# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2007 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'Tomas Torroba' _publ_contact_author_address ;Department of Chemistry Faculty of Science University of Burgos 09001 Burgos, SPAIN ; _publ_contact_author_email ttorroba@ubu.es _publ_contact_author_phone +34947258088 _publ_contact_author_fax +34947258831 loop_ _publ_author_name _publ_author_address A.M.Granados ;Instituto de Investigaciones en Fisicoquimica de Cordoba (INFIQC) Departamento de Quimica Organica Facultad de Ciencias Quimicas Universidad Nacional de Cordoba X5000HUA Cordoba, Argentina Fax: 54 351 4333030 Tel: 54 351 4334170; E-mail: ale@dqo.fcq.unc.edu.ar ; A.M.Fracaroli ;Instituto de Investigaciones en Fisicoquimica de Cordoba (INFIQC) Departamento de Quimica Organica Facultad de Ciencias Quimicas Universidad Nacional de Cordoba X5000HUA Cordoba, Argentina ; 'R.H.de Rossi' ;Instituto de Investigaciones en Fisicoquimica de Cordoba (INFIQC) Departamento de Quimica Organica Facultad de Ciencias Quimicas Universidad Nacional de Cordoba X5000HUA Cordoba, Argentina ; P.Fuertes ;Chemistry Department Faculty of Science University of Burgos 09001 Burgos, Spain ; T.Torroba ;Chemistry Department Faculty of Science University of Burgos 09001 Burgos, Spain ; _publ_section_title ; Alkynyl Fischer Carbene Complex as a Traceless Directing Group for the Regioselective Cycloaddition of Dithiolethiones to Arylacetylene: Synthesis of E-Dithiafulvene Thione and Dithioesters ; data_1 _database_code_depnum_ccdc_archive 'CCDC 664202' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C9 H4 Cr O5 S3' _chemical_formula_sum 'C9 H4 Cr O5 S3' _chemical_formula_weight 340.30 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' 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' Cr Cr 0.3209 0.6236 '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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/c _symmetry_space_group_name_Hall '-C 2yc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 23.944(3) _cell_length_b 7.6413(10) _cell_length_c 28.506(4) _cell_angle_alpha 90.00 _cell_angle_beta 105.663(2) _cell_angle_gamma 90.00 _cell_volume 5022.0(11) _cell_formula_units_Z 16 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1174 _cell_measurement_theta_min 3.06 _cell_measurement_theta_max 18.79 _exptl_crystal_description plate _exptl_crystal_colour green _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.800 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2720 _exptl_absorpt_coefficient_mu 1.416 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.508 _exptl_absorpt_correction_T_max 0.972 _exptl_absorpt_process_details 'SADABS(Sheldrick, 2001)' _exptl_special_details ; ? ; _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 'CCD area detector' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 23664 _diffrn_reflns_av_R_equivalents 0.1013 _diffrn_reflns_av_sigmaI/netI 0.0745 _diffrn_reflns_limit_h_min -28 _diffrn_reflns_limit_h_max 28 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -33 _diffrn_reflns_limit_l_max 33 _diffrn_reflns_theta_min 1.48 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4407 _reflns_number_gt 3066 _reflns_threshold_expression >2sigma(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^)+(0.0919P)^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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4407 _refine_ls_number_parameters 327 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0840 _refine_ls_R_factor_gt 0.0507 _refine_ls_wR_factor_ref 0.1679 _refine_ls_wR_factor_gt 0.1284 _refine_ls_goodness_of_fit_ref 1.007 _refine_ls_restrained_S_all 1.007 _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 Cr1 Cr 0.62685(4) 1.01212(11) 0.56775(3) 0.0197(3) Uani 1 1 d . . . S1 S 0.56527(6) 0.99720(19) 0.48488(5) 0.0238(4) Uani 1 1 d . . . S2 S 0.67250(6) 1.0395(2) 0.45245(5) 0.0253(4) Uani 1 1 d . . . S3 S 0.67663(7) 1.0191(2) 0.38143(5) 0.0286(4) Uani 1 1 d . . . O1 O 0.70957(19) 0.7254(5) 0.55502(15) 0.0371(11) Uani 1 1 d . . . O2 O 0.71021(18) 1.2998(5) 0.55736(15) 0.0356(11) Uani 1 1 d . . . O3 O 0.6863(2) 1.0135(6) 0.67556(16) 0.0474(13) Uani 1 1 d . . . O4 O 0.54655(19) 1.3020(6) 0.58447(16) 0.0394(11) Uani 1 1 d . . . O5 O 0.54917(19) 0.7159(6) 0.58555(15) 0.0370(11) Uani 1 1 d . . . C1 C 0.6780(2) 0.8351(7) 0.55827(19) 0.0234(13) Uani 1 1 d . . . C2 C 0.6783(2) 1.1902(8) 0.55972(19) 0.0250(14) Uani 1 1 d . . . C3 C 0.6639(3) 1.0126(7) 0.6345(2) 0.0300(15) Uani 1 1 d . . . C4 C 0.5754(2) 1.1927(8) 0.57808(19) 0.0243(13) Uani 1 1 d . . . C5 C 0.5770(2) 0.8290(8) 0.57880(18) 0.0228(13) Uani 1 1 d . . . C6 C 0.5992(3) 0.9993(7) 0.4403(2) 0.0240(13) Uani 1 1 d . . . C7 C 0.5714(3) 0.9697(7) 0.39040(19) 0.0224(13) Uani 1 1 d . . . H7 H 0.5318 0.9471 0.3801 0.027 Uiso 1 1 calc R . . C8 C 0.6041(3) 0.9752(7) 0.3575(2) 0.0224(13) Uani 1 1 d . . . C9 C 0.5828(3) 0.9439(7) 0.3040(2) 0.0285(14) Uani 1 1 d . . . H9A H 0.5770 0.8207 0.2979 0.043 Uiso 1 1 calc R . . H9B H 0.6109 0.9862 0.2882 0.043 Uiso 1 1 calc R . . H9C H 0.5467 1.0045 0.2913 0.043 Uiso 1 1 calc R . . Cr2 Cr 0.87352(4) 0.95235(12) 0.26376(3) 0.0208(3) Uani 1 1 d . . . S4 S 0.93071(6) 0.9236(2) 0.20642(5) 0.0252(4) Uani 1 1 d . . . S5 S 0.82608(7) 1.0194(2) 0.12774(5) 0.0298(4) Uani 1 1 d . . . S6 S 0.82397(7) 1.0489(2) 0.05554(5) 0.0314(4) Uani 1 