# Supplementary Material (ESI) for New Journal of Chemistry # This journal is (c) The Royal Society of Chemistry and # The Centre National de la Recherche Scientifique, 2008 data_global _journal_coden_Cambridge 440 loop_ _publ_author_name 'John Ripmeester' 'Tara Burchell' 'Gary Enright' _publ_contact_author_name 'John Ripmeester' _publ_contact_author_address ; Steacie Inst. for Molecular Sciences National Research Council Canada 100 Sussex Dr. Ottawa Ontario K1A 0R6 CANADA ; _publ_contact_author_email JOHN.RIPMEESTER@NRC-CNRC.GC.CA _publ_requested_journal 'New Journal of Chemistry' _publ_section_title ; Guest capture, storage and removal in the TATM host framework: A single crystal study ; data_3 _database_code_depnum_ccdc_archive 'CCDC 677778' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '2(C19H16O3S3) 0.50(C3H6O1) 0.39(C2H4Cl2)' _chemical_formula_sum 'C40.28 H36.56 Cl0.78 O6.50 S6' _chemical_formula_weight 844.63 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.036(3) _cell_length_b 10.800(4) _cell_length_c 12.235(5) _cell_angle_alpha 96.582(5) _cell_angle_beta 106.786(5) _cell_angle_gamma 96.366(5) _cell_volume 998.3(7) _cell_formula_units_Z 1 _cell_measurement_temperature 125(2) _cell_measurement_reflns_used 7078 _cell_measurement_theta_min 2.68 _cell_measurement_theta_max 25.20 _exptl_crystal_description plate _exptl_crystal_colour 'pale yellow' _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.405 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 440 _exptl_absorpt_coefficient_mu 0.443 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8713 _exptl_absorpt_correction_T_max 0.9571 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 125(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 'Bruker SMART 1000 CCD' _diffrn_measurement_method '/w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10706 _diffrn_reflns_av_R_equivalents 0.0471 _diffrn_reflns_av_sigmaI/netI 0.0555 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.68 _diffrn_reflns_theta_max 26.37 _reflns_number_total 4055 _reflns_number_gt 3146 _reflns_threshold_expression >2sigma(I) _computing_data_collection SMART _computing_cell_refinement 'SAINT (Bruker 2001)' _computing_data_reduction 'SAINT (Bruker 2001)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _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^)+(0.0033P)^2^+7.9398P] 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 4055 _refine_ls_number_parameters 264 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.1110 _refine_ls_R_factor_gt 0.0877 _refine_ls_wR_factor_ref 0.2103 _refine_ls_wR_factor_gt 0.1982 _refine_ls_goodness_of_fit_ref 1.176 _refine_ls_restrained_S_all 1.175 _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 O1 O 0.0385(7) 0.5760(5) 0.3336(4) 0.0509(14) Uani 1 1 d . . . O2 O 0.4386(6) 0.5327(4) 1.2352(4) 0.0347(10) Uani 1 1 d . . . O3 O 1.1399(5) 1.0672(4) 0.8551(4) 0.0325(10) Uani 1 1 d . . . S1 S 0.0798(2) 0.79738(17) 0.50677(14) 0.0375(4) Uani 1 1 d . . . S2 S 0.24802(18) 0.54073(14) 0.98795(13) 0.0264(3) Uani 1 1 d . . . S3 S 0.91368(18) 0.83029(14) 0.84502(14) 0.0273(4) Uani 1 1 d . . . C1 C 0.4025(6) 0.8243(5) 0.8314(5) 0.0219(11) Uani 1 1 d . . . H1 H 0.3659 0.9035 0.8614 0.026 Uiso 1 1 calc R . . C2 C 0.2942(7) 0.7875(6) 0.7058(5) 0.0254(12) Uani 1 1 d . . . C3 C 0.2986(7) 0.6768(6) 0.6332(5) 0.0256(12) Uani 1 1 d . . . H3 H 0.3704 0.6150 0.6584 0.031 Uiso 1 1 calc R . . C4 C 0.1886(7) 0.6679(6) 0.5227(5) 0.0306(14) Uani 1 1 d . . . C5 C 0.1814(7) 0.8609(6) 0.6486(5) 0.0312(14) Uani 1 1 d . . . H5 H 0.1614 0.9387 0.6836 0.037 Uiso 1 1 calc R . . C6 C 0.1491(8) 0.5683(6) 0.4240(5) 0.0334(14) Uani 1 1 d . . . C7 C 0.2464(8) 0.4562(6) 0.4357(5) 0.0357(15) Uani 1 1 d . . . H7A H 0.1713 0.3818 0.3845 0.054 Uiso 1 1 calc R . . H7B H 0.2768 0.4404 0.5158 0.054 Uiso 1 1 calc R . . H7C H 0.3541 0.4738 0.4142 0.054 Uiso 1 1 calc R . . C8 C 0.3744(7) 0.7265(5) 0.9074(5) 0.0232(12) Uani 1 1 d . . . C9 C 0.4781(7) 0.7358(5) 1.0231(5) 0.0230(12) Uani 1 1 d . . . H9 H 0.5749 0.8008 1.0591 0.028 Uiso 1 1 calc R . . C10 C 0.4274(7) 0.6428(5) 1.0794(5) 0.0232(12) Uani 1 1 d . . . C11 C 0.2442(7) 0.6249(5) 0.8777(5) 0.0251(12) Uani 1 1 d . . . H11 H 0.1599 0.6034 0.8033 0.030 Uiso 1 1 calc R . . C12 C 0.5014(7) 0.6197(6) 1.1973(5) 0.0266(13) Uani 1 1 d . . . C13 C 0.6606(9) 0.7092(7) 1.2738(6) 0.0444(18) Uani 1 1 d . . . H13A H 0.6702 0.7053 1.3550 0.067 Uiso 1 1 calc R . . H13B H 0.6486 0.7953 1.2581 0.067 Uiso 1 1 calc R . . H13C H 0.7664 0.6851 1.2580 0.067 Uiso 1 1 calc R . . C14 C 0.5987(7) 0.8547(5) 0.8418(5) 0.0230(12) Uani 1 1 d . . . C15 C 0.6862(7) 0.9784(5) 0.8490(5) 0.0238(12) Uani 1 1 d . . . H15 H 0.6316 1.0518 0.8521 0.029 Uiso 1 1 calc R . . C16 C 0.8590(7) 0.9806(5) 0.8510(5) 0.0237(12) Uani 1 1 d . . . C17 C 0.7072(7) 0.7663(5) 0.8395(5) 0.0250(12) Uani 1 1 d . . . H17 H 0.6714 0.6786 0.8353 0.030 Uiso 1 1 calc R . . C18 C 0.9921(7) 1.0866(6) 0.8552(5) 0.0277(13) Uani 1 1 d . . . C19 C 0.9416(8) 1.2167(6) 0.8553(6) 0.0359(15) Uani 1 1 d . . . H19A H 1.0479 1.2798 0.8843 0.054 Uiso 1 1 calc R . . H19B H 0.8669 1.2282 0.9053 0.054 Uiso 1 1 calc R . . H19C H 0.8770 1.2269 0.7764 0.054 Uiso 1 1 calc R . . Cl1 Cl 0.2806(9) 0.0993(6) 0.4453(5) 0.0238(14) Uiso 0.27 1 d PD A 1 C21 C 0.4382(18) -0.0029(16) 0.4407(9) 0.016(4) Uiso 0.27 1 d PD . 1 H21A H 0.3777 -0.0904 0.4105 0.019 Uiso 0.27 1 calc PR . 1 H21B H 0.5047 0.0229 0.3882 0.019 Uiso 0.27 1 calc PR . 1 Cl2 Cl 0.327(2) 0.1287(13) 0.4462(10) 0.016(3) Uiso 0.12 1 d PD B 2 C20 C 0.486(9) 0.054(5) 0.538(2) 0.04(2) Uiso 0.12 1 d PD . 2 H20A H 0.5974 0.1135 0.5731 0.047 Uiso 0.12 1 calc PR . 2 H20B H 0.4433 0.0255 0.5998 0.047 Uiso 0.12 1 calc PR . 2 O4 O 0.604(3) 0.150(2) 0.632(2) 0.059(6) Uiso 0.25 1 d P C -3 C30 C 0.524(5) 0.070(3) 0.549(3) 0.047(12) Uiso 0.25 1 d PD C -3 C31 C 0.374(5) 0.095(5) 0.447(3) 0.057(11) Uiso 0.25 1 d PD C -3 H31A H 0.3434 0.1791 0.4658 0.086 Uiso 0.25 1 calc PR C -3 H31B H 0.2704 0.0314 0.4333 0.086 Uiso 0.25 1 calc PR C -3 H31C H 0.4110 0.0924 0.3775 0.086 Uiso 0.25 1 calc PR C -3 C31A C 0.579(6) -0.061(3) 0.527(4) 0.061(10) Uiso 0.25 1 d PD C -3 H31D H 0.6728 -0.0727 0.5950 0.092 Uiso 0.25 1 calc PR C -3 H31E H 0.6208 -0.0666 0.4595 0.092 Uiso 0.25 1 calc PR C -3 H31F H 0.4772 -0.1263 0.5136 0.092 Uiso 0.25 1 calc PR C -3 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.051(3) 0.049(3) 0.031(3) 0.002(2) -0.013(2) -0.008(2) O2 0.031(2) 0.033(2) 0.039(3) 0.008(2) 0.012(2) -0.0021(19) O3 0.015(2) 0.037(2) 0.041(3) -0.0051(19) 0.0095(18) -0.0055(17) S1 0.0253(8) 0.0479(10) 0.0296(8) 0.0056(7) -0.0037(6) -0.0018(7) S2 0.0171(7) 0.0270(7) 0.0322(8) -0.0016(6) 0.0071(6) -0.0018(5) S3 0.0132(6) 0.0305(8) 0.0382(8) 0.0015(6) 0.0096(6) 0.0029(5) C1 0.009(2) 0.029(3) 0.025(3) 0.000(2) 0.002(2) 0.003(2) C2 0.008(2) 0.036(3) 0.030(3) 0.004(2) 0.005(2) -0.001(2) C3 0.014(3) 0.033(3) 0.026(3) 0.003(2) 0.003(2) 0.000(2) C4 0.017(3) 0.039(3) 0.033(3) 0.008(3) 0.007(2) -0.006(2) C5 0.017(3) 0.039(3) 0.032(3) 0.001(3) 0.004(2) -0.002(2) C6 0.029(3) 0.038(4) 0.024(3) 0.002(3) 0.002(3) -0.011(3) C7 0.028(3) 0.046(4) 0.028(3) -0.004(3) 0.006(3) 0.002(3) C8 0.009(2) 0.030(3) 0.031(3) 0.001(2) 0.006(2) 0.005(2) C9 0.012(2) 0.030(3) 0.025(3) -0.003(2) 0.006(2) 0.002(2) C10 0.013(2) 0.026(3) 0.031(3) -0.001(2) 0.009(2) 0.003(2) C11 0.014(3) 0.030(3) 0.027(3) -0.006(2) 0.005(2) 0.001(2) C12 0.015(3) 0.033(3) 0.031(3) 0.000(3) 0.008(2) 0.004(2) C13 0.028(3) 0.062(5) 0.029(4) 0.012(3) -0.006(3) -0.017(3) C14 0.012(2) 0.032(3) 0.022(3) -0.001(2) 0.005(2) -0.002(2) C15 0.017(3) 0.030(3) 0.023(3) 0.000(2) 0.005(2) 0.005(2) C16 0.016(3) 0.026(3) 0.026(3) -0.002(2) 0.005(2) 0.000(2) C17 0.016(3) 0.026(3) 0.032(3) 0.000(2) 0.010(2) 0.003(2) C18 0.022(3) 0.033(3) 0.024(3) -0.002(2) 0.006(2) -0.002(2) C19 0.029(3) 0.031(3) 0.047(4) 0.000(3) 0.013(3) 0.002(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 O1 C6 1.220(8) . ? O2 C12 1.217(7) . ? O3 C18 1.228(7) . ? S1 C5 1.713(6) . ? S1 C4 1.729(7) . ? S2 C11 1.706(6) . ? S2 C10 1.726(6) . ? S3 C17 1.705(6) . ? S3 C16 1.727(6) . ? C1 C2 1.512(8) . ? C1 C8 1.525(8) . ? C1 C14 1.539(7) . ? C2 C5 1.364(9) . ? C2 C3 1.416(8) . ? C3 C4 1.371(8) . ? C4 C6 1.456(9) . ? C6 C7 1.511(10) . ? C8 C11 1.365(8) . ? C8 C9 1.406(8) . ? C9 C10 1.371(8) . ? C10 C12 1.454(8) . ? C12 C13 1.508(8) . ? C14 C17 1.366(8) . ? C14 C15 1.420(8) . ? C15 C16 1.379(8) . ? C16 C18 1.463(8) . ? C18 C19 1.506(9) . ? Cl1 C21 1.778(9) . ? C21 C21 1.493(18) 2_656 ? Cl2 C20 1.770(10) . ? C20 C20 1.49(2) 2_656 ? O4 C30 1.23(4) . ? C30 C31A 1.538(10) . ? C30 C31 1.539(10) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C5 S1 C4 91.3(3) . . ? C11 S2 C10 91.3(3) . . ? C17 S3 C16 91.7(3) . . ? C2 C1 C8 113.9(5) . . ? C2 C1 C14 110.2(4) . . ? C8 C1 C14 110.6(4) . . ? C5 C2 C3 112.0(5) . . ? C5 C2 C1 122.7(6) . . ? C3 C2 C1 125.3(5) . . ? C4 C3 C2 113.0(6) . . ? C3 C4 C6 130.4(6) . . ? C3 C4 S1 111.1(5) . . ? C6 C4 S1 118.5(5) . . ? C2 C5 S1 112.6(5) . . ? O1 C6 C4 120.0(7) . . ? O1 C6 C7 121.0(6) . . ? C4 C6 C7 119.1(5) . . ? C11 C8 C9 110.9(5) . . ? C11 C8 C1 126.5(5) . . ? C9 C8 C1 122.5(5) . . ? C10 C9 C8 114.1(5) . . ? C9 C10 C12 130.5(5) . . ? C9 C10 S2 110.4(4) . . ? C12 C10 S2 119.1(4) . . ? C8 C11 S2 113.2(4) . . ? O2 C12 C10 122.4(5) . . ? O2 C12 C13 120.0(6) . . ? C10 C12 C13 117.6(5) . . ? C17 C14 C15 111.9(5) . . ? C17 C14 C1 124.4(5) . . ? C15 C14 C1 123.6(5) . . ? C16 C15 C14 112.8(5) . . ? C15 C16 C18 130.2(5) . . ? C15 C16 S3 110.9(4) . . ? C18 C16 S3 118.9(4) . . ? C14 C17 S3 112.8(4) . . ? O3 C18 C16 119.6(6) . . ? O3 C18 C19 121.7(5) . . ? C16 C18 C19 118.6(5) . . ? C21 C21 Cl1 109.5(11) 2_656 . ? C20 C20 Cl2 105.9(17) 2_656 . ? O4 C30 C31A 124(3) . . ? O4 C30 C31 123(3) . . ? C31A C30 C31 113(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 C8 C1 C2 C5 123.6(6) . . . . ? C14 C1 C2 C5 -111.4(6) . . . . ? C8 C1 C2 C3 -57.7(7) . . . . ? C14 C1 C2 C3 67.3(7) . . . . ? C5 C2 C3 C4 -0.3(7) . . . . ? C1 C2 C3 C4 -179.2(5) . . . . ? C2 C3 C4 C6 -177.2(6) . . . . ? C2 C3 C4 S1 0.6(6) . . . . ? C5 S1 C4 C3 -0.6(5) . . . . ? C5 S1 C4 C6 177.6(5) . . . . ? C3 C2 C5 S1 -0.1(6) . . . . ? C1 C2 C5 S1 178.8(4) . . . . ? C4 S1 C5 C2 0.4(5) . . . . ? C3 C4 C6 O1 176.0(6) . . . . ? S1 C4 C6 O1 -1.7(8) . . . . ? C3 C4 C6 C7 -3.8(10) . . . . ? S1 C4 C6 C7 178.5(5) . . . . ? C2 C1 C8 C11 -12.1(8) . . . . ? C14 C1 C8 C11 -136.8(6) . . . . ? C2 C1 C8 C9 172.0(5) . . . . ? C14 C1 C8 C9 47.3(7) . . . . ? C11 C8 C9 C10 0.2(7) . . . . ? C1 C8 C9 C10 176.7(5) . . . . ? C8 C9 C10 C12 179.3(5) . . . . ? C8 C9 C10 S2 0.2(6) . . . . ? C11 S2 C10 C9 -0.5(4) . . . . ? C11 S2 C10 C12 -179.6(5) . . . . ? C9 C8 C11 S2 -0.6(6) . . . . ? C1 C8 C11 S2 -176.8(4) . . . . ? C10 S2 C11 C8 0.6(4) . . . . ? C9 C10 C12 O2 179.0(6) . . . . ? S2 C10 C12 O2 -2.1(8) . . . . ? C9 C10 C12 C13 -0.4(9) . . . . ? S2 C10 C12 C13 178.6(5) . . . . ? C2 C1 C14 C17 -82.0(7) . . . . ? C8 C1 C14 C17 44.8(7) . . . . ? C2 C1 C14 C15 94.6(6) . . . . ? C8 C1 C14 C15 -138.6(5) . . . . ? C17 C14 C15 C16 0.5(7) . . . . ? C1 C14 C15 C16 -176.5(5) . . . . ? C14 C15 C16 C18 178.4(6) . . . . ? C14 C15 C16 S3 -0.4(6) . . . . ? C17 S3 C16 C15 0.1(5) . . . . ? C17 S3 C16 C18 -178.8(5) . . . . ? C15 C14 C17 S3 -0.4(6) . . . . ? C1 C14 C17 S3 176.6(4) . . . . ? C16 S3 C17 C14 0.1(5) . . . . ? C15 C16 C18 O3 -179.2(6) . . . . ? S3 C16 C18 O3 -0.5(8) . . . . ? C15 C16 C18 C19 -1.2(9) . . . . ? S3 C16 C18 C19 177.4(5) . . . . ? H1 C1 C2 C5 5.1 . . . . ? H1 C1 C8 C11 106.5 . . . . ? H1 C1 C14 C17 161.5 . . . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 26.37 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.920 _refine_diff_density_min -0.850 _refine_diff_density_rms 0.109 data_dc-ace-0-100 _database_code_depnum_ccdc_archive 'CCDC 677779' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '2(C19H16O3S3) 1.0(C3H6O1)' _chemical_formula_sum 'C41 H38 O7 S6' _chemical_formula_weight 835.07 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 8.1164(16) _cell_length_b 10.570(2) _cell_length_c 12.351(3) _cell_angle_alpha 95.006(7) _cell_angle_beta 107.786(6) _cell_angle_gamma 95.944(6) _cell_volume 995.6(3) _cell_formula_units_Z 1 _cell_measurement_temperature 100(1) _cell_measurement_reflns_used 3784 _cell_measurement_theta_min 2.68 _cell_measurement_theta_max 29.86 _exptl_crystal_description block _exptl_crystal_colour 'pale yellow' _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.393 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 436 _exptl_absorpt_coefficient_mu 0.393 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9398 _exptl_absorpt_correction_T_max 0.9434 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 'Bruker Kappa APEXII CCD' _diffrn_measurement_method ' \f & \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13911 _diffrn_reflns_av_R_equivalents 0.0534 _diffrn_reflns_av_sigmaI/netI 0.0635 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.66 _diffrn_reflns_theta_max 26.37 _reflns_number_total 4005 _reflns_number_gt 2968 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker, 2006)' _computing_cell_refinement 'SAINT (Bruker, 2006)' _computing_data_reduction 'SAINT (Bruker, 2006)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _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^)+(0.0917P)^2^+0.5034P] 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 4005 _refine_ls_number_parameters 289 _refine_ls_number_restraints 176 _refine_ls_R_factor_all 0.0829 _refine_ls_R_factor_gt 0.0597 _refine_ls_wR_factor_ref 0.1612 _refine_ls_wR_factor_gt 0.1437 _refine_ls_goodness_of_fit_ref 1.043 _refine_ls_restrained_S_all 1.079 _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 O1 O 0.9418(3) 0.0362(2) 0.73837(19) 0.0364(6) Uani 1 1 d U . . O2 O 1.6399(3) 0.5663(2) 0.35678(19) 0.0351(6) Uani 1 1 d U . . O3 O 0.5229(3) 0.0802(3) -0.1625(2) 0.0520(7) Uani 1 1 d U . . S1 S 0.75423(9) 0.04116(8) 0.48917(6) 0.0283(2) Uani 1 1 d U . . S2 S 1.40905(9) 0.32719(8) 0.34028(7) 0.0296(2) Uani 1 1 d U . . S3 S 0.56927(10) 0.30670(10) 0.00741(7) 0.0398(3) Uani 1 1 d U . . C1 C 0.9057(3) 0.3300(3) 0.3294(2) 0.0258(7) Uani 1 1 d U . . H1 H 0.8720 0.4115 0.3583 0.031 Uiso 1 1 calc R . . C2 C 0.8778(3) 0.2299(3) 0.4060(2) 0.0247(6) Uani 1 1 d U . . C3 C 0.9802(3) 0.2406(3) 0.5226(3) 0.0253(7) Uani 1 1 d U . . C4 C 0.9287(3) 0.1458(3) 0.5795(2) 0.0252(7) Uani 1 1 d U . . C5 C 0.7508(4) 0.1264(3) 0.3763(3) 0.0277(7) Uani 1 1 d U . . C6 C 1.0029(4) 0.1254(3) 0.7004(3) 0.0296(7) Uani 1 1 d U . . C7 C 1.1578(5) 0.2178(4) 0.7749(3) 0.0455(10) Uani 1 1 d U . . H7A H 1.1709 0.2114 0.8557 0.068 Uiso 1 1 calc R . . H7B H 1.1399 0.3054 0.7587 0.068 Uiso 1 1 calc R . . H7C H 1.2635 0.1968 0.7588 0.068 Uiso 1 1 calc R . . C8 C 1.0981(3) 0.3565(3) 0.3380(2) 0.0247(6) Uani 1 1 d U . . C9 C 1.1878(4) 0.4822(3) 0.3479(2) 0.0259(7) Uani 1 1 d U . . C10 C 1.3590(4) 0.4805(3) 0.3495(2) 0.0259(7) Uani 1 1 d U . . C11 C 1.2030(4) 0.2647(3) 0.3340(3) 0.0273(7) Uani 1 1 d U . . C12 C 1.4928(4) 0.5881(3) 0.3561(2) 0.0283(7) Uani 1 1 d U . . C13 C 1.4459(4) 0.7201(4) 0.3593(3) 0.0377(8) Uani 1 1 d U . . H13A H 1.5526 0.7822 0.3860 0.056 Uiso 1 1 calc R . . H13B H 1.3775 0.7310 0.4117 0.056 Uiso 1 1 calc R . . H13C H 1.3765 0.7343 0.2822 0.056 Uiso 1 1 calc R . . C14 C 0.7933(3) 0.2945(3) 0.2045(3) 0.0273(7) Uani 1 1 d U . . C15 C 0.7967(4) 0.1823(3) 0.1325(3) 0.0286(7) Uani 1 1 d U . . C16 C 0.6813(4) 0.1755(3) 0.0237(3) 0.0319(7) Uani 1 1 d U . . C17 C 0.6768(4) 0.3699(4) 0.1470(3) 0.0328(8) Uani 1 1 d U . . C18 C 0.6407(4) 0.0745(4) -0.0740(3) 0.0372(8) Uani 1 1 d U . . C19 C 0.7455(5) -0.0349(4) -0.0636(3) 0.0435(9) Uani 1 1 d U . . H19A H 0.6700 -0.1135 -0.1057 0.065 Uiso 1 1 calc R . . H19B H 0.7943 -0.0463 0.0174 0.065 Uiso 1 1 calc R . . H19C H 0.8406 -0.0167 -0.0957 0.065 Uiso 1 1 calc R . . H3 H 1.066(4) 0.306(3) 0.555(3) 0.022(8) Uiso 1 1 d . . . H5 H 0.664(5) 0.091(4) 0.301(3) 0.043(10) Uiso 1 1 d . . . H9 H 1.139(4) 0.552(3) 0.351(2) 0.011(7) Uiso 1 1 d . . . H11 H 1.179(4) 0.174(3) 0.331(2) 0.022(8) Uiso 1 1 d . . . H15 H 0.859(4) 0.114(3) 0.154(2) 0.014(7) Uiso 1 1 d . . . H17 H 0.648(5) 0.442(4) 0.176(3) 0.033(10) Uiso 1 1 d . . . O4 O 0.8966(7) 0.3467(6) 0.8714(5) 0.0586(15) Uani 0.50 1 d PU A -1 C20 C 0.9730(9) 0.4237(7) 0.9520(6) 0.0406(17) Uani 0.50 1 d PDU A -1 C21 C 1.1296(11) 0.3915(11) 1.0448(8) 0.053(2) Uani 0.50 1 d PDU A -1 H21A H 1.1483 0.3032 1.0261 0.080 Uiso 0.50 1 calc PR A -1 H21B H 1.1077 0.4001 1.1187 0.080 Uiso 0.50 1 calc PR A -1 H21C H 1.2337 0.4504 1.0495 0.080 Uiso 0.50 1 calc PR A -1 C22 C 0.9171(12) 0.5552(8) 0.9646(8) 0.046(2) Uani 0.50 1 d PDU A -1 H22A H 0.8149 0.5618 0.8990 0.069 Uiso 0.50 1 calc PR A -1 H22B H 1.0130 0.6211 0.9674 0.069 Uiso 0.50 1 calc PR A -1 H22C H 0.8871 0.5676 1.0356 0.069 Uiso 0.50 1 calc PR A -1 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0305(11) 0.0363(15) 0.0417(12) 0.0075(10) 0.0133(9) -0.0067(10) O2 0.0163(10) 0.0386(15) 0.0489(13) -0.0024(10) 0.0134(9) -0.0060(9) O3 0.0462(15) 0.0549(18) 0.0376(13) 0.0015(11) -0.0038(11) -0.0142(13) S1 0.0155(3) 0.0291(5) 0.0375(4) -0.0005(3) 0.0093(3) -0.0079(3) S2 0.0129(3) 0.0314(5) 0.0436(5) 0.0020(3) 0.0104(3) -0.0032(3) S3 0.0226(4) 0.0487(6) 0.0388(5) 0.0077(4) -0.0014(3) -0.0053(4) C1 0.0119(12) 0.0304(18) 0.0335(15) 0.0020(12) 0.0070(11) -0.0018(11) C2 0.0126(12) 0.0273(18) 0.0345(15) 0.0009(12) 0.0095(11) 0.0009(11) C3 0.0103(12) 0.0306(18) 0.0334(15) -0.0015(12) 0.0080(11) -0.0036(12) C4 0.0098(11) 0.0303(18) 0.0345(15) -0.0005(12) 0.0090(10) -0.0035(11) C5 0.0162(13) 0.0327(19) 0.0324(15) 0.0011(12) 0.0083(11) -0.0041(12) C6 0.0185(13) 0.0316(19) 0.0382(16) 0.0026(13) 0.0107(12) -0.0034(12) C7 0.0330(17) 0.056(2) 0.0366(17) 0.0089(15) 0.0031(13) -0.0198(16) C8 0.0134(12) 0.0302(18) 0.0273(14) 0.0001(11) 0.0054(10) -0.0051(11) C9 0.0148(12) 0.0289(19) 0.0323(15) 0.0006(12) 0.0072(11) -0.0012(12) C10 0.0163(12) 0.0288(18) 0.0301(14) -0.0001(11) 0.0069(11) -0.0039(12) C11 0.0153(13) 0.0298(19) 0.0362(15) 0.0035(12) 0.0095(11) -0.0034(12) C12 0.0192(13) 0.0300(18) 0.0321(15) -0.0013(12) 0.0072(11) -0.0053(12) C13 0.0266(15) 0.033(2) 0.0507(19) 0.0005(14) 0.0137(14) -0.0085(14) C14 0.0104(12) 0.0345(19) 0.0353(15) 0.0030(12) 0.0082(11) -0.0063(11) C15 0.0131(12) 0.035(2) 0.0353(15) 0.0044(13) 0.0078(11) -0.0056(12) C16 0.0207(14) 0.038(2) 0.0350(16) 0.0030(13) 0.0099(12) -0.0081(13) C17 0.0189(14) 0.037(2) 0.0389(17) 0.0041(14) 0.0064(12) -0.0036(13) C18 0.0275(15) 0.045(2) 0.0337(16) 0.0027(14) 0.0102(13) -0.0178(14) C19 0.0359(18) 0.053(2) 0.0392(17) -0.0048(15) 0.0161(14) -0.0072(16) O4 0.046(3) 0.061(4) 0.059(3) -0.002(2) 0.005(2) 0.003(3) C20 0.037(3) 0.048(4) 0.036(3) 0.001(3) 0.016(3) -0.002(3) C21 0.052(4) 0.057(5) 0.049(4) 0.009(4) 0.015(3) 0.006(4) C22 0.047(4) 0.050(4) 0.047(4) 0.003(3) 0.024(3) 0.002(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 O1 C6 1.216(4) . ? O2 C12 1.236(4) . ? O3 C18 1.224(4) . ? S1 C5 1.720(3) . ? S1 C4 1.723(3) . ? S2 C11 1.709(3) . ? S2 C10 1.714(3) . ? S3 C17 1.715(3) . ? S3 C16 1.729(4) . ? C1 C14 1.523(4) . ? C1 C2 1.524(4) . ? C1 C8 1.527(4) . ? C1 H1 1.0000 . ? C2 C5 1.363(4) . ? C2 C3 1.413(4) . ? C3 C4 1.374(4) . ? C3 H3 0.90(3) . ? C4 C6 1.474(4) . ? C5 H5 0.99(4) . ? C6 C7 1.504(4) . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C8 C11 1.363(5) . ? C8 C9 1.423(4) . ? C9 C10 1.386(4) . ? C9 H9 0.87(3) . ? C10 C12 1.468(4) . ? C11 H11 0.95(3) . ? C12 C13 1.484(5) . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C14 C17 1.371(5) . ? C14 C15 1.426(5) . ? C15 C16 1.375(4) . ? C15 H15 0.94(3) . ? C16 C18 1.470(5) . ? C17 H17 0.90(4) . ? C18 C19 1.496(6) . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? O4 C20 1.191(9) . ? C20 C22 1.515(8) . ? C20 C21 1.521(8) . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? 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 C5 S1 C4 91.32(15) . . ? C11 S2 C10 91.59(15) . . ? C17 S3 C16 91.15(17) . . ? C14 C1 C2 113.3(2) . . ? C14 C1 C8 110.1(2) . . ? C2 C1 C8 110.9(2) . . ? C14 C1 H1 107.4 . . ? C2 C1 H1 107.4 . . ? C8 C1 H1 107.4 . . ? C5 C2 C3 111.8(3) . . ? C5 C2 C1 126.4(3) . . ? C3 C2 C1 121.7(3) . . ? C4 C3 C2 113.3(3) . . ? C4 C3 H3 125(2) . . ? C2 C3 H3 122(2) . . ? C3 C4 C6 128.9(3) . . ? C3 C4 S1 111.1(2) . . ? C6 C4 S1 120.0(2) . . ? C2 C5 S1 112.5(2) . . ? C2 C5 H5 131(2) . . ? S1 C5 H5 116(2) . . ? O1 C6 C4 121.0(3) . . ? O1 C6 C7 121.1(3) . . ? C4 C6 C7 117.8(3) . . ? C6 C7 H7A 109.5 . . ? C6 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C6 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C11 C8 C9 111.9(3) . . ? C11 C8 C1 124.9(3) . . ? C9 C8 C1 123.2(3) . . ? C10 C9 C8 112.1(3) . . ? C10 C9 H9 124(2) . . ? C8 C9 H9 123.5(19) . . ? C9 C10 C12 129.2(3) . . ? C9 C10 S2 111.6(2) . . ? C12 C10 S2 119.2(2) . . ? C8 C11 S2 112.8(2) . . ? C8 C11 H11 129.8(19) . . ? S2 C11 H11 117.3(19) . . ? O2 C12 C10 119.3(3) . . ? O2 C12 C13 122.0(3) . . ? C10 C12 C13 118.7(3) . . ? C12 C13 H13A 109.5 . . ? C12 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C12 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C17 C14 C15 111.6(3) . . ? C17 C14 C1 123.0(3) . . ? C15 C14 C1 125.4(3) . . ? C16 C15 C14 112.6(3) . . ? C16 C15 H15 120.2(18) . . ? C14 C15 H15 126.9(17) . . ? C15 C16 C18 129.6(3) . . ? C15 C16 S3 111.7(3) . . ? C18 C16 S3 118.7(3) . . ? C14 C17 S3 112.9(3) . . ? C14 C17 H17 127(2) . . ? S3 C17 H17 120(2) . . ? O3 C18 C16 120.3(4) . . ? O3 C18 C19 120.6(3) . . ? C16 C18 C19 119.1(3) . . ? C18 C19 H19A 109.5 . . ? C18 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C18 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? O4 C20 C22 121.1(7) . . ? O4 C20 C21 120.2(8) . . ? C22 C20 C21 118.7(9) . . ? C20 C21 H21A 109.5 . . ? C20 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C20 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C20 C22 H22A 109.5 . . ? C20 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C20 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? 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 C14 C1 C2 C5 -9.3(4) . . . . ? C8 C1 C2 C5 -133.7(3) . . . . ? C14 C1 C2 C3 174.8(3) . . . . ? C8 C1 C2 C3 50.4(4) . . . . ? C5 C2 C3 C4 -0.4(4) . . . . ? C1 C2 C3 C4 176.1(3) . . . . ? C2 C3 C4 C6 180.0(3) . . . . ? C2 C3 C4 S1 0.6(3) . . . . ? C5 S1 C4 C3 -0.5(3) . . . . ? C5 S1 C4 C6 -180.0(3) . . . . ? C3 C2 C5 S1 0.0(4) . . . . ? C1 C2 C5 S1 -176.3(2) . . . . ? C4 S1 C5 C2 0.3(3) . . . . ? C3 C4 C6 O1 179.8(3) . . . . ? S1 C4 C6 O1 -0.8(4) . . . . ? C3 C4 C6 C7 -0.8(5) . . . . ? S1 C4 C6 C7 178.6(3) . . . . ? C14 C1 C8 C11 -80.3(4) . . . . ? C2 C1 C8 C11 45.9(4) . . . . ? C14 C1 C8 C9 97.8(3) . . . . ? C2 C1 C8 C9 -136.0(3) . . . . ? C11 C8 C9 C10 0.9(4) . . . . ? C1 C8 C9 C10 -177.5(3) . . . . ? C8 C9 C10 C12 178.5(3) . . . . ? C8 C9 C10 S2 -0.6(3) . . . . ? C11 S2 C10 C9 0.1(2) . . . . ? C11 S2 C10 C12 -179.1(2) . . . . ? C9 C8 C11 S2 -0.7(3) . . . . ? C1 C8 C11 S2 177.5(2) . . . . ? C10 S2 C11 C8 0.3(2) . . . . ? C9 C10 C12 O2 179.8(3) . . . . ? S2 C10 C12 O2 -1.2(4) . . . . ? C9 C10 C12 C13 -1.5(5) . . . . ? S2 C10 C12 C13 177.6(2) . . . . ? C2 C1 C14 C17 121.6(3) . . . . ? C8 C1 C14 C17 -113.6(3) . . . . ? C2 C1 C14 C15 -59.5(4) . . . . ? C8 C1 C14 C15 65.3(4) . . . . ? C17 C14 C15 C16 -0.8(4) . . . . ? C1 C14 C15 C16 -179.9(3) . . . . ? C14 C15 C16 C18 -177.6(3) . . . . ? C14 C15 C16 S3 0.7(3) . . . . ? C17 S3 C16 C15 -0.3(2) . . . . ? C17 S3 C16 C18 178.2(2) . . . . ? C15 C14 C17 S3 0.6(3) . . . . ? C1 C14 C17 S3 179.7(2) . . . . ? C16 S3 C17 C14 -0.2(2) . . . . ? C15 C16 C18 O3 174.1(3) . . . . ? S3 C16 C18 O3 -4.1(4) . . . . ? C15 C16 C18 C19 -6.0(5) . . . . ? S3 C16 C18 C19 175.8(2) . . . . ? H1 C1 C14 C17 3.1 . . . . ? H1 C1 C8 C11 163.0 . . . . ? H1 C1 C2 C5 109.2 . . . . ? _diffrn_measured_fraction_theta_max 0.982 _diffrn_reflns_theta_full 26.37 _diffrn_measured_fraction_theta_full 0.982 _refine_diff_density_max 0.751 _refine_diff_density_min -0.706 _refine_diff_density_rms 0.097 data_dce-ace-40-60 _database_code_depnum_ccdc_archive 'CCDC 677780' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '2(C19H16O3S3) 0.40(C2H4Cl2) 0.60(C3H6O1)' _chemical_formula_sum 'C40.60 H37.20 Cl0.80 O6.60 S6' _chemical_formula_weight 851.42 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 '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 7.9717(6) _cell_length_b 10.8775(7) _cell_length_c 12.1307(9) _cell_angle_alpha 97.149(4) _cell_angle_beta 106.072(4) _cell_angle_gamma 96.567(4) _cell_volume 990.62(12) _cell_formula_units_Z 1 _cell_measurement_temperature 100(1) _cell_measurement_reflns_used 5564 _cell_measurement_theta_min 2.75 _cell_measurement_theta_max 32.50 _exptl_crystal_description block _exptl_crystal_colour 'pale yellow' _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.427 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 443 _exptl_absorpt_coefficient_mu 0.448 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8699 _exptl_absorpt_correction_T_max 0.9157 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 95(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 'Bruker Kappa APEXII CCD' _diffrn_measurement_method ' \f & \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13226 _diffrn_reflns_av_R_equivalents 0.0325 _diffrn_reflns_av_sigmaI/netI 0.0494 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.69 _diffrn_reflns_theta_max 30.51 _reflns_number_total 5736 _reflns_number_gt 4448 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker, 2006)' _computing_cell_refinement 'SAINT (Bruker, 2006)' _computing_data_reduction 'SAINT (Bruker, 2006)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _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^)+(0.0638P)^2^+0.7403P] 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 5736 _refine_ls_number_parameters 309 _refine_ls_number_restraints 34 _refine_ls_R_factor_all 0.0655 _refine_ls_R_factor_gt 0.0478 _refine_ls_wR_factor_ref 0.1314 _refine_ls_wR_factor_gt 0.1193 _refine_ls_goodness_of_fit_ref 1.039 _refine_ls_restrained_S_all 1.041 _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 O1 O 0.36029(19) -0.06885(14) 0.14556(14) 0.0218(3) Uani 1 1 d . . . O2 O 1.0596(2) 0.47111(15) -0.23517(15) 0.0238(3) Uani 1 1 d . . . O3 O 1.4517(2) 0.42538(17) 0.67002(15) 0.0324(4) Uani 1 1 d . . . S1 S 0.58591(6) 0.16765(5) 0.15485(5) 0.01662(12) Uani 1 1 d . . . S2 S 1.25582(6) 0.45961(4) 0.01046(4) 0.01617(12) Uani 1 1 d . . . S3 S 1.41296(7) 0.20458(5) 0.49401(5) 0.02138(13) Uani 1 1 d . . . C1 C 1.0980(2) 0.17730(18) 0.16586(17) 0.0140(4) Uani 1 1 d . . . H1 H 1.1356 0.0987 0.1352 0.017 Uiso 1 1 calc R . . C2 C 0.9033(2) 0.14584(18) 0.15672(16) 0.0131(3) Uani 1 1 d . . . C3 C 0.8155(3) 0.02288(19) 0.14888(17) 0.0148(4) Uani 1 1 d . . . C4 C 0.6423(3) 0.01980(18) 0.14768(17) 0.0146(4) Uani 1 1 d . . . C5 C 0.7934(3) 0.23293(19) 0.15979(18) 0.0157(4) Uani 1 1 d . . . C6 C 0.5092(3) -0.08645(19) 0.14442(18) 0.0172(4) Uani 1 1 d . . . C7 C 0.5612(3) -0.2144(2) 0.1436(2) 0.0243(5) Uani 1 1 d . . . H7A H 0.6245 -0.2240 0.2230 0.036 Uiso 1 1 calc R . . H7B H 0.6383 -0.2248 0.0937 0.036 Uiso 1 1 calc R . . H7C H 0.4551 -0.2780 0.1136 0.036 Uiso 1 1 calc R . . C8 C 1.1278(2) 0.27407(18) 0.09042(17) 0.0136(4) Uani 1 1 d . . . C9 C 1.0203(2) 0.26612(18) -0.02540(17) 0.0136(4) Uani 1 1 d . . . C10 C 1.0725(2) 0.36044(18) -0.08025(17) 0.0137(4) Uani 1 1 d . . . C11 C 1.2607(3) 0.37528(19) 0.12078(18) 0.0163(4) Uani 1 1 d . . . C12 C 0.9943(3) 0.38341(19) -0.19800(18) 0.0172(4) Uani 1 1 d . . . C13 C 0.8312(3) 0.2978(2) -0.2732(2) 0.0291(5) Uani 1 1 d . . . H13A H 0.7264 0.3337 -0.2665 0.044 Uiso 1 1 calc R . . H13B H 0.8278 0.2156 -0.2479 0.044 Uiso 1 1 calc R . . H13C H 0.8326 0.2881 -0.3543 0.044 Uiso 1 1 calc R . . C14 C 1.2056(2) 0.21458(19) 0.29230(17) 0.0154(4) Uani 1 1 d . . . C15 C 1.2010(3) 0.3260(2) 0.36565(18) 0.0165(4) Uani 1 1 d . . . C16 C 1.3071(3) 0.3340(2) 0.47761(18) 0.0179(4) Uani 1 1 d . . . C17 C 1.3150(3) 0.1412(2) 0.35120(18) 0.0184(4) Uani 1 1 d . . . C18 C 1.3464(3) 0.4348(2) 0.57776(19) 0.0215(4) Uani 1 1 d . . . C19 C 1.2541(3) 0.5468(2) 0.5654(2) 0.0255(5) Uani 1 1 d . . . H19A H 1.1545 0.5374 0.5978 0.038 Uiso 1 1 calc R . . H19B H 1.2103 0.5537 0.4829 0.038 Uiso 1 1 calc R . . H19C H 1.3370 0.6226 0.6073 0.038 Uiso 1 1 calc R . . H3 H 0.866(3) -0.047(2) 0.144(2) 0.017(6) Uiso 1 1 d . . . H5 H 0.822(3) 0.322(2) 0.163(2) 0.019(6) Uiso 1 1 d . . . H9 H 0.923(3) 0.201(2) -0.060(2) 0.021(6) Uiso 1 1 d . . . H11 H 1.352(3) 0.398(2) 0.193(2) 0.016(6) Uiso 1 1 d . . . H15 H 1.140(3) 0.389(2) 0.340(2) 0.017(6) Uiso 1 1 d . . . H17 H 1.330(4) 0.061(3) 0.324(3) 0.030(7) Uiso 1 1 d . . . O4 O 0.9248(10) 0.8611(7) 0.3606(7) 0.0479(18) Uani 0.30 1 d PU A -1 C20 C 0.9963(9) 0.9362(7) 0.4546(7) 0.0190(13) Uani 0.30 1 d PDU A -1 C21 C 0.9211(15) 1.0602(9) 0.4710(11) 0.039(2) Uani 0.30 1 d PDU A -1 H21A H 0.8347 1.0683 0.3981 0.059 Uiso 0.30 1 calc PR A -1 H21B H 1.0176 1.1313 0.4927 0.059 Uiso 0.30 1 calc PR A -1 H21C H 0.8633 1.0593 0.5325 0.059 Uiso 0.30 1 calc PR A -1 C22 C 1.1407(14) 0.8943(13) 0.5481(10) 0.037(3) Uani 0.30 1 d PDU A -1 H22A H 1.1668 0.8134 0.5173 0.056 Uiso 0.30 1 calc PR A -1 H22B H 1.0998 0.8857 0.6162 0.056 Uiso 0.30 1 calc PR A -1 H22C H 1.2478 0.9570 0.5705 0.056 Uiso 0.30 1 calc PR A -1 C31 C 0.9423(8) 0.9981(7) 0.4402(5) 0.0351(15) Uani 0.40 1 d PDU . 