2-[(3S)-5-Oxooxolan-3-yl]isoindoline-1,3-dione.

The oxolan-2-one ring in the title compound, C(12)H(9)NO(4), has an envelope conformation with the atom linking the two five-membered rings being the flap atom.

Related literature

For the synthesis of the title compound, see: Temperini et al. (2010 ▶). For the structure of the closely related compound, 2-(2,5-dioxotetra­hydro­furan-3-yl)isoindoline-1,3-dione, see: Qian (2008 ▶).

Experimental

Crystal data

C12H9NO4

M = 231.20

Orthorhombic,

a = 5.7224 (3) Å

b = 10.5839 (5) Å

c = 16.8532 (10) Å

V = 1020.72 (9) Å3

Z = 4

Mo Kα radiation

μ = 0.12 mm−1

T = 296 K

0.20 × 0.20 × 0.14 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.977, T max = 0.984

4468 measured reflections

1077 independent reflections

1002 reflections with I > 2σ(I)

R int = 0.021

Refinement

R[F 2 > 2σ(F 2)] = 0.028

wR(F 2) = 0.073

S = 1.20

1077 reflections

154 parameters

H-atom parameters constrained

Δρmax = 0.10 e Å−3

Δρmin = −0.13 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S160053681105135X/lh5369sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681105135X/lh5369Isup2.hkl

Supplementary material file. DOI: 10.1107/S160053681105135X/lh5369Isup3.cml

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

C12H9NO4	F(000) = 480
Mr = 231.20	Dx = 1.505 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 2599 reflections
a = 5.7224 (3) Å	θ = 2.3–27.2°
b = 10.5839 (5) Å	µ = 0.12 mm−1
c = 16.8532 (10) Å	T = 296 K
V = 1020.72 (9) Å3	Block, colourless
Z = 4	0.20 × 0.20 × 0.14 mm

Bruker SMART CCD area-detector diffractometer	1077 independent reflections
Radiation source: fine-focus sealed tube	1002 reflections with I > 2σ(I)
graphite	Rint = 0.021
φ and ω scans	θmax = 25.0°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −6→6
Tmin = 0.977, Tmax = 0.984	k = −12→12
4468 measured reflections	l = −19→17

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.028	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.073	H-atom parameters constrained
S = 1.20	w = 1/[σ2(Fo2) + (0.0366P)2 + 0.0827P] where P = (Fo2 + 2Fc2)/3
1077 reflections	(Δ/σ)max < 0.001
154 parameters	Δρmax = 0.10 e Å−3
0 restraints	Δρmin = −0.13 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
C1	0.8388 (3)	0.49330 (17)	0.93941 (11)	0.0362 (4)
C2	0.6577 (4)	0.5765 (2)	0.95245 (13)	0.0445 (5)
H2	0.5424	0.5900	0.9145	0.053*
C3	0.6548 (4)	0.6395 (2)	1.02494 (13)	0.0493 (5)
H3	0.5347	0.6960	1.0360	0.059*
C4	0.8280 (4)	0.6193 (2)	1.08081 (13)	0.0501 (5)
H4	0.8220	0.6627	1.1288	0.060*
C5	1.0100 (4)	0.5361 (2)	1.06693 (13)	0.0470 (5)
H5	1.1268	0.5232	1.1044	0.056*
C6	1.0115 (3)	0.47294 (17)	0.99517 (11)	0.0365 (4)
C7	1.1748 (3)	0.37695 (18)	0.96411 (11)	0.0366 (4)
C8	0.8880 (3)	0.41079 (18)	0.87031 (11)	0.0371 (4)
C9	1.2036 (4)	0.2499 (2)	0.83890 (11)	0.0422 (5)
H9	1.3392	0.2152	0.8669	0.051*
C10	1.0378 (4)	0.1429 (2)	0.81692 (13)	0.0500 (6)
H10A	1.1173	0.0621	0.8192	0.060*
H10B	0.9051	0.1408	0.8527	0.060*
C11	0.9611 (4)	0.1714 (2)	0.73468 (13)	0.0449 (5)
C12	1.2804 (4)	0.2984 (2)	0.75729 (11)	0.0524 (6)
H12A	1.2911	0.3898	0.7575	0.063*
H12B	1.4318	0.2639	0.7432	0.063*
N1	1.0948 (3)	0.34698 (16)	0.88763 (9)	0.0351 (4)
O1	1.3448 (3)	0.33039 (14)	0.99497 (8)	0.0510 (4)
O2	0.7776 (3)	0.39782 (15)	0.80953 (9)	0.0510 (4)
O3	1.1040 (3)	0.25678 (15)	0.70162 (8)	0.0522 (4)
O4	0.8005 (3)	0.12687 (16)	0.69809 (11)	0.0653 (5)

