Supplementary Material (ESI) for Chemical Communications This journal is © The Royal Society of Chemistry 2002 data_global _journal_coden_Cambridge 182 loop_ _publ_author_name 'Wong, Henry N. C.' 'Lee, Hing Ken' _publ_contact_author_name 'Prof Henry N. C. Wong' _publ_contact_author_address ; Department of Chemistry Institute of Chinese Medicine Central Laboratory of the Institute for Drug Discovery and Synthesis Chinese University of Hong Kong Shatin New Territories HONG KONG ; _publ_contact_author_email 'HNCWONG@CUHK.EDU.HK' _publ_requested_journal 'Chemical Communications' _publ_section_title ; An Enantioselective Synthetic Pathway Towards Plakortones ; data_ken588 _database_code_CSD 188284 _audit_creation_method SHELXL-97 _chemical_name_systematic ; (1R,5S,8R)-3-oxo-1-ethyl-5-(tert-butydimethylsiloxy)methyl-8-hydroxy-2,6- dioxabicyclo[3.3.0]ocatne ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H28 O5 Si' _chemical_formula_weight 316.46 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' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Si' 'Si' 0.0817 0.0704 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) 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 7.6575(9) _cell_length_b 10.613(1) _cell_length_c 22.158(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1800.8(4) _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 block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.62 _exptl_crystal_size_mid 0.44 _exptl_crystal_size_min 0.42 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.167 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 688 _exptl_absorpt_coefficient_mu 0.147 _exptl_absorpt_correction_type 'empirical' _exptl_absorpt_correction_T_min 0.7061 _exptl_absorpt_correction_T_max 1.0000 _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 'CCD area detector' _diffrn_measurement_method 'phi ang omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12571 _diffrn_reflns_av_R_equivalents 0.0286 _diffrn_reflns_av_sigmaI/netI 0.0324 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.84 _diffrn_reflns_theta_max 28.01 _reflns_number_total 4321 _reflns_number_gt 3254 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0547P)^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(11) _refine_ls_number_reflns 4321 _refine_ls_number_parameters 190 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0535 _refine_ls_R_factor_gt 0.0365 _refine_ls_wR_factor_ref 0.0955 _refine_ls_wR_factor_gt 0.0866 _refine_ls_goodness_of_fit_ref 0.964 _refine_ls_restrained_S_all 0.964 _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 Si1 Si 0.21494(7) 0.79537(4) 0.82304(2) 0.04865(14) Uani 1 1 d . . . O1 O 0.44311(14) 0.37700(10) 0.96734(6) 0.0480(3) Uani 1 1 d . . . O2 O 0.73226(15) 0.38005(12) 0.96409(7) 0.0677(4) Uani 1 1 d . . . O3 O 0.37451(17) 0.62173(12) 1.02796(5) 0.0561(3) Uani 1 1 d . . . O4 O 0.01897(17) 0.51518(13) 1.00550(8) 0.0694(4) Uani 1 1 d . . . H4A H -0.0545 0.4650 0.9934 0.104 Uiso 1 1 calc R . . O5 O 0.31511(17) 0.69923(11) 0.87005(5) 0.0505(3) Uani 1 1 d . . . C1 C 0.2949(2) 0.46262(13) 0.95802(7) 0.0386(3) Uani 1 1 d . . . C2 C 0.3780(2) 0.59472(14) 0.96414(7) 0.0407(4) Uani 1 1 d . . . C3 C 0.5664(2) 0.57283(16) 0.94484(8) 