# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2009 data_global _journal_coden_Cambridge 182 loop_ _publ_author_name 'Jianbo Wang' 'Lingling Peng' 'Wenxiong Zhang' 'Xia Zhao' 'Zhenzhen Zhong' _publ_contact_author_name 'Jianbo Wang' _publ_contact_author_email WANGJB@PKU.EDU.CN _publ_section_title ; Au(PPh3)Cl/AgSbF6-Catalyzed Rearrangement of Propargylic 1,3-Dithianes: Formation of 8-Membered 1,3-Bisthio-Substituted Cyclic Allenes ; # Attachment '2a.cif' data_8305 _database_code_depnum_ccdc_archive 'CCDC 720411' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H16 S2' _chemical_formula_weight 296.43 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 10.491(2) _cell_length_b 8.7754(18) _cell_length_c 17.309(4) _cell_angle_alpha 90.00 _cell_angle_beta 104.25(3) _cell_angle_gamma 90.00 _cell_volume 1544.4(5) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 10549 _cell_measurement_theta_min 2.07 _cell_measurement_theta_max 27.48 _exptl_crystal_description ? _exptl_crystal_colour colorless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.275 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 624 _exptl_absorpt_coefficient_mu 0.332 _exptl_absorpt_correction_type Empirical _exptl_absorpt_correction_T_min 0.8787 _exptl_absorpt_correction_T_max 0.9366 _exptl_absorpt_process_details ; HIGASHI, T. (1995). Abscor-Empirical Absorption Correction based on Fourier Series Approximation. Rigaku Corporation,Tokyo,Japan. ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku RAXIS RAPID IP' _diffrn_measurement_method \W _diffrn_detector_area_resol_mean 10.00 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 10549 _diffrn_reflns_av_R_equivalents 0.03125601 _diffrn_reflns_av_sigmaI/netI 0.0478 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.07 _diffrn_reflns_theta_max 27.48 _reflns_number_total 3511 _reflns_number_gt 2256 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Rapid-AUTO (Rigaku,2000)' _computing_cell_refinement Rapid-AUTO _computing_data_reduction 'CrystalStructure (Rigaku/MSC,2000)' _computing_structure_solution SHELXS-97,(Sheldrick,1997) _computing_structure_refinement SHELXL-97,(Sheldrick,1997) _computing_molecular_graphics 'Siemens SHELXTL V4.2,(Sheldrick,1990)' _computing_publication_material SHELXL-97,(Sheldrick,1997) _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^)+(0.0520P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment none _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3511 _refine_ls_number_parameters 181 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0729 _refine_ls_R_factor_gt 0.0404 _refine_ls_wR_factor_ref 0.1031 _refine_ls_wR_factor_gt 0.0946 _refine_ls_goodness_of_fit_ref 0.994 _refine_ls_restrained_S_all 0.994 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.56534(16) 0.06465(19) 0.30025(10) 0.0369(4) Uani 1 1 d . . . C2 C 0.63002(17) 0.1530(2) 0.35766(11) 0.0409(4) Uani 1 1 d . . . C3 C 0.72520(17) 0.2248(2) 0.40759(10) 0.0411(4) Uani 1 1 d . . . C4 C 0.71369(19) 0.3819(2) 0.43679(11) 0.0447(5) Uani 1 1 d . . . C5 C 0.8189(2) 0.4583(3) 0.48445(14) 0.0664(6) Uani 1 1 d . . . H5 H 0.9000 0.4100 0.5009 0.080 Uiso 1 1 calc R . . C6 C 0.8041(3) 0.6076(3) 0.50797(16) 0.0851(8) Uani 1 1 d . . . H6 H 0.8758 0.6586 0.5397 0.102 Uiso 1 1 calc R . . C7 C 0.6864(3) 0.6797(3) 0.48525(17) 0.0855(9) Uani 1 1 d . . . H7 H 0.6777 0.7797 0.5010 0.103 Uiso 1 1 calc R . . C8 C 0.5803(3) 0.6041(3) 0.43889(16) 0.0737(7) Uani 1 1 d . . . H8 H 0.4993 0.6528 0.4235 0.088 Uiso 1 1 calc R . . C9 C 0.5934(2) 0.4563(2) 0.41509(12) 0.0555(5) Uani 1 1 d . . . H9 H 0.5207 0.4057 0.3841 0.067 Uiso 1 1 calc R . . C10 C 0.45255(16) -0.0300(2) 0.30722(11) 0.0425(4) Uani 1 1 d . . . C11 C 0.40314(19) -0.0173(2) 0.37422(13) 0.0548(5) Uani 1 1 d . . . H11 H 0.4427 0.0496 0.4147 0.066 Uiso 1 1 calc R . . C12 C 0.2965(2) -0.1021(3) 0.38195(17) 0.0745(7) Uani 1 1 d . . . H12 H 0.2650 -0.0930 0.4275 0.089 Uiso 1 1 calc R . . C13 C 0.2370(2) -0.1999(3) 0.3223(2) 0.0971(10) Uani 1 1 d . . . H13 H 0.1645 -0.2567 0.3271 0.117 Uiso 1 1 calc R . . C14 C 0.2834(3) -0.2140(4) 0.2565(2) 0.1061(11) Uani 1 1 d . . . H14 H 0.2425 -0.2807 0.2162 0.127 Uiso 1 1 calc R . . C15 C 0.3920(2) -0.1300(3) 0.24825(15) 0.0753(7) Uani 1 1 d . . . H15 H 0.4235 -0.1415 0.2029 0.090 Uiso 1 1 calc R . . C16 C 0.78107(17) 0.1275(2) 0.23892(11) 0.0451(5) Uani 1 1 d . . . H16A H 0.8098 0.1532 0.1914 0.054 Uiso 1 1 calc R . . H16B H 0.7810 0.2210 0.2688 0.054 Uiso 1 1 calc R . . C17 C 0.88200(17) 0.0200(2) 0.28919(12) 0.0484(5) Uani 1 1 d . . . H17A H 0.8819 -0.0729 0.2588 0.058 Uiso 1 1 calc R . . H17B H 0.9680 0.0663 0.2959 0.058 Uiso 1 1 calc R . . C18 C 0.86679(19) -0.0245(2) 0.37129(11) 0.0486(5) Uani 1 1 d . . . H18A H 0.9335 -0.0998 0.3935 0.058 Uiso 1 1 calc R . . H18B H 0.7818 -0.0730 0.3651 0.058 Uiso 1 1 calc R . . S1 S 0.61401(5) 0.05857(6) 0.20842(3) 0.04584(15) Uani 1 1 d . . . S2 S 0.87932(5) 0.12954(6) 0.44246(3) 0.05662(18) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0359(8) 0.0349(9) 0.0399(9) -0.0031(8) 0.0088(7) 0.0049(8) C2 0.0397(9) 0.0429(10) 0.0428(10) -0.0026(8) 0.0153(8) 0.0005(9) C3 0.0446(10) 0.0446(10) 0.0356(9) -0.0038(8) 0.0124(8) -0.0064(9) C4 0.0569(11) 