4-Cyano-pyridinium chloride.

In the crystal structure of the title salt, C(6)H(5)N(2) (+)·Cl(-), the pyridinium cation links to the Cl(-) anion via an N-H⋯Cl hydrogen bond. Weak C-H⋯Cl inter-actions also occur.

Related literature

For the structures and properties of related compounds, see: Chen et al. (2000 ▶); Dai & Chen (2011 ▶); Xu et al. (2011 ▶); Liu et al. (1999 ▶); Zhao et al. (2003 ▶); Zheng (2011 ▶).

Experimental

Crystal data

C6H5N2 +·Cl−

M = 140.57

Triclinic,

a = 6.6166 (2) Å

b = 7.6552 (3) Å

c = 8.3495 (5) Å

α = 63.957 (5)°

β = 69.830 (2)°

γ = 74.367 (4)°

V = 353.16 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.45 mm−1

T = 123 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

3077 measured reflections

1231 independent reflections

1078 reflections with I > 2σ(I)

R int = 0.042

Refinement

R[F 2 > 2σ(F 2)] = 0.086

wR(F 2) = 0.234

S = 1.32

1231 reflections

82 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.97 e Å−3

Δρmin = −0.62 e Å−3

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 datablock(s) I, global. DOI: 10.1107/S1600536812018648/xu5524sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812018648/xu5524Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812018648/xu5524Isup3.cml

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

C6H5N2+·Cl−	Z = 2
Mr = 140.57	F(000) = 144
Triclinic, P1	Dx = 1.322 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.6166 (2) Å	Cell parameters from 1231 reflections
b = 7.6552 (3) Å	θ = 2.8–27.5°
c = 8.3495 (5) Å	µ = 0.45 mm−1
α = 63.957 (5)°	T = 123 K
β = 69.830 (2)°	Block, colorless
γ = 74.367 (4)°	0.10 × 0.05 × 0.05 mm
V = 353.16 (3) Å3

Rigaku Mercury2 diffractometer	1231 independent reflections
Radiation source: fine-focus sealed tube	1078 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.042
Detector resolution: 13.6612 pixels mm-1	θmax = 25.0°, θmin = 2.8°
CCD profile fitting scans	h = −7→7
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −9→9
Tmin = 0.910, Tmax = 1.000	l = −9→9
3077 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)] = 0.086	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.234	H-atom parameters constrained
S = 1.32	w = 1/[σ2(Fo2) + (0.0002P)2 + 3.2997P] where P = (Fo2 + 2Fc2)/3
1231 reflections	(Δ/σ)max < 0.001
82 parameters	Δρmax = 0.97 e Å−3
1 restraint	Δρmin = −0.62 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	0.8017 (7)	0.1582 (6)	0.6278 (6)	0.0267 (11)
N1	0.4202 (7)	0.2736 (6)	0.0960 (6)	0.0234 (10)
H1	0.3576	0.2900	0.0094	0.028*
C1	0.6318 (8)	0.1817 (7)	0.0856 (7)	0.0238 (12)
H1A	0.7092	0.1377	−0.0122	0.029*
C3	0.6118 (8)	0.2221 (7)	0.3646 (6)	0.0192 (11)
C4	0.3919 (8)	0.3182 (7)	0.3713 (7)	0.0238 (13)
H4A	0.3103	0.3648	0.4667	0.029*
C6	0.7156 (8)	0.1908 (7)	0.5071 (7)	0.0258 (13)
C5	0.3016 (8)	0.3411 (7)	0.2334 (7)	0.0251 (13)
H5A	0.1565	0.4042	0.2349	0.030*
C2	0.7328 (8)	0.1531 (7)	0.2198 (7)	0.0222 (12)
H2A	0.8783	0.0894	0.2146	0.027*
Cl1	0.1808 (2)	0.31778 (18)	0.82634 (17)	0.0249 (3)

	U11	U22	U33	U12	U13	U23
N2	0.031 (2)	0.021 (2)	0.0189 (19)	−0.0006 (18)	−0.0026 (17)	−0.0048 (16)
N1	0.031 (2)	0.0187 (18)	0.0204 (18)	−0.0053 (17)	−0.0098 (16)	−0.0034 (15)
C1	0.028 (2)	0.017 (2)	0.020 (2)	−0.001 (2)	−0.0027 (19)	−0.0056 (18)
C3	0.024 (2)	0.0126 (19)	0.015 (2)	−0.0054 (18)	−0.0029 (18)	−0.0008 (16)
C4	0.023 (2)	0.017 (2)	0.022 (2)	0.0001 (19)	0.0000 (19)	−0.0059 (18)
C6	0.025 (2)	0.023 (2)	0.025 (2)	−0.002 (2)	−0.003 (2)	−0.0097 (19)
C5	0.022 (2)	0.018 (2)	0.029 (2)	−0.0011 (19)	−0.008 (2)	−0.0029 (19)
C2	0.023 (2)	0.016 (2)	0.022 (2)	0.0010 (19)	−0.0046 (18)	−0.0052 (18)
Cl1	0.0244 (6)	0.0273 (6)	0.0235 (5)	0.0001 (5)	−0.0081 (4)	−0.0108 (4)

N2—C6	1.225 (7)	C3—C4	1.437 (7)
N1—C5	1.371 (7)	C3—C6	1.473 (8)
N1—C1	1.379 (6)	C4—C5	1.398 (8)
N1—H1	0.8999	C4—H4A	0.9500
C1—C2	1.404 (8)	C5—H5A	0.9500
C1—H1A	0.9500	C2—H2A	0.9500
C3—C2	1.430 (7)
C5—N1—C1	122.5 (5)	C5—C4—H4A	121.0
C5—N1—H1	118.8	C3—C4—H4A	121.0
C1—N1—H1	118.8	N2—C6—C3	177.9 (5)
N1—C1—C2	119.9 (5)	N1—C5—C4	120.7 (4)
N1—C1—H1A	120.0	N1—C5—H5A	119.6
C2—C1—H1A	120.0	C4—C5—H5A	119.6
C2—C3—C4	120.3 (5)	C1—C2—C3	118.5 (4)
C2—C3—C6	118.9 (4)	C1—C2—H2A	120.7
C4—C3—C6	120.8 (5)	C3—C2—H2A	120.7
C5—C4—C3	118.1 (5)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···Cl1i	0.90	2.14	3.033 (5)	174
C4—H4A···Cl1	0.95	2.71	3.566 (5)	151
C5—H5A···Cl1ii	0.95	2.65	3.566 (6)	161

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯Cl1i	0.90	2.14	3.033 (5)	174
C4—H4A⋯Cl1	0.95	2.71	3.566 (5)	151
C5—H5A⋯Cl1ii	0.95	2.65	3.566 (6)	161

Symmetry codes: (i) ; (ii) .