# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2003 data_global _journal_coden_Cambridge 177 _publ_contact_author_name 'Stephen A Glover' _publ_contact_author_address ; Division of Chemistry, School of Biological, Biomedical and Molecular Sciences, University of New England, Armidale, NSW 2351, Australia ; _publ_contact_author_email ' sglover@metz.une.edu.au ' _publ_contact_author_phone ' 61 02 67732361 ' _publ_contact_author_fax ' 61 02 37733268 ' _publ_requested_journal 'Journal of Organic and Biolmolecular Chemistry' _publ_section_title ; Crystal structures and properties of mutagenic N-acyloxy-N-alkoxyamides - "most pyramidal" acyclic amides ; loop_ _publ_author_name _publ_author_address 'Ashley-Mae E. Gillson' ; Division of Chemistry, School of Biological, Biomedical and Molecular Sciences, University of New England, Armidale, NSW 2351, Australia ; 'Stephen A. Glover' ; Division of Chemistry, School of Biological, Biomedical and Molecular Sciences, University of New England, Armidale, NSW 2351, Australia ; 'David J. Tucker' ; Division of Chemistry, School of Biological, Biomedical and Molecular Sciences, University of New England, Armidale, NSW 2351, Australia ; 'Peter Turner' ; Crystal Structure Analysis Facility School of Chemistry, University of Sydney, Sydney, NSW 2006, Australia ; data_sag2 _database_code_CSD 212185 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C25 H25 N O4' _chemical_formula_weight 403.46 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/c _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 9.974(3) _cell_length_b 14.182(5) _cell_length_c 16.104(5) _cell_angle_alpha 90.00 _cell_angle_beta 107.088(5) _cell_angle_gamma 90.00 _cell_volume 2177.4(12) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 983 _cell_measurement_theta_min 2.906 _cell_measurement_theta_max 28.228 _exptl_crystal_description prismatic _exptl_crystal_colour colourless _exptl_crystal_size_max 0.445 _exptl_crystal_size_mid 0.310 _exptl_crystal_size_min 0.244 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.231 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 856 _exptl_absorpt_coefficient_mu 0.083 _exptl_absorpt_correction_type Gaussian _exptl_absorpt_correction_T_min 0.963 _exptl_absorpt_correction_T_max 0.979 _exptl_absorpt_process_details ; Gaussian (Coppens et al., 1965) XPREP (Bruker, 1995) ; _exptl_special_details ; ? ; _diffrn_crystal_treatment ; attached with Exxon Paratone N, to a short length of fibre supported on a thin piece of copper wire inserted in a copper mounting pin. The crystal was quenched in a cold nitrogen gas stream from an Oxford Cryosystems Cryostream. ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART 1000 CCD' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number 184 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0.10 _diffrn_reflns_number 18940 _diffrn_reflns_av_R_equivalents 0.0274 _diffrn_reflns_av_sigmaI/netI 0.0171 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.95 _diffrn_reflns_theta_max 28.23 _reflns_number_total 5007 _reflns_number_gt 4069 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker,1995)' _computing_cell_refinement 'SAINT (Bruker,1995)' _computing_data_reduction 'SAINT and XPREP (Bruker 1995)' _computing_structure_solution 'SIR97 (Altomare, et. al. 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ; teXsan for Windows (MSC, 1997), XSHELL (Bruker, 2000) xtal 3.6 (Hall,du Boulay, D.J. & Olthof-Hazekamp, R. 1999) ORTEPII (Johnson,C.K., 1976). WinGX (Farrugia, 1999) ; _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^)+(0.0400P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5007 _refine_ls_number_parameters 274 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0460 _refine_ls_R_factor_gt 0.0349 _refine_ls_wR_factor_ref 0.0951 _refine_ls_wR_factor_gt 0.0908 _refine_ls_goodness_of_fit_ref 1.465 _refine_ls_restrained_S_all 1.465 _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 0.26038(7) 0.46516(5) 0.43436(4) 0.02604(17) Uani 1 1 d . . . O2 O 0.02781(7) 0.49480(5) 