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Volume 68 
Part 1 
Page o24  
January 2012  

Received 29 October 2011
Accepted 29 November 2011
Online 3 December 2011

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.003 Å
R = 0.028
wR = 0.073
Data-to-parameter ratio = 7.0
Details
Open access

2-[(3S)-5-Oxooxolan-3-yl]isoindoline-1,3-dione

aDepartment of Chemistry and Chemical Engineering, Sichuan University of Arts and Science, Sichuan Key Laboratory of Characteristic Plant Development and Research, Sichuan Dazhou 635000, People's Republic of China
Correspondence e-mail: wjh686@163.com

The oxolan-2-one ring in the title compound, C12H9NO4, has an envelope conformation with the atom linking the two five-membered rings being the flap atom.

Related literature

For the synthesis of the title compound, see: Temperini et al. (2010[Temperini, A., Capperucci, A., Degl'Innocenti, A., Terlizzi, R. & Tiecco, M. (2010). Tetrahedron Lett. 51, 4121-4124.]). For the structure of the closely related compound, 2-(2,5-dioxotetrahydrofuran-3-yl)isoindoline-1,3-dione, see: Qian (2008[Qian, S.-S. (2008). Acta Cryst. E64, o1663.]).

[Scheme 1]

Experimental

Crystal data
  • C12H9NO4

  • Mr = 231.20

  • Orthorhombic, P 21 21 21

  • a = 5.7224 (3) Å

  • b = 10.5839 (5) Å

  • c = 16.8532 (10) Å

  • V = 1020.72 (9) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.12 mm-1

  • T = 296 K

  • 0.20 × 0.20 × 0.14 mm

Data collection
  • Bruker SMART CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.977, Tmax = 0.984

  • 4468 measured reflections

  • 1077 independent reflections

  • 1002 reflections with I > 2[sigma](I)

  • Rint = 0.021

Refinement
  • R[F2 > 2[sigma](F2)] = 0.028

  • wR(F2) = 0.073

  • S = 1.20

  • 1077 reflections

  • 154 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.10 e Å-3

  • [Delta][rho]min = -0.13 e Å-3

Data collection: SMART (Bruker, 2001[Bruker (2001). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2001[Bruker (2001). 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: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LH5369 ).


Acknowledgements

This work was supported by the Scientific Research Foundation of Sichuan University of Arts and Science (No. 2010A05Z).

References

Bruker (2001). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Qian, S.-S. (2008). Acta Cryst. E64, o1663.  [CSD] [CrossRef] [details]
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]
Temperini, A., Capperucci, A., Degl'Innocenti, A., Terlizzi, R. & Tiecco, M. (2010). Tetrahedron Lett. 51, 4121-4124.  [ISI] [CrossRef] [ChemPort]


Acta Cryst (2012). E68, o24  [ doi:10.1107/S160053681105135X ]

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