metal-organic compounds
cis-Dichlorido[4,4,5,5-tetramethyl-2-(2-pyridyl)-2-imidazoline-1-oxyl]palladium(II) tetrahydrofuran hemisolvate
aLaboratoire de Chimie Moléculaire, du Contrôle de l'Environnement et de Mesures Physico-Chimiques, Département de Chimie, Université Frères Mentouri, Constantine, Algeria, and bSciences Chimiques de Rennes, UMR 6226, CNRS–Université de Rennes 1, 263 Avenue du Général Leclerc, CS 74205, 35042 Rennes Cedex, France
*Correspondence e-mail: s_badeche@yahoo.fr
The 2(C12H16N3O)]·0.5C4H8O, consists of one palladium complex in a general position and one half tetrahydrofuran (THF) solvent molecule, with the O atom lying on a twofold rotation axis. The PdII atom is bound to one chelating imino nitroxide radical through two N atoms, one from the pyridyl ring and the other from the imidazoline ring. The coordination of the metal centre is completed by two Cl atoms in a cis configuration, leading to a quasi-square-planar coordination of the metal centre. The four atoms that define the PdII coordination environment and the eight atoms that belong to the pyridylimine fragment are coplanar, with no deviation larger than 0.087 (5) Å. In the intermolecular interactions shorter than the corresponding van der Waals radii sum are observed only between PdII complexes, and no short contact is observed around the THF molecule. Weak C—H⋯O and C—H⋯Cl interactions yield a two-dimensional network of complexes in the (101) plane.
of the title complex, [PdClRelated literature
For related literature, see: Caneschi et al. (1991); Davis et al. (1972); Evans et al. (1968); Fettouhi et al. (2003); Li et al. (2004); Ma et al. (2006, 2007); Oshio et al. (1996); Ueda et al. (2003, 2005); Ullman & Holm (1970); Xu et al. (2007).
Experimental
Crystal data
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Data collection
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Refinement
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Data collection: COLLECT (Nonius, 2000); cell HKL SCALEPACK (Otwinowski & Minor, 1997); data reduction: HKL DENZO (Otwinowski & Minor, 1997) and SCALEPACK; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and Mercury (Macrae et al., 2006); software used to prepare material for publication: WinGX (Farrugia, 1999).
Supporting information
10.1107/S1600536808004406/dn2318sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536808004406/dn2318Isup2.hkl
Dichlorobis benzonitrile palladium(II) PdCl2(PhCN)2 and 2-(ortho- pyridyl)-4,4,5,5-tetramethyl imidazoline-1-oxyl-3-oxyde (NIT2Py) were synthesized according to literature method (Evans et al., 1968; Ullman & Holm, 1970; Davis et al., 1972). The complex Pd(IM2py)Cl2 was synthesized as follows: The reaction was performed under a dry nitrogen atmosphere using standard schlenk technique. All solvents used were distilled under nitrogen. To a solution of PdCl2(PhCN)2 (0.1 g;0.26 mmol) in 30 ml of toluene was added with stirring a solution of the radical NIT2Py (0.12 g;0.52 mmol) in 20 ml of toluene. After 2 h of stirring at room temperature, the mixture was filtered and the solvent removed under reduced pressure. Parallelepipedic brown crystals of complex (I) suitable for x-ray crystallographic analysis were obtained by slow diffusion of hexane in THF solution of complex (I).
All H atoms were placed in calculated positions and treated as riding model with C—H ranging from 0.93 Å [Uiso(H) = 1.2Ueq(C)] for pyridyl ring to 0.96—0.97 Å with Uiso(H) = 1.5Ueq(C)—1.2Ueq(C)) for methyl and methylene respectively.
