Di-aqua-bis-[N-(2-fluoro-benz-yl)-N-nitroso-hydroxy-laminato-κ(2) O,O']nickel(II).

In the centrosymmetric title compound, [Ni(C7H6FN2O2)2(H2O)2], the Ni(II) cation is in a slightly distorted octa-hedral environment and is surrounded by four O atoms from the N-O groups of the organic ligands [Ni-O = 2.0179 (13) and 2.0283 (12) Å], and two water mol-ecules [Ni-O = 2.0967 (14) Å]. The N-(2-fluoro-benz-yl)-N-nitroso-hydroxy-laminate monoanions act as bidentate chelating ligands. In the crystal, the Ni cations in the columns are shifted in such a way that the coordinated water mol-ecules are involved in the formation of hydrogen bonds with the O atoms of the organic species of neighbouring mol-ecules. Thus, a two-dimensional network parallel to (100) is built up by hydrogen-bonded molecules.

Related literature

For the synthesis of the potassium N-(2-fluoro­benz­yl)-N-nitroso­hydroxy­laminate salt, see: Zyuzin et al. (1997 ▶) and of the Ni complex of N-(2-fluoro­benz­yl)-N-nitroso­hydroxy­laminate, see: Kovalchukova et al. (2013 ▶). For the structures of some 3d-metal complexes with N-nitroso­hydroxyl­amine deriv­atives, see: Deák et al. (1998 ▶); Okabe & Tamaki (1995 ▶); Tamaki & Okabe (1996 ▶, 1998 ▶). For the synthesis, properties and applications of other metal nitroso­hydroxy­laminates, see: Okabe et al. (1995 ▶); Abraham et al. (1987 ▶); Venter et al. (2009 ▶); Popov & Wendlandt (1954 ▶); Lundell & Knowles (1920 ▶); Buscarons & Canela (1974 ▶); Oztekin & Erim (2000 ▶); Yi et al. (1995 ▶); McGill et al. (2000 ▶); Shiino et al. (2001 ▶).

Experimental

Crystal data

[Ni(C7H6FN2O2)2(H2O)2]

M = 433.02

Monoclinic,

a = 15.411 (3) Å

b = 7.235 (1) Å

c = 7.604 (1) Å

β = 91.65 (3)°

V = 847.5 (3) Å3

Z = 2

Mo Kα radiation

μ = 1.21 mm−1

T = 293 K

0.75 × 0.20 × 0.05 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: part of the refinement model (ΔF) (Walker & Stuart, 1983 ▶) T min = 0.427, T max = 0.809

1703 measured reflections

1571 independent reflections

1181 reflections with I > 2σ(I)

R int = 0.022

3 standard reflections every 60 min intensity decay: 0.0%

Refinement

R[F 2 > 2σ(F 2)] = 0.022

wR(F 2) = 0.066

S = 1.01

1571 reflections

132 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.31 e Å−3

Δρmin = −0.32 e Å−3

Data collection: CAD-4-PC (Enraf–Nonius, 1993 ▶); cell refinement: CAD-4-PC; data reduction: CAD-4-PC; 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: CIFTAB97 (Sheldrick, 2008 ▶) and SHELX97.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536814002876/bv2230sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814002876/bv2230Isup2.hkl

CCDC reference: 985943

Additional supporting information: crystallographic information; 3D view; checkCIF report

[Ni(C7H6FN2O2)2(H2O)2]	F(000) = 444
Mr = 433.02	Dx = 1.697 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 15.411 (3) Å	Cell parameters from 24 reflections
b = 7.235 (1) Å	θ = 10.9–12.5°
c = 7.604 (1) Å	µ = 1.21 mm−1
β = 91.65 (3)°	T = 293 K
V = 847.5 (3) Å3	Plate, green
Z = 2	0.75 × 0.20 × 0.05 mm

