data_shelxl _audit_creation_method SHELXL-97 _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H32 O3 Si' _chemical_formula_weight 360.56 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 'P 21 21 21 ' _symmetry_Int_Tables_number 19 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x+1/2, -y, z+1/2' _cell_length_a 9.5916(4) _cell_length_b 11.3171(5) _cell_length_c 18.2254(8) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1978.35(15) _cell_formula_units_Z 4 _cell_measurement_temperature 143(1) _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.18 _exptl_crystal_density_diffrn 1.211 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 784 _exptl_absorpt_coefficient_mu 0.135 _exptl_absorpt_correction_type 'multi-scan' _exptl_absorpt_process_details '(SADABS; Sheldrick, 2007)' _exptl_absorpt_correction_T_min 0.6911 _exptl_absorpt_correction_T_max 0.7452 _diffrn_ambient_temperature 143(1) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'CCD Area Detector' _diffrn_measurement_device_type 'Bruker APEXII' _diffrn_measurement_method 'phi and omega scans' _diffrn_reflns_number 30835 _diffrn_reflns_av_R_equivalents 0.0314 _diffrn_reflns_av_sigmaI/netI 0.0192 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.12 _diffrn_reflns_theta_max 25.14 _reflns_number_total 3543 _reflns_number_gt 3429 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0435P)^2^+0.3812P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _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 0.11(10) _refine_ls_number_reflns 3543 _refine_ls_number_parameters 231 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0288 _refine_ls_R_factor_gt 0.0278 _refine_ls_wR_factor_ref 0.0762 _refine_ls_wR_factor_gt 0.0756 _refine_ls_goodness_of_fit_ref 1.051 _refine_ls_restrained_S_all 1.051 _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_symetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.52044(17) 0.51978(15) 0.34842(8) 0.0321(4) Uani 1 1 d . . . H1a H 0.5217 0.6055 0.3484 0.043 Uiso 1 1 calc R . . H1b H 0.4693 0.4944 0.3915 0.043 Uiso 1 1 calc R . . C2 C 0.44319(16) 0.47741(13) 0.28039(8) 0.0278(3) Uani 1 1 d . . . H2 H 0.4434 0.3908 0.2815 0.037 Uiso 1 1 calc R . . C3 C 0.51306(14) 0.51550(11) 0.20786(7) 0.0212(3) Uani 1 1 d . . . C4 C 0.66587(14) 0.46686(12) 0.20245(8) 0.0214(3) Uani 1 1 d . . . H4 H 0.6554 0.3807 0.2023 0.028 Uiso 1 1 calc R . . C5 C 0.73211(14) 0.49650(13) 0.12653(7) 0.0225(3) Uani 1 1 d . . . H5 H 0.8140 0.5454 0.1371 0.030 Uiso 1 1 calc R . . C6 C 0.63209(16) 0.57570(12) 0.08098(8) 0.0235(3) Uani 1 1 d . . . C7 C 0.48988(14) 0.50994(13) 0.06767(7) 0.0235(3) Uani 1 1 d . . . C8 C 0.44794(15) 0.45484(12) 0.14121(8) 0.0235(3) Uani 1 1 d . . . C9 C 0.50556(16) 0.41801(14) 0.00527(8) 0.0295(3) Uani 1 1 d . . . C10 C 0.5845(2) 0.30378(15) 0.01287(10) 0.0433(4) Uani 1 1 d . . . H10a H 0.6373 0.2929 -0.0320 0.058 Uiso 1 1 calc R . . H10b H 0.5161 0.2408 0.0148 0.058 Uiso 1 1 calc R . . C11 C 0.68466(19) 0.28435(14) 0.07633(9) 0.0337(4) Uani 1 1 d . . . H11a H 0.7363 0.2120 0.0675 