trans-Bis[4-amino-N-(pyrimidin-2-yl-κN)benzene­sulfonamidato-κN]bis(N,N-dimethyl­formamide-κO)cobalt(II)

Jing Jing Guo; Wei Wang; Yi Dong Zhang; Li Yang; Shu Hua Zhang

doi:10.1107/S160053681204336X

. 2012 Oct 24;68(Pt 11):m1398–m1399. doi: 10.1107/S160053681204336X

trans-Bis[4-amino-N-(pyrimidin-2-yl-κN)benzenesulfonamidato-κN]bis(N,N-dimethylformamide-κO)cobalt(II)

Jing Jing Guo ^a, Wei Wang ^a, Yi Dong Zhang ^a, Li Yang ^a, Shu Hua Zhang ^a,^*

PMCID: PMC3515142 PMID: 23284369

Abstract

The title complex, [Co(C₁₀H₉N₄O₂S)₂(C₃H₇NO)₂], lies across an inversion center. The Co^II atom is coordinated in a slightly distorted octahedral geometry by four N atoms from two bidentate 4-amino-N-(pyrimidin-2-yl)benzenesulfonamidate (sulfadiazine) anions and two O atoms from two dimethylformamide (DMF) ligands. The dihedral angle between the benzene and pyrimidine rings is 82.37 (13)°. A three-dimensional network is generated by N—H⋯O hydrogen bonds between the amino groups and of the sulfonamidate O atoms of neighbouring molecules. The DMF ligand is disordered over two sets of sites in a 0.559 (4):0.441 (4) ratio.

Related literature

For background to sulfonamides, see: Connor (1998 ▶). For background to metal complexes of sulfadiazine, see: Wang et al. (2009 ▶, 2010 ▶); Ajibade et al. (2006 ▶); Hossain et al. (2011 ▶); Tommasino et al. (2011 ▶); Ghosh et al. (2011 ▶).

Experimental

Crystal data

[Co(C₁₀H₉N₄O₂S)₂(C₃H₇NO)₂]
M _r = 703.67
Monoclinic,
a = 8.9008 (6) Å
b = 11.2078 (6) Å
c = 16.5565 (9) Å
β = 102.147 (6)°
V = 1614.67 (16) Å³
Z = 2
Mo Kα radiation
μ = 0.72 mm⁻¹
T = 298 K
0.28 × 0.25 × 0.20 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T _min = 0.815, T _max = 0.869
13220 measured reflections
3495 independent reflections
2989 reflections with I > 2σ(I)
R _int = 0.028

Refinement

R[F ² > 2σ(F ²)] = 0.040
wR(F ²) = 0.095
S = 0.99
3495 reflections
222 parameters
36 restraints
H-atom parameters constrained
Δρ_max = 0.33 e Å⁻³
Δρ_min = −0.35 e Å⁻³

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); 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

Click here for additional data file.^{(22.2KB, cif)}

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S160053681204336X/wm2693sup1.cif

e-68-m1398-sup1.cif^{(22.2KB, cif)}

Click here for additional data file.^{(178.3KB, hkl)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681204336X/wm2693Isup2.hkl

e-68-m1398-Isup2.hkl^{(178.3KB, hkl)}

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

Table 1. Selected bond lengths (Å).

Co1—O1	2.065 (19)
Co1—N1	2.121 (2)
Co1—N2	2.1460 (18)

Open in a new tab

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

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N4—H4B⋯O3ⁱ	0.86	2.31	3.112 (3)	155
N4—H4C⋯O3ⁱⁱ	0.86	2.27	2.951 (3)	136

Open in a new tab

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

Acknowledgments

This work was supported financially by the National Natural Science Foundation of China (No. 21161006), the Innovation Project of Guangxi Graduate Education (2010105960817M03) and by the doctoral start-up research fund of Guilin University of Technology (to SHZ).

supplementary crystallographic information

Comment

Sulfonamides are among the most widely used antibacterial agents (Connor, 1998), because of their low cost, low toxicity, and excellent activity against bacterial diseases. Sulfadiazine, or 4-amino-N-pyrimidin-2-yl-benzenesulfonamide, is a sulfanilamide antibiotic and its metal complexes have been studied previously (Wang et al. 2009, 2010; Ajibade et al., 2006; Hossain et al., 2011; Tommasino et al., 2011; Ghosh et al., 2011). The crystal structure of the title compound, [Co(C₁₀H₉N₄O₂S)₂(C₃H₇NO)₂], a cobalt sulfadiazine complex with additional dimethylformamide ligands, (I), is presented herein.

The molecular structure of (I) is shown in Fig. 1. The Co^II ion lies on a centre of inversion and is coordinated by four N atoms from two symmetry-related 4-amino-N-pyrimidin-2-yl-benzenesulfonamidate anions and two O atoms from two dimethylformamide ligands, forming a slightly distorted octahedral N₄O₂ geometry (Table 1). The dihedral angle between the phenyl and pyrimidine rings is 82.37 (13) °. A three-dimensional hydrogen-bonded network is generated by N—H···O interactions (Table 2; Fig.2).

Experimental

Complex (I) was prepared from a mixture of sulfadiazine (1 mmol, 0.250 g), Co(NO₃)₂^.6H₂O (0.5 mmol, 0.145 g), triethylamine (0.5 ml) and N,N-dimethylformamid (8 ml) sealed in a 15 ml teflon-lined stainless steel bomb, and kept at 373 K for 96 h under autogenous pressure. After the reaction was slowly cooled to room temperature, red block-like crystals were obtained (yield: 72% based on cobalt). Anal./calc. for C₂₆H₃₂N₁₀CoO₆S₂(%): C 44.38; H 4.58; N 19.90. Found(%): C 44.34; H 4.61; N 19.95.