2 H31A H 0.8768 0.9123 0.4082 0.042 Uiso 0.40 1 calc PR . 2 H31B H 1.0147 1.0214 0.3893 0.042 Uiso 0.40 1 calc PR . 2 Cl1 Cl 0.7903(3) 1.1064(2) 0.44482(17) 0.0335(4) Uani 0.40 1 d PD B 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0159(7) 0.0219(8) 0.0270(8) -0.0009(6) 0.0094(6) -0.0021(6) O2 0.0278(8) 0.0203(8) 0.0244(8) 0.0071(6) 0.0092(6) 0.0005(6) O3 0.0353(10) 0.0346(10) 0.0176(8) -0.0002(7) -0.0037(7) -0.0009(7) S1 0.0131(2) 0.0151(2) 0.0223(3) 0.00153(18) 0.00715(18) 0.00163(17) S2 0.0149(2) 0.0134(2) 0.0192(3) 0.00005(17) 0.00608(18) -0.00195(16) S3 0.0179(2) 0.0262(3) 0.0167(3) 0.00510(19) -0.00061(18) 0.00211(19) C1 0.0135(8) 0.0163(9) 0.0115(9) 0.0015(7) 0.0033(7) 0.0019(7) C2 0.0130(8) 0.0143(8) 0.0109(8) 0.0001(6) 0.0037(6) -0.0004(6) C3 0.0149(9) 0.0149(9) 0.0134(9) 0.0016(7) 0.0031(7) 0.0011(7) C4 0.0167(9) 0.0125(8) 0.0137(9) 0.0001(7) 0.0045(7) 0.0004(7) C5 0.0146(9) 0.0143(9) 0.0177(9) 0.0015(7) 0.0055(7) -0.0008(7) C6 0.0168(9) 0.0165(9) 0.0163(9) -0.0013(7) 0.0053(7) -0.0027(7) C7 0.0268(11) 0.0157(10) 0.0309(12) 0.0037(8) 0.0106(9) 0.0003(8) C8 0.0103(8) 0.0152(9) 0.0153(9) -0.0002(7) 0.0051(7) 0.0015(6) C9 0.0105(8) 0.0137(8) 0.0162(9) -0.0005(7) 0.0053(7) 0.0003(6) C10 0.0107(8) 0.0147(9) 0.0162(9) 0.0011(7) 0.0053(7) 0.0021(6) C11 0.0128(8) 0.0181(9) 0.0168(9) 0.0002(7) 0.0045(7) 0.0008(7) C12 0.0164(9) 0.0175(9) 0.0189(10) 0.0036(7) 0.0068(7) 0.0033(7) C13 0.0259(11) 0.0338(13) 0.0202(11) 0.0085(9) -0.0019(9) -0.0083(9) C14 0.0121(8) 0.0191(9) 0.0146(9) 0.0023(7) 0.0045(7) 0.0007(7) C15 0.0132(8) 0.0215(10) 0.0139(9) 0.0022(7) 0.0044(7) -0.0005(7) C16 0.0151(9) 0.0209(10) 0.0158(9) 0.0037(7) 0.0033(7) -0.0019(7) C17 0.0145(9) 0.0225(10) 0.0169(10) 0.0023(8) 0.0037(7) 0.0011(7) C18 0.0208(10) 0.0249(11) 0.0162(10) 0.0020(8) 0.0061(8) -0.0068(8) C19 0.0290(11) 0.0261(11) 0.0194(11) -0.0007(8) 0.0081(9) -0.0006(9) O4 0.048(3) 0.048(3) 0.042(3) -0.002(2) 0.007(2) 0.012(3) C20 0.025(3) 0.021(3) 0.019(3) 0.006(2) 0.014(2) 0.008(2) C21 0.043(4) 0.036(4) 0.043(4) 0.001(3) 0.023(3) 0.005(3) C22 0.036(4) 0.049(4) 0.027(4) 0.003(3) 0.012(3) 0.007(4) C31 0.028(3) 0.046(3) 0.031(3) 0.006(3) 0.010(2) 0.002(2) Cl1 0.0326(10) 0.0469(10) 0.0231(8) 0.0055(6) 0.0043(7) 0.0253(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 O1 C6 1.227(2) . ? O2 C12 1.228(2) . ? O3 C18 1.223(3) . ? S1 C5 1.706(2) . ? S1 C4 1.717(2) . ? S2 C11 1.708(2) . ? S2 C10 1.7217(19) . ? S3 C17 1.708(2) . ? S3 C16 1.727(2) . ? C1 C14 1.513(3) . ? C1 C8 1.518(3) . ? C1 C2 1.520(3) . ? C1 H1 1.0000 . ? C2 C5 1.366(3) . ? C2 C3 1.416(3) . ? C3 C4 1.373(3) . ? C3 H3 0.90(3) . ? C4 C6 1.466(3) . ? C5 H5 0.97(3) . ? C6 C7 1.496(3) . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C8 C11 1.374(3) . ? C8 C9 1.415(3) . ? C9 C10 1.376(3) . ? C9 H9 0.95(3) . ? C10 C12 1.457(3) . ? C11 H11 0.96(3) . ? C12 C13 1.498(3) . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C14 C17 1.366(3) . ? C14 C15 1.421(3) . ? C15 C16 1.373(3) . ? C15 H15 0.93(3) . ? C16 C18 1.468(3) . ? C17 H17 0.93(3) . ? C18 C19 1.496(3) . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? O4 C20 1.262(10) . ? C20 C22 1.531(9) . ? C20 C21 1.550(8) . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? C31 C31 1.481(12) 2_776 ? C31 Cl1 1.791(7) . ? C31 H31A 0.9900 . ? C31 H31B 0.9900 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C5 S1 C4 91.64(10) . . ? C11 S2 C10 91.58(10) . . ? C17 S3 C16 91.35(10) . . ? C14 C1 C8 113.77(15) . . ? C14 C1 C2 109.75(15) . . ? C8 C1 C2 111.37(16) . . ? C14 C1 H1 107.2 . . ? C8 C1 H1 107.2 . . ? C2 C1 H1 107.2 . . ? C5 C2 C3 111.65(17) . . ? C5 C2 C1 124.27(17) . . ? C3 C2 C1 124.03(17) . . ? C4 C3 C2 112.90(18) . . ? C4 C3 H3 122.7(16) . . ? C2 C3 H3 124.4(16) . . ? C3 C4 C6 130.10(19) . . ? C3 C4 S1 111.20(14) . . ? C6 C4 S1 118.68(15) . . ? C2 C5 S1 112.61(15) . . ? C2 C5 H5 127.1(15) . . ? S1 C5 H5 120.3(15) . . ? O1 C6 C4 119.96(19) . . ? O1 C6 C7 121.50(18) . . ? C4 C6 C7 118.52(18) . . ? C6 C7 H7A 109.5 . . ? C6 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C6 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C11 C8 C9 111.31(18) . . ? C11 C8 C1 126.39(18) . . ? C9 C8 C1 122.26(16) . . ? C10 C9 C8 113.31(17) . . ? C10 C9 H9 124.9(16) . . ? C8 C9 H9 121.7(16) . . ? C9 C10 C12 128.99(18) . . ? C9 C10 S2 111.05(15) . . ? C12 C10 S2 119.96(15) . . ? C8 C11 S2 112.75(16) . . ? C8 C11 H11 126.3(15) . . ? S2 C11 H11 120.9(15) . . ? O2 C12 C10 121.07(19) . . ? O2 C12 C13 120.4(2) . . ? C10 C12 C13 118.52(18) . . ? C12 C13 H13A 109.5 . . ? C12 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C12 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C17 C14 C15 111.60(18) . . ? C17 C14 C1 123.28(18) . . ? C15 C14 C1 125.07(18) . . ? C16 C15 C14 112.8(2) . . ? C16 C15 H15 123.2(16) . . ? C14 C15 H15 123.8(16) . . ? C15 C16 C18 130.2(2) . . ? C15 C16 S3 111.29(16) . . ? C18 C16 S3 118.46(16) . . ? C14 C17 S3 112.93(16) . . ? C14 C17 H17 126.9(19) . . ? S3 C17 H17 119.9(19) . . ? O3 C18 C16 119.8(2) . . ? O3 C18 C19 121.1(2) . . ? C16 C18 C19 119.10(19) . . ? C18 C19 H19A 109.5 . . ? C18 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C18 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? O4 C20 C22 118.0(8) . . ? O4 C20 C21 117.4(8) . . ? C22 C20 C21 124.4(10) . . ? C20 C21 H21A 109.5 . . ? C20 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C20 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C20 C22 H22A 109.5 . . ? C20 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C20 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C31 C31 Cl1 108.5(7) 2_776 . ? C31 C31 H31A 110.0 2_776 . ? Cl1 C31 H31A 110.0 . . ? C31 C31 H31B 110.0 2_776 . ? Cl1 C31 H31B 110.0 . . ? H31A C31 H31B 108.4 . . ? 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 C14 C1 C2 C5 82.4(2) . . . . ? C8 C1 C2 C5 -44.5(3) . . . . ? C14 C1 C2 C3 -94.8(2) . . . . ? C8 C1 C2 C3 138.31(19) . . . . ? C5 C2 C3 C4 -0.8(2) . . . . ? C1 C2 C3 C4 176.76(17) . . . . ? C2 C3 C4 C6 -177.7(2) . . . . ? C2 C3 C4 S1 0.5(2) . . . . ? C5 S1 C4 C3 -0.14(16) . . . . ? C5 S1 C4 C6 178.33(17) . . . . ? C3 C2 C5 S1 0.7(2) . . . . ? C1 C2 C5 S1 -176.87(15) . . . . ? C4 S1 C5 C2 -0.30(17) . . . . ? C3 C4 C6 O1 178.9(2) . . . . ? S1 C4 C6 O1 0.8(3) . . . . ? C3 C4 C6 C7 0.9(3) . . . . ? S1 C4 C6 C7 -177.27(16) . . . . ? C14 C1 C8 C11 12.7(3) . . . . ? C2 C1 C8 C11 137.38(19) . . . . ? C14 C1 C8 C9 -169.87(17) . . . . ? C2 C1 C8 C9 -45.2(2) . . . . ? C11 C8 C9 C10 -0.2(2) . . . . ? C1 C8 C9 C10 -177.93(17) . . . . ? C8 C9 C10 C12 -179.52(19) . . . . ? C8 C9 C10 S2 0.3(2) . . . . ? C11 S2 C10 C9 -0.32(15) . . . . ? C11 S2 C10 C12 179.54(16) . . . . ? C9 C8 C11 S2 -0.1(2) . . . . ? C1 C8 C11 S2 177.57(15) . . . . ? C10 S2 C11 C8 0.24(16) . . . . ? C9 C10 C12 O2 -178.4(2) . . . . ? S2 C10 C12 O2 1.8(3) . . . . ? C9 C10 C12 C13 1.9(3) . . . . ? S2 C10 C12 C13 -177.93(17) . . . . ? C8 C1 C14 C17 -125.6(2) . . . . ? C2 C1 C14 C17 108.9(2) . . . . ? C8 C1 C14 C15 57.1(2) . . . . ? C2 C1 C14 C15 -68.4(2) . . . . ? C17 C14 C15 C16 0.2(2) . . . . ? C1 C14 C15 C16 177.76(17) . . . . ? C14 C15 C16 C18 176.74(19) . . . . ? C14 C15 C16 S3 -0.2(2) . . . . ? C17 S3 C16 C15 0.14(16) . . . . ? C17 S3 C16 C18 -177.21(16) . . . . ? C15 C14 C17 S3 -0.1(2) . . . . ? C1 C14 C17 S3 -177.70(14) . . . . ? C16 S3 C17 C14 -0.03(16) . . . . ? C15 C16 C18 O3 -177.0(2) . . . . ? S3 C16 C18 O3 -0.2(3) . . . . ? C15 C16 C18 C19 4.0(3) . . . . ? S3 C16 C18 C19 -179.23(15) . . . . ? H1 C1 C14 C17 -7.2 . . . . ? H1 C1 C8 C11 -105.6 . . . . ? H1 C1 C2 C5 -161.4 . . . . ? _diffrn_measured_fraction_theta_max 0.945 _diffrn_reflns_theta_full 30.51 _diffrn_measured_fraction_theta_full 0.945 _refine_diff_density_max 0.578 _refine_diff_density_min -0.388 _refine_diff_density_rms 0.088 data_dce-ace-64-36 _database_code_depnum_ccdc_archive 'CCDC 677781' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '2(C19H16O3S3) 0.64(C2H4Cl2) 0.36(C3H6O1)' _chemical_formula_sum 'C40.36 H36.72 Cl1.28 O6.36 S6' _chemical_formula_weight 861.23 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.9656(6) _cell_length_b 10.9124(8) _cell_length_c 12.1583(9) _cell_angle_alpha 97.297(3) _cell_angle_beta 105.982(4) _cell_angle_gamma 96.641(4) _cell_volume 995.12(13) _cell_formula_units_Z 1 _cell_measurement_temperature 273(2) _cell_measurement_reflns_used 5785 _cell_measurement_theta_min 2.69 _cell_measurement_theta_max 34.85 _exptl_crystal_description block _exptl_crystal_colour 'pale yellow' _exptl_crystal_size_max 0.56 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_min 0.28 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.437 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 448 _exptl_absorpt_coefficient_mu 0.478 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7758 _exptl_absorpt_correction_T_max 0.8779 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 273(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 'Bruker Kappa APEXII CCD' _diffrn_measurement_method ' \f & \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 21863 _diffrn_reflns_av_R_equivalents 0.0296 _diffrn_reflns_av_sigmaI/netI 0.0412 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.69 _diffrn_reflns_theta_max 36.20 _reflns_number_total 9393 _reflns_number_gt 7471 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker, 2006)' _computing_cell_refinement 'SAINT (Bruker, 2006)' _computing_data_reduction 'SAINT (Bruker, 2006)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _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^)+(0.0683P)^2^+0.2812P] 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 9393 _refine_ls_number_parameters 317 _refine_ls_number_restraints 8 _refine_ls_R_factor_all 0.0582 _refine_ls_R_factor_gt 0.0444 _refine_ls_wR_factor_ref 0.1277 _refine_ls_wR_factor_gt 0.1184 _refine_ls_goodness_of_fit_ref 1.038 _refine_ls_restrained_S_all 1.038 _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 O1 O -0.14060(12) -0.06878(9) 0.14548(9) 0.02281(18) Uani 1 1 d . . . O2 O 0.56049(14) 0.47172(9) -0.23379(9) 0.02446(19) Uani 1 1 d . . . O3 O 0.94817(16) 0.42671(11) 0.67059(9) 0.0317(2) Uani 1 1 d . . . S1 S 0.08444(4) 0.16722(3) 0.15327(3) 0.01713(7) Uani 1 1 d . . . S2 S 0.75751(4) 0.45975(3) 0.01106(3) 0.01687(6) Uani 1 1 d . . . S3 S 0.91146(4) 0.20682(3) 0.49419(3) 0.02138(7) Uani 1 1 d . . . C1 C 0.59835(14) 0.17825(10) 0.16566(9) 0.01470(18) Uani 1 1 d . . . H1 H 0.6358 0.1016 0.1358 0.018 Uiso 1 1 calc R . . C2 C 0.40338(14) 0.14629(10) 0.15596(9) 0.01459(18) Uani 1 1 d . . . C3 C 0.31616(15) 0.02344(10) 0.14880(10) 0.01578(18) Uani 1 1 d . . . C4 C 0.14178(15) 0.01997(10) 0.14722(10) 0.01559(18) Uani 1 1 d . . . C5 C 0.29183(15) 0.23313(11) 0.15827(10) 0.01667(19) Uani 1 1 d . . . C6 C 0.00897(16) -0.08587(11) 0.14487(10) 0.0178(2) Uani 1 1 d . . . C7 C 0.06202(19) -0.21332(12) 0.14522(13) 0.0252(2) Uani 1 1 d . . . H7A H 0.1209 -0.2226 0.2233 0.038 Uiso 1 1 calc R . . H7B H 0.1406 -0.2230 0.0985 0.038 Uiso 1 1 calc R . . H7C H -0.0414 -0.2759 0.1141 0.038 Uiso 1 1 calc R . . C8 C 0.62859(14) 0.27479(10) 0.09066(9) 0.01420(17) Uani 1 1 d . . . C9 C 0.51991(14) 0.26729(10) -0.02523(9) 0.01475(18) Uani 1 1 d . . . C10 C 0.57364(14) 0.36088(10) -0.07947(10) 0.01496(18) Uani 1 1 d . . . C11 C 0.76246(15) 0.37542(11) 0.12092(10) 0.01702(19) Uani 1 1 d . . . C12 C 0.49524(16) 0.38388(11) -0.19753(10) 0.0180(2) Uani 1 1 d . . . C13 C 0.33086(19) 0.29884(15) -0.27243(12) 0.0288(3) Uani 1 1 d . . . H13A H 0.2294 0.3380 -0.2713 0.043 Uiso 1 1 calc R . . H13B H 0.3211 0.2214 -0.2434 0.043 Uiso 1 1 calc R . . H13C H 0.3370 0.2827 -0.3506 0.043 Uiso 1 1 calc R . . C14 C 0.70547(14) 0.21620(11) 0.29185(10) 0.01611(18) Uani 1 1 d . . . C15 C 0.69992(15) 0.32766(11) 0.36534(10) 0.01706(19) Uani 1 1 d . . . C16 C 0.80624(15) 0.33572(11) 0.47757(10) 0.0180(2) Uani 1 1 d . . . C17 C 0.81500(16) 0.14295(12) 0.35147(11) 0.0192(2) Uani 1 1 d . . . C18 C 0.84394(17) 0.43617(12) 0.57812(11) 0.0212(2) Uani 1 1 d . . . C19 C 0.75394(19) 0.54840(13) 0.56542(12) 0.0252(2) Uani 1 1 d . . . H19A H 0.6550 0.5398 0.5960 0.038 Uiso 1 1 calc R . . H19B H 0.7132 0.5555 0.4848 0.038 Uiso 1 1 calc R . . H19C H 0.8357 0.6220 0.6073 0.038 Uiso 1 1 calc R . . H3 H 0.367(2) -0.0400(17) 0.1461(15) 0.017(4) Uiso 1 1 d . . . H5 H 0.315(2) 0.3185(16) 0.1598(15) 0.017(4) Uiso 1 1 d . . . H9 H 0.422(2) 0.2049(17) -0.0579(16) 0.021(4) Uiso 1 1 d . . . H11 H 0.856(2) 0.4065(18) 0.1948(16) 0.024(4) Uiso 1 1 d . . . H15 H 0.637(3) 0.3877(18) 0.3406(16) 0.024(4) Uiso 1 1 d . . . H17 H 0.839(2) 0.0655(17) 0.3232(15) 0.019(4) Uiso 1 1 d . . . O4 O 0.5738(11) 0.1360(8) 0.6425(7) 0.0436(16) Uiso 0.18 1 d P A -1 C20 C 0.5106(15) 0.0649(9) 0.5513(10) 0.028(2) Uiso 0.18 1 d PD A -1 C21 C 0.3673(19) 0.0915(16) 0.4491(10) 0.048(3) Uiso 0.18 1 d PD A -1 H21A H 0.3293 0.1689 0.4708 0.072 Uiso 0.18 1 calc PR A -1 H21B H 0.2687 0.0248 0.4274 0.072 Uiso 0.18 1 calc PR A -1 H21C H 0.4137 0.0975 0.3846 0.072 Uiso 0.18 1 calc PR A -1 C22 C 0.5786(18) -0.0591(10) 0.5309(12) 0.041(2) Uiso 0.18 1 d PD A -1 H22A H 0.6627 -0.0703 0.6011 0.061 Uiso 0.18 1 calc PR A -1 H22B H 0.6345 -0.0580 0.4704 0.061 Uiso 0.18 1 calc PR A -1 H22C H 0.4813 -0.1268 0.5085 0.061 Uiso 0.18 1 calc PR A -1 C31 C 0.5555(19) -0.0023(16) 0.5587(9) 0.043(5) Uani 0.24 1 d PD . 2 H31A H 0.4803 -0.0280 0.6050 0.051 Uiso 0.24 1 calc PR . 2 H31B H 0.6189 0.0809 0.5945 0.051 Uiso 0.24 1 calc PR . 2 Cl1 Cl 0.7100(11) -0.1073(9) 0.5586(6) 0.0187(7) Uani 0.24 1 d PD B 2 C32 C 0.5186(16) -0.0555(9) 0.4673(9) 0.023(3) Uiso 0.15 1 d PD . 3 H32A H 0.5600 -0.0310 0.4042 0.028 Uiso 0.15 1 calc PR . 3 H32B H 0.4098 -0.1145 0.4337 0.028 Uiso 0.15 1 calc PR . 3 Cl2 Cl 0.6788(8) -0.1304(6) 0.5542(6) 0.0343(17) Uiso 0.15 1 d PD C 3 C33 C 0.5596(12) 0.0040(11) 0.5608(5) 0.016(2) Uani 0.25 1 d PD . 4 H33A H 0.4925 -0.0259 0.6103 0.019 Uiso 0.25 1 calc PR . 4 H33B H 0.6149 0.0898 0.5931 0.019 Uiso 0.25 1 calc PR . 4 Cl3 Cl 0.7225(12) -0.0919(9) 0.5505(8) 0.0302(18) Uani 0.25 1 d PD D 4 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0158(4) 0.0228(4) 0.0284(5) -0.0006(3) 0.0088(3) -0.0031(3) O2 0.0271(5) 0.0218(4) 0.0251(4) 0.0091(3) 0.0082(4) -0.0009(3) O3 0.0332(5) 0.0339(5) 0.0182(4) -0.0004(4) -0.0040(4) 0.0004(4) S1 0.01291(12) 0.01646(12) 0.02209(13) 0.00212(9) 0.00636(9) 0.00088(9) S2 0.01410(12) 0.01538(12) 0.01965(13) 0.00075(9) 0.00551(9) -0.00257(9) S3 0.01737(13) 0.02600(14) 0.01763(13) 0.00533(10) -0.00022(10) 0.00217(10) C1 0.0114(4) 0.0176(4) 0.0142(4) 0.0016(3) 0.0034(3) 0.0005(3) C2 0.0129(4) 0.0161(4) 0.0138(4) 0.0016(3) 0.0036(3) -0.0001(3) C3 0.0144(4) 0.0159(4) 0.0160(4) 0.0016(3) 0.0044(3) -0.0002(3) C4 0.0141(4) 0.0152(4) 0.0164(4) 0.0006(3) 0.0047(3) -0.0005(3) C5 0.0138(4) 0.0159(4) 0.0197(5) 0.0023(3) 0.0056(4) -0.0006(3) C6 0.0174(5) 0.0168(4) 0.0180(5) 0.0003(3) 0.0062(4) -0.0026(4) C7 0.0249(6) 0.0169(5) 0.0341(7) 0.0039(4) 0.0108(5) -0.0006(4) C8 0.0110(4) 0.0164(4) 0.0144(4) 0.0011(3) 0.0039(3) 0.0001(3) C9 0.0123(4) 0.0164(4) 0.0145(4) 0.0010(3) 0.0044(3) -0.0010(3) C10 0.0121(4) 0.0158(4) 0.0163(4) 0.0011(3) 0.0047(3) -0.0006(3) C11 0.0128(4) 0.0195(5) 0.0168(5) 0.0008(3) 0.0038(4) -0.0012(3) C12 0.0175(5) 0.0183(5) 0.0186(5) 0.0039(4) 0.0059(4) 0.0015(4) C13 0.0254(6) 0.0338(7) 0.0200(6) 0.0083(5) -0.0016(5) -0.0078(5) C14 0.0118(4) 0.0204(5) 0.0152(4) 0.0031(3) 0.0035(3) 0.0003(3) C15 0.0142(4) 0.0215(5) 0.0141(4) 0.0027(4) 0.0029(3) 0.0004(4) C16 0.0143(4) 0.0229(5) 0.0153(5) 0.0033(4) 0.0032(4) -0.0006(4) C17 0.0156(5) 0.0229(5) 0.0182(5) 0.0042(4) 0.0036(4) 0.0023(4) C18 0.0200(5) 0.0236(5) 0.0168(5) 0.0018(4) 0.0041(4) -0.0050(4) C19 0.0281(6) 0.0263(6) 0.0203(5) 0.0009(4) 0.0080(5) 0.0011(5) C31 0.040(8) 0.037(8) 0.055(9) 0.014(6) 0.022(6) -0.003(6) Cl1 0.0200(15) 0.0221(18) 0.0158(10) 0.0077(15) 0.0044(12) 0.0081(14) C33 0.012(3) 0.031(5) 0.005(2) 0.003(3) -0.001(2) 0.012(3) Cl3 0.0289(18) 0.035(3) 0.031(2) 0.0143(11) 0.0091(11) 0.0131(17) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C6 1.2289(15) . ? O2 C12 1.2255(15) . ? O3 C18 1.2244(16) . ? S1 C5 1.7056(12) . ? S1 C4 1.7187(12) . ? S2 C11 1.7100(13) . ? S2 C10 1.7222(11) . ? S3 C17 1.7094(13) . ? S3 C16 1.7243(13) . ? C1 C14 1.5132(15) . ? C1 C8 1.5185(16) . ? C1 C2 1.5201(15) . ? C1 H1 0.9800 . ? C2 C5 1.3749(16) . ? C2 C3 1.4174(15) . ? C3 C4 1.3799(16) . ? C3 H3 0.843(17) . ? C4 C6 1.4651(16) . ? C5 H5 0.925(18) . ? C6 C7 1.4998(18) . ? C7 H7A 0.9600 . ? C7 H7B 0.9600 . ? C7 H7C 0.9600 . ? C8 C11 1.3743(15) . ? C8 C9 1.4227(15) . ? C9 C10 1.3736(16) . ? C9 H9 0.931(19) . ? C10 C12 1.4654(16) . ? C11 H11 0.986(19) . ? C12 C13 1.5008(18) . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? C14 C17 1.3733(17) . ? C14 C15 1.4275(16) . ? C15 C16 1.3795(16) . ? C15 H15 0.901(19) . ? C16 C18 1.4722(17) . ? C17 H17 0.932(17) . ? C18 C19 1.493(2) . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? O4 C20 1.211(14) . ? C20 C21 1.523(9) . ? C20 C22 1.531(9) . ? C21 H21A 0.9600 . ? C21 H21B 0.9600 . ? C21 H21C 0.9600 . ? C22 H22A 0.9600 . ? C22 H22B 0.9600 . ? C22 H22C 0.9600 . ? C31 C31 1.467(17) 2_656 ? C31 Cl1 1.776(9) . ? C31 H31A 0.9700 . ? C31 H31B 0.9700 . ? C32 C32 1.469(15) 2_656 ? C32 Cl2 1.769(9) . ? C32 H32A 0.9700 . ? C32 H32B 0.9700 . ? C33 C33 1.507(9) 2_656 ? C33 Cl3 1.779(7) . ? C33 H33A 0.9700 . ? C33 H33B 0.9700 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C5 S1 C4 91.79(5) . . ? C11 S2 C10 91.58(5) . . ? C17 S3 C16 91.55(6) . . ? C14 C1 C8 113.54(9) . . ? C14 C1 C2 109.92(9) . . ? C8 C1 C2 111.39(9) . . ? C14 C1 H1 107.2 . . ? C8 C1 H1 107.2 . . ? C2 C1 H1 107.2 . . ? C5 C2 C3 111.61(10) . . ? C5 C2 C1 124.34(10) . . ? C3 C2 C1 123.98(10) . . ? C4 C3 C2 112.81(10) . . ? C4 C3 H3 124.4(12) . . ? C2 C3 H3 122.8(12) . . ? C3 C4 C6 130.17(11) . . ? C3 C4 S1 111.22(8) . . ? C6 C4 S1 118.58(9) . . ? C2 C5 S1 112.56(8) . . ? C2 C5 H5 128.7(11) . . ? S1 C5 H5 118.7(11) . . ? O1 C6 C4 120.10(11) . . ? O1 C6 C7 121.46(11) . . ? C4 C6 C7 118.41(11) . . ? C6 C7 H7A 109.5 . . ? C6 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C6 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C11 C8 C9 111.29(10) . . ? C11 C8 C1 126.42(10) . . ? C9 C8 C1 122.25(9) . . ? C10 C9 C8 113.08(10) . . ? C10 C9 H9 125.4(11) . . ? C8 C9 H9 121.5(11) . . ? C9 C10 C12 128.75(10) . . ? C9 C10 S2 111.33(8) . . ? C12 C10 S2 119.92(8) . . ? C8 C11 S2 112.73(9) . . ? C8 C11 H11 130.5(11) . . ? S2 C11 H11 116.8(11) . . ? O2 C12 C10 120.87(11) . . ? O2 C12 C13 120.64(12) . . ? C10 C12 C13 118.48(11) . . ? C12 C13 H13A 109.5 . . ? C12 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C12 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C17 C14 C15 111.46(10) . . ? C17 C14 C1 123.32(10) . . ? C15 C14 C1 125.15(10) . . ? C16 C15 C14 112.62(11) . . ? C16 C15 H15 123.5(12) . . ? C14 C15 H15 123.8(12) . . ? C15 C16 C18 130.06(12) . . ? C15 C16 S3 111.47(9) . . ? C18 C16 S3 118.44(9) . . ? C14 C17 S3 112.90(9) . . ? C14 C17 H17 127.8(11) . . ? S3 C17 H17 119.3(11) . . ? O3 C18 C16 119.81(13) . . ? O3 C18 C19 120.99(12) . . ? C16 C18 C19 119.20(11) . . ? C18 C19 H19A 109.5 . . ? C18 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C18 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? O4 C20 C21 124.3(10) . . ? O4 C20 C22 120.3(10) . . ? C21 C20 C22 115.3(13) . . ? C20 C21 H21A 109.5 . . ? C20 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C20 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C20 C22 H22A 109.5 . . ? C20 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C20 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C31 C31 Cl1 112.4(12) 2_656 . ? C31 C31 H31A 109.1 2_656 . ? Cl1 C31 H31A 109.1 . . ? C31 C31 H31B 109.1 2_656 . ? Cl1 C31 H31B 109.1 . . ? H31A C31 H31B 107.9 . . ? C32 C32 Cl2 112.8(11) 2_656 . ? C32 C32 H32A 109.0 2_656 . ? Cl2 C32 H32A 109.0 . . ? C32 C32 H32B 109.0 2_656 . ? Cl2 C32 H32B 109.0 . . ? H32A C32 H32B 107.8 . . ? C33 C33 Cl3 106.4(7) 2_656 . ? C33 C33 H33A 110.4 2_656 . ? Cl3 C33 H33A 110.4 . . ? C33 C33 H33B 110.4 2_656 . ? Cl3 C33 H33B 110.4 . . ? H33A C33 H33B 108.6 . . ? 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 C14 C1 C2 C5 82.57(13) . . . . ? C8 C1 C2 C5 -44.17(14) . . . . ? C14 C1 C2 C3 -94.38(12) . . . . ? C8 C1 C2 C3 138.88(11) . . . . ? C5 C2 C3 C4 -0.71(14) . . . . ? C1 C2 C3 C4 176.58(10) . . . . ? C2 C3 C4 C6 -177.44(11) . . . . ? C2 C3 C4 S1 0.51(13) . . . . ? C5 S1 C4 C3 -0.15(9) . . . . ? C5 S1 C4 C6 178.07(10) . . . . ? C3 C2 C5 S1 0.59(13) . . . . ? C1 C2 C5 S1 -176.69(9) . . . . ? C4 S1 C5 C2 -0.26(9) . . . . ? C3 C4 C6 O1 178.91(12) . . . . ? S1 C4 C6 O1 1.09(16) . . . . ? C3 C4 C6 C7 0.64(19) . . . . ? S1 C4 C6 C7 -177.18(9) . . . . ? C14 C1 C8 C11 13.37(16) . . . . ? C2 C1 C8 C11 138.10(11) . . . . ? C14 C1 C8 C9 -169.16(10) . . . . ? C2 C1 C8 C9 -44.42(14) . . . . ? C11 C8 C9 C10 0.23(14) . . . . ? C1 C8 C9 C10 -177.59(10) . . . . ? C8 C9 C10 C12 -179.78(11) . . . . ? C8 C9 C10 S2 -0.28(12) . . . . ? C11 S2 C10 C9 0.20(9) . . . . ? C11 S2 C10 C12 179.75(10) . . . . ? C9 C8 C11 S2 -0.07(13) . . . . ? C1 C8 C11 S2 177.63(9) . . . . ? C10 S2 C11 C8 -0.07(9) . . . . ? C9 C10 C12 O2 -179.32(12) . . . . ? S2 C10 C12 O2 1.21(16) . . . . ? C9 C10 C12 C13 1.86(19) . . . . ? S2 C10 C12 C13 -177.61(10) . . . . ? C8 C1 C14 C17 -125.96(12) . . . . ? C2 C1 C14 C17 108.51(12) . . . . ? C8 C1 C14 C15 57.34(14) . . . . ? C2 C1 C14 C15 -68.18(14) . . . . ? C17 C14 C15 C16 0.54(15) . . . . ? C1 C14 C15 C16 177.57(10) . . . . ? C14 C15 C16 C18 177.19(12) . . . . ? C14 C15 C16 S3 -0.61(13) . . . . ? C17 S3 C16 C15 0.41(10) . . . . ? C17 S3 C16 C18 -177.68(10) . . . . ? C15 C14 C17 S3 -0.22(13) . . . . ? C1 C14 C17 S3 -177.32(9) . . . . ? C16 S3 C17 C14 -0.10(10) . . . . ? C15 C16 C18 O3 -177.58(13) . . . . ? S3 C16 C18 O3 0.09(17) . . . . ? C15 C16 C18 C19 2.4(2) . . . . ? S3 C16 C18 C19 -179.93(10) . . . . ? H1 C1 C2 C5 -161.2 . . . . ? H1 C1 C8 C11 -104.9 . . . . ? H1 C1 C14 C17 -7.7 . . . . ? _diffrn_measured_fraction_theta_max 0.981 _diffrn_reflns_theta_full 36.20 _diffrn_measured_fraction_theta_full 0.981 _refine_diff_density_max 0.879 _refine_diff_density_min -0.458 _refine_diff_density_rms 0.091 data_dce-ace-76-24 _database_code_depnum_ccdc_archive 'CCDC 677782' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '2(C19H16O3S3) 0.76(C2H4Cl2) 0.24(C3H6O1)' _chemical_formula_sum 'C40.24 H36.48 Cl1.52 O6.24 S6' _chemical_formula_weight 866.14 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.9555(3) _cell_length_b 10.9385(5) _cell_length_c 12.1457(5) _cell_angle_alpha 97.452(2) _cell_angle_beta 105.862(2) _cell_angle_gamma 96.676(2) _cell_volume 995.27(7) _cell_formula_units_Z 1 _cell_measurement_temperature 100(1) _cell_measurement_reflns_used 6733 _cell_measurement_theta_min 2.37 _cell_measurement_theta_max 42.89 _exptl_crystal_description block _exptl_crystal_colour 'pale yellow' _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.445 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 450 _exptl_absorpt_coefficient_mu 0.493 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8463 _exptl_absorpt_correction_T_max 0.9432 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 'Bruker Kappa APEXII CCD' _diffrn_measurement_method ' \f & \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 43763 _diffrn_reflns_av_R_equivalents 0.0246 _diffrn_reflns_av_sigmaI/netI 0.0298 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.81 _diffrn_reflns_theta_max 43.07 _reflns_number_total 14668 _reflns_number_gt 11140 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker, 2006)' _computing_cell_refinement 'SAINT (Bruker, 2006)' _computing_data_reduction 'SAINT (Bruker, 2006)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _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^)+(0.0485P)^2^+0.2857P] 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 14668 _refine_ls_number_parameters 303 _refine_ls_number_restraints 7 _refine_ls_R_factor_all 0.0570 _refine_ls_R_factor_gt 0.0368 _refine_ls_wR_factor_ref 0.1095 _refine_ls_wR_factor_gt 0.0929 _refine_ls_goodness_of_fit_ref 1.062 _refine_ls_restrained_S_all 1.062 _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 O1 O -0.64106(8) 0.43145(6) 0.14541(6) 0.02071(11) Uani 1 1 d . . . O2 O 0.06117(9) 0.97203(6) -0.23302(6) 0.02241(11) Uani 1 1 d . . . O3 O 0.44607(11) 0.92717(8) 0.67081(6) 0.02830(14) Uani 1 1 d . . . S1 S -0.41635(2) 0.666988(17) 0.152432(17) 0.01517(4) Uani 1 1 d . . . S2 S 0.25836(2) 0.959893(17) 0.011318(17) 0.01504(4) Uani 1 1 d . . . S3 S 0.41062(3) 0.70801(2) 0.494351(18) 0.01888(4) Uani 1 1 d . . . C1 C 0.09875(9) 0.67897(7) 0.16545(6) 0.01333(10) Uani 1 1 d . . . H1 H 0.1373 0.6010 0.1348 0.016 Uiso 1 1 calc R . . C2 C -0.09652(8) 0.64677(6) 0.15577(6) 0.01264(9) Uani 1 1 d . . . C3 C -0.18374(9) 0.52390(7) 0.14866(6) 0.01388(10) Uani 1 1 d . . . C4 C -0.35855(9) 0.52010(6) 0.14681(6) 0.01387(10) Uani 1 1 d . . . C5 C -0.20881(9) 0.73304(7) 0.15771(7) 0.01480(10) Uani 1 1 d . . . C6 C -0.49130(10) 0.41446(7) 0.14460(7) 0.01599(11) Uani 1 1 d . . . C7 C -0.43783(12) 0.28732(8) 0.14576(9) 0.02316(15) Uani 1 1 d . . . H7A H -0.3795 0.2782 0.2258 0.035 Uiso 1 1 calc R . . H7B H -0.3559 0.2775 0.0990 0.035 Uiso 1 1 calc R . . H7C H -0.5432 0.2233 0.1132 0.035 Uiso 1 1 calc R . . C8 C 0.12899(8) 0.77525(6) 0.09077(6) 0.01270(10) Uani 1 1 d . . . C9 C 0.02009(9) 0.76770(7) -0.02503(6) 0.01300(10) Uani 1 1 d . . . C10 C 0.07381(9) 0.86122(6) -0.07918(6) 0.01333(10) Uani 1 1 d . . . C11 C 0.26320(9) 0.87563(7) 0.12108(6) 0.01510(11) Uani 1 1 d . . . C12 C -0.00476(10) 0.88441(7) -0.19695(7) 0.01591(11) Uani 1 1 d . . . C13 C -0.16933(13) 0.79948(10) -0.27207(8) 0.02556(17) Uani 1 1 d . . . H13A H -0.2730 0.8393 -0.2706 0.038 Uiso 1 1 calc R . . H13B H -0.1794 0.7205 -0.2427 0.038 Uiso 1 1 calc R . . H13C H -0.1630 0.7832 -0.3520 0.038 Uiso 1 1 calc R . . C14 C 0.20526(9) 0.71698(7) 0.29194(6) 0.01390(10) Uani 1 1 d . . . C15 C 0.19965(9) 0.82833(7) 0.36539(6) 0.01510(11) Uani 1 1 d . . . C16 C 0.30522(9) 0.83669(7) 0.47766(6) 0.01575(11) Uani 1 1 d . . . C17 C 0.31506(10) 0.64414(8) 0.35151(7) 0.01684(11) Uani 1 1 d . . . C18 C 0.34248(10) 0.93702(8) 0.57825(7) 0.01837(12) Uani 1 1 d . . . C19 C 0.25328(13) 1.04957(9) 0.56556(8) 0.02275(14) Uani 1 1 d . . . H19A H 0.1558 1.0434 0.6004 0.034 Uiso 1 1 calc R . . H19B H 0.2066 1.0542 0.4830 0.034 Uiso 1 1 calc R . . H19C H 0.3389 1.1249 0.6049 0.034 Uiso 1 1 calc R . . H3 H -0.1339(19) 0.4573(13) 0.1467(12) 0.018(3) Uiso 1 1 d . . . H15 H 0.133(2) 0.8919(14) 0.3400(13) 0.026(4) Uiso 1 1 d . . . H11 H 0.355(2) 0.9033(15) 0.1933(14) 0.026(4) Uiso 1 1 d . . . H17 H 0.338(2) 0.5683(14) 0.3230(13) 0.025(3) Uiso 1 1 d . . . H9 H -0.0799(19) 0.7053(13) -0.0583(13) 0.019(3) Uiso 1 1 d . . . H5 H -0.183(2) 0.8217(14) 0.1604(13) 0.022(3) Uiso 1 1 d . . . O4 O 1.0714(12) 0.6337(8) 0.6433(7) 0.0411(17) Uiso 0.12 1 d PD A -1 C20 C 1.0106(14) 0.5651(9) 0.5517(8) 0.028(2) Uiso 0.12 1 d PD A -1 C21 C 0.8706(18) 0.5917(16) 0.4485(11) 0.045(3) Uiso 0.12 1 d PD A -1 H21A H 0.8239 0.6667 0.4720 0.067 Uiso 0.12 1 calc PR A -1 H21B H 0.7741 0.5205 0.4208 0.067 Uiso 0.12 1 calc PR A -1 H21C H 0.9233 0.6051 0.3861 0.067 Uiso 0.12 1 calc PR A -1 C22 C 1.0815(17) 0.4422(10) 0.5317(12) 0.040(2) Uiso 0.12 1 d PD A -1 H22A H 1.1490 0.4236 0.6064 0.060 Uiso 0.12 1 calc PR A -1 H22B H 1.1586 0.4500 0.4815 0.060 Uiso 0.12 1 calc PR A -1 H22C H 0.9822 0.3744 0.4943 0.060 Uiso 0.12 1 calc PR A -1 Cl1 Cl 0.7840(2) 0.6001(2) 0.4456(2) 0.0301(2) Uani 0.57 1 d PD B 2 C31 C 0.9420(2) 0.49845(17) 0.43948(13) 0.0222(2) Uani 0.57 1 d PD . 2 H31A H 0.8806 0.4123 0.4053 0.027 Uiso 0.57 1 calc PR . 2 H31B H 1.0148 0.5259 0.3902 0.027 Uiso 0.57 1 calc PR . 2 Cl2 Cl 0.8119(8) 0.6217(7) 0.4441(7) 0.0356(10) Uani 0.19 1 d PD C 3 C32 C 0.9801(9) 0.5557(5) 0.5337(6) 0.0241(11) Uiso 0.19 1 d PD . 3 H32A H 1.0886 0.6187 0.5656 0.029 Uiso 0.19 1 calc PR . 3 H32B H 0.9416 0.5308 0.5996 0.029 Uiso 0.19 1 calc PR . 