# Supplementary Material (ESI) for Perkin Transactions
# This journal is © The Royal Society of Chemistry 1999
# CCDC Number: 207/366

# Lewis Acid Mediated Elimination and Rearrangement Reactions of
# alpha-chlorosulfides derived from Benzenethio-substituted
# 4,5-Dihydro-3(2H)-Furanones.

# D.G. McCarthy, C.C. Collins, J.P. O'Driscoll & S.E. Lawrence

data_dgm9701 
 
_audit_creation_method            SHELXL 
_chemical_name_systematic 
; 
 ? 
; 
_chemical_name_common             ? 
_chemical_formula_moiety          'C20 H21 Cl O4 S' 
_chemical_formula_structural      ? 
_chemical_formula_analytical      ? 
_chemical_formula_sum             'C20 H21 Cl O4 S' 
_chemical_formula_weight          392.88 
_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' 
 'Cl'  'Cl'   0.1484   0.1585 
 '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/n 
 
loop_ 
 _symmetry_equiv_pos_as_xyz 
 'x, y, z' 
 '-x+1/2, y, -z+1/2' 
 '-x, -y, -z' 
 'x-1/2, -y, z-1/2' 
 
_cell_length_a                    12.291(4) 
_cell_length_b                    11.696(2) 
_cell_length_c                    13.693(3) 
_cell_angle_alpha                 90.000(13) 
_cell_angle_beta                  96.95(2) 
_cell_angle_gamma                 90.00(2) 
_cell_volume                      1954.1(8) 
_cell_formula_units_Z             4 
_cell_measurement_temperature     293(2) 
_cell_measurement_reflns_used     22 
_cell_measurement_theta_min       12.45 
_cell_measurement_theta_max       17.75 
 
_exptl_crystal_description        Needles 
_exptl_crystal_colour             Colourless 
_exptl_crystal_size_max           0.50 
_exptl_crystal_size_mid           0.45 
_exptl_crystal_size_min           0.40 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_diffrn     1.335 
_exptl_crystal_density_method     ? 
_exptl_crystal_F_000              824 
_exptl_absorpt_coefficient_mu     0.324 
_exptl_absorpt_correction_type    none 
_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        'Nonius MACH3' 
_diffrn_measurement_method        'omega/2theta scans' 
_diffrn_standards_number          3 
_diffrn_standards_interval_count  ? 
_diffrn_standards_interval_time   '3600 seconds' 
_diffrn_standards_decay_%         7.6 
_diffrn_reflns_number             7280 
_diffrn_reflns_av_R_equivalents   0.0439 
_diffrn_reflns_av_sigmaI/netI     0.0615 
_diffrn_reflns_limit_h_min        -14 
_diffrn_reflns_limit_h_max        14 
_diffrn_reflns_limit_k_min        -13 
_diffrn_reflns_limit_k_max        13 
_diffrn_reflns_limit_l_min        -1 
_diffrn_reflns_limit_l_max        16 
_diffrn_reflns_theta_min          1.74 
_diffrn_reflns_theta_max          24.96 
_reflns_number_total              3445 
_reflns_number_observed           2362 
_reflns_observed_criterion        >2sigma(I) 
 
