# Supplementary Material (ESI) for Perkin Transactions # This journal is © The Royal Society of Chemistry 2001 data_GLOBAL _journal_coden_Cambridge 188 # 1. SUBMISSION DETAILS _publ_contact_author_name 'Gleiter, Rolf' _publ_contact_author_address ; Organisch-Chemisches Institut Universit\"at Heidelberg Im Neuenheimer Feld 270 D-69120 Heidelberg Germany ; _publ_contact_author_phone '049 6221 54- 8400' _publ_contact_author_fax '049 6221 54- 4205' _publ_contact_author_email 'rolf.gleiter@urz.uni-heidelberg.de' _publ_requested_journal 'Perkin Transactions 1 ' _publ_requested_coeditor_name ? _publ_contact_letter ; paper submitted for publication in Perkin Transactions 1 ; #====================================================================== # 3. TITLE AND AUTHOR LIST _publ_section_title ; Cyclic Thiatetraynes - Syntheses and Structural Properties ; loop_ _publ_author_name _publ_author_address 'Rausch, Bernhard J.' ; Organisch-Chemisches Institut Universit\"at Heidelberg Im Neuenheimer Feld 270 69120 Heidelberg Bundesrepublik Deutschland ; 'Werz, Daniel B.' ; Organisch-Chemisches Institut Universit\"at Heidelberg Im Neuenheimer Feld 270 69120 Heidelberg Bundesrepublik Deutschland ; 'Rittinger, Stefan' ; Organisch-Chemisches Institut Universit\"at Heidelberg Im Neuenheimer Feld 270 69120 Heidelberg Bundesrepublik Deutschland ; 'Gleiter, Rolf' ; Organisch-Chemisches Institut Universit\"at Heidelberg Im Neuenheimer Feld 270 69120 Heidelberg Bundesrepublik Deutschland ; 'Oeser, Thomas' ; Organisch-Chemisches Institut Universit\"at Heidelberg Im Neuenheimer Feld 270 69120 Heidelberg Bundesrepublik Deutschland ; 'Rominger, Frank' ; Organisch-Chemisches Institut Universit\"at Heidelberg Im Neuenheimer Feld 270 69120 Heidelberg Bundesrepublik Deutschland ; #================================================================ data_br42_4inpaper _database_code_CSD 172996 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H32 S2 Si4' _chemical_formula_weight 448.94 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Si' 'Si' 0.0817 0.0704 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'S' 'S' 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 7.34830(10) _cell_length_b 12.1868(2) _cell_length_c 15.0313(2) _cell_angle_alpha 90.00 _cell_angle_beta 98.2280(10) _cell_angle_gamma 90.00 _cell_volume 1332.23(3) _cell_formula_units_Z 2 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description polyhedron _exptl_crystal_colour colorless _exptl_crystal_size_max .21 _exptl_crystal_size_mid .20 _exptl_crystal_size_min .18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.119 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 480 _exptl_absorpt_coefficient_mu 0.383 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.74 _exptl_absorpt_correction_T_max 0.95 _exptl_absorpt_process_details 'Blessing, Acta Cryst. (1995) A51 33-38.' _exptl_special_details ; ? ; _diffrn_ambient_temperature 200(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 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13420 _diffrn_reflns_av_R_equivalents 0.0341 _diffrn_reflns_av_sigmaI/netI 0.0248 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.16 _diffrn_reflns_theta_max 27.41 _reflns_number_total 3032 _reflns_number_gt 2441 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _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^)+(0.0457P)^2^+0.5664P] 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 noref _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3032 _refine_ls_number_parameters 122 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0482 _refine_ls_R_factor_gt 0.0359 _refine_ls_wR_factor_ref 0.0968 _refine_ls_wR_factor_gt 0.0912 _refine_ls_goodness_of_fit_ref 1.068 _refine_ls_restrained_S_all 1.068 _refine_ls_shift/su_max 0.075 _refine_ls_shift/su_mean 0.003 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 Si1 Si 0.06978(7) 0.96992(4) 0.75034(3) 0.03040(14) Uani 1 1 d . . . Si2 Si -0.24664(7) 0.98715(4) 0.75376(3) 0.02728(13) Uani 1 1 d . . . S1 S -0.34824(8) 1.29941(4) 0.48767(3) 0.04158(16) Uani 1 1 d . . . C3 