Supplementary Material (ESI) for Organic & Biomolecular Chemistry This journal is (c) The Royal Society of Chemistry 2006 data_global _journal_coden_Cambridge 177 loop_ _publ_author_name 'Richard Hsung' 'Changhong Ko' _publ_contact_author_name 'Richard Hsung' _publ_contact_author_address ; Pharmaceutical Science Division University of Wisconsin Department of Chemistry 777 Highland Avenue Madison WI 53705 UNITED STATES OF AMERICA ; _publ_contact_author_email RHSUNG@WISC.EDU _publ_requested_journal 'Organic & Biomolecular Chemistry' _publ_section_title ; An Unusual Stereoselectivity in the Anomeric Substitution with Carbamates Promoted by HNTf2. ; # Attachment 'anomeric_substitution_X-ray.cif' data_05263 _database_code_depnum_ccdc_archive 'CCDC 625894' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 05263 _chemical_melting_point ? _chemical_formula_moiety '2(C22 H35 N O4 Si)' _chemical_formula_sum 'C44 H70 N2 O8 Si2' _chemical_formula_weight 811.20 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' 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)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 18.967(3) _cell_length_b 12.7861(18) _cell_length_c 19.491(3) _cell_angle_alpha 90.00 _cell_angle_beta 96.878(2) _cell_angle_gamma 90.00 _cell_volume 4693.0(11) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 2726 _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.148 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1760 _exptl_absorpt_coefficient_mu 0.125 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9634 _exptl_absorpt_correction_T_max 0.9876 _exptl_absorpt_process_details 'SADABS, R. Blessing, 1995' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'normal-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART Platform CCD' _diffrn_measurement_method 'area detector, omega scans per phi' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 45086 _diffrn_reflns_av_R_equivalents 0.0984 _diffrn_reflns_av_sigmaI/netI 0.0732 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 1.91 _diffrn_reflns_theta_max 25.11 _reflns_number_total 8336 _reflns_number_gt 4809 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART, Bruker' _computing_cell_refinement 'SAINT, Bruker' _computing_data_reduction 'SAINT, Bruker' _computing_structure_solution SIR97 _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL, Bruker' _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^)+(0.1158P)^2^+4.5575P] 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 riding _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 8336 _refine_ls_number_parameters 515 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1338 _refine_ls_R_factor_gt 0.0697 _refine_ls_wR_factor_ref 0.2237 _refine_ls_wR_factor_gt 0.1745 _refine_ls_goodness_of_fit_ref 1.022 _refine_ls_restrained_S_all 1.022 _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 0.11974(14) 0.7018(2) 0.05859(13) 0.0278(6) Uani 1 1 d . . . C2 C 0.1662(2) 0.6438(4) 0.0195(2) 0.0366(10) Uani 1 1 d . . . H2A H 0.2137 0.6382 0.0466 0.044 Uiso 1 1 calc R . . H2B H 0.1716 0.6818 -0.0238 0.044 Uiso 1 1 calc R . . C3 C 0.1377(3) 0.5357(4) 0.0023(2) 0.0478(12) Uani 1 1 d . . . H3A H 0.1705 0.4975 -0.0247 0.057 Uiso 1 1 calc R . . H3B H 0.0909 0.5405 -0.0260 