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Volume 68 
Part 1 
Page o78  
January 2012  

Received 13 October 2011
Accepted 30 November 2011
Online 10 December 2011

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.004 Å
R = 0.061
wR = 0.178
Data-to-parameter ratio = 15.2
Details
Open access

Hexyl (E)-3-(3,4-dihydroxyphenyl)acrylate

aSchool of Biological and Chemical Engineering, Jiangsu University of Science and Technology, Zhenjiang 212018, People's Republic of China, and bSericultural Research Institute, Chinese Academy of Agricultural Sciences, Zhenjiang 212018, People's Republic of China
Correspondence e-mail: fuword@163.com

The title molecule, C15H20O4, has an E conformation about its C=C bond and is almost planar (r.m.s. deviation of all non-H atoms = 0.04 Å). The crystal structurere features O-H...O and C-H...O hydrogen bonds.

Related literature

For general background to caffeic acid and its derivatives, see: Buzzi et al. (2009[Buzzi, F. de C., Franzoi, C. L., Antonini, G., Fracasso, M., Filho, V. C., Yunes, R. A. & Niero, R. (2009). Eur. J. Med. Chem. 44, 4596-4602.]); Uwai et al. (2008[Uwai, K., Osanai, Y., Imaizumi, T., Kanno, S., Takeshita, M. & Ishikawa, M. (2008). Bioorg. Med. Chem. 16, 7795-7803.]). For details of the synthesis, see: Feng et al. (2011[Feng, Y., Zhang, A., Li, J. & He, B. (2011). Bioresource Technol. 102, 3607-3609.]); Son et al. (2011[Son, S. M., Kimura, H. & Kusakabe, K. (2011). Bioresource Technol. 102, 2130-2132.]). For related structures, see: Xia et al. (2004[Xia, C.-N., Hu, W.-X. & Rao, G.-W. (2004). Acta Cryst. E60, o913-o914.], 2006[Xia, C.-N., Hu, W.-X. & Zhou, W. (2006). Acta Cryst. E62, o3900-o3901.]). 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
  • C15H20O4

  • Mr = 264.31

  • Triclinic, [P \overline 1]

  • a = 5.2920 (11) Å

  • b = 10.689 (2) Å

  • c = 12.732 (3) Å

  • [alpha] = 95.45 (3)°

  • [beta] = 92.76 (3)°

  • [gamma] = 96.84 (3)°

  • V = 710.6 (2) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.09 mm-1

  • T = 293 K

  • 0.20 × 0.10 × 0.10 mm

Data collection
  • Enraf-Nonius CAD-4 diffractometer

  • Absorption correction: [psi] scan (North et al., 1968[North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351-359.]) Tmin = 0.983, Tmax = 0.991

  • 2912 measured reflections

  • 2608 independent reflections

  • 1515 reflections with I > 2[sigma](I)

  • Rint = 0.022

  • 3 standard reflections every 200 reflections intensity decay: 1%

Refinement
  • R[F2 > 2[sigma](F2)] = 0.061

  • wR(F2) = 0.178

  • S = 1.00

  • 2608 reflections

  • 172 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.19 e Å-3

  • [Delta][rho]min = -0.28 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O1-H1A...O2i 0.85 2.07 2.857 (2) 154
O2-H2A...O3ii 0.82 1.97 2.786 (3) 173
C5-H5A...O3ii 0.93 2.54 3.243 (3) 133
Symmetry codes: (i) -x+1, -y, -z+1; (ii) -x, -y+1, -z+1.

Data collection: CAD-4 EXPRESS (Enraf-Nonius, 1994[Enraf-Nonius (1994). CAD-4 EXPRESS. Enraf-Nonius, Delft, The Netherlands.]); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995[Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany.]); 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: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: AA2034 ).


Acknowledgements

This work was sponsored by the Qing Lan Project of Jiangsu Province, the Natural Science Foundation of Jiangsu Province (BK2009213), the College Natural Science Research Project of Jiangsu Province (08KJB530002), the Science and Technology Support Program of Jiangsu Province (BE2010419), the Start Project for Introducing Talent of Jiangsu University of Science and Technology (35211002), the Pre-research for NSFC Project of Jiangsu University of Science and Technology (33201002), and the earmarked fund for Modern Agro-industry Technology Research System (CARS-22).

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.
Buzzi, F. de C., Franzoi, C. L., Antonini, G., Fracasso, M., Filho, V. C., Yunes, R. A. & Niero, R. (2009). Eur. J. Med. Chem. 44, 4596-4602.  [PubMed] [ChemPort]
Enraf-Nonius (1994). CAD-4 EXPRESS. Enraf-Nonius, Delft, The Netherlands.
Feng, Y., Zhang, A., Li, J. & He, B. (2011). Bioresource Technol. 102, 3607-3609.  [CrossRef] [ChemPort]
Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany.
North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351-359.  [CrossRef] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Son, S. M., Kimura, H. & Kusakabe, K. (2011). Bioresource Technol. 102, 2130-2132.  [CrossRef] [ChemPort]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]
Uwai, K., Osanai, Y., Imaizumi, T., Kanno, S., Takeshita, M. & Ishikawa, M. (2008). Bioorg. Med. Chem. 16, 7795-7803.  [CrossRef] [PubMed] [ChemPort]
Xia, C.-N., Hu, W.-X. & Rao, G.-W. (2004). Acta Cryst. E60, o913-o914.  [CSD] [CrossRef] [details]
Xia, C.-N., Hu, W.-X. & Zhou, W. (2006). Acta Cryst. E62, o3900-o3901.  [CSD] [CrossRef] [details]


Acta Cryst (2012). E68, o78  [ doi:10.1107/S1600536811051671 ]

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