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Volume 69 
Part 3 
Page o334  
March 2013  

Received 27 November 2012
Accepted 26 January 2013
Online 2 February 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.003 Å
R = 0.036
wR = 0.103
Data-to-parameter ratio = 12.6
Details
Open access

1-Phenyl-2-p-tolyl-1H-benzimidazole

aShri Angalamman College of Engineering and Technology, Siruganoor, Trichirappalli, Tamilnadu 621 105, India,bAnnamalai University, Chidambaram, Tamilnadu, India, and cDepartment of Physics, Urumu Dhanalakshmi college, Trichirappalli, Tamilnadu 620 019, India
Correspondence e-mail: sakthi2udc@gmail.com

In the title compound, C20H16N2, the benzimidazole ring system forms dihedral angles of 28.50 (7) and 72.44 (7)° with the tolyl and phenyl rings, respectively. In the crystal, molecules are linked into chains along the a-axis direction by weak C-H...N interactions. The crystal structure also features C-H...[pi] interactions.

Related literature

For applications of benzimidazole derivatives, see: Fang et al. (2007[Fang, Z., Wang, S., Zhao, L., Xu, Z., Ren, J. & Wang, X. (2007). Mater. Lett. 61, 4803-4807.]); Ge et al. (2008[Ge, Z., Hayakawa, T., Ando, S., Ueda, M., Akiike, T., Miyamoto, H., Kajita, T. & Kakimoto, M.-A. (2008). Chem. Mater. 20, 2532-2537.]); Lai et al. (2008[Lai, M.-Y., Chen, C.-H., Huang, W.-S., Lin, J. T., Ke, T.-H., Chen, L.-Y., Tsai, M.-H. & Wu, C.-C. (2008). Angew. Chem. Int. Ed. 47, 581-585.]); Shin et al. (2007[Shin, R. Y. C., Kietzke, T., Sudhakar, S., Dodabalapur, A., Chen, Z. K. & Sellinger, A. (2007). Chem. Mater. 19, 1892-1894.]). For their biological activity, see: Garuti et al. (1999[Garuti, L., Roberti, M. & Cermelli, C. (1999). Bioorg. Med. Chem. Lett. 9, 2525-2530.]); Matsuno et al. (2000[Matsuno, T., Kato, M., Sasahara, H., Watanabe, T., Inaba, M., Takahashi, M., Yaguchi, S. I., Yoshioka, K., Sakato, M. & Kawashima, S. (2000). Chem. Pharm. Bull. 48, 1778-1781.]) and for their therapeutic applications, see: Can-Eke et al. (1998[Can-Eke, B., Puskullu, M. O., Buyukbingol, E. & Iscan, M. (1998). Chem. Biol. Interact. 113, 65-67.]); Richter (1997[Richter, J. E. (1997). Am. J. Gastroenterol. 92, 34-34.]). For standard bond lengths, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Talor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]).

[Scheme 1]

Experimental

Crystal data
  • C20H16N2

  • Mr = 284.35

  • Orthorhombic, P b c a

  • a = 15.6755 (4) Å

  • b = 9.3509 (6) Å

  • c = 21.1976 (8) Å

  • V = 3107.1 (2) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 0.07 mm-1

  • T = 293 K

  • 0.30 × 0.30 × 0.25 mm

Data collection
  • Bruker Kappa APEXII diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.966, Tmax = 0.997

  • 15284 measured reflections

  • 2523 independent reflections

  • 1840 reflections with I > 2[sigma](I)

  • Rint = 0.034

Refinement
  • R[F2 > 2[sigma](F2)] = 0.036

  • wR(F2) = 0.103

  • S = 1.01

  • 2523 reflections

  • 201 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.12 e Å-3

  • [Delta][rho]min = -0.11 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C15-C20 phenyl ring.

D-H...A D-H H...A D...A D-H...A
C16-H16...N1i 0.93 2.50 3.337 (2) 149
C20-H20...Cg1ii 0.93 2.80 3.707 (2) 166
Symmetry codes: (i) [-x+{\script{1\over 2}}, y+{\script{1\over 2}}, z]; (ii) -x, -y, -z.

Data collection: APEX2 (Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: 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: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: PLATON.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: FY2081 ).


References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Talor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.
Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Can-Eke, B., Puskullu, M. O., Buyukbingol, E. & Iscan, M. (1998). Chem. Biol. Interact. 113, 65-67.  [ISI] [CrossRef] [ChemPort] [PubMed]
Fang, Z., Wang, S., Zhao, L., Xu, Z., Ren, J. & Wang, X. (2007). Mater. Lett. 61, 4803-4807.  [CrossRef] [ChemPort]
Garuti, L., Roberti, M. & Cermelli, C. (1999). Bioorg. Med. Chem. Lett. 9, 2525-2530.  [CrossRef] [PubMed] [ChemPort]
Ge, Z., Hayakawa, T., Ando, S., Ueda, M., Akiike, T., Miyamoto, H., Kajita, T. & Kakimoto, M.-A. (2008). Chem. Mater. 20, 2532-2537.  [ISI] [CrossRef] [ChemPort]
Lai, M.-Y., Chen, C.-H., Huang, W.-S., Lin, J. T., Ke, T.-H., Chen, L.-Y., Tsai, M.-H. & Wu, C.-C. (2008). Angew. Chem. Int. Ed. 47, 581-585.  [ISI] [CrossRef] [ChemPort]
Matsuno, T., Kato, M., Sasahara, H., Watanabe, T., Inaba, M., Takahashi, M., Yaguchi, S. I., Yoshioka, K., Sakato, M. & Kawashima, S. (2000). Chem. Pharm. Bull. 48, 1778-1781.  [CrossRef] [PubMed] [ChemPort]
Richter, J. E. (1997). Am. J. Gastroenterol. 92, 34-34.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Shin, R. Y. C., Kietzke, T., Sudhakar, S., Dodabalapur, A., Chen, Z. K. & Sellinger, A. (2007). Chem. Mater. 19, 1892-1894.  [ISI] [CrossRef] [ChemPort]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]


Acta Cryst (2013). E69, o334  [ doi:10.1107/S160053681300264X ]

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