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Volume 66 
Part 10 
Page o2678  
October 2010  

Received 6 July 2010
Accepted 16 September 2010
Online 30 September 2010

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Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.002 Å
R = 0.045
wR = 0.110
Data-to-parameter ratio = 18.0
Details
Open access

(1E,3E)-1,4-Bis(4-methoxyphenyl)buta-1,3-diene

Gopinathan Narayan,a+ Nigam P. Rathb and Suresh Dasa*

aPhotosciences and Photonics Section, Chemical Sciences and Technology Division, National Institute for Interdisciplinary Science and Technology, CSIR, Trivandrum, Kerala 695 019, India, and bDepartment of Chemistry and Biochemistry and Center for Nanoscience, University of Missouri-St. Louis, One University Boulevard, St. Louis, MO 63121-4400, USA
Correspondence e-mail: sureshdas@niist.res.in

The title compound, C18H18O2, which exhibits blue emission in the solid state, is an intermediate in the preparation of liquid crystals and polymers. The molecule is located on an inversion centre. In the crystal, molecules are arranged in a herringbone motif.

Related literature

For related structures, see: George et al. (1998[George, M., Das, S., Ashokan, C. V., Rath, N. P. & George, M. V. (1998). Acta Cryst. C54, 1033-1036.]); Vishnumurthy et al. (2002[Vishnumurthy, K., Guru Row, T. N. & Venkatesan, K. (2002). Photochem. Photobiol. Sci. 1, 427-430.]); Davis et al. (2004[Davis, R., Abraham, S., Rath, N. P. & Das, S. (2004). New J. Chem. 28, 1368-1372.], 2008[Davis, R., Kumar, N. S. S., Abraham, S., Suresh, C. H., Rath, N. P., Tamaoki, N. & Das, S. (2008). J. Phys. Chem. C, 112, 2137-2146.]); Kumar et al. (2009[Kumar, N. S. S., Varghese, S., Suresh, C. H., Rath, N. P. & Das, S. (2009). J. Phys. Chem. C, 113, 11927-11935.]); Ono et al. (2009[Ono, K., Tokura, O. & Tomura, M. (2009). Acta Cryst. E65, o2118.]). For the synthesis and the use of the title compound in the preparation of polymers and chiral liquid crystals, see: Rotarski (1908[Rotarski, Th. (1908). Ber. Dtsch Chem. Ges. 41, 1994-1998.]); Wang et al. (2003[Wang, S. J., Tjong, S. C., Meng, Y. Z., Fung, M. K., Lee, S. T. & Hay, A. S. (2003). J. Appl. Polym. Sci. 89, 1645-1651.]); Das et al. (2008[Das, S., Narayan, G., Abraham, S., Jayaraman, N., Singh, M. K., Prasad, S. K. & Rao, D. S. S. (2008). Adv. Funct. Mater. 18, 1632-1640.]). For molecules with a herringbone arrangement, see: Koren et al. (2003[Koren, A. B., Curtis, M. D., Francis, A. H. & Kampf, J. W. (2003). J. Am. Chem. Soc. 125, 5040-5050.]).

[Scheme 1]

Experimental

Crystal data

  • C18H18O2

  • Mr = 266.32

  • Orthorhombic, P b c a

  • a = 7.3543 (3) Å

  • b = 6.2617 (3) Å

  • c = 31.3872 (13) Å

  • V = 1445.39 (11) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.08 mm-1

  • T = 293 K

  • 0.25 × 0.22 × 0.22 mm
Data collection

  • Bruker X8 APEXII CCD area-detector diffractometer

  • Absorption correction: numerical (SADABS; Sheldrick, 2006[Sheldrick, G. M. (2006). SADABS. University of Göttingen, Germany.]) Tmin = 0.981, Tmax = 0.983

  • 40427 measured reflections

  • 1658 independent reflections

  • 1287 reflections with I > 2[sigma](I)

  • Rint = 0.036
Refinement

  • R[F2 > 2[sigma](F2)] = 0.045

  • wR(F2) = 0.110

  • S = 1.08

  • 1658 reflections

  • 92 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.13 e Å-3

  • [Delta][rho]min = -0.13 e Å-3

Data collection: APEX2 (Bruker, 2001[Bruker (2001). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2001[Bruker (2001). APEX2 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: IS2575 ).

Acknowledgements

Research grants from the Department of Science and Technology (DST), Government of India, are gratefully acknowledged. This is contribution No. PPS-300 from PPS-NIIST. GN is grateful to the Council of Scientific and Industrial Research (CSIR) for a research fellowship. Funding from the National Science Foundation (MRI,CHE-0420497) for purchase of the APEXII diffractometer is also acknowledged.

References

Bruker (2001). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Das, S., Narayan, G., Abraham, S., Jayaraman, N., Singh, M. K., Prasad, S. K. & Rao, D. S. S. (2008). Adv. Funct. Mater. 18, 1632-1640.  [CrossRef]
Davis, R., Abraham, S., Rath, N. P. & Das, S. (2004). New J. Chem. 28, 1368-1372.  [CrossRef]
Davis, R., Kumar, N. S. S., Abraham, S., Suresh, C. H., Rath, N. P., Tamaoki, N. & Das, S. (2008). J. Phys. Chem. C, 112, 2137-2146.  [CrossRef]
George, M., Das, S., Ashokan, C. V., Rath, N. P. & George, M. V. (1998). Acta Cryst. C54, 1033-1036.  [CrossRef] [details]
Koren, A. B., Curtis, M. D., Francis, A. H. & Kampf, J. W. (2003). J. Am. Chem. Soc. 125, 5040-5050.  [CrossRef]
Kumar, N. S. S., Varghese, S., Suresh, C. H., Rath, N. P. & Das, S. (2009). J. Phys. Chem. C, 113, 11927-11935.  [CrossRef]
Ono, K., Tokura, O. & Tomura, M. (2009). Acta Cryst. E65, o2118.  [CrossRef] [details]
Rotarski, Th. (1908). Ber. Dtsch Chem. Ges. 41, 1994-1998.  [CrossRef]
Sheldrick, G. M. (2006). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Vishnumurthy, K., Guru Row, T. N. & Venkatesan, K. (2002). Photochem. Photobiol. Sci. 1, 427-430.  [CrossRef]
Wang, S. J., Tjong, S. C., Meng, Y. Z., Fung, M. K., Lee, S. T. & Hay, A. S. (2003). J. Appl. Polym. Sci. 89, 1645-1651.  [CrossRef]

Acta Cryst (2010). E66, o2678  [ doi:10.1107/S1600536810037141 ]

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