# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_cambridge 0177 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Veejendra Yadav' _publ_contact_author_email vijendra@iitk.ac.in loop_ _publ_author_name V.Yadav B.Narhe data_bharat _database_code_depnum_ccdc_archive 'CCDC 859591' #TrackingRef '1a.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common azetidine _chemical_melting_point ? _chemical_formula_moiety 'C27 H33 N1 O2 S1 Si1' _chemical_formula_sum 'C27 H33 N1 O2 S1 Si1' _chemical_formula_weight 463.7 _chemical_absolute_configuration rmad 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 'C 1 2 1' _symmetry_space_group_name_HALL 'C 2y' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z' _cell_length_a 18.687(5) _cell_length_b 8.149(5) _cell_length_c 18.235(5) _cell_angle_alpha 90.000(5) _cell_angle_beta 115.580(5) _cell_angle_gamma 90.000(5) _cell_volume 2504.7(18) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min 2.2 _cell_measurement_theta_max 25.5 _exptl_crystal_description cuboid _exptl_crystal_colour ' colorless' _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 1.230 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 992 _exptl_absorpt_coefficient_mu 0.201 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_correction_T_min 0.9609 _exptl_absorpt_correction_T_max 0.9609 _exptl_absorpt_process_details '(North et al., 1968)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71069 _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-Omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 6730 _diffrn_reflns_av_R_equivalents 0.0432 _diffrn_reflns_av_sigmaI/netI 0.0747 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.19 _diffrn_reflns_theta_max 25.49 _reflns_number_total 4223 _reflns_number_gt 3702 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART 5.628 (Bruker, 2003)' _computing_cell_refinement 'SMART 5.628 (Bruker, 2003)' _computing_data_reduction 'SAINT+ 6.45 (Bruker, 2003)' _computing_structure_solution Sir92 _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'DIAMOND 3.1d' _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^)+(0.0536P)^2^+1.0760P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.07(11) _refine_ls_number_reflns 4223 _refine_ls_number_parameters 293 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0623 _refine_ls_R_factor_gt 0.0521 _refine_ls_wR_factor_ref 0.1231 _refine_ls_wR_factor_gt 0.1137 _refine_ls_goodness_of_fit_ref 1.043 _refine_ls_restrained_S_all 1.043 _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 C1 C 0.2805(2) 0.2430(4) 0.1562(2) 0.0229(8) Uani 1 1 d . . . H1 H 0.2564 0.3135 0.1829 0.027 Uiso 1 1 calc R . . C2 C 0.3562(2) 0.3232(5) 0.1586(2) 0.0279(8) Uani 1 1 d . . . H2A H 0.3819 0.3989 0.2034 0.033 Uiso 1 1 calc R . . H2B H 0.3940 0.2457 0.1549 0.033 Uiso 1 1 calc R . . C3 C 0.3032(2) 0.4067(5) 0.0776(2) 0.0277(9) Uani 1 1 d . . . H3A H 0.2856 0.5159 0.0834 0.033 Uiso 1 1 calc R . . H3B H 0.3248 0.4052 0.0378 0.033 Uiso 1 1 calc R . . C4 C 0.2833(2) 0.0656(4) 0.1837(2) 0.0237(8) Uani 1 1 d . . . H4A H 0.3128 0.0010 0.1613 0.028 Uiso 1 1 calc R . . H4B H 0.2297 0.0228 0.1616 0.028 Uiso 1 1 calc R . . C5 C 0.2639(2) 0.1391(5) 0.3384(2) 0.0272(9) Uani 1 1 d . . . C6 C 0.2865(2) 0.1601(5) 0.4218(2) 0.0338(10) Uani 1 1 d . . . H6 H 0.3377 0.1317 0.4588 0.041 Uiso 1 1 calc R . . C7 C 0.2342(3) 0.2221(6) 0.4503(3) 0.0403(11) Uani 1 1 d . . . H7 H 0.2504 0.2349 0.5059 0.048 Uiso 1 1 calc R . . C8 C 0.1577(2) 0.2652(6) 0.3961(3) 0.0415(11) Uani 1 1 d . . . H8 H 0.1225 0.3065 0.4152 0.050 Uiso 1 1 calc R . . C9 C 0.1344(2) 0.2468(5) 0.3145(2) 0.0373(10) Uani 1 1 d . . . H9 H 0.0833 0.2768 0.2779 0.045 Uiso 1 1 calc R . . C10 C 0.1867(2) 0.1834(5) 0.2861(2) 0.0286(9) Uani 1 1 d . . . H10 H 0.1695 0.1702 0.2304 0.034 Uiso 1 1 calc R . . C11 C 0.4297(2) 0.1462(5) 0.3385(2) 0.0285(9) Uani 1 1 d . . . C12 C 0.4897(2) 0.0918(5) 0.3173(2) 0.0340(10) Uani 1 1 d . . . H12 H 0.4822 -0.0048 0.2877 0.041 Uiso 1 1 calc R . . C13 C 0.5595(2) 0.1781(6) 0.3393(3) 0.0385(10) Uani 1 1 d . . . H13 H 0.5986 0.1379 0.3255 0.046 Uiso 1 1 calc R . . C14 C 0.5715(2) 0.3234(6) 0.3816(2) 0.0330(9) Uani 1 1 d . . . H14 H 0.6177 0.3836 0.3947 0.040 Uiso 1 1 calc R . . C15 C 0.5142(2) 0.3785(5) 0.4043(2) 0.0339(9) Uani 1 1 d . . . H15 H 0.5225 0.4748 0.4342 0.041 Uiso 1 1 calc R . . C16 C 0.4443(2) 0.2917(5) 0.3830(2) 0.0303(8) Uani 1 1 d . . . H16 H 0.4063 0.3312 0.3987 0.036 Uiso 1 1 calc R . . C17 C 0.3382(2) -0.1895(5) 0.3229(2) 0.0280(8) Uani 1 1 d . . . C18 C 0.3727(4) -0.2868(6) 0.2742(3) 0.0564(14) Uani 1 1 d . . . H18A H 0.4252 -0.2477 0.2868 0.085 Uiso 1 1 calc R . . H18B H 0.3396 -0.2730 0.2172 0.085 Uiso 1 1 calc R . . H18C H 0.3750 -0.4010 0.2880 0.085 Uiso 1 1 calc R . . C19 C 0.3905(2) -0.2138(6) 0.4135(2) 0.0422(10) Uani 1 1 d . . . H19A H 0.3936 -0.3285 0.4264 0.063 Uiso 1 1 calc R . . H19B H 0.3682 -0.1555 0.4444 0.063 Uiso 1 1 calc R . . H19C H 0.4428 -0.1725 0.4267 0.063 Uiso 1 1 calc R . . C20 C 0.2556(3) -0.2562(6) 0.3031(3) 0.0535(13) Uani 1 1 d . . . H20A H 0.2595 -0.3696 0.3188 0.080 Uiso 1 1 calc R . . H20B H 0.2228 -0.2466 0.2458 0.080 Uiso 1 1 calc R . . H20C H 0.2325 -0.1946 0.3324 0.080 Uiso 1 1 calc R . . C21 C 0.1185(2) 0.4695(5) 0.0523(2) 0.0237(8) Uani 1 1 d . . . C22 C 0.1347(2) 0.6275(5) 0.0352(2) 0.0252(8) Uani 1 1 d . . . H22 H 0.1623 0.6433 0.0037 0.030 Uiso 1 1 calc R . . C23 C 0.1101(2) 0.7603(5) 0.0647(2) 0.0261(8) Uani 1 1 d . . . H23 H 0.1216 0.8657 0.0534 0.031 Uiso 1 1 calc R . . C24 C 0.0681(2) 0.7398(5) 0.1111(2) 0.0257(8) Uani 1 1 d . . . C25 C 0.0521(2) 0.5810(5) 0.1275(2) 0.0269(9) Uani 1 1 d . . . H25 H 0.0237 0.5654 0.1581 0.032 Uiso 1 1 calc R . . C26 C 0.0773(2) 0.4461(5) 0.0996(2) 0.0276(9) Uani 1 1 d . . . H26 H 0.0670 0.3407 0.1121 0.033 Uiso 1 1 calc R . . C27 C 0.0384(2) 0.8886(5) 0.1391(2) 0.0313(9) Uani 1 1 d . . . H27A H -0.0176 0.9008 0.1063 0.047 Uiso 1 1 calc R . . H27B H 0.0655 0.9847 0.1338 0.047 Uiso 1 1 calc R . . H27C H 0.0484 0.8748 0.1950 0.047 Uiso 1 1 calc R . . N1 N 0.24331(16) 0.2744(4) 0.06563(16) 0.0243(7) Uani 1 1 d . . . O1 O 0.11035(15) 0.1575(3) 0.02516(15) 0.0287(6) Uani 1 1 d . . . O2 O 0.13720(15) 0.3420(3) -0.06804(14) 0.0313(6) Uani 1 1 d . . . Si1 Si 0.33017(6) 0.03943(13) 0.29708(6) 0.0241(2) Uani 1 1 d . . . S1 S 0.14822(5) 0.30063(11) 0.01215(5) 0.0244(2) 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 0.0255(18) 0.023(2) 0.0214(18) -0.0013(14) 0.0117(15) 0.0013(15) C2 0.0247(17) 0.030(2) 0.0293(19) -0.0005(17) 0.0116(15) -0.0006(17) C3 0.032(2) 0.022(2) 0.034(2) -0.0041(16) 0.0192(17) -0.0042(17) C4 0.0257(18) 0.024(2) 0.0225(18) -0.0006(15) 0.0114(15) 0.0011(16) C5 0.0242(18) 0.030(2) 0.028(2) -0.0009(17) 0.0118(16) -0.0027(17) C6 0.0260(19) 0.044(3) 0.029(2) -0.0068(18) 0.0102(17) -0.0006(19) C7 0.043(2) 0.054(3) 0.028(2) -0.0079(19) 0.019(2) -0.001(2) C8 0.039(2) 0.054(3) 0.041(2) -0.004(2) 0.0264(19) 0.007(2) C9 0.028(2) 0.049(3) 0.037(2) 0.006(2) 0.0155(18) 0.0099(19) C10 0.031(2) 0.029(2) 0.027(2) -0.0014(16) 0.0145(17) -0.0028(17) C11 0.029(2) 0.030(2) 0.028(2) 0.0080(16) 0.0136(17) 0.0056(17) C12 0.034(2) 0.033(2) 0.036(2) -0.0027(18) 0.0159(18) 0.0010(18) C13 0.026(2) 0.046(3) 0.043(3) 0.001(2) 0.0145(19) 0.002(2) C14 0.0247(18) 0.037(3) 0.033(2) 0.0057(19) 0.0084(16) -0.0043(19) C15 0.039(2) 0.032(2) 0.025(2) 0.0003(17) 0.0087(18) -0.0046(18) C16 0.0293(19) 0.031(2) 0.0310(19) 0.0007(19) 0.0137(16) 0.0043(19) C17 0.0298(18) 0.027(2) 0.0243(17) 0.0026(17) 0.0090(14) 0.0003(19) C18 0.102(4) 0.028(3) 0.052(3) 0.009(2) 0.046(3) 0.018(3) C19 0.051(2) 0.037(3) 0.034(2) 0.011(2) 0.0133(19) 0.007(2) C20 0.044(3) 0.036(3) 0.067(3) 0.018(2) 0.011(2) -0.002(2) C21 0.0231(18) 0.024(2) 0.023(2) -0.0025(15) 0.0092(16) -0.0013(16) C22 0.0248(19) 0.028(2) 0.0241(19) 0.0028(16) 0.0120(16) 0.0007(16) C23 0.0258(18) 0.023(2) 0.0267(19) -0.0007(15) 0.0091(16) -0.0017(16) C24 0.0225(18) 0.029(2) 0.0220(18) -0.0012(15) 0.0061(15) 0.0005(16) C25 0.0223(18) 0.030(2) 0.031(2) -0.0004(16) 0.0142(16) -0.0029(16) C26 0.0256(19) 0.031(2) 0.024(2) 0.0055(16) 0.0085(16) 0.0001(17) C27 0.031(2) 0.028(2) 0.039(2) -0.0019(18) 0.0185(18) -0.0006(17) N1 0.0274(15) 0.0248(19) 0.0237(15) -0.0009(13) 0.0139(12) -0.0004(14) O1 0.0304(14) 0.0212(14) 0.0332(15) -0.0014(11) 0.0125(12) -0.0037(11) O2 0.0415(14) 0.0292(16) 0.0223(12) 0.0002(11) 0.0128(11) 0.0049(12) Si1 0.0255(5) 0.0258(6) 0.0221(5) -0.0003(4) 0.0113(4) 0.0019(5) S1 0.0278(4) 0.0216(5) 0.0232(4) 0.0002(4) 0.0104(4) 0.0005(4) _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 N1 1.511(4) . ? C1 C4 1.524(5) . ? C1 C2 1.542(5) . ? C1 H1 0.9800 . ? C2 C3 1.537(5) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 N1 1.500(5) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 Si1 1.878(3) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 C10 1.391(5) . ? C5 C6 1.403(5) . ? C5 Si1 1.889(4) . ? C6 C7 1.386(5) . ? C6 H6 0.9300 . ? C7 C8 1.386(6) . ? C7 H7 0.9300 . ? C8 C9 1.366(6) . ? C8 H8 0.9300 . ? C9 C10 1.389(5) . ? C9 H9 0.9300 . ? C10 H10 0.9300 . ? C11 C16 1.395(6) . ? C11 C12 1.406(5) . ? C11 Si1 1.890(4) . ? C12 C13 1.379(6) . ? C12 H12 0.9300 . ? C13 C14 1.377(6) . ? C13 H13 0.9300 . ? C14 C15 1.380(5) . ? C14 H14 0.9300 . ? C15 C16 1.385(5) . ? C15 H15 0.9300 . ? C16 H16 0.9300 . ? C17 C20 1.525(5) . ? C17 C18 1.526(6) . ? C17 C19 1.526(5) . ? C17 Si1 1.914(5) . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? C20 H20A 0.9600 . ? C20 H20B 0.9600 . ? C20 H20C 0.9600 . ? C21 C22 1.389(5) . ? C21 C26 1.395(5) . ? C21 S1 1.757(4) . ? C22 C23 1.374(5) . ? C22 H22 0.9300 . ? C23 C24 1.389(5) . ? C23 H23 0.9300 . ? C24 C25 1.390(5) . ? C24 C27 1.512(5) . ? C25 C26 1.378(5) . ? C25 H25 0.9300 . ? C26 H26 0.9300 . ? C27 H27A 0.9600 . ? C27 H27B 0.9600 . ? C27 H27C 0.9600 . ? N1 S1 1.630(3) . ? O1 S1 1.436(3) . ? O2 S1 1.426(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 N1 C1 C4 117.0(3) . . ? N1 C1 C2 86.7(2) . . ? C4 C1 C2 119.4(3) . . ? N1 C1 H1 110.5 . . ? C4 C1 H1 110.5 . . ? C2 C1 H1 110.5 . . ? C3 C2 C1 87.5(3) . . ? C3 C2 H2A 114.1 . . ? C1 C2 H2A 114.1 . . ? C3 C2 H2B 114.1 . . ? C1 C2 H2B 114.1 . . ? H2A C2 H2B 111.2 . . ? N1 C3 C2 87.3(3) . . ? N1 C3 H3A 114.1 . . ? C2 C3 H3A 114.1 . . ? N1 C3 H3B 114.1 . . ? C2 C3 H3B 114.1 . . ? H3A C3 H3B 111.3 . . ? C1 C4 Si1 113.8(2) . . ? C1 C4 H4A 108.8 . . ? Si1 C4 H4A 108.8 . . ? C1 C4 H4B 108.8 . . ? Si1 C4 H4B 108.8 . . ? H4A C4 H4B 107.7 . . ? C10 C5 C6 116.7(3) . . ? C10 C5 Si1 120.2(3) . . ? C6 C5 Si1 122.9(3) . . ? C7 C6 C5 121.3(4) . . ? C7 C6 H6 119.3 . . ? C5 C6 H6 119.3 . . ? C8 C7 C6 120.1(4) . . ? C8 C7 H7 119.9 . . ? C6 C7 H7 119.9 . . ? C9 C8 C7 119.7(4) . . ? C9 C8 H8 120.1 . . ? C7 C8 H8 120.1 . . ? C8 C9 C10 120.1(4) . . ? C8 C9 H9 119.9 . . ? C10 C9 H9 119.9 . . ? C5 C10 C9 122.0(4) . . ? C5 C10 H10 119.0 . . ? C9 C10 H10 119.0 . . ? C16 C11 C12 116.6(4) . . ? C16 C11 Si1 122.4(3) . . ? C12 C11 Si1 120.6(3) . . ? C13 C12 C11 121.7(4) . . ? C13 C12 H12 119.2 . . ? C11 C12 H12 119.2 . . ? C14 C13 C12 120.4(4) . . ? C14 C13 H13 119.8 . . ? C12 C13 H13 119.8 . . ? C13 C14 C15 119.1(4) . . ? C13 C14 H14 120.4 . . ? C15 C14 H14 120.4 . . ? C14 C15 C16 120.7(4) . . ? C14 C15 H15 119.7 . . ? C16 C15 H15 119.7 . . ? C15 C16 C11 121.4(3) . . ? C15 C16 H16 119.3 . . ? C11 C16 H16 119.3 . . ? C20 C17 C18 108.4(4) . . ? C20 C17 C19 108.7(3) . . ? C18 C17 C19 109.2(3) . . ? C20 C17 Si1 109.0(3) . . ? C18 C17 Si1 111.8(3) . . ? C19 C17 Si1 109.8(3) . . ? C17 C18 H18A 109.5 . . ? C17 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C17 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C17 C19 H19A 109.5 . . ? C17 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C17 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C17 C20 H20A 109.5 . . ? C17 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C17 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C22 C21 C26 119.9(3) . . ? C22 C21 S1 119.6(3) . . ? C26 C21 S1 120.6(3) . . ? C23 C22 C21 120.0(3) . . ? C23 C22 H22 120.0 . . ? C21 C22 H22 120.0 . . ? C22 C23 C24 121.1(4) . . ? C22 C23 H23 119.5 . . ? C24 C23 H23 119.5 . . ? C23 C24 C25 118.3(3) . . ? C23 C24 C27 119.7(3) . . ? C25 C24 C27 121.9(3) . . ? C26 C25 C24 121.5(3) . . ? C26 C25 H25 119.2 . . ? C24 C25 H25 119.2 . . ? C25 C26 C21 119.2(4) . . ? C25 C26 H26 120.4 . . ? C21 C26 H26 120.4 . . ? C24 C27 H27A 109.5 . . ? C24 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? C24 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? C3 N1 C1 90.1(2) . . ? C3 N1 S1 123.0(2) . . ? C1 N1 S1 123.0(2) . . ? C4 Si1 C11 107.33(16) . . ? C4 Si1 C5 108.45(16) . . ? C11 Si1 C5 110.13(17) . . ? C4 Si1 C17 109.37(16) . . ? C11 Si1 C17 113.05(16) . . ? C5 Si1 C17 108.42(17) . . ? O2 S1 O1 119.88(16) . . ? O2 S1 N1 106.37(15) . . ? O1 S1 N1 106.41(16) . . ? O2 S1 C21 108.04(17) . . ? O1 S1 C21 107.47(16) . . ? N1 S1 C21 108.21(15) . . ? 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 N1 C1 C2 C3 21.4(3) . . . . ? C4 C1 C2 C3 140.7(3) . . . . ? C1 C2 C3 N1 -21.5(3) . . . . ? N1 C1 C4 Si1 -179.8(2) . . . . ? C2 C1 C4 Si1 77.9(3) . . . . ? C10 C5 C6 C7 -0.1(6) . . . . ? Si1 C5 C6 C7 -175.0(3) . . . . ? C5 C6 C7 C8 -0.1(7) . . . . ? C6 C7 C8 C9 -0.3(7) . . . . ? C7 C8 C9 C10 0.7(7) . . . . ? C6 C5 C10 C9 0.6(6) . . . . ? Si1 C5 C10 C9 175.6(3) . . . . ? C8 C9 C10 C5 -0.9(6) . . . . ? C16 C11 C12 C13 -0.1(6) . . . . ? Si1 C11 C12 C13 172.8(3) . . . . ? C11 C12 C13 C14 -1.4(6) . . . . ? C12 C13 C14 C15 2.3(6) . . . . ? C13 C14 C15 C16 -1.8(6) . . . . ? C14 C15 C16 C11 0.3(6) . . . . ? C12 C11 C16 C15 0.7(5) . . . . ? Si1 C11 C16 C15 -172.1(3) . . . . ? C26 C21 C22 C23 -0.2(5) . . . . ? S1 C21 C22 C23 178.5(3) . . . . ? C21 C22 C23 C24 -0.6(5) . . . . ? C22 C23 C24 C25 0.4(5) . . . . ? C22 C23 C24 C27 -177.0(3) . . . . ? C23 C24 C25 C26 0.5(5) . . . . ? C27 C24 C25 C26 177.9(4) . . . . ? C24 C25 C26 C21 -1.3(5) . . . . ? C22 C21 C26 C25 1.1(5) . . . . ? S1 C21 C26 C25 -177.5(3) . . . . ? C2 C3 N1 C1 22.0(3) . . . . ? C2 C3 N1 S1 152.4(2) . . . . ? C4 C1 N1 C3 -143.5(3) . . . . ? C2 C1 N1 C3 -21.9(3) . . . . ? C4 C1 N1 S1 86.0(3) . . . . ? C2 C1 N1 S1 -152.4(3) . . . . ? C1 C4 Si1 C11 -52.0(3) . . . . ? C1 C4 Si1 C5 66.9(3) . . . . ? C1 C4 Si1 C17 -175.0(2) . . . . ? C16 C11 Si1 C4 109.3(3) . . . . ? C12 C11 Si1 C4 -63.2(3) . . . . ? C16 C11 Si1 C5 -8.6(4) . . . . ? C12 C11 Si1 C5 178.9(3) . . . . ? C16 C11 Si1 C17 -130.1(3) . . . . ? C12 C11 Si1 C17 57.5(4) . . . . ? C10 C5 Si1 C4 13.8(4) . . . . ? C6 C5 Si1 C4 -171.5(3) . . . . ? C10 C5 Si1 C11 130.9(3) . . . . ? C6 C5 Si1 C11 -54.3(4) . . . . ? C10 C5 Si1 C17 -104.9(3) . . . . ? C6 C5 Si1 C17 69.8(4) . . . . ? C20 C17 Si1 C4 -72.3(3) . . . . ? C18 C17 Si1 C4 47.5(3) . . . . ? C19 C17 Si1 C4 168.8(2) . . . . ? C20 C17 Si1 C11 168.2(3) . . . . ? C18 C17 Si1 C11 -72.0(3) . . . . ? C19 C17 Si1 C11 49.2(3) . . . . ? C20 C17 Si1 C5 45.8(3) . . . . ? C18 C17 Si1 C5 165.6(3) . . . . ? C19 C17 Si1 C5 -73.2(3) . . . . ? C3 N1 S1 O2 59.7(3) . . . . ? C1 N1 S1 O2 174.6(3) . . . . ? C3 N1 S1 O1 -171.5(3) . . . . ? C1 N1 S1 O1 -56.5(3) . . . . ? C3 N1 S1 C21 -56.2(3) . . . . ? C1 N1 S1 C21 58.8(3) . . . . ? C22 C21 S1 O2 -37.8(3) . . . . ? C26 C21 S1 O2 140.9(3) . . . . ? C22 C21 S1 O1 -168.5(3) . . . . ? C26 C21 S1 O1 10.2(3) . . . . ? C22 C21 S1 N1 77.0(3) . . . . ? C26 C21 S1 N1 -104.4(3) . . . