Composed of Thiophene, Pyrrole and Methylthio

upporting Information Biradical Character of Linear π-conjugated Oligomer Dications Composed of Thiophene, Pyrrole and Methylthio End nd-capping Units Tohru Nishinaga,* Masaki Tateno, Mika Fujii, Wataru Fujita, Masayoshi Takase and Masahiko Iyoda Department of Chemistry, Graduate chool of cience and Engineering, Tokyo Metropolitan University, Hachioji, Tokyo 192-0397, Japan. Fax: (+81)42-677-2525; Tel: (+81)42-677-2546; E-mail: nishinaga-tohru@tmu.ac.jp General 1 H and 13 C NMR spectra were recorded on JEOL JNM-270, LA-400 or L-500 instruments. Chemical shifts are reported in ppm with reference to tetramethylsilane. Preparative gel-permeation chromatography (GPC) was performed with a JAI LC-08 chromatograph equipped with JAIGEL 1H and 2H columns. Electronic spectra were recorded on a HIMADZU UV-Vis-NIR scanning spectrophotometer (Model UV-3101-PC). ER spectra were recorded on JEOL JE-RE3X instruments. Magnetic measurements of Me-9TPC 9TPC12 2+ (bcl6 )2 were carried out on a Quantum Design MPM-XL QUID magnetometer on powder samples in the temperature range from 2 K to 300 K under 5000 Oe. The molar susceptibility, χ M, was obtained from the raw magnetic data, subtracting a diamagnetic contribution of the sample in it. Elemental analyses were performed at the microanalysis laboratory of Tokyo Metropolitan University. Commercially available reagents were used as received. olvents were distilled from relevant drying agents prior to use. 1,4-Bis(2 -thienyl)-1,4-butanedione, 1 2,5-bis(2 -thienyl) -N-alkyl-pyrrole (1), 2 6TP-C 12, 2 5,5'-Dibromo-2,2'-bithiophene 3 and 5,5 -Dibromo-2,2 :5,2 -terthiophene 4 were prepared according to the literature procedures. Computational methods DFT calculations were performed with the Gaussian 03 program. 5 All geometry optimizations were carried out at the B3LYP/6 31G(d) basis set. For ntp-c 2+ 1, the total energy of the optimized structures with C 2 symmetry was found to be lower than that with C i or C s symmetry, and therefore C 2 symmetry was also applied for the geometry optimizations of Me-nTP-C 2+ 1. inglet biradical character was estimated with the symmetry-broken UB3LYP/6 31G(d) method with a geometry optimization and the biradical index was determined on the basis of the LUMO occupation number in natural orbital analysis. Excitation energy was computed using time-dependent density functional theory (TD B3LYP) with 6-31G(d) basis set in the B3LYP optimized geometry. 1

ynthesis ynthesis of 2. To a THF solution (10 ml) of 1 (m = 12) (754 mg, 1.89 mmol) and TMEDA (0.30 ml, 2.0 mmol) was added n-butyllithium (1,6 M, 2.1 mmol) in hexane at 78 C under N 2. After stirring for 30 min at 78 C and ca. 5 min at rt, dimethyldisulfide (0.20 ml, 2.3 mmol) was added to the reaction mixture at 78 C. Then, after additional stirring for 10 min at 78 C, the reaction mixture was allowed to warm to rt. A standard workup using NH 4 Cl aq and dichloromethane and column chromatography (io 2 / hexane) gave 2 (m = 12) (533 mg, 1.20 mmol, 63 %) as pale yellow oil; 1 H NMR(CDCl 3 ) δ 7.31(dd, 1H), 7.10 7.01(m, 3H), 6.90(d, 1H), 6.31(dd, 2H), 4.11(t, 2H), 2.52(s, 3H), 1.52 1.50(m, 2H), 1.40 1.10(m, 18H), 0.88(t, 3H); 13 C NMR(CDCl 3 ) δ 137.25, 136.35, 134.69, 131.10, 128.42, 127.93, 127.12, 125.83, 125.74, 125.15, 110.73, 110.68, 45.22, 31.98, 31.21, 29.68, 29.68, 29.56, 29.42, 29.40, 28.97, 26.43, 22.77, 22.21, 14.23. Anal. Calcd for C 25 H 35 N 3 : C, 67.36; H, 7.91; N, 3.14;, 21.58, Found: C, 67.32; H, 7.95; N, 3.19. 1 H-NMR spectrum of 2 (m = 12) N C m H 2m+1 2 m = 12 Me 2

13 C-NMR spectrum of 2 (m = 12) N C m H 2m+1 2 m = 12 Me ame procedure was applied for 2 (m = 6): 71% yield; colorless oil; 1 H NMR(CDCl 3 ) δ 7.32 (dd, 1H, J = 5.2, 1.2 Hz), 7.09-7.05 (m, 2H), 7.04 (d, 1H, J = 3.7 Hz), 6.90 (d, 1H, J = 3.7 Hz), 6.32-6.30 (m, 2H), 4.11 (t, 2H, J = 7.9 Hz), 2.53 (s, 3H), 1.60-1.52 (m, 2H), 1.20-1.10 (m, 6H), 0.81 (t, 3H, J = 7.2 Hz); 13 C NMR δ 137.1, 136.2, 134.6, 131.0, 128.3, 127.8, 127.0, 125.62, 125.56, 125.0, 110.7, 110.6, 45.1, 31.1, 31.0, 26.0, 22.4, 22.0, 13.9. Anal. Calcd for C19H23N3: N, 3.87; C, 63.11; H, 6.41. Found: N, 3.80; C, 63.43; H, 6.44. 3

1 H-NMR spectrum of 2 (m = 6) N C m H 2m+1 2 m = 6 Me 13 C-NMR spectrum of 2 (m = 6) N C m H 2m+1 2 m = 6 Me 4

ynthesis of Me-6TP 6TP-C6. To a THF solution (30 ml) of 2 (m = 6) (1.20 g, 3.33 mmol) and TMEDA (0.60 ml, 4.0 mmol) was added n-butyllithium (1.6 M, 4.0 mmol) in hexane at 78 C under N 2. After stirring for 30 min at 78 C and 5 min at rt, CuCl 2 (1.38 g, 10.3 mmol) was added to the reaction mixture at 78 C, stirred overnight at rt. A standard workup using NH 4 Cl aq and dichloromethane and column chromatography (io 2 deactivated with 10% water / at dark / hexanedichloromethane) gave Me-6TP-C 6 (820 mg, 1.14 mmol, 68%) as yellow solid: 1 HNMR (CDCl 3 ) δ 7.14 (d, 2H, J = 3.7 Hz), 7.05 (d, 2H, J = 3.7 Hz), 6.97 (d, 2H, J = 3.7 Hz), 6.91 (d, 2H, J = 3.7 Hz), 6.36 (d, 2H, J = 3.7 Hz), 6.32 (d, 2H, J = 3.7 Hz), 4.17 (t, 4H, J = 7.8 Hz), 2.53 (s, 6H), 1.64-1.58 (m, 4H), 1.23-1.14 (m, 12H), 0.82 (t, 6H, J = 7.0 Hz); 13 C-NMR (CDCl3) δ 137.0, 136.52, 136.45, 133.6, 131.1, 128.4, 128.2, 126.0, 125.9, 123.6, 111.0, 110.9, 45.4, 31.20, 31.17, 26.2, 22.5, 22.2, 14.1; M(EI) m/z 720 [M + ]. Anal. Calcd for C38H44N26: N, 3.88; C, 63.29; H, 6.15. Found: N, 3.89; C, 63.37; H, 6.16. 1 H-NMR spectrum of Me-6TP 6TP-C6 C 6 H 13 H 3 C N N CH 3 C 6 H 13 5

13 C-NMR spectrum of Me-6TP 6TP-C6 C 6 H 13 H 3 C N N CH 3 C 6 H 13 ynthesis of Me-nTP-C 12. To a THF solution (18 ml) of 2 (m = 12) (570 mg, 1.28 mmol) and TMEDA (0.19 ml, 1.27 mmol) was added n-butyllithium (1.6 M, 1.4 mmol) in hexane at 78 C under N 2. After stirring for 30 min at 78 C and 5 min at 0 C, B(O i Pr) 3 (0.35 ml, 1.5 mmol) was added to the reaction mixture at 78 C. After stirring for 90 min, pinacol (315 mg, 1.67 mmol) was added and stirred overnight at rt. A standard workup using NH 4 Cl aq and dichloromethane and column chromatography (Al 2 O 3 deactivated with 10% water / hexane-benzene) gave the boronic acid pinacol ester as pale yellow oil; 1 HNMR (CDCl 3 ): δ 7.59 (d, 1H), 7.12 (d, 1H), 7.03(d, 1H), 6.89(d, 1H), 6.36(d, 1H),6.30 (d, 1H), 4.16 (t, 3H), 2.52 (s, 3H), 1.36 (s, 12H), 1.3 1.1 (m, 20H), 0.88 (t, 3H). To a mixture of the boronic acid pinacol ester prepared above (1.06 g, 1.87 mmol), 2,5-dibromo thiophene (215 mg, 0.89 mmol) and Pd (PPh 3 ) 4 (96 mg, 0.083 mmol) in a tube equipped with a stop cock were added toluene (40 ml) and 2N K2CO3aq (17 ml) under N2. After heating at 110 C for 24 h, a standard workup using NH 4 Cl aq and dichloromethane, separation with preparative GPC and column chromatography (Al 2 O 3 deactivated with 10% water / hexane-benzene) and recrystallization from a mixture of dichloromethane and ethyl acetate gave Me-7TP-C 12 (258 mg, 0.266 mmol, 29.8%) as yellow solid: 1 HNMR (CDCl 3 ) δ 7.14 (d, 2H), 7.09 (s, 2H), 7.04 (d, 2H), 6.96 (d, 2H), 6.91 (d, 2H), 6.36 (d, 2H), 6.32 (d, 2H), 4.17 (t, 4H), 2.53 (s, 6H), 1.61 (m, 4H), 1.20 (m, 36H), 0.87 (t, 6H); 13 CNMR (CDCl 3 ): 137.03, 136.62, 136.34, 135.83, 133.84, 131.10, 128.53, 6

