Supplementary Material (ESI) for Organic & Biomolecular Chemistry This journal is (c) The Royal Society of Chemistry 2007 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_Cambridge 0177 _publ_contact_author_name 'P. Steel' _publ_contact_author_address ; Chemistry Department Durham University University Science Laboratories South Road Durham Co Durham DH1 3LE UNITED KINGDOM ; _publ_contact_author_email P.G.STEEL@DURHAM.AC.UK _publ_section_title ; Hosomi-Sakurai Reactions of Silacyclohexenes ; loop_ _publ_author_name 'P. Steel' 'Nicholas J. Hughes' 'Robert D. C. Pullin' 'Mahesh J. Sanganee' 'Jonathan D. Sellars' ; M.J.Turner ; data_45 _database_code_depnum_ccdc_archive 'CCDC 298852' _audit_creation_date 05-07-27 _audit_creation_method CRYSTALS_ver_12.80 _chemical_name_systematic ; (1S*,2S*,3R*,4R*)-4-Cyclohexyl-3-ethenyl-4-methoxy-2-methyl-1-phenylbutan-1-ol ; _chemical_melting_point 380(1) _cell_length_a 16.9623(4) _cell_length_b 9.9591(2) _cell_length_c 11.0721(3) _cell_angle_alpha 90 _cell_angle_beta 96.287(1) _cell_angle_gamma 90 _cell_volume 1859.15(8) _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 1 21/c 1 ' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z -x,y+1/2,-z+1/2 x,-y+1/2,z+1/2 loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4' H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4' O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 4 _chemical_formula_sum 'C20 H30 O2' _chemical_formula_moiety 'C20 H30 O2' _chemical_compound_source ? _chemical_formula_weight 302.46 _cell_measurement_reflns_used 7953 _cell_measurement_theta_min 2 _cell_measurement_theta_max 30 _cell_measurement_temperature 120 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_min 0.12 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_max 0.36 _exptl_crystal_density_diffrn 1.081 _exptl_crystal_density_meas ? _exptl_crystal_F_000 664 _exptl_absorpt_coefficient_mu 0.067 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS (Siemens, 1996)' _exptl_absorpt_correction_T_min 0.89 _exptl_absorpt_correction_T_max 0.99 _diffrn_measurement_device_type 'Siemens SMART 1K CCD area detector' _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_method \w-scans _computing_data_collection 'SMART version 5.054 (Bruker, 1999)' _computing_cell_refinement 'SAINT version 6.45A (Bruker, 2003)' _computing_data_reduction 'SAINT version 6.45A (Bruker, 2003)' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_publication_material 'CRYSTALS (Betteridge et al., 2003)' _computing_molecular_graphics 'CAMERON (Watkin et al., 1996)' _diffrn_ambient_temperature 120 _diffrn_reflns_number 23555 _reflns_number_total 5273 _diffrn_reflns_av_R_equivalents 0.023 _diffrn_reflns_theta_min 1.208 _diffrn_reflns_theta_max 30.526 _diffrn_measured_fraction_theta_max 0.926 _diffrn_reflns_theta_full 28.695 _diffrn_measured_fraction_theta_full 0.997 _diffrn_reflns_limit_h_min -24 _diffrn_reflns_limit_h_max 23 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 14 _reflns_limit_h_min -24 _reflns_limit_h_max 23 _reflns_limit_k_min 0 _reflns_limit_k_max 13 _reflns_limit_l_min 0 _reflns_limit_l_max 15 _oxford_diffrn_Wilson_B_factor 1.89 _oxford_diffrn_Wilson_scale 38.07 _atom_sites_solution_primary direct # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.18 _refine_diff_density_max 0.24 _refine_ls_number_reflns 2621 _refine_ls_number_restraints 0 _refine_ls_number_parameters 199 #_refine_ls_R_factor_ref 0.0385 _refine_ls_wR_factor_ref 0.0891 _refine_ls_goodness_of_fit_ref 1.0325 #_reflns_number_all 5260 _refine_ls_R_factor_all 0.0781 _refine_ls_wR_factor_all 0.1426 # The I/u(I) cutoff below was used for refinement as # well as the _gt R-factors: _reflns_threshold_expression I>1.90\s(I) _reflns_number_gt 2621 _refine_ls_R_factor_gt 0.0385 _refine_ls_wR_factor_gt 0.0891 _refine_ls_shift/su_max 0.000293 _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_hydrogen_treatment constr _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; w=1/[\s^2^(F^2^) + 0.05 + 0.05P] where P=(max(Fo^2^,0) + 2Fc^2^)/3 ; 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_occupancy _atom_site_adp_type _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_attached_hydrogens C1 C 0.21878(9) 0.76506(16) -0.03597(13) 0.0215 1.0000 Uani . . . . . . C2 C 0.24254(9) 0.61995(15) 0.00088(13) 0.0216 1.0000 Uani . . . . . . C3 C 0.17396(9) 0.51885(16) -0.01854(13) 0.0246 1.0000 Uani . . . . . . C4 C 0.19925(11) 0.37841(17) 0.02823(15) 0.0318 1.0000 Uani . . . . . . C5 C 0.13066(12) 0.27764(19) 0.01093(16) 0.0390 1.0000 Uani . . . . . . C6 C 0.09726(12) 0.26971(19) -0.12266(17) 0.0414 1.0000 Uani . . . . . . C7 C 0.07009(11) 0.40755(19) -0.16945(17) 0.0397 1.0000 Uani . . . . . . C8 C 0.13707(10) 0.51098(18) -0.15182(14) 0.0301 1.0000 Uani . . . . . . O9 O 0.30536(6) 0.58059(11) -0.07068(9) 0.0239 1.0000 Uani . . . . . . C10 C 0.37770(10) 0.53830(19) -0.00264(16) 0.0347 1.0000 Uani . . . . . . C11 C 0.28725(9) 0.86895(16) -0.01181(13) 0.0211 1.0000 Uani . . . . . . C12 C 0.29619(9) 0.92384(16) 0.11858(13) 0.0214 1.0000 Uani . . . . . . C13 C 0.36390(9) 1.02300(16) 0.14615(13) 0.0220 1.0000 Uani . . . . . . C14 C 0.44150(9) 0.98893(17) 0.12799(14) 0.0261 1.0000 Uani . . . . . . C15 C 0.50334(10) 1.07785(18) 0.15801(14) 0.0304 1.0000 Uani . . . . . . C16 C 0.48881(11) 1.20327(18) 0.20539(15) 