# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2011 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'Tu, Yong Qiang' _publ_contact_author_email tuyq@lzu.edu.cn _publ_section_title ; Total Synthesis of (\^A+-)-Maistemonine and (\^A+-)-Stemonamide ; loop_ _publ_author_name 'Zhi-Hua Chen' 'Yong-Qiang Zhang' 'Zhi-Min Chen' 'Yong Qiang Tu' ; Fu-Min Zhang ; # Attachment '- compound 1e.cif' data_p-1 _database_code_depnum_ccdc_archive 'CCDC 782618' #TrackingRef '- compound 1e.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C23 H29 N O6' _chemical_formula_weight 415.47 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.2280(6) _cell_length_b 10.2719(8) _cell_length_c 15.1769(11) _cell_angle_alpha 99.413(5) _cell_angle_beta 99.406(4) _cell_angle_gamma 103.506(4) _cell_volume 1056.75(14) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 1512 _cell_measurement_theta_min 2.78 _cell_measurement_theta_max 21.93 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_min 0.26 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.306 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 444 _exptl_absorpt_coefficient_mu 0.094 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9651 _exptl_absorpt_correction_T_max 0.9759 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 5741 _diffrn_reflns_av_R_equivalents 0.0188 _diffrn_reflns_av_sigmaI/netI 0.0453 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.39 _diffrn_reflns_theta_max 25.50 _reflns_number_total 3903 _reflns_number_gt 2476 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0571P)^2^+0.3250P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3903 _refine_ls_number_parameters 275 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0904 _refine_ls_R_factor_gt 0.0511 _refine_ls_wR_factor_ref 0.1367 _refine_ls_wR_factor_gt 0.1141 _refine_ls_goodness_of_fit_ref 1.004 _refine_ls_restrained_S_all 1.004 _refine_ls_shift/su_max 0.009 _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 -0.1640(3) 0.1022(2) 0.73312(15) 0.0375(5) Uani 1 1 d . . . C2 C -0.1981(3) -0.0249(2) 0.77413(16) 0.0414(6) Uani 1 1 d . . . C3 C -0.1597(4) -0.1537(2) 0.7289(2) 0.0554(7) Uani 1 1 d . . . H3A H -0.1999 -0.1657 0.6633 0.066 Uiso 1 1 calc R . . H3B H -0.2389 -0.2307 0.7471 0.066 Uiso 1 1 calc R . . C4 C 0.0529(4) -0.1561(3) 0.7517(2) 0.0617(8) Uani 1 1 d . . . H4A H 0.0963 -0.1367 0.8176 0.074 Uiso 1 1 calc R . . H4B H 0.0622 -0.2474 0.7281 0.074 Uiso 1 1 calc R . . C5 C 0.1877(4) -0.0545(3) 0.7132(2) 0.0568(7) Uani 1 1 d . . . H5A H 0.1473 -0.0755 0.6472 0.068 Uiso 1 1 calc R . . H5B H 0.3187 -0.0643 0.7285 0.068 Uiso 1 1 calc R . . C6 C 0.1896(3) 0.0938(2) 0.74963(18) 0.0479(6) Uani 1 1 d . . . H6A H 0.1951 0.1055 0.8148 0.057 Uiso 1 1 calc R . . H6B H 0.3092 0.1525 0.7416 0.057 Uiso 1 1 calc R . . C7 C -0.2705(4) -0.0091(3) 0.85022(18) 0.0482(6) Uani 1 1 d . . . C8 C -0.2951(3) 0.1282(3) 0.87186(17) 0.0453(6) Uani 1 1 d . . . C9 C -0.1985(3) 0.2128(2) 0.80873(16) 0.0391(6) Uani 1 1 d . . . C10 C -0.3067(3) 0.0801(3) 0.64139(17) 0.0482(6) Uani 1 1 d . . . H10A H -0.3429 -0.0149 0.6095 0.058 Uiso 1 1 calc R . . H10B H -0.4236 0.1066 0.6506 0.058 Uiso 1 1 calc R . . C11 C -0.1932(4) 0.1725(3) 0.58838(18) 0.0532(7) Uani 1 1 d . . . H11A H -0.2457 0.1436 0.5231 0.064 Uiso 1 1 calc R . . H11B H -0.1923 0.2674 0.6082 0.064 Uiso 1 1 calc R . . C12 C 0.0080(4) 0.1515(3) 0.61335(17) 0.0478(6) Uani 1 1 d . . . H12 H 0.0099 0.0634 0.5777 0.057 Uiso 1 1 calc R . . C13 C -0.0221(3) 0.3233(2) 0.86218(15) 0.0397(6) Uani 1 1 d . . . C14 C -0.0429(4) 0.4484(2) 0.85771(16) 0.0442(6) Uani 1 1 d . . . C15 C -0.2370(4) 0.4274(3) 0.80437(18) 0.0506(7) Uani 1 1 d . . . C16 C -0.3305(5) -0.1128(3) 0.9065(2) 0.0792(10) Uani 1 1 d . . . H16A H -0.3446 -0.2030 0.8720 0.119 Uiso 1 1 calc R . . H16B H -0.4524 -0.1072 0.9220 0.119 Uiso 1 1 calc R . . H16C H -0.2330 -0.0946 0.9614 0.119 Uiso 1 1 calc R . . C17 C 0.3030(4) 0.3711(3) 0.9479(2) 0.0617(8) Uani 1 1 d . . . H17A H 0.3476 0.4207 0.9036 0.093 Uiso 1 1 calc R . . H17B H 0.3936 0.3210 0.9669 0.093 Uiso 1 1 calc R . . H17C H 0.2931 0.4342 0.9999 0.093 Uiso 1 1 calc R . . C18 C 0.0835(4) 0.5916(3) 0.8973(2) 0.0638(8) Uani 1 1 d . . . H18A H 0.1436 0.5981 0.9597 0.096 Uiso 1 1 calc R . . H18B H 0.0052 0.6552 0.8948 0.096 Uiso 1 1 calc R . . H18C H 0.1824 0.6130 0.8627 0.096 Uiso 1 1 calc R . . C19 C 0.1783(4) 0.2632(3) 0.60210(18) 0.0565(7) Uani 1 1 d . . . H19 H 0.2969 0.2325 0.6136 0.068 Uiso 1 1 calc R . . C20 C 0.2182(4) 0.4058(3) 0.65794(19) 0.0605(8) Uani 1 1 d . . . H20A H 0.3026 0.4173 0.7169 0.073 Uiso 1 1 calc R . . H20B H 0.0986 0.4284 0.6669 0.073 Uiso 1 1 calc R . . C21 C 0.3179(5) 0.4904(3) 0.5984(2) 0.0677(8) Uani 1 1 d . . . H21 H 0.4517 0.4821 0.6069 0.081 Uiso 1 1 calc R . . C22 C 0.2161(4) 0.4112(3) 0.5041(2) 0.0603(8) Uani 1 1 d . . . C23 C 0.3318(5) 0.6394(3) 0.6137(2) 0.0797(10) Uani 1 1 d . . . H23A H 0.2035 0.6524 0.6010 0.119 Uiso 1 1 calc