Supplementary Material (ESI) for Chemical Communications This journal is © The Royal Society of Chemistry 2001 data_global _journal_coden_Cambridge 182 _publ_requested_journal 'Chemical Communications' loop_ _publ_author_name 'Coles, Simon J.' 'Hursthouse, Michael B.' 'Khan, Tahir' 'Skabara, Peter J.' _publ_contact_author_name 'Dr Peter J Skabara' _publ_contact_author_address ; Dr Peter J Skabara Department of Chemistry University of Manchester Oxford Road Manchester M13 9PL UNITED KINGDOM ; _publ_contact_author_email 'Peter.Skabara@man.ac.uk' data_s92_6 _database_code_CSD 154927 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C19 H16 O3 S3' _chemical_formula_weight 388.50 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 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.349(2) _cell_length_b 12.081(2) _cell_length_c 15.099(3) _cell_angle_alpha 91.00(3) _cell_angle_beta 103.07(3) _cell_angle_gamma 90.72(3) _cell_volume 1838.3(6) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 19216 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.404 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 808 _exptl_absorpt_coefficient_mu 0.418 _exptl_absorpt_correction_type multi-scans _exptl_absorpt_correction_T_min 0.9210 _exptl_absorpt_correction_T_max 0.9594 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Nonius FR591 rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD Area Detector' _diffrn_measurement_method 'Phi and Omega scans to fill Ewald Sphere' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 27358 _diffrn_reflns_av_R_equivalents 0.0490 _diffrn_reflns_av_sigmaI/netI 0.0542 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 3.04 _diffrn_reflns_theta_max 27.49 _reflns_number_total 8248 _reflns_number_gt 6108 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement 'DENZO, COLLECT' _computing_data_reduction 'DENZO, COLLECT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'CAMERON (Watkin, Pearce 1995)' _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0460P)^2^+0.5015P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0032(9) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 8248 _refine_ls_number_parameters 456 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0651 _refine_ls_R_factor_gt 0.0412 _refine_ls_wR_factor_ref 0.1038 _refine_ls_wR_factor_gt 0.0948 _refine_ls_goodness_of_fit_ref 1.021 _refine_ls_restrained_S_all 1.021 _refine_ls_shift/su_max 0.002 _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 0.8309(2) 0.35761(17) 0.40131(13) 0.0332(5) Uani 1 1 d . . . C2 C 0.88063(19) 0.53889(16) 0.32902(13) 0.0294(4) Uani 1 1 d . . . C3 C 0.99856(19) 0.49802(16) 0.36563(13) 0.0287(4) Uani 1 1 d . . . C4 C 0.89482(19) 0.64585(16) 0.28217(14) 0.0298(4) Uani 1 1 d . . . H4 H 0.8523 0.6370 0.2160 0.036 Uiso 1 1 calc R . . C5 C 1.10862(19) 0.57114(16) 0.34600(14) 0.0297(4) Uani 1 1 d . . . H5 H 1.1650 0.6024 0.4039 0.036 Uiso 1 1 calc R . . C6 C 0.83912(18) 