1-(4-Methyl­benz­yl)-1H-benzimidazol-2(3H)-one

Dounia Belaziz; Youssef Kandri Rodi; Fouad Ouazzani Chahdi; El Mokhtar Essassi; Mohamed Saadi; Lahcen El Ammari

doi:10.1107/S1600536812050726

. 2012 Dec 22;69(Pt 1):o122. doi: 10.1107/S1600536812050726

1-(4-Methylbenzyl)-1H-benzimidazol-2(3H)-one

Dounia Belaziz ^a,^*, Youssef Kandri Rodi ^a, Fouad Ouazzani Chahdi ^a, El Mokhtar Essassi ^b,^c, Mohamed Saadi ^d, Lahcen El Ammari ^d

PMCID: PMC3588251 PMID: 23476384

Abstract

In the title compound, C₁₅H₁₄N₂O, the fused five- and six-membered ring system is essentially planar, the maximum deviation from the mean plane being 0.009 (1) Å. The benzimidazol-2(3H)-one residue is nearly perpendicular to the benzyl ring, forming a dihedral angle of 77.41 (6)°. In the crystal, inversion dimers are formed by pairs of N—H⋯O hydrogen bonds; these dimers are linked by weak C—H⋯O interactions into a two-dimensional array in the (102) plane.

Related literature

For pharmacological and biochemical properties of benzimidazole derivatives, see: Lee et al. (2004 ▶); Deligeorgiev et al. (2011 ▶); Scott et al. (2002 ▶); Gothelf et al. (1998 ▶). For related structures, see: Belaziz et al. (2012 ▶); Ouzidan et al. (2011 ▶).

Experimental

Crystal data

C₁₅H₁₄N₂O
M _r = 238.28
Monoclinic,
a = 12.5585 (5) Å
b = 5.7181 (2) Å
c = 17.4153 (7) Å
β = 95.277 (2)°
V = 1245.31 (8) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 296 K
0.51 × 0.42 × 0.15 mm

Data collection

Bruker X8 APEXII diffractometer
16486 measured reflections
3211 independent reflections
2157 reflections with I > 2σ(I)
R _int = 0.029

Refinement

R[F ² > 2σ(F ²)] = 0.044
wR(F ²) = 0.122
S = 1.02
3211 reflections
164 parameters
H-atom parameters constrained
Δρ_max = 0.17 e Å⁻³
Δρ_min = −0.15 e Å⁻³

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); 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, 2012 ▶); software used to prepare material for publication: PLATON (Spek, 2009 ▶) and publCIF (Westrip,2010 ▶).

Supplementary Material

Click here for additional data file.^{(22.7KB, cif)}

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812050726/tk5182sup1.cif

e-69-0o122-sup1.cif^{(22.7KB, cif)}

Click here for additional data file.^{(157.6KB, hkl)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812050726/tk5182Isup2.hkl

e-69-0o122-Isup2.hkl^{(157.6KB, hkl)}

Click here for additional data file.^{(5KB, cml)}

Supplementary material file. DOI: 10.1107/S1600536812050726/tk5182Isup3.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—H1N1⋯O1ⁱ	0.94	1.91	2.8317 (15)	166
C15—H15C⋯O1ⁱⁱ	0.96	2.58	3.514 (2)	165
C8—H8A⋯O1ⁱⁱⁱ	0.97	2.61	3.5504 (18)	164

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

Acknowledgments

The authors thank the Unit of Support for Technical and Scientific Research (UATRS, CNRST) for the X-ray measurements.

supplementary crystallographic information

Comment

The development of benzimidazole derivatives has experienced in recent years, a considerable expansion following reports of biological activities presented by this type of compound. Benzimidazole derivatives are endowed with anti-viral, anti-ulcer, anti-hypertensive and anti-cancer activities (Lee et al., 2004; Deligeorgiev et al., 2011; Scott et al., 2002). Heterocycles containing the benzimidazole nucleus are also antagonists of a number of biological receptors, namely angiotensin II and prostaglandin D2 (Gothelf et al., 1998).

In a previous study, we reacted benzimidazol-2-one with dodecyl bromide in the presence of a catalytic quantity of tetra-n-butylammonium bromide under mild conditions to form 1-dodecyl-1H-benzimidazol-2(3H)-one (Belaziz et al., 2012; Ouzidan et al., 2011). The study is extended to the synthesis of new benzimidazol-2-one derivative by action of methylbenzyl bromide with 1H-benzimidazol-2(3H)-one to form the title compound (Scheme 1).

The crystal structure of the title compound, C₁₅H₁₄N₂O, is built up from two fused five- and six-membered rings (C1-C7,N1,N2,O1) linked to (C8-C15) the p-methyl-benzyl residue as shown in Fig. 1. The fused-ring system is essentially planar, with the maximum deviation of 0.009 (1) Å for the N2 atom. The dihedral angle between the benzimidazol-2(3H-one system and the (C9 to C14) benzyl ring is 77.41 (6)°.

In the crystal, inversion dimers are linked by N1—H1N···O1 hydrogen bonds. These are linked by weak C8–H8A···O1 and C15–H15C···O1 non-classic hydrogen bonds to form a layer parallel to (1 0 2); see Fig. 2 and Table 1.

Experimental

To 1H-benzimidazol-2(3H)-one (0.2 g, 1.49 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 methyl benzyl bromide (0.33 g, 1.78 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 hexane to give colorless crystals.