_computing_data_collection        'Nonius MACH3' 
_computing_cell_refinement        'Nonius MACH3' 
_computing_data_reduction         'maXus (Gilmore, 1998)'
_computing_structure_solution     'SHELXS-86 (Sheldrick, 1990)' 
_computing_structure_refinement   'SHELXL-93 (Sheldrick, 1993)' 
_computing_molecular_graphics     'PLATON (Spek, 1998)' 
_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^)+(0.0348P)^2^+0.1762P] 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      SHELXL 
_refine_ls_extinction_coef        0.0014(4) 
_refine_ls_extinction_expression 
 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' 
_refine_ls_number_reflns          3445 
_refine_ls_number_parameters      236 
_refine_ls_number_restraints      0 
_refine_ls_R_factor_all           0.0603 
_refine_ls_R_factor_obs           0.0355 
_refine_ls_wR_factor_all          0.0968 
_refine_ls_wR_factor_obs          0.0888 
_refine_ls_goodness_of_fit_all    1.034 
_refine_ls_goodness_of_fit_obs    1.164 
_refine_ls_restrained_S_all       1.034 
_refine_ls_restrained_S_obs       1.164 
_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 
O1 O 0.03372(13) 0.23163(12) 0.38304(11) 0.0554(4) Uani 1 d . . 
C2 C -0.0076(2) 0.3381(2) 0.3387(2) 0.0582(6) Uani 1 d . . 
C3 C -0.0533(2) 0.3052(2) 0.2341(2) 0.0482(5) Uani 1 d . . 
C4 C -0.0343(2) 0.1764(2) 0.2242(2) 0.0446(5) Uani 1 d . . 
C5 C -0.0252(2) 0.1395(2) 0.3340(2) 0.0463(5) Uani 1 d . . 
H5 H -0.0989(2) 0.1371(2) 0.3544(2) 0.056 Uiso 1 calc R . 
O6 O -0.09937(14) 0.36704(13) 0.17261(13) 0.0639(5) Uani 1 d . . 
Cl7 Cl -0.14454(5) 0.10841(5) 0.14968(4) 0.0589(2) Uani 1 d . . 
S8 S 0.09778(5) 0.15680(5) 0.17819(4) 0.0569(2) Uani 1 d . . 
C9 C 0.0879(3) 0.4207(2) 0.3421(2) 0.0845(9) Uani 1 d . . 
H9A H 0.1137(3) 0.4387(2) 0.4094(2) 0.127 Uiso 1 calc R . 
H9B H 0.0644(3) 0.4896(2) 0.3076(2) 0.127 Uiso 1 calc R . 
H9C H 0.1461(3) 0.3863(2) 0.3116(2) 0.127 Uiso 1 calc R . 
C10 C -0.1016(3) 0.3844(2) 0.3911(2) 0.0824(9) Uani 1 d . . 
H10A H -0.1598(3) 0.3292(2) 0.3869(2) 0.124 Uiso 1 calc R . 
H10B H -0.1283(3) 0.4544(2) 0.3603(2) 0.124 Uiso 1 calc R . 
H10C H -0.0755(3) 0.3987(2) 0.4590(2) 0.124 Uiso 1 calc R . 
C11 C 0.0310(2) 0.0267(2) 0.35956(15) 0.0427(5) Uani 1 d . . 
C12 C 0.1431(2) 0.0161(2) 0.3748(2) 0.0533(6) Uani 1 d . . 
H12 H 0.1868(2) 0.0812(2) 0.3769(2) 0.064 Uiso 1 calc R . 
C13 C 0.1919(2) -0.0915(2) 0.3870(2) 0.0542(6) Uani 1 d . . 
H13 H 0.2679(2) -0.0980(2) 0.3962(2) 0.065 Uiso 1 calc R . 
C14 C 0.1273(2) -0.1884(2) 0.3855(2) 0.0477(5) Uani 1 d . . 
C15 C 0.0134(2) -0.1776(2) 0.3763(2) 0.0431(5) Uani 1 d . . 
C16 C -0.0341(2) -0.0705(2) 0.36350(15) 0.0428(5) Uani 1 d . . 
H16 H -0.1099(2) -0.0633(2) 0.35750(15) 0.051 Uiso 1 calc R . 
O17 O 0.16601(13) -0.29872(13) 0.39069(14) 0.0624(5) Uani 1 d . . 
C18 C 0.2819(2) -0.3145(2) 0.3975(3) 0.0800(8) Uani 1 d . . 
H18A H 0.2985(2) -0.3947(2) 0.4006(3) 0.120 Uiso 1 calc R . 
H18B H 0.3165(2) -0.2775(2) 0.4557(3) 0.120 Uiso 1 calc R . 
H18C H 0.3087(2) -0.2818(2) 0.3407(3) 0.120 Uiso 1 calc R . 
O19 O -0.04416(13) -0.27816(12) 0.37866(13) 0.0564(4) Uani 1 d . . 
C20 C -0.1580(2) -0.2701(2) 0.3862(2) 0.0658(7) Uani 1 d . . 
H20A H -0.1888(2) -0.3455(2) 0.3872(2) 0.099 Uiso 1 calc R . 
H20B H -0.1935(2) -0.2286(2) 0.3307(2) 0.099 Uiso 1 calc R . 
H20C H -0.1689(2) -0.2307(2) 0.4457(2) 0.099 Uiso 1 calc R . 
C21 C 0.0798(2) 0.2265(2) 0.0612(2) 0.0479(5) Uani 1 d . . 
C22 C 0.0556(2) 0.1619(2) -0.0220(2) 0.0645(7) Uani 1 d . . 
H22 H 0.0437(2) 0.0838(2) -0.0167(2) 0.077 Uiso 1 calc R . 
C23 C 0.0490(2) 0.2121(3) -0.1133(2) 0.0788(8) Uani 1 d . . 
H23 H 0.0330(2) 0.1674(3) -0.1693(2) 0.095 Uiso 1 calc R . 
C24 C 0.0656(2) 0.3274(3) -0.1227(2) 0.0746(8) Uani 1 d . . 
H24 H 0.0592(2) 0.3612(3) -0.1846(2) 0.090 Uiso 1 calc R . 
C25 C 0.0917(2) 0.3914(2) -0.0403(2) 0.0708(7) Uani 1 d . . 
H25 H 0.1043(2) 0.4694(2) -0.0462(2) 0.085 Uiso 1 calc R . 
C26 C 0.0996(2) 0.3424(2) 0.0523(2) 0.0611(6) Uani 1 d . . 
H26 H 0.1182(2) 0.3869(2) 0.1081(2) 0.073 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 
O1 0.0798(11) 0.0408(8) 0.0438(9) -0.0004(7) -0.0002(8) 0.0004(7) 
C2 0.084(2) 0.0395(12) 0.0512(14) 0.0006(11) 0.0072(13) 0.0030(12) 
C3 0.0549(13) 0.0437(11) 0.0479(13) 0.0062(11) 0.0136(11) 0.0056(10) 
C4 0.0485(12) 0.0442(11) 0.0414(12) 0.0007(10) 0.0066(10) 0.0029(9) 
C5 0.0532(12) 0.0448(12) 0.0413(11) 0.0033(10) 0.0083(10) 0.0007(9) 
O6 0.0814(12) 0.0512(9) 0.0593(10) 0.0130(8) 0.0095(9) 0.0142(8) 
Cl7 0.0603(4) 0.0620(4) 0.0526(3) -0.0045(3) -0.0001(3) -0.0018(3) 
S8 0.0544(3) 0.0665(4) 0.0520(3) 0.0155(3) 0.0157(3) 0.0146(3) 
C9 0.114(2) 0.0524(15) 0.082(2) 0.0014(15) -0.008(2) -0.0190(15) 
C10 0.123(2) 0.063(2) 0.064(2) -0.0059(14) 0.024(2) 0.025(2) 
C11 0.0532(12) 0.0406(11) 0.0349(11) 0.0055(9) 0.0076(9) 0.0008(9) 
C12 0.0529(13) 0.0470(12) 0.0586(14) 0.0114(11) 0.0017(11) -0.0076(10) 
C13 0.0461(12) 0.0549(14) 0.0606(15) 0.0151(12) 0.0029(11) -0.0008(10) 
C14 0.0517(13) 0.0452(12) 0.0462(12) 0.0052(10) 0.0055(10) 0.0035(10) 
C15 0.0524(12) 0.0412(11) 0.0357(11) 0.0026(9) 0.0058(9) -0.0045(9) 
C16 0.0455(12) 0.0486(12) 0.0346(11) 0.0025(9) 0.0067(9) 0.0010(9) 
O17 0.0603(10) 0.0466(9) 0.0800(12) 0.0096(8) 0.0076(9) 0.0097(7) 
C18 0.064(2) 0.067(2) 0.107(2) 0.007(2) 0.002(2) 0.0202(13) 
O19 0.0559(9) 0.0439(8) 0.0696(11) 0.0029(8) 0.0090(8) -0.0076(7) 
C20 0.056(2) 0.0627(15) 0.078(2) 0.0057(14) 0.0055(13) -0.0153(12) 
C21 0.0496(13) 0.0500(12) 0.0465(13) 0.0051(11) 0.0159(10) 0.0066(10) 
C22 0.083(2) 0.0566(14) 0.058(2) -0.0061(13) 0.0231(13) -0.0037(13) 
C23 0.097(2) 0.096(2) 0.0465(15) -0.013(2) 0.0190(15) 0.001(2) 
C24 0.074(2) 0.101(2) 0.053(2) 0.027(2) 0.0220(14) 0.024(2) 
C25 0.086(2) 0.0615(15) 0.070(2) 0.0186(15) 0.033(2) 0.0078(14) 
C26 0.074(2) 0.0549(14) 0.0570(15) 0.0005(12) 0.0184(13) -0.0033(12) 
 
