 H 0.8747 0.5417 0.4352 0.051 Uiso 1 1 calc R . . C48 C 0.5153(10) 0.4723(3) 0.46131(16) 0.0260(13) Uani 1 1 d . . . O4 O 0.6410(7) 0.4232(2) 0.46449(13) 0.0384(11) Uani 1 1 d . . . O5 O 0.3130(7) 0.46334(19) 0.45741(14) 0.0339(10) Uani 1 1 d . . . H67 H 0.2847 0.4203 0.4583 0.051 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 N1 0.018(2) 0.017(2) 0.027(2) 0.0016(19) 0.0030(19) 0.0031(18) C1 0.024(3) 0.014(2) 0.031(3) 0.001(2) -0.001(2) -0.002(2) C2 0.022(3) 0.024(3) 0.035(3) -0.002(3) -0.004(3) 0.000(2) O1 0.031(2) 0.0171(19) 0.045(3) -0.0009(18) 0.001(2) 0.0034(17) C3 0.045(4) 0.017(3) 0.031(3) -0.004(2) -0.003(3) 0.005(3) C4 0.039(4) 0.021(3) 0.059(5) 0.003(3) -0.006(3) -0.006(3) C5 0.053(5) 0.022(3) 0.079(6) 0.006(3) 0.013(4) -0.009(3) C6 0.074(6) 0.019(3) 0.069(5) 0.013(3) -0.001(5) -0.005(4) C7 0.068(5) 0.017(3) 0.051(4) 0.003(3) -0.012(4) 0.006(3) C8 0.050(4) 0.011(3) 0.044(4) 0.001(3) -0.005(3) 0.001(3) C9 0.043(4) 0.034(3) 0.045(4) 0.009(3) 0.002(3) 0.004(3) C10 0.034(4) 0.048(4) 0.041(4) 0.014(3) -0.007(3) -0.001(3) C11 0.043(4) 0.057(4) 0.030(4) 0.012(3) -0.010(3) -0.007(4) C12 0.032(3) 0.050(4) 0.030(3) 0.003(3) 0.001(3) 0.002(3) C13 0.029(3) 0.032(3) 0.028(3) 0.006(3) 0.007(3) 0.002(3) C14 0.042(4) 0.034(3) 0.029(3) 0.007(3) 0.003(3) 0.002(3) C15 0.054(4) 0.020(3) 0.029(3) 0.004(2) -0.010(3) -0.003(3) C16 0.026(3) 0.027(3) 0.032(3) 0.003(2) -0.006(3) -0.014(3) C17 0.019(3) 0.018(3) 0.026(3) 0.000(2) -0.002(2) -0.003(2) C18 0.027(3) 0.026(3) 0.025(3) -0.001(2) 0.002(2) 0.000(3) C19 0.033(3) 0.029(3) 0.032(3) -0.006(3) -0.002(3) -0.005(3) C20 0.043(4) 0.020(3) 0.038(3) -0.005(3) 0.002(3) -0.004(3) C21 0.031(3) 0.016(3) 0.033(3) 0.000(2) 0.007(3) -0.004(2) C22 0.022(3) 0.017(2) 0.030(3) -0.001(2) 0.002(2) 0.000(2) C23 0.048(5) 0.046(4) 0.065(5) 0.019(4) -0.009(4) 0.001(4) C24 0.084(7) 0.055(5) 0.096(7) 0.031(5) -0.026(6) -0.002(5) C25 0.058(6) 0.125(10) 0.112(9) 0.053(8) 0.023(6) 0.041(7) C26 0.027(3) 0.048(4) 0.024(3) 0.001(3) 0.003(3) -0.002(3) C27 0.032(3) 0.036(3) 0.027(3) -0.002(3) 0.004(3) 0.003(3) C28 0.029(3) 0.009(2) 0.027(3) 0.001(2) 0.009(3) -0.004(2) O2 0.042(2) 0.0114(17) 0.027(2) -0.0018(16) 0.002(2) 0.0015(18) O3 0.035(2) 0.0239(19) 0.036(2) 0.0025(18) 0.0102(19) 0.0066(19) C29 0.033(3) 0.017(2) 0.024(3) -0.004(2) 0.002(3) -0.006(2) C30 0.032(3) 