Data collection: Collect (Nonius, 2000); cell
HKL SCALEPACK (Otwinowski & Minor, 1997); data reduction: HKL DENZO and SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and Mercury (Macrae et al., 2006); software used to prepare material for publication: WinGX (Farrugia, 1999).[PdCl2(C12H16N3O)]·0.5C4H8O | F(000) = 1736 |
Mr = 431.65 | Dx = 1.707 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -C 2yc | Cell parameters from 2981 reflections |
a = 19.1398 (10) Å | θ = 2.6–25.4° |
b = 15.2061 (12) Å | µ = 1.43 mm−1 |
c = 13.8291 (10) Å | T = 293 K |
β = 123.415 (3)° | Thick plate, brown |
V = 3359.6 (4) Å3 | 0.7 × 0.3 × 0.3 mm |
Z = 8 |
Nonius KappaCCD diffractometer | 2049 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.059 |
Graphite monochromator | θmax = 25.4°, θmin = 3.0° |
ϕ and ω scans | h = −22→22 |
5707 measured reflections | k = −17→18 |
3065 independent reflections | l = −16→16 |
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)] = 0.057 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.152 | H-atom parameters constrained |
S = 1.03 | w = 1/[σ2(Fo2) + (0.0709P)2 + 4.5052P] where P = (Fo2 + 2Fc2)/3 |
3065 reflections | (Δ/σ)max = 0.001 |
199 parameters | Δρmax = 0.61 e Å−3 |
0 restraints | Δρmin = −0.95 e Å−3 |
[PdCl2(C12H16N3O)]·0.5C4H8O | V = 3359.6 (4) Å3 |
Mr = 431.65 | Z = 8 |
Monoclinic, C2/c | Mo Kα radiation |
a = 19.1398 (10) Å | µ = 1.43 mm−1 |
b = 15.2061 (12) Å | T = 293 K |
c = 13.8291 (10) Å | 0.7 × 0.3 × 0.3 mm |
β = 123.415 (3)° |
Nonius KappaCCD diffractometer | 2049 reflections with I > 2σ(I) |
5707 measured reflections | Rint = 0.059 |
3065 independent reflections |
R[F2 > 2σ(F2)] = 0.057 | 0 restraints |
wR(F2) = 0.152 | H-atom parameters constrained |
S = 1.03 | Δρmax = 0.61 e Å−3 |
3065 reflections | Δρmin = −0.95 e Å−3 |
199 parameters |
Experimental. Multiscan absorption correction methods did not yield a better refinement agreement, then no correction was applied. |
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 | ||
C1 | 0.4332 (5) | 0.2973 (4) | 0.6038 (6) | 0.0604 (18) | |
H1 | 0.4196 | 0.3511 | 0.6214 | 0.073* | |
C2 | 0.4905 (5) | 0.2955 (5) | 0.5741 (8) | 0.072 (2) | |
H2 | 0.5154 | 0.3475 | 0.5723 | 0.087* | |
C3 | 0.5113 (5) | 0.2173 (5) | 0.5470 (6) | 0.0603 (18) | |
H3 | 0.5497 | 0.2151 | 0.5258 | 0.072* | |
C4 | 0.4733 (5) | 0.1419 (4) | 0.5520 (6) | 0.0558 (18) | |
H4 | 0.4851 | 0.0877 | 0.5330 | 0.067* | |
C5 | 0.4172 (4) | 0.1475 (4) | 0.5858 (5) | 0.0443 (14) | |
C6 | 0.3741 (4) | 0.0747 (4) | 0.5988 (5) | 0.0445 (14) | |
C7 | 0.3264 (5) | −0.0669 (4) | 0.6000 (6) | 0.0560 (17) | |
C8 | 0.2934 (4) | 0.0028 (4) | 0.6501 (6) | 0.0498 (16) | |