0.0442(10) 0.0386(10) -0.0063(8) 0.0227(9) -0.0088(10) C5 0.0698(14) 0.0679(15) 0.0634(14) -0.0260(12) 0.0197(12) -0.0191(12) C6 0.099(2) 0.0764(17) 0.090(2) -0.0458(15) 0.0408(16) -0.0318(17) C7 0.132(2) 0.0512(13) 0.099(2) -0.0287(14) 0.0762(19) -0.0195(17) C8 0.0959(19) 0.0558(14) 0.0860(18) -0.0031(13) 0.0542(16) 0.0105(14) C9 0.0642(13) 0.0546(13) 0.0552(12) -0.0043(10) 0.0293(10) -0.0037(11) C10 0.0352(9) 0.0388(10) 0.0527(11) -0.0040(8) 0.0092(8) 0.0004(8) C11 0.0536(12) 0.0518(12) 0.0632(13) -0.0021(10) 0.0224(10) -0.0028(10) C12 0.0656(14) 0.0713(16) 0.098(2) 0.0061(15) 0.0428(14) -0.0078(14) C13 0.0660(16) 0.090(2) 0.145(3) -0.013(2) 0.0434(19) -0.0370(16) C14 0.085(2) 0.114(2) 0.122(3) -0.049(2) 0.0307(19) -0.0613(19) C15 0.0656(14) 0.0856(18) 0.0780(17) -0.0314(14) 0.0241(13) -0.0278(14) C16 0.0514(11) 0.0420(10) 0.0480(11) 0.0027(9) 0.0238(9) 0.0003(9) C17 0.0423(10) 0.0442(11) 0.0617(13) -0.0035(9) 0.0183(9) 0.0022(9) C18 0.0487(10) 0.0415(10) 0.0522(12) 0.0009(9) 0.0063(9) 0.0073(9) S1 0.0512(3) 0.0493(3) 0.0371(3) -0.0032(2) 0.0111(2) 0.0026(2) S2 0.0516(3) 0.0605(3) 0.0496(3) -0.0088(2) -0.0029(2) 0.0032(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.311(2) . ? C1 C10 1.475(2) . ? C1 S1 1.7859(18) . ? C2 C3 1.310(2) . ? C3 C4 1.483(2) . ? C3 S2 1.7881(19) . ? C4 C5 1.379(3) . ? C4 C9 1.388(3) . ? C5 C6 1.392(3) . ? C5 H5 0.9300 . ? C6 C7 1.356(4) . ? C6 H6 0.9300 . ? C7 C8 1.372(4) . ? C7 H7 0.9300 . ? C8 C9 1.378(3) . ? C8 H8 0.9300 . ? C9 H9 0.9300 . ? C10 C15 1.377(3) . ? C10 C11 1.386(3) . ? C11 C12 1.378(3) . ? C11 H11 0.9300 . ? C12 C13 1.369(4) . ? C12 H12 0.9300 . ? C13 C14 1.350(4) . ? C13 H13 0.9300 . ? C14 C15 1.393(3) . ? C14 H14 0.9300 . ? C15 H15 0.9300 . ? C16 C17 1.522(2) . ? C16 S1 1.8058(18) . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C17 C18 1.520(3) . ? C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? C18 S2 1.8119(19) . ? C18 H18A 0.9700 . ? C18 H18B 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 C2 C1 C10 123.19(17) . . ? C2 C1 S1 118.97(14) . . ? C10 C1 S1 117.84(13) . . ? C3 C2 C1 162.40(18) . . ? C2 C3 C4 123.98(17) . . ? C2 C3 S2 118.49(14) . . ? C4 C3 S2 117.53(14) . . ? C5 C4 C9 118.29(19) . . ? C5 C4 C3 122.39(19) . . ? C9 C4 C3 119.32(18) . . ? C4 C5 C6 120.1(2) . . ? C4 C5 H5 119.9 . . ? C6 C5 H5 119.9 . . ? C7 C6 C5 120.9(2) . . ? C7 C6 H6 119.5 . . ? C5 C6 H6 119.5 . . ? C6 C7 C8 119.5(2) . . ? C6 C7 H7 120.2 . . ? C8 C7 H7 120.2 . . ? C7 C8 C9 120.3(2) . . ? C7 C8 H8 119.9 . . ? C9 C8 H8 119.9 . . ? C8 C9 C4 120.8(2) . . ? C8 C9 H9 119.6 . . ? C4 C9 H9 119.6 . . ? C15 