# Electronic Supplementary Material (ESI) for Organic and Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_cambridge 0177 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_email 'tamura@ac.shoyaku.ac.jp ' _publ_contact_author_name 'Tamura, Osamu' loop_ _publ_author_name 'Kenichi Kobayashi' 'Iwao Okamoto' 'Nobuyoshi Morita' 'Tamiko Kiyotani' 'Osamu Tamura' data_100910c3 _database_code_depnum_ccdc_archive 'CCDC 823955' #TrackingRef 'compound-20.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; (6R)-2,6-anhydro-4-O-[tert-butyl(dimethyl)silyl]-3-deoxy -1-(methoxyamino)-3-(methoxycarbonyl)-5-O-(methoxymethyl) -5-C-methyl-6-pentyl-L-reythro-hex-2-enose ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C23 H43 N O8 Si' _chemical_formula_sum 'C23 H43 N O8 Si' _chemical_formula_weight 489.67 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Si Si 0.2541 0.3302 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' _symmetry_space_group_name_Hall 'P 2ac 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 9.0593(3) _cell_length_b 15.3579(5) _cell_length_c 19.9706(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2778.55(15) _cell_formula_units_Z 4 _cell_measurement_temperature 100 _cell_measurement_reflns_used 20116 _cell_measurement_theta_min 3.63 _cell_measurement_theta_max 68.34 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.21 _exptl_crystal_size_mid 0.07 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.171 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1064 _exptl_absorpt_coefficient_mu 1.104 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7821 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details ; Higashi, T. (1995). Program for Absorption Correction. Rigaku Corporation, Tokyo, Japan. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 1.54187 _diffrn_radiation_type CuK\a _diffrn_radiation_source ? _diffrn_radiation_monochromator ? _diffrn_measurement_device_type 'Rigaku VariMax RAPID' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 10.0 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 29436 _diffrn_reflns_av_R_equivalents 0.1034 _diffrn_reflns_av_sigmaI/netI 0.0843 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 3.63 _diffrn_reflns_theta_max 68.23 _reflns_number_total 5051 _reflns_number_gt 3983 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'PROCESS-AUTO (Rigaku, 1998)' _computing_cell_refinement 'PROCESS-AUTO (Rigaku, 1998)' _computing_data_reduction 'PROCESS-AUTO (Rigaku, 