0.057 Uiso 1 1 calc R . . C4 C 0.1305(3) 0.4770(3) 0.0700(2) 0.0429(12) Uani 1 1 d . . . H4A H 0.1082 0.4080 0.0595 0.051 Uiso 1 1 calc R . . H4B H 0.1780 0.4655 0.0958 0.051 Uiso 1 1 calc R . . C5 C 0.0852(2) 0.5410(3) 0.1133(2) 0.0303(9) Uani 1 1 d . . . H5A H 0.0861 0.5080 0.1593 0.036 Uiso 1 1 calc R . . H5B H 0.0354 0.5404 0.0910 0.036 Uiso 1 1 calc R . . C6 C 0.1100(2) 0.6542(3) 0.12257(19) 0.0241(8) Uani 1 1 d . . . C7 C 0.0532(2) 0.7220(3) 0.15225(18) 0.0231(8) Uani 1 1 d . . . H7 H 0.0732 0.7934 0.1627 0.028 Uiso 1 1 calc R . . C8 C -0.0138(2) 0.7317(3) 0.1025(2) 0.0344(10) Uani 1 1 d . . . H8 H -0.0106 0.7668 0.0600 0.041 Uiso 1 1 calc R . . C9 C -0.0756(2) 0.6956(4) 0.1135(2) 0.0500(13) Uani 1 1 d . . . H9A H -0.0809 0.6600 0.1554 0.060 Uiso 1 1 calc R . . H9B H -0.1155 0.7047 0.0796 0.060 Uiso 1 1 calc R . . O10 O 0.03983(14) 0.6737(2) 0.21486(12) 0.0256(6) Uani 1 1 d . . . Si11 Si 0.03182(6) 0.72883(8) 0.29017(5) 0.0241(3) Uani 1 1 d . . . C12 C -0.0567(2) 0.7910(4) 0.2899(3) 0.0488(13) Uani 1 1 d . . . H12A H -0.0938 0.7382 0.2793 0.073 Uiso 1 1 calc R . . H12B H -0.0623 0.8462 0.2548 0.073 Uiso 1 1 calc R . . H12C H -0.0606 0.8213 0.3355 0.073 Uiso 1 1 calc R . . C13 C 0.1032(3) 0.8277(4) 0.3113(2) 0.0432(12) Uani 1 1 d . . . H13A H 0.1494 0.7925 0.3185 0.065 Uiso 1 1 calc R . . H13B H 0.0950 0.8651 0.3536 0.065 Uiso 1 1 calc R . . H13C H 0.1027 0.8776 0.2731 0.065 Uiso 1 1 calc R . . C14 C 0.1136(3) 0.5665(4) 0.3540(3) 0.0566(15) Uani 1 1 d . . . H14A H 0.1171 0.5059 0.3850 0.085 Uiso 1 1 calc R . . H14B H 0.1496 0.6183 0.3710 0.085 Uiso 1 1 calc R . . H14C H 0.1215 0.5441 0.3074 0.085 Uiso 1 1 calc R . . C15 C 0.0271(3) 0.6514(4) 0.4242(2) 0.0463(12) Uani 1 1 d . . . H15A H 0.0323 0.5918 0.4561 0.069 Uiso 1 1 calc R . . H15B H -0.0210 0.6800 0.4226 0.069 Uiso 1 1 calc R . . H15C H 0.0618 0.7054 0.4403 0.069 Uiso 1 1 calc R . . C16 C -0.0164(3) 0.5323(4) 0.3269(2) 0.0466(12) Uani 1 1 d . . . H16A H -0.0122 0.4728 0.3589 0.070 Uiso 1 1 calc R . . H16B H -0.0090 0.5083 0.2806 0.070 Uiso 1 1 calc R . . H16C H -0.0639 0.5631 0.3256 0.070 Uiso 1 1 calc R . . C17 C 0.0399(2) 0.6150(3) 0.3517(2) 0.0289(9) Uani 1 1 d . . . N18 N 0.17615(16) 0.6540(2) 0.17062(16) 0.0250(7) Uani 1 1 d . . . H18 H 0.1898 0.5926 0.1878 0.030 Uiso 1 1 calc R . . C19 C 0.2186(2) 0.7351(3) 0.1919(2) 0.0259(9) Uani 1 1 d . . . O20 O 0.26712(14) 0.7294(2) 0.23881(14) 0.0336(7) Uani 1 1 d . . . O21 O 0.20291(13) 0.8237(2) 0.15574(13) 0.0278(6) Uani 1 1 d . . . C22 C 0.2512(2) 0.9084(3) 0.1738(2) 0.0327(10) Uani 1 1 d . . . H22A H 0.2998 0.8880 0.1654 0.039 Uiso 1 1 calc R . . H22B H 0.2521 0.9252 0.2235 0.039 Uiso 1 1 calc R . . C23 C 0.2277(2) 1.0019(3) 0.13116(19) 0.0255(9) Uani 1 1 d . . . C24 C 0.2629(2) 1.0958(3) 0.1464(2) 0.0350(10) Uani 1 1 d . . . H24 H 0.3000 1.0987 0.1837 0.042 Uiso 1 1 calc R . . C25 C 0.2450(3) 1.1848(3) 0.1083(2) 0.0426(12) Uani 1 1 d . . . H25 H 0.2696 1.2484 0.1197 0.051 Uiso 1 1 calc R . . C26 C 0.1916(2) 1.1818(3) 0.0538(2) 0.0387(11) Uani 1 1 d . . . H26 H 0.1794 1.2428 0.0272 0.046 Uiso 1 1 calc R . . C27 C 0.1560(2) 1.0888(3) 0.0384(2) 0.0336(10) Uani 1 1 d . . . H27 H 0.1188 1.0865 0.0011 0.040 Uiso 1 1 calc R . . C28 C 0.1734(2) 0.9990(3) 0.07632(19) 0.0281(9) Uani 1 1 d . . . H28 H 