3-Nitro-1H-1,2,4-triazole.

The asymmetric unit of the title compound, C(2)H(2)N(4)O(2), contains two crystallographically independent mol-ecules in which the triazole rings are essentially planar, with maximum deviations of 0.003 (1) Å in both molecules. The dihedral angle between the two 1H-1,2,4-triazole rings is 56.58 (5)°. In the crystal, mol-ecules are linked via inter-molecular N-H⋯N and C-H⋯O hydrogen bonds, forming a supra-molecular chain along the b axis.

Related literature

For details and applications of 1H-1,2,4-triazole derivatives, see: Desenko (1995 ▶); Vos et al. (1983 ▶); van Albada et al. (1984 ▶); Al-Kharafi et al. (1986 ▶); Gupta & Bhargava (1978 ▶); Jones et al. (1965 ▶); Bennur et al. (1976 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C2H2N4O2

M = 114.08

Monoclinic,

a = 8.7818 (1) Å

b = 10.0726 (2) Å

c = 9.9703 (1) Å

β = 107.081 (1)°

V = 843.03 (2) Å3

Z = 8

Mo Kα radiation

μ = 0.16 mm−1

T = 100 K

0.48 × 0.33 × 0.30 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.928, T max = 0.954

11450 measured reflections

3081 independent reflections

2768 reflections with I > 2σ(I)

R int = 0.022

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.092

S = 1.05

3081 reflections

153 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.50 e Å−3

Δρmin = −0.40 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810049287/is2634sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810049287/is2634Isup2.hkl

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

C2H2N4O2	F(000) = 464
Mr = 114.08	Dx = 1.798 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 7180 reflections
a = 8.7818 (1) Å	θ = 2.9–32.6°
b = 10.0726 (2) Å	µ = 0.16 mm−1
c = 9.9703 (1) Å	T = 100 K
β = 107.081 (1)°	Block, colourless
V = 843.03 (2) Å3	0.48 × 0.33 × 0.30 mm
Z = 8

Bruker SMART APEXII CCD area-detector diffractometer	3081 independent reflections
Radiation source: fine-focus sealed tube	2768 reflections with I > 2σ(I)
graphite	Rint = 0.022
φ and ω scans	θmax = 32.7°, θmin = 2.9°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −13→11
Tmin = 0.928, Tmax = 0.954	k = −15→13
11450 measured reflections	l = −15→15

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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.092	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ2(Fo2) + (0.0495P)2 + 0.2412P] where P = (Fo2 + 2Fc2)/3
3081 reflections	(Δ/σ)max = 0.001
153 parameters	Δρmax = 0.50 e Å−3
0 restraints	Δρmin = −0.40 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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
O1A	0.73082 (8)	−0.04055 (7)	0.51717 (7)	0.01914 (13)
O2A	0.85716 (9)	0.01680 (7)	0.73151 (6)	0.01888 (14)
N1A	1.01266 (8)	0.21389 (7)	0.64087 (7)	0.01307 (13)
N2A	0.99857 (9)	0.24376 (7)	0.42001 (7)	0.01273 (13)
N3A	0.89747 (8)	0.14183 (7)	0.41773 (7)	0.01286 (13)
N4A	0.82618 (9)	0.02813 (7)	0.60358 (7)	0.01348 (13)
C1A	1.06543 (10)	0.28585 (8)	0.55150 (8)	0.01356 (14)
H1AA	1.1381	0.3552	0.5768	0.016*
C2A	0.91199 (9)	0.13008 (8)	0.55271 (8)	0.01167 (14)
O1B	0.75840 (8)	0.41600 (7)	0.50676 (7)	0.02046 (14)
O2B	0.68377 (9)	0.58439 (6)	0.60867 (7)	0.01985 (14)
N1B	0.51771 (8)	0.42579 (7)	0.73353 (7)	0.01312 (13)
N2B	0.51813 (9)	0.20833 (7)	0.72132 (7)	0.01419 (13)
N3B	0.60998 (9)	0.24714 (7)	0.64058 (7)	0.01375 (13)
N4B	0.68913 (8)	0.46461 (7)	0.58504 (7)	0.01361 (13)
C1B	0.46484 (10)	0.31423 (8)	0.77581 (8)	0.01436 (15)
H1BA	0.4002	0.3102	0.8347	0.017*
C2B	0.60451 (9)	0.37710 (8)	0.65365 (8)	0.01189 (14)
H1N1	1.0120 (19)	0.2722 (16)	0.3403 (16)	0.034 (4)*
H1N2	0.5028 (18)	0.1259 (16)	0.7343 (15)	0.030 (4)*