0.024(3) 0.028(3) 0.003(2) 0.004(3) 0.003(3) C31 0.027(3) 0.019(3) 0.028(3) -0.002(2) 0.001(2) 0.000(2) C32 0.031(3) 0.016(2) 0.027(3) -0.005(2) -0.003(2) -0.002(2) C33 0.028(3) 0.012(2) 0.028(3) 0.003(2) 0.002(2) 0.001(2) C34 0.037(3) 0.017(3) 0.022(3) -0.001(2) 0.006(3) -0.001(3) C35 0.043(4) 0.015(3) 0.028(3) -0.004(2) 0.001(3) 0.003(3) C36 0.045(4) 0.016(3) 0.036(3) -0.003(2) 0.009(3) 0.003(3) C37 0.027(3) 0.013(2) 0.025(3) -0.001(2) 0.004(2) -0.001(2) C38 0.020(3) 0.012(2) 0.036(3) -0.002(2) -0.002(3) -0.001(2) C39 0.036(3) 0.018(2) 0.029(3) -0.001(2) -0.001(3) 0.002(2) C40 0.043(4) 0.020(3) 0.027(3) -0.006(2) -0.002(3) 0.009(3) C41 0.040(3) 0.019(3) 0.027(3) 0.000(2) -0.008(3) 0.007(3) C42 0.021(3) 0.021(3) 0.036(3) -0.002(2) -0.002(3) 0.005(2) C43 0.041(4) 0.023(3) 0.024(3) 0.005(2) -0.004(3) 0.001(3) C44 0.067(5) 0.026(3) 0.044(4) 0.009(3) -0.013(4) 0.001(3) C45 0.037(4) 0.065(5) 0.043(4) 0.004(4) -0.010(3) 0.010(4) C46 0.025(3) 0.028(3) 0.047(4) 0.002(3) -0.004(3) -0.014(3) C47 0.021(3) 0.029(3) 0.051(4) 0.003(3) -0.012(3) 0.008(3) C48 0.030(3) 0.025(3) 0.023(3) -0.005(2) -0.002(3) 0.007(3) O4 0.038(3) 0.023(2) 0.055(3) -0.002(2) -0.010(2) 0.0129(19) O5 0.028(2) 0.0103(17) 0.063(3) -0.0006(19) -0.002(2) 0.0004(17) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C1 1.472(7) . ? N1 H1 0.9100 . ? N1 H2 0.9100 . ? N1 H3 0.9100 . ? C1 C2 1.515(8) . ? C1 H4 0.9900 . ? C1 H5 0.9900 . ? C2 O1 1.427(7) . ? C2 C3 1.522(8) . ? C2 H6 1.0000 . ? O1 H7 0.8400 . ? C3 C8 1.369(9) . ? C3 C4 1.398(9) . ? C4 C5 1.387(9) . ? C4 H8 0.9500 . ? C5 C6 1.342(11) . ? C5 H9 0.9500 . ? C6 C7 1.376(12) . ? C6 H10 0.9500 . ? C7 C8 1.398(9) . ? C7 H11 0.9500 . ? C8 H12 0.9500 . ? C9 C10 1.374(10) . ? C9 C14 1.412(9) . ? C9 H13 0.9500 . ? C10 C11 1.353(10) . ? C10 C23 1.541(10) . ? C11 C12 1.381(10) . ? C11 H14 0.9500 . ? C12 C13 1.390(9) . ? C12 H15 0.9500 . ? C13 C14 1.387(9) . ? C13 C18 1.549(8) . ? C14 C15 1.510(9) . ? C15 C16 1.512(9) . ? C15 H16 0.9900 . ? C15 H17 0.9900 . ? C16 C17 1.536(7) . ? C16 H18 0.9900 . ? C16 H19 0.9900 . ? C17 C18 1.555(8) . ? C17 C22 1.558(8) . ? C17 H20 1.0000 . ? C18 C26 1.552(8) . ? C18 C19 1.552(8) . ? C19 C20 1.523(9) . ? C19 H21 0.9900 . ? C19 H22 0.9900 . ? C20 C21 1.538(8) . ? C20 H23 0.9900 . ? C20 H24 0.9900 . ? C21 C22 1.548(8) . ? C21 H25 0.9900 . ? C21 H26 