3-Amino-5-methyl-5-(4-pyrid­yl)hydantoin

Varbanov, H.; Buyukliev, R.; Bakalova, A.; Roller, A.

doi:10.1107/S1600536809011404

Volume 65
Part 5
Page o953
May 2009

Received 23 March 2009
Accepted 27 March 2009
Online 2 April 2009

Key indicators
Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.002 Å
R = 0.046
wR = 0.127
Data-to-parameter ratio = 19.2
Details

3-Amino-5-methyl-5-(4-pyridyl)hydantoin

Hristo Varbanov,^a ^* Rossen Buyukliev,^b Adriana Bakalova ^c and Alexander Roller ^a

^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: hristo.varbanov@univie.ac.at

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.

Related literature

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).

Experimental

Crystal data

C₉H₁₀N₄O₂
M_r = 206.21
Tetragonal, I 4₁ /a
a = 12.8282 (5) Å
c = 22.9016 (17) Å
V = 3768.8 (3) Å³
Z = 16
Mo K radiation
= 0.11 mm^-1
T = 100 K
0.50 × 0.50 × 0.50 mm

Data collection

Bruker X8 APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005) T_min = 0.948, T_max = 0.948
51879 measured reflections
2765 independent reflections
2179 reflections with I > 2(I)
R_int = 0.076

Refinement

R[F² > 2(F²)] = 0.046
wR(F²) = 0.127
S = 1.03
2765 reflections
144 parameters
H atoms treated by a mixture of independent and constrained refinement
_max = 0.56 e Å^-3
_min = -0.44 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N2-H2N4ⁱ	0.88	2.69	3.526	159
N2-H2O2ⁱ	0.88	2.26	2.9184 (15)	131
N4-H4AO1ⁱⁱ	0.977 (19)	2.139 (19)	3.0676 (16)	158.07
N4-H4BO1ⁱⁱⁱ	0.96 (2)	2.17 (2)	3.1003 (16)	162.23
Symmetry codes: (i) $[-y+{\script{5\over 4}}, x-{\script{1\over 4}}, z-{\script{1\over 4}}]$ ; (ii) $[y-{\script{1\over 4}}, -x+{\script{5\over 4}}, -z+{\script{1\over 4}}]$ ; (iii) $[-y+{\script{5\over 4}}, x+{\script{1\over 4}}, -z+{\script{1\over 4}}]$ .

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 ).

Acknowledgements

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.

References

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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.
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Chu, C.-C. & Teague, P. C. (1958). J. Org. Chem. 23, 1578.
Davidson, J. (1964). J. Chem. Soc. pp. 4646-4656.
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Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Shivachev, B., Petrova, R. & Naydenova, E. (2005). Acta Cryst. C61, o524-o526.

organic compounds