Di-μ2-acetato-1:2κ2O:O′;2:3κ2O:O′-bis­(N,N′-dimethyl­formamide)-1κO,3κO-bis­{μ2-2,2′-[propane-1,3-diylbis(imino­methyl­ene)]diphenolato-1κ4O,N,N′,O′:2κ2O,O′;2κ2O,O′:3κ4O,N,N′,O′-1,3-dinickel(II)-2-cadmium(II)

Tatar Yıldırım, L.; Atakol, O.

doi:10.1107/S1600536807067724

metal-organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 64| Part 2| February 2008| Pages m291-m292

doi:10.1107/S1600536807067724

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Di-μ₂-acetato-1:2κ²O:O′;2:3κ²O:O′-bis(N,N′-dimethylformamide)-1κO,3κO-bis{μ₂-2,2′-[propane-1,3-diylbis(iminomethylene)]diphenolato-1κ⁴O,N,N′,O′:2κ²O,O′;2κ²O,O′:3κ⁴O,N,N′,O′-1,3-dinickel(II)-2-cadmium(II)

Leyla Tatar Yıldırım ^a ^* and Orhan Atakol ^b

^aDepartment of Physics Engineering, Hacettepe University, 06800 Beytepe, Ankara, Turkey, and ^bDepartment of Chemistry, Ankara University, Ankara, Turkey
^*Correspondence e-mail: tatar@hacettepe.edu.tr

(Received 4 December 2007; accepted 19 December 2007; online 4 January 2008)

The crystal structure of the title compound, [Ni₂Cd(C₁₇H₁₆N₂O₂)₂(C₂H₃O₂)₂(C₃H₇NO)₂], contains discrete centrosymmetric hetero-trinuclear molecules in which Ni/Cd atom pairs are triply bridged via O atoms from the SALPD²⁻ [N,N′-bis(salicylidene)-1,3-propanediaminate] and acetate ligands. The central Cd^II ion is in a distorted octahedral coordination environment formed by four O atoms from two SALPD²⁻ ligands in the equatorial plane and two O atoms of two symmetry-related acetate ligands in the axial positions. The symmetry-related Ni^II ions are in slightly distorted octahedral environments, coordinated by two O and two N atoms from tetradendate SALPD²⁻ ligands in the equatorial plane, while the axial positions are occupied by O atoms from a dimethylformamide and an acetate ligand. This results in the formation of three edge-shared octahedra in which the Ni⋯Cd distance is 3.1482 (15) Å. The crystal structure is stabilized by weak C—H⋯O hydrogen bonds.

Related literature

For general background, see: Aneetha et al. (1999); Reglinski et al. (2006 ); Fukuhara et al. (1990 ); Barandika et al. (1999 ). For related literature, see: Aneetha et al. (1999 ); Atakol et al. (1999 );Ülkü et al. (1999 ); Ülkü et al. (2001 ); Tatar & Atakol (2002 ); Tatar Yıldırım et al. (2007 ); Tatar Yıldırım & Ergün (2007 ).

Experimental

Crystal data

[Ni₂Cd(C₁₇H₁₆N₂O₂)₂(C₂H₃O₂)₂(C₃H₇NO)₂]
M_r = 1062.77
Monoclinic, P 2₁ /n
a = 10.285 (3) Å
b = 18.040 (5) Å
c = 12.590 (3) Å
β = 92.12 (2)°
V = 2334.4 (11) Å³
Z = 2
Mo Kα radiation
μ = 1.31 mm⁻¹
T = 295 (2) K
0.4 × 0.1 × 0.1 mm

Data collection

Enraf–Nonius TurboCAD-4 diffractometer
Absorption correction: ψ scan (North et al., 1968 ) T_min = 0.854, T_max = 0.877
3960 measured reflections
3612 independent reflections
1997 reflections with I > 2σ(I)
R_int = 0.076
3 standard reflections frequency: 120 min intensity decay: 1%

Refinement

R[F² > 2σ(F²)] = 0.071
wR(F²) = 0.239
S = 1.02
3612 reflections
287 parameters
H-atom parameters not refined
Δρ_max = 0.88 e Å⁻³
Δρ_min = −1.51 e Å⁻³

Table 1
Selected bond lengths (Å)

Cd—O1	2.157 (7)
Cd—O2	2.151 (7)
Cd—O3	2.212 (7)
Ni—N1	2.094 (9)
Ni—N2	2.101 (9)
Ni—O1	2.031 (8)
Ni—O2	2.060 (7)
Ni—O4	2.045 (7)
Ni—O5	2.180 (7)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯O3ⁱ	0.93	2.56	3.308 (16)	138
C20—H20⋯O3ⁱ	0.93	2.59	3.409 (14)	147
Symmetry code: (i) -x, -y, -z.

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994 ); cell refinement: CAD-4 EXPRESS; 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 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536807067724/lh2581sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536807067724/lh2581Isup2.hkl

checkCIF report

Comment top

Recently, ONNO phenol amines have been reported 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 ligand which tends to give polynuclear complexes. Reduction of this Schiff base results in the formation of bis-N,N'(2-hydroxybenzyl)-1, 3-propanediamine. The ONNO type ligand stereochemistry around metal ions and the structure of the O-atom bridges influence the magnetic exchange interactions (Barandika et al., 1999; Fukuhara et al., 1990).

