# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2008 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Regis Reau' _publ_contact_author_email REGIS.REAU@UNIV-RENNES1.FR _publ_section_title ; Synthesis, Electronic Properties and Electropolymerisation of EDOT-capped sigma3-Phospholes ; loop_ _publ_author_name 'Regis Reau' 'Peter Bauerle' 'Dolores Caras-Quintero' 'Muriel Hissler' 'Tamas Karpati' ; V.L.d.Talance ; 'Laszlo Nyulaszi' 'Regis Raau' 'Ling-Zhi Zhang.' # Attachment 'lc_lz05.cif' data_lc_lz05 _database_code_depnum_ccdc_archive 'CCDC 671173' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C26 H23 O4 P S2' _chemical_formula_sum 'C26 H23 O4 P S2' _chemical_formula_weight 494.53 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' P P 0.1023 0.0942 '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 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 11.081(2) _cell_length_b 14.186(2) _cell_length_c 15.345(3) _cell_angle_alpha 90 _cell_angle_beta 104.749(7) _cell_angle_gamma 90 _cell_volume 2332.7(7) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 5531 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.46 _exptl_crystal_description block _exptl_crystal_colour orange _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.408 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1032 _exptl_absorpt_coefficient_mu 0.329 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type CCD _diffrn_measurement_method none _diffrn_detector_area_resol_mean 9 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% none _diffrn_reflns_number 10378 _diffrn_reflns_av_R_equivalents 0.0200 _diffrn_reflns_av_sigmaI/netI 0.0319 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.91 _diffrn_reflns_theta_max 27.46 _reflns_number_total 5329 _reflns_number_gt 4042 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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^)+(0.0846P)^2^+0.9525P] 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 SHELXL _refine_ls_extinction_coef 0.008(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 5329 _refine_ls_number_parameters 299 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0680 _refine_ls_R_factor_gt 0.0507 _refine_ls_wR_factor_ref 0.1570 _refine_ls_wR_factor_gt 0.1416 _refine_ls_goodness_of_fit_ref 1.059 _refine_ls_restrained_S_all 1.059 _refine_ls_shift/su_max 0.001 _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 P1 P 0.83437(5) 0.13500(4) 0.75103(4) 0.04033(18) Uani 1 1 d . . . S1 S 1.14244(6) 0.15553(5) 1.00814(5) 0.0601(2) Uani 1 1 d . . . S2 S 0.54396(6) 0.13596(4) 0.61066(4) 0.04948(19) Uani 1 1 d . . . O1 O 1.08765(17) 0.17580(14) 0.74998(12) 