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Volume 69 
Part 12 
Page o1809  
December 2013  

Received 6 November 2013
Accepted 18 November 2013
Online 23 November 2013

Key indicators
Single-crystal X-ray study
T = 200 K
Mean [sigma](C-C) = 0.003 Å
R = 0.049
wR = 0.146
Data-to-parameter ratio = 17.6
Details
Open access

(E)-1-(2-Hy­droxy-6-meth­oxy­phen­yl)-3-(2,4,6-tri­meth­oxy­phen­yl)prop-2-en-1-one

aDepartment of Applied Chemistry, Dongduk Women's University, Seoul 136-714, Republic of Korea
Correspondence e-mail: dskoh@dongduk.ac.kr

In the title mol­ecule, C19H20O6, the conformation about the C=C bond of the central enone group is E. The dihedral angle formed by the benzene rings is 11.6 (2)°. The hy­droxy group is involved in an intra­molecular O-H...O hydrogen bond. In the crystal, weak C-H...O hydrogen bonds link the mol­ecules into chains along [010].

Related literature

For the synthesis and biological properties of chalcone deriv­atives, see: Shin et al. (2013[Shin, S. Y., Yoon, H., Hwang, D., Ahn, S., Kim, D.-W., Koh, D., Lee, Y. H. & Lim, Y. (2013). Bioorg. Med. Chem. 21, 7018-7024.]); Yong et al. (2013[Yong, Y., Ahn, S., Hwang, D., Yoon, H., Jo, G., Kim, Y. H., Kim, S. H., Koh, D. & Lim, Y. (2013). Magn. Reson. Chem. 51, 364-370.]); Hsieh et al. (2012[Hsieh, C.-T., Hsieh, T.-J., El-Shazly, M., Chuang, D.-W., Tsai, Y.-H., Yen, C.-T., Wu, S.-F., Wu, Y.-C. & Chang, F.-R. (2012). Bioorg. Med. Chem. Lett. 22, 3912-3915.]); Sashidhara et al. (2011[Sashidhara, K. V., Kumar, M., Modukuri, R. M., Sonkar, R., Bhatia, G., Khanna, A. K., Rai, S. V. & Shukla, R. (2011). Bioorg. Med. Chem. Lett. 21, 4480-4484.]); Sharma et al. (2012[Sharma, V., Singh, G., Kaur, H., Saxena, A. K. & Ishar, M. P. S. (2012). Bioorg. Med. Chem. Lett. 22, 6343-6346.]). For related structures, see: Chantrapromma et al. (2013[Chantrapromma, S., Ruanwas, P., Boonnak, N. & Fun, H.-K. (2013). Acta Cryst. E69, o1004-o1005.]); Li et al. (2013[Li, R., Li, D.-D. & Wu, J.-Y. (2013). Acta Cryst. E69, o1405.]). 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
  • C19H20O6

  • Mr = 344.35

  • Monoclinic, P 21 /c

  • a = 7.2509 (11) Å

  • b = 15.670 (2) Å

  • c = 14.529 (2) Å

  • [beta] = 99.579 (3)°

  • V = 1627.8 (4) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.11 mm-1

  • T = 200 K

  • 0.32 × 0.19 × 0.18 mm

Data collection
  • Bruker SMART CCD diffractometer

  • 11993 measured reflections

  • 4062 independent reflections

  • 1641 reflections with I > 2[sigma](I)

  • Rint = 0.060

Refinement
  • R[F2 > 2[sigma](F2)] = 0.049

  • wR(F2) = 0.146

  • S = 0.83

  • 4062 reflections

  • 231 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.24 e Å-3

  • [Delta][rho]min = -0.30 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O5-H5...O1 0.84 1.73 2.475 (2) 147
C17-H17...O1i 0.95 2.42 3.265 (3) 148
Symmetry code: (i) [-x, y-{\script{1\over 2}}, -z-{\script{1\over 2}}].

Data collection: SMART (Bruker, 2000[Bruker (2000). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2000[Bruker (2000). 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: 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: LH5668 ).


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.
Bruker (2000). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Chantrapromma, S., Ruanwas, P., Boonnak, N. & Fun, H.-K. (2013). Acta Cryst. E69, o1004-o1005.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]
Hsieh, C.-T., Hsieh, T.-J., El-Shazly, M., Chuang, D.-W., Tsai, Y.-H., Yen, C.-T., Wu, S.-F., Wu, Y.-C. & Chang, F.-R. (2012). Bioorg. Med. Chem. Lett. 22, 3912-3915.  [CrossRef] [ChemPort] [PubMed]
Li, R., Li, D.-D. & Wu, J.-Y. (2013). Acta Cryst. E69, o1405.  [CSD] [CrossRef] [IUCr Journals]
Sashidhara, K. V., Kumar, M., Modukuri, R. M., Sonkar, R., Bhatia, G., Khanna, A. K., Rai, S. V. & Shukla, R. (2011). Bioorg. Med. Chem. Lett. 21, 4480-4484.  [CrossRef] [ChemPort] [PubMed]
Sharma, V., Singh, G., Kaur, H., Saxena, A. K. & Ishar, M. P. S. (2012). Bioorg. Med. Chem. Lett. 22, 6343-6346.  [CrossRef] [ChemPort] [PubMed]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Shin, S. Y., Yoon, H., Hwang, D., Ahn, S., Kim, D.-W., Koh, D., Lee, Y. H. & Lim, Y. (2013). Bioorg. Med. Chem. 21, 7018-7024.  [CrossRef] [ChemPort] [PubMed]
Yong, Y., Ahn, S., Hwang, D., Yoon, H., Jo, G., Kim, Y. H., Kim, S. H., Koh, D. & Lim, Y. (2013). Magn. Reson. Chem. 51, 364-370.  [Web of Science] [CrossRef] [ChemPort] [PubMed]


Acta Cryst (2013). E69, o1809  [ doi:10.1107/S1600536813031498 ]

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