C10 C11 118.15(18) . . ? C15 C10 C1 122.10(18) . . ? C11 C10 C1 119.74(17) . . ? C12 C11 C10 121.2(2) . . ? C12 C11 H11 119.4 . . ? C10 C11 H11 119.4 . . ? C13 C12 C11 119.7(2) . . ? C13 C12 H12 120.1 . . ? C11 C12 H12 120.1 . . ? C14 C13 C12 120.1(2) . . ? C14 C13 H13 120.0 . . ? C12 C13 H13 120.0 . . ? C13 C14 C15 120.8(3) . . ? C13 C14 H14 119.6 . . ? C15 C14 H14 119.6 . . ? C10 C15 C14 120.1(2) . . ? C10 C15 H15 120.0 . . ? C14 C15 H15 120.0 . . ? C17 C16 S1 116.62(13) . . ? C17 C16 H16A 108.1 . . ? S1 C16 H16A 108.1 . . ? C17 C16 H16B 108.1 . . ? S1 C16 H16B 108.1 . . ? H16A C16 H16B 107.3 . . ? C18 C17 C16 118.41(15) . . ? C18 C17 H17A 107.7 . . ? C16 C17 H17A 107.7 . . ? C18 C17 H17B 107.7 . . ? C16 C17 H17B 107.7 . . ? H17A C17 H17B 107.1 . . ? C17 C18 S2 115.93(13) . . ? C17 C18 H18A 108.3 . . ? S2 C18 H18A 108.3 . . ? C17 C18 H18B 108.3 . . ? S2 C18 H18B 108.3 . . ? H18A C18 H18B 107.4 . . ? C1 S1 C16 101.49(9) . . ? C3 S2 C18 102.18(9) . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.277 _refine_diff_density_min -0.414 _refine_diff_density_rms 0.096 # Attachment '4.cif' data_8405 _database_code_depnum_ccdc_archive 'CCDC 720412' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H16 O4 S2' _chemical_formula_weight 360.43 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 11.306(2) _cell_length_b 10.818(2) _cell_length_c 14.594(3) _cell_angle_alpha 90.00 _cell_angle_beta 111.03(3) _cell_angle_gamma 90.00 _cell_volume 1666.1(6) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 15234 _cell_measurement_theta_min 2.40 _cell_measurement_theta_max 27.48 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.437 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 752 _exptl_absorpt_coefficient_mu 0.339 _exptl_absorpt_correction_type Empirical _exptl_absorpt_correction_T_min 0.8226 _exptl_absorpt_correction_T_max 0.9353 _exptl_absorpt_process_details ; HIGASHI, T. (1995). Abscor-Empirical Absorption Correction based on Fourier Series Approximation. Rigaku Corporation,Tokyo,Japan. ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku RAXIS RAPID IP' _diffrn_measurement_method \W _diffrn_detector_area_resol_mean 10.00 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 15234 _diffrn_reflns_av_R_equivalents 0.04663386 _diffrn_reflns_av_sigmaI/netI 0.0540 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.40 _diffrn_reflns_theta_max 27.48 _reflns_number_total 3821 _reflns_number_gt 2755 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Rapid-AUTO (Rigaku,2000)' _computing_cell_refinement Rapid-AUTO _computing_data_reduction 