3-Cyano-anilinium bromide.

In the cation of the title compound, C(7)H(7)N(2) (+)·Br(-), all non-H atoms are essentially coplanar [r.m.s. deviation = 0.010 (5) Å]. The compound is isomorphous with the chloride analogue. In the crystal, the cations and anions are connected by N-H⋯Br hydrogen bonds.

Related literature

For applications of metal-organic coordination compounds, see: Fu et al. (2007 ▶); Chen et al. (2001 ▶); Fu & Xiong (2008 ▶); Xiong et al. (1999 ▶); Xie et al. (2003 ▶); Zhao et al. (2004 ▶). For nitrile derivatives, see: Fu et al. (2008 ▶); Wang et al. 2002 ▶. For the chloride analogue, see: Wen (2008 ▶).

Experimental

Crystal data

C7H7N2 +·Br−

M = 199.06

Triclinic,

a = 4.6396 (9) Å

b = 6.1757 (12) Å

c = 13.542 (3) Å

α = 93.07 (3)°

β = 96.22 (3)°

γ = 97.33 (3)°

V = 381.68 (13) Å3

Z = 2

Mo Kα radiation

μ = 5.31 mm−1

T = 298 K

0.40 × 0.05 × 0.05 mm

Data collection

Rigaku Mercury2 diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T min = 0.90, T max = 1.00

3777 measured reflections

1716 independent reflections

1378 reflections with I > 2σ(I)

R int = 0.063

Refinement

R[F 2 > 2σ(F 2)] = 0.052

wR(F 2) = 0.134

S = 1.10

1716 reflections

92 parameters

H-atom parameters constrained

Δρmax = 0.71 e Å−3

Δρmin = −0.75 e Å−3

Data collection: CrystalClear (Rigaku, 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: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809034941/bx2236sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809034941/bx2236Isup2.hkl

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

C7H7N2+·Br−	Z = 2
Mr = 199.06	F(000) = 196
Triclinic, P1	Dx = 1.732 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 4.6396 (9) Å	Cell parameters from 1378 reflections
b = 6.1757 (12) Å	θ = 3.0–27.5°
c = 13.542 (3) Å	µ = 5.31 mm−1
α = 93.07 (3)°	T = 298 K
β = 96.22 (3)°	Block, colourless
γ = 97.33 (3)°	0.40 × 0.05 × 0.05 mm
V = 381.68 (13) Å3

Rigaku Mercury2 diffractometer	1716 independent reflections
Radiation source: fine-focus sealed tube	1378 reflections with I > 2σ(I)
graphite	Rint = 0.063
Detector resolution: 13.6612 pixels mm-1	θmax = 27.5°, θmin = 3.0°
CCD profile fitting scans	h = −6→5
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −8→8
Tmin = 0.90, Tmax = 1.00	l = −17→17
3777 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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.134	H-atom parameters constrained
S = 1.10	w = 1/[σ2(Fo2) + (0.053P)2 + 0.0394P] where P = (Fo2 + 2Fc2)/3
1716 reflections	(Δ/σ)max < 0.001
92 parameters	Δρmax = 0.71 e Å−3
0 restraints	Δρmin = −0.75 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
N2	0.6256 (9)	0.2461 (6)	0.6051 (3)	0.0419 (10)
H2A	0.7437	0.1446	0.5990	0.063*
H2B	0.7175	0.3755	0.5927	0.063*
H2C	0.4653	0.2118	0.5619	0.063*
N1	−0.0113 (11)	0.7158 (8)	0.8871 (4)	0.0575 (13)
C4	0.5438 (10)	0.2565 (7)	0.7064 (4)	0.0339 (10)
C3	0.3783 (10)	0.4177 (7)	0.7330 (3)	0.0349 (10)
H3	0.3215	0.5166	0.6877	0.042*
C2	0.3001 (10)	0.4273 (7)	0.8286 (4)	0.0350 (10)
C5	0.6331 (11)	0.1113 (7)	0.7719 (4)	0.0389 (11)
H5	0.7446	0.0048	0.7527	0.047*
C7	0.3878 (12)	0.2814 (8)	0.8962 (4)	0.0429 (12)
H7	0.3345	0.2889	0.9604	0.051*
C6	0.5540 (12)	0.1259 (8)	0.8677 (4)	0.0473 (13)
H6	0.6146	0.0287	0.9132	0.057*
C1	0.1216 (11)	0.5910 (8)	0.8593 (4)	0.0422 (12)
Br1	0.09268 (11)	0.23870 (7)	0.42210 (4)	0.0448 (2)

