# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2011 data_global _journal_coden_Cambridge 182 _journal_volume ? _journal_page_first ? _journal_year ? loop_ _publ_author_name 'Jana, Poulami' 'Maity, Sibaprasad' 'Maity, Suman' 'Haldar, Debasish' _publ_contact_author_name 'HALDAR, DEBASISH' _publ_contact_author_email deba_h76@yahoo.com _publ_section_title ; A new peptide motif in the formation of supramolecular double helices ; # Attachment '- YUA.cif' data_YUA _database_code_depnum_ccdc_archive 'CCDC 797096' #TrackingRef '- YUA.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C29 H40 N3 O8' _chemical_formula_weight 558.64 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 ? _symmetry_space_group_name_H-M ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z' _cell_length_a 27.2619(12) _cell_length_b 8.1375(4) _cell_length_c 13.4148(6) _cell_angle_alpha 90.00 _cell_angle_beta 115.991(2) _cell_angle_gamma 90.00 _cell_volume 2675.0(2) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.387 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1196 _exptl_absorpt_coefficient_mu 0.101 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 26153 _diffrn_reflns_av_R_equivalents 0.0522 _diffrn_reflns_av_sigmaI/netI 0.0396 _diffrn_reflns_limit_h_min -34 _diffrn_reflns_limit_h_max 34 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.66 _diffrn_reflns_theta_max 27.00 _reflns_number_total 5787 _reflns_number_gt 4397 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1698P)^2^+2.0119P] 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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -1.7(13) _refine_ls_number_reflns 5787 _refine_ls_number_parameters 327 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0678 _refine_ls_R_factor_gt 0.0461 _refine_ls_wR_factor_ref 0.1880 _refine_ls_wR_factor_gt 0.1407 _refine_ls_goodness_of_fit_ref 0.749 _refine_ls_restrained_S_all 0.749 _refine_ls_shift/su_max 11.250 _refine_ls_shift/su_mean 0.109 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 O4 O 0.08843(17) 1.1553(6) 0.0022(3) 0.1180(13) Uani 1 1 d . . . O1S O 0.97477(9) 0.4852(3) 0.7246(2) 0.0647(6) Uani 1 1 d . . . O2S O 0.0427(3) 0.5939(16) 0.0993(5) 0.256(6) Uani 1 1 d . . . O5 O 0.06378(17) 0.9139(6) 0.0397(3) 0.1122(12) Uani 1 1 d . . . O6 O 0.07143(13) 1.1862(3) 0.3542(2) 0.0755(7) Uani 1 1 d . . . O10 O 0.18837(8) 0.8562(3) 0.47243(18) 0.0573(5) Uani 1 1 d . . . N1 N 0.09008(10) 0.9992(3) 0.25286(19) 0.0511(5) Uani 1 1 d . . . H1 H 0.0920 0.8964 0.2400 0.061 Uiso 1 1 calc R . . N2 N 0.10231(8) 0.7578(3) 0.40345(17) 0.0398(4) Uani 1 1 d . . . H2 H 0.0821 0.6739 0.3731 0.048 Uiso 1 1 calc R . . N3 N 0.21378(8) 0.5596(3) 0.38909(17) 0.0470(5) Uani 1 1 d . . . H3 H 0.2459 0.5205 0.4277 0.056 Uiso 1 1 calc R . . C1 C 0.0733(3) 1.1034(14) -0.1101(4) 0.149(3) Uani 1 1 d . . . H1A H 0.0912 1.0017 -0.1095 0.224 Uiso 1 1 calc R . . H1B H 0.0840 1.1857 -0.1479 0.224 Uiso 1 1 calc R . . H1C H 0.0345 1.0881 -0.1477 0.224 Uiso 1 1 calc R . . C2 C 0.08071(13) 1.0501(6) 0.0682(3) 0.0714(10) Uani 1 1 d . . . C3 C 0.09793(13) 1.1203(4) 0.1817(3) 0.0604(7) Uani 1 1 d . . . H3A H 0.0746 1.2152 0.1756 0.072 Uiso 1 1 calc R . . C4 C 0.08003(11) 1.0439(3) 0.3374(2) 0.0477(6) Uani 1 1 d . . . C5 C 0.07540(10) 0.9081(3) 0.4124(2) 0.0460(6) Uani 1 1 d . . . C6 C 0.15672(9) 0.7409(3) 0.4393(2) 0.0404(5) Uani 1 1 d . . . C7 C 0.17492(9) 0.5656(3) 0.43546(19) 0.0423(5) Uani 1 1 d . . . H7 H 0.1430 0.4988 0.3898 0.051 Uiso 1 1 calc R . . C8 C 0.20176(12) 0.4954(5) 0.5532(2) 0.0615(8) Uani 1 1 d . . . H8A H 0.2079 0.3788 0.5490 0.074 Uiso 1 1 calc R . . H8B H 0.2371 0.5474 0.5936 0.074 Uiso 1 1 calc R . . C9 C 0.16852(11) 0.5193(4) 0.6176(2) 0.0505(6) Uani 1 1 d . . . C10 C 0.11989(13) 0.4324(4) 0.5897(2) 0.0580(7) Uani 1 1 d . . . H10 H 0.1078 0.3589 0.5306 0.070 Uiso 1 1 calc R . . C11 C 0.08965(12) 0.4541(4) 0.6485(2) 0.0577(7) Uani 1 1 d . . . H11 H 0.0573 0.3964 0.6285 0.069 Uiso 1 1 calc R . . C12 C 0.10748(11) 0.5613(4) 0.7369(2) 0.0502(6) Uani 1 1 d . . . O3 O 0.08018(9) 0.5852(4) 0.80036(18) 0.0694(6) Uani 1 1 d . . . H3B H 0.0484 0.5558 0.7656 0.104 Uiso 1 1 calc R . . C14 C 0.19989(10) 0.6144(4) 0.2864(2) 0.0482(6) Uani 1 1 d . . . O1 O 0.24165(7) 0.6023(3) 0.25978(15) 0.0595(6) Uani 1 1 d . . . C16 C 0.23498(12) 0.6355(4) 0.1463(2) 0.0523(6) Uani 1 1 d . . . C17 C 0.21366(18) 0.8058(5) 0.1089(3) 0.0734(10) Uani 1 1 d . . . H17A H 0.1756 0.8100 0.0916 0.110 Uiso 1 1 calc R . . H17B H 0.2184 0.8336 0.0441 0.110 Uiso 1 1 calc R . . H17C H 0.2334 0.8827 0.1671 0.110 Uiso 1 1 calc R . . C18 C 0.29360(15) 0.6222(6) 0.1615(3) 0.0785(11) Uani 1 1 d . . . H18A H 0.3155 0.7054 0.2122 0.118 Uiso 1 1 calc R . . H18B H 0.2944 0.6370 0.0912 0.118 Uiso 1 1 calc R . . H18C H 0.3079 0.5157 0.1906 0.118 Uiso 1 1 calc R . . C19 C 0.19958(18) 0.5033(5) 0.0700(3) 0.0764(10) Uani 1 1 d . . . H19A