# Supplementary Material (ESI) for ChemComm
# This journal is © The Royal Society of Chemistry 2000
# CCDC Number: 182/1709

data_s92 
 
_audit_creation_method            SHELXL 
_chemical_name_systematic 
; 
 ? 
; 
_chemical_name_common             ? 
_chemical_formula_moiety          ? 
_chemical_formula_structural      ? 
_chemical_formula_analytical      ? 
_chemical_formula_sum             'C19 H20 O3 S' 
_chemical_formula_weight          328.41 
_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            ? 
_symmetry_space_group_name_H-M    ? 
 
loop_ 
 _symmetry_equiv_pos_as_xyz 
 'x, y, z' 
 '-x+1/2, y+1/2, -z+1/2' 
 '-x, -y, -z' 
 'x-1/2, -y-1/2, z-1/2' 
 
_cell_length_a                    10.773(2) 
_cell_length_b                    7.861(2) 
_cell_length_c                    19.492(4) 
_cell_angle_alpha                 90.00 
_cell_angle_beta                  92.42(3) 
_cell_angle_gamma                 90.00 
_cell_volume                      1649.2(6) 
_cell_formula_units_Z             4 
_cell_measurement_temperature     293(2) 
_cell_measurement_reflns_used     ? 
_cell_measurement_theta_min       ? 
_cell_measurement_theta_max       ? 
 
_exptl_crystal_description        ? 
_exptl_crystal_colour             ? 
_exptl_crystal_size_max           ? 
_exptl_crystal_size_mid           ? 
_exptl_crystal_size_min           ? 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_diffrn     1.323 
_exptl_crystal_density_method     ? 
_exptl_crystal_F_000              696 
_exptl_absorpt_coefficient_mu     0.209 
_exptl_absorpt_correction_type    ? 
_exptl_absorpt_correction_T_min   ? 
_exptl_absorpt_correction_T_max   ? 
 
_exptl_special_details 
; 
 ? 
; 
 
_diffrn_ambient_temperature       293(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        ? 
_diffrn_measurement_method        ? 
_diffrn_standards_number          ? 
_diffrn_standards_interval_count  ? 
_diffrn_standards_interval_time   ? 
_diffrn_standards_decay_%         ? 
_diffrn_reflns_number             6240 
_diffrn_reflns_av_R_equivalents   0.1522 
_diffrn_reflns_av_sigmaI/netI     0.1332 
_diffrn_reflns_limit_h_min        -9 
_diffrn_reflns_limit_h_max        11 
_diffrn_reflns_limit_k_min        -7 
_diffrn_reflns_limit_k_max        9 
_diffrn_reflns_limit_l_min        -21 
_diffrn_reflns_limit_l_max        20 
_diffrn_reflns_theta_min          2.09 
_diffrn_reflns_theta_max          25.00 
_reflns_number_total              2350 
_reflns_number_observed           1723 
_reflns_observed_criterion        >2sigma(I) 
 
_computing_data_collection        ? 
_computing_cell_refinement        ? 
_computing_data_reduction         ? 
_computing_structure_solution     'SHELXS-86 (Sheldrick, 1990)' 
_computing_structure_refinement   'SHELXL-92 (Sheldrick, 1993)' 
_computing_molecular_graphics     ? 
_computing_publication_material   ? 
 