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 25.49 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.372 _refine_diff_density_min -0.249 _refine_diff_density_rms 0.059 # Attachment '1f2.cif' data_shelxl _database_code_depnum_ccdc_archive 'CCDC 859592' #TrackingRef '1f2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 'trans allyl azetidine' _chemical_melting_point ? _chemical_formula_moiety 'C30 H37 N O2 S Si' _chemical_formula_sum 'C30 H37 N O2 S Si' _chemical_formula_weight 503.76 _chemical_absolute_configuration rmad 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 orthorhombic _symmetry_space_group_name_H-M P_21_21_21 _symmetry_space_group_name_HALL 'P 2ac 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 11.241(5) _cell_length_b 13.090(5) _cell_length_c 19.226(5) _cell_angle_alpha 90.000(5) _cell_angle_beta 90.000(5) _cell_angle_gamma 90.000(5) _cell_volume 2829.0(18) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description cuboid _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 1.183 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1080 _exptl_absorpt_coefficient_mu 0.183 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_correction_T_min 0.9643 _exptl_absorpt_correction_T_max 0.9643 _exptl_absorpt_process_details '(North et al., 1968)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71069 _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-Omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14880 _diffrn_reflns_av_R_equivalents 0.0419 _diffrn_reflns_av_sigmaI/netI 0.0440 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.10 _diffrn_reflns_theta_max 25.50 _reflns_number_total 5242 _reflns_number_gt 4937 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART 5.628 (Bruker, 2003)' _computing_cell_refinement 'SMART 5.628 (Bruker, 2003)' _computing_data_reduction 'SAINT+ 6.45 (Bruker, 2003)' _computing_structure_solution Sir92 _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'diamond 3.1d' _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^)+(0.0645P)^2^+0.5594P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.03(7) _refine_ls_number_reflns 5242 _refine_ls_number_parameters 320 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0408 _refine_ls_R_factor_gt 0.0381 _refine_ls_wR_factor_ref 0.0967 _refine_ls_wR_factor_gt 0.0941 _refine_ls_goodness_of_fit_ref 0.935 _refine_ls_restrained_S_all 0.935 _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 S1 S 0.00732(4) -0.35723(3) 0.50091(2) 0.02343(12) Uani 1 1 d . . . Si1 Si 0.01148(5) 0.03002(4) 0.58186(3) 0.02185(13) Uani 1 1 d . . . O1 O -0.05896(13) -0.44788(11) 0.48459(8) 0.0322(4) Uani 1 1 d . . . O2 O 0.06246(13) -0.29915(12) 0.44641(7) 0.0310(3) Uani 1 1 d . . . N1 N -0.08469(15) -0.28017(13) 0.53922(8) 0.0231(4) Uani 1 1 d . . . C19 C -0.16872(18) -0.19777(16) 0.61844(10) 0.0246(4) Uani 1 1 d . . . H19 H -0.2321 -0.1611 0.5939 0.030 Uiso 1 1 calc R . . C27 C 0.30665(19) -0.44910(17) 0.64741(11) 0.0286(5) Uani 1 1 d . . . C26 C 0.30471(19) -0.35250(17) 0.61770(10) 0.0272(5) Uani 1 1 d . . . H26 H 0.3660 -0.3069 0.6273 0.033 Uiso 1 1 calc R . . C24 C 0.12031(18) -0.39148(15) 0.56049(10) 0.0225(4) Uani 1 1 d . . . C2 C 0.2409(2) -0.02382(17) 0.63500(11) 0.0286(5) Uani 1 1 d . . . H2 H 0.2643 -0.0211 0.5886 0.034 Uiso 1 1 calc R . . C4 C 0.2909(2) -0.05533(16) 0.75436(12) 0.0325(5) Uani 1 1 d . . . H4 H 0.3468 -0.0720 0.7882 0.039 Uiso 1 1 calc R . . C25 C 0.21276(18) -0.32281(16) 0.57385(10) 0.0239(4) Uani 1 1 d . . . H25 H 0.2127 -0.2582 0.5537 0.029 Uiso 1 1 calc R . . C17 C -0.02393(19) -0.09203(14) 0.53412(10) 0.0243(4) Uani 1 1 d . . . H17A H -0.0922 -0.0796 0.5044 0.029 Uiso 1 1 calc R . . H17B H 0.0428 -0.1082 0.5041 0.029 Uiso 1 1 calc R . . C29 C 0.11924(19) -0.48718(16) 0.59110(10) 0.0265(4) Uani 1 1 d . . . H29 H 0.0564 -0.5318 0.5830 0.032 Uiso 1 1 calc R . . C21 C -0.17753(19) -0.17610(17) 0.69571(10) 0.0281(5) Uani 1 1 d . . . H21A H -0.1134 -0.2105 0.7200 0.034 Uiso 1 1 calc R . . H21B H -0.1696 -0.1033 0.7038 0.034 Uiso 1 1 calc R . . C18 C -0.05030(17) -0.18507(15) 0.57840(10) 0.0226(4) Uani 1 1 d . . . H18 H 0.0171 -0.1994 0.6093 0.027 Uiso 1 1 calc R . . C3 C 0.3242(2) -0.04987(17) 0.68535(12) 0.0328(5) Uani 1 1 d . . . H3 H 0.4024 -0.0636 0.6726 0.039 Uiso 1 1 calc R . . C1 C 0.12263(19) -0.00153(15) 0.65214(10) 0.0236(4) Uani 1 1 d . . . C28 C 0.2122(2) -0.51593(17) 0.63377(11) 0.0297(5) Uani 1 1 d . . . H28 H 0.2121 -0.5806 0.6537 0.036 Uiso 1 1 calc R . . C7 C -0.1270(2) 0.08420(16) 0.62190(11) 0.0261(4) Uani 1 1 d . . . C9 C -0.2231(2) 0.19953(18) 0.70409(13) 0.0381(6) Uani 1 1 d . . . H9 H -0.2176 0.2444 0.7415 0.046 Uiso 1 1 calc R . . C8 C -0.1213(2) 0.15359(16) 0.67721(11) 0.0308(5) Uani 1 1 d . . . H8 H -0.0476 0.1694 0.6965 0.037 Uiso 1 1 calc R . . C20 C -0.16845(18) -0.31096(16) 0.59550(11) 0.0252(4) Uani 1 1 d . . . H20A H -0.1344 -0.3574 0.6294 0.030 Uiso 1 1 calc R . . H20B H -0.2448 -0.3354 0.5789 0.030 Uiso 1 1 calc R . . C6 C 0.09122(19) -0.00961(15) 0.72286(10) 0.0257(4) Uani 1 1 d . . . H6 H 0.0130 0.0030 0.7361 0.031 Uiso 1 1 calc R . . C5 C 0.1741(2) -0.03598(16) 0.77321(11) 0.0300(5) Uani 1 1 d . . . H5 H 0.1513 -0.0407 0.8196 0.036 Uiso 1 1 calc R . . C22 C -0.2957(2) -0.21277(17) 0.72354(11) 0.0302(5) Uani 1 1 d . . . H22 H -0.3641 -0.1818 0.7064 0.036 Uiso 1 1 calc R . . C10 C -0.3330(2) 0.17785(19) 0.67462(14) 0.0431(6) Uani 1 1 d . . . H10 H -0.4010 0.2096 0.6917 0.052 Uiso 1 1 calc R . . C23 C -0.3090(2) -0.28453(18) 0.76977(12) 0.0367(5) Uani 1 1 d . . . H23A H -0.2426 -0.3173 0.7881 0.044 Uiso 1 1 calc R . . H23B H -0.3848 -0.3030 0.7844 0.044 Uiso 1 1 calc R . . C11 C -0.3418(2) 0.10951(19) 0.62018(14) 0.0390(6) Uani 1 1 d . . . H11 H -0.4158 0.0943 0.6011 0.047 Uiso 1 1 calc R . . C30 C 0.4109(2) -0.48393(19) 0.69117(12) 0.0389(6) Uani 1 1 d . . . H30A H 0.4757 -0.4367 0.6858 0.058 Uiso 1 1 calc R . . H30B H 0.4357 -0.5506 0.6763 0.058 Uiso 1 1 calc R . . H30C H 0.3876 -0.4865 0.7392 0.058 Uiso 1 1 calc R . . C12 C -0.2402(2) 0.06360(17) 0.59403(12) 0.0302(5) Uani 1 1 d . . . H12 H -0.2469 0.0180 0.5571 0.036 Uiso 1 1 calc R . . C16 C 0.1279(2) 0.21808(18) 0.55508(12) 0.0383(6) Uani 1 1 d . . . H16A H 0.1517 0.2693 0.5221 0.057 Uiso 1 1 calc R . . H16B H 0.1965 0.1940 0.5799 0.057 Uiso 1 1 calc R . . H16C H 0.0720 0.2469 0.5873 0.057 Uiso 1 1 calc R . . C13 C 0.06968(19) 0.12872(16) 0.51656(10) 0.0264(5) Uani 1 1 d . . . C14 C 0.1596(2) 0.08372(19) 0.46467(12) 0.0375(6) Uani 1 1 d . . . H14A H 0.1822 0.1353 0.4317 0.056 Uiso 1 1 calc R . . H14B H 0.1239 0.0272 0.4406 0.056 Uiso 1 1 calc R . . H14C H 0.2288 0.0606 0.4893 0.056 Uiso 1 1 calc R . . C15 C -0.0377(2) 0.16942(18) 0.47495(12) 0.0360(5) Uani 1 1 d . . . H15A H -0.0924 0.2024 0.5060 0.054 Uiso 1 1 calc R . . H15B H -0.0770 0.1136 0.4521 0.054 Uiso 1 1 calc R . . H15C H -0.0106 0.2176 0.4408 0.054 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 0.0207(2) 0.0249(2) 0.0246(2) -0.00236(18) -0.0024(2) 0.0023(2) Si1 0.0213(3) 0.0217(3) 0.0226(2) -0.0003(2) -0.0005(2) -0.0009(2) O1 0.0275(8) 0.0283(8) 0.0406(9) -0.0088(7) -0.0073(7) 0.0010(6) O2 0.0277(8) 0.0410(8) 0.0242(7) 0.0028(7) 0.0036(6) 0.0057(7) N1 0.0198(9) 0.0235(9) 0.0260(9) -0.0006(7) 0.0011(7) 0.0004(7) C19 0.0218(10) 0.0252(11) 0.0269(10) 0.0018(8) -0.0006(8) 0.0007(8) C27 0.0255(11) 0.0357(12) 0.0246(10) -0.0053(9) -0.0010(9) 0.0079(9) C26 0.0221(10) 0.0333(12) 0.0263(10) -0.0052(9) 0.0007(8) -0.0018(9) C24 0.0190(10) 0.0247(10) 0.0239(10) -0.0026(8) 0.0004(8) 0.0054(8) C2 0.0263(11) 0.0296(11) 0.0300(10) -0.0013(9) 0.0002(9) 0.0016(9) C4 0.0314(12) 0.0260(11) 0.0399(12) 0.0030(9) -0.0124(10) -0.0052(9) C25 0.0236(10) 0.0220(10) 0.0260(10) 0.0006(8) 0.0013(8) 0.0005(8) C17 0.0258(11) 0.0249(10) 0.0223(9) -0.0012(8) -0.0004(8) -0.0011(8) C29 0.0237(11) 0.0246(10) 0.0312(11) -0.0011(8) 0.0001(9) -0.0014(8) C21 0.0282(12) 0.0304(11) 0.0258(10) -0.0018(9) -0.0005(9) -0.0043(9) C18 0.0213(10) 0.0227(10) 0.0237(9) -0.0011(8) -0.0013(8) 0.0006(8) C3 0.0234(11) 0.0301(11) 0.0448(13) 0.0028(10) -0.0033(10) -0.0008(9) C1 0.0231(10) 0.0201(10) 0.0276(10) -0.0020(8) -0.0023(8) -0.0040(8) C28 0.0322(12) 0.0244(10) 0.0323(11) 0.0016(9) 0.0010(9) 0.0044(9) C7 0.0282(11) 0.0225(10) 0.0276(10) 0.0057(8) 0.0024(9) 0.0009(9) C9 0.0495(16) 0.0237(12) 0.0410(13) 0.0040(10) 0.0146(12) 0.0065(11) C8 0.0339(12) 0.0247(11) 0.0339(11) 0.0043(9) 0.0061(10) 0.0008(9) C20 0.0194(10) 0.0270(11) 0.0294(10) 0.0007(9) 0.0033(8) -0.0018(8) C6 0.0263(11) 0.0217(10) 0.0291(10) -0.0011(8) 0.0006(9) -0.0020(8) C5 0.0374(12) 0.0258(11) 0.0268(10) 0.0002(9) -0.0058(9) -0.0045(10) C22 0.0267(11) 0.0347(12) 0.0292(11) -0.0029(9) 0.0035(9) 0.0032(9) C10 0.0349(14) 0.0327(13) 0.0617(16) 0.0128(12) 0.0206(13) 0.0111(11) C23 0.0327(13) 0.0385(13) 0.0390(12) -0.0017(11) 0.0080(11) 0.0004(10) C11 0.0272(12) 0.0346(13) 0.0551(15) 0.0165(11) 0.0036(11) 0.0046(10) C30 0.0415(14) 0.0383(13) 0.0370(12) -0.0028(10) -0.0120(11) 0.0107(11) C12 0.0272(11) 0.0275(11) 0.0359(12) 0.0091(9) -0.0003(9) 0.0010(9) C16 0.0444(14) 0.0328(13) 0.0377(12) 0.0051(10) -0.0017(11) -0.0126(11) C13 0.0249(11) 0.0267(11) 0.0275(11) 0.0023(8) 0.0003(8) -0.0025(9) C14 0.0400(14) 0.0380(13) 0.0345(12) 0.0105(10) 0.0096(11) 0.0018(11) C15 0.0365(13) 0.0354(12) 0.0359(11) 0.0124(10) -0.0030(10) -0.0008(10) _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 1.4358(16) . ? S1 O2 1.4354(15) . ? S1 N1 1.6216(17) . ? S1 C24 1.768(2) . ? Si1 C7 1.876(2) . ? Si1 C1 1.886(2) . ? Si1 C17 1.885(2) . ? Si1 C13 1.917(2) . ? N1 C20 1.490(2) . ? N1 C18 1.506(3) . ? C19 C21 1.516(3) . ? C19 C20 1.546(3) . ? C19 C18 1.547(3) . ? C19 H19 0.9800 . ? C27 C26 1.388(3) . ? C27 C28 1.400(3) . ? C27 C30 1.513(3) . ? C26 C25 1.389(3) . ? C26 H26 0.9300 . ? C24 C29 1.384(3) . ? C24 C25 1.398(3) . ? C2 C3 1.390(3) . ? C2 C1 1.400(3) . ? C2 H2 0.9300 . ? C4 C3 1.380(3) . ? C4 C5 1.386(3) . ? C4 H4 0.9300 . ? C25 H25 0.9300 . ? C17 C18 1.515(3) . ? C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? C29 C28 1.381(3) . ? C29 H29 0.9300 . ? C21 C22 1.510(3) . ? C21 H21A 0.9700 . ? C21 H21B 0.9700 . ? C18 H18 0.9800 . ? C3 H3 0.9300 . ? C1 C6 1.409(3) . ? C28 H28 0.9300 . ? C7 C8 1.400(3) . ? C7 C12 1.406(3) . ? C9 C10 1.388(4) . ? C9 C8 1.393(3) . ? C9 H9 0.9300 . ? C8 H8 0.9300 . ? C20 H20A 0.9700 . ? C20 H20B 0.9700 . ? C6 C5 1.387(3) . ? C6 H6 0.9300 . ? C5 H5 0.9300 . ? C22 C23 1.302(3) . ? C22 H22 0.9300 . ? C10 C11 1.380(4) . ? C10 H10 0.9300 . ? C23 H23A 0.9300 . ? C23 H23B 0.9300 . ? C11 C12 1.386(3) . ? C11 H11 0.9300 . ? C30 H30A 0.9600 . ? C30 H30B 0.9600 . ? C30 H30C 0.9600 . ? C12 H12 0.9300 . ? C16 C13 1.531(3) . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 0.9600 . ? C13 C14 1.538(3) . ? C13 C15 1.543(3) . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 0.9600 . ? 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 120.14(9) . . ? O1 S1 N1 106.40(9) . . ? O2 S1 N1 106.11(9) . . ? O1 S1 C24 107.75(10) . . ? O2 S1 C24 107.28(9) . . ? N1 S1 C24 108.77(9) . . ? C7 Si1 C1 109.79(9) . . ? C7 Si1 C17 110.18(10) . . ? C1 Si1 C17 107.65(9) . . ? C7 Si1 C13 107.29(9) . . ? C1 Si1 C13 113.00(9) . . ? C17 Si1 C13 108.94(9) . . ? C20 N1 C18 91.29(14) . . ? C20 N1 S1 124.38(14) . . ? C18 N1 S1 125.29(13) . . ? C21 C19 C20 117.33(18) . . ? C21 C19 C18 121.60(18) . . ? C20 C19 C18 87.68(15) . . ? C21 C19 H19 109.5 . . ? C20 C19 H19 109.5 . . ? C18 C19 H19 109.5 . . ? C26 C27 C28 118.7(2) . . ? C26 C27 C30 121.0(2) . . ? C28 C27 C30 120.2(2) . . ? C25 C26 C27 121.1(2) . . ? C25 C26 H26 119.5 . . ? C27 C26 H26 119.5 . . ? C29 C24 C25 120.69(19) . . ? C29 C24 S1 119.91(16) . . ? C25 C24 S1 119.34(16) . . ? C3 C2 C1 121.8(2) . . ? C3 C2 H2 119.1 . . ? C1 C2 H2 119.1 . . ? C3 C4 C5 119.9(2) . . ? C3 C4 H4 120.0 . . ? C5 C4 H4 120.0 . . ? C26 C25 C24 118.99(19) . . ? C26 C25 H25 120.5 . . ? C24 C25 H25 120.5 . . ? C18 C17 Si1 116.67(13) . . ? C18 C17 H17A 108.1 . . ? Si1 C17 H17A 108.1 . . ? C18 C17 H17B 108.1 . . ? Si1 C17 H17B 108.1 . . ? H17A C17 H17B 107.3 . . ? C28 C29 C24 119.5(2) . . ? C28 C29 H29 120.2 . . ? C24 C29 H29 120.2 . . ? C22 C21 C19 110.20(18) . . ? C22 C21 H21A 109.6 . . ? C19 C21 H21A 109.6 . . ? C22 C21 H21B 109.6 . . ? C19 C21 H21B 109.6 . . ? H21A C21 H21B 108.1 . . ? N1 C18 C17 115.70(15) . . ? N1 C18 C19 86.51(14) . . ? C17 C18 C19 122.31(17) . . ? N1 C18 H18 110.1 . . ? C17 C18 H18 110.1 . . ? C19 C18 H18 110.1 . . ? C4 C3 C2 120.0(2) . . ? C4 C3 H3 120.0 . . ? C2 C3 H3 120.0 . . ? C2 C1 C6 116.72(19) . . ? C2 C1 Si1 120.38(16) . . ? C6 C1 Si1 122.81(16) . . ? C29 C28 C27 121.0(2) . . ? C29 C28 H28 119.5 . . ? C27 C28 H28 119.5 . . ? C8 C7 C12 117.1(2) . . ? C8 C7 Si1 121.23(17) . . ? C12 C7 Si1 121.45(16) . . ? C10 C9 C8 119.4(2) . . ? C10 C9 H9 120.3 . . ? C8 C9 H9 120.3 . . ? C9 C8 C7 121.6(2) . . ? C9 C8 H8 119.2 . . ? C7 C8 H8 119.2 . . ? N1 C20 C19 87.08(15) . . ? N1 C20 H20A 114.1 . . ? C19 C20 H20A 114.1 . . ? N1 C20 H20B 114.1 . . ? C19 C20 H20B 114.1 . . ? H20A C20 H20B 111.3 . . ? C5 C6 C1 121.6(2) . . ? C5 C6 H6 119.2 . . ? C1 C6 H6 119.2 . . ? C4 C5 C6 120.0(2) . . ? C4 C5 H5 120.0 . . ? C6 C5 H5 120.0 . . ? C23 C22 C21 124.9(2) . . ? C23 C22 H22 117.5 . . ? C21 C22 H22 117.5 . . ? C11 C10 C9 120.4(2) . . ? C11 C10 H10 119.8 . . ? C9 C10 H10 119.8 . . ? C22 C23 H23A 120.0 . . ? C22 C23 H23B 120.0 . . ? H23A C23 H23B 120.0 . . ? C10 C11 C12 119.8(2) . . ? C10 C11 H11 120.1 . . ? C12 C11 H11 120.1 . . ? C27 C30 H30A 109.5 . . ? C27 C30 H30B 109.5 . . ? H30A C30 H30B 109.5 . . ? C27 C30 H30C 109.5 . . ? H30A C30 H30C 109.5 . . ? H30B C30 H30C 109.5 . . ? C11 C12 C7 121.6(2) . . ? C11 C12 H12 119.2 . . ? C7 C12 H12 119.2 . . ? C13 C16 H16A 109.5 . . ? C13 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C13 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C16 C13 C14 108.99(19) . . ? C16 C13 C15 108.75(19) . . ? C14 C13 C15 108.07(17) . . ? C16 C13 Si1 110.13(14) . . ? C14 C13 Si1 113.02(15) . . ? C15 C13 Si1 107.77(14) . . ? C13 C14 H14A 109.5 . . ? C13 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C13 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C13 C15 H15A 109.5 . . ? C13 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C13 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 S1 N1 C20 45.79(17) . . . . ? O2 S1 N1 C20 174.83(15) . . . . ? C24 S1 N1 C20 -70.04(18) . . . . ? O1 S1 N1 C18 166.97(15) . . . . ? O2 S1 N1 C18 -63.99(17) . . . . ? C24 S1 N1 C18 51.14(18) . . . . ? C28 C27 C26 C25 -1.6(3) . . . . ? C30 C27 C26 C25 175.77(19) . . . . ? O1 S1 C24 C29 -10.57(19) . . . . ? O2 S1 C24 C29 -141.24(16) . . . . ? N1 S1 C24 C29 104.38(17) . . . . ? O1 S1 C24 C25 166.71(15) . . . . ? O2 S1 C24 C25 36.04(18) . . . . ? N1 S1 C24 C25 -78.33(18) . . . . ? C27 C26 C25 C24 0.8(3) . . . . ? C29 C24 C25 C26 0.8(3) . . . . ? S1 C24 C25 C26 -176.42(15) . . . . ? C7 Si1 C17 C18 -73.09(17) . . . . ? C1 Si1 C17 C18 46.60(18) . . . . ? C13 Si1 C17 C18 169.47(15) . . . . ? C25 C24 C29 C28 -1.8(3) . . . . ? S1 C24 C29 C28 175.48(16) . . . . ? C20 C19 C21 C22 -64.4(2) . . . . ? C18 C19 C21 C22 -169.71(18) . . . . ? C20 N1 C18 C17 -145.16(18) . . . . ? S1 N1 C18 C17 79.8(2) . . . . ? C20 N1 C18 C19 -20.77(15) . . . . ? S1 N1 C18 C19 -155.84(14) . . . . ? Si1 C17 C18 N1 176.87(13) . . . . ? Si1 C17 C18 C19 73.9(2) . . . . ? C21 C19 C18 N1 141.0(2) . . . . ? C20 C19 C18 N1 19.99(14) . . . . ? C21 C19 C18 C17 -100.7(2) . . . . ? C20 C19 C18 C17 138.38(18) . . . . ? C5 C4 C3 C2 0.7(3) . . . . ? C1 C2 C3 C4 0.7(3) . . . . ? C3 C2 C1 C6 -1.7(3) . . . . ? C3 C2 C1 Si1 -178.35(16) . . . . ? C7 Si1 C1 C2 -167.33(16) . . . . ? C17 Si1 C1 C2 72.73(18) . . . . ? C13 Si1 C1 C2 -47.60(19) . . . . ? C7 Si1 C1 C6 16.28(19) . . . . ? C17 Si1 C1 C6 -103.66(17) . . . . ? C13 Si1 C1 C6 136.01(16) . . . . ? C24 C29 C28 C27 1.0(3) . . . . ? C26 C27 C28 C29 0.6(3) . . . . ? C30 C27 C28 C29 -176.72(19) . . . . ? C1 Si1 C7 C8 40.88(19) . . . . ? C17 Si1 C7 C8 159.27(16) . . . . ? C13 Si1 C7 C8 -82.27(18) . . . . ? C1 Si1 C7 C12 -144.49(17) . . . . ? C17 Si1 C7 C12 -26.11(19) . . . . ? C13 Si1 C7 C12 92.35(18) . . . . ? C10 C9 C8 C7 -1.3(3) . . . . ? C12 C7 C8 C9 0.7(3) . . . . ? Si1 C7 C8 C9 175.52(16) . . . . ? C18 N1 C20 C19 20.76(15) . . . . ? S1 N1 C20 C19 156.46(15) . . . . ? C21 C19 C20 N1 -144.90(18) . . . . ? C18 C19 C20 N1 -20.20(14) . . . . ? C2 C1 C6 C5 1.5(3) . . . . ? Si1 C1 C6 C5 178.00(16) . . . . ? C3 C4 C5 C6 -1.0(3) . . . . ? C1 C6 C5 C4 -0.2(3) . . . . ? C19 C21 C22 C23 116.6(2) . . . . ? C8 C9 C10 C11 1.5(3) . . . . ? C9 C10 C11 C12 -1.1(4) . . . . ? C10 C11 C12 C7 0.5(3) . . . . ? C8 C7 C12 C11 -0.2(3) . . . . ? Si1 C7 C12 C11 -175.07(17) . . . . ? C7 Si1 C13 C16 74.82(18) . . . . ? C1 Si1 C13 C16 -46.33(18) . . . . ? C17 Si1 C13 C16 -165.92(16) . . . . ? C7 Si1 C13 C14 -163.02(15) . . . . ? C1 Si1 C13 C14 75.83(17) . . . . ? C17 Si1 C13 C14 -43.76(18) . . . . ? C7 Si1 C13 C15 -43.67(17) . . . . ? C1 Si1 C13 C15 -164.82(14) . . . . ? C17 Si1 C13 C15 75.59(16) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.361 _refine_diff_density_min -0.208 _refine_diff_density_rms 0.046 # Attachment '3c1.cif' data_4augbm _database_code_depnum_ccdc_archive 'CCDC 859593' #TrackingRef '3c1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 'benzyl pyrrolidine' _chemical_melting_point ? _chemical_formula_moiety 'C34 H39 N O2 S Si' _chemical_formula_sum 'C34 H39 N O2 S Si' _chemical_formula_weight 553.81 _chemical_absolute_configuration syn 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 orthorhombic _symmetry_space_group_name_H-M p_21_21_21 _symmetry_space_group_name_HALL 'P 2ac 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 10.1607(7) _cell_length_b 13.0737(10) _cell_length_c 22.9043(17) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3042.6(4) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min 2.2 _cell_measurement_theta_max 25.5 _exptl_crystal_description cuboid _exptl_crystal_colour colorless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.209 