1 d . . . O6 O 0.96161(19) 1.2284(6) 0.31385(15) 0.0428(12) Uani 1 1 d . . . O7 O 0.94695(18) 0.6477(6) 0.31456(15) 0.0392(11) Uani 1 1 d . . . O8 O 0.8224(2) 0.9641(6) 0.34923(16) 0.0424(12) Uani 1 1 d . . . O9 O 0.78300(18) 0.6852(6) 0.21176(15) 0.0395(11) Uani 1 1 d . . . O10 O 0.7950(2) 1.2577(6) 0.22017(15) 0.0398(12) Uani 1 1 d . . . C10 C 0.9296(3) 1.1223(8) 0.29546(19) 0.0284(14) Uani 1 1 d . . . C11 C 0.9196(2) 0.7638(8) 0.29537(19) 0.0253(14) Uani 1 1 d . . . C12 C 0.8405(3) 0.9589(8) 0.3155(2) 0.0294(15) Uani 1 1 d . . . C13 C 0.8164(2) 0.7860(8) 0.2308(2) 0.0240(13) Uani 1 1 d . . . C14 C 0.8244(2) 1.1410(8) 0.23420(19) 0.0225(13) Uani 1 1 d . . . C15 C 0.8978(3) 0.9624(6) 0.1476(2) 0.0218(13) Uani 1 1 d . . . C16 C 0.9267(3) 0.9536(7) 0.1099(2) 0.0260(14) Uani 1 1 d . . . H16 H 0.9655 0.9216 0.1168 0.031 Uiso 1 1 calc R . . C17 C 0.8956(2) 0.9933(7) 0.0638(2) 0.0213(13) Uani 1 1 d . . . C18 C 0.9178(3) 0.9982(8) 0.0194(2) 0.0333(16) Uani 1 1 d . . . H18A H 0.9593 1.0082 0.0292 0.050 Uiso 1 1 calc R . . H18B H 0.9015 1.0970 -0.0003 0.050 Uiso 1 1 calc R . . H18C H 0.9069 0.8925 0.0011 0.050 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cr1 0.0177(5) 0.0223(5) 0.0183(5) -0.0002(4) 0.0032(4) -0.0025(4) S1 0.0170(8) 0.0351(9) 0.0191(7) -0.0014(6) 0.0043(6) -0.0011(6) S2 0.0200(8) 0.0349(9) 0.0197(7) -0.0009(6) 0.0031(6) -0.0042(7) S3 0.0244(8) 0.0404(10) 0.0219(8) -0.0002(7) 0.0080(6) -0.0036(7) O1 0.034(3) 0.034(3) 0.045(3) 0.003(2) 0.014(2) 0.008(2) O2 0.028(3) 0.035(3) 0.044(3) 0.000(2) 0.009(2) -0.014(2) O3 0.053(3) 0.062(3) 0.021(3) -0.002(2) -0.001(2) -0.011(3) O4 0.042(3) 0.033(3) 0.047(3) -0.003(2) 0.018(2) 0.010(2) O5 0.037(3) 0.034(3) 0.041(3) 0.003(2) 0.013(2) -0.012(2) C1 0.023(3) 0.025(3) 0.020(3) 0.003(2) 0.002(3) -0.005(3) C2 0.026(3) 0.026(3) 0.019(3) -0.005(2) 0.000(3) -0.002(3) C3 0.024(3) 0.029(4) 0.035(4) 0.001(3) 0.004(3) -0.002(3) C4 0.023(3) 0.031(4) 0.018(3) 0.001(3) 0.002(2) -0.011(3) C5 0.020(3) 0.035(4) 0.013(3) -0.005(3) 0.005(2) 0.004(3) C6 0.032(4) 0.018(3) 0.020(3) 0.005(2) 0.004(3) 0.001(3) C7 0.022(3) 0.021(3) 0.020(3) -0.002(2) -0.002(2) -0.003(2) C8 0.029(3) 0.019(3) 0.019(3) 0.001(2) 0.005(3) 0.001(3) C9 0.036(4) 0.027(3) 0.020(3) -0.003(3) 0.003(3) -0.003(3) Cr2 0.0190(5) 0.0245(5) 0.0187(5) 0.0005(4) 0.0048(4) 0.0006(4) S4 0.0223(8) 0.0330(9) 0.0199(7) 0.0022(6) 0.0048(6) 0.0039(7) S5 0.0237(8) 0.0420(10) 0.0231(8) 0.0017(7) 0.0057(6) 0.0050(7) S6 0.0276(9) 0.0408(10) 0.0238(8) 0.0022(7) 0.0036(7) 0.0089(7) O6 0.037(3) 0.048(3) 0.041(3) -0.015(2) 0.006(2) -0.011(2) O7 0.038(3) 0.043(3) 0.036(3) 0.008(2) 0.010(2) 0.015(2) O8 0.044(3) 0.057(3) 0.030(3) 0.003(2) 0.017(2) 0.007(2) O9 0.034(3) 0.042(3) 0.040(3) -0.008(2) 0.006(2) -0.008(2) O10 0.047(3) 0.037(3) 0.037(3) 0.007(2) 0.014(2) 0.012(2) C10 0.037(4) 0.031(4) 0.017(3) 0.000(3) 0.006(3) 0.008(3) C11 0.023(3) 0.035(4) 0.019(3) -0.002(3) 0.006(3) -0.001(3) C12 0.029(4) 0.035(4) 0.025(3) 0.003(3) 0.009(3) 0.004(3) C13 0.019(3) 0.033(3) 0.024(3) -0.005(3) 0.012(3) -0.002(3) C14 0.020(3) 0.031(3) 0.018(3) 0.000(3) 0.008(2) -0.002(3) C15 0.029(3) 0.011(3) 0.025(3) 0.004(2) 0.007(3) 0.001(2) C16 0.026(3) 0.026(3) 0.023(3) 0.002(3) 0.002(3) 0.000(3) C17 0.023(3) 0.019(3) 0.022(3) -0.004(2) 0.007(2) 0.000(2) C18 0.037(4) 0.037(4) 0.026(3) 0.001(3) 0.008(3) 0.005(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 Cr1 C3 1.871(6) . ? Cr1 C2 1.890(6) . ? Cr1 C1 1.893(6) . ? Cr1 C5 1.920(6) . ? Cr1 C4 1.925(6) . ? Cr1 S1 2.4261(16) . ? S1 C6 1.683(6) . ? S2 C6 1.722(6) . ? S2 S3 2.059(2) . ? S3 C8 1.718(6) . ? O1 C1 1.149(6) . ? O2 C2 1.148(6) . ? O3 C3 1.147(7) . ? O4 C4 1.129(7) . ? O5 C5 1.139(7) . ? C6 C7 1.416(8) . ? C7 C8 1.375(8) . ? C7 H7 0.9300 . ? C8 C9 1.493(7) . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? Cr2 C12 1.853(6) . ? Cr2 C11 1.889(6) . ? Cr2 C14 1.907(6) . ? Cr2 C10 1.912(7) . ? Cr2 C13 1.917(6) . ? Cr2 S4 2.4091(17) . ? S4 C15 1.675(6) . ? S5 C15 1.712(6) . ? S5 S6 2.058(2) . ? S6 C17 1.722(6) . ? O6 C10 1.140(7) . ? O7 C11 1.150(7) . ? O8 C12 1.157(7) . ? O9 C13 1.138(6) . ? O10 C14 1.140(6) . ? C15 C16 1.428(8) . ? C16 C17 1.359(8) . ? C16 H16 0.9300 . ? C17 C18 1.498(8) . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? 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 C3 Cr1 C2 88.7(2) . . ? C3 Cr1 C1 90.0(2) . . ? C2 Cr1 C1 91.7(3) . . ? C3 Cr1 C5 88.8(2) . . ? C2 Cr1 C5 177.4(2) . . ? C1 Cr1 C5 87.6(2) . . ? C3 Cr1 C4 89.4(2) . . ? C2 Cr1 C4 88.1(2) . . ? C1 Cr1 C4 179.4(2) . . ? C5 Cr1 C4 92.6(2) . . ? C3 Cr1 S1 170.9(2) . . ? C2 Cr1 S1 99.23(17) . . ? C1 Cr1 S1 94.25(16) . . ? C5 Cr1 S1 83.35(16) . . ? C4 Cr1 S1 86.38(16) . . ? C6 S1 Cr1 116.4(2) . . ? C6 S2 S3 96.1(2) . . ? C8 S3 S2 95.4(2) . . ? O1 C1 Cr1 176.4(5) . . ? O2 C2 Cr1 176.5(5) . . ? O3 C3 Cr1 179.6(6) . . ? O4 C4 Cr1 178.0(5) . . ? O5 C5 Cr1 177.3(5) . . ? C7 C6 S1 124.4(5) . . ? C7 C6 S2 114.0(4) . . ? S1 C6 S2 121.5(3) . . ? C8 C7 C6 118.7(5) . . ? C8 C7 H7 120.6 . . ? C6 C7 H7 120.6 . . ? C7 C8 C9 126.3(5) . . ? C7 C8 S3 115.8(4) . . ? C9 C8 S3 117.9(4) . . ? C8 C9 H9A 109.5 . . ? C8 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C8 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C12 Cr2 C11 87.8(2) . . ? C12 Cr2 C14 89.2(2) . . ? C11 Cr2 C14 176.9(2) . . ? C12 Cr2 C10 90.1(3) . . ? C11 Cr2 C10 92.7(3) . . ? C14 Cr2 C10 88.0(2) . . ? C12 Cr2 