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

Wang, H.; Liu, C.; Luo, F.

doi:10.1107/S160053681105135X

organic compounds

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ISSN: 2056-9890

Volume 68| Part 1| January 2012| Page o24

doi:10.1107/S160053681105135X

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

Hui Wang,^a ^* Changlu Liu ^a and Feihua Luo ^a

^aDepartment of Chemistry and Chemical Engineering, Sichuan University of Arts and Science, Sichuan Key Laboratory of Characteristic Plant Development and Research, Sichuan Dazhou 635000, People's Republic of China
^*Correspondence e-mail: wjh686@163.com

(Received 29 October 2011; accepted 29 November 2011; online 3 December 2011)

The oxolan-2-one ring in the title compound, C₁₂H₉NO₄, 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_r = 231.20
Orthorhombic, P 2₁ 2₁ 2₁
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[F² > 2σ(F²)] = 0.028
wR(F²) = 0.073
S = 1.20
1077 reflections
154 parameters
H-atom parameters constrained
Δρ_max = 0.10 e Å⁻³
Δρ_min = −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).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053681105135X/lh5369sup1.cif

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

Supporting information file. DOI: 10.1107/S160053681105135X/lh5369Isup3.cml

checkCIF report

Comment top

The title compound is a key intermediate in our organic synthesis work. It was originally synthesized by Temperini et al. (2010). We report herein its crystal structure.

The molecular structure of the title compound (I) is shown in Fig. 1. The structure of the closely related compound, 2-(2,5-Dioxotetrahydrofuran-3-yl)isoindoline-1,3-dione, has already been published (Qian, 2008). In (I) The five-membered ring is in an envelope conformation.

Related literature top

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 top

The title compound was prepared from L-Aspartic acid as starting material. First, the amino acid was converted into the Cbz-protected lactone. Then, the Cbz-protected lactone (2.34 g, 10 mmoL) was hydrogenated at 1 atm with phthalic anhydride (1.78 g, 12 mmoL) in 30 mL of DMF and 0.53 g of 10% Pd/C. Single crystals suitable for X-ray diffraction were obtained by evaporation of the a DMF solution of the title compound.

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); 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).

Figures top

Fig. 1. The molecular structure of with displacement ellipsoids drawn at the 20% probability level.

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

Crystal data top

C₁₂H₉NO₄	F(000) = 480
M_r = 231.20	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0366P)² + 0.0827P] where P = (F_o² + 2F_c²)/3
1077 reflections	(Δ/σ)_max < 0.001
154 parameters	Δρ_max = 0.10 e Å⁻³
0 restraints	Δρ_min = −0.13 e Å⁻³

Crystal data top

C₁₂H₉NO₄	V = 1020.72 (9) Å³
M_r = 231.20	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 5.7224 (3) Å	µ = 0.12 mm⁻¹
b = 10.5839 (5) Å	T = 296 K
c = 16.8532 (10) Å	0.20 × 0.20 × 0.14 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	1077 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1002 reflections with I > 2σ(I)
T_min = 0.977, T_max = 0.984	R_int = 0.021
4468 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.028	0 restraints
wR(F²) = 0.073	H-atom parameters constrained
S = 1.20	Δρ_max = 0.10 e Å⁻³
1077 reflections	Δρ_min = −0.13 e Å⁻³
154 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Experimental details

Crystal data
Chemical formula	C₁₂H₉NO₄
M_r	231.20
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	296
a, b, c (Å)	5.7224 (3), 10.5839 (5), 16.8532 (10)
V (Å³)	1020.72 (9)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.12
Crystal size (mm)	0.20 × 0.20 × 0.14

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.977, 0.984
No. of measured, independent and observed [I > 2σ(I)] reflections	4468, 1077, 1002
R_int	0.021
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.028, 0.073, 1.20
No. of reflections	1077
No. of parameters	154
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.10, −0.13

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009), SHELXTL (Sheldrick, 2008).

Acknowledgements

This work was supported by the Scientific Research Foundation of Sichuan University of Arts and Science (No. 2010A05Z).

References

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