0.74587(15) 0.32030(13) 0.0268(4) Uani 1 1 d . . . C7 C 0.9181(2) 0.83117(17) 0.36601(14) 0.0337(5) Uani 1 1 d . . . H7 H 1.0119 0.8260 0.3768 0.040 Uiso 1 1 calc R . . C8 C 0.8628(2) 0.92429(18) 0.39648(15) 0.0396(5) Uani 1 1 d . . . H8 H 0.9183 0.9828 0.4272 0.048 Uiso 1 1 calc R . . C9 C 0.7272(2) 0.93157(18) 0.38197(14) 0.0366(5) Uani 1 1 d . . . H9 H 0.6893 0.9956 0.4024 0.044 Uiso 1 1 calc R . . C10 C 0.6453(2) 0.84625(17) 0.33782(14) 0.0326(5) Uani 1 1 d . . . H10 H 0.5517 0.8507 0.3292 0.039 Uiso 1 1 calc R . . C11 C 0.70175(18) 0.75472(15) 0.30653(13) 0.0272(4) Uani 1 1 d . . . C12 C 0.4914(2) 0.6636(2) 0.25102(18) 0.0496(6) Uani 1 1 d . . . H12A H 0.4705 0.6673 0.3111 0.074 Uiso 1 1 calc R . . H12B H 0.4543 0.5948 0.2195 0.074 Uiso 1 1 calc R . . H12C H 0.4528 0.7271 0.2155 0.074 Uiso 1 1 calc R . . C13 C 1.19279(18) 0.51107(16) 0.29196(13) 0.0273(4) Uani 1 1 d . . . C14 C 1.17715(19) 0.52215(17) 0.19970(13) 0.0312(4) Uani 1 1 d . . . H14 H 1.1161 0.5742 0.1685 0.037 Uiso 1 1 calc R . . C15 C 1.2493(2) 0.45830(19) 0.15175(15) 0.0404(5) Uani 1 1 d . . . H15 H 1.2369 0.4658 0.0879 0.049 Uiso 1 1 calc R . . C16 C 1.3386(2) 0.38414(19) 0.19701(17) 0.0457(6) Uani 1 1 d . . . H16 H 1.3869 0.3395 0.1638 0.055 Uiso 1 1 calc R . . C17 C 1.3597(2) 0.37319(18) 0.28992(17) 0.0431(6) Uani 1 1 d . . . H17 H 1.4235 0.3230 0.3208 0.052 Uiso 1 1 calc R . . C18 C 1.2865(2) 0.43636(17) 0.33748(14) 0.0345(5) Uani 1 1 d . . . C19 C 1.3831(4) 0.3520(3) 0.4784(2) 0.0866(11) Uani 1 1 d . . . H19A H 1.3564 0.2774 0.4540 0.130 Uiso 1 1 calc R . . H19B H 1.3801 0.3560 0.5428 0.130 Uiso 1 1 calc R . . H19C H 1.4736 0.3684 0.4723 0.130 Uiso 1 1 calc R . . C20 C 0.6997(2) 0.84941(17) 0.08089(13) 0.0310(4) Uani 1 1 d . . . C21 C 0.54653(19) 0.99325(15) 0.12857(12) 0.0260(4) Uani 1 1 d . . . C22 C 0.66783(19) 1.03745(15) 0.15339(12) 0.0264(4) Uani 1 1 d . . . C23 C 0.44660(19) 1.06932(15) 0.15610(13) 0.0275(4) Uani 1 1 d . . . H23 H 0.3756 1.0871 0.1016 0.033 Uiso 1 1 calc R . . C24 C 0.66452(19) 1.14924(16) 0.19845(13) 0.0280(4) Uani 1 1 d . . . H24 H 0.7077 1.1446 0.2646 0.034 Uiso 1 1 calc R . . C25 C 0.38491(18) 1.02218(15) 0.22915(13) 0.0259(4) Uani 1 1 d . . . C26 C 0.41732(19) 1.06133(17) 0.31800(13) 0.0303(4) Uani 1 1 d . . . H26 H 0.4780 1.1219 0.3341 0.036 Uiso 1 1 calc R . . C27 C 0.3626(2) 1.0135(2) 0.38375(15) 0.0394(5) Uani 1 1 d . . . H27 H 0.3851 1.0411 0.4447 0.047 Uiso 1 1 calc R . . C28 C 0.2750(2) 0.9251(2) 0.36012(16) 0.0459(6) Uani 1 1 d . . . H28 H 0.2391 0.8910 0.4057 0.055 Uiso 1 1 calc R . . C29 C 0.2385(2) 0.88508(18) 0.27125(16) 0.0389(5) Uani 1 1 d . . . H29 H 0.1768 0.8251 0.2554 0.047 Uiso 1 1 calc R . . C30 C 0.29373(19) 0.93444(16) 0.20610(14) 0.0301(4) Uani 1 1 d . . . C31 C 0.1714(3) 0.8173(2) 0.08481(19) 0.0602(7) Uani 1 1 d . . . H31A H 0.2002 0.7498 0.1181 0.090 Uiso 1 1 calc R . . H31B H 0.1632 0.8034 0.0196 0.090 Uiso 1 1 calc R . . H31C H 0.0853 0.8393 0.0955 0.090 Uiso 1 1 