# Copyright The Royal Society of Chemistry, 1999
# CCDC Number: 1145/150

 
data_sh 
 
_audit_creation_method            SHELXL 
_chemical_name_systematic 
; 
 ? 
; 
_chemical_name_common             ? 
_chemical_formula_moiety          ? 
_chemical_formula_structural      ? 
_chemical_formula_analytical      ? 
_chemical_formula_sum             'C15 H9 N S8' 
_chemical_formula_weight          459.71 
_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' 
 'S'  'S'   0.1246   0.1234 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
 'N'  'N'   0.0061   0.0033 
 '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' 
 'x, -y+1/2, z+1/2' 
 '-x+1/2, -y, z+1/2' 
 '-x, -y, -z' 
 'x-1/2, -y-1/2, -z' 
 '-x, y-1/2, -z-1/2' 
 'x-1/2, y, -z-1/2' 
 
_cell_length_a                    11.448(5) 
_cell_length_b                    35.680(10) 
_cell_length_c                    8.632(3) 
_cell_angle_alpha                 90.00 
_cell_angle_beta                  90.00 
_cell_angle_gamma                 90.00 
_cell_volume                      3525.9(22) 
_cell_formula_units_Z             8 
_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     1.732 
_exptl_crystal_density_method     ? 
_exptl_crystal_F_000              1872 
_exptl_absorpt_coefficient_mu     1.011 
_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             3025 
_diffrn_reflns_av_R_equivalents   0.0000 
_diffrn_reflns_av_sigmaI/netI     0.0673 
_diffrn_reflns_limit_h_min        0 
_diffrn_reflns_limit_h_max        14 
_diffrn_reflns_limit_k_min        0 
_diffrn_reflns_limit_k_max        44 
_diffrn_reflns_limit_l_min        0 
_diffrn_reflns_limit_l_max        10 
_diffrn_reflns_theta_min          2.28 
_diffrn_reflns_theta_max          26.00 
_reflns_number_total              3025 
_reflns_number_observed           2157 
_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-93 (Sheldrick, 1993)' 
_computing_molecular_graphics     ? 
_computing_publication_material   ? 
 
_refine_special_details 
; 
 Refinement on F^2^ for ALL reflections except for 29 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^)+(0.1426P)^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     'all H-atom parameters refined '
_refine_ls_extinction_method      none 
_refine_ls_extinction_coef        ? 
_refine_ls_number_reflns          2996 
_refine_ls_number_parameters      219 
_refine_ls_number_restraints      0 
_refine_ls_R_factor_all           0.1036 
_refine_ls_R_factor_obs           0.0646 
_refine_ls_wR_factor_all          0.2756 
_refine_ls_wR_factor_obs          0.1956 
_refine_ls_goodness_of_fit_all    1.004 
_refine_ls_goodness_of_fit_obs    1.101 
_refine_ls_restrained_S_all       1.320 
_refine_ls_restrained_S_obs       1.101 
_refine_ls_shift/esd_max          0.048 
_refine_ls_shift/esd_mean         0.002 
 
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 
S6 S 0.41738(11) 0.16192(3) 0.1977(2) 0.0437(3) Uani 1 d . . 
S7 S 0.64844(11) 0.06607(3) 0.2004(2) 0.0415(3) Uani 1 d . . 
S5 S 0.62126(10) 0.13839(3) 0.37738(15) 0.0384(3) Uani 1 d . . 
S8 S 0.42003(14) 0.09141(4) 0.0031(2) 0.0536(4) Uani 1 d . . 
S4 S 0.48039(11) 0.24935(3) 0.2705(2) 0.0462(3) Uani 1 d . . 
S2 S 0.54808(12) 0.32904(3) 0.2555(2) 0.0489(3) Uani 1 d . . 
S1 S 0.79456(12) 0.29924(4) 0.4624(2) 0.0562(4) Uani 1 d . . 
S3 S 0.68834(11) 0.22526(3) 0.4426(2) 0.0420(3) Uani 1 d . . 
N N 0.4294(5) -0.01735(14) 0.3115(6) 0.0629(15) Uani 1 d . . 
C1 C 0.7428(6) 0.3452(2) 0.4357(8) 0.070(2) Uani 1 d . . 
H1A H 0.6873(6) 0.3508(2) 0.5173(8) 0.088(11) Uiso 1 calc R . 
H1B H 0.8080(6) 0.3624(2) 0.4468(8) 0.088(11) Uiso 1 calc R . 
C2 C 0.6856(6) 0.3524(2) 0.2834(8) 0.076(2) Uani 1 d . . 