C9 | 0.2604 (6) | −0.0980 (6) | 0.4783 (7) | 0.081 (2) | |
H9A | 0.2328 | −0.0479 | 0.4294 | 0.122* | |
H9B | 0.2201 | −0.1339 | 0.4806 | 0.122* | |
H9C | 0.2867 | −0.1317 | 0.4480 | 0.122* | |
C10 | 0.3725 (5) | −0.1451 (5) | 0.6789 (8) | 0.078 (2) | |
H10A | 0.3899 | −0.1843 | 0.6415 | 0.117* | |
H10B | 0.3359 | −0.1757 | 0.6946 | 0.117* | |
H10C | 0.4208 | −0.1246 | 0.7503 | 0.117* | |
C11 | 0.1983 (5) | 0.0032 (5) | 0.5897 (7) | 0.076 (2) | |
H11A | 0.1824 | 0.0501 | 0.6202 | 0.114* | |
H11B | 0.1805 | −0.0520 | 0.6030 | 0.114* | |
H11C | 0.1723 | 0.0116 | 0.5080 | 0.114* | |
C12 | 0.3364 (5) | −0.0032 (5) | 0.7811 (6) | 0.067 (2) | |
H12A | 0.3951 | −0.0143 | 0.8167 | 0.101* | |
H12B | 0.3121 | −0.0502 | 0.7994 | 0.101* | |
H12C | 0.3292 | 0.0513 | 0.8098 | 0.101* | |
N1 | 0.3961 (3) | 0.2250 (3) | 0.6084 (5) | 0.0470 (12) | |
N2 | 0.3857 (4) | −0.0129 (3) | 0.5888 (5) | 0.0512 (13) | |
N3 | 0.3211 (3) | 0.0884 (3) | 0.6270 (5) | 0.0509 (13) | |
O1 | 0.4363 (3) | −0.0447 (3) | 0.5657 (5) | 0.0687 (14) | |
Cl1 | 0.21890 (16) | 0.20499 (14) | 0.7093 (2) | 0.0865 (7) | |
Cl2 | 0.30744 (14) | 0.36626 (13) | 0.67356 (19) | 0.0761 (6) | |
Pd1 | 0.30983 (3) | 0.21827 (3) | 0.65241 (5) | 0.0534 (2) | |
O1S | 0.5000 | 0.4980 (7) | 0.7500 | 0.177 (7) | |
C2S | 0.5251 (8) | 0.5487 (7) | 0.6926 (10) | 0.108 (3) | |
H2S1 | 0.4949 | 0.5319 | 0.6116 | 0.130* | |
H2S2 | 0.5845 | 0.5408 | 0.7263 | 0.130* | |
C3S | 0.5078 (9) | 0.6386 (6) | 0.7032 (11) | 0.118 (4) | |
H3S1 | 0.4590 | 0.6595 | 0.6312 | 0.142* | |
H3S2 | 0.5552 | 0.6758 | 0.7235 | 0.142* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.069 (5) | 0.050 (4) | 0.066 (5) | 0.003 (3) | 0.040 (4) | −0.004 (3) |
C2 | 0.077 (6) | 0.059 (5) | 0.091 (6) | −0.023 (4) | 0.052 (5) | −0.002 (4) |
C3 | 0.060 (4) | 0.068 (5) | 0.065 (5) | −0.006 (4) | 0.041 (4) | 0.000 (4) |
C4 | 0.071 (5) | 0.053 (4) | 0.064 (5) | 0.003 (3) | 0.050 (4) | 0.003 (3) |
C5 | 0.050 (4) | 0.045 (3) | 0.039 (3) | −0.002 (3) | 0.026 (3) | −0.002 (3) |
C6 | 0.050 (4) | 0.046 (3) | 0.048 (4) | 0.004 (3) | 0.034 (3) | 0.003 (3) |
C7 | 0.068 (5) | 0.046 (3) | 0.073 (5) | −0.006 (3) | 0.050 (4) | 0.001 (3) |
C8 | 0.050 (4) | 0.053 (4) | 0.054 (4) | 0.000 (3) | 0.034 (4) | 0.008 (3) |
C9 | 0.095 (7) | 0.079 (5) | 0.083 (6) | −0.018 (5) | 0.057 (6) | −0.017 (5) |
C10 | 0.100 (7) | 0.060 (5) | 0.105 (7) | 0.009 (4) | 0.075 (6) | 0.022 (4) |
C11 | 0.061 (5) | 0.085 (6) | 0.091 (6) | −0.010 (4) | 0.048 (5) | 0.000 (5) |
C12 | 0.074 (5) | 0.078 (5) | 0.060 (5) | −0.003 (4) | 0.044 (4) | 0.005 (4) |
N1 | 0.051 (3) | 0.043 (3) | 0.049 (3) | −0.002 (2) | 0.029 (3) | 0.002 (2) |
N2 | 0.059 (3) | 0.043 (3) | 0.067 (4) | 0.006 (3) | 0.044 (3) | 0.006 (2) |
