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

Younes Ouzidan; Youssef Kandri Rodi; El Mokhtar Essassi; Lahcen El Ammari; Frank R Fronczek; Ramaiyer Venkatraman

doi:10.1107/S1600536811005654

. 2011 Feb 19;67(Pt 3):o669. doi: 10.1107/S1600536811005654

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

Younes Ouzidan ^a, Youssef Kandri Rodi ^a,^*, El Mokhtar Essassi ^b, Lahcen El Ammari ^c, Frank R Fronczek ^d, Ramaiyer Venkatraman ^e

PMCID: PMC3052022 PMID: 21522418

Abstract

In the title molecule, C₁₆H₂₃N₃O₃, the dihedral angle between the benzimidazole and nitro group planes is 5.34 (9)° and the dihedral angle between the benzimidazole and aliphatic chain mean planes is 73.23 (5)°. The C—C—C—C torsion angles (about Inline graphic 176°) of the nonyl group indicate an all-antiperiplanar conformation. In the crystal, adjacent molecules are linked by pairs of N—H⋯O hydrogen bonds into inversion dimers. These molecules are further connected through C—H⋯O interactions, building tapes parallel to (22).

Related literature

For background to the pharmacological and biochemical properties of benzimidazolones, see: Gbadamassi et al. (1988 ▶); Singh et al. (2000 ▶); Derand et al. (2003 ▶); Badarau et al. (2009 ▶). For similar structures, see: Saber et al. (2010 ▶); Ouzidan et al. (2011 ▶).

Experimental

Crystal data

C₁₆H₂₃N₃O₃
M _r = 305.37
Triclinic,
a = 5.483 (1) Å
b = 10.2092 (15) Å
c = 14.746 (3) Å
α = 74.275 (9)°
β = 79.727 (6)°
γ = 83.410 (8)°
V = 779.9 (2) Å³
Z = 2
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 90 K
0.35 × 0.27 × 0.22 mm

Data collection

Nonius KappaCCD diffractometer
21087 measured reflections
6349 independent reflections
5183 reflections with I > 2σ(I)
R _int = 0.023

Refinement

R[F ² > 2σ(F ²)] = 0.040
wR(F ²) = 0.113
S = 1.03
6349 reflections
201 parameters
H-atom parameters constrained
Δρ_max = 0.45 e Å⁻³
Δρ_min = −0.28 e Å⁻³

Data collection: COLLECT (Nonius, 2000 ▶); cell refinement: SCALEPACK (Otwinowski & Minor, 1997 ▶); data reduction: DENZO (Otwinowski & Minor, 1997 ▶) and SCALEPACK; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811005654/gk2342sup1.cif

e-67-0o669-sup1.cif^{(26.6KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811005654/gk2342Isup2.hkl

e-67-0o669-Isup2.hkl^{(304.4KB, hkl)}

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	0.88	1.89	2.7651 (9)	170
C6—H6⋯O3ⁱⁱ	0.95	2.58	3.3139 (11)	134

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

supplementary crystallographic information

Comment

Benzimidazoles are useful intermediates/subunits for the development of molecules of pharmaceutical or biological interest (Gbadamassi et al., 1988). Benzimidazolone and its derivatives are also an important class of bioactive molecules in the field of drugs and pharmaceuticals (Derand et al., 2003). They found potential applications in diverse therapeutic areas including, anti-hypertensives and anti-virals (Badarau et al., 2009; Singh et al., 2000). The structural studies of benzimidazolone, linked to an isopropenyl and nonyl group respectively, have been published by Saber et al. (2010)and Ouzidan et al. (2011).

The 5-nitro-1-nonyl-1H-benzimidazol-2(3H)-one molecule structure is built up from two fused six-and five-membered rings linked to C₉H₁₉ chain as shown in Fig.1. The aliphatic chain has all-antiperiplanar (all-trans) conformation. Furthermore, the fused-ring system and the nitro group are almost planar, with a maximum deviation of 0.0414 (8) Å and 0.0250 (7) Å for C4 and N1 respectively. The dihedral angle between the two rings and nitro group planes is 5.34 (9)°. The torsion angles C1 N2 C8 C9 and C13 C14 C15 C16 are 113.66 (8)° and 177.26 (7)° respectively.

In the crystal, adjacent molecules are linked by pairs of N—H···O hydrogen bonds into inversion dimers. These molecules are further connected through C—H···O hydrogen bonds into a tape parallel to the (-1 2 2) plane, as schown in Fig. 2 and Table 1.

Experimental

To 5-nitro-1H-benzoimidazol-2(3H)-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-bromononane (0.43 ml, 2.2 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. Colorless needle-shaped crystals were isolated when the solvent was allowed to evaporate [(m.p. 392–394 K (ethanol)].