calc R . . C32 C 0.72661(19) 1.24314(16) 0.15792(13) 0.0279(4) Uani 1 1 d . . . C33 C 0.6525(2) 1.32471(17) 0.10715(13) 0.0317(4) Uani 1 1 d . . . H33 H 0.5584 1.3205 0.0943 0.038 Uiso 1 1 calc R . . C34 C 0.7156(2) 1.41264(18) 0.07498(15) 0.0414(5) Uani 1 1 d . . . H34 H 0.6649 1.4691 0.0411 0.050 Uiso 1 1 calc R . . C35 C 0.8516(2) 1.41726(19) 0.09252(17) 0.0461(6) Uani 1 1 d . . . H35 H 0.8945 1.4779 0.0712 0.055 Uiso 1 1 calc R . . C36 C 0.9275(2) 1.33542(19) 0.14064(16) 0.0431(6) Uani 1 1 d . . . H36 H 1.0215 1.3383 0.1508 0.052 Uiso 1 1 calc R . . C37 C 0.8639(2) 1.24893(17) 0.17382(14) 0.0338(5) Uani 1 1 d . . . C38 C 1.0694(2) 1.1604(2) 0.2373(2) 0.0642(8) Uani 1 1 d . . . H38A H 1.0938 1.1539 0.1785 0.096 Uiso 1 1 calc R . . H38B H 1.1025 1.0965 0.2743 0.096 Uiso 1 1 calc R . . H38C H 1.1085 1.2286 0.2689 0.096 Uiso 1 1 calc R . . O1 O 1.03638(13) 0.65740(11) 0.29338(10) 0.0381(4) Uani 1 1 d . . . O2 O 0.63181(13) 0.66599(11) 0.26119(11) 0.0390(4) Uani 1 1 d . . . O3 O 1.29416(16) 0.43115(14) 0.42897(10) 0.0485(4) Uani 1 1 d . . . O4 O 0.52486(13) 1.16657(11) 0.18826(10) 0.0334(3) Uani 1 1 d . . . O5 O 0.26685(14) 0.90395(12) 0.11560(10) 0.0407(4) Uani 1 1 d . . . O6 O 0.92823(14) 1.16367(13) 0.22326(11) 0.0449(4) Uani 1 1 d . . . S1 S 0.75545(6) 0.25211(5) 0.43791(4) 0.04380(16) Uani 1 1 d . . . S2 S 0.74277(5) 0.46404(4) 0.34087(4) 0.03249(13) Uani 1 1 d . . . S3 S 1.00183(5) 0.37415(4) 0.42094(3) 0.03389(14) Uani 1 1 d . . . S4 S 0.76109(6) 0.74054(5) 0.03854(4) 0.04542(16) Uani 1 1 d . . . S5 S 0.79727(5) 0.96096(4) 0.13219(4) 0.03169(13) Uani 1 1 d . . . S6 S 0.53174(5) 0.86398(4) 0.07689(3) 0.03085(13) 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 0.0503(13) 0.0251(11) 0.0257(11) -0.0024(8) 0.0120(9) 0.0001(9) C2 0.0344(11) 0.0250(10) 0.0308(11) 0.0002(8) 0.0117(8) 0.0017(8) C3 0.0366(11) 0.0247(10) 0.0287(10) 0.0018(8) 0.0148(8) 0.0060(8) C4 0.0263(11) 0.0288(11) 0.0354(11) 0.0039(9) 0.0087(8) 0.0011(8) C5 0.0287(11) 0.0270(11) 0.0354(11) 0.0024(9) 0.0107(8) 0.0046(8) C6 0.0274(10) 0.0243(10) 0.0287(10) 0.0061(8) 0.0056(8) 0.0031(8) C7 0.0250(11) 0.0339(12) 0.0394(12) 0.0022(9) 0.0012(8) 0.0009(8) C8 0.0424(13) 0.0315(12) 0.0401(13) -0.0051(10) -0.0003(9) -0.0001(9) C9 0.0445(13) 0.0316(12) 0.0342(12) 0.0006(9) 0.0094(9) 0.0101(9) C10 0.0262(11) 0.0333(11) 0.0402(12) 0.0109(9) 0.0105(8) 0.0077(8) C11 0.0258(10) 0.0240(10) 0.0307(11) 0.0066(8) 0.0036(8) -0.0004(8) C12 0.0277(13) 0.0421(14) 0.0721(17) 0.0179(12) -0.0038(11) -0.0072(10) C13 0.0260(10) 0.0239(10) 0.0328(11) -0.0038(8) 0.0089(8) -0.0014(8) C14 0.0285(11) 0.0314(11) 0.0338(11) 0.0011(9) 0.0075(8) -0.0076(8) C15 0.0479(14) 0.0437(14) 0.0350(12) -0.0094(10) 0.0223(10) -0.0162(11) C16 0.0529(15) 0.0338(13) 0.0626(16) -0.0071(11) 0.0395(12) -0.0024(11) C17 0.0406(13) 0.0310(12) 0.0651(16) 0.0055(11) 0.0267(11) 0.0102(9) C18 0.0374(12) 0.0323(12) 0.0369(12) 0.0024(9) 0.0140(9) 0.0068(9) C19 0.104(3) 0.102(3) 0.0587(19) 