0.1485 0.9357 0.0650 0.034 Uiso 1 1 calc R . . O29 O 0.35910(13) 0.4922(2) 0.42825(13) 0.0269(6) Uani 1 1 d . . . C30 C 0.3002(2) 0.5288(3) 0.4619(2) 0.0347(10) Uani 1 1 d . . . H30A H 0.2951 0.4845 0.5027 0.042 Uiso 1 1 calc R . . H30B H 0.2558 0.5233 0.4297 0.042 Uiso 1 1 calc R . . C31 C 0.3115(3) 0.6404(4) 0.4845(2) 0.0452(12) Uani 1 1 d . . . H31A H 0.3536 0.6451 0.5197 0.054 Uiso 1 1 calc R . . H31B H 0.2697 0.6656 0.5056 0.054 Uiso 1 1 calc R . . C32 C 0.3227(3) 0.7089(4) 0.4226(2) 0.0456(12) Uani 1 1 d . . . H32A H 0.2781 0.7124 0.3907 0.055 Uiso 1 1 calc R . . H32B H 0.3351 0.7808 0.4387 0.055 Uiso 1 1 calc R . . C33 C 0.3818(2) 0.6651(3) 0.3846(2) 0.0324(10) Uani 1 1 d . . . H33A H 0.4280 0.6746 0.4136 0.039 Uiso 1 1 calc R . . H33B H 0.3835 0.7045 0.3412 0.039 Uiso 1 1 calc R . . C34 C 0.3707(2) 0.5493(3) 0.36804(18) 0.0251(9) Uani 1 1 d . . . C35 C 0.4360(2) 0.4964(3) 0.34230(19) 0.0263(9) Uani 1 1 d . . . H35 H 0.4240 0.4218 0.3308 0.032 Uiso 1 1 calc R . . C36 C 0.4989(2) 0.4990(4) 0.3968(2) 0.0405(11) Uani 1 1 d . . . H36 H 0.4969 0.4572 0.4368 0.049 Uiso 1 1 calc R . . C37 C 0.5562(3) 0.5544(5) 0.3934(3) 0.0653(17) Uani 1 1 d . . . H37A H 0.5602 0.5972 0.3542 0.078 Uiso 1 1 calc R . . H37B H 0.5940 0.5520 0.4301 0.078 Uiso 1 1 calc R . . O38 O 0.44986(14) 0.5484(2) 0.28149(13) 0.0286(6) Uani 1 1 d . . . Si39 Si 0.46717(6) 0.49214(9) 0.20915(6) 0.0282(3) Uani 1 1 d . . . C40 C 0.5563(3) 0.4300(4) 0.2210(3) 0.0581(14) Uani 1 1 d . . . H40A H 0.5929 0.4843 0.2285 0.087 Uiso 1 1 calc R . . H40B H 0.5633 0.3897 0.1796 0.087 Uiso 1 1 calc R . . H40C H 0.5598 0.3833 0.2611 0.087 Uiso 1 1 calc R . . C41 C 0.3996(3) 0.3901(4) 0.1819(2) 0.0486(13) Uani 1 1 d . . . H41A H 0.3536 0.4235 0.1678 0.073 Uiso 1 1 calc R . . H41B H 0.3953 0.3425 0.2205 0.073 Uiso 1 1 calc R . . H41C H 0.4142 0.3506 0.1429 0.073 Uiso 1 1 calc R . . C42 C 0.5201(4) 0.6845(4) 0.1717(3) 0.0707(18) Uani 1 1 d . . . H42A H 0.5172 0.7437 0.1395 0.106 Uiso 1 1 calc R . . H42B H 0.5676 0.6533 0.1747 0.106 Uiso 1 1 calc R . . H42C H 0.5112 0.7091 0.2175 0.106 Uiso 1 1 calc R . . C43 C 0.3905(3) 0.6512(5) 0.1361(3) 0.076(2) Uani 1 1 d . . . H43A H 0.3889 0.7067 0.1013 0.115 Uiso 1 1 calc R . . H43B H 0.3800 0.6809 0.1802 0.115 Uiso 1 1 calc R . . H43C H 0.3552 0.5976 0.1209 0.115 Uiso 1 1 calc R . . C44 C 0.4819(3) 0.5613(4) 0.0757(2) 0.0511(13) Uani 1 1 d . . . H44A H 0.4789 0.6188 0.0422 0.077 Uiso 1 1 calc R . . H44B H 0.4481 0.5064 0.0591 0.077 Uiso 1 1 calc R . . H44C H 0.5301 0.5325 0.0812 0.077 Uiso 1 1 calc R . . C45 C 0.4641(2) 0.6022(3) 0.1455(2) 0.0382(11) Uani 1 1 d . . . N46 N 0.30930(16) 0.5435(2) 0.31416(16) 0.0256(7) Uani 1 1 d . . . H46 H 0.2952 0.6035 0.2951 0.031 Uiso 1 1 calc R . . C47 C 0.2718(2) 0.4593(3) 0.29004(19) 0.0242(8) Uani 1 1 d . . . O48 O 0.22367(14) 0.4618(2) 0.24234(14) 0.0317(7) Uani 1 1 d . . . O49 O 0.29114(14) 0.3708(2) 0.32464(14) 0.0289(6) Uani 1 1 d . . . C50 C 0.2454(2) 0.2817(3) 0.3081(2) 0.0371(11) Uani 1 1 d . . . H50A H 0.2476 0.2600 0.2596 0.045 Uiso 1 1 calc R . . H50B H 0.1957 0.3003 0.3133 0.045 Uiso 1 1 calc R . . C51 C 0.2699(2) 0.1945(3) 0.3561(2) 0.0267(9) Uani 1 1 d . . . C52 C 0.2528(2) 0.0923(3) 0.3366(2) 0.0360(10) Uani 1 1 d . . . H52 H 0.2262 0.0791 0.2930 0.043 Uiso 1 1 