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Acta Cryst. (2007). E63, m2424-m2425    [ doi:10.1107/S160053680704144X ]

Bis[[mu]2-N,N'-bis(2-oxidobenzyl)propane-1,3-diamine]-1[kappa]4O,N,N',O':2[kappa]2O,O';2[kappa]2O,O':3[kappa]4O,N,N',O'-bis(N,N'-dimethylformamide)-1[kappa]O,3[kappa]O-di-[mu]2-acetato-1:2[kappa]2O:O';2:3[kappa]2O:O'-dinickel(II)zinc(II)

L. Tatar Yildirim and Ü. Ergun

Abstract top

The molecule of the title compound, [Ni2Zn(C17H20N2O2)2(C2H3O2)2(C3H7NO)2], contains a linear hetero-trinuclear arrangement with a central ZnII ion located on an inversion centre. The Zn...Ni pairs are triply bridged via O atoms of SALPD2- [N,N'-bis(salicylidene)-1,3-propanediaminate] and acetate ligands. The central ZnII ion is in a distorted octahedral coordination environment formed by four O atoms of two SALPD2- ligands in the equatorial plane and two O atoms of two symmetry-related acetate ligands in the axial positions. The terminal NiII ions, related by an inversion centre, also have distorted octahedral coordination environments formed by two O and two N atoms of SALPD2- ligands in the equatorial plane; the axial positions are occupied by O atoms of dimethylformamide and acetate ligands, which are trans with respect to the terminal Ni atoms. The crystal structure is stabilized by weak intermolecular C-H...O hydrogen bonds.

Comment top

As it is well known, Schiff bases are easily reduced in alcoholic media with the presence of NaBH4 giving secondary amines. The ONNO phenol amines are obtained by the reduction of ONNO type Schiff bases (Aneetha et al., 1999; Reglinski et al., 2006). Bis-N,N'(2-salicylidene)-1,3-propanediamine is a Schiff base ligand tending to give polynuclear complexes [Fukuhara et al., 1990], and its reduction results in the formation of bis-N,N'(2-hydroxybenzyl) −1, 3-propanediamine. In its complexes, various combinations of metal ions in the central and terminal locations, as well as the µ-bridges, such as acetato, formato (CHO2), nitrato (NO3) or nitrito (NO2) anions are possible. Oxygen-bridged polynuclear complexes of transition series based on Schiff base ligands with similar formula have been the subject of much interest in our laboratory Ülkü et al., 1997; Tahir et al., 1998; Atakol et al., 1999;Ülkü et al., 1999;Ülkü et al., 2001; Arıcı et al., 2001; Tatar & Atakol, 2002; Tatar et al., 2007). The structure determination of the title compound, (I), a hetero-trinuclear [Zn{Ni(SALPD2−)(acetato)(dmf)}2] complex [where SALPD2− is N,N'-bis(salicylidene)-1, 3-propanediaminato and dmf is dimethylformamide], was undertaken in order to determine the ligands properties and also to compare the results obtained with those reported previously.

The molecule of the title compound, (I), contains a linear hetero-trinuclear arrangement with a central ZnII ion located on an inversion centre and two terminal NiII ions related by an inversion centre (Fig. 1). Four O atoms of two SALPD2− ligands in the equatorial plane and two O atoms of two acetate ligands located at the axial positions constitute the distorted octahedral coordination sphere around the Zn atom. The terminal NiII ions also have distorted octahedral coordination environments formed by two O and two N atoms of SALPD2− ligands in the equatorial plane. The Ni atom is 0.0548 (9) Å away from the equatorial plane. The dihedral angle between (O1/Ni/O2) and (N1/Ni/N2) planes is 4.22 (14)°. The axial positions are occupied by O atoms of dmf and acetato ligands, in which they are trans about the terminal Ni atoms. The dihedral angle between (O1/Zn/O2) and (O1/Ni/O2) planes is 19.44 (13)°. The overall result is three edge shared octahedrons, in which the closest Zn···Ni distance is 3.0702 (11) Å.

The coordination geometry about the central metal ion (Mc = Zn, Ni, Cu, Co) and the terminal metal ions (Mt = Ni, Zn, Cu) are very similar to those found for the corresponding complexes, in which the metal ions or type of µ-bridges are replaced. Mc ions of these complexes retain the distorted octahedral coordination. If there is a solvent molecule (e.g. dmf, DMSO: dimethylsulfoxide) in the coordination sphere of the terminal metal ion, its coordination will be six-coordinated polyhedron and the solvent molecule will be coordinated to the metal ion with longest coordination bond. If there is no solvent molecule in the coordination sphere of the terminal metal ion, its coordination will be five-coordinated polyhedron. A comparison of the properties of coordination bond length ranges (Mc—O and Mt—O/N), bond angle ranges (O—Mc—O and O/N—Mt—O/N) and Mc···Mt distances are given in Table 2, for the similar oxygen-bridged trinuclear complexes reported previously. The crystal structure may be stabilized by weak intermolecular C—H···O hydrogen bonds (Table 1).

