Abstract
2,3,5,6-Tetraoxopiperazine (I), ammonium 2,3,5,6-tetraoxo-4-nitropyridinate crystal hydrate (II), co-crystallized dimethylammonium 2,3,5,6-tetraoxo-4-nitropyridinate and dimethylammonium chloride (III), and ammonium 2,6-dioxo-3,5-dinitropyridinate (IV) were isolated in the crystalline state and studied by X-ray diffraction. All heterocycles are planar and nonaromatic. They consist of two conjugated moieties linked together by C-C single bonds. The short C...O contacts (2.841–3.048 Å), which link the molecules to form zigzag two-dimensional chains, make a considerable contribution to the formation of the crystal structure of I, whereas hydrogen bonds that form three-dimensional networks play the most important role in the formation of the crystals of II–IV.
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References
V. I. Minkin, B. Ya. Sinkin, and R. M. Minyaev, Theory of Molecular Structure (Feniks, Rostov-on-Don, 1997) [in Russian].
M. J. S. Dewar, Theory of Molecular Orbitals (McGraw-Hill, New York, 1969; Mir, Moscow, 1972).
C. K. Ingold, Structure and Mechanism in Organic Chemistry (Cornell Univ. Press, Ithaca, N. Y., 1969; Mir, Moscow, 1973).
R. J. Gillespie, Molecular Geometry (Van Nostrand Reinhold, New York, 1972; Mir, Moscow, 1975).
I. B. Bersuker, Electronic Structure and Properties of Coordination Compounds (Khimiya, Leningrad, 1986) [in Russian].
Oxocarbons, Ed. by R. West. Academic, New York, 1980).
G. Seitz and P. Imming, Chem. Rev. 92(6), 1227 (1992).
C. Brunner, Schweigger’s J. 38, 517 (1823).
L. Gmelin, Ann. Phys. (Leipzig) 4, 1 (1825).
A. J. Fatiadi, H. S. Isbell, and W. F. Sager, J. Res. Natl. Bur. Stand. A 67, 153 (1963).
A. J. Kluyver, T. Hof, and A. G. J. Boezaardt, Enzimologia 7, 257 (1939).
J. Liebig, An. Chem. 11, 182 (1934).
E. Weiss and W. Buchner, Helv. Chim. Acta 46, 1121 (1963).
E. Weiss and W. Buchner, Z. Anorg. Allg. Chem. 330, 25 (1964).
E. Weiss and W. Buchner, Chem. Ber. 98, 126 (1965).
O. V. Koval’chukova, S. B. Strashnova, B. E. Zaitsev, et al., Khim. Geterotsikl. Soedin., No. 12, 1690 (1999).
A. Bellamy and P. Golding, Proceedings of New Trends in Research of Energetic Materials (Univ. of Pardubice, Pardubice, Czech Republic, 2008), Part 2, p. 466.
G. M. Sheldrick, Acta Crystallogr. A 64, 12 (2008).
F. H. Allen, C. A. Baalham, J. P. M. Lommerse, and P. R. Raithby, Acta Crystallogr. B 54, 320 (1998).
K. K. Palkina, N. E. Kuz’mina, O. V. Koval’chukova, et al., Dokl. Akad. Nauk 372(6), 768 (2000).
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Original Russian Text © O.V. Kovalchukova, Nguyen Dinh Do, A.I. Stash, S.B. Strashnova, B.E. Zaitsev, 2014, published in Kristallografiya, 2014, Vol. 59, No. 1, pp. 65–70.
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Kovalchukova, O.V., Do, N.D., Stash, A.I. et al. Crystal and molecular structures of selected oxidative nitration products of aminopyrazine and 2-amino-3-hydroxypyridine. Crystallogr. Rep. 59, 60–65 (2014). https://doi.org/10.1134/S1063774513060163
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DOI: https://doi.org/10.1134/S1063774513060163