3-Chloro-N′-(2-chloro­benzyl­idene)benzohydrazide

Lei, Y.; Fu, C.

doi:10.1107/S1600536811001656

Volume 67
Part 2
Page o410
February 2011

Received 8 January 2011
Accepted 11 January 2011
Online 15 January 2011

Key indicators
Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.003 Å
R = 0.048
wR = 0.130
Data-to-parameter ratio = 16.9
Details

3-Chloro-N'-(2-chlorobenzylidene)benzohydrazide

Yan Lei ^a ^* and Chuan Fu ^a

^aSchool of Chemistry & Environmental Engineering, Chongqing Three Gorges University, Chongqing 404000, People's Republic of China
Correspondence e-mail: leiyan222@yahoo.cn

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.

Related literature

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).

Experimental

Crystal data

C₁₄H₁₀Cl₂N₂O
M_r = 293.14
Monoclinic, P 2₁ /c
a = 13.106 (3) Å
b = 12.588 (3) Å
c = 8.347 (2) Å
= 97.578 (2)°
V = 1365.0 (6) Å³
Z = 4
Mo K radiation
= 0.47 mm^-1
T = 298 K
0.32 × 0.30 × 0.30 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2000) T_min = 0.865, T_max = 0.873
6893 measured reflections
2954 independent reflections
1936 reflections with I > 2(I)
R_int = 0.032

Refinement

R[F² > 2(F²)] = 0.048
wR(F²) = 0.130
S = 1.01
2954 reflections
175 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
_max = 0.26 e Å^-3
_min = -0.48 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N2-H2O1ⁱ	0.90 (1)	1.98 (1)	2.854 (2)	164 (2)
C7-H7O1ⁱ	0.93	2.51	3.254 (2)	137 (2)
Symmetry code: (i) $[x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ .

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 ).

Acknowledgements

The authors acknowledge financial support from the Chongqing Three Gorges University.

References

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.

organic compounds