128.20, 126.08, 125.90, 124.07, 123.75, 111.00, 45.40, 32.01, 31.21, 29.75, 29.63, 29.48, 29.45, 29.01, 26.46, 22.80, 22.21, 14.25; M(LDI-TOF) m/z 970.3 [M + ]. Anal. Calcd for C 54 H 70 N 2 7 : C, 66.75; H, 7.26; N, 2.88;, 23.10, found: C, 66.53; H, 7.37; N, 2.81. 1 H-NMR spectrum of Me-7TP-C 12 H 3 C N N CH 3 C 12 H 25 C 12 H 25 7

13 C-NMR spectrum of Me-7TP-C 12 H 3 C N N CH 3 C 12 H 25 C 12 H 25 imilar cross-coupling of the boronic acid pinacol ester prepared above with 5,5'-Dibromo-2,2'-bithiophene gave Me-8TP-C 12 (41%) as red solid: 1 HNMR (CDCl 3 ) δ 7.14(d, 2H), 7.10(s, 4H), 7.05(d, 2H), 6.97(d, 2H), 6.91(d, 2H), 6.36(d, 2H), 6.32(d, 2H), 4.17(t, 4H), 2.53 (s, 6H), 1.61(t, 4H), 1.20 (m, 36H), 0.87(t, 6H); 13 CNMR(CDCl 3, 100MHz) δ 136.99, 136.58, 136.25, 135.97, 135.66, 133.89, 131.10, 128.53, 128.17, 126.08, 125.89, 124.19, 124.09, 123.80, 110.99, 45.39, 32.00, 31.20, 29.75, 29.63, 29.48, 29.45, 29.00, 26.44, 22.80, 22.21, 14.25; M(LDI-TOF) m/z 1052 [M + ]. Anal. Calcd for C 58 H 72 N 2 8 :C, 66.11; H, 6.89; N, 2.66;, 24.34, found:c, 65.81; H, 7.05; N, 2.65. 8

1 H-NMR spectrum of Me-8TP-C 12 C 12 H 25 H 3 C N N CH 3 C 12 H 25 13 C-NMR spectrum of Me-8TP-C 12 C 12 H 25 H 3 C N N CH 3 C 12 H 25 9

Cross-coupling with 5,5 -Dibromo-2,2 :5,2 -terthiophene gave Me-9TP-C 12 (53%) as red-brown solid: 1 HNMR (CDCl 3 ) δ 7.15 (d, 2H), 7.10 (s, br, 6H), 7.04 (d, 2H), 6.97 (d, 2H), 6.91 (d, 2H), 6.36 (d, 2H), 6.32 (d, 2H), 4.17 (t, 4H), 2.53 (s, 6H), 1.61 (m, 4H), 1.10-1.36 (m, 36H), 0.87 (t, 6H); 13 CNMR(CDCl 3 ) δ 136.99, 136.59, 136.20, 136.05, 135.83, 135.58, 133.91, 131.09, 128.54, 128.17, 126.04, 125.87, 124.25, 124.21, 124.09, 123.83, 110.99, 45.38, 32.01, 31.20, 29.75, 29.63, 29.48, 29.45, 29.00, 26.44, 22.80, 22.20, 14.25; M(LDI-TOF) m/z 1135 [M + ]. Anal. Calcd for C62H74N29 :C, 65.56; H, 6.57; N, 2.47;, 25.41, found:c, 65.62; H, 6.58; N, 2.47. 1 H-NMR spectrum of Me-9TP-C 12 H 3 C N N CH 3 C 12 H 25 C 12 H 25 10

13 C-NMR spectrum of Me-9TP-C 12 H 3 C N N CH 3 C 12 H 25 C 12 H 25 ynthesis of 8TP-C 12. To a THF solution (8 ml) of 2 (m = 12) (582 mg, 1.33 mmol) and TMEDA (0.22 ml, 1.5 mmol) was added n-butyllithium (1.6 M, 1.5 mmol) in hexane at -78 C under N 2. After stirring for 40 min at 78 C, nme 3 Cl (1.0 M, 1.5 mmol) was added to the reaction mixture at 78 C and stirred additional 3h at rt. A standard workup using water and dichloromethane gave a crude trimethylstannane was obtained. To a mixture of the crude trimethylstannane, 5,5'-Dibromo-2,2'-bithiophene (160 mg, 0.49 mmol) and Pd (PPh 3 ) 4 (62 mg, 0.054 mmol) in a tube equipped with a stop cock were added THF (20 ml) under N 2. After heating at 70 C for 3d, a standard workup using NH 4 Cl aq and dichloromethane and separation with preparative gel permeation chromatography and column chromatography (Al 2 O 3 / CHCl 3 ) gave 8TP-C 12 (124 mg, 0.13 mmol, 26 %) as orange solid: 1 HNMR(500MHz, CDCl 3 ) δ 7.32 (dd, 2H), δ7.14 (d, 2H), δ7.11 7.08 (m, 8H), δ6.97(d, 2H), δ6.38 (d, 2H), δ6.34 (d, 2H), δ4.17 (t, 4H), δ1.57 1.62 (m, 4H), δ1.20 1.28 (m, 36H), δ0.87 (t, 6H); M (MALDI-TOF) m/z 961[M + ], matrix dithranol. 11

1 H-NMR spectrum of 8TP-C 12 C 12 H 25 N N C 12 H 25 ynthesis of Me-nTP-C m (bcl - 6 ) 2. To a C 2 solution (12 ml) of Me-6TP-C 12 (30 mg, 0.042 mmol) was slowly added bcl 5 (0.1 M, 0.12 mmol) in dichloromethane at rt under N 2. After stirring for 5 min at rt, the precipitate was collected on a filter and washed with C 2 and then with hexane gave Me-6TP-C 6 (bcl - 6 ) 2. (52 mg, 0.038 mmol, 94%) as deep purple solid: Anal. Calcd for C38H44Cl12N26b2: C, 32.83; H, 3.19; N, 2.02; Cl; 30.60; ; 13.84; b; 17.52. Found: C, 32.95; H, 3.28; N, 2.01. Me-7TP-C 12 (bcl - 6 ) 2. (85%) as deep purple solid: Anal. Calcd for C54H70Cl12N27b2: C, 39.53; H, 4.30; N, 1.71; Cl; 25.93; ; 13.68; b; 14.84. Found: C, 39.24; H, 4.30; N, 1.73. Me-8TP-C 12 (bcl - 6 ) 2. (81%) as deep purple solid: Anal. Calcd for C58H72Cl12N28b2: C, 40.44; H, 4.21; N, 1.63; Cl; 24.70; ; 14.89; b; 14.14. Found: C, 40.26; H, 4.15; N, 1.60. Me-9TP-C 12 (bcl - 6 ) 2. (94%) as deep purple solid: Anal. Calcd for C62H74Cl12N29b2: C, 41.26; H, 4.13; N, 1.55; Cl; 23.57; ; 15.99; b; 13.49. Found: C, 41.02; H, 4.04; N, 1.59. 12

Ref. 1. J. Nakazaki, I. Chung, M. M. Matsushita, T. ugawara, R. Watanabe, A. Izuoka and Y. Kawada, J. Mater. Chem., 2003, 13, 1011. 2. R. E. Niziurski-Mann and M. P. Cava, Adv. Mater., 1993, 5, 547. 3. P. A. Chaloner,. R. Gunatunga, and P. B. Hitchgcock, J. Chem. oc., Perkin Trans. 2, 1997, 1597. 4. K. Yui, Y. Aso, T. Otsubo, and F. Ogura, Bull. Chem. oc. Jpn., 1989, 62, 1539. 5. Gaussian 03, Revision E.01, M. J. Frisch, G. W. Trucks, H. B. chlegel, G. E. cuseria, M. A. Robb, J. R. Cheeseman, J. A. Montgomery, Jr., T. Vreven, K. N. Kudin, J. C. Burant, J. M. Millam,.. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. calmani, N. Rega, G. A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J. E. Knox, H. P. Hratchian, J. B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R. E. tratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, P. Y. Ayala, K. Morokuma, G. A. Voth, P. alvador, J. J. Dannenberg, V. G. Zakrzewski,. Dapprich, A. D. Daniels, M. C. train, O. Farkas, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. V. Ortiz, Q. Cui, A. G. Baboul,. Clifford, J. Cioslowski, B. B. tefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, M. Challacombe, P. M. W. Gill, B. Johnson, W. Chen, M. W. Wong, C. Gonzalez and J. A. Pople, Gaussian, Inc., Wallingford CT, 2004. 13

(a) (b) (c) Figure 1. pin distributions of the singlet biradicals of (a) 8T 2+, (b) 8TP-C 1 2+ and (c) Me-nTP-C 1 2+. 14

