# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2003 data_global _journal_coden_Cambridge 182 loop_ _publ_author_name 'Jeremy Kilburn' 'Malcolm Berry' 'Simon J. Coles' 'Michael B. Hursthouse' 'Lee Patient' _publ_contact_author_name 'Prof Jeremy Kilburn' _publ_contact_author_address ; Department of Chemistry Southampton University Highfield Southampton SO17 1BJ UNITED KINGDOM ; _publ_contact_author_email JDK1@SOTON.AC.UK _publ_requested_journal 'Chemical Communications' _publ_section_title ; Lewis acid mediated cyclisations of silylated methylenecyclopropyl hydrazones ; data_11a _database_code_CSD 212875 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H28 N2 O2 S Si' _chemical_formula_weight 364.57 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 14.291(3) _cell_length_b 11.709(2) _cell_length_c 13.341(3) _cell_angle_alpha 90.00 _cell_angle_beta 115.86(3) _cell_angle_gamma 90.00 _cell_volume 2008.9(7) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 35413 _cell_measurement_theta_min 1.02 _cell_measurement_theta_max 30.51 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.205 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 784 _exptl_absorpt_coefficient_mu 0.233 _exptl_absorpt_correction_type multi-scans _exptl_absorpt_correction_T_min 0.9637 _exptl_absorpt_correction_T_max 0.9907 _exptl_absorpt_process_details 'SORTAV (Blessing, 1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Nonius FR591 rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD Area Detector' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_decay_% negligible _diffrn_reflns_number 9715 _diffrn_reflns_av_R_equivalents 0.0857 _diffrn_reflns_av_sigmaI/netI 0.1025 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.35 _diffrn_reflns_theta_max 27.49 _reflns_number_total 3752 _reflns_number_gt 2320 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, 1998)' _computing_cell_refinement 'DENZO, COLLECT' _computing_data_reduction 'DENZO, COLLECT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON (Spek, 1991)' _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1126P)^2^+0.0935P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment riding _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0043(18) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3752 _refine_ls_number_parameters 223 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1251 _refine_ls_R_factor_gt 0.0691 _refine_ls_wR_factor_ref 0.1942 _refine_ls_wR_factor_gt 0.1625 _refine_ls_goodness_of_fit_ref 1.010 _refine_ls_restrained_S_all 1.010 _refine_ls_shift/su_max 0.011 _refine_ls_shift/su_mean 0.001 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 -0.1793(3) 0.0215(4) 0.3909(4) 0.0450(11) Uani 1 1 d . . . H1A H -0.1488 0.0600 0.4634 0.067 Uiso 1 1 calc R . . H1B H -0.1786 -0.0613 0.4021 0.067 Uiso 1 1 calc R . . H1C H -0.2512 0.0475 0.3483 0.067 Uiso 1 1 calc R . . C2 C -0.1173(3) 0.0496(3) 0.3281(3) 0.0326(9) Uani 1 1 d . . . C3 C -0.0284(3) 0.1171(3) 0.3750(3) 0.0378(10) Uani 1 1 d . . . H3 H -0.0056 0.1445 0.4489 0.045 Uiso 1 1 calc R . . C4 C 0.0277(3) 0.1451(3) 0.3154(3) 0.0335(9) Uani 1 1 d . . . H4 H 0.0881 0.1916 0.3485 0.040 Uiso 1 1 calc R . . C5 C -0.0045(3) 0.1053(3) 0.2083(3) 0.0273(8) Uani 1 1 d . . . C6 C -0.0931(3) 0.0358(3) 0.1597(3) 0.0310(9) Uani 1 1 d . . . H6 H -0.1153 0.0074 0.0862 0.037 Uiso 1 1 calc R . . C7 C -0.1472(3) 0.0096(3) 0.2202(3) 0.0364(10) Uani 1 1 d . . . H7 H -0.2072 -0.0375 0.1872 0.044 Uiso 1 1 calc R . . C8 C 0.2365(3) -0.0969(3) 0.2888(3) 0.0289(9) Uani 1 1 d . . . C9 C 0.1439(3) -0.1309(3) 0.3082(3) 0.0370(10) Uani 1 1 d . . . H9A H 0.1365 -0.0778 0.3610 0.056 Uiso 1 1 calc R . . H9B H 0.1541 -0.2085 0.3387 0.056 Uiso 1 1 calc R . . H9C H 0.0810 -0.1286 0.2374 0.056 Uiso 1 1 calc R . . C10 C 0.3401(3) -0.0883(3) 0.3932(3) 0.0397(10) Uani 1 1 d . . . H10A H 0.3714 -0.1647 0.4178 0.048 Uiso 1 1 calc R . . H10B H 0.3311 -0.0510 0.4550 0.048 Uiso 1 1 calc R . . C11 C 0.4076(3) -0.0143(3) 0.3541(3) 0.0405(11) Uani 1 1 d . . . H11A H 0.4335 0.0545 0.4012 0.049 Uiso 1 1 calc R . . H11B H 0.4676 -0.0583 0.3562 0.049 Uiso 1 1 calc R . . C12 C 0.3325(3) 0.0183(3) 0.2334(3) 0.0314(9) Uani 1 1 d . . . C13 C 0.3161(3) -0.0896(3) 0.1642(3) 0.0312(9) Uani 1 1 d . . . C14 C 0.3443(3) -0.1124(4) 0.0847(4) 0.0471(12) Uani 1 1 d . . . H14A H 0.3251 -0.1829 0.0457 0.057 Uiso 1 1 calc R . . H14B H 0.3838 -0.0583 0.0662 0.057 Uiso 1 1 calc R . . C15 C 0.2530(3) -0.1693(3) 0.2008(3) 0.0335(9) Uani 1 1 d . . . H15A H 0.2919 -0.2402 0.2339 0.040 Uiso 1 1 calc R . . H15B H 0.1859 -0.1892 0.1376 0.040 Uiso 1 1 calc R . . C16 C 0.3777(3) 0.2708(4) 0.2887(4) 0.0481(11) Uani 1 1 d . . . H16A H 0.3959 0.3438 0.2657 0.072 Uiso 1 1 calc R . . H16B H 0.4303 0.2511 0.3635 0.072 Uiso 1 1 calc R . . H16C H 0.3096 0.2774 0.2893 0.072 Uiso 1 1 calc R . . C17 C 0.5071(3) 0.1351(4) 0.2023(5) 0.0602(14) Uani 1 1 d . . . H17A H 0.5056 0.0777 0.1481 0.090 Uiso 1 1 calc R . . H17B H 0.5524 0.1086 0.2778 0.090 Uiso 1 1 calc R . . H17C H 0.5339 0.2073 0.1881 0.090 Uiso 1 1 calc R . . C18 C 0.2867(3) 0.2019(4) 0.0444(3) 0.0447(11) Uani 1 1 d . . . H18A H 0.3150 0.2709 0.0261 0.067 Uiso 1 1 calc R . . H18B H 0.2170 0.2179 0.0378 0.067 Uiso 1 1 calc R . . H18C H 0.2828 0.1405 -0.0073 0.067 Uiso 1 1 calc R . . N1 N 0.1458(2) 0.0407(2) 0.1406(2) 0.0240(7) Uani 1 1 d . . . H1 H 0.1376 -0.0017 0.0829 0.029 Uiso 1 1 calc R . . N2 N 0.2319(2) 0.0237(2) 0.2464(2) 0.0254(7) Uani 1 1 d . . . O1 O -0.00923(18) 0.13760(18) 0.0138(2) 0.0293(6) Uani 1 1 d . . . O2 O 0.12035(18) 0.24305(19) 0.1759(2) 0.0371(7) Uani 1 1 d . . . Si1 Si 0.37260(8) 0.15719(9) 0.18889(10) 0.0358(4) Uani 1 1 d . . . S1 S 0.06326(7) 0.14085(7) 0.13027(8) 0.0269(3) 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 0.049(3) 0.045(3) 0.043(3) 0.005(2) 0.023(2) 0.0100(19) C2 0.035(2) 0.029(2) 0.035(2) 0.0031(17) 0.0168(19) 0.0102(16) C3 0.042(2) 0.033(2) 0.034(2) -0.0019(18) 0.012(2) 0.0104(18) C4 0.028(2) 0.028(2) 0.034(2) -0.0035(17) 0.0039(18) 0.0058(15) C5 0.0222(19) 0.0223(19) 0.032(2) -0.0024(16) 0.0069(17) 0.0054(14) C6 0.029(2) 0.033(2) 0.030(2) -0.0083(17) 0.0115(18) -0.0048(16) C7 0.033(2) 0.038(2) 0.038(3) -0.0034(19) 0.016(2) -0.0055(17) C8 0.0211(19) 0.0238(19) 0.035(2) 0.0031(16) 0.0057(17) -0.0019(14) C9 0.039(2) 0.027(2) 0.046(3) 0.0062(18) 0.018(2) -0.0012(16) C10 0.032(2) 0.039(2) 0.036(2) 0.0087(18) 0.0045(19) 0.0002(17) C11 0.023(2) 0.035(2) 0.051(3) 0.0063(19) 0.004(2) -0.0027(16) C12 0.0162(19) 0.035(2) 0.039(2) 0.0009(17) 0.0091(17) 0.0001(15) C13 0.0189(19) 0.029(2) 0.040(2) 0.0010(17) 0.0075(18) 0.0059(15) C14 0.039(3) 0.042(2) 0.064(3) -0.007(2) 0.025(2) -0.0022(19) C15 0.0211(19) 0.0251(19) 0.045(3) 0.0033(17) 0.0061(18) 0.0051(15) C16 0.038(2) 0.041(2) 0.057(3) -0.006(2) 0.012(2) -0.0113(18) C17 0.031(2) 0.059(3) 0.091(4) -0.001(3) 0.026(3) -0.010(2) C18 0.044(3) 0.044(2) 0.046(3) 0.005(2) 0.019(2) -0.0063(19) N1 0.0191(15) 0.0221(15) 0.0276(18) 0.0001(12) 0.0071(14) 0.0021(11) N2 0.0171(15) 0.0255(16) 0.0286(18) 0.0023(13) 0.0052(14) -0.0019(11) O1 0.0222(13) 0.0271(14) 0.0311(15) 0.0049(11) 0.0047(12) 0.0024(10) O2 0.0267(14) 0.0202(13) 0.0544(19) -0.0083(12) 0.0085(13) -0.0055(10) Si1 0.0225(6) 0.0335(6) 0.0480(8) 0.0002(5) 0.0122(5) -0.0073(4) S1 0.0201(5) 0.0197(5) 0.0364(6) -0.0009(4) 0.0080(4) 0.0001(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 C1 C2 1.497(5) . ? C2 C3 1.392(5) . ? C2 C7 1.392(5) . ? C3 C4 1.393(5) . ? C4 C5 1.377(5) . ? C5 C6 1.403(5) . ? C5 S1 1.754(4) . ? C6 C7 1.374(5) . ? C8 C9 1.508(5) . ? C8 N2 1.512(4) . ? C8 C10 1.531(5) . ? C8 C15 1.548(5) . ? C10 C11 1.546(5) . ? C11 C12 1.543(5) . ? C12 C13 1.522(5) . ? C12 N2 1.523(4) . ? C12 Si1 1.903(4) . ? C13 C14 1.316(6) . ? C13 C15 1.518(5) . ? C16 Si1 1.861(4) . ? C17 Si1 1.870(4) . ? C18 Si1 1.853(4) . ? N1 N2 1.424(4) . ? N1 S1 1.627(3) . ? O1 S1 1.444(3) . ? O2 S1 1.427(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 C3 C2 C7 117.6(4) . . ? C3 C2 C1 121.4(4) . . ? C7 C2 C1 121.0(4) . . ? C2 C3 C4 121.2(4) . . ? C5 C4 C3 119.8(4) . . ? C4 C5 C6 120.2(4) . . ? C4 C5 S1 120.9(3) . . ? C6 C5 S1 118.9(3) . . ? C7 C6 C5 118.9(4) . . ? C6 C7 C2 122.3(4) . . ? C9 C8 N2 114.4(3) . . ? C9 C8 C10 115.8(3) . . ? N2 C8 C10 98.4(3) . . ? C9 C8 C15 114.9(3) . . ? N2 C8 C15 102.9(3) . . ? C10 C8 C15 108.6(3) . . ? C8 C10 C11 103.2(3) . . ? C12 C11 C10 103.8(3) . . ? C13 C12 N2 101.6(3) . . ? C13 C12 C11 106.3(3) . . ? N2 C12 C11 98.8(3) . . ? C13 C12 Si1 120.5(3) . . ? N2 C12 Si1 115.3(2) . . ? C11 C12 Si1 111.7(2) . . ? C14 C13 C15 124.6(4) . . ? C14 C13 C12 129.6(4) . . ? C15 C13 C12 105.7(3) . . ? C13 C15 C8 102.5(3) . . ? N2 