Aqua-bis(2-amino-1,3-thia-zole-4-acetato-κO,N)nickel(II).

In the crystal structure of the title compound, [Ni(C(5)H(5)N(2)O(2)S)(2)(H(2)O)], the Ni(II) cation is located on a twofold rotation axis and chelated by two 2-amino-1,3-thia-zole-4-acetate (ata) anions in the basal coordination plane; a water mol-ecule located on the same twofold rotation axis completes the distorted square-pyramidal coordination geometry. Inter-molecular O-H⋯O and N-H⋯O hydrogen bonding, as well as π-π stacking between parallel thia-zole rings [centroid-centroid distance 3.531 (8) Å], helps to stabilize the crystal structure.

Related literature

For general background to the potential use of discrete and polymeric metal-organic complexes as functional materials in catalysis, mol­ecular recognition, separation and non-linear optics, see: Batten & Robson (1998 ▶); Fujita et al. (1994 ▶); Han et al. (2008 ▶); Wu et al. (2001 ▶).

Experimental

Crystal data

[Ni(C5H5N2O2S)2(H2O)]

M = 391.07

Monoclinic,

a = 12.0875 (12) Å

b = 9.1278 (9) Å

c = 12.7715 (12) Å

β = 95.1190 (10)°

V = 1403.5 (2) Å3

Z = 4

Mo Kα radiation

μ = 1.71 mm−1

T = 293 K

0.12 × 0.10 × 0.06 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.821, T max = 0.904

3487 measured reflections

1231 independent reflections

1119 reflections with I > 2σ(I)

R int = 0.014

Refinement

R[F 2 > 2σ(F 2)] = 0.024

wR(F 2) = 0.065

S = 1.01

1231 reflections

102 parameters

H-atom parameters constrained

Δρmax = 0.31 e Å−3

Δρmin = −0.29 e Å−3

Data collection: SMART (Bruker, 1997 ▶); cell refinement: SAINT (Bruker, 1997 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809017978/xu2518sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809017978/xu2518Isup2.hkl

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

[Ni(C5H5N2O2S)2(H2O)]	F(000) = 800
Mr = 391.07	Dx = 1.851 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 2106 reflections
a = 12.0875 (12) Å	θ = 2.8–25.0°
b = 9.1278 (9) Å	µ = 1.71 mm−1
c = 12.7715 (12) Å	T = 293 K
β = 95.119 (1)°	Prism, green
V = 1403.5 (2) Å3	0.12 × 0.10 × 0.06 mm
Z = 4

Bruker SMART CCD diffractometer	1231 independent reflections
Radiation source: fine-focus sealed tube	1119 reflections with I > 2σ(I)
graphite	Rint = 0.014
CCD Profile fitting scans	θmax = 25.0°, θmin = 2.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −14→14
Tmin = 0.821, Tmax = 0.904	k = −5→10
3487 measured reflections	l = −15→14

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)] = 0.024	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.065	H-atom parameters constrained
S = 1.01	w = 1/[σ2(Fo2) + (0.034P)2 + 2.301P] where P = (Fo2 + 2Fc2)/3
1231 reflections	(Δ/σ)max < 0.001
102 parameters	Δρmax = 0.31 e Å−3
0 restraints	Δρmin = −0.29 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	0.0000	0.69428 (4)	0.2500	0.02321 (14)
N1	0.10680 (18)	0.7919 (2)	0.49121 (17)	0.0423 (6)
H1A	0.1428	0.7976	0.4363	0.051*
H1B	0.1341	0.8297	0.5496	0.051*
N2	−0.04038 (14)	0.6630 (2)	0.40062 (14)	0.0264 (4)
O1	−0.16405 (12)	0.68137 (17)	0.20264 (12)	0.0314 (4)
O2	−0.33123 (12)	0.5835 (2)	0.19153 (12)	0.0369 (4)
O3	0.0000	0.9133 (2)	0.2500	0.0401 (6)
H3	0.0570	0.9433	0.2270	0.060*
C1	−0.23701 (16)	0.5998 (2)	0.23761 (16)	0.0254 (5)
C2	−0.20703 (19)	0.5149 (3)	0.33761 (18)	0.0336 (5)
H2A	−0.2751	0.4820	0.3650	0.040*
H2B	−0.1657	0.4283	0.3204	0.040*
C3	0.00918 (19)	0.7248 (3)	0.48595 (17)	0.0295 (5)
C4	−0.14006 (17)	0.5971 (2)	0.42235 (17)	0.0280 (5)
C5	−0.16604 (19)	0.6117 (3)	0.52138 (18)	0.0364 (6)
H5	−0.2299	0.5739	0.5468	0.044*
S1	−0.06560 (5)	0.71004 (8)	0.59589 (5)	0.03934 (19)