C -0.3387(2) 1.06515(16) 0.65179(12) 0.0319(4) Uani 1 1 d . . . C4 C -0.3951(3) 1.11189(15) 0.58316(12) 0.0324(4) Uani 1 1 d . . . C5 C -0.4614(3) 1.16924(17) 0.49877(13) 0.0383(4) Uani 1 1 d . . . H5A H -0.5953 1.1820 0.4954 0.046 Uiso 1 1 calc R . . H5B H -0.4420 1.1215 0.4477 0.046 Uiso 1 1 calc R . . C7 C -0.1141(3) 1.25121(19) 0.48670(14) 0.0448(5) Uani 1 1 d . . . H7A H -0.0318 1.3154 0.4856 0.054 Uiso 1 1 calc R . . H7B H -0.0737 1.2100 0.5428 0.054 Uiso 1 1 calc R . . C8 C -0.0958(3) 1.18047(17) 0.40946(13) 0.0387(5) Uani 1 1 d . . . C9 C -0.0889(3) 1.12186(17) 0.34547(13) 0.0371(4) Uani 1 1 d . . . C11 C 0.1787(3) 1.10311(17) 0.72846(15) 0.0420(5) Uani 1 1 d . . . H11A H 0.3060 1.0904 0.7185 0.063 Uiso 1 1 calc R . . H11B H 0.1776 1.1517 0.7804 0.063 Uiso 1 1 calc R . . H11C H 0.1100 1.1374 0.6750 0.063 Uiso 1 1 calc R . . C12 C 0.1865(3) 0.9035(2) 0.85571(14) 0.0452(5) Uani 1 1 d . . . H12A H 0.1329 0.8308 0.8622 0.068 Uiso 1 1 calc R . . H12B H 0.1696 0.9490 0.9076 0.068 Uiso 1 1 calc R . . H12C H 0.3181 0.8959 0.8524 0.068 Uiso 1 1 calc R . . C21 C -0.3565(3) 0.84838(16) 0.74561(13) 0.0391(4) Uani 1 1 d . . . H21A H -0.4905 0.8565 0.7384 0.059 Uiso 1 1 calc R . . H21B H -0.3148 0.8067 0.8005 0.059 Uiso 1 1 calc R . . H21C H -0.3218 0.8092 0.6936 0.059 Uiso 1 1 calc R . . C22 C -0.3009(3) 1.06180(17) 0.85559(13) 0.0378(4) Uani 1 1 d . . . H22A H -0.2420 1.1341 0.8588 0.057 Uiso 1 1 calc R . . H22B H -0.2547 1.0196 0.9096 0.057 Uiso 1 1 calc R . . H22C H -0.4343 1.0708 0.8517 0.057 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 Si1 0.0272(3) 0.0357(3) 0.0291(3) 0.0011(2) 0.00669(19) 0.0038(2) Si2 0.0261(2) 0.0295(3) 0.0268(2) 0.00031(19) 0.00567(18) 0.00015(19) S1 0.0639(4) 0.0305(3) 0.0329(3) 0.0009(2) 0.0159(2) 0.0059(2) C3 0.0293(9) 0.0345(10) 0.0326(9) 0.0001(8) 0.0063(7) -0.0030(8) C4 0.0334(10) 0.0333(10) 0.0310(10) -0.0018(8) 0.0061(7) -0.0031(8) C5 0.0443(11) 0.0406(11) 0.0291(9) 0.0028(8) 0.0017(8) -0.0019(9) C7 0.0511(12) 0.0518(13) 0.0323(10) -0.0059(9) 0.0091(9) -0.0111(10) C8 0.0377(11) 0.0437(12) 0.0358(10) 0.0023(9) 0.0092(8) -0.0031(9) C9 0.0354(10) 0.0423(11) 0.0349(10) 0.0005(9) 0.0095(8) 0.0029(8) C11 0.0341(10) 0.0409(11) 0.0513(12) 0.0023(10) 0.0074(9) -0.0023(9) C12 0.0420(11) 0.0583(14) 0.0355(11) 0.0092(10) 0.0060(9) 0.0113(10) C21 0.0457(11) 0.0336(10) 0.0375(10) 0.0021(8) 0.0040(9) -0.0057(9) C22 0.0407(11) 0.0414(11) 0.0322(10) -0.0038(8) 0.0087(8) 0.0014(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Si1 C9 1.845(2) 3_576 ? Si1 C11 1.860(2) . ? Si1 C12 1.874(2) . ? Si1 Si2 2.3425(7) . ? Si2 C3 1.847(2) . ? Si2 C21 1.870(2) . ? Si2 C22 1.8719(19) . ? S1 C5 1.810(2) . ? S1 C7 1.820(2) . ? C3 C4 1.199(3) . ? C4 C5 1.469(3) . ? C7 C8 1.468(3) . ? C8 C9 1.205(3) . ? C9 Si1 1.845(2) 3_576 ? 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 Si1 C11 107.96(10) 3_576 . ? C9 Si1 C12 108.72(10) 3_576 . ? C11 Si1 C12 111.72(11) . . ? C9 Si1 Si2 104.96(7) 3_576 . ? C11 Si1 Si2 112.29(7) . . ? C12 Si1 Si2 110.86(7) . . ? C3 Si2 C21 107.91(9) . . ? C3 Si2 C22 109.44(9) . . ? C21 Si2 C22 110.65(9) . . ? C3 Si2 Si1 105.94(6) . . ? C21 Si2 Si1 109.75(7) . . ? C22 Si2 Si1 112.93(7) . . ? C5 S1 C7 99.51(10) . . ? C4 C3 Si2 176.81(17) . . ? C3 C4 C5 179.1(2) . . ? C4 C5 S1 113.37(14) . . ? C8 C7 S1 112.94(15) . . ? C9 C8 C7 177.2(2) . . ? C8 C9 Si1 177.82(19) . 3_576 ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.41 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.637 _refine_diff_density_min -0.448 _refine_diff_density_rms 0.055 #===END data_339RITTM_5inpaper _database_code_CSD 172997 _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1,10-Dithiacyclooctadeca-3,7,12,16-tetrayne (5) ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H16 S2' _chemical_formula_weight 272.4 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 'P b c a' 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 9.846(2) _cell_length_b 9.030(2) _cell_length_c 16.153(3) _cell_angle_alpha 90.0 _cell_angle_beta 90.0 _cell_angle_gamma 90.0 _cell_volume 1436.2(5) _cell_formula_units_Z 4 