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1184 _exptl_absorpt_coefficient_mu 0.176 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_correction_T_min 0.9656 _exptl_absorpt_correction_T_max 0.9740 _exptl_absorpt_process_details '(North et al., 1968)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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-Omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16338 _diffrn_reflns_av_R_equivalents 0.0401 _diffrn_reflns_av_sigmaI/netI 0.0452 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 2.19 _diffrn_reflns_theta_max 25.50 _reflns_number_total 5657 _reflns_number_gt 5230 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART 5.628 (Bruker, 2003)' _computing_cell_refinement 'SMART 5.628 (Bruker, 2003)' _computing_data_reduction 'SAINT+ 6.45 (Bruker, 2003)' _computing_structure_solution Sir92 _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'diamond 3.1d' _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^)+(0.0486P)^2^+0.4278P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.01(7) _refine_ls_number_reflns 5657 _refine_ls_number_parameters 352 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0432 _refine_ls_R_factor_gt 0.0389 _refine_ls_wR_factor_ref 0.0944 _refine_ls_wR_factor_gt 0.0914 _refine_ls_goodness_of_fit_ref 1.063 _refine_ls_restrained_S_all 1.063 _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 Si Si 0.62216(6) 0.19739(4) 0.83877(2) 0.01791(13) Uani 1 1 d . . . S S 1.04917(5) -0.01508(4) 0.77308(3) 0.02932(15) Uani 1 1 d . . . O1 O 1.07696(17) -0.06484(13) 0.71874(8) 0.0413(4) Uani 1 1 d . . . N1 N 0.92510(16) 0.06123(13) 0.76138(8) 0.0231(4) Uani 1 1 d . . . O2 O 1.14779(15) 0.04475(14) 0.80124(8) 0.0414(4) Uani 1 1 d . . . C006 C 0.7027(2) 0.09967(16) 0.61944(9) 0.0216(5) Uani 1 1 d . . . C007 C 0.6312(2) 0.25129(16) 0.96013(9) 0.0240(5) Uani 1 1 d . . . H007 H 0.5586 0.2083 0.9635 0.029 Uiso 1 1 calc R . . C008 C 0.8027(2) 0.01801(16) 0.73783(9) 0.0220(4) Uani 1 1 d . . . H00A H 0.7630 -0.0298 0.7650 0.026 Uiso 1 1 calc R . . H00B H 0.8178 -0.0162 0.7009 0.026 Uiso 1 1 calc R . . C009 C 0.5632(2) 0.06700(15) 0.86233(9) 0.0196(4) Uani 1 1 d . . . C010 C 0.8010(2) 0.32694(16) 0.90283(10) 0.0255(5) Uani 1 1 d . . . H010 H 0.8436 0.3363 0.8673 0.031 Uiso 1 1 calc R . . C011 C 0.9939(2) -0.11078(17) 0.82218(10) 0.0266(5) Uani 1 1 d . . . C012 C 0.4776(2) -0.12554(17) 0.90298(10) 0.0270(5) Uani 1 1 d . . . H012 H 0.4496 -0.1891 0.9163 0.032 Uiso 1 1 calc R . . C013 C 0.8853(2) 0.13373(16) 0.80747(9) 0.0221(4) Uani 1 1 d . . . H01A H 0.9525 0.1852 0.8139 0.027 Uiso 1 1 calc R . . H01B H 0.8681 0.0984 0.8439 0.027 Uiso 1 1 calc R . . C014 C 0.5340(2) 0.02328(17) 0.55926(9) 0.0280(5) Uani 1 1 d . . . H014 H 0.4456 0.0167 0.5495 0.034 Uiso 1 1 calc R . . C015 C 0.6918(2) 0.26233(15) 0.90564(9) 0.0200(4) Uani 1 1 d . . . C016 C 0.6405(2) 0.00672(16) 0.89984(9) 0.0252(5) Uani 1 1 d . . . H016 H 0.7221 0.0313 0.9118 0.030 Uiso 1 1 calc R . . C017 C 0.7960(2) 0.04488(17) 0.58780(9) 0.0273(5) Uani 1 1 d . . . H017 H 0.8848 0.0522 0.5969 0.033 Uiso 1 1 calc R . . C018 C 0.4415(2) 0.02591(15) 0.84610(9) 0.0225(4) Uani 1 1 d . . . H018 H 0.3880 0.0627 0.8207 0.027 Uiso 1 1 calc R . . C019 C 0.7596(2) -0.01991(18) 0.54330(9) 0.0298(5) Uani 1 1 d . . . H019 H 0.8236 -0.0561 0.5230 0.036 Uiso 1 1 calc R . . C020 C 0.75820(19) 0.18219(15) 0.78275(9) 0.0184(4) Uani 1 1 d . . . H020 H 0.7802 0.2501 0.7675 0.022 Uiso 1 1 calc R . . C021 C 0.4314(2) 0.24686(17) 0.74865(9) 0.0271(5) Uani 1 1 d . . . H02A H 0.3932 0.1801 0.7527 0.041 Uiso 1 1 calc R . . H02B H 0.5014 0.2444 0.7206 0.041 Uiso 1 1 calc R . . H02C H 0.3654 0.2942 0.7357 0.041 Uiso 1 1 calc R . . C022 C 0.48601(19) 0.28173(16) 0.80765(9) 0.0219(5) Uani 1 1 d . . . C023 C 0.7430(2) 0.16492(16) 0.67099(9) 0.0213(4) Uani 1 1 d . . . H02D H 0.6946 0.2288 0.6697 0.026 Uiso 1 1 calc R . . H02E H 0.8359 0.1810 0.6677 0.026 Uiso 1 1 calc R . . C024 C 0.9304(2) -0.19597(17) 0.80053(10) 0.0291(5) Uani 1 1 d . . . H024 H 0.9209 -0.2047 0.7604 0.035 Uiso 1 1 calc R . . C025 C 0.9592(3) -0.17143(19) 0.91941(11) 0.0374(6) Uani 1 1 d . . . H025 H 0.9696 -0.1632 0.9595 0.045 Uiso 1 1 calc R . . C026 C 0.5709(2) 0.08769(16) 0.60418(9) 0.0244(5) Uani 1 1 d . . . H026 H 0.5067 0.1236 0.6246 0.029 Uiso 1 1 calc R . . C027 C 0.6762(2) 0.30264(18) 1.00929(10) 0.0299(5) Uani 1 1 d . . . H027 H 0.6334 0.2947 1.0449 0.036 Uiso 1 1 calc R . . C028 C 0.6283(2) -0.03159(17) 0.52859(9) 0.0295(5) Uani 1 1 d . . . H028 H 0.6036 -0.0755 0.4986 0.035 Uiso 1 1 calc R . . C029 C 0.71796(19) 0.11276(15) 0.73009(9) 0.0189(4) Uani 1 1 d . . . H029 H 0.6248 0.0942 0.7334 0.023 Uiso 1 1 calc R . . C030 C 0.3714(2) 0.28876(17) 0.85160(9) 0.0268(5) Uani 1 1 d . . . H03A H 0.4044 0.3107 0.8888 0.040 Uiso 1 1 calc R . . H03B H 0.3308 0.2228 0.8556 0.040 Uiso 1 1 calc R . . H03C H 0.3075 0.3371 0.8377 0.040 Uiso 1 1 calc R . . C031 C 0.8935(2) -0.25745(18) 0.89848(11) 0.0349(6) Uani 1 1 d . . . C032 C 0.3983(2) -0.06793(16) 0.86662(10) 0.0265(5) Uani 1 1 d . . . H032 H 0.3158 -0.0922 0.8559 0.032 Uiso 1 1 calc R . . C033 C 0.5991(2) -0.08760(17) 0.91938(10) 0.0293(5) Uani 1 1 d . . . H033 H 0.6532 -0.1260 0.9437 0.035 Uiso 1 1 calc R . . C034 C 0.8475(2) 0.37762(18) 0.95210(11) 0.0312(5) Uani 1 1 d . . . H034 H 0.9210 0.4197 0.9492 0.037 Uiso 1 1 calc R . . C035 C 0.8807(2) -0.26851(18) 0.83871(11) 0.0334(5) Uani 1 1 d . . . H035 H 0.8380 -0.3258 0.8238 0.040 Uiso 1 1 calc R . . C036 C 1.0093(2) -0.09816(19) 0.88215(10) 0.0321(5) Uani 1 1 d . . . H036 H 1.0527 -0.0411 0.8969 0.039 Uiso 1 1 calc R . . C037 C 0.7853(3) 0.36585(19) 1.00497(11) 0.0337(6) Uani 1 1 d . . . H037 H 0.8163 0.4002 1.0378 0.040 Uiso 1 1 calc R . . C038 C 0.5462(2) 0.38899(16) 0.79918(10) 0.0284(5) Uani 1 1 d . . . H03D H 0.5816 0.4128 0.8356 0.043 Uiso 1 1 calc R . . H03E H 0.4793 0.4354 0.7860 0.043 Uiso 1 1 calc R . . H03F H 0.6153 0.3856 0.7707 0.043 Uiso 1 1 calc R . . C039 C 0.8373(3) -0.3346(2) 0.93940(14) 0.0534(8) Uani 1 1 d . . . H03G H 0.7958 -0.3883 0.9175 0.080 Uiso 1 1 calc R . . H03H H 0.7734 -0.3024 0.9642 0.080 Uiso 1 1 calc R . . H03I H 0.9065 -0.3630 0.9629 0.080 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 Si 0.0184(3) 0.0176(3) 0.0177(3) 0.0001(2) -0.0010(2) 0.0006(2) S 0.0202(3) 0.0327(3) 0.0350(3) 0.0027(3) 0.0033(2) 0.0083(2) O1 0.0413(10) 0.0452(10) 0.0374(10) 0.0023(8) 0.0121(8) 0.0196(8) N1 0.0185(9) 0.0222(9) 0.0286(10) -0.0005(8) 0.0011(7) 0.0012(7) O2 0.0191(8) 0.0421(10) 0.0631(12) 0.0080(9) -0.0052(8) 0.0021(7) C006 0.0264(11) 0.0205(10) 0.0178(10) 0.0025(9) 0.0023(9) -0.0009(9) C007 0.0259(12) 0.0240(11) 0.0222(11) -0.0003(9) -0.0008(9) 0.0005(10) C008 0.0223(11) 0.0215(10) 0.0221(11) 0.0003(9) -0.0005(9) 0.0001(9) C009 0.0219(11) 0.0197(10) 0.0173(10) -0.0038(8) 0.0027(8) -0.0001(9) C010 0.0261(12) 0.0229(11) 0.0276(12) -0.0009(9) 0.0001(9) -0.0014(9) C011 0.0219(11) 0.0277(12) 0.0302(12) 0.0003(10) -0.0015(9) 0.0089(9) C012 0.0362(13) 0.0200(11) 0.0248(11) -0.0019(9) 0.0024(10) -0.0060(9) C013 0.0186(10) 0.0213(10) 0.0264(11) -0.0041(9) 0.0015(9) 0.0004(9) C014 0.0303(12) 0.0292(11) 0.0246(11) 0.0065(10) -0.0084(10) -0.0049(10) C015 0.0228(11) 0.0170(10) 0.0202(11) -0.0006(8) -0.0036(9) 0.0020(8) C016 0.0234(11) 0.0253(11) 0.0268(11) 0.0008(9) -0.0029(9) -0.0025(9) C017 0.0272(12) 0.0312(12) 0.0236(12) 0.0016(10) 0.0020(9) -0.0005(10) C018 0.0234(11) 0.0219(10) 0.0221(10) -0.0033(9) -0.0016(9) 0.0035(9) C019 0.0386(14) 0.0290(12) 0.0218(11) -0.0022(10) 0.0056(10) 0.0029(11) C020 0.0188(10) 0.0171(10) 0.0192(10) 0.0012(8) -0.0008(8) -0.0022(8) C021 0.0241(12) 0.0309(12) 0.0264(12) 0.0012(9) -0.0037(9) 0.0077(10) C022 0.0203(11) 0.0238(11) 0.0217(11) 0.0022(9) -0.0016(8) 0.0043(9) C023 0.0198(11) 0.0191(10) 0.0248(11) 0.0003(9) 0.0006(8) 0.0009(8) C024 0.0295(12) 0.0265(11) 0.0311(12) -0.0035(10) -0.0056(10) 0.0100(10) C025 0.0457(16) 0.0367(14) 0.0299(13) 0.0014(11) -0.0067(11) 0.0111(12) C026 0.0272(11) 0.0241(11) 0.0219(11) 0.0031(9) 0.0027(9) 0.0016(9) C027 0.0375(13) 0.0320(13) 0.0201(11) -0.0037(10) -0.0016(9) 0.0046(11) C028 0.0433(14) 0.0287(12) 0.0166(10) 0.0002(9) 0.0005(10) -0.0060(11) C029 0.0170(10) 0.0186(10) 0.0212(10) -0.0009(9) 0.0019(8) -0.0006(8) C030 0.0240(11) 0.0266(11) 0.0299(12) -0.0031(9) 0.0003(9) 0.0082(10) C031 0.0329(14) 0.0310(13) 0.0408(14) 0.0042(11) -0.0005(11) 0.0100(11) C032 0.0245(12) 0.0250(11) 0.0300(12) -0.0041(10) 0.0003(9) -0.0034(9) C033 0.0328(13) 0.0261(11) 0.0289(12) 0.0037(10) -0.0061(10) 0.0007(10) C034 0.0304(13) 0.0253(12) 0.0380(14) -0.0020(10) -0.0067(10) -0.0034(10) C035 0.0272(12) 0.0271(11) 0.0459(15) -0.0005(11) -0.0061(12) 0.0068(10) C036 0.0333(13) 0.0283(12) 0.0347(13) -0.0018(11) -0.0081(10) 0.0074(10) C037 0.0419(15) 0.0301(12) 0.0290(13) -0.0099(10) -0.0154(11) 0.0065(11) C038 0.0308(12) 0.0244(11) 0.0300(12) 0.0048(10) -0.0011(10) 0.0084(10) C039 0.0572(19) 0.0420(16) 0.0611(19) 0.0191(15) 0.0055(15) 0.0106(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 Si C009 1.886(2) . ? Si C015 1.889(2) . ? Si C020 1.896(2) . ? Si C022 1.907(2) . ? S O2 1.4253(18) . ? S O1 1.4325(18) . ? S N1 1.6299(17) . ? S C011 1.774(2) . ? N1 C008 1.469(3) . ? N1 C013 1.475(3) . ? C006 C017 1.392(3) . ? C006 C026 1.393(3) . ? C006 C023 1.513(3) . ? C007 C027 1.388(3) . ? C007 C015 1.399(3) . ? C007 H007 0.9300 . ? C008 C029 1.519(3) . ? C008 H00A 0.9700 . ? C008 H00B 0.9700 . ? C009 C018 1.398(3) . ? C009 C016 1.406(3) . ? C010 C034 1.391(3) . ? C010 C015 1.396(3) . ? C010 H010 0.9300 . ? C011 C024 1.379(3) . ? C011 C036 1.392(3) . ? C012 C032 1.382(3) . ? C012 C033 1.382(3) . ? C012 H012 0.9300 . ? C013 C020 1.545(3) . ? C013 H01A 0.9700 . ? C013 H01B 0.9700 . ? C014 C026 1.381(3) . ? C014 C028 1.387(3) . ? C014 H014 0.9300 . ? C016 C033 1.378(3) . ? C016 H016 0.9300 . ? C017 C019 1.376(3) . ? C017 H017 0.9300 . ? C018 C032 1.385(3) . ? C018 H018 0.9300 . ? C019 C028 1.384(3) . ? C019 H019 0.9300 . ? C020 C029 1.564(3) . ? C020 H020 0.9800 . ? C021 C022 1.530(3) . ? C021 H02A 0.9600 . ? C021 H02B 0.9600 . ? C021 H02C 0.9600 . ? C022 C030 1.542(3) . ? C022 C038 1.542(3) . ? C023 C029 1.537(3) . ? C023 H02D 0.9700 . ? C023 H02E 0.9700 . ? C024 C035 1.385(3) . ? C024 H024 0.9300 . ? C025 C036 1.380(4) . ? C025 C031 1.393(4) . ? C025 H025 0.9300 . ? C026 H026 0.9300 . ? C027 C037 1.386(4) . ? C027 H027 0.9300 . ? C028 H028 0.9300 . ? C029 H029 0.9800 . ? C030 H03A 0.9600 . ? C030 H03B 0.9600 . ? C030 H03C 0.9600 . ? C031 C035 1.383(3) . ? C031 C039 1.491(4) . ? C032 H032 0.9300 . ? C033 H033 0.9300 . ? C034 C037 1.374(4) . ? C034 H034 0.9300 . ? C035 H035 0.9300 . ? C036 H036 0.9300 . ? C037 H037 0.9300 . ? C038 H03D 0.9600 . ? C038 H03E 0.9600 . ? C038 H03F 0.9600 . ? C039 H03G 0.9600 . ? C039 H03H 0.9600 . ? C039 H03I 0.9600 . ? 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 C009 Si C015 107.06(9) . . ? C009 Si C020 109.31(9) . . ? C015 Si C020 108.83(9) . . ? C009 Si C022 113.51(10) . . ? C015 Si C022 108.35(9) . . ? C020 Si C022 109.66(9) . . ? O2 S O1 120.25(11) . . ? O2 S N1 106.39(10) . . ? O1 S N1 106.71(10) . . ? O2 S C011 108.84(11) . . ? O1 S C011 107.04(11) . . ? N1 S C011 106.93(10) . . ? C008 N1 C013 106.13(15) . . ? C008 N1 S 118.67(14) . . ? C013 N1 S 119.19(14) . . ? C017 C006 C026 117.8(2) . . ? C017 C006 C023 120.82(19) . . ? C026 C006 C023 121.28(19) . . ? C027 C007 C015 121.9(2) . . ? C027 C007 H007 119.0 . . ? C015 C007 H007 119.0 . . ? N1 C008 C029 102.07(16) . . ? N1 C008 H00A 111.4 . . ? C029 C008 H00A 111.4 . . ? N1 C008 H00B 111.4 . . ? C029 C008 H00B 111.4 . . ? H00A C008 H00B 109.2 . . ? C018 C009 C016 116.19(18) . . ? C018 C009 Si 123.53(16) . . ? C016 C009 Si 120.25(16) . . ? C034 C010 C015 121.4(2) . . ? C034 C010 H010 119.3 . . ? C015 C010 H010 119.3 . . ? C024 C011 C036 120.2(2) . . ? C024 C011 S 119.32(18) . . ? C036 C011 S 120.42(19) . . ? C032 C012 C033 119.3(2) . . ? C032 C012 H012 120.4 . . ? C033 C012 H012 120.4 . . ? N1 C013 C020 103.32(16) . . ? N1 C013 H01A 111.1 . . ? C020 C013 H01A 111.1 . . ? N1 C013 H01B 111.1 . . ? C020 C013 H01B 111.1 . . ? H01A C013 H01B 109.1 . . ? C026 C014 C028 120.3(2) . . ? C026 C014 H014 119.8 . . ? C028 C014 H014 119.8 . . ? C010 C015 C007 116.95(19) . . ? C010 C015 Si 122.17(16) . . ? C007 C015 Si 120.81(16) . . ? C033 C016 C009 122.0(2) . . ? C033 C016 H016 119.0 . . ? C009 C016 H016 119.0 . . ? C019 C017 C006 121.3(2) . . ? C019 C017 H017 119.4 . . ? C006 C017 H017 119.4 . . ? C032 C018 C009 122.0(2) . . ? C032 C018 H018 119.0 . . ? C009 C018 H018 119.0 . . ? C017 C019 C028 120.5(2) . . ? C017 C019 H019 119.7 . . ? C028 C019 H019 119.7 . . ? C013 C020 C029 105.25(16) . . ? C013 C020 Si 113.83(14) . . ? C029 C020 Si 113.08(13) . . ? C013 C020 H020 108.1 . . ? C029 C020 H020 108.1 . . ? Si C020 H020 108.1 . . ? C022 C021 H02A 109.5 . . ? C022 C021 H02B 109.5 . . ? H02A C021 H02B 109.5 . . ? C022 C021 H02C 109.5 . . ? H02A C021 H02C 109.5 . . ? H02B C021 H02C 109.5 . . ? C021 C022 C030 108.69(17) . . ? C021 C022 C038 107.68(17) . . ? C030 C022 C038 109.12(18) . . ? C021 C022 Si 114.88(14) . . ? C030 C022 Si 109.77(14) . . ? C038 C022 Si 106.55(14) . . ? C006 C023 C029 113.10(17) . . ? C006 C023 H02D 109.0 . . ? C029 C023 H02D 109.0 . . ? C006 C023 H02E 109.0 . . ? C029 C023 H02E 109.0 . . ? H02D C023 H02E 107.8 . . ? C011 C024 C035 119.8(2) . . ? C011 C024 H024 120.1 . . ? C035 C024 H024 120.1 . . ? C036 C025 C031 121.6(2) . . ? C036 C025 H025 119.2 . . ? C031 C025 H025 119.2 . . ? C014 C026 C006 121.1(2) . . ? C014 C026 H026 119.5 . . ? C006 C026 H026 119.5 . . ? C037 C027 C007 119.6(2) . . ? C037 C027 H027 120.2 . . ? C007 C027 H027 120.2 . . ? C019 C028 C014 119.0(2) . . ? C019 C028 H028 120.5 . . ? C014 C028 H028 120.5 . . ? C008 C029 C023 111.76(17) . . ? C008 C029 C020 103.60(16) . . ? C023 C029 C020 112.24(16) . . ? C008 C029 H029 109.7 . . ? C023 C029 H029 109.7 . . ? C020 C029 H029 109.7 . . ? C022 C030 H03A 109.5 . . ? C022 C030 H03B 109.5 . . ? H03A C030 H03B 109.5 . . ? C022 C030 H03C 109.5 . . ? H03A C030 H03C 109.5 . . ? H03B C030 H03C 109.5 . . ? C035 C031 C025 118.0(2) . . ? C035 C031 C039 121.1(2) . . ? C025 C031 C039 120.9(2) . . ? C012 C032 C018 120.2(2) . . ? C012 C032 H032 119.9 . . ? C018 C032 H032 119.9 . . ? C016 C033 C012 120.4(2) . . ? C016 C033 H033 119.8 . . ? C012 C033 H033 119.8 . . ? C037 C034 C010 120.4(2) . . ? C037 C034 H034 119.8 . . ? C010 C034 H034 119.8 . . ? C031 C035 C024 121.3(2) . . ? C031 C035 H035 119.4 . . ? C024 C035 H035 119.4 . . ? C025 C036 C011 119.1(2) . . ? C025 C036 H036 120.4 . . ? C011 C036 H036 120.4 . . ? C034 C037 C027 119.8(2) . . ? C034 C037 H037 120.1 . . ? C027 C037 H037 120.1 . . ? C022 C038 H03D 109.5 . . ? C022 C038 H03E 109.5 . . ? H03D C038 H03E 109.5 . . ? C022 C038 H03F 109.5 . . ? H03D C038 H03F 109.5 . . ? H03E C038 H03F 109.5 . . ? C031 C039 H03G 109.5 . . ? C031 C039 H03H 109.5 . . ? H03G C039 H03H 109.5 . . ? C031 C039 H03I 109.5 . . ? H03G C039 H03I 109.5 . . ? H03H C039 H03I 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O2 S N1 C008 -174.06(16) . . . . ? O1 S N1 C008 56.40(18) . . . . ? C011 S N1 C008 -57.87(18) . . . . ? O2 S N1 C013 -42.13(18) . . . . ? O1 S N1 C013 -171.67(15) . . . . ? C011 S N1 C013 74.06(17) . . . . ? C013 N1 C008 C029 45.88(19) . . . . ? S N1 C008 C029 -176.66(14) . . . . ? C015 Si C009 C018 134.40(17) . . . . ? C020 Si C009 C018 -107.88(18) . . . . ? C022 Si C009 C018 14.9(2) . . . . ? C015 Si C009 C016 -43.34(19) . . . . ? C020 Si C009 C016 74.39(18) . . . . ? C022 Si C009 C016 -162.85(16) . . . . ? O2 S C011 C024 -160.22(17) . . . . ? O1 S C011 C024 -28.8(2) . . . . ? N1 S C011 C024 85.23(19) . . . . ? O2 S C011 C036 22.5(2) . . . . ? O1 S C011 C036 153.92(18) . . . . ? N1 S C011 C036 -92.03(19) . . . . ? C008 N1 C013 C020 -36.84(19) . . . . ? S N1 C013 C020 -174.03(13) . . . . ? C034 C010 C015 C007 0.2(3) . . . . ? C034 C010 C015 Si 177.17(17) . . . . ? C027 C007 C015 C010 0.5(3) . . . . ? C027 C007 C015 Si -176.44(17) . . . . ? C009 Si C015 C010 144.23(17) . . . . ? C020 Si C015 C010 26.2(2) . . . . ? C022 Si C015 C010 -92.99(18) . . . . ? C009 Si C015 C007 -38.94(19) . . . . ? C020 Si C015 C007 -156.98(17) . . . . ? C022 Si C015 C007 83.84(18) . . . . ? C018 C009 C016 C033 0.2(3) . . . . ? Si C009 C016 C033 178.07(17) . . . . ? C026 C006 C017 C019 -0.7(3) . . . . ? C023 C006 C017 C019 175.7(2) . . . . ? C016 C009 C018 C032 1.2(3) . . . . ? Si C009 C018 C032 -176.61(16) . . . . ? C006 C017 C019 C028 0.5(3) . . . . ? N1 C013 C020 C029 13.32(19) . . . . ? N1 C013 C020 Si 137.69(14) . . . . ? C009 Si C020 C013 -66.57(16) . . . . ? C015 Si C020 C013 50.04(16) . . . . ? C022 Si C020 C013 168.40(14) . . . . ? C009 Si C020 C029 