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Volume 69 
Part 6 
Page m312  
June 2013  

Received 27 April 2013
Accepted 7 May 2013
Online 11 May 2013

Key indicators
Single-crystal X-ray study
T = 291 K
Mean [sigma](C-C) = 0.005 Å
R = 0.036
wR = 0.083
Data-to-parameter ratio = 14.0
Details
Open access

1,1'-(Ethane-1,2-diyl)dipyridinium bis(1,2-dicyanoethene-1,2-dithiolato-[kappa]2S,S')cuprate(II)

aSchool of Biology and Chemistry Engineering, Jiangsu University of Science and Technology, Zhenjiang, Jiangsu 212003, People's Republic of China, and bNational Food Packaging Products Quality Supervision and Inspection Center, Jiangsu Provincial Supervising and Testing Research Institute for Products Quality, Nanjing 210007, People's Republic of China
Correspondence e-mail: wangfmzj@hotmail.com

In the title ion-pair complex, (C12H14N2)[Cu(C4N2S2)2], the complex anion exhibits a highly twisted coordination environment around the tetracoordinated CuII atom. The dihedral angles between the 1,2-dicyanoethene-1,2-dithiolato ligands and between the two pyridine rings in the cation are 37.49 (3) and 29.18 (10)°, respectively. Weak C-H...N and C-H...S hydrogen bonds link the cations and anions into a three-dimensional network.

Related literature

For background to crystalline molecular materials and coordination polymer networks, see: Brammer (2004[Brammer, L. (2004). Chem. Soc. Rev. 33, 476-489.]); Robin & Fromm (2006[Robin, A. Y. & Fromm, K. M. (2006). Coord. Chem. Rev. 250, 2127-2157.]). For 1,2-dithiolene-metal complexes, see: Duan et al. (2010[Duan, H.-B., Ren, X.-M. & Meng, Q.-J. (2010). Coord. Chem. Rev. 254, 1509-1522.]); Ni et al. (2005[Ni, Z.-P., Ren, X.-M., Ma, J., Xie, J.-L., Ni, C.-L., Chen, Z.-D. & Meng, Q.-J. (2005). J. Am. Chem. Soc. 127, 14330-14338.]). For related structures, see: Ren et al. (2006[Ren, X.-M., Ni, Z.-P., Noro, S., Akutagawa, T., Nishihara, S., Nakamura, T., Sui, Y.-X. & Song, Y. (2006). Cryst. Growth Des. 6, 2530-2537.]); Wang et al. (2012[Wang, F.-M., Chen, L.-Z., Liu, Y.-M., Lu, C.-S., Duan, X.-Y. & Meng, Q.-J. (2012). J. Coord. Chem. 65, 87-103.]).

[Scheme 1]

Experimental

Crystal data
  • (C12H14N2)[Cu(C4N2S2)2]

  • Mr = 530.20

  • Triclinic, [P \overline 1]

  • a = 7.7598 (10) Å

  • b = 12.3811 (15) Å

  • c = 12.6572 (16) Å

  • [alpha] = 77.676 (2)°

  • [beta] = 72.791 (2)°

  • [gamma] = 84.122 (2)°

  • V = 1133.8 (2) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 1.35 mm-1

  • T = 291 K

  • 0.25 × 0.20 × 0.15 mm

Data collection
  • Bruker APEX CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2001[Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.730, Tmax = 0.815

  • 5682 measured reflections

  • 3921 independent reflections

  • 3217 reflections with I > 2[sigma](I)

  • Rint = 0.054

Refinement
  • R[F2 > 2[sigma](F2)] = 0.036

  • wR(F2) = 0.083

  • S = 1.00

  • 3921 reflections

  • 280 parameters

  • 1 restraint

  • H-atom parameters constrained

  • [Delta][rho]max = 0.39 e Å-3

  • [Delta][rho]min = -0.26 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C11-H11A...N2i 0.93 2.61 3.356 (4) 137
C14-H14A...N4ii 0.97 2.60 3.341 (4) 133
C14-H14B...N1iii 0.97 2.60 3.479 (4) 151
C15-H15B...S1 0.97 2.83 3.769 (3) 163
C16-H16A...N2iv 0.93 2.56 3.368 (4) 146
C17-H17A...S2iv 0.93 2.82 3.743 (3) 171
C19-H19A...N3v 0.93 2.56 3.235 (4) 129
C20-H20A...N1iii 0.93 2.52 3.422 (4) 164
Symmetry codes: (i) x, y-1, z; (ii) -x+1, -y, -z+1; (iii) -x+1, -y+1, -z; (iv) -x+1, -y+1, -z+1; (v) x-1, y+1, z.

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: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HY2624 ).


Acknowledgements

This work was supported by the National Natural Science Foundation of China for Young Scholars (grant No. 21201087), the Natural Science Foundation of Jiangsu Provincial Department of Education (grant No. 11KJB150004), the Science and Technology Project of the State General Administration of Quality Supervision, Inspection and Quarantine, People's Republic of China (grant Nos. 2011QK121 and 2011QK122) and a start-up grant from Jiangsu University of Science and Technology.

References

Brammer, L. (2004). Chem. Soc. Rev. 33, 476-489.  [ISI] [CrossRef] [PubMed] [ChemPort]
Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
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.  [ISI] [CrossRef] [ChemPort]
Ni, Z.-P., Ren, X.-M., Ma, J., Xie, J.-L., Ni, C.-L., Chen, Z.-D. & Meng, Q.-J. (2005). J. Am. Chem. Soc. 127, 14330-14338.  [ISI] [CrossRef] [PubMed] [ChemPort]
Ren, X.-M., Ni, Z.-P., Noro, S., Akutagawa, T., Nishihara, S., Nakamura, T., Sui, Y.-X. & Song, Y. (2006). Cryst. Growth Des. 6, 2530-2537.  [CSD] [CrossRef] [ChemPort]
Robin, A. Y. & Fromm, K. M. (2006). Coord. Chem. Rev. 250, 2127-2157.  [ISI] [CrossRef] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Wang, F.-M., Chen, L.-Z., Liu, Y.-M., Lu, C.-S., Duan, X.-Y. & Meng, Q.-J. (2012). J. Coord. Chem. 65, 87-103.  [ISI] [CSD] [CrossRef] [ChemPort]


Acta Cryst (2013). E69, m312  [ doi:10.1107/S1600536813012439 ]

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