2-Amino-5-(1H-tetra-zol-5-yl)pyridin-1-ium nitrate.

In the cation of the title compound, C(6)H(7)N(6) (+)·NO(3) (-), the pyridine and tetra-zole rings are essentially coplanar, exhibiting a dihedral angle of 6.30 (6)°. In the crystal structure, N-H⋯O, N-H⋯N, C-H⋯O and C-H⋯N hydrogen bonds form a three-dimensional network.

Related literature

For general background on the chemistry of tetra­zole derivatives, see: Dunica et al. (1991 ▶); Wittenberger & Donner (1993 ▶); Zou et al. (2007 ▶); Xiong et al. (2002 ▶). For the crystal structures of related compounds, see: Dai & Fu (2008 ▶); Wang et al. (2005 ▶).

Experimental

Crystal data

C6H7N6 +·NO3 −

M = 225.19

Monoclinic,

a = 8.3797 (17) Å

b = 6.9314 (14) Å

c = 15.881 (3) Å

β = 94.31 (3)°

V = 919.8 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.13 mm−1

T = 298 (2) K

0.30 × 0.22 × 0.20 mm

Data collection

Rigaku Mercury2 diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T min = 0.916, T max = 0.970

8766 measured reflections

2023 independent reflections

1520 reflections with I > 2σ(I)

R int = 0.041

Refinement

R[F 2 > 2σ(F 2)] = 0.049

wR(F 2) = 0.120

S = 1.07

2023 reflections

173 parameters

All H-atom parameters refined

Δρmax = 0.15 e Å−3

Δρmin = −0.18 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/PC (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL/PC.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808030791/rz2247sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808030791/rz2247Isup2.hkl

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

C6H7N6+·NO3−	F(000) = 464
Mr = 225.19	Dx = 1.626 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1772 reflections
a = 8.3797 (17) Å	θ = 2.4–27.1°
b = 6.9314 (14) Å	µ = 0.13 mm−1
c = 15.881 (3) Å	T = 298 K
β = 94.31 (3)°	Block, colourless
V = 919.8 (3) Å3	0.30 × 0.22 × 0.20 mm
Z = 4

Rigaku Mercury2 (2x2 bin mode) diffractometer	2023 independent reflections
Radiation source: fine-focus sealed tube	1520 reflections with I > 2σ(I)
graphite	Rint = 0.041
Detector resolution: 13.6612 pixels mm-1	θmax = 27.1°, θmin = 3.2°
ω scans	h = −10→10
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −8→8
Tmin = 0.916, Tmax = 0.970	l = −20→20
8766 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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.120	All H-atom parameters refined
S = 1.07	w = 1/[σ2(Fo2) + (0.0527P)2 + 0.2064P] where P = (Fo2 + 2Fc2)/3
2023 reflections	(Δ/σ)max < 0.001
173 parameters	Δρmax = 0.15 e Å−3
0 restraints	Δρmin = −0.18 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
O1	0.49052 (18)	0.0891 (2)	0.58329 (9)	0.0552 (4)
O2	0.3288 (2)	0.0420 (2)	0.68089 (9)	0.0632 (5)
O3	0.46287 (18)	0.3054 (2)	0.67890 (10)	0.0588 (4)
N7	0.42643 (19)	0.1424 (2)	0.64808 (10)	0.0406 (4)
N1	0.2311 (2)	0.0535 (2)	0.27752 (10)	0.0416 (4)
C2	0.2037 (2)	0.2485 (3)	0.40803 (11)	0.0359 (4)
C5	0.2593 (2)	0.5628 (3)	0.51712 (11)	0.0401 (4)
N5	0.3153 (2)	0.5556 (2)	0.43967 (10)	0.0427 (4)
C4	0.1695 (2)	0.4035 (3)	0.54193 (12)	0.0411 (5)
C6	0.1714 (2)	0.0831 (3)	0.35207 (11)	0.0367 (4)
N4	0.0781 (2)	−0.0636 (3)	0.36762 (11)	0.0526 (5)
N6	0.2911 (3)	0.7171 (3)	0.56527 (13)	0.0550 (5)
C3	0.1443 (2)	0.2500 (3)	0.48954 (12)	0.0399 (4)
N2	0.1724 (2)	−0.1144 (2)	0.24520 (10)	0.0497 (5)
C1	0.2875 (2)	0.4049 (3)	0.38512 (12)	0.0414 (5)
N3	0.0808 (2)	−0.1835 (3)	0.29971 (11)	0.0577 (5)
H6A	0.345 (3)	0.815 (4)	0.5462 (15)	0.066 (8)*
H6B	0.260 (4)	0.723 (4)	0.618 (2)	0.092 (10)*
H1A	0.306 (3)	0.126 (3)	0.2484 (15)	0.066 (7)*
H4	0.132 (2)	0.408 (3)	0.5949 (13)	0.045 (5)*
H3	0.085 (3)	0.143 (3)	0.5074 (13)	0.052 (6)*
H1	0.325 (3)	0.423 (3)	0.3298 (14)	0.056 (6)*
H5	0.370 (3)	0.658 (3)	0.4211 (14)	0.061 (7)*

