2-Cyano-anilinium bromide.

In the cation of the title compound, C(7)H(7)N(2) (+)·Br(-), the nitrile group and the benzene ring are almost coplanar (r.m.s. deviation = 0.0043 Å). In the crystal, the cations and anions are connected by inter-molecular N-H⋯Br hydrogen bonds, forming a two-dimensional network parallel to (010).

Related literature

For nitrile derivatives, see: Fu et al. (2008 ▶); Wang et al. (2002 ▶). Nitrile derivatives used in the construction of novel metal-organic frameworks. For applications of metal-organic coordination compounds, see: Fu et al. (2007 ▶); Chen et al. (2000 ▶); Fu & Xiong (2008 ▶); Xiong et al. (1999 ▶); Xie et al. (2003 ▶); Zhang et al. (2001 ▶).

Experimental

Crystal data

C7H7N2 +·Br−

M = 199.06

Monoclinic,

a = 5.7844 (12) Å

b = 15.896 (3) Å

c = 8.4882 (17) Å

β = 92.72 (3)°

V = 779.6 (3) Å3

Z = 4

Mo Kα radiation

μ = 5.19 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 = 0.65, T max = 0.77

3848 measured reflections

1773 independent reflections

1581 reflections with I > 2σ(I)

R int = 0.034

Refinement

R[F 2 > 2σ(F 2)] = 0.025

wR(F 2) = 0.050

S = 0.87

1773 reflections

93 parameters

2 restraints

H-atom parameters constrained

Δρmax = 0.47 e Å−3

Δρmin = −0.41 e Å−3

Absolute structure: Flack (1983 ▶), 872 Friedels pairs

Flack parameter: 0.004 (13)

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

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809035223/xu2593sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809035223/xu2593Isup2.hkl

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

C7H7N2+·Br−	F(000) = 392
Mr = 199.06	Dx = 1.696 Mg m−3
Monoclinic, Cc	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2yc	Cell parameters from 1581 reflections
a = 5.7844 (12) Å	θ = 2.6–27.5°
b = 15.896 (3) Å	µ = 5.19 mm−1
c = 8.4882 (17) Å	T = 298 K
β = 92.72 (3)°	Needle, colourless
V = 779.6 (3) Å3	0.40 × 0.05 × 0.05 mm
Z = 4

Rigaku Mercury2 diffractometer	1773 independent reflections
Radiation source: fine-focus sealed tube	1581 reflections with I > 2σ(I)
graphite	Rint = 0.034
Detector resolution: 13.6612 pixels mm-1	θmax = 27.5°, θmin = 2.6°
CCD profile fitting scans	h = −7→7
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −20→20
Tmin = 0.65, Tmax = 0.77	l = −10→11
3848 measured reflections

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.025	w = 1/[σ2(Fo2) + (0.0143P)2] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.050	(Δ/σ)max < 0.001
S = 0.87	Δρmax = 0.47 e Å−3
1773 reflections	Δρmin = −0.41 e Å−3
93 parameters	Extinction correction: SHELXTL (Version 5.1; Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
2 restraints	Extinction coefficient: 0.0206 (8)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), 872 Friedels pairs
Secondary atom site location: difference Fourier map	Flack parameter: 0.004 (13)

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
Br1	0.05750 (10)	0.208462 (17)	0.44566 (9)	0.04064 (12)
N1	0.0515 (5)	0.32177 (17)	0.7619 (3)	0.0347 (6)
H1A	0.0332	0.2950	0.6701	0.052*
H1B	−0.0713	0.3127	0.8188	0.052*
H1C	0.1780	0.3027	0.8140	0.052*
C6	−0.0799 (6)	0.4675 (3)	0.7945 (5)	0.0372 (10)
H6	−0.2028	0.4473	0.8503	0.045*
C3	0.2867 (8)	0.5276 (3)	0.6309 (5)	0.0451 (11)
H3	0.4102	0.5483	0.5762	0.054*
C1	0.0755 (6)	0.4115 (2)	0.7337 (5)	0.0309 (9)
C4	0.1322 (8)	0.5822 (3)	0.6917 (5)	0.0500 (12)
H4	0.1516	0.6399	0.6788	0.060*
C7	0.4233 (6)	0.3856 (2)	0.5783 (4)	0.0410 (8)
N2	0.5521 (6)	0.3440 (2)	0.5163 (4)	0.0618 (10)
C2	0.2611 (6)	0.4411 (3)	0.6501 (4)	0.0346 (9)
C5	−0.0547 (7)	0.5521 (3)	0.7733 (5)	0.0474 (12)
H5	−0.1613	0.5894	0.8130	0.057*

