data_global _journal_name_full Org.Biomol.Chem. _journal_coden_Cambridge 0177 _publ_contact_author_name 'Stephen G. Davies' _publ_contact_author_address ;Department of Organic Chemistry, University of Oxford, Chemistry Research Laboratory, Mansfield Road, Oxford, OX1 3TA, UK. ; _publ_contact_author_email steve.davies@chem.ox.ac.uk _publ_contact_author_phone '+44 1865 275646' _publ_contact_author_fax '+44 1865 275633' loop_ _publ_author_name _publ_author_address A.Naylor ;Department of Medicinal Chemistry, Neurology and Gastrointestinal Diseases Centre of Excellence for Drug Discovery, GlaxoSmithKline, New Frontiers Science Park, Third Avenue, Harlow, Essex, CM19 5AW, UK. ; J.W.B.Cooke ;Department of Organic Chemistry, University of Oxford, Chemistry Research Laboratory, Mansfield Road, Oxford, OX1 3TA, UK. ; S.G.Davies ;Department of Organic Chemistry, University of Oxford, Chemistry Research Laboratory, Mansfield Road, Oxford, OX1 3TA, UK. ; K.B.Ling ;Department of Organic Chemistry, University of Oxford, Chemistry Research Laboratory, Mansfield Road, Oxford, OX1 3TA, UK. ; R.L.Nicholson ;Department of Organic Chemistry, University of Oxford, Chemistry Research Laboratory, Mansfield Road, Oxford, OX1 3TA, UK. ; ; P.D.Price ; ;Department of Organic Chemistry, University of Oxford, Chemistry Research Laboratory, Mansfield Road, Oxford, OX1 3TA, UK. ; 'P.M.Roberts ' ;Department of Organic Chemistry, University of Oxford, Chemistry Research Laboratory, Mansfield Road, Oxford, OX1 3TA, UK. ; A.D.Smith ;Department of Organic Chemistry, University of Oxford, Chemistry Research Laboratory, Mansfield Road, Oxford, OX1 3TA, UK. ; J.E.Thomson ;Department of Organic Chemistry, University of Oxford, Chemistry Research Laboratory, Mansfield Road, Oxford, OX1 3TA, UK. ; _publ_section_references ; User-defined structure solution reference Betteridge, P.W., Carruthers, J.R., Cooper, R.I., Prout, K., & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. Nonius (1997-2001). COLLECT. Nonius BV, Delft, The Netherlands. Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, edited by C. W. Carter Jr & R. M. Sweet, pp. 307--326. New York: Academic Press. Prince, E. Mathematical Techniques in Crystallography and Materials Science Springer-Verlag, New York, 1982. Watkin D.J. (1994). Acta Cryst, A50, 411-437 Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996). CAMERON, Chemical Crystallography Laboratory, OXFORD, UK. ; _publ_contact_letter ; Please consider this CIF submission for publication as a Short Format Paper in Org. Biomol. Chem. The figures have been sent by mail. ; _publ_requested_category CO # choose from: FI FM FO CI CM CO AD _publ_requested_coeditor_name 'Dr Paul M. Roberts' _publ_section_title # Title of paper ; Asymmetric synthesis of beta-amino-gamma-substituted-gamma-butyrolactones: double diastereoselective conjugate addition of homochiral lithium amides to homochiral gamma-silyloxy-alpha,beta-unsaturated esters ; _publ_section_exptl_refinement # Some potentially useful phrases are: ; Because the data were collected with molybdenum radiation, there were no measurable anomalous differences, as a consequence of which it was admissible to merge Friedel pairs of reflections. All hydrogen atoms were found in difference density syntheses. Hydrogen atoms were placed geometrically after each cycle. Hydrogen atoms were placed geometrically after each cycle, the preferred orientations of those groups whose conformations could not be assigned unambiguously having been previously identified by examination of a difference Fourier map. Hydrogen atoms were seen in a difference density synthesis. Those attached to carbon atoms were repositioned geometrically. Hydrogen were initially refined with soft restraints on the bonds to regularise their geometry (bond lengths to accepted values, angles either set by symmetry or to accepted values, and U[iso] dependent upon the adjacent bonded atom), after which they were refined with riding constraints only. donated by Bill Clegg: The H atoms were all located in a difference map, but those attached to carbon atoms were repositioned geometrically. The H atoms were initially refined with soft restraints on the bond lengths and angles to regularise their geometry (C---H in the range 0.93-98, O---N in the range 0.86-0.89 and O---H = 0.82 \%A) and isotropic adps (U(H) in the range 1.2-1.5 times U~equiv~ of the adjacent atom), after which they were refined with riding constraints. . ; data_1 _database_code_depnum_ccdc_archive 'CCDC 634215' _audit_creation_date 06-08-25 _audit_creation_method CRYSTALS_ver_12.82 _oxford_structure_analysis_title '8250950 SGD155' _chemical_name_systematic ? _chemical_melting_point ? _cell_length_a 11.4449(2) _cell_length_b 11.8000(2) _cell_length_c 14.6478(2) _cell_angle_alpha 71.9010(6) _cell_angle_beta 67.6483(7) _cell_angle_gamma 76.2070(8) _cell_volume 1722.68(5) _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P 1' _symmetry_int_tables_number 1 _symmetry_space_group_name_Hall ? loop_ _symmetry_equiv_pos_as_xyz x,y,z loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4' H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4' N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826 -11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4' O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4' Si 0.0817 0.0704 6.2915 2.4386 3.0353 32.3337 1.9891 0.6785 1.5410 81.6937 1.1407 'International Tables Vol C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 2 # Given Formula = C36 H51 N1 O3 Si1 # Dc = 1.11 Fooo = 624.00 Mu = 1.01 M = 1147.78 # Found Formula = C36 H51 N1 O3 Si1 # Dc = 1.11 FOOO = 624.00 Mu = 1.01 M = 1147.78 _chemical_formula_sum 'C36 H51 N1 O3 Si1' _chemical_formula_moiety 'C36 H51 N1 O3 Si1' _chemical_compound_source ? _chemical_formula_weight 573.89 _cell_measurement_reflns_used 7262 _cell_measurement_theta_min 5 _cell_measurement_theta_max 27 _cell_measurement_temperature 190 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_min 0.10 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_max 0.10 _exptl_crystal_density_diffrn 1.106 _exptl_crystal_density_meas ? # Non-dispersive F(000): _exptl_crystal_F_000 624 _exptl_absorpt_coefficient_mu 0.101 # Sheldrick geometric approximatio 0.99 0.99 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _exptl_absorpt_correction_T_min 0.99 _exptl_absorpt_correction_T_max 0.99 _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_radiation_monochromator graphite _diffrn_radiation_probe ? _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_method \w _computing_data_collection 'COLLECT. Nonius (1997-2001).' _computing_data_reduction 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_cell_refinement 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_structure_solution 'USER DEFINED STRUCTURE SOLUTION' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_publication_material 'CRYSTALS (Betteridge et al., 2003)' _computing_molecular_graphics 'CAMERON (Watkin et al., 1996)' _diffrn_standards_interval_time ? _diffrn_standards_interval_count ? _diffrn_standards_number 0 _diffrn_standards_decay_% ? _diffrn_ambient_temperature 190 _diffrn_reflns_number 14183 _reflns_number_total 7805 _diffrn_reflns_av_R_equivalents 0.025 # Number of reflections with Friedels Law is 7805 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 7963 _diffrn_reflns_theta_min 5.175 _diffrn_reflns_theta_max 27.560 _diffrn_measured_fraction_theta_max 0.981 _diffrn_reflns_theta_full 26.457 _diffrn_measured_fraction_theta_full 0.989 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 18 _reflns_limit_h_min -13 _reflns_limit_h_max 14 _reflns_limit_k_min -14 _reflns_limit_k_max 15 _reflns_limit_l_min 0 _reflns_limit_l_max 19 _oxford_diffrn_Wilson_B_factor 0.00 _oxford_diffrn_Wilson_scale 0.00 _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.87 _refine_diff_density_max 0.96 _refine_ls_number_reflns 6098 _refine_ls_number_restraints 3 _refine_ls_number_parameters 739 _refine_ls_R_factor_ref 0.0668 _refine_ls_wR_factor_ref 0.0822 _refine_ls_goodness_of_fit_ref 1.1046 _reflns_number_all 7805 _refine_ls_R_factor_all 0.0847 _refine_ls_wR_factor_all 0.1030 # The I/u(I) cutoff below was used for refinement as # well as the _gt R-factors: _reflns_threshold_expression I>2.00u(I) _reflns_number_gt 6098 _refine_ls_R_factor_gt 0.0668 _refine_ls_wR_factor_gt 0.0822 _refine_ls_shift/su_max 0.000874 _chemical_absolute_configuration unk _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_hydrogen_treatment constr # none, undef, noref, refall, # refxyz, refU, constr or mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ A~i~ are: 1.13 0.753 0.606 ; _refine_special_details ; There are two molecules in the asymmetric unit: one of these is well defined but the other suffers from disorder of the tert-butyl group in the TBDMS moiety which has resulted in the C(5)-C(6) Csp3-Csp3 bond length being 1.99 Angstroms. ; 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_occupancy _atom_site_adp_type _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_attached_hydrogens C1 C 0.7302(4) 0.1193(4) 0.5747(3) 0.0352 1.0000 Uani . . . . . . C2 C 0.6518(4) 0.0627(3) 0.5380(3) 0.0350 1.0000 Uani . . . . . . O3 O 0.7396(3) -0.0167(3) 0.4785(2) 0.0431 1.0000 Uani . . . . . . Si4 Si 0.70971(18) -0.0916(3) 0.4142(2) 0.1206 1.0000 Uani . . . . . . C5 C 0.8020(11) -0.092(3) 0.3026(14) 0.3184 1.0000 Uani . . . . . . C6 C 0.7101(9) 0.0689(8) 0.2570(7) 0.1041 1.0000 Uani . . . . . . C7 C 0.9395(8) -0.0738(17) 0.2643(10) 0.1943 1.0000 Uani . . . . . . C8 C 0.5427(5) -0.1107(8) 0.4538(6) 0.0846 1.0000 Uani . . . . . . C9 C 0.8044(11) -0.2697(7) 0.4694(9) 0.1198 1.0000 Uani . . . . . . C10 C 0.5525(4) -0.0049(4) 0.6281(3) 0.0368 1.0000 Uani . . . . . . C11 C 0.4235(4) 0.0395(4) 0.6509(3) 0.0420 1.0000 Uani . . . . . . C12 C 0.3331(4) -0.0250(5) 0.7320(4) 0.0565 1.0000 Uani . . . . . . C13 C 0.3722(5) -0.1347(6) 0.7902(4) 0.0648 1.0000 Uani . . . . . . C14 C 0.4998(6) -0.1793(5) 0.7688(4) 0.0668 1.0000 Uani . . . . . . C15 C 