N1 S1 117.7(2) . . ? N1 N2 C8 112.3(2) . . ? N1 N2 C12 110.1(3) . . ? C8 N2 C12 96.6(2) . . ? C18 Si1 C16 110.1(2) . . ? C18 Si1 C17 109.0(2) . . ? C16 Si1 C17 108.2(2) . . ? C18 Si1 C12 114.41(17) . . ? C16 Si1 C12 108.12(19) . . ? C17 Si1 C12 106.77(19) . . ? O2 S1 O1 119.33(15) . . ? O2 S1 N1 108.07(15) . . ? O1 S1 N1 103.05(14) . . ? O2 S1 C5 107.87(17) . . ? O1 S1 C5 108.05(16) . . ? N1 S1 C5 110.27(15) . . ? _diffrn_measured_fraction_theta_max 0.815 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.815 _refine_diff_density_max 0.722 _refine_diff_density_min -0.564 _refine_diff_density_rms 0.086 data_11b _database_code_CSD 212876 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C17 H26 N2 O2 S Si' _chemical_formula_weight 350.55 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.5369(4) _cell_length_b 9.7508(4) _cell_length_c 12.0846(7) _cell_angle_alpha 113.047(2) _cell_angle_beta 96.842(2) _cell_angle_gamma 93.051(4) _cell_volume 913.55(8) _cell_formula_units_Z 2 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 26695 _cell_measurement_theta_min 1.02 _cell_measurement_theta_max 27.48 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.274 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 376 _exptl_absorpt_coefficient_mu 0.253 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9324 _exptl_absorpt_correction_T_max 0.9800 _exptl_absorpt_process_details 'SORTAV Blessing (1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Nonius FR591 rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_decay_% negligible _diffrn_reflns_number 12944 _diffrn_reflns_av_R_equivalents 0.0780 _diffrn_reflns_av_sigmaI/netI 0.0637 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.28 _diffrn_reflns_theta_max 27.45 _reflns_number_total 4105 _reflns_number_gt 3222 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, 1998)' _computing_cell_refinement 'DENZO & COLLECT' _computing_data_reduction 'DENZO & COLLECT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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^ > 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^)+(0.0914P)^2^+0.4437P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment riding _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.006(5) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 4105 _refine_ls_number_parameters 217 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0722 _refine_ls_R_factor_gt 0.0539 _refine_ls_wR_factor_ref 0.1564 _refine_ls_wR_factor_gt 0.1429 _refine_ls_goodness_of_fit_ref 1.009 _refine_ls_restrained_S_all 1.009 _refine_ls_shift/su_max 0.072 _refine_ls_shift/su_mean 0.002 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 -0.4482(3) 0.4640(3) 0.3396(3) 0.0381(6) Uani 1 1 d . . . H1A H -0.5386 0.4308 0.3694 0.057 Uiso 1 1 calc R . . H1B H -0.4755 0.4386 0.2523 0.057 Uiso 1 1 calc R . . H1C H -0.4225 0.5727 0.3831 0.057 Uiso 1 1 calc R . . C2 C -0.3070(3) 0.3868(3) 0.3613(2) 0.0309(5) Uani 1 1 d . . . C3 C -0.1639(4) 0.4155(3) 0.3276(3) 0.0506(8) Uani 1 1 d . . . H3 H -0.1549 0.4859 0.2916 0.061 Uiso 1 1 calc R . . C4 C -0.0327(3) 0.3438(3) 0.3454(3) 0.0460(7) Uani 1 1 d . . . H4 H 0.0650 0.3648 0.3218 0.055 Uiso 1 1 calc R . . C5 C -0.0461(3) 0.2415(2) 0.3978(2) 0.0242(5) Uani 1 1 d . . . C6 C -0.1885(3) 0.2108(3) 0.4329(2) 0.0287(5) Uani 1 1 d . . . H6 H -0.1969 0.1411 0.4695 0.034 Uiso 1 1 calc R . . C7 C -0.3178(3) 0.2828(3) 0.4138(2) 0.0299(5) Uani 1 1 d . . . H7 H -0.4156 0.2611 0.4369 0.036 Uiso 1 1 calc R . . C8 C -0.0991(2) -0.1459(2) 0.1473(2) 0.0276(5) Uani 1 1 d . . . H8 H -0.1899 -0.0893 0.1785 0.033 Uiso 1 1 calc R . . C9 C -0.0879(3) -0.1771(3) 0.0156(2) 0.0313(5) Uani 1 1 d . . . H9A H -0.1061 -0.0880 -0.0023 0.038 Uiso 1 1 calc R . . H9B H -0.1648 -0.2628 -0.0406 0.038 Uiso 1 1 calc R . . C10 C 0.0861(3) -0.2152(3) 0.0067(2) 0.0287(5) Uani 1 1 d . . . H10A H 0.0889 -0.3212 -0.0484 0.034 Uiso 1 1 calc R . . H10B H 0.1449 -0.1497 -0.0231 0.034 Uiso 1 1 calc R . . C11 C 0.1571(2) -0.1858(2) 0.13967(19) 0.0212(4) Uani 1 1 d . . . C12 C -0.0929(3) -0.2938(2) 0.1653(2) 0.0263(5) Uani 1 1 d . . . H12A H -0.1256 -0.2839 0.2437 0.032 Uiso 1 1 calc R . . H12B H -0.1609 -0.3775 0.0981 0.032 Uiso 1 1 calc R . . C13 C 0.0838(3) -0.3161(2) 0.1641(2) 0.0239(5) Uani 1 1 d . . . C14 C 0.1566(3) -0.4198(3) 0.1874(3) 0.0417(6) Uani 1 1 d . . . H14A H 0.2684 -0.4189 0.1906 0.050 Uiso 1 1 calc R . . H14B H 0.0973 -0.4954 0.2011 0.050 Uiso 1 1 calc R . . C15 C 0.4258(3) 0.0379(3) 0.1486(2) 0.0307(5) Uani 1 1 d . . . H15A H 0.3778 0.1197 0.2066 0.046 Uiso 1 1 calc R . . H15B H 0.3823 0.0230 0.0655 0.046 Uiso 1 1 calc R . . H15C H 0.5410 0.0633 0.1621 0.046 Uiso 1 1 calc R . . C16 C 0.4679(3) -0.1160(3) 0.3259(2) 0.0355(6) Uani 1 1 d . . . H16A H 0.5840 -0.1065 0.3333 0.053 Uiso 1 1 calc R . . H16B H 0.4313 -0.2043 0.3395 0.053 Uiso 1 1 calc R . . H16C H 0.4346 -0.0261 0.3865 0.053 Uiso 1 1 calc R . . C17 C 0.4607(3) -0.2953(3) 0.0511(3) 0.0441(7) Uani 1 1 d . . . H17A H 0.4030 -0.3132 -0.0293 0.066 Uiso 1 1 calc R . . H17B H 0.4471 -0.3863 0.0665 0.066 Uiso 1 1 calc R . . H17C H 0.5737 -0.2685 0.0536 0.066 Uiso 1 1 calc R . . N1 N 0.0899(2) -0.0254(2) 0.33419(17) 0.0242(4) Uani 1 1 d . . . N2 N 0.0614(2) -0.0609(2) 0.20614(17) 0.0233(4) Uani 1 1 d . . . O1 O 0.25392(18) 0.21910(17) 0.39503(15) 0.0293(4) Uani 1 1 d . . . O2 O 0.12777(18) 0.15110(17) 0.54365(14) 0.0269(4) Uani 1 1 d . . . Si1 Si 0.38061(7) -0.13740(7) 0.17092(6) 0.0250(2) Uani 1 1 d . . . S1 S 0.12004(6) 0.15244(6) 0.42404(5) 0.02323(19) Uani 1 1 d . . . H1 H 0.029(4) -0.074(3) 0.361(3) 0.040(8) Uiso 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 0.0362(14) 0.0345(13) 0.0448(15) 0.0160(12) 0.0063(11) 0.0147(11) C2 0.0307(13) 0.0246(11) 0.0360(13) 0.0090(10) 0.0091(10) 0.0095(9) C3 0.0468(17) 0.0525(18) 0.082(2) 0.0507(18) 0.0297(15) 0.0215(14) C4 0.0360(15) 0.0501(17) 0.075(2) 0.0433(16) 0.0271(14) 0.0170(12) C5 0.0225(11) 0.0177(10) 0.0320(12) 0.0077(9) 0.0100(9) 0.0046(8) C6 0.0214(11) 0.0266(11) 0.0418(14) 0.0171(10) 0.0069(9) 0.0029(9) C7 0.0208(11) 0.0298(12) 0.0403(14) 0.0142(11) 0.0084(9) 0.0049(9) C8 0.0137(10) 0.0235(11) 0.0413(13) 0.0090(10) 0.0017(9) 0.0026(8) C9 0.0199(11) 0.0324(12) 0.0412(14) 0.0166(11) -0.0037(9) 0.0032(9) C10 0.0217(11) 0.0315(12) 0.0324(12) 0.0141(10) -0.0012(9) 0.0008(9) C11 0.0161(10) 0.0198(10) 0.0264(11) 0.0072(9) 0.0035(8) 0.0051(8) C12 0.0194(11) 0.0232(11) 0.0323(12) 0.0069(9) 0.0038(9) 0.0016(8) C13 0.0211(11) 0.0203(10) 0.0265(11) 0.0054(9) 0.0036(8) 0.0024(8) C14 0.0380(15) 0.0354(14) 0.0528(17) 0.0191(13) 0.0060(12) 0.0042(11) C15 0.0255(12) 0.0314(12) 0.0327(13) 0.0093(10) 0.0093(9) -0.0005(9) C16 0.0252(12) 0.0335(13) 0.0458(15) 0.0164(11) -0.0047(10) 0.0041(10) C17 0.0232(13) 0.0356(14) 0.0596(18) 0.0019(13) 0.0126(11) 0.0083(10) N1 0.0209(9) 0.0175(9) 0.0324(11) 0.0069(8) 0.0082(8) 0.0028(7) N2 0.0150(9) 0.0211(9) 0.0317(10) 0.0080(8) 0.0037(7) 0.0042(7) O1 0.0219(8) 0.0238(8) 0.0393(9) 0.0078(7) 0.0123(7) -0.0014(6) O2 0.0223(8) 0.0237(8) 0.0315(9) 0.0073(7) 0.0054(6) 0.0014(6) Si1 0.0146(3) 0.0234(3) 0.0330(4) 0.0066(3) 0.0037(2) 0.0046(2) S1 0.0167(3) 0.0180(3) 0.0328(3) 0.0067(2) 0.0077(2) 0.00178(19) _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 C1 C2 1.504(3) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C2 C3 1.382(4) . ? C2 C7 1.395(3) . ? C3 C4 1.391(4) . ? C3 H3 0.9500 . ? C4 C5 1.381(3) . ? C4 H4 0.9500 . ? C5 C6 1.389(3) . ? C5 S1 1.763(2) . ? C6 C7 1.383(3) . ? C6 H6 0.9500 . ? C7 H7 0.9500 . ? C8 N2 1.502(3) . ? C8 C9 1.515(3) . ? C8 C12 1.543(3) . ? C8 H8 1.0000 . ? C9 C10 1.556(3) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 C11 1.556(3) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 N2 1.514(3) . ? C11 C13 1.532(3) . ? C11 Si1 1.897(2) . ? C12 C13 1.536(3) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 C14 1.317(3) . ? C14 H14A 0.9500 . ? C14 H14B 0.9500 . ? C15 Si1 1.859(2) . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C16 Si1 1.858(3) . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C17 Si1 1.880(3) . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? N1 N2 1.434(3) . ? N1 S1 1.6319(18) . ? N1 H1 0.86(3) . ? O1 S1 1.4305(15) . ? O2 S1 1.4444(17) . ? 