# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2011 data_global _journal_coden_Cambridge 182 loop_ _publ_author_name 'Li, Guangtao' 'Li, Weina' 'Li, Xuesong' 'Zhu, Wei' 'Lin, Changxu' 'Xu, Dan' 'Ju, Yong' _publ_contact_author_name 'Li, Guangtao' _publ_contact_author_email LGT@mail.tsinghua.edu.cn _publ_section_title ; Topochemical approach to efficiently produce main-chain poly(bile acid)s with high molecular weights and adaptive responsive behavior ; # Attachment '- 1.cif' data_juy-15 _database_code_depnum_ccdc_archive 'CCDC 817733' #TrackingRef '- 1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C29 H43 N3 O6' _chemical_formula_sum 'C29 H43 N3 O6' _chemical_formula_weight 529.66 _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 Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) _symmetry_space_group_name_Hall 'P 2ac 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 7.567(3) _cell_length_b 10.377(3) _cell_length_c 35.890(13) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2818.1(16) _cell_formula_units_Z 4 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 73 _cell_measurement_theta_min 2.05 _cell_measurement_theta_max 12.66 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.50 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.248 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1144 _exptl_absorpt_coefficient_mu 0.087 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(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 P4' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 97 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 5141 _diffrn_reflns_av_R_equivalents 0.0420 _diffrn_reflns_av_sigmaI/netI 0.0417 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 1 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -1 _diffrn_reflns_limit_l_max 46 _diffrn_reflns_theta_min 2.04 _diffrn_reflns_theta_max 27.50 _reflns_number_total 3696 _reflns_number_gt 2489 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'XSCANS (Bruker, 1997)' _computing_cell_refinement 'XSCANS (Bruker, 1997)' _computing_data_reduction 'XSCANS (Bruker, 1997)' _computing_structure_solution 'SHELXTL (Bruker, 1997)' _computing_structure_refinement 'SHELXTL (Bruker, 1997)' _computing_molecular_graphics 'SHELXTL (Bruker, 1997)' _computing_publication_material 'SHELXTL (Bruker, 1997)' _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^)+(0.0010P)^2^+2.5000P] 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 3696 _refine_ls_number_parameters 345 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0826 _refine_ls_R_factor_gt 0.0527 _refine_ls_wR_factor_ref 0.1224 _refine_ls_wR_factor_gt 0.1095 _refine_ls_goodness_of_fit_ref 1.053 _refine_ls_restrained_S_all 1.053 _refine_ls_shift/su_max 0.007 _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 O1 O 0.1391(5) 0.6750(3) 0.69270(8) 0.0684(9) Uani 1 1 d . . . O2 O 0.3548(5) 0.7067(4) 0.65066(9) 0.0769(10) Uani 1 1 d . . . O3 O 0.1021(4) 0.3435(3) 0.49434(8) 0.0583(8) Uani 1 1 d . . . H3C H 0.0417 0.3142 0.4774 0.070 Uiso 1 1 calc R . . O4 O 0.6496(5) 0.3241(3) 0.43152(8) 0.0628(9) Uani 1 1 d . . . H4A H 0.6098 0.3012 0.4517 0.075 Uiso 1 1 calc R . . O5 O 0.2652(4) 0.1369(3) 0.33374(7) 0.0584(8) Uani 1 1 d . . . O6 O 0.0791(5) 0.1474(3) 0.28499(9) 0.0724(10) Uani 1 1 d . . . N1 N 0.0799(7) -0.1210(5) 0.27712(13) 0.0808(14) Uani 1 1 d . . . N2 N 0.1336(8) -0.1055(5) 0.24515(14) 0.0901(16) Uani 1 1 d . . . N3 N 0.1688(11) -0.1012(6) 0.21474(14) 0.142(3) Uani 1 1 d . . . C1 C -0.1025(13) 0.8807(8) 0.74308(18) 0.131(3) Uani 1 1 d . . . H1A H -0.2023 0.9108 0.7554 0.157 Uiso 1 1 calc R . . C2 C 0.0214(11) 0.8433(6) 0.72776(14) 0.093(2) Uani 1 1 d . . . C3 C 0.1756(9) 0.8020(5) 0.70764(13) 0.0804(17) Uani 1 1 d . . . H3A H 0.2770 0.7987 0.7242 0.096 Uiso 1 1 calc R . . H3B H 0.2014 0.8617 0.6876 0.096 Uiso 1 1 calc R . . C4 C 0.2469(7) 0.6384(5) 0.66450(11) 0.0566(11) Uani 1 1 d . . . C5 C 0.2103(7) 0.4987(4) 0.65469(11) 0.0618(12) Uani 1 1 d . . . H5A H 0.0835 0.4859 0.6534 0.074 Uiso 1 1 calc R . . H5B H 0.2555 0.4443 0.6745 0.074 Uiso 1 1 calc R . . C6 C 0.2924(7) 0.4561(4) 0.61790(10) 0.0560(11) Uani 1 1 d . . . H6A H 0.2695 0.3648 0.6148 0.067 Uiso 1 1 calc R . . H6B H 0.4194 0.4669 0.6198 0.067 Uiso 1 1 calc R . . C7 C 0.2293(6) 0.5260(4) 0.58246(11) 0.0502(10) Uani 1 1 d . . . H7A H 0.2598 0.6175 0.5847 0.060 Uiso 1 1 calc R . . C8 C 0.0256(6) 0.5148(6) 0.57813(12) 0.0646(13) Uani 1 1 d . . . H8A H -0.0107 0.5578 0.5557 0.097 Uiso 1 1 calc R . . H8B H -0.0311 0.5540 0.5992 0.097 Uiso 1 1 calc R . . H8C H -0.0071 0.4255 0.5768 0.097 Uiso 1 1 calc R . . C9 C 0.3287(5) 0.4703(4) 0.54890(10) 0.0423(9) Uani 1 1 d . . . H9A H 0.3038 0.3777 0.5481 0.051 Uiso 1 1 calc R . . C10 C 0.5326(5) 0.4863(5) 0.55279(11) 0.0527(10) Uani 1 1 d . . . H10A H 0.5602 0.5650 0.5662 0.063 Uiso 1 1 calc R . . H10B H 0.5825 0.4140 0.5663 0.063 Uiso 1 1 calc R . . C11 C 0.6091(5) 0.4918(4) 0.51269(10) 0.0481(10) Uani 1 1 d . . . H11A H 0.6613 0.5754 0.5077 0.058 Uiso 1 1 calc R . . H11B H 0.6982 0.4258 0.5091 0.058 Uiso 1 1 calc R . . C12 C 0.4505(5) 0.4682(4) 0.48747(10) 0.0407(9) Uani 1 1 d . . . H12A H 0.4323 0.3747 0.4870 0.049 Uiso 1 1 calc R . . C13 C 0.2914(5) 0.5258(4) 0.50904(10) 0.0397(8) Uani 1 1 d . . . C14 C 0.1218(5) 0.4803(4) 0.48948(11) 0.0463(9) Uani 1 1 d . . . H14A H 0.0207 0.5233 0.5012 0.056 Uiso 1 1 calc R . . C15 C 0.1249(5) 0.5167(5) 0.44766(11) 0.0507(10) Uani 1 1 d . . . H15A H 0.0213 0.4801 0.4358 0.061 Uiso 1 1 calc R . . H15B H 0.1165 0.6096 0.4455 0.061 Uiso 1 1 calc R . . C16 C 0.2898(5) 0.4714(4) 0.42633(10) 0.0414(8) Uani 1 1 d . . . H16A H 0.2872 0.3770 0.4261 0.050 Uiso 1 1 calc R . . C17 C 0.4610(5) 0.5120(4) 0.44658(10) 0.0397(8) Uani 1 1 d . . . H17A H 0.4671 0.6063 0.4463 0.048 Uiso 1 1 calc R . . C18 C 0.6261(6) 0.4605(4) 0.42729(11) 0.0500(10) Uani 1 1 d . . . H18A H 0.7289 0.5034 0.4384 