2-Amino-5-(1H-tetra-zol-5-yl)pyridinium chloride.

In the title salt, C(6)H(7)N(6) (+)·Cl(-), there are two organic cations with similar conformations and two chloride anions in the asymmetric unit. The pyridine and tetra-zole rings are essentially coplanar in each cation, with dihedral angles of 4.94 (15) and 5.41 (14)°. The pyridine N atoms are protonated. The crystal packing is stabilized by N-H⋯N and N-H⋯Cl hydrogen bonds, forming an infinite sheets parallel to the (101).

Related literature

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

Experimental

Crystal data

C6H7N6 +·Cl−

M = 198.63

Monoclinic,

a = 14.043 (3) Å

b = 13.238 (3) Å

c = 9.5766 (19) Å

β = 109.35 (3)°

V = 1679.7 (6) Å3

Z = 8

Mo Kα radiation

μ = 0.41 mm−1

T = 298 (2) K

0.45 × 0.25 × 0.20 mm

Data collection

Rigaku Mercury2 diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T min = 0.859, T max = 0.920

16820 measured reflections

3855 independent reflections

3123 reflections with I > 2σ(I)

R int = 0.034

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.125

S = 1.11

3855 reflections

235 parameters

H-atom parameters constrained

Δρmax = 0.28 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/S1600536808031164/bh2196sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808031164/bh2196Isup2.hkl

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

C6H7N6+·Cl−	F(000) = 816
Mr = 198.63	Dx = 1.571 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3690 reflections
a = 14.043 (3) Å	θ = 2.3–27.5°
b = 13.238 (3) Å	µ = 0.41 mm−1
c = 9.5766 (19) Å	T = 298 K
β = 109.35 (3)°	Block, colorless
V = 1679.7 (6) Å3	0.45 × 0.25 × 0.20 mm
Z = 8

Rigaku Mercury2 diffractometer	3855 independent reflections
Radiation source: fine-focus sealed tube	3123 reflections with I > 2σ(I)
graphite	Rint = 0.034
Detector resolution: 13.6612 pixels mm-1	θmax = 27.5°, θmin = 2.7°
ω scans	h = −18→18
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −17→17
Tmin = 0.859, Tmax = 0.920	l = −12→12
16820 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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.125	H-atom parameters constrained
S = 1.12	w = 1/[σ2(Fo2) + (0.0556P)2 + 0.4684P] where P = (Fo2 + 2Fc2)/3
3855 reflections	(Δ/σ)max < 0.001
235 parameters	Δρmax = 0.28 e Å−3
0 restraints	Δρmin = −0.23 e Å−3