This study deals with the investigation of the production of hetero-trinuclear complexes with the use of bis-N,N'(2-hydroxybenzyl)-1,3-propanediamine and it was observed that Ni(II)—Cd(II)—Ni(II) type complexes were formed. The crystal structure of the title compound (I), contains a linear Ni—Cd—Ni trinuclear complex with a central Cd^II ion located on an inversion centre and terminal Ni^II ions related by this inversion centre (Fig. 1). The Cd^II ion has a distorted octahedral coordination environment, formed by four O atoms from two SALPD^2- ligands in the equatorial plane and two O atoms from two acetate ligands at the axial positions. The coordination bond lengths and angles around the Cd^II ion range between 2.151 (7) - 2.212 (7)Å and 78.4 (3) - 101.6 (3)°, respectively.

The terminal Ni^II ions have slightly distorted octahedral coordination environments formed by two O atoms and two N atoms from SALPD^2- ligands in the equatorial plane and two O atoms from acetate ligand and dimethylformamide ligand at the axial positions. In the Ni coordination sphere bond lengths and angles range between 2.031 (8) - 2.180 (7)Å and 83.3 (3) - 93.8 (3)°, respectively.

The overall result is three edge-shared octahedral in which the closest Ni···Cd distance is 3.1482 (15) Å. The crystal structure is stabilized by weak C—H···O hydrogen bonds.

The coordination geometry of the metal ions is very similar to those found for the corresponding complexes reported previously (Tatar & Ergün, 2007; Tatar & Atakol et al., 2007; Tatar & Atakol 2002; Atakol et al., 1999;Ülkü et al., 1999;Ülkü et al., 2001).

Related literature top

For general backgroud, see: Aneetha et al. 1(999); Reglinski et al. (2006); Fukuhara et al. (1990); Barandika et al. (1999). For related literature, see: Aneetha et al. (1999); Atakol et al. (1999);Ülkü et al. (1999); Ülkü et al. (2001); Tatar & Atakol (2002); Tatar Yıldırım et al. (2007); Tatar Yıldırım & Ergün (2007).

Experimental top

The related Schiff Base, bis-N,N'(salicylidene)-1,3-propanedimine was prepared through the condensation reaction of an 1,3-propanediamine and salicylaldehyde in EtOH and this Schiff bases prepared was reduced with NaBH₄ in MeOH until the solution was completely colorless. The Phenolic amine ligand was precipitated with the addition of excess 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. 0.568 g (0.002 mole) bis-N,N'(2-hydroxybenzyl)-1,3-propanediamine was dissolved in 50 ml hot DMF. 0.475 g(0.002 mole) NiCl₂.6H₂O solution in 20 ml hot methanol and 0.5 ml Et₃N were added to it and the mixture was stirred for ten minutes. Then a solution of 0.312 g (0.001 mol) Cd(CH₃COO)₂.4H₂O in 20 ml hot methanol was added and the resulting mixture was kept on the bench for 3–4 days. The blue crystals were filtered off and dried in air.

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

Fig. 1. The molecular structure of the title molecule with the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level (symmetry code (i): -x, -y, -z). H atoms bonded to C atoms are not shown.

Di-µ₂-acetato-1:2κ²O:O';2:3κ²O:O'-bis(N,N'-dimethylformamide)- 1κO,3κO-bis{µ₂-2,2'-[propane-1,3-diylbis(iminomethylene)]diphenolato- 1κ⁴O,N,N',O':2κ²O,O';2κ²O,O':3κ⁴O,N,N',O'-1,3-dinickel(II)- 2-cadmium(II) top

Crystal data top

[Ni₂Cd(C₁₇H₁₆N₂O₂)₂(C₂H₃O₂)₂(C₃H₇NO)₂]	F(000) = 1100
M_r = 1062.77	D_x = 1.512 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 15 reflections
a = 10.285 (3) Å	θ = 10.0–11.1°
b = 18.040 (5) Å	µ = 1.31 mm⁻¹
c = 12.590 (3) Å	T = 295 K
β = 92.12 (2)°	Prism, blue
V = 2334.4 (11) Å³	0.4 × 0.1 × 0.1 mm
Z = 2

Data collection top

Enraf–Nonius TurboCAD-4 diffractometer	R_int = 0.076
non–profiled ω scans	θ_max = 25.1°, θ_min = 2.5°
Absorption correction: ψ scan (North et al., 1968)	h = 0→12
T_min = 0.854, T_max = 0.877	k = 0→21
3960 measured reflections	l = −14→12
3612 independent reflections	3 standard reflections every 120 min
1997 reflections with I > 2σ(I)	intensity decay: 1%

Refinement top

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)] = 0.072	Hydrogen site location: geomtr
wR(F²) = 0.239	H-atom parameters not refined
S = 1.02	w = 1/[σ²(F_o²) + (0.1184P)² + 12.1765P] where P = (F_o² + 2F_c²)/3
3612 reflections	(Δ/σ)_max < 0.001
287 parameters	Δρ_max = 0.88 e Å⁻³
0 restraints	Δρ_min = −1.51 e Å⁻³