0.060 Uiso 1 1 calc R . . C19 C 0.6254(6) 0.4908(5) 0.38546(11) 0.0568(11) Uani 1 1 d . . . H19A H 0.6474 0.5822 0.3822 0.068 Uiso 1 1 calc R . . H19B H 0.7222 0.4446 0.3738 0.068 Uiso 1 1 calc R . . C20 C 0.4549(6) 0.4562(4) 0.36528(12) 0.0503(11) Uani 1 1 d . . . H20A H 0.4629 0.4973 0.3408 0.060 Uiso 1 1 calc R . . C21 C 0.2907(5) 0.5171(4) 0.38458(11) 0.0452(9) Uani 1 1 d . . . C22 C 0.1239(6) 0.4722(4) 0.36334(12) 0.0533(11) Uani 1 1 d . . . H22A H 0.0203 0.5032 0.3765 0.064 Uiso 1 1 calc R . . H22B H 0.1240 0.5114 0.3388 0.064 Uiso 1 1 calc R . . C23 C 0.1089(6) 0.3253(4) 0.35879(12) 0.0517(11) Uani 1 1 d . . . H23A H 0.1033 0.2845 0.3831 0.062 Uiso 1 1 calc R . . H23B H 0.0017 0.3040 0.3453 0.062 Uiso 1 1 calc R . . C24 C 0.2690(6) 0.2765(4) 0.33756(11) 0.0531(11) Uani 1 1 d . . . H24A H 0.2706 0.3157 0.3127 0.064 Uiso 1 1 calc R . . C25 C 0.4366(6) 0.3108(5) 0.35765(12) 0.0526(11) Uani 1 1 d . . . H25A H 0.5366 0.2824 0.3429 0.063 Uiso 1 1 calc R . . H25B H 0.4401 0.2648 0.3812 0.063 Uiso 1 1 calc R . . C26 C 0.1692(6) 0.0862(5) 0.30603(12) 0.0547(11) Uani 1 1 d . . . C27 C 0.1927(8) -0.0589(4) 0.30518(13) 0.0664(14) Uani 1 1 d . . . H27A H 0.3154 -0.0788 0.2998 0.080 Uiso 1 1 calc R . . H27B H 0.1648 -0.0939 0.3295 0.080 Uiso 1 1 calc R . . C28 C 0.2955(6) 0.6754(4) 0.51003(12) 0.0529(10) Uani 1 1 d . . . H28A H 0.2724 0.7085 0.4855 0.079 Uiso 1 1 calc R . . H28B H 0.4098 0.7039 0.5182 0.079 Uiso 1 1 calc R . . H28C H 0.2069 0.7062 0.5270 0.079 Uiso 1 1 calc R . . C29 C 0.2969(7) 0.6659(4) 0.38121(12) 0.0623(12) Uani 1 1 d . . . H29A H 0.2969 0.6899 0.3554 0.093 Uiso 1 1 calc R . . H29B H 0.4023 0.6977 0.3929 0.093 Uiso 1 1 calc R . . H29C H 0.1952 0.7024 0.3933 0.093 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.076(2) 0.071(2) 0.0583(17) -0.0141(17) 0.0073(18) -0.003(2) O2 0.086(3) 0.079(2) 0.066(2) -0.0089(18) 0.010(2) -0.023(2) O3 0.057(2) 0.0584(18) 0.0598(17) -0.0047(15) 0.0009(16) -0.0255(17) O4 0.065(2) 0.066(2) 0.0580(17) 0.0030(16) 0.0079(17) 0.0290(19) O5 0.068(2) 0.0560(17) 0.0512(15) -0.0014(14) -0.0111(17) 0.0007(18) O6 0.082(3) 0.077(2) 0.0584(18) -0.0017(18) -0.0176(19) 0.009(2) N1 0.085(4) 0.083(3) 0.074(3) -0.012(3) -0.003(3) -0.030(3) N2 0.111(4) 0.080(3) 0.079(3) -0.004(3) -0.026(3) -0.033(3) N3 0.208(8) 0.151(5) 0.068(3) -0.001(4) -0.024(5) -0.082(6) C1 0.177(9) 0.131(6) 0.085(4) -0.020(4) 0.027(6) 0.040(7) C2 0.140(6) 0.084(4) 0.055(3) -0.016(3) 0.003(4) 0.021(5) C3 0.103(5) 0.076(4) 0.062(3) -0.015(3) -0.016(3) 0.008(4) C4 0.061(3) 0.063(3) 0.046(2) -0.004(2) -0.006(2) 0.002(3) C5 0.069(3) 0.066(3) 0.051(2) 0.001(2) 0.005(2) -0.005(3) C6 0.064(3) 0.055(3) 0.050(2) -0.003(2) 0.003(2) -0.002(3) C7 0.049(2) 0.049(2) 0.054(2) -0.006(2) 0.001(2) 0.000(2) C8 0.052(3) 0.084(4) 0.058(3) 0.000(3) 0.011(2) 0.011(3) C9 0.041(2) 0.0356(19) 0.050(2) -0.0011(18) 0.0010(18) -0.0009(18) C10 0.043(2) 0.061(3) 0.055(2) -0.001(2) -0.006(2) 0.002(2) C11 0.0347(19) 0.051(2) 0.058(2) 0.001(2) -0.0022(18) 0.001(2) C12 0.0307(18) 0.039(2) 0.052(2) 0.0033(18) -0.0006(17) -0.0014(18) C13 0.0336(18) 0.0358(19) 0.050(2) -0.0001(17) 0.0033(17) -0.0004(18) C14 0.0323(19) 0.052(2) 0.054(2) -0.001(2) 0.0030(18) 0.000(2) C15 0.0334(19) 0.063(3) 0.056(2) 0.000(2) -0.0027(19) 0.005(2) C16 0.0299(17) 0.042(2) 0.052(2) 0.0045(18) -0.0005(17) -0.0002(19) C17 0.0285(17) 0.037(2) 0.053(2) 0.0024(19) 0.0010(16) 0.0007(17) C18 0.034(2) 0.061(3) 0.055(2) -0.001(2) 0.0013(19) -0.001(2) C19 0.042(2) 0.066(3) 0.062(2) 0.006(2) 0.011(2) -0.010(3) C20 0.043(2) 0.057(3) 0.051(2) 0.009(2) 0.0031(19) 0.000(2) C21 0.039(2) 0.043(2) 0.053(2) 0.0084(19) -0.0004(19) 0.003(2) C22 0.049(2) 0.059(3) 0.052(2) 0.006(2) -0.005(2) 0.006(2) C23 0.044(2) 0.060(3) 0.051(2) 0.006(2) -0.008(2) -0.001(2) C24 0.062(3) 0.050(2) 0.048(2) 0.0033(19) -0.001(2) -0.001(2) C25 0.047(2) 0.062(3) 0.049(2) 0.000(2) 0.003(2) 0.005(2) C26 0.050(3) 0.064(3) 0.049(2) -0.002(2) 0.002(2) -0.002(2) C27 0.075(4) 0.064(3) 0.061(3) -0.009(2) -0.006(3) -0.002(3) C28 0.053(3) 0.038(2) 0.067(2) 0.000(2) 0.002(2) 0.010(2) C29 0.068(3) 0.051(3) 0.067(3) 0.015(2) -0.004(3) 0.004(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C4 1.355(5) . ? O1 C3 1.449(6) . ? O2 C4 1.189(6) . ? O3 C14 1.438(5) . ? O3 H3C 0.8200 . ? O4 C18 1.435(5) . ? O4 H4A 0.8200 . ? O5 C26 1.339(5) . ? O5 C24 1.455(5) . ? O6 C26 1.200(5) . ? N1 N2 1.228(6) . ? N1 C27 1.469(6) . ? N2 N3 1.124(6) . ? C1 C2 1.154(10) . ? C1 H1A 0.9300 . ? C2 C3 1.438(9) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 C5 1.517(6) . ? C5 C6 1.524(5) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 C7 1.540(6) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 C9 1.533(5) . ? C7 C8 1.553(6) . ? C7 H7A 0.9800 . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? C9 C10 1.558(5) . ? C9 C13 1.568(5) . ? C9 H9A 0.9800 . ? C10 C11 1.552(5) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 C12 1.522(5) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 C17 1.538(5) . ? C12 C13 1.551(5) . ? C12 H12A 0.9800 . ? C13 C14 1.537(5) . ? C13 C28 1.553(5) . ? C14 C15 1.548(5) . ? C14 H14A 0.9800 . ? C15 C16 1.537(5) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 C17 1.544(5) . ? C16 C21 1.571(5) . ? C16 H16A 0.9800 . ? C17 C18 1.525(5) . ? C17 H17A 0.9800 . ? C18 C19 1.534(5) . ? C18 H18A 0.9800 . ? C19 C20 1.523(6) . ? C19 H19A 0.9700 . ? C19 H19B 0.9700 . ? C20 C25 1.540(6) . ? C20 C21 1.557(6) . ? C20 H20A 0.9800 . ? C21 C22 1.546(6) . ? C21 C29 1.550(6) . ? C22 C23 1.538(6) . ? C22 H22A 0.9700 . ? C22 H22B 0.9700 . ? C23 C24 1.518(6) . ? C23 H23A 0.9700 . ? C23 H23B 0.9700 . ? C24 C25 1.501(6) . ? C24 H24A 0.9800 . ? C25 H25A 0.9700 . ? C25 H25B 0.9700 . ? C26 C27 1.516(6) . ? C27 H27A 0.9700 . ? C27 H27B 0.9700 . ? C28 H28A 0.9600 . ? C28 H28B 0.9600 . ? C28 H28C 0.9600 . ? C29 H29A 0.9600 . ? C29 H29B 0.9600 . ? C29 H29C 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 