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Volume 69 
Part 8 
Page m428  
August 2013  

Received 27 May 2013
Accepted 4 June 2013
Online 3 July 2013

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.006 Å
R = 0.051
wR = 0.128
Data-to-parameter ratio = 18.7
Details
Open access

Bis(1-ethyl-4,4'-bipyridin-1-ium) bis(1,2-dicyanoethene-1,2-dithiolato-[kappa]2S,S')nickelate(II)

aDepartment of Applied Chemistry, College of Science, Nanjing University of Technology, Nanjing 210009, People's Republic of China
Correspondence e-mail: njutljl@163.com

In the anion of the title compound, (C12H13N2)[Ni(C4N2S2)2], the NiII atom is coordinated by four S atoms from two 1,2-dicyanoethene-1,2-dithiolate (mnt) ligands in a suqare-planar geometry. Weak C-H...N and C-H...S hydrogen bonds between the 1-ethyl-4,4'-bipyridin-1-ium cations and mnt anions and weak [pi]-[pi] interactions between the pyridine rings of the cations [centroid-centroid distances = 3.808 (3) and 3.972 (3) Å] lead to a two-dimensional network parallel to (010).

Related literature

For general background to bis(1,2-dithiolene) complexes acting as magnetic materials or showing non-linear optical properties, see: Duan et al. (2010[Duan, H.-B., Ren, X.-M. & Meng, Q.-J. (2010). Coord. Chem. Rev. 254, 1509-1522.]); Kato (2004[Kato, R. (2004). Chem. Rev. 104, 5319-5346.]). For the synthesis of the compound, see: Pei et al. (2010[Pei, W.-B., Wu, J.-S., Liu, J.-L., Ren, X.-M. & Shen, L.-J. (2010). Spectrochim. Acta Part A, 75, 191-197.]). For related structures, see: Duan et al. (2011[Duan, H.-B., Ren, X.-M., Shen, L.-J., Jin, W.-Q. & Zhou, S.-M. (2011). Dalton Trans. 40, 3622-3630.]); Liu et al. (2011[Liu, X., Liu, J.-L., Cai, B. & Ren, X.-M. (2011). Inorg. Chem. Commun. 14, 1428-1431.]).

[Scheme 1]

Experimental

Crystal data
  • (C12H13N2)[Ni(C4N2S2)2]

  • Mr = 709.58

  • Triclinic, [P \overline 1]

  • a = 7.4505 (13) Å

  • b = 12.793 (2) Å

  • c = 17.745 (3) Å

  • [alpha] = 78.664 (2)°

  • [beta] = 86.558 (2)°

  • [gamma] = 80.344 (2)°

  • V = 1634.2 (5) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.89 mm-1

  • T = 296 K

  • 0.25 × 0.20 × 0.15 mm

Data collection
  • Bruker APEX CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.808, Tmax = 0.876

  • 14954 measured reflections

  • 7631 independent reflections

  • 3616 reflections with I > 2[sigma](I)

  • Rint = 0.050

Refinement
  • R[F2 > 2[sigma](F2)] = 0.051

  • wR(F2) = 0.128

  • S = 0.97

  • 7631 reflections

  • 408 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.49 e Å-3

  • [Delta][rho]min = -0.37 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C13-H13...S2i 0.93 2.78 3.549 (4) 141
C17-H17...N4i 0.93 2.55 3.441 (6) 161
C21-H21...N3ii 0.93 2.42 3.342 (6) 170
C22-H22...N4ii 0.93 2.50 3.372 (5) 156
C24-H24...N2 0.93 2.46 3.364 (5) 163
C25-H25...N1 0.93 2.52 3.411 (6) 161
C27-H27...N4ii 0.93 2.58 3.498 (6) 172
C30-H30...N2 0.93 2.60 3.526 (6) 176
Symmetry codes: (i) -x+1, -y, -z+1; (ii) x-1, y, z+1.

Data collection: SMART (Bruker, 2007[Bruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). SMART and SAINT. 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: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HY2630 ).


Acknowledgements

The authors thank the Center of Testing and Analysis, Nanjing University of Technology, for support.

References

Bruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Duan, H.-B., Ren, X.-M. & Meng, Q.-J. (2010). Coord. Chem. Rev. 254, 1509-1522.  [Web of Science] [CrossRef] [ChemPort]
Duan, H.-B., Ren, X.-M., Shen, L.-J., Jin, W.-Q. & Zhou, S.-M. (2011). Dalton Trans. 40, 3622-3630.  [CSD] [CrossRef] [ChemPort] [PubMed]
Kato, R. (2004). Chem. Rev. 104, 5319-5346.  [Web of Science] [CrossRef] [PubMed] [ChemPort]
Liu, X., Liu, J.-L., Cai, B. & Ren, X.-M. (2011). Inorg. Chem. Commun. 14, 1428-1431.  [Web of Science] [CSD] [CrossRef] [ChemPort]
Pei, W.-B., Wu, J.-S., Liu, J.-L., Ren, X.-M. & Shen, L.-J. (2010). Spectrochim. Acta Part A, 75, 191-197.
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]


Acta Cryst (2013). E69, m428  [ doi:10.1107/S1600536813015493 ]

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