53.49(16) . . . . ? C015 Si C020 C029 170.09(13) . . . . ? C022 Si C020 C029 -71.54(16) . . . . ? C009 Si C022 C021 -68.88(17) . . . . ? C015 Si C022 C021 172.34(15) . . . . ? C020 Si C022 C021 53.68(17) . . . . ? C009 Si C022 C030 53.94(17) . . . . ? C015 Si C022 C030 -64.83(16) . . . . ? C020 Si C022 C030 176.51(14) . . . . ? C009 Si C022 C038 171.97(14) . . . . ? C015 Si C022 C038 53.20(16) . . . . ? C020 Si C022 C038 -65.46(16) . . . . ? C017 C006 C023 C029 -100.4(2) . . . . ? C026 C006 C023 C029 75.9(2) . . . . ? C036 C011 C024 C035 0.7(3) . . . . ? S C011 C024 C035 -176.60(16) . . . . ? C028 C014 C026 C006 0.5(3) . . . . ? C017 C006 C026 C014 0.2(3) . . . . ? C023 C006 C026 C014 -176.13(19) . . . . ? C015 C007 C027 C037 -0.9(3) . . . . ? C017 C019 C028 C014 0.2(3) . . . . ? C026 C014 C028 C019 -0.7(3) . . . . ? N1 C008 C029 C023 85.90(19) . . . . ? N1 C008 C029 C020 -35.15(19) . . . . ? C006 C023 C029 C008 65.0(2) . . . . ? C006 C023 C029 C020 -179.10(17) . . . . ? C013 C020 C029 C008 13.4(2) . . . . ? Si C020 C029 C008 -111.49(15) . . . . ? C013 C020 C029 C023 -107.37(18) . . . . ? Si C020 C029 C023 127.78(15) . . . . ? C036 C025 C031 C035 0.8(4) . . . . ? C036 C025 C031 C039 -178.6(2) . . . . ? C033 C012 C032 C018 1.2(3) . . . . ? C009 C018 C032 C012 -1.9(3) . . . . ? C009 C016 C033 C012 -0.9(3) . . . . ? C032 C012 C033 C016 0.2(3) . . . . ? C015 C010 C034 C037 -0.7(3) . . . . ? C025 C031 C035 C024 -0.7(3) . . . . ? C039 C031 C035 C024 178.7(2) . . . . ? C011 C024 C035 C031 0.0(3) . . . . ? C031 C025 C036 C011 -0.2(4) . . . . ? C024 C011 C036 C025 -0.6(3) . . . . ? S C011 C036 C025 176.66(17) . . . . ? C010 C034 C037 C027 0.4(4) . . . . ? C007 C027 C037 C034 0.4(3) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.332 _refine_diff_density_min -0.204 _refine_diff_density_rms 0.049 # Attachment '3c2.cif' data_20sepam _database_code_depnum_ccdc_archive 'CCDC 859594' #TrackingRef '3c2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C34 H39 N O2 S Si' _chemical_formula_sum 'C34 H39 N O2 S Si' _chemical_formula_weight 553.82 _chemical_absolute_configuration rmad 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 orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' _symmetry_space_group_name_HALL 'P 2ac 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 10.158(5) _cell_length_b 13.071(5) _cell_length_c 22.898(5) _cell_angle_alpha 90.000(5) _cell_angle_beta 90.000(5) _cell_angle_gamma 90.000(5) _cell_volume 3040(2) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min 2.4 _cell_measurement_theta_max 26 _exptl_crystal_description blocks _exptl_crystal_colour colorless _exptl_crystal_size_max 0.11 _exptl_crystal_size_mid 0.09 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.210 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1184.0 _exptl_absorpt_coefficient_mu 0.177 _exptl_absorpt_correction_type PSI-SCAN _exptl_absorpt_correction_T_min 0.455436 _exptl_absorpt_correction_T_max 1 _exptl_absorpt_process_details '(North et al., 1968)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71069 _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-Omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16416 _diffrn_reflns_av_R_equivalents 0.0771 _diffrn_reflns_av_sigmaI/netI 0.0923 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 2.36 _diffrn_reflns_theta_max 25.50 _reflns_number_total 5637 _reflns_number_gt 4384 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART 5.628 (Bruker, 2003)' _computing_cell_refinement 'SMART 5.628 (Bruker, 2003)' _computing_data_reduction 'SAINT+ 6.45 (Bruker, 2003)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'DIAMOND 3.1d' _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^)+(0.0444P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.08(10) _refine_ls_number_reflns 5637 _refine_ls_number_parameters 356 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0744 _refine_ls_R_factor_gt 0.0545 _refine_ls_wR_factor_ref 0.1213 _refine_ls_wR_factor_gt 0.1093 _refine_ls_goodness_of_fit_ref 1.010 _refine_ls_restrained_S_all 1.010 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Si1 Si 0.87777(10) 0.80249(7) 0.66127(4) 0.0209(2) Uani 1 1 d . . . S1 S 0.45088(9) 1.01514(7) 0.72689(4) 0.0325(2) Uani 1 1 d . . . O1 O 0.3519(2) 0.9551(2) 0.69873(12) 0.0436(7) Uani 1 1 d . . . O2 O 0.4230(3) 1.06457(19) 0.78134(11) 0.0436(7) Uani 1 1 d . . . N1 N 0.5743(3) 0.9387(2) 0.73846(12) 0.0257(7) Uani 1 1 d . . . C1 C 0.6968(3) 0.9822(2) 0.76223(14) 0.0241(8) Uani 1 1 d . . . H1A H 0.6814 1.0163 0.7992 0.029 Uiso 1 1 calc R . . H1B H 0.7365 1.0302 0.7351 0.029 Uiso 1 1 calc R . . C2 C 0.7821(3) 0.8872(2) 0.76992(14) 0.0213(7) Uani 1 1 d . . . H2 H 0.8752 0.9061 0.7667 0.026 Uiso 1 1 calc R . . C3 C 0.7424(3) 0.8184(2) 0.71702(14) 0.0206(7) Uani 1 1 d . . . H3 H 0.7203 0.7505 0.7322 0.025 Uiso 1 1 calc R . . C4 C 0.6145(3) 0.8667(2) 0.69242(14) 0.0234(8) Uani 1 1 d . . . H4A H 0.6314 0.9022 0.6560 0.028 Uiso 1 1 calc R . . H4B H 0.5475 0.8150 0.6860 0.028 Uiso 1 1 calc R . . C5 C 0.7575(3) 0.8350(2) 0.82909(14) 0.0243(8) Uani 1 1 d . . . H5A H 0.6647 0.8185 0.8324 0.029 Uiso 1 1 calc R . . H5B H 0.8065 0.7713 0.8304 0.029 Uiso 1 1 calc R . . C6 C 0.7974(4) 0.9005(3) 0.88072(14) 0.0241(8) Uani 1 1 d . . . C7 C 0.7040(4) 0.9550(3) 0.91221(14) 0.0298(9) Uani 1 1 d . . . H7 H 0.6153 0.9478 0.9030 0.036 Uiso 1 1 calc R . . C8 C 0.7407(4) 1.0197(3) 0.95687(15) 0.0319(9) Uani 1 1 d . . . H8 H 0.6767 1.0556 0.9774 0.038 Uiso 1 1 calc R . . C9 C 0.8720(4) 1.0316(3) 0.97130(15) 0.0331(9) Uani 1 1 d . . . H9 H 0.8966 1.0756 1.0013 0.040 Uiso 1 1 calc R . . C10 C 0.9664(4) 0.9773(3) 0.94059(15) 0.0302(9) Uani 1 1 d . . . H10 H 1.0549 0.9843 0.9502 0.036 Uiso 1 1 calc R . . C11 C 0.9291(4) 0.9126(2) 0.89564(14) 0.0265(8) Uani 1 1 d . . . H11 H 0.9931 0.8767 0.8751 0.032 Uiso 1 1 calc R . . C12 C 0.5059(3) 1.1110(3) 0.67778(15) 0.0284(9) Uani 1 1 d . . . C13 C 0.5696(4) 1.1960(3) 0.69953(15) 0.0299(8) Uani 1 1 d . . . H13 H 0.5794 1.2047 0.7396 0.036 Uiso 1 1 calc R . . C14 C 0.6189(4) 1.2680(3) 0.66124(17) 0.0362(9) Uani 1 1 d . . . H14 H 0.6614 1.3255 0.6761 0.043 Uiso 1 1 calc R . . C15 C 0.6068(4) 1.2572(3) 0.60159(17) 0.0375(10) Uani 1 1 d . . . C16 C 0.5404(4) 1.1712(3) 0.58037(16) 0.0389(10) Uani 1 1 d . . . H16 H 0.5298 1.1630 0.5403 0.047 Uiso 1 1 calc R . . C17 C 0.4905(4) 1.0986(3) 0.61769(16) 0.0344(10) Uani 1 1 d . . . H17 H 0.4469 1.0416 0.6030 0.041 Uiso 1 1 calc R . . C18 C 0.6628(5) 1.3349(3) 0.56072(19) 0.0542(13) Uani 1 1 d . . . H18A H 0.6923 1.3933 0.5825 0.081 Uiso 1 1 calc R . . H18B H 0.5963 1.3558 0.5334 0.081 Uiso 1 1 calc R . . H18C H 0.7358 1.3056 0.5400 0.081 Uiso 1 1 calc R . . C19 C 0.9371(3) 0.9327(2) 0.63759(14) 0.0216(8) Uani 1 1 d . . . C20 C 1.0581(3) 0.9740(2) 0.65388(14) 0.0245(8) Uani 1 1 d . . . H20 H 1.1115 0.9374 0.6794 0.029 Uiso 1 1 calc R . . C21 C 1.1015(4) 1.0679(2) 0.63330(15) 0.0279(8) Uani 1 1 d . . . H21 H 1.1840 1.0921 0.6441 0.033 Uiso 1 1 calc R . . C22 C 1.0226(4) 1.1255(3) 0.59690(15) 0.0289(9) Uani 1 1 d . . . H22 H 1.0508 1.1890 0.5836 0.035 Uiso 1 1 calc R . . C23 C 0.9010(4) 1.0875(3) 0.58049(15) 0.0324(9) Uani 1 1 d . . . H23 H 0.8471 1.1259 0.5560 0.039 Uiso 1 1 calc R . . C24 C 0.8588(4) 0.9930(2) 0.60018(14) 0.0263(8) Uani 1 1 d . . . H24 H 0.7769 0.9686 0.5885 0.032 Uiso 1 1 calc R . . C25 C 0.8084(3) 0.7379(2) 0.59432(14) 0.0205(8) Uani 1 1 d . . . C26 C 0.8687(4) 0.7485(2) 0.54007(14) 0.0255(8) Uani 1 1 d . . . H26 H 0.9417 0.7911 0.5368 0.031 Uiso 1 1 calc R . . C27 C 0.8239(4) 0.6978(3) 0.49079(15) 0.0326(9) Uani 1 1 d . . . H27 H 0.8666 0.7061 0.4552 0.039 Uiso 1 1 calc R . . C28 C 0.7145(4) 0.6345(3) 0.49511(16) 0.0340(10) Uani 1 1 d . . . H28 H 0.6828 0.6007 0.4623 0.041 Uiso 1 1 calc R . . C29 C 0.6537(4) 0.6223(3) 0.54778(16) 0.0329(9) Uani 1 1 d . . . H29 H 0.5808 0.5796 0.5506 0.039 Uiso 1 1 calc R . . C30 C 0.6991(4) 0.6726(3) 0.59717(16) 0.0297(9) Uani 1 1 d . . . H30 H 0.6564 0.6629 0.6327 0.036 Uiso 1 1 calc R . . C31 C 1.0137(3) 0.7182(2) 0.69236(14) 0.0225(8) Uani 1 1 d . . . C32 C 0.9540(4) 0.6113(2) 0.70085(15) 0.0312(9) Uani 1 1 d . . . H32A H 1.0196 0.5661 0.7166 0.047 Uiso 1 1 calc R . . H32B H 0.9241 0.5855 0.6639 0.047 Uiso 1 1 calc R . . H32C H 0.8810 0.6155 0.7274 0.047 Uiso 1 1 calc R . . C33 C 1.1284(4) 0.7113(3) 0.64871(14) 0.0308(9) Uani 1 1 d . . . H33A H 1.1902 0.6606 0.6618 0.046 Uiso 1 1 calc R . . H33B H 1.1715 0.7765 0.6461 0.046 Uiso 1 1 calc R . . H33C H 1.0951 0.6924 0.6110 0.046 Uiso 1 1 calc R . . C34 C 1.0690(4) 0.7533(3) 0.75134(14) 0.0289(9) Uani 1 1 d . . . H34A H 0.9992 0.7557 0.7796 0.043 Uiso 1 1 calc R . . H34B H 1.1071 0.8201 0.7472 0.043 Uiso 1 1 calc R . . H34C H 1.1352 0.7059 0.7642 0.043 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Si1 0.0226(5) 0.0194(5) 0.0209(5) 0.0006(4) -0.0011(4) 0.0010(4) S1 0.0247(5) 0.0342(5) 0.0384(5) 0.0024(4) 0.0032(4) 0.0083(4) O1 0.0223(15) 0.0433(16) 0.0652(19) 0.0075(14) -0.0068(13) 0.0007(13) O2 0.0443(18) 0.0461(16) 0.0405(16) 0.0032(13) 0.0141(13) 0.0229(14) N1 0.0218(17) 0.0223(14) 0.0329(17) 0.0007(12) -0.0001(13) -0.0019(13) C1 0.024(2) 0.0221(17) 0.0257(19) 0.0007(15) 0.0011(15) -0.0012(16) C2 0.0186(18) 0.0201(17) 0.0252(18) -0.0016(15) 0.0012(15) -0.0010(15) C3 0.0219(19) 0.0178(17) 0.0222(18) 0.0018(14) -0.0044(14) -0.0023(15) C4 0.0216(19) 0.0229(17) 0.0256(19) -0.0037(14) 0.0018(16) 0.0000(16) C5 0.023(2) 0.0206(17) 0.029(2) 0.0014(15) -0.0017(15) -0.0001(15) C6 0.029(2) 0.0199(18) 0.0238(19) 0.0036(14) 0.0039(16) -0.0019(17) C7 0.029(2) 0.034(2) 0.027(2) -0.0006(16) 0.0004(16) -0.0015(18) C8 0.043(2) 0.026(2) 0.026(2) -0.0030(16) 0.0055(17) 0.0025(19) C9 0.045(2) 0.031(2) 0.0224(19) 0.0007(15) 0.0014(19) -0.004(2) C10 0.033(2) 0.0309(19) 0.0270(19) 0.0065(17) -0.0115(17) -0.0052(18) C11 0.031(2) 0.0248(19) 0.0231(19) 0.0025(15) 0.0014(16) 0.0050(17) C12 0.025(2) 0.030(2) 0.030(2) 0.0004(16) -0.0020(16) 0.0091(17) C13 0.034(2) 0.0271(19) 0.0285(19) -0.0025(16) -0.0043(17) 0.0070(19) C14 0.027(2) 0.032(2) 0.050(3) -0.0038(18) -0.007(2) 0.0067(18) C15 0.034(2) 0.035(2) 0.044(3) 0.0029(18) 0.002(2) 0.010(2) C16 0.048(3) 0.035(2) 0.034(2) -0.0003(17) -0.007(2) 0.008(2) C17 0.033(2) 0.028(2) 0.042(2) -0.0032(17) -0.0079(18) 0.0067(18) C18 0.059(3) 0.046(3) 0.057(3) 0.020(2) 0.006(2) 0.009(2) C19 0.024(2) 0.0196(17) 0.0209(18) -0.0047(14) 0.0008(15) -0.0003(16) C20 0.0259(19) 0.0238(17) 0.0238(18) -0.0030(15) -0.0017(15) 0.0050(17) C21 0.027(2) 0.0260(19) 0.031(2) -0.0021(16) 0.0009(17) -0.0028(17) C22 0.036(2) 0.0229(18) 0.028(2) 0.0007(16) 0.0013(17) -0.0071(17) C23 0.037(2) 0.027(2) 0.034(2) 0.0063(16) -0.0066(18) 0.0003(18) C24 0.026(2) 0.0261(19) 0.0266(18) 0.0007(15) -0.0037(16) -0.0037(17) C25 0.024(2) 0.0151(16) 0.0225(19) 0.0027(14) -0.0035(15) 0.0043(15) C26 0.027(2) 0.0227(18) 0.0271(19) -0.0013(15) -0.0002(17) -0.0003(17) C27 0.042(2) 0.033(2) 0.0233(19) -0.0054(17) -0.0010(16) 0.002(2) C28 0.044(3) 0.027(2) 0.030(2) -0.0071(16) -0.0126(19) 0.0092(19) C29 0.029(2) 0.027(2) 0.042(2) -0.0033(17) -0.0088(18) -0.0034(18) C30 0.032(2) 0.0257(19) 0.031(2) 0.0011(16) -0.0023(18) -0.0010(17) C31 0.0216(19) 0.0213(17) 0.0246(19) 0.0016(15) 0.0001(15) 0.0034(15) C32 0.031(2) 0.029(2) 0.034(2) 0.0037(16) -0.0045(18) 0.0099(19) C33 0.029(2) 0.0281(19) 0.035(2) -0.0012(16) -0.0027(18) 0.0103(18) C34 0.029(2) 0.0298(19) 0.028(2) 0.0005(15) -0.0033(16) 0.0105(18) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Si1 C19 1.885(3) . ? Si1 C25 1.887(3) . ? Si1 C3 1.888(3) . ? Si1 C31 1.905(3) . ? S1 O1 1.429(3) . ? S1 O2 1.432(3) . ? S1 N1 1.625(3) . ? S1 C12 1.774(4) . ? N1 C4 1.471(4) . ? N1 C1 1.472(4) . ? C1 C2 1.524(4) . ? C2 C5 1.538(4) . ? C2 C3 1.561(4) . ? C3 C4 1.550(5) . ? C5 C6 1.515(5) . ? C6 C11 1.389(5) . ? C6 C7 1.389(5) . ? C7 C8 1.378(5) . ? C8 C9 1.383(5) . ? C9 C10 1.385(5) . ? C10 C11 1.385(5) . ? C12 C13 1.379(5) . ? C12 C17 1.394(5) . ? C13 C14 1.381(5) . ? C14 C15 1.379(5) . ? C15 C16 1.397(5) . ? C15 C18 1.494(5) . ? C16 C17 1.374(5) . ? C19 C20 1.393(5) . ? C19 C24 1.409(4) . ? C20 C21 1.387(4) . ? C21 C22 1.379(5) . ? C22 C23 1.383(5) . ? C23 C24 1.383(5) . ? C25 C26 1.392(4) . ? C25 C30 1.402(5) . ? C26 C27 1.385(4) . ? C27 C28 1.389(5) . ? C28 C29 1.364(5) . ? C29 C30 1.387(5) . ? C31 C34 1.533(4) . ? C31 C32 1.536(5) . ? C31 C33 1.537(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 C19 Si1 C25 106.84(14) . . ? C19 Si1 C3 109.13(14) . . ? C25 Si1 C3 109.08(15) . . ? C19 Si1 C31 113.45(15) . . ? C25 Si1 C31 108.41(14) . . ? C3 Si1 C31 109.83(14) . . ? O1 S1 O2 120.10(17) . . ? O1 S1 N1 106.18(15) . . ? O2 S1 N1 106.73(16) . . ? O1 S1 C12 108.87(17) . . ? O2 S1 C12 107.17(16) . . ? N1 S1 C12 107.14(16) . . ? C4 N1 C1 106.1(3) . . ? C4 N1 S1 119.4(2) . . ? C1 N1 S1 118.4(2) . . ? N1 C1 C2 102.0(2) . . ? C1 C2 C5 111.8(3) . . ? C1 C2 C3 103.5(3) . . ? C5 C2 C3 112.7(3) . . ? C4 C3 C2 105.3(2) . . ? C4 C3 Si1 114.2(2) . . ? C2 C3 Si1 113.6(2) . . ? N1 C4 C3 103.4(3) . . ? C6 C5 C2 113.1(3) . . ? C11 C6 C7 118.1(3) . . ? C11 C6 C5 120.9(3) . . ? C7 C6 C5 120.9(3) . . ? C8 C7 C6 121.0(4) . . ? C7 C8 C9 120.5(3) . . ? C8 C9 C10 119.3(3) . . ? C11 C10 C9 120.0(4) . . ? C10 C11 C6 121.1(3) . . ? C13 C12 C17 120.2(3) . . ? C13 C12 S1 119.2(3) . . ? C17 C12 S1 120.5(3) . . ? C12 C13 C14 119.4(3) . . ? C15 C14 C13 121.8(4) . . ? C14 C15 C16 118.1(4) . . ? C14 C15 C18 121.1(4) . . ? C16 C15 C18 120.9(4) . . ? C17 C16 C15 121.1(4) . . ? C16 C17 C12 119.5(4) . . ? C20 C19 C24 116.4(3) . . ? C20 C19 Si1 123.7(3) . . ? C24 C19 Si1 119.9(3) . . ? C21 C20 C19 122.2(3) . . ? C22 C21 C20 120.2(3) . . ? C21 C22 C23 119.1(3) . . ? C22 C23 C24 120.6(3) . . ? C23 C24 C19 121.5(3) . . ? C26 C25 C30 116.8(3) . . ? C26 C25 Si1 121.1(3) . . ? C30 C25 Si1 122.0(3) . . ? C27 C26 C25 122.3(3) . . ? C26 C27 C28 119.3(3) . . ? C29 C28 C27 119.7(3) . . ? C28 C29 C30 121.0(4) . . ? C29 C30 C25 120.9(3) . . ? C34 C31 C32 107.8(3) . . ? C34 C31 C33 108.2(3) . . ? C32 C31 C33 109.1(3) . . ? C34 C31 Si1 115.0(2) . . ? C32 C31 Si1 106.7(2) . . ? C33 C31 Si1 109.9(2) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.428 _refine_diff_density_min -0.257 _refine_diff_density_rms 0.055 # Attachment '3e1.cif' data_10novb _database_code_depnum_ccdc_archive 'CCDC 859595' #TrackingRef '3e1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 4-flurophenylpyrrolidine _chemical_melting_point ? _chemical_formula_moiety 'C33 H36 F N O2 S Si' _chemical_formula_sum 'C33 H36 F N O2 S Si' _chemical_formula_weight 557.78 _chemical_absolute_configuration rmad 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' F F 0.0171 0.0103 '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 Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) _symmetry_space_group_name_HALL 'P 2ac 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 9.969(5) _cell_length_b 10.025(5) _cell_length_c 29.109(5) _cell_angle_alpha 90.000(5) _cell_angle_beta 90.000(5) _cell_angle_gamma 90.000(5) _cell_volume 2909(2) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3013 _cell_measurement_theta_min 2.47 _cell_measurement_theta_max 21.59 _exptl_crystal_description hexagonal _exptl_crystal_colour colorless _exptl_crystal_size_max 0.102 _exptl_crystal_size_mid 0.079 _exptl_crystal_size_min 0.045 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.274 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1184 _exptl_absorpt_coefficient_mu 0.190 _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 293(2) _diffrn_radiation_wavelength 0.71069 _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 16113 _diffrn_reflns_av_R_equivalents 0.0580 _diffrn_reflns_av_sigmaI/netI 0.0715 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -35 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.15 _diffrn_reflns_theta_max 26.00 _reflns_number_total 5701 _reflns_number_gt 4788 _reflns_threshold_expression >2sigma(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, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0543P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.00(9) _refine_ls_number_reflns 5701 _refine_ls_number_parameters 352 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0607 _refine_ls_R_factor_gt 0.0474 _refine_ls_wR_factor_ref 0.1125 _refine_ls_wR_factor_gt 0.1039 _refine_ls_goodness_of_fit_ref 1.015 _refine_ls_restrained_S_all 1.015 _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 0.1599(3) 1.1073(3) 0.57758(9) 0.0226(6) Uani 1 1 d . . . C2 C 0.2824(3) 1.1652(3) 0.56392(10) 0.0283(7) Uani 1 1 d . . . H2 H 0.3619 1.1205 0.5704 0.034 Uiso 1 1 calc R . . C3 C 0.2885(4) 1.2864(3) 0.54113(11) 0.0360(8) Uani 1 1 d . . . H3 H 0.3711 1.3214 0.5324 0.043 Uiso 1 1 calc