# Supplementary Material (ESI) for Perkin Transactions 1
# This journal is © The Royal Society of Chemistry 2002


data_sw9902 

_database_code_CSD	192685


_journal_coden_Cambridge      207


loop_
_publ_author_name
'Stuart Warren'
'David House'
'Fraser Kerr'

_publ_contact_author_name     	'Dr Stuart Warren'  
_publ_contact_author_address 
;
University Chemical Laboratories
University of Cambridge
Lensfield Road
Cambridge
Cambridgeshire
CB2 1EW
UNITED KINGDOM
;

_publ_contact_author_email       'SW134@CAM.AC.UK'

_publ_requested_journal       'Perkin Transactions 1'


_publ_section_title		
;
Scope and limitation of the [1,2]-phenylsulfanyl (PhS)
migration in the synthesis of tetrahydrofurans and tetrahydropyrans from
common triol precursors
;

_audit_creation_method            SHELXL 
_chemical_name_systematic 
; 
? 
; 
_chemical_name_common             ? 
_chemical_formula_moiety          ? 
_chemical_formula_structural      ? 
_chemical_formula_analytical      ? 
_chemical_formula_sum             'C20 H34 O3 S Si' 
_chemical_formula_weight          382.62 
_chemical_melting_point           ? 
_chemical_compound_source         ? 

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' 
'S'  'S'   0.1246   0.1234 
'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 

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

_cell_length_a                    10.820(3) 
_cell_length_b                    13.543(4) 
_cell_length_c                    7.720(2) 
_cell_angle_alpha                 91.37(3) 
_cell_angle_beta                  97.96(2) 
_cell_angle_gamma                 87.39(2) 
_cell_volume                      1119.0(5) 
_cell_formula_units_Z             2 
_cell_measurement_temperature     230(2) 
_cell_measurement_reflns_used     25
_cell_measurement_theta_min       10 
_cell_measurement_theta_max       20

_exptl_crystal_description        ? 
_exptl_crystal_colour             colourless
_exptl_crystal_size_max           0.30 
_exptl_crystal_size_mid           0.18 
_exptl_crystal_size_min           0.10 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_diffrn     1.136 
_exptl_crystal_density_method     ? 
_exptl_crystal_F_000              416 
_exptl_absorpt_coefficient_mu     0.213 
_exptl_absorpt_correction_type    empirical
_exptl_absorpt_correction_T_min   0.915
_exptl_absorpt_correction_T_max   1.000 

_exptl_special_details 
; 
? 
; 

_diffrn_ambient_temperature       230(2) 
_diffrn_radiation_wavelength      0.71069 
_diffrn_radiation_type            MoK\a 
_diffrn_radiation_source          'fine-focus sealed tube' 
_diffrn_radiation_monochromator   graphite 
_diffrn_measurement_device        AFC7R 
_diffrn_measurement_method        'omega/2theta scans'
_diffrn_standards_number          3 
_diffrn_standards_interval_count  200 
_diffrn_standards_interval_time   ? 
_diffrn_standards_decay_%         +0.1%
_diffrn_reflns_number             6366 
_diffrn_reflns_av_R_equivalents   0.0415 
_diffrn_reflns_av_sigmaI/netI     0.1059 
_diffrn_reflns_limit_h_min        0 
_diffrn_reflns_limit_h_max        12 
_diffrn_reflns_limit_k_min        -16 
_diffrn_reflns_limit_k_max        16 
_diffrn_reflns_limit_l_min        -9 
_diffrn_reflns_limit_l_max        9 
_diffrn_reflns_theta_min          2.66 
_diffrn_reflns_theta_max          25.01 
_reflns_number_total              3924 
_reflns_number_observed           2219 
_reflns_observed_criterion        >2sigma(I) 

_computing_data_collection        ? 
_computing_cell_refinement        ? 
_computing_data_reduction         ? 
_computing_structure_solution     'teXsan' 
_computing_structure_refinement   'SHELXL-93 (Sheldrick, 1993)' 
_computing_molecular_graphics     ? 
_computing_publication_material   ? 

