data_sttr _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H27 N O6' _chemical_formula_weight 425.47 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting ? _symmetry_space_group_name_H-M ? 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 10.154(2) _cell_length_b 11.161(2) _cell_length_c 19.700(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2232.6(8) _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 0.24 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.17 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.266 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 904 _exptl_absorpt_coefficient_mu 0.091 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.9785 _exptl_absorpt_correction_T_max 0.9847 _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 11754 _diffrn_reflns_av_R_equivalents 0.0581 _diffrn_reflns_av_sigmaI/netI 0.0516 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.82 _diffrn_reflns_theta_max 21.72 _reflns_number_total 2646 _reflns_number_gt 1960 _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^)+(0.0800P)^2^+0.7000P] 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(3) _refine_ls_number_reflns 2646 _refine_ls_number_parameters 286 _refine_ls_number_restraints 7 _refine_ls_R_factor_all 0.0950 _refine_ls_R_factor_gt 0.0696 _refine_ls_wR_factor_ref 0.1690 _refine_ls_wR_factor_gt 0.1569 _refine_ls_goodness_of_fit_ref 1.092 _refine_ls_restrained_S_all 1.094 _refine_ls_shift/su_max 0.128 _refine_ls_shift/su_mean 0.006 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 0.8458(4) 0.6054(4) 0.2335(3) 0.0799(14) Uani 1 1 d . . . H1 H 0.9022 0.5808 0.2072 0.096 Uiso 1 1 calc R . . O2 O 0.5611(4) 0.3061(3) 0.1432(2) 0.0718(13) Uani 1 1 d . . . H2 H 0.4828 0.2880 0.1418 0.086 Uiso 1 1 calc R . . O3 O 0.3098(4) 0.3538(4) 0.1428(3) 0.0834(14) Uani 1 1 d . . . O4 O 0.2414(4) 0.5411(4) 0.1639(3) 0.0826(14) Uani 1 1 d . . . H4 H 0.1699 0.5119 0.1539 0.050(17) Uiso 1 1 calc R . . O5 O 0.9863(3) 0.4735(4) 0.1531(2) 0.0723(12) Uani 1 1 d . . . O6 O 0.7963(5) 0.0657(5) 0.1707(3) 0.1163(19) Uani 1 1 d . . . N1 N 0.8022(4) 0.3638(4) 0.1737(2) 0.0630(13) Uani 1 1 d . . . H1A H 0.7761 0.2913 0.1795 0.076 Uiso 1 1 calc R . . C1 C 0.7258(6) 0.5666(6) 0.2130(3) 0.0665(18) Uani 1 1 d . . . C2 C 0.6192(7) 0.6438(6) 0.2242(4) 0.084(2) Uani 1 1 d . . . H2A H 0.6337 