trans-Diaqua-bis-(dl-valinato-κN,O)nickel(II).

In the title complex, [Ni(C(5)H(9)NO(2))(2)(H(2)O)(2)], the Ni(II) atom, located on a centre of inversion, is trans-coordinated by two O atoms and two N atoms from d-bidentate valine and l-bidentate valine ligands and two water O atoms in an octa-hedral geometry. In the crystal, the discrete mononuclear units are linked into a three-dimensional network via O-H⋯O and N-H⋯O hydrogen bonds. C-H⋯O inter-actions are also observed.

Related literature

For amino ­acids as ligands, see: Loo et al. (2005 ▶); Patrick et al. (2003 ▶). For valine, see: Ooiwa et al. (1995 ▶). For related complexes, see: Menabue et al. (1998 ▶)

Experimental

Crystal data

[Ni(C5H9NO2)2(H2O)2]

M = 325.01

Monoclinic,

a = 24.8881 (2) Å

b = 5.8701 (3) Å

c = 10.0789 (2) Å

β = 90.442 (3)°

V = 1472.44 (8) Å3

Z = 4

Mo Kα radiation

μ = 1.34 mm−1

T = 293 K

0.20 × 0.15 × 0.10 mm

Data collection

Nonius Mach3 KappaCCD diffractometer

2024 measured reflections

1960 independent reflections

1053 reflections with I > 2σ(I)

R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.053

wR(F 2) = 0.151

S = 1.03

1960 reflections

94 parameters

1 restraint

H-atom parameters not refined

Δρmax = 0.48 e Å−3

Δρmin = −1.26 e Å−3

Data collection: KappaCCD Server Software (Nonius, 1998 ▶); cell refinement: DENZO and SCALEPACK (Otwinowski & Minor, 1997 ▶); data reduction: DENZO and SCALEPACK; program(s) used to solve structure: SIR2004 (Burla et al., 2005 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811031072/ds2128sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811031072/ds2128Isup2.hkl

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

[Ni(C5H9NO2)2(H2O)2]	F(000) = 688
Mr = 325.01	Dx = 1.466 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 1960 reflections
a = 24.8881 (2) Å	θ = 3.3–29.1°
b = 5.8701 (3) Å	µ = 1.34 mm−1
c = 10.0789 (2) Å	T = 293 K
β = 90.442 (3)°	Placket, blue
V = 1472.44 (8) Å3	0.20 × 0.15 × 0.10 mm
Z = 4

Nonius Mach3 KappaCCD diffractometer	1053 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.023
graphite	θmax = 29.2°, θmin = 3.3°
φ and ω scans	h = −31→16
2024 measured reflections	k = −4→7
1960 independent reflections	l = −13→10

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)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.151	H-atom parameters not refined
S = 1.03	w = 1/[σ2(Fo2) + (0.1031P)2] where P = (Fo2 + 2Fc2)/3
1960 reflections	(Δ/σ)max < 0.001
94 parameters	Δρmax = 0.48 e Å−3
1 restraint	Δρmin = −1.26 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	0.2500	0.2500	0.5000	0.0306 (3)
O1	0.21580 (12)	0.5058 (5)	0.6033 (3)	0.0482 (7)
O1W	0.26506 (15)	0.4700 (6)	0.3410 (3)	0.0706 (11)
H1W	0.2466	0.4915	0.2588	0.106*
H2W	0.2902	0.5473	0.3818	0.106*
O2	0.14621 (18)	0.7348 (5)	0.6067 (4)	0.0693 (12)
N1	0.17065 (13)	0.2015 (6)	0.4376 (3)	0.0363 (8)
H1N	0.1516	0.0810	0.4722	0.044*
C1	0.16898 (19)	0.5618 (7)	0.5671 (4)	0.0452 (10)
C2	0.13961 (16)	0.4099 (7)	0.4637 (4)	0.0417 (9)
H2	0.1387	0.4962	0.3805	0.050*
C3	0.08064 (17)	0.3674 (8)	0.5024 (4)	0.0482 (10)
H3	0.0632	0.5162	0.5115	0.058*
C4	0.0511 (2)	0.2376 (9)	0.3929 (6)	0.0711 (17)
H4A	0.0135	0.2290	0.4137	0.107*
H4B	0.0656	0.0865	0.3861	0.107*
H4C	0.0555	0.3157	0.3100	0.107*
C5	0.0749 (2)	0.2437 (8)	0.6330 (5)	0.0662 (15)
H5A	0.0899	0.0936	0.6255	0.099*
H5B	0.0376	0.2325	0.6551	0.099*
H5C	0.0936	0.3264	0.7013	0.099*

	U11	U22	U33	U12	U13	U23
Ni1	0.0303 (4)	0.0399 (4)	0.0215 (3)	−0.0096 (3)	−0.0074 (2)	0.0002 (3)
O1	0.0422 (16)	0.0578 (18)	0.0444 (15)	−0.0082 (14)	−0.0154 (13)	−0.0173 (14)
O1W	0.095 (3)	0.079 (2)	0.0377 (15)	−0.053 (2)	−0.0269 (16)	0.0222 (16)
O2	0.080 (3)	0.0384 (18)	0.089 (3)	0.0107 (16)	−0.022 (2)	−0.0196 (16)
N1	0.0307 (17)	0.0426 (19)	0.0356 (16)	−0.0079 (13)	−0.0048 (13)	−0.0087 (13)
C1	0.058 (3)	0.037 (2)	0.041 (2)	−0.010 (2)	−0.0073 (19)	−0.0010 (17)
C2	0.041 (2)	0.045 (2)	0.0385 (19)	−0.0071 (18)	−0.0112 (17)	0.0018 (17)
C3	0.037 (2)	0.045 (2)	0.063 (3)	0.0036 (18)	−0.004 (2)	−0.006 (2)
C4	0.044 (3)	0.099 (5)	0.070 (4)	−0.015 (3)	−0.018 (3)	−0.005 (3)
C5	0.066 (3)	0.074 (4)	0.058 (3)	−0.013 (2)	0.018 (3)	−0.013 (2)