H 0.2129 0.3974 0.1019 0.115 Uiso 1 1 calc R . . H19B H 0.2006 0.5115 -0.0005 0.115 Uiso 1 1 calc R . . H19C H 0.1627 0.5167 0.0600 0.115 Uiso 1 1 calc R . . O2 O 0.15503(8) 0.6715(3) 0.22707(17) 0.0633(6) Uani 1 1 d . . . C21 C 0.18462(11) 0.6276(5) 0.7049(2) 0.0574(7) Uani 1 1 d . . . H21 H 0.2164 0.6883 0.7244 0.069 Uiso 1 1 calc R . . C22 C 0.15456(12) 0.6481(4) 0.7643(2) 0.0556(7) Uani 1 1 d . . . H22 H 0.1664 0.7215 0.8234 0.067 Uiso 1 1 calc R . . C23 C 0.01482(12) 0.8675(5) 0.3682(3) 0.0634(8) Uani 1 1 d . . . H23A H 0.0008 0.8333 0.2922 0.095 Uiso 1 1 calc R . . H23B H -0.0046 0.9632 0.3730 0.095 Uiso 1 1 calc R . . H23C H 0.0101 0.7805 0.4116 0.095 Uiso 1 1 calc R . . C24 C 0.09808(15) 0.9679(4) 0.5318(3) 0.0626(8) Uani 1 1 d . . . H24A H 0.0941 0.8830 0.5774 0.094 Uiso 1 1 calc R . . H24B H 0.0784 1.0639 0.5352 0.094 Uiso 1 1 calc R . . H24C H 0.1360 0.9946 0.5580 0.094 Uiso 1 1 calc R . . C25 C 0.15653(19) 1.1780(6) 0.2316(4) 0.0895(13) Uani 1 1 d . . . H25A H 0.1660 1.2238 0.3037 0.134 Uiso 1 1 calc R . . H25B H 0.1607 1.2602 0.1846 0.134 Uiso 1 1 calc R . . H25C H 0.1800 1.0866 0.2381 0.134 Uiso 1 1 calc R . . H80 H 0.0471(11) 0.493(3) 0.107(2) 0.024(6) Uiso 1 1 d . . . H81 H 0.962(2) 0.388(8) 0.710(4) 0.102(16) Uiso 1 1 d . . . H83 H 0.971(2) 0.513(8) 0.809(4) 0.120(17) Uiso 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 O4 0.151(3) 0.150(3) 0.0709(17) 0.029(2) 0.0644(19) -0.012(3) O1S 0.0623(12) 0.0528(12) 0.0804(15) 0.0011(11) 0.0324(11) -0.0074(10) O2S 0.235(7) 0.409(15) 0.131(4) -0.053(7) 0.086(5) -0.198(10) O5 0.132(3) 0.138(3) 0.0626(17) -0.0131(19) 0.0391(17) -0.027(3) O6 0.125(2) 0.0414(12) 0.0743(14) 0.0057(10) 0.0571(15) 0.0181(12) O10 0.0490(10) 0.0626(13) 0.0631(12) -0.0111(10) 0.0272(9) -0.0163(9) N1 0.0687(13) 0.0411(11) 0.0525(12) 0.0049(10) 0.0347(11) 0.0028(10) N2 0.0395(9) 0.0381(11) 0.0463(10) -0.0007(9) 0.0228(8) -0.0008(8) N3 0.0431(9) 0.0646(14) 0.0381(10) 0.0086(10) 0.0223(8) 0.0137(10) C1 0.132(4) 0.261(10) 0.060(2) 0.033(4) 0.047(3) 0.008(6) C2 0.0542(14) 0.106(3) 0.0528(16) 0.0192(19) 0.0225(13) 0.0058(19) C3 0.0754(18) 0.0534(17) 0.0630(17) 0.0172(14) 0.0402(14) 0.0085(15) C4 0.0578(13) 0.0397(14) 0.0504(13) -0.0004(11) 0.0282(11) 0.0034(11) C5 0.0508(12) 0.0427(13) 0.0536(14) 0.0011(11) 0.0314(11) 0.0039(11) C6 0.0404(11) 0.0476(13) 0.0379(11) -0.0007(10) 0.0216(9) -0.0021(10) C7 0.0409(10) 0.0511(14) 0.0394(11) 0.0056(11) 0.0217(9) 0.0082(11) C8 0.0595(15) 0.084(2) 0.0502(15) 0.0197(15) 0.0324(12) 0.0280(15) C9 0.0556(13) 0.0591(17) 0.0409(13) 0.0120(11) 0.0250(11) 0.0143(12) C10 0.0746(18) 0.0562(17) 0.0498(14) -0.0043(13) 0.0335(13) -0.0024(15) C11 0.0630(16) 0.0603(18) 0.0566(16) -0.0018(14) 0.0325(13) -0.0110(14) C12 0.0509(12) 0.0600(16) 0.0434(12) 0.0046(12) 0.0239(10) 0.0053(13) O3 0.0641(11) 0.0986(19) 0.0592(11) -0.0079(12) 0.0398(10) -0.0014(13) C14 0.0472(12) 0.0621(16) 0.0392(11) 0.0003(11) 0.0225(10) 0.0059(12) O1 0.0537(10) 0.0923(17) 0.0414(9) 0.0061(10) 0.0290(8) 0.0113(10) C16 0.0653(15) 0.0620(17) 0.0402(12) -0.0004(12) 0.0328(11) -0.0013(13) C17 0.096(3) 0.063(2) 0.076(2) 0.0051(17) 0.052(2) 0.0060(18) C18 0.081(2) 0.104(3) 0.076(2) 0.010(2) 0.0570(18) 0.009(2) C19 0.105(3) 0.076(2) 0.0576(18) -0.0066(17) 0.0449(19) -0.017(2) O2 0.0499(10) 0.0924(17) 0.0476(10) 0.0166(11) 0.0214(8) 0.0173(11) C21 0.0478(13) 0.081(2) 0.0440(13) 0.0073(14) 0.0211(11) -0.0039(14) C22 0.0579(14) 0.0664(18) 0.0439(13) -0.0027(13) 0.0238(11) -0.0034(14) C23 0.0531(14) 0.0599(17) 0.092(2) 0.0052(17) 0.0459(16) 0.0082(14) C24 0.093(2) 0.0575(17) 0.0530(15) 0.0000(13) 0.0461(15) 0.0100(16) C25 0.102(3) 0.094(3) 0.079(2) -0.005(2) 0.047(2) -0.041(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 O4 C2 1.313(5) . ? O4 C1 1.440(7) . ? O1S H81 0.85(6) . ? O1S H83 1.20(6) . ? O2S H80 0.83(3) . ? O5 C2 1.197(6) . ? O6 C4 1.222(4) . ? O10 C6 1.219(3) . ? N1 C4 1.329(4) . ? N1 C3 1.452(4) . ? N1 H1 0.8600 . ? N2 C6 1.351(3) . ? N2 C5 1.458(3) . ? N2 H2 0.8600 . ? N3 C14 1.335(3) . ? N3 C7 1.445(3) . ? N3 H3 0.8600 . ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? C2 C3 1.496(5) . ? C3 C25 1.511(5) . ? C3 H3A 0.9800 . ? C4 C5 1.536(4) . ? C5 C24 1.522(4) . ? C5 C23 1.526(4) . ? C6 C7 1.519(4) . ? C7 C8 1.531(4) . ? C7 H7 0.9800 . ? C8 C9 1.513(4) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 C21 1.375(4) . ? C9 C10 1.401(4) . ? C10 C11 1.379(4) . ? C10 H10 0.9300 . ? C11 C12 1.378(4) . ? C11 H11 0.9300 . ? C12 C22 1.367(4) . ? C12 O3 1.368(3) . ? O3 H3B 0.8200 . ? C14 O2 1.221(3) . ? C14 O1 1.338(3) . ? O1 C16 1.477(3) . ? C16 C17 1.501(5) . ? C16 C19 1.507(5) . ? C16 C18 1.524(4) . ? 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 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? C21 C22 1.380(4) . ? C21 H21 0.9300 . ? C22 H22 0.9300 . ? C23 H23A 0.9600 . ? C23 H23B 0.9600 . ? C23 H23C 0.9600 . ? C24 H24A 0.9600 . ? C24 H24B 0.9600 . ? C24 H24C 0.9600 . ? C25 H25A 0.9600 . ? C25 H25B 0.9600 . ? C25 H25C 0.9600 . ? 