0.37669(4) 0.03040(18) Uani 1 1 d . . . O3 O 0.34392(7) 0.45881(5) 0.57991(4) 0.02619(17) Uani 1 1 d . . . O4 O 0.19397(9) 0.29077(5) 0.43682(5) 0.0385(2) Uani 1 1 d . . . N1 N 0.22874(8) 0.43106(6) 0.51069(5) 0.02413(18) Uani 1 1 d . . . C1 C 0.19359(10) 0.55728(6) 0.30869(6) 0.0241(2) Uani 1 1 d . . . C2 C 0.33386(10) 0.57967(7) 0.32145(6) 0.0283(2) Uani 1 1 d . . . H2 H 0.4025 0.5620 0.3738 0.034 Uiso 1 1 calc R . . C3 C 0.37314(12) 0.62799(7) 0.25729(7) 0.0334(2) Uani 1 1 d . . . H3 H 0.4688 0.6437 0.2658 0.040 Uiso 1 1 calc R . . C4 C 0.27292(12) 0.65333(8) 0.18082(7) 0.0352(3) Uani 1 1 d . . . H4 H 0.3004 0.6854 0.1367 0.042 Uiso 1 1 calc R . . C5 C 0.13310(12) 0.63203(8) 0.16856(7) 0.0360(3) Uani 1 1 d . . . H5 H 0.0646 0.6503 0.1164 0.043 Uiso 1 1 calc R . . C6 C 0.09290(11) 0.58418(8) 0.23229(6) 0.0307(2) Uani 1 1 d . . . H6 H -0.0032 0.5697 0.2240 0.037 Uiso 1 1 calc R . . C7 C 0.14613(10) 0.50491(6) 0.37493(6) 0.0233(2) Uani 1 1 d . . . C8 C 0.30183(10) 0.63089(7) 0.55867(6) 0.0266(2) Uani 1 1 d . . . C9 C 0.42055(11) 0.67314(7) 0.54692(7) 0.0295(2) Uani 1 1 d . . . H9 H 0.5104 0.6475 0.5751 0.035 Uiso 1 1 calc R . . C10 C 0.40992(11) 0.75225(7) 0.49472(7) 0.0293(2) Uani 1 1 d . . . H10 H 0.4927 0.7797 0.4877 0.035 Uiso 1 1 calc R . . C11 C 0.27972(10) 0.79237(7) 0.45228(6) 0.0263(2) Uani 1 1 d . . . C12 C 0.16108(10) 0.74850(7) 0.46387(7) 0.0290(2) Uani 1 1 d . . . H12 H 0.0710 0.7734 0.4352 0.035 Uiso 1 1 calc R . . C13 C 0.17140(10) 0.66964(7) 0.51603(6) 0.0292(2) Uani 1 1 d . . . H13 H 0.0887 0.6417 0.5228 0.035 Uiso 1 1 calc R . . C14 C 0.31239(11) 0.54685(7) 0.61713(7) 0.0308(2) Uani 1 1 d . . . H14A H 0.3866 0.5589 0.6723 0.037 Uiso 1 1 calc R . . H14B H 0.2226 0.5396 0.6309 0.037 Uiso 1 1 calc R . . C15 C 0.26341(11) 0.88205(7) 0.39719(7) 0.0310(2) Uani 1 1 d . . . C16 C 0.20712(14) 0.96100(8) 0.44322(8) 0.0460(3) Uani 1 1 d . . . H16A H 0.1138 0.9437 0.4467 0.069 Uiso 1 1 calc R . . H16B H 0.2009 1.0198 0.4104 0.069 Uiso 1 1 calc R . . H16C H 0.2708 0.9698 0.5020 0.069 Uiso 1 1 calc R . . C17 C 0.40252(13) 0.91436(9) 0.38455(9) 0.0508(3) Uani 1 1 d . . . H17A H 0.4692 0.9289 0.4412 0.076 Uiso 1 1 calc R . . H17B H 0.3867 0.9709 0.3479 0.076 Uiso 1 1 calc R . . H17C H 0.4407 0.8640 0.3564 0.076 Uiso 1 1 calc R . . C18 C 0.16014(13) 0.86452(8) 0.30704(7) 0.0417(3) Uani 1 1 d . . . H18A H 0.1949 0.8130 0.2785 0.063 Uiso 1 1 calc R . . H18B H 0.1512 0.9219 0.2719 0.063 Uiso 1 1 calc R . . H18C H 0.0683 0.8475 0.3131 0.063 Uiso 1 1 calc R . . C19 C 0.22487(10) 0.28071(7) 0.58907(6) 0.0253(2) Uani 1 1 d . . . C20 C 0.25165(11) 0.18431(7) 0.59175(7) 0.0325(2) Uani 1 1 d . . . H20 H 0.2630 0.1533 0.5420 0.039 Uiso 1 1 calc R . . C21 C 0.26181(12) 0.13329(8) 0.66674(8) 0.0395(3) Uani 1 1 d . . . H21 H 0.2811 0.0676 0.6685 0.047 Uiso 1 1 calc R . . C22 C 0.24387(12) 0.17787(8) 0.73880(7) 0.0368(3) Uani 1 1 d . . . H22 H 0.2531 0.1431 0.7906 0.044 Uiso 1 1 calc R . . C23 C 0.21250(11) 0.27300(8) 0.73582(7) 0.0343(3) Uani 1 1 d . . . H23 H 0.1976 0.3030 0.7851 0.041 Uiso 1 1 calc R . . C24 C 0.20265(11) 0.32471(7) 0.66135(7) 0.0300(2) Uani 1 1 d . . . H24 H 0.1808 0.3900 0.6595 0.036 Uiso 1 1 calc R . . C25 C 0.21768(10) 0.32973(7) 0.50628(6) 0.0264(2) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0285(4) 0.0295(4) 0.0225(3) 0.0066(3) 0.0111(3) 0.0051(3) O2 0.0272(4) 0.0361(4) 0.0280(4) 0.0025(3) 0.0082(3) -0.0010(3) O3 0.0266(4) 0.0259(4) 0.0241(4) 0.0006(3) 0.0044(3) 0.0003(3) O4 0.0573(5) 0.0320(4) 0.0272(4) -0.0041(3) 0.0142(4) -0.0028(3) N1 0.0278(4) 0.0264(4) 0.0187(4) 0.0038(3) 0.0077(3) 0.0003(3) C1 0.0309(5) 0.0201(5) 0.0219(5) -0.0010(4) 0.0089(4) 0.0012(4) C2 0.0301(5) 0.0287(5) 0.0258(5) 0.0010(4) 0.0080(4) 0.0010(4) C3 0.0351(6) 0.0331(6) 0.0351(6) 0.0028(5) 0.0150(5) -0.0023(4) C4 0.0488(7) 0.0310(6) 0.0298(6) 0.0051(4) 0.0176(5) -0.0012(5) C5 0.0438(7) 0.0369(6) 0.0244(5) 0.0064(4) 0.0055(5) 0.0010(5) C6 0.0316(6) 0.0315(6) 0.0268(5) 0.0014(4) 0.0052(4) -0.0007(4) C7 0.0267(5) 0.0217(5) 0.0209(5) -0.0022(4) 0.0062(4) 0.0010(4) C8 0.0326(5) 0.0239(5) 0.0247(5) -0.0050(4) 