Tetra-quabis(5-fluoro-saccharinato)nickel(II).

In the centrosymmetric title complex, [Ni(C(7)H(3)FNO(3)S)(2)(H(2)O)(4)], the Ni(II) atom exhibits a slightly distorted trans-NiN(2)O(4) octa-hedral coordination. The nitro-gen donors are provided by two 5-fluoro-saccharinate ligands and the oxygen donors are provided by four water mol-ecules. The crystal structure features O-H⋯O and bifurcated O-H⋯(F,O) hydrogen bonds, the latter involving the F atom of the 5-fluoro-saccharinate ligand.

Related literature

For a related structure; see: Haider et al. (1983 ▶). For background, see: Falvello et al. (2001 ▶); Khalil et al. (2005 ▶); Plenio (1997 ▶).

Experimental

Crystal data

[Ni(C7H3FNO3S)2(H2O)4]

M = 531.10

Triclinic,

a = 6.9649 (3) Å

b = 8.0484 (3) Å

c = 9.5877 (4) Å

α = 101.780 (1)°

β = 105.983 (1)°

γ = 110.973 (1)°

V = 454.18 (3) Å3

Z = 1

Mo Kα radiation

μ = 1.38 mm−1

T = 150 K

0.22 × 0.18 × 0.08 mm

Data collection

Bruker SMART APEX CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2003 ▶) T min = 0.887, T max = 1.000 (expected range = 0.794–0.895)

6861 measured reflections

1858 independent reflections

1769 reflections with I > 2σ(I)

R int = 0.022

Refinement

R[F 2 > 2σ(F 2)] = 0.024

wR(F 2) = 0.065

S = 1.06

1858 reflections

161 parameters

Only H-atom displacement parameters refined

Δρmax = 0.38 e Å−3

Δρmin = −0.37 e Å−3

Data collection: SMART (Bruker, 2003 ▶); cell refinement: SAINT-Plus (Bruker, 2003 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg, 2005 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809007053/hb2907sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809007053/hb2907Isup2.hkl

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

[Ni(C7H3FNO3S)2(H2O)4]	Z = 1
Mr = 531.10	F(000) = 270
Triclinic, P1	Dx = 1.942 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.9649 (3) Å	Cell parameters from 4507 reflections
b = 8.0484 (3) Å	θ = 2.4–26.4°
c = 9.5877 (4) Å	µ = 1.38 mm−1
α = 101.780 (1)°	T = 150 K
β = 105.983 (1)°	Block, light blue
γ = 110.973 (1)°	0.22 × 0.18 × 0.08 mm
V = 454.18 (3) Å3

Bruker SMART APEX CCD diffractometer	1858 independent reflections
Radiation source: fine-focus sealed tube	1769 reflections with I > 2σ(I)
graphite	Rint = 0.022
ω scans	θmax = 26.4°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2003)	h = −8→8
Tmin = 0.887, Tmax = 1.000	k = −10→10
6861 measured reflections	l = −11→11

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: mixed
wR(F2) = 0.065	Only H-atom displacement parameters refined
S = 1.06	w = 1/[σ2(Fo2) + (0.0376P)2 + 0.2342P] where P = (Fo2 + 2Fc2)/3
1858 reflections	(Δ/σ)max < 0.001
161 parameters	Δρmax = 0.38 e Å−3
0 restraints	Δρmin = −0.37 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	0.01450 (11)
S1	−0.01342 (6)	0.32955 (6)	0.24583 (5)	0.01495 (12)
C1	0.2752 (3)	0.2997 (2)	0.1523 (2)	0.0176 (4)
C2	0.0749 (3)	0.2377 (2)	0.0098 (2)	0.0164 (3)
C3	0.0542 (3)	0.1736 (2)	−0.1416 (2)	0.0179 (3)
H3	0.1724	0.1621	−0.1670	0.020 (5)*
C4	−0.1482 (3)	0.1274 (2)	−0.2531 (2)	0.0179 (3)
C5	−0.3263 (3)	0.1414 (3)	−0.2223 (2)	0.0217 (4)
H5	−0.4613	0.1090	−0.3041	0.036 (6)*
C6	−0.3043 (3)	0.2036 (3)	−0.0695 (2)	0.0209 (4)
H6	−0.4232	0.2132	−0.0438	0.026 (6)*
C7	−0.1013 (3)	0.2507 (2)	0.04337 (19)	0.0169 (3)
F1	−0.17280 (17)	0.06728 (16)	−0.40248 (12)	0.0230 (2)
N1	0.2420 (2)	0.3605 (2)	0.28345 (17)	0.0172 (3)
O1	0.4490 (2)	0.2954 (2)	0.15047 (15)	0.0258 (3)
O2	−0.1302 (2)	0.18308 (18)	0.29833 (15)	0.0210 (3)
O3	−0.01877 (19)	0.50819 (17)	0.30498 (14)	0.0193 (3)
O4	0.2988 (2)	0.3398 (2)	0.59836 (16)	0.0197 (3)
H4A	0.190 (5)	0.249 (4)	0.535 (4)	0.048 (8)*
H4B	0.254 (5)	0.396 (4)	0.646 (3)	0.043 (8)*
O5	0.4047 (2)	0.71025 (18)	0.54925 (17)	0.0187 (3)
H5A	0.284 (5)	0.685 (4)	0.490 (3)	0.046 (8)*
H5B	0.412 (4)	0.742 (4)	0.637 (3)	0.039 (7)*

