# Supplementary Material (ESI) for Chemical Communications
# This journal is (c) The Royal Society of Chemistry 2006


data_global
_journal_name_full               Chem.Commun.
_journal_coden_cambridge         0182

_publ_contact_author_name        'P. Steel'
_publ_contact_author_address     
;
Chemistry Department
Durham University
University Science Laboratories
South Road
Durham
Durham
DH1 3LE
UNITED KINGDOM
;

_publ_contact_author_phone       '+44 191 3744704'
_publ_contact_author_fax         '+44 191 3844737'
_publ_contact_author_email       P.G.STEEL@DURHAM.AC.UK
_publ_author_address             
;
Department of Chemistry
Durham University
Durham DH1 3LE
UK
;
_publ_section_title              
;
Hosomi-Sakurai Reactions of Silacyclic Allyl Silanes
;
_publ_section_abstract           
;
;
_publ_section_references         
;
;
_publ_section_comment            
;
;
loop_
_publ_author_name
'Jonathan D. Sellars'
'Patrick G. Steel'
'Michael J. Turner'

#=============================================
data_04srv381
_database_code_depnum_ccdc_archive 'CCDC 298851'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ' C17 H26 O2, C6 H6 O'
_chemical_formula_sum            'C23 H32 O3'
_chemical_formula_weight         356.49

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'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   P-1
_symmetry_space_group_name_Hall  '-P 1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.2609(3)
_cell_length_b                   10.8798(4)
_cell_length_c                   11.7925(5)
_cell_angle_alpha                79.854(2)
_cell_angle_beta                 79.837(2)
_cell_angle_gamma                89.219(2)
_cell_volume                     1026.76(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_exptl_crystal_density_meas      .
_exptl_crystal_density_diffrn    1.153
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             388
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.98
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_process_details   'SADABS v2.10 - G.M. Sheldrick'

_exptl_special_details           
;
The data collection nominally covered full sphere
of reciprocal Space, by a combination of 4 sets of \w scans
each set at different \f and/or 2\q angles and each
scan (10s exposure) covering 0.3\% in \w. Crystal to
detector distance 4.54 cm.
;