Related literature top

For general backgroud, see: Aneetha et al. (1999); Reglinski et al. (2006); Fukuhara et al. (1990). For related literature, see: Ülkü et al. (1997); Tahir et al. (1998); Atakol et al. (1999); Ülkü et al. (1999); Ülkü et al. (2001); Arıcı et al. (2001); Tatar & Atakol (2002); Tatar et al. (2007).

Experimental top

The bis-N,N'(salicylidene)-1,3-propanedimine Schiff base was prepared through the condensation reaction of 1,3-propanediamine and salicylaldehyde in EtOH and it was reduced with NaBH4 in MeOH until the solution totally colorless. The phenolic amine ligand was precipitated with the addition of the excess of ice. The complex was prepared with template method, since it was very cumbersome to isolate mononuclear bis-N,N'(2-oxybenzyl)-1,3-propanediaminato -nickel(II) complex. Bis-N,N'(2-hydroxybenzyl)-1,3-propanediamine (568 mg, 2 mmol) was dissolved in hot dmf (50 ml). NiCl2·6H2O solution (475 mg, 2 mmol) in hot methanol (20 ml) and ET3N (0.5 ml) were added to it and the mixture was stirred for 10 min. Then, a solution of Zn(CH3COO)2·2H2O (220 mg, 1 mmol) in hot MeOH (10 ml) was added and the resulting mixture was kept on the bench for 2–3 d. The blue crystals were filtered off, and dried on air (yield; 440 mg, 44%).

Refinement top

H atoms were positioned geometrically, with N—H = 0.91 Å (for NH) and C—H = 0.93, 0.97 and 0.96 Å for aromatic, methylene and methyl H, and constrained to ride on their parent atoms, with Uiso(H) = xUeq(C,N), where x = 1.5 for methyl H, and x = 1.2 for all other H atoms.

