Supplementary Material (ESI) for Chemical Communications This journal is © The Royal Society of Chemistry 2001 data_niels2 _database_code_CSD 164802 _journal_coden_Cambridge 182 _publ_requested_journal 'Chemical Communications' loop_ _publ_author_name 'Mogens Brondsted Nielsen' 'Nicolle N. P. Moonen' 'Corinne Boudon' 'Jean-Paul Gisselbrecht' 'Paul Seiler' 'Maurice Gross' 'Francois Diederich' _publ_contact_author_name 'Prof Francois Diederich' _publ_contact_author_address ; Prof Francois Diederich Laboratorium fur Organische Chemie ETH-Zentrum Universitatsstrasse 16 Zurich CH 8092 SWITZERLAND ; _publ_contact_author_email 'DIEDERICH@ORG.CHEM.ETHZ.CH' _publ_section_title ; Tetrathiafulvalene-acetylene scaffolding: new pi-electron systems for advanced materials ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety 'C20 H14 O8 S4' _chemical_formula_sum 'C20 H14 O8 S4' _chemical_formula_weight 510.55 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'S' 'S' 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/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 25.782(8) _cell_length_b 4.1070(10) _cell_length_c 21.947(5) _cell_angle_alpha 90.00 _cell_angle_beta 111.87(2) _cell_angle_gamma 90.00 _cell_volume 2156.6(10) _cell_formula_units_Z 4 _cell_measurement_temperature 248(2) _cell_measurement_reflns_used 16 _cell_measurement_theta_min 14.90 _cell_measurement_theta_max 26.40 _exptl_crystal_description 'Cut fragment' _exptl_crystal_colour orange _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.572 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1048 _exptl_absorpt_coefficient_mu 4.473 _exptl_absorpt_correction_type 'semi-empirical based on psi-scan' _exptl_absorpt_correction_T_min 0.51000 _exptl_absorpt_correction_T_max 0.99000 _exptl_special_details ; ? ; _diffrn_ambient_temperature 248(2) _diffrn_radiation_wavelength 1.54180 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'NONIUS CAD4' _diffrn_measurement_method '\q/\q' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 2 _diffrn_standards_interval_count ? _diffrn_standards_interval_time '167 min.' _diffrn_standards_decay_% 1.700 _diffrn_reflns_number 3841 _diffrn_reflns_av_R_equivalents 0.030 _diffrn_reflns_av_sigmaI/netI 0.0254 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 28 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 4 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 3.69 _diffrn_reflns_theta_max 60.00 _reflns_number_total 3214 _reflns_number_gt 2512 