_refine_special_details 
; 
 Refinement on F^2^ for ALL reflections except for 1 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^)+(0.0441P)^2^+0.0000P] 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          2349 
_refine_ls_number_parameters      211 
_refine_ls_number_restraints      0 
_refine_ls_R_factor_all           0.0686 
_refine_ls_R_factor_obs           0.0517 
_refine_ls_wR_factor_all          0.1179 
_refine_ls_wR_factor_obs          0.1090 
_refine_ls_goodness_of_fit_all    0.836 
_refine_ls_goodness_of_fit_obs    0.964 
_refine_ls_restrained_S_all       0.879 
_refine_ls_restrained_S_obs       0.964 
_refine_ls_shift/esd_max          0.001 
_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 
S1 S 0.61090(7) 0.12077(10) 0.20818(4) 0.0227(3) Uani 1 d . . 
O1 O 0.5091(2) -0.0487(3) 0.30636(12) 0.0255(5) Uani 1 d . . 
O2 O 0.6705(2) 0.0839(2) 0.07951(11) 0.0201(5) Uani 1 d . . 
O3 O 0.8473(2) -0.1774(2) -0.04530(11) 0.0182(5) Uani 1 d . . 
C1 C 0.5420(2) -0.0604(4) 0.2485(2) 0.0172(7) Uani 1 d . . 
C2 C 0.6354(2) 0.0087(4) 0.1292(2) 0.0145(7) Uani 1 d . . 
C3 C 0.6112(2) -0.1754(3) 0.13955(15) 0.0139(7) Uani 1 d . . 
C4 C 0.5315(2) -0.2046(4) 0.1983(2) 0.0140(7) Uani 1 d . . 
C5 C 0.6835(2) -0.2953(4) 0.10960(15) 0.0135(7) Uani 1 d . . 
C6 C 0.6897(2) -0.4754(4) 0.1342(2) 0.0185(7) Uani 1 d . . 
H6A H 0.7740(3) -0.5147(8) 0.1341(9) 0.028 Uiso 1 calc R . 
H6B H 0.6385(13) -0.5456(5) 0.1043(5) 0.028 Uiso 1 calc R . 
H6C H 0.6604(15) -0.4815(5) 0.1800(3) 0.028 Uiso 1 calc R . 
C7 C 0.7685(2) -0.2561(4) 0.0546(2) 0.0155(7) Uani 1 d . . 
C8 C 0.7423(2) -0.1875(4) -0.0079(2) 0.0143(7) Uani 1 d . . 
C9 C 0.6249(2) -0.1319(4) -0.0439(2) 0.0196(7) Uani 1 d . . 
H9A H 0.6143(9) -0.1919(17) -0.0866(5) 0.029 Uiso 1 calc R . 
H9B H 0.6285(7) -0.0118(6) -0.0526(9) 0.029 Uiso 1 calc R . 
H9C H 0.5562(3) -0.1561(22) -0.0156(4) 0.029 Uiso 1 calc R . 
C10 C 0.9449(2) -0.2421(4) -0.0040(2) 0.0166(7) Uani 1 d . . 
C11 C 1.0687(3) -0.2341(4) -0.0335(2) 0.0257(8) Uani 1 d . . 
H11A H 1.0930(8) -0.1174(4) -0.0383(10) 0.039 Uiso 1 calc R . 
H11B H 1.0656(5) -0.2881(23) -0.0777(5) 0.039 Uiso 1 calc R . 
H11C H 1.1280(4) -0.2917(22) -0.0036(5) 0.039 Uiso 1 calc R . 
C12 C 0.9007(2) -0.2952(4) 0.0559(2) 0.0171(7) Uani 1 d . . 
H12 H 0.9463(2) -0.3474(4) 0.0916(2) 0.021 Uiso 1 calc R . 
C13 C 0.4484(2) -0.3342(3) 0.2073(2) 0.0147(7) Uani 1 d . . 
C14 C 0.4072(2) -0.4497(4) 0.14980(15) 0.0161(7) Uani 1 d . . 
H14 H 0.4321(2) -0.5688(4) 0.15591(15) 0.019 Uiso 1 calc R . 
C15 C 0.3901(2) -0.3937(4) 0.0763(2) 0.0202(7) Uani 1 d . . 
H15A H 0.4105(2) -0.2768(4) 0.0655(2) 0.024 Uiso 1 calc R . 
H15B H 0.4083(2) -0.4755(4) 0.0408(2) 0.024 Uiso 1 calc R . 
C16 C 0.2780(3) -0.4244(4) 0.1170(2) 0.0254(8) Uani 1 d . . 
H16A H 0.2287(3) -0.5250(4) 0.1064(2) 0.030 Uiso 1 calc R . 
H16B H 0.2309(3) -0.3261(4) 0.1310(2) 0.030 Uiso 1 calc R . 
C17 C 0.3949(2) -0.3698(4) 0.2742(2) 0.0206(7) Uani 1 d . . 
H17 H 0.4083(2) -0.2795(4) 0.3084(2) 0.025 Uiso 1 calc R . 
C18 C 0.2794(3) -0.4729(5) 0.2830(2) 0.0377(9) Uani 1 d . . 
H18A H 0.2253(3) -0.4395(5) 0.3192(2) 0.045 Uiso 1 calc R . 
H18B H 0.2368(3) -0.5171(5) 0.2420(2) 0.045 Uiso 1 calc R . 
C19 C 0.3997(3) -0.5474(4) 0.3034(2) 0.0371(9) Uani 1 d . . 
H19A H 0.4314(3) -0.6373(4) 0.2749(2) 0.045 Uiso 1 calc R . 
