Tetra-aqua-bis[3-(2-pyridylsulfan-yl)propionato N-oxide]nickel(II).

In the centrosymmetric title compound, [Ni(C(8)H(8)NO(3)S)(2)(H(2)O)(4)], the Ni(II) ion, which lies on an inversion centre, is six coordinated by four water mol-ecules and two propionate O atoms from two 2-pyridylsulfanylpropionate N-oxide ligands, forming a slightly distorted octa-hedral geometry. An intra-molecular O-H⋯O hydrogen bond stabilizes the mol-ecular conformation. The crystal packing is consolidated by inter-molecular 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 = 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

Δρmax = 0.40 e Å−3

Δρmin = −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 ▶).

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

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

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

[Ni(C8H8NO3S)2(H2O)4]	Z = 1
Mr = 527.20	F(000) = 274
Triclinic, P1	Dx = 1.636 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71069 Å
a = 4.8155 (5) Å	Cell parameters from 6946 reflections
b = 8.765 (1) Å	θ = 2.3–28.2°
c = 12.9560 (15) Å	µ = 1.16 mm−1
α = 86.400 (2)°	T = 173 K
β = 79.501 (2)°	Plate, green
γ = 84.929 (2)°	0.35 × 0.28 × 0.07 mm
V = 534.98 (10) Å3

Bruker SMART APEXII CCD diffractometer	2615 independent reflections
Radiation source: sealed Tube	2501 reflections with I > 2σ(I)
graphite	Rint = 0.017
CCD scan	θmax = 28.2°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 2008)	h = −6→6
Tmin = 0.405, Tmax = 0.492	k = −11→11
9627 measured reflections	l = −17→17

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.020	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.055	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0294P)2 + 0.2035P] where P = (Fo2 + 2Fc2)/3
2615 reflections	(Δ/σ)max < 0.001
142 parameters	Δρmax = 0.40 e Å−3
0 restraints	Δρmin = −0.36 e Å−3

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq
Ni1	0.5000	0.5000	0.5000	0.01405 (6)
N1	1.2267 (2)	0.77325 (12)	−0.20598 (8)	0.0197 (2)
C2	1.0696 (2)	0.79224 (13)	−0.10776 (8)	0.0167 (2)
C3	0.8347 (3)	0.89789 (14)	−0.09608 (9)	0.0212 (2)
H3	0.7229	0.9119	−0.0285	0.025*
C4	0.7627 (3)	0.98279 (15)	−0.18222 (10)	0.0254 (3)
H4	0.6027	1.0555	−0.1741	0.031*
C5	0.9266 (3)	0.96061 (16)	−0.28069 (10)	0.0291 (3)
H5	0.8794	1.0180	−0.3406	0.035*
C6	1.1567 (3)	0.85564 (16)	−0.29110 (10)	0.0274 (3)
H6	1.2685	0.8403	−0.3586	0.033*
O7	1.44740 (19)	0.67209 (11)	−0.21521 (7)	0.0264 (2)
S8	1.19805 (6)	0.67388 (3)	−0.01121 (2)	0.01821 (7)
C9	0.9142 (2)	0.70873 (14)	0.09994 (8)	0.0176 (2)
H9A	0.8880	0.8194	0.1136	0.021*
H9B	0.7344	0.6765	0.0848	0.021*
C10	0.9942 (2)	0.61698 (13)	0.19529 (8)	0.0177 (2)
H10A	1.0268	0.5071	0.1796	0.021*
H10B	1.1730	0.6511	0.2100	0.021*
C11	0.7643 (2)	0.63642 (13)	0.29187 (8)	0.0159 (2)
O12	0.55540 (18)	0.72858 (11)	0.28796 (7)	0.02341 (18)
O13	0.80467 (17)	0.55410 (10)	0.37393 (6)	0.01937 (17)
O14	0.26378 (17)	0.70791 (10)	0.47964 (6)	0.01973 (17)
H14A	0.3264	0.7271	0.4179	0.030*
H14B	0.0952	0.7007	0.4849	0.030*
O15	0.71999 (16)	0.60521 (10)	0.59458 (6)	0.01836 (17)
H15A	0.6207	0.6252	0.6514	0.028*
H15B	0.8596	0.5522	0.6092	0.028*

