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

In the title compound, C(6)H(6)N(5) (+)·Cl(-), the pyridinium and tetra-zole rings are essentially coplanar. The pyridine N atoms are protonated. In the crystal structure, mol-ecules are connected via N-H⋯Cl, C-H⋯Cl, C-H⋯N and N-H⋯N hydrogen bonds into layers that are parallel to the (001) plane. There are two crystallographically independent mol-ecules in the asymmetric unit which are located on mirror planes.

Related literature

For related literature on tetra­zole derivatives, see: Dai & Fu (2008 ▶); Wang et al. (2005 ▶); Wen (2008 ▶); Xiong et al. (2002 ▶).

Experimental

Crystal data

C6H6N5 +·Cl−

M = 183.61

Orthorhombic,

a = 16.375 (3) Å

b = 15.313 (3) Å

c = 6.5176 (13) Å

V = 1634.3 (5) Å3

Z = 8

Mo Kα radiation

μ = 0.41 mm−1

T = 298 (2) K

0.25 × 0.20 × 0.18 mm

Data collection

Rigaku Mercury2 diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T min = 0.910, T max = 0.938

16127 measured reflections

2041 independent reflections

1511 reflections with I > 2σ(I)

R int = 0.076

Refinement

R[F 2 > 2σ(F 2)] = 0.062

wR(F 2) = 0.148

S = 1.14

2041 reflections

145 parameters

H-atom parameters constrained

Δρmax = 0.32 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 (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808032649/nc2115sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808032649/nc2115Isup2.hkl

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

C6H6N5+·Cl−	F(000) = 752
Mr = 183.61	Dx = 1.492 Mg m−3
Orthorhombic, Pbcm	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2c 2b	Cell parameters from 2986 reflections
a = 16.375 (3) Å	θ = 2.5–27.5°
b = 15.313 (3) Å	µ = 0.42 mm−1
c = 6.5176 (13) Å	T = 298 K
V = 1634.3 (5) Å3	Block, colourless
Z = 8	0.25 × 0.20 × 0.18 mm

Rigaku Mercury2 diffractometer	2041 independent reflections
Radiation source: fine-focus sealed tube	1511 reflections with I > 2σ(I)
graphite	Rint = 0.077
Detector resolution: 13.6612 pixels mm-1	θmax = 27.5°, θmin = 2.5°
ω scans	h = −21→21
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −19→19
Tmin = 0.910, Tmax = 0.938	l = −8→8
16127 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)] = 0.062	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.148	H-atom parameters constrained
S = 1.14	w = 1/[σ2(Fo2) + (0.0616P)2 + 0.4596P] where P = (Fo2 + 2Fc2)/3
2041 reflections	(Δ/σ)max < 0.001
145 parameters	Δρmax = 0.32 e Å−3
0 restraints	Δρmin = −0.23 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
C9	0.0640 (2)	0.4651 (2)	0.2500	0.0494 (10)
H9	0.0803	0.5232	0.2500	0.059*
N6	0.26721 (19)	0.3543 (2)	0.2500	0.0476 (8)
N7	0.33865 (17)	0.3973 (2)	0.2500	0.0466 (8)
N8	0.3269 (2)	0.4819 (3)	0.2500	0.0568 (9)
N9	0.24511 (18)	0.4938 (2)	0.2500	0.0480 (8)
H9A	0.2202	0.5432	0.2500	0.058*
C7	0.2096 (2)	0.4149 (2)	0.2500	0.0399 (8)
C8	0.1215 (2)	0.3988 (2)	0.2500	0.0373 (8)
N10	0.09641 (17)	0.31585 (19)	0.2500	0.0422 (8)
H10A	0.1325	0.2750	0.2500	0.051*
C12	0.0174 (2)	0.2938 (3)	0.2500	0.0516 (10)
H12	0.0025	0.2352	0.2500	0.062*
C11	−0.0412 (3)	0.3566 (3)	0.2500	0.0619 (12)
H11	−0.0962	0.3414	0.2500	0.074*
C10	−0.0181 (2)	0.4434 (3)	0.2500	0.0566 (11)
H10	−0.0575	0.4871	0.2500	0.068*
N4	0.4116 (2)	0.8572 (2)	0.2500	0.0671 (11)
N3	0.3635 (2)	0.7880 (2)	0.2500	0.0663 (10)
N2	0.2886 (2)	0.8188 (2)	0.2500	0.0615 (10)
H2	0.2462	0.7856	0.2500	0.074*
N1	0.2836 (2)	0.9048 (2)	0.2500	0.0591 (10)
N5	0.33937 (17)	1.0833 (2)	0.2500	0.0414 (7)
H5A	0.2880	1.0714	0.2500	0.050*
C1	0.3619 (2)	0.9270 (2)	0.2500	0.0422 (9)
C2	0.3931 (2)	1.0162 (2)	0.2500	0.0373 (8)
C3	0.4760 (2)	1.0352 (2)	0.2500	0.0475 (9)
H3	0.5145	0.9905	0.2500	0.057*
C4	0.5005 (2)	1.1221 (3)	0.2500	0.0533 (10)
H4	0.5559	1.1355	0.2500	0.064*
C5	0.4444 (3)	1.1881 (3)	0.2500	0.0546 (11)
H5	0.4611	1.2461	0.2500	0.066*
C6	0.3620 (2)	1.1670 (3)	0.2500	0.0486 (9)
H6	0.3228	1.2110	0.2500	0.058*
Cl1	0.15729 (5)	0.12495 (6)	0.2500	0.0456 (3)
Cl2	0.16485 (7)	0.66996 (7)	0.2500	0.0764 (4)

