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Volume 69 
Part 5 
Page o629  
May 2013  

Received 14 March 2013
Accepted 22 March 2013
Online 5 April 2013

Key indicators
Single-crystal X-ray study
T = 298 K
Mean [sigma](C-C) = 0.004 Å
R = 0.048
wR = 0.168
Data-to-parameter ratio = 13.0
Details
Open access

2,4-Dimethoxy-6-[(E)-2-(4-methoxyphenyl)ethenyl]benzaldehyde

aSchool of Medical Engineering, Hefei University of Technology, Hefei 230009, People's Repulic of China
Correspondence e-mail: ruanbf@hfut.edu.cn

There are two conformationally similar molecules in the asymmetric unit of he title compound, C18H18O4, in which the dihedral angles between the benzene rings are 23.54 (12) and 31.11 (12)°. In the crystal, C-H...[pi] interactions (minimum H...ring centroid distance = 2.66 Å) link the molecules into a layered structure extending down a.

Related literature

The title compound is a derivative of the natural product resveratrol (trans-3,4,5-trihydroxystilbene). For background to resveratrol, see: Jang et al. (1997[Jang, M., Cai, L., Udeani, G. O., Slowing, K. V., Thomas, C. F., Beecher, C. W. W., Fong, H. H. S., Farnworth, R. N., Kinghorn, A. D., Metha, R. G., Moon, R. C. & Pezzuto, J. M. (1997). Science, 275, 218-220.]); Orsini et al. (1997[Orsini, F., Pelizzoni, F., Verotta, L. & Aburjai, T. (1997). J. Nat. Prod. 60, 1082-1087.]); Pettit et al. (2002[Pettit, G. R., Grealish, M. P., Jung, M. K., Hamel, E., Pettit, R. K., Chapuis, J. C. & Schmidt, J. M. (2002). J. Med. Chem. 45, 2534-2542.]). For standard bond lengths and angles, see: Boumendjel et al. (2008[Boumendjel, A., Boccard, J., Carrupt, P. A., Nicolle, E., Blanc, M., Geze, A., Choisnard, L., Wouessidjewe, D., Matera, E. L. & Dumontet, C. (2008). J. Med. Chem. 51, 2307-2310.]). For the synthesis of the title compound, see: Huang et al. (2007[Huang, X. F., Ruan, B. F., Wang, X. T., Xu, C., Ge, H. M., Zhu, H. L. & Tan, R. X. (2007). Eur. J. Med. Chem. 42, 263-267.]).

[Scheme 1]

Experimental

Crystal data
  • C18H18O4

  • Mr = 298.32

  • Triclinic, [P \overline 1]

  • a = 9.292 (5) Å

  • b = 9.448 (5) Å

  • c = 17.547 (5) Å

  • [alpha] = 84.097 (5)°

  • [beta] = 84.040 (5)°

  • [gamma] = 83.315 (5)°

  • V = 1515.3 (12) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.09 mm-1

  • T = 298 K

  • 0.30 × 0.20 × 0.20 mm

Data collection
  • Bruker SMART CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2000[Bruker (2000). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.973, Tmax = 0.982

  • 10535 measured reflections

  • 5272 independent reflections

  • 3060 reflections with I > 2[sigma](I)

  • Rint = 0.039

Refinement
  • R[F2 > 2[sigma](F2)] = 0.048

  • wR(F2) = 0.168

  • S = 0.79

  • 5272 reflections

  • 404 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.15 e Å-3

  • [Delta][rho]min = -0.18 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg2 and Cg4 are the centroids of the C12-C17 and C30-C35 rings, respectively.

D-H...A D-H H...A D...A D-H...A
C14-H14...Cg4i 0.93 2.88 3.597 (3) 135
C17-H14...Cg4ii 0.93 2.76 3.471 (3) 134
C32-H14...Cg2 0.93 2.82 3.530 (3) 135
C15-H14...Cg2iii 0.93 2.66 3.371 (3) 134
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) -x, -y+1, -z+1; (iii) x+1, y, 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: 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: ZS2252 ).


Acknowledgements

This work was supported by Anhui Provincial Natural Science Foundation (grant No. 1308085MB18).<

References

Boumendjel, A., Boccard, J., Carrupt, P. A., Nicolle, E., Blanc, M., Geze, A., Choisnard, L., Wouessidjewe, D., Matera, E. L. & Dumontet, C. (2008). J. Med. Chem. 51, 2307-2310.  [ISI] [CrossRef] [PubMed] [ChemPort]
Bruker (2000). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Huang, X. F., Ruan, B. F., Wang, X. T., Xu, C., Ge, H. M., Zhu, H. L. & Tan, R. X. (2007). Eur. J. Med. Chem. 42, 263-267.  [ISI] [CrossRef] [PubMed] [ChemPort]
Jang, M., Cai, L., Udeani, G. O., Slowing, K. V., Thomas, C. F., Beecher, C. W. W., Fong, H. H. S., Farnworth, R. N., Kinghorn, A. D., Metha, R. G., Moon, R. C. & Pezzuto, J. M. (1997). Science, 275, 218-220.  [CrossRef] [ChemPort] [PubMed] [ISI]
Orsini, F., Pelizzoni, F., Verotta, L. & Aburjai, T. (1997). J. Nat. Prod. 60, 1082-1087.  [CrossRef] [ChemPort] [PubMed] [ISI]
Pettit, G. R., Grealish, M. P., Jung, M. K., Hamel, E., Pettit, R. K., Chapuis, J. C. & Schmidt, J. M. (2002). J. Med. Chem. 45, 2534-2542.  [ISI] [CrossRef] [PubMed] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]


Acta Cryst (2013). E69, o629  [ doi:10.1107/S1600536813007964 ]

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