_diffrn_ambient_temperature      120(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 1K CCD area detector'
_diffrn_measurement_method       \w-scans
_diffrn_detector_area_resol_mean 8
_diffrn_standards_number         .
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  .
_diffrn_standards_decay_%        .
_diffrn_reflns_number            7400
_diffrn_reflns_av_R_equivalents  0.0271
_diffrn_reflns_av_sigmaI/netI    0.0569
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.78
_diffrn_reflns_theta_max         27.43
_reflns_number_total             4610
_reflns_number_gt                3178
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SMART (Bruker, 2001)'
_computing_cell_refinement       'SAINT (Bruker, 2001)'
_computing_data_reduction        'SAINT (Bruker, 2001)'
_computing_structure_solution    'SHELXTL (Bruker, 2001)'
_computing_structure_refinement  'SHELXTL (Bruker, 2001)'
_computing_molecular_graphics    'SHELXTL (Bruker, 2001)'
_computing_publication_material  'SHELXTL (Bruker, 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^)+(0.0451P)^2^+0.3545P] 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         4610
_refine_ls_number_parameters     235
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0849
_refine_ls_R_factor_gt           0.0511
_refine_ls_wR_factor_ref         0.1227
_refine_ls_wR_factor_gt          0.1089
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_restrained_S_all      1.017
_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 0.23328(14) 0.71408(12) 0.72434(10) 0.0257(3) Uani 1 1 d . . .
H1A H 0.1523 0.6646 0.7376 0.039 Uiso 1 1 calc R . .
O2 O 0.64679(14) 0.62763(11) 0.88981(10) 0.0216(3) Uani 1 1 d . . .
C12 C 0.50084(19) 0.75222(15) 0.60310(14) 0.0184(4) Uani 1 1 d . . .
H12A H 0.5046 0.8401 0.6171 0.022 Uiso 1 1 calc R . .
C9 C 0.5842(2) 0.66772(15) 0.69698(14) 0.0186(4) Uani 1 1 d . . .
H9A H 0.7055 0.6766 0.6684 0.022 Uiso 1 1 calc R . .
C14 C 0.32003(19) 0.71684(16) 0.60690(14) 0.0192(4) Uani 1 1 d . . .
H14A H 0.3167 0.6305 0.5889 0.023 Uiso 1 1 calc R . .
C7 C 0.5510(2) 0.70937(16) 0.81739(14) 0.0196(4) Uani 1 1 d . . .
H7A H 0.4315 0.6971 0.8518 0.024 Uiso 1 1 calc R . .
C15 C 0.2359(2) 0.80378(17) 0.51879(16) 0.0244(4) Uani 1 1 d . . .
H15A H 0.3033 0.8042 0.4395 0.029 Uiso 1 1 calc R . .
C2 C 0.6014(2) 0.84421(16) 0.81274(14) 0.0206(4) Uani 1 1 d . . .
C10 C 0.5413(2) 0.53149(16) 0.70806(15) 0.0243(4) Uani 1 1 d . . .
H10A H 0.4317 0.5050 0.7422 0.029 Uiso 1 1 calc R . .
C3 C 0.7675(2) 0.87924(17) 0.79003(16) 0.0257(4) Uani 1 1 d . . .
H3A H 0.8489 0.8190 0.7744 0.031 Uiso 1 1 calc R . .
C13 C 0.6015(2) 0.74779(18) 0.48158(15) 0.0250(4) Uani 1 1 d . . .
H13A H 0.5503 0.8006 0.4219 0.037 Uiso 1 1 calc R . .
H13B H 0.6048 0.6616 0.4676 0.037 Uiso 1 1 calc R . .
H13C H 0.7137 0.7784 0.4776 0.037 Uiso 1 1 calc R . .
C8 C 0.6055(2) 0.63863(17) 1.01079(15) 0.0265(4) Uani 1 1 d . . .
H8A H 0.6730 0.5818 1.0562 0.040 Uiso 1 1 calc R . .
H8B H 0.4889 0.6169 1.0395 0.040 Uiso 1 1 calc R . .
H8C H 0.6261 0.7247 1.0194 0.040 Uiso 1 1 calc R . .
C16 C 0.0640(2) 0.75450(19) 0.51647(17) 0.0306(4) Uani 1 1 d . . .
H16A H 0.0133 0.8118 0.4595 0.046 Uiso 1 1 calc R . .
H16B H -0.0040 0.7484 0.5943 0.046 Uiso 1 1 calc R . .
H16C H 0.0727 0.6718 0.4941 0.046 Uiso 1 1 calc R . .
C17 C 0.2288(2) 0.93831(19) 0.5394(2) 0.0381(5) Uani 1 1 d . . .
H17A H 0.1740 0.9895 0.4808 0.057 Uiso 1 1 calc R . .
H17B H 0.3408 0.9708 0.5328 0.057 Uiso 1 1 calc R . .
H17C H 0.1670 0.9411 0.6179 0.057 Uiso 1 1 calc R . .
C4 C 0.8151(3) 1.00101(18) 0.78999(17) 0.0315(4) Uani 1 1 d . . .
H4A H 0.9286 1.0234 0.7743 0.038 Uiso 1 1 calc R . .
C5 C 0.6987(3) 1.08975(18) 0.81253(18) 0.0358(5) Uani 1 1 d . . .
H5A H 0.7316 1.1728 0.8135 0.043 Uiso 1 1 calc R . .
C1 C 0.4852(2) 0.93482(18) 0.83360(17) 0.0311(4) Uani 1 1 d . . .
H1B H 0.3714 0.9135 0.8479 0.037 Uiso 1 1 calc R . .
C6 C 0.5345(3) 1.05695(19) 0.83361(19) 0.0374(5) Uani 1 1 d . . .
H6A H 0.4539 1.1180 0.8483 0.045 Uiso 1 1 calc R . .
C11 C 0.6444(3) 0.44640(19) 0.67399(18) 0.0374(5) Uani 1 1 d . . .
H11A H 0.7550 0.4693 0.6395 0.045 Uiso 1 1 calc R . .
H11B H 0.6081 0.3621 0.6839 0.045 Uiso 1 1 calc R . .
O10 O -0.05363(15) 0.54938(12) 0.79326(11) 0.0277(3) Uani 1 1 d . . .
H10B H -0.1472 0.5673 0.8266 0.042 Uiso 1 1 calc R . .
C30 C -0.0187(2) 0.42822(17) 0.83723(16) 0.0230(4) Uani 1 1 d . . .
C31 C -0.0818(2) 0.37058(17) 0.95133(16) 0.0251(4) Uani 1 1 d . . .
H31A H -0.1551 0.4140 1.0014 0.030 Uiso 1 1 calc R . .
C43 C 0.0873(2) 0.36336(18) 0.76427(16) 0.0265(4) Uani 1 1 d . . .
H43A H 0.1305 0.4021 0.6863 0.032 Uiso 1 1 calc R . .
C41 C 0.0687(2) 0.18490(18) 0.91941(17) 0.0288(4) Uani 1 1 d . . .
H41A H 0.0992 0.1021 0.9475 0.035 Uiso 1 1 calc R . .
C42 C 0.1298(2) 0.24252(18) 0.80535(17) 0.0291(4) Uani 1 1 d . . .
H42A H 0.2015 0.1984 0.7550 0.035 Uiso 1 1 calc R . .
C40 C -0.0372(2) 0.24954(18) 0.99165(16) 0.0273(4) Uani 1 1 d . . .
H40A H -0.0798 0.2106 1.0697 0.033 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
O1 0.0194(6) 0.0365(7) 0.0202(7) -0.0052(5) 0.0000(5) -0.0068(5)
O2 0.0265(6) 0.0222(6) 0.0173(6) -0.0040(5) -0.0070(5) 0.0018(5)
C12 0.0192(8) 0.0183(8) 0.0183(9) -0.0045(7) -0.0040(7) -0.0009(7)
C9 0.0175(8) 0.0230(9) 0.0170(9) -0.0065(7) -0.0042(7) 0.0003(7)
C14 0.0171(8) 0.0228(9) 0.0178(9) -0.0056(7) -0.0012(7) -0.0024(7)
C7 0.0198(8) 0.0223(9) 0.0182(9) -0.0054(7) -0.0053(7) 0.0013(7)
C15 0.0184(8) 0.0316(10) 0.0223(9) -0.0028(8) -0.0032(7) 0.0025(7)
C2 0.0266(9) 0.0212(9) 0.0160(9) -0.0055(7) -0.0072(7) 0.0007(7)
C10 0.0312(9) 0.0229(9) 0.0218(9) -0.0048(7) -0.0119(8) -0.0006(7)
C3 0.0282(9) 0.0241(9) 0.0259(10) -0.0065(8) -0.0052(8) -0.0012(7)
C13 0.0182(8) 0.0364(11) 0.0200(9) -0.0049(8) -0.0026(7) -0.0019(8)
C8 0.0326(10) 0.0286(10) 0.0189(9) -0.0042(8) -0.0055(8) -0.0033(8)
C16 0.0217(9) 0.0426(12) 0.0294(11) -0.0065(9) -0.0094(8) 0.0015(8)
C17 0.0305(10) 0.0290(11) 0.0547(14) -0.0014(10) -0.0135(10) 0.0057(9)
C4 0.0368(11) 0.0282(10) 0.0306(11) -0.0051(8) -0.0079(9) -0.0085(8)
C5 0.0590(14) 0.0201(10) 0.0344(11) -0.0061(8) -0.0233(10) -0.0033(9)
C1 0.0294(10) 0.0325(11) 0.0363(11) -0.0141(9) -0.0120(8) 0.0065(8)
C6 0.0485(12) 0.0278(10) 0.0451(13) -0.0172(9) -0.0231(10) 0.0155(9)
C11 0.0515(13) 0.0282(11) 0.0416(12) -0.0171(9) -0.0231(10) 0.0095(9)
O10 0.0220(6) 0.0304(7) 0.0284(7) -0.0012(6) -0.0019(5) -0.0004(5)
C30 0.0186(8) 0.0257(9) 0.0258(10) -0.0044(8) -0.0069(7) -0.0037(7)
C31 0.0203(8) 0.0311(10) 0.0248(10) -0.0083(8) -0.0023(7) -0.0018(7)
C43 0.0238(9) 0.0350(11) 0.0205(9) -0.0043(8) -0.0033(7) -0.0034(8)
C41 0.0265(9) 0.0269(10) 0.0354(11) -0.0060(8) -0.0114(8) -0.0016(8)
C42 0.0262(9) 0.0361(11) 0.0279(10) -0.0137(9) -0.0048(8) 0.0022(8)
C40 0.0270(9) 0.0308(10) 0.0231(10) -0.0021(8) -0.0037(8) -0.0058(8)

