4-(2H-Tetra-zol-5-yl)pyridinium hydrogen sulfate.

In the cation of the title compound, C(6)H(6)N(5) (+)·HSO(4) (-), the pyridine and tetra-zole rings are close to being co-planar [dihedral angle = 3.98 (7)°]. In the crystal, the ions are linked by O-H⋯O, N-H⋯O and N-H⋯(O,O) hydrogen bonds, resulting in chains.

Related literature

Tetrazoles are excellent ligands for the construction of metal-organic frameworks because of their various coordination modes, see: Fu et al. (2008 ▶); Wang et al. (2005 ▶). For the applications of metal-organic coordination compounds, see: Fu et al. (2007 ▶); Huang et al. (1999 ▶); Liu et al. (1999 ▶); Xie et al. (2003 ▶); Zhang et al. (2001 ▶); Zhang et al. (2000 ▶).

Experimental

Crystal data

C6H6N5 +·HSO4 −

M = 245.23

Triclinic,

a = 6.6515 (13) Å

b = 7.5507 (15) Å

c = 10.072 (2) Å

α = 77.72 (3)°

β = 76.88 (3)°

γ = 79.71 (3)°

V = 476.84 (16) Å3

Z = 2

Mo Kα radiation

μ = 0.35 mm−1

T = 298 K

0.30 × 0.25 × 0.20 mm

Data collection

Rigaku Mercury2 diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T min = 0.910, T max = 1.000 (expected range = 0.848–0.932)

4917 measured reflections

2175 independent reflections

1961 reflections with I > 2σ(I)

R int = 0.055

Refinement

R[F 2 > 2σ(F 2)] = 0.050

wR(F 2) = 0.134

S = 1.07

2175 reflections

146 parameters

H-atom parameters constrained

Δρmax = 0.34 e Å−3

Δρmin = −0.41 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/S1600536809032851/bx2220sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809032851/bx2220Isup2.hkl

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

C6H6N5+·HSO4−	Z = 2
Mr = 245.23	F(000) = 252
Triclinic, P1	Dx = 1.708 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.6515 (13) Å	Cell parameters from 1961 reflections
b = 7.5507 (15) Å	θ = 3.2–27.5°
c = 10.072 (2) Å	µ = 0.35 mm−1
α = 77.72 (3)°	T = 298 K
β = 76.88 (3)°	Block, colorless
γ = 79.71 (3)°	0.30 × 0.25 × 0.20 mm
V = 476.84 (16) Å3

Rigaku Mercury2 diffractometer	2175 independent reflections
Radiation source: fine-focus sealed tube	1961 reflections with I > 2σ(I)
graphite	Rint = 0.055
Detector resolution: 13.6612 pixels mm-1	θmax = 27.5°, θmin = 3.2°
CCD profile fitting scans	h = −8→8
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −9→9
Tmin = 0.910, Tmax = 1.000	l = −13→13
4917 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)] = 0.050	H-atom parameters constrained
wR(F2) = 0.134	w = 1/[σ2(Fo2) + (0.0597P)2 + 0.1736P] where P = (Fo2 + 2Fc2)/3
S = 1.07	(Δ/σ)max < 0.001
2175 reflections	Δρmax = 0.34 e Å−3
146 parameters	Δρmin = −0.40 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.137 (14)

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
S1	0.17610 (8)	0.76548 (6)	0.48163 (5)	0.0345 (2)
O2	−0.0454 (3)	0.7896 (2)	0.54236 (17)	0.0469 (4)
O1	0.2068 (3)	0.9101 (2)	0.34498 (15)	0.0469 (4)
H1B	0.1631	1.0128	0.3627	0.070*
C6	0.2581 (3)	0.3789 (3)	0.0215 (2)	0.0321 (4)
N2	0.2528 (3)	0.5615 (2)	−0.00724 (18)	0.0394 (4)
O3	0.2479 (3)	0.5928 (2)	0.43634 (16)	0.0445 (4)
N1	0.2800 (3)	0.0732 (2)	−0.28273 (19)	0.0397 (4)
H1A	0.2824	0.0112	−0.3456	0.048*
O4	0.3022 (3)	0.8031 (2)	0.56937 (19)	0.0537 (5)
N3	0.2423 (3)	0.6128 (3)	0.1106 (2)	0.0438 (5)
N4	0.2414 (3)	0.4632 (3)	0.20321 (19)	0.0447 (5)
H4A	0.2349	0.4630	0.2895	0.054*
N5	0.2511 (3)	0.3125 (3)	0.15493 (18)	0.0444 (5)
C2	0.2855 (3)	0.3527 (3)	−0.2218 (2)	0.0363 (5)
H2	0.2935	0.4774	−0.2472	0.044*
C3	0.2684 (3)	0.2687 (3)	−0.0841 (2)	0.0305 (4)
C4	0.2597 (3)	0.0814 (3)	−0.0490 (2)	0.0374 (5)
H4	0.2498	0.0217	0.0426	0.045*
C5	0.2661 (4)	−0.0136 (3)	−0.1518 (2)	0.0415 (5)
H5	0.2606	−0.1389	−0.1303	0.050*
C1	0.2904 (4)	0.2516 (3)	−0.3202 (2)	0.0395 (5)
H1	0.3010	0.3072	−0.4128	0.047*