Crystal data top

[Ni₂Cd(C₁₇H₁₆N₂O₂)₂(C₂H₃O₂)₂(C₃H₇NO)₂]	V = 2334.4 (11) Å³
M_r = 1062.77	Z = 2
Monoclinic, P2₁/n	Mo Kα radiation
a = 10.285 (3) Å	µ = 1.31 mm⁻¹
b = 18.040 (5) Å	T = 295 K
c = 12.590 (3) Å	0.4 × 0.1 × 0.1 mm
β = 92.12 (2)°

Data collection top

Enraf–Nonius TurboCAD-4 diffractometer	1997 reflections with I > 2σ(I)
Absorption correction: ψ scan (North et al., 1968)	R_int = 0.076
T_min = 0.854, T_max = 0.877	3 standard reflections every 120 min
3960 measured reflections	intensity decay: 1%
3612 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.072	0 restraints
wR(F²) = 0.239	H-atom parameters not refined
S = 1.02	w = 1/[σ²(F_o²) + (0.1184P)² + 12.1765P] where P = (F_o² + 2F_c²)/3
3612 reflections	Δρ_max = 0.88 e Å⁻³
287 parameters	Δρ_min = −1.51 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

	x	y	z	U_iso*/U_eq
Cd	0	0	0	0.0489 (4)
Ni	0.03480 (12)	0.14386 (8)	−0.13762 (11)	0.0301 (4)
O5	−0.1184 (7)	0.1304 (4)	−0.2605 (6)	0.0409 (19)
O2	−0.0909 (6)	0.1061 (4)	−0.0260 (6)	0.0368 (18)
O1	0.0874 (7)	0.0355 (4)	−0.1446 (6)	0.0383 (18)
N2	−0.0396 (9)	0.2521 (5)	−0.1294 (7)	0.038 (2)
H2N	−0.0967	0.2576	−0.1858	0.045*
N1	0.1589 (9)	0.1727 (6)	−0.2591 (8)	0.044 (3)
H1N	0.1088	0.1762	−0.32	0.053*
C12	−0.2316 (10)	0.2091 (7)	−0.0309 (9)	0.041 (3)
C11	−0.1159 (10)	0.2610 (6)	−0.0316 (10)	0.041 (3)
H11A	−0.1463	0.3118	−0.0272	0.05*
H11B	−0.0598	0.2514	0.0304	0.05*
C1	0.1117 (10)	0.0039 (7)	−0.2371 (10)	0.041 (3)
C17	−0.2108 (10)	0.1325 (6)	−0.0246 (8)	0.035 (3)
N3	−0.3098 (9)	0.0735 (5)	−0.2942 (8)	0.044 (3)
C16	−0.3197 (10)	0.0877 (7)	−0.0137 (10)	0.044 (3)
H16	−0.3081	0.037	−0.0039	0.053*
C8	0.2249 (11)	0.2441 (8)	−0.2442 (11)	0.055 (4)
H8A	0.2818	0.2522	−0.3028	0.065*
H8B	0.2786	0.2422	−0.1793	0.065*
C6	0.1915 (11)	0.0396 (8)	−0.3095 (10)	0.053 (3)
C20	−0.1877 (10)	0.0758 (7)	−0.2586 (9)	0.043 (3)
H20	−0.1519	0.0326	−0.2298	0.051*
C10	0.0577 (11)	0.3126 (6)	−0.1368 (10)	0.047 (3)
H10A	0.1193	0.3093	−0.0768	0.056*
H10B	0.0136	0.36	−0.1326	0.056*
C5	0.2079 (15)	0.0093 (10)	−0.4079 (12)	0.077 (5)
H5	0.2562	0.0355	−0.4563	0.092*
C2	0.0636 (12)	−0.0651 (8)	−0.2658 (11)	0.059 (4)
H2	0.0165	−0.092	−0.2172	0.071*
C9	0.1305 (11)	0.3096 (7)	−0.2378 (11)	0.051 (4)
H9A	0.1791	0.3553	−0.2448	0.061*
H9B	0.0681	0.3068	−0.2974	0.061*
C15	−0.4443 (11)	0.1161 (8)	−0.0171 (10)	0.054 (3)
H15	−0.5152	0.0844	−0.0121	0.064*
C21	−0.3905 (14)	0.0079 (8)	−0.2850 (14)	0.085 (6)
H21A	−0.4761	0.018	−0.3146	0.128*
H21B	−0.3963	−0.0052	−0.2114	0.128*
H21C	−0.3526	−0.0324	−0.3228	0.128*
C22	−0.3729 (13)	0.1390 (8)	−0.3350 (13)	0.072 (5)
H22A	−0.4613	0.1276	−0.3561	0.108*
H22B	−0.3278	0.1568	−0.3953	0.108*
H22C	−0.372	0.1765	−0.2808	0.108*
C13	−0.3563 (11)	0.2387 (8)	−0.0343 (9)	0.049 (3)
H13	−0.369	0.2896	−0.0408	0.058*
O4	0.1691 (7)	0.1684 (4)	−0.0189 (6)	0.0365 (18)