0.0387(18) 0.0225(17) 0.064(2) C20 0.0403(12) 0.0289(11) 0.0246(10) 0.0033(8) 0.0087(8) 0.0043(9) C21 0.0309(11) 0.0240(10) 0.0244(10) 0.0035(8) 0.0085(8) 0.0000(8) C22 0.0321(11) 0.0239(10) 0.0242(10) 0.0029(8) 0.0085(8) 0.0019(8) C23 0.0274(10) 0.0254(10) 0.0308(11) 0.0028(8) 0.0087(8) -0.0003(8) C24 0.0312(11) 0.0240(10) 0.0300(11) -0.0006(8) 0.0097(8) 0.0012(8) C25 0.0251(10) 0.0241(10) 0.0300(10) 0.0065(8) 0.0088(8) 0.0067(7) C26 0.0271(11) 0.0314(11) 0.0341(11) 0.0037(9) 0.0100(8) 0.0070(8) C27 0.0360(12) 0.0533(15) 0.0315(12) 0.0084(10) 0.0120(9) 0.0083(10) C28 0.0379(13) 0.0610(16) 0.0455(14) 0.0257(12) 0.0209(10) 0.0089(11) C29 0.0296(12) 0.0358(12) 0.0537(15) 0.0136(11) 0.0135(10) -0.0018(9) C30 0.0271(11) 0.0283(11) 0.0364(12) 0.0062(9) 0.0096(8) 0.0029(8) C31 0.0495(16) 0.0607(18) 0.0649(18) -0.0133(14) 0.0040(12) -0.0249(13) C32 0.0296(11) 0.0244(10) 0.0301(11) -0.0041(8) 0.0083(8) -0.0024(8) C33 0.0309(11) 0.0313(11) 0.0341(11) 0.0009(9) 0.0098(8) -0.0031(8) C34 0.0455(14) 0.0328(12) 0.0459(13) 0.0093(10) 0.0101(10) -0.0059(10) C35 0.0437(14) 0.0363(13) 0.0594(16) 0.0038(11) 0.0147(11) -0.0172(10) C36 0.0316(12) 0.0372(13) 0.0594(15) -0.0083(11) 0.0093(10) -0.0116(10) C37 0.0310(11) 0.0257(11) 0.0424(12) -0.0088(9) 0.0044(9) -0.0040(8) C38 0.0310(14) 0.0580(17) 0.095(2) -0.0105(16) -0.0039(13) 0.0099(12) O1 0.0289(8) 0.0294(8) 0.0614(10) 0.0134(7) 0.0201(7) 0.0078(6) O2 0.0262(8) 0.0262(8) 0.0598(10) 0.0029(7) -0.0001(6) -0.0023(6) O3 0.0534(10) 0.0552(11) 0.0385(9) 0.0138(8) 0.0117(7) 0.0245(8) O4 0.0336(8) 0.0216(7) 0.0503(9) 0.0014(6) 0.0206(6) -0.0003(6) O5 0.0375(9) 0.0424(9) 0.0416(9) -0.0052(7) 0.0088(6) -0.0105(7) O6 0.0289(8) 0.0362(9) 0.0634(11) -0.0022(8) -0.0030(7) 0.0040(6) S1 0.0634(4) 0.0310(3) 0.0378(3) 0.0033(2) 0.0134(3) -0.0096(3) S2 0.0350(3) 0.0257(3) 0.0378(3) 0.0017(2) 0.0105(2) -0.0022(2) S3 0.0459(3) 0.0271(3) 0.0313(3) 0.0052(2) 0.0135(2) 0.0078(2) S4 0.0609(4) 0.0338(3) 0.0422(3) -0.0065(3) 0.0129(3) 0.0125(3) S5 0.0314(3) 0.0276(3) 0.0369(3) -0.0004(2) 0.0093(2) 0.0051(2) S6 0.0394(3) 0.0264(3) 0.0267(3) -0.0014(2) 0.0078(2) -0.0029(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 C1 S1 1.654(2) . ? C1 S3 1.735(2) . ? C1 S2 1.735(2) . ? C2 C3 1.326(3) . ? C2 C4 1.505(3) . ? C2 S2 1.724(2) . ? C3 C5 1.517(3) . ? C3 S3 1.723(2) . ? C4 O1 1.441(2) . ? C4 C6 1.506(3) . ? C5 O1 1.434(2) . ? C5 C13 1.506(3) . ? C6 C7 1.380(3) . ? C6 C11 1.395(3) . ? C7 C8 1.386(3) . ? C8 C9 1.374(3) . ? C9 C10 1.387(3) . ? C10 C11 1.382(3) . ? C11 O2 1.368(2) . ? C12 O2 1.427(3) . ? C13 C14 1.375(3) . ? C13 C18 1.404(3) . ? C14 C15 1.384(3) . ? C15 C16 1.372(3) . ? C16 C17 1.379(3) . ? C17 C18 1.383(3) . ? C18 O3 1.368(3) . ? C19 O3 1.434(3) . ? C20 S4 1.649(2) . ? C20 S5 1.735(2) . ? C20 S6 1.737(2) . ? C21 C22 1.328(3) . ? C21 C23 1.514(3) . ? C21 S6 1.723(2) . ? C22 C24 1.506(3) . ? C22 S5 1.722(2) . ? C23 O4 1.432(2) . ? C23 C25 1.510(3) . ? C24 O4 1.437(2) . ? C24 C32 