# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2012 # Attachment '- Compound_34.cif' data_publication_text _journal_name_full Org.Biomol.Chem. _journal_coden_cambridge 0177 #TrackingRef '- Compound_34.cif' _publ_contact_author_name 'Andrew G H Wee' _publ_contact_author_address ;Department of Chemistry and Biochemistry University of Regina Regina Saskatchewan Canada S4S 0A2 ; _publ_contact_author_email andrew.wee@uregina.ca _publ_contact_author_phone +1(306)5854767 _publ_contact_author_fax +1(306)3372409 loop_ _publ_author_name _publ_author_address A.G.Wee ;Department of Chemistry and Biochemistry University of Regina Regina Saskatchewan Canada S4S 0A2 ; B.Zhang ;Department of Chemistry and Biochemistry University of Regina Regina Saskatchewan Canada S4S 0A2 ; # Attachment 'Cmpd12d.cif' data_384p21c _database_code_depnum_ccdc_archive 'CCDC 691157' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C24 H32 N2 O3 S Si2' _chemical_formula_sum 'C24 H32 N2 O3 S Si2' _chemical_formula_weight 484.76 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' S S 0.1246 0.1234 '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 P21/c _symmetry_space_group_name_Hall '-P 2ybc' 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 16.8073(4) _cell_length_b 9.1044(2) _cell_length_c 23.0328(5) _cell_angle_alpha 90.00 _cell_angle_beta 131.7160(10) _cell_angle_gamma 90.00 _cell_volume 2630.86(10) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 41055 _cell_measurement_theta_min 0.998 _cell_measurement_theta_max 27.485 _exptl_crystal_description chip _exptl_crystal_colour colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.224 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1032 _exptl_absorpt_coefficient_mu 0.241 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_correction_T_min 0.917 _exptl_absorpt_correction_T_max 0.976 _exptl_absorpt_process_details 'Shelxtl 6.10 (Bruker-AXS, 2000)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_measurement_device 'Nonius KappaCCD' _diffrn_measurement_method '\f scans and \w scans with \k offsets' _diffrn_detector_area_resol_mean 9 _diffrn_radiation_monochromator 'horizonally mounted graphite crystal' _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 40367 _diffrn_reflns_av_R_equivalents 0.0543 _diffrn_reflns_av_sigmaI/netI 0.0280 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 2.37 _diffrn_reflns_theta_max 25.68 _reflns_number_total 4992 _reflns_number_gt 4064 _reflns_threshold_expression >2\s(I) _computing_data_collection 'Collect (Nonius BV, 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_structure_solution 'SIR97 (Altomare et al., 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0415P)^2^+1.2851P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4992 _refine_ls_number_parameters 326 _refine_ls_number_restraints 170 _refine_ls_R_factor_all 0.0543 _refine_ls_R_factor_gt 0.0403 _refine_ls_wR_factor_ref 0.1019 _refine_ls_wR_factor_gt 0.0938 _refine_ls_goodness_of_fit_ref 1.053 _refine_ls_restrained_S_all 1.046 _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 S1 S 0.33054(4) 0.22235(5) -0.04369(3) 0.03899(14) Uani 1 1 d D . . Si1 Si 0.80713(5) 0.29191(7) 0.20223(3) 0.04617(16) Uani 1 1 d . . . Si2 Si 0.81825(5) 0.53674(6) 0.31155(3) 0.04534(16) Uani 1 1 d . . . O1 O 0.66096(11) 0.28543(14) 0.27371(7) 0.0410(3) Uani 1 1 d . . . O2 O 0.22237(12) 0.2153(2) -0.11485(9) 0.0628(5) Uani 1 1 d . A . O3 O 0.41445(11) 0.22854(15) -0.04460(8) 0.0437(3) Uani 1 1 d . A . N1 N 0.62993(11) 0.40825(16) 0.17357(8) 0.0315(3) Uani 1 1 d . . . N2 N 0.34173(11) 0.37448(17) 0.00181(8) 