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Volume 69 
Part 3 
Page o321  
March 2013  

Received 23 January 2013
Accepted 29 January 2013
Online 2 February 2013

Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.002 Å
R = 0.026
wR = 0.065
Data-to-parameter ratio = 9.7
Details
Open access

3-Methylideneoxolane-2,5-dione

aInstitut für Chemie neuer Materialien, Organische Materialchemie, Universität Osnabrück, Barbarastrasse 7, D-49069 Osnabrück, Germany, and bInstitut für Chemie neuer Materialien, Strukturchemie, Universität Osnabrück, Barbarastrasse 7, D-49069 Osnabrück, Germany
Correspondence e-mail: hreuter@uos.de

The title compound (itaconic anhydride), C5H4O3, consists of a five-membered carbon-oxygen ring in a flat envelope conformation (the unsubstituted C atom being the flap) with three exocyclic double bonds to two O atoms and one C atom. In contrast to the bond lengths, which are very similar to those in itaconic acid in its pure form or in adducts with other molecules, the bond angles differ significantly because of the effect of ring closure giving rise to strong distortions at the C atoms involved in the exocyclic double bonds. In the crystal, C-H...O interactions link the molecules, forming an extended three-dimensional network.

Related literature

For the structure of the pure acid, see: Harlow & Pfluger (1973[Harlow, R. L. & Pfluger, C. E. (1973). Acta Cryst. B29, 2965-2966.]) and for the structure of the acid in combination with 2,2'-dipyridyl-N,N'-dioxide or urea, see: Smith et al. (1997[Smith, G., Kennard, C. H. L. & Byriel, K. A. (1997). Aust. J. Chem. 50, 1021-1026.]); Baures et al. (2000[Baures, P. W., Wiznycia, A. & Beatty, A. M. (2000). Bioorg. Med. Chem. 8, 1599-1605.]). For the structure of succinic anhydride, see: Ferretti et al. (2002)[Ferretti, V., Gilli, P. & Gavezzotti, A. (2002). Chem. Eur. J. 8, 1710-1718.]. For the preparation of the anhydride, see: Choudhary (2004[Choudhary, V. (2004). private communication.]); Kempf (1909[Kempf, R. (1909). J. Prakt. Chem. (Leipzig), 78, 201-259.]) and for its polymerization, see: Otsu & Yang (1991[Otsu, T. & Yang, J.-Z. (1991). Polym. Int. 25, 245-251.]).

[Scheme 1]

Experimental

Crystal data
  • C5H4O3

  • Mr = 112.08

  • Orthorhombic, P 21 21 21

  • a = 5.4854 (3) Å

  • b = 7.3498 (5) Å

  • c = 12.1871 (7) Å

  • V = 491.34 (5) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.13 mm-1

  • T = 100 K

  • 0.27 × 0.09 × 0.07 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2009[Bruker (2009). APEX2, SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.966, Tmax = 0.991

  • 18134 measured reflections

  • 716 independent reflections

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

  • Rint = 0.037

Refinement
  • R[F2 > 2[sigma](F2)] = 0.026

  • wR(F2) = 0.065

  • S = 1.10

  • 716 reflections

  • 74 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.24 e Å-3

  • [Delta][rho]min = -0.14 e Å-3

Table 1
Selected bond angles (°)

C2-O1-C5 110.65 (11)
O1-C2-O2 119.98 (13)
O2-C2-C3 131.52 (14)
O1-C2-C3 108.49 (12)
C2-C3-C6 122.35 (13)
C4-C3-C6 130.45 (14)
C2-C3-C4 107.19 (13)
C3-C4-C5 103.29 (13)
O1-C5-O5 120.01 (14)
O5-C5-C4 129.68 (15)
O1-C5-C4 110.31 (12)

Table 2
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C6-H6A...O5i 0.95 2.73 3.645 (2) 162
C6-H6B...O5ii 0.95 2.48 3.369 (2) 155
C4-H4B...O2iii 0.99 2.57 3.433 (2) 146
C4-H4A...O2iv 0.99 2.71 3.181 (2) 109
Symmetry codes: (i) [-x+{\script{3\over 2}}, -y+2, z-{\script{1\over 2}}]; (ii) [-x+1, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]; (iii) [-x+{\script{3\over 2}}, -y+2, z+{\script{1\over 2}}]; (iv) [x-{\script{1\over 2}}, -y+{\script{3\over 2}}, -z+1].

Data collection: APEX2 (Bruker, 2009[Bruker (2009). APEX2, SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). APEX2, SADABS 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: DIAMOND (Brandenburg, 2006[Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany.]) and Mercury (Macrae et al., 2008[Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.]); 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: GG2110 ).


Acknowledgements

We thanks the Deutsche Forschungsgemeinschaft and the Government of Lower Saxony for their financial support in the acquisition of the diffractometer.

References

Baures, P. W., Wiznycia, A. & Beatty, A. M. (2000). Bioorg. Med. Chem. 8, 1599-1605.  [CSD] [CrossRef] [PubMed] [ChemPort]
Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Bruker (2009). APEX2, SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Choudhary, V. (2004). private communication.
Ferretti, V., Gilli, P. & Gavezzotti, A. (2002). Chem. Eur. J. 8, 1710-1718.  [CSD] [CrossRef] [PubMed] [ChemPort]
Harlow, R. L. & Pfluger, C. E. (1973). Acta Cryst. B29, 2965-2966.  [CrossRef] [ChemPort] [details] [ISI]
Kempf, R. (1909). J. Prakt. Chem. (Leipzig), 78, 201-259.  [CrossRef] [ChemPort]
Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.  [ISI] [CrossRef] [ChemPort] [details]
Otsu, T. & Yang, J.-Z. (1991). Polym. Int. 25, 245-251.  [CrossRef] [ChemPort] [ISI]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Smith, G., Kennard, C. H. L. & Byriel, K. A. (1997). Aust. J. Chem. 50, 1021-1026.  [ISI] [CrossRef] [ChemPort]


Acta Cryst (2013). E69, o321  [ doi:10.1107/S1600536813002924 ]

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