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 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? C3 C2 C7 118.4(2) . . ? C3 C2 C1 120.6(2) . . ? C7 C2 C1 121.0(2) . . ? C2 C3 C4 121.4(2) . . ? C2 C3 H3 119.3 . . ? C4 C3 H3 119.3 . . ? C5 C4 C3 119.2(2) . . ? C5 C4 H4 120.4 . . ? C3 C4 H4 120.4 . . ? C4 C5 C6 120.6(2) . . ? C4 C5 S1 119.81(18) . . ? C6 C5 S1 119.54(17) . . ? C7 C6 C5 119.3(2) . . ? C7 C6 H6 120.3 . . ? C5 C6 H6 120.3 . . ? C6 C7 C2 121.1(2) . . ? C6 C7 H7 119.5 . . ? C2 C7 H7 119.5 . . ? N2 C8 C9 99.68(18) . . ? N2 C8 C12 104.33(17) . . ? C9 C8 C12 108.93(19) . . ? N2 C8 H8 114.2 . . ? C9 C8 H8 114.2 . . ? C12 C8 H8 114.2 . . ? C8 C9 C10 101.99(17) . . ? C8 C9 H9A 111.4 . . ? C10 C9 H9A 111.4 . . ? C8 C9 H9B 111.4 . . ? C10 C9 H9B 111.4 . . ? H9A C9 H9B 109.2 . . ? C11 C10 C9 103.90(18) . . ? C11 C10 H10A 111.0 . . ? C9 C10 H10A 111.0 . . ? C11 C10 H10B 111.0 . . ? C9 C10 H10B 111.0 . . ? H10A C10 H10B 109.0 . . ? N2 C11 C13 101.59(16) . . ? N2 C11 C10 98.79(16) . . ? C13 C11 C10 105.70(17) . . ? N2 C11 Si1 115.98(14) . . ? C13 C11 Si1 119.78(15) . . ? C10 C11 Si1 112.38(14) . . ? C13 C12 C8 101.65(17) . . ? C13 C12 H12A 111.4 . . ? C8 C12 H12A 111.4 . . ? C13 C12 H12B 111.4 . . ? C8 C12 H12B 111.4 . . ? H12A C12 H12B 109.3 . . ? C14 C13 C11 128.0(2) . . ? C14 C13 C12 126.7(2) . . ? C11 C13 C12 105.11(17) . . ? C13 C14 H14A 120.0 . . ? C13 C14 H14B 120.0 . . ? H14A C14 H14B 120.0 . . ? 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 . . ? Si1 C16 H16A 109.5 . . ? Si1 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? Si1 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? Si1 C17 H17A 109.5 . . ? Si1 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? Si1 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? N2 N1 S1 116.40(14) . . ? N2 N1 H1 117.1(19) . . ? S1 N1 H1 111.3(19) . . ? N1 N2 C8 112.19(17) . . ? N1 N2 C11 110.13(16) . . ? C8 N2 C11 96.41(15) . . ? C16 Si1 C15 110.79(11) . . ? C16 Si1 C17 110.90(13) . . ? C15 Si1 C17 108.56(12) . . ? C16 Si1 C11 112.56(11) . . ? C15 Si1 C11 108.15(10) . . ? C17 Si1 C11 105.67(11) . . ? O1 S1 O2 119.10(10) . . ? O1 S1 N1 108.76(10) . . ? O2 S1 N1 102.98(10) . . ? O1 S1 C5 107.67(10) . . ? O2 S1 C5 108.64(10) . . ? N1 S1 C5 109.39(10) . . ? _diffrn_measured_fraction_theta_max 0.983 _diffrn_reflns_theta_full 27.45 _diffrn_measured_fraction_theta_full 0.983 _refine_diff_density_max 1.062 _refine_diff_density_min -0.558 _refine_diff_density_rms 0.077 data_11d _database_code_CSD 212877 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H28 N2 O2 S Si' _chemical_formula_weight 364.57 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.9559(4) _cell_length_b 9.0489(4) _cell_length_c 24.0779(13) _cell_angle_alpha 85.016(2) _cell_angle_beta 88.2630(10) _cell_angle_gamma 87.538(2) _cell_volume 1941.43(16) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 18333 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.247 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 784 _exptl_absorpt_coefficient_mu 0.241 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9312 _exptl_absorpt_correction_T_max 0.9763 _exptl_absorpt_process_details 'SORTAV Blessing (1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Nonius FR591 rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_decay_% negligible _diffrn_reflns_number 13750 _diffrn_reflns_av_R_equivalents 0.0484 _diffrn_reflns_av_sigmaI/netI 0.0608 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -31 _diffrn_reflns_limit_l_max 31 _diffrn_reflns_theta_min 3.14 _diffrn_reflns_theta_max 27.45 _reflns_number_total 6515 _reflns_number_gt 5157 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, 1998)' _computing_cell_refinement 'DENZO & COLLECT' _computing_data_reduction 'DENZO & COLLECT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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^ > 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^)+(0.0902P)^2^+8.2962P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment riding _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.016(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 6515 _refine_ls_number_parameters 442 _refine_ls_number_restraints 18 _refine_ls_R_factor_all 0.1175 _refine_ls_R_factor_gt 0.0984 _refine_ls_wR_factor_ref 0.2550 _refine_ls_wR_factor_gt 0.2430 _refine_ls_goodness_of_fit_ref 1.050 _refine_ls_restrained_S_all 1.049 _refine_ls_shift/su_max 0.230 _refine_ls_shift/su_mean 0.011 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 0.0955(8) 0.2115(8) 0.2132(2) 0.0529(16) Uani 1 1 d . . . H1A H 0.0072 0.2231 0.1899 0.079 Uiso 1 1 calc R . . H1B H 0.0833 0.2769 0.2436 0.079 Uiso 1 1 calc R . . H1C H 0.1067 0.1082 0.2290 0.079 Uiso 1 1 calc R . . C2 C 0.2326(7) 0.2518(6) 0.1783(2) 0.0397(13) Uani 1 1 d . . . C3 C 0.3693(8) 0.2691(7) 0.2025(2) 0.0517(16) Uani 1 1 d . . . H3 H 0.3773 0.2527 0.2418 0.062 Uiso 1 1 calc R . . C4 C 0.4930(7) 0.3097(7) 0.1703(2) 0.0491(16) Uani 1 1 d . . . H4 H 0.5851 0.3226 0.1875 0.059 Uiso 1 1 calc R . . C5 C 0.4830(6) 0.3318(6) 0.1127(2) 0.0326(11) Uani 1 1 d . . . C6 C 0.3477(6) 0.3149(6) 0.0877(2) 0.0322(11) Uani 1 1 d . . . H6 H 0.3399 0.3321 0.0484 0.039 Uiso 1 1 calc R . . C7 C 0.2243(6) 0.2728(6) 0.1203(2) 0.0370(12) Uani 1 1 d . . . H7 H 0.1327 0.2580 0.1031 0.044 Uiso 1 1 calc R . . C8 C 0.4567(6) 0.6934(7) 0.1347(2) 0.0429(14) Uani 1 1 d . . . H8 H 0.3832 0.6190 0.1260 0.051 Uiso 1 1 calc R . . C9 C 0.4427(10) 0.7267(9) 0.1946(3) 0.067(2) Uani 1 1 d . . . H9A H 0.3373 0.7556 0.2033 0.081 Uiso 1 1 calc R . . H9B H 0.4691 0.6354 0.2186 0.081 Uiso 1 1 calc R . . C10 C 0.5385(9) 0.8456(9) 0.2079(3) 0.067(2) Uani 1 1 d . . . H10A H 0.5439 0.8471 0.2489 0.080 Uiso 1 1 calc R . . H10B H 0.4960 0.9429 0.1925 0.080 Uiso 1 1 calc R . . C11 C 0.6924(7) 0.8191(7) 0.1832(2) 0.0458(14) Uani 1 1 d . . . H11A H 0.7435 0.7376 0.2063 0.055 Uiso 1 1 calc R . . H11B H 0.7495 0.9096 0.1855 0.055 Uiso 1 1 calc R . . C12 C 0.6989(6) 0.7792(6) 0.1216(2) 0.0324(11) Uani 1 1 d . . . C13 C 0.6047(7) 0.8929(6) 0.0864(2) 0.0393(13) Uani 1 1 d . . . C14 C 0.4396(8) 0.8388(8) 0.0950(3) 0.0582(19) Uani 1 1 d . . . H14A H 0.3743 0.9140 0.1123 0.070 Uiso 1 1 calc R . . H14B H 0.3973 0.8185 0.0590 0.070 Uiso 1 1 calc R . . C15 C 0.6424(9) 1.0083(8) 0.0559(3) 0.0618(19) Uani 1 1 d . . . H15A H 0.7443 1.0337 0.0528 0.074 Uiso 1 1 calc R . . H15B H 0.5686 1.0688 0.0362 0.074 Uiso 1 1 calc R . . C16 C 0.9915(7) 0.5962(8) 0.1423(3) 0.0549(17) Uani 1 1 d . . . H16A H 0.9398 0.5053 0.1371 0.082 Uiso 1 1 calc R . . H16B H 0.9830 0.6168 0.1816 0.082 Uiso 1 1 calc R . . H16C H 1.0973 0.5833 0.1314 0.082 Uiso 1 1 calc R . . C17 C 1.0018(8) 0.9268(8) 0.1122(3) 0.0615(19) Uani 1 1 d . . . H17A H 1.0261 0.9220 0.1518 0.092 Uiso 1 1 calc R . . H17B H 0.9359 1.0142 0.1029 0.092 Uiso 1 1 calc R . . H17C H 1.0940 0.9341 0.0894 0.092 Uiso 1 1 calc R . . C18 C 0.9323(7) 0.7277(9) 0.0229(3) 0.0550(18) Uani 1 1 d . . . H18A H 1.0383 0.7359 0.0123 0.083 Uiso 1 1 calc R . . H18B H 0.8732 0.8039 0.0008 0.083 Uiso 1 1 calc R . . H18C H 0.8998 0.6292 0.0158 0.083 Uiso 1 1 calc R . . C19 C 0.7366(9) 0.1322(10) 0.2848(3) 0.076(2) Uani 1 1 d . . . H19A H 0.7340 0.0398 0.3091 0.114 Uiso 1 1 calc R . . H19B H 0.8349 0.1394 0.2660 0.114 Uiso 1 1 calc R . . H19C H 0.6591 0.1328 0.2569 0.114 Uiso 1 1 calc R . . C20 C 0.7088(6) 0.2615(9) 0.3189(3) 0.0538(17) Uani 1 1 d . . . C21 C 0.7133(7) 0.4073(10) 0.2961(3) 0.060(2) Uani 1 1 d . . . H21 H 0.7406 0.4261 0.2578 0.072 Uiso 1 1 calc R . . C22 C 0.6792(6) 0.5270(9) 0.3275(2) 0.0550(18) Uani 1 1 d . . . H22 H 0.6837 0.6263 0.3113 0.066 Uiso 1 1 calc R . . C23 C 0.6387(6) 0.4962(8) 0.3830(2) 0.0453(15) Uani 1 1 d . . . C24 C 0.6358(7) 0.3535(8) 0.4072(3) 0.0541(17) Uani 1 1 d . . . H24 H 0.6103 0.3352 0.4457 0.065 Uiso 1 1 calc R . . C25 C 0.6702(7) 0.2359(9) 0.3750(3) 0.0556(17) Uani 1 1 d . . . H25 H 0.6674 0.1369 0.3916 0.067 Uiso 1 1 calc R . . C26 C 0.2661(9) 0.5138(9) 0.3628(4) 0.076(2) Uani 1 1 d . . . H26 H 0.3553 0.4540 0.3502 0.091 Uiso 1 1 calc R . . C27 C 0.1805(13) 0.4218(18) 0.3981(5) 0.133(5) Uani 1 1 d . . . H27A H 0.1429 0.3412 0.3777 0.160 Uiso 1 1 calc R . . H27B H 0.2414 0.3763 0.4293 0.160 Uiso 1 1 calc R . . C28 C 0.0633(17) 0.5044(12) 0.4184(4) 0.122(5) Uani 1 1 d U . . H28A H 0.0322 0.4528 0.4546 0.146 Uiso 1 1 calc R . . H28B H -0.0203 0.4980 0.3929 0.146 Uiso 1 1 calc R . . C29 C 0.0732(7) 0.6625(9) 0.4277(3) 0.0597(19) Uani 1 1 d . . . H29A H 0.1085 0.6697 0.4659 0.072 Uiso 1 1 calc R . . H29B H -0.0282 0.7102 0.4255 0.072 Uiso 1 1 calc R . . C30 C 0.1789(6) 0.7502(8) 0.3857(2) 0.0496(16) Uani 1 1 d . . . C31 C 0.1147(9) 0.7381(14) 0.3267(3) 0.095(3) Uani 1 1 d U . . C32 C 0.1739(13) 0.5715(14) 0.3088(3) 0.121(5) Uani 1 1 d U . . H32A H 0.0896 0.5075 0.3034 0.145 Uiso 1 1 calc R . . H32B H 0.2387 0.5788 0.2747 0.145 Uiso 1 1 calc R . . C33 C 0.0031(18) 0.8051(18) 0.3075(5) 0.158(6) Uani 1 1 d . . . H33A H -0.0531 0.8719 0.3291 0.190 Uiso 1 1 calc R . . H33B H -0.0270 0.7901 0.2710 0.190 Uiso 1 1 calc R . . C34 C 0.3437(9) 