# Electronic Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and The Centre National de la Recherche Scientifique 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_import _database_code_depnum_ccdc_archive 'CCDC 913393' #TrackingRef 'web_deposit_cif_file_0_CAMEREL_1354286515.FC01.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C11 H8 O S8' _chemical_formula_sum 'C11 H8 O S8' _chemical_formula_weight 412.65 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 triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.1011(17) _cell_length_b 11.4452(18) _cell_length_c 15.124(2) _cell_angle_alpha 69.997(7) _cell_angle_beta 81.790(7) _cell_angle_gamma 73.284(7) _cell_volume 1571.6(4) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 8436 _cell_measurement_theta_min 2.48 _cell_measurement_theta_max 27.35 _exptl_crystal_description prism _exptl_crystal_colour red _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.744 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 840 _exptl_absorpt_coefficient_mu 1.125 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; [Sheldrick, G.M. (2002). SADABS Bruker AXS Inc., Madison, Wisconsin, USA] ; _exptl_absorpt_correction_T_min 0.845 _exptl_absorpt_correction_T_max 0.884 #----------------------------- Remark ------------------------------------# # SADABS output: # # Estimated minimum and maximum transmission: 0.6749 0.7456 # # The ratio of these values is more reliable than their absolute values! # #-------------------------------------------------------------------------# _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_type 'APEXII, Bruker-AXS' _diffrn_measurement_method 'CCD rotation images, thin slices' _diffrn_detector 'CCD plate' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 21733 _diffrn_reflns_av_R_equivalents 0.0322 _diffrn_reflns_av_sigmaI/netI 0.0357 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.43 _diffrn_reflns_theta_max 27.47 _reflns_number_total 7130 _reflns_number_gt 5858 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SAINT' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SIR97 (Altomare et al., 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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^)+(0.0503P)^2^+1.0889P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 7130 _refine_ls_number_parameters 361 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0457 _refine_ls_R_factor_gt 0.0336 _refine_ls_wR_factor_ref 0.1052 _refine_ls_wR_factor_gt 0.0875 _refine_ls_goodness_of_fit_ref 1.089 _refine_ls_restrained_S_all 1.089 _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 C1 C 0.4316(3) 0.1112(2) 0.19951(18) 0.0236(5) Uani 1 1 d . . . C2 C 0.6295(3) 0.0315(2) 0.31660(17) 0.0233(5) Uani 1 1 d . . . H2 H 0.7142 -0.0113 0.3471 0.028 Uiso 1 1 calc R . . C3 C 0.5293(2) 0.1139(2) 0.35098(16) 0.0186(5) Uani 1 1 d . . . C4 C 0.5376(2) 0.1483(2) 0.43408(16) 0.0187(5) Uani 1 1 d . . . C5 C 0.4390(3) 0.2344(2) 0.46609(17) 0.0214(5) Uani 1 1 d . . . H5 H 0.3556 0.2785 0.4342 0.026 Uiso 1 1 calc R . . C6 C 0.6303(3) 0.1521(2) 0.58409(17) 0.0201(5) Uani 1 1 d . . . C7 C 0.7068(3) 0.1320(2) 0.65637(17) 0.0205(5) Uani 1 1 d . . . C8 C 0.8974(3) 0.0559(3) 0.77715(18) 0.0245(5) Uani 1 1 d . . . C9 C 0.7952(3) 0.1411(3) 0.80680(18) 0.0251(5) Uani 1 1 d . . . C10 C 1.0000(3) -0.1683(3) 0.9137(2) 0.0363(7) Uani 1 1 d . . . H10A H 1.0781 -0.2276 0.9511 0.054 Uiso 1 1 calc R . . H10B H 0.9689 -0.2123 0.8784 0.054 Uiso 1 1 calc R . . H10C H 0.9239 -0.1397 0.9558 0.054 Uiso 1 1 calc R . . C11 C 0.6324(4) 0.2004(4) 0.9565(2) 0.0474(8) Uani 1 1 d . . . H11A H 0.6258 0.2252 1.0132 0.071 Uiso 1 1 calc R . . H11B H 0.6090 0.1178 0.9733 0.071 Uiso 1 1 calc R . . H11C H 0.5678 0.2663 0.9109 0.071 Uiso 1 1 calc R . . C12 C 0.6810(3) 0.3497(2) 0.20691(17) 0.0233(5) Uani 1 1 d . . . C13 C 0.7703(3) 0.3712(2) 0.35502(17) 0.0203(5) Uani 1 1 d . . . C14 C 0.6427(3) 0.4524(2) 0.34192(18) 0.0241(5) Uani 1 1 d . . . H14 H 0.6037 0.5024 0.3826 0.029 Uiso 1 1 calc R . . C15 C 0.8604(3) 0.3476(2) 0.43007(17) 0.0200(5) Uani 1 1 d . . . C16 C 0.9886(3) 0.2677(3) 0.44222(18) 0.0243(5) Uani 1 1 d . . . H16 H 1.0281 0.2190 0.4008 0.029 Uiso 1 1 calc R . . C17 C 0.9452(2) 0.3620(2) 0.57975(17) 0.0196(5) Uani 1 1 d . . . C18 C 0.9583(3) 0.3898(2) 0.65727(17) 0.0208(5) Uani 1 1 d . . . C19 C 0.9252(3) 0.4850(3) 0.79526(18) 0.0237(5) Uani 1 1 d . . . C20 C 1.0512(3) 0.4016(2) 0.80508(17) 0.0211(5) Uani 1 1 d . . . C21 C 0.7080(3) 0.5350(3) 0.9229(2) 0.0341(6) Uani 1 1 d . . . H21A H 0.6622 0.5864 0.9641 0.051 Uiso 1 1 calc R . . H21B H 0.7353 0.4440 0.9606 0.051 Uiso 1 1 calc R . . H21C H 0.6440 0.5466 0.8757 0.051 Uiso 1 1 calc R . . C22 C 1.2751(3) 0.2232(3) 0.9018(2) 0.0389(7) Uani 1 1 d . . . H22A H 1.3417 0.2003 0.9501 0.058 Uiso 1 1 calc R . . H22B H 1.3250 0.2257 0.8409 0.058 Uiso 1 1 calc R . . H22C H 1.2216 0.1589 0.9191 0.058 Uiso 1 1 calc R . . O1 O 0.3630(2) 0.1283(2) 0.13499(13) 0.0340(5) Uani 1 1 d . . . O2 O 0.6670(2) 0.31996(19) 0.14041(13) 0.0313(4) Uani 1 1 d . . . S1 S 0.60002(7) 0.00580(7) 0.21604(5) 0.02712(15) Uani 1 1 d . . . S2 S 0.68920(6) 0.07438(6) 0.49777(4) 0.02074(14) Uani 1 1 d . . . S3 S 0.87316(7) 0.02724(6) 0.67400(5) 0.02520(15) Uani 1 1 d . . . S4 S 1.05373(7) -0.03035(7) 0.83225(5) 0.03088(17) Uani 1 1 d . . . S5 S 0.80618(8) 0.18518(8) 0.90517(5) 0.03818(19) Uani 1 1 d . . . S6 S 0.64853(7) 0.21603(6) 0.73906(5) 0.02699(15) Uani 1 1 d . . . S7 S 0.46691(7) 0.26345(6) 0.56610(4) 0.02386(15) Uani 1 1 d . . . S8 S 0.37774(6) 0.18686(6) 0.28868(4) 0.02251(14) Uani 1 1 d . . . S9 S 0.83083(7) 0.28476(6) 0.27471(4) 0.02401(15) Uani 1 1 d . . . S10 S 1.07931(7) 0.25565(6) 0.53500(5) 0.02405(15) Uani 1 1 d . . . S11 S 1.10922(7) 0.31934(6) 0.72164(4) 0.02425(15) Uani 1 1 d . . . S12 S 1.15971(7) 0.37916(7) 0.89335(5) 0.02848(16) Uani 1 1 d . . . S13 S 0.86062(7) 0.58706(7) 0.86388(5) 0.02956(16) Uani 1 1 d . . . S14 S 0.82981(7) 0.50001(6) 0.70095(5) 0.02447(15) Uani 1 1 d . . . S15 S 0.79657(6) 0.43094(6) 0.51295(4) 0.02287(14) Uani 1 1 d . . . S16 S 0.55199(7) 0.46355(6) 0.24973(5) 0.02624(15) 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 C1 0.0267(13) 0.0275(13) 0.0197(12) -0.0089(10) -0.0014(10) -0.0097(11) C2 0.0222(13) 0.0292(13) 0.0196(12) -0.0086(10) -0.0045(10) -0.0054(10) C3 0.0202(12) 0.0200(11) 0.0161(11) -0.0040(9) -0.0042(9) -0.0068(9) C4 0.0203(12) 0.0211(12) 0.0150(11) -0.0027(9) -0.0035(9) -0.0080(9) C5 0.0226(12) 0.0241(12) 0.0189(12) -0.0070(10) -0.0054(10) -0.0058(10) C6 0.0210(12) 0.0199(12) 0.0210(12) -0.0087(9) -0.0021(10) -0.0044(9) C7 0.0213(12) 0.0236(12) 0.0188(12) -0.0095(10) -0.0031(9) -0.0049(10) C8 0.0242(13) 0.0319(14) 0.0216(13) -0.0072(10) -0.0059(10) -0.0127(11) C9 0.0307(14) 0.0321(14) 0.0194(12) -0.0106(10) -0.0047(10) -0.0139(11) C10 0.0365(16) 0.0372(16) 0.0347(16) -0.0073(13) -0.0099(13) -0.0098(13) C11 0.051(2) 0.072(2) 0.0282(16) -0.0269(16) 0.0018(15) -0.0181(18) C12 0.0296(14) 0.0247(13) 0.0191(12) -0.0065(10) -0.0038(10) -0.0114(11) C13 0.0222(12) 0.0233(12) 0.0207(12) -0.0105(10) -0.0022(10) -0.0092(10) C14 0.0268(13) 0.0279(13) 