1-[2-(2,4-Dichloro­benz­yloxy)-2-phenyl­ethyl]-1H-1,2,4-triazole

Özden Özel Güven; Hakan Tahtacı; M Nawaz Tahir; Tuncer Hökelek

doi:10.1107/S1600536808039196

. 2008 Nov 29;64(Pt 12):o2465. doi: 10.1107/S1600536808039196

1-[2-(2,4-Dichlorobenzyloxy)-2-phenylethyl]-1H-1,2,4-triazole

Özden Özel Güven ^a, Hakan Tahtacı ^a, M Nawaz Tahir ^b, Tuncer Hökelek ^c,^*

PMCID: PMC2959862 PMID: 21581433

Abstract

In the molecule of the title compound, C₁₇H₁₅Cl₂N₃O, the triazole ring is oriented at dihedral angles of 9.24 (6) and 82.49 (6)°, respectively, with respect to the phenyl and dichlorobenzene rings. The dihedral angle between the dichlorobenzene and phenyl rings is 88.57 (5)°. An intramolecular C—H⋯O contact results in the formation of a planar five-membered ring.

Related literature

For general backgroud, see: Paulvannan et al. (2001 ▶); Godefroi et al. (1969 ▶); Özel Güven et al. (2007a ▶,b ▶); Wahbi et al. (1995 ▶). For related structures, see: Peeters et al. (1979 ▶); Freer et al. (1986 ▶); Özel Güven et al. (2008a ▶,b ▶,c ▶,d ▶,e ▶,f ▶).

Experimental

Crystal data

C₁₇H₁₅Cl₂N₃O
M _r = 348.22
Monoclinic,
a = 10.5630 (3) Å
b = 13.7933 (5) Å
c = 11.4437 (4) Å
β = 101.840 (2)°
V = 1631.86 (10) Å³
Z = 4
Mo Kα radiation
μ = 0.41 mm⁻¹
T = 296 (2) K
0.35 × 0.25 × 0.15 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T _min = 0.871, T _max = 0.942
17794 measured reflections
4055 independent reflections
3135 reflections with I > 2σ(I)
R _int = 0.026

Refinement

R[F ² > 2σ(F ²)] = 0.037
wR(F ²) = 0.104
S = 1.04
4055 reflections
208 parameters
H-atom parameters constrained
Δρ_max = 0.32 e Å⁻³
Δρ_min = −0.24 e Å⁻³

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808039196/su2082sup1.cif

e-64-o2465-sup1.cif^{(18.8KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808039196/su2082Isup2.hkl

e-64-o2465-Isup2.hkl^{(113.2KB, 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
C13—H13⋯O1	0.93	2.37	2.7191 (18)	102

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Symmetry code: (i) Inline graphic .

Acknowledgments

The authors acknowledge the Zonguldak Karaelmas University Research Fund (Project No. 2008–13–02–06) for financial support.

supplementary crystallographic information

Comment

1,2,4-Triazoles are biologically interesting molecules and their chemistry is receiving considerable attention due to their antihypertensive, antifungal and antibacterial properties (Paulvannan et al., 2001). Some ether structures containing the 1H-imidazole ring, like miconazole, econazole and sulconazole, have been synthesized and developed for clinical use as antifungal agents (Godefroi et al., 1969). Also, antifungal activity of aromatic ethers possessing a 1H-1,2,4-triazole ring have been reported (Wahbi et al., 1995). However, similar ether structures possessing a 1H-benzimidazole ring have been reported to show antibacterial activity more than antifungal activity (Özel Güven et al., 2007a,b). The crystal structures of these ether derivatives, such as miconazole (Peeters et al., 1979) and econazole (Freer et al., 1986), have been reported. The crystal structures of 1H-benzimidazole ring containing ether derivatives (Özel Güven et al., 2008a,b,c,d) and also, 1H-1,2,4-triazole ring containing ether derivative have been reported recently (Özel Güven et al., 2008e). Here we report on the crystal structure of the 2,4-dichloro derivative of a 1H-1,2,4-triazole ring compound containing an ether structure.

In the molecule of the title compound (Fig. 1) the bond lengths and angles are generally within normal ranges. The planar triazole ring is oriented with respect to the phenyl and dichlorobenzene rings at dihedral angles of 9.24 (6)° and 82.49 (6)°, respectively. The dichlorobenzene ring is oriented with respect to the phenyl ring at a dihedral angle of 88.57 (5)°. The intramolecular C—H···O contact results in the formation of a planar five-membered ring (O1/H13/C11—C13), which is oriented with respect to dichlorobenzene ring at a dihedral angle of 0.65 (4)°, hence they are coplanar.

In the crystal structure of the title compound, the molecules stack along the c direction (Fig. 2). There is a weak intermolecular C—H···π contact between the methylene group and the dichlorobenzene ring [Table 1; where Cg3 is the centroid of the ring (C12-C17)].

Experimental

The title compound was synthesized by the reaction of 1-phenyl-2-(1H-1,2,4 -triazol-1-yl)ethanol (Özel Güven et al., 2008f) with NaH and the appropriate benzyl halide. To the solution of the alcohol (300 mg, 1.586 mmol) in DMF (4 ml) was added NaH (63 mg, 1.586 mmol) in small fractions. The appropriate benzyl halide (310 mg, 1.586 mmol) was added dropwise. The mixture was stirred at room temperature for 3 h, and excess hydride was decomposed with methyl alcohol (5 ml). After evaporation to dryness under reduced pressure, the crude residue was suspended with water and extracted with methylene chloride. The organic layer was dried over anhydrous sodium sulfate and then evaporated to dryness. The crude residue was purified by chromatography on a silica-gel column using chloroform as eluent. Crystals of the title compound, suitable for X-ray analysis, were obtained by recrystallization of the ether from 2-propanol (yield; 365 mg, 66%).