# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2012 data_global _journal_coden_Cambridge 182 _journal_volume ? _journal_page_first ? _journal_year ? loop_ _publ_author_name 'Chiu, Shi-Wen' 'Lin, Li-Yen' 'Lin, Hao-Wu' 'Liu, Yi-Hung' 'Huang, Zheng-Yu' 'Lin, Yu-Ting' 'Lin, Francis' 'Chen, Yi-Hong' 'Wong, Ken-Tsung' _publ_contact_author_name 'Dr Ken-Tsung Wong' _publ_contact_author_email kenwong@ntu.edu.tw _publ_section_title ; A donor-acceptor-acceptor molecule for vacuum-processed organic solar cells with a power conversion efficiency of 6.4% ; # Attachment '- ic14708.cif' data_ic14708 _database_code_depnum_ccdc_archive 'CCDC 848943' #TrackingRef '- ic14708.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C60 H50 N2 O S' _chemical_formula_weight 847.08 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.9834(3) _cell_length_b 10.1056(4) _cell_length_c 14.4674(5) _cell_angle_alpha 80.452(3) _cell_angle_beta 79.680(3) _cell_angle_gamma 80.471(3) _cell_volume 1121.24(7) _cell_formula_units_Z 2 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 6864 _cell_measurement_theta_min 3.1333 _cell_measurement_theta_max 76.9494 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.509 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 896 _exptl_absorpt_coefficient_mu 1.970 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.70363 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) (compiled Oct 25 2010,18:11:34) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Oxford Diffraction Gemini A' _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12110 _diffrn_reflns_av_R_equivalents 0.0364 _diffrn_reflns_av_sigmaI/netI 0.0307 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 3.14 _diffrn_reflns_theta_max 67.98 _reflns_number_total 4084 _reflns_number_gt 3288 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) (compiled Oct 25 2010,18:11:34) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) (compiled Oct 25 2010,18:11:34) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) (compiled Oct 25 2010,18:11:34) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXTL _computing_publication_material 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^)+(0.1000P)^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_extinction_coef ? _refine_ls_number_reflns 4084 _refine_ls_number_parameters 289 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0609 _refine_ls_R_factor_gt 0.0486 _refine_ls_wR_factor_ref 0.1544 _refine_ls_wR_factor_gt 0.1398 _refine_ls_goodness_of_fit_ref 1.101 _refine_ls_restrained_S_all 1.101 _refine_ls_shift/su_max 0.089 _refine_ls_shift/su_mean 0.008 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 0.27249(7) 0.34082(5) 0.79220(3) 0.05597(19) Uani 1 1 d . . . N1 N 0.1951(2) 0.45956(18) 1.04668(13) 0.0587(4) Uani 1 1 d . . . N2 N 0.3448(2) 0.54186(18) 0.89396(12) 0.0583(4) Uani 1 1 d . . . N3 N 0.1891(3) 0.13985(18) 0.71769(12) 0.0614(4) Uani 1 1 d . . . N4 N 0.2205(3) 0.6743(2) 1.29683(16) 0.0806(6) Uani 1 1 d . . . N5 N 0.4335(4) 1.0444(2) 1.15969(19) 0.0888(7) Uani 1 1 d . . . C1 C 0.2161(2) 0.3424(2) 0.91382(13) 0.0515(4) Uani 1 1 d . . . C2 C 0.1299(3) 0.2351(2) 0.95517(15) 0.0583(5) Uani 1 1 d . . . H2A H 0.0886 0.2197 1.0198 0.070 Uiso 1 1 calc R . . C3 C 0.1101(3) 0.1512(2) 0.89157(15) 0.0599(5) Uani 1 1 d . . . H3A H 0.0550 0.0746 0.9094 0.072 Uiso 1 1 calc R . . C4 C 0.1813(3) 0.1944(2) 0.79865(15) 0.0544(4) Uani 1 1 d . . . C5 C 0.2801(3) 0.2015(2) 0.62980(15) 0.0602(5) Uani 1 1 d . . . C6 C 0.4384(4) 0.1361(3) 0.5936(2) 0.0804(7) Uani 1 1 d . . . H6A H 0.4848 0.0542 0.6252 0.097 Uiso 1 1 calc R . . C7 C 0.5269(4) 0.1946(3) 0.5095(2) 0.0900(8) Uani 1 1 d . . . H7A H 0.6329 0.1504 0.4845 0.108 Uiso 1 1 calc R . . C8 C 0.4611(4) 0.3175(3) 0.46182(17) 0.0762(7) Uani 1 1 d . . . C9 C 0.3045(4) 0.3807(3) 0.50011(17) 0.0717(6) Uani 1 1 d . . . H9A H 0.2589 0.4637 0.4695 0.086 Uiso 1 1 calc R . . C10 C 0.2129(3) 0.3231(2) 0.58383(15) 0.0646(5) Uani 1 1 d . . . H10A H 0.1064 0.3668 0.6085 0.078 Uiso 1 1 calc R . . C11 C 0.5590(5) 0.3805(4) 0.3701(2) 0.1055(11) Uani 1 1 d . . . H11A H 0.4944 0.4648 0.3475 0.158 Uiso 1 1 calc R . . H11B H 0.5760 0.3200 0.3235 0.158 Uiso 1 1 calc R . . H11C H 0.6685 0.3965 0.3810 0.158 Uiso 1 1 calc R . . C12 C 0.1123(3) 0.0225(2) 0.71494(14) 0.0556(5) Uani 1 1 d . . . C13 C 0.1380(3) -0.0943(2) 0.77848(17) 0.0651(5) Uani 1 1 d . . . H13A H 0.2066 -0.0980 0.8247 0.078 Uiso 1 1 calc R . . C14 C 0.0616(4) -0.2057(2) 0.77344(17) 0.0698(6) Uani 1 1 d . . . H14A H 0.0790 -0.2836 0.8169 0.084 Uiso 1 1 calc R . . C15 C -0.0397(4) -0.2033(2) 0.70512(17) 0.0693(6) Uani 1 1 d . . . C16 C -0.0613(3) -0.0869(3) 0.64101(16) 0.0716(6) Uani 1 1 d . . . H16A H -0.1271 -0.0843 0.5936 0.086 Uiso 1 1 calc R . . C17 C 0.0122(3) 0.0260(2) 0.64539(15) 0.0668(6) Uani 1 1 d . . . H17A H -0.0053 0.1038 0.6019 0.080 Uiso 1 1 calc R . . C18 C -0.1219(6) -0.3262(4) 0.7012(2) 0.1129(13) Uani 1 1 d . . . H18A H -0.1885 -0.3073 0.6503 0.169 Uiso 1 1 calc R . . H18B H -0.1954 -0.3478 0.7601 0.169 Uiso 1 1 calc R . . H18C H -0.0339 -0.4017 0.6906 0.169 Uiso 1 1 calc R . . C19 C 0.2533(2) 0.4522(2) 0.95346(14) 