N′-(4-Methoxy­benzo­yl)pyridine-2-carbohydrazide

Hai Zhang; Zuoxiang Wang; Yan Liu

doi:10.1107/S1600536810013437

. 2010 Apr 24;66(Pt 5):o1145. doi: 10.1107/S1600536810013437

N′-(4-Methoxybenzoyl)pyridine-2-carbohydrazide

Hai Zhang ^a, Zuoxiang Wang ^a,^*, Yan Liu ^a

PMCID: PMC2979049 PMID: 21579193

Abstract

The crystal structure of the title compound, C₁₄H₁₃N₃O₃, exhibits two intermolecular N—H⋯O hydrogen bonds.

Related literature

For general background to the coordination chemistry of pyridine derivatives, see: Koningsbruggen et al. (1997 ▶); Klingele & Brooker (2003 ▶); Suksrichavalit et al. (2009 ▶). For their biological activity, see: Tozkoparan et al. (2000 ▶); Grénman et al. (2003 ▶); Alagarsamy et al. (2008 ▶); Isloor et al. (2009 ▶). For their syntheses, see: Klingsberg (1958 ▶); Potts (1961 ▶).

Experimental

Crystal data

C₁₄H₁₃N₃O₃
M _r = 271.27
Monoclinic,
a = 14.836 (3) Å
b = 11.6078 (17) Å
c = 7.6499 (12) Å
β = 97.137 (11)°
V = 1307.2 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 293 K
0.25 × 0.20 × 0.18 mm

Data collection

Rigaku SCXmini diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T _min = 0.976, T _max = 0.982
13109 measured reflections
2957 independent reflections
1909 reflections with I > 2σ(I)
R _int = 0.053

Refinement

R[F ² > 2σ(F ²)] = 0.053
wR(F ²) = 0.143
S = 1.02
2957 reflections
183 parameters
H-atom parameters constrained
Δρ_max = 0.16 e Å⁻³
Δρ_min = −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 (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810013437/om2329sup1.cif

e-66-o1145-sup1.cif^{(15.9KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810013437/om2329Isup2.hkl

e-66-o1145-Isup2.hkl^{(145.1KB, 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
N1—H1A⋯O1ⁱ	0.85	2.11	2.9479 (19)	168
N2—H2A⋯O2ⁱⁱ	0.85	2.13	2.938 (2)	159

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

Acknowledgments

We are grateful to the Jingye Pharmochemical Pilot Plant for financial assistance though project 8507041056.

supplementary crystallographic information

Comment

As the 1,2,4-triazole ring possesses strong electron donors, the coordination chemistry of 1,2,4-triazole derivatives has gained a great deal of attention in recent years (Koningsbruggen et al., 1997; Klingele & Brooker 2003; Suksrichavalit et al., 2009). Some 1,2,4-triazole compounds have biological activity (Tozkoparan et al., 2000; Grénman et al., 2003; Alagarsamy et al., 2008; Isloor et al., 2009). We report here the crystal structure of the title compound, which can be used to synthesize 3(or 5)-(2-pyridyl)-1,2,4-triazole derivatives (Klingsberg, 1958; Potts, 1961).

The stucture of the title compound is shown in Fig. 1. The structure displays two N—H···O intermolecular hydrogen bonds.

Experimental

The title compound was prepared by the reaction of 2-picolinyl hydrazide (2.75 g, 20 mmol) with 4-methoxybenzoyl chloride (3.5 g, 20 mmol) in 30 ml N,N-dimethylacetamide at room temperature. The colorless product was collected by recrystallization from ethanol, and the single crystals suitable for X-ray diffraction were selected.