# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2011 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Dr J Clayden' _publ_contact_author_email j.p.Clayden@man.ac.uk _publ_section_title ; A general synthetic approach to the amnesic shellfish toxins: total synthesis of (-)-isodomoic acid B, (-)-isodomoic acid E and (-)-isodomoic acid F ; loop_ _publ_author_name J.Clayden G.Lemiere S.Sedehizadeh J.Toueg N.Fleary-Roberts # Attachment '- s3176.cif' data_s3176 _database_code_depnum_ccdc_archive 'CCDC 785966' #TrackingRef '- s3176.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; #------------------------------------------------------------------------------ _publ_section_exptl_refinement ; The structure was solved by the direct methods and the asymmetric unit contains the molecule and 0.5 water molecule. All non-H atoms were refined anisotropically. H atoms bonded to C were included in calculated positions. One of those bonded to O1s was found by difference Fourier methods and refined with restraints on the bond length to O1s and isotropic thermal parameter contrained to be 1.5 times that of O1s; the other water H atom could not be located. ; _publ_section_comment ; ENTER TEXT ; _publ_section_references ; Bruker (2001). SMART (Version 5.625), SADABS (Version 2.03a) and SHELXTL (Version 6.12). Bruker AXS Inc., Madison, Wisconsin, USA. Bruker (2002). SAINT. Version 6.36a. Bruker AXS Inc., Madison, Wisconsin, USA. M. C. Burla, R. Caliandro, M. Camalli, B. Carrozzini, G. L. Cascarano, L. De Caro,C. Giacovazzo, G. Polidori and R. Spagna SIR2004: an improved tool for crystal structure determination and refinement J. Appl. Cryst. (2005). 38, 381-388 Sheldrick, G. M. (1997). SHELXS-97 and SHELXL-97. University of G\"ottingen, Germany. Sheldrick, G, M. (2005). CELL_NOW. University of G\"ottingen, Germany. Sheldrick, G, M. (2007). TWINABS. University of G\"ottingen, Germany. Spek, A.L. (2003) J.Appl.Cryst. 36, 2003, 7-13. ; _publ_section_acknowledgements ; ENTER ACKNOWLEDGEMENTS ; _publ_section_table_legends ; ENTER TABLE LEGENDS ; _publ_section_figure_captions ; ENTER FIGURE CAPTIONS ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C26 H33 N O2 Si, 0.5(H2 O)' _chemical_formula_sum 'C26 H34 N O2.50 Si' _chemical_formula_weight 428.63 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 _symmetry_space_group_name_Hall -P2ybc 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 11.549(3) _cell_length_b 15.630(4) _cell_length_c 13.138(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.792(5) _cell_angle_gamma 90.00 _cell_volume 2371.4(11) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 911 _cell_measurement_theta_min 2.19 _cell_measurement_theta_max 23.19 _exptl_crystal_description rod _exptl_crystal_colour colourless _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.201 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 924 _exptl_absorpt_coefficient_mu 0.123 _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 100(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 and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12245 _diffrn_reflns_av_R_equivalents 0.0693 _diffrn_reflns_av_sigmaI/netI 0.0925 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.76 _diffrn_reflns_theta_max 25.03 _reflns_number_total 4186 _reflns_number_gt 2786 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _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^)+(0.0422P)^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_number_reflns 4186 _refine_ls_number_parameters 288 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0847 _refine_ls_R_factor_gt 0.0491 _refine_ls_wR_factor_ref 0.1058 _refine_ls_wR_factor_gt 0.0959 _refine_ls_goodness_of_fit_ref 0.897 _refine_ls_restrained_S_all 0.897 _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 1.04174(6) 0.68110(4) 0.18449(5) 0.01994(19) Uani 1 1 d . . . O1 O 0.74892(13) 0.78841(9) 0.24616(12) 0.0208(4) Uani 1 1 d . . . O2 O 0.74047(17) 0.50352(10) -0.00883(16) 0.0440(6) Uani 1 1 d . . . N1 N 0.66024(15) 0.82155(11) 0.09339(14) 0.0142(4) Uani 1 1 d . . . C1 C 0.74659(19) 0.78728(13) 0.15265(18) 0.0148(5) Uani 1 1 d . . . C2 C 0.83666(19) 0.74774(14) 0.08315(17) 0.0154(5) Uani 1 1 d . . . H2 H 0.8994 0.7908 0.0728 0.018 Uiso 1 1 calc R . . C3 C 0.8932(2) 0.66449(13) 0.12566(18) 0.0167(6) Uani 1 1 d . . . H3 H 0.8420 0.6429 0.1808 0.020 Uiso 1 1 calc R . . C4 C 0.8965(2) 0.59460(14) 0.04286(19) 0.0233(6) Uani 1 1 d . . . H4A H 0.9467 0.6137 -0.0132 0.028 Uiso 1 1 calc R . . H4B H 0.9303 0.5417 0.0721 0.028 Uiso 1 1 calc R . . C5 C 0.7776(2) 0.57582(15) 0.00138(18) 0.0235(6) Uani 1 1 d . . . C6 C 0.7040(2) 0.65273(13) -0.02127(18) 0.0191(6) Uani 1 1 d . . . H6A H 0.6403 0.6548 0.0283 0.023 Uiso 1 1 calc R . . H6B H 0.6687 0.6459 -0.0899 0.023 Uiso 1 1 calc R . . C7 C 0.76933(19) 0.73797(13) -0.01748(18) 0.0146(5) Uani 1 1 d . . . H7 H 0.8227 0.7429 -0.0765 0.018 Uiso 1 1 calc R . . C8 C 0.6840(2) 0.81401(14) -0.01589(17) 0.0159(5) Uani 1 1 d . . . H8 H 0.6110 0.7970 -0.0524 0.019 Uiso 1 1 calc R . . C9 C 0.56143(19) 0.87037(14) 0.13694(17) 0.0152(5) Uani 1 1 d . . . C10 C 0.49582(19) 0.81415(15) 0.21305(18) 0.0182(5) Uani 1 1 d . . . C11 C 0.4657(2) 0.73109(15) 0.1854(2) 0.0242(6) Uani 1 1 d . . . H11 H 0.4939 0.7079 0.1237 0.029 Uiso 1 1 calc R . . C12 C 0.3956(2) 0.68176(17) 0.2464(2) 0.0325(7) Uani 1 1 d . . . H12 H 0.3760 0.6252 0.2262 0.039 Uiso 1 1 calc R . . C13 C 0.3537(2) 0.71436(19) 0.3367(2) 0.0367(8) Uani 1 1 d . . . H13 H 0.3048 0.6807 0.3783 0.044 Uiso 1 1 calc R . . C14 C 0.3839(2) 0.79663(19) 