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Volume 69 
Part 11 
Pages m588-m589  
November 2013  

Received 27 September 2013
Accepted 30 September 2013
Online 9 October 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.004 Å
R = 0.034
wR = 0.092
Data-to-parameter ratio = 17.5
Details
Open access

Di­chlorido­{2-[(E)-phen­yl(pyridin-2-yl-[kappa]N)methyl­idene]-N-phenyl­hydra­zine­carboxamide-[kappa]2N2,O}copper(II)

aDepartment of Applied Chemistry, Cochin University of Science and Technology, Kochi 682 022, India,bDepartment of Chemistry, Faculty of Science, Eastern University, Sri Lanka, Chenkalady, Sri Lanka,cDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia, and dChemistry Department, King Abdulaziz University, PO Box 80203 Jeddah, Saudi Arabia
Correspondence e-mail: eesans@yahoo.com

The title compound, [CuCl2(C19H16N4O)], contains a CuII atom N,N',O-chelated by a neutral N-phenyl­hy­dra­zine­car­box­amide ligand and additionally coordinated by two Cl atoms, resulting in a distorted square-pyramidal geometry. The ligating atoms in the basal square plane of the complex comprise the azomethine N, the pyridine N, the amide O and one of the Cl atoms, whereas the other Cl atom occupies an apical position. The apical Cl atoms in adjacent layers function as hydrogen-bond acceptors to both NH groups. Intermolecular C-H...Cl and C-H...O interactions are also observed.

Related literature

For the biological applications of hydrazinecarboxamide and its derivatives, see: Beraldo & Gambino (2004[Beraldo, H. & Gambino, D. (2004). Mini Rev. Med. Chem. 4, 31-39.]); Kasuga et al. (2006[Kasuga, N. C., Onodera, K., Nakano, S., Hayashi, K. & Nomiya, K. (2006). J. Inorg. Biochem. 100, 1176-1186.]); Rivadeneira et al. (2009[Rivadeneira, J., Barrio, D. A., Arrambide, G., Gambino, D., Bruzzone, L. & Etcheverry, S. B. (2009). J. Inorg. Biochem. 103, 633-642.]); Shalini et al. (2009[Shalini, M., Yogeeswari, P., Sriram, D. & Stables, J. P. (2009). Biomed. Pharmacother. 63, 187-193.]); Rodriguez-Arguelles et al. (2010[Rodriguez-Arguelles, M. C., Mosquera-Vazquez, S., Sanmartin-Matalobos, J., Garcia-Deibe, A. M., Pelizzi, C. & Zani, F. (2010). Polyhedron, 29, 864-870.]). For the synthesis of related compounds, see: Kurup et al. (2011[Kurup, M. R. P., Varghese, B., Sithambaresan, M., Krishnan, S., Sheeja, S. R. & Suresh, E. (2011). Polyhedron, 30, 70-78.]). For related structures, see: Kunnath et al. (2012[Kunnath, R. J., Prathapachandra Kurup, M. R. & Ng, S. W. (2012). Acta Cryst. E68, m1181.]). For the calculation of the trigonality index, see: Addison et al. (1984[Addison, A. W., Rao, J. N., Reedijk, J. & Vershoor, G. C. (1984). Dalton Trans. pp. 1349-1356.]). For the graph-set notation, see: Etter et al. (1990[Etter, M. C., MacDonald, J. C. & Bernstein, J. (1990). Acta Cryst. B46, 256-262.]).