C4 O1 C3 114.6(4) . . ? C14 O3 H3C 109.5 . . ? C18 O4 H4A 109.5 . . ? C26 O5 C24 118.2(4) . . ? N2 N1 C27 113.0(5) . . ? N3 N2 N1 172.2(7) . . ? C2 C1 H1A 180.0 . . ? C1 C2 C3 177.4(8) . . ? C2 C3 O1 107.6(5) . . ? C2 C3 H3A 110.2 . . ? O1 C3 H3A 110.2 . . ? C2 C3 H3B 110.2 . . ? O1 C3 H3B 110.2 . . ? H3A C3 H3B 108.5 . . ? O2 C4 O1 123.9(5) . . ? O2 C4 C5 126.7(5) . . ? O1 C4 C5 109.3(4) . . ? C4 C5 C6 113.8(4) . . ? C4 C5 H5A 108.8 . . ? C6 C5 H5A 108.8 . . ? C4 C5 H5B 108.8 . . ? C6 C5 H5B 108.8 . . ? H5A C5 H5B 107.7 . . ? C5 C6 C7 116.9(4) . . ? C5 C6 H6A 108.1 . . ? C7 C6 H6A 108.1 . . ? C5 C6 H6B 108.1 . . ? C7 C6 H6B 108.1 . . ? H6A C6 H6B 107.3 . . ? C9 C7 C6 108.6(3) . . ? C9 C7 C8 112.3(4) . . ? C6 C7 C8 110.8(4) . . ? C9 C7 H7A 108.3 . . ? C6 C7 H7A 108.3 . . ? C8 C7 H7A 108.3 . . ? C7 C8 H8A 109.5 . . ? C7 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C7 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C7 C9 C10 112.1(3) . . ? C7 C9 C13 119.3(3) . . ? C10 C9 C13 102.8(3) . . ? C7 C9 H9A 107.3 . . ? C10 C9 H9A 107.3 . . ? C13 C9 H9A 107.3 . . ? C11 C10 C9 106.9(3) . . ? C11 C10 H10A 110.4 . . ? C9 C10 H10A 110.4 . . ? C11 C10 H10B 110.4 . . ? C9 C10 H10B 110.4 . . ? H10A C10 H10B 108.6 . . ? C12 C11 C10 104.6(3) . . ? 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 . . ? C11 C12 C17 118.6(3) . . ? C11 C12 C13 104.7(3) . . ? C17 C12 C13 113.7(3) . . ? C11 C12 H12A 106.3 . . ? C17 C12 H12A 106.3 . . ? C13 C12 H12A 106.3 . . ? C14 C13 C12 107.6(3) . . ? C14 C13 C28 109.5(4) . . ? C12 C13 C28 112.4(3) . . ? C14 C13 C9 117.0(3) . . ? C12 C13 C9 100.0(3) . . ? C28 C13 C9 110.0(3) . . ? O3 C14 C13 109.5(3) . . ? O3 C14 C15 111.1(3) . . ? C13 C14 C15 110.8(3) . . ? O3 C14 H14A 108.4 . . ? C13 C14 H14A 108.4 . . ? C15 C14 H14A 108.4 . . ? C16 C15 C14 114.9(3) . . ? C16 C15 H15A 108.5 . . ? C14 C15 H15A 108.5 . . ? C16 C15 H15B 108.5 . . ? C14 C15 H15B 108.5 . . ? H15A C15 H15B 107.5 . . ? C15 C16 C17 111.3(3) . . ? C15 C16 C21 112.7(3) . . ? C17 C16 C21 111.3(3) . . ? C15 C16 H16A 107.1 . . ? C17 C16 H16A 107.1 . . ? C21 C16 H16A 107.1 . . ? C18 C17 C12 111.8(3) . . ? C18 C17 C16 112.2(3) . . ? C12 C17 C16 109.0(3) . . ? C18 C17 H17A 107.9 . . ? C12 C17 H17A 107.9 . . ? C16 C17 H17A 107.9 . . ? O4 C18 C17 113.5(4) . . ? O4 C18 C19 107.8(4) . . ? C17 C18 C19 111.7(4) . . ? O4 C18 H18A 107.9 . . ? C17 C18 H18A 107.9 . . ? C19 C18 H18A 107.9 . . ? C20 C19 C18 114.8(4) . . ? C20 C19 H19A 108.6 . . ? C18 C19 H19A 108.6 . . ? C20 C19 H19B 108.6 . . ? C18 C19 H19B 108.6 . . ? H19A C19 H19B 107.5 . . ? C19 C20 C25 113.1(4) . . ? C19 C20 C21 111.7(3) . . ? C25 C20 C21 113.9(4) . . ? C19 C20 H20A 105.8 . . ? C25 C20 H20A 105.8 . . ? C21 C20 H20A 105.8 . . ? C22 C21 C29 106.7(4) . . ? C22 C21 C20 108.0(3) . . ? C29 C21 C20 110.2(4) . . ? C22 C21 C16 112.1(3) . . ? C29 C21 C16 112.0(3) . . ? C20 C21 C16 107.8(3) . . ? C23 C22 C21 114.3(4) . . ? C23 C22 H22A 108.7 . . ? C21 C22 H22A 108.7 . . ? C23 C22 H22B 108.7 . . ? C21 C22 H22B 108.7 . . ? H22A C22 H22B 107.6 . . ? C24 C23 C22 108.9(4) . . ? C24 C23 H23A 109.9 . . ? C22 C23 H23A 109.9 . . ? C24 C23 H23B 109.9 . . ? C22 C23 H23B 109.9 . . ? H23A C23 H23B 108.3 . . ? O5 C24 C25 107.3(4) . . ? O5 C24 C23 111.3(4) . . ? C25 C24 C23 110.7(3) . . ? O5 C24 H24A 109.1 . . ? C25 C24 H24A 109.1 . . ? C23 C24 H24A 109.1 . . ? C24 C25 C20 113.2(4) . . ? C24 C25 H25A 108.9 . . ? C20 C25 H25A 108.9 . . ? C24 C25 H25B 108.9 . . ? C20 C25 H25B 108.9 . . ? H25A C25 H25B 107.8 . . ? O6 C26 O5 124.6(4) . . ? O6 C26 C27 125.4(5) . . ? O5 C26 C27 110.0(4) . . ? N1 C27 C26 112.4(5) . . ? N1 C27 H27A 109.1 . . ? C26 C27 H27A 109.1 . . ? N1 C27 H27B 109.1 . . ? C26 C27 H27B 109.1 . . ? H27A C27 H27B 107.9 . . ? C13 C28 H28A 109.5 . . ? C13 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? C13 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? C21 C29 H29A 109.5 . . ? C21 C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? C21 C29 H29C 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O4 H4A O3 0.82 2.45 3.199(4) 152.1 4_556 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.211 _refine_diff_density_min -0.204 _refine_diff_density_rms 0.045 # Attachment '- 2.cif' data_juy-13 _database_code_depnum_ccdc_archive 'CCDC 817734' #TrackingRef '- 2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C29 H43 N3 O5' _chemical_formula_sum 'C29 H43 N3 O5' _chemical_formula_weight 513.66 _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 Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) _symmetry_space_group_name_Hall 'P 2ac 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 7.5970(13) _cell_length_b 10.1544(13) _cell_length_c 36.149(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2788.6(8) _cell_formula_units_Z 4 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 46 _cell_measurement_theta_min 4.19 _cell_measurement_theta_max 13.18 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.70 _exptl_crystal_size_mid 0.60 _exptl_crystal_size_min 0.50 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.223 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1112 _exptl_absorpt_coefficient_mu 0.083 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(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 P4' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 97 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 5996 _diffrn_reflns_av_R_equivalents 0.0270 _diffrn_reflns_av_sigmaI/netI 0.0338 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -43 _diffrn_reflns_limit_l_max 43 _diffrn_reflns_theta_min 2.08 _diffrn_reflns_theta_max 25.50 _reflns_number_total 2998 _reflns_number_gt 2539 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'XSCANS (Bruker, 1997)' _computing_cell_refinement 'XSCANS (Bruker, 1997)' _computing_data_reduction 'XSCANS (Bruker, 1997)' _computing_structure_solution 'SHELXTL (Bruker, 1997)' _computing_structure_refinement 'SHELXTL (Bruker, 1997)' _computing_molecular_graphics 'SHELXTL (Bruker, 1997)' _computing_publication_material 'SHELXTL (Bruker, 1997)' _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^)+(0.0010P)^2^+1.