3-(1H-Tetra-zol-5-yl)pyridinium chloride.

In the cation of the title compound, C(6)H(6)N(5) (+)·Cl(-), the pyridinium and tetra-zole rings are nearly coplanar, making a dihedral angle of 5.05 (12)°. The cations and anions are connected by inter-molecular N-H⋯Cl hydrogen bonds, forming a centrosymmetric [2 + 2] aggregate. The aggregates are stacked along the a axis.

Related literature

For applications of tetra­zole derivatives in coordination chemistry, see: Xiong et al. (2002 ▶); Wang et al. (2005 ▶). For the crystal structures of related compounds, see: Dai & Fu (2008 ▶); Wen (2008 ▶).

Experimental

Crystal data

C6H6N5 +·Cl−

M = 183.61

Monoclinic,

a = 4.2741 (9) Å

b = 8.1992 (16) Å

c = 23.559 (5) Å

β = 94.72 (3)°

V = 822.8 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.41 mm−1

T = 298 K

0.30 × 0.25 × 0.20 mm

Data collection

Rigaku Mercury2 diffractometer

Absorption correction: multi-scan (; Rigaku, 2005 ▶) T min = 0.883, T max = 0.921

8164 measured reflections

1862 independent reflections

1431 reflections with I > 2σ(I)

R int = 0.041

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.104

S = 1.03

1862 reflections

109 parameters

H-atom parameters constrained

Δρmax = 0.22 e Å−3

Δρmin = −0.28 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/S1600536809018972/is2410sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809018972/is2410Isup2.hkl

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

C6H6N5+·Cl−	F(000) = 376
Mr = 183.61	Dx = 1.482 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1862 reflections
a = 4.2741 (9) Å	θ = 3.0–27.3°
b = 8.1992 (16) Å	µ = 0.41 mm−1
c = 23.559 (5) Å	T = 298 K
β = 94.72 (3)°	Block, colorless
V = 822.8 (3) Å3	0.30 × 0.25 × 0.20 mm
Z = 4

Rigaku Mercury2 diffractometer	1862 independent reflections
Radiation source: fine-focus sealed tube	1431 reflections with I > 2σ(I)
graphite	Rint = 0.041
Detector resolution: 13.6612 pixels mm-1	θmax = 27.3°, θmin = 3.0°
ω scans	h = −5→5
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −10→10
Tmin = 0.883, Tmax = 0.921	l = −30→30
8164 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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.104	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0463P)2 + 0.2136P] where P = (Fo2 + 2Fc2)/3
1862 reflections	(Δ/σ)max < 0.001
109 parameters	Δρmax = 0.22 e Å−3
0 restraints	Δρmin = −0.28 e Å−3

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	0.08068 (11)	0.24606 (6)	0.463087 (19)	0.04954 (18)
N1	0.4537 (4)	0.72566 (17)	0.43139 (6)	0.0410 (4)
H1A	0.5437	0.7521	0.4641	0.049*
N2	0.6191 (4)	0.25335 (16)	0.35565 (6)	0.0389 (4)
H2	0.7389	0.2624	0.3867	0.047*
N3	0.5985 (4)	0.12105 (19)	0.32164 (7)	0.0467 (4)
N4	0.3940 (4)	0.1567 (2)	0.27942 (7)	0.0495 (4)
N5	0.2793 (4)	0.31072 (19)	0.28532 (7)	0.0446 (4)
C1	0.5092 (4)	0.5771 (2)	0.41068 (7)	0.0365 (4)
H1	0.6408	0.5050	0.4317	0.044*
C2	0.3697 (4)	0.53090 (19)	0.35769 (6)	0.0307 (4)
C3	0.1717 (4)	0.6434 (2)	0.32759 (7)	0.0373 (4)
H3	0.0751	0.6155	0.2921	0.045*
C4	0.1194 (5)	0.7958 (2)	0.35038 (8)	0.0444 (5)
H4	−0.0111	0.8704	0.3304	0.053*
C5	0.2639 (5)	0.8356 (2)	0.40346 (8)	0.0465 (5)
H5	0.2301	0.9370	0.4196	0.056*
C6	0.4224 (4)	0.3690 (2)	0.33340 (7)	0.0322 (4)