'CrystalStructure (Rigaku/MSC,2000)' _computing_structure_solution SHELXS-97,(Sheldrick,1997) _computing_structure_refinement SHELXL-97,(Sheldrick,1997) _computing_molecular_graphics 'Siemens SHELXTL V4.2,(Sheldrick,1990)' _computing_publication_material SHELXL-97,(Sheldrick,1997) _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^)+(0.0480P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment none _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0183(14) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3821 _refine_ls_number_parameters 218 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0563 _refine_ls_R_factor_gt 0.0384 _refine_ls_wR_factor_ref 0.0988 _refine_ls_wR_factor_gt 0.0947 _refine_ls_goodness_of_fit_ref 0.990 _refine_ls_restrained_S_all 0.990 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.73629(15) 0.82507(16) 0.25965(11) 0.0319(4) Uani 1 1 d . . . C2 C 0.76395(16) 0.89383(16) 0.19692(12) 0.0341(4) Uani 1 1 d . . . C3 C 0.81210(16) 0.96085(15) 0.14469(12) 0.0321(4) Uani 1 1 d . . . C4 C 1.03324(18) 0.83706(18) 0.27486(13) 0.0418(4) Uani 1 1 d . . . H4A H 0.9797 0.7644 0.2642 0.050 Uiso 1 1 calc R . . H4B H 1.1178 0.8089 0.2828 0.050 Uiso 1 1 calc R . . C5 C 1.03877(18) 0.8977(2) 0.37143(13) 0.0475(5) Uani 1 1 d . . . H5A H 1.1259 0.8958 0.4168 0.057 Uiso 1 1 calc R . . H5B H 1.0148 0.9838 0.3584 0.057 Uiso 1 1 calc R . . C6 C 0.95552(17) 0.83953(19) 0.42173(12) 0.0434(5) Uani 1 1 d . . . H6A H 0.9936 0.8553 0.4917 0.052 Uiso 1 1 calc R . . H6B H 0.9548 0.7507 0.4123 0.052 Uiso 1 1 calc R . . C7 C 0.68524(14) 0.69815(17) 0.23928(12) 0.0326(4) Uani 1 1 d . . . C8 C 0.62848(19) 0.63757(19) 0.29653(15) 0.0493(5) Uani 1 1 d . . . H8 H 0.6232 0.6760 0.3519 0.059 Uiso 1 1 calc R . . C9 C 0.5799(2) 0.5203(2) 0.27120(19) 0.0651(7) Uani 1 1 d . . . H9 H 0.5420 0.4801 0.3098 0.078 Uiso 1 1 calc R . . C10 C 0.5869(2) 0.4626(2) 0.1901(2) 0.0663(7) Uani 1 1 d . . . H10 H 0.5545 0.3831 0.1742 0.080 Uiso 1 1 calc R . . C11 C 0.64202(19) 0.5221(2) 0.13150(16) 0.0541(6) Uani 1 1 d . . . H11 H 0.6453 0.4837 0.0755 0.065 Uiso 1 1 calc R . . C12 C 0.69150(17) 0.63774(18) 0.15663(13) 0.0404(4) Uani 1 1 d . . . H12 H 0.7301 0.6770 0.1180 0.048 Uiso 1 1 calc R . . C13 C 0.74928(16) 1.06152(16) 0.07535(12) 0.0337(4) Uani 1 1 d . . . C14 C 0.6412(2) 1.1152(2) 0.08116(16) 0.0543(6) Uani 1 1 d . . . H14 H 0.6099 1.0884 0.1286 0.065 Uiso 1 1 calc R . . C15 C 0.5794(2) 1.2083(2) 0.01691(16) 0.0611(6) Uani 1 1 d . . . H15 H 0.5055 1.2425 0.0203 0.073 Uiso 1 1 calc R . . C16 C 0.62672(19) 1.25057(18) -0.05184(14) 0.0501(5) Uani 1 1 d . . . H16 H 