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2998 _refine_ls_number_parameters 335 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0465 _refine_ls_R_factor_gt 0.0388 _refine_ls_wR_factor_ref 0.0866 _refine_ls_wR_factor_gt 0.0829 _refine_ls_goodness_of_fit_ref 1.048 _refine_ls_restrained_S_all 1.048 _refine_ls_shift/su_max 0.004 _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 O1 O 0.0801(4) 0.1788(2) 0.71592(6) 0.0759(7) Uani 1 1 d . . . O2 O 0.2654(3) 0.1677(2) 0.66755(5) 0.0606(5) Uani 1 1 d . . . O3 O 0.0850(3) 0.3612(2) 0.51562(6) 0.0633(6) Uani 1 1 d . . . H3C H 0.0913 0.3283 0.4949 0.076 Uiso 1 1 calc R . . O4 O 0.3643(4) 0.6672(2) 0.35087(6) 0.0789(7) Uani 1 1 d . . . O5 O 0.1480(3) 0.6365(2) 0.30948(5) 0.0693(6) Uani 1 1 d . . . N1 N 0.1736(8) -0.0719(4) 0.78585(10) 0.144(2) Uani 1 1 d . . . N2 N 0.1380(6) -0.0782(3) 0.75568(9) 0.0934(11) Uani 1 1 d . . . N3 N 0.0839(5) -0.0952(3) 0.72406(8) 0.0832(10) Uani 1 1 d . . . C1 C 0.1939(5) -0.0314(3) 0.69597(8) 0.0669(9) Uani 1 1 d . . . H1A H 0.1652 -0.0674 0.6719 0.080 Uiso 1 1 calc R . . H1B H 0.3165 -0.0510 0.7010 0.080 Uiso 1 1 calc R . . C2 C 0.1689(4) 0.1170(3) 0.69512(8) 0.0585(8) Uani 1 1 d . . . C3 C 0.4414(4) 0.3411(3) 0.64410(8) 0.0545(7) Uani 1 1 d . . . H3A H 0.4434 0.2919 0.6211 0.065 Uiso 1 1 calc R . . H3B H 0.5396 0.3113 0.6591 0.065 Uiso 1 1 calc R . . C4 C 0.2715(4) 0.3121(3) 0.66427(7) 0.0537(7) Uani 1 1 d . . . H4A H 0.2747 0.3518 0.6890 0.064 Uiso 1 1 calc R . . C5 C 0.1131(4) 0.3631(3) 0.64313(8) 0.0540(7) Uani 1 1 d . . . H5A H 0.0062 0.3461 0.6570 0.065 Uiso 1 1 calc R . . H5B H 0.1042 0.3190 0.6194 0.065 Uiso 1 1 calc R . . C6 C 0.1368(4) 0.5121(3) 0.63740(8) 0.0561(8) Uani 1 1 d . . . H6A H 0.1412 0.5545 0.6614 0.067 Uiso 1 1 calc R . . H6B H 0.0346 0.5460 0.6244 0.067 Uiso 1 1 calc R . . C7 C 0.3034(4) 0.5501(3) 0.61551(8) 0.0499(7) Uani 1 1 d . . . C8 C 0.4653(4) 0.4895(3) 0.63547(8) 0.0526(7) Uani 1 1 d . . . H8A H 0.4767 0.5349 0.6593 0.063 Uiso 1 1 calc R . . C9 C 0.6363(4) 0.5124(3) 0.61437(8) 0.0612(8) Uani 1 1 d . . . H9A H 0.7313 0.4670 0.6270 0.073 Uiso 1 1 calc R . . H9B H 0.6632 0.6058 0.6145 0.073 Uiso 1 1 calc R . . C10 C 0.6270(3) 0.4641(3) 0.57424(7) 0.0538(7) Uani 1 1 d . . . H10A H 0.7349 0.4877 0.5615 0.065 Uiso 1 1 calc R . . H10B H 0.6172 0.3688 0.5740 0.065 Uiso 1 1 calc R . . C11 C 0.4703(3) 0.5234(3) 0.55356(7) 0.0446(6) Uani 1 1 d . . . H11A H 0.4887 0.6186 0.5515 0.054 Uiso 1 1 calc R . . C12 C 0.2967(3) 0.4995(3) 0.57479(7) 0.0439(6) Uani 1 1 d . . . H12A H 0.2820 0.4037 0.5762 0.053 Uiso 1 1 calc R . . C13 C 0.1386(4) 0.5515(3) 0.55287(8) 0.0526(7) Uani 1 1 d . . . H13A H 0.0315 0.5284 0.5660 0.063 Uiso 1 1 calc R . . H13B H 0.1453 0.6469 0.5519 0.063 Uiso 1 1 calc R . . C14 C 0.1267(4) 0.4985(3) 0.51342(8) 0.0473(7) Uani 1 1 d . . . H14A H 0.0303 0.5438 0.5007 0.057 Uiso 1 1 calc R . . C15 C 0.2979(3) 0.5224(2) 0.49171(7) 0.0422(6) Uani 1 1 d . . . C16 C 0.4521(3) 0.4664(3) 0.51460(7) 0.0425(6) Uani 1 1 d . . . H16A H 0.4271 0.3724 0.5178 0.051 Uiso 1 1 calc R . . C17 C 0.6097(4) 0.4742(3) 0.48840(8) 0.0519(7) Uani 1 1 d . . . H17A H 0.6948 0.4058 0.4940 0.062 Uiso 1 1 calc R . . H17B H 0.6670 0.5593 0.4902 0.062 Uiso 1 1 calc R . . C18 C 0.5292(4) 0.4539(3) 0.44969(8) 0.0539(7) Uani 1 1 d . . . H18A H 0.5721 0.3725 0.4389 0.065 Uiso 1 1 calc R . . H18B H 0.5614 0.5262 0.4335 0.065 Uiso 1 1 calc R . . C19 C 0.3262(3) 0.4481(3) 0.45448(7) 0.0444(6) Uani 1 1 d . . . H19A H 0.2953 0.3557 0.4588 0.053 Uiso 1 1 calc R . . C20 C 0.3176(5) 0.7026(3) 0.61701(9) 0.0679(9) Uani 1 1 d . . . H20A H 0.3216 0.7309 0.6423 0.102 Uiso 1 1 calc R . . H20B H 0.2171 0.7410 0.6051 0.102 Uiso 1 1 calc R . . H20C H 0.4230 0.7303 0.6046 0.102 Uiso 1 1 calc R . . C21 C 0.3162(4) 0.6729(2) 0.48503(8) 0.0552(7) Uani 1 1 d . . . H21A H 0.2987 0.7190 0.5079 0.083 Uiso 1 1 calc R . . H21B H 0.2295 0.7009 0.4674 0.083 Uiso 1 1 calc R . . H21C H 0.4317 0.6918 0.4756 0.083 Uiso 1 1 calc R . . C22 C 0.2244(4) 0.4930(3) 0.41982(7) 0.0514(7) Uani 1 1 d . . . H22A H 0.2483 0.5868 0.4160 0.062 Uiso 1 1 calc R . . C23 C 0.0235(4) 0.4757(4) 0.42472(9) 0.0678(9) Uani 1 1 d . . . H23A H -0.0358 0.5050 0.4028 0.102 Uiso 1 1 calc R . . H23B H -0.0156 0.5269 0.4455 0.102 Uiso 1 1 calc R . . H23C H -0.0028 0.3845 0.4290 0.102 Uiso 1 1 calc R . . C24 C 0.2894(4) 0.4184(3) 0.38577(7) 0.0582(8) Uani 1 1 d . . . H24A H 0.2666 0.3254 0.3895 0.070 Uiso 1 1 calc R . . H24B H 0.4159 0.4295 0.3841 0.070 Uiso 1 1 calc R . . C25 C 0.2088(5) 0.4587(3) 0.34872(7) 0.0625(8) Uani 1 1 d . . . H25A H 0.2508 0.3991 0.3297 0.075 Uiso 1 1 calc R . . H25B H 0.0820 0.4493 0.3502 0.075 Uiso 1 1 calc R . . C26 C 0.2522(4) 0.5985(3) 0.33750(8) 0.0593(8) Uani 1 1 d . . . C27 C 0.1886(6) 0.7652(3) 0.29382(9) 0.0805(11) Uani 1 1 d . . . H27A H 0.2140 0.8276 0.3134 0.097 Uiso 1 1 calc R . . H27B H 0.2909 0.7592 0.2778 0.097 Uiso 1 1 calc R . . C28 C 0.0366(7) 0.8081(4) 0.27280(10) 0.0898(13) Uani 1 1 d . . . C29 C -0.0840(9) 0.8458(5) 0.25659(13) 0.133(2) Uani 1 1 d . . . H29A H -0.1814 0.8762 0.2435 0.159 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 O1 0.0860(17) 0.0792(15) 0.0624(13) 0.0007(12) 0.0227(13) 0.0113(15) O2 0.0698(14) 0.0561(12) 0.0558(11) 0.0021(9) 0.0147(11) 0.0028(11) O3 0.0577(13) 0.0617(12) 0.0704(12) 0.0042(11) -0.0009(12) -0.0220(12) O4 0.0871(17) 0.0821(16) 0.0675(13) 0.0124(12) -0.0091(14) -0.0278(16) O5 0.0775(15) 0.0720(14) 0.0585(12) 0.0139(11) -0.0069(12) -0.0041(13) N1 0.205(5) 0.156(4) 0.071(2) 0.000(2) 0.022(3) -0.090(4) N2 0.122(3) 0.087(2) 0.0715(19) 0.0013(18) 0.023(2) -0.042(2) N3 0.094(2) 0.085(2) 0.0709(18) 0.0132(16) 