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Acta Cryst. (2008). E64, o1663    [ doi:10.1107/S1600536808024094 ]

2-(2,5-Dioxotetrahydrofuran-3-yl)isoindoline-1,3-dione

S.-S. Qian

Abstract top

In the title compound, C12H7NO5, the dihedral angle between the isoindole-1,3-dione plane and the least-squares plane of the furan ring is 89.2 (2)°. In the crystal structure, molecules are linked through intermolecular C-H...O hydrogen bonds, forming centrosymmetric dimers.

Comment top

The title compound has attracted attention for its anticonvulsant activity (Abdel & Atef, 2004). In addition, it was an intermediate for the synthesis of aspartic acid (King & Kidd, 1951). Here, we report its crystal structure.

The dihedral angle between the isoindole-1,3-dione plane and the plane of cyclopentane-1,3-dione is 90.0 (2)°. All the bond lengths are within normal ranges (Allen et al., 1987) and comparable to the values observed in other similar compounds (Qian et al., 2006). In the crystal structure, the molecules are linked through intermolecular C–H···O hydrogen bonds, forming centrosymmetric dimers.

Related literature top

For related literature, see: Abdel & Atef (2004); Allen et al. (1987); King & Kidd (1951); Qian et al. (2006).

Experimental top

The title compound was synthesized according to a literature method (Qian et al., 2006). L-aspartic acid (13.3 g, 0.1 mol) reacted with N-carboethoxy phthalimide (21.9 g, 0.1 mol) in 200 ml of water and 23.3 g (0.21 mol) of sodium carbonate. As a result, 21.3 g of the N-phthaloyl-L-aspartic acid was obtained (yield, 81%). 10.8 g of the title compound was obtained through heating of N-phthaloyl-L-aspartic acid (13.2 g, 0.05 mol) in 30 ml of acetic anhydride under reflux for 20 minutes. Subsequently, 0.1 g of the title compound was dissolved in acetic acid (20 ml). Single crystals suitable for X-ray diffraction were obtained by spontaneous evaporation of the solvent.

Refinement top

All H atoms were geometrically positioned and constrained to ride on their parent atoms with C—H distance in the range 0.93–0.98 Å, with Uiso(H) = 1.2Ueq(C).

