3-Methyl­ideneoxolane-2,5-dione

Beginn, U.; Frosinn, M.; Reichelt, M.; Reuter, H.

doi:10.1107/S1600536813002924

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 (C-C) = 0.002 Å
R = 0.026
wR = 0.065
Data-to-parameter ratio = 9.7
Details

3-Methylideneoxolane-2,5-dione

Uwe Beginn,^a Martin Frosinn,^a Martin Reichelt ^b and Hans Reuter ^b ^*

^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-HO interactions link the molecules, forming an extended three-dimensional network.

Related literature

For the structure of the pure acid, see: Harlow & Pfluger (1973) and for the structure of the acid in combination with 2,2'-dipyridyl-N,N'-dioxide or urea, see: Smith et al. (1997); Baures et al. (2000). For the structure of succinic anhydride, see: Ferretti et al. (2002). For the preparation of the anhydride, see: Choudhary (2004); Kempf (1909) and for its polymerization, see: Otsu & Yang (1991).

Experimental

Crystal data

C₅H₄O₃
M_r = 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 radiation
= 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) T_min = 0.966, T_max = 0.991
18134 measured reflections
716 independent reflections
639 reflections with I > 2(I)
R_int = 0.037

Refinement

R[F² > 2(F²)] = 0.026
wR(F²) = 0.065
S = 1.10
716 reflections
74 parameters
H-atom parameters constrained
_max = 0.24 e Å^-3
_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-HA	D-H	HA	DA	D-HA
C6-H6AO5ⁱ	0.95	2.73	3.645 (2)	162
C6-H6BO5ⁱⁱ	0.95	2.48	3.369 (2)	155
C4-H4BO2ⁱⁱⁱ	0.99	2.57	3.433 (2)	146
C4-H4AO2^iv	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); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 2006) and Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

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.
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.
Harlow, R. L. & Pfluger, C. E. (1973). Acta Cryst. B29, 2965-2966.
Kempf, R. (1909). J. Prakt. Chem. (Leipzig), 78, 201-259.
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.
Otsu, T. & Yang, J.-Z. (1991). Polym. Int. 25, 245-251.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Smith, G., Kennard, C. H. L. & Byriel, K. A. (1997). Aust. J. Chem. 50, 1021-1026.

organic compounds