0.045 Uiso 1 1 calc R . . H11b H 0.6307 0.2733 0.1208 0.045 Uiso 1 1 calc R . . C12 C 0.78824(17) 0.38415(13) 0.08891(8) 0.0297(3) Uani 1 1 d . . . H12a H 0.8268 0.4067 0.0417 0.040 Uiso 1 1 calc R . . H12b H 0.8644 0.3536 0.1184 0.040 Uiso 1 1 calc R . . C13 C 0.51603(15) 0.65061(12) 0.19759(8) 0.0237(3) Uani 1 1 d . . . H13a H 0.5551 0.6873 0.2411 0.031 Uiso 1 1 calc R . . H13b H 0.4216 0.6797 0.1914 0.031 Uiso 1 1 calc R . . C14 C 0.60392(16) 0.68472(12) 0.13007(8) 0.0244(3) Uani 1 1 d . . . H14a H 0.6919 0.7181 0.1461 0.032 Uiso 1 1 calc R . . H14b H 0.5550 0.7444 0.1019 0.032 Uiso 1 1 calc R . . C15 C 0.85136(19) 0.64960(15) 0.28861(10) 0.0397(4) Uani 1 1 d . . . H15a H 0.7791 0.7077 0.2936 0.060 Uiso 1 1 calc R . . H15b H 0.9017 0.6632 0.2439 0.060 Uiso 1 1 calc R . . H15c H 0.9141 0.6553 0.3295 0.060 Uiso 1 1 calc R . . C16 C 0.91047(18) 0.38613(16) 0.29630(10) 0.0398(4) Uani 1 1 d . . . H16a H 0.9582 0.3974 0.3421 0.060 Uiso 1 1 calc R . . H16b H 0.9757 0.3934 0.2566 0.060 Uiso 1 1 calc R . . H16c H 0.8691 0.3089 0.2954 0.060 Uiso 1 1 calc R . . C17 C 0.29055(16) 0.51761(16) 0.28545(9) 0.0378(4) Uani 1 1 d . . . H17a H 0.2492 0.4861 0.3292 0.057 Uiso 1 1 calc R . . H17b H 0.2402 0.4896 0.2434 0.057 Uiso 1 1 calc R . . H17c H 0.2868 0.6023 0.2869 0.057 Uiso 1 1 calc R . . C18 C 0.70002(18) 0.61694(14) 0.00951(8) 0.0324(4) Uani 1 1 d . . . H18a H 0.7851 0.6580 0.0204 0.049 Uiso 1 1 calc R . . H18b H 0.6376 0.6690 -0.0160 0.049 Uiso 1 1 calc R . . H18c H 0.7201 0.5497 -0.0208 0.049 Uiso 1 1 calc R . . C19 C 0.37065(16) 0.59626(14) 0.04413(9) 0.0303(3) Uani 1 1 d . . . H19a H 0.3663 0.6606 0.0792 0.040 Uiso 1 1 calc R . . H19b H 0.3942 0.6299 -0.0032 0.040 Uiso 1 1 calc R . . C20 C 0.22989(18) 0.54066(16) 0.03892(10) 0.0413(4) Uani 1 1 d . . . H20 H 0.2197 0.4770 0.0071 0.055 Uiso 1 1 calc R . . C21 C 0.1215(2) 0.5740(2) 0.07503(13) 0.0565(5) Uani 1 1 d . . . H21a H 0.1276 0.6373 0.1074 0.075 Uiso 1 1 calc R . . H21b H 0.0372 0.5347 0.0688 0.075 Uiso 1 1 calc R . . O1 O 0.66066(12) 0.47773(11) 0.35393(6) 0.0388(3) Uani 1 1 d . . . O2 O 0.37674(12) 0.36660(9) 0.14433(6) 0.0340(3) Uani 1 1 d . . . O3 O 0.45467(14) 0.43917(12) -0.05448(6) 0.0430(3) Uani 1 1 d . . . Si1 Si 0.77234(4) 0.49960(4) 0.28640(2) 0.02731(11) 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 0.0382(8) 0.0362(9) 0.0217(7) 0.0025(6) 0.0087(6) 0.0059(7) C2 0.0340(8) 0.0229(7) 0.0265(7) 0.0009(6) 0.0102(6) -0.0007(6) C3 0.0239(6) 0.0174(6) 0.0222(7) 0.0008(6) 0.0041(5) -0.0005(5) C4 0.0252(7) 0.0167(6) 0.0223(7) -0.0003(5) 0.0040(6) 0.0022(5) C5 0.0245(6) 0.0224(6) 0.0207(7) -0.0023(6) 0.0039(5) -0.0029(6) C6 0.0294(7) 0.0211(7) 0.0201(7) 0.0004(6) 0.0032(6) -0.0033(6) C7 0.0272(7) 0.0208(7) 0.0225(7) -0.0008(6) -0.0002(5) -0.0013(6) C8 0.0224(7) 0.0193(6) 0.0287(8) 0.0004(6) 0.0026(6) 0.0001(6) C9 0.0281(8) 0.0312(8) 0.0291(8) -0.0056(7) 0.0019(6) -0.0070(6) C10 0.0588(12) 0.0317(9) 0.0395(9) -0.0137(7) -0.0061(8) 0.0014(8) C11 0.0456(9) 0.0227(7) 0.0327(8) -0.0080(6) 0.0035(7) 0.0053(7) C12 0.0317(8) 0.0308(8) 