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Yadokari-XG 2009 (Wakita Nemoto et al., 2009)' _computing_publication_material ; Yadokari-XG 2009 (Wakita,Nemoto et al., 2009) ; _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^)+(0.0498P)^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 constr _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 -0.04(4) _refine_ls_number_reflns 5051 _refine_ls_number_parameters 308 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0713 _refine_ls_R_factor_gt 0.0569 _refine_ls_wR_factor_ref 0.1255 _refine_ls_wR_factor_gt 0.1155 _refine_ls_goodness_of_fit_ref 1.018 _refine_ls_restrained_S_all 1.018 _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 Si1 Si 0.77610(11) 0.87556(6) 0.78623(4) 0.0353(2) Uani 1 1 d . . . O1 O 0.6751(2) 0.91867(13) 0.52221(9) 0.0278(5) Uani 1 1 d . . . O2 O 0.8336(2) 0.76904(14) 0.46104(10) 0.0328(5) Uani 1 1 d . . . O3 O 0.6053(3) 0.66878(14) 0.41801(10) 0.0395(6) Uani 1 1 d . . . O4 O 0.6090(3) 0.69653(15) 0.68369(11) 0.0529(7) Uani 1 1 d . . . O5 O 0.7174(3) 0.66497(14) 0.58569(11) 0.0392(6) Uani 1 1 d . . . O6 O 0.7627(2) 0.89101(13) 0.70414(9) 0.0290(5) Uani 1 1 d . . . O7 O 0.5882(3) 1.02706(13) 0.68385(10) 0.0327(5) Uani 1 1 d . . . O8 O 0.6030(3) 1.16632(15) 0.63386(11) 0.0435(6) Uani 1 1 d . . . N1 N 0.5890(3) 0.73633(17) 0.46395(12) 0.0326(6) Uani 1 1 d . . . H1 H 0.5009 0.7526 0.4777 0.039 Uiso 1 1 calc R . . C1 C 0.7108(4) 0.7757(2) 0.48649(14) 0.0285(7) Uani 1 1 d . . . C2 C 0.6824(3) 0.8361(2) 0.54487(15) 0.0255(7) Uani 1 1 d . . . C3 C 0.6669(3) 0.81186(19) 0.60960(14) 0.0266(7) Uani 1 1 d . . . C4 C 0.6349(3) 0.8778(2) 0.66414(14) 0.0283(7) Uani 1 1 d . . . H41 H 0.5546 0.8542 0.6933 0.034 Uiso 1 1 calc R . . C5 C 0.5797(4) 0.9621(2) 0.63143(14) 0.0274(7) Uani 1 1 d . . . C6 C 0.6797(3) 0.9887(2) 0.57244(14) 0.0270(7) Uani 1 1 d . . . H61 H 0.6356 1.0418 0.5515 0.032 Uiso 1 1 calc R . . C7 C 0.5992(5) 0.7026(2) 0.35068(16) 0.0500(10) Uani 1 1 d . . . H71 H 0.5070 0.7349 0.3445 0.075 Uiso 1 1 calc R . . H72 H 0.6032 0.6542 0.3187 0.075 Uiso 1 1 calc R . . H73 H 0.6833 0.7415 0.3431 0.075 Uiso 1 1 calc R . . C8 C 0.6606(4) 0.7203(2) 0.63081(16) 0.0356(8) Uani 1 1 d . . . C9 C 0.6801(5) 0.5736(2) 0.5955(2) 0.0528(11) Uani 1 1 d . . . H91 H 0.7117 0.5552 0.6403 0.079 Uiso 1 1 calc R . . H92 H 0.7305 0.5382 0.5617 0.079 Uiso 1 1 calc R . . H93 H 0.5731 0.5659 0.5913 0.079 Uiso 1 1 calc R . . C10 C 0.8765(5) 0.7717(2) 0.80088(17) 0.0529(11) Uani 1 1 d . . . H101 H 0.8783 0.7590 0.8490 0.079 Uiso 1 1 