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 9 _cell_measurement_theta_max 20 _exptl_crystal_description colourless _exptl_crystal_colour polyhedron _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.50 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.26 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 576 _exptl_absorpt_coefficient_mu 0.35 _exptl_absorpt_correction_type semi-empirical _exptl_absorpt_correction_T_min 0.921 _exptl_absorpt_correction_T_max 1.0 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(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 NONIUS_CAD4 _diffrn_measurement_method '\w-2\q-scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 60 _diffrn_standards_interval_time 100 _diffrn_standards_decay_% 3.3 _diffrn_reflns_number 1992 _diffrn_reflns_av_R_equivalents 0.000 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.52 _diffrn_reflns_theta_max 27.90 _reflns_number_total 1712 _reflns_number_gt 1229 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0707P)^2^+0.1821P] 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 'refined isotropic' _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1712 _refine_ls_number_parameters 114 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.063 _refine_ls_R_factor_gt 0.041 _refine_ls_wR_factor_ref 0.115 _refine_ls_wR_factor_gt 0.103 _refine_ls_goodness_of_fit_ref 1.070 _refine_ls_restrained_S_all 1.070 _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 0.13119(4) 0.01974(5) 0.24841(2) 0.04096(17) Uani 1 1 d . . . C2 C 0.00637(17) 0.09171(19) 0.32087(12) 0.0434(4) Uani 1 1 d . . . C3 C -0.06866(15) -0.02419(17) 0.36487(9) 0.0376(4) Uani 1 1 d . . . C4 C -0.12974(15) -0.11857(18) 0.39950(10) 0.0363(3) Uani 1 1 d . . . C5 C -0.20942(17) -0.2356(2) 0.43975(10) 0.0424(4) Uani 1 1 d . . . C6 C 0.33993(17) 0.1791(2) 0.51860(10) 0.0436(4) Uani 1 1 d . . . C7 C 0.31292(15) 0.08380(19) 0.44747(10) 0.0401(4) Uani 1 1 d . . . C8 C 0.28472(16) 0.00702(18) 0.38948(10) 0.0395(4) Uani 1 1 d . . . C9 C 0.23894(19) -0.08241(19) 0.31980(10) 0.0427(4) Uani 1 1 d . . . H2A H 0.049(2) 0.158(2) 0.3614(12) 0.062(6) Uiso 1 1 d . . . H2B H -0.050(2) 0.158(2) 0.2855(14) 0.066(6) Uiso 1 1 d . . . H5A H -0.155(2) -0.282(2) 0.4826(12) 0.048(5) Uiso 1 1 d . . . H5B H -0.232(2) -0.310(2) 0.3993(13) 0.066(6) Uiso 1 1 d . . . H6A H 0.386(2) 0.266(3) 0.4994(12) 0.064(7) Uiso 1 1 d . . . H6B H 0.390(2) 0.124(3) 0.5587(13) 0.061(6) Uiso 1 1 d . . . H9B H 0.194(2) -0.169(2) 0.3394(11) 0.055(5) Uiso 1 1 d . . . H9A H 0.317(2) -0.120(2) 0.2857(14) 0.064(6) 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 0.0414(3) 0.0492(3) 0.0323(3) 0.00454(16) 0.00613(15) -0.00160(17) C2 0.0370(8) 0.0408(9) 0.0523(9) 0.0065(7) 0.0094(7) 0.0022(7) C3 0.0279(7) 0.0464(8) 0.0385(8) 0.0018(7) 0.0023(6) 0.0008(7) C4 0.0301(7) 0.0442(8) 0.0348(7) -0.0023(7) 0.0008(6) -0.0007(6) C5 0.0412(8) 0.0445(9) 0.0415(9) -0.0003(7) 0.0047(7) -0.0073(7) C6 0.0325(7) 0.0584(11) 0.0397(8) 0.0029(8) 0.0008(7) -0.0114(8) C7 0.0332(8) 0.0494(9) 0.0377(8) 0.0086(7) 0.0048(6) 0.0012(7) C8 0.0381(8) 0.0438(9) 0.0366(7) 0.0080(6) 0.0057(6) 0.0060(7) C9 0.0504(9) 0.0382(8) 0.0394(8) 0.0023(7) 0.0096(7) 0.0064(8) _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 1.8173(17) . ? S1 C9 1.8184(18) . ? C2 C3 1.465(2) . ? C2 H2A 0.98(2) . ? C2 H2B 1.00(2) . ? C3 C4 1.184(2) . ? C4 C5 1.468(2) . ? C5 C6 1.538(2) 5_556 ? C5 H5A 0.97(2) . ? C5 H5B 0.97(2) . ? C6 C7 1.460(2) . ? C6 C5 1.538(2) 5_556 ? C6 H6A 0.96(2) . ? C6 H6B 0.95(2) . ? C7 C8 1.198(2) . ? C8 C9 1.457(2) . ? C9 H9B 0.95(2) . ? C9 H9A 1.00(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 S1 C9 99.64(8) . . ? C3 C2 S1 113.45(12) . . ? C3 C2 H2A 109.0(12) . . ? S1 C2 H2A 111.1(13) . . ? C3 C2 H2B 115.3(13) . . ? S1 C2 H2B 102.9(13) . . ? H2A C2 H2B 104.6(17) . . ? C4 C3 C2 179.18(17) . . ? C3 C4 C5 177.73(17) . . ? C4 C5 C6 113.67(15) . 5_556 ? C4 C5 H5A 109.2(12) . . ? C6 C5 H5A 107.2(11) 5_556 . ? C4 C5 H5B 109.2(12) . . ? C6 C5 H5B 109.3(13) 5_556 . ? H5A C5 H5B 108.1(18) . . ? C7 C6 C5 112.81(14) . 