0.0336(3) Uani 1 1 d . A . C1 C 0.59965(14) 0.33531(19) 0.20704(10) 0.0329(4) Uani 1 1 d . . . C2 C 0.48101(14) 0.32724(19) 0.15153(10) 0.0319(4) Uani 1 1 d . A . H2 H 0.4442 0.2364 0.1475 0.038 Uiso 1 1 calc R . . C3 C 0.44513(13) 0.40420(18) 0.07931(10) 0.0300(4) Uani 1 1 d . . . C4 C 0.54219(13) 0.4480(2) 0.09177(10) 0.0340(4) Uani 1 1 d . A . H4A H 0.5464 0.3928 0.0569 0.041 Uiso 1 1 calc R . . H4B H 0.5422 0.5546 0.0833 0.041 Uiso 1 1 calc R . . C5 C 0.42590(14) 0.47591(19) 0.12745(10) 0.0339(4) Uani 1 1 d . A . H5 H 0.4674 0.5653 0.1587 0.041 Uiso 1 1 calc R . . C6 C 0.30814(14) 0.4750(2) 0.07656(11) 0.0376(4) Uani 1 1 d . . . C7 C 0.24566(16) 0.5336(2) 0.09011(14) 0.0501(5) Uani 1 1 d . A . H7 H 0.2773 0.5769 0.1388 0.060 Uiso 1 1 calc R . . C8 C 0.13545(18) 0.5274(3) 0.03061(16) 0.0645(7) Uani 1 1 d . . . H8 H 0.0911 0.5664 0.0388 0.077 Uiso 1 1 calc R A . C9 C 0.08987(17) 0.4652(3) -0.04015(15) 0.0647(7) Uani 1 1 d . A . H9 H 0.0144 0.4616 -0.0798 0.078 Uiso 1 1 calc R . . C10 C 0.15117(16) 0.4078(3) -0.05503(13) 0.0535(6) Uani 1 1 d . . . H10 H 0.1193 0.3664 -0.1041 0.064 Uiso 1 1 calc R A . C11 C 0.26117(15) 0.4135(2) 0.00488(12) 0.0394(4) Uani 1 1 d . A . C12 C 0.74136(13) 0.4466(2) 0.21240(10) 0.0346(4) Uani 1 1 d . . . H12 H 0.7335 0.5269 0.1793 0.042 Uiso 1 1 calc R . . C13 C 0.7327(2) 0.2606(3) 0.09731(14) 0.0614(6) Uani 1 1 d . . . H13A H 0.7712 0.1892 0.0921 0.092 Uiso 1 1 calc R . . H13B H 0.7262 0.3535 0.0730 0.092 Uiso 1 1 calc R . . H13C H 0.6615 0.2226 0.0716 0.092 Uiso 1 1 calc R . . C14 C 0.8065(2) 0.1181(3) 0.24437(16) 0.0702(7) Uani 1 1 d . . . H14A H 0.8389 0.0396 0.2370 0.105 Uiso 1 1 calc R . . H14B H 0.7329 0.0915 0.2183 0.105 Uiso 1 1 calc R . . H14C H 0.8474 0.1317 0.3001 0.105 Uiso 1 1 calc R . . C15 C 0.94573(19) 0.3482(4) 0.25065(17) 0.0807(9) Uani 1 1 d . . . H15A H 0.9792 0.2715 0.2433 0.121 Uiso 1 1 calc R . . H15B H 0.9870 0.3625 0.3064 0.121 Uiso 1 1 calc R . . H15C H 0.9438 0.4403 0.2277 0.121 Uiso 1 1 calc R . . C16 C 0.89855(19) 0.4058(3) 0.39498(12) 0.0627(7) Uani 1 1 d . . . H16A H 0.9275 0.4571 0.4430 0.094 Uiso 1 1 calc R . . H16B H 0.9573 0.3670 0.4000 0.094 Uiso 1 1 calc R . . H16C H 0.8530 0.3246 0.3858 0.094 Uiso 1 1 calc R . . C17 C 0.9125(2) 0.6711(3) 0.32320(16) 0.0751(8) Uani 1 1 d . . . H17A H 0.9495 0.7263 0.3716 0.113 Uiso 1 1 calc R . . H17B H 0.8725 0.7392 0.2791 0.113 Uiso 1 1 calc R . . H17C H 0.9648 0.6180 0.3250 0.113 Uiso 1 1 calc R . . C18 C 0.7228(2) 0.6440(3) 0.31083(14) 0.0606(6) Uani 1 1 d . . . H18A H 0.7621 0.6957 0.3605 0.091 Uiso 1 1 calc R . . H18B H 0.6710 0.5770 0.3034 0.091 Uiso 1 1 calc R . . H18C H 0.6853 0.7155 0.2683 0.091 Uiso 1 1 calc R . . C19B C 0.3676(11) 0.0809(10) 0.0221(7) 0.036(2) Uani 1 1 d . . . C20B C 0.2961(12) 0.0328(9) 0.0286(8) 0.062(2) Uani 1 1 d . . . H20B H 0.2248 0.0681 -0.0062 0.074 Uiso 1 1 calc R . . C21B C 0.3280(15) -0.0666(9) 0.0859(8) 0.071(3) Uani 1 1 d . . . H21B H 0.2788 -0.0997 0.0904 0.085 Uiso 1 1 calc R . . C22B C 0.4315(16) -0.1179(10) 0.1366(7) 0.075(3) Uani 1 1 d . . . H22B H 0.4535 -0.1863 0.1760 0.089 Uiso 1 1 calc R . . C23B C 0.5031(14) -0.0697(11) 0.1300(7) 0.063(2) Uani 1 1 d . . . H23B H 0.5743 -0.1050 0.1649 0.075 Uiso 1 1 calc R . . C24B C 0.4711(12) 0.0296(12) 0.0727(7) 0.042(2) Uani 1 1 d . . . H24B H 0.5204 0.0628 0.0682 0.050 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 S1 0.0436(3) 0.0418(3) 0.0356(3) -0.0081(2) 0.0280(2) -0.0078(2) Si1 0.0406(3) 0.0502(3) 0.0444(3) -0.0010(3) 0.0269(3) 0.0072(3) Si2 0.0460(3) 0.0415(3) 0.0341(3) -0.0062(2) 0.0206(3) -0.0067(2) O1 0.0492(8) 0.0413(7) 0.0293(7) 0.0085(6) 