Me 12 11 8 9 10 7 N R 6 5 4 3 10 1 Me 11 2 14 12 13 9 N R 8 7 6 5 3 2 1 4 Me-6TP TP-C1 2+ Me-7TP TP-C1 2+ Me 16 15 12 13 14 11 10 9 N 8 R 7 5 4 3 6 13 14 12 2 1 Me 15 11 N 18 16 10 17 R 9 7 6 5 8 4 3 2 1 Me-8TP TP-C1 2+ Me-9TP TP-C1 2+ (a) (b) 1.46 1.46 1.44 1.44 1.42 1.4 1.38 1.36 1.42 1.4 1.38 1.34 1.36 1.32 1 2 3 4 5 6 7 8 9 10 11 12 1.34 1 2 3 4 5 6 7 8 9 10 11 12 13 14 (c) (d) 1.45 1.44 1.43 1.42 1.41 1.4 1.39 1.38 1.37 1.36 1.35 1.34 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 1.45 1.44 1.43 1.42 1.41 1.4 1.39 1.38 1.37 1.36 1.35 1.34 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 1234567891 singlet(r) triplet singlet(u) Figure 2. Pattern of C-C bond length alternation of (a) Me-6TP-C 2+ 1, (b) Me-7TP-C 2+ 1, (c) Me-8TP-C 2+ 1 and (d) Me-9TP-C 2+ 1. For the numbering of bond position, see the above structures. 15

(a) (b) (c) (d) (e) 2e - 1e - 1e - Figure 3. Cyclic voltammogram of (a) Me-6TP-C 6, (b) Me-7TP-C 12, (c) Me-8TP-C 12 and (d) Me-9TP-C 12. (e) Linear sweep voltammetry of Me-9TP-C 12. Conditions: n-bu 4 N + PF 6 (0.1M) in dry CH 2 Cl 2 under N 2 at r.t; reference electrode: Ag/Ag + (0.01M AgNO 3 in MeCN); working electrode: glassy carbon. Potentials are referred to Fc/Fc +. 16

(a) (b) Figure 4. Cyclic voltamograms of (a) 6TP and (b) 8TP. Conditions: n-bu 4 N + PF 6 - (0.1M) in dry CH 2 Cl 2 under N 2 at r.t; reference electrode: Ag/Ag + (0.01M AgNO 3 in MeCN); working electrode: glassy carbon. Potentials are referred to Fc/Fc +. (a) (b) 500 250 (c) (d) 50 100 Figure 5. ER spectra of (a) Me-6TPC 6 2+ (bcl 6 ) 2, (b) Me-7TPC 12 2+ (bcl 6 ) 2, (c) Me-8TPC 12 2+ (bcl 6 ) 2 and (d) Me-9TPC 12 2+ (bcl 6 ) 2 in the solid state at rt. 17

0.5 5.0 χ p T / emu K mol -1 0.4 0.3 0.2 0.1 χ p T / 10-2 emu K mol -1 4.8 4.6 4.4 4.2 4.0 100 150 200 T / K 250 300 0.0 50 100 150 200 250 300 T / K Figure 6. Thermal dependence of χ M T for Me-9TPC 9TPC12 2+ (bcl6 - )2; ( ) experimental χ M T data; and the fitting curve (red solid lines) are drawn using the Bleaney Bowers equation with Curie impurity term; spin contamination = 11.1 % for g = 2.00 and = 1/2, diamagnetic susceptibility = 1.26 10 3 emu mol 1, and T gap = 2000 K. 18

Table 1. The 2 2+ (before annihilation) values for pin-unrestricted inglet tates of Me-nTP-C 1 and nt 2+. compd 2 compd 2 6T 2+ 0.32 a 2+ Me-6TP-C 1 0.76 7T 2+ 0.60 a 2+ Me-7TP-C 1 0.88 8T 2+ 0.77 a 2+ Me-8TP-C 1 0.93 9T 2+ 0.86 a 2+ Me-9TP-C 1 0.97 a Data from Zade,..; Bendikov, M. J. Phys. Chem. B 2006, 110, 15839. Table 2. Observed and calculated (TD-B3LYP/6-31G(d)) absorption maxima with the values of absorption coefficients (ε) and oscillator strengths(f) 2+ Me-6TP-C 1 2+ Me-7TP-C 1 2+ Me-8TP-C 1 2+ Me-9TP-C 1 Observed λ max [nm](ε) 560 (19000) 965 (141000) 585 (25400) 1093 (138000) 648 (31500) 1212 (63900) 692(48900) 1275 (48900) R(2, 1) 428 (0.12) 468 (0.30) 515 (0.51) 558 (0.80) λ max [nm](f) 912 (2.91) 1041 (3.26) 1181 (3.53) 1337 (3.68) T(2, 3) 588 (0.32) 510 (0.42) 558 (0.97) 600 (1.28) λ max [nm](f) 630 (1.41) 699 (1.52) 756 (1.54) 812 (1.27) 1053 (0.76) 1201 (0.91) 1349 (1.10) 1504 (1.30) U(B) 622 (1.05) 612 (1.32) 648 (1.75) 683 (1.94) λ max [nm](f) 996 (1.62) 1137 (1.85) 1283 (1.94) 1438 (2.04) 19

Table 3. Cartesian Coordinate of the optimized structure for pin-restricted inglet (R) 6TP-C1 at the B3LYP/6-31G(d) level. Center Atomic Atomic Coordinates (Angstroms) Number Number Type X Y Z 1 6 0-0.129003 0.684741-0.028447 2 6 0-1.395292 1.332565-0.068343 3 6 0-1.329112 2.703494-0.056840 4 6 0 0.000874 3.220562-0.017900 5 16 0 1.158565 1.888443 0.036391 6 6 0 0.467430 4.537810-0.062504 7 6 0 1.802071 4.959108-0.362602 8 6 0 1.824200 6.325387-0.390214 9 6 0 0.502742 6.795011-0.097888 10 7 0-0.299196 5.699977 0.113174 11 6 0 0.085489 8.156294-0.051871 12 6 0-1.178780 8.733587-0.213283 13 6 0-1.158565 10.138753-0.164826 14 6 0 0.111370 10.644154 0.036791 15 16 0 1.301992 9.416492 0.157228 16 6 0 0.129003-0.684741-0.028447 17 6 0 1.395292-1.332565-0.068343 18 6 0 1.329112-2.703494-0.056840 19 6 0-0.000874-3.220562-0.017900 20 16 0-1.158565-1.888443 0.036391 21 6 0-0.467430-4.537810-0.062504 22 6 0-1.802071-4.959108-0.362602 23 6 0-1.824200-6.325387-0.390214 24 6 0-0.502742-6.795011-0.097888 25 7 0 0.299196-5.699977 0.113174 26 6 0-0.085489-8.156294-0.051871 27 6 0 1.178780-8.733587-0.213283 28 6 0 1.158565-10.138753-0.164826 29 6 0-0.111370-10.644154 0.036791 30 16 0-1.301992-9.416492 0.157228 20

31 6 0-1.628833 5.746647 0.727872 32 1 0-2.327850 0.782174-0.133480 33 1 0-2.205569 3.331810-0.135491 34 1 0 2.622794 4.294829-0.597848 35 1 0 2.661210 6.960193-0.645621 36 1 0-2.078189 8.165630-0.414993 37 1 0-2.035754 10.763888-0.282326 38 1 0 0.401311 11.683588 0.128247 39 1 0-2.421664 5.705322-0.025502 40 1 0-1.733083 4.911241 1.420914 41 1 0-1.721838 6.672140 1.296315 42 6 0 1.628833-5.746647 0.727872 43 1 0 2.327850-0.782174-0.133480 44 1 0 2.205569-3.331810-0.135491 45 1 0-2.622794-4.294829-0.597848 46 1 0-2.661210-6.960193-0.645621 47 1 0 2.078189-8.165630-0.414993 48 1 0 2.035754-10.763888-0.282326 49 1 0-0.401311-11.683588 0.128247 50 1 0 2.421664-5.705322-0.025502 51 1 0 1.733083-4.911241 1.420914 52 1 0 1.721838-6.672140 1.296315 E(RB+HF-LYP) = -2704.51980947 hartree Table 4. Cartesian Coordinate of the optimized structure for pin-unrestricted inglet (U) 6TP-C1 at the B3LYP/6-31G(d) level. Center Atomic Atomic Coordinates (Angstroms) Number Number Type X Y Z 1 6 0-0.143454 0.689598-0.084470 2 6 0-1.410539 1.312706-0.127632 3 6 0-1.361252 2.693563-0.110874 4 6 0-0.045946 3.220327-0.063395 5 16 0 1.126225 1.904067-0.011895 21