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 O4 C1 117.2(6) . . ? H81 O1S H83 102(4) . . ? C4 N1 C3 121.4(3) . . ? C4 N1 H1 119.3 . . ? C3 N1 H1 119.3 . . ? C6 N2 C5 124.7(2) . . ? C6 N2 H2 117.6 . . ? C5 N2 H2 117.6 . . ? C14 N3 C7 120.2(2) . . ? C14 N3 H3 119.9 . . ? C7 N3 H3 119.9 . . ? O4 C1 H1A 109.4 . . ? O4 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? O4 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? O5 C2 O4 122.8(4) . . ? O5 C2 C3 125.7(3) . . ? O4 C2 C3 111.4(4) . . ? N1 C3 C2 109.8(3) . . ? N1 C3 C25 110.6(3) . . ? C2 C3 C25 111.6(3) . . ? N1 C3 H3A 108.2 . . ? C2 C3 H3A 108.2 . . ? C25 C3 H3A 108.2 . . ? O6 C4 N1 123.0(3) . . ? O6 C4 C5 118.9(3) . . ? N1 C4 C5 118.0(2) . . ? N2 C5 C24 111.6(2) . . ? N2 C5 C23 106.5(2) . . ? C24 C5 C23 110.5(2) . . ? N2 C5 C4 111.1(2) . . ? C24 C5 C4 110.3(2) . . ? C23 C5 C4 106.7(2) . . ? O10 C6 N2 122.9(2) . . ? O10 C6 C7 123.1(2) . . ? N2 C6 C7 114.1(2) . . ? N3 C7 C6 111.0(2) . . ? N3 C7 C8 108.81(19) . . ? C6 C7 C8 109.3(2) . . ? N3 C7 H7 109.2 . . ? C6 C7 H7 109.2 . . ? C8 C7 H7 109.2 . . ? C9 C8 C7 114.0(2) . . ? C9 C8 H8A 108.8 . . ? C7 C8 H8A 108.8 . . ? C9 C8 H8B 108.8 . . ? C7 C8 H8B 108.8 . . ? H8A C8 H8B 107.7 . . ? C21 C9 C10 117.6(3) . . ? C21 C9 C8 121.4(3) . . ? C10 C9 C8 121.1(3) . . ? C11 C10 C9 121.0(3) . . ? C11 C10 H10 119.5 . . ? C9 C10 H10 119.5 . . ? C12 C11 C10 120.0(3) . . ? C12 C11 H11 120.0 . . ? C10 C11 H11 120.0 . . ? C22 C12 O3 117.5(3) . . ? C22 C12 C11 119.6(3) . . ? O3 C12 C11 122.9(3) . . ? C12 O3 H3B 109.5 . . ? O2 C14 N3 123.4(2) . . ? O2 C14 O1 125.4(2) . . ? N3 C14 O1 111.2(2) . . ? C14 O1 C16 121.8(2) . . ? O1 C16 C17 111.6(3) . . ? O1 C16 C19 108.8(3) . . ? C17 C16 C19 113.2(3) . . ? O1 C16 C18 101.6(2) . . ? C17 C16 C18 109.9(3) . . ? C19 C16 C18 111.2(3) . . ? C16 C17 H17A 109.5 . . ? C16 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C16 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C16 C18 H18A 109.5 . . ? C16 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C16 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C16 C19 H19A 109.5 . . ? C16 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C16 C19 H19C 109.4 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C9 C21 C22 121.4(3) . . ? C9 C21 H21 119.3 . . ? C22 C21 H21 119.3 . . ? C12 C22 C21 120.5(3) . . ? C12 C22 H22 119.8 . . ? C21 C22 H22 119.7 . . ? C5 C23 H23A 109.5 . . ? C5 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C5 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C5 C24 H24A 109.5 . . ? C5 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C5 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C3 C25 H25A 109.5 . . ? C3 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? C3 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.534 _refine_diff_density_min -0.194 _refine_diff_density_rms 0.037 # Attachment '- YUI.cif' data_YUI _database_code_depnum_ccdc_archive 'CCDC 797097' #TrackingRef '- YUI.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C25 H38 N3 O7' _chemical_formula_weight 492.58 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 ? _symmetry_space_group_name_H-M ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x+1/2, -y, z+1/2' _cell_length_a 10.7245(5) _cell_length_b 14.2333(10) _cell_length_c 18.2023(9) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2778.5(3) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.178 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1060 _exptl_absorpt_coefficient_mu 0.086 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15047 _diffrn_reflns_av_R_equivalents 0.0434 _diffrn_reflns_av_sigmaI/netI 0.0525 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.63 _diffrn_reflns_theta_max 26.99 _reflns_number_total 5905 _reflns_number_gt 4251 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1026P)^2^+0.7786P] 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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 1.7(12) _refine_ls_number_reflns 5905 _refine_ls_number_parameters 325 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0700 _refine_ls_R_factor_gt 0.0409 _refine_ls_wR_factor_ref 0.1428 _refine_ls_wR_factor_gt 0.1087 _refine_ls_goodness_of_fit_ref 0.793 _refine_ls_restrained_S_all 0.793 _refine_ls_shift/su_max 0.316 _refine_ls_shift/su_mean 0.032 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 O3 O 0.9215(3) -0.14479(14) 0.22315(13) 0.0847(8) Uani 1 1 d . . . H16 H 0.9741 -0.1558 0.2547 0.127 Uiso 1 1 calc R . . O4 O 0.95165(15) 0.32677(12) 0.15152(9) 0.0467(4) Uani 1 1 d . . . O5 O 1.09091(15) 0.32887(13) -0.04691(10) 0.0520(4) Uani 1 1 d . . . O6 O 0.8879(2) 0.59186(17) -0.13531(11) 0.0765(6) Uani 1 1 d . . . O1 O 0.67144(19) 0.53744(11) 0.20926(10) 