R . . C4 C 0.1719(4) 1.3552(3) 0.53133(11) 0.0371(8) Uani 1 1 d . . . H4 H 0.1755 1.4358 0.5155 0.045 Uiso 1 1 calc R . . C5 C 0.0500(4) 1.3036(3) 0.54516(11) 0.0363(8) Uani 1 1 d . . . H5 H -0.0287 1.3500 0.5389 0.044 Uiso 1 1 calc R . . C6 C 0.0447(3) 1.1844(3) 0.56805(10) 0.0292(7) Uani 1 1 d . . . H6 H -0.0384 1.1529 0.5777 0.035 Uiso 1 1 calc R . . C7 C -0.0299(3) 0.8901(3) 0.61521(10) 0.0223(6) Uani 1 1 d . . . C8 C -0.1224(3) 0.9002(3) 0.57895(10) 0.0260(7) Uani 1 1 d . . . H8 H -0.0944 0.9358 0.5511 0.031 Uiso 1 1 calc R . . C9 C -0.2543(3) 0.8584(3) 0.58363(10) 0.0270(7) Uani 1 1 d . . . H9 H -0.3138 0.8673 0.5592 0.032 Uiso 1 1 calc R . . C10 C -0.2974(3) 0.8036(3) 0.62450(10) 0.0269(7) Uani 1 1 d . . . H10 H -0.3858 0.7756 0.6278 0.032 Uiso 1 1 calc R . . C11 C -0.2089(3) 0.7906(3) 0.66031(11) 0.0303(7) Uani 1 1 d . . . H11 H -0.2376 0.7530 0.6878 0.036 Uiso 1 1 calc R . . C12 C -0.0774(3) 0.8328(3) 0.65590(10) 0.0262(7) Uani 1 1 d . . . H12 H -0.0191 0.8229 0.6806 0.031 Uiso 1 1 calc R . . C13 C 0.0827(3) 1.0382(3) 0.73895(10) 0.0215(6) Uani 1 1 d . . . C14 C -0.0522(3) 1.0681(3) 0.74604(10) 0.0249(7) Uani 1 1 d . . . H14 H -0.0986 1.1174 0.7241 0.030 Uiso 1 1 calc R . . C15 C -0.1183(3) 1.0257(3) 0.78518(10) 0.0267(7) Uani 1 1 d . . . H15 H -0.2084 1.0460 0.7897 0.032 Uiso 1 1 calc R . . C16 C -0.0489(3) 0.9534(3) 0.81712(10) 0.0244(6) Uani 1 1 d . . . C17 C 0.0846(3) 0.9216(3) 0.81202(11) 0.0278(7) Uani 1 1 d . . . H17 H 0.1301 0.8730 0.8343 0.033 Uiso 1 1 calc R . . C18 C 0.1487(3) 0.9644(3) 0.77248(10) 0.0260(6) Uani 1 1 d . . . H18 H 0.2387 0.9432 0.7682 0.031 Uiso 1 1 calc R . . C19 C 0.1542(3) 1.0830(3) 0.69565(9) 0.0216(6) Uani 1 1 d . . . H19 H 0.0899 1.1284 0.6756 0.026 Uiso 1 1 calc R . . C20 C 0.2198(3) 0.9646(3) 0.66869(9) 0.0207(6) Uani 1 1 d . . . H20 H 0.1997 0.8827 0.6857 0.025 Uiso 1 1 calc R . . C21 C 0.2723(3) 1.1771(3) 0.70543(10) 0.0251(7) Uani 1 1 d . . . H21A H 0.2886 1.2369 0.6798 0.030 Uiso 1 1 calc R . . H21B H 0.2572 1.2292 0.7330 0.030 Uiso 1 1 calc R . . C22 C 0.3727(3) 0.9884(3) 0.67232(10) 0.0236(6) Uani 1 1 d . . . H22A H 0.4202 0.9058 0.6784 0.028 Uiso 1 1 calc R . . H22B H 0.4078 1.0280 0.6444 0.028 Uiso 1 1 calc R . . C23 C 0.5796(3) 1.2384(3) 0.67695(10) 0.0222(6) Uani 1 1 d . . . C24 C 0.5376(3) 1.3714(3) 0.67557(10) 0.0253(6) Uani 1 1 d . . . H24 H 0.4936 1.4093 0.7005 0.030 Uiso 1 1 calc R . . C25 C 0.5625(3) 1.4453(3) 0.63662(10) 0.0275(7) Uani 1 1 d . . . H25 H 0.5357 1.5341 0.6358 0.033 Uiso 1 1 calc R . . C26 C 0.6264(3) 1.3911(3) 0.59858(10) 0.0277(7) Uani 1 1 d . . . C27 C 0.6519(4) 1.4737(3) 0.55623(11) 0.0384(8) Uani 1 1 d . . . H27A H 0.6968 1.4203 0.5336 0.058 Uiso 1 1 calc R . . H27B H 0.7070 1.5489 0.5641 0.058 Uiso 1 1 calc R . . H27C H 0.5680 1.5046 0.5440 0.058 Uiso 1 1 calc R . . C28 C 0.6666(3) 1.2580(3) 0.60072(10) 0.0277(7) Uani 1 1 d . . . H28 H 0.7090 1.2196 0.5755 0.033 Uiso 1 1 calc R . . C29 C 0.6445(3) 1.1823(3) 0.63947(10) 0.0259(7) Uani 1 1 d . . . H29 H 0.6730 1.0940 0.6405 0.031 Uiso 1 1 calc R . . C30 C 0.2621(3) 0.6871(3) 0.61090(11) 0.0331(7) Uani 1 1 d . . . H30A H 0.1771 0.6610 0.6235 0.050 Uiso 1 1 calc R . . H30B H 0.3205 0.7150 0.6353 0.050 Uiso 1 1 calc R . . H30C H 0.3016 0.6127 0.5951 0.050 Uiso 1 1 calc R . . C31 C 0.1563(3) 0.7516(3) 0.53695(10) 0.0322(7) Uani 1 1 d . . . H31A H 0.0700 0.7245 0.5482 0.048 Uiso 1 1 calc R . . H31B H 0.2003 0.6767 0.5229 0.048 Uiso 1 1 calc R . . H31C H 0.1451 0.8211 0.5146 0.048 Uiso 1 1 calc R . . C32 C 0.3785(3) 0.8442(3) 0.55712(11) 0.0330(8) Uani 1 1 d . . . H32A H 0.4347 0.8772 0.5814 0.049 Uiso 1 1 calc R . . H32B H 0.3660 0.9127 0.5345 0.049 Uiso 1 1 calc R . . H32C H 0.4203 0.7681 0.5431 0.049 Uiso 1 1 calc R . . C33 C 0.2417(3) 0.8034(3) 0.57697(10) 0.0246(7) Uani 1 1 d . . . N1 N 0.3840(2) 1.0817(2) 0.71151(8) 0.0218(5) Uani 1 1 d . . . O1 O 0.62035(19) 1.02470(19) 0.72490(7) 0.0303(5) Uani 1 1 d . . . O2 O 0.5200(2) 1.2201(2) 0.76365(7) 0.0307(5) Uani 1 1 d . . . F1 F -0.11372(17) 0.90934(17) 0.85543(6) 0.0333(4) Uani 1 1 d . . . Si1 Si 0.15022(8) 0.94276(8) 0.60874(3) 0.02078(19) Uani 1 1 d . . . S1 S 0.53350(7) 1.13823(7) 0.72393(3) 0.02429(18) 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 0.0257(15) 0.0242(14) 0.0179(14) -0.0023(12) -0.0001(13) -0.0010(13) C2 0.0280(16) 0.0301(16) 0.0269(16) 0.0006(14) -0.0011(13) -0.0023(13) C3 0.0407(19) 0.0310(17) 0.0363(19) -0.0009(16) 0.0020(16) -0.0110(15) C4 0.056(2) 0.0228(15) 0.0328(18) 0.0031(15) -0.0056(17) -0.0049(16) C5 0.042(2) 0.0262(16) 0.0406(19) 0.0018(16) -0.0091(17) 0.0072(15) C6 0.0245(16) 0.0287(16) 0.0345(17) -0.0016(15) -0.0049(14) 0.0038(13) C7 0.0202(14) 0.0235(15) 0.0231(15) -0.0040(13) -0.0018(13) 0.0000(12) C8 0.0245(16) 0.0309(16) 0.0225(15) 0.0016(13) 0.0030(13) -0.0030(13) C9 0.0209(15) 0.0324(16) 0.0279(16) -0.0041(15) -0.0064(13) -0.0020(14) C10 0.0181(14) 0.0297(16) 0.0329(17) -0.0058(14) 0.0028(13) -0.0047(13) C11 0.0287(17) 0.0324(16) 0.0299(17) 0.0037(15) 0.0054(14) -0.0042(14) C12 0.0250(15) 0.0266(16) 0.0270(16) -0.0034(14) -0.0024(13) -0.0014(12) C13 0.0208(14) 0.0233(14) 0.0204(15) -0.0027(13) -0.0004(12) 0.0017(12) C14 0.0205(14) 0.0315(16) 0.0226(15) 0.0030(14) -0.0045(13) 0.0022(13) C15 0.0171(14) 0.0370(17) 0.0261(17) -0.0034(14) 0.0016(12) -0.0005(12) C16 0.0281(16) 0.0260(14) 0.0192(15) -0.0017(13) 0.0023(13) -0.0043(13) C17 0.0296(16) 0.0287(15) 0.0249(16) 0.0034(14) -0.0052(13) 0.0008(13) C18 0.0209(14) 0.0324(15) 0.0246(15) 0.0032(14) -0.0005(13) 0.0042(13) C19 0.0205(14) 0.0239(14) 0.0205(15) -0.0003(12) -0.0059(12) 0.0024(12) C20 0.0213(14) 0.0210(14) 0.0199(14) 0.0009(13) -0.0013(12) -0.0037(12) C21 0.0233(15) 0.0250(15) 0.0268(16) 0.0019(13) 0.0036(13) 0.0011(12) C22 0.0190(15) 0.0284(15) 0.0234(15) -0.0021(13) -0.0044(13) 0.0007(12) C23 0.0190(14) 0.0232(14) 0.0245(16) -0.0024(13) -0.0048(12) -0.0038(11) C24 0.0217(14) 0.0244(14) 0.0297(16) -0.0056(14) -0.0012(13) 0.0007(13) C25 0.0258(16) 0.0245(15) 0.0321(17) 0.0001(15) -0.0027(13) -0.0004(13) C26 0.0231(15) 0.0316(16) 0.0283(17) 0.0012(14) -0.0035(13) -0.0050(13) C27 0.0405(19) 0.0387(18) 0.0359(19) 0.0081(16) 0.0038(17) 0.0001(17) C28 0.0229(15) 0.0328(16) 0.0275(17) -0.0036(14) 0.0013(14) -0.0005(13) C29 0.0196(14) 0.0238(14) 0.0344(17) -0.0001(13) -0.0041(14) -0.0012(12) C30 0.0353(18) 0.0273(16) 0.0368(18) -0.0011(15) 0.0003(16) 0.0076(14) C31 0.0383(18) 0.0294(16) 0.0288(17) -0.0068(14) -0.0009(15) 0.0023(15) C32 0.0256(16) 0.0386(17) 0.0347(18) -0.0084(16) 0.0067(14) 0.0041(14) C33 0.0254(16) 0.0271(15) 0.0214(15) -0.0016(13) -0.0006(13) 0.0021(13) N1 0.0183(12) 0.0214(12) 0.0258(13) -0.0012(11) -0.0029(10) -0.0005(10) O1 0.0234(11) 0.0318(11) 0.0357(12) 0.0068(10) -0.0078(10) 0.0010(9) O2 0.0311(11) 0.0372(12) 0.0239(11) -0.0003(10) -0.0039(9) -0.0083(10) F1 0.0346(10) 0.0394(10) 0.0259(9) 0.0041(8) 0.0062(8) -0.0029(8) Si1 0.0176(4) 0.0240(4) 0.0207(4) 0.0010(4) -0.0013(3) 0.0002(3) S1 0.0222(4) 0.0270(4) 0.0237(4) 0.0009(3) -0.0048(3) -0.0035(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 1.409(4) . ? C1 C6 1.412(4) . ? C1 Si1 1.885(3) . ? C2 C3 1.386(4) . ? C2 H2 0.9300 . ? C3 C4 1.381(5) . ? C3 H3 0.9300 . ? C4 C5 1.381(5) . ? C4 H4 0.9300 . ? C5 C6 1.369(4) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? C7 C12 1.399(4) . ? C7 C8 1.405(4) . ? C7 Si1 1.881(3) . ? C8 C9 1.387(4) . ? C8 H8 0.9300 . ? C9 C10 1.379(4) . ? C9 H9 0.9300 . ? C10 C11 1.372(4) . ? C10 H10 0.9300 . ? C11 C12 1.384(4) . ? C11 H11 0.9300 . ? C12 H12 0.9300 . ? C13 C18 1.391(4) . ? C13 C14 1.393(4) . ? C13 C19 1.516(4) . ? C14 C15 1.383(4) . ? C14 H14 0.9300 . ? C15 C16 1.367(4) . ? C15 H15 0.9300 . ? C16 F1 1.363(3) . ? C16 C17 1.377(4) . ? C17 C18 1.385(4) . ? C17 H17 0.9300 . ? C18 H18 0.9300 . ? C19 C21 1.536(4) . ? C19 C20 1.566(4) . ? C19 H19 0.9800 . ? C20 C22 1.547(4) . ? C20 Si1 1.890(3) . ? C20 H20 0.9800 . ? C21 N1 1.478(3) . ? C21 H21A 0.9700 . ? C21 H21B 0.9700 . ? C22 N1 1.479(3) . ? C22 H22A 0.9700 . ? C22 H22B 0.9700 . ? C23 C29 1.387(4) . ? C23 C24 1.398(4) . ? C23 S1 1.757(3) . ? C24 C25 1.377(4) . ? C24 H24 0.9300 . ? C25 C26 1.388(4) . ? C25 H25 0.9300 . ? C26 C28 1.394(4) . ? C26 C27 1.507(4) . ? C27 H27A 0.9600 . ? C27 H27B 0.9600 . ? C27 H27C 0.9600 . ? C28 C29 1.377(4) . ? C28 H28 0.9300 . ? C29 H29 0.9300 . ? C30 C33 1.542(4) . ? C30 H30A 0.9600 . ? C30 H30B 0.9600 . ? C30 H30C 0.9600 . ? C31 C33 1.534(4) . ? C31 H31A 0.9600 . ? C31 H31B 0.9600 . ? C31 H31C 0.9600 . ? C32 C33 1.537(4) . ? C32 H32A 0.9600 . ? C32 H32B 0.9600 . ? C32 H32C 0.9600 . ? C33 Si1 1.908(3) . ? N1 S1 1.635(2) . ? O1 S1 1.430(2) . ? O2 S1 1.424(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 C2 C1 C6 115.1(3) . . ? C2 C1 Si1 122.7(2) . . ? C6 C1 Si1 122.1(2) . . ? C3 C2 C1 122.3(3) . . ? C3 C2 H2 118.8 . . ? C1 C2 H2 118.8 . . ? C4 C3 C2 120.0(3) . . ? C4 C3 H3 120.0 . . ? C2 C3 H3 120.0 . . ? C5 C4 C3 119.6(3) . . ? C5 C4 H4 120.2 . . ? C3 C4 H4 120.2 . . ? C6 C5 C4 120.2(3) . . ? C6 C5 H5 119.9 . . ? C4 C5 H5 119.9 . . ? C5 C6 C1 122.8(3) . . ? C5 C6 H6 118.6 . . ? C1 C6 H6 118.6 . . ? C12 C7 C8 116.3(3) . . ? C12 C7 Si1 121.5(2) . . ? C8 C7 Si1 122.1(2) . . ? C9 C8 C7 121.8(3) . . ? C9 C8 H8 119.1 . . ? C7 C8 H8 119.1 . . ? C10 C9 C8 120.0(3) . . ? C10 C9 H9 120.0 . . ? C8 C9 H9 120.0 . . ? C11 C10 C9 119.6(3) . . ? C11 C10 H10 120.2 . . ? C9 C10 H10 120.2 . . ? C10 C11 C12 120.6(3) . . ? C10 C11 H11 119.7 . . ? C12 C11 H11 119.7 . . ? C11 C12 C7 121.6(3) . . ? C11 C12 H12 119.2 . . ? C7 C12 H12 119.2 . . ? C18 C13 C14 117.9(3) . . ? C18 C13 C19 121.2(2) . . ? C14 C13 C19 120.9(3) . . ? C15 C14 C13 121.0(3) . . ? C15 C14 H14 119.5 . . ? C13 C14 H14 119.5 . . ? C16 C15 C14 118.8(3) . . ? C16 C15 H15 120.6 . . ? C14 C15 H15 120.6 . . ? F1 C16 C15 119.2(3) . . ? F1 C16 C17 118.1(3) . . ? C15 C16 C17 122.6(3) . . ? C16 C17 C18 117.6(3) . . ? C16 C17 H17 121.2 . . ? C18 C17 H17 121.2 . . ? C17 C18 C13 122.0(3) . . ? C17 C18 H18 119.0 . . ? C13 C18 H18 119.0 . . ? C13 C19 C21 112.9(2) . . ? C13 C19 C20 112.9(2) . . ? C21 C19 C20 103.8(2) . . ? C13 C19 H19 109.1 . . ? C21 C19 H19 109.1 . . ? C20 C19 H19 109.1 . . ? C22 C20 C19 105.1(2) . . ? C22 C20 Si1 116.26(19) . . ? C19 C20 Si1 113.39(19) . . ? C22 C20 H20 107.2 . . ? C19 C20 H20 107.2 . . ? Si1 C20 H20 107.2 . . ? N1 C21 C19 101.7(2) . . ? N1 C21 H21A 111.4 . . ? C19 C21 H21A 111.4 . . ? N1 C21 H21B 111.4 . . ? C19 C21 H21B 111.4 . . ? H21A C21 H21B 109.3 . . ? N1 C22 C20 103.0(2) . . ? N1 C22 H22A 111.2 . . ? C20 C22 H22A 111.2 . . ? N1 C22 H22B 111.2 . . ? C20 C22 H22B 111.2 . . ? H22A C22 H22B 109.1 . . ? C29 C23 C24 120.2(3) . . ? C29 C23 S1 120.2(2) . . ? C24 C23 S1 119.3(2) . . ? C25 C24 C23 118.9(3) . . ? C25 C24 H24 120.6 . . ? C23 C24 H24 120.6 . . ? C24 C25 C26 121.9(3) . . ? C24 C25 H25 119.0 . . ? C26 C25 H25 119.0 . . ? C25 C26 C28 118.1(3) . . ? C25 C26 C27 121.0(3) . . ? C28 C26 C27 121.0(3) . . ? C26 C27 H27A 109.5 . . ? C26 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? C26 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? C29 C28 C26 121.2(3) . . ? C29 C28 H28 119.4 . . ? C26 C28 H28 119.4 . . ? C28 C29 C23 119.7(3) . . ? C28 C29 H29 120.2 . . ? C23 C29 H29 120.2 . . ? C33 C30 H30A 109.5 . . ? C33 C30 H30B 109.5 . . ? H30A C30 H30B 109.5 . . ? C33 C30 H30C 109.5 . . ? H30A C30 H30C 109.5 . . ? H30B C30 H30C 109.5 . . ? C33 C31 H31A 109.5 . . ? C33 C31 H31B 109.5 . . ? H31A C31 H31B 109.5 . . ? C33 C31 H31C 109.5 . . ? H31A C31 H31C 109.5 . . ? H31B C31 H31C 109.5 . . ? C33 C32 H32A 109.5 . . ? C33 C32 H32B 109.5 . . ? H32A C32 H32B 109.5 . . ? C33 C32 H32C 109.5 . . ? H32A C32 H32C 109.5 . . ? H32B C32 H32C 109.5 . . ? C31 C33 C32 107.3(2) . . ? C31 C33 C30 107.7(2) . . ? C32 C33 C30 109.0(2) . . ? C31 C33 Si1 110.5(2) . . ? C32 C33 Si1 114.3(2) . . ? C30 C33 Si1 107.85(19) . . ? C21 N1 C22 105.1(2) . . ? C21 N1 S1 119.25(18) . . ? C22 N1 S1 117.29(18) . . ? C7 Si1 C1 110.03(13) . . ? C7 Si1 C20 106.87(13) . . ? C1 Si1 C20 108.92(12) . . ? C7 Si1 C33 107.43(13) . . ? C1 Si1 C33 112.53(13) . . ? C20 Si1 C33 110.90(13) . . ? O2 S1 O1 119.97(13) . . ? O2 S1 N1 107.05(12) . . ? O1 S1 N1 106.28(12) . . ? O2 S1 C23 109.11(13) . . ? O1 S1 C23 108.15(13) . . ? N1 S1 C23 105.33(13) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 -2.5(4) . . . . ? Si1 C1 C2 C3 -179.8(2) . . . . ? C1 C2 C3 C4 0.4(5) . . . . ? C2 C3 C4 C5 1.2(5) . . . . ? C3 C4 C5 C6 -0.6(5) . . . . ? C4 C5 C6 C1 -1.7(5) . . . . ? C2 C1 C6 C5 3.1(4) . . . . ? Si1 C1 C6 C5 -179.5(2) . . . . ? C12 C7 C8 C9 1.5(4) . . . . ? Si1 C7 C8 C9 178.5(2) . . . . ? C7 C8 C9 C10 -0.9(4) . . . . ? C8 C9 C10 C11 -0.1(5) . . . . ? C9 C10 C11 C12 0.5(5) . . . . ? C10 C11 C12 C7 0.1(5) . . . . ? C8 C7 C12 C11 -1.1(4) . . . . ? Si1 C7 C12 C11 -178.2(2) . . . . ? C18 C13 C14 C15 0.0(4) . . . . ? C19 C13 C14 C15 179.0(3) . . . . ? C13 C14 C15 C16 0.0(4) . . . . ? C14 C15 C16 F1 -178.9(2) . . . . ? C14 C15 C16 C17 0.3(4) . . . . ? F1 C16 C17 C18 178.6(2) . . . . ? C15 C16 C17 C18 -0.6(4) . . . . ? C16 C17 C18 C13 0.6(4) . . . . ? C14 C13 C18 C17 -0.3(4) . . . . ? C19 C13 C18 C17 -179.4(3) . . . . ? C18 C13 C19 C21 -62.2(3) . . . . ? C14 C13 C19 C21 118.8(3) . . . . ? C18 C13 C19 C20 55.1(3) . . . . ? C14 C13 C19 C20 -123.9(3) . . . . ? C13 C19 C20 C22 -113.3(2) . . . . ? C21 C19 C20 C22 9.3(3) . . . . ? C13 C19 C20 Si1 118.7(2) . . . . ? C21 C19 C20 Si1 -118.7(2) . . . . ? C13 C19 C21 N1 89.0(3) . . . . ? C20 C19 C21 N1 -33.5(3) . . . . ? C19 C20 C22 N1 18.4(3) . . . . ? Si1 C20 C22 N1 144.70(19) . . . . ? C29 C23 C24 C25 -0.3(4) . . . . ? S1 C23 C24 C25 -173.5(2) . . . . ? C23 C24 C25 C26 0.8(4) . . . . ? C24 C25 C26 C28 -0.4(4) . . . . ? C24 C25 C26 C27 179.7(3) . . . . ? C25 C26 C28 C29 -0.4(4) . . . . ? C27 C26 C28 C29 179.5(3) . . . . ? C26 C28 C29 C23 0.9(4) . . . . ? C24 C23 C29 C28 -0.5(4) . . . . ? S1 C23 C29 C28 172.6(2) . . . . ? C19 C21 N1 C22 47.3(3) . . . . ? C19 C21 N1 S1 -178.72(18) . . . . ? C20 C22 N1 C21 -41.1(3) . . . . ? C20 C22 N1 S1 -176.21(18) . . . . ? C12 C7 Si1 C1 -139.1(2) . . . . ? C8 C7 Si1 C1 44.0(3) . . . . ? C12 C7 Si1 C20 -21.0(3) . . . . ? C8 C7 Si1 C20 162.1(2) . . . . ? C12 C7 Si1 C33 98.1(2) . . . . ? C8 C7 Si1 C33 -78.8(3) . . . . ? C2 C1 Si1 C7 -173.8(2) . . . . ? C6 C1 Si1 C7 9.1(3) . . . . ? C2 C1 Si1 C20 69.4(3) . . . . ? C6 C1 Si1 C20 -107.7(2) . . . . ? C2 C1 Si1 C33 -54.0(3) . . . . ? C6 C1 Si1 C33 128.9(2) . . . . ? C22 C20 Si1 C7 171.6(2) . . . . ? C19 C20 Si1 C7 -66.4(2) . . . . ? C22 C20 Si1 C1 -69.6(2) . . . . ? C19 C20 Si1 C1 52.4(2) . . . . ? C22 C20 Si1 C33 54.8(2) . . . . ? C19 C20 Si1 C33 176.79(19) . . . . ? C31 C33 Si1 C7 42.9(2) . . . . ? C32 C33 Si1 C7 164.1(2) . . . . ? C30 C33 Si1 C7 -74.5(2) . . . . ? C31 C33 Si1 C1 -78.3(2) . . . . ? C32 C33 Si1 C1 42.8(2) . . . . ? C30 C33 Si1 C1 164.20(19) . . . . ? C31 C33 Si1 C20 159.4(2) . . . . ? C32 C33 Si1 C20 -79.4(2) . . . . ? C30 C33 Si1 C20 41.9(2) . . . . ? C21 N1 S1 O2 54.0(2) . . . . ? C22 N1 S1 O2 -177.36(19) . . . . ? C21 N1 S1 O1 -176.6(2) . . . . ? C22 N1 S1 O1 -48.0(2) . . . . ? C21 N1 S1 C23 -62.0(2) . . . . ? C22 N1 S1 C23 66.6(2) . . . . ? C29 C23 S1 O2 156.9(2) . . . . ? C24 C23 S1 O2 -29.9(3) . . . . ? C29 C23 S1 O1 24.8(3) . . . . ? C24 C23 S1 O1 -162.0(2) . . . . ? C29 C23 S1 N1 -88.5(2) . . . . ? C24 C23 S1 N1 84.7(2) . . . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.382 _refine_diff_density_min -0.295 _refine_diff_density_rms 0.061 # Attachment '5a R = benzyl.cif' data_1auge _database_code_depnum_ccdc_archive 'CCDC 859596' #TrackingRef '5a R = benzyl.