_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 C14 1.438(2) . ?
O1 H1A 0.8400 . ?
O2 C8 1.433(2) . ?
O2 C7 1.448(2) . ?
C12 C13 1.533(2) . ?
C12 C14 1.539(2) . ?
C12 C9 1.561(2) . ?
C12 H12A 1.0000 . ?
C9 C10 1.506(2) . ?
C9 C7 1.544(2) . ?
C9 H9A 1.0000 . ?
C14 C15 1.532(2) . ?
C14 H14A 1.0000 . ?
C7 C2 1.519(2) . ?
C7 H7A 1.0000 . ?
C15 C17 1.524(3) . ?
C15 C16 1.531(2) . ?
C15 H15A 1.0000 . ?
C2 C1 1.389(2) . ?
C2 C3 1.396(2) . ?
C10 C11 1.316(3) . ?
C10 H10A 0.9500 . ?
C3 C4 1.387(2) . ?
C3 H3A 0.9500 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C4 C5 1.379(3) . ?
C4 H4A 0.9500 . ?
C5 C6 1.375(3) . ?
C5 H5A 0.9500 . ?
C1 C6 1.395(3) . ?
C1 H1B 0.9500 . ?
C6 H6A 0.9500 . ?
C11 H11A 0.9500 . ?
C11 H11B 0.9500 . ?
O10 C30 1.375(2) . ?
O10 H10B 0.8400 . ?
C30 C43 1.392(2) . ?
C30 C31 1.393(2) . ?
C31 C40 1.387(3) . ?
C31 H31A 0.9500 . ?
C43 C42 1.382(3) . ?
C43 H43A 0.9500 . ?
C41 C40 1.385(3) . ?
C41 C42 1.389(3) . ?
C41 H41A 0.9500 . ?
C42 H42A 0.9500 . ?
C40 H40A 0.9500 . ?