1.0275(9) 0.3457(3) 0.073(2) Uani 1 1 d . . . H34A H 0.2978 1.0248 0.3094 0.109 Uiso 1 1 calc R . . H34B H 0.4390 0.9700 0.3460 0.109 Uiso 1 1 calc R . . H34C H 0.3615 1.1307 0.3522 0.109 Uiso 1 1 calc R . . C35 C 0.0344(10) 1.0575(12) 0.4019(4) 0.092(3) Uani 1 1 d . . . H35A H 0.0015 1.0794 0.3635 0.138 Uiso 1 1 calc R . . H35B H 0.0482 1.1507 0.4186 0.138 Uiso 1 1 calc R . . H35C H -0.0414 1.0006 0.4236 0.138 Uiso 1 1 calc R . . C36 C 0.2981(8) 0.9558(9) 0.4714(3) 0.0609(19) Uani 1 1 d . . . H36A H 0.2912 1.0586 0.4814 0.091 Uiso 1 1 calc R . . H36B H 0.4032 0.9212 0.4702 0.091 Uiso 1 1 calc R . . H36C H 0.2430 0.8927 0.4994 0.091 Uiso 1 1 calc R . . N1 N 0.6231(5) 0.5803(5) 0.06972(17) 0.0335(10) Uani 1 1 d . . . H1 H 0.6221 0.6366 0.0380 0.040 Uiso 1 1 calc R . . N2 N 0.6130(5) 0.6395(5) 0.12308(17) 0.0329(10) Uani 1 1 d . . . N3 N 0.3991(5) 0.6373(6) 0.43048(18) 0.0482(13) Uani 1 1 d . . . H3A H 0.3542 0.6243 0.4634 0.058 Uiso 1 1 calc R . . N4 N 0.3191(5) 0.6540(6) 0.38012(17) 0.0414(12) Uani 1 1 d . . . O1 O 0.7686(4) 0.3475(5) 0.10151(17) 0.0456(10) Uani 1 1 d . . . O2 O 0.6208(4) 0.3660(4) 0.01594(14) 0.0363(9) Uani 1 1 d . . . O3 O 0.6319(4) 0.6114(5) 0.47892(15) 0.0508(11) Uani 1 1 d . . . O4 O 0.6194(5) 0.7812(5) 0.39250(18) 0.0555(12) Uani 1 1 d . . . Si1 Si 0.90468(17) 0.75478(18) 0.09812(6) 0.0365(4) Uani 1 1 d . . . Si2 Si 0.2160(2) 0.9460(2) 0.40169(7) 0.0549(6) Uani 1 1 d . . . S1 S 0.63694(14) 0.39732(15) 0.07288(5) 0.0335(4) Uani 1 1 d . . . S2 S 0.58087(16) 0.6438(2) 0.42277(6) 0.0464(4) 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 0.064(4) 0.053(4) 0.042(3) -0.001(3) 0.011(3) -0.017(3) C2 0.046(3) 0.031(3) 0.042(3) 0.000(2) 0.007(2) -0.008(3) C3 0.063(4) 0.056(4) 0.034(3) 0.011(3) -0.005(3) -0.013(3) C4 0.045(4) 0.056(4) 0.043(3) 0.015(3) -0.011(3) -0.010(3) C5 0.036(3) 0.026(3) 0.035(3) -0.0019(19) -0.001(2) -0.001(2) C6 0.033(3) 0.028(3) 0.036(3) -0.0042(19) -0.001(2) -0.008(2) C7 0.040(3) 0.036(3) 0.036(3) -0.004(2) 0.002(2) -0.009(2) C8 0.037(3) 0.044(4) 0.049(3) -0.016(2) 0.008(2) -0.008(3) C9 0.093(6) 0.064(5) 0.044(4) -0.015(3) 0.018(3) -0.003(4) C10 0.075(5) 0.077(6) 0.050(4) -0.019(3) 0.008(3) 0.004(4) C11 0.057(4) 0.036(4) 0.044(3) -0.006(2) 0.001(3) 0.003(3) C12 0.038(3) 0.025(3) 0.035(3) -0.0067(19) -0.003(2) -0.004(2) C13 0.048(3) 0.031(3) 0.040(3) -0.009(2) -0.009(2) 0.000(3) C14 0.055(4) 0.072(5) 0.048(3) -0.020(3) -0.013(3) 0.028(4) C15 0.072(5) 0.051(5) 0.062(4) -0.004(3) -0.011(3) 0.011(4) C16 0.039(4) 0.048(4) 0.080(5) -0.011(3) -0.020(3) -0.001(3) C17 0.048(4) 0.052(5) 0.089(5) -0.022(4) -0.004(3) -0.020(3) C18 0.037(3) 0.079(5) 0.053(4) -0.021(3) 0.012(3) -0.022(3) C19 0.056(5) 0.106(7) 0.068(5) -0.026(4) -0.002(4) 0.010(4) C20 0.021(3) 0.080(5) 0.061(4) -0.012(3) -0.006(2) 0.006(3) C21 0.036(4) 0.102(6) 0.045(3) -0.013(4) -0.003(3) -0.010(4) C22 0.033(3) 0.091(6) 0.039(3) 0.007(3) -0.008(2) -0.007(3) C23 0.023(3) 0.069(5) 0.042(3) 0.002(3) -0.006(2) 0.001(3) C24 0.036(3) 0.076(5) 0.047(3) 0.009(3) -0.002(2) 0.013(3) C25 0.035(3) 0.070(5) 0.060(4) -0.001(3) -0.004(3) 0.015(3) C26 0.054(5) 0.052(5) 0.123(7) 0.004(4) -0.033(5) -0.008(4) C27 0.083(8) 0.194(15) 0.116(9) 0.046(9) -0.049(7) -0.034(9) C28 0.196(13) 0.095(8) 0.062(5) 0.016(5) 0.036(7) 0.068(8) C29 0.033(3) 0.093(6) 0.055(4) -0.009(3) -0.014(3) -0.007(3) C30 0.027(3) 0.083(5) 0.038(3) -0.007(3) -0.008(2) 0.015(3) C31 0.046(4) 0.191(11) 0.045(4) -0.014(5) -0.018(3) 0.050(5) C32 0.158(10) 0.174(12) 0.045(4) -0.051(5) 0.028(5) -0.102(9) C33 0.180(15) 0.186(15) 0.100(9) 0.026(9) -0.019(9) 0.029(12) C34 0.081(6) 0.072(5) 0.061(4) 0.012(4) 0.012(4) 0.013(4) C35 0.075(6) 0.111(8) 0.088(6) -0.015(5) -0.019(5) 0.047(6) C36 0.050(4) 0.081(5) 0.051(4) 0.000(3) -0.009(3) 0.011(4) N1 0.038(3) 0.027(3) 0.035(2) -0.0026(17) 0.0075(17) -0.0065(19) N2 0.030(2) 0.034(3) 0.035(2) -0.0064(17) 0.0010(17) -0.0004(19) N3 0.026(2) 0.084(4) 0.032(2) 0.003(2) -0.0058(18) 0.004(2) N4 0.030(2) 0.061(3) 0.032(2) 0.001(2) -0.0058(17) 0.005(2) O1 0.033(2) 0.038(3) 0.067(3) -0.0099(18) -0.0082(18) 0.0031(18) O2 0.038(2) 0.029(2) 0.042(2) -0.0101(15) 0.0072(15) -0.0031(16) O3 0.033(2) 0.080(3) 0.038(2) 0.0009(19) -0.0097(16) 0.004(2) O4 0.039(2) 0.072(3) 0.054(2) 0.010(2) -0.0086(18) -0.004(2) Si1 0.0287(8) 0.0386(10) 0.0434(8) -0.0083(6) -0.0031(6) -0.0054(7) Si2 0.0470(11) 0.0758(14) 0.0378(9) 0.0054(8) -0.0004(7) 0.0229(9) S1 0.0286(7) 0.0279(8) 0.0444(7) -0.0061(5) 0.0011(5) -0.0021(6) S2 0.0277(8) 0.0698(12) 0.0399(7) 0.0054(7) -0.0068(5) 0.0022(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.508(8) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C2 C7 1.395(7) . ? C2 C3 1.392(9) . ? C3 C4 1.377(9) . ? C3 H3 0.9500 . ? C4 C5 1.389(7) . ? C4 H4 0.9500 . ? C5 C6 1.389(7) . ? C5 S1 1.750(5) . ? C6 C7 1.384(7) . ? C6 H6 0.9500 . ? C7 H7 0.9500 . ? C8 N2 1.489(7) . ? C8 C9 1.500(8) . ? C8 C14 1.563(9) . ? C8 H8 1.0000 . ? C9 C10 1.467(11) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 C11 1.503(9) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 C12 1.556(7) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 N2 1.505(7) . ? C12 C13 1.519(7) . ? C12 Si1 1.920(6) . ? C13 C15 1.275(9) . ? C13 C14 1.579(9) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C15 H15A 0.9500 . ? C15 H15B 0.9500 . ? C16 Si1 1.866(7) . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C17 Si1 1.876(7) . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C18 Si1 1.857(6) . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C19 C20 1.495(10) . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? C20 C25 1.387(9) . ? C20 C21 1.386(10) . ? C21 C22 1.392(10) . ? C21 H21 0.9500 . ? C22 C23 1.381(8) . ? C22 H22 0.9500 . ? C23 C24 1.371(9) . ? C23 S2 1.762(7) . ? C24 C25 1.389(10) . ? C24 H24 0.9500 . ? C25 H25 0.9500 . ? C26 C27 1.378(13) . ? C26 N4 1.470(9) . ? C26 C32 1.598(13) . ? C26 H26 1.0000 . ? C27 C28 1.365(15) . ? C27 H27A 0.9900 . ? C27 H27B 0.9900 . ? C28 C29 1.474(13) . ? C28 H28A 0.9900 . ? C28 H28B 0.9900 . ? C29 C30 1.554(9) . ? C29 H29A 0.9900 . ? C29 H29B 0.9900 . ? C30 N4 1.507(7) . ? C30 C31 1.562(9) . ? C30 Si2 1.890(8) . ? C31 C33 1.228(14) . ? C31 C32 1.664(16) . ? C32 H32A 0.9900 . ? C32 H32B 0.9900 . ? C33 H33A 0.9500 . ? C33 H33B 0.9500 . ? C34 Si2 1.865(7) . ? C34 H34A 0.9800 . ? C34 H34B 0.9800 . ? C34 H34C 0.9800 . ? C35 Si2 1.877(8) . ? C35 H35A 0.9800 . ? C35 H35B 0.9800 . ? C35 H35C 0.9800 . ? C36 Si2 1.864(7) . ? C36 H36A 0.9800 . ? C36 H36B 0.9800 . ? C36 H36C 0.9800 . ? N1 N2 1.433(6) . ? N1 S1 1.650(5) . ? N1 H1 0.8800 . ? N3 N4 1.421(6) . ? N3 S2 1.636(5) . ? N3 H3A 0.8800 . ? O1 S1 1.421(4) . ? O2 S1 1.436(4) . ? O3 S2 1.442(4) . ? O4 S2 1.435(5) . ? 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 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? C7 C2 C3 118.5(5) . . ? C7 C2 C1 120.0(5) . . ? C3 C2 C1 121.5(5) . . ? C4 C3 C2 121.0(5) . . ? C4 C3 H3 119.5 . . ? C2 C3 H3 119.5 . . ? C3 C4 C5 119.9(6) . . ? C3 C4 H4 120.0 . . ? C5 C4 H4 120.0 . . ? C4 C5 C6 119.9(5) . . ? C4 C5 S1 119.3(4) . . ? C6 C5 S1 120.5(4) . . ? C7 C6 C5 119.8(5) . . ? C7 C6 H6 120.1 . . ? C5 C6 H6 120.1 . . ? C6 C7 C2 120.8(5) . . ? C6 C7 H7 119.6 . . ? C2 C7 H7 119.6 . . ? N2 C8 C9 108.5(5) . . ? N2 C8 C14 103.4(5) . . ? C9 C8 C14 110.9(5) . . ? N2 C8 H8 111.3 . . ? C9 C8 H8 111.3 . . ? C14 C8 H8 111.3 . . ? C10 C9 C8 113.1(6) . . ? C10 C9 H9A 108.9 . . ? C8 C9 H9A 109.0 . . ? C10 C9 H9B 109.0 . . ? C8 C9 H9B 109.0 . . ? H9A C9 H9B 107.8 . . ? C9 C10 C11 109.2(6) . . ? C9 C10 H10A 109.8 . . ? C11 C10 H10A 109.8 . . ? C9 C10 H10B 109.9 . . ? C11 C10 H10B 109.8 . . ? H10A C10 H10B 108.3 . . ? C10 C11 C12 115.7(5) . . ? C10 C11 H11A 108.3 . . ? C12 C11 H11A 108.3 . . ? C10 C11 H11B 108.4 . . ? C12 C11 H11B 108.4 . . ? H11A C11 H11B 107.4 . . ? N2 C12 C13 104.1(4) . . ? N2 C12 C11 103.9(4) . . ? C13 C12 C11 109.3(4) . . ? N2 C12 Si1 114.0(3) . . ? C13 C12 Si1 116.1(4) . . ? C11 C12 Si1 108.7(4) . . ? C15 C13 C12 130.5(6) . . ? C15 C13 C14 124.9(6) . . ? C12 C13 C14 104.7(5) . . ? C8 C14 C13 103.8(5) . . ? C8 C14 H14A 111.0 . . ? C13 C14 H14A 111.0 . . ? C8 C14 H14B 111.0 . . ? C13 C14 H14B 111.0 . . ? H14A C14 H14B 109.0 . . ? C13 C15 H15A 120.0 . . ? C13 C15 H15B 120.0 . . ? H15A C15 H15B 120.0 . . ? Si1 C16 H16A 109.5 . . ? Si1 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? Si1 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? Si1 C17 H17A 109.5 . . ? Si1 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? Si1 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 . . ? C20 C19 H19A 109.5 . . ? C20 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C20 