(1-Phenyl-1H-1,2,3-triazol-4-yl)methyl pyridine-3-carboxyl­ate

Zakirjon Karimov; Ibrakhim Abdugafurov; Samat Talipov; Bakhodir Tashkhodjaev

doi:10.1107/S1600536810021999

. 2010 Jun 16;66(Pt 7):o1674. doi: 10.1107/S1600536810021999

(1-Phenyl-1H-1,2,3-triazol-4-yl)methyl pyridine-3-carboxylate

Zakirjon Karimov ^a,^*, Ibrakhim Abdugafurov ^b, Samat Talipov ^c, Bakhodir Tashkhodjaev ^d

PMCID: PMC3007003 PMID: 21587899

Abstract

In the title compound, C₁₅H₁₂N₄O₂, the dihedral angle between the planes of the nicotinoyloxy fragment and triazole ring is 88.61 (5)°. The dihedral angle between the planes of triazole and benzene rings is 16.54 (11)°. The crystal structure is stabilized by intermolecular C—H⋯N, C—H⋯O and C—H⋯π(triazole) hydrogen bonds and aromatic π–π stacking interactions between the benzene and triazole rings [centroid–centroid distance = 3.895 (1) Å]

Related literature

For the synthesis of 1,2,3-triazole derivatives, see: Berestovitskaya et al. (2007 ▶); Piterskaya et al. (1996a ▶,b ▶). For their physiological activity, see: Contreras et al. (1978 ▶). For related structures, see: Berestovitskaya et al. (2007 ▶); Monkowius et al. (2007 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C₁₅H₁₂N₄O₂
M _r = 280.29
Monoclinic,
a = 5.5178 (5) Å
b = 23.650 (2) Å
c = 10.287 (2) Å
β = 91.841 (14)°
V = 1341.8 (3) Å³
Z = 4
Cu Kα radiation
μ = 0.79 mm⁻¹
T = 293 K
0.70 × 0.45 × 0.10 mm

Data collection

Oxford Diffraction Xcalibur Ruby diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009 ▶) T _min = 0.674, T _max = 1.000
4791 measured reflections
2460 independent reflections
1877 reflections with I > 2σ(I)
R _int = 0.026

Refinement

R[F ² > 2σ(F ²)] = 0.041
wR(F ²) = 0.124
S = 1.04
2460 reflections
191 parameters
H-atom parameters constrained
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.13 e Å⁻³

Data collection: CrysAlis PRO (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: XP in SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810021999/kp2262sup1.cif

e-66-o1674-sup1.cif^{(18.5KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810021999/kp2262Isup2.hkl

e-66-o1674-Isup2.hkl^{(120.9KB, hkl)}

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

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

Cg1 is the centroid of the triazole ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C14—H14⋯N1ⁱ	0.93	2.64	3.550 (3)	165
C2—H2⋯O1ⁱⁱ	0.93	2.71	3.464 (2)	139
C15—H15⋯O1ⁱⁱⁱ	0.93	2.68	3.559 (2)	158
C7—H7a⋯Cg1^iv	0.97	2.92	3.313 (2)	106

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

Acknowledgments

Tashkent Institute of Irrigation and Melioration is thanked for support.

supplementary crystallographic information

Comment

Triazole derivatives possess different biological activities (Contreras et al. 1978). The title compound was synthesized with purpose of finding of a potential biological active compound.

The asymmetric unit contains one molecule of 1-phenyl-4-(nicotinoyloxymethyl)-1,2,3-triazole (Fig. 1). In the molecule nicotinoyloxy, phenyl groups and triazole system are planar, with r.m.s. deviations of 0.0075, 0.0048 and 0.0028 Å, respectively. Nicotinoyloxy fragment arranged nearly perpendicular to triazole ring. The angle between the planes of the nicotinoyloxy fragment and triazole ring is 88.61 (5)°. The angle between the planes of triazole and benzene rings is 16.54 (11)°. The observed structure is stabilized by C—H···N, C—H···O and C—H···π (triazole) type hydrogen bonds (Table 1) and aromatic π–π stacking interactions. A centrosymmetric π–π stacking interactions are observed between triazole group and benzene group of molecules at x,y,z and 1 - x, -y, 2 - z where the ring-centroid separation is 3.895 (1) Å, triazole centroid distance to benzene plane is 3.429 (1) Å with ring offset of 1.847 (1) Å (Fig. 2). The bond distances and angles in molecule are in normal ranges (Allen et al., 1987).

Experimental

Mixture of 3-(nicotinoyloxy)-1-propyne (1.61 g, 0,01 mole) and fresh prepared phenylazide (1.310 g, 0,011 mole) in 30 ml toluen was heated with a backflow condenser for 6 h. Then it was cooled and precipitate were isolated by decantation. Obtained crystals were washed with ether and re-crystallized from toluen. It was obtained 78.3% yeild (2.19 g) of title compound, m.p. 96–97° C, R_f =0.53 (ether-hexane 9:1). Colorless crystals suitable for X-ray analysis were obtained from acetone by slow evaporation.