0.0242(13) -0.0146(11) -0.0027(11) -0.0084(11) C15 0.0215(12) 0.0219(12) 0.0202(12) -0.0104(10) -0.0016(10) -0.0065(10) C16 0.0256(13) 0.0304(14) 0.0230(13) -0.0162(11) -0.0021(10) -0.0069(11) C17 0.0199(12) 0.0232(12) 0.0179(12) -0.0079(9) -0.0026(9) -0.0063(10) C18 0.0204(12) 0.0250(12) 0.0190(12) -0.0090(10) -0.0022(9) -0.0059(10) C19 0.0261(13) 0.0316(14) 0.0202(12) -0.0136(10) -0.0012(10) -0.0112(11) C20 0.0272(13) 0.0254(12) 0.0166(12) -0.0083(10) -0.0040(10) -0.0122(10) C21 0.0362(16) 0.0385(16) 0.0274(15) -0.0133(12) 0.0041(12) -0.0083(13) C22 0.0274(15) 0.0549(19) 0.0332(16) -0.0225(14) -0.0097(12) 0.0055(13) O1 0.0363(11) 0.0439(12) 0.0259(10) -0.0167(9) -0.0122(9) -0.0047(9) O2 0.0375(11) 0.0393(11) 0.0227(10) -0.0134(8) -0.0067(8) -0.0115(9) S1 0.0268(3) 0.0346(4) 0.0234(3) -0.0166(3) -0.0034(3) -0.0030(3) S2 0.0207(3) 0.0241(3) 0.0185(3) -0.0099(2) -0.0046(2) -0.0019(2) S3 0.0216(3) 0.0329(3) 0.0233(3) -0.0134(3) -0.0042(2) -0.0036(3) S4 0.0221(3) 0.0437(4) 0.0288(4) -0.0084(3) -0.0074(3) -0.0122(3) S5 0.0434(4) 0.0534(5) 0.0302(4) -0.0234(3) -0.0076(3) -0.0162(4) S6 0.0282(3) 0.0310(3) 0.0259(3) -0.0168(3) -0.0069(3) -0.0019(3) S7 0.0253(3) 0.0247(3) 0.0222(3) -0.0121(2) -0.0058(2) 0.0003(2) S8 0.0227(3) 0.0260(3) 0.0197(3) -0.0095(2) -0.0066(2) -0.0023(2) S9 0.0261(3) 0.0286(3) 0.0214(3) -0.0136(3) -0.0043(2) -0.0049(3) S10 0.0209(3) 0.0303(3) 0.0237(3) -0.0143(3) -0.0042(2) -0.0023(3) S11 0.0239(3) 0.0292(3) 0.0216(3) -0.0128(3) -0.0062(2) -0.0017(3) S12 0.0328(4) 0.0346(4) 0.0241(3) -0.0126(3) -0.0092(3) -0.0101(3) S13 0.0296(4) 0.0371(4) 0.0312(4) -0.0228(3) -0.0018(3) -0.0076(3) S14 0.0235(3) 0.0302(3) 0.0228(3) -0.0144(3) -0.0050(2) -0.0024(3) S15 0.0221(3) 0.0281(3) 0.0216(3) -0.0137(3) -0.0050(2) -0.0023(2) S16 0.0252(3) 0.0301(3) 0.0265(3) -0.0115(3) -0.0071(3) -0.0059(3) _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 O1 1.207(3) . ? C1 S1 1.773(3) . ? C1 S8 1.784(3) . ? C2 C3 1.349(4) . ? C2 S1 1.725(3) . ? C2 H2 0.9500 . ? C3 C4 1.459(3) . ? C3 S8 1.751(2) . ? C4 C5 1.350(3) . ? C4 S2 1.762(2) . ? C5 S7 1.731(3) . ? C5 H5 0.9500 . ? C6 C7 1.346(4) . ? C6 S7 1.762(2) . ? C6 S2 1.766(2) . ? C7 S3 1.756(3) . ? C7 S6 1.767(2) . ? C8 C9 1.343(4) . ? C8 S4 1.755(3) . ? C8 S3 1.763(3) . ? C9 S5 1.753(3) . ? C9 S6 1.755(3) . ? C10 S4 1.810(3) . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 S5 1.800(3) . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C12 O2 1.204(3) . ? C12 S9 1.780(3) . ? C12 S16 1.782(3) . ? C13 C14 1.350(4) . ? C13 C15 1.461(3) . ? C13 S9 1.758(2) . ? C14 S16 1.725(3) . ? C14 H14 0.9500 . ? C15 C16 1.348(4) . ? C15 S15 1.769(2) . ? C16 S10 1.729(3) . ? C16 H16 0.9500 . ? C17 C18 1.347(3) . ? C17 S15 1.762(2) . ? C17 S10 1.769(2) . ? C18 S14 1.760(3) . ? C18 S11 1.761(3) . ? C19 C20 1.346(4) . ? C19 S13 1.750(3) . ? C19 S14 1.767(3) . ? C20 S12 1.752(2) . ? C20 S11 1.762(3) . ? C21 S13 1.817(3) . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? C22 S12 1.803(3) . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? 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 O1 C1 S1 123.0(2) . . ? O1 C1 S8 124.8(2) . . ? S1 C1 S8 112.19(14) . . ? C3 C2 S1 118.45(19) . . ? C3 C2 H2 120.8 . . ? S1 C2 H2 120.8 . . ? C2 C3 C4 125.7(2) . . ? C2 C3 S8 116.53(19) . . ? C4 C3 S8 117.78(18) . . ? C5 C4 C3 125.4(2) . . ? C5 C4 S2 116.55(19) . . ? C3 C4 S2 118.09(18) . . ? C4 C5 S7 119.00(19) . . ? C4 C5 H5 120.5 . . ? S7 C5 H5 120.5 . . ? C7 C6 S7 122.18(19) . . ? C7 C6 S2 122.64(19) . . ? S7 C6 S2 115.13(14) . . ? C6 C7 S3 123.65(19) . . ? C6 C7 S6 121.75(19) . . ? S3 C7 S6 114.55(14) . . ? C9 C8 S4 125.8(2) . . ? C9 C8 S3 117.5(2) . . ? S4 C8 S3 116.68(15) . . ? C8 C9 S5 123.1(2) . . ? C8 C9 S6 117.29(19) . . ? S5 C9 S6 119.50(16) . . ? S4 C10 H10A 109.5 . . ? S4 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? S4 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? S5 C11 H11A 109.5 . . ? S5 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? S5 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? O2 C12 S9 124.5(2) . . ? O2 C12 S16 123.5(2) . . ? S9 C12 S16 112.02(14) . . ? C14 C13 C15 126.1(2) . . ? C14 C13 S9 116.28(19) . . ? C15 C13 S9 117.66(18) . . ? C13 C14 S16 118.6(2) . . ? C13 C14 H14 120.7 . . ? S16 C14 H14 120.7 . . ? C16 C15 C13 125.9(2) . . ? C16 C15 S15 116.66(19) . . ? C13 C15 S15 117.43(18) . . ? C15 C16 S10 118.5(2) . . ? C15 C16 H16 120.7 . . ? S10 C16 H16 120.7 . . ? C18 C17 S15 123.28(19) . . ? C18 C17 S10 122.25(19) . . ? S15 C17 S10 114.45(13) . . ? C17 C18 S14 123.44(19) . . ? C17 C18 S11 121.82(19) . . ? S14 C18 S11 114.73(14) . . ? C20 C19 S13 123.2(2) . . ? C20 C19 S14 117.00(19) . . ? S13 C19 S14 119.58(15) . . ? C19 C20 S12 122.3(2) . . ? C19 C20 S11 117.59(19) . . ? S12 C20 S11 120.04(15) . . ? S13 C21 H21A 109.5 . . ? S13 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? S13 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? S12 C22 H22A 109.5 . . ? S12 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? S12 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C2 S1 C1 96.56(12) . . ? C4 S2 C6 94.60(11) . . ? C7 S3 C8 95.20(12) . . ? C8 S4 C10 99.29(13) . . ? C9 S5 C11 102.06(14) . . ? C9 S6 C7 95.34(12) . . ? C5 S7 C6 94.65(12) . . ? C3 S8 C1 96.27(12) . . ? C13 S9 C12 96.56(12) . . ? C16 S10 C17 95.34(12) . . ? C18 S11 C20 95.25(12) . . ? C20 S12 C22 102.33(13) . . ? C19 S13 C21 102.02(13) . . ? C18 S14 C19 95.41(12) . . ? C17 S15 C15 94.98(11) . . ? C14 S16 C12 96.58(12) . . ? 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 S1 C2 C3 C4 -178.98(19) . . . . ? S1 C2 C3 S8 0.0(3) . . . . ? C2 C3 C4 C5 177.4(2) . . . . ? S8 C3 C4 C5 -1.6(3) . . . . ? C2 C3 C4 S2 -1.5(3) . . . . ? S8 C3 C4 S2 179.48(12) . . . . ? C3 C4 C5 S7 -179.88(19) . . . . ? S2 C4 C5 S7 -0.9(3) . . . . ? S7 C6 C7 S3 -177.15(14) . . . . ? S2 C6 C7 S3 0.0(3) . . . . ? S7 C6 C7 S6 0.1(3) . . . . ? S2 C6 C7 S6 177.31(14) . . . . ? S4 C8 C9 S5 2.8(4) . . . . ? S3 C8 C9 S5 -177.32(15) . . . . ? S4 C8 C9 S6 179.69(15) . . . . ? S3 C8 C9 S6 -0.5(3) . . . . ? C15 C13 C14 S16 -178.8(2) . . . . ? S9 C13 C14 S16 0.2(3) . . . . ? C14 C13 C15 C16 -179.1(3) . . . . ? S9 C13 C15 C16 1.9(4) . . . . ? C14 C13 C15 S15 1.0(4) . . . . ? S9 C13 C15 S15 -177.96(13) . . . . ? C13 C15 C16 S10 179.0(2) . . . . ? S15 C15 C16 S10 -1.1(3) . . . . ? S15 C17 C18 S14 -0.9(3) . . . . ? S10 C17 C18 S14 177.33(13) . . . . ? S15 C17 C18 S11 -179.61(13) . . . . ? S10 C17 C18 S11 -1.3(3) . . . . ? S13 C19 C20 S12 4.3(3) . . . . ? S14 C19 C20 S12 178.37(14) . . . . ? S13 C19 C20 S11 -172.65(14) . . . . ? S14 C19 C20 S11 1.4(3) . . . . ? C3 C2 S1 C1 0.1(2) . . . . ? O1 C1 S1 C2 179.9(2) . . . . ? S8 C1 S1 C2 -0.22(16) . . . . ? C5 C4 S2 C6 2.3(2) . . . . ? C3 C4 S2 C6 -178.72(19) . . . . ? C7 C6 S2 C4 179.8(2) . . . . ? S7 C6 S2 C4 -2.83(16) . . . . ? C6 C7 S3 C8 -180.0(2) . . . . ? S6 C7 S3 C8 2.57(16) . . . . ? C9 C8 S3 C7 -1.3(2) . . . . ? S4 C8 S3 C7 178.56(15) . . . . ? C9 C8 S4 C10 87.9(3) . . . . ? S3 C8 S4 C10 -91.94(17) . . . . ? C8 C9 S5 C11 -142.3(3) . . . . ? S6 C9 S5 C11 40.9(2) . . . . ? C8 C9 S6 C7 2.0(2) . . . . ? S5 C9 S6 C7 