0.0105(4) -0.0008(4) C9 0.0271(5) 0.0293(5) 0.0319(6) 0.0005(4) 0.0083(4) 0.0040(4) C10 0.0264(5) 0.0289(5) 0.0341(6) -0.0001(4) 0.0110(4) -0.0017(4) C11 0.0296(5) 0.0240(5) 0.0251(5) -0.0044(4) 0.0077(4) -0.0002(4) C12 0.0247(5) 0.0293(5) 0.0312(5) -0.0045(4) 0.0053(4) 0.0017(4) C13 0.0279(5) 0.0278(5) 0.0334(6) -0.0059(4) 0.0116(4) -0.0045(4) C14 0.0399(6) 0.0278(6) 0.0266(5) -0.0028(4) 0.0127(5) -0.0019(4) C15 0.0340(6) 0.0278(5) 0.0302(5) 0.0014(4) 0.0078(4) 0.0017(4) C16 0.0694(9) 0.0275(6) 0.0394(7) -0.0003(5) 0.0132(6) 0.0085(5) C17 0.0443(7) 0.0465(7) 0.0607(8) 0.0225(6) 0.0141(6) -0.0034(6) C18 0.0506(7) 0.0403(7) 0.0306(6) 0.0020(5) 0.0061(5) 0.0056(5) C19 0.0235(5) 0.0256(5) 0.0275(5) 0.0026(4) 0.0085(4) -0.0004(4) C20 0.0377(6) 0.0271(6) 0.0360(6) 0.0010(4) 0.0161(5) 0.0003(4) C21 0.0488(7) 0.0248(6) 0.0492(7) 0.0104(5) 0.0212(6) 0.0047(5) C22 0.0417(6) 0.0348(6) 0.0356(6) 0.0122(5) 0.0141(5) -0.0004(5) C23 0.0412(6) 0.0347(6) 0.0304(6) 0.0028(5) 0.0161(5) -0.0015(5) C24 0.0351(6) 0.0254(5) 0.0324(6) 0.0029(4) 0.0143(4) 0.0012(4) C25 0.0268(5) 0.0266(5) 0.0268(5) 0.0002(4) 0.0093(4) 0.0021(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C7 1.3752(12) . ? O1 N1 1.4396(10) . ? O2 C7 1.1974(12) . ? O3 N1 1.4017(10) . ? O3 C14 1.4586(13) . ? O4 C25 1.2070(12) . ? N1 C25 1.4414(14) . ? C1 C2 1.3898(15) . ? C1 C6 1.3934(14) . ? C1 C7 1.4868(13) . ? C2 C3 1.3887(14) . ? C2 H2 0.9500 . ? C3 C4 1.3861(15) . ? C3 H3 0.9500 . ? C4 C5 1.3833(16) . ? C4 H4 0.9500 . ? C5 C6 1.3844(14) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? C8 C9 1.3888(14) . ? C8 C13 1.3931(14) . ? C8 C14 1.5032(14) . ? C9 C10 1.3871(15) . ? C9 H9 0.9500 . ? C10 C11 1.3984(14) . ? C10 H10 0.9500 . ? C11 C12 1.3971(15) . ? C11 C15 1.5318(14) . ? C12 C13 1.3843(15) . ? C12 H12 0.9500 . ? C13 H13 0.9500 . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C15 C17 1.5307(16) . ? C15 C18 1.5335(16) . ? C15 C16 1.5372(15) . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C19 C20 1.3912(14) . ? C19 C24 1.3947(14) . ? C19 C25 1.4866(14) . ? C20 C21 1.3857(15) . ? C20 H20 0.9500 . ? C21 C22 1.3785(16) . ? C21 H21 0.9500 . ? C22 C23 1.3826(16) . ? C22 H22 0.9500 . ? C23 C24 1.3844(14) . ? C23 H23 0.9500 . ? C24 H24 0.9500 . ? 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 C7 O1 N1 112.78(7) . . ? N1 O3 C14 109.98(7) . . ? O3 N1 O1 104.52(7) . . ? O3 N1 C25 110.62(7) . . ? O1 N1 C25 109.00(7) . . ? C2 C1 C6 120.07(9) . . ? C2 C1 C7 121.80(9) . . ? C6 C1 C7 118.13(9) . . ? C3 C2 C1 119.64(9) . . ? C3 C2 H2 120.2 . . ? C1 C2 H2 120.2 . . ? C4 C3 C2 120.10(10) . . ? C4 C3 H3 120.0 . . ? C2 C3 H3 120.0 . . ? C5 C4 C3 120.26(10) . . ? C5 C4 H4 119.9 . . ? C3 C4 H4 119.9 . . ? C4 C5 C6 120.04(10) . . ? C4 C5 H5 120.0 . . ? C6 C5 H5 120.0 . . ? C5 C6 C1 119.88(10) . . ? C5 C6 H6 120.1 . . ? C1 C6 H6 120.1 . . ? O2 C7 O1 123.74(9) . . ? O2 C7 C1 126.91(9) . . ? O1 C7 C1 109.31(8) . . ? C9 C8 C13 118.22(9) . . ? C9 C8 C14 121.45(9) . . ? C13 C8 C14 120.32(9) . . ? C10 C9 C8 121.01(9) . . ? C10 C9 H9 119.5 . . ? C8 C9 H9 119.5 . . ? C9 C10 C11 121.32(9) . . ? C9 C10 H10 119.3 . . ? C11 C10 H10 119.3 . . ? C12 C11 C10 117.06(10) . . ? C12 C11 C15 119.81(9) . . ? C10 C11 C15 123.10(9) . . ? C13 C12 C11 121.73(9) . . ? C13 C12 H12 119.1 . . ? C11 C12 H12 119.1 . . ? C12 C13 C8 120.66(9) . . ? C12 C13 H13 119.7 . . ? C8 C13 H13 119.7 . . ? O3 C14 C8 113.91(8) . . ? O3 C14 H14A 108.8 . . ? C8 C14 H14A 108.8 . . ? O3 C14 H14B 108.8 . . ? C8 C14 H14B 108.8 . . ? H14A C14 H14B 107.7 . . ? C17 C15 C11 112.30(9) . . ? C17 C15 C18 107.79(10) . . ? C11 C15 C18 109.95(9) . . ? C17 C15 C16 108.66(10) . . ? C11 C15 C16 108.49(9) . . ? C18 C15 C16 109.61(9) . . ? C15 C16 H16A 109.5 . . ? C15 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C15 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C15 C17 H17A 109.5 . . ? C15 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C15 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C15 C18 H18A 109.5 . . ? C15 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C15 