_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 C5 1.421(3) . ? 
O1 C2 1.450(3) . ? 
C2 C9 1.516(4) . ? 
C2 C3 1.523(3) . ? 
C2 C10 1.531(4) . ? 
C3 O6 1.199(3) . ? 
C3 C4 1.533(3) . ? 
C4 C5 1.556(3) . ? 
C4 Cl7 1.782(2) . ? 
C4 S8 1.825(2) . ? 
C5 C11 1.510(3) . ? 
C5 H5 0.98 . ? 
S8 C21 1.787(2) . ? 
C9 H9A 0.96 . ? 
C9 H9B 0.96 . ? 
C9 H9C 0.96 . ? 
C10 H10A 0.96 . ? 
C10 H10B 0.96 . ? 
C10 H10C 0.96 . ? 
C11 C12 1.374(3) . ? 
C11 C16 1.394(3) . ? 
C12 C13 1.396(3) . ? 
C12 H12 0.93 . ? 
C13 C14 1.383(3) . ? 
C13 H13 0.93 . ? 
C14 O17 1.374(3) . ? 
C14 C15 1.396(3) . ? 
C15 O19 1.375(2) . ? 
C15 C16 1.383(3) . ? 
C16 H16 0.93 . ? 
O17 C18 1.428(3) . ? 
C18 H18A 0.96 . ? 
C18 H18B 0.96 . ? 
C18 H18C 0.96 . ? 
O19 C20 1.419(3) . ? 
C20 H20A 0.96 . ? 
C20 H20B 0.96 . ? 
C20 H20C 0.96 . ? 
C21 C22 1.369(3) . ? 
C21 C26 1.385(3) . ? 
C22 C23 1.374(4) . ? 
C22 H22 0.93 . ? 
C23 C24 1.372(4) . ? 
C23 H23 0.93 . ? 
C24 C25 1.361(4) . ? 
C24 H24 0.93 . ? 
C25 C26 1.384(4) . ? 
C25 H25 0.93 . ? 
C26 H26 0.93 . ? 
 
