Received 23 March 2009
aInstitute of Inorganic Chemistry, University of Vienna, Waehringerstrasse 42, A-1090 Vienna, Austria,bDepartment of Organic Chemistry, Faculty of Pharmacy, Medical University - Sofia, 2 Dunav Str., 1000 Sofia, Bulgaria, and cDepartment of Chemistry, Faculty of Pharmacy, Medical University - Sofia, 2 Dunav Str., 1000 Sofia, Bulgaria
Correspondence e-mail: email@example.com
The title compound, 3-amino-5-methyl-5-(4-pyridyl)imidazolidine-2,4-dione, C9H10N4O2, was obtained by reaction of 5-methyl-5-(4-pyridyl)hydantoin with hydrazine. It crystallizes as a racemate in the tetragonal space group I41/a with one molecule in the asymmetric unit. The dihedral angle between the pyridine ring and the five-membered hydantoin ring is 47.99 (3)° In the crystal structure, molecules are joined in a three-dimensional hydrogen-bonded network by N-HN and N-HO links.
For the biological activity of hydantoin derivatives and their metal complexes, see: Rajic et al. (2006); Bazil et al. (1998); Bakalova et al. (2005, 2008, 2009). For crystal structures of other 3-amino substituted hydantoins and their metal complexes, see: Shivachev et al. (2005); Bakalova et al. (2007). For the synthesis of 5-methyl-5-(4-pyridyl)-hydantoin, see: Chu & Teague (1958). For the preparation of 3-aminohydantoins, see: Davidson (1964).
Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: AT2752 ).
The authors are indebted to Professor V. Arion of the Institute of Inorganic Chemistry of the University of Vienna for discussions about the X-ray data.
Bakalova, A., Buyukliev, R., Momekov, G., Ivanov, D., Todorov, D., Konstantinov, S. & Karaivanova, M. (2005). Eur. J. Med. Chem. 40, 590-596.
Bakalova, A., Petrova, R., Shivatchev, B. & Varbanov, H. (2007). J. Coord. Chem. 60, 1701-1707.
Bakalova, A., Varbanov, H., Buyukliev, R., Momekov, G., Ferdinandov, D., Konstantinov, S. & Ivanov, D. (2008). Eur. J. Med. Chem. 43, 958-965.
Bakalova, A., Varbanov, H., Buyukliev, R., Momekov, G. & Ivanov, D. (2009). J. Therm. Anal. Calorim. 95, 241-246.
Bazil, C. & Pedley, T. (1998). Annu. Rev. Med. 49, 135-162.
Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Chu, C.-C. & Teague, P. C. (1958). J. Org. Chem. 23, 1578.
Davidson, J. (1964). J. Chem. Soc. pp. 4646-4656.
Rajic, Z., Zorc, B., Raic-Malic, S., Ester, K., Kralij, M., Pavelic, K., Balzarini, J., De Clercq, E. & Mintas, M. (2006). Molecules, 11, 837-848.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Shivachev, B., Petrova, R. & Naydenova, E. (2005). Acta Cryst. C61, o524-o526.