_refine_special_details 
; 
Refinement on F^2^ for ALL reflections except for 0 with very negative F^2^ 
or flagged by the user for potential systematic errors.  Weighted R-factors 
wR and all goodnesses 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 observed criterion 
of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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^)+(0.0538P)^2^+0.0762P] 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     ? 
_refine_ls_extinction_method      none 
_refine_ls_extinction_coef        ? 
_refine_ls_number_reflns          3924 
_refine_ls_number_parameters      237 
_refine_ls_number_restraints      0 
_refine_ls_R_factor_all           0.1327 
_refine_ls_R_factor_obs           0.0620 
_refine_ls_wR_factor_all          0.1359 
_refine_ls_wR_factor_obs          0.1102 
_refine_ls_goodness_of_fit_all    1.019 
_refine_ls_goodness_of_fit_obs    1.122 
_refine_ls_restrained_S_all       1.019 
_refine_ls_restrained_S_obs       1.122 
_refine_ls_shift/esd_max          0.052 
_refine_ls_shift/esd_mean         0.004 

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_thermal_displace_type 
_atom_site_occupancy 
_atom_site_calc_flag 
_atom_site_refinement_flags 
_atom_site_disorder_group 
S1 S 0.25020(9) 0.23178(6) 0.20469(13) 0.0477(3) Uani 1 d . . 
Si1 Si 0.72492(9) 0.12581(7) 0.82170(13) 0.0366(3) Uani 1 d . . 
O1 O 0.6852(2) 0.24282(14) 0.7833(3) 0.0348(6) Uani 1 d . . 
O2 O 0.5760(2) 0.3889(2) 0.3968(3) 0.0423(7) Uani 1 d . . 
H2O H 0.6012(34) 0.4384(25) 0.4141(50) 0.051 Uiso 1 d . . 
O3 O 0.3225(2) 0.4275(2) 0.5149(3) 0.0450(6) Uani 1 d . . 
C1 C 0.8056(3) 0.3540(3) 0.6444(5) 0.0498(10) Uani 1 d . . 
H1A H 0.8809(3) 0.3125(3) 0.6715(26) 0.060 Uiso 1 calc R . 
H1B H 0.7989(9) 0.4012(10) 0.7395(17) 0.060 Uiso 1 calc R . 
H1C H 0.8092(11) 0.3892(11) 0.5374(9) 0.060 Uiso 1 calc R . 
C2 C 0.6933(3) 0.2905(2) 0.6208(4) 0.0336(8) Uani 1 d . . 
H2 H 0.7045(3) 0.2391(2) 0.5302(4) 0.040 Uiso 1 calc R . 
C3 C 0.5717(3) 0.3491(2) 0.5661(4) 0.0343(8) Uani 1 d . . 
H3 H 0.5618(3) 0.4035(2) 0.6516(4) 0.041 Uiso 1 calc R . 
C4 C 0.4588(3) 0.2845(2) 0.5496(5) 0.0363(9) Uani 1 d . . 
H4A H 0.4693(3) 0.2319(2) 0.4628(5) 0.044 Uiso 1 calc R . 
H4B H 0.4568(3) 0.2530(2) 0.6621(5) 0.044 Uiso 1 calc R . 
C5 C 0.3356(3) 0.3388(2) 0.4973(4) 0.0336(8) Uani 1 d . . 
C6 C 0.2223(3) 0.2793(2) 0.4235(4) 0.0358(8) Uani 1 d . . 
C7 C 0.2154(3) 0.1866(3) 0.5317(5) 0.0544(11) Uani 1 d . . 
H7A H 0.1435(11) 0.1499(8) 0.4826(16) 0.065 Uiso 1 calc R . 
H7B H 0.2074(19) 0.2060(3) 0.6516(8) 0.065 Uiso 1 calc R . 
H7C H 0.2909(9) 0.1454(8) 0.5295(22) 0.065 Uiso 1 calc R . 
C8 C 0.1031(3) 0.3418(3) 0.4136(5) 0.0487(10) Uani 1 d . . 
H8A H 0.0340(4) 0.3039(5) 0.3583(23) 0.058 Uiso 1 calc R . 
H8B H 0.1100(7) 0.4000(8) 0.3454(22) 0.058 Uiso 1 calc R . 
H8C H 0.0883(10) 0.3618(12) 0.5307(5) 0.058 Uiso 1 calc R . 
C9 C 0.6060(4) 0.0465(2) 0.7013(5) 0.0546(11) Uani 1 d . . 
H9A H 0.6042(13) 0.0547(11) 0.5765(5) 0.066 Uiso 1 calc R . 
H9B H 0.5247(5) 0.0652(10) 0.7340(20) 0.066 Uiso 1 calc R . 
H9C H 0.6268(11) -0.0221(3) 0.7304(21) 0.066 Uiso 1 calc R . 
C10 C 0.8778(4) 0.0911(3) 0.7500(6) 0.0644(12) Uani 1 d . . 
