Bis{μ-2,2'-[ethane-1,2-diylbis(nitrilo-methyl-idyne)]diphenolato}dinickel(II).

The asymmetric unit of the title compound, [Ni(2)(C(16)H(14)N(2)O(2))(2)], contains an Ni(II) cation which is coordinated by two imine N atoms and by two phenolate O atoms of the salen ligand {salen = N,N'-bis-(salicyl-idene)ethane-1,2-diamine or 2,2'-[ethane-1,2-diyl-bis(nitrilo-methyl-idyne)]diphenol}, leading to a distorted square-planar conformation. When a secondary Ni-O inter-action > 2.41 Å to the neighbouring phenolate O atom is considered, two mol-ecules are linked into a centrosymmetric dimer with an overall square-pyramidal coordination for the Ni(II) cation. Weak π-π inter-actions with a shortest interplanar distance of 3.704 Å help to stabilize the crystal structure.

Related literature

For a review on metal–salen complexes used in catalysis, see: Cozzi (2004 ▶).

Experimental

Crystal data

[Ni2(C16H14N2O2)2]

M = 650.00

Monoclinic,

a = 26.639 (2) Å

b = 6.9775 (6) Å

c = 14.7094 (12) Å

β = 97.501 (1)°

V = 2710.7 (4) Å3

Z = 4

Mo Kα radiation

μ = 1.44 mm−1

T = 273 (2) K

0.34 × 0.21 × 0.07 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.641, T max = 0.906

8437 measured reflections

3090 independent reflections

2607 reflections with I > 2σ(I)

R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.024

wR(F 2) = 0.056

S = 1.03

3090 reflections

191 parameters

H-atom parameters constrained

Δρmax = 0.39 e Å−3

Δρmin = −0.18 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997 ▶); molecular graphics: SHELXTL ((Bruker, 2001 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536807065506/wm2168sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807065506/wm2168Isup2.hkl

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

[Ni2(C16H14N2O2)2]	F000 = 1344
Mr = 650.00	Dx = 1.593 Mg m−3
Monoclinic, C2/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 3127 reflections
a = 26.639 (2) Å	θ = 2.8–26.6º
b = 6.9775 (6) Å	µ = 1.44 mm−1
c = 14.7094 (12) Å	T = 273 (2) K
β = 97.501 (1)º	Block, brown
V = 2710.7 (4) Å3	0.34 × 0.21 × 0.07 mm
Z = 4

Bruker SMART CCD diffractometer	3090 independent reflections
Radiation source: fine-focus sealed tube	2607 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.023
T = 273(2) K	θmax = 27.5º
φ– and ω– scans	θmin = 2.8º
Absorption correction: multi-scan(SADABS; Bruker, 2001)	h = −34→32
Tmin = 0.641, Tmax = 0.906	k = −7→9
8437 measured reflections	l = −16→19

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.024	w = 1/[σ2(Fo2) + (0.0243P)2 + 0.8084P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.056	(Δ/σ)max < 0.001
S = 1.03	Δρmax = 0.39 e Å−3
3090 reflections	Δρmin = −0.18 e Å−3
191 parameters	Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.00018 (7)
Secondary atom site location: difference Fourier map