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C25 C20 C21 118.2(7) . . ? C25 C20 C19 119.2(7) . . ? C21 C20 C19 122.5(7) . . ? C22 C21 C20 122.2(6) . . ? C22 C21 H21 118.9 . . ? C20 C21 H21 118.9 . . ? C23 C22 C21 117.6(7) . . ? C23 C22 H22 121.2 . . ? C21 C22 H22 121.2 . . ? C24 C23 C22 121.8(6) . . ? C24 C23 S2 119.1(5) . . ? C22 C23 S2 119.0(5) . . ? C23 C24 C25 119.5(6) . . ? C23 C24 H24 120.2 . . ? C25 C24 H24 120.2 . . ? C20 C25 C24 120.7(7) . . ? C20 C25 H25 119.7 . . ? C24 C25 H25 119.7 . . ? C27 C26 N4 121.5(10) . . ? C27 C26 C32 110.0(7) . . ? N4 C26 C32 101.3(6) . . ? C27 C26 H26 107.8 . . ? N4 C26 H26 107.8 . . ? C32 C26 H26 107.8 . . ? C28 C27 C26 108.3(13) . . ? C28 C27 H27A 110.0 . . ? C26 C27 H27A 110.0 . . ? C28 C27 H27B 110.0 . . ? C26 C27 H27B 110.0 . . ? H27A C27 H27B 108.4 . . ? C27 C28 C29 122.9(13) . . ? C27 C28 H28A 106.6 . . ? C29 C28 H28A 106.6 . . ? C27 C28 H28B 106.6 . . ? C29 C28 H28B 106.6 . . ? H28A C28 H28B 106.6 . . ? C28 C29 C30 114.5(7) . . ? C28 C29 H29A 108.6 . . ? C30 C29 H29A 108.6 . . ? C28 C29 H29B 108.7 . . ? C30 C29 H29B 108.6 . . ? H29A C29 H29B 107.6 . . ? N4 C30 C29 106.5(5) . . ? N4 C30 C31 98.9(5) . . ? C29 C30 C31 106.0(6) . . ? N4 C30 Si2 113.4(4) . . ? C29 C30 Si2 116.0(4) . . ? C31 C30 Si2 114.4(6) . . ? C33 C31 C30 126.3(10) . . ? C33 C31 C32 123.3(11) . . ? C30 C31 C32 105.2(6) . . ? C26 C32 C31 99.9(5) . . ? C26 C32 H32A 111.8 . . ? C31 C32 H32A 111.8 . . ? C26 C32 H32B 111.8 . . ? C31 C32 H32B 111.8 . . ? H32A C32 H32B 109.5 . . ? C31 C33 H33A 120.0 . . ? C31 C33 H33B 120.0 . . ? H33A C33 H33B 120.0 . . ? Si2 C34 H34A 109.5 . . ? Si2 C34 H34B 109.5 . . ? H34A C34 H34B 109.5 . . ? Si2 C34 H34C 109.5 . . ? H34A C34 H34C 109.5 . . ? H34B C34 H34C 109.5 . . ? Si2 C35 H35A 109.5 . . ? Si2 C35 H35B 109.5 . . ? H35A C35 H35B 109.5 . . ? Si2 C35 H35C 109.5 . . ? H35A C35 H35C 109.5 . . ? H35B C35 H35C 109.5 . . ? Si2 C36 H36A 109.5 . . ? Si2 C36 H36B 109.5 . . ? H36A C36 H36B 109.5 . . ? Si2 C36 H36C 109.5 . . ? H36A C36 H36C 109.5 . . ? H36B C36 H36C 109.5 . . ? N2 N1 S1 114.2(3) . . ? N2 N1 H1 122.9 . . ? S1 N1 H1 122.9 . . ? N1 N2 C8 109.9(4) . . ? N1 N2 C12 110.1(4) . . ? C8 N2 C12 102.7(4) . . ? N4 N3 S2 115.2(3) . . ? N4 N3 H3A 122.4 . . ? S2 N3 H3A 122.4 . . ? N3 N4 C26 113.9(5) . . ? N3 N4 C30 111.6(4) . . ? C26 N4 C30 104.3(5) . . ? C18 Si1 C16 110.9(3) . . ? C18 Si1 C17 107.9(3) . . ? C16 Si1 C17 107.6(3) . . ? C18 Si1 C12 114.0(3) . . ? C16 Si1 C12 108.3(3) . . ? C17 Si1 C12 107.8(3) . . ? C36 Si2 C34 110.3(4) . . ? C36 Si2 C35 106.8(4) . . ? C34 Si2 C35 109.6(4) . . ? C36 Si2 C30 113.3(3) . . ? C34 Si2 C30 107.9(3) . . ? C35 Si2 C30 109.0(4) . . ? O1 S1 O2 119.8(2) . . ? O1 S1 N1 109.0(2) . . ? O2 S1 N1 103.3(2) . . ? O1 S1 C5 108.0(2) . . ? O2 S1 C5 109.2(2) . . ? N1 S1 C5 106.9(2) . . ? O4 S2 O3 119.0(3) . . ? O4 S2 N3 109.8(3) . . ? O3 S2 N3 103.0(2) . . ? O4 S2 C23 108.8(3) . . ? O3 S2 C23 108.9(3) . . ? N3 S2 C23 106.4(3) . . ? _diffrn_measured_fraction_theta_max 0.733 _diffrn_reflns_theta_full 27.45 _diffrn_measured_fraction_theta_full 0.733 _refine_diff_density_max 1.846 _refine_diff_density_min -0.502 _refine_diff_density_rms 0.085 data_12c _database_code_CSD 212878 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H22 N2 O2 S' _chemical_formula_weight 306.42 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 12.8588(2) _cell_length_b 10.7382(2) _cell_length_c 23.1122(4) _cell_angle_alpha 90.00 _cell_angle_beta 93.811(3) _cell_angle_gamma 90.00 _cell_volume 3184.28(9) _cell_formula_units_Z 8 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 7530 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.49 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.278 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1312 _exptl_absorpt_coefficient_mu 0.210 _exptl_absorpt_correction_type multiscan _exptl_absorpt_correction_T_min 0.9593 _exptl_absorpt_correction_T_max 0.9593 _exptl_absorpt_process_details 'SORTAV (Blessing, 1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Nonius FR591 rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_decay_% negligible _diffrn_reflns_number 8166 _diffrn_reflns_av_R_equivalents 0.0554 _diffrn_reflns_av_sigmaI/netI 0.0544 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 2.98 _diffrn_reflns_theta_max 25.03 _reflns_number_total 2784 _reflns_number_gt 2306 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'DENZO (Otwinowsi & Minor, 1997) & COLLECT (Hooft, 1998)' _computing_cell_refinement 'DENZO & COLLECT' _computing_data_reduction 'DENZO & COLLECT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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^ > 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^)+(0.0493P)^2^+0.7825P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment riding _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0023(5) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2784 _refine_ls_number_parameters 279 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0492 _refine_ls_R_factor_gt 0.0376 _refine_ls_wR_factor_ref 0.0986 _refine_ls_wR_factor_gt 0.0928 _refine_ls_goodness_of_fit_ref 1.055 _refine_ls_restrained_S_all 1.055 _refine_ls_shift/su_max 0.004 _refine_ls_shift/su_mean 0.001 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 0.43208(3) 0.01335(4) 0.341113(16) 0.01980(18) Uani 1 1 d . . . N1 N 0.53206(11) -0.06940(15) 0.32441(6) 0.0192(4) Uani 1 1 d . . . N2 N 0.58695(10) -0.13013(14) 0.37203(5) 0.0194(4) Uani 1 1 d . . . O1 O 0.36349(9) -0.06334(12) 0.37163(5) 0.0256(3) Uani 1 1 d . . . O2 O 0.39592(9) 0.06968(13) 0.28698(5) 0.0263(3) Uani 1 1 d . . . C1 C 0.6453(2) 0.3823(3) 0.50715(11) 0.0460(6) Uani 1 1 d . . . C2 C 0.58623(15) 0.29496(19) 0.46560(8) 0.0291(5) Uani 1 1 d . . . C3 C 0.52525(14) 0.20004(18) 0.48614(8) 0.0256(4) Uani 1 1 d . . . C4 C 0.47310(14) 0.11720(18) 0.44827(7) 0.0223(4) Uani 1 1 d . . . C5 C 0.48182(13) 0.12978(17) 0.38905(7) 0.0199(4) Uani 1 1 d . . . C6 C 0.54001(15) 0.2262(2) 0.36772(8) 0.0313(5) Uani 1 1 d . . . C7 C 0.59203(17) 0.3075(2) 0.40585(8) 0.0360(5) Uani 1 1 d . . . C8 C 0.68679(13) -0.06908(18) 0.39223(7) 0.0214(4) Uani 1 1 d . . . C9 C 0.72957(15) -0.16644(19) 0.43597(7) 0.0249(4) Uani 1 1 d . . . C10 C 0.69300(15) -0.29103(19) 0.40801(8) 0.0261(4) Uani 1 1 d . . . C11 C 0.62103(13) -0.25655(17) 0.35427(7) 0.0216(4) Uani 1 1 d . . . C12 C 0.68281(14) -0.24522(19) 0.29947(7) 0.0253(4) Uani 1 1 d . . . C13 C 0.75725(14) -0.13684(19) 0.30088(7) 0.0265(5) Uani 1 1 d . . . C14 C 0.75796(15) -0.05402(19) 0.34356(7) 0.0255(4) Uani 1 1 d . . . C15 C 0.82754(18) -0.1270(3) 0.25181(9) 0.0392(6) Uani 1 1 d . . . C16 C 0.52886(16) -0.3424(2) 0.34442(9) 0.0296(5) Uani 1 1 d . . . H1A H 0.702(2) 0.410(3) 0.4907(10) 0.057(8) Uiso 1 1 d . . . H1B H 0.598(2) 0.447(3) 0.5213(11) 0.076(9) Uiso 1 1 d . . . H1C H 0.670(2) 0.339(3) 0.5451(12) 0.071(8) Uiso 1 1 d . . . H1N H 0.5671(17) -0.031(2) 0.3012(9) 0.034(6) Uiso 1 1 d . . . H3 H 0.5172(14) 0.1885(19) 0.5252(9) 0.029(5) Uiso 1 1 d . . . H4 H 0.4309(14) 0.0489(19) 0.4624(7) 0.020(5) Uiso 1 1 d . . . H6 H 0.5465(15) 0.234(2) 0.3280(9) 0.034(5) Uiso 1 1 d . . . H7 H 0.6374(19) 0.369(3) 0.3920(10) 0.057(7) Uiso 1 1 d . . . H8 H 0.6719(13) 0.0119(18) 0.4095(7) 0.015(4) Uiso 1 1 d . . . H9A H 0.8070(14) -0.1644(17) 0.4408(7) 0.019(4) Uiso 1 1 d . . . H9B H 0.7000(14) -0.1529(18) 0.4724(9) 0.026(5) Uiso 1 1 d . . . H10A H 0.6525(16) -0.339(2) 0.4354(9) 0.037(6) Uiso 1 1 d . . . H10B H 0.7531(15) -0.3438(19) 0.3981(7) 0.027(5) Uiso 1 1 d . . . H12A H 0.7199(16) -0.321(2) 0.2924(8) 0.041(6) Uiso 1 1 d . . . H12B H 0.6356(15) -0.235(2) 0.2651(9) 0.034(5) Uiso 1 1 d . . . H14 H 0.8069(15) 0.0101(19) 0.3421(8) 0.025(5) Uiso 1 1 d . . . H15A H 0.7876(17) -0.127(2) 0.2143(10) 0.043(6) Uiso 1 1 d . . . H15B H 0.875(2) -0.201(3) 0.2526(10) 0.061(8) Uiso 1 1 d . . . H15C H 0.871(2) -0.046(3) 0.2556(9) 0.055(7) Uiso 1 1 d . . . H16A H 0.5542(17) -0.423(2) 0.3326(8) 0.040(6) Uiso 1 1 d . . . H16B H 0.4803(16) -0.309(2) 0.3109(9) 0.039(6) Uiso 1 1 d . . . H16C H 0.4912(15) -0.3485(19) 0.3791(9) 0.031(5) Uiso 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 S1 0.0186(3) 0.0233(3) 0.0172(2) -0.00222(17) -0.00128(16) 0.00629(19) N1 0.0205(8) 0.0236(9) 0.0133(7) 0.0018(6) -0.0002(6) 0.0067(7) N2 0.0202(8) 0.0228(9) 0.0146(7) 0.0004(6) -0.0042(5) 0.0073(6) O1 0.0216(7) 0.0282(8) 0.0272(7) -0.0027(5) 0.0035(5) -0.0001(6) O2 0.0283(7) 0.0303(8) 0.0193(6) -0.0013(5) -0.0061(5) 0.0130(6) C1 0.0549(16) 0.0392(15) 0.0429(13) -0.0106(11) -0.0035(12) -0.0144(13) C2 0.0342(11) 0.0230(11) 0.0297(10) -0.0027(8) -0.0019(8) 0.0011(9) C3 0.0318(10) 0.0277(11) 