6 6 0 0.412288 4.550621-0.104425 7 6 0 1.732017 4.986973-0.436359 8 6 0 1.742270 6.355321-0.433799 9 6 0 0.427432 6.806972-0.092426 10 7 0-0.358771 5.695099 0.118369 11 6 0-0.001887 8.160676-0.006773 12 6 0-1.279786 8.727411-0.098747 13 6 0-1.271748 10.130543-0.029112 14 6 0 0.001887 10.647674 0.120186 15 16 0 1.210169 9.431888 0.165953 16 6 0 0.143454-0.689598-0.084470 17 6 0 1.410539-1.312706-0.127632 18 6 0 1.361252-2.693563-0.110874 19 6 0 0.045946-3.220327-0.063395 20 16 0-1.126225-1.904067-0.011895 21 6 0-0.412288-4.550621-0.104425 22 6 0-1.732017-4.986973-0.436359 23 6 0-1.742270-6.355321-0.433799 24 6 0-0.427432-6.806972-0.092426 25 7 0 0.358771-5.695099 0.118369 26 6 0 0.001887-8.160676-0.006773 27 6 0 1.279786-8.727411-0.098747 28 6 0 1.271748-10.130543-0.029112 29 6 0-0.001887-10.647674 0.120186 30 16 0-1.210169-9.431888 0.165953 31 6 0-1.671611 5.711713 0.769659 32 1 0-2.336480 0.752013-0.197368 33 1 0-2.245737 3.310691-0.192507 34 1 0 2.549569 4.334198-0.710874 35 1 0 2.566590 7.002058-0.700567 36 1 0-2.182078 8.153018-0.265330 37 1 0-2.159811 10.747847-0.095298 38 1 0 0.284414 11.689037 0.213319 39 1 0-2.483806 5.699920 0.036172 40 1 0-1.755945 4.845651 1.426634 41 1 0-1.751122 6.610551 1.381319 22

42 6 0 1.671611-5.711713 0.769659 43 1 0 2.336480-0.752013-0.197368 44 1 0 2.245737-3.310691-0.192507 45 1 0-2.549569-4.334198-0.710874 46 1 0-2.566590-7.002058-0.700567 47 1 0 2.182078-8.153018-0.265330 48 1 0 2.159811-10.747847-0.095298 49 1 0-0.284414-11.689037 0.213319 50 1 0 2.483806-5.699920 0.036172 51 1 0 1.755945-4.845651 1.426634 52 1 0 1.751122-6.610551 1.381319 E(UB+HF-LYP) = -2704.52053363 hartree Table 5. Cartesian Coordinate of the optimized structure for Triplet (T) 6TP-C1 at the B3LYP/6-31G(d) level. Center Atomic Atomic Coordinates (Angstroms) Number Number Type X Y Z 1 6 0-0.169316 0.700911-0.192457 2 6 0-1.432009 1.283337-0.252124 3 6 0-1.406618 2.685452-0.232904 4 6 0-0.117975 3.219483-0.162259 5 16 0 1.073022 1.926334-0.105374 6 6 0 0.336036 4.573959-0.198582 7 6 0 1.621564 5.029113-0.611838 8 6 0 1.628777 6.398898-0.538089 9 6 0 0.343728 6.824624-0.079873 10 7 0-0.420602 5.684761 0.135305 11 6 0-0.090292 8.163688 0.091430 12 6 0-1.380532 8.716449 0.162304 13 6 0-1.380532 10.113631 0.274178 14 6 0-0.101846 10.647165 0.295783 15 16 0 1.119774 9.449992 0.169357 16 6 0 0.169316-0.700911-0.192457 23

17 6 0 1.432009-1.283337-0.252124 18 6 0 1.406618-2.685452-0.232904 19 6 0 0.117975-3.219483-0.162259 20 16 0-1.073022-1.926334-0.105374 21 6 0-0.336036-4.573959-0.198582 22 6 0-1.621564-5.029113-0.611838 23 6 0-1.628777-6.398898-0.538089 24 6 0-0.343728-6.824624-0.079873 25 7 0 0.420602-5.684761 0.135305 26 6 0 0.090292-8.163688 0.091430 27 6 0 1.380532-8.716449 0.162304 28 6 0 1.380532-10.113631 0.274178 29 6 0 0.101846-10.647165 0.295783 30 16 0-1.119774-9.449992 0.169357 31 6 0-1.691934 5.650963 0.863940 32 1 0-2.348544 0.708928-0.330264 33 1 0-2.301299 3.287396-0.326455 34 1 0 2.415865 4.393437-0.977972 35 1 0 2.430938 7.061775-0.832104 36 1 0-2.288726 8.133717 0.082945 37 1 0-2.277067 10.719941 0.327292 38 1 0 0.175235 11.690196 0.387844 39 1 0-2.545559 5.719127 0.182522 40 1 0-1.751792 4.721809 1.430723 41 1 0-1.720236 6.483271 1.567554 42 6 0 1.691934-5.650963 0.863940 43 1 0 2.348544-0.708928-0.330264 44 1 0 2.301299-3.287396-0.326455 45 1 0-2.415865-4.393437-0.977972 46 1 0-2.430938-7.061775-0.832104 47 1 0 2.288726-8.133717 0.082945 48 1 0 2.277067-10.719941 0.327292 49 1 0-0.175235-11.690196 0.387844 50 1 0 2.545559-5.719127 0.182522 51 1 0 1.751792-4.721809 1.430723 52 1 0 1.720236-6.483271 1.567554 24

E(UB+HF-LYP) = -2704.51295320 hartree Table 6. Cartesian Coordinate of the optimized structure for pin-restricted inglet (R) 7TP-C1 at the B3LYP/6-31G(d) level. Center Atomic Atomic Coordinates (Angstroms) Number Number Type X Y Z 1 6 0 0.004017 0.687036-1.544549 2 6 0 0.007670 1.266244-0.246964 3 6 0 0.012481 2.624974 0.080501 4 6 0 0.047662 3.214565 1.369050 5 6 0 0.041325 4.591470 1.362572 6 6 0 0.012968 5.163081 0.060140 7 6 0 0.064752 6.503456-0.352805 8 6 0 0.395632 6.982175-1.654778 9 6 0 0.410185 8.352761-1.617265 10 6 0 0.078807 8.760010-0.290546 11 6 0 0.000000 10.103099 0.190510 12 6 0 0.150140 10.621606 1.477803 13 6 0 0.068955 12.027584 1.525460 14 6 0-0.145638 12.588578 0.284135 15 16 0 0.000000 0.000000 0.981329 16 16 0-0.038703 3.885153-1.152878 17 16 0-0.242924 11.412124-0.963438 18 7 0-0.139553 7.628249 0.458763 19 1 0 0.007946 1.286131-2.448626 20 1 0 0.101086 2.624850 2.278077 21 1 0 0.114640 5.181605 2.265703 22 1 0 0.660754 6.356037-2.496082 23 1 0 0.682324 9.025295-2.418667 24 1 0 0.366351 10.015012 2.348394 25 1 0 0.173549 12.611091 2.432511 26 1 0-0.260007 13.637767 0.042566 27 6 0-0.785919 7.611208 1.772740 25

28 1 0-0.051813 7.540854 2.581644 29 1 0-1.472573 6.765497 1.824106 30 1 0-1.363509 8.527872 1.893455 31 6 0-0.004017-0.687036-1.544549 32 6 0-0.007670-1.266244-0.246964 33 6 0-0.012481-2.624974 0.080501 34 6 0-0.047662-3.214565 1.369050 35 6 0-0.041325-4.591470 1.362572 36 6 0-0.012968-5.163081 0.060140 37 6 0-0.064752-6.503456-0.352805 38 6 0-0.395632-6.982175-1.654778 39 6 0-0.410185-8.352761-1.617265 40 6 0-0.078807-8.760010-0.290546 41 6 0 0.000000-10.103099 0.190510 42 6 0-0.150140-10.621606 1.477803 43 6 0-0.068955-12.027584 1.525460 44 6 0 0.145638-12.588578 0.284135 45 16 0 0.038703-3.885153-1.152878 46 16 0 0.242924-11.412124-0.963438 47 7 0 0.139553-7.628249 0.458763 48 1 0-0.007946-1.286131-2.448626 49 1 0-0.101086-2.624850 2.278077 50 1 0-0.114640-5.181605 2.265703 51 1 0-0.660754-6.356037-2.496082 52 1 0-0.682324-9.025295-2.418667 53 1 0-0.366351-10.015012 2.348394 54 1 0-0.173549-12.611091 2.432511 55 1 0 0.260007-13.637767 0.042566 56 6 0 0.785919-7.611208 1.772740 57 1 0 0.051813-7.540854 2.581644 58 1 0 1.472573-6.765497 1.824106 59 1 0 1.363509-8.527872 1.893455 E(RB+HF-LYP) = -3256.35078511 hartree Table 7. Cartesian Coordinate of the optimized structure for pin-unrestricted inglet (U) 26

7TP-C1 at the B3LYP/6-31G(d) level. Center Atomic Atomic Coordinates (Angstroms) Number Number Type X Y Z 1 6 0 0.012452 0.694327-1.541673 2 6 0 0.022119 1.261991-0.256285 3 6 0 0.043004 2.636221 0.089484 4 6 0 0.087958 3.211331 1.371820 5 6 0 0.092943 4.598918 1.369411 6 6 0 0.061132 5.167407 0.077669 7 6 0 0.123898 6.515118-0.341533 8 6 0 0.487635 6.988912-1.635812 9 6 0 0.485701 8.360291-1.604624 10 6 0 0.114713 8.770853-0.289240 11 6 0 0.015662 10.111741 0.184982 12 6 0 0.098275 10.634329 1.479487 13 6 0 0.018273 12.038780 1.519526 14 6 0-0.128922 12.598379 0.266199 15 16 0 0.000000 0.000000 0.968170 16 16 0 0.000000 3.892560-1.137091 17 16 0-0.163370 11.420346-0.983139 18 7 0-0.114007 7.633675 0.458472 19 1 0 0.024081 1.290511-2.447601 20 1 0 0.137594 2.619208 2.279222 21 1 0 0.175881 5.184667 2.275050 22 1 0 0.781288 6.360299-2.465443 23 1 0 0.772571 9.031313-2.402278 24 1 0 0.265297 10.029876 2.361974 25 1 0 0.076257 12.624427 2.429373 26 1 0-0.227137 13.647632 0.017640 27 6 0-0.789980 7.610016 1.757442 28 1 0-0.072532 7.572498 2.583270 29 1 0-1.446848 6.740838 1.802854 30 1 0-1.402337 8.506775 1.853822 31 6 0-0.012452-0.694327-1.541673 27