0.0580(5) Uani 1 1 d . . . O2 O 1.34384(19) 0.2120(2) 0.84188(19) 0.0873(7) Uani 1 1 d . . . O3 O 0.51072(16) -0.07244(12) 0.76622(11) 0.0529(4) Uani 1 1 d . . . O4 O 0.31600(17) -0.07283(14) 0.59991(12) 0.0626(5) Uani 1 1 d . . . C8 C 0.69631(19) 0.09150(16) 0.77919(14) 0.0407(5) Uani 1 1 d . . . C7 C 0.7118(2) 0.09141(16) 0.87001(15) 0.0414(5) Uani 1 1 d . . . C6 C 0.6110(2) 0.0738(2) 0.91755(16) 0.0520(6) Uani 1 1 d . . . H6A H 0.6017 0.0064 0.9243 0.062 Uiso 1 1 calc R . . H6B H 0.5325 0.0980 0.8811 0.062 Uiso 1 1 calc R . . C5 C 0.6398(3) 0.1197(3) 1.0091(2) 0.0768(9) Uani 1 1 d . . . H5A H 0.6335 0.1876 1.0017 0.092 Uiso 1 1 calc R . . H5B H 0.5783 0.1000 1.0405 0.092 Uiso 1 1 calc R . . C4 C 0.7651(3) 0.0956(3) 1.0642(2) 0.0855(11) Uani 1 1 d . . . H4A H 0.7687 0.0281 1.0749 0.103 Uiso 1 1 calc R . . H4B H 0.7782 0.1267 1.1221 0.103 Uiso 1 1 calc R . . C3 C 0.8707(2) 0.1230(2) 1.02209(16) 0.0581(7) Uani 1 1 d . . . H3A H 0.8946 0.1877 1.0384 0.070 Uiso 1 1 calc R . . H3B H 0.9424 0.0834 1.0475 0.070 Uiso 1 1 calc R . . C2 C 0.8387(2) 0.11428(16) 0.92087(14) 0.0421(5) Uani 1 1 d . . . C1 C 0.9202(2) 0.13051(15) 0.86864(14) 0.0405(5) Uani 1 1 d . . . C15 C 1.0529(2) 0.15166(16) 0.89685(16) 0.0442(5) Uani 1 1 d . . . C16 C 1.1290(2) 0.17202(17) 0.84134(17) 0.0491(5) Uani 1 1 d . . . C17 C 1.1879(3) 0.1656(3) 0.7064(3) 0.0844(10) Uani 1 1 d . . . H17A H 1.1574 0.1802 0.6429 0.101 Uiso 1 1 calc R . . H17B H 1.2168 0.1008 0.7118 0.101 Uiso 1 1 calc R . . C18 C 1.2924(3) 0.2287(4) 0.7472(3) 0.1010(13) Uani 1 1 d . . . H18A H 1.3577 0.2207 0.7161 0.121 Uiso 1 1 calc R . . H18B H 1.2638 0.2935 0.7387 0.121 Uiso 1 1 calc R . . C19 C 1.2546(2) 0.1914(2) 0.8871(2) 0.0623(7) Uani 1 1 d . . . C20 C 1.2757(2) 0.1846(2) 0.9770(2) 0.0700(8) Uani 1 1 d . . . H20 H 1.3529 0.1945 1.0173 0.084 Uiso 1 1 calc R . . C9 C 0.5839(2) 0.06931(16) 0.70895(14) 0.0407(5) Uani 1 1 d . . . C10 C 0.50174(19) -0.00366(16) 0.70212(14) 0.0408(5) Uani 1 1 d . . . C11 C 0.4071(4) -0.1326(3) 0.7469(3) 0.0995(14) Uani 1 1 d . . . H11A H 0.4359 -0.1939 0.7716 0.119 Uiso 1 1 calc R . . H11B H 0.3500 -0.1096 0.7806 0.119 Uiso 1 1 calc R . . C12 C 0.3400(5) -0.1466(3) 0.6620(3) 0.125(2) Uani 1 1 d . . . H12A H 0.2599 -0.1718 0.6653 0.151 Uiso 1 1 calc R . . H12B H 0.3815 -0.1958 0.6367 0.151 Uiso 1 1 calc R . . C13 C 0.4069(2) -0.00446(17) 0.61979(15) 0.0453(5) Uani 1 1 d . . . C14 C 0.4173(2) 0.06677(19) 0.56378(16) 0.0522(6) Uani 1 1 d . . . H14 H 0.3631 0.0769 0.5074 0.063 Uiso 1 1 calc R . . C21 C 0.88673(19) 0.03539(16) 0.69533(14) 0.0407(5) Uani 1 1 d . . . C22 C 0.8601(2) 0.0358(2) 0.60212(16) 0.0513(6) Uani 1 1 d . . . H22 H 0.8146 0.0852 