Bis{2-(5-hydr-oxy-2-[1-(hydroxy-imino)eth-yl]phenolato-κO,N}nickel(II) N,N-dimethyl-formamide disolvate.

The Ni atom of the title complex, [Ni(C(8)H(8)NO(3))(2)]·2C(3)H(7)NO, lies on a center of inversion in a square-planar N(2)O(2) coordination environment. An intra-molecular O-H⋯O hydrogen bond exists between the oximic hydr-oxy group of one ligand and the metal-coordinated O atom of the symmetry-related ligand. The dimethyl-formamide solvent mol-ecules are connected to the phenolate groups of the complex via O-H⋯O hydrogen bonds.

Related literature

For general background to the applications of 2-hydroxy­aryl­oxime complexes in extractive metallurgy and biology, see: Keeney et al. (1984 ▶); Elo & Lumme (1985 ▶); Chaudhuri (2003 ▶); Milios et al. (2007 ▶). For related structures, see: Hatzidimitriou et al. (1997 ▶); Voutsas et al. (1999 ▶).

Experimental

Crystal data

[Ni(C8H8NO3)2]·2C3H7NO

M = 537.21

Monoclinic,

a = 13.2905 (10) Å

b = 5.8649 (4) Å

c = 15.9345 (12) Å

β = 99.129 (1)°

V = 1226.32 (16) Å3

Z = 2

Mo Kα radiation

μ = 0.85 mm−1

T = 295 K

0.50 × 0.40 × 0.30 mm

Data collection

Bruker SMART APEX area-detector diffractometer

Absorption correction: multi-scan (SADABS, Bruker, 2002 ▶) T min = 0.677, T max = 0.786

6243 measured reflections

2398 independent reflections

2067 reflections with I > 2σ(I)

R int = 0.017

Refinement

R[F 2 > 2σ(F 2)] = 0.028

wR(F 2) = 0.083

S = 1.04

2398 reflections

160 parameters

H-atom parameters constrained

Δρmax = 0.25 e Å−3

Δρmin = −0.20 e Å−3

Data collection: SMART (Bruker, 2002 ▶); cell refinement: SAINT (Bruker, 2002 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); 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/S1600536809039257/tk2537sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809039257/tk2537Isup2.hkl

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

[Ni(C8H8NO3)2]·2C3H7NO	F(000) = 564
Mr = 537.21	Dx = 1.455 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5624 reflections
a = 13.2905 (10) Å	θ = 2.2–26.5°
b = 5.8649 (4) Å	µ = 0.85 mm−1
c = 15.9345 (12) Å	T = 295 K
β = 99.129 (1)°	Block, brown
V = 1226.32 (16) Å3	0.50 × 0.40 × 0.30 mm
Z = 2

Bruker SMART APEX area-detector diffractometer	2398 independent reflections
Radiation source: fine-focus sealed tube	2067 reflections with I > 2σ(I)
graphite	Rint = 0.017
φ and ω scans	θmax = 26.0°, θmin = 2.6°
Absorption correction: multi-scan (SADABS, Bruker, 2002)	h = −16→14
Tmin = 0.677, Tmax = 0.786	k = −7→6
6243 measured reflections	l = −19→13