	U11	U22	U33	U12	U13	U23
Ni1	0.0186 (2)	0.0286 (2)	0.0224 (2)	0.000	0.00139 (15)	0.000
N1	0.0395 (12)	0.0586 (15)	0.0285 (11)	−0.0167 (11)	0.0017 (9)	−0.0117 (10)
N2	0.0241 (9)	0.0319 (10)	0.0229 (9)	−0.0007 (8)	0.0009 (7)	−0.0001 (8)
O1	0.0225 (8)	0.0422 (9)	0.0291 (9)	−0.0047 (7)	0.0005 (6)	0.0090 (7)
O2	0.0217 (8)	0.0551 (11)	0.0327 (9)	−0.0077 (7)	−0.0033 (6)	0.0127 (8)
O3	0.0262 (12)	0.0300 (12)	0.0666 (17)	0.000	0.0190 (12)	0.000
C1	0.0217 (11)	0.0292 (11)	0.0252 (11)	0.0004 (9)	0.0016 (9)	−0.0006 (9)
C2	0.0290 (11)	0.0352 (13)	0.0354 (13)	−0.0065 (10)	−0.0038 (10)	0.0099 (11)
C3	0.0294 (12)	0.0343 (13)	0.0246 (12)	0.0031 (10)	0.0014 (9)	−0.0006 (10)
C4	0.0239 (10)	0.0314 (12)	0.0281 (12)	0.0023 (9)	−0.0004 (9)	0.0071 (10)
C5	0.0278 (12)	0.0504 (15)	0.0311 (13)	0.0004 (11)	0.0039 (10)	0.0096 (12)
S1	0.0384 (4)	0.0570 (4)	0.0230 (3)	0.0039 (3)	0.0044 (3)	−0.0030 (3)

Ni1—O1	2.0243 (15)	O2—C1	1.243 (3)
Ni1—O1i	2.0243 (15)	O3—H3	0.8200
Ni1—O3	1.999 (2)	C1—C2	1.510 (3)
Ni1—N2	2.0465 (18)	C2—C4	1.494 (3)
Ni1—N2i	2.0465 (18)	C2—H2A	0.9700
N1—C3	1.326 (3)	C2—H2B	0.9700
N1—H1A	0.8600	C3—S1	1.742 (2)
N1—H1B	0.8600	C4—C5	1.337 (3)
N2—C3	1.322 (3)	C5—S1	1.726 (3)
N2—C4	1.397 (3)	C5—H5	0.9300
O1—C1	1.266 (3)
O3—Ni1—O1	93.34 (5)	O2—C1—C2	118.64 (19)
O3—Ni1—O1i	93.34 (5)	O1—C1—C2	118.57 (18)
O1—Ni1—O1i	173.33 (9)	C4—C2—C1	115.36 (19)
O3—Ni1—N2	98.02 (5)	C4—C2—H2A	108.4
O1—Ni1—N2	87.90 (7)	C1—C2—H2A	108.4
O1i—Ni1—N2	91.17 (7)	C4—C2—H2B	108.4
O3—Ni1—N2i	98.02 (5)	C1—C2—H2B	108.4
O1—Ni1—N2i	91.17 (7)	H2A—C2—H2B	107.5
O1i—Ni1—N2i	87.90 (7)	N2—C3—N1	125.1 (2)
N2—Ni1—N2i	163.96 (11)	N2—C3—S1	113.70 (17)
C3—N1—H1A	120.0	N1—C3—S1	121.23 (17)
C3—N1—H1B	120.0	C5—C4—N2	115.1 (2)
H1A—N1—H1B	120.0	C5—C4—C2	125.3 (2)
C3—N2—C4	110.83 (19)	N2—C4—C2	119.58 (19)
C3—N2—Ni1	125.93 (16)	C4—C5—S1	111.14 (18)
C4—N2—Ni1	121.96 (14)	C4—C5—H5	124.4
C1—O1—Ni1	128.58 (14)	S1—C5—H5	124.4
Ni1—O3—H3	109.5	C5—S1—C3	89.19 (11)
O2—C1—O1	122.8 (2)
O3—Ni1—N2—C3	−50.65 (19)	C4—N2—C3—N1	177.7 (2)
O1—Ni1—N2—C3	−143.73 (19)	Ni1—N2—C3—N1	−15.1 (3)
O1i—Ni1—N2—C3	42.88 (19)	C4—N2—C3—S1	−1.8 (2)
N2i—Ni1—N2—C3	129.35 (19)	Ni1—N2—C3—S1	165.31 (11)
O3—Ni1—N2—C4	115.15 (16)	C3—N2—C4—C5	1.4 (3)
O1—Ni1—N2—C4	22.08 (17)	Ni1—N2—C4—C5	−166.37 (17)
O1i—Ni1—N2—C4	−151.32 (17)	C3—N2—C4—C2	−177.3 (2)
N2i—Ni1—N2—C4	−64.85 (16)	Ni1—N2—C4—C2	15.0 (3)
O3—Ni1—O1—C1	−135.01 (18)	C1—C2—C4—C5	126.8 (3)
N2—Ni1—O1—C1	−37.09 (19)	C1—C2—C4—N2	−54.7 (3)
N2i—Ni1—O1—C1	126.88 (19)	N2—C4—C5—S1	−0.3 (3)
Ni1—O1—C1—O2	−167.76 (16)	C2—C4—C5—S1	178.27 (18)
Ni1—O1—C1—C2	10.2 (3)	C4—C5—S1—C3	−0.6 (2)
O2—C1—C2—C4	−140.5 (2)	N2—C3—S1—C5	1.44 (19)
O1—C1—C2—C4	41.5 (3)	N1—C3—S1—C5	−178.2 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1i	0.86	2.10	2.816 (3)	140
N1—H1B···O2ii	0.86	1.99	2.839 (3)	170
O3—H3···O2iii	0.82	1.94	2.7211 (19)	158

Table 1

Selected bond lengths (Å)

Ni1—O1	2.0243 (15)
Ni1—O3	1.999 (2)
Ni1—N2	2.0465 (18)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O1i	0.86	2.10	2.816 (3)	140
N1—H1B⋯O2ii	0.86	1.99	2.839 (3)	170
O3—H3⋯O2iii	0.82	1.94	2.7211 (19)	158

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