# Supplementary Material (ESI) for Perkin Transactions
# This journal is © The Royal Society of Chemistry 2000
# CCDC Number: 207/455

data_adm128x 
 
_audit_creation_method            SHELXL 
_chemical_name_systematic 
; 
 compound 3f
; 
_chemical_name_common             ? 
_chemical_formula_moiety          ? 
_chemical_formula_structural      ? 
_chemical_formula_analytical      ? 
_chemical_formula_sum             'C26 H28 O S' 
_chemical_formula_weight          388.54 
_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' 
 'S'  'S'   0.1246   0.1234 
 '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)/c
 
loop_ 
 _symmetry_equiv_pos_as_xyz 
 'x, y, z' 
 '-x, y+1/2, -z+1/2' 
 '-x, -y, -z' 
 'x, -y-1/2, z-1/2' 
 
_cell_length_a                    13.131(2) 
_cell_length_b                    14.125(2) 
_cell_length_c                    11.6791(14) 
_cell_angle_alpha                 90.00 
_cell_angle_beta                  97.061(12) 
_cell_angle_gamma                 90.00 
_cell_volume                      2149.8(5) 
_cell_formula_units_Z             4 
_cell_measurement_temperature     150(2) 
_cell_measurement_reflns_used     39
_cell_measurement_theta_min       10
_cell_measurement_theta_max       12.5
 
_exptl_crystal_description        plates
_exptl_crystal_colour             none
_exptl_crystal_size_max           0.80 
_exptl_crystal_size_mid           0.60 
_exptl_crystal_size_min           0.40 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_diffrn     1.200 
_exptl_crystal_density_method     ? 
_exptl_crystal_F_000              832 
_exptl_absorpt_coefficient_mu     0.164 
_exptl_absorpt_correction_type    none
_exptl_absorpt_correction_T_min   ? 
_exptl_absorpt_correction_T_max   ? 
 
_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        'STOE AED2 four circle diffractometer'
_diffrn_measurement_method        'profile fitted theta omega scans'
_diffrn_standards_number          3
_diffrn_standards_interval_count  '90 min' 
_diffrn_standards_interval_time   ? 
_diffrn_standards_decay_%         none
_diffrn_reflns_number             2837 
_diffrn_reflns_av_R_equivalents   0.0629 
_diffrn_reflns_av_sigmaI/netI     0.0321 
_diffrn_reflns_limit_h_min        -12 
_diffrn_reflns_limit_h_max        14 
_diffrn_reflns_limit_k_min        -15 
_diffrn_reflns_limit_k_max        0 
_diffrn_reflns_limit_l_min        -12 
_diffrn_reflns_limit_l_max        12 
_diffrn_reflns_theta_min          3.52 
_diffrn_reflns_theta_max          22.52 
_reflns_number_total              2812 
_reflns_number_observed           2308 
_reflns_observed_criterion        >2sigma(I) 
 
_computing_data_collection        'STOE DIF4'
_computing_cell_refinement        'STOE DIF4'
_computing_data_reduction         'STOE REDU4'
_computing_structure_solution     'SHELXS-86 (Sheldrick, 1990)' 
_computing_structure_refinement   'SHELXL-93 (Sheldrick, 1993)' 
_computing_molecular_graphics     SHELXTL
_computing_publication_material   SHELXTL
 
