Dibromido(2,2′-dimethyl-4,4′-bi-1,3-thia­zole-κ2 N,N′)mercury(II)

Anita Abedi

doi:10.1107/S1600536810051494

. 2010 Dec 15;67(Pt 1):m76–m77. doi: 10.1107/S1600536810051494

Dibromido(2,2′-dimethyl-4,4′-bi-1,3-thiazole-κ² N,N′)mercury(II)

Anita Abedi ^a,^*

PMCID: PMC3050124 PMID: 21522594

Abstract

The asymmetric unit of the title compound, [HgBr₂(C₈H₈N₂S₂)], contains two crystallographically independent molecules. The Hg^II atoms are four-coordinated in a distorted tetrahedral geometry by two N atoms from a 2,2′-dimethyl-4,4′-bi-1,3-thiazole ligand and two Br atoms. In the crystal structure, intermolecular C—H⋯Br hydrogen bonds and π–π contacts between the thiazole rings [centroid–centroid distances = 3.670 (3) and 3.614 (2) Å] stabilize the structure.

Related literature

For metal complexes with 2,2′-dimethyl-4,4′-bithiazole ligands, see: Abedi & Yahyazade Bali (2010 ▶); Al-Hashemi et al. (2009 ▶, 2010 ▶); Khavasi et al. (2008 ▶); Notash et al. (2008 ▶, 2009 ▶). For related structures, see: Kalateh et al. (2008 ▶); Safari et al. (2009 ▶).

Experimental

Crystal data

[HgBr₂(C₈H₈N₂S₂)]
M _r = 556.69
Triclinic,
a = 10.2799 (6) Å
b = 11.1595 (7) Å
c = 11.6821 (7) Å
α = 88.4456 (11)°
β = 85.3290 (11)°
γ = 77.1162 (11)°
V = 1302.02 (14) Å³
Z = 4
Mo Kα radiation
μ = 18.25 mm⁻¹
T = 100 K
0.14 × 0.12 × 0.08 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T _min = 0.070, T _max = 0.240
20881 measured reflections
6912 independent reflections
5865 reflections with I > 2σ(I)
R _int = 0.041

Refinement

R[F ² > 2σ(F ²)] = 0.026
wR(F ²) = 0.062
S = 0.94
6912 reflections
275 parameters
H-atom parameters constrained
Δρ_max = 1.28 e Å⁻³
Δρ_min = −1.68 e Å⁻³

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶) and Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810051494/hy2386sup1.cif

e-67-00m76-sup1.cif^{(21KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810051494/hy2386Isup2.hkl

e-67-00m76-Isup2.hkl^{(338.2KB, hkl)}

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

Table 1. Selected bond lengths (Å).

Hg1—N1	2.379 (4)
Hg1—N2	2.383 (4)
Hg1—Br1	2.4970 (5)
Hg1—Br2	2.5206 (5)
Hg2—N3	2.357 (4)
Hg2—N4	2.410 (4)
Hg2—Br3	2.4999 (5)
Hg2—Br4	2.4957 (5)

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Table 2. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8B⋯Br4ⁱ	0.98	2.92	3.826 (5)	155
C10—H10A⋯Br4ⁱ	0.95	2.92	3.760 (5)	148
C16—H16B⋯Br3ⁱⁱ	0.98	2.87	3.772 (5)	154
C16—H16C⋯Br2ⁱⁱⁱ	0.98	2.88	3.837 (5)	165

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Symmetry codes: (i) Inline graphic ; (ii) ; (iii) .

Acknowledgments

The author is grateful to the Islamic Azad University, North Tehran Branch, for financial support.

supplementary crystallographic information

Comment

Recently, we reported the synthesis and crystal structure of [HgI₂(dm4bt)] (dm4bt is 2,2'-dimethyl-4,4'-bithiazole) (Abedi & Yahyazade Bali, 2010). Dm4bt is a good bidentate ligand, and numerous complexes with dm4bt have been prepared, such as that of zinc (Khavasi et al., 2008), thallium (Notash et al., 2008), cadmium (Notash et al., 2009) and copper (Al-Hashemi et al., 2009, 2010). For further investigation of dm4bt, we synthesis the title complex and report herein its crystal structure.

The asymmetric unit of the title compound (Fig. 1) contains two crystallographically independent molecules. The Hg^II atom is four-coordinated in a distorted tetrahedral configuration by two N atoms from a dm4bt ligand and two Br atoms. The Hg—N and Hg—Br bond lengths (Table 1) and angles are within normal range found in [Hg(SCN)₂(dm4bt)] (Safari et al., 2009) and {HgBr₂[NH(py)₂]} [NH(py)₂ is di-2-pyridylamine] (Kalateh et al., 2008).

In the crystal structure, intermolecular C—H···Br hydrogen bonds (Table 2) and π–π contacts (Fig. 2) between the thiazole rings, Cg1···Cg2ⁱ and Cg3···Cg4ⁱⁱ [symmetry codes: (i) 2-x, 1-y, -z; (ii) 1-x, 2-y, 1-z. Cg1, Cg2, Cg3 and Cg4 are the centroids of the rings S1/C1/N1/C3/C2, S2/C4/N2/C6/C5, S3/C9/N3/C11/C10 and S4/C12/N4/C14/C13, respectively] stabilize the structure, with centroid–centroid distances of 3.670 (3) and 3.614 (2) Å.

Experimental

For the preparation of the title compound, a solution of dm4bt (0.26 g, 1.3 mmol) in methanol (15 ml) was added to a solution of HgBr₂ (0.47 g, 1.3 mmol) in methanol (15 ml) at room temperature. Crystals suitable for X-ray diffraction experiment were obtained by methanol diffusion into a colorless solution in DMSO after one week (yield: 0.52 g, 71.8%).