# Copyright The Royal Society of Chemistry, 1999
# CCDC Number: 182/1252 
data_et18 
 
_audit_creation_method            SHELXL-97 
_chemical_name_systematic 
; 
 ? 
; 
_chemical_name_common             ? 
_chemical_melting_point           ? 
_chemical_formula_moiety          ? 
_chemical_formula_sum 
 'C20 H16 O2 S8' 
_chemical_formula_weight          544.81 
 
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)   '
 
loop_ 
 _symmetry_equiv_pos_as_xyz 
 'x, y, z' 
 '-x, y+1/2, -z' 
 
_cell_length_a                    8.4863(13) 
_cell_length_b                    8.7703(14) 
_cell_length_c                    15.430(3) 
_cell_angle_alpha                 90.00 
_cell_angle_beta                  98.740(3) 
_cell_angle_gamma                 90.00 
_cell_volume                      1135.0(3) 
_cell_formula_units_Z             2 
_cell_measurement_temperature     298(2) 
_cell_measurement_reflns_used     ? 
_cell_measurement_theta_min       ? 
_cell_measurement_theta_max       ? 
 
_exptl_crystal_description        'Needle' 
_exptl_crystal_colour             'Green' 
_exptl_crystal_size_max           0.4 
_exptl_crystal_size_mid           0.15 
_exptl_crystal_size_min           0.15 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_diffrn     1.594 
_exptl_crystal_density_method     'not measured' 
_exptl_crystal_F_000              560 
_exptl_absorpt_coefficient_mu     0.804 
_exptl_absorpt_correction_type    ' Bruker SADABS' 
_exptl_absorpt_correction_T_min   0.825 
_exptl_absorpt_correction_T_max   1 
_exptl_absorpt_process_details    
'Absorption correction given as Bruker SADABS'                           
 
_exptl_special_details 
; 
 ? 
; 
 
_diffrn_ambient_temperature       298(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   'CCD area detector' 
_diffrn_measurement_method        'phi and omega scans' 
_diffrn_detector_area_resol_mean  ? 
_diffrn_standards_number          ? 
_diffrn_standards_interval_count  ? 
_diffrn_standards_interval_time   ? 
_diffrn_standards_decay_%         ? 
_diffrn_reflns_number             7221 
_diffrn_reflns_av_R_equivalents   0.0318 
_diffrn_reflns_av_sigmaI/netI     0.0992 
_diffrn_reflns_limit_h_min        -10 
_diffrn_reflns_limit_h_max        7 
_diffrn_reflns_limit_k_min        -11 
_diffrn_reflns_limit_k_max        11 
_diffrn_reflns_limit_l_min        -19 
_diffrn_reflns_limit_l_max        18 
_diffrn_reflns_theta_min          2.43 
_diffrn_reflns_theta_max          28.41 
_reflns_number_total              4931 
_reflns_number_gt                 2823 
_reflns_threshold_expression      >2sigma(I) 
 
_computing_data_collection      'Bruker SMART'
_computing_cell_refinement      'Bruker SMART'
_computing_data_reduction       'Bruker SHELXTL'
_computing_structure_solution   'Bruker SHELXTL'
_computing_structure_refinement 'Bruker SHELXTL'
_computing_molecular_graphics   'Bruker SHELXTL'
_computing_publication_material 'Bruker SHELXTL'