178.93(16) . . . . ? C6 C7 S6 C9 179.7(2) . . . . ? S3 C7 S6 C9 -2.77(17) . . . . ? C4 C5 S7 C6 -0.9(2) . . . . ? C7 C6 S7 C5 179.8(2) . . . . ? S2 C6 S7 C5 2.45(16) . . . . ? C2 C3 S8 C1 -0.2(2) . . . . ? C4 C3 S8 C1 178.93(19) . . . . ? O1 C1 S8 C3 -179.9(2) . . . . ? S1 C1 S8 C3 0.23(16) . . . . ? C14 C13 S9 C12 -0.4(2) . . . . ? C15 C13 S9 C12 178.7(2) . . . . ? O2 C12 S9 C13 -179.0(2) . . . . ? S16 C12 S9 C13 0.38(16) . . . . ? C15 C16 S10 C17 2.1(2) . . . . ? C18 C17 S10 C16 179.2(2) . . . . ? S15 C17 S10 C16 -2.35(16) . . . . ? C17 C18 S11 C20 178.8(2) . . . . ? S14 C18 S11 C20 0.02(16) . . . . ? C19 C20 S11 C18 -0.9(2) . . . . ? S12 C20 S11 C18 -177.88(16) . . . . ? C19 C20 S12 C22 159.1(2) . . . . ? S11 C20 S12 C22 -24.0(2) . . . . ? C20 C19 S13 C21 -119.0(2) . . . . ? S14 C19 S13 C21 67.07(19) . . . . ? C17 C18 S14 C19 -178.2(2) . . . . ? S11 C18 S14 C19 0.56(16) . . . . ? C20 C19 S14 C18 -1.2(2) . . . . ? S13 C19 S14 C18 173.12(16) . . . . ? C18 C17 S15 C15 -179.7(2) . . . . ? S10 C17 S15 C15 1.89(16) . . . . ? C16 C15 S15 C17 -0.5(2) . . . . ? C13 C15 S15 C17 179.4(2) . . . . ? C13 C14 S16 C12 0.0(2) . . . . ? O2 C12 S16 C14 179.1(2) . . . . ? S9 C12 S16 C14 -0.28(16) . . . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.583 _refine_diff_density_min -0.426 _refine_diff_density_rms 0.109 data_fcortho _database_code_depnum_ccdc_archive 'CCDC 913394' #TrackingRef 'web_deposit_cif_file_1_CAMEREL_1354286515.FC02.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C16 H14 S12' _chemical_formula_sum 'C16 H14 S12' _chemical_formula_weight 591.11 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' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P n 21 a' _symmetry_space_group_name_Hall 'P -2ac -2n' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' '-x+1/2, y+1/2, z+1/2' 'x+1/2, y, -z+1/2' _cell_length_a 15.341(3) _cell_length_b 29.058(6) _cell_length_c 5.1928(10) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2314.9(8) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 12433 _cell_measurement_theta_min 3.5 _cell_measurement_theta_max 27.49 _exptl_crystal_description plate _exptl_crystal_colour red _exptl_crystal_size_max 0.31 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.696 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1208 _exptl_absorpt_coefficient_mu 1.136 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; [Sheldrick, G.M. (2002). SADABS Bruker AXS Inc., Madison, Wisconsin, USA] ; _exptl_absorpt_correction_T_min 0.849 _exptl_absorpt_correction_T_max 0.966 #----------------------------- Remark ------------------------------------# # SADABS output: # # Estimated minimum and maximum transmission: 0.5768 0.7456 # # The ratio of these values is more reliable than their absolute values! # #-------------------------------------------------------------------------# _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_type 'APEXII, Bruker-AXS' _diffrn_measurement_method 'CCD rotation images, thin slices' _diffrn_detector 'CCD plate' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 36533 _diffrn_reflns_av_R_equivalents 0.0829 _diffrn_reflns_av_sigmaI/netI 0.0552 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -37 _diffrn_reflns_limit_k_max 37 _diffrn_reflns_limit_l_min -6 _diffrn_reflns_limit_l_max 6 _diffrn_reflns_theta_min 3.86 _diffrn_reflns_theta_max 27.50 _reflns_number_total 5302 _reflns_number_gt 4082 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SAINT' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SIR97 (Altomare et al., 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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^)+(0.0910P)^2^+5.0475P] 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 constr _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 0.5(2) _refine_ls_number_reflns 5302 _refine_ls_number_parameters 257 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0891 _refine_ls_R_factor_gt 0.0646 _refine_ls_wR_factor_ref 0.1655 _refine_ls_wR_factor_gt 0.1468 _refine_ls_goodness_of_fit_ref 1.058 _refine_ls_restrained_S_all 1.058 _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 C1 C 0.5220(5) 0.3262(3) -0.6866(17) 0.0217(14) Uani 1 1 d . . . H1 H 0.5044 0.2986 -0.6125 0.026 Uiso 1 1 calc R . . C2 C 0.5953(4) 0.3473(2) -0.6050(13) 0.0191(13) Uani 1 1 d . . . C3 C 0.5310(4) 0.3983(2) -0.9706(13) 0.0208(13) Uani 1 1 d . . . C4 C 0.5195(4) 0.4322(3) -1.1472(13) 0.0229(14) Uani 1 1 d . . . C5 C 0.5333(5) 0.5063(2) -1.4221(13) 0.0240(14) Uani 1 1 d . . . C6 C 0.4593(4) 0.4853(2) -1.5095(13) 0.0237(14) Uani 1 1 d . . . C7 C 0.5608(7) 0.5952(4) -1.2709(15) 0.029(2) Uani 1 1 d . . . H7A H 0.5039 0.6089 -1.2776 0.044 Uiso 1 1 calc R . . H7B H 0.6042 0.6190 -1.2736 0.044 Uiso 1 1 calc R . . H7C H 0.5665 0.5776 -1.1154 0.044 Uiso 1 1 calc R . . C8 C 0.3010(8) 0.4731(5) -1.7526(16) 0.044(3) Uani 1 1 d . . . H8A H 0.3167 0.4413 -1.7673 0.066 Uiso 1 1 calc R . . H8B H 0.2634 0.4814 -1.8929 0.066 Uiso 1 1 calc R . . H8C H 0.2712 0.4781 -1.5925 0.066 Uiso 1 1 calc R . . C9 C 0.6547(4) 0.3311(2) -0.4059(14) 0.0219(14) Uani 1 1 d . . . C10 C 0.7268(5) 0.3530(3) -0.3253(17) 0.0248(15) Uani 1 1 d . . . H10 H 0.7437 0.3808 -0.3994 0.030 Uiso 1 1 calc R . . C11 C 0.7189(4) 0.2804(2) -0.0415(13) 0.0224(14) Uani 1 1 d . . . C12 C 0.7309(4) 0.2474(3) 0.1348(13) 0.0239(14) Uani 1 1 d . . . C13 C 0.7912(4) 0.1928(2) 0.4913(13) 0.0219(13) Uani 1 1 d . . . C14 C 0.7197(5) 0.1721(3) 0.4018(13) 0.0263(14) Uani 1 1 d . . . C15 C 0.9501(8) 0.2038(7) 0.732(2) 0.074(5) Uani 1 1 d . . . H15A H 0.9791 0.1987 0.5709 0.111 Uiso 1 1 calc R . . H15B H 0.9877 0.1947 0.8709 0.111 Uiso 1 1 calc R . . H15C H 0.9361 0.2359 0.7490 0.111 Uiso 1 1 calc R . . C16 C 0.6850(14) 0.0822(6) 0.2494(18) 0.078(6) Uani 1 1 d . . . H16A H 0.6531 0.0952 0.1079 0.117 Uiso 1 1 calc R . . H16B H 0.6609 0.0527 0.2919 0.117 Uiso 1 1 calc R . . H16C H 0.7451 0.0787 0.2018 0.117 Uiso 1 1 calc R . . S1 S 0.46102(10) 0.35108(7) -0.9310(4) 0.0244(4) Uani 1 1 d . . . S2 S 0.43194(11) 0.43236(7) -1.3671(4) 0.0251(4) Uani 1 1 d . . . S3 S 0.3978(2) 0.50797(11) -1.7624(3) 0.0267(7) Uani 1 1 d . . . S4 S 0.57583(14) 0.55746(7) -1.5493(4) 0.0328(4) Uani 1 1 d . . . S5 S 0.59227(12) 0.47814(7) -1.1793(5) 0.0280(4) Uani 1 1 d . . . S6 S 0.6203(2) 0.40001(12) -0.7588(3) 0.0239(6) Uani 1 1 d . . . S7 S 0.78815(10) 0.32826(7) -0.0782(3) 0.0241(4) Uani 1 1 d . . . S8 S 0.81800(11) 0.24692(7) 0.3528(3) 0.0254(4) Uani 1 1 d . . . S9 S 0.8538(2) 0.17119(11) 0.7432(3) 0.0306(8) Uani 1 1 d . . . S10 S 0.67690(13) 0.12045(7) 0.5295(4) 0.0339(4) Uani 1 1 d . . . S11 S 0.65873(12) 0.20022(7) 0.1639(5) 0.0294(4) Uani 1 1 d . . . S12 S 0.62957(19) 0.27898(12) -0.2538(3) 0.0220(6) 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 C1 0.022(4) 0.020(4) 0.024(3) 0.003(3) 0.000(3) -0.005(3) C2 0.018(3) 0.022(3) 0.017(3) -0.001(3) 0.001(2) -0.002(2) C3 0.018(3) 0.026(3) 0.019(3) 0.005(3) -0.001(3) 0.000(3) C4 0.024(3) 0.026(3) 0.019(4) -0.003(3) -0.002(3) -0.001(3) C5 0.029(3) 0.022(3) 0.020(3) 0.001(3) -0.002(3) 0.001(3) C6 0.028(3) 0.020(3) 0.024(4) 0.004(3) 0.002(3) 0.002(3) C7 