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Volume 69 
Part 7 
Page o1190  
July 2013  

Received 23 June 2013
Accepted 26 June 2013
Online 29 June 2013

Key indicators
Single-crystal X-ray study
T = 295 K
Mean [sigma](C-C) = 0.006 Å
R = 0.038
wR = 0.082
Data-to-parameter ratio = 14.9
Details
Open access

2,4-Dibromo-6-{[(5-chloro-2-methylphenyl)imino]methyl}phenol

aDepartment of Chemistry, Lishui University, Lishui 323000, People's Republic of China
Correspondence e-mail: zhyunfa@163.com

In the molecular structure of the title Schiff base, C14H10Br2ClNO, the chlorophenyl ring and dibromophenol ring are almost coplanar; the dihedral angle between the planes of the two rings is 10.50 (18)°. There is an intramolecular O-H...N hydrogen bond, with an O...N distance of 2.576 (4)Å. The crystal structure is stabilized by [pi]-[pi] stacking of neighbouring aromatic rings along the b-axis direction [centroid-centroid distance = 3.6896 (5) Å].

Related literature

For general background, see: Siddiqui et al. (2006[Siddiqui, H. L., Iqbal, A., Ahmad, S. & Weaver, G. W. (2006). Molecules, 11, 206-211.]); Fukuda et al. (2009[Fukuda, H., Amimoto, K., Koyama, H. & Kawato, T. (2009). Tetrahedron Lett. 50, 5376-5378.]); Elmali & Elerman (1998[Elmali, A. & Elerman, Y. (1998). J. Mol. Struct. 442, 31-37.]); Karakas et al. (2004[Karakas, A., Elmali, A., Ünverc, H. & Svoboda, I. (2004). J. Mol. Struct. 702, 103-110.]); Ebrahimipour et al. (2012[Ebrahimipour, S. Y., Mague, J. T., Akbari, A. & Takjoo, R. (2012). J. Mol. Struct. 1028, 148-155.]). For the similar Schiff base structures, see: Zhou et al. (2009[Zhou, J.-C., Li, N.-X., Zhang, C.-M. & Zhang, Z.-Y. (2009). Acta Cryst. E65, o1949.]); Atalay et al. (2008[Atalay, S., Erdem, T. K., Ersahin, F. & Tinkiliç, N. (2008). Acta Cryst. E64, o92.]).

[Scheme 1]

Experimental

Crystal data
  • C14H10Br2ClNO

  • Mr = 403.48

  • Monoclinic, C 2/c

  • a = 31.603 (5) Å

  • b = 6.1828 (10) Å

  • c = 14.890 (2) Å

  • [beta] = 102.594 (15)°

  • V = 2839.4 (8) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 5.89 mm-1

  • T = 295 K

  • 0.38 × 0.35 × 0.30 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 2003[Sheldrick, G. M. (2003). SADABS. University of Göttingen, Germany.]) Tmin = 0.123, Tmax = 0.171

  • 5369 measured reflections

  • 2600 independent reflections

  • 1839 reflections with I > 2[sigma](I)

  • Rint = 0.035

Refinement
  • R[F2 > 2[sigma](F2)] = 0.038

  • wR(F2) = 0.082

  • S = 1.00

  • 2600 reflections

  • 174 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.41 e Å-3

  • [Delta][rho]min = -0.37 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O1-H1...N1 0.82 1.85 2.576 (4) 147

Data collection: SMART (Bruker, 2004[Bruker (2004). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsn, USA.]); cell refinement: SAINT (Bruker, 2004[Bruker (2004). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsn, USA.]); data reduction: SAINT; 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: ORTEP-3 (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); software used to prepare material for publication: SHELXL97.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: RK2407 ).


Acknowledgements

The author acknowledge Lishui University for financial support.

References

Atalay, S., Erdem, T. K., Ersahin, F. & Tinkiliç, N. (2008). Acta Cryst. E64, o92.  [CrossRef] [IUCr Journals]
Bruker (2004). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsn, USA.
Ebrahimipour, S. Y., Mague, J. T., Akbari, A. & Takjoo, R. (2012). J. Mol. Struct. 1028, 148-155.
Elmali, A. & Elerman, Y. (1998). J. Mol. Struct. 442, 31-37.  [Web of Science] [CrossRef] [ChemPort]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Fukuda, H., Amimoto, K., Koyama, H. & Kawato, T. (2009). Tetrahedron Lett. 50, 5376-5378.  [CrossRef] [ChemPort]
Karakas, A., Elmali, A., Ünverc, H. & Svoboda, I. (2004). J. Mol. Struct. 702, 103-110.  [ChemPort]
Sheldrick, G. M. (2003). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Siddiqui, H. L., Iqbal, A., Ahmad, S. & Weaver, G. W. (2006). Molecules, 11, 206-211.  [CrossRef] [PubMed] [ChemPort]
Zhou, J.-C., Li, N.-X., Zhang, C.-M. & Zhang, Z.-Y. (2009). Acta Cryst. E65, o1949.  [CSD] [CrossRef] [IUCr Journals]


Acta Cryst (2013). E69, o1190  [ doi:10.1107/S1600536813017558 ]

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