calc R . . H102 H 0.9778 0.7770 0.7842 0.079 Uiso 1 1 calc R . . H103 H 0.8262 0.7243 0.7772 0.079 Uiso 1 1 calc R . . C11 C 0.5904(4) 0.8688(3) 0.82524(16) 0.0515(10) Uani 1 1 d . . . H111 H 0.5313 0.9191 0.8114 0.077 Uiso 1 1 calc R . . H112 H 0.6005 0.8687 0.8741 0.077 Uiso 1 1 calc R . . H113 H 0.5415 0.8151 0.8108 0.077 Uiso 1 1 calc R . . C12 C 0.8830(4) 0.9695(2) 0.82214(16) 0.0433(9) Uani 1 1 d . . . C13 C 0.9445(5) 0.9435(3) 0.89199(16) 0.0507(10) Uani 1 1 d . . . H131 H 0.8632 0.9235 0.9205 0.076 Uiso 1 1 calc R . . H132 H 0.9922 0.9940 0.9127 0.076 Uiso 1 1 calc R . . H133 H 1.0167 0.8965 0.8868 0.076 Uiso 1 1 calc R . . C14 C 1.0138(5) 0.9940(3) 0.77732(18) 0.0657(13) Uani 1 1 d . . . H141 H 1.0846 0.9458 0.7763 0.098 Uiso 1 1 calc R . . H142 H 1.0620 1.0462 0.7951 0.098 Uiso 1 1 calc R . . H143 H 0.9784 1.0056 0.7318 0.098 Uiso 1 1 calc R . . C15 C 0.7841(6) 1.0486(2) 0.8315(2) 0.0702(14) Uani 1 1 d . . . H151 H 0.7410 1.0651 0.7883 0.105 Uiso 1 1 calc R . . H152 H 0.8427 1.0972 0.8490 0.105 Uiso 1 1 calc R . . H153 H 0.7051 1.0345 0.8632 0.105 Uiso 1 1 calc R . . C16 C 0.4216(4) 0.9480(2) 0.60795(16) 0.0376(8) Uani 1 1 d . . . H161 H 0.3554 0.9475 0.6468 0.056 Uiso 1 1 calc R . . H162 H 0.4147 0.8921 0.5844 0.056 Uiso 1 1 calc R . . H163 H 0.3931 0.9952 0.5776 0.056 Uiso 1 1 calc R . . C17 C 0.5190(4) 1.1092(2) 0.67267(18) 0.0421(9) Uani 1 1 d . . . H171 H 0.4230 1.0995 0.6502 0.051 Uiso 1 1 calc R . . H172 H 0.4988 1.1369 0.7165 0.051 Uiso 1 1 calc R . . C18 C 0.7191(5) 1.2059(2) 0.67004(19) 0.0526(10) Uani 1 1 d . . . H181 H 0.7884 1.1610 0.6853 0.079 Uiso 1 1 calc R . . H182 H 0.6786 1.2367 0.7089 0.079 Uiso 1 1 calc R . . H183 H 0.7709 1.2473 0.6411 0.079 Uiso 1 1 calc R . . C19 C 0.8401(3) 1.0088(2) 0.58779(14) 0.0283(7) Uani 1 1 d . . . H191 H 0.8949 0.9536 0.5938 0.034 Uiso 1 1 calc R . . H192 H 0.8460 1.0419 0.6303 0.034 Uiso 1 1 calc R . . C20 C 0.9123(4) 1.0617(2) 0.53206(15) 0.0306(7) Uani 1 1 d . . . H201 H 0.9106 1.0270 0.4903 0.037 Uiso 1 1 calc R . . H202 H 0.8532 1.1150 0.5243 0.037 Uiso 1 1 calc R . . C21 C 1.0700(4) 1.0877(2) 0.54707(15) 0.0313(8) Uani 1 1 d . . . H211 H 1.1309 1.0344 0.5503 0.038 Uiso 1 1 calc R . . H212 H 1.0728 1.1170 0.5912 0.038 Uiso 1 1 calc R . . C22 C 1.1384(4) 1.1481(2) 0.49484(17) 0.0360(8) Uani 1 1 d . . . H221 H 1.1394 1.1179 0.4511 0.043 Uiso 1 1 calc R . . H222 H 1.0753 1.2004 0.4902 0.043 Uiso 1 1 calc R . . C23 C 1.2944(4) 1.1770(2) 0.51150(17) 0.0422(9) Uani 1 1 d . . . H231 H 1.2948 1.2068 0.5549 0.063 Uiso 