0.035(5) 0.015(4) 0.037(5) 0.001(3) 0.004(3) -0.007(4) C8 0.035(7) 0.056(7) 0.041(6) 0.019(4) -0.010(3) 0.001(6) C9 0.024(3) 0.017(3) 0.025(3) 0.004(3) -0.002(3) 0.003(3) C10 0.025(4) 0.023(4) 0.026(4) 0.009(4) -0.003(4) 0.002(3) C11 0.018(3) 0.029(3) 0.020(3) -0.003(3) 0.000(3) 0.001(3) C12 0.020(3) 0.022(3) 0.030(4) 0.007(3) -0.003(3) -0.002(3) C13 0.026(3) 0.023(3) 0.017(3) 0.005(3) -0.002(3) 0.000(3) C14 0.024(3) 0.032(4) 0.023(3) 0.005(3) 0.003(3) 0.000(3) C15 0.035(7) 0.133(14) 0.055(8) 0.040(6) -0.014(4) -0.049(8) C16 0.148(16) 0.050(9) 0.037(7) -0.011(4) 0.024(6) -0.039(10) S1 0.0207(8) 0.0275(8) 0.0250(9) 0.0037(7) -0.0052(7) -0.0046(7) S2 0.0226(8) 0.0253(8) 0.0275(10) 0.0039(7) -0.0063(7) -0.0020(6) S3 0.0249(15) 0.0292(18) 0.0259(14) 0.0036(7) -0.0065(6) 0.0049(13) S4 0.0418(10) 0.0297(9) 0.0269(9) 0.0059(8) -0.0011(8) -0.0094(8) S5 0.0246(9) 0.0278(10) 0.0315(10) 0.0065(9) -0.0076(9) -0.0066(7) S6 0.0229(14) 0.0242(16) 0.0244(14) 0.0064(6) -0.0044(6) -0.0064(12) S7 0.0202(8) 0.0264(8) 0.0256(9) 0.0053(7) -0.0041(7) -0.0046(6) S8 0.0239(9) 0.0268(8) 0.0255(9) 0.0048(8) -0.0064(7) -0.0059(7) S9 0.0363(18) 0.0264(18) 0.0291(15) 0.0060(7) -0.0096(8) -0.0019(14) S10 0.0455(11) 0.0288(9) 0.0274(9) 0.0054(8) -0.0029(9) -0.0131(8) S11 0.0270(10) 0.0299(11) 0.0314(12) 0.0086(10) -0.0077(9) -0.0086(8) S12 0.0176(13) 0.0245(16) 0.0239(14) 0.0075(6) -0.0039(6) -0.0036(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 C1 C2 1.350(10) . ? C1 S1 1.735(8) . ? C1 H1 0.9300 . ? C2 C9 1.456(7) . ? C2 S6 1.769(8) . ? C3 C4 1.358(10) . ? C3 S1 1.754(7) . ? C3 S6 1.758(7) . ? C4 S5 1.747(7) . ? C4 S2 1.764(7) . ? C5 C6 1.367(9) . ? C5 S4 1.752(7) . ? C5 S5 1.755(7) . ? C6 S3 1.745(7) . ? C6 S2 1.758(7) . ? C7 S4 1.830(9) . ? C7 H7A 0.9600 . ? C7 H7B 0.9600 . ? C7 H7C 0.9600 . ? C8 S3 1.798(13) . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? C9 C10 1.343(10) . ? C9 S12 1.752(7) . ? C10 S7 1.746(8) . ? C10 H10 0.9300 . ? C11 C12 1.338(10) . ? C11 S12 1.760(7) . ? C11 S7 1.761(7) . ? C12 S8 1.751(7) . ? C12 S11 1.768(7) . ? C13 C14 1.334(10) . ? C13 S9 1.740(7) . ? C13 S8 1.778(7) . ? C14 S11 1.752(7) . ? C14 S10 1.767(7) . ? C15 S9 1.756(13) . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 0.9600 . ? C16 S10 1.835(12) . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 0.9600 . ? 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 C1 S1 119.3(6) . . ? C2 C1 H1 120.4 . . ? S1 C1 H1 120.4 . . ? C1 C2 C9 126.7(6) . . ? C1 C2 S6 115.7(5) . . ? C9 C2 S6 117.7(4) . . ? C4 C3 S1 124.6(5) . . ? C4 C3 S6 120.2(5) . . ? S1 C3 S6 115.2(4) . . ? C3 C4 S5 122.4(5) . . ? C3 C4 S2 122.5(5) . . ? S5 C4 S2 115.0(4) . . ? C6 C5 S4 124.2(5) . . ? C6 C5 S5 117.3(5) . . ? S4 C5 S5 118.4(4) . . ? C5 C6 S3 122.0(5) . . ? C5 C6 S2 116.7(5) . . ? S3 C6 S2 121.2(4) . . ? S4 C7 H7A 109.5 . . ? S4 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? S4 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? S3 C8 H8A 109.5 . . ? S3 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? S3 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C10 C9 C2 125.7(6) . . ? C10 C9 S12 116.8(6) . . ? C2 C9 S12 117.5(4) . . ? C9 C10 S7 118.5(6) . . ? C9 C10 H10 120.7 . . ? S7 C10 H10 120.7 . . ? C12 C11 S12 121.3(5) . . ? C12 C11 S7 123.9(5) . . ? S12 C11 S7 114.8(4) . . ? C11 C12 S8 123.6(5) . . ? C11 C12 S11 121.8(5) . . ? S8 C12 S11 114.6(4) . . ? C14 C13 S9 123.6(6) . . ? C14 C13 S8 116.6(5) . . ? S9 C13 S8 119.7(4) . . ? C13 C14 S11 118.3(6) . . ? C13 C14 S10 123.9(6) . . ? S11 C14 S10 117.5(4) . . ? S9 C15 H15A 109.5 . . ? S9 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? S9 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? S10 C16 H16A 109.5 . . ? S10 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? S10 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C1 S1 C3 94.7(3) . . ? C6 S2 C4 95.3(3) . . ? C6 S3 C8 102.3(4) . . ? C5 S4 C7 99.4(4) . . ? C4 S5 C5 95.5(3) . . ? C3 S6 C2 95.1(3) . . ? C10 S7 C11 94.6(3) . . ? C12 S8 C13 95.3(3) . . ? C13 S9 C15 104.2(5) . . ? C14 S10 C16 101.1(5) . . ? C14 S11 C12 95.0(3) . . ? C9 S12 C11 95.2(4) . . ? 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 S1 C1 C2 C9 -179.0(5) . . . . ? S1 C1 C2 S6 0.9(9) . . . . ? S1 C3 C4 S5 -179.4(4) . . . . ? S6 C3 C4 S5 1.2(9) . . . . ? S1 C3 C4 S2 -1.2(9) . . . . ? S6 C3 C4 S2 179.4(4) . . . . ? S4 C5 C6 S3 -0.2(9) . . . . ? S5 C5 C6 S3 -176.4(4) . . . . ? S4 C5 C6 S2 176.2(4) . . . . ? S5 C5 C6 S2 0.0(8) . . . . ? C1 C2 C9 C10 -179.1(10) . . . . ? S6 C2 C9 C10 0.9(8) . . . . ? C1 C2 C9 S12 -0.1(8) . . . . ? S6 C2 C9 S12 179.9(5) . . . . ? C2 C9 C10 S7 178.6(5) . . . . ? S12 C9 C10 S7 -0.4(9) . . . . ? S12 C11 C12 S8 -179.6(4) . . . . ? S7 C11 C12 S8 -0.5(9) . . . . ? S12 C11 C12 S11 0.5(9) . . . . ? S7 C11 C12 S11 179.6(4) . . . . ? S9 C13 C14 S11 175.1(4) . . . . ? S8 C13 C14 S11 -1.1(8) . . . . ? S9 C13 C14 S10 1.3(10) . . . . ? S8 C13 C14 S10 -174.9(4) . . . . ? C2 C1 S1 C3 0.6(7) . . . . ? C4 C3 S1 C1 178.7(6) . . . . ? S6 C3 S1 C1 -1.9(5) . . . . ? C5 C6 S2 C4 2.3(6) . . . . ? S3 C6 S2 C4 178.8(4) . . . . ? C3 C4 S2 C6 177.7(6) . . . . ? S5 C4 S2 C6 -4.0(4) . . . . ? C5 C6 S3 C8 -169.9(7) . . . . ? S2 C6 S3 C8 13.8(6) . . . . ? C6 C5 S4 C7 114.1(7) . . . . ? S5 C5 S4 C7 -69.7(5) . . . . ? C3 C4 S5 C5 -177.7(6) . . . . ? S2 C4 S5 C5 4.0(4) . . . . ? C6 C5 S5 C4 -2.4(6) . . . . ? S4 C5 S5 C4 -178.8(4) . . . . ? C4 C3 S6 C2 -178.3(6) . . . . ? S1 C3 S6 C2 2.3(5) . . . . ? C1 C2 S6 C3 -1.9(6) . . . . ? C9 C2 S6 C3 178.1(4) . . . . ? C9 C10 S7 C11 -0.4(7) . . . . ? C12 C11 S7 C10 -178.1(7) . . . . ? S12 C11 S7 C10 1.0(5) . . . . ? C11 C12 S8 C13 -176.1(6) . . . . ? S11 C12 S8 C13 3.8(5) . . . . ? C14 C13 S8 C12 -1.6(6) . . . . ? S9 C13 S8 C12 -178.1(4) . . . . ? C14 C13 S9 C15 167.2(9) . . . . ? S8 C13 S9 C15 -16.6(8) . . . . ? C13 C14 S10 C16 -118.4(9) . . . . ? S11 C14 S10 C16 67.8(8) . . . . ? C13 C14 S11 C12 3.2(6) . . . . ? S10 C14 S11 C12 177.5(4) . . . . ? C11 C12 S11 C14 175.7(6) . . . . ? S8 C12 S11 C14 -4.2(5) . . . . ? C10 C9 S12 C11 1.0(7) . . . . ? C2 C9 S12 C11 -178.1(4) . . . . ? C12 C11 S12 C9 177.9(6) . . . . ? S7 C11 S12 C9 -1.2(5) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 1.844 _refine_diff_density_min -0.455 _refine_diff_density_rms 0.152 data_import2 _database_code_depnum_ccdc_archive 'CCDC 913395' #TrackingRef 'web_deposit_cif_file_2_CAMEREL_1354286515.FC03.