Received 17 October 2012
The title compound, C21H21NO, is a vinylogous amide (enaminone) produced by reaction of 1-(2-phenylprop-2-en-1-yl)pyrrolidine-2-thione with phenacyl bromide. In the molecule, the phenyl rings are twisted from the mean plane of the pyrrolidine ring by 11.2 (1) and 67.3 (1)°. In the crystal, weak C-HO hydrogen bonds link the molecules related by translation along the b axis into chains.
For details of the synthesis of enaminones, see: Roth et al. (1971). For applications of enaminones in alkaloid synthesis, see: Michael et al. (1999). For a related enaminone structure, see: Lemmerer et al. (2007).
Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT-Plus (Bruker, 2004); data reduction: SAINT-Plus and XPREP (Bruker, 2004); 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, 1997) and DIAMOND (Brandenburg, 1999); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2009).
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CV5350 ).
This research was supported by the University of the Witwatersrand and the Molecular Sciences Institute, which are thanked for providing the infrastructure required to do this work.
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