0.0247(6) 0.0080(6) O2 0.0443(8) 0.0827(12) 0.0423(8) -0.0274(8) 0.0208(7) -0.0112(8) O3 0.0552(8) 0.0452(8) 0.0476(8) -0.0003(6) 0.0412(7) -0.0038(6) N1 0.0307(7) 0.0334(8) 0.0252(7) 0.0046(6) 0.0164(6) 0.0019(6) N2 0.0305(7) 0.0341(8) 0.0301(8) -0.0029(6) 0.0176(7) -0.0024(6) C1 0.0421(10) 0.0267(8) 0.0305(9) 0.0014(7) 0.0244(8) 0.0038(7) C2 0.0398(9) 0.0278(9) 0.0327(9) 0.0008(7) 0.0259(8) 0.0001(7) C3 0.0313(9) 0.0284(9) 0.0269(9) 0.0013(7) 0.0179(8) -0.0010(7) C4 0.0308(9) 0.0377(10) 0.0276(9) 0.0072(7) 0.0169(8) 0.0006(7) C5 0.0344(9) 0.0277(9) 0.0357(10) -0.0035(7) 0.0217(8) -0.0015(7) C6 0.0369(10) 0.0282(9) 0.0455(11) -0.0076(8) 0.0265(9) -0.0041(8) C7 0.0453(11) 0.0440(12) 0.0625(14) -0.0186(10) 0.0366(11) -0.0064(9) C8 0.0445(12) 0.0653(16) 0.0844(18) -0.0285(14) 0.0432(13) -0.0093(11) C9 0.0342(11) 0.0694(16) 0.0741(17) -0.0239(13) 0.0291(12) -0.0083(11) C10 0.0365(11) 0.0595(14) 0.0514(13) -0.0164(11) 0.0238(10) -0.0067(10) C11 0.0356(10) 0.0346(10) 0.0442(11) -0.0062(8) 0.0250(9) -0.0029(8) C12 0.0306(9) 0.0365(10) 0.0313(9) 0.0016(7) 0.0184(8) -0.0002(7) C13 0.0703(16) 0.0610(15) 0.0604(15) -0.0115(12) 0.0466(14) -0.0002(12) C14 0.0846(18) 0.0520(14) 0.0759(17) 0.0127(13) 0.0542(16) 0.0266(13) C15 0.0472(14) 0.107(2) 0.083(2) -0.0112(18) 0.0408(14) 0.0066(15) C16 0.0528(13) 0.0696(16) 0.0312(11) -0.0005(11) 0.0135(10) -0.0025(12) C17 0.0697(17) 0.0675(17) 0.0680(17) -0.0171(14) 0.0374(15) -0.0287(14) C18 0.0833(17) 0.0425(13) 0.0574(14) -0.0072(11) 0.0474(14) 0.0031(12) C19B 0.063(5) 0.021(3) 0.050(4) -0.017(2) 0.049(4) -0.021(3) C20B 0.080(5) 0.053(4) 0.086(5) -0.035(3) 0.069(5) -0.034(3) C21B 0.132(7) 0.044(4) 0.113(6) -0.032(4) 0.114(6) -0.046(4) C22B 0.157(9) 0.019(3) 0.122(6) -0.001(3) 0.124(6) -0.012(4) C23B 0.115(6) 0.027(3) 0.096(5) 0.010(3) 0.091(5) 0.010(4) C24B 0.071(5) 0.017(3) 0.068(4) 0.004(3) 0.060(4) 0.000(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 S1 O2 1.4248(15) . ? S1 O3 1.4255(14) . ? S1 N2 1.6702(16) . ? S1 C19B 1.756(2) . ? Si1 C14 1.860(3) . ? Si1 C13 1.861(2) . ? Si1 C15 1.864(3) . ? Si1 C12 1.8984(19) . ? Si2 C16 1.866(2) . ? Si2 C18 1.868(2) . ? Si2 C17 1.874(3) . ? Si2 C12 1.9057(19) . ? O1 C1 1.233(2) . ? N1 C1 1.348(2) . ? N1 C4 1.469(2) . ? N1 C12 1.483(2) . ? N2 C11 1.446(2) . ? N2 C3 1.467(2) . ? C1 C2 1.491(2) . ? C2 C3 1.512(2) . ? C2 C5 1.521(2) . ? C2 H2 1.0000 . ? C3 C5 1.496(3) . ? C3 C4 1.510(2) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 C6 1.484(2) . ? C5 H5 1.0000 . ? C6 C7 1.386(3) . ? C6 C11 1.388(3) . ? C7 C8 1.391(3) . ? C7 H7 0.9500 . ? C8 C9 1.379(3) . ? C8 H8 0.9500 . ? C9 C10 1.386(3) . ? C9 H9 0.9500 . ? C10 C11 1.389(3) . ? C10 H10 0.9500 . ? C12 H12 1.0000 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? 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 . ? C19B C20B 1.3799 . ? C19B C24B 1.3799 . ? C20B C21B 1.3800 . ? C20B H20B 0.9500 . ? C21B C22B 1.3799 . ? C21B H21B 0.9500 . ? C22B C23B 1.3799 . ? C22B H22B 0.9500 . ? C23B C24B 1.3800 . ? C23B H23B 0.9500 . ? C24B H24B 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 O2 S1 O3 120.17(10) . . ? O2 S1 N2 106.50(9) . . ? O3 S1 N2 106.08(8) . . ? O2 S1 C19B 114.1(5) . . ? O3 S1 C19B 104.8(4) . . ? N2 S1 C19B 103.9(4) . . ? C14 Si1 C13 108.37(13) . . ? C14 Si1 C15 111.14(14) . . ? C13 Si1 C15 108.13(13) . . ? C14 Si1 C12 111.15(11) . . ? C13 Si1 C12 109.29(10) . . ? C15 Si1 C12 108.70(11) . . ? C16 Si2 C18 111.79(12) . . ? C16 Si2 C17 107.83(12) . . ? C18 Si2 C17 107.40(13) . . ? C16 Si2 C12 114.07(10) . . ? C18 Si2 C12 108.72(10) . . ? C17 Si2 C12 106.69(11) . . ? C1 N1 C4 114.59(14) . . ? C1 