8568
5. (a) Cheng, C.-C.; Kuo, Y.-N.; Chuang, K.-S.; Luo, C.-F.; Wang, W.-J. Angew. Chem., Int. Ed. Engl. 1999, 38,
1255–1257. (b) Hirai, M.; Shinozuka, K.; Sawai, H.; Ogawa, S. Chem. Lett. 1992, 2023–2026.
6. (a) Ogawa, S.; Yamaguchi, T.; Gotoh, N. J. Chem. Soc., Chem. Commun. 1972, 577–578. (b) Ogawa, S.;
Yamaguchi, T.; Gotoh, N. J. Chem. Soc., Perkin Trans. 1 1974, 976–978.
7. (a) Wang, W.-J.; Yu, T.-M. Synth. Metals 1989, 29, F145–150. (b) Wang, W.-J.; Liao, I.-S. Synth. Metals 1993,
55, 1962–1967. (c) Cotamagna, J.; Canales, J.; Vargas, J.; Alvarado, A.; Ferraudi, G. J. Ind. Chem. 1993, 70,
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1
8. Anal. for H2HAPP·2HCl (C24N6H16Cl2), found (calcd): C, 61.50 (62.74); H, 3.88 (3.49); N, 17.89 (18.30)%. H
NMR (d-TFA) l (ppm): 8.02 (4H, d, J=9.0 Hz), 8.27 (4H, s), 8.93 (4H, d, J=9.0 Hz). FAB-MS (M+1)/z: 387;
IR: 3007, 2768, 1652, 1604, 1578, 1501, 1482, 1470, 1440, 1410, 1362, 1342, 1308, 1260, 1226, 1201, 1144, 1094,
984, 913, 850, 802, 732, 698, 642, 598, 579, 467 cm−1
.
9. Anal. for H2HAPP·H2O (C24N6H16O), found (calcd): C, 71.84 (71.28); H, 3.86 (3.47); N, 20.78 (20.79)%. IR:
3025, 2762, 1642, 1582, 1559, 1531, 1503, 1440, 1420, 1383, 1342, 1317, 1262, 1221, 1198, 1150, 1088, 988, 967,
894, 843, 793, 732, 697, 644, 616, 588, 523, 470 cm−1
.
10. Johnson, C. K. ORTEP II; Report ORNL-5138; Oak Ridge National Laboratory: Oak Ridge, TN, 1976.
11. Crystallographic data and data collection parameters: H2HAPP (2), C24H14N6, M=386; crystal size: 0.40×0.30×
3
,
,
0.15 mm, monoclinic, space group P21/c, a=4.420(1), b=9.988(2), c=19.008(3) A, i=95.47(2)°, V=835.3(3) A ,
Z=2, Dc=1.536 g cm−3, v(Mo-Ka)=0.096 mm−1, F(000)=400, T=298 K. 1669 reflections were measured (1465
unique, Rint=0.0596) on a Siemens P4 diffractometer in the range 1.50<q<25.00°, 0<h<5, 0<k<11, −22<l<22,
,
operating in v scan mode and using graphite-monochromated Mo-Ka radiation (u=0.71073 A). Semi-empirical
absorption correction via 8 scans was applied. Structure solution and refinement: The structure was solved by the
direct method and refined anisotropically based on F2 by full-matrix least-squares techniques using the
SHELXTL (Ver 5.10) program. All hydrogen atoms were located by Fourier synthesis and refined isotropically
without any constraints or restraints. The final refinement gave R1=0.0663, wR2=0.1226. The final difference
−3
,
map showed peaks between 0.216 and −0.231 e A
.
12. Seno, M.; Tsuchiya, S.; Ogawa, S. J. Am. Chem. Soc. 1977, 99, 3014–3018.
13. Nishigaki, S.; Yoshioka, H.; Nakatsu, K. Acta Crystallogr., Sect. B 1978, 34, 875.
14. Hensen, K.; Kettner, M.; Bolte, M. Acta Crystallogr., Sect. C 1998, 54, 359–361.
15. Ansell, C. W. G.; Lewis, J.; Raithby, P. R.; Ramsden, J. N.; Schroder, M. J. Chem. Soc., Chem. Commun. 1982,
546.
16. Cruickshank, D. W. J. Tetrahedron 1962, 17, 155.
.
.