C13 90.4(3) . . ? C11 Cr2 C13 88.6(2) . . ? C14 Cr2 C13 90.7(3) . . ? C10 Cr2 C13 178.6(3) . . ? C12 Cr2 S4 170.21(19) . . ? C11 Cr2 S4 83.57(17) . . ? C14 Cr2 S4 99.48(16) . . ? C10 Cr2 S4 85.80(17) . . ? C13 Cr2 S4 93.88(17) . . ? C15 S4 Cr2 117.5(2) . . ? C15 S5 S6 96.4(2) . . ? C17 S6 S5 94.7(2) . . ? O6 C10 Cr2 177.5(6) . . ? O7 C11 Cr2 179.0(5) . . ? O8 C12 Cr2 176.9(6) . . ? O9 C13 Cr2 178.9(6) . . ? O10 C14 Cr2 174.5(5) . . ? C16 C15 S4 123.5(4) . . ? C16 C15 S5 114.2(4) . . ? S4 C15 S5 122.4(3) . . ? C17 C16 C15 117.9(5) . . ? C17 C16 H16 121.0 . . ? C15 C16 H16 121.0 . . ? C16 C17 C18 126.6(5) . . ? C16 C17 S6 116.9(5) . . ? C18 C17 S6 116.5(4) . . ? C17 C18 H18A 109.5 . . ? C17 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C17 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C3 Cr1 S1 C6 -165.5(12) . . . . ? C2 Cr1 S1 C6 44.3(3) . . . . ? C1 Cr1 S1 C6 -48.1(3) . . . . ? C5 Cr1 S1 C6 -135.1(3) . . . . ? C4 Cr1 S1 C6 131.8(3) . . . . ? C6 S2 S3 C8 -0.1(3) . . . . ? C3 Cr1 C1 O1 22(8) . . . . ? C2 Cr1 C1 O1 111(8) . . . . ? C5 Cr1 C1 O1 -66(8) . . . . ? C4 Cr1 C1 O1 40(28) . . . . ? S1 Cr1 C1 O1 -150(8) . . . . ? C3 Cr1 C2 O2 -15(9) . . . . ? C1 Cr1 C2 O2 -105(9) . . . . ? C5 Cr1 C2 O2 -32(12) . . . . ? C4 Cr1 C2 O2 74(9) . . . . ? S1 Cr1 C2 O2 160(9) . . . . ? C2 Cr1 C3 O3 100(100) . . . . ? C1 Cr1 C3 O3 -168(100) . . . . ? C5 Cr1 C3 O3 -81(100) . . . . ? C4 Cr1 C3 O3 12(100) . . . . ? S1 Cr1 C3 O3 -50(100) . . . . ? C3 Cr1 C4 O4 68(14) . . . . ? C2 Cr1 C4 O4 -21(14) . . . . ? C1 Cr1 C4 O4 51(32) . . . . ? C5 Cr1 C4 O4 157(14) . . . . ? S1 Cr1 C4 O4 -120(14) . . . . ? C3 Cr1 C5 O5 -76(10) . . . . ? C2 Cr1 C5 O5 -60(13) . . . . ? C1 Cr1 C5 O5 14(10) . . . . ? C4 Cr1 C5 O5 -165(10) . . . . ? S1 Cr1 C5 O5 109(10) . . . . ? Cr1 S1 C6 C7 171.8(4) . . . . ? Cr1 S1 C6 S2 -8.5(4) . . . . ? S3 S2 C6 C7 0.0(4) . . . . ? S3 S2 C6 S1 -179.8(3) . . . . ? S1 C6 C7 C8 179.9(4) . . . . ? S2 C6 C7 C8 0.1(7) . . . . ? C6 C7 C8 C9 178.7(5) . . . . ? C6 C7 C8 S3 -0.2(7) . . . . ? S2 S3 C8 C7 0.2(4) . . . . ? S2 S3 C8 C9 -178.8(4) . . . . ? C12 Cr2 S4 C15 172.7(11) . . . . ? C11 Cr2 S4 C15 144.9(3) . . . . ? C14 Cr2 S4 C15 -34.6(3) . . . . ? C10 Cr2 S4 C15 -121.9(3) . . . . ? C13 Cr2 S4 C15 56.7(3) . . . . ? C15 S5 S6 C17 0.8(3) . . . . ? C12 Cr2 C10 O6 -78(12) . . . . ? C11 Cr2 C10 O6 -165(12) . . . . ? C14 Cr2 C10 O6 12(12) . . . . ? C13 Cr2 C10 O6 34(19) . . . . ? S4 Cr2 C10 O6 111(12) . . . . ? C12 Cr2 C11 O7 61(29) . . . . ? C14 Cr2 C11 O7 47(30) . . . . ? C10 Cr2 C11 O7 151(29) . . . . ? C13 Cr2 C11 O7 -30(29) . . . . ? S4 Cr2 C11 O7 -124(29) . . . . ? C11 Cr2 C12 O8 58(10) . . . . ? C14 Cr2 C12 O8 -123(10) . . . . ? C10 Cr2 C12 O8 -35(10) . . . . ? C13 Cr2 C12 O8 146(10) . . . . ? S4 Cr2 C12 O8 30(11) . . . . ? C12 Cr2 C13 O9 -73(29) . . . . ? C11 Cr2 C13 O9 15(29) . . . . ? C14 Cr2 C13 O9 -162(100) . . . . ? C10 Cr2 C13 O9 175(100) . . . . ? S4 Cr2 C13 O9 98(29) . . . . ? C12 Cr2 C14 O10 27(5) . . . . ? C11 Cr2 C14 O10 40(9) . . . . ? C10 Cr2 C14 O10 -63(5) . . . . ? C13 Cr2 C14 O10 117(5) . . . . ? S4 Cr2 C14 O10 -149(5) . . . . ? Cr2 S4 C15 C16 178.7(4) . . . . ? Cr2 S4 C15 S5 -0.4(4) . . . . ? S6 S5 C15 C16 -1.2(4) . . . . ? S6 S5 C15 S4 178.0(3) . . . . ? S4 C15 C16 C17 -177.9(4) . . . . ? S5 C15 C16 C17 1.2(7) . . . . ? C15 C16 C17 C18 177.8(5) . . . . ? C15 C16 C17 S6 -0.5(7) . . . . ? S5 S6 C17 C16 -0.3(4) . . . . ? S5 S6 C17 C18 -178.8(4) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.534 _refine_diff_density_min -0.533 _refine_diff_density_rms 0.128 # Attachment 'Prod3aChemCom.cif' data_2 _database_code_depnum_ccdc_archive 'CCDC 664203' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C23 H18 Cr O6 S4' _chemical_formula_sum 'C23 H18 Cr O6 S4' _chemical_formula_weight 570.61 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' Cr Cr 0.3209 0.6236 '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' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.668(3) _cell_length_b 9.884(3) _cell_length_c 19.498(7) _cell_angle_alpha 100.190(8) _cell_angle_beta 90.645(7) _cell_angle_gamma 97.238(8) _cell_volume 1254.0(8) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 467 _cell_measurement_theta_min 2.19 _cell_measurement_theta_max 14.53 _exptl_crystal_description plate _exptl_crystal_colour orange _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.511 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 584 _exptl_absorpt_coefficient_mu 0.826 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.868 _exptl_absorpt_correction_T_max 0.980 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2001)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 'CCD area detector' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 12132 _diffrn_reflns_av_R_equivalents 0.1389 _diffrn_reflns_av_sigmaI/netI 0.1887 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.53 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4368 _reflns_number_gt 2358 _reflns_threshold_expression >2sigma(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^)+(0.0442P)^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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4368 _refine_ls_number_parameters 308 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1575 _refine_ls_R_factor_gt 0.0798 _refine_ls_wR_factor_ref 0.1650 _refine_ls_wR_factor_gt 0.1382 _refine_ls_goodness_of_fit_ref 0.968 _refine_ls_restrained_S_all 0.968 _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 Cr1 Cr 0.26608(17) 0.52713(12) 0.64136(6) 0.0230(3) Uani 1 1 d . . . S1 S 0.3548(3) 0.7223(2) 0.85069(10) 0.0240(5) Uani 1 1 d . . . S2 S 0.5265(3) 0.9915(2) 0.81808(10) 0.0257(5) Uani 1 1 d . . . S3 S 0.5197(3) 0.6652(2) 0.97830(11) 0.0368(6) Uani 1 1 d . . . S4 S 0.8367(3) 0.8886(2) 1.05354(10) 0.0292(5) Uani 1 1 d . . . O1 O 0.4560(9) 0.3796(6) 0.7465(3) 0.0500(17) Uani 1 1 d . . . O2 O -0.1228(8) 0.3221(6) 0.6302(3) 0.0467(17) Uani 1 1 d . . . O3 O 0.4465(8) 0.3457(6) 0.5200(3) 0.0413(16) Uani 1 1 d . . . O4 O 0.0673(9) 0.6671(6) 0.5358(3) 0.0452(16) Uani 1 1 d . . . O5 O 0.6608(8) 0.7218(6) 0.6446(3) 0.0427(16) Uani 1 1 d . . . O6 O -0.0325(7) 0.6136(5) 0.7424(2) 0.0270(13) Uani 1 1 d . . . C1 C 0.3861(12) 0.4344(8) 0.7072(4) 0.029(2) Uani 1 1 d . . . C2 C 0.0198(12) 0.4004(8) 0.6357(4) 0.031(2) Uani 1 1 d . . . C3 C 0.3772(12) 0.4119(8) 0.5658(4) 0.031(2) Uani 1 1 d . . . C4 C 0.1405(12) 0.6161(8) 0.5756(4) 0.029(2) Uani 1 1 d . . . C5 C 0.5089(10) 0.6529(7) 0.6448(4) 0.0243(18) Uani 1 1 d . . . C6 C 0.1553(10) 0.6454(7) 0.7219(4) 0.0240(18) Uani 1 1 d . . . C7 C -0.1259(10) 0.6970(8) 0.8005(4) 0.033(2) Uani 1 1 d . . . H7A H -0.0981 0.6648 0.8440 0.049 Uiso 1 1 calc R . . H7B H -0.2724 0.6872 0.7916 0.049 Uiso 1 1 calc R . . H7C H -0.0693 0.7947 0.8047 0.049 Uiso 1 1 calc R . . C8 C 0.2812(10) 0.7644(8) 0.7701(4) 0.0223(18) Uani 1 1 d . . . C9 C 0.3587(10) 0.8879(7) 0.7546(4) 0.0237(18) Uani 1 1 d . . . C10 C 0.3126(11) 0.9464(7) 0.6919(4) 0.0269(19) Uani 1 1 d . . . C11 C 0.1096(11) 0.9328(7) 0.6662(4) 0.0281(19) Uani 1 1 d . . . H11 H 0.0036 0.8854 0.6884 0.034 Uiso 1 1 calc R . . C12 C 0.0676(12) 0.9901(8) 0.6079(4) 0.036(2) Uani 1 1 d . . . H12 H -0.0676 0.9806 0.5901 0.043 Uiso 1 1 calc R . . C13 C 0.2206(13) 1.0601(8) 0.5761(4) 0.039(2) Uani 1 1 d . . . H13 H 0.1898 1.0988 0.5366 0.047 Uiso 1 1 calc R . . C14 C 0.4216(13) 1.0749(8) 0.6013(4) 0.041(2) Uani 1 1 d . . . H14 H 0.5271 1.1227 0.5791 0.049 Uiso 1 1 calc R . . C15 C 0.4631(11) 1.0187(8) 0.6589(4) 0.031(2) Uani 1 1 d . . . H15 H 0.5987 1.0298 0.6766 0.037 Uiso 1 1 calc R . . C16 C 0.5165(10) 0.8747(7) 0.8761(4) 0.0238(18) Uani 1 1 d . . . C17 C 0.6436(10) 0.9072(8) 0.9354(4) 0.0264(19) Uani 1 1 d . . . H17 H 0.7286 0.9935 0.9431 0.032 Uiso 1 1 calc R . . C18 C 0.6539(10) 0.8190(8) 0.9854(4) 0.0259(19) Uani 1 1 d . . . C19 C 0.8275(12) 0.7533(8) 1.1049(4) 0.0290(19) Uani 1 1 d . . . H19 H 0.6835 0.7171 1.1115 0.035 Uiso 1 1 calc R . . C20 C 0.9454(12) 0.6296(9) 1.0727(4) 0.040(2) Uani 1 1 d . . . H20A H 0.8661 0.5393 1.0756 0.048 Uiso 1 1 calc R . . H20B H 0.9749 0.6325 1.0233 0.048 Uiso 1 1 calc R . . C21 C 1.1393(12) 0.6523(9) 1.1170(4) 0.044(2) Uani 1 1 d . . . H21A H 1.1965 0.5642 1.1154 0.052 Uiso 1 1 calc R . . H21B H 1.2413 0.7202 1.1007 0.052 Uiso 1 1 calc R . . C22 C 1.0771(11) 0.7071(8) 1.1895(4) 0.036(2) Uani 1 1 d . . . H22A H 1.1960 0.7516 1.2198 0.043 Uiso 1 1 calc R . . H22B H 1.0043 0.6321 1.2108 0.043 Uiso 1 1 calc R . . C23 C 0.9353(11) 0.8151(8) 1.1778(4) 0.032(2) Uani 1 1 d . . . H23A H 1.0141 0.9067 1.1771 0.039 Uiso 1 1 calc R . . H23B H 0.8354 0.8254 1.2149 0.039 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cr1 0.0150(7) 0.0288(8) 0.0249(8) 0.0034(6) 0.0018(5) 0.0034(5) S1 0.0159(10) 0.0300(12) 0.0254(12) 0.0052(9) 0.0000(8) 0.0009(8) S2 0.0239(11) 0.0262(12) 0.0266(12) 0.0048(9) -0.0027(9) 0.0013(9) S3 0.0314(13) 0.0380(14) 0.0405(14) 0.0141(11) -0.0098(10) -0.0067(10) S4 0.0239(11) 0.0342(12) 0.0288(12) 0.0053(10) -0.0030(9) 0.0029(9) O1 0.050(4) 0.061(4) 0.047(4) 0.020(4) -0.002(3) 0.023(3) O2 0.038(4) 0.048(4) 0.047(4) 0.004(3) 0.006(3) -0.015(3) O3 0.049(4) 0.040(4) 0.037(4) 0.007(3) 0.014(3) 0.011(3) O4 0.053(4) 0.043(4) 0.040(4) 0.003(3) -0.014(3) 0.017(3) O5 0.018(3) 0.049(4) 0.057(4) 0.007(3) 0.005(3) -0.004(3) O6 0.015(3) 0.032(3) 0.032(3) 0.001(3) 0.011(2) 0.004(2) C1 0.033(5) 0.027(5) 0.024(5) 0.004(4) 0.002(4) -0.001(4) C2 0.039(5) 0.025(5) 0.023(5) -0.004(4) 0.004(4) -0.001(4) C3 0.039(5) 0.027(5) 0.027(5) 0.010(4) 0.000(4) -0.001(4) C4 0.027(5) 0.032(5) 0.027(5) 0.004(4) 0.005(4) 0.002(4) C5 0.014(4) 0.022(4) 0.038(5) 0.007(4) 0.007(4) 0.007(3) C6 0.013(4) 0.032(5) 0.032(5) 0.016(4) 0.003(3) 0.010(3) C7 0.013(4) 0.042(5) 0.038(5) -0.013(4) 0.007(4) 0.011(4) C8 0.016(4) 0.027(5) 0.023(5) 0.002(4) 0.002(3) 0.006(3) C9 0.018(4) 0.027(5) 0.026(5) 0.003(4) -0.001(3) 0.006(3) C10 0.026(5) 0.027(5) 0.029(5) 0.002(4) 0.005(4) 0.011(4) C11 0.017(4) 0.031(5) 0.039(5) 0.012(4) -0.003(4) 0.004(3) C12 0.028(5) 0.041(5) 0.040(6) 0.008(4) -0.014(4) 0.008(4) C13 0.057(6) 0.035(5) 0.024(5) 0.006(4) -0.012(4) 0.007(5) C14 0.042(6) 0.040(6) 0.040(6) 0.012(5) -0.002(4) -0.009(4) C15 0.014(4) 0.048(6) 0.033(5) 0.010(4) 0.002(4) 0.005(4) C16 0.015(4) 0.032(5) 0.025(5) 0.000(4) 0.008(3) 0.009(3) C17 0.020(4) 0.027(5) 0.029(5) -0.001(4) -0.002(4) -0.001(3) C18 0.019(4) 0.033(5) 0.024(5) 0.001(4) -0.001(3) 0.001(3) C19 0.032(5) 0.031(5) 0.023(5) 0.001(4) -0.005(4) 0.008(4) C20 0.044(6) 0.056(6) 0.022(5) 0.006(4) -0.002(4) 0.016(5) C21 0.036(5) 0.054(6) 0.047(6) 0.011(5) 0.007(5) 0.030(5) C22 0.021(4) 0.041(5) 0.049(6) 0.015(5) -0.009(4) 0.005(4) C23 0.024(5) 0.044(5) 0.028(5) -0.001(4) -0.006(4) 0.014(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cr1 C5 1.906(7) . ? Cr1 C3 1.914(9) . ? Cr1 C4 1.917(9) . ? Cr1 C2 1.926(8) . ? Cr1 C1 1.926(9) . ? Cr1 C6 1.993(7) . ? S1 C16 1.729(7) . ? S1 C8 1.774(7) . ? S2 C16 1.749(7) . ? S2 C9 1.750(7) . ? S3 C18 1.646(8) . ? S4 C18 1.776(7) . ? S4 C19 1.802(8) . ? O1 C1 1.140(8) . ? O2 C2 1.139(8) . ? O3 C3 1.147(9) . ? O4 C4 1.136(8) . ? O5 C5 1.147(8) . ? O6 C6 1.335(8) . ? O6 C7 1.472(8) . ? C6 C8 1.522(10) . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C8 C9 1.350(9) . ? C9 C10 1.487(10) . ? C10 C15 1.388(9) . ? C10 C11 1.420(9) . ? C11 C12 1.397(10) . ? C11 H11 0.9500 . ? C12 C13 1.375(10) . ? C12 H12 0.9500 . ? C13 C14 1.404(11) . ? C13 H13 0.9500 . ? C14 C15 1.378(10) . ? C14 H14 0.9500 . ? C15 H15 0.9500 . ? C16 C17 1.393(9) . ? C17 C18 1.423(10) . ? C17 H17 0.9500 . ? C19 C23 1.571(10) . ? C19 C20 1.578(10) . ? C19 H19 1.0000 . ? C20 C21 1.517(10) . ? C20 H20A 0.9900 . ? C20 H20B 0.9900 . ? C21 C22 1.504(10) . ? C21 H21A 0.9900 . ? C21 H21B 0.9900 . ? C22 C23 1.556(10) . ? C22 H22A 0.9900 . ? C22 H22B 0.9900 . ? C23 H23A 0.9900 . ? C23 H23B 0.9900 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C5 Cr1 C3 87.4(3) . . ? C5 Cr1 C4 91.6(3) . . ? C3 Cr1 C4 89.5(3) . . ? C5 Cr1 C2 178.7(3) . . ? C3 Cr1 C2 91.9(3) . . ? C4 Cr1 C2 87.3(3) . . ? C5 Cr1 C1 89.9(3) . . ? C3 Cr1 C1 90.5(3) . . ? C4 Cr1 C1 178.6(3) . . ? C2 Cr1 C1 91.2(3) . . ? C5 Cr1 C6 92.3(3) . . ? C3 Cr1 C6 178.4(3) . . ? C4 Cr1 C6 92.0(3) . . ? C2 Cr1 C6 88.5(3) . . ? C1 Cr1 C6 88.0(3) . . ? C16 S1 C8 94.5(4) . . ? C16 S2 C9 96.5(4) . . ? C18 S4 C19 103.1(4) . . ? C6 O6 C7 124.1(5) . . ? O1 C1 Cr1 179.5(7) . . ? O2 C2 Cr1 177.2(7) . . ? O3 C3 Cr1 178.3(7) . . ? O4 C4 Cr1 178.8(7) . . ? O5 C5 Cr1 175.7(6) . . ? O6 C6 C8 114.6(6) . . ? O6 C6 Cr1 121.0(5) . . ? C8 C6 Cr1 123.8(5) . . ? O6 C7 H7A 109.5 . . ? O6 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? O6 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C9 C8 C6 127.0(7) . . ? C9 C8 S1 118.6(6) . . ? C6 C8 S1 113.9(5) . . ? C8 C9 C10 127.6(7) . . ? C8 C9 S2 115.0(6) . . ? C10 C9 S2 117.3(5) . . ? C15 C10 C11 118.8(7) . . ? C15 C10 C9 121.5(7) . . ? C11 C10 C9 119.7(7) . . ? C12 C11 C10 119.2(7) . . ? C12 C11 H11 120.4 . . ? C10 C11 H11 120.4 . . ? C13 C12 C11 120.5(7) . . ? C13 C12 H12 119.8 . . ? C11 C12 H12 119.8 . . ? C12 C13 C14 120.8(8) . . ? C12 C13 H13 119.6 . . ? C14 C13 H13 119.6 . . ? C15 C14 C13 118.8(8) . . ? C15 C14 H14 120.6 . . ? C13 C14 H14 120.6 . . ? C14 C15 C10 121.9(7) . . ? C14 C15 H15 119.0 . . ? C10 C15 H15 119.0 . . ? C17 C16 S1 125.9(6) . . ? C17 C16 S2 118.7(6) . . ? S1 C16 S2 115.3(4) . . ? C16 C17 C18 124.0(7) . . ? C16 C17 H17 118.0 . . ? C18 C17 H17 118.0 . . ? C17 C18 S3 123.6(6) . . ? C17 C18 S4 112.7(5) . . ? S3 C18 S4 123.6(5) . . ? C23 C19 C20 105.3(6) . . ? C23 C19 S4 108.8(5) . . ? C20 C19 S4 113.6(5) . . ? C23 C19 H19 109.7 . . ? C20 C19 H19 109.7 . . ? S4 C19 H19 109.7 . . ? C21 C20 C19 104.3(6) . . ? C21 C20 H20A 110.9 . . ? C19 C20 H20A 110.9 . . ? C21 C20 H20B 110.9 . . ? C19 C20 H20B 110.9 . . ? H20A C20 H20B 108.9 . . ? C22 C21 C20 104.6(6) . . ? C22 C21 H21A 110.8 . . ? C20 C21 H21A 110.8 . . ? C22 C21 H21B 110.8 . . ? C20 C21 H21B 110.8 . . ? H21A C21 H21B 108.9 . . ? C21 C22 C23 103.2(6) . . ? C21 C22 H22A 111.1 . . ? C23 C22 H22A 111.1 . . ? C21 C22 H22B 111.1 . . ? C23 C22 H22B 111.1 . . ? H22A C22 H22B 109.1 . . ? C22 C23 C19 104.3(6) . . ? C22 C23 H23A 110.9 . . ? C19 C23 H23A 110.9 . . ? C22 C23 H23B 110.9 . . ? C19 C23 H23B 110.9 . . ? H23A C23 H23B 108.9 . . ? 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 C7 O6 C6 C8 8.9(9) . . . . ? C7 O6 C6 Cr1 -178.9(5) . . . . ? C5 Cr1 C6 O6 174.8(6) . . . . ? C4 Cr1 C6 O6 83.1(6) . . . . ? C2 Cr1 C6 O6 -4.2(6) . . . . ? C1 Cr1 C6 O6 -95.4(6) . . . . ? C5 Cr1 C6 C8 -13.7(6) . . . . ? C4 Cr1 C6 C8 -105.4(6) . . . . ? C2 Cr1 C6 C8 167.3(6) . . . . ? C1 Cr1 C6 C8 76.0(6) . . . . ? O6 C6 C8 C9 -117.1(8) . . . . ? Cr1 C6 C8 C9 70.9(9) . . . . ? O6 C6 C8 S1 71.1(7) . . . . ? Cr1 C6 C8 S1 -100.8(6) . . . . ? C16 S1 C8 C9 -1.3(6) . . . . ? C16 S1 C8 C6 171.2(5) . . . . ? C6 C8 C9 C10 11.0(12) . . . . ? S1 C8 C9 C10 -177.5(6) . . . . ? C6 C8 C9 S2 -171.2(6) . . . . ? S1 C8 C9 S2 0.3(8) . . . . ? C16 S2 C9 C8 0.9(6) . . . . ? C16 S2 C9 C10 178.9(5) . . . . ? C8 C9 C10 C15 -140.1(8) . . . . ? S2 C9 C10 C15 42.2(9) . . . . ? C8 C9 C10 C11 42.2(11) . . . . ? S2 C9 C10 C11 -135.5(6) . . . . ? C15 C10 C11 C12 1.2(11) . . . . ? C9 C10 C11 C12 179.0(7) . . . . ? C10 C11 C12 C13 -0.7(12) . . . . ? C11 C12 C13 C14 0.3(12) . . . . ? C12 C13 C14 C15 -0.4(12) . . . . ? C13 C14 C15 C10 1.0(12) . . . . ? C11 C10 C15 C14 -1.4(11) . . . . ? C9 C10 C15 C14 -179.1(7) . . . . ? C8 S1 C16 C17 -174.5(7) . . . . ? C8 S1 C16 S2 1.9(4) . . . . ? C9 S2 C16 C17 174.8(6) . . . . ? C9 S2 C16 S1 -1.8(4) . . . . ? S1 C16 C17 C18 -1.8(11) . . . . ? S2 C16 C17 C18 -178.0(6) . . . . ? C16 C17 C18 S3 1.4(11) . . . . ? C16 C17 C18 S4 178.2(6) . . . . ? C19 S4 C18 C17 -176.7(5) . . . . ? C19 S4 C18 S3 0.1(6) . . . . ? C18 S4 C19 C23 -164.4(5) . . . . ? C18 S4 C19 C20 78.6(6) . . . . ? C23 C19 C20 C21 -15.0(8) . . . . ? S4 C19 C20 C21 104.0(6) . . . . ? C19 C20 C21 C22 36.5(8) . . . . ? C20 C21 C22 C23 -43.8(8) . . . . ? C21 C22 C23 C19 33.2(8) . . . . ? C20 C19 C23 C22 -11.0(8) . . . . ? S4 C19 C23 C22 -133.1(5) . . . