# Supplementary Material (ESI) for Perkin Transactions # This journal is © The Royal Society of Chemistry 2002 data_ditio _database_code_CSD 185122 _journal_coden_Cambridge 188 _publ_requested_journal 'Perkin Transactions 2' loop_ _publ_author_name 'Gallazzi, Maria C.' 'Albertin, Luca' 'Bertarelli, Chiara' 'Meille, Stefano V.' _publ_contact_author_name 'Prof Maria C. Gallazzi' _publ_contact_author_address ; Chimica, Materiali e Ing.Chimica Politecnico di Milano piazza Leonardo da Vinci 32 Milan 20133 ITALY ; _publ_contact_author_email 'MARIA.GALLAZZI@POLIMI.IT' _publ_section_title ; Synthesis and characterisation of 1,2-difluoro-1,2-bis(5-trimethysilylthiophen-2-yl)ethenes. A new family of conjugated monomers for oxidative polymerisation. ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; (E)-1,2-difluoro-1,2-bis-(4-methoxy-5-trimethylsilyl-2-thienyl)ethene ; _chemical_formula_moiety 'C18 H26 F2 O2 S2 Si2' _chemical_formula_sum 'C18 H26 F2 O2 S2 Si2' _chemical_formula_weight 432.69 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'F' 'F' 0.0171 0.0103 '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' 'Si' 'Si' 0.0817 0.0704 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 15.537(3) _cell_length_b 16.739(2) _cell_length_c 10.481(2) _cell_angle_alpha 90.00 _cell_angle_beta 126.46(2) _cell_angle_gamma 90.00 _cell_volume 2192.3(7) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2894 _cell_measurement_theta_min 3.21 _cell_measurement_theta_max 23.09 _exptl_crystal_description needle _exptl_crystal_colour 'dark red' _exptl_crystal_size_max 0.1 _exptl_crystal_size_mid 0.02 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.311 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 912 _exptl_absorpt_coefficient_mu 0.379 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; '178 images of 2\%' ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.70000 _diffrn_radiation_type x-ray _diffrn_radiation_source 'synchrotron' _diffrn_radiation_monochromator 'Si(111)' _diffrn_measurement_device_type 'MAR345 image plate' _diffrn_measurement_method 'area detector' _diffrn_detector_area_resol_mean 0.70 _diffrn_reflns_number 22604 _diffrn_reflns_av_R_equivalents 0.0364 _diffrn_reflns_av_sigmaI/netI 0.0160 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 3.21 _diffrn_reflns_theta_max 29.91 _reflns_number_total 3262 _reflns_number_gt 3215 _reflns_threshold_expression >2sigma(I) _computing_data_collection MAR345 _computing_cell_refinement 'CrysAlisRED (OxfordDiffraction, 2001)' _computing_data_reduction 'CrysAlisRED (OxfordDiffraction, 2001)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'WINGX32 (Farrugia, 1999)' _computing_publication_material 'Ciftab (Sheldrick, 1986)' _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^)+(0.0339P)^2^+4.8993P] 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 mixed _refine_ls_extinction_method none _refine_ls_number_reflns 3262 _refine_ls_number_parameters 162 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0389 _refine_ls_R_factor_gt 0.0369 _refine_ls_wR_factor_ref 0.0975 _refine_ls_wR_factor_gt 0.0852 _refine_ls_goodness_of_fit_ref 1.136 _refine_ls_restrained_S_all 1.136 _refine_ls_shift/su_max 0.011 _refine_ls_shift/su_mean 0.001 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 0.88680(3) 0.21341(2) 0.40365(5) 0.01430(10) Uani 1 1 d . . . S1 S 0.67344(3) 0.12200(2) 0.15178(4) 0.01408(10) Uani 1 1 d . . . F1 F 0.51794(8) -0.07116(6) 0.13618(11) 0.0240(2) Uani 1 1 d . . . O1 O 0.87283(9) 0.06685(7) 0.59131(13) 0.0213(2) Uani 1 1 d . . . C1 C 0.53577(11) -0.00648(9) 0.07807(16) 0.0146(3) Uani 1 1 d . . . C2 C 0.63089(11) 0.03768(9) 0.19422(16) 0.0137(2) Uani 1 1 d . . . C3 C 0.70151(11) 0.01714(9) 0.35196(17) 0.0155(3) Uani 1 1 d . . . H3 H 0.6912(17) -0.0277(13) 0.396(2) 0.018(5) Uiso 1 1 d . . . C4 C 0.78961(11) 0.07071(9) 0.43438(16) 0.0140(3) Uani 1 1 d . . . C5 C 0.78721(11) 0.13118(9) 