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

Qian, S.-S.

doi:10.1107/S1600536808024094

organic compounds

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Volume 64| Part 9| September 2008| Page o1663

doi:10.1107/S1600536808024094

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

Shao-Song Qian ^a ^*

^aSchool of Life Sciences, Shandong University of Technology, Zibo 255049, People's Republic of China
^*Correspondence e-mail: njuqss@yahoo.com.cn

(Received 25 July 2008; accepted 29 July 2008; online 6 August 2008)

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.

Related literature

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

Experimental

Crystal data

C₁₂H₇NO₅
M_r = 245.19
Monoclinic, P 2₁ /n
a = 12.129 (2) Å
b = 5.1385 (10) Å
c = 16.818 (3) Å
β = 100.21 (3)°
V = 1031.6 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.13 mm⁻¹
T = 293 (2) K
0.30 × 0.30 × 0.05 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: ψ scan (SADABS; Sheldrick, 1996 ) T_min = 0.963, T_max = 0.994
1963 measured reflections
1870 independent reflections
1492 reflections with I > 2σ(I)
R_int = 0.040
3 standard reflections every 200 reflections intensity decay: none

Refinement

R[F² > 2σ(F²)] = 0.043
wR(F²) = 0.133
S = 1.07
1870 reflections
164 parameters
H-atom parameters constrained
Δρ_max = 0.31 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C9—H9A⋯O1	0.98	2.54	2.915 (3)	103 (4)
C12—H12B⋯O5ⁱ	0.97	2.58	3.476 (3)	153 (4)
Symmetry code: (i) x, y-1, z.

Data collection: CAD-4 Software (Enraf–Nonius, 1989 ); cell refinement: CAD-4 Software; 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.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808024094/bt2757sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808024094/bt2757Isup2.hkl

checkCIF report

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.

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

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

C₁₂H₇NO₅	F(000) = 504
M_r = 245.19	D_x = 1.579 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 25 reflections
a = 12.129 (2) Å	θ = 10–13°
b = 5.1385 (10) Å	µ = 0.13 mm⁻¹
c = 16.818 (3) Å	T = 293 K
β = 100.21 (3)°	Prism, colorless
V = 1031.6 (4) Å³	0.30 × 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 tube	R_int = 0.040
Graphite monochromator	θ_max = 25.3°, θ_min = 1.9°
ω/2θ scans	h = 0→14
Absorption correction: ψ scan (SADABS; Sheldrick, 1996)	k = 0→6
T_min = 0.963, T_max = 0.994	l = −20→19
1963 measured reflections	3 standard reflections every 200 reflections
1870 independent reflections	intensity decay: none

Refinement top

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)] = 0.043	H-atom parameters constrained
wR(F²) = 0.133	w = 1/[σ²(F_o²) + (0.0585P)² + 0.7913P] where P = (F_o² + 2F_c²)/3
S = 1.07	(Δ/σ)_max < 0.001
1870 reflections	Δρ_max = 0.31 e Å⁻³
164 parameters	Δρ_min = −0.21 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: 0.055 (5)

Crystal data top

C₁₂H₇NO₅	V = 1031.6 (4) Å³
M_r = 245.19	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 12.129 (2) Å	µ = 0.13 mm⁻¹
b = 5.1385 (10) Å	T = 293 K
c = 16.818 (3) Å	0.30 × 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)	R_int = 0.040
T_min = 0.963, T_max = 0.994	3 standard reflections every 200 reflections
1963 measured reflections	intensity decay: none
1870 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.043	0 restraints
wR(F²) = 0.133	H-atom parameters constrained
S = 1.07	Δρ_max = 0.31 e Å⁻³
1870 reflections	Δρ_min = −0.21 e Å⁻³
164 parameters

