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Volume 69 
Part 10 
Pages m556-m557  
October 2013  

Received 29 July 2013
Accepted 11 September 2013
Online 21 September 2013

Key indicators
Single-crystal X-ray study
T = 291 K
Mean [sigma](C-C) = 0.006 Å
R = 0.027
wR = 0.071
Data-to-parameter ratio = 16.2
Details
Open access

Bis((E)-2-{5,5-dimethyl-3-[4-(1H-1,2,4-triazol-1-yl-[kappa]N4)styryl]cyclohex-2-enylidene}malononitrile)diiodidomercury(II)

aDeparment of Chemistry, Anhui University, Hefei 230039, People's Republic of China and Key Laboratory of Functional Inorganic Materials Chemistry, Hefei 230039, People's Republic of China
Correspondence e-mail: zhpzhp@263.net

In the title complex, [HgI2(C21H19N5)2], the HgII ion is located on a twofold rotation axis and is coordinated by two I atoms and two N atoms from two (E)-2-{5,5-dimethyl-3-[4-(1H-1,2,4-triazol-1-yl)styryl]cyclohex-2-enylidene}malononitrile ligands in a distorted tetrahedral geometry. In the crystal, the molecules are linked by intermolecular [pi]-[pi] interactions between the triazole and benzene rings [centroid-centroid distance = 3.794 (3) Å] into a band extending in [010]. These bands are further connected by C-H...N hydrogen bonds into a two-dimensional network parallel to (100).

Related literature

For background to metal-organic complexes, see: Haneda et al. (2007[Haneda, S., Gan, Z. B., Eda, K. & Hayashi, M. (2007). Organometallics, 26, 6551-6555.]); Li et al. (2006[Li, Y.-Y., Lin, C.-K., Zheng, G.-L., Cheng, Z.-Y., You, H., Wang, W.-D. & Lin, J. (2006). Chem. Mater. 18, 3463-3469.]); Liu et al. (2010[Liu, Q.-K., Ma, J.-P. & Dong, Y.-B. (2010). J. Am. Chem. Soc. 132, 7005-7017.], 2011[Liu, Q.-K., Ma, J.-P. & Dong, Y.-B. (2011). Chem. Commun. 47, 12343-12345.]); Satapathy et al. (2012[Satapathy, R., Wu, Y. H. & Lin, H. C. (2012). Org. Lett. 14, 2564-2567.]); Sun et al. (2012[Sun, L., Li, G.-Z., Xu, M.-H., Li, X.-J., Li, J. R. & Deng, H. (2012). Eur. J. Inorg. Chem. pp. 1764-1772.]). For the organic ligand of the title compound, see: Zheng et al. (2013[Zheng, Z., Yu, Z.-P., Yang, M.-D., Jin, F., Zhang, Q., Zhou, H.-P., Wu, J.-Y. & Tian, Y.-P. (2013). J. Org. Chem. 78, 3222-3234.]). For related structures, see: Jin, Wang et al. (2013[Jin, F., Wang, H.-Z., Zhang, Y., Wang, Y., Zhang, J., Kong, L., Hao, F.-Y., Yang, J.-X., Wu, J.-Y., Tian, Y.-P. & Zhou, H.-P. (2013). CrystEngComm, 15, 3687-3695.]); Jin, Zhang et al. (2013[Jin, F., Zhang, Y., Wang, H.-Z., Zhu, H.-Z., Yan, Y., Zhang, J., Wu, J.-Y., Tian, Y.-P. & Zhou, H.-P. (2013). Cryst. Growth Des. 13, 1978-1987.]); Zhou et al. (2009[Zhou, H.-P., Yin, J.-H., Zheng, L.-X., Wang, P., Hao, F.-Y., Geng, W.-Q., Gan, X.-P., Xu, G.-Y., Wu, J.-Y., Tian, Y.-P., Tao, X.-T., Jiang, M.-H. & Kan, Y.-H. (2009). Cryst. Growth Des. 9, 3789-3798.]).

