Bis[2-(1-imino-eth-yl)phenolato-κN,O]nickel(II).

There are one and a half independent mol-ecules in the asymmetric unit of the title compound, [Ni(C(8)H(8)NO)(2)], one of which is situated on an inversion center. In both mol-ecules, the Ni(II) ion is coordinated by two O and two N atoms from two Schiff base ligands in an approximate square-planar geometry. Inter-molecular N-H⋯O hydrogen bonds link three mol-ecules into centrosymmetric trimer. The crystal packing exhibits weak inter-molecular C-H⋯O hydrogen bonds and voids of 37 Å(3).

Related literature

For general background to the use of Schiff bases in coord­in­ation chemistry, see: Haikarainen et al. (2001 ▶); Miyasaka et al. (2002 ▶). For nickel complexes with Schiff base ligands, see: Liu et al. (2006 ▶); Wang (2010 ▶). For the crystal structure of a similar copper(II) complex, see: Marongiu & Lingafelter (1971 ▶).

Experimental

Crystal data

[Ni(C8H8NO)2]

M = 327.02

Triclinic,

a = 9.1084 (10) Å

b = 11.3612 (16) Å

c = 11.8249 (18) Å

α = 101.006 (3)°

β = 93.049 (3)°

γ = 109.777 (3)°

V = 1121.1 (3) Å3

Z = 3

Mo Kα radiation

μ = 1.30 mm−1

T = 298 K

0.20 × 0.20 × 0.18 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ▶) T min = 0.781, T max = 0.799

6121 measured reflections

4190 independent reflections

2297 reflections with I > 2σ(I)

R int = 0.044

Refinement

R[F 2 > 2σ(F 2)] = 0.062

wR(F 2) = 0.146

S = 0.99

4190 reflections

298 parameters

3 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.48 e Å−3

Δρmin = −0.39 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; 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: SHELXTL.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811051476/cv5207sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811051476/cv5207Isup2.hkl

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

[Ni(C8H8NO)2]	Z = 3
Mr = 327.02	F(000) = 510
Triclinic, P1	Dx = 1.453 Mg m−3
a = 9.1084 (10) Å	Mo Kα radiation, λ = 0.71073 Å
b = 11.3612 (16) Å	Cell parameters from 772 reflections
c = 11.8249 (18) Å	θ = 2.3–24.5°
α = 101.006 (3)°	µ = 1.30 mm−1
β = 93.049 (3)°	T = 298 K
γ = 109.777 (3)°	Block, red
V = 1121.1 (3) Å3	0.20 × 0.20 × 0.18 mm

Bruker APEXII CCD area-detector diffractometer	4190 independent reflections
Radiation source: fine-focus sealed tube	2297 reflections with I > 2σ(I)
graphite	Rint = 0.044
ω scans	θmax = 25.7°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	h = −11→11
Tmin = 0.781, Tmax = 0.799	k = −13→13
6121 measured reflections	l = −13→14