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

	x	y	z	U_iso*/U_eq
N	0.76293 (16)	−0.0485 (4)	0.04496 (11)	0.0347 (5)
O1	0.88949 (15)	−0.3867 (4)	0.04821 (11)	0.0466 (5)
C1	0.9239 (2)	0.0386 (6)	−0.18134 (16)	0.0487 (7)
H1A	0.9710	0.0066	−0.2183	0.058*
O2	0.65372 (15)	0.3125 (3)	0.00935 (10)	0.0430 (5)
C2	0.8492 (2)	0.2458 (6)	−0.19425 (15)	0.0481 (7)
H2A	0.8462	0.3474	−0.2404	0.058*
C3	0.7791 (2)	0.3047 (5)	−0.14002 (14)	0.0409 (6)
H3A	0.7292	0.4436	−0.1485	0.049*
O3	0.44844 (18)	0.1302 (5)	0.13241 (15)	0.0729 (7)
O4	0.81433 (16)	0.2349 (4)	0.20434 (11)	0.0523 (6)
C4	0.78694 (19)	0.1471 (5)	−0.07286 (13)	0.0332 (6)
O5	0.62761 (15)	0.2101 (3)	0.18451 (10)	0.0424 (5)
C5	0.85913 (19)	−0.0636 (5)	−0.06052 (13)	0.0341 (6)
C6	0.9295 (2)	−0.1217 (5)	−0.11412 (15)	0.0413 (6)
H6A	0.9786	−0.2621	−0.1057	0.050*
C7	0.84523 (19)	−0.1944 (5)	0.01570 (14)	0.0339 (6)
C8	0.7244 (2)	0.1603 (5)	−0.00526 (13)	0.0338 (6)
C9	0.7191 (2)	−0.1091 (5)	0.11716 (13)	0.0339 (6)
H9A	0.7604	−0.2566	0.1449	0.041*
C10	0.7312 (2)	0.1266 (5)	0.17350 (14)	0.0388 (6)
C11	0.5426 (2)	0.0628 (6)	0.13833 (15)	0.0445 (7)
C12	0.5937 (2)	−0.1667 (5)	0.10354 (15)	0.0388 (6)
H12A	0.5639	−0.1847	0.0464	0.047*
H12B	0.5791	−0.3258	0.1309	0.047*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N	0.0446 (11)	0.0297 (10)	0.0303 (10)	0.0057 (9)	0.0077 (8)	0.0006 (8)
O1	0.0528 (11)	0.0376 (10)	0.0481 (11)	0.0136 (9)	0.0056 (8)	0.0040 (8)
C1	0.0487 (15)	0.0611 (18)	0.0394 (14)	−0.0068 (14)	0.0165 (12)	−0.0077 (14)
O2	0.0536 (11)	0.0369 (10)	0.0398 (10)	0.0133 (9)	0.0117 (8)	0.0027 (8)
C2	0.0594 (17)	0.0513 (17)	0.0336 (13)	−0.0100 (14)	0.0082 (12)	0.0012 (12)
C3	0.0535 (15)	0.0341 (13)	0.0339 (13)	−0.0014 (12)	0.0045 (11)	−0.0007 (11)
O3	0.0529 (13)	0.0827 (17)	0.0840 (16)	0.0099 (13)	0.0147 (11)	−0.0248 (14)
O4	0.0595 (12)	0.0508 (12)	0.0444 (11)	−0.0101 (10)	0.0036 (9)	−0.0093 (9)
C4	0.0392 (12)	0.0296 (12)	0.0302 (12)	−0.0021 (11)	0.0046 (10)	−0.0041 (10)
O5	0.0583 (11)	0.0337 (10)	0.0353 (9)	0.0070 (8)	0.0090 (8)	−0.0050 (7)
C5	0.0388 (12)	0.0292 (12)	0.0328 (12)	−0.0040 (10)	0.0023 (10)	−0.0057 (10)
C6	0.0406 (13)	0.0396 (14)	0.0432 (14)	0.0004 (12)	0.0061 (11)	−0.0071 (12)
C7	0.0367 (12)	0.0276 (12)	0.0351 (12)	0.0009 (11)	0.0001 (10)	−0.0051 (10)
C8	0.0411 (13)	0.0285 (12)	0.0309 (12)	0.0018 (11)	0.0036 (10)	−0.0012 (10)
C9	0.0468 (14)	0.0266 (12)	0.0287 (11)	0.0047 (11)	0.0073 (10)	0.0014 (10)
C10	0.0555 (16)	0.0324 (13)	0.0277 (12)	0.0030 (12)	0.0048 (11)	0.0021 (10)
C11	0.0523 (16)	0.0446 (16)	0.0386 (14)	0.0034 (13)	0.0135 (12)	−0.0014 (12)
C12	0.0505 (15)	0.0286 (13)	0.0386 (13)	−0.0008 (11)	0.0110 (11)	0.0002 (10)

Geometric parameters (Å, º) top

N—C8	1.394 (3)	C4—C5	1.385 (3)
N—C7	1.405 (3)	C4—C8	1.476 (3)
N—C9	1.443 (3)	O5—C10	1.370 (3)
O1—C7	1.208 (3)	O5—C11	1.398 (3)
C1—C6	1.391 (4)	C5—C6	1.380 (3)
C1—C2	1.390 (4)	C5—C7	1.483 (3)
C1—H1A	0.9300	C6—H6A	0.9300
O2—C8	1.217 (3)	C9—C12	1.526 (3)
C2—C3	1.387 (4)	C9—C10	1.529 (3)
C2—H2A	0.9300	C9—H9A	0.9800
C3—C4	1.379 (3)	C11—C12	1.499 (4)
C3—H3A	0.9300	C12—H12A	0.9700
O3—C11	1.180 (3)	C12—H12B	0.9700
O4—C10	1.188 (3)