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 
C5 O1 C2 108.7(2) . . ? 
O1 C2 C9 107.7(2) . . ? 
O1 C2 C3 104.3(2) . . ? 
C9 C2 C3 112.7(2) . . ? 
O1 C2 C10 110.7(2) . . ? 
C9 C2 C10 112.6(2) . . ? 
C3 C2 C10 108.5(2) . . ? 
O6 C3 C2 126.7(2) . . ? 
O6 C3 C4 126.5(2) . . ? 
C2 C3 C4 106.8(2) . . ? 
C3 C4 C5 100.4(2) . . ? 
C3 C4 Cl7 112.1(2) . . ? 
C5 C4 Cl7 112.96(15) . . ? 
C3 C4 S8 107.78(14) . . ? 
C5 C4 S8 109.63(15) . . ? 
Cl7 C4 S8 113.14(11) . . ? 
O1 C5 C11 111.1(2) . . ? 
O1 C5 C4 102.6(2) . . ? 
C11 C5 C4 116.3(2) . . ? 
O1 C5 H5 108.82(11) . . ? 
C11 C5 H5 108.82(11) . . ? 
C4 C5 H5 108.82(11) . . ? 
C21 S8 C4 103.48(10) . . ? 
C2 C9 H9A 109.5(2) . . ? 
C2 C9 H9B 109.47(14) . . ? 
H9A C9 H9B 109.5 . . ? 
C2 C9 H9C 109.47(15) . . ? 
H9A C9 H9C 109.5 . . ? 
H9B C9 H9C 109.5 . . ? 
C2 C10 H10A 109.47(15) . . ? 
C2 C10 H10B 109.47(14) . . ? 
H10A C10 H10B 109.5 . . ? 
C2 C10 H10C 109.5(2) . . ? 
H10A C10 H10C 109.5 . . ? 
H10B C10 H10C 109.5 . . ? 
C12 C11 C16 119.3(2) . . ? 
C12 C11 C5 122.4(2) . . ? 
C16 C11 C5 118.2(2) . . ? 
C11 C12 C13 120.5(2) . . ? 
C11 C12 H12 119.75(13) . . ? 
C13 C12 H12 119.75(13) . . ? 
C14 C13 C12 120.0(2) . . ? 
C14 C13 H13 120.01(13) . . ? 
C12 C13 H13 120.01(13) . . ? 
O17 C14 C13 125.1(2) . . ? 
O17 C14 C15 115.3(2) . . ? 
C13 C14 C15 119.7(2) . . ? 
O19 C15 C16 124.5(2) . . ? 
O19 C15 C14 115.7(2) . . ? 
C16 C15 C14 119.8(2) . . ? 
C15 C16 C11 120.5(2) . . ? 
C15 C16 H16 119.73(12) . . ? 
C11 C16 H16 119.73(12) . . ? 
C14 O17 C18 117.4(2) . . ? 
O17 C18 H18A 109.47(13) . . ? 
O17 C18 H18B 109.5(2) . . ? 
H18A C18 H18B 109.5 . . ? 
O17 C18 H18C 109.5(2) . . ? 
H18A C18 H18C 109.5 . . ? 
H18B C18 H18C 109.5 . . ? 
C15 O19 C20 117.4(2) . . ? 
O19 C20 H20A 109.47(12) . . ? 
O19 C20 H20B 109.47(13) . . ? 
H20A C20 H20B 109.5 . . ? 
O19 C20 H20C 109.47(13) . . ? 
H20A C20 H20C 109.5 . . ? 
H20B C20 H20C 109.5 . . ? 
C22 C21 C26 119.3(2) . . ? 
C22 C21 S8 119.0(2) . . ? 
C26 C21 S8 121.4(2) . . ? 
C21 C22 C23 120.3(2) . . ? 
C21 C22 H22 119.87(14) . . ? 
C23 C22 H22 119.9(2) . . ? 
C24 C23 C22 120.8(3) . . ? 
C24 C23 H23 119.6(2) . . ? 
C22 C23 H23 119.6(2) . . ? 
C25 C24 C23 119.0(3) . . ? 
C25 C24 H24 120.5(2) . . ? 
C23 C24 H24 120.5(2) . . ? 
C24 C25 C26 121.0(2) . . ? 
C24 C25 H25 119.5(2) . . ? 
C26 C25 H25 119.5(2) . . ? 
C25 C26 C21 119.5(3) . . ? 
C25 C26 H26 120.2(2) . . ? 
C21 C26 H26 120.2(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 
 C5 O1 C2 C9 -146.1(2) . . . . ? 
 C5 O1 C2 C3 -26.1(2) . . . . ? 
 C5 O1 C2 C10 90.4(2) . . . . ? 
 O1 C2 C3 O6 177.0(2) . . . . ? 
 C9 C2 C3 O6 -66.5(3) . . . . ? 
 C10 C2 C3 O6 59.0(3) . . . . ? 
 O1 C2 C3 C4 -0.2(2) . . . . ? 
 C9 C2 C3 C4 116.3(2) . . . . ? 
 C10 C2 C3 C4 -118.2(2) . . . . ? 
 O6 C3 C4 C5 -154.1(2) . . . . ? 
 C2 C3 C4 C5 23.1(2) . . . . ? 
 O6 C3 C4 Cl7 -33.9(3) . . . . ? 
 C2 C3 C4 Cl7 143.3(2) . . . . ? 
 O6 C3 C4 S8 91.2(2) . . . . ? 
 C2 C3 C4 S8 -91.6(2) . . . . ? 
 C2 O1 C5 C11 166.3(2) . . . . ? 
 C2 O1 C5 C4 41.3(2) . . . . ? 
 C3 C4 C5 O1 -38.4(2) . . . . ? 
 Cl7 C4 C5 O1 -157.92(13) . . . . ? 
 S8 C4 C5 O1 74.9(2) . . . . ? 
 C3 C4 C5 C11 -159.9(2) . . . . ? 
 Cl7 C4 C5 C11 80.5(2) . . . . ? 
 S8 C4 C5 C11 -46.6(2) . . . . ? 
 C3 C4 S8 C21 -61.4(2) . . . . ? 
 C5 C4 S8 C21 -169.82(14) . . . . ? 
 Cl7 C4 S8 C21 63.12(14) . . . . ? 
 O1 C5 C11 C12 -35.5(3) . . . . ? 
 C4 C5 C11 C12 81.4(3) . . . . ? 
 O1 C5 C11 C16 147.3(2) . . . . ? 
 C4 C5 C11 C16 -95.8(2) . . . . ? 
 C16 C11 C12 C13 4.6(3) . . . . ? 
 C5 C11 C12 C13 -172.6(2) . . . . ? 
 C11 C12 C13 C14 -1.1(4) . . . . ? 
 C12 C13 C14 O17 175.8(2) . . . . ? 
 C12 C13 C14 C15 -3.0(4) . . . . ? 
 O17 C14 C15 O19 3.2(3) . . . . ? 
 C13 C14 C15 O19 -177.9(2) . . . . ? 
 O17 C14 C15 C16 -175.5(2) . . . . ? 
 C13 C14 C15 C16 3.4(3) . . . . ? 
 O19 C15 C16 C11 -178.4(2) . . . . ? 
 C14 C15 C16 C11 0.2(3) . . . . ? 
 C12 C11 C16 C15 -4.2(3) . . . . ? 
 C5 C11 C16 C15 173.2(2) . . . . ? 
 C13 C14 O17 C18 -0.5(4) . . . . ? 
 C15 C14 O17 C18 178.3(2) . . . . ? 
 C16 C15 O19 C20 -11.7(3) . . . . ? 
 C14 C15 O19 C20 169.7(2) . . . . ? 
 C4 S8 C21 C22 -98.9(2) . . . . ? 
 C4 S8 C21 C26 87.2(2) . . . . ? 
 C26 C21 C22 C23 -1.3(4) . . . . ? 
 S8 C21 C22 C23 -175.4(2) . . . . ? 
 C21 C22 C23 C24 -0.4(4) . . . . ? 
 C22 C23 C24 C25 1.7(5) . . . . ? 
 C23 C24 C25 C26 -1.1(4) . . . . ? 
 C24 C25 C26 C21 -0.6(4) . . . . ? 
 C22 C21 C26 C25 1.9(4) . . . . ? 
 S8 C21 C26 C25 175.8(2) . . . . ? 
 