R . . H23B H 0.4071 0.6802 0.5738 0.119 Uiso 1 1 calc R . . H23C H 0.3936 0.6819 0.6760 0.119 Uiso 1 1 calc R . . N1 N 0.0279(3) 0.14354(19) 0.70973(13) 0.0397(5) Uani 1 1 d . . . O1 O -0.3781(3) 0.1729(2) 0.92840(13) 0.0658(6) Uani 1 1 d . . . O2 O -0.3253(2) 0.29016(17) 0.77310(12) 0.0489(4) Uani 1 1 d . . . O3 O -0.3240(3) 0.5104(2) 0.78753(15) 0.0761(6) Uani 1 1 d . . . O4 O 0.1153(2) 0.27734(16) 0.90805(11) 0.0479(4) Uani 1 1 d . . . O5 O 0.1413(3) 0.27868(19) 0.50732(13) 0.0664(6) Uani 1 1 d . . . O6 O 0.2006(3) 0.4489(2) 0.43321(15) 0.0822(7) 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 0.0329(12) 0.0362(13) 0.0422(14) 0.0080(11) 0.0116(10) 0.0047(10) C2 0.0362(13) 0.0356(13) 0.0499(15) 0.0069(11) 0.0135(11) 0.0033(10) C3 0.0584(17) 0.0387(15) 0.0690(19) 0.0090(13) 0.0251(14) 0.0064(12) C4 0.0709(19) 0.0465(16) 0.080(2) 0.0176(15) 0.0323(16) 0.0260(14) C5 0.0506(16) 0.0575(17) 0.0720(19) 0.0181(15) 0.0232(14) 0.0231(13) C6 0.0369(13) 0.0512(16) 0.0563(16) 0.0136(13) 0.0134(12) 0.0093(12) C7 0.0475(15) 0.0452(15) 0.0548(16) 0.0162(12) 0.0200(12) 0.0076(12) C8 0.0366(13) 0.0505(16) 0.0476(15) 0.0083(12) 0.0156(12) 0.0061(11) C9 0.0333(12) 0.0407(13) 0.0451(14) 0.0116(11) 0.0105(10) 0.0099(10) C10 0.0414(14) 0.0496(15) 0.0472(15) 0.0066(12) 0.0080(11) 0.0035(11) C11 0.0527(16) 0.0614(17) 0.0413(15) 0.0130(13) 0.0068(12) 0.0079(13) C12 0.0525(15) 0.0477(15) 0.0441(15) 0.0104(12) 0.0185(12) 0.0088(12) C13 0.0375(13) 0.0442(14) 0.0386(13) 0.0094(11) 0.0119(10) 0.0102(11) C14 0.0509(15) 0.0396(14) 0.0419(14) 0.0088(11) 0.0118(11) 0.0101(12) C15 0.0577(17) 0.0457(16) 0.0530(16) 0.0127(13) 0.0155(13) 0.0185(13) C16 0.103(3) 0.068(2) 0.084(2) 0.0376(18) 0.052(2) 0.0200(18) C17 0.0413(15) 0.0595(17) 0.071(2) 0.0041(15) -0.0032(14) 0.0053(13) C18 0.076(2) 0.0408(15) 0.070(2) 0.0107(14) 0.0118(16) 0.0102(14) C19 0.0549(16) 0.0675(19) 0.0559(17) 0.0256(15) 0.0261(13) 0.0151(14) C20 0.0551(17) 0.0667(19) 0.0503(17) 0.0131(14) 0.0142(13) -0.0043(14) C21 0.0678(19) 0.067(2) 0.071(2) 0.0244(16) 0.0215(16) 0.0103(16) C22 0.0618(18) 0.069(2) 0.0575(19) 0.0219(16) 0.0306(15) 0.0135(15) C23 0.079(2) 0.064(2) 0.091(2) 0.0173(18) 0.0191(19) 0.0061(17) N1 0.0347(10) 0.0433(11) 0.0438(12) 0.0127(9) 0.0160(9) 0.0079(9) O1 0.0705(13) 0.0657(13) 0.0698(13) 0.0117(10) 0.0420(11) 0.0179(10) O2 0.0396(9) 0.0482(11) 0.0594(11) 0.0112(9) 0.0066(8) 0.0153(8) O3 0.0818(15) 0.0603(13) 0.0922(16) 0.0185(12) 0.0043(12) 0.0387(12) O4 0.0402(9) 0.0453(10) 0.0524(11) 0.0075(8) -0.0001(8) 0.0091(8) O5 0.0852(14) 0.0640(13) 0.0518(12) 0.0162(9) 0.0353(10) 0.0061(11) O6 0.1004(17) 0.0895(16) 0.0617(14) 0.0341(12) 0.0308(12) 0.0132(13) _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 N1 1.472(3) . ? C1 C2 1.522(3) . ? C1 C10 1.540(3) . ? C1 C9 1.572(3) . ? C2 C7 1.345(3) . ? C2 C3 1.495(3) . ? C3 C4 1.525(4) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 C5 1.513(4) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 C6 1.529(4) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 N1 1.464(3) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 C8 1.454(3) . ? C7 C16 1.502(3) . ? C8 O1 1.215(3) . ? C8 C9 1.539(3) . ? C9 O2 1.442(3) . ? C9 C13 1.502(3) . ? C10 C11 1.524(3) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 C12 1.516(4) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 N1 1.464(3) . ? C12 C19 1.527(3) . ? C12 H12 0.9800 . ? C13 O4 1.339(3) . ? C13 C14 1.339(3) . ? C14 C15 1.450(4) . ? C14 C18 1.505(3) . ? C15 O3 1.207(3) . ? C15 O2 1.372(3) . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 0.9600 . ? C17 O4 1.437(3) . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C19 O5 1.461(3) . ? C19 C20 1.504(4) . ? C19 H19 0.9800 . ? C20 C21 1.506(4) . ? C20 H20A 0.9700 . ? C20 H20B 0.9700 . ? C21 C23 1.487(4) . ? C21 C22 1.498(4) . ? C21 H21 0.9800 . ? C22 O6 1.200(3) . ? C22 O5 1.354(3) . ? C23 H23A 0.9600 . ? C23 H23B 0.9600 . ? C23 H23C 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 N1 C1 C2 114.95(18) . . ? N1 C1 C10 103.21(18) . . ? C2 C1 C10 111.77(18) . . ? N1 C1 C9 112.96(17) . . ? C2 C1 C9 102.50(18) . . ? C10 C1 C9 111.79(19) . . ? C7 C2 C3 125.5(2) . . ? C7 C2 C1 113.5(2) . . ? C3 C2 C1 121.0(2) . . ? C2 C3 C4 114.0(2) . . ? C2 C3 H3A 108.8 . . ? C4 C3 H3A 108.8 . . ? C2 C3 H3B 108.8 . . ? C4 C3 H3B 108.8 . . ? H3A C3 H3B 107.7 . . ? C5 C4 C3 113.8(2) . . ? C5 C4 H4A 108.8 . . ? C3 C4 H4A 108.8 . . ? C5 C4 H4B 108.8 . . ? C3 C4 H4B 108.8 . . ? H4A C4 H4B 107.7 . . ? C4 C5 C6 112.8(2) . . ? C4 C5 H5A 109.0 . . ? C6 C5 H5A 109.0 . . ? C4 C5 H5B 109.0 . . ? C6 C5 H5B 109.0 . . ? H5A C5 H5B 107.8 . . ? N1 C6 C5 118.1(2) . . ? N1 C6 H6A 107.8 . . ? C5 C6 H6A 107.8 . . ? N1 C6 H6B 107.8 . . ? C5 C6 H6B 107.8 . . ? H6A C6 H6B 107.1 . . ? C2 C7 C8 109.9(2) . . ? C2 C7 C16 128.6(3) . . ? C8 C7 C16 121.4(2) . . ? O1 C8 C7 128.0(2) . . ? O1 C8 C9 123.7(2) . . ? C7 C8 C9 108.3(2) . . ? O2 C9 C13 102.54(18) . . ? O2 C9 C8 