# Supplementary Material (ESI) for Dalton Transactions # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 loop_ _publ_author_name _publ_author_address A.Mailman ;Department of Chemistry University of New Brunswick Fredericton, NB E3B 6E2 Canada ; J.Passmore ;Department of Chemistry University of New Brunswick Fredericton, NB E3B 6E2 Canada ; M.Rautiainen '' A.Decken '' W.Scherer '' ; E.-W.Scheidt ; '' _publ_contact_author_name 'Andreas Decken' _publ_contact_author_email adecken@unb.ca _publ_section_title ; The utilization of the cycloaddition and oxidation dehydrogenation chemistry of SNSMF6 (M = As, Sb) salts in the preparation of the 1,4-naphthoquinone fused 1,3,2-dithiazolylium salts and the full characterization of the corresponding prototype hybrid 7p 1,3,2-dithiazolyl radical ; _publ_contact_author_address ;Department of Chemistry University of New Brunswick Fredericton, NB E3B 6E2 Canada ; _publ_contact_author_fax '(506) 453-4981' _publ_contact_author_phone '(506) 453-4875' data_JP030443 _database_code_depnum_ccdc_archive 'CCDC 741234' _publ_section_references ; Bruker (1997-2003). SAINT. Version 6.45. Bruker AXS Inc., Madison, Wisconsin, USA. Bruker (1997-1999). SMART. Version 5.054. Bruker AXS Inc., Madison, Wisconsin, USA. Sheldrick, G.M. (2000). SHELXTL. Version 6.14. Bruker AXS Inc., Madison, Wisconsin, USA. Sheldrick, G.M. (1997). SHELXL97 & SHELXS97. University of Gottingen, Germany. ; _publ_section_exptl_refinement ; ? ; _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '2(C10 H4 N O2 S2), 2(As F6), O2 S' _chemical_formula_sum 'C20 H8 As2 F12 N2 O6 S5' _chemical_formula_weight 910.42 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' N N 0.0061 0.0033 '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' F F 0.0171 0.0103 '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' As As 0.0499 2.0058 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_int_tables_number 14 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 13.9040(17) _cell_length_b 15.1495(18) _cell_length_c 14.0456(18) _cell_angle_alpha 90.00 _cell_angle_beta 99.503(2) _cell_angle_gamma 90.00 _cell_volume 2917.9(6) _cell_formula_units_Z 4 _cell_measurement_temperature 198(1) _cell_measurement_reflns_used 5951 _cell_measurement_theta_min 2.626 _cell_measurement_theta_max 25.640 _exptl_crystal_description Irregular _exptl_crystal_colour Red _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.072 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1776 _exptl_absorpt_coefficient_mu 2.767 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5392 _exptl_absorpt_correction_T_max 0.7616 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1997a)' _exptl_special_details ; Crystal decay was monitored by repeating the initial 50 frames at the end of the data collection and analyzing duplicate reflections. ; _diffrn_ambient_temperature 198(1) _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_source_type 'Bruker AXS SMART1000/P4' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 14046 _diffrn_reflns_av_R_equivalents 0.0311 _diffrn_reflns_av_sigmaI/netI 0.0376 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.48 _diffrn_reflns_theta_max 24.99 _reflns_number_total 4925 _reflns_number_gt 4047 _reflns_threshold_expression >2\s(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _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^)+(0.0374P)^2^+2.6027P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4925 _refine_ls_number_parameters 456 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0425 _refine_ls_R_factor_gt 0.0313 _refine_ls_wR_factor_ref 0.0848 _refine_ls_wR_factor_gt 0.0812 _refine_ls_goodness_of_fit_ref 1.068 _refine_ls_restrained_S_all 1.068 _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 0.30298(6) 0.18846(5) 0.43808(6) 0.0296(2) Uani 1 1 d . . . S2 S 0.43340(6) 0.19367(6) 0.60454(6) 0.0290(2) Uani 1 1 d . . . N1 N 0.4131(2) 0.20317(18) 0.48950(19) 0.0312(6) Uani 1 1 d . . . C1 C 0.1476(2) 0.1459(2) 0.5346(2) 0.0263(7) Uani 1 1 d . . . C2 C 0.2527(2) 0.16689(18) 0.5376(2) 0.0217(7) Uani 1 1 d . . . C3 C 0.3182(2) 0.16979(18) 0.6210(2) 0.0214(7) Uani 1 1 d . . . C4 C 