3-Bromo-pyridin-2-amine.

In the crystal structure of the title compound, C(5)H(5)BrN(2), mol-ecules assemble via pairs of N-H⋯N hydrogen bonds into inversion dimers using only the syn H atom on the amine group. These dimers then assemble further into two-dimensional layers via type I C-Br⋯Br [Br⋯Br = 3.693 (s6) Å] halogen bonding along the (102) plane.

Related literature

For halogen bonding, see: Metrangelo et al. (2005 ▶). For a related structure, see: Hu et al. (2011 ▶).

Experimental

Crystal data

C5H5BrN2

M = 173.02

Monoclinic,

a = 12.2179 (6) Å

b = 4.0007 (2) Å

c = 12.8451 (6) Å

β = 109.731 (3)°

V = 591.01 (5) Å3

Z = 4

Mo Kα radiation

μ = 6.84 mm−1

T = 173 K

0.5 × 0.4 × 0.09 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: integration (XPREP; Bruker, 2004 ▶) T min = 0.131, T max = 0.578

5622 measured reflections

1428 independent reflections

1200 reflections with I > 2σ(I)

R int = 0.093

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.082

S = 0.99

1428 reflections

81 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 1.04 e Å−3

Δρmin = −0.77 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT-Plus (Bruker, 2004 ▶); data reduction: SAINT-Plus and XPREP (Bruker 2004 ▶); 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 ▶) and DIAMOND (Brandenburg, 1999 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811055541/zj2050sup1.cif

Supplementary material file. DOI: 10.1107/S1600536811055541/zj2050Isup2.mol

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811055541/zj2050Isup3.hkl

Supplementary material file. DOI: 10.1107/S1600536811055541/zj2050Isup4.cml

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

C5H5BrN2	F(000) = 336
Mr = 173.02	Dx = 1.945 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2888 reflections
a = 12.2179 (6) Å	θ = 3.2–28.3°
b = 4.0007 (2) Å	µ = 6.84 mm−1
c = 12.8451 (6) Å	T = 173 K
β = 109.731 (3)°	Plate, brown
V = 591.01 (5) Å3	0.5 × 0.4 × 0.09 mm
Z = 4

Bruker SMART APEXII CCD area-detector diffractometer	1200 reflections with I > 2σ(I)
ω scans	Rint = 0.093
Absorption correction: integration (XPREP; Bruker, 2004)	θmax = 28.0°, θmin = 1.8°
Tmin = 0.131, Tmax = 0.578	h = −16→15
5622 measured reflections	k = −5→5
1428 independent reflections	l = −16→16

Refinement on F2	0 restraints
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.034	w = 1/[σ2(Fo2) + (0.0479P)2] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.082	(Δ/σ)max < 0.001
S = 0.99	Δρmax = 1.04 e Å−3
1428 reflections	Δρmin = −0.77 e Å−3
81 parameters

Experimental. Numerical integration absorption corrections based on indexed crystal faces were applied using the XPREP routine (Bruker, 2004)

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.

	x	y	z	Uiso*/Ueq
C2	0.8182 (2)	0.4235 (7)	0.4926 (2)	0.0288 (6)
C3	0.7048 (2)	0.3668 (6)	0.4912 (2)	0.0267 (5)
C4	0.6702 (2)	0.4704 (7)	0.5771 (2)	0.0309 (6)
H4	0.5934	0.4287	0.5763	0.037*
C5	0.7499 (3)	0.6374 (7)	0.6653 (2)	0.0327 (6)
H5	0.729	0.7168	0.7258	0.039*
C6	0.8602 (3)	0.6833 (7)	0.6615 (2)	0.0334 (6)
H6	0.915	0.7976	0.7215	0.04*
N1	0.8956 (2)	0.5781 (6)	0.5793 (2)	0.0325 (5)
N2	0.8547 (3)	0.3359 (7)	0.4077 (2)	0.0386 (6)
Br1	0.59557 (2)	0.15619 (6)	0.36599 (2)	0.03201 (13)
H2S	0.923 (3)	0.345 (7)	0.415 (3)	0.030 (9)*
H2A	0.820 (4)	0.210 (8)	0.362 (4)	0.043 (11)*

	U11	U22	U33	U12	U13	U23
C2	0.0309 (14)	0.0294 (12)	0.0253 (12)	0.0002 (11)	0.0084 (11)	0.0031 (10)
C3	0.0271 (14)	0.0256 (12)	0.0238 (12)	0.0031 (9)	0.0039 (11)	0.0034 (9)
C4	0.0282 (14)	0.0331 (13)	0.0319 (13)	0.0070 (11)	0.0107 (11)	0.0076 (12)
C5	0.0359 (16)	0.0376 (15)	0.0250 (13)	0.0059 (11)	0.0109 (12)	0.0036 (10)
C6	0.0343 (16)	0.0367 (15)	0.0273 (13)	−0.0010 (12)	0.0079 (12)	0.0002 (11)
N1	0.0286 (13)	0.0408 (12)	0.0266 (11)	−0.0041 (10)	0.0073 (10)	−0.0022 (10)
N2	0.0303 (15)	0.0568 (18)	0.0309 (13)	−0.0112 (12)	0.0134 (12)	−0.0120 (12)
Br1	0.02548 (18)	0.03463 (19)	0.03161 (18)	0.00029 (10)	0.00396 (12)	−0.00178 (10)

C2—N1	1.344 (4)	C5—C6	1.378 (5)
C2—N2	1.357 (4)	C5—H5	0.95
C2—C3	1.398 (4)	C6—N1	1.336 (4)
C3—C4	1.372 (4)	C6—H6	0.95
C3—Br1	1.904 (3)	N2—H2S	0.81 (4)
C4—C5	1.390 (4)	N2—H2A	0.78 (4)
C4—H4	0.95
N1—C2—N2	117.1 (3)	C6—C5—H5	121.3
N1—C2—C3	120.2 (2)	C4—C5—H5	121.3
N2—C2—C3	122.7 (3)	N1—C6—C5	124.6 (3)
C4—C3—C2	120.8 (3)	N1—C6—H6	117.7
C4—C3—Br1	119.7 (2)	C5—C6—H6	117.7
C2—C3—Br1	119.5 (2)	C6—N1—C2	118.4 (2)
C3—C4—C5	118.7 (3)	C2—N2—H2S	120 (3)
C3—C4—H4	120.6	C2—N2—H2A	122 (3)
C5—C4—H4	120.6	H2S—N2—H2A	113 (4)
C6—C5—C4	117.3 (3)
N1—C2—C3—C4	0.7 (4)	C3—C4—C5—C6	−1.1 (4)
N2—C2—C3—C4	−177.6 (3)	C4—C5—C6—N1	−0.1 (4)
N1—C2—C3—Br1	178.6 (2)	C5—C6—N1—C2	1.7 (4)
N2—C2—C3—Br1	0.3 (4)	N2—C2—N1—C6	176.5 (3)
C2—C3—C4—C5	0.9 (4)	C3—C2—N1—C6	−1.9 (4)
Br1—C3—C4—C5	−177.04 (19)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2S···N1i	0.81 (4)	2.21 (4)	3.019 (4)	173 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2S⋯N1i	0.81 (4)	2.21 (4)	3.019 (4)	173 (3)

Symmetry code: (i) .