1-Dodecyl-1H-benzo[d]imidazol-2(3H)-one

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

doi:10.1107/S1600536812041189

. 2012 Oct 6;68(Pt 11):o3069. doi: 10.1107/S1600536812041189

1-Dodecyl-1H-benzo[d]imidazol-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: PMC3515176 PMID: 23284403

Abstract

In the title compound, C₁₉H₃₀N₂O, the fused ring system is essentially planar, the maximum deviation from the mean plane being 0.013 (2) Å for the N atom bearing the dodecyl chain. The 1-dodecyl group is almost perpendicular to the 1H-benzo[d]imidazol-2(3H)-one plane as indicated by the dihedral angle of 82.9 (2)°between planes through the fused ring system and the first three C atoms of the chain. The C—C—C—C torsion angles (about ±179°) of the dodecyl group indicate an antiperiplanar conformation. In the crystal, inversion dimers are formed by pairs of N—H⋯O hydrogen bonds.

Related literature

For pharmacological and biochemical properties of benzimidazoles and their derivatives, see: Al Muhaimeed (1997 ▶); Scott et al. (2002 ▶); Nakano et al. (2000 ▶); Zhu et al. (2000 ▶); Zarrinmayeh et al. (1998 ▶). For compounds with closely related structures, see: Ouzidan et al. (2011 ▶); Kandri Rodi et al. (2011 ▶); Belaziz et al. (2012 ▶).

Experimental

Crystal data

C₁₉H₃₀N₂O
M _r = 302.45
Monoclinic,
a = 38.3223 (14) Å
b = 4.8318 (2) Å
c = 21.9831 (8) Å
β = 117.843 (2)°
V = 3599.3 (2) Å³
Z = 8
Mo Kα radiation
μ = 0.07 mm⁻¹
T = 296 K
0.47 × 0.31 × 0.14 mm

Data collection

Bruker X8 APEX Diffractometer
29002 measured reflections
4637 independent reflections
3179 reflections with I > 2σ(I)
R _int = 0.028

Refinement

R[F ² > 2σ(F ²)] = 0.045
wR(F ²) = 0.141
S = 1.01
4637 reflections
199 parameters
H-atom parameters constrained
Δρ_max = 0.21 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); 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: PLATON (Spek, 2009 ▶) and publCIF (Westrip, 2010 ▶).

Supplementary Material

Click here for additional data file.^{(27.3KB, cif)}

Crystal structure: contains datablock(s) I. DOI: 10.1107/S1600536812041189/im2402sup1.cif

e-68-o3069-sup1.cif^{(27.3KB, cif)}

Click here for additional data file.^{(222.7KB, hkl)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812041189/im2402Isup2.hkl

e-68-o3069-Isup2.hkl^{(222.7KB, hkl)}

Click here for additional data file.^{(7KB, cml)}

Supplementary material file. DOI: 10.1107/S1600536812041189/im2402Isup3.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	1.97	2.815 (1)	168

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Symmetry code: (i) Inline graphic .

Acknowledgments

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

supplementary crystallographic information

Comment

Benzimidazoles and their derivatives exhibit a number of important pharmacological properties, such as antihistaminic (Al Muhaimeed, 1997) anti-ulcerative (Scott et al., 2002) and antiallergic (Nakano et al., 2000). In addition, benzimidazole derivatives are effective against the human cytomegalovirus (HCMV) (Zhu et al., 2000) and are also efficient selective neuropeptide Y Y1 receptor antagonists (Zarrinmayeh et al., 1998).

In a previous study, we reacted benzimidazol-2-one with octyl bromide in the presence of a catalytic quantity of tetra-n-butylammonium bromide under mild conditions to form 1-octyl-1H-benzo[d]imidazol-2(3H)-one (Belaziz et al., 2012). The study has been extended to the synthesis of a new benzimidazol-2-one derivative by action of dodecyl bromide with 1H-benzo[d]imidazol-2(3H)-one to form the title compound (Scheme 1).

The molecular structure of 1-dodecyl-1H-benzo[d]imidazol-2(3H)-one is built up from fused six-and five-membered rings linked to a C₁₂H₂₅ chain as shown in Fig. 1. The fused-ring system is essentially planar, with a maximum deviation of -0.013 (2) Å for N2. The dodecyl group is almost perpendicular to the 1H-benzo[d]imidazol-2(3H)-one plane as indicated by the dihedral angle between planes (C8 C9 C10) and (N1 N2 C1 to C7) of 82.9 (2)° and by the torsion angle (C7 N2 C8 C9) = -84.3 (2)°. In the crystal structure, inversion dimers are formed by N—H···O hydrogen bonds. in the way to form dimers (Fig. 2).

The structure of the title compound is almost identical to that observed for the following molecules: 1-nonyl-1H-benzimidazol-2(3H)-one, 1-octyl-1H-benzimidazol-2(3H)-one and 5-chloro-1-nonyl-1H-benzimidazol-2(3H)-one (Ouzidan et al., 2011, Kandri Rodi et al. 2011). Nevertheless, the different lengths of the chains leads to different unit cells with different crystal symmetry.

Experimental

To 1H-benzo[d]imidazol-2(3H)-one (0.2 g, 1.49 mmol), potassium carbonate (0.41 g, 2.98 mmol) and tetra-n-butylammonium bromide (0.05 g, 0.15 mmol) in DMF (15 ml) was added dodecyl bromide (0.30 ml, 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 (yield: 65%). The compound was recrystallized from hexan/acetate to give colourless crystals.