# Supplementary Material (ESI) for Journal of Materials Chemistry # This journal is © The Royal Society of Chemistry 2005 data_global _journal_name_full J.Mater.Chem. _journal_coden_Cambridge 1145 _publ_contact_author_name 'Dr J Roncali' _publ_contact_author_address ; CNRS CIMMA 2 Bd Laboisier Angers 49045 FRANCE ; _publ_contact_author_email JEAN.RONCALI@UNIV-ANGERS.FR _publ_section_title ; Structure-Reactivity Relationships in Bithiophenic Precursors based on the 3-Phenoxythiophene Building Block ; loop_ _publ_author_name 'J. Roncali' 'Pierre Frere' 'Philippe Leriche' data_lph625 _database_code_depnum_ccdc_archive 'CCDC 263331' _audit_creation_date 2005-05-03T16:28:05-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C11 H9 O1 S1' _chemical_formula_sum 'C11 H9 O S' _chemical_formula_weight 189.24 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P b c n' _symmetry_space_group_name_Hall '-P 2n 2ab' _symmetry_Int_Tables_number 60 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y, -z+1/2' '-x, -y, -z' 'x-1/2, y-1/2, -z-1/2' '-x-1/2, y-1/2, z' 'x, -y, z-1/2' _cell_length_a 19.056(2) _cell_length_b 7.536(1) _cell_length_c 13.524(1) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 1942.1(4) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 5731 _cell_measurement_theta_min 1.85 _cell_measurement_theta_max 25.4 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour orange _exptl_crystal_size_max 0.62 _exptl_crystal_size_mid 0.33 _exptl_crystal_size_min 0.19 _exptl_crystal_density_diffrn 1.294 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 792 loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 1 0 0 0.116 -1 0 0 0.077 0 1 0 0.308 0 -1 0 0.308 0 0 1 0.173 0 0 -1 0.154 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.287 _exptl_absorpt_correction_type gaussian _exptl_absorpt_process_details ; ? ; _exptl_absorpt_correction_T_min 0.8855 _exptl_absorpt_correction_T_max 0.9474 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_detector_area_resol_mean 6.66 _diffrn_measurement_device_type 'STOE IPDS' _diffrn_measurement_method 'Oscillation Phi Incr 1.2 deg' _diffrn_reflns_av_R_equivalents 0.0741 _diffrn_reflns_av_unetI/netI 0.046 _diffrn_reflns_number 10599 _diffrn_reflns_limit_h_min -23 _diffrn_reflns_limit_h_max 23 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.91 _diffrn_reflns_theta_max 25.81 _diffrn_reflns_theta_full 25.81 _diffrn_measured_fraction_theta_full 0.992 _diffrn_measured_fraction_theta_max 0.992 _reflns_number_total 1859 _reflns_number_gt 1139 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'EXPOSE, STOE IPDS' _computing_cell_refinement 'SELECT,CELL, STOE IPDS' _computing_data_reduction 'INTEGRATE, STOE IPDS' _computing_structure_solution 'Direct methods (Sir92,Altomare et al.,1993)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'DIAMOND 2.1e (Crystal Impact gbr 2001)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0759P)^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 mixed _refine_ls_extinction_method none _refine_ls_number_reflns 1859 _refine_ls_number_parameters 154 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0776 _refine_ls_R_factor_gt 0.0461 _refine_ls_wR_factor_ref 0.129 _refine_ls_wR_factor_gt 0.1163 _refine_ls_goodness_of_fit_ref 0.971 _refine_ls_restrained_S_all 0.971 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.297 _refine_diff_density_min -0.185 _refine_diff_density_rms 0.037 