# Supplementary Material (ESI) for Journal of Materials Chemistry # This journal is (C) The Royal Society of Chemistry 2010 data_global _journal_name_full J.Mater.Chem. _journal_coden_Cambridge 1145 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Richard McCullough' _publ_contact_author_email rm5g@andrew.cmu.edu _publ_section_title ; Mixed Selenium-Sulfur Fused Ring Systems as Building Blocks for Novel Polymers Used in Field Effect Transistors ; _publ_contact_author ; Richard D. McCullough ; loop_ _publ_author_name 'Sarada Mishra' 'Anna Javier' 'Junying Liu.' 'John Belot' 'Itaru Osaka' 'Richard McCullough' # Attachment '- k59eb.txt' data_k59e _database_code_depnum_ccdc_archive 'CCDC 763008' #TrackingRef '- k59eb.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; selenolo[3,2-b]thiophene ; _chemical_name_common selenolo(3,2-b)thiophene _chemical_melting_point 359 _chemical_formula_moiety ? _chemical_formula_sum 'C6 H4 S Se' _chemical_formula_weight 187.11 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' Se Se -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pbca loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 9.9543(7) _cell_length_b 5.9678(4) _cell_length_c 10.1404(7) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 602.39(7) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 3921 _cell_measurement_theta_min 3.41 _cell_measurement_theta_max 30.49 _exptl_crystal_description 'Nearly equidimensional' _exptl_crystal_colour Pale _exptl_crystal_size_max 0.44 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.38 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.063 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 360 _exptl_absorpt_coefficient_mu 6.450 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.665 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART APEX CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0.00 _diffrn_reflns_number 6449 _diffrn_reflns_av_R_equivalents 0.0504 _diffrn_reflns_av_sigmaI/netI 0.0238 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 4.02 _diffrn_reflns_theta_max 30.52 _reflns_number_total 916 _reflns_number_gt 822 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0323P)^2^+0.2394P] 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 SHELXL _refine_ls_extinction_coef 0.0183(16) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 916 _refine_ls_number_parameters 46 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0224 _refine_ls_R_factor_gt 0.0201 _refine_ls_wR_factor_ref 0.0596 _refine_ls_wR_factor_gt 0.0585 _refine_ls_goodness_of_fit_ref 1.058 _refine_ls_restrained_S_all 1.058 _refine_ls_shift/su_max 0.000 _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 Se Se 0.110755(18) 0.25974(3) 0.39519(2) 0.01385(11) Uani 0.50 1 d P . . S S 0.110755(18) 0.25974(3) 0.39519(2) 0.01385(11) Uani 0.50 1 d P . . C1 C 0.06547(11) 0.03562(19) 0.51023(11) 0.0123(2) Uani 1 1 d . . . C2 C -0.05689(14) 0.2324(2) 0.32544(14) 0.0142(3) Uani 1 1 d . . . H2 H -0.0812(18) 0.320(3) 0.253(2) 0.017(4) Uiso 1 1 d . . . C3 C -0.13485(13) 0.0752(2) 0.38536(12) 0.0136(3) Uani 1 1 d . . . H3 H -0.2250(19) 0.055(3) 0.3582(17) 0.021(4) 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 Se 0.01223(15) 0.01505(15) 0.01427(16) 0.00070(6) -0.00006(6) 0.00007(5) S 0.01223(15) 0.01505(15) 0.01427(16) 0.00070(6) -0.00006(6) 0.00007(5) C1 0.0122(5) 0.0111(5) 0.0135(5) -0.0004(4) 0.0021(4) 0.0002(4) C2 0.0144(6) 0.0145(6) 0.0138(5) 0.0003(4) -0.0005(5) 0.0019(4) C3 0.0117(5) 0.0141(6) 0.0149(5) -0.0015(4) 0.0000(4) 0.0011(4) _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 Se C2 1.8197(14) . ? Se C1 1.8311(12) . ? C1 C1 1.387(2) 5_556 ? C1 C3 1.4267(17) 5_556 ? C2 C3 1.3608(18) . ? C2 H2 0.933(19) . ? C3 C1 1.4267(17) 5_556 ? C3 H3 0.946(19) . ? 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 C2 Se C1 87.50(6) . . ? C1 C1 C3 115.08(13) 5_556 5_556 ? C1 C1 Se 111.10(12) 5_556 . ? C3 C1 Se 133.81(9) 5_556 . ? C3 C2 Se 114.28(10) . . ? C3 C2 H2 126.1(11) . . ? Se C2 H2 119.6(11) . . ? C2 C3 C1 112.02(12) . 5_556 ? C2 C3 H3 119.8(12) . . ? C1 C3 H3 128.1(12) 5_556 . ? 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 C2 Se C1 C1 -0.93(12) . . . 5_556 ? C2 Se C1 C3 -179.96(13) . . . 5_556 ? C1 Se C2 C3 0.94(11) . . . . ? Se C2 C3 C1 -0.70(15) . . . 5_556 ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 30.52 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.405 _refine_diff_density_min -0.414 _refine_diff_density_rms 0.084