[Scheme 1]

Experimental

Crystal data
  • [HgI2(C21H19N5)2]

  • Mr = 1137.21

  • Monoclinic, C 2/c

  • a = 38.9622 (16) Å

  • b = 5.5684 (12) Å

  • c = 21.9564 (14) Å

  • [beta] = 117.738 (2)°

  • V = 4216.2 (10) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 5.16 mm-1

  • T = 291 K

  • 0.30 × 0.20 × 0.18 mm

Data collection
  • Bruker APEX CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2001[Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.307, Tmax = 0.457

  • 14961 measured reflections

  • 4078 independent reflections

  • 3384 reflections with I > 2[sigma](I)

  • Rint = 0.032

Refinement
  • R[F2 > 2[sigma](F2)] = 0.027

  • wR(F2) = 0.071

  • S = 1.01

  • 4078 reflections

  • 251 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.78 e Å-3

  • [Delta][rho]min = -0.52 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C20-H20...N2i 0.93 2.48 3.354 (7) 157
Symmetry code: (i) [x, -y+1, z+{\script{1\over 2}}].

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: XP in SHELXTL and DIAMOND (Brandenburg, 1999[Brandenburg, K. (1999). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: SHELXTL.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HY2634 ).


Acknowledgements

This work was supported by the Program for New Century Excellent Talents in Universities (China), the Doctoral Program Foundation of the Ministry of Education of China (grant No. 20113401110004), the National Natural Science Foundation of China (grant Nos. 21271003 and 21271004), the Natural Science Foundation of the Education Committee of Anhui Province (grant No. KJ2012A024), the Natural Science Foundation of Anhui Province (grant No. 1208085MB22) and the 211 Project of Anhui University.

References

Brandenburg, K. (1999). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Haneda, S., Gan, Z. B., Eda, K. & Hayashi, M. (2007). Organometallics, 26, 6551-6555.  [CSD] [CrossRef] [ChemPort]
Jin, F., Wang, H.-Z., Zhang, Y., Wang, Y., Zhang, J., Kong, L., Hao, F.-Y., Yang, J.-X., Wu, J.-Y., Tian, Y.-P. & Zhou, H.-P. (2013). CrystEngComm, 15, 3687-3695.  [Web of Science] [CSD] [CrossRef] [ChemPort]
Jin, F., Zhang, Y., Wang, H.-Z., Zhu, H.-Z., Yan, Y., Zhang, J., Wu, J.-Y., Tian, Y.-P. & Zhou, H.-P. (2013). Cryst. Growth Des. 13, 1978-1987.  [CSD] [CrossRef] [ChemPort]
Li, Y.-Y., Lin, C.-K., Zheng, G.-L., Cheng, Z.-Y., You, H., Wang, W.-D. & Lin, J. (2006). Chem. Mater. 18, 3463-3469.  [Web of Science] [CSD] [CrossRef] [ChemPort]
Liu, Q.-K., Ma, J.-P. & Dong, Y.-B. (2010). J. Am. Chem. Soc. 132, 7005-7017.  [Web of Science] [CSD] [CrossRef] [ChemPort] [PubMed]
Liu, Q.-K., Ma, J.-P. & Dong, Y.-B. (2011). Chem. Commun. 47, 12343-12345.  [CSD] [CrossRef] [ChemPort]
Satapathy, R., Wu, Y. H. & Lin, H. C. (2012). Org. Lett. 14, 2564-2567.  [Web of Science] [CrossRef] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Sun, L., Li, G.-Z., Xu, M.-H., Li, X.-J., Li, J. R. & Deng, H. (2012). Eur. J. Inorg. Chem. pp. 1764-1772.  [Web of Science] [CSD] [CrossRef]
Zheng, Z., Yu, Z.-P., Yang, M.-D., Jin, F., Zhang, Q., Zhou, H.-P., Wu, J.-Y. & Tian, Y.-P. (2013). J. Org. Chem. 78, 3222-3234.  [CrossRef] [ChemPort] [PubMed]
Zhou, H.-P., Yin, J.-H., Zheng, L.-X., Wang, P., Hao, F.-Y., Geng, W.-Q., Gan, X.-P., Xu, G.-Y., Wu, J.-Y., Tian, Y.-P., Tao, X.-T., Jiang, M.-H. & Kan, Y.-H. (2009). Cryst. Growth Des. 9, 3789-3798.  [CSD] [CrossRef] [ChemPort]


Acta Cryst (2013). E69, m556-m557   [ doi:10.1107/S160053681302518X ]

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