3 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0150(2) 0.0189(2) 0.0266(3) -0.0005(2) 0.0079(2) -0.00317(18) O2 0.0253(3) 0.0191(3) 0.0229(3) 0.0090(2) 0.0066(2) -0.0010(2) O3 0.0302(3) 0.0293(3) 0.0161(2) -0.0002(2) -0.0050(2) 0.0010(3) S1 0.01186(6) 0.01355(7) 0.01975(8) 0.00166(5) 0.00504(5) 0.00092(5) S2 0.01304(6) 0.01246(7) 0.01775(7) 0.00046(5) 0.00426(5) -0.00252(5) S3 0.01566(7) 0.02190(9) 0.01597(7) 0.00465(6) -0.00090(6) 0.00240(6) C1 0.0111(2) 0.0146(2) 0.0131(2) 0.00130(19) 0.00263(18) 0.00048(18) C2 0.0112(2) 0.0127(2) 0.0127(2) 0.00112(18) 0.00264(17) -0.00037(17) C3 0.0129(2) 0.0131(2) 0.0146(2) 0.00147(19) 0.00335(19) 0.00025(18) C4 0.0128(2) 0.0118(2) 0.0156(3) 0.00072(19) 0.00376(19) -0.00061(18) C5 0.0128(2) 0.0127(2) 0.0182(3) 0.0020(2) 0.0044(2) 0.00020(18) C6 0.0153(2) 0.0136(3) 0.0175(3) 0.0002(2) 0.0052(2) -0.0023(2) C7 0.0246(3) 0.0131(3) 0.0317(4) 0.0039(3) 0.0096(3) -0.0006(2) C8 0.0105(2) 0.0136(2) 0.0127(2) 0.00075(18) 0.00283(17) -0.00015(17) C9 0.0111(2) 0.0133(2) 0.0130(2) 0.00130(18) 0.00278(18) -0.00112(18) C10 0.0120(2) 0.0127(2) 0.0144(2) 0.00125(19) 0.00377(18) -0.00024(18) C11 0.0122(2) 0.0157(3) 0.0145(2) 0.0000(2) 0.00218(19) -0.00189(19) C12 0.0159(2) 0.0156(3) 0.0162(3) 0.0037(2) 0.0047(2) 0.0013(2) C13 0.0235(3) 0.0291(4) 0.0175(3) 0.0074(3) -0.0020(3) -0.0071(3) C14 0.0107(2) 0.0161(3) 0.0134(2) 0.0022(2) 0.00196(18) 0.00037(18) C15 0.0133(2) 0.0177(3) 0.0128(2) 0.0021(2) 0.00216(19) 0.0009(2) C16 0.0139(2) 0.0180(3) 0.0131(2) 0.0023(2) 0.00165(19) -0.0005(2) C17 0.0139(2) 0.0189(3) 0.0165(3) 0.0035(2) 0.0021(2) 0.0029(2) C18 0.0178(3) 0.0200(3) 0.0139(3) 0.0012(2) 0.0026(2) -0.0035(2) C19 0.0268(4) 0.0211(3) 0.0190(3) 0.0007(3) 0.0069(3) 0.0011(3) Cl1 0.0281(4) 0.0380(6) 0.0250(3) 0.0068(3) 0.0032(3) 0.0170(4) C31 0.0198(5) 0.0304(7) 0.0168(5) 0.0051(5) 0.0044(4) 0.0073(5) Cl2 0.044(2) 0.044(2) 0.0224(8) 0.0056(14) 0.0082(14) 0.0243(18) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C6 1.2294(10) . ? O2 C12 1.2260(10) . ? O3 C18 1.2248(10) . ? S1 C5 1.7044(7) . ? S1 C4 1.7199(7) . ? S2 C11 1.7109(8) . ? S2 C10 1.7235(7) . ? S3 C17 1.7079(8) . ? S3 C16 1.7266(8) . ? C1 C14 1.5139(9) . ? C1 C8 1.5159(10) . ? C1 C2 1.5210(9) . ? C1 H1 1.0000 . ? C2 C5 1.3751(10) . ? C2 C3 1.4197(10) . ? C3 C4 1.3804(10) . ? C3 H3 0.870(14) . ? C4 C6 1.4643(10) . ? C5 H5 0.962(15) . ? C6 C7 1.5015(12) . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C8 C11 1.3744(10) . ? C8 C9 1.4222(10) . ? C9 C10 1.3741(10) . ? C9 H9 0.942(14) . ? C10 C12 1.4641(10) . ? C11 H11 0.961(16) . ? C12 C13 1.5013(11) . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C14 C17 1.3738(10) . ? C14 C15 1.4261(11) . ? C15 C16 1.3773(10) . ? C15 H15 0.957(15) . ? C16 C18 1.4709(11) . ? C17 H17 0.916(15) . ? C18 C19 1.4952(13) . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? O4 C20 1.200(8) . ? C20 C21 1.517(9) . ? C20 C22 1.533(9) . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? Cl1 C31 1.783(3) . ? C31 C31 1.500(3) 2_766 ? C31 H31A 0.9900 . ? C31 H31B 0.9900 . ? Cl2 C32 1.769(7) . ? C32 C32 1.492(10) 2_766 ? C32 H32A 0.9900 . ? C32 H32B 0.9900 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C5 S1 C4 91.83(3) . . ? C11 S2 C10 91.51(3) . . ? C17 S3 C16 91.54(4) . . ? C14 C1 C8 113.60(6) . . ? C14 C1 C2 109.73(6) . . ? C8 C1 C2 111.39(6) . . ? C14 C1 H1 107.3 . . ? C8 C1 H1 107.3 . . ? C2 C1 H1 107.3 . . ? C5 C2 C3 111.52(6) . . ? C5 C2 C1 124.45(6) . . ? C3 C2 C1 123.98(6) . . ? C4 C3 C2 112.84(6) . . ? C4 C3 H3 122.5(9) . . ? C2 C3 H3 124.6(9) . . ? C3 C4 C6 130.22(7) . . ? C3 C4 S1 111.16(5) . . ? C6 C4 S1 118.59(5) . . ? C2 C5 S1 112.65(5) . . ? C2 C5 H5 127.9(9) . . ? S1 C5 H5 119.5(9) . . ? O1 C6 C4 120.08(7) . . ? O1 C6 C7 121.41(7) . . ? C4 C6 C7 118.47(7) . . ? C6 C7 H7A 109.5 . . ? C6 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C6 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C11 C8 C9 111.33(6) . . ? C11 C8 C1 126.43(6) . . ? C9 C8 C1 122.20(6) . . ? C10 C9 C8 113.06(6) . . ? C10 C9 H9 125.1(9) . . ? C8 C9 H9 121.8(9) . . ? C9 C10 C12 128.82(6) . . ? C9 C10 S2 111.35(5) . . ? C12 C10 S2 119.83(5) . . ? C8 C11 S2 112.75(5) . . ? C8 C11 H11 129.3(9) . . ? S2 C11 H11 118.0(9) . . ? O2 C12 C10 120.78(7) . . ? O2 C12 C13 120.72(7) . . ? C10 C12 C13 118.50(7) . . ? C12 C13 H13A 109.5 . . ? C12 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C12 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C17 C14 C15 111.50(6) . . ? C17 C14 C1 123.31(7) . . ? C15 C14 C1 125.14(6) . . ? C16 C15 C14 112.69(7) . . ? C16 C15 H15 123.0(9) . . ? C14 C15 H15 124.3(9) . . ? C15 C16 C18 130.12(7) . . ? C15 C16 S3 111.41(6) . . ? C18 C16 S3 118.43(6) . . ? C14 C17 S3 112.86(6) . . ? C14 C17 H17 127.2(10) . . ? S3 C17 H17 119.9(10) . . ? O3 C18 C16 119.56(8) . . ? O3 C18 C19 121.12(8) . . ? C16 C18 C19 119.31(7) . . ? C18 C19 H19A 109.5 . . ? C18 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C18 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? O4 C20 C21 125.2(10) . . ? O4 C20 C22 119.4(10) . . ? C21 C20 C22 115.4(12) . . ? C20 C21 H21A 109.5 . . ? C20 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C20 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C20 C22 H22A 109.5 . . ? C20 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C20 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C31 C31 Cl1 108.59(17) 2_766 . ? C31 C31 H31A 110.0 2_766 . ? Cl1 C31 H31A 110.0 . . ? C31 C31 H31B 110.0 2_766 . ? Cl1 C31 H31B 110.0 . . ? H31A C31 H31B 108.4 . . ? C32 C32 Cl2 110.6(7) 2_766 . ? C32 C32 H32A 109.5 2_766 . ? Cl2 C32 H32A 109.5 . . ? C32 C32 H32B 109.5 2_766 . ? Cl2 C32 H32B 109.5 . . ? H32A C32 H32B 108.1 . . ? 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 C14 C1 C2 C5 82.90(9) . . . . ? C8 C1 C2 C5 -43.78(9) . . . . ? C14 C1 C2 C3 -94.25(8) . . . . ? C8 C1 C2 C3 139.07(7) . . . . ? C5 C2 C3 C4 -0.74(9) . . . . ? C1 C2 C3 C4 176.73(6) . . . . ? C2 C3 C4 C6 -177.34(7) . . . . ? C2 C3 C4 S1 0.56(8) . . . . ? C5 S1 C4 C3 -0.19(6) . . . . ? C5 S1 C4 C6 177.98(6) . . . . ? C3 C2 C5 S1 0.59(8) . . . . ? C1 C2 C5 S1 -176.87(5) . . . . ? C4 S1 C5 C2 -0.24(6) . . . . ? C3 C4 C6 O1 178.60(8) . . . . ? S1 C4 C6 O1 0.83(10) . . . . ? C3 C4 C6 C7 0.80(13) . . . . ? S1 C4 C6 C7 -176.96(6) . . . . ? C14 C1 C8 C11 13.80(10) . . . . ? C2 C1 C8 C11 138.33(7) . . . . ? C14 C1 C8 C9 -168.84(6) . . . . ? C2 C1 C8 C9 -44.31(9) . . . . ? C11 C8 C9 C10 0.11(9) . . . . ? C1 C8 C9 C10 -177.61(6) . . . . ? C8 C9 C10 C12 -179.66(7) . . . . ? C8 C9 C10 S2 -0.13(8) . . . . ? C11 S2 C10 C9 0.09(6) . . . . ? C11 S2 C10 C12 179.66(6) . . . . ? C9 C8 C11 S2 -0.04(8) . . . . ? C1 C8 C11 S2 177.56(6) . . . . ? C10 S2 C11 C8 -0.03(6) . . . . ? C9 C10 C12 O2 -179.10(8) . . . . ? S2 C10 C12 O2 1.41(11) . . . . ? C9 C10 C12 C13 1.70(12) . . . . ? S2 C10 C12 C13 -177.79(7) . . . . ? C8 C1 C14 C17 -125.92(8) . . . . ? C2 C1 C14 C17 108.66(8) . . . . ? C8 C1 C14 C15 56.92(9) . . . . ? C2 C1 C14 C15 -68.50(9) . . . . ? C17 C14 C15 C16 0.22(9) . . . . ? C1 C14 C15 C16 177.66(7) . . . . ? C14 C15 C16 C18 177.29(7) . . . . ? C14 C15 C16 S3 -0.45(8) . . . . ? C17 S3 C16 C15 0.44(6) . . . . ? C17 S3 C16 C18 -177.59(6) . . . . ? C15 C14 C17 S3 0.12(8) . . . . ? C1 C14 C17 S3 -177.38(5) . . . . ? C16 S3 C17 C14 -0.32(6) . . . . ? C15 C16 C18 O3 -177.76(9) . . . . ? S3 C16 C18 O3 -0.15(11) . . . . ? C15 C16 C18 C19 2.11(13) . . . . ? S3 C16 C18 C19 179.71(6) . . . . ? H1 C1 C14 C17 -7.6 . . . . ? H1 C1 C8 C11 -104.6 . . . . ? H1 C1 C2 C5 -160.9 . . . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 43.07 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.730 _refine_diff_density_min -0.788 _refine_diff_density_rms 0.085 data_dce-ace-100-0 _database_code_depnum_ccdc_archive 'CCDC 677783' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '2(C19H16O3S3) 1.0(C2H4Cl2)' _chemical_formula_sum 'C40 H36 Cl2 O6 S6' _chemical_formula_weight 875.95 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.9495(7) _cell_length_b 10.9743(10) _cell_length_c 12.1800(12) _cell_angle_alpha 97.623(5) _cell_angle_beta 105.816(4) _cell_angle_gamma 96.665(4) _cell_volume 1000.33(16) _cell_formula_units_Z 1 _cell_measurement_temperature 100(1) _cell_measurement_reflns_used 9870 _cell_measurement_theta_min 2.70 _cell_measurement_theta_max 38.99 _exptl_crystal_description block _exptl_crystal_colour 'pale yellow' _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.454 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 454 _exptl_absorpt_coefficient_mu 0.522 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8383 _exptl_absorpt_correction_T_max 0.9027 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(1) _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 'Bruker Kappa APEXII CCD' _diffrn_measurement_method ' \f & \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 35685 _diffrn_reflns_av_R_equivalents 0.0238 _diffrn_reflns_av_sigmaI/netI 0.0297 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.70 _diffrn_reflns_theta_max 38.89 _reflns_number_total 11389 _reflns_number_gt 9237 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker, 2006)' _computing_cell_refinement 'SAINT (Bruker, 2006)' _computing_data_reduction 'SAINT (Bruker, 2006)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _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^)+(0.0479P)^2^+0.1954P] 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 11389 _refine_ls_number_parameters 290 _refine_ls_number_restraints 16 _refine_ls_R_factor_all 0.0456 _refine_ls_R_factor_gt 0.0335 _refine_ls_wR_factor_ref 0.0949 _refine_ls_wR_factor_gt 0.0883 _refine_ls_goodness_of_fit_ref 1.030 _refine_ls_restrained_S_all 1.031 _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 O1 O 0.05597(10) 0.07197(7) -0.17124(6) 0.02711(15) Uani 1 1 d . . . O2 O 0.43764(9) 0.02765(6) 0.73186(6) 0.02195(12) Uani 1 1 d . . . O3 O 1.14177(8) 0.56825(6) 0.35473(6) 0.02043(12) Uani 1 1 d . . . S1 S 0.08977(3) 0.29014(2) 0.005273(18) 0.01797(4) Uani 1 1 d . . . S2 S 0.24044(2) 0.040025(18) 0.487921(18) 0.01469(4) Uani 1 1 d . . . S3 S 0.91777(2) 0.333229(18) 0.348945(18) 0.01465(4) Uani 1 1 d . . . C1 C 0.40104(9) 0.32015(7) 0.33434(6) 0.01304(11) Uani 1 1 d . . . H1 H 0.3629 0.3963 0.3641 0.016 Uiso 1 1 calc R . . C2 C 0.29462(9) 0.28168(7) 0.20779(7) 0.01364(12) Uani 1 1 d . . . C3 C 0.30099(10) 0.17056(7) 0.13442(7) 0.01458(12) Uani 1 1 d . . . C4 C 0.19574(10) 0.16185(8) 0.02214(7) 0.01522(12) Uani 1 1 d . . . C5 C 0.18477(10) 0.35416(8) 0.14810(7) 0.01633(13) Uani 1 1 d . . . C6 C 0.15877(11) 0.06179(8) -0.07844(7) 0.01741(13) Uani 1 1 d . . . C7 C 0.24759(13) -0.05118(9) -0.06581(8) 0.02167(15) Uani 1 1 d . . . H7A H 0.1644 -0.1243 -0.1068 0.033 Uiso 1 1 calc R . . H7B H 0.2892 -0.0573 0.0147 0.033 Uiso 1 1 calc R . . H7C H 0.3460 -0.0441 -0.0972 0.033 Uiso 1 1 calc R . . C8 C 0.37053(9) 0.22416(7) 0.40908(6) 0.01258(11) Uani 1 1 d . . . C9 C 0.47957(9) 0.23188(7) 0.52459(6) 0.01267(11) Uani 1 1 d . . . C10 C 0.42540(9) 0.13837(7) 0.57851(7) 0.01312(11) Uani 1 1 d . . . C11 C 0.23590(10) 0.12409(7) 0.37840(7) 0.01493(12) Uani 1 1 d . . . C12 C 0.50397(10) 0.11521(7) 0.69620(7) 0.01542(12) Uani 1 1 d . . . C13 C 0.66842(13) 0.20016(9) 0.77187(8) 0.02377(17) Uani 1 1 d . . . H13A H 0.6611 0.2164 0.8497 0.036 Uiso 1 1 calc R . . H13B H 0.6790 0.2772 0.7431 0.036 Uiso 1 1 calc R . . H13C H 0.7702 0.1612 0.7711 0.036 Uiso 1 1 calc R . . C14 C 0.59674(9) 0.35267(7) 0.34448(6) 0.01245(11) Uani 1 1 d . . . C15 C 0.68346(10) 0.47538(7) 0.35100(7) 0.01360(12) Uani 1 1 d . . . C16 C 0.85897(10) 0.47965(7) 0.35353(7) 0.01357(12) Uani 1 1 d . . . C17 C 0.70992(10) 0.26698(7) 0.34325(7) 0.01448(12) Uani 1 1 d . . . C18 C 0.99150(10) 0.58497(7) 0.35493(7) 0.01584(13) Uani 1 1 d . . . C19 C 0.93747(13) 0.71168(8) 0.35274(9) 0.02276(16) Uani 1 1 d . . . H19A H 1.0403 0.7745 0.3856 0.034 Uiso 1 1 calc R . . H19B H 0.8553 0.7212 0.3970 0.034 Uiso 1 1 calc R . . H19C H 0.8824 0.7202 0.2742 0.034 Uiso 1 1 calc R . . H3 H 0.3653(19) 0.1108(13) 0.1582(12) 0.025(3) Uiso 1 1 d . . . H5 H 0.1619(18) 0.4320(13) 0.1780(12) 0.021(3) Uiso 1 1 d . . . H9 H 0.5772(17) 0.2941(12) 0.5581(11) 0.017(3) Uiso 1 1 d . . . H11 H 0.1455(17) 0.0980(12) 0.3078(12) 0.021(3) Uiso 1 1 d . . . H15 H 0.6321(16) 0.5425(12) 0.3542(11) 0.016(3) Uiso 1 1 d . . . H17 H 0.6880(17) 0.1803(12) 0.3418(11) 0.019(3) Uiso 1 1 d . . . Cl1 Cl 0.71616(18) 0.39961(16) 0.05465(18) 0.03091(16) Uani 0.776(3) 1 d PDU A 1 C21 C 0.55804(16) 0.50149(13) 0.06057(10) 0.0230(3) Uani 0.776(3) 1 d PDU . 1 H21A H 0.4864 0.4749 0.1086 0.028 Uiso 0.776(3) 1 calc PR A 1 H21B H 0.6185 0.5856 0.0942 0.028 Uiso 0.776(3) 1 calc PR A 1 Cl2 Cl 0.6869(8) 0.3783(7) 0.0552(7) 0.0448(12) Uani 0.224(3) 1 d PDU A 2 C22 C 0.5195(6) 0.4442(4) -0.0342(4) 0.0241(9) Uani 0.224(3) 1 d PDU . 2 H22A H 0.5578 0.4687 -0.0983 0.029 Uiso 0.224(3) 1 calc PR A 2 H22B H 0.4128 0.3829 -0.0657 0.029 Uiso 0.224(3) 1 calc PR A 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0287(3) 0.0290(3) 0.0156(3) 0.0000(2) -0.0039(2) 0.0021(3) O2 0.0252(3) 0.0185(3) 0.0224(3) 0.0084(2) 0.0066(2) -0.0004(2) O3 0.0152(2) 0.0190(3) 0.0255(3) -0.0007(2) 0.0077(2) -0.0026(2) S1 0.01590(8) 0.02048(9) 0.01495(8) 0.00411(7) -0.00039(6) 0.00326(6) S2 0.01319(7) 0.01206(7) 0.01713(8) 0.00065(6) 0.00415(6) -0.00199(5) S3 0.01200(7) 0.01311(8) 0.01859(9) 0.00173(6) 0.00471(6) 0.00147(5) C1 0.0112(3) 0.0136(3) 0.0130(3) 0.0014(2) 0.0026(2) 0.0006(2) C2 0.0111(3) 0.0160(3) 0.0129(3) 0.0024(2) 0.0025(2) 0.0008(2) C3 0.0136(3) 0.0166(3) 0.0124(3) 0.0019(2) 0.0024(2) 0.0018(2) C4 0.0135(3) 0.0173(3) 0.0132(3) 0.0024(2) 0.0022(2) 0.0003(2) C5 0.0139(3) 0.0180(3) 0.0161(3) 0.0030(3) 0.0024(2) 0.0030(2) C6 0.0167(3) 0.0192(3) 0.0137(3) 0.0012(3) 0.0029(2) -0.0020(2) C7 0.0260(4) 0.0199(4) 0.0185(4) 0.0007(3) 0.0073(3) 0.0024(3) C8 0.0110(2) 0.0133(3) 0.0122(3) 0.0007(2) 0.0029(2) 0.0004(2) C9 0.0111(2) 0.0132(3) 0.0124(3) 0.0010(2) 0.0027(2) -0.0004(2) C10 0.0120(3) 0.0124(3) 0.0142(3) 0.0013(2) 0.0036(2) 0.0003(2) C11 0.0124(3) 0.0154(3) 0.0147(3) 0.0003(2) 0.0025(2) -0.0011(2) C12 0.0159(3) 0.0150(3) 0.0151(3) 0.0027(2) 0.0044(2) 0.0018(2) C13 0.0230(4) 0.0262(4) 0.0166(4) 0.0057(3) -0.0005(3) -0.0050(3) C14 0.0115(3) 0.0126(3) 0.0120(3) 0.0013(2) 0.0025(2) 0.0003(2) C15 0.0137(3) 0.0120(3) 0.0143(3) 0.0011(2) 0.0039(2) 0.0004(2) C16 0.0138(3) 0.0116(3) 0.0144(3) 0.0007(2) 0.0042(2) 0.0001(2) C17 0.0135(3) 0.0123(3) 0.0169(3) 0.0021(2) 0.0039(2) 0.0006(2) C18 0.0162(3) 0.0136(3) 0.0162(3) 0.0000(2) 0.0052(2) -0.0019(2) C19 0.0242(4) 0.0137(3) 0.0305(5) 0.0037(3) 0.0095(3) 0.0005(3) Cl1 0.0297(3) 0.0391(4) 0.0243(2) 0.0059(2) 0.0030(2) 0.0185(3) C21 0.0211(5) 0.0308(6) 0.0178(5) 0.0053(4) 0.0047(4) 0.0081(4) Cl2 0.053(2) 0.057(3) 0.0271(9) 0.0060(16) 0.0075(16) 0.0317(18) C22 0.0217(15) 0.0304(17) 0.0198(15) 0.0055(13) 0.0041(12) 0.0055(13) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C6 1.2285(10) . ? O2 C12 1.2280(10) . ? O3 C18 1.2301(10) . ? S1 C5 1.7108(9) . ? S1 C4 1.7296(8) . ? S2 C11 1.7146(8) . ? S2 C10 1.7250(8) . ? S3 C17 1.7055(8) . ? S3 C16 1.7229(8) . ? C1 C2 1.5178(11) . ? C1 C8 1.5207(11) . ? C1 C14 1.5224(10) . ? C1 H1 0.9800 . ? C2 C5 1.3756(11) . ? C2 C3 1.4276(11) . ? C3 C4 1.3793(11) . ? C3 H3 0.907(14) . ? C4 C6 1.4713(12) . ? C5 H5 0.941(14) . ? C6 C7 1.5013(13) . ? C7 H7A 0.9600 . ? C7 H7B 0.9600 . ? C7 H7C 0.9600 . ? C8 C11 1.3753(11) . ? C8 C9 1.4229(10) . ? C9 C10 1.3785(11) . ? C9 H9 0.931(13) . ? C10 C12 1.4679(11) . ? C11 H11 0.942(13) . ? C12 C13 1.5034(12) . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? C14 C17 1.3762(11) . ? C14 C15 1.4217(11) . ? C15 C16 1.3823(11) . ? C15 H15 0.884(13) . ? C16 C18 1.4658(11) . ? C17 H17 0.943(13) . ? C18 C19 1.5037(12) . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? Cl1 C21 1.786(2) . ? C21 C21 1.506(2) 2_665 ? C21 H21A 0.9700 . ? C21 H21B 0.9700 . ? Cl2 C22 1.767(6) . ? C22 C22 1.498(8) 2_665 ? C22 H22A 0.9700 . ? C22 H22B 0.9700 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C5 S1 C4 91.49(4) . . ? C11 S2 C10 91.57(4) . . ? C17 S3 C16 91.84(4) . . ? C2 C1 C8 113.62(6) . . ? C2 C1 C14 109.83(6) . . ? C8 C1 C14 111.39(6) . . ? C2 C1 H1 107.2 . . ? C8 C1 H1 107.2 . . ? C14 C1 H1 107.2 . . ? C5 C2 C3 111.47(7) . . ? C5 C2 C1 123.30(7) . . ? C3 C2 C1 125.17(7) . . ? C4 C3 C2 112.74(7) . . ? C4 C3 H3 122.8(9) . . ? C2 C3 H3 124.4(9) . . ? C3 C4 C6 130.30(8) . . ? C3 C4 S1 111.40(6) . . ? C6 C4 S1 118.26(6) . . ? C2 C5 S1 112.91(6) . . ? C2 C5 H5 126.6(8) . . ? S1 C5 H5 120.5(8) . . ? O1 C6 C4 119.57(8) . . ? O1 C6 C7 121.09(8) . . ? C4 C6 C7 119.34(7) . . ? C6 C7 H7A 109.5 . . ? C6 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C6 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C11 C8 C9 111.51(7) . . ? C11 C8 C1 126.22(7) . . ? C9 C8 C1 122.23(6) . . ? C10 C9 C8 112.97(7) . . ? C10 C9 H9 125.0(8) . . ? C8 C9 H9 122.0(8) . . ? C9 C10 C12 128.83(7) . . ? C9 C10 S2 111.32(6) . . ? C12 C10 S2 119.85(6) . . ? C8 C11 S2 112.63(6) . . ? C8 C11 H11 129.0(8) . . ? S2 C11 H11 118.4(8) . . ? O2 C12 C10 120.73(7) . . ? O2 C12 C13 120.63(8) . . ? C10 C12 C13 118.64(7) . . ? C12 C13 H13A 109.5 . . ? C12 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C12 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C17 C14 C15 111.49(7) . . ? C17 C14 C1 124.51(7) . . ? C15 C14 C1 123.94(7) . . ? C16 C15 C14 112.86(7) . . ? C16 C15 H15 123.0(8) . . ? C14 C15 H15 124.1(8) . . ? C15 C16 C18 130.34(7) . . ? C15 C16 S3 111.09(6) . . ? C18 C16 S3 118.52(6) . . ? C14 C17 S3 112.71(6) . . ? C14 C17 H17 129.0(8) . . ? S3 C17 H17 118.2(8) . . ? O3 C18 C16 120.12(8) . . ? O3 C18 C19 121.33(7) . . ? C16 C18 C19 118.52(7) . . ? C18 C19 H19A 109.5 . . ? C18 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C18 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C21 C21 Cl1 108.73(13) 2_665 . ? C21 C21 H21A 109.9 2_665 . ? Cl1 C21 H21A 109.9 . . ? C21 C21 H21B 109.9 2_665 . ? Cl1 C21 H21B 109.9 . . ? H21A C21 H21B 108.3 . . ? C22 C22 Cl2 110.2(5) 2_665 . ? C22 C22 H22A 109.6 2_665 . ? Cl2 C22 H22A 109.6 . . ? C22 C22 H22B 109.6 2_665 . ? Cl2 C22 H22B 109.6 . . ? H22A C22 H22B 108.1 . . ? 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 C8 C1 C2 C5 125.98(8) . . . . ? C14 C1 C2 C5 -108.51(8) . . . . ? C8 C1 C2 C3 -57.12(10) . . . . ? C14 C1 C2 C3 68.39(9) . . . . ? C5 C2 C3 C4 -0.31(10) . . . . ? C1 C2 C3 C4 -177.53(7) . . . . ? C2 C3 C4 C6 -177.19(8) . . . . ? C2 C3 C4 S1 0.51(9) . . . . ? C5 S1 C4 C3 -0.45(6) . . . . ? C5 S1 C4 C6 177.56(7) . . . . ? C3 C2 C5 S1 -0.04(9) . . . . ? C1 C2 C5 S1 177.24(6) . . . . ? C4 S1 C5 C2 0.28(7) . . . . ? C3 C4 C6 O1 178.20(9) . . . . ? S1 C4 C6 O1 0.63(11) . . . . ? C3 C4 C6 C7 -1.82(13) . . . . ? S1 C4 C6 C7 -179.39(6) . . . . ? C2 C1 C8 C11 -13.89(11) . . . . ? C14 C1 C8 C11 -138.57(8) . . . . ? C2 C1 C8 C9 168.61(7) . . . . ? C14 C1 C8 C9 43.93(10) . . . . ? C11 C8 C9 C10 -0.11(10) . . . . ? C1 C8 C9 C10 177.73(7) . . . . ? C8 C9 C10 C12 179.67(7) . . . . ? C8 C9 C10 S2 0.09(9) . . . . ? C11 S2 C10 C9 -0.04(6) . . . . ? C11 S2 C10 C12 -179.66(7) . . . . ? C9 C8 C11 S2 0.07(9) . . . . ? C1 C8 C11 S2 -177.65(6) . . . . ? C10 S2 C11 C8 -0.02(6) . . . . ? C9 C10 C12 O2 179.15(8) . . . . ? S2 C10 C12 O2 -1.30(11) . . . . ? C9 C10 C12 C13 -1.43(13) . . . . ? S2 C10 C12 C13 178.12(7) . . . . ? C2 C1 C14 C17 -83.13(9) . . . . ? C8 C1 C14 C17 43.65(10) . . . . ? C2 C1 C14 C15 93.80(9) . . . . ? C8 C1 C14 C15 -139.42(7) . . . . ? C17 C14 C15 C16 0.52(10) . . . . ? C1 C14 C15 C16 -176.76(7) . . . . ? C14 C15 C16 C18 177.02(8) . . . . ? C14 C15 C16 S3 -0.43(9) . . . . ? C17 S3 C16 C15 0.17(6) . . . . ? C17 S3 C16 C18 -177.61(7) . . . . ? C15 C14 C17 S3 -0.39(9) . . . . ? C1 C14 C17 S3 176.88(6) . . . . ? C16 S3 C17 C14 0.13(6) . . . . ? C15 C16 C18 O3 -178.45(8) . . . . ? S3 C16 C18 O3 -1.17(11) . . . . ? C15 C16 C18 C19 -0.39(13) . . . . ? S3 C16 C18 C19 176.90(6) . . . . ? H1 C1 C14 C17 160.7 . . . . ? H1 C1 C8 C11 104.4 . . . . ? H1 C1 C2 C5 7.7 . . . . ? _diffrn_measured_fraction_theta_max 0.979 _diffrn_reflns_theta_full 38.99 _diffrn_measured_fraction_theta_full 0.979 _refine_diff_density_max 0.618 _refine_diff_density_min -0.509 _refine_diff_density_rms 0.070 # Attachment 'compounds2-2e.cif' data_2 _database_code_depnum_ccdc_archive 'CCDC 677784' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety "2(C19H16O3S3) C2h4Cl2'" _chemical_formula_sum 'C40 H36 Cl2 O6 S6' _chemical_formula_weight 875.95 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.9859(8) _cell_length_b 10.9220(11) _cell_length_c 12.2218(13) _cell_angle_alpha 97.398(2) _cell_angle_beta 106.184(2) _cell_angle_gamma 96.687(2) _cell_volume 1002.17(18) _cell_formula_units_Z 1 _cell_measurement_temperature 125(2) _cell_measurement_reflns_used 4123 _cell_measurement_theta_min 1.76 _cell_measurement_theta_max 28.50 _exptl_crystal_description plate _exptl_crystal_colour 'pale yellow' _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.451 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 454 _exptl_absorpt_coefficient_mu 0.521 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8186 _exptl_absorpt_correction_T_max 0.9497 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 125(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 'Bruker SMART 1000 CCD' _diffrn_measurement_method '/w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12146 _diffrn_reflns_av_R_equivalents 0.0198 _diffrn_reflns_av_sigmaI/netI 0.0252 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.76 _diffrn_reflns_theta_max 29.60 _reflns_number_total 5512 _reflns_number_gt 4724 _reflns_threshold_expression >2sigma(I) _computing_data_collection SMART _computing_cell_refinement 'SAINT (Bruker 2001)' _computing_data_reduction 'SAINT (Bruker 2001)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _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^)+(0.0505P)^2^+0.3861P] 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 5512 _refine_ls_number_parameters 276 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0410 _refine_ls_R_factor_gt 0.0334 _refine_ls_wR_factor_ref 0.0931 _refine_ls_wR_factor_gt 0.0870 _refine_ls_goodness_of_fit_ref 1.044 _refine_ls_restrained_S_all 1.044 _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 O1 O 0.43600(16) 0.02907(10) 1.23121(10) 0.0302(2) Uani 1 1 d . . . O2 O 1.14015(14) 0.56838(10) 0.85463(10) 0.0284(2) Uani 1 1 d . . . O3 O 0.05330(17) 0.07321(12) 0.33005(10) 0.0368(3) Uani 1 1 d . . . S1 S 0.24115(4) 0.04046(3) 0.98681(3) 0.02109(8) Uani 1 1 d . . . S2 S 0.91675(4) 0.33267(3) 0.84915(3) 0.02106(8) Uani 1 1 d . . . S3 S 0.08790(5) 0.29112(4) 0.50626(3) 0.02593(9) Uani 1 1 d . . . C1 C 0.40255(17) 0.32114(12) 0.83392(11) 0.0186(2) Uani 1 1 d . . . H1 H 0.3646 0.3994 0.8642 0.022 Uiso 1 1 calc R . . C2 C 0.37175(17) 0.22464(12) 0.90821(11) 0.0180(2) Uani 1 1 d . . . C3 C 0.47953(17) 0.23252(12) 1.02402(11) 0.0182(2) Uani 1 1 d . . . C4 C 0.42521(17) 0.13919(12) 1.07779(11) 0.0187(2) Uani 1 1 d . . . C5 C 0.23787(18) 0.12444(13) 0.87757(12) 0.0208(3) Uani 1 1 d . . . C6 C 0.50270(19) 0.11638(13) 1.19556(12) 0.0218(3) Uani 1 1 d . . . C7 C 0.6664(2) 0.20183(16) 1.27135(13) 0.0325(3) Uani 1 1 d . . . H7A H 0.6588 0.2186 1.3504 0.049 Uiso 1 1 calc R . . H7B H 0.6771 0.2807 1.2418 0.049 Uiso 1 1 calc R . . H7C H 0.7702 0.1619 1.2713 0.049 Uiso 1 1 calc R . . C8 C 0.59743(17) 0.35302(12) 0.84412(11) 0.0180(2) Uani 1 1 d . . . C9 C 0.68418(17) 0.47628(12) 0.85061(11) 0.0193(2) Uani 1 1 d . . . H9 H 0.6283 0.5483 0.8530 0.023 Uiso 1 1 calc R . . C10 C 0.85843(18) 0.47960(12) 0.85305(11) 0.0192(2) Uani 1 1 d . . . C11 C 0.70967(18) 0.26682(13) 0.84338(12) 0.0203(2) Uani 1 1 d . . . C12 C 0.99111(19) 0.58539(13) 0.85457(12) 0.0223(3) Uani 1 1 d . . . C13 C 0.9369(2) 0.71247(14) 0.85192(15) 0.0310(3) Uani 1 1 d . . . H13A H 1.0416 0.7770 0.8849 0.047 Uiso 1 1 calc R . . H13B H 0.8542 0.7223 0.8973 0.047 Uiso 1 1 calc R . . H13C H 0.8795 0.7210 0.7718 0.047 Uiso 1 1 calc R . . C14 C 0.29536(17) 0.28291(13) 0.70761(11) 0.0196(2) Uani 1 1 d . . . C15 C 0.30200(18) 0.17164(13) 0.63432(12) 0.0208(3) Uani 1 1 d . . . C16 C 0.19527(17) 0.16325(13) 0.52268(12) 0.0213(3) Uani 1 1 d . . . C17 C 0.18432(18) 0.35492(14) 0.64874(12) 0.0226(3) Uani 1 1 d . . . C18 C 0.15748(19) 0.06306(14) 0.42206(12) 0.0248(3) Uani 1 1 d . . . C19 C 0.2473(2) -0.04910(15) 0.43421(13) 0.0296(3) Uani 1 1 d . . . H19A H 0.1635 -0.1243 0.3919 0.044 Uiso 1 1 calc R . . H19B H 0.2902 -0.0561 0.5161 0.044 Uiso 1 1 calc R . . H19C H 0.3473 -0.0405 0.4026 0.044 Uiso 1 1 calc R . . H17 H 0.161(2) 0.4321(17) 0.6771(15) 0.025(4) Uiso 1 1 d . . . H5 H 0.155(3) 0.0995(18) 0.8079(17) 0.030(5) Uiso 1 1 d . . . H15 H 0.361(2) 0.1116(18) 0.6567(16) 0.026(4) Uiso 1 1 d . . . H11 H 0.685(2) 0.1793(17) 0.8404(15) 0.026(4) Uiso 1 1 d . . . H3 H 0.572(3) 0.2948(18) 1.0562(16) 0.026(4) Uiso 1 1 d . . . Cl1 Cl 0.71402(12) 0.39821(10) 0.55491(7) 0.03799(17) Uani 0.77 1 d P A 1 C20 C 0.5578(3) 0.5010(2) 0.56022(18) 0.0337(4) Uani 0.77 1 d P . 1 H20A H 0.4848 0.4739 0.6089 0.040 Uiso 0.77 1 calc PR . 1 H20B H 0.6202 0.5870 0.5946 0.040 Uiso 0.77 1 calc PR . 1 Cl2 Cl 0.6736(5) 0.3679(3) 0.5540(3) 0.0440(10) Uiso 0.23 1 d P B 2 C21 C 0.5181(9) 0.4440(6) 0.4664(6) 0.0259(12) Uiso 0.23 1 d P . 2 H21A H 0.5633 0.4696 0.4038 0.031 Uiso 0.23 1 calc PR . 2 H21B H 0.4066 0.3848 0.4303 0.031 Uiso 0.23 1 calc PR . 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0335(6) 0.0261(5) 0.0313(6) 0.0104(4) 0.0099(5) -0.0009(4) O2 0.0209(5) 0.0265(5) 0.0355(6) -0.0010(4) 0.0106(4) -0.0041(4) O3 0.0371(7) 0.0392(6) 0.0232(5) -0.0009(5) -0.0043(5) 0.0021(5) S1 0.01750(16) 0.01841(15) 0.02513(17) 0.00110(12) 0.00632(12) -0.00302(11) S2 0.01602(15) 0.01984(15) 0.02665(17) 0.00266(12) 0.00645(12) 0.00139(11) S3 0.02096(17) 0.03016(18) 0.02272(17) 0.00544(13) -0.00021(13) 0.00397(13) C1 0.0145(6) 0.0208(6) 0.0189(6) 0.0029(5) 0.0035(4) 0.0011(4) C2 0.0139(6) 0.0196(6) 0.0194(6) 0.0016(4) 0.0048(4) 0.0011(4) C3 0.0141(6) 0.0193(6) 0.0197(6) 0.0009(5) 0.0046(5) -0.0001(4) C4 0.0153(6) 0.0191(6) 0.0204(6) 0.0011(5) 0.0054(5) 0.0005(4) C5 0.0158(6) 0.0226(6) 0.0209(6) 0.0011(5) 0.0033(5) -0.0007(5) C6 0.0215(6) 0.0214(6) 0.0228(6) 0.0041(5) 0.0075(5) 0.0024(5) C7 0.0296(8) 0.0377(8) 0.0225(7) 0.0075(6) -0.0006(6) -0.0068(6) C8 0.0159(6) 0.0191(6) 0.0171(5) 0.0018(4) 0.0036(4) -0.0002(4) C9 0.0181(6) 0.0189(6) 0.0186(6) 0.0015(5) 0.0041(5) -0.0005(5) C10 0.0191(6) 0.0172(6) 0.0197(6) 0.0013(4) 0.0051(5) -0.0001(4) C11 0.0174(6) 0.0188(6) 0.0231(6) 0.0026(5) 0.0054(5) -0.0007(5) C12 0.0215(6) 0.0205(6) 0.0222(6) -0.0004(5) 0.0068(5) -0.0033(5) C13 0.0317(8) 0.0198(6) 0.0408(8) 0.0042(6) 0.0121(7) -0.0013(6) C14 0.0140(6) 0.0234(6) 0.0200(6) 0.0038(5) 0.0041(5) 0.0000(5) C15 0.0163(6) 0.0246(6) 0.0200(6) 0.0039(5) 0.0040(5) 0.0009(5) C16 0.0159(6) 0.0248(6) 0.0212(6) 0.0045(5) 0.0037(5) -0.0004(5) C17 0.0176(6) 0.0259(7) 0.0225(6) 0.0036(5) 0.0036(5) 0.0026(5) C18 0.0211(7) 0.0285(7) 0.0217(6) 0.0028(5) 0.0053(5) -0.0037(5) C19 0.0319(8) 0.0288(7) 0.0263(7) 0.0009(6) 0.0088(6) 0.0019(6) Cl1 0.0344(4) 0.0476(5) 0.0317(3) 0.0070(3) 0.0039(3) 0.0200(4) C20 0.0288(10) 0.0450(12) 0.0282(10) 0.0067(9) 0.0076(8) 0.0116(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 O1 C6 1.2251(18) . ? O2 C12 1.2256(18) . ? O3 C18 1.2251(18) . ? S1 C5 1.7105(15) . ? S1 C4 1.7236(13) . ? S2 C11 1.7035(14) . ? S2 C10 1.7208(14) . ? S3 C17 1.7106(14) . ? S3 C16 1.7265(15) . ? C1 C14 1.5180(18) . ? C1 C2 1.5186(18) . ? C1 C8 1.5210(18) . ? C1 H1 1.0000 . ? C2 C5 1.3711(18) . ? C2 C3 1.4227(18) . ? C3 C4 1.3739(19) . ? C3 H3 0.90(2) . ? C4 C6 1.4658(19) . ? C5 H5 0.91(2) . ? C6 C7 1.502(2) . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C8 C11 1.3743(19) . ? C8 C9 1.4224(18) . ? C9 C10 1.3797(19) . ? C9 H9 0.9500 . ? C10 C12 1.4684(18) . ? C11 H11 0.947(19) . ? C12 C13 1.503(2) . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C14 C17 1.3693(19) . ? C14 C15 1.4293(19) . ? C15 C16 1.3777(19) . ? C15 H15 0.878(19) . ? C16 C18 1.473(2) . ? C17 H17 0.929(19) . ? C18 C19 1.493(2) . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? Cl1 C20 1.782(2) . ? C20 C20 1.500(4) 2_666 ? C20 H20A 0.9900 . ? C20 H20B 0.9900 . ? Cl2 C21 1.763(8) . ? C21 C21 1.488(13) 2_666 ? C21 H21A 0.9900 . ? C21 H21B 0.9900 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C5 S1 C4 91.53(7) . . ? C11 S2 C10 91.67(7) . . ? C17 S3 C16 91.40(7) . . ? C14 C1 C2 113.46(11) . . ? C14 C1 C8 109.86(10) . . ? C2 C1 C8 111.45(11) . . ? C14 C1 H1 107.3 . . ? C2 C1 H1 107.3 . . ? C8 C1 H1 107.3 . . ? C5 C2 C3 111.30(12) . . ? C5 C2 C1 126.41(12) . . ? C3 C2 C1 122.23(11) . . ? C4 C3 C2 113.13(12) . . ? C4 C3 H3 125.9(12) . . ? C2 C3 H3 121.0(12) . . ? C3 C4 C6 128.85(12) . . ? C3 C4 S1 111.22(10) . . ? C6 C4 S1 119.93(10) . . ? C2 C5 S1 112.82(10) . . ? C2 C5 H5 127.1(12) . . ? S1 C5 H5 120.0(12) . . ? O1 C6 C4 120.73(13) . . ? O1 C6 C7 120.70(13) . . ? C4 C6 C7 118.57(12) . . ? C6 C7 H7A 109.5 . . ? C6 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C6 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C11 C8 C9 111.57(12) . . ? C11 C8 C1 124.66(12) . . ? C9 C8 C1 123.72(12) . . ? C10 C9 C8 112.53(12) . . ? C10 C9 H9 123.7 . . ? C8 C9 H9 123.7 . . ? C9 C10 C12 130.09(13) . . ? C9 C10 S2 111.43(10) . . ? C12 C10 S2 118.45(10) . . ? C8 C11 S2 112.79(10) . . ? C8 C11 H11 128.3(12) . . ? S2 C11 H11 118.9(11) . . ? O2 C12 C10 120.12(13) . . ? O2 C12 C13 121.59(13) . . ? C10 C12 C13 118.25(13) . . ? C12 C13 H13A 109.5 . . ? C12 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C12 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C17 C14 C15 111.63(12) . . ? C17 C14 C1 123.29(12) . . ? C15 C14 C1 125.03(12) . . ? C16 C15 C14 112.44(13) . . ? C16 C15 H15 122.0(12) . . ? C14 C15 H15 125.4(12) . . ? C15 C16 C18 130.20(14) . . ? C15 C16 S3 111.59(11) . . ? C18 C16 S3 118.17(10) . . ? C14 C17 S3 112.94(11) . . ? C14 C17 H17 127.5(11) . . ? S3 C17 H17 119.5(11) . . ? O3 C18 C16 119.54(15) . . ? O3 C18 C19 121.21(14) . . ? C16 C18 C19 119.25(13) . . ? C18 C19 H19A 109.5 . . ? C18 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C18 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C20 C20 Cl1 108.9(2) 2_666 . ? C20 C20 H20A 109.9 2_666 . ? Cl1 C20 H20A 109.9 . . ? C20 C20 H20B 109.9 2_666 . ? Cl1 C20 H20B 109.9 . . ? H20A C20 H20B 108.3 . . ? C21 C21 Cl2 112.0(6) 2_666 . ? C21 C21 H21A 109.2 2_666 . ? Cl2 C21 H21A 109.2 . . ? C21 C21 H21B 109.2 2_666 . ? Cl2 C21 H21B 109.2 . . ? H21A C21 H21B 107.9 . . ? 