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software (Enraf–Nonius, 1989); data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The structure of the title compound, showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 35% probability level.
2-(2,5-Dioxotetrahydrofuran-3-yl)isoindoline-1,3-dione top
Crystal data top
C12H7NO5F(000) = 504
Mr = 245.19Dx = 1.579 Mg m−3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 25 reflections
a = 12.129 (2) Åθ = 10–13°
b = 5.1385 (10) ŵ = 0.13 mm−1
c = 16.818 (3) ÅT = 293 K
β = 100.21 (3)°Prism, colorless
V = 1031.6 (4) Å30.30 × 0.30 × 0.05 mm
Z = 4
Data collection top
Enraf–Nonius CAD-4
diffractometer		1492 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.040
graphiteθmax = 25.3°, θmin = 1.9°
ω/2θ scansh = 0→14
Absorption correction: ψ scan
(SADABS; Sheldrick, 1996)		k = 0→6
Tmin = 0.963, Tmax = 0.994l = −20→19
1963 measured reflections3 standard reflections every 200 reflections
1870 independent reflections intensity decay: none
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.043H-atom parameters constrained
wR(F2) = 0.133 w = 1/[σ2(Fo2) + (0.0585P)2 + 0.7913P]
where P = (Fo2 + 2Fc2)/3
S = 1.07(Δ/σ)max < 0.001
1870 reflectionsΔρmax = 0.31 e Å−3
164 parametersΔρmin = −0.21 e Å−3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.055 (5)
Crystal data top
C12H7NO5V = 1031.6 (4) Å3
Mr = 245.19Z = 4
Monoclinic, P21/nMo Kα radiation
a = 12.129 (2) ŵ = 0.13 mm−1
b = 5.1385 (10) ÅT = 293 K
c = 16.818 (3) Å0.30 × 0.30 × 0.05 mm
β = 100.21 (3)°
Data collection top
Enraf–Nonius CAD-4
diffractometer		1492 reflections with I > 2σ(I)
Absorption correction: ψ scan
(SADABS; Sheldrick, 1996)		Rint = 0.040
Tmin = 0.963, Tmax = 0.994θmax = 25.3°
1963 measured reflections3 standard reflections every 200 reflections
1870 independent reflections intensity decay: none
Refinement top
R[F2 > 2σ(F2)] = 0.043H-atom parameters constrained
wR(F2) = 0.133Δρmax = 0.31 e Å−3
S = 1.07Δρmin = −0.21 e Å−3
1870 reflectionsAbsolute structure: ?
164 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N0.76293 (16)−0.0485 (4)0.04496 (11)0.0347 (5)
O10.88949 (15)−0.3867 (4)0.04821 (11)0.0466 (5)
C10.9239 (2)0.0386 (6)−0.18134 (16)0.0487 (7)
H1A0.97100.0066−0.21830.058*
O20.65372 (15)0.3125 (3)0.00935 (10)0.0430 (5)
C20.8492 (2)0.2458 (6)−0.19425 (15)0.0481 (7)
H2A0.84620.3474−0.24040.058*
C30.7791 (2)0.3047 (5)−0.14002 (14)0.0409 (6)
H3A0.72920.4436−0.14850.049*
O30.44844 (18)0.1302 (5)0.13241 (15)0.0729 (7)
O40.81433 (16)0.2349 (4)0.20434 (11)0.0523 (6)
C40.78694 (19)0.1471 (5)−0.07286 (13)0.0332 (6)
O50.62761 (15)0.2101 (3)0.18451 (10)0.0424 (5)
C50.85913 (19)−0.0636 (5)−0.06052 (13)0.0341 (6)
C60.9295 (2)−0.1217 (5)−0.11412 (15)0.0413 (6)
H6A0.9786−0.2621−0.10570.050*
C70.84523 (19)−0.1944 (5)0.01570 (14)0.0339 (6)
C80.7244 (2)0.1603 (5)−0.00526 (13)0.0338 (6)
C90.7191 (2)−0.1091 (5)0.11716 (13)0.0339 (6)
H9A0.7604−0.25660.14490.041*
C100.7312 (2)0.1266 (5)0.17350 (14)0.0388 (6)
C110.5426 (2)0.0628 (6)0.13833 (15)0.0445 (7)
C120.5937 (2)−0.1667 (5)0.10354 (15)0.0388 (6)
H12A0.5639−0.18470.04640.047*
H12B0.5791−0.32580.13090.047*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N0.0446 (11)0.0297 (10)0.0303 (10)0.0057 (9)0.0077 (8)0.0006 (8)
O10.0528 (11)0.0376 (10)0.0481 (11)0.0136 (9)0.0056 (8)0.0040 (8)
C10.0487 (15)0.0611 (18)0.0394 (14)−0.0068 (14)0.0165 (12)−0.0077 (14)
O20.0536 (11)0.0369 (10)0.0398 (10)0.0133 (9)0.0117 (8)0.0027 (8)
C20.0594 (17)0.0513 (17)0.0336 (13)−0.0100 (14)0.0082 (12)0.0012 (12)
C30.0535 (15)0.0341 (13)0.0339 (13)−0.0014 (12)0.0045 (11)−0.0007 (11)
O30.0529 (13)0.0827 (17)0.0840 (16)0.0099 (13)0.0147 (11)−0.0248 (14)
O40.0595 (12)0.0508 (12)0.0444 (11)−0.0101 (10)0.0036 (9)−0.0093 (9)