109.62(18) . . ? C13 C9 C8 110.90(19) . . ? O2 C9 C1 113.43(19) . . ? C13 C9 C1 116.68(18) . . ? C8 C9 C1 103.75(18) . . ? C11 C10 C1 104.00(18) . . ? C11 C10 H10A 111.0 . . ? C1 C10 H10A 111.0 . . ? C11 C10 H10B 111.0 . . ? C1 C10 H10B 111.0 . . ? H10A C10 H10B 109.0 . . ? C12 C11 C10 101.4(2) . . ? C12 C11 H11A 111.5 . . ? C10 C11 H11A 111.5 . . ? C12 C11 H11B 111.5 . . ? C10 C11 H11B 111.5 . . ? H11A C11 H11B 109.3 . . ? N1 C12 C11 103.47(19) . . ? N1 C12 C19 109.6(2) . . ? C11 C12 C19 116.6(2) . . ? N1 C12 H12 109.0 . . ? C11 C12 H12 109.0 . . ? C19 C12 H12 109.0 . . ? O4 C13 C14 133.8(2) . . ? O4 C13 C9 114.4(2) . . ? C14 C13 C9 111.7(2) . . ? C13 C14 C15 106.0(2) . . ? C13 C14 C18 134.2(2) . . ? C15 C14 C18 119.8(2) . . ? O3 C15 O2 120.0(2) . . ? O3 C15 C14 129.6(3) . . ? O2 C15 C14 110.4(2) . . ? C7 C16 H16A 109.5 . . ? C7 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C7 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? O4 C17 H17A 109.5 . . ? O4 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? O4 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C14 C18 H18A 109.5 . . ? C14 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C14 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? O5 C19 C20 104.6(2) . . ? O5 C19 C12 107.8(2) . . ? C20 C19 C12 118.9(2) . . ? O5 C19 H19 108.4 . . ? C20 C19 H19 108.4 . . ? C12 C19 H19 108.4 . . ? C19 C20 C21 101.4(2) . . ? C19 C20 H20A 111.5 . . ? C21 C20 H20A 111.5 . . ? C19 C20 H20B 111.5 . . ? C21 C20 H20B 111.5 . . ? H20A C20 H20B 109.3 . . ? C23 C21 C22 114.6(3) . . ? C23 C21 C20 119.3(3) . . ? C22 C21 C20 102.4(2) . . ? C23 C21 H21 106.6 . . ? C22 C21 H21 106.6 . . ? C20 C21 H21 106.6 . . ? O6 C22 O5 121.2(3) . . ? O6 C22 C21 129.6(3) . . ? O5 C22 C21 109.2(2) . . ? C21 C23 H23A 109.5 . . ? C21 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C21 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C6 N1 C12 117.00(19) . . ? C6 N1 C1 120.62(18) . . ? C12 N1 C1 110.99(18) . . ? C15 O2 C9 109.26(18) . . ? C13 O4 C17 118.71(19) . . ? C22 O5 C19 109.3(2) . . ? 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 C7 131.8(2) . . . . ? C10 C1 C2 C7 -111.0(2) . . . . ? C9 C1 C2 C7 8.9(3) . . . . ? N1 C1 C2 C3 -50.5(3) . . . . ? C10 C1 C2 C3 66.7(3) . . . . ? C9 C1 C2 C3 -173.4(2) . . . . ? C7 C2 C3 C4 -99.5(3) . . . . ? C1 C2 C3 C4 83.1(3) . . . . ? C2 C3 C4 C5 -67.6(3) . . . . ? C3 C4 C5 C6 60.9(3) . . . . ? C4 C5 C6 N1 -78.8(3) . . . . ? C3 C2 C7 C8 -177.8(2) . . . . ? C1 C2 C7 C8 -0.2(3) . . . . ? C3 C2 C7 C16 -0.6(5) . . . . ? C1 C2 C7 C16 177.0(3) . . . . ? C2 C7 C8 O1 170.1(3) . . . . ? C16 C7 C8 O1 -7.3(4) . . . . ? C2 C7 C8 C9 -9.0(3) . . . . ? C16 C7 C8 C9 173.6(2) . . . . ? O1 C8 C9 O2 -43.8(3) . . . . ? C7 C8 C9 O2 135.4(2) . . . . ? O1 C8 C9 C13 68.7(3) . . . . ? C7 C8 C9 C13 -112.1(2) . . . . ? O1 C8 C9 C1 -165.3(2) . . . . ? C7 C8 C9 C1 13.9(2) . . . . ? N1 C1 C9 O2 103.7(2) . . . . ? C2 C1 C9 O2 -132.02(18) . . . . ? C10 C1 C9 O2 -12.2(2) . . . . ? N1 C1 C9 C13 -15.1(3) . . . . ? C2 C1 C9 C13 109.1(2) . . . . ? C10 C1 C9 C13 -131.0(2) . . . . ? N1 C1 C9 C8 -137.42(19) . . . . ? C2 C1 C9 C8 -13.2(2) . . . . ? C10 C1 C9 C8 106.7(2) . . . . ? N1 C1 C10 C11 -26.1(2) . . . . ? C2 C1 C10 C11 -150.1(2) . . . . ? C9 C1 C10 C11 95.6(2) . . . . ? C1 C10 C11 C12 39.8(3) . . . . ? C10 C11 C12 N1 -38.3(2) . . . . ? C10 C11 C12 C19 -158.6(2) . . . . ? O2 C9 C13 O4 175.74(18) . . . . ? C8 C9 C13 O4 58.8(3) . . . . ? C1 C9 C13 O4 -59.7(3) . . . . ? O2 C9 C13 C14 -0.4(3) . . . . ? C8 C9 C13 C14 -117.3(2) . . . . ? C1 C9 C13 C14 124.2(2) . . . . ? O4 C13 C14 C15 -172.8(2) . . . . ? C9 C13 C14 C15 2.3(3) . . . . ? O4 C13 C14 C18 4.6(5) . . . . ? C9 C13 C14 C18 179.7(3) . . . . ? C13 C14 C15 O3 174.7(3) . . . . ? C18 C14 C15 O3 -3.1(4) . . . . ? C13 C14 C15 O2 -3.6(3) . . . . ? C18 C14 C15 O2 178.6(2) . . . . ? N1 C12 C19 O5 -173.5(2) . . . . ? C11 C12 C19 O5 -56.5(3) . . . . ? N1 C12 C19 C20 -54.8(3) . . . . ? C11 C12 C19 C20 62.2(3) . . . . ? O5 C19 C20 C21 -33.5(3) . . . . ? C12 C19 C20 C21 -153.8(2) . . . . ? C19 C20 C21 C23 162.2(3) . . . . ? C19 C20 C21 C22 34.4(3) . . . . ? C23 C21 C22 O6 27.1(5) . . . . ? C20 C21 C22 O6 157.8(3) . . . . ? C23 C21 C22 O5 -155.0(3) . . . . ? C20 C21 C22 O5 -24.3(3) . . . . ? C5 C6 N1 C12 -65.2(3) . . . . ? C5 C6 N1 C1 75.1(3) . . . . ? C11 C12 N1 C6 167.0(2) . . . . ? C19 C12 N1 C6 -67.9(3) . . . . ? C11 C12 N1 C1 23.2(2) . . . . ? C19 C12 N1 C1 148.2(2) . . . . ? C2 C1 N1 C6 -18.6(3) . . . . ? C10 C1 N1 C6 -140.5(2) . . . . ? C9 C1 N1 C6 98.6(2) . . . . ? C2 C1 N1 C12 123.8(2) . . . . ? C10 C1 N1 C12 1.8(2) . . . . ? C9 C1 N1 C12 -119.1(2) . . . . ? O3 C15 O2 C9 -175.0(2) . . . . ? C14 C15 O2 C9 3.4(3) . . . . ? C13 C9 O2 C15 -1.9(2) . . . . ? C8 C9 O2 C15 116.0(2) . . . . ? C1 C9 O2 C15 -128.6(2) . . . . ? C14 C13 O4 C17 -15.9(4) . . . . ? C9 C13 O4 C17 169.1(2) . . . . ? O6 C22 O5 C19 -178.9(3) . . . . ? C21 C22 O5 C19 3.0(3) . . . . ? C20 