0.7192 0.2429 0.101 Uiso 1 1 calc R . . C3 C 0.4923(6) 0.6087(6) 0.2077(3) 0.076(2) Uani 1 1 d . . . H3 H 0.4229 0.6612 0.2157 0.091 Uiso 1 1 calc R . . C4 C 0.4658(5) 0.4965(5) 0.1792(3) 0.0546(15) Uani 1 1 d . . . C5 C 0.5743(5) 0.4195(5) 0.1696(3) 0.0573(16) Uani 1 1 d . . . C6 C 0.7025(5) 0.4541(5) 0.1852(3) 0.0546(15) Uani 1 1 d . . . C7 C 0.3338(5) 0.4568(7) 0.1611(3) 0.0670(17) Uani 1 1 d . . . C8 C 0.9263(6) 0.3749(6) 0.1558(3) 0.0608(16) Uani 1 1 d . . . C9 C 0.9983(6) 0.2603(6) 0.1368(4) 0.087(2) Uani 1 1 d . . . H9A H 0.9986 0.2070 0.1757 0.104 Uiso 1 1 calc R . . H9B H 1.0891 0.2797 0.1262 0.104 Uiso 1 1 calc R . . C10 C 0.9375(6) 0.1948(6) 0.0765(3) 0.0734(19) Uani 1 1 d . . . H10A H 0.9780 0.2240 0.0351 0.088 Uiso 1 1 calc R . . H10B H 0.8444 0.2138 0.0744 0.088 Uiso 1 1 calc R . . C11 C 0.9536(6) 0.0576(6) 0.0795(3) 0.0703(18) Uani 1 1 d . . . C12 C 0.8840(7) 0.0069(7) 0.1420(4) 0.088(2) Uani 1 1 d . . . C13 C 0.9243(9) -0.1095(8) 0.1664(5) 0.109(3) Uani 1 1 d . . . H13 H 0.8729 -0.1475 0.1990 0.131 Uiso 1 1 calc R . . C14 C 1.0312(11) -0.1639(6) 0.1443(5) 0.110(3) Uani 1 1 d . . . H14 H 1.0478 -0.2403 0.1610 0.132 Uiso 1 1 calc R . . C15 C 1.1281(7) -0.1140(5) 0.0948(4) 0.0713(18) Uani 1 1 d . . . C16 C 1.0998(5) 0.0214(5) 0.0831(3) 0.0655(17) Uani 1 1 d . . . H16 H 1.1342 0.0617 0.1236 0.079 Uiso 1 1 calc R . . C17 C 1.1874(7) 0.0654(7) 0.0243(4) 0.097(2) Uani 1 1 d . . . H17A H 1.2264 0.1420 0.0360 0.116 Uiso 1 1 calc R . . H17B H 1.1343 0.0761 -0.0162 0.116 Uiso 1 1 calc R . . C18 C 1.2969(10) -0.0273(10) 0.0105(5) 0.125(3) Uani 1 1 d . . . H18 H 1.3618 0.0070 -0.0208 0.150 Uiso 1 1 calc R . . C19 C 1.3624(9) -0.0582(9) 0.0759(6) 0.124(3) Uani 1 1 d D . . C20 C 1.2671(8) -0.1202(7) 0.1228(4) 0.091(2) Uani 1 1 d . . . H20A H 1.2699 -0.0824 0.1671 0.110 Uiso 1 1 calc R . . H20B H 1.2928 -0.2034 0.1282 0.110 Uiso 1 1 calc R . . C21 C 1.1333(10) -0.1825(7) 0.0280(5) 0.115(3) Uani 1 1 d . . . H21A H 1.1483 -0.2666 0.0378 0.137 Uiso 1 1 calc R . . H21B H 1.0484 -0.1759 0.0058 0.137 Uiso 1 1 calc R . . C22 C 1.2390(13) -0.1393(11) -0.0202(5) 0.152(5) Uani 1 1 d . . . H22A H 1.3065 -0.2000 -0.0257 0.182 Uiso 1 1 calc R . . H22B H 1.2013 -0.1219 -0.0644 0.182 Uiso 1 1 calc R . . C23 C 0.8799(8) 0.0047(6) 0.0165(4) 0.101(3) Uani 1 1 d . . . H23A H 0.9003 -0.0790 0.0123 0.121 Uiso 1 1 