2-(4-Meth­oxy­phen­yl)-1-phenyl-1H-benzimidazole

T Mohandas; K Jayamoorthy; J Jayabharathi; P Sakthivel

doi:10.1107/S1600536813001566

. 2013 Jan 23;69(Pt 2):o269–o270. doi: 10.1107/S1600536813001566

2-(4-Methoxyphenyl)-1-phenyl-1H-benzimidazole

T Mohandas ^a, K Jayamoorthy ^b, J Jayabharathi ^b, P Sakthivel ^c,^*

PMCID: PMC3569798 PMID: 23424544

Abstract

In the title compound, C₂₀H₁₆N₂O, the 1H-benzimidazole ring forms dihedral angles of 48.00 (6) and 64.48 (6)°, respectively with the benzene and phenyl rings, which are inclined to one another by 58.51 (7)°. In the crystal, weak C—H⋯π interactions are the only intermolecular interactions present.

Related literature

For background to benzimidazole derivatives, see: Mason et al. (1999 ▶). For their biological activities such as antimicrobial & anticancer, antidiabetic, antifungal, anti HIV and antiviral, see: Demirayak et al. (2002 ▶); Minoura et al. (2004 ▶); Pawar et al. (2004 ▶); Rao et al. (2003 ▶); Tomei et al. (2003 ▶). For their action as polymerase and transcriptase inhibitors, see: Beaulieu et al. (2004 ▶; Morningstar et al. (2007 ▶); Roth et al. (1997 ▶); For other related studies, see: Jayabharathi et al. (2012 ▶)

Experimental

Crystal data

C₂₀H₁₆N₂O
M _r = 300.35
Monoclinic,
a = 12.3220 (3) Å
b = 7.3030 (2) Å
c = 18.2450 (3) Å
β = 108.909 (1)°
V = 1553.22 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 293 K
0.30 × 0.30 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T _min = 0.956, T _max = 0.999
13787 measured reflections
2728 independent reflections
2283 reflections with I > 2σ(I)
R _int = 0.024

Refinement

R[F ² > 2σ(F ²)] = 0.035
wR(F ²) = 0.092
S = 1.03
2728 reflections
209 parameters
H-atom parameters constrained
Δρ_max = 0.11 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: APEX2 and SAINT (Bruker, 2008 ▶); 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 (Farrugia, 2012 ▶); software used to prepare material for publication: PLATON (Spek, 2009 ▶).

Supplementary Material

Click here for additional data file.^{(26KB, cif)}

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813001566/go2077sup1.cif

e-69-0o269-sup1.cif^{(26KB, cif)}

Click here for additional data file.^{(131.2KB, hkl)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813001566/go2077Isup2.hkl

e-69-0o269-Isup2.hkl^{(131.2KB, hkl)}

Click here for additional data file.^{(6.1KB, cml)}

Supplementary material file. DOI: 10.1107/S1600536813001566/go2077Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

Cg2 and Cg3 are the centroids of the C2–C7 and C9–C14 phenyl rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6⋯Cg2ⁱ	0.93	2.86	3.5361 (15)	130
C13—H13⋯Cg3ⁱⁱ	0.93	2.83	3.4594 (16)	126

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

supplementary crystallographic information

Comment

The benzimidazole core is classified by medicinal chemists as one of the 'privileged substructures' for drug design,in light of the affinity they display towards a variety of enzymes and protein receptors (Mason et al.,1999).

The synthesis of benzimidazoles has received much attention owing to the varied biological activity such as antifungal (Pawar et al., 2004), antiviral (Tomei et al., 2003), antiHIV (Rao et al., 2003), antidiabetic (Minoura et al., 2004), antimicrobial and anticancer (Demirayak et al., 2002), properties exhibited by a number of derivatives of these compounds.

Benzimidazole derivatives possess antioxidant activities (Jayabharathi et al.,2012).

They have emerged as potent non nucleoside inhibitors of HIV-1 reverse transcriptase (Roth et al.,1997, Morningstar et al.,2007)

It also acts as a specific inhibitors of the NS5B polymerase of the hepatitis C virus (HCV) (Beaulieu, et al., 2004).

The molecular structure of (I), is shown in Fig.1. The (N1/N2/C8—C14) 1H-benzimidazole ring is planar. It forms dihedral angles of 48.00 (6)° and 64.48 (6)° with the mean planes of the C2—C7 and C15—C20 phenyl rings respectively.

The C1—O1—C2—C7 and C3—C2—O1—C1 torsion angles are 2.8 (2)° and -176.42 (14)° respectively.

A C6—H6···π interaction involving the phenyl ring of methoxybenzene at the symmetry code [1 - x,1/2 + y,1/2 - z] and C13—H13···π interaction involving the benzene ring of benzimidazole at the symmetry code [2 - x,1/2 + y,1/2 - z] are also found.

Experimental

To pure N-phenyl-0-phenylenediamine(17 mmol,3.128 g) in ethanol(10 ml), 4-methoxy benzaldehyde(17 mmol,2.1 ml) and ammonium acetate(3 g) was added for about 1 h while maintaining the temperature at 80°C. The reaction mixture was refluxed and the completion of reaction was monitored by TLC, finally the reactants extracted with dichloromethane. The solid separated was purified by column chromatography using petroleum ether as the eluent.Yield:2.65 g(50%) from which it was crystallized.