	U11	U22	U33	U12	U13	U23
C9	0.048 (2)	0.0309 (19)	0.070 (3)	0.0017 (17)	0.000	0.000
N6	0.0410 (18)	0.0434 (19)	0.059 (2)	0.0073 (14)	0.000	0.000
N7	0.0324 (16)	0.052 (2)	0.055 (2)	0.0076 (14)	0.000	0.000
N8	0.0363 (17)	0.061 (2)	0.073 (3)	−0.0044 (15)	0.000	0.000
N9	0.0340 (16)	0.0395 (18)	0.070 (2)	−0.0027 (13)	0.000	0.000
C7	0.041 (2)	0.0356 (19)	0.043 (2)	−0.0021 (16)	0.000	0.000
C8	0.0345 (18)	0.0339 (18)	0.044 (2)	−0.0007 (14)	0.000	0.000
N10	0.0408 (17)	0.0346 (16)	0.051 (2)	0.0027 (13)	0.000	0.000
C12	0.043 (2)	0.043 (2)	0.069 (3)	−0.0116 (18)	0.000	0.000
C11	0.036 (2)	0.059 (3)	0.091 (4)	−0.0024 (19)	0.000	0.000
C10	0.044 (2)	0.047 (2)	0.078 (3)	0.0132 (19)	0.000	0.000
N4	0.047 (2)	0.040 (2)	0.114 (3)	0.0033 (16)	0.000	0.000
N3	0.053 (2)	0.0384 (18)	0.107 (3)	0.0054 (17)	0.000	0.000
N2	0.046 (2)	0.0358 (18)	0.103 (3)	−0.0036 (16)	0.000	0.000
N1	0.0431 (19)	0.0336 (18)	0.100 (3)	0.0011 (14)	0.000	0.000
N5	0.0351 (16)	0.0371 (16)	0.0520 (19)	0.0015 (13)	0.000	0.000
C1	0.0372 (19)	0.0374 (19)	0.052 (2)	0.0022 (16)	0.000	0.000
C2	0.0327 (18)	0.0386 (19)	0.041 (2)	0.0023 (15)	0.000	0.000
C3	0.038 (2)	0.047 (2)	0.058 (3)	0.0049 (17)	0.000	0.000
C4	0.043 (2)	0.053 (2)	0.064 (3)	−0.0091 (19)	0.000	0.000
C5	0.055 (3)	0.039 (2)	0.071 (3)	−0.0112 (19)	0.000	0.000
C6	0.052 (2)	0.035 (2)	0.059 (3)	0.0049 (17)	0.000	0.000
Cl1	0.0394 (5)	0.0403 (5)	0.0572 (6)	−0.0005 (4)	0.000	0.000
Cl2	0.0564 (7)	0.0340 (5)	0.1387 (12)	−0.0022 (5)	0.000	0.000