N3 | 0.056 (3) | 0.052 (3) | 0.057 (3) | 0.006 (3) | 0.039 (3) | 0.005 (2) |
O1 | 0.083 (4) | 0.052 (3) | 0.103 (4) | 0.014 (3) | 0.072 (4) | 0.004 (3) |
Cl1 | 0.0970 (17) | 0.0960 (15) | 0.1066 (18) | 0.0216 (13) | 0.0814 (16) | 0.0034 (12) |
Cl2 | 0.0873 (15) | 0.0578 (10) | 0.0865 (15) | 0.0200 (10) | 0.0499 (13) | −0.0037 (9) |
Pd1 | 0.0586 (4) | 0.0552 (3) | 0.0549 (4) | 0.0116 (3) | 0.0366 (3) | −0.0002 (2) |
O1S | 0.249 (17) | 0.068 (6) | 0.35 (2) | 0.000 | 0.246 (18) | 0.000 |
C2S | 0.116 (9) | 0.094 (7) | 0.134 (10) | −0.007 (6) | 0.081 (8) | −0.014 (7) |
C3S | 0.178 (12) | 0.073 (6) | 0.142 (10) | −0.025 (7) | 0.113 (10) | −0.009 (6) |
C1—N1 | 1.329 (8) | C10—H10A | 0.9600 |
C1—C2 | 1.367 (11) | C10—H10B | 0.9600 |
C1—H1 | 0.9300 | C10—H10C | 0.9600 |
C2—C3 | 1.370 (10) | C11—H11A | 0.9600 |
C2—H2 | 0.9300 | C11—H11B | 0.9600 |
C3—C4 | 1.381 (9) | C11—H11C | 0.9600 |
C3—H3 | 0.9300 | C12—H12A | 0.9600 |
C4—C5 | 1.388 (8) | C12—H12B | 0.9600 |
C4—H4 | 0.9300 | C12—H12C | 0.9600 |
C5—N1 | 1.338 (7) | N1—Pd1 | 2.052 (5) |
C5—C6 | 1.451 (8) | N2—O1 | 1.269 (6) |
C6—N3 | 1.289 (7) | N3—Pd1 | 2.037 (5) |
C6—N2 | 1.370 (8) | Cl1—Pd1 | 2.280 (2) |
C7—N2 | 1.476 (8) | Cl2—Pd1 | 2.273 (2) |
C7—C9 | 1.520 (11) | O1S—C2Si | 1.370 (10) |
C7—C10 | 1.524 (10) | O1S—C2S | 1.370 (10) |
C7—C8 | 1.576 (9) | C2S—C3S | 1.433 (13) |
C8—N3 | 1.505 (8) | C2S—H2S1 | 0.9700 |
C8—C12 | 1.526 (9) | C2S—H2S2 | 0.9700 |
C8—C11 | 1.529 (10) | C3S—C3Si | 1.479 (18) |
C9—H9A | 0.9600 | C3S—H3S1 | 0.9700 |
C9—H9B | 0.9600 | C3S—H3S2 | 0.9700 |
C9—H9C | 0.9600 | ||
N1—C1—C2 | 122.5 (6) | H10B—C10—H10C | 109.5 |
N1—C1—H1 | 118.8 | C8—C11—H11A | 109.5 |
C2—C1—H1 | 118.8 | C8—C11—H11B | 109.5 |
C1—C2—C3 | 120.1 (7) | H11A—C11—H11B | 109.5 |
C1—C2—H2 | 120.0 | C8—C11—H11C | 109.5 |
C3—C2—H2 | 120.0 | H11A—C11—H11C | 109.5 |
C2—C3—C4 | 117.9 (6) | H11B—C11—H11C | 109.5 |
C2—C3—H3 | 121.1 | C8—C12—H12A | 109.5 |
C4—C3—H3 | 121.1 | C8—C12—H12B | 109.5 |
C3—C4—C5 | 119.4 (6) | H12A—C12—H12B | 109.5 |
C3—C4—H4 | 120.3 | C8—C12—H12C | 109.5 |
C5—C4—H4 | 120.3 | H12A—C12—H12C | 109.5 |
N1—C5—C4 | 121.5 (6) | H12B—C12—H12C | 109.5 |
N1—C5—C6 | 112.1 (5) | C1—N1—C5 | 118.6 (6) |
C4—C5—C6 | 126.3 (6) | C1—N1—Pd1 | 126.5 (4) |
N3—C6—N2 | 112.8 (5) | C5—N1—Pd1 | 114.9 (4) |
N3—C6—C5 | 120.7 (5) | O1—N2—C6 | 125.7 (5) |
N2—C6—C5 | 126.4 (5) | O1—N2—C7 | 123.5 (5) |
N2—C7—C9 | 106.0 (6) | C6—N2—C7 | 110.6 (5) |
N2—C7—C10 | 109.5 (6) | C6—N3—C8 | 110.5 (5) |
C9—C7—C10 | 110.5 (7) | C6—N3—Pd1 | 112.6 (4) |
N2—C7—C8 | 100.9 (5) | C8—N3—Pd1 | 136.0 (4) |
C9—C7—C8 | 113.9 (6) | N3—Pd1—N1 | 79.58 (19) |
C10—C7—C8 | 115.1 (6) | N3—Pd1—Cl2 | 173.28 (15) |