H10A H 0.8736(7) 0.1031(15) 0.6259(8) 0.077 Uiso 1 calc R . 
H10B H 0.8979(10) 0.0216(5) 0.7720(27) 0.077 Uiso 1 calc R . 
H10C H 0.9420(5) 0.1306(12) 0.8146(21) 0.077 Uiso 1 calc R . 
C11 C 0.7312(3) 0.1151(2) 1.0643(4) 0.0406(9) Uani 1 d . . 
C12 C 0.6074(4) 0.1535(3) 1.1184(5) 0.0659(12) Uani 1 d . . 
H12A H 0.5400(4) 0.1162(11) 1.0564(22) 0.079 Uiso 1 calc R . 
H12B H 0.5939(10) 0.2228(5) 1.0900(27) 0.079 Uiso 1 calc R . 
H12C H 0.6095(8) 0.1458(15) 1.2434(7) 0.079 Uiso 1 calc R . 
C13 C 0.7542(4) 0.0074(3) 1.1187(5) 0.0672(12) Uani 1 d . . 
H13A H 0.8323(11) -0.0182(6) 1.0832(27) 0.081 Uiso 1 calc R . 
H13B H 0.6863(11) -0.0315(4) 1.0626(24) 0.081 Uiso 1 calc R . 
H13C H 0.7587(21) 0.0033(3) 1.2447(6) 0.081 Uiso 1 calc R . 
C14 C 0.8357(4) 0.1766(3) 1.1589(5) 0.0677(12) Uani 1 d . . 
H14A H 0.9151(5) 0.1525(11) 1.1261(23) 0.081 Uiso 1 calc R . 
H14B H 0.8376(14) 0.1711(14) 1.2843(5) 0.081 Uiso 1 calc R . 
H14C H 0.8206(12) 0.2453(4) 1.1264(23) 0.081 Uiso 1 calc R . 
C15 C 0.2348(3) 0.3397(2) 0.0755(4) 0.0386(9) Uani 1 d . . 
C16 C 0.3353(3) 0.3986(3) 0.0703(5) 0.0523(10) Uani 1 d . . 
H16 H 0.4130(3) 0.3825(3) 0.1361(5) 0.063 Uiso 1 calc R . 
C17 C 0.3202(4) 0.4818(3) -0.0331(5) 0.0622(12) Uani 1 d . . 
H17 H 0.3880(4) 0.5223(3) -0.0366(5) 0.075 Uiso 1 calc R . 
C18 C 0.2077(4) 0.5055(3) -0.1299(5) 0.0553(11) Uani 1 d . . 
H18 H 0.1986(4) 0.5620(3) -0.1996(5) 0.066 Uiso 1 calc R . 
C19 C 0.1081(4) 0.4468(3) -0.1256(5) 0.0537(11) Uani 1 d . . 
H19 H 0.0308(4) 0.4632(3) -0.1923(5) 0.064 Uiso 1 calc R . 
C20 C 0.1215(3) 0.3640(3) -0.0234(5) 0.0484(10) Uani 1 d . . 
H20 H 0.0532(3) 0.3239(3) -0.0209(5) 0.058 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 
S1 0.0557(7) 0.0381(5) 0.0475(6) -0.0043(5) 0.0034(5) 0.0014(5) 
Si1 0.0393(6) 0.0329(6) 0.0370(6) 0.0051(4) 0.0031(5) 0.0008(4) 
O1 0.0394(14) 0.0319(12) 0.0331(14) 0.0077(10) 0.0036(11) 0.0001(10) 
O2 0.049(2) 0.0373(14) 0.040(2) 0.0105(13) -0.0011(12) -0.0138(12) 
O3 0.0434(15) 0.0304(15) 0.061(2) 0.0012(12) 0.0053(12) -0.0039(11) 
C1 0.039(2) 0.056(2) 0.054(3) 0.015(2) 0.001(2) -0.008(2) 
C2 0.032(2) 0.035(2) 0.034(2) 0.001(2) 0.005(2) -0.007(2) 
C3 0.038(2) 0.031(2) 0.034(2) 0.005(2) 0.002(2) -0.007(2) 
C4 0.032(2) 0.029(2) 0.047(2) 0.010(2) -0.001(2) -0.004(2) 
C5 0.040(2) 0.030(2) 0.033(2) 0.006(2) 0.012(2) -0.004(2) 
C6 0.031(2) 0.036(2) 0.041(2) 0.004(2) 0.005(2) -0.006(2) 
C7 0.055(3) 0.049(2) 0.061(3) 0.009(2) 0.008(2) -0.020(2) 
C8 0.034(2) 0.060(2) 0.053(3) -0.007(2) 0.007(2) -0.007(2) 
C9 0.070(3) 0.039(2) 0.052(3) -0.001(2) -0.004(2) -0.004(2) 
C10 0.060(3) 0.064(3) 0.072(3) 0.008(2) 0.021(2) 0.015(2) 
C11 0.044(2) 0.035(2) 0.042(2) 0.005(2) -0.001(2) -0.008(2) 
C12 0.078(3) 0.075(3) 0.048(3) 0.003(2) 0.018(2) -0.011(2) 
C13 0.088(3) 0.058(3) 0.054(3) 0.022(2) -0.002(2) -0.007(2) 
C14 0.074(3) 0.080(3) 0.046(3) 0.000(2) -0.009(2) -0.026(3) 
C15 0.040(2) 0.044(2) 0.031(2) -0.006(2) 0.004(2) 0.000(2) 
C16 0.040(2) 0.074(3) 0.042(2) 0.010(2) 0.002(2) -0.007(2) 
C17 0.060(3) 0.078(3) 0.051(3) 0.019(2) 0.007(2) -0.018(2) 
C18 0.068(3) 0.060(3) 0.038(3) 0.010(2) 0.007(2) 0.006(2) 
C19 0.046(3) 0.072(3) 0.041(3) 0.004(2) -0.001(2) 0.005(2) 
C20 0.043(2) 0.057(3) 0.045(2) -0.006(2) 0.001(2) -0.009(2) 