O3	0.1560 (7)	0.0659 (4)	0.0804 (6)	0.0378 (18)
C18	0.1911 (9)	0.1297 (7)	0.0620 (9)	0.035 (3)
C14	−0.4637 (12)	0.1902 (9)	−0.0278 (10)	0.061 (4)
H14	−0.5479	0.2091	−0.0308	0.074*
C3	0.0837 (15)	−0.0952 (10)	−0.3644 (15)	0.083 (6)
H3	0.0483	−0.1412	−0.3821	0.1*
C4	0.157 (2)	−0.0572 (12)	−0.4381 (14)	0.093 (6)
H4	0.1702	−0.0767	−0.5052	0.112*
C7	0.2531 (12)	0.1124 (8)	−0.2753 (11)	0.060 (4)
H7A	0.3033	0.1046	−0.2095	0.071*
H7B	0.3129	0.1279	−0.3288	0.071*
C19	0.2689 (12)	0.1683 (7)	0.1523 (10)	0.053 (3)
H19A	0.2146	0.1748	0.212	0.079*
H19B	0.298	0.2158	0.1283	0.079*
H19C	0.3428	0.1384	0.173	0.079*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cd	0.0419 (7)	0.0521 (8)	0.0523 (10)	−0.0009 (6)	−0.0042 (6)	0.0037 (7)
Ni	0.0200 (6)	0.0433 (8)	0.0269 (8)	−0.0003 (6)	−0.0022 (5)	0.0011 (6)
O5	0.034 (4)	0.050 (5)	0.037 (5)	−0.005 (4)	−0.010 (3)	−0.002 (4)
O2	0.022 (4)	0.047 (5)	0.042 (5)	0.001 (3)	0.002 (3)	0.001 (4)
O1	0.033 (4)	0.044 (5)	0.038 (5)	0.000 (3)	0.002 (3)	−0.005 (4)
N2	0.039 (5)	0.046 (6)	0.029 (6)	−0.002 (4)	−0.003 (4)	0.002 (4)
N1	0.036 (5)	0.060 (7)	0.037 (7)	−0.004 (5)	0.003 (4)	0.010 (5)
C12	0.030 (6)	0.057 (8)	0.036 (8)	0.010 (6)	0.003 (5)	−0.002 (6)
C11	0.036 (6)	0.043 (7)	0.044 (8)	0.013 (5)	−0.007 (5)	0.001 (6)
C1	0.025 (5)	0.052 (7)	0.044 (8)	0.014 (6)	0.001 (5)	−0.009 (6)
C17	0.035 (6)	0.050 (7)	0.020 (6)	0.001 (5)	−0.003 (4)	−0.006 (5)
N3	0.037 (5)	0.053 (6)	0.043 (7)	−0.011 (5)	−0.015 (4)	0.011 (5)
C16	0.028 (6)	0.057 (8)	0.048 (8)	−0.013 (5)	0.005 (5)	−0.008 (6)
C8	0.030 (7)	0.085 (10)	0.048 (9)	−0.004 (7)	0.002 (6)	0.012 (7)
C6	0.037 (7)	0.077 (10)	0.043 (9)	0.016 (7)	−0.003 (6)	−0.011 (7)
C20	0.033 (6)	0.052 (8)	0.040 (8)	0.014 (6)	−0.023 (5)	−0.007 (6)
C10	0.052 (8)	0.041 (7)	0.046 (9)	−0.007 (6)	−0.003 (6)	0.004 (6)
C5	0.080 (11)	0.111 (15)	0.042 (10)	0.042 (10)	0.025 (8)	−0.008 (9)
C2	0.046 (7)	0.070 (10)	0.061 (10)	0.016 (7)	0.014 (6)	−0.013 (8)
C9	0.041 (7)	0.049 (8)	0.061 (9)	−0.023 (6)	−0.017 (6)	0.029 (7)
C15	0.030 (6)	0.082 (10)	0.050 (9)	−0.011 (7)	0.003 (6)	−0.001 (7)
C21	0.074 (10)	0.069 (10)	0.110 (15)	−0.031 (8)	−0.045 (10)	0.018 (9)
C22	0.046 (8)	0.065 (10)	0.103 (13)	−0.009 (7)	−0.028 (8)	0.036 (9)
C13	0.039 (7)	0.070 (9)	0.037 (8)	0.019 (6)	−0.001 (5)	0.005 (6)
O4	0.033 (4)	0.049 (5)	0.028 (5)	−0.005 (3)	−0.010 (3)	0.007 (4)
O3	0.039 (4)	0.041 (5)	0.033 (5)	−0.001 (4)	−0.007 (3)	0.006 (3)
C18	0.020 (5)	0.054 (8)	0.031 (8)	0.009 (5)	−0.006 (4)	−0.010 (6)
C14	0.028 (7)	0.113 (14)	0.043 (9)	0.017 (8)	−0.003 (5)	0.000 (8)
C3	0.055 (10)	0.109 (14)	0.084 (14)	0.037 (9)	−0.017 (9)	−0.055 (11)
C4	0.111 (15)	0.121 (17)	0.048 (12)	0.057 (13)	−0.005 (10)	−0.040 (11)
C7	0.030 (7)	0.092 (11)	0.058 (10)	0.012 (7)	0.016 (6)	0.013 (8)
C19	0.053 (8)	0.058 (8)	0.044 (9)	−0.004 (6)	−0.018 (6)	0.004 (6)

