cis-Bis[4-amino-N-(pyrimidin-2-yl)benzene­sulfonamido-κ2 N,N′]bis­(dimethyl sulfoxide-κO)cadmium

G M Golzar Hossain

doi:10.1107/S1600536811010816

. 2011 Mar 26;67(Pt 4):m505–m506. doi: 10.1107/S1600536811010816

cis-Bis[4-amino-N-(pyrimidin-2-yl)benzenesulfonamido-κ² N,N′]bis(dimethyl sulfoxide-κO)cadmium

G M Golzar Hossain ^a,^*

PMCID: PMC3099781 PMID: 21754012

Abstract

The complete molecule of the title compound, [Cd(C₁₀H₉N₄O₂S)₂(C₂H₆OS)₂], is completed by the application of a twofold rotation axis. The Cd^II atom is six coordinated by two bidentate sulfadiazinate anions and two dimethylsulfoxide molecules. The resulting N₄O₂ donor set displays a distorted trigonal–prismatic coordination geometry. The S atom and methyl groups of dimethylsulfoxide are disordered over two sets of sites, with site occupancies of 0.715 (4) and 0.285 (4). The crystal structure features intermolecular N—H⋯N and N—H⋯O hydrogen bonds that lead to the formation of layers in the ab plane.

Related literature

For related structures, see: Heren et al. (2006 ▶); Hossain & Amoroso (2007 ▶). For background to hydrogen bonds formed by sulfadiazinate anions, see: Paşaoğlu et al. (2008 ▶).

Experimental

Crystal data

[Cd(C₁₀H₉N₄O₂S)₂(C₂H₆OS)₂]
M _r = 767.20
Orthorhombic,
a = 16.9168 (5) Å
b = 15.2448 (3) Å
c = 11.8402 (3) Å
V = 3053.51 (13) Å³
Z = 4
Mo Kα radiation
μ = 1.04 mm⁻¹
T = 150 K
0.22 × 0.20 × 0.18 mm

Data collection

Nonius KappaCCD diffractometer
Absorption correction: multi-scan (Blessing, 1995 ▶) T _min = 0.803, T _max = 0.835
21431 measured reflections
3503 independent reflections
2545 reflections with I > 2σ(I)
R _int = 0.088

Refinement

R[F ² > 2σ(F ²)] = 0.045
wR(F ²) = 0.102
S = 1.09
3503 reflections
235 parameters
30 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.74 e Å⁻³
Δρ_min = −0.78 e Å⁻³

Data collection: DENZO (Otwinowski & Minor, 1997 ▶) and COLLECT (Hooft, 1998 ▶); cell refinement: DENZO and COLLECT; data reduction: DENZO and COLLECT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); 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/S1600536811010816/tk2721sup1.cif

e-67-0m505-sup1.cif^{(22KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811010816/tk2721Isup2.hkl

e-67-0m505-Isup2.hkl^{(171.9KB, hkl)}

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

Table 1. Selected bond lengths (Å).

Cd1—O1	2.268 (3)
Cd1—N11	2.305 (3)
Cd1—N12	2.452 (3)

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

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N14—H14A⋯N13ⁱ	0.94 (3)	2.30 (3)	3.168 (5)	152 (4)
N14—H14B⋯O11ⁱⁱ	0.95 (3)	2.02 (3)	2.967 (5)	173 (4)

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

Acknowledgments

The author is grateful to the Ministry of Science and Information & Communication Technology for financial support and to the School of Chemistry, Cardiff University, Wales, for crystallographic services.

supplementary crystallographic information

Comment

In an attempt to prepare a complex of sulfadiazine with the cadmium(II) ion in methanol by the reaction of a cadmium salt and sulfadiazine followed by crystallization from dimethylsulfoxide, the compound isolated was shown by crystallography to have the formula [Cd(C₁₀H₉N₄O₂S)₂](DMSO)₂.

The six coordinate cadmium complex is trigonal prismatic, Fig. 1. The C18–N14 bond distance of 1.366 (5) Å and the C15–S11–N11–C11 torsion angle of 66.1 (3) ° are comparable to those observed in related structures (Heren et al., 2006; Hossain & Amoroso, 2007). The Cd—O bond distance is shorter than the Cd—N bonds (Table 1). The dihedral angle between the aromatic rings of the anion of 88.65 (12) ° and this is greater than value of 71.10 (14) ° in the sulfadiazinate anion (Hossain & Amoroso, 2007). This is because in the latter the molecule is not bonded to a metal ion. The packing of (I) (Fig. 2) is stabilized by intermolecular N—H···N and N—H···O hydrogen bonds (Table 2) occurring between the anions in accord with a literature precedent (Paşaoğlu, et al., 2008). This hydrogen bonding leads to layers in the ab plane, Fig. 2.

Experimental

The sodium salt of sulfadiazine (5.446 g, 2 mmol) was dissolved in hot methanol (50 ml) and a methanol solution (10 ml) of (CH₃COO)₂Cd.2H₂O (2.6647 g, 1 mmol) was added slowly with constant stirring on a hot plate. A white precipitate was formed and the mixture was stirred for a further 2 h. The precipitate was filtered off and dried over silica gel. It was then dissolved in dimethylsulfoxide solution (50 ml), Colourless blocks were filtered off and dried over silica gel.