# Supplementary Material (ESI) for ChemComm # This journal is © The Royal Society of Chemistry 1999 # CCDC Number: 182/1352 data_anti-5 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H32 O2 Si' _chemical_formula_weight 380.59 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' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M P212121 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 7.900(3) _cell_length_b 14.751(5) _cell_length_c 18.956(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2209.0(13) _cell_formula_units_Z 4 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.144 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 824 _exptl_absorpt_coefficient_mu 0.121 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 200(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 'Area detector (IPDS, STOE)' _diffrn_measurement_method 'Image plate' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10267 _diffrn_reflns_av_R_equivalents 0.0912 _diffrn_reflns_av_sigmaI/netI 0.0715 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.55 _diffrn_reflns_theta_max 25.82 _reflns_number_total 4228 _reflns_number_gt 3964 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'STOE IPDS software' _computing_cell_refinement 'STOE IPDS software' _computing_data_reduction 'STOE IPDS software' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SCHAKAL-97 (Keller Freiburg 1997' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme 'calc w=1/[\s^2^(Fo^2^)+(0.0974P)^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 -0.10(14) _refine_ls_number_reflns 4228 _refine_ls_number_parameters 249 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0552 _refine_ls_R_factor_gt 0.0523 _refine_ls_wR_factor_ref 0.1421 _refine_ls_wR_factor_gt 0.1392 _refine_ls_goodness_of_fit_ref 1.059 _refine_ls_restrained_S_all 1.059 _refine_ls_shift/su_max 0.005 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.2385(3) 0.05168(17) 0.64179(11) 0.0374(5) Uani 1 d . . . C2 C 0.1727(3) 0.04830(15) 0.71990(10) 0.0309(4) Uani 1 d . . . H2 H 0.2568 0.0156 0.7500 0.037 Uiso 1 calc R . . C3 C 0.2040(3) 0.15104(17) 0.72472(12) 0.0415(5) Uani 1 d . . . H3A H 0.0998 0.1878 0.7199 0.050 Uiso 1 calc R . . H3B H 0.2693 0.1694 0.7670 0.050 Uiso 1 calc R . . C4 C 0.3103(5) 0.1468(2) 0.65720(15) 0.0623(9) Uani 1 d . . . H4A H 0.4338 0.1474 0.6658 0.075 Uiso 1 calc R . . H4B H 0.2784 0.1929 0.6216 0.075 Uiso 1 calc R . . C5 C 0.3741(3) -0.0166(2) 0.62446(11) 0.0449(6) Uani 1 d . . . O1 O 0.5091(3) 0.00036(19) 0.59973(14) 0.0787(7) Uani 1 d . . . O2 O 0.3253(3) -0.10089(13) 0.64044(11) 0.0531(5) Uani 1 d . . . C6 C 0.4476(5) -0.1713(3) 0.6266(2) 0.0752(10) Uani 1 d . . . H6A H 0.4888 -0.1658 0.5781 0.113 Uiso 1 calc R . . H6B H 0.3943 -0.2307 0.6331 0.113 Uiso 1 calc R . . H6C H 0.5428 -0.1652 0.6594 0.113 Uiso 1 calc R . . C7 C 0.1018(4) 0.0488(2) 0.58572(11) 0.0461(6) Uani 1 d . . . H7A H 0.1516 0.0625 0.5396 0.069 Uiso 1 calc R . . H7B H 0.0144 0.0938 0.5967 0.069 Uiso 1 calc R . . H7C H 0.0509 -0.0118 0.5846 0.069 Uiso 1 calc R . . C8 C -0.0046(3) 