0.5888(5) -0.1143(4) 0.6888(4) 0.0518 1.0000 Uani . . . . . . N16 N 0.6442(3) 0.2063(3) 0.6314(3) 0.0390 1.0000 Uani . . . . . . C17 C 0.6698(5) 0.2111(4) 0.7230(3) 0.0448 1.0000 Uani . . . . . . C18 C 0.7847(5) 0.2707(5) 0.7026(4) 0.0519 1.0000 Uani . . . . . . C19 C 0.7702(6) 0.3930(5) 0.6962(4) 0.0617 1.0000 Uani . . . . . . C20 C 0.8731(8) 0.4476(7) 0.6801(5) 0.0811 1.0000 Uani . . . . . . C21 C 0.9903(8) 0.3849(9) 0.6721(5) 0.0885 1.0000 Uani . . . . . . C22 C 1.0082(6) 0.2646(10) 0.6779(5) 0.0916 1.0000 Uani . . . . . . C23 C 0.9062(6) 0.2057(7) 0.6937(5) 0.0691 1.0000 Uani . . . . . . C24 C 0.6674(7) 0.0885(5) 0.7982(4) 0.0662 1.0000 Uani . . . . . . C25 C 0.6104(4) 0.3249(4) 0.5715(3) 0.0418 1.0000 Uani . . . . . . C26 C 0.4881(4) 0.3937(4) 0.6288(3) 0.0429 1.0000 Uani . . . . . . C27 C 0.3837(5) 0.3381(4) 0.6961(4) 0.0478 1.0000 Uani . . . . . . C28 C 0.2716(5) 0.4041(5) 0.7447(4) 0.0591 1.0000 Uani . . . . . . C29 C 0.2634(6) 0.5270(5) 0.7265(5) 0.0638 1.0000 Uani . . . . . . C30 C 0.3651(6) 0.5836(5) 0.6595(5) 0.0694 1.0000 Uani . . . . . . C31 C 0.4782(5) 0.5187(4) 0.6108(4) 0.0560 1.0000 Uani . . . . . . C32 C 0.8530(4) 0.1627(4) 0.4884(3) 0.0387 1.0000 Uani . . . . . . C33 C 0.9648(4) 0.0643(4) 0.4753(4) 0.0453 1.0000 Uani . . . . . . O34 O 0.9722(3) -0.0038(3) 0.5656(2) 0.0473 1.0000 Uani . . . . . . C35 C 1.0818(5) -0.0973(5) 0.5754(4) 0.0571 1.0000 Uani . . . . . . C36 C 1.0532(6) -0.1380(6) 0.6896(5) 0.0753 1.0000 Uani . . . . . . C37 C 1.0845(9) -0.1974(7) 0.5318(7) 0.1022 1.0000 Uani . . . . . . C38 C 1.2036(6) -0.0401(9) 0.5266(6) 0.1041 1.0000 Uani . . . . . . O39 O 1.0425(3) 0.0508(4) 0.3948(3) 0.0633 1.0000 Uani . . . . . . C40 C 0.8395(5) 0.2299(4) 0.3838(3) 0.0483 1.0000 Uani . . . . . . C41 C 0.6358(4) 0.5548(4) 0.1135(3) 0.0396 1.0000 Uani . . . . . . C42 C 0.5375(4) 0.4649(4) 0.1591(3) 0.0420 1.0000 Uani . . . . . . O43 O 0.4260(3) 0.5171(3) 0.2275(2) 0.0460 1.0000 Uani . . . . . . Si44 Si 0.31948(17) 0.44605(16) 0.32958(11) 0.0593 1.0000 Uani . . . . . . C45 C 0.1785(8) 0.4340(10) 0.3013(5) 0.1097 1.0000 Uani . . . . . . C46 C 0.0662(10) 0.4025(12) 0.4031(6) 0.1388 1.0000 Uani . . . . . . C47 C 0.2088(14) 0.3332(15) 0.2453(7) 0.1974 1.0000 Uani . . . . . . C48 C 0.1327(9) 0.5532(16) 0.2391(8) 0.1892 1.0000 Uani . . . . . . C49 C 0.2719(8) 0.5365(8) 0.4248(5) 0.0961 1.0000 Uani . . . . . . C50 C 0.3948(11) 0.2947(8) 0.3820(7) 0.1286 1.0000 Uani . . . . . . C51 C 0.5051(4) 0.4420(4) 0.0756(3) 0.0430 1.0000 Uani . . . . . . C52 C 0.4408(5) 0.5324(4) 0.0196(3) 0.0472 1.0000 Uani . . . . . . C53 C 0.4077(5) 0.5116(5) -0.0565(4) 0.0525 1.0000 Uani . . . . . . C54 C 0.4382(6) 0.3989(6) -0.0735(4) 0.0654 1.0000 Uani . . . . . . C55 C 0.5025(7) 0.3086(5) -0.0188(5) 0.0724 1.0000 Uani . . . . . . C56 C 0.5369(6) 0.3293(5) 0.0557(4) 0.0574 1.0000 Uani . . . . . . N57 N 0.7565(4) 0.4964(3) 0.0528(3) 0.0420 1.0000 Uani . . . . . . C58 C 0.8303(5) 0.5733(4) -0.0445(3) 0.0465 1.0000 Uani . . . . . . C59 C 0.8874(4) 0.6707(4) -0.0346(3) 0.0460 1.0000 Uani . . . . . . C60 C 1.0068(5) 0.6417(5) -0.0201(4) 0.0568 1.0000 Uani . . . . . . C61 C 1.0611(6) 0.7299(6) -0.0105(5) 0.0675 1.0000 Uani . . . . . . C62 C 1.0007(7) 0.8448(6) -0.0162(5) 0.0756 1.0000 Uani . . . . . . C63 C 0.8828(6) 0.8740(5) -0.0301(5) 0.0709 1.0000 Uani . . . . . . C64 C 0.8272(5) 0.7885(5) -0.0385(4) 0.0582 1.0000 Uani . . . . . . C65 C 0.7550(6) 0.6194(5) -0.1174(4) 0.0604 1.0000 Uani . . . . . . C66 C 0.8359(5) 0.4132(4) 0.1091(4) 0.0486 1.0000 Uani . . . . . . C67 C 0.9319(5) 0.3234(4) 0.0518(4) 0.0523 1.0000 Uani . . . . . . C68 C 0.9011(6) 0.2741(5) -0.0095(4) 0.0580 1.0000 Uani . . . . . . C69 C 0.9906(7) 0.1873(5) -0.0558(5) 0.0695 1.0000 Uani . . . . . . C70 C 1.1070(7) 0.1525(5) -0.0435(6) 0.0796 1.0000 Uani . . . . . . C71 C 1.1392(7) 0.2032(6) 0.0164(6) 0.0821 1.0000 Uani . . . . . . C72 C 1.0502(6) 0.2894(5) 0.0618(5) 0.0686 1.0000 Uani . . . . . . C73 C 0.6418(5) 0.6121(4) 0.1945(3) 0.0451 1.0000 Uani . . . . . . C74 C 0.5324(4) 0.7143(4) 0.2171(3) 0.0420 1.0000 Uani . . . . . . O75 O 0.5078(3) 0.7806(3) 0.1319(2) 0.0461 1.0000 Uani . . . . . . C76 C 0.4129(5) 0.8890(4) 0.1330(4) 0.0525 1.0000 Uani . . . . . . C77 C 0.4149(8) 0.9264(7) 0.0226(5) 0.0901 1.0000 Uani . . . . . . C78 C 0.2837(6) 0.8602(7) 0.2043(6) 0.0873 1.0000 Uani . . . . . . C79 C 0.4564(8) 0.9826(5) 0.1579(8) 0.0939 1.0000 Uani . . . . . . O80 O 0.4807(4) 0.7355(3) 0.2990(3) 0.0576 1.0000 Uani . . . . . . C81 C 0.6539(6) 0.5270(5) 0.2939(4) 0.0631 1.0000 Uani . . . . . . C82 C 0.7859(8) -0.1859(15) 0.2542(9) 0.1714 1.0000 Uani . . . . . . H11 H 0.7587 0.0526 0.6252 0.0420 1.0000 Uiso R . . . . . H21 H 0.6106 0.1297 0.4947 0.0462 1.0000 Uiso R . . . . . H111 H 0.3972 0.1129 0.6116 0.0552 1.0000 Uiso R . . . . . H121 H 0.2460 0.0052 0.7466 0.0726 1.0000 Uiso R . . . . . H131 H 0.3114 -0.1787 0.8462 0.0822 1.0000 Uiso R . . . . . H141 H 0.5259 -0.2544 0.8080 0.0792 1.0000 Uiso R . . . . . H151 H 0.6765 -0.1448 0.6746 0.0615 1.0000 Uiso R . . . . . H171 H 0.5938 0.2635 0.7586 0.0618 1.0000 Uiso R . . . . . H191 H 0.6879 0.4375 0.7035 0.0834 1.0000 Uiso R . . . . . H201 H 0.8618 0.5316 0.6728 0.1073 1.0000 Uiso R . . . . . H211 H 1.0596 0.4208 0.6643 0.1242 1.0000 Uiso R . . . . . H221 H 1.0902 0.2202 0.6703 0.1206 1.0000 Uiso R . . . . . H231 H 0.9177 0.1220 0.6990 0.0914 1.0000 Uiso R . . . . . H241 H 0.6716 0.0965 0.8610 0.1029 1.0000 Uiso R . . . . . H242 H 0.7409 0.0340 0.7691 0.1033 1.0000 Uiso R . . . . . H243 H 0.5894 0.0576 0.8126 0.1034 1.0000 Uiso R . . . . . H251 H 0.6823 0.3719 0.5495 0.0501 1.0000 Uiso R . . . . . H252 H 0.5994 0.3143 0.5106 0.0501 1.0000 Uiso R . . . . . H271 H 0.3897 0.2539 0.7084 0.0635 1.0000 Uiso R . . . . . H281 H 0.2009 0.3627 0.7917 0.0782 1.0000 Uiso R . . . . . H291 H 0.1881 0.5721 0.7602 0.0794 1.0000 Uiso R . . . . . H301 H 0.3585 0.6677 0.6458 0.0865 1.0000 Uiso R . . . . . H311 H 0.5494 0.5579 0.5654 0.0723 1.0000 Uiso R . . . . . H321 H 0.8760 0.2224 0.5123 0.0492 1.0000 Uiso R . . . . . H361 H 1.1162 -0.2059 0.7029 0.1100 1.0000 Uiso R . . . . . H362 H 1.0572 -0.0727 0.7152 0.1104 1.0000 Uiso R . . . . . H363 H 0.9681 -0.1626 0.7209 0.1102 1.0000 Uiso R . . . . . H371 H 1.1528 -0.2598 0.5443 0.1712 1.0000 Uiso R . . . . . H372 H 1.0022 -0.2268 0.5665 0.1713 1.0000 Uiso R . . . . . H373 H 1.1007 -0.1647 0.4593 0.1711 1.0000 Uiso R . . . . . H381 H 1.2736 -0.1023 0.5336 0.1501 1.0000 Uiso R . . . . . H382 H 1.1951 0.0199 0.5628 0.1503 1.0000 Uiso R . . . . . H383 H 1.2126 -0.0037 0.4551 0.1502 1.0000 Uiso R . . . . . H401 H 0.9236 0.2414 0.3332 0.0753 1.0000 Uiso R . . . . . H402 H 0.7881 0.3076 0.3857 0.0752 1.0000 Uiso R . . . . . H403 H 0.7988 0.1819 0.3637 0.0752 1.0000 Uiso R . . . . . H411 H 0.6021 0.6213 0.0661 0.0526 1.0000 Uiso R . . . . . H421 H 0.5754 0.3883 0.1959 0.0560 1.0000 Uiso R . . . . . H461 H -0.0110 0.4079 0.3885 0.2371 1.0000 Uiso R . . . . . H462 H 0.0550 0.4579 0.4437 0.2371 1.0000 Uiso R . . . . . H463 H 0.0893 0.3209 0.4384 0.2371 1.0000 Uiso R . . . . . H471 H 0.1323 0.3150 0.2430 0.3341 1.0000 Uiso R . . . . . H472 H 0.2485 0.2653 0.2850 0.3342 1.0000 Uiso R . . . . . H473 H 0.2681 0.3575 0.1774 0.3340 1.0000 Uiso R . . . . . H481 H 0.0476 0.5532 0.2416 0.2420 1.0000 Uiso R . . . . . H482 H 0.1330 0.6144 0.2703 0.2422 1.0000 Uiso R . . . . . H483 H 0.1878 0.5681 0.1693 0.2420 1.0000 Uiso R . . . . . H491 H 0.2310 0.4886 0.4925 0.1421 1.0000 Uiso R . . . . . H492 H 0.3466 0.5641 0.4223 0.1422 1.0000 Uiso R . . . . . H493 H 0.2108 0.6041 0.4055 0.1421 1.0000 Uiso R . . . . . H521 H 0.4194 0.6098 0.0323 0.0614 1.0000 Uiso R . . . . . H531 H 0.3642 0.5755 -0.0949 0.0693 1.0000 Uiso R . . . . . H541 H 0.4153 0.3833 -0.1240 0.0873 1.0000 Uiso R . . . . . H551 H 0.5231 0.2314 -0.0314 0.0956 1.0000 Uiso R . . . . . H561 H 0.5812 0.2667 0.0938 0.0765 1.0000 Uiso R . . . . . H581 H 0.9057 0.5187 -0.0758 0.0624 1.0000 Uiso R . . . . . H601 H 1.0471 0.5611 -0.0166 0.0665 1.0000 Uiso R . . . . . H611 H 1.1425 0.7107 -0.0021 0.0840 1.0000 Uiso R . . . . . H621 H 1.0362 0.9029 -0.0085 0.0962 1.0000 Uiso R . . . . . H631 H 0.8396 0.9538 -0.0345 0.0844 1.0000 Uiso R . . . . . H641 H 0.7469 0.8102 -0.0474 0.0704 1.0000 Uiso R . . . . . H651 H 0.8102 0.6553 -0.1843 0.1030 1.0000 Uiso R . . . . . H652 H 0.6849 0.6810 -0.0932 0.1033 1.0000 Uiso R . . . . . H653 H 0.7206 0.5528 -0.1205 0.1035 1.0000 Uiso R . . . . . H661 H 0.8837 0.4602 0.1238 0.0651 1.0000 Uiso R . . . . . H662 H 0.7793 0.3695 0.1735 0.0652 1.0000 Uiso R . . . . . H681 H 0.8198 0.2978 -0.0184 0.0774 1.0000 Uiso R . . . . . H691 H 0.9687 0.1526 -0.0951 0.0834 1.0000 Uiso R . . . . . H701 H 1.1670 0.0941 -0.0764 0.0921 1.0000 Uiso R . . . . . H711 H 1.2195 0.1796 0.0256 0.0992 1.0000 Uiso R . . . . . H721 H 1.0702 0.3237 0.1028 0.0861 1.0000 Uiso R . . . . . H731 H 0.7198 0.6518 0.1610 0.0641 1.0000 Uiso R . . . . . H771 H 0.3395 0.9843 0.0198 0.1251 1.0000 Uiso R . . . . . H772 H 0.4922 0.9614 -0.0196 0.1254 1.0000 Uiso R . . . . . H773 H 0.4131 0.8553 0.0036 0.1254 1.0000 Uiso R . . . . . H781 H 0.2207 0.9277 0.1921 0.1271 1.0000 Uiso R . . . . . H782 H 0.2853 0.8441 0.2733 0.1271 1.0000 Uiso R . . . . . H783 H 0.2688 0.7897 0.1918 0.1275 1.0000 Uiso R . . . . . H791 H 0.4063 1.0603 0.1424 0.1540 1.0000 Uiso R . . . . . H792 H 0.5457 0.9878 0.1181 0.1540 1.0000 Uiso R . . . . . H793 H 0.4446 0.9562 0.2304 0.1542 1.0000 Uiso R . . . . . H811 H 0.6332 0.5736 0.3432 0.1062 1.0000 Uiso R . . . . . H812 H 0.7404 0.4851 0.2831 0.1061 1.0000 Uiso R . . . . . H813 H 0.5937 0.4685 0.3180 0.1061 1.0000 Uiso R . . . . . H821 H 0.8450 -0.1846 0.1866 0.3101 1.0000 Uiso R . . . . . H822 H 0.7990 -0.2630 0.2995 0.3101 1.0000 Uiso R . . . . . H823 H 0.7000 -0.1741 0.2522 0.3099 1.0000 Uiso R . . . . . H81 H 0.5310 -0.1563 0.4114 0.1217 1.0000 Uiso R . . . . . H82 H 0.5152 -0.1561 0.5269 0.1217 1.0000 Uiso R . . . . . H83 H 0.4898 -0.0297 0.4461 0.1217 1.0000 Uiso R . . . . . H91 H 0.7956 -0.3282 0.4362 0.1546 1.0000 Uiso R . . . . . H92 H 0.8967 -0.2634 0.4504 0.1546 1.0000 Uiso R . . . . . H93 H 0.7670 -0.2984 0.5450 0.1546 1.0000 Uiso R . . . . . H71 H 0.9770 -0.0716 0.1901 0.2380 1.0000 Uiso R . . . . . H72 H 0.9845 -0.1440 0.3030 0.2380 1.0000 Uiso R . . . . . H73 H 0.9498 0.0024 0.2753 0.2380 1.0000 Uiso R . . . . . H61 H 0.7484 0.1007 0.1818 0.1343 1.0000 Uiso R . . . . . H62 H 0.7149 0.1260 0.2931 0.1343 1.0000 Uiso R . . . . . H63 H 0.6188 0.0601 0.2741 0.1343 1.0000 Uiso R . . . . . H501 H 0.3304 0.2520 0.4436 0.1313 1.0000 Uiso R . . . . . H502 H 0.4678 0.3015 0.4008 0.1313 1.0000 Uiso R . . . . . H503 H 0.4268 0.2483 0.3285 0.1313 1.0000 Uiso 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 C1 0.0362(18) 0.036(2) 0.0331(18) 0.0003(15) -0.0155(15) -0.0080(15) C2 0.0345(18) 0.0320(18) 0.0370(19) -0.0071(15) -0.0130(15) -0.0019(15) O3 0.0354(14) 0.0468(16) 0.0475(16) -0.0187(13) -0.0055(12) -0.0105(12) Si4 0.0529(9) 0.194(3) 0.155(2) -0.145(2) 0.0272(11) -0.0550(12) C5 0.116(8) 0.70(5) 0.279(19) -0.40(3) 0.105(11) -0.217(18) C6 0.121(7) 0.089(5) 0.102(6) 0.016(4) -0.067(5) -0.017(5) C7 0.063(4) 0.41(2) 0.167(10) -0.206(14) 0.049(5) -0.110(8) C8 0.049(3) 0.132(6) 0.095(5) -0.069(5) -0.003(3) -0.032(3) C9 0.158(9) 0.059(4) 0.157(9) -0.006(5) -0.089(8) -0.006(5) C10 0.0358(18) 0.038(2) 0.040(2) -0.0099(16) -0.0145(16) -0.0093(16) C11 0.036(2) 0.047(2) 0.044(2) -0.0139(18) -0.0147(17) -0.0028(17) C12 0.037(2) 0.081(4) 0.055(3) -0.025(3) -0.0071(19) -0.017(2) C13 0.057(3) 0.081(4) 0.053(3) -0.003(3) -0.010(2) -0.035(3) C14 0.070(3) 0.064(3) 0.062(3) 0.019(3) -0.034(3) -0.027(3) C15 0.045(2) 0.048(3) 0.057(3) 0.001(2) -0.018(2) -0.014(2) N16 0.0498(19) 0.0373(17) 0.0352(16) -0.0080(14) -0.0213(15) -0.0045(15) C17 0.059(3) 0.042(2) 0.036(2) -0.0077(17) -0.0215(19) -0.0052(19) C18 0.052(3) 0.069(3) 0.042(2) -0.020(2) -0.018(2) -0.009(2) C19 0.073(3) 0.067(3) 0.052(3) -0.016(2) -0.024(2) -0.018(3) C20 0.100(5) 0.096(5) 0.063(4) -0.018(3) -0.026(3) -0.044(4) C21 0.089(5) 0.145(7) 0.053(3) -0.025(4) -0.018(3) -0.062(5) C22 0.059(3) 0.167(8) 0.069(4) -0.042(5) -0.034(3) -0.012(4) C23 0.063(3) 0.094(4) 0.064(3) -0.030(3) -0.034(3) 0.002(3) C24 0.100(4) 0.062(3) 0.039(2) -0.001(2) -0.030(3) -0.019(3) C25 0.055(2) 0.032(2) 0.041(2) -0.0059(16) -0.0209(18) -0.0065(17) C26 0.052(2) 0.036(2) 0.046(2) -0.0076(17) -0.0262(19) -0.0028(18) C27 0.054(2) 0.038(2) 0.056(3) -0.0116(19) -0.025(2) -0.0028(18) C28 0.049(3) 0.068(3) 0.067(3) -0.022(3) -0.024(2) -0.006(2) C29 0.064(3) 0.052(3) 0.070(3) -0.019(3) -0.025(3) 0.013(2) C30 0.078(4) 0.044(3) 0.082(4) -0.016(3) -0.030(3) 0.003(3) C31 0.064(3) 0.039(2) 0.060(3) -0.005(2) -0.022(2) -0.006(2) C32 0.042(2) 0.040(2) 0.0366(19) -0.0020(16) -0.0157(16) -0.0136(17) C33 0.037(2) 0.057(3) 0.045(2) -0.0097(19) -0.0138(18) -0.0160(18) O34 0.0349(14) 0.0551(18) 0.0446(16) -0.0068(14) -0.0133(12) -0.0001(13) C35 0.042(2) 0.069(3) 0.061(3) -0.021(3) -0.024(2) 0.007(2) C36 0.065(3) 0.074(4) 0.072(4) -0.005(3) -0.031(3) 0.013(3) C37 0.135(7) 0.072(4) 0.121(6) -0.047(5) -0.079(6) 0.038(4) C38 0.041(3) 0.162(8) 0.097(5) -0.006(5) -0.027(3) -0.020(4) O39 0.0438(17) 0.089(3) 0.0476(19) -0.0172(18) -0.0082(15) -0.0021(17) C40 0.051(2) 0.048(2) 0.041(2) 0.0002(18) -0.0160(19) -0.0139(19) C41 0.057(2) 0.0331(19) 0.0350(19) -0.0071(15) -0.0239(18) -0.0044(17) C42 0.060(3) 0.034(2) 0.0356(19) -0.0061(16) -0.0219(18) -0.0062(18) O43 0.0599(18) 0.0436(16) 0.0334(14) -0.0047(12) -0.0122(13) -0.0168(14) Si44 0.0854(10) 0.0635(9) 0.0337(6) -0.0015(6) -0.0163(6) -0.0379(8) C45 0.111(6) 0.192(9) 0.047(3) -0.007(4) -0.012(3) -0.112(6) C46 0.137(7) 0.250(13) 0.057(4) -0.035(6) 0.009(4) -0.149(9) C47 0.248(14) 0.323(18) 0.085(5) -0.091(9) 0.026(7) -0.235(15) C48 0.083(5) 0.36(2) 0.093(6) 0.070(9) -0.049(5) -0.102(9) C49 0.111(5) 0.131(6) 0.055(3) -0.042(4) 0.013(3) -0.073(5) C50 0.163(9) 0.089(6) 0.090(6) 0.043(5) -0.033(6) -0.040(6) C51 0.057(2) 0.041(2) 0.036(2) -0.0110(17) -0.0162(18) -0.0131(19) C52 0.059(3) 0.043(2) 0.043(2) -0.0098(18) -0.017(2) -0.011(2) C53 0.057(3) 0.059(3) 0.047(2) -0.011(2) -0.024(2) -0.010(2) C54 0.078(4) 0.074(4) 0.062(3) -0.029(3) -0.029(3) -0.017(3) C55 0.105(5) 0.056(3) 0.076(4) -0.034(3) -0.035(3) -0.015(3) C56 0.080(3) 0.041(2) 0.062(3) -0.017(2) -0.034(3) -0.005(2) N57 0.058(2) 0.0323(17) 0.0390(18) -0.0071(14) -0.0217(16) -0.0045(15) C58 0.056(3) 0.043(2) 0.039(2) -0.0112(18) -0.0133(19) -0.0079(19) C59 0.051(2) 0.041(2) 0.042(2) -0.0050(18) -0.0153(18) -0.0051(18) C60 0.047(3) 0.055(3) 0.061(3) -0.004(2) -0.019(2) -0.005(2) C61 0.057(3) 0.078(4) 0.071(4) -0.010(3) -0.024(3) -0.022(3) C62 0.083(4) 0.067(4) 0.088(4) -0.025(3) -0.026(3) -0.027(3) C63 0.075(4) 0.045(3) 0.093(4) -0.019(3) -0.030(3) -0.003(3) C64 0.059(3) 0.044(3) 0.071(3) -0.007(2) -0.029(3) -0.003(2) C65 0.083(4) 0.061(3) 0.043(2) -0.003(2) -0.029(2) -0.019(3) C66 0.066(3) 0.038(2) 0.048(2) -0.0134(19) -0.027(2) -0.001(2) C67 0.068(3) 0.037(2) 0.055(3) -0.0112(19) -0.028(2) -0.001(2) C68 0.075(3) 0.046(3) 0.059(3) -0.013(2) -0.029(3) -0.005(2) C69 0.099(5) 0.048(3) 0.063(3) -0.024(2) -0.022(3) -0.008(3) C70 0.084(4) 0.046(3) 0.095(5) -0.023(3) -0.025(4) 0.016(3) C71 0.077(4) 