	U11	U22	U33	U12	U13	U23
O1	0.0669 (10)	0.0599 (10)	0.0416 (8)	0.0075 (8)	0.0238 (7)	−0.0058 (7)
O2	0.0879 (12)	0.0556 (9)	0.0497 (9)	−0.0239 (9)	0.0292 (9)	−0.0047 (7)
O3	0.0629 (10)	0.0531 (9)	0.0633 (10)	−0.0168 (8)	0.0236 (8)	−0.0186 (7)
N7	0.0451 (9)	0.0430 (9)	0.0345 (8)	0.0031 (7)	0.0084 (7)	−0.0002 (7)
N1	0.0519 (10)	0.0426 (9)	0.0314 (8)	−0.0025 (8)	0.0094 (7)	0.0003 (7)
C2	0.0373 (10)	0.0387 (10)	0.0321 (9)	−0.0009 (8)	0.0055 (7)	0.0016 (8)
C5	0.0445 (10)	0.0413 (11)	0.0344 (9)	0.0030 (8)	0.0015 (8)	−0.0005 (8)
N5	0.0499 (10)	0.0397 (9)	0.0391 (9)	−0.0064 (8)	0.0081 (8)	0.0028 (7)
C4	0.0457 (11)	0.0481 (11)	0.0302 (9)	−0.0006 (9)	0.0077 (8)	0.0010 (8)
C6	0.0395 (10)	0.0406 (10)	0.0306 (9)	−0.0012 (8)	0.0063 (8)	0.0029 (7)
N4	0.0623 (11)	0.0533 (11)	0.0440 (10)	−0.0183 (9)	0.0154 (9)	−0.0049 (8)
N6	0.0739 (14)	0.0439 (11)	0.0475 (11)	−0.0070 (10)	0.0060 (10)	−0.0057 (9)
C3	0.0414 (10)	0.0445 (11)	0.0344 (10)	−0.0052 (9)	0.0076 (8)	0.0037 (8)
N2	0.0650 (11)	0.0454 (10)	0.0392 (9)	−0.0052 (9)	0.0077 (8)	−0.0030 (8)
C1	0.0469 (11)	0.0453 (11)	0.0331 (10)	−0.0040 (9)	0.0101 (8)	0.0021 (8)
N3	0.0750 (13)	0.0515 (11)	0.0475 (10)	−0.0159 (10)	0.0118 (9)	−0.0056 (8)