0.01253(15) 0.73531(10) 0.0306(4) Uani 1 d . . . H8A H -0.0207 -0.0454 0.7098 0.037 Uiso 1 calc R . . H8B H -0.0887 0.0563 0.7169 0.037 Uiso 1 calc R . . Si Si -0.04697(7) -0.00675(4) 0.83190(2) 0.02648(17) Uani 1 d . . . C9 C -0.2831(3) -0.02710(17) 0.84590(12) 0.0380(5) Uani 1 d . . . C10 C -0.3381(4) -0.1022(3) 0.7959(2) 0.0741(10) Uani 1 d . . . H10A H -0.4590 -0.1144 0.8025 0.111 Uiso 1 calc R . . H10B H -0.2731 -0.1573 0.8059 0.111 Uiso 1 calc R . . H10C H -0.3177 -0.0832 0.7471 0.111 Uiso 1 calc R . . C11 C -0.3220(4) -0.0555(4) 0.92139(18) 0.0909(14) Uani 1 d . . . H11A H -0.2974 -0.0051 0.9534 0.136 Uiso 1 calc R . . H11B H -0.2517 -0.1078 0.9341 0.136 Uiso 1 calc R . . H11C H -0.4418 -0.0720 0.9253 0.136 Uiso 1 calc R . . C12 C -0.3880(4) 0.0563(2) 0.8282(2) 0.0681(9) Uani 1 d . . . H12A H -0.5086 0.0410 0.8307 0.102 Uiso 1 calc R . . H12B H -0.3604 0.0769 0.7804 0.102 Uiso 1 calc R . . H12C H -0.3628 0.1046 0.8620 0.102 Uiso 1 calc R . . C13 C 0.0734(3) -0.11009(14) 0.86036(10) 0.0298(4) Uani 1 d . . . C14 C 0.1580(3) -0.16555(15) 0.81184(11) 0.0345(5) Uani 1 d . . . H14 H 0.1565 -0.1494 0.7633 0.041 Uiso 1 calc R . . C15 C 0.2434(3) -0.24295(16) 0.83206(15) 0.0419(5) Uani 1 d . . . H15 H 0.2996 -0.2787 0.7975 0.050 Uiso 1 calc R . . C16 C 0.2481(3) -0.26901(17) 0.90217(16) 0.0460(6) Uani 1 d . . . H16 H 0.3066 -0.3223 0.9162 0.055 Uiso 1 calc R . . C17 C 0.1662(4) -0.21595(18) 0.95113(13) 0.0490(6) Uani 1 d . . . H17 H 0.1682 -0.2332 0.9994 0.059 Uiso 1 calc R . . C18 C 0.0814(3) -0.13837(17) 0.93163(11) 0.0405(5) Uani 1 d . . . H18 H 0.0269 -0.1030 0.9668 0.049 Uiso 1 calc R . . C19 C 0.0350(3) 0.09531(15) 0.88094(9) 0.0313(4) Uani 1 d . . . C20 C 0.1758(3) 0.09041(18) 0.92528(12) 0.0414(5) Uani 1 d . . . H20 H 0.2258 0.0331 0.9347 0.050 Uiso 1 calc R . . C21 C 0.2438(4) 0.1676(2) 0.95586(14) 0.0558(7) Uani 1 d . . . H21 H 0.3403 0.1627 0.9855 0.067 Uiso 1 calc R . . C22 C 0.1725(4) 0.2513(2) 0.94353(15) 0.0564(8) Uani 1 d . . . H22 H 0.2187 0.3038 0.9652 0.068 Uiso 1 calc R . . C23 C 0.0345(4) 0.25861(17) 0.89988(14) 0.0500(6) Uani 1 d . . . H23 H -0.0150 0.3162 0.8910 0.060 Uiso 1 calc R . . C24 C -0.0325(3) 0.18111(16) 0.86870(13) 0.0409(5) Uani 1 d . . . H24 H -0.1272 0.1869 0.8381 0.049 Uiso 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 C1 0.0470(13) 0.0420(12) 0.0233(9) 0.0003(9) 0.0089(9) -0.0030(10) C2 0.0363(10) 0.0371(11) 0.0192(8) -0.0001(8) 0.0020(8) -0.0014(9) C3 0.0521(14) 0.0394(12) 0.0331(11) -0.0047(9) 0.0080(10) -0.0076(10) C4 0.090(2) 0.0524(16) 0.0448(14) -0.0068(12) 0.0280(15) -0.0262(15) C5 0.0424(13) 0.0664(17) 0.0260(10) -0.0084(11) 0.0036(9) -0.0007(12) O1 0.0509(12) 0.099(2) 0.0864(16) 0.0076(15) 0.0288(12) 0.0007(12) O2 0.0479(10) 0.0484(10) 0.0630(11) -0.0135(9) 0.0109(9) 0.0067(9) C6 0.067(2) 0.078(2) 0.081(2) -0.0283(18) -0.0044(19) 0.0275(19) C7 0.0586(15) 0.0562(15) 0.0235(9) 0.0053(10) 0.0037(10) 0.0158(12) C8 0.0347(10) 0.0359(11) 0.0212(8) 0.0013(8) -0.0015(7) -0.0011(8) Si 0.0303(3) 0.0301(3) 0.0190(3) 0.0010(2) 0.00011(19) 0.0001(2) C9 0.0313(11) 0.0489(14) 0.0338(11) 