1-(3-Pyrid­yl)pyrrolidine-2,5-dione

Hou, H.-B.; Liu, Y.-M.; Yang, L.-F.

doi:10.1107/S1600536809046522

organic compounds

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ISSN: 2056-9890

Volume 65| Part 12| December 2009| Page o3054

doi:10.1107/S1600536809046522

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1-(3-Pyridyl)pyrrolidine-2,5-dione

Hong-Bo Hou,^a ^* Yi-Ming Liu ^a and Luan-Fang Yang ^a

^aDepartment of Biology and Chemistry, Bao Shan College, BaoShan, Yun nan 678000, People's Republic of China.
^*Correspondence e-mail: hhb826@163.com

(Received 22 September 2009; accepted 4 November 2009; online 11 November 2009)

In the title molecule, C₉H₈N₂O₂, the dihedral angle between the pyridine and the pyrrolidine rings is 64.58 (12)°. In the crystal structure, weak C—H⋯π-electron ring interactions 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_r = 176.17
Orthorhombic, P n a 2₁
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[F² > 2σ(F²)] = 0.033
wR(F²) = 0.069
S = 1.00
852 reflections
119 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.11 e Å⁻³
Δρ_min = −0.10 e Å⁻³

Table 1
Hydrogen-bond geometry (Å)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8B⋯Cgⁱ	0.97	2.78	3.742 (6)	172
Symmetry code: (i) $[-x+1, -y+2, z+{\script{1\over 2}}]$ . Cg is the centroid of the N1,C1–C5 ring.

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 ).

Supporting information

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

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

checkCIF report

Comment top

The derivatives of pyrrolidine-2,5-dione possess valuable pharmaceutical properties (Obniska et al., 2009), among others are inhibitors of the cholesterol biosynthesis (Procopiou et al., 1993). These interesting properties lead us to develop pyrrolidine derivatives containing the pyrrolidine-2,5-dione and the pyridine groups. In this paper, the synthesis of one of these compounds and its crystal structure are reported.

In the title molecule (Fig. 1), the dihedral angle between the pyridine and the pyrrolidine rings equals to 64.58 (12)°, There are C—H···π-electron ring interactions between the hydrogen atom H8B stemming from the pyrrolidine ring and the pyridine ring that serves as an acceptor (Tab. 1).

Related literature top

For general background to the pharmaceutical properties of pyrrolidine-2,5-dione derivatives, see: Procopiou et al. (1993); Obniska et al. (2009). Cg is the centroid of the N1,C1–C5 ring .

Experimental top

Solution of pyrrolidine-2,5-dione (0.04 mol) in ethanol (96%, 15 ml) was added to a stirred ethanol solution (96%, 25 ml) of 3-chloropyridine (0.04 mol) at room temperature, then KOH (0.01 mol) and tetrabutylammonium bromide (0.005 mol) was added to the resulting solution. This mixture was heated at 323 K for 4 h and then cooled to room temperature. After 30 ml of water had been added to this mixture, a white precipitate appeared. The mixture was filtered, the residue was dried under a reduced pressure in a vacuum drying box for 3 hours, then the residue was dissolved in 100 ml of ethanol (96%), and set aside for five days to obtain colourless block crystals suitable for X-ray analysis. Yield: 43%.

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT (Bruker, 2002); 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).

Figures top

Fig. 1. The title molecule with the atom-labelling scheme. The displacement ellipsoids are drawn at the 50% probability level.

1-(3-Pyridyl)pyrrolidine-2,5-dione top

Crystal data top

C₉H₈N₂O₂	F(000) = 368
M_r = 176.17	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0287P)²] where P = (F_o² + 2F_c²)/3
S = 1.00	(Δ/σ)_max < 0.001
852 reflections	Δρ_max = 0.11 e Å⁻³
119 parameters	Δρ_min = −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

Crystal data top

C₉H₈N₂O₂	V = 898.6 (9) Å³
M_r = 176.17	Z = 4
Orthorhombic, Pna2₁	Mo Kα radiation
a = 12.137 (8) Å	µ = 0.10 mm⁻¹
b = 10.838 (6) Å	T = 293 K
c = 6.831 (4) Å	0.25 × 0.21 × 0.17 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	852 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	672 reflections with I > 2σ(I)
T_min = 0.977, T_max = 0.984	R_int = 0.073
3927 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.033	1 restraint
wR(F²) = 0.069	H-atom parameters constrained
S = 1.00	Δρ_max = 0.11 e Å⁻³
852 reflections	Δρ_min = −0.10 e Å⁻³
119 parameters

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq
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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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

Symmetry code: (i) −x+1, −y+2, z+1/2.

Experimental details

Crystal data
Chemical formula	C₉H₈N₂O₂
M_r	176.17
Crystal system, space group	Orthorhombic, Pna2₁
Temperature (K)	293
a, b, c (Å)	12.137 (8), 10.838 (6), 6.831 (4)
V (Å³)	898.6 (9)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.25 × 0.21 × 0.17

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.977, 0.984
No. of measured, independent and observed [I > 2σ(I)] reflections	3927, 852, 672
R_int	0.073
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.033, 0.069, 1.00
No. of reflections	852
No. of parameters	119
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.11, −0.10

Computer programs: SMART (Bruker, 2002), SAINT (Bruker, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8B···Cgⁱ	0.9700	2.7786	3.742 (6)	172

Symmetry code: (i) −x+1, −y+2, z+1/2.

Acknowledgements

The authors gratefully acknowledge the Natural Science Foundation of Bao Shan College (No. 09B004K) for financial support.

References

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