5-Chloro-1-nonyl-1H-benzimidazol-2(3H)-one

Youssef Kandri Rodi; Fouad Ouazzani Chahdi; El Mokhtar Essassi; Santiago V Luis; Michael Bolte; Lahcen El Ammari

doi:10.1107/S1600536811047829

. 2011 Nov 16;67(Pt 12):o3340–o3341. doi: 10.1107/S1600536811047829

5-Chloro-1-nonyl-1H-benzimidazol-2(3H)-one

Youssef Kandri Rodi ^a, Fouad Ouazzani Chahdi ^a,^*, El Mokhtar Essassi ^b, Santiago V Luis ^c, Michael Bolte ^d, Lahcen El Ammari ^e

PMCID: PMC3238987 PMID: 22199836

Abstract

The asymmetric unit of the title compound, C₁₆H₂₃ClN₂O, comtains two independent molecules in which the fused-ring systems are essentially planar, the largest deviation from the mean plane of each molecule being 0.011 (2) Å and 0.016 (2) Å. The benzimidazole rings of the two molecules make a dihedral angle of 66.65 (7)°. The nonyl substituents are almost perpendicular to the benzimidazole planes [C—N—C—C tosrsion angles = 96.0 (3) and 81.0 (2)°]. In the crystal, each independent molecule forms an inversion dimer via a pair of N—H⋯O hydrogen bonds. In one of the independent molecules, the terminal –CH₂–CH₃ group of the alkyl chain is disordered over two sets of sites with a refined occupancy ratio of 0.746 (7):0.254 (7).

Related literature

For the pharmacological, biochemical and structural properties of benzimidazolones, see: Al Muhaimeed (1997 ▶); Nakano et al. (2000 ▶); Scott et al. (2002 ▶); Zarrinmayeh et al. (1998 ▶); Zhu et al. (2000 ▶); Ouzidan et al. (2011a ▶,b ▶).

Experimental

Crystal data

C₁₆H₂₃ClN₂O
M _r = 294.81
Triclinic,
a = 5.51441 (17) Å
b = 15.6507 (4) Å
c = 20.0540 (6) Å
α = 71.807 (3)°
β = 86.612 (2)°
γ = 80.709 (2)°
V = 1622.59 (8) Å³
Z = 4
Cu Kα radiation
μ = 2.06 mm⁻¹
T = 296 K
0.43 × 0.20 × 0.16 mm

Data collection

Agilent SuperNova Dual (Cu at zero) Atlas diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.640, T _max = 0.720
31859 measured reflections
6416 independent reflections
5705 reflections with I > 2σ(I)
R _int = 0.031

Refinement

R[F ² > 2σ(F ²)] = 0.044
wR(F ²) = 0.124
S = 1.03
6416 reflections
379 parameters
9 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.46 e Å⁻³
Δρ_min = −0.32 e Å⁻³

Data collection: CrysAlis PRO (Agilent, 2011 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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: SHELXL97.

Supplementary Material

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811047829/im2336sup1.cif

e-67-o3340-sup1.cif^{(41.1KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811047829/im2336Isup2.hkl

e-67-o3340-Isup2.hkl^{(307.7KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811047829/im2336Isup3.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
N2—H2⋯O1ⁱ	0.83 (2)	1.96 (2)	2.778 (2)	170 (2)
N2A—H2A⋯O1Aⁱⁱ	0.85 (2)	1.95 (2)	2.7937 (18)	171.1 (19)

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

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).

As a continuation of our research work devoted to the development of substituted benzimidazol-2-one derivatives (Ouzidan et al., 2011a, 2011b), we report the synthesis of a new benzimidazol-2-one derivative by action of nonyl bromide with 5-chloro-1,3-dihydrobenzimidazol-2-one. The reaction provided the title compound (Scheme 1).

The asymmetric unit of the title compound, C₁₆H₂₃ClN₂O is built up from two independent molecules with different orientations as shown in Fig.1. The two fused five and six-membered rings building each molecule are almost planar with the maximum deviation of 0.011 (2) Å and 0.016 (2) Å for N2 in the first molecule (C1 to C19) and for C1A in the second molecule (C1A to C19A), respectively. The dihedral angle between the two benzimidazole rings is 66.65 (7)°. The nonyl groups are almost perpendicular to the benzimidazole planes as indicated by the torsion angles of C1—N1—C11—C12 = 96.0 (3) ° and C1A—N1A—C11A—C12A = 81.0 (2) °.

In the crystal structure, each molecule forms a hydrogen bonded centrosymmetrical dimer as shown in Fig.2.

Experimental

To 5-chloro-1,3-dihydrobenzimidazol-2-one (0.2 g, 1.18 mmol), potassium carbonate (0.33 g, 2.38 mmol), and tetra-n-butylammonium bromide (0.04 g, 0.11 mmol) in DMF (15 ml) was added nonyl bromide (0.34 ml, 1.78 mmol). Stirring was continued at room temperature for 6 h. The salts were 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: 34%). Single crystals were isolated when the solvent was allowed to evaporate at room temperature.