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Volume 69 
Part 3 
Page o362  
March 2013  

Received 23 October 2012
Accepted 21 January 2013
Online 9 February 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.008 Å
R = 0.051
wR = 0.133
Data-to-parameter ratio = 16.3
Details
Open access

2-[(1H-Benzimidazol-2-yl)iminomethyl]-4,6-dibromophenol ethanol hemisolvate

aKey Laboratory of Nonferrous Metal Materials and Processing Technology, Department of Material and Chemical Engineering, Guilin University of Technology, Ministry of Education, Guilin 541004, People's Republic of China
Correspondence e-mail: lisa4.6@163.com

The title compound, C14H9Br2N3O·0.5C2H5OH, crystallizes with two 2-[(1H-benzimidazol-2-yl)iminomethyl]-4,6-dibromophenol molecules and one ethanol solvent molecule in the asymmetric unit. The benzene and benzimidazole rings subtend dihedral angles of 4.5 (3) and 5.2 (2)° in the two molecules. In the crystal, one molecule presents [pi]-[pi] stacking with the equivalent molecule related by inversion, at a distance of 3.30 Å (separation between molecular mean planes). A three-dimensional network is formed through N-H...N, N-H...O and O-H...N hydrogen bonds.

Related literature

For background to benzimidazole compounds, see: Zhang et al. (2008[Zhang, S.-H., Zeng, M.-H. & Liang, H. (2008). J. Coord. Chem. 61, 2422-2427.], 2011[Zhang, S.-H., Ma, L.-F., Zou, H.-H., Wang, Y.-G., Liang, H. & Zeng, M.-H. (2011). Dalton Trans. 40, 11402-11409.]).

[Scheme 1]

Experimental

Crystal data
  • C14H9Br2N3O·0.5C2H6O

  • Mr = 836.19

  • Monoclinic, P 21 /c

  • a = 14.5300 (15) Å

  • b = 16.8190 (14) Å

  • c = 13.8491 (17) Å

  • [beta] = 111.656 (13)°

  • V = 3145.5 (6) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 5.16 mm-1

  • T = 293 K

  • 0.23 × 0.22 × 0.21 mm

Data collection
  • Agilent SuperNova Eos diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011[Agilent (2011). CrysAlis PRO. Agilent Technologies, Yarnton, England.]) Tmin = 0.436, Tmax = 1.000

  • 19465 measured reflections

  • 6390 independent reflections

  • 4189 reflections with I > 2[sigma](I)

  • Rint = 0.051

Refinement
  • R[F2 > 2[sigma](F2)] = 0.051

  • wR(F2) = 0.133

  • S = 1.03

  • 6390 reflections

  • 392 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 1.55 e Å-3

  • [Delta][rho]min = -0.76 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N5-H5...N3 0.86 2.14 2.997 (4) 172
N2-H2A...O3i 0.86 2.00 2.816 (4) 157
O1-H1...N1 0.82 1.90 2.618 (6) 146
O2-H2...N4 0.82 1.92 2.640 (6) 147
O3-H3...N6ii 0.82 2.08 2.900 (5) 176
Symmetry codes: (i) [x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]; (ii) -x+1, -y+1, -z.

Data collection: CrysAlis PRO (Agilent, 2011[Agilent (2011). CrysAlis PRO. Agilent Technologies, Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (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: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BH2461 ).


Acknowledgements

The authors acknowledge financial support by the National Natural Science Foundation of China (No. 2126606).

References

Agilent (2011). CrysAlis PRO. Agilent Technologies, Yarnton, England.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Zhang, S.-H., Ma, L.-F., Zou, H.-H., Wang, Y.-G., Liang, H. & Zeng, M.-H. (2011). Dalton Trans. 40, 11402-11409.  [CSD] [CrossRef] [ChemPort] [PubMed]
Zhang, S.-H., Zeng, M.-H. & Liang, H. (2008). J. Coord. Chem. 61, 2422-2427.  [ChemPort]


Acta Cryst (2013). E69, o362  [ doi:10.1107/S1600536813002031 ]

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