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 C14 C1 C2 C5 -13.50(19) . . . . ? C8 C1 C2 C5 -138.15(13) . . . . ? C14 C1 C2 C3 169.45(12) . . . . ? C8 C1 C2 C3 44.81(16) . . . . ? C5 C2 C3 C4 -0.06(17) . . . . ? C1 C2 C3 C4 177.39(12) . . . . ? C2 C3 C4 C6 179.67(13) . . . . ? C2 C3 C4 S1 0.04(15) . . . . ? C5 S1 C4 C3 -0.01(11) . . . . ? C5 S1 C4 C6 -179.68(11) . . . . ? C3 C2 C5 S1 0.05(15) . . . . ? C1 C2 C5 S1 -177.27(10) . . . . ? C4 S1 C5 C2 -0.02(11) . . . . ? C3 C4 C6 O1 178.92(14) . . . . ? S1 C4 C6 O1 -1.48(19) . . . . ? C3 C4 C6 C7 -1.5(2) . . . . ? S1 C4 C6 C7 178.10(11) . . . . ? C14 C1 C8 C11 -83.29(16) . . . . ? C2 C1 C8 C11 43.35(17) . . . . ? C14 C1 C8 C9 93.85(14) . . . . ? C2 C1 C8 C9 -139.51(12) . . . . ? C11 C8 C9 C10 0.80(16) . . . . ? C1 C8 C9 C10 -176.68(12) . . . . ? C8 C9 C10 C12 177.13(13) . . . . ? C8 C9 C10 S2 -0.72(14) . . . . ? C11 S2 C10 C9 0.36(11) . . . . ? C11 S2 C10 C12 -177.77(11) . . . . ? C9 C8 C11 S2 -0.52(15) . . . . ? C1 C8 C11 S2 176.93(10) . . . . ? C10 S2 C11 C8 0.10(11) . . . . ? C9 C10 C12 O2 -178.68(14) . . . . ? S2 C10 C12 O2 -0.96(18) . . . . ? C9 C10 C12 C13 -0.7(2) . . . . ? S2 C10 C12 C13 176.97(11) . . . . ? C2 C1 C14 C17 124.82(14) . . . . ? C8 C1 C14 C17 -109.69(15) . . . . ? C2 C1 C14 C15 -57.83(17) . . . . ? C8 C1 C14 C15 67.67(16) . . . . ? C17 C14 C15 C16 -0.20(17) . . . . ? C1 C14 C15 C16 -177.82(12) . . . . ? C14 C15 C16 C18 -177.10(13) . . . . ? C14 C15 C16 S3 0.45(15) . . . . ? C17 S3 C16 C15 -0.46(11) . . . . ? C17 S3 C16 C18 177.42(11) . . . . ? C15 C14 C17 S3 -0.15(15) . . . . ? C1 C14 C17 S3 177.51(10) . . . . ? C16 S3 C17 C14 0.35(11) . . . . ? C15 C16 C18 O3 178.03(15) . . . . ? S3 C16 C18 O3 0.62(19) . . . . ? C15 C16 C18 C19 -2.0(2) . . . . ? S3 C16 C18 C19 -179.46(11) . . . . ? H1 C1 C2 C5 104.7 . . . . ? H1 C1 C8 C11 160.5 . . . . ? H1 C1 C14 C17 6.6 . . . . ? _diffrn_measured_fraction_theta_max 0.978 _diffrn_reflns_theta_full 29.60 _diffrn_measured_fraction_theta_full 0.978 _refine_diff_density_max 0.527 _refine_diff_density_min -0.472 _refine_diff_density_rms 0.066 data_2a _database_code_depnum_ccdc_archive 'CCDC 677785' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '2(C19H16O3S3) 0.26(C2H4Cl2)' _chemical_formula_sum 'C38.52 H33.03 Cl0.52 O6 S6' _chemical_formula_weight 802.71 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.925(3) _cell_length_b 10.805(5) _cell_length_c 11.946(5) _cell_angle_alpha 96.507(6) _cell_angle_beta 105.889(6) _cell_angle_gamma 96.037(6) _cell_volume 967.6(7) _cell_formula_units_Z 1 _cell_measurement_temperature 125(2) _cell_measurement_reflns_used 3225 _cell_measurement_theta_min 2.70 _cell_measurement_theta_max 23.21 _exptl_crystal_description plate _exptl_crystal_colour 'pale yellow' _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.378 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 417 _exptl_absorpt_coefficient_mu 0.434 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8735 _exptl_absorpt_correction_T_max 0.9661 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 125(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 'Bruker SMART 1000 CCD' _diffrn_measurement_method '/w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8231 _diffrn_reflns_av_R_equivalents 0.0731 _diffrn_reflns_av_sigmaI/netI 0.0867 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.79 _diffrn_reflns_theta_max 23.26 _reflns_number_total 2769 _reflns_number_gt 1966 _reflns_threshold_expression >2sigma(I) _computing_data_collection SMART _computing_cell_refinement 'SAINT (Bruker 2001)' _computing_data_reduction 'SAINT (Bruker 2001)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _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^)+(0.1001P)^2^+5.0402P] 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 2769 _refine_ls_number_parameters 243 _refine_ls_number_restraints 158 _refine_ls_R_factor_all 0.1206 _refine_ls_R_factor_gt 0.0872 _refine_ls_wR_factor_ref 0.2183 _refine_ls_wR_factor_gt 0.2038 _refine_ls_goodness_of_fit_ref 1.073 _refine_ls_restrained_S_all 1.104 _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 S1 S 0.2512(2) 0.04136(17) 0.49101(17) 0.0182(5) Uani 1 1 d U . . S2 S 0.9213(2) 0.33012(17) 0.34436(17) 0.0200(5) Uani 1 1 d U . . S3 S 0.0902(3) 0.3011(2) -0.00007(18) 0.0283(6) Uani 1 1 d U . . C9 C 0.6881(9) 0.4760(7) 0.3437(6) 0.0153(16) Uani 1 1 d U . . H9 H 0.6313 0.5491 0.3447 0.018 Uiso 1 1 calc R . . O1 O 0.4399(7) 0.0345(5) 0.7417(5) 0.0282(13) Uani 1 1 d U . . O2 O 1.1447(6) 0.5671(5) 0.3520(4) 0.0231(12) Uani 1 1 d U . . O3 O 0.0326(8) 0.0729(5) -0.1706(5) 0.0408(16) Uani 1 1 d U . . C1 C 0.4072(9) 0.3242(7) 0.3305(6) 0.0149(16) Uani 1 1 d U . . H1 H 0.3693 0.4035 0.3609 0.018 Uiso 1 1 calc R . . C2 C 0.3771(9) 0.2263(6) 0.4091(6) 0.0150(16) Uani 1 1 d U . . C3 C 0.4775(9) 0.2377(7) 0.5267(6) 0.0157(16) Uani 1 1 d U . . H3 H 0.5728 0.3035 0.5633 0.019 Uiso 1 1 calc R . . C4 C 0.4258(9) 0.1456(6) 0.5835(6) 0.0159(16) Uani 1 1 d U . . C5 C 0.2493(10) 0.1242(7) 0.3788(6) 0.0175(17) Uani 1 1 d U . . H5 H 0.1674 0.1017 0.3026 0.021 Uiso 1 1 calc R . . C6 C 0.4982(10) 0.1251(7) 0.7050(7) 0.0212(18) Uani 1 1 d U . . C7 C 0.6451(13) 0.2178(9) 0.7835(8) 0.047(3) Uani 1 1 d U . . H7A H 0.6228 0.2373 0.8599 0.071 Uiso 1 1 calc R . . H7B H 0.6533 0.2949 0.7482 0.071 Uiso 1 1 calc R . . H7C H 0.7566 0.1827 0.7946 0.071 Uiso 1 1 calc R . . C8 C 0.6013(9) 0.3535(6) 0.3394(6) 0.0146(16) Uani 1 1 d U . . C10 C 0.8625(9) 0.4786(7) 0.3462(6) 0.0165(16) Uani 1 1 d U . . C11 C 0.7131(9) 0.2669(7) 0.3394(6) 0.0179(17) Uani 1 1 d U . . H11 H 0.6787 0.1794 0.3369 0.021 Uiso 1 1 calc R . . C12 C 0.9937(10) 0.5838(7) 0.3510(6) 0.0185(17) Uani 1 1 d U . . C13 C 0.9404(11) 0.7123(7) 0.3496(7) 0.030(2) Uani 1 1 d U . . H13A H 1.0465 0.7753 0.3691 0.045 Uiso 1 1 calc R . . H13B H 0.8754 0.7277 0.4076 0.045 Uiso 1 1 calc R . . H13C H 0.8642 0.7183 0.2711 0.045 Uiso 1 1 calc R . . C14 C 0.2980(9) 0.2869(6) 0.2019(6) 0.0157(16) Uani 1 1 d U . . C15 C 0.2980(9) 0.1758(7) 0.1296(6) 0.0160(16) Uani 1 1 d U . . H15 H 0.3652 0.1116 0.1564 0.019 Uiso 1 1 calc R . . C16 C 0.1935(10) 0.1682(7) 0.0181(6) 0.0206(18) Uani 1 1 d U . . C17 C 0.1906(10) 0.3638(7) 0.1422(7) 0.0252(19) Uani 1 1 d U . . H17 H 0.1741 0.4435 0.1769 0.030 Uiso 1 1 calc R . . C18 C 0.1474(10) 0.0637(7) -0.0794(7) 0.0224(18) Uani 1 1 d U . . C19 C 0.2342(11) -0.0488(7) -0.0659(7) 0.029(2) Uani 1 1 d U . . H19A H 0.1556 -0.1215 -0.1175 0.043 Uiso 1 1 calc R . . H19B H 0.2600 -0.0638 0.0161 0.043 Uiso 1 1 calc R . . H19C H 0.3450 -0.0367 -0.0873 0.043 Uiso 1 1 calc R . . Cl1 Cl 0.2936(12) 0.6096(8) 0.9445(8) 0.040(4) Uani 0.258(9) 1 d PDU A 1 C32 C 0.441(5) 0.498(4) 0.9383(10) 0.076(14) Uiso 0.258(9) 1 d PD . 1 H32A H 0.3731 0.4124 0.9084 0.091 Uiso 0.258(9) 1 calc PR A 1 H32B H 0.5121 0.5185 0.8850 0.091 Uiso 0.258(9) 1 calc PR A 1 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 0.0077(9) 0.0185(10) 0.0280(10) -0.0017(7) 0.0083(8) -0.0022(7) S2 0.0075(9) 0.0208(10) 0.0319(11) 0.0009(8) 0.0076(8) 0.0016(7) S3 0.0170(10) 0.0328(11) 0.0297(11) 0.0014(8) -0.0010(8) 0.0035(8) C9 0.014(2) 0.016(2) 0.016(2) 0.0014(17) 0.0046(18) 0.0027(17) O1 0.027(2) 0.027(2) 0.031(2) 0.0066(16) 0.0098(16) 0.0024(16) O2 0.0170(19) 0.025(2) 0.027(2) 0.0001(15) 0.0089(16) -0.0006(15) O3 0.040(2) 0.040(2) 0.039(2) 0.0053(17) 0.0063(17) 0.0025(17) C1 0.013(2) 0.015(2) 0.017(2) 0.0013(17) 0.0047(17) 0.0029(17) C2 0.012(2) 0.017(2) 0.018(2) 0.0003(17) 0.0068(18) 0.0022(17) C3 0.014(2) 0.016(2) 0.017(2) -0.0010(17) 0.0058(18) 0.0025(17) C4 0.013(2) 0.017(2) 0.018(2) 0.0000(17) 0.0057(18) 0.0033(17) C5 0.015(2) 0.018(2) 0.018(2) 0.0001(17) 0.0052(18) 0.0024(18) C6 0.019(2) 0.021(2) 0.024(2) 0.0028(18) 0.0074(18) 0.0016(18) C7 0.047(3) 0.048(3) 0.045(3) 0.011(2) 0.012(2) 0.001(2) C8 0.013(2) 0.016(2) 0.014(2) 0.0005(17) 0.0040(17) 0.0021(17) C10 0.015(2) 0.018(2) 0.017(2) 0.0000(17) 0.0062(18) 0.0015(18) C11 0.016(2) 0.018(2) 0.019(2) 0.0027(18) 0.0057(18) 0.0006(18) C12 0.016(2) 0.020(2) 0.019(2) -0.0005(18) 0.0073(18) 0.0006(18) C13 0.029(3) 0.029(3) 0.032(3) 0.0032(18) 0.0111(19) 0.0003(18) C14 0.013(2) 0.018(2) 0.017(2) 0.0024(17) 0.0059(18) 0.0015(17) C15 0.013(2) 0.018(2) 0.017(2) 0.0026(17) 0.0055(18) -0.0001(17) C16 0.018(2) 0.022(2) 0.022(2) 0.0028(18) 0.0066(18) 0.0005(18) C17 0.024(2) 0.025(2) 0.027(2) 0.0041(18) 0.0074(18) 0.0015(18) C18 0.022(2) 0.024(2) 0.022(2) 0.0046(18) 0.0064(18) 0.0003(18) C19 0.028(3) 0.030(3) 0.028(3) 0.0024(18) 0.0094(19) 0.0028(19) Cl1 0.039(4) 0.042(4) 0.041(4) 0.0050(19) 0.010(2) 0.0121(19) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 C5 1.692(7) . ? S1 C4 1.719(7) . ? S2 C11 1.701(7) . ? S2 C10 1.716(7) . ? S3 C17 1.693(8) . ? S3 C16 1.732(8) . ? C9 C10 1.372(10) . ? C9 C8 1.415(10) . ? O1 C6 1.216(9) . ? O2 C12 1.227(9) . ? O3 C18 1.235(9) . ? C1 C8 1.509(10) . ? C1 C14 1.527(10) . ? C1 C2 1.533(10) . ? C2 C5 1.360(10) . ? C2 C3 1.396(10) . ? C3 C4 1.356(10) . ? C4 C6 1.459(10) . ? C6 C7 1.477(12) . ? C8 C11 1.355(10) . ? C10 C12 1.443(10) . ? C12 C13 1.494(11) . ? C14 C17 1.368(10) . ? C14 C15 1.397(10) . ? C15 C16 1.351(10) . ? C16 C18 1.466(11) . ? C18 C19 1.462(11) . ? Cl1 C32 1.775(11) . ? C32 C32 1.509(11) 2_667 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C5 S1 C4 91.0(4) . . ? C11 S2 C10 91.4(4) . . ? C17 S3 C16 91.1(4) . . ? C10 C9 C8 113.2(6) . . ? C8 C1 C14 110.2(6) . . ? C8 C1 C2 111.1(6) . . ? C14 C1 C2 113.6(6) . . ? C5 C2 C3 111.5(6) . . ? C5 C2 C1 126.4(6) . . ? C3 C2 C1 122.0(6) . . ? C4 C3 C2 113.4(6) . . ? C3 C4 C6 129.4(7) . . ? C3 C4 S1 111.1(5) . . ? C6 C4 S1 119.4(5) . . ? C2 C5 S1 112.9(6) . . ? O1 C6 C4 121.3(7) . . ? O1 C6 C7 120.3(7) . . ? C4 C6 C7 118.4(7) . . ? C11 C8 C9 111.1(6) . . ? C11 C8 C1 125.1(6) . . ? C9 C8 C1 123.8(6) . . ? C9 C10 C12 129.8(7) . . ? C9 C10 S2 110.9(5) . . ? C12 C10 S2 119.2(5) . . ? C8 C11 S2 113.3(5) . . ? O2 C12 C10 120.3(7) . . ? O2 C12 C13 120.7(7) . . ? C10 C12 C13 118.9(7) . . ? C17 C14 C15 111.7(7) . . ? C17 C14 C1 122.5(7) . . ? C15 C14 C1 125.8(6) . . ? C16 C15 C14 113.7(7) . . ? C15 C16 C18 129.8(7) . . ? C15 C16 S3 110.9(5) . . ? C18 C16 S3 119.1(6) . . ? C14 C17 S3 112.6(6) . . ? O3 C18 C19 121.8(7) . . ? O3 C18 C16 118.4(7) . . ? C19 C18 C16 119.8(7) . . ? C32 C32 Cl1 107.2(13) 2_667 . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 23.26 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.767 _refine_diff_density_min -0.538 _refine_diff_density_rms 0.122 data_2b _database_code_depnum_ccdc_archive 'CCDC 677786' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '2(C19H16O3S3) 0.24(C2H4Cl2)' _chemical_formula_sum 'C38.48 H32.96 Cl0.48 O6 S6' _chemical_formula_weight 800.74 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.944(4) _cell_length_b 10.813(6) _cell_length_c 11.977(6) _cell_angle_alpha 96.448(7) _cell_angle_beta 105.998(7) _cell_angle_gamma 95.975(7) _cell_volume 972.9(9) _cell_formula_units_Z 1 _cell_measurement_temperature 125(2) _cell_measurement_reflns_used 2945 _cell_measurement_theta_min 1.79 _cell_measurement_theta_max 21.82 _exptl_crystal_description plate _exptl_crystal_colour 'pale yellow' _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.367 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 416 _exptl_absorpt_coefficient_mu 0.429 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.9040 _exptl_absorpt_correction_T_max 0.9665 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 125(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 'Bruker SMART 1000 CCD' _diffrn_measurement_method '/w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9319 _diffrn_reflns_av_R_equivalents 0.0619 _diffrn_reflns_av_sigmaI/netI 0.0754 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.79 _diffrn_reflns_theta_max 24.71 _reflns_number_total 3310 _reflns_number_gt 2274 _reflns_threshold_expression >2sigma(I) _computing_data_collection SMART _computing_cell_refinement 'SAINT (Bruker 2001)' _computing_data_reduction 'SAINT (Bruker 2001)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _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^)+(0.0922P)^2^+2.2601P] 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 3310 _refine_ls_number_parameters 243 _refine_ls_number_restraints 154 _refine_ls_R_factor_all 0.1113 _refine_ls_R_factor_gt 0.0725 _refine_ls_wR_factor_ref 0.1966 _refine_ls_wR_factor_gt 0.1753 _refine_ls_goodness_of_fit_ref 1.091 _refine_ls_restrained_S_all 1.152 _refine_ls_shift/su_max 0.005 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.07871(16) 0.67008(13) 0.65577(13) 0.0256(3) Uani 1 1 d U . . S2 S 0.74837(16) 0.95868(12) 0.50875(12) 0.0245(3) Uani 1 1 d U . . S3 S 0.90991(19) 0.69847(15) 1.00031(13) 0.0342(4) Uani 1 1 d U . . O1 O -0.1451(5) 0.4334(4) 0.6478(3) 0.0302(9) Uani 1 1 d U . . O2 O 0.5599(5) 0.9649(4) 0.2574(4) 0.0352(10) Uani 1 1 d U . . O3 O 0.9671(6) 0.9273(4) 1.1709(4) 0.0439(11) Uani 1 1 d U . . C1 C 0.5936(6) 0.6754(5) 0.6698(4) 0.0209(11) Uani 1 1 d U . . H1 H 0.6311 0.5958 0.6398 0.025 Uiso 1 1 calc R . . C2 C 0.3977(6) 0.6468(5) 0.6612(4) 0.0200(11) Uani 1 1 d U . . C3 C 0.3122(6) 0.5235(5) 0.6568(4) 0.0210(11) Uani 1 1 d U . . H3 H 0.3693 0.4506 0.6561 0.025 Uiso 1 1 calc R . . C4 C 0.1381(7) 0.5212(5) 0.6537(5) 0.0236(12) Uani 1 1 d U . . C5 C 0.2869(6) 0.7344(5) 0.6610(4) 0.0219(11) Uani 1 1 d U . . H5 H 0.3214 0.8216 0.6634 0.026 Uiso 1 1 calc R . . C6 C 0.0053(7) 0.4153(5) 0.6495(5) 0.0249(12) Uani 1 1 d U . . C7 C 0.0604(8) 0.2868(5) 0.6510(5) 0.0349(14) Uani 1 1 d U . . H7A H -0.0446 0.2236 0.6335 0.052 Uiso 1 1 calc R . . H7B H 0.1394 0.2818 0.7287 0.052 Uiso 1 1 calc R . . H7C H 0.1225 0.2712 0.5916 0.052 Uiso 1 1 calc R . . C8 C 0.7013(6) 0.7128(5) 0.7977(5) 0.0216(11) Uani 1 1 d U . . C9 C 0.7012(7) 0.8241(5) 0.8702(5) 0.0230(12) Uani 1 1 d U . . H9 H 0.6332 0.8881 0.8438 0.028 Uiso 1 1 calc R . . C10 C 0.8080(7) 0.8317(5) 0.9821(5) 0.0265(12) Uani 1 1 d U . . C11 C 0.8085(7) 0.6359(5) 0.8578(5) 0.0283(13) Uani 1 1 d U . . H11 H 0.8245 0.5561 0.8234 0.034 Uiso 1 1 calc R . . C12 C 0.8538(7) 0.9356(5) 1.0799(5) 0.0293(13) Uani 1 1 d U . . C13 C 0.7658(8) 1.0481(6) 1.0661(5) 0.0356(14) Uani 1 1 d U . . H13A H 0.6673 1.0419 1.1006 0.053 Uiso 1 1 calc R . . H13B H 0.7206 1.0545 0.9825 0.053 Uiso 1 1 calc R . . H13C H 0.8507 1.1229 1.1062 0.053 Uiso 1 1 calc R . . C14 C 0.6235(6) 0.7733(5) 0.5914(4) 0.0187(11) Uani 1 1 d U . . C15 C 0.5230(6) 0.7620(5) 0.4733(4) 0.0213(11) Uani 1 1 d U . . H15 H 0.4286 0.6959 0.4366 0.026 Uiso 1 1 calc R . . C16 C 0.5738(6) 0.8550(5) 0.4161(5) 0.0207(11) Uani 1 1 d U . . C17 C 0.7499(7) 0.8765(5) 0.6212(5) 0.0242(12) Uani 1 1 d U . . H17 H 0.8307 0.9000 0.6975 0.029 Uiso 1 1 calc R . . C18 C 0.5019(7) 0.8744(5) 0.2950(5) 0.0276(13) Uani 1 1 d U . . C19 C 0.3555(9) 0.7797(7) 0.2151(6) 0.0497(17) Uani 1 1 d U . . H19A H 0.2418 0.8094 0.2108 0.075 Uiso 1 1 calc R . . H19B H 0.3573 0.6994 0.2457 0.075 Uiso 1 1 calc R . . H19C H 0.3715 0.7683 0.1365 0.075 Uiso 1 1 calc R . . Cl1 Cl 0.2899(15) 0.6081(12) 0.9445(10) 0.0473(18) Uani 0.15 1 d PD A 1 C21 C 0.4404(18) 0.5009(10) 0.9394(6) 0.031(9) Uiso 0.15 1 d PD . 1 H21A H 0.3748 0.4157 0.9063 0.037 Uiso 0.15 1 calc PR . 1 H21B H 0.5122 0.5253 0.8876 0.037 Uiso 0.15 1 calc PR . 1 Cl2 Cl 0.2958(18) 0.6146(10) 0.9445(6) 0.0473(18) Uani 0.09 1 d PRD . 2 C22 C 0.4782(18) 0.5598(10) 1.0271(6) 0.044(17) Uiso 0.09 1 d PRD . 2 H22A H 0.5817 0.6257 1.0432 0.052 Uiso 0.09 1 calc PR . 2 H22B H 0.4593 0.5466 1.1035 0.052 Uiso 0.09 1 calc PR . 2 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 0.0106(6) 0.0258(7) 0.0420(8) 0.0029(6) 0.0125(5) -0.0010(5) S2 0.0134(6) 0.0239(7) 0.0368(8) 0.0004(6) 0.0129(5) -0.0061(5) S3 0.0210(7) 0.0400(8) 0.0355(8) 0.0039(6) 0.0008(6) -0.0006(6) O1 0.0175(16) 0.0326(18) 0.0392(19) -0.0001(15) 0.0116(14) -0.0057(14) O2 0.0312(18) 0.0350(19) 0.043(2) 0.0116(16) 0.0160(16) -0.0019(16) O3 0.043(2) 0.042(2) 0.039(2) 0.0054(17) 0.0037(17) -0.0034(17) C1 0.014(2) 0.024(2) 0.026(2) 0.0022(18) 0.0087(17) 0.0000(17) C2 0.015(2) 0.022(2) 0.023(2) 0.0012(17) 0.0088(17) -0.0022(17) C3 0.015(2) 0.025(2) 0.024(2) 0.0026(18) 0.0081(17) 0.0001(17) C4 0.019(2) 0.026(2) 0.027(2) 0.0017(18) 0.0105(18) -0.0002(18) C5 0.016(2) 0.023(2) 0.028(2) 0.0018(18) 0.0102(17) -0.0021(17) C6 0.018(2) 0.028(2) 0.030(2) 0.0013(18) 0.0113(18) -0.0027(18) C7 0.030(2) 0.034(2) 0.042(2) 0.004(2) 0.016(2) -0.004(2) C8 0.0116(19) 0.028(2) 0.027(2) 0.0037(18) 0.0106(17) -0.0016(17) C9 0.016(2) 0.027(2) 0.027(2) 0.0025(18) 0.0103(17) -0.0019(17) C10 0.019(2) 0.030(2) 0.031(2) 0.0030(19) 0.0102(18) -0.0008(18) C11 0.022(2) 0.028(2) 0.034(2) 0.0025(19) 0.0093(19) -0.0029(18) C12 0.026(2) 0.033(2) 0.029(2) 0.0052(19) 0.0102(19) -0.0057(19) C13 0.034(2) 0.038(2) 0.034(2) 0.001(2) 0.014(2) 0.000(2) C14 0.0095(18) 0.021(2) 0.028(2) 0.0021(17) 0.0114(17) 0.0011(16) C15 0.014(2) 0.022(2) 0.028(2) 0.0006(18) 0.0093(17) -0.0012(17) C16 0.0131(19) 0.022(2) 0.028(2) 0.0006(18) 0.0095(17) -0.0001(17) C17 0.015(2) 0.027(2) 0.030(2) -0.0006(18) 0.0090(18) -0.0007(18) C18 0.020(2) 0.031(2) 0.034(2) 0.0041(19) 0.0113(18) 0.0005(19) C19 0.047(3) 0.052(3) 0.045(3) 0.016(2) 0.007(2) -0.010(2) Cl1 0.036(3) 0.065(5) 0.043(4) 0.006(3) 0.009(3) 0.027(3) Cl2 0.036(3) 0.065(5) 0.043(4) 0.006(3) 0.009(3) 0.027(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 S1 C5 1.708(5) . ? S1 C4 1.723(6) . ? S2 C17 1.693(6) . ? S2 C16 1.721(5) . ? S3 C11 1.700(6) . ? S3 C10 1.731(6) . ? O1 C6 1.226(6) . ? O2 C18 1.223(7) . ? O3 C12 1.226(7) . ? C1 C8 1.519(7) . ? C1 C2 1.528(7) . ? C1 C14 1.534(7) . ? C2 C5 1.357(7) . ? C2 C3 1.421(7) . ? C3 C4 1.371(7) . ? C4 C6 1.460(7) . ? C6 C7 1.500(8) . ? C8 C11 1.371(8) . ? C8 C9 1.404(7) . ? C9 C10 1.362(7) . ? C10 C12 1.466(8) . ? C12 C13 1.467(8) . ? C14 C17 1.364(7) . ? C14 C15 1.404(7) . ? C15 C16 1.366(7) . ? C16 C18 1.452(8) . ? C18 C19 1.495(8) . ? Cl1 C21 1.758(9) . ? C21 C21 1.503(10) 2_667 ? Cl2 C22 1.7169 . ? C22 C22 1.498(10) 2_667 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C5 S1 C4 91.6(3) . . ? C17 S2 C16 91.3(3) . . ? C11 S3 C10 91.1(3) . . ? C8 C1 C2 109.7(4) . . ? C8 C1 C14 113.5(4) . . ? C2 C1 C14 110.9(4) . . ? C5 C2 C3 112.2(4) . . ? C5 C2 C1 124.9(5) . . ? C3 C2 C1 122.8(4) . . ? C4 C3 C2 112.5(5) . . ? C3 C4 C6 130.0(5) . . ? C3 C4 S1 111.2(4) . . ? C6 C4 S1 118.8(4) . . ? C2 C5 S1 112.5(4) . . ? O1 C6 C4 119.9(5) . . ? O1 C6 C7 121.9(5) . . ? C4 C6 C7 118.2(5) . . ? C11 C8 C9 111.4(5) . . ? C11 C8 C1 122.3(5) . . ? C9 C8 C1 126.2(5) . . ? C10 C9 C8 113.6(5) . . ? C9 C10 C12 129.9(5) . . ? C9 C10 S3 111.0(4) . . ? C12 C10 S3 119.0(4) . . ? C8 C11 S3 112.9(4) . . ? O3 C12 C10 119.2(5) . . ? O3 C12 C13 121.4(5) . . ? C10 C12 C13 119.4(5) . . ? C17 C14 C15 111.0(5) . . ? C17 C14 C1 127.0(5) . . ? C15 C14 C1 122.0(4) . . ? C16 C15 C14 113.6(4) . . ? C15 C16 C18 129.4(5) . . ? C15 C16 S2 110.8(4) . . ? C18 C16 S2 119.9(4) . . ? C14 C17 S2 113.3(4) . . ? O2 C18 C16 121.5(5) . . ? O2 C18 C19 119.8(5) . . ? C16 C18 C19 118.7(5) . . ? C21 C21 Cl1 110.1(7) 2_667 . ? C22 C22 Cl2 115.5(5) 2_667 . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 24.71 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.608 _refine_diff_density_min -0.761 _refine_diff_density_rms 0.111 data_2c _database_code_depnum_ccdc_archive 'CCDC 677787' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '2(C19H16O3S3) 0.24(C2H4Cl2)' _chemical_formula_sum 'C38.48 H32.95 Cl0.48 O6 S6' _chemical_formula_weight 800.73 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.931(2) _cell_length_b 10.798(3) _cell_length_c 11.948(3) _cell_angle_alpha 96.264(4) _cell_angle_beta 105.987(3) _cell_angle_gamma 95.939(3) _cell_volume 968.2(4) _cell_formula_units_Z 1 _cell_measurement_temperature 125(2) _cell_measurement_reflns_used 4042 _cell_measurement_theta_min 2.70 _cell_measurement_theta_max 23.68 _exptl_crystal_description plate _exptl_crystal_colour 'pale yellow' _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.373 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 416 _exptl_absorpt_coefficient_mu 0.431 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8743 _exptl_absorpt_correction_T_max 0.9663 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 125(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 'Bruker SMART 1000 CCD' _diffrn_measurement_method '/w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10217 _diffrn_reflns_av_R_equivalents 0.0382 _diffrn_reflns_av_sigmaI/netI 0.0479 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.70 _diffrn_reflns_theta_max 26.37 _reflns_number_total 3926 _reflns_number_gt 3129 _reflns_threshold_expression >2sigma(I) _computing_data_collection SMART _computing_cell_refinement 'SAINT (Bruker 2001)' _computing_data_reduction 'SAINT (Bruker 2001)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _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^)+(0.0499P)^2^+2.3287P] 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 3926 _refine_ls_number_parameters 261 _refine_ls_number_restraints 151 _refine_ls_R_factor_all 0.0824 _refine_ls_R_factor_gt 0.0625 _refine_ls_wR_factor_ref 0.1511 _refine_ls_wR_factor_gt 0.1421 _refine_ls_goodness_of_fit_ref 1.156 _refine_ls_restrained_S_all 1.166 _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 O1 O -0.6459(3) -0.0665(2) 0.1478(2) 0.0266(6) Uani 1 1 d U . . O2 O 0.0592(4) 0.4648(3) -0.2430(3) 0.0297(7) Uani 1 1 d U . . O3 O 0.4668(4) 0.4266(3) 0.6716(3) 0.0402(8) Uani 1 1 d U . . S1 S -0.42124(12) 0.17016(8) 0.15601(9) 0.0215(2) Uani 1 1 d U . . S2 S 0.24828(11) 0.45869(8) 0.00856(8) 0.0200(2) Uani 1 1 d U . . S3 S 0.40994(13) 0.19839(10) 0.50051(9) 0.0299(3) Uani 1 1 d U . . C1 C 0.0939(4) 0.1761(3) 0.1701(3) 0.0168(7) Uani 1 1 d U . . H1 H 0.1316 0.0966 0.1399 0.020 Uiso 1 1 calc R . . C2 C -0.1017(4) 0.1468(3) 0.1611(3) 0.0159(7) Uani 1 1 d U . . C3 C -0.1869(4) 0.0230(3) 0.1567(3) 0.0170(7) Uani 1 1 d U . . H3 H -0.1298 -0.0501 0.1555 0.020 Uiso 1 1 calc R . . C4 C -0.3621(5) 0.0214(3) 0.1543(3) 0.0174(7) Uani 1 1 d U . . C5 C -0.2132(5) 0.2339(3) 0.1610(3) 0.0181(7) Uani 1 1 d U . . C6 C -0.4957(5) -0.0842(3) 0.1494(3) 0.0198(8) Uani 1 1 d U . . C7 C -0.4391(6) -0.2129(4) 0.1512(4) 0.0306(9) Uani 1 1 d U . . H7A H -0.3595 -0.2177 0.2291 0.046 Uiso 1 1 calc R . . H7B H -0.3773 -0.2284 0.0916 0.046 Uiso 1 1 calc R . . H7C H -0.5438 -0.2766 0.1342 0.046 Uiso 1 1 calc R . . C8 C 0.1230(4) 0.2732(3) 0.0916(3) 0.0160(7) Uani 1 1 d U . . C9 C 0.0219(4) 0.2619(3) -0.0265(3) 0.0166(7) Uani 1 1 d U . . C10 C 0.0736(4) 0.3548(3) -0.0841(3) 0.0174(7) Uani 1 1 d U . . C11 C 0.2502(5) 0.3761(3) 0.1225(3) 0.0195(8) Uani 1 1 d U . . C12 C 0.0025(5) 0.3743(4) -0.2058(3) 0.0231(8) Uani 1 1 d U . . C13 C -0.1453(7) 0.2800(5) -0.2848(4) 0.0472(13) Uani 1 1 d U . . H13A H -0.2590 0.3082 -0.2854 0.071 Uiso 1 1 calc R . . H13B H -0.1398 0.1985 -0.2560 0.071 Uiso 1 1 calc R . . H13C H -0.1340 0.2714 -0.3648 0.071 Uiso 1 1 calc R . . C14 C 0.2016(4) 0.2120(3) 0.2981(3) 0.0174(7) Uani 1 1 d U . . C15 C 0.2012(5) 0.3250(3) 0.3705(3) 0.0195(8) Uani 1 1 d U . . H15 H 0.1334 0.3892 0.3439 0.023 Uiso 1 1 calc R . . C16 C 0.3093(5) 0.3315(3) 0.4829(3) 0.0213(8) Uani 1 1 d U . . C17 C 0.3079(5) 0.1359(4) 0.3574(3) 0.0236(8) Uani 1 1 d U . . C18 C 0.3549(5) 0.4352(4) 0.5806(3) 0.0242(8) Uani 1 1 d U . . C19 C 0.2658(6) 0.5484(4) 0.5664(4) 0.0305(9) Uani 1 1 d U . . H19A H 0.1650 0.5410 0.5988 0.046 Uiso 1 1 calc R . . H19B H 0.2237 0.5562 0.4826 0.046 Uiso 1 1 calc R . . H19C H 0.3496 0.6231 0.6082 0.046 Uiso 1 1 calc R . . H5 H -0.188(5) 0.328(4) 0.166(3) 0.013(9) Uiso 1 1 d . . . H9 H -0.072(5) 0.196(4) -0.061(3) 0.013(9) Uiso 1 1 d . . . H11 H 0.327(5) 0.406(3) 0.193(3) 0.010(9) Uiso 1 1 d . . . H17 H 0.330(5) 0.060(4) 0.330(3) 0.019(10) Uiso 1 1 d . . . Cl1 Cl 0.7817(13) 1.0978(10) 0.4443(8) 0.032(3) Uiso 0.14 1 d PD A 1 C20 C 0.941(4) 0.997(3) 0.443(3) 0.031(6) Uiso 0.14 1 d PD . 1 H20A H 0.8808 0.9096 0.4145 0.037 Uiso 0.14 1 calc PR . 1 H20B H 1.0078 1.0211 0.3882 0.037 Uiso 0.14 1 calc PR . 1 Cl2 Cl 1.1887(18) 0.8704(14) 0.5549(11) 0.032(4) Uiso 0.10 1 d PD B 2 C21 C 1.024(5) 0.945(4) 0.469(4) 0.037(10) Uiso 0.10 1 d PD . 2 H21A H 1.0631 0.9710 0.4027 0.045 Uiso 0.10 1 calc PR . 2 H21B H 0.9155 0.8825 0.4358 0.045 Uiso 0.10 1 calc PR . 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0150(13) 0.0264(14) 0.0357(15) -0.0043(11) 0.0099(11) -0.0069(10) O2 0.0295(15) 0.0246(14) 0.0373(16) 0.0110(12) 0.0128(13) -0.0012(11) O3 0.0442(18) 0.0344(16) 0.0282(16) 0.0006(13) -0.0055(14) -0.0085(14) S1 0.0120(4) 0.0185(4) 0.0339(5) 0.0015(4) 0.0079(4) -0.0006(3) S2 0.0143(4) 0.0160(4) 0.0283(5) -0.0006(4) 0.0081(4) -0.0048(3) S3 0.0217(5) 0.0333(6) 0.0269(5) 0.0033(4) -0.0040(4) 0.0003(4) C1 0.0102(15) 0.0179(16) 0.0210(17) 0.0014(13) 0.0031(13) 0.0022(13) C2 0.0112(15) 0.0178(16) 0.0152(16) -0.0015(13) 0.0016(13) -0.0040(13) C3 0.0116(15) 0.0200(17) 0.0172(16) 0.0013(13) 0.0026(13) -0.0020(13) C4 0.0144(16) 0.0152(16) 0.0219(17) -0.0004(13) 0.0065(13) -0.0004(13) C5 0.0126(16) 0.0181(17) 0.0223(18) -0.0004(14) 0.0061(13) -0.0029(13) C6 0.0184(17) 0.0185(17) 0.0207(18) -0.0023(14) 0.0068(14) -0.0033(14) C7 0.030(2) 0.0218(18) 0.041(2) 0.0029(16) 0.0141(18) -0.0037(16) C8 0.0074(15) 0.0181(16) 0.0232(17) 0.0004(13) 0.0068(13) 0.0013(12) C9 0.0111(15) 0.0169(16) 0.0217(18) 0.0002(13) 0.0060(13) 0.0002(13) C10 0.0074(15) 0.0163(16) 0.0269(18) 0.0004(14) 0.0044(13) -0.0010(12) C11 0.0122(16) 0.0206(17) 0.0233(19) -0.0019(14) 0.0042(14) -0.0006(13) C12 0.0152(17) 0.0239(18) 0.031(2) 0.0077(15) 0.0070(15) 0.0004(14) C13 0.043(2) 0.053(3) 0.031(2) 0.019(2) -0.0075(19) -0.020(2) C14 0.0091(15) 0.0200(17) 0.0229(18) 0.0024(14) 0.0057(13) -0.0003(13) C15 0.0124(16) 0.0243(18) 0.0208(17) 0.0026(14) 0.0056(14) -0.0041(13) C16 0.0156(16) 0.0235(18) 0.0236(18) 0.0042(15) 0.0058(14) -0.0045(14) C17 0.0194(18) 0.0230(19) 0.0255(19) 0.0018(15) 0.0042(15) -0.0020(15) C18 0.0236(18) 0.0259(18) 0.0181(18) 0.0028(14) 0.0035(15) -0.0123(15) C19 0.032(2) 0.031(2) 0.027(2) -0.0011(16) 0.0106(17) -0.0038(17) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C6 1.221(4) . ? O2 C12 1.211(4) . ? O3 C18 1.219(5) . ? S1 C5 1.703(3) . ? S1 C4 1.719(4) . ? S2 C11 1.704(4) . ? S2 C10 1.722(3) . ? S3 C17 1.705(4) . ? S3 C16 1.720(4) . ? C1 C14 1.517(5) . ? C1 C8 1.523(5) . ? C1 C2 1.522(5) . ? C1 H1 1.0000 . ? C2 C5 1.356(5) . ? C2 C3 1.423(5) . ? C3 C4 1.380(5) . ? C3 H3 0.9500 . ? C4 C6 1.459(5) . ? C5 H5 1.01(4) . ? C6 C7 1.505(5) . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C8 C11 1.364(5) . ? C8 C9 1.403(5) . ? C9 C10 1.368(5) . ? C9 H9 0.95(4) . ? C10 C12 1.455(5) . ? C11 H11 0.90(4) . ? C12 C13 1.496(6) . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C14 C17 1.353(5) . ? C14 C15 1.417(5) . ? C15 C16 1.370(5) . ? C15 H15 0.9500 . ? C16 C18 1.465(5) . ? C17 H17 0.90(4) . ? C18 C19 1.476(6) . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? Cl1 C20 1.75(2) . ? C20 C20 1.42(6) 2_776 ? C20 H20A 0.9900 . ? C20 H20B 0.9900 . ? Cl2 C21 1.75(3) . ? C21 C21 1.47(9) 2_776 ? C21 H21A 0.9900 . ? C21 H21B 0.9900 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C5 S1 C4 91.54(17) . . ? C11 S2 C10 91.41(18) . . ? C17 S3 C16 91.36(19) . . ? C14 C1 C8 114.1(3) . . ? C14 C1 C2 109.9(3) . . ? C8 C1 C2 110.9(3) . . ? C14 C1 H1 107.2 . . ? C8 C1 H1 107.2 . . ? C2 C1 H1 107.2 . . ? C5 C2 C3 112.0(3) . . ? C5 C2 C1 124.9(3) . . ? C3 C2 C1 123.0(3) . . ? C4 C3 C2 112.1(3) . . ? C4 C3 H3 123.9 . . ? C2 C3 H3 123.9 . . ? C3 C4 C6 130.0(3) . . ? C3 C4 S1 111.3(3) . . ? C6 C4 S1 118.7(3) . . ? C2 C5 S1 113.0(3) . . ? C2 C5 H5 129(2) . . ? S1 C5 H5 118(2) . . ? O1 C6 C4 120.4(3) . . ? O1 C6 C7 122.0(3) . . ? C4 C6 C7 117.6(3) . . ? C6 C7 H7A 109.5 . . ? C6 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C6 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C11 C8 C9 111.8(3) . . ? C11 C8 C1 126.1(3) . . ? C9 C8 C1 122.0(3) . . ? C10 C9 C8 113.4(3) . . ? C10 C9 H9 124(2) . . ? C8 C9 H9 122(2) . . ? C9 C10 C12 129.4(3) . . ? C9 C10 S2 110.9(3) . . ? C12 C10 S2 119.7(3) . . ? C8 C11 S2 112.5(3) . . ? C8 C11 H11 129(2) . . ? S2 C11 H11 119(2) . . ? O2 C12 C10 121.5(3) . . ? O2 C12 C13 120.2(4) . . ? C10 C12 C13 118.2(3) . . ? C12 C13 H13A 109.5 . . ? C12 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C12 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C17 C14 C15 112.0(3) . . ? C17 C14 C1 122.7(3) . . ? C15 C14 C1 125.3(3) . . ? C16 C15 C14 112.7(3) . . ? C16 C15 H15 123.7 . . ? C14 C15 H15 123.7 . . ? C15 C16 C18 129.3(4) . . ? C15 C16 S3 111.2(3) . . ? C18 C16 S3 119.3(3) . . ? C14 C17 S3 112.8(3) . . ? C14 C17 H17 128(3) . . ? S3 C17 H17 119(3) . . ? O3 C18 C16 119.2(4) . . ? O3 C18 C19 121.4(4) . . ? C16 C18 C19 119.3(3) . . ? C18 C19 H19A 109.5 . . ? C18 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C18 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C20 C20 Cl1 111(3) 2_776 . ? C20 C20 H20A 109.5 2_776 . ? Cl1 C20 H20A 109.5 . . ? C20 C20 H20B 109.5 2_776 . ? Cl1 C20 H20B 109.5 . . ? H20A C20 H20B 108.0 . . ? C21 C21 Cl2 116(4) 2_776 . ? C21 C21 H21A 108.3 2_776 . ? Cl2 C21 H21A 108.3 . . ? C21 C21 H21B 108.3 2_776 . ? Cl2 C21 H21B 108.3 . . ? H21A C21 H21B 107.4 . . ? 