32 6 0-0.022119-1.261991-0.256285 33 6 0-0.043004-2.636221 0.089484 34 6 0-0.087958-3.211331 1.371820 35 6 0-0.092943-4.598918 1.369411 36 6 0-0.061132-5.167407 0.077669 37 6 0-0.123898-6.515118-0.341533 38 6 0-0.487635-6.988912-1.635812 39 6 0-0.485701-8.360291-1.604624 40 6 0-0.114713-8.770853-0.289240 41 6 0-0.015662-10.111741 0.184982 42 6 0-0.098275-10.634329 1.479487 43 6 0-0.018273-12.038780 1.519526 44 6 0 0.128922-12.598379 0.266199 45 16 0 0.000000-3.892560-1.137091 46 16 0 0.163370-11.420346-0.983139 47 7 0 0.114007-7.633675 0.458472 48 1 0-0.024081-1.290511-2.447601 49 1 0-0.137594-2.619208 2.279222 50 1 0-0.175881-5.184667 2.275050 51 1 0-0.781288-6.360299-2.465443 52 1 0-0.772571-9.031313-2.402278 53 1 0-0.265297-10.029876 2.361974 54 1 0-0.076257-12.624427 2.429373 55 1 0 0.227137-13.647632 0.017640 56 6 0 0.789980-7.610016 1.757442 57 1 0 0.072532-7.572498 2.583270 58 1 0 1.446848-6.740838 1.802854 59 1 0 1.402337-8.506775 1.853822 E(UB+HF-LYP) = -3256.35308010 hartree Table 8. Cartesian Coordinate of the optimized structure for Triplet (T) 7TP-C1 2+ at the B3LYP/6-31G(d) level. Center Atomic Atomic Coordinates (Angstroms) Number Number Type X Y Z 28

1 6 0 0.017982 0.701415-1.540170 2 6 0 0.031286 1.258110-0.265736 3 6 0 0.065392 2.646789 0.099115 4 6 0 0.119099 3.207452 1.376428 5 6 0 0.132862 4.605363 1.378995 6 6 0 0.095804 5.171556 0.097803 7 6 0 0.165301 6.526599-0.327610 8 6 0 0.563399 6.996456-1.612899 9 6 0 0.538560 8.368322-1.590231 10 6 0 0.123772 8.781366-0.288718 11 6 0 0.000000 10.119312 0.177326 12 6 0 0.007925 10.646292 1.475788 13 6 0-0.074789 12.048688 1.507972 14 6 0-0.150790 12.606742 0.245671 15 16 0 0.000000 0.000000 0.955290 16 16 0 0.028919 3.899797-1.119915 17 16 0-0.114027 11.427554-1.002171 18 7 0-0.112466 7.637797 0.457909 19 1 0 0.034992 1.294910-2.447780 20 1 0 0.164966 2.612413 2.281836 21 1 0 0.223511 5.186585 2.287321 22 1 0 0.889365 6.366138-2.428772 23 1 0 0.838303 9.038332-2.384141 24 1 0 0.123360 10.044078 2.367629 25 1 0-0.068899 12.636698 2.418141 26 1 0-0.234749 13.655864-0.008931 27 6 0-0.818832 7.605600 1.740540 28 1 0-0.120302 7.604876 2.583229 29 1 0-1.441015 6.711240 1.781789 30 1 0-1.468263 8.478472 1.809712 31 6 0-0.017982-0.701415-1.540170 32 6 0-0.031286-1.258110-0.265736 33 6 0-0.065392-2.646789 0.099115 34 6 0-0.119099-3.207452 1.376428 35 6 0-0.132862-4.605363 1.378995 29

36 6 0-0.095804-5.171556 0.097803 37 6 0-0.165301-6.526599-0.327610 38 6 0-0.563399-6.996456-1.612899 39 6 0-0.538560-8.368322-1.590231 40 6 0-0.123772-8.781366-0.288718 41 6 0 0.000000-10.119312 0.177326 42 6 0-0.007925-10.646292 1.475788 43 6 0 0.074789-12.048688 1.507972 44 6 0 0.150790-12.606742 0.245671 45 16 0-0.028919-3.899797-1.119915 46 16 0 0.114027-11.427554-1.002171 47 7 0 0.112466-7.637797 0.457909 48 1 0-0.034992-1.294910-2.447780 49 1 0-0.164966-2.612413 2.281836 50 1 0-0.223511-5.186585 2.287321 51 1 0-0.889365-6.366138-2.428772 52 1 0-0.838303-9.038332-2.384141 53 1 0-0.123360-10.044078 2.367629 54 1 0 0.068899-12.636698 2.418141 55 1 0 0.234749-13.655864-0.008931 56 6 0 0.818832-7.605600 1.740540 57 1 0 0.120302-7.604876 2.583229 58 1 0 1.441015-6.711240 1.781789 59 1 0 1.468263-8.478472 1.809712 E(UB+HF-LYP) = -3256.34816393 hartree Table 9. Cartesian Coordinate of the optimized structure for pin-restricted inglet (R) 8TP-C1 at the B3LYP/6-31G(d) level. Center Atomic Atomic Coordinates (Angstroms) Number Number Type X Y Z 1 6 0-0.045228 0.698987-0.059880 2 6 0-1.215830 1.496376-0.070009 3 6 0-0.972027 2.852369-0.071760 30

4 6 0 0.404143 3.190719-0.063742 5 6 0 0.973165 4.472395-0.064897 6 6 0 2.341402 4.821132-0.107431 7 6 0 2.581347 6.181052-0.099240 8 6 0 1.405330 6.972487-0.060066 9 6 0 1.234974 8.369510-0.106252 10 6 0 0.045228 9.073352-0.439968 11 6 0 0.327360 10.418956-0.438756 12 6 0 1.698324 10.578718-0.095453 13 6 0 2.416774 11.813497 0.004845 14 6 0 3.772153 12.092987-0.158128 15 6 0 4.076661 13.466654-0.047118 16 6 0 2.963350 14.237964 0.202138 17 16 0 1.387139 1.728889-0.047309 18 16 0-0.014330 5.931800 0.000696 19 16 0 1.523831 13.301774 0.299332 20 7 0 2.232317 9.327923 0.113907 21 1 0-2.212099 1.067717-0.081282 22 1 0-1.755415 3.602185-0.084971 23 1 0 3.130649 4.079349-0.169613 24 1 0 3.574657 6.600872-0.179509 25 1 0-0.891680 8.609645-0.717808 26 1 0-0.338705 11.226408-0.708666 27 1 0 4.513900 11.343019-0.403769 28 1 0 5.073663 13.877034-0.155984 29 1 0 2.917040 15.310328 0.342392 30 6 0 3.519758 9.069599 0.760463 31 1 0 4.303640 8.856490 0.026534 32 1 0 3.416857 8.224606 1.442447 33 1 0 3.805202 9.947107 1.340894 34 6 0 0.045228-0.698987-0.059880 35 6 0 1.215830-1.496376-0.070009 36 6 0 0.972027-2.852369-0.071760 37 6 0-0.404143-3.190719-0.063742 38 6 0-0.973165-4.472395-0.064897 39 6 0-2.341402-4.821132-0.107431 31

40 6 0-2.581347-6.181052-0.099240 41 6 0-1.405330-6.972487-0.060066 42 6 0-1.234974-8.369510-0.106252 43 6 0-0.045228-9.073352-0.439968 44 6 0-0.327360-10.418956-0.438756 45 6 0-1.698324-10.578718-0.095453 46 6 0-2.416774-11.813497 0.004845 47 6 0-3.772153-12.092987-0.158128 48 6 0-4.076661-13.466654-0.047118 49 6 0-2.963350-14.237964 0.202138 50 16 0-1.387139-1.728889-0.047309 51 16 0 0.014330-5.931800 0.000696 52 16 0-1.523831-13.301774 0.299332 53 7 0-2.232317-9.327923 0.113907 54 1 0 2.212099-1.067717-0.081282 55 1 0 1.755415-3.602185-0.084971 56 1 0-3.130649-4.079349-0.169613 57 1 0-3.574657-6.600872-0.179509 58 1 0 0.891680-8.609645-0.717808 59 1 0 0.338705-11.226408-0.708666 60 1 0-4.513900-11.343019-0.403769 61 1 0-5.073663-13.877034-0.155984 62 1 0-2.917040-15.310328 0.342392 63 6 0-3.519758-9.069599 0.760463 64 1 0-4.303640-8.856490 0.026534 65 1 0-3.416857-8.224606 1.442447 66 1 0-3.805202-9.947107 1.340894 E(RB+HF-LYP) = -3808.17846970 hartree Table 10. Cartesian Coordinate of the optimized structure for pin-unrestricted inglet (U) 8TP-C1 2+ at the B3LYP/6-31G(d) level. Center Atomic Atomic Coordinates (Angstroms) Number Number Type X Y Z 32

