1-[2-(2,6-Dichloro­benz­yloxy)-2-(2-fur­yl)eth­yl]-1H-1,2,4-triazole

Özden Özel Güven; Hakan Tahtacı; Simon J Coles; Tuncer Hökelek

doi:10.1107/S1600536809052568

. 2009 Dec 12;66(Pt 1):o107–o108. doi: 10.1107/S1600536809052568

1-[2-(2,6-Dichlorobenzyloxy)-2-(2-furyl)ethyl]-1H-1,2,4-triazole

Özden Özel Güven ^a, Hakan Tahtacı ^a, Simon J Coles ^b, Tuncer Hökelek ^c,^*

PMCID: PMC2980028 PMID: 21579997

Abstract

In the molecule of the title compound, C₁₅H₁₃Cl₂N₃O₂, the triazole ring is oriented at dihedral angles of 2.54 (13) and 44.43 (12)°, respectively with respect to the furan and dichlorobenzene rings. The dihedral angle between the dichlorobenzene and furan rings is 46.75 (12)°. In the crystal structure, intermolecular C—H⋯O hydrogen bonds link the molecules into centrosymmetric dimers and π–π contacts between dichlorobenzene rings [centroid–centroid distance = 3.583 (2) Å] may further stabilize the structure. Intermolecular C—H⋯π contacts between the triazole and furan rings also occur.

Related literature

For general background to antifungal agents, see: Caira et al. (2004 ▶); Godefroi et al. (1969 ▶); Özel Güven et al. (2007a ▶,b ▶); Paulvannan et al. (2001 ▶); Peeters et al. (1996 ▶); Wahbi et al. (1995 ▶). For related structures, see: Freer et al. (1986 ▶); Özel Güven et al. (2008a ▶,b ▶,c ▶,d ▶,e ▶,f ▶); Özel Güven et al. (2009 ▶); Peeters et al. (1979 ▶).

Experimental

Crystal data

C₁₅H₁₃Cl₂N₃O₂
M _r = 338.18
Monoclinic,
a = 10.5853 (3) Å
b = 12.4960 (2) Å
c = 12.5850 (3) Å
β = 114.455 (1)°
V = 1515.32 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.44 mm⁻¹
T = 120 K
0.40 × 0.40 × 0.10 mm

Data collection

Bruker–Nonius KappaCCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2007 ▶) T _min = 0.837, T _max = 0.955
33067 measured reflections
3438 independent reflections
2775 reflections with I > 2σ(I)
R _int = 0.058

Refinement

R[F ² > 2σ(F ²)] = 0.067
wR(F ²) = 0.180
S = 1.04
3438 reflections
200 parameters
H-atom parameters constrained
Δρ_max = 1.20 e Å⁻³
Δρ_min = −0.76 e Å⁻³

Data collection: COLLECT (Nonius, 1998 ▶); cell refinement: DENZO (Otwinowski & Minor, 1997 ▶) and COLLECT; data reduction: DENZO and COLLECT; 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 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809052568/xu2704sup1.cif

e-66-0o107-sup1.cif^{(18.6KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809052568/xu2704Isup2.hkl

e-66-0o107-Isup2.hkl^{(165.2KB, 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
C2—H2⋯O1ⁱ	0.93	2.44	3.363 (3)	173
C9—H9B⋯Cl2	0.97	2.62	3.109 (3)	112
C1—H1⋯Cg2ⁱⁱ	0.93	2.79	3.488 (4)	133
C7—H7⋯Cg1ⁱⁱⁱ	0.93	2.93	3.570 (4)	127

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Symmetry codes: (i) Inline graphic ; (ii) ; (iii) . Cg1 and Cg2 are the centroids of the N1–N3/C1/C2 and O2/C5–C8 rings, respectively.

Acknowledgments

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

supplementary crystallographic information

Comment

In recent years, among antifungal agents, azole derivatives still have an important place in the class of systemic antifungal drugs. Some ether structures containing 1H-imidazole ring like micozanole, ecozanole and sulconazole have been synthesized and developed for clinical uses as antifungal agents (Godefroi et al., 1969). The crystal structures of these ether derivatives like miconazole (Peeters et al., 1979), econazole (Freer et al., 1986) have been reported previously. Also, antifungal activity of aromatic ethers possessing 1H-1,2,4-triazole ring have been reported (Wahbi et al., 1995). Itraconazole (Peeters et al., 1996) and fluconazole (Caira et al., 2004) are 1H-1,2,4-triazole ring containing azole derivatives. 1,2,4-Triazoles are biologically interesting molecules and their chemistry is receiving considerable attention due to antihypertensive, antifungal and antibacterial properties (Paulvannan et al., 2001). Ether structures possessing 1H-benzimidazole ring have been reported to show antibacterial activity more than antifungal activity (Özel Güven et al., 2007a,b). 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 derivatives have been reported recently (Özel Güven et al., 2008e,f; Özel Güven et al., 2009). Now, we report herein the crystal structure of 2,6-dichloro- derivative of 1H-1,2,4-triazole and furyl rings containing 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 furan and dichlorobenzene rings at dihedral angles of 2.54 (13)° and 44.43 (12)°, respectively. Atoms C3, C4 and C9 are -0.064 (3), 0.039 (3) and -0.073 (3) Å away from the planes of the triazole, furan and dichlorobenzene, respectively. So, they are nearly coplanar with the adjacent rings. The dichlorobenzene ring is oriented with respect to the furan ring at a dihedral angle of 46.75 (12)°. An intramolecular C—H···Cl hydrogen bond (Table 1) results in the formation of a five-membered ring (Cl2/H9B/C9/C10/C15) adopting envelope conformation with H9B atom displaced by 0.210 (1) Å from the plane of the other ring atoms.

In the crystal structure, intermolecular C-H···O hydrogen bonds (Table 1) link the molecules into centrosymmetric dimers (Fig. 2), in which they may be effective in the stabilization of the structure. The π–π contact between the dichlorobenzene rings, Cg3—Cg3ⁱ [symmetry code: (i) -x, -y, 1 - z, where Cg3 is centroid of the ring (C10-C15)] may further stabilize the structure, with centroid-centroid distance of 3.583 (2) Å. Intermolecular C—H···π interactions (Table 1) are also observed between the triazole and furan rings.

Experimental

The title compound was synthesized by the reaction of 1-(furan-2-yl)-2-(1H-1,2,4-triazol-1-yl)ethanol (unpublished results) with NaH and appropriate benzyl halide. To a solution of alcohol (500 mg, 2.791 mmol) in DMF (4 ml) was added NaH (112 mg, 2.791 mmol) in small fractions. The appropriate benzyl halide (669 mg, 2.791 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 suitable for X-ray analysis were obtained by the recrystallization of the ether from isopropanol solution (yield; 500 mg, 53%).