Supplementary Material (ESI) for Chemical Communications This journal is © The Royal Society of Chemistry 2002 data_global _audit_creation_method 'SHELXTL plus manual editing' _journal_coden_Cambridge 182 loop_ _publ_author_name 'Andrew Holmes' 'Andrew Bond' 'Joseph Frey' _publ_contact_author_name 'Prof Andrew Holmes' _publ_contact_author_address ; Department of Chemistry University of Cambridge Lensfield Road Cambridge Cambs. CB2 1EW UNITED KINGDOM ; _publ_contact_author_email 'ABH1@CAM.AC.UK' _publ_requested_journal 'Chemical Communications' _publ_section_title ; Improved synthesis of dithieno[3,2-b:2',3'-d]thiophene (DTT) and derivatives for cross coupling ; data_ah0013 _database_code_CSD 190974 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H18 Br2 S3 Si2' _chemical_formula_sum 'C14 H18 Br2 S3 Si2' _chemical_formula_weight 498.46 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' 'Br' 'Br' -0.2901 2.4595 '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' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 12.9980(10) _cell_length_b 13.0198(9) _cell_length_c 13.4649(10) _cell_angle_alpha 75.266(4) _cell_angle_beta 69.243(4) _cell_angle_gamma 74.417(4) _cell_volume 2020.2(3) _cell_formula_units_Z 4 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 16945 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 25.03 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.639 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 992 _exptl_absorpt_coefficient_mu 4.433 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.544 _exptl_absorpt_correction_T_max 0.766 _exptl_absorpt_process_details 'Sortav Blessing (1995)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.7107 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method 'Thin slice \w and \f scans' _diffrn_standards_number 0 _diffrn_reflns_number 15851 _diffrn_reflns_av_R_equivalents 0.1176 _diffrn_reflns_av_sigmaI/netI 0.1387 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.77 _diffrn_reflns_theta_max 25.03 _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 25.03 _diffrn_measured_fraction_theta_full 0.987 _reflns_number_total 7043 _reflns_number_gt 4457 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V. 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction ; HKL Denzo and Scalepack (Otwinowski & Minor 1997) ; _computing_structure_solution 'SIR-92 (Altomare et al. 1994)' _computing_structure_refinement 'SHELXTL v6.12 (Bruker AXS, 2001)' _computing_publication_material 'SHELXTL v6.12 (Bruker AXS, 2001)' _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^)+(0.0725P)^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 7043 _refine_ls_number_parameters 392 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1118 _refine_ls_R_factor_gt 0.0566 _refine_ls_wR_factor_ref 0.1572 _refine_ls_wR_factor_gt 0.1269 _refine_ls_goodness_of_fit_ref 1.015 _refine_ls_restrained_S_all 1.015 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.569 _refine_diff_density_min -1.044 _refine_diff_density_rms 0.154 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 Br1_1 Br 0.22797(7) 0.78273(6) -0.01137(6) 0.0472(3) Uani 1 1 d . . . Br2_1 Br 0.06042(7) 0.06679(6) 0.05854(6) 0.0404(2) Uani 1 1 d . . . S1_1 S 0.19692(16) 0.57034(14) -0.04731(14) 0.0339(4) Uani 1 1 d . . . S2_1 S 0.12692(15) 0.28975(14) -0.02030(14) 0.0325(4) Uani 1 1 d . . . S3_1 S 0.00593(15) 0.43240(14) 0.25430(13) 0.0311(4) Uani 1 1 d . . . Si1_1 Si 0.06042(18) 0.69857(16) 0.26247(15) 0.0349(5) Uani 1 1 d . . . Si2_1 Si -0.06616(17) 0.15617(16) 0.31519(15) 0.0316(5) Uani 1 1 d . . . C1_1 C 0.1673(6) 0.6563(5) 0.0429(5) 0.0290(16) Uani 1 1 d . . . C2_1 C 0.1062(6) 0.6234(5) 0.1475(5) 0.0304(16) Uani 1 1 d . . . C3_1 C 0.0801(6) 0.5213(5) 0.1508(5) 0.0280(16) Uani 1 1 d . . . C4_1 C 0.1242(6) 0.4816(5) 0.0548(5) 0.0277(15) Uani 1 1 d . . . C5_1 C 0.0585(6) 0.2005(6) 0.0888(6) 0.0335(17) Uani 1 1 d . . . C6_1 C 0.0138(5) 0.2346(5) 0.1849(5) 0.0305(16) Uani 1 1 d . . . C7_1 C 0.0375(5) 0.3406(5) 0.1683(5) 0.0271(15) Uani 1 1 d . . . C8_1 C 0.0985(6) 0.3799(5) 0.0643(5) 0.0281(15) Uani 1 1 d . . . C9_1 C 0.1830(7) 0.7430(7) 0.2692(7) 0.054(2) Uani 1 1 d . . . H9A_1 H 0.2038 0.8017 0.2085 0.080(5) Uiso 1 1 calc R . . H9B_1 H 0.2467 0.6817 0.2653 0.080(5) Uiso 1 1 calc R . . H9C_1 H 0.1627 0.7688 0.3372 0.080(5) Uiso 1 1 calc R . . C10_1 C -0.0573(7) 0.8129(6) 0.2421(7) 0.052(2) Uani 1 1 d . . . H10A_1 H -0.0305 0.8614 0.1738 0.080(5) Uiso 1 1 calc R . . H10B_1 H -0.0845 0.8532 0.3018 0.080(5) Uiso 1 1 calc R . . H10C_1 H -0.1186 0.7839 0.2399 0.080(5) Uiso 1 1 calc R . . C11_1 C 0.0041(8) 0.6100(6) 0.3915(6) 0.053(2) Uani 1 1 d . . . H11A_1 H 0.0624 0.5465 0.4025 0.080(5) Uiso 1 1 calc R . . H11B_1 