1 1 calc R . . H232 H 1.3300 1.2168 0.4768 0.063 Uiso 1 1 calc R . . H233 H 1.3592 1.1259 0.5136 0.063 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 Si1 0.0383(5) 0.0447(5) 0.0228(4) 0.0003(4) 0.0012(4) 0.0014(5) O1 0.0331(13) 0.0297(11) 0.0206(10) -0.0008(9) -0.0016(9) -0.0019(10) O2 0.0261(13) 0.0422(13) 0.0302(11) -0.0072(10) 0.0053(10) -0.0014(11) O3 0.0426(14) 0.0444(14) 0.0316(12) -0.0122(11) 0.0004(11) -0.0028(12) O4 0.077(2) 0.0440(15) 0.0377(13) 0.0048(12) 0.0133(14) -0.0120(15) O5 0.0529(15) 0.0291(12) 0.0354(12) -0.0030(10) 0.0018(12) 0.0035(11) O6 0.0295(12) 0.0354(12) 0.0221(10) -0.0005(9) 0.0008(9) -0.0024(10) O7 0.0368(14) 0.0352(13) 0.0262(11) -0.0058(10) 0.0020(10) 0.0063(11) O8 0.0550(17) 0.0378(13) 0.0377(13) -0.0001(11) -0.0070(13) 0.0030(13) N1 0.0278(16) 0.0366(15) 0.0334(14) -0.0132(12) -0.0021(13) 0.0021(13) C1 0.0312(18) 0.0337(17) 0.0206(15) 0.0019(13) 0.0031(14) 0.0040(15) C2 0.0164(16) 0.0312(17) 0.0288(15) -0.0014(14) 0.0009(13) -0.0004(13) C3 0.0262(17) 0.0297(17) 0.0238(15) -0.0021(13) -0.0013(13) -0.0031(14) C4 0.0287(18) 0.0326(17) 0.0236(15) 0.0014(14) 0.0049(13) -0.0053(15) C5 0.0252(17) 0.0321(17) 0.0247(15) -0.0059(13) -0.0022(14) -0.0013(14) C6 0.0324(18) 0.0259(16) 0.0226(15) -0.0021(13) 0.0024(13) 0.0015(14) C7 0.059(3) 0.061(2) 0.0300(18) -0.0102(18) -0.0031(19) 0.002(2) C8 0.039(2) 0.0368(19) 0.0306(17) 0.0012(15) -0.0024(16) -0.0032(16) C9 0.067(3) 0.032(2) 0.060(2) -0.0022(19) -0.011(2) -0.001(2) C10 0.070(3) 0.050(2) 0.039(2) 0.0109(18) -0.003(2) 0.009(2) C11 0.049(2) 0.074(3) 0.0313(18) -0.003(2) 0.0066(18) -0.005(2) C12 0.051(2) 0.050(2) 0.0295(18) -0.0008(17) -0.0084(17) -0.0001(19) C13 0.057(3) 0.068(3) 0.0264(18) -0.0042(18) -0.0064(18) 0.001(2) C14 0.070(3) 0.093(3) 0.034(2) -0.001(2) -0.010(2) -0.040(3) C15 0.097(4) 0.048(2) 0.066(3) -0.010(2) -0.037(3) 0.008(2) C16 0.031(2) 0.043(2) 0.0387(19) -0.0044(16) 0.0040(17) 0.0015(16) C17 0.039(2) 0.043(2) 0.044(2) -0.0118(18) 0.0047(17) 0.0099(18) C18 0.060(3) 0.042(2) 0.056(2) -0.0054(19) -0.007(2) -0.004(2) C19 0.0270(17) 0.0335(17) 0.0243(15) -0.0006(14) -0.0013(13) -0.0003(15) C20 0.0266(18) 0.0344(18) 0.0310(17) 0.0024(14) 0.0003(15) 0.0034(15) C21 0.0278(18) 0.0404(19) 0.0258(15) -0.0024(14) 0.0001(14) -0.0012(16) C22 0.032(2) 0.0349(18) 0.0409(19) 0.0041(15) 0.0021(16) -0.0030(16) C23 0.041(2) 0.049(2) 0.0372(19) 0.0009(17) 0.0074(17) -0.0078(18) _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 Si1 O6 1.661(2) . ? Si1 C11 1.857(4) . ? Si1 C10 1.859(4) . ? Si1 