0.9900 . ? C22 C27 1.534(8) . ? C22 C28 1.552(8) . ? C23 C25 1.475(13) . ? C23 C24 1.499(12) . ? C23 H27 1.0000 . ? C24 H28 0.9800 . ? C24 H29 0.9800 . ? C24 H30 0.9800 . ? C25 H31 0.9800 . ? C25 H32 0.9800 . ? C25 H33 0.9800 . ? C26 H34 0.9800 . ? C26 H35 0.9800 . ? C26 H36 0.9800 . ? C27 H37 0.9800 . ? C27 H38 0.9800 . ? C27 H39 0.9800 . ? C28 O3 1.238(7) . ? C28 O2 1.280(7) . ? C29 C34 1.390(8) . ? C29 C30 1.395(8) . ? C29 H40 0.9500 . ? C30 C31 1.404(8) . ? C30 C43 1.508(8) . ? C31 C32 1.380(8) . ? C31 H41 0.9500 . ? C32 C33 1.402(7) . ? C32 H42 0.9500 . ? C33 C34 1.398(8) . ? C33 C38 1.536(8) . ? C34 C35 1.522(7) . ? C35 C36 1.506(9) . ? C35 H43 0.9900 . ? C35 H44 0.9900 . ? C36 C37 1.539(8) . ? C36 H45 0.9900 . ? C36 H46 0.9900 . ? C37 C42 1.549(8) . ? C37 C38 1.567(7) . ? C37 H47 1.0000 . ? C38 C46 1.543(8) . ? C38 C39 1.545(8) . ? C39 C40 1.516(8) . ? C39 H48 0.9900 . ? C39 H49 0.9900 . ? C40 C41 1.527(8) . ? C40 H50 0.9900 . ? C40 H51 0.9900 . ? C41 C42 1.540(8) . ? C41 H52 0.9900 . ? C41 H53 0.9900 . ? C42 C47 1.528(8) . ? C42 C48 1.533(8) . ? C43 C45 1.519(10) . ? C43 C44 1.523(9) . ? C43 H54 1.0000 . ? C44 H55 0.9800 . ? C44 H56 0.9800 . ? C44 H57 0.9800 . ? C45 H58 0.9800 . ? C45 H59 0.9800 . ? C45 H60 0.9800 . ? C46 H61 0.9800 . ? C46 H62 0.9800 . ? C46 H63 0.9800 . ? C47 H64 0.9800 . ? C47 H65 0.9800 . ? C47 H66 0.9800 . ? C48 O4 1.232(7) . ? C48 O5 1.294(7) . ? O5 H67 0.8400 . ? 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 C1 N1 H1 109.5 . . ? C1 N1 H2 109.5 . . ? H1 N1 H2 109.5 . . ? C1 N1 H3 109.5 . . ? H1 N1 H3 109.5 . . ? H2 N1 H3 109.5 . . ? N1 C1 C2 111.3(5) . . ? N1 C1 H4 109.4 . . ? C2 C1 H4 109.4 . . ? N1 C1 H5 109.4 . . ? C2 C1 H5 109.4 . . ? H4 C1 H5 108.0 . . ? O1 C2 C1 107.1(4) . . ? O1 C2 C3 112.0(5) . . ? C1 C2 C3 109.3(5) . . ? O1 C2 H6 109.5 . . ? C1 C2 H6 109.5 . . ? C3 C2 H6 109.5 . . ? C2 O1 H7 109.5 . . ? C8 C3 C4 120.1(6) . . ? C8 C3 C2 121.4(6) . . ? C4 C3 C2 118.5(6) . . ? C5 C4 C3 118.2(7) . . ? C5 C4 H8 120.9 . . ? C3 C4 H8 120.9 . . ? C6 C5 C4 122.1(7) . . ? C6 C5 H9 118.9 . . ? C4 C5 H9 118.9 . . ? C5 C6 C7 120.0(6) . . ? C5 C6 H10 120.0 . . ? C7 C6 H10 120.0 . . ? C6 C7 C8 119.6(7) . . ? C6 C7 H11 120.2 . . ? C8 C7 H11 120.2 . . ? C3 C8 C7 120.0(7) . . ? C3 C8 H12 120.0 . . ? C7 C8 H12 120.0 . . ? C10 C9 C14 121.7(6) . . ? C10 C9 