[Journal logo]

Volume 69 
Part 7 
Page o1136  
July 2013  

Received 17 June 2013
Accepted 18 June 2013
Online 22 June 2013

Key indicators
Single-crystal X-ray study
T = 173 K
Mean [sigma](C-C) = 0.004 Å
R = 0.044
wR = 0.145
Data-to-parameter ratio = 13.4
Details
Open access

1-Benzyl-5-ethyl-5-hydroxy-1H-pyrrol-2(5H)-one

aThe Key Laboratory for Chemical Biology of Fujian Province, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, Fujian 361005, People's Republic of China
Correspondence e-mail: yejl@xmu.edu.cn

The title compound, C13H15NO2, was obtained as a by-product in the Grignard reaction of malimide. The dihedral angle between the five-memebred ring (r.m.s. deviation = 0.005 Å) and the benzene ring is 67.20 (14)°. The benzene ring and the ethyl chain lie to the same side of the five-membered ring. In the crystal, molecules are linked by O-H...O hydrogen bonds, generating C(6) chains propagating in [010].

Related literature

For background to the Grignard reaction of malimide, see: Huang (2006[Huang, P.-Q. (2006). Synlett, pp. 1133-1149.]); He et al. (2003[He, B. Y., Wu, T. J., Yu, X. Y. & Huang, P. Q. (2003). Tetrahedron Asymmetry, 14, 2101-2108.]). For related structures, see: Goh et al. (2007[Goh, W. K., Iskander, G., Black, D. S. & Kumar, N. (2007). Tetrahedron Lett. 48, 2287-2290.]); Ma & Xie (2002[Ma, S. & Xie, H. (2002). J. Org. Chem. 67, 6575-6578.]).

[Scheme 1]

Experimental

Crystal data
  • C13H15NO2

  • Mr = 215.27

  • Monoclinic, P 21

  • a = 7.0399 (14) Å

  • b = 7.1795 (14) Å

  • c = 11.817 (2) Å

  • [beta] = 102.72 (3)°

  • V = 582.6 (2) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.08 mm-1

  • T = 173 K

  • 0.3 × 0.2 × 0.2 mm

Data collection
  • Oxford Diffraction Xcalibur (Sapphire3, Gemini ultra) diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.]) Tmin = 0.980, Tmax = 0.983

  • 3363 measured reflections

  • 1947 independent reflections

  • 1811 reflections with I > 2[sigma](I)

  • Rint = 0.054

Refinement
  • R[F2 > 2[sigma](F2)] = 0.044

  • wR(F2) = 0.145

  • S = 1.13

  • 1947 reflections

  • 145 parameters

  • 1 restraint

  • H-atom parameters constrained

  • [Delta][rho]max = 0.25 e Å-3

  • [Delta][rho]min = -0.32 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O2-H2A...O1i 0.82 1.95 2.772 (3) 176
Symmetry code: (i) [-x, y+{\script{1\over 2}}, -z+2].

Data collection: CrysAlis PRO (Oxford Diffraction, 2010[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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: SHELXTL; software used to prepare material for publication: SHELXTL.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB7096 ).


Acknowledgements

The authors thank the NSF of Fujian Province of China (2011J01056) for financial support.

References

Goh, W. K., Iskander, G., Black, D. S. & Kumar, N. (2007). Tetrahedron Lett. 48, 2287-2290.  [Web of Science] [CSD] [CrossRef] [ChemPort]
He, B. Y., Wu, T. J., Yu, X. Y. & Huang, P. Q. (2003). Tetrahedron Asymmetry, 14, 2101-2108.  [Web of Science] [CrossRef] [ChemPort]
Huang, P.-Q. (2006). Synlett, pp. 1133-1149.  [Web of Science] [CrossRef]
Ma, S. & Xie, H. (2002). J. Org. Chem. 67, 6575-6578.  [CSD] [CrossRef] [PubMed] [ChemPort]
Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]


Acta Cryst (2013). E69, o1136  [ doi:10.1107/S1600536813016887 ]

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.