O1—N7	1.2517 (19)	N5—C1	1.366 (2)
O2—N7	1.221 (2)	N5—H5	0.91 (2)
O3—N7	1.260 (2)	C4—C3	1.358 (3)
N1—C6	1.336 (2)	C4—H4	0.92 (2)
N1—N2	1.350 (2)	C6—N4	1.317 (2)
N1—H1A	0.95 (2)	N4—N3	1.363 (2)
C2—C1	1.356 (3)	N6—H6A	0.88 (3)
C2—C3	1.422 (2)	N6—H6B	0.90 (3)
C2—C6	1.463 (3)	C3—H3	0.95 (2)
C5—N6	1.330 (3)	N2—N3	1.292 (2)
C5—N5	1.350 (2)	C1—H1	0.96 (2)
C5—C4	1.409 (3)
O2—N7—O1	121.71 (17)	C5—C4—H4	117.3 (12)
O2—N7—O3	119.76 (16)	N4—C6—N1	108.35 (17)
O1—N7—O3	118.53 (16)	N4—C6—C2	125.21 (16)
C6—N1—N2	108.63 (16)	N1—C6—C2	126.44 (17)
C6—N1—H1A	131.0 (14)	C6—N4—N3	106.09 (16)
N2—N1—H1A	120.3 (14)	C5—N6—H6A	120.5 (16)
C1—C2—C3	117.54 (18)	C5—N6—H6B	120.9 (19)
C1—C2—C6	122.64 (16)	H6A—N6—H6B	119 (2)
C3—C2—C6	119.82 (17)	C4—C3—C2	120.98 (18)
N6—C5—N5	119.03 (19)	C4—C3—H3	119.4 (13)
N6—C5—C4	123.88 (19)	C2—C3—H3	119.6 (13)
N5—C5—C4	117.09 (17)	N3—N2—N1	106.44 (16)
C5—N5—C1	123.48 (17)	C2—C1—N5	120.56 (17)
C5—N5—H5	119.1 (15)	C2—C1—H1	123.9 (13)
C1—N5—H5	117.4 (15)	N5—C1—H1	115.4 (13)
C3—C4—C5	120.32 (18)	N2—N3—N4	110.49 (17)
C3—C4—H4	122.4 (13)
N6—C5—N5—C1	−179.14 (19)	C2—C6—N4—N3	179.73 (19)
C4—C5—N5—C1	0.9 (3)	C5—C4—C3—C2	−1.7 (3)
N6—C5—C4—C3	−179.0 (2)	C1—C2—C3—C4	0.6 (3)
N5—C5—C4—C3	1.0 (3)	C6—C2—C3—C4	−178.50 (18)
N2—N1—C6—N4	0.7 (2)	C6—N1—N2—N3	−0.4 (2)
N2—N1—C6—C2	−179.74 (18)	C3—C2—C1—N5	1.2 (3)
C1—C2—C6—N4	−173.07 (19)	C6—C2—C1—N5	−179.71 (18)
C3—C2—C6—N4	6.0 (3)	C5—N5—C1—C2	−2.0 (3)
C1—C2—C6—N1	7.5 (3)	N1—N2—N3—N4	0.0 (2)
C3—C2—C6—N1	−173.47 (18)	C6—N4—N3—N2	0.5 (2)
N1—C6—N4—N3	−0.7 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O2i	0.95 (2)	2.55 (2)	3.328 (2)	138.7 (18)
N1—H1A···O3i	0.95 (2)	1.84 (3)	2.764 (2)	163 (2)
N5—H5···O1ii	0.91 (2)	2.11 (2)	2.989 (2)	163 (2)
N5—H5···O3ii	0.91 (2)	2.21 (2)	2.908 (2)	133.3 (19)
N6—H6A···O1iii	0.88 (3)	2.31 (3)	3.074 (3)	145 (2)
N6—H6B···O2iii	0.90 (3)	2.48 (3)	2.908 (2)	110 (2)
N6—H6B···N2iv	0.90 (3)	2.32 (3)	3.176 (3)	158 (3)
C1—H1···O3ii	0.96 (2)	2.60 (2)	3.124 (2)	114.4 (16)
C1—H1···O2i	0.96 (2)	2.38 (2)	3.308 (2)	161.5 (18)
C3—H3···N4v	0.95 (2)	2.55 (2)	3.305 (3)	136.3 (16)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O2i	0.95 (2)	2.55 (2)	3.328 (2)	138.7 (18)
N1—H1A⋯O3i	0.95 (2)	1.84 (3)	2.764 (2)	163 (2)
N5—H5⋯O1ii	0.91 (2)	2.11 (2)	2.989 (2)	163 (2)
N5—H5⋯O3ii	0.91 (2)	2.21 (2)	2.908 (2)	133.3 (19)
N6—H6A⋯O1iii	0.88 (3)	2.31 (3)	3.074 (3)	145 (2)
N6—H6B⋯O2iii	0.90 (3)	2.48 (3)	2.908 (2)	110 (2)
N6—H6B⋯N2iv	0.90 (3)	2.32 (3)	3.176 (3)	158 (3)
C1—H1⋯O3ii	0.96 (2)	2.60 (2)	3.124 (2)	114.4 (16)
C1—H1⋯O2i	0.96 (2)	2.38 (2)	3.308 (2)	161.5 (18)
C3—H3⋯N4v	0.95 (2)	2.55 (2)	3.305 (3)	136.3 (16)

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