N1 C12 125.24(15) . . ? C4 N1 C12 120.15(14) . . ? C11 N2 C3 106.54(14) . . ? C11 N2 S1 121.08(12) . . ? C3 N2 S1 117.66(12) . . ? O1 C1 N1 124.96(17) . . ? O1 C1 C2 125.61(17) . . ? N1 C1 C2 109.41(15) . . ? C1 C2 C3 104.32(14) . . ? C1 C2 C5 114.28(15) . . ? C3 C2 C5 59.09(12) . . ? C1 C2 H2 120.8 . . ? C3 C2 H2 120.8 . . ? C5 C2 H2 120.8 . . ? N2 C3 C5 108.50(14) . . ? N2 C3 C4 122.36(15) . . ? C5 C3 C4 118.87(15) . . ? N2 C3 C2 122.39(15) . . ? C5 C3 C2 60.76(12) . . ? C4 C3 C2 108.89(14) . . ? N1 C4 C3 102.36(14) . . ? N1 C4 H4A 111.3 . . ? C3 C4 H4A 111.3 . . ? N1 C4 H4B 111.3 . . ? C3 C4 H4B 111.3 . . ? H4A C4 H4B 109.2 . . ? C6 C5 C3 104.14(15) . . ? C6 C5 C2 116.82(15) . . ? C3 C5 C2 60.15(11) . . ? C6 C5 H5 119.9 . . ? C3 C5 H5 119.9 . . ? C2 C5 H5 119.9 . . ? C7 C6 C11 120.43(18) . . ? C7 C6 C5 129.18(18) . . ? C11 C6 C5 110.23(17) . . ? C6 C7 C8 118.3(2) . . ? C6 C7 H7 120.8 . . ? C8 C7 H7 120.8 . . ? C9 C8 C7 120.6(2) . . ? C9 C8 H8 119.7 . . ? C7 C8 H8 119.7 . . ? C8 C9 C10 121.8(2) . . ? C8 C9 H9 119.1 . . ? C10 C9 H9 119.1 . . ? C9 C10 C11 117.2(2) . . ? C9 C10 H10 121.4 . . ? C11 C10 H10 121.4 . . ? C6 C11 C10 121.60(19) . . ? C6 C11 N2 110.31(16) . . ? C10 C11 N2 127.79(19) . . ? N1 C12 Si1 110.87(12) . . ? N1 C12 Si2 113.64(13) . . ? Si1 C12 Si2 118.76(9) . . ? N1 C12 H12 103.9 . . ? Si1 C12 H12 103.9 . . ? Si2 C12 H12 103.9 . . ? Si1 C13 H13A 109.5 . . ? Si1 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? Si1 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? Si1 C14 H14A 109.5 . . ? Si1 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? Si1 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? Si1 C15 H15A 109.5 . . ? Si1 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? Si1 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? Si2 C16 H16A 109.5 . . ? Si2 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? Si2 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? Si2 C17 H17A 109.5 . . ? Si2 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? Si2 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? Si2 C18 H18A 109.5 . . ? Si2 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? Si2 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C20B C19B C24B 120.0 . . ? C20B C19B S1 119.5(5) . . ? C24B C19B S1 120.1(5) . . ? C19B C20B C21B 120.0 . . ? C19B C20B H20B 120.0 . . ? C21B C20B H20B 120.0 . . ? C22B C21B C20B 120.0 . . ? C22B C21B H21B 120.0 . . ? C20B C21B H21B 120.0 . . ? C21B C22B C23B 120.0 . . ? C21B C22B H22B 120.0 . . ? C23B C22B H22B 120.0 . . ? C22B C23B C24B 120.0 . . ? C22B C23B H23B 120.0 . . ? C24B C23B H23B 120.0 . . ? C19B C24B C23B 120.0 . . ? C19B C24B H24B 120.0 . . ? C23B C24B H24B 120.0 . . ? 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 O2 S1 N2 C11 43.19(17) . . . . ? O3 S1 N2 C11 172.30(14) . . . . ? C19A S1 N2 C11 -68.2(5) . . . . ? C19B S1 N2 C11 -77.6(5) . . . . ? O2 S1 N2 C3 176.91(14) . . . . ? O3 S1 N2 C3 -53.98(15) . . . . ? C19B S1 N2 C3 56.2(5) . . . . ? C4 N1 C1 O1 176.08(17) . . . . ? C12 N1 C1 O1 -3.0(3) . . . . ? C4 N1 C1 C2 -5.0(2) . . . . ? C12 N1 C1 C2 175.94(15) . . . . ? O1 C1 C2 C3 179.83(17) . . . . ? N1 C1 C2 C3 0.94(19) . . . . ? O1 C1 C2 C5 117.6(2) . . . . ? N1 C1 C2 C5 -61.3(2) . . . . ? C11 N2 C3 C5 -5.47(18) . . . . ? S1 N2 C3 C5 -145.25(13) . . . . ? C11 N2 C3 C4 -150.04(16) . . . . ? S1 N2 C3 C4 70.18(19) . . . . ? C11 N2 C3 C2 61.1(2) . . . . ? S1 N2 C3 C2 -78.68(19) . . . . ? C1 C2 C3 N2 155.68(15) . . . . ? C5 C2 C3 N2 -94.33(18) . . . . ? C1 C2 C3 C5 -109.98(15) . . . . ? C1 C2 C3 C4 3.18(19) . . . . ? C5 C2 C3 C4 