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Volume 69 
Part 5 
Page o666  
May 2013  

Received 22 February 2013
Accepted 2 April 2013
Online 5 April 2013

Key indicators
Single-crystal X-ray study
T = 200 K
Mean [sigma](C-C) = 0.003 Å
R = 0.044
wR = 0.115
Data-to-parameter ratio = 13.0
Details
Open access

(E)-1-(3,5-Dimethoxyphenyl)-3-(3-methoxyphenyl)prop-2-en-1-one

aDepartment of Applied Chemistry, Dongduk Women's University, Seoul 136-714, Republic of Korea,bJeonju Center, Korea Basic Science Center (KBSI), Jeonju 561-765, Republic of Korea, and cDivision of Bioscience and Biotechnology, BMIC, Konkuk University, Seoul 143-701, Republic of Korea
Correspondence e-mail: dskoh@dongduk.ac.kr

In the title molecule, C18H18O4, the C=C bond of the central enone group adopts a trans conformation. The relative conformation of the C=O and C=C bonds is s-cisoid. The dihedral angle between the planes of the benzene rings is 29.49 (12)°. 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: Shenvi et al. (2013[Shenvi, S., Kumar, K., Hatti, K. S., Rijesh, K., Diwakar, L. & Reddy, G. C. (2013). Eur. J. Med. Chem. 62, 435-442.]); Hsieh et al. (2012[Hsieh, C.-T., Hsieh, T.-J., El-Shazly, M., Chuang, D.-W., Tsai, Y.-H., Yen a, C.-T., Wua, S.-F., Wua, Y.-C. & Chang, F.-R. (2012). Bioorg. Med. Chem. Lett. 22, 3912-3915.]); Hwang et al. (2011[Hwang, D., Hyun, J., Jo, G., Koh, D. & Lim, Y. (2011). Magn. Reson. Chem. 49, 41-45.]); Jo et al. (2012[Jo, G., Sung, S. H., Lee, Y., Kim, B.-G., Yoon, J. W., Lee, H. K., Ji, S. Y., Koh, D., Ahn, J. H. & Lim, Y. (2012). Bull. Korean Chem. Soc. 33, 3841-3844.]); 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.]); 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.]). For related structures, see: Carvalho-Jr et al. (2011[Carvalho-Jr, P. S., Sallum, L. O., Cidade, A. F., Aquino, G. L. B. & Napolitano, H. B. (2011). Acta Cryst. E67, o2126.]); Wu et al. (2012[Wu, J., Qiu, J., Wu, X., Yang, S. & Liu, Y. (2012). Acta Cryst. E68, o154.]).

[Scheme 1]

Experimental

Crystal data
  • C18H18O4

  • Mr = 298.32

  • Triclinic, [P \overline 1]

  • a = 8.2402 (12) Å

  • b = 9.1449 (14) Å

  • c = 10.8876 (16) Å

  • [alpha] = 95.395 (3)°

  • [beta] = 107.667 (3)°

  • [gamma] = 102.837 (3)°

  • V = 750.61 (19) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.09 mm-1

  • T = 200 K

  • 0.33 × 0.26 × 0.12 mm

Data collection
  • Bruker SMART CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2000[Bruker (2000). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.970, Tmax = 0.989

  • 4383 measured reflections

  • 2619 independent reflections

  • 1531 reflections with I > 2[sigma](I)

  • Rint = 0.028

Refinement
  • R[F2 > 2[sigma](F2)] = 0.044

  • wR(F2) = 0.115

  • S = 0.98

  • 2619 reflections

  • 202 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.20 e Å-3

  • [Delta][rho]min = -0.26 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C7-H7...O4i 0.95 2.55 3.405 (3) 151
C9-H9C...O1ii 0.98 2.50 3.388 (3) 150
Symmetry codes: (i) -x, -y+1, -z+2; (ii) x, y+1, z.

Data collection: SMART (Bruker, 2000[Bruker (2000). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2000[Bruker (2000). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: SHELXTL.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LH5590 ).


References

Bruker (2000). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Carvalho-Jr, P. S., Sallum, L. O., Cidade, A. F., Aquino, G. L. B. & Napolitano, H. B. (2011). Acta Cryst. E67, o2126.  [CrossRef] [details]
Hsieh, C.-T., Hsieh, T.-J., El-Shazly, M., Chuang, D.-W., Tsai, Y.-H., Yen a, C.-T., Wua, S.-F., Wua, Y.-C. & Chang, F.-R. (2012). Bioorg. Med. Chem. Lett. 22, 3912-3915.  [CrossRef] [ChemPort] [PubMed]
Hwang, D., Hyun, J., Jo, G., Koh, D. & Lim, Y. (2011). Magn. Reson. Chem. 49, 41-45.  [ISI] [CrossRef] [ChemPort] [PubMed]
Jo, G., Sung, S. H., Lee, Y., Kim, B.-G., Yoon, J. W., Lee, H. K., Ji, S. Y., Koh, D., Ahn, J. H. & Lim, Y. (2012). Bull. Korean Chem. Soc. 33, 3841-3844.  [ChemPort]
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] [details]
Shenvi, S., Kumar, K., Hatti, K. S., Rijesh, K., Diwakar, L. & Reddy, G. C. (2013). Eur. J. Med. Chem. 62, 435-442.  [CrossRef] [ChemPort] [PubMed]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [ChemPort] [details]
Wu, J., Qiu, J., Wu, X., Yang, S. & Liu, Y. (2012). Acta Cryst. E68, o154.  [CSD] [CrossRef] [details]


Acta Cryst (2013). E69, o666  [ doi:10.1107/S1600536813008982 ]

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