Received 22 October 2010
The title enaminoketone, C12H15NO, is a derivative of 4-(phenylamino)pent-3-en-2-one with an approximately planar pentenone backbone, the greatest displacement from the plane being 0.042 (1) Å; the asymmetry in C-C distances in the group suggests the presence of unsaturated bonds. The dihedral angle between the benzene ring and the pentenone plane is 29.90 (4)°. In the crystal, an intramolecular N-HO interaction and an intermolecular C-HO hydrogen bond are observed.
For synthetic background, see: Shaheen et al. (2006); Venter et al. (2010). For applications of enaminoketones, see: Brink et al. (2010); Chen & Rhodes (1996); Pyzuk et al. (1993); Roodt & Steyn (2000); Tan et al. (2008); Xia et al. (2008). For structures of related ligand systems, see: Venter et al. (2009a,b).
Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT-Plus (Bruker, 2004); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg & Putz, 2005); software used to prepare material for publication: WinGX (Farrugia, 1999).
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: IS2620 ).
Financial assistance from the University of the Free State is gratefully acknowledged. The authors also express their gratitude to SASOL and the South African National Research Foundation (SA-NRF/THRIP) for financial support of this project. Part of this material is based on work supported by the SA-NRF/THRIP under grant No. GUN 2068915. Opinions, findings, conclusions or recommendations expressed in this material are those of the authors and do not necessarily reflect the views of the SA-NRF.
Brandenburg, K. & Putz, H. (2005). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Brink, A., Visser, H. G., Steyl, G. & Roodt, A. (2010). Dalton Trans. pp. 5572-5578.
Bruker (2004). SAINT-Plus and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker (2005). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA.
Chen, H. & Rhodes, J. (1996). J. Mol. Med. 74, 497-504.
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.
Pyzuk, W., Krówczynsk, A. & Górecka, E. (1993). Mol. Cryst. Liq. Cryst. 237, 75-84.
Roodt, A. & Steyn, G. J. J. (2000). Recent Research Developments in Inorganic Chemistry, Vol. 2, pp. 1-23. Trivandrum: Transworld Research Network.
Shaheen, F., Marchio, L., Badshah, A. & Khosa, M. K. (2006). Acta Cryst. E62, o873-o874.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Tan, H. Y., Loke, W. K., Tan, Y. T. & Nguyen, N.-T. (2008). Lab. Chip, 8, 885-891.
Venter, G. J. S., Steyl, G. & Roodt, A. (2009a). Acta Cryst. E65, m1321-m1322.
Venter, G. J. S., Steyl, G. & Roodt, A. (2009b). Acta Cryst. E65, m1606-m1607.
Venter, G. J. S., Steyl, G. & Roodt, A. (2010). Acta Cryst. E66, o1593-o1594.
Xia, M., Wu, B. & Xiang, G. (2008). J. Fluorine Chem. 129, 402-408.