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common sulfoxide _chemical_melting_point ? _chemical_formula_moiety 'C35 H41 N O3 S Si' _chemical_formula_sum 'C35 H41 N O3 S Si' _chemical_formula_weight 583.84 _chemical_absolute_configuration syn 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 'P 2(1)' _symmetry_space_group_name_HALL 'P 2yb' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 13.4861(14) _cell_length_b 8.3629(9) _cell_length_c 14.9897(16) _cell_angle_alpha 90.00 _cell_angle_beta 110.252(2) _cell_angle_gamma 90.00 _cell_volume 1586.1(3) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 2186 _cell_measurement_theta_min 2.51 _cell_measurement_theta_max 24.08 _exptl_crystal_description block _exptl_crystal_colour colorless _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 1.223 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 624 _exptl_absorpt_coefficient_mu 0.175 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9659 _exptl_absorpt_correction_T_max 0.9659 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8529 _diffrn_reflns_av_R_equivalents 0.0407 _diffrn_reflns_av_sigmaI/netI 0.0662 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.51 _diffrn_reflns_theta_max 25.50 _reflns_number_total 4967 _reflns_number_gt 4340 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART 5.628 (Bruker, 2003)' _computing_cell_refinement 'SMART 5.628 (Bruker, 2003)' _computing_data_reduction 'SAINT+ 6.45 (Bruker, 2003)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'diamond 3.1d' _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^)+(0.0542P)^2^+0.0315P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.03(9) _refine_ls_number_reflns 4967 _refine_ls_number_parameters 379 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0549 _refine_ls_R_factor_gt 0.0462 _refine_ls_wR_factor_ref 0.1103 _refine_ls_wR_factor_gt 0.1030 _refine_ls_goodness_of_fit_ref 1.026 _refine_ls_restrained_S_all 1.025 _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 S01 S 0.54891(6) 0.78372(10) 0.44902(5) 0.0217(2) Uani 1 1 d . . . Si2 Si 0.69550(6) 0.75514(12) 0.81022(6) 0.0191(2) Uani 1 1 d . . . O3 O 0.50237(18) 0.8849(3) 0.50719(16) 0.0267(5) Uani 1 1 d . . . O4 O 0.89803(16) 0.7682(3) 0.57069(14) 0.0269(5) Uani 1 1 d . . . O5 O 0.85743(17) 0.5257(3) 0.50427(15) 0.0281(6) Uani 1 1 d . . . N6 N 0.6332(2) 0.6521(3) 0.51519(18) 0.0197(6) Uani 1 1 d . . . C7 C 0.5518(2) 0.5220(4) 0.8381(2) 0.0229(7) Uani 1 1 d . . . H7 H 0.5233 0.5184 0.7706 0.028 Uiso 1 1 calc R . . C8 C 0.8057(2) 0.5963(4) 0.6386(2) 0.0194(7) Uani 1 1 d . . . H8 H 0.8558 0.6412 0.6993 0.023 Uiso 1 1 calc R . . C9 C 0.6442(2) 0.6750(4) 0.6841(2) 0.0209(7) Uani 1 1 d . . . H9A H 0.6343 0.5585 0.6892 0.025 Uiso 1 1 calc R . . H9B H 0.5727 0.7211 0.6536 0.025 Uiso 1 1 calc R . . C10 C 0.6722(3) 0.6268(5) 0.9821(2) 0.0284(8) Uani 1 1 d . . . H10 H 0.7284 0.6966 1.0153 0.034 Uiso 1 1 calc R . . C11 C 0.7942(3) 0.4188(4) 0.6555(2) 0.0245(8) Uani 1 1 d . . . H1A H 0.7552 0.4056 0.7001 0.029 Uiso 1 1 calc R . . H1B H 0.7523 0.3673 0.5946 0.029 Uiso 1 1 calc R . . C12 C 0.7025(2) 0.6967(4) 0.6126(2) 0.0183(7) Uani 1 1 d . . . H12 H 0.7216 0.8122 0.6121 0.022 Uiso 1 1 calc R . . C13 C 0.6938(3) 1.1821(5) 0.4018(2) 0.0296(8) Uani 1 1 d . . . H13 H 0.6975 1.2921 0.4184 0.036 Uiso 1 1 calc R . . C14 C 0.5472(3) 0.4286(5) 0.9880(2) 0.0294(8) Uani 1 1 d . . . H14 H 0.5183 0.3608 1.0236 0.035 Uiso 1 1 calc R . . C15 C 0.5221(2) 0.9651(4) 0.7728(2) 0.0277(8) Uani 1 1 d . . . H1C H 0.4974 0.9345 0.7055 0.042 Uiso 1 1 calc R . . H1D H 0.4951 1.0716 0.7793 0.042 Uiso 1 1 calc R . . H1E H 0.4964 0.8875 0.8087 0.042 Uiso 1 1 calc R . . C16 C 0.7416(3) 1.1302(5) 0.3395(2) 0.0294(8) Uani 1 1 d . . . C17 C 0.9513(3) 0.8043(5) 0.5038(2) 0.0382(10) Uani 1 1 d . . . H1F H 0.9031 0.7842 0.4389 0.057 Uiso 1 1 calc R . . H1G H 1.0139 0.7362 0.5173 0.057 Uiso 1 1 calc R . . H1H H 0.9728 0.9169 0.5102 0.057 Uiso 1 1 calc R . . C18 C 0.6286(3) 0.5314(5) 1.0335(2) 0.0297(8) Uani 1 1 d . . . H18 H 0.6550 0.5365 1.1010 0.036 Uiso 1 1 calc R . . C19 C 0.6359(2) 0.9169(4) 0.4173(2) 0.0223(7) Uani 1 1 d . . . C20 C 0.6814(3) 1.0300(5) 0.9150(2) 0.0305(8) Uani 1 1 d . . . H2A H 0.6518 0.9629 0.9533 0.046 Uiso 1 1 calc R . . H2B H 0.6575 1.1405 0.9156 0.046 Uiso 1 1 calc R . . H2C H 0.7588 1.0263 0.9418 0.046 Uiso 1 1 calc R . . C21 C 0.8988(3) 0.6551(5) 0.9433(2) 0.0299(8) Uani 1 1 d . . . H21 H 0.8598 0.5892 0.9709 0.036 Uiso 1 1 calc R . . C22 C 0.9004(3) 0.3363(4) 0.6959(2) 0.0245(8) Uani 1 1 d . . . C23 C 0.6368(2) 0.6251(4) 0.8820(2) 0.0210(7) Uani 1 1 d . . . C24 C 0.8555(2) 0.6223(4) 0.5632(2) 0.0212(7) Uani 1 1 d . . . C25 C 0.8448(2) 0.7501(4) 0.86503(19) 0.0193(7) Uani 1 1 d . . . C26 C 0.6439(2) 0.9676(4) 0.8119(2) 0.0227(7) Uani 1 1 d . . . C27 C 1.0671(2) 0.7488(5) 0.9430(2) 0.0289(8) Uani 1 1 d . . . H27 H 1.1421 0.7489 0.9701 0.035 Uiso 1 1 calc R . . C28 C 1.0980(3) 0.1894(5) 0.7718(3) 0.0327(9) Uani 1 1 d . . . H28 H 1.1657 0.1406 0.7966 0.039 Uiso 1 1 calc R . . C29 C 0.5081(3) 0.4253(5) 0.8897(2) 0.0307(8) Uani 1 1 d . . . H29 H 0.4509 0.3565 0.8575 0.037 Uiso 1 1 calc R . . C30 C 0.6403(2) 1.0778(4) 0.4406(2) 0.0244(8) Uani 1 1 d . . . H30 H 0.6069 1.1160 0.4828 0.029 Uiso 1 1 calc R . . C31 C 0.9786(3) 0.3962(5) 0.7765(2) 0.0335(9) Uani 1 1 d . . . H31 H 0.9645 0.4892 0.8065 0.040 Uiso 1 1 calc R . . C32 C 0.9072(3) 0.8435(4) 0.8270(2) 0.0224(7) Uani 1 1 d . . . H32 H 0.8732 0.9096 0.7736 0.027 Uiso 1 1 calc R . . C33 C 1.0762(3) 0.3233(5) 0.8138(3) 0.0365(9) Uani 1 1 d . . . H33 H 1.1283 0.3664 0.8688 0.044 Uiso 1 1 calc R . . C34 C 1.0091(3) 0.6554(5) 0.9817(2) 0.0343(9) Uani 1 1 d . . . H34 H 1.0442 0.5901 1.0352 0.041 Uiso 1 1 calc R . . C35 C 0.6860(3) 0.8601(4) 0.3563(2) 0.0275(8) Uani 1 1 d . . . H35 H 0.6843 0.7496 0.3412 0.033 Uiso 1 1 calc R . . C36 C 1.0170(3) 0.8423(4) 0.8650(2) 0.0278(8) Uani 1 1 d . . . H36 H 1.0571 0.9056 0.8372 0.033 Uiso 1 1 calc R . . C37 C 0.7937(3) 1.2467(6) 0.2926(3) 0.0441(10) Uani 1 1 d . . . H3A H 0.7482 1.2631 0.2263 0.066 Uiso 1 1 calc R . . H3B H 0.8620 1.2037 0.2945 0.066 Uiso 1 1 calc R . . H3C H 0.8047 1.3490 0.3265 0.066 Uiso 1 1 calc R . . C38 C 0.9235(3) 0.1984(4) 0.6561(2) 0.0266(8) Uani 1 1 d . . . H38 H 0.8710 0.1531 0.6021 0.032 Uiso 1 1 calc R . . C39 C 0.7384(3) 0.9679(5) 0.3183(2) 0.0336(9) Uani 1 1 d . . . H39 H 0.7729 0.9302 0.2769 0.040 Uiso 1 1 calc R . . C40 C 1.0209(3) 0.1250(5) 0.6929(2) 0.0345(9) Uani 1 1 d . . . H40 H 1.0351 0.0306 0.6641 0.041 Uiso 1 1 calc R . . C41 C 0.6822(3) 1.0840(5) 0.7511(3) 0.0317(8) Uani 1 1 d . . . H4A H 0.6500 1.1892 0.7505 0.048 Uiso 1 1 calc R . . H4B H 0.6618 1.0431 0.6859 0.048 Uiso 1 1 calc R . . H4C H 0.7593 1.0937 0.7781 0.048 Uiso 1 1 calc R . . H19 H 0.601(3) 0.565(5) 0.520(2) 0.035(11) 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 S01 0.0183(4) 0.0247(5) 0.0211(4) 0.0032(4) 0.0056(3) 0.0002(3) Si2 0.0166(4) 0.0218(5) 0.0187(4) -0.0003(4) 0.0060(3) -0.0007(4) O3 0.0284(12) 0.0256(14) 0.0308(12) 0.0073(11) 0.0164(10) 0.0072(10) O4 0.0317(12) 0.0263(14) 0.0278(11) -0.0025(12) 0.0169(10) -0.0095(12) O5 0.0306(13) 0.0264(14) 0.0288(12) -0.0052(12) 0.0123(10) 0.0044(11) N6 0.0219(14) 0.0154(16) 0.0217(14) -0.0005(12) 0.0075(11) -0.0001(12) C7 0.0247(17) 0.024(2) 0.0198(16) 0.0000(15) 0.0071(14) -0.0038(15) C8 0.0186(16) 0.0191(18) 0.0207(16) -0.0004(14) 0.0070(13) 0.0013(13) C9 0.0194(17) 0.0186(18) 0.0254(17) 0.0007(14) 0.0084(13) 0.0016(13) C10 0.0248(18) 0.038(2) 0.0220(17) -0.0018(16) 0.0071(14) -0.0047(16) C11 0.0261(18) 0.0206(19) 0.0284(18) 0.0032(15) 0.0113(14) -0.0002(14) C12 0.0184(16) 0.0179(17) 0.0179(15) 0.0005(13) 0.0056(13) -0.0003(13) C13 0.0264(19) 0.025(2) 0.0296(19) 0.0078(16) 0.0002(15) -0.0013(15) C14 0.0300(19) 0.031(2) 0.034(2) 0.0066(17) 0.0190(16) 0.0007(16) C15 0.0285(18) 0.025(2) 0.0293(18) -0.0021(16) 0.0102(15) 0.0039(15) C16 0.0209(18) 0.036(2) 0.0284(18) 0.0090(17) 0.0052(15) 0.0009(16) C17 0.039(2) 0.049(3) 0.0351(19) 0.001(2) 0.0225(17) -0.0146(19) C18 0.0317(19) 0.038(2) 0.0214(17) 0.0031(17) 0.0112(15) -0.0010(17) C19 0.0185(16) 0.0238(19) 0.0213(17) 0.0059(15) 0.0027(13) 0.0005(14) C20 0.0262(18) 0.029(2) 0.035(2) -0.0074(17) 0.0090(16) 0.0002(16) C21 0.0295(19) 0.032(2) 0.0297(18) 0.0103(16) 0.0120(16) 0.0032(16) C22 0.0280(18) 0.023(2) 0.0248(17) 0.0047(15) 0.0118(15) 0.0008(14) C23 0.0175(16) 0.025(2) 0.0205(16) 0.0017(15) 0.0068(13) 0.0043(14) C24 0.0181(16) 0.0225(19) 0.0195(16) 0.0032(15) 0.0019(13) 0.0016(14) C25 0.0203(15) 0.0202(18) 0.0192(14) -0.0021(15) 0.0092(12) -0.0013(14) C26 0.0202(16) 0.0228(19) 0.0265(17) -0.0012(15) 0.0098(14) 0.0017(14) C27 0.0156(15) 0.033(2) 0.0360(18) -0.0029(18) 0.0060(14) -0.0001(16) C28 0.0261(19) 0.032(2) 0.039(2) 0.0135(18) 0.0092(17) 0.0072(16) C29 0.0312(19) 0.030(2) 0.0330(19) -0.0041(17) 0.0143(16) -0.0072(16) C30 0.0221(17) 0.027(2) 0.0221(17) -0.0006(15) 0.0054(14) 0.0004(15) C31 0.036(2) 0.024(2) 0.035(2) -0.0047(17) 0.0055(16) 0.0109(16) C32 0.0241(17) 0.0186(18) 0.0243(16) -0.0014(14) 0.0083(14) 0.0009(13) C33 0.036(2) 0.028(2) 0.035(2) 0.0029(18) -0.0005(16) -0.0001(17) C34 0.0263(19) 0.042(2) 0.0290(19) 0.0102(18) 0.0022(15) 0.0074(17) C35 0.035(2) 0.022(2) 0.0279(18) 0.0013(16) 0.0142(16) 0.0047(15) C36 0.0259(18) 0.023(2) 0.0351(19) 0.0016(16) 0.0109(15) -0.0050(14) C37 0.042(2) 0.046(3) 0.044(2) 0.014(2) 0.0138(17) -0.010(2) C38 0.0299(19) 0.024(2) 0.0226(17) 0.0010(15) 0.0048(15) 0.0041(15) C39 0.033(2) 0.043(3) 0.0304(19) 0.0064(18) 0.0179(16) 0.0049(18) C40 0.047(2) 0.025(2) 0.035(2) 0.0031(18) 0.0198(18) 0.0153(18) C41 0.035(2) 0.023(2) 0.039(2) 0.0050(17) 0.0150(16) 0.0065(16) _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 S01 O3 1.500(2) . ? S01 N6 1.646(3) . ? S01 C19 1.798(3) . ? Si2 C23 1.886(3) . ? Si2 C25 1.894(3) . ? Si2 C9 1.897(3) . ? Si2 C26 1.911(4) . ? O4 C24 1.336(4) . ? O4 C17 1.453(4) . ? O5 C24 1.205(4) . ? N6 C12 1.483(4) . ? N6 H19 0.87(4) . ? C7 C29 1.384(5) . ? C7 C23 1.403(4) . ? C7 H7 0.9500 . ? C8 C24 1.516(4) . ? C8 C11 1.523(5) . ? C8 C12 1.555(4) . ? C8 H8 1.0000 . ? C9 C12 1.544(4) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 C18 1.375(5) . ? C10 C23 1.408(4) . ? C10 H10 0.9500 . ? C11 C22 1.514(5) . ? C11 H1A 0.9900 . ? C11 H1B 0.9900 . ? C12 H12 1.0000 . ? C13 C16 1.376(5) . ? C13 C30 1.382(5) . ? C13 H13 0.9500 . ? C14 C18 1.375(5) . ? C14 C29 1.383(5) . ? C14 H14 0.9500 . ? C15 C26 1.541(4) . ? C15 H1C 0.9800 . ? C15 H1D 0.9800 . ? C15 H1E 0.9800 . ? C16 C39 1.391(6) . ? C16 C37 1.510(5) . ? C17 H1F 0.9800 . ? C17 H1G 0.9800 . ? C17 H1H 0.9800 . ? C18 H18 0.9500 . ? C19 C30 1.386(5) . ? C19 C35 1.394(4) . ? C20 C26 1.541(4) . ? C20 H2A 0.9800 . ? C20 H2B 0.9800 . ? C20 H2C 0.9800 . ? C21 C25 1.394(4) . ? C21 C34 1.398(5) . ? C21 H21 0.9500 . ? C22 C38 1.383(5) . ? C22 C31 1.394(5) . ? C25 C32 1.405(4) . ? C26 C41 1.541(5) . ? C27 C34 1.369(5) . ? C27 C36 1.374(5) . ? C27 H27 0.9500 . ? C28 C33 1.365(5) . ? C28 C40 1.385(5) . ? C28 H28 0.9500 . ? C29 H29 0.9500 . ? C30 H30 0.9500 . ? C31 C33 1.381(5) . ? C31 H31 0.9500 . ? C32 C36 1.391(5) . ? C32 H32 0.9500 . ? C33 H33 0.9500 . ? C34 H34 0.9500 . ? C35 C39 1.383(5) . ? C35 H35 0.9500 . ? C36 H36 0.9500 . ? C37 H3A 0.9800 . ? C37 H3B 0.9800 . ? C37 H3C 0.9800 . ? C38 C40 1.380(5) . ? C38 H38 0.9500 . ? C39 H39 0.9500 . ? C40 H40 0.9500 . ? C41 H4A 0.9800 . ? C41 H4B 0.9800 . ? C41 H4C 0.9800 . ? 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 O3 S01 N6 111.60(13) . . ? O3 S01 C19 104.30(15) . . ? N6 S01 C19 101.28(15) . . ? C23 Si2 C25 109.44(14) . . ? C23 Si2 C9 106.55(15) . . ? C25 Si2 C9 113.01(13) . . ? C23 Si2 C26 107.55(14) . . ? C25 Si2 C26 110.65(15) . . ? C9 Si2 C26 109.43(15) . . ? C24 O4 C17 115.7(3) . . ? C12 N6 S01 119.6(2) . . ? C12 N6 H19 107(2) . . ? S01 N6 H19 111(2) . . ? C29 C7 C23 122.3(3) . . ? C29 C7 H7 118.9 . . ? C23 C7 H7 118.9 . . ? C24 C8 C11 111.1(3) . . ? C24 C8 C12 109.0(2) . . ? C11 C8 C12 115.7(3) . . ? C24 C8 H8 106.8 . . ? C11 C8 H8 106.8 . . ? C12 C8 H8 106.8 . . ? C12 C9 Si2 123.5(2) . . ? C12 C9 H9A 106.4 . . ? Si2 C9 H9A 106.4 . . ? C12 C9 H9B 106.4 . . ? Si2 C9 H9B 106.4 . . ? H9A C9 H9B 106.5 . . ? C18 C10 C23 122.6(3) . . ? C18 C10 H10 118.7 . . ? C23 C10 H10 118.7 . . ? C22 C11 C8 112.0(3) . . ? C22 C11 H1A 109.2 . . ? C8 C11 H1A 109.2 . . ? C22 C11 H1B 109.2 . . ? C8 C11 H1B 109.2 . . ? H1A C11 H1B 107.9 . . ? N6 C12 C9 110.8(2) . . ? N6 C12 C8 108.3(2) . . ? C9 C12 C8 112.9(2) . . ? N6 C12 H12 108.2 . . ? C9 C12 H12 108.2 . . ? C8 C12 H12 108.2 . . ? C16 C13 C30 121.5(4) . . ? C16 C13 H13 119.3 . . ? C30 C13 H13 119.3 . . ? C18 C14 C29 119.0(3) . . ? C18 C14 H14 120.5 . . ? C29 C14 H14 120.5 . . ? C26 C15 H1C 109.5 . . ? C26 C15 H1D 109.5 . . ? H1C C15 H1D 109.5 . . ? C26 C15 H1E 109.5 . . ? H1C C15 H1E 109.5 . . ? H1D C15 H1E 109.5 . . ? C13 C16 C39 118.5(3) . . ? C13 C16 C37 121.0(4) . . ? C39 C16 C37 120.5(3) . . ? O4 C17 H1F 109.5 . . ? O4 C17 H1G 109.5 . . ? H1F C17 H1G 109.5 . . ? O4 C17 H1H 109.5 . . ? H1F C17 H1H 109.5 . . ? H1G C17 H1H 109.5 . . ? C10 C18 C14 120.5(3) . . ? C10 C18 H18 119.7 . . ? C14 C18 H18 119.7 . . ? C30 C19 C35 120.5(3) . . ? C30 C19 S01 120.6(3) . . ? C35 C19 S01 118.1(3) . . ? C26 C20 H2A 109.5 . . ? C26 C20 H2B 109.5 . . ? H2A C20 H2B 109.5 . . ? C26 C20 H2C 109.5 . . ? H2A C20 H2C 109.5 . . ? H2B C20 H2C 109.5 . . ? C25 C21 C34 121.1(3) . . ? C25 C21 H21 119.4 . . ? C34 C21 H21 119.4 . . ? C38 C22 C31 117.2(3) . . ? C38 C22 C11 122.1(3) . . ? C31 C22 C11 120.7(3) . . ? C7 C23 C10 115.3(3) . . ? C7 C23 Si2 121.5(2) . . ? C10 C23 Si2 123.2(3) . . ? O5 C24 O4 123.8(3) . . ? O5 C24 C8 125.3(3) . . ? O4 C24 C8 110.9(3) . . ? C21 C25 C32 116.5(3) . . ? C21 C25 Si2 123.0(2) . . ? C32 C25 Si2 120.5(2) . . ? C41 C26 C15 108.4(3) . . ? C41 C26 C20 108.6(3) . . ? C15 C26 C20 108.9(3) . . ? C41 C26 Si2 112.4(2) . . ? C15 C26 Si2 109.1(2) . . ? C20 C26 Si2 109.5(2) . . ? C34 C27 C36 120.1(3) . . ? C34 C27 H27 120.0 . . ? C36 C27 H27 120.0 . . ? C33 C28 C40 119.6(3) . . ? C33 C28 H28 120.2 . . ? C40 C28 H28 120.2 . . ? C14 C29 C7 120.3(3) . . ? C14 C29 H29 119.8 . . ? C7 C29 H29 119.8 . . ? C13 C30 C19 119.3(3) . . ? C13 C30 H30 120.4 . . ? C19 C30 H30 120.4 . . ? C33 C31 C22 121.5(3) . . ? C33 C31 H31 119.3 . . ? C22 C31 H31 119.3 . . ? C36 C32 C25 122.1(3) . . ? C36 C32 H32 118.9 . . ? C25 C32 H32 118.9 . . ? C28 C33 C31 120.2(4) . . ? C28 C33 H33 119.9 . . ? C31 C33 H33 119.9 . . ? C27 C34 C21 120.6(3) . . ? C27 C34 H34 119.7 . . ? C21 C34 H34 119.7 . . ? C39 C35 C19 118.7(3) . . ? C39 C35 H35 120.7 . . ? C19 C35 H35 120.7 . . ? C27 C36 C32 119.5(3) . . ? C27 C36 H36 120.2 . . ? C32 C36 H36 120.2 . . ? C16 C37 H3A 109.5 . . ? C16 C37 H3B 109.5 . . ? H3A C37 H3B 109.5 . . ? C16 C37 H3C 109.5 . . ? H3A C37 H3C 109.5 . . ? H3B C37 H3C 109.5 . . ? C40 C38 C22 121.6(3) . . ? C40 C38 H38 119.2 . . ? C22 C38 H38 119.2 . . ? C35 C39 C16 121.5(3) . . ? C35 C39 H39 119.3 . . ? C16 C39 H39 119.3 . . ? C38 C40 C28 119.9(3) . . ? C38 C40 H40 120.1 . . ? C28 C40 H40 120.1 . . ? C26 C41 H4A 109.5 . . ? C26 C41 H4B 109.5 . . ? H4A C41 H4B 109.5 . . ? C26 C41 H4C 109.5 . . ? H4A C41 H4C 109.5 . . ? H4B C41 H4C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O3 S01 N6 C12 -36.7(3) . . . . ? C19 S01 N6 C12 73.8(3) . . . . ? C23 Si2 C9 C12 -154.6(3) . . . . ? C25 Si2 C9 C12 -34.4(3) . . . . ? C26 Si2 C9 C12 89.4(3) . . . . ? C24 C8 C11 C22 64.5(4) . . . . ? C12 C8 C11 C22 -170.6(3) . . . . ? S01 N6 C12 C9 83.6(3) . . . . ? S01 N6 C12 C8 -151.9(2) . . . . ? Si2 C9 C12 N6 -168.1(2) . . . . ? Si2 C9 C12 C8 70.2(4) . . . . ? C24 C8 C12 N6 55.5(3) . . . . ? C11 C8 C12 N6 -70.6(3) . . . . ? C24 C8 C12 C9 178.6(3) . . . . ? C11 C8 C12 C9 52.5(4) . . . . ? C30 C13 C16 C39 -2.1(5) . . . . ? C30 C13 C16 C37 176.0(3) . . . . ? C23 C10 C18 C14 0.1(6) . . . . ? C29 C14 C18 C10 -1.5(6) . . . . ? O3 S01 C19 C30 -5.2(3) . . . . ? N6 S01 C19 C30 -121.2(3) . . . . ? O3 S01 C19 C35 -175.4(2) . . . . ? N6 S01 C19 C35 68.6(3) . . . . ? C8 C11 C22 C38 -128.7(3) . . . . ? C8 C11 C22 C31 52.3(4) . . . . ? C29 C7 C23 C10 -1.8(5) . . . . ? C29 C7 C23 Si2 179.8(3) . . . . ? C18 C10 C23 C7 1.6(5) . . . . ? C18 C10 C23 Si2 180.0(3) . . . . ? C25 Si2 C23 C7 -137.1(3) . . . . ? C9 Si2 C23 C7 -14.6(3) . . . . ? C26 Si2 C23 C7 102.6(3) . . . . ? C25 Si2 C23 C10 44.6(3) . . . . ? C9 Si2 C23 C10 167.1(3) . . . . ? C26 Si2 C23 C10 -75.6(3) . . . . ? C17 O4 C24 O5 -1.8(4) . . . . ? C17 O4 C24 C8 178.0(3) . . . . ? C11 C8 C24 O5 20.9(4) . . . . ? C12 C8 C24 O5 -107.8(4) . . . . ? C11 C8 C24 O4 -158.9(3) . . . . ? C12 C8 C24 O4 72.4(3) . . . . ? C34 C21 C25 C32 0.6(5) . . . . ? C34 C21 C25 Si2 -179.8(3) . . . . ? C23 Si2 C25 C21 3.3(3) . . . . ? C9 Si2 C25 C21 -115.2(3) . . . . ? C26 Si2 C25 C21 121.7(3) . . . . ? C23 Si2 C25 C32 -177.1(3) . . . . ? C9 Si2 C25 C32 64.3(3) . . . . ? C26 Si2 C25 C32 -58.8(3) . . . . ? C23 Si2 C26 C41 -177.2(2) . . . . ? C25 Si2 C26 C41 63.4(2) . . . . ? C9 Si2 C26 C41 -61.8(2) . . . . ? C23 Si2 C26 C15 -56.9(2) . . . . ? C25 Si2 C26 C15 -176.4(2) . . . . ? C9 Si2 C26 C15 58.4(2) . . . . ? C23 Si2 C26 C20 62.1(2) . . . . ? C25 Si2 C26 C20 -57.4(3) . . . . ? C9 Si2 C26 C20 177.5(2) . . . . ? C18 C14 C29 C7 1.3(5) . . . . ? C23 C7 C29 C14 0.4(5) . . . . ? C16 C13 C30 C19 0.8(5) . . . . ? C35 C19 C30 C13 0.9(5) . . . . ? S01 C19 C30 C13 -169.1(2) . . . . ? C38 C22 C31 C33 1.6(5) . . . . ? C11 C22 C31 C33 -179.4(3) . . . . ? C21 C25 C32 C36 -0.1(5) . . . . ? Si2 C25 C32 C36 -179.7(3) . . . . ? C40 C28 C33 C31 -1.4(5) . . . . ? C22 C31 C33 C28 -0.1(6) . . . . ? C36 C27 C34 C21 -0.7(6) . . . . ? C25 C21 C34 C27 -0.3(6) . . . . ? C30 C19 C35 C39 -1.2(5) . . . . ? S01 C19 C35 C39 169.0(3) . . . . ? C34 C27 C36 C32 1.2(5) . . . . ? C25 C32 C36 C27 -0.9(5) . . . . ? C31 C22 C38 C40 -1.7(5) . . . . ? C11 C22 C38 C40 179.3(3) . . . . ? C19 C35 C39 C16 -0.2(5) . . . . ? C13 C16 C39 C35 1.8(5) . . . . ? C37 C16 C39 C35 -176.4(3) . . . . ? C22 C38 C40 C28 0.3(5) . . . . ? C33 C28 C40 C38 1.3(5) . . . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.308 _refine_diff_density_min -0.204 _refine_diff_density_rms 0.051 # Attachment '5b R = p-flurophenyl.cif' data_baru _database_code_depnum_ccdc_archive 'CCDC 859597' #TrackingRef '5b R = p-flurophenyl.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common REUT _chemical_melting_point ? _chemical_formula_moiety 'C34 H38 F N O3 S Si' _chemical_formula_sum 'C34 H38 F N O3 S Si' _chemical_formula_weight 587.82 _chemical_absolute_configuration syn 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' F F 0.0171 0.0103 '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) _symmetry_space_group_name_HALL 'P 2yb' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 8.458(5) _cell_length_b 36.758(5) _cell_length_c 9.963(5) _cell_angle_alpha 90.000(5) _cell_angle_beta 90.409(5) _cell_angle_gamma 90.000(5) _cell_volume 3097(2) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2409 _cell_measurement_theta_min 2.22 _cell_measurement_theta_max 22.87 _exptl_crystal_description cuboid _exptl_crystal_colour colorless _exptl_crystal_size_max 0.086 _exptl_crystal_size_mid 0.061 _exptl_crystal_size_min 0.043 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.261 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1248 _exptl_absorpt_coefficient_mu 0.184 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.567890 _exptl_absorpt_correction_T_max 1 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'BRUKER SMART APEX' _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 18022 _diffrn_reflns_av_R_equivalents 0.0585 _diffrn_reflns_av_sigmaI/netI 0.1077 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -46 _diffrn_reflns_limit_k_max 46 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.33 _diffrn_reflns_theta_max 26.50 _reflns_number_total 11766 _reflns_number_gt 8742 _reflns_threshold_expression >2sigma(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, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0939P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.03(10) _refine_ls_number_reflns 11766 _refine_ls_number_parameters 747 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0930 _refine_ls_R_factor_gt 0.0643 _refine_ls_wR_factor_ref 0.1870 _refine_ls_wR_factor_gt 0.1459 _refine_ls_goodness_of_fit_ref 1.015 _refine_ls_restrained_S_all 1.014 _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 S1 S 0.90927(14) 0.33235(4) 0.86907(13) 0.0243(3) Uani 1 1 d . . . Si1 Si 0.59558(15) 0.57262(4) 0.66959(14) 0.0206(3) Uani 1 1 d . . . S2 S 0.59120(14) 0.58538(4) 1.18091(13) 0.0240(3) Uani 1 1 d . . . Si2 Si 0.90900(15) 0.34542(4) 0.35655(14) 0.0206(3) Uani 1 1 d . . . F1 F 1.3268(3) 0.65969(9) 1.1982(3) 0.0369(8) Uani 1 1 d . . . F2 F 0.1781(3) 0.25834(9) 0.8833(3) 0.0375(8) Uani 1 1 d . . . O3 O 1.0363(4) 0.35732(10) 0.8222(4) 0.0293(9) Uani 1 1 d . . . O5 O 0.7576(4) 0.69127(9) 0.7472(4) 0.0277(8) Uani 1 1 d . . . O4 O 0.4630(4) 0.56101(10) 1.1322(4) 0.0289(8) Uani 1 1 d . . . O1 O 0.7397(4) 0.22727(10) 0.4319(4) 0.0281(8) Uani 1 1 d . . . O2 O 0.9215(4) 0.23833(9) 0.5916(4) 0.0282(8) Uani 1 1 d . . . N2 N 0.6487(5) 0.61543(12) 1.0680(4) 0.0231(9) Uani 1 1 d . . . O6 O 0.5768(4) 0.67964(10) 0.9069(4) 0.0309(9) Uani 1 1 d . . . N1 N 0.8535(5) 0.30214(12) 0.7533(4) 0.0211(9) Uani 1 1 d . . . C10 C 0.5632(6) 0.27254(14) 0.6389(5) 0.0222(10) Uani 1 1 d . . . C11 C 0.5627(6) 0.24580(13) 0.7369(5) 0.0229(11) Uani 1 1 d . . . H11 H 0.6514 0.2311 0.7479 0.027 Uiso 1 1 calc R . . C62 C 0.7658(6) 0.55721(13) 1.1772(5) 0.0204(10) Uani 1 1 d . . . C23 C 0.7143(6) 0.40012(14) 0.4760(5) 0.0234(11) Uani 1 1 d . . . H23 H 0.7597 0.3924 0.5564 0.028 Uiso 1 1 calc R . . C1 C 0.8472(6) 0.30778(14) 0.2400(5) 0.0229(11) Uani 1 1 d . . . C53 C 0.7927(6) 0.63723(14) 0.8700(5) 0.0243(11) Uani 1 1 d . . . H53 H 0.8304 0.6290 0.7822 0.029 Uiso 1 1 calc R . . C22 C 0.7539(6) 0.38180(14) 0.3593(5) 0.0226(11) Uani 1 1 d . . . C64 C 0.8824(6) 0.49825(15) 1.1707(5) 0.0269(12) Uani 1 1 d . . . H64 H 0.8710 0.4731 1.1650 0.032 Uiso 1 1 calc R . . C57 C 1.0704(6) 0.62445(14) 0.9385(5) 0.0264(11) Uani 1 1 d . . . H57 H 1.0722 0.6068 0.8715 0.032 Uiso 1 1 calc R . . C8 C 0.8038(6) 0.24729(14) 0.5290(5) 0.0250(11) Uani 1 1 d . . . C27 C 0.6811(6) 0.39463(14) 0.2402(5) 0.0229(11) Uani 1 1 d . . . H27 H 0.7026 0.3831 0.1594 0.027 Uiso 1 1 calc R . . C63 C 0.7483(6) 0.51992(14) 1.1691(5) 0.0242(11) Uani 1 1 d . . . H63 H 0.6482 0.5095 1.1627 0.029 Uiso 1 1 calc R . . C65 C 1.0320(6) 0.51279(14) 1.1803(5) 0.0243(11) Uani 1 1 d . . . C35 C 0.7527(6) 0.53653(13) 0.6722(5) 0.0211(10) Uani 1 1 d . . . C60 C 1.0681(6) 0.67736(14) 1.1349(5) 0.0263(12) Uani 1 1 d . . . H60 H 1.0694 0.6956 1.1997 0.032 Uiso 1 1 calc R . . C52 C 0.6971(5) 0.60579(13) 0.9296(5) 0.0207(10) Uani 1 1 d . . . H52 H 0.7702 0.5852 0.9382 0.025 Uiso 1 1 calc R . . C30 C 0.4508(6) 0.36646(15) 0.8802(5) 0.0285(12) Uani 1 1 d . . . H30 H 0.3517 0.3559 0.8900 0.034 Uiso 1 1 calc R . . C15 C 0.4300(6) 0.29460(15) 0.6255(6) 0.0311(13) Uani 1 1 d . . . H15 H 0.4284 0.3126 0.5601 0.037 Uiso 1 1 calc R . . C17 C 0.9444(5) 0.32508(13) 0.5290(5) 0.0214(10) Uani 1 1 d . . . H17A H 1.0135 0.3043 0.5173 0.026 Uiso 1 1 calc R . . H17B H 1.0033 0.3429 0.5809 0.026 Uiso 1 1 calc R . . C37 C 0.9070(6) 0.49034(15) 0.7915(6) 0.0306(12) Uani 1 1 d . . . H37 H 0.9397 0.4799 0.8720 0.037 Uiso 1 1 calc R . . C33 C 0.7493(6) 0.39684(14) 0.8551(5) 0.0253(11) Uani 1 1 d . . . H33 H 0.8490 0.4074 0.8495 0.030 Uiso 1 1 calc R . . C26 C 0.5787(6) 0.42397(14) 0.2408(5) 0.0270(12) Uani 1 1 d . . . H26 H 0.5330 0.4320 0.1610 0.032 Uiso 1 1 calc R . . C28 C 0.7342(6) 0.35954(14) 0.8656(5) 0.0232(11) Uani 1 1 d . . . C67 C 0.9162(6) 0.57298(14) 1.1912(5) 0.0241(11) Uani 1 1 d . . . H67 H 0.9269 0.5980 1.2003 0.029 Uiso 1 1 calc R . . C38 C 0.9637(6) 0.47741(15) 0.6718(6) 0.0294(12) Uani 1 1 d . . . H38 H 1.0323 0.4577 0.6714 0.035 Uiso 1 1 calc R . . C51 C 0.5590(6) 0.59249(14) 0.8410(5) 0.0252(11) Uani 1 1 d . . . H51A H 0.4877 0.6129 0.8290 0.030 Uiso 1 1 calc R . . H51B H 0.5023 0.5743 0.8922 0.030 Uiso 1 1 calc R . . C56 C 0.9372(6) 0.64568(13) 0.9538(5) 0.0242(11) Uani 1 1 d . . . C16 C 0.8060(5) 0.31248(13) 0.6165(5) 0.0203(10) Uani 1 1 d . . . H16 H 0.7347 0.3334 0.6251 0.024 Uiso 1 1 calc R . . C12 C 0.4335(6) 0.24049(14) 0.8188(5) 0.0254(12) Uani 1 1 d . . . H12 H 0.4334 0.2223 0.8836 0.030 Uiso 1 1 calc R . . C6 C 0.6929(6) 0.30374(14) 0.1935(5) 0.0251(11) Uani 1 1 d . . . H6 H 0.6184 0.3214 0.2143 0.030 Uiso 1 1 calc R . . C9 C 0.7070(6) 0.28119(13) 0.5534(5) 0.0239(11) Uani 1 1 d . . . H9 H 0.6682 0.2897 0.4660 0.029 Uiso 1 1 calc R . . C58 C 1.1998(6) 0.62881(15) 1.0200(6) 0.0298(12) Uani 1 1 d . . . H58 H 1.2885 0.6142 1.0094 0.036 Uiso 1 1 calc R . . C36 C 0.8000(6) 0.51932(13) 0.7919(5) 0.0251(11) Uani 1 1 d . . . H36 H 0.7591 0.5274 0.8731 0.030 Uiso 1 1 calc R . . C24 C 0.6115(6) 0.42905(14) 0.4790(6) 0.0301(12) Uani 1 1 d . . . H24 H 0.5873 0.4403 0.5600 0.036 Uiso 1 1 calc R . . C39 C 0.9196(6) 0.49346(14) 0.5525(6) 0.0269(12) Uani 1 1 d . . . H39 H 0.9596 0.4848 0.4719 0.032 Uiso 1 1 calc R . . C54 C 0.6938(6) 0.67101(14) 0.8452(5) 0.0229(11) Uani 1 1 d . . . C55 C 0.6745(6) 0.72498(15) 0.7153(6) 0.0355(13) Uani 1 1 d . . . H55A H 0.7288 0.7374 0.6446 0.053 Uiso 1 1 calc R . . H55B H 0.6716 0.7402 0.7936 0.053 Uiso 1 1 calc R . . H55C H 0.5685 0.7195 0.6868 0.053 Uiso 1 1 calc R . . C2 C 0.9525(6) 0.27959(14) 0.2083(5) 0.0294(12) Uani 1 1 d . . . H2 H 1.0565 0.2810 0.2389 0.035 Uiso 1 1 calc R . . C40 C 0.8153(6) 0.52265(13) 0.5523(5) 0.0254(11) Uani 1 1 d . . . H40 H 0.7862 0.5332 0.4711 0.030 Uiso 1 1 calc R . . C31 C 0.4619(6) 0.40361(14) 0.8651(5) 0.0257(11) Uani 1 1 d . . . C14 C 0.2999(5) 0.29020(15) 0.7077(6) 0.0284(12) Uani 1 1 d . . . H14 H 0.2119 0.3052 0.6993 0.034 Uiso 1 1 calc R . . C5 C 0.6470(7) 0.27381(14) 0.1161(5) 0.0294(12) Uani 1 1 d . . . H5 H 0.5439 0.2722 0.0837 0.035 Uiso 1 1 calc R . . C7 C 0.8197(7) 0.19363(15) 0.4004(6) 0.0361(13) Uani 1 1 d . . . H7A H 0.7639 0.1814 0.3294 0.054 Uiso 1 1 calc R . . H7B H 0.8228 0.1784 0.4786 0.054 Uiso 1 1 calc R . . H7C H 0.9257 0.1988 0.3722 0.054 Uiso 1 1 calc R . . C41 C 0.4008(6) 0.55010(14) 0.6154(5) 0.0246(11) Uani 1 1 d . . . C13 C 0.3050(6) 0.26303(15) 0.8016(6) 0.0293(12) Uani 1 1 d . . . C49 C 0.5946(7) 0.66787(15) 0.4450(6) 0.0321(13) Uani 1 1 d . . . H49 H 0.5209 0.6859 0.4251 0.038 Uiso 1 1 calc R . . C29 C 0.5846(6) 0.34425(14) 0.8813(5) 0.0238(11) Uani 1 1 d . . . H29 H 0.5740 0.3193 0.8924 0.029 Uiso 1 1 calc R . . C45 C 0.6571(6) 0.61030(13) 0.5533(5) 0.0230(11) Uani 1 1 d . . . C3 C 0.9057(7) 0.24958(16) 0.1326(6) 0.0359(14) Uani 1 1 d . . . H3 H 0.9782 0.2314 0.1124 0.043 Uiso 1 1 calc R . . C25 C 0.5442(6) 0.44136(15) 0.3601(6) 0.0309(13) Uani 1 1 d . . . H25 H 0.4762 0.4612 0.3605 0.037 Uiso 1 1 calc R . . C46 C 0.8108(6) 0.61392(14) 0.5053(5) 0.0253(11) Uani 1 1 d . . . H46 H 0.8846 0.5959 0.5244 0.030 Uiso 1 1 calc R . . C18 C 1.1023(6) 0.36808(14) 0.3074(5) 0.0245(11) Uani 1 1 d . . . C34 C 0.3171(6) 0.42720(16) 0.8588(6) 0.0363(14) Uani 1 1 d . . . H34A H 0.3480 0.4521 0.8476 0.054 Uiso 1 1 calc R . . H34B H 0.2587 0.4247 0.9406 0.054 Uiso 1 1 calc R . . H34C H 0.2519 0.4199 0.7843 0.054 Uiso 1 1 calc R . . C59 C 1.1967(6) 0.65510(14) 1.1178(5) 0.0251(11) Uani 1 1 d . . . C43 C 0.4023(7) 0.54173(19) 0.4652(6) 0.0465(17) Uani 1 1 d . . . H43A H 0.4932 0.5272 0.4446 0.070 Uiso 1 1 calc R . . H43B H 0.4066 0.5641 0.4155 0.070 Uiso 1 1 calc R . . H43C H 0.3080 0.5287 0.4410 0.070 Uiso 1 1 calc R . . C66 C 1.0482(6) 0.55078(14) 1.1912(5) 0.0259(11) Uani 1 1 d . . . H66 H 1.1484 0.5610 1.1984 0.031 Uiso 1 1 calc R . . C48 C 0.7487(6) 0.67089(15) 0.3980(5) 0.0304(12) Uani 1 1 d . . . H48 H 0.7788 0.6907 0.3463 0.037 Uiso 1 1 calc R . . C61 C 0.9370(6) 0.67211(13) 1.0540(5) 0.0227(11) Uani 1 1 d . . . H61 H 0.8475 0.6864 1.0665 0.027 Uiso 1 1 calc R . . C50 C 0.5510(6) 0.63811(14) 0.5211(5) 0.0277(12) Uani 1 1 d . . . H50 H 0.4477 0.6366 0.5519 0.033 Uiso 1 1 calc R . . C4 C 0.7536(7) 0.24688(14) 0.0880(5) 0.0294(12) Uani 1 1 d . . . H4 H 0.7220 0.2267 0.0384 0.035 Uiso 1 1 calc R . . C47 C 0.8563(7) 0.64375(14) 0.4299(6) 0.0318(13) Uani 1 1 d . . . H47 H 0.9601 0.6456 0.4004 0.038 Uiso 1 1 calc R . . C20 C 1.0939(7) 0.38284(17) 0.1635(6) 0.0380(14) Uani 1 1 d . . . H20A H 1.0782 0.3630 0.1020 0.057 Uiso 1 1 calc R . . H20B H 1.1910 0.3951 0.1428 0.057 Uiso 1 1 calc R . . H20C H 1.0074 0.3996 0.1557 0.057 Uiso 1 1 calc R . . C21 C 1.1307(8) 0.40009(19) 0.4041(7) 0.056(2) Uani 1 1 d . . . H21A H 1.1368 0.3912 0.4946 0.084 Uiso 1 1 calc R . . H21B H 1.0450 0.4171 0.3964 0.084 Uiso 1 1 calc R . . H21C H 1.2281 0.4120 0.3818 0.084 Uiso 1 1 calc R . . C32 C 0.6139(7) 0.41869(15) 0.8530(5) 0.0305(12) Uani 1 1 d . . . H32 H 0.6247 0.4437 0.8435 0.037 Uiso 1 1 calc R . . C68 C 1.1775(6) 0.48875(15) 1.1786(6) 0.0347(13) Uani 1 1 d . . . H68A H 1.2706 0.5036 1.1859 0.052 Uiso 1 1 calc R . . H68B H 1.1801 0.4753 1.0961 0.052 Uiso 1 1 calc R . . H68C H 1.1740 0.4721 1.2528 0.052 Uiso 1 1 calc R . . C42 C 0.3874(7) 0.51328(18) 0.6898(7) 0.0495(18) Uani 1 1 d . . . H42A H 0.4783 0.4986 0.6705 0.074 Uiso 1 1 calc R . . H42B H 0.2935 0.5008 0.6603 0.074 Uiso 1 1 calc R . . H42C H 0.3819 0.5175 0.7847 0.074 Uiso 1 1 calc R . . C44 C 0.2556(6) 0.57363(18) 0.6479(7) 0.0433(16) Uani 1 1 d . . . H44A H 0.2632 0.5964 0.6015 0.065 Uiso 1 1 calc R . . H44B H 0.2519 0.5780 0.7429 0.065 Uiso 1 1 calc R . . H44C H 0.1613 0.5612 0.6198 0.065 Uiso 1 1 calc R . . C19 C 1.2462(7) 0.3424(2) 0.3170(9) 0.062(2) Uani 1 1 d . . . H19A H 1.2536 0.3326 0.4062 0.094 Uiso 1 1 calc R . . H19B H 1.3408 0.3557 0.2972 0.094 Uiso 1 1 calc R . . H19C H 1.2338 0.3229 0.2537 0.094 Uiso 1 1 calc R . . H111 H 0.926(6) 0.2838(14) 0.761(5) 0.020(13) Uiso 1 1 d . . . H100 H 0.599(6) 0.6327(17) 1.078(6) 0.033(18) 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 0.0215(6) 0.0299(7) 0.0214(7) -0.0010(5) -0.0001(5) -0.0001(5) Si1 0.0202(7) 0.0211(7) 0.0205(7) -0.0009(6) -0.0003(5) -0.0010(6) S2 0.0222(6) 0.0298(7) 0.0201(7) 0.0024(5) 0.0023(5) 0.0006(5) Si2 0.0203(7) 0.0214(7) 0.0201(7) 0.0001(5) 0.0011(6) -0.0010(6) F1 0.0270(16) 0.0413(19) 0.042(2) -0.0036(16) -0.0109(14) -0.0016(14) F2 0.0236(15) 0.0422(19) 0.047(2) 0.0064(16) 0.0156(14) -0.0043(14) O3 0.0241(18) 0.033(2) 0.031(2) -0.0049(17) -0.0010(16) -0.0037(16) O5 0.0265(18) 0.0245(19) 0.032(2) 0.0061(16) 0.0060(16) 0.0027(15) O4 0.0240(18) 0.034(2) 0.029(2) 0.0069(16) 0.0013(16) -0.0041(16) O1 0.0279(18) 0.0274(19) 0.029(2) -0.0071(16) 0.0003(16) 0.0021(16) O2 0.0266(19) 0.027(2) 0.031(2) -0.0005(16) -0.0024(16) -0.0002(15) N2 0.022(2) 0.025(2) 0.022(2) -0.0003(19) 0.0027(18) 0.005(2) O6 0.031(2) 0.034(2) 0.028(2) 0.0023(17) 0.0046(17) 0.0071(17) N1 0.0186(19) 0.026(2) 0.018(2) -0.0015(18) 0.0002(17) 0.0025(18) C10 0.025(2) 0.025(3) 0.016(2) -0.003(2) 0.001(2) 0.002(2) C11 0.025(2) 0.020(3) 0.024(3) 0.000(2) -0.001(2) 0.001(2) C62 0.025(2) 0.022(2) 0.014(2) -0.002(2) -0.002(2) 0.001(2) C23 0.024(2) 0.032(3) 0.014(2) -0.001(2) -0.001(2) -0.001(2) C1 0.024(2) 0.027(3) 0.018(2) -0.001(2) 0.004(2) -0.003(2) C53 0.023(2) 0.027(3) 0.023(3) -0.004(2) 0.002(2) -0.001(2) C22 0.025(3) 0.023(3) 0.021(3) 0.001(2) 0.004(2) -0.002(2) C64 0.030(3) 0.028(3) 0.023(3) 0.008(2) 0.002(2) -0.003(2) C57 0.022(2) 0.031(3) 0.026(3) -0.002(2) 0.005(2) 0.001(2) C8 0.022(2) 0.031(3) 0.022(3) 0.004(2) 0.002(2) -0.006(2) C27 0.023(2) 0.025(3) 0.021(3) 0.002(2) 0.000(2) -0.003(2) C63 0.024(3) 0.030(3) 0.019(3) 0.005(2) 0.001(2) -0.003(2) C65 0.026(3) 0.029(3) 0.018(3) 0.005(2) -0.005(2) 0.005(2) C35 0.023(2) 0.024(3) 0.016(2) -0.004(2) 0.003(2) -0.001(2) C60 0.035(3) 0.018(3) 0.025(3) -0.001(2) -0.001(2) -0.002(2) C52 0.024(2) 0.025(3) 0.014(2) -0.002(2) -0.0056(19) 0.002(2) C30 0.025(3) 0.032(3) 0.029(3) -0.001(2) 0.001(2) -0.005(2) C15 0.029(3) 0.031(3) 0.033(3) 0.008(2) 0.001(2) -0.002(2) C17 0.016(2) 0.025(3) 0.023(3) -0.002(2) -0.001(2) -0.003(2) C37 0.034(3) 0.026(3) 0.031(3) 0.005(2) -0.008(2) -0.001(2) C33 0.030(3) 0.027(3) 0.020(3) 0.000(2) 0.007(2) -0.001(2) C26 0.027(3) 0.030(3) 0.024(3) 0.009(2) -0.002(2) 0.002(2) C28 0.025(3) 0.030(3) 0.015(2) -0.003(2) 0.000(2) 0.001(2) C67 0.028(3) 0.022(3) 0.022(3) -0.004(2) 0.002(2) -0.001(2) C38 0.024(3) 0.022(3) 0.042(3) -0.001(2) 0.002(2) 0.001(2) C51 0.030(3) 0.020(3) 0.025(3) -0.002(2) -0.003(2) -0.001(2) C56 0.026(3) 0.025(3) 0.022(3) 0.001(2) 0.005(2) -0.004(2) C16 0.019(2) 0.027(3) 0.015(2) 0.002(2) -0.0018(19) -0.001(2) C12 0.024(3) 0.025(3) 0.027(3) -0.002(2) 0.004(2) -0.007(2) C6 0.031(3) 0.026(3) 0.018(3) 0.002(2) 0.002(2) 0.000(2) C9 0.025(2) 0.025(3) 0.022(3) 0.004(2) 0.003(2) 0.006(2) C58 0.017(2) 0.038(3) 0.035(3) -0.005(2) 0.002(2) 0.003(2) C36 0.028(3) 0.023(3) 0.024(3) -0.002(2) 0.003(2) -0.004(2) C24 0.033(3) 0.027(3) 0.031(3) -0.005(2) 0.008(2) 0.002(2) C39 0.026(3) 0.027(3) 0.028(3) -0.002(2) 0.008(2) 0.001(2) C54 0.019(2) 0.028(3) 0.022(3) 0.001(2) -0.001(2) -0.004(2) C55 0.035(3) 0.028(3) 0.044(4) 0.011(3) -0.002(3) 0.003(3) C2 0.032(3) 0.032(3) 0.025(3) -0.001(2) 0.008(2) 0.008(2) C40 0.031(3) 0.020(3) 0.026(3) 0.001(2) 0.005(2) -0.004(2) C31 0.030(3) 0.025(3) 0.023(3) -0.002(2) 0.006(2) 0.000(2) C14 0.014(2) 0.035(3) 0.036(3) 0.001(2) 0.001(2) 0.005(2) C5 0.036(3) 0.028(3) 0.024(3) 0.007(2) -0.004(2) -0.005(2) C7 0.039(3) 0.024(3) 0.045(4) -0.004(3) 0.004(3) 0.007(2) C41 0.021(2) 0.026(3) 0.026(3) 0.000(2) 0.000(2) -0.003(2) C13 0.023(3) 0.033(3) 0.032(3) 0.001(2) 0.005(2) -0.004(2) C49 0.041(3) 0.026(3) 0.029(3) 0.006(2) 0.005(3) 0.011(3) C29 0.026(2) 0.023(3) 0.023(3) 0.001(2) 0.004(2) 0.001(2) C45 0.030(3) 0.021(3) 0.018(3) -0.004(2) 0.000(2) -0.002(2) C3 0.043(3) 0.031(3) 0.034(3) -0.008(3) 0.000(3) 0.008(3) C25 0.025(3) 0.022(3) 0.045(4) 0.000(2) 0.002(3) -0.002(2) C46 0.027(3) 0.026(3) 0.024(3) 0.002(2) 0.002(2) -0.002(2) C18 0.027(3) 0.027(3) 0.020(3) -0.001(2) -0.001(2) -0.004(2) C34 0.029(3) 0.038(3) 0.042(4) 0.004(3) 0.004(3) 0.006(3) C59 0.020(2) 0.026(3) 0.029(3) 0.002(2) -0.005(2) -0.005(2) C43 0.043(3) 0.062(4) 0.035(4) -0.020(3) 0.000(3) -0.014(3) C66 0.024(2) 0.030(3) 0.023(3) 0.000(2) 0.000(2) 0.001(2) C48 0.044(3) 0.027(3) 0.021(3) 0.004(2) 0.006(2) -0.003(2) C61 0.023(2) 0.022(3) 0.022(3) 0.002(2) -0.004(2) 0.002(2) C50 0.029(3) 0.032(3) 0.022(3) 0.002(2) 0.003(2) 0.003(2) C4 0.048(3) 0.021(3) 0.019(3) -0.005(2) 0.002(2) -0.004(2) C47 0.035(3) 0.032(3) 0.029(3) -0.003(2) 0.008(2) -0.003(3) C20 0.035(3) 0.044(3) 0.035(3) 0.011(3) 0.004(3) -0.007(3) C21 0.062(4) 0.067(5) 0.040(4) -0.018(3) 