113.16(16) . . . . ? C1 N1 C4 C3 6.7(2) . . . . ? C12 N1 C4 C3 -174.19(15) . . . . ? N2 C3 C4 N1 -158.20(15) . . . . ? C5 C3 C4 N1 60.68(19) . . . . ? C2 C3 C4 N1 -5.69(19) . . . . ? N2 C3 C5 C6 4.31(18) . . . . ? C4 C3 C5 C6 150.32(15) . . . . ? C2 C3 C5 C6 -113.07(16) . . . . ? N2 C3 C5 C2 117.39(15) . . . . ? C4 C3 C5 C2 -96.61(17) . . . . ? C1 C2 C5 C6 -175.89(16) . . . . ? C3 C2 C5 C6 91.46(18) . . . . ? C1 C2 C5 C3 92.65(16) . . . . ? C3 C5 C6 C7 -176.8(2) . . . . ? C2 C5 C6 C7 119.8(2) . . . . ? C3 C5 C6 C11 -1.5(2) . . . . ? C2 C5 C6 C11 -65.0(2) . . . . ? C11 C6 C7 C8 0.8(3) . . . . ? C5 C6 C7 C8 175.6(2) . . . . ? C6 C7 C8 C9 -0.4(4) . . . . ? C7 C8 C9 C10 -0.5(4) . . . . ? C8 C9 C10 C11 0.9(4) . . . . ? C7 C6 C11 C10 -0.4(3) . . . . ? C5 C6 C11 C10 -176.05(19) . . . . ? C7 C6 C11 N2 173.84(18) . . . . ? C5 C6 C11 N2 -1.9(2) . . . . ? C9 C10 C11 C6 -0.5(3) . . . . ? C9 C10 C11 N2 -173.6(2) . . . . ? C3 N2 C11 C6 4.6(2) . . . . ? S1 N2 C11 C6 142.66(14) . . . . ? C3 N2 C11 C10 178.3(2) . . . . ? S1 N2 C11 C10 -43.6(3) . . . . ? C1 N1 C12 Si1 87.89(19) . . . . ? C4 N1 C12 Si1 -91.11(17) . . . . ? C1 N1 C12 Si2 -48.9(2) . . . . ? C4 N1 C12 Si2 132.08(15) . . . . ? C14 Si1 C12 N1 -58.33(16) . . . . ? C13 Si1 C12 N1 61.23(16) . . . . ? C15 Si1 C12 N1 179.05(15) . . . . ? C14 Si1 C12 Si2 76.00(14) . . . . ? C13 Si1 C12 Si2 -164.43(12) . . . . ? C15 Si1 C12 Si2 -46.62(16) . . . . ? C16 Si2 C12 N1 94.43(15) . . . . ? C18 Si2 C12 N1 -31.07(16) . . . . ? C17 Si2 C12 N1 -146.61(15) . . . . ? C16 Si2 C12 Si1 -38.71(15) . . . . ? C18 Si2 C12 Si1 -164.22(12) . . . . ? C17 Si2 C12 Si1 80.24(15) . . . . ? O2 S1 C19B C20B -37.9(7) . . . . ? O3 S1 C19B C20B -171.3(5) . . . . ? N2 S1 C19B C20B 77.6(6) . . . . ? O2 S1 C19B C24B 149.2(4) . . . . ? O3 S1 C19B C24B 15.8(6) . . . . ? N2 S1 C19B C24B -95.3(5) . . . . ? C19A S1 C19B C24B 155(6) . . . . ? C24B C19B C20B C21B 0.0 . . . . ? S1 C19B C20B C21B -172.9(9) . . . . ? C19B C20B C21B C22B 0.0 . . . . ? C20B C21B C22B C23B 0.0 . . . . ? C21B C22B C23B C24B 0.0 . . . . ? C20B C19B C24B C23B 0.0 . . . . ? S1 C19B C24B C23B 172.8(9) . . . . ? C22B C23B C24B C19B 0.0 . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.68 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.197 _refine_diff_density_min -0.453 _refine_diff_density_rms 0.057 data_aw2 _database_code_depnum_ccdc_archive 'CCDC 863240' #TrackingRef '- Compound_34.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point 179(181) _chemical_formula_moiety 'C20 H32 N2 O4 S Si2' _chemical_formula_sum 'C20 H32 N2 O4 S Si2' _chemical_formula_weight 452.72 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' S S 0.1246 0.1234 '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)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 9.0478(9) _cell_length_b 18.6125(18) _cell_length_c 14.1521(14) _cell_angle_alpha 90.00 _cell_angle_beta 96.3590(10) _cell_angle_gamma 90.00 _cell_volume 2368.6(4) _cell_formula_units_Z 4 _cell_measurement_temperature 193(2) _cell_measurement_reflns_used 4166 _cell_measurement_theta_min 2.52 _cell_measurement_theta_max 27.44 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.47 _exptl_crystal_size_min 0.31 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.270 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 968 _exptl_absorpt_coefficient_mu 0.265 _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 193(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 15535 _diffrn_reflns_av_R_equivalents 0.0176 _diffrn_reflns_av_sigmaI/netI 0.0185 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.81 _diffrn_reflns_theta_max 