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C12 H10 O S6' _chemical_formula_sum 'C12 H10 O S6' _chemical_formula_weight 362.56 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M C2/c _symmetry_space_group_name_Hall '-C 2yc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 14.1392(2) _cell_length_b 6.92050(10) _cell_length_c 30.6289(5) _cell_angle_alpha 90.00 _cell_angle_beta 94.1250(10) _cell_angle_gamma 90.00 _cell_volume 2989.28(8) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 9994 _cell_measurement_theta_min 3.5 _cell_measurement_theta_max 27.49 _exptl_crystal_description prism _exptl_crystal_colour orange _exptl_crystal_size_max 0.21 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.611 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1488 _exptl_absorpt_coefficient_mu 0.902 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; [Sheldrick, G.M. (2002). SADABS Bruker AXS Inc., Madison, Wisconsin, USA] ; _exptl_absorpt_correction_T_min 0.897 _exptl_absorpt_correction_T_max 0.947 #----------------------------- Remark ------------------------------------# # SADABS output: # # Estimated minimum and maximum transmission: 0.6190 0.7456 # # The ratio of these values is more reliable than their absolute values! # #-------------------------------------------------------------------------# _diffrn_ambient_temperature 293(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 'APEXII, Bruker-AXS' _diffrn_measurement_method 'CCD rotation images, thin slices' _diffrn_detector 'CCD plate' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 21314 _diffrn_reflns_av_R_equivalents 0.0291 _diffrn_reflns_av_sigmaI/netI 0.0181 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -39 _diffrn_reflns_limit_l_max 39 _diffrn_reflns_theta_min 3.50 _diffrn_reflns_theta_max 27.50 _reflns_number_total 3413 _reflns_number_gt 2835 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SAINT' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SIR97 (Altomare et al., 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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^)+(0.0274P)^2^+4.6919P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3413 _refine_ls_number_parameters 172 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0483 _refine_ls_R_factor_gt 0.0369 _refine_ls_wR_factor_ref 0.0893 _refine_ls_wR_factor_gt 0.0843 _refine_ls_goodness_of_fit_ref 1.156 _refine_ls_restrained_S_all 1.156 _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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.36700(18) 0.6761(3) 0.11281(8) 0.0417(5) Uani 1 1 d . . . C2 C 0.39572(18) 0.8332(4) 0.09188(8) 0.0421(5) Uani 1 1 d . . . C3 C 0.47688(19) 1.1521(4) 0.06905(8) 0.0443(6) Uani 1 1 d . . . C4 C 0.5416(2) 1.3232(4) 0.07345(10) 0.0583(7) Uani 1 1 d . . . H4A H 0.5786 1.3168 0.1010 0.087 Uiso 0.50 1 calc PR . . H4B H 0.5047 1.4397 0.0722 0.087 Uiso 0.50 1 calc PR . . H4C H 0.5831 1.3229 0.0500 0.087 Uiso 0.50 1 calc PR . . H4D H 0.5323 1.4028 0.0478 0.087 Uiso 0.50 1 calc PR . . H4E H 0.6063 1.2799 0.0765 0.087 Uiso 0.50 1 calc PR . . H4F H 0.5278 1.3967 0.0988 0.087 Uiso 0.50 1 calc PR . . C5 C 0.41496(19) 1.1107(4) 0.03545(8) 0.0447(6) Uani 1 1 d . . . C6 C 0.3969(2) 1.2279(5) -0.00557(9) 0.0587(7) Uani 1 1 d . . . H6A H 0.3488 1.1660 -0.0244 0.088 Uiso 0.50 1 calc PR . . H6B H 0.4543 1.2376 -0.0204 0.088 Uiso 0.50 1 calc PR . . H6C H 0.3759 1.3549 0.0018 0.088 Uiso 0.50 1 calc PR . . H6D H 0.4372 1.3396 -0.0042 0.088 Uiso 0.50 1 calc PR . . H6E H 0.3317 1.2681 -0.0083 0.088 Uiso 0.50 1 calc PR . . H6F H 0.4101 1.1508 -0.0305 0.088 Uiso 0.50 1 calc PR . . C7 C 0.28076(17) 0.3576(3) 0.13384(8) 0.0395(5) Uani 1 1 d . . . C8 C 0.21262(19) 0.1917(4) 0.12793(9) 0.0480(6) Uani 1 1 d . . . H8A H 0.1795 0.1994 0.0995 0.072 Uiso 0.50 1 calc PR . . H8B H 0.1678 0.1975 0.1500 0.072 Uiso 0.50 1 calc PR . . H8C H 0.2470 0.0721 0.1305 0.072 Uiso 0.50 1 calc PR . . H8D H 0.2167 0.1132 0.1539 0.072 Uiso 0.50 1 calc PR . . H8E H 0.2284 0.1152 0.1033 0.072 Uiso 0.50 1 calc PR . . H8F H 0.1493 0.2406 0.1228 0.072 Uiso 0.50 1 calc PR . . C9 C 0.34016(16) 0.4002(3) 0.16866(7) 0.0366(5) Uani 1 1 d . . . C10 C 0.35234(16) 0.2970(3) 0.21068(7) 0.0361(5) Uani 1 1 d . . . C11 C 0.37007(18) 0.3802(4) 0.24989(8) 0.0438(6) Uani 1 1 d . . . H11 H 0.3732 0.5140 0.2525 0.053 Uiso 1 1 calc R . . C12 C 0.37588(17) 0.0105(4) 0.26702(8) 0.0433(5) Uani 1 1 d . . . S1 S 0.41479(5) 0.60365(9) 0.16504(2) 0.04531(16) Uani 1 1 d . . . S2 S 0.48466(5) 0.98956(10) 0.11329(2) 0.04806(17) Uani 1 1 d . . . S3 S 0.34834(5) 0.89715(11) 0.03887(2) 0.05114(18) Uani 1 1 d . . . S4 S 0.28152(5) 0.51571(10) 0.08916(2) 0.05142(18) Uani 1 1 d . . . S5 S 0.35156(5) 0.04471(9) 0.21030(2) 0.04834(17) Uani 1 1 d . . . S6 S 0.38697(6) 0.23364(11) 0.29547(2) 0.05545(19) Uani 1 1 d . . . O1 O 0.38448(15) -0.1461(3) 0.28448(6) 0.0602(5) 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 C1 0.0481(14) 0.0338(12) 0.0433(12) 0.0051(10) 0.0034(10) 0.0035(10) C2 0.0481(14) 0.0404(13) 0.0382(11) 0.0066(10) 0.0061(10) 0.0040(11) C3 0.0548(15) 0.0364(13) 0.0428(12) 0.0087(10) 0.0121(11) 0.0032(11) C4 0.0695(19) 0.0445(15) 0.0612(17) 0.0080(13) 0.0071(14) -0.0088(14) C5 0.0534(15) 0.0428(13) 0.0390(12) 0.0096(10) 0.0106(11) 0.0042(11) C6 0.0681(18) 0.0623(18) 0.0459(14) 0.0198(13) 0.0049(13) 0.0051(15) C7 0.0446(13) 0.0315(12) 0.0427(12) 0.0010(9) 0.0063(10) 0.0009(10) C8 0.0485(14) 0.0433(14) 0.0513(14) -0.0033(11) -0.0024(11) -0.0058(11) C9 0.0416(12) 0.0273(11) 0.0416(12) 0.0019(9) 0.0067(9) 0.0010(9) C10 0.0355(12) 0.0298(11) 0.0435(12) 0.0035(9) 0.0061(9) 0.0011(9) C11 0.0548(15) 0.0310(12) 0.0452(13) 0.0027(10) 0.0003(11) 0.0035(11) C12 0.0422(13) 0.0396(13) 0.0481(13) 0.0090(11) 0.0031(10) -0.0010(10) S1 0.0567(4) 0.0326(3) 0.0456(3) 0.0078(2) -0.0030(3) -0.0074(3) S2 0.0589(4) 0.0461(4) 0.0387(3) 0.0101(3) 0.0002(3) -0.0058(3) S3 0.0579(4) 0.0527(4) 0.0421(3) 0.0106(3) -0.0015(3) -0.0063(3) S4 0.0620(4) 0.0456(4) 0.0451(3) 0.0085(3) -0.0064(3) -0.0049(3) S5 0.0716(4) 0.0282(3) 0.0457(3) 0.0032(2) 0.0073(3) -0.0028(3) S6 0.0750(5) 0.0476(4) 0.0424(3) 0.0042(3) -0.0051(3) 0.0055(3) O1 0.0764(14) 0.0418(11) 0.0621(12) 0.0175(9) 0.0042(10) -0.0002(9) _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 C2 1.340(3) . ? C1 S4 1.758(3) . ? C1 S1 1.764(2) . ? C2 S2 1.750(3) . ? C2 S3 1.768(2) . ? C3 C5 1.333(4) . ? C3 C4 1.497(4) . ? C3 S2 1.758(2) . ? C4 H4A 0.9600 . ? C4 H4B 0.9600 . ? C4 H4C 0.9600 . ? C4 H4D 0.9600 . ? C4 H4E 0.9600 . ? C4 H4F 0.9600 . ? C5 C6 1.502(3) . ? C5 S3 1.760(3) . ? C6 H6A 0.9600 . ? C6 H6B 0.9600 . ? C6 H6C 0.9600 . ? C6 H6D 0.9600 . ? C6 H6E 0.9600 . ? C6 H6F 0.9600 . ? C7 C9 1.342(3) . ? C7 C8 1.502(3) . ? C7 S4 1.753(2) . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? C8 H8D 0.9600 . ? C8 H8E 0.9600 . ? C8 H8F 0.9600 . ? C9 C10 1.471(3) . ? C9 S1 1.768(2) . ? C10 C11 1.339(3) . ? C10 S5 1.746(2) . ? C11 S6 1.728(2) . ? C11 H11 0.9300 . ? C12 O1 1.210(3) . ? C12 S5 1.763(3) . ? C12 S6 1.775(3) . ? 