Geometric parameters (Å, º) top

Cd—Ni	3.1482 (15)	C8—H8A	0.97
Cd—O1	2.157 (7)	C8—H8B	0.97
Cd—O2	2.151 (7)	C6—C5	1.370 (19)
Cd—O3	2.212 (7)	C6—C7	1.514 (19)
Ni—N1	2.094 (9)	C20—H20	0.93
Ni—N2	2.101 (9)	C10—C9	1.500 (17)
Ni—O1	2.031 (8)	C10—H10A	0.97
Ni—O2	2.060 (7)	C10—H10B	0.97
Ni—O4	2.045 (7)	C5—C4	1.36 (2)
Ni—O5	2.180 (7)	C5—H5	0.93
Cd—O2ⁱ	2.151 (7)	C2—C3	1.38 (2)
Cd—O1ⁱ	2.157 (7)	C2—H2	0.93
Cd—O3ⁱ	2.212 (7)	C9—H9A	0.97
Cd—Niⁱ	3.1482 (15)	C9—H9B	0.97
O5—C20	1.217 (13)	C15—C14	1.358 (19)
O2—C17	1.323 (12)	C15—H15	0.93
O1—C1	1.328 (13)	C21—H21A	0.96
N2—C10	1.486 (14)	C21—H21B	0.96
N2—C11	1.493 (14)	C21—H21C	0.96
N2—H2N	0.91	C22—H22A	0.96
N1—C8	1.465 (15)	C22—H22B	0.96
N1—C7	1.474 (15)	C22—H22C	0.96
N1—H1N	0.91	C13—C14	1.415 (18)
C12—C13	1.389 (15)	C13—H13	0.93
C12—C17	1.400 (16)	O4—C18	1.248 (13)
C12—C11	1.514 (16)	O3—C18	1.231 (13)
C11—H11A	0.97	C18—C19	1.532 (15)
C11—H11B	0.97	C14—H14	0.93
C1—C2	1.384 (17)	C3—C4	1.40 (3)
C1—C6	1.405 (17)	C3—H3	0.93
C17—C16	1.392 (14)	C4—H4	0.93
N3—C20	1.319 (13)	C7—H7A	0.97
N3—C22	1.435 (15)	C7—H7B	0.97
N3—C21	1.452 (15)	C19—H19A	0.96
C16—C15	1.379 (16)	C19—H19B	0.96
C16—H16	0.93	C19—H19C	0.96
C8—C9	1.534 (17)

