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

In the cation of the title compound, C(6)H(6)N(5) (+)·ClO(4) (-), the pyridinium and tetra-zole rings form a dihedral angle of 23.6 (1)°. In the crystal structure, weak inter-molecular N-H⋯O and N-H⋯N hydrogen bonds link cations and anions into chains extending along the b axis.

Related literature

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

Experimental

Crystal data

C6H6N5 +·ClO4 −

M = 247.61

Monoclinic,

a = 5.2033 (10) Å

b = 14.764 (3) Å

c = 12.244 (2) Å

β = 101.78 (3)°

V = 920.8 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.43 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 = 0.872, T max = 1.000 (expected range = 0.801–0.919)

9546 measured reflections

2108 independent reflections

1849 reflections with I > 2σ(I)

R int = 0.036

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.093

S = 1.09

2108 reflections

146 parameters

H-atom parameters constrained

Δρmax = 0.29 e Å−3

Δρmin = −0.37 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/S1600536809018200/cv2545sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809018200/cv2545Isup2.hkl

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

C6H6N5+·ClO4−	F(000) = 504
Mr = 247.61	Dx = 1.786 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2108 reflections
a = 5.2033 (10) Å	θ = 3.2–27.5°
b = 14.764 (3) Å	µ = 0.43 mm−1
c = 12.244 (2) Å	T = 298 K
β = 101.78 (3)°	Block, colourless
V = 920.8 (3) Å3	0.30 × 0.25 × 0.20 mm
Z = 4

Rigaku Mercury2 diffractometer	2108 independent reflections
Radiation source: fine-focus sealed tube	1849 reflections with I > 2σ(I)
graphite	Rint = 0.036
Detector resolution: 13.6612 pixels mm-1	θmax = 27.5°, θmin = 3.2°
CCD profile fitting scans	h = −6→6
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −19→19
Tmin = 0.872, Tmax = 1.000	l = −15→15
9546 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)] = 0.035	H-atom parameters constrained
wR(F2) = 0.093	w = 1/[σ2(Fo2) + (0.0391P)2 + 0.4636P] where P = (Fo2 + 2Fc2)/3
S = 1.09	(Δ/σ)max < 0.001
2108 reflections	Δρmax = 0.29 e Å−3
146 parameters	Δρmin = −0.37 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: 0.032 (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	0.54774 (8)	0.68556 (3)	0.60933 (3)	0.02861 (15)
O4	0.6154 (3)	0.76134 (10)	0.54624 (12)	0.0425 (4)
O3	0.2704 (3)	0.68626 (10)	0.60633 (13)	0.0433 (4)
O2	0.6150 (3)	0.60331 (10)	0.55912 (15)	0.0524 (4)
N1	0.3679 (3)	0.59831 (10)	0.88383 (13)	0.0307 (3)
N5	0.0708 (3)	0.33991 (11)	0.61681 (12)	0.0317 (3)
H5A	−0.0101	0.3029	0.5673	0.038*
N4	0.7318 (3)	0.51759 (10)	0.89177 (13)	0.0325 (4)
C3	0.3301 (3)	0.45759 (11)	0.77061 (13)	0.0247 (3)
C6	0.4761 (3)	0.52315 (11)	0.85006 (13)	0.0246 (3)
N2	0.5614 (3)	0.64262 (10)	0.94760 (13)	0.0327 (4)
C5	0.2877 (4)	0.31159 (12)	0.68590 (16)	0.0337 (4)
H5	0.3471	0.2526	0.6810	0.040*
N3	0.7722 (3)	0.59329 (10)	0.95023 (13)	0.0325 (4)
H3A	0.9246	0.6090	0.9871	0.039*
O1	0.6915 (3)	0.69193 (12)	0.72169 (12)	0.0516 (4)
C2	0.0996 (3)	0.48426 (12)	0.69840 (15)	0.0298 (4)
H2	0.0327	0.5423	0.7026	0.036*
C4	0.4234 (4)	0.37000 (12)	0.76447 (15)	0.0308 (4)
H4	0.5756	0.3511	0.8129	0.037*
C1	−0.0268 (4)	0.42336 (13)	0.62097 (15)	0.0334 (4)
H1	−0.1799	0.4401	0.5716	0.040*