H13 119.2 . . ? C14 C9 H13 119.2 . . ? C11 C10 C9 118.7(7) . . ? C11 C10 C23 119.9(7) . . ? C9 C10 C23 121.3(7) . . ? C10 C11 C12 120.6(6) . . ? C10 C11 H14 119.7 . . ? C12 C11 H14 119.7 . . ? C11 C12 C13 122.1(6) . . ? C11 C12 H15 118.9 . . ? C13 C12 H15 118.9 . . ? C14 C13 C12 117.5(6) . . ? C14 C13 C18 121.9(6) . . ? C12 C13 C18 120.4(5) . . ? C13 C14 C9 119.2(6) . . ? C13 C14 C15 123.1(6) . . ? C9 C14 C15 117.7(6) . . ? C14 C15 C16 113.3(5) . . ? C14 C15 H16 108.9 . . ? C16 C15 H16 108.9 . . ? C14 C15 H17 108.9 . . ? C16 C15 H17 108.9 . . ? H16 C15 H17 107.7 . . ? C15 C16 C17 109.4(5) . . ? C15 C16 H18 109.8 . . ? C17 C16 H18 109.8 . . ? C15 C16 H19 109.8 . . ? C17 C16 H19 109.8 . . ? H18 C16 H19 108.2 . . ? C16 C17 C18 110.0(4) . . ? C16 C17 C22 114.2(4) . . ? C18 C17 C22 116.5(4) . . ? C16 C17 H20 105.0 . . ? C18 C17 H20 105.0 . . ? C22 C17 H20 105.0 . . ? C13 C18 C26 107.1(5) . . ? C13 C18 C19 109.8(5) . . ? C26 C18 C19 109.7(5) . . ? C13 C18 C17 107.5(5) . . ? C26 C18 C17 114.7(5) . . ? C19 C18 C17 108.1(4) . . ? C20 C19 C18 111.8(5) . . ? C20 C19 H21 109.3 . . ? C18 C19 H21 109.3 . . ? C20 C19 H22 109.3 . . ? C18 C19 H22 109.3 . . ? H21 C19 H22 107.9 . . ? C19 C20 C21 113.1(5) . . ? C19 C20 H23 109.0 . . ? C21 C20 H23 109.0 . . ? C19 C20 H24 109.0 . . ? C21 C20 H24 109.0 . . ? H23 C20 H24 107.8 . . ? C20 C21 C22 111.5(5) . . ? C20 C21 H25 109.3 . . ? C22 C21 H25 109.3 . . ? C20 C21 H26 109.3 . . ? C22 C21 H26 109.3 . . ? H25 C21 H26 108.0 . . ? C27 C22 C21 111.2(5) . . ? C27 C22 C28 110.1(5) . . ? C21 C22 C28 105.1(4) . . ? C27 C22 C17 113.8(5) . . ? C21 C22 C17 108.2(5) . . ? C28 C22 C17 108.1(4) . . ? C25 C23 C24 111.6(9) . . ? C25 C23 C10 111.5(7) . . ? C24 C23 C10 112.8(7) . . ? C25 C23 H27 106.8 . . ? C24 C23 H27 106.8 . . ? C10 C23 H27 106.8 . . ? C23 C24 H28 109.5 . . ? C23 C24 H29 109.5 . . ? H28 C24 H29 109.5 . . ? C23 C24 H30 109.5 . . ? H28 C24 H30 109.5 . . ? H29 C24 H30 109.5 . . ? C23 C25 H31 109.5 . . ? C23 C25 H32 109.5 . . ? H31 C25 H32 109.5 . . ? C23 C25 H33 109.5 . . ? H31 C25 H33 109.5 . . ? H32 C25 H33 109.5 . . ? C18 C26 H34 109.5 . . ? C18 C26 H35 109.5 . . ? H34 C26 H35 109.5 . . ? C18 C26 H36 109.5 . . ? H34 C26 H36 109.5 . . ? H35 C26 H36 109.5 . . ? C22 C27 H37 109.5 . . ? C22 C27 H38 109.5 . . ? H37 C27 H38 109.5 . . ? C22 C27 H39 109.5 . . ? H37 