0.0342 1.0000 Uani . . . . . . C17 C 0.41201(12) 1.23823(18) 0.22382(16) 0.0362 1.0000 Uani . . . . . . C18 C 0.35031(10) 1.14891(17) 0.19444(15) 0.0292 1.0000 Uani . . . . . . O19 O 0.30681(6) 0.81152(11) 0.20027(9) 0.0268 1.0000 Uani . . . . . . C20 C 0.27402(10) 0.98547(17) -0.10255(14) 0.0285 1.0000 Uani . . . . . . C21 C 0.14574(9) 0.80874(17) 0.02066(15) 0.0279 1.0000 Uani . . . . . . C22 C 0.08314(11) 0.86507(19) -0.0402(2) 0.0443 1.0000 Uani . . . . . . H11 H 0.2044 0.7627 -0.1267 0.0326 1.0000 Uiso R . . . . . H21 H 0.2649 0.6194 0.0892 0.0310 1.0000 Uiso R . . . . . H31 H 0.1308 0.5498 0.0270 0.0391 1.0000 Uiso R . . . . . H41 H 0.2428 0.3469 -0.0193 0.0464 1.0000 Uiso R . . . . . H42 H 0.2204 0.3850 0.1168 0.0465 1.0000 Uiso R . . . . . H51 H 0.1512 0.1881 0.0371 0.0603 1.0000 Uiso R . . . . . H52 H 0.0880 0.3062 0.0600 0.0592 1.0000 Uiso R . . . . . H61 H 0.1407 0.2378 -0.1700 0.0610 1.0000 Uiso R . . . . . H62 H 0.0518 0.2053 -0.1335 0.0607 1.0000 Uiso R . . . . . H71 H 0.0499 0.4019 -0.2565 0.0585 1.0000 Uiso R . . . . . H72 H 0.0249 0.4391 -0.1244 0.0588 1.0000 Uiso R . . . . . H81 H 0.1810 0.4849 -0.2006 0.0465 1.0000 Uiso R . . . . . H82 H 0.1155 0.6005 -0.1777 0.0465 1.0000 Uiso R . . . . . H101 H 0.4166 0.5215 -0.0596 0.0635 1.0000 Uiso R . . . . . H102 H 0.3682 0.4568 0.0438 0.0641 1.0000 Uiso R . . . . . H103 H 0.3964 0.6103 0.0531 0.0643 1.0000 Uiso R . . . . . H111 H 0.3380 0.8232 -0.0257 0.0317 1.0000 Uiso R . . . . . H121 H 0.2449 0.9702 0.1339 0.0319 1.0000 Uiso R . . . . . H141 H 0.4525 0.9030 0.0963 0.0394 1.0000 Uiso R . . . . . H151 H 0.5572 1.0528 0.1447 0.0457 1.0000 Uiso R . . . . . H161 H 0.5313 1.2646 0.2252 0.0531 1.0000 Uiso R . . . . . H171 H 0.4003 1.3246 0.2557 0.0536 1.0000 Uiso R . . . . . H181 H 0.2966 1.1737 0.2060 0.0451 1.0000 Uiso R . . . . . H201 H 0.3167 1.0535 -0.0846 0.0516 1.0000 Uiso R . . . . . H202 H 0.2744 0.9513 -0.1859 0.0515 1.0000 Uiso R . . . . . H203 H 0.2224 1.0265 -0.0946 0.0514 1.0000 Uiso R . . . . . H211 H 0.1465 0.7944 0.1079 0.0441 1.0000 Uiso R . . . . . H221 H 0.0826 0.8803 -0.1272 0.0678 1.0000 Uiso R . . . . . H222 H 0.0388 0.8885 0.0009 0.0669 1.0000 Uiso R . . . . . H25 H 0.3077 0.8362 0.2738 0.0524 1.0000 Uiso 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 0.0221(8) 0.0244(8) 0.0179(7) 0.0002(7) 0.0021(6) 0.0017(7) C2 0.0240(8) 0.0248(8) 0.0164(7) 0.0001(7) 0.0039(6) 0.0016(7) C3 0.0266(9) 0.0255(9) 0.0226(8) -0.0005(7) 0.0065(6) -0.0017(7) C4 0.0428(10) 0.0258(9) 0.0268(8) 0.0013(8) 0.0039(7) -0.0049(8) C5 0.0509(12) 0.0288(10) 0.0391(10) -0.0012(8) 0.0125(9) -0.0084(9) C6 0.0449(12) 0.0351(11) 0.0444(11) -0.0071(9) 0.0064(9) -0.0150(9) C7 