O1—Cd—O2	78.4 (3)	C16—C17—C12	117.2 (10)
O1—Cd—O2ⁱ	101.6 (3)	C20—N3—C22	120.5 (10)
O1—Cd—O3	84.8 (3)	C20—N3—C21	122.6 (11)
O2—Cd—O3	83.9 (3)	C22—N3—C21	116.6 (10)
O1—Ni—O2	83.5 (3)	C15—C16—C17	122.1 (12)
O1—Ni—O4	93.8 (3)	C15—C16—H16	118.9
O1—Ni—N1	92.1 (3)	C17—C16—H16	118.9
O1—Ni—O5	92.8 (3)	N1—C8—C9	113.2 (9)
O2—Ni—N2	92.0 (3)	N1—C8—H8A	108.9
O2—Ni—O5	89.6 (3)	C9—C8—H8A	108.9
O4—Ni—O2	89.8 (3)	N1—C8—H8B	108.9
O4—Ni—N1	93.8 (3)	C9—C8—H8B	108.9
O4—Ni—N2	90.0 (3)	H8A—C8—H8B	107.8
N1—Ni—N2	92.2 (4)	C5—C6—C1	119.9 (14)
N1—Ni—O5	87.3 (3)	C5—C6—C7	122.7 (14)
N2—Ni—O5	83.3 (3)	C1—C6—C7	117.4 (11)
Ni—O1—Cd	97.4 (3)	O5—C20—N3	124.8 (11)
Ni—O2—Cd	96.8 (3)	O5—C20—H20	117.6
O2—Cd—O2ⁱ	180.0 (4)	N3—C20—H20	117.6
O1ⁱ—Cd—O2	101.6 (3)	N2—C10—C9	112.6 (9)
O2ⁱ—Cd—O1ⁱ	78.4 (3)	N2—C10—H10A	109.1
O1ⁱ—Cd—O1	180.0 (5)	C9—C10—H10A	109.1
O2—Cd—O3ⁱ	96.1 (3)	N2—C10—H10B	109.1
O2ⁱ—Cd—O3ⁱ	83.9 (3)	C9—C10—H10B	109.1
O1ⁱ—Cd—O3ⁱ	84.8 (3)	H10A—C10—H10B	107.8
O1—Cd—O3ⁱ	95.2 (3)	C4—C5—C6	123.2 (17)
O2ⁱ—Cd—O3	96.1 (3)	C4—C5—H5	118.4
O1ⁱ—Cd—O3	95.2 (3)	C6—C5—H5	118.4
O3ⁱ—Cd—O3	180.0 (6)	C3—C2—C1	121.7 (15)
O2—Cd—Ni	40.53 (19)	C3—C2—H2	119.2
O2ⁱ—Cd—Ni	139.47 (19)	C1—C2—H2	119.2
O1ⁱ—Cd—Ni	140.2 (2)	C10—C9—C8	114.1 (10)
O1—Cd—Ni	39.8 (2)	C10—C9—H9A	108.7
O3ⁱ—Cd—Ni	106.67 (19)	C8—C9—H9A	108.7
O3—Cd—Ni	73.33 (19)	C10—C9—H9B	108.7
O2—Cd—Niⁱ	139.47 (19)	C8—C9—H9B	108.7
O2ⁱ—Cd—Niⁱ	40.53 (19)	H9A—C9—H9B	107.6
O1ⁱ—Cd—Niⁱ	39.8 (2)	C14—C15—C16	120.1 (12)
O1—Cd—Niⁱ	140.2 (2)	C14—C15—H15	120
O3ⁱ—Cd—Niⁱ	73.33 (19)	C16—C15—H15	120
O3—Cd—Niⁱ	106.67 (19)	N3—C21—H21A	109.5
Ni—Cd—Niⁱ	180	N3—C21—H21B	109.5
O2—Ni—N1	174.5 (4)	H21A—C21—H21B	109.5
O1—Ni—N2	174.1 (3)	N3—C21—H21C	109.5
O4—Ni—O5	173.3 (3)	H21A—C21—H21C	109.5
O1—Ni—Cd	42.8 (2)	H21B—C21—H21C	109.5
O4—Ni—Cd	82.2 (2)	N3—C22—H22A	109.5
O2—Ni—Cd	42.7 (2)	N3—C22—H22B	109.5
N1—Ni—Cd	133.7 (3)	H22A—C22—H22B	109.5
N2—Ni—Cd	133.6 (3)	N3—C22—H22C	109.5
O5—Ni—Cd	101.8 (2)	H22A—C22—H22C	109.5
C20—O5—Ni	118.9 (7)	H22B—C22—H22C	109.5
C17—O2—Ni	119.9 (7)	C12—C13—C14	118.8 (13)
C17—O2—Cd	136.0 (7)	C12—C13—H13	120.6
C1—O1—Ni	120.7 (7)	C14—C13—H13	120.6
C1—O1—Cd	135.3 (7)	C18—O4—Ni	125.0 (7)
C10—N2—C11	110.4 (9)	C18—O3—Cd	129.0 (7)
C10—N2—Ni	115.6 (7)	O3—C18—O4	129.0 (10)
C11—N2—Ni	110.1 (7)	O3—C18—C19	115.7 (10)
C10—N2—H2N	106.7	O4—C18—C19	115.2 (10)
C11—N2—H2N	106.7	C15—C14—C13	120.2 (11)
Ni—N2—H2N	106.7	C15—C14—H14	119.9
C8—N1—C7	111.3 (9)	C13—C14—H14	119.9
C8—N1—Ni	114.6 (7)	C2—C3—C4	120.6 (17)
C7—N1—Ni	109.8 (7)	C2—C3—H3	119.7
C8—N1—H1N	106.9	C4—C3—H3	119.7
C7—N1—H1N	106.9	C5—C4—C3	117.3 (15)
Ni—N1—H1N	106.9	C5—C4—H4	121.3
C13—C12—C17	121.3 (11)	C3—C4—H4	121.3
C13—C12—C11	119.2 (11)	N1—C7—C6	114.1 (10)
C17—C12—C11	119.5 (9)	N1—C7—H7A	108.7
N2—C11—C12	112.1 (9)	C6—C7—H7A	108.7
N2—C11—H11A	109.2	N1—C7—H7B	108.7
C12—C11—H11A	109.2	C6—C7—H7B	108.7
N2—C11—H11B	109.2	H7A—C7—H7B	107.6
C12—C11—H11B	109.2	C18—C19—H19A	109.5
H11A—C11—H11B	107.9	C18—C19—H19B	109.5
O1—C1—C2	122.5 (11)	H19A—C19—H19B	109.5
O1—C1—C6	120.4 (11)	C18—C19—H19C	109.5
C2—C1—C6	117.1 (12)	H19A—C19—H19C	109.5
O2—C17—C16	123.1 (10)	H19B—C19—H19C	109.5
O2—C17—C12	119.7 (10)