Computing details top

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: CAD-4 EXPRESS (Enraf–Nonius, 1994); data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title molecule with the atom-numbering scheme. Displacement ellipsoids are drawn at the 25% probability level [symmetry code: (i) −x, −y, −z].
Bis[µ2-N,N'-bis(2-oxidobenzyl)propane-1,3-diamine]- 1κ4O,N,N',O':2κ2O,O'; 2κ2O,O':3κ4O,N,N',O'- bis(N,N'-dimethylformamide)-1κO,3κO-di-µ2– formato-1:2κ2O:O';2:3κ2O:O'- dinickel(II)zinc(II) top
Crystal data top
[Ni2Zn(C17H20N2O2)2(C2H3O2)2(C3H7NO)2]F000 = 1064
Mr = 1015.75Dx = 1.444 Mg m−3
Monoclinic, P21/nCu Kα radiation
λ = 1.54184 Å
Hall symbol: -P 2ynCell parameters from 15 reflections
a = 10.3035 (13) Åθ = 21.2–23.6º
b = 17.894 (4) ŵ = 2.06 mm−1
c = 12.584 (2) ÅT = 298 (2) K
β = 92.124 (13)ºNeedle, blue
V = 2318.5 (7) Å30.3 × 0.1 × 0.1 mm
Z = 2
Data collection top
Enraf–Nonius TurboCAD-4
diffractometer		Rint = 0.033
Radiation source: fine-focus sealed tubeθmax = 74.2º
Monochromator: graphiteθmin = 4.3º
non–profiled ω scansh = −12→0
Absorption correction: ψ scan
(North et al., 1968)		k = 0→22
Tmin = 0.781, Tmax = 0.814l = −15→15
4319 measured reflections3 standard reflections
4017 independent reflections every 120 min
2381 reflections with I > 2σ(I) intensity decay: 1%
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: geomt
R[F2 > 2σ(F2)] = 0.056H-atom parameters not refined
wR(F2) = 0.176  w = 1/[σ2(Fo2) + (0.0755P)2 + 2.4395P]
where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max < 0.001
4017 reflectionsΔρmax = 0.32 e Å−3
285 parametersΔρmin = −0.85 e Å−3
Primary atom site location: structure-invariant direct methodsExtinction coefficient: ?
Crystal data top
[Ni2Zn(C17H20N2O2)2(C2H3O2)2(C3H7NO)2]V = 2318.5 (7) Å3
Mr = 1015.75Z = 2
Monoclinic, P21/nCu Kα
a = 10.3035 (13) ŵ = 2.06 mm−1
b = 17.894 (4) ÅT = 298 (2) K
c = 12.584 (2) Å0.3 × 0.1 × 0.1 mm
β = 92.124 (13)º
Data collection top
Enraf–Nonius TurboCAD-4
diffractometer		2381 reflections with I > 2σ(I)
Absorption correction: ψ scan
(North et al., 1968)		Rint = 0.033
Tmin = 0.781, Tmax = 0.8143 standard reflections
4319 measured reflections every 120 min
4017 independent reflections intensity decay: 1%
Refinement top
R[F2 > 2σ(F2)] = 0.056285 parameters
wR(F2) = 0.176H-atom parameters not refined
S = 1.03Δρmax = 0.32 e Å−3
4017 reflectionsΔρmin = −0.85 e Å−3
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Zn0000.0520 (4)
Ni0.03300 (9)0.14110 (5)−0.13520 (7)0.0397 (3)
O10.0849 (4)0.0312 (2)−0.1398 (3)0.0419 (9)
O2−0.0889 (3)0.1023 (2)−0.0233 (3)0.0400 (9)
O30.1493 (4)0.0619 (2)0.0801 (3)0.0434 (10)
O40.1688 (4)0.1660 (2)−0.0187 (3)0.0469 (10)