H19B H 0.4199(3) -0.5597(4) 0.3521(2) 0.045 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 0.0292(5) 0.0124(4) 0.0266(5) -0.0034(4) 0.0023(3) -0.0043(3) 
O1 0.0251(13) 0.0280(13) 0.0237(14) -0.0082(11) 0.0035(10) -0.0079(9) 
O2 0.0197(12) 0.0123(12) 0.0286(14) 0.0037(10) 0.0048(9) -0.0011(8) 
O3 0.0122(11) 0.0186(12) 0.0238(13) 0.0020(9) -0.0005(9) -0.0002(8) 
C1 0.010(2) 0.021(2) 0.020(2) -0.0010(14) -0.0008(13) -0.0008(12) 
C2 0.007(2) 0.011(2) 0.026(2) -0.0010(14) -0.0005(12) 0.0010(11) 
C3 0.009(2) 0.013(2) 0.020(2) 0.0003(13) -0.0017(12) -0.0038(11) 
C4 0.0074(15) 0.013(2) 0.022(2) 0.0003(13) -0.0011(12) 0.0024(11) 
C5 0.0078(15) 0.013(2) 0.020(2) -0.0003(13) -0.0041(12) -0.0015(11) 
C6 0.014(2) 0.015(2) 0.027(2) 0.0022(14) 0.0025(13) 0.0005(11) 
C7 0.010(2) 0.012(2) 0.024(2) -0.0016(14) 0.0006(13) -0.0003(11) 
C8 0.006(2) 0.017(2) 0.020(2) -0.0022(14) 0.0052(13) 0.0019(11) 
C9 0.017(2) 0.020(2) 0.022(2) -0.0009(14) -0.0009(13) 0.0026(12) 
C10 0.010(2) 0.017(2) 0.023(2) 0.0002(14) 0.0004(13) 0.0011(11) 
C11 0.018(2) 0.027(2) 0.032(2) -0.002(2) 0.0035(14) -0.0014(13) 
C12 0.012(2) 0.013(2) 0.026(2) 0.0003(14) -0.0024(13) 0.0034(12) 
C13 0.010(2) 0.012(2) 0.022(2) -0.0008(13) 0.0001(12) 0.0045(11) 
C14 0.015(2) 0.011(2) 0.022(2) -0.0009(14) 0.0004(13) -0.0001(11) 
C15 0.018(2) 0.019(2) 0.023(2) -0.0039(15) -0.0027(14) -0.0026(12) 
C16 0.015(2) 0.029(2) 0.032(2) -0.009(2) -0.0034(14) -0.0028(13) 
C17 0.022(2) 0.018(2) 0.022(2) -0.0010(14) 0.0037(14) -0.0059(13) 
C18 0.031(2) 0.052(2) 0.030(2) -0.001(2) 0.009(2) -0.020(2) 
C19 0.059(3) 0.019(2) 0.035(2) 0.007(2) 0.018(2) 0.004(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 C1 1.802(3) . ? 
S1 C2 1.803(3) . ? 
O1 C1 1.200(3) . ? 
O2 C2 1.209(3) . ? 
O3 C8 1.374(3) . ? 
O3 C10 1.393(3) . ? 
C1 C4 1.499(4) . ? 
C2 C3 1.486(4) . ? 
C3 C5 1.369(4) . ? 
C3 C4 1.478(4) . ? 
C4 C13 1.373(4) . ? 
C5 C7 1.472(4) . ? 
C5 C6 1.495(4) . ? 
C7 C8 1.350(4) . ? 
C7 C12 1.456(4) . ? 
C8 C9 1.485(4) . ? 
C10 C12 1.346(4) . ? 
C10 C11 1.476(4) . ? 
C13 C17 1.474(4) . ? 
C13 C14 1.495(4) . ? 
C14 C15 1.503(4) . ? 
C14 C16 1.520(4) . ? 
C15 C16 1.492(4) . ? 
C17 C18 1.501(4) . ? 
C17 C19 1.508(4) . ? 
C18 C19 1.462(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 
C1 S1 C2 93.68(15) . . ? 
C8 O3 C10 106.9(2) . . ? 
O1 C1 C4 130.9(3) . . ? 
O1 C1 S1 119.5(2) . . ? 
C4 C1 S1 109.5(2) . . ? 
O2 C2 C3 130.4(3) . . ? 
O2 C2 S1 120.5(2) . . ? 
C3 C2 S1 109.1(2) . . ? 
C5 C3 C4 125.7(3) . . ? 
C5 C3 C2 120.4(3) . . ? 
C4 C3 C2 111.6(2) . . ? 
C13 C4 C3 128.2(3) . . ? 
C13 C4 C1 120.6(3) . . ? 
C3 C4 C1 111.0(2) . . ? 
C3 C5 C7 123.3(3) . . ? 
C3 C5 C6 122.2(3) . . ? 
C7 C5 C6 114.3(2) . . ? 
C8 C7 C12 105.6(3) . . ? 
C8 C7 C5 128.9(2) . . ? 
C12 C7 C5 125.5(3) . . ? 
C7 C8 O3 110.8(2) . . ? 
C7 C8 C9 133.2(3) . . ? 
O3 C8 C9 115.9(3) . . ? 
C12 C10 O3 109.2(2) . . ? 
C12 C10 C11 135.2(3) . . ? 
O3 C10 C11 115.5(3) . . ? 
C10 C12 C7 107.4(3) . . ? 
C4 C13 C17 122.4(3) . . ? 
C4 C13 C14 121.9(3) . . ? 
C17 C13 C14 115.7(2) . . ? 
C13 C14 C15 123.9(3) . . ? 
C13 C14 C16 118.3(2) . . ? 
C15 C14 C16 59.1(2) . . ? 
C16 C15 C14 61.0(2) . . ? 
C15 C16 C14 59.9(2) . . ? 
C13 C17 C18 124.1(3) . . ? 
C13 C17 C19 120.1(3) . . ? 
C18 C17 C19 58.1(2) . . ? 
C19 C18 C17 61.2(2) . . ? 
C18 C19 C17 60.7(2) . . ? 
 