0.0562(5) Uani 1 1 d . . . C2 C 0.5123(3) 0.6130(2) 0.1348(2) 0.0731(9) Uani 1 1 d . . . H9 H 0.5290 0.5768 0.0914 0.110 Uiso 1 1 calc R . . H7 H 0.4783 0.6728 0.1212 0.110 Uiso 1 1 calc R . . H8 H 0.4535 0.5800 0.1651 0.110 Uiso 1 1 calc R . . O2 O 0.7072(2) 0.46058(12) 0.10132(9) 0.0563(5) Uani 1 1 d . . . N3 N 0.92639(18) 0.41097(13) -0.00692(10) 0.0390(4) Uani 1 1 d . . . H26 H 0.8564 0.4089 0.0161 0.047 Uiso 1 1 calc R . . N2 N 0.83166(17) 0.25747(12) 0.06602(9) 0.0331(4) Uani 1 1 d . . . H19 H 0.7566 0.2424 0.0543 0.040 Uiso 1 1 calc R . . O7 O 0.75577(18) 0.53251(15) -0.05313(11) 0.0656(6) Uani 1 1 d . . . C25 C 1.2482(4) 0.5503(3) 0.0032(2) 0.0945(12) Uani 1 1 d . . . H39 H 1.2342 0.5151 -0.0410 0.142 Uiso 1 1 calc R . . H38 H 1.3247 0.5301 0.0256 0.142 Uiso 1 1 calc R . . H37 H 1.2535 0.6160 -0.0084 0.142 Uiso 1 1 calc R . . C24 C 1.1411(3) 0.5340(2) 0.05595(18) 0.0698(8) Uani 1 1 d . . . H35 H 1.1589 0.5670 0.1014 0.084 Uiso 1 1 calc R . . H36 H 1.1369 0.4675 0.0672 0.084 Uiso 1 1 calc R . . C22 C 1.0136(3) 0.56580(19) 0.02791(15) 0.0538(7) Uani 1 1 d . . . H31 H 0.9548 0.5573 0.0685 0.065 Uiso 1 1 calc R . . C19 C 0.9688(2) 0.50085(16) -0.03563(13) 0.0432(5) Uani 1 1 d . . . H27 H 1.0404 0.4888 -0.0677 0.052 Uiso 1 1 calc R . . C18 C 0.9910(2) 0.33179(16) -0.01460(12) 0.0355(5) Uani 1 1 d . . . C15 C 0.9296(2) 0.24016(15) 0.01206(12) 0.0374(5) Uani 1 1 d . . . C14 C 0.85015(19) 0.29481(14) 0.13213(11) 0.0323(4) Uani 1 1 d . . . C6 C 0.7384(2) 0.29370(15) 0.18359(11) 0.0361(5) Uani 1 1 d . . . H11 H 0.6654 0.2683 0.1580 0.043 Uiso 1 1 calc R . . C7 C 0.7679(2) 0.23321(16) 0.25125(12) 0.0422(5) Uani 1 1 d . . . H12 H 0.8318 0.2649 0.2797 0.051 Uiso 1 1 calc R . . H13 H 0.6936 0.2301 0.2815 0.051 Uiso 1 1 calc R . . C8 C 0.8113(2) 0.13428(15) 0.23641(12) 0.0389(5) Uani 1 1 d . . . C9 C 0.7335(3) 0.06618(19) 0.20782(16) 0.0563(7) Uani 1 1 d . . . H18 H 0.6542 0.0828 0.1918 0.068 Uiso 1 1 calc R . . C10 C 0.7717(3) -0.02652(19) 0.20269(17) 0.0632(8) Uani 1 1 d . . . H17 H 0.7183 -0.0714 0.1831 0.076 Uiso 1 1 calc R . . C11 C 0.8881(3) -0.05236(19) 0.22646(13) 0.0555(7) Uani 1 1 d . . . C13 C 0.9290(3) 0.10715(19) 0.25682(15) 0.0531(6) Uani 1 1 d . . . H14 H 0.9841 0.1523 0.2745 0.064 Uiso 1 1 calc R . . C12 C 0.9682(3) 0.0150(2) 0.25203(17) 0.0597(7) Uani 1 1 d . . . H15 H 1.0488 -0.0012 0.2661 0.072 Uiso 1 1 calc R . . C16 C 1.0268(3) 0.1729(2) 0.04291(17) 0.0595(7) Uani 1 1 d . . . H21 H 1.0684 0.2020 0.0837 0.089 Uiso 1 1 calc R . . H22 H 1.0867 0.1582 0.0054 0.089 Uiso 1 1 calc R . . H20 H 0.9867 0.1163 0.0590 0.089 Uiso 1 1 calc R . . C23 C 1.0117(4) 0.6692(2) 0.0085(2) 0.0793(10) Uani 1 1 d . . . H33 H 1.0472 0.7049 0.0481 0.119 Uiso 1 1 calc R . . H34 H 0.9272 0.6890 0.0005 0.119 Uiso 1 1 calc R . . H32 H 1.0594 0.6794 -0.0354 0.119 Uiso 1 1 calc R . . C20 C 0.8681(3) 0.54581(18) -0.08165(13) 0.0495(6) Uani 1 1 d . . . C21 C 0.6514(3) 0.5751(3) -0.0900(2) 0.0918(12) Uani 1 1 d . . . H30 H 0.6651 0.6415 -0.0943 0.138 Uiso 1 1 calc R . . H28 H 0.5768 0.5639 -0.0622 0.138 Uiso 1 1 calc R . . H29 H 0.6427 0.5482 -0.1381 0.138 Uiso 1 1 calc R . . C17 C 0.8677(3) 0.1979(2) -0.05594(15) 0.0625(8) Uani 1 1 d . . . H25 H 0.8244 0.1414 -0.0425 0.094 Uiso 1 1 calc R . . H23 H 0.9302 0.1835 -0.0920 0.094 Uiso 1 1 calc R . . H24 H 0.8094 0.2422 -0.0761 0.094 Uiso 1 1 calc R . . N1 N 0.7109(2) 0.38709(13) 0.21111(11) 0.0474(5) Uani 1 1 d . . . H10 H 0.7039 0.3947 0.2578 0.057 Uiso 1 1 calc R . . C5 C 0.6960(2) 0.46183(16) 0.16765(13) 0.0429(5) Uani 1 1 d . . . C1 C 0.6318(3) 0.62742(18) 0.17695(16) 0.0543(7) Uani 1 1 d . . . C3 C 0.6104(4) 0.6874(2) 0.24451(19) 0.0760(9) Uani 1 1 d . . . H6 H 0.5546 0.6555 0.2773 0.114 Uiso 1 1 calc R . . H5 H 0.5746 0.7464 0.2302 0.114 Uiso 1 1 calc R . . H4 H 0.6885 0.6983 0.2688 0.114 Uiso 1 1 calc R . . C4 C 0.7339(3) 0.6676(2) 0.1289(2) 0.0702(8) Uani 1 1 d . . . H2 H 0.8109 0.6684 0.1558 0.105 Uiso 1 1 calc R . . H3 H 0.7123 0.7305 0.1148 0.105 Uiso 1 1 calc R . . H1 H 0.7432 0.6294 0.0858 0.105 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 O3 0.126(2) 0.0513(11) 0.0765(14) -0.0148(10) -0.0453(14) 0.0363(12) O4 0.0415(9) 0.0524(9) 0.0461(9) -0.0029(8) -0.0051(7) -0.0124(8) O5 0.0403(9) 0.0516(10) 0.0643(11) 0.0052(9) 0.0207(8) 0.0050(8) O6 0.0882(16) 0.0889(15) 0.0525(11) 0.0337(11) -0.0015(11) 0.0018(13) O1 0.0833(14) 0.0397(9) 0.0456(9) -0.0063(8) -0.0006(9) 0.0151(9) C2 0.0587(18) 0.077(2) 0.084(2) -0.0014(18) -0.0040(17) 0.0156(16) O2 0.0809(13) 0.0483(10) 0.0396(9) 0.0023(7) 0.0044(9) 0.0156(9) N3 0.0374(10) 0.0373(10) 0.0423(10) 0.0070(8) 0.0098(8) 0.0037(8) N2 0.0288(9) 0.0369(9) 0.0336(9) -0.0032(7) 0.0014(7) -0.0020(7) O7 0.0509(11) 0.0807(14) 0.0652(12) 0.0332(11) 0.0002(10) 0.0123(10) C25 0.063(2) 0.117(3) 0.103(3) 0.000(3) -0.005(2) -0.013(2) C24 0.073(2) 0.076(2) 0.0598(17) -0.0010(16) -0.0123(16) -0.0084(17) C22 