0.0175(9) -0.0030(8) 0.0020(7) 0.0034(8) C4 0.0229(9) 0.0221(11) 0.0221(9) 0.0007(8) 0.0034(7) 0.0039(8) C5 0.0199(9) 0.0208(10) 0.0188(8) -0.0001(7) 0.0000(6) 0.0073(8) C6 0.0409(12) 0.0332(12) 0.0197(9) 0.0044(8) 0.0023(8) -0.0032(10) C7 0.0459(13) 0.0270(12) 0.0352(11) 0.0056(9) 0.0032(9) -0.0109(10) C8 0.0207(9) 0.0224(11) 0.0205(9) -0.0024(7) -0.0031(7) 0.0026(8) C9 0.0244(10) 0.0320(12) 0.0176(9) 0.0007(8) -0.0037(7) 0.0060(8) C10 0.0278(10) 0.0271(11) 0.0226(9) 0.0032(8) -0.0029(8) 0.0075(9) C11 0.0224(9) 0.0212(10) 0.0206(9) -0.0005(7) -0.0024(7) 0.0077(8) C12 0.0268(10) 0.0288(11) 0.0200(9) -0.0031(8) -0.0013(7) 0.0109(9) C13 0.0214(9) 0.0351(12) 0.0230(9) 0.0081(8) 0.0008(7) 0.0122(9) C14 0.0203(10) 0.0294(11) 0.0264(9) 0.0065(8) -0.0016(7) 0.0024(9) C15 0.0361(12) 0.0526(16) 0.0301(11) 0.0101(10) 0.0114(9) 0.0147(12) C16 0.0320(11) 0.0255(12) 0.0304(11) -0.0003(9) -0.0037(9) 0.0027(9) _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 O1 1.4270(13) . ? S1 O2 1.4388(12) . ? S1 N1 1.6301(15) . ? S1 C5 1.7622(17) . ? N1 N2 1.4254(18) . ? N2 C8 1.489(2) . ? N2 C11 1.492(2) . ? C1 C2 1.510(3) . ? C2 C3 1.389(3) . ? C2 C7 1.394(3) . ? C3 C4 1.389(3) . ? C4 C5 1.387(2) . ? C5 C6 1.387(3) . ? C6 C7 1.381(3) . ? C8 C14 1.505(3) . ? C8 C9 1.531(2) . ? C9 C10 1.545(3) . ? C10 C11 1.544(2) . ? C11 C16 1.507(3) . ? C11 C12 1.544(2) . ? C12 C13 1.506(3) . ? C13 C14 1.328(3) . ? C13 C15 1.500(3) . ? 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 O1 S1 O2 119.85(8) . . ? O1 S1 N1 109.00(8) . . ? O2 S1 N1 103.74(7) . . ? O1 S1 C5 108.01(8) . . ? O2 S1 C5 109.35(8) . . ? N1 S1 C5 106.06(8) . . ? N2 N1 S1 115.11(11) . . ? N1 N2 C8 114.40(14) . . ? N1 N2 C11 110.07(12) . . ? C8 N2 C11 102.94(13) . . ? C3 C2 C7 118.55(17) . . ? C3 C2 C1 120.64(18) . . ? C7 C2 C1 120.80(19) . . ? C4 C3 C2 120.97(16) . . ? C5 C4 C3 119.48(18) . . ? C6 C5 C4 120.28(16) . . ? C6 C5 S1 119.21(13) . . ? C4 C5 S1 120.10(14) . . ? C7 C6 C5 119.66(17) . . ? C6 C7 C2 121.02(19) . . ? N2 C8 C14 111.57(14) . . ? N2 C8 C9 99.84(14) . . ? C14 C8 C9 110.92(15) . . ? C8 C9 C10 103.24(13) . . ? C11 C10 C9 106.16(15) . . ? N2 C11 C16 110.82(15) . . ? N2 C11 C10 99.68(13) . . ? C16 C11 C10 113.47(16) . . ? N2 C11 C12 109.30(15) . . ? C16 C11 C12 111.52(15) . . ? C10 C11 C12 111.42(15) . . ? C13 C12 C11 113.84(15) . . ? C14 C13 C15 122.7(2) . . ? C14 C13 C12 120.44(17) . . ? C15 C13 C12 116.89(18) . . ? C13 C14 C8 120.58(19) . . ? 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 N1 H1N O2 0.83(2) 2.38(2) 3.167(2) 157.4(19) 2_655 _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 25.03 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.242 _refine_diff_density_min -0.371 _refine_diff_density_rms 0.050 data_13c _database_code_CSD 212879 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C19 H30 N2 O2 S Si' _chemical_formula_weight 378.60 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 14.8295(3) _cell_length_b 11.9683(2) _cell_length_c 12.0257(2) _cell_angle_alpha 90.00 _cell_angle_beta 105.1330(10) _cell_angle_gamma 90.00 _cell_volume 2060.35(6) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 17171 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.221 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 816 _exptl_absorpt_coefficient_mu 0.230 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9343 _exptl_absorpt_correction_T_max 0.9886 _exptl_absorpt_process_details 'SORTAV (Blessing, 1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Nonius FR591 rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method '\f & \w scans' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_decay_% negligible _diffrn_reflns_number 26079 _diffrn_reflns_av_R_equivalents 0.0644 _diffrn_reflns_av_sigmaI/netI 0.0424 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.05 _diffrn_reflns_theta_max 27.47 _reflns_number_total 4716 _reflns_number_gt 3954 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, 1998)' _computing_cell_refinement 'DENZO & COLLECT' _computing_data_reduction 'DENZO & COLLECT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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^ > 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^)+(0.0479P)^2^+1.0778P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment riding _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0068(12) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 4716 _refine_ls_number_parameters 236 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0525 _refine_ls_R_factor_gt 0.0417 _refine_ls_wR_factor_ref 0.1051 _refine_ls_wR_factor_gt 0.0994 _refine_ls_goodness_of_fit_ref 1.017 _refine_ls_restrained_S_all 1.017 _refine_ls_shift/su_max 0.005 _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 0.19228(14) 0.55377(16) 0.15897(18) 0.0342(4) Uani 1 1 d . . . H1A H 0.2505 0.5474 0.1352 0.051 Uiso 1 1 calc R . . H1B H 0.2055 0.5870 0.2360 0.051 Uiso 1 1 calc R . . H1C H 0.1482 0.6013 0.1042 0.051 Uiso 1 1 calc R . . C2 C 0.15034(11) 0.43949(14) 0.16127(15) 0.0247(4) Uani 1 1 d . . . C3 C 0.16005(11) 0.38409(14) 0.26553(14) 0.0249(4) Uani 1 1 d . . . H3 H 0.1944 0.4184 0.3350 0.030 Uiso 1 1 calc R . . C4 C 0.12050(11) 0.27971(14) 0.26978(14) 0.0225(3) Uani 1 1 d . . . H4 H 0.1282 0.2424 0.3414 0.027 Uiso 1 1 calc R . . C5 C 0.06961(10) 0.23035(14) 0.16838(13) 0.0195(3) Uani 1 1 d . . . C6 C 0.05893(11) 0.28416(15) 0.06308(14) 0.0236(3) Uani 1 1 d . . . H6 H 0.0244 0.2499 -0.0062 0.028 Uiso 1 1 calc R . . C7 C 0.09932(12) 0.38847(15) 0.06042(15) 0.0263(4) Uani 1 1 d . . . H7 H 0.0920 0.4255 -0.0112 0.032 Uiso 1 1 calc R . . C8 C 0.22265(11) -0.09887(13) 0.27589(14) 0.0216(3) Uani 1 1 d . . . C9 C 0.25263(11) -0.14638(14) 0.17141(15) 0.0242(4) Uani 1 1 d . . . H9A H 0.3067 -0.1972 0.1968 0.029 Uiso 1 1 calc R . . H9B H 0.2006 -0.1875 0.1191 0.029 Uiso 1 1 calc R . . C10 C 0.27868(10) -0.04367(14) 0.11241(14) 0.0208(3) Uani 1 1 d . . . C11 C 0.31262(11) -0.04133(16) 0.02078(14) 0.0264(4) Uani 1 1 d . . . H11A H 0.3230 -0.1092 -0.0150 0.032 Uiso 1 1 calc R . . H11B H 0.3265 0.0282 -0.0091 0.032 Uiso 1 1 calc R . . C12 C 0.25563(10) 0.05762(13) 0.17698(13) 0.0179(3) Uani 1 1 d . . . H12 H 0.2295 0.1199 0.1227 0.021 Uiso 1 1 calc R . . C13 C 0.15109(12) -0.16893(15) 0.31424(17) 0.0291(4) Uani 1 1 d . . . H13A H 0.1274 -0.1270 0.3707 0.044 Uiso 1 1 calc R . . H13B H 0.1804 -0.2383 0.3494 0.044 Uiso 1 1 calc R . . H13C H 0.0992 -0.1868 0.2474 0.044 Uiso 1 1 calc R . . C14 C 0.30729(11) -0.07534(15) 0.37843(14) 0.0250(4) Uani 1 1 d . . . H14A H 0.2856 -0.0363 0.4393 0.030 Uiso 1 1 calc R . . H14B H 0.3351 -0.1474 0.4107 0.030 Uiso 1 1 calc R . . C15 C 0.38298(11) -0.00413(15) 0.34624(14) 0.0234(3) Uani 1 1 d . . . H15A H 0.4170 -0.0503 0.3021 0.028 Uiso 1 1 calc R . . H15B H 0.4284 0.0217 0.4173 0.028 Uiso 1 1 calc R . . C16 C 0.33952(10) 0.09764(13) 0.27352(13) 0.0191(3) Uani 1 1 d . . . H16 H 0.3122 0.1444 0.3255 0.023 Uiso 1 1 calc R . . C17 C 0.48378(14) 0.27471(19) 0.36105(17) 0.0391(5) Uani 1 1 d . . . H17A H 0.5310 0.3243 0.3440 0.059 Uiso 1 1 calc R . . H17B H 0.5135 0.2244 0.4243 0.059 Uiso 1 1 calc R . . H17C H 0.4361 0.3195 0.3835 0.059 Uiso 1 1 calc R . . C18 C 0.52141(12) 0.11028(17) 0.18612(17) 0.0320(4) Uani 1 1 d . . . H18A H 0.4930 0.0638 0.1190 0.048 Uiso 1 1 calc R . . H18B H 0.5545 0.0625 0.2500 0.048 Uiso 1 1 calc R . . H18C H 0.5657 0.1625 0.1663 0.048 Uiso 1 1 calc R . . C19 C 0.36726(13) 0.28710(16) 0.11188(17) 0.0328(4) Uani 1 1 d . . . H19A H 0.4118 0.3425 0.0982 0.049 Uiso 1 1 calc R . . H19B H 0.3162 0.3253 0.1341 0.049 Uiso 1 1 calc R . . H19C H 0.3420 0.2440 0.0413 0.049 Uiso 1 1 calc R . . N1 N 0.09500(9) 0.00444(12) 0.15477(12) 0.0200(3) Uani 1 1 d . . . N2 N 0.18478(8) 0.01481(11) 0.23485(11) 0.0182(3) Uani 1 1 d . . . O1 O -0.05992(7) 0.08447(10) 0.07705(10) 0.0259(3) Uani 1 1 d . . . O2 O 0.00892(8) 0.08465(10) 0.28851(10) 0.0248(3) Uani 1 1 d . . . Si1 Si 0.42799(3) 0.19064(4) 0.23021(4) 0.02230(13) Uani 1 1 d . . . S1 S 0.02003(2) 0.09757(3) 0.17471(3) 0.01950(12) Uani 1 1 d . . . H1N H 0.0918(14) -0.0101(17) 0.0845(18) 0.029(5) Uiso 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 0.0367(10) 0.0255(9) 0.0451(11) -0.0016(8) 0.0190(9) -0.0017(8) C2 0.0219(8) 0.0227(8) 0.0319(9) -0.0032(7) 0.0113(7) 0.0035(6) C3 0.0233(8) 0.0257(9) 0.0250(8) -0.0076(7) 0.0051(7) -0.0033(7) C4 0.0212(8) 0.0250(8) 0.0211(8) -0.0026(7) 0.0054(6) 0.0012(6) C5 0.0144(7) 0.0222(8) 0.0220(8) -0.0034(6) 0.0047(6) 0.0031(6) C6 0.0211(8) 0.0288(9) 0.0197(8) -0.0042(7) 0.0032(6) 0.0025(7) C7 0.0290(9) 0.0275(9) 0.0241(8) 0.0032(7) 0.0099(7) 0.0047(7) C8 0.0190(7) 0.0187(8) 0.0280(8) 0.0021(7) 0.0075(6) 