0.2900(2) 0.15559(19) 0.7180(2) 0.0225(7) Uani 1 1 d . . . C5 C 0.1551(3) 0.1164(2) 0.8037(3) 0.0325(8) Uani 1 1 d . . . C6 C 0.0583(3) 0.0952(3) 0.8051(3) 0.0411(9) Uani 1 1 d . . . C7 C -0.0071(3) 0.0904(3) 0.7207(3) 0.0441(10) Uani 1 1 d . . . C8 C 0.0224(3) 0.1070(2) 0.6328(3) 0.0366(8) Uani 1 1 d . . . C9 C 0.1184(2) 0.1285(2) 0.6296(2) 0.0256(7) Uani 1 1 d . . . C10 C 0.1863(2) 0.13313(19) 0.7161(2) 0.0247(7) Uani 1 1 d . . . O1 O 0.09308(17) 0.14366(17) 0.45771(17) 0.0393(6) Uani 1 1 d . . . O2 O 0.35023(16) 0.16321(15) 0.78980(16) 0.0310(5) Uani 1 1 d . . . S11 S 0.55797(7) 0.34760(7) 0.39797(7) 0.0414(2) Uani 1 1 d . . . S12 S 0.71299(7) 0.31702(5) 0.30939(6) 0.0340(2) Uani 1 1 d . . . N11 N 0.5976(2) 0.32922(18) 0.2996(2) 0.0375(7) Uani 1 1 d . . . C11 C 0.6755(3) 0.3581(3) 0.5800(3) 0.0471(10) Uani 1 1 d . . . C12 C 0.6657(2) 0.3457(2) 0.4743(2) 0.0327(8) Uani 1 1 d . . . C13 C 0.7438(2) 0.32981(19) 0.4298(2) 0.0271(7) Uani 1 1 d . . . C14 C 0.8454(3) 0.3258(2) 0.4838(2) 0.0303(8) Uani 1 1 d . . . C15 C 0.9473(3) 0.3399(2) 0.6442(3) 0.0407(9) Uani 1 1 d . . . C16 C 0.9604(3) 0.3550(3) 0.7419(3) 0.0491(10) Uani 1 1 d . . . C17 C 0.8811(3) 0.3749(3) 0.7864(3) 0.0462(10) Uani 1 1 d . . . C18 C 0.7896(3) 0.3774(3) 0.7331(3) 0.0412(9) Uani 1 1 d . . . C19 C 0.7754(3) 0.3607(2) 0.6345(2) 0.0327(8) Uani 1 1 d . . . C20 C 0.8557(2) 0.3424(2) 0.5892(2) 0.0284(7) Uani 1 1 d . . . O11 O 0.6020(2) 0.3628(4) 0.6162(2) 0.1077(16) Uani 1 1 d . . . O12 O 0.91217(18) 0.30943(17) 0.44106(18) 0.0439(6) Uani 1 1 d . . . H5 H 0.199(2) 0.117(2) 0.859(3) 0.029(9) Uiso 1 1 d . . . H6 H 0.041(3) 0.080(3) 0.864(3) 0.062(14) Uiso 1 1 d . . . H7 H -0.067(3) 0.074(2) 0.721(3) 0.039(10) Uiso 1 1 d . . . H8 H -0.018(2) 0.107(2) 0.575(3) 0.026(9) Uiso 1 1 d . . . H15 H 0.996(3) 0.330(3) 0.619(3) 0.045(12) Uiso 1 1 d . . . H16 H 1.020(3) 0.357(2) 0.777(3) 0.042(11) Uiso 1 1 d . . . H17 H 0.895(3) 0.388(2) 0.858(3) 0.044(10) Uiso 1 1 d . . . H18 H 0.741(3) 0.396(2) 0.761(3) 0.043(11) Uiso 1 1 d . . . As1 As 0.70333(2) 0.08320(2) 0.52469(3) 0.03067(12) Uani 1 1 d . . . As2 As 0.23108(3) 0.41615(2) 0.60542(3) 0.03122(12) Uani 1 1 d . . . F1 F 0.6400(2) 0.1438(2) 0.5941(2) 0.0904(10) Uani 1 1 d . . . F2 F 0.7653(2) 0.02444(15) 0.4512(2) 0.0729(8) Uani 1 1 d . . . F3 F 0.75249(19) 0.02022(18) 0.62041(19) 0.0719(8) Uani 1 1 d . . . F4 F 0.61020(17) 0.00955(17) 0.49934(18) 0.0651(7) Uani 1 1 d . . . F5 F 0.65258(17) 0.14587(13) 0.42698(16) 0.0519(6) Uani 1 1 d . . . F6 F 0.79706(16) 0.15612(14) 0.5475(2) 0.0674(8) Uani 1 1 d . . . F7 F 0.31396(16) 0.48877(13) 0.66737(15) 0.0478(6) Uani 1 1 d . . . F8 F 0.15141(15) 0.34214(13) 0.54266(16) 0.0468(5) Uani 1 1 d . . . F9 F 0.21554(19) 0.48596(13) 0.50831(16) 0.0596(7) Uani 1 1 d . . . F10 F 0.32420(16) 0.36562(13) 0.56058(18) 0.0497(6) Uani 1 1 d . . . F11 F 0.24855(19) 0.34565(14) 0.70164(16) 0.0566(6) Uani 1 1 d . . . F12 F 0.13933(19) 0.46852(17) 0.6486(2) 0.0725(8) Uani 1 1 d . . . S20 S 0.47728(7) 0.43653(7) 0.80596(7) 0.0390(2) Uani 1 1 d . . . O21 O 0.5377(2) 0.49820(18) 0.7701(2) 0.0648(9) Uani 1 1 d . . . O22 O 0.4743(2) 0.34912(18) 0.7754(2) 0.0608(8) 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 0.0364(5) 0.0330(4) 0.0209(4) 0.0020(3) 0.0090(4) 0.0003(4) S2 0.0244(4) 0.0368(4) 0.0273(5) 0.0032(4) 0.0088(3) -0.0001(4) N1 0.0362(16) 0.0340(15) 0.0260(15) 0.0021(12) 0.0125(12) 0.0005(13) C1 0.0255(17) 0.0250(16) 0.0282(19) 0.0010(14) 0.0037(15) 0.0004(14) C2 0.0295(17) 0.0156(14) 0.0209(16) 0.0000(12) 0.0070(14) 0.0038(13) C3 0.0233(16) 0.0189(15) 0.0233(17) 0.0004(12) 0.0082(13) 0.0022(12) C4 0.0267(17) 0.0210(15) 0.0204(17) -0.0003(13) 0.0061(14) 0.0012(13) C5 0.035(2) 0.0368(19) 0.028(2) 0.0029(15) 0.0117(17) 0.0002(16) C6 0.043(2) 0.047(2) 0.038(2) 0.0053(18) 0.0215(19) 0.0011(18) C7 0.024(2) 0.056(3) 0.056(3) 0.008(2) 0.0165(19) -0.0008(18) C8 0.0274(19) 0.042(2) 0.039(2) 0.0025(17) 0.0024(17) -0.0007(16) C9 0.0257(17) 0.0232(16) 0.0288(18) -0.0011(13) 0.0074(14) 0.0031(13) C10 0.0253(17) 0.0220(16) 0.0280(18) 0.0002(13) 0.0079(14) 0.0022(13) O1 0.0308(13) 0.0568(16) 0.0277(14) 0.0010(12) -0.0032(11) -0.0016(12) O2 0.0297(13) 0.0408(13) 0.0224(12) 0.0009(10) 