0.3655(2) 0.0357(7) Uani 1 1 d . . . H14 H 0.3564 0.8195 0.4276 0.043 Uiso 1 1 calc R . . C15 C 0.4544(2) 0.84591(17) 0.30389(19) 0.0258(6) Uani 1 1 d . . . H15 H 0.4746 0.9023 0.3244 0.031 Uiso 1 1 calc R . . C16 C 0.6064(2) 0.95402(14) 0.18349(19) 0.0225(6) Uani 1 1 d . . . H16A H 0.6619 0.9411 0.2384 0.034 Uiso 1 1 calc R . . H16B H 0.5414 0.9866 0.2109 0.034 Uiso 1 1 calc R . . H16C H 0.6447 0.9879 0.1309 0.034 Uiso 1 1 calc R . . C17 C 0.4745(2) 0.89137(14) 0.05093(17) 0.0193(6) Uani 1 1 d . . . H17A H 0.5140 0.9230 -0.0029 0.029 Uiso 1 1 calc R . . H17B H 0.4116 0.9264 0.0779 0.029 Uiso 1 1 calc R . . H17C H 0.4426 0.8381 0.0229 0.029 Uiso 1 1 calc R . . C18 C 1.0333(2) 0.76217(15) 0.28836(19) 0.0269(6) Uani 1 1 d . . . H18A H 0.9922 0.7377 0.3463 0.040 Uiso 1 1 calc R . . H18B H 0.9916 0.8127 0.2634 0.040 Uiso 1 1 calc R . . H18C H 1.1118 0.7786 0.3100 0.040 Uiso 1 1 calc R . . C19 C 1.0922(2) 0.57704(15) 0.2395(2) 0.0334(7) Uani 1 1 d . . . H19A H 1.1626 0.5865 0.2805 0.050 Uiso 1 1 calc R . . H19B H 1.1090 0.5370 0.1842 0.050 Uiso 1 1 calc R . . H19C H 1.0316 0.5531 0.2825 0.050 Uiso 1 1 calc R . . C20 C 1.1405(2) 0.71682(15) 0.08182(19) 0.0256(6) Uani 1 1 d . . . H20A H 1.2148 0.7345 0.1120 0.038 Uiso 1 1 calc R . . H20B H 1.1056 0.7652 0.0453 0.038 Uiso 1 1 calc R . . H20C H 1.1531 0.6695 0.0343 0.038 Uiso 1 1 calc R . . C21 C 0.7311(2) 0.89514(14) -0.06468(18) 0.0176(6) Uani 1 1 d . . . C22 C 0.8077(2) 0.94980(15) -0.0131(2) 0.0234(6) Uani 1 1 d . . . H22 H 0.8310 0.9372 0.0549 0.028 Uiso 1 1 calc R . . C23 C 0.8499(2) 1.02266(15) -0.0610(2) 0.0306(7) Uani 1 1 d . . . H23 H 0.9019 1.0596 -0.0255 0.037 Uiso 1 1 calc R . . C24 C 0.8167(2) 1.04152(16) -0.1597(2) 0.0326(7) Uani 1 1 d . . . H24 H 0.8456 1.0914 -0.1919 0.039 Uiso 1 1 calc R . . C25 C 0.7416(2) 0.98799(15) -0.2117(2) 0.0304(7) Uani 1 1 d . . . H25 H 0.7189 1.0007 -0.2798 0.036 Uiso 1 1 calc R . . C26 C 0.6989(2) 0.91497(14) -0.16375(19) 0.0215(6) Uani 1 1 d . . . H26 H 0.6469 0.8784 -0.1997 0.026 Uiso 1 1 calc R . . O1S O 0.5066(5) 0.4662(3) -0.0679(4) 0.0753(16) Uani 0.50 1 d PD . . H1O H 0.565(5) 0.490(5) -0.038(6) 0.113 Uiso 0.50 1 d PD . . 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 0.0140(4) 0.0236(4) 0.0222(4) 0.0048(3) 0.0021(3) 0.0029(3) O1 0.0188(9) 0.0259(10) 0.0177(10) -0.0007(7) 0.0016(8) 0.0042(7) O2 0.0479(13) 0.0168(10) 0.0668(16) -0.0046(9) -0.0146(11) -0.0037(9) N1 0.0115(10) 0.0160(10) 0.0150(11) 0.0008(9) 0.0018(8) 0.0034(9) C1 0.0155(13) 0.0134(12) 0.0155(14) -0.0005(10) 0.0031(11) -0.0021(10) C2 0.0102(12) 0.0175(13) 0.0185(14) 0.0000(10) 0.0007(11) -0.0009(10) C3 0.0161(13) 0.0167(13) 0.0175(13) 0.0039(10) 0.0053(11) 0.0017(10) C4 0.0238(15) 0.0199(13) 0.0263(15) 0.0004(11) 0.0016(12) 0.0039(11) C5 0.0312(16) 0.0189(14) 