0.0357(11) 0.0447(12) 0.0378(10) -0.0066(9) 0.0009(8) -0.0116(9) C8 0.0288(9) 0.0338(10) 0.0273(8) -0.0008(8) 0.0007(7) -0.0043(8) O9 0.0231(6) 0.0271(6) 0.0213(5) 0.0006(5) 0.0018(4) 0.0050(5) C10 0.0296(10) 0.0381(11) 0.0349(9) 0.0043(8) -0.0031(7) 0.0065(8) C11 0.0219(8) 0.0218(8) 0.0201(7) 0.0016(7) 0.0047(6) 0.0010(7) C12 0.0234(8) 0.0210(8) 0.0204(7) 0.0025(7) 0.0050(6) 0.0011(7) C13 0.0265(9) 0.0228(8) 0.0166(7) 0.0025(7) 0.0025(6) 0.0004(7) C14 0.0293(9) 0.0244(9) 0.0245(8) 0.0009(7) 0.0030(7) 0.0019(7) C15 0.0271(9) 0.0363(10) 0.0281(8) 0.0021(8) 0.0036(7) -0.0024(8) C16 0.0376(11) 0.0318(10) 0.0330(9) -0.0012(8) 0.0031(8) -0.0122(8) C17 0.0475(12) 0.0235(9) 0.0381(10) -0.0052(8) 0.0075(9) -0.0043(9) C18 0.0315(9) 0.0259(9) 0.0307(9) -0.0010(7) 0.0064(7) 0.0023(8) O19 0.0387(7) 0.0249(6) 0.0171(5) 0.0027(5) 0.0041(5) -0.0037(5) C20 0.0345(9) 0.0280(9) 0.0231(8) 0.0047(7) 0.0034(7) 0.0006(8) C21 0.0250(9) 0.0247(9) 0.0351(9) -0.0030(8) 0.0077(7) -0.0022(8) C22 0.0295(10) 0.0416(12) 0.0624(13) 0.0012(10) 0.0081(9) 0.0044(9) _refine_ls_extinction_method None _oxford_refine_ls_scale 0.14056(7) loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag C1 . C2 . 1.543(2) yes C1 . C11 . 1.557(2) yes C1 . C21 . 1.512(2) yes C1 . H11 . 1.008 no C2 . C3 . 1.536(2) yes C2 . O9 . 1.4496(17) yes C2 . H21 . 1.009 no C3 . C4 . 1.536(2) yes C3 . C8 . 1.541(2) yes C3 . H31 . 0.983 no C4 . C5 . 1.533(2) yes C4 . H41 . 1.003 no C4 . H42 . 1.009 no C5 . C6 . 1.527(3) yes C5 . H51 . 0.989 no C5 . H52 . 0.993 no C6 . C7 . 1.521(3) yes C6 . H61 . 1.001 no C6 . H62 . 1.001 no C7 . C8 . 1.530(2) yes C7 . H71 . 0.988 no C7 . H72 . 1.009 no C8 . H81 . 1.001 no C8 . H82 . 0.994 no O9 . C10 . 1.4312(19) yes C10 . H101 . 0.976 no C10 . H102 . 0.984 no C10 . H103 . 0.976 no C11 . C12 . 1.536(2) yes C11 . C20 . 1.535(2) yes C11 . H111 . 1.001 no C12 . C13 . 1.520(2) yes C12 . O19 . 1.4374(18) yes C12 . H121 . 1.015 no C13 . C14 . 1.395(2) yes C13 . C18 . 1.392(2) yes C14 . C15 . 1.385(2) yes C14 . H141 . 0.951 no C15 . C16 . 1.387(2) yes C15 . H151 . 0.973 no C16 . C17 . 1.385(3) yes C16 . H161 . 0.952 no C17 . C18 . 1.385(2) yes C17 . H171 . 0.958 no C18 . H181 . 0.966 no O19 . H25 . 0.849 no C20 . H201 . 0.995 no C20 . H202 . 0.985 no C20 . H203 . 0.979 no C21 . C22 . 1.319(2) yes C21 . H211 . 0.976 no C22 . H221 . 0.974 no C22 . H222 . 0.950 no loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C2 . C1 . C11 . 114.12(12) yes C2 . C1 . C21 . 111.21(13) yes C11 . C1 . C21 . 111.54(13) yes C2 . C1 . H11 . 105.6 no C11 . C1 . H11 . 106.3 no C21 . C1 . H11 . 107.5 no C1 . C2 . C3 . 113.89(13) yes C1 . C2 . O9 . 107.16(11) yes C3 . C2 . O9 . 