0.0458(4) Uani 1 1 d . . . H3A H 0.5812 0.5886 0.9020 0.055 Uiso 1 1 calc R . . H3B H 0.6456 0.6266 0.9673 0.055 Uiso 1 1 calc R . . C4 C 0.5968(2) 0.43686(17) 0.95939(8) 0.0473(4) Uani 1 1 d . . . C5 C 0.1811(2) 0.45125(16) 1.01435(8) 0.0495(4) Uani 1 1 d . . . H5A H 0.1641 0.3633 1.0264 0.059 Uiso 1 1 calc R . . C6 C 0.2857(3) 0.52370(19) 1.06021(8) 0.0604(5) Uani 1 1 d . . . H6A H 0.2092 0.5595 1.0906 0.072 Uiso 1 1 calc R . . H6B H 0.3692 0.4688 1.0800 0.072 Uiso 1 1 calc R . . C7 C 0.2099(2) 0.42857(15) 0.89862(8) 0.0479(4) Uani 1 1 d . . . H7A H 0.2919 0.4443 0.8661 0.058 Uiso 1 1 calc R . . H7B H 0.1093 0.4825 0.8923 0.058 Uiso 1 1 calc R . . C8 C 0.1515(3) 0.29096(18) 0.89605(10) 0.0660(5) Uani 1 1 d . . . H8A H 0.1007 0.2738 0.8573 0.099 Uiso 1 1 calc R . . H8B H 0.0666 0.2756 0.9271 0.099 Uiso 1 1 calc R . . H8C H 0.2506 0.2370 0.9022 0.099 Uiso 1 1 calc R . . C9 C 0.2898(2) 0.70475(15) 0.93355(7) 0.0470(4) Uani 1 1 d . . . H9A H 0.1658 0.7033 0.9425 0.056 Uiso 1 1 calc R . . H9B H 0.3375 0.7830 0.9491 0.056 Uiso 1 1 calc R . . C10 C 0.3230(3) 0.76613(19) 0.74836(9) 0.0639(5) Uani 1 1 d . . . C11 C 0.2671(5) 0.8704(3) 0.70332(12) 0.1176(11) Uani 1 1 d . . . H11A H 0.3215 0.8556 0.6649 0.176 Uiso 1 1 calc R . . H11B H 0.3027 0.9512 0.7185 0.176 Uiso 1 1 calc R . . H11C H 0.1425 0.8690 0.6987 0.176 Uiso 1 1 calc R . . C12 C 0.2694(4) 0.6373(2) 0.72329(13) 0.0999(9) Uani 1 1 d . . . H12A H 0.3253 0.6239 0.6851 0.150 Uiso 1 1 calc R . . H12B H 0.1450 0.6349 0.7181 0.150 Uiso 1 1 calc R . . H12C H 0.3043 0.5725 0.7510 0.150 Uiso 1 1 calc R . . C13 C 0.5225(4) 0.7701(3) 0.75611(14) 0.0973(9) Uani 1 1 d . . . H13A H 0.5776 0.7549 0.7179 0.146 Uiso 1 1 calc R . . H13B H 0.5579 0.7064 0.7843 0.146 Uiso 1 1 calc R . . H13C H 0.5567 0.8515 0.7709 0.146 Uiso 1 1 calc R . . C14 C -0.0226(3) 0.7555(3) 0.82082(15) 0.0941(9) Uani 1 1 d . . . H14A H -0.0370 0.6706 0.8068 0.141 Uiso 1 1 calc R . . H14B H -0.0817 0.8122 0.7940 0.141 Uiso 1 1 calc R . . H14C H -0.0711 0.7632 0.8606 0.141 Uiso 1 1 calc R . . C15 C 0.2462(3) 0.96061(17) 0.84910(12) 0.0824(7) Uani 1 1 d . . . H15A H 0.1897 0.9719 0.8874 0.124 Uiso 1 1 calc R . . H15B H 0.1963 1.0174 0.8201 0.124 Uiso 1 1 calc R . . H15C H 0.3687 0.9777 0.8532 0.124 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 0.0493(3) 0.0415(2) 0.0552(3) 0.0003(2) -0.0080(2) 0.0042(2) O1 0.0373(6) 0.0406(6) 0.0662(8) 0.0064(6) -0.0045(6) 0.0004(5) O2 0.0376(7) 0.0720(8) 0.0933(11) 0.0085(8) -0.0073(7) 0.0070(6) O3 0.0742(8) 0.0577(7) 0.0363(6) -0.0064(6) 0.0017(6) -0.0213(7) O4 0.0433(7) 0.0695(8) 0.0953(12) -0.0177(8) 0.0086(7) 0.0014(6) O5 0.0663(8) 0.0429(6) 0.0422(6) 0.0031(5) 0.0042(5) 0.0109(6) C1 0.0347(7) 0.0357(7) 0.0452(9) 0.0005(6) -0.0024(7) 0.0026(7) C2 0.0470(9) 0.0399(8) 0.0350(8) -0.0025(7) 0.0010(7) -0.0069(7) C3 0.0423(9) 0.0496(9) 0.0453(10) 0.0018(8) 0.0001(7) -0.0118(8) C4 0.0391(9) 0.0554(10) 0.0474(10) 0.0004(8) -0.0060(8) -0.0014(8) C5 0.0447(10) 0.0479(9) 0.0559(11) 0.0020(8) 0.0066(8) -0.0068(8) C6 0.0679(12) 0.0726(11) 0.0407(9) 0.0019(9) 0.0072(9) -0.0187(11) C7 0.0482(9) 0.0440(8) 0.0517(10) -0.0058(8) -0.0078(8) -0.0019(8) C8 0.0688(13) 0.0527(10) 0.0766(14) -0.0163(11) -0.0151(11) -0.0089(10) C9 0.0596(10) 0.0378(7) 