Pyrrolidine-2,5-dione.

In the title compound, C(4)H(5)NO(2), the non-H atoms are nearly coplanar, with a maximum deviation of 0.030 (1) Å. In the crystal, pairs of mol-ecules are linked by N-H⋯O hydrogen bonds into inversion dimers.

Related literature

For the synthesis, see: Ilieva et al. (2012 ▶); Adib et al. (2010 ▶). For the bioactivity of pyrrolidine-2,5-dione derivatives, see: Obniska et al. (2012 ▶); Ha et al. (2011 ▶); Kaminski et al. (2011 ▶). For related structures, see: Khorasani & Fernandes (2012 ▶); Mayes et al. (2008 ▶).

Experimental

Crystal data

C4H5NO2

M = 99.09

Orthorhombic,

a = 7.3661 (4) Å

b = 9.5504 (5) Å

c = 12.8501 (7) Å

V = 904.00 (8) Å3

Z = 8

Mo Kα radiation

μ = 0.12 mm−1

T = 135 K

0.40 × 0.35 × 0.30 mm

Data collection

Agilent Xcalibur Eos diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010 ▶) T min = 0.911, T max = 1.000

2022 measured reflections

915 independent reflections

732 reflections with I > 2σ(I)

R int = 0.018

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.097

S = 1.05

915 reflections

64 parameters

H-atom parameters constrained

Δρmax = 0.15 e Å−3

Δρmin = −0.29 e Å−3

Data collection: CrysAlis PRO (Agilent, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: OLEX2 (Dolomanov et al., 2009 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812035672/xu5605sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812035672/xu5605Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812035672/xu5605Isup3.cml

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

C4H5NO2	F(000) = 416
Mr = 99.09	Dx = 1.456 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.7107 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 806 reflections
a = 7.3661 (4) Å	θ = 3.2–28.9°
b = 9.5504 (5) Å	µ = 0.12 mm−1
c = 12.8501 (7) Å	T = 135 K
V = 904.00 (8) Å3	Block, colourless
Z = 8	0.40 × 0.35 × 0.30 mm

Agilent Xcalibur Eos diffractometer	915 independent reflections
Radiation source: Enhance (Mo) X-ray Source	732 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.018
Detector resolution: 16.0874 pixels mm-1	θmax = 26.4°, θmin = 3.2°
ω scans	h = −8→9
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	k = −11→6
Tmin = 0.911, Tmax = 1.000	l = −16→14
2022 measured reflections

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.097	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0457P)2 + 0.1774P] where P = (Fo2 + 2Fc2)/3
915 reflections	(Δ/σ)max < 0.001
64 parameters	Δρmax = 0.15 e Å−3
0 restraints	Δρmin = −0.29 e Å−3

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
N1	0.04477 (16)	0.61457 (13)	0.39506 (9)	0.0197 (3)
H1	0.0772	0.5317	0.4135	0.024*
O1	0.19664 (16)	0.61963 (11)	0.23948 (8)	0.0291 (3)
O2	−0.13630 (16)	0.66055 (12)	0.53572 (8)	0.0312 (3)
C2	0.0226 (2)	0.82282 (15)	0.30007 (12)	0.0211 (4)
H2A	−0.0546	0.8346	0.2395	0.025*
H2B	0.1184	0.8924	0.2979	0.025*
C1	0.10102 (19)	0.67648 (15)	0.30357 (12)	0.0197 (4)
C4	−0.0668 (2)	0.69665 (16)	0.45340 (11)	0.0204 (4)
C3	−0.0874 (2)	0.83593 (16)	0.40006 (11)	0.0230 (4)
H3A	−0.0403	0.9108	0.4434	0.028*
H3B	−0.2139	0.8549	0.3847	0.028*

	U11	U22	U33	U12	U13	U23
N1	0.0206 (6)	0.0160 (6)	0.0226 (7)	0.0026 (5)	−0.0004 (5)	0.0014 (5)
O1	0.0309 (6)	0.0239 (6)	0.0325 (6)	−0.0004 (5)	0.0126 (5)	−0.0002 (5)
O2	0.0430 (7)	0.0274 (6)	0.0232 (6)	0.0118 (6)	0.0087 (6)	0.0049 (5)
C2	0.0215 (7)	0.0171 (7)	0.0248 (8)	−0.0011 (6)	−0.0004 (6)	0.0020 (6)
C1	0.0173 (7)	0.0186 (8)	0.0231 (7)	−0.0044 (6)	0.0000 (6)	0.0002 (6)
C4	0.0221 (7)	0.0196 (7)	0.0194 (8)	0.0021 (6)	−0.0023 (6)	−0.0016 (6)
C3	0.0301 (8)	0.0167 (7)	0.0222 (8)	0.0015 (7)	0.0003 (7)	−0.0012 (6)

N1—H1	0.8600	C2—H2B	0.9700
N1—C1	1.3796 (19)	C2—C1	1.513 (2)
N1—C4	1.3609 (19)	C2—C3	1.524 (2)
O1—C1	1.2121 (17)	C4—C3	1.504 (2)
O2—C4	1.2246 (18)	C3—H3A	0.9700
C2—H2A	0.9700	C3—H3B	0.9700
C1—N1—H1	123.1	O1—C1—C2	127.99 (14)
C4—N1—H1	123.1	N1—C4—C3	108.61 (12)
C4—N1—C1	113.83 (13)	O2—C4—N1	124.48 (14)
H2A—C2—H2B	108.9	O2—C4—C3	126.91 (14)
C1—C2—H2A	110.8	C2—C3—H3A	110.8
C1—C2—H2B	110.8	C2—C3—H3B	110.8
C1—C2—C3	104.70 (12)	C4—C3—C2	104.96 (12)
C3—C2—H2A	110.8	C4—C3—H3A	110.8
C3—C2—H2B	110.8	C4—C3—H3B	110.8
N1—C1—C2	107.85 (12)	H3A—C3—H3B	108.8
O1—C1—N1	124.16 (14)
N1—C4—C3—C2	1.90 (16)	C4—N1—C1—O1	−177.92 (14)
O2—C4—C3—C2	−178.47 (14)	C4—N1—C1—C2	2.11 (16)
C1—N1—C4—O2	177.78 (14)	C3—C2—C1—N1	−0.75 (15)
C1—N1—C4—C3	−2.58 (17)	C3—C2—C1—O1	179.29 (15)
C1—C2—C3—C4	−0.66 (15)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2i	0.86	2.00	2.8548 (16)	176

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O2i	0.86	2.00	2.8548 (16)	176

Symmetry code: (i) .