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Volume 69 
Part 5 
Page o700  
May 2013  

Received 23 March 2013
Accepted 7 April 2013
Online 13 April 2013

Key indicators
Single-crystal X-ray study
T = 291 K
Mean [sigma](C-C) = 0.002 Å
R = 0.047
wR = 0.119
Data-to-parameter ratio = 14.4
Details
Open access

2-{[2-(Pyridin-4-yl)-1H-benzimidazol-1-yl]methyl}phenol

aCollege of Chemistry and Chemical Engineering, Northwest Normal University, Lanzhou 730070, People's Republic of China, and bDepartment of Chemistry, Faculty of Education, University of Khartoum, Sudan
Correspondence e-mail: jcliu8@nwnu.edu.cn

In the title compound, C19H15N3O, the benzimidazole ring system makes dihedral angles of 44.36 (7) and 75.67 (7)° with the pyridine and benzene rings, respectively. In the crystal, phenolic O-H...N hydrogen bonds to benzimidazole N-atom acceptors give rise to a chain extending along [011].

Related literature

For applications of benzimidazole derivatives as ligands, see: Janiak (2000[Janiak, C. (2000). Dalton Trans. 21, 3885-3896.]); Kühler et al. (2002[Kühler, T. C., Swanson, M., Christenson, B., Klintenberg, A.-C., Lamm, B., Fägherhag, J., Gatti, R., Ölwegård-Halvarsson, M., Shcherbuchin, V., Elebring, T. & Sjöström, J.-E. (2002). J. Med. Chem. 45, 4282-4299.]); Li et al. (2007[Li, X.-P., Pan, M., Zheng, S.-R., Liu, Y.-R., He, Q.-T., Kang, B.-S. & Su, C.-Y. (2007). Cryst. Growth Des. 7, 1569-1574.]); Carcanague et al. (2002[Carcanague, D., Shue, Y.-K., Wuonola, M. A., Uria-Nickelsen, M., Joubran, C., Abedi, J. K., Jones, J. & Kühler, T. C. (2002). J. Med. Chem. 45, 4300-4309.]); Yang et al. (2006[Yang, X.-P., Jones, R. A., Lai, R. J., Waheed, A., Oye, M. M. & Holmes, A. L. (2006). Polyhedron, 25, 881-887.]). For the synthesis of the title compound, see: Fellah et al. (2010[Fellah, F. Z. C., Costes, J.-P., Duhayon, C., Daran, J.-C. & Tuchagues, J.-P. (2010). Polyhedron, 29, 2111-2119.]). For the structure of a similar compound, see: Kitazume & Ishikawa (1974[Kitazume, T. & Ishikawa, N. (1974). Bull. Chem. Soc. Jpn, 47, 785-786.]).

[Scheme 1]

Experimental

Crystal data
  • C19H15N3O

  • Mr = 301.34

  • Monoclinic, C 2/c

  • a = 16.1886 (7) Å

  • b = 8.4863 (4) Å

  • c = 21.4316 (10) Å

  • [beta] = 93.756 (4)°

  • V = 2938.0 (2) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 0.09 mm-1

  • T = 291 K

  • 0.36 × 0.28 × 0.25 mm

Data collection
  • Agilent SuperNova CCD diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012[Agilent (2012). CrysAlis PRO. Agilent Technologies, Yarnton, England.]) Tmin = 0.982, Tmax = 1.000

  • 6104 measured reflections

  • 3010 independent reflections

  • 2398 reflections with I > 2[sigma](I)

  • Rint = 0.026

Refinement
  • R[F2 > 2[sigma](F2)] = 0.047

  • wR(F2) = 0.119

  • S = 1.06

  • 3010 reflections

  • 209 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.14 e Å-3

  • [Delta][rho]min = -0.19 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O1-H1...N2i 0.82 1.95 2.7659 (18) 177
Symmetry code: (i) [x-{\script{1\over 2}}, y+{\script{1\over 2}}, 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: SUPERFLIP (Palatinus & Chapuis, 2007[Palatinus, L. & Chapuis, G. (2007). J. Appl. Cryst. 40, 786-790.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: OLEX2 (Dolomanov et al., 2009[Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.]); software used to prepare material for publication: OLEX2.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: ZS2254 ).


Acknowledgements

This work was supported by the Natural Science Foundation of Gansu (grant No. 0710RJ ZA113).

References

Agilent (2012). CrysAlis PRO. Agilent Technologies, Yarnton, England.
Carcanague, D., Shue, Y.-K., Wuonola, M. A., Uria-Nickelsen, M., Joubran, C., Abedi, J. K., Jones, J. & Kühler, T. C. (2002). J. Med. Chem. 45, 4300-4309.  [ISI] [CrossRef] [PubMed] [ChemPort]
Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.  [ISI] [CrossRef] [ChemPort] [details]
Fellah, F. Z. C., Costes, J.-P., Duhayon, C., Daran, J.-C. & Tuchagues, J.-P. (2010). Polyhedron, 29, 2111-2119.
Janiak, C. (2000). Dalton Trans. 21, 3885-3896.
Kitazume, T. & Ishikawa, N. (1974). Bull. Chem. Soc. Jpn, 47, 785-786.  [CrossRef] [ChemPort] [ISI]
Kühler, T. C., Swanson, M., Christenson, B., Klintenberg, A.-C., Lamm, B., Fägherhag, J., Gatti, R., Ölwegård-Halvarsson, M., Shcherbuchin, V., Elebring, T. & Sjöström, J.-E. (2002). J. Med. Chem. 45, 4282-4299.  [ISI] [PubMed]
Li, X.-P., Pan, M., Zheng, S.-R., Liu, Y.-R., He, Q.-T., Kang, B.-S. & Su, C.-Y. (2007). Cryst. Growth Des. 7, 1569-1574.  [ChemPort]
Palatinus, L. & Chapuis, G. (2007). J. Appl. Cryst. 40, 786-790.  [ISI] [CrossRef] [ChemPort] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Yang, X.-P., Jones, R. A., Lai, R. J., Waheed, A., Oye, M. M. & Holmes, A. L. (2006). Polyhedron, 25, 881-887.  [ISI] [CSD] [CrossRef] [ChemPort]


Acta Cryst (2013). E69, o700  [ doi:10.1107/S1600536813009458 ]

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