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C20 C19 C24 119.33(9) . . ? C20 C19 C25 116.47(9) . . ? C24 C19 C25 124.17(9) . . ? C21 C20 C19 120.29(10) . . ? C21 C20 H20 119.9 . . ? C19 C20 H20 119.9 . . ? C22 C21 C20 119.99(10) . . ? C22 C21 H21 120.0 . . ? C20 C21 H21 120.0 . . ? C21 C22 C23 120.15(10) . . ? C21 C22 H22 119.9 . . ? C23 C22 H22 119.9 . . ? C22 C23 C24 120.32(10) . . ? C22 C23 H23 119.8 . . ? C24 C23 H23 119.8 . . ? C23 C24 C19 119.85(10) . . ? C23 C24 H24 120.1 . . ? C19 C24 H24 120.1 . . ? O4 C25 N1 119.57(9) . . ? O4 C25 C19 124.17(10) . . ? N1 C25 C19 116.05(8) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C14 O3 N1 O1 96.66(8) . . . . ? C14 O3 N1 C25 -146.17(8) . . . . ? C7 O1 N1 O3 -137.61(7) . . . . ? C7 O1 N1 C25 104.11(8) . . . . ? C6 C1 C2 C3 -0.72(14) . . . . ? C7 C1 C2 C3 179.45(9) . . . . ? C1 C2 C3 C4 -0.28(15) . . . . ? C2 C3 C4 C5 1.05(16) . . . . ? C3 C4 C5 C6 -0.82(17) . . . . ? C4 C5 C6 C1 -0.18(16) . . . . ? C2 C1 C6 C5 0.95(15) . . . . ? C7 C1 C6 C5 -179.21(9) . . . . ? N1 O1 C7 O2 -15.09(12) . . . . ? N1 O1 C7 C1 167.15(7) . . . . ? C2 C1 C7 O2 167.62(10) . . . . ? C6 C1 C7 O2 -12.22(15) . . . . ? C2 C1 C7 O1 -14.71(12) . . . . ? C6 C1 C7 O1 165.46(8) . . . . ? C13 C8 C9 C10 0.50(15) . . . . ? C14 C8 C9 C10 -178.20(9) . . . . ? C8 C9 C10 C11 0.13(16) . . . . ? C9 C10 C11 C12 -0.85(15) . . . . ? C9 C10 C11 C15 177.32(9) . . . . ? C10 C11 C12 C13 0.96(15) . . . . ? C15 C11 C12 C13 -177.27(9) . . . . ? C11 C12 C13 C8 -0.35(15) . . . . ? C9 C8 C13 C12 -0.39(15) . . . . ? C14 C8 C13 C12 178.32(9) . . . . ? N1 O3 C14 C8 -69.27(10) . . . . ? C9 C8 C14 O3 -75.63(12) . . . . ? C13 C8 C14 O3 105.69(11) . . . . ? C12 C11 C15 C17 -174.40(10) . . . . ? C10 C11 C15 C17 7.48(14) . . . . ? C12 C11 C15 C18 -54.38(12) . . . . ? C10 C11 C15 C18 127.50(11) . . . . ? C12 C11 C15 C16 65.49(12) . . . . ? C10 C11 C15 C16 -112.63(11) . . . . ? C24 C19 C20 C21 -2.61(15) . . . . ? C25 C19 C20 C21 179.21(10) . . . . ? C19 C20 C21 C22 0.69(17) . . . . ? C20 C21 C22 C23 1.51(17) . . . . ? C21 C22 C23 C24 -1.76(17) . . . . ? C22 C23 C24 C19 -0.18(16) . . . . ? C20 C19 C24 C23 2.35(15) . . . . ? C25 C19 C24 C23 -179.61(9) . . . . ? O3 N1 C25 O4 -135.77(9) . . . . ? O1 N1 C25 O4 -21.39(12) . . . . ? O3 N1 C25 C19 49.25(10) . . . . ? O1 N1 C25 C19 163.63(7) . . . . ? C20 C19 C25 O4 21.76(14) . . . . ? C24 C19 C25 O4 -156.32(11) . . . . ? C20 C19 C25 N1 -163.52(9) . . . . ? C24 C19 C25 N1 18.39(14) . . . . ? _diffrn_measured_fraction_theta_max 0.930 _diffrn_reflns_theta_full 28.23 _diffrn_measured_fraction_theta_full 0.930 _refine_diff_density_max 0.222 _refine_diff_density_min -0.203 _refine_diff_density_rms 0.039 #===END data_sag3 _database_code_CSD 212186 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C33 H41 N O4' _chemical_formula_weight 515.67 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n ' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 9.2910(19) _cell_length_b 17.063(4) _cell_length_c 18.640(4) _cell_angle_alpha 90.00 _cell_angle_beta 98.007(4) _cell_angle_gamma 90.00 _cell_volume 2926.2(11) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 932 _cell_measurement_theta_min 28.029 _cell_measurement_theta_max 2.332 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.465 _exptl_crystal_size_mid 0.174 _exptl_crystal_size_min 0.173 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.171 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1112 _exptl_absorpt_coefficient_mu 0.076 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _diffrn_crystal_treatment ; attached with Exxon Paratone N, to a short length of fibre supported on a thin piece of copper wire inserted in a copper mounting pin. The crystal was quenched in a cold nitrogen gas stream from an Oxford Cryosystems Cryostream. ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART 1000 CCD' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number 233 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0.03 _diffrn_reflns_number 29776 _diffrn_reflns_av_R_equivalents 0.0300 _diffrn_reflns_av_sigmaI/netI 0.0242 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 1.63 _diffrn_reflns_theta_max 28.28 _reflns_number_total 7092 _reflns_number_gt 5242 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker,1995)' _computing_cell_refinement 'SAINT (Bruker,1995)' _computing_data_reduction 'SAINT and XPREP (Bruker 1995)' _computing_structure_solution 'SIR97 (Altomare, et. al. 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ; teXsan for Windows (MSC, 1997) xtal 3.6 (Hall,du Boulay, D.J. & Olthof-Hazekamp, R. 1999) ORTEPII (Johnson,C.K., 1976). WinGX (Farrugia, 1999) ; _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^)+(0.02P)^2^+0.5P] 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_number_reflns 7092 _refine_ls_number_parameters 352 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0607 _refine_ls_R_factor_gt 0.0425 _refine_ls_wR_factor_ref 0.0909 _refine_ls_wR_factor_gt 0.0863 _refine_ls_goodness_of_fit_ref 1.318 _refine_ls_restrained_S_all 1.318 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.43830(10) 0.42571(5) 0.15084(4) 0.0309(2) Uani 1 1 d . . . O2 O 0.59934(11) 0.51008(6) 0.11150(5) 0.0387(2) Uani 1 1 d . . . O3 O 0.28450(9) 0.36392(5) 0.06418(5) 0.0306(2) Uani 1 1 d . . . O4 O 0.62065(11) 0.31569(6) 0.13662(5) 0.0411(2) Uani 1 1 d . . . N1 N 0.42903(11) 0.38885(6) 0.08076(6) 0.0294(2) Uani 1 1 d . . . C1 C 0.51465(13) 0.53254(7) 0.22523(7) 0.0258(3) Uani 1 1 d . . . C2 C 0.42769(15) 0.50655(8) 0.27505(7) 0.0355(3) Uani 1 1 d . . . H2 H 0.3711 0.4604 0.2656 0.043 Uiso 1 1 calc R . . C3 C 0.42335(15) 0.54801(8) 0.33853(8) 0.0390(3) Uani 1 1 d . . . H3 H 0.3644 0.5290 0.3725 0.047 Uiso 1 1 calc R . . C4 C 0.50266(13) 0.61685(7) 0.35432(7) 0.0293(3) Uani 1 1 d . . . C5 C 0.58981(14) 0.64201(7) 0.30386(7) 0.0297(3) Uani 1 1 d . . . H5 H 0.6458 0.6885 0.3130 0.036 Uiso 1 1 calc R . . C6 C 0.59628(14) 0.60038(7) 0.24045(7) 0.0288(3) Uani 1 1 d . . . H6 H 0.6572 0.6184 0.2070 0.035 Uiso 1 1 calc R . . C7 C 0.52545(13) 0.49097(7) 0.15624(7) 0.0272(3) Uani 1 1 d . . . C8 C 0.49660(14) 0.65960(8) 0.42626(7) 0.0348(3) Uani 1 1 d . . . C9 C 0.5513(2) 0.74387(9) 0.42445(9) 0.0561(5) Uani 1 1 d . . . H9A H 0.4930 0.7724 0.3850 0.084 Uiso 1 1 calc R . . H9B H 0.6534 0.7437 0.4165 0.084 Uiso 1 1 calc R . . H9C H 0.5427 0.7696 0.4707 0.084 Uiso 1 1 calc R . . C10 C 0.59289(19) 0.61420(11) 0.48579(9) 0.0578(5) Uani 1 1 d . . . H10A H 0.5892 0.6395 0.5327 0.087 Uiso 1 1 calc R . . H10B H 0.6933 0.6139 0.4753 0.087 Uiso 1 1 calc R . . H10C H 0.5577 0.5602 0.4874 0.087 Uiso 1 1 calc R . . C11A C 0.34111(16) 0.66162(11) 0.44445(9) 0.0543(5) Uani 1 1 d . . . H11A H 0.2774 0.6870 0.4049 0.081 Uiso 1 1 calc R . . H11B H 0.3389 0.6912 0.4893 0.081 Uiso 1 1 calc R . . H11C H 0.3074 0.6080 0.4508 0.081 Uiso 1 1 calc R . . C12 C 0.16699(14) 0.49341(8) 0.06088(7) 0.0289(3) Uani 1 1 d . . . C13 C 0.06798(15) 0.48975(8) 0.11015(7) 0.0343(3) Uani 1 1 d . . . H13 H 0.0174 0.4422 0.1157 0.041 Uiso 1 1 calc R . . C14 C 0.04215(15) 0.55426(8) 0.15124(7) 0.0336(3) Uani 1 1 d . . . H14 H -0.0265 0.5502 0.1844 0.040 Uiso 1 1 calc R . . C15 C 0.11420(13) 0.62531(7) 0.14540(6) 0.0276(3) Uani 1 1 d . . . C16 C 0.21056(14) 0.62874(8) 0.09461(7) 0.0325(3) Uani 1 1 d . . . H16 H 0.2599 0.6765 0.0883 0.039 Uiso 1 1 calc R . . C17 C 0.23635(14) 0.56405(8) 0.05293(7) 0.0333(3) Uani 1 1 d . . . H17 H 0.3024 0.5684 0.0185 0.040 Uiso 1 1 calc R . . C18 C 0.19966(15) 0.42203(8) 0.01861(7) 0.0335(3) Uani 1 1 d . . . H18A H 0.1072 0.3980 -0.0037 0.040 Uiso 1 1 calc R . . H18B H 0.2543 0.4380 -0.0209 0.040 Uiso 1 1 calc R . . C19 C 0.08470(15) 0.69656(8) 0.19125(7) 0.0326(3) Uani 1 1 d . . . C20 C 0.2156(2) 0.75057(11) 0.20399(13) 0.0798(7) Uani 1 1 d . . . H20A H 0.2342 0.7728 0.1577 0.120 Uiso 1 1 calc R . . H20B H 0.3008 0.7208 0.2257 0.120 Uiso 1 1 calc R . . H20C H 0.1962 0.7930 0.2367 0.120 Uiso 1 1 calc R . . C21 C 0.0474(3) 0.67119(11) 0.26481(9) 0.0813(7) Uani 1 1 d . . . H21A H 0.0328 0.7177 0.2938 0.122 Uiso 1 1 calc R . . H21B H 0.1273 0.6397 0.2899 0.122 Uiso 1 1 calc