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 C1 S4 122.55(19) . . ? C2 C1 S1 123.7(2) . . ? S4 C1 S1 113.68(13) . . ? C1 C2 S2 123.83(19) . . ? C1 C2 S3 122.3(2) . . ? S2 C2 S3 113.83(13) . . ? C5 C3 C4 127.1(2) . . ? C5 C3 S2 117.3(2) . . ? C4 C3 S2 115.64(19) . . ? C3 C4 H4A 109.5 . . ? C3 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? C3 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? C3 C4 H4D 109.5 . . ? H4A C4 H4D 141.1 . . ? H4B C4 H4D 56.3 . . ? H4C C4 H4D 56.3 . . ? C3 C4 H4E 109.5 . . ? H4A C4 H4E 56.3 . . ? H4B C4 H4E 141.1 . . ? H4C C4 H4E 56.3 . . ? H4D C4 H4E 109.5 . . ? C3 C4 H4F 109.5 . . ? H4A C4 H4F 56.3 . . ? H4B C4 H4F 56.3 . . ? H4C C4 H4F 141.1 . . ? H4D C4 H4F 109.5 . . ? H4E C4 H4F 109.5 . . ? C3 C5 C6 126.4(2) . . ? C3 C5 S3 117.31(18) . . ? C6 C5 S3 116.3(2) . . ? C5 C6 H6A 109.5 . . ? C5 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C5 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C5 C6 H6D 109.5 . . ? H6A C6 H6D 141.1 . . ? H6B C6 H6D 56.3 . . ? H6C C6 H6D 56.3 . . ? C5 C6 H6E 109.5 . . ? H6A C6 H6E 56.3 . . ? H6B C6 H6E 141.1 . . ? H6C C6 H6E 56.3 . . ? H6D C6 H6E 109.5 . . ? C5 C6 H6F 109.5 . . ? H6A C6 H6F 56.3 . . ? H6B C6 H6F 56.3 . . ? H6C C6 H6F 141.1 . . ? H6D C6 H6F 109.5 . . ? H6E C6 H6F 109.5 . . ? C9 C7 C8 128.6(2) . . ? C9 C7 S4 116.41(18) . . ? C8 C7 S4 115.04(18) . . ? C7 C8 H8A 109.5 . . ? C7 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C7 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C7 C8 H8D 109.5 . . ? H8A C8 H8D 141.1 . . ? H8B C8 H8D 56.3 . . ? H8C C8 H8D 56.3 . . ? C7 C8 H8E 109.5 . . ? H8A C8 H8E 56.3 . . ? H8B C8 H8E 141.1 . . ? H8C C8 H8E 56.3 . . ? H8D C8 H8E 109.5 . . ? C7 C8 H8F 109.5 . . ? H8A C8 H8F 56.3 . . ? H8B C8 H8F 56.3 . . ? H8C C8 H8F 141.1 . . ? H8D C8 H8F 109.5 . . ? H8E C8 H8F 109.5 . . ? C7 C9 C10 128.0(2) . . ? C7 C9 S1 117.87(17) . . ? C10 C9 S1 114.13(17) . . ? C11 C10 C9 125.3(2) . . ? C11 C10 S5 115.91(18) . . ? C9 C10 S5 118.65(17) . . ? C10 C11 S6 118.55(19) . . ? C10 C11 H11 120.7 . . ? S6 C11 H11 120.7 . . ? O1 C12 S5 124.2(2) . . ? O1 C12 S6 124.0(2) . . ? S5 C12 S6 111.78(13) . . ? C1 S1 C9 95.26(11) . . ? C2 S2 C3 95.94(12) . . ? C5 S3 C2 95.50(12) . . ? C7 S4 C1 96.59(11) . . ? C10 S5 C12 97.30(12) . . ? C11 S6 C12 96.43(12) . . ? 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 S4 C1 C2 S2 -176.78(14) . . . . ? S1 C1 C2 S2 -0.1(3) . . . . ? S4 C1 C2 S3 1.4(3) . . . . ? S1 C1 C2 S3 178.16(14) . . . . ? C4 C3 C5 C6 0.1(4) . . . . ? S2 C3 C5 C6 -179.7(2) . . . . ? C4 C3 C5 S3 179.4(2) . . . . ? S2 C3 C5 S3 -0.4(3) . . . . ? C8 C7 C9 C10 -1.5(4) . . . . ? S4 C7 C9 C10 178.16(19) . . . . ? C8 C7 C9 S1 178.2(2) . . . . ? S4 C7 C9 S1 -2.2(3) . . . . ? C7 C9 C10 C11 -143.6(3) . . . . ? S1 C9 C10 C11 36.7(3) . . . . ? C7 C9 C10 S5 40.8(3) . . . . ? S1 C9 C10 S5 -138.89(14) . . . . ? C9 C10 C11 S6 -177.39(18) . . . . ? S5 C10 C11 S6 -1.7(3) . . . . ? C2 C1 S1 C9 178.7(2) . . . . ? S4 C1 S1 C9 -4.28(15) . . . . ? C7 C9 S1 C1 3.9(2) . . . . ? C10 C9 S1 C1 -176.34(17) . . . . ? C1 C2 S2 C3 -178.3(2) . . . . ? S3 C2 S2 C3 3.38(16) . . . . ? C5 C3 S2 C2 -1.8(2) . . . . ? C4 C3 S2 C2 178.3(2) . . . . ? C3 C5 S3 C2 2.4(2) . . . . ? C6 C5 S3 C2 -178.2(2) . . . . ? C1 C2 S3 C5 178.1(2) . . . . ? S2 C2 S3 C5 -3.54(16) . . . . ? C9 C7 S4 C1 -0.8(2) . . . . ? C8 C7 S4 C1 178.89(19) . . . . ? C2 C1 S4 C7 -179.5(2) . . . . ? S1 C1 S4 C7 3.45(16) . . . . ? C11 C10 S5 C12 0.4(2) . . . . ? C9 C10 S5 C12 176.48(18) . . . . ? O1 C12 S5 C10 -178.8(2) . . . . ? S6 C12 S5 C10 0.82(16) . . . . ? C10 C11 S6 C12 1.9(2) . . . . ? O1 C12 S6 C11 178.2(2) . . . . ? S5 C12 S6 C11 -1.49(16) . . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.206 _refine_diff_density_min -0.267 _refine_diff_density_rms 0.050 data_import3 _database_code_depnum_ccdc_archive 'CCDC 913396' #TrackingRef 'web_deposit_cif_file_3_CAMEREL_1354286515.FC04.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C30 H34 O2 S13' _chemical_formula_sum 'C30 H34 O2 S13' _chemical_formula_weight 843.35 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.569(5) _cell_length_b 14.725(5) _cell_length_c 18.158(5) _cell_angle_alpha 95.476(5) _cell_angle_beta 90.546(5) _cell_angle_gamma 91.274(5) _cell_volume 2013.9(16) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 4267 _cell_measurement_theta_min 2.69 _cell_measurement_theta_max 21.82 _exptl_crystal_description sword _exptl_crystal_colour orange _exptl_crystal_size_max 0.64 _exptl_crystal_size_mid 0.07 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.391 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 876 _exptl_absorpt_coefficient_mu 0.730 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; [Sheldrick, G.M. (2002). SADABS Bruker AXS Inc., Madison, Wisconsin, USA] ; _exptl_absorpt_correction_T_min 0.941 _exptl_absorpt_correction_T_max 0.993 #----------------------------- Remark ------------------------------------# # SADABS output: # # Estimated minimum and maximum transmission: 0.6274 0.7456 # # The ratio of these values is more reliable than their absolute values! # #-------------------------------------------------------------------------# _diffrn_ambient_temperature 293(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 'APEXII, Bruker-AXS' _diffrn_measurement_method 'CCD rotation images, thin slices' _diffrn_detector 'CCD plate' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 29876 _diffrn_reflns_av_R_equivalents 0.0786 _diffrn_reflns_av_sigmaI/netI 0.1192 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 1.13 _diffrn_reflns_theta_max 28.25 _reflns_number_total 9193 _reflns_number_gt 3954 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SAINT' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SIR97 (Altomare et al., 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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^)+(0.1269P)^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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 9193 _refine_ls_number_parameters 416 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1813 _refine_ls_R_factor_gt 0.0668 _refine_ls_wR_factor_ref 0.2442 _refine_ls_wR_factor_gt 0.1683 _refine_ls_goodness_of_fit_ref 0.966 _refine_ls_restrained_S_all 0.966 _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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 1.2216(7) 0.3221(3) 0.5823(3) 0.0561(14) Uani 1 1 d . . . C2 C 1.3243(9) 0.3997(4) 0.4671(3) 0.0636(16) Uani 1 1 d . . . C3 C 1.4559(8) 0.3450(4) 0.4811(3) 0.0618(16) Uani 1 1 d . . . C4 C 1.3122(11) 0.4574(5) 0.4029(4) 0.091(2) Uani 1 1 d . . . H4A H 1.4123 0.4466 0.3714 0.136 Uiso 1 1 calc R . . H4B H 1.3112 0.5207 0.4212 0.136 Uiso 1 1 calc R . . H4C H 1.2056 0.4416 0.3751 0.136 Uiso 1 1 calc R . . C5 C 1.6233(9) 0.3276(5) 0.4377(4) 0.085(2) Uani 1 1 d . . . H5A H 1.6182 0.2669 0.4131 0.127 Uiso 1 1 calc R . . H5B H 1.7235 0.3339 0.4708 0.127 Uiso 1 1 calc R . . H5C H 1.6345 0.3709 0.4016 0.127 Uiso 1 1 calc R . . C6 C 1.1258(7) 0.2856(3) 0.6348(3) 0.0551(14) Uani 1 1 d . . . C7 C 1.0161(7) 0.1830(3) 0.7344(3) 0.0480(13) Uani 1 1 d . . . C8 C 0.8791(7) 0.2345(3) 0.7215(3) 0.0467(13) Uani 1 1 d . . . C9 C 1.0284(7) 0.1164(4) 0.7917(3) 0.0608(15) Uani 1 1 d . . . H9A H 0.9377 0.1282 0.8278 0.091 Uiso 1 1 calc R . . H9B H 1.1422 0.1229 0.8157 0.091 Uiso 1 1 calc R . . H9C H 1.0133 0.0553 0.7684 0.091 Uiso 1 1 calc R . . C10 C 0.7087(7) 0.2318(3) 0.7590(3) 0.0515(14) Uani 1 1 d . . . C11 C 0.6036(7) 0.1567(3) 0.7607(3) 0.0495(13) Uani 1 1 d . . . H11 H 0.5020 0.1620 0.7890 0.059 Uiso 1 1 calc R . . C12 C 0.4521(7) -0.0114(3) 0.7343(3) 0.0478(13) Uani 1 1 d . . . C13 C 0.3427(7) -0.0470(3) 0.6786(3) 0.0464(12) Uani 1 1 d . . . C14 C 0.1822(8) -0.0894(4) 0.5520(3) 0.0584(15) Uani 1 1 d . . . C15 C 0.0824(8) -0.1265(4) 0.6009(3) 0.0596(15) Uani 1 1 d . . . C16 C 0.1528(10) -0.0925(4) 0.4691(3) 0.082(2) Uani 1 1 d . . . H16A H 0.2384 -0.1311 