2,5-Dibromo-pyridine.

In the title compound, C(5)H(3)Br(2)N, C-H⋯N hydrogen-bonding inter-actions and Br⋯Br inter-actions [3.9418 (3) and 3.8986 (3) Å] connect the mol-ecules into planar sheets stacked perpendicular to the b axis. In addition, pyrid-yl-pyridyl inter-sheet π-π stacking inter-actions [centroid-centroid distance = 4.12 (1) Å] result in a three-dimensional network.

Related literature

For hydrogen bonding, see: Desiraju (1997 ▶). For related structures, see: Al-Far & Ali (2007 ▶, 2008 ▶); Ali & Al-Far (2008 ▶); Ali et al. (2008a ▶,b ▶). For bond-length data, see: Allen et al. (1987 ▶). For theoretical analysis, see: Awwadi et al. (2006 ▶, 2007 ▶).

Experimental

Crystal data

C5H3Br2N

M = 236.90

Orthorhombic,

a = 6.1063 (4) Å

b = 6.5442 (4) Å

c = 15.8196 (9) Å

V = 632.17 (7) Å3

Z = 4

Mo Kα radiation

μ = 12.71 mm−1

T = 90 K

0.46 × 0.21 × 0.14 mm

Data collection

Bruker SMART APEX diffractometer

Absorption correction: numerical (SADABS; Bruker, 2004 ▶) T min = 0.053, T max = 0.170

8997 measured reflections

996 independent reflections

887 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.021

wR(F 2) = 0.054

S = 1.05

996 reflections

49 parameters

H-atom parameters constrained

Δρmax = 0.68 e Å−3

Δρmin = −0.77 e Å−3

Data collection: SMART (Bruker, 2006 ▶); cell refinement: SAINT-Plus (Bruker, 2006 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL (Sheldrick, 2008 ▶); molecular graphics: XP (Bruker, 2004 ▶) and SHELXTL; software used to prepare material for publication: XCIF (Bruker, 2004 ▶) and SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053680900974X/pv2146sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680900974X/pv2146Isup2.hkl

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

C5H3Br2N	F(000) = 440
Mr = 236.90	Dx = 2.489 Mg m−3
Orthorhombic, Pnma	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2n	Cell parameters from 5485 reflections
a = 6.1063 (4) Å	θ = 2.6–30.0°
b = 6.5442 (4) Å	µ = 12.71 mm−1
c = 15.8196 (9) Å	T = 90 K
V = 632.17 (7) Å3	Diamond, colourless
Z = 4	0.46 × 0.21 × 0.14 mm

Bruker SMART APEX diffractometer	996 independent reflections
Radiation source: fine-focus sealed tube	887 reflections with I > 2σ(I)
graphite	Rint = 0.030
Detector resolution: 8.3 pixels mm-1	θmax = 30.0°, θmin = 3.6°
ω scans	h = −8→8
Absorption correction: numerical (SADABS; Bruker, 2004)	k = −9→9
Tmin = 0.053, Tmax = 0.170	l = −22→22
8997 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)] = 0.021	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.054	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0364P)2 + 0.1337P] where P = (Fo2 + 2Fc2)/3
996 reflections	(Δ/σ)max < 0.001
49 parameters	Δρmax = 0.68 e Å−3
0 restraints	Δρmin = −0.77 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
Br2	0.41023 (4)	0.7500	0.171199 (12)	0.01101 (9)
N1	0.4781 (3)	0.7500	−0.00105 (12)	0.0077 (4)
Br5	0.98268 (4)	0.7500	−0.173378 (13)	0.01214 (9)
C2	0.5860 (4)	0.7500	0.07141 (12)	0.0063 (4)
C3	0.8124 (3)	0.7500	0.07962 (13)	0.0089 (4)
H3A	0.8808	0.7500	0.1336	0.011*
C4	0.9342 (4)	0.7500	0.00590 (14)	0.0088 (4)
H4A	1.0897	0.7500	0.0077	0.011*
C5	0.8236 (4)	0.7500	−0.07079 (12)	0.0074 (4)
C6	0.5958 (4)	0.7500	−0.07196 (12)	0.0083 (4)
H6A	0.5221	0.7500	−0.1248	0.010*

	U11	U22	U33	U12	U13	U23
Br2	0.01285 (15)	0.01709 (15)	0.00310 (12)	0.000	0.00345 (7)	0.000
N1	0.0081 (9)	0.0110 (9)	0.0041 (8)	0.000	0.0000 (6)	0.000
Br5	0.01335 (15)	0.01839 (15)	0.00466 (13)	0.000	0.00480 (7)	0.000
C2	0.0095 (11)	0.0078 (10)	0.0015 (8)	0.000	0.0012 (7)	0.000
C3	0.0087 (10)	0.0114 (10)	0.0066 (9)	0.000	−0.0024 (8)	0.000
C4	0.0067 (9)	0.0114 (10)	0.0084 (10)	0.000	−0.0018 (8)	0.000
C5	0.0088 (10)	0.0096 (10)	0.0040 (9)	0.000	0.0026 (7)	0.000
C6	0.0100 (11)	0.0100 (11)	0.0048 (9)	0.000	−0.0019 (7)	0.000

Br2—C2	1.909 (2)	C3—H3A	0.9500
N1—C2	1.322 (3)	C4—C5	1.389 (3)
N1—C6	1.332 (3)	C4—H4A	0.9500
Br5—C5	1.891 (2)	C5—C6	1.391 (3)
C2—C3	1.389 (3)	C6—H6A	0.9500
C3—C4	1.383 (3)
C2—N1—C6	117.43 (19)	C3—C4—H4A	120.8
N1—C2—C3	125.27 (19)	C5—C4—H4A	120.8
N1—C2—Br2	115.88 (16)	C4—C5—C6	119.87 (19)
C3—C2—Br2	118.85 (15)	C4—C5—Br5	119.98 (17)
C4—C3—C2	117.15 (19)	C6—C5—Br5	120.15 (16)
C4—C3—H3A	121.4	N1—C6—C5	121.91 (19)
C2—C3—H3A	121.4	N1—C6—H6A	119.0
C3—C4—C5	118.38 (19)	C5—C6—H6A	119.0
C6—N1—C2—C3	0.0	C3—C4—C5—C6	0.0
C6—N1—C2—Br2	180.0	C3—C4—C5—Br5	180.0
N1—C2—C3—C4	0.0	C2—N1—C6—C5	0.0
Br2—C2—C3—C4	180.0	C4—C5—C6—N1	0.0
C2—C3—C4—C5	0.0	Br5—C5—C6—N1	180.0

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4A···N1i	0.95	2.38	3.323 (3)	175

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4A⋯N1i	0.95	2.38	3.323 (3)	175

Symmetry code: (i) .