[Scheme 1]

Experimental

Crystal data
  • [CuCl2(C19H16N4O)]

  • Mr = 450.81

  • Triclinic, [P \overline 1]

  • a = 9.4483 (5) Å

  • b = 9.8197 (3) Å

  • c = 11.5307 (4) Å

  • [alpha] = 104.067 (1)°

  • [beta] = 103.026 (1)°

  • [gamma] = 100.475 (1)°

  • V = 978.83 (7) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 1.41 mm-1

  • T = 293 K

  • 0.35 × 0.32 × 0.30 mm

Data collection
  • Bruker Kappa APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2004[Bruker (2004). SADABS, APEX2, XPREP and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.614, Tmax = 0.649

  • 7149 measured reflections

  • 4411 independent reflections

  • 3550 reflections with I > 2[sigma](I)

  • Rint = 0.020

Refinement
  • R[F2 > 2[sigma](F2)] = 0.034

  • wR(F2) = 0.092

  • S = 1.01

  • 4411 reflections

  • 252 parameters

  • 2 restraints

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

  • [Delta][rho]max = 0.34 e Å-3

  • [Delta][rho]min = -0.40 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N3-H3'...Cl1i 0.85 (2) 2.40 (2) 3.1397 (18) 147 (2)
N4-H4'...Cl1i 0.83 (2) 2.35 (2) 3.136 (2) 159 (2)
C2-H2...Cl1ii 0.93 2.69 3.589 (4) 163
C19-H19...O1 0.93 2.36 2.953 (4) 121
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) -x+2, -y+2, -z+1.

Data collection: APEX2 (Bruker, 2004[Bruker (2004). SADABS, APEX2, XPREP and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: APEX2/SAINT (Bruker, 2004[Bruker (2004). SADABS, APEX2, XPREP and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT/XPREP (Bruker, 2004[Bruker (2004). SADABS, APEX2, XPREP and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); program(s) used to solve structure: SHELXL97 (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 (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and DIAMOND (Brandenburg, 2010[Brandenburg, K. (2010). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: SHELXL97 and publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: FJ2644 ).


Acknowledgements

NA thanks the University Grants Commission (India) for a Junior Research Fellowship. We thank the Sophisticated Analytical Instruments Facility, Cochin University of S&T, for the diffraction measurements. MRPK thanks the University Grants Commission, New Delhi, for a UGC-BSR one-time grant to faculty. We also thank the Ministry of Higher Education of Malaysia (grant No. UM·C/HIR/MOHE/SC/12) for supporting this study.

References

Addison, A. W., Rao, J. N., Reedijk, J. & Vershoor, G. C. (1984). Dalton Trans. pp. 1349-1356.
Beraldo, H. & Gambino, D. (2004). Mini Rev. Med. Chem. 4, 31-39.  [CrossRef] [PubMed] [ChemPort]
Brandenburg, K. (2010). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Bruker (2004). SADABS, APEX2, XPREP and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Etter, M. C., MacDonald, J. C. & Bernstein, J. (1990). Acta Cryst. B46, 256-262.  [CrossRef] [Web of Science] [IUCr Journals]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Kasuga, N. C., Onodera, K., Nakano, S., Hayashi, K. & Nomiya, K. (2006). J. Inorg. Biochem. 100, 1176-1186.  [Web of Science] [CSD] [CrossRef] [PubMed] [ChemPort]
Kunnath, R. J., Prathapachandra Kurup, M. R. & Ng, S. W. (2012). Acta Cryst. E68, m1181.  [CSD] [CrossRef] [IUCr Journals]
Kurup, M. R. P., Varghese, B., Sithambaresan, M., Krishnan, S., Sheeja, S. R. & Suresh, E. (2011). Polyhedron, 30, 70-78.  [Web of Science] [CSD] [CrossRef] [ChemPort]
Rivadeneira, J., Barrio, D. A., Arrambide, G., Gambino, D., Bruzzone, L. & Etcheverry, S. B. (2009). J. Inorg. Biochem. 103, 633-642.  [Web of Science] [CrossRef] [PubMed] [ChemPort]
Rodriguez-Arguelles, M. C., Mosquera-Vazquez, S., Sanmartin-Matalobos, J., Garcia-Deibe, A. M., Pelizzi, C. & Zani, F. (2010). Polyhedron, 29, 864-870.
Shalini, M., Yogeeswari, P., Sriram, D. & Stables, J. P. (2009). Biomed. Pharmacother. 63, 187-193.  [CrossRef] [PubMed] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]


Acta Cryst (2013). E69, m588-m589   [ doi:10.1107/S1600536813026883 ]

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