_refine_diff_density_max    0.229 
_refine_diff_density_min   -0.186 
_refine_diff_density_rms    0.035 

#===END

 
data_dgm9702 
 
_audit_creation_method            SHELXL-97 
_chemical_name_systematic 
; 
 ? 
; 
_chemical_name_common             ? 
_chemical_formula_moiety          'C20 H20 O4 S' 
_chemical_formula_sum 
 'C20 H20 O4 S' 
_chemical_formula_weight          356.42 
 
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    P21/n 
 
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                    5.9199(19) 
_cell_length_b                    16.419(5) 
_cell_length_c                    18.436(5) 
_cell_angle_alpha                 90.00 
_cell_angle_beta                  93.33(3) 
_cell_angle_gamma                 90.00 
_cell_volume                      1788.9(9) 
_cell_formula_units_Z             4 
_cell_measurement_temperature     293(2) 
_cell_measurement_reflns_used     22 
_cell_measurement_theta_min       11.65 
_cell_measurement_theta_max       14.85 
 
_exptl_crystal_description        blocks 
_exptl_crystal_colour             colourless 
_exptl_crystal_size_max           0.70 
_exptl_crystal_size_mid           0.50 
_exptl_crystal_size_min           0.30 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_diffrn     1.323 
_exptl_crystal_density_method     'not measured' 
_exptl_crystal_F_000              752 
_exptl_absorpt_coefficient_mu     0.202 
_exptl_absorpt_correction_type    none 
_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_type   'Nonius MACH3' 
_diffrn_measurement_method        'omega/2theta scans' 
_diffrn_detector_area_resol_mean  ? 
_diffrn_standards_number          3 
_diffrn_standards_interval_count  ? 
_diffrn_standards_interval_time   '3600 seconds' 
_diffrn_standards_decay_%         1.8 
_diffrn_reflns_number             6389 
_diffrn_reflns_av_R_equivalents   0.0269 
_diffrn_reflns_av_sigmaI/netI     0.1610 
_diffrn_reflns_limit_h_min        -2 
_diffrn_reflns_limit_h_max        7 
_diffrn_reflns_limit_k_min        -15 
_diffrn_reflns_limit_k_max        21 
_diffrn_reflns_limit_l_min        -23 
_diffrn_reflns_limit_l_max        20 
_diffrn_reflns_theta_min          2.21 
_diffrn_reflns_theta_max          27.51 
_reflns_number_total              4044 
_reflns_number_gt                 1665 
_reflns_threshold_expression      >2sigma(I) 
 
_computing_data_collection        'Nonius MACH3' 
_computing_cell_refinement        'Nonius MACH3' 
_computing_data_reduction         'maXus (Gilmore, 1998)'
_computing_structure_solution     'SHELXS-97 (Sheldrick, 1990)' 
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 1997)' 
_computing_molecular_graphics     'PLATON (Spek, 1998) '
_computing_publication_material   ? 
 