O5−0.1190 (4)0.1291 (2)−0.2579 (3)0.0506 (11)
N10.1567 (5)0.1698 (3)−0.2571 (4)0.0488 (13)
H10.10660.173−0.3180.059*
N2−0.0410 (4)0.2498 (3)−0.1248 (4)0.0438 (12)
H2−0.09840.2555−0.18090.053*
N3−0.3129 (5)0.0750 (3)−0.2948 (4)0.0551 (14)
C10.1100 (5)−0.0014 (4)−0.2319 (5)0.0452 (14)
C20.0630 (6)−0.0711 (4)−0.2601 (6)0.0602 (18)
H2A0.0167−0.0984−0.21130.072*
C30.0832 (8)−0.1012 (5)−0.3592 (7)0.081 (3)
H30.0491−0.1478−0.37730.098*
C40.1544 (10)−0.0616 (6)−0.4316 (6)0.092 (3)
H40.1664−0.0805−0.49940.111*
C50.2067 (9)0.0058 (6)−0.4019 (6)0.087 (3)
H50.25710.0313−0.44980.104*
C60.1877 (6)0.0369 (4)−0.3051 (5)0.0560 (17)
C70.2506 (6)0.1092 (4)−0.2724 (6)0.064 (2)
H7A0.30090.1016−0.20660.077*
H7B0.31020.1242−0.32640.077*
C80.2227 (6)0.2431 (4)−0.2424 (5)0.0617 (19)
H8A0.27880.2516−0.30140.074*
H8B0.27690.2415−0.17770.074*
C90.1284 (6)0.3073 (4)−0.2357 (5)0.0598 (19)
H9A0.06560.3037−0.29480.072*
H9B0.17570.3537−0.24350.072*
C100.0561 (6)0.3104 (3)−0.1333 (5)0.0559 (17)
H10A0.11810.307−0.07370.067*
H10B0.01230.3582−0.1290.067*
C11−0.1156 (6)0.2582 (3)−0.0284 (5)0.0502 (16)
H11A−0.14560.3094−0.02360.06*
H11B−0.05920.24820.03330.06*
C12−0.2309 (5)0.2065 (3)−0.0269 (4)0.0417 (14)
C13−0.3568 (6)0.2341 (4)−0.0311 (5)0.0596 (18)
H13−0.37030.2853−0.0380.072*
C14−0.4622 (6)0.1873 (4)−0.0254 (6)0.065 (2)
H14−0.54610.2065−0.02970.078*
C15−0.4417 (6)0.1110 (4)−0.0130 (5)0.0599 (18)
H15−0.51250.0792−0.00750.072*
C16−0.3172 (6)0.0817 (4)−0.0088 (5)0.0505 (16)
H16−0.3050.03060.00120.061*
C17−0.2101 (5)0.1283 (3)−0.0194 (4)0.0402 (13)
C180.1879 (5)0.1269 (4)0.0641 (5)0.0441 (14)
C190.2672 (7)0.1630 (4)0.1520 (5)0.0622 (19)
H19A0.29140.21250.13090.093*
H19B0.34410.13390.16680.093*
H19C0.21710.16580.21470.093*
C20−0.1918 (6)0.0743 (4)−0.2577 (5)0.0530 (17)
H20−0.15910.0298−0.22960.064*
C21−0.3956 (9)0.0099 (5)−0.2891 (8)0.105 (3)
H21A−0.480.0215−0.31960.158*
H21B−0.4035−0.0044−0.21610.158*
H21C−0.3583−0.0305−0.32780.158*
C22−0.3717 (7)0.1418 (4)−0.3325 (7)0.093 (3)
H22A−0.45980.1317−0.35580.14*
H22B−0.32440.1608−0.3910.14*
H22C−0.37090.1781−0.27640.14*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Zn0.0468 (7)0.0557 (8)0.0534 (7)−0.0001 (6)0.0004 (5)0.0038 (6)
Ni0.0329 (5)0.0467 (6)0.0395 (5)−0.0020 (4)0.0006 (4)0.0042 (5)
O10.039 (2)0.046 (2)0.041 (2)−0.0007 (18)0.0041 (17)−0.0011 (18)
O20.033 (2)0.043 (2)0.044 (2)0.0033 (17)0.0021 (17)0.0048 (18)
O30.043 (2)0.040 (2)0.047 (2)−0.0032 (19)−0.0082 (18)0.0009 (19)
O40.042 (2)0.053 (3)0.046 (2)−0.0076 (19)−0.0054 (18)0.009 (2)
O50.044 (2)0.060 (3)0.047 (2)−0.007 (2)−0.0066 (19)0.005 (2)
N10.040 (3)0.068 (3)0.039 (3)−0.003 (3)0.001 (2)0.010 (3)
N20.040 (3)0.047 (3)0.044 (3)−0.004 (2)−0.002 (2)0.006 (2)