	U11	U22	U33	U12	U13	U23
Cl1	0.0494 (3)	0.0611 (3)	0.0360 (3)	0.0092 (2)	−0.0094 (2)	−0.0010 (2)
N1	0.0493 (9)	0.0431 (9)	0.0296 (8)	0.0010 (7)	−0.0028 (7)	−0.0053 (6)
N2	0.0425 (8)	0.0389 (8)	0.0337 (8)	0.0066 (6)	−0.0069 (6)	−0.0040 (6)
N3	0.0535 (9)	0.0397 (9)	0.0459 (9)	0.0048 (7)	−0.0019 (7)	−0.0063 (7)
N4	0.0576 (10)	0.0420 (9)	0.0468 (9)	0.0019 (7)	−0.0084 (8)	−0.0098 (7)
N5	0.0528 (9)	0.0392 (8)	0.0391 (8)	0.0018 (7)	−0.0121 (7)	−0.0045 (7)
C1	0.0395 (9)	0.0390 (9)	0.0298 (8)	0.0035 (7)	−0.0042 (7)	0.0021 (7)
C2	0.0321 (8)	0.0331 (8)	0.0265 (8)	−0.0003 (7)	0.0003 (6)	0.0011 (6)
C3	0.0392 (9)	0.0402 (9)	0.0311 (8)	0.0015 (7)	−0.0048 (7)	0.0028 (7)
C4	0.0473 (11)	0.0400 (10)	0.0450 (11)	0.0090 (8)	−0.0014 (9)	0.0073 (8)
C5	0.0560 (12)	0.0356 (10)	0.0482 (11)	0.0051 (9)	0.0066 (9)	−0.0025 (9)
C6	0.0319 (8)	0.0355 (9)	0.0286 (8)	0.0000 (7)	−0.0009 (6)	0.0030 (7)

N1—C1	1.340 (2)	C1—C2	1.391 (2)
N1—C5	1.348 (2)	C1—H1	0.9300
N1—H1A	0.8600	C2—C3	1.404 (2)
N2—C6	1.345 (2)	C2—C6	1.470 (2)
N2—N3	1.347 (2)	C3—C4	1.385 (3)
N2—H2	0.8600	C3—H3	0.9300
N3—N4	1.302 (2)	C4—C5	1.387 (3)
N4—N5	1.366 (2)	C4—H4	0.9300
N5—C6	1.331 (2)	C5—H5	0.9300
C1—N1—C5	123.19 (15)	C2—C3—H3	119.8
C1—N1—H1A	118.4	N4—N3—N2	106.29 (14)
C5—N1—H1A	118.4	C3—C4—C5	119.18 (16)
N1—C1—C2	119.91 (15)	C3—C4—H4	120.4
N1—C1—H1	120.0	C5—C4—H4	120.4
C2—C1—H1	120.0	N3—N4—N5	110.72 (14)
C1—C2—C3	118.05 (16)	C6—N5—N4	105.96 (14)
C1—C2—C6	121.81 (14)	N1—C5—C4	119.22 (17)
C3—C2—C6	120.13 (14)	N1—C5—H5	120.4
C6—N2—N3	109.14 (14)	C4—C5—H5	120.4
C6—N2—H2	125.4	N5—C6—N2	107.90 (15)
N3—N2—H2	125.4	N5—C6—C2	125.52 (15)
C4—C3—C2	120.44 (16)	N2—C6—C2	126.58 (14)
C4—C3—H3	119.8

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···Cl1i	0.86	2.25	3.0625 (18)	157
N2—H2···Cl1ii	0.86	2.23	3.0790 (18)	171

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯Cl1i	0.86	2.25	3.0625 (18)	157
N2—H2⋯Cl1ii	0.86	2.23	3.0790 (18)	171

Symmetry codes: (i) ; (ii) .