1 6 0-0.176964 0.677734-0.077724 2 6 0-1.477460 1.238702-0.089976 3 6 0-1.495182 2.616323-0.091276 4 6 0-0.208201 3.209532-0.079663 5 6 0 0.107319 4.575915-0.076771 6 6 0 1.384690 5.178269-0.108341 7 6 0 1.361939 6.559018-0.096012 8 6 0 0.056784 7.112531-0.065278 9 6 0-0.375398 8.451954-0.111307 10 6 0-1.673222 8.918291-0.457960 11 6 0-1.651715 10.293023-0.451317 12 6 0-0.340161 10.708850-0.091008 13 6 0 0.129201 12.057130 0.021599 14 6 0 1.408745 12.589993-0.121905 15 6 0 1.445041 13.995922-0.003339 16 6 0 0.202239 14.540289 0.232433 17 16 0 1.034193 1.960592-0.062166 18 16 0-1.139890 5.821095-0.017645 19 16 0-1.034193 13.347065 0.307389 20 7 0 0.419360 9.581354 0.122239 21 1 0-2.374386 0.628970-0.103263 22 1 0-2.406541 3.203948-0.105586 23 1 0 2.300933 4.600070-0.164879 24 1 0 2.258028 7.160136-0.167490 25 1 0-2.501639 8.286156-0.748004 26 1 0-2.455860 10.960288-0.728034 27 1 0 2.282860 11.995983-0.358629 28 1 0 2.347161 14.588878-0.097447 29 1 0-0.049023 15.583566 0.374572 30 6 0 1.724058 9.569343 0.785311 31 1 0 2.543545 9.516594 0.061303 32 1 0 1.776303 8.714548 1.460751 33 1 0 1.828516 10.480297 1.375019 34 6 0 0.176964-0.677734-0.077724 35 6 0 1.477460-1.238702-0.089976 36 6 0 1.495182-2.616323-0.091276 33

37 6 0 0.208201-3.209532-0.079663 38 6 0-0.107319-4.575915-0.076771 39 6 0-1.384690-5.178269-0.108341 40 6 0-1.361939-6.559018-0.096012 41 6 0-0.056784-7.112531-0.065278 42 6 0 0.375398-8.451954-0.111307 43 6 0 1.673222-8.918291-0.457960 44 6 0 1.651715-10.293023-0.451317 45 6 0 0.340161-10.708850-0.091008 46 6 0-0.129201-12.057130 0.021599 47 6 0-1.408745-12.589993-0.121905 48 6 0-1.445041-13.995922-0.003339 49 6 0-0.202239-14.540289 0.232433 50 16 0-1.034193-1.960592-0.062166 51 16 0 1.139890-5.821095-0.017645 52 16 0 1.034193-13.347065 0.307389 53 7 0-0.419360-9.581354 0.122239 54 1 0 2.374386-0.628970-0.103263 55 1 0 2.406541-3.203948-0.105586 56 1 0-2.300933-4.600070-0.164879 57 1 0-2.258028-7.160136-0.167490 58 1 0 2.501639-8.286156-0.748004 59 1 0 2.455860-10.960288-0.728034 60 1 0-2.282860-11.995983-0.358629 61 1 0-2.347161-14.588878-0.097447 62 1 0 0.049023-15.583566 0.374572 63 6 0-1.724058-9.569343 0.785311 64 1 0-2.543545-9.516594 0.061303 65 1 0-1.776303-8.714548 1.460751 66 1 0-1.828516-10.480297 1.375019 E(UB+HF-LYP) = -3808.17852677 hartree Table 11. Cartesian Coordinate of the optimized structure for Triplet (T) 8TP-C1 2+ at the B3LYP/6-31G(d) level. 34

Center Atomic Atomic Coordinates (Angstroms) Number Number Type X Y Z 1 6 0-0.194071 0.692195-0.131975 2 6 0-1.476519 1.231791-0.164118 3 6 0-1.496856 2.633888-0.162531 4 6 0-0.230324 3.211613-0.127925 5 6 0 0.114359 4.599730-0.120597 6 6 0 1.388097 5.178437-0.141224 7 6 0 1.375908 6.573000-0.121618 8 6 0 0.086335 7.128080-0.092014 9 6 0-0.349121 8.477324-0.135081 10 6 0-1.637981 8.946114-0.518247 11 6 0-1.623860 10.318999-0.471172 12 6 0-0.325545 10.732062-0.055198 13 6 0 0.135593 12.073119 0.094451 14 6 0 1.426374 12.608127 0.051935 15 6 0 1.453426 14.010526 0.175299 16 6 0 0.194071 14.556247 0.315909 17 16 0 1.007991 1.966200-0.091197 18 16 0-1.119006 5.841553-0.069489 19 16 0-1.046466 13.366325 0.292337 20 7 0 0.430199 9.592493 0.157401 21 1 0-2.373863 0.623749-0.196550 22 1 0-2.411814 3.215592-0.192974 23 1 0 2.299425 4.592813-0.190381 24 1 0 2.279193 7.165381-0.183786 25 1 0-2.451393 8.316337-0.851494 26 1 0-2.422132 10.989575-0.757470 27 1 0 2.316278 12.015066-0.116797 28 1 0 2.359864 14.603889 0.152027 29 1 0-0.065052 15.599966 0.440608 30 6 0 1.713816 9.559153 0.860346 31 1 0 2.555040 9.541917 0.160098 32 1 0 1.749978 8.673601 1.495847 33 1 0 1.792717 10.441726 1.495204 35

34 6 0 0.194071-0.692195-0.131975 35 6 0 1.476519-1.231791-0.164118 36 6 0 1.496856-2.633888-0.162531 37 6 0 0.230324-3.211613-0.127925 38 6 0-0.114359-4.599730-0.120597 39 6 0-1.388097-5.178437-0.141224 40 6 0-1.375908-6.573000-0.121618 41 6 0-0.086335-7.128080-0.092014 42 6 0 0.349121-8.477324-0.135081 43 6 0 1.637981-8.946114-0.518247 44 6 0 1.623860-10.318999-0.471172 45 6 0 0.325545-10.732062-0.055198 46 6 0-0.135593-12.073119 0.094451 47 6 0-1.426374-12.608127 0.051935 48 6 0-1.453426-14.010526 0.175299 49 6 0-0.194071-14.556247 0.315909 50 16 0-1.007991-1.966200-0.091197 51 16 0 1.119006-5.841553-0.069489 52 16 0 1.046466-13.366325 0.292337 53 7 0-0.430199-9.592493 0.157401 54 1 0 2.373863-0.623749-0.196550 55 1 0 2.411814-3.215592-0.192974 56 1 0-2.299425-4.592813-0.190381 57 1 0-2.279193-7.165381-0.183786 58 1 0 2.451393-8.316337-0.851494 59 1 0 2.422132-10.989575-0.757470 60 1 0-2.316278-12.015066-0.116797 61 1 0-2.359864-14.603889 0.152027 62 1 0 0.065052-15.599966 0.440608 63 6 0-1.713816-9.559153 0.860346 64 1 0-2.555040-9.541917 0.160098 65 1 0-1.749978-8.673601 1.495847 66 1 0-1.792717-10.441726 1.495204 E(UB+HF-LYP) = -3808.17902769 hartree 36

Table 12. Cartesian Coordinate of the optimized structure for pin-restricted inglet (R) 9TP-C1 at the B3LYP/6-31G(d) level. Center Atomic Atomic Coordinates (Angstroms) Number Number Type X Y Z 1 16 0 0.000000 0.000000 1.106416 2 6 0-0.011786 1.265689-0.119388 3 6 0-0.005996 0.690539-1.410063 4 6 0-0.026038 2.628710 0.222643 5 6 0-0.048672 3.201866 1.512769 6 6 0-0.063366 4.583183 1.515280 7 6 0-0.052816 5.159789 0.225233 8 6 0-0.062755 6.526306-0.108988 9 6 0-0.100753 7.113554-1.388698 10 6 0-0.103758 8.498296-1.379122 11 6 0-0.078255 9.062353-0.082825 12 6 0-0.138979 10.408285 0.340566 13 6 0-0.505787 10.882976 1.626176 14 6 0-0.500315 12.260567 1.593419 15 6 0-0.121552 12.664798 0.287365 16 6 0 0.000000 14.009877-0.196104 17 6 0-0.143468 14.529882-1.478997 18 6 0-0.014269 15.936083-1.530736 19 6 0 0.228930 16.491947-0.295972 20 16 0-0.018514 3.897933-1.001881 21 16 0-0.014830 7.783568 1.125155 22 7 0 0.103588 11.529953-0.460108 23 16 0 0.300983 15.308404 0.952386 24 1 0-0.011885 1.288753-2.314701 25 1 0-0.058912 2.602777 2.416921 26 1 0-0.086784 5.180240 2.420246 27 1 0-0.151329 6.526413-2.299616 28 1 0-0.182829 9.090229-2.280804 29 1 0-0.807839 10.257028 2.454945 30 1 0-0.790034 12.933919 2.387822 37

