data_3ac _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C13 H16 O S Si' _chemical_formula_weight 248.41 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' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Si' 'Si' 0.0817 0.0704 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'S' 'S' 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 7.310(5) _cell_length_b 15.202(11) _cell_length_c 12.490(9) _cell_angle_alpha 90.00 _cell_angle_beta 92.609(14) _cell_angle_gamma 90.00 _cell_volume 1386.5(17) _cell_formula_units_Z 4 _cell_measurement_temperature 273(2) _cell_measurement_reflns_used 1487 _cell_measurement_theta_min 2.68 _cell_measurement_theta_max 20.86 _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.1 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.190 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 528 _exptl_absorpt_coefficient_mu 0.298 _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 273(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 8340 _diffrn_reflns_av_R_equivalents 0.0436 _diffrn_reflns_av_sigmaI/netI 0.0560 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.11 _diffrn_reflns_theta_max 27.45 _reflns_number_total 3054 _reflns_number_gt 1677 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1210P)^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_number_reflns 3054 _refine_ls_number_parameters 149 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1184 _refine_ls_R_factor_gt 0.0696 _refine_ls_wR_factor_ref 0.2254 _refine_ls_wR_factor_gt 0.1927 _refine_ls_goodness_of_fit_ref 1.040 _refine_ls_restrained_S_all 1.040 _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 O1 O 0.2295(4) 0.79101(15) 0.36903(17) 0.0992(9) Uani 1 1 d . . . C1 C 0.2471(4) 0.94360(18) 0.3692(2) 0.0674(8) Uani 1 1 d . . . C2 C 0.2363(4) 0.8595(2) 0.4248(2) 0.0693(8) Uani 1 1 d . . . C3 C 0.2324(4) 0.8516(2) 0.5410(2) 0.0694(8) Uani 1 1 d . . . C4 C 0.2536(4) 1.0230(2) 0.4223(3) 0.0777(9) Uani 1 1 d . . . C5 C 0.2357(4) 0.9242(3) 0.6031(3) 0.0816(10) Uani 1 1 d . . . C6 C 0.2642(5) 1.1020(2) 0.3622(4) 0.1067(13) Uani 1 1 d . . . H6 H 0.2670 1.1560 0.3973 0.128 Uiso 1 1 calc R . . C7 C 0.2540(5) 0.9450(2) 0.2581(3) 0.0897(10) Uani 1 1 d . . . H7 H 0.2495 0.8919 0.2211 0.108 Uiso 1 1 calc R . . C8 C 0.2293(6) 0.9242(4) 0.7247(3) 0.1230(16) Uani 1 1 d . . . H8A H 0.1167 0.8980 0.7453 0.185 Uiso 1 1 calc R . . H8B H 0.2363 0.9836 0.7507 0.185 Uiso 1 1 calc R . . H8C H 0.3308 0.8910 0.7549 0.185 Uiso 1 1 calc R . . C9 C 0.0149(6) 0.6798(3) 0.5228(3) 0.1086(13) Uani 1 1 d . . . H9A H 0.0006 0.6959 0.4485 0.163 Uiso 1 1 calc R . . H9B H -0.0899 0.6992 0.5599 0.163 Uiso 1 1 calc R . . H9C H 0.0256 0.6170 0.5287 0.163 Uiso 1 1 calc R . . C10 C 0.2701(6) 1.0989(3) 0.2549(5) 0.1277(17) Uani 1 1 d . . . H10 H 0.2766 1.1510 0.2163 0.153 Uiso 1 1 calc R . . C11 C 0.2668(7) 1.0204(3) 0.2019(4) 0.1221(16) Uani 1 1 d . . . H11 H 0.2733 1.0188 0.1278 0.147 Uiso 