C8—N—C7	112.40 (19)	O1—C7—C5	130.7 (2)
C8—N—C9	122.82 (19)	N—C7—C5	104.9 (2)
C7—N—C9	124.76 (19)	O2—C8—N	123.0 (2)
C6—C1—C2	121.1 (2)	O2—C8—C4	131.4 (2)
C6—C1—H1A	119.4	N—C8—C4	105.6 (2)
C2—C1—H1A	119.4	N—C9—C12	114.92 (19)
C3—C2—C1	121.6 (2)	N—C9—C10	109.97 (19)
C3—C2—H2A	119.2	C12—C9—C10	103.30 (19)
C1—C2—H2A	119.2	N—C9—H9A	109.5
C4—C3—C2	116.7 (2)	C12—C9—H9A	109.5
C4—C3—H3A	121.7	C10—C9—H9A	109.5
C2—C3—H3A	121.7	O4—C10—O5	121.5 (2)
C3—C4—C5	122.1 (2)	O4—C10—C9	128.5 (2)
C3—C4—C8	129.3 (2)	O5—C10—C9	110.0 (2)
C5—C4—C8	108.6 (2)	O3—C11—O5	119.7 (3)
C10—O5—C11	111.05 (19)	O3—C11—C12	131.2 (3)
C6—C5—C4	121.3 (2)	O5—C11—C12	109.1 (2)
C6—C5—C7	130.2 (2)	C11—C12—C9	105.0 (2)
C4—C5—C7	108.5 (2)	C11—C12—H12A	110.7
C5—C6—C1	117.2 (2)	C9—C12—H12A	110.7
C5—C6—H6A	121.4	C11—C12—H12B	110.7
C1—C6—H6A	121.4	C9—C12—H12B	110.7
O1—C7—N	124.3 (2)	H12A—C12—H12B	108.8

C6—C1—C2—C3	1.4 (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—O2	179.3 (3)
C2—C3—C4—C8	179.9 (2)	C3—C4—C8—N	178.5 (2)
C3—C4—C5—C6	1.9 (4)	C5—C4—C8—N	−0.3 (3)
C8—C4—C5—C6	−179.2 (2)	C8—N—C9—C12	59.4 (3)
C3—C4—C5—C7	−178.7 (2)	C7—N—C9—C12	−118.4 (2)
C8—C4—C5—C7	0.2 (3)	C8—N—C9—C10	−56.6 (3)
C4—C5—C6—C1	−0.7 (4)	C7—N—C9—C10	125.6 (2)
C7—C5—C6—C1	−179.9 (2)	C11—O5—C10—O4	176.2 (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—O4	175.9 (3)
C8—N—C7—C5	−0.2 (3)	N—C9—C10—O5	117.8 (2)
C9—N—C7—C5	177.9 (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—O1	178.4 (2)	C10—O5—C11—C12	9.9 (3)
C6—C5—C7—N	179.3 (2)	O3—C11—C12—C9	167.1 (3)
C4—C5—C7—N	0.0 (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—O2	2.6 (4)	C10—C9—C12—C11	10.5 (2)
C7—N—C8—C4	0.3 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9A···O1	0.98	2.54	2.915 (3)	103 (4)
C12—H12B···O5ⁱ	0.97	2.58	3.476 (3)	153 (4)

Symmetry code: (i) x, y−1, z.

Experimental details

Crystal data
Chemical formula	C₁₂H₇NO₅
M_r	245.19
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	293
a, b, c (Å)	12.129 (2), 5.1385 (10), 16.818 (3)
β (°)	100.21 (3)
V (Å³)	1031.6 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.13
Crystal size (mm)	0.30 × 0.30 × 0.05

Data collection
Diffractometer	Enraf–Nonius CAD-4 diffractometer
Absorption correction	ψ scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.963, 0.994
No. of measured, independent and observed [I > 2σ(I)] reflections	1963, 1870, 1492
R_int	0.040
(sin θ/λ)_max (Å⁻¹)	0.601

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.043, 0.133, 1.07
No. of reflections	1870
No. of parameters	164
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.31, −0.21

Computer programs: CAD-4 Software (Enraf–Nonius, 1989), XCAD4 (Harms & Wocadlo, 1995), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), XP in SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9A···O1	0.98	2.54	2.915 (3)	103 (4)
C12—H12B···O5ⁱ	0.97	2.58	3.476 (3)	153 (4)

Symmetry code: (i) x, y−1, z.

Acknowledgements

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

References

Abdel, H. & Atef, A. M. (2004). Arch. Pharm. Res. 27, 495–501. Web of Science PubMed Google Scholar
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. CrossRef Web of Science Google Scholar
Enraf–Nonius (1989). CAD-4 Software. Enraf–Nonius, Delft, The Netherlands. Google Scholar
Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany. Google Scholar
King, F. E. & Kidd, D. A. A. (1951). J. Chem. Soc. pp. 2976–2978. CrossRef Web of Science Google Scholar
Qian, S.-S., Cui, H.-Y. & Zhao, B.-S. (2006). Acta Cryst. E62, o2276–o2277. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar