4-Cyano-pyridinium bromide.

In the title compound, C(6)H(5)N(2) (+)·Br(-), the pyridine N atom is protonated and involved in an inter-molecular N-H⋯Br hydrogen bond which, together with weak C-H⋯N hydrogen bonds, results in the formation of a chain along the c axis. Weak inter-molecular C-H⋯Br inter-actions between pyridine H atoms and Br(-) anions connect these chains into a network parallel to the bc plane.

Related literature

For the structures and properties of related compounds see: Fu et al. (2011a ▶,b ▶); Dai & Chen (2011 ▶).

Experimental

Crystal data

C6H5N2 +·Br−

M = 185.03

Monoclinic,

a = 7.3918 (5) Å

b = 12.2587 (4) Å

c = 8.1671 (3) Å

β = 111.720 (1)°

V = 687.51 (6) Å3

Z = 4

Mo Kα radiation

μ = 5.88 mm−1

T = 173 K

0.10 × 0.05 × 0.05 mm

Data collection

Rigaku Mercury2 diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T min = 0.910, T max = 1.000

4771 measured reflections

1579 independent reflections

1296 reflections with I > 2σ(I)

R int = 0.047

Refinement

R[F 2 > 2σ(F 2)] = 0.032

wR(F 2) = 0.066

S = 0.95

1579 reflections

82 parameters

H-atom parameters constrained

Δρmax = 0.57 e Å−3

Δρmin = −0.92 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 datablock(s) I, global. DOI: 10.1107/S160053681202209X/mw2067sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681202209X/mw2067Isup2.hkl

Supplementary material file. DOI: 10.1107/S160053681202209X/mw2067Isup3.cml

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

C6H5N2+·Br−	F(000) = 360
Mr = 185.03	Dx = 1.788 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1579 reflections
a = 7.3918 (5) Å	θ = 3.2–27.5°
b = 12.2587 (4) Å	µ = 5.88 mm−1
c = 8.1671 (3) Å	T = 173 K
β = 111.720 (1)°	Block, colorless
V = 687.51 (6) Å3	0.10 × 0.05 × 0.05 mm
Z = 4

Rigaku Mercury2 diffractometer	1579 independent reflections
Radiation source: fine-focus sealed tube	1296 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.047
Detector resolution: 13.6612 pixels mm-1	θmax = 27.5°, θmin = 3.2°
ω & φ scans	h = −9→9
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −15→15
Tmin = 0.910, Tmax = 1.000	l = −10→10
4771 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)] = 0.032	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.066	H-atom parameters constrained
S = 0.95	w = 1/[σ2(Fo2) + (0.0255P)2] where P = (Fo2 + 2Fc2)/3
1579 reflections	(Δ/σ)max = 0.001
82 parameters	Δρmax = 0.57 e Å−3
0 restraints	Δρmin = −0.92 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
Br1	0.61085 (4)	0.41149 (2)	0.32517 (4)	0.01972 (12)
N1	0.4087 (4)	0.74050 (19)	−0.0107 (3)	0.0178 (6)
H1	0.4160	0.7079	−0.1068	0.021*
C1	0.4249 (4)	0.6702 (3)	0.1191 (4)	0.0218 (7)
H1A	0.4410	0.5962	0.1038	0.026*
C2	0.4176 (5)	0.7076 (2)	0.2761 (4)	0.0206 (7)
H2A	0.4295	0.6597	0.3677	0.025*
N2	0.3889 (4)	0.8933 (2)	0.5892 (4)	0.0318 (7)
C3	0.3922 (4)	0.8184 (2)	0.2937 (4)	0.0164 (7)
C4	0.3754 (4)	0.8896 (2)	0.1569 (4)	0.0198 (7)
H4A	0.3575	0.9640	0.1682	0.024*
C5	0.3857 (4)	0.8479 (2)	0.0032 (4)	0.0193 (7)
H5A	0.3767	0.8941	−0.0898	0.023*
C6	0.3875 (5)	0.8612 (3)	0.4580 (4)	0.0202 (7)

	U11	U22	U33	U12	U13	U23
Br1	0.0246 (2)	0.01924 (19)	0.01933 (18)	−0.00107 (15)	0.01284 (14)	−0.00215 (13)
N1	0.0149 (14)	0.0239 (14)	0.0174 (12)	0.0034 (11)	0.0094 (11)	−0.0039 (11)
C1	0.024 (2)	0.0189 (17)	0.0243 (17)	0.0035 (14)	0.0111 (15)	−0.0006 (14)
C2	0.0201 (18)	0.0237 (17)	0.0206 (16)	0.0045 (14)	0.0106 (14)	0.0037 (14)
N2	0.045 (2)	0.0311 (17)	0.0251 (15)	−0.0001 (15)	0.0200 (14)	−0.0045 (13)
C3	0.0082 (16)	0.0260 (17)	0.0163 (15)	0.0014 (13)	0.0060 (13)	0.0006 (13)
C4	0.0194 (18)	0.0212 (17)	0.0221 (16)	0.0005 (14)	0.0118 (14)	−0.0032 (13)
C5	0.0166 (18)	0.0226 (17)	0.0207 (16)	0.0007 (14)	0.0094 (14)	0.0034 (14)
C6	0.0184 (18)	0.0248 (17)	0.0194 (16)	−0.0007 (14)	0.0093 (14)	0.0022 (14)

N1—C1	1.337 (4)	N2—C6	1.138 (4)
N1—C5	1.337 (4)	C3—C4	1.387 (4)
N1—H1	0.9003	C3—C6	1.453 (4)
C1—C2	1.381 (4)	C4—C5	1.384 (4)
C1—H1A	0.9300	C4—H4A	0.9300
C2—C3	1.385 (4)	C5—H5A	0.9300
C2—H2A	0.9300
C1—N1—C5	122.9 (2)	C2—C3—C6	120.0 (3)
C1—N1—H1	112.9	C4—C3—C6	119.4 (3)
C5—N1—H1	124.2	C5—C4—C3	118.6 (3)
N1—C1—C2	120.0 (3)	C5—C4—H4A	120.7
N1—C1—H1A	120.0	C3—C4—H4A	120.7
C2—C1—H1A	120.0	N1—C5—C4	119.5 (3)
C1—C2—C3	118.4 (3)	N1—C5—H5A	120.2
C1—C2—H2A	120.8	C4—C5—H5A	120.2
C3—C2—H2A	120.8	N2—C6—C3	178.0 (4)
C2—C3—C4	120.6 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···Br1i	0.90	2.26	3.133 (2)	164
C1—H1A···Br1	0.93	2.88	3.615 (2)	137
C2—H2A···Br1ii	0.93	2.77	3.645 (2)	156
C5—H5A···N2iii	0.93	2.66	3.435 (4)	142

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯Br1i	0.90	2.26	3.133 (2)	164
C1—H1A⋯Br1	0.93	2.88	3.615 (2)	137
C2—H2A⋯Br1ii	0.93	2.77	3.645 (2)	156
C5—H5A⋯N2iii	0.93	2.66	3.435 (4)	142

Symmetry codes: (i) ; (ii) ; (iii) .