Received 1 October 2013
aA. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 Vavilova St, 119991 Moscow, Russian Federation,bSouth-Russia State Technical University, 346428 Novocherkassk, Russian Federation, and cN. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Prosp, 119991 Moscow, Russian Federation
Correspondence e-mail: email@example.com
The title compound, C7H8N6O, represents the keto form and adopts a nearly planar structure (r.m.s. deviation of the non-H atoms = 0.072 Å). In the crystal, molecules form spiral chains along the c axis by N-HN hydrogen bonds. The chains are linked to each other by weak C-HO hydrogen bonds, forming a three-dimensional framework.
For review on nucleophilic displacement at the 1,2,4,5-tetrazine ring, see: Clavier & Audebert (2010); Tolshchina et al. (2013). For the synthesis of 3-hydroxy-1,2,4,5-tetrazines, see: Ishmetova et al. (2009); Sheremetev et al. (2012a,b). For the structure of 3-hydroxy-1,2,4,5-tetrazine, see: Yeh et al. (1994). For a review on oxo-hydroxy tautomerism of various azines, see: Stanovnik et al. (2006). For standard bond lengths, see: Allen et al. (1987).
Data collection: APEX (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL, PLATON (Spek, 2009) and publCIF (Westrip, 2010).
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: KQ2010 ).
This work was supported financially by the Ministry of Education and Science of Russia through the Federal Target Program "Research and Educational Personnel of Innovative Russia at 2009-2013 Years" (grant No. 14.B37.21.0827), and, in part, by a Russian Foundation for Basic Research (grant No. 12-03-31346).
Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.
Bruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Clavier, G. & Audebert, P. (2010). Chem. Rev. 110, 3299-3314.
Ishmetova, R. I., Latosh, N. I., Ganebnykh, I. N., Ignatenko, N. K., Tolshchina, S. G. & Rusinov, G. L. (2009). Russ. J. Org. Chem. 45, 1102-1107 [translated from (2009). Zh. Org. Khim. 45, 1113-1118].
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Sheremetev, A. B., Palysaeva, N. V., Struchkova, M. I. & Suponitskii, K. Yu. (2012a). Russ. Chem. Bull. 61, 121-130 [translated from (2012). Izv. Akad. Nauk, Ser. Khim. 119-128].
Sheremetev, A. B., Palysaeva, N. V., Struchkova, M. I. & Suponitsky, K. Yu. (2012b). Mendeleev Commun. 22, 302-304.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.
Stanovnik, B., Tisler, M., Katritzky, A. R. & Denisko, O. V. (2006). Adv. Heterocycl. Chem. 91, 1-134.
Tolshchina, S. G., Rusinov, G. L. & Charushin, V. N. (2013). Chem. Heterocycl. Compd, 49, 66-91 [translated from (2013). Khim. Geterotsikl. Soedin. pp. 75-101].
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.
Yeh, M.-Y., Huang, C.-Y., Ueng, C.-H. & Wang, Y. (1994). Acta Cryst. C50, 1781-1784.