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

Mohandas, T.; Jayamoorthy, K.; Jayabharathi, J.; Sakthivel, P.

doi:10.1107/S1600536813001566

Volume 69
Part 2
Pages o269-o270
February 2013

Received 20 November 2012
Accepted 16 January 2013
Online 23 January 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.002 Å
R = 0.035
wR = 0.092
Data-to-parameter ratio = 13.1
Details

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

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

^aShri Angalamman College of Engineering and Technology, Siruganoor, Tiruchirappalli 621 105, India,^bDepartment of Chemistry, Annamalai University, Annamalainagar 608 002, Tamilnadu, India, and ^cDepartment of Physics, Urumu Dhanalakshmi College, Tiruchirappalli 620 019, India
Correspondence e-mail: sakthi2udc@gmail.com

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 [pi] 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, P 2₁ /c
a = 12.3220 (3) Å
b = 7.3030 (2) Å
c = 18.2450 (3) Å
= 108.909 (1)°
V = 1553.22 (6) Å³
Z = 4
Mo K radiation
= 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 > 2(I)
R_int = 0.024

Refinement

R[F² > 2(F²)] = 0.035
wR(F²) = 0.092
S = 1.03
2728 reflections
209 parameters
H-atom parameters constrained
_max = 0.11 e Å^-3
_min = -0.21 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

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

D-HA	D-H	HA	DA	D-HA
C6-H6Cg2ⁱ	0.93	2.86	3.5361 (15)	130
C13-H13Cg3ⁱⁱ	0.93	2.83	3.4594 (16)	126
Symmetry codes: (i) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[-x+2, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

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 data and figures for this paper are available from the IUCr electronic archives (Reference: GO2077 ).

References

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organic compounds