Supplementary Material (ESI) for Chemical Communications This journal is © The Royal Society of Chemistry 2001 data_global _journal_coden_Cambridge 182 _publ_requested_journal 'Chemical Communications' loop_ _publ_author_name 'Blake, Alexander J.' 'Giblin, Gerard M. P.' 'Kirk, Douglas T.' 'Simpkins, Nigel S.' 'Wilson, Claire' _publ_contact_author_name 'Prof Nigel S Simpkins' _publ_contact_author_address ; Department of Chemistry University of Nottingham University Park Nottingham NG7 2RD UK ; _publ_contact_author_email 'NIGEL.SIMPKINS@NOTTINGHAM.AC.UK' _publ_section_title ; The Enantioselective Generation of Bridgehead Enolates ; data_6 # Cif for structure 6 M/S B108986M _database_code_CSD 172469 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H24 O Si2' _chemical_formula_weight 276.52 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 Pna2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' 'x+1/2, -y+1/2, z' '-x+1/2, y+1/2, z+1/2' _cell_length_a 12.4355(7) _cell_length_b 13.6661(8) _cell_length_c 9.8989(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1682.27(17) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 6322 _cell_measurement_theta_min 2.21 _cell_measurement_theta_max 28.51 _exptl_crystal_description 'irregular block' _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.51 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.092 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 600 _exptl_absorpt_coefficient_mu 0.200 _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 150(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 'Bruker SMART1000 CCD area detector' _diffrn_measurement_method omega _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% none _diffrn_reflns_number 10738 _diffrn_reflns_av_R_equivalents 0.042 _diffrn_reflns_av_sigmaI/netI 0.0201 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.21 _diffrn_reflns_theta_max 28.85 _reflns_number_total 3797 _reflns_number_gt 3510 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SHELXTL' _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^)+(0.0589P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens 'geometrically placed' _refine_ls_hydrogen_treatment 'riding model' _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 -0.04(9) _refine_ls_number_reflns 3797 _refine_ls_number_parameters 163 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0353 _refine_ls_R_factor_gt 0.0318 _refine_ls_wR_factor_ref 0.0820 _refine_ls_wR_factor_gt 0.0800 _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 Si1 Si 0.02838(3) 0.33660(3) 0.12949(5) 0.03583(11) Uani 1 1 d . . . O1 O 0.23315(9) 0.27485(9) 0.31211(13) 0.0399(3) Uani 1 1 d . . . C1 C 0.15455(11) 0.22132(10) 0.31824(15) 0.0280(3) Uani 1 1 d . . . Si2 Si 0.17490(3) 0.19574(3) 0.60613(5) 0.03352(11) Uani 1 1 d . . . C2 C 0.06576(11) 0.21962(10) 0.21530(16) 0.0283(3) Uani 