0.0041(19) -0.027(2) C1 0.071(2) 0.066(2) 0.0632(18) 0.0073(16) 0.0100(18) -0.0048(19) C2 0.0577(19) 0.070(2) 0.0480(16) 0.0043(15) -0.0001(15) -0.0012(17) C3 0.0476(16) 0.0595(18) 0.0564(16) 0.0014(15) -0.0028(14) 0.0063(15) C4 0.0601(18) 0.0538(16) 0.0472(14) -0.0024(13) 0.0021(15) 0.0013(16) C5 0.0465(16) 0.0629(18) 0.0527(16) -0.0019(14) 0.0088(14) -0.0010(15) C6 0.0510(16) 0.0621(18) 0.0552(16) -0.0040(15) 0.0056(14) 0.0105(16) C7 0.0460(16) 0.0464(15) 0.0572(15) -0.0062(13) 0.0010(14) 0.0019(14) C8 0.0466(16) 0.0562(17) 0.0549(16) -0.0076(14) -0.0078(13) -0.0013(15) C9 0.0456(16) 0.069(2) 0.0685(18) 0.0022(17) -0.0115(15) -0.0077(17) C10 0.0329(13) 0.0687(19) 0.0598(16) 0.0020(16) -0.0017(13) -0.0030(14) C11 0.0354(13) 0.0431(14) 0.0554(15) 0.0017(13) 0.0007(12) -0.0012(12) C12 0.0360(13) 0.0405(14) 0.0552(14) 0.0001(12) 0.0008(12) 0.0011(12) C13 0.0388(14) 0.0602(17) 0.0589(16) 0.0021(15) 0.0034(13) 0.0085(14) C14 0.0348(13) 0.0476(15) 0.0596(16) 0.0062(13) -0.0034(13) 0.0011(13) C15 0.0376(13) 0.0352(12) 0.0538(14) 0.0047(11) 0.0008(12) -0.0001(12) C16 0.0329(13) 0.0395(13) 0.0551(15) 0.0039(13) 0.0004(12) -0.0010(12) C17 0.0368(14) 0.0552(16) 0.0638(17) 0.0019(15) 0.0026(14) 0.0003(14) C18 0.0457(15) 0.0584(17) 0.0578(16) 0.0022(15) 0.0058(14) 0.0052(15) C19 0.0425(14) 0.0372(13) 0.0533(14) 0.0059(12) 0.0019(12) 0.0002(12) C20 0.078(2) 0.0477(16) 0.078(2) -0.0123(15) -0.001(2) 0.0009(18) C21 0.0576(18) 0.0381(14) 0.0699(17) 0.0051(13) -0.0003(16) 0.0002(14) C22 0.0541(16) 0.0475(15) 0.0527(15) 0.0068(13) -0.0002(14) 0.0029(14) C23 0.0528(17) 0.087(2) 0.0641(19) 0.0004(19) -0.0121(16) 0.0096(19) C24 0.0647(19) 0.0566(17) 0.0533(15) 0.0060(13) 0.0003(16) -0.0021(17) C25 0.072(2) 0.0627(18) 0.0528(16) 0.0017(14) -0.0025(16) -0.0059(19) C26 0.064(2) 0.068(2) 0.0459(15) 0.0032(14) 0.0067(16) -0.0010(18) C27 0.102(3) 0.071(2) 0.069(2) 0.0190(18) 0.010(2) 0.003(2) C28 0.123(4) 0.086(3) 0.061(2) 0.014(2) -0.005(2) 0.014(3) C29 0.174(6) 0.133(4) 0.092(3) 0.022(3) -0.034(4) 0.031(5) _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 O1 C2 1.189(4) . ? O2 C2 1.340(4) . ? O2 C4 1.471(3) . ? O3 C14 1.432(3) . ? O3 H3C 0.8200 . ? O4 C26 1.202(4) . ? O5 C26 1.342(4) . ? O5 C27 1.458(4) . ? N1 N2 1.126(4) . ? N2 N3 1.227(4) . ? N3 C1 1.466(4) . ? C1 C2 1.519(4) . ? C1 H1A 0.9700 . ? C1 H1B 0.9700 . ? C3 C4 1.512(4) . ? C3 C8 1.550(4) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 C5 1.517(4) . ? C4 H4A 0.9800 . ? C5 C6 1.538(4) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 C7 1.542(4) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 C8 1.553(4) . ? C7 C20 1.553(4) . ? C7 C12 1.560(4) . ? C8 C9 1.524(4) . ? C8 H8A 0.9800 . ? C9 C10 1.533(4) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 C11 1.529(4) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 C16 1.529(4) . ? C11 C12 1.545(3) . ? C11 H11A 0.9800 . ? C12 C13 1.533(4) . ? C12 H12A 0.9800 . ? C13 C14 1.527(4) . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C14 C15 1.538(4) . ? C14 H14A 0.9800 . ? C15 C16 1.543(3) . ? C15 C21 1.553(3) . ? C15 C19 1.558(4) . ? C16 C17 1.529(4) . ? C16 H16A 0.9800 . ? C17 C18 1.541(4) . ? C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? C18 C19 1.553(4) . ? C18 H18A 0.9700 . ? C18 H18B 0.9700 . ? C19 C22 1.541(4) . ? C19 H19A 0.9800 . ? C20 H20A 0.9600 . ? C20 H20B 0.9600 . ? C20 H20C 0.9600 . ? C21 H21A 0.9600 . ? C21 H21B 0.9600 . ? C21 H21C 0.9600 . ? C22 C24 1.527(4) . ? C22 C23 1.547(4) . ? C22 H22A 0.9800 . ? C23 H23A 0.9600 . ? C23 H23B 0.9600 . ? C23 H23C 0.9600 . ? C24 C25 1.528(4) . ? C24 H24A 0.9700 . ? C24 H24B 0.9700 . ? C25 C26 1.513(4) . ? C25 H25A 0.9700 . ? C25 H25B 0.9700 . ? C27 C28 1.449(6) . ? C27 H27A 0.9700 . ? C27 H27B 0.9700 . ? C28 C29 1.154(7) . ? C29 H29A 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 O2 C4 117.4(2) . . ? C14 O3 H3C 109.5 . . ? C26 O5 C27 115.2(3) . . ? N1 N2 N3 172.4(4) . . ? N2 N3 C1 113.1(3) . . ? N3 C1 C2 112.4(3) . . ? N3 C1 H1A 109.1 . . ? C2 C1 H1A 109.1 . . ? N3 C1 H1B 109.1 . . ? C2 C1 H1B 109.1 . . ? H1A C1 H1B 107.9 . . ? O1 C2 O2 125.3(3) . . ? O1 C2 C1 125.5(3) . . ? O2 C2 C1 109.1(3) . . ? C4 C3 C8 112.7(3) . . ? C4 C3 H3A 109.0 . . ? C8 C3 H3A 109.0 . . ? C4 C3 H3B 109.0 . . ? C8 C3 H3B 109.0 . . ? H3A C3 H3B 107.8 . . ? O2 C4 C3 105.1(2) . . ? O2 C4 C5 110.9(3) . . ? C3 C4 C5 111.6(2) . . ? O2 C4 H4A 109.7 . . ? C3 C4 H4A 109.7 . . ? C5 C4 H4A 109.7 . . ? C4 C5 C6 108.1(3) . . ? C4 C5 H5A 110.1 . . ? C6 C5 H5A 110.1 . . ? C4 C5 H5B 110.1 . . ? C6 C5 H5B 110.1 . . ? H5A C5 H5B 108.4 . . ? C5 C6 C7 114.3(3) . . ? C5 C6 H6A 108.7 . . ? C7 C6 H6A 108.7 . . ? C5 C6 H6B 108.7 . . ? C7 C6 H6B 108.7 . . ? H6A C6 H6B 107.6 . . ? C6 C7 C8 108.2(2) . . ? C6 C7 C20 106.8(3) . . ? C8 C7 C20 108.9(3) . . ? C6 C7 C12 112.0(2) . . ? C8 C7 C12 109.5(2) . . ? C20 C7 C12 111.4(2) . . ? C9 C8 C3 110.4(3) . . ? C9 C8 C7 112.5(2) . . ? C3 C8 C7 112.8(2) . . ? C9 C8 H8A 106.9 . . ? C3 C8 H8A 106.9 . . ? C7 C8 H8A 106.9 . . ? C8 C9 C10 112.6(2) . . ? C8 C9 H9A 109.1 . . ? C10 C9 H9A 109.1 . . ? C8 C9 H9B 109.1 . . ? C10 C9 H9B 109.1 . . ? H9A C9 H9B 107.8 . . ? C11 C10 C9 111.9(3) . . ? C11 C10 H10A 109.2 . . ? C9 C10 H10A 109.2 . . ? C11 C10 H10B 109.2 . . ? C9 C10 H10B 109.2 . . ? H10A C10 H10B 107.9 . . ? C16 C11 C10 111.8(2) . . ? C16 C11 C12 108.7(2) . . ? C10 C11 C12 111.1(2) . . ? C16 C11 H11A 108.4 . . ? C10 C11 H11A 108.4 . . ? C12 C11 H11A 108.4 . . ? C13 C12 C11 111.0(2) . . ? C13 C12 C7 113.5(2) . . ? C11 C12 C7 112.9(2) . . ? C13 C12 H12A 106.3 . . ? C11 C12 H12A 106.3 . . ? C7 C12 H12A 106.3 . . ? C14 C13 C12 114.1(2) . . ? C14 C13 H13A 108.7 . . ? C12 C13 H13A 108.7 . . ? C14 C13 H13B 108.7 . . ? C12 C13 H13B 108.7 . . ? H13A C13 H13B 107.6 . . ? O3 C14 C13 107.7(2) . . ? O3 C14 C15 111.6(2) . . ? C13 C14 C15 111.8(2) . . ? O3 C14 H14A 108.5 . . ? C13 C14 H14A 108.5 . . ? C15 C14 H14A 108.5 . . ? C14 