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Volume 70 
Part 1 
Page o88  
January 2014  

Received 20 November 2013
Accepted 11 December 2013
Online 24 December 2013

Key indicators
Single-crystal X-ray study
T = 173 K
Mean [sigma](C-C) = 0.003 Å
R = 0.053
wR = 0.147
Data-to-parameter ratio = 12.0
Details
Open access

(2Z,4E)-1-(5-Fluoro-2-hy­droxy­phen­yl)-5-(4-fluoro­phen­yl)-3-hy­droxy­penta-2,4-dien-1-one

aThe Key Laboratory for Chemical Biology of Fujian Province, Xiamen University, Xiamen 361005, People's Republic of China,bSchool of Pharmaceutical Sciences, Xiamen University, Sounth Xiang-An Road, Xiamen 361100, People's Republic of China, and cState Ocean Adm, Inst Oceanog 3, Xiamen 361005, People's Republic of China
Correspondence e-mail: fangmj@xmu.edu.cn

In the title mol­ecule, C17H12F2O3, the dihedral angle between the benzene rings is 8.6 (2)°. In the crystal, two pairs of O-H...O hydrogen bonds connect the mol­ecules into inversion dimers. In addition, weak C-H...F hydrogen bonds link the dimers into a two-dimensional network parallel to (10-4). The carbonyl O atom is an acceptor for two weak intra­molecular hydrogen bonds.

Related literature

For the biological activities of chalcones, see: Meng et al. (2007[Meng, C. Q., Ni, L. M., Worsencroft, K. J., Ye, Z., Weingarten, D. M., Simpson, J. E., Skudlarek, J. W., Marino, E. M., Suen, K. L., Kunsch, C., Souder, A., Howard, R. B., Sundell, C. L., Wasserman, M. A. & Sikorski, J. A. (2007). J. Med. Chem. 50, 1304-1315.]); Schobert et al. (2009[Schobert, R., Biersack, B., Dietrich, A., Knauer, S., Zoldakova, M., Fruehauf, A. & Mueller, T. (2009). J. Med. Chem. 52, 241-246.]). For the synthesis, see: Baker (1933[Baker, W. J. (1933). J. Chem. Soc. pp. 1381-1389.]); Mahal & Venkataraman (1934[Mahal, H. S. & Venkataraman, K. (1934). J. Chem. Soc. pp. 1767-1769.]). For a related structure, see: Fun et al. (2012[Fun, H.-K., Farhadikoutenaei, A., Narayana, B., Nayak, P. S. & Sarojini, B. K. (2012). Acta Cryst. E68, o2658.]).

[Scheme 1]

Experimental

Crystal data
  • C17H12F2O3

  • Mr = 302.27

  • Monoclinic, P 21 /c

  • a = 6.8275 (18) Å

  • b = 14.004 (4) Å

  • c = 14.267 (4) Å

  • [beta] = 91.293 (5)°

  • V = 1363.8 (7) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.12 mm-1

  • T = 173 K

  • 0.32 × 0.23 × 0.18 mm

Data collection
  • Bruker APEX CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2001[Bruker (2001). SAINT, SMART and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.963, Tmax = 0.979

  • 6787 measured reflections

  • 2392 independent reflections

  • 2040 reflections with I > 2[sigma](I)

  • Rint = 0.028

Refinement
  • R[F2 > 2[sigma](F2)] = 0.053

  • wR(F2) = 0.147

  • S = 1.08

  • 2392 reflections

  • 199 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.21 e Å-3

  • [Delta][rho]min = -0.29 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O1-H1A...O2 0.82 1.84 2.558 (2) 145
O1-H1A...O3i 0.82 2.55 3.145 (2) 130
O3-H3A...O2 0.82 1.81 2.532 (2) 146
O3-H3A...O2i 0.82 2.38 2.856 (2) 118
C10-H10A...F2ii 0.93 2.51 3.326 (3) 147
Symmetry codes: (i) -x-1, -y+2, -z+1; (ii) [-x-3, y+{\script{1\over 2}}, -z+{\script{1\over 2}}].

Data collection: SMART (Bruker, 2001[Bruker (2001). SAINT, SMART and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2001[Bruker (2001). SAINT, SMART 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.]) and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: SHELXL97.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LH5672 ).


Acknowledgements

This work was supported financially by the National Science Foundation of China (grants No. 81072549 and 81302652) and the Natural Science Foundation of Fujian Province of China (grant No. 2011 J05101)

References

Baker, W. J. (1933). J. Chem. Soc. pp. 1381-1389.  [CrossRef]
Bruker (2001). SAINT, SMART and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Fun, H.-K., Farhadikoutenaei, A., Narayana, B., Nayak, P. S. & Sarojini, B. K. (2012). Acta Cryst. E68, o2658.  [CrossRef] [IUCr Journals]
Mahal, H. S. & Venkataraman, K. (1934). J. Chem. Soc. pp. 1767-1769.  [CrossRef]
Meng, C. Q., Ni, L. M., Worsencroft, K. J., Ye, Z., Weingarten, D. M., Simpson, J. E., Skudlarek, J. W., Marino, E. M., Suen, K. L., Kunsch, C., Souder, A., Howard, R. B., Sundell, C. L., Wasserman, M. A. & Sikorski, J. A. (2007). J. Med. Chem. 50, 1304-1315.  [CrossRef] [PubMed] [ChemPort]
Schobert, R., Biersack, B., Dietrich, A., Knauer, S., Zoldakova, M., Fruehauf, A. & Mueller, T. (2009). J. Med. Chem. 52, 241-246.  [CrossRef] [PubMed] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]


Acta Cryst (2014). E70, o88  [ doi:10.1107/S1600536813033564 ]

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