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	0.267171 (7)	0.20529 (3)	0.402119 (12)	0.02626 (7)
C1	0.13571 (6)	0.5214 (3)	0.42203 (12)	0.0431 (4)
H1	0.1505	0.6316	0.4492	0.052*
O1	0.21557 (4)	0.37606 (15)	0.43757 (7)	0.0331 (2)
C3	0.14245 (6)	0.1972 (2)	0.36791 (11)	0.0381 (4)
C2	0.16650 (6)	0.3629 (2)	0.40947 (10)	0.0333 (3)
C6	0.08435 (7)	0.5180 (3)	0.39534 (14)	0.0560 (5)
H6	0.0650	0.6253	0.4050	0.067*
C4	0.08991 (7)	0.1999 (3)	0.34122 (14)	0.0520 (5)
H4	0.0743	0.0914	0.3138	0.062*
C5	0.06105 (7)	0.3565 (3)	0.35422 (15)	0.0611 (6)
H5	0.0263	0.3551	0.3358	0.073*
C7	0.36315 (6)	0.3962 (2)	0.39857 (10)	0.0341 (4)
C12	0.38590 (6)	0.2332 (2)	0.36206 (12)	0.0383 (4)
C9	0.44526 (7)	0.5552 (3)	0.40933 (14)	0.0560 (5)
H9	0.4651	0.6624	0.4261	0.067*
C8	0.39502 (7)	0.5555 (3)	0.42134 (13)	0.0459 (4)
H8	0.3815	0.6644	0.4453	0.055*
C11	0.43741 (7)	0.2396 (3)	0.34965 (15)	0.0538 (5)
H11	0.4518	0.1331	0.3251	0.065*
N1	0.31197 (5)	0.03112 (18)	0.34648 (9)	0.0342 (3)
O2	0.31572 (4)	0.40839 (15)	0.41080 (8)	0.0386 (3)
N2	0.21745 (5)	0.00240 (18)	0.37265 (9)	0.0360 (3)
C13	0.35815 (6)	0.0617 (2)	0.33554 (11)	0.0392 (4)
H13	0.3750	−0.0349	0.3082	0.047*
C14	0.28630 (7)	−0.1438 (2)	0.30878 (12)	0.0430 (4)
H14A	0.3096	−0.2513	0.3158	0.052*
H14B	0.2747	−0.1270	0.2440	0.052*
C15	0.24182 (7)	−0.1823 (2)	0.35987 (13)	0.0443 (4)
H15A	0.2181	−0.2688	0.3250	0.053*
H15B	0.2532	−0.2407	0.4188	0.053*
C10	0.46695 (7)	0.3965 (3)	0.37237 (16)	0.0618 (6)
H10	0.5009	0.3974	0.3634	0.074*
C16	0.16935 (7)	0.0228 (2)	0.35544 (11)	0.0402 (4)
H16	0.1504	−0.0832	0.3332	0.048*

	U11	U22	U33	U12	U13	U23
Ni1	0.02833 (11)	0.02401 (11)	0.02671 (11)	0.00003 (8)	0.00461 (7)	−0.00381 (8)
C1	0.0403 (9)	0.0467 (10)	0.0431 (10)	0.0081 (8)	0.0082 (8)	0.0044 (8)
O1	0.0303 (6)	0.0334 (6)	0.0356 (6)	0.0004 (5)	0.0048 (4)	−0.0036 (5)
C3	0.0359 (9)	0.0435 (10)	0.0343 (9)	−0.0052 (7)	0.0030 (7)	0.0054 (7)
C2	0.0326 (8)	0.0405 (9)	0.0271 (8)	0.0013 (7)	0.0056 (6)	0.0068 (7)
C6	0.0404 (10)	0.0672 (14)	0.0615 (13)	0.0172 (10)	0.0112 (9)	0.0118 (11)
C4	0.0390 (10)	0.0646 (13)	0.0510 (12)	−0.0112 (9)	0.0007 (8)	0.0094 (10)
C5	0.0288 (9)	0.0842 (16)	0.0691 (14)	0.0010 (10)	0.0019 (9)	0.0164 (12)
C7	0.0328 (8)	0.0386 (9)	0.0309 (8)	−0.0011 (7)	0.0037 (7)	0.0026 (7)
C12	0.0357 (9)	0.0395 (9)	0.0403 (10)	0.0041 (7)	0.0066 (7)	0.0034 (7)
C9	0.0434 (11)	0.0600 (13)	0.0637 (13)	−0.0162 (9)	0.0043 (9)	0.0022 (10)
C8	0.0433 (10)	0.0445 (10)	0.0505 (11)	−0.0054 (8)	0.0082 (8)	−0.0047 (8)
C11	0.0390 (10)	0.0576 (12)	0.0667 (13)	0.0083 (9)	0.0143 (9)	0.0018 (10)
N1	0.0396 (7)	0.0309 (7)	0.0323 (7)	0.0024 (6)	0.0052 (6)	−0.0032 (6)
O2	0.0349 (6)	0.0327 (6)	0.0499 (7)	−0.0017 (5)	0.0119 (5)	−0.0051 (5)
N2	0.0425 (8)	0.0318 (7)	0.0342 (7)	−0.0048 (6)	0.0071 (6)	−0.0026 (6)
C13	0.0438 (10)	0.0365 (9)	0.0387 (9)	0.0109 (7)	0.0110 (7)	−0.0005 (7)
C14	0.0542 (11)	0.0333 (9)	0.0419 (10)	0.0018 (8)	0.0083 (8)	−0.0087 (7)
C15	0.0583 (12)	0.0301 (9)	0.0455 (10)	−0.0035 (8)	0.0102 (9)	−0.0035 (7)
C10	0.0330 (10)	0.0720 (14)	0.0817 (16)	−0.0024 (10)	0.0124 (10)	0.0065 (12)
C16	0.0447 (10)	0.0394 (9)	0.0361 (9)	−0.0142 (8)	0.0037 (7)	−0.0004 (7)