0.0602(17) 0.0486(14) 0.0525(15) 0.0032(11) 0.0075(13) -0.0064(12) C19 0.0472(14) 0.0402(12) 0.0423(12) 0.0091(10) 0.0082(10) 0.0018(10) C18 0.0309(11) 0.0411(11) 0.0345(10) -0.0004(9) 0.0038(9) 0.0033(9) C15 0.0363(12) 0.0346(10) 0.0413(11) -0.0033(9) 0.0075(10) 0.0022(9) C14 0.0327(11) 0.0312(9) 0.0331(10) 0.0015(8) -0.0035(9) -0.0014(9) C6 0.0403(12) 0.0363(10) 0.0318(10) -0.0015(8) 0.0020(9) 0.0016(9) C7 0.0535(14) 0.0439(12) 0.0291(10) -0.0007(9) 0.0052(10) 0.0028(10) C8 0.0481(13) 0.0393(10) 0.0294(10) 0.0052(9) 0.0014(10) 0.0025(10) C9 0.0563(17) 0.0501(14) 0.0625(16) -0.0040(12) -0.0212(14) 0.0094(13) C10 0.078(2) 0.0470(14) 0.0644(17) -0.0090(12) -0.0315(16) 0.0064(14) C11 0.0758(19) 0.0496(14) 0.0413(13) -0.0035(11) -0.0142(13) 0.0187(13) C13 0.0505(14) 0.0508(14) 0.0581(15) 0.0041(12) -0.0081(13) -0.0002(11) C12 0.0506(16) 0.0620(16) 0.0664(17) 0.0017(14) -0.0148(14) 0.0166(13) C16 0.0550(16) 0.0444(13) 0.0792(19) 0.0136(13) 0.0222(14) 0.0186(13) C23 0.093(2) 0.0525(17) 0.092(2) -0.0021(17) -0.002(2) -0.0080(18) C20 0.0632(17) 0.0466(13) 0.0388(12) 0.0097(11) -0.0012(12) 0.0037(12) C21 0.064(2) 0.110(3) 0.101(3) 0.040(2) -0.013(2) 0.020(2) C17 0.0710(19) 0.0688(18) 0.0477(14) -0.0224(13) 0.0165(14) -0.0165(15) N1 0.0698(14) 0.0401(10) 0.0323(9) -0.0017(8) 0.0048(9) 0.0132(9) C5 0.0450(13) 0.0434(12) 0.0402(12) -0.0041(10) 0.0010(10) 0.0048(11) C1 0.0552(16) 0.0406(13) 0.0670(17) -0.0021(12) 0.0018(14) 0.0112(12) C3 0.089(2) 0.0519(17) 0.087(2) -0.0216(16) 0.005(2) 0.0100(16) C4 0.0680(19) 0.0539(16) 0.089(2) 0.0081(16) 0.0074(17) 0.0020(15) _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 O3 C11 1.365(3) . ? O3 H16 0.8200 . ? O4 C14 1.231(3) . ? O5 C18 1.223(3) . ? O6 C20 1.195(3) . ? O1 C5 1.342(3) . ? O1 C1 1.472(3) . ? C2 C1 1.507(4) . ? C2 H9 0.9600 . ? C2 H7 0.9600 . ? C2 H8 0.9600 . ? O2 C5 1.213(3) . ? N3 C18 1.331(3) . ? N3 C19 1.455(3) . ? N3 H26 0.8600 . ? N2 C14 1.330(3) . ? N2 C15 1.459(3) . ? N2 H19 0.8600 . ? O7 C20 1.325(3) . ? O7 C21 1.439(4) . ? C25 C24 1.514(5) . ? C25 H39 0.9600 . ? C25 H38 0.9600 . ? C25 H37 0.9600 . ? C24 C22 1.527(4) . ? C24 H35 0.9700 . ? C24 H36 0.9700 . ? C22 C23 1.514(4) . ? C22 C19 1.557(4) . ? C22 H31 0.9800 . ? C19 C20 1.509(4) . ? C19 H27 0.9800 . ? C18 C15 1.540(3) . ? C15 C16 1.523(3) . ? C15 C17 1.528(4) . ? C14 C6 1.521(3) . ? C6 N1 1.451(3) . ? C6 C7 1.536(3) . ? C6 H11 0.9800 . ? C7 C8 1.507(3) . ? C7 H12 0.9700 . ? C7 H13 0.9700 . ? C8 C13 1.371(4) . ? C8 C9 1.381(4) . ? C9 C10 1.385(4) . ? C9 H18 0.9300 . ? C10 C11 1.371(4) . ? C10 H17 0.9300 . ? C11 C12 1.369(4) . ? C13 C12 1.380(4) . ? C13 H14 0.9300 . ? C12 H15 0.9300 . ? C16 H21 0.9600 . ? C16 H22 0.9600 . ? C16 H20 0.9600 . ? C23 H33 0.9600 . ? C23 H34 0.9600 . ? C23 H32 0.9600 . ? C21 H30 0.9600 . ? C21 H28 0.9600 . ? C21 H29 0.9600 . ? C17 H25 0.9600 . ? C17 H23 0.9600 . ? C17 H24 0.9600 . ? N1 C5 1.335(3) . ? N1 H10 0.8600 . ? C1 C4 1.513(4) . ? C1 C3 1.514(4) . ? C3 H6 0.9600 . ? C3 H5 0.9600 . ? C3 H4 0.9600 . ? C4 H2 0.9600 . ? C4 H3 0.9600 . ? C4 H1 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 C11 O3 H16 109.5 . . ? C5 O1 C1 121.9(2) . . ? C1 C2 H9 109.5 . . ? C1 C2 H7 109.5 . . ? H9 C2 H7 109.5 . . ? C1 C2 H8 109.5 . . ? H9 C2 H8 109.5 . . ? H7 C2 H8 109.5 . . ? C18 N3 C19 122.97(19) . . ? C18 N3 H26 118.5 . . ? C19 N3 H26 118.5 . . ? C14 N2 C15 124.69(18) . . ? C14 N2 H19 117.7 . . ? C15 N2 H19 117.7 . . ? C20 O7 C21 117.6(2) . . ? C24 C25 H39 109.5 . . ? C24 C25 H38 109.5 . . ? H39 C25 H38 109.5 . . ? C24 C25 H37 109.5 . . ? H39 C25 H37 109.5 . . ? H38 C25 H37 109.5 . . ? C25 C24 C22 114.9(3) . . ? C25 C24 H35 108.5 . . ? C22 C24 H35 108.5 . . ? C25 C24 H36 108.5 . . ? C22 C24 H36 108.5 . . ? H35 C24 H36 107.5 . . ? C23 C22 C24 112.2(3) . . ? C23 C22 C19 113.6(2) . . ? C24 C22 C19 110.4(2) . . ? C23 C22 H31 106.7 . . ? C24 C22 H31 106.7 . . ? C19 C22 H31 106.7 . . ? N3 C19 C20 110.4(2) . . ? N3 C19 C22 110.60(19) . . ? C20 C19 C22 112.4(2) . . ? N3 C19 H27 107.7 . . ? C20 C19 H27 107.7 . . ? C22 C19 H27 107.7 . . ? O5 C18 N3 122.4(2) . . ? O5 C18 C15 119.9(2) . . ? N3 C18 C15 117.47(18) . . ? N2 C15 C16 110.54(19) . . ? N2 C15 C17 107.41(19) . . ? C16 C15 C17 110.4(2) . . ? N2 C15 C18 112.17(17) . . ? C16 C15 C18 110.79(19) . . ? C17 C15 C18 105.33(19) . . ? O4 C14 N2 122.6(2) . . ? O4 C14 C6 121.60(19) . . ? N2 C14 C6 115.80(18) . . ? N1 C6 C14 111.29(18) . . ? N1 C6 C7 106.17(17) . . ? C14 C6 C7 109.70(18) . . ? N1 C6 H11 109.9 . . ? C14 C6 H11 109.9 . . ? C7 C6 H11 109.9 . . ? C8 C7 C6 116.34(18) . . ? C8 C7 H12 108.2 . . ? C6 C7 H12 108.2 . . ? C8 C7 H13 108.2 . . ? C6 C7 H13 108.2 . . ? H12 C7 H13 107.4 . . ? C13 C8 C9 117.4(2) . . ? C13 C8 C7 119.9(2) . . ? C9 C8 C7 122.4(2) . . ? C8 C9 C10 121.0(2) . . ? C8 C9 H18 119.5 . . ? C10 C9 H18 119.5 . . ? C11 C10 C9 120.3(3) . . ? C11 C10 H17 119.9 . . ? C9 