0.5858 1.3140 -0.0945 0.060 Uiso 1 1 calc R . . C17 C 0.73414(18) 1.19894(19) -0.05719(13) 0.0476(5) Uani 1 1 d . . . H17 H 0.7666 1.2282 -0.1033 0.057 Uiso 1 1 calc R . . C18 C 0.79549(18) 1.10375(18) 0.00502(13) 0.0421(4) Uani 1 1 d . . . H18 H 0.8676 1.0682 -0.0004 0.050 Uiso 1 1 calc R . . O1 O 0.98544(14) 0.85808(14) 0.08795(10) 0.0553(4) Uani 1 1 d . . . O2 O 1.04037(12) 1.04687(12) 0.18791(10) 0.0477(4) Uani 1 1 d . . . O3 O 0.79771(16) 1.02417(14) 0.36863(11) 0.0655(5) Uani 1 1 d . . . O4 O 0.73493(14) 0.84175(16) 0.44122(9) 0.0667(5) Uani 1 1 d . . . S1 S 0.97655(4) 0.93003(4) 0.16723(3) 0.03410(14) Uani 1 1 d . . . S2 S 0.79727(5) 0.89268(5) 0.38011(3) 0.04436(16) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0314(8) 0.0382(10) 0.0297(8) 0.0042(7) 0.0154(7) 0.0042(7) C2 0.0327(9) 0.0337(10) 0.0353(9) 0.0007(7) 0.0115(7) 0.0004(7) C3 0.0362(9) 0.0292(10) 0.0331(9) -0.0019(7) 0.0151(7) -0.0030(7) C4 0.0404(10) 0.0353(10) 0.0540(11) 0.0122(9) 0.0220(8) 0.0102(8) C5 0.0398(11) 0.0576(14) 0.0378(10) 0.0088(9) 0.0052(8) -0.0035(10) C6 0.0476(11) 0.0487(12) 0.0301(9) 0.0044(8) 0.0096(8) 0.0019(9) C7 0.0265(8) 0.0379(10) 0.0349(9) 0.0083(7) 0.0130(7) 0.0027(7) C8 0.0543(12) 0.0477(13) 0.0570(12) 0.0125(10) 0.0335(10) 0.0022(10) C9 0.0594(14) 0.0507(14) 0.0977(19) 0.0218(13) 0.0434(13) -0.0055(12) C10 0.0528(13) 0.0393(13) 0.106(2) 0.0002(13) 0.0277(13) -0.0084(11) C11 0.0474(12) 0.0466(13) 0.0665(14) -0.0129(11) 0.0182(10) -0.0038(10) C12 0.0371(10) 0.0433(12) 0.0420(10) 0.0019(8) 0.0157(8) -0.0022(8) C13 0.0363(9) 0.0299(9) 0.0340(9) 0.0004(7) 0.0115(7) -0.0028(7) C14 0.0554(13) 0.0552(14) 0.0625(13) 0.0163(11) 0.0337(11) 0.0120(11) C15 0.0549(13) 0.0579(15) 0.0753(15) 0.0172(12) 0.0294(11) 0.0206(12) C16 0.0517(12) 0.0408(11) 0.0491(11) 0.0102(9) 0.0077(9) 0.0032(10) C17 0.0481(11) 0.0519(13) 0.0410(10) 0.0138(9) 0.0137(9) -0.0039(10) C18 0.0404(10) 0.0454(12) 0.0433(10) 0.0095(9) 0.0186(8) 0.0007(9) O1 0.0693(10) 0.0566(10) 0.0550(8) -0.0097(7) 0.0407(7) 0.0029(7) O2 0.0413(7) 0.0357(8) 0.0606(9) 0.0068(6) 0.0116(6) -0.0113(6) O3 0.0846(12) 0.0419(9) 0.0650(10) -0.0131(7) 0.0207(9) 0.0167(8) O4 0.0692(10) 0.1037(13) 0.0414(8) -0.0026(8) 0.0370(7) 0.0028(9) S1 0.0366(2) 0.0305(3) 0.0400(3) 0.00171(18) 0.01946(19) -0.00109(19) S2 0.0527(3) 0.0488(3) 0.0357(3) -0.0055(2) 0.0208(2) 0.0070(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.302(2) . ? C1 C7 1.478(2) . ? C1 S2 1.7975(17) . ? C2 C3 1.304(2) . ? C3 C13 1.483(2) . ? C3 S1 1.7992(18) . ? C4 C5 1.535(3) . ? C4 S1 1.7797(18) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 C6 