Enraf–Nonius CAD-4 diffractometer	1181 reflections with I > 2σ(I)
Radiation source: fine-focus tube	Rint = 0.022
β-filter monochromator	θmax = 25.5°, θmin = 2.6°
ω/2θ scans	h = −18→18
Absorption correction: part of the refinement model (ΔF) (Walker & Stuart, 1983)	k = 0→8
Tmin = 0.427, Tmax = 0.809	l = 0→9
1703 measured reflections	3 standard reflections every 60 min
1571 independent reflections	intensity decay: 0.0%

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)] = 0.022	Hydrogen site location: difference Fourier map
wR(F2) = 0.066	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ2(Fo2) + (0.0471P)2] where P = (Fo2 + 2Fc2)/3
1571 reflections	(Δ/σ)max < 0.001
132 parameters	Δρmax = 0.31 e Å−3
2 restraints	Δρmin = −0.32 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	0.02414 (12)
F1	0.12983 (10)	0.46369 (18)	0.3199 (2)	0.0610 (4)
O1	0.39701 (8)	0.63578 (16)	0.39297 (15)	0.0292 (3)
O2	0.41642 (8)	0.28946 (16)	0.44659 (16)	0.0312 (3)
N1	0.34766 (9)	0.51068 (19)	0.31185 (19)	0.0278 (3)
N2	0.35419 (10)	0.3370 (2)	0.3362 (2)	0.0317 (3)
C1	0.14337 (13)	0.6479 (3)	0.3049 (3)	0.0386 (4)
C2	0.22021 (12)	0.7072 (3)	0.2360 (2)	0.0329 (4)
C3	0.23158 (14)	0.8967 (3)	0.2205 (3)	0.0406 (5)
H3	0.2824	0.9423	0.1738	0.049*
C4	0.16858 (17)	1.0184 (3)	0.2733 (3)	0.0519 (6)
H4	0.1773	1.1451	0.2629	0.062*
C5	0.09283 (16)	0.9527 (3)	0.3412 (3)	0.0531 (6)
H5	0.0504	1.0354	0.3760	0.064*
C6	0.07923 (13)	0.7649 (3)	0.3581 (3)	0.0477 (5)
H6	0.0282	0.7193	0.4041	0.057*
C7	0.28684 (13)	0.5742 (3)	0.1721 (2)	0.0369 (4)
H71	0.2575	0.4679	0.1206	0.044*
H72	0.3194	0.6333	0.0805	0.044*
O3	0.45896 (10)	0.53062 (17)	0.75889 (18)	0.0371 (3)
H31	0.4344 (17)	0.628 (3)	0.790 (4)	0.075 (9)*
H32	0.4418 (15)	0.443 (2)	0.821 (3)	0.052 (7)*

	U11	U22	U33	U12	U13	U23
Ni1	0.02426 (18)	0.02405 (17)	0.02409 (17)	0.00166 (12)	0.00050 (11)	0.00039 (11)
F1	0.0577 (8)	0.0447 (7)	0.0812 (10)	−0.0079 (6)	0.0135 (7)	−0.0001 (6)
O1	0.0292 (6)	0.0261 (5)	0.0321 (6)	0.0014 (5)	−0.0027 (5)	−0.0010 (5)
O2	0.0330 (7)	0.0271 (6)	0.0335 (6)	−0.0003 (5)	−0.0004 (5)	0.0022 (5)
N1	0.0243 (7)	0.0317 (7)	0.0274 (7)	0.0030 (6)	−0.0003 (6)	−0.0027 (6)
N2	0.0304 (8)	0.0317 (8)	0.0331 (7)	0.0006 (6)	0.0021 (6)	−0.0030 (6)
C1	0.0366 (11)	0.0405 (10)	0.0382 (10)	0.0008 (8)	−0.0049 (8)	−0.0023 (8)
C2	0.0286 (9)	0.0419 (10)	0.0279 (9)	0.0051 (7)	−0.0059 (7)	−0.0005 (7)
C3	0.0381 (11)	0.0441 (11)	0.0394 (10)	0.0001 (8)	−0.0046 (9)	0.0047 (8)
C4	0.0595 (14)	0.0403 (11)	0.0553 (13)	0.0083 (10)	−0.0067 (11)	0.0006 (9)
C5	0.0494 (13)	0.0590 (14)	0.0504 (13)	0.0228 (11)	−0.0050 (10)	−0.0083 (10)
C6	0.0317 (11)	0.0679 (15)	0.0434 (11)	0.0052 (10)	0.0013 (9)	−0.0062 (10)
C7	0.0351 (10)	0.0484 (10)	0.0269 (9)	0.0077 (9)	−0.0029 (8)	−0.0001 (8)
O3	0.0518 (8)	0.0300 (7)	0.0303 (6)	0.0022 (6)	0.0127 (6)	0.0008 (5)