C9—C8	1.384 (5)	N4—N3	1.320 (5)
C9—C10	1.385 (5)	N4—C1	1.343 (5)
C9—H9	0.9300	N3—N2	1.315 (4)
N6—C7	1.324 (5)	N2—N1	1.320 (4)
N6—N7	1.343 (4)	N2—H2	0.8600
N7—N8	1.309 (5)	N1—C1	1.326 (5)
N8—N9	1.352 (4)	N5—C6	1.335 (5)
N9—C7	1.340 (4)	N5—C2	1.351 (4)
N9—H9A	0.8600	N5—H5A	0.8600
C7—C8	1.464 (5)	C1—C2	1.459 (5)
C8—N10	1.334 (4)	C2—C3	1.389 (5)
N10—C12	1.337 (4)	C3—C4	1.390 (5)
N10—H10A	0.8600	C3—H3	0.9300
C12—C11	1.359 (6)	C4—C5	1.365 (5)
C12—H12	0.9300	C4—H4	0.9300
C11—C10	1.382 (6)	C5—C6	1.387 (5)
C11—H11	0.9300	C5—H5	0.9300
C10—H10	0.9300	C6—H6	0.9300
C8—C9—C10	119.0 (4)	N3—N4—C1	106.1 (3)
C8—C9—H9	120.5	N2—N3—N4	105.5 (3)
C10—C9—H9	120.5	N3—N2—N1	114.6 (3)
C7—N6—N7	106.0 (3)	N3—N2—H2	122.7
N8—N7—N6	111.0 (3)	N1—N2—H2	122.7
N7—N8—N9	106.2 (3)	N2—N1—C1	101.2 (3)
C7—N9—N8	108.0 (3)	C6—N5—C2	123.3 (3)
C7—N9—H9A	126.0	C6—N5—H5A	118.4
N8—N9—H9A	126.0	C2—N5—H5A	118.4
N6—C7—N9	108.9 (3)	N1—C1—N4	112.5 (3)
N6—C7—C8	125.7 (3)	N1—C1—C2	125.3 (3)
N9—C7—C8	125.4 (3)	N4—C1—C2	122.2 (3)
N10—C8—C9	119.3 (3)	N5—C2—C3	118.5 (3)
N10—C8—C7	117.6 (3)	N5—C2—C1	118.9 (3)
C9—C8—C7	123.1 (3)	C3—C2—C1	122.5 (3)
C8—N10—C12	122.6 (3)	C2—C3—C4	118.8 (3)
C8—N10—H10A	118.7	C2—C3—H3	120.6
C12—N10—H10A	118.7	C4—C3—H3	120.6
N10—C12—C11	120.3 (4)	C5—C4—C3	121.0 (4)
N10—C12—H12	119.8	C5—C4—H4	119.5
C11—C12—H12	119.8	C3—C4—H4	119.5
C12—C11—C10	119.1 (4)	C4—C5—C6	118.8 (4)
C12—C11—H11	120.4	C4—C5—H5	120.6
C10—C11—H11	120.4	C6—C5—H5	120.6
C11—C10—C9	119.8 (4)	N5—C6—C5	119.6 (4)
C11—C10—H10	120.1	N5—C6—H6	120.2
C9—C10—H10	120.1	C5—C6—H6	120.2

D—H···A	D—H	H···A	D···A	D—H···A
N9—H9A···Cl2	0.86	2.14	3.001 (3)	177
N10—H10A···Cl1	0.86	2.33	3.088 (3)	147
N2—H2···Cl2	0.86	2.22	3.050 (4)	163
N5—H5A···Cl1i	0.86	2.29	3.049 (3)	147
N5—H5A···N1	0.86	2.55	2.881 (4)	104
N10—H10A···N6	0.86	2.52	2.858 (4)	105
C9—H9···Cl2	0.93	2.64	3.545 (4)	165
C3—H3···N8ii	0.93	2.60	3.329 (5)	136
C6—H6···N6i	0.93	2.38	3.260 (5)	159
C10—H10···Cl1iii	0.93	2.67	3.596 (4)	174

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N9—H9A⋯Cl2	0.86	2.14	3.001 (3)	177
N10—H10A⋯Cl1	0.86	2.33	3.088 (3)	147
N2—H2⋯Cl2	0.86	2.22	3.050 (4)	163
N5—H5A⋯Cl1i	0.86	2.29	3.049 (3)	147
N5—H5A⋯N1	0.86	2.55	2.881 (4)	104
N10—H10A⋯N6	0.86	2.52	2.858 (4)	105
C9—H9⋯Cl2	0.93	2.64	3.545 (4)	165
C3—H3⋯N8ii	0.93	2.60	3.329 (5)	136
C6—H6⋯N6i	0.93	2.38	3.260 (5)	159
C10—H10⋯Cl1iii	0.93	2.67	3.596 (4)	174

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