0.0436(9) -0.0044(7) 0.0059(8) 0.0006(10) C10 0.0736(14) 0.0672(12) 0.0510(12) 0.0054(10) -0.0069(10) -0.0012(10) C11 0.164(3) 0.123(2) 0.0662(17) 0.0365(16) -0.0189(19) -0.001(3) C12 0.132(2) 0.0908(17) 0.0764(16) -0.0302(14) -0.0032(17) 0.0015(19) C13 0.0755(17) 0.132(2) 0.0841(19) 0.0073(18) 0.0218(13) -0.0056(16) C14 0.0485(12) 0.109(2) 0.125(2) -0.0200(17) -0.0060(14) 0.0033(13) C15 0.113(2) 0.0442(10) 0.0900(16) -0.0041(11) -0.0178(15) 0.0112(13) _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 O5 1.6475(12) . ? Si1 C15 1.862(2) . ? Si1 C14 1.868(2) . ? Si1 C10 1.876(2) . ? O1 C4 1.3488(19) . ? O1 C1 1.4687(18) . ? O2 C4 1.204(2) . ? O3 C6 1.434(2) . ? O3 C2 1.4431(19) . ? O4 C5 1.429(2) . ? O5 C9 1.4216(19) . ? C1 C7 1.512(2) . ? C1 C5 1.527(2) . ? C1 C2 1.546(2) . ? C2 C9 1.510(2) . ? C2 C3 1.522(2) . ? C3 C4 1.497(3) . ? C5 C6 1.505(3) . ? C7 C8 1.528(2) . ? C10 C12 1.531(3) . ? C10 C13 1.538(4) . ? C10 C11 1.551(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 O5 Si1 C15 109.11(9) . . ? O5 Si1 C14 109.25(11) . . ? C15 Si1 C14 110.29(13) . . ? O5 Si1 C10 104.47(8) . . ? C15 Si1 C10 111.87(11) . . ? C14 Si1 C10 111.65(12) . . ? C4 O1 C1 111.38(12) . . ? C6 O3 C2 110.67(13) . . ? C9 O5 Si1 122.46(11) . . ? O1 C1 C7 107.89(12) . . ? O1 C1 C5 106.08(12) . . ? C7 C1 C5 116.58(14) . . ? O1 C1 C2 103.32(12) . . ? C7 C1 C2 118.06(13) . . ? C5 C1 C2 103.58(13) . . ? O3 C2 C9 106.14(13) . . ? O3 C2 C3 108.86(13) . . ? C9 C2 C3 114.58(14) . . ? O3 C2 C1 104.98(12) . . ? C9 C2 C1 118.53(13) . . ? C3 C2 C1 103.13(12) . . ? C4 C3 C2 103.53(13) . . ? O2 C4 O1 120.29(16) . . ? O2 C4 C3 129.44(16) . . ? O1 C4 C3 110.27(14) . . ? O4 C5 C6 108.20(15) . . ? O4 C5 C1 110.24(14) . . ? C6 C5 C1 102.03(14) . . ? O3 C6 C5 106.66(14) . . ? C1 C7 C8 112.74(15) . . ? O5 C9 C2 110.57(13) . . ? C12 C10 C13 109.4(2) . . ? C12 C10 C11 109.2(2) . . ? C13 C10 C11 109.1(2) . . ? C12 C10 Si1 110.44(16) . . ? C13 C10 Si1 109.60(16) . . ? C11 C10 Si1 109.13(17) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 28.01 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.188 _refine_diff_density_min -0.171 _refine_diff_density_rms 0.033 data_ken934 _database_code_CSD 188285 _audit_creation_method SHELXL-97 _chemical_name_systematic ; (1'S,2'R,3'R)-3-[1'-ethyl-1',2'-(isopropylidenedioxy)-3'-hydroxypent-4' -enyl]but-2-en-4-olide ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H24 O5' _chemical_formula_weight 296.35 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' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) 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 8.2731(4) _cell_length_b 11.6606(6) _cell_length_c 17.5669(9) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1694.67(15) _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 Plate _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.31 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.162 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 640 _exptl_absorpt_coefficient_mu 0.085 _exptl_absorpt_correction_type SADABS _exptl_absorpt_correction_T_min 0.5629 _exptl_absorpt_correction_T_max 1.0000 _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 'Bruker SMART CCD Diffractometer' _diffrn_measurement_method 