	x	y	z	Uiso*/Ueq
N1	0.56207 (12)	0.65987 (12)	0.17350 (18)	0.0344 (4)
H1	0.5639	0.7245	0.1662	0.041*
N3	0.36346 (13)	0.52444 (13)	0.37792 (19)	0.0368 (4)
H3A	0.3600	0.5892	0.3818	0.044*
C1	0.62505 (14)	0.60404 (14)	0.1236 (2)	0.0313 (4)
N2	0.68458 (13)	0.64965 (13)	0.0611 (2)	0.0413 (4)
H2A	0.6831	0.7143	0.0523	0.050*
H2B	0.7247	0.6146	0.0292	0.050*
N6	0.40734 (13)	0.37577 (12)	0.33322 (19)	0.0382 (4)
N4	0.31050 (14)	0.45963 (13)	0.4305 (2)	0.0428 (4)
C6	0.42266 (14)	0.47298 (14)	0.3184 (2)	0.0310 (4)
N5	0.33724 (14)	0.37053 (13)	0.4030 (2)	0.0430 (4)
C4	0.49237 (14)	0.51714 (13)	0.2516 (2)	0.0304 (4)
C2	0.62316 (14)	0.49827 (14)	0.1406 (2)	0.0333 (4)
H2	0.6657	0.4574	0.1086	0.040*
C3	0.55896 (15)	0.45611 (14)	0.2039 (2)	0.0336 (4)
H3	0.5587	0.3864	0.2160	0.040*
C5	0.49636 (15)	0.61909 (14)	0.2344 (2)	0.0337 (4)
H5	0.4537	0.6610	0.2646	0.040*
N7	0.92034 (13)	0.39582 (12)	0.30105 (18)	0.0364 (4)
H7	0.9131	0.4604	0.2998	0.044*
N9	1.13591 (12)	0.26242 (13)	0.12521 (19)	0.0367 (4)
H9A	1.1409	0.3272	0.1246	0.044*
N8	0.80738 (13)	0.38416 (13)	0.4302 (2)	0.0422 (4)
H8A	0.8043	0.4490	0.4319	0.051*
H8B	0.7726	0.3485	0.4708	0.051*
C7	0.86565 (14)	0.33931 (15)	0.3650 (2)	0.0329 (4)
N10	1.19013 (14)	0.19768 (13)	0.0747 (2)	0.0425 (4)
N12	1.08698 (13)	0.11357 (12)	0.15986 (19)	0.0374 (4)
C12	1.07262 (14)	0.21051 (14)	0.1769 (2)	0.0311 (4)
N11	1.16049 (14)	0.10833 (13)	0.0959 (2)	0.0429 (4)
C10	1.00037 (14)	0.25408 (14)	0.2397 (2)	0.0304 (4)
C9	0.94263 (15)	0.19202 (14)	0.3023 (2)	0.0339 (4)
H9	0.9504	0.1222	0.3025	0.041*
C11	0.98593 (16)	0.35597 (14)	0.2389 (2)	0.0363 (4)
H11	1.0211	0.3983	0.1957	0.044*
C8	0.87624 (15)	0.23312 (15)	0.3618 (2)	0.0337 (4)
H8	0.8378	0.1915	0.4004	0.040*
Cl1	0.84188 (4)	0.97883 (4)	0.45292 (7)	0.04632 (17)
Cl2	0.65611 (4)	0.24380 (4)	0.05567 (6)	0.04478 (17)

	U11	U22	U33	U12	U13	U23
N1	0.0407 (9)	0.0214 (8)	0.0500 (10)	0.0034 (7)	0.0270 (8)	0.0030 (7)
N3	0.0440 (10)	0.0261 (8)	0.0491 (10)	−0.0020 (7)	0.0273 (8)	−0.0008 (7)
C1	0.0332 (10)	0.0274 (9)	0.0362 (10)	0.0024 (7)	0.0157 (8)	0.0009 (7)
N2	0.0483 (11)	0.0305 (9)	0.0589 (11)	0.0027 (7)	0.0363 (9)	0.0028 (8)
N6	0.0456 (10)	0.0267 (8)	0.0507 (10)	−0.0021 (7)	0.0270 (8)	0.0009 (7)
N4	0.0518 (11)	0.0327 (9)	0.0561 (11)	−0.0061 (8)	0.0343 (9)	−0.0012 (8)
C6	0.0334 (10)	0.0265 (9)	0.0358 (10)	−0.0001 (7)	0.0152 (8)	−0.0004 (7)
N5	0.0529 (11)	0.0299 (9)	0.0581 (11)	−0.0034 (8)	0.0346 (9)	−0.0008 (8)
C4	0.0313 (9)	0.0259 (9)	0.0368 (10)	−0.0001 (7)	0.0149 (8)	0.0011 (7)
C2	0.0341 (10)	0.0284 (9)	0.0419 (11)	0.0044 (8)	0.0186 (8)	−0.0002 (8)
C3	0.0368 (10)	0.0238 (9)	0.0422 (11)	0.0017 (7)	0.0158 (8)	−0.0001 (8)
C5	0.0358 (10)	0.0281 (9)	0.0437 (11)	0.0035 (8)	0.0218 (8)	0.0018 (8)
N7	0.0468 (10)	0.0227 (8)	0.0486 (10)	0.0051 (7)	0.0279 (8)	0.0046 (7)
N9	0.0410 (10)	0.0264 (8)	0.0510 (10)	0.0036 (7)	0.0265 (8)	0.0027 (7)
N8	0.0473 (11)	0.0334 (9)	0.0586 (11)	0.0043 (8)	0.0345 (9)	0.0034 (8)
C7	0.0328 (10)	0.0327 (10)	0.0353 (10)	0.0024 (8)	0.0143 (8)	0.0018 (8)
N10	0.0473 (11)	0.0343 (9)	0.0569 (11)	0.0066 (8)	0.0320 (9)	0.0036 (8)
N12	0.0431 (10)	0.0293 (8)	0.0477 (10)	0.0038 (7)	0.0256 (8)	0.0015 (7)
C12	0.0348 (10)	0.0266 (9)	0.0339 (9)	0.0021 (7)	0.0142 (8)	0.0033 (7)
N11	0.0489 (11)	0.0344 (10)	0.0560 (11)	0.0059 (8)	0.0316 (9)	0.0010 (8)
C10	0.0328 (10)	0.0282 (9)	0.0325 (9)	0.0027 (7)	0.0139 (8)	0.0015 (7)
C9	0.0375 (10)	0.0236 (9)	0.0431 (11)	0.0009 (7)	0.0168 (9)	0.0031 (8)
C11	0.0427 (11)	0.0296 (10)	0.0446 (11)	0.0017 (8)	0.0253 (9)	0.0037 (8)
C8	0.0344 (10)	0.0298 (10)	0.0409 (10)	−0.0010 (8)	0.0178 (8)	0.0040 (8)
Cl1	0.0567 (3)	0.0300 (3)	0.0626 (4)	−0.0067 (2)	0.0336 (3)	−0.0052 (2)
Cl2	0.0502 (3)	0.0282 (3)	0.0624 (4)	0.0046 (2)	0.0273 (3)	0.0040 (2)