0.34302(16) 0.0143(3) Uani 1 1 d . . . C6 C 0.86675(13) 0.00590(11) 0.68084(18) 0.0214(3) Uani 1 1 d . . . H6A H 0.9314(19) 0.0103(14) 0.786(3) 0.025(3) Uiso 1 1 d . . . H6B H 0.8044(19) 0.0134(14) 0.680(3) 0.025(3) Uiso 1 1 d . . . H6C H 0.8636(18) -0.0478(14) 0.640(3) 0.025(3) Uiso 1 1 d . . . C7 C 0.87195(16) 0.29175(12) 0.5154(2) 0.0277(4) Uani 1 1 d . . . H7A H 0.802(2) 0.3146(17) 0.449(3) 0.047(4) Uiso 1 1 d . . . H7B H 0.928(2) 0.3337(18) 0.555(3) 0.047(4) Uiso 1 1 d . . . H7C H 0.880(2) 0.2704(17) 0.605(3) 0.047(4) Uiso 1 1 d . . . C8 C 1.02436(13) 0.17062(11) 0.5286(2) 0.0260(3) Uani 1 1 d . . . H8A H 1.030(2) 0.1277(18) 0.475(4) 0.048(5) Uiso 1 1 d . . . H8B H 1.074(2) 0.2098(18) 0.543(3) 0.048(5) Uiso 1 1 d . . . H8C H 1.045(2) 0.1531(18) 0.636(3) 0.048(5) Uiso 1 1 d . . . C9 C 0.85767(16) 0.25580(12) 0.2171(2) 0.0267(4) Uani 1 1 d . . . H9A H 0.908(2) 0.2964(18) 0.241(3) 0.051(5) Uiso 1 1 d . . . H9B H 0.788(3) 0.2806(18) 0.155(4) 0.051(5) Uiso 1 1 d . . . H9C H 0.858(2) 0.2151(18) 0.153(4) 0.051(5) 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 Si1 0.01325(18) 0.0146(2) 0.01421(18) -0.00236(13) 0.00771(15) -0.00381(13) S1 0.01146(15) 0.01340(17) 0.01332(16) 0.00035(11) 0.00515(13) -0.00113(11) F1 0.0218(5) 0.0221(5) 0.0168(4) 0.0030(4) 0.0054(4) -0.0099(4) O1 0.0163(5) 0.0261(6) 0.0126(5) 0.0016(4) 0.0037(4) -0.0086(4) C1 0.0107(6) 0.0147(6) 0.0154(7) -0.0001(5) 0.0061(5) -0.0015(5) C2 0.0110(6) 0.0144(6) 0.0140(6) -0.0004(5) 0.0065(5) -0.0010(5) C3 0.0122(6) 0.0166(7) 0.0139(6) 0.0014(5) 0.0057(5) -0.0024(5) C4 0.0103(5) 0.0161(6) 0.0111(6) -0.0012(5) 0.0039(5) -0.0019(5) C5 0.0121(6) 0.0148(6) 0.0134(6) -0.0016(5) 0.0062(5) -0.0022(5) C6 0.0193(7) 0.0240(8) 0.0145(6) 0.0037(6) 0.0065(6) -0.0049(6) C7 0.0316(9) 0.0243(8) 0.0348(9) -0.0128(7) 0.0238(8) -0.0094(7) C8 0.0148(7) 0.0242(8) 0.0317(9) -0.0015(7) 0.0097(6) -0.0035(6) C9 0.0303(9) 0.0281(9) 0.0196(7) -0.0002(6) 0.0136(7) -0.0107(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 Si1 C7 1.8613(18) . ? Si1 C8 1.8625(18) . ? Si1 C9 1.8650(18) . ? Si1 C5 1.8772(15) . ? S1 C5 1.7189(16) . ? S1 C2 1.7253(15) . ? F1 C1 1.3492(17) . ? O1 C4 1.3614(17) . ? O1 C6 1.4268(19) . ? C1 C1 1.341(3) 5_655 ? C1 C2 1.4402(19) . ? C2 C3 1.378(2) . ? C3 C4 1.4208(19) . ? C4 C5 1.379(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 C7 Si1 C8 110.37(9) . . ? C7 Si1 C9 110.35(10) . . ? C8 Si1 C9 110.21(9) . . ? C7 Si1 C5 110.13(8) . . ? C8 Si1 C5 109.06(8) . . ? C9 Si1 C5 106.64(8) . . ? C5 S1 C2 93.36(7) . . ? C4 O1 C6 116.23(12) . . ? C1 C1 F1 115.91(16) 5_655 . ? C1 C1 C2 129.68(17) 5_655 . ? F1 C1 C2 114.41(12) . . ? C3 C2 C1 124.84(13) . . ? C3 C2 S1 111.08(11) . . ? C1 C2 S1 124.05(11) . . ? C2 C3 C4 111.37(13) . . ? O1 C4 C5 119.22(12) . . ? O1 C4 C3 125.78(13) . . ? C5 C4 C3 114.99(13) . . ? C4 C5 S1 109.20(10) . . ? C4 C5 Si1 128.80(11) . . ? S1 C5 Si1 122.00(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 C1 C1 C2 C3 -177.4(2) 5_655 . . . ? F1 C1 C2 C3 1.4(2) . . . . ? C1 C1 C2 S1 0.5(3) 5_655 . . . ? F1 C1 C2 S1 179.22(10) . . . . ? C5 S1 C2 C3 0.63(12) . . . . ? C5 S1 C2 C1 -177.49(13) . . . . ? C1 C2 C3 C4 177.59(13) . . . . ? S1 C2 C3 C4 -0.52(16) . . . . ? C6 O1 C4 C5 176.12(14) . . . . ? C6 O1 C4 C3 -3.6(2) . . . . ? C2 C3 C4 O1 179.85(14) . . . . ? C2 C3 C4 C5 0.09(19) . . . . ? O1 C4 C5 S1 -179.40(11) . . . . ? C3 C4 C5 S1 0.37(17) . . . . ? O1 C4 C5 Si1 0.6(2) . . . . ? C3 C4 C5 Si1 -179.64(11) . . . . ? C2 S1 C5 C4 -0.56(12) . . . . ? C2 S1 C5 Si1 179.45(9) . . . . ? C7 Si1 C5 C4 -76.32(16) . . . . ? C8 Si1 C5 C4 44.94(16) . . . . ? C9 Si1 C5 C4 163.94(14) . . . . ? C7 Si1 C5 S1 103.66(11) . . . . ? C8 Si1 C5 S1 -135.08(10) . . . . ? C9 Si1 C5 S1 -16.08(12) . . . . ? _diffrn_measured_fraction_theta_max 0.981 _diffrn_reflns_theta_full 29.91 _diffrn_measured_fraction_theta_full 0.981 _refine_diff_density_max 0.554 _refine_diff_density_min -0.332 _refine_diff_density_rms 0.083