5_556 ? C7 C6 H6A 108.3(12) . . ? C5 C6 H6A 105.4(12) 5_556 . ? C7 C6 H6B 108.9(13) . . ? C5 C6 H6B 108.1(13) 5_556 . ? H6A C6 H6B 113.3(17) . . ? C8 C7 C6 177.08(17) . . ? C7 C8 C9 175.30(17) . . ? C8 C9 S1 112.91(12) . . ? C8 C9 H9B 110.0(12) . . ? S1 C9 H9B 110.6(12) . . ? C8 C9 H9A 112.1(13) . . ? S1 C9 H9A 105.6(13) . . ? H9B C9 H9A 105.2(17) . . ? 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 C2 C3 -60.71(15) . . . . ? S1 C2 C3 C4 -55(12) . . . . ? C2 C3 C4 C5 -34(15) . . . . ? C3 C4 C5 C6 -76(4) . . . 5_556 ? C5 C6 C7 C8 6(4) 5_556 . . . ? C6 C7 C8 C9 4(5) . . . . ? C7 C8 C9 S1 48(2) . . . . ? C2 S1 C9 C8 -52.58(14) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.90 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.250 _refine_diff_density_min -0.542 _refine_diff_density_rms 0.085 #===END data_br29_6inpaper _database_code_CSD 172998 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H24 S2' _chemical_formula_weight 328.51 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'S' 'S' 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 17.03120(10) _cell_length_b 5.04950(10) _cell_length_c 22.46810(10) _cell_angle_alpha 90.00 _cell_angle_beta 106.7520(10) _cell_angle_gamma 90.00 _cell_volume 1850.23(4) _cell_formula_units_Z 4 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description polyhedron _exptl_crystal_colour colorless _exptl_crystal_size_max .56 _exptl_crystal_size_mid .20 _exptl_crystal_size_min .11 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.179 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 704 _exptl_absorpt_coefficient_mu 0.283 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.84 _exptl_absorpt_correction_T_max 0.97 _exptl_absorpt_process_details 'Blessing, Acta Cryst. (1995) A51 33-38.' _exptl_special_details ; ? ; _diffrn_ambient_temperature 200(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 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 18002 _diffrn_reflns_av_R_equivalents 0.0307 _diffrn_reflns_av_sigmaI/netI 0.0230 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 1.33 _diffrn_reflns_theta_max 27.48 _reflns_number_total 4229 _reflns_number_gt 3310 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _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^)+(0.0454P)^2^+0.5803P] 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 noref _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4229 _refine_ls_number_parameters 208 _refine_ls_number_restraints 7 _refine_ls_R_factor_all 0.0523 _refine_ls_R_factor_gt 0.0362 _refine_ls_wR_factor_ref 0.0970 _refine_ls_wR_factor_gt 0.0882 _refine_ls_goodness_of_fit_ref 1.019 _refine_ls_restrained_S_all 1.046 _refine_ls_shift/su_max 0.034 _refine_ls_shift/su_mean 0.007 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_1 S 0.79006(2) 0.67577(9) 0.160735(17) 0.03723(12) Uani 1 1 d . . . C1_1 C 0.70821(9) 0.8340(3) 0.18457(7) 0.0333(3) Uani 1 1 d . . . H1A_1 H 0.7307 0.9065 0.2270 0.040 Uiso 1 1 calc R . . H1B_1 H 0.6860 0.9835 0.1562 0.040 Uiso 1 1 calc R . . C2_1 C 0.64208(8) 0.6495(3) 0.18393(6) 0.0302(3) Uani 1 1 d . . . C3_1 C 0.59013(9) 0.4881(3) 0.18099(6) 0.0318(3) Uani 1 1 d . . . C4_1 C 0.52638(9) 0.2861(3) 0.17446(7) 0.0343(3) Uani 1 1 d . . . H4A_1 H 0.4809 0.3613 0.1883 0.041 Uiso 1 1 calc R . . H4B_1 H 0.5494 0.1347 0.2019 0.041 Uiso 1 1 calc R . . C5_1 C 0.49239(9) 0.1859(3) 0.10789(6) 0.0316(3) Uani 1 1 d . . . H5A_1 H 0.4701 0.3371 0.0801 0.038 Uiso 1 1 calc R . . H5B_1 H 0.5374 0.1060 0.0942 0.038 Uiso 1 1 calc R . . C6_1 C 0.42525(9) -0.0183(3) 0.10242(7) 0.0334(3) Uani 1 1 d . . . H6A_1 H 0.3807 0.0621 0.1166 0.040 Uiso 1 1 calc R . . H6B_1 H 0.4478 -0.1688 0.1304 0.040 Uiso 1 1 calc R . . C7_1 C 0.38899(10) -0.1238(3) 0.03600(7) 0.0397(4) Uani 1 1 d . . . H7A_1 H 0.4337 -0.1998 0.0214 0.048 Uiso 1 1 calc R . . H7B_1 H 0.3499 -0.2681 0.0367 0.048 Uiso 1 1 calc R . . C8_1 C 0.34654(9) 0.0805(3) -0.00808(7) 0.0349(3) Uani 1 1 d . . . C9_1 C 0.31152(9) 0.2491(3) -0.04250(7) 0.0340(3) Uani 1 1 d . . . C10_1 C 0.26922(10) 0.4545(3) -0.08588(7) 0.0359(3) Uani 1 1 d . . . H10A_1 H 0.3103 0.5812 -0.0924 0.043 Uiso 1 1 calc R . . H10B_1 H 0.2321 0.5530 -0.0671 0.043 Uiso 1 1 calc R . . S1_2 S 0.27743(3) 0.54656(11) 0.15147(2) 0.05437(15) Uani 1 1 d . . . C1_2 C 0.20643(11) 0.7309(4) 0.18228(8) 0.0456(4) Uani 1 1 d . . . H1A_2 H 0.2370 0.8125 0.2223 0.055 Uiso 1 1 calc R . . H1B_2 H 0.1819 0.8755 0.1531 0.055 Uiso 1 1 calc R . . C2_2 C 0.14108(10) 0.5656(3) 0.19199(7) 0.0383(4) Uani 1 1 d . . . C3_2 C 0.08801(10) 0.4249(4) 0.19803(7) 0.0411(4) Uani 1 1 d D A . C4_2 C 0.02164(12) 0.2539(5) 0.20426(8) 0.0584(5) Uani 1 1 d D . . H4A_2 H -0.0023 0.3300 0.2357 0.070 Uiso 0.798(4) 1 calc PR A 1 H4B_2 H 0.0443 0.0775 0.2192 0.070 Uiso 0.798(4) 1 calc PR A 1 H4C_2 H -0.0263 0.3650 0.2042 0.070 Uiso 0.202(4) 1 calc PR A 2 H4D_2 H 0.0396 0.1613 0.2448 0.070 Uiso 0.202(4) 1 calc PR A 2 C5_2 C -0.04814(12) 0.2203(4) 0.14081(10) 0.0418(6) Uani 0.798(4) 1 d PD A 1 H5A_2 H -0.0959 0.1300 0.1485 0.050 Uiso 0.798(4) 1 calc PR A 1 H5B_2 H -0.0662 0.3970 0.1230 0.050 Uiso 0.798(4) 1 calc PR A 1 C6_2 C -0.01785(12) 0.0611(4) 0.09504(9) 0.0407(6) Uani 0.798(4) 1 d PD A 1 H6A_2 H 0.0091 -0.1023 0.1154 0.049 Uiso 0.798(4) 1 calc PR A 1 H6B_2 H 0.0233 0.1656 0.0817 0.049 Uiso 0.798(4) 1 calc PR A 1 C7_2 C -0.08832(12) -0.0124(4) 0.03828(9) 0.0598(5) Uani 1 1 d D . . H7A_2 H -0.0670 -0.1408 0.0134 0.072 Uiso 0.798(4) 1 calc PR A 1 H7B_2 H -0.1301 -0.1061 0.0532 0.072 Uiso 0.798(4) 1 calc PR A 1 H7C_2 H -0.0439 -0.0987 0.0250 0.072 Uiso 0.202(4) 1 calc PR A 2 H7D_2 H -0.1263 -0.1461 0.0467 0.072 Uiso 0.202(4) 1 calc PR A 2 C8_2 C -0.13015(11) 0.2005(4) -0.00381(8) 0.0460(4) Uani 1 1 d D A . C9_2 C -0.16427(11) 0.3715(4) -0.03779(8) 0.0448(4) Uani 1 1 d . . . C10_2 C -0.20601(11) 0.5793(4) -0.08065(8) 0.0488(4) Uani 1 1 d . . . H10A_2 H -0.1643 0.6896 -0.0918 0.059 Uiso 1 1 calc R . . H10B_2 H -0.2362 0.6946 -0.0591 0.059 Uiso 1 1 calc R . . C5B_2 C -0.0046(5) 0.0477(15) 0.1523(3) 0.037(2) Uiso 0.202(4) 1 d PD A 2 H5B1_2 H 0.0433 -0.0352 0.1431 0.045 Uiso 0.202(4) 1 calc PR A 2 H5B2_2 H -0.0395 -0.0917 0.1626 0.045 Uiso 0.202(4) 1 calc PR A 2 C6B_2 C -0.0520(4) 0.2185(15) 0.0999(3) 0.032(2) Uiso 0.202(4) 1 d PD A 2 H6B1_2 H -0.0163 0.3538 0.0891 0.039 Uiso 0.202(4) 1 calc PR A 2 H6B2_2 H -0.0981 0.3078 0.1103 0.039 Uiso 0.202(4) 1 calc PR A 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1_1 0.02783(18) 0.0519(3) 0.02980(19) 0.00265(17) 0.00483(14) -0.00116(17) C1_1 0.0353(7) 0.0317(8) 0.0304(7) -0.0032(6) 0.0053(6) -0.0032(6) C2_1 0.0307(7) 0.0321(8) 0.0261(7) -0.0014(6) 0.0058(5) 0.0040(6) C3_1 0.0318(7) 0.0351(8) 0.0267(7) -0.0008(6) 0.0055(6) 0.0040(6) C4_1 0.0345(7) 0.0373(8) 0.0321(7) -0.0005(6) 0.0111(6) -0.0040(6) C5_1 0.0325(7) 0.0324(8) 0.0297(7) 0.0018(6) 0.0084(6) -0.0007(6) C6_1 0.0366(8) 0.0307(8) 0.0306(7) 0.0043(6) 0.0060(6) -0.0029(6) C7_1 0.0497(9) 0.0284(8) 0.0361(8) -0.0003(7) 0.0044(7) -0.0034(7) C8_1 0.0404(8) 0.0337(8) 0.0278(7) -0.0052(6) 0.0054(6) -0.0065(7) C9_1 0.0386(8) 0.0361(8) 0.0266(7) -0.0040(6) 0.0085(6) -0.0058(7) C10_1 0.0423(8) 0.0371(9) 0.0282(7) -0.0013(6) 0.0099(6) 0.0017(7) S1_2 0.0367(2) 0.0719(4) 0.0541(3) 0.0102(2) 0.0125(2) -0.0053(2) C1_2 0.0511(10) 0.0415(10) 0.0398(9) -0.0026(7) 0.0063(7) -0.0101(8) C2_2 0.0435(9) 0.0390(9) 0.0295(8) -0.0015(7) 0.0059(7) 0.0021(7) C3_2 0.0465(9) 0.0475(10) 0.0293(8) -0.0038(7) 0.0108(7) -0.0014(8) C4_2 0.0672(12) 0.0759(14) 0.0420(10) -0.0091(9) 0.0315(9) -0.0211(11) C5_2 0.0366(11) 0.0446(13) 0.0490(14) -0.0047(10) 0.0198(9) -0.0037(9) C6_2 0.0402(11) 0.0389(12) 0.0413(12) -0.0008(9) 0.0088(9) 0.0054(9) C7_2 0.0575(11) 0.0697(14) 0.0440(10) 0.0101(9) 0.0016(9) -0.0186(10) C8_2 0.0506(10) 0.0524(11) 0.0350(8) -0.0061(8) 0.0127(7) -0.0169(9) C9_2 0.0528(10) 0.0469(10) 0.0387(9) -0.0081(8) 0.0196(8) -0.0140(8) C10_2 0.0561(10) 0.0463(10) 0.0497(10) -0.0007(8) 0.0246(8) -0.0038(8) _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_1 C1_1 1.8162(15) . ? S1_1 C10_1 1.8172(15) 3_665 ? C1_1 C2_1 1.459(2) . ? C2_1 C3_1 1.191(2) . ? C3_1 C4_1 1.466(2) . ? C4_1 C5_1 1.526(2) . ? C5_1 C6_1 1.518(2) . ? C6_1 C7_1 1.536(2) . ? C7_1 C8_1 1.468(2) . ? C8_1 C9_1 1.189(2) . ? C9_1 C10_1 1.463(2) . ? C10_1 S1_1 1.8172(15) 3_665 ? S1_2 C1_2 1.8139(19) . ? S1_2 C10_2 1.8166(19) 3_565 ? C1_2 C2_2 1.457(2) . ? C2_2 C3_2 1.188(2) . ? C3_2 C4_2 1.461(2) . ? C4_2 C5B_2 1.531(7) . ? C4_2 C5_2 1.580(3) . ? C5_2 C6_2 1.508(3) . ? C6_2 C7_2 1.524(3) . ? C7_2 C8_2 1.473(3) . ? C7_2 C6B_2 1.779(8) . ? C8_2 C9_2 1.188(3) . ? C9_2 C10_2 1.462(3) . ? C10_2 S1_2 1.8166(19) 3_565 ? C5B_2 C6B_2 1.495(10) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1_1 S1_1 C10_1 99.39(7) . 