(1H-1,2,4-Triazol-1-yl)methyl 2-(2,4-dichloro­phen­oxy)acetate

Yun-Man Xie; Yu-Min Li

doi:10.1107/S1600536810012456

. 2010 Apr 21;66(Pt 5):o1122. doi: 10.1107/S1600536810012456

(1H-1,2,4-Triazol-1-yl)methyl 2-(2,4-dichlorophenoxy)acetate

Yun-Man Xie ^a,^*, Yu-Min Li ^a

PMCID: PMC2979088 PMID: 21579172

Abstract

In the title compound, C₁₁H₉Cl₂N₃O₃, the triazole and benzene rings are roughly parallel to one another [dihedral angle = 4.99 (2)°] because the C—O—C—C—O chain that links the two rings is folded [O—C—C—O = 8.60 (2)°] rather than fully extended. In the crystal, weak intermolecular C—H⋯N and C—H⋯O interactions are present, and π–π interactions are indicated by the short distances [3.749 (3) Å] between the centroids of the triazole and benzene rings.

Related literature

For details of the biological activities of triazole-containing compounds, see: Xu et al. (2002 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C₁₁H₉Cl₂N₃O₃
M _r = 302.11
Monoclinic,
a = 10.814 (2) Å
b = 6.4514 (13) Å
c = 18.698 (4) Å
β = 101.05 (3)°
V = 1280.2 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.51 mm⁻¹
T = 293 K
0.74 × 0.22 × 0.05 mm

Data collection

Rigaku R-AXIS RAPID IP area-detector diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T _min = 0.702, T _max = 0.976
2253 measured reflections
2253 independent reflections
1816 reflections with I > 2σ(I)
R _int = 0.000

Refinement

R[F ² > 2σ(F ²)] = 0.036
wR(F ²) = 0.096
S = 1.02
2253 reflections
172 parameters
H-atom parameters constrained
Δρ_max = 0.24 e Å⁻³
Δρ_min = −0.34 e Å⁻³

Data collection: RAPID-AUTO (Rigaku, 2004 ▶); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; 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.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810012456/hg2669sup1.cif

e-66-o1122-sup1.cif^{(16.7KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810012456/hg2669Isup2.hkl

e-66-o1122-Isup2.hkl^{(110.8KB, hkl)}

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

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

Cg1 and Cg2 are the centroids of the triazole ring (C10/C11/N1–N3) and the benzene ring (C1–C6), respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6A⋯N3ⁱ	0.93	2.45	3.353 (3)	164
C7—H7B⋯O1ⁱⁱ	0.97	2.58	3.390 (2)	142
C9—H9A⋯O2ⁱⁱⁱ	0.97	2.52	3.381 (3)	148
C11—H11A⋯O2ⁱⁱⁱ	0.93	2.54	3.293 (2)	139
Cg1⋯Cg2ⁱ			3.665 (2)

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

supplementary crystallographic information

Comment

Compounds containing the triazole ring system are well known as efficient fungicides in agriculture, where they act by inhibiting the biosynthesis of ergosterol (Xu et al., 2002). In order to search for new triazole compounds with higher bioactivity, the title compound was synthesized and its structure is reported here.

In title compound, all bond lengths in the molecular are normal (Allen et al., 1987). Triazole ring (C10/C11/N1—N3) and benzene ring (C1—C6) are essentially parallel to one another (dihedral angle of 4.99 (2)°) because the C—O—C—C—O chain that links the two rings is folded [O—C—C—O torsion angle = 8.60 (2)°] rather than fully extended. π—π interactions are indicated by the short distance (Cg1···Cg1 distance of 3.749 (3) Å, symmetry code: 1-x,-y,-z) between the centroids of the triazole rings (C10/C11/N1—N3) (Cg1) and benzene rings C1—C6 (Cg2) (Table 1). There are weaker C—H···N, C—H···O intermolecular interactions, which stabilized the structure (Table 1).

Experimental

To a 100 ml flask were added 10 mmol of (1H-1,2,4-triazol-1-yl)methanol and 11 mmol of triethylamine in 20 ml of dryed acetone, to which 10 mmol of 2-(2,4-dichlorophenoxy)acetyl chloride in 10 ml of acetone was then dropwise added with stirring on ice-cold water bath within 0.5 h. The reaction took place immediately, and a lot of white solid appeared. The mixture was heated and refluxed for 2 h, and then cooled to room temperature. After filtering and distilling in reduced pressure, a crude product was obtained and purified by flash column chromatography (silicagel, using ethyl ethanoate: cyclohexane = 1:3 as eluent) to afford the title compound. Single crystals suitable for X-ray measurements were obtained by recrystallization from ethyl acetate at room temperature.