N30.044 (3)0.059 (4)0.061 (3)−0.006 (3)−0.017 (3)0.013 (3)
C10.035 (3)0.054 (4)0.046 (3)0.011 (3)0.000 (3)−0.007 (3)
C20.047 (4)0.070 (5)0.064 (4)0.009 (3)0.003 (3)−0.025 (4)
C30.065 (5)0.089 (6)0.089 (6)0.025 (5)−0.011 (5)−0.039 (5)
C40.106 (7)0.121 (8)0.050 (5)0.041 (7)0.012 (5)−0.021 (5)
C50.092 (6)0.110 (8)0.060 (5)0.023 (6)0.024 (4)0.002 (5)
C60.046 (4)0.078 (5)0.044 (4)0.019 (4)0.008 (3)0.004 (3)
C70.045 (4)0.083 (5)0.065 (5)0.004 (4)0.020 (3)0.024 (4)
C80.047 (4)0.079 (5)0.058 (4)−0.016 (4)−0.001 (3)0.022 (4)
C90.053 (4)0.070 (5)0.057 (4)−0.017 (4)−0.004 (3)0.019 (4)
C100.057 (4)0.044 (4)0.065 (4)−0.011 (3)−0.008 (3)0.005 (3)
C110.054 (4)0.043 (4)0.053 (4)0.005 (3)−0.003 (3)−0.001 (3)
C120.035 (3)0.047 (4)0.043 (3)0.007 (3)0.002 (3)0.003 (3)
C130.052 (4)0.063 (5)0.065 (4)0.017 (3)0.010 (3)0.012 (4)
C140.038 (4)0.090 (6)0.068 (5)0.016 (4)0.007 (3)0.006 (4)
C150.035 (3)0.078 (5)0.068 (5)−0.003 (3)0.011 (3)−0.005 (4)
C160.035 (3)0.053 (4)0.064 (4)−0.002 (3)0.008 (3)−0.003 (3)
C170.032 (3)0.053 (4)0.036 (3)0.003 (3)0.005 (2)0.000 (3)
C180.032 (3)0.054 (4)0.047 (3)0.003 (3)−0.002 (2)−0.003 (3)
C190.067 (5)0.060 (4)0.058 (4)−0.014 (4)−0.013 (4)0.001 (3)
C200.046 (4)0.063 (4)0.049 (4)0.012 (3)−0.015 (3)0.006 (3)
C210.087 (6)0.088 (6)0.137−0.028 (5)−0.043 (6)0.025 (6)
C220.057 (5)0.084 (6)0.137 (8)−0.003 (5)−0.017 (5)0.036 (6)
Geometric parameters (Å, °) top
Zn—O1i2.070 (4)C5—H50.93
Zn—O12.070 (4)C6—C71.497 (9)
Zn—O22.064 (4)C7—H7A0.97
Zn—O2i2.064 (4)C7—H7B0.97
Zn—O3i2.121 (4)C8—C91.510 (9)
Zn—O32.121 (4)C8—H8A0.97
Zn—Nii3.0705 (11)C8—H8B0.97
Zn—Ni3.0705 (11)C9—C101.513 (9)
Ni—O12.039 (4)C9—H9A0.97
Ni—O22.043 (4)C9—H9B0.97
Ni—O42.038 (4)C10—H10A0.97
Ni—O52.168 (4)C10—H10B0.97
Ni—N12.094 (5)C11—H11A0.97
Ni—N22.095 (5)C11—H11B0.97
O1—C11.331 (7)C12—C111.505 (8)
O2—C171.334 (6)C12—C131.387 (8)
O3—C181.248 (7)C13—C141.375 (9)
O4—C181.264 (7)C13—H130.93
O5—C201.234 (7)C14—H140.93
N1—C71.470 (8)C15—C141.389 (9)
N1—C81.486 (8)C15—H150.93
N1—H10.91C16—C151.386 (8)
N2—C101.482 (7)C16—H160.93
N2—C111.468 (7)C17—C161.394 (8)
N2—H20.91C17—C121.420 (8)
N3—C201.316 (7)C18—C191.498 (8)
N3—C211.446 (9)C19—H19A0.96
N3—C221.414 (8)C19—H19B0.96
C1—C21.380 (8)C19—H19C0.96
C1—C61.419 (9)C20—H200.93
C2—C31.382 (9)C21—H21A0.96
C2—H2A0.93C21—H21B0.96
C3—C41.386 (12)C21—H21C0.96
C3—H30.93C22—H22A0.96
C4—H40.93C22—H22B0.96
C5—C41.367 (12)C22—H22C0.96
C5—C61.361 (10)
O2—Zn—O2i180.0 (3)C4—C5—H5118.7
O2—Zn—O1i99.24 (15)N2—C11—C12112.7 (5)
O2i—Zn—O1i80.76 (15)N2—C11—H11A109.1
O2—Zn—O180.76 (15)C12—C11—H11A109.1
O2i—Zn—O199.24 (15)N2—C11—H11B109.1
O1i—Zn—O1180.0 (3)C12—C11—H11B109.1
O2—Zn—O3i94.90 (15)H11A—C11—H11B107.8
O2i—Zn—O3i85.10 (15)N1—C8—C9112.7 (5)
