# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_bd115 _database_code_depnum_ccdc_archive 'CCDC 927826' #TrackingRef 'bd115n.final.cif' # structure by Linda JW Shimon # Orii Gidron Michael Bendikov _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C16 H10 O2 S2' _chemical_formula_sum 'C16 H10 O2 S2' _chemical_formula_weight 298.36 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 _symmetry_space_group_name_Hall '-P 2ybc' 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 15.8370(17) _cell_length_b 5.4707(6) _cell_length_c 7.9739(8) _cell_angle_alpha 90.00 _cell_angle_beta 102.726(3) _cell_angle_gamma 90.00 _cell_volume 673.88(12) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 11783 _cell_measurement_theta_min 1.30 _cell_measurement_theta_max 30.75 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.470 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 308 _exptl_absorpt_coefficient_mu 0.392 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8916 _exptl_absorpt_correction_T_max 0.9694 _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 KappaApexII CCD' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 11783 _diffrn_reflns_av_R_equivalents 0.0341 _diffrn_reflns_av_sigmaI/netI 0.0243 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 1.32 _diffrn_reflns_theta_max 30.75 _reflns_number_total 2077 _reflns_number_gt 1719 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker Apex2' _computing_cell_refinement 'Bruker Apex2' _computing_data_reduction 'Bruker Apex2' _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^)+(0.0478P)^2^+0.1526P] 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 2077 _refine_ls_number_parameters 98 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0438 _refine_ls_R_factor_gt 0.0339 _refine_ls_wR_factor_ref 0.0954 _refine_ls_wR_factor_gt 0.0893 _refine_ls_goodness_of_fit_ref 1.073 _refine_ls_restrained_S_all 1.073 _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 S1A S 0.21402(8) 1.2308(2) 1.00015(16) 0.0236(2) Uani 0.4510(15) 1 d P A 1 C6A C 0.1561(4) 0.8509(11) 0.8216(8) 0.0236(2) Uani 0.4510(15) 1 d P A 1 H6A H 0.1528 0.7026 0.7585 0.028 Uiso 0.4510(15) 1 calc PR A 1 S1B S 0.14454(6) 0.81618(18) 0.80051(13) 0.0265(2) Uani 0.5490(15) 1 d P A 2 C6B C 0.2067(3) 1.1899(9) 0.9791(7) 0.0265(2) Uani 0.5490(15) 1 d P A 2 H6B H 0.2451 1.3090 1.0404 0.032 Uiso 0.5490(15) 1 calc PR A 2 O1 O 0.38534(5) 1.05153(15) 0.97522(10) 0.02160(18) Uani 1 1 d . . . C1 C 0.46079(6) 0.9379(2) 0.96054(13) 0.0215(2) Uani 1 1 d . . . C2 C 0.44330(7) 0.7238(2) 0.87236(14) 0.0245(2) Uani 1 1 d . . . H2 H 0.4842 0.6129 0.8442 0.029 Uiso 1 1 calc R . . C3 C 0.35166(7) 0.6993(2) 0.83080(14) 0.0251(2) Uani 1 1 d . . . H3 H 0.3194 0.5680 0.7700 0.030 Uiso 1 1 calc R . . C4 C 0.31900(7) 0.9002(2) 0.89498(13) 0.0216(2) Uani 1 1 d . A . C5 C 0.23257(7) 0.9789(2) 0.89781(13) 0.0219(2) Uani 1 1 d . . . C7 C 0.07802(8) 0.9989(3) 0.86039(16) 0.0347(3) Uani 1 1 d . . . H7 H 0.0185 0.9576 0.8247 0.042 Uiso 1 1 calc R A 1 C8 C 0.11097(8) 1.1960(2) 0.95387(16) 0.0315(3) Uani 1 1 d . A . H8 H 0.0741 1.3111 0.9913 0.038 Uiso 1 1 calc R B 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 S1A 