_refine_special_details 
; 
 Refinement on F^2^ for ALL reflections except for 5 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^)+(0.0420P)^2^+1.4400P] 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     riding
_refine_ls_extinction_method      none 
_refine_ls_extinction_coef        ? 
_refine_ls_number_reflns          2807 
_refine_ls_number_parameters      255 
_refine_ls_number_restraints      0 
_refine_ls_R_factor_all           0.0553 
_refine_ls_R_factor_obs           0.0419 
_refine_ls_wR_factor_all          0.1072 
_refine_ls_wR_factor_obs          0.0930 
_refine_ls_goodness_of_fit_all    1.083 
_refine_ls_goodness_of_fit_obs    1.067 
_refine_ls_restrained_S_all       1.104 
_refine_ls_restrained_S_obs       1.067 
_refine_ls_shift/esd_max          0.000 
_refine_ls_shift/esd_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_thermal_displace_type 
 _atom_site_occupancy 
 _atom_site_calc_flag 
 _atom_site_refinement_flags 
 _atom_site_disorder_group 
C1' C 0.3029(2) 0.9721(2) 0.0681(2) 0.0253(6) Uani 1 d . . 
C2 C 0.1429(2) 0.8941(2) -0.0533(2) 0.0386(7) Uani 1 d . . 
H2A H 0.1478(2) 0.9445(2) -0.1112(2) 0.046 Uiso 1 calc R . 
H2B H 0.1206(2) 0.8316(2) -0.0857(2) 0.046 Uiso 1 calc R . 
C2' C 0.2196(2) 0.8956(2) 0.0540(2) 0.0281(6) Uani 1 d . . 
C2" C 0.2313(2) 0.7089(2) 0.0700(2) 0.0400(7) Uani 1 d . . 
H2"A H 0.2836(2) 0.6594(2) 0.0633(2) 0.048 Uiso 1 calc R . 
H2"B H 0.1693(2) 0.7044(2) 0.0127(2) 0.048 Uiso 1 calc R . 
C3 C 0.1089(2) 0.9221(2) 0.0603(2) 0.0389(7) Uani 1 d . . 
H3A H 0.0658(2) 0.8767(2) 0.0976(2) 0.047 Uiso 1 calc R . 
H3B H 0.0930(2) 0.9896(2) 0.0721(2) 0.047 Uiso 1 calc R . 
C3' C 0.2681(2) 0.8057(2) 0.1077(2) 0.0266(6) Uani 1 d . . 
C3" C 0.2177(2) 0.7440(2) 0.1897(2) 0.0374(7) Uani 1 d . . 
H3"A H 0.1476(2) 0.7611(2) 0.2053(2) 0.045 Uiso 1 calc R . 
H3"B H 0.2619(2) 0.7160(2) 0.2559(2) 0.045 Uiso 1 calc R . 
C4' C 0.3833(2) 0.8266(2) 0.1414(2) 0.0232(6) Uani 1 d . . 
C5' C 0.3903(2) 0.9017(2) 0.2349(2) 0.0227(6) Uani 1 d . . 
C6' C 0.3441(2) 0.9818(2) 0.1951(2) 0.0237(6) Uani 1 d . . 
S7' S 0.41589(5) 0.90593(4) 0.02513(5) 0.0253(2) Uani 1 d . . 
O7 O 0.39097(14) 0.86060(13) -0.09043(14) 0.0345(5) Uani 1 d . . 
C11 C 0.2831(2) 1.0636(2) 0.0012(2) 0.0359(7) Uani 1 d . . 
H11A H 0.2739(13) 1.0499(2) -0.0817(2) 0.054 Uiso 1 calc R . 
H11B H 0.3417(6) 1.1063(5) 0.0193(11) 0.054 Uiso 1 calc R . 
H11C H 0.2210(8) 1.0937(6) 0.0227(11) 0.054 Uiso 1 calc R . 
C41 C 0.4547(2) 0.7424(2) 0.1601(2) 0.0293(6) Uani 1 d . . 
H41A H 0.4482(9) 0.7034(6) 0.0901(5) 0.044 Uiso 1 calc R . 
H41B H 0.4364(8) 0.7046(6) 0.2249(9) 0.044 Uiso 1 calc R . 
H41C H 0.5256(2) 0.7646(2) 0.1773(14) 0.044 Uiso 1 calc R . 
C50 C 0.4432(2) 0.8826(2) 0.3545(2) 0.0261(6) Uani 1 d . . 
H50A H 0.4253(2) 0.8179(2) 0.3779(2) 0.031 Uiso 1 calc R . 
H50B H 0.4173(2) 0.9277(2) 0.4089(2) 0.031 Uiso 1 calc R . 
C51 C 0.5597(2) 0.8913(2) 0.3634(2) 0.0242(6) Uani 1 d . . 
C52 C 0.6049(2) 0.9663(2) 0.3120(2) 0.0308(6) Uani 1 d . . 
H52A H 0.5629(2) 1.0126(2) 0.2704(2) 0.037 Uiso 1 calc R . 
C53 C 0.7115(2) 0.9743(2) 0.3208(2) 0.0392(7) Uani 1 d . . 
H53A H 0.7419(2) 1.0261(2) 0.2858(2) 0.047 Uiso 1 calc R . 
C54 C 0.7725(2) 0.9064(2) 0.3807(2) 0.0407(8) Uani 1 d . . 
H54A H 0.8451(2) 0.9115(2) 0.3866(2) 0.049 Uiso 1 calc R . 
C55 C 0.7286(2) 0.8317(2) 0.4318(2) 0.0378(7) Uani 1 d . . 
H55A H 0.7707(2) 0.7854(2) 0.4731(2) 0.045 Uiso 1 calc R . 
C56 C 0.6223(2) 0.8241(2) 0.4229(2) 0.0319(7) Uani 1 d . . 
H56A H 0.5923(2) 0.7721(2) 0.4580(2) 0.038 Uiso 1 calc R . 
C60 C 0.3278(2) 1.0696(2) 0.2625(2) 0.0289(6) Uani 1 d . . 
H60A H 0.3444(2) 1.1257(2) 0.2174(2) 0.035 Uiso 1 calc R . 
H60B H 0.3751(2) 1.0689(2) 0.3353(2) 0.035 Uiso 1 calc R . 
C61 C 0.2176(2) 1.0779(2) 0.2905(2) 0.0290(6) Uani 1 d . . 
C62 C 0.1697(2) 1.0010(2) 0.3339(2) 0.0352(7) Uani 1 d . . 
H62A H 0.2055(2) 0.9426(2) 0.3448(2) 0.042 Uiso 1 calc R . 
C63 C 0.0698(2) 1.0075(2) 0.3618(2) 0.0443(8) Uani 1 d . . 
H63A H 0.0380(2) 0.9543(2) 0.3923(2) 0.053 Uiso 1 calc R . 
C64 C 0.0175(2) 1.0921(3) 0.3447(3) 0.0525(9) Uani 1 d . . 
H64A H -0.0509(2) 1.0972(3) 0.3626(3) 0.063 Uiso 1 calc R . 
C65 C 0.0645(2) 1.1688(3) 0.3018(3) 0.0549(9) Uani 1 d . . 
H65A H 0.0285(2) 1.2270(3) 0.2907(3) 0.066 Uiso 1 calc R . 
C66 C 0.1644(2) 1.1620(2) 0.2744(2) 0.0421(8) Uani 1 d . . 
H66A H 0.1961(2) 1.2155(2) 0.2445(2) 0.051 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 
C1' 0.0252(14) 0.0267(14) 0.0247(14) 0.0001(11) 0.0063(11) 0.0029(11) 
C2 0.033(2) 0.048(2) 0.032(2) -0.0021(14) -0.0049(12) -0.0014(14) 
C2' 0.0224(14) 0.033(2) 0.0286(15) -0.0011(12) 0.0027(11) 0.0006(12) 
C2" 0.041(2) 0.035(2) 0.043(2) -0.0024(14) -0.0017(13) -0.0086(14) 
C3 0.0241(15) 0.049(2) 0.043(2) 0.0019(15) 0.0023(12) 0.0029(14) 
C3' 0.0240(13) 0.030(2) 0.0263(14) -0.0004(12) 0.0056(11) -0.0045(12) 
C3" 0.029(2) 0.041(2) 0.043(2) 0.0070(14) 0.0075(13) -0.0102(13) 
C4' 0.0218(13) 0.0251(14) 0.0238(14) 0.0004(11) 0.0076(11) -0.0008(11) 
C5' 0.0169(12) 0.0282(15) 0.0243(14) 0.0005(11) 0.0074(10) -0.0034(11) 
C6' 0.0161(13) 0.0280(15) 0.0282(14) -0.0016(12) 0.0068(11) -0.0017(11) 
S7' 0.0265(4) 0.0249(4) 0.0261(4) 0.0011(3) 0.0096(3) 0.0005(3) 
O7 0.0474(11) 0.0344(11) 0.0234(10) -0.0026(8) 0.0105(8) 0.0038(9) 
C11 0.041(2) 0.034(2) 0.033(2) 0.0042(13) 0.0070(13) 0.0082(13) 
C41 0.0340(15) 0.0257(15) 0.0290(14) 0.0026(12) 0.0068(12) 0.0015(12) 
C50 0.0251(14) 0.0284(15) 0.0255(14) 0.0012(11) 0.0062(11) -0.0009(11) 
C51 0.0251(13) 0.0280(14) 0.0192(13) -0.0050(11) 0.0019(10) -0.0018(12) 
C52 0.030(2) 0.028(2) 0.034(2) -0.0029(12) 0.0033(12) -0.0032(12) 
C53 0.033(2) 0.043(2) 0.043(2) -0.0120(15) 0.0105(13) -0.0143(14) 
C54 0.0235(15) 0.055(2) 0.043(2) -0.019(2) 0.0006(13) -0.0040(15) 
C55 0.032(2) 0.048(2) 0.031(2) -0.0053(14) -0.0039(13) 0.0083(14) 
C56 0.035(2) 0.037(2) 0.0240(14) -0.0008(12) 0.0037(12) 0.0019(13) 
C60 0.0255(14) 0.030(2) 0.0313(15) -0.0026(12) 0.0045(11) 0.0013(12) 
C61 0.0292(14) 0.035(2) 0.0231(14) -0.0061(12) 0.0038(11) 0.0050(13) 
C62 0.028(2) 0.044(2) 0.035(2) -0.0023(14) 0.0079(12) 0.0054(13) 
C63 0.032(2) 0.064(2) 0.039(2) -0.003(2) 0.0117(13) -0.001(2) 
C64 0.028(2) 0.085(3) 0.046(2) -0.007(2) 0.0088(14) 0.015(2) 
C65 0.043(2) 0.065(2) 0.057(2) 0.000(2) 0.007(2) 0.030(2) 
C66 0.042(2) 0.043(2) 0.041(2) 0.0010(14) 0.0050(14) 0.0147(15) 
 
