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Volume 70 
Part 1 
Page o13  
January 2014  

Received 28 October 2013
Accepted 27 November 2013
Online 4 December 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.004 Å
R = 0.048
wR = 0.118
Data-to-parameter ratio = 15.1
Details
Open access

Dimethyl 2-[2-(2,4,6-tri­chloro­phen­yl)hydrazin-1-yl­idene]butane­dioate

aDepartment of Studies in Physics, University of Mysore, Manasagangotri, Mysore 570 006, India,bDepartment of Studies in Chemistry, Mangalore University, Mangalagangotri, Mangalore 574 199, India, and cPost-Graduate Department of Physics & Electronics, University of Jammu, Jammu Tawi 180 006, India
Correspondence e-mail: dr@physics.uni-mysore.ac.in

In the title compound, C12H11Cl3N2O4, the dihedral angle between the aromatic ring and the hydrazine (NH-N=C) grouping is 52.2 (3)°. The butanedioate groups exhibit planar conformations. An intra­molecular N-H...O hydrogen bond links the N-H group of the hydrazine to one of the meth­oxy groups of the butane­dioate moiety. In the crystal, mol­ecules are linked by C-H...O hydrogen bonds and [pi]-[pi] inter­actions are also observed [centroid-centroid separation = 3.535 (1) Å].

Related literature

For the pharmacological activity of halo-substituted derivatives, see: Kees et al. (1996[Kees, K. L., Fitzgerald, J. J. Jr, Steiner, K. E., Mattes, J. F., Mihan, B., Tosi, T., Mondoro, D. & McCalebr, M. L. (1996). J. Med. Chem. 39, 3920-3928.]). For the use of the title compound in the synthesis of pyrazoles, see: Palacios et al. (1999[Palacios, F., de Retana, A. M. O. & Pagalday, J. (1999). Tetrahedron, 55, 14451-14458.]). For the biological activity of pyrazoles, see: Palacios et al. (1999[Palacios, F., de Retana, A. M. O. & Pagalday, J. (1999). Tetrahedron, 55, 14451-14458.]); Lee et al. (2003[Lee, K. Y., Kim, J. M. & Kim, J. N. (2003). Tetrahedron Lett. 44, 6737-6740.]); Nithinchandra et al. (2012[Nithinchandra, Kalluraya, B., Aamir, S. & Shabaraya, A. R. (2012). Eur. J. Med. Chem. 54, 597-604.]); Genin et al. (2000[Genin, W. G., Yagi, Y. & Romero, D. L. (2000). J. Med. Chem. 43, 1034-1040.]); Reddy et al. (2008[Reddy, M. V. R., Billa, V. K., Pallela, V. R., Mallireddigari, M. R., Boominathan, R., Gabriel, J. L. & Reddy, E. P. (2008). Bioorg. Med. Chem. 16, 3907-3916.]); Kees et al. (1996[Kees, K. L., Fitzgerald, J. J. Jr, Steiner, K. E., Mattes, J. F., Mihan, B., Tosi, T., Mondoro, D. & McCalebr, M. L. (1996). J. Med. Chem. 39, 3920-3928.]). For a related structure, see: Huang et al. (2011[Huang, Y.-L., Li, D.-F., Sun, J., Gao, J.-H. & Shan, S. (2011). Acta Cryst. E67, o528.]).

[Scheme 1]

Experimental

Crystal data
  • C12H11Cl3N2O4

  • Mr = 353.58

  • Orthorhombic, P b c a

  • a = 7.0182 (5) Å

  • b = 16.0165 (12) Å

  • c = 26.7488 (15) Å

  • V = 3006.8 (4) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 0.63 mm-1

  • T = 293 K

  • 0.30 × 0.20 × 0.20 mm

Data collection
  • Oxford Diffraction Xcalibur Sapphire3 diffractometer

  • Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2010[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]) Tmin = 0.716, Tmax = 1.000

  • 7083 measured reflections

  • 2954 independent reflections

  • 1844 reflections with I > 2[sigma](I)

  • Rint = 0.040

Refinement
  • R[F2 > 2[sigma](F2)] = 0.048

  • wR(F2) = 0.118

  • S = 1.03

  • 2954 reflections

  • 195 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • [Delta][rho]max = 0.26 e Å-3

  • [Delta][rho]min = -0.24 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N10-H10...O15 0.87 (3) 2.38 (3) 3.047 (3) 133 (3)
C5-H5...O19i 0.93 2.51 3.397 (4) 159
Symmetry code: (i) [x-{\script{1\over 2}}, y, -z+{\script{1\over 2}}].

Data collection: CrysAlis PRO (Oxford Diffraction, 2010[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); 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: SJ5364 ).


Acknowledgements

MKU thanks the Department of Science & Technology (DST), New Delhi, for the award of an INSPIRE Fellowship. DR acknowledges the UGC for financial support under the Major Research Project scheme [No. F.41-882/2012 (SR)]. RK acknowledges the DST, New Delhi, for the single-crystal X-ray diffractometer sanctioned as a National Facility.

References

Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Genin, W. G., Yagi, Y. & Romero, D. L. (2000). J. Med. Chem. 43, 1034-1040.  [Web of Science] [CrossRef] [PubMed] [ChemPort]
Huang, Y.-L., Li, D.-F., Sun, J., Gao, J.-H. & Shan, S. (2011). Acta Cryst. E67, o528.  [CSD] [CrossRef] [IUCr Journals]
Kees, K. L., Fitzgerald, J. J. Jr, Steiner, K. E., Mattes, J. F., Mihan, B., Tosi, T., Mondoro, D. & McCalebr, M. L. (1996). J. Med. Chem. 39, 3920-3928.  [CrossRef] [ChemPort] [PubMed] [Web of Science]
Lee, K. Y., Kim, J. M. & Kim, J. N. (2003). Tetrahedron Lett. 44, 6737-6740.  [Web of Science] [CrossRef] [ChemPort]
Nithinchandra, Kalluraya, B., Aamir, S. & Shabaraya, A. R. (2012). Eur. J. Med. Chem. 54, 597-604.  [Web of Science] [CrossRef] [ChemPort] [PubMed]
Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.
Palacios, F., de Retana, A. M. O. & Pagalday, J. (1999). Tetrahedron, 55, 14451-14458.  [Web of Science] [CrossRef] [ChemPort]
Reddy, M. V. R., Billa, V. K., Pallela, V. R., Mallireddigari, M. R., Boominathan, R., Gabriel, J. L. & Reddy, E. P. (2008). Bioorg. Med. Chem. 16, 3907-3916.  [CrossRef] [PubMed] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]


Acta Cryst (2014). E70, o13  [ doi:10.1107/S160053681303242X ]

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