0.0204(4) 0.0235(5) 0.0268(5) -0.0031(3) 0.0053(3) 0.0005(3) C6A 0.0204(4) 0.0235(5) 0.0268(5) -0.0031(3) 0.0053(3) 0.0005(3) S1B 0.0217(4) 0.0260(5) 0.0301(4) -0.0007(3) 0.0021(3) -0.0033(2) C6B 0.0217(4) 0.0260(5) 0.0301(4) -0.0007(3) 0.0021(3) -0.0033(2) O1 0.0175(4) 0.0238(4) 0.0239(4) -0.0003(3) 0.0053(3) 0.0013(3) C1 0.0191(5) 0.0261(6) 0.0204(5) 0.0025(4) 0.0069(4) 0.0033(4) C2 0.0242(5) 0.0274(6) 0.0230(5) -0.0013(4) 0.0073(4) 0.0028(4) C3 0.0252(5) 0.0275(6) 0.0226(5) -0.0032(4) 0.0057(4) -0.0012(4) C4 0.0207(5) 0.0249(5) 0.0190(5) 0.0013(4) 0.0043(4) -0.0009(4) C5 0.0199(5) 0.0262(5) 0.0198(5) 0.0031(4) 0.0046(4) 0.0006(4) C7 0.0231(5) 0.0469(8) 0.0321(6) 0.0090(6) 0.0017(5) -0.0076(5) C8 0.0325(6) 0.0342(7) 0.0300(6) 0.0042(5) 0.0115(5) 0.0103(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 S1A C8 1.6032(18) . ? S1A C5 1.6603(15) . ? C6A C5 1.415(5) . ? C6A C7 1.565(6) . ? C6A H6A 0.9500 . ? S1B C7 1.5996(19) . ? S1B C5 1.6918(13) . ? C6B C5 1.427(5) . ? C6B C8 1.486(5) . ? C6B H6B 0.9500 . ? O1 C1 1.3747(12) . ? O1 C4 1.3794(13) . ? C1 C2 1.3628(16) . ? C1 C1 1.434(2) 3_677 ? C2 C3 1.4220(16) . ? C2 H2 0.9500 . ? C3 C4 1.3616(16) . ? C3 H3 0.9500 . ? C4 C5 1.4399(15) . ? C7 C8 1.349(2) . ? C7 H7 0.9500 . ? C8 H8 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C8 S1A C5 94.00(7) . . ? C5 C6A C7 107.3(4) . . ? C5 C6A H6A 126.3 . . ? C7 C6A H6A 126.3 . . ? C7 S1B C5 93.70(7) . . ? C5 C6B C8 110.1(3) . . ? C5 C6B H6B 125.0 . . ? C8 C6B H6B 125.0 . . ? C1 O1 C4 106.06(9) . . ? C2 C1 O1 110.54(9) . . ? C2 C1 C1 133.78(13) . 3_677 ? O1 C1 C1 115.68(12) . 3_677 ? C1 C2 C3 106.40(10) . . ? C1 C2 H2 126.8 . . ? C3 C2 H2 126.8 . . ? C4 C3 C2 106.80(10) . . ? C4 C3 H3 126.6 . . ? C2 C3 H3 126.6 . . ? C3 C4 O1 110.20(9) . . ? C3 C4 C5 133.52(11) . . ? O1 C4 C5 116.27(10) . . ? C6A C5 C6B 106.9(3) . . ? C6A C5 C4 124.9(3) . . ? C6B C5 C4 128.2(2) . . ? C6A C5 S1A 113.2(3) . . ? C4 C5 S1A 121.86(9) . . ? C6A C5 S1B 3.3(3) . . ? C6B C5 S1B 110.1(2) . . ? C4 C5 S1B 121.71(10) . . ? S1A C5 S1B 116.42(8) . . ? C8 C7 C6A 107.3(2) . . ? C8 C7 S1B 117.68(10) . . ? C6A C7 S1B 10.46(19) . . ? C8 C7 H7 126.4 . . ? C6A C7 H7 126.4 . . ? S1B C7 H7 115.9 . . ? C7 C8 C6B 108.4(2) . . ? C7 C8 S1A 118.19(11) . . ? C6B C8 S1A 9.8(2) . . ? C7 C8 H8 120.9 . . ? C6B C8 H8 130.7 . . ? S1A C8 H8 120.9 . . ? 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 C4 O1 C1 C2 0.77(12) . . . . ? C4 O1 C1 C1 -178.65(11) . . . 3_677 ? O1 C1 C2 C3 -0.74(12) . . . . ? C1 C1 C2 C3 178.54(15) 3_677 . . . ? C1 C2 C3 C4 0.41(12) . . . . ? C2 C3 C4 O1 0.06(12) . . . . ? C2 C3 C4 C5 -178.61(11) . . . . ? C1 O1 C4 C3 -0.50(12) . . . . ? C1 O1 C4 C5 178.42(9) . . . . ? C7 C6A C5 C6B 0.2(4) . . . . ? C7 C6A C5 C4 178.51(18) . . . . ? C7 C6A C5 S1A 0.6(5) . . . . ? C7 C6A C5 S1B -167(6) . . . . ? C8 C6B C5 C6A 0.0(4) . . . . ? C8 C6B C5 C4 -178.21(17) . . . . ? C8 C6B C5 S1A -176(3) . . . . ? C8 C6B C5 S1B 0.8(4) . . . . ? C3 C4 C5 C6A -2.0(4) . . . . ? O1 C4 C5 C6A 179.4(3) . . . . ? C3 C4 C5 C6B 175.9(3) . . . . ? O1 C4 C5 C6B -2.7(3) . . . . ? C3 C4 C5 S1A 175.70(12) . . . . ? O1 C4 C5 S1A -2.90(15) . . . . ? C3 C4 C5 S1B -2.95(18) . . . . ? O1 C4 