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Volume 70 
Part 5 
Pages o593-o594  
May 2014  

Received 13 March 2014
Accepted 17 April 2014
Online 26 April 2014

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.002 Å
R = 0.039
wR = 0.128
Data-to-parameter ratio = 17.7
Details
Open access

(E)-3-(4-Hy­droxy-3-meth­oxy­phen­yl)-1-(4-hy­droxy­phen­yl)prop-2-en-1-one

aPG and Research Department of Physics, Queen Mary's College, Chennai-4, Tamilnadu, India, and bPG and Research Department of Chemistry, Presidency College, Chennai-5, Tamil Nadu, India
Correspondence e-mail: guqmc@yahoo.com

In the title compound, C16H14O4, there is an intra­molecular O-H...O hydrogen bond. The benzene rings are inclined to one another by 13.89 (9)°. The prop-2-en-1-one group is twisted slightly, the O=C-Car-Car (ar = aromatic) and C=C-C=O torsion angles being -10.4 (3) and -7.4 (3)°, respectively. In the crystal, mol­ecules are linked by O-H...O hydrogen bonds, forming chains along [100]. These chains are further linked by O-H...O hydrogen bonds, forming corrugated sheets lying parallel to (010). There are C-H...[pi] inter­actions present within the sheets.

Related literature

For the biological activity of chalcones and chalcone derivatives, see: Marais et al. (2005[Marais, J. P. J., Ferreira, D. & Slade, D. (2005). Phytochemistry, 66, 2145-2176.]); Di Carlo et al. (1999[Di Carlo, G., Mascolo, N., Izzo, A. A. & Capasso, F. (1999). Life Sci. 65, 337-353.]); Troeberg et al. (2000[Troeberg, L., Chen, X., Flaherty, T. M., Morty, R. E., Cheng, M., Springer, H. C., McKerrow, J. H., Kenyon, G. L., Lonsdale-Eccles, J. D., Coetzer, T. H. T. & Cohen, F. E. (2000). Mol. Med. 6, 660-669.]); Ni et al. (2004[Ni, L., Meng, C. Q. & Sikorski, J. A. (2004). Exp. Opin. Ther. Pat. 14, 1669-1691.]). For a related structure, see: Jasinski et al. (2011[Jasinski, J. P., Butcher, R. J., Musthafa Khaleel, V., Sarojini, B. K. & Narayana, B. (2011). Acta Cryst. E67, o813.]). For the synthesis, see: Sidharthan et al. (2012[Sidharthan, J., Jonathan, D. R. & Amaladhas, T. P. (2012). Int. J. Chem. Appl. 4, 241-250.]); Chitra et al. (2013[Chitra, M., Jonathan, D. R., Rajan, Y. C. & Duraipandiyan, V. (2013). Int. J. Chem. Appl. 5, 73-81.]). For standard bond lengths, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]).

[Scheme 1]

Experimental

Crystal data
  • C16H14O4

  • Mr = 270.27

  • Orthorhombic, P b c a

  • a = 16.2808 (8) Å

  • b = 10.4348 (5) Å

  • c = 16.2905 (7) Å

  • V = 2767.5 (2) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 0.09 mm-1

  • T = 293 K

  • 0.35 × 0.30 × 0.25 mm

Data collection
  • Bruker Kappa APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2004[Bruker (2004). APEX2, SAINT, XPREP and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.968, Tmax = 0.977

  • 12921 measured reflections

  • 3441 independent reflections

  • 1935 reflections with I > 2[sigma](I)

  • Rint = 0.027

Refinement
  • R[F2 > 2[sigma](F2)] = 0.039

  • wR(F2) = 0.128

  • S = 1.05

  • 3344 reflections

  • 189 parameters

  • 2 restraints

  • H atoms treated by a mixture of independent and constrained refinement

  • [Delta][rho]max = 0.18 e Å-3

  • [Delta][rho]min = -0.20 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C1-C6 benzene ring.

D-H...A D-H H...A D...A D-H...A
O4-H4O...O3 0.86 (2) 2.20 (3) 2.655 (2) 113 (2)
O2-H2O...O1i 0.87 (2) 1.87 (2) 2.7349 (18) 173 (2)
O4-H4O...O1ii 0.86 (2) 2.22 (2) 2.937 (2) 141 (3)
C16-H16A...Cgii 0.96 2.86 3.747 (3) 155
Symmetry codes: (i) [x+{\script{1\over 2}}, y, -z+{\script{1\over 2}}]; (ii) [x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2004[Bruker (2004). APEX2, SAINT, XPREP and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: APEX2 and SAINT (Bruker, 2004[Bruker (2004). APEX2, SAINT, XPREP and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT and XPREP (Bruker, 2004[Bruker (2004). APEX2, SAINT, XPREP and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); program(s) used to solve structure: SIR92 (Altomare et al., 1993[Altomare, A., Cascarano, G., Giacovazzo, C. & Guagliardi, A. (1993). J. Appl. Cryst. 26, 343-350.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).


Supporting information for this paper is available from the IUCr electronic archives (Reference: SU2713 ).


Acknowledgements

The authors thank Professor D. Velmurugan, Centre for Advanced Study in Crystallography and Biophysics, University of Madras, for providing data-collection and computer facilities.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.  [CrossRef]
Altomare, A., Cascarano, G., Giacovazzo, C. & Guagliardi, A. (1993). J. Appl. Cryst. 26, 343-350.  [CrossRef] [Web of Science] [IUCr Journals]
Bruker (2004). APEX2, SAINT, XPREP and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Chitra, M., Jonathan, D. R., Rajan, Y. C. & Duraipandiyan, V. (2013). Int. J. Chem. Appl. 5, 73-81.
Di Carlo, G., Mascolo, N., Izzo, A. A. & Capasso, F. (1999). Life Sci. 65, 337-353.  [Web of Science] [CrossRef] [PubMed] [ChemPort]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Jasinski, J. P., Butcher, R. J., Musthafa Khaleel, V., Sarojini, B. K. & Narayana, B. (2011). Acta Cryst. E67, o813.  [CSD] [CrossRef] [IUCr Journals]
Marais, J. P. J., Ferreira, D. & Slade, D. (2005). Phytochemistry, 66, 2145-2176.  [Web of Science] [CrossRef] [PubMed] [ChemPort]
Ni, L., Meng, C. Q. & Sikorski, J. A. (2004). Exp. Opin. Ther. Pat. 14, 1669-1691.  [CrossRef] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Sidharthan, J., Jonathan, D. R. & Amaladhas, T. P. (2012). Int. J. Chem. Appl. 4, 241-250.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Troeberg, L., Chen, X., Flaherty, T. M., Morty, R. E., Cheng, M., Springer, H. C., McKerrow, J. H., Kenyon, G. L., Lonsdale-Eccles, J. D., Coetzer, T. H. T. & Cohen, F. E. (2000). Mol. Med. 6, 660-669.  [PubMed] [ChemPort]


Acta Cryst (2014). E70, o593-o594   [ doi:10.1107/S1600536814008757 ]

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