H -0.0605 0.5863 0.3893 0.080(5) Uiso 1 1 calc R . . H11C_1 H -0.0196 0.6501 0.4509 0.080(5) Uiso 1 1 calc R . . C12_1 C -0.1972(7) 0.1399(7) 0.2990(7) 0.053(2) Uani 1 1 d . . . H12A_1 H -0.2410 0.2114 0.2788 0.080(5) Uiso 1 1 calc R . . H12B_1 H -0.2417 0.1028 0.3673 0.080(5) Uiso 1 1 calc R . . H12C_1 H -0.1779 0.0970 0.2425 0.080(5) Uiso 1 1 calc R . . C13_1 C 0.0200(7) 0.0218(6) 0.3496(6) 0.048(2) Uani 1 1 d . . . H13A_1 H 0.0416 -0.0189 0.2909 0.080(5) Uiso 1 1 calc R . . H13B_1 H -0.0237 -0.0183 0.4163 0.080(5) Uiso 1 1 calc R . . H13C_1 H 0.0876 0.0314 0.3598 0.080(5) Uiso 1 1 calc R . . C14_1 C -0.0989(7) 0.2304(7) 0.4271(6) 0.051(2) Uani 1 1 d . . . H14A_1 H -0.1465 0.3013 0.4129 0.080(5) Uiso 1 1 calc R . . H14B_1 H -0.0290 0.2402 0.4324 0.080(5) Uiso 1 1 calc R . . H14C_1 H -0.1385 0.1887 0.4951 0.080(5) Uiso 1 1 calc R . . Br1_2 Br -0.30392(8) -0.04182(9) -0.38779(7) 0.0714(4) Uani 1 1 d . . . Br2_2 Br -0.38810(7) -0.09414(7) 0.38146(6) 0.0518(3) Uani 1 1 d . . . S1_2 S -0.32518(17) -0.00289(17) -0.16520(16) 0.0461(5) Uani 1 1 d . . . S2_2 S -0.36097(17) -0.02238(16) 0.13887(15) 0.0421(5) Uani 1 1 d . . . S3_2 S -0.42035(16) -0.27968(15) 0.04915(14) 0.0344(5) Uani 1 1 d . . . Si1_2 Si -0.3882(2) -0.2939(2) -0.23758(18) 0.0463(6) Uani 1 1 d . . . Si2_2 Si -0.44834(18) -0.33357(17) 0.34538(16) 0.0371(5) Uani 1 1 d . . . C1_2 C -0.3346(6) -0.0901(7) -0.2381(6) 0.044(2) Uani 1 1 d . . . C2_2 C -0.3660(6) -0.1864(6) -0.1801(6) 0.0375(18) Uani 1 1 d . . . C3_2 C -0.3821(6) -0.1854(6) -0.0689(5) 0.0334(17) Uani 1 1 d . . . C4_2 C -0.3642(6) -0.0943(6) -0.0479(6) 0.0327(17) Uani 1 1 d . . . C5_2 C -0.3918(6) -0.1211(6) 0.2529(5) 0.0361(18) Uani 1 1 d . . . C6_2 C -0.4161(6) -0.2120(6) 0.2376(6) 0.0359(18) Uani 1 1 d . . . C7_2 C -0.4073(6) -0.1970(5) 0.1243(5) 0.0298(16) Uani 1 1 d . . . C8_2 C -0.3771(6) -0.1010(5) 0.0622(6) 0.0329(17) Uani 1 1 d . . . C9_2 C -0.5127(7) -0.2358(7) -0.2880(7) 0.053(2) Uani 1 1 d . . . H9A_2 H -0.5005 -0.1690 -0.3402 0.080(5) Uiso 1 1 calc R . . H9B_2 H -0.5800 -0.2198 -0.2273 0.080(5) Uiso 1 1 calc R . . H9C_2 H -0.5226 -0.2883 -0.3231 0.080(5) Uiso 1 1 calc R . . C10_2 C -0.2625(8) -0.3349(10) -0.3502(8) 0.087(4) Uani 1 1 d . . . H10A_2 H -0.2583 -0.2771 -0.4136 0.080(5) Uiso 1 1 calc R . . H10B_2 H -0.2677 -0.4014 -0.3679 0.080(5) Uiso 1 1 calc R . . H10C_2 H -0.1949 -0.3477 -0.3286 0.080(5) Uiso 1 1 calc R . . C11_2 C -0.4141(9) -0.4129(7) -0.1288(7) 0.069(3) Uani 1 1 d . . . H11A_2 H -0.4851 -0.3933 -0.0730 0.080(5) Uiso 1 1 calc R . . H11B_2 H -0.3527 -0.4361 -0.0969 0.080(5) Uiso 1 1 calc R . . H11C_2 H -0.4181 -0.4723 -0.1589 0.080(5) Uiso 1 1 calc R . . C12_2 C -0.5728(7) -0.2915(7) 0.4554(6) 0.058(2) Uani 1 1 d . . . H12A_2 H -0.5559 -0.2441 0.4912 0.080(5) Uiso 1 1 calc R . . H12B_2 H -0.5947 -0.3556 0.5078 0.080(5) Uiso 1 1 calc R . . H12C_2 H -0.6346 -0.2522 0.4263 0.080(5) Uiso 1 1 calc R . . C13_2 C -0.3244(8) -0.3960(7) 0.3938(7) 0.059(2) Uani 1 1 d . . . H13A_2 H -0.2599 -0.4201 0.3338 0.080(5) Uiso 1 1 calc R . . H13B_2 H -0.3411 -0.4583 0.4512 0.080(5) Uiso 1 1 calc R . . H13C_2 H -0.3067 -0.3426 0.4218 0.080(5) Uiso 1 1 calc R . . C14_2 C -0.4798(8) -0.4329(6) 0.2888(6) 0.053(2) Uani 1 1 d . . . H14A_2 H -0.4131 -0.4592 0.2317 0.080(5) Uiso 1 1 calc R . . H14B_2 H -0.5417 -0.3981 0.2585 0.080(5) Uiso 1 1 calc R . . H14C_2 H -0.5013 -0.4940 0.3460 0.080(5) 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 Br1_1 0.0679(6) 0.0369(5) 0.0352(4) -0.0014(3) -0.0053(4) -0.0268(4) Br2_1 0.0521(5) 0.0401(5) 0.0368(4) -0.0161(3) -0.0077(4) -0.0211(4) S1_1 0.0447(11) 0.0326(10) 0.0233(9) -0.0034(7) -0.0062(8) -0.0129(9) S2_1 0.0373(10) 0.0366(10) 0.0262(9) -0.0116(8) -0.0051(8) -0.0123(9) S3_1 0.0403(10) 0.0305(10) 0.0246(9) -0.0079(7) -0.0046(8) -0.0149(8) Si1_1 0.0505(13) 0.0290(11) 0.0260(11) -0.0057(8) -0.0065(9) -0.0156(10) Si2_1 0.0348(11) 0.0350(11) 0.0290(11) -0.0057(8) -0.0078(9) -0.0163(9) C1_1 0.040(4) 0.024(4) 0.024(4) -0.003(3) -0.010(3) -0.008(3) C2_1 0.034(4) 0.027(4) 0.036(4) -0.008(3) -0.015(3) -0.007(3) C3_1 0.038(4) 0.025(4) 0.018(4) 0.000(3) -0.004(3) -0.012(3) C4_1 0.031(4) 0.030(4) 0.021(4) -0.001(3) -0.009(3) -0.007(3) C5_1 0.035(4) 0.037(4) 0.036(4) -0.008(3) -0.011(3) -0.018(4) C6_1 0.028(4) 0.038(4) 0.029(4) -0.010(3) -0.007(3) -0.013(3) C7_1 0.028(4) 0.033(4) 0.020(4) -0.006(3) -0.005(3) -0.009(3) C8_1 0.030(4) 0.029(4) 0.026(4) -0.010(3) -0.008(3) -0.003(3) C9_1 0.050(5) 0.067(6) 0.056(6) -0.028(5) -0.016(4) -0.015(5) C10_1 0.056(5) 0.045(5) 0.047(5) -0.014(4) -0.004(4) -0.009(4) C11_1 0.094(7) 0.035(4) 0.034(5) 0.001(4) -0.020(5) -0.024(5) C12_1 0.040(5) 0.073(6) 0.052(5) -0.004(4) -0.014(4) -0.026(5) C13_1 0.049(5) 0.057(5) 0.040(5) -0.008(4) -0.010(4) -0.018(4) C14_1 