Supplementary Material (ESI) for Chemical Communications This journal is © The Royal Society of Chemistry 2004 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'Dr Liam Richard Sutton' _publ_contact_author_address ; Chemical & Process Engineering University of Sheffield Mappin St Sheffield S1 3JD UNITED KINGDOM ; _publ_contact_author_email 'L R SUTTON@YAHOO.CO.UK' _publ_section_title ; Tris(thioacetals) from benzene hexathiol: towards covalent self-assembly ; loop_ _publ_author_name 'Liam Richard Sutton' 'Wolfgang A. Donaubauer' 'Frank Hampel' 'Andreas Hirsch' data_ls02 _database_code_depnum_ccdc_archive 'CCDC 229167' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ; C~30~H~24~S~6~\.6H~2~O ; _chemical_formula_sum 'C30 H36 O6 S6' _chemical_formula_weight 684.95 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Rhombohedral _symmetry_space_group_name_H-M R-3 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z' '-x+y, -x, z' 'x+2/3, y+1/3, z+1/3' '-y+2/3, x-y+1/3, z+1/3' '-x+y+2/3, -x+1/3, z+1/3' 'x+1/3, y+2/3, z+2/3' '-y+1/3, x-y+2/3, z+2/3' '-x+y+1/3, -x+2/3, z+2/3' '-x, -y, -z' 'y, -x+y, -z' 'x-y, x, -z' '-x+2/3, -y+1/3, -z+1/3' 'y+2/3, -x+y+1/3, -z+1/3' 'x-y+2/3, x+1/3, -z+1/3' '-x+1/3, -y+2/3, -z+2/3' 'y+1/3, -x+y+2/3, -z+2/3' 'x-y+1/3, x+2/3, -z+2/3' _cell_length_a 15.7694(5) _cell_length_b 15.7694(5) _cell_length_c 25.0354(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 5391.6(3) _cell_formula_units_Z 6 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 6917 _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.266 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2160 _exptl_absorpt_coefficient_mu 0.418 _exptl_absorpt_correction_type 'empirical (Scalepack)' _exptl_absorpt_correction_T_min 0.8849 _exptl_absorpt_correction_T_max 0.9027 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean 9 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13583 _diffrn_reflns_av_R_equivalents 0.0578 _diffrn_reflns_av_sigmaI/netI 0.0327 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -30 _diffrn_reflns_limit_l_max 30 _diffrn_reflns_theta_min 2.21 _diffrn_reflns_theta_max 26.07 _reflns_number_total 2378 _reflns_number_gt 1975 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Nonius Collect' _computing_cell_refinement DENZO-SMN _computing_data_reduction DENZO-SMN _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHEXLTL NT' _computing_publication_material 'SHEXLTL NT' _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^)+(0.0902P)^2^+22.5867P] 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 'riding model' _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2378 _refine_ls_number_parameters 128 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0813 _refine_ls_R_factor_gt 0.0677 _refine_ls_wR_factor_ref 0.1874 _refine_ls_wR_factor_gt 0.1779 _refine_ls_goodness_of_fit_ref 1.116 _refine_ls_restrained_S_all 1.116 _refine_ls_shift/su_max 0.129 _refine_ls_shift/su_mean 0.009 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 C11 C 0.8041(3) 0.7487(3) 0.05061(15) 0.0370(8) Uani 1 1 d . . . H11A H 0.8138 0.7609 0.0113 0.044 Uiso 1 1 calc R . . S12 S 0.92016(6) 0.77260(6) 0.08009(4) 0.0378(3) Uani 1 1 d . . . C13 C 0.9692(2) 0.9003(2) 0.08002(14) 0.0342(7) Uani 1 1 d . . . C14 C 0.8998(2) 0.9321(2) 0.07984(14) 0.0336(7) Uani 1 1 d . . . S15 