C15 C16 108.07(19) . . ? C14 C15 C21 108.1(2) . . ? C16 C15 C21 112.2(2) . . ? C14 C15 C19 118.8(2) . . ? C16 C15 C19 100.3(2) . . ? C21 C15 C19 109.3(2) . . ? C11 C16 C17 118.7(2) . . ? C11 C16 C15 115.0(2) . . ? C17 C16 C15 104.1(2) . . ? C11 C16 H16A 106.0 . . ? C17 C16 H16A 106.0 . . ? C15 C16 H16A 106.0 . . ? C16 C17 C18 104.2(2) . . ? C16 C17 H17A 110.9 . . ? C18 C17 H17A 110.9 . . ? C16 C17 H17B 110.9 . . ? C18 C17 H17B 110.9 . . ? H17A C17 H17B 108.9 . . ? C17 C18 C19 107.3(2) . . ? C17 C18 H18A 110.3 . . ? C19 C18 H18A 110.3 . . ? C17 C18 H18B 110.3 . . ? C19 C18 H18B 110.3 . . ? H18A C18 H18B 108.5 . . ? C22 C19 C18 113.4(2) . . ? C22 C19 C15 119.3(2) . . ? C18 C19 C15 102.4(2) . . ? C22 C19 H19A 107.0 . . ? C18 C19 H19A 107.0 . . ? C15 C19 H19A 107.0 . . ? C7 C20 H20A 109.5 . . ? C7 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C7 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C15 C21 H21A 109.5 . . ? C15 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C15 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C24 C22 C19 110.3(2) . . ? C24 C22 C23 110.8(3) . . ? C19 C22 C23 111.6(2) . . ? C24 C22 H22A 108.0 . . ? C19 C22 H22A 108.0 . . ? C23 C22 H22A 108.0 . . ? C22 C23 H23A 109.5 . . ? C22 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C22 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C22 C24 C25 116.4(3) . . ? C22 C24 H24A 108.2 . . ? C25 C24 H24A 108.2 . . ? C22 C24 H24B 108.2 . . ? C25 C24 H24B 108.2 . . ? H24A C24 H24B 107.3 . . ? C26 C25 C24 113.5(3) . . ? C26 C25 H25A 108.9 . . ? C24 C25 H25A 108.9 . . ? C26 C25 H25B 108.9 . . ? C24 C25 H25B 108.9 . . ? H25A C25 H25B 107.7 . . ? O4 C26 O5 123.7(3) . . ? O4 C26 C25 126.2(3) . . ? O5 C26 C25 110.1(3) . . ? C28 C27 O5 107.7(3) . . ? C28 C27 H27A 110.2 . . ? O5 C27 H27A 110.2 . . ? C28 C27 H27B 110.2 . . ? O5 C27 H27B 110.2 . . ? H27A C27 H27B 108.5 . . ? C29 C28 C27 178.0(6) . . ? C28 C29 H29A 180.0 . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.178 _refine_diff_density_min -0.148 _refine_diff_density_rms 0.032 # Attachment '- 3.cif' data_juy-12 _database_code_depnum_ccdc_archive 'CCDC 817735' #TrackingRef '- 3.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C29 H43 N3 O4' _chemical_formula_sum 'C29 H43 N3 O4' _chemical_formula_weight 497.66 _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 Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) _symmetry_space_group_name_Hall 'P 2ac 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 7.6587(13) _cell_length_b 9.9078(13) _cell_length_c 36.420(8) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2763.6(9) _cell_formula_units_Z 4 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 55 _cell_measurement_theta_min 2.20 _cell_measurement_theta_max 16.17 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.60 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.196 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1080 _exptl_absorpt_coefficient_mu 0.079 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(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 P4' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 97 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 3879 _diffrn_reflns_av_R_equivalents 0.0988 _diffrn_reflns_av_sigmaI/netI 0.0746 _diffrn_reflns_limit_h_min -1 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -1 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -1 _diffrn_reflns_limit_l_max 44 _diffrn_reflns_theta_min 2.13 _diffrn_reflns_theta_max 25.52 _reflns_number_total 2955 _reflns_number_gt 1740 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'XSCANS (Bruker, 1997)' _computing_cell_refinement 'XSCANS (Bruker, 1997)' _computing_data_reduction 'XSCANS (Bruker, 1997)' _computing_structure_solution 'SHELXTL (Bruker, 1997)' _computing_structure_refinement 'SHELXTL (Bruker, 1997)' _computing_molecular_graphics 'SHELXTL (Bruker, 1997)' _computing_publication_material 'SHELXTL (Bruker, 1997)' _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^)+(0.0010P)^2^+2.0000P] 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 SHELXL _refine_ls_extinction_coef 0.00473(10) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2955 _refine_ls_number_parameters 326 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1103 _refine_ls_R_factor_gt 0.0628 _refine_ls_wR_factor_ref 0.1338 _refine_ls_wR_factor_gt 0.1159 _refine_ls_goodness_of_fit_ref 1.044 _refine_ls_restrained_S_all 1.044 _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 O1 O 0.0815(3) 0.8126(2) 0.28365(4) 0.0843(7) Uani 1 1 d . . . O2 O 0.2729(2) 0.82223(17) 0.33086(4) 0.0685(6) Uani 1 1 d . . . O3 O 0.3733(3) 0.3484(2) 0.64983(5) 0.0859(6) Uani 1 1 d . . . O4 O 0.1517(3) 0.37444(19) 0.68958(4) 0.0779(6) Uani 1 1 d . . . N1 N 0.0889(3) 1.0918(3) 0.27523(6) 0.0965(9) Uani 1 1 d . . . N2 N 0.1424(4) 1.0745(3) 0.24374(7) 0.1075(10) Uani 1 1 d . . . N3 N 0.1743(5) 1.0685(4) 0.21346(7) 0.1615(14) Uani 1 1 d . . . C1 C 0.2031(4) 1.0245(3) 0.30281(7) 0.0744(9) Uani 1 1 d . . . H1A H 0.3244 1.0418 0.2968 0.089 Uiso 1 1 calc R . . H1B H 0.1803 1.0623 0.3269 0.089 Uiso 1 1 calc R . . C2 C 0.1723(3) 0.8767(3) 0.30377(6) 0.0637(8) Uani 1 1 d . . . C3 C 0.4373(3) 0.6419(3) 0.35548(6) 0.0603(8) Uani 1 1 d . . . H3A H 0.4461 0.6971 0.3774 0.072 Uiso 1 1 calc R . . H3B H 0.5347 0.6646 0.3396 0.072 Uiso 1 1 calc R . . C4 C 0.2690(3) 0.6750(2) 0.33592(6) 0.0617(8) Uani 1 1 d . . . H4A H 0.2692 0.6312 0.3118 0.074 Uiso 1 1 calc R . . C5 C 0.1097(3) 0.6283(3) 0.35727(6) 0.0592(8) Uani 1 1 d . . . H5A H 0.1011 0.6784 0.3801 0.071 Uiso 1 1 calc R . . H5B H 0.0049 0.6454 0.3430 0.071 Uiso 1 1 calc R . . C6 C 0.1246(3) 0.4794(3) 0.36538(6) 0.0651(8) Uani 1 1 d . . . H6A H 0.1251 0.4304 0.3423 0.078 Uiso 1 1 calc R . . H6B H 0.0219 0.4512 0.3790 0.078 Uiso 1 1 calc R . . C7 C 0.2881(3) 0.4394(2) 0.38741(6) 0.0567(7) Uani 1 1 d . . . C8 C 0.4504(3) 