calc R . . C53 C 0.2741(2) 0.0099(3) 0.3797(2) 0.0413(11) Uani 1 1 d . . . H53 H 0.2625 -0.0597 0.3657 0.050 Uiso 1 1 calc R . . C54 C 0.3120(2) 0.0286(3) 0.4432(2) 0.0414(11) Uani 1 1 d . . . H54 H 0.3263 -0.0284 0.4730 0.050 Uiso 1 1 calc R . . C55 C 0.3296(3) 0.1295(4) 0.4640(2) 0.0437(12) Uani 1 1 d . . . H55 H 0.3557 0.1418 0.5080 0.052 Uiso 1 1 calc R . . C56 C 0.3089(2) 0.2132(3) 0.4205(2) 0.0355(10) Uani 1 1 d . . . H56 H 0.3213 0.2827 0.4344 0.043 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 0.0316(15) 0.0299(15) 0.0223(14) 0.0056(12) 0.0052(11) 0.0041(12) C2 0.036(2) 0.051(3) 0.025(2) 0.002(2) 0.0130(19) 0.002(2) C3 0.057(3) 0.050(3) 0.040(3) -0.014(2) 0.020(2) -0.003(2) C4 0.053(3) 0.030(2) 0.048(3) -0.007(2) 0.012(2) 0.001(2) C5 0.038(2) 0.024(2) 0.028(2) 0.0013(17) 0.0029(18) -0.0012(18) C6 0.025(2) 0.027(2) 0.021(2) 0.0037(16) 0.0022(16) 0.0047(16) C7 0.026(2) 0.023(2) 0.0191(19) 0.0024(16) -0.0006(15) 0.0022(16) C8 0.033(2) 0.042(3) 0.026(2) 0.0044(19) -0.0027(18) 0.010(2) C9 0.036(3) 0.077(4) 0.034(3) -0.004(2) -0.007(2) 0.002(3) O10 0.0311(15) 0.0273(15) 0.0183(13) 0.0007(11) 0.0025(11) 0.0004(12) Si11 0.0261(6) 0.0239(6) 0.0219(6) -0.0018(4) 0.0019(4) 0.0005(5) C12 0.045(3) 0.047(3) 0.054(3) -0.003(2) 0.004(2) 0.023(2) C13 0.053(3) 0.047(3) 0.029(2) -0.005(2) 0.000(2) -0.018(2) C14 0.045(3) 0.075(4) 0.052(3) 0.035(3) 0.014(2) 0.025(3) C15 0.059(3) 0.056(3) 0.024(2) -0.001(2) 0.006(2) -0.012(3) C16 0.070(3) 0.032(3) 0.041(3) 0.000(2) 0.018(2) -0.015(2) C17 0.025(2) 0.039(2) 0.023(2) 0.0034(18) 0.0049(17) 0.0014(18) N18 0.0241(17) 0.0224(17) 0.0278(18) 0.0075(14) 0.0005(14) 0.0047(14) C19 0.026(2) 0.023(2) 0.029(2) 0.0072(17) 0.0045(17) 0.0083(17) O20 0.0289(16) 0.0347(17) 0.0346(16) 0.0113(13) -0.0072(13) 0.0016(13) O21 0.0277(15) 0.0213(14) 0.0321(15) 0.0090(12) -0.0056(12) -0.0034(11) C22 0.035(2) 0.027(2) 0.034(2) 0.0053(18) -0.0082(18) -0.0068(18) C23 0.024(2) 0.028(2) 0.025(2) 0.0027(17) 0.0063(16) 0.0012(17) C24 0.041(3) 0.032(2) 0.031(2) 0.0057(19) 0.0001(19) -0.012(2) C25 0.062(3) 0.029(2) 0.037(3) 0.002(2) 0.002(2) -0.015(2) C26 0.054(3) 0.027(2) 0.037(3) 0.008(2) 0.010(2) 0.005(2) C27 0.037(2) 0.036(2) 0.028(2) 0.0065(19) 0.0043(18) 0.010(2) C28 0.027(2) 0.030(2) 0.027(2) -0.0011(17) 0.0031(17) 0.0017(18) O29 0.0293(15) 0.0304(15) 0.0213(14) 0.0080(11) 0.0035(11) 0.0077(12) C30 0.033(2) 0.044(3) 0.028(2) 0.0045(19) 0.0086(18) 0.010(2) C31 0.056(3) 0.046(3) 0.034(3) -0.004(2) 0.005(2) 0.014(2) C32 0.056(3) 0.034(3) 0.046(3) -0.008(2) 0.002(2) 0.009(2) C33 0.036(2) 0.027(2) 0.032(2) 0.0028(18) -0.0081(18) -0.0018(18) C34 0.026(2) 0.030(2) 0.0183(19) 0.0058(16) -0.0025(15) 0.0023(17) C35 0.025(2) 0.031(2) 0.022(2) 0.0041(17) 0.0007(16) 0.0018(17) C36 0.030(2) 0.064(3) 0.026(2) 0.009(2) -0.0034(18) 0.011(2) C37 0.028(3) 0.116(5) 0.049(3) 0.012(3) -0.011(2) -0.012(3) O38 0.0284(15) 0.0366(16) 0.0210(14) 0.0030(12) 0.0039(11) -0.0020(12) Si39 0.0266(6) 0.0300(6) 0.0280(6) -0.0008(5) 0.0040(5) 0.0000(5) C40 0.048(3) 0.058(4) 0.068(4) 0.002(3) 0.010(3) 0.019(3) C41 0.057(3) 0.051(3) 0.039(3) -0.015(2) 0.012(2) -0.016(3) C42 0.119(5) 0.042(3) 0.058(4) -0.007(3) 0.038(4) -0.023(3) C43 0.087(4) 0.094(5) 0.052(3) 0.032(3) 0.023(3) 0.048(4) C44 0.063(3) 0.062(3) 0.031(3) -0.005(2) 