0.0041(10) 0.0005(11) S11 0.0325(5) 0.0560(6) 0.0341(5) 0.0006(4) 0.0011(4) -0.0096(4) S12 0.0488(6) 0.0292(4) 0.0235(4) -0.0025(3) 0.0049(4) -0.0003(4) N11 0.0476(19) 0.0336(15) 0.0289(16) 0.0024(13) -0.0007(14) -0.0059(14) C11 0.036(2) 0.077(3) 0.031(2) -0.009(2) 0.0140(17) -0.007(2) C12 0.0298(18) 0.0391(19) 0.0294(19) 0.0025(15) 0.0056(15) -0.0094(16) C13 0.0396(19) 0.0198(15) 0.0226(17) 0.0016(13) 0.0068(15) -0.0054(14) C14 0.036(2) 0.0246(16) 0.0309(19) 0.0028(14) 0.0075(16) -0.0032(15) C15 0.038(2) 0.038(2) 0.044(2) 0.0020(18) 0.0021(19) 0.0008(18) C16 0.051(3) 0.052(2) 0.038(2) -0.0005(19) -0.011(2) -0.002(2) C17 0.068(3) 0.042(2) 0.026(2) 0.0004(17) -0.002(2) -0.010(2) C18 0.054(3) 0.043(2) 0.028(2) -0.0003(17) 0.0125(19) -0.010(2) C19 0.038(2) 0.0349(19) 0.0264(19) -0.0004(15) 0.0078(15) -0.0077(16) C20 0.0354(19) 0.0243(16) 0.0244(17) 0.0029(13) 0.0017(15) -0.0067(14) O11 0.0440(19) 0.236(5) 0.048(2) -0.041(3) 0.0227(16) -0.014(3) O12 0.0385(15) 0.0585(17) 0.0378(15) -0.0049(13) 0.0152(12) 0.0001(13) As1 0.0255(2) 0.0345(2) 0.0328(2) -0.00016(15) 0.00717(15) -0.00211(14) As2 0.0384(2) 0.02309(19) 0.0309(2) -0.00397(14) 0.00210(16) 0.00236(15) F1 0.0713(18) 0.147(3) 0.0566(17) -0.0293(18) 0.0227(14) 0.0400(19) F2 0.098(2) 0.0397(13) 0.097(2) -0.0040(13) 0.0611(17) 0.0124(13) F3 0.0640(17) 0.0810(18) 0.0613(17) 0.0290(14) -0.0170(13) -0.0097(14) F4 0.0508(14) 0.0762(17) 0.0633(16) 0.0235(14) -0.0054(12) -0.0304(13) F5 0.0666(15) 0.0377(12) 0.0466(14) 0.0069(10) -0.0044(11) -0.0045(11) F6 0.0380(13) 0.0355(12) 0.120(2) 0.0029(13) -0.0130(14) -0.0076(10) F7 0.0611(14) 0.0298(10) 0.0453(13) -0.0019(9) -0.0127(11) -0.0034(10) F8 0.0419(12) 0.0392(11) 0.0568(14) -0.0133(10) 0.0004(10) -0.0033(10) F9 0.100(2) 0.0298(11) 0.0399(13) 0.0037(10) -0.0154(13) -0.0023(12) F10 0.0468(13) 0.0355(12) 0.0711(16) -0.0071(11) 0.0229(12) 0.0007(10) F11 0.0898(18) 0.0412(12) 0.0377(13) 0.0066(10) 0.0073(12) -0.0103(12) F12 0.0618(16) 0.0692(17) 0.090(2) -0.0340(15) 0.0233(14) 0.0150(14) S20 0.0382(5) 0.0456(5) 0.0331(5) 0.0021(4) 0.0057(4) 0.0016(4) O21 0.069(2) 0.0440(16) 0.081(2) 0.0143(16) 0.0133(17) -0.0120(15) O22 0.071(2) 0.0412(16) 0.067(2) 0.0061(15) 0.0022(16) -0.0012(15) _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 N1 1.597(3) . ? S1 C2 1.695(3) . ? S2 N1 1.600(3) . ? S2 C3 1.695(3) . ? C1 O1 1.213(4) . ? C1 C9 1.480(4) . ? C1 C2 1.489(4) . ? C2 C3 1.361(4) . ? C3 C4 1.494(4) . ? C4 O2 1.205(4) . ? C4 C10 1.478(4) . ? C5 C6 1.388(5) . ? C5 C10 1.392(5) . ? C5 H5 0.91(3) . ? C6 C7 1.372(6) . ? C6 H6 0.92(5) . ? C7 C8 1.387(6) . ? C7 H7 0.87(4) . ? C8 C9 1.383(5) . ? C8 H8 0.91(3) . ? C9 C10 1.412(4) . ? S11 N11 1.594(3) . ? S11 C12 1.692(3) . ? S12 N11 1.598(3) . ? S12 C13 1.686(3) . ? C11 O11 1.216(5) . ? C11 C19 1.471(5) . ? C11 C12 1.481(5) . ? C12 C13 1.361(5) . ? C13 C14 1.490(5) . ? C14 O12 1.211(4) . ? C14 C20 1.485(5) . ? C15 C16 1.374(6) . ? C15 C20 1.377(5) . ? C15 H15 0.83(4) . ? C16 C17 1.387(6) . ? C16 H16 0.89(4) . ? C17 C18 1.366(6) . ? C17 H17 1.01(4) . ? C18 C19 1.390(5) . ? C18 H18 0.89(4) . ? C19 C20 1.401(5) . ? As1 F1 1.688(2) . ? As1 F3 1.698(2) . ? As1 F6 1.698(2) . ? As1 F2 1.701(2) . ? As1 F4 1.702(2) . ? As1 F5 1.721(2) . ? As2 F12 1.697(2) . ? As2 F11 1.708(2) . ? As2 F10 1.711(2) . ? As2 F9 1.711(2) . ? As2 F8 1.714(2) . ? As2 F7 1.722(2) . ? S20 O22 1.391(3) . ? S20 O21 1.404(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 S1 C2 98.59(15) . . ? N1 S2 C3 98.27(15) . . ? S1 N1 S2 116.11(17) . . ? O1 C1 C9 125.0(3) . . ? O1 C1 C2 119.8(3) . . ? C9 C1 C2 115.2(3) . . ? C3 C2 C1 123.1(3) . . ? C3 C2 S1 113.2(2) . . ? C1 C2 S1 123.7(2) . . ? C2 C3 C4 122.7(3) . . ? C2 C3 S2 113.8(2) . . ? C4 C3 S2 123.5(2) . . ? O2 C4 C10 125.3(3) . . ? O2 C4 C3 119.9(3) . . ? C10 C4 C3 114.8(3) . . ? C6 C5 C10 119.9(4) . . ? C6 C5 H5 120(2) . . ? C10 C5 H5 120(2) . . ? C7 C6 C5 120.4(4) . . ? C7 C6 H6 122(3) . . ? C5 C6 H6 118(3) . . ? C6 C7 C8 120.6(4) . . ? C6 C7 H7 120(3) . . ? C8 C7 H7 119(3) . . ? C9 C8 C7 120.1(4) . . ? C9 C8 H8 116(2) . . ? C7 C8 H8 124(2) . . ? C8 C9 C10 119.7(3) . . ? C8 C9 C1 118.7(3) . . ? C10 C9 C1 121.6(3) . . ? C5 C10 C9 119.4(3) . . ? C5 