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CAD4 VMS-software (Nonius, 1989)' _computing_cell_refinement 'CAD4 VMS-software (Nonius, 1989)' _computing_data_reduction 'MOLEN VMS-software (Nonius, 1990)' _computing_structure_solution 'SIR92 (Altomare et al.,1994)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP (Johnson,1976)' _computing_publication_material 'SHELXL97' _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_weigthing_details 'w=1/[\s^2^(Fo^2^)+(0.1532P)^2^+7.3006P] 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 'H-atoms riding' _refine_ls_extinction_method 'SHELXL97' _refine_ls_extinction_coef 0.0001(2) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 3163 _refine_ls_number_parameters 295 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1106 _refine_ls_R_factor_gt 0.0931 _refine_ls_wR_factor_ref 0.2802 _refine_ls_wR_factor_gt 0.2552 _refine_ls_goodness_of_fit_ref 1.111 _refine_ls_restrained_S_all 1.111 _refine_ls_shift/su_max 0.141 _refine_ls_shift/su_mean 0.014 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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.1111(2) 0.0803(16) 0.0601(3) 0.0467(14) Uani 1 d . . . S2 S 0.17060(6) 0.1716(5) 0.12825(7) 0.0536(5) Uani 1 d . . . C3 C 0.1348(2) 0.3414(17) 0.1737(3) 0.0490(14) Uani 1 d . . . C4 C 0.0789(2) 0.3700(16) 0.1443(3) 0.0467(14) Uani 1 d . . . S5 S 0.04834(5) 0.2201(4) 0.06474(6) 0.0452(4) Uani 1 d . . . C6 C 0.0411(2) 0.5350(16) 0.1721(3) 0.0485(14) Uani 1 d . . . O7 O 0.0566(2) 0.7102(13) 0.2191(2) 0.0675(13) Uani 1 d . . . O8 O -0.01159(17) 0.4746(12) 0.1346(2) 0.0584(11) Uani 1 d . . . C9 C -0.0532(3) 0.635(2) 0.1544(3) 0.0643(18) Uani 1 d . . . H9A H -0.0903 0.5754 0.1244 0.15(5) Uiso 1 calc R . . H9B H -0.0485 0.8691 0.1536 0.020(11) Uiso 1 calc R . . H9C H -0.0483 0.5673 0.1986 0.12(3) Uiso 1 calc R . . C10 C 0.1707(3) 0.4575(18) 0.2412(3) 0.0565(16) Uani 1 d . . . O11 O 0.2096(3) 0.628(3) 0.2497(3) 0.159(4) Uani 1 d . . . O12 O 0.15658(19) 0.3319(15) 0.28671(19) 0.0717(15) Uani 1 d . . . C13 C 0.1879(3) 0.456(2) 0.3538(3) 0.073(2) Uani 1 d . . . H13A H 0.1746 0.3491 0.3846 0.247 Uiso 1 calc R . . H13B H 0.1821 0.6893 0.3549 0.361 Uiso 1 calc R . . H13C H 0.2274 0.4121 0.3658 0.259 Uiso 1 calc R . . C14 C 0.1134(3) -0.0894(18) 0.0076(3) 0.0552(15) Uani 1 d . . . H14A H 0.0800 -0.1286 -0.0284 0.11(3) Uiso 1 calc R . . C15 C 0.1638(3) -0.2079(17) 0.0052(3) 0.0535(16) Uani 1 d . . . C16 C 0.2083(3) -0.2904(19) 0.0049(3) 0.0591(18) Uani 1 d . . . C17 C 