R . . H21C H -0.0418 0.6398 0.2580 0.122 Uiso 1 1 calc R . . C22 C -0.0443(2) 0.74098(11) 0.15255(10) 0.0717(6) Uani 1 1 d . . . H22A H -0.0677 0.7849 0.1828 0.108 Uiso 1 1 calc R . . H22B H -0.1282 0.7058 0.1435 0.108 Uiso 1 1 calc R . . H22C H -0.0205 0.7610 0.1064 0.108 Uiso 1 1 calc R . . C23 C 0.49829(13) 0.26654(7) 0.02469(7) 0.0262(3) Uani 1 1 d . . . C24 C 0.52482(13) 0.18738(7) 0.03885(7) 0.0296(3) Uani 1 1 d . . . H24 H 0.5583 0.1705 0.0868 0.036 Uiso 1 1 calc R . . C25 C 0.50267(13) 0.13335(7) -0.01663(7) 0.0290(3) Uani 1 1 d . . . H25 H 0.5182 0.0794 -0.0058 0.035 Uiso 1 1 calc R . . C26 C 0.45796(12) 0.15580(7) -0.08831(7) 0.0257(3) Uani 1 1 d . . . C27 C 0.43568(14) 0.23551(7) -0.10174(7) 0.0285(3) Uani 1 1 d . . . H27 H 0.4078 0.2528 -0.1501 0.034 Uiso 1 1 calc R . . C28 C 0.45316(13) 0.29034(7) -0.04610(7) 0.0282(3) Uani 1 1 d . . . H28 H 0.4342 0.3442 -0.0565 0.034 Uiso 1 1 calc R . . C29 C 0.52385(14) 0.32176(7) 0.08669(7) 0.0295(3) Uani 1 1 d . . . C30 C 0.43538(14) 0.09334(8) -0.14781(7) 0.0331(3) Uani 1 1 d . . . C31 C 0.39322(18) 0.12852(9) -0.22340(8) 0.0460(4) Uani 1 1 d . . . H31A H 0.3021 0.1578 -0.2248 0.069 Uiso 1 1 calc R . . H31B H 0.3804 0.0863 -0.2594 0.069 Uiso 1 1 calc R . . H31C H 0.4702 0.1640 -0.2344 0.069 Uiso 1 1 calc R . . C32 C 0.31379(18) 0.03776(9) -0.13161(9) 0.0529(4) Uani 1 1 d . . . H32A H 0.3402 0.0144 -0.0835 0.079 Uiso 1 1 calc R . . H32B H 0.3006 -0.0038 -0.1682 0.079 Uiso 1 1 calc R . . H32C H 0.2230 0.0672 -0.1327 0.079 Uiso 1 1 calc R . . C33 C 0.57756(17) 0.04690(9) -0.14718(8) 0.0472(4) Uani 1 1 d . . . H33A H 0.6561 0.0828 -0.1551 0.071 Uiso 1 1 calc R . . H33B H 0.5650 0.0075 -0.1858 0.071 Uiso 1 1 calc R . . H33C H 0.6021 0.0208 -0.1002 0.071 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 0.0387(5) 0.0289(5) 0.0264(5) -0.0079(4) 0.0100(4) -0.0061(4) O2 0.0453(6) 0.0407(6) 0.0328(5) -0.0050(4) 0.0148(4) -0.0107(5) O3 0.0279(5) 0.0289(5) 0.0354(5) -0.0047(4) 0.0056(4) -0.0017(4) O4 0.0393(6) 0.0455(6) 0.0360(5) -0.0094(5) -0.0037(4) 0.0041(5) N1 0.0304(6) 0.0309(6) 0.0276(5) -0.0091(5) 0.0061(4) -0.0033(5) C1 0.0252(6) 0.0244(6) 0.0274(6) -0.0010(5) 0.0025(5) 0.0026(5) C2 0.0338(7) 0.0346(7) 0.0398(8) -0.0118(6) 0.0119(6) -0.0120(6) C3 0.0353(7) 0.0448(8) 0.0404(8) -0.0128(7) 0.0175(6) -0.0129(6) C4 0.0223(6) 0.0314(7) 0.0336(7) -0.0075(6) 0.0021(5) 0.0027(5) C5 0.0312(7) 0.0221(6) 0.0348(7) -0.0011(5) 0.0008(5) -0.0013(5) C6 0.0307(7) 0.0260(6) 0.0301(7) 0.0035(5) 0.0054(5) -0.0003(5) C7 0.0272(6) 0.0250(6) 0.0292(6) -0.0001(5) 0.0029(5) 0.0004(5) C8 0.0269(7) 0.0406(8) 0.0366(7) -0.0147(6) 0.0032(6) -0.0006(6) C9 0.0655(11) 0.0447(9) 0.0608(11) -0.0273(8) 0.0190(9) -0.0099(8) C10 0.0596(11) 0.0674(12) 0.0426(9) -0.0169(8) -0.0058(8) 0.0116(9) C11A 0.0349(8) 0.0790(12) 0.0510(9) -0.0354(9) 0.0132(7) -0.0048(8) C12 0.0283(6) 0.0319(7) 0.0263(6) -0.0004(5) 0.0029(5) 0.0029(5) C13 0.0381(7) 0.0295(7) 0.0369(7) 0.0012(6) 0.0111(6) -0.0032(6) C14 0.0355(7) 0.0356(7) 0.0325(7) 0.0017(6) 0.0144(6) 0.0009(6) C15 0.0270(6) 0.0293(7) 0.0252(6) 0.0025(5) -0.0005(5) 0.0057(5) C16 0.0324(7) 0.0298(7) 0.0357(7) 0.0027(6) 0.0065(6) -0.0038(6) C17 0.0315(7) 0.0385(8) 0.0318(7) 0.0006(6) 0.0112(6) -0.0009(6) C18 0.0340(7) 0.0372(7) 0.0290(7) -0.0037(6) 0.0031(5) 0.0023(6) C19 0.0376(7) 0.0286(7) 0.0318(7) 0.0008(5) 0.0051(6) 0.0072(6) C20 0.0597(12) 0.0611(12) 0.1221(18) -0.0531(13) 0.0254(12) -0.0127(10) C21 0.165(2) 0.0449(10) 0.0403(10) -0.0078(8) 0.0379(12) 0.0036(12) C22 0.0781(13) 0.0662(12) 0.0667(12) -0.0101(10) -0.0044(10) 0.0429(11) C23 0.0222(6) 0.0288(6) 0.0287(6) -0.0035(5) 0.0070(5) -0.0007(5) C24 0.0287(7) 0.0333(7) 0.0267(6) 0.0015(5) 0.0031(5) 0.0038(5) C25 0.0298(6) 0.0229(6) 0.0342(7) 0.0013(5) 0.0044(5) 0.0032(5) C26 0.0206(6) 0.0260(6) 0.0306(6) -0.0032(5) 0.0044(5) 0.0005(5) C27 0.0315(7) 0.0285(7) 0.0257(6) 0.0009(5) 0.0046(5) 0.0031(5) C28 0.0315(7) 0.0224(6) 0.0320(7) 0.0000(5) 0.0086(5) 0.0017(5) C29 0.0287(7) 0.0307(7) 0.0300(7) -0.0021(6) 0.0077(5) -0.0027(5) C30 0.0349(7) 0.0277(7) 0.0346(7) -0.0073(6) -0.0025(6) 