0.018(2) -0.004(3) C45 0.050(3) 0.039(3) 0.028(2) 0.004(2) 0.013(2) 0.004(2) N46 0.0265(17) 0.0234(17) 0.0256(18) 0.0061(14) -0.0025(14) 0.0033(14) C47 0.025(2) 0.027(2) 0.022(2) 0.0080(17) 0.0053(16) 0.0052(17) O48 0.0307(15) 0.0309(16) 0.0307(16) 0.0067(12) -0.0085(13) 0.0022(12) O49 0.0298(15) 0.0219(14) 0.0329(16) 0.0094(12) -0.0053(12) -0.0013(12) C50 0.040(3) 0.027(2) 0.041(3) 0.0060(19) -0.010(2) -0.004(2) C51 0.025(2) 0.025(2) 0.031(2) 0.0039(17) 0.0060(17) 0.0018(17) C52 0.042(3) 0.031(2) 0.035(2) 0.0036(19) 0.001(2) -0.006(2) C53 0.051(3) 0.028(2) 0.046(3) 0.004(2) 0.010(2) -0.006(2) C54 0.045(3) 0.031(3) 0.049(3) 0.017(2) 0.005(2) 0.005(2) C55 0.058(3) 0.036(3) 0.036(3) 0.010(2) 0.000(2) 0.004(2) C56 0.046(3) 0.030(2) 0.028(2) 0.0023(18) -0.0037(19) 0.005(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 O1 C6 1.420(4) . ? O1 C2 1.438(5) . ? C2 C3 1.507(6) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.538(6) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 C5 1.515(6) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 C6 1.525(5) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 N18 1.472(5) . ? C6 C7 1.548(5) . ? C7 O10 1.417(4) . ? C7 C8 1.509(5) . ? C7 H7 1.0000 . ? C8 C9 1.303(6) . ? C8 H8 0.9500 . ? C9 H9A 0.9500 . ? C9 H9B 0.9500 . ? O10 Si11 1.652(3) . ? Si11 C12 1.856(4) . ? Si11 C13 1.862(4) . ? Si11 C17 1.880(4) . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C14 C17 1.525(6) . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C15 C17 1.535(6) . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C16 C17 1.539(6) . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? N18 C19 1.347(5) . ? N18 H18 0.8800 . ? C19 O20 1.219(4) . ? C19 O21 1.348(4) . ? O21 C22 1.435(4) . ? C22 C23 1.494(5) . ? C22 H22A 0.9900 . ? C22 H22B 0.9900 . ? C23 C24 1.388(6) . ? C23 C28 1.393(5) . ? C24 C25 1.378(6) . ? C24 H24 0.9500 . ? C25 C26 1.379(6) . ? C25 H25 0.9500 . ? C26 C27 1.383(6) . ? C26 H26 0.9500 . ? C27 C28 1.384(6) . ? C27 H27 0.9500 . ? C28 H28 0.9500 . ? O29 C34 1.422(4) . ? O29 C30 1.441(5) . ? C30 C31 1.500(6) . ? C30 H30A 0.9900 . ? C30 H30B 0.9900 . ? C31 C32 1.525(6) . ? C31 H31A 0.9900 . ? C31 H31B 0.9900 . ? C32 C33 1.522(6) . ? C32 H32A 0.9900 . ? C32 H32B 0.9900 . ? C33 C34 1.524(6) . ? C33 H33A 0.9900 . ? C33 H33B 0.9900 . ? C34 N46 1.473(5) . ? C34 C35 1.547(5) . ? C35 O38 1.411(4) . ? C35 C36 1.500(5) . ? C35 H35 1.0000 . ? C36 C37 1.306(7) . ? C36 H36 0.9500 . ? C37 H37A 0.9500 . ? C37 H37B 0.9500 . ? O38 Si39 1.650(3) . ? Si39 C40 1.857(5) . ? Si39 C41 1.862(5) . ? Si39 C45 1.872(4) . ? C40 H40A 0.9800 . ? C40 H40B 0.9800 . ? C40 H40C 0.9800 . ? C41 H41A 0.9800 . ? C41 H41B 0.9800 . ? C41 H41C 0.9800 . ? C42 C45 1.538(7) . ? C42 H42A 0.9800 . ? C42 H42B 0.9800 . ? C42 H42C 0.9800 . ? C43 C45 1.521(7) . ? C43 H43A 0.9800 . ? C43 H43B 0.9800 . ? C43 H43C 0.9800 . ? C44 C45 1.533(6) . ? C44 H44A 0.9800 . ? C44 H44B 0.9800 . ? C44 H44C 0.9800 . ? N46 C47 1.343(5) . ? N46 H46 0.8800 . ? C47 O48 1.223(4) . ? C47 O49 1.346(4) . ? O49 C50 1.444(5) . ? C50 C51 1.494(5) . ? C50 H50A 0.9900 . ? C50 H50B 0.9900 . ? C51 C52 1.387(6) . ? C51 C56 1.400(6) . ? C52 C53 1.378(6) . ? C52 H52 0.9500 . ? C53 C54 1.376(6) . ? C53 H53 0.9500 . ? C54 C55 1.381(6) . ? C54 H54 0.9500 . ? C55 C56 1.393(6) . ? C55 H55 0.9500 . ? C56 H56 0.9500 . ? 