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.471 _refine_diff_density_min -0.472 _refine_diff_density_rms 0.117 # Attachment 'Prod4aChemCom.cif' data_3 _database_code_depnum_ccdc_archive 'CCDC 664204' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C16 H16 S4' _chemical_formula_sum 'C16 H16 S4' _chemical_formula_weight 336.53 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)/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 15.354(6) _cell_length_b 11.400(3) _cell_length_c 8.9237(17) _cell_angle_alpha 90.00 _cell_angle_beta 98.52(2) _cell_angle_gamma 90.00 _cell_volume 1544.8(8) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 3086 _cell_measurement_theta_min 2.23 _cell_measurement_theta_max 24.64 _exptl_crystal_description plate _exptl_crystal_colour orange _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.447 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 704 _exptl_absorpt_coefficient_mu 0.601 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.842 _exptl_absorpt_correction_T_max 0.990 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2001)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 'CCD area detector' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 14425 _diffrn_reflns_av_R_equivalents 0.0518 _diffrn_reflns_av_sigmaI/netI 0.0406 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.23 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2717 _reflns_number_gt 2280 _reflns_threshold_expression >2sigma(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^)+(0.0398P)^2^+0.2986P] 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 2717 _refine_ls_number_parameters 181 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0466 _refine_ls_R_factor_gt 0.0372 _refine_ls_wR_factor_ref 0.0896 _refine_ls_wR_factor_gt 0.0862 _refine_ls_goodness_of_fit_ref 1.096 _refine_ls_restrained_S_all 1.096 _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 0.93683(4) 0.02989(5) 0.33411(7) 0.02810(18) Uani 1 1 d . . . S2 S 0.95725(4) 0.21083(5) 0.11241(7) 0.02831(18) Uani 1 1 d . . . S3 S 0.76749(4) 0.04786(5) 0.45706(7) 0.03121(18) Uani 1 1 d . . . S4 S 0.64638(4) 0.22850(5) 0.28983(8) 0.03341(19) Uani 1 1 d . . . C1 C 1.03154(16) 0.0276(2) 0.2487(3) 0.0291(6) Uani 1 1 d . . . H1 H 1.0747 -0.0315 0.2747 0.035 Uiso 1 1 calc R . . C2 C 1.04331(15) 0.10923(19) 0.1466(3) 0.0243(5) Uani 1 1 d . . . C3 C 1.11886(15) 0.1214(2) 0.0640(2) 0.0247(5) Uani 1 1 d . . . C4 C 1.17771(15) 0.0283(2) 0.0593(3) 0.0272(6) Uani 1 1 d . . . H4 H 1.1688 -0.0429 0.1102 0.033 Uiso 1 1 calc R . . C5 C 1.24835(16) 0.0386(2) -0.0184(3) 0.0316(6) Uani 1 1 d . . . H5 H 1.2879 -0.0253 -0.0205 0.038 Uiso 1 1 calc R . . C6 C 1.26191(16) 0.1418(2) -0.0935(3) 0.0322(6) Uani 1 1 d . . . H6 H 1.3102 0.1483 -0.1483 0.039 Uiso 1 1 calc R . . C7 C 1.20538(16) 0.2347(2) -0.0887(3) 0.0332(6) Uani 1 1 d . . . H7 H 1.2152 0.3060 -0.1387 0.040 Uiso 1 1 calc R . . C8 C 1.13406(16) 0.2245(2) -0.0110(3) 0.0310(6) Uani 1 1 d . . . H8 H 1.0950 0.2889 -0.0089 0.037 Uiso 1 1 calc R . . C9 C 0.89200(15) 0.15239(19) 0.2367(3) 0.0243(5) Uani 1 1 d . . . C10 C 0.81079(15) 0.2001(2) 0.2448(3) 0.0267(5) Uani 1 1 d . . . H10 H 0.7951 0.2687 0.1865 0.032 Uiso 1 1 calc R . . C11 C 0.74842(15) 0.15625(19) 0.3321(3) 0.0247(5) Uani 1 1 d . . . C12 C 0.57108(15) 0.1412(2) 0.3820(3) 0.0274(6) Uani 1 1 d . . . H12 H 0.5960 0.1274 0.4906 0.033 Uiso 1 1 calc R . . C13 C 0.54825(16) 0.0240(2) 0.3007(3) 0.0317(6) Uani 1 1 d . . . H13A H 0.5965 -0.0017 0.2460 0.038 Uiso 1 1 calc R . . H13B H 0.5376 -0.0378 0.3739 0.038 Uiso 1 1 calc R . . C14 C 0.46559(17) 0.0486(2) 0.1911(3) 0.0347(6) Uani 1 1 d . . . H14A H 0.4324 -0.0245 0.1627 0.042 Uiso 1 1 calc R . . H14B H 0.4795 0.0872 0.0981 0.042 Uiso 1 1 calc R . . C15 C 0.41372(17) 0.1304(2) 0.2803(3) 0.0389(7) Uani 1 1 d . . . H15A H 0.3713 0.1779 0.2110 0.047 Uiso 1 1 calc R . . H15B H 0.3811 0.0853 0.3488 0.047 Uiso 1 1 calc R . . C16 C 0.48311(16) 0.2084(2) 0.3705(3) 0.0330(6) Uani 1 1 d . . . H16A H 0.4680 0.2238 0.4727 0.040 Uiso 1 1 calc R . . H16B H 0.4872 0.2843 0.3181 0.040 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.0286(4) 0.0283(3) 0.0263(3) 0.0080(3) 0.0004(3) 0.0026(3) S2 0.0290(3) 0.0238(3) 0.0322(4) 0.0069(3) 0.0047(3) 0.0028(3) S3 0.0326(4) 0.0316(4) 0.0288(4) 0.0064(3) 0.0026(3) 0.0024(3) S4 0.0297(4) 0.0260(4) 0.0451(4) 0.0080(3) 0.0075(3) 0.0043(3) C1 0.0283(13) 0.0267(13) 0.0309(14) 0.0034(11) -0.0004(11) 0.0051(11) C2 0.0264(13) 0.0215(12) 0.0234(12) -0.0019(10) -0.0019(10) -0.0004(10) C3 0.0248(12) 0.0253(13) 0.0222(12) -0.0035(10) -0.0027(10) -0.0015(10) C4 0.0294(14) 0.0209(12) 0.0292(14) -0.0014(10) -0.0028(11) -0.0035(10) C5 0.0253(14) 0.0275(14) 0.0395(16) -0.0095(12) -0.0033(11) 0.0007(11) C6 0.0273(14) 0.0372(15) 0.0324(14) -0.0071(12) 0.0053(11) -0.0051(11) C7 0.0318(14) 0.0336(14) 0.0344(15) 0.0048(12) 0.0055(12) -0.0024(12) C8 0.0329(14) 0.0255(13) 0.0348(15) 0.0036(11) 0.0054(12) 0.0068(11) C9 0.0277(13) 0.0217(12) 0.0220(13) -0.0013(10) -0.0017(10) -0.0021(10) C10 0.0309(14) 0.0211(12) 0.0270(13) 0.0043(10) 0.0005(11) -0.0003(10) C11 0.0298(13) 0.0206(12) 0.0224(13) -0.0031(10) -0.0005(10) -0.0005(10) C12 0.0298(14) 0.0248(13) 0.0280(14) -0.0011(11) 0.0057(11) 0.0006(10) C13 0.0333(15) 0.0227(13) 0.0392(15) -0.0005(11) 0.0061(12) 0.0031(11) C14 0.0436(16) 0.0269(14) 0.0322(15) -0.0046(11) 0.0009(12) 0.0047(12) C15 0.0317(15) 0.0396(16) 0.0435(16) -0.0070(13) -0.0004(12) 