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Volume 65 
Part 1 
Page o85  
January 2009  

Received 1 December 2008
Accepted 7 December 2008
Online 10 December 2008

Key indicators
Single-crystal X-ray study
T = 298 K
Mean [sigma](C-C) = 0.004 Å
R = 0.036
wR = 0.075
Data-to-parameter ratio = 16.6
Details
Open access

3-Bromo-N'-(3,5-dichloro-2-hydroxybenzylidene)benzohydrazide

aDepartment of Chemistry, Huainan Normal College, Huainan 232001, People's Republic of China
Correspondence e-mail: huainanweiyijun@163.com

The title compound, C14H9BrCl2N2O2, was prepared by the reaction of 3,5-dichloro-2-hydroxybenzaldehyde and 3-bromobenzohydrazide in methanol. The dihedral angle between the two benzene rings is 13.0 (2)°. An intramolecular O-H...N hydrogen bond is observed. The molecules are linked into chains along the c axis by intermolecular N-H...O hydrogen bonds.

Related literature

For the synthesis of Schiff bases, see: Akitsu & Einaga (2006[Akitsu, T. & Einaga, Y. (2006). Acta Cryst. E62, o4315-o4317.]); Butcher et al. (2005[Butcher, R. J., Basu Baul, T. S., Singh, K. S. & Smith, F. E. (2005). Acta Cryst. E61, o1007-o1009.]); Habibi et al. (2007[Habibi, M. H., Mokhtari, R., Harrington, R. W. & Clegg, W. (2007). Acta Cryst. E63, o2881.]); Pradeep (2005[Pradeep, C. P. (2005). Acta Cryst. E61, o3825-o3827.]). For related structures, see: Bao & Wei (2008[Bao, X. & Wei, Y.-J. (2008). Acta Cryst. E64, o1682.]); Odabasoglu et al. (2007[Odabasoglu, M., Büyükgüngör, O., Narayana, B., Vijesh, A. M. & Yathirajan, H. S. (2007). Acta Cryst. E63, o1916-o1918.]); Wang et al. (2006[Wang, F.-W., Wei, Y.-J. & Zhu, Q.-Y. (2006). Chin. J. Struct. Chem. 25, 1179-1182.]); Wei et al. (2008[Wei, Y.-J., Wang, F.-W. & Zhu, Q.-Y. (2008). Transition Met. Chem. 33, 543-546.]); Yathirajan et al. (2007[Yathirajan, H. S., Vijesh, A. M., Narayana, B., Sarojini, B. K. & Bolte, M. (2007). Acta Cryst. E63, o936-o938.]); Yehye et al. (2008[Yehye, W. A., Ariffin, A. & Ng, S. W. (2008). Acta Cryst. E64, o1452.]); Zhu et al. (2007[Zhu, C.-G., Wei, Y.-J. & Wang, F.-W. (2007). Acta Cryst. E63, m3197-m3198.]).

[Scheme 1]

Experimental

Crystal data
  • C14H9BrCl2N2O2

  • Mr = 388.04

  • Monoclinic, P 21 /c

  • a = 8.272 (2) Å

  • b = 22.366 (3) Å

  • c = 8.237 (2) Å

  • [beta] = 104.014 (2)°

  • V = 1478.6 (5) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 3.15 mm-1

  • T = 298 (2) K

  • 0.23 × 0.23 × 0.22 mm

Data collection
  • Bruker SMART 1000 CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.495, Tmax = 0.513

  • 8590 measured reflections

  • 3224 independent reflections

  • 2144 reflections with I > 2[sigma](I)

  • Rint = 0.035

Refinement
  • R[F2 > 2[sigma](F2)] = 0.036

  • wR(F2) = 0.075

  • S = 0.98

  • 3224 reflections

  • 194 parameters

  • 1 restraint

  • H atoms treated by a mixture of independent and constrained refinement

  • [Delta][rho]max = 0.32 e Å-3

  • [Delta][rho]min = -0.29 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 1.88 2.598 (3) 145
N2-H2...O2i 0.89 (1) 2.03 (1) 2.898 (3) 165 (3)
Symmetry code: (i) [x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}].

Data collection: SMART (Bruker, 2002[Bruker (2002). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2002[Bruker (2002). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, 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: 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: CI2740 ).


Acknowledgements

The authors thank the Natural Science Foundation of the Education Office of Anhui Province, China, for financial support (grant No. KJ2007A126ZC).

References

Akitsu, T. & Einaga, Y. (2006). Acta Cryst. E62, o4315-o4317.  [CSD] [CrossRef] [details]
Bao, X. & Wei, Y.-J. (2008). Acta Cryst. E64, o1682.  [CSD] [CrossRef] [details]
Bruker (2002). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Butcher, R. J., Basu Baul, T. S., Singh, K. S. & Smith, F. E. (2005). Acta Cryst. E61, o1007-o1009.  [CrossRef] [details]
Habibi, M. H., Mokhtari, R., Harrington, R. W. & Clegg, W. (2007). Acta Cryst. E63, o2881.  [CSD] [CrossRef] [details]
Odabasoglu, M., Büyükgüngör, O., Narayana, B., Vijesh, A. M. & Yathirajan, H. S. (2007). Acta Cryst. E63, o1916-o1918.  [CSD] [CrossRef] [details]
Pradeep, C. P. (2005). Acta Cryst. E61, o3825-o3827.  [CSD] [CrossRef] [details]
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Wang, F.-W., Wei, Y.-J. & Zhu, Q.-Y. (2006). Chin. J. Struct. Chem. 25, 1179-1182.  [ChemPort]
Wei, Y.-J., Wang, F.-W. & Zhu, Q.-Y. (2008). Transition Met. Chem. 33, 543-546.  [ISI] [CrossRef] [ChemPort]
Yathirajan, H. S., Vijesh, A. M., Narayana, B., Sarojini, B. K. & Bolte, M. (2007). Acta Cryst. E63, o936-o938.  [CSD] [CrossRef] [details]
Yehye, W. A., Ariffin, A. & Ng, S. W. (2008). Acta Cryst. E64, o1452.  [CSD] [CrossRef] [details]
Zhu, C.-G., Wei, Y.-J. & Wang, F.-W. (2007). Acta Cryst. E63, m3197-m3198.  [CSD] [CrossRef] [details]


Acta Cryst (2009). E65, o85  [ doi:10.1107/S1600536808041378 ]

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