	U11	U22	U33	U12	U13	U23
Cl1	0.0264 (2)	0.0283 (2)	0.0283 (2)	−0.00122 (15)	−0.00104 (16)	0.00377 (16)
O4	0.0439 (8)	0.0389 (8)	0.0435 (8)	−0.0015 (6)	0.0060 (6)	0.0151 (6)
O3	0.0268 (7)	0.0536 (9)	0.0482 (8)	−0.0018 (6)	0.0044 (6)	−0.0002 (7)
O2	0.0510 (9)	0.0366 (8)	0.0687 (11)	0.0080 (7)	0.0098 (8)	−0.0074 (7)
N1	0.0302 (8)	0.0249 (8)	0.0349 (8)	−0.0011 (6)	0.0013 (6)	−0.0052 (6)
N5	0.0349 (8)	0.0290 (8)	0.0287 (8)	−0.0066 (6)	0.0006 (6)	−0.0077 (6)
N4	0.0284 (8)	0.0285 (8)	0.0371 (8)	0.0002 (6)	−0.0016 (6)	−0.0049 (6)
C3	0.0260 (8)	0.0227 (8)	0.0247 (8)	−0.0023 (6)	0.0036 (6)	−0.0002 (6)
C6	0.0262 (8)	0.0215 (8)	0.0244 (8)	0.0000 (6)	0.0012 (6)	0.0007 (6)
N2	0.0346 (8)	0.0266 (8)	0.0344 (8)	−0.0041 (6)	0.0014 (6)	−0.0049 (6)
C5	0.0423 (11)	0.0224 (9)	0.0348 (10)	0.0007 (7)	0.0037 (8)	−0.0026 (7)
N3	0.0289 (8)	0.0293 (8)	0.0348 (8)	−0.0038 (6)	−0.0038 (6)	−0.0047 (6)
O1	0.0471 (9)	0.0699 (11)	0.0306 (8)	−0.0147 (7)	−0.0092 (6)	0.0103 (7)
C2	0.0291 (9)	0.0249 (9)	0.0328 (9)	0.0015 (7)	0.0003 (7)	−0.0014 (7)
C4	0.0331 (9)	0.0247 (9)	0.0304 (9)	0.0024 (7)	−0.0030 (7)	−0.0009 (7)
C1	0.0294 (9)	0.0345 (10)	0.0325 (9)	−0.0008 (7)	−0.0027 (7)	−0.0011 (8)

Cl1—O1	1.4285 (15)	C3—C4	1.389 (2)
Cl1—O2	1.4363 (15)	C3—C2	1.394 (2)
Cl1—O3	1.4363 (15)	C3—C6	1.469 (2)
Cl1—O4	1.4433 (14)	N2—N3	1.312 (2)
N1—N2	1.315 (2)	C5—C4	1.375 (2)
N1—C6	1.347 (2)	C5—H5	0.9300
N5—C5	1.332 (2)	N3—H3A	0.8600
N5—C1	1.338 (2)	C2—C1	1.373 (2)
N5—H5A	0.8600	C2—H2	0.9300
N4—N3	1.321 (2)	C4—H4	0.9300
N4—C6	1.327 (2)	C1—H1	0.9300
O1—Cl1—O2	110.02 (11)	N3—N2—N1	105.86 (15)
O1—Cl1—O3	110.48 (10)	N5—C5—C4	119.66 (17)
O2—Cl1—O3	109.06 (9)	N5—C5—H5	120.2
O1—Cl1—O4	109.12 (9)	C4—C5—H5	120.2
O2—Cl1—O4	108.60 (10)	N2—N3—N4	114.64 (14)
O3—Cl1—O4	109.53 (9)	N2—N3—H3A	122.7
N2—N1—C6	105.96 (15)	N4—N3—H3A	122.7
C5—N5—C1	122.96 (15)	C1—C2—C3	118.82 (16)
C5—N5—H5A	118.5	C1—C2—H2	120.6
C1—N5—H5A	118.5	C3—C2—H2	120.6
N3—N4—C6	101.09 (14)	C5—C4—C3	119.14 (16)
C4—C3—C2	119.59 (15)	C5—C4—H4	120.4
C4—C3—C6	120.69 (15)	C3—C4—H4	120.4
C2—C3—C6	119.70 (15)	N5—C1—C2	119.82 (16)
N4—C6—N1	112.45 (15)	N5—C1—H1	120.1
N4—C6—C3	123.79 (15)	C2—C1—H1	120.1
N1—C6—C3	123.66 (15)

D—H···A	D—H	H···A	D···A	D—H···A
N5—H5A···O3i	0.86	2.28	2.964 (2)	136
N5—H5A···N2ii	0.86	2.38	3.059 (2)	136
N3—H3A···O4iii	0.86	2.21	2.884 (2)	135

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N5—H5A⋯O3i	0.86	2.28	2.964 (2)	136
N5—H5A⋯N2ii	0.86	2.38	3.059 (2)	136
N3—H3A⋯O4iii	0.86	2.21	2.884 (2)	135

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