0.066(6) 0.056(5) 0.031(4) -0.013(4) 0.003(4) -0.030(5) Br1_2 0.0678(6) 0.1211(9) 0.0322(5) 0.0190(5) -0.0227(4) -0.0504(6) Br2_2 0.0593(5) 0.0673(6) 0.0405(5) -0.0233(4) -0.0073(4) -0.0295(5) S1_2 0.0442(12) 0.0545(13) 0.0378(11) 0.0107(9) -0.0132(9) -0.0240(10) S2_2 0.0488(12) 0.0414(11) 0.0386(11) -0.0098(9) -0.0038(9) -0.0232(10) S3_2 0.0435(11) 0.0379(10) 0.0260(10) -0.0039(8) -0.0094(8) -0.0182(9) Si1_2 0.0458(13) 0.0664(16) 0.0332(12) -0.0157(11) -0.0193(10) -0.0054(12) Si2_2 0.0423(12) 0.0432(12) 0.0274(11) -0.0037(9) -0.0081(9) -0.0174(10) C1_2 0.042(5) 0.069(6) 0.026(4) 0.015(4) -0.022(4) -0.024(4) C2_2 0.035(4) 0.051(5) 0.028(4) -0.002(3) -0.014(3) -0.009(4) C3_2 0.029(4) 0.042(4) 0.030(4) 0.001(3) -0.011(3) -0.011(3) C4_2 0.029(4) 0.033(4) 0.031(4) 0.001(3) -0.009(3) -0.004(3) C5_2 0.037(4) 0.051(5) 0.021(4) -0.009(3) -0.003(3) -0.016(4) C6_2 0.036(4) 0.037(4) 0.032(4) -0.005(3) -0.001(3) -0.018(4) C7_2 0.035(4) 0.032(4) 0.024(4) -0.004(3) -0.009(3) -0.011(3) C8_2 0.030(4) 0.030(4) 0.038(4) -0.007(3) -0.009(3) -0.005(3) C9_2 0.052(5) 0.073(6) 0.042(5) -0.016(4) -0.018(4) -0.015(5) C10_2 0.060(6) 0.137(10) 0.072(7) -0.050(7) -0.034(6) 0.018(7) C11_2 0.117(9) 0.059(6) 0.062(6) -0.006(5) -0.056(6) -0.032(6) C12_2 0.067(6) 0.065(6) 0.039(5) -0.007(4) 0.000(4) -0.029(5) C13_2 0.061(6) 0.053(5) 0.069(6) 0.002(5) -0.031(5) -0.019(5) C14_2 0.077(6) 0.045(5) 0.041(5) 0.002(4) -0.016(4) -0.033(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Br1_1 C1_1 1.882(6) . ? Br2_1 C5_1 1.878(6) . ? S1_1 C4_1 1.725(6) . ? S1_1 C1_1 1.733(7) . ? S2_1 C8_1 1.721(6) . ? S2_1 C5_1 1.749(7) . ? S3_1 C3_1 1.743(6) . ? S3_1 C7_1 1.743(7) . ? Si1_1 C11_1 1.848(7) . ? Si1_1 C10_1 1.871(9) . ? Si1_1 C9_1 1.872(8) . ? Si1_1 C2_1 1.875(7) . ? Si2_1 C13_1 1.853(8) . ? Si2_1 C14_1 1.857(7) . ? Si2_1 C12_1 1.864(7) . ? Si2_1 C6_1 1.889(6) . ? C1_1 C2_1 1.372(9) . ? C2_1 C3_1 1.444(8) . ? C3_1 C4_1 1.386(9) . ? C4_1 C8_1 1.415(9) . ? C5_1 C6_1 1.353(9) . ? C6_1 C7_1 1.440(9) . ? C7_1 C8_1 1.385(9) . ? C9_1 H9A_1 0.9800 . ? C9_1 H9B_1 0.9800 . ? C9_1 H9C_1 0.9800 . ? C10_1 H10A_1 0.9800 . ? C10_1 H10B_1 0.9800 . ? C10_1 H10C_1 0.9800 . ? C11_1 H11A_1 0.9800 . ? C11_1 H11B_1 0.9800 . ? C11_1 H11C_1 0.9800 . ? C12_1 H12A_1 0.9800 . ? C12_1 H12B_1 0.9800 . ? C12_1 H12C_1 0.9800 . ? C13_1 H13A_1 0.9800 . ? C13_1 H13B_1 0.9800 . ? C13_1 H13C_1 0.9800 . ? C14_1 H14A_1 0.9800 . ? C14_1 H14B_1 0.9800 . ? C14_1 H14C_1 0.9800 . ? Br1_2 C1_2 1.881(7) . ? Br2_2 C5_2 1.871(7) . ? S1_2 C4_2 1.723(7) . ? S1_2 C1_2 1.730(8) . ? S2_2 C8_2 1.722(7) . ? S2_2 C5_2 1.734(7) . ? S3_2 C7_2 1.727(7) . ? S3_2 C3_2 1.748(7) . ? Si1_2 C11_2 1.854(9) . ? Si1_2 C10_2 1.855(10) . ? Si1_2 C9_2 1.874(9) . ? Si1_2 C2_2 1.889(8) . ? Si2_2 C12_2 1.831(8) . ? Si2_2 C14_2 1.851(7) . ? Si2_2 C13_2 1.858(9) . ? Si2_2 C6_2 1.882(7) . ? C1_2 C2_2 1.379(10) . ? C2_2 C3_2 1.440(10) . ? C3_2 C4_2 1.381(10) . ? C4_2 C8_2 1.414(10) . ? C5_2 C6_2 1.384(9) . ? C6_2 C7_2 1.455(10) . ? C7_2 C8_2 1.384(9) . ? C9_2 H9A_2 0.9800 . ? C9_2 H9B_2 0.9800 . ? C9_2 H9C_2 0.9800 . ? C10_2 H10A_2 0.9800 . ? C10_2 H10B_2 0.9800 . ? C10_2 H10C_2 0.9800 . ? C11_2 H11A_2 0.9800 . ? C11_2 H11B_2 0.9800 . ? C11_2 H11C_2 0.9800 . ? C12_2 H12A_2 0.9800 . ? C12_2 H12B_2 0.9800 . ? C12_2 H12C_2 0.9800 . ? C13_2 H13A_2 0.9800 . ? C13_2 H13B_2 0.9800 . ? C13_2 H13C_2 0.9800 . ? C14_2 H14A_2 0.9800 . ? C14_2 H14B_2 0.9800 . ? C14_2 H14C_2 0.9800 . ? 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_1 S1_1 C1_1 89.7(3) . . ? C8_1 S2_1 C5_1 89.6(3) . . ? C3_1 S3_1 C7_1 91.3(3) . . ? C11_1 Si1_1 C10_1 107.2(4) . . ? C11_1 Si1_1 C9_1 108.5(4) . . ? C10_1 Si1_1 C9_1 113.8(4) . . ? C11_1 Si1_1 C2_1 110.2(3) . . ? C10_1 Si1_1 C2_1 107.2(4) . . ? C9_1 Si1_1 C2_1 109.8(3) . . ? C13_1 Si2_1 C14_1 107.0(4) . . ? C13_1 Si2_1 C12_1 110.2(4) . . ? C14_1 Si2_1 C12_1 110.9(4) . . ? C13_1 Si2_1 C6_1 110.8(3) . . ? C14_1 Si2_1 C6_1 109.4(3) . . ? C12_1 Si2_1 C6_1 108.5(3) . . ? C2_1 C1_1 S1_1 116.9(5) . . ? C2_1 C1_1 Br1_1 126.5(5) . . ? S1_1 C1_1 Br1_1 116.6(3) . . ? C1_1 C2_1 C3_1 106.5(6) . . ? C1_1 C2_1 Si1_1 126.8(5) . . ? C3_1 C2_1 Si1_1 126.6(5) . . ? C4_1 C3_1 C2_1 115.9(5) . . ? C4_1 C3_1 S3_1 111.3(4) . . ? C2_1 C3_1 S3_1 132.8(5) . . ? C3_1 C4_1 C8_1 113.0(5) . . ? C3_1 C4_1 S1_1 111.0(5) . . ? C8_1 C4_1 S1_1 136.0(5) . . ? C6_1 C5_1 S2_1 116.3(5) . . ? C6_1 C5_1 Br2_1 128.0(5) . . ? S2_1 C5_1 Br2_1 115.7(4) . . ? C5_1 C6_1 C7_1 107.4(5) . . ? C5_1 C6_1 Si2_1 125.4(5) . . ? C7_1 C6_1 Si2_1 127.2(5) . . ? C8_1 C7_1 C6_1 115.6(6) . . ? C8_1 C7_1 S3_1 111.5(5) . . ? C6_1 C7_1 S3_1 132.9(5) . . ? C7_1 C8_1 C4_1 112.8(6) . . ? C7_1 C8_1 S2_1 111.1(5) . . ? C4_1 C8_1 S2_1 136.1(5) . . ? Si1_1 C9_1 H9A_1 109.5 . . ? Si1_1 