4-Amino-1H-1,2,4-triazol-1-ium nitrate.

The non-centrosymmetric crystal structure of the novel semi-organic title compound, C(2)H(5)N(4) (+)·NO(3) (-), is based on alternating layers of 4-amino-1H-1,2,4-triazolinium cations (formed by parallel chains of cations mediated by weak C-H⋯N hydrogen bonds) and nitrate anions inter-connected via linear and bifurcated N-H⋯O hydrogen bonds and weak C-H⋯O hydrogen bonds. N-H⋯N hydrogen bonds link the anions and cations.

Related literature

For the uses of triazole complexes in medicine, see: Li et al. (2004 ▶); Komeda et al. (2003 ▶); Mernari et al. (1998 ▶); Bentiss et al. (1999 ▶). For the triazole moiety as a part of the ligand system in metal complexes, see: Sinditskii et al. (1987 ▶); Haasnoot (2000 ▶); Klingele & Brooker (2003 ▶); Beckmann & Brooker (2003 ▶); Muller et al. (2003 ▶). For the non-linear optical properties of 4-amino-1,2,4-triazole or 3-amino-1,2,4-triazoles, see: Matulková et al. (2007 ▶, 2008 ▶). For the preparation of 4-amino-1,2,4-triazole, see: Herbert & Garrison (1953 ▶); Matulková et al. (2008 ▶); Sanz et al. (2002 ▶).

Experimental

Crystal data

C2H5N4 +·NO3 −

M = 147.11

Monoclinic,

a = 9.6200 (9) Å

b = 5.2790 (3) Å

c = 11.895 (1) Å

β = 96.667 (3)°

V = 599.99 (8) Å3

Z = 4

Mo Kα radiation

μ = 0.15 mm−1

T = 293 K

0.5 × 0.4 × 0.35 mm

Data collection

Nonius KappaCCD area-detector diffractometer

1867 measured reflections

685 independent reflections

650 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.027

wR(F 2) = 0.073

S = 1.11

685 reflections

92 parameters

2 restraints

H-atom parameters constrained

Δρmax = 0.12 e Å−3

Δρmin = −0.14 e Å−3

Data collection: COLLECT (Hooft, 1998 ▶) and DENZO (Otwin­owski & Minor, 1997 ▶); cell refinement: COLLECT and DENZO; data reduction: COLLECT and DENZO; program(s) used to solve structure: SIR92 (Altomare et al., 1994 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810049949/zq2079sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810049949/zq2079Isup2.hkl

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

C2H5N4+·NO3−	F(000) = 304
Mr = 147.11	Dx = 1.629 Mg m−3
Monoclinic, Cc	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2yc	Cell parameters from 572 reflections
a = 9.6200 (9) Å	θ = 1.0–27.5°
b = 5.2790 (3) Å	µ = 0.15 mm−1
c = 11.895 (1) Å	T = 293 K
β = 96.667 (3)°	Prism, colourless
V = 599.99 (8) Å3	0.5 × 0.4 × 0.35 mm
Z = 4

Nonius KappaCCD area-detector diffractometer	650 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.026
graphite	θmax = 27.5°, θmin = 3.5°
Detector resolution: 9.091 pixels mm-1	h = −11→12
φ and ω scans to fill the Ewald sphere	k = −5→6
1867 measured reflections	l = −15→15
685 independent reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.027	H-atom parameters constrained
wR(F2) = 0.073	w = 1/[σ2(Fo2) + (0.0382P)2 + 0.111P] where P = (Fo2 + 2Fc2)/3
S = 1.11	(Δ/σ)max < 0.001
685 reflections	Δρmax = 0.12 e Å−3
92 parameters	Δρmin = −0.14 e Å−3
2 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: 0.104 (8)

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
N1	0.20255 (19)	0.8902 (4)	0.36897 (16)	0.0454 (5)
N2	0.08599 (18)	0.8575 (3)	0.42181 (14)	0.0378 (4)
H2	0.0630	0.9678	0.4730	0.045*
C3	0.0132 (2)	0.6606 (4)	0.38252 (16)	0.0370 (4)
H3	−0.0698	0.6022	0.4062	0.044*
N4	0.08113 (16)	0.5606 (3)	0.30229 (14)	0.0337 (4)
C5	0.1957 (2)	0.7065 (5)	0.29519 (19)	0.0436 (5)
H5	0.2608	0.6793	0.2444	0.052*
N6	0.0325 (2)	0.3489 (3)	0.23683 (17)	0.0424 (4)
H6A	0.1058	0.2463	0.2131	0.051*
H6B	−0.0266	0.4027	0.1716	0.051*
N7	0.37711 (17)	0.3656 (4)	0.08773 (13)	0.0383 (4)
O1	0.49649 (17)	0.2961 (4)	0.06543 (15)	0.0563 (5)
O2	0.3276 (2)	0.5676 (3)	0.04961 (17)	0.0555 (5)
O3	0.31256 (18)	0.2262 (4)	0.14762 (15)	0.0566 (5)

