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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 [sigma](C-C) = 0.003 Å
R = 0.048
wR = 0.130
Data-to-parameter ratio = 16.9
Details
Open access

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

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-H...O and C-H...O hydrogen bonds, forming chains along the c axis.

Related literature

For background to hydrazones, see: El-Asmy et al. (2010[El-Asmy, A. A., El-Gammal, O. A., Radwan, H. A. & Ghazy, S. E. (2010). Spectrochim. Acta Part A, 77, 297-303.]); El-Sherif (2009[El-Sherif, A. A. (2009). Inorg. Chim. Acta, 362, 4991-5000.]); Singh et al. (2009[Singh, V., Katiyar, A. & Singh, S. (2009). J. Coord. Chem. 62, 1336-1346.]); El-Tabl et al. (2007[El-Tabl, A. S., El-Saied, F. A. & Al-Hakimi, A. N. (2007). Transition Met. Chem. 32, 689-701.]); Lei (2011[Lei, Y. (2011). Acta Cryst. E67, o162.]). For structures of hydrazone compounds, see: Qiao et al. (2010[Qiao, Y., Ju, X., Gao, Z. & Kong, L. (2010). Acta Cryst. E66, o95.]); Hussain et al. (2010[Hussain, A., Shafiq, Z., Tahir, M. N. & Yaqub, M. (2010). Acta Cryst. E66, o1888.]); Han & Zhao (2010[Han, Y.-Y. & Zhao, Q.-R. (2010). Acta Cryst. E66, o1041.]); Ahmad et al. (2010[Ahmad, T., Zia-ur-Rehman, M., Siddiqui, H. L., Mahmud, S. & Parvez, M. (2010). Acta Cryst. E66, o1022.]).

[Scheme 1]

Experimental

Crystal data
  • C14H10Cl2N2O

  • Mr = 293.14

  • Monoclinic, P 21 /c

  • a = 13.106 (3) Å

  • b = 12.588 (3) Å

  • c = 8.347 (2) Å

  • [beta] = 97.578 (2)°

  • V = 1365.0 (6) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 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[Bruker (2000). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.865, Tmax = 0.873

  • 6893 measured reflections

  • 2954 independent reflections

  • 1936 reflections with I > 2[sigma](I)

  • Rint = 0.032

Refinement
  • R[F2 > 2[sigma](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

  • [Delta][rho]max = 0.26 e Å-3

  • [Delta][rho]min = -0.48 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N2-H2...O1i 0.90 (1) 1.98 (1) 2.854 (2) 164 (2)
C7-H7...O1i 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[Bruker (2000). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2000[Bruker (2000). SMART, SAINT and SADABS. 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: 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.  [CSD] [CrossRef] [details]
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.  [ISI] [CrossRef] [ChemPort]
El-Tabl, A. S., El-Saied, F. A. & Al-Hakimi, A. N. (2007). Transition Met. Chem. 32, 689-701.  [ChemPort]
Han, Y.-Y. & Zhao, Q.-R. (2010). Acta Cryst. E66, o1041.  [CSD] [CrossRef] [details]
Hussain, A., Shafiq, Z., Tahir, M. N. & Yaqub, M. (2010). Acta Cryst. E66, o1888.  [CSD] [CrossRef] [details]
Lei, Y. (2011). Acta Cryst. E67, o162.  [CrossRef] [details]
Qiao, Y., Ju, X., Gao, Z. & Kong, L. (2010). Acta Cryst. E66, o95.  [CSD] [CrossRef] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Singh, V., Katiyar, A. & Singh, S. (2009). J. Coord. Chem. 62, 1336-1346.  [CrossRef] [ChemPort]


Acta Cryst (2011). E67, o410  [ doi:10.1107/S1600536811001656 ]

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