C9_1 H9B_1 109.5 . . ? H9A_1 C9_1 H9B_1 109.5 . . ? Si1_1 C9_1 H9C_1 109.5 . . ? H9A_1 C9_1 H9C_1 109.5 . . ? H9B_1 C9_1 H9C_1 109.5 . . ? Si1_1 C10_1 H10A_1 109.5 . . ? Si1_1 C10_1 H10B_1 109.5 . . ? H10A_1 C10_1 H10B_1 109.5 . . ? Si1_1 C10_1 H10C_1 109.5 . . ? H10A_1 C10_1 H10C_1 109.5 . . ? H10B_1 C10_1 H10C_1 109.5 . . ? Si1_1 C11_1 H11A_1 109.5 . . ? Si1_1 C11_1 H11B_1 109.5 . . ? H11A_1 C11_1 H11B_1 109.5 . . ? Si1_1 C11_1 H11C_1 109.5 . . ? H11A_1 C11_1 H11C_1 109.5 . . ? H11B_1 C11_1 H11C_1 109.5 . . ? Si2_1 C12_1 H12A_1 109.5 . . ? Si2_1 C12_1 H12B_1 109.5 . . ? H12A_1 C12_1 H12B_1 109.5 . . ? Si2_1 C12_1 H12C_1 109.5 . . ? H12A_1 C12_1 H12C_1 109.5 . . ? H12B_1 C12_1 H12C_1 109.5 . . ? Si2_1 C13_1 H13A_1 109.5 . . ? Si2_1 C13_1 H13B_1 109.5 . . ? H13A_1 C13_1 H13B_1 109.5 . . ? Si2_1 C13_1 H13C_1 109.5 . . ? H13A_1 C13_1 H13C_1 109.5 . . ? H13B_1 C13_1 H13C_1 109.5 . . ? Si2_1 C14_1 H14A_1 109.5 . . ? Si2_1 C14_1 H14B_1 109.5 . . ? H14A_1 C14_1 H14B_1 109.5 . . ? Si2_1 C14_1 H14C_1 109.5 . . ? H14A_1 C14_1 H14C_1 109.5 . . ? H14B_1 C14_1 H14C_1 109.5 . . ? C4_2 S1_2 C1_2 89.9(3) . . ? C8_2 S2_2 C5_2 90.6(3) . . ? C7_2 S3_2 C3_2 90.7(3) . . ? C11_2 Si1_2 C10_2 109.5(5) . . ? C11_2 Si1_2 C9_2 110.7(4) . . ? C10_2 Si1_2 C9_2 109.8(4) . . ? C11_2 Si1_2 C2_2 108.4(3) . . ? C10_2 Si1_2 C2_2 110.5(4) . . ? C9_2 Si1_2 C2_2 107.9(4) . . ? C12_2 Si2_2 C14_2 108.0(4) . . ? C12_2 Si2_2 C13_2 111.4(4) . . ? C14_2 Si2_2 C13_2 109.7(4) . . ? C12_2 Si2_2 C6_2 109.3(4) . . ? C14_2 Si2_2 C6_2 109.5(3) . . ? C13_2 Si2_2 C6_2 108.9(3) . . ? C2_2 C1_2 S1_2 116.7(5) . . ? C2_2 C1_2 Br1_2 126.9(6) . . ? S1_2 C1_2 Br1_2 116.4(4) . . ? C1_2 C2_2 C3_2 106.3(6) . . ? C1_2 C2_2 Si1_2 125.7(5) . . ? C3_2 C2_2 Si1_2 127.9(5) . . ? C4_2 C3_2 C2_2 116.3(6) . . ? C4_2 C3_2 S3_2 111.5(5) . . ? C2_2 C3_2 S3_2 132.2(5) . . ? C3_2 C4_2 C8_2 113.0(6) . . ? C3_2 C4_2 S1_2 110.9(5) . . ? C8_2 C4_2 S1_2 136.0(5) . . ? C6_2 C5_2 S2_2 115.5(5) . . ? C6_2 C5_2 Br2_2 127.3(5) . . ? S2_2 C5_2 Br2_2 117.3(4) . . ? C5_2 C6_2 C7_2 107.5(6) . . ? C5_2 C6_2 Si2_2 124.9(6) . . ? C7_2 C6_2 Si2_2 127.6(5) . . ? C8_2 C7_2 C6_2 115.0(6) . . ? C8_2 C7_2 S3_2 112.7(5) . . ? C6_2 C7_2 S3_2 132.3(5) . . ? C7_2 C8_2 C4_2 112.0(6) . . ? C7_2 C8_2 S2_2 111.4(5) . . ? C4_2 C8_2 S2_2 136.5(5) . . ? Si1_2 C9_2 H9A_2 109.5 . . ? Si1_2 C9_2 H9B_2 109.5 . . ? H9A_2 C9_2 H9B_2 109.5 . . ? Si1_2 C9_2 H9C_2 109.5 . . ? H9A_2 C9_2 H9C_2 109.5 . . ? H9B_2 C9_2 H9C_2 109.5 . . ? Si1_2 C10_2 H10A_2 109.5 . . ? Si1_2 C10_2 H10B_2 109.5 . . ? H10A_2 C10_2 H10B_2 109.5 . . ? Si1_2 C10_2 H10C_2 109.5 . . ? H10A_2 C10_2 H10C_2 109.5 . . ? H10B_2 C10_2 H10C_2 109.5 . . ? Si1_2 C11_2 H11A_2 109.5 . . ? Si1_2 C11_2 H11B_2 109.5 . . ? H11A_2 C11_2 H11B_2 109.5 . . ? Si1_2 C11_2 H11C_2 109.5 . . ? H11A_2 C11_2 H11C_2 109.5 . . ? H11B_2 C11_2 H11C_2 109.5 . . ? Si2_2 C12_2 H12A_2 109.5 . . ? Si2_2 C12_2 H12B_2 109.5 . . ? H12A_2 C12_2 H12B_2 109.5 . . ? Si2_2 C12_2 H12C_2 109.5 . . ? H12A_2 C12_2 H12C_2 109.5 . . ? H12B_2 C12_2 H12C_2 109.5 . . ? Si2_2 C13_2 H13A_2 109.5 . . ? Si2_2 C13_2 H13B_2 109.5 . . ? H13A_2 C13_2 H13B_2 109.5 . . ? Si2_2 C13_2 H13C_2 109.5 . . ? H13A_2 C13_2 H13C_2 109.5 . . ? H13B_2 C13_2 H13C_2 109.5 . . ? Si2_2 C14_2 H14A_2 109.5 . . ? Si2_2 C14_2 H14B_2 109.5 . . ? H14A_2 C14_2 H14B_2 109.5 . . ? Si2_2 C14_2 H14C_2 109.5 . . ? H14A_2 C14_2 H14C_2 109.5 . . ? H14B_2 C14_2 H14C_2 109.5 . . ? 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 C4_1 S1_1 C1_1 C2_1 0.6(6) . . . . ? C4_1 S1_1 C1_1 Br1_1 178.0(4) . . . . ? S1_1 C1_1 C2_1 C3_1 -1.8(8) . . . . ? Br1_1 C1_1 C2_1 C3_1 -178.8(5) . . . . ? S1_1 C1_1 C2_1 Si1_1 -179.5(4) . . . . ? Br1_1 C1_1 C2_1 Si1_1 3.4(10) . . . . ? C11_1 Si1_1 C2_1 C1_1 -169.3(7) . . . . ? C10_1 Si1_1 C2_1 C1_1 74.3(7) . . . . ? C9_1 Si1_1 C2_1 C1_1 -49.8(8) . . . . ? C11_1 Si1_1 C2_1 C3_1 13.4(8) . . . . ? C10_1 Si1_1 C2_1 C3_1 -103.0(7) . . . . ? C9_1 Si1_1 C2_1 C3_1 132.9(7) . . . . ? C1_1 C2_1 C3_1 C4_1 2.4(9) . . . . ? Si1_1 C2_1 C3_1 C4_1 -179.8(5) . . . . ? C1_1 C2_1 C3_1 S3_1 -179.9(6) . . . . ? Si1_1 C2_1 C3_1 S3_1 -2.1(11) . . . . ? C7_1 S3_1 C3_1 C4_1 1.3(6) . . . . ? C7_1 S3_1 C3_1 C2_1 -176.5(8) . . . . ? C2_1 C3_1 C4_1 C8_1 178.2(6) . . . . ? S3_1 C3_1 C4_1 C8_1 -0.1(8) . . . . ? C2_1 C3_1 C4_1 S1_1 -2.0(8) . . . . ? S3_1 C3_1 C4_1 S1_1 179.7(4) . . . . ? C1_1 S1_1 C4_1 C3_1 0.8(6) . . . . ? C1_1 S1_1 C4_1 C8_1 -179.5(8) . . . . ? C8_1 S2_1 C5_1 C6_1 1.0(6) . . . . ? C8_1 S2_1 C5_1 Br2_1 -177.1(4) . . . . ? S2_1 C5_1 C6_1 C7_1 -0.3(8) . . . . ? Br2_1 C5_1 C6_1 C7_1 177.6(5) . . . . ? S2_1 C5_1 C6_1 Si2_1 179.0(4) . . . . ? Br2_1 C5_1 C6_1 Si2_1 -3.1(10) . . . . ? C13_1 Si2_1 C6_1 C5_1 57.0(7) . . . . ? C14_1 Si2_1 C6_1 C5_1 174.7(6) . . . . ? C12_1 