Received 4 December 2013
aResearch and Development Center, Bharathiar University, Coimbatore 641 046, Tamilnadu, India,bDepartment of Chemistry, S.K.P. Engineering College, Thiruvannamalai 606 611, Tamilnadu, India,cPostgraduate Research Department of Physics, Rajah Serfoji Government College (Autonomous), Thanjavur 613 005, Tamilnadu, India,dDepartment of Chemistry, Annamaliar College of Engineering, Mudaiyur 606 902, Tamilnadu, India, and eDepartment of Chemistry, Howard University, 525 College Street NW, Washington, DC 20059, USA
Correspondence e-mail: email@example.com
In the title compound, C23H16N2·0.5C6H6, the benzimidazole unit [maximum deviation = 0.0258 (6) Å] and the naphthalene ring system [maximum deviation = 0.0254 (6) Å] are both essentially planar and make a dihedral angle of 61.955 (17)°. The imidazole ring makes dihedral angle of 61.73 (4)° with the phenyl ring. An intramolecular C-HN hydrogen bond generates an S(6) ring motif. In the crystal, seven weak C-H interactions involving the fused ring system, the benzene solvent molecule, the imidazole phenyl rings are observed, leading to a three-dimensional architecture.
For linear and non-linear optical properties and the thermal stability of benzimidazole-based chromophores, see: Cross et al. (1995). For imidazole as a component of vitamin B12, purine and caffeine, see: Brown (2005). For commercial and therapeutic applications of substituted benzimidazole derivatives, see: Spasov et al. (1999). For related crystal structures, see: Jayamoorthy et al. (2012, 2013); Rosepriya et al. (2011). For hydrogen-bond motifs, see: Bernstein et al. (1995).
Data collection: CrysAlis PRO (Agilent, 2012); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS2013 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and PLATON (Spek, 2009); software used to prepare material for publication: SHELXL2013 and PLATON (Spek, 2009).
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: JJ2179 ).
SMP thanks Annamaliar College of Engineering, Mudaiyur, for providing constant support for this research. RJB acknowledges the NSF-MRI program (grant No. CHE-0619278) for funds to purchase an X-ray diffractometer.
Agilent (2012). CrysAlis PRO. Agilent Technologies, Yarnton, England.
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.
Brown, K. L. (2005). Chem. Rev. 105, 2075-2150.
Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897.
Cross, E. M., White, K. M., Moshrefzadeh, R. S. & Francis, C. V. (1995). Macromolecules, 28, 2526-2532.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.
Jayamoorthy, K., Mohandas, T., Sakthivel, P. & Jayabharathi, J. (2013). Acta Cryst. E69, o244.
Jayamoorthy, K., Rosepriya, S., Thiruvalluvar, A., Jayabharathi, J. & Butcher, R. J. (2012). Acta Cryst. E68, o2708.
Rosepriya, S., Thiruvalluvar, A., Jayamoorthy, K., Jayabharathi, J. & Linden, A. (2011). Acta Cryst. E67, o3519.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spasov, A. A., Yozhitsa, I. N., Bugaeva, L. I. & Anisimova, V. A. (1999). Pharm. Chem. J. 33, 232-243.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.