C19 O5 C22 19.7(3) . . . . ? C12 C19 O5 C22 147.2(2) . . . . ? _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 0.357 _refine_diff_density_min -0.194 _refine_diff_density_rms 0.036 # Attachment '- compound 2.cif' data_cc _database_code_depnum_ccdc_archive 'CCDC 782619' #TrackingRef '- compound 2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H23 N O5' _chemical_formula_weight 357.39 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 Cc loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x, -y, z+1/2' 'x+1/2, y+1/2, z' 'x+1/2, -y+1/2, z+1/2' _cell_length_a 22.90(3) _cell_length_b 9.060(11) _cell_length_c 18.57(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.78(4) _cell_angle_gamma 90.00 _cell_volume 3853(8) _cell_formula_units_Z 8 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 3744 _cell_measurement_theta_min 2.41 _cell_measurement_theta_max 23.25 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.27 _exptl_crystal_size_min 0.24 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.232 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1520 _exptl_absorpt_coefficient_mu 0.089 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9721 _exptl_absorpt_correction_T_max 0.9793 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10696 _diffrn_reflns_av_R_equivalents 0.0333 _diffrn_reflns_av_sigmaI/netI 0.0411 _diffrn_reflns_limit_h_min -28 _diffrn_reflns_limit_h_max 28 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 1.78 _diffrn_reflns_theta_max 26.50 _reflns_number_total 6211 _reflns_number_gt 5062 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0484P)^2^+0.6900P] 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 SHELXL _refine_ls_extinction_coef 0.0004(2) _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 1.9(8) _refine_ls_number_reflns 6211 _refine_ls_number_parameters 476 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0514 _refine_ls_R_factor_gt 0.0394 _refine_ls_wR_factor_ref 0.1020 _refine_ls_wR_factor_gt 0.0937 _refine_ls_goodness_of_fit_ref 1.022 _refine_ls_restrained_S_all 1.022 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.87044(11) 0.1536(4) 0.45652(15) 0.0642(8) Uani 1 1 d . . . C2 C 0.87764(15) 0.3222(4) 0.46445(18) 0.0821(10) Uani 1 1 d . . . H2A H 0.8455 0.3703 0.4392 0.099 Uiso 1 1 calc R . . H2B H 0.9135 0.3516 0.4413 0.099 Uiso 1 1 calc R . . C3 C 0.87937(17) 0.3779(4) 0.5439(2) 0.0935(12) Uani 1 1 d . . . H3A H 0.8824 0.4847 0.5437 0.112 Uiso 1 1 calc R . . H3B H 0.8428 0.3522 0.5665 0.112 Uiso 1 1 calc R . . C4 C 0.93066(13) 0.3136(3) 0.58998(17) 0.0698(8) Uani 1 1 d . . . H4A H 0.9461 0.3896 0.6217 0.084 Uiso 1 1 calc R . . H4B H 0.9165 0.2333 0.6195 0.084 Uiso 1 1 calc R . . C5 C 0.97906(11) 0.2572(3) 0.54123(14) 0.0532(6) Uani 1 1 d . . . C6 C 1.02767(11) 0.3303(3) 0.51957(15) 0.0571(7) Uani 1 1 d . . . C7 C 1.05850(10) 0.2426(3) 0.46452(14) 0.0481(6) Uani 1 1 d . . . C8 C 1.02180(10) 0.0992(2) 0.44981(12) 0.0429(5) Uani 1 1 d . . . C9 C 0.97335(9) 0.1018(2) 0.51033(12) 0.0419(5) Uani 1 1 d . . . C10 C 0.98493(13) -0.0189(3) 0.56796(14) 0.0578(6) Uani 1 1 d . . . H10A H 1.0265 -0.0334 0.5761 0.069 Uiso 1 1 calc R . . H10B H 0.9668 0.0063 0.6132 0.069 Uiso 1 1 calc R . . C11 C 0.95653(14) -0.1572(3) 0.53426(18) 0.0709(8) Uani 1 1 d . . . H11A H 0.9823 -0.2025 0.4997 0.085 Uiso 1 1 calc R . . H11B H 0.9473 -0.2292 0.5710 0.085 Uiso 1 1 calc R . . C12 C 0.90055(12) -0.0997(3) 0.49692(15) 0.0619(7) Uani 1 1 d . . . H12 H 0.8952 -0.1488 0.4503 0.074 Uiso 1 1 calc R . . C13 C 0.84678(15) -0.1231(3) 0.54285(19) 0.0797(10) Uani 1 1 d . . . H13 H 0.8437 -0.0671 0.5846 0.096 Uiso 1 1 calc R . . C14 C 0.80475(18) -0.2159(4) 0.5280(2) 0.1017(13) Uani 1 1 d . . . H14A H 0.8064 -0.2738 0.4867 0.122 Uiso 1 1 calc R . . H14B H 0.7732 -0.2242 0.5587 0.122 Uiso 1 1 calc R . . C15 C 1.05124(16) 0.4786(4) 0.5446(2) 0.0908(11) Uani 1 1 d . . . H15A H 1.0249 0.5213 0.5785 0.136 Uiso 1 1 calc R . . H15B H 1.0549 0.5432 0.5039 0.136 Uiso 1 1 calc R . . H15C H 1.0888 0.4651 0.5671 0.136 Uiso 1 1 calc R . . C16 C 1.06299(12) -0.1032(3) 0.39218(15) 0.0555(6) Uani 1 1 d . . . C17 C 1.02335(11) -0.0342(3) 0.33833(13) 0.0493(6) Uani 1 1 d . . . C18 C 0.99986(10) 0.0852(3) 0.37171(13) 0.0448(5) Uani 1 1 d . . . C19 C 1.01856(15) -0.0982(3) 0.26331(16) 0.0687(8) Uani 1 1 d . . . H19A H 0.9804 -0.1404 0.2562 0.103 Uiso 1 1 calc R . . H19B H 1.0476 -0.1735 0.2576 0.103 Uiso 1 1 calc R . . H19C H 1.0245 -0.0215 0.2285 0.103 Uiso 1 1 calc R . . C20 C 0.92878(14) 0.1731(4) 0.28347(16) 0.0746(9) Uani 1 1 d . . . H20A H 0.9535 0.1871 0.2427 0.112 Uiso 1 1 calc R . . H20B H 0.8975 0.2437 0.2817 0.112 Uiso 1 1 calc R . . H20C H 0.9129 0.0751 0.2824 0.112 Uiso 1 1 calc R . . C1' C 0.28701(11) 0.4076(3) 0.21650(13) 0.0516(6) Uani 1 1 d . . . C2' C 0.24885(12) 0.5463(3) 0.21437(14) 0.0548(6) Uani 1 1 d . . . H2'1 H 0.2148 0.5264 0.1842 0.066 Uiso 1 1 calc R . . H2'2 H 0.2707 0.6249 0.1917 