(6,6′-Dimethyl-2,2′-bipyridine-κ2 N,N′)diiodidomercury(II)

Robabeh Alizadeh; Sara Seifi; Vahid Amani

doi:10.1107/S1600536811004041

. 2011 Feb 5;67(Pt 3):m305. doi: 10.1107/S1600536811004041

(6,6′-Dimethyl-2,2′-bipyridine-κ² N,N′)diiodidomercury(II)

Robabeh Alizadeh ^a,^*, Sara Seifi ^a, Vahid Amani ^b

PMCID: PMC3052018 PMID: 21522242

Abstract

In the title complex, [HgI₂(C₁₂H₁₂N₂)], the Hg^II atom has a distorted tetrahedral coordination formed by two N atoms of the 6,6′-dimethyl-2,2′-bipyridine ligand and two terminal I atoms [N—Hg—N = 70.1 (2) and I—Hg—I = 130.59 (3)°]. The crystal packing features π–π contacts between the pyridine rings of adjacent molecules [centroid–centroid distance = 3.773 (5) Å] and also between a pyridine ring of one molecule and the five-membered chelate ring of an adjacent molecule [centroid–centroid distance = 3.668 (4) Å].

Related literature

For the structures of metal complexes with a 6,6′-dimethyl-2,2′-bipyridine ligand, see: Akbarzadeh Torbati et al. (2010 ▶); Alizadeh et al. (2010 ▶); Alizadeh, Kalateh, Ebadi et al. (2009 ▶); Alizadeh, Kalateh, Khoshtarkib et al. (2009 ▶); Alizadeh, Khoshtarkib et al. (2009 ▶); Itoh et al. (2005 ▶); Kou et al. (2008 ▶); Onggo et al. (2005 ▶).

Experimental

Crystal data

[HgI₂(C₁₂H₁₂N₂)]
M _r = 638.63
Monoclinic,
a = 8.8096 (18) Å
b = 12.025 (2) Å
c = 14.693 (3) Å
β = 101.88 (3)°
V = 1523.2 (5) Å³
Z = 4
Mo Kα radiation
μ = 14.14 mm⁻¹
T = 298 K
0.16 × 0.15 × 0.12 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T _min = 0.128, T _max = 0.186
9361 measured reflections
4057 independent reflections
3409 reflections with I > 2σ(I)
R _int = 0.051

Refinement

R[F ² > 2σ(F ²)] = 0.040
wR(F ²) = 0.095
S = 1.10
4057 reflections
154 parameters
H-atom parameters constrained
Δρ_max = 1.22 e Å⁻³
Δρ_min = −1.23 e Å⁻³

Data collection: APEX2 (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: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811004041/ya2136sup1.cif

e-67-0m305-sup1.cif^{(16.9KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811004041/ya2136Isup2.hkl

e-67-0m305-Isup2.hkl^{(194.8KB, hkl)}

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

Table 1. Selected bond lengths (Å).

N1—Hg1	2.380 (5)
N2—Hg1	2.381 (6)
I1—Hg1	2.6503 (10)
I2—Hg1	2.6876 (7)

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Acknowledgments

The authors are grateful to Damghan University for financial support.

supplementary crystallographic information

Comment

6,6'-Dimethyl-2,2'-bipyridine (6,6'-dmbipy) is a rather widely used bidentate ligand, and complexes of different metals with 6,6'-dmbipy have been prepared, e.g. those of cobalt (Akbarzadeh Torbati et al., 2010),cadmium (Alizadeh et al., 2010),zinc (Alizadeh, Kalateh, Ebadi et al., 2009; Alizadeh, Kalateh, Khoshtarkib et al., 2009; Alizadeh, Khoshtarkib et al., 2009), copper (Itoh et al., 2005), nickel (Kou et al., 2008), and ruthenium (Onggo et al., 2005). We report herein the synthesis and first crystal structure of the mercury complex of this ligand (Fig. 1).

The Hg1 atom has a distorted tetrahedral coordination formed by atoms N1 and N2 of the 6,6'-dimethyl-2,2'-bipyridine ligand and terminal I1 and I2 atoms [N—Hg—N 70.1 (2)°; I—Hg—I 130.59 (3)°; see Table 1 for bond lengths involving Hg1].

In the crystal structure, intermolecular /p-/p contacts (Fig. 2) between the pyridine rings and also between pyridine ring and chelate ring of the adjacent molecules may stabilize the structure: the centroid-centroid distances Cg1—Cg2ⁱ and Cg2—Cg3ⁱ are equal to 3.668 (4) and 3.773 (5)Å respectively [Cg1, Cg2 and Cg3 represent centroids of the rings (Hg1/N1/C6/C7/N2), (N1/C2—C6), and (N2/C7—C11); symmetry code (i): 2 - x,1 - y,-z].

Experimental

For the preparation of the title compound, a solution of 6,6'-dimethyl-2,2'-bipyridine (0.28 g, 1.50 mmol) in acetonitrile (10 ml) was added to a solution of HgI₂ (0.68 g, 1.50 mmol) in methanol (10 ml), and the resulting colorless mixture was stirred for 30 min at 313 K. It was then left to evaporate slowly at room temperature. After six days, colorless prismatic crystals of the title compound, suitable for X-ray diffraction experiment, were isolated (yield 0.71 g; 74.1%).