O1i—Zn—O3i86.64 (14)N1—C8—H8A109
O1—Zn—O3i93.36 (14)C9—C8—H8A109
O2—Zn—O385.10 (15)N1—C8—H8B109
O2i—Zn—O394.90 (15)C9—C8—H8B109
O1i—Zn—O393.36 (14)H8A—C8—H8B107.8
O1—Zn—O386.64 (14)C8—C9—C10114.4 (5)
O3i—Zn—O3180.0 (3)C8—C9—H9A108.7
O2—Zn—Nii138.64 (10)C10—C9—H9A108.7
O2i—Zn—Nii41.36 (10)C8—C9—H9B108.7
O1i—Zn—Nii41.27 (11)C10—C9—H9B108.7
O1—Zn—Nii138.73 (11)H9A—C9—H9B107.6
O3i—Zn—Nii74.97 (10)C5—C6—C1119.1 (8)
O3—Zn—Nii105.03 (10)C5—C6—C7121.7 (7)
O2—Zn—Ni41.36 (10)C1—C6—C7119.2 (6)
O2i—Zn—Ni138.64 (10)N1—C7—C6113.1 (5)
O1i—Zn—Ni138.73 (11)N1—C7—H7A109
O1—Zn—Ni41.27 (11)C6—C7—H7A109
O3i—Zn—Ni105.03 (10)N1—C7—H7B109
O3—Zn—Ni74.97 (10)C6—C7—H7B109
Nii—Zn—Ni180.00 (3)H7A—C7—H7B107.8
O4—Ni—O193.30 (16)C18—O4—Ni123.6 (4)
O4—Ni—O290.10 (15)C18—O3—Zn129.8 (4)
O1—Ni—O281.99 (15)C20—N3—C22121.0 (6)
O4—Ni—N193.04 (18)C20—N3—C21121.9 (6)
O1—Ni—N192.76 (18)C22—N3—C21116.8 (6)
O2—Ni—N1174.03 (18)O3—C18—O4127.5 (6)
O4—Ni—N289.64 (18)O3—C18—C19116.8 (5)
O1—Ni—N2173.45 (17)O4—C18—C19115.8 (6)
O2—Ni—N292.17 (17)C16—C15—C14120.9 (6)
N1—Ni—N292.9 (2)C16—C15—H15119.5
O4—Ni—O5172.84 (17)C14—C15—H15119.5
O1—Ni—O593.85 (16)O5—C20—N3124.2 (6)
O2—Ni—O590.62 (15)O5—C20—H20117.9
N1—Ni—O586.90 (17)N3—C20—H20117.9
N2—Ni—O583.21 (17)C14—C13—C12121.4 (7)
O4—Ni—Zn82.44 (11)C14—C13—H13119.3
O1—Ni—Zn42.04 (10)C12—C13—H13119.3
O2—Ni—Zn41.86 (10)N2—C10—C9112.9 (5)
N1—Ni—Zn133.64 (15)N2—C10—H10A109
N2—Ni—Zn132.91 (14)C9—C10—H10A109
O5—Ni—Zn102.77 (12)N2—C10—H10B109
C20—O5—Ni120.1 (4)C9—C10—H10B109
C17—O2—Ni120.5 (3)H10A—C10—H10B107.8
C17—O2—Zn135.6 (4)C1—C2—C3121.4 (7)
Ni—O2—Zn96.77 (15)C1—C2—H2A119.3
C1—O1—Ni120.4 (4)C3—C2—H2A119.3
C1—O1—Zn136.4 (4)N3—C22—H22A109.5
Ni—O1—Zn96.69 (16)N3—C22—H22B109.5
C7—N1—C8111.5 (5)H22A—C22—H22B109.5
C7—N1—Ni109.7 (4)N3—C22—H22C109.5
C8—N1—Ni114.4 (4)H22A—C22—H22C109.5
C7—N1—H1106.9H22B—C22—H22C109.5
C8—N1—H1106.9C13—C14—C15119.1 (6)
Ni—N1—H1106.9C13—C14—H14120.4
C11—N2—C10111.1 (5)C15—C14—H14120.4
C11—N2—Ni110.5 (3)C2—C3—C4119.7 (8)
C10—N2—Ni115.3 (4)C2—C3—H3120.1
C11—N2—H2106.5C4—C3—H3120.1
C10—N2—H2106.5N3—C21—H21A109.5
Ni—N2—H2106.5N3—C21—H21B109.5
O2—C17—C16122.7 (5)H21A—C21—H21B109.5
O2—C17—C12118.7 (5)N3—C21—H21C109.5
C16—C17—C12118.6 (5)H21A—C21—H21C109.5
O1—C1—C2122.8 (6)H21B—C21—H21C109.5
O1—C1—C6119.1 (6)C5—C4—C3119.0 (8)
C2—C1—C6118.1 (6)C5—C4—H4120.5
C13—C12—C17119.5 (6)C3—C4—H4120.5
C13—C12—C11121.2 (6)C18—C19—H19A109.5
C17—C12—C11119.3 (5)C18—C19—H19B109.5
C15—C16—C17120.3 (6)H19A—C19—H19B109.5
C15—C16—H16119.8C18—C19—H19C109.5
C17—C16—H16119.8H19A—C19—H19C109.5
C6—C5—C4122.5 (9)H19B—C19—H19C109.5
C6—C5—H5118.7
O2—Zn—Ni—O498.7 (2)N2—Ni—N1—C7167.5 (4)
O2i—Zn—Ni—O4−81.3 (2)O5—Ni—N1—C7−109.4 (4)
