1-Decyl-6-nitro-1H-benzimidazol-2(3H)-one

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

doi:10.1107/S1600536811041389

. 2011 Oct 12;67(Pt 11):o2937. doi: 10.1107/S1600536811041389

1-Decyl-6-nitro-1H-benzimidazol-2(3H)-one

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

PMCID: PMC3247349 PMID: 22219967

Abstract

The title molecule, C₁₇H₂₅N₃O₃, is built up from fused six- and five-membered rings linked to a –C₁₀H₂₁ chain. The fused-ring system is essentially planar, the largest deviation from the mean plane being 0.009 (2) Å. The chain is roughly perpendicular to this plane, making a dihedral angle of 79.5 (2)°. In the crystal, N—H⋯O hydrogen bonds build infinite chains along [010]. There are channels in the structure containing disordered hexane. The contribution of this solvent to the scattering power was suppressed using the SQUEEZE option in PLATON [Spek (2009 ▶). Acta Cryst. D65, 148–155].

Related literature

For the pharmacological and biochemical properties of related compounds, 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

C₁₇H₂₅N₃O₃
M _r = 319.40
Monoclinic,
a = 32.9827 (6) Å
b = 4.55881 (9) Å
c = 29.3435 (5) Å
β = 109.481 (2)°
V = 4159.56 (13) Å³
Z = 8
Cu Kα radiation
μ = 0.57 mm⁻¹
T = 206 K
0.15 × 0.11 × 0.05 mm

Data collection

Agilent SuperNova Dual (Cu at zero) Atlas diffractometer
Absorption correction: analytical [CrysAlis PRO (Agilent, 2011) ▶ based on expressions derived by Clark & Reid (1995 ▶)] T _min = 0.952, T _max = 0.985
20838 measured reflections
4129 independent reflections
3475 reflections with I > 2σ(I)
R _int = 0.029

Refinement

R[F ² > 2σ(F ²)] = 0.041
wR(F ²) = 0.126
S = 1.09
4129 reflections
208 parameters
H-atom parameters constrained
Δρ_max = 0.16 e Å⁻³
Δρ_min = −0.17 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/S1600536811041389/im2324sup1.cif

e-67-o2937-sup1.cif^{(25.9KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811041389/im2324Isup2.hkl

e-67-o2937-Isup2.hkl^{(198.4KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811041389/im2324Isup3.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	1.88	2.743 (1)	178

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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. Benzimidazole derivatives have found applications in diverse therapeutic areas including anti-ulcers, anti-hypertensives, anti-virals, anti-fungals and 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 1-bromodecane with 5-nitro-1,3-dihydro-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 molecular structure of 1-decyl-6-nitro-1,3-dihydro-benzimidazol-2-one is built up from two fused six-and five-membered rings linked to a C₁₀H₂₁ chain as schown in Fg.1. The fused rings are essentially planar, with maximum deviations of 0.008 (2) Å and -0.004 (2) Å for C2 and N1, respectively. The dihedral angle between them does not exceed 0.68 (7)°. The torsional angles C7–N2–C11–C12 and C17–C18–C19–C20 are -98.4 (2) ° and 176.7 (2)°, respectively. N1—H···O1 hydrogen bonds build up infinite one-dimensional chains along the [0 1 0] direction as shown in Fig.2 and Table 1.

Experimental

To 5-nitro-1,3-dihydro-benzimidazol-2-one (0.2 g, 1.1 mmol), potassium carbonate (0.30 g, 2.2 mmol) and tetra-n-butylammonium bromide (0.07 g, 0.2 mmol) in DMF (15 ml) was added 1-bromodecane (0.34 ml, 1.65 mmol). Stirring was continued at room temperature for 6 h. The precipitated salt was removed by filtration and the filtrate was concentrated under reduced pressure. The residue was separated by chromatography on a column of silica gel with ethyl acetate/hexane (1/2) as eluent. Colorless crystals were isolated when the solvent was allowed to evaporate (yield: 27%).