data_xl _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H27 N3 O10' _chemical_formula_weight 445.43 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' 'O' 'O' 0.0106 0.0060 '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' 'H' 'H' 0.0000 0.0000 '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 20.4218(2) _cell_length_b 12.1169(3) _cell_length_c 8.5406(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2113.36(16) _cell_formula_units_Z 4 _cell_measurement_temperature 293(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 1.400 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 944 _exptl_absorpt_coefficient_mu 0.115 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 4928 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0454 _diffrn_reflns_limit_h_min -26 _diffrn_reflns_limit_h_max 26 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 5.10 _diffrn_reflns_theta_max 27.90 _reflns_number_total 4928 _reflns_number_gt 4057 _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^)+(0.0569P)^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 SHELXL _refine_ls_extinction_coef 0.015(3) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.4(7) _refine_ls_number_reflns 4928 _refine_ls_number_parameters 289 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0536 _refine_ls_R_factor_gt 0.0391 _refine_ls_wR_factor_ref 0.0982 _refine_ls_wR_factor_gt 0.0928 _refine_ls_goodness_of_fit_ref 1.064 _refine_ls_restrained_S_all 1.064 _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 O10 O 0.49751(5) 0.75727(10) 0.12943(12) 0.0259(3) Uani 1 1 d . . . O12 O 0.38916(6) 0.74672(12) 0.06955(13) 0.0340(3) Uani 1 1 d . . . O15 O 0.36639(5) 0.78000(11) 0.49147(13) 0.0298(3) Uani 1 1 d . . . O17 O 0.26367(5) 0.77462(10) 0.38877(13) 0.0307(3) Uani 1 1 d . . . O21 O 0.64299(7) 0.90389(11) 0.84504(15) 0.0368(3) Uani 1 1 d . . . O41 O 0.65531(7) 0.52701(10) 0.86095(12) 0.0330(3) Uani 1 1 d . . . O71 O 0.58214(6) 0.56193(9) 0.35095(13) 0.0270(3) Uani 1 1 d . . . H71 H 0.5735 0.5211 0.4247 0.041 Uiso 1 1 calc R . . O81 O 0.47017(6) 0.63461(11) 0.51320(13) 0.0324(3) Uani 1 1 d . . . H81 H 0.4357 0.6625 0.5425 0.049 Uiso 1 1 calc R . . O101 O 0.56915(8) 0.97350(11) 0.59996(16) 0.0458(4) Uani 1 1 d . . . O102 O 0.61776(7) 0.90346(11) 0.39839(15) 0.0400(3) Uani 1 1 d . . . N3 N 0.64830(6) 0.71556(12) 0.86073(15) 0.0262(3) Uani 1 1 d . . . N5 N 0.61807(6) 0.60313(12) 0.64013(15) 0.0245(3) Uani 1 1 d . . . N101 N 0.59867(7) 0.89946(12) 0.53504(16) 0.0297(3) Uani 1 1 d . . . C1 C 0.61209(8) 0.79823(14) 0.62388(19) 0.0250(3) Uani 1 1 d . . . C2 C 0.63419(8) 0.80482(15) 0.77820(19) 0.0259(4) Uani 1 1 d . . . C4 C 0.64008(8) 0.61955(14) 0.78607(18) 0.0245(4) Uani 1 1 d . . . C6 C 0.60380(7) 0.69420(14) 0.55811(17) 0.0222(3) Uani 1 1 d . . . C7 C 0.57355(8) 0.67269(13) 0.39704(19) 0.0241(3) Uani 1 1 d . . . H7 H 0.5957 0.7200 0.3205 0.029 Uiso 1 1 calc R . . C8 C 0.50078(7) 0.70509(14) 0.40184(17) 0.0235(3) Uani 1 1 d . . . H8 H 0.4961 0.7824 0.4337 0.028 Uiso 1 1 calc R . . C9 C 0.46843(7) 0.68660(13) 0.24432(17) 0.0216(3) Uani 1 1 d . . . H9 H 0.4745 0.6095 0.2128 0.026 Uiso 1 1 calc R . . C11 C 0.45354(8) 0.75670(18) 0.0001(2) 0.0331(4) Uani 1 