0.066 Uiso 1 1 calc R . . C3' C 0.22769(13) 0.6022(3) 0.28899(15) 0.0603(7) Uani 1 1 d . . . H3'1 H 0.2611 0.6383 0.3164 0.072 Uiso 1 1 calc R . . H3'2 H 0.2012 0.6844 0.2815 0.072 Uiso 1 1 calc R . . C4' C 0.19636(12) 0.4818(3) 0.33369(14) 0.0556(6) Uani 1 1 d . . . H4'1 H 0.2246 0.4304 0.3639 0.067 Uiso 1 1 calc R . . H4'2 H 0.1678 0.5275 0.3646 0.067 Uiso 1 1 calc R . . C5' C 0.16630(10) 0.3729(2) 0.28369(12) 0.0442(5) Uani 1 1 d . . . C6' C 0.11050(11) 0.3798(3) 0.25736(13) 0.0474(6) Uani 1 1 d . . . C7' C 0.10100(10) 0.2623(2) 0.20358(13) 0.0423(5) Uani 1 1 d . . . C8' C 0.16038(10) 0.1812(2) 0.19069(12) 0.0419(5) Uani 1 1 d . . . C9' C 0.20066(10) 0.2400(2) 0.25558(12) 0.0416(5) Uani 1 1 d . . . C10' C 0.20931(12) 0.1186(3) 0.31452(14) 0.0571(7) Uani 1 1 d . . . H10C H 0.2179 0.1623 0.3612 0.069 Uiso 1 1 calc R . . H10D H 0.1749 0.0567 0.3182 0.069 Uiso 1 1 calc R . . C11' C 0.26180(13) 0.0301(3) 0.28693(17) 0.0680(8) Uani 1 1 d . . . H11C H 0.2497 -0.0386 0.2496 0.082 Uiso 1 1 calc R . . H11D H 0.2804 -0.0246 0.3258 0.082 Uiso 1 1 calc R . . C12' C 0.30390(11) 0.1488(3) 0.25642(14) 0.0531(6) Uani 1 1 d . . . H12' H 0.3223 0.1117 0.2126 0.064 Uiso 1 1 calc R . . C13' C 0.35054(13) 0.1944(4) 0.31081(17) 0.0704(8) Uani 1 1 d . . . H13' H 0.3414 0.2708 0.3422 0.084 Uiso 1 1 calc R . . C14' C 0.40270(15) 0.1354(4) 0.3174(2) 0.0924(11) Uani 1 1 d . . . H14C H 0.4137 0.0588 0.2871 0.111 Uiso 1 1 calc R . . H14D H 0.4287 0.1703 0.3524 0.111 Uiso 1 1 calc R . . C15' C 0.06245(13) 0.4858(3) 0.27644(18) 0.0709(8) Uani 1 1 d . . . H15D H 0.0760 0.5511 0.3138 0.106 Uiso 1 1 calc R . . H15E H 0.0292 0.4315 0.2930 0.106 Uiso 1 1 calc R . . H15F H 0.0515 0.5423 0.2347 0.106 Uiso 1 1 calc R . . C16' C 0.16503(11) -0.0419(3) 0.12845(16) 0.0578(6) Uani 1 1 d . . . C17' C 0.18497(10) 0.0735(3) 0.07795(13) 0.0524(6) Uani 1 1 d . . . C18' C 0.18166(10) 0.2030(3) 0.11428(12) 0.0446(5) Uani 1 1 d . . . C19' C 0.20372(13) 0.0292(4) 0.00282(16) 0.0728(8) Uani 1 1 d . . . H19D H 0.1857 0.0938 -0.0320 0.109 Uiso 1 1 calc R . . H19E H 0.1918 -0.0706 -0.0066 0.109 Uiso 1 1 calc R . . H19F H 0.2454 0.0366 -0.0004 0.109 Uiso 1 1 calc R . . C20' C 0.20028(16) 0.3827(4) 0.02093(16) 0.0789(9) Uani 1 1 d . . . H20D H 0.2365 0.3401 0.0059 0.118 Uiso 1 1 calc R . . H20E H 0.2019 0.4880 0.0155 0.118 Uiso 1 1 calc R . . H20F H 0.1689 0.3439 -0.0082 0.118 Uiso 1 1 calc R . . N1 N 0.91313(8) 0.0628(2) 0.48554(11) 0.0507(5) Uani 1 1 d . . . N1' N 0.26308(8) 0.2738(2) 0.23782(10) 0.0449(5) Uani 1 1 d . . . O1 O 0.82655(9) 0.0999(4) 0.42849(13) 0.0998(9) Uani 1 1 d . . . O2 O 1.10417(9) 0.2711(2) 0.43482(11) 0.0694(5) Uani 1 1 d . . . O3 O 1.06186(7) -0.02604(18) 0.45681(9) 0.0521(4) Uani 1 1 d . . . O4 O 1.09470(10) -0.2122(2) 0.38707(12) 0.0788(6) Uani 1 1 d . . . O5 O 0.96288(8) 0.19377(19) 0.34985(9) 0.0550(4) Uani 1 1 d . . . O1' O 0.33967(8) 0.4137(2) 0.20160(12) 0.0710(5) Uani 1 1 d . . . O2' O 0.05497(8) 0.2301(2) 0.17271(10) 0.0616(5) Uani 1 1 d . . . O3' O 0.15063(7) 0.02216(16) 0.19426(9) 0.0520(4) Uani 1 1 d . . . O4' O 0.15980(12) -0.1746(2) 0.11997(14) 0.0894(7) Uani 1 1 d . . . O5' O 0.19048(8) 0.34630(19) 0.09612(9) 0.0581(5) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0384(13) 0.109(2) 0.0454(15) 0.0185(15) 0.0008(11) 0.0038(14) C2 0.0665(19) 0.104(3) 0.076(2) 0.0307(19) 0.0055(16) 0.0359(18) C3 0.091(3) 0.093(2) 0.097(3) 0.0014(19) 0.014(2) 0.042(2) C4 0.0664(17) 0.0752(18) 0.068(2) -0.0137(15) 0.0122(14) 0.0064(15) C5 0.0492(14) 0.0576(14) 0.0528(16) -0.0043(12) -0.0013(11) 0.0028(12) C6 0.0520(15) 0.0536(14) 0.0655(18) -0.0108(12) -0.0026(13) -0.0041(12) C7 0.0422(13) 0.0532(14) 0.0488(14) 0.0030(11) -0.0042(11) -0.0013(10) C8 0.0391(11) 0.0470(13) 0.0425(13) 0.0019(10) -0.0059(10) 0.0053(10) C9 0.0406(12) 0.0481(13) 0.0369(12) 0.0028(10) -0.0044(10) 0.0002(9) C10 0.0614(15) 0.0663(16) 0.0455(15) 0.0137(12) -0.0062(12) 0.0046(13) C11 0.083(2) 0.0553(16) 0.075(2) 0.0164(14) 0.0063(16) -0.0046(15) C12 0.0697(18) 0.0626(16) 0.0536(17) -0.0146(12) 0.0106(13) -0.0228(14) C13 0.091(2) 0.0743(19) 0.075(2) -0.0199(16) 0.0338(18) -0.0273(18) C14 0.096(3) 0.092(2) 0.118(3) -0.017(2) 0.036(2) -0.040(2) C15 0.091(2) 0.0650(19) 0.117(3) -0.0290(18) 0.013(2) -0.0225(17) C16 0.0585(15) 0.0475(14) 0.0606(17) -0.0080(12) 0.0000(12) -0.0016(12) C17 0.0539(14) 0.0498(13) 0.0443(14) -0.0004(11) -0.0020(11) -0.0095(11) C18 0.0419(12) 0.0495(13) 0.0429(13) 0.0070(10) -0.0041(10) -0.0031(10) C19 0.093(2) 0.0636(17) 0.0494(16) -0.0056(13) -0.0041(14) -0.0102(15) C20 0.0671(18) 0.101(2) 0.0547(18) 0.0081(16) -0.0202(14) 0.0057(17) C1' 0.0557(15) 0.0530(14) 0.0462(15) 0.0002(11) -0.0005(12) -0.0130(11) C2' 0.0649(16) 0.0438(13) 0.0555(16) 0.0048(11) -0.0045(12) -0.0123(11) C3' 0.0688(17) 0.0493(14) 0.0626(18) -0.0136(12) -0.0089(13) -0.0087(12) C4' 0.0607(16) 0.0621(15) 0.0440(14) -0.0167(12) -0.0031(12) -0.0071(12) C5' 0.0514(13) 0.0462(12) 0.0350(12) -0.0035(9) 