O2—Cd—Ni—O1	−157.4 (4)	N1—Ni—N2—C10	−41.5 (8)
O2ⁱ—Cd—Ni—O1	22.6 (4)	O5—Ni—N2—C10	−128.5 (8)
O1ⁱ—Cd—Ni—O1	180	Cd—Ni—N2—C10	131.5 (7)
O3ⁱ—Cd—Ni—O1	−77.8 (4)	O4—Ni—N2—C11	−73.7 (7)
O3—Cd—Ni—O1	102.2 (4)	O2—Ni—N2—C11	16.2 (7)
O2—Cd—Ni—O4	98.3 (4)	N1—Ni—N2—C11	−167.5 (7)
O2ⁱ—Cd—Ni—O4	−81.7 (4)	O5—Ni—N2—C11	105.5 (7)
O1ⁱ—Cd—Ni—O4	75.7 (4)	Cd—Ni—N2—C11	5.5 (8)
O1—Cd—Ni—O4	−104.3 (4)	O1—Ni—N1—C8	−141.8 (7)
O3ⁱ—Cd—Ni—O4	177.9 (3)	O4—Ni—N1—C8	−47.9 (8)
O3—Cd—Ni—O4	−2.1 (3)	N2—Ni—N1—C8	42.3 (8)
O2ⁱ—Cd—Ni—O2	180	O5—Ni—N1—C8	125.5 (8)
O1ⁱ—Cd—Ni—O2	−22.6 (4)	Cd—Ni—N1—C8	−130.7 (7)
O1—Cd—Ni—O2	157.4 (4)	O1—Ni—N1—C7	−15.7 (8)
O3ⁱ—Cd—Ni—O2	79.6 (4)	O4—Ni—N1—C7	78.2 (8)
O3—Cd—Ni—O2	−100.4 (4)	N2—Ni—N1—C7	168.4 (8)
O2—Cd—Ni—N1	−173.9 (5)	O5—Ni—N1—C7	−108.4 (8)
O2ⁱ—Cd—Ni—N1	6.1 (5)	Cd—Ni—N1—C7	−4.6 (10)
O1ⁱ—Cd—Ni—N1	163.5 (5)	C10—N2—C11—C12	169.7 (9)
O1—Cd—Ni—N1	−16.5 (5)	Ni—N2—C11—C12	−61.4 (10)
O3ⁱ—Cd—Ni—N1	−94.3 (4)	C13—C12—C11—N2	−115.3 (11)
O3—Cd—Ni—N1	85.7 (4)	C17—C12—C11—N2	66.0 (13)
O2—Cd—Ni—N2	15.8 (4)	Ni—O1—C1—C2	−134.8 (10)
O2ⁱ—Cd—Ni—N2	−164.2 (4)	Cd—O1—C1—C2	9.5 (16)
O1ⁱ—Cd—Ni—N2	−6.8 (5)	Ni—O1—C1—C6	46.8 (12)
O1—Cd—Ni—N2	173.2 (5)	Cd—O1—C1—C6	−168.9 (8)
O3ⁱ—Cd—Ni—N2	95.4 (4)	Ni—O2—C17—C16	135.0 (9)
O3—Cd—Ni—N2	−84.6 (4)	Cd—O2—C17—C16	−7.2 (16)
O2—Cd—Ni—O5	−76.2 (4)	Ni—O2—C17—C12	−47.0 (12)
O2ⁱ—Cd—Ni—O5	103.8 (4)	Cd—O2—C17—C12	170.7 (8)
O1ⁱ—Cd—Ni—O5	−98.8 (4)	C13—C12—C17—O2	177.2 (10)
O1—Cd—Ni—O5	81.2 (4)	C11—C12—C17—O2	−4.2 (16)
O3ⁱ—Cd—Ni—O5	3.4 (3)	C13—C12—C17—C16	−4.8 (16)
O3—Cd—Ni—O5	−176.6 (3)	C11—C12—C17—C16	173.9 (10)
O1—Ni—O5—C20	42.4 (9)	O2—C17—C16—C15	−177.1 (11)
O2—Ni—O5—C20	−41.0 (8)	C12—C17—C16—C15	4.9 (17)
N1—Ni—O5—C20	134.4 (9)	C7—N1—C8—C9	174.4 (10)
N2—Ni—O5—C20	−133.1 (9)	Ni—N1—C8—C9	−60.2 (11)
Cd—Ni—O5—C20	0.2 (9)	O1—C1—C6—C5	−175.0 (11)
O1—Ni—O2—C17	−139.4 (8)	C2—C1—C6—C5	6.5 (17)
O4—Ni—O2—C17	126.8 (7)	O1—C1—C6—C7	3.1 (16)
N2—Ni—O2—C17	36.8 (8)	C2—C1—C6—C7	−175.3 (11)
O5—Ni—O2—C17	−46.5 (7)	Ni—O5—C20—N3	150.1 (10)
Cd—Ni—O2—C17	−154.6 (9)	C22—N3—C20—O5	−3 (2)
O1—Ni—O2—Cd	15.2 (3)	C21—N3—C20—O5	−176.7 (13)
O4—Ni—O2—Cd	−78.6 (3)	C11—N2—C10—C9	−175.7 (9)
N2—Ni—O2—Cd	−168.6 (3)	Ni—N2—C10—C9	58.4 (11)
O5—Ni—O2—Cd	108.1 (3)	C1—C6—C5—C4	−4 (2)
O1ⁱ—Cd—O2—C17	−46.8 (10)	C7—C6—C5—C4	177.6 (14)
O1—Cd—O2—C17	133.2 (10)	O1—C1—C2—C3	176.3 (11)
O3ⁱ—Cd—O2—C17	39.1 (10)	C6—C1—C2—C3	−5.3 (18)
O3—Cd—O2—C17	−140.9 (10)	N2—C10—C9—C8	−69.7 (13)
Ni—Cd—O2—C17	147.7 (11)	N1—C8—C9—C10	71.7 (13)
Niⁱ—Cd—O2—C17	−32.3 (11)	C17—C16—C15—C14	−2.2 (19)
O1ⁱ—Cd—O2—Ni	165.5 (3)	C17—C12—C13—C14	2.1 (17)
O1—Cd—O2—Ni	−14.5 (3)	C11—C12—C13—C14	−176.6 (11)
O3ⁱ—Cd—O2—Ni	−108.7 (3)	O1—Ni—O4—C18	−44.8 (8)
O3—Cd—O2—Ni	71.3 (3)	O2—Ni—O4—C18	38.6 (8)
Niⁱ—Cd—O2—Ni	180	N1—Ni—O4—C18	−137.2 (9)
O4—Ni—O1—C1	−130.3 (8)	N2—Ni—O4—C18	130.6 (9)
O2—Ni—O1—C1	140.3 (8)	Cd—Ni—O4—C18	−3.5 (8)
N1—Ni—O1—C1	−36.3 (8)	O2—Cd—O3—C18	−30.5 (9)
O5—Ni—O1—C1	51.1 (8)	O2ⁱ—Cd—O3—C18	149.5 (9)
Cd—Ni—O1—C1	155.5 (9)	O1ⁱ—Cd—O3—C18	−131.6 (9)
O4—Ni—O1—Cd	74.2 (3)	O1—Cd—O3—C18	48.4 (9)
O2—Ni—O1—Cd	−15.2 (3)	Ni—Cd—O3—C18	9.5 (8)
N1—Ni—O1—Cd	168.1 (3)	Niⁱ—Cd—O3—C18	−170.5 (8)
O5—Ni—O1—Cd	−104.4 (3)	Cd—O3—C18—O4	−17.1 (17)
O2—Cd—O1—C1	−134.8 (9)	Cd—O3—C18—C19	160.6 (7)
O2ⁱ—Cd—O1—C1	45.2 (9)	Ni—O4—C18—O3	12.9 (16)
O3ⁱ—Cd—O1—C1	−39.7 (9)	Ni—O4—C18—C19	−164.9 (7)
O3—Cd—O1—C1	140.3 (9)	C16—C15—C14—C13	−1 (2)
Ni—Cd—O1—C1	−149.6 (10)	C12—C13—C14—C15	0.8 (18)
Niⁱ—Cd—O1—C1	30.4 (10)	C1—C2—C3—C4	2 (2)
O2—Cd—O1—Ni	14.8 (3)	C6—C5—C4—C3	1 (2)
O2ⁱ—Cd—O1—Ni	−165.2 (3)	C2—C3—C4—C5	1 (2)
O3ⁱ—Cd—O1—Ni	109.9 (3)	C8—N1—C7—C6	−170.3 (11)
O3—Cd—O1—Ni	−70.1 (3)	Ni—N1—C7—C6	61.8 (12)
Niⁱ—Cd—O1—Ni	180	C5—C6—C7—N1	113.1 (14)
O4—Ni—N2—C10	52.3 (8)	C1—C6—C7—N1	−64.9 (15)
O2—Ni—N2—C10	142.1 (8)

