1-Benzyl-1H-benzimidazol-2(3H)-one

Younes Ouzidan; El Mokhtar Essassi; Santiago V Luis; Michael Bolte; Lahcen El Ammari

doi:10.1107/S160053681102455X

. 2011 Jun 25;67(Pt 7):o1822. doi: 10.1107/S160053681102455X

1-Benzyl-1H-benzimidazol-2(3H)-one

Younes Ouzidan ^a,^*, El Mokhtar Essassi ^b, Santiago V Luis ^c, Michael Bolte ^d, Lahcen El Ammari ^e

PMCID: PMC3151763 PMID: 21837191

Abstract

The fused five- and six-membered rings in the title compound, C₁₄H₁₂N₂O, are essentially planar, the largest deviation from the mean plane being 0.023 (2) Å. The dihedral angle between the benzimidazole mean plane and the phenyl ring is 68.50 (6)°. In the crystal, each molecule is linked to its symmetry equivalent created by a crystallographic inversion center by pairs of N—H⋯O hydrogen bonds, forming inversion dimers.

Related literature

For the biological activity of benzimidazole derivatives, see: Gravatt et al. (1994 ▶); Horton et al. (2003 ▶); Kim et al. (1996 ▶); Roth et al. (1997 ▶). For related structures, see: Ouzidan et al. (2011a ▶,b ▶).

Experimental

Crystal data

C₁₄H₁₂N₂O
M _r = 224.26
Monoclinic,
a = 13.8652 (7) Å
b = 5.7975 (3) Å
c = 14.9337 (7) Å
β = 109.5346 (12)°
V = 1131.33 (10) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 298 K
0.50 × 0.44 × 0.28 mm

Data collection

Bruker CCD three-circle diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.959, T _max = 0.977
9007 measured reflections
3392 independent reflections
2514 reflections with I > 2σ(I)
R _int = 0.020

Refinement

R[F ² > 2σ(F ²)] = 0.045
wR(F ²) = 0.126
S = 1.05
3392 reflections
166 parameters
H-atom parameters constrained
Δρ_max = 0.21 e Å⁻³
Δρ_min = −0.19 e Å⁻³

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

Supplementary Material

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S160053681102455X/im2298sup1.cif

e-67-o1822-sup1.cif^{(15.5KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681102455X/im2298Isup2.hkl

e-67-o1822-Isup2.hkl^{(166.4KB, hkl)}

Supplementary material file. DOI: 10.1107/S160053681102455X/im2298Isup3.cml

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
N1—H1⋯O1ⁱ	0.86	2.03	2.845 (1)	158

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Symmetry code: (i) Inline graphic .

supplementary crystallographic information

Comment

Benzimidazoles are very useful intermediates/subunits for the development of molecules of pharmaceutical or biological interest and its derivatives are an important class of bioactive molecules in the field of drugs and pharmaceuticals. Benzimidazole derivatives have found applications in diverse therapeutic areas including anti-ulcers, anti-hypertensives, anti-virals, anti-fungals, anti-cancers, (Gravatt et al. 1994; Horton et al. 2003; Kim et al. 1996; Roth et al. 1997).

As a continuation of our research work devoted to the development of substituted benzimidazol-2-one derivatives (Ouzidan et al., 2011a, 2011b), we report in this paper the synthesis of a new benzimidazol-2-one derivative by action of benzyl chloride with 1H-benzimidazol-2-one in the presence of a catalytic quantity of tetra-n-butylammonium bromide under mild conditions to furnish the title compound (Scheme 1).

The two fused five and six-membered rings are almost planar with the maximum deviation of 0.023 (2) Å from C2. The dihedral angle between the benzimidazole system and the phenyl ring is 68.50 (6)° (Fig.1). In the crystal structure each molecule is linked to its symmetry equivalent created by the crystallographic inversion center by N–H···O hydrogen bonds to form pseudo-dimers as shown in Fg.2.

Experimental

To 1H-benzimidazol-2-one (0.2 g, 1.5 mmol), potassium carbonate (0.41 g, 3 mmol) and tetra-n-butylammonium bromide (0.05 g, 0.15 mmol) in DMF (15 ml) was added benzyl chloride (0.34 ml, 3 mmol). Stirring was continued at room temperature for 6 h. The salt was removed by filtration and the filtrate concentrated under reduced pressure. The residue was separated by chromatography on a column of silica gel with ethyl acetate/hexane (1/2) as eluent. The compound was recrystallized from ethanol to give colorless crystals (yield: 12%).