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

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

doi:10.1107/S1600536812049859

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 (C-C) = 0.003 Å
R = 0.059
wR = 0.171
Data-to-parameter ratio = 13.9
Details

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

A. Thiruvalluvar,^a ^* S. Rosepriya,^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, 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-HN hydrogen bond generates an S(6) ring motif. In the crystal, molecules are linked by C-HN and C-HO 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). For closely related crystal structures, see: Jayamoorthy et al. (2012); Rosepriya et al. (2012). For hydrogen-bond motifs, see: Bernstein et al. (1995).

Experimental

Crystal data

C₁₉H₁₄N₂O
M_r = 286.32
Triclinic, $[P \overline 1]$
a = 8.1941 (6) Å
b = 9.5983 (14) Å
c = 10.3193 (18) Å
= 64.637 (16)°
= 80.356 (10)°
= 83.610 (9)°
V = 722.3 (2) Å³
Z = 2
Cu K radiation
= 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), using a multi-faceted crystal model (Clark & Reid, 1995)] T_min = 0.731, T_max = 0.811
4335 measured reflections
2826 independent reflections
2420 reflections with I > 2(I)
R_int = 0.076

Refinement

R[F² > 2(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
_max = 0.32 e Å^-3
_min = -0.31 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O26-H26N3	0.97 (3)	1.70 (3)	2.583 (2)	150 (3)
C14-H14N3ⁱ	0.95	2.60	3.456 (3)	151
C16-H16O26ⁱⁱ	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); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS86 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) 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: 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.
Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.
Jayamoorthy, K., Rosepriya, S., Thiruvalluvar, A., Jayabharathi, J. & Butcher, R. J. (2012). Acta Cryst. E68, o2708.
Rosepriya, S., Thiruvalluvar, A., Jayamoorthy, K., Jayabharathi, J., Öztürk Yildirim, S. & Butcher, R. J. (2012). Acta Cryst. E68, o3283.
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.

organic compounds

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

Related literature

Experimental

Crystal data

Data collection

Refinement

Acknowledgements

References