H2A H 0.7385(6) 0.3446(2) 0.2017(8) 0.088(11) Uiso 1 calc R . 
H2B H 0.6734(6) 0.3791(2) 0.2725(8) 0.088(11) Uiso 1 calc R . 
C3 C 0.6770(4) 0.27274(13) 0.3969(6) 0.0370(11) Uani 1 d . . 
C4 C 0.5823(4) 0.28375(13) 0.3174(6) 0.0393(12) Uani 1 d . . 
C5 C 0.5643(4) 0.21172(13) 0.3360(6) 0.0374(12) Uani 1 d . . 
C6 C 0.5385(4) 0.17618(12) 0.3091(6) 0.0348(11) Uani 1 d . . 
C7 C 0.5778(4) 0.10878(12) 0.2242(5) 0.0342(11) Uani 1 d . . 
C8 C 0.4852(4) 0.12039(12) 0.1441(6) 0.0394(12) Uani 1 d . . 
C9 C 0.5220(4) 0.03679(13) 0.1780(6) 0.0383(12) Uani 1 d . . 
C10 C 0.4303(5) 0.04818(13) 0.0961(6) 0.0445(13) Uani 1 d . . 
H10 H 0.3671(5) 0.03192(13) 0.0878(6) 1.000 Uiso 1 calc R . 
C11 C 0.5298(4) 0.00096(12) 0.2597(5) 0.0373(12) Uani 1 d . . 
C12 C 0.6379(4) -0.01232(12) 0.2844(5) 0.0333(11) Uani 1 d . . 
H12 H 0.7033(4) 0.00045(12) 0.2483(5) 1.000 Uiso 1 calc R . 
C13 C 0.6487(5) -0.0443(2) 0.3621(7) 0.052(2) Uani 1 d . . 
H13 H 0.7235(5) -0.0534(2) 0.3800(7) 1.000 Uiso 1 calc R . 
C14 C 0.5540(5) -0.06484(15) 0.4186(6) 0.0518(15) Uani 1 d . . 
H14 H 0.5651(5) -0.08707(15) 0.4729(6) 1.000 Uiso 1 calc R . 
C15 C 0.4436(5) -0.05108(14) 0.3909(7) 0.0501(15) Uani 1 d . . 
H15 H 0.3785(5) -0.06427(14) 0.4252(7) 1.000 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 
S6 0.0410(6) 0.0349(6) 0.0552(7) -0.0060(5) -0.0094(6) 0.0046(5) 
S7 0.0342(6) 0.0369(6) 0.0533(7) 0.0000(5) 0.0068(5) 0.0043(5) 
S5 0.0394(6) 0.0303(5) 0.0455(7) 0.0010(5) -0.0051(6) -0.0017(5) 
S8 0.0771(9) 0.0397(7) 0.0440(7) -0.0037(6) -0.0213(7) 0.0058(7) 
S4 0.0378(6) 0.0348(6) 0.0659(8) 0.0063(6) -0.0114(6) -0.0028(5) 
S2 0.0539(7) 0.0330(6) 0.0598(8) 0.0093(6) -0.0100(7) -0.0015(6) 
S1 0.0504(7) 0.0420(7) 0.0760(10) -0.0028(7) -0.0192(7) -0.0070(6) 
S3 0.0415(6) 0.0338(6) 0.0507(7) 0.0039(5) -0.0080(5) -0.0020(5) 
N 0.070(3) 0.059(3) 0.060(3) -0.008(2) 0.005(3) -0.015(2) 
C1 0.075(4) 0.051(3) 0.085(4) -0.017(3) -0.035(3) -0.003(3) 
C2 0.090(4) 0.044(3) 0.094(5) 0.027(3) -0.044(4) -0.025(3) 
C3 0.035(2) 0.035(2) 0.041(2) 0.006(2) -0.004(2) 0.000(2) 
C4 0.041(2) 0.035(2) 0.042(3) 0.001(2) 0.005(2) -0.011(2) 
C5 0.030(2) 0.041(2) 0.041(3) -0.002(2) 0.002(2) 0.003(2) 
C6 0.036(2) 0.025(2) 0.043(2) 0.000(2) -0.001(2) -0.001(2) 
C7 0.042(2) 0.028(2) 0.032(2) 0.000(2) 0.002(2) -0.001(2) 
C8 0.050(3) 0.024(2) 0.045(3) -0.006(2) -0.004(2) 0.001(2) 
C9 0.041(2) 0.036(2) 0.038(2) -0.009(2) -0.001(2) 0.004(2) 
C10 0.056(3) 0.030(2) 0.047(3) -0.008(2) -0.009(3) -0.001(2) 
C11 0.044(3) 0.037(2) 0.031(2) -0.001(2) 0.003(2) 0.001(2) 
C12 0.035(2) 0.031(2) 0.034(2) 0.002(2) 0.002(2) 0.002(2) 
C13 0.056(3) 0.048(3) 0.053(3) 0.001(3) 0.004(3) 0.012(3) 
C14 0.066(3) 0.039(3) 0.050(3) 0.008(2) 0.009(3) 0.009(2) 
C15 0.059(3) 0.041(3) 0.050(3) 0.000(2) 0.008(3) 0.002(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 
S6 C8 1.736(5) . ? 
