2-(2,5-Dioxotetra-hydro-furan-3-yl)isoindoline-1,3-dione.

In the title compound, C(12)H(7)NO(5), 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, mol-ecules are linked through inter-molecular 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 = 245.19

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.133

S = 1.07

1870 reflections

164 parameters

H-atom parameters constrained

Δρmax = 0.31 e Å−3

Δρmin = −0.21 e Å−3

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.

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

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

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

C12H7NO5	F(000) = 504
Mr = 245.19	Dx = 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

Enraf–Nonius CAD-4 diffractometer	1492 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.040
graphite	θmax = 25.3°, θmin = 1.9°
ω/2θ scans	h = 0→14
Absorption correction: ψ scan (SADABS; Sheldrick, 1996)	k = 0→6
Tmin = 0.963, Tmax = 0.994	l = −20→19
1963 measured reflections	3 standard reflections every 200 reflections
1870 independent reflections	intensity decay: none

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(Fo2) + (0.0585P)2 + 0.7913P] where P = (Fo2 + 2Fc2)/3
S = 1.07	(Δ/σ)max < 0.001
1870 reflections	Δρmax = 0.31 e Å−3
164 parameters	Δρmin = −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)

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
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*

	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)

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)

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)

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) .