'omega scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11496 _diffrn_reflns_av_R_equivalents 0.0388 _diffrn_reflns_av_sigmaI/netI 0.0416 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.10 _diffrn_reflns_theta_max 27.99 _reflns_number_total 4078 _reflns_number_gt 2709 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART CCD Diffractometer' _computing_cell_refinement 'Bruker SMART CCD Diffractometer' _computing_data_reduction 'Bruker SMART CCD Diffractometer' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Siemens SHLEXTL' _computing_publication_material 'Siemens SHLEXTL' _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^)+(0.0682P)^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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.3(12) _refine_ls_number_reflns 4078 _refine_ls_number_parameters 191 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0735 _refine_ls_R_factor_gt 0.0449 _refine_ls_wR_factor_ref 0.1211 _refine_ls_wR_factor_gt 0.1079 _refine_ls_goodness_of_fit_ref 0.930 _refine_ls_restrained_S_all 0.930 _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 0.2500(2) 0.74678(15) 0.79409(11) 0.0828(5) Uani 1 1 d . . . O2 O 0.33218(17) 0.91963(13) 0.83158(9) 0.0652(4) Uani 1 1 d . . . O3 O 0.76927(17) 0.98104(11) 0.93714(7) 0.0532(4) Uani 1 1 d . . . O4 O 0.89155(18) 1.06714(11) 0.83765(7) 0.0552(4) Uani 1 1 d . . . O5 O 0.70814(18) 0.99424(13) 0.71409(8) 0.0599(4) Uani 1 1 d . . . H5A H 0.7227 1.0638 0.7123 0.090 Uiso 1 1 calc R . . C1 C 0.3583(3) 0.80779(19) 0.81646(12) 0.0569(5) Uani 1 1 d . . . C2 C 0.5269(2) 0.78239(16) 0.83198(11) 0.0481(5) Uani 1 1 d . . . H2A H 0.5750 0.7108 0.8266 0.058 Uiso 1 1 calc R . . C3 C 0.6019(2) 0.87659(15) 0.85490(10) 0.0415(4) Uani 1 1 d . . . C4 C 0.4802(2) 0.97083(17) 0.85781(14) 0.0567(5) Uani 1 1 d . . . H4A H 0.4682 0.9994 0.9094 0.068 Uiso 1 1 calc R . . H4B H 0.5120 1.0338 0.8250 0.068 Uiso 1 1 calc R . . C5 C 0.7751(2) 0.89469(14) 0.87887(10) 0.0409(4) Uani 1 1 d . . . C6 C 0.8482(3) 0.78405(17) 0.91127(10) 0.0494(5) Uani 1 1 d . . . H6A H 0.8407 0.7244 0.8729 0.059 Uiso 1 1 calc R . . H6B H 0.9620 0.7970 0.9214 0.059 Uiso 1 1 calc R . . C7 C 0.7681(3) 0.7414(2) 0.98384(13) 0.0695(7) Uani 1 1 d . . . H7A H 0.8204 0.6724 1.0005 0.104 Uiso 1 1 calc R . . H7B H 0.6560 0.7260 0.9741 0.104 Uiso 1 1 calc R . . H7C H 0.7772 0.7990 1.0227 0.104 Uiso 1 1 calc R . . C8 C 0.8712(3) 1.07559(18) 0.91777(11) 0.0575(5) Uani 1 1 d . . . C9 C 1.0302(3) 1.0645(3) 0.95972(13) 0.0853(8) Uani 1 1 d . . . H9A H 1.0796 0.9924 0.9472 0.128 Uiso 1 1 calc R . . H9B H 1.0111 1.0680 1.0136 0.128 Uiso 1 1 calc R . . H9C H 1.1007 1.1260 0.9450 0.128 Uiso 1 1 calc R . . C10 C 0.7831(4) 1.1855(2) 0.93446(16) 0.0939(9) Uani 1 1 d . . . H10A H 0.6836 1.1873 0.9063 0.141 Uiso 1 1 calc R . . H10B H 0.8492 1.2495 0.9198 0.141 Uiso 1 1 calc R . . H10C H 0.7602 1.1900 0.9880 0.141 Uiso 1 1 calc R . . C11 C 0.8898(2) 0.94899(15) 0.81830(10) 0.0417(4) Uani 1 1 d . . . H11A H 0.9986 0.9187 0.8273 0.050 Uiso 1 1 calc R . . C12 C 0.8550(2) 0.93902(16) 0.73255(10) 0.0454(4) Uani 1 1 d . . . C13 C 0.9975(3) 0.99385(18) 0.68891(11) 0.0564(5) Uani 1 1 d . . . H13A H 1.0097 1.0726 0.7057 0.068 Uiso 1 1 calc R . . H13B H 1.0959 0.9533 