0.066(4) 0.107(5) -0.029(4) -0.045(4) 0.017(3) C72 0.078(4) 0.056(3) 0.086(4) -0.024(3) -0.048(3) 0.008(3) C73 0.060(3) 0.041(2) 0.045(2) -0.0159(18) -0.027(2) -0.0038(19) C74 0.053(2) 0.035(2) 0.041(2) -0.0101(17) -0.0165(18) -0.0089(17) O75 0.0526(17) 0.0333(14) 0.0447(16) -0.0073(12) -0.0157(13) 0.0042(12) C76 0.048(2) 0.044(2) 0.056(3) -0.009(2) -0.015(2) 0.0029(19) C77 0.097(5) 0.079(4) 0.069(4) -0.010(3) -0.036(4) 0.037(4) C78 0.045(3) 0.088(5) 0.096(5) 0.003(4) -0.009(3) -0.006(3) C79 0.101(5) 0.039(3) 0.155(7) -0.024(4) -0.063(5) 0.000(3) O80 0.069(2) 0.062(2) 0.0468(18) -0.0246(16) -0.0178(16) -0.0044(17) C81 0.103(4) 0.052(3) 0.047(3) -0.016(2) -0.047(3) 0.008(3) C82 0.077(5) 0.346(19) 0.163(9) -0.203(12) 0.021(5) -0.073(8) _refine_ls_extinction_method None _oxford_refine_ls_scale 0.924(2) loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag C1 . C2 . 1.555(5) yes C1 . N16 . 1.462(5) yes C1 . C32 . 1.557(5) yes C1 . H11 . 0.986 no C2 . O3 . 1.429(5) yes C2 . C10 . 1.519(5) yes C2 . H21 . 0.994 no O3 . Si4 . 1.641(3) yes Si4 . C5 . 1.574(11) yes Si4 . C8 . 1.823(6) yes Si4 . C9 . 2.184(9) yes C5 . C7 . 1.502(11) yes C5 . C82 . 1.563(13) yes C5 . C6 . 1.99(3) yes C6 . H61 . 1.000 no C6 . H62 . 1.000 no C6 . H63 . 1.000 no C7 . H71 . 1.000 no C7 . H72 . 1.000 no C7 . H73 . 1.000 no C8 . H81 . 1.000 no C8 . H82 . 1.000 no C8 . H83 . 1.000 no C9 . H91 . 1.000 no C9 . H92 . 1.000 no C9 . H93 . 1.000 no C10 . C11 . 1.389(6) yes C10 . C15 . 1.393(6) yes C11 . C12 . 1.393(7) yes C11 . H111 . 0.932 no C12 . C13 . 1.390(9) yes C12 . H121 . 0.938 no C13 . C14 . 1.376(8) yes C13 . H131 . 0.949 no C14 . C15 . 1.380(7) yes C14 . H141 . 0.945 no C15 . H151 . 0.946 no N16 . C17 . 1.498(5) yes N16 . C25 . 1.455(5) yes C17 . C18 . 1.525(7) yes C17 . C24 . 1.521(7) yes C17 . H171 . 1.004 no C18 . C19 . 1.390(8) yes C18 . C23 . 1.399(8) yes C19 . C20 . 1.384(9) yes C19 . H191 . 0.947 no C20 . C21 . 1.350(12) yes C20 . H201 . 0.945 no C21 . C22 . 1.365(12) yes C21 . H211 . 0.939 no C22 . C23 . 1.407(10) yes C22 . H221 . 0.944 no C23 . H231 . 0.948 no C24 . H241 . 0.973 no C24 . H242 . 0.971 no C24 . H243 . 0.969 no C25 . C26 . 1.520(6) yes C25 . H251 . 0.997 no C25 . H252 . 0.995 no C26 . C27 . 1.380(6) yes C26 . C31 . 1.400(6) yes C27 . C28 . 1.390(7) yes C27 . H271 . 0.943 no C28 . C29 . 1.377(8) yes C28 . H281 . 0.961 no C29 . C30 . 1.363(9) yes C29 . H291 . 0.944 no C30 . C31 . 1.392(8) yes C30 . H301 . 0.939 no C31 . H311 . 0.947 no C32 . C33 . 1.505(6) yes C32 . C40 . 1.538(6) yes C32 . H321 . 1.001 no C33 . O34 . 1.340(6) yes C33 . O39 . 1.207(6) yes O34 . C35 . 1.480(6) yes C35 . C36 . 1.515(8) yes C35 . C37 . 1.497(9) yes C35 . C38 . 1.516(9) yes C36 . H361 . 0.967 no C36 . H362 . 0.972 no C36 . H363 . 0.977 no C37 . H371 . 0.967 no C37 . H372 . 0.974 no C37 . H373 . 0.970 no C38 . H381 . 0.963 no C38 . H382 . 0.976 no C38 . H383 . 0.976 no C40 . H401 . 0.975 no C40 . H402 . 0.967 no C40 . H403 . 0.981 no C41 . C42 . 1.548(6) yes C41 . N57 . 1.472(6) yes C41 . C73 . 1.566(5) yes C41 . H411 . 0.984 no C42 . O43 . 1.431(5) yes C42 . C51 . 1.518(6) yes C42 . H421 . 0.992 no O43 . Si44 . 1.658(3) yes Si44 . C45 . 1.857(7) yes Si44 . C49 . 1.858(6) yes Si44 . C50 . 1.854(9) yes C45 . C46 . 1.562(9) yes C45 . C47 . 1.549(15) yes C45 . C48 . 1.516(17) yes C46 . H461 . 0.969 no C46 . H462 . 0.970 no C46 . H463 . 0.968 no C47 . H471 . 0.965 no C47 . H472 . 0.961 no C47 . H473 . 0.967 no C48 . H481 . 0.961 no C48 . H482 . 0.968 no C48 . H483 . 0.962 no C49 . H491 . 0.973 no C49 . H492 . 0.969 no C49 . H493 . 0.975 no C50 . H501 . 1.000 no C50 . H502 . 1.000 no C50 . H503 . 1.000 no C51 . C52 . 1.376(7) yes C51 . C56 . 1.383(6) yes C52 . C53 . 1.409(6) yes C52 . H521 . 0.944 no C53 . C54 . 1.367(8) yes C53 . H531 . 0.950 no C54 . C55 . 1.366(9) yes C54 . H541 . 0.950 no C55 . C56 . 1.394(7) yes C55 . H551 . 0.943 no C56 . H561 . 0.945 no N57 . C58 . 1.488(6) yes N57 . C66 . 1.454(6) yes C58 . C59 . 1.518(7) yes C58 . C65 . 1.515(7) yes C58 . H581 . 0.993 no C59 . C60 . 1.408(7) yes C59 . C64 . 1.392(7) yes C60 . C61 . 1.398(8) yes C60 . H601 . 0.948 no C61 . C62 . 1.359(9) yes C61 . H611 . 0.951 no C62 . C63 . 1.386(9) yes C62 . H621 . 0.931 no C63 . C64 . 1.372(8) yes C63 . H631 . 0.949 no C64 . H641 . 0.941 no C65 . H651 . 0.969 no C65 . H652 . 0.981 no C65 . H653 . 0.979 no C66 . C67 . 1.527(7) yes C66 . H661 . 0.980 no C66 . H662 . 0.984 no C67 . C68 . 1.390(7) yes C67 . C72 . 1.368(8) yes C68 . C69 . 1.401(8) yes C68 . H681 . 0.952 no C69 . C70 . 1.360(10) yes C69 . H691 . 0.931 no C70 . C71 . 1.392(10) yes C70 . H701 . 0.954 no C71 . C72 . 1.388(9) yes C71 . H711 . 0.943 no C72 . H721 . 0.937 no C73 . C74 . 1.531(6) yes C73 . C81 . 1.525(6) yes C73 . H731 . 0.989 no C74 . O75 . 1.343(5) yes C74 . O80 . 1.195(5) yes O75 . C76 . 1.468(5) yes C76 . C77 . 1.530(9) yes C76 . C78 . 1.496(8) yes C76 . C79 . 1.501(9) yes C77 . H771 . 0.970 no C77 . H772 . 0.967 no C77 . H773 . 0.970 no C78 . H781 . 0.960 no C78 . H782 . 0.976 no C78 . H783 . 0.969 no C79 . H791 . 