31 1 0-0.387085 13.927629-2.345696 32 1 0-0.106890 16.519420-2.439332 33 6 0 0.780755 11.507417-1.756566 34 1 0 0.066169 11.445724-2.583854 35 1 0 1.369191 12.418953-1.863434 36 1 0 1.457406 10.652692-1.794409 37 6 0 0.011786-1.265689-0.119388 38 6 0 0.005996-0.690539-1.410063 39 6 0 0.026038-2.628710 0.222643 40 6 0 0.048672-3.201866 1.512769 41 6 0 0.063366-4.583183 1.515280 42 6 0 0.052816-5.159789 0.225233 43 6 0 0.062755-6.526306-0.108988 44 6 0 0.100753-7.113554-1.388698 45 6 0 0.103758-8.498296-1.379122 46 6 0 0.078255-9.062353-0.082825 47 6 0 0.138979-10.408285 0.340566 48 6 0 0.505787-10.882976 1.626176 49 6 0 0.500315-12.260567 1.593419 50 6 0 0.121552-12.664798 0.287365 51 6 0 0.000000-14.009877-0.196104 52 6 0 0.143468-14.529882-1.478997 53 6 0 0.014269-15.936083-1.530736 54 6 0-0.228930-16.491947-0.295972 55 16 0 0.018514-3.897933-1.001881 56 16 0 0.014830-7.783568 1.125155 57 7 0-0.103588-11.529953-0.460108 58 16 0-0.300983-15.308404 0.952386 59 1 0 0.011885-1.288753-2.314701 60 1 0 0.058912-2.602777 2.416921 61 1 0 0.086784-5.180240 2.420246 62 1 0 0.151329-6.526413-2.299616 63 1 0 0.182829-9.090229-2.280804 64 1 0 0.807839-10.257028 2.454945 65 1 0 0.790034-12.933919 2.387822 66 1 0 0.387085-13.927629-2.345696 38

67 1 0 0.106890-16.519420-2.439332 68 6 0-0.780755-11.507417-1.756566 69 1 0-0.066169-11.445724-2.583854 70 1 0-1.369191-12.418953-1.863434 71 1 0-1.457406-10.652692-1.794409 72 1 0 0.378163 17.536548-0.055171 73 1 0-0.378163-17.536548-0.055171 E(RB+HF-LYP) = -4360.00383303 hartree Table 13. Cartesian Coordinate of the optimized structure for pin-unrestricted inglet (U) 9TP-C1 at the B3LYP/6-31G(d) level. Center Atomic Atomic Coordinates (Angstroms) Number Number Type X Y Z 1 16 0 0.000000 0.000000 1.085648 2 6 0-0.019557 1.261896-0.136443 3 6 0-0.010550 0.698454-1.414606 4 6 0-0.042414 2.641018 0.225674 5 6 0-0.078478 3.199696 1.507817 6 6 0-0.098900 4.593577 1.514148 7 6 0-0.078575 5.165764 0.236351 8 6 0-0.091171 6.542407-0.109774 9 6 0-0.122895 7.119522-1.388507 10 6 0-0.125209 8.509858-1.383148 11 6 0-0.103103 9.075056-0.093428 12 6 0-0.165241 10.423885 0.331216 13 6 0-0.546092 10.897675 1.615917 14 6 0-0.527956 12.273351 1.587744 15 6 0-0.130093 12.680080 0.285519 16 6 0 0.000000 14.022774-0.191690 17 6 0-0.094002 14.544630-1.481140 18 6 0 0.025885 15.950003-1.525788 19 6 0 0.213489 16.506600-0.280224 20 16 0-0.028470 3.906843-0.991609 39

21 16 0-0.053386 7.796819 1.118762 22 7 0 0.097389 11.541416-0.461785 23 16 0 0.242590 15.323807 0.969696 24 1 0-0.020851 1.293878-2.321071 25 1 0-0.094789 2.599222 2.410707 26 1 0-0.133358 5.184952 2.422748 27 1 0-0.166650 6.528993-2.297197 28 1 0-0.199307 9.097675-2.288321 29 1 0-0.861780 10.270411 2.438378 30 1 0-0.821567 12.946322 2.381175 31 1 0-0.296242 13.942591-2.358239 32 1 0-0.033603 16.534200-2.436568 33 6 0 0.789508 11.513382-1.750544 34 1 0 0.083308 11.472769-2.586178 35 1 0 1.400956 12.411174-1.843189 36 1 0 1.446114 10.643223-1.785714 37 6 0 0.019557-1.261896-0.136443 38 6 0 0.010550-0.698454-1.414606 39 6 0 0.042414-2.641018 0.225674 40 6 0 0.078478-3.199696 1.507817 41 6 0 0.098900-4.593577 1.514148 42 6 0 0.078575-5.165764 0.236351 43 6 0 0.091171-6.542407-0.109774 44 6 0 0.122895-7.119522-1.388507 45 6 0 0.125209-8.509858-1.383148 46 6 0 0.103103-9.075056-0.093428 47 6 0 0.165241-10.423885 0.331216 48 6 0 0.546092-10.897675 1.615917 49 6 0 0.527956-12.273351 1.587744 50 6 0 0.130093-12.680080 0.285519 51 6 0 0.000000-14.022774-0.191690 52 6 0 0.094002-14.544630-1.481140 53 6 0-0.025885-15.950003-1.525788 54 6 0-0.213489-16.506600-0.280224 55 16 0 0.028470-3.906843-0.991609 56 16 0 0.053386-7.796819 1.118762 40

57 7 0-0.097389-11.541416-0.461785 58 16 0-0.242590-15.323807 0.969696 59 1 0 0.020851-1.293878-2.321071 60 1 0 0.094789-2.599222 2.410707 61 1 0 0.133358-5.184952 2.422748 62 1 0 0.166650-6.528993-2.297197 63 1 0 0.199307-9.097675-2.288321 64 1 0 0.861780-10.270411 2.438378 65 1 0 0.821567-12.946322 2.381175 66 1 0 0.296242-13.942591-2.358239 67 1 0 0.033603-16.534200-2.436568 68 6 0-0.789508-11.513382-1.750544 69 1 0-0.083308-11.472769-2.586178 70 1 0-1.400956-12.411174-1.843189 71 1 0-1.446114-10.643223-1.785714 72 1 0 0.344831 17.552280-0.033379 73 1 0-0.344831-17.552280-0.033379 E(UB+HF-LYP) = -4360.00908117 hartree Table 14. Cartesian Coordinate of the optimized structure for Triplet (T) 9TP-C1 at the B3LYP/6-31G(d) level. Center Atomic Atomic Coordinates (Angstroms) Number Number Type X Y Z 1 16 0 0.000000 0.000000 1.073459 2 6 0-0.025632 1.260143-0.146941 3 6 0-0.014169 0.701891-1.419984 4 6 0-0.055074 2.646025 0.224742 5 6 0-0.107844 3.197615 1.503656 6 6 0-0.130195 4.596941 1.512474 7 6 0-0.094420 5.167947 0.240489 8 6 0-0.105544 6.548940-0.110893 9 6 0-0.126288 7.121675-1.389553 10 6 0-0.128324 8.514487-1.386130 41

11 6 0-0.115947 9.080104-0.099246 12 6 0-0.181145 10.430132 0.326212 13 6 0-0.576320 10.902948 1.608085 14 6 0-0.551794 12.277938 1.582903 15 6 0-0.137027 12.686194 0.285477 16 6 0 0.000000 14.027820-0.187558 17 6 0-0.062703 14.551125-1.479683 18 6 0 0.053548 15.955983-1.520007 19 6 0 0.207797 16.512419-0.268987 20 16 0-0.026624 3.910850-0.988112 21 16 0-0.080010 7.801933 1.115113 22 7 0 0.095815 11.545937-0.460954 23 16 0 0.208786 15.329600 0.980730 24 1 0-0.028220 1.296221-2.327125 25 1 0-0.135641 2.595781 2.405242 26 1 0-0.177594 5.185343 2.422523 27 1 0-0.161301 6.529574-2.297427 28 1 0-0.194466 9.100538-2.293225 29 1 0-0.903520 10.274856 2.425298 30 1 0-0.851876 12.950370 2.374428 31 1 0-0.240378 13.949529-2.362227 32 1 0 0.015234 16.541012-2.431380 33 6 0 0.802588 11.515768-1.741821 34 1 0 0.105581 11.485208-2.585531 35 1 0 1.424980 12.407043-1.823708 36 1 0 1.449964 10.638614-1.772369 37 6 0 0.025632-1.260143-0.146941 38 6 0 0.014169-0.701891-1.419984 39 6 0 0.055074-2.646025 0.224742 40 6 0 0.107844-3.197615 1.503656 41 6 0 0.130195-4.596941 1.512474 42 6 0 0.094420-5.167947 0.240489 43 6 0 0.105544-6.548940-0.110893 44 6 0 0.126288-7.121675-1.389553 45 6 0 0.128324-8.514487-1.386130 46 6 0 0.115947-9.080104-0.099246 42

47 6 0 0.181145-10.430132 0.326212 48 6 0 0.576320-10.902948 1.608085 49 6 0 0.551794-12.277938 1.582903 50 6 0 0.137027-12.686194 0.285477 51 6 0 0.000000-14.027820-0.187558 52 6 0 0.062703-14.551125-1.479683 53 6 0-0.053548-15.955983-1.520007 54 6 0-0.207797-16.512419-0.268987 55 16 0 0.026624-3.910850-0.988112 56 16 0 0.080010-7.801933 1.115113 57 7 0-0.095815-11.545937-0.460954 58 16 0-0.208786-15.329600 0.980730 59 1 0 0.028220-1.296221-2.327125 60 1 0 0.135641-2.595781 2.405242 61 1 0 0.177594-5.185343 2.422523 62 1 0 0.161301-6.529574-2.297427 63 1 0 0.194466-9.100538-2.293225 64 1 0 0.903520-10.274856 2.425298 65 1 0 0.851876-12.950370 2.374428 66 1 0 0.240378-13.949529-2.362227 67 1 0-0.015234-16.541012-2.431380 68 6 0-0.802588-11.515768-1.741821 69 1 0-0.105581-11.485208-2.585531 70 1 0-1.424980-12.407043-1.823708 71 1 0-1.449964-10.638614-1.772369 72 1 0 0.329597 17.558460-0.018624 73 1 0-0.329597-17.558460-0.018624 E(UB+HF-LYP) = -4360.00673163 hartree Table 15. Cartesian Coordinate of the optimized structure for pin-restricted inglet (R) Me-6TP 6TP-C1 2+ at the B3LYP/6-31G(d) level. Center Atomic Atomic Coordinates (Angstroms) Number Number Type X Y Z 43