0.7021 0.068 Uiso 1 1 calc R . . C14 C 0.9786(4) 0.9929(2) 0.60363(13) 0.0783(7) Uani 1 1 d . . . H14A H 1.0718 1.0275 0.5806 0.117 Uiso 1 1 calc R . . H14B H 0.8836 1.0353 0.5898 0.117 Uiso 1 1 calc R . . H14C H 0.9684 0.9152 0.5862 0.117 Uiso 1 1 calc R . . C15 C 0.8460(3) 0.81421(17) 0.71103(11) 0.0577(6) Uani 1 1 d . . . H15A H 0.9312 0.7674 0.7261 0.069 Uiso 1 1 calc R . . C16 C 0.7290(4) 0.7662(2) 0.67309(14) 0.0895(9) Uani 1 1 d . . . H16C H 0.6415 0.8100 0.6569 0.107 Uiso 1 1 calc R . . H16A H 0.7330 0.6883 0.6621 0.107 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 0.0531(11) 0.0886(12) 0.1067(13) -0.0099(10) -0.0177(9) -0.0184(9) O2 0.0384(8) 0.0671(9) 0.0901(11) -0.0040(8) -0.0078(7) 0.0057(7) O3 0.0517(8) 0.0597(9) 0.0482(7) -0.0113(6) 0.0082(6) -0.0071(6) O4 0.0725(10) 0.0457(7) 0.0475(7) -0.0041(6) 0.0006(7) -0.0121(7) O5 0.0554(9) 0.0657(9) 0.0584(8) 0.0041(7) -0.0143(7) 0.0021(7) C1 0.0458(12) 0.0624(13) 0.0626(12) -0.0005(10) -0.0012(10) -0.0066(10) C2 0.0450(12) 0.0429(10) 0.0565(11) 0.0004(9) 0.0031(9) 0.0019(8) C3 0.0384(10) 0.0419(9) 0.0443(9) 0.0034(7) 0.0051(8) 0.0047(8) C4 0.0409(11) 0.0484(11) 0.0806(15) -0.0031(9) -0.0019(10) 0.0060(9) C5 0.0389(9) 0.0422(10) 0.0414(9) -0.0034(7) 0.0013(8) 0.0025(8) C6 0.0423(11) 0.0569(11) 0.0489(10) 0.0074(9) 0.0020(9) 0.0058(9) C7 0.0726(16) 0.0775(15) 0.0585(12) 0.0235(11) 0.0080(12) 0.0135(13) C8 0.0699(15) 0.0536(11) 0.0489(11) -0.0094(9) 0.0052(10) -0.0131(11) C9 0.0812(19) 0.118(2) 0.0565(13) -0.0140(14) -0.0090(13) -0.0369(17) C10 0.131(3) 0.0598(15) 0.0909(18) -0.0237(13) 0.0197(19) -0.0062(17) C11 0.0365(10) 0.0440(9) 0.0446(9) -0.0003(7) -0.0024(8) 0.0008(8) C12 0.0465(11) 0.0458(10) 0.0439(9) 0.0005(8) -0.0029(8) 0.0005(9) C13 0.0625(13) 0.0579(12) 0.0487(11) 0.0044(9) 0.0051(10) -0.0065(11) C14 0.114(2) 0.0687(14) 0.0527(13) 0.0076(11) 0.0088(13) -0.0101(15) C15 0.0750(15) 0.0498(11) 0.0482(10) -0.0052(9) 0.0158(11) -0.0069(11) C16 0.115(3) 0.0789(16) 0.0741(16) -0.0294(13) 0.0200(17) -0.0357(17) _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 1.209(3) . ? O2 C1 1.348(3) . ? O2 C4 1.438(3) . ? O3 C8 1.429(3) . ? O3 C5 1.437(2) . ? O4 C11 1.419(2) . ? O4 C8 1.421(2) . ? O5 C12 1.413(2) . ? C1 C2 1.452(3) . ? C2 C3 1.324(3) . ? C3 C4 1.491(3) . ? C3 C5 1.508(3) . ? C5 C6 1.534(2) . ? C5 C11 1.560(3) . ? C6 C7 1.521(3) . ? C8 C10 1.504(4) . ? C8 C9 1.513(4) . ? C11 C12 1.538(2) . ? C12 C15 1.506(3) . ? C12 C13 1.545(3) . ? C13 C14 1.506(3) . ? C15 C16 1.301(4) . ? 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 O2 C4 109.17(16) . . ? C8 O3 C5 110.55(13) . . ? C11 O4 C8 107.67(14) . . ? O1 C1 O2 121.0(2) . . ? O1 C1 C2 130.7(2) . . ? O2 C1 C2 108.30(18) . . ? C3 C2 C1 109.76(17) . . ? C2 C3 C4 107.78(17) . . ? C2 C3 C5 130.24(17) . . ? C4 C3 C5 121.92(16) . . ? O2 C4 C3 104.96(15) . . ? O3 C5 C3 105.36(14) . . ? O3 C5 C6 109.77(14) . . ? C3 C5 C6 111.12(15) . . ? O3 C5 C11 102.83(13) . . ? C3 C5 C11 116.37(15) . . ? C6 C5 C11 110.77(15) . . ? C7 C6 C5 114.45(17) . . ? O4 C8 O3 104.61(14) . . ? O4 C8 C10 108.04(19) . . ? O3 C8 C10 108.96(19) . . ? O4 C8 C9 111.94(18) . . ? O3 C8 C9 109.33(19) . . ? C10 C8 C9 113.5(2) . . ? O4 C11 C12 108.06(14) . . ? O4 C11 C5 103.70(14) . . ? C12 C11 C5 