0.969 no C79 . H792 . 0.971 no C79 . H793 . 0.973 no C81 . H811 . 0.967 no C81 . H812 . 0.973 no C81 . H813 . 0.982 no C82 . H821 . 0.961 no C82 . H822 . 0.963 no C82 . H823 . 0.969 no loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C2 . C1 . N16 . 108.9(3) yes C2 . C1 . C32 . 112.7(3) yes N16 . C1 . C32 . 117.2(3) yes C2 . C1 . H11 . 104.7 no N16 . C1 . H11 . 105.8 no C32 . C1 . H11 . 106.6 no C1 . C2 . O3 . 107.4(3) yes C1 . C2 . C10 . 110.7(3) yes O3 . C2 . C10 . 110.8(3) yes C1 . C2 . H21 . 107.1 no O3 . C2 . H21 . 109.8 no C10 . C2 . H21 . 110.9 no C2 . O3 . Si4 . 127.8(3) yes O3 . Si4 . C5 . 118.9(4) yes O3 . Si4 . C8 . 114.5(2) yes C5 . Si4 . C8 . 121.2(5) yes O3 . Si4 . C9 . 99.1(4) yes C5 . Si4 . C9 . 89.6(12) yes C8 . Si4 . C9 . 104.7(4) yes Si4 . C5 . C7 . 123.9(9) yes Si4 . C5 . C82 . 116.2(11) yes C7 . C5 . C82 . 109.9(9) yes Si4 . C5 . C6 . 87.6(9) yes C7 . C5 . C6 . 104.8(17) yes C82 . C5 . C6 . 110.7(14) yes H61 . C6 . H62 . 109.5 no H61 . C6 . H63 . 109.5 no H62 . C6 . H63 . 109.5 no H61 . C6 . C5 . 110.4 no H62 . C6 . C5 . 109.7 no H63 . C6 . C5 . 108.2 no C5 . C7 . H71 . 109.5 no C5 . C7 . H72 . 107.0 no H71 . C7 . H72 . 109.5 no C5 . C7 . H73 . 111.8 no H71 . C7 . H73 . 109.5 no H72 . C7 . H73 . 109.5 no Si4 . C8 . H81 . 110.4 no Si4 . C8 . H82 . 108.7 no H81 . C8 . H82 . 109.5 no Si4 . C8 . H83 . 109.3 no H81 . C8 . H83 . 109.5 no H82 . C8 . H83 . 109.5 no Si4 . C9 . H91 . 109.6 no Si4 . C9 . H92 . 107.7 no H91 . C9 . H92 . 109.5 no Si4 . C9 . H93 . 111.1 no H91 . C9 . H93 . 109.5 no H92 . C9 . H93 . 109.5 no C2 . C10 . C11 . 120.9(4) yes C2 . C10 . C15 . 120.5(4) yes C11 . C10 . C15 . 118.5(4) yes C10 . C11 . C12 . 120.4(4) yes C10 . C11 . H111 . 119.9 no C12 . C11 . H111 . 119.7 no C11 . C12 . C13 . 119.7(4) yes C11 . C12 . H121 . 120.0 no C13 . C12 . H121 . 120.3 no C12 . C13 . C14 . 120.4(5) yes C12 . C13 . H131 . 120.3 no C14 . C13 . H131 . 119.3 no C13 . C14 . C15 . 119.5(5) yes C13 . C14 . H141 . 120.1 no C15 . C14 . H141 . 120.4 no C10 . C15 . C14 . 121.4(5) yes C10 . C15 . H151 . 119.2 no C14 . C15 . H151 . 119.4 no C1 . N16 . C17 . 116.4(3) yes C1 . N16 . C25 . 116.7(3) yes C17 . N16 . C25 . 112.8(3) yes N16 . C17 . C18 . 116.4(4) yes N16 . C17 . C24 . 110.9(4) yes C18 . C17 . C24 . 113.1(4) yes N16 . C17 . H171 . 105.1 no C18 . C17 . H171 . 105.1 no C24 . C17 . H171 . 104.9 no C17 . C18 . C19 . 120.2(5) yes C17 . C18 . C23 . 122.4(5) yes C19 . C18 . C23 . 117.4(5) yes C18 . C19 . C20 . 120.8(6) yes C18 . C19 . H191 . 118.1 no C20 . C19 . H191 . 121.2 no C19 . C20 . C21 . 121.9(7) yes C19 . C20 . H201 . 119.3 no C21 . C20 . H201 . 118.8 no C20 . C21 . C22 . 118.9(6) yes C20 . C21 . H211 . 122.2 no C22 . C21 . H211 . 118.9 no C21 . C22 . C23 . 121.0(7) yes C21 . C22 . H221 . 119.8 no C23 . C22 . H221 . 119.2 no C22 . C23 . C18 . 120.0(7) yes C22 . C23 . H231 . 121.4 no C18 . C23 . H231 . 118.6 no C17 . C24 . H241 . 109.2 no C17 . C24 . H242 . 109.0 no H241 . C24 . H242 . 109.3 no C17 . C24 . H243 . 109.7 no H241 . C24 . H243 . 109.5 no H242 . C24 . H243 . 110.1 no N16 . C25 . C26 . 113.6(3) yes N16 . C25 . H251 . 107.9 no C26 . C25 . H251 . 109.3 no N16 . C25 . H252 . 107.9 no C26 . C25 . H252 . 108.5 no H251 . C25 . H252 . 109.6 no C25 . C26 . C27 . 122.5(4) yes C25 . C26 . C31 . 119.3(4) yes C27 . C26 . C31 . 118.2(4) yes C26 . C27 . C28 . 121.1(4) yes C26 . C27 . H271 . 118.5 no C28 . C27 . H271 . 120.4 no C27 . C28 . C29 . 120.1(5) yes C27 . C28 . H281 . 119.1 no C29 . C28 . H281 . 120.8 no C28 . C29 . C30 . 119.6(5) yes C28 . C29 . H291 . 120.4 no C30 . C29 . H291 . 119.9 no C29 . C30 . C31 . 120.9(5) yes C29 . C30 . H301 . 119.5 no C31 . C30 . H301 . 119.6 no C26 . C31 . C30 . 120.0(5) yes C26 . C31 . H311 . 119.1 no C30 . C31 . H311 . 120.9 no C1 . C32 . C33 . 113.2(3) yes C1 . C32 . C40 . 116.6(3) yes C33 . C32 . C40 . 109.4(4) yes C1 . C32 . H321 . 104.6 no C33 . C32 . H321 . 106.4 no C40 . C32 . H321 . 105.7 no C32 . C33 . O34 . 111.1(4) yes C32 . C33 . O39 . 125.3(4) yes O34 . C33 . O39 . 123.4(4) yes C33 . O34 . C35 . 122.5(4) yes O34 . C35 . C36 . 102.5(4) yes O34 . C35 . C37 . 109.8(5) yes C36 . C35 . C37 . 111.8(6) yes O34 . C35 . C38 . 109.4(5) yes C36 . C35 . C38 . 109.2(5) yes C37 . C35 . C38 . 113.4(7) yes C35 . C36 . H361 . 107.6 no C35 . C36 . H362 . 110.0 no H361 . C36 . H362 . 110.3 no C35 . C36 . H363 . 108.2 no H361 . C36 . H363 . 110.0 no H362 . C36 . H363 . 110.6 no C35 . C37 . H371 . 107.8 no C35 . C37 . H372 . 107.4 no H371 . C37 . H372 . 111.0 no C35 . C37 . H373 . 107.4 no H371 . C37 . H373 . 110.7 no H372 . C37 . H373 . 112.3 no C35 . C38 . H381 . 108.2 no C35 . C38 . H382 . 107.5 no H381 . C38 . H382 . 110.6 no C35 . C38 . H383 . 107.5 no H381 . C38 . H383 . 111.1 no H382 . C38 . H383 . 111.8 no C32 . C40 . H401 . 109.8 no C32 . C40 . H402 . 111.4 no H401 . C40 . H402 . 108.9 no C32 . C40 . H403 . 109.1 no H401 . C40 . H403 . 108.9 no H402 . C40 . H403 . 108.7 no C42 . C41 . N57 . 107.9(3) yes C42 . C41 . C73 . 112.9(3) yes N57 . C41 . C73 . 117.3(3) yes C42 . C41 . H411 . 