C10 C4 118.1(3) . . ? C9 C10 C4 122.5(3) . . ? N11 S11 C12 98.61(17) . . ? N11 S12 C13 99.10(16) . . ? S11 N11 S12 115.58(18) . . ? O11 C11 C19 124.6(4) . . ? O11 C11 C12 118.8(4) . . ? C19 C11 C12 116.6(3) . . ? C13 C12 C11 122.3(3) . . ? C13 C12 S11 113.7(3) . . ? C11 C12 S11 124.0(3) . . ? C12 C13 C14 122.4(3) . . ? C12 C13 S12 113.0(3) . . ? C14 C13 S12 124.6(3) . . ? O12 C14 C20 125.0(3) . . ? O12 C14 C13 119.7(3) . . ? C20 C14 C13 115.3(3) . . ? C16 C15 C20 120.9(4) . . ? C16 C15 H15 119(3) . . ? C20 C15 H15 120(3) . . ? C15 C16 C17 120.2(4) . . ? C15 C16 H16 121(3) . . ? C17 C16 H16 118(3) . . ? C18 C17 C16 119.8(4) . . ? C18 C17 H17 123(2) . . ? C16 C17 H17 117(2) . . ? C17 C18 C19 120.5(4) . . ? C17 C18 H18 119(3) . . ? C19 C18 H18 120(3) . . ? C18 C19 C20 119.7(3) . . ? C18 C19 C11 119.3(3) . . ? C20 C19 C11 120.9(3) . . ? C15 C20 C19 118.9(3) . . ? C15 C20 C14 118.8(3) . . ? C19 C20 C14 122.3(3) . . ? F1 As1 F3 91.65(15) . . ? F1 As1 F6 89.72(15) . . ? F3 As1 F6 91.17(13) . . ? F1 As1 F2 177.87(15) . . ? F3 As1 F2 90.49(14) . . ? F6 As1 F2 90.28(14) . . ? F1 As1 F4 91.47(16) . . ? F3 As1 F4 89.43(12) . . ? F6 As1 F4 178.65(14) . . ? F2 As1 F4 88.51(14) . . ? F1 As1 F5 88.63(14) . . ? F3 As1 F5 179.23(12) . . ? F6 As1 F5 89.55(12) . . ? F2 As1 F5 89.24(13) . . ? F4 As1 F5 89.84(11) . . ? F12 As2 F11 91.51(14) . . ? F12 As2 F10 178.65(13) . . ? F11 As2 F10 89.66(12) . . ? F12 As2 F9 89.58(14) . . ? F11 As2 F9 178.90(13) . . ? F10 As2 F9 89.24(12) . . ? F12 As2 F8 91.69(12) . . ? F11 As2 F8 89.61(11) . . ? F10 As2 F8 88.98(10) . . ? F9 As2 F8 90.49(11) . . ? F12 As2 F7 90.03(12) . . ? F11 As2 F7 90.22(10) . . ? F10 As2 F7 89.31(11) . . ? F9 As2 F7 89.65(10) . . ? F8 As2 F7 178.28(11) . . ? O22 S20 O21 120.8(2) . . ? _diffrn_measured_fraction_theta_max 0.959 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 0.959 _refine_diff_density_max 0.609 _refine_diff_density_min -0.595 _refine_diff_density_rms 0.072 # Attachment '- C10H4O2S4.cif' data_jp050145 _database_code_depnum_ccdc_archive 'CCDC 741235' _publ_section_references ; Bruker (1997-2003). SAINT. Version 6.45. Bruker AXS Inc., Madison, Wisconsin, USA. Bruker (1997-1999). SMART. Version 5.054. Bruker AXS Inc., Madison, Wisconsin, USA. Sheldrick, G.M. (1997a). SHELXTL. Version 5.1. Bruker AXS Inc., Madison, Wisconsin, USA. Sheldrick, G.M. (1997b). SHELXL97 & SHELXS97. University of Gottingen, Germany. ; _publ_section_exptl_refinement ; ? ; _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C10 H4 O2 S4' _chemical_formula_sum 'C10 H4 O2 S4' _chemical_formula_weight 284.37 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1 ' _symmetry_int_tables_number 2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.2626(10) _cell_length_b 8.2193(11) _cell_length_c 9.4223(12) _cell_angle_alpha 82.359(2) _cell_angle_beta 79.248(3) _cell_angle_gamma 70.376(2) _cell_volume 518.98(12) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 1552 _cell_measurement_theta_min 3.01 _cell_measurement_theta_max 27.90 _exptl_crystal_description irregular _exptl_crystal_colour red _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.820 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 288 _exptl_absorpt_coefficient_mu 0.890 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.754 _exptl_absorpt_correction_T_max 0.924 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1997a)' _exptl_special_details ; Crystal decay was monitored by repeating the initial 50 frames at the end of the data collection and analyzing duplicate reflections. ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_source_type 'Bruker AXS SMART1000/P4' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 3587 _diffrn_reflns_av_R_equivalents 0.0136 _diffrn_reflns_av_sigmaI/netI 0.0283 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.21 _diffrn_reflns_theta_max 27.50 _reflns_number_total 2245 _reflns_number_gt 1830 _reflns_threshold_expression >2\s(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _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^)+(0.0703P)^2^+0.6773P] 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 2245 _refine_ls_number_parameters 145 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0581 _refine_ls_R_factor_gt 0.0428 _refine_ls_wR_factor_ref 0.1276 _refine_ls_wR_factor_gt 0.1192 _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 S1 S 0.25078(13) 0.48385(10) 0.20196(9) 0.0262(2) Uani 1 1 d . . . S2 S 0.35187(14) 0.43797(11) 0.39518(9) 0.0314(2) Uani 1 1 d . . . S3 S 0.13449(13) 0.63260(11) 0.50569(9) 0.0294(2) Uani 1 1 d . . . S4 S 0.22138(13) 0.83807(11) 0.41186(8) 0.0280(2) Uani 1 1 d . . . C5 C 0.2359(4) 0.8286(4) 0.2253(3) 0.0179(6) Uani 1 1 d . . . C6 C 0.2420(5) 0.9997(4) 0.1534(3) 0.0209(6) Uani 1 1 d . . . C7 C 0.2535(4) 1.0281(4) -0.0062(3) 0.0194(6) Uani 1 1 d . . . C8 C 0.2597(5) 1.1875(4) -0.0754(3) 0.0225(6) Uani 1 1 d . . . H8 H 0.2559 1.2779 -0.0207 0.027 Uiso 1 1 calc R . . C9 C 0.2713(5) 1.2131(4) -0.2261(3) 0.0258(7) Uani 1 1 d . . . H9 H 0.2751 1.3215 -0.2740 0.031 Uiso 1 1 calc R . . C10 C 0.2775(5) 1.0803(4) -0.3055(3) 0.0266(7) Uani 1 1 d . . . H10 H 0.2885 1.0977 -0.4081 0.032 Uiso 1 1 calc R . . C11 C 0.2677(5) 0.9226(4) -0.2371(3) 0.0230(6) Uani 1 1 d . . . H11 H 0.2687 0.8335 -0.2923 0.028 Uiso 1 1 calc R . . C12 C 0.2566(4) 0.8953(4) -0.0869(3) 0.0194(6) Uani 1 1 d . . . C13 C 0.2491(4) 0.7263(4) -0.0142(3) 0.0196(6) Uani 1 1 d . . . C14 C 0.2484(4) 0.6966(4) 0.1463(3) 0.0177(6) Uani 1 1 d . . . O1 O 0.2359(4) 1.1127(3) 0.2282(3) 0.0317(6) Uani 1 1 d . . . O2 O 0.2430(4) 0.6101(3) -0.0805(2) 0.0310(6) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.0366(5) 0.0146(4) 0.0290(4) 0.0013(3) -0.0072(3) -0.0105(3) S2 0.0351(5) 0.0267(4) 0.0292(4) 0.0046(3) -0.0079(3) -0.0065(4) S3 0.0332(5) 0.0301(5) 0.0248(4) 0.0023(3) -0.0020(3) -0.0128(4) S4 0.0381(5) 0.0297(4) 0.0188(4) -0.0024(3) -0.0047(3) -0.0138(4) C5 0.0196(14) 0.0163(14) 0.0182(13) -0.0014(11) -0.0013(11) -0.0071(11) C6 0.0236(15) 0.0161(14) 0.0246(15) -0.0022(12) -0.0045(12) -0.0080(12) C7 0.0222(15) 0.0142(13) 0.0228(15) -0.0013(11) -0.0045(11) -0.0065(11) C8 0.0267(16) 0.0162(14) 0.0264(16) 0.0007(12) -0.0059(12) -0.0092(12) C9 0.0300(17) 0.0205(15) 0.0275(16) 0.0061(12) -0.0068(13) -0.0108(13) C10 0.0283(17) 0.0286(17) 0.0215(15) 0.0049(12) -0.0064(13) -0.0084(14) C11 0.0258(16) 0.0242(16) 0.0191(15) -0.0026(12) -0.0044(12) -0.0072(13) C12 0.0192(14) 0.0172(14) 0.0218(14) -0.0018(11) -0.0046(11) -0.0049(11) C13 0.0210(15) 0.0196(14) 0.0196(14) -0.0025(11) -0.0008(11) -0.0089(12) C14 0.0214(15) 0.0128(13) 0.0194(14) -0.0004(10) -0.0028(11) -0.0065(11) O1 0.0546(16) 0.0183(11) 0.0277(12) -0.0044(9) -0.0105(11) -0.0155(11) O2 0.0510(16) 0.0217(12) 0.0255(12) -0.0063(9) -0.0050(11) -0.0169(11) _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 C14 1.753(3) . ? S1 S2 2.0311(12) . ? S2 S3 2.0661(13) . ? S3 S4 2.0353(12) . ? S4 C5 1.751(3) . ? C5 C14 1.365(4) . ? C5 C6 1.489(4) . ? C6 O1 1.224(4) . ? C6 C7 1.481(4) . ? C7 C8 1.394(4) . ? C7 C12 1.404(4) . ? C8 C9 1.397(4) . ? C8 H8 0.9500 . ? C9 C10 1.388(5) . ? C9 H9 0.9500 . ? C10 C11 1.387(4) . ? C10 H10 0.9500 . ? C11 C12 1.394(4) . ? C11 H11 0.9500 . ? C12 C13 1.478(4) . ? C13 O2 1.226(4) . ? C13 C14 1.499(4) . ? 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 C14 S1 S2 103.35(10) . . ? S1 S2 S3 99.18(5) . . ? S4 S3 S2 98.99(5) . . ? C5 S4 S3 104.99(10) . . ? C14 C5 C6 121.1(3) . . ? C14 C5 S4 131.3(2) . . ? C6 C5 S4 107.5(2) . . ? O1 C6 C7 122.1(3) . . ? O1 C6 C5 118.8(3) . . ? C7 C6 C5 119.0(2) . . ? C8 C7 C12 120.2(3) . . ? C8 C7 C6 119.8(3) . . ? C12 C7 C6 119.9(3) . . ? C7 C8 C9 119.5(3) . . ? C7 C8 H8 120.3 . . ? C9 C8 H8 120.3 . . ? C10 C9 C8 120.0(3) . . ? C10 C9 H9 120.0 . . ? C8 C9 H9 120.0 . . ? C11 C10 C9 120.8(3) . . ? C11 C10 H10 119.6 . . ? C9 C10 H10 119.6 . . ? C10 C11 C12 119.7(3) . . ? C10 C11 H11 120.2 . . ? C12 C11 H11 120.2 . . ? C11 C12 C7 119.8(3) . . ? C11 C12 C13 119.7(3) . . ? C7 C12 C13 120.6(3) . . ? O2 C13 C12 122.3(3) . . ? O2 C13 C14 119.0(3) . . ? C12 C13 C14 118.7(2) . . ? C5 C14 C13 120.4(3) . . ? C5 C14 S1 130.4(2) . . ? C13 C14 S1 109.1(2) . . ? _diffrn_measured_fraction_theta_max 0.938 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 1.381 _refine_diff_density_min -0.427 _refine_diff_density_rms 0.102 data_jp080830 _database_code_depnum_ccdc_archive 'CCDC 741236' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_formula_moiety 'C10 H4 N O2 S2' _chemical_formula_sum 'C10 H4 N O2 S2' _exptl_crystal_recrystallization_method CH3CN _chemical_melting_point ? _exptl_crystal_description Plate _exptl_crystal_colour Green _diffrn_ambient_temperature 198(1) _chemical_formula_weight 234.26 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' N N 0.0061 0.0033 '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 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_int_tables_number 14 _chemical_absolute_configuration ? 