1.503(3) . ? C25 C26 1.381(3) . ? C25 C30 1.396(3) . ? C26 C27 1.381(3) . ? C27 C28 1.380(3) . ? C28 C29 1.386(3) . ? C29 C30 1.385(3) . ? C30 O5 1.374(2) . ? C31 O5 1.427(3) . ? C32 C37 1.387(3) . ? C32 C33 1.388(3) . ? C33 C34 1.391(3) . ? C34 C35 1.372(3) . ? C35 C36 1.381(3) . ? C36 C37 1.388(3) . ? C37 O6 1.371(3) . ? C38 O6 1.429(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 S1 C1 S3 124.05(13) . . ? S1 C1 S2 121.82(13) . . ? S3 C1 S2 114.12(12) . . ? C3 C2 C4 110.85(17) . . ? C3 C2 S2 117.38(16) . . ? C4 C2 S2 131.77(15) . . ? C2 C3 C5 110.72(17) . . ? C2 C3 S3 117.40(16) . . ? C5 C3 S3 131.82(15) . . ? O1 C4 C6 110.88(16) . . ? O1 C4 C2 102.74(15) . . ? C6 C4 C2 115.25(16) . . ? O1 C5 C13 110.44(16) . . ? O1 C5 C3 102.48(15) . . ? C13 C5 C3 112.41(16) . . ? C7 C6 C11 118.40(18) . . ? C7 C6 C4 122.76(18) . . ? C11 C6 C4 118.81(17) . . ? C6 C7 C8 121.03(19) . . ? C9 C8 C7 119.7(2) . . ? C8 C9 C10 120.6(2) . . ? C11 C10 C9 119.06(19) . . ? O2 C11 C10 124.64(18) . . ? O2 C11 C6 114.18(17) . . ? C10 C11 C6 121.18(18) . . ? C14 C13 C18 118.86(18) . . ? C14 C13 C5 122.90(18) . . ? C18 C13 C5 118.16(17) . . ? C13 C14 C15 120.8(2) . . ? C16 C15 C14 119.6(2) . . ? C15 C16 C17 121.2(2) . . ? C16 C17 C18 119.1(2) . . ? O3 C18 C17 125.1(2) . . ? O3 C18 C13 114.34(17) . . ? C17 C18 C13 120.5(2) . . ? S4 C20 S5 122.87(13) . . ? S4 C20 S6 123.25(13) . . ? S5 C20 S6 113.88(11) . . ? C22 C21 C23 110.36(17) . . ? C22 C21 S6 117.04(15) . . ? C23 C21 S6 132.56(15) . . ? C21 C22 C24 110.68(17) . . ? C21 C22 S5 117.61(15) . . ? C24 C22 S5 131.69(14) . . ? O4 C23 C25 111.30(16) . . ? O4 C23 C21 102.54(15) . . ? C25 C23 C21 113.18(16) . . ? O4 C24 C32 110.34(16) . . ? O4 C24 C22 102.67(15) . . ? C32 C24 C22 115.68(16) . . ? C26 C25 C30 118.99(18) . . ? C26 C25 C23 122.39(18) . . ? C30 C25 C23 118.61(17) . . ? C25 C26 C27 120.8(2) . . ? C28 C27 C26 119.4(2) . . ? C27 C28 C29 121.3(2) . . ? C30 C29 C28 118.5(2) . . ? O5 C30 C29 125.07(19) . . ? O5 C30 C25 113.97(17) . . ? C29 C30 C25 120.97(19) . . ? C37 C32 C33 119.10(18) . . ? C37 C32 C24 118.12(18) . . ? C33 C32 C24 122.77(18) . . ? C32 C33 C34 120.3(2) . . ? C35 C34 C33 119.6(2) . . ? C34 C35 C36 121.3(2) . . ? C35 C36 C37 118.8(2) . . ? O6 C37 C32 114.81(18) . . ? O6 C37 C36 124.24(19) . . ? C32 C37 C36 120.9(2) . . ? C5 O1 C4 113.13(15) . . ? C11 O2 C12 117.95(17) . . ? C18 O3 C19 116.93(19) . . ? C23 O4 C24 112.64(14) . . ? C30 O5 C31 118.14(18) . . ? C37 O6 C38 117.89(19) . . ? C2 S2 C1 95.53(10) . . ? C3 S3 C1 95.57(10) . . ? C22 S5 C20 95.62(10) . . ? C21 S6 C20 95.83(10) . . ? _diffrn_measured_fraction_theta_max 0.977 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.977 _refine_diff_density_max 0.324 _refine_diff_density_min -0.350 _refine_diff_density_rms 0.054 data_s92_8 _database_code_CSD 154928 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H20 O5 S3' _chemical_formula_weight 448.55 