0.0082(9) 0.0028(8) -0.0019(9) C10 0.0496(17) 0.073(2) 0.100(3) -0.028(2) 0.0082(17) -0.0228(16) C11 0.0474(16) 0.171(4) 0.0544(18) 0.037(2) 0.0216(16) 0.000(2) C12 0.0342(13) 0.0637(18) 0.106(3) 0.018(2) 0.0020(16) 0.0040(12) C13 0.0329(11) 0.0322(10) 0.0245(8) 0.0006(8) -0.0025(8) -0.0008(8) C14 0.0380(11) 0.0346(11) 0.0308(10) -0.0017(8) -0.0016(9) 0.0005(9) C15 0.0406(12) 0.0394(12) 0.0456(12) -0.0055(11) -0.0033(11) 0.0049(9) C16 0.0483(14) 0.0377(12) 0.0519(14) 0.0082(11) -0.0138(12) 0.0054(11) C17 0.0663(17) 0.0456(14) 0.0352(12) 0.0095(10) -0.0126(12) 0.0018(13) C18 0.0554(14) 0.0428(12) 0.0235(10) 0.0037(9) -0.0018(9) 0.0051(11) C19 0.0365(11) 0.0375(11) 0.0200(8) -0.0009(7) 0.0046(8) -0.0022(9) C20 0.0456(13) 0.0469(13) 0.0315(10) -0.0017(10) -0.0053(10) -0.0040(11) C21 0.0569(16) 0.071(2) 0.0392(12) -0.0129(13) -0.0046(12) -0.0185(14) C22 0.0706(18) 0.0515(16) 0.0471(14) -0.0234(13) 0.0166(14) -0.0230(14) C23 0.0645(16) 0.0385(13) 0.0471(14) -0.0100(11) 0.0190(13) 0.0000(12) C24 0.0468(13) 0.0372(12) 0.0388(11) -0.0040(9) 0.0059(10) -0.0009(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 C1 C5 1.507(4) . ? C1 C7 1.516(4) . ? C1 C4 1.541(4) . ? C1 C2 1.570(3) . ? C2 C8 1.525(3) . ? C2 C3 1.538(3) . ? C3 C4 1.532(3) . ? C5 O1 1.191(3) . ? C5 O2 1.336(4) . ? O2 C6 1.442(4) . ? C8 Si 1.883(2) . ? Si C13 1.876(2) . ? Si C19 1.884(2) . ? Si C9 1.908(2) . ? C9 C12 1.521(4) . ? C9 C10 1.521(4) . ? C9 C11 1.522(4) . ? C13 C14 1.401(3) . ? C13 C18 1.415(3) . ? C14 C15 1.381(3) . ? C15 C16 1.384(4) . ? C16 C17 1.376(4) . ? C17 C18 1.377(4) . ? C19 C24 1.393(3) . ? C19 C20 1.396(3) . ? C20 C21 1.386(4) . ? C21 C22 1.376(5) . ? C22 C23 1.373(5) . ? C23 C24 1.392(4) . ? 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 C5 C1 C7 109.6(2) . . ? C5 C1 C4 112.9(2) . . ? C7 C1 C4 114.9(2) . . ? C5 C1 C2 114.8(2) . . ? C7 C1 C2 115.10(19) . . ? C4 C1 C2 88.40(17) . . ? C8 C2 C3 118.5(2) . . ? C8 C2 C1 119.72(18) . . ? C3 C2 C1 88.37(17) . . ? C4 C3 C2 89.91(18) . . ? C3 C4 C1 89.65(19) . . ? O1 C5 O2 122.9(3) . . ? O1 C5 C1 125.6(3) . . ? O2 C5 C1 111.5(2) . . ? C5 O2 C6 115.8(3) . . ? C2 C8 Si 113.67(14) . . ? C13 Si C8 108.20(9) . . ? C13 Si C19 109.46(9) . . ? C8 Si C19 107.34(9) . . ? C13 Si C9 109.14(10) . . ? C8 Si C9 109.43(10) . . ? C19 Si C9 113.15(10) . . ? C12 C9 C10 107.2(3) . . ? C12 C9 C11 108.7(3) . . ? C10 C9 C11 109.1(3) . . ? C12 C9 Si 112.03(17) . . ? C10 C9 Si 107.88(18) . . ? C11 C9 Si 111.8(2) . . ? C14 C13 C18 115.7(2) . . ? C14 C13 Si 121.85(16) . . ? C18 C13 Si 122.45(17) . . ? C15 C14 C13 122.3(2) . . ? C14 C15 C16 120.6(2) . . ? C17 C16 C15 118.5(2) . . ? C16 C17 C18 121.4(2) . . ? C17 C18 C13 121.5(2) . . ? C24 C19 C20 116.9(2) . . ? C24 C19 Si 120.80(17) . . ? C20 C19 Si 121.98(18) . . ? C21 C20 C19 121.2(3) . . ? C22 C21 C20 120.5(3) . . ? C23 C22 C21 119.9(2) . . ? C22 C23 C24 119.5(3) . . ? C23 C24 C19 122.0(2) . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 25.82 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.570 _refine_diff_density_min -0.511 _refine_diff_density_rms 0.064