0.4441 0.123 Uiso 1 1 calc R . . H16B H 0.1652 -0.0320 0.4539 0.123 Uiso 1 1 calc R . . H16C H 0.0360 -0.1163 0.4566 0.123 Uiso 1 1 calc R . . C17 C -0.0899(9) -0.1794(5) 0.5874(4) 0.092(2) Uani 1 1 d . . . H17A H -0.1166 -0.1863 0.5353 0.138 Uiso 1 1 calc R . . H17B H -0.1829 -0.1470 0.6132 0.138 Uiso 1 1 calc R . . H17C H -0.0798 -0.2385 0.6050 0.138 Uiso 1 1 calc R . . C18 C 0.7589(10) 0.3839(4) 0.8645(4) 0.083(2) Uani 1 1 d . . . C19 C 1.0235(11) 0.3638(5) 0.9360(4) 0.087(2) Uani 1 1 d . . . H19 H 1.0047 0.4286 0.9508 0.104 Uiso 1 1 calc R . . C20 C 1.1893(16) 0.3544(15) 0.9054(7) 0.304(13) Uani 1 1 d . . . H20A H 1.2647 0.4045 0.9248 0.455 Uiso 1 1 calc R . . H20B H 1.1799 0.3541 0.8526 0.455 Uiso 1 1 calc R . . H20C H 1.2385 0.2981 0.9175 0.455 Uiso 1 1 calc R . . C21 C 1.000(2) 0.3141(13) 0.9984(7) 0.322(14) Uani 1 1 d . . . H21A H 1.0569 0.2564 0.9902 0.483 Uiso 1 1 calc R . . H21B H 0.8760 0.3039 1.0061 0.483 Uiso 1 1 calc R . . H21C H 1.0510 0.3482 1.0414 0.483 Uiso 1 1 calc R . . C22 C 0.6108(8) -0.0642(4) 0.8575(3) 0.0569(14) Uani 1 1 d . . . C23 C 0.6942(9) -0.1462(4) 0.8303(3) 0.0698(17) Uani 1 1 d . . . C24 C 0.8556(11) -0.1551(5) 0.8610(4) 0.103(3) Uani 1 1 d . . . H24 H 0.9292 -0.2039 0.8490 0.124 Uiso 1 1 calc R . . C25 C 0.7109(8) -0.0132(4) 0.9112(3) 0.0666(16) Uani 1 1 d . . . C26 C 0.6700(10) 0.0753(4) 0.9537(3) 0.081(2) Uani 1 1 d . . . H26A H 0.5506 0.0911 0.9433 0.121 Uiso 1 1 calc R . . H26B H 0.7495 0.1221 0.9394 0.121 Uiso 1 1 calc R . . H26C H 0.6837 0.0698 1.0056 0.121 Uiso 1 1 calc R . . C27 C 0.4581(11) -0.2890(4) 0.8093(4) 0.088(2) Uani 1 1 d . . . C28 C 0.2381(16) -0.4118(5) 0.7803(5) 0.126(4) Uani 1 1 d . . . H28 H 0.2423 -0.4175 0.8336 0.151 Uiso 1 1 calc R . . C29 C 0.0747(17) -0.3766(9) 0.7601(11) 0.269(11) Uani 1 1 d . . . H29A H 0.0915 -0.3144 0.7495 0.403 Uiso 1 1 calc R . . H29B H -0.0068 -0.3793 0.8000 0.403 Uiso 1 1 calc R . . H29C H 0.0283 -0.4123 0.7169 0.403 Uiso 1 1 calc R . . C30 C 0.2796(15) -0.4996(5) 0.7385(7) 0.166(5) Uani 1 1 d . . . H30A H 0.2193 -0.5485 0.7600 0.249 Uiso 1 1 calc R . . H30B H 0.4048 -0.5086 0.7403 0.249 Uiso 1 1 calc R . . H30C H 0.2418 -0.4989 0.6879 0.249 Uiso 1 1 calc R . . S1 S 1.1484(2) 0.40708(10) 0.52938(10) 0.0688(5) Uani 1 1 d . . . S2 S 1.4373(2) 0.28592(11) 0.56102(10) 0.0678(5) Uani 1 1 d . . . S3 S 1.2093(2) 0.20017(10) 0.68533(9) 0.0636(4) Uani 1 1 d . . . S4 S 0.9112(2) 0.31892(9) 0.65919(9) 0.0636(4) Uani 1 1 d . . . S5 S 0.64462(19) 0.04997(9) 0.71346(8) 0.0536(4) Uani 1 1 d . . . S6 S 0.3747(2) -0.02961(10) 0.58591(8) 0.0599(4) Uani 1 1 d . . . S7 S 0.1572(2) -0.11484(9) 0.69384(8) 0.0581(4) Uani 1 1 d . . . S8 S 0.6134(2) 0.33549(10) 0.79461(11) 0.0785(5) Uani 1 1 d . . . S9 S 0.7119(4) 0.48569(17) 0.9010(2) 0.1715(14) Uani 1 1 d . . . S10 S 0.40323(19) -0.02923(10) 0.82746(7) 0.0561(4) Uani 1 1 d . . . S11 S 0.9071(3) -0.06540(16) 0.92460(12) 0.1055(7) Uani 1 1 d . . . S12 S 0.6064(3) -0.22572(12) 0.76010(9) 0.0836(6) Uani 1 1 d . . . S13 S 0.4243(4) -0.27561(15) 0.89826(11) 0.1320(10) Uani 1 1 d . . . O1 O 0.8906(6) 0.3311(3) 0.8797(2) 0.0809(13) Uani 1 1 d . . . O2 O 0.3781(8) -0.3477(3) 0.7599(2) 0.1033(18) 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 C1 0.051(4) 0.048(3) 0.069(4) 0.004(3) -0.006(3) 0.000(3) C2 0.079(5) 0.049(3) 0.063(4) 0.004(3) -0.008(3) 0.002(3) C3 0.064(4) 0.057(3) 0.062(4) -0.004(3) 0.003(3) -0.009(3) C4 0.114(6) 0.086(5) 0.075(5) 0.019(4) 0.001(4) 0.006(4) C5 0.088(5) 0.089(5) 0.077(5) 0.010(4) 0.014(4) 0.009(4) C6 0.044(3) 0.049(3) 0.072(4) 0.002(3) -0.012(3) -0.002(3) C7 0.036(3) 0.049(3) 0.057(3) -0.002(2) -0.006(3) 0.001(2) C8 0.038(3) 0.043(3) 0.058(3) -0.003(2) -0.009(3) -0.002(2) C9 0.050(4) 0.059(3) 0.073(4) 0.004(3) -0.009(3) 0.006(3) C10 0.046(4) 0.041(3) 0.066(4) -0.003(2) -0.014(3) 0.009(2) C11 0.035(3) 0.056(3) 0.056(3) -0.005(2) -0.007(2) -0.001(2) C12 0.049(3) 0.045(3) 0.048(3) 0.002(2) -0.002(3) -0.006(2) C13 0.053(3) 0.042(3) 0.042(3) -0.002(2) -0.005(3) -0.002(2) C14 0.063(4) 0.054(3) 0.055(4) -0.006(3) -0.012(3) -0.001(3) C15 0.060(4) 0.053(3) 0.062(4) -0.011(3) -0.014(3) -0.008(3) C16 0.104(6) 0.086(4) 0.055(4) -0.001(3) -0.024(4) -0.001(4) C17 0.067(5) 0.110(5) 0.094(5) -0.005(4) -0.022(4) -0.027(4) C18 0.070(5) 0.067(4) 0.105(6) -0.029(4) 0.007(4) -0.009(4) C19 0.090(6) 0.088(5) 0.076(5) -0.017(4) -0.014(4) -0.014(4) C20 0.106(10) 0.64(4) 0.129(11) -0.098(15) 0.015(8) -0.137(16) C21 0.35(2) 0.48(3) 0.143(11) 0.155(15) -0.133(13) -0.30(2) C22 0.063(4) 0.060(3) 0.047(3) 0.002(3) -0.002(3) 0.001(3) C23 0.078(5) 0.073(4) 0.056(4) -0.004(3) -0.009(3) 0.009(3) C24 0.100(6) 0.107(6) 0.100(6) -0.005(5) -0.035(5) 0.034(5) C25 0.073(4) 0.075(4) 0.049(3) -0.005(3) -0.008(3) -0.005(3) C26 0.094(5) 0.088(4) 0.056(4) -0.012(3) -0.011(4) -0.016(4) C27 0.144(7) 0.053(3) 0.064(4) -0.008(3) -0.005(4) 0.008(4) C28 0.220(12) 0.075(5) 0.079(5) -0.006(4) -0.001(6) -0.052(7) C29 0.138(12) 0.164(12) 0.53(3) 0.122(17) 0.124(16) 0.041(10) C30 0.164(10) 0.064(5) 0.266(14) -0.002(7) -0.038(10) -0.006(6) S1 0.0634(11) 0.0592(8) 0.0854(11) 0.0145(8) -0.0009(9) 0.0076(7) S2 0.0498(10) 0.0716(10) 0.0839(12) 0.0170(8) -0.0016(8) 0.0038(7) S3 0.0433(9) 0.0692(9) 0.0805(11) 0.0171(8) -0.0065(8) 0.0098(7) S4 0.0471(9) 0.0524(8) 0.0933(12) 0.0161(8) -0.0044(8) 0.0063(7) S5 0.0489(9) 0.0553(8) 0.0541(8) -0.0056(6) 0.0001(7) -0.0080(6) S6 0.0672(11) 0.0643(9) 0.0465(8) 0.0012(6) -0.0077(7) -0.0133(7) S7 0.0590(10) 0.0592(8) 0.0541(9) 0.0003(6) -0.0062(7) -0.0173(7) S8 0.0561(11) 0.0567(9) 0.1190(15) -0.0143(9) -0.0029(10) 0.0151(7) S9 0.149(3) 0.0983(17) 0.246(4) -0.096(2) -0.028(2) 0.0306(16) S10 0.0530(10) 0.0692(9) 0.0447(8) -0.0008(6) -0.0033(7) -0.0030(7) S11 0.0899(15) 0.1292(17) 0.0950(15) 0.0009(12) -0.0466(12) 0.0122(12) S12 0.1135(16) 0.0723(10) 0.0621(11) -0.0104(8) -0.0024(10) 0.0099(10) S13 0.226(3) 0.0987(15) 0.0668(13) -0.0058(11) 0.0157(16) -0.0425(17) O1 0.071(3) 0.075(3) 0.089(3) -0.027(2) -0.019(3) 0.000(2) O2 0.176(5) 0.066(3) 0.063(3) -0.012(2) 0.000(3) -0.028(3) _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 C6 1.346(8) . ? C1 S1 1.746(6) . ? C1 S2 1.763(6) . ? C2 C3 1.333(8) . ? C2 C4 1.510(8) . ? C2 S1 1.754(7) . ? C3 C5 1.513(9) . ? C3 S2 1.766(6) . ? C4 H4A 0.9600 . ? C4 H4B 0.9600 . ? C4 H4C 0.9600 . ? C5 H5A 0.9600 . ? C5 H5B 0.9600 . ? C5 H5C 0.9600 . ? C6 S3 1.752(5) . ? C6 S4 1.756(6) . ? C7 C8 1.330(7) . ? C7 C9 1.501(7) . ? C7 S3 1.746(6) . ? C8 C10 1.466(8) . ? C8 S4 1.774(5) . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C10 C11 1.351(7) . ? C10 S8 1.771(5) . ? C11 S5 1.752(5) . ? C11 H11 0.9300 . ? C12 C13 1.360(7) . ? C12 S5 1.760(5) . ? C12 S10 1.778(5) . ? C13 S6 1.744(5) . ? C13 S7 1.745(5) . ? C14 C15 1.321(8) . ? C14 C16 1.517(8) . ? C14 S6 1.761(6) . ? C15 C17 1.510(8) . ? C15 S7 1.766(6) . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 0.9600 . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? C18 O1 1.320(8) . ? C18 S9 1.628(7) . ? C18 S8 1.761(7) . ? C19 C20 1.382(13) . ? C19 C21 1.419(12) . ? C19 O1 1.468(8) . ? C19 H19 0.9800 . ? C20 H20A 0.9600 . ? C20 H20B 0.9600 . ? C20 H20C 0.9600 . ? C21 H21A 0.9600 . ? C21 H21B 0.9600 . ? C21 H21C 0.9600 . ? C22 C25 1.381(8) . ? C22 C23 1.423(8) . ? C22 S10 1.762(6) . ? C23 C24 1.352(9) . ? C23 S12 1.762(6) . ? C24 S11 1.704(8) . ? C24 H24 0.9300 . ? C25 C26 1.490(8) . ? C25 S11 1.713(7) . ? C26 H26A 0.9600 . ? C26 H26B 0.9600 . ? C26 H26C 0.9600 . ? C27 O2 1.318(7) . ? C27 S13 1.631(7) . ? C27 S12 1.750(8) . ? C28 C29 1.410(15) . ? C28 O2 1.477(10) . ? C28 C30 1.478(11) . ? C28 H28 0.9800 . ? C29 H29A 0.9600 . ? C29 H29B 0.9600 . ? C29 H29C 0.9600 . ? C30 H30A 0.9600 . ? C30 H30B 0.9600 . ? C30 H30C 0.9600 . ? 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 C6 C1 S1 124.7(4) . . ? C6 C1 S2 121.6(4) . . ? S1 C1 S2 113.7(3) . . ? C3 C2 C4 126.3(6) . . ? C3 C2 S1 117.4(5) . . ? C4 C2 S1 116.3(5) . . ? C2 C3 C5 128.1(6) . . ? C2 C3 S2 116.9(5) . . ? C5 C3 S2 114.9(5) . . ? C2 C4 H4A 109.5 . . ? C2 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? C2 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? C3 C5 H5A 109.5 . . ? C3 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? C3 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? C1 C6 S3 121.7(4) . . ? C1 C6 S4 123.9(4) . . ? S3 C6 S4 114.3(3) . . ? C8 C7 C9 126.8(5) . . ? C8 C7 S3 117.4(4) . . ? C9 C7 S3 115.6(4) . . ? C7 C8 C10 125.2(5) . . ? C7 C8 S4 117.2(4) . . ? C10 C8 S4 117.4(4) . . ? C7 C9 H9A 109.5 . . ? C7 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C7 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C11 C10 C8 124.9(5) . . ? C11 C10 S8 115.2(4) . . ? C8 C10 S8 119.3(4) . . ? C10 C11 S5 124.9(4) . . ? C10 C11 H11 117.6 . . ? S5 C11 H11 117.6 . . ? C13 C12 S5 119.7(4) . . ? C13 C12 S10 120.0(4) . . ? S5 C12 S10 120.4(3) . . ? C12 C13 S6 123.4(4) . . ? C12 C13 S7 122.6(4) . . ? S6 C13 S7 114.0(3) . . ? C15 C14 C16 127.9(6) . . ? C15 C14 S6 116.9(4) . . ? C16 C14 S6 115.1(5) . . ? C14 C15 C17 128.0(6) . . ? C14 C15 S7 117.2(4) . . ? C17 C15 S7 114.8(5) . . ? C14 C16 H16A 109.5 . . ? C14 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C14 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C15 C17 H17A 109.5 . . ? C15 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C15 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? O1 C18 S9 129.7(5) . . ? O1 C18 S8 114.3(4) . . ? S9 C18 S8 116.0(5) . . ? C20 C19 C21 113.2(13) . . ? C20 C19 O1 108.7(7) . . ? C21 C19 O1 108.4(7) . . ? C20 C19 H19 108.8 . . ? C21 C19 H19 108.8 . . ? O1 C19 H19 108.8 . . ? C19 C20 H20A 109.5 . . ? C19 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C19 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C19 C21 H21A 109.5 . . ? C19 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C19 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C25 C22 C23 112.6(5) . . ? C25 C22 S10 122.5(5) . . ? C23 C22 S10 124.9(4) . . ? C24 C23 C22 112.9(6) . . ? C24 C23 S12 122.3(5) . . ? C22 C23 S12 124.6(5) . . ? C23 C24 S11 111.4(6) . . ? C23 C24 H24 124.3 . . ? S11 C24 H24 124.3 . . ? C22 C25 C26 129.2(6) . . ? C22 C25 S11 110.1(5) . . ? C26 C25 S11 120.7(5) . . ? C25 C26 H26A 109.5 . . ? C25 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C25 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? O2 C27 S13 127.6(6) . . ? O2 C27 S12 106.1(5) . . ? S13 C27 S12 126.3(4) . . ? C29 C28 O2 107.4(8) . . ? C29 C28 C30 113.6(11) . . ? O2 C28 C30 104.6(8) . . ? C29 C28 H28 110.4 . . ? O2 C28 H28 110.4 . . ? C30 C28 H28 110.4 . . ? C28 C29 H29A 109.5 . . ? C28 C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? C28 C29 H29C 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? C28 C30 H30A 109.5 . . ? C28 C30 H30B 109.5 . . ? H30A C30 H30B 109.5 . . ? C28 C30 H30C 109.5 . . ? H30A C30 H30C 109.5 . . ? H30B C30 H30C 109.5 . . ? C1 S1 C2 95.8(3) . . ? C1 S2 C3 95.2(3) . . ? C7 S3 C6 95.9(3) . . ? C6 S4 C8 94.8(3) . . ? C11 S5 C12 100.6(3) . . ? C13 S6 C14 96.0(3) . . ? C13 S7 C15 95.7(3) . . ? C18 S8 C10 106.0(3) . . ? C22 S10 C12 100.2(3) . . ? C24 S11 C25 93.0(3) . . ? C27 S12 C23 101.9(3) . . ? C18 O1 C19 120.0(5) . . ? C27 O2 C28 122.1(6) . . ? 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 C4 C2 C3 C5 0.4(10) . . . . ? S1 C2 C3 C5 -178.7(5) . . . . ? C4 C2 C3 S2 179.3(5) . . . . ? S1 C2 C3 S2 0.2(6) . . . . ? S1 C1 C6 S3 179.9(3) . . . . ? S2 C1 C6 S3 0.2(7) . . . . ? S1 C1 C6 S4 -0.8(7) . . . . ? S2 C1 C6 S4 179.5(3) . . . . ? C9 C7 C8 C10 -3.6(8) . . . . ? S3 C7 C8 C10 -177.9(4) . . . . ? C9 C7 C8 S4 171.4(4) . . . . ? S3 C7 C8 S4 -3.0(6) . . . . ? C7 C8 C10 C11 -57.0(8) . . . . ? S4 C8 C10 C11 128.1(5) . . . . ? C7 C8 C10 S8 132.3(5) . . . . ? S4 C8 C10 S8 -42.7(5) . . . . ? C8 C10 C11 S5 -4.3(8) . . . . ? S8 C10 C11 S5 166.8(3) . . . . ? S5 C12 C13 S6 -4.1(6) . . . . ? S10 C12 C13 S6 177.5(3) . . . . ? S5 C12 C13 S7 175.7(3) . . . . ? S10 C12 C13 S7 -2.7(6) . . . . ? C16 C14 C15 C17 -2.0(10) . . . . ? S6 C14 C15 C17 178.7(5) . . . . ? C16 C14 C15 S7 177.4(5) . . . . ? S6 C14 C15 S7 -1.8(7) . . . . ? C25 C22 C23 C24 -2.0(8) . . . . ? S10 C22 C23 C24 177.9(5) . . . . ? C25 C22 C23 S12 -178.3(5) . . . . ? S10 C22 C23 S12 1.6(8) . . . . ? C22 C23 C24 S11 1.2(9) . . . . ? S12 C23 C24 S11 177.6(4) . . . . ? C23 C22 C25 C26 -179.2(6) . . . . ? S10 C22 C25 C26 0.9(9) . . . . ? C23 C22 C25 S11 1.9(7) . . . . ? S10 C22 C25 S11 -178.0(3) . . . . ? C6 C1 S1 C2 -169.8(5) . . . . ? S2 C1 S1 C2 9.8(4) . . . . ? C3 C2 S1 C1 -6.2(5) . . . . ? C4 C2 S1 C1 174.6(5) . . . . ? C6 C1 S2 C3 170.0(5) . . . . ? S1 C1 S2 C3 -9.8(3) . . . . ? C2 C3 S2 C1 5.8(5) . . . . ? C5 C3 S2 C1 -175.1(4) . . . . ? C8 C7 S3 C6 -0.9(4) . . . . ? C9 C7 S3 C6 -175.9(4) . . . . ? C1 C6 S3 C7 -176.1(5) . . . . ? S4 C6 S3 C7 4.4(3) . . . . ? C1 C6 S4 C8 175.0(5) . . . . ? S3 C6 S4 C8 -5.6(3) . . . . ? C7 C8 S4 C6 5.2(4) . . . . ? C10 C8 S4 C6 -179.4(4) . . . . ? C10 C11 S5 C12 -175.9(5) . . . . ? C13 C12 S5 C11 119.2(4) . . . . ? S10 C12 S5 C11 -62.3(4) . . . . ? C12 C13 S6 C14 -177.2(5) . . . . ? S7 C13 S6 C14 3.0(3) . . . . ? C15 C14 S6 C13 -0.7(5) . . . . ? C16 C14 S6 C13 179.9(4) . . . . ? C12 C13 S7 C15 176.5(5) . . . . ? S6 C13 S7 C15 -3.7(3) . . . . ? C14 C15 S7 C13 3.4(5) . . . . ? C17 C15 S7 C13 -177.1(5) . . . . ? O1 C18 S8 C10 -6.3(6) . . . . ? S9 C18 S8 C10 174.0(4) . . . . ? C11 C10 S8 C18 124.3(5) . . . . ? C8 C10 S8 C18 -64.1(5) . . . . ? C25 C22 S10 C12 114.3(5) . . . . ? C23 C22 S10 C12 -65.5(6) . . . . ? C13 C12 S10 C22 131.9(4) . . . . ? S5 C12 S10 C22 -46.5(4) . . . . ? C23 C24 S11 C25 -0.1(7) . . . . ? C22 C25 S11 C24 -1.0(5) . . . . ? C26 C25 S11 C24 179.9(6) . . . . ? O2 C27 S12 C23 176.6(5) . . . . ? S13 C27 S12 C23 -2.2(6) . . . . ? C24 C23 S12 C27 102.2(7) . . . . ? C22 C23 S12 C27 -81.8(6) . . . . ? S9 C18 O1 C19 -1.5(11) . . . . ? S8 C18 O1 C19 178.9(5) . . . . ? C20 C19 O1 C18 -127.1(12) . . . . ? C21 C19 O1 C18 109.5(12) . . . . ? S13 C27 O2 C28 0.7(12) . . . . ? S12 C27 O2 C28 -178.1(7) . . . . ? C29 C28 O2 C27 102.4(11) . . . . ? C30 C28 O2 C27 -136.7(8) . . . . ? _diffrn_measured_fraction_theta_max 0.924 _diffrn_reflns_theta_full 28.25 _diffrn_measured_fraction_theta_full 0.924 _refine_diff_density_max 0.595 _refine_diff_density_min -0.460 _refine_diff_density_rms 0.114