Received 18 March 2013
In the title compound, C6H10N2OS, the 2-sulfanylideneimidazolidin-4-one fragment is essentially planar (r.m.s. deviation = 0.0033 Å). In the crystal, one amino group is involved in N-HO hydrogen bonding, which links pairs of molecules into inversion dimers, while the other amino group generates weak N-HS hydrogen bonds, which link these dimers into chains in [10-1]. The chains are further aggregated into layers parallel to the ac plane through weak C-HO interactions.
For the biological activity of 2-thiohydantoin derivatives, see: Ghoneim et al. (1987); Marton et al. (1993). For the crystal structures of related compounds, see: Kunimoto et al. (2009); Ogawa et al. (2007). For details of the synthesis, see: Wang et al. (2006).
Data collection: APEX2 (Bruker, 2010); cell refinement: SAINT (Bruker, 2010); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: WinGX (Farrugia, 2012).
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CV5395 ).
This work includes part of the activities developed by the Network of Studies and the Development of Novel Inhibitors of Urease, financed by CNPq (562479/2010-4) and FAPEMIG (APQ-04781-10). The authors are also grateful to CNPq (TOB) and CAPES (RPC) for providing their respective fellowships.
Bruker (2010). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.
Ghoneim, K. M., El-Telbany, F. & Ismail, M. A. (1987). Egypt. J. Pharm. Sci. 28, 77-86.
Kunimoto, K.-K., Ichitani, M., Ogawa, T., Kitoh, S.-I., Kuwae, A. & Hanai, K. (2009). Spectrosc. Lett. 42, 73-80.
Marton, J., Enisz, J., Hosztafi, S. & Timar, T. (1993). J. Agric. Food Chem. 41, 148-152.
Ogawa, T., Kitoh, S.-I., Ichitani, M., Kuwae, A., Hanai, K. & Kunimoto, K.-K. (2007). Anal. Sci. X-Ray Struct. Anal. Online, 42, x199-x200.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Wang, Z. D., Sheikh, S. O. & Zhang, Y. (2006). Molecules, 11, 739-750.