2-Amino-5-cyano-pyridinium chloride.

In the crystal structure of the title compound, C(6)H(6)N(3) (+)·Cl(-), cohesion is maintained by cation-anion N-H⋯Cl and cation-cation N-H⋯N hydrogen bonds, which link the ions into a three-dimensional network.

Related literature

For the use of tetra­zole derivatives in coordination chemisty, see: Manzur et al. (2007 ▶); Ismayilov et al. (2007 ▶); Austria et al. (2007 ▶).

Experimental

Crystal data

C6H6N3 +·Cl−

M = 155.59

Monoclinic,

a = 4.0937 (8) Å

b = 11.856 (2) Å

c = 14.842 (3) Å

β = 94.95 (3)°

V = 717.7 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.45 mm−1

T = 298 (2) K

0.18 × 0.15 × 0.15 mm

Data collection

Rigaku Mercury2 diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T min = 0.922, T max = 0.935

7307 measured reflections

1652 independent reflections

1252 reflections with I > 2σ(I)

R int = 0.044

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.102

S = 1.06

1652 reflections

91 parameters

H-atom parameters constrained

Δρmax = 0.21 e Å−3

Δρmin = −0.23 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/PC (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL/PC.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808020783/rz2232sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808020783/rz2232Isup2.hkl

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

C6H6N3+·Cl–	F000 = 320
Mr = 155.59	Dx = 1.440 Mg m−3
Monoclinic, P21/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1250 reflections
a = 4.0937 (8) Å	θ = 2.3–24.4º
b = 11.856 (2) Å	µ = 0.45 mm−1
c = 14.842 (3) Å	T = 298 (2) K
β = 94.95 (3)º	Block, colourless
V = 717.7 (2) Å3	0.18 × 0.15 × 0.15 mm
Z = 4

Rigaku Mercury2 diffractometer	1652 independent reflections
Radiation source: fine-focus sealed tube	1252 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.044
Detector resolution: 13.6612 pixels mm-1	θmax = 27.5º
T = 298(2) K	θmin = 3.3º
ω scans	h = −5→5
Absorption correction: multi-scan(CrystalClear; Rigaku, 2005)	k = −15→15
Tmin = 0.922, Tmax = 0.935	l = −19→19
7307 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.045	H-atom parameters constrained
wR(F2) = 0.102	w = 1/[σ2(Fo2) + (0.041P)2 + 0.2213P] where P = (Fo2 + 2Fc2)/3
S = 1.06	(Δ/σ)max < 0.001
1652 reflections	Δρmax = 0.21 e Å−3
91 parameters	Δρmin = −0.23 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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.

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 > σ(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
Cl1	0.44244 (14)	0.60704 (5)	0.17252 (4)	0.0459 (2)
N2	0.0652 (4)	0.69979 (14)	0.32749 (11)	0.0377 (4)
H2A	0.1041	0.6650	0.2787	0.045*
C2	−0.0884 (5)	0.64335 (18)	0.39019 (14)	0.0385 (5)
H2B	−0.1506	0.5687	0.3801	0.046*
N3	0.3183 (5)	0.85595 (16)	0.27271 (13)	0.0507 (5)
H3A	0.3567	0.8175	0.2256	0.061*
H3B	0.3816	0.9250	0.2777	0.061*
C3	−0.1527 (5)	0.69550 (17)	0.46837 (13)	0.0352 (5)
C1	−0.3034 (6)	0.63422 (18)	0.53757 (15)	0.0442 (5)
C6	0.1619 (5)	0.80885 (17)	0.33739 (13)	0.0355 (5)
C4	−0.0595 (5)	0.81008 (17)	0.48174 (14)	0.0398 (5)
H4A	−0.1029	0.8471	0.5346	0.048*
N1	−0.4184 (6)	0.58515 (18)	0.59282 (14)	0.0626 (6)
C5	0.0921 (5)	0.86506 (17)	0.41756 (15)	0.0414 (5)
H5A	0.1510	0.9403	0.4261	0.050*

