# Supplementary Material (ESI) for Journal of Materials Chemistry # This journal is (C) The Royal Society of Chemistry 2009 data_global _journal_name_full J.Mater.Chem. _journal_coden_Cambridge 1145 _publ_contact_author_name 'Craig MacKinnon' _publ_contact_author_email CRAIG.MACKINNON@LAKEHEADU.CA _publ_section_title ; Oligothiophenes Substituted with the Thionitrile Group: Characterization and Thin-Film Formation on Gold Substrates ; loop_ _publ_author_name 'Craig MacKinnon' 'Abdeljalil Assoud' 'Aicheng Chen' "Danielle N. D'Aleo" 'Marissa Hudolin' 'Hilary A. Jenkins' ; I.S.Morgan ; # Attachment 'BrT2SCN_centred.cif' data_cdm-7_0ma _database_code_depnum_ccdc_archive 'CCDC 729271' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C9 H4 Br N S3' _chemical_formula_weight 302.22 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' N N 0.0061 0.0033 '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' Br Br -0.2901 2.4595 '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 18.9434(15) _cell_length_b 4.6452(4) _cell_length_c 25.872(3) _cell_angle_alpha 90.00 _cell_angle_beta 110.3690(10) _cell_angle_gamma 90.00 _cell_volume 2134.3(3) _cell_formula_units_Z 8 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description cube _exptl_crystal_colour colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.881 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1184 _exptl_absorpt_coefficient_mu 4.394 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.4736 _exptl_absorpt_correction_T_max 0.7785 _exptl_absorpt_process_details 'APEX II' _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12838 _diffrn_reflns_av_R_equivalents 0.0265 _diffrn_reflns_av_sigmaI/netI 0.0282 _diffrn_reflns_limit_h_min -26 _diffrn_reflns_limit_h_max 26 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -36 _diffrn_reflns_limit_l_max 36 _diffrn_reflns_theta_min 3.28 _diffrn_reflns_theta_max 30.00 _reflns_number_total 3122 _reflns_number_gt 2775 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0236P)^2^+0.9094P] 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 none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3122 _refine_ls_number_parameters 127 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0262 _refine_ls_R_factor_gt 0.0217 _refine_ls_wR_factor_ref 0.0584 _refine_ls_wR_factor_gt 0.0565 _refine_ls_goodness_of_fit_ref 1.063 _refine_ls_restrained_S_all 1.063 _refine_ls_shift/su_max 0.002 _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 Br Br 0.618407(9) 0.88049(4) 0.539944(7) 0.03730(6) Uani 1 1 d . . . S1 S 0.67330(2) 0.50635(9) 0.461424(16) 0.03157(9) Uani 1 1 d . . . S2 S 0.57744(2) -0.05533(10) 0.318410(17) 0.03744(10) Uani 1 1 d . . . S3 S 0.63320(4) -0.46190(10) 0.24952(2) 0.05378(14) Uani 1 1 d . . . C8 C 0.59980(8) 0.6511(3) 0.47716(6) 0.0295(3) Uani 1 1 d . . . C4 C 0.63951(9) 0.1367(3) 0.37217(6) 0.0295(3) Uani 1 1 d . . . C6 C 0.53834(9) 0.3716(4) 0.40190(7) 0.0348(3) Uani 1 1 d . . . H6A H 0.4972 0.2892 0.3749 0.042 Uiso 1 1 calc R . . C5 C 0.61137(8) 0.3190(3) 0.40628(6) 0.0284(3) Uani 1 1 d . . . C3 C 0.71260(10) 0.0828(4) 0.37678(7) 0.0374(3) Uani 1 1 d . . . H3A H 0.7539 0.1682 