121.58(15) . . ? O5 C12 C15 109.88(18) . . ? O5 C12 C11 110.56(16) . . ? C15 C12 C11 109.17(15) . . ? O5 C12 C13 110.71(15) . . ? C15 C12 C13 108.26(16) . . ? C11 C12 C13 108.19(16) . . ? C14 C13 C12 114.29(19) . . ? C16 C15 C12 125.5(2) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 27.99 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.251 _refine_diff_density_min -0.125 _refine_diff_density_rms 0.033 data_ken136 _database_code_CSD 188701 _audit_creation_method SHELXL-97 _chemical_name_systematic ; (1S,5S,8R)-3-1-ethyl-5-(tert-butyldimethylsiloxy)methyl-8-hydroxy-2, 6-dioxabicyclo[3.3.0]octane ; _chemical_name_common ; (1S,5S,8R)-3-1-ethyl-5-(tert-butyldimethylsiloxy)methyl-8-hydroxy-2, 6-dioxabicyclo[3.3.0]octane ; _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H28 O5 Si' _chemical_formula_weight 316.46 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' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Si' 'Si' 0.0817 0.0704 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 10.179(2) _cell_length_b 7.4299(15) _cell_length_c 13.032(3) _cell_angle_alpha 90.00 _cell_angle_beta 105.87(3) _cell_angle_gamma 90.00 _cell_volume 948.0(3) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.55 _exptl_crystal_size_mid 0.50 _exptl_crystal_size_min 0.35 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.109 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 344 _exptl_absorpt_coefficient_mu 0.140 _exptl_absorpt_correction_type none _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 'Bruker SMART 1K CCD area detector' _diffrn_measurement_method 'phi and omega scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 2756 _diffrn_reflns_av_R_equivalents 0.0277 _diffrn_reflns_av_sigmaI/netI 0.0480 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.26 _diffrn_reflns_theta_max 25.66 _reflns_number_total 2698 _reflns_number_gt 2400 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART for Windows NT, Bruker AXS Inc. (1997)' _computing_cell_refinement 'SAINT-PlUS for Windows NT, Bruker AXS Inc. Ver. 5.0' _computing_data_reduction 'SAINT-Plus for Windows NT, Bruker AXS Inc. Ver. 5.0' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XP-Bruker Interactive Molecular Graphics, Ver. 5.1 (1998)' _computing_publication_material 'SHELXTL-Bruker AXS Inc. (1998)' _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^)+(0.2000P)^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 0.21(5) _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 0.7(4) _refine_ls_number_reflns 2698 _refine_ls_number_parameters 217 _refine_ls_number_restraints 10 _refine_ls_R_factor_all 0.1221 _refine_ls_R_factor_gt 0.1172 _refine_ls_wR_factor_ref 0.3126 _refine_ls_wR_factor_gt 0.3036 _refine_ls_goodness_of_fit_ref 1.330 _refine_ls_restrained_S_all 1.364 _refine_ls_shift/su_max 0.015 _refine_ls_shift/su_mean 0.001 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 0.3173(3) 0.9693(4) 0.71875(19) 0.0919(7) Uani 0.50 1 d P . . Si2 Si 0.3405(2) 0.8995(4) 0.68500(18) 0.0851(6) Uani 0.50 1 d PD . . O1 O 0.4759(3) 0.9965(5) 0.7619(2) 0.1035(9) Uani 1 1 d . . . O2 O 0.6095(4) 1.1884(5) 0.9517(2) 0.1042(9) Uani 1 1 d . . . O3 O 0.7517(8) 1.4689(9) 0.7957(5) 0.111(2) Uani 0.50 1 d P . . O3' O 