(E)-4-Chloro-N′-(2-chloro­benzyl­idene)benzohydrazide

Cao, G.-B.

doi:10.1107/S1600536809035739

Volume 65
Part 10
Page o2384
October 2009

Received 24 August 2009
Accepted 4 September 2009
Online 9 September 2009

Key indicators
Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.003 Å
R = 0.037
wR = 0.103
Data-to-parameter ratio = 16.3
Details

(E)-4-Chloro-N'-(2-chlorobenzylidene)benzohydrazide

Guo-Biao Cao ^a ^*

^aDepartment of Chemistry, Ankang University, Ankang Shanxi 725000, People's Republic of China
Correspondence e-mail: guobiao_cao@126.com

The title compound, C₁₄H₁₀Cl₂N₂O, was synthesized by the reaction of 2-chlorobenzaldehyde with an equimolar quantity of 4-chlorobenzohydrazide in methanol. The molecule displays an E configuration about the C=N bond. The dihedral angle between the two benzene rings is 8.6 (2)°. In the crystal structure, molecules are linked through intermolecular N-HO hydrogen bonds, forming chains running along the c axis.

Related literature

For examples of the crystal structures of hydrazone compounds, see: Mohd Lair et al. (2009); Fun et al. (2008); Li & Ban (2009); Zhu et al. (2009); Yang (2007); You et al. (2008). For the hydrazone compounds previously reported by our group, see: Qu et al. (2008); Yang et al. (2008), Cao & Lu (2009a,b), Cao (2009a,b).

Experimental

Crystal data

C₁₄H₁₀Cl₂N₂O
M_r = 293.14
Monoclinic, P 2₁ /c
a = 10.9140 (4) Å
b = 13.3253 (4) Å
c = 9.1283 (3) Å
= 96.165 (2)°
V = 1319.87 (8) Å³
Z = 4
Mo K radiation
= 0.48 mm^-1
T = 298 K
0.20 × 0.20 × 0.18 mm

Data collection

Bruker SMART 1K diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001) T_min = 0.910, T_max = 0.918
7970 measured reflections
2863 independent reflections
2099 reflections with I > 2(I)
R_int = 0.023

Refinement

R[F² > 2(F²)] = 0.037
wR(F²) = 0.103
S = 1.05
2863 reflections
176 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
_max = 0.18 e Å^-3
_min = -0.23 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N2-H2O1ⁱ	0.889 (9)	2.065 (11)	2.9157 (18)	159.8 (18)
Symmetry code: (i) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: OM2272 ).

Acknowledgements

The Vital Foundation of Ankang University (project No. 2008AKXY012), and the Special Scientific Research Foundation of the Education Office of Shanxi Province (Project No. 02 J K202) are gratefully acknowledged.

References

Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Cao, G.-B. (2009a). Acta Cryst. E65, o2085.
Cao, G.-B. (2009b). Acta Cryst. E65, o2086.
Cao, G.-B. & Lu, X.-H. (2009a). Acta Cryst. E65, o1587.
Cao, G.-B. & Lu, X.-H. (2009b). Acta Cryst. E65, o1600.
Fun, H.-K., Patil, P. S., Rao, J. N., Kalluraya, B. & Chantrapromma, S. (2008). Acta Cryst. E64, o1707.
Li, C.-M. & Ban, H.-Y. (2009). Acta Cryst. E65, o1466.
Mohd Lair, N., Mohd Ali, H. & Ng, S. W. (2009). Acta Cryst. E65, o189.
Qu, L.-Z., Yang, T., Cao, G.-B. & Wang, X.-Y. (2008). Acta Cryst. E64, o2061.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Yang, D.-S. (2007). J. Chem. Crystallogr. 37, 343-348.
Yang, T., Cao, G.-B., Xiang, J.-M. & Zhang, L.-H. (2008). Acta Cryst. E64, o1186.
You, Z.-L., Dai, W.-M., Xu, X.-Q. & Hu, Y.-Q. (2008). Pol. J. Chem. 82, 2215-2219.
Zhu, C.-G., Wei, Y.-J. & Zhu, Q.-Y. (2009). Acta Cryst. E65, o85.

organic compounds