	U11	U22	U33	U12	U13	U23
S1	0.0519 (4)	0.0259 (3)	0.0276 (3)	−0.0071 (2)	−0.0060 (2)	−0.00971 (19)
O2	0.0546 (10)	0.0378 (8)	0.0457 (9)	−0.0136 (7)	0.0045 (7)	−0.0116 (7)
O1	0.0696 (11)	0.0312 (8)	0.0346 (8)	−0.0076 (7)	0.0002 (7)	−0.0046 (6)
C6	0.0385 (10)	0.0295 (9)	0.0286 (9)	−0.0064 (8)	−0.0048 (7)	−0.0064 (7)
N2	0.0534 (11)	0.0322 (9)	0.0353 (9)	−0.0087 (8)	−0.0078 (8)	−0.0105 (7)
O3	0.0711 (11)	0.0288 (8)	0.0365 (8)	−0.0053 (7)	−0.0095 (7)	−0.0146 (6)
N1	0.0495 (10)	0.0379 (10)	0.0384 (10)	−0.0063 (8)	−0.0112 (8)	−0.0181 (8)
O4	0.0735 (12)	0.0439 (9)	0.0561 (10)	−0.0003 (8)	−0.0281 (9)	−0.0259 (8)
N3	0.0573 (11)	0.0383 (10)	0.0399 (10)	−0.0082 (8)	−0.0081 (8)	−0.0160 (8)
N4	0.0634 (13)	0.0434 (10)	0.0290 (9)	−0.0042 (9)	−0.0081 (8)	−0.0141 (7)
N5	0.0654 (13)	0.0396 (10)	0.0284 (9)	−0.0074 (9)	−0.0058 (8)	−0.0099 (7)
C2	0.0487 (12)	0.0312 (10)	0.0309 (10)	−0.0111 (9)	−0.0078 (8)	−0.0052 (8)
C3	0.0349 (9)	0.0283 (9)	0.0304 (9)	−0.0050 (7)	−0.0076 (7)	−0.0082 (7)
C4	0.0495 (12)	0.0300 (10)	0.0335 (10)	−0.0082 (9)	−0.0098 (8)	−0.0032 (8)
C5	0.0549 (13)	0.0261 (10)	0.0462 (12)	−0.0066 (9)	−0.0130 (10)	−0.0080 (8)
C1	0.0524 (12)	0.0380 (11)	0.0305 (10)	−0.0098 (9)	−0.0101 (9)	−0.0062 (8)

S1—O3	1.4378 (15)	N3—N4	1.302 (3)
S1—O4	1.4469 (17)	N4—N5	1.315 (3)
S1—O2	1.4564 (17)	N4—H4A	0.8600
S1—O1	1.5623 (16)	C2—C1	1.365 (3)
O1—H1B	0.8200	C2—C3	1.385 (3)
C6—N5	1.324 (3)	C2—H2	0.9300
C6—N2	1.343 (3)	C3—C4	1.392 (3)
C6—C3	1.466 (3)	C4—C5	1.369 (3)
N2—N3	1.309 (2)	C4—H4	0.9300
N1—C1	1.329 (3)	C5—H5	0.9300
N1—C5	1.332 (3)	C1—H1	0.9300
N1—H1A	0.8600
O3—S1—O4	112.84 (10)	N5—N4—H4A	122.5
O3—S1—O2	113.35 (10)	N4—N5—C6	100.98 (18)
O4—S1—O2	112.29 (11)	C1—C2—C3	119.79 (19)
O3—S1—O1	104.09 (9)	C1—C2—H2	120.1
O4—S1—O1	106.97 (11)	C3—C2—H2	120.1
O2—S1—O1	106.53 (10)	C2—C3—C4	119.02 (18)
S1—O1—H1B	109.5	C2—C3—C6	119.51 (18)
N5—C6—N2	112.09 (18)	C4—C3—C6	121.47 (18)
N5—C6—C3	124.79 (18)	C5—C4—C3	118.83 (19)
N2—C6—C3	123.12 (18)	C5—C4—H4	120.6
N3—N2—C6	106.28 (18)	C3—C4—H4	120.6
C1—N1—C5	122.79 (18)	N1—C5—C4	120.08 (19)
C1—N1—H1A	118.6	N1—C5—H5	120.0
C5—N1—H1A	118.6	C4—C5—H5	120.0
N4—N3—N2	105.63 (17)	N1—C1—C2	119.5 (2)
N3—N4—N5	115.02 (17)	N1—C1—H1	120.3
N3—N4—H4A	122.5	C2—C1—H1	120.3
C6—N2—N3—N4	−0.1 (2)	C3—C4—C5—N1	−0.1 (3)
N2—N3—N4—N5	0.1 (3)	N4—N5—C6—N2	0.0 (2)
N3—N4—N5—C6	−0.1 (3)	N4—N5—C6—C3	−179.4 (2)
C5—N1—C1—C2	−0.4 (3)	N3—N2—C6—N5	0.0 (2)
N1—C1—C2—C3	−0.4 (3)	N3—N2—C6—C3	179.51 (19)
C1—C2—C3—C4	0.9 (3)	C2—C3—C6—N5	−176.8 (2)
C1—C2—C3—C6	−178.5 (2)	C4—C3—C6—N5	3.8 (3)
C2—C3—C4—C5	−0.7 (3)	C2—C3—C6—N2	3.7 (3)
C6—C3—C4—C5	178.7 (2)	C4—C3—C6—N2	−175.68 (19)
C1—N1—C5—C4	0.7 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1B···O2i	0.82	1.90	2.694 (2)	163
N1—H1A···O4ii	0.86	1.91	2.736 (2)	159
N4—H4A···O2iii	0.86	2.57	3.033 (3)	115
N4—H4A···O3	0.86	1.97	2.741 (2)	150

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1B⋯O2i	0.82	1.90	2.694 (2)	163
N1—H1A⋯O4ii	0.86	1.91	2.736 (2)	159
N4—H4A⋯O2iii	0.86	2.57	3.033 (3)	115
N4—H4A⋯O3	0.86	1.97	2.741 (2)	150

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