C5 S1B 178.44(9) . . . . ? C8 S1A C5 C6A -0.6(3) . . . . ? C8 S1A C5 C6B 3(2) . . . . ? C8 S1A C5 C4 -178.54(10) . . . . ? C8 S1A C5 S1B 0.19(10) . . . . ? C7 S1B C5 C6A 12(5) . . . . ? C7 S1B C5 C6B -0.9(3) . . . . ? C7 S1B C5 C4 178.20(10) . . . . ? C7 S1B C5 S1A -0.52(10) . . . . ? C5 C6A C7 C8 -0.4(4) . . . . ? C5 C6A C7 S1B 175.8(19) . . . . ? C5 S1B C7 C8 0.76(13) . . . . ? C5 S1B C7 C6A -3.3(15) . . . . ? C6A C7 C8 C6B 0.4(4) . . . . ? S1B C7 C8 C6B -0.4(3) . . . . ? C6A C7 C8 S1A 0.0(3) . . . . ? S1B C7 C8 S1A -0.80(17) . . . . ? C5 C6B C8 C7 -0.3(4) . . . . ? C5 C6B C8 S1A 177.6(19) . . . . ? C5 S1A C8 C7 0.34(14) . . . . ? C5 S1A C8 C6B -2.0(15) . . . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 30.75 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.367 _refine_diff_density_min -0.248 _refine_diff_density_rms 0.048 data_bd126 _database_code_depnum_ccdc_archive 'CCDC 927827' #TrackingRef 'bd126.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C16 H10 O2 S2' _chemical_formula_sum 'C16 H10 O2 S2' _chemical_formula_weight 298.36 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 Orthorhombic _symmetry_space_group_name_H-M Pbca _symmetry_space_group_name_Hall -P2ac2ab loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x+1/2, -y, z+1/2' '-x, -y, -z' '-x-1/2, y-1/2, z' 'x, -y-1/2, z-1/2' 'x-1/2, y, -z-1/2' _cell_length_a 7.4341(7) _cell_length_b 7.5723(6) _cell_length_c 23.450(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1320.1(2) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 11141 _cell_measurement_theta_min 2.04 _cell_measurement_theta_max 27.47 _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.09 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.501 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 616 _exptl_absorpt_coefficient_mu 0.400 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9067 _exptl_absorpt_correction_T_max 0.9920 _exptl_absorpt_process_details 'Bruker SHELXTL' _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 Apex2 CCD' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11141 _diffrn_reflns_av_R_equivalents 0.0470 _diffrn_reflns_av_sigmaI/netI 0.0350 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 30 _diffrn_reflns_theta_min 3.24 _diffrn_reflns_theta_max 27.47 _reflns_number_total 1503 _reflns_number_gt 1240 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker Apex2' _computing_cell_refinement 'Bruker Apex2' _computing_data_reduction 'Bruker Apex2' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0386P)^2^+1.2489P] 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 1503 _refine_ls_number_parameters 91 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0540 _refine_ls_R_factor_gt 0.0397 _refine_ls_wR_factor_ref 0.1019 _refine_ls_wR_factor_gt 0.0943 _refine_ls_goodness_of_fit_ref 1.092 _refine_ls_restrained_S_all 1.092 _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 -0.05386(6) 0.26398(6) 0.96553(2) 0.01997(17) Uani 1 1 d . . . O1 O 0.06089(19) 0.42061(17) 0.80707(6) 0.0236(3) Uani 1 1 d . . . C1 C 0.0165(3) 0.5803(3) 0.78268(10) 0.0258(5) Uani 1 1 d . . . H1 H 0.0492 0.6153 0.7452 0.031 Uiso 1 1 calc R . . C2 C -0.0789(3) 