Ni1—O2	1.9115 (11)	C12—C13	1.433 (2)
Ni1—O1	1.9412 (10)	C9—C8	1.373 (3)
Ni1—N2	1.9484 (13)	C9—C10	1.392 (3)
Ni1—N1	1.9560 (13)	C9—H9	0.9300
C1—C6	1.373 (2)	C8—H8	0.9300
C1—C2	1.403 (2)	C11—C10	1.364 (3)
C1—H1	0.9300	C11—H11	0.9300
O1—C2	1.3217 (18)	N1—C13	1.279 (2)
C3—C4	1.403 (2)	N1—C14	1.472 (2)
C3—C2	1.421 (2)	N2—C16	1.281 (2)
C3—C16	1.436 (2)	N2—C15	1.466 (2)
C6—C5	1.387 (3)	C13—H13	0.9300
C6—H6	0.9300	C14—C15	1.508 (3)
C4—C5	1.364 (3)	C14—H14A	0.9700
C4—H4	0.9300	C14—H14B	0.9700
C5—H5	0.9300	C15—H15A	0.9700
C7—O2	1.3021 (18)	C15—H15B	0.9700
C7—C8	1.412 (2)	C10—H10	0.9300
C7—C12	1.426 (2)	C16—H16	0.9300
C12—C11	1.409 (2)
O2—Ni1—O1	91.35 (5)	C9—C8—C7	122.30 (18)
O2—Ni1—N2	171.05 (5)	C9—C8—H8	118.9
O1—Ni1—N2	91.21 (5)	C7—C8—H8	118.9
O2—Ni1—N1	92.53 (5)	C10—C11—C12	122.30 (19)
O1—Ni1—N1	170.36 (5)	C10—C11—H11	118.8
N2—Ni1—N1	83.67 (6)	C12—C11—H11	118.8
C6—C1—C2	121.78 (18)	C13—N1—C14	119.87 (14)
C6—C1—H1	119.1	C13—N1—Ni1	126.75 (11)
C2—C1—H1	119.1	C14—N1—Ni1	113.21 (10)
C2—O1—Ni1	125.41 (10)	C7—O2—Ni1	127.05 (10)
C4—C3—C2	119.15 (16)	C16—N2—C15	121.38 (14)
C4—C3—C16	118.13 (16)	C16—N2—Ni1	126.61 (12)
C2—C3—C16	122.67 (15)	C15—N2—Ni1	111.57 (11)
O1—C2—C1	118.39 (15)	N1—C13—C12	125.11 (15)
O1—C2—C3	124.28 (15)	N1—C13—H13	117.4
C1—C2—C3	117.33 (15)	C12—C13—H13	117.4
C1—C6—C5	120.74 (18)	N1—C14—C15	108.46 (14)
C1—C6—H6	119.6	N1—C14—H14A	110.0
C5—C6—H6	119.6	C15—C14—H14A	110.0
C5—C4—C3	122.08 (19)	N1—C14—H14B	110.0
C5—C4—H4	119.0	C15—C14—H14B	110.0
C3—C4—H4	119.0	H14A—C14—H14B	108.4
C4—C5—C6	118.93 (17)	N2—C15—C14	107.30 (13)
C4—C5—H5	120.5	N2—C15—H15A	110.3
C6—C5—H5	120.5	C14—C15—H15A	110.3
O2—C7—C8	118.69 (15)	N2—C15—H15B	110.3
O2—C7—C12	124.88 (15)	C14—C15—H15B	110.3
C8—C7—C12	116.43 (15)	H15A—C15—H15B	108.5
C11—C12—C7	119.51 (16)	C11—C10—C9	118.58 (18)