0.0528(4) Uani 1 1 d . . . C20 C 0.2284(3) 0.5648(2) 1.07960(15) 0.0602(5) Uani 1 1 d . . . H20A H 0.1880 0.5734 1.1430 0.072 Uiso 1 1 calc R . . C21 C 0.3211(3) 0.6647(2) 1.02474(15) 0.0544(4) Uani 1 1 d . . . C22 C 0.3760(3) 0.6448(2) 0.93002(15) 0.0575(5) Uani 1 1 d . . . H22A H 0.4381 0.7080 0.8903 0.069 Uiso 1 1 calc R . . C23 C 0.3612(3) 0.7825(2) 1.05549(16) 0.0588(5) Uani 1 1 d . . . H23A H 0.4111 0.8432 1.0071 0.071 Uiso 1 1 calc R . . C24 C 0.3387(3) 0.8196(2) 1.14287(16) 0.0578(5) Uani 1 1 d . . . C25 C 0.2718(3) 0.7389(2) 1.22886(17) 0.0625(5) Uani 1 1 d . . . C26 C 0.3911(3) 0.9447(2) 1.15360(18) 0.0678(6) 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 0.0619(3) 0.0579(3) 0.0475(3) -0.00170(19) -0.0010(2) -0.0204(2) N1 0.0639(10) 0.0574(9) 0.0532(9) -0.0048(7) 0.0015(7) -0.0186(8) N2 0.0635(10) 0.0623(10) 0.0482(9) 0.0002(7) -0.0046(7) -0.0183(8) N3 0.0777(11) 0.0564(9) 0.0496(9) -0.0036(7) 0.0015(8) -0.0241(8) N4 0.0906(15) 0.0820(14) 0.0664(13) -0.0070(10) 0.0078(11) -0.0292(12) N5 0.1026(17) 0.0777(14) 0.0917(16) -0.0132(12) -0.0035(13) -0.0403(13) C1 0.0489(10) 0.0570(10) 0.0456(9) -0.0038(8) -0.0015(7) -0.0082(8) C2 0.0603(12) 0.0618(11) 0.0487(10) -0.0051(8) 0.0033(8) -0.0126(9) C3 0.0659(12) 0.0569(11) 0.0541(11) -0.0034(8) 0.0041(9) -0.0195(9) C4 0.0544(10) 0.0537(10) 0.0535(11) -0.0045(8) -0.0031(8) -0.0119(8) C5 0.0717(13) 0.0601(11) 0.0496(11) -0.0078(9) 0.0026(9) -0.0243(10) C6 0.0845(17) 0.0723(15) 0.0752(16) -0.0049(12) 0.0061(13) -0.0098(13) C7 0.0797(17) 0.097(2) 0.0836(18) -0.0170(15) 0.0220(14) -0.0171(15) C8 0.0887(17) 0.0887(17) 0.0548(12) -0.0130(11) 0.0083(11) -0.0410(14) C9 0.0944(17) 0.0688(13) 0.0527(12) -0.0018(10) -0.0052(11) -0.0276(12) C10 0.0731(14) 0.0656(12) 0.0523(11) -0.0051(9) 0.0016(10) -0.0168(10) C11 0.116(3) 0.128(3) 0.0703(17) -0.0052(17) 0.0220(17) -0.059(2) C12 0.0620(11) 0.0531(10) 0.0499(10) -0.0048(8) -0.0008(8) -0.0139(8) C13 0.0772(14) 0.0588(11) 0.0617(12) -0.0008(9) -0.0191(10) -0.0147(10) C14 0.0957(17) 0.0538(11) 0.0605(13) 0.0009(9) -0.0148(12) -0.0182(11) C15 0.0892(16) 0.0658(13) 0.0568(12) -0.0072(10) -0.0055(11) -0.0305(12) C16 0.0873(16) 0.0796(15) 0.0541(12) -0.0065(10) -0.0169(11) -0.0258(12) C17 0.0885(16) 0.0617(12) 0.0492(11) 0.0021(9) -0.0109(10) -0.0177(11) C18 0.171(4) 0.100(2) 0.089(2) -0.0006(17) -0.033(2) -0.078(2) C19 0.0478(10) 0.0566(10) 0.0509(10) -0.0008(8) -0.0054(8) -0.0082(8) C20 0.0668(12) 0.0618(11) 0.0508(11) -0.0077(9) 0.0011(9) -0.0175(9) C21 0.0513(10) 0.0554(10) 0.0543(11) -0.0010(8) -0.0061(8) -0.0098(8) C22 0.0573(11) 0.0596(11) 