0.5698 0.062 Uiso 1 1 calc R . . C23 C 0.9012(3) -0.0376(2) 0.55677(18) 0.0600(7) Uani 1 1 d . . . H23 H 0.8812 -0.0379 0.4941 0.072 Uiso 1 1 calc R . . C24 C 0.9707(3) -0.1091(2) 0.6038(2) 0.0645(7) Uani 1 1 d . . . H24 H 1.0000 -0.1571 0.5733 0.077 Uiso 1 1 calc R . . C25 C 0.9971(3) -0.1101(2) 0.6962(2) 0.0714(8) Uani 1 1 d . . . H25 H 1.0440 -0.1592 0.7280 0.086 Uiso 1 1 calc R . . C26 C 0.9549(3) -0.03910(18) 0.74224(17) 0.0591(7) Uani 1 1 d . . . H26 H 0.9720 -0.0411 0.8048 0.071 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 P1 0.0404(3) 0.0424(3) 0.0360(3) 0.0015(2) 0.0056(2) -0.0030(2) S1 0.0469(4) 0.0738(5) 0.0507(4) -0.0074(3) -0.0039(3) -0.0030(3) S2 0.0499(3) 0.0528(4) 0.0412(3) 0.0078(2) 0.0032(2) -0.0064(2) O1 0.0510(10) 0.0695(12) 0.0556(10) 0.0015(9) 0.0171(8) -0.0085(8) O2 0.0439(11) 0.1104(19) 0.1090(19) 0.0142(15) 0.0220(11) -0.0091(11) O3 0.0553(10) 0.0490(9) 0.0478(9) 0.0106(7) 0.0012(7) -0.0081(7) O4 0.0561(10) 0.0674(12) 0.0544(10) 0.0045(9) -0.0040(8) -0.0219(9) C8 0.0371(10) 0.0444(12) 0.0370(10) 0.0005(9) 0.0027(8) -0.0010(8) C7 0.0381(11) 0.0432(12) 0.0415(11) 0.0000(9) 0.0078(8) 0.0000(9) C6 0.0432(12) 0.0703(16) 0.0441(12) -0.0011(11) 0.0143(10) -0.0001(11) C5 0.0592(17) 0.121(3) 0.0546(16) -0.0188(17) 0.0222(13) -0.0014(17) C4 0.0665(19) 0.148(4) 0.0439(15) -0.0061(19) 0.0174(13) -0.003(2) C3 0.0514(14) 0.0843(19) 0.0368(12) -0.0070(12) 0.0077(10) -0.0050(13) C2 0.0419(11) 0.0459(12) 0.0360(11) -0.0020(9) 0.0056(8) 0.0004(9) C1 0.0399(11) 0.0409(11) 0.0371(11) -0.0012(8) 0.0032(8) -0.0029(8) C15 0.0394(11) 0.0447(12) 0.0439(12) -0.0038(9) 0.0021(9) -0.0024(9) C16 0.0425(12) 0.0455(12) 0.0576(14) -0.0029(11) 0.0094(10) -0.0043(9) C17 0.069(2) 0.113(3) 0.082(2) 0.007(2) 0.0388(17) -0.0020(19) C18 0.065(2) 0.139(4) 0.106(3) 0.018(3) 0.035(2) -0.015(2) C19 0.0409(13) 0.0592(16) 0.084(2) 0.0005(14) 0.0109(13) -0.0039(11) C20 0.0387(13) 0.081(2) 0.079(2) -0.0029(16) -0.0056(12) -0.0082(13) C9 0.0380(10) 0.0450(12) 0.0362(10) 0.0016(9) 0.0039(8) 0.0008(9) C10 0.0395(10) 0.0432(11) 0.0370(11) 0.0030(9) 0.0045(8) 0.0023(9) C11 0.089(2) 0.103(3) 0.086(2) 0.042(2) -0.0145(19) -0.050(2) C12 0.140(4) 0.101(3) 0.097(3) 0.043(2) -0.042(3) -0.077(3) C13 0.0406(11) 0.0516(13) 0.0397(11) -0.0022(10) 0.0030(9) -0.0057(9) C14 0.0458(12) 0.0638(15) 0.0396(12) 0.0051(11) -0.0027(9) -0.0040(11) C21 0.0397(10) 0.0429(11) 0.0371(11) 0.0006(9) 0.0056(8) -0.0045(8) C22 0.0492(13) 0.0635(15) 0.0393(12) 0.0016(11) 0.0081(10) 0.0029(11) C23 0.0603(15) 0.0747(18) 0.0450(13) -0.0130(12) 0.0136(11) -0.0038(13) C24 0.0707(18) 0.0540(15) 0.0695(18) -0.0173(14) 0.0194(14) -0.0066(13) C25 0.088(2) 0.0428(14) 