Symmetry code: (i) −x, −y, −z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O3ⁱ	0.93	2.56	3.308 (16)	138
C20—H20···O3ⁱ	0.93	2.59	3.409 (14)	147

Symmetry code: (i) −x, −y, −z.

Experimental details

Crystal data
Chemical formula	[Ni₂Cd(C₁₇H₁₆N₂O₂)₂(C₂H₃O₂)₂(C₃H₇NO)₂]
M_r	1062.77
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	295
a, b, c (Å)	10.285 (3), 18.040 (5), 12.590 (3)
β (°)	92.12 (2)
V (Å³)	2334.4 (11)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.31
Crystal size (mm)	0.4 × 0.1 × 0.1

Data collection
Diffractometer	Enraf–Nonius TurboCAD-4 diffractometer
Absorption correction	ψ scan (North et al., 1968)
T_min, T_max	0.854, 0.877
No. of measured, independent and observed [I > 2σ(I)] reflections	3960, 3612, 1997
R_int	0.076
(sin θ/λ)_max (Å⁻¹)	0.596

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.072, 0.239, 1.02
No. of reflections	3612
No. of parameters	287
H-atom treatment	H-atom parameters not refined
	w = 1/[σ²(F_o²) + (0.1184P)² + 12.1765P] where P = (F_o² + 2F_c²)/3
Δρ_max, Δρ_min (e Å⁻³)	0.88, −1.51

Computer programs: CAD-4 EXPRESS (Enraf–Nonius, 1994), XCAD4 (Harms & Wocadlo, 1995), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).

Selected bond lengths (Å) top

Cd—O1	2.157 (7)	Ni—O1	2.031 (8)
Cd—O2	2.151 (7)	Ni—O2	2.060 (7)
Cd—O3	2.212 (7)	Ni—O4	2.045 (7)
Ni—N1	2.094 (9)	Ni—O5	2.180 (7)
Ni—N2	2.101 (9)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O3ⁱ	0.93	2.56	3.308 (16)	138
C20—H20···O3ⁱ	0.93	2.59	3.409 (14)	147

Symmetry code: (i) −x, −y, −z.

Acknowledgements

We are grateful to Hacettepe University Scientific Research Unit (grant No. 04 A602004) for financial support.

References

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Volume 64| Part 2| February 2008| Pages m291-m292

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