0.0028(6) C31 0.0601(10) 0.0423(9) 0.0328(8) -0.0118(7) -0.0036(7) 0.0107(7) C32 0.0523(10) 0.0415(9) 0.0601(10) -0.0074(8) -0.0096(8) -0.0152(7) C33 0.0510(9) 0.0407(8) 0.0476(9) -0.0179(7) -0.0015(7) 0.0147(7) _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 C7 1.3723(15) . ? O1 N1 1.4414(13) . ? O2 C7 1.1968(15) . ? O3 N1 1.4014(13) . ? O3 C18 1.4626(15) . ? O4 C29 1.2052(15) . ? N1 C29 1.4394(16) . ? C1 C2 1.3861(17) . ? C1 C6 1.3913(17) . ? C1 C7 1.4841(17) . ? C2 C3 1.3839(18) . ? C2 H2 0.9500 . ? C3 C4 1.3960(18) . ? C3 H3 0.9500 . ? C4 C5 1.3919(18) . ? C4 C8 1.5344(18) . ? C5 C6 1.3874(18) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? C8 C9 1.527(2) . ? C8 C11A 1.5296(19) . ? C8 C10 1.535(2) . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11A H11A 0.9800 . ? C11A H11B 0.9800 . ? C11A H11C 0.9800 . ? C12 C17 1.3845(18) . ? C12 C13 1.3889(17) . ? C12 C18 1.5043(18) . ? C13 C14 1.3810(18) . ? C13 H13 0.9500 . ? C14 C15 1.3965(18) . ? C14 H14 0.9500 . ? C15 C16 1.3918(18) . ? C15 C19 1.5327(18) . ? C16 C17 1.3897(18) . ? C16 H16 0.9500 . ? C17 H17 0.9500 . ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? C19 C22 1.513(2) . ? C19 C20 1.518(2) . ? C19 C21 1.523(2) . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? C23 C28 1.3885(17) . ? C23 C24 1.3918(17) . ? C23 C29 1.4843(17) . ? C24 C25 1.3792(18) . ? C24 H24 0.9500 . ? C25 C26 1.3964(17) . ? C25 H25 0.9500 . ? C26 C27 1.3931(17) . ? C26 C30 1.5314(17) . ? C27 C28 1.3893(17) . ? C27 H27 0.9500 . ? C28 H28 0.9500 . ? C30 C31 1.5313(19) . ? C30 C32 1.537(2) . ? C30 C33 1.5392(19) . ? C31 H31A 0.9800 . ? C31 H31B 0.9800 . ? C31 H31C 0.9800 . ? C32 H32A 0.9800 . ? C32 H32B 0.9800 . ? C32 H32C 0.9800 . ? C33 H33A 0.9800 . ? C33 H33B 0.9800 . ? C33 H33C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C7 O1 N1 112.37(9) . . ? N1 O3 C18 110.16(9) . . ? O3 N1 C29 109.44(9) . . ? O3 N1 O1 105.48(8) . . ? C29 N1 O1 108.59(9) . . ? C2 C1 C6 118.79(11) . . ? C2 C1 C7 122.94(11) . . ? C6 C1 C7 118.27(11) . . ? C3 C2 C1 119.90(12) . . ? C3 C2 H2 120.0 . . ? C1 C2 H2 120.0 . . ? C2 C3 C4 122.21(12) . . ? C2 C3 H3 118.9 . . ? C4 C3 H3 118.9 . . ? C5 C4 C3 117.18(12) . . ? C5 C4 C8 122.66(11) . . ? C3 C4 C8 120.12(12) . . ? C6 C5 C4 121.07(12) . . ? C6 C5 H5 119.5 . . ? C4 C5 H5 119.5 . . ? C5 C6 C1 120.84(12) . . ? C5 C6 H6 119.6 . . ? C1 C6 H6 119.6 . . ? O2 C7 O1 124.05(11) . . ? O2 C7 C1 126.01(12) . . ? O1 C7 C1 109.93(10) . . ? C9 C8 C11A 108.14(13) . . ? C9 C8 C4 112.05(12) . . ? C11A C8 C4 110.80(11) . . ? C9 C8 C10 109.21(13) . . ? C11A C8 C10 108.94(13) . . ? C4 C8 C10 107.65(11) . . ? C8 C9 H9A 109.5 . . ? C8 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C8 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C8 C10 H10A 109.5 . . ? C8 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C8 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C8 C11A H11A 109.5 . . ? C8 C11A H11B 109.5 . . ? H11A C11A H11B 109.5 . . ? C8 C11A H11C 109.5 . . ? H11A C11A H11C 109.5 . . ? H11B C11A H11C 109.5 . . ? C17 C12 C13 118.10(12) . . ? C17 C12 C18 121.20(11) . . ? C13 C12 C18 120.69(12) . . ? C14 C13 C12 120.87(12) . . ? C14 C13 H13 119.6 . . ? C12 C13 H13 119.6 . . ? C13 C14 C15 121.77(12) . . ? C13 C14 H14 119.1 . . ? C15 C14 H14 119.1 . . ? C16 C15 C14 116.76(12) . . ? C16 C15 C19 121.87(12) . . ? C14 C15 C19 121.34(11) . . ? C17 C16 C15 121.62(12) . . ? C17 C16 H16 119.2 . . ? C15 C16 H16 119.2 . . ? C12 C17 C16 120.83(12) . . ? C12 C17 H17 119.6 . . ? C16 C17 H17 119.6 . . ? O3 C18 C12 112.12(10) . . ? O3 C18 H18A 109.2 . . ? C12 C18 H18A 109.2 . . ? O3 C18 H18B 109.2 . . ? C12 C18 H18B 109.2 . . ? H18A C18 H18B 107.9 . . ? C22 C19 C20 109.53(15) . . ? C22 C19 C21 107.89(15) . . ? C20 C19 C21 108.03(15) . . ? C22 C19 C15 108.83(12) . . ? C20 C19 C15 111.54(12) . . ? C21 C19 C15 110.94(12) . . ? C19 C20 H20A 109.5 . . ? C19 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C19 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C19 C21 H21A 109.5 . . ? C19 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C19 