	U11	U22	U33	U12	U13	U23
Cl1	0.0522 (3)	0.0472 (3)	0.0398 (3)	0.0063 (3)	0.0124 (2)	−0.0055 (2)
N2	0.0471 (10)	0.0364 (9)	0.0305 (9)	−0.0004 (8)	0.0091 (7)	−0.0073 (7)
C2	0.0442 (12)	0.0344 (11)	0.0376 (11)	−0.0020 (9)	0.0082 (9)	−0.0007 (9)
N3	0.0672 (13)	0.0442 (11)	0.0435 (11)	−0.0080 (10)	0.0207 (10)	−0.0001 (9)
C3	0.0370 (11)	0.0378 (11)	0.0313 (10)	0.0033 (9)	0.0063 (8)	0.0016 (8)
C1	0.0523 (13)	0.0414 (12)	0.0400 (12)	0.0027 (10)	0.0101 (10)	−0.0022 (10)
C6	0.0370 (11)	0.0366 (11)	0.0332 (10)	0.0022 (9)	0.0054 (9)	0.0028 (8)
C4	0.0486 (12)	0.0384 (11)	0.0334 (11)	0.0036 (10)	0.0104 (9)	−0.0066 (9)
N1	0.0862 (16)	0.0547 (13)	0.0514 (12)	−0.0085 (11)	0.0316 (12)	0.0009 (10)
C5	0.0530 (13)	0.0306 (11)	0.0419 (12)	−0.0015 (9)	0.0106 (10)	−0.0060 (9)

N2—C2	1.345 (2)	C3—C4	1.420 (3)
N2—C6	1.356 (3)	C3—C1	1.440 (3)
N2—H2A	0.8600	C1—N1	1.140 (3)
C2—C3	1.360 (3)	C6—C5	1.414 (3)
C2—H2B	0.9300	C4—C5	1.349 (3)
N3—C6	1.323 (3)	C4—H4A	0.9300
N3—H3A	0.8600	C5—H5A	0.9300
N3—H3B	0.8600
C2—N2—C6	123.26 (17)	C4—C3—C1	120.62 (18)
C2—N2—H2A	118.4	N1—C1—C3	179.0 (3)
C6—N2—H2A	118.4	N3—C6—N2	118.60 (18)
N2—C2—C3	120.02 (19)	N3—C6—C5	123.9 (2)
N2—C2—H2B	120.0	N2—C6—C5	117.53 (18)
C3—C2—H2B	120.0	C5—C4—C3	119.85 (18)
C6—N3—H3A	120.0	C5—C4—H4A	120.1
C6—N3—H3B	120.0	C3—C4—H4A	120.1
H3A—N3—H3B	120.0	C4—C5—C6	120.34 (19)
C2—C3—C4	118.98 (18)	C4—C5—H5A	119.8
C2—C3—C1	120.37 (19)	C6—C5—H5A	119.8
C6—N2—C2—C3	−0.3 (3)	C2—C3—C4—C5	−0.4 (3)
N2—C2—C3—C4	0.9 (3)	C1—C3—C4—C5	177.6 (2)
N2—C2—C3—C1	−177.1 (2)	C3—C4—C5—C6	−0.7 (3)
C2—N2—C6—N3	178.4 (2)	N3—C6—C5—C4	−177.9 (2)
C2—N2—C6—C5	−0.8 (3)	N2—C6—C5—C4	1.2 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···Cl1	0.86	2.29	3.0818 (18)	153
N3—H3A···Cl1	0.86	2.65	3.363 (2)	141
N3—H3A···N1i	0.86	2.53	3.046 (3)	120
N3—H3B···Cl1ii	0.86	2.37	3.216 (2)	167

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯Cl1	0.86	2.29	3.0818 (18)	153
N3—H3A⋯Cl1	0.86	2.65	3.363 (2)	141
N3—H3A⋯N1i	0.86	2.53	3.046 (3)	120
N3—H3B⋯Cl1ii	0.86	2.37	3.216 (2)	167

Symmetry codes: (i) ; (ii) .