2-(2H-Tetra-zol-5-yl)pyridinium nitrate.

In the cation of the title compound, C(6)H(6)N(5) (+)·NO(3) (-), the dihedral angle between the pyridinium and tetra-zole rings is 8.2 (2)°. The constituent ions of the compound are linked via N-H⋯O hydrogen bonds, forming helical chains running along the b axis. C-H⋯N and C-H⋯O hydrogen bonds are also observed.

Related literature

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

Experimental

Crystal data

C6H6N5 +·NO3 −

M = 210.17

Monoclinic,

a = 20.400 (4) Å

b = 4.8981 (10) Å

c = 19.135 (4) Å

β = 114.77 (3)°

V = 1736.1 (7) Å3

Z = 8

Mo Kα radiation

μ = 0.13 mm−1

T = 298 K

0.20 × 0.15 × 0.15 mm

Data collection

Rigaku Mercury2 diffractometer

Absorption correction: multi-scan (CrystalClear, Rigaku, 2005 ▶) T min = 0.976, T max = 0.980

8427 measured reflections

1999 independent reflections

1033 reflections with I > 2σ(I)

R int = 0.123

Refinement

R[F 2 > 2σ(F 2)] = 0.081

wR(F 2) = 0.209

S = 1.04

1999 reflections

136 parameters

H-atom parameters constrained

Δρmax = 0.34 e Å−3

Δρmin = −0.36 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/S1600536809018078/ci2780sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809018078/ci2780Isup2.hkl

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

C6H6N5+·NO3−	F(000) = 864
Mr = 210.17	Dx = 1.608 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 1999 reflections
a = 20.400 (4) Å	θ = 3.8–27.5°
b = 4.8981 (10) Å	µ = 0.13 mm−1
c = 19.135 (4) Å	T = 298 K
β = 114.77 (3)°	Block, colourless
V = 1736.1 (7) Å3	0.20 × 0.15 × 0.15 mm
Z = 8

Rigaku Mercury2 diffractometer	1999 independent reflections
Radiation source: fine-focus sealed tube	1033 reflections with I > 2σ(I)
graphite	Rint = 0.123
Detector resolution: 13.6612 pixels mm-1	θmax = 27.5°, θmin = 3.8°
ω scans	h = −26→26
Absorption correction: multi-scan (CrystalClear, Rigaku, 2005)	k = −6→6
Tmin = 0.976, Tmax = 0.980	l = −24→24
8427 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)] = 0.081	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.209	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0838P)2] where P = (Fo2 + 2Fc2)/3
1999 reflections	(Δ/σ)max = 0.001
136 parameters	Δρmax = 0.34 e Å−3
0 restraints	Δρmin = −0.36 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
N1	0.11658 (15)	0.9420 (6)	0.51774 (16)	0.0383 (7)
H1	0.1239	1.0055	0.5623	0.046*
C6	0.21176 (18)	0.6182 (7)	0.58420 (19)	0.0362 (8)
N2	0.24979 (17)	0.3908 (6)	0.58539 (17)	0.0485 (8)
C1	0.15732 (18)	0.7297 (7)	0.51387 (19)	0.0364 (8)
N5	0.23230 (16)	0.7307 (6)	0.65302 (17)	0.0447 (8)
C3	0.0917 (2)	0.7442 (8)	0.3768 (2)	0.0506 (10)
H3	0.0831	0.6771	0.3283	0.061*
N4	0.28398 (16)	0.5624 (6)	0.69580 (17)	0.0463 (8)
H4A	0.3082	0.5846	0.7445	0.056*
N3	0.29538 (17)	0.3572 (7)	0.65769 (18)	0.0518 (9)
C4	0.0518 (2)	0.9615 (9)	0.3841 (2)	0.0520 (11)
H4	0.0161	1.0411	0.3408	0.062*
C2	0.14442 (19)	0.6270 (8)	0.4418 (2)	0.0436 (9)
H2	0.1711	0.4798	0.4371	0.052*
C5	0.0657 (2)	1.0571 (8)	0.4558 (2)	0.0446 (9)
H5	0.0395	1.2039	0.4615	0.053*
N6	0.41263 (16)	0.8821 (6)	0.85439 (18)	0.0434 (8)
O3	0.37035 (14)	0.6773 (5)	0.84530 (13)	0.0533 (8)
O2	0.44457 (14)	0.9758 (6)	0.91958 (15)	0.0570 (8)
O1	0.41958 (16)	0.9759 (6)	0.79835 (16)	0.0672 (9)

