(2E)-1-Phenyl-2-[1-(2-phenyl­prop-2-en-1-yl)pyrrolidin-2-yl­idene]ethanone

Madeley, L.G.; Morgans, G.L.; Lemmerer, A.; Michael, J.P.

doi:10.1107/S1600536812044443

Volume 68
Part 12
Page o3281
December 2012

Received 17 October 2012
Accepted 26 October 2012
Online 3 November 2012

Key indicators
Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.007 Å
R = 0.044
wR = 0.119
Data-to-parameter ratio = 7.5
Details

(2E)-1-Phenyl-2-[1-(2-phenylprop-2-en-1-yl)pyrrolidin-2-ylidene]ethanone

Lee G. Madeley,^a Garreth L. Morgans,^a Andreas Lemmerer ^a and Joseph P. Michael ^a ^*

^aMolecular Sciences Institute, School of Chemistry, University of the Witwatersrand, Private Bag 3, PO WITS, 2050, Johannesburg, South Africa
Correspondence e-mail: joseph.michael@wits.ac.za

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.

Related literature

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).

Experimental

Crystal data

C₂₁H₂₁NO
M_r = 303.39
Triclinic, P 1
a = 5.7806 (6) Å
b = 7.9407 (7) Å
c = 9.6089 (9) Å
= 82.579 (7)°
= 76.793 (7)°
= 83.510 (7)°
V = 424.21 (7) Å³
Z = 1
Mo K radiation
= 0.07 mm^-1
T = 293 K
0.4 × 0.2 × 0.19 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
5222 measured reflections
1563 independent reflections
970 reflections with I > 2(I)
R_int = 0.040

Refinement

R[F² > 2(F²)] = 0.044
wR(F²) = 0.119
S = 0.98
1563 reflections
208 parameters
3 restraints
H-atom parameters constrained
_max = 0.11 e Å^-3
_min = -0.13 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C3-H3O1ⁱ	0.93	2.45	3.368 (5)	170
Symmetry code: (i) x, y+1, z.

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 ).

Acknowledgements

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.

References

Brandenburg, K. (1999). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Bruker (2004). SAINT-Plus and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker (2005). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.
Lemmerer, A., Michael, J. P., Pienaar, D. P. & Sannasy, D. (2007). Acta Cryst. E63, o98-o99.
Michael, J. P., de Koning, C. B., Gravestock, D., Hosken, G. D., Howard, A. S., Jungmann, C. M., Krause, R. W. M., Parsons, A. S., Pelly, S. C. & Stanbury, T. V. (1999). Pure Appl. Chem. 71, 979-988.
Roth, M., Dubs, P., Götschi, E. & Eschenmoser, A. (1971). Helv. Chim. Acta, 54, 710-734.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.

organic compounds