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)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 12.732(3) _cell_length_b 13.131(3) _cell_length_c 13.040(3) _cell_angle_alpha 90.00 _cell_angle_beta 96.88(3) _cell_angle_gamma 90.00 _cell_volume 2164.3(7) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 16442 _cell_measurement_theta_min 2.11 _cell_measurement_theta_max 27.53 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.377 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 936 _exptl_absorpt_coefficient_mu 0.372 _exptl_absorpt_correction_type multi-scans _exptl_absorpt_correction_T_min 0.856 _exptl_absorpt_correction_T_max 0.970 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Nonius FR591 rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD Area Detector' _diffrn_measurement_method 'Phi and Omega scans to fill Ewald Sphere' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16442 _diffrn_reflns_av_R_equivalents 0.0533 _diffrn_reflns_av_sigmaI/netI 0.0606 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.11 _diffrn_reflns_theta_max 27.53 _reflns_number_total 4938 _reflns_number_gt 2899 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement 'DENZO, COLLECT' _computing_data_reduction 'DENZO, COLLECT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'CAMERON (Watkin, Pearce 1995)' _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0784P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4938 _refine_ls_number_parameters 266 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1006 _refine_ls_R_factor_gt 0.0493 _refine_ls_wR_factor_ref 0.1432 _refine_ls_wR_factor_gt 0.1220 _refine_ls_goodness_of_fit_ref 0.991 _refine_ls_restrained_S_all 0.991 _refine_ls_shift/su_max 0.008 _refine_ls_shift/su_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_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 1.04396(6) 0.14506(6) 0.47927(7) 0.0835(3) Uani 1 1 d . . . S2 S 0.86190(5) 0.14022(5) 0.60175(5) 0.0589(2) Uani 1 1 d . . . S3 S 0.82485(5) 0.10889(4) 0.38112(5) 0.0532(2) Uani 1 1 d . . . O1 O 0.66452(16) 0.14926(15) 0.70684(16) 0.0817(6) Uani 1 1 d . . . O2 O 0.61835(14) -0.09741(10) 0.35677(12) 0.0553(4) Uani 1 1 d . . . O3 O 0.64505(15) -0.08764(14) -0.00208(13) 0.0722(5) Uani 1 1 d . . . O4 O 0.38972(12) 0.13335(10) 0.36548(14) 0.0542(4) Uani 1 1 d . . . O5 O 0.40366(13) 0.49413(11) 0.35609(15) 0.0692(5) Uani 1 1 d . . . C1 C 0.91741(19) 0.13293(16) 0.4882(2) 0.0535(6) Uani 1 1 d . . . C2 C 0.73085(18) 0.12437(15) 0.54783(18) 0.0467(5) Uani 1 1 d . . . C3 C 0.71304(17) 0.11149(14) 0.44408(17) 0.0419(5) Uani 1 1 d . . . C4 C 0.6479(2) 0.13023(17) 0.6157(2) 0.0575(6) Uani 1 1 d . . . H4 H 0.5784 0.1187 0.5872 0.069 Uiso 1 1 calc R . . C5 C 0.60530(17) 0.10811(14) 0.37976(17) 0.0426(5) Uani 1 1 d . . . H5 H 0.5601 0.0635 0.4158 0.051 Uiso 1 1 calc R . . C6 C 0.61327(16) 0.06058(15) 0.27404(17) 0.0435(5) Uani 1 1 d . . . C7 C 0.62081(17) -0.04504(15) 0.26612(17) 0.0451(5) Uani 1 1 d . . . C8 C 0.63028(18) -0.09097(16) 