0.0206(15) -0.0034(11) 0.0037(12) 0.0015(12) C6 0.0181(13) 0.0214(13) 0.0178(14) -0.0021(10) 0.0008(11) -0.0028(11) C7 0.0123(12) 0.0163(12) 0.0154(13) -0.0006(10) 0.0019(10) -0.0002(10) C8 0.0139(13) 0.0178(12) 0.0158(13) 0.0005(10) -0.0009(10) -0.0001(11) C9 0.0133(12) 0.0165(12) 0.0159(14) -0.0017(10) 0.0035(10) 0.0040(10) C10 0.0088(12) 0.0246(13) 0.0211(14) 0.0049(11) -0.0020(10) 0.0048(11) C11 0.0147(13) 0.0255(14) 0.0325(17) 0.0090(12) 0.0042(12) 0.0049(11) C12 0.0170(14) 0.0331(16) 0.047(2) 0.0198(15) -0.0002(14) 0.0028(13) C13 0.0124(14) 0.061(2) 0.0372(19) 0.0282(16) -0.0008(13) -0.0024(14) C14 0.0168(15) 0.070(2) 0.0205(16) 0.0109(15) 0.0009(12) 0.0057(15) C15 0.0154(14) 0.0395(16) 0.0224(16) 0.0043(13) -0.0005(12) 0.0057(12) C16 0.0205(14) 0.0207(13) 0.0264(15) -0.0031(11) 0.0026(12) 0.0034(11) C17 0.0168(13) 0.0214(13) 0.0199(14) 0.0021(11) 0.0022(11) 0.0038(11) C18 0.0140(14) 0.0403(16) 0.0264(16) 0.0012(13) -0.0003(12) -0.0034(12) C19 0.0192(15) 0.0378(16) 0.0431(19) 0.0144(14) -0.0025(14) 0.0008(13) C20 0.0163(14) 0.0325(15) 0.0282(16) -0.0015(12) 0.0018(12) 0.0017(12) C21 0.0162(13) 0.0175(13) 0.0192(14) 0.0021(10) 0.0060(11) 0.0064(11) C22 0.0176(14) 0.0245(14) 0.0280(16) 0.0042(12) 0.0008(12) 0.0015(12) C23 0.0224(15) 0.0212(15) 0.049(2) 0.0034(13) 0.0064(14) -0.0011(12) C24 0.0332(17) 0.0208(14) 0.044(2) 0.0099(14) 0.0193(15) 0.0053(13) C25 0.0389(17) 0.0288(15) 0.0239(16) 0.0082(13) 0.0155(13) 0.0174(14) C26 0.0237(15) 0.0192(13) 0.0219(15) 0.0005(11) 0.0071(12) 0.0085(11) O1S 0.073(4) 0.078(3) 0.074(4) 0.000(3) -0.007(3) -0.028(3) _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 C20 1.864(3) . ? Si1 C18 1.866(3) . ? Si1 C19 1.870(2) . ? Si1 C3 1.890(2) . ? O1 C1 1.229(3) . ? O2 C5 1.215(3) . ? N1 C1 1.366(3) . ? N1 C8 1.470(3) . ? N1 C9 1.493(3) . ? C1 C2 1.525(3) . ? C2 C7 1.532(3) . ? C2 C3 1.556(3) . ? C2 H2 1.0000 . ? C3 C4 1.542(3) . ? C3 H3 1.0000 . ? C4 C5 1.499(3) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 C6 1.499(3) . ? C6 C7 1.532(3) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 C8 1.544(3) . ? C7 H7 1.0000 . ? C8 C21 1.525(3) . ? C8 H8 1.0000 . ? C9 C16 1.531(3) . ? C9 C17 1.536(3) . ? C9 C10 1.539(3) . ? C10 C15 1.384(3) . ? C10 C11 1.391(3) . ? C11 C12 1.382(3) . ? C11 H11 0.9500 . ? C12 C13 1.385(4) . ? C12 H12 0.9500 . ? C13 C14 1.384(4) . ? C13 H13 0.9500 . ? C14 C15 1.389(4) . ? C14 H14 0.9500 . ? C15 H15 0.9500 . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? C21 C26 1.384(3) . ? C21 C22 1.398(3) . ? C22 C23 1.393(3) . ? C22 H22 0.9500 . ? C23 C24 1.379(4) . ? C23 H23 0.9500 . ? C24 C25 1.380(4) . ? C24 H24 0.9500 . ? C25 C26 1.397(3) . ? C25 H25 0.9500 . ? C26 H26 0.9500 . ? O1S H1O 0.86(2) . ? 