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Volume 64 
Part 3 
Page o566  
March 2008  

Received 1 December 2007
Accepted 14 January 2008
Online 6 February 2008

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.002 Å
R = 0.038
wR = 0.122
Data-to-parameter ratio = 12.7
Details
Open access

2-Acetamido-3-(4-hydroxy-3-methoxyphenyl)acrylic acid

aSchool of Chemistry and Biotechnology, Yunnan Nationalities University, Kunming 650031, People's Republic of China, and bEngineering and Research Center of Chinese Herb Modernization, Northwest University, Xi'an 710069, People's Republic of China
Correspondence e-mail: zhengxh@nwu.edu.cn

In the title compound, C12H13NO5, the azlactone of vanillin, the acrylic acid side chain has a trans extended conformation. There are intermolecular N-H...O and O-H...O hydrogen bonds in the crystal structure.

Related literature

For a related structure, see: Haasbroek et al. (1998[Haasbroek, P. P., Oliver, D. W. & Carpy, A. J. M. (1998). J. Chem. Crystallogr. 28, 193-196.]). For information on the synthesis, see: Wong et al. (1992[Wong, H. N. C., Xu, Z. L., Chang, H. M. & Lee, C. M. (1992). Synthesis, pp. 793-797.]).

[Scheme 1]

Experimental

Crystal data
  • C12H13NO5

  • Mr = 251.23

  • Orthorhombic, P b c a

  • a = 12.7573 (14) Å

  • b = 12.7518 (14) Å

  • c = 14.7290 (17) Å

  • V = 2396.1 (5) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 0.11 mm-1

  • T = 296 (2) K

  • 0.37 × 0.30 × 0.26 mm

Data collection
  • Bruker SMART CCD area-detector diffractometer

  • Absorption correction: none

  • 11011 measured reflections

  • 2122 independent reflections

  • 1788 reflections with I > 2[sigma](I)

  • Rint = 0.021

Refinement
  • R[F2 > 2[sigma](F2)] = 0.037

  • wR(F2) = 0.122

  • S = 1.01

  • 2122 reflections

  • 167 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.20 e Å-3

  • [Delta][rho]min = -0.31 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O4-H4...O3i 0.82 1.79 2.6044 (15) 171
O1-H1B...O5ii 0.82 1.84 2.6582 (13) 177
N1-H1...O1iii 0.86 2.13 2.9501 (14) 159
Symmetry codes: (i) -x, -y+2, -z; (ii) -x, -y+2, -z+1; (iii) [-x+{\script{1\over 2}}, -y+2, z-{\script{1\over 2}}].

Data collection: SMART (Bruker, 1997[Bruker (1997). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 1997[Bruker (1997). SMART 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: CF2176 ).


Acknowledgements

The authors thank the Ministry of Science and Technology of Shaanxi Province and the Ministry of Education of the People's Republic of China for financial support (grant Nos. 2006kz10-G5, 2007ZDKG-70 and 207151).

References

Bruker (1997). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Haasbroek, P. P., Oliver, D. W. & Carpy, A. J. M. (1998). J. Chem. Crystallogr. 28, 193-196.  [CrossRef] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Wong, H. N. C., Xu, Z. L., Chang, H. M. & Lee, C. M. (1992). Synthesis, pp. 793-797.  [CrossRef]


Acta Cryst (2008). E64, o566  [ doi:10.1107/S1600536808001347 ]

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