3_665 ? C2_1 C1_1 S1_1 111.85(11) . . ? C3_1 C2_1 C1_1 175.65(15) . . ? C2_1 C3_1 C4_1 177.32(15) . . ? C3_1 C4_1 C5_1 112.93(12) . . ? C6_1 C5_1 C4_1 111.63(12) . . ? C5_1 C6_1 C7_1 113.36(12) . . ? C8_1 C7_1 C6_1 113.17(13) . . ? C9_1 C8_1 C7_1 178.22(17) . . ? C8_1 C9_1 C10_1 178.77(17) . . ? C9_1 C10_1 S1_1 113.30(11) . 3_665 ? C1_2 S1_2 C10_2 99.33(8) . 3_565 ? C2_2 C1_2 S1_2 112.66(12) . . ? C3_2 C2_2 C1_2 177.45(18) . . ? C2_2 C3_2 C4_2 178.84(19) . . ? C3_2 C4_2 C5B_2 113.1(3) . . ? C3_2 C4_2 C5_2 112.23(15) . . ? C5B_2 C4_2 C5_2 42.4(3) . . ? C6_2 C5_2 C4_2 110.86(17) . . ? C5_2 C6_2 C7_2 111.02(17) . . ? C8_2 C7_2 C6_2 118.56(18) . . ? C8_2 C7_2 C6B_2 91.0(3) . . ? C6_2 C7_2 C6B_2 34.5(2) . . ? C9_2 C8_2 C7_2 179.7(2) . . ? C8_2 C9_2 C10_2 178.88(19) . . ? C9_2 C10_2 S1_2 113.67(13) . 3_565 ? C6B_2 C5B_2 C4_2 100.4(5) . . ? C5B_2 C6B_2 C7_2 102.9(5) . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.371 _refine_diff_density_min -0.279 _refine_diff_density_rms 0.039 #===END data_dwe14_14inpaper _database_code_CSD 172999 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H28 S8' _chemical_formula_weight 548.92 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 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 9.8778(2) _cell_length_b 9.5740(2) _cell_length_c 28.60500(10) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2705.18(8) _cell_formula_units_Z 4 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description polyhedron _exptl_crystal_colour colorless _exptl_crystal_size_max .36 _exptl_crystal_size_mid .32 _exptl_crystal_size_min .28 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.348 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1152 _exptl_absorpt_coefficient_mu 0.669 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.69 _exptl_absorpt_correction_T_max 0.86 _exptl_absorpt_process_details 'Blessing, Acta Cryst. (1995) A51 33-38.' _exptl_special_details ; ? ; _diffrn_ambient_temperature 200(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 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 25957 _diffrn_reflns_av_R_equivalents 0.0396 _diffrn_reflns_av_sigmaI/netI 0.0175 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -37 _diffrn_reflns_limit_l_max 37 _diffrn_reflns_theta_min 2.51 _diffrn_reflns_theta_max 27.49 _reflns_number_total 3097 _reflns_number_gt 2678 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _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^)+(0.0309P)^2^+0.9258P] 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 refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3097 _refine_ls_number_parameters 192 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0365 _refine_ls_R_factor_gt 0.0291 _refine_ls_wR_factor_ref 0.0731 _refine_ls_wR_factor_gt 0.0693 _refine_ls_goodness_of_fit_ref 1.115 _refine_ls_restrained_S_all 1.115 _refine_ls_shift/su_max 0.008 _refine_ls_shift/su_mean 0.002 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 0.25877(5) 0.02826(5) 0.422460(16) 0.04852(13) Uani 1 1 d . . . S2 S 0.55543(5) 0.07288(5) 0.248577(14) 0.04178(12) Uani 1 1 d . . . S3 S 0.86730(4) 0.18556(4) 0.359569(15) 0.03818(11) Uani 1 1 d . . . S4 S 0.48041(4) 0.28241(5) 0.497414(15) 0.04327(12) Uani 1 1 d . . . C1 C 0.35581(17) -0.09018(19) 0.44971(6) 0.0406(4) Uani 1 1 d . . . C2 C 0.18612(18) -0.0742(2) 0.37489(7) 0.0445(4) Uani 1 1 d . . . H2A H 0.124(2) -0.011(2) 0.3609(7) 0.054(6) Uiso 1 1 d . . . H2B H 0.142(2) -0.150(2) 0.3878(7) 0.055(6) Uiso 1 1 d . . . C3 C 0.28683(17) -0.12563(17) 0.33888(6) 0.0366(3) Uani 1 1 d . . . H3A