1 1 d . . . C3 C 0.05400(12) 0.11890(11) 0.14119(17) 0.0338(3) Uani 1 1 d . . . H3A H 0.0149 0.1213 0.0530 0.041 Uiso 1 1 calc R . . C4 C 0.13830(12) 0.04377(11) 0.15092(18) 0.0364(3) Uani 1 1 d . . . H4A H 0.1701 0.0194 0.0704 0.044 Uiso 1 1 calc R . . C5 C 0.17118(12) 0.00906(11) 0.26907(19) 0.0390(4) Uani 1 1 d . . . H5A H 0.2255 -0.0398 0.2704 0.047 Uiso 1 1 calc R . . C6 C 0.12683(12) 0.04342(11) 0.39727(17) 0.0350(3) Uani 1 1 d . . . H6A H 0.1350 -0.0027 0.4750 0.042 Uiso 1 1 calc R . . C7 C 0.13003(11) 0.15535(10) 0.43521(15) 0.0278(3) Uani 1 1 d . . . C8 C 0.02539(11) 0.10487(10) 0.39885(16) 0.0302(3) Uani 1 1 d . . . H8A H -0.0286 0.0931 0.4719 0.036 Uiso 1 1 calc R . . C9 C -0.01349(11) 0.14366(11) 0.26451(16) 0.0307(3) Uani 1 1 d . . . H9A H -0.0921 0.1562 0.2522 0.037 Uiso 1 1 calc R . . C10 C -0.08889(18) 0.31336(18) 0.0164(2) 0.0593(6) Uani 1 1 d . . . H10A H -0.1092 0.3743 -0.0292 0.089 Uiso 1 1 calc R . . H10B H -0.1497 0.2895 0.0702 0.089 Uiso 1 1 calc R . . H10C H -0.0694 0.2641 -0.0512 0.089 Uiso 1 1 calc R . . C11 C 0.14546(18) 0.38231(15) 0.0300(2) 0.0539(5) Uani 1 1 d . . . H11A H 0.1259 0.4437 -0.0150 0.081 Uiso 1 1 calc R . . H11B H 0.1655 0.3335 -0.0380 0.081 Uiso 1 1 calc R . . H11C H 0.2064 0.3938 0.0907 0.081 Uiso 1 1 calc R . . C12 C -0.0092(2) 0.42532(14) 0.2637(2) 0.0596(5) Uani 1 1 d . . . H12A H -0.0294 0.4878 0.2222 0.089 Uiso 1 1 calc R . . H12B H 0.0521 0.4354 0.3243 0.089 Uiso 1 1 calc R . . H12C H -0.0702 0.3996 0.3153 0.089 Uiso 1 1 calc R . . C13 C 0.1153(2) 0.11487(17) 0.7377(2) 0.0628(6) Uani 1 1 d . . . H13A H 0.1392 0.1364 0.8272 0.094 Uiso 1 1 calc R . . H13B H 0.1387 0.0473 0.7224 0.094 Uiso 1 1 calc R . . H13C H 0.0367 0.1183 0.7327 0.094 Uiso 1 1 calc R . . C14 C 0.32444(14) 0.19108(16) 0.6157(3) 0.0536(4) Uani 1 1 d . . . H14A H 0.3479 0.2123 0.7056 0.080 Uiso 1 1 calc R . . H14B H 0.3552 0.2346 0.5471 0.080 Uiso 1 1 calc R . . H14C H 0.3489 0.1239 0.5996 0.080 Uiso 1 1 calc R . . C15 C 0.12711(14) 0.32400(12) 0.6285(2) 0.0466(4) Uani 1 1 d . . . H15A H 0.1492 0.3481 0.7176 0.070 Uiso 1 1 calc R . . H15B H 0.0485 0.3258 0.6216 0.070 Uiso 1 1 calc R . . H15C H 0.1585 0.3656 0.5581 0.070 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 0.0393(2) 0.0363(2) 0.0319(2) 0.00754(18) -0.00010(17) 0.00298(16) O1 0.0314(6) 0.0475(6) 0.0408(6) 0.0051(5) -0.0020(5) -0.0144(5) C1 0.0271(7) 0.0289(6) 0.0282(7) -0.0034(6) 0.0015(5) -0.0003(5) Si2 0.0335(2) 0.0404(2) 0.0267(2) -0.00127(18) -0.00229(16) -0.00479(15) C2 0.0274(7) 0.0298(7) 0.0277(7) 0.0004(5) 0.0009(5) -0.0005(5) C3 0.0337(7) 0.0366(7) 0.0313(8) -0.0048(6) -0.0030(6) -0.0012(6) C4 0.0322(7) 0.0386(7) 0.0382(9) -0.0140(7) 0.0023(6) 0.0013(6) C5 0.0349(8) 0.0328(7) 0.0493(10) -0.0096(7) -0.0035(7) 0.0074(6) C6 0.0393(8) 0.0268(6) 0.0388(9) 0.0016(6) -0.0035(7) 0.0017(6) C7 0.0275(7) 0.0279(6) 0.0279(7) -0.0016(6) -0.0004(5) -0.0015(5) C8 