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 
 C2 S1 C1 O1 179.1(2) . . . . ? 
 C2 S1 C1 C4 -3.4(2) . . . . ? 
 C1 S1 C2 O2 172.2(2) . . . . ? 
 C1 S1 C2 C3 -10.3(2) . . . . ? 
 O2 C2 C3 C5 35.3(4) . . . . ? 
 S1 C2 C3 C5 -141.9(2) . . . . ? 
 O2 C2 C3 C4 -161.1(3) . . . . ? 
 S1 C2 C3 C4 21.7(3) . . . . ? 
 C5 C3 C4 C13 -47.5(4) . . . . ? 
 C2 C3 C4 C13 149.9(3) . . . . ? 
 C5 C3 C4 C1 137.8(3) . . . . ? 
 C2 C3 C4 C1 -24.8(3) . . . . ? 
 O1 C1 C4 C13 18.4(4) . . . . ? 
 S1 C1 C4 C13 -158.7(2) . . . . ? 
 O1 C1 C4 C3 -166.4(3) . . . . ? 
 S1 C1 C4 C3 16.5(3) . . . . ? 
 C4 C3 C5 C7 -175.2(2) . . . . ? 
 C2 C3 C5 C7 -14.0(4) . . . . ? 
 C4 C3 C5 C6 -0.0(4) . . . . ? 
 C2 C3 C5 C6 161.1(2) . . . . ? 
 C3 C5 C7 C8 -58.9(4) . . . . ? 
 C6 C5 C7 C8 125.6(3) . . . . ? 
 C3 C5 C7 C12 125.2(3) . . . . ? 
 C6 C5 C7 C12 -50.2(4) . . . . ? 
 C12 C7 C8 O3 -1.2(3) . . . . ? 
 C5 C7 C8 O3 -177.7(3) . . . . ? 
 C12 C7 C8 C9 175.0(3) . . . . ? 
 C5 C7 C8 C9 -1.5(5) . . . . ? 
 C10 O3 C8 C7 -0.4(3) . . . . ? 
 C10 O3 C8 C9 -177.3(2) . . . . ? 
 C8 O3 C10 C12 1.9(3) . . . . ? 
 C8 O3 C10 C11 -176.8(2) . . . . ? 
 O3 C10 C12 C7 -2.6(3) . . . . ? 
 C11 C10 C12 C7 175.8(3) . . . . ? 
 C8 C7 C12 C10 2.3(3) . . . . ? 
 C5 C7 C12 C10 179.0(3) . . . . ? 
 C3 C4 C13 C17 166.3(3) . . . . ? 
 C1 C4 C13 C17 -19.4(4) . . . . ? 
 C3 C4 C13 C14 -13.1(4) . . . . ? 
 C1 C4 C13 C14 161.2(2) . . . . ? 
 C4 C13 C14 C15 -34.5(4) . . . . ? 
 C17 C13 C14 C15 146.0(3) . . . . ? 
 C4 C13 C14 C16 -104.6(3) . . . . ? 
 C17 C13 C14 C16 75.9(3) . . . . ? 
 C13 C14 C15 C16 -105.3(3) . . . . ? 
 C16 C14 C15 C16 0.0 . . . . ? 
 C14 C15 C16 C14 0.0 . . . . ? 
 C13 C14 C16 C15 114.6(3) . . . . ? 
 C15 C14 C16 C15 0.0 . . . . ? 
 C4 C13 C17 C18 161.6(3) . . . . ? 
 C14 C13 C17 C18 -18.9(4) . . . . ? 
 C4 C13 C17 C19 -128.5(3) . . . . ? 
 C14 C13 C17 C19 50.9(4) . . . . ? 
 C13 C17 C18 C19 107.0(3) . . . . ? 
 C19 C17 C18 C19 0.0 . . . . ? 
 C17 C18 C19 C17 0.0 . . . . ? 
 C13 C17 C19 C18 -113.8(3) . . . . ? 
 C18 C17 C19 C18 0.0 . . . . ? 
 
_refine_diff_density_max    0.404 
_refine_diff_density_min   -0.333 
_refine_diff_density_rms    0.091