calc R . . H23B H 0.9075 0.0462 -0.0237 0.121 Uiso 1 1 calc R . . H23C H 0.7866 0.0144 0.0224 0.121 Uiso 1 1 calc R . . C24 C 1.4913(13) -0.0235(18) 0.0927(9) 0.292(12) Uani 1 1 d DU . . H24A H 1.5409 0.0214 0.0622 0.350 Uiso 1 1 calc R . . H24B H 1.5271 -0.0454 0.1344 0.350 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 0.052(3) 0.079(3) 0.109(4) -0.028(3) -0.011(2) -0.012(2) O2 0.047(2) 0.056(3) 0.112(4) -0.009(2) -0.014(3) -0.0108(19) O3 0.043(2) 0.068(3) 0.140(4) 0.012(3) -0.008(3) -0.004(2) O4 0.043(3) 0.076(3) 0.129(4) -0.003(3) 0.006(3) 0.008(2) O5 0.041(2) 0.057(3) 0.118(4) -0.002(3) -0.001(2) 0.007(2) O6 0.082(3) 0.137(5) 0.130(5) 0.004(4) 0.029(3) 0.000(3) N1 0.042(3) 0.053(3) 0.094(4) 0.004(3) -0.001(3) 0.005(2) C1 0.047(4) 0.080(5) 0.073(4) -0.012(4) -0.003(3) 0.002(4) C2 0.074(5) 0.081(5) 0.097(6) -0.036(4) 0.013(4) 0.012(4) C3 0.056(4) 0.081(5) 0.091(5) -0.023(4) 0.012(4) 0.017(4) C4 0.041(3) 0.058(4) 0.065(4) 0.000(3) -0.001(3) -0.001(3) C5 0.054(4) 0.054(4) 0.064(4) 0.010(3) -0.003(3) -0.018(3) C6 0.052(4) 0.054(4) 0.058(4) 0.003(3) -0.001(3) -0.008(3) C7 0.047(4) 0.077(4) 0.077(5) 0.003(4) 0.006(3) -0.007(4) C8 0.049(4) 0.049(4) 0.085(5) -0.005(3) -0.011(3) 0.010(3) C9 0.056(4) 0.070(4) 0.135(7) -0.003(4) -0.025(5) 0.002(4) C10 0.052(4) 0.082(5) 0.086(5) 0.000(4) -0.001(4) 0.011(3) C11 0.071(4) 0.062(4) 0.077(5) -0.006(4) -0.007(4) -0.012(3) C12 0.068(5) 0.100(6) 0.096(6) -0.002(5) 0.003(4) -0.013(4) C13 0.119(7) 0.084(6) 0.124(7) 0.021(6) 0.020(6) -0.029(5) C14 0.168(9) 0.043(4) 0.120(7) 0.019(5) 0.002(7) -0.010(5) C15 0.089(5) 0.045(4) 0.080(5) -0.001(3) 0.000(4) 0.007(3) C16 0.063(4) 0.059(4) 0.074(4) 0.003(3) 0.009(3) 0.014(3) C17 0.087(5) 0.075(5) 0.129(7) 0.030(5) 0.030(5) 0.026(4) C18 0.116(7) 0.147(9) 0.112(8) 0.026(7) 0.037(6) 0.036(7) C19 0.094(6) 0.134(8) 0.145(9) 0.026(7) 0.033(6) 0.043(6) C20 0.111(6) 0.070(5) 0.093(5) 0.005(4) 0.005(5) 0.033(5) C21 0.159(9) 0.072(5) 0.113(7) -0.023(5) -0.020(7) 0.030(6) C22 0.194(12) 0.163(11) 0.098(7) -0.030(8) 0.014(8) 0.075(10) C23 0.114(6) 0.099(6) 0.089(5) -0.022(5) -0.030(5) 0.006(5) C24 0.123(10) 0.48(3) 0.28(2) -0.09(2) 0.037(11) -0.071(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 O1 C1 1.355(7) . ? O2 C5 1.375(6) . ? O3 C7 1.230(7) . ? O4 C7 1.330(7) . ? O5 C8 1.259(7) . ? O6 C12 1.243(8) . ? N1 C8 1.314(7) . ? N1 