C10 H17 119.9 . . ? O3 C11 C12 121.7(3) . . ? O3 C11 C10 118.9(3) . . ? C12 C11 C10 119.4(2) . . ? C8 C13 C12 122.1(3) . . ? C8 C13 H14 119.0 . . ? C12 C13 H14 119.0 . . ? C11 C12 C13 119.7(3) . . ? C11 C12 H15 120.1 . . ? C13 C12 H15 120.1 . . ? C15 C16 H21 109.5 . . ? C15 C16 H22 109.5 . . ? H21 C16 H22 109.5 . . ? C15 C16 H20 109.5 . . ? H21 C16 H20 109.5 . . ? H22 C16 H20 109.5 . . ? C22 C23 H33 109.5 . . ? C22 C23 H34 109.5 . . ? H33 C23 H34 109.5 . . ? C22 C23 H32 109.5 . . ? H33 C23 H32 109.5 . . ? H34 C23 H32 109.5 . . ? O6 C20 O7 124.1(3) . . ? O6 C20 C19 124.0(3) . . ? O7 C20 C19 111.86(19) . . ? O7 C21 H30 109.5 . . ? O7 C21 H28 109.5 . . ? H30 C21 H28 109.5 . . ? O7 C21 H29 109.5 . . ? H30 C21 H29 109.5 . . ? H28 C21 H29 109.5 . . ? C15 C17 H25 109.5 . . ? C15 C17 H23 109.5 . . ? H25 C17 H23 109.5 . . ? C15 C17 H24 109.5 . . ? H25 C17 H24 109.5 . . ? H23 C17 H24 109.5 . . ? C5 N1 C6 123.33(18) . . ? C5 N1 H10 118.3 . . ? C6 N1 H10 118.3 . . ? O2 C5 N1 124.5(2) . . ? O2 C5 O1 126.3(2) . . ? N1 C5 O1 109.1(2) . . ? O1 C1 C2 109.3(2) . . ? O1 C1 C4 110.5(2) . . ? C2 C1 C4 111.9(3) . . ? O1 C1 C3 102.1(2) . . ? C2 C1 C3 111.2(3) . . ? C4 C1 C3 111.4(3) . . ? C1 C3 H6 109.5 . . ? C1 C3 H5 109.5 . . ? H6 C3 H5 109.5 . . ? C1 C3 H4 109.5 . . ? H6 C3 H4 109.5 . . ? H5 C3 H4 109.5 . . ? C1 C4 H2 109.5 . . ? C1 C4 H3 109.5 . . ? H2 C4 H3 109.5 . . ? C1 C4 H1 109.5 . . ? H2 C4 H1 109.5 . . ? H3 C4 H1 109.5 . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 26.99 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.146 _refine_diff_density_min -0.189 _refine_diff_density_rms 0.040 # Attachment '- YUL.cif' data_YUL _database_code_depnum_ccdc_archive 'CCDC 797098' #TrackingRef '- YUL.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C25 H39 N3 O7' _chemical_formula_weight 493.59 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 ? _symmetry_space_group_name_H-M ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x+1/2, -y, z+1/2' _cell_length_a 10.6501(5) _cell_length_b 14.1442(5) _cell_length_c 18.3996(8) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2771.7(2) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.183 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1064 _exptl_absorpt_coefficient_mu 0.086 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 20889 _diffrn_reflns_av_R_equivalents 0.0499 _diffrn_reflns_av_sigmaI/netI 0.0320 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.82 _diffrn_reflns_theta_max 22.77 _reflns_number_total 3756 _reflns_number_gt 3351 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0867P)^2^+0.4298P] 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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.4(12) _refine_ls_number_reflns 3756 _refine_ls_number_parameters 325 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0443 _refine_ls_R_factor_gt 0.0366 _refine_ls_wR_factor_ref 0.1110 _refine_ls_wR_factor_gt 0.1002 _refine_ls_goodness_of_fit_ref 0.893 _refine_ls_restrained_S_all 0.893 _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 0.8920(2) 0.66242(13) 0.24755(13) 0.0912(8) Uani 1 1 d . . . H1 H 0.9464 0.6738 0.2778 0.137 Uiso 1 1 calc R . . O2 O 0.7305(2) -0.00418(19) -0.07853(13) 0.0981(8) Uani 1 1 d . . . O3 O 0.8661(3) -0.09641(17) -0.13333(12) 0.0926(7) Uani 1 1 d . . . O4 O 1.04988(16) 0.18608(14) -0.06088(10) 0.0654(5) Uani 1 1 d . . . O5 O 0.70197(18) 0.04773(12) 0.10070(9) 0.0604(5) Uani 1 1 d . . . O6 O 0.66034(19) -0.02767(12) 0.20752(9) 0.0647(5) Uani 1 1 d . . . O7 O 0.94872(16) 0.19440(12) 0.13946(9) 0.0548(4) Uani 1 1 d . . . N1 N 0.80479(16) 0.25330(12) 0.06272(9) 0.0381(4) Uani 1 1 d . . . H1A H 0.7263 0.2652 0.0566 0.046 Uiso 1 1 calc R . . N2 N 0.8955(2) 0.09989(13) -0.01364(11) 0.0512(5) Uani 1 1 d . . . H2 H 0.8287 0.0990 0.0126 0.061 Uiso 1 1 calc R . . N3 N 0.7149(2) 0.12082(13) 0.21008(10) 0.0537(5) Uani 1 1 d . . . H3 H 0.7152 0.1108 0.2562 0.064 Uiso 1 1 calc R . . C1 C 0.8689(3) 0.56799(17) 0.24625(15) 0.0598(7) Uani 1 1 d . . . C2 C 0.7660(3) 0.53507(19) 0.20988(18) 0.0768(9) Uani 1 1 d . . . H2A H 0.7136 0.5774 0.1859 0.092 Uiso 1 1 calc R . . C3 C 0.7390(3) 0.43953(18) 0.20836(17) 0.0688(8) Uani 1 1 d . . . H3A H 0.6683 0.4187 0.1834 0.083 Uiso 1 1 calc R . . C4 C 0.8143(2) 0.37448(16) 0.24296(11) 0.0438(6) Uani 1 1 d . . . C5 C 0.7810(3) 0.27177(16) 0.25195(12) 0.0499(6) Uani 1 1 d . . . H5A H 0.7147 0.2676 0.2879 0.060 Uiso 1 1 calc R . . H5B H 0.8538 0.2397 0.2719 0.060 Uiso 1 1 calc R . . C6 C 0.7388(2) 0.21708(15) 0.18499(11) 0.0419(5) Uani 1 1 d . . . H6 H 0.6612 0.2447 0.1658 0.050 Uiso 1 1 calc R . . C7 C 0.8405(2) 0.21934(14) 0.12701(11) 0.0384(5) Uani 1 1 d . . . C8 C 0.8897(2) 0.27175(16) 0.00169(13) 0.0459(6) Uani 1 1 d . . . C9 C 0.9536(2) 0.18114(17) -0.02442(12) 0.0438(5) Uani 1 1 d . . . C10 C 0.9408(3) 0.01225(17) -0.04459(13) 0.0529(6) Uani 