2-(1,3-Benzodioxol-5-yl)-1H-benzimid­azole

Nadir Ghichi; Mohamed Amine Benaouida; Ali Benosmane; Ali Benboudiaf; Hocine Merazig

doi:10.1107/S1600536814000737

. 2014 Jan 18;70(Pt 2):o157. doi: 10.1107/S1600536814000737

2-(1,3-Benzodioxol-5-yl)-1H-benzimidazole

Nadir Ghichi ^a, Mohamed Amine Benaouida ^a, Ali Benosmane ^a,^*, Ali Benboudiaf ^a, Hocine Merazig ^a

PMCID: PMC3998317 PMID: 24764878

Abstract

The asymmetric unit of the title compound, C₁₄H₁₀N₂O₂, contains two independent molecules. In each molecule, the benzodioxole ring system displays an envelope conformation, with the methylene C atom located at the flap deviating by 0.081 (2) and 0.230 (2) Å from the mean plane formed by the other atoms. The dihedral angles between the benzoimidazole ring system (all atoms) and the benzodioxole benzene ring are 15.35 (6) and 10.99 (7)°. In the crystal, molecules are linked by N—H⋯N hydrogen bonds into chains running along the [101].

Related literature

For the biological activity of imidazole derivatives and their use as inhibitors of neurodegenerative disorders and as antitumor drugs, see: Park et al. (1977 ▶). For related imidazole compounds, see: Andreani et al. (2005 ▶); Xu et al. (2010 ▶). graphic file with name e-70-0o157-scheme1.jpg

Experimental

Crystal data

C₁₄H₁₀N₂O₂
M _r = 238.24
Monoclinic,
a = 8.7454 (7) Å
b = 15.2824 (11) Å
c = 16.9487 (13) Å
β = 91.974 (5)°
V = 2263.9 (3) Å³
Z = 8
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 293 K
0.03 × 0.02 × 0.01 mm

Data collection

Nonius KappaCCD diffractometer
13101 measured reflections
4003 independent reflections
3422 reflections with I > 2σ(I)
R _int = 0.018

Refinement

R[F ² > 2σ(F ²)] = 0.034
wR(F ²) = 0.088
S = 1.02
4003 reflections
325 parameters
H-atom parameters constrained
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.18 e Å⁻³

Data collection: KappaCCD Server Software (Nonius, 1999 ▶); cell refinement: KappaCCD Server Software; data reduction: DENZO and SCALEPACK (Otwinowski & Minor, 1997 ▶); 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: SHELXL97.

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536814000737/xu5756sup1.cif

e-70-0o157-sup1.cif^{(21.2KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814000737/xu5756Isup2.hkl

e-70-0o157-Isup2.hkl^{(192.2KB, hkl)}

Click here for additional data file.^{(4.8KB, cml)}

Supporting information file. DOI: 10.1107/S1600536814000737/xu5756Isup3.cml

CCDC reference: http://scripts.iucr.org/cgi-bin/cr.cgi?rm=csd&csdid=981105

Additional supporting information: 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—H1N⋯N4ⁱ	0.86	1.93	2.7761 (15)	168
N3—H3N⋯N2	0.86	1.96	2.8053 (16)	168

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Symmetry code: (i) Inline graphic .

Acknowledgments

We thank all researchers of the CHEMS Research Unit, University of Constantine 1, Algeria, for their valuable assistance and the MESRS (Algeria) for financial support.

supplementary crystallographic information

1. Comment

Owing to the promising biological activities as inhibitors of neurodegenerative disorders and antitumor drugs (Park et al., 1977), most of these investigations were carried out with imidazole (Andreani et al., 2005; Xu et al., 2010).

A view of the molecular structure of (I) with numbering Scheme is Shown in Fig1. In the crystal, intermolecular N—H···N hydrogen bond Fig2, link the molecules into chains running along the [101] direction.

2. Experimental

A mixture of 1,2-diaminebenzene (2.3 g) and benzo[d][1,3]dioxole-5-carbaldehyde (0.02 mole) in ethanol (60 ml) was refluxed for 6 h. The yellow crystals obtained are filter and rinsed by a mixture of water ice ethanol, the recrystalization is done in excess of chloroform in 15 days.