0.0276(7) 0.0309(7) 0.0321(8) 0.0011(6) 0.0022(5) -0.0047(5) C9 0.0244(6) 0.0328(6) 0.0350(8) 0.0007(6) -0.0013(6) -0.0017(5) C10 0.0527(12) 0.0731(13) 0.0521(13) 0.0163(10) -0.0187(9) 0.0026(10) C11 0.0587(12) 0.0560(11) 0.0470(12) 0.0210(9) 0.0067(8) -0.0061(9) C12 0.0843(15) 0.0446(10) 0.0498(13) 0.0017(9) 0.0036(10) 0.0235(10) C13 0.0829(15) 0.0738(14) 0.0317(10) 0.0075(10) 0.0016(9) -0.0265(12) C14 0.0367(8) 0.0776(11) 0.0465(11) 0.0000(11) -0.0129(8) 0.0050(8) C15 0.0451(9) 0.0460(8) 0.0487(11) -0.0192(9) -0.0031(8) -0.0042(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Si1 C12 1.858(2) . ? Si1 C11 1.865(2) . ? Si1 C10 1.866(2) . ? Si1 C2 1.8690(15) . ? O1 C1 1.2224(18) . ? C1 C7 1.499(2) . ? C1 C2 1.503(2) . ? Si2 C13 1.862(2) . ? Si2 C14 1.8631(17) . ? Si2 C15 1.8640(17) . ? Si2 C7 1.8651(16) . ? C2 C9 1.512(2) . ? C2 C3 1.567(2) . ? C3 C4 1.471(2) . ? C3 C9 1.520(2) . ? C3 H3A 1.0000 . ? C4 C5 1.327(3) . ? C4 H4A 0.9500 . ? C5 C6 1.461(2) . ? C5 H5A 0.9500 . ? C6 C8 1.515(2) . ? C6 C7 1.576(2) . ? C6 H6A 1.0000 . ? C7 C8 1.5161(19) . ? C8 C9 1.511(2) . ? C8 H8A 1.0000 . ? C9 H9A 1.0000 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 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 C12 Si1 C11 110.81(11) . . ? C12 Si1 C10 110.06(12) . . ? C11 Si1 C10 110.50(11) . . ? C12 Si1 C2 107.21(8) . . ? C11 Si1 C2 109.41(8) . . ? C10 Si1 C2 108.75(9) . . ? O1 C1 C7 124.12(14) . . ? O1 C1 C2 124.28(14) . . ? C7 C1 C2 111.41(12) . . ? C13 Si2 C14 109.96(11) . . ? C13 Si2 C15 110.37(11) . . ? C14 Si2 C15 110.14(9) . . ? C13 Si2 C7 109.86(8) . . ? C14 Si2 C7 109.56(9) . . ? C15 Si2 C7 106.90(8) . . ? C1 C2 C9 105.73(12) . . ? C1 C2 C3 113.56(12) . . ? C9 C2 C3 59.12(10) . . ? C1 C2 Si1 118.53(10) . . ? C9 C2 Si1 124.86(10) . . ? C3 C2 Si1 121.03(11) . . ? C4 C3 C9 119.78(14) . . ? C4 C3 C2 121.09(12) . . ? C9 C3 C2 58.65(9) . . ? C4 C3 H3A 115.2 . . ? C9 C3 H3A 115.2 . . ? C2 C3 H3A 115.2 . . ? C5 C4 C3 121.81(15) . . ? C5 C4 H4A 119.1 . . ? C3 C4 H4A 119.1 . . ? C4 C5 C6 122.31(13) . . ? C4 C5 H5A 118.8 . . ? C6 C5 H5A 118.8 . . ? C5 C6 C8 120.08(14) . . ? C5 C6 C7 120.63(13) . . ? C8 C6 C7 58.70(9) . . ? C5 C6 H6A 115.3 . . ? C8 C6 H6A 115.3 . . ? C7 C6 H6A 115.3 . . ? C1 C7 C8 105.36(12) . . ? C1 C7 C6 113.89(13) . . ? C8 C7 C6 58.67(9) . . ? C1 C7 Si2 117.51(10) . . ? C8 C7 Si2 127.35(11) . . ? C6 C7 Si2 120.74(11) . . ? C9 C8 C6 116.85(13) . . ? C9 C8 C7 108.90(12) . . ? C6 C8 C7 62.63(9) . . ? C9 C8 H8A 118.5 . . ? C6 C8 H8A 118.5 . . ? C7 C8 H8A 118.5 . . ? C8 C9 C2 108.41(12) . . ? C8 C9 C3 116.88(12) . . ? C2 C9 C3 62.23(10) . . ? C8 C9 H9A 118.7 . . ? C2 C9 H9A 118.7 . . ? C3 C9 H9A 118.7 . . ? Si1 C10 H10A 109.5 . . ? Si1 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? Si1 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? Si1 C11 H11A 109.5 . . ? Si1 