H 0.3437(18) -0.2010(19) 0.3522(6) 0.040(5) Uiso 1 1 d . . . H3B H 0.2348(18) -0.1687(19) 0.3140(6) 0.041(5) Uiso 1 1 d . . . C4 C 0.37390(17) -0.01039(16) 0.31789(6) 0.0339(3) Uani 1 1 d . . . H4A H 0.4371(17) 0.0250(18) 0.3399(6) 0.036(4) Uiso 1 1 d . . . H4B H 0.3186(18) 0.0728(19) 0.3082(6) 0.040(5) Uiso 1 1 d . . . C5 C 0.45111(17) -0.06127(16) 0.27540(5) 0.0334(3) Uani 1 1 d . . . H5A H 0.3874(19) -0.0886(18) 0.2500(6) 0.044(5) Uiso 1 1 d . . . H5B H 0.5055(19) -0.137(2) 0.2811(6) 0.045(5) Uiso 1 1 d . . . C6 C 0.66750(17) 0.10910(17) 0.29093(6) 0.0366(3) Uani 1 1 d . . . C7 C 0.74973(17) 0.14315(16) 0.31967(5) 0.0358(3) Uani 1 1 d . . . C8 C 0.77790(17) 0.31298(16) 0.39530(6) 0.0339(3) Uani 1 1 d . . . H8A H 0.7407(18) 0.3813(19) 0.3750(6) 0.040(5) Uiso 1 1 d . . . H8B H 0.8450(19) 0.354(2) 0.4135(7) 0.046(5) Uiso 1 1 d . . . C9 C 0.66815(16) 0.24799(16) 0.42543(5) 0.0323(3) Uani 1 1 d . . . H9A H 0.7021(18) 0.174(2) 0.4441(6) 0.042(5) Uiso 1 1 d . . . H9B H 0.5961(19) 0.2107(19) 0.4060(7) 0.042(5) Uiso 1 1 d . . . C10 C 0.60760(17) 0.35557(17) 0.45846(6) 0.0361(3) Uani 1 1 d . . . H10A H 0.5581(17) 0.4298(19) 0.4427(6) 0.038(5) Uiso 1 1 d . . . H10B H 0.6776(18) 0.3983(18) 0.4777(6) 0.036(4) Uiso 1 1 d . . . C11 C 0.57461(17) 0.16890(18) 0.52827(5) 0.0387(4) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.0624(3) 0.0432(2) 0.0400(2) 0.00310(18) 0.0133(2) 0.0135(2) S2 0.0546(3) 0.0426(2) 0.02810(19) 0.00623(17) 0.00018(17) -0.00784(19) S3 0.02928(19) 0.0430(2) 0.0422(2) 0.00203(17) 0.00441(16) -0.00127(16) S4 0.0340(2) 0.0586(3) 0.0373(2) -0.00592(19) 0.00106(16) 0.00793(19) C1 0.0402(9) 0.0475(9) 0.0340(8) 0.0012(7) 0.0126(7) -0.0012(7) C2 0.0334(9) 0.0503(10) 0.0497(10) 0.0108(8) 0.0054(8) 0.0055(8) C3 0.0352(8) 0.0330(8) 0.0415(9) 0.0028(7) -0.0001(7) -0.0001(7) C4 0.0369(8) 0.0297(8) 0.0350(8) -0.0021(6) -0.0002(7) -0.0004(7) C5 0.0432(9) 0.0275(7) 0.0296(7) 0.0000(6) -0.0014(6) -0.0006(7) C6 0.0401(8) 0.0354(8) 0.0344(8) -0.0001(6) 0.0087(7) -0.0011(7) C7 0.0397(8) 0.0334(8) 0.0342(8) 0.0038(6) 0.0105(7) -0.0042(7) C8 0.0381(8) 0.0305(7) 0.0331(8) 0.0020(6) -0.0038(6) -0.0033(6) C9 0.0332(8) 0.0329(8) 0.0307(7) -0.0009(6) -0.0017(6) -0.0002(6) C10 0.0397(8) 0.0366(8) 0.0319(8) -0.0021(7) -0.0052(7) 0.0039(7) C11 0.0396(8) 0.0452(9) 0.0314(8) -0.0050(7) 0.0055(7) -0.0035(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 C1 1.6770(19) . ? S1 C2 1.824(2) . ? S2 C6 1.6773(17) . ? S2 C5 1.8166(16) . ? S3 C7 1.6782(17) . ? S3 C8 1.8201(17) . ? S4 C11 1.6809(18) . ? S4 C10 1.8195(17) . ? C1 C11 1.199(2) 5_656 ? C2 C3 1.514(2) . ? C3 C4 1.522(2) . ? C4 C5 1.515(2) . ? C6 C7 1.201(2) . ? C8 C9 1.518(2) . ? C9 C10 1.520(2) . ? C11 C1 1.199(2) 5_656 ? 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 C1 S1 C2 102.00(9) . . ? C6 S2 C5 102.44(8) . . ? C7 S3 C8 102.03(8) . . ? C11 S4 C10 100.85(8) . . ? C11 C1 S1 175.58(16) 5_656 . ? C3 C2 S1 115.08(13) . . ? C2 C3 C4 113.81(14) . . ? C5 C4 C3 111.57(13) . . ? C4 C5 S2 113.39(11) . . ? C7 C6 S2 175.60(15) . . ? C6 C7 S3 178.07(16) . . ? C9 C8 S3 112.99(11) . . ? C8 C9 C10 110.86(13) . . ? C9 C10 S4 113.05(12) . . ? C1 C11 S4 178.47(16) 5_656 . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.227 _refine_diff_density_min -0.271 _refine_diff_density_rms 0.055 #===END data_dwe38_15inpaper _database_code_CSD 173000 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H16 S8' _chemical_formula_weight 464.77 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 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 11.6465(4) _cell_length_b 9.3011(3) _cell_length_c 10.0017(4) _cell_angle_alpha 90.00 _cell_angle_beta 101.1960(10) _cell_angle_gamma 90.00 _cell_volume 1062.82(7) _cell_formula_units_Z 2 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description polyhedron _exptl_crystal_colour colorless _exptl_crystal_size_max .17 _exptl_crystal_size_mid .14 _exptl_crystal_size_min .06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.452 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 480 _exptl_absorpt_coefficient_mu 0.837 