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 8.359(2) _cell_length_b 16.770(4) _cell_length_c 7.1478(18) _cell_angle_alpha 90.00 _cell_angle_beta 115.251(3) _cell_angle_gamma 90.00 _cell_volume 906.3(4) _cell_formula_units_Z 4 _cell_measurement_temperature 198(1) _cell_measurement_reflns_used 2179 _cell_measurement_theta_min 2.69 _cell_measurement_theta_max 27.06 _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.717 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 476 _exptl_absorpt_coefficient_mu 0.559 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8964 _exptl_absorpt_correction_T_max 0.9726 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2004)' _exptl_special_details ; Crystal decay was monitored by repeating the initial 50 frames at the end of the data collection and analyzing duplicate reflections. ; _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_source_type K760 _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker AXS SMART1000/P4' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 6168 _diffrn_reflns_av_R_equivalents 0.0268 _diffrn_reflns_av_sigmaI/netI 0.0288 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 2.43 _diffrn_reflns_theta_max 27.47 _reflns_number_total 2017 _reflns_number_gt 1531 _reflns_threshold_expression 'I > 2\s(I)' _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL (Sheldrick, 2008)' _computing_publication_material 'Bruker SHELXTL (Sheldrick, 2008)' _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^)+(0.0343P)^2^+0.7754P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2017 _refine_ls_number_parameters 152 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0608 _refine_ls_R_factor_gt 0.0375 _refine_ls_wR_factor_ref 0.1015 _refine_ls_wR_factor_gt 0.0862 _refine_ls_goodness_of_fit_ref 1.157 _refine_ls_restrained_S_all 1.157 _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 0.37963(9) 0.54798(4) -0.32786(11) 0.0348(2) Uani 1 1 d . . . S2 S 0.65327(9) 0.44385(4) -0.10790(11) 0.03293(19) Uani 1 1 d . . . N1 N 0.4464(3) 0.45472(14) -0.2859(4) 0.0394(6) Uani 1 1 d . . . C1 C 0.5940(3) 0.68208(14) -0.1556(4) 0.0262(5) Uani 1 1 d . . . C2 C 0.5753(3) 0.59443(14) -0.1744(4) 0.0260(5) Uani 1 1 d . . . C3 C 0.7075(3) 0.54368(14) -0.0622(4) 0.0259(5) Uani 1 1 d . . . C4 C 0.8767(3) 0.57138(14) 0.0996(4) 0.0251(5) Uani 1 1 d . . . C5 C 1.0631(3) 0.68944(15) 0.2607(4) 0.0269(5) Uani 1 1 d . . . C6 C 1.0908(4) 0.77061(16) 0.2833(4) 0.0305(6) Uani 1 1 d . . . C7 C 0.9575(4) 0.82293(15) 0.1650(4) 0.0323(6) Uani 1 1 d . . . C8 C 0.7962(4) 0.79351(14) 0.0233(4) 0.0287(6) Uani 1 1 d . . . C9 C 0.7667(3) 0.71196(14) -0.0014(4) 0.0231(5) Uani 1 1 d . . . C10 C 0.9025(3) 0.65898(13) 0.1198(4) 0.0222(5) Uani 1 1 d . . . O1 O 0.4724(2) 0.72539(12) -0.2639(3) 0.0398(5) Uani 1 1 d . . . O2 O 0.9861(2) 0.52351(11) 0.2116(3) 0.0369(5) Uani 1 1 d . . . H5 H 1.150(4) 0.6528(16) 0.343(4) 0.029(7) Uiso 1 1 d . . . H6 H 1.202(4) 0.7901(16) 0.379(4) 0.030(7) Uiso 1 1 d . . . H7 H 0.975(4) 0.8789(19) 0.182(4) 0.043(8) Uiso 1 1 d . . . H8 H 0.706(4) 0.8286(17) -0.057(4) 0.033(7) Uiso 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 0.0268(4) 0.0350(4) 0.0325(4) -0.0007(3) 0.0029(3) -0.0065(3) S2 0.0327(4) 0.0223(3) 0.0433(4) -0.0043(3) 0.0157(3) -0.0023(2) N1 0.0368(13) 0.0321(12) 0.0411(14) -0.0089(10) 0.0088(11) -0.0082(10) C1 0.0237(13) 0.0278(12) 0.0281(13) 0.0048(10) 0.0119(10) 0.0024(10) C2 0.0242(13) 0.0283(13) 0.0229(13) 0.0001(10) 0.0078(10) -0.0023(9) C3 0.0266(13) 0.0221(12) 0.0310(13) -0.0013(10) 0.0142(11) -0.0014(9) C4 0.0241(12) 0.0235(12) 