1 d . . . C13 C 0.39563(8) 0.71676(14) 0.23132(17) 0.0235(3) Uani 1 1 d . . . H13 H 0.3688 0.6514 0.2530 0.028 Uiso 1 1 calc R . . C14 C 0.37149(8) 0.81309(14) 0.3294(2) 0.0272(4) Uani 1 1 d . . . H14 H 0.4008 0.8767 0.3184 0.033 Uiso 1 1 calc R . . C16 C 0.29786(8) 0.77021(16) 0.53274(19) 0.0322(4) Uani 1 1 d . . . C18 C 0.30131(9) 0.84509(17) 0.2889(2) 0.0353(4) Uani 1 1 d . . . H18A H 0.2931 0.9223 0.3118 0.042 Uiso 1 1 calc R . . H18B H 0.2918 0.8311 0.1795 0.042 Uiso 1 1 calc R . . C22 C 0.65970(13) 0.90365(19) 1.0103(2) 0.0501(6) Uani 1 1 d . . . H22A H 0.7004 0.8654 1.0252 0.075 Uiso 1 1 calc R . . H22B H 0.6258 0.8671 1.0684 0.075 Uiso 1 1 calc R . . H22C H 0.6640 0.9783 1.0466 0.075 Uiso 1 1 calc R . . C42 C 0.67351(11) 0.53495(18) 1.0236(2) 0.0434(5) Uani 1 1 d . . . H42A H 0.6378 0.5658 1.0823 0.065 Uiso 1 1 calc R . . H42B H 0.7113 0.5816 1.0337 0.065 Uiso 1 1 calc R . . H42C H 0.6835 0.4627 1.0631 0.065 Uiso 1 1 calc R . . C111 C 0.46503(10) 0.6587(2) -0.1049(2) 0.0477(6) Uani 1 1 d . . . H11A H 0.4657 0.5925 -0.0432 0.072 Uiso 1 1 calc R . . H11B H 0.5062 0.6671 -0.1578 0.072 Uiso 1 1 calc R . . H11C H 0.4305 0.6541 -0.1808 0.072 Uiso 1 1 calc R . . C112 C 0.45855(11) 0.8655(2) -0.0828(3) 0.0594(7) Uani 1 1 d . . . H11D H 0.5013 0.8725 -0.1287 0.089 Uiso 1 1 calc R . . H11E H 0.4517 0.9243 -0.0093 0.089 Uiso 1 1 calc R . . H11F H 0.4259 0.8692 -0.1636 0.089 Uiso 1 1 calc R . . C161 C 0.27892(10) 0.8652(2) 0.6372(3) 0.0581(7) Uani 1 1 d . . . H16A H 0.2329 0.8616 0.6591 0.087 Uiso 1 1 calc R . . H16B H 0.2888 0.9335 0.5856 0.087 Uiso 1 1 calc R . . H16C H 0.3031 0.8608 0.7335 0.087 Uiso 1 1 calc R . . C162 C 0.28674(10) 0.6590(2) 0.6059(3) 0.0574(6) Uani 1 1 d . . . H16D H 0.3010 0.6023 0.5351 0.086 Uiso 1 1 calc R . . H16E H 0.2410 0.6496 0.6276 0.086 Uiso 1 1 calc R . . H16F H 0.3111 0.6539 0.7017 0.086 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 O10 0.0184(5) 0.0355(7) 0.0238(5) 0.0044(5) -0.0012(5) -0.0041(5) O12 0.0202(6) 0.0599(9) 0.0219(6) 0.0078(5) 0.0004(5) 0.0015(6) O15 0.0173(6) 0.0459(8) 0.0261(6) -0.0066(5) 0.0026(4) 0.0013(5) O17 0.0197(6) 0.0406(7) 0.0319(6) 0.0021(5) -0.0005(5) 0.0002(5) O21 0.0455(8) 0.0319(7) 0.0329(7) -0.0093(6) -0.0073(6) -0.0030(6) O41 0.0423(7) 0.0333(7) 0.0233(6) 0.0049(5) -0.0019(5) -0.0012(6) O71 0.0272(6) 0.0284(6) 0.0255(6) -0.0048(5) 0.0005(5) 0.0024(5) O81 0.0225(6) 0.0514(8) 0.0232(6) 0.0037(6) 0.0036(5) 0.0030(6) O101 0.0567(9) 0.0343(8) 0.0466(8) -0.0036(7) 0.0008(7) 0.0143(7) O102 0.0487(8) 0.0378(7) 0.0334(7) 0.0071(6) 0.0032(6) -0.0028(6) N3 0.0228(7) 0.0323(8) 0.0236(7) -0.0028(6) 0.0003(5) -0.0015(6) N5 0.0199(7) 0.0298(7) 0.0237(7) -0.0002(6) 0.0003(5) -0.0005(6) N101 0.0272(8) 0.0310(8) 0.0310(8) -0.0016(7) -0.0020(6) -0.0008(6) C1 0.0208(7) 0.0267(8) 0.0276(8) 0.0009(7) 0.0011(6) 0.0013(7) C2 0.0216(8) 0.0293(9) 0.0269(8) -0.0062(7) 0.0003(6) -0.0036(7) C4 0.0179(8) 0.0307(9) 0.0250(8) 0.0008(7) 0.0013(6) -0.0012(7) C6 0.0148(7) 0.0289(9) 0.0229(7) -0.0005(6) 0.0018(6) 0.0000(6) C7 0.0208(8) 0.0288(9) 0.0227(8) -0.0024(6) -0.0003(6) 0.0005(6) C8 0.0194(7) 0.0289(9) 0.0221(7) -0.0013(7) -0.0012(6) 0.0004(6) C9 0.0205(7) 0.0255(9) 0.0188(7) 0.0000(6) 0.0016(6) -0.0010(6) C11 