0.4032 0.045 Uiso 1 1 calc R . . C2 C 0.71881(11) -0.1158(4) 0.33723(7) 0.0404(4) Uani 1 1 d . . . H2A H 0.7644 -0.1768 0.3350 0.049 Uiso 1 1 calc R . . C1 C 0.65054(10) -0.2075(4) 0.30279(6) 0.0378(3) Uani 1 1 d . . . C7 C 0.53148(9) 0.5631(4) 0.44239(6) 0.0339(3) Uani 1 1 d . . . H7A H 0.4858 0.6215 0.4449 0.041 Uiso 1 1 calc R . . N N 0.62788(11) -0.0950(4) 0.16054(7) 0.0578(5) Uani 1 1 d . . . C9 C 0.62989(9) -0.2385(4) 0.19668(7) 0.0400(4) Uani 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 Br 0.03780(9) 0.03740(10) 0.04095(10) -0.00782(6) 0.01905(7) -0.00018(6) S1 0.02750(16) 0.0343(2) 0.03582(18) -0.00271(15) 0.01471(14) 0.00105(14) S2 0.0443(2) 0.0378(2) 0.03288(19) -0.00225(15) 0.01679(16) -0.00360(16) S3 0.1025(4) 0.0289(2) 0.0414(2) -0.00123(17) 0.0395(3) -0.0032(2) C8 0.0327(7) 0.0272(7) 0.0331(7) 0.0028(5) 0.0173(6) 0.0041(5) C4 0.0371(7) 0.0279(7) 0.0269(6) 0.0048(5) 0.0154(6) 0.0020(5) C6 0.0304(7) 0.0419(9) 0.0319(7) 0.0007(6) 0.0104(6) 0.0021(6) C5 0.0332(7) 0.0272(7) 0.0264(6) 0.0043(5) 0.0124(5) 0.0019(5) C3 0.0385(8) 0.0403(9) 0.0370(8) -0.0007(6) 0.0177(7) 0.0048(7) C2 0.0496(9) 0.0389(9) 0.0406(8) 0.0058(7) 0.0255(8) 0.0118(7) C1 0.0611(10) 0.0272(7) 0.0326(7) 0.0034(6) 0.0258(7) 0.0044(7) C7 0.0287(7) 0.0396(8) 0.0360(7) 0.0023(6) 0.0146(6) 0.0060(6) N 0.0588(10) 0.0768(13) 0.0384(8) 0.0126(8) 0.0177(8) -0.0067(9) C9 0.0451(9) 0.0458(10) 0.0328(8) -0.0018(7) 0.0184(7) -0.0030(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 Br C8 1.8706(15) . ? S1 C8 1.7181(15) . ? S1 C5 1.7334(15) . ? S2 C1 1.7234(17) . ? S2 C4 1.7246(16) . ? S3 C9 1.7001(18) . ? S3 C1 1.7577(17) . ? C8 C7 1.357(2) . ? C4 C3 1.371(2) . ? C4 C5 1.452(2) . ? C6 C5 1.370(2) . ? C6 C7 1.414(2) . ? C3 C2 1.413(2) . ? C2 C1 1.359(3) . ? N C9 1.138(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 C8 S1 C5 91.11(7) . . ? C1 S2 C4 91.33(8) . . ? C9 S3 C1 99.47(8) . . ? C7 C8 S1 112.93(12) . . ? C7 C8 Br 126.54(12) . . ? S1 C8 Br 120.36(9) . . ? C3 C4 C5 128.83(15) . . ? C3 C4 S2 111.12(12) . . ? C5 C4 S2 120.03(12) . . ? C5 C6 C7 113.67(14) . . ? C6 C5 C4 128.88(14) . . ? C6 C5 S1 110.68(11) . . ? C4 C5 S1 120.44(12) . . ? C4 C3 C2 113.10(16) . . ? C1 C2 C3 112.30(15) . . ? C2 C1 S2 112.14(12) . . ? C2 C1 S3 126.91(13) . . ? S2 C1 S3 120.89(11) . . ? C8 C7 C6 111.61(14) . . ? N C9 S3 178.20(19) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 30.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.439 _refine_diff_density_min -0.251 _refine_diff_density_rms 0.056 # Attachment 'T2SCN2.cif' data_cm0505m _database_code_depnum_ccdc_archive 'CCDC 729272' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C10 H4 N2 S4' _chemical_formula_weight 280.39 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' N N 0.0061 0.0033 '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 P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 3.9636(12) _cell_length_b 16.715(5) _cell_length_c 8.572(3) _cell_angle_alpha 90.00 _cell_angle_beta 92.157(5) _cell_angle_gamma 90.00 _cell_volume 567.5(3) _cell_formula_units_Z 2 _cell_measurement_temperature 223(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max .3 _exptl_crystal_size_mid .3 _exptl_crystal_size_min .3 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.641 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 284 _exptl_absorpt_coefficient_mu 0.805 _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 223(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 '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_% ? _diffrn_reflns_number 4051 _diffrn_reflns_av_R_equivalents 0.0553 _diffrn_reflns_av_sigmaI/netI 0.0330 _diffrn_reflns_limit_h_min -4 _diffrn_reflns_limit_h_max 4 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.44 _diffrn_reflns_theta_max 24.99 _reflns_number_total 997 _reflns_number_gt 908 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0753P)^2^+0.3772P] 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 none _refine_ls_extinction_coef ? _refine_ls_number_reflns 997 _refine_ls_number_parameters 73 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0682 _refine_ls_R_factor_gt 0.0651 _refine_ls_wR_factor_ref 0.1268 _refine_ls_wR_factor_gt 0.1256 _refine_ls_goodness_of_fit_ref 1.156 _refine_ls_restrained_S_all 1.156 _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 S1 S 0.27665(19) 0.61766(4) 0.54014(9) 0.0285(3) Uani 1 1 d . . . S2 S 0.1641(2) 0.72595(5) 0.82058(11) 0.0373(3) Uani 1 1 d . . . N1 N 0.4418(8) 0.8522(2) 0.6445(4) 0.0427(8) Uani 1 1 d . . . C5 C 0.3358(8) 0.7995(2) 0.7133(4) 0.0304(8) Uani 1 1 d . . . C1 C 0.4739(7) 0.52579(17) 0.5668(4) 0.0248(7) Uani 1 1 d . . . C2 C 0.5702(8) 0.51458(19) 0.7193(4) 0.0320(8) Uani 1 1 d . . . H2A H 0.6778 0.4678 0.7565 0.038 Uiso 1 1 calc R . . C3 C 0.4930(8) 0.5800(2) 0.8164(4) 0.0319(7) Uani 1 1 d . . . H3A H 0.5443 0.5815 0.9243 0.038 Uiso 1 1 calc R . . C4 C 0.3359(8) 0.6405(2) 0.7359(4) 0.0288(7) Uani 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 S1 0.0361(5) 0.0147(5) 0.0345(5) 0.0004(3) -0.0002(3) 0.0036(3) S2 0.0496(6) 0.0173(5) 0.0459(6) -0.0026(4) 0.0156(4) 0.0009(4) N1 0.062(2) 0.0233(16) 0.0424(18) 0.0008(15) -0.0009(14) -0.0022(15) C5 0.0399(18) 0.0187(17) 0.0322(17) -0.0071(15) -0.0026(13) 0.0026(14) C1 0.0283(14) 0.0111(14) 0.0349(16) 0.0028(13) 0.0009(12) -0.0024(12) C2 0.0408(17) 0.0170(16) 0.0378(17) 0.0032(14) -0.0024(13) 0.0031(14) C3 0.0447(18) 0.0190(16) 0.0318(17) -0.0005(15) -0.0009(13) -0.0006(15) C4 0.0347(16) 0.0142(15) 0.0379(17) -0.0026(14) 0.0058(12) -0.0029(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 S1 C4 1.728(3) . ? S1 C1 1.734(3) . ? S2 C5 1.693(4) . ? S2 C4 1.752(3) . ? N1 C5 1.149(5) . ? C1 C2 1.360(5) . ? C1 C1 1.455(6) 3_666 ? C2 C3 1.415(5) . ? C2 H2A 0.9400 . ? C3 C4 1.361(5) . ? C3 H3A 0.9400 . ? 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 C4 S1 C1 91.32(15) . . ? C5 S2 C4 101.32(16) . . ? N1 C5 S2 176.3(3) . . ? C2 C1 C1 129.2(4) . 3_666 ? C2 C1 S1 110.9(2) . . ? C1 C1 S1 119.8(3) 3_666 . ? C1 C2 C3 113.6(3) . . ? C1 C2 H2A 123.2 . . ? C3 C2 H2A 123.2 . . ? C4 C3 C2 112.3(3) . . ? C4 C3 H3A 123.8 . . ? C2 C3 H3A 123.8 . . ? C3 C4 S1 111.8(3) . . ? C3 C4 S2 124.9(3) . . ? S1 C4 S2 122.8(2) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.539 _refine_diff_density_min -0.479 _refine_diff_density_rms 0.098