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 C6 O1 C2 113.3(3) . . ? O1 C2 C3 111.4(3) . . ? O1 C2 H2A 109.3 . . ? C3 C2 H2A 109.3 . . ? O1 C2 H2B 109.3 . . ? C3 C2 H2B 109.3 . . ? H2A C2 H2B 108.0 . . ? C2 C3 C4 108.8(4) . . ? C2 C3 H3A 109.9 . . ? C4 C3 H3A 109.9 . . ? C2 C3 H3B 109.9 . . ? C4 C3 H3B 109.9 . . ? H3A C3 H3B 108.3 . . ? C5 C4 C3 109.2(4) . . ? C5 C4 H4A 109.8 . . ? C3 C4 H4A 109.8 . . ? C5 C4 H4B 109.8 . . ? C3 C4 H4B 109.8 . . ? H4A C4 H4B 108.3 . . ? C4 C5 C6 113.0(3) . . ? C4 C5 H5A 109.0 . . ? C6 C5 H5A 109.0 . . ? C4 C5 H5B 109.0 . . ? C6 C5 H5B 109.0 . . ? H5A C5 H5B 107.8 . . ? O1 C6 N18 111.7(3) . . ? O1 C6 C5 111.9(3) . . ? N18 C6 C5 107.6(3) . . ? O1 C6 C7 104.9(3) . . ? N18 C6 C7 109.9(3) . . ? C5 C6 C7 110.9(3) . . ? O10 C7 C8 111.5(3) . . ? O10 C7 C6 106.4(3) . . ? C8 C7 C6 112.1(3) . . ? O10 C7 H7 108.9 . . ? C8 C7 H7 108.9 . . ? C6 C7 H7 108.9 . . ? C9 C8 C7 124.8(4) . . ? C9 C8 H8 117.6 . . ? C7 C8 H8 117.6 . . ? C8 C9 H9A 120.0 . . ? C8 C9 H9B 120.0 . . ? H9A C9 H9B 120.0 . . ? C7 O10 Si11 128.7(2) . . ? O10 Si11 C12 111.06(19) . . ? O10 Si11 C13 110.17(18) . . ? C12 Si11 C13 110.1(2) . . ? O10 Si11 C17 103.14(16) . . ? C12 Si11 C17 109.7(2) . . ? C13 Si11 C17 112.5(2) . . ? Si11 C12 H12A 109.5 . . ? Si11 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? Si11 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? Si11 C13 H13A 109.5 . . ? Si11 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? Si11 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C17 C14 H14A 109.5 . . ? C17 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C17 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C17 C15 H15A 109.5 . . ? C17 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C17 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C17 C16 H16A 109.5 . . ? C17 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C17 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C14 C17 C15 110.0(4) . . ? C14 C17 C16 109.2(4) . . ? C15 C17 C16 108.4(3) . . ? C14 C17 Si11 109.8(3) . . ? C15 C17 Si11 110.1(3) . . ? C16 C17 Si11 109.4(3) . . ? C19 N18 C6 128.8(3) . . ? C19 N18 H18 115.6 . . ? C6 N18 H18 115.6 . . ? O20 C19 N18 123.7(3) . . ? O20 C19 O21 122.8(4) . . ? N18 C19 O21 113.5(3) . . ? C19 O21 C22 114.3(3) . . ? O21 C22 C23 109.2(3) . . ? O21 C22 H22A 109.8 . . ? C23 C22 H22A 109.8 . . ? O21 C22 H22B 109.8 . . ? C23 C22 H22B 109.8 . . ? H22A C22 H22B 108.3 . . ? C24 C23 C28 118.7(4) . . ? C24 C23 C22 118.0(3) . . ? C28 C23 C22 123.4(4) . . ? C25 C24 C23 121.2(4) . . ? C25 C24 H24 119.4 . . ? C23 C24 H24 119.4 . . ? C24 C25 C26 120.2(4) . . ? C24 C25 H25 119.9 . . ? C26 C25 H25 119.9 . . ? C25 C26 C27 119.1(4) . . ? C25 C26 H26 120.4 . . ? C27 C26 H26 120.4 . . ? C26 C27 C28 121.2(4) . . ? C26 C27 H27 119.4 . . ? C28 C27 H27 119.4 . . ? C27 C28 C23 119.7(4) . . ? C27 C28 H28 120.1 . . ? C23 C28 H28 120.1 . . ? C34 O29 C30 114.4(3) . . ? O29 C30 C31 110.5(4) . . ? O29 C30 H30A 109.5 . . ? C31 C30 H30A 109.5 . . ? O29 C30 H30B 109.5 . . ? C31 C30 H30B 109.5 . . ? H30A C30 H30B 108.1 . . ? C30 C31 C32 110.1(4) . . ? C30 C31 H31A 109.6 . . ? C32 C31 H31A 109.6 . . ? C30 C31 H31B 109.6 . . ? C32 C31 H31B 