Diaquabis-[3-(hydroxy-imino-)butanoato]nickel(II): a triclinic polymorph.

The title centrosymmetric mononuclear complex, [Ni(C(4)H(6)NO(3))(2)(H(2)O)(2)], is a polymorph of the previously reported complex [Dudarenko et al. (2010 ▶). Acta Cryst. E66, m277-m278]. The Ni(II) atom, lying on an inversion center, is six-coordinated by two carboxyl-ate O atoms and two oxime N atoms from two trans-disposed chelating 3-hydroxy-imino-butanoate ligands and two axial water mol-ecules in a distorted octa-hedral geometry. The hydr-oxy group forms an intra-molecular hydrogen bond with the coordinated carboxyl-ate O atom. The complex mol-ecules are linked in stacks along [010] by a hydrogen bond between the water O atom and the carboxyl-ate O atom of a neighboring mol-ecule. The stacks are further linked by O-H⋯O hydrogen bonds into a layer parallel to (001).

Related literature

For the monoclinic polymorph of the title compound, see: Dudarenko et al. (2010 ▶). For the coordination chemistry of hydroxy­imino­carboxylic acids and their derivatives, see: Duda et al. (1997 ▶); Mokhir et al. (2002 ▶); Moroz et al. (2008 ▶); Onindo et al. (1995 ▶). For 2-hydroxy­imino­carboxylic acids as efficient metal chelators, see: Gumienna-Kontecka et al. (2000 ▶); Sliva et al. (1997a ▶,b ▶). For the use of 2-hydroxy­imino­carboxylic acid derivatives as efficient ligands for stabilization of high oxidation states of transitional metals, see: Fritsky et al. (2006 ▶); Kanderal et al. (2005 ▶). For structures with monodentately coordinated carboxyl­ate groups, see: Wörl et al. (2005a ▶,b ▶). For the ligand synthesis, see: Khromov (1950 ▶).

Experimental

Crystal data

[Ni(C4H6NO3)2(H2O)2]

M = 326.92

Triclinic,

a = 5.5621 (14) Å

b = 7.340 (2) Å

c = 8.2979 (15) Å

α = 90.71 (2)°

β = 92.290 (18)°

γ = 112.18 (2)°

V = 313.31 (14) Å3

Z = 1

Mo Kα radiation

μ = 1.59 mm−1

T = 120 K

0.22 × 0.14 × 0.10 mm

Data collection

Nonius KappaCCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.764, T max = 0.856

2755 measured reflections

1223 independent reflections

1054 reflections with I > 2σ(I)

R int = 0.063

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.083

S = 0.98

1223 reflections

101 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.37 e Å−3

Δρmin = −0.35 e Å−3

Data collection: COLLECT (Nonius, 1998 ▶); cell refinement: DENZO/SCALEPACK (Otwinowski & Minor, 1997 ▶); data reduction: DENZO/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 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810006306/hy2284sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810006306/hy2284Isup2.hkl

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

[Ni(C4H6NO3)2(H2O)2]	Z = 1
Mr = 326.92	F(000) = 170
Triclinic, P1	Dx = 1.733 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.5621 (14) Å	Cell parameters from 1225 reflections
b = 7.340 (2) Å	θ = 3.9–36.0°
c = 8.2979 (15) Å	µ = 1.59 mm−1
α = 90.71 (2)°	T = 120 K
β = 92.290 (18)°	Block, dark pink
γ = 112.18 (2)°	0.22 × 0.14 × 0.10 mm
V = 313.31 (14) Å3

Nonius KappaCCD diffractometer	1223 independent reflections
Radiation source: fine-focus sealed tube	1054 reflections with I > 2σ(I)
horizontally mounted graphite crystal	Rint = 0.063
Detector resolution: 9 pixels mm-1	θmax = 26.0°, θmin = 3.8°
φ and ω scans with κ offset	h = −6→6
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −9→9
Tmin = 0.764, Tmax = 0.856	l = −10→10
2755 measured reflections

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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.083	H atoms treated by a mixture of independent and constrained refinement
S = 0.98	w = 1/[σ2(Fo2) + (0.0431P)2] where P = (Fo2 + 2Fc2)/3
1223 reflections	(Δ/σ)max < 0.001
101 parameters	Δρmax = 0.37 e Å−3
0 restraints	Δρmin = −0.35 e Å−3

	x	y	z	Uiso*/Ueq
Ni1	0.0000	0.0000	0.0000	0.0293 (2)
O1	−0.1803 (4)	0.1846 (3)	0.0358 (2)	0.0363 (5)
O2	−0.2828 (4)	0.4116 (3)	0.1563 (3)	0.0418 (5)
O3	0.3067 (5)	−0.0513 (4)	0.2814 (3)	0.0521 (7)
O4	0.3222 (4)	0.2337 (3)	−0.0904 (3)	0.0349 (5)
N1	0.1703 (4)	0.0643 (3)	0.2262 (3)	0.0309 (5)
C1	−0.1519 (5)	0.3071 (4)	0.1501 (3)	0.0298 (6)
C2	0.0492 (7)	0.3370 (6)	0.2868 (4)	0.0537 (9)
H2A	0.1902	0.4608	0.2678	0.064*
H2B	−0.0298	0.3578	0.3840	0.064*
C3	0.1734 (5)	0.1944 (4)	0.3286 (3)	0.0304 (6)
C4	0.3120 (7)	0.2237 (5)	0.4912 (3)	0.0452 (8)
H4A	0.2952	0.0982	0.5328	0.068*
H4B	0.2369	0.2883	0.5635	0.068*
H4C	0.4926	0.3033	0.4816	0.068*
H1O	0.315 (8)	−0.112 (6)	0.210 (5)	0.065 (14)*
H4O1	0.428 (9)	0.268 (7)	−0.018 (6)	0.081 (16)*
H4O2	0.284 (8)	0.322 (7)	−0.111 (5)	0.063 (13)*