0.2576(3) -0.411(2) 0.0058(4) 0.072(2) Uani 1 d . . . C18 C 0.3025(3) -0.509(2) 0.0061(4) 0.082(2) Uani 1 d . . . C19 C 0.3545(3) -0.633(3) 0.0094(4) 0.084(3) Uani 1 d . . . H19A H 0.3788 -0.7259 0.0489 0.09(3) Uiso 1 calc R . . C20 C 0.3698(3) -0.622(2) -0.0420(4) 0.0628(17) Uani 1 d . . . S21 S 0.43415(8) -0.7578(6) -0.03968(12) 0.0810(7) Uani 1 d . . . C22 C 0.4218(7) -0.690(3) -0.1198(7) 0.135(5) Uani 1 d . . . C23 C 0.3755(8) -0.555(3) -0.1576(5) 0.151(7) Uani 1 d . . . S24 S 0.32796(11) -0.4696(6) -0.11849(11) 0.0997(9) Uani 1 d . . . C25 C 0.3707(6) -0.503(6) -0.2276(8) 0.170(7) Uani 1 d . . . O26 O 0.4124(5) -0.667(3) -0.2428(5) 0.199(5) Uani 1 d . . . O27 O 0.3303(3) -0.333(2) -0.2496(3) 0.133(3) Uani 1 d . . . C28 C 0.3109(4) -0.264(3) -0.3245(5) 0.100(3) Uani 1 d . . . C29 C 0.4889(3) -0.804(2) -0.1264(4) 0.0658(19) Uani 1 d . . . O30 O 0.5041(8) -1.059(7) -0.1097(12) 0.356(12) Uani 1 d . . . O31 O 0.5048(5) -0.614(4) -0.1478(7) 0.182(4) Uani 1 d . . . C32 C 0.5436(6) -0.775(5) -0.1641(7) 0.180(8) Uani 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 C1 0.045(3) 0.060(4) 0.041(3) 0.003(3) 0.023(2) 0.000(3) S2 0.0428(8) 0.0770(11) 0.0407(8) 0.0004(7) 0.0152(6) 0.0044(7) C3 0.043(3) 0.073(4) 0.033(3) 0.002(3) 0.017(2) -0.001(3) C4 0.052(3) 0.057(3) 0.036(3) 0.000(3) 0.021(2) -0.002(3) S5 0.0354(7) 0.0666(10) 0.0317(7) -0.0045(6) 0.0103(5) 0.0021(6) C6 0.049(3) 0.059(4) 0.042(3) 0.003(3) 0.022(2) 0.001(3) O7 0.064(3) 0.086(3) 0.052(3) -0.023(2) 0.021(2) -0.001(2) O8 0.051(2) 0.074(3) 0.056(2) -0.007(2) 0.0266(19) 0.003(2) C9 0.059(4) 0.080(5) 0.064(4) 0.004(4) 0.036(3) 0.012(4) C10 0.057(4) 0.066(4) 0.041(3) 0.001(3) 0.012(3) -0.008(3) O11 0.133(5) 0.283(11) 0.045(3) -0.008(5) 0.015(3) -0.139(7) O12 0.063(3) 0.119(4) 0.032(2) -0.005(2) 0.0158(19) -0.028(3) C13 0.076(4) 0.098(6) 0.033(3) -0.009(3) 0.008(3) -0.011(4) C14 0.058(3) 0.069(4) 0.045(3) -0.004(3) 0.026(3) -0.003(3) C15 0.058(4) 0.072(4) 0.036(3) 0.001(3) 0.024(3) 0.000(3) C16 0.056(4) 0.082(5) 0.043(3) -0.009(3) 0.024(3) -0.001(3) C17 0.061(4) 0.096(6) 0.070(4) -0.004(4) 0.040(3) -0.002(4) C18 0.074(5) 0.095(6) 0.088(5) -0.003(5) 0.044(4) 0.003(5) C19 0.065(4) 0.118(7) 0.076(5) 0.018(5) 0.035(4) 0.028(5) C20 0.049(3) 0.074(5) 0.070(4) 0.000(4) 0.027(3) 0.006(3) S21 0.0532(10) 0.0921(15) 0.1112(16) -0.0133(11) 0.0460(10) 0.0014(9) C22 0.238(13) 0.099(8) 0.144(9) -0.042(7) 0.156(9) -0.056(9) C23 0.33(2) 0.070(7) 0.073(6) -0.020(5) 0.099(10) -0.041(10) S24 0.1094(18) 0.0753(14) 0.0802(14) 