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Volume 68 
Part 12 
Page o3283  
December 2012  

Received 27 October 2012
Accepted 30 October 2012
Online 3 November 2012

Key indicators
Single-crystal X-ray study
T = 123 K
Mean [sigma](C-C) = 0.001 Å
R = 0.052
wR = 0.137
Data-to-parameter ratio = 38.4
Details
Open access

1,2-Diphenyl-1H-benzimidazole

aPostgraduate Research Department of Physics, Rajah Serfoji Government College (Autonomous), Thanjavur 613 005, Tamilnadu, India,bDepartment of Chemistry, Annamalai University, Annamalai Nagar 608 002, Tamilnadu, India,cDepartment of Chemistry, Howard University, 525 College Street NW, Washington, DC 20059, USA, and dDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey
Correspondence e-mail: thiruvalluvar.a@gmail.com

In the title molecule, C19H14N2, the benzimidazole unit is close to being planar [maximum deviation = 0.0102 (6) Å] and forms dihedral angles of 55.80 (2) and 40.67 (3)° with the adjacent phenyl rings; the dihedral angle between the phenyl rings is 62.37 (3)°. In the crystal, one C-H...N hydrogen bond and three weak C-H...[pi] interactions involving the fused benzene ring and the imidazole ring are observed, leading to a three-dimensional architecture.

Related literature

For the use of benzoimidazoles and phenanthroimidazoles as light-emitting devices and dye-sensitized solar cells, see: Fang et al. (2007[Fang, Z., Wang, S., Zhao, L., Xu, Z., Ren, J., Wang, X. & Yang, Q. (2007). Mater. Lett. 61, 4803-4806.]); 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.]); Tsai et al. (2007[Tsai, M.-S., Hsu, Y.-C., Lin, J. T., Chen, H.-C. & Hsu, C.-P. (2007). J. Phys. Chem. C. 111, 18785-18793.]). For a closely related crystal structure, see: Jayamoorthy et al. (2012[Jayamoorthy, K., Rosepriya, S., Thiruvalluvar, A., Jayabharathi, J. & Butcher, R. J. (2012). Acta Cryst. E68, o2708.]).

[Scheme 1]

Experimental

Crystal data
  • C19H14N2

  • Mr = 270.32

  • Monoclinic, C 2/c

  • a = 10.1878 (3) Å

  • b = 16.6399 (4) Å

  • c = 17.4959 (5) Å

  • [beta] = 106.205 (3)°

  • V = 2848.13 (14) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 0.08 mm-1

  • T = 123 K

  • 0.60 × 0.40 × 0.35 mm

Data collection
  • Agilent Xcalibur Ruby Gemini diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012[Agilent (2012). CrysAlis PRO. Agilent Technologies, Yarnton, England.]) Tmin = 0.957, Tmax = 0.974

  • 25253 measured reflections

  • 7296 independent reflections

  • 5803 reflections with I > 2[sigma](I)

  • Rint = 0.028

Refinement
  • R[F2 > 2[sigma](F2)] = 0.052

  • wR(F2) = 0.137

  • S = 1.06

  • 7296 reflections

  • 190 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.52 e Å-3

  • [Delta][rho]min = -0.25 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg2 is the centroid of the C4-C9 fused benzene ring and Cg1 is the centroid of the N1/C2/N3/C9/C8 imidazole ring.

D-H...A D-H H...A D...A D-H...A
C14-H14...N3i 0.93 2.62 3.4829 (11) 154
C16-H16...Cg2ii 0.93 2.68 3.4843 (9) 146
C22-H22...Cg1iii 0.93 2.91 3.3966 (9) 114
C23-H23...Cg2iii 0.93 2.83 3.4609 (9) 126
Symmetry codes: (i) [x+{\script{1\over 2}}, y-{\script{1\over 2}}, z]; (ii) [-x, y, -z+{\script{1\over 2}}]; (iii) -x, -y+1, -z.

Data collection: CrysAlis PRO (Agilent, 2012[Agilent (2012). CrysAlis PRO. Agilent Technologies, Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]) and 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: HG5265 ).


Acknowledgements

KJ thanks the DST (No. SR/S1/IC-73/2010) for a fellowship. JJ thanks the DST (No. SR/S1/IC-73/2010), the UGC [F. No. 36-21/2008 (SR)] and the DRDO (NRB-213/MAT/10-11) for providing funds for this research study. RJB acknowledges the NSF MRI program (grant No. CHE-0619278) for funds to purchase an X-ray diffractometer.

References

Agilent (2012). CrysAlis PRO. Agilent Technologies, Yarnton, England.
Fang, Z., Wang, S., Zhao, L., Xu, Z., Ren, J., Wang, X. & Yang, Q. (2007). Mater. Lett. 61, 4803-4806.  [CrossRef] [ChemPort]
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  [CrossRef] [details]
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]
Jayamoorthy, K., Rosepriya, S., Thiruvalluvar, A., Jayabharathi, J. & Butcher, R. J. (2012). Acta Cryst. E68, o2708.  [CSD] [CrossRef] [details]
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]
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]
Tsai, M.-S., Hsu, Y.-C., Lin, J. T., Chen, H.-C. & Hsu, C.-P. (2007). J. Phys. Chem. C. 111, 18785-18793.  [CrossRef] [ChemPort]


Acta Cryst (2012). E68, o3283  [ doi:10.1107/S1600536812044960 ]

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