0.0027(10) -0.0062(10) C6' 0.0500(13) 0.0455(13) 0.0466(14) -0.0079(10) 0.0026(11) -0.0025(10) C7' 0.0464(13) 0.0389(11) 0.0414(13) 0.0001(9) -0.0020(10) -0.0066(10) C8' 0.0509(13) 0.0344(11) 0.0406(13) -0.0024(9) -0.0015(10) -0.0055(9) C9' 0.0446(12) 0.0447(12) 0.0354(12) 0.0040(9) -0.0024(9) -0.0058(10) C10' 0.0668(16) 0.0607(15) 0.0437(15) 0.0158(12) -0.0050(12) -0.0116(13) C11' 0.0705(18) 0.0534(15) 0.079(2) 0.0183(14) -0.0192(16) 0.0038(13) C12' 0.0538(14) 0.0523(14) 0.0531(16) -0.0014(11) -0.0021(12) 0.0056(11) C13' 0.0588(17) 0.085(2) 0.067(2) 0.0028(15) -0.0070(14) 0.0079(15) C14' 0.065(2) 0.094(3) 0.118(3) 0.003(2) -0.0196(19) 0.0022(18) C15' 0.0635(17) 0.0656(18) 0.083(2) -0.0271(15) -0.0027(15) 0.0080(14) C16' 0.0539(14) 0.0511(15) 0.0681(18) -0.0194(13) -0.0073(12) 0.0052(12) C17' 0.0406(12) 0.0680(17) 0.0483(15) -0.0176(12) -0.0064(10) 0.0093(11) C18' 0.0406(12) 0.0547(14) 0.0384(13) -0.0035(10) -0.0039(10) -0.0018(10) C19' 0.0585(16) 0.101(2) 0.0594(18) -0.0328(16) 0.0011(13) 0.0170(16) C20' 0.090(2) 0.095(2) 0.0528(18) 0.0142(15) 0.0155(16) -0.0142(18) N1 0.0423(10) 0.0653(13) 0.0443(12) 0.0076(9) -0.0061(9) -0.0083(9) N1' 0.0439(11) 0.0479(11) 0.0428(11) 0.0038(8) -0.0017(9) -0.0015(8) O1 0.0447(11) 0.182(3) 0.0718(15) 0.0215(15) -0.0132(10) -0.0102(13) O2 0.0569(11) 0.0810(13) 0.0705(14) 0.0014(10) 0.0080(10) -0.0168(10) O3 0.0505(9) 0.0533(9) 0.0523(10) -0.0060(8) -0.0110(8) 0.0105(8) O4 0.0906(15) 0.0628(12) 0.0827(15) -0.0185(10) -0.0090(12) 0.0229(11) O5 0.0573(10) 0.0631(10) 0.0443(10) 0.0085(8) -0.0081(8) 0.0038(8) O1' 0.0555(12) 0.0763(13) 0.0814(14) 0.0067(10) 0.0131(10) -0.0169(9) O2' 0.0509(10) 0.0624(11) 0.0711(13) -0.0174(9) -0.0117(9) -0.0078(9) O3' 0.0620(11) 0.0355(8) 0.0584(11) -0.0034(7) 0.0009(8) -0.0063(7) O4' 0.1157(18) 0.0469(11) 0.1054(19) -0.0263(11) -0.0066(14) 0.0030(11) O5' 0.0769(12) 0.0602(11) 0.0372(9) 0.0047(8) -0.0028(8) -0.0126(9) _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 O1 1.226(4) . ? C1 N1 1.381(4) . ? C1 C2 1.543(5) . ? C2 C3 1.559(5) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 C4 1.557(5) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 C5 1.529(4) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 C6 1.361(4) . ? C5 C9 1.526(4) . ? C6 C7 1.482(4) . ? C6 C15 1.519(4) . ? C7 O2 1.217(3) . ? C7 C8 1.569(4) . ? C8 O3 1.464(3) . ? C8 C18 1.534(4) . ? C8 C9 1.590(4) . ? C9 N1 1.491(3) . ? C9 C10 1.551(3) . ? C10 C11 1.540(4) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 C12 1.540(5) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 N1 1.516(4) . ? C12 C13 1.522(4) . ? C12 H12 0.9800 . ? C13 C14 1.305(5) . ? C13 H13 0.9300 . ? C14 H14A 0.9300 . ? C14 H14B 0.9300 . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 0.9600 . ? C16 O4 1.230(3) . ? C16 O3 1.389(3) . ? C16 C17 1.480(4) . ? C17 C18 1.361(4) . ? C17 C19 1.512(4) . ? C18 O5 1.357(3) . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? C20 O5 1.462(4) . ? C20 H20A 0.9600 . ? C20 H20B 0.9600 . ? C20 H20C 0.9600 . ? C1' O1' 1.242(3) . ? C1' N1' 1.390(3) . ? C1' C2' 1.531(4) . ? C2' C3' 1.559(4) . ? C2' H2'1 0.9700 . ? C2' H2'2 0.9700 . ? C3' C4' 1.553(4) . ? C3' H3'1 0.9700 . ? C3' H3'2 0.9700 . ? C4' C5' 1.514(3) . ? C4' H4'1 0.9700 . ? C4' H4'2 0.9700 . ? C5' C6' 1.364(4) . ? C5' C9' 1.534(3) . ? C6' C7' 1.474(3) . ? C6' C15' 1.507(4) . ? C7' O2' 1.228(3) . ? C7' C8' 1.567(4) . ? C8' O3' 1.459(3) . ? C8' C18' 1.520(4) . ? C8' C9' 1.599(3) . ? C9' N1' 1.503(3) . ? C9' C10' 1.562(3) . ? C10' C11' 1.539(4) . ? C10' H10C 0.9700 . ? C10' H10D 0.9700 . ? C11' C12' 1.556(4) . ? C11' H11C 0.9700 . ? C11' H11D 0.9700 . ? C12' N1' 1.506(3) . ? C12' C13' 1.518(4) . ? C12' H12' 0.9800 . ? C13' C14' 1.313(5) . ? C13' H13' 0.9300 . ? C14' H14C 0.9300 . ? C14' H14D 0.9300 . ? C15' H15D 0.9600 . ? C15' H15E 0.9600 . ? C15' H15F 0.9600 . ? C16' O4' 1.218(3) . ? C16' O3' 1.397(3) . ? C16' C17' 1.481(4) . ? C17' C18' 1.356(4) . ? C17' C19' 1.519(4) . ? C18' O5' 1.357(3) . ? C19' H19D 0.9600 . ? C19' H19E 0.9600 . ? C19' H19F 0.9600 . ? C20' O5' 1.455(4) . ? C20' H20D 0.9600 . ? C20' H20E 0.9600 . ? C20' H20F 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 O1 C1 N1 120.1(3) . . ? O1 C1 C2 121.3(3) . . ? N1 C1 C2 118.5(3) . . ? C1 C2 C3 114.3(3) . . ? C1 C2 H2A 108.7 . . ? C3 C2 H2A 108.7 . . ? C1 C2 H2B 108.7 . . ? C3 C2 H2B 108.7 . . ? H2A C2 H2B 107.6 . . ? C4 C3 C2 114.1(3) . . ? C4 C3 H3A 108.7 . . ? C2 C3 H3A 108.7 . . ? C4 C3 H3B 108.7 . . ? C2 C3 H3B 108.7 . . ? H3A C3 H3B 107.6 . . ? C5 C4 C3 110.3(3) . . ? C5 C4 H4A 109.6 . . ? C3 C4 H4A 109.6 . . ? C5 C4 H4B 109.6 . . ? C3 C4 H4B 109.6 . . ? H4A C4 H4B 108.1 . . ? C6 C5 C9 113.8(2) . . ? C6 C5 C4 128.0(2) . . ? C9 C5 C4 118.2(2) . . ? C5 C6 C7 110.0(2) . . ? C5 C6 C15 129.0(3) . . ? C7 C6 C15 121.0(3) . . ? O2 C7 C6 128.3(2) . . ? O2 C7 C8 124.0(2) . . ? C6 C7 C8 107.8(2) . . ? O3 C8 C18 102.52(18) . . ? O3 C8 C7 107.0(2) . . ? C18 C8 C7 113.64(18) . . ? O3 