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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 [sigma](C-C) = 0.007 Å
R = 0.044
wR = 0.119
Data-to-parameter ratio = 7.5
Details
Open access

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

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-H...O 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[Roth, M., Dubs, P., Götschi, E. & Eschenmoser, A. (1971). Helv. Chim. Acta, 54, 710-734.]). For applications of enaminones in alkaloid synthesis, see: Michael et al. (1999[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.]). For a related enaminone structure, see: Lemmerer et al. (2007[Lemmerer, A., Michael, J. P., Pienaar, D. P. & Sannasy, D. (2007). Acta Cryst. E63, o98-o99.]).

[Scheme 1]

Experimental

Crystal data
  • C21H21NO

  • Mr = 303.39

  • Triclinic, P 1

  • a = 5.7806 (6) Å

  • b = 7.9407 (7) Å

  • c = 9.6089 (9) Å

  • [alpha] = 82.579 (7)°

  • [beta] = 76.793 (7)°

  • [gamma] = 83.510 (7)°

  • V = 424.21 (7) Å3

  • Z = 1

  • Mo K[alpha] radiation

  • [mu] = 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[sigma](I)

  • Rint = 0.040

Refinement
  • R[F2 > 2[sigma](F2)] = 0.044

  • wR(F2) = 0.119

  • S = 0.98

  • 1563 reflections

  • 208 parameters

  • 3 restraints

  • H-atom parameters constrained

  • [Delta][rho]max = 0.11 e Å-3

  • [Delta][rho]min = -0.13 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C3-H3...O1i 0.93 2.45 3.368 (5) 170
Symmetry code: (i) x, y+1, z.

Data collection: APEX2 (Bruker, 2005[Bruker (2005). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT-Plus (Bruker, 2004[Bruker (2004). SAINT-Plus and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT-Plus and XPREP (Bruker, 2004[Bruker (2004). SAINT-Plus and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.]); 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: ORTEP-3 for Windows (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]) and DIAMOND (Brandenburg, 1999[Brandenburg, K. (1999). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: WinGX (Farrugia, 1999[Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.]) and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).


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.  [CrossRef] [details]
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.  [CrossRef] [ChemPort] [details]
Lemmerer, A., Michael, J. P., Pienaar, D. P. & Sannasy, D. (2007). Acta Cryst. E63, o98-o99.  [CSD] [CrossRef] [details]
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.  [ISI] [CrossRef] [ChemPort]
Roth, M., Dubs, P., Götschi, E. & Eschenmoser, A. (1971). Helv. Chim. Acta, 54, 710-734.  [CrossRef] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]


Acta Cryst (2012). E68, o3281  [ doi:10.1107/S1600536812044443 ]

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