Si2_1 C6_1 C5_1 -64.2(7) . . . . ? C13_1 Si2_1 C6_1 C7_1 -123.9(6) . . . . ? C14_1 Si2_1 C6_1 C7_1 -6.1(8) . . . . ? C12_1 Si2_1 C6_1 C7_1 115.0(7) . . . . ? C5_1 C6_1 C7_1 C8_1 -0.9(9) . . . . ? Si2_1 C6_1 C7_1 C8_1 179.8(5) . . . . ? C5_1 C6_1 C7_1 S3_1 179.8(6) . . . . ? Si2_1 C6_1 C7_1 S3_1 0.6(11) . . . . ? C3_1 S3_1 C7_1 C8_1 -2.3(6) . . . . ? C3_1 S3_1 C7_1 C6_1 177.0(7) . . . . ? C6_1 C7_1 C8_1 C4_1 -176.7(6) . . . . ? S3_1 C7_1 C8_1 C4_1 2.7(8) . . . . ? C6_1 C7_1 C8_1 S2_1 1.7(8) . . . . ? S3_1 C7_1 C8_1 S2_1 -178.9(4) . . . . ? C3_1 C4_1 C8_1 C7_1 -1.7(9) . . . . ? S1_1 C4_1 C8_1 C7_1 178.6(6) . . . . ? C3_1 C4_1 C8_1 S2_1 -179.6(6) . . . . ? S1_1 C4_1 C8_1 S2_1 0.7(13) . . . . ? C5_1 S2_1 C8_1 C7_1 -1.5(6) . . . . ? C5_1 S2_1 C8_1 C4_1 176.5(8) . . . . ? C4_2 S1_2 C1_2 C2_2 0.1(6) . . . . ? C4_2 S1_2 C1_2 Br1_2 178.8(5) . . . . ? S1_2 C1_2 C2_2 C3_2 -0.3(8) . . . . ? Br1_2 C1_2 C2_2 C3_2 -178.8(6) . . . . ? S1_2 C1_2 C2_2 Si1_2 177.6(4) . . . . ? Br1_2 C1_2 C2_2 Si1_2 -0.9(10) . . . . ? C11_2 Si1_2 C2_2 C1_2 173.8(7) . . . . ? C10_2 Si1_2 C2_2 C1_2 53.8(8) . . . . ? C9_2 Si1_2 C2_2 C1_2 -66.3(7) . . . . ? C11_2 Si1_2 C2_2 C3_2 -8.8(8) . . . . ? C10_2 Si1_2 C2_2 C3_2 -128.8(7) . . . . ? C9_2 Si1_2 C2_2 C3_2 111.1(7) . . . . ? C1_2 C2_2 C3_2 C4_2 0.4(9) . . . . ? Si1_2 C2_2 C3_2 C4_2 -177.4(5) . . . . ? C1_2 C2_2 C3_2 S3_2 -179.2(6) . . . . ? Si1_2 C2_2 C3_2 S3_2 3.0(11) . . . . ? C7_2 S3_2 C3_2 C4_2 -1.8(6) . . . . ? C7_2 S3_2 C3_2 C2_2 177.8(8) . . . . ? C2_2 C3_2 C4_2 C8_2 -177.6(6) . . . . ? S3_2 C3_2 C4_2 C8_2 2.0(8) . . . . ? C2_2 C3_2 C4_2 S1_2 -0.3(9) . . . . ? S3_2 C3_2 C4_2 S1_2 179.4(4) . . . . ? C1_2 S1_2 C4_2 C3_2 0.1(6) . . . . ? C1_2 S1_2 C4_2 C8_2 176.5(8) . . . . ? C8_2 S2_2 C5_2 C6_2 -1.0(6) . . . . ? C8_2 S2_2 C5_2 Br2_2 178.8(4) . . . . ? S2_2 C5_2 C6_2 C7_2 0.4(8) . . . . ? Br2_2 C5_2 C6_2 C7_2 -179.3(5) . . . . ? S2_2 C5_2 C6_2 Si2_2 178.1(4) . . . . ? Br2_2 C5_2 C6_2 Si2_2 -1.6(10) . . . . ? C12_2 Si2_2 C6_2 C5_2 60.2(8) . . . . ? C14_2 Si2_2 C6_2 C5_2 178.3(7) . . . . ? C13_2 Si2_2 C6_2 C5_2 -61.7(8) . . . . ? C12_2 Si2_2 C6_2 C7_2 -122.6(7) . . . . ? C14_2 Si2_2 C6_2 C7_2 -4.5(8) . . . . ? C13_2 Si2_2 C6_2 C7_2 115.5(7) . . . . ? C5_2 C6_2 C7_2 C8_2 0.6(9) . . . . ? Si2_2 C6_2 C7_2 C8_2 -177.0(5) . . . . ? C5_2 C6_2 C7_2 S3_2 176.7(6) . . . . ? Si2_2 C6_2 C7_2 S3_2 -0.9(11) . . . . ? C3_2 S3_2 C7_2 C8_2 1.1(6) . . . . ? C3_2 S3_2 C7_2 C6_2 -175.1(7) . . . . ? C6_2 C7_2 C8_2 C4_2 176.8(6) . . . . ? S3_2 C7_2 C8_2 C4_2 -0.1(8) . . . . ? C6_2 C7_2 C8_2 S2_2 -1.4(8) . . . . ? S3_2 C7_2 C8_2 S2_2 -178.3(4) . . . . ? C3_2 C4_2 C8_2 C7_2 -1.3(9) . . . . ? S1_2 C4_2 C8_2 C7_2 -177.7(6) . . . . ? C3_2 C4_2 C8_2 S2_2 176.3(6) . . . . ? S1_2 C4_2 C8_2 S2_2 -0.2(13) . . . . ? C5_2 S2_2 C8_2 C7_2 1.3(6) . . . . ? C5_2 S2_2 C8_2 C4_2 -176.2(8) . . . . ? #===END ######################## ## denoted 12 in text ## ######################## data_ah0131 _database_code_CSD 190975 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C28 H32 S5' _chemical_formula_sum 'C28 H32 S5' _chemical_formula_weight 528.84 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 triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.8796(4) _cell_length_b 11.3296(5) _cell_length_c 15.8922(8) _cell_angle_alpha 76.087(3) _cell_angle_beta 83.466(3) _cell_angle_gamma 71.136(3) _cell_volume 1302.15(11) _cell_formula_units_Z 2 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 15629 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 27.48 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.349 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 560 _exptl_absorpt_coefficient_mu 0.461 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.889 _exptl_absorpt_correction_T_max 0.927 _exptl_absorpt_process_details 'Sortav Blessing (1995)' _exptl_special_details ; Residual electron density towards the end of the C23-C28 hexyl chain suggests slight disorder. Modelling in two orientations leaves one refining to ca. 10% occupancy - this was deemed insignificant and disorder was not therefore modelled. ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.7107 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method 'Thin slice \w and \f scans' _diffrn_standards_number 0 _diffrn_reflns_number 14683 _diffrn_reflns_av_R_equivalents 0.0371 _diffrn_reflns_av_sigmaI/netI 0.0511 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 3.61 _diffrn_reflns_theta_max 27.52 _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 27.52 _diffrn_measured_fraction_theta_full 0.990 _reflns_number_total 5930 _reflns_number_gt 4605 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V. 