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Volume 69 
Part 6 
Pages m323-m324  
June 2013  

Received 30 April 2013
Accepted 13 May 2013
Online 18 May 2013

Key indicators
Single-crystal X-ray study
T = 150 K
Mean [sigma](C-C) = 0.016 Å
R = 0.045
wR = 0.121
Data-to-parameter ratio = 11.7
Details
Open access

Bis{(Z)-[(E)-2-(pyridin-2-ylmethylidene)hydrazin-1-ylidene][(pyridin-2-yl)methylsulfanyl]methanethiolato}nickel(II)

aSchool of Pharmacy, University of Nottingham Malaysia Campus, Selangor, Malaysia,bSchool of Chemical Sciences and Food Technology, Universiti Kebangsaan Malaysia, 43600 Bangi, Malaysia,cDepartment of Chemistry, Faculty of Science, Universiti Putra Malaysia, Malaysia, and dChemical Crystallography, Chemistry Research Laboratory, 12 Mansfield Road, Oxford OX1 3TA, England
Correspondence e-mail: tengjin.khoo@nottingham.edu.my

The title compound, [Ni(C13H11N4S2)2], was obtained by the reaction of S-2-picolyldithiocarbazate and pyridine-2-carbaldehyde with nickel(II) acetate. The NiII atom is located on a twofold rotation axis and is bonded to four N atoms at distances of 2.037 (8) and 2.109 (9) Å, and to two S atoms at a distance of 2.406 (3) Å, leading to a distorted octahedral coordination. The angle between the mean planes of the coordinating moieties of the two symmetry-related tridentate ligands is 83.3 (2)°. In the crystal, complex molecules are linked by weak C-H...S hydrogen bonds, [pi]-[pi] interactions between the pyridine rings [centroid-centroid distance = 3.775 (9) Å] and C-H...[pi] interactions. The hydrogen-bonding interactions lead to the formation of layers parallel to (010); [pi]-[pi] interactions link these layers into a three-dimensional network.

Related literature

For biological applications of Schiff base ligands and complexes derived from dithiocarbazates, see: Hossain et al. (1996[Hossain, E., Alam, M., Ali, M., Nazimuddin, M., Smith, E. & Hynes, C. (1996). Polyhedron, 15, 973-980.]); Tarafder et al. (2002[Tarafder, M., Khoo, T. J., Crouse, K. A., Ali, M., Yamin, B. & Fun, H.-K. (2002). Polyhedron, 21, 2691-2698.]); Crouse et al. (2004[Crouse, K. A., Chew, -B., Tarafder, M., Kasbollah, A., Ali, M., Yamin, M. & Fun, H. K. (2004). Polyhedron, 23, 161-168.]). For a related structure, see: Omar et al. (2012[Omar, S. A., Ravoof, T. B. S. A., Mohamed Tahir, M. I. & Crouse, K. A. (2012). Acta Cryst. E68, m316-m317.]).

[Scheme 1]

Experimental

Crystal data
  • [Ni(C13H11N4S2)2]

  • Mr = 633.49

  • Monoclinic, C 2/c

  • a = 26.0501 (4) Å

  • b = 8.0057 (1) Å

  • c = 13.0743 (2) Å

  • [beta] = 103.8993 (9)°

  • V = 2646.80 (7) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 1.08 mm-1

  • T = 150 K

  • 0.04 × 0.03 × 0.02 mm

Data collection
  • Nonius Kappa CCD diffractometer

  • Absorption correction: multi-scan (DENZO/SCALEPACK; Otwinowski & Minor, 1997[Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.]) Tmin = 0.97, Tmax = 0.98

  • 5912 measured reflections

  • 3030 independent reflections

  • 2066 reflections with I > 3[sigma](I)

  • Rint = 0.020

Refinement
  • R[F2 > 2[sigma](F2)] = 0.045

  • wR(F2) = 0.121

  • S = 1.08

  • 2066 reflections

  • 177 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.81 e Å-3

  • [Delta][rho]min = -0.74 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the pyridine ring (C9-C13/N4).

D-H...A D-H H...A D...A D-H...A
C8-H7...S2i 0.94 2.72 3.644 (9) 166
C4-H4...S2i 0.95 2.92 3.862 (11) 175
C6-H6...Cgii 0.98 2.98 3.750 (12) 136
Symmetry codes: (i) [x, -y, z+{\script{1\over 2}}]; (ii) -x+1, -y, -z+2.

Data collection: COLLECT (Nonius, 2001[Nonius (2001). COLLECT. Nonius BV, Delft, The Netherlands.]); cell refinement: DENZO/SCALEPACK (Otwinowski & Minor, 1997[Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.]); data reduction: DENZO/SCALEPACK; program(s) used to solve structure: SIR92 (Altomare et al., 1994[Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M. C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435.]); program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003[Betteridge, P. W., Carruthers, J. R., Cooper, R. I., Prout, K. & Watkin, D. J. (2003). J. Appl. Cryst. 36, 1487.]); molecular graphics: Mercury (Macrae et al., 2006[Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.]); software used to prepare material for publication: 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: WM2742 ).


Acknowledgements

The authors thank the Ministry of Higher Education Malaysia (MOHE) under FRGS (F0010.54.02) for providing a grant for this study.

References

Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M. C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435.  [CrossRef] [details]
Betteridge, P. W., Carruthers, J. R., Cooper, R. I., Prout, K. & Watkin, D. J. (2003). J. Appl. Cryst. 36, 1487.  [ISI] [CrossRef] [details]
Crouse, K. A., Chew, -B., Tarafder, M., Kasbollah, A., Ali, M., Yamin, M. & Fun, H. K. (2004). Polyhedron, 23, 161-168.  [ISI] [CSD] [CrossRef] [ChemPort]
Hossain, E., Alam, M., Ali, M., Nazimuddin, M., Smith, E. & Hynes, C. (1996). Polyhedron, 15, 973-980.  [CrossRef] [ChemPort] [ISI]
Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.  [ISI] [CrossRef] [ChemPort] [details]
Nonius (2001). COLLECT. Nonius BV, Delft, The Netherlands.
Omar, S. A., Ravoof, T. B. S. A., Mohamed Tahir, M. I. & Crouse, K. A. (2012). Acta Cryst. E68, m316-m317.  [CSD] [CrossRef] [ChemPort] [details]
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.
Tarafder, M., Khoo, T. J., Crouse, K. A., Ali, M., Yamin, B. & Fun, H.-K. (2002). Polyhedron, 21, 2691-2698.  [ISI] [CSD] [CrossRef] [ChemPort]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [ISI] [CrossRef] [ChemPort] [details]


Acta Cryst (2013). E69, m323-m324   [ doi:10.1107/S1600536813013032 ]

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