1 6 0-0.165745 0.680274-0.101447 2 6 0-1.456042 1.262172-0.149262 3 6 0-1.456887 2.640273-0.133933 4 6 0-0.160719 3.218687-0.082952 5 16 0 1.059293 1.944586-0.021371 6 6 0 0.242959 4.562581-0.123622 7 6 0 1.543233 5.053369-0.450850 8 6 0 1.497577 6.421847-0.453883 9 6 0 0.165745 6.822324-0.121308 10 7 0-0.575090 5.676155 0.091967 11 6 0-0.322143 8.149790-0.046100 12 6 0-1.626639 8.662578-0.124677 13 6 0-1.695174 10.053128-0.083313 14 6 0-0.440745 10.665294 0.035756 15 16 0 0.834840 9.483596 0.088927 16 6 0 0.165745-0.680274-0.101447 17 6 0 1.456042-1.262172-0.149262 18 6 0 1.456887-2.640273-0.133933 19 6 0 0.160719-3.218687-0.082952 20 16 0-1.059293-1.944586-0.021371 21 6 0-0.242959-4.562581-0.123622 22 6 0-1.543233-5.053369-0.450850 23 6 0-1.497577-6.421847-0.453883 24 6 0-0.165745-6.822324-0.121308 25 7 0 0.575090-5.676155 0.091967 26 6 0 0.322143-8.149790-0.046100 27 6 0 1.626639-8.662578-0.124677 28 6 0 1.695174-10.053128-0.083313 29 6 0 0.440745-10.665294 0.035756 30 16 0-0.834840-9.483596 0.088927 31 6 0-1.877321 5.640863 0.759305 32 1 0-2.360173 0.667599-0.225239 33 1 0-2.362234 3.225523-0.222418 34 1 0 2.387200 4.433908-0.722718 35 1 0 2.296371 7.098187-0.725004 36 1 0-2.503384 8.043181-0.264625 44

37 1 0-2.617631 10.618201-0.152423 38 1 0-2.701092 5.607486 0.038869 39 1 0-1.923926 4.765243 1.407618 40 1 0-1.980633 6.529842 1.382629 41 6 0 1.877321-5.640863 0.759305 42 1 0 2.360173-0.667599-0.225239 43 1 0 2.362234-3.225523-0.222418 44 1 0-2.387200-4.433908-0.722718 45 1 0-2.296371-7.098187-0.725004 46 1 0 2.503384-8.043181-0.264625 47 1 0 2.617631-10.618201-0.152423 48 1 0 2.701092-5.607486 0.038869 49 1 0 1.923926-4.765243 1.407618 50 1 0 1.980633-6.529842 1.382629 51 16 0-0.222718 12.378313 0.137053 52 6 0 1.591204 12.574952 0.219147 53 1 0 2.068705 12.172928-0.678012 54 1 0 1.994561 12.109873 1.122168 55 1 0 1.764029 13.652433 0.264471 56 16 0 0.222718-12.378313 0.137053 57 6 0-1.591204-12.574952 0.219147 58 1 0-2.068705-12.172928-0.678012 59 1 0-1.764029-13.652433 0.264471 60 1 0-1.994561-12.109873 1.122168 E(RB+HF-LYP) = -3579.54203243 hartree Table 16. Cartesian Coordinate of the optimized structure for pin-unrestricted inglet (U) Me-6TP 6TP-C1 at the B3LYP/6-31G(d) level. Center Atomic Atomic Coordinates (Angstroms) Number Number Type X Y Z 1 6 0-0.149654 0.695414-0.192368 2 6 0-1.406340 1.311717-0.255995 3 6 0-1.355391 2.703533-0.238622 45

4 6 0-0.051425 3.222442-0.166865 5 16 0 1.116583 1.907030-0.093754 6 6 0 0.415391 4.562943-0.206378 7 6 0 1.714191 5.002186-0.584317 8 6 0 1.729344 6.375174-0.542011 9 6 0 0.437410 6.819879-0.134792 10 7 0-0.342835 5.692824 0.079411 11 6 0 0.006460 8.162207-0.002226 12 6 0-1.280460 8.727157 0.009836 13 6 0-1.290404 10.116588 0.088476 14 6 0-0.006460 10.677685 0.146515 15 16 0 1.222682 9.445258 0.098309 16 6 0 0.149654-0.695414-0.192368 17 6 0 1.406340-1.311717-0.255995 18 6 0 1.355391-2.703533-0.238622 19 6 0 0.051425-3.222442-0.166865 20 16 0-1.116583-1.907030-0.093754 21 6 0-0.415391-4.562943-0.206378 22 6 0-1.714191-5.002186-0.584317 23 6 0-1.729344-6.375174-0.542011 24 6 0-0.437410-6.819879-0.134792 25 7 0 0.342835-5.692824 0.079411 26 6 0-0.006460-8.162207-0.002226 27 6 0 1.280460-8.727157 0.009836 28 6 0 1.290404-10.116588 0.088476 29 6 0 0.006460-10.677685 0.146515 30 16 0-1.222682-9.445258 0.098309 31 6 0-1.622072 5.685333 0.790756 32 1 0-2.331642 0.752632-0.343525 33 1 0-2.237747 3.321881-0.339759 34 1 0 2.514699 4.354789-0.915027 35 1 0 2.544679 7.023864-0.831377 36 1 0-2.187322 8.145193-0.090944 37 1 0-2.191899 10.718674 0.087734 38 1 0-2.469192 5.734388 0.098932 39 1 0-1.693661 4.775043 1.386594 46

40 1 0-1.658198 6.539521 1.467893 41 6 0 1.622072-5.685333 0.790756 42 1 0 2.331642-0.752632-0.343525 43 1 0 2.237747-3.321881-0.339759 44 1 0-2.514699-4.354789-0.915027 45 1 0-2.544679-7.023864-0.831377 46 1 0 2.187322-8.145193-0.090944 47 1 0 2.191899-10.718674 0.087734 48 1 0 2.469192-5.734388 0.098932 49 1 0 1.693661-4.775043 1.386594 50 1 0 1.658198-6.539521 1.467893 51 16 0 0.282222 12.376246 0.270213 52 6 0 2.104084 12.506860 0.251231 53 1 0 2.513168 12.109133-0.680875 54 1 0 2.540450 12.006160 1.119080 55 1 0 2.318463 13.576195 0.309666 56 16 0-0.282222-12.376246 0.270213 57 6 0-2.104084-12.506860 0.251231 58 1 0-2.513168-12.109133-0.680875 59 1 0-2.318463-13.576195 0.309666 60 1 0-2.540450-12.006160 1.119080 E(UB+HF-LYP) = -3579.54470690 hartree Table 17. Cartesian Coordinate of the optimized structure for Triplet (T) Me-6TP 6TP-C1 at the B3LYP/6-31G(d) level. Center Atomic Atomic Coordinates (Angstroms) Number Number Type X Y Z 1 6 0-0.160570 0.702455-0.318472 2 6 0-1.410563 1.303158-0.404739 3 6 0-1.365097 2.707366-0.382847 4 6 0-0.074500 3.222011-0.281671 5 16 0 1.095704 1.913895-0.194101 6 6 0 0.397266 4.575598-0.309738 47

7 6 0 1.671717 5.024268-0.740303 8 6 0 1.693839 6.397763-0.640443 9 6 0 0.429164 6.825670-0.149862 10 7 0-0.342629 5.684681 0.058840 11 6 0 0.003807 8.160357 0.053501 12 6 0-1.282044 8.719981 0.169718 13 6 0-1.288882 10.104886 0.295918 14 6 0-0.003807 10.669775 0.288321 15 16 0 1.222682 9.443376 0.119900 16 6 0 0.160570-0.702455-0.318472 17 6 0 1.410563-1.303158-0.404739 18 6 0 1.365097-2.707366-0.382847 19 6 0 0.074500-3.222011-0.281671 20 16 0-1.095704-1.913895-0.194101 21 6 0-0.397266-4.575598-0.309738 22 6 0-1.671717-5.024268-0.740303 23 6 0-1.693839-6.397763-0.640443 24 6 0-0.429164-6.825670-0.149862 25 7 0 0.342629-5.684681 0.058840 26 6 0-0.003807-8.160357 0.053501 27 6 0 1.282044-8.719981 0.169718 28 6 0 1.288882-10.104886 0.295918 29 6 0 0.003807-10.669775 0.288321 30 16 0-1.222682-9.443376 0.119900 31 6 0-1.594541 5.644709 0.816347 32 1 0-2.332380 0.741496-0.509417 33 1 0-2.247699 3.323724-0.498922 34 1 0 2.450748 4.388328-1.137094 35 1 0 2.496482 7.055832-0.944189 36 1 0-2.191963 8.137684 0.110838 37 1 0-2.189479 10.703244 0.375094 38 1 0-2.464958 5.757578 0.162024 39 1 0-1.661504 4.691735 1.341352 40 1 0-1.590392 6.445112 1.557312 41 6 0 1.594541-5.644709 0.816347 42 1 0 2.332380-0.741496-0.509417 48