0.074(2) -0.0007(13) 0.0036(16) 0.0096(14) C26 0.0826(18) 0.0463(14) 0.0429(13) 0.0030(10) 0.0057(12) 0.0038(13) _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 P1 C8 1.801(2) . ? P1 C1 1.814(2) . ? P1 C21 1.821(2) . ? S1 C20 1.715(3) . ? S1 C15 1.744(2) . ? S2 C14 1.714(3) . ? S2 C9 1.739(2) . ? O1 C16 1.361(3) . ? O1 C17 1.441(4) . ? O2 C19 1.375(4) . ? O2 C18 1.439(5) . ? O3 C10 1.371(3) . ? O3 C11 1.401(3) . ? O4 C13 1.375(3) . ? O4 C12 1.395(4) . ? C8 C7 1.360(3) . ? C8 C9 1.459(3) . ? C7 C2 1.461(3) . ? C7 C6 1.502(3) . ? C6 C5 1.508(4) . ? C5 C4 1.470(4) . ? C4 C3 1.524(4) . ? C3 C2 1.508(3) . ? C2 C1 1.371(3) . ? C1 C15 1.455(3) . ? C15 C16 1.373(3) . ? C16 C19 1.417(3) . ? C17 C18 1.472(5) . ? C19 C20 1.343(4) . ? C9 C10 1.365(3) . ? C10 C13 1.423(3) . ? C11 C12 1.339(5) . ? C13 C14 1.351(3) . ? C21 C22 1.385(3) . ? C21 C26 1.389(3) . ? C22 C23 1.392(4) . ? C23 C24 1.363(4) . ? C24 C25 1.373(4) . ? C25 C26 1.379(4) . ? 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 C8 P1 C1 90.67(10) . . ? C8 P1 C21 103.78(10) . . ? C1 P1 C21 106.89(10) . . ? C20 S1 C15 92.85(14) . . ? C14 S2 C9 93.03(11) . . ? C16 O1 C17 112.1(2) . . ? C19 O2 C18 113.1(2) . . ? C10 O3 C11 112.1(2) . . ? C13 O4 C12 112.1(2) . . ? C7 C8 C9 128.1(2) . . ? C7 C8 P1 110.67(16) . . ? C9 C8 P1 120.96(16) . . ? C8 C7 C2 113.58(19) . . ? C8 C7 C6 125.6(2) . . ? C2 C7 C6 120.8(2) . . ? C7 C6 C5 111.9(2) . . ? C4 C5 C6 112.3(3) . . ? C5 C4 C3 114.3(3) . . ? C2 C3 C4 114.3(2) . . ? C1 C2 C7 114.40(19) . . ? C1 C2 C3 124.9(2) . . ? C7 C2 C3 120.7(2) . . ? C2 C1 C15 128.8(2) . . ? C2 C1 P1 109.31(16) . . ? C15 C1 P1 121.55(17) . . ? C16 C15 C1 126.3(2) . . ? C16 C15 S1 108.36(17) . . ? C1 C15 S1 125.30(19) . . ? O1 C16 C15 123.3(2) . . ? O1 C16 C19 122.2(2) . . ? C15 C16 C19 114.5(2) . . ? O1 C17 C18 111.0(3) . . ? O2 C18 C17 113.3(3) . . ? C20 C19 O2 125.0(3) . . ? C20 C19 C16 112.8(3) . . ? O2 C19 C16 122.2(3) . . ? C19 C20 S1 111.5(2) . . ? C10 C9 C8 130.4(2) . . ? C10 C9 S2 109.17(16) . . ? C8 C9 S2 120.27(17) . . ? C9 C10 O3 124.02(19) . . ? C9 C10 C13 113.7(2) . . ? O3 C10 C13 122.2(2) . . ? C12 C11 O3 121.2(3) . . ? C11 C12 O4 121.0(3) . . ? C14 C13 O4 124.3(2) . . ? C14 C13 C10 113.3(2) . . ? O4 C13 C10 122.4(2) . . ? C13 C14 S2 110.80(17) . . ? C22 C21 C26 118.9(2) . . ? C22 C21 P1 118.15(18) . . ? C26 C21 P1 122.92(18) . . ? C21 C22 C23 120.2(2) . . ? C24 C23 C22 120.3(3) . . ? C23 C24 C25 119.8(3) . . ? C24 C25 C26 120.7(3) . . ? C25 C26 C21 120.1(2) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.46 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.503 _refine_diff_density_min -0.431 _refine_diff_density_rms 0.053