_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 w=1/[\s^2^(Fo^2^)+(0.0500P)^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     mixed 
_refine_ls_extinction_method      SHELXL 
_refine_ls_extinction_coef        0.0029(10) 
_refine_ls_extinction_expression 
 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' 
_refine_ls_number_reflns          4044 
_refine_ls_number_parameters      227 
_refine_ls_number_restraints      0 
_refine_ls_R_factor_all           0.1625 
_refine_ls_R_factor_gt            0.0605 
_refine_ls_wR_factor_ref          0.1221 
_refine_ls_wR_factor_gt           0.1038 
_refine_ls_goodness_of_fit_ref    0.892 
_refine_ls_restrained_S_all       0.892 
_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_calc_flag 
 _atom_site_refinement_flags 
 _atom_site_disorder_assembly 
 _atom_site_disorder_group 
O1 O 0.7690(3) 0.39643(12) -0.02342(10) 0.0484(6) Uani 1 d . . . 
C2 C 0.7668(5) 0.43267(17) -0.09639(14) 0.0380(8) Uani 1 d . . . 
C3 C 0.6227(5) 0.37449(17) -0.14307(16) 0.0420(8) Uani 1 d . . . 
C4 C 0.5402(5) 0.31164(17) -0.09478(15) 0.0346(7) Uani 1 d . . . 
C5 C 0.6382(5) 0.32960(19) -0.02929(16) 0.0454(8) Uani 1 d . . . 
H5 H 0.6163 0.2968 0.0108 0.055 Uiso 1 calc R . . 
O6 O 0.5887(4) 0.38297(13) -0.20817(11) 0.0679(8) Uani 1 d . . . 
C7 C 1.0083(5) 0.4370(2) -0.11806(18) 0.0553(9) Uani 1 d . . . 
H7A H 1.0911 0.4752 -0.0873 0.083 Uiso 1 calc R . . 
H7B H 1.0107 0.4543 -0.1677 0.083 Uiso 1 calc R . . 
H7C H 1.0769 0.3841 -0.1129 0.083 Uiso 1 calc R . . 
C8 C 0.6555(6) 0.51591(17) -0.09332(17) 0.0517(9) Uani 1 d . . . 
H8A H 0.5028 0.5098 -0.0793 0.078 Uiso 1 calc R . . 
H8B H 0.6547 0.5411 -0.1403 0.078 Uiso 1 calc R . . 
H8C H 0.7387 0.5494 -0.0584 0.078 Uiso 1 calc R . . 
C9 C 0.3808(5) 0.24653(17) -0.11801(14) 0.0360(7) Uani 1 d . . . 
C10 C 0.2166(5) 0.21292(17) -0.07486(15) 0.0376(8) Uani 1 d . . . 
C11 C 0.0599(5) 0.15649(17) -0.10554(16) 0.0445(8) Uani 1 d . . . 
H11 H -0.0503 0.1356 -0.0768 0.053 Uiso 1 calc R . . 
C12 C 0.0636(5) 0.13117(18) -0.17624(16) 0.0434(8) Uani 1 d . . . 
C13 C 0.2322(5) 0.16251(18) -0.21904(16) 0.0406(8) Uani 1 d . . . 
C14 C 0.3831(5) 0.21878(17) -0.19027(15) 0.0394(8) Uani 1 d . . . 
H14 H 0.4916 0.2396 -0.2197 0.047 Uiso 1 calc R . . 
O15 O -0.0816(4) 0.07725(13) -0.20979(11) 0.0583(6) Uani 1 d . . . 
C16 C -0.2420(6) 0.0378(2) -0.16738(19) 0.0649(11) Uani 1 d . . . 
H16A H -0.3335 0.0017 -0.1977 0.097 Uiso 1 calc R . . 
H16B H -0.3369 0.0778 -0.1465 0.097 Uiso 1 calc R . . 
H16C H -0.1641 0.0071 -0.1293 0.097 Uiso 1 calc R . . 
O17 O 0.2292(4) 0.13305(13) -0.28830(11) 0.0569(6) Uani 1 d . . . 
C18 C 0.4038(6) 0.1598(2) -0.33269(16) 0.0572(9) Uani 1 d . . . 
H18A H 0.3835 0.1352 -0.3798 0.086 Uiso 1 calc R . . 
H18B H 0.5483 0.1443 -0.3106 0.086 Uiso 1 calc R . . 
H18C H 0.3972 0.2180 -0.3375 0.086 Uiso 1 calc R . . 
S19 S 0.18655(14) 0.24081(5) 0.01690(4) 0.0472(3) Uani 1 d . . . 
C20 C 0.3914(5) 0.17901(17) 0.06493(15) 0.0398(8) Uani 1 d . . . 
C21 C 0.5178(6) 0.1195(2) 0.03347(18) 0.0577(10) Uani 1 d . . . 
H21 H 0.4962 0.1085 -0.0159 0.069 Uiso 1 calc R . . 
C22 C 0.6771(7) 0.0760(2) 0.0757(2) 0.0742(12) Uani 1 d . . . 
H22 H 0.7624 0.0362 0.0541 0.089 Uiso 1 calc R . . 
C23 C 0.7114(7) 0.0904(2) 0.1485(2) 0.0651(10) Uani 1 d . . . 
H23 H 0.8200 0.0611 0.1761 0.078 Uiso 1 calc R . . 
C24 C 0.5848(7) 0.1481(2) 0.18008(19) 0.0611(10) Uani 1 d . . . 
H24 H 0.6048 0.1576 0.2298 0.073 Uiso 1 calc R . . 
C25 C 0.4268(6) 0.1927(2) 0.13886(17) 0.0542(9) Uani 1 d . . . 
H25 H 0.3429 0.2326 0.1610 0.065 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 
O1 0.0557(15) 0.0434(13) 0.0446(12) 0.0009(10) -0.0100(11) -0.0148(12) 
C2 0.0420(19) 0.0373(18) 0.0348(17) 0.0008(14) 0.0028(15) -0.0016(16) 
C3 0.041(2) 0.0415(19) 0.0430(19) -0.0005(16) -0.0018(15) -0.0002(16) 
C4 0.0338(18) 0.0340(17) 0.0356(17) -0.0030(14) -0.0017(15) 0.0011(14) 
C5 0.052(2) 0.0385(19) 0.0448(19) 0.0077(15) -0.0029(16) -0.0046(17) 
O6 0.099(2) 0.0634(16) 0.0393(14) 0.0075(11) -0.0092(13) -0.0324(15) 
C7 0.042(2) 0.054(2) 0.071(2) -0.0012(18) 0.0013(18) -0.0044(18) 
C8 0.052(2) 0.043(2) 0.060(2) -0.0009(16) 0.0048(17) 0.0017(17) 
C9 0.0344(16) 0.0306(17) 0.0421(17) 0.0016(15) -0.0064(14) 0.0028(16) 
C10 0.0399(18) 0.0365(17) 0.0362(17) 0.0000(13) 0.0006(15) 0.0016(15) 
C11 0.0389(19) 0.0392(18) 0.055(2) 0.0104(16) 0.0031(16) -0.0016(16) 
C12 0.046(2) 0.0374(18) 0.0453(19) -0.0055(15) -0.0115(17) -0.0040(17) 
C13 0.047(2) 0.0360(17) 0.0386(18) -0.0039(15) 0.0003(15) -0.0030(16) 
C14 0.0453(19) 0.0343(17) 0.0389(18) 0.0013(14) 0.0058(15) -0.0042(16) 
O15 0.0590(16) 0.0569(15) 0.0585(14) -0.0078(12) 0.0004(13) -0.0244(13) 
C16 0.055(2) 0.056(2) 0.084(3) -0.006(2) 0.005(2) -0.020(2) 
O17 0.0694(17) 0.0520(14) 0.0496(14) -0.0119(11) 0.0062(12) -0.0184(13) 
C18 0.073(3) 0.060(2) 0.0389(19) -0.0077(17) 0.0046(19) -0.003(2) 
S19 0.0487(5) 0.0514(6) 0.0417(4) -0.0015(4) 0.0059(4) 0.0073(5) 
C20 0.0421(19) 0.0379(18) 0.0392(18) 0.0049(14) 0.0015(15) -0.0064(16) 
C21 0.072(3) 0.055(2) 0.047(2) 0.0017(17) 0.0019(19) 0.025(2) 
C22 0.084(3) 0.071(3) 0.068(3) 0.002(2) 0.008(2) 0.031(3) 
C23 0.067(3) 0.060(3) 0.066(3) 0.017(2) -0.011(2) -0.001(2) 
C24 0.075(3) 0.059(2) 0.047(2) 0.0078(19) -0.010(2) -0.013(2) 
C25 0.065(2) 0.053(2) 0.045(2) 0.0022(17) 0.0070(18) -0.0013(19) 
 
