Bis[4-amino-N-(pyrimidin-2-yl)benzene­sulfonamidato](2,2′-bipyridine)manganese(II)

Tian-Jing He; Yan-Shu Tan; Yun-Qiong Gu; Zhen-Feng Chen; Hong Liang

doi:10.1107/S1600536810017794

. 2010 May 22;66(Pt 6):m684–m685. doi: 10.1107/S1600536810017794

Bis[4-amino-N-(pyrimidin-2-yl)benzenesulfonamidato](2,2′-bipyridine)manganese(II)

Tian-Jing He ^a, Yan-Shu Tan ^a, Yun-Qiong Gu ^a, Zhen-Feng Chen ^a,^*, Hong Liang ^a

PMCID: PMC2979398 PMID: 21579324

Abstract

The title compound, [Mn(C₁₀H₉N₄O₂S)₂(C₁₀H₈N₂)], contains a distorted octahedral [Mn(sdz)₂(bpy)] (sdz is the sulfadiazine anion and bpy is 2,2′-bipyridine) complex molecule. A three-dimensional network is generated by N—H⋯N, N—H⋯O and C—H⋯O hydrogen bonds from the sulfadiazine ligands.

Related literature

For mono-ligand sulfadiazine–metal complexes, see: Yuan et al. (2001 ▶); Wang et al. (2005 ▶). For mixed-ligand sulfadiazine–metal complexes, see: Ajibade et al. (2006 ▶); Brown et al. (1987 ▶); Hossain et al. (2006 ▶); Wang et al. (2009 ▶, 2010 ▶). For 2,2′-bipyridine–Mn(II) complexes, see: Chen et al. (1995 ▶); Cheng et al. (2004 ▶).

Experimental

Crystal data

[Mn(C₁₀H₉N₄O₂S)₂(C₁₀H₈N₂)]
M _r = 709.67
Monoclinic,
a = 20.121 (3) Å
b = 17.555 (3) Å
c = 17.956 (3) Å
β = 106.973 (4)°
V = 6066.4 (17) Å³
Z = 8
Mo Kα radiation
μ = 0.63 mm⁻¹
T = 193 K
0.25 × 0.17 × 0.15 mm

Data collection

Rigaku Mercury CCD diffractometer
Absorption correction: multi-scan (REQAB; Jacobson, 1998 ▶) T _min = 0.859, T _max = 0.912
28490 measured reflections
5533 independent reflections
4438 reflections with I > 2σ(I)
R _int = 0.077

Refinement

R[F ² > 2σ(F ²)] = 0.073
wR(F ²) = 0.167
S = 1.17
5533 reflections
441 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.43 e Å⁻³
Δρ_min = −0.58 e Å⁻³

Data collection: CrystalClear (Rigaku, 1999 ▶); cell refinement: CrystalClear; data reduction: CrystalStructure (Rigaku/MSC & Rigaku, 2000 ▶); 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 datablocks I, global. DOI: 10.1107/S1600536810017794/hg2677sup1.cif

e-66-0m684-sup1.cif^{(31KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810017794/hg2677Isup2.hkl

e-66-0m684-Isup2.hkl^{(271KB, 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
N8—H8B⋯O2ⁱ	0.87 (6)	2.17 (6)	3.011 (6)	163 (5)
N4—H4A⋯N3ⁱⁱ	0.82 (5)	2.23 (5)	3.003 (6)	156 (5)
C12—H12⋯O1ⁱⁱⁱ	0.95	2.32	3.248 (6)	165

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

Acknowledgments

The authors thank the Guangxi Natural Science Foundation of China (No. 0991003, 2010GXNSFF013001) and the Open Foundation of the Key Laboratory for the Chemistry and Molecular Engineering of Medicinal Resources (Ministry of Education of China) for financial support.

supplementary crystallographic information

Comment

In the title compound, [Mn(sdz)₂(bpy)] (where sdz is the sulfadiazine anion and bpy is 2,2'-bipyridine), the Mn(II) ion has six-coordinated distorted octahedral geometry and contains two bidentate N-coordinated sulfadiazinate anions and one chelating 2,2'-bipyridine ligand. The coordination mode of sulfadiazine is similar to its cobalt(II) complex (Ajibade et al., 2006; Wang et al. 2010), nickel(II) complex (Wang et al.200 9), and copper(II) complex (Brown et al., 1987), but different from Zn(sdz)₂ (Yuan et al., 2001), polymeric Cd(II) complex (Wang et al. 2005), and its copper complex (Hossain et al. 2006). The Mn—N bond distances involving the sulfonamide atoms N1, N5,the pyrimido atoms N2, N6, and the 2,2'-bipyridine atoms N9, N10, are very similar, at 2.242 (4), 2.234 (4), 2.312 (4), 2.278 (4), 2.235 (4), 2.225 (4) Å, respectively. The bond distances of the chelating bpy to Mn(II), Mn—N are consistent with those for the reported bpy-Mn(II) complexes, e.g. diazidobis(2,2'-bipyridine)manganese(II) (Mn—N 2.322 (3) Å)(Cheng et al., 2004) and tris(2,2'-bipyridine)manganese(II) perchlorate hemihydrate (Mn—N 2.214 (4)-2.294 (4) Å)(Chen et al., 1995). The tetrahedral coordination at S is distorted, also found in the neutral sulfadiazine molecule. A three dimensional network is generated via N—H···N, N—H···O, C—H···O hydrogen bonds from the sulfadiazine ligands of the complex.

Experimental

0.1 mmol Mn(CH₃COO)₂.4H₂O, 0.2 mmol sulfadiazine, 0.1 mmol 2,2'-bipyridine, ethanol (1 ml), methanol (1 ml) and pyridine (0.1 ml) were placed in a Pyrex tube (ca 25 cm). The tube was frozen with liquid N₂, evacuated under vacuum, sealed with a torch and heated at 353 K for three days to give yellow block-shaped crystals, with a yield of 70%.