0.0070(12) C16 0.0321(14) 0.0263(13) 0.0421(16) -0.0035(12) 0.0098(12) 0.0032(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 C9 1.733(2) . ? S1 C1 1.739(3) . ? S2 C9 1.734(2) . ? S2 C2 1.750(2) . ? S3 C11 1.661(2) . ? S4 C11 1.761(2) . ? S4 C12 1.813(2) . ? C1 C2 1.333(3) . ? C1 H1 0.9500 . ? C2 C3 1.470(3) . ? C3 C8 1.389(3) . ? C3 C4 1.399(3) . ? C4 C5 1.376(3) . ? C4 H4 0.9500 . ? C5 C6 1.385(3) . ? C5 H5 0.9500 . ? C6 C7 1.374(3) . ? C6 H6 0.9500 . ? C7 C8 1.385(3) . ? C7 H7 0.9500 . ? C8 H8 0.9500 . ? C9 C10 1.372(3) . ? C10 C11 1.413(3) . ? C10 H10 0.9500 . ? C12 C13 1.537(3) . ? C12 C16 1.543(3) . ? C12 H12 1.0000 . ? C13 C14 1.509(3) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 C15 1.525(3) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C15 C16 1.523(3) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C9 S1 C1 95.05(11) . . ? C9 S2 C2 97.31(11) . . ? C11 S4 C12 104.66(11) . . ? C2 C1 S1 119.73(19) . . ? C2 C1 H1 120.1 . . ? S1 C1 H1 120.1 . . ? C1 C2 C3 127.3(2) . . ? C1 C2 S2 113.94(18) . . ? C3 C2 S2 118.79(17) . . ? C8 C3 C4 118.2(2) . . ? C8 C3 C2 121.5(2) . . ? C4 C3 C2 120.3(2) . . ? C5 C4 C3 120.8(2) . . ? C5 C4 H4 119.6 . . ? C3 C4 H4 119.6 . . ? C4 C5 C6 120.2(2) . . ? C4 C5 H5 119.9 . . ? C6 C5 H5 119.9 . . ? C7 C6 C5 119.9(2) . . ? C7 C6 H6 120.0 . . ? C5 C6 H6 120.0 . . ? C6 C7 C8 120.1(2) . . ? C6 C7 H7 120.0 . . ? C8 C7 H7 120.0 . . ? C7 C8 C3 120.9(2) . . ? C7 C8 H8 119.5 . . ? C3 C8 H8 119.5 . . ? C10 C9 S1 126.15(18) . . ? C10 C9 S2 119.79(18) . . ? S1 C9 S2 113.98(13) . . ? C9 C10 C11 125.7(2) . . ? C9 C10 H10 117.1 . . ? C11 C10 H10 117.1 . . ? C10 C11 S3 124.56(18) . . ? C10 C11 S4 111.74(17) . . ? S3 C11 S4 123.69(14) . . ? C13 C12 C16 105.31(19) . . ? C13 C12 S4 112.30(16) . . ? C16 C12 S4 107.95(16) . . ? C13 C12 H12 110.4 . . ? C16 C12 H12 110.4 . . ? S4 C12 H12 110.4 . . ? C14 C13 C12 104.79(19) . . ? C14 C13 H13A 110.8 . . ? C12 C13 H13A 110.8 . . ? C14 C13 H13B 110.8 . . ? C12 C13 H13B 110.8 . . ? H13A C13 H13B 108.9 . . ? C13 C14 C15 103.3(2) . . ? C13 C14 H14A 111.1 . . ? C15 C14 H14A 111.1 . . ? C13 C14 H14B 111.1 . . ? C15 C14 H14B 111.1 . . ? H14A C14 H14B 109.1 . . ? C16 C15 C14 104.7(2) . . ? C16 C15 H15A 110.8 . . ? C14 C15 H15A 110.8 . . ? C16 C15 H15B 110.8 . . ? C14 C15 H15B 110.8 . . ? H15A C15 H15B 108.9 . . ? C15 C16 C12 106.43(19) . . ? C15 C16 H16A 110.4 . . ? C12 C16 H16A 110.4 . . ? C15 C16 H16B 110.4 . . ? C12 C16 H16B 110.4 . . ? H16A C16 H16B 108.6 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C9 S1 C1 C2 0.4(2) . . . . ? S1 C1 C2 C3 179.65(18) . . . . ? S1 C1 C2 S2 -0.1(3) . . . . ? C9 S2 C2 C1 -0.3(2) . . . . ? C9 S2 C2 C3 179.96(17) . . . . ? C1 C2 C3 C8 -164.1(2) . . . . ? S2 C2 C3 C8 15.6(3) . . . . ? C1 C2 C3 C4 15.9(4) . . . . ? S2 C2 C3 C4 -164.37(17) . . . . ? C8 C3 C4 C5 -0.4(3) . . . . ? C2 C3 C4 C5 179.6(2) . . . . ? C3 C4 C5 C6 -0.2(4) . . . . ? C4 C5 C6 C7 0.9(4) . . . . ? C5 C6 C7 C8 -1.1(4) . . . . ? C6 C7 C8 C3 0.6(4) . . . . ? C4 C3 C8 C7 0.2(4) . . . . ? C2 C3 C8 C7 -179.8(2) . . . . ? C1 S1 C9 C10 176.0(2) . . . . ? C1 S1 C9 S2 -0.57(15) . . . . ? C2 S2 C9 C10 -176.24(19) . . . . ? C2 S2 C9 S1 0.53(15) . . . . ? S1 C9 C10 C11 -1.3(4) . . . . ? S2 C9 C10 C11 175.04(18) . . . . ? C9 C10 C11 S3 7.8(4) . . . . ? C9 C10 C11 S4 -170.9(2) . . . . ? C12 S4 C11 C10 168.66(16) . . . . ? C12 S4 C11 S3 -10.10(18) . . . . ? C11 S4 C12 C13 -72.56(19) . . . . ? C11 S4 C12 C16 171.79(16) . . . . ? C16 C12 C13 C14 24.8(2) . . . . ? S4 C12 C13 C14 -92.5(2) . . . . ? C12 C13 C14 C15 -38.4(3) . . . . ? C13 C14 C15 C16 37.4(3) . . . . ? C14 C15 C16 C12 -21.9(3) . . . . ? C13 C12 C16 C15 -1.6(3) . . . . ? S4 C12 C16 C15 118.60(19) . . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.281 _refine_diff_density_min -0.221 _refine_diff_density_rms 0.061 # Attachment 'Prod4dChemCom.cif' data_4 _database_code_depnum_ccdc_archive 'CCDC 664205' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C12 H10 S3' _chemical_formula_sum 'C12 H10 S3' _chemical_formula_weight 250.38 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 Orthorhombic _symmetry_space_group_name_H-M Pbca _symmetry_space_group_name_Hall '-P 2ac 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 14.836(2) _cell_length_b 5.6318(9) _cell_length_c 26.458(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2210.7(6) _cell_formula_units_Z 8 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 1169 _cell_measurement_theta_min 2.75 _cell_measurement_theta_max 20.95 _exptl_crystal_description plate _exptl_crystal_colour orange _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.505 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1040 _exptl_absorpt_coefficient_mu 0.630 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.853 _exptl_absorpt_correction_T_max 0.957 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2001)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 'CCD area detector' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 19688 _diffrn_reflns_av_R_equivalents 0.0965 _diffrn_reflns_av_sigmaI/netI 0.0470 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -31 _diffrn_reflns_limit_l_max 31 _diffrn_reflns_theta_min 1.54 _diffrn_reflns_theta_max 25.00 _reflns_number_total 1946 _reflns_number_gt 1474 _reflns_threshold_expression >2sigma(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^)+(0.0728P)^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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1946 _refine_ls_number_parameters 137 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0603 _refine_ls_R_factor_gt 0.0394 _refine_ls_wR_factor_ref 0.1282 _refine_ls_wR_factor_gt 0.1086 _refine_ls_goodness_of_fit_ref 1.071 _refine_ls_restrained_S_all 1.071 _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 0.92295(6) 0.18017(15) 0.62835(3) 0.0298(3) Uani 1 1 d . . . S2 S 0.92017(5) 0.13778(15) 0.73908(3) 0.0243(3) Uani 1 1 d . . . S3 S 0.83189(6) 0.53807(15) 0.78726(3) 0.0238(3) Uani 1 1 d . . . C1 C 0.8336(2) 0.5751(6) 0.59354(12) 0.0296(8) Uani 1 1 d . . . H1A H 0.7685 0.6030 0.5956 0.044 Uiso 1 1 calc R . . H1B H 0.8476 0.4910 0.5621 0.044 Uiso 1 1 calc R . . H1C H 0.8654 0.7275 0.5941 0.044 Uiso 1 1 calc R . . C2 C 0.8631(2) 0.4273(6) 0.63784(12) 0.0246(8) Uani 1 1 d . . . C3 C 0.8395(2) 0.5083(6) 0.68590(11) 0.0232(8) Uani 1 1 d . . . H3 H 0.8048 0.6499 0.6876 0.028 Uiso 1 1 calc R . . C4 C 0.8621(2) 0.4008(5) 0.73139(12) 0.0205(7) Uani 1 1 d . . . C5 C 0.9207(2) 0.1491(6) 0.80463(12) 0.0239(8) Uani 1 1 d . . . H5 H 0.9486 0.0260 0.8235 0.029 Uiso 1 1 calc R . . C6 C 0.8817(2) 0.3311(5) 0.82842(12) 0.0213(7) Uani 1 1 d . . . C7 C 0.8781(2) 0.3783(6) 0.88292(11) 0.0223(7) Uani 1 1 d . . . C8 C 0.8377(2) 0.5837(6) 0.90180(13) 0.0282(8) Uani 1 1 d . . . H8 H 0.8107 0.6938 0.8792 0.034 Uiso 1 1 calc R . . C9 C 0.8366(2) 0.6282(7) 0.95359(13) 0.0334(9) Uani 1 1 d . . . H9 H 0.8082 0.7674 0.9662 0.040 Uiso 1 1 calc R . . C10 C 0.8764(2) 0.4713(6) 0.98647(13) 0.0346(9) Uani 1 1 d . . . H10 H 0.8765 0.5031 1.0217 0.041 Uiso 1 1 calc R . . C11 C 0.9162(2) 0.2669(7) 0.96814(13) 0.0330(9) Uani 1 1 d . . . H11 H 0.9432 0.1577 0.9909 0.040 Uiso 1 1 calc R . . C12 C 0.9171(2) 0.2204(6) 0.91691(13) 0.0277(8) Uani 1 1 d . . . H12 H 0.9446 0.0791 0.9048 0.033 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.0318(5) 0.0269(5) 0.0306(5) -0.0051(4) -0.0032(4) 0.0066(4) S2 0.0263(5) 0.0191(5) 0.0276(5) -0.0019(3) -0.0014(3) 0.0056(4) S3 0.0255(5) 0.0190(5) 0.0271(5) -0.0008(4) 0.0015(3) 0.0045(3) C1 0.032(2) 0.026(2) 0.0316(19) 0.0037(15) 0.0024(15) 0.0000(15) C2 0.0204(18) 0.0227(18) 0.0308(19) -0.0007(14) -0.0018(14) -0.0038(15) C3 0.0197(17) 0.0192(18) 0.0308(19) -0.0008(14) -0.0010(14) -0.0003(14) C4 0.0150(16) 0.0164(17) 0.0302(18) -0.0037(14) 0.0015(14) 0.0005(13) C5 0.0255(18) 0.0204(18) 0.0259(18) 0.0013(14) -0.0036(14) 0.0025(14) C6 0.0150(16) 0.0197(18) 0.0291(17) 0.0042(14) -0.0019(13) -0.0010(14) C7 0.0156(16) 0.0250(18) 0.0263(18) 0.0017(14) 0.0023(14) -0.0040(14) C8 0.0265(19) 0.0246(19) 0.0335(19) 0.0006(15) 0.0005(15) 0.0015(15) C9 0.036(2) 0.030(2) 0.035(2) -0.0059(16) 0.0076(16) 0.0014(16) C10 0.036(2) 0.037(2) 0.0301(19) -0.0022(17) 0.0054(17) -0.0014(18) C11 0.035(2) 0.034(2) 0.030(2) 0.0046(17) -0.0014(15) 0.0031(17) C12 0.0260(19) 0.0203(18) 0.037(2) -0.0018(16) 0.0031(15) 0.0026(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 C2 1.670(3) . ? S2 C4 1.726(3) . ? S2 C5 1.736(3) . ? S3 C4 1.727(3) . ? S3 C6 1.758(3) . ? C1 C2 1.503(4) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C2 C3 1.396(4) . ? C3 C4 1.389(4) . ? C3 H3 0.9500 . ? C5 C6 1.335(4) . ? C5 H5 0.9500 . ? C6 C7 1.467(4) . ? C7 C12 1.391(4) . ? C7 C8 1.395(4) . ? C8 C9 1.393(5) . ? C8 H8 0.9500 . ? C9 C10 1.374(5) . ? C9 H9 0.9500 . ? C10 C11 1.382(5) . ? C10 H10 0.9500 . ? C11 C12 1.380(5) . ? C11 H11 0.9500 . ? C12 H12 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 C4 S2 C5 95.06(15) . . ? C4 S3 C6 97.14(15) . . ? C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? C3 C2 C1 117.1(3) . . ? C3 C2 S1 122.9(3) . . ? C1 C2 S1 120.0(2) . . ? C4 C3 C2 125.9(3) . . ? C4 C3 H3 117.1 . . ? C2 C3 H3 117.1 . . ? C3 C4 S2 126.7(2) . . ? C3 C4 S3 118.9(2) . . ? S2 C4 S3 114.39(18) . . ? C6 C5 S2 119.9(3) . . ? C6 C5 H5 120.1 . . ? S2 C5 H5 120.1 . . ? C5 C6 C7 128.2(3) . . ? C5 C6 S3 113.5(2) . . ? C7 C6 S3 118.2(2) . . ? C12 C7 C8 118.5(3) . . ? C12 C7 C6 120.3(3) . . ? C8 C7 C6 121.2(3) . . ? C9 C8 C7 120.4(3) . . ? C9 C8 H8 119.8 . . ? C7 C8 H8 119.8 . . ? C10 C9 C8 120.1(3) . . ? C10 C9 H9 119.9 . . ? C8 C9 H9 119.9 . . ? C9 C10 C11 119.8(3) . . ? C9 C10 H10 120.1 . . ? C11 C10 H10 120.1 . . ? C12 C11 C10 120.5(3) . . ? C12 C11 H11 119.8 . . ? C10 C11 H11 119.8 . . ? C11 C12 C7 120.6(3) . . ? C11 C12 H12 119.7 . . ? C7 C12 H12 119.7 . . ? 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 C1 C2 C3 C4 -178.4(3) . . . . ? S1 C2 C3 C4 0.6(5) . . . . ? C2 C3 C4 S2 -2.8(5) . . . . ? C2 C3 C4 S3 176.3(3) . . . . ? C5 S2 C4 C3 178.0(3) . . . . ? C5 S2 C4 S3 -1.2(2) . . . . ? C6 S3 C4 C3 -177.6(2) . . . . ? C6 S3 C4 S2 1.7(2) . . . . ? C4 S2 C5 C6 0.1(3) . . . . ? S2 C5 C6 C7 -177.2(2) . . . . ? S2 C5 C6 S3 1.1(3) . . . . ? C4 S3 C6 C5 -1.6(3) . . . . ? C4 S3 C6 C7 176.9(2) . . . . ? C5 C6 C7 C12 -1.3(5) . . . . ? S3 C6 C7 C12 -179.6(2) . . . . ? C5 C6 C7 C8 177.2(3) . . . . ? S3 C6 C7 C8 -1.1(4) . . . . ? C12 C7 C8 C9 0.0(5) . . . . ? C6 C7 C8 C9 -178.6(3) . . . . ? C7 C8 C9 C10 0.8(5) . . . . ? C8 C9 C10 C11 -1.1(5) . . . . ? C9 C10 C11 C12 0.6(5) . . . . ? C10 C11 C12 C7 0.1(5) . . . . ? C8 C7 C12 C11 -0.4(5) . . . . ? C6 C7 C12 C11 178.2(3) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.364 _refine_diff_density_min -0.411 _refine_diff_density_rms 0.132