109.70(12) yes C1 . C2 . H21 . 108.7 no C3 . C2 . H21 . 109.3 no O9 . C2 . H21 . 107.9 no C2 . C3 . C4 . 111.74(13) yes C2 . C3 . C8 . 112.93(12) yes C4 . C3 . C8 . 110.22(13) yes C2 . C3 . H31 . 108.5 no C4 . C3 . H31 . 108.0 no C8 . C3 . H31 . 105.1 no C3 . C4 . C5 . 111.96(15) yes C3 . C4 . H41 . 107.6 no C5 . C4 . H41 . 108.8 no C3 . C4 . H42 . 108.9 no C5 . C4 . H42 . 110.4 no H41 . C4 . H42 . 109.0 no C4 . C5 . C6 . 110.55(14) yes C4 . C5 . H51 . 108.4 no C6 . C5 . H51 . 108.6 no C4 . C5 . H52 . 109.4 no C6 . C5 . H52 . 109.3 no H51 . C5 . H52 . 110.6 no C5 . C6 . C7 . 110.47(15) yes C5 . C6 . H61 . 107.9 no C7 . C6 . H61 . 108.7 no C5 . C6 . H62 . 110.4 no C7 . C6 . H62 . 109.7 no H61 . C6 . H62 . 109.6 no C6 . C7 . C8 . 111.78(15) yes C6 . C7 . H71 . 109.9 no C8 . C7 . H71 . 109.6 no C6 . C7 . H72 . 109.3 no C8 . C7 . H72 . 108.7 no H71 . C7 . H72 . 107.4 no C3 . C8 . C7 . 112.00(13) yes C3 . C8 . H81 . 106.4 no C7 . C8 . H81 . 110.0 no C3 . C8 . H82 . 109.2 no C7 . C8 . H82 . 108.8 no H81 . C8 . H82 . 110.4 no C2 . O9 . C10 . 115.53(11) yes O9 . C10 . H101 . 108.2 no O9 . C10 . H102 . 109.8 no H101 . C10 . H102 . 110.9 no O9 . C10 . H103 . 108.5 no H101 . C10 . H103 . 109.8 no H102 . C10 . H103 . 109.6 no C1 . C11 . C12 . 113.16(12) yes C1 . C11 . C20 . 109.70(12) yes C12 . C11 . C20 . 109.78(13) yes C1 . C11 . H111 . 108.0 no C12 . C11 . H111 . 107.9 no C20 . C11 . H111 . 108.1 no C11 . C12 . C13 . 114.50(12) yes C11 . C12 . O19 . 107.89(12) yes C13 . C12 . O19 . 109.84(12) yes C11 . C12 . H121 . 108.7 no C13 . C12 . H121 . 108.2 no O19 . C12 . H121 . 107.4 no C12 . C13 . C14 . 121.14(14) yes C12 . C13 . C18 . 120.60(14) yes C14 . C13 . C18 . 118.22(15) yes C13 . C14 . C15 . 120.77(15) yes C13 . C14 . H141 . 119.9 no C15 . C14 . H141 . 119.3 no C14 . C15 . C16 . 120.35(16) yes C14 . C15 . H151 . 119.9 no C16 . C15 . H151 . 119.8 no C15 . C16 . C17 . 119.40(16) yes C15 . C16 . H161 . 120.2 no C17 . C16 . H161 . 120.4 no C16 . C17 . C18 . 120.19(16) yes C16 . C17 . H171 . 121.0 no C18 . C17 . H171 . 118.8 no C13 . C18 . C17 . 121.07(16) yes C13 . C18 . H181 . 118.6 no C17 . C18 . H181 . 120.3 no C12 . O19 . H25 . 111.5 no C11 . C20 . H201 . 109.5 no C11 . C20 . H202 . 109.7 no H201 . C20 . H202 . 110.1 no C11 . C20 . H203 . 108.9 no H201 . C20 . H203 . 109.6 no H202 . C20 . H203 . 109.1 no C1 . C21 . C22 . 124.12(17) yes C1 . C21 . H211 . 116.5 no C22 . C21 . H211 . 119.3 no C21 . C22 . H221 . 119.4 no C21 . C22 . H222 . 119.7 no H221 . C22 . H222 . 120.8 no #======================================END _chemical_name_common ;(1S*,2S*,3R*,4R*)-4-Cyclohexyl-3-ethenyl-4-methoxy-2-methyl-1- phenylbutan-1-ol ;