O1i—Zn—Ni—O476.47 (19)Zn—Ni—N1—C7−4.7 (5)
O1—Zn—Ni—O4−103.53 (19)O4—Ni—N1—C8−48.4 (4)
O3i—Zn—Ni—O4178.82 (16)O1—Ni—N1—C8−141.9 (4)
O3—Zn—Ni—O4−1.18 (16)N2—Ni—N1—C841.4 (4)
O2—Zn—Ni—O1−157.8 (2)O5—Ni—N1—C8124.4 (4)
O2i—Zn—Ni—O122.2 (2)Zn—Ni—N1—C8−130.9 (4)
O1i—Zn—Ni—O1180O4—Ni—N2—C11−74.7 (4)
O3i—Zn—Ni—O1−77.64 (19)O2—Ni—N2—C1115.4 (4)
O3—Zn—Ni—O1102.36 (19)N1—Ni—N2—C11−167.7 (4)
O2i—Zn—Ni—O2180O5—Ni—N2—C11105.8 (4)
O1i—Zn—Ni—O2−22.2 (2)Zn—Ni—N2—C114.6 (5)
O1—Zn—Ni—O2157.8 (2)O4—Ni—N2—C1052.3 (4)
O3i—Zn—Ni—O280.15 (19)O2—Ni—N2—C10142.4 (4)
O3—Zn—Ni—O2−99.85 (19)N1—Ni—N2—C10−40.7 (4)
O2—Zn—Ni—N1−174.3 (2)O5—Ni—N2—C10−127.2 (4)
O2i—Zn—Ni—N15.7 (2)Zn—Ni—N2—C10131.7 (4)
O1i—Zn—Ni—N1163.4 (2)Ni—O2—C17—C16134.1 (5)
O1—Zn—Ni—N1−16.6 (2)Zn—O2—C17—C16−8.7 (8)
O3i—Zn—Ni—N1−94.2 (2)Ni—O2—C17—C12−45.6 (6)
O3—Zn—Ni—N185.8 (2)Zn—O2—C17—C12171.6 (4)
O2—Zn—Ni—N216.3 (2)Ni—O1—C1—C2−135.3 (5)
O2i—Zn—Ni—N2−163.7 (2)Zn—O1—C1—C29.0 (9)
O1i—Zn—Ni—N2−5.9 (2)Ni—O1—C1—C644.3 (7)
O1—Zn—Ni—N2174.1 (2)Zn—O1—C1—C6−171.4 (4)
O3i—Zn—Ni—N296.4 (2)O2—C17—C12—C13175.2 (5)
O3—Zn—Ni—N2−83.6 (2)C16—C17—C12—C13−4.5 (8)
O2—Zn—Ni—O5−76.33 (19)O2—C17—C12—C11−5.8 (8)
O2i—Zn—Ni—O5103.67 (19)C16—C17—C12—C11174.5 (5)
O1i—Zn—Ni—O5−98.5 (2)O2—C17—C16—C15−175.2 (6)
O1—Zn—Ni—O581.5 (2)C12—C17—C16—C154.4 (9)
O3i—Zn—Ni—O53.82 (16)C10—N2—C11—C12169.4 (5)
O3—Zn—Ni—O5−176.18 (16)Ni—N2—C11—C12−61.3 (5)
O1—Ni—O5—C2042.3 (5)C13—C12—C11—N2−114.2 (6)
O2—Ni—O5—C20−39.7 (5)C17—C12—C11—N266.8 (7)
N1—Ni—O5—C20134.8 (5)C7—N1—C8—C9175.1 (5)
N2—Ni—O5—C20−131.8 (5)Ni—N1—C8—C9−59.6 (6)
Zn—Ni—O5—C200.7 (5)N1—C8—C9—C1072.0 (7)
O4—Ni—O2—C17126.7 (4)C4—C5—C6—C1−0.5 (12)
O1—Ni—O2—C17−140.0 (4)C4—C5—C6—C7177.3 (8)
N2—Ni—O2—C1737.0 (4)O1—C1—C6—C5−175.9 (6)
O5—Ni—O2—C17−46.2 (4)C2—C1—C6—C53.7 (9)
Zn—Ni—O2—C17−154.8 (5)O1—C1—C6—C76.3 (9)
O4—Ni—O2—Zn−78.51 (17)C2—C1—C6—C7−174.1 (6)
O1—Ni—O2—Zn14.81 (15)C8—N1—C7—C6−170.6 (5)
N2—Ni—O2—Zn−168.16 (17)Ni—N1—C7—C661.6 (6)
O5—Ni—O2—Zn108.61 (16)C5—C6—C7—N1115.0 (7)
O1i—Zn—O2—C17−46.3 (5)C1—C6—C7—N1−67.2 (8)
O1—Zn—O2—C17133.7 (5)O1—Ni—O4—C18−46.3 (5)
O3i—Zn—O2—C1741.1 (5)O2—Ni—O4—C1835.7 (5)
O3—Zn—O2—C17−138.9 (5)N1—Ni—O4—C18−139.2 (5)
Nii—Zn—O2—C17−31.6 (6)N2—Ni—O4—C18127.9 (5)
Ni—Zn—O2—C17148.4 (6)Zn—Ni—O4—C18−5.6 (4)
O1i—Zn—O2—Ni165.37 (14)O2—Zn—O3—C18−31.5 (5)
O1—Zn—O2—Ni−14.63 (14)O2i—Zn—O3—C18148.5 (5)
O3i—Zn—O2—Ni−107.25 (16)O1i—Zn—O3—C18−130.5 (5)
O3—Zn—O2—Ni72.75 (16)O1—Zn—O3—C1849.5 (5)
Nii—Zn—O2—Ni180Nii—Zn—O3—C18−170.7 (5)
O4—Ni—O1—C1−129.0 (4)Ni—Zn—O3—C189.3 (5)
O2—Ni—O1—C1141.3 (4)Zn—O3—C18—O4−18.1 (9)
N1—Ni—O1—C1−35.8 (4)Zn—O3—C18—C19162.7 (4)
O5—Ni—O1—C151.2 (4)Ni—O4—C18—O315.1 (9)
Zn—Ni—O1—C1156.1 (5)Ni—O4—C18—C19−165.7 (4)
O4—Ni—O1—Zn74.88 (16)C17—C16—C15—C14−1.5 (10)