0.027(3) -0.048(4) C32 0.045(3) 0.022(3) 0.025(3) 0.003(2) 0.004(2) -0.002(3) C68 0.032(3) 0.031(3) 0.041(4) 0.002(3) -0.001(3) 0.003(3) C42 0.041(3) 0.053(4) 0.055(4) 0.024(3) -0.011(3) -0.020(3) C44 0.017(3) 0.050(4) 0.063(4) -0.018(3) 0.003(3) -0.005(3) C19 0.023(3) 0.062(5) 0.102(6) 0.043(4) 0.005(4) -0.001(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 O3 1.491(4) . ? S1 N1 1.667(4) . ? S1 C28 1.787(5) . ? Si1 C35 1.878(5) . ? Si1 C45 1.882(5) . ? Si1 C51 1.885(5) . ? Si1 C41 1.918(5) . ? S2 O4 1.485(4) . ? S2 N2 1.652(4) . ? S2 C62 1.804(5) . ? Si2 C22 1.873(5) . ? Si2 C1 1.878(5) . ? Si2 C17 1.896(5) . ? Si2 C18 1.902(5) . ? F1 C59 1.367(6) . ? F2 C13 1.363(6) . ? O5 C54 1.344(6) . ? O5 C55 1.458(6) . ? O1 C8 1.328(6) . ? O1 C7 1.445(6) . ? O2 C8 1.217(6) . ? N2 C52 1.484(6) . ? N2 H100 0.77(6) . ? O6 C54 1.211(6) . ? N1 C16 1.469(6) . ? N1 H111 0.92(5) . ? C10 C11 1.386(7) . ? C10 C15 1.393(7) . ? C10 C9 1.524(7) . ? C11 C12 1.382(6) . ? C11 H11 0.9300 . ? C62 C63 1.381(7) . ? C62 C67 1.404(7) . ? C23 C24 1.374(7) . ? C23 C22 1.386(7) . ? C23 H23 0.9300 . ? C1 C6 1.390(7) . ? C1 C2 1.404(7) . ? C53 C56 1.507(7) . ? C53 C54 1.516(7) . ? C53 C52 1.533(7) . ? C53 H53 0.9800 . ? C22 C27 1.414(7) . ? C64 C65 1.376(7) . ? C64 C63 1.386(7) . ? C64 H64 0.9300 . ? C57 C58 1.368(7) . ? C57 C56 1.380(7) . ? C57 H57 0.9300 . ? C8 C9 1.512(7) . ? C27 C26 1.383(7) . ? C27 H27 0.9300 . ? C63 H63 0.9300 . ? C65 C66 1.407(7) . ? C65 C68 1.515(7) . ? C35 C36 1.405(7) . ? C35 C40 1.406(7) . ? C60 C59 1.372(7) . ? C60 C61 1.380(7) . ? C60 H60 0.9300 . ? C52 C51 1.538(7) . ? C52 H52 0.9800 . ? C30 C31 1.377(7) . ? C30 C29 1.395(7) . ? C30 H30 0.9300 . ? C15 C14 1.385(7) . ? C15 H15 0.9300 . ? C17 C16 1.536(6) . ? C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? C37 C38 1.373(8) . ? C37 C36 1.398(7) . ? C37 H37 0.9300 . ? C33 C28 1.381(7) . ? C33 C32 1.399(8) . ? C33 H33 0.9300 . ? C26 C25 1.382(8) . ? C26 H26 0.9300 . ? C28 C29 1.394(7) . ? C67 C66 1.383(7) . ? C67 H67 0.9300 . ? C38 C39 1.376(8) . ? C38 H38 0.9300 . ? C51 H51A 0.9700 . ? C51 H51B 0.9700 . ? C56 C61 1.393(7) . ? C16 C9 1.552(7) . ? C16 H16 0.9800 . ? C12 C13 1.377(7) . ? C12 H12 0.9300 . ? C6 C5 1.397(7) . ? C6 H6 0.9300 . ? C9 H9 0.9800 . ? C58 C59 1.372(7) . ? C58 H58 0.9300 . ? C36 H36 0.9300 . ? C24 C25 1.387(8) . ? C24 H24 0.9300 . ? C39 C40 1.389(7) . ? C39 H39 0.9300 . ? C55 H55A 0.9600 . ? C55 H55B 0.9600 . ? C55 H55C 0.9600 . ? C2 C3 1.393(8) . ? C2 H2 0.9300 . ? C40 H40 0.9300 . ? C31 C32 1.406(8) . ? C31 C34 1.502(7) . ? C14 C13 1.369(7) . ? C14 H14 0.9300 . ? C5 C4 1.369(8) . ? C5 H5 0.9300 . ? C7 H7A 0.9600 . ? C7 H7B 0.9600 . ? C7 H7C 0.9600 . ? C41 C43 1.528(7) . ? C41 C44 1.538(7) . ? C41 C42 1.548(8) . ? C49 C50 1.383(7) . ? C49 C48 1.392(7) . ? C49 H49 0.9300 . ? C29 H29 0.9300 . ? C45 C46 1.395(7) . ? C45 C50 1.396(7) . ? C3 C4 1.362(8) . ? C3 H3 0.9300 . ? C25 H25 0.9300 . ? C46 C47 1.385(7) . ? C46 H46 0.9300 . ? C18 C20 1.534(7) . ? C18 C21 1.539(8) . ? C18 C19 1.543(8) . ? C34 H34A 0.9600 . ? C34 H34B 0.9600 . ? C34 H34C 0.9600 . ? C43 H43A 0.9600 . ? C43 H43B 0.9600 . ? C43 H43C 0.9600 . ? C66 H66 0.9300 . ? C48 C47 1.386(8) . ? C48 H48 0.9300 . ? C61 H61 0.9300 . ? C50 H50 0.9300 . ? C4 H4 0.9300 . ? C47 H47 0.9300 . ? C20 H20A 0.9600 . ? C20 H20B 0.9600 . ? C20 H20C 0.9600 . ? C21 H21A 0.9600 . ? C21 H21B 0.9600 . ? C21 H21C 0.9600 . ? C32 H32 0.9300 . ? C68 H68A 0.9600 . ? C68 H68B 0.9600 . ? C68 H68C 0.9600 . ? C42 H42A 0.9600 . ? C42 H42B 0.9600 . ? C42 H42C 0.9600 . ? C44 H44A 0.9600 . ? C44 H44B 0.9600 . ? C44 H44C 0.9600 . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? 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 O3 S1 N1 113.2(2) . . ? O3 S1 C28 104.4(2) . . ? N1 S1 C28 97.4(2) . . ? C35 Si1 C45 109.2(2) . . ? C35 Si1 C51 112.4(2) . . ? C45 Si1 C51 108.7(2) . . ? C35 Si1 C41 107.8(2) . . ? C45 Si1 C41 112.6(2) . . ? C51 Si1 C41 106.0(2) . . ? O4 S2 N2 113.5(2) . . ? O4 S2 C62 104.1(2) . . ? N2 S2 C62 97.2(2) . . ? C22 Si2 C1 110.1(2) . . ? C22 Si2 C17 112.0(2) . . ? C1 Si2 C17 108.1(2) . . ? C22 Si2 C18 107.1(2) . . ? C1 Si2 C18 113.5(2) . . ? C17 Si2 C18 106.0(2) . . ? C54 O5 C55 115.7(4) . . ? C8 O1 C7 116.3(4) . . ? C52 N2 S2 123.9(4) . . ? C52 N2 H100 118(5) . . ? S2 N2 H100 107(4) . . ? C16 N1 S1 123.0(3) . . ? C16 N1 H111 116(3) . . ? S1 N1 H111 104(3) . . ? C11 C10 C15 118.3(5) . . ? C11 C10 C9 123.2(4) . . ? C15 C10 C9 118.2(4) . . ? C12 C11 C10 121.5(5) . . ? C12 C11 H11 119.3 . . ? C10 C11 H11 119.3 . . ? C63 C62 C67 120.8(5) . . ? C63 C62 S2 118.9(4) . . ? C67 C62 S2 120.1(4) . . ? C24 C23 C22 123.5(5) . . ? C24 C23 H23 118.3 . . ? C22 C23 H23 118.3 . . ? C6 C1 C2 116.2(5) . . ? C6 C1 Si2 122.8(4) . . ? C2 C1 Si2 120.6(4) . . ? C56 C53 C54 111.4(4) . . ? C56 C53 C52 111.6(4) . . ? C54 C53 C52 112.9(4) . . ? C56 C53 H53 106.8 . . ? C54 C53 H53 106.8 . . ? C52 C53 H53 106.8 . . ? C23 C22 C27 115.8(5) . . ? C23 C22 Si2 122.2(4) . . ? C27 C22 Si2 121.8(4) . . ? C65 C64 C63 122.0(5) . . ? C65 C64 H64 119.0 . . ? C63 C64 H64 119.0 . . ? C58 C57 C56 121.3(5) . . ? C58 C57 H57 119.4 . . ? C56 C57 H57 119.4 . . ? O2 C8 O1 123.5(5) . . ? O2 C8 C9 125.6(5) . . ? O1 C8 C9 110.8(4) . . ? C26 C27 C22 121.7(5) . . ? C26 C27 H27 119.1 . . ? C22 C27 H27 119.1 . . ? C62 C63 C64 118.8(5) . . ? C62 C63 H63 120.6 . . ? C64 C63 H63 120.6 . . ? C64 C65 C66 118.7(5) . . ? C64 C65 C68 121.3(5) . . ? C66 C65 C68 120.1(5) . . ? C36 C35 C40 116.8(5) . . ? C36 C35 Si1 121.8(4) . . ? C40 C35 Si1 121.0(4) . . ? C59 C60 C61 118.6(5) . . ? C59 C60 H60 120.7 . . ? C61 C60 H60 120.7 . . ? N2 C52 C53 109.3(4) . . ? N2 C52 C51 113.3(4) . . ? C53 C52 C51 114.7(4) . . ? N2 C52 H52 106.3 . . ? C53 C52 H52 106.3 . . ? C51 C52 H52 106.3 . . ? C31 C30 C29 121.7(5) . . ? C31 C30 H30 119.2 . . ? C29 C30 H30 119.2 . . ? C14 C15 C10 121.4(5) . . ? C14 C15 H15 119.3 . . ? C10 C15 H15 119.3 . . ? C16 C17 Si2 121.1(3) . . ? C16 C17 H17A 107.0 . . ? Si2 C17 H17A 107.0 . . ? C16 C17 H17B 107.0 . . ? Si2 C17 H17B 107.0 . . ? H17A C17 H17B 106.8 . . ? C38 C37 C36 119.8(5) . . ? C38 C37 H37 120.1 . . ? C36 C37 H37 120.1 . . ? C28 C33 C32 119.7(5) . . ? C28 C33 H33 120.2 . . ? C32 C33 H33 120.2 . . ? C25 C26 C27 120.0(5) . . ? C25 C26 H26 120.0 . . ? C27 C26 H26 120.0 . . ? C33 C28 C29 119.6(5) . . ? C33 C28 S1 118.7(4) . . ? C29 C28 S1 121.7(4) . . ? C66 C67 C62 119.2(5) . . ? C66 C67 H67 120.4 . . ? C62 C67 H67 120.4 . . ? C37 C38 C39 120.5(5) . . ? C37 C38 H38 119.7 . . ? C39 C38 H38 119.7 . . ? C52 C51 Si1 120.9(3) . . ? C52 C51 H51A 107.1 . . ? Si1 C51 H51A 107.1 . . ? C52 C51 H51B 107.1 . . ? Si1 C51 H51B 107.1 . . ? H51A C51 H51B 106.8 . . ? C57 C56 C61 118.6(5) . . ? C57 C56 C53 118.8(5) . . ? C61 C56 C53 122.4(4) . . ? N1 C16 C17 113.6(4) . . ? N1 C16 C9 109.1(4) . . ? C17 C16 C9 113.9(4) . . ? N1 C16 H16 106.6 . . ? C17 C16 H16 106.6 . . ? C9 C16 H16 106.6 . . ? C13 C12 C11 117.9(5) . . ? C13 C12 H12 121.0 . . ? C11 C12 H12 121.0 . . ? C1 C6 C5 121.7(5) . . ? C1 C6 H6 119.2 . . ? C5 C6 H6 119.2 . . ? C8 C9 C10 110.7(4) . . ? C8 C9 C16 112.6(4) . . ? C10 C9 C16 111.0(4) . . ? C8 C9 H9 107.4 . . ? C10 C9 H9 107.4 . . ? C16 C9 H9 107.4 . . ? C57 C58 C59 119.0(5) . . ? C57 C58 H58 120.5 . . ? C59 C58 H58 120.5 . . ? C37 C36 C35 121.4(5) . . ? C37 C36 H36 119.3 . . ? C35 C36 H36 119.3 . . ? C23 C24 C25 119.3(5) . . ? C23 C24 H24 120.4 . . ? C25 C24 H24 120.4 . . ? C38 C39 C40 120.0(5) . . ? C38 C39 H39 120.0 . . ? C40 C39 H39 120.0 . . ? O6 C54 O5 123.9(5) . . ? O6 C54 C53 125.7(5) . . ? O5 C54 C53 110.4(4) . . ? O5 C55 H55A 109.5 . . ? O5 C55 H55B 109.5 . . ? H55A C55 H55B 109.5 . . ? O5 C55 H55C 109.5 . . ? H55A C55 H55C 109.5 . . ? H55B C55 H55C 109.5 . . ? C3 C2 C1 121.9(5) . . ? C3 C2 H2 119.1 . . ? C1 C2 H2 119.1 . . ? C39 C40 C35 121.5(5) . . ? C39 C40 H40 119.3 . . ? C35 C40 H40 119.3 . . ? C30 C31 C32 117.6(5) . . ? C30 C31 C34 121.4(5) . . ? C32 C31 C34 121.0(5) . . ? C13 C14 C15 117.9(5) . . ? C13 C14 H14 121.1 . . ? C15 C14 H14 121.1 . . ? C4 C5 C6 120.1(5) . . ? C4 C5 H5 119.9 . . ? C6 C5 H5 119.9 . . ? O1 C7 H7A 109.5 . . ? O1 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? O1 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C43 C41 C44 109.4(5) . . ? C43 C41 C42 107.1(5) . . ? C44 C41 C42 109.2(5) . . ? C43 C41 Si1 110.5(4) . . ? C44 C41 Si1 112.5(4) . . ? C42 C41 Si1 107.9(4) . . ? F2 C13 C14 118.7(5) . . ? F2 C13 C12 118.3(5) . . ? C14 C13 C12 123.1(5) . . ? C50 C49 C48 120.1(5) . . ? C50 C49 H49 120.0 . . ? C48 C49 H49 120.0 . . ? C28 C29 C30 120.0(5) . . ? C28 C29 H29 120.0 . . ? C30 C29 H29 120.0 . . ? C46 C45 C50 116.8(5) . . ? C46 C45 Si1 123.0(4) . . ? C50 C45 Si1 120.0(4) . . ? C4 C3 C2 119.9(5) . . ? C4 C3 H3 120.0 . . ? C2 C3 H3 120.0 . . ? C26 C25 C24 119.7(5) . . ? C26 C25 H25 120.1 . . ? C24 C25 H25 120.1 . . ? C47 C46 C45 121.6(5) . . ? C47 C46 H46 119.2 . . ? C45 C46 H46 119.2 . . ? C20 C18 C21 108.7(5) . . ? C20 C18 C19 107.8(5) . . ? C21 C18 C19 108.0(5) . . ? C20 C18 Si2 111.2(4) . . ? C21 C18 Si2 107.7(4) . . ? C19 C18 Si2 113.3(4) . . ? C31 C34 H34A 109.5 . . ? C31 C34 H34B 109.5 . . ? H34A C34 H34B 109.5 . . ? C31 C34 H34C 109.5 . . ? H34A C34 H34C 109.5 . . ? H34B C34 H34C 109.5 . . ? F1 C59 C60 119.2(5) . . ? F1 C59 C58 118.9(4) . . ? C60 C59 C58 121.8(5) . . ? C41 C43 H43A 109.5 . . ? C41 C43 H43B 109.5 . . ? H43A C43 H43B 109.5 . . ? C41 C43 H43C 109.5 . . ? H43A C43 H43C 109.5 . . ? H43B C43 H43C 109.5 . . ? C67 C66 C65 120.5(5) . . ? C67 C66 H66 119.8 . . ? C65 C66 H66 119.8 . . ? C47 C48 C49 118.7(5) . . ? C47 C48 H48 120.6 . . ? C49 C48 H48 120.6 . . ? C60 C61 C56 120.7(5) . . ? C60 C61 H61 119.6 . . ? C56 C61 H61 119.6 . . ? C49 C50 C45 122.1(5) . . ? C49 C50 H50 118.9 . . ? C45 C50 H50 118.9 . . ? C3 C4 C5 120.2(5) . . ? C3 C4 H4 119.9 . . ? C5 C4 H4 119.9 . . ? C46 C47 C48 120.6(5) . . ? C46 C47 H47 119.7 . . ? C48 C47 H47 119.7 . . ? C18 C20 H20A 109.5 . . ? C18 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C18 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C18 C21 H21A 109.5 . . ? C18 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C18 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C33 C32 C31 121.4(5) . . ? C33 C32 H32 119.3 . . ? C31 C32 H32 119.3 . . ? C65 C68 H68A 109.5 . . ? C65 C68 H68B 109.5 . . ? H68A C68 H68B 109.5 . . ? C65 C68 H68C 109.5 . . ? H68A C68 H68C 109.5 . . ? H68B C68 H68C 109.5 . . ? C41 C42 H42A 109.5 . . ? C41 C42 H42B 109.5 . . ? H42A C42 H42B 109.5 . . ? C41 C42 H42C 109.5 . . ? H42A C42 H42C 109.5 . . ? H42B C42 H42C 109.5 . . ? C41 C44 H44A 109.5 . . ? C41 C44 H44B 109.5 . . ? H44A C44 H44B 109.5 . . ? C41 C44 H44C 109.5 . . ? H44A C44 H44C 109.5 . . ? H44B C44 H44C 109.5 . . ? C18 C19 H19A 109.5 . . ? C18 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C18 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O4 S2 N2 C52 -52.4(5) . . . . ? C62 S2 N2 C52 56.3(4) . . . . ? O3 S1 N1 C16 -52.3(4) . . . . ? C28 S1 N1 C16 56.9(4) . . . . ? C15 C10 C11 C12 0.9(7) . . . . ? C9 C10 C11 C12 175.3(5) . . . . ? O4 S2 C62 C63 -16.8(4) . . . . ? N2 S2 C62 C63 -133.3(4) . . . . ? O4 S2 C62 C67 167.3(4) . . . . ? N2 S2 C62 C67 50.8(4) . . . . ? C22 Si2 C1 C6 -15.6(5) . . . . ? C17 Si2 C1 C6 107.0(4) . . . . ? C18 Si2 C1 C6 -135.7(4) . . . . ? C22 Si2 C1 C2 172.1(4) . . . . ? C17 Si2 C1 C2 -65.3(4) . . . . ? C18 Si2 C1 C2 52.0(5) . . . . ? C24 C23 C22 C27 -0.1(7) . . . . ? C24 C23 C22 Si2 174.0(4) . . . . ? C1 Si2 C22 C23 141.9(4) . . . . ? C17 Si2 C22 C23 21.6(5) . . . . ? C18 Si2 C22 C23 -94.2(4) . . . . ? C1 Si2 C22 C27 -44.3(5) . . . . ? C17 Si2 C22 C27 -164.6(4) . . . . ? C18 Si2 C22 C27 79.6(4) . . . . ? C7 O1 C8 O2 -1.3(7) . . . . ? C7 O1 C8 C9 -178.9(4) . . . . ? C23 C22 C27 C26 0.9(7) . . . . ? Si2 C22 C27 C26 -173.3(4) . . . . ? C67 C62 C63 C64 -2.0(7) . . . . ? S2 C62 C63 C64 -177.9(4) . . . . ? C65 C64 C63 C62 0.1(8) . . . . ? C63 C64 C65 C66 1.1(8) . . . . ? C63 C64 C65 C68 -178.5(5) . . . . ? C45 Si1 C35 C36 138.6(4) . . . . ? C51 Si1 C35 C36 17.9(5) . . . . ? C41 Si1 C35 C36 -98.7(4) . . . . ? C45 Si1 C35 C40 -48.8(5) . . . . ? C51 Si1 C35 C40 -169.5(4) . . . . ? C41 Si1 C35 C40 73.9(5) . . . . ? S2 N2 C52 C53 -161.4(3) . . . . ? S2 N2 C52 C51 69.4(5) . . . . ? C56 C53 C52 N2 58.6(5) . . . . ? C54 C53 C52 N2 -67.9(5) . . . . ? C56 C53 C52 C51 -173.0(4) . . . . ? C54 C53 C52 C51 60.6(5) . . . . ? C11 C10 C15 C14 0.1(8) . . . . ? C9 C10 C15 C14 -174.7(5) . . . . ? C22 Si2 C17 C16 48.8(4) . . . . ? C1 Si2 C17 C16 -72.7(4) . . . . ? C18 Si2 C17 C16 165.3(4) . . . . ? C22 C27 C26 C25 -0.5(8) . . . . ? C32 C33 C28 C29 -3.5(8) . . . . ? C32 C33 C28 S1 -179.6(4) . . . . ? O3 S1 C28 C33 -14.9(5) . . . . ? N1 S1 C28 C33 -131.2(4) . . . . ? O3 S1 C28 C29 169.1(4) . . . . ? N1 S1 C28 C29 52.7(5) . . . . ? C63 C62 C67 C66 2.6(7) . . . . ? S2 C62 C67 C66 178.5(4) . . . . ? C36 C37 C38 C39 2.0(8) . . . . ? N2 C52 C51 Si1 -171.5(3) . . . . ? C53 C52 C51 Si1 62.1(5) . . . . ? C35 Si1 C51 C52 49.6(4) . . . . ? C45 Si1 C51 C52 -71.5(4) . . . . ? C41 Si1 C51 C52 167.1(4) . . . . ? C58 C57 C56 C61 0.5(8) . . . . ? C58 C57 C56 C53 -174.2(5) . . . . ? C54 C53 C56 C57 -151.8(5) . . . . ? C52 C53 C56 C57 81.0(6) . . . . ? C54 C53 C56 C61 33.7(7) . . . . ? C52 C53 C56 C61 -93.4(6) . . . . ? S1 N1 C16 C17 71.9(5) . . . . ? S1 N1 C16 C9 -159.9(3) . . . . ? Si2 C17 C16 N1 -172.1(3) . . . . ? Si2 C17 C16 C9 62.2(5) . . . . ? C10 C11 C12 C13 -0.9(8) . . . . ? C2 C1 C6 C5 -1.9(7) . . . . ? Si2 C1 C6 C5 -174.5(4) . . . . ? O2 C8 C9 C10 -97.9(6) . . . . ? O1 C8 C9 C10 79.6(5) . . . . ? O2 C8 C9 C16 27.0(7) . . . . ? O1 C8 C9 C16 -155.5(4) . . . . ? C11 C10 C9 C8 32.4(7) . . . . ? C15 C10 C9 C8 -153.2(5) . . . . ? C11 C10 C9 C16 -93.5(6) . . . . ? C15 C10 C9 C16 80.9(6) . . . . ? N1 C16 C9 C8 -67.4(5) . . . . ? C17 C16 C9 C8 60.6(5) . . . . ? N1 C16 C9 C10 57.4(5) . . . . ? C17 C16 C9 C10 -174.6(4) . . . . ? C56 C57 C58 C59 -0.6(8) . . . . ? C38 C37 C36 C35 -2.3(8) . . . . ? C40 C35 C36 C37 1.5(7) . . . . ? Si1 C35 C36 C37 174.4(4) . . . . ? C22 C23 C24 C25 -1.0(8) . . . . ? C37 C38 C39 C40 -0.9(8) . . . . ? C55 O5 C54 O6 -1.3(7) . . . . ? C55 O5 C54 C53 -179.0(4) . . . . ? C56 C53 C54 O6 -98.6(6) . . . . ? C52 C53 C54 O6 27.9(7) . . . . ? C56 C53 C54 O5 79.0(5) . . . . ? C52 C53 C54 O5 -154.5(4) . . . . ? C6 C1 C2 C3 1.1(8) . . . . ? Si2 C1 C2 C3 173.9(4) . . . . ? C38 C39 C40 C35 0.1(8) . . . . ? C36 C35 C40 C39 -0.4(7) . . . . ? Si1 C35 C40 C39 -173.4(4) . . . . ? C29 C30 C31 C32 -1.1(8) . . . . ? C29 C30 C31 C34 177.7(5) . . . . ? C10 C15 C14 C13 -1.0(8) . . . . ? C1 C6 C5 C4 2.2(8) . . . . ? C35 Si1 C41 C43 -74.0(4) . . . . ? C45 Si1 C41 C43 46.6(5) . . . . ? C51 Si1 C41 C43 165.4(4) . . . . ? C35 Si1 C41 C44 163.4(4) . . . . ? C45 Si1 C41 C44 -76.0(5) . . . . ? C51 Si1 C41 C44 42.8(5) . . . . ? C35 Si1 C41 C42 42.8(4) . . . . ? C45 Si1 C41 C42 163.4(4) . . . . ? C51 Si1 C41 C42 -77.8(4) . . . . ? C15 C14 C13 F2 179.9(5) . . . . ? C15 C14 C13 C12 1.0(8) . . . . ? C11 C12 C13 F2 -179.0(5) . . . . ? C11 C12 C13 C14 0.0(8) . . . . ? C33 C28 C29 C30 2.9(8) . . . . ? S1 C28 C29 C30 178.9(4) . . . . ? C31 C30 C29 C28 -0.6(8) . . . . ? C35 Si1 C45 C46 -14.1(5) . . . . ? C51 Si1 C45 C46 109.0(4) . . . . ? C41 Si1 C45 C46 -133.8(4) . . . . ? C35 Si1 C45 C50 171.9(4) . . . . ? C51 Si1 C45 C50 -65.1(4) . . . . ? C41 Si1 C45 C50 52.1(5) . . . . ? C1 C2 C3 C4 -0.6(8) . . . . ? C27 C26 C25 C24 -0.6(8) . . . . ? C23 C24 C25 C26 1.4(8) . . . . ? C50 C45 C46 C47 0.3(7) . . . . ? Si1 C45 C46 C47 -173.9(4) . . . . ? C22 Si2 C18 C20 -65.3(4) . . . . ? C1 Si2 C18 C20 56.5(4) . . . . ? C17 Si2 C18 C20 175.0(4) . . . . ? C22 Si2 C18 C21 53.8(5) . . . . ? C1 Si2 C18 C21 175.5(4) . . . . ? C17 Si2 C18 C21 -66.0(5) . . . . ? C22 Si2 C18 C19 173.1(5) . . . . ? C1 Si2 C18 C19 -65.1(5) . . . . ? C17 Si2 C18 C19 53.4(5) . . . . ? C61 C60 C59 F1 -179.3(4) . . . . ? C61 C60 C59 C58 2.2(8) . . . . ? C57 C58 C59 F1 -179.3(5) . . . . ? C57 C58 C59 C60 -0.8(8) . . . . ? C62 C67 C66 C65 -1.4(8) . . . . ? C64 C65 C66 C67 -0.4(8) . . . . ? C68 C65 C66 C67 179.2(5) . . . . ? C50 C49 C48 C47 -0.4(8) . . . . ? C59 C60 C61 C56 -2.3(8) . . . . ? C57 C56 C61 C60 1.0(7) . . . . ? C53 C56 C61 C60 175.5(5) . . . . ? C48 C49 C50 C45 -0.2(8) . . . . ? C46 C45 C50 C49 0.3(8) . . . . ? Si1 C45 C50 C49 174.7(4) . . . . ? C2 C3 C4 C5 0.8(8) . . . . ? C6 C5 C4 C3 -1.6(8) . . . . ? C45 C46 C47 C48 -0.9(8) . . . . ? C49 C48 C47 C46 1.0(8) . . . . ? C28 C33 C32 C31 1.8(8) . . . . ? C30 C31 C32 C33 0.5(8) . . . . ? C34 C31 C32 C33 -178.3(5) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 26.50 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.607 _refine_diff_density_min -0.466 _refine_diff_density_rms 0.087