[Journal logo]

Volume 66 
Part 2 
Page o466  
February 2010  

Received 22 January 2010
Accepted 25 January 2010
Online 30 January 2010

[ci5024sup1]
[3d view]

[Cited in]
[Download citation]
Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.002 Å
R = 0.040
wR = 0.115
Data-to-parameter ratio = 18.3
Details
Open access

1-(1-Benzofuran-2-yl)-3-(4-chlorophenyl)prop-2-en-1-one

S. Jeyaseelan,a H. C. Devarajegowda,a* G. Venkatarama,a M. Vinduvahinib and Alphonsus D'souzac

aDepartment of Physics, Yuvaraja's College (Constituent College), University of Mysore, Mysore 570 005, Karnataka, India,bDepartment of Physics, Sri D. Devaraj urs. First Grade College, Hunsur 571 105, Karnataka, India, and cDepartment of Chemistry, St. Philomena's College, Mysore 570 015, Karnataka, India
Correspondence e-mail: devarajegowda@yahoo.com

In the title compound, C17H11ClO2, the benzofuran ring system is almost planar (r.m.s. deviation = 0.011 Å) and forms a dihedral angle of 10.53 (6)° with the chlorophenyl ring. No significant intermolecular interactions are observed.

Related literature

For general background to chalcone, see: Dhar (1981[Dhar, D. N. (1981). In The Chemistry of Chalcones and Related Compounds. New York: John Wiley.]). For the biological properties of benzofuran derivatives, see: Nasef et al. (1992[Nasef, A. M., El-Naem, S. I. & El-Shabrawy, O. A. (1992). Egypt. J. Pharm. Sci. 34, 463-467.]); Bogolyubsakaya & Perovich (1964[Bogolyubsakaya, L. T. & Perovich, M. (1964). Zh. Obshch. Khim. 34, 3119-3122.]); Deshmukh et al. (2004[Deshmukh, M., Kharade, D. & Shirke, S. D. (2004). Monatsh. Chem. 125, 971-976.]); Stanislav et al. (2000[Stanislav, R., Petr, H., Petr, K. & Ivan, K. (2000). Collect. Czech. Chem. Commun. 65, 1093-1108.]); Brady et al. (1973[Brady, B., Kenndey, J. & Sullivan, W. (1973). Tetrahedron, 29, 359-362.]); Kamal et al. (2006[Kamal, M., Hassan, A., Eman, A., Mohey, E. & Hanan, A. (2006). Bioorg. Med. Chem. 14, 3672-3680.]); Alejandro et al. (2008[Alejandro, U., Javier, E., Marcos, R. & Marcela, W. (2008). Molecules, 13, 2385-2393.]); Rajesh et al. (2006[Rajesh, K., Rajendra, P., Mayur, Y., Shanta, K. & Raju, M. (2006). Indian J. Heterocycl. Chem. 15, 245-253.]). For related structures, see: Devarajegowda et al. (2001[Devarajegowda, H. C., Sridhar, M. A., Shashidhara Prasad, J., Indira, J., Sooryanarayanarao, B. & Prakash, P. K. (2001). Mol. Cryst. Liq. Cryst. 369, 145-152.]); Kant et al. (2009[Kant, R., Kamni, Narayana, B., Veena, K. & Yathirajan, H. S. (2009). Acta Cryst. E65, o836.]).

[Scheme 1]

Experimental

Crystal data

  • C17H11ClO2

  • Mr = 282.71

  • Monoclinic, P 21 /c

  • a = 15.9034 (12) Å

  • b = 14.1393 (12) Å

  • c = 5.9572 (5) Å

  • [beta] = 93.039 (4)°

  • V = 1337.67 (19) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.28 mm-1

  • T = 293 K

  • 0.22 × 0.20 × 0.10 mm
Data collection

  • Bruker SMART CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 2004[Sheldrick, G. M. (2004). SADABS. University of Göttingen, Germany.]) Tmin = 0.940, Tmax = 0.972

  • 12871 measured reflections

  • 3323 independent reflections

  • 2665 reflections with I > 2[sigma](I)

  • Rint = 0.026
Refinement

  • R[F2 > 2[sigma](F2)] = 0.040

  • wR(F2) = 0.115

  • S = 1.02

  • 3323 reflections

  • 182 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.21 e Å-3

  • [Delta][rho]min = -0.24 e Å-3

Data collection: SMART (Bruker, 2001[Bruker (2001). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2001[Bruker (2001). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; 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: SHELXL97.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CI5024 ).

Acknowledgements

The authors thank Professor T. N. Guru Row and Miss Brinda Selvaraj, Solid State and Structural Chemistry Unit, Indian Institute of Science, Bangalore, for their help with the data collection.

References

Alejandro, U., Javier, E., Marcos, R. & Marcela, W. (2008). Molecules, 13, 2385-2393.  [PubMed]
Bogolyubsakaya, L. T. & Perovich, M. (1964). Zh. Obshch. Khim. 34, 3119-3122.
Brady, B., Kenndey, J. & Sullivan, W. (1973). Tetrahedron, 29, 359-362.  [CrossRef] [ChemPort] [ISI]
Bruker (2001). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Deshmukh, M., Kharade, D. & Shirke, S. D. (2004). Monatsh. Chem. 125, 971-976.  [CrossRef]
Devarajegowda, H. C., Sridhar, M. A., Shashidhara Prasad, J., Indira, J., Sooryanarayanarao, B. & Prakash, P. K. (2001). Mol. Cryst. Liq. Cryst. 369, 145-152.  [CrossRef] [ChemPort]
Dhar, D. N. (1981). In The Chemistry of Chalcones and Related Compounds. New York: John Wiley.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  [CrossRef] [details]
Kamal, M., Hassan, A., Eman, A., Mohey, E. & Hanan, A. (2006). Bioorg. Med. Chem. 14, 3672-3680.  [PubMed]
Kant, R., Kamni, Narayana, B., Veena, K. & Yathirajan, H. S. (2009). Acta Cryst. E65, o836.  [CSD] [CrossRef] [details]
Nasef, A. M., El-Naem, S. I. & El-Shabrawy, O. A. (1992). Egypt. J. Pharm. Sci. 34, 463-467.
Rajesh, K., Rajendra, P., Mayur, Y., Shanta, K. & Raju, M. (2006). Indian J. Heterocycl. Chem. 15, 245-253.
Sheldrick, G. M. (2004). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Stanislav, R., Petr, H., Petr, K. & Ivan, K. (2000). Collect. Czech. Chem. Commun. 65, 1093-1108.

Acta Cryst (2010). E66, o466  [ doi:10.1107/S1600536810003004 ]

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.