0.0278(13) 0.0032(9) 0.0112(10) 0.0022(9) C5 0.0241(13) 0.0298(13) 0.0256(13) 0.0015(10) 0.0093(10) 0.0011(10) C6 0.0303(14) 0.0320(13) 0.0301(14) -0.0076(11) 0.0137(12) -0.0084(11) C7 0.0437(16) 0.0226(12) 0.0368(15) -0.0037(11) 0.0230(13) -0.0054(11) C8 0.0343(15) 0.0218(12) 0.0324(14) 0.0038(10) 0.0167(12) 0.0038(10) C9 0.0247(12) 0.0240(12) 0.0226(12) 0.0034(9) 0.0120(10) 0.0008(9) C10 0.0234(12) 0.0218(11) 0.0223(12) 0.0012(9) 0.0104(10) 0.0013(9) O1 0.0258(10) 0.0371(10) 0.0463(12) 0.0116(9) 0.0056(9) 0.0075(8) O2 0.0295(10) 0.0268(9) 0.0443(11) 0.0078(8) 0.0058(9) 0.0044(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 N1 1.645(2) . ? S1 C2 1.719(2) . ? S2 N1 1.663(2) . ? S2 C3 1.729(2) . ? C1 O1 1.220(3) . ? C1 C2 1.478(3) . ? C1 C9 1.481(3) . ? C2 C3 1.353(3) . ? C3 C4 1.469(3) . ? C4 O2 1.224(3) . ? C4 C10 1.483(3) . ? C5 C6 1.379(4) . ? C5 C10 1.388(3) . ? C5 H5 0.94(3) . ? C6 C7 1.386(4) . ? C6 H6 0.95(3) . ? C7 C8 1.387(4) . ? C7 H7 0.95(3) . ? C8 C9 1.388(3) . ? C8 H8 0.93(3) . ? C9 C10 1.410(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 S1 C2 99.09(12) . . ? N1 S2 C3 98.13(12) . . ? S1 N1 S2 113.89(13) . . ? O1 C1 C2 120.5(2) . . ? O1 C1 C9 123.7(2) . . ? C2 C1 C9 115.8(2) . . ? C3 C2 C1 122.9(2) . . ? C3 C2 S1 114.03(19) . . ? C1 C2 S1 122.91(18) . . ? C2 C3 C4 122.4(2) . . ? C2 C3 S2 114.54(19) . . ? C4 C3 S2 122.78(18) . . ? O2 C4 C3 120.5(2) . . ? O2 C4 C10 123.3(2) . . ? C3 C4 C10 116.2(2) . . ? C6 C5 C10 120.7(2) . . ? C6 C5 H5 121.6(16) . . ? C10 C5 H5 117.7(16) . . ? C5 C6 C7 120.2(2) . . ? C5 C6 H6 119.4(16) . . ? C7 C6 H6 120.5(16) . . ? C6 C7 C8 119.9(2) . . ? C6 C7 H7 120.5(18) . . ? C8 C7 H7 119.6(18) . . ? C7 C8 C9 120.5(2) . . ? C7 C8 H8 120.0(17) . . ? C9 C8 H8 119.4(17) . . ? C8 C9 C10 119.4(2) . . ? C8 C9 C1 119.5(2) . . ? C10 C9 C1 121.2(2) . . ? C5 C10 C9 119.3(2) . . ? C5 C10 C4 119.4(2) . . ? C9 C10 C4 121.3(2) . . ? _diffrn_measured_fraction_theta_max 0.972 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.413 _refine_diff_density_min -0.261 _refine_diff_density_rms 0.075 data_jp080831 _database_code_depnum_ccdc_archive 'CCDC 741237' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_formula_moiety 'C10 H4 N O2 S2' _chemical_formula_sum 'C10 H4 N O2 S2' _exptl_crystal_recrystallization_method CH3CN _chemical_melting_point ? _exptl_crystal_description Plate _exptl_crystal_colour Green _diffrn_ambient_temperature 296(1) _chemical_formula_weight 234.26 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' N N 0.0061 0.0033 '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 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc ' _symmetry_int_tables_number 14 _chemical_absolute_configuration ? 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 8.397(2) _cell_length_b 16.782(4) _cell_length_c 7.2137(19) _cell_angle_alpha 90.00 _cell_angle_beta 115.023(3) _cell_angle_gamma 90.00 _cell_volume 921.1(4) _cell_formula_units_Z 4 _cell_measurement_temperature 296(1) _cell_measurement_reflns_used 1704 _cell_measurement_theta_min 2.68 _cell_measurement_theta_max 25.66 _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.689 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 476 _exptl_absorpt_coefficient_mu 0.550 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8980 _exptl_absorpt_correction_T_max 0.9730 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2004)' _exptl_special_details ; Crystal decay was monitored by repeating the initial 50 frames at the end of the data collection and analyzing duplicate reflections. ; _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_source_type K760 _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker AXS SMART1000/P4' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 6266 _diffrn_reflns_av_R_equivalents 0.0328 _diffrn_reflns_av_sigmaI/netI 0.0352 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 2.43 _diffrn_reflns_theta_max 27.49 _reflns_number_total 2045 _reflns_number_gt 1338 _reflns_threshold_expression 'I > 2\s(I)' _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL (Sheldrick, 2008)' _computing_publication_material 'Bruker SHELXTL (Sheldrick, 