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 C20 Si1 C18 111.37(12) . . ? C20 Si1 C19 110.45(12) . . ? C18 Si1 C19 109.10(12) . . ? C20 Si1 C3 107.85(11) . . ? C18 Si1 C3 109.66(11) . . ? C19 Si1 C3 108.36(11) . . ? C1 N1 C8 112.36(18) . . ? C1 N1 C9 122.53(18) . . ? C8 N1 C9 124.69(17) . . ? O1 C1 N1 124.7(2) . . ? O1 C1 C2 126.8(2) . . ? N1 C1 C2 108.45(19) . . ? C1 C2 C7 102.41(18) . . ? C1 C2 C3 114.2(2) . . ? C7 C2 C3 115.58(18) . . ? C1 C2 H2 108.1 . . ? C7 C2 H2 108.1 . . ? C3 C2 H2 108.1 . . ? C4 C3 C2 110.69(19) . . ? C4 C3 Si1 110.79(16) . . ? C2 C3 Si1 113.95(15) . . ? C4 C3 H3 107.0 . . ? C2 C3 H3 107.0 . . ? Si1 C3 H3 107.0 . . ? C5 C4 C3 111.3(2) . . ? C5 C4 H4A 109.4 . . ? C3 C4 H4A 109.4 . . ? C5 C4 H4B 109.4 . . ? C3 C4 H4B 109.4 . . ? H4A C4 H4B 108.0 . . ? O2 C5 C4 122.8(2) . . ? O2 C5 C6 121.7(2) . . ? C4 C5 C6 115.4(2) . . ? C5 C6 C7 114.43(19) . . ? C5 C6 H6A 108.7 . . ? C7 C6 H6A 108.7 . . ? C5 C6 H6B 108.7 . . ? C7 C6 H6B 108.7 . . ? H6A C6 H6B 107.6 . . ? C2 C7 C6 111.01(18) . . ? C2 C7 C8 103.17(17) . . ? C6 C7 C8 110.85(18) . . ? C2 C7 H7 110.5 . . ? C6 C7 H7 110.5 . . ? C8 C7 H7 110.5 . . ? N1 C8 C21 114.61(18) . . ? N1 C8 C7 101.70(17) . . ? C21 C8 C7 113.76(19) . . ? N1 C8 H8 108.8 . . ? C21 C8 H8 108.8 . . ? C7 C8 H8 108.8 . . ? N1 C9 C16 109.42(18) . . ? N1 C9 C17 108.80(18) . . ? C16 C9 C17 109.02(18) . . ? N1 C9 C10 110.06(17) . . ? C16 C9 C10 113.3(2) . . ? C17 C9 C10 106.11(18) . . ? C15 C10 C11 118.2(2) . . ? C15 C10 C9 122.3(2) . . ? C11 C10 C9 119.1(2) . . ? C12 C11 C10 121.1(3) . . ? C12 C11 H11 119.5 . . ? C10 C11 H11 119.5 . . ? C11 C12 C13 120.4(3) . . ? C11 C12 H12 119.8 . . ? C13 C12 H12 119.8 . . ? C14 C13 C12 119.1(3) . . ? C14 C13 H13 120.5 . . ? C12 C13 H13 120.5 . . ? C13 C14 C15 120.3(3) . . ? C13 C14 H14 119.9 . . ? C15 C14 H14 119.9 . . ? C10 C15 C14 121.0(3) . . ? C10 C15 H15 119.5 . . ? C14 C15 H15 119.5 . . ? C9 C16 H16A 109.5 . . ? C9 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C9 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C9 C17 H17A 109.5 . . ? C9 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C9 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? Si1 C18 H18A 109.5 . . ? Si1 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? Si1 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? Si1 C19 H19A 109.5 . . ? Si1 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? Si1 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? Si1 C20 H20A 109.5 . . ? Si1 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? Si1 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C26 C21 C22 118.7(2) . . ? C26 C21 C8 119.2(2) . . ? C22 C21 C8 122.1(2) . . ? C23 C22 C21 120.2(2) . . ? C23 C22 H22 119.9 . . ? C21 C22 H22 119.9 . . ? C24 C23 C22 120.4(3) . . ? C24 C23 H23 119.8 . . ? C22 C23 H23 119.8 . . ? C25 C24 C23 120.1(2) . . ? C25 C24 H24 120.0 . . ? C23 C24 H24 120.0 . . ? C24 C25 C26 119.7(3) . . ? C24 C25 H25 120.1 . . ? C26 C25 H25 120.1 . . ? C21 C26 C25 121.0(2) . . ? C21 C26 H26 119.5 . . ? C25 C26 H26 119.