Received 25 July 2008
The title compound, C10H9N3O2, was synthesized from azidobenzene and ethyl acetylacetate. A pair of hydrogen bonds [2.617 (2) Å] interconnects a pair of the carboxyl groups, forming an R22(8) inversion dimer, a frequent motif in carboxylic acids. In the title structure, the bonding H atom in the aforementioned O-HO hydrogen bond is significantly shifted towards the acceptor O atom [the donor and acceptor O-H distances are 1.25 (4) and 1.38 (4) Å, respectively]. A plot of the OO versus O-H distances in compounds with paired carboxyl groups shows that the title structure belongs to the group of structures with abnormally long O-H distances with regard to the OO contacts. The displacement of the bonding H atom towards the centre of the hydrogen bond is concomitant with more equal C-O bonding distances in the carboxyl group.
Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL/PC (Sheldrick, 2008); software used to prepare material for publication: SHELXTL/PC.
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: FB2106 ).
This work was supported by a start-up grant from Southeast University to HZ.
Allen, F. H. (2002). Acta Cryst. B58, 380-388.
El Khadem, H., Mansour, H. A. R. & Meshreki, M. H. (1968). J. Chem. Soc. C, pp. 1329-1331.
Etter, M. C., MacDonald, J. & Bernstein, J. (1990). Acta Cryst. B46, 256-262.
Olesen, P. H., Sorensen, A. R., Urso, B., Kurtzhals, P., Bowler, A. N., Ehrbar, U. & Hansen, B. F. (2003). J. Med. Chem. 46, 3333-3341.
Radl, S., Hezky, P., Konvicka, P. & Krejci, J. (2000). Collect. Czech. Chem. Commun. 65, 1093-1108.
Rigaku (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Tian, L., Sun, Y., Li, H., Zheng, X., Cheng, Y., Liu, X. & Qian, B. (2005). J. Inorg. Biochem. 99, 1646-1652.