0.0533(11) 0.0044(8) -0.0063(8) -0.0167(9) C23 0.0564(11) 0.0565(11) 0.0615(12) 0.0022(9) -0.0066(9) -0.0157(9) C24 0.0531(11) 0.0569(11) 0.0633(12) -0.0060(9) -0.0045(9) -0.0148(8) C25 0.0619(12) 0.0624(12) 0.0639(13) -0.0128(10) -0.0016(10) -0.0152(10) C26 0.0689(13) 0.0688(14) 0.0673(13) -0.0074(10) -0.0059(10) -0.0221(11) _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 1.736(2) . ? S1 C1 1.7385(19) . ? N1 C20 1.317(3) . ? N1 C19 1.356(3) . ? N2 C22 1.315(3) . ? N2 C19 1.353(3) . ? N3 C4 1.363(3) . ? N3 C12 1.431(3) . ? N3 C5 1.445(3) . ? N4 C25 1.137(3) . ? N5 C26 1.136(3) . ? C1 C2 1.376(3) . ? C1 C19 1.425(3) . ? C2 C3 1.395(3) . ? C3 C4 1.391(3) . ? C5 C10 1.371(3) . ? C5 C6 1.382(4) . ? C6 C7 1.386(4) . ? C7 C8 1.387(4) . ? C8 C9 1.372(4) . ? C8 C11 1.513(3) . ? C9 C10 1.390(3) . ? C12 C17 1.385(3) . ? C12 C13 1.381(3) . ? C13 C14 1.384(3) . ? C14 C15 1.380(3) . ? C15 C16 1.379(3) . ? C15 C18 1.511(3) . ? C16 C17 1.382(3) . ? C20 C21 1.403(3) . ? C21 C22 1.399(3) . ? C21 C23 1.439(3) . ? C23 C24 1.351(3) . ? C24 C26 1.436(3) . ? C24 C25 1.438(3) . ? 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 91.75(9) . . ? C20 N1 C19 116.18(18) . . ? C22 N2 C19 116.67(18) . . ? C4 N3 C12 123.21(17) . . ? C4 N3 C5 119.17(17) . . ? C12 N3 C5 117.63(17) . . ? C2 C1 C19 130.65(19) . . ? C2 C1 S1 110.66(15) . . ? C19 C1 S1 118.56(15) . . ? C1 C2 C3 114.00(19) . . ? C2 C3 C4 112.83(19) . . ? N3 C4 C3 130.30(19) . . ? N3 C4 S1 118.94(15) . . ? C3 C4 S1 110.76(16) . . ? C10 C5 C6 120.5(2) . . ? C10 C5 N3 121.0(2) . . ? C6 C5 N3 118.5(2) . . ? C7 C6 C5 118.9(3) . . ? C6 C7 C8 121.5(3) . . ? C9 C8 C7 118.2(2) . . ? C9 C8 C11 120.8(3) . . ? C7 C8 C11 121.1(3) . . ? C8 C9 C10 121.2(2) . . ? C5 C10 C9 119.7(2) . . ? C17 C12 C13 119.39(19) . . ? C17 C12 N3 118.81(18) . . ? C13 C12 N3 121.79(19) . . ? C14 C13 C12 120.1(2) . . ? C13 C14 C15 121.2(2) . . ? C16 C15 C14 118.0(2) . . ? C16 C15 C18 121.8(2) . . ? C14 C15 C18 120.2(2) . . ? C15 C16 C17 121.7(2) . . ? C12 C17 C16 119.6(2) . . ? N1 C19 N2 125.06(19) . . ? N1 C19 C1 118.30(18) . . ? N2 C19 C1 116.64(18) . . ? N1 C20 C21 124.0(2) . . ? C22 C21 C20 114.40(19) . . ? C22 C21 C23 118.53(19) . . ? C20 C21 C23 127.1(2) . . ? N2 C22 C21 123.72(19) . . ? C24 C23 C21 130.8(2) . . ? C23 C24 C26 119.3(2) . . ? C23 C24 C25 124.5(2) . . ? C26 C24 C25 116.2(2) . . ? N4 C25 C24 179.3(3) . . ? N5 C26 C24 178.3(3) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 67.98 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.228 _refine_diff_density_min -0.226 _refine_diff_density_rms 0.046