[Journal logo]

Volume 68 
Part 7 
Page m911  
July 2012  

Received 9 June 2012
Accepted 9 June 2012
Online 16 June 2012

Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.005 Å
R = 0.040
wR = 0.075
Data-to-parameter ratio = 16.8
Details
Open access

[2-(1-{2-[Azanidyl(ethylsulfanyl)methylidene-[kappa]N]hydrazin-1-ylidene-[kappa]N1}ethyl)phenolato-[kappa]O](pyridine-[kappa]N)nickel(II)

aDepartment of Chemistry, School of Sciences, Ferdowsi University of Mashhad, 91775-1436 Mashhad, Iran,bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia, and cChemistry Department and Faculty of Science, King Abdulaziz University, PO Box 80203 Jeddah, Saudi Arabia
Correspondence e-mail: edward.tiekink@gmail.com

The NiII atom in the title complex, [Ni(C11H13N3OS)(C5H5N)], exists within a square-planar N3O donor set provided by N,N',O atoms of the dianionic tridentate ligand and a pyridine N atom. The maximum deviation from the ideal geometry is seen in the N-Ni-N five-membered chelate bite angle of 83.28 (12)°. The pyridine molecule forms a dihedral angle of 44.43 (6)° with the N3O donor set. Supramolecular stacks along the a axis mediated by alternating [pi]-[pi] interactions between the pyridine and five- [centroid-centroid distance = 3.4784 (16) Å] and six-membered [3.4633 (17) Å] chelate rings, feature in the crystal packing.

Related literature

For the complexing ability of S-alkyl esters of thiosemicarbazone derivatives, see: Ahmadi et al. (2012[Ahmadi, M., Mague, T. J., Akbari, A. & Takjoo, R. (2012). Polyhedron, doi:10.1016/j.poly.2012.05.004.]). For medicinal applications of thiosemicarbazone, see: Dilworth & Hueting (2012[Dilworth, J. R. & Hueting, R. (2012). Inorg. Chim. Acta, 389, 3-15.]). For a related structure, see: Guveli & Ulkuseven (2011[Guveli, S. & Ulkuseven, B. (2011). Polyhedron, 30, 1385-1388.]).

[Scheme 1]

Experimental

Crystal data
  • [Ni(C11H13N3OS)(C5H5N)]

  • Mr = 373.11

  • Orthorhombic, P 21 21 21

  • a = 7.2956 (4) Å

  • b = 9.8463 (5) Å

  • c = 21.7489 (11) Å

  • V = 1562.33 (14) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 1.39 mm-1

  • T = 100 K

  • 0.35 × 0.10 × 0.05 mm

Data collection
  • Agilent SuperNova Dual diffractometer with an Atlas detector

  • Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012[Agilent (2012). CrysAlis PRO. Agilent Technologies, Yarnton, England.]) Tmin = 0.790, Tmax = 1.000

  • 6002 measured reflections

  • 3584 independent reflections

  • 3130 reflections with I > 2[sigma](I)

  • Rint = 0.037

Refinement
  • R[F2 > 2[sigma](F2)] = 0.040

  • wR(F2) = 0.075

  • S = 1.00

  • 3584 reflections

  • 213 parameters

  • 1 restraint

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

  • [Delta][rho]max = 0.45 e Å-3

  • [Delta][rho]min = -0.39 e Å-3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 1501 Friedel pairs

  • Flack parameter: -0.028 (16)

Table 1
Selected bond lengths (Å)

Ni-O1 1.828 (2)
Ni-N1 1.861 (2)
Ni-N3 1.845 (3)
Ni-N4 1.918 (2)

Data collection: CrysAlis PRO (Agilent, 2012[Agilent (2012). CrysAlis PRO. Agilent Technologies, 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 (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]) and DIAMOND (Brandenburg, 2006[Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); 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: HB6842 ).


Acknowledgements

The authors are grateful to the Ferdowsi University of Mashhad for financial support, and thank the Ministry of Higher Education (Malaysia) for funding structural studies through the High-Impact Research scheme (UM·C/HIR/MOHE/SC/3).

References

Agilent (2012). CrysAlis PRO. Agilent Technologies, Yarnton, England.
Ahmadi, M., Mague, T. J., Akbari, A. & Takjoo, R. (2012). Polyhedron, doi:10.1016/j.poly.2012.05.004.
Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Dilworth, J. R. & Hueting, R. (2012). Inorg. Chim. Acta, 389, 3-15.  [ISI] [CrossRef] [ChemPort]
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  [CrossRef] [details]
Flack, H. D. (1983). Acta Cryst. A39, 876-881.  [CrossRef] [details]
Guveli, S. & Ulkuseven, B. (2011). Polyhedron, 30, 1385-1388.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [ISI] [CrossRef] [ChemPort] [details]


Acta Cryst (2012). E68, m911  [ doi:10.1107/S1600536812026177 ]

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.