109.6 . . ? H31A C31 H31B 108.2 . . ? C33 C32 C31 110.7(4) . . ? C33 C32 H32A 109.5 . . ? C31 C32 H32A 109.5 . . ? C33 C32 H32B 109.5 . . ? C31 C32 H32B 109.5 . . ? H32A C32 H32B 108.1 . . ? C32 C33 C34 111.7(4) . . ? C32 C33 H33A 109.3 . . ? C34 C33 H33A 109.3 . . ? C32 C33 H33B 109.3 . . ? C34 C33 H33B 109.3 . . ? H33A C33 H33B 107.9 . . ? O29 C34 N46 112.0(3) . . ? O29 C34 C33 110.8(3) . . ? N46 C34 C33 106.2(3) . . ? O29 C34 C35 104.6(3) . . ? N46 C34 C35 110.0(3) . . ? C33 C34 C35 113.4(3) . . ? O38 C35 C36 111.9(3) . . ? O38 C35 C34 107.7(3) . . ? C36 C35 C34 111.1(3) . . ? O38 C35 H35 108.7 . . ? C36 C35 H35 108.7 . . ? C34 C35 H35 108.7 . . ? C37 C36 C35 124.9(4) . . ? C37 C36 H36 117.6 . . ? C35 C36 H36 117.6 . . ? C36 C37 H37A 120.0 . . ? C36 C37 H37B 120.0 . . ? H37A C37 H37B 120.0 . . ? C35 O38 Si39 126.1(3) . . ? O38 Si39 C40 110.6(2) . . ? O38 Si39 C41 110.40(18) . . ? C40 Si39 C41 108.8(3) . . ? O38 Si39 C45 104.16(17) . . ? C40 Si39 C45 111.1(2) . . ? C41 Si39 C45 111.9(2) . . ? Si39 C40 H40A 109.5 . . ? Si39 C40 H40B 109.5 . . ? H40A C40 H40B 109.5 . . ? Si39 C40 H40C 109.5 . . ? H40A C40 H40C 109.5 . . ? H40B C40 H40C 109.5 . . ? Si39 C41 H41A 109.5 . . ? Si39 C41 H41B 109.5 . . ? H41A C41 H41B 109.5 . . ? Si39 C41 H41C 109.5 . . ? H41A C41 H41C 109.5 . . ? H41B C41 H41C 109.5 . . ? C45 C42 H42A 109.5 . . ? C45 C42 H42B 109.5 . . ? H42A C42 H42B 109.5 . . ? C45 C42 H42C 109.5 . . ? H42A C42 H42C 109.5 . . ? H42B C42 H42C 109.5 . . ? C45 C43 H43A 109.5 . . ? C45 C43 H43B 109.5 . . ? H43A C43 H43B 109.5 . . ? C45 C43 H43C 109.5 . . ? H43A C43 H43C 109.5 . . ? H43B C43 H43C 109.5 . . ? C45 C44 H44A 109.5 . . ? C45 C44 H44B 109.5 . . ? H44A C44 H44B 109.5 . . ? C45 C44 H44C 109.5 . . ? H44A C44 H44C 109.5 . . ? H44B C44 H44C 109.5 . . ? C43 C45 C44 109.3(4) . . ? C43 C45 C42 110.2(5) . . ? C44 C45 C42 108.1(4) . . ? C43 C45 Si39 110.1(3) . . ? C44 C45 Si39 109.8(3) . . ? C42 C45 Si39 109.3(3) . . ? C47 N46 C34 129.1(3) . . ? C47 N46 H46 115.5 . . ? C34 N46 H46 115.5 . . ? O48 C47 N46 124.1(3) . . ? O48 C47 O49 122.4(4) . . ? N46 C47 O49 113.4(3) . . ? C47 O49 C50 115.5(3) . . ? O49 C50 C51 108.4(3) . . ? O49 C50 H50A 110.0 . . ? C51 C50 H50A 110.0 . . ? O49 C50 H50B 110.0 . . ? C51 C50 H50B 110.0 . . ? H50A C50 H50B 108.4 . . ? C52 C51 C56 119.2(4) . . ? C52 C51 C50 119.1(4) . . ? C56 C51 C50 121.7(4) . . ? C53 C52 C51 120.7(4) . . ? C53 C52 H52 119.6 . . ? C51 C52 H52 119.6 . . ? C54 C53 C52 120.0(4) . . ? C54 C53 H53 120.0 . . ? C52 C53 H53 120.0 . . ? C53 C54 C55 120.5(4) . . ? C53 C54 H54 119.7 . . ? C55 C54 H54 119.7 . . ? C54 C55 C56 119.9(4) . . ? C54 C55 H55 120.0 . . ? C56 C55 H55 120.0 . . ? C55 C56 C51 119.6(4) . . ? C55 C56 H56 120.2 . . ? C51 C56 H56 120.2 . . ? 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 C6 O1 C2 C3 60.3(4) . . . . ? O1 C2 C3 C4 -59.7(5) . . . . ? C2 C3 C4 C5 54.9(5) . . . . ? C3 C4 C5 C6 -50.9(5) . . . . ? C2 O1 C6 N18 66.6(4) . . . . ? C2 O1 C6 C5 -54.1(4) . . . . ? C2 O1 C6 C7 -174.4(3) . . . . ? C4 C5 C6 O1 50.3(4) . . . . ? C4 C5 C6 N18 -72.7(4) . . . . ? C4 C5 C6 C7 167.1(3) . . . . ? O1 C6 C7 O10 177.4(3) . . . . ? N18 C6 C7 O10 -62.4(4) . . . . ? C5 C6 C7 O10 56.4(4) . . . . ? O1 C6 C7 C8 55.3(4) . . . . ? N18 C6 C7 C8 175.5(3) . . . . ? C5 