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 C14 C1 C2 C5 83.6(4) . . . . ? C8 C1 C2 C5 -43.6(5) . . . . ? C14 C1 C2 C3 -93.7(4) . . . . ? C8 C1 C2 C3 139.2(3) . . . . ? C5 C2 C3 C4 -0.5(4) . . . . ? C1 C2 C3 C4 177.1(3) . . . . ? C2 C3 C4 C6 179.8(4) . . . . ? C2 C3 C4 S1 0.6(4) . . . . ? C5 S1 C4 C3 -0.5(3) . . . . ? C5 S1 C4 C6 -179.7(3) . . . . ? C3 C2 C5 S1 0.1(4) . . . . ? C1 C2 C5 S1 -177.4(3) . . . . ? C4 S1 C5 C2 0.2(3) . . . . ? C3 C4 C6 O1 -179.9(4) . . . . ? S1 C4 C6 O1 -0.8(5) . . . . ? C3 C4 C6 C7 2.5(6) . . . . ? S1 C4 C6 C7 -178.4(3) . . . . ? C14 C1 C8 C11 9.5(5) . . . . ? C2 C1 C8 C11 134.3(4) . . . . ? C14 C1 C8 C9 -173.5(3) . . . . ? C2 C1 C8 C9 -48.7(4) . . . . ? C11 C8 C9 C10 0.5(4) . . . . ? C1 C8 C9 C10 -176.9(3) . . . . ? C8 C9 C10 C12 179.6(3) . . . . ? C8 C9 C10 S2 -0.5(4) . . . . ? C11 S2 C10 C9 0.3(3) . . . . ? C11 S2 C10 C12 -179.8(3) . . . . ? C9 C8 C11 S2 -0.3(4) . . . . ? C1 C8 C11 S2 176.9(3) . . . . ? C10 S2 C11 C8 0.0(3) . . . . ? C9 C10 C12 O2 177.2(4) . . . . ? S2 C10 C12 O2 -2.6(5) . . . . ? C9 C10 C12 C13 -2.1(6) . . . . ? S2 C10 C12 C13 178.1(3) . . . . ? C8 C1 C14 C17 -126.5(4) . . . . ? C2 C1 C14 C17 108.2(4) . . . . ? C8 C1 C14 C15 55.1(4) . . . . ? C2 C1 C14 C15 -70.2(4) . . . . ? C17 C14 C15 C16 0.5(4) . . . . ? C1 C14 C15 C16 179.1(3) . . . . ? C14 C15 C16 C18 175.0(3) . . . . ? C14 C15 C16 S3 -0.6(4) . . . . ? C17 S3 C16 C15 0.4(3) . . . . ? C17 S3 C16 C18 -175.7(3) . . . . ? C15 C14 C17 S3 -0.2(4) . . . . ? C1 C14 C17 S3 -178.8(3) . . . . ? C16 S3 C17 C14 -0.1(3) . . . . ? C15 C16 C18 O3 -173.5(4) . . . . ? S3 C16 C18 O3 1.8(5) . . . . ? C15 C16 C18 C19 6.0(6) . . . . ? S3 C16 C18 C19 -178.7(3) . . . . ? H1 C1 C2 C5 -160.3 . . . . ? H1 C1 C8 C11 -109.0 . . . . ? H1 C1 C14 C17 -8.0 . . . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 26.37 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.640 _refine_diff_density_min -0.481 _refine_diff_density_rms 0.087 data_2d _database_code_depnum_ccdc_archive 'CCDC 677788' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '2(C19H16O3S3) 0.21(C2H4Cl2)' _chemical_formula_sum 'C38.42 H32.84 Cl0.42 O6 S6' _chemical_formula_weight 797.78 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.964(4) _cell_length_b 10.792(5) _cell_length_c 12.002(6) _cell_angle_alpha 96.368(6) _cell_angle_beta 106.028(6) _cell_angle_gamma 95.933(6) _cell_volume 975.6(8) _cell_formula_units_Z 1 _cell_measurement_temperature 125(2) _cell_measurement_reflns_used 7143 _cell_measurement_theta_min 2.69 _cell_measurement_theta_max 24.48 _exptl_crystal_description plate _exptl_crystal_colour 'pale yellow' _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.358 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 415 _exptl_absorpt_coefficient_mu 0.424 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8834 _exptl_absorpt_correction_T_max 0.9791 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 125(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 'Bruker SMART 1000 CCD' _diffrn_measurement_method '/w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10240 _diffrn_reflns_av_R_equivalents 0.0587 _diffrn_reflns_av_sigmaI/netI 0.0675 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.69 _diffrn_reflns_theta_max 26.37 _reflns_number_total 3934 _reflns_number_gt 3092 _reflns_threshold_expression >2sigma(I) _computing_data_collection SMART _computing_cell_refinement 'SAINT (Bruker 2001)' _computing_data_reduction 'SAINT (Bruker 2001)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _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^)+(0.0634P)^2^+5.4700P] 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 3934 _refine_ls_number_parameters 247 _refine_ls_number_restraints 154 _refine_ls_R_factor_all 0.1134 _refine_ls_R_factor_gt 0.0903 _refine_ls_wR_factor_ref 0.2275 _refine_ls_wR_factor_gt 0.2144 _refine_ls_goodness_of_fit_ref 1.195 _refine_ls_restrained_S_all 1.204 _refine_ls_shift/su_max 0.006 _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 O1 O -0.6456(5) -0.0667(4) 0.1479(4) 0.0290(9) Uani 1 1 d U . . O2 O 0.0601(6) 0.4643(4) -0.2431(4) 0.0325(10) Uani 1 1 d U . . O3 O 0.4681(6) 0.4268(4) 0.6716(4) 0.0424(11) Uani 1 1 d U . . S1 S -0.42138(17) 0.17047(13) 0.15613(13) 0.0240(4) Uani 1 1 d U . . S2 S 0.24744(17) 0.45841(12) 0.00871(13) 0.0227(3) Uani 1 1 d U . . S3 S 0.4103(2) 0.19770(16) 0.50041(14) 0.0339(4) Uani 1 1 d U . . C1 C 0.0937(6) 0.1756(5) 0.1706(4) 0.0164(10) Uani 1 1 d U . . H1 H 0.1311 0.0959 0.1406 0.020 Uiso 1 1 calc R . . C2 C -0.1025(6) 0.1465(5) 0.1616(4) 0.0184(10) Uani 1 1 d U . . C3 C -0.1879(6) 0.0232(5) 0.1571(4) 0.0186(10) Uani 1 1 d U . . H3 H -0.1314 -0.0501 0.1557 0.022 Uiso 1 1 calc R . . C4 C -0.3618(7) 0.0216(5) 0.1550(5) 0.0193(11) Uani 1 1 d U . . C5 C -0.2133(7) 0.2339(5) 0.1614(5) 0.0197(11) Uani 1 1 d U . . H5 H -0.1788 0.3213 0.1639 0.024 Uiso 1 1 calc R . . C6 C -0.4952(7) -0.0847(5) 0.1493(5) 0.0217(11) Uani 1 1 d U . . C7 C -0.4404(8) -0.2136(6) 0.1504(6) 0.0332(14) Uani 1 1 d U . . H7A H -0.5457 -0.2773 0.1261 0.050 Uiso 1 1 calc R . . H7B H -0.3703 -0.2216 0.2298 0.050 Uiso 1 1 calc R . . H7C H -0.3695 -0.2263 0.0962 0.050 Uiso 1 1 calc R . . C8 C 0.1227(6) 0.2730(5) 0.0919(5) 0.0175(10) Uani 1 1 d U . . C9 C 0.0219(6) 0.2611(5) -0.0267(5) 0.0194(11) Uani 1 1 d U . . H9 H -0.0724 0.1950 -0.0630 0.023 Uiso 1 1 calc R . . C10 C 0.0733(6) 0.3544(5) -0.0844(5) 0.0190(11) Uani 1 1 d U . . C11 C 0.2493(7) 0.3766(5) 0.1221(5) 0.0208(11) Uani 1 1 d U . . H11 H 0.3295 0.4003 0.1984 0.025 Uiso 1 1 calc R . . C12 C 0.0027(7) 0.3737(5) -0.2061(5) 0.0258(12) Uani 1 1 d U . . C13 C -0.1444(10) 0.2797(7) -0.2854(6) 0.0477(18) Uani 1 1 d U . . H13A H -0.2576 0.3079 -0.2858 0.071 Uiso 1 1 calc R . . H13B H -0.1391 0.1979 -0.2574 0.071 Uiso 1 1 calc R . . H13C H -0.1330 0.2717 -0.3650 0.071 Uiso 1 1 calc R . . C14 C 0.2008(6) 0.2119(5) 0.2979(5) 0.0202(11) Uani 1 1 d U . . C15 C 0.2013(7) 0.3240(5) 0.3707(5) 0.0225(11) Uani 1 1 d U . . H15 H 0.1335 0.3883 0.3447 0.027 Uiso 1 1 calc R . . C16 C 0.3094(7) 0.3309(5) 0.4827(5) 0.0243(12) Uani 1 1 d U . . C17 C 0.3089(7) 0.1344(5) 0.3573(5) 0.0266(12) Uani 1 1 d U . . H17 H 0.3255 0.0548 0.3228 0.032 Uiso 1 1 calc R . . C18 C 0.3560(8) 0.4353(6) 0.5804(5) 0.0278(13) Uani 1 1 d U . . C19 C 0.2660(8) 0.5489(6) 0.5659(5) 0.0326(14) Uani 1 1 d U . . H19A H 0.3490 0.6239 0.6079 0.049 Uiso 1 1 calc R . . H19B H 0.1653 0.5412 0.5978 0.049 Uiso 1 1 calc R . . H19C H 0.2244 0.5566 0.4825 0.049 Uiso 1 1 calc R . . Cl1 Cl 0.780(3) 0.0947(19) 0.4463(16) 0.033(5) Uiso 0.10 1 d PD A 1 C20 C 0.940(4) -0.006(4) 0.4396(13) 0.019(10) Uiso 0.10 1 d PD . 1 H20A H 0.8830 -0.0939 0.4115 0.023 Uiso 0.10 1 calc PR . 1 H20B H 1.0066 0.0201 0.3855 0.023 Uiso 0.10 1 calc PR . 1 Cl2 Cl 0.808(2) 0.1256(18) 0.4438(15) 0.030(5) Uiso 0.11 1 d PD B 2 C21 C 0.982(8) 0.058(5) 0.531(3) 0.06(2) Uiso 0.11 1 d PD . 2 H21A H 1.0902 0.1207 0.5560 0.071 Uiso 0.11 1 calc PR . 2 H21B H 0.9520 0.0384 0.6025 0.071 Uiso 0.11 1 calc PR . 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0159(18) 0.029(2) 0.042(2) -0.0016(17) 0.0123(16) -0.0034(15) O2 0.030(2) 0.030(2) 0.042(2) 0.0126(17) 0.0146(18) 0.0019(17) O3 0.042(2) 0.041(2) 0.032(2) 0.0021(19) -0.0038(19) -0.0042(19) S1 0.0109(6) 0.0213(7) 0.0409(8) 0.0028(6) 0.0103(5) 0.0016(5) S2 0.0132(6) 0.0191(7) 0.0358(8) 0.0007(5) 0.0101(5) -0.0030(5) S3 0.0212(7) 0.0408(9) 0.0326(8) 0.0032(7) -0.0023(6) 0.0024(6) C1 0.010(2) 0.016(2) 0.022(2) 0.0011(18) 0.0032(18) 0.0017(17) C2 0.012(2) 0.022(2) 0.019(2) 0.0008(18) 0.0012(18) 0.0007(18) C3 0.012(2) 0.022(2) 0.020(2) 0.0009(18) 0.0042(18) 0.0007(18) C4 0.015(2) 0.017(2) 0.026(2) 0.0017(19) 0.0078(19) 0.0010(18) C5 0.012(2) 0.020(2) 0.026(2) 0.0020(19) 0.0068(19) -0.0006(18) C6 0.017(2) 0.022(2) 0.027(3) -0.0019(19) 0.011(2) -0.0028(19) C7 0.030(3) 0.025(3) 0.045(3) 0.003(2) 0.015(2) -0.004(2) C8 0.008(2) 0.020(2) 0.026(2) 0.0009(19) 0.0080(18) 0.0039(17) C9 0.011(2) 0.021(2) 0.027(3) -0.0004(19) 0.0075(19) 0.0020(18) C10 0.009(2) 0.017(2) 0.031(3) 0.0013(19) 0.0072(19) 0.0012(17) C11 0.011(2) 0.022(2) 0.028(3) -0.0004(19) 0.0053(19) 0.0009(18) C12 0.017(2) 0.027(3) 0.034(3) 0.005(2) 0.009(2) 0.002(2) C13 0.041(3) 0.052(3) 0.040(3) 0.017(3) -0.001(3) -0.014(3) C14 0.010(2) 0.023(2) 0.028(3) 0.006(2) 0.0060(19) 0.0022(18) C15 0.013(2) 0.027(3) 0.026(3) 0.003(2) 0.0065(19) -0.0032(19) C16 0.017(2) 0.027(3) 0.030(3) 0.004(2) 0.010(2) -0.0013(19) C17 0.021(2) 0.026(3) 0.031(3) 0.002(2) 0.006(2) 0.002(2) C18 0.025(3) 0.030(3) 0.025(3) 0.005(2) 0.007(2) -0.009(2) C19 0.031(3) 0.035(3) 0.030(3) -0.001(2) 0.009(2) -0.001(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 O1 C6 1.229(6) . ? O2 C12 1.217(7) . ? O3 C18 1.226(7) . ? S1 C5 1.708(5) . ? S1 C4 1.721(5) . ? S2 C11 1.700(6) . ? S2 C10 1.726(5) . ? S3 C17 1.711(6) . ? S3 C16 1.723(6) . ? C1 C14 1.515(7) . ? C1 C8 1.530(7) . ? C1 C2 1.533(7) . ? C2 C5 1.356(7) . ? C2 C3 1.419(7) . ? C3 C4 1.376(7) . ? C4 C6 1.463(7) . ? C6 C7 1.501(8) . ? C8 C11 1.369(7) . ? C8 C9 1.412(7) . ? C9 C10 1.373(7) . ? C10 C12 1.459(8) . ? C12 C13 1.494(9) . ? C14 C17 1.375(8) . ? C14 C15 1.410(8) . ? C15 C16 1.371(8) . ? C16 C18 1.470(8) . ? C18 C19 1.486(9) . ? Cl1 C20 1.770(10) . ? C20 C20 1.48(2) 2_756 ? Cl2 C21 1.769(10) . ? C21 C21 1.49(2) 2_756 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C5 S1 C4 91.2(2) . . ? C11 S2 C10 91.8(3) . . ? C17 S3 C16 91.5(3) . . ? C14 C1 C8 114.2(4) . . ? C14 C1 C2 109.8(4) . . ? C8 C1 C2 110.8(4) . . ? C5 C2 C3 111.9(5) . . ? C5 C2 C1 124.9(5) . . ? C3 C2 C1 123.1(4) . . ? C4 C3 C2 112.4(5) . . ? C3 C4 C6 129.8(5) . . ? C3 C4 S1 111.4(4) . . ? C6 C4 S1 118.7(4) . . ? C2 C5 S1 113.0(4) . . ? O1 C6 C4 120.1(5) . . ? O1 C6 C7 121.8(5) . . ? C4 C6 C7 118.1(5) . . ? C11 C8 C9 111.4(5) . . ? C11 C8 C1 126.4(5) . . ? C9 C8 C1 122.1(4) . . ? C10 C9 C8 113.5(5) . . ? C9 C10 C12 129.6(5) . . ? C9 C10 S2 110.5(4) . . ? C12 C10 S2 119.9(4) . . ? C8 C11 S2 112.8(4) . . ? O2 C12 C10 121.5(5) . . ? O2 C12 C13 120.0(6) . . ? C10 C12 C13 118.5(5) . . ? C17 C14 C15 111.7(5) . . ? C17 C14 C1 122.3(5) . . ? C15 C14 C1 126.0(5) . . ? C16 C15 C14 113.3(5) . . ? C15 C16 C18 129.5(5) . . ? C15 C16 S3 111.2(4) . . ? C18 C16 S3 119.1(4) . . ? C14 C17 S3 112.4(4) . . ? O3 C18 C16 119.4(6) . . ? O3 C18 C19 121.6(5) . . ? C16 C18 C19 119.0(5) . . ? C20 C20 Cl1 106.4(19) 2_756 . ? C21 C21 Cl2 113(2) 2_756 . ? 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 C14 C1 C2 C5 83.5(6) . . . . ? C8 C1 C2 C5 -43.5(7) . . . . ? C14 C1 C2 C3 -93.8(6) . . . . ? C8 C1 C2 C3 139.1(5) . . . . ? C5 C2 C3 C4 -0.7(7) . . . . ? C1 C2 C3 C4 177.0(5) . . . . ? C2 C3 C4 C6 179.3(5) . . . . ? C2 C3 C4 S1 1.0(6) . . . . ? C5 S1 C4 C3 -0.8(4) . . . . ? C5 S1 C4 C6 -179.3(4) . . . . ? C3 C2 C5 S1 0.1(6) . . . . ? C1 C2 C5 S1 -177.5(4) . . . . ? C4 S1 C5 C2 0.3(4) . . . . ? C3 C4 C6 O1 -179.8(5) . . . . ? S1 C4 C6 O1 -1.6(7) . . . . ? C3 C4 C6 C7 2.8(9) . . . . ? S1 C4 C6 C7 -179.0(4) . . . . ? C14 C1 C8 C11 9.4(7) . . . . ? C2 C1 C8 C11 134.0(5) . . . . ? C14 C1 C8 C9 -173.7(4) . . . . ? C2 C1 C8 C9 -49.1(6) . . . . ? C11 C8 C9 C10 0.4(6) . . . . ? C1 C8 C9 C10 -176.9(4) . . . . ? C8 C9 C10 C12 179.7(5) . . . . ? C8 C9 C10 S2 -0.3(6) . . . . ? C11 S2 C10 C9 0.1(4) . . . . ? C11 S2 C10 C12 -179.9(4) . . . . ? C9 C8 C11 S2 -0.3(6) . . . . ? C1 C8 C11 S2 176.8(4) . . . . ? C10 S2 C11 C8 0.1(4) . . . . ? C9 C10 C12 O2 177.6(5) . . . . ? S2 C10 C12 O2 -2.4(7) . . . . ? C9 C10 C12 C13 -1.8(9) . . . . ? S2 C10 C12 C13 178.2(5) . . . . ? C8 C1 C14 C17 -126.2(5) . . . . ? C2 C1 C14 C17 108.7(6) . . . . ? C8 C1 C14 C15 55.3(7) . . . . ? C2 C1 C14 C15 -69.8(6) . . . . ? C17 C14 C15 C16 0.5(7) . . . . ? C1 C14 C15 C16 179.2(5) . . . . ? C14 C15 C16 C18 174.6(5) . . . . ? C14 C15 C16 S3 -0.8(6) . . . . ? C17 S3 C16 C15 0.6(4) . . . . ? C17 S3 C16 C18 -175.3(4) . . . . ? C15 C14 C17 S3 0.0(6) . . . . ? C1 C14 C17 S3 -178.8(4) . . . . ? C16 S3 C17 C14 -0.3(4) . . . . ? C15 C16 C18 O3 -173.6(6) . . . . ? S3 C16 C18 O3 1.5(7) . . . . ? C15 C16 C18 C19 6.2(9) . . . . ? S3 C16 C18 C19 -178.7(4) . . . . ? H1 C1 C2 C5 -160.2 . . . . ? H1 C1 C8 C11 -109.2 . . . . ? H1 C1 C14 C17 -7.5 . . . . ? _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 26.37 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 1.042 _refine_diff_density_min -0.905 _refine_diff_density_rms 0.127 data_2e _database_code_depnum_ccdc_archive 'CCDC 677789' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '2(C19H16O3S3) 0.06(C2H4Cl2)' _chemical_formula_sum 'C38.12 H32.25 Cl0.12 O6 S6' _chemical_formula_weight 782.94 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.9498(16) _cell_length_b 10.739(2) _cell_length_c 11.936(2) _cell_angle_alpha 95.861(3) _cell_angle_beta 106.164(2) _cell_angle_gamma 95.609(3) _cell_volume 965.1(3) _cell_formula_units_Z 1 _cell_measurement_temperature 125(2) _cell_measurement_reflns_used 6915 _cell_measurement_theta_min 2.69 _cell_measurement_theta_max 25.48 _exptl_crystal_description plate _exptl_crystal_colour 'pale yellow' _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.347 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 407 _exptl_absorpt_coefficient_mu 0.407 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9378 _exptl_absorpt_correction_T_max 0.9799 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 125(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 'Bruker SMART 1000 CCD' _diffrn_measurement_method '/w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10955 _diffrn_reflns_av_R_equivalents 0.0412 _diffrn_reflns_av_sigmaI/netI 0.0530 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.69 _diffrn_reflns_theta_max 26.37 _reflns_number_total 3928 _reflns_number_gt 2850 _reflns_threshold_expression >2sigma(I) _computing_data_collection SMART _computing_cell_refinement 'SAINT (Bruker 2001)' _computing_data_reduction 'SAINT (Bruker 2001)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _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^)+(0.0512P)^2^+0.6540P] 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 3928 _refine_ls_number_parameters 258 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0726 _refine_ls_R_factor_gt 0.0440 _refine_ls_wR_factor_ref 0.1137 _refine_ls_wR_factor_gt 0.1015 _refine_ls_goodness_of_fit_ref 1.047 _refine_ls_restrained_S_all 1.047 _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 O1 O -0.6469(2) -0.06601(18) 0.64833(18) 0.0286(5) Uani 1 1 d . . . O2 O 0.0597(3) 0.46199(19) 0.25391(18) 0.0306(5) Uani 1 1 d . . . O3 O 0.4752(3) 0.4260(2) 1.17112(18) 0.0396(6) Uani 1 1 d . . . S1 S -0.42197(9) 0.17193(6) 0.65829(7) 0.02293(18) Uani 1 1 d . . . S2 S 0.24390(9) 0.45818(6) 0.50719(6) 0.02103(18) Uani 1 1 d . . . S3 S 0.41080(10) 0.19434(7) 1.00251(7) 0.0296(2) Uani 1 1 d . . . C1 C 0.0915(3) 0.1749(2) 0.6718(2) 0.0182(6) Uani 1 1 d . . . H1 H 0.1285 0.0948 0.6419 0.022 Uiso 1 1 calc R . . C2 C -0.1037(3) 0.1464(2) 0.6635(2) 0.0163(5) Uani 1 1 d . . . C3 C -0.1894(3) 0.0238(3) 0.6591(2) 0.0178(6) Uani 1 1 d . . . C4 C -0.3634(3) 0.0223(2) 0.6563(2) 0.0187(6) Uani 1 1 d . . . C5 C -0.2148(3) 0.2347(3) 0.6625(2) 0.0203(6) Uani 1 1 d . . . C6 C -0.4964(4) -0.0836(3) 0.6509(2) 0.0217(6) Uani 1 1 d . . . C7 C -0.4412(4) -0.2132(3) 0.6525(3) 0.0321(7) Uani 1 1 d . . . H7A H -0.3625 -0.2195 0.7305 0.048 Uiso 1 1 calc R . . H7B H -0.3790 -0.2284 0.5931 0.048 Uiso 1 1 calc R . . H7C H -0.5461 -0.2763 0.6348 0.048 Uiso 1 1 calc R . . C8 C 0.1211(3) 0.2716(2) 0.5928(2) 0.0167(5) Uani 1 1 d . . . C9 C 0.0224(3) 0.2595(3) 0.4731(2) 0.0180(6) Uani 1 1 d . . . C10 C 0.0730(3) 0.3522(2) 0.4145(2) 0.0180(6) Uani 1 1 d . . . C11 C 0.2464(3) 0.3763(3) 0.6224(3) 0.0210(6) Uani 1 1 d . . . C12 C 0.0039(3) 0.3702(3) 0.2916(2) 0.0224(6) Uani 1 1 d . . . C13 C -0.1385(5) 0.2727(3) 0.2120(3) 0.0443(9) Uani 1 1 d . . . H13A H -0.2539 0.3015 0.2044 0.066 Uiso 1 1 calc R . . H13B H -0.1354 0.1930 0.2453 0.066 Uiso 1 1 calc R . . H13C H -0.1194 0.2599 0.1342 0.066 Uiso 1 1 calc R . . C14 C 0.1994(3) 0.2096(3) 0.7992(2) 0.0186(6) Uani 1 1 d . . . C15 C 0.2020(3) 0.3231(3) 0.8717(2) 0.0207(6) Uani 1 1 d . . . H15 H 0.1346 0.3884 0.8450 0.025 Uiso 1 1 calc R . . C16 C 0.3109(3) 0.3296(3) 0.9839(2) 0.0218(6) Uani 1 1 d . . . C17 C 0.3070(4) 0.1319(3) 0.8595(3) 0.0246(6) Uani 1 1 d . . . C18 C 0.3597(4) 0.4340(3) 1.0811(2) 0.0259(6) Uani 1 1 d . . . C19 C 0.2687(4) 0.5476(3) 1.0659(3) 0.0311(7) Uani 1 1 d . . . H19A H 0.1641 0.5376 1.0939 0.047 Uiso 1 1 calc R . . H19B H 0.2326 0.5585 0.9824 0.047 Uiso 1 1 calc R . . H19C H 0.3492 0.6221 1.1113 0.047 Uiso 1 1 calc R . . H3 H -0.145(3) -0.045(3) 0.655(2) 0.011(7) Uiso 1 1 d . . . H11 H 0.323(4) 0.404(3) 0.695(3) 0.020(7) Uiso 1 1 d . . . H9 H -0.066(4) 0.199(3) 0.441(3) 0.023(8) Uiso 1 1 d . . . H5 H -0.190(4) 0.324(3) 0.666(2) 0.018(7) Uiso 1 1 d . . . H17 H 0.327(4) 0.050(3) 0.829(3) 0.034(9) Uiso 1 1 d . . . Cl1 Cl 0.799(2) 0.1152(16) 0.9425(15) 0.054(4) Uiso 0.06 1 d PD A 1 C20 C 0.985(6) 0.059(4) 1.032(3) 0.061(18) Uiso 0.06 1 d PD . 1 H20A H 1.0904 0.1232 1.0493 0.073 Uiso 0.06 1 calc PR . 1 H20B H 0.9646 0.0421 1.1074 0.073 Uiso 0.06 1 calc PR . 1 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0156(10) 0.0288(11) 0.0386(12) -0.0056(9) 0.0100(9) -0.0064(8) O2 0.0325(12) 0.0272(11) 0.0336(12) 0.0107(9) 0.0111(10) 0.0009(9) O3 0.0429(14) 0.0353(13) 0.0248(12) -0.0004(10) -0.0093(10) -0.0089(10) S1 0.0135(3) 0.0211(4) 0.0341(4) 0.0017(3) 0.0078(3) 0.0014(3) S2 0.0164(3) 0.0185(3) 0.0263(4) -0.0018(3) 0.0069(3) -0.0036(3) S3 0.0252(4) 0.0323(4) 0.0234(4) 0.0036(3) -0.0048(3) 0.0006(3) C1 0.0137(13) 0.0193(13) 0.0208(14) 0.0006(11) 0.0041(11) 0.0031(10) C2 0.0117(12) 0.0198(13) 0.0143(13) 0.0006(10) 0.0005(10) -0.0011(10) C3 0.0165(13) 0.0182(14) 0.0169(14) 0.0020(11) 0.0028(11) 0.0007(11) C4 0.0174(13) 0.0167(13) 0.0204(14) 0.0000(11) 0.0046(11) -0.0003(10) C5 0.0137(13) 0.0195(14) 0.0265(16) 0.0017(11) 0.0058(11) -0.0017(11) C6 0.0207(14) 0.0217(14) 0.0195(15) -0.0035(11) 0.0057(11) -0.0057(11) C7 0.0313(17) 0.0213(15) 0.0440(19) 0.0008(13) 0.0150(15) -0.0026(12) C8 0.0104(12) 0.0195(13) 0.0209(14) -0.0003(11) 0.0063(10) 0.0029(10) C9 0.0110(12) 0.0192(13) 0.0228(15) -0.0017(11) 0.0054(11) -0.0001(11) C10 0.0114(12) 0.0173(13) 0.0243(15) -0.0004(11) 0.0050(11) 0.0008(10) C11 0.0137(13) 0.0237(14) 0.0225(15) -0.0030(12) 0.0030(12) 0.0007(11) C12 0.0155(13) 0.0254(15) 0.0264(16) 0.0063(12) 0.0051(11) 0.0034(11) C13 0.039(2) 0.054(2) 0.0264(18) 0.0159(16) -0.0085(14) -0.0179(16) C14 0.0086(12) 0.0256(14) 0.0198(14) 0.0036(11) 0.0022(10) -0.0008(10) C15 0.0140(13) 0.0261(14) 0.0208(14) 0.0022(11) 0.0049(11) -0.0022(11) C16 0.0183(13) 0.0244(14) 0.0207(15) 0.0049(11) 0.0036(11) -0.0026(11) C17 0.0184(14) 0.0280(16) 0.0241(16) 0.0001(12) 0.0030(12) -0.0003(12) C18 0.0250(15) 0.0298(16) 0.0189(15) 0.0019(12) 0.0052(12) -0.0111(12) C19 0.0337(17) 0.0323(17) 0.0240(16) -0.0046(13) 0.0091(13) -0.0044(13) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C6 1.221(3) . ? O2 C12 1.219(3) . ? O3 C18 1.221(3) . ? S1 C5 1.703(3) . ? S1 C4 1.716(3) . ? S2 C11 1.703(3) . ? S2 C10 1.723(3) . ? S3 C17 1.708(3) . ? S3 C16 1.727(3) . ? C1 C14 1.510(4) . ? C1 C8 1.516(4) . ? C1 C2 1.525(3) . ? C1 H1 1.0000 . ? C2 C5 1.357(4) . ? C2 C3 1.411(4) . ? C3 C4 1.372(4) . ? C3 H3 0.85(3) . ? C4 C6 1.459(4) . ? C5 H5 0.95(3) . ? C6 C7 1.500(4) . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C8 C11 1.373(4) . ? C8 C9 1.412(4) . ? C9 C10 1.365(4) . ? C9 H9 0.88(3) . ? C10 C12 1.456(4) . ? C11 H11 0.91(3) . ? C12 C13 1.499(4) . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C14 C17 1.366(4) . ? C14 C15 1.416(4) . ? C15 C16 1.368(4) . ? C15 H15 0.9500 . ? C16 C18 1.467(4) . ? C17 H17 0.97(3) . ? C18 C19 1.480(4) . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? Cl1 C20 1.768(10) . ? C20 C20 1.48(2) 2_757 ? C20 H20A 0.9900 . ? C20 H20B 0.9900 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C5 S1 C4 91.48(13) . . ? C11 S2 C10 91.50(13) . . ? C17 S3 C16 91.25(14) . . ? C14 C1 C8 114.2(2) . . ? C14 C1 C2 109.9(2) . . ? C8 C1 C2 111.4(2) . . ? C14 C1 H1 107.0 . . ? C8 C1 H1 107.0 . . ? C2 C1 H1 107.0 . . ? C5 C2 C3 111.8(2) . . ? C5 C2 C1 124.7(2) . . ? C3 C2 C1 123.5(2) . . ? C4 C3 C2 112.9(2) . . ? C4 C3 H3 120.5(18) . . ? C2 C3 H3 126.5(18) . . ? C3 C4 C6 130.1(3) . . ? C3 C4 S1 111.0(2) . . ? C6 C4 S1 118.9(2) . . ? C2 C5 S1 112.8(2) . . ? C2 C5 H5 128.7(17) . . ? S1 C5 H5 118.4(17) . . ? O1 C6 C4 120.5(3) . . ? O1 C6 C7 121.4(2) . . ? C4 C6 C7 118.0(2) . . ? C6 C7 H7A 109.5 . . ? C6 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C6 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C11 C8 C9 110.9(2) . . ? C11 C8 C1 126.9(2) . . ? C9 C8 C1 122.1(2) . . ? C10 C9 C8 113.8(2) . . ? C10 C9 H9 124.3(19) . . ? C8 C9 H9 121.8(19) . . ? C9 C10 C12 129.4(2) . . ? C9 C10 S2 110.9(2) . . ? C12 C10 S2 119.68(19) . . ? C8 C11 S2 112.9(2) . . ? C8 C11 H11 126.3(18) . . ? S2 C11 H11 120.8(18) . . ? O2 C12 C10 121.2(2) . . ? O2 C12 C13 120.5(3) . . ? C10 C12 C13 118.2(2) . . ? C12 C13 H13A 109.5 . . ? C12 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C12 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C17 C14 C15 111.3(2) . . ? C17 C14 C1 123.0(2) . . ? C15 C14 C1 125.7(2) . . ? C16 C15 C14 113.4(3) . . ? C16 C15 H15 123.3 . . ? C14 C15 H15 123.3 . . ? C15 C16 C18 129.8(3) . . ? C15 C16 S3 111.1(2) . . ? C18 C16 S3 119.0(2) . . ? C14 C17 S3 113.0(2) . . ? C14 C17 H17 126.5(19) . . ? S3 C17 H17 120.5(19) . . ? O3 C18 C16 119.6(3) . . ? O3 C18 C19 121.8(3) . . ? C16 C18 C19 118.6(2) . . ? C18 C19 H19A 109.5 . . ? C18 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C18 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C20 C20 Cl1 109(2) 2_757 . ? C20 C20 H20A 110.0 2_757 . ? Cl1 C20 H20A 110.0 . . ? C20 C20 H20B 110.0 2_757 . ? Cl1 C20 H20B 110.0 . . ? H20A C20 H20B 108.4 . . ? 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 C14 C1 C2 C5 84.3(3) . . . . ? C8 C1 C2 C5 -43.3(3) . . . . ? C14 C1 C2 C3 -93.8(3) . . . . ? C8 C1 C2 C3 138.6(3) . . . . ? C5 C2 C3 C4 -0.7(3) . . . . ? C1 C2 C3 C4 177.7(2) . . . . ? C2 C3 C4 C6 179.6(3) . . . . ? C2 C3 C4 S1 0.3(3) . . . . ? C5 S1 C4 C3 0.2(2) . . . . ? C5 S1 C4 C6 -179.3(2) . . . . ? C3 C2 C5 S1 0.8(3) . . . . ? C1 C2 C5 S1 -177.5(2) . . . . ? C4 S1 C5 C2 -0.6(2) . . . . ? C3 C4 C6 O1 -179.5(3) . . . . ? S1 C4 C6 O1 -0.2(4) . . . . ? C3 C4 C6 C7 2.2(4) . . . . ? S1 C4 C6 C7 -178.4(2) . . . . ? C14 C1 C8 C11 7.8(4) . . . . ? C2 C1 C8 C11 133.0(3) . . . . ? C14 C1 C8 C9 -175.3(2) . . . . ? C2 C1 C8 C9 -50.1(3) . . . . ? C11 C8 C9 C10 0.3(3) . . . . ? C1 C8 C9 C10 -177.0(2) . . . . ? C8 C9 C10 C12 179.5(3) . . . . ? C8 C9 C10 S2 -0.6(3) . . . . ? C11 S2 C10 C9 0.5(2) . . . . ? C11 S2 C10 C12 -179.5(2) . . . . ? C9 C8 C11 S2 0.1(3) . . . . ? C1 C8 C11 S2 177.2(2) . . . . ? C10 S2 C11 C8 -0.3(2) . . . . ? C9 C10 C12 O2 176.9(3) . . . . ? S2 C10 C12 O2 -3.1(4) . . . . ? C9 C10 C12 C13 -3.1(4) . . . . ? S2 C10 C12 C13 176.9(2) . . . . ? C8 C1 C14 C17 -125.9(3) . . . . ? C2 C1 C14 C17 108.1(3) . . . . ? C8 C1 C14 C15 55.0(3) . . . . ? C2 C1 C14 C15 -71.0(3) . . . . ? C17 C14 C15 C16 0.4(3) . . . . ? C1 C14 C15 C16 179.6(2) . . . . ? C14 C15 C16 C18 174.7(3) . . . . ? C14 C15 C16 S3 -0.7(3) . . . . ? C17 S3 C16 C15 0.6(2) . . . . ? C17 S3 C16 C18 -175.3(2) . . . . ? C15 C14 C17 S3 0.0(3) . . . . ? C1 C14 C17 S3 -179.2(2) . . . . ? C16 S3 C17 C14 -0.4(2) . . . . ? C15 C16 C18 O3 -171.8(3) . . . . ? S3 C16 C18 O3 3.3(4) . . . . ? C15 C16 C18 C19 7.2(4) . . . . ? S3 C16 C18 C19 -177.8(2) . . . . ? H1 C1 C2 C5 -159.9 . . . . ? H1 C1 C8 C11 -110.4 . . . . ? H1 C1 C14 C17 -7.7 . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 26.37 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.469 _refine_diff_density_min -0.303 _refine_diff_density_rms 0.071 # Attachment 'compounds_1-1e.cif' data_1 _database_code_depnum_ccdc_archive 'CCDC 677790' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '2(C19H16O3S3) 1.0(C3H6O1)' _chemical_formula_sum 'C41 H38 O7 S6' _chemical_formula_weight 835.07 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 8.1097(8) _cell_length_b 10.5562(10) _cell_length_c 12.3382(12) _cell_angle_alpha 94.864(2) _cell_angle_beta 107.949(2) _cell_angle_gamma 95.909(2) _cell_volume 991.89(17) _cell_formula_units_Z 1 _cell_measurement_temperature 125(2) _cell_measurement_reflns_used 6448 _cell_measurement_theta_min 1.75 _cell_measurement_theta_max 28.30 _exptl_crystal_description block _exptl_crystal_colour 'pale yellow' _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.398 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 436 _exptl_absorpt_coefficient_mu 0.395 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8908 _exptl_absorpt_correction_T_max 0.9805 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 125(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 'Bruker SMART 1000 CCD' _diffrn_measurement_method '/w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12473 _diffrn_reflns_av_R_equivalents 0.0233 _diffrn_reflns_av_sigmaI/netI 0.0346 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.75 _diffrn_reflns_theta_max 29.58 _reflns_number_total 5501 _reflns_number_gt 4247 _reflns_threshold_expression >2sigma(I) _computing_data_collection SMART _computing_cell_refinement 'SAINT (Bruker 2001)' _computing_data_reduction 'SAINT (Bruker 2001)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _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^)+(0.0495P)^2^+0.3464P] 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 5501 _refine_ls_number_parameters 291 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0550 _refine_ls_R_factor_gt 0.0370 _refine_ls_wR_factor_ref 0.0996 _refine_ls_wR_factor_gt 0.0898 _refine_ls_goodness_of_fit_ref 1.017 _refine_ls_restrained_S_all 1.017 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.25383(5) 0.54145(4) 0.48839(3) 0.02341(10) Uani 1 1 d . . . S2 S 0.90941(5) 0.82727(4) 0.34053(4) 0.02501(10) Uani 1 1 d . . . S3 S 0.06887(6) 0.80691(5) 0.00764(4) 0.03496(12) Uani 1 1 d . . . O1 O 0.44032(17) 0.53610(12) 0.73785(11) 0.0333(3) Uani 1 1 d . . . O2 O 1.13927(15) 1.06694(12) 0.35668(11) 0.0319(3) Uani 1 1 d . . . O3 O 0.0214(2) 0.58023(15) -0.16190(11) 0.0496(4) Uani 1 1 d . . . C1 C 0.40661(19) 0.82954(15) 0.32859(13) 0.0209(3) Uani 1 1 d . . . H1 H 0.3728 0.9112 0.3573 0.025 Uiso 1 1 calc R . . C2 C 0.37773(19) 0.73042(14) 0.40532(13) 0.0201(3) Uani 1 1 d . . . C3 C 0.48005(19) 0.74057(14) 0.52271(13) 0.0196(3) Uani 1 1 d . . . C4 C 0.42833(19) 0.64590(14) 0.57918(13) 0.0205(3) Uani 1 1 d . . . C5 C 0.2509(2) 0.62598(15) 0.37564(13) 0.0229(3) Uani 1 1 d . . . C6 C 0.5015(2) 0.62569(16) 0.69980(14) 0.0249(3) Uani 1 1 d . . . C7 C 0.6549(3) 0.7181(2) 0.77415(16) 0.0431(5) Uani 1 1 d . . . H7A H 0.6618 0.7171 0.8548 0.065 Uiso 1 1 calc R . . H7B H 0.6410 0.8047 0.7529 0.065 Uiso 1 1 calc R . . H7C H 0.7625 0.6931 0.7635 0.065 Uiso 1 1 calc R . . C8 C 0.59831(19) 0.85689(14) 0.33783(12) 0.0196(3) Uani 1 1 d . . . C9 C 0.6883(2) 0.98206(15) 0.34715(13) 0.0210(3) Uani 1 1 d . . . C10 C 0.8587(2) 0.98126(14) 0.34949(13) 0.0209(3) Uani 1 1 d . . . C11 C 0.7035(2) 0.76495(15) 0.33395(14) 0.0230(3) Uani 1 1 d . . . C12 C 0.9934(2) 1.08796(15) 0.35594(14) 0.0250(3) Uani 1 1 d . . . C13 C 0.9456(2) 1.22073(16) 0.35863(17) 0.0347(4) Uani 1 1 d . . . H13A H 1.0522 1.2830 0.3827 0.052 Uiso 1 1 calc R . . H13B H 0.8807 1.2326 0.4131 0.052 Uiso 1 1 calc R . . H13C H 0.8724 1.2338 0.2819 0.052 Uiso 1 1 calc R . . C14 C 0.29355(19) 0.79496(15) 0.20422(13) 0.0228(3) Uani 1 1 d . . . C15 C 0.2970(2) 0.68323(17) 0.13230(13) 0.0248(3) Uani 1 1 d . . . C16 C 0.1813(2) 0.67580(16) 0.02338(14) 0.0274(3) Uani 1 1 d . . . C17 C 0.1766(2) 0.86964(18) 0.14705(15) 0.0285(4) Uani 1 1 d . . . C18 C 0.1403(2) 0.57430(18) -0.07401(14) 0.0330(4) Uani 1 1 d . . . C19 C 0.2453(3) 0.4661(2) -0.06312(16) 0.0397(5) Uani 1 1 d . . . H19A H 0.1716 0.3881 -0.1081 0.060 Uiso 1 1 calc R . . H19B H 0.2900 0.4524 0.0177 0.060 Uiso 1 1 calc R . . H19C H 0.3437 0.4864 -0.0919 0.060 Uiso 1 1 calc R . . H3 H 0.573(2) 0.8033(17) 0.5542(15) 0.020(4) Uiso 1 1 d . . . H5 H 0.167(3) 0.598(2) 0.3047(17) 0.035(5) Uiso 1 1 d . . . H9 H 0.639(2) 1.0534(17) 0.3524(14) 0.014(4) Uiso 1 1 d . . . H11 H 0.674(2) 0.6737(18) 0.3330(15) 0.026(5) Uiso 1 1 d . . . H15 H 0.364(2) 0.6199(17) 0.1539(15) 0.018(4) Uiso 1 1 d . . . H17 H 0.147(3) 0.9441(19) 0.1763(16) 0.029(5) Uiso 1 1 d . . . O50 O 0.3951(5) -0.1527(3) 0.8716(3) 0.0577(9) Uani 0.50 1 d P A -1 C50 C 0.4739(6) -0.0745(4) 0.9525(3) 0.0390(9) Uani 0.50 1 d P A -1 C51 C 0.4195(9) 0.0554(6) 0.9662(6) 0.0495(14) Uani 0.50 1 d P A -1 H51A H 0.5178 0.1214 0.9733 0.074 Uiso 0.50 1 calc PR A -1 H51B H 0.3843 0.0653 1.0353 0.074 Uiso 0.50 1 calc PR A -1 H51C H 0.3208 0.0646 0.8988 0.074 Uiso 0.50 1 calc PR A -1 C52 C 0.6288(8) -0.1056(7) 1.0457(5) 0.0514(15) Uani 0.50 1 d P A -1 H52A H 0.6587 -0.1891 1.0227 0.077 Uiso 0.50 1 calc PR A -1 H52B H 0.5998 -0.1086 1.1170 0.077 Uiso 0.50 1 calc PR A -1 H52C H 0.7289 -0.0393 1.0581 0.077 Uiso 0.50 1 calc PR A -1 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 0.02200(19) 0.01960(18) 0.0259(2) -0.00182(14) 0.00735(15) -0.00478(14) S2 0.01907(18) 0.02139(19) 0.0341(2) 0.00173(16) 0.00883(16) 0.00109(14) S3 0.0297(2) 0.0378(3) 0.0268(2) 0.00746(18) -0.00509(17) -0.00179(18) O1 0.0404(7) 0.0281(6) 0.0310(6) 0.0079(5) 0.0118(5) -0.0024(5) O2 0.0229(6) 0.0305(6) 0.0396(7) -0.0034(5) 0.0112(5) -0.0054(5) O3 0.0549(9) 0.0464(8) 0.0269(7) 0.0007(6) -0.0096(6) -0.0112(7) C1 0.0167(7) 0.0221(7) 0.0212(7) 0.0015(6) 0.0030(5) 0.0004(5) C2 0.0164(7) 0.0212(7) 0.0211(7) -0.0003(6) 0.0051(5) 0.0013(5) C3 0.0159(6) 0.0186(7) 0.0221(7) -0.0011(6) 0.0048(6) -0.0004(5) C4 0.0180(7) 0.0194(7) 0.0222(7) -0.0009(6) 0.0056(6) -0.0003(5) C5 0.0195(7) 0.0246(8) 0.0209(7) -0.0012(6) 0.0040(6) -0.0024(6) C6 0.0250(8) 0.0251(8) 0.0237(8) 0.0032(6) 0.0069(6) 0.0009(6) C7 0.0392(11) 0.0518(12) 0.0256(9) 0.0088(8) -0.0018(8) -0.0166(9) C8 0.0175(7) 0.0212(7) 0.0176(7) 0.0003(5) 0.0035(5) -0.0003(5) C9 0.0207(7) 0.0191(7) 0.0203(7) -0.0003(6) 0.0042(6) -0.0006(6) C10 0.0206(7) 0.0186(7) 0.0211(7) 0.0002(6) 0.0051(6) -0.0007(6) C11 0.0198(7) 0.0201(7) 0.0274(8) 0.0021(6) 0.0068(6) -0.0020(6) C12 0.0232(7) 0.0239(8) 0.0238(7) -0.0020(6) 0.0056(6) -0.0048(6) C13 0.0347(9) 0.0216(8) 0.0460(11) 0.0012(7) 0.0135(8) -0.0039(7) C14 0.0166(7) 0.0284(8) 0.0210(7) 0.0030(6) 0.0044(6) -0.0028(6) C15 0.0211(7) 0.0291(8) 0.0216(7) 0.0031(6) 0.0047(6) -0.0026(6) C16 0.0237(8) 0.0308(8) 0.0231(8) 0.0046(6) 0.0041(6) -0.0067(6) C17 0.0239(8) 0.0312(9) 0.0254(8) 0.0050(7) 0.0015(6) 0.0000(7) C18 0.0338(9) 0.0369(10) 0.0218(8) 0.0020(7) 0.0063(7) -0.0147(7) C19 0.0408(11) 0.0459(11) 0.0284(9) -0.0062(8) 0.0114(8) -0.0045(9) O50 0.058(2) 0.055(2) 0.0452(18) -0.0060(15) -0.0010(15) 0.0050(16) C50 0.044(2) 0.046(2) 0.0278(19) 0.0050(17) 0.0144(17) -0.0012(18) C51 0.053(4) 0.051(4) 0.049(3) 0.007(3) 0.023(3) 0.003(2) C52 0.048(3) 0.072(5) 0.028(2) 0.010(3) 0.004(2) 0.003(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 S1 C5 1.7107(17) . ? S1 C4 1.7220(15) . ? S2 C11 1.7052(16) . ? S2 C10 1.7203(16) . ? S3 C17 1.7093(17) . ? S3 C16 1.7266(19) . ? O1 C6 1.218(2) . ? O2 C12 1.224(2) . ? O3 C18 1.221(2) . ? C1 C14 1.516(2) . ? C1 C2 1.517(2) . ? C1 C8 1.519(2) . ? C1 H1 1.0000 . ? C2 C5 1.369(2) . ? C2 C3 1.419(2) . ? C3 C4 1.368(2) . ? C3 H3 0.910(19) . ? C4 C6 1.466(2) . ? C5 H5 0.93(2) . ? C6 C7 1.496(2) . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C8 C11 1.364(2) . ? C8 C9 1.420(2) . ? C9 C10 1.374(2) . ? C9 H9 0.894(17) . ? C10 C12 1.465(2) . ? C11 H11 0.966(19) . ? C12 C13 1.492(2) . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C14 C17 1.362(2) . ? C14 C15 1.423(2) . ? C15 C16 1.372(2) . ? C15 H15 0.912(18) . ? C16 C18 1.471(2) . ? C17 H17 0.92(2) . ? C18 C19 1.485(3) . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? O50 C50 1.202(5) . ? C50 C51 1.495(7) . ? C50 C52 1.505(7) . ? C51 H51A 0.9800 . ? C51 H51B 0.9800 . ? C51 H51C 0.9800 . ? C52 H52A 0.9800 . ? C52 H52B 0.9800 . ? C52 H52C 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 C5 S1 C4 91.47(8) . . ? C11 S2 C10 91.48(8) . . ? C17 S3 C16 91.32(8) . . ? C14 C1 C2 113.42(12) . . ? C14 C1 C8 110.65(13) . . ? C2 C1 C8 111.45(12) . . ? C14 C1 H1 107.0 . . ? C2 C1 H1 107.0 . . ? C8 C1 H1 107.0 . . ? C5 C2 C3 111.29(14) . . ? C5 C2 C1 126.68(14) . . ? C3 C2 C1 121.96(13) . . ? C4 C3 C2 113.35(13) . . ? C4 C3 H3 125.2(11) . . ? C2 C3 H3 121.4(11) . . ? C3 C4 C6 128.81(14) . . ? C3 C4 S1 111.17(11) . . ? C6 C4 S1 120.02(12) . . ? C2 C5 S1 112.71(12) . . ? C2 C5 H5 128.6(13) . . ? S1 C5 H5 118.7(13) . . ? O1 C6 C4 121.12(15) . . ? O1 C6 C7 121.20(15) . . ? C4 C6 C7 117.68(15) . . ? C6 C7 H7A 109.5 . . ? C6 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C6 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C11 C8 C9 111.61(14) . . ? C11 C8 C1 124.55(14) . . ? C9 C8 C1 123.80(14) . . ? C10 C9 C8 112.74(14) . . ? C10 C9 H9 124.1(11) . . ? C8 C9 H9 123.2(11) . . ? C9 C10 C12 130.10(15) . . ? C9 C10 S2 111.29(11) . . ? C12 C10 S2 118.61(12) . . ? C8 C11 S2 112.87(12) . . ? C8 C11 H11 126.7(11) . . ? S2 C11 H11 120.3(11) . . ? O2 C12 C10 120.12(15) . . ? O2 C12 C13 121.72(15) . . ? C10 C12 C13 118.14(15) . . ? C12 C13 H13A 109.5 . . ? C12 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C12 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C17 C14 C15 111.57(14) . . ? C17 C14 C1 123.39(15) . . ? C15 C14 C1 125.04(14) . . ? C16 C15 C14 112.92(16) . . ? C16 C15 H15 121.3(11) . . ? C14 C15 H15 125.8(11) . . ? C15 C16 C18 129.71(17) . . ? C15 C16 S3 111.20(13) . . ? C18 C16 S3 119.06(13) . . ? C14 C17 S3 112.98(14) . . ? C14 C17 H17 127.5(12) . . ? S3 C17 H17 119.4(12) . . ? O3 C18 C16 119.78(19) . . ? O3 C18 C19 121.21(17) . . ? C16 C18 C19 119.01(16) . . ? C18 C19 H19A 109.5 . . ? C18 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C18 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? O50 C50 C51 121.5(5) . . ? O50 C50 C52 120.9(5) . . ? C51 C50 C52 117.5(5) . . ? 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 C14 C1 C2 C5 -7.8(2) . . . . ? C8 C1 C2 C5 -133.46(16) . . . . ? C14 C1 C2 C3 175.29(14) . . . . ? C8 C1 C2 C3 49.62(19) . . . . ? C5 C2 C3 C4 -0.7(2) . . . . ? C1 C2 C3 C4 176.68(14) . . . . ? C2 C3 C4 C6 -179.70(15) . . . . ? C2 C3 C4 S1 0.60(17) . . . . ? C5 S1 C4 C3 -0.30(13) . . . . ? C5 S1 C4 C6 179.97(14) . . . . ? C3 C2 C5 S1 0.43(18) . . . . ? C1 C2 C5 S1 -176.76(12) . . . . ? C4 S1 C5 C2 -0.09(13) . . . . ? C3 C4 C6 O1 179.90(16) . . . . ? S1 C4 C6 O1 -0.4(2) . . . . ? C3 C4 C6 C7 -0.7(3) . . . . ? S1 C4 C6 C7 178.97(14) . . . . ? C14 C1 C8 C11 -80.56(19) . . . . ? C2 C1 C8 C11 46.6(2) . . . . ? C14 C1 C8 C9 96.88(17) . . . . ? C2 C1 C8 C9 -135.93(15) . . . . ? C11 C8 C9 C10 0.30(19) . . . . ? C1 C8 C9 C10 -177.43(14) . . . . ? C8 C9 C10 C12 178.61(15) . . . . ? C8 C9 C10 S2 -0.11(17) . . . . ? C11 S2 C10 C9 -0.08(12) . . . . ? C11 S2 C10 C12 -178.96(13) . . . . ? C9 C8 C11 S2 -0.36(17) . . . . ? C1 C8 C11 S2 177.35(12) . . . . ? C10 S2 C11 C8 0.26(13) . . . . ? C9 C10 C12 O2 -179.75(16) . . . . ? S2 C10 C12 O2 -1.1(2) . . . . ? C9 C10 C12 C13 -1.2(3) . . . . ? S2 C10 C12 C13 177.43(13) . . . . ? C2 C1 C14 C17 120.45(17) . . . . ? C8 C1 C14 C17 -113.46(17) . . . . ? C2 C1 C14 C15 -60.5(2) . . . . ? C8 C1 C14 C15 65.59(19) . . . . ? C17 C14 C15 C16 -0.7(2) . . . . ? C1 C14 C15 C16 -179.85(14) . . . . ? C14 C15 C16 C18 -177.26(16) . . . . ? C14 C15 C16 S3 0.68(18) . . . . ? C17 S3 C16 C15 -0.38(13) . . . . ? C17 S3 C16 C18 177.80(14) . . . . ? C15 C14 C17 S3 0.40(19) . . . . ? C1 C14 C17 S3 179.56(12) . . . . ? C16 S3 C17 C14 -0.02(14) . . . . ? C15 C16 C18 O3 173.63(18) . . . . ? S3 C16 C18 O3 -4.2(2) . . . . ? C15 C16 C18 C19 -6.4(3) . . . . ? S3 C16 C18 C19 175.85(13) . . . . ? H1 C1 C2 C5 109.9 . . . . ? H1 C1 C8 C11 163.2 . . . . ? H1 C1 C14 C17 2.7 . . . . ? _diffrn_measured_fraction_theta_max 0.986 _diffrn_reflns_theta_full 29.58 _diffrn_measured_fraction_theta_full 0.986 _refine_diff_density_max 0.496 _refine_diff_density_min -0.242 _refine_diff_density_rms 0.059 data_1a _database_code_depnum_ccdc_archive 'CCDC 677791' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '2(C19H16O3S3) 0.84(C3H6O1)' _chemical_formula_sum 'C40.52 H37.04 O6.84 S6' _chemical_formula_weight 825.78 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 8.0970(12) _cell_length_b 10.5845(15) _cell_length_c 12.3055(18) _cell_angle_alpha 95.020(3) _cell_angle_beta 107.818(2) _cell_angle_gamma 95.907(2) _cell_volume 990.8(2) _cell_formula_units_Z 1 _cell_measurement_temperature 125(2) _cell_measurement_reflns_used 2854 _cell_measurement_theta_min 1.75 _cell_measurement_theta_max 26.44 _exptl_crystal_description block _exptl_crystal_colour 'pale yellow' _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.384 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 431 _exptl_absorpt_coefficient_mu 0.394 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8843 _exptl_absorpt_correction_T_max 0.9396 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 125(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 'Bruker SMART 1000 CCD' _diffrn_measurement_method '/w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11973 _diffrn_reflns_av_R_equivalents 0.0270 _diffrn_reflns_av_sigmaI/netI 0.0348 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.75 _diffrn_reflns_theta_max 29.61 _reflns_number_total 5448 _reflns_number_gt 4531 _reflns_threshold_expression >2sigma(I) _computing_data_collection SMART _computing_cell_refinement 'SAINT (Bruker 2001)' _computing_data_reduction 'SAINT (Bruker 2001)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _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^)+(0.0753P)^2^+1.0423P] 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 5448 _refine_ls_number_parameters 268 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0640 _refine_ls_R_factor_gt 0.0529 _refine_ls_wR_factor_ref 0.1506 _refine_ls_wR_factor_gt 0.1421 _refine_ls_goodness_of_fit_ref 1.050 _refine_ls_restrained_S_all 1.051 _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 O1 O -0.6402(2) -0.06685(17) 0.14376(16) 0.0343(4) Uani 1 1 d . . . O2 O 0.0589(2) 0.46446(17) -0.23858(16) 0.0356(4) Uani 1 1 d . . . O3 O 0.4774(3) 0.4207(2) 0.66333(17) 0.0522(6) Uani 1 1 d . . . S1 S -0.41044(7) 0.17225(5) 0.15929(5) 0.02713(14) Uani 1 1 d . . . S2 S 0.24617(7) 0.45873(5) 0.01120(5) 0.02550(14) Uani 1 1 d . . . S3 S 0.42884(8) 0.19350(7) 0.49299(5) 0.03727(17) Uani 1 1 d . . . C1 C 0.0936(3) 0.1710(2) 0.17077(18) 0.0222(4) Uani 1 1 d . . . H1 H 0.1279 0.0898 0.1418 0.027 Uiso 1 1 calc R . . C2 C -0.0981(3) 0.1432(2) 0.16189(17) 0.0216(4) Uani 1 1 d . . . C3 C -0.1874(3) 0.0181(2) 0.15316(18) 0.0232(4) Uani 1 1 d . . . H3 H -0.1353 -0.0578 0.1493 0.028 Uiso 1 1 calc R . . C4 C -0.3588(3) 0.0195(2) 0.15093(18) 0.0229(4) Uani 1 1 d . . . C5 C -0.2048(3) 0.2351(2) 0.16545(19) 0.0253(4) Uani 1 1 d . . . H5 H -0.1680 0.3242 0.1708 0.030 Uiso 1 1 calc R . . C6 C -0.4927(3) -0.0874(2) 0.14472(19) 0.0266(4) Uani 1 1 d . . . C7 C -0.4451(3) -0.2201(2) 0.1421(3) 0.0370(5) Uani 1 1 d . . . H7A H -0.3684 -0.2318 0.2183 0.055 Uiso 1 1 calc R . . H7B H -0.3840 -0.2333 0.0853 0.055 Uiso 1 1 calc R . . H7C H -0.5517 -0.2822 0.1209 0.055 Uiso 1 1 calc R . . C8 C 0.1226(2) 0.2701(2) 0.09459(18) 0.0214(4) Uani 1 1 d . . . C9 C 0.0197(3) 0.2595(2) -0.02294(18) 0.0218(4) Uani 1 1 d . . . H9 H -0.0754 0.1935 -0.0588 0.026 Uiso 1 1 calc R . . C10 C 0.0715(3) 0.3544(2) -0.07945(18) 0.0226(4) Uani 1 1 d . . . C11 C 0.2500(3) 0.3744(2) 0.12420(18) 0.0248(4) Uani 1 1 d . . . H11 H 0.3314 0.3974 0.1993 0.030 Uiso 1 1 calc R . . C12 C -0.0014(3) 0.3743(2) -0.2006(2) 0.0279(4) Uani 1 1 d . . . C13 C -0.1545(4) 0.2813(3) -0.2754(2) 0.0466(7) Uani 1 1 d . . . H13A H -0.2626 0.3056 -0.2646 0.070 Uiso 1 1 calc R . . H13B H -0.1399 0.1950 -0.2543 0.070 Uiso 1 1 calc R . . H13C H -0.1613 0.2825 -0.3562 0.070 Uiso 1 1 calc R . . C14 C 0.2065(3) 0.2061(2) 0.29585(18) 0.0249(4) Uani 1 1 d . . . C15 C 0.2034(3) 0.3181(2) 0.36784(19) 0.0268(4) Uani 1 1 d . . . H15 H 0.1302 0.3815 0.3428 0.032 Uiso 1 1 calc R . . C16 C 0.3175(3) 0.3245(2) 0.4773(2) 0.0302(5) Uani 1 1 d . . . C17 C 0.3224(3) 0.1306(2) 0.3536(2) 0.0310(5) Uani 1 1 d . . . H17 H 0.3415 0.0516 0.3197 0.037 Uiso 1 1 calc R . . C18 C 0.3600(3) 0.4265(3) 0.5750(2) 0.0349(5) Uani 1 1 d . . . C19 C 0.2562(4) 0.5358(3) 0.5638(2) 0.0421(6) Uani 1 1 d . . . H19A H 0.1607 0.5185 0.5960 0.063 Uiso 1 1 calc R . . H19B H 0.2073 0.5465 0.4823 0.063 Uiso 1 1 calc R . . H19C H 0.3323 0.6143 0.6056 0.063 Uiso 1 1 calc R . . O4 O 0.1036(8) 1.1530(6) 0.6298(5) 0.0550(14) Uani 0.42 1 d P A -1 C20 C 0.0267(8) 1.0748(6) 0.5483(5) 0.0370(13) Uani 0.42 1 d PD A -1 C21 C 0.0801(13) 0.9427(7) 0.5325(8) 0.0472(19) Uani 0.42 1 d PD A -1 H21A H 0.1576 0.9441 0.4850 0.071 Uiso 0.42 1 calc PR A -1 H21B H -0.0247 0.8804 0.4945 0.071 Uiso 0.42 1 calc PR A -1 H21C H 0.1416 0.9182 0.6079 0.071 Uiso 0.42 1 calc PR A -1 C22 C -0.1316(12) 1.1058(11) 0.4544(7) 0.052(2) Uani 0.42 1 d PD A -1 H22A H -0.1862 1.1714 0.4868 0.078 Uiso 0.42 1 calc PR A -1 H22B H -0.2166 1.0282 0.4239 0.078 Uiso 0.42 1 calc PR A -1 H22C H -0.0937 1.1376 0.3922 0.078 Uiso 0.42 1 calc PR A -1 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0210(7) 0.0355(9) 0.0429(10) -0.0042(7) 0.0106(7) -0.0056(6) O2 0.0378(9) 0.0336(9) 0.0348(9) 0.0094(7) 0.0113(7) -0.0018(7) O3 0.0559(13) 0.0496(12) 0.0306(10) 0.0010(8) -0.0091(9) -0.0106(10) S1 0.0191(2) 0.0252(3) 0.0370(3) 0.0025(2) 0.0096(2) 0.00188(18) S2 0.0208(2) 0.0235(3) 0.0295(3) -0.00148(19) 0.0078(2) -0.00434(18) S3 0.0297(3) 0.0417(3) 0.0300(3) 0.0085(2) -0.0050(2) -0.0008(2) C1 0.0155(8) 0.0260(10) 0.0220(9) 0.0018(7) 0.0023(7) 0.0004(7) C2 0.0172(8) 0.0235(9) 0.0205(9) 0.0004(7) 0.0027(7) -0.0016(7) C3 0.0194(9) 0.0247(10) 0.0228(9) 0.0007(7) 0.0047(7) -0.0008(7) C4 0.0192(9) 0.0205(9) 0.0261(10) -0.0016(7) 0.0056(7) -0.0015(7) C5 0.0202(9) 0.0242(10) 0.0297(10) 0.0024(8) 0.0068(8) -0.0006(7) C6 0.0217(9) 0.0269(10) 0.0277(10) -0.0022(8) 0.0067(8) -0.0047(8) C7 0.0327(12) 0.0248(11) 0.0520(15) 0.0024(10) 0.0143(11) -0.0028(9) C8 0.0148(8) 0.0242(9) 0.0235(9) 0.0004(7) 0.0051(7) 0.0000(7) C9 0.0154(8) 0.0237(9) 0.0238(9) -0.0007(7) 0.0045(7) -0.0001(7) C10 0.0169(8) 0.0228(9) 0.0259(10) -0.0004(7) 0.0055(7) -0.0001(7) C11 0.0186(9) 0.0273(10) 0.0239(9) -0.0019(8) 0.0033(7) -0.0026(7) C12 0.0243(10) 0.0289(11) 0.0293(11) 0.0038(8) 0.0077(8) 0.0003(8) C13 0.0386(14) 0.0582(18) 0.0286(12) 0.0118(12) -0.0038(10) -0.0191(13) C14 0.0178(9) 0.0313(11) 0.0227(9) 0.0037(8) 0.0039(7) -0.0014(8) C15 0.0196(9) 0.0344(11) 0.0233(10) 0.0026(8) 0.0045(8) -0.0017(8) C16 0.0235(10) 0.0367(12) 0.0255(10) 0.0035(9) 0.0044(8) -0.0063(9) C17 0.0225(10) 0.0336(12) 0.0300(11) 0.0039(9) -0.0001(8) -0.0012(8) C18 0.0317(11) 0.0413(13) 0.0247(10) 0.0027(9) 0.0052(9) -0.0135(10) C19 0.0412(14) 0.0499(16) 0.0324(13) -0.0052(11) 0.0131(11) -0.0023(12) O4 0.055(3) 0.055(3) 0.042(3) -0.007(2) 0.003(2) 0.002(3) C20 0.037(3) 0.049(4) 0.027(3) 0.003(2) 0.015(3) -0.001(3) C21 0.049(5) 0.052(5) 0.042(5) 0.004(4) 0.020(4) -0.002(4) C22 0.046(5) 0.079(7) 0.028(3) 0.016(4) 0.005(3) 0.006(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C6 1.233(3) . ? O2 C12 1.220(3) . ? O3 C18 1.217(3) . ? S1 C5 1.705(2) . ? S1 C4 1.713(2) . ? S2 C11 1.711(2) . ? S2 C10 1.721(2) . ? S3 C17 1.705(2) . ? S3 C16 1.724(3) . ? C1 C8 1.513(3) . ? C1 C2 1.517(3) . ? C1 C14 1.521(3) . ? C2 C5 1.372(3) . ? C2 C3 1.421(3) . ? C3 C4 1.381(3) . ? C4 C6 1.464(3) . ? C6 C7 1.494(3) . ? C8 C11 1.372(3) . ? C8 C9 1.419(3) . ? C9 C10 1.372(3) . ? C10 C12 1.468(3) . ? C12 C13 1.499(3) . ? C14 C17 1.367(3) . ? C14 C15 1.424(3) . ? C15 C16 1.372(3) . ? C16 C18 1.473(3) . ? C18 C19 1.490(4) . ? O4 C20 1.202(8) . ? C20 C21 1.519(8) . ? C20 C22 1.527(7) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C5 S1 C4 91.56(10) . . ? C11 S2 C10 91.49(10) . . ? C17 S3 C16 91.58(12) . . ? C8 C1 C2 111.66(16) . . ? C8 C1 C14 113.17(17) . . ? C2 C1 C14 110.43(17) . . ? C5 C2 C3 111.58(19) . . ? C5 C2 C1 124.56(19) . . ? C3 C2 C1 123.82(19) . . ? C4 C3 C2 112.30(19) . . ? C3 C4 C6 129.5(2) . . ? C3 C4 S1 111.74(16) . . ? C6 C4 S1 118.77(16) . . ? C2 C5 S1 112.81(16) . . ? O1 C6 C4 120.0(2) . . ? O1 C6 C7 121.3(2) . . ? C4 C6 C7 118.6(2) . . ? C11 C8 C9 111.42(19) . . ? C11 C8 C1 126.95(19) . . ? C9 C8 C1 121.56(18) . . ? C10 C9 C8 113.08(18) . . ? C9 C10 C12 128.77(19) . . ? C9 C10 S2 111.35(16) . . ? C12 C10 S2 119.88(16) . . ? C8 C11 S2 112.66(16) . . ? O2 C12 C10 121.2(2) . . ? O2 C12 C13 121.2(2) . . ? C10 C12 C13 117.6(2) . . ? C17 C14 C15 111.7(2) . . ? C17 C14 C1 123.2(2) . . ? C15 C14 C1 125.10(19) . . ? C16 C15 C14 112.7(2) . . ? C15 C16 C18 129.6(2) . . ? C15 C16 S3 111.33(19) . . ? C18 C16 S3 118.97(18) . . ? C14 C17 S3 112.75(19) . . ? O3 C18 C16 120.3(3) . . ? O3 C18 C19 120.8(3) . . ? C16 C18 C19 118.9(2) . . ? O4 C20 C21 122.8(7) . . ? O4 C20 C22 120.4(7) . . ? C21 C20 C22 116.8(8) . . ? 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 C8 C1 C2 C5 -46.0(3) . . . . ? C14 C1 C2 C5 80.9(3) . . . . ? C8 C1 C2 C3 136.5(2) . . . . ? C14 C1 C2 C3 -96.6(2) . . . . ? C5 C2 C3 C4 -0.3(3) . . . . ? C1 C2 C3 C4 177.53(19) . . . . ? C2 C3 C4 C6 -178.8(2) . . . . ? C2 C3 C4 S1 0.1(2) . . . . ? C5 S1 C4 C3 0.14(17) . . . . ? C5 S1 C4 C6 179.11(18) . . . . ? C3 C2 C5 S1 0.4(2) . . . . ? C1 C2 C5 S1 -177.41(16) . . . . ? C4 S1 C5 C2 -0.30(18) . . . . ? C3 C4 C6 O1 179.9(2) . . . . ? S1 C4 C6 O1 1.1(3) . . . . ? C3 C4 C6 C7 1.1(4) . . . . ? S1 C4 C6 C7 -177.64(18) . . . . ? C2 C1 C8 C11 133.7(2) . . . . ? C14 C1 C8 C11 8.4(3) . . . . ? C2 C1 C8 C9 -49.7(3) . . . . ? C14 C1 C8 C9 -175.00(19) . . . . ? C11 C8 C9 C10 0.5(3) . . . . ? C1 C8 C9 C10 -176.64(18) . . . . ? C8 C9 C10 C12 179.4(2) . . . . ? C8 C9 C10 S2 -0.5(2) . . . . ? C11 S2 C10 C9 0.33(17) . . . . ? C11 S2 C10 C12 -179.57(18) . . . . ? C9 C8 C11 S2 -0.2(2) . . . . ? C1 C8 C11 S2 176.70(17) . . . . ? C10 S2 C11 C8 -0.06(18) . . . . ? C9 C10 C12 O2 179.7(2) . . . . ? S2 C10 C12 O2 -0.5(3) . . . . ? C9 C10 C12 C13 0.7(4) . . . . ? S2 C10 C12 C13 -179.4(2) . . . . ? C8 C1 C14 C17 -121.6(2) . . . . ? C2 C1 C14 C17 112.4(2) . . . . ? C8 C1 C14 C15 59.9(3) . . . . ? C2 C1 C14 C15 -66.1(3) . . . . ? C17 C14 C15 C16 0.4(3) . . . . ? C1 C14 C15 C16 179.2(2) . . . . ? C14 C15 C16 C18 176.5(2) . . . . ? C14 C15 C16 S3 -0.1(3) . . . . ? C17 S3 C16 C15 -0.14(19) . . . . ? C17 S3 C16 C18 -177.22(19) . . . . ? C15 C14 C17 S3 -0.6(3) . . . . ? C1 C14 C17 S3 -179.30(16) . . . . ? C16 S3 C17 C14 0.40(19) . . . . ? C15 C16 C18 O3 -173.2(3) . . . . ? S3 C16 C18 O3 3.3(3) . . . . ? C15 C16 C18 C19 7.2(4) . . . . ? S3 C16 C18 C19 -176.30(19) . . . . ? H1 C1 C2 C5 -162.9 . . . . ? H1 C1 C8 C11 -109.4 . . . . ? H1 C1 C14 C17 -3.8 . . . . ? _diffrn_measured_fraction_theta_max 0.976 _diffrn_reflns_theta_full 29.61 _diffrn_measured_fraction_theta_full 0.976 _refine_diff_density_max 0.769 _refine_diff_density_min -0.557 _refine_diff_density_rms 0.086 data_1aA _database_code_depnum_ccdc_archive 'CCDC 677792' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '2(C19H16O3S3) 1.0(C3H6O1)' _chemical_formula_sum 'C41 H38 O7 S6' _chemical_formula_weight 835.07 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 8.1018(6) _cell_length_b 10.5888(8) _cell_length_c 12.3159(9) _cell_angle_alpha 94.9990(10) _cell_angle_beta 107.7650(10) _cell_angle_gamma 95.9600(10) _cell_volume 992.83(13) _cell_formula_units_Z 1 _cell_measurement_temperature 125(2) _cell_measurement_reflns_used 7827 _cell_measurement_theta_min 1.75 _cell_measurement_theta_max 28.43 _exptl_crystal_description block _exptl_crystal_colour 'pale yellow' _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.397 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 436 _exptl_absorpt_coefficient_mu 0.394 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8842 _exptl_absorpt_correction_T_max 0.9396 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 125(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 'Bruker SMART 1000 CCD' _diffrn_measurement_method '/w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12331 _diffrn_reflns_av_R_equivalents 0.0246 _diffrn_reflns_av_sigmaI/netI 0.0323 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.75 _diffrn_reflns_theta_max 29.61 _reflns_number_total 5473 _reflns_number_gt 4433 _reflns_threshold_expression >2sigma(I) _computing_data_collection SMART _computing_cell_refinement 'SAINT (Bruker 2001)' _computing_data_reduction 'SAINT (Bruker 2001)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _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^)+(0.0734P)^2^+0.3314P] 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 5473 _refine_ls_number_parameters 268 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0531 _refine_ls_R_factor_gt 0.0403 _refine_ls_wR_factor_ref 0.1214 _refine_ls_wR_factor_gt 0.1094 _refine_ls_goodness_of_fit_ref 1.020 _refine_ls_restrained_S_all 1.022 _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 O1 O 0.36055(16) 0.43273(12) 0.14375(11) 0.0324(3) Uani 1 1 d . . . O2 O 1.05948(18) 0.96469(12) -0.23781(11) 0.0340(3) Uani 1 1 d . . . O3 O 1.4766(2) 0.92002(16) 0.66279(12) 0.0509(4) Uani 1 1 d . . . S1 S 0.59044(5) 0.67218(4) 0.15947(4) 0.02589(11) Uani 1 1 d . . . S2 S 1.24693(5) 0.95879(4) 0.01145(3) 0.02412(11) Uani 1 1 d . . . S3 S 1.42966(6) 0.69374(5) 0.49257(4) 0.03553(13) Uani 1 1 d . . . C1 C 1.09414(19) 0.67087(15) 0.17093(13) 0.0215(3) Uani 1 1 d . . . H1 H 1.1284 0.5896 0.1420 0.026 Uiso 1 1 calc R . . C2 C 0.90214(19) 0.64315(15) 0.16188(13) 0.0205(3) Uani 1 1 d . . . C3 C 0.8124(2) 0.51800(15) 0.15251(13) 0.0224(3) Uani 1 1 d . . . H3 H 0.8645 0.4422 0.1481 0.027 Uiso 1 1 calc R . . C4 C 0.6414(2) 0.51876(15) 0.15045(13) 0.0215(3) Uani 1 1 d . . . C5 C 0.7959(2) 0.73489(15) 0.16564(14) 0.0242(3) Uani 1 1 d . . . H5 H 0.8329 0.8240 0.1711 0.029 Uiso 1 1 calc R . . C6 C 0.5072(2) 0.41223(16) 0.14419(14) 0.0255(3) Uani 1 1 d . . . C7 C 0.5550(3) 0.27940(17) 0.14130(18) 0.0359(4) Uani 1 1 d . . . H7A H 0.6240 0.2653 0.2187 0.054 Uiso 1 1 calc R . . H7B H 0.6242 0.2686 0.0891 0.054 Uiso 1 1 calc R . . H7C H 0.4482 0.2173 0.1142 0.054 Uiso 1 1 calc R . . C8 C 1.12295(19) 0.77014(15) 0.09447(13) 0.0207(3) Uani 1 1 d . . . C9 C 1.01990(19) 0.75987(14) -0.02279(13) 0.0205(3) Uani 1 1 d . . . H9 H 0.9247 0.6940 -0.0586 0.025 Uiso 1 1 calc R . . C10 C 1.07179(19) 0.85486(15) -0.07930(13) 0.0213(3) Uani 1 1 d . . . C11 C 1.2507(2) 0.87425(16) 0.12396(14) 0.0238(3) Uani 1 1 d . . . H11 H 1.3324 0.8969 0.1989 0.029 Uiso 1 1 calc R . . C12 C 0.9979(2) 0.87518(16) -0.19999(14) 0.0257(3) Uani 1 1 d . . . C13 C 0.8438(3) 0.7828(2) -0.27436(17) 0.0455(5) Uani 1 1 d . . . H13A H 0.8357 0.7846 -0.3552 0.068 Uiso 1 1 calc R . . H13B H 0.7365 0.8072 -0.2624 0.068 Uiso 1 1 calc R . . H13C H 0.8583 0.6963 -0.2540 0.068 Uiso 1 1 calc R . . C14 C 1.20646(19) 0.70571(16) 0.29521(13) 0.0237(3) Uani 1 1 d . . . C15 C 1.2034(2) 0.81763(17) 0.36740(13) 0.0255(3) Uani 1 1 d . . . H15 H 1.1298 0.8807 0.3425 0.031 Uiso 1 1 calc R . . C16 C 1.3180(2) 0.82465(17) 0.47670(14) 0.0290(4) Uani 1 1 d . . . C17 C 1.3232(2) 0.63054(17) 0.35320(15) 0.0294(4) Uani 1 1 d . . . H17 H 1.3428 0.5517 0.3194 0.035 Uiso 1 1 calc R . . C18 C 1.3591(2) 0.92617(19) 0.57423(15) 0.0338(4) Uani 1 1 d . . . C19 C 1.2548(3) 1.0350(2) 0.56332(17) 0.0407(5) Uani 1 1 d . . . H19A H 1.1572 1.0160 0.5933 0.061 Uiso 1 1 calc R . . H19B H 1.2090 1.0476 0.4822 0.061 Uiso 1 1 calc R . . H19C H 1.3296 1.1130 0.6072 0.061 Uiso 1 1 calc R . . O4 O 0.1036(5) 0.6529(4) 0.6290(3) 0.0616(11) Uani 0.500(3) 1 d P A -1 C21 C -0.1311(8) 0.6057(7) 0.4546(5) 0.0534(15) Uani 0.500(3) 1 d PD A -1 H21A H -0.1494 0.6943 0.4720 0.080 Uiso 0.500(3) 1 calc PR A -1 H21B H -0.2355 0.5476 0.4511 0.080 Uiso 0.500(3) 1 calc PR A -1 H21C H -0.1097 0.5952 0.3804 0.080 Uiso 0.500(3) 1 calc PR A -1 C20 C 0.0254(6) 0.5749(4) 0.5479(4) 0.0408(10) Uani 0.500(3) 1 d PD A -1 C22 C 0.0805(8) 0.4441(5) 0.5339(5) 0.0502(13) Uani 0.500(3) 1 d PD A -1 H22A H 0.1847 0.4375 0.5983 0.075 Uiso 0.500(3) 1 calc PR A -1 H22B H 0.1073 0.4317 0.4616 0.075 Uiso 0.500(3) 1 calc PR A -1 H22C H -0.0147 0.3784 0.5327 0.075 Uiso 0.500(3) 1 calc PR A -1 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0252(6) 0.0286(7) 0.0414(7) -0.0022(5) 0.0122(5) -0.0053(5) O2 0.0420(7) 0.0265(6) 0.0333(6) 0.0095(5) 0.0123(6) -0.0015(5) O3 0.0585(10) 0.0447(9) 0.0290(7) 0.0011(6) -0.0091(7) -0.0122(7) S1 0.02178(19) 0.0200(2) 0.0357(2) 0.00317(15) 0.00948(16) 0.00120(14) S2 0.02463(19) 0.01784(19) 0.0277(2) -0.00035(14) 0.00844(15) -0.00440(13) S3 0.0320(2) 0.0356(3) 0.0289(2) 0.00943(18) -0.00445(17) -0.00164(18) C1 0.0194(6) 0.0207(7) 0.0222(7) 0.0035(5) 0.0040(5) 0.0002(5) C2 0.0197(6) 0.0200(7) 0.0199(6) 0.0023(5) 0.0046(5) -0.0011(5) C3 0.0227(7) 0.0188(7) 0.0231(7) 0.0019(5) 0.0051(6) -0.0019(5) C4 0.0225(7) 0.0163(7) 0.0233(7) 0.0007(5) 0.0053(6) -0.0012(5) C5 0.0229(7) 0.0180(7) 0.0300(8) 0.0025(6) 0.0075(6) -0.0016(5) C6 0.0261(7) 0.0213(8) 0.0262(7) 0.0001(6) 0.0073(6) -0.0045(6) C7 0.0366(9) 0.0196(8) 0.0490(11) 0.0025(7) 0.0127(8) -0.0033(7) C8 0.0183(6) 0.0198(7) 0.0231(7) 0.0018(5) 0.0058(5) 0.0012(5) C9 0.0184(6) 0.0179(7) 0.0238(7) 0.0011(5) 0.0060(5) -0.0004(5) C10 0.0202(7) 0.0183(7) 0.0243(7) 0.0007(5) 0.0066(6) 0.0004(5) C11 0.0214(7) 0.0232(8) 0.0236(7) -0.0008(6) 0.0053(6) -0.0017(6) C12 0.0265(7) 0.0236(8) 0.0263(8) 0.0042(6) 0.0077(6) 0.0009(6) C13 0.0426(11) 0.0526(13) 0.0277(9) 0.0113(9) -0.0024(8) -0.0176(9) C14 0.0186(7) 0.0266(8) 0.0234(7) 0.0042(6) 0.0041(6) -0.0016(6) C15 0.0219(7) 0.0289(8) 0.0223(7) 0.0041(6) 0.0039(6) -0.0031(6) C16 0.0279(8) 0.0297(9) 0.0248(8) 0.0052(6) 0.0044(6) -0.0065(6) C17 0.0259(8) 0.0286(9) 0.0286(8) 0.0062(7) 0.0019(6) -0.0003(6) C18 0.0367(9) 0.0341(10) 0.0249(8) 0.0029(7) 0.0076(7) -0.0143(7) C19 0.0449(11) 0.0442(12) 0.0296(9) -0.0043(8) 0.0129(8) -0.0046(9) O4 0.064(2) 0.054(2) 0.050(2) -0.0052(16) -0.0031(16) 0.0059(17) C21 0.056(4) 0.065(4) 0.033(2) 0.015(3) 0.005(2) 0.008(3) C20 0.043(2) 0.047(2) 0.033(2) 0.0081(17) 0.0163(18) -0.0012(18) C22 0.054(4) 0.054(4) 0.047(3) 0.006(3) 0.023(3) 0.003(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 O1 C6 1.229(2) . ? O2 C12 1.218(2) . ? O3 C18 1.221(2) . ? S1 C5 1.7035(16) . ? S1 C4 1.7196(16) . ? S2 C11 1.7084(17) . ? S2 C10 1.7225(15) . ? S3 C17 1.7072(18) . ? S3 C16 1.726(2) . ? C1 C14 1.513(2) . ? C1 C8 1.517(2) . ? C1 C2 1.521(2) . ? C2 C5 1.370(2) . ? C2 C3 1.421(2) . ? C3 C4 1.379(2) . ? C4 C6 1.462(2) . ? C6 C7 1.497(2) . ? C8 C11 1.372(2) . ? C8 C9 1.419(2) . ? C9 C10 1.373(2) . ? C10 C12 1.468(2) . ? C12 C13 1.499(2) . ? C14 C17 1.372(2) . ? C14 C15 1.425(2) . ? C15 C16 1.373(2) . ? C16 C18 1.472(3) . ? C18 C19 1.490(3) . ? O4 C20 1.202(5) . ? C21 C20 1.516(6) . ? C20 C22 1.510(6) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C5 S1 C4 91.65(8) . . ? C11 S2 C10 91.54(8) . . ? C17 S3 C16 91.56(8) . . ? C14 C1 C8 113.27(13) . . ? C14 C1 C2 110.53(13) . . ? C8 C1 C2 111.42(12) . . ? C5 C2 C3 111.60(14) . . ? C5 C2 C1 124.60(14) . . ? C3 C2 C1 123.77(14) . . ? C4 C3 C2 112.57(14) . . ? C3 C4 C6 129.90(15) . . ? C3 C4 S1 111.35(11) . . ? C6 C4 S1 118.73(12) . . ? C2 C5 S1 112.83(12) . . ? O1 C6 C4 120.19(15) . . ? O1 C6 C7 121.44(15) . . ? C4 C6 C7 118.35(15) . . ? C11 C8 C9 111.41(14) . . ? C11 C8 C1 126.82(14) . . ? C9 C8 C1 121.69(13) . . ? C10 C9 C8 113.11(13) . . ? C9 C10 C12 128.67(14) . . ? C9 C10 S2 111.22(12) . . ? C12 C10 S2 120.10(12) . . ? C8 C11 S2 112.72(12) . . ? O2 C12 C10 120.89(15) . . ? O2 C12 C13 121.42(16) . . ? C10 C12 C13 117.69(15) . . ? C17 C14 C15 111.41(15) . . ? C17 C14 C1 123.39(15) . . ? C15 C14 C1 125.19(14) . . ? C16 C15 C14 112.90(16) . . ? C15 C16 C18 129.64(18) . . ? C15 C16 S3 111.31(13) . . ? C18 C16 S3 119.00(14) . . ? C14 C17 S3 112.82(14) . . ? O3 C18 C16 120.0(2) . . ? O3 C18 C19 120.93(18) . . ? C16 C18 C19 119.08(16) . . ? O4 C20 C22 121.6(5) . . ? O4 C20 C21 120.8(5) . . ? C22 C20 C21 117.6(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 C14 C1 C2 C5 80.70(19) . . . . ? C8 C1 C2 C5 -46.2(2) . . . . ? C14 C1 C2 C3 -96.97(17) . . . . ? C8 C1 C2 C3 136.16(15) . . . . ? C5 C2 C3 C4 -0.53(19) . . . . ? C1 C2 C3 C4 177.41(14) . . . . ? C2 C3 C4 C6 -178.53(15) . . . . ? C2 C3 C4 S1 0.21(17) . . . . ? C5 S1 C4 C3 0.12(12) . . . . ? C5 S1 C4 C6 179.02(13) . . . . ? C3 C2 C5 S1 0.62(18) . . . . ? C1 C2 C5 S1 -177.30(12) . . . . ? C4 S1 C5 C2 -0.43(13) . . . . ? C3 C4 C6 O1 179.70(16) . . . . ? S1 C4 C6 O1 1.0(2) . . . . ? C3 C4 C6 C7 1.2(3) . . . . ? S1 C4 C6 C7 -177.49(13) . . . . ? C14 C1 C8 C11 8.6(2) . . . . ? C2 C1 C8 C11 134.01(16) . . . . ? C14 C1 C8 C9 -174.82(14) . . . . ? C2 C1 C8 C9 -49.45(19) . . . . ? C11 C8 C9 C10 0.39(19) . . . . ? C1 C8 C9 C10 -176.63(14) . . . . ? C8 C9 C10 C12 179.74(15) . . . . ? C8 C9 C10 S2 -0.49(17) . . . . ? C11 S2 C10 C9 0.36(12) . . . . ? C11 S2 C10 C12 -179.85(13) . . . . ? C9 C8 C11 S2 -0.11(17) . . . . ? C1 C8 C11 S2 176.73(12) . . . . ? C10 S2 C11 C8 -0.14(13) . . . . ? C9 C10 C12 O2 -179.78(16) . . . . ? S2 C10 C12 O2 0.5(2) . . . . ? C9 C10 C12 C13 0.7(3) . . . . ? S2 C10 C12 C13 -179.05(15) . . . . ? C8 C1 C14 C17 -121.31(17) . . . . ? C2 C1 C14 C17 112.84(18) . . . . ? C8 C1 C14 C15 59.9(2) . . . . ? C2 C1 C14 C15 -65.9(2) . . . . ? C17 C14 C15 C16 0.6(2) . . . . ? C1 C14 C15 C16 