N1—C1	1.355 (2)	N7—C7	1.355 (2)
N1—C5	1.356 (2)	N7—C11	1.358 (2)
N1—H1	0.8600	N7—H7	0.8600
N3—N4	1.338 (2)	N9—N10	1.339 (2)
N3—C6	1.340 (2)	N9—C12	1.341 (2)
N3—H3A	0.8600	N9—H9A	0.8600
C1—N2	1.325 (2)	N8—C7	1.323 (2)
C1—C2	1.411 (3)	N8—H8A	0.8600
N2—H2A	0.8600	N8—H8B	0.8600
N2—H2B	0.8600	C7—C8	1.415 (3)
N6—C6	1.320 (2)	N10—N11	1.292 (2)
N6—N5	1.362 (2)	N12—C12	1.318 (2)
N4—N5	1.291 (2)	N12—N11	1.365 (2)
C6—C4	1.457 (2)	C12—C10	1.459 (2)
C4—C5	1.363 (3)	C10—C11	1.364 (3)
C4—C3	1.421 (3)	C10—C9	1.419 (3)
C2—C3	1.361 (3)	C9—C8	1.357 (3)
C2—H2	0.9300	C9—H9	0.9300
C3—H3	0.9300	C11—H11	0.9300
C5—H5	0.9300	C8—H8	0.9300
C1—N1—C5	123.42 (16)	C7—N7—C11	123.49 (17)
C1—N1—H1	118.3	C7—N7—H7	118.3
C5—N1—H1	118.3	C11—N7—H7	118.3
N4—N3—C6	109.55 (16)	N10—N9—C12	109.34 (16)
N4—N3—H3A	125.2	N10—N9—H9A	125.3
C6—N3—H3A	125.2	C12—N9—H9A	125.3
N2—C1—N1	119.62 (17)	C7—N8—H8A	120.0
N2—C1—C2	122.91 (17)	C7—N8—H8B	120.0
N1—C1—C2	117.47 (16)	H8A—N8—H8B	120.0
C1—N2—H2A	120.0	N8—C7—N7	119.82 (18)
C1—N2—H2B	120.0	N8—C7—C8	122.80 (18)
H2A—N2—H2B	120.0	N7—C7—C8	117.36 (17)
C6—N6—N5	105.81 (16)	N11—N10—N9	106.13 (15)
N5—N4—N3	105.89 (15)	C12—N12—N11	105.95 (16)
N6—C6—N3	107.67 (16)	N12—C12—N9	107.80 (16)
N6—C6—C4	126.56 (17)	N12—C12—C10	126.32 (17)
N3—C6—C4	125.76 (17)	N9—C12—C10	125.87 (17)
N4—N5—N6	111.08 (16)	N10—N11—N12	110.78 (16)
C5—C4—C3	117.77 (17)	C11—C10—C9	118.05 (17)
C5—C4—C6	120.74 (17)	C11—C10—C12	120.76 (17)
C3—C4—C6	121.49 (16)	C9—C10—C12	121.19 (17)
C3—C2—C1	119.91 (17)	C8—C9—C10	120.89 (17)
C3—C2—H2	120.0	C8—C9—H9	119.6
C1—C2—H2	120.0	C10—C9—H9	119.6
C2—C3—C4	120.90 (17)	N7—C11—C10	120.20 (17)
C2—C3—H3	119.5	N7—C11—H11	119.9
C4—C3—H3	119.5	C10—C11—H11	119.9
N1—C5—C4	120.49 (17)	C9—C8—C7	119.93 (17)
N1—C5—H5	119.8	C9—C8—H8	120.0
C4—C5—H5	119.8	C7—C8—H8	120.0
C5—N1—C1—N2	177.74 (19)	C11—N7—C7—N8	176.37 (19)