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.006 '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' 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 C01 C 0.48503(11) 0.5673(3) 0.53219(17) 0.0637(6) Uani 1 1 d . . . C02 C 0.42331(13) 0.5617(3) 0.58349(19) 0.0734(7) Uani 1 1 d . . . C03 C 0.40716(18) 0.7174(4) 0.6361(2) 0.0952(9) Uani 1 1 d . . . C04 C 0.4567(2) 0.8388(5) 0.6243(3) 0.1049(11) Uani 1 1 d . . . C05 C 0.36290(10) 0.3245(3) 0.66179(17) 0.0628(6) Uani 1 1 d . . . C06 C 0.39808(13) 0.3427(4) 0.7494(2) 0.0828(8) Uani 1 1 d . . . C07 C 0.37771(15) 0.2417(4) 0.8286(2) 0.0871(9) Uani 1 1 d . . . C08 C 0.32264(12) 0.1239(3) 0.82439(19) 0.0698(6) Uani 1 1 d . . . C09 C 0.28883(13) 0.1093(3) 0.7355(2) 0.0693(7) Uani 1 1 d . . . C10 C 0.30794(12) 0.2066(3) 0.6550(2) 0.0666(6) Uani 1 1 d . . . C11 C 0.3002(3) 0.0180(6) 0.9133(3) 0.1064(11) Uani 1 1 d . . . O01 O 0.37867(9) 0.4179(3) 0.57607(12) 0.0865(6) Uani 1 1 d . . . S01 S 0.52427(4) 0.77059(9) 0.55028(6) 0.0897(3) Uani 1 1 d . . . H03 H 0.3662(18) 0.738(4) 0.684(3) 0.127(11) Uiso 1 1 d . . . H04 H 0.4583(16) 0.938(5) 0.654(2) 0.107(11) Uiso 1 1 d . . . H06 H 0.4336(15) 0.426(4) 0.7545(19) 0.089(8) Uiso 1 1 d . . . H07 H 0.3987(15) 0.248(4) 0.884(3) 0.107(10) Uiso 1 1 d . . . H09 H 0.2503(16) 0.033(4) 0.731(2) 0.105(9) Uiso 1 1 d . . . H10 H 0.2863(12) 0.205(3) 0.597(2) 0.077(7) Uiso 1 1 d . . . H11A H 0.251(2) 0.038(5) 0.931(3) 0.143(15) Uiso 1 1 d . . . H11B H 0.319(2) 0.066(5) 0.971(3) 0.142(15) Uiso 1 1 d . . . H11C H 0.310(2) -0.095(7) 0.896(4) 0.19(2) 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 C01 0.0582(13) 0.0658(14) 0.0672(14) 0.0222(10) 0.0020(10) 0.0055(10) C02 0.0674(14) 0.0828(16) 0.0698(15) 0.0139(13) 0.0094(12) 0.0056(13) C03 0.091(2) 0.096(2) 0.099(2) 0.0062(17) 0.0209(17) 0.0088(18) C04 0.135(3) 0.078(2) 0.101(2) -0.0011(19) 0.017(2) 0.016(2) C05 0.0483(11) 0.0774(15) 0.0627(14) -0.0052(11) 0.0090(10) -0.0012(10) C06 0.0577(14) 0.108(2) 0.0822(19) 0.0077(16) -0.0106(13) -0.0281(14) C07 0.0802(17) 0.107(2) 0.0736(18) 0.0091(16) -0.0185(15) -0.0213(15) C08 0.0649(13) 0.0647(14) 0.0797(16) 0.0003(12) -0.0001(12) -0.0016(11) C09 0.0635(14) 0.0601(14) 0.0844(18) -0.0091(12) 0.0028(13) -0.0096(11) C10 0.0593(13) 0.0731(15) 0.0673(16) -0.0225(13) -0.0036(11) 0.0017(11) C11 0.116(3) 0.104(3) 0.099(3) 0.025(2) 0.005(2) -0.013(2) O01 0.0707(11) 0.1185(15) 0.0702(11) 0.0064(10) 0.0068(8) -0.0234(10) S01 0.1021(6) 0.0678(4) 0.0992(6) 0.0178(3) 0.0165(4) -0.0105(3) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 C01 C02 1.366(3) . ? C01 C01 1.453(5) 5_666 ? C01 S01 1.722(3) . ? C02 O01 1.381(3) . ? C02 C03 1.407(4) . ? C03 C04 1.325(5) . ? C04 S01 1.710(4) . ? C05 C06 1.368(3) . ? C05 C10 1.377(3) . ? C05 O01 1.389(3) . ? C06 C07 1.371(4) . ? C07 C08 1.376(4) . ? C08 C09 1.368(4) . ? C08 C11 1.505(4) . ? C09 C10 1.362(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 C02 C01 C01 128.4(3) . 5_666 ? C02 C01 S01 109.23(18) . . ? C01 C01 S01 122.4(2) 5_666 . ? C01 C02 O01 121.2(2) . . ? C01 C02 C03 114.8(2) . . ? O01 C02 C03 123.8(2) . . ? C04 C03 C02 111.1(3) . . ? C03 C04 S01 113.6(3) . . ? C06 C05 C10 119.7(2) . . ? C06 C05 O01 124.5(2) . . ? C10 C05 O01 115.9(2) . . ? C05 C06 C07 118.9(2) . . ? C06 C07 C08 122.8(3) . . ? C09 C08 C07 116.6(2) . . ? C09 C08 C11 121.7(3) . . ? C07 C08 C11 121.7(3) . . ? C10 C09 C08 122.2(2) . . ? C09 C10 C05 119.9(2) . . ? C02 O01 C05 118.04(18) . . ? C04 S01 C01 91.36(17) . . ?