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction ; HKL Denzo and Scalepack (Otwinowski & Minor 1997) ; _computing_structure_solution 'SIR-92 (Altomare et al. 1994)' _computing_structure_refinement 'SHELXTL v6.12 (Bruker AXS, 2001)' _computing_publication_material 'SHELXTL v6.12 (Bruker AXS, 2001)' _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^)+(0.0461P)^2^+1.0633P] 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 5930 _refine_ls_number_parameters 300 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0670 _refine_ls_R_factor_gt 0.0482 _refine_ls_wR_factor_ref 0.1192 _refine_ls_wR_factor_gt 0.1096 _refine_ls_goodness_of_fit_ref 1.023 _refine_ls_restrained_S_all 1.023 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 1.065 _refine_diff_density_min -0.466 _refine_diff_density_rms 0.064 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 -0.77289(9) -0.03462(6) 0.58300(4) 0.03629(16) Uani 1 1 d . . . S2 S -0.43449(8) -0.03109(6) 0.78388(4) 0.03144(15) Uani 1 1 d . . . S3 S -0.21950(8) 0.21043(6) 0.59215(4) 0.03468(16) Uani 1 1 d . . . S4 S -0.07301(8) 0.09520(6) 0.85091(4) 0.03179(15) Uani 1 1 d . . . S5 S 0.22844(9) 0.12795(6) 0.94935(4) 0.03944(17) Uani 1 1 d . . . C1 C -0.9112(3) -0.1254(2) 0.62462(17) 0.0370(6) Uani 1 1 d . . . H1A H -0.9959 -0.1369 0.5919 0.044 Uiso 1 1 calc R . . C2 C -0.8855(3) -0.1788(2) 0.70994(17) 0.0355(5) Uani 1 1 d . . . H2A H -0.9511 -0.2322 0.7435 0.043 Uiso 1 1 calc R . . C3 C -0.7504(3) -0.1473(2) 0.74461(15) 0.0292(5) Uani 1 1 d . . . C4 C -0.6767(3) -0.0682(2) 0.68255(15) 0.0288(5) Uani 1 1 d . . . C5 C -0.5386(3) -0.0100(2) 0.68733(15) 0.0284(5) Uani 1 1 d . . . C6 C -0.4769(3) 0.0689(2) 0.62000(15) 0.0304(5) Uani 1 1 d . . . H6A H -0.5175 0.0917 0.5625 0.036 Uiso 1 1 calc R . . C7 C -0.3459(3) 0.1124(2) 0.64588(15) 0.0292(5) Uani 1 1 d . . . C8 C -0.3096(3) 0.0670(2) 0.73329(15) 0.0278(5) Uani 1 1 d . . . C9 C -0.1773(3) 0.1120(2) 0.75742(14) 0.0278(5) Uani 1 1 d . . . C10 C -0.1154(3) 0.1896(2) 0.68834(15) 0.0292(5) Uani 1 1 d . . . C11 C 0.0189(3) 0.2343(2) 0.70942(15) 0.0308(5) Uani 1 1 d . . . H11A H 0.0754 0.2879 0.6689 0.037 Uiso 1 1 calc R . . C12 C 0.0579(3) 0.1911(2) 0.79549(15) 0.0290(5) Uani 1 1 d . . . C13 C 0.1890(3) 0.2125(2) 0.84332(15) 0.0299(5) Uani 1 1 d . . . C14 C 0.2982(3) 0.2894(2) 0.81649(16) 0.0317(5) Uani 1 1 d . . . C15 C 0.4117(4) 0.2782(3) 0.88289(17) 0.0403(6) Uani 1 1 d . . . H15A H 0.4957 0.3244 0.8757 0.048 Uiso 1 1 calc R . . C16 C 0.3897(4) 0.1952(3) 0.95797(18) 0.0463(7) Uani 1 1 d . . . H16A H 0.4553 0.1770 1.0086 0.056 Uiso 1 1 calc R . . C17 C -0.6951(3) -0.1970(2) 0.83759(15) 0.0318(5) Uani 1 1 d . . . H17A H -0.7176 -0.1233 0.8650 0.038 Uiso 1 1 calc R . . H17B H -0.5644 -0.2416 0.8380 0.038 Uiso 1 1 calc R . . C18 C -0.7917(3) -0.2880(2) 0.89232(15) 0.0338(5) Uani 1 1 d . . . H18A H -0.9224 -0.2433 0.8929 0.041 Uiso 1 1 calc R . . H18B H -0.7703 -0.3616 0.8649 0.041 Uiso 1 1 calc R . . C19 C -0.7316(3) -0.3373(2) 0.98513(15) 0.0332(5) Uani 1 1 d . . . H19A H -0.7637 -0.2647 1.0144 0.040 Uiso 1 1 calc R . . H19B H -0.5993 -0.3749 0.9846 0.040 Uiso 1 1 calc R . . C20 C -0.8160(3) -0.4374(2) 1.03656(16) 0.0354(5) Uani 1 1 d . . . H20A H -0.9481 -0.3993 1.0370 0.043 Uiso 1 1 calc R . . H20B H -0.7847 -0.5092 1.0066 0.043 Uiso 1 1 calc R . . C21 C -0.7579(4) -0.4898(2) 1.12960(16) 0.0368(6) Uani 1 1 d . . . H21A H -0.7928 -0.4191 1.1607 0.044 Uiso 1 1 calc R . . H21B H -0.6255 -0.5265 1.1298 0.044 Uiso 1 1 calc R . . C22 C -0.8423(4) -0.5922(3) 1.17700(19) 0.0505(7) Uani 1 1 d . . . H22A H -0.7954 -0.6277 1.2353 0.076 Uiso 1 1 calc R . . H22B H -0.8128 -0.6605 1.1448 0.076 Uiso 1 1 calc R . . H22C H -0.9729 -0.5544 1.1813 0.076 Uiso 1 1 calc R . . C23 C 0.3027(3) 0.3728(2) 0.72692(16) 0.0323(5) Uani 1 1 d . . . H23A H 0.1795 0.4304 0.7142 0.039 Uiso 1 1 calc R . . H23B H 0.3376 0.3172 0.6844 0.039 Uiso 1 1 calc R . . C24 C 0.4284(3) 0.4541(2) 0.71268(17) 0.0376(6) Uani 1 1 d . . . H24A H 0.5526 0.3977 0.7243 0.045 Uiso 1 1 calc R . . H24B H 0.3940 0.5112 0.7542 0.045 Uiso 1 1 calc R . . C25 C 0.4226(4) 0.5346(3) 0.62029(18) 0.0439(6) Uani 1 1 d . . . H25A H 0.4587 0.4759 0.5798 0.053 Uiso 1 1 calc R . . H25B H 0.2965 0.5872 0.6090 0.053 Uiso 1 1 calc R . . C26 C 0.5386(4) 0.6232(3) 0.5985(2) 0.0537(8) Uani 1 1 d . . . H26A H 0.5020 0.6827 0.5422 0.064 Uiso 1 1 calc R . . H26B H 0.5134 0.6750 0.6431 0.064 Uiso 1 1 calc R . . C27 C 0.7336(4) 0.5599(3) 0.5929(2) 0.0575(8) Uani 1 1 d . . . H27A H 0.7596 0.5015 0.5524 0.069 Uiso 1 1 calc R . . H27B H 0.7745 0.5079 0.6508 0.069 Uiso 1 1 calc R . . C28 C 0.8395(5) 0.6578(4) 0.5612(2) 0.0705(10) Uani 1 1 d . . . H28A H 0.8091 0.7030 0.5014 0.106 Uiso 1 1 calc R . . H28B H 0.9686 0.6127 0.5634 0.106 Uiso 1 1 calc R . . H28C H 0.8075 0.7195 0.5987 0.106 