[Journal logo]

Volume 70 
Part 1 
Page o31  
January 2014  

Received 2 December 2013
Accepted 3 December 2013
Online 11 December 2013

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.004 Å
R = 0.053
wR = 0.145
Data-to-parameter ratio = 13.3
Details
Open access

N'-Benzyl­idene-2-chloro-N-(4-chloro­phen­yl)acetohydrazide

aDepartment of Studies in Physics, University of Mysore, Manasagangotri, Mysore 570 006, India, and bDepartment of Studies in Chemistry, Mangalore University, Mangalagangotri, Mangalore 574 199, India
Correspondence e-mail: dr@physics.uni-mysore.ac.in

In the title compound, C15H12Cl2N2O, the atoms not making up the chloro­benzene ring are approximately coplanar (r.m.s. deviation = 0.073 Å). The dihedral angle between these 13 atoms and the chloro­benzene ring is 67.37 (10)°. The C=O and Csp2-Cl groups are almost eclipsed [Cl-C-C=O = -6.5 (3)°]. In the crystal, C(6) chains linked by C-H...O hydrogen bonds result in [100] chains.

Related literature

For background to Schiff bases, see: Nithinchandra et al. (2013[Nithinchandra, Kalluraya, B., Shobhitha, S. & Babu, M. (2013). J. Chem. Pharm. Res. 5, 307-313.]); Shyma et al. (2013[Shyma, P. C., Kalluraya, B., Peethambar, S. K., Telkar, S. & Arulmoli, T. (2013). Eur. J. Med. Chem. 68, 394-404.]).

[Scheme 1]

Experimental

Crystal data
  • C15H12Cl2N2O

  • Mr = 307.17

  • Monoclinic, P 21 /c

  • a = 5.8548 (5) Å

  • b = 8.8892 (7) Å

  • c = 28.273 (2) Å

  • [beta] = 93.574 (4)°

  • V = 1468.6 (2) Å3

  • Z = 4

  • Cu K[alpha] radiation

  • [mu] = 3.95 mm-1

  • T = 296 K

  • 0.24 × 0.23 × 0.23 mm

Data collection
  • Bruker X8 Proteum diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2013[Bruker (2013). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.451, Tmax = 0.464

  • 10066 measured reflections

  • 2424 independent reflections

  • 2059 reflections with I > 2[sigma](I)

  • Rint = 0.061

Refinement
  • R[F2 > 2[sigma](F2)] = 0.053

  • wR(F2) = 0.145

  • S = 1.04

  • 2424 reflections

  • 182 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.46 e Å-3

  • [Delta][rho]min = -0.45 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C3-H3...O1i 0.93 2.40 3.256 (3) 154
Symmetry code: (i) x+1, y, z.

Data collection: APEX2 (Bruker, 2013[Bruker (2013). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2013[Bruker (2013). APEX2, 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: Mercury (Macrae et al., 2008[Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.]); software used to prepare material for publication: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB7168 ).


Acknowledgements

The authors are thankful to the IOE, University of Mysore, for providing the single-crystal X-ray diffraction facility. VN is grateful to the UGC for the award of an RFSMS Fellowship. RD acknowledges the UGC, New Delhi, for financial support under the Major Research Project Scheme [UGC MRP No. F.41-882/2012 (SR) dated 01/07/2012].

References

Bruker (2013). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Nithinchandra, Kalluraya, B., Shobhitha, S. & Babu, M. (2013). J. Chem. Pharm. Res. 5, 307-313.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Shyma, P. C., Kalluraya, B., Peethambar, S. K., Telkar, S. & Arulmoli, T. (2013). Eur. J. Med. Chem. 68, 394-404.  [Web of Science] [CrossRef] [ChemPort] [PubMed]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]


Acta Cryst (2014). E70, o31  [ doi:10.1107/S1600536813032790 ]

This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.