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Volume 69 
Part 1 
Page o62  
January 2013  

Received 4 December 2012
Accepted 5 December 2012
Online 8 December 2012

Key indicators
Single-crystal X-ray study
T = 123 K
Mean [sigma](C-C) = 0.003 Å
R = 0.059
wR = 0.171
Data-to-parameter ratio = 13.9
Details
Open access

2-(1-Phenyl-1H-benzimidazol-2-yl)phenol

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, C19H14N2O, the benzimidazole unit is close to being planar [maximum deviation = 0.0253 (11) Å] and forms dihedral angles of 68.98 (6) and 20.38 (7)° with the adjacent phenyl and benzene rings; the dihedral angle between the latter two planes is 64.30 (7)°. An intramolecular O-H...N hydrogen bond generates an S(6) ring motif. In the crystal, molecules are linked by C-H...N and C-H...O hydrogen bonds, and consolidated into a three-dimensional architecture by [pi]-[pi] stacking interactions, with a centroid-centroid distance of 3.8428 (12) Å.

Related literature

For the range of pharmacological activities and toxicological properties of benzimidazole derivatives, see: Spasov et al. (1999[Spasov, A. A., Yozhitsa, I. N., Bugaeva, L. I. & Anisimova, V. A. (1999). Pharm. Chem. J. 33, 232-243.]). For closely related crystal structures, see: Jayamoorthy et al. (2012[Jayamoorthy, K., Rosepriya, S., Thiruvalluvar, A., Jayabharathi, J. & Butcher, R. J. (2012). Acta Cryst. E68, o2708.]); Rosepriya et al. (2012[Rosepriya, S., Thiruvalluvar, A., Jayamoorthy, K., Jayabharathi, J., Öztürk Yildirim, S. & Butcher, R. J. (2012). Acta Cryst. E68, o3283.]). For hydrogen-bond motifs, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]).

[Scheme 1]

Experimental

Crystal data
  • C19H14N2O

  • Mr = 286.32

  • Triclinic, [P \overline 1]

  • a = 8.1941 (6) Å

  • b = 9.5983 (14) Å

  • c = 10.3193 (18) Å

  • [alpha] = 64.637 (16)°

  • [beta] = 80.356 (10)°

  • [gamma] = 83.610 (9)°

  • V = 722.3 (2) Å3

  • Z = 2

  • Cu K[alpha] radiation

  • [mu] = 0.66 mm-1

  • T = 123 K

  • 0.76 × 0.46 × 0.32 mm

Data collection
  • Agilent Xcalibur Ruby Gemini diffractometer

  • Absorption correction: analytical [CrysAlis PRO (Agilent, 2012[Agilent (2012). CrysAlis PRO. Agilent Technologies, Yarnton, England.]), using a multi-faceted crystal model (Clark & Reid, 1995[Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897.])] Tmin = 0.731, Tmax = 0.811

  • 4335 measured reflections

  • 2826 independent reflections

  • 2420 reflections with I > 2[sigma](I)

  • Rint = 0.076

Refinement
  • R[F2 > 2[sigma](F2)] = 0.059

  • wR(F2) = 0.171

  • S = 1.04

  • 2826 reflections

  • 203 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • [Delta][rho]max = 0.32 e Å-3

  • [Delta][rho]min = -0.31 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O26-H26...N3 0.97 (3) 1.70 (3) 2.583 (2) 150 (3)
C14-H14...N3i 0.95 2.60 3.456 (3) 151
C16-H16...O26ii 0.95 2.49 3.388 (2) 157
Symmetry codes: (i) x, y+1, z; (ii) -x+1, -y, -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: SHELXS86 (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 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) 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: TK5179 ).


Acknowledgements

KJ thanks the DST (No. SRS1IC-73/2010) for a fellowship. JJ thanks the DST (No. SRSIC-73/2010), the UGC [F. No. 36-21/2008 (SR)] and the DRDO (NRB-213/MAT/10-11) for providing funds for this research. 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.
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.  [CrossRef] [ChemPort] [ISI]
Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897.  [CrossRef] [details]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Jayamoorthy, K., Rosepriya, S., Thiruvalluvar, A., Jayabharathi, J. & Butcher, R. J. (2012). Acta Cryst. E68, o2708.  [CSD] [CrossRef] [details]
Rosepriya, S., Thiruvalluvar, A., Jayamoorthy, K., Jayabharathi, J., Öztürk Yildirim, S. & Butcher, R. J. (2012). Acta Cryst. E68, o3283.  [CSD] [CrossRef] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spasov, A. A., Yozhitsa, I. N., Bugaeva, L. I. & Anisimova, V. A. (1999). Pharm. Chem. J. 33, 232-243.  [CrossRef] [ChemPort]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]


Acta Cryst (2013). E69, o62  [ doi:10.1107/S1600536812049859 ]

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