C12 1.880(4) . ? O1 C2 1.348(3) . ? O1 C6 1.471(3) . ? O2 C1 1.227(4) . ? O3 N1 1.393(3) . ? O3 C7 1.442(4) . ? O4 C8 1.212(4) . ? O5 C8 1.341(4) . ? O5 C9 1.457(4) . ? O6 C4 1.421(3) . ? O7 C17 1.427(4) . ? O7 C5 1.448(3) . ? O8 C17 1.396(4) . ? O8 C18 1.414(4) . ? N1 C1 1.337(4) . ? N1 H1 0.8800 . ? C1 C2 1.512(4) . ? C2 C3 1.353(4) . ? C3 C8 1.469(4) . ? C3 C4 1.515(4) . ? C4 C5 1.534(4) . ? C4 H41 1.0000 . ? C5 C16 1.523(5) . ? C5 C6 1.541(4) . ? C6 C19 1.517(4) . ? C6 H61 1.0000 . ? C7 H71 0.9800 . ? C7 H72 0.9800 . ? C7 H73 0.9800 . ? C9 H91 0.9800 . ? C9 H92 0.9800 . ? C9 H93 0.9800 . ? C10 H101 0.9800 . ? C10 H102 0.9800 . ? C10 H103 0.9800 . ? C11 H111 0.9800 . ? C11 H112 0.9800 . ? C11 H113 0.9800 . ? C12 C15 1.520(5) . ? C12 C14 1.532(5) . ? C12 C13 1.554(5) . ? C13 H131 0.9800 . ? C13 H132 0.9800 . ? C13 H133 0.9800 . ? C14 H141 0.9800 . ? C14 H142 0.9800 . ? C14 H143 0.9800 . ? C15 H151 0.9800 . ? C15 H152 0.9800 . ? C15 H153 0.9800 . ? C16 H161 0.9800 . ? C16 H162 0.9800 . ? C16 H163 0.9800 . ? C17 H171 0.9900 . ? C17 H172 0.9900 . ? C18 H181 0.9800 . ? C18 H182 0.9800 . ? C18 H183 0.9800 . ? C19 C20 1.525(4) . ? C19 H191 0.9900 . ? C19 H192 0.9900 . ? C20 C21 1.514(5) . ? C20 H201 0.9900 . ? C20 H202 0.9900 . ? C21 C22 1.528(4) . ? C21 H211 0.9900 . ? C21 H212 0.9900 . ? C22 C23 1.518(5) . ? C22 H221 0.9900 . ? C22 H222 0.9900 . ? C23 H231 0.9800 . ? C23 H232 0.9800 . ? C23 H233 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 O6 Si1 C11 110.84(14) . . ? O6 Si1 C10 108.29(14) . . ? C11 Si1 C10 109.22(19) . . ? O6 Si1 C12 107.73(13) . . ? C11 Si1 C12 110.44(18) . . ? C10 Si1 C12 110.29(18) . . ? C2 O1 C6 117.2(2) . . ? N1 O3 C7 110.0(2) . . ? C8 O5 C9 115.5(3) . . ? C4 O6 Si1 126.46(17) . . ? C17 O7 C5 118.2(2) . . ? C17 O8 C18 113.1(3) . . ? C1 N1 O3 118.1(3) . . ? C1 N1 H1 121.0 . . ? O3 N1 H1 121.0 . . ? O2 C1 N1 124.8(3) . . ? O2 C1 C2 121.7(3) . . ? N1 C1 C2 113.4(3) . . ? O1 C2 C3 125.1(3) . . ? O1 C2 C1 109.0(2) . . ? C3 C2 C1 125.9(3) . . ? C2 C3 C8 122.9(3) . . ? C2 C3 C4 121.5(3) . . ? C8 C3 C4 115.1(3) . . ? O6 C4 C3 110.1(2) . . ? O6 C4 C5 112.6(2) . . ? C3 C4 C5 108.7(2) . . ? O6 C4 H41 108.5 . . ? C3 C4 H41 108.5 . . ? C5 C4 H41 108.5 . . ? O7 C5 C16 111.8(3) . . ? O7 C5 C4 104.9(2) . . ? C16 C5 C4 108.5(3) . . ? O7 C5 C6 109.8(2) . . ? C16 C5 C6 110.8(2) . . ? C4 C5 C6 110.9(3) . . ? O1 C6 C19 108.3(2) . . ? O1 C6 C5 108.2(2) . . ? C19 C6 C5 117.6(2) . . ? O1 C6 H61 107.5 . . ? C19 C6 H61 107.5 . . ? C5 C6 H61 107.5 . . ? O3 C7 H71 