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Volume 68 
Part 12 
Page o3386  
December 2012  

Received 4 November 2012
Accepted 14 November 2012
Online 17 November 2012

Key indicators
Single-crystal X-ray study
T = 200 K
Mean [sigma](C-C) = 0.003 Å
R = 0.041
wR = 0.101
Data-to-parameter ratio = 19.3
Details
Open access

(2E)-3-[4-(Benzyloxy)phenyl]-1-(2,6-dichloro-3-fluorophenyl)prop-2-en-1-one

aUniversity of Mysore, Department of Studies in Chemistry, Manasagangotri, Mysore 570 006, India, and bNelson Mandela Metropolitan University, Summerstrand Campus, Department of Chemistry, University Way, Summerstrand, PO Box 77000, Port Elizabeth, 6031, South Africa
Correspondence e-mail: richard.betz@webmail.co.za

In the title compound, C22H15Cl2FO2, a chalcone derivative featuring a threefold-halogenated aromatic substituent, the conformation about the C=C bond is E. In the crystal C-H...F and C-H...Cl contacts connect the molecules into undulating sheets parallel to (101). In addition, C-H...[pi] interactions are also present.

Related literature

For background to possible applications of chalcones in pharmacy and industry, see: Lin et al. (2002[Lin, Y. M., Zhou, Y., Flavin, M. T., Zhou, L. M., Nie, W. & Chen, F. C. (2002). Bioorg. Med. Chem. 10, 2795-2802.]); Modzelewska et al. (2006[Modzelewska, A., Pettit, C., Achanta, G., Davidson, N. E., Huang, P. & Khan, S. R. (2006). Bioorg. Med. Chem. 14, 3491-3495.]); Svetaz et al. (2004[Svetaz, L., Tapia, A., Lopez, S., Furlan, R. L. E., Petenatti, E., Pioli, R., Schmeda-Hirschmann, G. & Zacchino, S. A. (2004). J. Agric. Food Chem. 52, 3297-3300.]); Sarojini et al. (2006[Sarojini, B. K., Narayana, B., Ashalatha, B. V., Indira, J. & Lobo, K. G. (2006). J. Cryst. Growth, 295, 54-59.]). For related structures, see: Yathirajan et al. (2006[Yathirajan, H. S., Sarojini, B. K., Narayana, B., Bindya, S. & Bolte, M. (2006). Acta Cryst. E62, o3631-o3632.]); Betz et al. (2012[Betz, R., Gerber, T., Hosten, E., Praveen, A. S., Yathirajan, H. S. & Narayana, B. (2012). Acta Cryst. E68, o512.]). For graph-set analysis of hydrogen bonds, see: Etter et al. (1990[Etter, M. C., MacDonald, J. C. & Bernstein, J. (1990). Acta Cryst. B46, 256-262.]); Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]).

[Scheme 1]

Experimental

Crystal data
  • C22H15Cl2FO2

  • Mr = 401.24

  • Monoclinic, P 21 /c

  • a = 9.1977 (2) Å

  • b = 21.6887 (4) Å

  • c = 11.6072 (2) Å

  • [beta] = 124.629 (1)°

  • V = 1905.29 (6) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.36 mm-1

  • T = 200 K

  • 0.40 × 0.17 × 0.14 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2008[Bruker (2008). SADABS. Bruker Inc., Madison, Wisconsin, USA.]) Tmin = 0.681, Tmax = 0.746

  • 17237 measured reflections

  • 4712 independent reflections

  • 3729 reflections with I > 2[sigma](I)

  • Rint = 0.027

Refinement
  • R[F2 > 2[sigma](F2)] = 0.041

  • wR(F2) = 0.101

  • S = 1.02

  • 4712 reflections

  • 244 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.40 e Å-3

  • [Delta][rho]min = -0.27 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C21-C26 ring.

D-H...A D-H H...A D...A D-H...A
C23-H23...F1i 0.95 2.55 3.375 (2) 145
C34-H34...Cl1ii 0.95 2.80 3.5462 (18) 136
C14-H14...Cgiii 0.95 2.51 3.297 (2) 140
Symmetry codes: (i) [-x+2, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]; (ii) [-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]; (iii) [x+1, -y-{\script{1\over 2}}, z-{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2010[Bruker (2010). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2010[Bruker (2010). APEX2 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, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and Mercury (Macrae et al., 2008[Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.]); software used to prepare material for publication: SHELXL97 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: NC2298 ).


Acknowledgements

ASP thanks the UOM for research facilities.

References

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.  [CrossRef] [ChemPort] [ISI]
Betz, R., Gerber, T., Hosten, E., Praveen, A. S., Yathirajan, H. S. & Narayana, B. (2012). Acta Cryst. E68, o512.  [CSD] [CrossRef] [details]
Bruker (2008). SADABS. Bruker Inc., Madison, Wisconsin, USA.
Bruker (2010). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Etter, M. C., MacDonald, J. C. & Bernstein, J. (1990). Acta Cryst. B46, 256-262.  [CrossRef] [ISI] [details]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Lin, Y. M., Zhou, Y., Flavin, M. T., Zhou, L. M., Nie, W. & Chen, F. C. (2002). Bioorg. Med. Chem. 10, 2795-2802.  [CrossRef] [PubMed] [ChemPort]
Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.  [ISI] [CrossRef] [ChemPort] [details]
Modzelewska, A., Pettit, C., Achanta, G., Davidson, N. E., Huang, P. & Khan, S. R. (2006). Bioorg. Med. Chem. 14, 3491-3495.  [CrossRef] [PubMed] [ChemPort]
Sarojini, B. K., Narayana, B., Ashalatha, B. V., Indira, J. & Lobo, K. G. (2006). J. Cryst. Growth, 295, 54-59.  [ISI] [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]
Svetaz, L., Tapia, A., Lopez, S., Furlan, R. L. E., Petenatti, E., Pioli, R., Schmeda-Hirschmann, G. & Zacchino, S. A. (2004). J. Agric. Food Chem. 52, 3297-3300.  [ISI] [CrossRef] [PubMed] [ChemPort]
Yathirajan, H. S., Sarojini, B. K., Narayana, B., Bindya, S. & Bolte, M. (2006). Acta Cryst. E62, o3631-o3632.  [CSD] [CrossRef] [details]


Acta Cryst (2012). E68, o3386  [ doi:10.1107/S1600536812046855 ]

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