[Journal logo]

Volume 69 
Part 4 
Page o534  
April 2013  

Received 26 December 2012
Accepted 8 March 2013
Online 16 March 2013

Key indicators
Single-crystal X-ray study
T = 200 K
Mean [sigma](C-C) = 0.003 Å
R = 0.052
wR = 0.182
Data-to-parameter ratio = 18.5
Details
Open access

(E)-2-Hydroxycinnamaldehyde

aDepartment of Chemistry, Kyonggi University, San 94-6, Iui-dong, Yeongtong-gu, Suwon 443-760, Republic of Korea
Correspondence e-mail: sgkim123@kyonggi.ac.kr

The asymmetric unit of the title compound, C9H8O2, contains two independent molecules, both of which are essentially planar (r.m.s. deviations = 0.0294 and 0.0284 Å). The C=C double bond is in an E conformation and the vinylaldehyde groups adopt extended conformations. In the crystal, molecules are linked by O-H...O hydrogen bonds, forming infinite chains parallel to [101].

Related literature

For the synthesis of the title compound, see: Kim et al. (2004[Kim, J. H., Lee, S., Kwon, M.-G., Park, Y. S., Choi, S.-K. & Kwon, B.-M. (2004). Synth. Commun. 34, 1223-1228.]); Zeiter & Rose (2009[Zeiter, K. & Rose, C. A. (2009). J. Org. Chem. 74, 1759-1762.]). For the biological activity of 2-hydroxycinnamaldehydes, see: Kwon et al. (1996[Kwon, B. M., Cho, Y. K., Lee, S. H., Nam, J. Y., Bok, S. H., Chun, S. K., Kim, J. A. & Lee, I. R. (1996). Planta Med. 62, 183-184.]); Lee et al. (1999[Lee, C. W., Hong, D. H., Han, S. B., Park, S. H., Kim, H. K., Kwon, B. M. & Kim, H. M. (1999). Planta Med. 65, 263-264.]); Ka et al. (2003[Ka, H., Park, H. J., Jung, H. J., Choi, J. W., Cho, K. S., Ha, J. & Lee, K. T. (2003). Cancer Lett. 196, 143-152.]). For applications of 2-hydroxycinnamaldehydes, see: Zu et al. (2009[Zu, L., Zhang, S., Xie, H. & Wang, W. (2009). Org. Lett. 11, 1627-1630.]); Choi & Kim (2010[Choi, K.-S. & Kim, S.-G. (2010). Tetrahedron Lett. 51, 5203-5206.]); Lee & Kim (2011[Lee, Y. & Kim, S.-G. (2011). Bull. Korean Chem. Soc. 32, 311-314.]).

[Scheme 1]

Experimental

Crystal data
  • C9H8O2

  • Mr = 148.15

  • Monoclinic, P 21 /c

  • a = 10.1192 (15) Å

  • b = 13.7078 (19) Å

  • c = 10.9891 (15) Å

  • [beta] = 102.537 (3)°

  • V = 1488.0 (4) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 0.09 mm-1

  • T = 200 K

  • 0.40 × 0.34 × 0.29 mm

Data collection
  • Bruker SMART APEX CCD diffractometer

  • 10982 measured reflections

  • 3725 independent reflections

  • 1785 reflections with I > 2[sigma](I)

  • Rint = 0.041

Refinement
  • R[F2 > 2[sigma](F2)] = 0.052

  • wR(F2) = 0.182

  • S = 0.97

  • 3725 reflections

  • 201 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.22 e Å-3

  • [Delta][rho]min = -0.27 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O3-H3A...O2i 0.84 1.90 2.7260 (19) 166
O1-H1A...O4ii 0.84 1.90 2.7193 (19) 166
Symmetry codes: (i) x, y+1, z-1; (ii) x+1, y-1, z.

Data collection: SMART (Bruker, 2007[Bruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). SMART and SAINT. 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: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); software used to prepare material for publication: SHELXTL and publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: FY2086 ).


Acknowledgements

This work was supported by Kyonggi University Research Grant 2012.

References

Bruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Choi, K.-S. & Kim, S.-G. (2010). Tetrahedron Lett. 51, 5203-5206.  [ISI] [CrossRef] [ChemPort]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Ka, H., Park, H. J., Jung, H. J., Choi, J. W., Cho, K. S., Ha, J. & Lee, K. T. (2003). Cancer Lett. 196, 143-152.  [ISI] [CrossRef] [PubMed] [ChemPort]
Kim, J. H., Lee, S., Kwon, M.-G., Park, Y. S., Choi, S.-K. & Kwon, B.-M. (2004). Synth. Commun. 34, 1223-1228.  [ChemPort]
Kwon, B. M., Cho, Y. K., Lee, S. H., Nam, J. Y., Bok, S. H., Chun, S. K., Kim, J. A. & Lee, I. R. (1996). Planta Med. 62, 183-184.  [CrossRef] [PubMed] [ChemPort] [ISI]
Lee, C. W., Hong, D. H., Han, S. B., Park, S. H., Kim, H. K., Kwon, B. M. & Kim, H. M. (1999). Planta Med. 65, 263-264.  [ISI] [CrossRef] [PubMed] [ChemPort]
Lee, Y. & Kim, S.-G. (2011). Bull. Korean Chem. Soc. 32, 311-314.  [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [ISI] [CrossRef] [ChemPort] [details]
Zeiter, K. & Rose, C. A. (2009). J. Org. Chem. 74, 1759-1762.  [PubMed]
Zu, L., Zhang, S., Xie, H. & Wang, W. (2009). Org. Lett. 11, 1627-1630.  [ISI] [CSD] [CrossRef] [PubMed] [ChemPort]


Acta Cryst (2013). E69, o534  [ doi:10.1107/S1600536813006648 ]

This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.