_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 
S1 C15 1.777(4) . ? 
S1 C6 1.852(3) . ? 
Si1 O1 1.646(2) . ? 
Si1 C9 1.849(4) . ? 
Si1 C10 1.853(4) . ? 
Si1 C11 1.873(4) . ? 
O1 C2 1.440(4) . ? 
O2 C3 1.434(4) . ? 
O3 C5 1.210(3) . ? 
C1 C2 1.509(4) . ? 
C2 C3 1.518(4) . ? 
C3 C4 1.524(4) . ? 
C4 C5 1.502(4) . ? 
C5 C6 1.533(4) . ? 
C6 C8 1.504(4) . ? 
C6 C7 1.535(4) . ? 
C11 C12 1.523(5) . ? 
C11 C14 1.527(5) . ? 
C11 C13 1.528(5) . ? 
C15 C20 1.382(5) . ? 
C15 C16 1.384(5) . ? 
C16 C17 1.386(5) . ? 
C17 C18 1.366(5) . ? 
C18 C19 1.372(5) . ? 
C19 C20 1.377(5) . ? 

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 
C15 S1 C6 103.43(15) . . ? 
O1 Si1 C9 109.71(14) . . ? 
O1 Si1 C10 111.34(15) . . ? 
C9 Si1 C10 108.3(2) . . ? 
O1 Si1 C11 104.35(14) . . ? 
C9 Si1 C11 111.7(2) . . ? 
C10 Si1 C11 111.5(2) . . ? 
C2 O1 Si1 124.2(2) . . ? 
O1 C2 C1 108.9(3) . . ? 
O1 C2 C3 108.6(2) . . ? 
C1 C2 C3 112.9(3) . . ? 
O2 C3 C2 108.3(3) . . ? 
O2 C3 C4 107.1(3) . . ? 
C2 C3 C4 112.2(2) . . ? 
C5 C4 C3 114.6(3) . . ? 
O3 C5 C4 122.1(3) . . ? 
O3 C5 C6 119.1(3) . . ? 
C4 C5 C6 118.8(3) . . ? 
C8 C6 C5 111.3(3) . . ? 
C8 C6 C7 111.1(3) . . ? 
C5 C6 C7 110.8(3) . . ? 
C8 C6 S1 111.5(2) . . ? 
C5 C6 S1 107.0(2) . . ? 
C7 C6 S1 104.9(2) . . ? 
C12 C11 C14 108.7(3) . . ? 
C12 C11 C13 108.8(3) . . ? 
C14 C11 C13 109.2(3) . . ? 
C12 C11 Si1 109.4(2) . . ? 
C14 C11 Si1 110.1(2) . . ? 
C13 C11 Si1 110.6(3) . . ? 
C20 C15 C16 119.6(3) . . ? 
C20 C15 S1 119.6(3) . . ? 
C16 C15 S1 120.8(3) . . ? 
C15 C16 C17 119.3(3) . . ? 
C18 C17 C16 120.7(4) . . ? 
C17 C18 C19 120.1(4) . . ? 
C18 C19 C20 120.0(4) . . ? 
C19 C20 C15 120.4(4) . . ? 

_refine_diff_density_max    0.251 
_refine_diff_density_min   -0.241 
_refine_diff_density_rms    0.053