organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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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

(Received 27 November 2012; accepted 26 January 2013; online 2 February 2013)

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⋯π 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 Kα radiation

  • μ = 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 > 2σ(I)

  • Rint = 0.034

Refinement
  • R[F2 > 2σ(F2)] = 0.036

  • wR(F2) = 0.103

  • S = 1.01

  • 2523 reflections

  • 201 parameters

  • H-atom parameters constrained

  • Δρmax = 0.12 e Å−3

  • Δρmin = −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 DA 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.

Supporting information


References

First citationAllen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Talor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19.  CrossRef
First citationBruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
First citationCan-Eke, B., Puskullu, M. O., Buyukbingol, E. & Iscan, M. (1998). Chem. Biol. Interact. 113, 65–67.  Web of Science CrossRef CAS PubMed
First citationFang, Z., Wang, S., Zhao, L., Xu, Z., Ren, J. & Wang, X. (2007). Mater. Lett. 61, 4803–4807.  Web of Science CrossRef CAS
First citationGaruti, L., Roberti, M. & Cermelli, C. (1999). Bioorg. Med. Chem. Lett. 9, 2525–2530.  Web of Science CrossRef PubMed CAS
First citationGe, Z., Hayakawa, T., Ando, S., Ueda, M., Akiike, T., Miyamoto, H., Kajita, T. & Kakimoto, M.-A. (2008). Chem. Mater. 20, 2532–2537.  Web of Science CrossRef CAS
First citationLai, 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.  Web of Science CrossRef CAS
First citationMatsuno, 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 CAS
First citationRichter, J. E. (1997). Am. J. Gastroenterol. 92, 34–34.
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals
First citationShin, R. Y. C., Kietzke, T., Sudhakar, S., Dodabalapur, A., Chen, Z. K. & Sellinger, A. (2007). Chem. Mater. 19, 1892–1894.  Web of Science CrossRef CAS
First citationSpek, A. L. (2009). Acta Cryst. D65, 148–155.  Web of Science CrossRef CAS IUCr Journals

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