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? Si1 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? Si1 C12 H12A 109.5 . . ? Si1 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? Si1 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? Si2 C13 H13A 109.5 . . ? Si2 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? Si2 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? Si2 C14 H14A 109.5 . . ? Si2 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? Si2 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? Si2 C15 H15A 109.5 . . ? Si2 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? Si2 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 C1 C2 C9 -179.62(14) . . . . ? C7 C1 C2 C9 -4.44(16) . . . . ? O1 C1 C2 C3 117.69(16) . . . . ? C7 C1 C2 C3 -67.13(16) . . . . ? O1 C1 C2 Si1 -33.6(2) . . . . ? C7 C1 C2 Si1 141.56(11) . . . . ? C12 Si1 C2 C1 -57.48(14) . . . . ? C11 Si1 C2 C1 62.76(14) . . . . ? C10 Si1 C2 C1 -176.46(13) . . . . ? C12 Si1 C2 C9 81.52(16) . . . . ? C11 Si1 C2 C9 -158.24(14) . . . . ? C10 Si1 C2 C9 -37.45(17) . . . . ? C12 Si1 C2 C3 153.42(14) . . . . ? C11 Si1 C2 C3 -86.34(13) . . . . ? C10 Si1 C2 C3 34.44(15) . . . . ? C1 C2 C3 C4 -13.4(2) . . . . ? C9 C2 C3 C4 -108.16(17) . . . . ? Si1 C2 C3 C4 137.16(14) . . . . ? C1 C2 C3 C9 94.81(14) . . . . ? Si1 C2 C3 C9 -114.68(12) . . . . ? C9 C3 C4 C5 -12.5(2) . . . . ? C2 C3 C4 C5 56.7(2) . . . . ? C3 C4 C5 C6 -0.5(2) . . . . ? C4 C5 C6 C8 12.7(2) . . . . ? C4 C5 C6 C7 -56.5(2) . . . . ? O1 C1 C7 C8 179.33(14) . . . . ? C2 C1 C7 C8 4.15(15) . . . . ? O1 C1 C7 C6 -118.58(16) . . . . ? C2 C1 C7 C6 66.23(16) . . . . ? O1 C1 C7 Si2 30.84(19) . . . . ? C2 C1 C7 Si2 -144.35(10) . . . . ? C5 C6 C7 C1 14.78(19) . . . . ? C8 C6 C7 C1 -93.99(14) . . . . ? C5 C6 C7 C8 108.77(16) . . . . ? C5 C6 C7 Si2 -133.56(13) . . . . ? C8 C6 C7 Si2 117.67(13) . . . . ? C13 Si2 C7 C1 169.97(13) . . . . ? C14 Si2 C7 C1 -69.13(13) . . . . ? C15 Si2 C7 C1 50.20(13) . . . . ? C13 Si2 C7 C8 29.32(16) . . . . ? C14 Si2 C7 C8 150.21(13) . . . . ? C15 Si2 C7 C8 -90.46(13) . . . . ? C13 Si2 C7 C6 -42.79(15) . . . . ? C14 Si2 C7 C6 78.10(13) . . . . ? C15 Si2 C7 C6 -162.57(12) . . . . ? C5 C6 C8 C9 -11.2(2) . . . . ? C7 C6 C8 C9 98.44(14) . . . . ? C5 C6 C8 C7 -109.69(16) . . . . ? C1 C7 C8 C9 -2.19(15) . . . . ? C6 C7 C8 C9 -111.12(14) . . . . ? Si2 C7 C8 C9 142.14(12) . . . . ? C1 C7 C8 C6 108.93(13) . . . . ? Si2 C7 C8 C6 -106.74(14) . . . . ? C6 C8 C9 C2 -68.66(16) . . . . ? C7 C8 C9 C2 -0.46(16) . . . . ? C6 C8 C9 C3 -1.11(18) . . . . ? C7 C8 C9 C3 67.09(16) . . . . ? C1 C2 C9 C8 2.91(16) . . . . ? C3 C2 C9 C8 111.30(13) . . . . ? Si1 C2 C9 C8 -140.31(12) . . . . ? C1 C2 C9 C3 -108.39(13) . . . . ? Si1 C2 C9 C3 108.39(14) . . . . ? C4 C3 C9 C8 12.71(19) . . . . ? C2 C3 C9 C8 -97.66(14) . . . . ? C4 C3 C9 C2 110.36(15) . . . . ? _diffrn_measured_fraction_theta_max 0.929 