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Structure of the tetraphenyl borate complex of the indoloquinoline alkaloid cryptolepine

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Abstract

The crystal and molecular structure of the complex, cryptolepine-tetraphenylborate, C16H13N2 +·(C6H5)4B, has been determined by direct methods. The pale yellow crystals are monoclinic, P21/n, a = 11.039(5), b = 16.4918(7), c = 16.404(2) Å, β = 95.70(1)°, V = 2968.75 Å3, and Z = 4. The structure exhibits an unusual form of static disorder with the planar cryptolepine molecules occupying a cleft between tetraphenyl borate molecules. The disorder involves essentially planar cryptolepine molecules packed in one of two orientations in the cleft, related by an almost exact noncrystallographic twofold rotation axis passing through the molecules. The tetraphenyl borate cation, on the other hand, shows no disorder. The distribution of bonds around the boron atom is essentially tetrahedral and the four phenyl rings are planar within experimental error.

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References

  1. Clinquart, E.D. Bull. Acad. Med. 1929, 9, 627.

    Google Scholar 

  2. Delvaux, E. J. Pharm. Belg. 1931, 13, 955.

    Google Scholar 

  3. Delvaux, E. J. Pharm. Belg. 1931, 13, 973.

    Google Scholar 

  4. Boye, G.I.; Ampofo, O. In Proceedings of the First International Seminar on Cryptolepine, Boakye-Yiadom K.; Bamgbose S.O.A., Eds.; 1938; University of Kusami: Ghana, p 37.

    Google Scholar 

  5. Wright, C.W.; Phillipson, J.D.; Awe, S.O.; Kirby, G.G.; Warhurst, D.C.; Quentin-Leclercq, J.; Angenot, L. Phytother. Res. 1996, 10, 361.

    Google Scholar 

  6. Raymond-Hamet, C.R. Soc. Biol. 1937, 126, 768.

    Google Scholar 

  7. Raymond-Hamet, C.R. Acad. Sci. Belg. 1938, 207, 1016.

    Google Scholar 

  8. Noamesi, B.K.; Bamgbose, S.O.A. Planta med. 1980, 39, 51.

    Google Scholar 

  9. Noamesi, B.K.; Bamgbose, S.O.A. Planta Med. 1982, 44, 241.

    Google Scholar 

  10. Rauwald, H.W.; Kober, M.; Mutschler, E.; Lambrecht, G. Planta Med. 1992, 58, 486.

    Google Scholar 

  11. Bamgbose, S.O.A.; Noamesi, B.K. Planta Med. 1981, 41, 392.

    Google Scholar 

  12. Boakye-Yiadom, K.; Heman-Ackah, S.M. J. Pharm. Sci. 1979, 68, 1510.

    Google Scholar 

  13. Paulo, A.; Pimemtel, M.; Veigas, S.; Pires, I.; Duarte, A.; Cabrita, J.; Gomes, E.T. J. Ethnopharmacol. 1994, 44, 73.

    Google Scholar 

  14. Paulo, A.; Duarte, A.; Gomes, E.T. J. Ethnopharmacol. 1994, 44, 127.

    Google Scholar 

  15. Chimanya, K.; De Bruyne, T.; Lasure, A.; Van Poel, B.; Pieters, L.; Claeys, M.; Vanden Berghe, D.; Kambu, K.; Tona, L.; Vlietinck, A.J. Planta Med. 1996, 62, 22.

    Google Scholar 

  16. Bonjean, K.; De Pauw-Gillet, M.C.; Defresne, M.P.; Colson, P.; Houssier, C.; Dassonneville, L.; Bailly, C.; Greimers, R.; Wright C.; Quetin-Leclercq, J.; Tits, M.; Angenot, L. Biochemistry 1998, 37, 5136.

    Google Scholar 

  17. Wright, C.W.; Addae-Kyereme, J.; Brown, J.E.; Tranter, D.A. J. Pharm. Pharmac. 1997, 49, p 36.

    Google Scholar 

  18. Sheldrick, G.M. SHELX86. Program for Solution of Crystal Structures; University of Gottingen: Germany, 1986.

    Google Scholar 

  19. Sheldrick, G.M. SHELXL93. Program for Solution of Crystal Structures; University of Gottingen: Germany, 1993.

    Google Scholar 

  20. Karaulov, A. SNOOPI: Molecular Plotting Program; University of Wales, Cardiff, Wales, 1992.

    Google Scholar 

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Wright, C., Philpson, J., Lisgarten, J. et al. Structure of the tetraphenyl borate complex of the indoloquinoline alkaloid cryptolepine. Journal of Chemical Crystallography 29, 449–455 (1999). https://doi.org/10.1023/A:1009519211938

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  • DOI: https://doi.org/10.1023/A:1009519211938

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