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C19 C22 H22A 109.5 . . ? C19 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C19 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C28 C23 C24 119.08(11) . . ? C28 C23 C29 123.27(11) . . ? C24 C23 C29 117.62(11) . . ? C25 C24 C23 120.17(12) . . ? C25 C24 H24 119.9 . . ? C23 C24 H24 119.9 . . ? C24 C25 C26 121.84(12) . . ? C24 C25 H25 119.1 . . ? C26 C25 H25 119.1 . . ? C27 C26 C25 117.17(11) . . ? C27 C26 C30 123.19(11) . . ? C25 C26 C30 119.64(11) . . ? C28 C27 C26 121.62(12) . . ? C28 C27 H27 119.2 . . ? C26 C27 H27 119.2 . . ? C23 C28 C27 120.06(12) . . ? C23 C28 H28 120.0 . . ? C27 C28 H28 120.0 . . ? O4 C29 N1 120.70(11) . . ? O4 C29 C23 124.60(12) . . ? N1 C29 C23 114.54(11) . . ? C31 C30 C26 112.66(11) . . ? C31 C30 C32 108.78(12) . . ? C26 C30 C32 108.51(11) . . ? C31 C30 C33 108.54(12) . . ? C26 C30 C33 108.78(11) . . ? C32 C30 C33 109.54(12) . . ? C30 C31 H31A 109.5 . . ? C30 C31 H31B 109.5 . . ? H31A C31 H31B 109.5 . . ? C30 C31 H31C 109.5 . . ? H31A C31 H31C 109.5 . . ? H31B C31 H31C 109.5 . . ? C30 C32 H32A 109.5 . . ? C30 C32 H32B 109.5 . . ? H32A C32 H32B 109.5 . . ? C30 C32 H32C 109.5 . . ? H32A C32 H32C 109.5 . . ? H32B C32 H32C 109.5 . . ? C30 C33 H33A 109.5 . . ? C30 C33 H33B 109.5 . . ? H33A C33 H33B 109.5 . . ? C30 C33 H33C 109.5 . . ? H33A C33 H33C 109.5 . . ? H33B C33 H33C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C18 O3 N1 C29 -147.14(10) . . . . ? C18 O3 N1 O1 96.21(10) . . . . ? C7 O1 N1 O3 -141.60(9) . . . . ? C7 O1 N1 C29 101.17(11) . . . . ? C6 C1 C2 C3 0.0(2) . . . . ? C7 C1 C2 C3 179.66(13) . . . . ? C1 C2 C3 C4 1.0(2) . . . . ? C2 C3 C4 C5 -1.2(2) . . . . ? C2 C3 C4 C8 -178.67(13) . . . . ? C3 C4 C5 C6 0.40(19) . . . . ? C8 C4 C5 C6 177.80(12) . . . . ? C4 C5 C6 C1 0.57(19) . . . . ? C2 C1 C6 C5 -0.77(19) . . . . ? C7 C1 C6 C5 179.55(11) . . . . ? N1 O1 C7 O2 -8.42(17) . . . . ? N1 O1 C7 C1 172.14(9) . . . . ? C2 C1 C7 O2 -179.32(13) . . . . ? C6 C1 C7 O2 0.35(19) . . . . ? C2 C1 C7 O1 0.10(17) . . . . ? C6 C1 C7 O1 179.77(10) . . . . ? C5 C4 C8 C9 19.65(18) . . . . ? C3 C4 C8 C9 -163.03(13) . . . . ? C5 C4 C8 C11A 140.52(14) . . . . ? C3 C4 C8 C11A -42.15(18) . . . . ? C5 C4 C8 C10 -100.44(15) . . . . ? C3 C4 C8 C10 76.89(16) . . . . ? C17 C12 C13 C14 -1.5(2) . . . . ? C18 C12 C13 C14 177.29(12) . . . . ? C12 C13 C14 C15 -0.3(2) . . . . ? C13 C14 C15 C16 1.76(19) . . . . ? C13 C14 C15 C19 179.99(12) . . . . ? C14 C15 C16 C17 -1.46(19) . . . . ? C19 C15 C16 C17 -179.68(12) . . . . ? C13 C12 C17 C16 1.8(2) . . . . ? C18 C12 C17 C16 -176.99(12) . . . . ? C15 C16 C17 C12 -0.3(2) . . . . ? N1 O3 C18 C12 -74.38(12) . . . . ? C17 C12 C18 O3 107.33(14) . . . . ? C13 C12 C18 O3 -71.43(16) . . . . ? C16 C15 C19 C22 91.85(17) . . . . ? C14 C15 C19 C22 -86.29(16) . . . . ? C16 C15 C19 C20 -29.11(19) . . . . ? C14 C15 C19 C20 152.75(15) . . . . ? C16 C15 C19 C21 -149.59(15) . . . . ? C14 C15 C19 C21 32.27(19) . . . . ? C28 C23 C24 C25 -1.71(18) . . . . ? C29 C23 C24 C25 179.86(11) . . . . ? C23 C24 C25 C26 2.05(19) . . . . ? C24 C25 C26 C27 -0.32(18) . . . . ? C24 C25 C26 C30 179.85(11) . . . . ? C25 C26 C27 C28 -1.73(18) . . . . ? C30 C26 C27 C28 178.10(12) . . . . ? C24 C23 C28 C27 -0.29(18) . . . . ? C29 C23 C28 C27 178.04(11) . . . . ? C26 C27 C28 C23 2.05(19) . . . . ? O3 N1 C29 O4 -134.01(12) . . . . ? O1 N1 C29 O4 -19.34(16) . . . . ? O3 N1 C29 C23 50.36(13) . . . . ? O1 N1 C29 C23 165.03(9) . . . . ? C28 C23 C29 O4 -141.90(14) . . . . ? C24 C23 C29 O4 36.46(18) . . . . ? C28 C23 C29 N1 33.53(16) . . . . ? C24 C23 C29 N1 -148.11(11) . . . . ? C27 C26 C30 C31 2.80(18) . . . . ? C25 C26 C30 C31 -177.39(12) . . . . ? C27 C26 C30 C32 -117.71(14) . . . . ? C25 C26 C30 C32 62.11(15) . . . . ? C27 C26 C30 C33 123.19(13) . . . . ? C25 C26 C30 C33 -56.99(16) . . . . ? _diffrn_measured_fraction_theta_max 0.976 _diffrn_reflns_theta_full 28.28 _diffrn_measured_fraction_theta_full 0.976 _refine_diff_density_max 0.238 _refine_diff_density_min -0.260 _refine_diff_density_rms 0.038