0.0195(8) 0.0569(12) 0.0231(8) 0.0089(8) -0.0009(6) -0.0016(8) C13 0.0210(7) 0.0299(9) 0.0195(7) 0.0013(7) -0.0004(6) -0.0026(7) C14 0.0222(8) 0.0286(9) 0.0306(8) 0.0011(7) 0.0005(6) -0.0011(7) C16 0.0167(8) 0.0496(12) 0.0302(9) 0.0004(8) 0.0006(6) 0.0007(8) C18 0.0251(9) 0.0392(11) 0.0415(10) 0.0083(8) 0.0024(8) 0.0041(8) C22 0.0670(15) 0.0470(12) 0.0364(11) -0.0148(9) -0.0184(11) -0.0028(11) C42 0.0592(14) 0.0477(12) 0.0234(9) 0.0059(9) -0.0012(9) -0.0009(10) C111 0.0286(10) 0.0905(17) 0.0240(9) -0.0115(10) 0.0024(8) -0.0065(10) C112 0.0356(11) 0.0847(18) 0.0580(13) 0.0439(13) -0.0032(11) 0.0005(11) C161 0.0283(11) 0.0953(19) 0.0506(12) -0.0320(13) 0.0067(9) 0.0108(11) C162 0.0329(11) 0.0770(17) 0.0622(14) 0.0338(13) -0.0011(10) -0.0059(10) _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 O10 C11 1.423(2) . ? O10 C9 1.4313(18) . ? O12 C13 1.4345(18) . ? O12 C11 1.447(2) . ? O15 C14 1.445(2) . ? O15 C16 1.448(2) . ? O17 C16 1.4150(19) . ? O17 C18 1.431(2) . ? O21 C2 1.341(2) . ? O21 C22 1.452(2) . ? O41 C4 1.328(2) . ? O41 C42 1.441(2) . ? O71 C7 1.4096(19) . ? O81 C8 1.423(2) . ? O101 N101 1.2147(19) . ? O102 N101 1.2314(19) . ? N3 C2 1.323(2) . ? N3 C4 1.337(2) . ? N5 C6 1.339(2) . ? N5 C4 1.340(2) . ? N101 C1 1.468(2) . ? C1 C6 1.390(2) . ? C1 C2 1.395(2) . ? C6 C7 1.530(2) . ? C7 C8 1.538(2) . ? C8 C9 1.515(2) . ? C9 C13 1.535(2) . ? C11 C112 1.500(3) . ? C11 C111 1.506(3) . ? C13 C14 1.519(2) . ? C14 C18 1.524(2) . ? C16 C162 1.503(3) . ? C16 C161 1.506(3) . ? 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 O10 C9 105.50(11) . . ? C13 O12 C11 109.39(12) . . ? C14 O15 C16 109.00(12) . . ? C16 O17 C18 105.98(13) . . ? C2 O21 C22 116.32(16) . . ? C4 O41 C42 117.92(14) . . ? C2 N3 C4 115.46(13) . . ? C6 N5 C4 115.93(14) . . ? O101 N101 O102 124.11(16) . . ? O101 N101 C1 118.28(14) . . ? O102 N101 C1 117.61(14) . . ? C6 C1 C2 118.22(15) . . ? C6 C1 N101 121.73(14) . . ? C2 C1 N101 120.05(15) . . ? N3 C2 O21 118.41(14) . . ? N3 C2 C1 121.80(15) . . ? O21 C2 C1 119.77(16) . . ? O41 C4 N3 118.40(14) . . ? O41 C4 N5 113.65(15) . . ? N3 C4 N5 127.95(16) . . ? N5 C6 C1 120.61(13) . . ? N5 C6 C7 114.69(14) . . ? C1 C6 C7 124.52(15) . . ? O71 C7 C6 111.28(13) . . ? O71 C7 C8 111.77(13) . . ? C6 C7 C8 108.83(13) . . ? O81 C8 C9 108.25(12) . . ? O81 C8 C7 106.81(13) . . ? C9 C8 C7 111.09(13) . . ? O10 C9 C8 109.83(12) . . ? O10 C9 C13 102.11(12) . . ? C8 C9 C13 116.82(13) . . ? O10 C11 O12 104.82(12) . . ? O10 C11 C112 108.63(17) . . ? O12 C11 C112 109.20(16) . . ? O10 C11 C111 111.57(15) . . ? O12 C11 C111 108.64(15) . . ? C112 C11 C111 113.60(17) . . ? O12 C13 C14 107.85(13) . . ? O12 C13 C9 102.66(12) . . ? C14 C13 C9 117.23(13) . . ? O15 C14 C13 109.78(13) . . ? O15 C14 C18 102.70(13) . . ? C13 C14 C18 112.07(14) . . ? O17 C16 O15 105.21(12) . . ? O17 C16 C162 108.70(16) . . ? O15 C16 C162 108.70(15) . . ? O17 C16 C161 111.04(16) . . ? O15 C16 C161 109.26(15) . . ? C162 C16 C161 113.57(18) . . ? O17 C18 C14 102.61(14) . . ? _diffrn_measured_fraction_theta_max 0.979 _diffrn_reflns_theta_full 27.90 _diffrn_measured_fraction_theta_full 0.979 _refine_diff_density_max 0.261 _refine_diff_density_min -0.197 _refine_diff_density_rms 0.041