0.0034(11) -0.0044(12) -0.0035(13) C25 0.154(11) 0.23(2) 0.172(13) -0.029(14) 0.116(11) -0.047(14) O26 0.246(10) 0.260(13) 0.172(8) -0.098(8) 0.173(8) -0.080(9) O27 0.078(4) 0.211(9) 0.088(4) -0.025(5) 0.004(3) 0.077(5) C28 0.095(6) 0.133(9) 0.070(5) 0.008(5) 0.029(5) 0.008(6) C29 0.065(4) 0.065(4) 0.070(4) 0.015(4) 0.027(4) 0.019(4) O30 0.312(18) 0.35(3) 0.53(3) 0.15(3) 0.30(2) 0.18(2) O31 0.164(9) 0.165(10) 0.249(13) -0.002(10) 0.112(9) 0.003(8) C32 0.138(10) 0.29(2) 0.125(9) -0.008(11) 0.063(8) 0.116(12) _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 C1 C14 1.367(9) . ? C1 S2 1.739(6) . ? C1 S5 1.755(6) . ? S2 C3 1.739(6) . ? C3 C4 1.346(8) . ? C3 C10 1.501(8) . ? C4 C6 1.492(8) . ? C4 S5 1.739(6) . ? C6 O7 1.198(7) . ? C6 O8 1.323(7) . ? O8 C9 1.456(8) . ? C10 O11 1.180(9) . ? C10 O12 1.292(8) . ? O12 C13 1.481(7) . ? C14 C15 1.408(9) . ? C15 C16 1.197(9) . ? C16 C17 1.357(10) . ? C17 C18 1.226(10) . ? C18 C19 1.410(11) . ? C19 C20 1.327(11) . ? C20 S21 1.735(7) . ? C20 S24 1.739(7) . ? S21 C22 1.689(13) . ? C22 C23 1.30(2) . ? C22 C29 1.849(16) . ? C23 C25 1.512(17) . ? C23 S24 1.773(17) . ? C25 O27 1.20(2) . ? C25 O26 1.41(2) . ? O27 C28 1.556(12) . ? C29 O31 1.070(14) . ? C29 O30 1.13(2) . ? C29 C32 1.886(17) . ? O31 C32 1.354(16) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C14 C1 S2 122.2(5) . . ? C14 C1 S5 123.2(5) . . ? S2 C1 S5 114.6(3) . . ? C3 S2 C1 95.3(3) . . ? C4 C3 C10 127.0(6) . . ? C4 C3 S2 117.5(4) . . ? C10 C3 S2 115.4(4) . . ? C3 C4 C6 126.1(5) . . ? C3 C4 S5 117.0(4) . . ? C6 C4 S5 116.8(4) . . ? C4 S5 C1 95.3(3) . . ? O7 C6 O8 125.6(6) . . ? O7 C6 C4 124.5(5) . . ? O8 C6 C4 109.7(5) . . ? C6 O8 C9 115.4(5) . . ? O11 C10 O12 125.7(6) . . ? O11 C10 C3 121.3(6) . . ? O12 C10 C3 112.8(6) . . ? C10 O12 C13 115.2(5) . . ? C1 C14 C15 122.6(6) . . ? C16 C15 C14 175.8(7) . . ? C15 C16 C17 175.0(8) . . ? C18 C17 C16 177.9(10) . . ? C17 C18 C19 176.8(9) . . ? C20 C19 C18 121.3(8) . . ? C19 C20 S21 123.2(6) . . ? C19 C20 S24 124.0(6) . . ? S21 C20 S24 112.7(4) . . ? C22 S21 C20 96.3(6) . . ? C23 C22 S21 120.5(10) . . ? C23 C22 C29 136.3(11) . . ? S21 C22 C29 102.8(10) . . ? C22 C23 C25 114.7(16) . . ? C22 C23 S24 114.4(8) . . ? C25 C23 S24 130.9(14) . . ? C20 S24 C23 96.0(5) . . ? O27 C25 O26 144.1(15) . . ? O27 C25 C23 102.8(13) . . ? O26 C25 C23 113.1(17) . . ? C25 O27 C28 114.8(10) . . ? O31 C29 O30 132.5(14) . . ? O31 C29 C22 111.9(10) . . ? O30 C29 C22 115.5(12) . . ? O31 C29 C32 44.7(9) . . ? O30 C29 C32 88.5(12) . . ? C22 C29 C32 153.2(8) . . ? C29 O31 C32 101.5(15) . . ? O31 C32 C29 33.8(8) . . ? 