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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 [sigma](C-C) = 0.002 Å
R = 0.046
wR = 0.127
Data-to-parameter ratio = 19.2
Details
Open access

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

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-H...N and N-H...O links.

Related literature

For the biological activity of hydantoin derivatives and their metal complexes, see: Rajic et al. (2006[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.]); Bazil et al. (1998[Bazil, C. & Pedley, T. (1998). Annu. Rev. Med. 49, 135-162.]); Bakalova et al. (2005[Bakalova, A., Buyukliev, R., Momekov, G., Ivanov, D., Todorov, D., Konstantinov, S. & Karaivanova, M. (2005). Eur. J. Med. Chem. 40, 590-596.], 2008[Bakalova, A., Varbanov, H., Buyukliev, R., Momekov, G., Ferdinandov, D., Konstantinov, S. & Ivanov, D. (2008). Eur. J. Med. Chem. 43, 958-965.], 2009[Bakalova, A., Varbanov, H., Buyukliev, R., Momekov, G. & Ivanov, D. (2009). J. Therm. Anal. Calorim. 95, 241-246.]). For crystal structures of other 3-amino substituted hydantoins and their metal complexes, see: Shivachev et al. (2005[Shivachev, B., Petrova, R. & Naydenova, E. (2005). Acta Cryst. C61, o524-o526.]); Bakalova et al. (2007[Bakalova, A., Petrova, R., Shivatchev, B. & Varbanov, H. (2007). J. Coord. Chem. 60, 1701-1707.]). For the synthesis of 5-methyl-5-(4-pyridyl)-hydantoin, see: Chu & Teague (1958[Chu, C.-C. & Teague, P. C. (1958). J. Org. Chem. 23, 1578.]). For the preparation of 3-aminohydantoins, see: Davidson (1964[Davidson, J. (1964). J. Chem. Soc. pp. 4646-4656.]).

[Scheme 1]

Experimental

Crystal data
  • C9H10N4O2

  • Mr = 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[alpha] radiation

  • [mu] = 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[Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.948, Tmax = 0.948

  • 51879 measured reflections

  • 2765 independent reflections

  • 2179 reflections with I > 2[sigma](I)

  • Rint = 0.076

Refinement
  • R[F2 > 2[sigma](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

  • [Delta][rho]max = 0.56 e Å-3

  • [Delta][rho]min = -0.44 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N2-H2...N4i 0.88 2.69 3.526 159
N2-H2...O2i 0.88 2.26 2.9184 (15) 131
N4-H4A...O1ii 0.977 (19) 2.139 (19) 3.0676 (16) 158.07
N4-H4B...O1iii 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[Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2005[Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); 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

Bakalova, A., Buyukliev, R., Momekov, G., Ivanov, D., Todorov, D., Konstantinov, S. & Karaivanova, M. (2005). Eur. J. Med. Chem. 40, 590-596.  [ISI] [CrossRef] [PubMed] [ChemPort]
Bakalova, A., Petrova, R., Shivatchev, B. & Varbanov, H. (2007). J. Coord. Chem. 60, 1701-1707.  [ISI] [CSD] [CrossRef] [ChemPort]
Bakalova, A., Varbanov, H., Buyukliev, R., Momekov, G., Ferdinandov, D., Konstantinov, S. & Ivanov, D. (2008). Eur. J. Med. Chem. 43, 958-965.  [ISI] [CrossRef] [PubMed] [ChemPort]
Bakalova, A., Varbanov, H., Buyukliev, R., Momekov, G. & Ivanov, D. (2009). J. Therm. Anal. Calorim. 95, 241-246.  [ISI] [CrossRef] [ChemPort]
Bazil, C. & Pedley, T. (1998). Annu. Rev. Med. 49, 135-162.  [ISI] [ChemPort] [PubMed]
Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Chu, C.-C. & Teague, P. C. (1958). J. Org. Chem. 23, 1578.  [CrossRef]
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.  [CrossRef] [PubMed] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Shivachev, B., Petrova, R. & Naydenova, E. (2005). Acta Cryst. C61, o524-o526.  [CrossRef] [details]


Acta Cryst (2009). E65, o953  [ doi:10.1107/S1600536809011404 ]

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