_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 C5 1.344(3) . ? 
O1 C2 1.470(3) . ? 
C2 C7 1.509(4) . ? 
C2 C8 1.520(4) . ? 
C2 C3 1.515(4) . ? 
C3 O6 1.213(3) . ? 
C3 C4 1.465(4) . ? 
C4 C5 1.342(4) . ? 
C4 C9 1.473(4) . ? 
C9 C10 1.404(4) . ? 
C9 C14 1.409(4) . ? 
C10 C11 1.406(4) . ? 
C10 S19 1.772(3) . ? 
C11 C12 1.369(4) . ? 
C12 O15 1.358(3) . ? 
C12 C13 1.406(4) . ? 
C13 O17 1.364(3) . ? 
C13 C14 1.370(4) . ? 
O15 C16 1.421(4) . ? 
O17 C18 1.425(4) . ? 
S19 C20 1.778(3) . ? 
C20 C21 1.379(4) . ? 
C20 C25 1.385(4) . ? 
C21 C22 1.386(4) . ? 
C22 C23 1.365(5) . ? 
C23 C24 1.360(5) . ? 
C24 C25 1.381(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 
C5 O1 C2 106.4(2) . . ? 
O1 C2 C7 107.6(2) . . ? 
O1 C2 C8 108.1(2) . . ? 
C7 C2 C8 112.8(3) . . ? 
O1 C2 C3 103.9(2) . . ? 
C7 C2 C3 113.0(2) . . ? 
C8 C2 C3 110.9(2) . . ? 
O6 C3 C4 129.8(3) . . ? 
O6 C3 C2 123.0(3) . . ? 
C4 C3 C2 107.2(2) . . ? 
C5 C4 C3 104.5(3) . . ? 
C5 C4 C9 131.1(3) . . ? 
C3 C4 C9 124.4(2) . . ? 
C4 C5 O1 118.0(3) . . ? 
C10 C9 C14 117.0(3) . . ? 
C10 C9 C4 125.0(3) . . ? 
C14 C9 C4 117.9(3) . . ? 
C9 C10 C11 119.6(3) . . ? 
C9 C10 S19 123.4(2) . . ? 
C11 C10 S19 117.0(2) . . ? 
C12 C11 C10 122.4(3) . . ? 
O15 C12 C11 125.9(3) . . ? 
O15 C12 C13 115.8(3) . . ? 
C11 C12 C13 118.3(3) . . ? 
O17 C13 C14 125.1(3) . . ? 
O17 C13 C12 115.1(3) . . ? 
C14 C13 C12 119.8(3) . . ? 
C13 C14 C9 122.9(3) . . ? 
C12 O15 C16 118.2(3) . . ? 
C13 O17 C18 117.2(2) . . ? 
C10 S19 C20 102.98(14) . . ? 
C21 C20 C25 118.3(3) . . ? 
C21 C20 S19 124.5(2) . . ? 
C25 C20 S19 117.2(2) . . ? 
C20 C21 C22 119.8(3) . . ? 
C23 C22 C21 121.4(4) . . ? 
C24 C23 C22 119.1(4) . . ? 
C23 C24 C25 120.4(3) . . ? 
C24 C25 C20 120.9(3) . . ? 
 
