Received 8 January 2011
The title compound, C14H10Cl2N2O, was prepared from the reaction of 2-chlorobenzaldehyde with 3-chlorobenzohydrazide in methanol. The molecule adopts an E configuration about the methylidene unit and the two aromatic rings form a dihedral angle of 13.8 (2)°. In the crystal, molecules are linked via intermolecular N-HO and C-HO hydrogen bonds, forming chains along the c axis.
For background to hydrazones, see: El-Asmy et al. (2010); El-Sherif (2009); Singh et al. (2009); El-Tabl et al. (2007); Lei (2011). For structures of hydrazone compounds, see: Qiao et al. (2010); Hussain et al. (2010); Han & Zhao (2010); Ahmad et al. (2010).
Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); 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: QM2001 ).
The authors acknowledge financial support from the Chongqing Three Gorges University.
Ahmad, T., Zia-ur-Rehman, M., Siddiqui, H. L., Mahmud, S. & Parvez, M. (2010). Acta Cryst. E66, o1022.
Bruker (2000). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
El-Asmy, A. A., El-Gammal, O. A., Radwan, H. A. & Ghazy, S. E. (2010). Spectrochim. Acta Part A, 77, 297-303.
El-Sherif, A. A. (2009). Inorg. Chim. Acta, 362, 4991-5000.
El-Tabl, A. S., El-Saied, F. A. & Al-Hakimi, A. N. (2007). Transition Met. Chem. 32, 689-701.
Han, Y.-Y. & Zhao, Q.-R. (2010). Acta Cryst. E66, o1041.
Hussain, A., Shafiq, Z., Tahir, M. N. & Yaqub, M. (2010). Acta Cryst. E66, o1888.
Lei, Y. (2011). Acta Cryst. E67, o162.
Qiao, Y., Ju, X., Gao, Z. & Kong, L. (2010). Acta Cryst. E66, o95.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Singh, V., Katiyar, A. & Singh, S. (2009). J. Coord. Chem. 62, 1336-1346.