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

Lian-Ke Wang; Wei-Ju Zhu; Hong-Ping Zhou

doi:10.1107/S160053681302518X

. 2013 Sep 21;69(Pt 10):m556–m557. doi: 10.1107/S160053681302518X

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

Lian-Ke Wang ^a, Wei-Ju Zhu ^a, Hong-Ping Zhou ^a,^*

PMCID: PMC3790361 PMID: 24098183

Abstract

In the title complex, [HgI₂(C₂₁H₁₉N₅)₂], the Hg^II 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 π–π 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 ▶); Li et al. (2006 ▶); Liu et al. (2010 ▶, 2011 ▶); Satapathy et al. (2012 ▶); Sun et al. (2012 ▶). For the organic ligand of the title compound, see: Zheng et al. (2013 ▶). For related structures, see: Jin, Wang et al. (2013 ▶); Jin, Zhang et al. (2013 ▶); Zhou et al. (2009 ▶). graphic file with name e-69-0m556-scheme1.jpg

Experimental

Crystal data

[HgI₂(C₂₁H₁₉N₅)₂]
M _r = 1137.21
Monoclinic,
a = 38.9622 (16) Å
b = 5.5684 (12) Å
c = 21.9564 (14) Å
β = 117.738 (2)°
V = 4216.2 (10) Å³
Z = 4
Mo Kα radiation
μ = 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 ▶) T _min = 0.307, T _max = 0.457
14961 measured reflections
4078 independent reflections
3384 reflections with I > 2σ(I)
R _int = 0.032

Refinement

R[F ² > 2σ(F ²)] = 0.027
wR(F ²) = 0.071
S = 1.01
4078 reflections
251 parameters
H-atom parameters constrained
Δρ_max = 0.78 e Å⁻³
Δρ_min = −0.52 e Å⁻³

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: XP in SHELXTL and DIAMOND (Brandenburg, 1999 ▶); software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablock(s) I, Global. DOI: 10.1107/S160053681302518X/hy2634sup1.cif

e-69-0m556-sup1.cif^{(25.7KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681302518X/hy2634Isup2.hkl

e-69-0m556-Isup2.hkl^{(223.8KB, hkl)}

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

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

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Symmetry code: (i) Inline graphic .

Acknowledgments

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.

supplementary crystallographic information

1. Comment

The design and synthesis of metal-organic hybrid complexes based on strong coordinate bonds and multiple weak non-covalent forces have become one of the most active fields in coordination chemistry and crystal engineering not only for their fascinating structural features but also for their interesting properties as new functional materials with tremendous potential applications in the areas of luminescence, catalysis, separation, adsorption, biological chemistry (Haneda et al., 2007; Li et al., 2006; Liu et al., 2010, 2011; Satapathy et al., 2012; Sun et al., 2012). The organic ligand of the title compound had been investigated for its optical properties (Zheng et al., 2013). A variety of mercury(II) complexes have been reported (Jin, Wang et al., 2013). Besides, triazole and isophorone-malononitrile complexes have been reported (Jin, Zhang et al., 2013; Zhou et al., 2009). In this paper, we report the synthesis and crystal structure of the title complex (Fig. 1). In the crystal, intermolecular π–π interactions between the triazole and benzene rings [centroid–centroid distance = 3.794 (3) Å] link the molecules into a band extending in [010] (Fig. 2). The neighboring bands are further linked into a two-dimensional network parallel to (100) through C—H···N hydrogen bonds (Fig.3).

2. Experimental

For the preparation of the title complex, (E)-2-(3-(4-(1H-1,2,4-triazol-1-yl)styryl)- 5,5-dimethylcyclohex-2-enylidene)malononitrile (0.341 g, 1 mmol) in 25 ml of dichloromethane was added into a 50 ml colorimeter tube, carefully layered with a clear acetonitrile and benzene solution (25 ml) of HgI₂ (0.227 g, 0.5 mmol). Crystals were obtained by slow interlayer diffusion (yield: 0.427 g, 75.1%).