[Journal logo]

Volume 69 
Part 6 
Page o960  
June 2013  

Received 9 April 2013
Accepted 18 May 2013
Online 25 May 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.002 Å
Disorder in main residue
R = 0.043
wR = 0.129
Data-to-parameter ratio = 14.3
Details
Open access

(E)-3-(3,4-Difluorophenyl)-1-(3,4-dimethoxyphenyl)prop-2-en-1-one

aSchool of Pharmaceutical Sciences, Wenzhou Medical College, Wenzhou 325035, People's Republic of China
Correspondence e-mail: lzgcnu@163.com

In the title compound, C17H14F2O3, the dihedral angle between the benzene rings is 20.56 (8)° and the H atoms at the central propenone group are trans configured. One of the F atoms is disordered over two positions (occupancy ratio 0.57:0.43) and was refined using a split model. In the crystal, the molecules are linked into centrosymmetrical dimers and are further connected into a three-dimensional network via weak C-H...O interactions.

Related literature

For related structures, see: Peng et al.(2010[Peng, J., Xu, H., Li, Z., Zhang, Y. & Wu, J. (2010). Acta Cryst. E66, o1156-o1157.]); Wu et al. (2010[Wu, X., Cai, X., Zheng, X., Zhang, Z. & Ye, X. (2010). Acta Cryst. E66, o3015.], 2011[Wu, J. Z., Li, J. L., Cai, Y. P., Pan, Y., Ye, F. Q., Zhang, Y. L., Zhao, Y. J., Yang, S. L., Li, X. K. & Liang, G. (2011). J. Med. Chem. 54, 8110-8123.], 2012b[Wu, J. Z., Jiang, X., Zhao, C. G., Li, X. K. & Yang, S. L. (2012b). Z. Kristallogr. New Cryst. Struct. 227, 215-216.]). For background to and applications of chalcones, see: Boumendjel et al. (2008[Boumendjel, A., Boccard, J., Carrupt, P. A., Nicolle, E., Blanc, M., Geze, A., Choisnard, L., Wouessidjewe, D., Matera, E. L. & Dumontet, C. (2008). J. Med. Chem. 51, 2307-2310.]); Kumar et al. (2011[Kumar, V., Kumar, S., Hassan, M., Wu, H., Thimmulappa, R. K., Kumar, A., Sharma, S. K., Parmar, V. S., Biswal, S. & Malhotra, S. V. (2011). J. Med. Chem. 54, 4147-4159.]); Wu et al. (2011[Wu, J. Z., Li, J. L., Cai, Y. P., Pan, Y., Ye, F. Q., Zhang, Y. L., Zhao, Y. J., Yang, S. L., Li, X. K. & Liang, G. (2011). J. Med. Chem. 54, 8110-8123.], 2012a[Wu, J. Z., Wang, C., Cai, Y. P., Peng, J., Liang, D. L., Zhao, Y. J., Yang, S. L., Li, X. K., Wu, X. P. & Liang, G. (2012a). Med. Chem. Res. 21, 444-452.]); Zhang et al. (2011[Zhang, H. J., Qian, Y., Zhu, D. D., Yang, X. G. & Zhu, H. L. (2011). Eur. J. Med. Chem. 46, 4702-4708.]).

[Scheme 1]

Experimental

Crystal data
  • C17H14F2O3

  • Mr = 304.28

  • Monoclinic, P 21 /n

  • a = 8.7444 (9) Å

  • b = 8.4832 (9) Å

  • c = 19.829 (2) Å

  • [beta] = 94.053 (2)°

  • V = 1467.2 (3) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.11 mm-1

  • T = 293 K

  • 0.21 × 0.15 × 0.11 mm

Data collection
  • Bruker SMART CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2002[Bruker (2002). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.977, Tmax = 0.988

  • 8592 measured reflections

  • 2876 independent reflections

  • 2121 reflections with I > 2[sigma](I)

  • Rint = 0.028

Refinement
  • R[F2 > 2[sigma](F2)] = 0.043

  • wR(F2) = 0.129

  • S = 1.04

  • 2876 reflections

  • 201 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.19 e Å-3

  • [Delta][rho]min = -0.15 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C1-H1...O1i 0.93 2.44 3.321 (2) 159
C5-H5...O2ii 0.93 2.60 3.2769 (15) 130
C5-H5...O3ii 0.93 2.49 3.3950 (15) 164
Symmetry codes: (i) -x+1, -y+1, -z; (ii) [-x+{\script{3\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}].

Data collection: SMART (Bruker, 2002[Bruker (2002). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2002[Bruker (2002). SMART, SAINT and SADABS. 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: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: NC2310 ).


Acknowledgements

This work was supported by Xinmiao Talent Project of Zhejiang Province (ZHP). The X-ray crystallographic facility at the Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, is gratefully acknowledged.

References

Boumendjel, A., Boccard, J., Carrupt, P. A., Nicolle, E., Blanc, M., Geze, A., Choisnard, L., Wouessidjewe, D., Matera, E. L. & Dumontet, C. (2008). J. Med. Chem. 51, 2307-2310.  [ISI] [CrossRef] [PubMed] [ChemPort]
Bruker (2002). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Kumar, V., Kumar, S., Hassan, M., Wu, H., Thimmulappa, R. K., Kumar, A., Sharma, S. K., Parmar, V. S., Biswal, S. & Malhotra, S. V. (2011). J. Med. Chem. 54, 4147-4159.  [ISI] [CrossRef] [ChemPort] [PubMed]
Peng, J., Xu, H., Li, Z., Zhang, Y. & Wu, J. (2010). Acta Cryst. E66, o1156-o1157.  [CSD] [CrossRef] [ChemPort] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Wu, X., Cai, X., Zheng, X., Zhang, Z. & Ye, X. (2010). Acta Cryst. E66, o3015.  [CSD] [CrossRef] [details]
Wu, J. Z., Jiang, X., Zhao, C. G., Li, X. K. & Yang, S. L. (2012b). Z. Kristallogr. New Cryst. Struct. 227, 215-216.  [ChemPort]
Wu, J. Z., Li, J. L., Cai, Y. P., Pan, Y., Ye, F. Q., Zhang, Y. L., Zhao, Y. J., Yang, S. L., Li, X. K. & Liang, G. (2011). J. Med. Chem. 54, 8110-8123.  [ISI] [CrossRef] [ChemPort] [PubMed]
Wu, J. Z., Wang, C., Cai, Y. P., Peng, J., Liang, D. L., Zhao, Y. J., Yang, S. L., Li, X. K., Wu, X. P. & Liang, G. (2012a). Med. Chem. Res. 21, 444-452.  [ISI] [CSD] [CrossRef] [ChemPort]
Zhang, H. J., Qian, Y., Zhu, D. D., Yang, X. G. & Zhu, H. L. (2011). Eur. J. Med. Chem. 46, 4702-4708.  [ISI] [CSD] [CrossRef] [ChemPort] [PubMed]


Acta Cryst (2013). E69, o960  [ doi:10.1107/S1600536813013767 ]

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.