(E)-3-[2,5-Dioxo-3-(propan-2-yl­idene)pyrrolidin-1-yl]acrylic acid

Miao, F.; Qin, B.-F.; Yang, L.-Z.; Yang, X.-J.; Zhou, L.

doi:10.1107/S1600536810005040

Volume 66
Part 3
Page o634
March 2010

Received 1 February 2010
Accepted 8 February 2010
Online 13 February 2010

Key indicators
Single-crystal X-ray study
T = 296 K
Mean (C-C) = 0.003 Å
R = 0.047
wR = 0.125
Data-to-parameter ratio = 13.3
Details

(E)-3-[2,5-Dioxo-3-(propan-2-ylidene)pyrrolidin-1-yl]acrylic acid

Fang Miao,^a Bao-Fu Qin,^a Li-Zhen Yang,^b Xin-Juan Yang ^a,^b and Le Zhou ^a,^b ^*

^aCollege of Life Science, Northwest A&F University, Yangling 712100, People's Republic of China, and ^bCollege of Science, Northwest A&F University, Yangling 712100, People's Republic of China
Correspondence e-mail: zhoulechem@yahoo.com.cn

The title compound, C₁₀H₁₁NO₄, was extracted from a culture broth of Penicillium verruculosum YL-52. The molecular structure is essentially planar, with an r.m.s. deviation of 0.01342 (2) Å for the non-H atoms. In the crystal structure, adjacent molecules are connected into a centrosymmetric dimer through a pair of O-HO hydrogen bonds. The dimers are further extended into a chain by weak C-HO hydrogen bonds.

Related literature

For a related structure, see: Cheng et al. (2009). For details of Penicillium verruculosum YL-52, see: Yang et al. (2009).

Experimental

Crystal data

C₁₀H₁₁NO₄
M_r = 209.20
Triclinic, $[P \overline 1]$
a = 6.5384 (14) Å
b = 7.5309 (17) Å
c = 10.405 (2) Å
= 93.009 (3)°
= 101.247 (2)°
= 90.410 (3)°
V = 501.74 (19) Å³
Z = 2
Mo K radiation
= 0.11 mm^-1
T = 296 K
0.33 × 0.12 × 0.08 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) T_min = 0.965, T_max = 0.991
3845 measured reflections
1849 independent reflections
1255 reflections with I > 2(I)
R_int = 0.024

Refinement

R[F² > 2(F²)] = 0.047
wR(F²) = 0.125
S = 1.05
1849 reflections
139 parameters
H-atom parameters constrained
_max = 0.17 e Å^-3
_min = -0.19 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O1-H1O2ⁱ	0.82	1.83	2.647 (2)	174
C6-H6AO4ⁱⁱ	0.97	2.60	3.399 (3)	140
Symmetry codes: (i) -x+3, -y+1, -z+2; (ii) -x+1, -y+2, -z+1.

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); 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) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: IS2521 ).

Acknowledgements

This work was supported by the National Natural Science Foundation of China (grant Nos. 30571402 and 30771454).

References

Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Cheng, Q., Xu, X., Liu, L. & Zhang, L. (2009). Acta Cryst. E65, o3012.
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.
Yang, L.-Z., Zhou, L., Xu, H. & Qin, B.-F. (2009). Acta Agric. Boreal. Occident. Sin. 18, 98-102.

organic compounds