	U11	U22	U33	U12	U13	U23
Ni1	0.01254 (16)	0.01878 (18)	0.01260 (17)	0.00792 (13)	0.00498 (12)	0.00392 (12)
S1	0.0128 (2)	0.0187 (2)	0.0134 (2)	0.00758 (17)	0.00549 (16)	0.00357 (17)
C1	0.0179 (8)	0.0214 (9)	0.0152 (8)	0.0101 (7)	0.0070 (7)	0.0056 (7)
C2	0.0156 (8)	0.0175 (8)	0.0163 (9)	0.0077 (7)	0.0058 (7)	0.0058 (7)
C3	0.0183 (8)	0.0192 (8)	0.0183 (9)	0.0092 (7)	0.0086 (7)	0.0066 (7)
C4	0.0228 (8)	0.0174 (8)	0.0126 (8)	0.0079 (7)	0.0073 (7)	0.0043 (7)
C5	0.0173 (8)	0.0242 (9)	0.0189 (9)	0.0081 (7)	0.0031 (7)	0.0052 (7)
C6	0.0168 (8)	0.0261 (9)	0.0190 (9)	0.0096 (7)	0.0070 (7)	0.0052 (7)
C7	0.0180 (8)	0.0181 (8)	0.0135 (8)	0.0079 (7)	0.0063 (7)	0.0030 (7)
F1	0.0246 (5)	0.0294 (6)	0.0125 (5)	0.0113 (5)	0.0064 (4)	0.0040 (4)
N1	0.0129 (6)	0.0241 (8)	0.0148 (7)	0.0100 (6)	0.0050 (6)	0.0040 (6)
O1	0.0188 (6)	0.0437 (8)	0.0177 (7)	0.0188 (6)	0.0073 (5)	0.0061 (6)
O2	0.0216 (6)	0.0228 (7)	0.0200 (7)	0.0090 (5)	0.0109 (5)	0.0073 (5)
O3	0.0170 (6)	0.0202 (6)	0.0196 (6)	0.0096 (5)	0.0062 (5)	0.0030 (5)
O4	0.0184 (6)	0.0213 (7)	0.0188 (7)	0.0082 (6)	0.0087 (6)	0.0044 (6)
O5	0.0170 (6)	0.0229 (7)	0.0163 (7)	0.0105 (5)	0.0060 (5)	0.0042 (5)