S 0.77647(6) 0.83856(6) 0.07987(4) 0.0379(3) Uani 1 1 d . . . C21 C 0.7236(3) 0.6454(3) 0.05932(16) 0.0384(8) Uani 1 1 d . . . C22 C 0.6942(3) 0.6058(3) 0.10909(19) 0.0580(12) Uani 1 1 d . . . H22A H 0.7250 0.6443 0.1398 0.070 Uiso 1 1 calc R . . C23 C 0.6201(4) 0.5101(4) 0.1148(2) 0.0689(14) Uani 1 1 d . . . H23A H 0.6007 0.4840 0.1497 0.083 Uiso 1 1 calc R . . C24 C 0.5739(3) 0.4520(3) 0.0721(2) 0.0628(13) Uani 1 1 d . . . C25 C 0.6036(4) 0.4917(4) 0.0221(3) 0.0821(17) Uani 1 1 d . . . H25A H 0.5725 0.4526 -0.0084 0.099 Uiso 1 1 calc R . . C26 C 0.6784(4) 0.5881(3) 0.0151(2) 0.0612(12) Uani 1 1 d . . . H26A H 0.6981 0.6142 -0.0199 0.073 Uiso 1 1 calc R . . C27 C 0.4917(5) 0.3460(4) 0.0788(4) 0.102(2) Uani 1 1 d . . . H27A H 0.4650 0.3367 0.1151 0.153 Uiso 1 1 calc R . . H27B H 0.5177 0.3018 0.0730 0.153 Uiso 1 1 calc R . . H27C H 0.4397 0.3316 0.0528 0.153 Uiso 1 1 calc R . . O1 O 0.6393(6) 0.5330(6) -0.1362(2) 0.141(2) Uani 1 1 d . . . H1A H 0.6239 0.4959 -0.1658 0.170 Uiso 1 1 d R . . H1B H 0.6770 0.5985 -0.1386 0.170 Uiso 1 1 d R . . O2 O 0.4983(6) 0.2982(6) -0.0951(3) 0.169(3) Uani 1 1 d . . . H2A H 0.5317 0.3496 -0.1171 0.203 Uiso 1 1 d R . . H2B H 0.4662 0.2371 -0.1085 0.203 Uiso 1 1 d 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 C11 0.0340(17) 0.0335(18) 0.0412(19) 0.0017(14) 0.0019(14) 0.0152(15) S12 0.0342(5) 0.0298(5) 0.0493(6) 0.0038(4) 0.0000(4) 0.0158(4) C13 0.0342(17) 0.0299(17) 0.0378(18) 0.0021(13) 0.0005(14) 0.0155(14) C14 0.0298(16) 0.0319(16) 0.0379(18) 0.0003(13) 0.0024(13) 0.0145(14) S15 0.0297(5) 0.0324(5) 0.0495(6) 0.0010(4) 0.0035(4) 0.0140(4) C21 0.0331(17) 0.0289(17) 0.051(2) -0.0003(15) -0.0010(15) 0.0139(14) C22 0.060(3) 0.043(2) 0.051(3) 0.0040(19) 0.003(2) 0.011(2) C23 0.065(3) 0.051(3) 0.071(3) 0.018(2) 0.012(2) 0.015(2) C24 0.044(2) 0.033(2) 0.099(4) 0.006(2) 0.003(2) 0.0099(18) C25 0.073(4) 0.054(3) 0.087(4) -0.021(3) -0.023(3) 0.008(3) C26 0.061(3) 0.049(2) 0.055(3) -0.003(2) -0.006(2) 0.012(2) C27 0.072(4) 0.037(3) 0.160(7) 0.008(3) 0.007(4) 0.000(3) O1 0.200(7) 0.207(7) 0.084(3) 0.008(4) 0.009(4) 0.152(6) O2 0.137(6) 0.175(7) 0.144(6) -0.010(5) -0.011(5) 0.039(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 C11 C21 1.499(5) . ? C11 S12 1.829(4) . ? C11 S15 1.831(4) . ? S12 C13 1.759(3) . ? C13 C14 1.379(5) 2_765 ? C13 C14 1.413(5) . ? C14 C13 1.379(5) 3_675 ? C14 S15 1.758(3) . ? C21 C22 1.367(6) . ? C21 C26 1.381(6) . ? C22 C23 1.378(6) . ? C23 C24 1.360(8) . ? C24 C25 1.372(8) . ? C24 C27 1.528(6) . ? C25 C26 1.393(7) . ? 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 C21 C11 S12 112.4(3) . . ? C21 C11 S15 112.5(2) . . ? S12 C11 S15 106.27(19) . . ? C13 S12 C11 93.26(16) . . ? C14 C13 C14 120.2(3) 2_765 . ? C14 C13 S12 124.3(3) 2_765 . ? C14 C13 S12 115.5(2) . . ? C13 C14 C13 119.8(3) 3_675 . ? C13 C14 S15 124.7(3) 3_675 . ? C13 C14 S15 115.5(2) . . ? C14 S15 C11 93.27(16) . . ? C22 C21 C26 119.1(4) . . ? C22 C21 C11 122.6(4) . . ? C26 C21 C11 118.3(4) . . ? C23 C22 C21 120.2(5) . . ? C24 C23 C22 122.1(5) . . ? C25 C24 C23 117.7(4) . . ? C25 C24 C27 120.7(5) . . ? C23 C24 C27 121.7(5) . . ? C24 C25 C26 121.6(5) . . ? C21 C26 C25 119.4(5) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 26.07 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.685 _refine_diff_density_min -0.456 _refine_diff_density_rms 0.087