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 0.0388(3) 0.0436(3) 0.0298(3) -0.0050(3) -0.0069(3) -0.0173(3) S2 0.0343(3) 0.0352(3) 0.0270(3) -0.0025(2) -0.0034(2) -0.0159(2) S3 0.0367(3) 0.0427(3) 0.0273(3) -0.0001(2) -0.0058(2) -0.0195(3) S4 0.0346(3) 0.0368(3) 0.0261(3) -0.0043(2) -0.0029(2) -0.0151(2) S5 0.0436(4) 0.0451(4) 0.0301(3) -0.0016(3) -0.0084(3) -0.0167(3) C1 0.0368(13) 0.0437(14) 0.0367(14) -0.0093(11) -0.0063(11) -0.0186(11) C2 0.0352(13) 0.0383(13) 0.0372(14) -0.0091(11) -0.0012(10) -0.0164(11) C3 0.0282(11) 0.0294(11) 0.0304(12) -0.0080(9) -0.0001(9) -0.0086(9) C4 0.0267(11) 0.0307(11) 0.0286(12) -0.0071(9) -0.0046(9) -0.0065(9) C5 0.0278(11) 0.0295(11) 0.0273(12) -0.0064(9) -0.0021(9) -0.0073(9) C6 0.0302(12) 0.0341(12) 0.0276(12) -0.0046(9) -0.0058(9) -0.0109(10) C7 0.0287(12) 0.0302(11) 0.0275(12) -0.0027(9) -0.0021(9) -0.0093(9) C8 0.0269(11) 0.0278(11) 0.0280(12) -0.0049(9) -0.0016(9) -0.0084(9) C9 0.0278(11) 0.0283(11) 0.0266(12) -0.0057(9) -0.0018(9) -0.0078(9) C10 0.0299(12) 0.0312(11) 0.0265(12) -0.0041(9) -0.0018(9) -0.0105(9) C11 0.0287(12) 0.0335(12) 0.0314(12) -0.0049(10) -0.0041(10) -0.0115(10) C12 0.0258(11) 0.0294(11) 0.0308(12) -0.0067(9) -0.0012(9) -0.0069(9) C13 0.0293(12) 0.0333(12) 0.0265(12) -0.0060(9) -0.0028(9) -0.0086(9) C14 0.0302(12) 0.0344(12) 0.0327(13) -0.0115(10) -0.0035(10) -0.0092(10) C15 0.0412(14) 0.0439(14) 0.0404(15) -0.0083(12) -0.0090(12) -0.0173(12) C16 0.0470(16) 0.0556(17) 0.0398(15) -0.0083(13) -0.0169(13) -0.0166(13) C17 0.0306(12) 0.0330(12) 0.0329(13) -0.0050(10) -0.0038(10) -0.0119(10) C18 0.0372(13) 0.0375(13) 0.0308(13) -0.0075(10) -0.0009(10) -0.0172(11) C19 0.0364(13) 0.0361(12) 0.0300(12) -0.0080(10) -0.0004(10) -0.0147(10) C20 0.0384(13) 0.0348(13) 0.0355(14) -0.0074(10) -0.0008(11) -0.0149(11) C21 0.0453(15) 0.0340(12) 0.0320(13) -0.0048(10) -0.0006(11) -0.0152(11) C22 0.0636(19) 0.0496(16) 0.0401(16) -0.0018(13) 0.0006(14) -0.0265(14) C23 0.0294(12) 0.0360(12) 0.0336(13) -0.0083(10) -0.0030(10) -0.0118(10) C24 0.0340(13) 0.0408(13) 0.0437(15) -0.0149(12) 0.0005(11) -0.0157(11) C25 0.0479(16) 0.0448(15) 0.0436(16) -0.0086(12) 0.0079(13) -0.0244(13) C26 0.0572(19) 0.0492(16) 0.062(2) -0.0169(15) 0.0077(15) -0.0252(14) C27 0.0539(19) 0.0611(19) 0.065(2) -0.0159(16) 0.0000(16) -0.0271(16) C28 0.064(2) 0.096(3) 0.066(2) -0.007(2) 0.0049(18) -0.053(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 C1 1.707(3) . ? S1 C4 1.737(2) . ? S2 C8 1.717(2) . ? S2 C5 1.752(2) . ? S3 C7 1.738(2) . ? S3 C10 1.747(2) . ? S4 C9 1.720(2) . ? S4 C12 1.754(2) . ? S5 C16 1.711(3) . ? S5 C13 1.733(2) . ? C1 C2 1.354(4) . ? C1 H1A 0.9500 . ? C2 C3 1.428(3) . ? C2 H2A 0.9500 . ? C3 C4 1.376(3) . ? C3 C17 1.509(3) . ? C4 C5 1.460(3) . ? C5 C6 1.373(3) . ? C6 C7 1.414(3) . ? C6 H6A 0.9500 . ? C7 C8 1.388(3) . ? C8 C9 1.422(3) . ? C9 C10 1.381(3) . ? C10 C11 1.413(3) . ? C11 C12 1.372(3) . ? C11 H11A 0.9500 . ? C12 C13 1.461(3) . ? C13 C14 1.380(3) . ? C14 C15 1.416(3) . ? C14 C23 1.511(3) . ? C15 C16 1.363(4) . ? C15 H15A 0.9500 . ? C16 H16A 0.9500 . ? C17 C18 1.525(3) . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C18 C19 1.518(3) . ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? C19 C20 1.521(3) . ? C19 H19A 0.9900 . ? C19 H19B 0.9900 . ? C20 C21 1.518(3) . ? C20 H20A 0.9900 . ? C20 H20B 0.9900 . ? C21 C22 1.523(4) . ? C21 H21A 0.9900 . ? C21 H21B 0.9900 . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? C23 C24 1.523(3) . ? C23 H23A 0.9900 . ? C23 H23B 0.9900 . ? C24 C25 1.528(4) . ? C24 H24A 0.9900 . ? C24 H24B 0.9900 . ? C25 C26 1.522(4) . ? C25 H25A 0.9900 . ? C25 H25B 0.9900 . ? C26 C27 1.473(4) . ? C26 H26A 0.9900 . ? C26 H26B 0.9900 . ? C27 C28 1.554(4) . ? C27 H27A 0.9900 . ? C27 H27B 0.9900 . ? C28 H28A 0.9800 . ? C28 H28B 0.9800 . ? C28 H28C 0.9800 . ? 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 C4 91.87(12) . . ? C8 S2 C5 91.54(11) . . ? C7 S3 C10 90.36(11) . . ? C9 S4 C12 91.47(11) . . ? C16 S5 C13 92.03(13) . . ? C2 C1 S1 111.87(19) . . ? C2 C1 H1A 124.1 . . ? S1 C1 H1A 124.1 . . ? C1 C2 C3 113.6(2) . . ? C1 C2 H2A 123.2 . . ? C3 C2 H2A 123.2 . . ? C4 C3 C2 111.5(2) . . ? C4 C3 C17 124.9(2) . . ? C2 C3 C17 123.6(2) . . ? C3 C4 C5 131.4(2) . . ? C3 C4 S1 111.16(17) . . ? C5 C4 S1 117.42(17) . . ? C6 C5 C4 125.9(2) . . ? C6 C5 S2 111.48(17) . . ? C4 C5 S2 122.64(17) . . ? C5 C6 C7 112.3(2) . . ? C5 C6 H6A 123.8 . . ? C7 C6 H6A 123.8 . . ? C8 C7 C6 113.3(2) . . ? C8 C7 S3 112.63(17) . . ? C6 C7 S3 134.02(19) . . ? C7 C8 C9 112.1(2) . . ? C7 C8 S2 111.33(17) . . ? C9 C8 S2 136.56(18) . . ? C10 C9 C8 112.5(2) . . ? C10 C9 S4 110.95(17) . . ? C8 C9 S4 136.58(18) . . ? C9 C10 C11 114.1(2) . . ? C9 C10 S3 112.43(17) . . ? C11 C10 S3 133.42(18) . . ? C12 