	U11	U22	U33	U12	U13	U23
O1A	0.0195 (3)	0.0170 (3)	0.0203 (3)	−0.0044 (2)	0.0049 (2)	−0.0008 (2)
O2A	0.0278 (3)	0.0179 (3)	0.0136 (3)	0.0007 (2)	0.0102 (2)	0.0037 (2)
N1A	0.0164 (3)	0.0135 (3)	0.0103 (3)	−0.0005 (2)	0.0055 (2)	−0.0003 (2)
N2A	0.0164 (3)	0.0133 (3)	0.0099 (3)	0.0001 (2)	0.0060 (2)	0.0011 (2)
N3A	0.0156 (3)	0.0128 (3)	0.0107 (3)	0.0004 (2)	0.0048 (2)	0.0009 (2)
N4A	0.0161 (3)	0.0118 (3)	0.0144 (3)	0.0020 (2)	0.0072 (2)	0.0018 (2)
C1A	0.0163 (3)	0.0142 (3)	0.0115 (3)	−0.0007 (3)	0.0060 (3)	−0.0005 (2)
C2A	0.0146 (3)	0.0109 (3)	0.0107 (3)	0.0013 (2)	0.0056 (2)	0.0010 (2)
O1B	0.0240 (3)	0.0185 (3)	0.0245 (3)	0.0046 (2)	0.0158 (3)	0.0025 (2)
O2B	0.0264 (3)	0.0106 (3)	0.0260 (3)	−0.0006 (2)	0.0131 (3)	0.0004 (2)
N1B	0.0151 (3)	0.0111 (3)	0.0143 (3)	0.0010 (2)	0.0062 (2)	0.0004 (2)
N2B	0.0178 (3)	0.0101 (3)	0.0161 (3)	−0.0002 (2)	0.0072 (2)	0.0006 (2)
N3B	0.0163 (3)	0.0111 (3)	0.0149 (3)	0.0009 (2)	0.0062 (2)	0.0007 (2)
N4B	0.0144 (3)	0.0119 (3)	0.0153 (3)	0.0015 (2)	0.0055 (2)	0.0018 (2)
C1B	0.0166 (3)	0.0119 (3)	0.0160 (3)	0.0006 (3)	0.0070 (3)	0.0005 (2)
C2B	0.0128 (3)	0.0103 (3)	0.0127 (3)	0.0007 (2)	0.0041 (2)	0.0007 (2)

O1A—N4A	1.2241 (10)	O1B—N4B	1.2239 (9)
O2A—N4A	1.2289 (9)	O2B—N4B	1.2329 (9)
N1A—C1A	1.3329 (10)	N1B—C1B	1.3307 (10)
N1A—C2A	1.3455 (10)	N1B—C2B	1.3462 (10)
N2A—C1A	1.3383 (10)	N2B—C1B	1.3421 (10)
N2A—N3A	1.3531 (10)	N2B—N3B	1.3539 (9)
N2A—H1N1	0.885 (15)	N2B—H1N2	0.857 (16)
N3A—C2A	1.3194 (9)	N3B—C2B	1.3178 (10)
N4A—C2A	1.4506 (10)	N4B—C2B	1.4476 (10)
C1A—H1AA	0.9300	C1B—H1BA	0.9300
C1A—N1A—C2A	101.26 (6)	C1B—N1B—C2B	100.99 (7)
C1A—N2A—N3A	110.72 (6)	C1B—N2B—N3B	110.52 (7)
C1A—N2A—H1N1	129.9 (10)	C1B—N2B—H1N2	128.3 (10)
N3A—N2A—H1N1	119.4 (10)	N3B—N2B—H1N2	121.2 (10)
C2A—N3A—N2A	100.64 (6)	C2B—N3B—N2B	100.52 (6)
O1A—N4A—O2A	125.11 (7)	O1B—N4B—O2B	124.56 (7)
O1A—N4A—C2A	118.18 (6)	O1B—N4B—C2B	118.56 (7)
O2A—N4A—C2A	116.70 (7)	O2B—N4B—C2B	116.86 (6)
N1A—C1A—N2A	110.12 (7)	N1B—C1B—N2B	110.33 (7)
N1A—C1A—H1AA	124.9	N1B—C1B—H1BA	124.8
N2A—C1A—H1AA	124.9	N2B—C1B—H1BA	124.8
N3A—C2A—N1A	117.27 (7)	N3B—C2B—N1B	117.63 (7)
N3A—C2A—N4A	121.04 (7)	N3B—C2B—N4B	121.29 (7)
N1A—C2A—N4A	121.66 (6)	N1B—C2B—N4B	121.08 (7)
C1A—N2A—N3A—C2A	−0.05 (8)	C1B—N2B—N3B—C2B	0.10 (9)
C2A—N1A—C1A—N2A	−0.45 (9)	C2B—N1B—C1B—N2B	−0.54 (9)
N3A—N2A—C1A—N1A	0.33 (10)	N3B—N2B—C1B—N1B	0.30 (10)
N2A—N3A—C2A—N1A	−0.27 (9)	N2B—N3B—C2B—N1B	−0.49 (9)
N2A—N3A—C2A—N4A	−178.46 (7)	N2B—N3B—C2B—N4B	179.31 (7)
C1A—N1A—C2A—N3A	0.46 (9)	C1B—N1B—C2B—N3B	0.66 (9)
C1A—N1A—C2A—N4A	178.64 (7)	C1B—N1B—C2B—N4B	−179.14 (7)
O1A—N4A—C2A—N3A	−5.31 (11)	O1B—N4B—C2B—N3B	4.58 (12)
O2A—N4A—C2A—N3A	173.84 (7)	O2B—N4B—C2B—N3B	−176.50 (8)
O1A—N4A—C2A—N1A	176.57 (7)	O1B—N4B—C2B—N1B	−175.62 (8)
O2A—N4A—C2A—N1A	−4.27 (11)	O2B—N4B—C2B—N1B	3.29 (11)

D—H···A	D—H	H···A	D···A	D—H···A
N2A—H1N1···N1Ai	0.885 (15)	1.995 (15)	2.8540 (9)	163.4 (15)
N2B—H1N2···N1Bii	0.857 (16)	2.057 (16)	2.9128 (10)	176.0 (16)
C1A—H1AA···O2Aiii	0.93	2.50	3.1129 (10)	124.
C1B—H1BA···O2Bii	0.93	2.51	3.0451 (11)	117.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2A—H1N1⋯N1Ai	0.885 (15)	1.995 (15)	2.8540 (9)	163.4 (15)
N2B—H1N2⋯N1Bii	0.857 (16)	2.057 (16)	2.9128 (10)	176.0 (16)
C1A—H1AA⋯O2Aiii	0.93	2.50	3.1129 (10)	124
C1B—H1BA⋯O2Bii	0.93	2.51	3.0451 (11)	117

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