_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 
C1' C11 1.516(4) . ? 
C1' C6' 1.521(3) . ? 
C1' C2' 1.532(4) . ? 
C1' S7' 1.874(2) . ? 
C2 C3 1.504(4) . ? 
C2 C2' 1.508(4) . ? 
C2' C3 1.512(4) . ? 
C2' C3' 1.520(4) . ? 
C2" C3' 1.499(4) . ? 
C2" C3" 1.514(4) . ? 
C3' C3" 1.507(4) . ? 
C3' C4' 1.543(3) . ? 
C4' C41 1.513(3) . ? 
C4' C5' 1.517(3) . ? 
C4' S7' 1.851(2) . ? 
C5' C6' 1.339(3) . ? 
C5' C50 1.506(3) . ? 
C6' C60 1.498(4) . ? 
S7' O7 1.493(2) . ? 
C50 C51 1.526(3) . ? 
C51 C56 1.385(4) . ? 
C51 C52 1.386(4) . ? 
C52 C53 1.395(4) . ? 
C53 C54 1.384(4) . ? 
C54 C55 1.373(4) . ? 
C55 C56 1.391(4) . ? 
C60 C61 1.527(3) . ? 
C61 C66 1.379(4) . ? 
C61 C62 1.383(4) . ? 
C62 C63 1.393(4) . ? 
C63 C64 1.381(4) . ? 
C64 C65 1.371(5) . ? 
C65 C66 1.391(4) . ? 
 
