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Structure of adamantan-1-ammonium 1-adamantanecarboxylate

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Abstract

Adamantan-1-ammonium 1-adamantanecarboxylate, C21H33NO2 (I) is a novel dispiro-type compound. Aminoadamantane derivatives, in which the spiro carbon atoms are part of heterocyclic rings, are of potential interest as biological active substances and antiviral agents. Complex (I) crystallizes in the centrosymmetric space group C2/c (No. 15) with eight molecules in the unit cell with a = 25.227(4), b = 6.527(1), c = 22.489(4) Å, and β = 90.75(1)°. The two spiro units are a 1-adamantylammonium cation and a 1-adamantane carbonyloxy anion. The complex units are stabilized by a network of intermolecular carbonyloxy-to-amine hydrogen bonding and van der Waals cohesive forces. Germane bond lengths are: C—N = 1.479(9) and C—O (mean) = 1.25(2) Å.

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References

  1. Hoffmann, C.E. Selective Inhibitors of Viral Functions; Carter, WQ. A., Ed.; CRC Press: Cleveland, OH, 1973, p 199.

    Google Scholar 

  2. Dolin, R.; Reichman, R.C.; Madore, H.P.; Maynard, R.; Lindon, P.M.; Weber-Jones, J. N. Engl. J. Med. 1982, 307, 580.

    Google Scholar 

  3. Bryson, Y.J.; Monahan, C.; Pollack, M.; Shields, W.D. J. Infect. Dis. 1980, 141, 543.

    Google Scholar 

  4. Kolocouris, N.; Foscolos, G.B.; Kolocouris, A.; Marskos, P.; Pouli, N.; Fytas, G.; Ikeda, S.; DeClecq, S. J. Med. Chem. 1994, 37, 2896.

    Google Scholar 

  5. Howells, B.R.; Philips, D.C.; Rogers, D. Acta Crystallogr. 1950, 3, 210.

    Google Scholar 

  6. Gabe, E.J.; LePage, Y.; Charland, J.-P.; Lee, F.L. J. Appl. Crystallogr. 1989, 22,384.

    Google Scholar 

  7. SHELXTL-PC, Siemens Analytical X-ray Instruments, Inc.; Madison, WI, 1989.

  8. Ibers, J.A.; Hamilton, W.C. International Tables for X-ray Crystallography, Vol. IV; Kynoch Press: Birmingham, U.K., 1974.

    Google Scholar 

  9. Orpen, A.G.; Brammer, L.; Allen, F.H.; Kennary, O.; Watson, D.C.; Taylor, R. J. Chem. Soc. Dalton Trans. 1989, S1.

  10. BIDICS, Institute for Material Research; Hamilton, Canada, 1969–1981.

  11. Pauling. L. TheNature of the Chemical Bond, 3rd. Ed.; Cornell University Press: New York, 1960, pp 275, 224.

    Google Scholar 

  12. Hamilton, W.C.; Ibers, J.A. Hydrogen Bonding in Solids; W.A. Benjamin, Inc.: New York, 1968.

    Google Scholar 

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Mullica, D.F., Scott, T.G., Farmer, J.M. et al. Structure of adamantan-1-ammonium 1-adamantanecarboxylate. Journal of Chemical Crystallography 29, 845–848 (1999). https://doi.org/10.1023/A:1009564307821

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