Ni1—O1i	2.0179 (13)	C2—C3	1.388 (3)
Ni1—O1	2.0179 (13)	C2—C7	1.498 (3)
Ni1—O2	2.0283 (12)	C3—C4	1.379 (3)
Ni1—O2i	2.0283 (12)	C3—H3	0.9300
Ni1—O3	2.0967 (14)	C4—C5	1.375 (4)
Ni1—O3i	2.0967 (14)	C4—H4	0.9300
F1—C1	1.354 (2)	C5—C6	1.381 (3)
O1—N1	1.3233 (19)	C5—H5	0.9300
O2—N2	1.302 (2)	C6—H6	0.9300
N1—N2	1.274 (2)	C7—H71	0.9700
N1—C7	1.470 (2)	C7—H72	0.9700
C1—C6	1.371 (3)	O3—H31	0.838 (10)
C1—C2	1.377 (3)	O3—H32	0.837 (10)
O1i—Ni1—O1	180.0	C1—C2—C3	116.90 (18)
O1i—Ni1—O2	101.70 (5)	C1—C2—C7	121.86 (17)
O1—Ni1—O2	78.30 (5)	C3—C2—C7	121.17 (18)
O1i—Ni1—O2i	78.30 (5)	C4—C3—C2	121.0 (2)
O1—Ni1—O2i	101.70 (5)	C4—C3—H3	119.5
O2—Ni1—O2i	180.0	C2—C3—H3	119.5
O1i—Ni1—O3	85.86 (6)	C5—C4—C3	120.1 (2)
O1—Ni1—O3	94.14 (6)	C5—C4—H4	120.0
O2—Ni1—O3	93.46 (6)	C3—C4—H4	120.0
O2i—Ni1—O3	86.54 (6)	C4—C5—C6	120.5 (2)
O1i—Ni1—O3i	94.14 (6)	C4—C5—H5	119.7
O1—Ni1—O3i	85.86 (6)	C6—C5—H5	119.7
O2—Ni1—O3i	86.54 (6)	C1—C6—C5	117.8 (2)
O2i—Ni1—O3i	93.46 (6)	C1—C6—H6	121.1
O3—Ni1—O3i	180.0	C5—C6—H6	121.1
N1—O1—Ni1	106.85 (9)	N1—C7—C2	113.27 (14)
N2—O2—Ni1	112.47 (10)	N1—C7—H71	108.9
N2—N1—O1	124.40 (14)	C2—C7—H71	108.9
N2—N1—C7	117.37 (14)	N1—C7—H72	108.9
O1—N1—C7	117.96 (14)	C2—C7—H72	108.9
N1—N2—O2	114.08 (14)	H71—C7—H72	107.7
F1—C1—C6	117.94 (19)	Ni1—O3—H31	120 (2)
F1—C1—C2	118.37 (17)	Ni1—O3—H32	124.0 (18)
C6—C1—C2	123.69 (19)	H31—O3—H32	109 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H31···O1ii	0.84 (1)	1.97 (1)	2.7987 (18)	169 (3)
O3—H32···O2iii	0.84 (1)	1.98 (1)	2.8078 (18)	170 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H31⋯O1i	0.84 (1)	1.97 (1)	2.7987 (18)	169 (3)
O3—H32⋯O2ii	0.84 (1)	1.98 (1)	2.8078 (18)	170 (2)

Symmetry codes: (i) ; (ii) .