C6 C7 C8 -65.7(4) . . . . ? O10 C7 C8 C9 -3.5(6) . . . . ? C6 C7 C8 C9 115.6(5) . . . . ? C8 C7 O10 Si11 -101.7(4) . . . . ? C6 C7 O10 Si11 135.8(3) . . . . ? C7 O10 Si11 C12 77.5(3) . . . . ? C7 O10 Si11 C13 -44.8(3) . . . . ? C7 O10 Si11 C17 -165.1(3) . . . . ? O10 Si11 C17 C14 63.7(3) . . . . ? C12 Si11 C17 C14 -177.9(3) . . . . ? C13 Si11 C17 C14 -55.0(4) . . . . ? O10 Si11 C17 C15 -175.1(3) . . . . ? C12 Si11 C17 C15 -56.7(3) . . . . ? C13 Si11 C17 C15 66.2(3) . . . . ? O10 Si11 C17 C16 -56.1(3) . . . . ? C12 Si11 C17 C16 62.3(3) . . . . ? C13 Si11 C17 C16 -174.8(3) . . . . ? O1 C6 N18 C19 53.9(5) . . . . ? C5 C6 N18 C19 177.1(4) . . . . ? C7 C6 N18 C19 -62.1(5) . . . . ? C6 N18 C19 O20 169.9(4) . . . . ? C6 N18 C19 O21 -10.9(5) . . . . ? O20 C19 O21 C22 4.2(5) . . . . ? N18 C19 O21 C22 -175.1(3) . . . . ? C19 O21 C22 C23 -179.2(3) . . . . ? O21 C22 C23 C24 172.9(3) . . . . ? O21 C22 C23 C28 -8.5(5) . . . . ? C28 C23 C24 C25 0.0(6) . . . . ? C22 C23 C24 C25 178.7(4) . . . . ? C23 C24 C25 C26 -0.3(7) . . . . ? C24 C25 C26 C27 0.6(7) . . . . ? C25 C26 C27 C28 -0.5(7) . . . . ? C26 C27 C28 C23 0.1(6) . . . . ? C24 C23 C28 C27 0.1(6) . . . . ? C22 C23 C28 C27 -178.5(4) . . . . ? C34 O29 C30 C31 -60.2(4) . . . . ? O29 C30 C31 C32 56.7(5) . . . . ? C30 C31 C32 C33 -53.3(5) . . . . ? C31 C32 C33 C34 50.8(5) . . . . ? C30 O29 C34 N46 -61.4(4) . . . . ? C30 O29 C34 C33 56.9(4) . . . . ? C30 O29 C34 C35 179.5(3) . . . . ? C32 C33 C34 O29 -51.7(4) . . . . ? C32 C33 C34 N46 70.2(4) . . . . ? C32 C33 C34 C35 -168.9(3) . . . . ? O29 C34 C35 O38 179.0(3) . . . . ? N46 C34 C35 O38 58.5(4) . . . . ? C33 C34 C35 O38 -60.2(4) . . . . ? O29 C34 C35 C36 -58.2(4) . . . . ? N46 C34 C35 C36 -178.7(3) . . . . ? C33 C34 C35 C36 62.6(4) . . . . ? O38 C35 C36 C37 9.2(7) . . . . ? C34 C35 C36 C37 -111.2(5) . . . . ? C36 C35 O38 Si39 103.3(4) . . . . ? C34 C35 O38 Si39 -134.3(3) . . . . ? C35 O38 Si39 C40 -70.4(3) . . . . ? C35 O38 Si39 C41 50.0(3) . . . . ? C35 O38 Si39 C45 170.3(3) . . . . ? O38 Si39 C45 C43 -61.5(4) . . . . ? C40 Si39 C45 C43 179.5(4) . . . . ? C41 Si39 C45 C43 57.7(4) . . . . ? O38 Si39 C45 C44 178.1(3) . . . . ? C40 Si39 C45 C44 59.1(4) . . . . ? C41 Si39 C45 C44 -62.6(4) . . . . ? O38 Si39 C45 C42 59.7(4) . . . . ? C40 Si39 C45 C42 -59.3(4) . . . . ? C41 Si39 C45 C42 179.0(3) . . . . ? O29 C34 N46 C47 -47.4(5) . . . . ? C33 C34 N46 C47 -168.5(4) . . . . ? C35 C34 N46 C47 68.4(5) . . . . ? C34 N46 C47 O48 -176.0(4) . . . . ? C34 N46 C47 O49 5.4(5) . . . . ? O48 C47 O49 C50 -7.9(5) . . . . ? N46 C47 O49 C50 170.7(3) . . . . ? C47 O49 C50 C51 -174.0(3) . . . . ? O49 C50 C51 C52 -157.1(4) . . . . ? O49 C50 C51 C56 23.5(6) . . . . ? C56 C51 C52 C53 -0.2(6) . . . . ? C50 C51 C52 C53 -179.6(4) . . . . ? C51 C52 C53 C54 0.7(7) . . . . ? C52 C53 C54 C55 -0.5(7) . . . . ? C53 C54 C55 C56 -0.2(7) . . . . ? C54 C55 C56 C51 0.6(7) . . . . ? C52 C51 C56 C55 -0.4(6) . . . . ? C50 C51 C56 C55 178.9(4) . . . . ? 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 N18 H18 O48 0.88 2.04 2.917(4) 170.9 . N46 H46 O20 0.88 1.99 2.858(4) 171.3 . _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 25.11 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 1.200 _refine_diff_density_min -0.317 _refine_diff_density_rms 0.085