	U11	U22	U33	U12	U13	U23
Br1	0.03349 (17)	0.04202 (18)	0.04729 (19)	−0.0034 (2)	0.01111 (12)	−0.0112 (3)
N1	0.0284 (14)	0.0369 (15)	0.0396 (16)	−0.0027 (12)	0.0104 (12)	−0.0036 (13)
C6	0.031 (2)	0.043 (2)	0.038 (2)	−0.0023 (18)	0.0075 (17)	−0.0038 (18)
C3	0.044 (3)	0.046 (3)	0.046 (3)	−0.012 (2)	0.007 (2)	0.003 (2)
C1	0.027 (2)	0.035 (2)	0.0309 (18)	0.0005 (15)	0.0021 (15)	−0.0028 (15)
C4	0.065 (3)	0.031 (2)	0.055 (3)	−0.004 (2)	0.008 (2)	0.003 (2)
C7	0.0303 (18)	0.049 (2)	0.044 (2)	−0.0078 (17)	0.0101 (16)	0.0045 (18)
N2	0.049 (2)	0.070 (2)	0.069 (2)	0.0068 (19)	0.031 (2)	0.0025 (18)
C2	0.032 (2)	0.039 (2)	0.032 (2)	−0.0017 (17)	0.0039 (17)	0.0032 (16)
C5	0.056 (3)	0.041 (2)	0.045 (3)	0.012 (2)	0.006 (2)	−0.007 (2)

N1—C1	1.455 (5)	C3—C2	1.393 (6)
N1—H1A	0.8900	C3—H3	0.9300
N1—H1B	0.8900	C1—C2	1.396 (5)
N1—H1C	0.8900	C4—C5	1.396 (6)
C6—C5	1.366 (6)	C4—H4	0.9300
C6—C1	1.382 (5)	C7—N2	1.142 (4)
C6—H6	0.9300	C7—C2	1.444 (6)
C3—C4	1.365 (6)	C5—H5	0.9300
C1—N1—H1A	109.5	C6—C1—N1	120.1 (3)
C1—N1—H1B	109.5	C2—C1—N1	119.7 (3)
H1A—N1—H1B	109.5	C3—C4—C5	120.4 (4)
C1—N1—H1C	109.5	C3—C4—H4	119.8
H1A—N1—H1C	109.5	C5—C4—H4	119.8
H1B—N1—H1C	109.5	N2—C7—C2	177.0 (4)
C5—C6—C1	120.6 (4)	C3—C2—C1	118.7 (4)
C5—C6—H6	119.7	C3—C2—C7	118.6 (4)
C1—C6—H6	119.7	C1—C2—C7	122.6 (4)
C4—C3—C2	120.5 (4)	C6—C5—C4	119.5 (4)
C4—C3—H3	119.7	C6—C5—H5	120.2
C2—C3—H3	119.7	C4—C5—H5	120.2
C6—C1—C2	120.2 (4)
C5—C6—C1—C2	0.2 (6)	N1—C1—C2—C3	−177.0 (4)
C5—C6—C1—N1	177.8 (4)	C6—C1—C2—C7	−177.4 (4)
C2—C3—C4—C5	−0.4 (7)	N1—C1—C2—C7	5.0 (6)
C4—C3—C2—C1	−0.5 (6)	C1—C6—C5—C4	−1.1 (7)
C4—C3—C2—C7	177.6 (4)	C3—C4—C5—C6	1.2 (7)
C6—C1—C2—C3	0.6 (6)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···Br1	0.89	2.36	3.234 (3)	168
N1—H1B···Br1i	0.89	2.47	3.355 (3)	173
N1—H1C···Br1ii	0.89	2.42	3.286 (3)	164

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯Br1	0.89	2.36	3.234 (3)	168
N1—H1B⋯Br1i	0.89	2.47	3.355 (3)	173
N1—H1C⋯Br1ii	0.89	2.42	3.286 (3)	164

Symmetry codes: (i) ; (ii) .