0.4924(3) 0.36636(6) 0.0575(7) Uani 1 1 d . . . H8A H 0.4575 0.4407 0.3435 0.069 Uiso 1 1 calc R . . C9 C 0.6200(3) 0.4666(3) 0.38718(6) 0.0702(9) Uani 1 1 d . . . H9A H 0.7162 0.5075 0.3739 0.084 Uiso 1 1 calc R . . H9B H 0.6411 0.3701 0.3884 0.084 Uiso 1 1 calc R . . C10 C 0.6139(3) 0.5252(3) 0.42695(6) 0.0614(8) Uani 1 1 d . . . H10A H 0.7198 0.5002 0.4399 0.074 Uiso 1 1 calc R . . H10B H 0.6092 0.6230 0.4257 0.074 Uiso 1 1 calc R . . C11 C 0.4557(3) 0.4732(3) 0.44818(6) 0.0496(7) Uani 1 1 d . . . H11A H 0.4672 0.3753 0.4512 0.060 Uiso 1 1 calc R . . C12 C 0.2853(3) 0.5025(2) 0.42709(5) 0.0475(6) Uani 1 1 d . . . H12A H 0.2806 0.6006 0.4237 0.057 Uiso 1 1 calc R . . C13 C 0.1237(3) 0.4647(3) 0.44899(6) 0.0719(9) Uani 1 1 d . . . H13A H 0.1162 0.3671 0.4505 0.086 Uiso 1 1 calc R . . H13B H 0.0211 0.4965 0.4360 0.086 Uiso 1 1 calc R . . C14 C 0.1222(3) 0.5238(3) 0.48842(6) 0.0623(8) Uani 1 1 d . . . H14A H 0.1114 0.6212 0.4871 0.075 Uiso 1 1 calc R . . H14B H 0.0216 0.4892 0.5016 0.075 Uiso 1 1 calc R . . C15 C 0.2884(3) 0.4874(2) 0.50944(6) 0.0477(6) Uani 1 1 d . . . C16 C 0.4438(3) 0.5389(2) 0.48666(6) 0.0469(6) Uani 1 1 d . . . H16A H 0.4227 0.6353 0.4825 0.056 Uiso 1 1 calc R . . C17 C 0.6007(3) 0.5304(3) 0.51156(6) 0.0570(7) Uani 1 1 d . . . H17A H 0.6870 0.5980 0.5051 0.068 Uiso 1 1 calc R . . H17B H 0.6541 0.4418 0.5103 0.068 Uiso 1 1 calc R . . C18 C 0.5229(3) 0.5580(3) 0.55077(6) 0.0607(8) Uani 1 1 d . . . H18A H 0.5541 0.4858 0.5675 0.073 Uiso 1 1 calc R . . H18B H 0.5671 0.6424 0.5605 0.073 Uiso 1 1 calc R . . C19 C 0.3223(3) 0.5650(2) 0.54586(6) 0.0522(7) Uani 1 1 d . . . H19A H 0.2931 0.6598 0.5413 0.063 Uiso 1 1 calc R . . C20 C 0.2925(4) 0.2843(2) 0.38856(7) 0.0843(10) Uani 1 1 d . . . H20A H 0.3927 0.2550 0.4022 0.126 Uiso 1 1 calc R . . H20B H 0.2991 0.2496 0.3640 0.126 Uiso 1 1 calc R . . H20C H 0.1883 0.2514 0.4002 0.126 Uiso 1 1 calc R . . C21 C 0.2985(4) 0.3370(2) 0.51671(7) 0.0699(9) Uani 1 1 d . . . H21A H 0.4044 0.3169 0.5297 0.105 Uiso 1 1 calc R . . H21B H 0.2975 0.2891 0.4938 0.105 Uiso 1 1 calc R . . H21C H 0.2000 0.3096 0.5312 0.105 Uiso 1 1 calc R . . C22 C 0.2210(3) 0.5219(3) 0.58105(6) 0.0571(7) Uani 1 1 d . . . H22A H 0.2448 0.4259 0.5853 0.069 Uiso 1 1 calc R . . C23 C 0.0238(3) 0.5379(3) 0.57607(7) 0.0761(9) Uani 1 1 d . . . H23A H -0.0136 0.4862 0.5552 0.114 Uiso 1 1 calc R . . H23B H -0.0036 0.6314 0.5722 0.114 Uiso 1 1 calc R . . H23C H -0.0352 0.5062 0.5977 0.114 Uiso 1 1 calc R . . C24 C 0.2907(4) 0.6010(2) 0.61465(6) 0.0626(8) Uani 1 1 d . . . H24A H 0.4163 0.5896 0.6159 0.075 Uiso 1 1 calc R . . H24B H 0.2673 0.6962 0.6110 0.075 Uiso 1 1 calc R . . C25 C 0.2110(4) 0.5575(3) 0.65155(6) 0.0670(8) Uani 1 1 d . . . H25A H 0.2495 0.6192 0.6706 0.080 Uiso 1 1 calc R . . H25B H 0.0848 0.5635 0.6500 0.080 Uiso 1 1 calc R . . C26 C 0.2604(3) 0.4180(3) 0.66201(6) 0.0625(8) Uani 1 1 d . . . C27 C 0.1947(4) 0.2428(3) 0.70462(7) 0.0857(10) Uani 1 1 d . . . H27A H 0.2973 0.2493 0.7201 0.103 Uiso 1 1 calc R . . H27B H 0.2192 0.1797 0.6849 0.103 Uiso 1 1 calc R . . C28 C 0.0459(5) 0.1965(3) 0.72601(7) 0.0936(12) Uani 1 1 d . . . C29 C -0.0672(5) 0.1547(4) 0.74249(9) 0.1268(16) Uani 1 1 d . . . H29A H -0.1601 0.1204 0.7560 0.152 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 O1 0.0993(13) 0.0942(13) 0.0593(9) 0.0007(10) -0.0291(10) -0.0185(13) O2 0.0844(12) 0.0660(10) 0.0550(8) 0.0037(8) -0.0172(10) -0.0061(11) O3 0.0926(12) 0.0980(13) 0.0670(10) 0.0135(11) 0.0142(11) 0.0352(12) O4 0.0866(12) 0.0833(12) 0.0637(10) 0.0105(10) 0.0123(10) 0.0073(12) N1 0.1097(18) 0.1086(18) 0.0712(14) 0.0088(14) -0.0005(15) 0.0397(17) N2 0.141(2) 0.0999(18) 0.0821(15) 0.0010(15) -0.0275(17) 0.0486(19) N3 0.226(3) 0.190(3) 0.0689(15) 0.005(2) -0.018(2) 0.116(3) C1 0.0880(18) 0.0753(17) 0.0600(14) 0.0083(14) -0.0118(16) 0.0070(19) C2 0.0657(16) 0.0719(17) 0.0534(13) 0.0031(13) -0.0024(14) -0.0019(15) C3 0.0541(14) 0.0791(17) 0.0476(12) -0.0028(13) 0.0035(12) -0.0056(15) C4 0.0785(17) 0.0610(15) 0.0456(12) -0.0045(12) -0.0069(14) -0.0036(16) C5 0.0550(14) 0.0734(16) 0.0491(13) -0.0033(13) -0.0120(12) 0.0083(15) C6 0.0640(14) 0.0763(17) 0.0551(13) -0.0061(14) -0.0131(13) -0.0073(16) C7 0.0589(14) 0.0565(14) 0.0545(12) -0.0097(12) -0.0007(13) -0.0100(14) C8 0.0558(13) 0.0637(16) 0.0529(12) -0.0148(12) 0.0024(12) 0.0050(14) C9 0.0601(14) 0.0854(18) 0.0652(14) -0.0098(16) 0.0108(14) 0.0119(17) C10 0.0431(12) 0.0840(18) 0.0571(13) -0.0042(15) -0.0004(12) -0.0035(15) C11 0.0441(12) 0.0544(14) 0.0504(11) 0.0015(12) -0.0024(11) 0.0019(13) C12 0.0443(11) 0.0473(12) 0.0509(11) 0.0010(11) -0.0011(11) -0.0035(12) C13 0.0473(13) 0.106(2) 0.0620(14) 0.0051(17) -0.0065(13) -0.0172(17) C14 0.0409(12) 0.0908(19) 0.0553(13) 0.0041(15) 0.0061(12) -0.0058(15) C15 0.0446(12) 0.0476(12) 0.0507(11) 0.0023(11) 0.0000(11) -0.0022(12) C16 0.0364(11) 0.0486(13) 0.0556(12) 0.0025(12) -0.0011(11) 0.0048(12) C17 0.0491(13) 0.0655(15) 0.0566(13) -0.0024(13) 0.0001(12) 0.0071(14) C18 0.0524(14) 0.0739(17) 0.0560(13) 0.0000(14) -0.0062(12) 0.0030(15) C19 0.0544(13) 0.0466(13) 0.0555(12) 0.0086(11) -0.0012(12) -0.0045(13) C20 0.108(2) 0.0577(16) 0.0875(18) -0.0094(15) -0.018(2) 0.0031(19) C21 0.0840(19) 0.0588(15) 0.0670(15) 0.0004(13) 0.0046(16) -0.0085(17) C22 0.0636(14) 0.0541(14) 0.0537(12) 0.0088(12) 0.0024(13) -0.0098(14) C23 0.0688(16) 0.096(2) 0.0633(14) -0.0011(17) 0.0159(14) -0.0093(18) C24 0.0726(16) 0.0604(15) 0.0547(12) 0.0003(12) 0.0029(14) 0.0013(16) C25 0.0769(16) 0.0737(16) 0.0504(12) 0.0010(13) 0.0023(14) 0.0145(17) C26 0.0663(16) 0.0772(17) 0.0441(11) -0.0011(13) -0.0058(13) 0.0012(16) C27 0.115(2) 0.0762(18) 0.0663(15) 0.0157(16) -0.0129(18) -0.001(2) C28 0.117(2) 0.102(2) 0.0621(16) 0.0213(17) 0.0062(19) -0.004(2) C29 0.159(4) 0.139(3) 0.083(2) 0.024(2) 0.027(2) -0.029(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C2 1.193(3) . ? O2 C2 1.363(3) . ? O2 C4 1.471(3) . ? O3 C26 1.192(3) . ? O4 C26 1.374(3) . ? O4 C27 1.452(3) . ? N1 N2 1.230(3) . ? N1 C1 1.490(3) . ? N2 N3 1.131(3) . ? C1 C2 1.484(4) . ? C1 H1A 0.9700 . ? C1 H1B 0.9700 . ? C3 C4 1.509(3) . ? C3 C8 1.537(4) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 C5 1.519(3) . ? C4 H4A 0.9800 . ? C5 C6 1.510(4) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 C7 1.539(3) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 C20 1.538(3) . ? C7 C8 1.552(3) . ? C7 C12 1.575(3) . ? C8 C9 1.526(3) . ? C8 H8A 0.9800 . ? C9 C10 1.562(3) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 C11 1.527(3) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 C12 1.542(3) . ? C11 C16 1.548(3) . ? C11 H11A 0.9800 . ? C12 C13 1.519(3) . ? C12 H12A 0.9800 . ? C13 C14 1.551(3) . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C14 C15 1.529(3) . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C15 C21 1.516(3) . ? C15 C16 1.537(3) . ? C15 C19 1.555(3) . ? C16 C17 1.508(3) . ? C16 H16A 0.9800 . ? C17 C18 1.571(3) . ? C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? C18 C19 1.548(3) . ? C18 H18A 0.9700 . ? C18 H18B 0.9700 . ? C19 C22 1.558(3) . ? C19 H19A 0.9800 . ? C20 H20A 0.9600 . ? C20 H20B 0.9600 . ? C20 H20C 0.9600 . ? C21 H21A 0.9600 . ? C21 H21B 0.9600 . ? C21 H21C 0.9600 . ? C22 C23 1.530(3) . ? C22 C24 1.548(3) . ? C22 H22A 0.9800 . ? C23 H23A 0.9600 . ? C23 H23B 0.9600 . ? C23 H23C 0.9600 . ? C24 C25 1.538(3) . ? C24 H24A 0.9700 . ? C24 H24B 0.9700 . ? C25 C26 1.483(4) . ? C25 H25A 0.9700 . ? C25 H25B 0.9700 . ? C27 C28 1.454(4) . ? C27 H27A 0.9700 . ? C27 H27B 0.9700 . ? C28 C29 1.132(5) . ? C29 H29A 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 O2 C4 118.14(19) . . ? C26 O4 C27 114.9(2) . . ? N2 N1 C1 111.8(2) . . ? N3 N2 N1 171.3(4) . . ? C2 C1 N1 111.4(2) . . ? C2 C1 H1A 109.4 . . ? N1 C1 H1A 109.4 . . ? C2 C1 H1B 109.4 . . ? N1 C1 H1B 109.4 . . ? H1A C1 H1B 108.0 . . ? O1 C2 O2 124.3(2) . . ? O1 C2 C1 127.1(2) . . ? O2 C2 C1 108.5(2) . . ? C4 C3 C8 112.7(2) . . ? C4 C3 H3A 109.0 . . ? C8 C3 H3A 109.0 . . ? C4 C3 H3B 109.0 . . ? C8 C3 H3B 109.0 . . ? H3A C3 H3B 107.8 . . ? O2 C4 C3 104.9(2) . . ? O2 C4 C5 112.5(2) . . ? C3 C4 C5 112.25(19) . . ? O2 C4 H4A 109.0 . . ? C3 C4 H4A 109.0 . . ? C5 C4 H4A 109.0 . . ? C6 C5 C4 109.7(2) . . ? C6 C5 H5A 109.7 . . ? C4 C5 H5A 109.7 . . ? C6 C5 H5B 109.7 . . ? C4 C5 H5B 109.7 . . ? H5A C5 H5B 108.2 . . ? C5 C6 C7 114.5(2) . . ? C5 C6 H6A 108.6 . . ? C7 C6 H6A 108.6 . . ? C5 C6 H6B 108.6 . . ? C7 C6 H6B 108.6 . . ? H6A C6 H6B 107.6 . . ? C20 C7 C6 106.8(2) . . ? C20 C7 C8 109.5(2) . . ? C6 C7 C8 107.89(18) . . ? C20 C7 C12 111.84(19) . . ? C6 C7 C12 111.43(19) . . ? C8 C7 C12 109.29(19) . . ? C9 C8 C3 110.2(2) . . ? C9 C8 C7 112.32(19) . . ? C3 C8 C7 113.6(2) . . ? C9 C8 H8A 106.7 . . ? C3 C8 H8A 106.7 . . ? C7 C8 H8A 106.7 . . ? C8 C9 C10 111.9(2) . . ? C8 C9 H9A 109.2 . . ? C10 C9 H9A 109.2 . . ? C8 C9 H9B 109.2 . . ? C10 C9 H9B 109.2 . . ? H9A C9 H9B 107.9 . . ? C11 C10 C9 111.6(2) . . ? C11 C10 H10A 109.3 . . ? C9 C10 H10A 109.3 . . ? C11 C10 H10B 109.3 . . ? C9 C10 H10B 109.3 . . ? H10A C10 H10B 108.0 . . ? C10 C11 C12 110.83(17) . . ? C10 C11 C16 111.28(19) . . ? C12 C11 C16 108.77(17) . . ? C10 C11 H11A 108.6 . . ? C12 C11 H11A 108.6 . . ? C16 C11 H11A 108.6 . . ? C13 C12 C11 112.42(17) . . ? C13 C12 C7 113.28(19) . . ? C11 C12 C7 111.76(18) . . ? C13 C12 H12A 106.3 . . ? C11 C12 H12A 106.3 . . ? C7 C12 H12A 106.3 . . ? C12 C13 C14 113.5(2) . . ? C12 C13 H13A 108.9 . . ? C14 C13 H13A 108.9 . . ? C12 C13 H13B 108.9 . . ? C14 C13 H13B 108.9 . . ? H13A C13 H13B 107.7 . . ? C15 C14 C13 111.62(19) . . ? C15 C14 H14A 109.3 . . ? C13 C14 H14A 109.3 . . ? C15 C14 H14B 109.3 . . ? C13 C14 H14B 109.3 . . ? H14A C14 H14B 108.0 . . ? C21 C15 C14 111.2(2) . . ? C21 C15 C16 112.4(2) . . ? C14 C15 C16 107.23(17) . . ? C21 C15 C19 109.17(18) . . ? C14 C15 C19 116.73(19) . . ? C16 C15 C19 99.61(17) . . ? C17 C16 C15 105.89(17) . . ? C17 C16 C11 118.30(18) . . ? C15 C16 C11 113.23(18) . . ? C17 C16 H16A 106.2 . . ? C15 C16 H16A 106.2 . . ? C11 C16 H16A 106.2 . . ? C16 C17 C18 103.58(17) . . ? C16 C17 H17A 111.0 . . ? C18 C17 H17A 111.0 . . ? C16 C17 H17B 111.0 . . ? C18 C17 H17B 111.0 . . ? H17A C17 H17B 109.0 . . ? C19 C18 C17 106.20(18) . . ? C19 C18 H18A 110.5 . . ? C17 C18 H18A 110.5 . . ? C19 C18 H18B 110.5 . . ? C17 C18 H18B 110.5 . . ? H18A C18 H18B 108.7 . . ? C18 C19 C15 104.01(18) . . ? C18 C19 C22 112.75(18) . . ? C15 C19 C22 118.88(19) . . ? C18 C19 H19A 106.8 . . ? C15 C19 H19A 106.8 . . ? C22 C19 H19A 106.8 . . ? C7 C20 H20A 109.5 . . ? C7 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C7 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C15 C21 H21A 109.5 . . ? C15 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C15 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C23 C22 C24 112.4(2) . . ? C23 C22 C19 111.44(19) . . ? C24 C22 C19 109.86(19) . . ? C23 C22 H22A 107.6 . . ? C24 C22 H22A 107.6 . . ? C19 C22 H22A 107.6 . . ? C22 C23 H23A 109.5 . . ? C22 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C22 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C25 C24 C22 114.4(2) . . ? C25 C24 H24A 108.7 . . ? C22 C24 H24A 108.7 . . ? C25 C24 H24B 108.7 . . ? C22 C24 H24B 108.7 . . ? H24A C24 H24B 107.6 . . ? C26 C25 C24 112.6(2) . . ? C26 C25 H25A 109.1 . . ? C24 C25 H25A 109.1 . . ? C26 C25 H25B 109.1 . . ? C24 C25 H25B 109.1 . . ? H25A C25 H25B 107.8 . . ? O3 C26 O4 122.0(2) . . ? O3 C26 C25 128.9(2) . . ? O4 C26 C25 109.0(2) . . ? O4 C27 C28 107.9(3) . . ? O4 C27 H27A 110.1 . . ? C28 C27 H27A 110.1 . . ? O4 C27 H27B 110.1 . . ? C28 C27 H27B 110.1 . . ? H27A C27 H27B 108.4 . . ? C29 C28 C27 176.9(4) . . ? C28 C29 H29A 180.0 . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.52 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.167 _refine_diff_density_min -0.198 _refine_diff_density_rms 0.044