27.48 _reflns_number_total 5381 _reflns_number_gt 4604 _reflns_threshold_expression >2\s(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _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^ > 2\s(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^)+(0.0669P)^2^+0.9510P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5381 _refine_ls_number_parameters 262 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0479 _refine_ls_R_factor_gt 0.0403 _refine_ls_wR_factor_ref 0.1152 _refine_ls_wR_factor_gt 0.1086 _refine_ls_goodness_of_fit_ref 1.045 _refine_ls_restrained_S_all 1.045 _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 C1 C 0.45931(16) 0.06218(8) 0.67512(10) 0.0242(3) Uani 1 1 d . . . C2 C 0.31918(17) 0.03984(9) 0.69304(11) 0.0290(3) Uani 1 1 d . . . H2 H 0.2359 0.0709 0.6810 0.035 Uiso 1 1 calc R . . C3 C 0.30222(19) -0.02902(10) 0.72908(12) 0.0350(4) Uani 1 1 d . . . H3 H 0.2068 -0.0450 0.7420 0.042 Uiso 1 1 calc R . . C4 C 0.4242(2) -0.07424(10) 0.74609(13) 0.0360(4) Uani 1 1 d . . . H4 H 0.4105 -0.1215 0.7690 0.043 Uiso 1 1 calc R . . C5 C 0.56695(18) -0.05184(9) 0.73020(12) 0.0309(3) Uani 1 1 d . . . H5 H 0.6504 -0.0828 0.7423 0.037 Uiso 1 1 calc R . . C6 C 0.58197(15) 0.01710(8) 0.69621(10) 0.0229(3) Uani 1 1 d . . . C7 C 0.50680(16) 0.13126(8) 0.63557(11) 0.0237(3) Uani 1 1 d . . . H7 H 0.4651 0.1777 0.6562 0.028 Uiso 1 1 calc R . . C8 C 0.67267(15) 0.12271(8) 0.63324(10) 0.0216(3) Uani 1 1 d . . . C9 C 0.57195(16) 0.12613(8) 0.54053(10) 0.0248(3) Uani 1 1 d . . . H9 H 0.5545 0.0828 0.4990 0.030 Uiso 1 1 calc R . . C10 C 0.60631(17) 0.19733(8) 0.49974(11) 0.0265(3) Uani 1 1 d . . . C11 C 0.77174(16) 0.18854(8) 0.64203(10) 0.0239(3) Uani 1 1 d . . . H11 H 0.8768 0.1740 0.6363 0.029 Uiso 1 1 calc R . . C12 C 0.7644(2) 0.22768(9) 0.73608(11) 0.0319(4) Uani 1 1 d . . . H12A H 0.6670 0.2520 0.7356 0.038 Uiso 1 1 calc R . . H12B H 0.7742 0.1927 0.7890 0.038 Uiso 1 1 calc R . . C13 C 0.77606(18) 0.30119(8) 0.53419(11) 0.0272(3) Uani 1 1 d . . . H13 H 0.8276 0.3183 0.5962 0.033 Uiso 1 1 calc R . . C14 C 0.7881(2) -0.04018(12) 0.54288(15) 0.0459(5) Uani 1 1 d . . . H14A H 0.7564 -0.0066 0.4913 0.069 Uiso 1 1 calc R . . H14B H 0.7030 -0.0692 0.5572 0.069 Uiso 1 1 calc R . . H14C H 0.8659 -0.0718 0.5234 0.069 Uiso 1 1 calc R . . C15 C 0.8644(3) 0.24231(18) 0.3433(2) 0.0793(9) Uani 1 1 d . . . H15A H 0.8222 0.1956 0.3578 0.119 Uiso 1 1 calc R . . H15B H 0.9475 0.2351 0.3054 0.119 Uiso 1 1 calc R . . H15C H 0.7877 0.2716 0.3072 0.119 Uiso 1 1 calc R . . C16 C 1.0124(2) 0.37809(12) 0.43097(17) 0.0522(5) Uani 1 1 d . . . H16A H 1.0492 0.4015 0.4910 0.078 Uiso 1 1 calc R . . H16B H 0.9356 0.4081 0.3963 0.078 Uiso 1 1 calc R . . H16C H 1.0948 0.3715 0.3923 0.078 Uiso 1 1 calc R . . C17 C 1.0837(3) 0.23459(14) 0.5216(2) 0.0677(8) Uani 1 1 d . . . H17A H 1.0448 0.1872 0.5364 0.102 Uiso 1 1 calc R . . H17B H 1.1206 0.2591 0.5808 0.102 Uiso 1 1 calc R . . H17C H 1.1652 0.2288 0.4821 0.102 Uiso 1 1 calc R . . C18 C 0.5734(3) 0.38459(11) 0.37008(14) 0.0485(5) Uani 1 1 d . . . H18A H 0.6621 0.3940 0.3381 0.073 Uiso 1 1 calc R . . H18B H 0.5044 0.4251 0.3597 0.073 Uiso 1 1 calc R . . H18C H 0.5248 0.3407 0.3442 0.073 Uiso 1 1 calc R . . C19 C 0.7127(3) 0.46048(10) 0.54299(15) 0.0480(5) Uani 1 1 d . . . H19A H 0.7989 0.4711 0.5091 0.072 Uiso 1 1 calc R . . H19B H 0.7445 0.4573 0.6113 0.072 Uiso 1 1 calc R . . H19C H 0.6389 0.4989 0.5311 0.072 Uiso 1 1 calc R . . C20 C 0.4652(2) 0.35440(12) 0.56648(16) 0.0488(5) Uani 1 1 d . . . H20A H 0.4195 0.3087 0.5448 0.073 Uiso 1 1 calc R . . H20B H 0.3923 0.3932 0.5548 0.073 Uiso 1 1 calc R . . H20C H 0.4984 0.3515 0.6347 0.073 Uiso 1 1 calc R . . N2 N 0.71329(14) 0.23032(7) 0.55713(9) 0.0249(3) Uani 1 1 d . . . N3 N 0.71636(13) 0.05447(7) 0.67882(9) 0.0222(3) Uani 1 1 d . . . O1 O 0.54452(14) 0.22275(7) 0.42481(8) 0.0364(3) Uani 1 1 d . . . O2 O 0.90401(13) -0.04167(7) 0.71836(10) 0.0396(3) Uani 1 1 d . . . O3 O 0.96170(13) 0.06006(7) 0.61702(9) 0.0358(3) Uani 1 1 d . . . O4 O 0.88005(18) 0.27889(7) 0.74983(9) 0.0510(4) Uani 1 1 d . . . H4B H 0.8755 0.3003 0.8017 0.076 Uiso 1 1 calc R . . S1 S 0.85819(4) 0.00820(2) 0.64450(3) 0.02588(11) Uani 1 1 d . . . Si2 Si 0.62853(5) 0.37305(3) 0.49991(3) 0.03238(13) Uani 1 1 d . . . Si3 Si 0.93212(6) 0.28909(3) 0.45609(4) 0.04068(14) Uani 1 1 d . . . 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 0.0236(7) 0.0263(7) 0.0225(7) -0.0017(6) 0.0020(5) -0.0006(6) C2 0.0206(7) 0.0378(9) 0.0287(7) -0.0017(6) 0.0031(6) -0.0006(6) C3 0.0256(8) 0.0422(9) 0.0379(9) 0.0012(7) 0.0064(7) -0.0079(7) C4 0.0349(9) 0.0316(9) 0.0423(9) 0.0047(7) 0.0080(7) -0.0081(7) C5 0.0274(8) 0.0275(8) 0.0376(9) 0.0024(6) 0.0027(6) -0.0003(6) C6 0.0188(7) 0.0272(7) 0.0231(7) -0.0018(6) 0.0034(5) -0.0021(5) C7 0.0175(7) 0.0268(7) 0.0265(7) 0.0007(6) 0.0005(5) 0.0014(5) C8 0.0185(7) 0.0225(7) 0.0233(7) -0.0004(5) -0.0002(5) 0.0010(5) C9 0.0228(7) 0.0270(7) 0.0238(7) -0.0006(6) -0.0012(6) -0.0026(5) C10 0.0254(7) 0.0296(8) 0.0240(7) 0.0006(6) 0.0010(6) -0.0019(6) C11 0.0220(7) 0.0242(7) 0.0246(7) 0.0018(6) -0.0016(5) -0.0018(5) C12 0.0389(9) 0.0287(8) 0.0262(8) -0.0021(6) -0.0041(6) -0.0037(7) C13 0.0283(8) 0.0253(7) 0.0276(7) 0.0025(6) 0.0009(6) -0.0052(6) C14 0.0346(9) 0.0561(12) 0.0472(11) -0.0265(9) 0.0054(8) 0.0018(9) C15 0.0734(17) 0.100(2) 0.0722(17) -0.0405(16) 0.0419(14) -0.0341(16) C16 0.0464(11) 0.0542(13) 0.0578(13) 0.0107(10) 0.0140(10) -0.0150(10) C17 0.0434(12) 0.0522(13) 0.113(2) 0.0198(14) 0.0351(13) 0.0099(10) C18 0.0583(13) 0.0447(11) 0.0391(10) 0.0143(8) -0.0102(9) -0.0071(9) C19 0.0608(13) 0.0297(9) 0.0508(11) 0.0039(8) -0.0059(10) -0.0001(9) C20 0.0445(11) 0.0438(11) 0.0601(13) 0.0118(9) 0.0143(9) 0.0107(9) N2 0.0248(6) 0.0247(6) 0.0244(6) 0.0032(5) -0.0008(5) -0.0020(5) N3 0.0181(6) 0.0223(6) 0.0263(6) 0.0007(5) 0.0028(5) 0.0009(4) O1 0.0400(7) 0.0401(7) 0.0263(6) 0.0072(5) -0.0084(5) -0.0053(5) O2 0.0320(6) 0.0374(7) 0.0489(7) 0.0092(6) 0.0031(5) 0.0113(5) O3 0.0222(5) 0.0363(6) 0.0505(7) 0.0000(5) 0.0113(5) -0.0002(5) O4 0.0755(10) 0.0402(7) 0.0317(7) 0.0042(5) -0.0191(6) -0.0276(7) S1 0.01878(18) 0.0279(2) 0.0309(2) -0.00300(14) 0.00224(14) 0.00233(13) Si2 0.0351(3) 0.0287(2) 0.0322(2) 0.00781(18) -0.00088(19) -0.00072(18) Si3 0.0370(3) 0.0396(3) 0.0480(3) -0.0020(2) 0.0160(2) -0.0099(2) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 C1 C2 1.384(2) . ? C1 C6 1.397(2) . ? C1 C7 1.485(2) . ? C2 C3 1.394(2) . ? C2 H2 0.9500 . ? C3 C4 1.388(3) . ? C3 H3 0.9500 . ? C4 C5 1.399(2) . ? C4 H4 0.9500 . ? C5 C6 1.382(2) . ? C5 H5 0.9500 . ? C6 N3 1.4454(18) . ? C7 C8 1.5132(19) . ? C7 C9 1.530(2) . ? C7 H7 1.0000 . ? C8 N3 1.4591(18) . ? C8 C9 1.5136(19) . ? C8 C11 1.515(2) . ? C9 C10 1.492(2) . ? C9 H9 1.0000 . ? C10 O1 1.2367(19) . ? C10 N2 1.3415(19) . ? C11 N2 1.4790(18) . ? C11 C12 1.525(2) . ? C11 H11 1.0000 . ? C12 O4 1.413(2) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 N2 1.4862(19) . ? C13 Si3 1.9004(17) . ? C13 Si2 1.9138(17) . ? C13 H13 1.0000 . ? C14 S1 1.7547(18) . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C15 Si3 1.862(3) . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C16 Si3 1.859(2) . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C17 Si3 1.868(3) . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C18 Si2 1.8621(19) . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C19 Si2 1.870(2) . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? C20 Si2 1.871(2) . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? N3 S1 1.6621(13) . ? O2 S1 1.4248(13) . ? O3 S1 1.4286(12) . ? O4 H4B 0.8400 . ? 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 C2 C1 C6 120.16(14) . . ? C2 C1 C7 129.68(14) . . ? C6 C1 C7 110.15(13) . . ? C1 C2 C3 118.91(15) . . ? C1 C2 H2 120.5 . . ? C3 C2 H2 120.5 . . ? C4 C3 C2 120.23(15) . . ? C4 C3 H3 119.9 . . ? C2 C3 H3 119.9 . . ? C3 C4 C5 121.46(16) . . ? C3 C4 H4 119.3 . . ? C5 C4 H4 119.3 . . ? C6 C5 C4 117.44(15) . . ? C6 C5 H5 121.3 . . ? C4 C5 H5 121.3 . . ? C5 C6 C1 121.70(14) . . ? C5 C6 N3 128.53(14) . . ? C1 C6 N3 109.75(13) . . ? C1 C7 C8 104.25(12) . . ? C1 C7 C9 115.66(13) . . ? C8 C7 C9 59.65(9) . . ? C1 C7 H7 120.3 . . ? C8 C7 H7 120.3 . . ? C9 C7 H7 120.3 . . ? N3 C8 C7 107.63(12) . . ? N3 C8 C9 121.84(12) . . ? C7 C8 C9 60.73(9) . . ? N3 C8 C11 122.60(11) . . ? C7 C8 C11 119.49(12) . . ? C9 C8 C11 109.33(12) . . ? C10 C9 C8 103.98(12) . . ? C10 C9 C7 113.68(13) . . ? C8 C9 C7 59.62(9) . . ? C10 C9 H9 121.0 . . ? C8 C9 H9 121.0 . . ? C7 C9 H9 121.0 . . ? O1 C10 N2 124.84(15) . . ? O1 C10 C9 125.30(14) . . ? N2 C10 C9 109.86(12) . . ? N2 C11 C8 101.74(11) . . ? N2 C11 C12 114.30(13) . . ? C8 C11 C12 112.05(13) . . ? N2 C11 H11 109.5 . . ? C8 C11 H11 109.5 . . ? C12 C11 H11 109.5 . . ? O4 C12 C11 109.82(14) . . ? O4 C12 H12A 109.7 . . ? C11 C12 H12A 109.7 . . ? O4 C12 H12B 109.7 . . ? C11 C12 H12B 109.7 . . ? H12A C12 H12B 108.2 . . ? N2 C13 Si3 110.38(11) . . ? N2 C13 Si2 113.77(10) . . ? Si3 C13 Si2 118.54(8) . . ? N2 C13 H13 104.1 . . ? Si3 C13 H13 104.1 . . ? Si2 C13 H13 104.1 . . ? S1 C14 H14A 109.5 . . ? S1 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? S1 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? Si3 C15 H15A 109.5 . . ? Si3 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? Si3 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? Si3 C16 H16A 109.5 . . ? Si3 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? Si3 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? Si3 C17 H17A 109.5 . . ? Si3 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? Si3 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? Si2 C18 H18A 109.5 . . ? Si2 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? Si2 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? Si2 C19 H19A 109.5 . . ? Si2 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? Si2 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? Si2 C20 H20A 109.5 . . ? Si2 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? Si2 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C10 N2 C11 114.85(12) . . ? C10 N2 C13 122.79(12) . . ? C11 N2 C13 122.22(12) . . ? C6 N3 C8 107.60(11) . . ? C6 N3 S1 119.45(10) . . ? C8 N3 S1 120.13(10) . . ? C12 O4 H4B 109.5 . . ? O2 S1 O3 119.58(8) . . ? O2 S1 N3 107.13(7) . . ? O3 S1 N3 106.26(7) . . ? O2 S1 C14 108.44(10) . . ? O3 S1 C14 108.17(10) . . ? N3 S1 C14 106.55(8) . . ? C18 Si2 C19 106.03(9) . . ? C18 Si2 C20 112.23(10) . . ? C19 Si2 C20 108.25(11) . . ? C18 Si2 C13 115.70(9) . . ? C19 Si2 C13 106.14(8) . . ? C20 Si2 C13 108.07(8) . . ? C16 Si3 C15 110.56(13) . . ? C16 Si3 C17 107.33(11) . . ? C15 Si3 C17 109.02(16) . . ? C16 Si3 C13 109.68(9) . . ? C15 Si3 C13 111.04(10) . . ? C17 Si3 C13 109.12(10) . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.448 _refine_diff_density_min -0.413 _refine_diff_density_rms 0.057