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.393 _refine_diff_density_min -0.147 _refine_diff_density_rms 0.040 ############################################################################ data_8 # cif for structure 8 M/S B108986M _database_code_CSD 172470 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C12 H16 O Si' _chemical_formula_sum 'C12 H16 O Si' _chemical_formula_weight 204.34 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 Monoclinic _symmetry_space_group_name_H-M P2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 6.1568(6) _cell_length_b 7.4191(7) _cell_length_c 12.9873(12) _cell_angle_alpha 90.00 _cell_angle_beta 101.996(2) _cell_angle_gamma 90.00 _cell_volume 580.3(2) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 4353 _cell_measurement_theta_min 3.2 _cell_measurement_theta_max 28.55 _exptl_crystal_description lath _exptl_crystal_colour colourless _exptl_crystal_size_max 0.64 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.169 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 220 _exptl_absorpt_coefficient_mu 0.169 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.709 _exptl_absorpt_correction_T_max 0.952 _exptl_absorpt_process_details 'SHELXTL version 5.1 (Bruker, 1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 'Bruker SMART CCD area detector' _diffrn_measurement_method omega _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% none _diffrn_reflns_number 2552 _diffrn_reflns_av_R_equivalents 0.023 _diffrn_reflns_av_sigmaI/netI 0.012 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 3.18 _diffrn_reflns_theta_max 28.55 _reflns_number_total 2562 _reflns_number_gt 2483 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART version 5.054 (Bruker, 1998)' _computing_cell_refinement 'Bruker SAINT version 6.02a (Bruker, 2000)' _computing_data_reduction 'Bruker SAINT; Bruker SHELXTL (Bruker, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'SHELXL-97; PLATON (Spek, 2001)' _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^)+(0.053P)^2^+0.037P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary ? _atom_sites_solution_hydrogens 'placed geometrically' _refine_ls_hydrogen_treatment 'riding model' _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(8) _refine_ls_number_reflns 2552 _refine_ls_number_parameters 127 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0276 _refine_ls_R_factor_gt 0.0266 _refine_ls_wR_factor_ref 0.0719 _refine_ls_wR_factor_gt 0.0709 _refine_ls_goodness_of_fit_ref 1.058 _refine_ls_restrained_S_all 1.058 _refine_ls_shift/su_max 0.002 _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 Si Si 0.11934(5) 0.46954(4) 0.33414(2) 0.02238(9) Uani 1 1 d . . . C1 C 0.16795(19) 0.65457(16) 0.23953(9) 0.0210(2) Uani 1 1 d . . . C2 C 0.3082(2) 0.80972(18) 0.29540(10) 0.0263(3) Uani 1 1 d . . . H2 H 0.3226 0.8174 0.3695 0.032 Uiso 1 1 calc