	U11	U22	U33	U12	U13	U23
N1	0.0387 (17)	0.0438 (18)	0.0341 (16)	−0.0043 (14)	0.0169 (14)	−0.0018 (14)
C6	0.0362 (19)	0.037 (2)	0.038 (2)	−0.0036 (17)	0.0179 (16)	−0.0003 (16)
N2	0.0487 (19)	0.054 (2)	0.0364 (18)	0.0079 (16)	0.0115 (15)	−0.0008 (15)
C1	0.0372 (19)	0.039 (2)	0.036 (2)	−0.0052 (16)	0.0181 (17)	−0.0005 (16)
N5	0.0421 (18)	0.0480 (19)	0.0379 (18)	0.0021 (15)	0.0108 (14)	−0.0026 (15)
C3	0.057 (3)	0.058 (3)	0.038 (2)	−0.015 (2)	0.020 (2)	−0.0046 (19)
N4	0.0434 (18)	0.0510 (19)	0.0352 (17)	−0.0010 (16)	0.0073 (14)	−0.0014 (16)
N3	0.047 (2)	0.055 (2)	0.049 (2)	0.0072 (17)	0.0154 (17)	−0.0032 (16)
C4	0.041 (2)	0.068 (3)	0.038 (2)	−0.009 (2)	0.0078 (18)	0.009 (2)
C2	0.042 (2)	0.049 (2)	0.043 (2)	−0.0064 (18)	0.0212 (18)	−0.0027 (18)
C5	0.040 (2)	0.046 (2)	0.045 (2)	−0.0021 (17)	0.0155 (19)	0.0074 (18)
N6	0.0382 (18)	0.049 (2)	0.0414 (19)	0.0006 (15)	0.0156 (15)	−0.0023 (16)
O3	0.0543 (17)	0.0578 (17)	0.0413 (16)	−0.0174 (14)	0.0136 (13)	−0.0034 (13)
O2	0.0527 (18)	0.070 (2)	0.0460 (17)	−0.0192 (14)	0.0180 (14)	−0.0189 (14)
O1	0.077 (2)	0.080 (2)	0.0499 (17)	−0.0107 (17)	0.0314 (16)	0.0090 (16)

N1—C5	1.329 (4)	C3—H3	0.93
N1—C1	1.352 (4)	N4—N3	1.318 (4)
N1—H1	0.86	N4—H4A	0.86
C6—N5	1.323 (4)	C4—C5	1.363 (5)
C6—N2	1.352 (4)	C4—H4	0.93
C6—C1	1.446 (5)	C2—H2	0.93
N2—N3	1.314 (4)	C5—H5	0.93
C1—C2	1.386 (5)	N6—O1	1.228 (3)
N5—N4	1.318 (4)	N6—O2	1.229 (4)
C3—C4	1.382 (5)	N6—O3	1.286 (4)
C3—C2	1.383 (5)
C5—N1—C1	123.0 (3)	N5—N4—H4A	122.8
C5—N1—H1	118.5	N3—N4—H4A	122.8
C1—N1—H1	118.5	N2—N3—N4	106.0 (3)
N5—C6—N2	112.7 (3)	C5—C4—C3	118.9 (4)
N5—C6—C1	124.7 (3)	C5—C4—H4	120.5
N2—C6—C1	122.6 (3)	C3—C4—H4	120.5
N3—N2—C6	105.6 (3)	C3—C2—C1	119.8 (4)
N1—C1—C2	117.9 (3)	C3—C2—H2	120.1
N1—C1—C6	119.3 (3)	C1—C2—H2	120.1
C2—C1—C6	122.8 (3)	N1—C5—C4	120.5 (4)
N4—N5—C6	101.3 (3)	N1—C5—H5	119.8
C4—C3—C2	119.8 (4)	C4—C5—H5	119.8
C4—C3—H3	120.1	O1—N6—O2	122.7 (3)
C2—C3—H3	120.1	O1—N6—O3	119.3 (3)
N5—N4—N3	114.4 (3)	O2—N6—O3	118.0 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O3i	0.86	1.92	2.772 (4)	172
N4—H4A···O3	0.86	1.87	2.717 (4)	170
C2—H2···N2ii	0.93	2.58	3.507 (5)	173
C3—H3···O1iii	0.93	2.52	3.435 (5)	171
C5—H5···O2i	0.93	2.54	3.218 (5)	130
C5—H5···O2iv	0.93	2.36	3.223 (5)	155

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O3i	0.86	1.92	2.772 (4)	172
N4—H4A⋯O3	0.86	1.87	2.717 (4)	170
C2—H2⋯N2ii	0.93	2.58	3.507 (5)	173
C3—H3⋯O1iii	0.93	2.52	3.435 (5)	171
C5—H5⋯O2i	0.93	2.54	3.218 (5)	130
C5—H5⋯O2iv	0.93	2.36	3.223 (5)	155

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