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)] = 0.062	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.146	H atoms treated by a mixture of independent and constrained refinement
S = 0.99	w = 1/[σ2(Fo2) + (0.0585P)2] where P = (Fo2 + 2Fc2)/3
4190 reflections	(Δ/σ)max < 0.001
298 parameters	Δρmax = 0.48 e Å−3
3 restraints	Δρmin = −0.39 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	0.0392 (3)
Ni2	0.35993 (9)	0.05065 (7)	0.23238 (6)	0.0385 (3)
O1	0.1878 (5)	−0.0945 (3)	0.2135 (3)	0.0472 (11)
O2	0.5346 (5)	0.1953 (3)	0.2545 (3)	0.0473 (11)
O3	0.4558 (5)	0.4475 (3)	0.3430 (3)	0.0477 (11)
N1	0.2586 (6)	0.1539 (4)	0.3058 (4)	0.0423 (12)
N2	0.4618 (6)	−0.0507 (4)	0.1545 (4)	0.0423 (12)
N3	0.4211 (6)	0.6312 (4)	0.5050 (4)	0.0416 (12)
C1	0.0143 (7)	−0.0061 (6)	0.3199 (5)	0.0451 (15)
C2	0.0540 (7)	−0.1072 (6)	0.2547 (5)	0.0445 (16)
C3	−0.0595 (8)	−0.2330 (6)	0.2351 (6)	0.0571 (18)
H3	−0.0379	−0.3009	0.1913	0.069*
C4	−0.1993 (8)	−0.2566 (7)	0.2789 (6)	0.067 (2)
H4	−0.2708	−0.3403	0.2651	0.080*
C5	−0.2365 (9)	−0.1581 (8)	0.3436 (6)	0.070 (2)
H5	−0.3316	−0.1752	0.3741	0.084*
C6	−0.1317 (8)	−0.0350 (7)	0.3621 (6)	0.0594 (19)
H6	−0.1581	0.0314	0.4039	0.071*
C7	0.1213 (7)	0.1262 (6)	0.3398 (5)	0.0423 (15)
C8	0.0716 (8)	0.2323 (6)	0.4004 (6)	0.065 (2)
H8A	0.1536	0.3133	0.4047	0.098*
H8B	0.0519	0.2216	0.4775	0.098*
H8C	−0.0226	0.2298	0.3579	0.098*
C9	0.7050 (7)	0.1099 (6)	0.1411 (5)	0.0419 (15)
C10	0.6652 (7)	0.2101 (6)	0.2071 (5)	0.0433 (15)
C11	0.7740 (8)	0.3369 (6)	0.2241 (6)	0.0563 (18)
H11	0.7512	0.4047	0.2672	0.068*
C12	0.9132 (9)	0.3605 (7)	0.1774 (6)	0.066 (2)
H12	0.9839	0.4444	0.1908	0.080*
C13	0.9520 (9)	0.2637 (9)	0.1111 (7)	0.075 (2)
H13	1.0458	0.2816	0.0787	0.090*
C14	0.8479 (8)	0.1411 (7)	0.0948 (6)	0.0613 (19)
H14	0.8730	0.0752	0.0508	0.074*
C15	0.5979 (7)	−0.0231 (5)	0.1195 (5)	0.0396 (15)
C16	0.6453 (8)	−0.1295 (6)	0.0558 (5)	0.0563 (18)
H16A	0.5654	−0.2106	0.0551	0.084*
H16B	0.7430	−0.1254	0.0941	0.084*
H16C	0.6577	−0.1204	−0.0226	0.084*
C17	0.3474 (6)	0.6042 (5)	0.3019 (5)	0.0354 (14)
C18	0.3980 (7)	0.4986 (5)	0.2679 (5)	0.0412 (15)
C19	0.3859 (7)	0.4450 (6)	0.1502 (5)	0.0491 (16)
H19	0.4205	0.3770	0.1271	0.059*
C20	0.3235 (8)	0.4911 (6)	0.0672 (6)	0.0562 (18)
H20	0.3155	0.4532	−0.0109	0.067*
C21	0.2730 (8)	0.5925 (6)	0.0987 (6)	0.0567 (18)
H21	0.2314	0.6234	0.0422	0.068*
C22	0.2843 (7)	0.6477 (6)	0.2141 (6)	0.0474 (16)
H22	0.2494	0.7159	0.2348	0.057*
C23	0.3618 (6)	0.6684 (5)	0.4228 (5)	0.0368 (14)
C24	0.3106 (9)	0.7818 (6)	0.4540 (5)	0.066 (2)
H24A	0.3309	0.8143	0.5366	0.099*
H24B	0.2000	0.7559	0.4291	0.099*
H24C	0.3680	0.8477	0.4161	0.099*
H1	0.306 (7)	0.2400 (13)	0.325 (5)	0.080*
H2	0.399 (6)	−0.134 (2)	0.139 (5)	0.080*
H3A	0.434 (8)	0.676 (5)	0.578 (2)	0.080*

