2-(1H-Benzimidazol-2-yl)-4,6-dichloro­phenol

Han, L.-L.

doi:10.1107/S1600536810027844

Volume 66
Part 8
Page o2047
August 2010

Received 1 July 2010
Accepted 13 July 2010
Online 17 July 2010

Key indicators
Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.003 Å
R = 0.042
wR = 0.127
Data-to-parameter ratio = 15.3
Details

2-(1H-Benzimidazol-2-yl)-4,6-dichlorophenol

Li-Lu Han ^a ^*

^aHunan Yongzhou Vocational College, Yongzhou Hunan 425100, People's Republic of China
Correspondence e-mail: yzzyhll@126.com

The title compound, C₁₃H₈Cl₂N₂O, was prepared by the reaction of 3,5-dichloro-2-hydroxybenzaldehyde with 1,2-diaminobenzene in methanol at ambient temperature. The title molecule is essentially planar, the mean deviation from the plane of the non-H atoms being 0.037 (2) Å. There is an intramolecular O-HN hydrogen bond in the molecule. In the crystal, symmetry-related molecules are linked through N-HO hydrogen bonds, forming polymeric chains propagating in [001]. The chains are linked by [pi] - [pi] interactions involving the dichlorophenol ring and the benzoimidazole ring system [centroid-centroid distances = 3.535 (2) and 3.724 (2) Å].

Related literature

For the preparation and crystal structures of some Schiff bases bearing a C=N double bond, see: Jeseentharani et al. (2010); Hamaker et al. (2010); Tanaka et al. (2010); Tunç et al. (2009); Khalaji et al. (2010). For standard bond distances, see: Allen et al. (1987).

Experimental

Crystal data

C₁₃H₈Cl₂N₂O
M_r = 279.11
Monoclinic, P 2₁ /c
a = 11.850 (3) Å
b = 7.446 (3) Å
c = 13.947 (2) Å
= 104.261 (3)°
V = 1192.7 (6) Å³
Z = 4
Mo K radiation
= 0.53 mm^-1
T = 298 K
0.21 × 0.20 × 0.18 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001) T_min = 0.897, T_max = 0.911
6117 measured reflections
2562 independent reflections
1810 reflections with I > 2(I)
R_int = 0.035

Refinement

R[F² > 2(F²)] = 0.042
wR(F²) = 0.127
S = 1.03
2562 reflections
167 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
_max = 0.26 e Å^-3
_min = -0.23 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O1-H1N2	0.82	1.85	2.582 (2)	148
N1-H1AO1ⁱ	0.90 (3)	2.39 (2)	3.145 (2)	143 (3)
Symmetry code: (i) $[x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SU2193 ).

Acknowledgements

The author acknowledges Hunan Yongzhou Vocational College for supporting this work.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.
Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Hamaker, C. G., Maryashina, O. S., Daley, D. K. & Wadler, A. L. (2010). J. Chem. Crystallogr. 40, 34-39.
Jeseentharani, V., Selvakumar, J., Dayalan, A., Varghese, B. & Nagaraja, K. S. (2010). J. Mol. Struct. 966, 122-128.
Khalaji, A. D., Chermahini, A. N., Fejfarova, K. & Dusek, M. (2010). Struct. Chem. 21, 153-157.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Tanaka, K., Shimoura, R. & Caira, M. R. (2010). Tetrahedron Lett. 51, 449-452.
Tunç, T., Sari, M., Sadikoglu, M. & Büyükgüngör, O. (2009). J. Chem. Crystallogr. 39, 672-676.

organic compounds