Ni1—O1	2.019 (3)	C1—C2	1.550 (5)
Ni1—O1i	2.019 (3)	C2—C3	1.542 (6)
Ni1—N1	2.087 (3)	C2—H2	0.9800
Ni1—N1i	2.087 (3)	C3—C5	1.511 (6)
Ni1—O1Wi	2.095 (3)	C3—C4	1.525 (6)
Ni1—O1W	2.095 (3)	C3—H3	0.9800
O1—C1	1.262 (5)	C4—H4A	0.9600
O1W—H1W	0.9519	C4—H4B	0.9600
O1W—H2W	0.8736	C4—H4C	0.9600
O2—C1	1.231 (5)	C5—H5A	0.9600
N1—C2	1.472 (5)	C5—H5B	0.9600
N1—H1N	0.9209	C5—H5C	0.9600
O1—Ni1—O1i	180.00 (13)	N1—C2—C3	114.4 (3)
O1—Ni1—N1	81.68 (11)	N1—C2—C1	110.7 (3)
O1i—Ni1—N1	98.32 (11)	C3—C2—C1	111.6 (4)
O1—Ni1—N1i	98.32 (11)	N1—C2—H2	106.6
O1i—Ni1—N1i	81.68 (11)	C3—C2—H2	106.6
N1—Ni1—N1i	180.00 (6)	C1—C2—H2	106.6
O1—Ni1—O1Wi	89.15 (15)	C5—C3—C4	110.0 (4)
O1i—Ni1—O1Wi	90.85 (15)	C5—C3—C2	113.2 (4)
N1—Ni1—O1Wi	88.38 (13)	C4—C3—C2	110.7 (4)
N1i—Ni1—O1Wi	91.62 (13)	C5—C3—H3	107.6
O1—Ni1—O1W	90.85 (15)	C4—C3—H3	107.6
O1i—Ni1—O1W	89.15 (15)	C2—C3—H3	107.6
N1—Ni1—O1W	91.62 (13)	C3—C4—H4A	109.5
N1i—Ni1—O1W	88.38 (13)	C3—C4—H4B	109.5
O1Wi—Ni1—O1W	180.0	H4A—C4—H4B	109.5
C1—O1—Ni1	115.9 (2)	C3—C4—H4C	109.5
Ni1—O1W—H1W	131.2	H4A—C4—H4C	109.5
Ni1—O1W—H2W	95.2	H4B—C4—H4C	109.5
H1W—O1W—H2W	132.9	C3—C5—H5A	109.5
C2—N1—Ni1	109.2 (2)	C3—C5—H5B	109.5
C2—N1—H1N	107.4	H5A—C5—H5B	109.5
Ni1—N1—H1N	118.6	C3—C5—H5C	109.5
O2—C1—O1	123.2 (4)	H5A—C5—H5C	109.5
O2—C1—C2	118.5 (4)	H5B—C5—H5C	109.5
O1—C1—C2	118.3 (4)
O1i—Ni1—O1—C1	136 (100)	Ni1—O1—C1—C2	8.8 (5)
N1—Ni1—O1—C1	−15.6 (3)	Ni1—N1—C2—C3	−145.7 (3)
N1i—Ni1—O1—C1	164.4 (3)	Ni1—N1—C2—C1	−18.6 (4)
O1Wi—Ni1—O1—C1	−104.1 (3)	O2—C1—C2—N1	−174.8 (4)
O1W—Ni1—O1—C1	75.9 (3)	O1—C1—C2—N1	7.4 (5)
O1—Ni1—N1—C2	18.4 (2)	O2—C1—C2—C3	−46.2 (5)
O1i—Ni1—N1—C2	−161.6 (2)	O1—C1—C2—C3	136.0 (4)
N1i—Ni1—N1—C2	−115 (70)	N1—C2—C3—C5	65.0 (5)
O1Wi—Ni1—N1—C2	107.8 (3)	C1—C2—C3—C5	−61.6 (5)
O1W—Ni1—N1—C2	−72.2 (3)	N1—C2—C3—C4	−59.0 (5)
Ni1—O1—C1—O2	−168.9 (4)	C1—C2—C3—C4	174.4 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O2ii	0.92	2.45 (3)	3.286 (5)	152
O1W—H1W···O1iii	0.95	1.74	2.684 (4)	172
O1W—H2W···O2iv	0.87	2.04	2.856 (5)	155
C5—H5A···O2ii	0.96	2.53	3.483 (6)	170

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O2i	0.92	2.45 (3)	3.286 (5)	152
O1W—H1W⋯O1ii	0.95	1.74	2.684 (4)	172
O1W—H2W⋯O2iii	0.87	2.04	2.856 (5)	155
C5—H5A⋯O2i	0.96	2.53	3.483 (6)	170

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