R . . C3 C 0.4136(2) 0.93661(18) 0.24995(11) 0.0308(3) Uani 1 1 d . . . H3 H 0.4972 1.0209 0.2973 0.037 Uiso 1 1 calc R . . C4 C 0.4193(2) 0.9651(2) 0.13856(11) 0.0330(3) Uani 1 1 d . . . H4 H 0.5014 1.0675 0.1247 0.040 Uiso 1 1 calc R . . C5 C 0.3262(3) 0.8686(2) 0.05348(11) 0.0336(3) Uani 1 1 d . . . H5 H 0.3496 0.9095 -0.0127 0.040 Uiso 1 1 calc R . . C6 C 0.1863(2) 0.69915(19) 0.05342(10) 0.0309(3) Uani 1 1 d . . . H6 H 0.1746 0.6272 -0.0126 0.037 Uiso 1 1 calc R . . C7 C -0.0380(2) 0.75191(19) 0.07349(10) 0.0316(3) Uani 1 1 d . . . H7 H -0.1581 0.7937 0.0207 0.038 Uiso 1 1 calc R . . C8 C -0.0460(2) 0.73242(17) 0.17481(11) 0.0272(3) Uani 1 1 d . . . H8 H -0.1712 0.7636 0.2033 0.033 Uiso 1 1 calc R . . C9 C 0.2803(2) 0.58918(17) 0.15183(9) 0.0244(2) Uani 1 1 d . . . O1 O 0.41742(15) 0.46991(18) 0.15849(7) 0.0339(2) Uani 1 1 d . . . C10 C -0.0441(2) 0.28470(19) 0.25714(11) 0.0323(3) Uani 1 1 d . . . H10A H -0.0699 0.1889 0.3051 0.048 Uiso 1 1 calc R . . H10B H 0.0387 0.2358 0.2066 0.048 Uiso 1 1 calc R . . H10C H -0.1869 0.3322 0.2192 0.048 Uiso 1 1 calc R . . C11 C -0.0412(3) 0.5769(2) 0.42595(12) 0.0391(3) Uani 1 1 d . . . H11A H -0.0708 0.4869 0.4766 0.059 Uiso 1 1 calc R . . H11B H -0.1822 0.6235 0.3854 0.059 Uiso 1 1 calc R . . H11C H 0.0456 0.6761 0.4638 0.059 Uiso 1 1 calc R . . C12 C 0.3894(2) 0.3849(2) 0.41226(11) 0.0316(3) Uani 1 1 d . . . H12A H 0.3614 0.2901 0.4604 0.047 Uiso 1 1 calc R . . H12B H 0.4700 0.4844 0.4529 0.047 Uiso 1 1 calc R . . H12C H 0.4785 0.3359 0.3645 0.047 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 0.02382(15) 0.02182(16) 0.02152(15) 0.00067(13) 0.00474(10) -0.00031(14) C1 0.0224(5) 0.0198(6) 0.0204(5) -0.0007(4) 0.0035(4) 0.0011(4) C2 0.0287(6) 0.0255(6) 0.0240(6) -0.0044(5) 0.0036(5) 0.0005(5) C3 0.0293(6) 0.0253(7) 0.0364(7) -0.0053(5) 0.0035(5) -0.0028(5) C4 0.0307(6) 0.0264(6) 0.0435(7) 0.0078(7) 0.0114(5) -0.0022(7) C5 0.0395(7) 0.0322(7) 0.0311(6) 0.0108(6) 0.0120(5) 0.0029(6) C6 0.0444(7) 0.0266(6) 0.0210(6) 0.0025(5) 0.0053(5) 0.0006(5) C7 0.0331(6) 0.0256(6) 0.0304(7) 0.0047(5) -0.0065(5) -0.0025(5) C8 0.0229(6) 0.0232(6) 0.0339(6) 0.0024(5) 0.0021(5) 0.0010(5) C9 0.0301(6) 0.0216(6) 0.0218(6) -0.0003(4) 0.0058(4) 0.0008(5) O1 0.0415(5) 0.0304(5) 0.0330(4) 0.0021(5) 0.0148(4) 0.0103(6) C10 0.0316(6) 0.0266(7) 0.0358(7) 0.0004(5) 0.0001(5) -0.0035(5) C11 0.0479(8) 0.0353(8) 0.0416(8) -0.0022(6) 0.0262(7) -0.0009(6) C12 0.0303(6) 0.0320(7) 0.0290(6) 0.0076(5) -0.0016(5) -0.0008(6) _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 C10 1.8641(14) . ? Si C11 1.8766(14) . ? Si C12 1.8674(14) . ? Si C1 1.9070(12) . ? C1 C8 1.5217(16) . ? C1 C2 1.5287(17) . ? C1 C9 1.5293(16) . ? C2 C3 1.347(2) . ? C2 H2 0.9500 . ? C3 C4 1.4698(19) . ? C3 H3 0.9500 . ? C4 C5 1.341(2) . ? C4 H4 0.9500 . ? C5 C6 1.524(2) . ? C5 H5 0.9500 . ? C6 C7 1.509(2) . ? C6 C9 1.5252(17) . ? C6 H6 1.0000 . ? C7 C8 1.335(2) . ? C7 H7 0.9500 . ? C8 H8 0.9500 . ? C9 O1 1.2136(18) . