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

Zhu, C.-G.; Wei, Y.-J.; Zhu, Q.-Y.

doi:10.1107/S1600536808041378

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 (C-C) = 0.004 Å
R = 0.036
wR = 0.075
Data-to-parameter ratio = 16.6
Details

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

Chuan-Gao Zhu,^a Yi-Jun Wei ^a ^* and Qi-Yong Zhu ^a

^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-HN hydrogen bond is observed. The molecules are linked into chains along the c axis by intermolecular N-HO hydrogen bonds.

Related literature

For the synthesis of Schiff bases, see: Akitsu & Einaga (2006); Butcher et al. (2005); Habibi et al. (2007); Pradeep (2005). For related structures, see: Bao & Wei (2008); Odabasoglu et al. (2007); Wang et al. (2006); Wei et al. (2008); Yathirajan et al. (2007); Yehye et al. (2008); Zhu et al. (2007).

Experimental

Crystal data

C₁₄H₉BrCl₂N₂O₂
M_r = 388.04
Monoclinic, P 2₁ /c
a = 8.272 (2) Å
b = 22.366 (3) Å
c = 8.237 (2) Å
= 104.014 (2)°
V = 1478.6 (5) Å³
Z = 4
Mo K radiation
= 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) T_min = 0.495, T_max = 0.513
8590 measured reflections
3224 independent reflections
2144 reflections with I > 2(I)
R_int = 0.035

Refinement

R[F² > 2(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
_max = 0.32 e Å^-3
_min = -0.29 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O1-H1N1	0.82	1.88	2.598 (3)	145
N2-H2O2ⁱ	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); cell refinement: SAINT (Bruker, 2002); 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: 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.
Bao, X. & Wei, Y.-J. (2008). Acta Cryst. E64, o1682.
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.
Habibi, M. H., Mokhtari, R., Harrington, R. W. & Clegg, W. (2007). Acta Cryst. E63, o2881.
Odabasoglu, M., Büyükgüngör, O., Narayana, B., Vijesh, A. M. & Yathirajan, H. S. (2007). Acta Cryst. E63, o1916-o1918.
Pradeep, C. P. (2005). Acta Cryst. E61, o3825-o3827.
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Wang, F.-W., Wei, Y.-J. & Zhu, Q.-Y. (2006). Chin. J. Struct. Chem. 25, 1179-1182.
Wei, Y.-J., Wang, F.-W. & Zhu, Q.-Y. (2008). Transition Met. Chem. 33, 543-546.
Yathirajan, H. S., Vijesh, A. M., Narayana, B., Sarojini, B. K. & Bolte, M. (2007). Acta Cryst. E63, o936-o938.
Yehye, W. A., Ariffin, A. & Ng, S. W. (2008). Acta Cryst. E64, o1452.
Zhu, C.-G., Wei, Y.-J. & Wang, F.-W. (2007). Acta Cryst. E63, m3197-m3198.

organic compounds