1-(4-Nitro­phenoxy­meth­yl)-1H-1,2,4-triazole

Jian Li

doi:10.1107/S1600536807060758

. 2007 Dec 6;64(Pt 1):o17. doi: 10.1107/S1600536807060758

1-(4-Nitrophenoxymethyl)-1H-1,2,4-triazole

Jian Li ^a,^*

PMCID: PMC2914979 PMID: 21200735

Abstract

The asymmetric unit of the title compound, C₉H₈N₄O₃, contains two independent molecules. The dihedral angles formed by the triazole and benzene rings in the two independent molecules are 83.3 (3) and 86.9 (4)°. The molecular packing involves weak C—H⋯N and C—H⋯O interactions, and π–π stacking interactions [centroid-to-centroid distance 3.745 (1) Å] between the aromatic rings of pairs of molecules.

Related literature

For the synthesis of related energetic polynitro and heterocyclic compounds, see: Jin et al. (2005 ▶, 2006 ▶); Wang et al. (2007 ▶).

Experimental

Crystal data

C₉H₈N₄O₃
M _r = 220.19
Monoclinic,
a = 11.2344 (4) Å
b = 7.7197 (3) Å
c = 22.789 (1) Å
β = 94.730 (1)°
V = 1969.65 (14) Å³
Z = 8
Mo Kα radiation
μ = 0.12 mm⁻¹
T = 296 (2) K
0.20 × 0.10 × 0.10 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.977, T _max = 0.989
18061 measured reflections
3863 independent reflections
2540 reflections with I > 2σ(I)
R _int = 0.056

Refinement

R[F ² > 2σ(F ²)] = 0.053
wR(F ²) = 0.134
S = 1.07
3863 reflections
290 parameters
H-atom parameters constrained
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.17 e Å⁻³

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT-Plus (Bruker, 2001 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997 ▶); molecular graphics: SHELXTL (Bruker, 2001 ▶); software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536807060758/ln2005sup1.cif

e-64-00o17-sup1.cif^{(20.3KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807060758/ln2005Isup2.hkl

e-64-00o17-Isup2.hkl^{(189.4KB, hkl)}

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

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5⋯O1ⁱ	0.93	2.59	3.367 (3)	141
C14—H14⋯O3ⁱ	0.93	2.41	3.249 (3)	150
C17—H17⋯N4ⁱⁱ	0.93	2.56	3.351 (3)	144

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Symmetry codes: (i) Inline graphic ; (ii) .

Acknowledgments

The author gratefully acknowledges the financial support of the National Science Funds for Distinguished Young Scholars Program and Hubei Provincial Department of Education, People’s Republic of China.

supplementary crystallographic information

Comment

The derivatives of 1,2,4-triazole are of great significance as pharmaceuticals, pesticides and high energetic materials. In recent years, the synthesis of energetic, polynitro and heterocyclic compounds have attracted considerable interest (Wang et al., 2007; Jin et al., 2005, 2006). This paper reports the crystal structure of the title 1,3,4-triazole derivative, (I).

The asymmetric unit of the title compound contains two independent molecules (Fig. 1). The dihedral angles formed by the triazole and benzene rings in the two independent molecules are 83.3 (3)° and 86.9 (4)°, respectively. The molecular packing involves weak C—H···N and C—H···O interactions (Table 1), and π···π stacking interactions of aromatic rings with the centroid to centroid distance being 3.745 (1) Å for adjacent benzene rings in pairs of molecules.

Experimental

Anhydrous K₂CO₃(420 mg, 3.0 mmol) was added to a solution of p-nitrophenol (139 mg, 1.0 mmol) in anhydrous acetonitrile (30 ml). After stirring for 30 min at 333 K, 1-chloromethyl-1H-1, 2, 4-triazole (117 mg, 1.0 mmol) was added. The mixture was refluxed for 12 h. After cooling, a small amount of precipitate was removed by filtration. The residue was purified by column chromatography to obtain a white solid (yield 86.2%, m.p. 465 K decomp.). Suitable crystals were obtained by evaporation of an ethyl acetate solution of the product.