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.44 _exptl_absorpt_correction_T_max 0.96 _exptl_absorpt_process_details 'Blessing, Acta Cryst. (1995) A51 33-38.' _exptl_special_details ; ? ; _diffrn_ambient_temperature 200(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 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8114 _diffrn_reflns_av_R_equivalents 0.0556 _diffrn_reflns_av_sigmaI/netI 0.0363 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 1.78 _diffrn_reflns_theta_max 24.09 _reflns_number_total 1686 _reflns_number_gt 1263 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _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^)+(0.0579P)^2^+0.5302P] 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 noref _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1686 _refine_ls_number_parameters 109 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0613 _refine_ls_R_factor_gt 0.0395 _refine_ls_wR_factor_ref 0.1101 _refine_ls_wR_factor_gt 0.0992 _refine_ls_goodness_of_fit_ref 1.049 _refine_ls_restrained_S_all 1.049 _refine_ls_shift/su_max 0.007 _refine_ls_shift/su_mean 0.002 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 0.21200(9) 0.21410(10) 0.01342(10) 0.0504(3) Uani 1 1 d . . . S2 S 0.02292(8) -0.15881(11) -0.22996(10) 0.0478(3) Uani 1 1 d . . . S3 S 0.26071(9) -0.12306(11) -0.52266(9) 0.0478(3) Uani 1 1 d . . . S4 S 0.54117(9) 0.11242(10) -0.22491(12) 0.0554(3) Uani 1 1 d . . . C2 C 0.1397(3) 0.0800(4) -0.0783(4) 0.0420(9) Uani 1 1 d . . . C3 C 0.0896(3) -0.0186(4) -0.1425(3) 0.0417(9) Uani 1 1 d . . . C5 C 0.1329(3) -0.2062(4) -0.3322(4) 0.0418(9) Uani 1 1 d . . . H5A H 0.2112 -0.2111 -0.2723 0.050 Uiso 1 1 calc R . . H5B H 0.1146 -0.3021 -0.3738 0.050 Uiso 1 1 calc R . . C6 C 0.1347(3) -0.0977(4) -0.4415(4) 0.0414(9) Uani 1 1 d . . . H6A H 0.1374 0.0001 -0.4018 0.050 Uiso 1 1 calc R . . H6B H 0.0618 -0.1059 -0.5111 0.050 Uiso 1 1 calc R . . C8 C 0.3654(3) -0.0434(4) -0.4086(4) 0.0423(9) Uani 1 1 d . . . C9 C 0.4417(3) 0.0128(4) -0.3287(4) 0.0434(9) Uani 1 1 d . . . C11 C 0.6150(3) -0.0177(4) -0.1007(4) 0.0490(10) Uani 1 1 d . . . H11A H 0.6563 0.0347 -0.0193 0.059 Uiso 1 1 calc R . . H11B H 0.5554 -0.0800 -0.0717 0.059 Uiso 1 1 calc R . . C12 C 0.7014(3) -0.1108(4) -0.1534(4) 0.0428(9) Uani 1 1 d . . . H12A H 0.7539 -0.0500 -0.1964 0.051 Uiso 1 1 calc R . . H12B H 0.6594 -0.1773 -0.2235 0.051 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 0.0595(7) 0.0337(5) 0.0541(6) -0.0041(4) 0.0020(5) 0.0072(5) S2 0.0371(5) 0.0551(6) 0.0489(6) 0.0001(5) 0.0027(4) -0.0069(4) S3 0.0522(6) 0.0504(6) 0.0389(5) -0.0037(4) 0.0044(5) 0.0020(5) S4 0.0406(6) 0.0356(6) 0.0838(8) -0.0008(5) -0.0028(5) -0.0002(4) C2 0.040(2) 0.041(2) 0.043(2) 0.0023(18) 0.0059(18) 0.0084(18) C3 0.0325(19) 0.052(2) 0.039(2) 0.0105(19) 0.0027(17) 0.0113(18) C5 0.040(2) 0.035(2) 0.048(2) 0.0007(16) -0.0007(17) -0.0002(16) C6 0.040(2) 0.037(2) 0.042(2) 0.0029(16) -0.0059(17) 0.0041(16) C8 0.046(2) 0.0333(19) 0.048(2) 0.0069(17) 0.0090(19) 0.0037(18) C9 0.040(2) 0.035(2) 0.055(2) 0.0044(18) 0.0094(19) 0.0060(17) C11 0.040(2) 0.050(2) 0.055(2) -0.0075(19) 0.0048(19) 0.0023(19) C12 0.041(2) 0.041(2) 0.045(2) -0.0058(17) 0.0028(17) -0.0001(17) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 C2 1.675(4) . ? S1 C12 1.831(4) 3_655 ? S2 C3 1.675(4) . ? S2 C5 1.841(4) . ? S3 C8 1.673(4) . ? S3 C6 1.825(4) . ? S4 C9 1.677(4) . ? S4 C11 1.826(4) . ? C2 C3 1.203(5) . ? C5 C6 1.491(5) . ? C8 C9 1.194(5) . ? C11 C12 1.498(5) . ? C12 S1 1.832(4) 3_655 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 S1 C12 99.89(17) . 3_655 ? C3 S2 C5 100.02(17) . . ? C8 S3 C6 100.49(17) . . ? C9 S4 C11 103.46(18) . . ? C3 C2 S1 178.4(3) . . ? C2 C3 S2 178.5(3) . . ? C6 C5 S2 110.8(2) . . ? C5 C6 S3 111.4(2) . . ? C9 C8 S3 178.7(4) . . ? C8 C9 S4 172.5(3) . . ? C12 C11 S4 113.8(3) . . ? C11 C12 S1 110.0(2) . 3_655 ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 24.09 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.427 _refine_diff_density_min -0.300 _refine_diff_density_rms 0.060 #===END _eof # End of Crystallographic Information File