C8 C9 113.02(18) . . ? C18 C8 C9 116.5(2) . . ? C7 C8 C9 104.00(19) . . ? N1 C9 C5 114.14(19) . . ? N1 C9 C10 101.25(19) . . ? C5 C9 C10 112.2(2) . . ? N1 C9 C8 115.5(2) . . ? C5 C9 C8 102.86(18) . . ? C10 C9 C8 111.29(19) . . ? C11 C10 C9 103.0(2) . . ? C11 C10 H10A 111.2 . . ? C9 C10 H10A 111.2 . . ? C11 C10 H10B 111.2 . . ? C9 C10 H10B 111.2 . . ? H10A C10 H10B 109.1 . . ? C12 C11 C10 104.6(2) . . ? C12 C11 H11A 110.8 . . ? C10 C11 H11A 110.8 . . ? C12 C11 H11B 110.8 . . ? C10 C11 H11B 110.8 . . ? H11A C11 H11B 108.9 . . ? N1 C12 C13 111.7(2) . . ? N1 C12 C11 103.5(2) . . ? C13 C12 C11 112.1(3) . . ? N1 C12 H12 109.8 . . ? C13 C12 H12 109.8 . . ? C11 C12 H12 109.8 . . ? C14 C13 C12 124.8(3) . . ? C14 C13 H13 117.6 . . ? C12 C13 H13 117.6 . . ? C13 C14 H14A 120.0 . . ? C13 C14 H14B 120.0 . . ? H14A C14 H14B 120.0 . . ? C6 C15 H15A 109.5 . . ? C6 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C6 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? O4 C16 O3 119.2(2) . . ? O4 C16 C17 130.1(2) . . ? O3 C16 C17 110.7(2) . . ? C18 C17 C16 105.7(2) . . ? C18 C17 C19 134.5(2) . . ? C16 C17 C19 119.8(2) . . ? O5 C18 C17 133.5(2) . . ? O5 C18 C8 114.7(2) . . ? C17 C18 C8 111.7(2) . . ? C17 C19 H19A 109.5 . . ? C17 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C17 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? O5 C20 H20A 109.5 . . ? O5 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? O5 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? O1' C1' N1' 119.4(2) . . ? O1' C1' C2' 120.9(2) . . ? N1' C1' C2' 119.7(2) . . ? C1' C2' C3' 115.4(2) . . ? C1' C2' H2'1 108.4 . . ? C3' C2' H2'1 108.4 . . ? C1' C2' H2'2 108.4 . . ? C3' C2' H2'2 108.4 . . ? H2'1 C2' H2'2 107.5 . . ? C4' C3' C2' 113.5(2) . . ? C4' C3' H3'1 108.9 . . ? C2' C3' H3'1 108.9 . . ? C4' C3' H3'2 108.9 . . ? C2' C3' H3'2 108.9 . . ? H3'1 C3' H3'2 107.7 . . ? C5' C4' C3' 109.8(2) . . ? C5' C4' H4'1 109.7 . . ? C3' C4' H4'1 109.7 . . ? C5' C4' H4'2 109.7 . . ? C3' C4' H4'2 109.7 . . ? H4'1 C4' H4'2 108.2 . . ? C6' C5' C4' 127.3(2) . . ? C6' C5' C9' 113.3(2) . . ? C4' C5' C9' 119.3(2) . . ? C5' C6' C7' 109.8(2) . . ? C5' C6' C15' 129.0(2) . . ? C7' C6' C15' 121.2(2) . . ? O2' C7' C6' 127.3(2) . . ? O2' C7' C8' 123.9(2) . . ? C6' C7' C8' 108.77(19) . . ? O3' C8' C18' 102.84(17) . . ? O3' C8' C7' 108.81(18) . . ? C18' C8' C7' 111.81(19) . . ? O3' C8' C9' 112.43(17) . . ? C18' C8' C9' 118.1(2) . . ? C7' C8' C9' 102.81(18) . . ? N1' C9' C5' 114.09(19) . . ? N1' C9' C10' 100.68(19) . . ? C5' C9' C10' 112.0(2) . . ? N1' C9' C8' 116.31(19) . . ? C5' C9' C8' 102.98(19) . . ? C10' C9' C8' 111.1(2) . . ? C11' C10' C9' 103.0(2) . . ? C11' C10' H10C 111.2 . . ? C9' C10' H10C 111.2 . . ? C11' C10' H10D 111.2 . . ? C9' C10' H10D 111.2 . . ? H10C C10' H10D 109.1 . . ? C10' C11' C12' 104.6(2) . . ? C10' C11' H11C 110.8 . . ? C12' C11' H11C 110.8 . . ? C10' C11' H11D 110.8 . . ? C12' C11' H11D 110.8 . . ? H11C C11' H11D 108.9 . . ? N1' C12' C13' 112.2(2) . . ? N1' C12' C11' 102.6(2) . . ? C13' C12' C11' 112.3(2) . . ? N1' C12' H12' 109.9 . . ? C13' C12' H12' 109.9 . . ? C11' C12' H12' 109.9 . . ? C14' C13' C12' 125.6(3) . . ? C14' C13' H13' 117.2 . . ? C12' C13' H13' 117.2 . . ? C13' C14' H14C 120.0 . . ? C13' C14' H14D 120.0 . . ? H14C C14' H14D 120.0 . . ? C6' C15' H15D 109.5 . . ? C6' C15' H15E 109.5 . . ? H15D C15' H15E 109.5 . . ? C6' C15' H15F 109.5 . . ? H15D C15' H15F 109.5 . . ? H15E C15' H15F 109.5 . . ? O4' C16' O3' 120.0(3) . . ? O4' C16' C17' 130.2(3) . . ? O3' C16' C17' 109.8(2) . . ? C18' C17' C16' 106.0(2) . . ? C18' C17' C19' 134.7(3) . . ? C16' C17' C19' 119.2(2) . . ? O5' C18' C17' 134.0(2) . . ? O5' C18' C8' 114.05(19) . . ? C17' C18' C8' 111.9(2) . . ? C17' C19' H19D 109.5 . . ? C17' C19' H19E 109.5 . . ? H19D C19' H19E 109.5 . . ? C17' C19' H19F 109.5 . . ? H19D C19' H19F 109.5 . . ? H19E C19' H19F 109.5 . . ? O5' C20' H20D 109.5 . . ? O5' C20' H20E 109.5 . . ? H20D C20' H20E 109.5 . . ? O5' C20' H20F 109.5 . . ? H20D C20' H20F 109.5 . . ? H20E C20' H20F 109.5 . . ? C1 N1 C9 128.8(2) . . ? C1 N1 C12 119.9(2) . . ? C9 N1 C12 111.3(2) . . ? C1' N1' C9' 128.33(19) . . ? C1' N1' C12' 118.4(2) . . ? C9' N1' C12' 112.69(19) . . ? C16 O3 C8 109.40(18) . . ? C18 O5 C20 118.9(2) . . ? C16' O3' C8' 109.41(18) . . ? C18' O5' C20' 118.7(2) . . ? 