0.7407(10) 1.5044(11) 0.7746(6) 0.107(2) Uani 0.50 1 d P . . O4 O 0.8847(3) 1.1996(5) 0.9052(2) 0.1044(10) Uani 1 1 d . . . O5 O 1.0131(8) 1.0977(14) 1.0636(9) 0.172(4) Uani 0.50 1 d P . . O5' O 1.0218(14) 1.1256(18) 1.0668(8) 0.140(4) Uani 0.50 1 d P . . C3 C 0.1160(5) 1.0043(12) 0.5265(6) 0.172(3) Uani 1 1 d D . . H3A H 0.0891 1.0369 0.4524 0.258 Uiso 1 1 calc R . . H3B H 0.0667 1.0766 0.5646 0.258 Uiso 1 1 calc R . . H3C H 0.0958 0.8795 0.5338 0.258 Uiso 1 1 calc R . . C4 C 0.2685(6) 1.0358(9) 0.5721(5) 0.179(3) Uani 1 1 d D . . C1 C 0.2994(10) 1.2373(8) 0.5863(7) 0.215 Uiso 1 1 d D . . C2 C 0.3437(8) 0.9726(15) 0.4855(5) 0.215 Uiso 1 1 d D . . C5 C 0.2294(17) 1.163(2) 0.772(2) 0.262(8) Uani 0.50 1 d P . . H5A H 0.2445 1.1490 0.8478 0.392 Uiso 0.50 1 calc PR . . H5B H 0.1331 1.1602 0.7378 0.392 Uiso 0.50 1 calc PR . . H5C H 0.2667 1.2755 0.7577 0.392 Uiso 0.50 1 calc PR . . C6 C 0.3960(19) 0.769(3) 0.5791(13) 0.246(7) Uani 0.50 1 d P . . H6A H 0.3424 0.6620 0.5547 0.296 Uiso 0.50 1 calc PR . . H6B H 0.4931 0.7431 0.5979 0.296 Uiso 0.50 1 calc PR . . C7 C 0.2496(9) 0.7572(15) 0.7543(7) 0.162(3) Uani 1 1 d . . . H7A H 0.2989 0.6920 0.8176 0.195 Uiso 1 1 calc R . . H7B H 0.1557 0.7231 0.7204 0.195 Uiso 1 1 calc R . . C8 C 0.5731(5) 0.9136(7) 0.8492(3) 0.0939(12) Uani 1 1 d . . . H8A H 0.6174 0.8143 0.8236 0.113 Uiso 1 1 calc R . . H8B H 0.5273 0.8665 0.8997 0.113 Uiso 1 1 calc R . . C9 C 0.6803(4) 1.0543(6) 0.9043(3) 0.0869(11) Uani 1 1 d . . . C10 C 0.6347(7) 1.3663(9) 0.9148(5) 0.126(2) Uani 1 1 d . . . H10A H 0.7080 1.4255 0.9674 0.151 Uiso 1 1 calc R . . H10B H 0.5532 1.4401 0.9024 0.151 Uiso 1 1 calc R . . C11 C 0.6735(5) 1.3395(7) 0.8131(4) 0.0964(13) Uani 1 1 d . . . C12 C 0.7501(4) 1.1591(7) 0.8360(3) 0.0875(11) Uani 1 1 d . . . C13 C 0.7683(6) 1.0768(11) 0.7294(4) 0.1216(18) Uani 1 1 d . . . H13A H 0.6797 1.0379 0.6856 0.146 Uiso 1 1 calc R . . H13B H 0.8009 1.1705 0.6907 0.146 Uiso 1 1 calc R . . C14 C 0.8681(11) 0.9162(15) 0.7457(9) 0.170(3) Uani 1 1 d . . . H14A H 0.8732 0.8728 0.6775 0.204 Uiso 1 1 calc R . . H14B H 0.8359 0.8216 0.7828 0.204 Uiso 1 1 calc R . . H14C H 0.9570 0.9542 0.7868 0.204 Uiso 1 1 calc R . . C15 C 0.9095(6) 1.0935(8) 0.9920(5) 0.1168(17) Uani 1 1 d . . . C16 C 0.7947(5) 0.9696(8) 0.9916(4) 0.1051(14) Uani 1 1 d . . . H16A H 0.7735 0.9695 1.0598 0.126 Uiso 1 1 calc R . . H16B H 0.8139 0.8476 0.9735 0.126 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 0.0867(13) 0.1026(16) 0.0827(11) -0.0080(11) 0.0169(10) -0.0169(12) Si2 0.0692(11) 0.0947(14) 0.0852(12) -0.0072(11) 0.0104(9) -0.0054(11) O1 0.0808(17) 0.102(2) 0.1070(18) 0.0157(16) -0.0099(14) -0.0016(15) O2 0.1062(19) 0.102(2) 0.1015(15) -0.0029(16) 0.0237(14) 0.0182(17) O3 0.103(4) 0.087(3) 0.102(3) 0.054(3) -0.043(3) -0.020(3) O3' 0.110(5) 0.083(4) 0.097(4) 0.047(3) -0.025(3) -0.002(3) O4 0.0774(16) 0.102(2) 0.1092(17) 0.0041(17) -0.0154(14) -0.0045(15) O5 0.105(4) 0.107(6) 0.215(7) -0.019(5) -0.109(5) 0.020(4) O5' 0.164(10) 0.112(7) 0.116(5) 0.024(5) -0.009(6) 0.000(6) C3 0.115(4) 0.163(7) 0.189(6) 0.009(5) -0.042(4) -0.012(5) C4 0.138(5) 0.197(7) 0.151(4) 0.070(5) -0.047(4) -0.064(5) C5 0.224(11) 0.144(9) 0.50(2) -0.173(12) 0.238(12) -0.082(9) C6 0.228(13) 0.324(17) 0.235(10) -0.193(11) 