1,2-Diphenyl-1H-benzimidazole

Rosepriya, S.; Thiruvalluvar, A.; Jayamoorthy, K.; Jayabharathi, J.; Öztürk Yildirim, S.; Butcher, R.J.

doi:10.1107/S1600536812044960

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 (C-C) = 0.001 Å
R = 0.052
wR = 0.137
Data-to-parameter ratio = 38.4
Details

1,2-Diphenyl-1H-benzimidazole

S. Rosepriya,^a A. Thiruvalluvar,^a ^* K. Jayamoorthy,^b J. Jayabharathi,^b Sema Öztürk Yildirim ^c,^d and R. J. Butcher ^c

^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-HN 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); Ge et al. (2008); Lai et al. (2008); Shin et al. (2007); Tsai et al. (2007). For a closely related crystal structure, see: Jayamoorthy et al. (2012).

Experimental

Crystal data

C₁₉H₁₄N₂
M_r = 270.32
Monoclinic, C 2/c
a = 10.1878 (3) Å
b = 16.6399 (4) Å
c = 17.4959 (5) Å
= 106.205 (3)°
V = 2848.13 (14) Å³
Z = 8
Mo K radiation
= 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) T_min = 0.957, T_max = 0.974
25253 measured reflections
7296 independent reflections
5803 reflections with I > 2(I)
R_int = 0.028

Refinement

R[F² > 2(F²)] = 0.052
wR(F²) = 0.137
S = 1.06
7296 reflections
190 parameters
H-atom parameters constrained
_max = 0.52 e Å^-3
_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-HA	D-H	HA	DA	D-HA
C14-H14N3ⁱ	0.93	2.62	3.4829 (11)	154
C16-H16Cg2ⁱⁱ	0.93	2.68	3.4843 (9)	146
C22-H22Cg1ⁱⁱⁱ	0.93	2.91	3.3966 (9)	114
C23-H23Cg2ⁱⁱⁱ	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); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2009); 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.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Ge, Z., Hayakawa, T., Ando, S., Ueda, M., Akiike, T., Miyamoto, H., Kajita, T. & Kakimoto, M.-A. (2008). Chem. Mater. 20, 2532-2537.
Jayamoorthy, K., Rosepriya, S., Thiruvalluvar, A., Jayabharathi, J. & Butcher, R. J. (2012). Acta Cryst. E68, o2708.
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.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Shin, R. Y. C., Kietzke, T., Sudhakar, S., Dodabalapur, A., Chen, Z.-K. & Sellinger, A. (2007). Chem. Mater. 19, 1892-1894.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.
Tsai, M.-S., Hsu, Y.-C., Lin, J. T., Chen, H.-C. & Hsu, C.-P. (2007). J. Phys. Chem. C. 111, 18785-18793.

organic compounds

1,2-Diphenyl-1H-benzimidazole

Related literature

Experimental

Crystal data

Data collection

Refinement

Acknowledgements

References