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

Lan, X.-B.; Nan, Y.-F.; Chen, L.; Wang, S.-X.; Zheng, X.-H.

doi:10.1107/S1600536808001347

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 (C-C) = 0.002 Å
R = 0.038
wR = 0.122
Data-to-parameter ratio = 12.7
Details

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

Xiao-Bing Lan,^a,^b Ye-Fei Nan,^b Lin Chen,^a Shi-Xiang Wang ^b and Xiao-Hui Zheng ^a,^b ^*

^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-HO and O-HO hydrogen bonds in the crystal structure.

Related literature

For a related structure, see: Haasbroek et al. (1998). For information on the synthesis, see: Wong et al. (1992).

Experimental

Crystal data

C₁₂H₁₃NO₅
M_r = 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 radiation
= 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(I)
R_int = 0.021

Refinement

R[F² > 2(F²)] = 0.037
wR(F²) = 0.122
S = 1.01
2122 reflections
167 parameters
H-atom parameters constrained
_max = 0.20 e Å^-3
_min = -0.31 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O4-H4O3ⁱ	0.82	1.79	2.6044 (15)	171
O1-H1BO5ⁱⁱ	0.82	1.84	2.6582 (13)	177
N1-H1O1ⁱⁱⁱ	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); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); 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.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Wong, H. N. C., Xu, Z. L., Chang, H. M. & Lee, C. M. (1992). Synthesis, pp. 793-797.

organic compounds