C11—C12—C13	117.88 (16)	C11—C10—H10	120.7
C7—C12—C13	122.60 (15)	C9—C10—H10	120.7
C8—C9—C10	120.87 (19)	N2—C16—C3	124.89 (15)
C8—C9—H9	119.6	N2—C16—H16	117.6
C10—C9—H9	119.6	C3—C16—H16	117.6
O2—Ni1—O1—C2	148.07 (12)	O1—Ni1—N1—C14	−54.8 (3)
N2—Ni1—O1—C2	−23.36 (12)	N2—Ni1—N1—C14	3.41 (11)
N1—Ni1—O1—C2	34.3 (4)	C8—C7—O2—Ni1	−170.58 (11)
Ni1—O1—C2—C1	−164.26 (11)	C12—C7—O2—Ni1	10.4 (2)
Ni1—O1—C2—C3	16.4 (2)	O1—Ni1—O2—C7	177.25 (13)
C6—C1—C2—O1	−179.44 (16)	N2—Ni1—O2—C7	−76.1 (4)
C6—C1—C2—C3	−0.1 (3)	N1—Ni1—O2—C7	−11.58 (13)
C4—C3—C2—O1	179.69 (15)	O2—Ni1—N2—C16	−86.3 (4)
C16—C3—C2—O1	2.5 (3)	O1—Ni1—N2—C16	20.29 (14)
C4—C3—C2—C1	0.4 (2)	N1—Ni1—N2—C16	−151.53 (15)
C16—C3—C2—C1	−176.84 (15)	O2—Ni1—N2—C15	86.0 (3)
C2—C1—C6—C5	−0.4 (3)	O1—Ni1—N2—C15	−167.35 (11)
C2—C3—C4—C5	−0.3 (3)	N1—Ni1—N2—C15	20.84 (11)
C16—C3—C4—C5	177.11 (18)	C14—N1—C13—C12	174.47 (15)
C3—C4—C5—C6	−0.2 (3)	Ni1—N1—C13—C12	−0.4 (2)
C1—C6—C5—C4	0.5 (3)	C11—C12—C13—N1	176.60 (17)
O2—C7—C12—C11	178.16 (16)	C7—C12—C13—N1	−4.5 (3)
C8—C7—C12—C11	−0.8 (2)	C13—N1—C14—C15	158.62 (15)
O2—C7—C12—C13	−0.7 (3)	Ni1—N1—C14—C15	−25.82 (17)
C8—C7—C12—C13	−179.72 (15)	C16—N2—C15—C14	133.16 (16)
C10—C9—C8—C7	1.0 (3)	Ni1—N2—C15—C14	−39.67 (16)
O2—C7—C8—C9	−179.08 (17)	N1—C14—C15—N2	41.36 (18)
C12—C7—C8—C9	0.0 (3)	C12—C11—C10—C9	0.2 (3)
C7—C12—C11—C10	0.8 (3)	C8—C9—C10—C11	−1.1 (3)
C13—C12—C11—C10	179.71 (19)	C15—N2—C16—C3	178.62 (15)
O2—Ni1—N1—C13	6.72 (14)	Ni1—N2—C16—C3	−9.7 (2)
O1—Ni1—N1—C13	120.4 (3)	C4—C3—C16—N2	176.60 (17)
N2—Ni1—N1—C13	178.60 (14)	C2—C3—C16—N2	−6.1 (3)
O2—Ni1—N1—C14	−168.47 (11)

Ni1—O2	1.9115 (11)
Ni1—O1	1.9412 (10)
Ni1—N2	1.9484 (13)
Ni1—N1	1.9560 (13)

O2—Ni1—O1	91.35 (5)
O2—Ni1—N2	171.05 (5)
O1—Ni1—N2	91.21 (5)
O2—Ni1—N1	92.53 (5)
O1—Ni1—N1	170.36 (5)
N2—Ni1—N1	83.67 (6)