	U11	U22	U33	U12	U13	U23
N2	0.053 (3)	0.044 (2)	0.032 (2)	0.0176 (19)	0.0038 (19)	0.0003 (18)
N1	0.058 (3)	0.052 (3)	0.067 (3)	0.020 (2)	0.016 (3)	−0.004 (2)
C4	0.040 (3)	0.028 (2)	0.033 (3)	0.0073 (18)	0.004 (2)	−0.0017 (18)
C3	0.039 (3)	0.033 (2)	0.032 (3)	0.010 (2)	0.000 (2)	0.0010 (19)
C2	0.030 (2)	0.034 (2)	0.041 (3)	0.0057 (18)	0.005 (2)	−0.002 (2)
C5	0.049 (3)	0.034 (2)	0.037 (3)	0.018 (2)	0.007 (2)	−0.001 (2)
C7	0.056 (3)	0.039 (3)	0.035 (3)	0.011 (2)	0.010 (2)	0.000 (2)
C6	0.062 (4)	0.040 (3)	0.045 (3)	0.015 (2)	0.010 (3)	0.014 (2)
C1	0.045 (3)	0.040 (3)	0.044 (3)	0.012 (2)	0.011 (2)	0.000 (2)
Br1	0.0573 (4)	0.0399 (3)	0.0423 (4)	0.0214 (2)	0.0112 (3)	0.0037 (2)

N2—C4	1.463 (6)	C3—H3	0.9300
N2—H2A	0.8900	C2—C7	1.384 (7)
N2—H2B	0.8900	C2—C1	1.457 (6)
N2—H2C	0.8900	C5—C6	1.388 (7)
N1—C1	1.121 (6)	C5—H5	0.9300
C4—C5	1.365 (6)	C7—C6	1.371 (7)
C4—C3	1.388 (6)	C7—H7	0.9300
C3—C2	1.383 (7)	C6—H6	0.9300
C4—N2—H2A	109.5	C3—C2—C1	120.2 (4)
C4—N2—H2B	109.5	C7—C2—C1	119.1 (5)
H2A—N2—H2B	109.5	C4—C5—C6	118.6 (4)
C4—N2—H2C	109.5	C4—C5—H5	120.7
H2A—N2—H2C	109.5	C6—C5—H5	120.7
H2B—N2—H2C	109.5	C6—C7—C2	119.4 (5)
C5—C4—C3	122.0 (4)	C6—C7—H7	120.3
C5—C4—N2	119.8 (4)	C2—C7—H7	120.3
C3—C4—N2	118.2 (4)	C7—C6—C5	121.0 (5)
C2—C3—C4	118.2 (4)	C7—C6—H6	119.5
C2—C3—H3	120.9	C5—C6—H6	119.5
C4—C3—H3	120.9	N1—C1—C2	177.0 (6)
C3—C2—C7	120.7 (4)
C5—C4—C3—C2	−0.9 (7)	N2—C4—C5—C6	179.6 (5)
N2—C4—C3—C2	179.8 (4)	C3—C2—C7—C6	0.0 (7)
C4—C3—C2—C7	0.7 (7)	C1—C2—C7—C6	179.5 (5)
C4—C3—C2—C1	−178.8 (4)	C2—C7—C6—C5	−0.6 (8)
C3—C4—C5—C6	0.3 (7)	C4—C5—C6—C7	0.5 (8)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···Br1i	0.89	2.59	3.434 (4)	159
N2—H2B···Br1ii	0.89	2.46	3.337 (4)	169
N2—H2C···Br1	0.89	2.45	3.299 (4)	160

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯Br1i	0.89	2.59	3.434 (4)	159
N2—H2B⋯Br1ii	0.89	2.46	3.337 (4)	169
N2—H2C⋯Br1	0.89	2.45	3.299 (4)	160

Symmetry codes: (i) ; (ii) .