	U11	U22	U33	U12	U13	U23
N1	0.0350 (9)	0.0525 (10)	0.0509 (10)	−0.0089 (8)	0.0142 (8)	−0.0060 (8)
N2	0.0347 (8)	0.0442 (9)	0.0359 (8)	−0.0036 (7)	0.0096 (6)	−0.0009 (7)
C3	0.0324 (10)	0.0446 (11)	0.0350 (9)	−0.0038 (8)	0.0088 (7)	0.0027 (8)
N4	0.0301 (8)	0.0366 (9)	0.0346 (7)	−0.0019 (6)	0.0052 (6)	0.0008 (6)
C5	0.0345 (10)	0.0488 (12)	0.0497 (12)	−0.0039 (9)	0.0147 (9)	−0.0048 (9)
N6	0.0425 (10)	0.0374 (9)	0.0472 (9)	−0.0025 (7)	0.0049 (7)	−0.0050 (7)
N7	0.0354 (10)	0.0448 (10)	0.0354 (8)	0.0046 (7)	0.0067 (7)	−0.0015 (7)
O1	0.0444 (10)	0.0686 (11)	0.0597 (10)	0.0175 (9)	0.0221 (8)	0.0214 (8)
O2	0.0570 (10)	0.0488 (10)	0.0627 (10)	0.0157 (8)	0.0152 (8)	0.0068 (8)
O3	0.0458 (9)	0.0649 (11)	0.0623 (11)	0.0013 (9)	0.0202 (8)	0.0160 (9)

N1—C5	1.304 (3)	N4—N6	1.411 (2)
N1—N2	1.359 (2)	C5—H5	0.9300
N2—C3	1.309 (3)	N6—H6A	0.9572
N2—H2	0.8888	N6—H6B	0.9506
C3—N4	1.327 (3)	N7—O2	1.232 (3)
C3—H3	0.9300	N7—O3	1.240 (2)
N4—C5	1.355 (3)	N7—O1	1.263 (2)
C5—N1—N2	103.71 (17)	N1—C5—N4	111.00 (18)
C3—N2—N1	111.81 (18)	N1—C5—H5	124.5
C3—N2—H2	126.9	N4—C5—H5	124.5
N1—N2—H2	121.2	N4—N6—H6A	113.8
N2—C3—N4	106.57 (17)	N4—N6—H6B	110.0
N2—C3—H3	126.7	H6A—N6—H6B	108.6
N4—C3—H3	126.7	O2—N7—O3	121.80 (19)
C3—N4—C5	106.89 (17)	O2—N7—O1	119.72 (19)
C3—N4—N6	123.56 (17)	O3—N7—O1	118.48 (19)
C5—N4—N6	129.48 (18)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O1i	0.89	1.83	2.710 (2)	173.
N2—H2···N7i	0.89	2.53	3.315 (2)	148.
N2—H2···O2i	0.89	2.54	3.086 (2)	120.
N6—H6A···O3	0.96	2.22	3.077 (3)	148.
N6—H6B···O3ii	0.95	2.30	3.008 (3)	131.
N6—H6B···O1ii	0.95	2.45	3.112 (3)	126.
N6—H6B···O2iii	0.95	2.59	3.167 (3)	119.
C3—H3···N1iii	0.93	2.45	3.299 (3)	151.
C5—H5···O2	0.93	2.55	3.398 (3)	153.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O1i	0.89	1.83	2.710 (2)	173
N2—H2⋯N7i	0.89	2.53	3.315 (2)	148
N2—H2⋯O2i	0.89	2.54	3.086 (2)	120
N6—H6A⋯O3	0.96	2.22	3.077 (3)	148
N6—H6B⋯O3ii	0.95	2.30	3.008 (3)	131
N6—H6B⋯O1ii	0.95	2.45	3.112 (3)	126
N6—H6B⋯O2iii	0.95	2.59	3.167 (3)	119
C3—H3⋯N1iii	0.93	2.45	3.299 (3)	151
C5—H5⋯O2	0.93	2.55	3.398 (3)	153

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