1.522(2) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 S2 1.7666(19) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 C8 1.387(2) . ? C7 C12 1.396(2) . ? C8 C9 1.379(3) . ? C8 H8 0.9300 . ? C9 C10 1.365(4) . ? C9 H9 0.9300 . ? C10 C11 1.385(3) . ? C10 H10 0.9300 . ? C11 C12 1.366(3) . ? C11 H11 0.9300 . ? C12 H12 0.9300 . ? C13 C14 1.382(3) . ? C13 C18 1.386(2) . ? C14 C15 1.384(3) . ? C14 H14 0.9300 . ? C15 C16 1.374(3) . ? C15 H15 0.9300 . ? C16 C17 1.364(3) . ? C16 H16 0.9300 . ? C17 C18 1.383(3) . ? C17 H17 0.9300 . ? C18 H18 0.9300 . ? O1 S1 1.4276(13) . ? O2 S1 1.4329(13) . ? O3 S2 1.4325(16) . ? O4 S2 1.4307(14) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C7 124.37(15) . . ? C2 C1 S2 110.53(14) . . ? C7 C1 S2 124.05(12) . . ? C1 C2 C3 169.96(18) . . ? C2 C3 C13 127.52(16) . . ? C2 C3 S1 114.26(13) . . ? C13 C3 S1 118.12(12) . . ? C5 C4 S1 116.86(14) . . ? C5 C4 H4A 108.1 . . ? S1 C4 H4A 108.1 . . ? C5 C4 H4B 108.1 . . ? S1 C4 H4B 108.1 . . ? H4A C4 H4B 107.3 . . ? C6 C5 C4 115.93(17) . . ? C6 C5 H5A 108.3 . . ? C4 C5 H5A 108.3 . . ? C6 C5 H5B 108.3 . . ? C4 C5 H5B 108.3 . . ? H5A C5 H5B 107.4 . . ? C5 C6 S2 115.14(13) . . ? C5 C6 H6A 108.5 . . ? S2 C6 H6A 108.5 . . ? C5 C6 H6B 108.5 . . ? S2 C6 H6B 108.5 . . ? H6A C6 H6B 107.5 . . ? C8 C7 C12 118.50(18) . . ? C8 C7 C1 123.34(16) . . ? C12 C7 C1 118.14(15) . . ? C9 C8 C7 119.9(2) . . ? C9 C8 H8 120.0 . . ? C7 C8 H8 120.0 . . ? C10 C9 C8 120.8(2) . . ? C10 C9 H9 119.6 . . ? C8 C9 H9 119.6 . . ? C9 C10 C11 120.1(2) . . ? C9 C10 H10 120.0 . . ? C11 C10 H10 120.0 . . ? C12 C11 C10 119.5(2) . . ? C12 C11 H11 120.3 . . ? C10 C11 H11 120.3 . . ? C11 C12 C7 121.21(18) . . ? C11 C12 H12 119.4 . . ? C7 C12 H12 119.4 . . ? C14 C13 C18 118.92(17) . . ? C14 C13 C3 118.94(16) . . ? C18 C13 C3 122.15(16) . . ? C13 C14 C15 120.48(19) . . ? C13 C14 H14 119.8 . . ? C15 C14 H14 119.8 . . ? C16 C15 C14 120.2(2) . . ? C16 C15 H15 119.9 . . ? C14 C15 H15 119.9 . . ? C17 C16 C15 119.60(19) . . ? C17 C16 H16 120.2 . . ? C15 C16 H16 120.2 . . ? C16 C17 C18 120.94(18) . . ? C16 C17 H17 119.5 . . ? C18 C17 H17 119.5 . . ? C17 C18 C13 119.87(18) . . ? C17 C18 H18 120.1 . . ? C13 C18 H18 120.1 . . ? O1 S1 O2 118.37(9) . . ? O1 S1 C4 107.42(9) . . ? O2 S1 C4 108.54(9) . . ? O1 S1 C3 108.75(8) . . ? O2 S1 C3 106.52(8) . . ? C4 S1 C3 106.70(9) . . ? O4 S2 O3 118.59(10) . . ? O4 S2 C6 108.97(9) . . ? O3 S2 C6 108.53(10) . . ? O4 S2 C1 110.56(9) . . ? O3 S2 C1 107.81(9) . . ? C6 S2 C1 100.92(9) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.290 _refine_diff_density_min -0.284 _refine_diff_density_rms 0.050