N-(1H-1,2,4-Triazol-5-yl)pyridine-2-carboxamide

Jing Miao; Maomao Jia; Xianlin Liu; Wei Xiong; Zilu Chen

doi:10.1107/S1600536809041269

. 2009 Oct 17;65(Pt 11):o2738. doi: 10.1107/S1600536809041269

N-(1H-1,2,4-Triazol-5-yl)pyridine-2-carboxamide

Jing Miao ^a, Maomao Jia ^a, Xianlin Liu ^a, Wei Xiong ^a, Zilu Chen ^a,^*

PMCID: PMC2970976 PMID: 21578333

Abstract

In the structure of the title compound, C₈H₇N₅O, the pyridine ring and the imidazole ring are nearly coplanar, making a dihedral angle of 2.97 (15)°. An intramolecular N—H⋯O hydrogen bond occurs. In the crystal molecules are connected by intermolecular hydrogen bonds and π–π stacking interactions between neighboring imidazole rings [centroid–centroid distance = 3.5842 (5) Å and off-set angle = 21.77°], leading to the formation of a two-dimensional supramolecular sheet.

Related literature

For an alternative preparative method for the title compound, see: Browne & Polya (1968 ▶). For the potential bioinorganic applications of 1,2,4-triazole derivatives, see: Bohm & Karow (1981 ▶); Bahel et al. (1984 ▶).

Experimental

Crystal data

C₈H₇N₅O
M _r = 189.19
Monoclinic,
a = 8.6906 (17) Å
b = 5.2854 (10) Å
c = 17.880 (4) Å
β = 90.700 (3)°
V = 821.2 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 273 K
0.26 × 0.24 × 0.18 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 1998 ▶) T _min = 0.972, T _max = 0.980
3938 measured reflections
1443 independent reflections
961 reflections with I > 2σ(I)
R _int = 0.095

Refinement

R[F ² > 2σ(F ²)] = 0.046
wR(F ²) = 0.106
S = 1.00
1443 reflections
128 parameters
H-atom parameters constrained
Δρ_max = 0.17 e Å⁻³
Δρ_min = −0.16 e Å⁻³

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; 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.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809041269/ez2185sup1.cif

e-65-o2738-sup1.cif^{(15.6KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809041269/ez2185Isup2.hkl

e-65-o2738-Isup2.hkl^{(71.2KB, 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
N2—H21⋯N3ⁱ	0.88	2.09	2.946 (2)	164
N4—H41⋯O1ⁱⁱ	0.86	2.06	2.873 (2)	158
N4—H41⋯O1	0.86	2.17	2.629 (2)	113

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

Acknowledgments

We gratefully acknowledge the financial support of the Guangxi Natural Science Foundation (No. 0991008) and the Innovation Project of Guangxi Graduate Education (2009106020703M43), China.

supplementary crystallographic information

Comment

1,2,4-Triazoles derivatives represent an interesting class of heterocycles. They present various potential applications in bioinorganic chemistry (Bohm & Karow, 1981; Bahel, et al., 1984). The preparation of the title compound has been reported previously (Browne & Polya, 1968), but its crystal structure has not yet been reported. Thus we report here the structure (Fig. 1) of the title compound obtained using an alternative method.

The pyridine ring and the imidazole ring are nearly co-planar with a dihedral angle of 2.97 (15)°. An intramolecular N—H···O hydrogen bond is present in the molecule. Adjacent molecules are connected alternatively by intermolecular N—H···N and N—H···O hydrogen bonds into one dimensional supramolecular chains (Fig. 2). The neighboring imidazole rings from adjacent one dimensional chains are parallel to each other with a perpendicular distance of 3.3285 (1) Å, a centroid-to-centroid distance of 3.5842 (5) Å and an off-set angle of 21.774° (calculated as the angle formed by the line through the two centroids of the two imidazole rings and the normal of the imidazole plane). This indicates the presence of a π–π stacking interaction between the neighboring imidazole rings from adjacent one dimensional chains, which leads to the construction of a two dimensional supramolecular sheet (Fig. 2).

Experimental

A mixture of 1,2-di-2-pyridyl-ethane-dione (0.2122 g, 1 mmol), 5-amino-1,2,4-triazole (0.1682 g, 2 mmol) and methanol (20 ml) was refluxed at 343 K for three hours. It was then filtered and the filtrate was left at ambient temperature to evaporate for three days, yielding crystals of the product. The overall yield is 70%. Elemental analysis for C₈H₇N₅, calculated: C 55.48, H 4.07, N 40.44%; found: C 55.12, H 4.35, N 40.82%.