data_publication_text _publ_requested_journal J.Am.Chem.Soc. _publ_contact_author_name 'Professor Shahriar Mobashery' _publ_contact_author_address ;University of Notre Dame Department of Chemistry and Biochemistry 251 Nieuwland Science Hall Notre Dame, IN 46556-5670 USA ; _publ_contact_author_email mobashery@nd.edu _publ_contact_author_phone 1(574)6312933 _publ_contact_author_fax 1(574)6316652 loop_ _publ_author_name _publ_author_address 'Hesek, Dusan' ;University of Notre Dame Department of Chemistry and Biochemistry 251 Nieuwland Science Hall Notre Dame, IN 46556-5670 USA ; 'Lee, Mijoon' ;University of Notre Dame Department of Chemistry and Biochemistry 251 Nieuwland Science Hall Notre Dame, IN 46556-5670 USA ; 'Zhang, Welie' ;University of Notre Dame Department of Chemistry and Biochemistry 251 Nieuwland Science Hall Notre Dame, IN 46556-5670 USA ; 'Noll, Bruce C.' ;University of Notre Dame Department of Chemistry and Biochemistry 251 Nieuwland Science Hall Notre Dame, IN 46556-5670 USA ; ' Mobashery, Shahriar' ;University of Notre Dame Department of Chemistry and Biochemistry 251 Nieuwland Science Hall Notre Dame, IN 46556-5670 USA ; data_compound_4a # local ID: data_dh46_1_0m _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common 4-O-benzyl-6-O-tert-butyldimethylsilyl-D-(-)-glucal _chemical_melting_point ? _chemical_formula_moiety 'C19 H30 O4 Si' _chemical_formula_sum 'C19 H30 O4 Si' _chemical_formula_weight 350.52 _chemical_absolute_configuration ad 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' 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' _symmetry_int_tables_number 19 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x+1/2, -y, z+1/2' _cell_length_a 6.6344(2) _cell_length_b 10.9383(2) _cell_length_c 27.1190(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1968.00(8) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 9897 _cell_measurement_theta_min 3.26 _cell_measurement_theta_max 65.69 _exptl_crystal_description plate _exptl_crystal_colour clear _exptl_crystal_size_max 0.44 _exptl_crystal_size_mid 0.152 _exptl_crystal_size_min 0.097 _exptl_crystal_density_meas . _exptl_crystal_density_diffrn 1.183 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 760 _exptl_absorpt_coefficient_mu 1.202 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.84 _exptl_absorpt_correction_T_max 0.91 _exptl_absorpt_process_details 'Sheldrick, G. M. (2008) SADABS. University of G\"ottingen, Germany.' _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_probe x-ray _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54178 _diffrn_source 'fine-focus sealed tube' _diffrn_source_type 'Siemens KFFCU2K-90' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART Apex CCD area detector' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean 8.33 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 25085 _diffrn_reflns_av_R_equivalents 0.0271 _diffrn_reflns_av_sigmaI/netI 0.0198 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -30 _diffrn_reflns_limit_l_max 31 _diffrn_reflns_theta_min 3.26 _diffrn_reflns_theta_max 66.22 _reflns_number_total 3313 _reflns_number_gt 3238 _reflns_threshold_expression >2sigma(I) _publ_section_references ; Bruker-Nonius AXS. (2007). APEX2 and SAINT. Bruker-Nonius AXS, Madison, Wisconsin, USA. CCDC. (2005). enCIFer. The Cambridge Crystallographic Data Centre, Cambridge, UK. Sheldrick, G. M. (2007). SADABS. University of G\"ottingen, Germany. Sheldrick, G.M. (2008). Acta Cryst. A64, 112-122. ; _computing_data_collection 'APEX2 (Bruker, 2007)' _computing_cell_refinement 'APEX2/SAINT (Bruker, 2007)' _computing_data_reduction 'SAINT/XPREP (Bruker, 2007; Sheldrick, 2008)' _computing_structure_solution 'XS (Sheldrick, 2008)' _computing_structure_refinement 'XL (Sheldrick, 2008)' _computing_molecular_graphics 'XP (Sheldrick, 2008)' _computing_publication_material 'XCIF (Sheldrick, 2008)/enCIFer (CCDC, 2005)' _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^)+(0.0393P)^2^+0.4125P] 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 0.03(2) _refine_ls_number_reflns 3313 _refine_ls_number_parameters 223 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0273 _refine_ls_R_factor_gt 0.0265 _refine_ls_wR_factor_ref 0.0686 _refine_ls_wR_factor_gt 0.0683 _refine_ls_goodness_of_fit_ref 1.055 _refine_ls_restrained_S_all 1.055 _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 0.08771(6) 0.47928(3) 0.829122(14) 0.02113(11) Uani 1 1 d . . . O1 O 0.46389(18) 0.36434(9) 0.95921(4) 0.0284(3) Uani 1 1 d . . . O2 O 0.26111(15) 0.47269(9) 0.87324(3) 0.0222(2) Uani 1 1 d . . . O3 O 0.44740(17) 0.69928(9) 0.94316(4) 0.0257(2) Uani 1 1 d . . . O4 O 0.85404(17) 0.65416(10) 0.97439(4) 0.0296(3) Uani 1 1 d . . . H4O H 0.8933 0.6958 0.9976 0.044 Uiso 1 1 calc R . . C1 C 0.6390(3) 0.35836(14) 0.98579(5) 0.0282(4) Uani 1 1 d . . . H1 H 0.6894 0.2812 0.9932 0.034 Uiso 1 1 calc R . . C2 C 0.7416(2) 0.45376(14) 1.00167(5) 0.0263(3) Uani 1 1 d . . . H2 H 0.8543 0.4404 1.0213 0.032 Uiso 1 1 calc R . . C3 C 0.6846(2) 0.58300(14) 0.98946(5) 0.0238(3) Uani 1 1 d . . . H3 H 0.6225 0.6210 1.0184 0.029 Uiso 1 1 calc R . . C4 C 0.5328(2) 0.58056(13) 0.94749(5) 0.0203(3) Uani 1 1 d . . . H4 H 0.6022 0.5596 0.9167 0.024 Uiso 1 1 calc R . . C5 C 0.3733(2) 0.48401(13) 0.95846(5) 0.0234(3) Uani 1 1 d . . . H5 H 0.3202 0.5003 0.9915 0.028 Uiso 1 1 calc R . . C6 C 0.1964(2) 0.47975(15) 0.92345(5) 0.0252(3) Uani 1 1 d . . . H6A H 0.1135 0.4092 0.9311 0.030 Uiso 1 1 calc R . . H6B H 0.1146 0.5524 0.9279 0.030 Uiso 1 1 calc R . . C7 C -0.0480(2) 0.62887(13) 0.83118(6) 0.0302(3) Uani 1 1 d . . . H7A H -0.0845 0.6472 0.8646 0.045 Uiso 1 1 calc R . . H7C H -0.1674 0.6241 0.8113 0.045 Uiso 1 1 calc R . . H7B H 0.0384 0.6921 0.8187 0.045 Uiso 1 1 calc R . . C8 C 0.2279(2) 0.46096(14) 0.76940(5) 0.0258(3) Uani 1 1 d . . . C9 C 0.3924(3) 0.55860(17) 0.76512(6) 0.0403(4) Uani 1 1 d . . . H9A H 0.4862 0.5496 0.7918 0.060 Uiso 1 1 calc R . . H9B H 0.3321 0.6383 0.7665 0.060 Uiso 1 1 calc R . . H9C H 0.4621 0.5490 0.7343 0.060 Uiso 1 1 calc R . . C10 C 0.0792(3) 0.47470(17) 0.72615(6) 0.0381(4) Uani 1 1 d . . . H10A H 0.0210 0.5550 0.7268 0.057 Uiso 1 1 calc R . . H10B H -0.0256 0.4146 0.7291 0.057 Uiso 1 1 calc R . . H10C H 0.1496 0.4630 0.6956 0.057 Uiso 1 1 calc R . . C11 C 0.3258(3) 0.33428(16) 0.76653(6) 0.0347(4) Uani 1 1 d . . . H11A