Helical assembly formed by chiral [11]thiaheterohelicene molecules in crystals. Architecture with triple helix

Chemistry Letters

Volumn 32, Issue 1, 2003, Pages 90-91

  Nakagawa, Hiroko ^a   Yoshino, Jun ^a   Yamada, Koh Ichi ^a   Shiro, Motoo ^b  

^a JOSAI UNIVERSITY   (Japan)

^b RIGAKU CORPORATION   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE DERIVATIVE; THIAHETEROHELICENE; UNCLASSIFIED DRUG;

ARTICLE; CHIRALITY; CRYSTAL STRUCTURE; CRYSTALLOGRAPHY; ENANTIOMER; MOLECULAR BIOLOGY; RACEMIC MIXTURE;

EID: 0037419589     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.2003.90     Document Type: Article

References (18)

1. L. Brunsveld, E. W. Meijer, R. B. Prince, and J. S. Moore, J. Am. Chem. Soc., 123, 7978 (2001).
2. For example: R. Kuroda, J. Chem. Soc., Perkin Trans. 2, 1982, 789; S. Ramdas and J. M. Thomas, J. Phys. Chem., 85, 2421 (1981); B. S. Green and M. Knossow, Science, 214, 795 (1981); G. Le Bas, A. Navaza, M. Knossow, and C. de Rango, Cryst. Struct. Commun., 5, 713 (1976).
3. For example: R. Kuroda, J. Chem. Soc., Perkin Trans. 2, 1982, 789; S. Ramdas and J. M. Thomas, J. Phys. Chem., 85, 2421 (1981); B. S. Green and M. Knossow, Science, 214, 795 (1981); G. Le Bas, A. Navaza, M. Knossow, and C. de Rango, Cryst. Struct. Commun., 5, 713 (1976).
4. For example: R. Kuroda, J. Chem. Soc., Perkin Trans. 2, 1982, 789; S. Ramdas and J. M. Thomas, J. Phys. Chem., 85, 2421 (1981); B. S. Green and M. Knossow, Science, 214, 795 (1981); G. Le Bas, A. Navaza, M. Knossow, and C. de Rango, Cryst. Struct. Commun., 5, 713 (1976).
5. For example: R. Kuroda, J. Chem. Soc., Perkin Trans. 2, 1982, 789; S. Ramdas and J. M. Thomas, J. Phys. Chem., 85, 2421 (1981); B. S. Green and M. Knossow, Science, 214, 795 (1981); G. Le Bas, A. Navaza, M. Knossow, and C. de Rango, Cryst. Struct. Commun., 5, 713 (1976).
6. For example: K. Tanaka, H. Osuga, and Y. Kitahara, J. Chem. Soc., Perkin Trans. 2, 2000, 2492; H. Nakagawa, A. Obata, K. Yamada, H. Kawazura, M. Konno, and H. Miyamae, J. Chem. Soc., Perkin Trans. 2, 1985, 1899; H. Nakagawa, K. Yamada, H. Kawazura, and H. Miyamae, Acta Crystallogr., C40, 1039 (1984); H. Nakagawa, H. Nagashima, K. Yamada, and H. Kawazura, Acta Crystallogr., C41, 778 (1985).
7. For example: K. Tanaka, H. Osuga, and Y. Kitahara, J. Chem. Soc., Perkin Trans. 2, 2000, 2492; H. Nakagawa, A. Obata, K. Yamada, H. Kawazura, M. Konno, and H. Miyamae, J. Chem. Soc., Perkin Trans. 2, 1985, 1899; H. Nakagawa, K. Yamada, H. Kawazura, and H. Miyamae, Acta Crystallogr., C40, 1039 (1984); H. Nakagawa, H. Nagashima, K. Yamada, and H. Kawazura, Acta Crystallogr., C41, 778 (1985).
8. For example: K. Tanaka, H. Osuga, and Y. Kitahara, J. Chem. Soc., Perkin Trans. 2, 2000, 2492; H. Nakagawa, A. Obata, K. Yamada, H. Kawazura, M. Konno, and H. Miyamae, J. Chem. Soc., Perkin Trans. 2, 1985, 1899; H. Nakagawa, K. Yamada, H. Kawazura, and H. Miyamae, Acta Crystallogr., C40, 1039 (1984); H. Nakagawa, H. Nagashima, K. Yamada, and H. Kawazura, Acta Crystallogr., C41, 778 (1985).
9. For example: K. Tanaka, H. Osuga, and Y. Kitahara, J. Chem. Soc., Perkin Trans. 2, 2000, 2492; H. Nakagawa, A. Obata, K. Yamada, H. Kawazura, M. Konno, and H. Miyamae, J. Chem. Soc., Perkin Trans. 2, 1985, 1899; H. Nakagawa, K. Yamada, H. Kawazura, and H. Miyamae, Acta Crystallogr., C40, 1039 (1984); H. Nakagawa, H. Nagashima, K. Yamada, and H. Kawazura, Acta Crystallogr., C41, 778 (1985).
10. IUPAC Name: bisthieno[3″, 2″: 4′, 5′][1]benzothieno-[3′, 2′: 4, 5]benzo[1,2-b: 4, 3-b']di[1]benzothiophene. Synthesis: K. Yamada, S. Ogashiwa, H. Tanaka, H. Nakagawa, and H. Kawazura, Chem. Lett., 1981, 343; Optical resolution: H. Nakagawa, S. Ogashiwa, H. Tanaka, K. Yamada, and H. Kawazura, Bull. Chem. Soc. Jpn., 54, 1903 (1981).
11. IUPAC Name: bisthieno[3″, 2″: 4′, 5′][1]benzothieno-[3′, 2′: 4, 5]benzo[1,2-b: 4, 3-b']di[1]benzothiophene. Synthesis: K. Yamada, S. Ogashiwa, H. Tanaka, H. Nakagawa, and H. Kawazura, Chem. Lett., 1981, 343; Optical resolution: H. Nakagawa, S. Ogashiwa, H. Tanaka, K. Yamada, and H. Kawazura, Bull. Chem. Soc. Jpn., 54, 1903 (1981).
12. Chirality of the heterohelicenes used here was determined by measurements of CD spectra. K. Yamada, H. Tanaka, H. Nakagawa, S. Ogashiwa, and H. Kawazura, Bull. Chem. Soc. Jpn., 55, 500 (1982).
13. 2 =0.031, Flack parameter = 0.00(5).
14. R. H. Martin, Angew. Chem., Int. Ed. Engl., 13, 649 (1974).
15. IUPAC Name: bis[1]benzothieno[5′, 4′: 2, 3]thieno[3, 2-e: 4, 5-e′]di[1]benzothiophene. The references for synthesis and optical resolution are the same as ref. 4.
16. 2 = 0.096.
17. 2 = 0.038, Flack parameter = -0.0(1). Crystallographic data have been deposited with Cambridge Crystallographic Data Center as supplementary publication no.: (P)11TH CCDC-185521, 11TH racemate CCDC-185523 and (P)9TH CCDC-185522.
18. The number of three has been reported for [7]helicene, which gives no helical assembly in crystals. Th. E. M. van den Hark and P. T. Beurskens, Cryst. Struct. Commun., 5, 247 (1976).