1-{2-Phenyl-2-[4-(trifluoro­meth­yl)­benzyl­oxy]eth­yl}-1H-benzimidazole

Özden Özel Güven; Taner Erdoğan; Simon J Coles; Tuncer Hökelek

doi:10.1107/S1600536808024033

. 2008 Jul 31;64(Pt 8):o1655–o1656. doi: 10.1107/S1600536808024033

1-{2-Phenyl-2-[4-(trifluoromethyl)benzyloxy]ethyl}-1H-benzimidazole

Özden Özel Güven ^a, Taner Erdoğan ^a, Simon J Coles ^b, Tuncer Hökelek ^c,^*

PMCID: PMC2962243 PMID: 21203341

Abstract

The asymmetric unit of the crystal structure of the title compound, C₂₃H₁₉F₃N₂O, contains two independent molecules. In the two molecules the planar benzimidazole ring systems are oriented with respect to the phenyl/trifluoromethylbenzene rings at dihedral angles of 9.62 (6)/78.63 (7) and 2.53 (8)/83.83 (9)°. In the crystal structure, intermolecular C—H⋯N hydrogen bonds link the molecules into R ₂ ²(6) dimers. The molecules are elongated along [001] and stacked along the b axis.

Related literature

For general background, see: Brammer & Feczko (1988 ▶); Özel Güven et al. (2007a ▶,b ▶). For related literature, see: Song & Shin (1998 ▶); Freer et al. (1986 ▶); Peeters et al. (1996 ▶, 1979a ▶,b ▶); Caira et al. (2004 ▶); Özel Güven et al. (2008a ▶,b ▶). For ring motif details, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C₂₃H₁₉F₃N₂O
M _r = 396.40
Monoclinic,
a = 39.3006 (15) Å
b = 9.5834 (2) Å
c = 23.0120 (9) Å
β = 113.668 (1)°
V = 7938.1 (5) Å³
Z = 16
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 120 (2) K
0.35 × 0.2 × 0.14 mm

Data collection

Bruker Nonius KappaCCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2007 ▶) T _min = 0.974, T _max = 0.984
28014 measured reflections
8735 independent reflections
5066 reflections with I > 2σ(I)
R _int = 0.072

Refinement

R[F ² > 2σ(F ²)] = 0.081
wR(F ²) = 0.227
S = 1.06
8735 reflections
524 parameters
H-atom parameters constrained
Δρ_max = 0.62 e Å⁻³
Δρ_min = −0.59 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 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808024033/xu2445sup1.cif

e-64-o1655-sup1.cif^{(32.8KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808024033/xu2445Isup2.hkl

e-64-o1655-Isup2.hkl^{(275.1KB, 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
C1—H1⋯N2′ⁱ	0.93	2.45	3.210 (5)	139
C1′—H1′⋯N2ⁱⁱ	0.93	2.47	3.215 (5)	138

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

Acknowledgments

The authors acknowledge Zonguldak Karaelmas University Research Fund (grant No. 2004-13-02-16).

supplementary crystallographic information

Comment

In recent years, there has been increasing interest in synthesis of heterocyclic compounds having biological and commercial importances. Clotrimazole (Song & Shin, 1998), econazole (Freer et al., 1986), ketoconazole (Peeters et al., 1979a) and miconazole (Peeters et al., 1979b) are well known imidazole ring containing, while itraconazole (Peeters et al., 1996) and fluconazole (Caira et al., 2004) are 1H-1,2,4-triazole ring containing, azole derivatives. They have been developed for clinical uses as antifungal agents (Brammer & Feczko, 1988). Lately, similar structures to miconazole and econazole have been reported to show antibacterial activity more than antifungal activity (Özel Güven et al., 2007a,b). In these structures, benzimidazole ring has been found in place of the imidazole ring of miconazole and econazole. Recently, we reported the crystal structures of furyl (Özel Güven et al., 2008a) and phenyl (Özel Güven et al., 2008b) substituted compounds, and we report herein the crystal structure of title benzimidazole derivative.

The asymmetric unit of the crystal structure of the title compound (Fig. 1) contains two independent molecules, in which the bond lengths and angles are generally within normal ranges. The planar benzimidazole ring systems are oriented with respect to the phenyl and trifluoromethylbenzene rings at dihedral angles of 9.62 (6)°, 78.63 (7)° and 2.53 (8)°, 83.83 (9)° for unprimed and primed molecules, respectively. Atoms C8, C9, C16 and C8', C9', C16' are -0.102 (2), 0.093 (2), -0.008 (3) and 0.122 (3), -0.100 (3), -0.003 (3) Å away from the ring planes of the corresponding benzimidazole, phenyl and trifluoromethylbenzene, respectively. So, they are nearly coplanar with the attached rings. The trifluoromethylbenzene rings are oriented with respect to the phenyl rings at dihedral angles of 75.97 (9)° and 86.13 (9)° for unprimed and primed molecules, respectively.

In the crystal structure, intermolecular C—H···N hydrogen bonds (Table 1) link the molecules to form a R₂²(6) ring motif (Bernstein et al., 1995), in which they may be effective in the stabilization of the structure. The molecules are elongated along [001], and stacked along the b axis (Fig. 2).

Experimental

The title compound was synthesized by the reaction of 2-(1H-benzimidazol-1-yl)-1-phenylethanol (Özel Güven et al., 2007a) with NaH and appropriate benzyl halide. To the solution of alcohol (300 mg, 1.259 mmol) in DMF (2.4 ml) was added NaH (63 mg, 1.574 mmol) in small fractions. The appropriate benzyl halide (300 mg, 1.259 mmol) in DMF (1.2 ml) was added dropwise. The mixture was stirred at room temperature for 2 h and excess hydride was decomposed with a small amount of methyl alcohol. 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–methanol as eluent. Crystals suitable for X-ray analysis were obtained by the recrystallization of the ether from a mixture of hexane/ethyl acetate (1:2) (yield; 296 mg, 59%).