1-(3-Pyrid-yl)pyrrolidine-2,5-dione.

In the title mol-ecule, C(9)H(8)N(2)O(2), the dihedral angle between the pyridine and the pyrrolidine rings is 64.58 (12)°. In the crystal structure, weak C-H⋯π-electron ring inter-actions stabilize the packing.

Related literature

For general background to the pharmaceutical properties of pyrrolidine-2,5-dione derivatives, see: Procopiou et al. (1993 ▶); Obniska et al. (2009 ▶).

Experimental

Crystal data

C9H8N2O2

M = 176.17

Orthorhombic,

a = 12.137 (8) Å

b = 10.838 (6) Å

c = 6.831 (4) Å

V = 898.6 (9) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 293 K

0.25 × 0.21 × 0.17 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.977, T max = 0.984

3927 measured reflections

852 independent reflections

672 reflections with I > 2σ(I)

R int = 0.073

Refinement

R[F 2 > 2σ(F 2)] = 0.033

wR(F 2) = 0.069

S = 1.00

852 reflections

119 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.11 e Å−3

Δρmin = −0.10 e Å−3

Data collection: SMART (Bruker, 2002 ▶); cell refinement: SAINT (Bruker, 2002 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809046522/fb2172sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809046522/fb2172Isup2.hkl

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

C9H8N2O2	F(000) = 368
Mr = 176.17	Dx = 1.302 Mg m−3
Orthorhombic, Pna21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 852 reflections
a = 12.137 (8) Å	θ = 2.5–25.0°
b = 10.838 (6) Å	µ = 0.10 mm−1
c = 6.831 (4) Å	T = 293 K
V = 898.6 (9) Å3	Block, colourless
Z = 4	0.25 × 0.21 × 0.17 mm

Bruker SMART CCD area-detector diffractometer	852 independent reflections
Radiation source: fine-focus sealed tube	672 reflections with I > 2σ(I)
graphite	Rint = 0.073
φ and ω scans	θmax = 25.0°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −13→14
Tmin = 0.977, Tmax = 0.984	k = −12→12
3927 measured reflections	l = −8→7

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.033	H-atom parameters constrained
wR(F2) = 0.069	w = 1/[σ2(Fo2) + (0.0287P)2] where P = (Fo2 + 2Fc2)/3
S = 1.00	(Δ/σ)max < 0.001
852 reflections	Δρmax = 0.11 e Å−3
119 parameters	Δρmin = −0.10 e Å−3
1 restraint	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
32 constraints	Extinction coefficient: 0.128 (8)
Primary atom site location: structure-invariant direct methods

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
C1	0.46710 (19)	0.76727 (18)	0.7705 (4)	0.0421 (6)
C2	0.5641 (2)	0.7232 (2)	0.8551 (4)	0.0576 (8)
H2	0.5847	0.7545	0.9764	0.069*
C3	0.5975 (2)	0.5948 (2)	0.5932 (5)	0.0653 (9)
H3	0.6408	0.5352	0.5327	0.078*
C4	0.5034 (2)	0.6353 (2)	0.4968 (4)	0.0661 (8)
H4	0.4853	0.6040	0.3742	0.079*
C5	0.4364 (2)	0.7235 (2)	0.5857 (5)	0.0563 (8)
H5	0.3731	0.7523	0.5240	0.068*
C6	0.34810 (18)	0.8409 (2)	1.0491 (4)	0.0508 (7)
C7	0.29704 (19)	0.9616 (2)	1.1138 (4)	0.0578 (8)
H7A	0.3299	0.9897	1.2353	0.069*
H7B	0.2183	0.9524	1.1328	0.069*
C8	0.3213 (2)	1.0532 (2)	0.9462 (5)	0.0565 (8)
H8A	0.2534	1.0823	0.8874	0.068*
H8B	0.3625	1.1237	0.9943	0.068*
C9	0.38857 (18)	0.9809 (2)	0.8001 (5)	0.0505 (7)
N1	0.62967 (18)	0.63755 (19)	0.7709 (4)	0.0668 (7)
N2	0.40243 (14)	0.86060 (15)	0.8703 (3)	0.0417 (5)
O1	0.34353 (16)	0.74092 (18)	1.1328 (4)	0.0784 (7)
O2	0.42619 (16)	1.01652 (17)	0.6419 (4)	0.0797 (7)