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 O1 C1 C2 C3 114.8(3) . . . . ? N1 C1 C2 C3 -61.5(4) . . . . ? C1 C2 C3 C4 60.7(4) . . . . ? C2 C3 C4 C5 20.7(4) . . . . ? C3 C4 C5 C6 94.4(4) . . . . ? C3 C4 C5 C9 -84.0(3) . . . . ? C9 C5 C6 C7 6.5(3) . . . . ? C4 C5 C6 C7 -172.0(3) . . . . ? C9 C5 C6 C15 -173.1(3) . . . . ? C4 C5 C6 C15 8.4(5) . . . . ? C5 C6 C7 O2 -177.6(3) . . . . ? C15 C6 C7 O2 2.0(4) . . . . ? C5 C6 C7 C8 2.0(3) . . . . ? C15 C6 C7 C8 -178.4(3) . . . . ? O2 C7 C8 O3 50.9(3) . . . . ? C6 C7 C8 O3 -128.7(2) . . . . ? O2 C7 C8 C18 -61.5(3) . . . . ? C6 C7 C8 C18 118.9(2) . . . . ? O2 C7 C8 C9 170.8(2) . . . . ? C6 C7 C8 C9 -8.8(2) . . . . ? C6 C5 C9 N1 -137.6(2) . . . . ? C4 C5 C9 N1 41.1(3) . . . . ? C6 C5 C9 C10 108.0(3) . . . . ? C4 C5 C9 C10 -73.4(3) . . . . ? C6 C5 C9 C8 -11.7(3) . . . . ? C4 C5 C9 C8 166.9(2) . . . . ? O3 C8 C9 N1 -107.7(2) . . . . ? C18 C8 C9 N1 10.7(3) . . . . ? C7 C8 C9 N1 136.64(19) . . . . ? O3 C8 C9 C5 127.4(2) . . . . ? C18 C8 C9 C5 -114.2(2) . . . . ? C7 C8 C9 C5 11.7(2) . . . . ? O3 C8 C9 C10 7.0(3) . . . . ? C18 C8 C9 C10 125.4(2) . . . . ? C7 C8 C9 C10 -108.7(2) . . . . ? N1 C9 C10 C11 38.7(3) . . . . ? C5 C9 C10 C11 160.8(2) . . . . ? C8 C9 C10 C11 -84.5(3) . . . . ? C9 C10 C11 C12 -38.3(3) . . . . ? C10 C11 C12 N1 22.1(3) . . . . ? C10 C11 C12 C13 -98.4(3) . . . . ? N1 C12 C13 C14 133.6(4) . . . . ? C11 C12 C13 C14 -110.8(4) . . . . ? O4 C16 C17 C18 -178.7(3) . . . . ? O3 C16 C17 C18 1.0(3) . . . . ? O4 C16 C17 C19 -1.0(4) . . . . ? O3 C16 C17 C19 178.8(2) . . . . ? C16 C17 C18 O5 177.0(2) . . . . ? C19 C17 C18 O5 -0.3(5) . . . . ? C16 C17 C18 C8 -1.2(3) . . . . ? C19 C17 C18 C8 -178.5(3) . . . . ? O3 C8 C18 O5 -177.55(18) . . . . ? C7 C8 C18 O5 -62.4(3) . . . . ? C9 C8 C18 O5 58.5(3) . . . . ? O3 C8 C18 C17 1.0(2) . . . . ? C7 C8 C18 C17 116.1(2) . . . . ? C9 C8 C18 C17 -123.0(2) . . . . ? O1' C1' C2' C3' -111.0(3) . . . . ? N1' C1' C2' C3' 66.7(3) . . . . ? C1' C2' C3' C4' -53.5(3) . . . . ? C2' C3' C4' C5' -29.9(3) . . . . ? C3' C4' C5' C6' -90.6(3) . . . . ? C3' C4' C5' C9' 87.3(3) . . . . ? C4' C5' C6' C7' 173.0(2) . . . . ? C9' C5' C6' C7' -5.1(3) . . . . ? C4' C5' C6' C15' -7.1(4) . . . . ? C9' C5' C6' C15' 174.9(3) . . . . ? C5' C6' C7' O2' 174.8(2) . . . . ? C15' C6' C7' O2' -5.1(4) . . . . ? C5' C6' C7' C8' -5.3(3) . . . . ? C15' C6' C7' C8' 174.7(2) . . . . ? O2' C7' C8' O3' -48.1(3) . . . . ? C6' C7' C8' O3' 132.0(2) . . . . ? O2' C7' C8' C18' 64.8(3) . . . . ? C6' C7' C8' C18' -115.1(2) . . . . ? O2' C7' C8' C9' -167.5(2) . . . . ? C6' C7' C8' C9' 12.6(2) . . . . ? C6' C5' C9' N1' 139.8(2) . . . . ? C4' C5' C9' N1' -38.4(3) . . . . ? C6' C5' C9' C10' -106.7(2) . . . . ? C4' C5' C9' C10' 75.1(3) . . . . ? C6' C5' C9' C8' 12.8(2) . . . . ? C4' C5' C9' C8' -165.4(2) . . . . ? O3' C8' C9' N1' 103.2(2) . . . . ? C18' C8' C9' N1' -16.4(3) . . . . ? C7' C8' C9' N1' -140.00(19) . . . . ? O3' C8' C9' C5' -131.29(19) . . . . ? C18' C8' C9' C5' 109.2(2) . . . . ? C7' C8' C9' C5' -14.5(2) . . . . ? O3' C8' C9' C10' -11.2(3) . . . . ? C18' C8' C9' C10' -130.8(2) . . . . ? C7' C8' C9' C10' 105.6(2) . . . . ? N1' C9' C10' C11' -37.6(2) . . . . ? C5' C9' C10' C11' -159.2(2) . . . . ? C8' C9' C10' C11' 86.2(3) . . . . ? C9' C10' C11' C12' 39.8(3) . . . . ? C10' C11' C12' N1' -25.1(3) . . . . ? C10' C11' C12' C13' 95.6(3) . . . . ? N1' C12' C13' C14' -152.8(3) . . . . ? C11' C12' C13' C14' 92.3(4) . . . . ? O4' C16' C17' C18' 179.1(3) . . . . ? O3' C16' C17' C18' -0.4(3) . . . . ? O4' C16' C17' C19' -1.2(4) . . . . ? O3' C16' C17' C19' 179.3(2) . . . . ? C16' C17' C18' O5' -175.4(3) . . . . ? C19' C17' C18' O5' 4.9(5) . . . . ? C16' C17' C18' C8' 0.8(3) . . . . ? C19' C17' C18' C8' -178.8(3) . . . . ? O3' C8' C18' O5' 176.14(18) . . . . ? C7' C8' C18' O5' 59.6(2) . . . . ? C9' C8' C18' O5' -59.4(3) . . . . ? O3' C8' C18' C17' -0.9(2) . . . . ? C7' C8' C18' C17' -117.5(2) . . . . ? C9' C8' C18' C17' 123.5(2) . . . . ? O1 C1 N1 C9 168.5(2) . . . . ? C2 C1 N1 C9 -15.2(4) . . . . ? O1 C1 N1 C12 -12.8(4) . . . . ? C2 C1 N1 C12 163.5(2) . . . . ? C5 C9 N1 C1 32.1(3) . . . . ? C10 C9 N1 C1 152.9(3) . . . . ? C8 C9 N1 C1 -86.8(3) . . . . ? C5 C9 N1 C12 -146.8(2) . . . . ? C10 C9 N1 C12 -26.0(2) . . . . ? C8 C9 N1 C12 94.3(2) . . . . ? C13 C12 N1 C1 -55.5(3) . . . . ? C11 C12 N1 C1 -176.2(2) . . . . ? C13 C12 N1 C9 123.5(3) . . . . ? C11 C12 N1 C9 2.8(3) . . . . ? O1' C1' N1' C9' -177.6(2) . . . . ? C2' C1' N1' C9' 4.7(4) . . . . ? O1' C1' N1' C12' 12.1(3) . . . . ? C2' C1' N1' C12' -165.6(2) . . . . ? C5' C9' N1' C1' -27.6(3) . . . . ? C10' C9' N1' C1' -147.7(2) . . . . ? C8' C9' N1' C1' 92.2(3) . . . . ? C5' C9' N1' C12' 143.2(2) . . . . ? C10' C9' N1' C12' 23.1(2) . . . . ? C8' C9' N1' C12' -97.1(2) . . . . ? C13' C12' N1' C1' 51.8(3) . . . . ? C11' C12' N1' C1' 172.5(2) . . . . ? C13' C12' N1' C9' -120.0(2) . . . . ? C11' C12' N1' C9' 0.8(3) . . . . ? O4 C16 O3 C8 179.4(2) . . . . ? C17 C16 O3 C8 -0.4(3) . . . . ? C18 C8 O3 C16 -0.3(2) . . . . ? C7 C8 O3 C16 -120.2(2) . . . . ? C9 C8 O3 C16 125.9(2) . . . . ? C17 C18 O5 C20 16.3(4) . . . . ? C8 C18 O5 C20 -165.6(2) . . . . ? O4' C16' O3' C8' -179.7(2) . . . . ? C17' C16' O3' C8' -0.2(3) . . . . ? C18' C8' O3' C16' 0.6(2) . . . . ? C7' C8' O3' C16' 119.3(2) . . . . ? C9' C8' O3' C16' -127.5(2) . . . . ? C17' C18' O5' C20' 7.5(4) . . . . ? C8' C18' O5' C20' -168.7(2) . . . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 26.50 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.134 _refine_diff_density_min -0.136 _refine_diff_density_rms 0.029