2,3-Dichloro-pyridine.

The complete mol-ecule of the title compound, C(5)H(3)Cl(2)N, is generated by crystallographic twofold symmetry, which forces the pyridine N atom and the opposite C-H group to be statistically disordered. In the crystal, weak aromatic π-π stacking [centroid-centroid separation = 3.805 (4) Å and slippage = 1.704 Å] leads to [100] stacks of mol-ecules. Short Cl⋯Cl contacts [3.334 (3) Å] are also observed.

Related literature

For the biological activity of related compounds, see: Liu et al. (2011 ▶). For related structures, see: Ma et al. (2007 ▶), Liu & Liu (2011 ▶).

Experimental

Crystal data

C5H3Cl2N

M = 147.98

Monoclinic,

a = 3.805 (3) Å

b = 14.196 (12) Å

c = 10.68 (1) Å

β = 97.221 (14)°

V = 572.3 (9) Å3

Z = 4

Mo Kα radiation

μ = 1.00 mm−1

T = 113 K

0.36 × 0.04 × 0.04 mm

Data collection

Rigaku Saturn CCD diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005 ▶) T min = 0.714, T max = 0.961

2936 measured reflections

675 independent reflections

541 reflections with I > 2σ(I)

R int = 0.044

Refinement

R[F 2 > 2σ(F 2)] = 0.025

wR(F 2) = 0.054

S = 1.01

675 reflections

43 parameters

2 restraints

All H-atom parameters refined

Δρmax = 0.31 e Å−3

Δρmin = −0.19 e Å−3

Data collection: CrystalClear (Rigaku/MSC, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: CrystalStructure (Rigaku/MSC, 2005 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811030261/hb5953sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811030261/hb5953Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811030261/hb5953Isup3.cml

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

C5H3Cl2N	F(000) = 296
Mr = 147.98	Dx = 1.717 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 985 reflections
a = 3.805 (3) Å	θ = 1.9–27.8°
b = 14.196 (12) Å	µ = 1.00 mm−1
c = 10.68 (1) Å	T = 113 K
β = 97.221 (14)°	Prism, colorless
V = 572.3 (9) Å3	0.36 × 0.04 × 0.04 mm
Z = 4

Rigaku Saturn CCD diffractometer	675 independent reflections
Radiation source: rotating anode	541 reflections with I > 2σ(I)
multilayer	Rint = 0.044
Detector resolution: 14.63 pixels mm-1	θmax = 27.8°, θmin = 2.9°
ω and φ scans	h = −4→4
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)	k = −18→18
Tmin = 0.714, Tmax = 0.961	l = −13→13
2936 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)] = 0.025	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.054	All H-atom parameters refined
S = 1.01	w = 1/[σ2(Fo2) + (0.022P)2] where P = (Fo2 + 2Fc2)/3
675 reflections	(Δ/σ)max = 0.001
43 parameters	Δρmax = 0.31 e Å−3
2 restraints	Δρmin = −0.19 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	Occ. (<1)
Cl1	0.26918 (10)	0.32961 (3)	0.61537 (4)	0.02346 (14)
C1	0.3983 (4)	0.43421 (10)	0.69098 (13)	0.0154 (3)
C2	0.2951 (3)	0.51548 (10)	0.63275 (12)	0.0182 (3)	0.50
H2	0.138 (6)	0.514 (2)	0.5570 (16)	0.022*	0.50
N1	0.2951 (3)	0.51548 (10)	0.63275 (12)	0.0182 (3)	0.50
C3	0.3971 (4)	0.59762 (10)	0.69191 (15)	0.0214 (4)
H3	0.312 (4)	0.6559 (8)	0.6561 (15)	0.026*

	U11	U22	U33	U12	U13	U23
Cl1	0.0279 (3)	0.0201 (2)	0.0216 (2)	−0.00436 (16)	0.00026 (17)	−0.00631 (16)
C1	0.0142 (8)	0.0163 (7)	0.0160 (7)	−0.0009 (6)	0.0031 (6)	−0.0027 (6)
C2	0.0158 (8)	0.0235 (7)	0.0149 (7)	−0.0009 (6)	0.0008 (6)	0.0016 (6)
N1	0.0158 (8)	0.0235 (7)	0.0149 (7)	−0.0009 (6)	0.0008 (6)	0.0016 (6)
C3	0.0184 (9)	0.0185 (8)	0.0269 (9)	0.0015 (6)	0.0012 (7)	0.0073 (7)

Cl1—C1	1.7317 (18)	C2—H2	0.943 (10)
C1—C2	1.346 (2)	C3—C3i	1.382 (3)
C1—C1i	1.394 (3)	C3—H3	0.951 (9)
C2—C3	1.359 (2)
C2—C1—C1i	120.97 (9)	C3—C2—H2	122.4 (18)
C2—C1—Cl1	118.07 (12)	C2—C3—C3i	120.92 (9)
C1i—C1—Cl1	120.96 (6)	C2—C3—H3	119.8 (10)
C1—C2—C3	118.10 (14)	C3i—C3—H3	119.1 (10)
C1—C2—H2	119.2 (18)
C1i—C1—C2—C3	0.5 (3)	C1—C2—C3—C3i	0.5 (3)
Cl1—C1—C2—C3	−179.84 (12)