0.145(10) -0.070(14) C7 0.138(5) 0.170(7) 0.158(5) 0.030(5) 0.007(5) -0.045(5) C8 0.082(2) 0.086(2) 0.101(2) 0.0101(19) 0.0043(19) -0.003(2) C9 0.081(2) 0.087(2) 0.0803(18) -0.0005(16) 0.0006(17) 0.0070(18) C10 0.125(4) 0.099(4) 0.143(4) -0.003(3) 0.020(3) 0.025(3) C11 0.084(2) 0.093(3) 0.097(2) 0.016(2) -0.002(2) -0.001(2) C12 0.0659(19) 0.099(3) 0.086(2) 0.0012(18) 0.0017(16) -0.0032(18) C13 0.099(3) 0.163(5) 0.107(3) -0.029(3) 0.036(2) -0.028(3) C14 0.180(6) 0.122(6) 0.223(8) -0.022(6) 0.080(6) 0.000(5) C15 0.096(3) 0.089(3) 0.132(3) -0.011(3) -0.025(3) 0.008(2) C16 0.099(3) 0.097(3) 0.098(2) 0.010(2) -0.006(2) 0.018(2)> _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 Si2 0.758(3) . ? Si1 O1 1.571(4) . ? Si1 C7 1.830(10) . ? Si1 C4 1.904(6) . ? Si1 C5 1.921(15) . ? Si2 O1 1.633(4) . ? Si2 C4 1.771(6) . ? Si2 C7 1.802(9) . ? Si2 C6 1.894(13) . ? O1 C8 1.428(5) . ? O2 C10 1.454(9) . ? O2 C9 1.462(6) . ? O3 C11 1.307(9) . ? O3' C11 1.553(10) . ? O4 C15 1.344(7) . ? O4 C12 1.451(5) . ? O5 C15 1.203(9) . ? O5' C15 1.306(12) . ? C3 C4 1.521(6) . ? C4 C1 1.530(7) . ? C4 C2 1.598(8) . ? C2 C6 1.92(3) . ? C8 C9 1.540(6) . ? C9 C12 1.499(7) . ? C9 C16 1.523(6) . ? C10 C11 1.495(9) . ? C11 C12 1.538(7) . ? C12 C13 1.575(7) . ? C13 C14 1.544(13) . ? C15 C16 1.487(9) . ? 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 Si2 Si1 O1 81.0(3) . . ? Si2 Si1 C7 75.9(5) . . ? O1 Si1 C7 116.2(4) . . ? Si2 Si1 C4 68.4(3) . . ? O1 Si1 C4 106.6(3) . . ? C7 Si1 C4 117.7(3) . . ? Si2 Si1 C5 166.3(9) . . ? O1 Si1 C5 108.0(6) . . ? C7 Si1 C5 107.9(7) . . ? C4 Si1 C5 98.7(9) . . ? Si1 Si2 O1 71.7(3) . . ? Si1 Si2 C4 88.1(4) . . ? O1 Si2 C4 110.2(3) . . ? Si1 Si2 C7 80.0(5) . . ? O1 Si2 C7 114.5(3) . . ? C4 Si2 C7 126.8(4) . . ? Si1 Si2 C6 167.0(9) . . ? O1 Si2 C6 107.6(6) . . ? C4 Si2 C6 79.9(8) . . ? C7 Si2 C6 111.2(9) . . ? C8 O1 Si1 130.6(3) . . ? C8 O1 Si2 125.7(3) . . ? Si1 O1 Si2 27.28(13) . . ? C10 O2 C9 109.1(4) . . ? C15 O4 C12 109.2(4) . . ? C3 C4 C1 110.6(6) . . ? C3 C4 C2 108.3(5) . . ? C1 C4 C2 104.5(6) . . ? C3 C4 Si2 112.5(5) . . ? C1 C4 Si2 115.7(5) . . ? C2 C4 Si2 104.5(5) . . ? C3 C4 Si1 108.1(4) . . ? C1 C4 Si1 98.3(5) . . ? C2 C4 Si1 126.1(5) . . ? Si2 C4 Si1 23.45(13) . . ? C4 C2 C6 83.5(6) . . ? Si2 C6 C2 88.6(10) . . ? Si2 C7 Si1 24.08(16) . . ? O1 C8 C9 109.1(4) . . ? O2 C9 C12 105.4(4) . . ? O2 C9 C16 109.3(3) . . ? C12 C9 C16 105.6(4) . . ? O2 C9 C8 106.9(4) . . ? C12 C9 C8 117.8(3) . . ? C16 C9 C8 111.5(4) . . ? O2 C10 C11 106.6(5) . . ? O3 C11 C10 112.1(6) . . ? O3 C11 C12 112.0(5) . . ? C10 C11 C12 100.8(4) . . ? O3 C11 O3' 11.5(4) . . ? C10 C11 O3' 115.3(5) . . ? C12 C11 O3' 120.4(5) . . ? O4 C12 C9 105.0(3) . . ? O4 C12 C11 106.4(4) . . ? C9 C12 C11 105.7(4) . . ? O4 C12 C13 108.0(4) . . ? C9 C12 C13 120.8(5) . . ? C11 C12 C13 110.1(4) . . ? C14 C13 C12 114.3(6) . . ? O5 C15 O5' 9.1(9) . . ? O5 C15 O4 124.0(8) . . ? O5' C15 O4 116.5(7) . . ? O5 C15 C16 122.7(8) . . ? O5' C15 C16 130.0(7) . . ? O4 C15 C16 113.2(4) . . ? C15 C16 C9 100.7(4) . . ? _diffrn_measured_fraction_theta_max 0.846 _diffrn_reflns_theta_full 25.66 _diffrn_measured_fraction_theta_full 0.846 _refine_diff_density_max 0.619 _refine_diff_density_min -0.490 _refine_diff_density_rms 0.083