	U11	U22	U33	U12	U13	U23
Ni1	0.01095 (10)	0.01935 (11)	0.01075 (10)	0.00213 (7)	−0.00158 (7)	0.00208 (7)
N1	0.0229 (5)	0.0205 (5)	0.0145 (4)	−0.0001 (4)	−0.0011 (4)	−0.0011 (4)
C2	0.0191 (5)	0.0181 (5)	0.0127 (5)	−0.0037 (4)	−0.0019 (4)	−0.0001 (4)
C3	0.0223 (5)	0.0220 (6)	0.0178 (5)	0.0001 (4)	−0.0012 (4)	0.0002 (4)
C4	0.0277 (6)	0.0222 (6)	0.0259 (6)	0.0029 (5)	−0.0068 (5)	0.0018 (5)
C5	0.0399 (7)	0.0273 (6)	0.0199 (6)	0.0009 (5)	−0.0090 (5)	0.0055 (5)
C6	0.0377 (7)	0.0291 (6)	0.0135 (5)	0.0006 (5)	−0.0017 (5)	0.0019 (5)
O7	0.0259 (4)	0.0308 (5)	0.0188 (4)	0.0075 (4)	0.0012 (3)	−0.0025 (3)
S8	0.01735 (13)	0.02289 (15)	0.01281 (13)	0.00103 (10)	−0.00070 (10)	0.00202 (10)
C9	0.0165 (5)	0.0228 (5)	0.0121 (5)	−0.0006 (4)	−0.0004 (4)	0.0017 (4)
C10	0.0159 (5)	0.0229 (5)	0.0131 (5)	−0.0003 (4)	−0.0016 (4)	0.0021 (4)
C11	0.0147 (5)	0.0205 (5)	0.0127 (5)	−0.0024 (4)	−0.0027 (4)	0.0011 (4)
O12	0.0214 (4)	0.0286 (5)	0.0168 (4)	0.0067 (3)	−0.0004 (3)	0.0053 (3)
O13	0.0137 (4)	0.0298 (4)	0.0129 (4)	0.0020 (3)	−0.0015 (3)	0.0052 (3)
O14	0.0164 (4)	0.0241 (4)	0.0169 (4)	0.0030 (3)	−0.0013 (3)	0.0019 (3)
O15	0.0147 (4)	0.0256 (4)	0.0139 (4)	0.0030 (3)	−0.0024 (3)	−0.0009 (3)