	U11	U22	U33	U12	U13	U23
Ni1	0.0312 (3)	0.0324 (3)	0.0284 (3)	0.0174 (2)	−0.00632 (19)	−0.00037 (19)
O1	0.0400 (12)	0.0406 (12)	0.0364 (10)	0.0259 (10)	−0.0105 (8)	−0.0039 (9)
O2	0.0405 (12)	0.0347 (11)	0.0583 (12)	0.0242 (10)	−0.0057 (10)	−0.0012 (10)
O3	0.0778 (18)	0.0612 (17)	0.0394 (12)	0.0541 (15)	−0.0208 (11)	−0.0069 (11)
O4	0.0372 (13)	0.0324 (12)	0.0378 (11)	0.0169 (10)	−0.0043 (9)	0.0020 (9)
N1	0.0321 (13)	0.0348 (13)	0.0310 (11)	0.0189 (11)	−0.0046 (9)	0.0061 (10)
C1	0.0267 (14)	0.0253 (14)	0.0384 (14)	0.0112 (12)	−0.0005 (11)	0.0044 (11)
C2	0.060 (2)	0.053 (2)	0.058 (2)	0.0357 (18)	−0.0244 (16)	−0.0216 (16)
C3	0.0286 (14)	0.0334 (15)	0.0288 (13)	0.0116 (12)	−0.0020 (11)	0.0017 (11)
C4	0.055 (2)	0.0475 (19)	0.0314 (15)	0.0186 (16)	−0.0112 (13)	−0.0036 (13)

Ni1—O1	1.992 (2)	N1—C3	1.265 (4)
Ni1—N1	2.035 (2)	C1—C2	1.514 (4)
Ni1—O4	2.130 (2)	C2—C3	1.493 (4)
O1—C1	1.262 (4)	C2—H2A	0.9700
O2—C1	1.243 (4)	C2—H2B	0.9700
O3—N1	1.405 (3)	C3—C4	1.499 (4)
O3—H1O	0.75 (4)	C4—H4A	0.9600
O4—H4O1	0.79 (5)	C4—H4B	0.9600
O4—H4O2	0.77 (5)	C4—H4C	0.9600
O1i—Ni1—O1	180.00 (13)	C3—N1—Ni1	130.1 (2)
O1i—Ni1—N1	89.62 (9)	O3—N1—Ni1	116.79 (18)
O1—Ni1—N1	90.38 (9)	O2—C1—O1	122.5 (3)
O1i—Ni1—N1i	90.38 (9)	O2—C1—C2	116.2 (3)
O1—Ni1—N1i	89.62 (9)	O1—C1—C2	121.3 (3)
N1—Ni1—N1i	180.00 (15)	C3—C2—C1	124.7 (3)
O1i—Ni1—O4i	90.13 (9)	C3—C2—H2A	106.1
O1—Ni1—O4i	89.87 (9)	C1—C2—H2A	106.1
N1—Ni1—O4i	90.34 (9)	C3—C2—H2B	106.1
N1i—Ni1—O4i	89.66 (9)	C1—C2—H2B	106.1
O1i—Ni1—O4	89.87 (9)	H2A—C2—H2B	106.3
O1—Ni1—O4	90.13 (9)	N1—C3—C2	120.3 (2)
N1—Ni1—O4	89.66 (9)	N1—C3—C4	123.3 (3)
N1i—Ni1—O4	90.34 (9)	C2—C3—C4	116.3 (3)
O4i—Ni1—O4	180.00 (15)	C3—C4—H4A	109.5
C1—O1—Ni1	130.05 (18)	C3—C4—H4B	109.5
N1—O3—H1O	106 (3)	H4A—C4—H4B	109.5
Ni1—O4—H4O1	106 (3)	C3—C4—H4C	109.5
Ni1—O4—H4O2	111 (3)	H4A—C4—H4C	109.5
H4O1—O4—H4O2	107 (4)	H4B—C4—H4C	109.5
C3—N1—O3	113.1 (2)
Ni1—O1—C1—O2	−179.15 (18)	Ni1—N1—C3—C2	−3.3 (4)
Ni1—O1—C1—C2	1.9 (4)	O3—N1—C3—C4	0.8 (4)
O2—C1—C2—C3	162.2 (3)	Ni1—N1—C3—C4	−179.4 (2)
O1—C1—C2—C3	−18.8 (5)	C1—C2—C3—N1	19.2 (5)
O3—N1—C3—C2	176.9 (3)	C1—C2—C3—C4	−164.4 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H1O···O1i	0.75 (4)	2.14 (4)	2.766 (3)	142 (4)
O4—H4O1···O2ii	0.79 (5)	2.07 (5)	2.851 (3)	169 (5)
O4—H4O1···O1ii	0.79 (5)	2.50 (5)	3.068 (3)	130 (4)
O4—H4O2···O2iii	0.77 (5)	2.00 (5)	2.754 (3)	166 (4)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H1O⋯O1i	0.75 (4)	2.14 (4)	2.766 (3)	142 (4)
O4—H4O1⋯O2ii	0.79 (5)	2.07 (5)	2.851 (3)	169 (5)
O4—H4O1⋯O1ii	0.79 (5)	2.50 (5)	3.068 (3)	130 (4)
O4—H4O2⋯O2iii	0.77 (5)	2.00 (5)	2.754 (3)	166 (4)

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