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
C14 O1 H1A 109.5 . . ?
C8 O2 C7 112.36(13) . . ?
C13 C12 C14 110.08(13) . . ?
C13 C12 C9 108.76(13) . . ?
C14 C12 C9 114.03(13) . . ?
C13 C12 H12A 107.9 . . ?
C14 C12 H12A 107.9 . . ?
C9 C12 H12A 107.9 . . ?
C10 C9 C7 111.21(14) . . ?
C10 C9 C12 112.25(13) . . ?
C7 C9 C12 113.27(13) . . ?
C10 C9 H9A 106.5 . . ?
C7 C9 H9A 106.5 . . ?
C12 C9 H9A 106.5 . . ?
O1 C14 C15 110.75(13) . . ?
O1 C14 C12 108.00(12) . . ?
C15 C14 C12 113.98(14) . . ?
O1 C14 H14A 108.0 . . ?
C15 C14 H14A 108.0 . . ?
C12 C14 H14A 108.0 . . ?
O2 C7 C2 109.30(13) . . ?
O2 C7 C9 105.68(12) . . ?
C2 C7 C9 113.62(14) . . ?
O2 C7 H7A 109.4 . . ?
C2 C7 H7A 109.4 . . ?
C9 C7 H7A 109.4 . . ?
C17 C15 C16 110.74(15) . . ?
C17 C15 C14 112.97(15) . . ?
C16 C15 C14 111.30(15) . . ?
C17 C15 H15A 107.2 . . ?
C16 C15 H15A 107.2 . . ?
C14 C15 H15A 107.2 . . ?
C1 C2 C3 118.29(16) . . ?
C1 C2 C7 121.44(16) . . ?
C3 C2 C7 120.25(15) . . ?
C11 C10 C9 124.87(18) . . ?
C11 C10 H10A 117.6 . . ?
C9 C10 H10A 117.6 . . ?
C4 C3 C2 120.76(18) . . ?
C4 C3 H3A 119.6 . . ?
C2 C3 H3A 119.6 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O2 C8 H8A 109.5 . . ?
O2 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
O2 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C15 C17 H17A 109.5 . . ?
C15 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C15 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C5 C4 C3 120.44(19) . . ?
C5 C4 H4A 119.8 . . ?
C3 C4 H4A 119.8 . . ?
C6 C5 C4 119.44(18) . . ?
C6 C5 H5A 120.3 . . ?
C4 C5 H5A 120.3 . . ?
C2 C1 C6 120.44(18) . . ?
C2 C1 H1B 119.8 . . ?
C6 C1 H1B 119.8 . . ?
C5 C6 C1 120.62(18) . . ?
C5 C6 H6A 119.7 . . ?
C1 C6 H6A 119.7 . . ?
C10 C11 H11A 120.0 . . ?
C10 C11 H11B 120.0 . . ?
H11A C11 H11B 120.0 . . ?
C30 O10 H10B 109.5 . . ?
O10 C30 C43 117.71(16) . . ?
O10 C30 C31 122.60(16) . . ?
C43 C30 C31 119.67(17) . . ?
C40 C31 C30 119.76(17) . . ?
C40 C31 H31A 120.1 . . ?
C30 C31 H31A 120.1 . . ?
C42 C43 C30 119.94(18) . . ?
C42 C43 H43A 120.0 . . ?
C30 C43 H43A 120.0 . . ?
C40 C41 C42 119.20(18) . . ?
C40 C41 H41A 120.4 . . ?
C42 C41 H41A 120.4 . . ?
C43 C42 C41 120.71(17) . . ?
C43 C42 H42A 119.6 . . ?
C41 C42 H42A 119.6 . . ?
C41 C40 C31 120.71(18) . . ?
C41 C40 H40A 119.6 . . ?
C31 C40 H40A 119.6 . . ?

_diffrn_measured_fraction_theta_max 0.986
_diffrn_reflns_theta_full        27.43
_diffrn_measured_fraction_theta_full 0.986
_refine_diff_density_max         0.287
_refine_diff_density_min         -0.204
_refine_diff_density_rms         0.044