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 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 C10 Si C11 110.86(7) . . ? C10 Si C12 111.37(7) . . ? C11 Si C12 108.94(7) . . ? C1 Si C10 108.87(6) . . ? C1 Si C11 106.13(6) . . ? C1 Si C12 110.54(6) . . ? C8 C1 C2 108.38(10) . . ? C8 C1 C9 100.53(9) . . ? C2 C1 C9 107.09(9) . . ? C8 C1 Si 113.29(8) . . ? C2 C1 Si 112.65(8) . . ? C9 C1 Si 114.04(8) . . ? C3 C2 C1 126.46(11) . . ? C3 C2 H2 116.8 . . ? C1 C2 H2 116.8 . . ? C2 C3 C4 130.10(12) . . ? C2 C3 H3 114.9 . . ? C4 C3 H3 114.9 . . ? C5 C4 C3 129.83(14) . . ? C5 C4 H4 115.1 . . ? C3 C4 H4 115.1 . . ? C4 C5 C6 125.84(12) . . ? C4 C5 H5 117.1 . . ? C6 C5 H5 117.1 . . ? C7 C6 C5 108.86(12) . . ? C7 C6 C9 101.27(11) . . ? C5 C6 C9 108.96(11) . . ? C7 C6 H6 112.4 . . ? C5 C6 H6 112.4 . . ? C9 C6 H6 112.4 . . ? C8 C7 C6 111.41(12) . . ? C8 C7 H7 124.3 . . ? C6 C7 H7 124.3 . . ? C7 C8 C1 112.35(12) . . ? C7 C8 H8 123.8 . . ? C1 C8 H8 123.8 . . ? O1 C9 C6 125.94(11) . . ? O1 C9 C1 126.43(11) . . ? C6 C9 C1 107.63(10) . . ? Si C10 H10A 109.5 . . ? Si C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? Si C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? Si C11 H11A 109.5 . . ? Si C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? Si C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? Si C12 H12A 109.5 . . ? Si C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? Si C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 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 C10 Si C1 C8 58.53(10) . . . . ? C12 Si C1 C8 -178.84(9) . . . . ? C11 Si C1 C8 -60.86(10) . . . . ? C10 Si C1 C2 -178.00(9) . . . . ? C12 Si C1 C2 -55.36(10) . . . . ? C11 Si C1 C2 62.62(10) . . . . ? C10 Si C1 C9 -55.66(10) . . . . ? C12 Si C1 C9 66.97(10) . . . . ? C11 Si C1 C9 -175.05(9) . . . . ? C8 C1 C2 C3 -70.53(16) . . . . ? C9 C1 C2 C3 37.14(17) . . . . ? Si C1 C2 C3 163.31(11) . . . . ? C1 C2 C3 C4 1.9(2) . . . . ? C2 C3 C4 C5 -2.3(3) . . . . ? C3 C4 C5 C6 0.1(2) . . . . ? C4 C5 C6 C7 73.29(18) . . . . ? C4 C5 C6 C9 -36.32(19) . . . . ? C5 C6 C7 C8 -97.02(13) . . . . ? C9 C6 C7 C8 17.70(15) . . . . ? C6 C7 C8 C1 -2.75(16) . . . . ? C2 C1 C8 C7 98.73(13) . . . . ? C9 C1 C8 C7 -13.40(14) . . . . ? Si C1 C8 C7 -135.48(10) . . . . ? C7 C6 C9 O1 153.40(14) . . . . ? C5 C6 C9 O1 -91.95(17) . . . . ? C7 C6 C9 C1 -25.75(13) . . . . ? C5 C6 C9 C1 88.89(13) . . . . ? C8 C1 C9 O1 -155.05(14) . . . . ? C2 C1 C9 O1 91.83(16) . . . . ? Si C1 C9 O1 -33.50(17) . . . . ? C8 C1 C9 C6 24.10(12) . . . . ? C2 C1 C9 C6 -89.02(12) . . . . ? Si C1 C9 C6 145.65(9) . . . . ? _diffrn_measured_fraction_theta_max 0.902 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.978 _refine_diff_density_max 0.29 _refine_diff_density_min -0.13 _refine_diff_density_rms 0.04