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Volume 68 
Part 1 
Page o154  
January 2012  

Received 4 December 2011
Accepted 9 December 2011
Online 17 December 2011

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.002 Å
R = 0.046
wR = 0.126
Data-to-parameter ratio = 14.6
Details
Open access

(E)-3-(2,4-Dimethoxyphenyl)-1-(3,4,5-trimethoxyphenyl)prop-2-en-1-one

aInstitute of Biotechnology, Nanjing University of Science and Technology, Nanjing, Jiangsu Province 210094, People's Republic of China,bSchool of Pharmacy, Wenzhou Medical College, Wenzhou, Zhejiang Province 325035, People's Republic of China,cLife Science College, Wenzhou Medical College, Wenzhou, Zhejiang Province 325035, People's Republic of China, and dSchool of Pharmacy, Hainan Medical College, Haikou, Hainan Province 571101, People's Republic of China
Correspondence e-mail: wjzwzmc@126.com

In the title chalcone derivative, C20H22O6, the dihedral angle between the mean planes of the benzene rings is 15.77 (6)°. The H atoms of the central C=C double bond are in a trans configuration. There are a number of C-H...O interactions and a C-H...[pi] interaction present in the crystal structure.

Related literature

For related structures, see: Wu et al. (2010[Wu, J., Wang, C., Cai, Y., Yang, S., Zheng, X., Qiu, P., Peng, J., Wu, X., Liang, G. & Li, X. (2010). Chin. J. Org. Chem. 30, 884-889.], 2011[Wu, J., Li, J., Cai, Y., Pan, Y., Ye, F., Zhang, Y., Zhao, Y., Yang, S., Li, X. & Liang, G. (2011). J. Med. Chem. 54, 8110-8123.]); Huang et al. (2010[Huang, T., Zhang, D., Yang, Q., Wei, X. & Wu, J. (2010). Acta Cryst. E66, o2518.]); Peng et al. (2010[Peng, J., Xu, H., Li, Z., Zhang, Y. & Wu, J. (2010). Acta Cryst. E66, o1156-o1157.]). For applications of chalcones, see: Wu et al. (2010[Wu, J., Wang, C., Cai, Y., Yang, S., Zheng, X., Qiu, P., Peng, J., Wu, X., Liang, G. & Li, X. (2010). Chin. J. Org. Chem. 30, 884-889.], 2011[Wu, J., Li, J., Cai, Y., Pan, Y., Ye, F., Zhang, Y., Zhao, Y., Yang, S., Li, X. & Liang, G. (2011). J. Med. Chem. 54, 8110-8123.]); Nielsen et al. (2005[Nielsen, S. F., Larsen, M., Boesen, T., Schønning, K. & Kromann, H. (2005). J. Med. Chem. 48, 2667-2677.]). For the hydrogen-bond analysis, see: Spek (2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

[Scheme 1]

Experimental

Crystal data
  • C20H22O6

  • Mr = 358.38

  • Monoclinic, P 21 /c

  • a = 8.3111 (11) Å

  • b = 13.8493 (17) Å

  • c = 15.887 (2) Å

  • [beta] = 101.588 (2)°

  • V = 1791.4 (4) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.10 mm-1

  • T = 293 K

  • 0.40 × 0.37 × 0.31 mm

Data collection
  • Bruker SMART CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2001[Bruker (2001). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.651, Tmax = 1.000

  • 9663 measured reflections

  • 3512 independent reflections

  • 2452 reflections with I > 2[sigma](I)

  • Rint = 0.045

Refinement
  • R[F2 > 2[sigma](F2)] = 0.046

  • wR(F2) = 0.126

  • S = 0.97

  • 3512 reflections

  • 241 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.20 e Å-3

  • [Delta][rho]min = -0.19 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C4-C9 ring.

D-H...A D-H H...A D...A D-H...A
C8-H8...O6i 0.93 2.65 3.562 (2) 166
C18-H18B...O3ii 0.96 2.64 3.404 (2) 136
C16-H16B...O2iii 0.96 2.68 3.389 (2) 132
C16-H16C...O1iii 0.96 2.66 3.608 (3) 169
C19-H19C...Cg1iv 0.96 2.79 3.530 (2) 134
Symmetry codes: (i) [x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]; (ii) x, y, z-1; (iii) [x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]; (iv) -x, -y+1, -z.

Data collection: SMART (Bruker, 2001[Bruker (2001). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2001[Bruker (2001). 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: ZQ2146 ).


Acknowledgements

The authors are grateful to the associate researcher Sun Jie from Shanghai Institute of Organic Chemistry, Chinese academy of Sciences for testing and crystal analysis. This study was partially supported by the Zhejiang Natural Science Funds (Y2101108) and the University Students in Zhejiang Science and Technology Innovation Projects (2011R413025).

References

Bruker (2001). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Huang, T., Zhang, D., Yang, Q., Wei, X. & Wu, J. (2010). Acta Cryst. E66, o2518.  [CSD] [CrossRef] [details]
Nielsen, S. F., Larsen, M., Boesen, T., Schønning, K. & Kromann, H. (2005). J. Med. Chem. 48, 2667-2677.  [ISI] [CrossRef] [PubMed] [ChemPort]
Peng, J., Xu, H., Li, Z., Zhang, Y. & Wu, J. (2010). Acta Cryst. E66, o1156-o1157.  [CSD] [CrossRef] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]
Wu, J., Li, J., Cai, Y., Pan, Y., Ye, F., Zhang, Y., Zhao, Y., Yang, S., Li, X. & Liang, G. (2011). J. Med. Chem. 54, 8110-8123.  [CrossRef] [ChemPort] [PubMed]
Wu, J., Wang, C., Cai, Y., Yang, S., Zheng, X., Qiu, P., Peng, J., Wu, X., Liang, G. & Li, X. (2010). Chin. J. Org. Chem. 30, 884-889.


Acta Cryst (2012). E68, o154  [ doi:10.1107/S1600536811053001 ]

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