1 1 d . . . H10 H 1.0112 0.0283 -0.0766 0.063 Uiso 1 1 calc R . . C11 C 0.9918(3) -0.0559(2) 0.01348(17) 0.0776(9) Uani 1 1 d . . . H11A H 1.0245 -0.0187 0.0535 0.093 Uiso 1 1 calc R . . H11B H 0.9222 -0.0929 0.0321 0.093 Uiso 1 1 calc R . . C12 C 1.0920(4) -0.1224(2) -0.01077(17) 0.0819(10) Uani 1 1 d . . . H12 H 1.0716 -0.1435 -0.0601 0.098 Uiso 1 1 calc R . . C13 C 1.1015(8) -0.2077(3) 0.0368(3) 0.168(3) Uani 1 1 d . . . H13A H 1.1274 -0.1889 0.0846 0.252 Uiso 1 1 calc R . . H13B H 1.1622 -0.2507 0.0168 0.252 Uiso 1 1 calc R . . H13C H 1.0212 -0.2382 0.0395 0.252 Uiso 1 1 calc R . . C14 C 0.6297(4) -0.0453(4) -0.1203(3) 0.141(2) Uani 1 1 d . . . H14A H 0.6175 -0.0094 -0.1640 0.211 Uiso 1 1 calc R . . H14B H 0.5538 -0.0444 -0.0921 0.211 Uiso 1 1 calc R . . H14C H 0.6505 -0.1093 -0.1325 0.211 Uiso 1 1 calc R . . C15 C 0.8430(3) -0.03477(19) -0.09071(13) 0.0593(7) Uani 1 1 d . . . C16 C 0.6924(2) 0.04699(17) 0.16640(14) 0.0497(6) Uani 1 1 d . . . C17 C 0.6211(3) -0.11779(18) 0.17592(16) 0.0634(7) Uani 1 1 d . . . C18 C 0.7255(3) -0.1603(2) 0.1319(2) 0.0916(11) Uani 1 1 d . . . H18A H 0.7350 -0.1258 0.0874 0.137 Uiso 1 1 calc R . . H18B H 0.7060 -0.2251 0.1212 0.137 Uiso 1 1 calc R . . H18C H 0.8024 -0.1574 0.1591 0.137 Uiso 1 1 calc R . . C19 C 0.5973(4) -0.1771(2) 0.24318(19) 0.0883(10) Uani 1 1 d . . . H19A H 0.6751 -0.1878 0.2682 0.132 Uiso 1 1 calc R . . H19B H 0.5613 -0.2366 0.2292 0.132 Uiso 1 1 calc R . . H19C H 0.5402 -0.1443 0.2748 0.132 Uiso 1 1 calc R . . C20 C 0.5030(3) -0.1034(3) 0.1325(2) 0.0930(11) Uani 1 1 d . . . H20A H 0.4438 -0.0679 0.1608 0.139 Uiso 1 1 calc R . . H20B H 0.4675 -0.1638 0.1203 0.139 Uiso 1 1 calc R . . H20C H 0.5224 -0.0695 0.0888 0.139 Uiso 1 1 calc R . . C21 C 0.9469(3) 0.5044(2) 0.27861(16) 0.0651(7) Uani 1 1 d . . . H21 H 1.0191 0.5252 0.3021 0.078 Uiso 1 1 calc R . . C22 C 0.9194(3) 0.40906(19) 0.27677(15) 0.0588(7) Uani 1 1 d . . . H22 H 0.9740 0.3669 0.2992 0.071 Uiso 1 1 calc R . . C23 C 0.9861(3) 0.34650(19) 0.02216(18) 0.0704(8) Uani 1 1 d . . . H23A H 0.9437 0.4041 0.0347 0.106 Uiso 1 1 calc R . . H23B H 1.0410 0.3577 -0.0183 0.106 Uiso 1 1 calc R . . H23C H 1.0343 0.3249 0.0630 0.106 Uiso 1 1 calc R . . C24 C 0.8085(3) 0.3059(2) -0.06210(14) 0.0688(8) Uani 1 1 d . . . H24A H 0.7507 0.2569 -0.0757 0.103 Uiso 1 1 calc R . . H24B H 0.8615 0.3208 -0.1027 0.103 Uiso 1 1 calc R . . H24C H 0.7626 0.3612 -0.0478 0.103 Uiso 1 1 calc R . . C25 C 1.2181(4) -0.0739(4) -0.0130(3) 0.149(2) Uani 1 1 d . . . H25A H 1.2401 -0.0529 0.0349 0.223 Uiso 1 1 calc R . . H25B H 1.2139 -0.0205 -0.0451 0.223 Uiso 1 1 calc R . . H25C H 1.2804 -0.1174 -0.0303 0.223 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 0.1196(19) 0.0473(11) 0.1066(17) 0.0135(11) -0.0565(15) -0.0258(12) O2 0.0665(13) 0.115(2) 0.1127(18) -0.0692(16) -0.0057(13) -0.0005(13) O3 0.1170(19) 0.0856(14) 0.0751(13) -0.0384(13) -0.0222(13) 0.0260(14) O4 0.0518(10) 0.0696(12) 0.0749(11) -0.0101(10) 0.0248(10) -0.0130(9) O5 0.0845(13) 0.0509(10) 0.0459(10) -0.0006(8) 0.0029(9) -0.0156(10) O6 0.0951(14) 0.0404(9) 0.0586(10) 0.0078(9) 0.0045(10) -0.0160(10) O7 0.0472(10) 0.0596(10) 0.0577(10) 0.0007(8) -0.0081(8) 0.0146(8) N1 0.0349(9) 0.0402(10) 0.0391(10) 0.0020(8) -0.0021(8) 0.0018(8) N2 0.0509(11) 0.0479(12) 0.0549(11) -0.0112(9) 0.0160(10) -0.0087(10) N3 0.0804(15) 0.0389(11) 0.0417(10) 0.0019(9) 0.0005(10) -0.0098(11) C1 0.0725(18) 0.0465(15) 0.0604(15) 0.0043(12) -0.0173(15) -0.0122(13) C2 0.086(2) 0.0443(15) 0.100(2) 0.0042(15) -0.0447(19) -0.0026(15) C3 0.0708(19) 0.0483(15) 0.0874(19) 0.0052(14) -0.0342(17) -0.0077(14) C4 0.0499(14) 0.0425(13) 0.0391(12) 0.0007(10) 0.0002(11) -0.0029(11) C5 0.0655(15) 0.0433(13) 0.0410(12) 0.0004(10) 0.0024(11) 0.0015(12) C6 0.0481(13) 0.0372(12) 0.0404(11) 0.0031(9) -0.0012(10) 0.0013(10) C7 0.0404(13) 0.0310(11) 0.0439(13) -0.0033(9) -0.0030(10) 0.0007(10) C8 0.0434(12) 0.0456(14) 0.0488(12) 0.0012(11) 0.0087(11) -0.0080(11) C9 0.0388(12) 0.0497(14) 0.0429(12) -0.0034(10) 0.0034(11) -0.0087(11) C10 0.0625(15) 0.0467(13) 0.0494(13) -0.0070(11) 0.0124(12) 0.0033(12) C11 0.089(2) 0.087(2) 0.0568(16) -0.0011(15) 0.0074(16) 0.0221(18) C12 0.105(3) 0.076(2) 0.0646(18) -0.0088(16) -0.0051(18) 0.0311(19) C13 0.275(8) 0.121(4) 0.109(3) 0.014(3) 0.025(4) 0.100(5) C14 0.081(2) 0.166(4) 0.176(4) -0.106(4) -0.028(3) 0.004(3) C15 0.083(2) 0.0485(15) 0.0469(14) -0.0103(13) 0.0022(13) 0.0030(15) C16 0.0530(15) 0.0406(13) 0.0557(16) 0.0057(11) 0.0008(11) -0.0036(11) C17 0.0677(17) 0.0427(14) 0.0798(18) 0.0022(13) 0.0075(15) -0.0181(13) C18 0.094(2) 0.0570(18) 0.123(3) -0.0107(19) 0.029(2) -0.0092(18) C19 0.103(2) 0.0590(18) 0.103(2) 0.0247(18) 0.009(2) -0.0202(18) C20 0.079(2) 0.089(2) 0.111(3) 0.009(2) -0.010(2) -0.0273(19) C21 0.0599(16) 0.0600(17) 0.0755(18) 0.0046(14) -0.0220(14) -0.0143(14) C22 0.0557(16) 0.0523(15) 0.0684(16) 0.0084(12) -0.0111(13) 