109.5 . . ? O3 C7 H72 109.5 . . ? H71 C7 H72 109.5 . . ? O3 C7 H73 109.5 . . ? H71 C7 H73 109.5 . . ? H72 C7 H73 109.5 . . ? O4 C8 O5 122.8(3) . . ? O4 C8 C3 123.7(3) . . ? O5 C8 C3 113.5(3) . . ? O5 C9 H91 109.5 . . ? O5 C9 H92 109.5 . . ? H91 C9 H92 109.5 . . ? O5 C9 H93 109.5 . . ? H91 C9 H93 109.5 . . ? H92 C9 H93 109.5 . . ? Si1 C10 H101 109.5 . . ? Si1 C10 H102 109.5 . . ? H101 C10 H102 109.5 . . ? Si1 C10 H103 109.5 . . ? H101 C10 H103 109.5 . . ? H102 C10 H103 109.5 . . ? Si1 C11 H111 109.5 . . ? Si1 C11 H112 109.5 . . ? H111 C11 H112 109.5 . . ? Si1 C11 H113 109.5 . . ? H111 C11 H113 109.5 . . ? H112 C11 H113 109.5 . . ? C15 C12 C14 109.4(4) . . ? C15 C12 C13 107.8(3) . . ? C14 C12 C13 108.1(3) . . ? C15 C12 Si1 110.9(3) . . ? C14 C12 Si1 111.3(2) . . ? C13 C12 Si1 109.2(2) . . ? C12 C13 H131 109.5 . . ? C12 C13 H132 109.5 . . ? H131 C13 H132 109.5 . . ? C12 C13 H133 109.5 . . ? H131 C13 H133 109.5 . . ? H132 C13 H133 109.5 . . ? C12 C14 H141 109.5 . . ? C12 C14 H142 109.5 . . ? H141 C14 H142 109.5 . . ? C12 C14 H143 109.5 . . ? H141 C14 H143 109.5 . . ? H142 C14 H143 109.5 . . ? C12 C15 H151 109.5 . . ? C12 C15 H152 109.5 . . ? H151 C15 H152 109.5 . . ? C12 C15 H153 109.5 . . ? H151 C15 H153 109.5 . . ? H152 C15 H153 109.5 . . ? C5 C16 H161 109.5 . . ? C5 C16 H162 109.5 . . ? H161 C16 H162 109.5 . . ? C5 C16 H163 109.5 . . ? H161 C16 H163 109.5 . . ? H162 C16 H163 109.5 . . ? O8 C17 O7 113.8(3) . . ? O8 C17 H171 108.8 . . ? O7 C17 H171 108.8 . . ? O8 C17 H172 108.8 . . ? O7 C17 H172 108.8 . . ? H171 C17 H172 107.7 . . ? O8 C18 H181 109.5 . . ? O8 C18 H182 109.5 . . ? H181 C18 H182 109.5 . . ? O8 C18 H183 109.5 . . ? H181 C18 H183 109.5 . . ? H182 C18 H183 109.5 . . ? C6 C19 C20 111.8(2) . . ? C6 C19 H191 109.2 . . ? C20 C19 H191 109.2 . . ? C6 C19 H192 109.2 . . ? C20 C19 H192 109.2 . . ? H191 C19 H192 107.9 . . ? C21 C20 C19 113.6(2) . . ? C21 C20 H201 108.8 . . ? C19 C20 H201 108.8 . . ? C21 C20 H202 108.8 . . ? C19 C20 H202 108.8 . . ? H201 C20 H202 107.7 . . ? C20 C21 C22 114.1(3) . . ? C20 C21 H211 108.7 . . ? C22 C21 H211 108.7 . . ? C20 C21 H212 108.7 . . ? C22 C21 H212 108.7 . . ? H211 C21 H212 107.6 . . ? C23 C22 C21 113.9(3) . . ? C23 C22 H221 108.8 . . ? C21 C22 H221 108.8 . . ? C23 C22 H222 108.8 . . ? C21 C22 H222 108.8 . . ? H221 C22 H222 107.7 . . ? C22 C23 H231 109.5 . . ? C22 C23 H232 109.5 . . ? H231 C23 H232 109.5 . . ? C22 C23 H233 109.5 . . ? H231 C23 H233 109.5 . . ? H232 C23 H233 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 C11 