Ni1—O13i	2.0488 (8)	C5—H5	0.9500
Ni1—O13	2.0488 (8)	C6—H6	0.9500
Ni1—O15i	2.0644 (8)	S8—C9	1.8165 (11)
Ni1—O15	2.0644 (8)	C9—C10	1.5216 (15)
Ni1—O14	2.0898 (8)	C9—H9A	0.9900
Ni1—O14i	2.0898 (8)	C9—H9B	0.9900
N1—O7	1.3154 (13)	C10—C11	1.5195 (15)
N1—C6	1.3579 (16)	C10—H10A	0.9900
N1—C2	1.3687 (14)	C10—H10B	0.9900
C2—C3	1.3889 (16)	C11—O12	1.2395 (14)
C2—S8	1.7405 (11)	C11—O13	1.2818 (13)
C3—C4	1.3823 (17)	O14—H14A	0.8142
C3—H3	0.9500	O14—H14B	0.8100
C4—C5	1.3877 (19)	O15—H15A	0.8216
C4—H4	0.9500	O15—H15B	0.8268
C5—C6	1.3685 (19)
O13i—Ni1—O13	180.0	C6—C5—H5	120.2
O13i—Ni1—O15i	88.53 (3)	C4—C5—H5	120.2
O13—Ni1—O15i	91.47 (3)	N1—C6—C5	120.67 (11)
O13i—Ni1—O15	91.47 (3)	N1—C6—H6	119.7
O13—Ni1—O15	88.53 (3)	C5—C6—H6	119.7
O15i—Ni1—O15	180.0	C2—S8—C9	100.23 (5)
O13i—Ni1—O14	88.50 (3)	C10—C9—S8	108.10 (8)
O13—Ni1—O14	91.50 (3)	C10—C9—H9A	110.1
O15i—Ni1—O14	90.66 (3)	S8—C9—H9A	110.1
O15—Ni1—O14	89.34 (3)	C10—C9—H9B	110.1
O13i—Ni1—O14i	91.50 (3)	S8—C9—H9B	110.1
O13—Ni1—O14i	88.50 (3)	H9A—C9—H9B	108.4
O15i—Ni1—O14i	89.34 (3)	C11—C10—C9	111.71 (9)
O15—Ni1—O14i	90.66 (3)	C11—C10—H10A	109.3
O14—Ni1—O14i	180.0	C9—C10—H10A	109.3
O7—N1—C6	121.11 (10)	C11—C10—H10B	109.3
O7—N1—C2	117.75 (10)	C9—C10—H10B	109.3
C6—N1—C2	121.15 (10)	H10A—C10—H10B	107.9
N1—C2—C3	118.82 (10)	O12—C11—O13	124.27 (10)
N1—C2—S8	112.99 (8)	O12—C11—C10	119.85 (10)
C3—C2—S8	128.19 (9)	O13—C11—C10	115.87 (9)
C4—C3—C2	120.43 (11)	C11—O13—Ni1	126.08 (7)
C4—C3—H3	119.8	Ni1—O14—H14A	98.9
C2—C3—H3	119.8	Ni1—O14—H14B	114.4
C3—C4—C5	119.25 (12)	H14A—O14—H14B	107.5
C3—C4—H4	120.4	Ni1—O15—H15A	111.7
C5—C4—H4	120.4	Ni1—O15—H15B	113.8
C6—C5—C4	119.69 (12)	H15A—O15—H15B	105.3
O7—N1—C2—C3	−179.71 (10)	N1—C2—S8—C9	−171.71 (9)
C6—N1—C2—C3	0.08 (17)	C3—C2—S8—C9	7.83 (12)
O7—N1—C2—S8	−0.12 (14)	C2—S8—C9—C10	−178.14 (8)
C6—N1—C2—S8	179.66 (10)	S8—C9—C10—C11	−178.64 (8)
N1—C2—C3—C4	−0.39 (18)	C9—C10—C11—O12	−5.56 (15)
S8—C2—C3—C4	−179.90 (10)	C9—C10—C11—O13	175.00 (10)
C2—C3—C4—C5	0.4 (2)	O12—C11—O13—Ni1	20.56 (17)
C3—C4—C5—C6	−0.1 (2)	C10—C11—O13—Ni1	−160.03 (7)
O7—N1—C6—C5	179.99 (12)	O15—Ni1—O13—C11	−120.55 (9)
C2—N1—C6—C5	0.2 (2)	O14—Ni1—O13—C11	−31.25 (10)
C4—C5—C6—N1	−0.2 (2)

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···O15ii	0.81	2.27	2.9517 (12)	142
O14—H14B···O13ii	0.81	2.64	3.2316 (12)	131
O15—H15A···O7iii	0.82	1.83	2.6469 (12)	172
O15—H15B···O13iv	0.83	1.83	2.6570 (11)	172
C4—H4···O12v	0.95	2.48	3.2044 (17)	133
C6—H6···O14vi	0.95	2.46	3.2515 (16)	140
C10—H10B···O12vii	0.99	2.42	3.3910 (14)	167

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)

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⋯O12iv	0.95	2.48	3.2044 (17)	133
C6—H6⋯O14v	0.95	2.46	3.2515 (16)	140
C10—H10B⋯O12vi	0.99	2.42	3.3910 (14)	167

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