0.0268(7) -0.0037(6) 0.0076(7) 0.0051(7) C13 0.0292(7) 0.0184(7) 0.0233(7) -0.0014(5) 0.0023(6) 0.0016(6) C14 0.0310(8) 0.0173(6) 0.0249(7) 0.0015(6) 0.0010(6) -0.0034(6) C15 0.0440(10) 0.0392(9) 0.0360(9) -0.0077(8) -0.0101(8) -0.0002(8) C16 0.0371(9) 0.0417(9) 0.0406(9) 0.0005(8) -0.0058(8) 0.0126(7) C17 0.0313(8) 0.0458(10) 0.0363(9) -0.0043(8) 0.0116(7) -0.0040(7) C18 0.0421(9) 0.0311(8) 0.0241(7) 0.0039(6) 0.0054(7) -0.0079(7) C19 0.0327(8) 0.0287(7) 0.0295(8) 0.0009(7) -0.0041(7) 0.0030(7) C20 0.0345(8) 0.0366(9) 0.0527(11) -0.0084(8) -0.0116(8) 0.0026(7) C21 0.0378(10) 0.0553(12) 0.0763(15) -0.0072(11) 0.0053(10) -0.0020(9) O1 0.0406(6) 0.0545(8) 0.0213(5) 0.0070(5) 0.0022(5) 0.0138(6) O2 0.0373(6) 0.0269(5) 0.0378(6) -0.0004(5) 0.0040(5) -0.0121(5) O3 0.0476(7) 0.0547(8) 0.0266(6) -0.0075(5) -0.0052(6) 0.0021(6) Si1 0.0307(2) 0.0299(2) 0.0213(2) -0.00067(17) -0.00138(15) 0.00650(18) 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 O1 1.430(2) . ? C1 C2 1.522(2) . ? C2 C17 1.536(2) . ? C2 C3 1.5436(18) . ? C3 C8 1.5288(19) . ? C3 C13 1.5407(19) . ? C3 C4 1.5687(18) . ? C4 C5 1.5591(18) . ? C4 Si1 1.8765(15) . ? C5 C12 1.5417(19) . ? C5 C6 1.553(2) . ? C6 C18 1.529(2) . ? C6 C14 1.5479(19) . ? C6 C7 1.573(2) . ? C7 C8 1.5319(19) . ? C7 C9 1.549(2) . ? C7 C19 1.564(2) . ? C8 O2 1.2110(18) . ? C9 O3 1.217(2) . ? C9 C10 1.505(2) . ? C10 C11 1.519(2) . ? C11 C12 1.522(2) . ? C13 C14 1.5409(19) . ? C15 Si1 1.8595(18) . ? C16 Si1 1.8538(16) . ? C19 C20 1.493(2) . ? C20 C21 1.287(3) . ? O1 Si1 1.6502(12) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 C1 C2 114.22(12) . . ? C1 C2 C17 108.78(12) . . ? C1 C2 C3 113.47(12) . . ? C17 C2 C3 112.49(12) . . ? C8 C3 C13 110.90(11) . . ? C8 C3 C2 112.19(11) . . ? C13 C3 C2 112.90(11) . . ? C8 C3 C4 100.04(10) . . ? C13 C3 C4 108.86(11) . . ? C2 C3 C4 111.19(11) . . ? C5 C4 C3 111.16(11) . . ? C5 C4 Si1 117.35(9) . . ? C3 C4 Si1 112.83(9) . . ? C12 C5 C6 116.99(12) . . ? C12 C5 C4 111.08(12) . . ? C6 C5 C4 110.29(11) . . ? C18 C6 C14 108.87(12) . . ? C18 C6 C5 111.60(13) . . ? C14 C6 C5 105.00(11) . . ? C18 C6 C7 112.50(12) . . ? C14 C6 C7 108.36(12) . . ? C5 C6 C7 110.18(11) . . ? C8 C7 C9 113.24(12) . . ? C8 C7 C19 107.59(12) . . ? C9 C7 C19 106.81(12) . . ? C8 C7 C6 106.59(11) . . ? C9 C7 C6 110.30(11) . . ? C19 C7 C6 112.39(12) . . ? O2 C8 C3 124.29(13) . . ? O2 C8 C7 121.66(13) . . ? C3 C8 C7 113.89(11) . . ? O3 C9 C10 116.96(14) . . ? O3 C9 C7 119.07(14) . . ? C10 C9 C7 123.94(13) . . ? C9 C10 C11 120.84(13) . . ? C10 C11 C12 114.83(14) . . ? C11 C12 C5 116.82(13) . . ? C3 C13 C14 110.84(11) . . ? C13 C14 C6 110.95(11) . . ? C20 C19 C7 114.55(13) . . ? C21 C20 C19 125.07(17) . . ? C1 O1 Si1 120.54(9) . . ? O1 Si1 C16 106.70(7) . . ? O1 Si1 C15 112.67(8) . . ? C16 Si1 C15 109.81(9) . . ? O1 Si1 C4 103.02(6) . . ? C16 Si1 C4 109.36(7) . . ? C15 Si1 C4 114.82(7) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.14 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.218 _refine_diff_density_min -0.133 _refine_diff_density_rms 0.033