Ni1—O5i	2.0440 (13)	C2—C3	1.385 (2)
Ni1—O5	2.0440 (13)	C3—C4	1.379 (2)
Ni1—N1	2.0856 (14)	C3—H3	0.9500
Ni1—N1i	2.0856 (14)	C4—F1	1.355 (2)
Ni1—O4	2.1084 (13)	C4—C5	1.388 (2)
Ni1—O4i	2.1084 (13)	C5—C6	1.394 (3)
S1—O2	1.4443 (13)	C5—H5	0.9500
S1—O3	1.4515 (13)	C6—C7	1.385 (2)
S1—N1	1.6277 (14)	C6—H6	0.9500
S1—C7	1.7635 (17)	O4—H4A	0.81 (3)
C1—O1	1.228 (2)	O4—H4B	0.78 (3)
C1—N1	1.366 (2)	O5—H5A	0.80 (3)
C1—C2	1.495 (2)	O5—H5B	0.81 (3)
C2—C7	1.385 (2)
O5i—Ni1—O5	180.0	C3—C2—C1	127.30 (15)
O5i—Ni1—N1	87.50 (6)	C4—C3—C2	116.09 (15)
O5—Ni1—N1	92.50 (6)	C4—C3—H3	122.0
O5i—Ni1—N1i	92.50 (6)	C2—C3—H3	122.0
O5—Ni1—N1i	87.50 (6)	F1—C4—C3	117.60 (15)
N1—Ni1—N1i	180.0	F1—C4—C5	118.11 (16)
O5i—Ni1—O4	88.53 (5)	C3—C4—C5	124.28 (17)
O5—Ni1—O4	91.47 (5)	C4—C5—C6	119.03 (16)
N1—Ni1—O4	90.65 (6)	C4—C5—H5	120.5
N1i—Ni1—O4	89.35 (6)	C6—C5—H5	120.5
O5i—Ni1—O4i	91.47 (5)	C7—C6—C5	117.06 (16)
O5—Ni1—O4i	88.53 (5)	C7—C6—H6	121.5
N1—Ni1—O4i	89.35 (6)	C5—C6—H6	121.5
N1i—Ni1—O4i	90.65 (6)	C2—C7—C6	122.86 (16)
O4—Ni1—O4i	180.0	C2—C7—S1	107.03 (13)
O2—S1—O3	114.08 (7)	C6—C7—S1	130.10 (13)
O2—S1—N1	110.96 (8)	C1—N1—S1	111.66 (12)
O3—S1—N1	110.42 (7)	C1—N1—Ni1	122.66 (11)
O2—S1—C7	111.32 (8)	S1—N1—Ni1	125.40 (8)
O3—S1—C7	112.14 (8)	Ni1—O4—H4A	113 (2)
N1—S1—C7	96.63 (8)	Ni1—O4—H4B	113 (2)
O1—C1—N1	124.25 (16)	H4A—O4—H4B	106 (3)
O1—C1—C2	123.43 (16)	Ni1—O5—H5A	113 (2)
N1—C1—C2	112.32 (14)	Ni1—O5—H5B	113.5 (19)
C7—C2—C3	120.66 (16)	H5A—O5—H5B	110 (3)
C7—C2—C1	112.04 (15)
O1—C1—C2—C7	177.99 (17)	O3—S1—C7—C6	−61.72 (19)
N1—C1—C2—C7	−1.9 (2)	N1—S1—C7—C6	−176.96 (18)
O1—C1—C2—C3	−2.1 (3)	O1—C1—N1—S1	−174.70 (15)
N1—C1—C2—C3	178.04 (16)	C2—C1—N1—S1	5.15 (19)
C7—C2—C3—C4	0.8 (3)	O1—C1—N1—Ni1	11.1 (3)
C1—C2—C3—C4	−179.07 (16)	C2—C1—N1—Ni1	−169.10 (11)
C2—C3—C4—F1	178.87 (14)	O2—S1—N1—C1	110.32 (13)
C2—C3—C4—C5	0.0 (3)	O3—S1—N1—C1	−122.18 (13)
F1—C4—C5—C6	−179.76 (16)	C7—S1—N1—C1	−5.56 (14)
C3—C4—C5—C6	−0.9 (3)	O2—S1—N1—Ni1	−75.62 (11)
C4—C5—C6—C7	0.9 (3)	O3—S1—N1—Ni1	51.87 (12)
C3—C2—C7—C6	−0.7 (3)	C7—S1—N1—Ni1	168.50 (10)
C1—C2—C7—C6	179.18 (16)	O5i—Ni1—N1—C1	−48.82 (14)
C3—C2—C7—S1	178.11 (14)	O5—Ni1—N1—C1	131.18 (14)
C1—C2—C7—S1	−1.98 (18)	O4—Ni1—N1—C1	−137.32 (14)
C5—C6—C7—C2	−0.2 (3)	O4i—Ni1—N1—C1	42.68 (14)
C5—C6—C7—S1	−178.74 (14)	O5i—Ni1—N1—S1	137.74 (10)
O2—S1—C7—C2	−111.27 (13)	O5—Ni1—N1—S1	−42.26 (10)
O3—S1—C7—C2	119.56 (12)	O4—Ni1—N1—S1	49.24 (10)
N1—S1—C7—C2	4.32 (14)	O4i—Ni1—N1—S1	−130.76 (10)
O2—S1—C7—C6	67.46 (19)

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4A···O2	0.81 (3)	2.51 (3)	3.1436 (19)	137 (3)
O4—H4A···F1ii	0.81 (3)	2.54 (3)	3.0910 (19)	127 (3)
O4—H4B···O3iii	0.78 (3)	2.17 (3)	2.8985 (18)	158 (3)
O5—H5A···O3	0.80 (3)	2.10 (3)	2.8346 (18)	155 (3)
O5—H5A···F1iv	0.80 (3)	2.59 (3)	3.1050 (17)	124 (2)
O5—H5B···O1i	0.81 (3)	2.13 (3)	2.793 (2)	139 (2)
O5—H5B···O2iii	0.81 (3)	2.44 (3)	2.9541 (18)	122 (2)

Table 1

Selected bond lengths (Å)

Ni1—O5	2.0440 (13)
Ni1—N1	2.0856 (14)
Ni1—O4	2.1084 (13)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O4—H4A⋯O2	0.81 (3)	2.51 (3)	3.1436 (19)	137 (3)
O4—H4A⋯F1i	0.81 (3)	2.54 (3)	3.0910 (19)	127 (3)
O4—H4B⋯O3ii	0.78 (3)	2.17 (3)	2.8985 (18)	158 (3)
O5—H5A⋯O3	0.80 (3)	2.10 (3)	2.8346 (18)	155 (3)
O5—H5A⋯F1iii	0.80 (3)	2.59 (3)	3.1050 (17)	124 (2)
O5—H5B⋯O1iv	0.81 (3)	2.13 (3)	2.793 (2)	139 (2)
O5—H5B⋯O2ii	0.81 (3)	2.44 (3)	2.9541 (18)	122 (2)

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