C27 H39 109.5 . . ? H38 C27 H39 109.5 . . ? O3 C28 O2 122.1(5) . . ? O3 C28 C22 119.7(5) . . ? O2 C28 C22 118.3(5) . . ? C34 C29 C30 123.3(5) . . ? C34 C29 H40 118.4 . . ? C30 C29 H40 118.4 . . ? C29 C30 C31 116.6(5) . . ? C29 C30 C43 121.6(5) . . ? C31 C30 C43 121.8(5) . . ? C32 C31 C30 120.9(5) . . ? C32 C31 H41 119.6 . . ? C30 C31 H41 119.6 . . ? C31 C32 C33 121.9(5) . . ? C31 C32 H42 119.0 . . ? C33 C32 H42 119.0 . . ? C34 C33 C32 117.9(5) . . ? C34 C33 C38 122.9(5) . . ? C32 C33 C38 119.0(5) . . ? C29 C34 C33 119.4(5) . . ? C29 C34 C35 118.5(5) . . ? C33 C34 C35 122.1(5) . . ? C36 C35 C34 113.7(5) . . ? C36 C35 H43 108.8 . . ? C34 C35 H43 108.8 . . ? C36 C35 H44 108.8 . . ? C34 C35 H44 108.8 . . ? H43 C35 H44 107.7 . . ? C35 C36 C37 109.0(5) . . ? C35 C36 H45 109.9 . . ? C37 C36 H45 109.9 . . ? C35 C36 H46 109.9 . . ? C37 C36 H46 109.9 . . ? H45 C36 H46 108.3 . . ? C36 C37 C42 113.4(4) . . ? C36 C37 C38 110.6(4) . . ? C42 C37 C38 116.0(4) . . ? C36 C37 H47 105.2 . . ? C42 C37 H47 105.2 . . ? C38 C37 H47 105.2 . . ? C33 C38 C46 107.9(5) . . ? C33 C38 C39 111.2(5) . . ? C46 C38 C39 108.8(5) . . ? C33 C38 C37 106.6(4) . . ? C46 C38 C37 116.0(5) . . ? C39 C38 C37 106.3(4) . . ? C40 C39 C38 114.0(5) . . ? C40 C39 H48 108.8 . . ? C38 C39 H48 108.8 . . ? C40 C39 H49 108.8 . . ? C38 C39 H49 108.8 . . ? H48 C39 H49 107.7 . . ? C39 C40 C41 111.5(5) . . ? C39 C40 H50 109.3 . . ? C41 C40 H50 109.3 . . ? C39 C40 H51 109.3 . . ? C41 C40 H51 109.3 . . ? H50 C40 H51 108.0 . . ? C40 C41 C42 112.1(5) . . ? C40 C41 H52 109.2 . . ? C42 C41 H52 109.2 . . ? C40 C41 H53 109.2 . . ? C42 C41 H53 109.2 . . ? H52 C41 H53 107.9 . . ? C47 C42 C48 108.0(5) . . ? C47 C42 C41 111.5(5) . . ? C48 C42 C41 105.4(5) . . ? C47 C42 C37 115.6(5) . . ? C48 C42 C37 107.6(4) . . ? C41 C42 C37 108.2(4) . . ? C30 C43 C45 110.3(5) . . ? C30 C43 C44 112.8(5) . . ? C45 C43 C44 111.1(6) . . ? C30 C43 H54 107.5 . . ? C45 C43 H54 107.5 . . ? C44 C43 H54 107.5 . . ? C43 C44 H55 109.5 . . ? C43 C44 H56 109.5 . . ? H55 C44 H56 109.5 . . ? C43 C44 H57 109.5 . . ? H55 C44 H57 109.5 . . ? H56 C44 H57 109.5 . . ? C43 C45 H58 109.5 . . ? C43 C45 H59 109.5 . . ? H58 C45 H59 109.5 . . ? C43 C45 H60 109.5 . . ? H58 C45 H60 109.5 . . ? H59 C45 H60 109.5 . . ? C38 C46 H61 109.5 . . ? C38 C46 H62 109.5 . . ? H61 C46 H62 109.5 . . ? C38 C46 H63 109.5 . . ? H61 C46 H63 109.5 . . ? H62 C46 H63 109.5 . . ? C42 C47 H64 109.5 . . ? C42 C47 H65 109.5 . . ? H64 C47 H65 109.5 . . ? C42 C47 H66 109.5 . . ? H64 C47 H66 109.5 . . ? H65 C47 H66 109.5 . . ? O4 C48 O5 122.9(5) . . ? O4 C48 C42 122.3(5) . . ? O5 C48 C42 114.8(5) . . ? C48 O5 H67 109.5 . . ? 