Pyrrolidine-2,5-dione

In the title compound, C₄H₅NO₂, the non-H atoms are nearly coplanar, with a maximum deviation of 0.030 (1) Å. In the crystal, pairs of mol­ecules 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_r = 99.09

• Orthorhombic, P b c a

• a = 7.3661 (4) Å

• b = 9.5504 (5) Å

• c = 12.8501 (7) Å

• V = 904.00 (8) ų

• 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[F² > 2σ(F²)] = 0.039

• wR(F²) = 0.097

• S = 1.05

• 915 reflections

• 64 parameters

• H-atom parameters constrained

• Δρ_max = 0.15 e Å⁻³

• Δρ_min = −0.29 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O2^i	0.86	2.00	2.8548 (16)	176
Symmetry code: (i) -x, -y+1, -z+1.

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).

Supporting information

S1. Comment

Pyrrolidine-2,5-diones derivates are an important class of heterocylic compounds with essential applications in the organic synthesis and medicinal chemistry. In the organic field, pyrrolidine-2,5-diones derivates, such as well known 1-bromopyrrolidine-2,5-dione (NBS), are the most commonly used halogenation reagents. Meanwhile, pyrrolidine-2,5-diones derivates exhibit numerous bioactivity, especially in anticonvulsant (Obniska et al., 2012; Kaminski et al., 2011) and tyrosinase inhibitory activity (Ha et al., 2011). Therefore, development of new and efficient strategies for the synthesis of multi-substituted pyrrolidine-2,5-diones is also the current hot in organic and medical chemistry (Ilieva et al., 2012; Adib et al.. 2010). Several crystal structures of title compound derivates have been reported (Khorasani and Fernandes 2012; Mayes et al., 2008), but crystal data of pyrrolidine-2,5-dione has not been investigated. Herein, we report the synthesis and completely crystal data of title compound.

The molecular structure of pyrrolidine-2,5-dione is shown in Fig. 1. The bond lengths and angles are within normal ranges. In the crystal, the molecules are connected through intermolecular N–H···O hydrogen bond (Table 1).

Related literature

For the sythesis, see: Ilieva et al. (2012); Adib et al. (2010). For the bioactiviy 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).

S2. Experimental

The single crystals of pyrrolidine-2,5-dione, C₄H₅NO₂, were recrystallized from acetone at room temperature to give the desired crystals suitable for single-crystal X-ray diffraction, mounted inert oil and transferred to the cold gas stream of the diffractometer

S3. Refinement

C and N bound-H (atoms were included in idealized positions and refined using a riding-model approximation, with C—H bond lengths fixed at 1.00 Å, 0.99 Å, for methine and methylene H atoms respectively. U_iso(H) values were fixed at 1.2Ueq of the parent atoms for all H atoms.

Computing details

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

Figures

Fig. 1. The title compound with displacement ellipsoids drawn at the 50% probability level. H atoms are shown as spheres of arbitary radius.

Fig. 2. Plane-to-plane stacking of alternate molecules parallel to the α axis.

Pyrrolidine-2,5-dione

Crystal data

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) Å^3	Block, colourless
Z = 8	0.40 × 0.35 × 0.30 mm

Data collection

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

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.097	H-atom parameters constrained
S = 1.05	w = 1/[σ^2(Fo^2) + (0.0457P)^2 + 0.1774P] where P = (Fo^2 + 2Fc^2)/3
915 reflections	(Δ/σ)max < 0.001
64 parameters	Δρmax = 0.15 e Å^−3
0 restraints	Δρmin = −0.29 e Å^−3

Special details

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 (Ų)

	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*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

Geometric parameters (Å, º)

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)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2^i	0.86	2.00	2.8548 (16)	176

Symmetry code: (i) −x, −y+1, −z+1.