S6 C6 1.762(5) . ? 
S7 C7 1.737(5) . ? 
S7 C9 1.796(5) . ? 
S5 C6 1.750(5) . ? 
S5 C7 1.764(5) . ? 
S8 C10 1.743(5) . ? 
S8 C8 1.763(5) . ? 
S4 C4 1.741(5) . ? 
S4 C5 1.745(5) . ? 
S2 C4 1.746(5) . ? 
S2 C2 1.797(6) . ? 
S1 C3 1.739(5) . ? 
S1 C1 1.759(6) . ? 
S3 C3 1.744(5) . ? 
S3 C5 1.760(5) . ? 
N C11 1.396(7) . ? 
N C15 1.395(7) . ? 
C1 C2 1.491(9) . ? 
C1 H1A 0.97 . ? 
C1 H1B 0.97 . ? 
C2 H2A 0.97 . ? 
C2 H2B 0.97 . ? 
C3 C4 1.342(7) . ? 
C5 C6 1.323(6) . ? 
C7 C8 1.332(7) . ? 
C9 C10 1.329(7) . ? 
C9 C11 1.463(6) . ? 
C10 H10 0.93 . ? 
C11 C12 1.342(7) . ? 
C12 C13 1.328(7) . ? 
C12 H12 0.93 . ? 
C13 C14 1.398(8) . ? 
C13 H13 0.93 . ? 
C14 C15 1.376(8) . ? 
C14 H14 0.93 . ? 
C15 H15 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 
C8 S6 C6 92.3(2) . . ? 
C7 S7 C9 98.5(2) . . ? 
C6 S5 C7 93.2(2) . . ? 
C10 S8 C8 99.9(2) . . ? 
C4 S4 C5 95.6(2) . . ? 
C4 S2 C2 101.0(3) . . ? 
C3 S1 C1 101.8(3) . . ? 
C3 S3 C5 95.1(2) . . ? 
C11 N C15 117.8(5) . . ? 
C2 C1 S1 115.0(5) . . ? 
C2 C1 H1A 108.5(4) . . ? 
S1 C1 H1A 108.5(2) . . ? 
C2 C1 H1B 108.5(3) . . ? 
S1 C1 H1B 108.5(2) . . ? 
H1A C1 H1B 107.5 . . ? 
C1 C2 S2 115.1(5) . . ? 
C1 C2 H2A 108.5(4) . . ? 
S2 C2 H2A 108.5(2) . . ? 
C1 C2 H2B 108.5(3) . . ? 
S2 C2 H2B 108.5(2) . . ? 
H2A C2 H2B 107.5 . . ? 
C4 C3 S3 117.4(4) . . ? 
C4 C3 S1 129.2(4) . . ? 
S3 C3 S1 113.4(3) . . ? 
C3 C4 S4 117.0(4) . . ? 
C3 C4 S2 127.5(4) . . ? 
S4 C4 S2 115.5(3) . . ? 
C6 C5 S4 123.9(4) . . ? 
C6 C5 S3 122.4(4) . . ? 
S4 C5 S3 113.7(3) . . ? 
C5 C6 S5 123.9(4) . . ? 
C5 C6 S6 123.3(4) . . ? 
S5 C6 S6 112.8(2) . . ? 
C8 C7 S7 125.6(4) . . ? 
C8 C7 S5 115.3(3) . . ? 
S7 C7 S5 118.9(3) . . ? 
C7 C8 S6 118.9(4) . . ? 
C7 C8 S8 120.9(3) . . ? 
S6 C8 S8 119.7(3) . . ? 
C10 C9 C11 124.9(4) . . ? 
C10 C9 S7 121.1(4) . . ? 
C11 C9 S7 114.0(3) . . ? 
C9 C10 S8 124.7(4) . . ? 
C9 C10 H10 117.7(3) . . ? 
S8 C10 H10 117.7(2) . . ? 
C12 C11 N 122.9(4) . . ? 
C12 C11 C9 116.2(4) . . ? 