 
_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^)+(0.0141P)^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     'riding model' 
_refine_ls_extinction_method      none 
_refine_ls_extinction_coef        ? 
_refine_ls_abs_structure_details 
 'Flack H D (1983), Acta Cryst. A39, 876-881' 
_refine_ls_abs_structure_Flack    -0.18(7) 
_refine_ls_number_reflns          4931 
_refine_ls_number_parameters      273 
_refine_ls_number_restraints      1 
_refine_ls_R_factor_all           0.0864 
_refine_ls_R_factor_gt            0.0404 
_refine_ls_wR_factor_ref          0.0697 
_refine_ls_wR_factor_gt           0.0620 
_refine_ls_goodness_of_fit_ref    0.812 
_refine_ls_restrained_S_all       0.796 
_refine_ls_shift/su_max           0.001 
_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 
S1 S 0.71187(12) 0.39672(12) 0.90200(7) 0.0544(3) Uani 1 1 d . . . 
S2 S 0.58366(12) 0.17528(13) 1.02572(7) 0.0610(3) Uani 1 1 d . . . 
S3 S 0.26230(13) 0.15617(12) 0.88082(7) 0.0616(3) Uani 1 1 d . . . 
S4 S 0.41456(12) 0.38416(13) 0.77416(7) 0.0630(3) Uani 1 1 d . . . 
S5 S 0.58458(12) 0.60482(12) 0.64252(7) 0.0529(3) Uani 1 1 d . . . 
S6 S 0.87473(12) 0.61284(12) 0.77511(7) 0.0534(3) Uani 1 1 d . . . 
S7 S 0.75173(12) 0.76544(12) 0.50803(7) 0.0570(3) Uani 1 1 d . . . 
S8 S 1.06341(12) 0.77418(13) 0.65197(7) 0.0574(3) Uani 1 1 d . . . 
C1 C 0.6102(4) 0.4516(5) 0.7983(3) 0.0454(10) Uani 1 1 d . . . 
C2 C 0.5599(4) 0.2772(4) 0.9280(2) 0.0446(10) Uani 1 1 d . . . 
C3 C 0.7825(4) 0.2135(5) 1.0741(3) 0.0774(14) Uani 1 1 d . . . 
H3A H 0.8546 0.1669 1.0398 0.116 Uiso 1 1 calc R . . 
H3B H 0.8007 0.1727 1.1325 0.116 Uiso 1 1 calc R . . 
H3C H 0.7998 0.3217 1.0763 0.116 Uiso 1 1 calc R . . 
C4 C 0.4258(4) 0.2718(4) 0.8702(2) 0.0471(10) Uani 1 1 d . . . 
C5 C 0.1457(5) 0.2738(6) 0.9379(4) 0.110(2) Uani 1 1 d . . . 
H5A H 0.2081 0.3068 0.9918 0.165 Uiso 1 1 calc R . . 
H5B H 0.0547 0.2178 0.9505 0.165 Uiso 1 1 calc R . . 
H5C H 0.1107 0.3611 0.9026 0.165 Uiso 1 1 calc R . . 
C6 C 0.6802(4) 0.5397(4) 0.7451(2) 0.0466(10) Uani 1 1 d . . . 
C7 C 0.8909(4) 0.6811(4) 0.6699(3) 0.0454(10) Uani 1 1 d . . . 
C8 C 0.9812(4) 0.9594(4) 0.6136(3) 0.0493(11) Uani 1 1 d . . . 
H8 H 1.0654 1.0107 0.5876 0.059 Uiso 1 1 calc R . . 
C9 C 0.9438(5) 1.0649(4) 0.6883(3) 0.0515(11) Uani 1 1 d . . . 
H9 H 1.0310 1.0636 0.7378 0.062 Uiso 1 1 calc R . . 
C10 C 0.9173(5) 1.2260(5) 0.6504(3) 0.0721(14) Uani 1 1 d . . . 
H10A H 1.0127 1.2608 0.6289 0.087 Uiso 1 1 calc R . . 
H10B H 0.8950 1.2957 0.6958 0.087 Uiso 1 1 calc R . . 
C11 C 0.7753(6) 1.2242(5) 0.5745(3) 0.0767(14) Uani 1 1 d . . . 
H11A H 0.6947 1.2963 0.5865 0.092 Uiso 1 1 calc R . . 
H11B H 0.8114 1.2540 0.5202 0.092 Uiso 1 1 calc R . . 
C12 C 0.7886(5) 1.0165(4) 0.7167(2) 0.0430(10) Uani 1 1 d . . . 
C13 C 0.7735(5) 0.9834(4) 0.8095(3) 0.0465(10) Uani 1 1 d . . . 
C14 C 0.6136(6) 0.9353(5) 0.8236(3) 0.0645(13) Uani 1 1 d . . . 
H14 H 0.5984 0.9069 0.8798 0.077 Uiso 1 1 calc R . . 
C15 C 0.4896(5) 0.9303(5) 0.7596(3) 0.0671(14) Uani 1 1 d . . . 
H15 H 0.3918 0.8964 0.7723 0.081 Uiso 1 1 calc R . . 
C16 C 0.5023(5) 0.9766(5) 0.6698(3) 0.0514(11) Uani 1 1 d . . . 
C17 C 0.6648(4) 1.0162(4) 0.6529(2) 0.0446(10) Uani 1 1 d . . . 
C18 C 0.7044(5) 1.0640(4) 0.5653(3) 0.0545(11) Uani 1 1 d . . . 
H18 H 0.6089 1.0621 0.5207 0.065 Uiso 1 1 calc R . . 
C19 C 0.8319(4) 0.9555(4) 0.5402(2) 0.0499(11) Uani 1 1 d . . . 
H19 H 0.8665 0.9993 0.4878 0.060 Uiso 1 1 calc R . . 
C20 C 0.7584(5) 0.6772(4) 0.6092(2) 0.0456(10) Uani 1 1 d . . . 
O1 O 0.8817(4) 0.9949(3) 0.86900(18) 0.0730(9) Uani 1 1 d . . . 
O2 O 0.3887(3) 0.9776(4) 0.6114(2) 0.0783(9) Uani 1 1 d . . . 
 