C11 C10 111.8(2) . . ? C12 C11 H11A 124.1 . . ? C10 C11 H11A 124.1 . . ? C11 C12 C13 129.6(2) . . ? C11 C12 S4 111.59(17) . . ? C13 C12 S4 118.85(17) . . ? C14 C13 C12 129.9(2) . . ? C14 C13 S5 111.16(18) . . ? C12 C13 S5 118.86(18) . . ? C13 C14 C15 111.6(2) . . ? C13 C14 C23 125.0(2) . . ? C15 C14 C23 123.3(2) . . ? C16 C15 C14 114.0(2) . . ? C16 C15 H15A 123.0 . . ? C14 C15 H15A 123.0 . . ? C15 C16 S5 111.2(2) . . ? C15 C16 H16A 124.4 . . ? S5 C16 H16A 124.4 . . ? C3 C17 C18 114.62(19) . . ? C3 C17 H17A 108.6 . . ? C18 C17 H17A 108.6 . . ? C3 C17 H17B 108.6 . . ? C18 C17 H17B 108.6 . . ? H17A C17 H17B 107.6 . . ? C19 C18 C17 113.26(19) . . ? C19 C18 H18A 108.9 . . ? C17 C18 H18A 108.9 . . ? C19 C18 H18B 108.9 . . ? C17 C18 H18B 108.9 . . ? H18A C18 H18B 107.7 . . ? C18 C19 C20 112.7(2) . . ? C18 C19 H19A 109.1 . . ? C20 C19 H19A 109.1 . . ? C18 C19 H19B 109.1 . . ? C20 C19 H19B 109.1 . . ? H19A C19 H19B 107.8 . . ? C21 C20 C19 114.2(2) . . ? C21 C20 H20A 108.7 . . ? C19 C20 H20A 108.7 . . ? C21 C20 H20B 108.7 . . ? C19 C20 H20B 108.7 . . ? H20A C20 H20B 107.6 . . ? C20 C21 C22 111.9(2) . . ? C20 C21 H21A 109.2 . . ? C22 C21 H21A 109.2 . . ? C20 C21 H21B 109.2 . . ? C22 C21 H21B 109.2 . . ? H21A C21 H21B 107.9 . . ? C21 C22 H22A 109.5 . . ? C21 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C21 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C14 C23 C24 116.1(2) . . ? C14 C23 H23A 108.3 . . ? C24 C23 H23A 108.3 . . ? C14 C23 H23B 108.3 . . ? C24 C23 H23B 108.3 . . ? H23A C23 H23B 107.4 . . ? C23 C24 C25 111.9(2) . . ? C23 C24 H24A 109.2 . . ? C25 C24 H24A 109.2 . . ? C23 C24 H24B 109.2 . . ? C25 C24 H24B 109.2 . . ? H24A C24 H24B 107.9 . . ? C26 C25 C24 117.0(2) . . ? C26 C25 H25A 108.0 . . ? C24 C25 H25A 108.0 . . ? C26 C25 H25B 108.0 . . ? C24 C25 H25B 108.0 . . ? H25A C25 H25B 107.3 . . ? C27 C26 C25 115.6(3) . . ? C27 C26 H26A 108.4 . . ? C25 C26 H26A 108.4 . . ? C27 C26 H26B 108.4 . . ? C25 C26 H26B 108.4 . . ? H26A C26 H26B 107.4 . . ? C26 C27 C28 111.9(3) . . ? C26 C27 H27A 109.2 . . ? C28 C27 H27A 109.2 . . ? C26 C27 H27B 109.2 . . ? C28 C27 H27B 109.2 . . ? H27A C27 H27B 107.9 . . ? C27 C28 H28A 109.5 . . ? C27 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? C27 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 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 C4 S1 C1 C2 -0.1(2) . . . . ? S1 C1 C2 C3 -0.1(3) . . . . ? C1 C2 C3 C4 0.2(3) . . . . ? C1 C2 C3 C17 -178.9(2) . . . . ? C2 C3 C4 C5 179.0(2) . . . . ? C17 C3 C4 C5 -1.9(4) . . . . ? C2 C3 C4 S1 -0.3(2) . . . . ? C17 C3 C4 S1 178.82(18) . . . . ? C1 S1 C4 C3 0.25(18) . . . . ? C1 S1 C4 C5 -179.16(18) . . . . ? C3 C4 C5 C6 -179.5(2) . . . . ? S1 C4 C5 C6 -0.2(3) . . . . ? C3 C4 C5 S2 -1.2(4) . . . . ? S1 C4 C5 S2 178.02(12) . . . . ? C8 S2 C5 C6 0.33(18) . . . . ? C8 S2 C5 C4 -178.16(19) . . . . ? C4 C5 C6 C7 178.5(2) . . . . ? S2 C5 C6 C7 0.0(2) . . . . ? C5 C6 C7 C8 -0.5(3) . . . . ? C5 C6 C7 S3 179.42(18) . . . . ? C10 S3 C7 C8 0.30(18) . . . . ? C10 S3 C7 C6 -179.6(2) . . . . ? C6 C7 C8 C9 179.90(19) . . . . ? S3 C7 C8 C9 -0.1(2) . . . . ? C6 C7 C8 S2 0.8(3) . . . . ? S3 C7 C8 S2 -179.19(11) . . . . ? C5 S2 C8 C7 -0.61(17) . . . . ? C5 S2 C8 C9 -179.5(2) . . . . ? C7 C8 C9 C10 -0.3(3) . . . . ? S2 C8 C9 C10 178.52(19) . . . . ? C7 C8 C9 S4 179.69(19) . . . . ? S2 C8 C9 S4 -1.5(4) . . . . ? C12 S4 C9 C10 -1.11(17) . . . . ? C12 S4 C9 C8 178.9(2) . . . . ? C8 C9 C10 C11 -178.84(19) . . . . ? S4 C9 C10 C11 1.2(3) . . . . ? C8 C9 C10 S3 0.5(2) . . . . ? S4 C9 C10 S3 -179.46(11) . . . . ? C7 S3 C10 C9 -0.48(18) . . . . ? C7 S3 C10 C11 178.7(2) . . . . ? C9 C10 C11 C12 -0.6(3) . . . . ? S3 C10 C11 C12 -179.76(19) . . . . ? C10 C11 C12 C13 178.8(2) . . . . ? C10 C11 C12 S4 -0.3(2) . . . . ? C9 S4 C12 C11 0.81(18) . . . . ? C9 S4 C12 C13 -178.40(18) . . . . ? C11 C12 C13 C14 5.6(4) . . . . ? S4 C12 C13 C14 -175.4(2) . . . . ? C11 C12 C13 S5 -171.7(2) . . . . ? S4 C12 C13 S5 7.4(3) . . . . ? C16 S5 C13 C14 0.14(19) . . . . ? C16 S5 C13 C12 177.87(19) . . . . ? C12 C13 C14 C15 -177.5(2) . . . . ? S5 C13 C14 C15 -0.1(3) . . . . ? C12 C13 C14 C23 0.7(4) . . . . ? S5 C13 C14 C23 178.08(18) . . . . ? C13 C14 C15 C16 0.1(3) . . . . ? C23 C14 C15 C16 -178.2(2) . . . . ? C14 C15 C16 S5 0.0(3) . . . . ? C13 S5 C16 C15 -0.1(2) . . . . ? C4 C3 C17 C18 -177.3(2) . . . . ? C2 C3 C17 C18 1.7(3) . . . . ? C3 C17 C18 C19 179.35(19) . . . . ? C17 C18 C19 C20 -174.6(2) . . . . ? C18 C19 C20 C21 179.6(2) . . . . ? C19 C20 C21 C22 -178.3(2) . . . . ? C13 C14 C23 C24 177.6(2) . . . . ? C15 C14 C23 C24 -4.4(3) . . . . ? C14 C23 C24 C25 -180.0(2) . . . . ? C23 C24 C25 C26 178.3(2) . . . . ? C24 C25 C26 C27 70.7(4) . . . . ? C25 C26 C27 C28 174.1(3) . . . . ? #===END