C6 1.446(7) . ? C1 C6 1.391(8) . ? C1 C2 1.401(8) . ? C2 C3 1.385(9) . ? C3 C4 1.399(8) . ? C4 C5 1.410(7) . ? C4 C7 1.455(8) . ? C5 C6 1.392(7) . ? C8 C9 1.520(8) . ? C9 C10 1.527(9) . ? C10 C11 1.541(8) . ? C11 C12 1.527(10) . ? C11 C16 1.540(8) . ? C11 C23 1.565(9) . ? C12 C13 1.445(11) . ? C13 C14 1.317(11) . ? C14 C15 1.493(11) . ? C15 C20 1.517(9) . ? C15 C21 1.522(11) . ? C15 C16 1.555(8) . ? C16 C17 1.541(9) . ? C17 C18 1.543(11) . ? C18 C19 1.490(12) . ? C18 C22 1.508(13) . ? C19 C24 1.405(12) . ? C19 C20 1.507(11) . ? C21 C22 1.513(13) . ? 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 C8 N1 C6 130.4(5) . . ? O1 C1 C6 124.0(5) . . ? O1 C1 C2 116.9(6) . . ? C6 C1 C2 119.1(6) . . ? C3 C2 C1 120.5(6) . . ? C2 C3 C4 121.8(6) . . ? C3 C4 C5 116.7(5) . . ? C3 C4 C7 123.2(6) . . ? C5 C4 C7 120.1(5) . . ? O2 C5 C6 115.5(5) . . ? O2 C5 C4 122.4(5) . . ? C6 C5 C4 122.2(5) . . ? C1 C6 C5 119.8(6) . . ? C1 C6 N1 124.9(5) . . ? C5 C6 N1 115.3(5) . . ? O3 C7 O4 122.3(5) . . ? O3 C7 C4 122.6(6) . . ? O4 C7 C4 115.1(6) . . ? O5 C8 N1 123.9(5) . . ? O5 C8 C9 119.5(5) . . ? N1 C8 C9 116.7(6) . . ? C8 C9 C10 113.6(5) . . ? C9 C10 C11 113.7(5) . . ? C12 C11 C10 110.6(6) . . ? C12 C11 C16 108.2(6) . . ? C10 C11 C16 111.4(5) . . ? C12 C11 C23 106.1(5) . . ? C10 C11 C23 107.0(6) . . ? C16 C11 C23 113.5(6) . . ? O6 C12 C13 121.8(8) . . ? O6 C12 C11 120.1(7) . . ? C13 C12 C11 118.1(7) . . ? C14 C13 C12 122.5(8) . . ? C13 C14 C15 126.0(7) . . ? C14 C15 C20 111.0(6) . . ? C14 C15 C21 113.6(6) . . ? C20 C15 C21 105.0(6) . . ? C14 C15 C16 109.7(6) . . ? C20 C15 C16 105.7(6) . . ? C21 C15 C16 111.5(6) . . ? C11 C16 C17 116.0(5) . . ? C11 C16 C15 116.1(5) . . ? C17 C16 C15 108.3(5) . . ? C16 C17 C18 109.5(6) . . ? C19 C18 C22 109.2(9) . . ? C19 C18 C17 109.0(8) . . ? C22 C18 C17 110.2(9) . . ? C24 C19 C18 123.8(12) . . ? C24 C19 C20 125.5(11) . . ? C18 C19 C20 110.5(8) . . ? C19 C20 C15 110.7(7) . . ? C22 C21 C15 114.0(8) . . ? C18 C22 C21 106.8(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 O1 C1 C2 C3 -177.0(7) . . . . ? C6 C1 C2 C3 -0.1(10) . . . . ? C1 C2 C3 C4 -0.3(11) . . . . ? C2 C3 C4 C5 1.4(10) . . . . ? C2 C3 C4 C7 -179.9(7) . . . . ? C3 C4 C5 O2 178.9(6) . . . . ? C7 C4 C5 O2 0.1(8) . . . . ? C3 C4 C5 C6 -2.2(9) . . . . ? C7 C4 C5 C6 179.1(6) . . . . ? O1 C1 C6 C5 176.0(6) . . . . ? C2 