0.6792(3) 0.81900(10) 0.0268(5) Uani 1 1 d . . . H2 H -0.1254 0.7941 0.8121 0.032 Uiso 1 1 calc R . . C3 C -0.0971(3) 0.5786(3) 0.87001(10) 0.0234(5) Uani 1 1 d . . . H3 H -0.1580 0.6136 0.9038 0.028 Uiso 1 1 calc R . . C4 C -0.0110(2) 0.4236(2) 0.86106(9) 0.0187(4) Uani 1 1 d . . . C5 C 0.0159(2) 0.2678(2) 0.89531(9) 0.0193(4) Uani 1 1 d . . . C6 C 0.0883(3) 0.1090(2) 0.87933(9) 0.0212(4) Uani 1 1 d . . . H6 H 0.1350 0.0861 0.8424 0.025 Uiso 1 1 calc R . . C7 C 0.0860(2) -0.0168(2) 0.92365(9) 0.0205(4) Uani 1 1 d . . . H7 H 0.1311 -0.1335 0.9195 0.025 Uiso 1 1 calc R . . C8 C 0.0124(2) 0.0453(2) 0.97332(8) 0.0184(4) 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 S1 0.0215(3) 0.0163(2) 0.0221(3) -0.00254(18) 0.0012(2) 0.00143(17) O1 0.0283(7) 0.0229(7) 0.0197(8) -0.0013(6) 0.0015(6) 0.0006(6) C1 0.0307(11) 0.0246(9) 0.0221(12) 0.0053(8) -0.0041(9) -0.0014(9) C2 0.0254(10) 0.0216(9) 0.0333(14) 0.0023(9) -0.0039(10) 0.0000(8) C3 0.0211(9) 0.0227(9) 0.0265(13) -0.0009(8) 0.0024(9) 0.0011(8) C4 0.0150(8) 0.0212(9) 0.0200(11) -0.0023(7) -0.0008(8) -0.0030(7) C5 0.0142(8) 0.0202(9) 0.0237(12) -0.0013(8) -0.0014(8) -0.0026(7) C6 0.0172(9) 0.0228(9) 0.0236(12) -0.0035(8) 0.0005(8) 0.0002(7) C7 0.0173(9) 0.0200(9) 0.0242(12) -0.0034(8) 0.0000(8) 0.0021(7) C8 0.0146(8) 0.0178(8) 0.0227(11) -0.0023(7) -0.0016(8) 0.0006(7) _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 1.727(2) . ? S1 C8 1.7373(19) . ? O1 C4 1.374(3) . ? O1 C1 1.378(2) . ? C1 C2 1.338(3) . ? C1 H1 0.9500 . ? C2 C3 1.425(3) . ? C2 H2 0.9500 . ? C3 C4 1.353(3) . ? C3 H3 0.9500 . ? C4 C5 1.441(3) . ? C5 C6 1.369(3) . ? C6 C7 1.410(3) . ? C6 H6 0.9500 . ? C7 C8 1.370(3) . ? C7 H7 0.9500 . ? C8 C8 1.439(4) 5_557 ? 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 C8 91.78(9) . . ? C4 O1 C1 105.96(16) . . ? C2 C1 O1 110.7(2) . . ? C2 C1 H1 124.6 . . ? O1 C1 H1 124.6 . . ? C1 C2 C3 106.60(18) . . ? C1 C2 H2 126.7 . . ? C3 C2 H2 126.7 . . ? C4 C3 C2 106.77(19) . . ? C4 C3 H3 126.6 . . ? C2 C3 H3 126.6 . . ? C3 C4 O1 109.94(18) . . ? C3 C4 C5 133.6(2) . . ? O1 C4 C5 116.48(17) . . ? C6 C5 C4 128.4(2) . . ? C6 C5 S1 111.36(15) . . ? C4 C5 S1 120.23(15) . . ? C5 C6 C7 112.76(19) . . ? C5 C6 H6 123.6 . . ? C7 C6 H6 123.6 . . ? C8 C7 C6 113.53(17) . . ? C8 C7 H7 123.2 . . ? C6 C7 H7 123.2 . . ? C7 C8 C8 128.8(2) . 5_557 ? C7 C8 S1 110.55(14) . . ? C8 C8 S1 120.64(19) 5_557 . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C4 O1 C1 C2 -0.2(2) . . . . ? O1 C1 C2 C3 0.2(2) . . . . ? C1 C2 C3 C4 -0.1(2) . . . . ? C2 C3 C4 O1 0.0(2) . . . . ? C2 C3 C4 C5 -178.9(2) . . . . ? C1 O1 C4 C3 0.1(2) . . . . ? C1 O1 C4 C5 179.23(17) . . . . ? C3 C4 C5 C6 171.5(2) . . . . ? O1 C4 C5 C6 -7.3(3) . . . . ? C3 C4 C5 S1 -6.1(3) . . . . ? O1 C4 C5 S1 175.08(13) . . . . ? C8 S1 C5 C6 -0.72(15) . . . . ? C8 S1 C5 C4 177.25(16) . . . . ? C4 C5 C6 C7 -177.19(19) . . . . ? S1 C5 C6 C7 0.6(2) . . . . ? C5 C6 C7 C8 -0.1(2) . . . . ? C6 C7 C8 C8 179.8(2) . . . 5_557 ? C6 C7 C8 S1 -0.5(2) . . . . ? C5 S1 C8 C7 0.69(15) . . . . ? C5 S1 C8 C8 -179.6(2) . . . 5_557 ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.424 _refine_diff_density_min -0.589 _refine_diff_density_rms 0.075