Tetra­aqua­bis[3-(2-pyridylsulfan­yl)propionato N-oxide]nickel(II)

B Ravindran Durai Nayagam; Samuel Robinson Jebas; J P Edward Rajkumar; Dieter Schollmeyer

doi:10.1107/S1600536809011283

. 2009 Mar 31;65(Pt 4):m470. doi: 10.1107/S1600536809011283

Tetraaquabis[3-(2-pyridylsulfanyl)propionato N-oxide]nickel(II)

B Ravindran Durai Nayagam ^a,^*, Samuel Robinson Jebas ^b, J P Edward Rajkumar ^c, Dieter Schollmeyer ^d

PMCID: PMC2968857 PMID: 21582400

Abstract

In the centrosymmetric title compound, [Ni(C₈H₈NO₃S)₂(H₂O)₄], the Ni^II ion, which lies on an inversion centre, is six coordinated by four water molecules and two propionate O atoms from two 2-pyridylsulfanylpropionate N-oxide ligands, forming a slightly distorted octahedral geometry. An intramolecular O—H⋯O hydrogen bond stabilizes the molecular conformation. The crystal packing is consolidated by intermolecular O—H⋯O and C—H⋯O hydrogen bonding.

Related literature

For the biological activities of N-oxide derivatives, see: Bovin et al. (1992 ▶); Katsuyuki et al. (1991 ▶). Leonard et al. (1955 ▶); Lobana & Bhatia (1989 ▶); Symons & West (1985 ▶). For related literature, see: Jebas et al. (2005 ▶); Ravindran et al. (2008 ▶).

Experimental

Crystal data

[Ni(C₈H₈NO₃S)₂(H₂O)₄]
M _r = 527.20
Triclinic,
a = 4.8155 (5) Å
b = 8.7650 (10) Å
c = 12.9560 (15) Å
α = 86.400 (2)°
β = 79.501 (2)°
γ = 84.929 (2)°
V = 534.98 (10) Å³
Z = 1
Mo Kα radiation
μ = 1.16 mm⁻¹
T = 173 K
0.35 × 0.28 × 0.07 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2008 ▶) T _min = 0.405, T _max = 0.492 (expected range = 0.759–0.922)
9627 measured reflections
2615 independent reflections
2501 reflections with I > 2σ(I)
R _int = 0.017

Refinement

R[F ² > 2σ(F ²)] = 0.020
wR(F ²) = 0.055
S = 1.05
2615 reflections
142 parameters
H-atom parameters constrained
Δρ_max = 0.40 e Å⁻³
Δρ_min = −0.36 e Å⁻³

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: APEX2; data reduction: APEX2; 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 and PLATON (Spek, 2009 ▶).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809011283/bt2915sup1.cif

e-65-0m470-sup1.cif^{(17.1KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809011283/bt2915Isup2.hkl

e-65-0m470-Isup2.hkl^{(128.4KB, hkl)}

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

Table 1. Selected bond lengths (Å).

Ni1—O13	2.0488 (8)
Ni1—O15	2.0644 (8)
Ni1—O14	2.0898 (8)
N1—O7	1.3154 (13)

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

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O14—H14A⋯O12	0.81	1.84	2.6248 (12)	162
O14—H14B⋯O15ⁱ	0.81	2.27	2.9517 (12)	142
O14—H14B⋯O13ⁱ	0.81	2.64	3.2316 (12)	131
O15—H15A⋯O7ⁱⁱ	0.82	1.83	2.6469 (12)	172
O15—H15B⋯O13ⁱⁱⁱ	0.83	1.83	2.6570 (11)	172
C4—H4⋯O12^iv	0.95	2.48	3.2044 (17)	133
C6—H6⋯O14^v	0.95	2.46	3.2515 (16)	140
C10—H10B⋯O12^vi	0.99	2.42	3.3910 (14)	167

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

supplementary crystallographic information

Comment

N-oxides and their derivatives show a broad spectrum of biological activity such as antifungal, antimicrobial and antibacterial activities (Lobana & Bhatia, 1989; Symons & West, 1985). These compounds are also found to be involved in DNA strand scission under physiological conditions (Katsuyuki et al., 1991; Bovin et al., 1992). Pyridine N–oxides bearing a sulfur group in position two display significant antimicrobial activity (Leonard et al., 1955). In view of the importance of N–oxides, we have previously reported the crystal structures of N–oxide derivatives (Jebas et al., 2005; Ravindran et al., 2008). As an extension of our work on N–oxide derivatives, we report here the crystal structure of the title compound.

The asymmetric unit comprises of half molecule of the title compound, the other half is symmetry generated [symmetry code: -x + 1,-y + 1,-z + 1]. The Ni^II ion which lies on an inversion centre is six coordinated by four water molecules and two propianoto oxygen atoms from two 2-pyridylsulfanylpropionato N-oxide ligands forming a slightly distorted octahedral geometry. The bond lengths and angles agree well with the N–oxide derivatives reported earlier (Jebas et al., 2005)

Intramolecular O—H···O hydrogen bonding influences the conformation of the molecule. The crystal packing (Fig. 2) is consolidated by intermolecular O—H···O and C—H···O hydrogen bonding together with intramolecular S···O = 2.6968 (10) Å; O···O = 2.6248 (12) Å, intermolecular O···Oⁱ = 2.6469 (12) Å; O···Oⁱⁱ = 2.6570 (12) Å and O···Oⁱⁱⁱ = 2.9455 (12) Å [symmetry code: (i):1 + x,y,-1 + z; (ii) 2 - x,1 - y,1 - z; (iii) 1 - x,1 - y,1 - z] short contacts. The molecules are stacked along the a axis.

Experimental

A mixture of the potassium salt of 3(1-oxo-pyridinine- 2-sulfanyl)propionic acid (0.237 g,1 mmol) and Nickel (II) chloride (0.13 g, 0.5 mmol), in water (20 ml) was heated at 333k with continous stirring for one hour. The solution was kept aside for slow evaporation. After two weeks, green colored crystals were obtained.