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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 [sigma](C-C) = 0.002 Å
R = 0.035
wR = 0.092
Data-to-parameter ratio = 13.1
Details
Open access

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

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[Mason, J. S., Morize, I., Menard, P. R., Cheney, D. L., Hume, C. & Labaudiniere, R. F. (1999). J. Med. Chem. 42, 3251-3264.]). For their biological activities such as antimicrobial & anticancer, antidiabetic, antifungal, anti HIV and antiviral, see: Demirayak et al. (2002[Demirayak, S., Abu Mohsen, U. & Lagri Karaburun, A. (2002). Eur. J. Med. Chem. 37, 255-260.]); Minoura et al. (2004[Minoura, H., Takeshita, S., Ita, M., Hirosumi, J., Mabuchi, M., Kawamura, I., Nakajima, S., Nakayama, O., Kayakiri, H., Oku, T., Ohkubo-Suzuki, A., Fukagawa, M., Kojo, H., Hanioka, K., Yamasaki, N., Imoto, T., Kobayashi, Y. & Mutoh, S. (2004). Eur. J. Pharmacol. 494, 273-281.]); Pawar et al. (2004[Pawar, N. S., Dalal, D. S., Shimpi, S. R. & Mahulikar, P. P. (2004). Eur. J. Pharm. Sci. 21, 115-118.]); Rao et al. (2003[Rao, A., Chimirri, A., De Clercq, E., Maria Monforte, A., Monforte, P., Pannecouque, C. & Zappala, M. (2003). Il Farmaco, 58, 259-263.]); Tomei et al. (2003[Tomei, L., Altamura, S., Bartholomew, L., Biroccio, A., Ceccacci, A., Pacini, L., Narjes, F., Gennari, N., Bisbocci, M., Incitti, I., Orsatti, L., Harper, S., Stansfield, I., Rowley, M., De Francesco, R. & Migliaccio, G. (2003). J. Virol. 77, 13225-13231.]). For their action as polymerase and transcriptase inhibitors, see: Beaulieu et al. (2004[Beaulieu, P. L., Bos, M., Bousquet, Y., Fazal, G., Gauthier, J., Gillard, J., Goulet, S., LaPlante, S., Poupart, M. A., Lefebvre, S., McKerche, G., Pellerin, C., Austel, V. & Kukolj, G. (2004). Bioorg. Med. Chem. Lett. 14, 119-124.]; Morningstar et al. (2007[Morningstar, M. L., Roth, T., Farnsworth, D. W., Smith, M. K., Watson, K., Buckheit, R. W., Das, K., Zhang, W., Arnold, E. & Julias, J. G. (2007). J. Med. Chem. 50, 4003-4015.]); Roth et al. (1997[Roth, T., Morningstar, M. L., Boyer, P. L., Hughes, S. H., Buckheit, J. R. W. & Michejda, C. J. (1997). J. Med. Chem. 40, 4199-4207.]); For other related studies, see: Jayabharathi et al. (2012[Jayabharathi, J., Thanikachalam, V., Rajendraprasath, N., Saravanan, K. & Venkatesh Perumal, M. (2012). Med. Chem. Res. 21, 1850-1860.])

[Scheme 1]

Experimental

Crystal data
  • C20H16N2O

  • Mr = 300.35

  • Monoclinic, P 21 /c

  • a = 12.3220 (3) Å

  • b = 7.3030 (2) Å

  • c = 18.2450 (3) Å

  • [beta] = 108.909 (1)°

  • V = 1553.22 (6) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 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[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.956, Tmax = 0.999

  • 13787 measured reflections

  • 2728 independent reflections

  • 2283 reflections with I > 2[sigma](I)

  • Rint = 0.024

Refinement
  • R[F2 > 2[sigma](F2)] = 0.035

  • wR(F2) = 0.092

  • S = 1.03

  • 2728 reflections

  • 209 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.11 e Å-3

  • [Delta][rho]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-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
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[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: APEX2 and SAINT (Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); software used to prepare material for publication: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).


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


References

Beaulieu, P. L., Bos, M., Bousquet, Y., Fazal, G., Gauthier, J., Gillard, J., Goulet, S., LaPlante, S., Poupart, M. A., Lefebvre, S., McKerche, G., Pellerin, C., Austel, V. & Kukolj, G. (2004). Bioorg. Med. Chem. Lett. 14, 119-124.  [CrossRef] [PubMed] [ChemPort]
Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Demirayak, S., Abu Mohsen, U. & Lagri Karaburun, A. (2002). Eur. J. Med. Chem. 37, 255-260.  [ISI] [CrossRef] [PubMed] [ChemPort]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Jayabharathi, J., Thanikachalam, V., Rajendraprasath, N., Saravanan, K. & Venkatesh Perumal, M. (2012). Med. Chem. Res. 21, 1850-1860.  [ISI] [CSD] [CrossRef] [ChemPort]
Mason, J. S., Morize, I., Menard, P. R., Cheney, D. L., Hume, C. & Labaudiniere, R. F. (1999). J. Med. Chem. 42, 3251-3264.  [ISI] [CrossRef] [PubMed] [ChemPort]
Minoura, H., Takeshita, S., Ita, M., Hirosumi, J., Mabuchi, M., Kawamura, I., Nakajima, S., Nakayama, O., Kayakiri, H., Oku, T., Ohkubo-Suzuki, A., Fukagawa, M., Kojo, H., Hanioka, K., Yamasaki, N., Imoto, T., Kobayashi, Y. & Mutoh, S. (2004). Eur. J. Pharmacol. 494, 273-281.  [ISI] [CrossRef] [PubMed] [ChemPort]
Morningstar, M. L., Roth, T., Farnsworth, D. W., Smith, M. K., Watson, K., Buckheit, R. W., Das, K., Zhang, W., Arnold, E. & Julias, J. G. (2007). J. Med. Chem. 50, 4003-4015.  [ISI] [CrossRef] [PubMed] [ChemPort]
Pawar, N. S., Dalal, D. S., Shimpi, S. R. & Mahulikar, P. P. (2004). Eur. J. Pharm. Sci. 21, 115-118.  [ISI] [CrossRef] [PubMed] [ChemPort]
Rao, A., Chimirri, A., De Clercq, E., Maria Monforte, A., Monforte, P., Pannecouque, C. & Zappala, M. (2003). Il Farmaco, 58, 259-263.  [CrossRef] [PubMed]
Roth, T., Morningstar, M. L., Boyer, P. L., Hughes, S. H., Buckheit, J. R. W. & Michejda, C. J. (1997). J. Med. Chem. 40, 4199-4207.  [ISI] [CrossRef] [ChemPort] [PubMed]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]
Tomei, L., Altamura, S., Bartholomew, L., Biroccio, A., Ceccacci, A., Pacini, L., Narjes, F., Gennari, N., Bisbocci, M., Incitti, I., Orsatti, L., Harper, S., Stansfield, I., Rowley, M., De Francesco, R. & Migliaccio, G. (2003). J. Virol. 77, 13225-13231.  [CrossRef] [PubMed] [ChemPort]


Acta Cryst (2013). E69, o269-o270   [ doi:10.1107/S1600536813001566 ]

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