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 0.0399(6) 0.0707(8) 0.0508(7) 0.0103(6) 0.0004(5) -0.0117(6) 
S2 0.0564(7) 0.0748(8) 0.0522(8) 0.0126(6) 0.0101(5) -0.0050(6) 
S3 0.0507(7) 0.0654(8) 0.0702(8) -0.0063(6) 0.0138(6) -0.0194(6) 
S4 0.0457(7) 0.0852(9) 0.0547(8) 0.0127(7) -0.0041(5) -0.0171(6) 
S5 0.0496(7) 0.0551(7) 0.0504(7) 0.0056(6) -0.0039(5) -0.0098(6) 
S6 0.0477(7) 0.0561(7) 0.0528(7) 0.0073(6) -0.0038(5) -0.0115(6) 
S7 0.0732(8) 0.0570(7) 0.0409(7) -0.0048(6) 0.0091(6) -0.0096(6) 
S8 0.0459(7) 0.0602(7) 0.0682(8) 0.0028(6) 0.0155(5) -0.0042(6) 
C1 0.036(2) 0.050(3) 0.047(3) -0.002(2) -0.0012(19) -0.003(2) 
C2 0.039(2) 0.049(2) 0.047(3) 0.000(2) 0.0083(19) -0.002(2) 
C3 0.064(3) 0.095(4) 0.067(3) 0.021(3) -0.006(2) 0.004(3) 
C4 0.041(2) 0.051(3) 0.049(3) 0.004(2) 0.007(2) -0.008(2) 
C5 0.061(3) 0.097(4) 0.186(6) -0.038(4) 0.061(4) -0.015(3) 
C6 0.044(3) 0.041(2) 0.052(3) 0.000(2) -0.001(2) -0.0067(19) 
C7 0.045(2) 0.038(2) 0.054(3) -0.002(2) 0.009(2) -0.0008(19) 
C8 0.044(3) 0.047(2) 0.062(3) 0.000(2) 0.023(2) -0.008(2) 
C9 0.048(3) 0.059(3) 0.047(3) -0.006(2) 0.006(2) -0.012(2) 
C10 0.076(3) 0.056(3) 0.091(4) -0.011(3) 0.036(3) -0.016(3) 
C11 0.114(4) 0.046(3) 0.075(4) 0.013(3) 0.030(3) 0.005(3) 
C12 0.053(3) 0.038(2) 0.040(2) -0.0035(19) 0.013(2) -0.004(2) 
C13 0.053(3) 0.042(2) 0.045(3) -0.008(2) 0.010(2) -0.004(2) 
C14 0.079(4) 0.069(3) 0.052(3) -0.012(3) 0.031(3) -0.009(3) 
C15 0.063(3) 0.071(3) 0.075(4) -0.012(3) 0.035(3) -0.013(3) 
C16 0.041(3) 0.045(3) 0.066(3) -0.003(2) 0.001(2) 0.007(2) 
C17 0.045(3) 0.045(2) 0.044(3) 0.001(2) 0.008(2) -0.002(2) 
C18 0.060(3) 0.061(3) 0.040(3) 0.005(2) 0.001(2) 0.004(2) 
C19 0.068(3) 0.043(2) 0.041(3) 0.004(2) 0.015(2) -0.007(2) 
C20 0.054(3) 0.036(2) 0.047(3) -0.001(2) 0.009(2) -0.001(2) 
O1 0.087(2) 0.087(2) 0.042(2) -0.0046(18) 0.0042(17) -0.016(2) 
O2 0.050(2) 0.074(2) 0.104(3) -0.002(2) -0.0076(17) 0.0071(18) 
 