O2—Ni—O1—Zn−14.76 (14)Ni—O5—C20—N3150.1 (5)
N1—Ni—O1—Zn168.08 (17)C22—N3—C20—O5−4.1 (11)
O5—Ni—O1—Zn−104.84 (16)C21—N3—C20—O5−177.7 (7)
O2—Zn—O1—C1−134.9 (5)C17—C12—C13—C141.7 (10)
O2i—Zn—O1—C145.1 (5)C11—C12—C13—C14−177.3 (6)
O3i—Zn—O1—C1−40.5 (5)C11—N2—C10—C9−175.7 (5)
O3—Zn—O1—C1139.5 (5)Ni—N2—C10—C957.6 (6)
Nii—Zn—O1—C130.5 (6)C8—C9—C10—N2−70.7 (7)
Ni—Zn—O1—C1−149.5 (6)O1—C1—C2—C3175.4 (6)
O2—Zn—O1—Ni14.66 (14)C6—C1—C2—C3−4.2 (9)
O2i—Zn—O1—Ni−165.34 (14)C12—C13—C14—C151.2 (11)
O3i—Zn—O1—Ni109.08 (16)C16—C15—C14—C13−1.4 (11)
O3—Zn—O1—Ni−70.92 (16)C1—C2—C3—C41.4 (11)
Nii—Zn—O1—Ni180C6—C5—C4—C3−2.4 (14)
O4—Ni—N1—C777.7 (4)C2—C3—C4—C52.0 (13)
O1—Ni—N1—C7−15.7 (4)
Symmetry codes: (i) −x, −y, −z.
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C2—H2A···O3ii0.932.513.211 (7)133
C16—H16···O3ii0.932.553.241 (8)132
C20—H20···O3ii0.932.503.325 (8)149
Symmetry codes: (ii) −x, −y, −z.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C2—H2A···O3i0.932.513.211 (7)133
C16—H16···O3i0.932.553.241 (8)132
C20—H20···O3i0.932.503.325 (8)149
Symmetry codes: (i) −x, −y, −z.
Table 2
? top
ComplexMc···MtMc-OO-Mc-OMt-O/NO/N-Mt-O/N
(I)3.0705 (11)2.064 (4)80.76 (15)2.038 (4)81.99 (15)
2.121 (4)99.24 (15)2.168 (4)93.85 (16)
(II)3.0520 (8)2.098 (3)77.5 (1)1.975 (4)80.3 (1)
2.124 (4)102.5 (1)2.071 (4)104.9 (2)
(III)3.0017 (6)2.055 (2)76.04 (9)1.941 (2)81.5 (1)
2.188 (2)93.74 (9)2.355 (3)97.0 (1)
(IV)Not_given2.083 (6)79.0 (2)1.995 (5)82.1 (2)
2.118 (5)84.5 (2)2.179 (6)97.8 (3)
(V)3.043 (2)2.024 (3)79.4 (1)2.010 (3)79.4 (1)
2.098 (3)87.1 (1)2.254 (3)96.2 (2)
(VI)2.9967 (4)2.048 (2)78.70 (8)2.003 (2)80.88 (8)
2.103 (2)85.86 (9)2.152 (2)98.5 (1)
(VII)3.0556 (5)2.0705 (19)78.89 (8)2.0082 (19)81.65 (8)
2.082 (2)92.92 (8)2.186 (2)97.95 (10)
(VIII)3.0601 (6)2.052 (2)80.96 (9)2.029 (2)81.79 (9)
2.102 (2)86.57 (9)2.165 (2)96.95 (10)
(IX)3.0857 (14)2.075 (3)80.34 (12)2.037 (3)81.85 (12)
2.160 (3)99.66 (12)2.147 (3)93.54 (13)
Notes: (II) [Zn{Zn(SALPD2−)(acetato)}2] (Ülkü et al., 2001); (III) [Zn{Cu(SALPD2−)(nitrato)}2] (Ülkü et al., 1999); (IV) [Co{Ni(SALPD2−)(nitrito) (DMF)}2] (Atakol et al., 1999); (V) [Ni{Ni(SALPD2−)(acetato)(DMSO)}2] (Ülkü et al., 1997); (VI) [Cu{Ni(SALPD2−)(nitrito)(DMF)}2] (Tahir et al., 1998); (VII) [Cu{Ni(SALPD2−)(acetato)(DMF)}2] (Arıcı et al., 2001); (VIII) [Ni{Ni(SALPD2−)(acetato)(DMF)}2] (Tatar & Atakol, 2002); (IX) [Ni{Ni(DMLH2)(formato)(DMF)}2], where DMLH2 = (C19H24N2O2) (Tatar et al., 2007).
Acknowledgements top

Partial support of this work by Hacettepe University Scientific Research Unit (grant No. 04 A602004) is gratefully acknowledged.

references
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