1 1 calc R . . C12 C 0.2129(10) 0.7128(4) 0.7290(4) 0.188(3) Uani 1 1 d . . . H12A H 0.1939 0.6513 0.7418 0.281 Uiso 1 1 calc R . . H12B H 0.1134 0.7459 0.7563 0.281 Uiso 1 1 calc R . . H12C H 0.3258 0.7311 0.7645 0.281 Uiso 1 1 calc R . . C13 C 0.4322(6) 0.6761(3) 0.5393(4) 0.1383(18) Uani 1 1 d . . . H13A H 0.4104 0.6139 0.5352 0.207 Uiso 1 1 calc R . . H13B H 0.5321 0.6876 0.5899 0.207 Uiso 1 1 calc R . . H13C H 0.4623 0.6976 0.4700 0.207 Uiso 1 1 calc R . . S1 S 0.24657(12) 1.03189(6) 0.55900(9) 0.0925(4) Uani 1 1 d . . . Si1 Si 0.22398(16) 0.73224(7) 0.58289(8) 0.0911(4) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.173(3) 0.0537(14) 0.0723(14) -0.0082(11) 0.0173(14) -0.0039(14) C1 0.0691(19) 0.0501(16) 0.083(2) -0.0002(14) 0.0099(15) 0.0011(13) C2 0.085(2) 0.0488(17) 0.0744(19) -0.0053(13) 0.0073(15) 0.0007(14) C3 0.072(2) 0.0675(19) 0.0683(17) -0.0044(14) -0.0018(13) 0.0052(15) C4 0.069(2) 0.0524(19) 0.112(3) -0.0073(16) 0.0106(17) 0.0018(14) C5 0.071(2) 0.091(3) 0.082(2) -0.0215(18) -0.0039(15) 0.0084(17) C6 0.097(3) 0.052(2) 0.173(4) -0.002(2) 0.027(3) -0.0019(18) C7 0.114(3) 0.071(2) 0.086(2) 0.0140(17) 0.0200(19) 0.0025(19) C8 0.136(4) 0.151(4) 0.081(3) -0.033(3) -0.002(2) 0.007(3) C9 0.124(3) 0.089(3) 0.116(3) 0.005(2) 0.027(2) -0.013(2) C10 0.135(4) 0.088(3) 0.163(5) 0.044(3) 0.045(3) 0.008(3) C11 0.155(4) 0.088(3) 0.126(4) 0.036(3) 0.040(3) 0.008(3) C12 0.323(9) 0.148(5) 0.090(3) 0.047(3) -0.012(4) -0.011(5) C13 0.135(4) 0.079(3) 0.199(5) 0.014(3) -0.023(3) 0.023(3) S1 0.0868(7) 0.0683(6) 0.1220(8) -0.0375(5) 0.0010(5) 0.0029(4) Si1 0.1189(10) 0.0729(7) 0.0807(7) 0.0160(5) -0.0029(6) 0.0024(5) _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 O1 C2 1.253(4) . ? C1 C4 1.377(4) . ? C1 C7 1.390(5) . ? C1 C2 1.459(4) . ? C2 C3 1.458(4) . ? C3 C5 1.350(5) . ? C3 Si1 1.889(4) . ? C4 C6 1.420(5) . ? C4 S1 1.716(4) . ? C5 C8 1.521(4) . ? C5 S1 1.730(4) . ? C6 C10 1.344(7) . ? C7 C11 1.350(5) . ? C9 Si1 1.853(4) . ? C10 C11 1.365(7) . ? C12 Si1 1.854(5) . ? C13 Si1 1.849(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 C4 C1 C7 117.8(3) . . ? C4 C1 C2 122.7(3) . . ? C7 C1 C2 119.6(3) . . ? O1 C2 C3 118.9(3) . . ? O1 C2 C1 117.7(3) . . ? C3 C2 C1 123.4(3) . . ? C5 C3 C2 120.2(3) . . ? C5 C3 Si1 128.8(3) . . ? C2 C3 Si1 110.9(2) . . ? C1 C4 C6 119.2(4) . . ? C1 C4 S1 123.1(3) . . ? C6 C4 S1 117.6(3) . . ? C3 C5 C8 125.0(4) . . ? C3 C5 S1 126.2(3) . . ? C8 C5 S1 108.8(3) . . ? C10 C6 C4 120.2(4) . . ? C11 C7 C1 122.5(4) . . ? C6 C10 C11 120.9(4) . . ? C7 C11 C10 119.4(5) . . ? C4 S1 C5 104.27(15) . . ? C13 Si1 C9 110.9(2) . . ? C13 Si1 C12 106.8(3) . . ? C9 Si1 C12 105.0(3) . . ? C13 Si1 C3 108.91(19) . . ? C9 Si1 C3 109.75(16) . . ? C12 Si1 C3 115.4(2) . . ? _diffrn_measured_fraction_theta_max 0.962 _diffrn_reflns_theta_full 27.45 _diffrn_measured_fraction_theta_full 0.962 _refine_diff_density_max 0.380 _refine_diff_density_min -0.273 _refine_diff_density_rms 0.067