_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 C2 1.755(4) . ? 
S1 C1 1.765(4) . ? 
S2 C2 1.737(4) . ? 
S2 C3 1.770(4) . ? 
S3 C4 1.746(4) . ? 
S3 C5 1.756(4) . ? 
S4 C1 1.749(4) . ? 
S4 C4 1.770(4) . ? 
S5 C20 1.753(4) . ? 
S5 C6 1.760(4) . ? 
S6 C7 1.756(4) . ? 
S6 C6 1.767(4) . ? 
S7 C20 1.736(4) . ? 
S7 C19 1.840(4) . ? 
S8 C7 1.735(4) . ? 
S8 C8 1.830(4) . ? 
C1 C6 1.331(4) . ? 
C2 C4 1.336(4) . ? 
C7 C20 1.349(5) . ? 
C8 C9 1.548(5) . ? 
C8 C19 1.566(5) . ? 
C9 C12 1.511(5) . ? 
C9 C10 1.533(5) . ? 
C10 C11 1.547(6) . ? 
C11 C18 1.527(5) . ? 
C12 C17 1.325(5) . ? 
C12 C13 1.486(5) . ? 
C13 O1 1.200(4) . ? 
C13 C14 1.468(5) . ? 
C14 C15 1.330(6) . ? 
C15 C16 1.462(6) . ? 
C16 O2 1.216(4) . ? 
C16 C17 1.484(5) . ? 
C17 C18 1.502(5) . ? 
C18 C19 1.533(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 
C2 S1 C1 95.48(19) . . ? 
C2 S2 C3 104.26(19) . . ? 
C4 S3 C5 102.8(2) . . ? 
C1 S4 C4 94.68(18) . . ? 
C20 S5 C6 95.02(19) . . ? 
C7 S6 C6 94.72(19) . . ? 
C20 S7 C19 101.58(17) . . ? 
C7 S8 C8 100.34(17) . . ? 
C6 C1 S4 124.2(3) . . ? 
C6 C1 S1 121.0(3) . . ? 
S4 C1 S1 114.7(2) . . ? 
C4 C2 S2 122.4(3) . . ? 
C4 C2 S1 116.7(3) . . ? 
S2 C2 S1 120.9(2) . . ? 
C2 C4 S3 124.5(3) . . ? 
C2 C4 S4 118.1(3) . . ? 
S3 C4 S4 117.4(2) . . ? 
C1 C6 S5 123.7(3) . . ? 
C1 C6 S6 122.4(3) . . ? 
S5 C6 S6 113.7(2) . . ? 
C20 C7 S8 122.4(3) . . ? 
C20 C7 S6 117.3(3) . . ? 
S8 C7 S6 119.6(2) . . ? 
C9 C8 C19 108.4(3) . . ? 
C9 C8 S8 113.7(3) . . ? 
C19 C8 S8 116.2(3) . . ? 
C12 C9 C10 106.6(3) . . ? 
C12 C9 C8 109.5(3) . . ? 
C10 C9 C8 107.6(3) . . ? 
C9 C10 C11 109.4(3) . . ? 
C18 C11 C10 109.3(3) . . ? 
C17 C12 C13 122.7(4) . . ? 
C17 C12 C9 114.4(3) . . ? 
C13 C12 C9 122.8(3) . . ? 
O1 C13 C14 121.9(4) . . ? 
O1 C13 C12 123.6(4) . . ? 
C14 C13 C12 114.6(4) . . ? 
C15 C14 C13 123.0(4) . . ? 
C14 C15 C16 122.0(4) . . ? 
O2 C16 C15 122.7(4) . . ? 
O2 C16 C17 121.4(4) . . ? 
C15 C16 C17 115.8(4) . . ? 
C12 C17 C16 121.5(4) . . ? 
C12 C17 C18 114.1(3) . . ? 
C16 C17 C18 124.4(4) . . ? 
C17 C18 C11 108.1(3) . . ? 
C17 C18 C19 108.4(3) . . ? 
C11 C18 C19 108.1(3) . . ? 
C18 C19 C8 109.2(3) . . ? 
C18 C19 S7 112.6(3) . . ? 
C8 C19 S7 116.1(3) . . ? 
C7 C20 S7 121.5(3) . . ? 
C7 C20 S5 117.1(3) . . ? 
S7 C20 S5 120.7(2) . . ? 
 
_diffrn_measured_fraction_theta_max    0.920 
_diffrn_reflns_theta_full              28.41 
_diffrn_measured_fraction_theta_full   0.920 
_refine_diff_density_max    0.232 
_refine_diff_density_min   -0.230 
_refine_diff_density_rms    0.048