179.48(15) . . . . ? C14 C15 C16 C18 177.12(17) . . . . ? C14 C15 C16 S3 -0.42(18) . . . . ? C17 S3 C16 C15 0.13(14) . . . . ? C17 S3 C16 C18 -177.70(14) . . . . ? C15 C14 C17 S3 -0.46(19) . . . . ? C1 C14 C17 S3 -179.40(12) . . . . ? C16 S3 C17 C14 0.19(14) . . . . ? C15 C16 C18 O3 -173.86(19) . . . . ? S3 C16 C18 O3 3.5(2) . . . . ? C15 C16 C18 C19 6.6(3) . . . . ? S3 C16 C18 C19 -176.01(14) . . . . ? H1 C1 C2 C5 -163.0 . . . . ? H1 C1 C8 C11 -109.2 . . . . ? H1 C1 C14 C17 -3.5 . . . . ? _diffrn_measured_fraction_theta_max 0.979 _diffrn_reflns_theta_full 29.61 _diffrn_measured_fraction_theta_full 0.979 _refine_diff_density_max 0.549 _refine_diff_density_min -0.426 _refine_diff_density_rms 0.074 data_1b _database_code_depnum_ccdc_archive 'CCDC 677793' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '2(C19H16O3S3) 0.80(C3H6O1)' _chemical_formula_sum 'C40.40 H36.80 O6.80 S6' _chemical_formula_weight 823.46 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 8.0791(10) _cell_length_b 10.6375(13) _cell_length_c 12.2629(15) _cell_angle_alpha 95.240(2) _cell_angle_beta 107.497(2) _cell_angle_gamma 95.945(3) _cell_volume 991.4(2) _cell_formula_units_Z 1 _cell_measurement_temperature 125(2) _cell_measurement_reflns_used 3654 _cell_measurement_theta_min 1.76 _cell_measurement_theta_max 24.88 _exptl_crystal_description plate _exptl_crystal_colour 'pale yellow' _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.379 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 430 _exptl_absorpt_coefficient_mu 0.393 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8844 _exptl_absorpt_correction_T_max 0.9617 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 125(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 'Bruker SMART 1000 CCD' _diffrn_measurement_method '/w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5002 _diffrn_reflns_av_R_equivalents 0.0156 _diffrn_reflns_av_sigmaI/netI 0.0258 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.76 _diffrn_reflns_theta_max 25.03 _reflns_number_total 3352 _reflns_number_gt 3027 _reflns_threshold_expression >2sigma(I) _computing_data_collection SMART _computing_cell_refinement 'SAINT (Bruker 2001)' _computing_data_reduction 'SAINT (Bruker 2001)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _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^)+(0.0473P)^2^+0.8764P] 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 3352 _refine_ls_number_parameters 268 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0413 _refine_ls_R_factor_gt 0.0370 _refine_ls_wR_factor_ref 0.1003 _refine_ls_wR_factor_gt 0.0970 _refine_ls_goodness_of_fit_ref 1.045 _refine_ls_restrained_S_all 1.046 _refine_ls_shift/su_max 0.006 _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 O1 O -0.6402(2) -0.06718(15) 0.14440(14) 0.0343(4) Uani 1 1 d . . . O2 O 0.0592(2) 0.46480(15) -0.23896(14) 0.0358(4) Uani 1 1 d . . . O3 O 0.4753(3) 0.42131(18) 0.66448(15) 0.0523(5) Uani 1 1 d . . . S1 S -0.41168(7) 0.17177(5) 0.15910(5) 0.02779(16) Uani 1 1 d . . . S2 S 0.24682(7) 0.45867(5) 0.01076(5) 0.02601(15) Uani 1 1 d . . . S3 S 0.42584(8) 0.19434(6) 0.49391(5) 0.03807(18) Uani 1 1 d . . . C1 C 0.0939(3) 0.1720(2) 0.17060(18) 0.0237(4) Uani 1 1 d . . . H1 H 0.1285 0.0912 0.1414 0.028 Uiso 1 1 calc R . . C2 C -0.0987(3) 0.14385(19) 0.16185(17) 0.0225(4) Uani 1 1 d . . . C3 C -0.1875(3) 0.0188(2) 0.15304(17) 0.0235(4) Uani 1 1 d . . . H3 H -0.1345 -0.0564 0.1489 0.028 Uiso 1 1 calc R . . C4 C -0.3589(3) 0.01906(19) 0.15110(18) 0.0240(4) Uani 1 1 d . . . C5 C -0.2058(3) 0.2347(2) 0.16482(19) 0.0261(5) Uani 1 1 d . . . H5 H -0.1694 0.3234 0.1696 0.031 Uiso 1 1 calc R . . C6 C -0.4929(3) -0.0869(2) 0.14530(18) 0.0272(5) Uani 1 1 d . . . C7 C -0.4441(3) -0.2188(2) 0.1429(2) 0.0375(6) Uani 1 1 d . . . H7A H -0.3670 -0.2297 0.2192 0.056 Uiso 1 1 calc R . . H7B H -0.3829 -0.2321 0.0857 0.056 Uiso 1 1 calc R . . H7C H -0.5503 -0.2811 0.1222 0.056 Uiso 1 1 calc R . . C8 C 0.1229(3) 0.27044(19) 0.09395(18) 0.0224(4) Uani 1 1 d . . . C9 C 0.0202(3) 0.26022(19) -0.02371(18) 0.0222(4) Uani 1 1 d . . . H9 H -0.0748 0.1944 -0.0597 0.027 Uiso 1 1 calc R . . C10 C 0.0715(3) 0.35445(19) -0.08023(18) 0.0228(4) Uani 1 1 d . . . C11 C 0.2501(3) 0.3740(2) 0.12368(18) 0.0262(5) Uani 1 1 d . . . H11 H 0.3315 0.3966 0.1988 0.031 Uiso 1 1 calc R . . C12 C -0.0016(3) 0.3750(2) -0.20117(19) 0.0290(5) Uani 1 1 d . . . C13 C -0.1540(4) 0.2825(3) -0.2758(2) 0.0514(8) Uani 1 1 d . . . H13A H -0.2632 0.3118 -0.2715 0.077 Uiso 1 1 calc R . . H13B H -0.1462 0.1985 -0.2492 0.077 Uiso 1 1 calc R . . H13C H -0.1527 0.2763 -0.3558 0.077 Uiso 1 1 calc R . . C14 C 0.2058(3) 0.2069(2) 0.29559(18) 0.0252(5) Uani 1 1 d . . . C15 C 0.2037(3) 0.3189(2) 0.36809(18) 0.0266(5) Uani 1 1 d . . . H15 H 0.1313 0.3822 0.3429 0.032 Uiso 1 1 calc R . . C16 C 0.3166(3) 0.3261(2) 0.47781(19) 0.0298(5) Uani 1 1 d . . . C17 C 0.3203(3) 0.1316(2) 0.3538(2) 0.0310(5) Uani 1 1 d . . . H17 H 0.3392 0.0526 0.3198 0.037 Uiso 1 1 calc R . . C18 C 0.3587(3) 0.4278(2) 0.5757(2) 0.0353(6) Uani 1 1 d . . . C19 C 0.2573(4) 0.5374(3) 0.5642(2) 0.0421(6) Uani 1 1 d . . . H19A H 0.1606 0.5214 0.5961 0.063 Uiso 1 1 calc R . . H19B H 0.2100 0.5479 0.4825 0.063 Uiso 1 1 calc R . . H19C H 0.3344 0.6151 0.6063 0.063 Uiso 1 1 calc R . . O4 O 0.1006(7) 0.1510(5) 0.6313(4) 0.0593(14) Uani 0.40 1 d P A -1 C20 C 0.0235(9) 0.0741(6) 0.5478(6) 0.0384(14) Uani 0.40 1 d PD A -1 C21 C 0.0775(13) -0.0568(8) 0.5323(9) 0.048(2) Uani 0.40 1 d PD A -1 H21A H 0.1863 -0.0621 0.5935 0.072 Uiso 0.40 1 calc PR A -1 H21B H 0.0964 -0.0712 0.4571 0.072 Uiso 0.40 1 calc PR A -1 H21C H -0.0151 -0.1217 0.5362 0.072 Uiso 0.40 1 calc PR A -1 C22 C -0.1328(12) 0.1041(11) 0.4532(8) 0.052(2) Uani 0.40 1 d PD A -1 H22A H -0.1496 0.1931 0.4690 0.079 Uiso 0.40 1 calc PR A -1 H22B H -0.2382 0.0479 0.4508 0.079 Uiso 0.40 1 calc PR A -1 H22C H -0.1115 0.0907 0.3787 0.079 Uiso 0.40 1 calc PR A -1 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0227(8) 0.0332(9) 0.0421(9) -0.0049(7) 0.0088(7) -0.0055(7) O2 0.0391(10) 0.0319(9) 0.0348(9) 0.0094(7) 0.0096(8) -0.0013(7) O3 0.0565(13) 0.0481(11) 0.0301(10) 0.0015(8) -0.0124(9) -0.0101(9) S1 0.0209(3) 0.0234(3) 0.0370(3) 0.0013(2) 0.0073(2) 0.0017(2) S2 0.0226(3) 0.0216(3) 0.0297(3) -0.0022(2) 0.0060(2) -0.0039(2) S3 0.0317(3) 0.0390(3) 0.0310(3) 0.0076(3) -0.0079(2) -0.0009(3) C1 0.0192(10) 0.0236(10) 0.0242(10) -0.0009(8) 0.0022(8) 0.0017(8) C2 0.0201(10) 0.0233(10) 0.0194(10) 0.0000(8) 0.0009(8) 0.0008(8) C3 0.0202(10) 0.0245(10) 0.0211(10) 0.0009(8) 0.0014(8) -0.0008(8) C4 0.0243(11) 0.0205(10) 0.0232(10) -0.0004(8) 0.0030(8) 0.0009(8) C5 0.0229(11) 0.0224(10) 0.0297(11) 0.0019(9) 0.0048(9) -0.0004(8) C6 0.0229(11) 0.0278(11) 0.0256(11) -0.0021(9) 0.0035(9) -0.0031(9) C7 0.0349(13) 0.0232(11) 0.0515(15) 0.0012(10) 0.0129(12) -0.0038(10) C8 0.0170(10) 0.0233(10) 0.0245(10) -0.0018(8) 0.0043(8) 0.0029(8) C9 0.0144(9) 0.0223(10) 0.0260(10) -0.0021(8) 0.0025(8) 0.0007(8) C10 0.0168(10) 0.0223(10) 0.0261(11) -0.0018(8) 0.0040(8) 0.0012(8) C11 0.0215(11) 0.0270(11) 0.0253(11) -0.0021(9) 0.0032(9) -0.0009(9) C12 0.0264(11) 0.0283(11) 0.0307(12) 0.0047(9) 0.0066(9) 0.0029(9) C13 0.0433(16) 0.0631(18) 0.0311(13) 0.0151(13) -0.0076(12) -0.0180(14) C14 0.0167(10) 0.0306(11) 0.0245(11) 0.0047(9) 0.0023(8) -0.0017(8) C15 0.0193(10) 0.0314(11) 0.0247(11) 0.0036(9) 0.0024(9) -0.0023(9) C16 0.0248(11) 0.0332(12) 0.0262(11) 0.0048(9) 0.0032(9) -0.0054(9) C17 0.0248(11) 0.0323(12) 0.0300(12) 0.0044(9) 0.0007(9) 0.0003(9) C18 0.0334(13) 0.0391(13) 0.0258(12) 0.0039(10) 0.0043(10) -0.0139(10) C19 0.0427(15) 0.0477(15) 0.0307(13) -0.0060(11) 0.0099(11) -0.0021(12) O4 0.058(3) 0.064(3) 0.043(3) -0.004(3) 0.000(3) 0.007(3) C20 0.036(4) 0.051(4) 0.028(4) 0.007(3) 0.011(3) 0.000(3) C21 0.040(6) 0.060(6) 0.046(6) 0.011(5) 0.018(5) 0.002(4) C22 0.043(6) 0.078(8) 0.026(4) 0.010(4) -0.005(4) 0.007(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C6 1.227(3) . ? O2 C12 1.220(3) . ? O3 C18 1.220(3) . ? S1 C5 1.706(2) . ? S1 C4 1.723(2) . ? S2 C11 1.715(2) . ? S2 C10 1.726(2) . ? S3 C17 1.708(2) . ? S3 C16 1.727(2) . ? C1 C14 1.516(3) . ? C1 C8 1.515(3) . ? C1 C2 1.523(3) . ? C2 C5 1.367(3) . ? C2 C3 1.423(3) . ? C3 C4 1.379(3) . ? C4 C6 1.461(3) . ? C6 C7 1.497(3) . ? C8 C11 1.367(3) . ? C8 C9 1.420(3) . ? C9 C10 1.368(3) . ? C10 C12 1.468(3) . ? C12 C13 1.493(3) . ? C14 C17 1.367(3) . ? C14 C15 1.425(3) . ? C15 C16 1.370(3) . ? C16 C18 1.472(3) . ? C18 C19 1.486(4) . ? O4 C20 1.209(9) . ? C20 C21 1.515(8) . ? C20 C22 1.521(7) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C5 S1 C4 91.53(10) . . ? C11 S2 C10 91.28(10) . . ? C17 S3 C16 91.55(11) . . ? C14 C1 C8 113.46(17) . . ? C14 C1 C2 110.35(17) . . ? C8 C1 C2 111.60(16) . . ? C5 C2 C3 111.78(19) . . ? C5 C2 C1 124.56(18) . . ? C3 C2 C1 123.63(18) . . ? C4 C3 C2 112.47(19) . . ? C3 C4 C6 130.1(2) . . ? C3 C4 S1 111.38(16) . . ? C6 C4 S1 118.50(16) . . ? C2 C5 S1 112.82(16) . . ? O1 C6 C4 120.4(2) . . ? O1 C6 C7 121.4(2) . . ? C4 C6 C7 118.17(19) . . ? C11 C8 C9 111.35(19) . . ? C11 C8 C1 126.70(19) . . ? C9 C8 C1 121.88(18) . . ? C10 C9 C8 113.36(19) . . ? C9 C10 C12 129.06(19) . . ? C9 C10 S2 111.23(16) . . ? C12 C10 S2 119.71(16) . . ? C8 C11 S2 112.78(16) . . ? O2 C12 C10 121.2(2) . . ? O2 C12 C13 121.3(2) . . ? C10 C12 C13 117.5(2) . . ? C17 C14 C15 111.31(19) . . ? C17 C14 C1 123.4(2) . . ? C15 C14 C1 125.29(19) . . ? C16 C15 C14 113.2(2) . . ? C15 C16 C18 129.9(2) . . ? C15 C16 S3 111.01(17) . . ? C18 C16 S3 119.01(17) . . ? C14 C17 S3 112.89(18) . . ? O3 C18 C16 120.0(2) . . ? O3 C18 C19 121.0(2) . . ? C16 C18 C19 119.0(2) . . ? O4 C20 C21 121.7(7) . . ? O4 C20 C22 121.6(7) . . ? C21 C20 C22 116.6(9) . . ? 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 C14 C1 C2 C5 81.5(2) . . . . ? C8 C1 C2 C5 -45.6(3) . . . . ? C14 C1 C2 C3 -96.5(2) . . . . ? C8 C1 C2 C3 136.4(2) . . . . ? C5 C2 C3 C4 -0.8(3) . . . . ? C1 C2 C3 C4 177.45(18) . . . . ? C2 C3 C4 C6 -178.6(2) . . . . ? C2 C3 C4 S1 0.4(2) . . . . ? C5 S1 C4 C3 0.06(17) . . . . ? C5 S1 C4 C6 179.18(17) . . . . ? C3 C2 C5 S1 0.8(2) . . . . ? C1 C2 C5 S1 -177.39(16) . . . . ? C4 S1 C5 C2 -0.52(17) . . . . ? C3 C4 C6 O1 -180.0(2) . . . . ? S1 C4 C6 O1 1.1(3) . . . . ? C3 C4 C6 C7 1.2(3) . . . . ? S1 C4 C6 C7 -177.72(17) . . . . ? C14 C1 C8 C11 8.5(3) . . . . ? C2 C1 C8 C11 133.9(2) . . . . ? C14 C1 C8 C9 -174.69(18) . . . . ? C2 C1 C8 C9 -49.3(3) . . . . ? C11 C8 C9 C10 0.4(3) . . . . ? C1 C8 C9 C10 -176.89(18) . . . . ? C8 C9 C10 C12 179.7(2) . . . . ? C8 C9 C10 S2 -0.5(2) . . . . ? C11 S2 C10 C9 0.31(16) . . . . ? C11 S2 C10 C12 -179.82(17) . . . . ? C9 C8 C11 S2 -0.2(2) . . . . ? C1 C8 C11 S2 176.98(16) . . . . ? C10 S2 C11 C8 -0.09(17) . . . . ? C9 C10 C12 O2 179.8(2) . . . . ? S2 C10 C12 O2 -0.1(3) . . . . ? C9 C10 C12 C13 0.3(4) . . . . ? S2 C10 C12 C13 -179.56(19) . . . . ? C8 C1 C14 C17 -122.2(2) . . . . ? C2 C1 C14 C17 111.7(2) . . . . ? C8 C1 C14 C15 59.2(3) . . . . ? C2 C1 C14 C15 -66.9(3) . . . . ? C17 C14 C15 C16 0.6(3) . . . . ? C1 C14 C15 C16 179.3(2) . . . . ? C14 C15 C16 C18 176.8(2) . . . . ? C14 C15 C16 S3 -0.5(2) . . . . ? C17 S3 C16 C15 0.25(18) . . . . ? C17 S3 C16 C18 -177.41(19) . . . . ? C15 C14 C17 S3 -0.4(2) . . . . ? C1 C14 C17 S3 -179.11(16) . . . . ? C16 S3 C17 C14 0.07(19) . . . . ? C15 C16 C18 O3 -173.5(2) . . . . ? S3 C16 C18 O3 3.6(3) . . . . ? C15 C16 C18 C19 6.4(4) . . . . ? S3 C16 C18 C19 -176.40(18) . . . . ? H1 C1 C2 C5 -162.4 . . . . ? H1 C1 C8 C11 -109.4 . . . . ? H1 C1 C14 C17 -4.4 . . . . ? _diffrn_measured_fraction_theta_max 0.958 _diffrn_reflns_theta_full 25.03 _diffrn_measured_fraction_theta_full 0.958 _refine_diff_density_max 0.559 _refine_diff_density_min -0.419 _refine_diff_density_rms 0.050 data_1bB _database_code_depnum_ccdc_archive 'CCDC 677794' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '2(C19H16O3S3) 0.96(C3H6O1)' _chemical_formula_sum 'C40.88 H37.76 O6.96 S6' _chemical_formula_weight 832.75 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 8.1349(6) _cell_length_b 10.5100(8) _cell_length_c 12.3775(9) _cell_angle_alpha 94.6240(10) _cell_angle_beta 108.2740(10) _cell_angle_gamma 95.7780(10) _cell_volume 992.70(13) _cell_formula_units_Z 1 _cell_measurement_temperature 125(2) _cell_measurement_reflns_used 6104 _cell_measurement_theta_min 1.74 _cell_measurement_theta_max 28.25 _exptl_crystal_description PLATE _exptl_crystal_colour 'PALE YELLOW' _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.393 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 435 _exptl_absorpt_coefficient_mu 0.394 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8843 _exptl_absorpt_correction_T_max 0.9617 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 125(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 'Bruker SMART 1000 CCD' _diffrn_measurement_method '/w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12349 _diffrn_reflns_av_R_equivalents 0.0159 _diffrn_reflns_av_sigmaI/netI 0.0209 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.74 _diffrn_reflns_theta_max 29.57 _reflns_number_total 5497 _reflns_number_gt 4680 _reflns_threshold_expression >2sigma(I) _computing_data_collection SMART _computing_cell_refinement 'SAINT (Bruker 2001)' _computing_data_reduction 'SAINT (Bruker 2001)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _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^)+(0.0531P)^2^+0.3042P] 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 5497 _refine_ls_number_parameters 268 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0408 _refine_ls_R_factor_gt 0.0325 _refine_ls_wR_factor_ref 0.0937 _refine_ls_wR_factor_gt 0.0872 _refine_ls_goodness_of_fit_ref 1.031 _refine_ls_restrained_S_all 1.033 _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 O1 O -0.63983(13) -0.06631(10) 0.64314(9) 0.0317(2) Uani 1 1 d . . . O2 O 0.06053(14) 0.46258(10) 0.26190(9) 0.0329(2) Uani 1 1 d . . . O3 O 0.48109(18) 0.41964(13) 1.16115(10) 0.0491(3) Uani 1 1 d . . . S1 S 0.24491(4) 0.45824(3) 0.51182(3) 0.02284(8) Uani 1 1 d . . . S2 S -0.40940(4) 0.17375(3) 0.65943(3) 0.02476(8) Uani 1 1 d . . . S3 S 0.43304(5) 0.19218(4) 0.99234(3) 0.03457(10) Uani 1 1 d . . . C1 C 0.09239(15) 0.16956(12) 0.67203(10) 0.0202(2) Uani 1 1 d . . . H1 H 0.1258 0.0874 0.6438 0.024 Uiso 1 1 calc R . . C2 C -0.09897(15) 0.14276(12) 0.66278(10) 0.0194(2) Uani 1 1 d . . . C3 C -0.18920(16) 0.01730(12) 0.65339(10) 0.0210(2) Uani 1 1 d . . . H3 H -0.1377 -0.0594 0.6493 0.025 Uiso 1 1 calc R . . C4 C -0.35940(16) 0.01895(12) 0.65092(10) 0.0208(2) Uani 1 1 d . . . C5 C -0.20421(16) 0.23601(12) 0.66602(11) 0.0231(2) Uani 1 1 d . . . H5 H -0.1669 0.3256 0.6714 0.028 Uiso 1 1 calc R . . C6 C -0.49395(17) -0.08789(13) 0.64436(11) 0.0244(3) Uani 1 1 d . . . C7 C -0.4463(2) -0.22179(14) 0.64215(14) 0.0340(3) Uani 1 1 d . . . H7A H -0.3733 -0.2352 0.7189 0.051 Uiso 1 1 calc R . . H7B H -0.3816 -0.2338 0.5882 0.051 Uiso 1 1 calc R . . H7C H -0.5529 -0.2840 0.6179 0.051 Uiso 1 1 calc R . . C8 C 0.20583(15) 0.20419(13) 0.79615(11) 0.0223(2) Uani 1 1 d . . . C9 C 0.20294(16) 0.31619(13) 0.86777(11) 0.0243(3) Uani 1 1 d . . . H9 H 0.1282 0.3794 0.8429 0.029 Uiso 1 1 calc R . . C10 C 0.31956(17) 0.32357(14) 0.97671(11) 0.0269(3) Uani 1 1 d . . . C11 C 0.32461(17) 0.12899(14) 0.85351(12) 0.0283(3) Uani 1 1 d . . . H11 H 0.3446 0.0501 0.8197 0.034 Uiso 1 1 calc R . . C12 C 0.3611(2) 0.42510(15) 1.07359(12) 0.0324(3) Uani 1 1 d . . . C13 C 0.2540(2) 0.53353(17) 1.06316(14) 0.0398(4) Uani 1 1 d . . . H13A H 0.1576 0.5125 1.0931 0.060 Uiso 1 1 calc R . . H13B H 0.2067 0.5471 0.9824 0.060 Uiso 1 1 calc R . . H13C H 0.3273 0.6122 1.1072 0.060 Uiso 1 1 calc R . . C14 C 0.12148(15) 0.26891(12) 0.59529(10) 0.0194(2) Uani 1 1 d . . . C15 C 0.01946(15) 0.25790(12) 0.47777(10) 0.0191(2) Uani 1 1 d . . . H15 H -0.0750 0.1915 0.4420 0.023 Uiso 1 1 calc R . . C16 C 0.07153(15) 0.35319(12) 0.42113(10) 0.0199(2) Uani 1 1 d . . . C17 C 0.24765(16) 0.37398(13) 0.62477(11) 0.0227(2) Uani 1 1 d . . . H17 H 0.3280 0.3975 0.6999 0.027 Uiso 1 1 calc R . . C18 C -0.00083(17) 0.37273(13) 0.30023(11) 0.0249(3) Uani 1 1 d . . . C19 C -0.1537(2) 0.27909(18) 0.22561(13) 0.0427(4) Uani 1 1 d . . . H19A H -0.2608 0.3009 0.2388 0.064 Uiso 1 1 calc R . . H19B H -0.1357 0.1916 0.2443 0.064 Uiso 1 1 calc R . . H19C H -0.1645 0.2837 0.1450 0.064 Uiso 1 1 calc R . . O4 O 1.1082(4) 0.1544(3) 0.1265(2) 0.0552(7) Uani 0.48 1 d P A -1 C20 C 1.0284(4) 0.0758(3) 0.0469(3) 0.0377(7) Uani 0.48 1 d PD A -1 C21 C 1.0820(7) -0.0558(4) 0.0340(5) 0.0475(11) Uani 0.48 1 d PD A -1 H21A H 1.1239 -0.0643 -0.0320 0.071 Uiso 0.48 1 calc PR A -1 H21B H 0.9815 -0.1214 0.0221 0.071 Uiso 0.48 1 calc PR A -1 H21C H 1.1757 -0.0675 0.1036 0.071 Uiso 0.48 1 calc PR A -1 C22 C 0.8712(6) 0.1062(6) -0.0453(4) 0.0490(11) Uani 0.48 1 d PD A -1 H22A H 0.8457 0.1923 -0.0248 0.073 Uiso 0.48 1 calc PR A -1 H22B H 0.7704 0.0425 -0.0530 0.073 Uiso 0.48 1 calc PR A -1 H22C H 0.8950 0.1036 -0.1183 0.073 Uiso 0.48 1 calc PR A -1 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0215(4) 0.0321(5) 0.0389(6) -0.0038(4) 0.0110(4) -0.0059(4) O2 0.0393(6) 0.0293(5) 0.0293(5) 0.0072(4) 0.0112(4) -0.0026(4) O3 0.0531(8) 0.0468(7) 0.0265(6) 0.0008(5) -0.0099(5) -0.0122(6) S1 0.02112(15) 0.02009(15) 0.02468(16) -0.00178(11) 0.00715(12) -0.00498(11) S2 0.01811(14) 0.02236(15) 0.03315(18) 0.00170(12) 0.00831(12) 0.00099(11) S3 0.02813(18) 0.0382(2) 0.02631(18) 0.00787(14) -0.00590(13) -0.00199(14) C1 0.0156(5) 0.0225(6) 0.0198(5) 0.0012(4) 0.0033(4) -0.0005(4) C2 0.0165(5) 0.0209(5) 0.0177(5) 0.0003(4) 0.0030(4) -0.0013(4) C3 0.0191(5) 0.0214(6) 0.0199(5) 0.0005(4) 0.0040(4) -0.0009(4) C4 0.0190(5) 0.0195(5) 0.0214(6) -0.0005(4) 0.0046(4) -0.0010(4) C5 0.0191(5) 0.0210(6) 0.0270(6) 0.0017(5) 0.0060(5) -0.0017(4) C6 0.0221(6) 0.0244(6) 0.0229(6) -0.0023(5) 0.0060(5) -0.0052(5) C7 0.0332(7) 0.0221(6) 0.0444(9) 0.0007(6) 0.0126(6) -0.0048(6) C8 0.0162(5) 0.0268(6) 0.0210(6) 0.0034(5) 0.0036(4) -0.0025(5) C9 0.0197(5) 0.0301(6) 0.0196(6) 0.0029(5) 0.0034(5) -0.0032(5) C10 0.0230(6) 0.0313(7) 0.0215(6) 0.0046(5) 0.0034(5) -0.0071(5) C11 0.0217(6) 0.0307(7) 0.0267(6) 0.0052(5) 0.0006(5) -0.0008(5) C12 0.0323(7) 0.0373(8) 0.0209(6) 0.0018(5) 0.0055(5) -0.0150(6) C13 0.0410(8) 0.0471(9) 0.0275(7) -0.0062(6) 0.0115(6) -0.0044(7) C14 0.0155(5) 0.0214(6) 0.0199(5) -0.0002(4) 0.0048(4) 0.0003(4) C15 0.0148(5) 0.0198(5) 0.0205(5) -0.0009(4) 0.0042(4) -0.0008(4) C16 0.0168(5) 0.0202(5) 0.0208(6) -0.0008(4) 0.0051(4) -0.0005(4) C17 0.0190(5) 0.0253(6) 0.0202(6) -0.0015(5) 0.0039(4) -0.0021(5) C18 0.0237(6) 0.0259(6) 0.0237(6) 0.0032(5) 0.0064(5) 0.0008(5) C19 0.0369(8) 0.0539(10) 0.0242(7) 0.0090(7) -0.0026(6) -0.0174(7) O4 0.0542(17) 0.0539(17) 0.0412(15) -0.0060(12) -0.0029(12) 0.0006(13) C20 0.0373(17) 0.0486(19) 0.0262(15) 0.0044(13) 0.0118(13) -0.0034(15) C21 0.052(3) 0.048(3) 0.047(3) 0.003(2) 0.024(2) 0.003(2) C22 0.046(3) 0.067(3) 0.0284(18) 0.009(2) 0.0043(17) 0.004(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 O1 C6 1.2261(16) . ? O2 C18 1.2214(17) . ? O3 C12 1.2201(18) . ? S1 C17 1.7098(13) . ? S1 C16 1.7210(12) . ? S2 C5 1.7050(13) . ? S2 C4 1.7193(13) . ? S3 C11 1.7086(15) . ? S3 C10 1.7275(15) . ? C1 C8 1.5157(17) . ? C1 C14 1.5165(17) . ? C1 C2 1.5200(16) . ? C2 C5 1.3709(17) . ? C2 C3 1.4205(17) . ? C3 C4 1.3771(17) . ? C4 C6 1.4655(17) . ? C6 C7 1.497(2) . ? C8 C11 1.3699(18) . ? C8 C9 1.4221(19) . ? C9 C10 1.3748(17) . ? C10 C12 1.469(2) . ? C12 C13 1.493(2) . ? C14 C17 1.3705(17) . ? C14 C15 1.4194(16) . ? C15 C16 1.3740(17) . ? C16 C18 1.4661(18) . ? C18 C19 1.502(2) . ? O4 C20 1.198(4) . ? C20 C21 1.502(5) . ? C20 C22 1.506(5) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C17 S1 C16 91.48(6) . . ? C5 S2 C4 91.69(6) . . ? C11 S3 C10 91.54(7) . . ? C8 C1 C14 113.24(10) . . ? C8 C1 C2 110.60(10) . . ? C14 C1 C2 111.65(10) . . ? C5 C2 C3 111.64(11) . . ? C5 C2 C1 124.50(11) . . ? C3 C2 C1 123.83(11) . . ? C4 C3 C2 112.67(11) . . ? C3 C4 C6 129.93(12) . . ? C3 C4 S2 111.33(9) . . ? C6 C4 S2 118.72(9) . . ? C2 C5 S2 112.66(10) . . ? O1 C6 C4 120.10(12) . . ? O1 C6 C7 121.71(12) . . ? C4 C6 C7 118.18(12) . . ? C11 C8 C9 111.51(12) . . ? C11 C8 C1 123.26(12) . . ? C9 C8 C1 125.22(11) . . ? C10 C9 C8 113.03(12) . . ? C9 C10 C12 129.80(14) . . ? C9 C10 S3 111.11(11) . . ? C12 C10 S3 119.06(11) . . ? C8 C11 S3 112.81(11) . . ? O3 C12 C10 119.99(15) . . ? O3 C12 C13 120.98(14) . . ? C10 C12 C13 119.03(13) . . ? C17 C14 C15 111.41(11) . . ? C17 C14 C1 126.90(11) . . ? C15 C14 C1 121.63(11) . . ? C16 C15 C14 113.02(11) . . ? C15 C16 C18 128.63(11) . . ? C15 C16 S1 111.32(9) . . ? C18 C16 S1 120.05(9) . . ? C14 C17 S1 112.77(9) . . ? O2 C18 C16 121.07(12) . . ? O2 C18 C19 121.27(13) . . ? C16 C18 C19 117.66(12) . . ? O4 C20 C21 121.7(4) . . ? O4 C20 C22 120.9(4) . . ? C21 C20 C22 117.4(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 C8 C1 C2 C5 80.62(15) . . . . ? C14 C1 C2 C5 -46.44(16) . . . . ? C8 C1 C2 C3 -97.24(14) . . . . ? C14 C1 C2 C3 135.70(12) . . . . ? C5 C2 C3 C4 -0.60(16) . . . . ? C1 C2 C3 C4 177.51(11) . . . . ? C2 C3 C4 C6 -178.61(12) . . . . ? C2 C3 C4 S2 0.27(14) . . . . ? C5 S2 C4 C3 0.09(10) . . . . ? C5 S2 C4 C6 179.11(11) . . . . ? C3 C2 C5 S2 0.67(14) . . . . ? C1 C2 C5 S2 -177.42(9) . . . . ? C4 S2 C5 C2 -0.44(10) . . . . ? C3 C4 C6 O1 179.97(13) . . . . ? S2 C4 C6 O1 1.17(17) . . . . ? C3 C4 C6 C7 1.4(2) . . . . ? S2 C4 C6 C7 -177.37(10) . . . . ? C14 C1 C8 C11 -119.64(13) . . . . ? C2 C1 C8 C11 114.18(14) . . . . ? C14 C1 C8 C9 60.82(16) . . . . ? C2 C1 C8 C9 -65.37(16) . . . . ? C11 C8 C9 C10 0.40(16) . . . . ? C1 C8 C9 C10 179.99(12) . . . . ? C8 C9 C10 C12 177.27(13) . . . . ? C8 C9 C10 S3 -0.37(14) . . . . ? C11 S3 C10 C9 0.20(11) . . . . ? C11 S3 C10 C12 -177.73(11) . . . . ? C9 C8 C11 S3 -0.24(15) . . . . ? C1 C8 C11 S3 -179.84(10) . . . . ? C10 S3 C11 C8 0.03(11) . . . . ? C9 C10 C12 O3 -173.24(15) . . . . ? S3 C10 C12 O3 4.25(19) . . . . ? C9 C10 C12 C13 7.1(2) . . . . ? S3 C10 C12 C13 -175.38(11) . . . . ? C8 C1 C14 C17 7.26(17) . . . . ? C2 C1 C14 C17 132.88(13) . . . . ? C8 C1 C14 C15 -175.82(11) . . . . ? C2 C1 C14 C15 -50.19(15) . . . . ? C17 C14 C15 C16 0.70(15) . . . . ? C1 C14 C15 C16 -176.66(11) . . . . ? C14 C15 C16 C18 179.50(12) . . . . ? C14 C15 C16 S1 -0.59(13) . . . . ? C17 S1 C16 C15 0.26(10) . . . . ? C17 S1 C16 C18 -179.82(11) . . . . ? C15 C14 C17 S1 -0.50(14) . . . . ? C1 C14 C17 S1 176.69(10) . . . . ? C16 S1 C17 C14 0.15(10) . . . . ? C15 C16 C18 O2 -179.71(13) . . . . ? S1 C16 C18 O2 0.39(18) . . . . ? C15 C16 C18 C19 0.8(2) . . . . ? S1 C16 C18 C19 -179.13(12) . . . . ? H1 C1 C2 C5 -163.2 . . . . ? H1 C1 C8 C11 -2.0 . . . . ? H1 C1 C14 C17 -110.4 . . . . ? _diffrn_measured_fraction_theta_max 0.984 _diffrn_reflns_theta_full 29.57 _diffrn_measured_fraction_theta_full 0.984 _refine_diff_density_max 0.509 _refine_diff_density_min -0.241 _refine_diff_density_rms 0.055 data_1c _database_code_depnum_ccdc_archive 'CCDC 677795' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '2(C19H16O3S3) 0.60(C3H6O1)' _chemical_formula_sum 'C39.80 H35.60 O6.60 S6' _chemical_formula_weight 811.84 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 8.032(4) _cell_length_b 10.645(5) _cell_length_c 12.144(6) _cell_angle_alpha 95.345(6) _cell_angle_beta 107.251(6) _cell_angle_gamma 95.810(6) _cell_volume 978.2(8) _cell_formula_units_Z 1 _cell_measurement_temperature 125(2) _cell_measurement_reflns_used 4120 _cell_measurement_theta_min 2.68 _cell_measurement_theta_max 25.93 _exptl_crystal_description plate _exptl_crystal_colour 'pale yellow' _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.378 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 423 _exptl_absorpt_coefficient_mu 0.397 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9107 _exptl_absorpt_correction_T_max 0.9539 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 125(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 'Bruker SMART 1000 CCD' _diffrn_measurement_method '/w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10967 _diffrn_reflns_av_R_equivalents 0.0428 _diffrn_reflns_av_sigmaI/netI 0.0513 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.68 _diffrn_reflns_theta_max 26.37 _reflns_number_total 3978 _reflns_number_gt 3134 _reflns_threshold_expression >2sigma(I) _computing_data_collection SMART _computing_cell_refinement 'SAINT (Bruker 2001)' _computing_data_reduction 'SAINT (Bruker 2001)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _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^)+(0.0212P)^2^+2.2897P] 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 3978 _refine_ls_number_parameters 284 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0791 _refine_ls_R_factor_gt 0.0594 _refine_ls_wR_factor_ref 0.1267 _refine_ls_wR_factor_gt 0.1206 _refine_ls_goodness_of_fit_ref 1.149 _refine_ls_restrained_S_all 1.149 _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 S1 S 0.25448(11) 0.54137(8) 0.49040(8) 0.0214(2) Uani 1 1 d . . . S2 S 0.91472(11) 0.82807(8) 0.34117(8) 0.0235(2) Uani 1 1 d . . . S3 S 0.07835(13) 0.80599(9) 0.00349(9) 0.0352(3) Uani 1 1 d . . . O1 O 0.4412(3) 0.5363(2) 0.7413(2) 0.0309(6) Uani 1 1 d . . . O2 O 1.1417(3) 1.0667(2) 0.3544(2) 0.0295(6) Uani 1 1 d . . . O3 O 0.0241(4) 0.5776(3) -0.1668(2) 0.0474(8) Uani 1 1 d . . . C1 C 0.4072(4) 0.8276(3) 0.3292(3) 0.0187(7) Uani 1 1 d . . . H1A H 0.3719 0.9084 0.3586 0.022 Uiso 1 1 calc R . . C2 C 0.3778(4) 0.7291(3) 0.4067(3) 0.0180(7) Uani 1 1 d . . . C3 C 0.4792(4) 0.7402(3) 0.5249(3) 0.0181(7) Uani 1 1 d . . . H3A H 0.5735 0.8065 0.5612 0.022 Uiso 1 1 calc R . . C4 C 0.4281(4) 0.6462(3) 0.5820(3) 0.0191(7) Uani 1 1 d . . . C5 C 0.2518(4) 0.6254(3) 0.3769(3) 0.0215(7) Uani 1 1 d . . . C6 C 0.4990(4) 0.6269(3) 0.7036(3) 0.0249(8) Uani 1 1 d . . . C7 C 0.6487(6) 0.7211(4) 0.7800(4) 0.0504(13) Uani 1 1 d . . . H7A H 0.6399 0.7314 0.8590 0.076 Uiso 1 1 calc R . . H7B H 0.6444 0.8032 0.7497 0.076 Uiso 1 1 calc R . . H7C H 0.7602 0.6902 0.7815 0.076 Uiso 1 1 calc R . . C8 C 0.6004(4) 0.8557(3) 0.3377(3) 0.0181(7) Uani 1 1 d . . . C9 C 0.6881(4) 0.9787(3) 0.3449(3) 0.0195(7) Uani 1 1 d . . . C10 C 0.8603(4) 0.9798(3) 0.3472(3) 0.0186(7) Uani 1 1 d . . . C11 C 0.7081(4) 0.7653(3) 0.3355(3) 0.0209(7) Uani 1 1 d . . . C12 C 0.9942(4) 1.0865(3) 0.3532(3) 0.0222(7) Uani 1 1 d . . . C13 C 0.9436(5) 1.2173(3) 0.3547(4) 0.0345(9) Uani 1 1 d . . . H13A H 1.0491 1.2798 0.3718 0.052 Uiso 1 1 calc R . . H13B H 0.8862 1.2320 0.4147 0.052 Uiso 1 1 calc R . . H13C H 0.8621 1.2260 0.2786 0.052 Uiso 1 1 calc R . . C14 C 0.2955(4) 0.7924(3) 0.2030(3) 0.0203(7) Uani 1 1 d . . . C15 C 0.2968(4) 0.6798(3) 0.1307(3) 0.0220(7) Uani 1 1 d . . . H15A H 0.3681 0.6158 0.1565 0.026 Uiso 1 1 calc R . . C16 C 0.1847(4) 0.6732(3) 0.0199(3) 0.0246(8) Uani 1 1 d . . . C17 C 0.1838(4) 0.8690(4) 0.1450(3) 0.0262(8) Uani 1 1 d . . . C18 C 0.1399(5) 0.5706(4) -0.0776(3) 0.0295(9) Uani 1 1 d . . . C19 C 0.2386(5) 0.4593(4) -0.0646(3) 0.0363(9) Uani 1 1 d . . . H19A H 0.1599 0.3823 -0.1071 0.054 Uiso 1 1 calc R . . H19B H 0.2838 0.4492 0.0179 0.054 Uiso 1 1 calc R . . H19C H 0.3371 0.4730 -0.0962 0.054 Uiso 1 1 calc R . . H5 H 0.172(5) 0.599(4) 0.309(3) 0.026(10) Uiso 1 1 d . . . H9 H 0.635(4) 1.048(3) 0.347(3) 0.013(8) Uiso 1 1 d . . . H11 H 0.683(5) 0.678(4) 0.337(3) 0.023(9) Uiso 1 1 d . . . H17 H 0.162(5) 0.946(4) 0.171(3) 0.029(11) Uiso 1 1 d . . . C51 C 0.420(2) 1.0571(18) 0.9656(18) 0.042(4) Uani 0.30 1 d P A -1 H51A H 0.3294 1.0687 0.8942 0.064 Uiso 0.30 1 calc PR A -1 H51B H 0.5212 1.1231 0.9809 0.064 Uiso 0.30 1 calc PR A -1 H51C H 0.3718 1.0635 1.0310 0.064 Uiso 0.30 1 calc PR A -1 C50 C 0.478(2) 0.9267(15) 0.9514(13) 0.041(3) Uani 0.30 1 d P A -1 O50 O 0.4016(16) 0.8498(12) 0.8683(10) 0.061(3) Uani 0.30 1 d P A -1 C52 C 0.637(3) 0.893(2) 1.0460(17) 0.051(5) Uani 0.30 1 d P A -1 H52A H 0.6066 0.8855 1.1177 0.077 Uiso 0.30 1 calc PR A -1 H52B H 0.7375 0.9593 1.0610 0.077 Uiso 0.30 1 calc PR A -1 H52C H 0.6685 0.8111 1.0192 0.077 Uiso 0.30 1 calc PR A -1 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 0.0157(4) 0.0162(4) 0.0282(5) -0.0026(3) 0.0045(3) -0.0048(3) S2 0.0144(4) 0.0186(4) 0.0353(5) 0.0009(4) 0.0058(4) 0.0002(3) S3 0.0284(5) 0.0323(5) 0.0299(5) 0.0055(4) -0.0121(4) -0.0018(4) O1 0.0298(14) 0.0265(14) 0.0335(15) 0.0086(11) 0.0060(12) -0.0032(11) O2 0.0167(12) 0.0257(13) 0.0396(16) -0.0042(11) 0.0052(11) -0.0080(10) O3 0.0488(18) 0.0404(17) 0.0308(16) 0.0020(13) -0.0152(14) -0.0095(14) C1 0.0155(16) 0.0166(16) 0.0192(17) -0.0025(13) -0.0001(13) 0.0014(12) C2 0.0114(15) 0.0182(16) 0.0217(17) -0.0031(13) 0.0033(13) 0.0003(12) C3 0.0115(15) 0.0162(16) 0.0227(17) -0.0017(13) 0.0009(13) 0.0012(12) C4 0.0095(14) 0.0159(16) 0.0273(18) -0.0025(13) 0.0017(13) -0.0017(12) C5 0.0144(16) 0.0206(17) 0.0255(19) -0.0037(14) 0.0036(14) -0.0020(13) C6 0.0190(17) 0.0208(18) 0.031(2) 0.0037(15) 0.0025(15) 0.0020(14) C7 0.041(3) 0.056(3) 0.031(2) 0.014(2) -0.0161(19) -0.024(2) C8 0.0151(15) 0.0183(16) 0.0157(16) 0.0001(13) -0.0013(12) -0.0005(13) C9 0.0143(16) 0.0196(17) 0.0201(17) 0.0006(13) -0.0004(13) 0.0007(13) C10 0.0171(16) 0.0159(16) 0.0191(17) 0.0012(13) 0.0008(13) 0.0009(13) C11 0.0147(16) 0.0170(17) 0.0277(19) 0.0016(14) 0.0032(14) -0.0021(13) C12 0.0168(17) 0.0222(17) 0.0211(18) -0.0036(14) 0.0000(14) -0.0036(13) C13 0.032(2) 0.0216(19) 0.045(2) 0.0021(17) 0.0087(18) -0.0047(16) C14 0.0098(15) 0.0245(18) 0.0223(18) 0.0043(14) -0.0002(13) -0.0032(13) C15 0.0125(15) 0.0240(18) 0.0252(18) 0.0011(14) 0.0018(13) -0.0035(13) C16 0.0173(17) 0.0279(19) 0.0222(18) 0.0043(15) -0.0006(14) -0.0071(14) C17 0.0166(17) 0.026(2) 0.029(2) 0.0035(16) -0.0015(15) -0.0023(15) C18 0.0258(19) 0.033(2) 0.0225(19) 0.0040(15) 0.0017(15) -0.0132(16) C19 0.036(2) 0.040(2) 0.027(2) -0.0049(17) 0.0066(17) -0.0022(18) C51 0.033(11) 0.052(12) 0.049(12) -0.003(9) 0.027(10) 0.003(8) C50 0.048(9) 0.052(10) 0.021(8) 0.007(7) 0.011(7) 0.000(7) O50 0.060(7) 0.068(8) 0.047(7) -0.004(6) 0.008(6) 0.012(6) C52 0.036(11) 0.080(17) 0.036(9) 0.003(10) 0.007(8) 0.018(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 S1 C5 1.707(4) . ? S1 C4 1.721(3) . ? S2 C11 1.705(3) . ? S2 C10 1.716(3) . ? S3 C17 1.711(4) . ? S3 C16 1.722(4) . ? O1 C6 1.214(4) . ? O2 C12 1.220(4) . ? O3 C18 1.214(4) . ? C1 C14 1.518(4) . ? C1 C2 1.518(5) . ? C1 C8 1.521(5) . ? C1 H1A 1.0000 . ? C2 C5 1.363(5) . ? C2 C3 1.412(4) . ? C3 C4 1.366(5) . ? C3 H3A 0.9500 . ? C4 C6 1.458(5) . ? C5 H5 0.88(4) . ? C6 C7 1.495(5) . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C8 C11 1.361(5) . ? C8 C9 1.405(5) . ? C9 C10 1.374(5) . ? C9 H9 0.90(3) . ? C10 C12 1.464(5) . ? C11 H11 0.93(4) . ? C12 C13 1.489(5) . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C14 C17 1.359(5) . ? C14 C15 1.421(5) . ? C15 C16 1.370(5) . ? C15 H15A 0.9500 . ? C16 C18 1.466(5) . ? C17 H17 0.90(4) . ? C18 C19 1.486(6) . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? C51 C50 1.52(2) . ? C51 H51A 0.9800 . ? C51 H51B 0.9800 . ? C51 H51C 0.9800 . ? C50 O50 1.201(18) . ? C50 C52 1.55(2) . ? C52 H52A 0.9800 . ? C52 H52B 0.9800 . ? C52 H52C 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 C5 S1 C4 91.19(17) . . ? C11 S2 C10 91.49(17) . . ? C17 S3 C16 91.77(18) . . ? C14 C1 C2 113.4(3) . . ? C14 C1 C8 110.2(3) . . ? C2 C1 C8 111.7(3) . . ? C14 C1 H1A 107.1 . . ? C2 C1 H1A 107.1 . . ? C8 C1 H1A 107.1 . . ? C5 C2 C3 111.3(3) . . ? C5 C2 C1 126.9(3) . . ? C3 C2 C1 121.7(3) . . ? C4 C3 C2 113.3(3) . . ? C4 C3 H3A 123.3 . . ? C2 C3 H3A 123.3 . . ? C3 C4 C6 129.1(3) . . ? C3 C4 S1 111.2(2) . . ? C6 C4 S1 119.7(2) . . ? C2 C5 S1 112.9(3) . . ? C2 C5 H5 129(2) . . ? S1 C5 H5 119(2) . . ? O1 C6 C4 121.4(3) . . ? O1 C6 C7 120.8(3) . . ? C4 C6 C7 117.7(3) . . ? C6 C7 H7A 109.5 . . ? C6 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C6 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C11 C8 C9 111.7(3) . . ? C11 C8 C1 124.5(3) . . ? C9 C8 C1 123.8(3) . . ? C10 C9 C8 113.2(3) . . ? C10 C9 H9 124(2) . . ? C8 C9 H9 122(2) . . ? C9 C10 C12 130.3(3) . . ? C9 C10 S2 110.9(2) . . ? C12 C10 S2 118.9(3) . . ? C8 C11 S2 112.7(3) . . ? C8 C11 H11 127(2) . . ? S2 C11 H11 120(2) . . ? O2 C12 C10 120.0(3) . . ? O2 C12 C13 121.8(3) . . ? C10 C12 C13 118.3(3) . . ? C12 C13 H13A 109.5 . . ? C12 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C12 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C17 C14 C15 111.9(3) . . ? C17 C14 C1 122.8(3) . . ? C15 C14 C1 125.3(3) . . ? C16 C15 C14 113.1(3) . . ? C16 C15 H15A 123.5 . . ? C14 C15 H15A 123.5 . . ? C15 C16 C18 129.9(3) . . ? C15 C16 S3 110.9(3) . . ? C18 C16 S3 119.1(3) . . ? C14 C17 S3 112.4(3) . . ? C14 C17 H17 129(3) . . ? S3 C17 H17 119(2) . . ? O3 C18 C16 120.1(4) . . ? O3 C18 C19 121.2(4) . . ? C16 C18 C19 118.7(3) . . ? C18 C19 H19A 109.5 . . ? C18 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C18 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? O50 C50 C51 121.1(16) . . ? O50 C50 C52 119.6(16) . . ? C51 C50 C52 119.3(18) . . ? 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 C14 C1 C2 C5 -8.0(5) . . . . ? C8 C1 C2 C5 -133.2(3) . . . . ? C14 C1 C2 C3 175.1(3) . . . . ? C8 C1 C2 C3 49.9(4) . . . . ? C5 C2 C3 C4 -0.3(4) . . . . ? C1 C2 C3 C4 177.0(3) . . . . ? C2 C3 C4 C6 -179.2(3) . . . . ? C2 C3 C4 S1 0.4(4) . . . . ? C5 S1 C4 C3 -0.3(3) . . . . ? C5 S1 C4 C6 179.3(3) . . . . ? C3 C2 C5 S1 0.1(4) . . . . ? C1 C2 C5 S1 -177.0(3) . . . . ? C4 S1 C5 C2 0.1(3) . . . . ? C3 C4 C6 O1 -178.5(3) . . . . ? S1 C4 C6 O1 2.0(5) . . . . ? C3 C4 C6 C7 0.0(6) . . . . ? S1 C4 C6 C7 -179.5(3) . . . . ? C14 C1 C8 C11 -82.0(4) . . . . ? C2 C1 C8 C11 45.0(4) . . . . ? C14 C1 C8 C9 95.8(4) . . . . ? C2 C1 C8 C9 -137.2(3) . . . . ? C11 C8 C9 C10 0.5(4) . . . . ? C1 C8 C9 C10 -177.6(3) . . . . ? C8 C9 C10 C12 179.4(3) . . . . ? C8 C9 C10 S2 -0.3(4) . . . . ? C11 S2 C10 C9 0.1(3) . . . . ? C11 S2 C10 C12 -179.7(3) . . . . ? C9 C8 C11 S2 -0.4(4) . . . . ? C1 C8 C11 S2 177.6(3) . . . . ? C10 S2 C11 C8 0.2(3) . . . . ? C9 C10 C12 O2 180.0(3) . . . . ? S2 C10 C12 O2 -0.4(4) . . . . ? C9 C10 C12 C13 -1.5(5) . . . . ? S2 C10 C12 C13 178.2(3) . . . . ? C2 C1 C14 C17 123.4(4) . . . . ? C8 C1 C14 C17 -110.5(4) . . . . ? C2 C1 C14 C15 -58.3(4) . . . . ? C8 C1 C14 C15 67.7(4) . . . . ? C17 C14 C15 C16 -0.7(4) . . . . ? C1 C14 C15 C16 -179.1(3) . . . . ? C14 C15 C16 C18 -175.7(3) . . . . ? C14 C15 C16 S3 0.6(4) . . . . ? C17 S3 C16 C15 -0.3(3) . . . . ? C17 S3 C16 C18 176.5(3) . . . . ? C15 C14 C17 S3 0.4(4) . . . . ? C1 C14 C17 S3 178.9(3) . . . . ? C16 S3 C17 C14 -0.1(3) . . . . ? C15 C16 C18 O3 173.0(4) . . . . ? S3 C16 C18 O3 -3.0(5) . . . . ? C15 C16 C18 C19 -6.9(6) . . . . ? S3 C16 C18 C19 177.1(3) . . . . ? H1A C1 C2 C5 109.9 . . . . ? H1A C1 C8 C11 161.9 . . . . ? H1A C1 C14 C17 5.6 . . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 26.37 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.596 _refine_diff_density_min -0.574 _refine_diff_density_rms 0.075 data_1d _database_code_depnum_ccdc_archive 'CCDC 677796' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '2(C19H16O3S3) 0.40(C3H6O1)' _chemical_formula_sum 'C39.20 H34.40 O6.40 S6' _chemical_formula_weight 800.23 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 7.990(3) _cell_length_b 10.661(4) _cell_length_c 12.050(4) _cell_angle_alpha 95.542(5) _cell_angle_beta 106.816(4) _cell_angle_gamma 95.760(5) _cell_volume 969.0(6) _cell_formula_units_Z 1 _cell_measurement_temperature 125(2) _cell_measurement_reflns_used 5230 _cell_measurement_theta_min 2.69 _cell_measurement_theta_max 24.88 _exptl_crystal_description plate _exptl_crystal_colour 'pale yellow' _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.371 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 417 _exptl_absorpt_coefficient_mu 0.400 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8828 _exptl_absorpt_correction_T_max 0.9687 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 125(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 'Bruker SMART 1000 CCD' _diffrn_measurement_method '/w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9744 _diffrn_reflns_av_R_equivalents 0.0609 _diffrn_reflns_av_sigmaI/netI 0.0778 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.69 _diffrn_reflns_theta_max 25.02 _reflns_number_total 3417 _reflns_number_gt 2328 _reflns_threshold_expression >2sigma(I) _computing_data_collection SMART _computing_cell_refinement 'SAINT (Bruker 2001)' _computing_data_reduction 'SAINT (Bruker 2001)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _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^)+(0.0314P)^2^+2.2230P] 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 3417 _refine_ls_number_parameters 264 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0999 _refine_ls_R_factor_gt 0.0590 _refine_ls_wR_factor_ref 0.1310 _refine_ls_wR_factor_gt 0.1192 _refine_ls_goodness_of_fit_ref 1.102 _refine_ls_restrained_S_all 1.102 _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 O1 O 0.0591(4) 0.9626(3) -0.2430(3) 0.0313(8) Uani 1 1 d . . . O2 O -0.6435(4) 0.4334(3) 0.1465(3) 0.0296(8) Uani 1 1 d . . . O3 O 0.4758(5) 0.9240(3) 0.6684(3) 0.0458(10) Uani 1 1 d . . . S1 S 0.24484(14) 0.95850(10) 0.00867(10) 0.0215(3) Uani 1 1 d . . . S2 S -0.41777(14) 0.67194(10) 0.15872(10) 0.0232(3) Uani 1 1 d . . . S3 S 0.41758(16) 0.69395(12) 0.49887(11) 0.0344(3) Uani 1 1 d . . . C1 C 0.0920(5) 0.6723(4) 0.1713(4) 0.0180(9) Uani 1 1 d . . . H1A H 0.1281 0.5916 0.1418 0.022 Uiso 1 1 calc R . . C2 C 0.1212(5) 0.7712(4) 0.0925(4) 0.0161(9) Uani 1 1 d . . . C3 C 0.0214(5) 0.7592(4) -0.0265(4) 0.0179(10) Uani 1 1 d . . . C4 C 0.0728(5) 0.8529(4) -0.0831(4) 0.0187(10) Uani 1 1 d . . . C5 C 0.2482(5) 0.8754(4) 0.1228(4) 0.0216(10) Uani 1 1 d . . . C6 C 0.0024(5) 0.8725(4) -0.2053(4) 0.0224(10) Uani 1 1 d . . . C7 C -0.1443(7) 0.7770(5) -0.2830(5) 0.0518(17) Uani 1 1 d . . . H7A H -0.2574 0.8083 -0.2890 0.078 Uiso 1 1 calc R . . H7B H -0.1427 0.6964 -0.2501 0.078 Uiso 1 1 calc R . . H7C H -0.1291 0.7636 -0.3609 0.078 Uiso 1 1 calc R . . C8 C -0.1015(5) 0.6447(4) 0.1626(3) 0.0174(9) Uani 1 1 d . . . C9 C -0.1886(5) 0.5220(4) 0.1562(3) 0.0193(10) Uani 1 1 d . . . H9A H -0.1337 0.4472 0.1535 0.023 Uiso 1 1 calc R . . C10 C -0.3610(5) 0.5211(4) 0.1543(4) 0.0196(10) Uani 1 1 d . . . C11 C -0.2101(5) 0.7346(4) 0.1639(4) 0.0211(10) Uani 1 1 d . . . C12 C -0.4953(5) 0.4145(4) 0.1483(4) 0.0230(10) Uani 1 1 d . . . C13 C -0.4422(6) 0.2835(4) 0.1475(5) 0.0345(12) Uani 1 1 d . . . H13A H -0.3573 0.2768 0.2231 0.052 Uiso 1 1 calc R . . H13B H -0.3879 0.2675 0.0852 0.052 Uiso 1 1 calc R . . H13C H -0.5467 0.2206 0.1337 0.052 Uiso 1 1 calc R . . C14 C 0.2029(5) 0.7086(4) 0.2977(4) 0.0193(10) Uani 1 1 d . . . C15 C 0.2028(5) 0.8213(4) 0.3696(4) 0.0212(10) Uani 1 1 d . . . H15A H 0.1337 0.8863 0.3433 0.025 Uiso 1 1 calc R . . C16 C 0.3132(5) 0.8269(4) 0.4815(4) 0.0241(11) Uani 1 1 d . . . C17 C 0.3119(6) 0.6317(5) 0.3576(4) 0.0279(11) Uani 1 1 d . . . C18 C 0.3599(6) 0.9315(4) 0.5789(4) 0.0279(11) Uani 1 1 d . . . C19 C 0.2656(6) 1.0434(5) 0.5650(4) 0.0351(12) Uani 1 1 d . . . H19A H 0.1718 1.0355 0.6024 0.053 Uiso 1 1 calc R . . H19B H 0.2137 1.0489 0.4816 0.053 Uiso 1 1 calc R . . H19C H 0.3485 1.1205 0.6019 0.053 Uiso 1 1 calc R . . H3 H -0.071(6) 0.692(4) -0.056(4) 0.026(12) Uiso 1 1 d . . . H8 H 0.335(6) 0.901(4) 0.196(4) 0.025(12) Uiso 1 1 d . . . H11 H -0.181(5) 0.822(4) 0.167(3) 0.014(11) Uiso 1 1 d . . . H17 H 0.341(5) 0.554(4) 0.330(3) 0.011(10) Uiso 1 1 d . . . O50 O 1.094(3) 0.6492(19) 0.6317(18) 0.059(6) Uiso 0.20 1 d P A -1 C50 C 1.020(4) 0.571(3) 0.548(3) 0.044(7) Uiso 0.20 1 d P A -1 C51 C 0.865(4) 0.606(3) 0.451(3) 0.061(9) Uiso 0.20 1 d P A -1 H51A H 0.8758 0.6988 0.4524 0.092 Uiso 0.20 1 calc PR A -1 H51B H 0.7531 0.5757 0.4642 0.092 Uiso 0.20 1 calc PR A -1 H51C H 0.8665 0.5665 0.3745 0.092 Uiso 0.20 1 calc PR A -1 C52 C 1.083(4) 0.447(3) 0.532(3) 0.052(8) Uiso 0.20 1 d P A -1 H52A H 1.1833 0.4405 0.5998 0.078 Uiso 0.20 1 calc PR A -1 H52B H 1.1195 0.4403 0.4610 0.078 Uiso 0.20 1 calc PR A -1 H52C H 0.9874 0.3788 0.5247 0.078 Uiso 0.20 1 calc PR A -1 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0325(18) 0.0282(19) 0.031(2) 0.0104(15) 0.0071(15) -0.0048(15) O2 0.0156(16) 0.0282(18) 0.039(2) -0.0028(15) 0.0053(14) -0.0100(13) O3 0.049(2) 0.041(2) 0.026(2) 0.0039(17) -0.0170(17) -0.0075(17) S1 0.0167(5) 0.0177(6) 0.0268(7) -0.0004(5) 0.0048(5) -0.0049(4) S2 0.0155(5) 0.0196(6) 0.0331(7) 0.0022(5) 0.0064(5) 0.0003(4) S3 0.0287(7) 0.0318(7) 0.0286(7) 0.0059(6) -0.0117(5) -0.0021(5) C1 0.017(2) 0.018(2) 0.016(2) 0.0019(18) 0.0010(18) 0.0040(17) C2 0.012(2) 0.016(2) 0.019(2) 0.0011(18) 0.0031(17) -0.0008(16) C3 0.010(2) 0.014(2) 0.025(3) 0.0001(19) 0.0002(18) -0.0002(18) C4 0.013(2) 0.018(2) 0.024(2) -0.0011(19) 0.0051(18) 0.0006(17) C5 0.014(2) 0.024(2) 0.022(3) -0.004(2) 0.002(2) -0.0026(18) C6 0.015(2) 0.023(3) 0.026(3) 0.005(2) 0.0019(19) -0.0001(18) C7 0.046(3) 0.056(4) 0.032(3) 0.018(3) -0.014(3) -0.028(3) C8 0.013(2) 0.021(2) 0.011(2) 0.0003(18) -0.0053(17) -0.0018(18) C9 0.015(2) 0.022(2) 0.015(2) 0.0006(18) -0.0027(17) 0.0012(18) C10 0.018(2) 0.019(2) 0.018(2) 0.0018(18) 0.0012(18) -0.0033(18) C11 0.017(2) 0.016(2) 0.027(3) 0.0013(19) 0.0040(19) -0.0030(19) C12 0.016(2) 0.025(3) 0.023(3) -0.0013(19) 0.0013(19) -0.0053(19) C13 0.033(3) 0.020(3) 0.049(3) 0.002(2) 0.014(2) -0.007(2) C14 0.0087(19) 0.022(2) 0.023(2) 0.0020(19) 0.0008(17) -0.0034(17) C15 0.012(2) 0.024(2) 0.023(3) 0.004(2) 0.0007(18) -0.0047(18) C16 0.019(2) 0.026(3) 0.021(3) -0.001(2) 0.0015(19) -0.0081(19) C17 0.022(2) 0.022(3) 0.032(3) -0.001(2) 0.000(2) -0.005(2) C18 0.025(2) 0.033(3) 0.021(3) 0.005(2) 0.003(2) -0.012(2) C19 0.034(3) 0.041(3) 0.026(3) -0.006(2) 0.008(2) -0.003(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 O1 C6 1.205(5) . ? O2 C12 1.216(5) . ? O3 C18 1.217(5) . ? S1 C5 1.701(5) . ? S1 C4 1.718(4) . ? S2 C11 1.706(4) . ? S2 C10 1.714(4) . ? S3 C17 1.700(5) . ? S3 C16 1.715(5) . ? C1 C14 1.515(6) . ? C1 C8 1.515(6) . ? C1 C2 1.529(6) . ? C1 H1A 1.0000 . ? C2 C5 1.371(6) . ? C2 C3 1.411(6) . ? C3 C4 1.358(6) . ? C3 H3 0.94(4) . ? C4 C6 1.460(6) . ? C5 H8 0.94(4) . ? C6 C7 1.493(6) . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C8 C11 1.358(6) . ? C8 C9 1.403(6) . ? C9 C10 1.370(6) . ? C9 H9A 0.9500 . ? C10 C12 1.464(6) . ? C11 H11 0.93(4) . ? C12 C13 1.500(6) . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C14 C17 1.358(6) . ? C14 C15 1.412(6) . ? C15 C16 1.373(6) . ? C15 H15A 0.9500 . ? C16 C18 1.473(6) . ? C17 H17 0.94(4) . ? C18 C19 1.472(7) . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? O50 C50 1.21(3) . ? C50 C52 1.47(4) . ? C50 C51 1.55(4) . ? C51 H51A 0.9800 . ? C51 H51B 0.9800 . ? C51 H51C 0.9800 . ? C52 H52A 0.9800 . ? C52 H52B 0.9800 . ? C52 H52C 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 C5 S1 C4 91.4(2) . . ? C11 S2 C10 91.1(2) . . ? C17 S3 C16 91.1(2) . . ? C14 C1 C8 110.4(3) . . ? C14 C1 C2 113.2(3) . . ? C8 C1 C2 111.1(3) . . ? C14 C1 H1A 107.2 . . ? C8 C1 H1A 107.2 . . ? C2 C1 H1A 107.2 . . ? C5 C2 C3 111.5(4) . . ? C5 C2 C1 126.5(4) . . ? C3 C2 C1 121.9(3) . . ? C4 C3 C2 113.1(4) . . ? C4 C3 H3 129(3) . . ? C2 C3 H3 118(3) . . ? C3 C4 C6 129.1(4) . . ? C3 C4 S1 111.6(3) . . ? C6 C4 S1 119.3(3) . . ? C2 C5 S1 112.5(3) . . ? C2 C5 H8 128(3) . . ? S1 C5 H8 120(3) . . ? O1 C6 C4 121.7(4) . . ? O1 C6 C7 120.5(4) . . ? C4 C6 C7 117.8(4) . . ? C6 C7 H7A 109.5 . . ? C6 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C6 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C11 C8 C9 111.7(4) . . ? C11 C8 C1 124.7(4) . . ? C9 C8 C1 123.6(4) . . ? C10 C9 C8 113.1(4) . . ? C10 C9 H9A 123.5 . . ? C8 C9 H9A 123.5 . . ? C9 C10 C12 130.2(4) . . ? C9 C10 S2 111.3(3) . . ? C12 C10 S2 118.5(3) . . ? C8 C11 S2 112.9(3) . . ? C8 C11 H11 126(2) . . ? S2 C11 H11 121(2) . . ? O2 C12 C10 120.3(4) . . ? O2 C12 C13 121.9(4) . . ? C10 C12 C13 117.8(4) . . ? C12 C13 H13A 109.5 . . ? C12 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C12 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C17 C14 C15 111.4(4) . . ? C17 C14 C1 122.9(4) . . ? C15 C14 C1 125.6(4) . . ? C16 C15 C14 112.7(4) . . ? C16 C15 H15A 123.6 . . ? C14 C15 H15A 123.6 . . ? C15 C16 C18 129.3(4) . . ? C15 C16 S3 111.4(3) . . ? C18 C16 S3 119.2(3) . . ? C14 C17 S3 113.3(4) . . ? C14 C17 H17 129(2) . . ? S3 C17 H17 117(2) . . ? O3 C18 C19 121.5(4) . . ? O3 C18 C16 119.5(5) . . ? C19 C18 C16 119.0(4) . . ? C18 C19 H19A 109.5 . . ? C18 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C18 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? O50 C50 C52 121(3) . . ? O50 C50 C51 119(3) . . ? C52 C50 C51 119(3) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C14 C1 C2 C5 8.5(6) . . . . ? C8 C1 C2 C5 133.5(4) . . . . ? C14 C1 C2 C3 -175.6(4) . . . . ? C8 C1 C2 C3 -50.6(5) . . . . ? C5 C2 C3 C4 -0.3(5) . . . . ? C1 C2 C3 C4 -176.8(4) . . . . ? C2 C3 C4 C6 179.9(4) . . . . ? C2 C3 C4 S1 -0.1(5) . . . . ? C5 S1 C4 C3 0.4(3) . . . . ? C5 S1 C4 C6 -179.6(3) . . . . ? C3 C2 C5 S1 0.6(5) . . . . ? C1 C2 C5 S1 177.0(3) . . . . ? C4 S1 C5 C2 -0.6(3) . . . . ? C3 C4 C6 O1 178.2(4) . . . . ? S1 C4 C6 O1 -1.8(6) . . . . ? C3 C4 C6 C7 -1.4(7) . . . . ? S1 C4 C6 C7 178.6(4) . . . . ? C14 C1 C8 C11 82.0(5) . . . . ? C2 C1 C8 C11 -44.5(5) . . . . ? C14 C1 C8 C9 -95.7(5) . . . . ? C2 C1 C8 C9 137.8(4) . . . . ? C11 C8 C9 C10 -0.8(5) . . . . ? C1 C8 C9 C10 177.2(4) . . . . ? C8 C9 C10 C12 -179.9(4) . . . . ? C8 C9 C10 S2 0.7(5) . . . . ? C11 S2 C10 C9 -0.3(3) . . . . ? C11 S2 C10 C12 -179.8(4) . . . . ? C9 C8 C11 S2 0.5(5) . . . . ? C1 C8 C11 S2 -177.4(3) . . . . ? C10 S2 C11 C8 -0.1(4) . . . . ? C9 C10 C12 O2 -179.4(4) . . . . ? S2 C10 C12 O2 0.0(6) . . . . ? C9 C10 C12 C13 2.1(7) . . . . ? S2 C10 C12 C13 -178.5(3) . . . . ? C8 C1 C14 C17 109.1(5) . . . . ? C2 C1 C14 C17 -125.6(4) . . . . ? C8 C1 C14 C15 -68.3(5) . . . . ? C2 C1 C14 C15 57.1(5) . . . . ? C17 C14 C15 C16 0.6(5) . . . . ? C1 C14 C15 C16 178.3(4) . . . . ? C14 C15 C16 C18 174.8(4) . . . . ? C14 C15 C16 S3 0.0(5) . . . . ? C17 S3 C16 C15 -0.5(3) . . . . ? C17 S3 C16 C18 -175.9(4) . . . . ? C15 C14 C17 S3 -1.0(5) . . . . ? C1 C14 C17 S3 -178.7(3) . . . . ? C16 S3 C17 C14 0.9(4) . . . . ? C15 C16 C18 O3 -171.9(4) . . . . ? S3 C16 C18 O3 2.5(6) . . . . ? C15 C16 C18 C19 7.7(7) . . . . ? S3 C16 C18 C19 -177.9(3) . . . . ? H1A C1 C2 C5 -109.6 . . . . ? H1A C1 C8 C11 -161.4 . . . . ? H1A C1 C14 C17 -7.5 . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.02 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.358 _refine_diff_density_min -0.351 _refine_diff_density_rms 0.078 data_1e _database_code_depnum_ccdc_archive 'CCDC 677797' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '2(C19H16O3S3) 0.24(C3H6O1)' _chemical_formula_sum 'C38.72 H33.44 O6.24 S6' _chemical_formula_weight 790.93 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 7.9572(17) _cell_length_b 10.694(2) _cell_length_c 11.958(3) _cell_angle_alpha 95.691(3) _cell_angle_beta 106.430(3) _cell_angle_gamma 95.669(3) _cell_volume 962.6(4) _cell_formula_units_Z 1 _cell_measurement_temperature 125(2) _cell_measurement_reflns_used 2743 _cell_measurement_theta_min 1.79 _cell_measurement_theta_max 20.85 _exptl_crystal_description plate _exptl_crystal_colour 'pale yellow' _exptl_crystal_size_max 0.14 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.364 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 412 _exptl_absorpt_coefficient_mu 0.401 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9460 _exptl_absorpt_correction_T_max 0.9686 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 125(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 'Bruker SMART 1000 CCD' _diffrn_measurement_method '/w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6589 _diffrn_reflns_av_R_equivalents 0.0472 _diffrn_reflns_av_sigmaI/netI 0.0474 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 1.79 _diffrn_reflns_theta_max 20.85 _reflns_number_total 2018 _reflns_number_gt 1500 _reflns_threshold_expression >2sigma(I) _computing_data_collection SMART _computing_cell_refinement 'SAINT (Bruker 2001)' _computing_data_reduction 'SAINT (Bruker 2001)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _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^)+(0.0213P)^2^+1.1609P] 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 2018 _refine_ls_number_parameters 260 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0598 _refine_ls_R_factor_gt 0.0354 _refine_ls_wR_factor_ref 0.0803 _refine_ls_wR_factor_gt 0.0720 _refine_ls_goodness_of_fit_ref 1.061 _refine_ls_restrained_S_all 1.061 _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 S1 S 1.24437(14) 0.45809(10) 0.00771(9) 0.0268(3) Uani 1 1 d . . . S2 S 0.58017(13) 0.17193(10) 0.15908(10) 0.0289(3) Uani 1 1 d . . . S3 S 1.41395(15) 0.19391(11) 0.50122(10) 0.0369(3) Uani 1 1 d . . . O1 O 1.0587(4) 0.4627(3) -0.2454(2) 0.0350(8) Uani 1 1 d . . . O2 O 0.3545(4) -0.0664(2) 0.1476(2) 0.0330(8) Uani 1 1 d . . . O3 O 1.4757(4) 0.4247(3) 0.6698(3) 0.0477(9) Uani 1 1 d . . . C1 C 1.0919(5) 0.1742(4) 0.1720(3) 0.0204(10) Uani 1 1 d . . . H1 H 1.1283 0.0937 0.1421 0.025 Uiso 1 1 calc R . . C2 C 1.1219(5) 0.2707(3) 0.0930(3) 0.0206(10) Uani 1 1 d . . . C3 C 1.0228(5) 0.2596(4) -0.0262(3) 0.0220(10) Uani 1 1 d . . . H3A H 0.9290 0.1930 -0.0625 0.026 Uiso 1 1 calc R . . C4 C 1.0728(5) 0.3525(4) -0.0853(4) 0.0225(10) Uani 1 1 d . . . C5 C 1.2456(5) 0.3754(4) 0.1222(4) 0.0259(11) Uani 1 1 d . . . C6 C 1.0030(5) 0.3719(4) -0.2076(4) 0.0264(11) Uani 1 1 d . . . C7 C 0.8591(6) 0.2743(4) -0.2865(4) 0.0521(15) Uani 1 1 d . . . H7A H 0.7439 0.3019 -0.2909 0.078 Uiso 1 1 calc R . . H7B H 0.8656 0.1932 -0.2549 0.078 Uiso 1 1 calc R . . H7C H 0.8738 0.2639 -0.3654 0.078 Uiso 1 1 calc R . . C8 C 0.8975(5) 0.1454(4) 0.1632(3) 0.0201(10) Uani 1 1 d . . . C9 C 0.8100(5) 0.0227(4) 0.1580(3) 0.0209(10) Uani 1 1 d . . . H9A H 0.8654 -0.0519 0.1560 0.025 Uiso 1 1 calc R . . C10 C 0.6379(5) 0.0223(4) 0.1561(3) 0.0237(10) Uani 1 1 d . . . C11 C 0.7874(5) 0.2347(4) 0.1638(3) 0.0236(10) Uani 1 1 d . . . C12 C 0.5040(6) -0.0849(4) 0.1500(3) 0.0256(11) Uani 1 1 d . . . C13 C 0.5588(6) -0.2147(4) 0.1502(4) 0.0373(12) Uani 1 1 d . . . H13A H 0.6390 -0.2217 0.2277 0.056 Uiso 1 1 calc R . . H13B H 0.6192 -0.2295 0.0902 0.056 Uiso 1 1 calc R . . H13C H 0.4539 -0.2781 0.1330 0.056 Uiso 1 1 calc R . . C14 C 1.2016(5) 0.2084(4) 0.2988(3) 0.0224(10) Uani 1 1 d . . . C15 C 1.2027(5) 0.3215(4) 0.3713(3) 0.0229(10) Uani 1 1 d . . . H15A H 1.1343 0.3866 0.3447 0.028 Uiso 1 1 calc R . . C16 C 1.3118(5) 0.3281(4) 0.4832(4) 0.0257(11) Uani 1 1 d . . . C17 C 1.3089(6) 0.1319(5) 0.3584(4) 0.0304(11) Uani 1 1 d . . . C18 C 1.3589(6) 0.4323(4) 0.5798(4) 0.0312(11) Uani 1 1 d . . . C19 C 1.2681(6) 0.5458(4) 0.5656(4) 0.0390(12) Uani 1 1 d . . . H19A H 1.1664 0.5364 0.5964 0.058 Uiso 1 1 calc R . . H19B H 1.2274 0.5557 0.4820 0.058 Uiso 1 1 calc R . . H19C H 1.3501 0.6207 0.6090 0.058 Uiso 1 1 calc R . . H5 H 1.327(5) 0.403(3) 0.195(3) 0.020(11) Uiso 1 1 d . . . H17 H 1.340(5) 0.053(4) 0.327(3) 0.028(12) Uiso 1 1 d . . . H19 H 0.819(5) 0.328(4) 0.170(3) 0.036(12) Uiso 1 1 d . . . O50 O 0.081(5) 0.148(4) 0.633(4) 0.108(13) Uiso 0.12 1 d P A -1 C51 C 0.008(6) 0.070(4) 0.541(4) 0.065(14) Uiso 0.12 1 d PD A -1 C52 C -0.141(7) 0.114(5) 0.453(4) 0.078(17) Uiso 0.12 1 d PD A -1 H52A H -0.1630 0.1971 0.4852 0.117 Uiso 0.12 1 calc PR A -1 H52B H -0.2481 0.0532 0.4365 0.117 Uiso 0.12 1 calc PR A -1 H52C H -0.1100 0.1223 0.3803 0.117 Uiso 0.12 1 calc PR A -1 C50 C 0.082(7) -0.052(5) 0.536(5) 0.065(14) Uiso 0.12 1 d PD A -1 H50A H 0.1677 -0.0573 0.6120 0.097 Uiso 0.12 1 calc PR A -1 H50B H 0.1410 -0.0572 0.4743 0.097 Uiso 0.12 1 calc PR A -1 H50C H -0.0137 -0.1231 0.5184 0.097 Uiso 0.12 1 calc PR A -1 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 0.0214(6) 0.0211(6) 0.0348(7) -0.0018(5) 0.0077(5) -0.0051(5) S2 0.0193(6) 0.0232(7) 0.0425(8) 0.0014(5) 0.0086(5) -0.0008(5) S3 0.0309(7) 0.0350(7) 0.0332(8) 0.0051(6) -0.0072(6) -0.0011(6) O1 0.0377(19) 0.0291(18) 0.0375(19) 0.0102(16) 0.0111(15) -0.0048(15) O2 0.0195(19) 0.0304(18) 0.046(2) -0.0032(14) 0.0104(15) -0.0058(14) O3 0.053(2) 0.039(2) 0.032(2) 0.0015(16) -0.0120(18) -0.0102(17) C1 0.014(2) 0.021(2) 0.024(3) 0.000(2) 0.0036(19) -0.0011(18) C2 0.011(2) 0.020(3) 0.030(3) -0.001(2) 0.006(2) 0.0008(19) C3 0.014(2) 0.018(2) 0.029(3) 0.000(2) 0.001(2) -0.0036(18) C4 0.014(2) 0.020(2) 0.031(3) -0.003(2) 0.006(2) -0.0002(19) C5 0.017(2) 0.030(3) 0.027(3) -0.005(2) 0.004(2) -0.001(2) C6 0.020(3) 0.030(3) 0.029(3) 0.007(2) 0.005(2) 0.003(2) C7 0.047(3) 0.053(3) 0.038(3) 0.016(3) -0.010(3) -0.021(3) C8 0.016(2) 0.020(3) 0.020(2) 0.0009(19) 0.0005(19) 0.000(2) C9 0.018(3) 0.021(3) 0.021(2) 0.0036(19) 0.0006(19) 0.005(2) C10 0.022(3) 0.018(2) 0.028(3) 0.0003(19) 0.005(2) 0.000(2) C11 0.018(2) 0.020(3) 0.030(3) 0.000(2) 0.006(2) -0.005(2) C12 0.023(3) 0.025(3) 0.025(3) -0.001(2) 0.004(2) -0.002(2) C13 0.037(3) 0.021(3) 0.052(3) 0.002(2) 0.014(2) -0.007(2) C14 0.013(2) 0.026(3) 0.027(3) 0.004(2) 0.004(2) 0.000(2) C15 0.014(2) 0.027(3) 0.025(3) 0.006(2) 0.003(2) -0.0024(19) C16 0.023(2) 0.025(3) 0.026(3) 0.001(2) 0.005(2) -0.006(2) C17 0.023(3) 0.030(3) 0.031(3) -0.001(2) 0.001(2) -0.003(2) C18 0.027(3) 0.033(3) 0.028(3) 0.005(2) 0.004(2) -0.013(2) C19 0.043(3) 0.036(3) 0.035(3) -0.004(2) 0.012(2) -0.005(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 S1 C5 1.700(4) . ? S1 C4 1.721(4) . ? S2 C11 1.701(4) . ? S2 C10 1.708(4) . ? S3 C17 1.707(4) . ? S3 C16 1.720(4) . ? O1 C6 1.208(4) . ? O2 C12 1.218(4) . ? O3 C18 1.223(5) . ? C1 C14 1.508(5) . ? C1 C2 1.511(5) . ? C1 C8 1.519(5) . ? C1 H1 1.0000 . ? C2 C5 1.362(5) . ? C2 C3 1.407(5) . ? C3 C4 1.366(5) . ? C3 H3A 0.9500 . ? C4 C6 1.454(6) . ? C5 H5 0.93(4) . ? C6 C7 1.500(6) . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C8 C11 1.358(5) . ? C8 C9 1.410(5) . ? C9 C10 1.363(5) . ? C9 H9A 0.9500 . ? C10 C12 1.466(5) . ? C11 H19 0.99(4) . ? C12 C13 1.496(6) . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C14 C17 1.347(6) . ? C14 C15 1.415(5) . ? C15 C16 1.365(5) . ? C15 H15A 0.9500 . ? C16 C18 1.460(6) . ? C17 H17 0.97(4) . ? C18 C19 1.472(6) . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? O50 C51 1.27(5) . ? C51 C50 1.49(4) . ? C51 C52 1.50(4) . ? C52 H52A 0.9800 . ? C52 H52B 0.9800 . ? C52 H52C 0.9800 . ? C50 H50A 0.9800 . ? C50 H50B 0.9800 . ? C50 H50C 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 C5 S1 C4 91.3(2) . . ? C11 S2 C10 91.3(2) . . ? C17 S3 C16 91.0(2) . . ? C14 C1 C2 114.2(3) . . ? C14 C1 C8 110.5(3) . . ? C2 C1 C8 111.6(3) . . ? C14 C1 H1 106.7 . . ? C2 C1 H1 106.7 . . ? C8 C1 H1 106.7 . . ? C5 C2 C3 110.5(4) . . ? C5 C2 C1 127.2(4) . . ? C3 C2 C1 122.4(3) . . ? C4 C3 C2 114.3(3) . . ? C4 C3 H3A 122.8 . . ? C2 C3 H3A 122.8 . . ? C3 C4 C6 130.0(4) . . ? C3 C4 S1 110.4(3) . . ? C6 C4 S1 119.6(3) . . ? C2 C5 S1 113.5(3) . . ? C2 C5 H5 127(2) . . ? S1 C5 H5 120(2) . . ? O1 C6 C4 121.7(4) . . ? O1 C6 C7 120.6(4) . . ? C4 C6 C7 117.7(4) . . ? C6 C7 H7A 109.5 . . ? C6 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C6 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C11 C8 C9 111.4(3) . . ? C11 C8 C1 124.5(3) . . ? C9 C8 C1 124.1(4) . . ? C10 C9 C8 113.0(4) . . ? C10 C9 H9A 123.5 . . ? C8 C9 H9A 123.5 . . ? C9 C10 C12 129.6(4) . . ? C9 C10 S2 111.4(3) . . ? C12 C10 S2 119.0(3) . . ? C8 C11 S2 112.8(3) . . ? C8 C11 H19 126(2) . . ? S2 C11 H19 121(2) . . ? O2 C12 C10 120.1(4) . . ? O2 C12 C13 121.9(4) . . ? C10 C12 C13 118.0(4) . . ? C12 C13 H13A 109.5 . . ? C12 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C12 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C17 C14 C15 111.3(4) . . ? C17 C14 C1 123.5(4) . . ? C15 C14 C1 125.2(4) . . ? C16 C15 C14 113.4(4) . . ? C16 C15 H15A 123.3 . . ? C14 C15 H15A 123.3 . . ? C15 C16 C18 129.6(4) . . ? C15 C16 S3 110.9(3) . . ? C18 C16 S3 119.3(3) . . ? C14 C17 S3 113.4(4) . . ? C14 C17 H17 127(2) . . ? S3 C17 H17 119(2) . . ? O3 C18 C16 119.3(4) . . ? O3 C18 C19 121.3(4) . . ? C16 C18 C19 119.4(4) . . ? C18 C19 H19A 109.5 . . ? C18 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C18 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? O50 C51 C50 116(4) . . ? O50 C51 C52 115(4) . . ? C50 C51 C52 130(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 C14 C1 C2 C5 6.5(6) . . . . ? C8 C1 C2 C5 132.7(4) . . . . ? C14 C1 C2 C3 -175.5(3) . . . . ? C8 C1 C2 C3 -49.3(5) . . . . ? C5 C2 C3 C4 0.9(5) . . . . ? C1 C2 C3 C4 -177.4(3) . . . . ? C2 C3 C4 C6 179.8(4) . . . . ? C2 C3 C4 S1 -0.8(4) . . . . ? C5 S1 C4 C3 0.3(3) . . . . ? C5 S1 C4 C6 179.9(3) . . . . ? C3 C2 C5 S1 -0.6(4) . . . . ? C1 C2 C5 S1 177.5(3) . . . . ? C4 S1 C5 C2 0.2(3) . . . . ? C3 C4 C6 O1 177.2(4) . . . . ? S1 C4 C6 O1 -2.2(5) . . . . ? C3 C4 C6 C7 -3.3(6) . . . . ? S1 C4 C6 C7 177.3(3) . . . . ? C14 C1 C8 C11 83.5(5) . . . . ? C2 C1 C8 C11 -44.7(5) . . . . ? C14 C1 C8 C9 -93.9(4) . . . . ? C2 C1 C8 C9 137.9(4) . . . . ? C11 C8 C9 C10 -0.7(5) . . . . ? C1 C8 C9 C10 177.0(3) . . . . ? C8 C9 C10 C12 179.4(4) . . . . ? C8 C9 C10 S2 0.7(4) . . . . ? C11 S2 C10 C9 -0.4(3) . . . . ? C11 S2 C10 C12 -179.3(3) . . . . ? C9 C8 C11 S2 0.3(4) . . . . ? C1 C8 C11 S2 -177.3(3) . . . . ? C10 S2 C11 C8 0.0(3) . . . . ? C9 C10 C12 O2 -179.0(4) . . . . ? S2 C10 C12 O2 -0.3(5) . . . . ? C9 C10 C12 C13 2.7(6) . . . . ? S2 C10 C12 C13 -178.7(3) . . . . ? C2 C1 C14 C17 -125.1(4) . . . . ? C8 C1 C14 C17 108.1(4) . . . . ? C2 C1 C14 C15 56.7(5) . . . . ? C8 C1 C14 C15 -70.1(5) . . . . ? C17 C14 C15 C16 0.6(5) . . . . ? C1 C14 C15 C16 179.0(3) . . . . ? C14 C15 C16 C18 174.6(4) . . . . ? C14 C15 C16 S3 -0.4(4) . . . . ? C17 S3 C16 C15 0.1(3) . . . . ? C17 S3 C16 C18 -175.5(3) . . . . ? C15 C14 C17 S3 -0.5(5) . . . . ? C1 C14 C17 S3 -178.9(3) . . . . ? C16 S3 C17 C14 0.2(3) . . . . ? C15 C16 C18 O3 -171.5(4) . . . . ? S3 C16 C18 O3 3.2(5) . . . . ? C15 C16 C18 C19 6.9(6) . . . . ? S3 C16 C18 C19 -178.4(3) . . . . ? H1 C1 C2 C5 -111.1 . . . . ? H1 C1 C8 C11 -160.9 . . . . ? H1 C1 C14 C17 -7.5 . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 20.85 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.216 _refine_diff_density_min -0.227 _refine_diff_density_rms 0.049