2008)' _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^)+(0.0352P)^2^+0.7877P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2045 _refine_ls_number_parameters 152 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0839 _refine_ls_R_factor_gt 0.0418 _refine_ls_wR_factor_ref 0.1191 _refine_ls_wR_factor_gt 0.0906 _refine_ls_goodness_of_fit_ref 1.137 _refine_ls_restrained_S_all 1.137 _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 1.11930(11) 0.95276(5) 0.79122(15) 0.0561(3) Uani 1 1 d . . . S2 S 0.84741(11) 1.05634(5) 0.74018(14) 0.0530(3) Uani 1 1 d . . . N1 N 1.0520(4) 1.04576(17) 0.7676(5) 0.0621(8) Uani 1 1 d . . . C1 C 0.9072(4) 0.81885(17) 0.7518(5) 0.0404(7) Uani 1 1 d . . . C2 C 0.9253(4) 0.90635(17) 0.7512(5) 0.0403(7) Uani 1 1 d . . . C3 C 0.7931(4) 0.95668(16) 0.7317(5) 0.0388(7) Uani 1 1 d . . . C4 C 0.6253(4) 0.92906(17) 0.7239(5) 0.0393(7) Uani 1 1 d . . . C5 C 0.4400(4) 0.81079(19) 0.6984(5) 0.0427(7) Uani 1 1 d . . . C6 C 0.4124(5) 0.7300(2) 0.6930(5) 0.0485(8) Uani 1 1 d . . . C7 C 0.5453(5) 0.67839(19) 0.7084(5) 0.0502(8) Uani 1 1 d . . . C8 C 0.7056(5) 0.70726(18) 0.7285(5) 0.0452(8) Uani 1 1 d . . . C9 C 0.7347(4) 0.78896(16) 0.7328(4) 0.0359(6) Uani 1 1 d . . . C10 C 0.5998(4) 0.84146(16) 0.7183(4) 0.0355(6) Uani 1 1 d . . . O1 O 1.0280(3) 0.77566(14) 0.7653(4) 0.0625(7) Uani 1 1 d . . . O2 O 0.5156(3) 0.97656(13) 0.7250(4) 0.0585(7) Uani 1 1 d . . . H1 H 0.352(4) 0.8470(18) 0.692(4) 0.043(8) Uiso 1 1 d . . . H2 H 0.300(4) 0.7107(18) 0.676(4) 0.044(8) Uiso 1 1 d . . . H3 H 0.533(4) 0.622(2) 0.716(5) 0.054(9) Uiso 1 1 d . . . H4 H 0.799(4) 0.674(2) 0.746(5) 0.059(10) Uiso 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 0.0427(5) 0.0559(5) 0.0772(7) -0.0064(5) 0.0324(5) -0.0094(4) S2 0.0530(5) 0.0350(4) 0.0660(6) 0.0044(4) 0.0202(4) -0.0035(3) N1 0.0562(18) 0.0511(17) 0.082(2) 0.0041(15) 0.0317(17) -0.0134(13) C1 0.0376(16) 0.0398(16) 0.0423(18) -0.0046(13) 0.0153(14) 0.0031(12) C2 0.0380(16) 0.0412(16) 0.0430(18) -0.0027(13) 0.0182(14) -0.0019(12) C3 0.0395(16) 0.0330(14) 0.0422(17) 0.0007(13) 0.0156(13) -0.0019(12) C4 0.0373(16) 0.0358(15) 0.0432(17) -0.0022(13) 0.0155(14) 0.0035(12) C5 0.0402(17) 0.0457(18) 0.0443(19) -0.0006(14) 0.0198(15) 0.0006(14) C6 0.0449(19) 0.0511(19) 0.049(2) 0.0006(15) 0.0187(16) -0.0131(15) C7 0.066(2) 0.0348(17) 0.047(2) -0.0010(14) 0.0211(17) -0.0101(16) C8 0.052(2) 0.0352(16) 0.046(2) -0.0005(14) 0.0181(16) 0.0039(14) C9 0.0377(16) 0.0345(15) 0.0341(16) -0.0027(12) 0.0139(13) 0.0029(12) C10 0.0355(15) 0.0334(14) 0.0379(16) -0.0011(12) 0.0158(13) 0.0004(11) O1 0.0408(13) 0.0545(14) 0.0928(19) -0.0066(13) 0.0289(13) 0.0129(11) O2 0.0450(13) 0.0411(12) 0.0921(19) -0.0046(12) 0.0316(13) 0.0092(10) _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 N1 1.644(3) . ? S1 C2 1.716(3) . ? S2 N1 1.653(3) . ? S2 C3 1.728(3) . ? C1 O1 1.217(3) . ? C1 C2 1.476(4) . ? C1 C9 1.483(4) . ? C2 C3 1.354(4) . ? C3 C4 1.462(4) . ? C4 O2 1.221(3) . ? C4 C10 1.484(4) . ? C5 C6 1.374(4) . ? C5 C10 1.387(4) . ? C5 H1 0.94(3) . ? C6 C7 1.379(5) . ? C6 H2 0.95(3) . ? C7 C8 1.379(5) . ? C7 H3 0.96(3) . ? C8 C9 1.391(4) . ? C8 H4 0.93(3) . ? C9 C10 1.403(4) . ? 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 N1 S1 C2 98.81(14) . . ? N1 S2 C3 98.36(14) . . ? S1 N1 S2 114.11(16) . . ? O1 C1 C2 120.6(3) . . ? O1 C1 C9 123.7(3) . . ? C2 C1 C9 115.7(2) . . ? C3 C2 C1 122.7(3) . . ? C3 C2 S1 114.4(2) . . ? C1 C2 S1 122.9(2) . . ? C2 C3 C4 122.7(3) . . ? C2 C3 S2 114.1(2) . . ? C4 C3 S2 123.0(2) . . ? O2 C4 C3 120.7(3) . . ? O2 C4 C10 123.1(3) . . ? C3 C4 C10 116.2(2) . . ? C6 C5 C10 120.9(3) . . ? C6 C5 H1 121.1(18) . . ? C10 C5 H1 117.9(18) . . ? C5 C6 C7 119.7(3) . . ? C5 C6 H2 119.0(18) . . ? C7 C6 H2 121.3(18) . . ? C8 C7 C6 120.6(3) . . ? C8 C7 H3 117.8(19) . . ? C6 C7 H3 121.5(19) . . ? C7 C8 C9 120.2(3) . . ? C7 C8 H4 123(2) . . ? C9 C8 H4 117(2) . . ? C8 C9 C10 119.3(3) . . ? C8 C9 C1 119.4(3) . . ? C10 C9 C1 121.3(3) . . ? C5 C10 C9 119.3(3) . . ? C5 C10 C4 119.5(3) . . ? C9 C10 C4 121.2(3) . . ? _diffrn_measured_fraction_theta_max 0.970 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.287 _refine_diff_density_min -0.261 _refine_diff_density_rms 0.062