Si1 O6 C4 -16.3(3) . . . . ? C10 Si1 O6 C4 103.5(3) . . . . ? C12 Si1 O6 C4 -137.3(3) . . . . ? C7 O3 N1 C1 -91.5(3) . . . . ? O3 N1 C1 O2 14.7(5) . . . . ? O3 N1 C1 C2 -169.5(2) . . . . ? C6 O1 C2 C3 12.6(4) . . . . ? C6 O1 C2 C1 -167.3(2) . . . . ? O2 C1 C2 O1 76.6(4) . . . . ? N1 C1 C2 O1 -99.5(3) . . . . ? O2 C1 C2 C3 -103.4(4) . . . . ? N1 C1 C2 C3 80.6(4) . . . . ? O1 C2 C3 C8 173.5(3) . . . . ? C1 C2 C3 C8 -6.5(5) . . . . ? O1 C2 C3 C4 1.6(5) . . . . ? C1 C2 C3 C4 -178.5(3) . . . . ? Si1 O6 C4 C3 -121.6(2) . . . . ? Si1 O6 C4 C5 116.9(2) . . . . ? C2 C3 C4 O6 -106.9(3) . . . . ? C8 C3 C4 O6 80.5(3) . . . . ? C2 C3 C4 C5 16.8(4) . . . . ? C8 C3 C4 C5 -155.7(3) . . . . ? C17 O7 C5 C16 -51.4(3) . . . . ? C17 O7 C5 C4 -168.7(3) . . . . ? C17 O7 C5 C6 72.0(3) . . . . ? O6 C4 C5 O7 -43.6(3) . . . . ? C3 C4 C5 O7 -165.8(2) . . . . ? O6 C4 C5 C16 -163.1(2) . . . . ? C3 C4 C5 C16 74.6(3) . . . . ? O6 C4 C5 C6 75.0(3) . . . . ? C3 C4 C5 C6 -47.3(3) . . . . ? C2 O1 C6 C19 85.5(3) . . . . ? C2 O1 C6 C5 -42.9(3) . . . . ? O7 C5 C6 O1 176.6(2) . . . . ? C16 C5 C6 O1 -59.4(3) . . . . ? C4 C5 C6 O1 61.1(3) . . . . ? O7 C5 C6 C19 53.6(3) . . . . ? C16 C5 C6 C19 177.6(3) . . . . ? C4 C5 C6 C19 -61.8(3) . . . . ? C9 O5 C8 O4 15.2(5) . . . . ? C9 O5 C8 C3 -164.6(3) . . . . ? C2 C3 C8 O4 -159.7(4) . . . . ? C4 C3 C8 O4 12.8(5) . . . . ? C2 C3 C8 O5 20.1(5) . . . . ? C4 C3 C8 O5 -167.5(3) . . . . ? O6 Si1 C12 C15 80.6(3) . . . . ? C11 Si1 C12 C15 -40.5(3) . . . . ? C10 Si1 C12 C15 -161.4(3) . . . . ? O6 Si1 C12 C14 -41.4(3) . . . . ? C11 Si1 C12 C14 -162.6(3) . . . . ? C10 Si1 C12 C14 76.6(3) . . . . ? O6 Si1 C12 C13 -160.6(2) . . . . ? C11 Si1 C12 C13 78.2(3) . . . . ? C10 Si1 C12 C13 -42.6(3) . . . . ? C18 O8 C17 O7 -77.3(4) . . . . ? C5 O7 C17 O8 -80.7(3) . . . . ? O1 C6 C19 C20 76.0(3) . . . . ? C5 C6 C19 C20 -161.2(3) . . . . ? C6 C19 C20 C21 176.7(3) . . . . ? C19 C20 C21 C22 -174.3(3) . . . . ? C20 C21 C22 C23 177.7(3) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1 O2 0.88 1.98 2.758(3) 147.3 3_466 _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 68.23 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.338 _refine_diff_density_min -0.371 _refine_diff_density_rms 0.051 _publ_section_references ; Wakita, K. (2001). Yadokari-XG. Software for Crystal Structure Analyses. \nRelease of Software (Yadokari-XG 2009) for Crystal Structure Analyses, \nKabuto, C., Akine, S., Nemoto, T. & Kwon, E. (2009). \nJ. Cryst. Soc. Jpn. 51, 218-224. ; _chemical_absolute_configuration ad