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 N1 C1 C2 O1 56.0(6) . . . . ? N1 C1 C2 C3 177.5(5) . . . . ? O1 C2 C3 C8 14.3(8) . . . . ? C1 C2 C3 C8 -104.2(7) . . . . ? O1 C2 C3 C4 -169.0(5) . . . . ? C1 C2 C3 C4 72.5(7) . . . . ? C8 C3 C4 C5 -0.6(10) . . . . ? C2 C3 C4 C5 -177.3(6) . . . . ? C3 C4 C5 C6 1.8(11) . . . . ? C4 C5 C6 C7 -1.9(12) . . . . ? C5 C6 C7 C8 0.6(12) . . . . ? C4 C3 C8 C7 -0.6(10) . . . . ? C2 C3 C8 C7 176.0(6) . . . . ? C6 C7 C8 C3 0.6(10) . . . . ? C14 C9 C10 C11 -3.2(11) . . . . ? C14 C9 C10 C23 179.3(7) . . . . ? C9 C10 C11 C12 2.0(11) . . . . ? C23 C10 C11 C12 179.5(6) . . . . ? C10 C11 C12 C13 -1.8(11) . . . . ? C11 C12 C13 C14 2.6(10) . . . . ? C11 C12 C13 C18 177.2(6) . . . . ? C12 C13 C14 C9 -3.7(9) . . . . ? C18 C13 C14 C9 -178.1(6) . . . . ? C12 C13 C14 C15 178.2(6) . . . . ? C18 C13 C14 C15 3.8(10) . . . . ? C10 C9 C14 C13 4.1(10) . . . . ? C10 C9 C14 C15 -177.7(7) . . . . ? C13 C14 C15 C16 -13.0(9) . . . . ? C9 C14 C15 C16 168.8(6) . . . . ? C14 C15 C16 C17 43.6(7) . . . . ? C15 C16 C17 C18 -67.6(6) . . . . ? C15 C16 C17 C22 159.2(5) . . . . ? C14 C13 C18 C26 98.9(6) . . . . ? C12 C13 C18 C26 -75.4(7) . . . . ? C14 C13 C18 C19 -142.1(6) . . . . ? C12 C13 C18 C19 43.6(7) . . . . ? C14 C13 C18 C17 -24.8(8) . . . . ? C12 C13 C18 C17 160.9(5) . . . . ? C16 C17 C18 C13 55.6(6) . . . . ? C22 C17 C18 C13 -172.4(5) . . . . ? C16 C17 C18 C26 -63.3(6) . . . . ? C22 C17 C18 C26 68.7(6) . . . . ? C16 C17 C18 C19 174.1(5) . . . . ? C22 C17 C18 C19 -54.0(6) . . . . ? C13 C18 C19 C20 169.9(5) . . . . ? C26 C18 C19 C20 -72.7(6) . . . . ? C17 C18 C19 C20 53.0(6) . . . . ? C18 C19 C20 C21 -57.2(7) . . . . ? C19 C20 C21 C22 57.1(7) . . . . ? C20 C21 C22 C27 72.9(6) . . . . ? C20 C21 C22 C28 -168.0(5) . . . . ? C20 C21 C22 C17 -52.7(6) . . . . ? C16 C17 C22 C27 60.0(6) . . . . ? C18 C17 C22 C27 -70.0(6) . . . . ? C16 C17 C22 C21 -175.9(5) . . . . ? C18 C17 C22 C21 54.1(6) . . . . ? C16 C17 C22 C28 -62.7(6) . . . . ? C18 C17 C22 C28 167.3(5) . . . . ? C11 