104.6 no N57 . C41 . H411 . 107.5 no C73 . C41 . H411 . 105.8 no C41 . C42 . O43 . 107.2(3) yes C41 . C42 . C51 . 110.7(3) yes O43 . C42 . C51 . 110.4(4) yes C41 . C42 . H421 . 108.2 no O43 . C42 . H421 . 110.9 no C51 . C42 . H421 . 109.5 no C42 . O43 . Si44 . 127.6(3) yes O43 . Si44 . C45 . 111.9(2) yes O43 . Si44 . C49 . 105.6(2) yes C45 . Si44 . C49 . 110.6(4) yes O43 . Si44 . C50 . 109.9(4) yes C45 . Si44 . C50 . 110.5(5) yes C49 . Si44 . C50 . 108.2(5) yes Si44 . C45 . C46 . 109.4(5) yes Si44 . C45 . C47 . 111.0(8) yes C46 . C45 . C47 . 108.1(7) yes Si44 . C45 . C48 . 110.8(6) yes C46 . C45 . C48 . 106.9(9) yes C47 . C45 . C48 . 110.5(10) yes C45 . C46 . H461 . 109.7 no C45 . C46 . H462 . 108.9 no H461 . C46 . H462 . 110.7 no C45 . C46 . H463 . 107.4 no H461 . C46 . H463 . 109.9 no H462 . C46 . H463 . 110.1 no C45 . C47 . H471 . 111.4 no C45 . C47 . H472 . 104.1 no H471 . C47 . H472 . 110.9 no C45 . C47 . H473 . 109.2 no H471 . C47 . H473 . 110.8 no H472 . C47 . H473 . 110.2 no C45 . C48 . H481 . 109.9 no C45 . C48 . H482 . 106.3 no H481 . C48 . H482 . 109.9 no C45 . C48 . H483 . 111.1 no H481 . C48 . H483 . 109.1 no H482 . C48 . H483 . 110.5 no Si44 . C49 . H491 . 110.1 no Si44 . C49 . H492 . 109.4 no H491 . C49 . H492 . 110.8 no Si44 . C49 . H493 . 105.9 no H491 . C49 . H493 . 109.5 no H492 . C49 . H493 . 111.1 no Si44 . C50 . H501 . 109.7 no Si44 . C50 . H502 . 110.5 no H501 . C50 . H502 . 109.5 no Si44 . C50 . H503 . 108.1 no H501 . C50 . H503 . 109.5 no H502 . C50 . H503 . 109.5 no C42 . C51 . C52 . 120.5(4) yes C42 . C51 . C56 . 120.8(4) yes C52 . C51 . C56 . 118.7(4) yes C51 . C52 . C53 . 121.1(4) yes C51 . C52 . H521 . 119.2 no C53 . C52 . H521 . 119.7 no C52 . C53 . C54 . 119.2(5) yes C52 . C53 . H531 . 119.8 no C54 . C53 . H531 . 121.0 no C53 . C54 . C55 . 120.2(5) yes C53 . C54 . H541 . 120.1 no C55 . C54 . H541 . 119.7 no C54 . C55 . C56 . 120.7(5) yes C54 . C55 . H551 . 119.3 no C56 . C55 . H551 . 120.0 no C55 . C56 . C51 . 120.1(5) yes C55 . C56 . H561 . 120.7 no C51 . C56 . H561 . 119.2 no C41 . N57 . C58 . 116.8(3) yes C41 . N57 . C66 . 116.2(3) yes C58 . N57 . C66 . 113.4(4) yes N57 . C58 . C59 . 115.9(4) yes N57 . C58 . C65 . 110.6(4) yes C59 . C58 . C65 . 113.4(4) yes N57 . C58 . H581 . 105.5 no C59 . C58 . H581 . 104.0 no C65 . C58 . H581 . 106.4 no C58 . C59 . C60 . 119.1(4) yes C58 . C59 . C64 . 123.2(4) yes C60 . C59 . C64 . 117.6(5) yes C59 . C60 . C61 . 120.1(5) yes C59 . C60 . H601 . 117.4 no C61 . C60 . H601 . 122.5 no C60 . C61 . C62 . 120.8(5) yes C60 . C61 . H611 . 120.1 no C62 . C61 . H611 . 119.0 no C61 . C62 . C63 . 119.4(5) yes C61 . C62 . H621 . 120.6 no C63 . C62 . H621 . 119.9 no C62 . C63 . C64 . 120.7(5) yes C62 . C63 . H631 . 120.5 no C64 . C63 . H631 . 118.8 no C59 . C64 . C63 . 121.2(5) yes C59 . C64 . H641 . 119.4 no C63 . C64 . H641 . 119.3 no C58 . C65 . H651 . 109.3 no C58 . C65 . H652 . 109.0 no H651 . C65 . H652 . 109.0 no C58 . C65 . H653 . 109.6 no H651 . C65 . H653 . 110.2 no H652 . C65 . H653 . 109.8 no N57 . C66 . C67 . 113.9(4) yes N57 . C66 . H661 . 108.2 no C67 . C66 . H661 . 107.9 no N57 . C66 . H662 . 107.8 no C67 . C66 . H662 . 109.6 no H661 . C66 . H662 . 109.4 no C66 . C67 . C68 . 121.4(5) yes C66 . C67 . C72 . 119.4(5) yes C68 . C67 . C72 . 119.2(5) yes C67 . C68 . C69 . 118.8(5) yes C67 . C68 . H681 . 120.3 no C69 . C68 . H681 . 120.9 no C68 . C69 . C70 . 121.4(6) yes C68 . C69 . H691 . 118.6 no C70 . C69 . H691 . 120.0 no C69 . C70 . C71 . 120.1(6) yes C69 . C70 . H701 . 120.1 no C71 . C70 . H701 . 119.8 no C70 . C71 . C72 . 118.2(6) yes C70 . C71 . H711 . 120.8 no C72 . C71 . H711 . 120.9 no C71 . C72 . C67 . 122.3(6) yes C71 . C72 . H721 . 119.2 no C67 . C72 . H721 . 118.4 no C41 . C73 . C74 . 111.9(3) yes C41 . C73 . C81 . 117.4(4) yes C74 . C73 . C81 . 109.9(4) yes C41 . C73 . H731 . 105.2 no C74 . C73 . H731 . 104.9 no C81 . C73 . H731 . 106.4 no C73 . C74 . O75 . 111.1(3) yes C73 . C74 . O80 . 124.0(4) yes O75 . C74 . O80 . 124.8(4) yes C74 . O75 . C76 . 121.1(4) yes O75 . C76 . C77 . 101.1(4) yes O75 . C76 . C78 . 111.3(4) yes C77 . C76 . C78 . 110.4(6) yes O75 . C76 . C79 . 109.8(4) yes C77 . C76 . C79 . 111.5(6) yes C78 . C76 . C79 . 112.2(6) yes C76 . C77 . H771 . 107.3 no C76 . C77 . H772 . 108.0 no H771 . C77 . H772 . 111.5 no C76 . C77 . H773 . 108.3 no H771 . C77 . H773 . 110.6 no H772 . C77 . H773 . 110.9 no C76 . C78 . H781 . 109.4 no C76 . C78 . H782 . 107.1 no H781 . C78 . H782 . 110.4 no C76 . C78 . H783 . 107.5 no H781 . C78 . H783 . 111.1 no H782 . C78 . H783 . 111.3 no C76 . C79 . H791 . 110.3 no C76 . C79 . H792 . 109.1 no H791 . C79 . H792 . 109.5 no C76 . C79 . H793 . 106.5 no H791 . C79 . H793 . 110.6 no H792 . C79 . H793 . 110.8 no C73 . C81 . H811 . 108.7 no C73 . C81 . H812 . 110.3 no H811 . C81 . H812 . 109.6 no C73 . C81 . H813 . 108.3 no H811 . C81 . H813 . 110.2 no H812 . C81 . H813 . 109.8 no C5 . C82 . H821 . 113.7 no C5 . C82 . H822 . 105.1 no H821 . C82 . H822 . 110.2 no C5 . C82 . H823 . 111.1 no H821 . C82 . H823 . 108.5 no H822 . C82 . H823 . 108.0 no