N C11 C9 120.8(4) . . ? 
C13 C12 C11 117.9(5) . . ? 
C13 C12 H12 121.0(3) . . ? 
C11 C12 H12 121.0(3) . . ? 
C12 C13 C14 123.7(5) . . ? 
C12 C13 H13 118.1(3) . . ? 
C14 C13 H13 118.1(3) . . ? 
C15 C14 C13 117.7(5) . . ? 
C15 C14 H14 121.2(3) . . ? 
C13 C14 H14 121.2(3) . . ? 
C14 C15 N 120.0(5) . . ? 
C14 C15 H15 120.0(3) . . ? 
N C15 H15 120.0(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 
 C3 S1 C1 C2 -45.6(6) . . . . ? 
 S1 C1 C2 S2 68.6(6) . . . . ? 
 C4 S2 C2 C1 -46.9(5) . . . . ? 
 C5 S3 C3 C4 5.9(4) . . . . ? 
 C5 S3 C3 S1 -173.6(3) . . . . ? 
 C1 S1 C3 C4 12.3(6) . . . . ? 
 C1 S1 C3 S3 -168.2(3) . . . . ? 
 S3 C3 C4 S4 0.6(6) . . . . ? 
 S1 C3 C4 S4 -179.9(3) . . . . ? 
 S3 C3 C4 S2 -179.8(3) . . . . ? 
 S1 C3 C4 S2 -0.3(8) . . . . ? 
 C5 S4 C4 C3 -6.9(4) . . . . ? 
 C5 S4 C4 S2 173.4(3) . . . . ? 
 C2 S2 C4 C3 13.6(6) . . . . ? 
 C2 S2 C4 S4 -166.8(3) . . . . ? 
 C4 S4 C5 C6 -169.4(5) . . . . ? 
 C4 S4 C5 S3 10.7(3) . . . . ? 
 C3 S3 C5 C6 169.7(4) . . . . ? 
 C3 S3 C5 S4 -10.4(3) . . . . ? 
 S4 C5 C6 S5 -178.9(3) . . . . ? 
 S3 C5 C6 S5 1.0(7) . . . . ? 
 S4 C5 C6 S6 2.1(7) . . . . ? 
 S3 C5 C6 S6 -178.0(3) . . . . ? 
 C7 S5 C6 C5 -152.9(5) . . . . ? 
 C7 S5 C6 S6 26.2(3) . . . . ? 
 C8 S6 C6 C5 152.8(5) . . . . ? 
 C8 S6 C6 S5 -26.3(3) . . . . ? 
 C9 S7 C7 C8 -41.5(5) . . . . ? 
 C9 S7 C7 S5 132.5(3) . . . . ? 
 C6 S5 C7 C8 -15.5(4) . . . . ? 
 C6 S5 C7 S7 169.9(3) . . . . ? 
 S7 C7 C8 S6 173.5(3) . . . . ? 
 S5 C7 C8 S6 -0.7(5) . . . . ? 
 S7 C7 C8 S8 1.9(7) . . . . ? 
 S5 C7 C8 S8 -172.3(3) . . . . ? 
 C6 S6 C8 C7 16.4(4) . . . . ? 
 C6 S6 C8 S8 -171.9(3) . . . . ? 
 C10 S8 C8 C7 39.0(5) . . . . ? 
 C10 S8 C8 S6 -132.4(3) . . . . ? 
 C7 S7 C9 C10 40.0(5) . . . . ? 
 C7 S7 C9 C11 -138.7(4) . . . . ? 
 C11 C9 C10 S8 178.3(4) . . . . ? 
 S7 C9 C10 S8 -0.2(7) . . . . ? 
 C8 S8 C10 C9 -40.0(5) . . . . ? 
 C15 N C11 C12 -0.7(8) . . . . ? 
 C15 N C11 C9 -178.9(5) . . . . ? 
 C10 C9 C11 C12 155.2(5) . . . . ? 
 S7 C9 C11 C12 -26.2(6) . . . . ? 
 C10 C9 C11 N -26.5(8) . . . . ? 
 S7 C9 C11 N 152.1(4) . . . . ? 
 N C11 C12 C13 -0.2(7) . . . . ? 
 C9 C11 C12 C13 178.1(5) . . . . ? 
 C11 C12 C13 C14 0.4(8) . . . . ? 
 C12 C13 C14 C15 0.3(9) . . . . ? 
 C13 C14 C15 N -1.1(8) . . . . ? 
 C11 N C15 C14 1.3(8) . . . . ? 
 
_refine_diff_density_max    0.632 
_refine_diff_density_min   -0.381 
_refine_diff_density_rms    0.116