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C8 N1 C1 O1 177.3(2) . . . . ? C9 N1 C1 O1 4.4(3) . . . . ? C8 N1 C1 C2 -3.2(2) . . . . ? C9 N1 C1 C2 -176.04(18) . . . . ? O1 C1 C2 C7 161.0(2) . . . . ? N1 C1 C2 C7 -18.5(2) . . . . ? O1 C1 C2 C3 35.3(3) . . . . ? N1 C1 C2 C3 -144.24(18) . . . . ? C1 C2 C3 C4 133.6(2) . . . . ? C7 C2 C3 C4 15.1(3) . . . . ? C1 C2 C3 Si1 -100.8(2) . . . . ? C7 C2 C3 Si1 140.75(17) . . . . ? C20 Si1 C3 C4 61.24(18) . . . . ? C18 Si1 C3 C4 -177.32(16) . . . . ? C19 Si1 C3 C4 -58.3(2) . . . . ? C20 Si1 C3 C2 -64.36(19) . . . . ? C18 Si1 C3 C2 57.1(2) . . . . ? C19 Si1 C3 C2 176.07(17) . . . . ? C2 C3 C4 C5 -57.1(3) . . . . ? Si1 C3 C4 C5 175.46(16) . . . . ? C3 C4 C5 O2 -132.3(3) . . . . ? C3 C4 C5 C6 44.2(3) . . . . ? O2 C5 C6 C7 -172.5(2) . . . . ? C4 C5 C6 C7 10.9(3) . . . . ? C1 C2 C7 C6 -87.2(2) . . . . ? C3 C2 C7 C6 37.7(3) . . . . ? C1 C2 C7 C8 31.6(2) . . . . ? C3 C2 C7 C8 156.44(19) . . . . ? C5 C6 C7 C2 -52.4(3) . . . . ? C5 C6 C7 C8 -166.41(19) . . . . ? C1 N1 C8 C21 -99.9(2) . . . . ? C9 N1 C8 C21 72.7(3) . . . . ? C1 N1 C8 C7 23.2(2) . . . . ? C9 N1 C8 C7 -164.07(18) . . . . ? C2 C7 C8 N1 -33.2(2) . . . . ? C6 C7 C8 N1 85.7(2) . . . . ? C2 C7 C8 C21 90.5(2) . . . . ? C6 C7 C8 C21 -150.57(19) . . . . ? C1 N1 C9 C16 66.8(3) . . . . ? C8 N1 C9 C16 -105.1(2) . . . . ? C1 N1 C9 C17 -174.14(19) . . . . ? C8 N1 C9 C17 13.9(3) . . . . ? C1 N1 C9 C10 -58.3(3) . . . . ? C8 N1 C9 C10 129.8(2) . . . . ? N1 C9 C10 C15 139.7(2) . . . . ? C16 C9 C10 C15 16.8(3) . . . . ? C17 C9 C10 C15 -102.8(2) . . . . ? N1 C9 C10 C11 -47.5(3) . . . . ? C16 C9 C10 C11 -170.3(2) . . . . ? C17 C9 C10 C11 70.1(2) . . . . ? C15 C10 C11 C12 0.6(3) . . . . ? C9 C10 C11 C12 -172.5(2) . . . . ? C10 C11 C12 C13 0.0(4) . . . . ? C11 C12 C13 C14 -0.6(4) . . . . ? C12 C13 C14 C15 0.6(4) . . . . ? C11 C10 C15 C14 -0.6(3) . . . . ? C9 C10 C15 C14 172.3(2) . . . . ? C13 C14 C15 C10 0.0(4) . . . . ? N1 C8 C21 C26 -144.5(2) . . . . ? C7 C8 C21 C26 99.1(2) . . . . ? N1 C8 C21 C22 36.6(3) . . . . ? C7 C8 C21 C22 -79.9(3) . . . . ? C26 C21 C22 C23 0.1(3) . . . . ? C8 C21 C22 C23 179.1(2) . . . . ? C21 C22 C23 C24 0.0(4) . . . . ? C22 C23 C24 C25 -0.2(4) . . . . ? C23 C24 C25 C26 0.3(4) . . . . ? C22 C21 C26 C25 0.0(3) . . . . ? C8 C21 C26 C25 -179.0(2) . . . . ? C24 C25 C26 C21 -0.2(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 O1S H1O O2 0.86(2) 2.07(4) 2.860(5) 153(8) . _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.03 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.446 _refine_diff_density_min -0.398 _refine_diff_density_rms 0.052