H 0.3970 0.3264 0.7359 0.052 Uiso 1 1 calc R . . H11B H 0.2232 0.2725 0.7685 0.052 Uiso 1 1 calc R . . H11C H 0.4183 0.3245 0.7934 0.052 Uiso 1 1 calc R . . C12 C -0.1032(3) 0.35658(14) 0.83896(6) 0.0314(4) Uani 1 1 d . . . H12A H -0.0363 0.2791 0.8418 0.047 Uiso 1 1 calc R . . H12B H -0.1943 0.3546 0.8115 0.047 Uiso 1 1 calc R . . H12C H -0.1772 0.3729 0.8687 0.047 Uiso 1 1 calc R . . C13 C 0.4152(3) 0.74328(14) 0.89409(6) 0.0380(4) Uani 1 1 d . . . H13A H 0.2775 0.7267 0.8841 0.046 Uiso 1 1 calc R . . H13B H 0.5046 0.7010 0.8715 0.046 Uiso 1 1 calc R . . C14 C 0.4545(3) 0.87853(14) 0.89177(5) 0.0267(4) Uani 1 1 d . . . C15 C 0.6395(3) 0.92596(16) 0.90655(6) 0.0316(4) Uani 1 1 d . . . H15B H 0.7382 0.8741 0.9190 0.038 Uiso 1 1 calc R . . C16 C 0.6770(3) 1.04967(17) 0.90284(6) 0.0392(5) Uani 1 1 d . . . H16B H 0.8009 1.0809 0.9127 0.047 Uiso 1 1 calc R . . C17 C 0.5300(3) 1.12743(16) 0.88444(6) 0.0401(5) Uani 1 1 d . . . H17B H 0.5554 1.2108 0.8819 0.048 Uiso 1 1 calc R . . C18 C 0.3460(3) 1.08094(15) 0.86989(6) 0.0354(4) Uani 1 1 d . . . H18B H 0.2473 1.1330 0.8575 0.042 Uiso 1 1 calc R . . C19 C 0.3085(3) 0.95662(14) 0.87369(6) 0.0291(4) Uani 1 1 d . . . H19B H 0.1842 0.9256 0.8640 0.035 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 0.0209(2) 0.01953(18) 0.02299(19) 0.00209(15) -0.00314(15) -0.00268(16) O1 0.0383(7) 0.0191(5) 0.0279(5) 0.0031(4) -0.0078(5) -0.0012(5) O2 0.0230(6) 0.0237(5) 0.0197(5) 0.0006(4) -0.0006(4) -0.0014(4) O3 0.0360(6) 0.0180(5) 0.0230(5) -0.0014(4) -0.0030(4) 0.0052(4) O4 0.0302(7) 0.0307(6) 0.0278(5) -0.0062(5) -0.0020(5) -0.0066(5) C1 0.0380(10) 0.0237(8) 0.0231(7) 0.0042(6) -0.0039(7) 0.0046(6) C2 0.0298(8) 0.0287(8) 0.0204(7) 0.0012(6) -0.0043(6) 0.0061(7) C3 0.0262(8) 0.0255(8) 0.0197(7) -0.0030(6) 0.0002(6) 0.0000(6) C4 0.0266(8) 0.0158(7) 0.0184(7) -0.0025(5) 0.0011(6) 0.0018(6) C5 0.0284(8) 0.0236(7) 0.0183(6) 0.0013(5) 0.0024(6) 0.0009(6) C6 0.0236(8) 0.0304(7) 0.0216(7) 0.0015(6) 0.0028(6) -0.0028(7) C7 0.0284(9) 0.0259(8) 0.0364(8) 0.0019(7) -0.0062(7) 0.0028(6) C8 0.0307(9) 0.0256(8) 0.0211(7) 0.0010(6) -0.0022(6) -0.0044(6) C9 0.0449(11) 0.0449(10) 0.0310(8) -0.0020(7) 0.0107(8) -0.0174(8) C10 0.0473(11) 0.0417(9) 0.0253(8) 0.0010(7) -0.0088(8) 0.0025(9) C11 0.0371(10) 0.0383(9) 0.0286(8) -0.0031(7) -0.0005(7) 0.0055(8) C12 0.0262(9) 0.0284(8) 0.0394(9) 0.0038(7) -0.0027(7) -0.0080(7) C13 0.0628(13) 0.0226(8) 0.0287(8) -0.0005(6) -0.0183(9) 0.0036(8) C14 0.0396(10) 0.0224(8) 0.0180(7) -0.0024(6) -0.0011(6) 0.0015(7) C15 0.0331(10) 0.0383(9) 0.0234(7) -0.0057(7) 0.0014(7) 0.0018(7) C16 0.0431(11) 0.0503(11) 0.0242(8) -0.0062(7) 0.0092(7) -0.0201(9) C17 0.0721(15) 0.0247(9) 0.0236(8) 0.0009(6) 0.0114(8) -0.0151(9) C18 0.0556(12) 0.0247(8) 0.0258(7) 0.0055(7) 0.0019(8) 0.0075(8) C19 0.0366(9) 0.0274(8) 0.0232(7) 0.0010(6) -0.0042(7) -0.0008(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 Si1 O2 1.6613(10) . ? Si1 C12 1.8645(16) . ? Si1 C7 1.8683(15) . ? Si1 C8 1.8785(16) . ? O1 C1 1.3690(19) . ? O1 C5 1.4406(18) . ? O2 C6 1.4298(17) . ? O3 C4 1.4217(17) . ? O3 C13 1.4312(19) . ? O4 C3 1.4272(19) . ? O4 H4O 0.8200 . ? C1 C2 1.318(2) . ? C1 H1 0.9300 . ? C2 C3 1.500(2) . ? C2 H2 0.9300 . ? C3 C4 1.520(2) . ? C3 H3 0.9800 . ? C4 C5 1.525(2) . ? C4 H4 0.9800 . ? C5 C6 1.510(2) . ? C5 H5 0.9800 . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 H7A 0.9600 . ? C7 H7C 0.9600 . ? C7 H7B 0.9600 . ? C8 C9 1.531(2) . ? C8 C11 1.532(2) . ? C8 C10 1.540(2) . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C13 C14 1.504(2) . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C14 C19 1.381(2) . ? C14 C15 1.391(2) . ? C15 C16 1.380(3) . ? C15 H15B 0.9300 . ? C16 C17 1.387(3) . ? C16 H16B 0.9300 . ? C17 C18 1.380(3) . ? C17 H17B 0.9300 . ? C18 C19 1.386(2) . ? C18 H18B 0.9300 . ? C19 H19B 0.9300 . ? 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 O2 Si1 C12 109.63(6) . . ? O2 Si1 C7 110.50(6) . . ? C12 Si1 C7 107.40(8) . . ? O2 Si1 C8 105.87(6) . . ? C12 Si1 C8 112.52(7) . . ? C7 Si1 C8 110.96(7) . . ? C1 O1 C5 113.90(11) . . ? C6 O2 Si1 118.39(9) . . ? C4 O3 C13 116.32(11) . . ? C3 O4 H4O 109.5 . . ? C2 C1 O1 124.91(14) . . ? C2 C1 H1 117.5 . . ? O1 C1 H1 117.5 . . ? C1 C2 C3 122.94(14) . . ? C1 C2 H2 118.5 . . ? C3 C2 H2 118.5 . . ? O4 C3 C2 112.24(13) . . ? O4 C3 C4 108.49(11) . . ? C2 C3 C4 108.41(12) . . ? O4 C3 H3 109.2 . . ? C2 C3 H3 109.2 . . ? C4 C3 H3 109.2 . . ? O3 C4 C3 108.06(11) . . ? O3 C4 C5 111.85(12) . . ? C3 C4 C5 109.02(11) . . ? O3 C4 H4 109.3 . . ? C3 C4 H4 109.3 . . ? C5 C4 H4 109.3 . . ? O1 C5 C6 107.76(12) . . ? O1 C5 C4 110.02(12) . . ? C6 C5 C4 115.98(12) . . ? O1 C5 H5 107.6 . . ? C6 C5 H5 107.6 . . ? C4 C5 H5 107.6 . . ? O2 C6 C5 111.54(12) . . ? O2 C6 H6A 109.3 . . ? C5 C6 H6A 109.3 . . ? O2 C6 H6B 109.3 . . ? C5 C6 H6B 109.3 . . ? H6A C6 H6B 108.0 . . ? Si1 C7 H7A 109.5 . . ? Si1 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? Si1 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? H7C C7 H7B 109.5 . . ? C9 C8 C11 108.96(14) . . ? C9 C8 C10 109.32(13) . . ? C11 C8 C10 108.71(13) . . ? C9 C8 Si1 110.11(10) . . ? C11 C8 Si1 110.49(10) . . ? C10 C8 Si1 109.21(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 C11 H11A 109.5 . . ? C8 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C8 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? Si1 C12 H12A 109.5 . . ? Si1 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? Si1 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? O3 C13 C14 110.11(12) . . ? O3 C13 H13A 109.6 . . ? C14 C13 H13A 109.6 . . ? O3 C13 H13B 109.6 . . ? C14 C13 H13B 109.6 . . ? H13A C13 H13B 108.2 . . ? C19 C14 C15 119.35(15) . . ? C19 C14 C13 120.10(16) . . ? C15 C14 C13 120.52(16) . . ? C16 C15 C14 120.26(17) . . ? C16 C15 H15B 119.9 . . ? C14 C15 H15B 119.9 . . ? C15 C16 C17 120.06(18) . . ? C15 C16 H16B 120.0 . . ? C17 C16 H16B 120.0 . . ? C18 C17 C16 119.92(16) . . ? C18 C17 H17B 120.0 . . ? C16 C17 H17B 120.0 . . ? C17 C18 C19 119.94(17) . . ? C17 C18 H18B 120.0 . . ? C19 C18 H18B 120.0 . . ? C14 C19 C18 120.47(17) . . ? C14 C19 H19B 119.8 . . ? C18 C19 H19B 119.8 . . ? _diffrn_measured_fraction_theta_max 0.972 _diffrn_reflns_theta_full 66.22 _diffrn_measured_fraction_theta_full 0.972 _refine_diff_density_max 0.266 _refine_diff_density_min -0.137 _refine_diff_density_rms 0.036 _chemical_compound_source synthesized