C1 C6 C5 -0.6(9) . . . . ? O1 C1 C6 N1 -0.6(9) . . . . ? C2 C1 C6 N1 -177.3(6) . . . . ? O2 C5 C6 C1 -179.1(5) . . . . ? C4 C5 C6 C1 1.8(9) . . . . ? O2 C5 C6 N1 -2.2(8) . . . . ? C4 C5 C6 N1 178.8(5) . . . . ? C8 N1 C6 C1 -34.8(9) . . . . ? C8 N1 C6 C5 148.4(6) . . . . ? C3 C4 C7 O3 -172.2(6) . . . . ? C5 C4 C7 O3 6.5(9) . . . . ? C3 C4 C7 O4 9.7(9) . . . . ? C5 C4 C7 O4 -171.7(5) . . . . ? C6 N1 C8 O5 8.9(11) . . . . ? C6 N1 C8 C9 -170.3(6) . . . . ? O5 C8 C9 C10 -118.7(7) . . . . ? N1 C8 C9 C10 60.5(9) . . . . ? C8 C9 C10 C11 -148.6(6) . . . . ? C9 C10 C11 C12 61.9(7) . . . . ? C9 C10 C11 C16 -58.4(8) . . . . ? C9 C10 C11 C23 177.0(5) . . . . ? C10 C11 C12 O6 20.3(9) . . . . ? C16 C11 C12 O6 142.5(7) . . . . ? C23 C11 C12 O6 -95.4(7) . . . . ? C10 C11 C12 C13 -159.0(6) . . . . ? C16 C11 C12 C13 -36.8(8) . . . . ? C23 C11 C12 C13 85.3(7) . . . . ? O6 C12 C13 C14 -168.0(8) . . . . ? C11 C12 C13 C14 11.3(12) . . . . ? C12 C13 C14 C15 3.0(15) . . . . ? C13 C14 C15 C20 127.2(9) . . . . ? C13 C14 C15 C21 -114.8(10) . . . . ? C13 C14 C15 C16 10.8(12) . . . . ? C12 C11 C16 C17 -179.6(6) . . . . ? C10 C11 C16 C17 -57.9(8) . . . . ? C23 C11 C16 C17 63.0(7) . . . . ? C12 C11 C16 C15 51.5(7) . . . . ? C10 C11 C16 C15 173.2(6) . . . . ? C23 C11 C16 C15 -65.9(8) . . . . ? C14 C15 C16 C11 -39.1(8) . . . . ? C20 C15 C16 C11 -158.9(6) . . . . ? C21 C15 C16 C11 87.6(8) . . . . ? C14 C15 C16 C17 -171.6(6) . . . . ? C20 C15 C16 C17 68.6(7) . . . . ? C21 C15 C16 C17 -44.9(8) . . . . ? C11 C16 C17 C18 -147.7(7) . . . . ? C15 C16 C17 C18 -15.1(9) . . . . ? C16 C17 C18 C19 -49.8(10) . . . . ? C16 C17 C18 C22 70.0(10) . . . . ? C22 C18 C19 C24 129.9(13) . . . . ? C17 C18 C19 C24 -109.7(12) . . . . ? C22 C18 C19 C20 -55.6(10) . . . . ? C17 C18 C19 C20 64.9(10) . . . . ? C24 C19 C20 C15 164.8(12) . . . . ? C18 C19 C20 C15 -9.6(10) . . . . ? C14 C15 C20 C19 -174.1(7) . . . . ? C21 C15 C20 C19 62.8(8) . . . . ? C16 C15 C20 C19 -55.2(8) . . . . ? C14 C15 C21 C22 -175.2(7) . . . . ? C20 C15 C21 C22 -53.7(9) . . . . ? C16 C15 C21 C22 60.3(9) . . . . ? C19 C18 C22 C21 64.1(10) . . . . ? C17 C18 C22 C21 -55.6(11) . . . . ? C15 C21 C22 C18 -7.3(11) . . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 21.72 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.398 _refine_diff_density_min -0.154 _refine_diff_density_rms 0.048