0.0004(6) C9 0.0211(8) 0.0195(8) 0.0330(9) -0.0018(7) 0.0087(7) 0.0016(6) C10 0.0125(7) 0.0234(8) 0.0244(8) -0.0013(7) 0.0012(6) 0.0013(6) C11 0.0220(8) 0.0322(9) 0.0240(8) -0.0018(7) 0.0041(6) 0.0030(7) C12 0.0126(7) 0.0190(8) 0.0221(7) 0.0033(6) 0.0047(6) -0.0003(6) C13 0.0263(9) 0.0236(9) 0.0405(10) 0.0019(8) 0.0144(8) -0.0041(7) C14 0.0215(8) 0.0269(9) 0.0261(8) 0.0069(7) 0.0055(7) 0.0009(7) C15 0.0154(7) 0.0296(9) 0.0231(8) 0.0024(7) 0.0013(6) -0.0008(6) C16 0.0142(7) 0.0220(8) 0.0208(8) -0.0018(6) 0.0044(6) -0.0025(6) C17 0.0353(10) 0.0453(12) 0.0383(11) -0.0098(9) 0.0125(8) -0.0217(9) C18 0.0187(8) 0.0372(10) 0.0427(11) 0.0023(8) 0.0126(8) -0.0007(7) C19 0.0285(9) 0.0314(10) 0.0419(10) 0.0073(8) 0.0152(8) 0.0008(7) N1 0.0120(6) 0.0235(7) 0.0237(7) -0.0061(6) 0.0029(5) 0.0000(5) N2 0.0115(6) 0.0188(6) 0.0237(7) 0.0006(5) 0.0034(5) -0.0019(5) O1 0.0122(5) 0.0340(7) 0.0292(6) -0.0100(5) 0.0012(5) 0.0000(5) O2 0.0188(6) 0.0314(7) 0.0261(6) -0.0024(5) 0.0097(5) -0.0023(5) Si1 0.0161(2) 0.0248(2) 0.0271(2) -0.00073(18) 0.00751(18) -0.00408(17) S1 0.01175(19) 0.0237(2) 0.0229(2) -0.00497(15) 0.00426(14) -0.00044(14) _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 C1 C2 1.506(2) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C2 C7 1.392(2) . ? C2 C3 1.392(2) . ? C3 C4 1.387(2) . ? C3 H3 0.9500 . ? C4 C5 1.388(2) . ? C4 H4 0.9500 . ? C5 C6 1.392(2) . ? C5 S1 1.7610(17) . ? C6 C7 1.389(2) . ? C6 H6 0.9500 . ? C7 H7 0.9500 . ? C8 N2 1.505(2) . ? C8 C13 1.516(2) . ? C8 C14 1.539(2) . ? C8 C9 1.546(2) . ? C9 C10 1.519(2) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 C11 1.326(2) . ? C10 C12 1.526(2) . ? C11 H11A 0.9500 . ? C11 H11B 0.9500 . ? C12 N2 1.4941(18) . ? C12 C16 1.540(2) . ? C12 H12 1.0000 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C14 C15 1.537(2) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C15 C16 1.539(2) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 Si1 1.8942(16) . ? C16 H16 1.0000 . ? C17 Si1 1.8689(19) . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C18 Si1 1.8732(18) . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C19 Si1 1.8707(19) . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? N1 N2 1.4304(17) . ? N1 S1 1.6356(14) . ? N1 H1N 0.85(2) . ? O1 S1 1.4431(11) . ? O2 S1 1.4288(12) . ? 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 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? C7 C2 C3 118.73(16) . . ? C7 C2 C1 121.05(16) . . ? C3 C2 C1 120.20(16) . . ? C4 C3 C2 121.13(15) . . ? C4 C3 H3 119.4 . . ? C2 C3 H3 119.4 . . ? C3 C4 C5 119.30(15) . . ? C3 C4 H4 120.3 . . ? C5 C4 H4 120.3 . . ? C4 C5 C6 120.60(15) . . ? C4 C5 S1 118.92(12) . . ? C6 C5 S1 120.47(12) . . ? C7 C6 C5 119.30(15) . . ? C7 C6 H6 120.3 . . ? C5 C6 H6 120.3 . . ? C6 C7 C2 120.93(16) . . ? C6 C7 H7 119.5 . . ? C2 C7 H7 119.5 . . ? N2 C8 C13 111.65(13) . . ? N2 C8 C14 104.70(13) . . ? C13 C8 C14 110.29(14) . . ? N2 C8 C9 103.17(12) . . ? C13 C8 C9 114.61(14) . . ? C14 C8 C9 111.79(13) . . ? C10 C9 C8 104.13(13) . . ? C10 C9 H9A 110.9 . . ? C8 C9 H9A 110.9 . . ? C10 C9 H9B 110.9 . . ? C8 C9 H9B 110.9 . . ? H9A C9 H9B 108.9 . . ? C11 C10 C9 127.11(16) . . ? C11 C10 C12 126.18(16) . . ? C9 C10 C12 106.69(13) . . ? C10 C11 H11A 120.0 . . ? C10 C11 H11B 120.0 . . ? H11A C11 H11B 120.0 . . ? N2 C12 C10 104.05(12) . . ? N2 C12 C16 106.47(12) . . ? C10 C12 C16 112.75(12) . . ? N2 C12 H12 111.1 . . ? C10 C12 H12 111.1 . . ? C16 C12 H12 111.1 . . ? C8 C13 H13A 109.5 . . ? C8 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C8 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C15 C14 C8 113.34(13) . . ? C15 C14 H14A 108.9 . . ? C8 C14 H14A 108.9 . . ? C15 C14 H14B 108.9 . . ? C8 C14 H14B 108.9 . . ? H14A C14 H14B 107.7 . . ? C14 C15 C16 110.90(12) . . ? C14 C15 H15A 109.5 . . ? C16 C15 H15A 109.5 . . ? C14 C15 H15B 109.5 . . ? C16 C15 H15B 109.5 . . ? H15A C15 H15B 108.0 . . ? C15 C16 C12 108.56(13) . . ? C15 C16 Si1 113.82(10) . . ? C12 C16 Si1 117.18(10) . . ? C15 C16 H16 105.4 . . ? C12 C16 H16 105.4 . . ? Si1 C16 H16 105.4 . . ? Si1 C17 H17A 109.5 . . ? Si1 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? Si1 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 . . ? N2 N1 S1 113.01(10) . . ? N2 N1 H1N 119.1(13) . . ? S1 N1 H1N 114.9(14) . . ? N1 N2 C12 111.12(11) . . ? N1 N2 C8 110.14(12) . . ? C12 N2 C8 102.42(11) . . ? C17 Si1 C19 109.13(10) . . ? C17 Si1 C18 108.49(9) . . ? C19 Si1 C18 110.26(9) . . ? C17 Si1 C16 105.72(8) . . ? C19 Si1 C16 109.96(8) . . ? C18 Si1 C16 113.12(8) . . ? O2 S1 O1 119.47(7) . . ? O2 S1 N1 108.63(7) . . ? O1 S1 N1 104.60(7) . . ? O2 S1 C5 107.03(7) . . ? O1 S1 C5 109.05(7) . . ? N1 S1 C5 107.53(7) . . ? 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 C7 C2 C3 C4 0.4(2) . . . . ? C1 C2 C3 C4 178.79(15) . . . . ? C2 C3 C4 C5 -0.7(2) . . . . ? C3 C4 C5 C6 0.7(2) . . . . ? C3 C4 C5 S1 179.78(12) . . . . ? C4 C5 C6 C7 -0.4(2) . . . . ? S1 C5 C6 C7 -179.53(12) . . . . ? C5 C6 C7 C2 0.2(2) . . . . ? C3 C2 C7 C6 -0.2(2) . . . . ? C1 C2 C7 C6 -178.53(16) . . . . ? N2 C8 C9 C10 29.51(15) . . . . ? C13 C8 C9 C10 151.10(14) . . . . ? C14 C8 C9 C10 -82.47(15) . . . . ? C8 C9 C10 C11 176.98(15) . . . . ? C8 C9 C10 C12 -4.61(15) . . . . ? C11 C10 C12 N2 156.24(15) . . . . ? C9 C10 C12 N2 -22.19(15) . . . . ? C11 C10 C12 C16 -88.81(19) . . . . ? C9 C10 C12 C16 92.76(14) . . . . ? N2 C8 C14 C15 -59.57(17) . . . . ? C13 C8 C14 C15 -179.81(14) . . . . ? C9 C8 C14 C15 51.44(19) . . . . ? C8 C14 C15 C16 47.01(19) . . . . ? C14 C15 C16 C12 -47.74(17) . . . . ? C14 C15 C16 Si1 179.81(11) . . . . ? N2 C12 C16 C15 64.93(15) . . . . ? C10 C12 C16 C15 -48.55(16) . . . . ? N2 C12 C16 Si1 -164.43(10) . . . . ? C10 C12 C16 Si1 82.09(15) . . . . ? S1 N1 N2 C12 -109.13(12) . . . . ? S1 N1 N2 C8 138.09(11) . . . . ? C10 C12 N2 N1 -76.82(14) . . . . ? C16 C12 N2 N1 163.86(12) . . . . ? C10 C12 N2 C8 40.76(14) . . . . ? C16 C12 N2 C8 -78.55(14) . . . . ? C13 C8 N2 N1 -48.98(17) . . . . ? C14 C8 N2 N1 -168.31(12) . . . . ? C9 C8 N2 N1 74.59(14) . . . . ? C13 C8 N2 C12 -167.26(13) . . . . ? C14 C8 N2 C12 73.41(14) . . . . ? C9 C8 N2 C12 -43.69(14) . . . . ? C15 C16 Si1 C17 -77.57(14) . . . . ? C12 C16 Si1 C17 154.27(13) . . . . ? C15 C16 Si1 C19 164.76(12) . . . . ? C12 C16 Si1 C19 36.61(14) . . . . ? C15 C16 Si1 C18 41.01(14) . . . . ? C12 C16 Si1 C18 -87.14(13) . . . . ? N2 N1 S1 O2 -59.66(12) . . . . ? N2 N1 S1 O1 171.70(10) . . . . ? N2 N1 S1 C5 55.85(12) . . . . ? C4 C5 S1 O2 23.90(14) . . . . ? C6 C5 S1 O2 -156.97(13) . . . . ? C4 C5 S1 O1 154.46(12) . . . . ? C6 C5 S1 O1 -26.41(15) . . . . ? C4 C5 S1 N1 -92.66(13) . . . . ? C6 C5 S1 N1 86.47(14) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.247 _refine_diff_density_min -0.430 _refine_diff_density_rms 0.056 data_13d _database_code_CSD 212880 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H28 N2 O2 S Si' _chemical_formula_weight 364.57 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 9.4824(2) _cell_length_b 22.6655(6) _cell_length_c 10.0368(3) _cell_angle_alpha 90.00 _cell_angle_beta 116.1400(10) _cell_angle_gamma 90.00 _cell_volume 1936.51(9) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 8192 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.34 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.250 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 784 _exptl_absorpt_coefficient_mu 0.242 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9223 _exptl_absorpt_correction_T_max 0.9762 _exptl_absorpt_process_details 'SORTAV Blessing (1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'NONIUS FR591 rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method '\f & \w scans' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_decay_% negligible _diffrn_reflns_number 12067 _diffrn_reflns_av_R_equivalents 0.0682 _diffrn_reflns_av_sigmaI/netI 0.0607 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_k_max 29 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.99 _diffrn_reflns_theta_max 27.49 _reflns_number_total 4341 _reflns_number_gt 3436 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, 1998)' _computing_cell_refinement 'DENZO & COLLECT' _computing_data_reduction 'DENZO & COLLECT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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^ > 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^)+(0.0820P)^2^+0.3863P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment riding _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0000(17) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 4341 _refine_ls_number_parameters 226 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0647 _refine_ls_R_factor_gt 0.0474 _refine_ls_wR_factor_ref 0.1348 _refine_ls_wR_factor_gt 0.1236 _refine_ls_goodness_of_fit_ref 1.006 _refine_ls_restrained_S_all 1.006 _refine_ls_shift/su_max 0.641 _refine_ls_shift/su_mean 0.004 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 C11 C 0.3395(2) 0.10254(9) 0.8002(2) 0.0266(4) Uani 1 1 d . . . H11A H 0.4110 0.1053 0.9024 0.032 Uiso 1 1 calc R . . H11B H 0.2482 0.0787 0.7698 0.032 Uiso 1 1 calc R . . C1 C -0.2714(3) 0.04432(12) 0.0342(2) 0.0353(5) Uani 1 1 d . . . H1A H -0.3083 0.0674 0.0953 0.053 Uiso 1 1 calc R . . H1B H -0.3012 0.0029 0.0336 0.053 Uiso 1 1 calc R . . H1C H -0.3193 0.0596 -0.0675 0.053 Uiso 1 1 calc R . . C2 C -0.0952(2) 0.04900(10) 0.0975(2) 0.0246(4) Uani 1 1 d . . . C3 C -0.0245(3) 0.10019(9) 0.0789(2) 0.0286(5) Uani 1 1 d . . . H3 H -0.0886 0.1320 0.0229 0.034 Uiso 1 1 calc R . . C4 C 0.1377(3) 0.10572(9) 0.1407(2) 0.0262(4) Uani 1 1 d . . . H4 H 0.1844 0.1406 0.1257 0.031 Uiso 1 1 calc R . . C5 C 0.2308(2) 0.05958(8) 0.2246(2) 0.0187(4) Uani 1 1 d . . . C6 C 0.1640(2) 0.00797(8) 0.2446(2) 0.0212(4) Uani 1 1 d . . . H6 H 0.2284 -0.0235 0.3018 0.025 Uiso 1 1 calc R . . C7 C 0.0015(2) 0.00309(9) 0.1796(2) 0.0239(4) Uani 1 1 d . . . H7 H -0.0449 -0.0325 0.1914 0.029 Uiso 1 1 calc R . . C8 C 0.4704(2) 0.19430(8) 0.5716(2) 0.0207(4) Uani 1 1 d . . . H8 H 0.5695 0.2019 0.5623 0.025 Uiso 1 1 calc R . . C9 C 0.5056(2) 0.17172(9) 0.7283(2) 0.0225(4) Uani 1 1 d . . . H9A H 0.6056 0.1495 0.7725 0.027 Uiso 1 1 calc R . . H9B H 0.5112 0.2048 0.7948 0.027 Uiso 1 1 calc R . . C10 C 0.3671(2) 0.13176(8) 0.7009(2) 0.0197(4) Uani 1 1 d . . . C12 C 0.2658(2) 0.13006(8) 0.5332(2) 0.0178(4) Uani 1 1 d . . . H12 H 0.2196 0.0900 0.4996 0.021 Uiso 1 1 calc R . . C13 C 0.1375(2) 0.17809(8) 0.4800(2) 0.0188(4) Uani 1 1 d . . . H13 H 0.1026 0.1817 0.3706 0.023 Uiso 1 1 calc R . . C14 C 0.2134(2) 0.23795(8) 0.5459(2) 0.0213(4) Uani 1 1 d . . . H14A H 0.1373 0.2700 0.4960 0.026 Uiso 1 1 calc R . . H14B H 0.2388 0.2389 0.6527 0.026 Uiso 1 1 calc R . . C15 C 0.3638(2) 0.24893(8) 0.5277(2) 0.0230(4) Uani 1 1 d . . . H15A H 0.3355 0.2592 0.4231 0.028 Uiso 1 1 calc R . . H15B H 0.4216 0.2827 0.5906 0.028 Uiso 1 1 calc R . . C16 C -0.0287(3) 0.18020(11) 0.6896(2) 0.0339(5) Uani 1 1 d . . . H16A H -0.0136 0.2229 0.7050 0.051 Uiso 1 1 calc R . . H16B H 0.0616 0.1595 0.7657 0.051 Uiso 1 1 calc R . . H16C H -0.1246 0.1684 0.6967 0.051 Uiso 1 1 calc R . . C17 C -0.0944(2) 0.08091(9) 0.4644(2) 0.0236(4) Uani 1 1 d . . . H17A H -0.1954 0.0727 0.4656 0.035 Uiso 1 1 calc R . . H17B H -0.0119 0.0573 0.5412 0.035 Uiso 1 1 calc R . . H17C H -0.1010 0.0707 0.3670 0.035 Uiso 1 1 calc R . . C18 C -0.2078(2) 0.20595(10) 0.3609(3) 0.0330(5) Uani 1 1 d . . . H18A H -0.2157 0.1976 0.2621 0.049 Uiso 1 1 calc R . . H18B H -0.1850 0.2479 0.3837 0.049 Uiso 1 1 calc R . . H18C H -0.3074 0.1960 0.3630 0.049 Uiso 1 1 calc R . . N1 N 0.47818(18) 0.09669(7) 0.48158(18) 0.0189(3) Uani 1 1 d . . . N2 N 0.37739(18) 0.14601(6) 0.47049(17) 0.0184(3) Uani 1 1 d . . . O1 O 0.51214(15) 0.01250(6) 0.34516(15) 0.0227(3) Uani 1 1 d . . . O2 O 0.47692(17) 0.11237(6) 0.23424(15) 0.0260(3) Uani 1 1 d . . . Si1 Si -0.04680(6) 0.16079(2) 0.50165(6) 0.02014(16) Uani 1 1 d . . . S1 S 0.43646(5) 0.069347(19) 0.31572(5) 0.01837(15) Uani 1 1 d . . . H1 H 0.472(3) 0.0699(12) 0.532(3) 0.038(7) Uiso 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 C11 0.0177(10) 0.0300(11) 0.0308(11) 0.0064(8) 0.0095(9) 0.0021(8) C1 0.0206(11) 0.0539(15) 0.0289(11) 0.0010(10) 0.0086(9) 0.0011(10) C2 0.0189(10) 0.0358(11) 0.0179(9) -0.0034(8) 0.0070(8) 0.0011(9) C3 0.0264(11) 0.0254(11) 0.0274(11) 0.0032(8) 0.0059(9) 0.0065(9) C4 0.0277(11) 0.0192(9) 0.0282(10) 0.0020(8) 0.0091(9) -0.0002(8) C5 0.0185(9) 0.0177(9) 0.0222(9) -0.0009(7) 0.0109(8) -0.0006(7) C6 0.0224(10) 0.0195(9) 0.0237(9) 0.0020(7) 0.0120(8) 0.0018(8) C7 0.0226(10) 0.0280(10) 0.0242(9) 0.0009(8) 0.0132(8) -0.0036(8) C8 0.0187(10) 0.0181(9) 0.0256(10) -0.0029(7) 0.0101(8) -0.0060(7) C9 0.0179(10) 0.0236(10) 0.0243(10) -0.0009(7) 0.0077(8) -0.0027(8) C10 0.0149(9) 0.0171(9) 0.0275(10) 0.0011(7) 0.0096(8) 0.0030(7) C12 0.0143(9) 0.0137(8) 0.0272(10) -0.0006(7) 0.0107(8) -0.0010(7) C13 0.0162(9) 0.0175(9) 0.0231(9) -0.0013(7) 0.0090(8) 0.0004(7) C14 0.0237(10) 0.0144(9) 0.0245(10) -0.0008(7) 0.0096(8) 0.0006(8) C15 0.0278(11) 0.0158(9) 0.0261(10) -0.0022(7) 0.0124(9) -0.0053(8) C16 0.0318(12) 0.0372(12) 0.0393(12) -0.0092(10) 0.0216(11) 0.0032(10) C17 0.0206(10) 0.0247(10) 0.0275(10) -0.0001(8) 0.0125(9) -0.0029(8) C18 0.0203(11) 0.0299(11) 0.0463(13) 0.0072(10) 0.0124(10) 0.0038(9) N1 0.0156(8) 0.0171(8) 0.0253(8) 0.0014(6) 0.0102(7) 0.0031(6) N2 0.0160(8) 0.0142(7) 0.0271(8) -0.0015(6) 0.0114(7) -0.0008(6) O1 0.0223(7) 0.0183(7) 0.0325(8) 0.0005(5) 0.0166(6) 0.0029(6) O2 0.0292(8) 0.0214(7) 0.0332(8) 0.0028(6) 0.0193(7) -0.0047(6) Si1 0.0161(3) 0.0191(3) 0.0263(3) -0.0012(2) 0.0104(2) 0.0026(2) S1 0.0178(3) 0.0155(3) 0.0254(3) 0.00061(17) 0.0128(2) -0.00002(17) _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 C11 C10 1.316(3) . ? C11 H11A 0.9500 . ? C11 H11B 0.9500 . ? C1 C2 1.507(3) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C2 C3 1.393(3) . ? C2 C7 1.392(3) . ? C3 C4 1.387(3) . ? C3 H3 0.9500 . ? C4 C5 1.388(3) . ? C4 H4 0.9500 . ? C5 C6 1.386(3) . ? C5 S1 1.7656(19) . ? C6 C7 1.388(3) . ? C6 H6 0.9500 . ? C7 H7 0.9500 . ? C8 N2 1.489(2) . ? C8 C15 1.535(3) . ? C8 C9 1.544(3) . ? C8 H8 1.0000 . ? C9 C10 1.517(3) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 C12 1.527(3) . ? C12 N2 1.495(2) . ? C12 C13 1.542(2) . ? C12 H12 1.0000 . ? C13 C14 1.542(3) . ? C13 Si1 1.8950(19) . ? C13 H13 1.0000 . ? C14 C15 1.536(3) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 Si1 1.870(2) . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C17 Si1 1.864(2) . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C18 Si1 1.864(2) . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? N1 N2 1.443(2) . ? N1 S1 1.6527(16) . ? N1 H1 0.81(3) . ? O1 S1 1.4407(14) . ? O2 S1 1.4294(13) . ? 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 C10 C11 H11A 120.0 . . ? C10 C11 H11B 120.0 . . ? H11A C11 H11B 120.0 . . ? C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? C3 C2 C7 118.14(18) . . ? C3 C2 C1 120.8(2) . . ? C7 C2 C1 121.1(2) . . ? C4 C3 C2 121.30(19) . . ? C4 C3 H3 119.3 . . ? C2 C3 H3 119.3 . . ? C3 C4 C5 119.11(19) . . ? C3 C4 H4 120.4 . . ? C5 C4 H4 120.4 . . ? C6 C5 C4 120.98(18) . . ? C6 C5 S1 120.11(15) . . ? C4 C5 S1 118.80(15) . . ? C5 C6 C7 118.84(18) . . ? C5 C6 H6 120.6 . . ? C7 C6 H6 120.6 . . ? C6 C7 C2 121.61(19) . . ? C6 C7 H7 119.2 . . ? C2 C7 H7 119.2 . . ? N2 C8 C15 106.29(15) . . ? N2 C8 C9 104.35(14) . . ? C15 C8 C9 112.29(15) . . ? N2 C8 H8 111.2 . . ? C15 C8 H8 111.2 . . ? C9 C8 H8 111.2 . . ? C10 C9 C8 103.40(15) . . ? C10 C9 H9A 111.1 . . ? C8 C9 H9A 111.1 . . ? C10 C9 H9B 111.1 . . ? C8 C9 H9B 111.1 . . ? H9A C9 H9B 109.0 . . ? C11 C10 C9 127.46(18) . . ? C11 C10 C12 125.73(18) . . ? C9 C10 C12 106.79(15) . . ? N2 C12 C10 103.85(14) . . ? N2 C12 C13 106.27(14) . . ? C10 C12 C13 112.40(14) . . ? N2 C12 H12 111.3 . . ? C10 C12 H12 111.3 . . ? C13 C12 H12 111.3 . . ? C14 C13 C12 108.97(15) . . ? C14 C13 Si1 114.35(12) . . ? C12 C13 Si1 116.15(12) . . ? C14 C13 H13 105.5 . . ? C12 C13 H13 105.5 . . ? Si1 C13 H13 105.5 . . ? C15 C14 C13 111.94(15) . . ? C15 C14 H14A 109.2 . . ? C13 C14 H14A 109.2 . . ? C15 C14 H14B 109.2 . . ? C13 C14 H14B 109.2 . . ? H14A C14 H14B 107.9 . . ? C8 C15 C14 111.31(15) . . ? C8 C15 H15A 109.4 . . ? C14 C15 H15A 109.4 . . ? C8 C15 H15B 109.4 . . ? C14 C15 H15B 109.4 . . ? H15A C15 H15B 108.0 . . ? Si1 C16 H16A 109.5 . . ? Si1 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? Si1 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? Si1 C17 H17A 109.5 . . ? Si1 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? Si1 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 . . ? N2 N1 S1 110.88(12) . . ? N2 N1 H1 113.3(18) . . ? S1 N1 H1 107.6(18) . . ? N1 N2 C8 110.11(14) . . ? N1 N2 C12 110.37(13) . . ? C8 N2 C12 101.98(13) . . ? C17 Si1 C18 109.66(10) . . ? C17 Si1 C16 109.71(10) . . ? C18 Si1 C16 108.41(11) . . ? C17 Si1 C13 109.41(9) . . ? C18 Si1 C13 106.76(9) . . ? C16 Si1 C13 112.81(9) . . ? O2 S1 O1 119.50(8) . . ? O2 S1 N1 108.36(9) . . ? O1 S1 N1 104.61(8) . . ? O2 S1 C5 107.64(9) . . ? O1 S1 C5 109.32(8) . . ? N1 S1 C5 106.74(8) . . ? _diffrn_measured_fraction_theta_max 0.974 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.974 _refine_diff_density_max 0.609 _refine_diff_density_min -0.603 _refine_diff_density_rms 0.068