C10 C23 C25 -105.0(10) . . . . ? C9 C10 C23 C25 72.5(11) . . . . ? C11 C10 C23 C24 128.5(9) . . . . ? C9 C10 C23 C24 -54.0(10) . . . . ? C27 C22 C28 O3 -153.6(5) . . . . ? C21 C22 C28 O3 86.6(6) . . . . ? C17 C22 C28 O3 -28.7(6) . . . . ? C27 C22 C28 O2 26.3(7) . . . . ? C21 C22 C28 O2 -93.5(6) . . . . ? C17 C22 C28 O2 151.2(4) . . . . ? C34 C29 C30 C31 -0.4(9) . . . . ? C34 C29 C30 C43 -179.4(6) . . . . ? C29 C30 C31 C32 1.0(8) . . . . ? C43 C30 C31 C32 179.9(5) . . . . ? C30 C31 C32 C33 -2.2(9) . . . . ? C31 C32 C33 C34 2.7(8) . . . . ? C31 C32 C33 C38 178.1(5) . . . . ? C30 C29 C34 C33 1.0(9) . . . . ? C30 C29 C34 C35 179.0(6) . . . . ? C32 C33 C34 C29 -2.0(8) . . . . ? C38 C33 C34 C29 -177.2(5) . . . . ? C32 C33 C34 C35 -180.0(5) . . . . ? C38 C33 C34 C35 4.8(9) . . . . ? C29 C34 C35 C36 168.5(5) . . . . ? C33 C34 C35 C36 -13.6(8) . . . . ? C34 C35 C36 C37 43.5(7) . . . . ? C35 C36 C37 C42 159.9(5) . . . . ? C35 C36 C37 C38 -67.8(6) . . . . ? C34 C33 C38 C46 99.7(6) . . . . ? C32 C33 C38 C46 -75.5(6) . . . . ? C34 C33 C38 C39 -141.1(5) . . . . ? C32 C33 C38 C39 43.8(7) . . . . ? C34 C33 C38 C37 -25.6(7) . . . . ? C32 C33 C38 C37 159.3(5) . . . . ? C36 C37 C38 C33 56.2(6) . . . . ? C42 C37 C38 C33 -172.8(5) . . . . ? C36 C37 C38 C46 -63.9(7) . . . . ? C42 C37 C38 C46 67.0(7) . . . . ? C36 C37 C38 C39 175.0(5) . . . . ? C42 C37 C38 C39 -54.1(6) . . . . ? C33 C38 C39 C40 169.2(5) . . . . ? C46 C38 C39 C40 -72.1(6) . . . . ? C37 C38 C39 C40 53.5(6) . . . . ? C38 C39 C40 C41 -57.3(7) . . . . ? C39 C40 C41 C42 56.5(7) . . . . ? C40 C41 C42 C47 74.2(7) . . . . ? C40 C41 C42 C48 -168.9(5) . . . . ? C40 C41 C42 C37 -54.0(6) . . . . ? C36 C37 C42 C47 59.1(7) . . . . ? C38 C37 C42 C47 -70.5(7) . . . . ? C36 C37 C42 C48 -61.7(6) . . . . ? C38 C37 C42 C48 168.7(5) . . . . ? C36 C37 C42 C41 -175.1(5) . . . . ? C38 C37 C42 C41 55.3(6) . . . . ? C29 C30 C43 C45 100.2(7) . . . . ? C31 C30 C43 C45 -78.7(8) . . . . ? C29 C30 C43 C44 -135.0(6) . . . . ? C31 C30 C43 C44 46.1(8) . . . . ? C47 C42 C48 O4 11.4(8) . . . . ? C41 C42 C48 O4 -107.9(6) . . . . ? C37 C42 C48 O4 136.8(6) . . . . ? C47 C42 C48 O5 -171.0(5) . . . . ? C41 C42 C48 O5 69.7(6) . . . . ? C37 C42 C48 O5 -45.6(7) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.437 _refine_diff_density_min -0.550 _refine_diff_density_rms 0.137