0.0001(13) C23 0.0657(17) 0.0507(15) 0.095(2) -0.0097(15) 0.0192(16) -0.0182(14) C24 0.0768(19) 0.0780(19) 0.0517(15) 0.0177(14) 0.0065(14) 0.0081(16) C25 0.086(3) 0.196(5) 0.164(5) -0.040(4) -0.025(3) 0.030(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 C1 1.358(3) . ? O1 H1 0.8200 . ? O2 C15 1.294(3) . ? O2 C14 1.443(4) . ? O3 C15 1.198(3) . ? O4 C9 1.227(3) . ? O5 C16 1.213(3) . ? O6 C16 1.343(3) . ? O6 C17 1.462(3) . ? O7 C7 1.227(3) . ? N1 C7 1.332(3) . ? N1 C8 1.465(3) . ? N1 H1A 0.8600 . ? N2 C9 1.320(3) . ? N2 C10 1.447(3) . ? N2 H2 0.8600 . ? N3 C16 1.339(3) . ? N3 C6 1.460(3) . ? N3 H3 0.8600 . ? C1 C21 1.362(4) . ? C1 C2 1.366(4) . ? C2 C3 1.382(4) . ? C2 H2A 0.9300 . ? C3 C4 1.376(4) . ? C3 H3A 0.9300 . ? C4 C22 1.371(4) . ? C4 C5 1.504(3) . ? C5 C6 1.523(3) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 C7 1.521(3) . ? C6 H6 0.9800 . ? C8 C23 1.521(4) . ? C8 C9 1.528(3) . ? C8 C24 1.536(4) . ? C10 C15 1.499(4) . ? C10 C11 1.538(4) . ? C10 H10 0.9800 . ? C11 C12 1.490(4) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 C13 1.494(5) . ? C12 C25 1.508(6) . ? C12 H12 0.9800 . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? C17 C18 1.501(5) . ? C17 C20 1.504(5) . ? C17 C19 1.516(4) . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? C20 H20A 0.9600 . ? C20 H20B 0.9600 . ? C20 H20C 0.9600 . ? C21 C22 1.380(4) . ? C21 H21 0.9300 . ? C22 H22 0.9300 . ? C23 H23A 0.9600 . ? C23 H23B 0.9600 . ? C23 H23C 0.9600 . ? C24 H24A 0.9600 . ? C24 H24B 0.9600 . ? C24 H24C 0.9600 . ? C25 H25A 0.9600 . ? C25 H25B 0.9600 . ? C25 H25C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 O1 H1 109.5 . . ? C15 O2 C14 117.6(2) . . ? C16 O6 C17 122.3(2) . . ? C7 N1 C8 124.63(18) . . ? C7 N1 H1A 117.7 . . ? C8 N1 H1A 117.7 . . ? C9 N2 C10 122.0(2) . . ? C9 N2 H2 119.0 . . ? C10 N2 H2 119.0 . . ? C16 N3 C6 124.65(19) . . ? C16 N3 H3 117.7 . . ? C6 N3 H3 117.7 . . ? O1 C1 C21 122.1(2) . . ? O1 C1 C2 119.3(2) . . ? C21 C1 C2 118.6(2) . . ? C1 C2 C3 120.7(3) . . ? C1 C2 H2A 119.7 . . ? C3 C2 H2A 119.7 . . ? C4 C3 C2 121.5(3) . . ? C4 C3 H3A 119.2 . . ? C2 C3 H3A 119.2 . . ? C22 C4 C3 116.5(2) . . ? C22 C4 C5 119.1(2) . . ? C3 C4 C5 124.0(2) . . ? C4 C5 C6 118.10(19) . . ? C4 C5 H5A 107.8 . . ? C6 C5 H5A 107.8 . . ? C4 C5 H5B 107.8 . . ? C6 C5 H5B 107.8 . . ? H5A C5 H5B 107.1 . . ? N3 C6 C7 111.44(18) . . ? N3 C6 C5 105.63(17) . . ? C7 C6 C5 110.26(19) . . ? N3 C6 H6 109.8 . . ? C7 C6 H6 109.8 . . ? C5 C6 H6 109.8 . . ? O7 C7 N1 122.5(2) . . ? O7 C7 C6 122.16(19) . . ? N1 C7 C6 115.27(19) . . ? N1 C8 C23 110.5(2) . . ? N1 C8 C9 111.50(18) . . ? C23 C8 C9 111.13(19) . . ? N1 C8 C24 107.10(19) . . ? C23 C8 C24 110.5(2) . . ? C9 C8 C24 105.9(2) . . ? O4 C9 N2 121.6(2) . . ? O4 C9 C8 119.7(2) . . ? N2 C9 C8 118.29(19) . . ? N2 C10 C15 111.8(2) . . ? N2 C10 C11 112.4(2) . . ? C15 C10 C11 111.1(2) . . ? N2 C10 H10 107.1 . . ? C15 C10 H10 107.1 . . ? C11 C10 H10 107.1 . . ? C12 C11 C10 116.1(2) . . ? C12 C11 H11A 108.3 . . ? C10 C11 H11A 108.3 . . ? C12 C11 H11B 108.3 . . ? C10 C11 H11B 108.3 . . ? H11A C11 H11B 107.4 . . ? C11 C12 C13 112.5(3) . . ? C11 C12 C25 111.0(3) . . ? C13 C12 C25 108.8(4) . . ? C11 C12 H12 108.1 . . ? C13 C12 H12 108.1 . . ? C25 C12 H12 108.1 . . ? C12 C13 H13A 109.5 . . ? C12 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C12 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? O2 C14 H14A 109.5 . . ? O2 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? O2 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? O3 C15 O2 123.2(3) . . ? O3 C15 C10 123.4(3) . . ? O2 C15 C10 113.4(2) . . ? O5 C16 N3 125.2(2) . . ? O5 C16 O6 126.1(2) . . ? N3 C16 O6 108.7(2) . . ? O6 C17 C18 110.6(2) . . ? O6 C17 C20 109.4(3) . . ? C18 C17 C20 112.8(3) . . ? O6 C17 C19 101.9(2) . . ? C18 C17 C19 110.0(3) . . ? C20 C17 C19 111.6(3) . . ? C17 C18 H18A 109.5 . . ? C17 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C17 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? 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 . . ? C17 C20 H20A 109.5 . . ? C17 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C17 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C1 C21 C22 120.4(2) . . ? C1 C21 H21 119.8 . . ? C22 C21 H21 119.8 . . ? C4 C22 C21 122.2(2) . . ? C4 C22 H22 118.9 . . ? C21 C22 H22 118.9 . . ? C8 C23 H23A 109.5 . . ? C8 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C8 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C8 C24 H24A 109.5 . . ? C8 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C8 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C12 C25 H25A 109.5 . . ? C12 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? C12 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 22.77 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.223 _refine_diff_density_min -0.151 _refine_diff_density_rms 0.032