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

Kant, R.; Gupta, V.K.; Kapoor, K.; Deshmukh, M.B.; Patil, D.R.; Anbhule, P.V.

doi:10.1107/S160053681204202X

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 (C-C) = 0.003 Å
R = 0.046
wR = 0.133
Data-to-parameter ratio = 15.1
Details

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

Rajni Kant,^a ^* Vivek K. Gupta,^a Kamini Kapoor,^a Madhukar B. Deshmukh,^b D. R. Patil ^b and P. V. Anbhule ^b

^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-HO interactions into chains along the b axis.

Related literature

For the synthesis and pharmaceutical activity of enaminones, see: Kantevari et al. (2007); Ke et al. (2009); Omran et al. (1997); Eddington et al. (2003). For a related structure, see: Deng et al. (2010).

Experimental

Crystal data

C₁₁H₁₂FNO
M_r = 193.22
Monoclinic, P 2₁ /c
a = 13.2832 (6) Å
b = 5.8530 (2) Å
c = 14.2995 (8) Å
= 116.086 (6)°
V = 998.49 (8) Å³
Z = 4
Mo K radiation
= 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 $[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ ) T_min = 0.824, T_max = 1.000
14183 measured reflections
1952 independent reflections
1430 reflections with I > 2(I)
R_int = 0.040

Refinement

R[F² > 2(F²)] = 0.046
wR(F²) = 0.133
S = 1.04
1952 reflections
129 parameters
H-atom parameters constrained
_max = 0.20 e Å^-3
_min = -0.16 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C6-H6BO1ⁱ	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); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: PLATON (Spek, 2009).

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.
Eddington, N. D., Cox, S. D. & Khurana, M. (2003). Eur. J. Med. Chem. 38, 49-64.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Kantevari, S., Chary, M. V. & Vuppalapati, S. V. N. (2007). Tetrahedron, 63, 13024-13031.
Ke, Y. Y., Li, Y. J. & Jia, J. H. (2009). Tetrahedron Lett. 50, 1389-1391.
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.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.

organic compounds