C5—N1—C1—C2	−1.8 (3)	C11—N7—C7—C8	−1.9 (3)
C6—N3—N4—N5	0.0 (2)	C12—N9—N10—N11	−0.2 (2)
N5—N6—C6—N3	0.1 (2)	N11—N12—C12—N9	−0.2 (2)
N5—N6—C6—C4	179.20 (18)	N11—N12—C12—C10	179.35 (18)
N4—N3—C6—N6	0.0 (2)	N10—N9—C12—N12	0.3 (2)
N4—N3—C6—C4	−179.15 (19)	N10—N9—C12—C10	−179.30 (18)
N3—N4—N5—N6	0.1 (2)	N9—N10—N11—N12	0.1 (2)
C6—N6—N5—N4	−0.1 (2)	C12—N12—N11—N10	0.1 (2)
N6—C6—C4—C5	175.7 (2)	N12—C12—C10—C11	−173.8 (2)
N3—C6—C4—C5	−5.4 (3)	N9—C12—C10—C11	5.6 (3)
N6—C6—C4—C3	−4.9 (3)	N12—C12—C10—C9	5.7 (3)
N3—C6—C4—C3	173.99 (19)	N9—C12—C10—C9	−174.82 (19)
N2—C1—C2—C3	−178.97 (19)	C11—C10—C9—C8	−1.1 (3)
N1—C1—C2—C3	0.6 (3)	C12—C10—C9—C8	179.35 (18)
C1—C2—C3—C4	0.9 (3)	C7—N7—C11—C10	−0.6 (3)
C5—C4—C3—C2	−1.2 (3)	C9—C10—C11—N7	2.1 (3)
C6—C4—C3—C2	179.48 (19)	C12—C10—C11—N7	−178.31 (18)
C1—N1—C5—C4	1.6 (3)	C10—C9—C8—C7	−1.4 (3)
C3—C4—C5—N1	0.0 (3)	N8—C7—C8—C9	−175.3 (2)
C6—C4—C5—N1	179.36 (18)	N7—C7—C8—C9	2.9 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···N5i	0.86	2.59	3.317 (2)	143
N1—H1···N6i	0.86	2.04	2.894 (2)	171
N2—H2A···N5i	0.86	2.15	2.972 (3)	160
N7—H7···N11ii	0.86	2.57	3.304 (2)	144
N7—H7···N12ii	0.86	2.06	2.913 (2)	169
N8—H8A···N11ii	0.86	2.20	3.024 (3)	160
N2—H2B···Cl1iii	0.86	2.36	3.2187 (18)	177
N3—H3A···Cl2i	0.86	2.17	3.0047 (19)	165
N8—H8B···Cl2iv	0.86	2.39	3.2432 (18)	172
N9—H9A···Cl1v	0.86	2.18	3.0031 (18)	160

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯N5i	0.86	2.59	3.317 (2)	143
N1—H1⋯N6i	0.86	2.04	2.894 (2)	171
N2—H2A⋯N5i	0.86	2.15	2.972 (3)	160
N7—H7⋯N11ii	0.86	2.57	3.304 (2)	144
N7—H7⋯N12ii	0.86	2.06	2.913 (2)	169
N8—H8A⋯N11ii	0.86	2.20	3.024 (3)	160
N2—H2B⋯Cl1iii	0.86	2.36	3.2187 (18)	177
N3—H3A⋯Cl2i	0.86	2.17	3.0047 (19)	165
N8—H8B⋯Cl2iv	0.86	2.39	3.2432 (18)	172
N9—H9A⋯Cl1v	0.86	2.18	3.0031 (18)	160

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