Dibromido(dimethyl sulfoxide-κO)(6-methyl-2,2′-bipyridine-κ2 N,N′)cadmium

Sadif A Shirvan; Sara Haydari Dezfuli

doi:10.1107/S1600536812033168

. 2012 Jul 28;68(Pt 8):m1124. doi: 10.1107/S1600536812033168

Dibromido(dimethyl sulfoxide-κO)(6-methyl-2,2′-bipyridine-κ² N,N′)cadmium

Sadif A Shirvan ^a,^*, Sara Haydari Dezfuli ^a

PMCID: PMC3414166 PMID: 22904773

Abstract

In the title compound, [CdBr₂(C₁₁H₁₀N₂)(C₂H₆OS)], the Cd^II atom is five-coordinated in a distorted trigonal–bipyramidal geometry by two N atoms from a 6-methyl-2,2′-bipyridine ligand, one O atom from a dimethyl sulfoxide ligand and two Br atoms. An intramolecular C—H⋯O hydrogen bond occurs. The crystal structure is stabilized by C—H⋯Br hydrogen bonds and π–π contacts between the pyridine rings [centroid–centroid distances = 3.582 (5) and 3.582 (5) Å].

Related literature

For related structures, see: Ahmadi et al. (2009 ▶); Ahmadi, Ebadi et al. (2008 ▶); Ahmadi, Kalateh et al. (2008 ▶); Alizadeh et al. (2009 ▶); Amani et al. (2009 ▶); Kalateh et al. (2010 ▶); Newkome et al. (1982 ▶); Onggo et al. (1990 ▶, 2005 ▶); Shirvan & Haydari Dezfuli (2012a ▶,b ▶).

Experimental

Crystal data

[CdBr₂(C₁₁H₁₀N₂)(C₂H₆OS)]
M _r = 520.56
Monoclinic,
a = 9.0169 (6) Å
b = 14.5503 (8) Å
c = 14.1473 (8) Å
β = 106.561 (5)°
V = 1779.11 (18) Å³
Z = 4
Mo Kα radiation
μ = 5.83 mm⁻¹
T = 293 K
0.40 × 0.35 × 0.30 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T _min = 0.070, T _max = 0.240
14429 measured reflections
3487 independent reflections
2683 reflections with I > 2σ(I)
R _int = 0.114

Refinement

R[F ² > 2σ(F ²)] = 0.059
wR(F ²) = 0.175
S = 1.05
3487 reflections
181 parameters
H-atom parameters constrained
Δρ_max = 1.35 e Å⁻³
Δρ_min = −1.58 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 ▶); software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812033168/hy2573sup1.cif

e-68-m1124-sup1.cif^{(18.8KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812033168/hy2573Isup2.hkl

e-68-m1124-Isup2.hkl^{(171KB, 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
C11—H11⋯O1	0.93	2.35	3.003 (12)	127
C13—H13C⋯Br2ⁱ	0.96	2.89	3.722 (15)	146

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Symmetry code: (i) Inline graphic .

Acknowledgments

We are grateful to the Islamic Azad University, Omidieh Branch, for financial support.

supplementary crystallographic information

Comment

Recently, we reported the synthesis and crystal structures of [Cd(5,5'-dmbpy)(µ-Br)₂]_n (Shirvan & Haydari Dezfuli, 2012a) and [CdBr₂(4,4'-dmbpy)(DMSO)] (Shirvan & Haydari Dezfuli, 2012b) (5,5'-dmbpy = 5,5'-dimethyl-2,2'-bipyridine, 4,4'-dmbpy = 4,4'-dimethyl-2,2'-bipyridine, DMSO = dimethyl sulfoxide). 6-Methyl-2,2'-bipyridine (6-mbipy) is a good ligand and a few complexes with 6-mbipy have been prepared, such as that of mercury (Ahmadi, Ebadi et al., 2008), platinum (Amani et al., 2009), lead (Ahmadi et al., 2009), palladium (Newkome et al., 1982), iron (Onggo et al., 1990), ruthenium (Onggo et al., 2005) and zinc (Ahmadi, Kalateh et al., 2008; Alizadeh et al., 2009; Kalateh et al., 2010). Here, we report the synthesis and structure of the title compound.

In the title compound (Fig. 1), the Cd^II atom is five-coordinated in a distorted trigonal-bipyramidal geometry by two N atoms from one 6-methyl-2,2'-bipyridine ligand, one O atom from one dimethyl sulfoxide ligand and two Br atoms. In the crystal, intermolecular C—H···Br hydrogen bonds (Table 1, Fig. 2) and π–π contacts between the pyridine rings, Cg2···Cg3ⁱ and Cg3···Cg3ⁱⁱ, with centroid–centroid distances of 3.582 (5) and 3.582 (5) Å [symmetry codes: (i) -x, -y, 1-z; (ii) 1-x, -y, 1-z. Cg2 and Cg3 are the centroids of the N1/C2–C6 and N2/C7–C11 rings], stabilize the structure.

Experimental

For the preparation of the title compound, a solution of 6-methyl-2,2'-bipyridine (0.23 g, 1.33 mmol) in methanol (10 ml) was added to a solution of CdBr₂.4H₂O (0.46 g, 1.33 mmol) in methanol (10 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, 75.1%).