	U11	U22	U33	U12	U13	U23
Ni1	0.0459 (7)	0.0321 (6)	0.0439 (7)	0.0225 (6)	0.0028 (6)	0.0035 (5)
Ni2	0.0378 (5)	0.0330 (5)	0.0473 (5)	0.0168 (4)	0.0084 (4)	0.0063 (4)
O1	0.038 (2)	0.038 (2)	0.067 (3)	0.018 (2)	0.012 (2)	0.006 (2)
O2	0.045 (3)	0.037 (2)	0.057 (3)	0.016 (2)	0.016 (2)	−0.001 (2)
O3	0.069 (3)	0.041 (2)	0.041 (3)	0.034 (2)	−0.001 (2)	0.003 (2)
N1	0.047 (3)	0.035 (3)	0.044 (3)	0.017 (3)	0.003 (3)	0.004 (3)
N2	0.043 (3)	0.036 (3)	0.049 (3)	0.015 (3)	0.015 (3)	0.006 (3)
N3	0.046 (3)	0.038 (3)	0.044 (3)	0.024 (3)	0.000 (3)	0.003 (3)
C1	0.036 (4)	0.054 (4)	0.050 (4)	0.022 (3)	0.004 (3)	0.014 (3)
C2	0.036 (4)	0.046 (4)	0.058 (4)	0.018 (3)	0.005 (3)	0.023 (3)
C3	0.044 (4)	0.053 (4)	0.076 (5)	0.016 (4)	0.003 (4)	0.020 (4)
C4	0.044 (5)	0.069 (5)	0.079 (6)	0.001 (4)	0.001 (4)	0.033 (4)
C5	0.048 (5)	0.088 (6)	0.078 (6)	0.024 (5)	0.020 (4)	0.025 (5)
C6	0.045 (4)	0.073 (5)	0.067 (5)	0.026 (4)	0.014 (4)	0.021 (4)
C7	0.049 (4)	0.053 (4)	0.032 (4)	0.031 (4)	0.004 (3)	0.005 (3)
C8	0.058 (5)	0.069 (5)	0.077 (5)	0.038 (4)	0.015 (4)	0.004 (4)
C9	0.039 (4)	0.047 (4)	0.042 (4)	0.019 (3)	0.004 (3)	0.008 (3)
C10	0.043 (4)	0.045 (4)	0.039 (4)	0.012 (3)	−0.002 (3)	0.010 (3)
C11	0.047 (4)	0.049 (4)	0.067 (5)	0.012 (4)	0.003 (4)	0.012 (4)
C12	0.054 (5)	0.065 (5)	0.068 (5)	0.001 (4)	0.005 (4)	0.023 (4)
C13	0.044 (5)	0.102 (7)	0.069 (6)	0.010 (5)	0.011 (4)	0.020 (5)
C14	0.042 (4)	0.080 (5)	0.062 (5)	0.024 (4)	0.013 (4)	0.011 (4)
C15	0.045 (4)	0.045 (4)	0.036 (4)	0.024 (3)	0.002 (3)	0.013 (3)
C16	0.066 (5)	0.056 (4)	0.059 (4)	0.038 (4)	0.020 (4)	0.010 (4)
C17	0.028 (3)	0.032 (3)	0.046 (4)	0.012 (3)	0.004 (3)	0.006 (3)
C18	0.036 (4)	0.038 (3)	0.051 (4)	0.015 (3)	0.011 (3)	0.011 (3)
C19	0.056 (4)	0.047 (4)	0.043 (4)	0.021 (3)	0.006 (3)	0.004 (3)
C20	0.058 (4)	0.059 (4)	0.040 (4)	0.010 (4)	−0.001 (4)	0.006 (4)
C21	0.058 (5)	0.059 (5)	0.056 (5)	0.019 (4)	0.001 (4)	0.026 (4)
C22	0.046 (4)	0.045 (4)	0.056 (5)	0.018 (3)	0.006 (3)	0.019 (3)
C23	0.032 (3)	0.030 (3)	0.050 (4)	0.013 (3)	0.010 (3)	0.007 (3)
C24	0.102 (6)	0.063 (4)	0.059 (5)	0.062 (5)	0.017 (4)	0.013 (4)