	U11	U22	U33	U12	U13	U23
C1	0.0359 (10)	0.0372 (10)	0.0356 (10)	−0.0026 (9)	0.0013 (9)	0.0020 (8)
C2	0.0405 (11)	0.0454 (11)	0.0476 (12)	0.0047 (9)	0.0003 (10)	0.0038 (10)
C3	0.0514 (12)	0.0423 (11)	0.0543 (13)	0.0063 (11)	0.0120 (11)	−0.0014 (10)
C4	0.0613 (13)	0.0461 (11)	0.0429 (12)	0.0036 (11)	0.0050 (11)	−0.0071 (10)
C5	0.0543 (12)	0.0460 (12)	0.0406 (12)	0.0020 (10)	−0.0040 (10)	−0.0038 (9)
C6	0.0408 (9)	0.0344 (10)	0.0342 (10)	−0.0010 (8)	0.0003 (9)	0.0027 (8)
C7	0.0396 (10)	0.0371 (10)	0.0332 (10)	−0.0022 (9)	−0.0040 (9)	0.0023 (8)
C8	0.0360 (9)	0.0384 (10)	0.0369 (10)	−0.0005 (8)	−0.0034 (9)	0.0024 (8)
C9	0.0442 (10)	0.0453 (11)	0.0371 (11)	0.0112 (10)	−0.0067 (9)	−0.0038 (9)
C10	0.0698 (14)	0.0366 (11)	0.0436 (12)	0.0036 (11)	−0.0023 (11)	−0.0004 (9)
C11	0.0484 (13)	0.0404 (11)	0.0460 (12)	0.0097 (10)	−0.0052 (10)	−0.0094 (10)
C12	0.0452 (12)	0.0686 (16)	0.0435 (12)	−0.0027 (12)	0.0070 (10)	−0.0075 (11)
N1	0.0370 (8)	0.0379 (9)	0.0306 (8)	0.0039 (7)	−0.0028 (7)	−0.0008 (7)
O1	0.0515 (8)	0.0563 (9)	0.0452 (8)	0.0123 (8)	−0.0160 (8)	−0.0030 (7)
O2	0.0479 (8)	0.0621 (10)	0.0430 (8)	0.0088 (8)	−0.0144 (7)	−0.0063 (7)
O3	0.0560 (8)	0.0674 (10)	0.0331 (8)	0.0037 (9)	−0.0010 (7)	0.0007 (8)
O4	0.0620 (9)	0.0601 (10)	0.0737 (11)	0.0063 (9)	−0.0234 (10)	−0.0173 (9)