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 
C11 C1' C6' 116.3(2) . . ? 
C11 C1' C2' 118.1(2) . . ? 
C6' C1' C2' 109.4(2) . . ? 
C11 C1' S7' 112.2(2) . . ? 
C6' C1' S7' 96.2(2) . . ? 
C2' C1' S7' 101.4(2) . . ? 
C3 C2 C2' 60.3(2) . . ? 
C2 C2' C3 59.8(2) . . ? 
C2 C2' C3' 122.3(2) . . ? 
C3 C2' C3' 122.9(2) . . ? 
C2 C2' C1' 119.6(2) . . ? 
C3 C2' C1' 119.9(2) . . ? 
C3' C2' C1' 106.7(2) . . ? 
C3' C2" C3" 60.0(2) . . ? 
C2 C3 C2' 60.0(2) . . ? 
C2" C3' C3" 60.5(2) . . ? 
C2" C3' C2' 122.5(2) . . ? 
C3" C3' C2' 123.4(2) . . ? 
C2" C3' C4' 121.3(2) . . ? 
C3" C3' C4' 116.2(2) . . ? 
C2' C3' C4' 107.1(2) . . ? 
C3' C3" C2" 59.5(2) . . ? 
C41 C4' C5' 117.7(2) . . ? 
C41 C4' C3' 117.2(2) . . ? 
C5' C4' C3' 106.7(2) . . ? 
C41 C4' S7' 112.7(2) . . ? 
C5' C4' S7' 96.1(2) . . ? 
C3' C4' S7' 103.6(2) . . ? 
C6' C5' C50 127.7(2) . . ? 
C6' C5' C4' 110.9(2) . . ? 
C50 C5' C4' 121.4(2) . . ? 
C5' C6' C60 127.2(2) . . ? 
C5' C6' C1' 110.7(2) . . ? 
C60 C6' C1' 122.0(2) . . ? 
O7 S7' C4' 111.02(11) . . ? 
O7 S7' C1' 111.29(11) . . ? 
C4' S7' C1' 80.98(11) . . ? 
C5' C50 C51 113.2(2) . . ? 
C56 C51 C52 118.8(2) . . ? 
C56 C51 C50 120.5(2) . . ? 
C52 C51 C50 120.7(2) . . ? 
C51 C52 C53 120.6(3) . . ? 
C54 C53 C52 119.6(3) . . ? 
C55 C54 C53 120.3(3) . . ? 
C54 C55 C56 119.9(3) . . ? 
C51 C56 C55 120.8(3) . . ? 
C6' C60 C61 112.2(2) . . ? 
C66 C61 C62 118.7(2) . . ? 
C66 C61 C60 121.0(3) . . ? 
C62 C61 C60 120.3(2) . . ? 
C61 C62 C63 121.2(3) . . ? 
C64 C63 C62 119.2(3) . . ? 
C65 C64 C63 119.9(3) . . ? 
C64 C65 C66 120.6(3) . . ? 
C61 C66 C65 120.3(3) . . ? 
 
_refine_diff_density_max    0.217 
_refine_diff_density_min   -0.239 
_refine_diff_density_rms    0.046