Ni1—O3i	1.816 (4)	C8—H8C	0.9600
Ni1—O3	1.816 (4)	C9—C14	1.398 (8)
Ni1—N3	1.853 (5)	C9—C10	1.417 (8)
Ni1—N3i	1.853 (5)	C9—C15	1.459 (8)
Ni2—O1	1.817 (4)	C10—C11	1.414 (8)
Ni2—O2	1.822 (4)	C11—C12	1.374 (9)
Ni2—N1	1.847 (5)	C11—H11	0.9300
Ni2—N2	1.856 (5)	C12—C13	1.382 (10)
O1—C2	1.310 (7)	C12—H12	0.9300
O2—C10	1.315 (7)	C13—C14	1.364 (9)
O3—C18	1.326 (6)	C13—H13	0.9300
N1—C7	1.289 (7)	C14—H14	0.9300
N1—H1	0.902 (10)	C15—C16	1.501 (7)
N2—C15	1.283 (7)	C16—H16A	0.9600
N2—H2	0.899 (10)	C16—H16B	0.9600
N3—C23	1.294 (7)	C16—H16C	0.9600
N3—H3A	0.897 (10)	C17—C22	1.406 (7)
C1—C6	1.400 (8)	C17—C18	1.422 (7)
C1—C2	1.420 (8)	C17—C23	1.453 (7)
C1—C7	1.454 (8)	C18—C19	1.391 (8)
C2—C3	1.418 (8)	C19—C20	1.378 (8)
C3—C4	1.361 (9)	C19—H19	0.9300
C3—H3	0.9300	C20—C21	1.375 (8)
C4—C5	1.383 (9)	C20—H20	0.9300
C4—H4	0.9300	C21—C22	1.371 (8)
C5—C6	1.369 (9)	C21—H21	0.9300
C5—H5	0.9300	C22—H22	0.9300
C6—H6	0.9300	C23—C24	1.502 (7)
C7—C8	1.498 (8)	C24—H24A	0.9600
C8—H8A	0.9600	C24—H24B	0.9600
C8—H8B	0.9600	C24—H24C	0.9600
O3i—Ni1—O3	180.000 (1)	C10—C9—C15	120.8 (5)
O3i—Ni1—N3	86.81 (18)	O2—C10—C11	116.8 (6)
O3—Ni1—N3	93.19 (18)	O2—C10—C9	125.4 (5)
O3i—Ni1—N3i	93.19 (18)	C11—C10—C9	117.9 (6)
O3—Ni1—N3i	86.81 (18)	C12—C11—C10	120.3 (7)
N3—Ni1—N3i	180.000 (2)	C12—C11—H11	119.8
O1—Ni2—O2	178.57 (18)	C10—C11—H11	119.8
O1—Ni2—N1	93.24 (19)	C11—C12—C13	122.3 (7)
O2—Ni2—N1	87.0 (2)	C11—C12—H12	118.9
O1—Ni2—N2	87.43 (19)	C13—C12—H12	118.9
O2—Ni2—N2	92.39 (19)	C14—C13—C12	117.7 (7)
N1—Ni2—N2	178.2 (2)	C14—C13—H13	121.2
C2—O1—Ni2	127.8 (4)	C12—C13—H13	121.2
C10—O2—Ni2	127.8 (4)	C13—C14—C9	123.1 (7)
C18—O3—Ni1	129.2 (4)	C13—C14—H14	118.4
C7—N1—Ni2	131.3 (4)	C9—C14—H14	118.4
C7—N1—H1	108 (4)	N2—C15—C9	120.5 (5)
Ni2—N1—H1	121 (4)	N2—C15—C16	119.1 (5)
C15—N2—Ni2	132.2 (4)	C9—C15—C16	120.4 (5)
C15—N2—H2	118 (4)	C15—C16—H16A	109.5
Ni2—N2—H2	110 (4)	C15—C16—H16B	109.5
C23—N3—Ni1	131.0 (4)	H16A—C16—H16B	109.5
C23—N3—H3A	119 (4)	C15—C16—H16C	109.5
Ni1—N3—H3A	110 (4)	H16A—C16—H16C	109.5
C6—C1—C2	119.1 (6)	H16B—C16—H16C	109.5
C6—C1—C7	120.2 (6)	C22—C17—C18	118.0 (5)
C2—C1—C7	120.6 (5)	C22—C17—C23	119.9 (5)
O1—C2—C3	117.3 (6)	C18—C17—C23	122.1 (5)
O1—C2—C1	125.5 (5)	O3—C18—C19	117.8 (5)
C3—C2—C1	117.2 (6)	O3—C18—C17	123.3 (5)
C4—C3—C2	121.7 (7)	C19—C18—C17	118.9 (5)
C4—C3—H3	119.2	C20—C19—C18	121.1 (6)
C2—C3—H3	119.2	C20—C19—H19	119.5
C3—C4—C5	121.0 (7)	C18—C19—H19	119.5
C3—C4—H4	119.5	C21—C20—C19	120.8 (6)
C5—C4—H4	119.5	C21—C20—H20	119.6
C6—C5—C4	119.2 (7)	C19—C20—H20	119.6
C6—C5—H5	120.4	C22—C21—C20	119.4 (6)
C4—C5—H5	120.4	C22—C21—H21	120.3
C5—C6—C1	121.9 (7)	C20—C21—H21	120.3
C5—C6—H6	119.0	C21—C22—C17	121.9 (6)
C1—C6—H6	119.0	C21—C22—H22	119.1
N1—C7—C1	121.0 (5)	C17—C22—H22	119.1
N1—C7—C8	119.3 (6)	N3—C23—C17	121.1 (5)
C1—C7—C8	119.7 (6)	N3—C23—C24	118.8 (5)
C7—C8—H8A	109.5	C17—C23—C24	120.1 (5)
C7—C8—H8B	109.5	C23—C24—H24A	109.5
H8A—C8—H8B	109.5	C23—C24—H24B	109.5
C7—C8—H8C	109.5	H24A—C24—H24B	109.5
H8A—C8—H8C	109.5	C23—C24—H24C	109.5
H8B—C8—H8C	109.5	H24A—C24—H24C	109.5
C14—C9—C10	118.7 (6)	H24B—C24—H24C	109.5
C14—C9—C15	120.5 (6)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···O2i	0.90 (1)	2.16 (2)	3.055 (6)	172 (6)
N1—H1···O3	0.90 (1)	2.25 (2)	3.138 (6)	168 (6)
C22—H22···O1ii	0.93	2.46	3.332 (6)	157 (6)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3A⋯O2i	0.90 (1)	2.16 (2)	3.055 (6)	172 (6)
N1—H1⋯O3	0.90 (1)	2.25 (2)	3.138 (6)	168 (6)
C22—H22⋯O1ii	0.93	2.46	3.332 (6)	157 (6)

Symmetry codes: (i) ; (ii) .