	U11	U22	U33	U12	U13	U23
C1	0.0410 (13)	0.0403 (13)	0.0449 (17)	−0.0047 (10)	−0.0005 (13)	0.0029 (13)
C2	0.0566 (15)	0.0605 (16)	0.056 (2)	0.0107 (12)	−0.0101 (15)	−0.0018 (14)
C3	0.0721 (19)	0.0532 (16)	0.071 (2)	0.0082 (12)	0.0108 (19)	−0.0073 (16)
C4	0.0749 (18)	0.0639 (17)	0.060 (2)	−0.0014 (15)	−0.0085 (17)	−0.0176 (14)
C5	0.0496 (15)	0.0607 (17)	0.059 (2)	−0.0035 (12)	−0.0103 (14)	−0.0036 (15)
C6	0.0493 (14)	0.0581 (16)	0.0450 (19)	−0.0032 (13)	−0.0024 (13)	0.0052 (15)
C7	0.0484 (13)	0.0743 (17)	0.051 (2)	−0.0007 (13)	0.0042 (16)	−0.0066 (15)
C8	0.0445 (14)	0.0513 (15)	0.074 (2)	0.0018 (12)	0.0013 (14)	−0.0083 (16)
C9	0.0395 (12)	0.0501 (15)	0.062 (2)	−0.0033 (10)	0.0001 (14)	0.0065 (15)
N1	0.0668 (15)	0.0652 (15)	0.0684 (19)	0.0207 (11)	−0.0052 (15)	−0.0076 (15)
N2	0.0380 (10)	0.0427 (12)	0.0445 (14)	−0.0003 (8)	−0.0008 (10)	0.0044 (10)
O1	0.0992 (15)	0.0735 (13)	0.0624 (15)	0.0008 (11)	0.0115 (14)	0.0195 (11)
O2	0.0846 (13)	0.0681 (13)	0.0864 (17)	0.0147 (10)	0.0343 (13)	0.0302 (13)

C1—C2	1.396 (4)	C6—O1	1.226 (3)
C1—C5	1.399 (4)	C6—N2	1.404 (3)
C1—N2	1.450 (3)	C6—C7	1.514 (4)
C2—N1	1.351 (3)	C7—C8	1.544 (4)
C2—H2	0.9300	C7—H7A	0.9700
C3—N1	1.356 (4)	C7—H7B	0.9700
C3—C4	1.390 (4)	C8—C9	1.509 (4)
C3—H3	0.9300	C8—H8A	0.9700
C4—C5	1.393 (4)	C8—H8B	0.9700
C4—H4	0.9300	C9—O2	1.235 (4)
C5—H5	0.9300	C9—N2	1.400 (3)
C2—C1—C5	118.8 (2)	C6—C7—H7A	110.7
C2—C1—N2	120.0 (3)	C8—C7—H7A	110.7
C5—C1—N2	121.1 (2)	C6—C7—H7B	110.7
N1—C2—C1	123.8 (3)	C8—C7—H7B	110.7
N1—C2—H2	118.1	H7A—C7—H7B	108.8
C1—C2—H2	118.1	C9—C8—C7	105.1 (2)
N1—C3—C4	123.6 (3)	C9—C8—H8A	110.7
N1—C3—H3	118.2	C7—C8—H8A	110.7
C4—C3—H3	118.2	C9—C8—H8B	110.7
C3—C4—C5	119.3 (3)	C7—C8—H8B	110.7
C3—C4—H4	120.4	H8A—C8—H8B	108.8
C5—C4—H4	120.4	O2—C9—N2	123.1 (2)
C4—C5—C1	118.1 (3)	O2—C9—C8	128.1 (2)
C4—C5—H5	121.0	N2—C9—C8	108.8 (3)
C1—C5—H5	121.0	C2—N1—C3	116.5 (2)
O1—C6—N2	124.2 (2)	C9—N2—C6	112.6 (2)
O1—C6—C7	127.5 (3)	C9—N2—C1	123.6 (2)
N2—C6—C7	108.3 (2)	C6—N2—C1	123.8 (2)
C6—C7—C8	105.1 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8B···Cgi	0.97	2.78	3.742 (6)	172

Table 1

Hydrogen-bond geometry (Å)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8B⋯Cg i	0.97	2.78	3.742 (6)	172

Symmetry code: (i) . Cg is the centroid of the N1,C1–C5 ring.