(5,5′-Dimethyl-2,2′-bipyridine-κ2 N,N′)diiodidomercury(II)

Nasim Tadayon Pour; Amin Ebadi; Anita Abedi; Vahid Amani; Hamid Reza Khavasi

doi:10.1107/S160053680802953X

. 2008 Sep 20;64(Pt 10):m1305. doi: 10.1107/S160053680802953X

(5,5′-Dimethyl-2,2′-bipyridine-κ² N,N′)diiodidomercury(II)

Nasim Tadayon Pour ^a, Amin Ebadi ^b, Anita Abedi ^c, Vahid Amani ^a,^*, Hamid Reza Khavasi ^d

PMCID: PMC2959332 PMID: 21201044

Abstract

In the molecule of the title compound, [HgI₂(C₁₂H₁₂N₂)], the Hg^II atom is four-coordinated in a distorted tetrahedral configuration by two N atoms from 5,5′-dimethyl-2,2′-bipyridine and two I atoms. There is a π–π contact between pyridine rings of adjacent molecules [centroid–centroid distance = 3.723 (5) Å].

Related literature

For related literature, see: Ahmadi, Kalateh et al. (2008 ▶); Ahmadi, Khalighi et al. (2008 ▶); Chen et al. (2006 ▶); Freire et al. (1999 ▶); Htoon & Ladd (1976 ▶); Khalighi et al. (2008 ▶); Khavasi et al. (2008 ▶); Yousefi, Khalighi, et al. (2008 ▶); Yousefi, Tadayon Pour et al. (2008 ▶).

Experimental

Crystal data

[HgI₂(C₁₂H₁₂N₂)]
M _r = 638.63
Orthorhombic,
a = 15.0325 (8) Å
b = 15.0654 (8) Å
c = 14.0579 (10) Å
V = 3183.7 (3) Å³
Z = 8
Mo Kα radiation
μ = 13.53 mm⁻¹
T = 298 (2) K
0.35 × 0.31 × 0.20 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: numerical [shape of crystal determined optically (X-SHAPE and X-RED32; Stoe & Cie (2005) ▶] T _min = 0.015, T _max = 0.075
23007 measured reflections
4306 independent reflections
3418 reflections with I > 2σ(I)
R _int = 0.083

Refinement

R[F ² > 2σ(F ²)] = 0.055
wR(F ²) = 0.124
S = 1.19
4306 reflections
154 parameters
H-atom parameters constrained
Δρ_max = 1.44 e Å⁻³
Δρ_min = −1.51 e Å⁻³

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT (Bruker, 1998 ▶); 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. DOI: 10.1107/S160053680802953X/hk2531sup1.cif

e-64-m1305-sup1.cif^{(17.1KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S160053680802953X/hk2531Isup2.hkl

e-64-m1305-Isup2.hkl^{(206.8KB, hkl)}

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

Table 1. Selected geometric parameters (Å, °).

Hg1—I1	2.6587 (9)
Hg1—I2	2.6684 (8)
Hg1—N1	2.377 (7)
Hg1—N2	2.389 (6)

Open in a new tab

I1—Hg1—I2	129.89 (3)
N1—Hg1—I1	113.59 (16)
N1—Hg1—N2	69.7 (2)
N1—Hg1—I2	106.53 (16)
N2—Hg1—I1	107.15 (15)
N2—Hg1—I2	114.22 (15)

Open in a new tab

Acknowledgments

We are grateful to the Islamic Azad University, Shahr-e-Rey Branch, for financial support.

supplementary crystallographic information

Comment

Recently, we reported the syntheses and crystal structures of [Zn(5,5'-dmbpy)Cl₂], (II), (Khalighi et al., 2008), [Zn(6-mbpy)Cl₂], (III), (Ahmadi, Kalateh et al., 2008), [Cd(5,5'-dmbpy)(µ-Cl)₂]_n, (IV), (Ahmadi, Khalighi et al., 2008), [Cu(5,5'-dcbpy)(en)(H₂O)₂].2.5H₂O, (V), (Yousefi, Khalighi et al., 2008) and {[HgCl(dm4bt)]₂(µ-Cl)₂}, (VI), (Khavasi et al., 2008) [where 5,5'-dmbpy is 5,5'-dimethyl-2,2'-bipyridine, 6-mbpy is 6-methyl-2,2' -bipyridine, 5,5'-dcbpy is 2,2'-bipyridine-5,5'-dicarboxylate, en is ethylene- diamine and dm4bt is 2,2'-dimethyl-4,4'-bithiazole]. There are several Hg^II complexes, with formula, [HgI₂(N—N)], such as [HgI₂(bipy)], (VII), [HgI₂(phen)], (VIII) and [HgI₂(2,9-dmphen)], (IX), (Freire et al., 1999), [HgI₂(bipy)][HgI₂], (X), (Chen et al., 2006), [HgI₂(4,4'-dmbpy)], (XI), (Yousefi, Tadayon Pour et al., 2008) and [HgI₂(TMDA)], (XII), (Htoon & Ladd, 1976) [where bipy is 2,2'-bipyridine, phen is 1,10-phenanthroline, dmphen is 2,9-dimethyl-1,10-phenanthroline, 4,4'-dmbpy is 4,4'-dimethyl-2,2'-bipyridine and TMDA is tetramethylethylene- diamine] have been synthesized and characterized by single-crystal X-ray diffraction methods. We report herein the synthesis and crystal structure of the title compound, (I).

In the title compound, (Fig. 1), the Hg^II atom is four-coordinated in a distorted tetrahedral configuration by two N atoms from 5,5'-dimethyl-2,2'-bi- pyridine and two I atoms. The Hg—I and Hg—N bond lengths and angles (Table 1) are within normal ranges, as in (VII), (VIII) and (XI).

In the crystal structure, the π-π contact (Fig. 2) between the pyridine rings, Cg2···Cg3ⁱ [symmetry code: (i) x, 1 - y, 1 - z, where Cg2 and Cg3 are centroids of the rings (N1/C1/C2/C4-C6) and (N2/C7-C10/C12), respectively] may stabilize the structure, with centroid-centroid distance of 3.723 (5) Å.

Experimental

For the preparation of the title compound, (I), a solution of 5,5'-dimethyl -2,2'-bipyridine (0.25 g, 1.33 mmol) in methanol (10 ml) was added to a solution of HgI₂ (0.61 g, 1.33 mmol) in methanol (5 ml) at room temperature. The suitable crystals for X-ray analysis were isolated after one week by methanol diffusion to a colorless solution in DMSO (yield; 0.62 g, 72.9%).