C1—C2	1.378 (3)	C8—O2	1.211 (2)
C1—C6	1.381 (3)	C8—N1	1.394 (2)
C1—C8	1.482 (3)	C9—N1	1.455 (2)
C2—C3	1.392 (3)	C9—C10	1.523 (3)
C2—H2	0.9300	C9—C12	1.532 (3)
C3—C4	1.383 (3)	C9—H9	0.9800
C3—H3	0.9300	C10—C11	1.484 (3)
C4—C5	1.384 (3)	C10—H10A	0.9700
C4—H4	0.9300	C10—H10B	0.9700
C5—C6	1.382 (3)	C11—O4	1.203 (2)
C5—H5	0.9300	C11—O3	1.340 (3)
C6—C7	1.476 (3)	C12—O3	1.446 (3)
C7—O1	1.208 (2)	C12—H12A	0.9700
C7—N1	1.404 (2)	C12—H12B	0.9700
C2—C1—C6	121.98 (18)	N1—C9—C12	113.13 (18)
C2—C1—C8	130.15 (18)	C10—C9—C12	102.07 (17)
C6—C1—C8	107.87 (16)	N1—C9—H9	109.4
C1—C2—C3	117.1 (2)	C10—C9—H9	109.4
C1—C2—H2	121.5	C12—C9—H9	109.4
C3—C2—H2	121.5	C11—C10—C9	105.11 (18)
C4—C3—C2	121.0 (2)	C11—C10—H10A	110.7
C4—C3—H3	119.5	C9—C10—H10A	110.7
C2—C3—H3	119.5	C11—C10—H10B	110.7
C3—C4—C5	121.5 (2)	C9—C10—H10B	110.7
C3—C4—H4	119.3	H10A—C10—H10B	108.8
C5—C4—H4	119.3	O4—C11—O3	121.1 (2)
C6—C5—C4	117.4 (2)	O4—C11—C10	128.7 (2)
C6—C5—H5	121.3	O3—C11—C10	110.14 (18)
C4—C5—H5	121.3	O3—C12—C9	106.29 (18)
C1—C6—C5	121.05 (19)	O3—C12—H12A	110.5
C1—C6—C7	108.61 (16)	C9—C12—H12A	110.5
C5—C6—C7	130.32 (19)	O3—C12—H12B	110.5
O1—C7—N1	124.45 (19)	C9—C12—H12B	110.5
O1—C7—C6	129.62 (19)	H12A—C12—H12B	108.7
N1—C7—C6	105.93 (15)	C8—N1—C7	111.08 (16)
O2—C8—N1	124.41 (18)	C8—N1—C9	125.97 (16)
O2—C8—C1	129.20 (18)	C7—N1—C9	122.54 (16)
N1—C8—C1	106.39 (16)	C11—O3—C12	111.18 (16)
N1—C9—C10	113.28 (16)
C6—C1—C2—C3	−0.3 (3)	C12—C9—C10—C11	−21.9 (2)
C8—C1—C2—C3	178.4 (2)	C9—C10—C11—O4	−165.3 (2)
C1—C2—C3—C4	0.4 (3)	C9—C10—C11—O3	16.2 (2)
C2—C3—C4—C5	0.0 (3)	N1—C9—C12—O3	−101.25 (19)
C3—C4—C5—C6	−0.4 (3)	C10—C9—C12—O3	20.8 (2)
C2—C1—C6—C5	−0.2 (3)	O2—C8—N1—C7	−176.92 (19)
C8—C1—C6—C5	−179.17 (18)	C1—C8—N1—C7	3.3 (2)
C2—C1—C6—C7	178.63 (17)	O2—C8—N1—C9	−4.1 (3)
C8—C1—C6—C7	−0.3 (2)	C1—C8—N1—C9	176.10 (18)
C4—C5—C6—C1	0.6 (3)	O1—C7—N1—C8	176.68 (18)
C4—C5—C6—C7	−177.97 (19)	C6—C7—N1—C8	−3.45 (19)
C1—C6—C7—O1	−177.9 (2)	O1—C7—N1—C9	3.6 (3)
C5—C6—C7—O1	0.8 (4)	C6—C7—N1—C9	−176.58 (16)
C1—C6—C7—N1	2.3 (2)	C10—C9—N1—C8	−52.5 (3)
C5—C6—C7—N1	−179.1 (2)	C12—C9—N1—C8	63.0 (2)
C2—C1—C8—O2	−0.4 (4)	C10—C9—N1—C7	119.54 (18)
C6—C1—C8—O2	178.5 (2)	C12—C9—N1—C7	−124.9 (2)
C2—C1—C8—N1	179.41 (19)	O4—C11—O3—C12	178.82 (19)
C6—C1—C8—N1	−1.7 (2)	C10—C11—O3—C12	−2.6 (2)
N1—C9—C10—C11	100.02 (19)	C9—C12—O3—C11	−12.1 (2)