0.17271(18) 0.0507(6) Uani 1 1 d . . . H8 H 0.6337 -0.1616 0.1684 0.061 Uiso 1 1 calc R . . C9 C 0.63471(18) -0.03214(18) 0.08518(19) 0.0542(6) Uani 1 1 d . . . C10 C 0.62699(19) 0.07271(19) 0.09067(19) 0.0590(6) Uani 1 1 d . . . H10 H 0.6299 0.1126 0.0321 0.071 Uiso 1 1 calc R . . C11 C 0.6150(2) 0.11724(17) 0.1842(2) 0.0541(6) Uani 1 1 d . . . H11 H 0.6078 0.1876 0.1874 0.065 Uiso 1 1 calc R . . C12 C 0.6322(3) -0.20361(17) 0.3543(2) 0.0900(11) Uani 1 1 d . . . H12A H 0.5820 -0.2324 0.3013 0.135 Uiso 1 1 calc R . . H12B H 0.6212 -0.2321 0.4200 0.135 Uiso 1 1 calc R . . H12C H 0.7026 -0.2188 0.3398 0.135 Uiso 1 1 calc R . . C13 C 0.6506(3) -0.0322(2) -0.0955(2) 0.0881(10) Uani 1 1 d . . . H13A H 0.5914 0.0134 -0.1070 0.132 Uiso 1 1 calc R . . H13B H 0.6489 -0.0790 -0.1523 0.132 Uiso 1 1 calc R . . H13C H 0.7152 0.0062 -0.0900 0.132 Uiso 1 1 calc R . . C14 C 0.55462(16) 0.21377(15) 0.37431(16) 0.0437(5) Uani 1 1 d . . . C15 C 0.44478(16) 0.22291(15) 0.36743(16) 0.0407(5) Uani 1 1 d . . . C16 C 0.39753(17) 0.31796(15) 0.36301(17) 0.0456(5) Uani 1 1 d . . . H16 H 0.3244 0.3235 0.3603 0.055 Uiso 1 1 calc R . . C17 C 0.45930(18) 0.40479(15) 0.36255(18) 0.0488(6) Uani 1 1 d . . . C18 C 0.5671(2) 0.39798(16) 0.3688(2) 0.0599(7) Uani 1 1 d . . . H18 H 0.6086 0.4562 0.3686 0.072 Uiso 1 1 calc R . . C19 C 0.61279(18) 0.30197(16) 0.3754(2) 0.0612(7) Uani 1 1 d . . . H19 H 0.6861 0.2971 0.3807 0.073 Uiso 1 1 calc R . . C20 C 0.2768(2) 0.13910(18) 0.3551(3) 0.0762(9) Uani 1 1 d . . . H20A H 0.2549 0.1710 0.4153 0.114 Uiso 1 1 calc R . . H20B H 0.2476 0.0717 0.3480 0.114 Uiso 1 1 calc R . . H20C H 0.2521 0.1785 0.2950 0.114 Uiso 1 1 calc R . . C21 C 0.4610(2) 0.58590(17) 0.3486(2) 0.0784(9) Uani 1 1 d . . . H21A H 0.5158 0.5906 0.4058 0.118 Uiso 1 1 calc R . . H21B H 0.4140 0.6429 0.3499 0.118 Uiso 1 1 calc R . . H21C H 0.4922 0.5863 0.2851 0.118 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.0375(4) 0.1026(6) 0.1117(7) -0.0114(4) 0.0138(4) -0.0064(3) S2 0.0442(4) 0.0726(4) 0.0583(4) -0.0033(3) 0.0000(3) 0.0008(3) S3 0.0388(4) 0.0653(4) 0.0569(4) -0.0005(3) 0.0117(3) 0.0019(3) O1 0.0689(14) 0.1211(16) 0.0570(14) -0.0154(11) 0.0154(10) -0.0027(11) O2 0.0724(12) 0.0433(8) 0.0519(10) 0.0045(7) 0.0143(9) 0.0058(7) O3 0.0737(14) 0.0943(13) 0.0496(11) -0.0101(9) 0.0110(10) 0.0051(10) O4 0.0325(9) 0.0476(8) 0.0819(12) 0.0020(7) 0.0049(8) -0.0046(7) O5 0.0572(11) 0.0440(9) 0.1060(15) -0.0022(8) 0.0075(10) 0.0100(8) C1 0.0357(13) 0.0554(13) 0.0692(17) 0.0003(11) 0.0055(12) 0.0031(10) C2 0.0398(13) 0.0487(12) 0.0521(15) -0.0002(10) 0.0069(11) 0.0000(9) C3 0.0363(12) 0.0382(11) 0.0523(15) 0.0027(9) 0.0102(10) 0.0015(8) C4 0.0510(16) 0.0672(15) 0.0552(17) -0.0063(12) 0.0102(13) 0.0012(12) C5 0.0314(12) 0.0414(11) 0.0555(14) -0.0002(9) 0.0080(10) -0.0003(9) C6 0.0335(12) 0.0464(11) 0.0504(14) -0.0003(9) 0.0046(10) 0.0003(9) C7 0.0379(13) 0.0468(12) 0.0509(14) 0.0011(10) 0.0070(10) 0.0019(9) C8 0.0462(14) 0.0499(12) 0.0568(15) -0.0054(11) 0.0099(11) 0.0037(10) C9 0.0384(13) 0.0734(16) 0.0510(15) -0.0036(12) 0.0069(11) 0.0038(11) C10 0.0537(16) 0.0732(16) 0.0503(15) 0.0119(12) 0.0068(12) 0.0000(12) C11 0.0505(15) 0.0502(12) 0.0611(16) 0.0059(11) 0.0054(12) -0.0016(10) C12 0.147(3) 0.0483(15) 0.080(2) 0.0106(13) 0.034(2) 0.0157(16) C13 0.077(2) 0.134(3) 0.057(2) -0.0082(17) 0.0226(16) -0.0156(19) C14 0.0363(12) 0.0442(12) 0.0509(14) -0.0020(9) 0.0071(10) 0.0004(9) C15 0.0379(12) 0.0455(11) 0.0394(12) -0.0017(9) 0.0076(9) -0.0036(9) C16 0.0337(12) 0.0532(12) 0.0499(14) -0.0021(10) 0.0048(10) 0.0037(10) C17 0.0446(14) 0.0455(12) 0.0558(15) -0.0046(10) 0.0036(11) 0.0062(10) C18 0.0444(15) 0.0432(13) 0.091(2) -0.0028(11) 0.0038(14) -0.0050(10) C19 0.0348(13) 0.0499(14) 0.099(2) 0.0004(12) 0.0082(13) -0.0017(10) C20 0.0375(15) 0.0674(16) 0.123(3) 0.0050(16) 0.0082(16) -0.0103(12) C21 0.088(2) 0.0447(14) 0.100(2) 0.0036(13) 0.0014(18) 0.0043(14) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 C1 1.637(2) . ? S2 C1 1.718(3) . ? S2 C2 1.744(2) . ? S3 C3 1.727(2) . ? S3 C1 1.745(3) . ? O1 C4 1.208(3) . ? O2 C7 1.371(3) . ? O2 C12 1.406(3) . ? O3 C9 1.371(3) . ? O3 C13 1.428(3) . ? O4 C15 1.368(2) . ? O4 C20 1.430(3) . ? O5 C17 1.368(2) . ? O5 C21 1.419(3) . ? C2 C3 1.355(3) . ? C2 C4 1.459(3) . ? C3 C5 1.520(3) . ? C5 C14 1.528(3) . ? C5 C6 1.528(3) . ? C6 C11 1.390(3) . ? C6 C7 1.395(3) . ? C7 C8 1.377(3) . ? C8 C9 1.385(3) . ? C9 C10 1.383(3) . ? C10 C11 1.378(3) . ? C14 C19 1.374(3) . ? C14 C15 1.396(3) . ? C15 C16 1.384(3) . ? C16 C17 1.385(3) . ? C17 C18 1.368(3) . ? C18 C19 1.387(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 C1 S2 C2 96.80(12) . . ? C3 S3 C1 97.59(11) . . ? C7 O2 C12 117.48(18) . . ? C9 O3 C13 117.2(2) . . ? C15 O4 C20 117.62(17) . . ? C17 O5 C21 117.8(2) . . ? S1 C1 S2 124.47(16) . . ? S1 C1 S3 122.46(16) . . ? S2 C1 S3 113.06(13) . . ? C3 C2 C4 124.4(2) . . ? C3 C2 S2 117.07(18) . . ? C4 C2 S2 118.46(18) . . ? C2 C3 C5 125.9(2) . . ? C2 C3 S3 115.35(17) . . ? C5 C3 S3 118.55(16) . . ? O1 C4 C2 123.6(3) . . ? C3 C5 C14 110.32(16) . . ? C3 C5 C6 110.90(17) . . ? C14 C5 C6 113.72(17) . . ? C11 C6 C7 117.5(2) . . ? C11 C6 C5 123.45(19) . . ? C7 C6 C5 119.05(19) . . ? O2 C7 C8 123.80(19) . . ? O2 C7 C6 115.21(19) . . ? C8 C7 C6 121.0(2) . . ? C7 C8 C9 120.1(2) . . ? O3 C9 C10 125.9(2) . . ? O3 C9 C8 113.9(2) . . ? C10 C9 C8 120.2(2) . . ? C11 C10 C9 119.0(2) . . ? C10 C11 C6 122.2(2) . . ? C19 C14 C15 117.58(19) . . ? C19 C14 C5 122.73(19) . . ? C15 C14 C5 119.69(17) . . ? O4 C15 C16 123.74(19) . . ? O4 C15 C14 115.76(17) . . ? C16 C15 C14 120.50(18) . . ? C15 C16 C17 119.9(2) . . ? O5 C17 C18 124.6(2) . . ? O5 C17 C16 114.6(2) . . ? C18 C17 C16 120.8(2) . . ? C17 C18 C19 118.3(2) . . ? C14 C19 C18 122.9(2) . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 27.53 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.226 _refine_diff_density_min -0.337 _refine_diff_density_rms 0.055