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 
C5 O1 C2 C7 -121.8(3) . . . . ? 
C5 O1 C2 C8 116.1(3) . . . . ? 
C5 O1 C2 C3 -1.8(3) . . . . ? 
O1 C2 C3 O6 -177.3(3) . . . . ? 
C7 C2 C3 O6 -61.0(4) . . . . ? 
C8 C2 C3 O6 66.8(4) . . . . ? 
O1 C2 C3 C4 3.2(3) . . . . ? 
C7 C2 C3 C4 119.5(3) . . . . ? 
C8 C2 C3 C4 -112.7(3) . . . . ? 
O6 C3 C4 C5 177.2(3) . . . . ? 
C2 C3 C4 C5 -3.4(3) . . . . ? 
O6 C3 C4 C9 -4.0(5) . . . . ? 
C2 C3 C4 C9 175.5(3) . . . . ? 
C3 C4 C5 O1 2.4(4) . . . . ? 
C9 C4 C5 O1 -176.3(3) . . . . ? 
C2 O1 C5 C4 -0.3(4) . . . . ? 
C5 C4 C9 C10 32.1(5) . . . . ? 
C3 C4 C9 C10 -146.4(3) . . . . ? 
C5 C4 C9 C14 -151.8(3) . . . . ? 
C3 C4 C9 C14 29.6(4) . . . . ? 
C14 C9 C10 C11 -2.2(4) . . . . ? 
C4 C9 C10 C11 173.9(3) . . . . ? 
C14 C9 C10 S19 -179.5(2) . . . . ? 
C4 C9 C10 S19 -3.4(4) . . . . ? 
C9 C10 C11 C12 1.5(4) . . . . ? 
S19 C10 C11 C12 179.0(2) . . . . ? 
C10 C11 C12 O15 -179.8(3) . . . . ? 
C10 C11 C12 C13 0.6(4) . . . . ? 
O15 C12 C13 O17 -1.2(4) . . . . ? 
C11 C12 C13 O17 178.4(3) . . . . ? 
O15 C12 C13 C14 178.5(3) . . . . ? 
C11 C12 C13 C14 -1.9(4) . . . . ? 
O17 C13 C14 C9 -179.2(3) . . . . ? 
C12 C13 C14 C9 1.2(4) . . . . ? 
C10 C9 C14 C13 0.9(4) . . . . ? 
C4 C9 C14 C13 -175.5(3) . . . . ? 
C11 C12 O15 C16 -5.4(4) . . . . ? 
C13 C12 O15 C16 174.2(3) . . . . ? 
C14 C13 O17 C18 3.5(4) . . . . ? 
C12 C13 O17 C18 -176.9(3) . . . . ? 
C9 C10 S19 C20 -83.5(3) . . . . ? 
C11 C10 S19 C20 99.1(2) . . . . ? 
C10 S19 C20 C21 -5.8(3) . . . . ? 
C10 S19 C20 C25 173.5(2) . . . . ? 
C25 C20 C21 C22 -0.8(5) . . . . ? 
S19 C20 C21 C22 178.5(3) . . . . ? 
C20 C21 C22 C23 0.4(6) . . . . ? 
C21 C22 C23 C24 0.6(6) . . . . ? 
C22 C23 C24 C25 -1.3(6) . . . . ? 
C23 C24 C25 C20 0.9(5) . . . . ? 
C21 C20 C25 C24 0.1(5) . . . . ? 
S19 C20 C25 C24 -179.2(3) . . . . ? 
 
_diffrn_measured_fraction_theta_max    0.978 
_diffrn_reflns_theta_full              27.51 
_diffrn_measured_fraction_theta_full   0.978 
_refine_diff_density_max    0.192 
_refine_diff_density_min   -0.199 
_refine_diff_density_rms    0.049