[Journal logo]

Volume 68 
Part 11 
Page o3110  
November 2012  

Received 13 September 2012
Accepted 8 October 2012
Online 13 October 2012

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.003 Å
R = 0.046
wR = 0.133
Data-to-parameter ratio = 15.1
Details
Open access

(2E)-3-(Dimethylamino)-1-(4-fluorophenyl)prop-2-en-1-one

aX-ray Crystallography Laboratory, Post-Graduate Department of Physics & Electronics, University of Jammu, Jammu Tawi 180 006, India, and bDepartment of Chemistry, Shivaji University, Kolhapur 416 004, India
Correspondence e-mail: rkvk.paper11@gmail.com

In the title compound, C11H12FNO, the dihedral angle between the prop-2-en-1-one group and the benzene ring is 19.33 (6)°. The configuration of the keto group with respect to the olefinic double bond is s-cis. In the crystal, the molecules form dimers through aromatic [pi]-[pi] stacking interactions [centroid-centroid distance = 3.667 (1) Å] and are linked via C-H...O interactions into chains along the b axis.

Related literature

For the synthesis and pharmaceutical activity of enaminones, see: Kantevari et al. (2007[Kantevari, S., Chary, M. V. & Vuppalapati, S. V. N. (2007). Tetrahedron, 63, 13024-13031.]); Ke et al. (2009[Ke, Y. Y., Li, Y. J. & Jia, J. H. (2009). Tetrahedron Lett. 50, 1389-1391.]); Omran et al. (1997[Omran, F. A., Awadi, N. A., Khair, A. A. E. & Elnagdi, M. H. (1997). Org. Prep. Proced. Int. 65, 285-292.]); Eddington et al. (2003[Eddington, N. D., Cox, S. D. & Khurana, M. (2003). Eur. J. Med. Chem. 38, 49-64.]). For a related structure, see: Deng et al. (2010[Deng, J., Shen, D. & Zhou, Z. (2010). Acta Cryst. E66, o2.]).

[Scheme 1]

Experimental

Crystal data
  • C11H12FNO

  • Mr = 193.22

  • Monoclinic, P 21 /c

  • a = 13.2832 (6) Å

  • b = 5.8530 (2) Å

  • c = 14.2995 (8) Å

  • [beta] = 116.086 (6)°

  • V = 998.49 (8) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.10 mm-1

  • T = 293 K

  • 0.3 × 0.2 × 0.2 mm

Data collection
  • Oxford Diffraction Xcalibur Sapphire3 diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]) Tmin = 0.824, Tmax = 1.000

  • 14183 measured reflections

  • 1952 independent reflections

  • 1430 reflections with I > 2[sigma](I)

  • Rint = 0.040

Refinement
  • R[F2 > 2[sigma](F2)] = 0.046

  • wR(F2) = 0.133

  • S = 1.04

  • 1952 reflections

  • 129 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.20 e Å-3

  • [Delta][rho]min = -0.16 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C6-H6B...O1i 0.96 2.59 3.531 (3) 168
Symmetry code: (i) [-x+1, y+{\script{1\over 2}}, -z+{\script{3\over 2}}].

Data collection: CrysAlis PRO (Oxford Diffraction, 2010[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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 (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]); software used to prepare material for publication: 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: GK2520 ).


Acknowledgements

RK acknowledges the Department of Science & Technology for the single-crystal X-ray diffractometer sanctioned as a National Facility under project No. SR/S2/CMP-47/2003. He is also thankful to the University of Jammu, Jammu, India, for financial support.

References

Deng, J., Shen, D. & Zhou, Z. (2010). Acta Cryst. E66, o2.  [CSD] [CrossRef] [details]
Eddington, N. D., Cox, S. D. & Khurana, M. (2003). Eur. J. Med. Chem. 38, 49-64.  [ISI] [CrossRef] [PubMed] [ChemPort]
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  [CrossRef] [details]
Kantevari, S., Chary, M. V. & Vuppalapati, S. V. N. (2007). Tetrahedron, 63, 13024-13031.  [ISI] [CrossRef] [ChemPort]
Ke, Y. Y., Li, Y. J. & Jia, J. H. (2009). Tetrahedron Lett. 50, 1389-1391.  [ISI] [CrossRef] [ChemPort]
Omran, F. A., Awadi, N. A., Khair, A. A. E. & Elnagdi, M. H. (1997). Org. Prep. Proced. Int. 65, 285-292.
Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.
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, o3110  [ doi:10.1107/S160053681204202X ]

This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.