C40.0392 (12)0.0296 (12)0.0302 (12)−0.0021 (11)0.0046 (10)−0.0041 (10)
O50.0583 (11)0.0337 (10)0.0353 (9)0.0070 (8)0.0090 (8)−0.0050 (7)
C50.0388 (12)0.0292 (12)0.0328 (12)−0.0040 (10)0.0023 (10)−0.0057 (10)
C60.0406 (13)0.0396 (14)0.0432 (14)0.0004 (12)0.0061 (11)−0.0071 (12)
C70.0367 (12)0.0276 (12)0.0351 (12)0.0009 (11)0.0001 (10)−0.0051 (10)
C80.0411 (13)0.0285 (12)0.0309 (12)0.0018 (11)0.0036 (10)−0.0012 (10)
C90.0468 (14)0.0266 (12)0.0287 (11)0.0047 (11)0.0073 (10)0.0014 (10)
C100.0555 (16)0.0324 (13)0.0277 (12)0.0030 (12)0.0048 (11)0.0021 (10)
C110.0523 (16)0.0446 (16)0.0386 (14)0.0034 (13)0.0135 (12)−0.0014 (12)
C120.0505 (15)0.0286 (13)0.0386 (13)−0.0008 (11)0.0110 (11)0.0002 (10)
Geometric parameters (Å, °) top
N—C81.394 (3)C4—C51.385 (3)
N—C71.405 (3)C4—C81.476 (3)
N—C91.443 (3)O5—C101.370 (3)
O1—C71.208 (3)O5—C111.398 (3)
C1—C61.391 (4)C5—C61.380 (3)
C1—C21.390 (4)C5—C71.483 (3)
C1—H1A0.9300C6—H6A0.9300
O2—C81.217 (3)C9—C121.526 (3)
C2—C31.387 (4)C9—C101.529 (3)
C2—H2A0.9300C9—H9A0.9800
C3—C41.379 (3)C11—C121.499 (4)
C3—H3A0.9300C12—H12A0.9700
O3—C111.180 (3)C12—H12B0.9700
O4—C101.188 (3)
C8—N—C7112.40 (19)O1—C7—C5130.7 (2)
C8—N—C9122.82 (19)N—C7—C5104.9 (2)
C7—N—C9124.76 (19)O2—C8—N123.0 (2)
C6—C1—C2121.1 (2)O2—C8—C4131.4 (2)
C6—C1—H1A119.4N—C8—C4105.6 (2)
C2—C1—H1A119.4N—C9—C12114.92 (19)
C3—C2—C1121.6 (2)N—C9—C10109.97 (19)
C3—C2—H2A119.2C12—C9—C10103.30 (19)
C1—C2—H2A119.2N—C9—H9A109.5
C4—C3—C2116.7 (2)C12—C9—H9A109.5
C4—C3—H3A121.7C10—C9—H9A109.5
C2—C3—H3A121.7O4—C10—O5121.5 (2)
C3—C4—C5122.1 (2)O4—C10—C9128.5 (2)
C3—C4—C8129.3 (2)O5—C10—C9110.0 (2)
C5—C4—C8108.6 (2)O3—C11—O5119.7 (3)
C10—O5—C11111.05 (19)O3—C11—C12131.2 (3)
C6—C5—C4121.3 (2)O5—C11—C12109.1 (2)
C6—C5—C7130.2 (2)C11—C12—C9105.0 (2)
C4—C5—C7108.5 (2)C11—C12—H12A110.7
C5—C6—C1117.2 (2)C9—C12—H12A110.7
C5—C6—H6A121.4C11—C12—H12B110.7
C1—C6—H6A121.4C9—C12—H12B110.7
O1—C7—N124.3 (2)H12A—C12—H12B108.8
C6—C1—C2—C31.4 (4)C9—N—C8—C4−177.8 (2)
C1—C2—C3—C4−0.2 (4)C3—C4—C8—O2−1.9 (4)
C2—C3—C4—C5−1.5 (4)C5—C4—C8—O2179.3 (3)
C2—C3—C4—C8179.9 (2)C3—C4—C8—N178.5 (2)
C3—C4—C5—C61.9 (4)C5—C4—C8—N−0.3 (3)
C8—C4—C5—C6−179.2 (2)C8—N—C9—C1259.4 (3)
C3—C4—C5—C7−178.7 (2)C7—N—C9—C12−118.4 (2)
C8—C4—C5—C70.2 (3)C8—N—C9—C10−56.6 (3)
C4—C5—C6—C1−0.7 (4)C7—N—C9—C10125.6 (2)
C7—C5—C6—C1−179.9 (2)C11—O5—C10—O4176.2 (2)
C2—C1—C6—C5−1.0 (4)C11—O5—C10—C9−2.7 (3)
C8—N—C7—O1−178.7 (2)N—C9—C10—O4−61.0 (3)
C9—N—C7—O1−0.7 (4)C12—C9—C10—O4175.9 (3)
C8—N—C7—C5−0.2 (3)N—C9—C10—O5117.8 (2)
C9—N—C7—C5177.9 (2)C12—C9—C10—O5−5.3 (2)
C6—C5—C7—O1−2.3 (4)C10—O5—C11—O3−170.0 (3)
C4—C5—C7—O1178.4 (2)C10—O5—C11—C129.9 (3)
C6—C5—C7—N179.3 (2)O3—C11—C12—C9167.1 (3)
C4—C5—C7—N0.0 (2)O5—C11—C12—C9−12.7 (3)
C7—N—C8—O2−179.4 (2)N—C9—C12—C11−109.3 (2)
C9—N—C8—O22.6 (4)C10—C9—C12—C1110.5 (2)
C7—N—C8—C40.3 (3)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C9—H9A···O10.982.542.915 (3)103 (4)
C12—H12B···O5i0.972.583.476 (3)153 (4)
Symmetry codes: (i) x, y−1, z.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C9—H9A···O10.982.542.915 (3)103 (4)
C12—H12B···O5i0.972.583.476 (3)153 (4)
Symmetry codes: (i) x, y−1, z.
Acknowledgements top

This project was sponsored by the Doctoral Research Foundation (Shandong University of Technology, People's Republic of China).

references
References top

Abdel, H. & Atef, A. M. (2004). Arch. Pharm. Res. 27, 495–501.

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19.

Enraf–Nonius (1989). CAD-4 Software. Enraf–Nonius, Delft, The Netherlands.

Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany.

King, F. E. & Kidd, D. A. A. (1951). J. Chem. Soc. pp. 2976–2978.

Qian, S.-S., Cui, H.-Y. & Zhao, B.-S. (2006). Acta Cryst. E62, o2276–o2277.

Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.

Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.