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)] = 0.028	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.083	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0436P)2 + 0.4293P] where P = (Fo2 + 2Fc2)/3
2398 reflections	(Δ/σ)max < 0.001
160 parameters	Δρmax = 0.25 e Å−3
0 restraints	Δρmin = −0.20 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	0.0000	0.0000	0.03529 (12)
O1	0.36927 (11)	0.3031 (3)	0.28775 (9)	0.0573 (4)
H1	0.3831	0.4080	0.3217	0.086*
O2	0.11298 (11)	0.0218 (2)	0.08068 (10)	0.0512 (4)
O3	−0.16273 (10)	0.2912 (3)	0.00960 (10)	0.0600 (4)
H3	−0.1806	0.1977	−0.0281	0.090*
O4	0.45924 (14)	0.6291 (3)	0.38447 (11)	0.0733 (5)
N1	−0.06182 (11)	0.2487 (3)	0.04612 (10)	0.0401 (4)
N2	0.57279 (13)	0.9128 (3)	0.41807 (11)	0.0477 (4)
C1	0.14012 (14)	0.1839 (3)	0.13806 (11)	0.0370 (4)
C2	0.23725 (14)	0.1673 (3)	0.18586 (11)	0.0412 (4)
H2	0.2786	0.0444	0.1773	0.049*
C3	0.27296 (14)	0.3301 (3)	0.24559 (12)	0.0412 (4)
C4	0.21144 (16)	0.5124 (3)	0.26013 (14)	0.0472 (5)
H4	0.2350	0.6225	0.3005	0.057*
C5	0.11510 (16)	0.5279 (3)	0.21400 (13)	0.0444 (4)
H5	0.0744	0.6507	0.2241	0.053*
C6	0.07536 (14)	0.3672 (3)	0.15236 (11)	0.0359 (4)
C7	−0.02770 (14)	0.3901 (3)	0.10657 (11)	0.0371 (4)
C8	−0.09685 (17)	0.5748 (4)	0.12913 (15)	0.0539 (5)
H8A	−0.1664	0.5247	0.1164	0.081*
H8B	−0.0880	0.7094	0.0968	0.081*
H8C	−0.0804	0.6085	0.1887	0.081*
C9	0.62892 (19)	0.7952 (4)	0.49118 (15)	0.0622 (6)
H9A	0.6381	0.8958	0.5393	0.093*
H9B	0.6943	0.7492	0.4787	0.093*
H9C	0.5914	0.6631	0.5038	0.093*
C10	0.60887 (19)	1.1364 (4)	0.39838 (18)	0.0678 (7)
H10A	0.6067	1.2368	0.4456	0.102*
H10B	0.5662	1.1957	0.3490	0.102*
H10C	0.6777	1.1248	0.3875	0.102*
C11	0.49409 (16)	0.8175 (4)	0.37059 (14)	0.0533 (5)
H11	0.4626	0.8977	0.3233	0.064*

	U11	U22	U33	U12	U13	U23
Ni1	0.03338 (19)	0.0364 (2)	0.03341 (19)	0.00408 (13)	−0.00300 (12)	−0.00579 (13)
O1	0.0471 (8)	0.0590 (9)	0.0575 (9)	0.0005 (7)	−0.0175 (7)	−0.0137 (7)
O2	0.0461 (8)	0.0486 (8)	0.0520 (8)	0.0128 (6)	−0.0136 (6)	−0.0206 (6)
O3	0.0393 (8)	0.0685 (10)	0.0646 (10)	0.0185 (7)	−0.0148 (7)	−0.0263 (8)
O4	0.0707 (11)	0.0620 (11)	0.0790 (12)	−0.0240 (9)	−0.0133 (9)	−0.0079 (9)
N1	0.0331 (8)	0.0433 (8)	0.0408 (8)	0.0070 (6)	−0.0033 (6)	−0.0046 (7)
N2	0.0420 (9)	0.0450 (9)	0.0548 (10)	−0.0038 (7)	0.0031 (7)	−0.0094 (8)
C1	0.0397 (9)	0.0376 (9)	0.0319 (9)	−0.0009 (8)	0.0000 (7)	−0.0030 (7)
C2	0.0403 (10)	0.0417 (10)	0.0394 (10)	0.0037 (8)	−0.0005 (8)	−0.0039 (8)
C3	0.0404 (10)	0.0440 (10)	0.0364 (9)	−0.0059 (8)	−0.0018 (8)	0.0010 (8)
C4	0.0500 (11)	0.0434 (11)	0.0453 (11)	−0.0072 (9)	−0.0013 (9)	−0.0120 (8)
C5	0.0466 (11)	0.0396 (10)	0.0460 (11)	0.0014 (8)	0.0041 (9)	−0.0084 (8)
C6	0.0391 (9)	0.0363 (9)	0.0319 (9)	−0.0004 (7)	0.0046 (7)	−0.0007 (7)
C7	0.0415 (10)	0.0370 (10)	0.0330 (9)	0.0036 (8)	0.0069 (7)	−0.0004 (7)
C8	0.0506 (12)	0.0528 (12)	0.0563 (13)	0.0135 (10)	0.0025 (10)	−0.0134 (10)
C9	0.0567 (13)	0.0743 (16)	0.0517 (13)	−0.0062 (12)	−0.0034 (10)	−0.0073 (11)
C10	0.0595 (14)	0.0498 (13)	0.0917 (19)	−0.0088 (11)	0.0048 (13)	−0.0066 (12)
C11	0.0470 (11)	0.0536 (12)	0.0553 (12)	−0.0024 (10)	−0.0046 (9)	−0.0093 (10)

Ni1—O2i	1.8197 (14)	C3—C4	1.387 (3)
Ni1—O2	1.8197 (14)	C4—C5	1.375 (3)
Ni1—N1i	1.8801 (15)	C4—H4	0.9300
Ni1—N1	1.8801 (15)	C5—C6	1.403 (3)
O1—C3	1.357 (2)	C5—H5	0.9300
O1—H1	0.8200	C6—C7	1.452 (2)
O2—C1	1.328 (2)	C7—C8	1.501 (3)
O3—N1	1.3970 (19)	C8—H8A	0.9600
O3—H3	0.8200	C8—H8B	0.9600
O4—C11	1.232 (3)	C8—H8C	0.9600
N1—C7	1.297 (2)	C9—H9A	0.9600
N2—C11	1.315 (3)	C9—H9B	0.9600
N2—C10	1.447 (3)	C9—H9C	0.9600
N2—C9	1.454 (3)	C10—H10A	0.9600
C1—C2	1.394 (2)	C10—H10B	0.9600
C1—C6	1.418 (2)	C10—H10C	0.9600
C2—C3	1.378 (3)	C11—H11	0.9300
C2—H2	0.9300
O2i—Ni1—O2	180.00 (14)	C6—C5—H5	118.5
O2i—Ni1—N1i	91.84 (6)	C5—C6—C1	116.83 (17)
O2—Ni1—N1i	88.16 (6)	C5—C6—C7	120.64 (16)
O2i—Ni1—N1	88.16 (6)	C1—C6—C7	122.52 (16)
O2—Ni1—N1	91.84 (6)	N1—C7—C6	120.30 (16)
N1i—Ni1—N1	180.00 (11)	N1—C7—C8	118.96 (17)
C3—O1—H1	109.5	C6—C7—C8	120.74 (16)
C1—O2—Ni1	129.80 (12)	C7—C8—H8A	109.5
N1—O3—H3	109.5	C7—C8—H8B	109.5
C7—N1—O3	113.25 (14)	H8A—C8—H8B	109.5
C7—N1—Ni1	131.56 (13)	C7—C8—H8C	109.5
O3—N1—Ni1	115.19 (11)	H8A—C8—H8C	109.5
C11—N2—C10	121.4 (2)	H8B—C8—H8C	109.5
C11—N2—C9	121.3 (2)	N2—C9—H9A	109.5
C10—N2—C9	117.25 (18)	N2—C9—H9B	109.5
O2—C1—C2	116.94 (16)	H9A—C9—H9B	109.5
O2—C1—C6	123.20 (16)	N2—C9—H9C	109.5
C2—C1—C6	119.86 (16)	H9A—C9—H9C	109.5
C3—C2—C1	121.11 (17)	H9B—C9—H9C	109.5
C3—C2—H2	119.4	N2—C10—H10A	109.5
C1—C2—H2	119.4	N2—C10—H10B	109.5
O1—C3—C2	117.08 (17)	H10A—C10—H10B	109.5
O1—C3—C4	122.81 (17)	N2—C10—H10C	109.5
C2—C3—C4	120.11 (17)	H10A—C10—H10C	109.5
C5—C4—C3	119.03 (17)	H10B—C10—H10C	109.5
C5—C4—H4	120.5	O4—C11—N2	124.5 (2)
C3—C4—H4	120.5	O4—C11—H11	117.8
C4—C5—C6	123.04 (18)	N2—C11—H11	117.8
C4—C5—H5	118.5

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O4	0.82	1.84	2.622 (2)	159
O3—H3···O2i	0.82	1.85	2.4857 (19)	134

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O4	0.82	1.84	2.622 (2)	159
O3—H3⋯O2i	0.82	1.85	2.4857 (19)	134

Symmetry code: (i) .