3-Methyl-ideneoxolane-2,5-dione.

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 mol-ecules, 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 inter-actions link the mol-ecules, 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 = 112.08

Orthorhombic,

a = 5.4854 (3) Å

b = 7.3498 (5) Å

c = 12.1871 (7) Å

V = 491.34 (5) Å3

Z = 4

Mo Kα radiation

μ = 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 > 2σ(I)

R int = 0.037

Refinement

R[F 2 > 2σ(F 2)] = 0.026

wR(F 2) = 0.065

S = 1.10

716 reflections

74 parameters

H-atom parameters constrained

Δρmax = 0.24 e Å−3

Δρmin = −0.14 e Å−3

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 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813002924/gg2110sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813002924/gg2110Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813002924/gg2110Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C5H4O3	Dx = 1.515 Mg m−3
Mr = 112.08	Melting point: 340.05 K
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 6479 reflections
a = 5.4854 (3) Å	θ = 3.2–27.0°
b = 7.3498 (5) Å	µ = 0.13 mm−1
c = 12.1871 (7) Å	T = 100 K
V = 491.34 (5) Å3	Needle, colourless
Z = 4	0.27 × 0.09 × 0.07 mm
F(000) = 232

Bruker APEXII CCD diffractometer	716 independent reflections
Radiation source: fine-focus sealed tube	639 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.037
φ and ω scans	θmax = 28.0°, θmin = 3.2°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −7→7
Tmin = 0.966, Tmax = 0.991	k = −9→9
18134 measured reflections	l = −16→16

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.026	H-atom parameters constrained
wR(F2) = 0.065	w = 1/[σ2(Fo2) + (0.0343P)2 + 0.0728P] where P = (Fo2 + 2Fc2)/3
S = 1.10	(Δ/σ)max < 0.001
716 reflections	Δρmax = 0.24 e Å−3
74 parameters	Δρmin = −0.14 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.037 (9)

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq
O1	1.00411 (19)	0.79021 (13)	0.61376 (8)	0.0188 (3)
C2	0.8967 (3)	0.9113 (2)	0.54015 (12)	0.0163 (3)
O2	0.99390 (19)	0.94361 (14)	0.45473 (8)	0.0224 (3)
C3	0.6656 (3)	0.9775 (2)	0.58826 (12)	0.0154 (3)
C4	0.6393 (3)	0.8894 (2)	0.69856 (12)	0.0173 (3)
H4A	0.4873	0.8171	0.7028	0.021*
H4B	0.6390	0.9814	0.7579	0.021*
C5	0.8600 (3)	0.7691 (2)	0.70585 (12)	0.0194 (3)
O5	0.9200 (2)	0.66606 (17)	0.77659 (9)	0.0299 (3)
C6	0.5202 (3)	1.0912 (2)	0.53599 (12)	0.0203 (3)
H6A	0.5626	1.1335	0.4648	0.024*
H6B	0.3731	1.1309	0.5695	0.024*

	U11	U22	U33	U12	U13	U23
O1	0.0164 (5)	0.0215 (5)	0.0185 (5)	0.0036 (5)	0.0003 (5)	−0.0016 (4)
C2	0.0165 (7)	0.0155 (7)	0.0168 (7)	−0.0018 (6)	−0.0029 (6)	−0.0029 (6)
O2	0.0215 (6)	0.0279 (6)	0.0176 (5)	−0.0033 (5)	0.0038 (6)	−0.0018 (4)
C3	0.0143 (7)	0.0157 (7)	0.0163 (6)	−0.0021 (6)	−0.0004 (6)	−0.0040 (6)
C4	0.0172 (7)	0.0176 (7)	0.0171 (6)	0.0001 (6)	0.0005 (6)	−0.0006 (6)
C5	0.0206 (8)	0.0212 (8)	0.0166 (7)	0.0006 (7)	−0.0012 (7)	−0.0036 (6)
O5	0.0335 (7)	0.0330 (7)	0.0231 (6)	0.0123 (6)	−0.0013 (5)	0.0077 (5)
C6	0.0177 (7)	0.0187 (7)	0.0245 (7)	−0.0005 (7)	−0.0009 (7)	0.0011 (6)

O1—C5	1.382 (2)	C4—C5	1.502 (2)
O1—C2	1.394 (2)	C4—H4A	0.9900
C2—O2	1.193 (2)	C4—H4B	0.9900
C2—C3	1.479 (2)	C5—O5	1.194 (2)
C3—C6	1.319 (2)	C6—H6A	0.9500
C3—C4	1.499 (2)	C6—H6B	0.9500
C2—O1—C5	110.65 (11)	O1—C5—C4	110.31 (12)
O1—C2—O2	119.98 (13)	C3—C4—H4A	111.1
O2—C2—C3	131.52 (14)	C5—C4—H4A	111.1
O1—C2—C3	108.49 (12)	C3—C4—H4B	111.1
C2—C3—C6	122.35 (13)	C5—C4—H4B	111.1
C4—C3—C6	130.45 (14)	H4A—C4—H4B	109.1
C2—C3—C4	107.19 (13)	C3—C6—H6A	120.0
C3—C4—C5	103.29 (13)	C3—C6—H6B	120.0
O1—C5—O5	120.01 (14)	H6A—C6—H6B	120.0
O5—C5—C4	129.68 (15)
O1—C2—C3—C4	0.65 (15)	C4—C5—O1—C2	−2.28 (16)
C2—C3—C4—C5	−1.86 (15)	C5—O1—C2—C3	1.00 (15)
C3—C4—C5—O1	2.54 (16)

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

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) ; (ii) ; (iii) ; (iv) .