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 C14 C1 S2 C3 -174.5(6) . . . . ? S5 C1 S2 C3 4.9(4) . . . . ? C1 S2 C3 C4 -4.3(6) . . . . ? C1 S2 C3 C10 178.9(5) . . . . ? C10 C3 C4 C6 2.3(11) . . . . ? S2 C3 C4 C6 -174.1(5) . . . . ? C10 C3 C4 S5 178.6(5) . . . . ? S2 C3 C4 S5 2.2(7) . . . . ? C3 C4 S5 C1 1.1(6) . . . . ? C6 C4 S5 C1 177.8(5) . . . . ? C14 C1 S5 C4 175.4(6) . . . . ? S2 C1 S5 C4 -4.0(4) . . . . ? C3 C4 C6 O7 13.4(11) . . . . ? S5 C4 C6 O7 -163.0(6) . . . . ? C3 C4 C6 O8 -170.5(6) . . . . ? S5 C4 C6 O8 13.1(7) . . . . ? O7 C6 O8 C9 -1.1(9) . . . . ? C4 C6 O8 C9 -177.1(5) . . . . ? C4 C3 C10 O11 -126.5(10) . . . . ? S2 C3 C10 O11 50.0(11) . . . . ? C4 C3 C10 O12 58.3(10) . . . . ? S2 C3 C10 O12 -125.3(6) . . . . ? O11 C10 O12 C13 9.3(13) . . . . ? C3 C10 O12 C13 -175.6(6) . . . . ? S2 C1 C14 C15 1.2(10) . . . . ? S5 C1 C14 C15 -178.2(5) . . . . ? C1 C14 C15 C16 -40(9) . . . . ? C14 C15 C16 C17 144(9) . . . . ? C15 C16 C17 C18 178(100) . . . . ? C16 C17 C18 C19 140(19) . . . . ? C17 C18 C19 C20 160(18) . . . . ? C18 C19 C20 S21 177.6(7) . . . . ? C18 C19 C20 S24 -2.1(14) . . . . ? C19 C20 S21 C22 176.8(9) . . . . ? S24 C20 S21 C22 -3.5(6) . . . . ? C20 S21 C22 C23 3.7(12) . . . . ? C20 S21 C22 C29 177.2(6) . . . . ? S21 C22 C23 C25 178.6(10) . . . . ? C29 C22 C23 C25 8(2) . . . . ? S21 C22 C23 S24 -2.5(15) . . . . ? C29 C22 C23 S24 -173.2(9) . . . . ? C19 C20 S24 C23 -177.8(9) . . . . ? S21 C20 S24 C23 2.5(6) . . . . ? C22 C23 S24 C20 -0.2(11) . . . . ? C25 C23 S24 C20 178.5(14) . . . . ? C22 C23 C25 O27 -169.3(13) . . . . ? S24 C23 C25 O27 12(2) . . . . ? C22 C23 C25 O26 12(2) . . . . ? S24 C23 C25 O26 -167.1(10) . . . . ? O26 C25 O27 C28 5(3) . . . . ? C23 C25 O27 C28 -174.0(10) . . . . ? C23 C22 C29 O31 45(2) . . . . ? S21 C22 C29 O31 -126.7(11) . . . . ? C23 C22 C29 O30 -132(2) . . . . ? S21 C22 C29 O30 56.0(18) . . . . ? C23 C22 C29 C32 20(3) . . . . ? S21 C22 C29 C32 -152.0(17) . . . . ? O30 C29 O31 C32 13(3) . . . . ? C22 C29 O31 C32 -164.1(10) . . . . ? O30 C29 C32 O31 -171(2) . . . . ? C22 C29 C32 O31 34(2) . . . . ? _diffrn_measured_fraction_theta_max 0.846 _diffrn_reflns_theta_full 60.00 _diffrn_measured_fraction_theta_full 0.846 _refine_diff_density_max 0.759 _refine_diff_density_min -0.672 _refine_diff_density_rms 0.117 -- Paul Seiler Lab. fuer Org. Chemie Universitaetstr. 16 CH-8092 Zuerich Tel 41(1)6324508 Fax 41(1)6321072 E-mail seiler@org.chem.ethz.ch