N3—C8—C12 | 106.3 (5) | N1—Pd1—Cl2 | 93.72 (14) |
N3—C8—C11 | 109.4 (5) | N3—Pd1—Cl1 | 98.44 (15) |
C12—C8—C11 | 110.5 (5) | N1—Pd1—Cl1 | 176.70 (15) |
N3—C8—C7 | 102.5 (4) | Cl2—Pd1—Cl1 | 88.28 (8) |
C12—C8—C7 | 113.4 (6) | C2Si—O1S—C2S | 111.5 (11) |
C11—C8—C7 | 114.1 (6) | O1S—C2S—C3S | 107.6 (9) |
C7—C9—H9A | 109.5 | O1S—C2S—H2S1 | 110.2 |
C7—C9—H9B | 109.5 | C3S—C2S—H2S1 | 110.2 |
H9A—C9—H9B | 109.5 | O1S—C2S—H2S2 | 110.2 |
C7—C9—H9C | 109.5 | C3S—C2S—H2S2 | 110.2 |
H9A—C9—H9C | 109.5 | H2S1—C2S—H2S2 | 108.5 |
H9B—C9—H9C | 109.5 | C2S—C3S—C3Si | 105.0 (6) |
C7—C10—H10A | 109.5 | C2S—C3S—H3S1 | 110.7 |
C7—C10—H10B | 109.5 | C3Si—C3S—H3S1 | 110.7 |
H10A—C10—H10B | 109.5 | C2S—C3S—H3S2 | 110.7 |
C7—C10—H10C | 109.5 | C3Si—C3S—H3S2 | 110.7 |
H10A—C10—H10C | 109.5 | H3S1—C3S—H3S2 | 108.8 |
Symmetry code: (i) −x+1, y, −z+3/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
C4—H4···O1ii | 0.93 | 2.61 | 3.307 (8) | 132 |
C10—H10B···Cl1iii | 0.96 | 2.77 | 3.691 (7) | 160 |
Symmetry codes: (ii) −x+1, −y, −z+1; (iii) −x+1/2, y−1/2, −z+3/2. |
Experimental details
Crystal data | |
Chemical formula | [PdCl2(C12H16N3O)]·0.5C4H8O |
Mr | 431.65 |
Crystal system, space group | Monoclinic, C2/c |
Temperature (K) | 293 |
a, b, c (Å) | 19.1398 (10), 15.2061 (12), 13.8291 (10) |
β (°) | 123.415 (3) |
V (Å3) | 3359.6 (4) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 1.43 |
Crystal size (mm) | 0.7 × 0.3 × 0.3 |
Data collection | |
Diffractometer | Nonius KappaCCD diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 5707, 3065, 2049 |
Rint | 0.059 |
(sin θ/λ)max (Å−1) | 0.603 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.057, 0.152, 1.03 |
No. of reflections | 3065 |
No. of parameters | 199 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.61, −0.95 |
Computer programs: Collect (Nonius, 2000), HKL SCALEPACK (Otwinowski & Minor, 1997), HKL DENZO and SCALEPACK (Otwinowski & Minor, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997) and Mercury (Macrae et al., 2006), WinGX (Farrugia, 1999).
D—H···A | D—H | H···A | D···A | D—H···A |
C4—H4···O1i | 0.93 | 2.61 | 3.307 (8) | 132.1 |
C10—H10B···Cl1ii | 0.96 | 2.77 | 3.691 (7) | 160.2 |
Symmetry codes: (i) −x+1, −y, −z+1; (ii) −x+1/2, y−1/2, −z+3/2. |
Acknowledgements
The authors thank the Centre de Diffractomtétrie de l'Université de Rennes 1 CDiFX for the data collection.
References
Caneschi, A., Gatteschi, D. & Rey, P. (1991). Prog. Inorg. Chem. 39, 331–429. CrossRef Web of Science Google Scholar
Davis, M. S., Morokuma, K. & Kreilick, R. W. (1972). J. Am. Chem. Soc. 94, 5588–5592. CrossRef CAS Web of Science Google Scholar
Evans, D., Osborn, J. A. & Wilkinson, G. (1968). Inorg. Synth. 11, 99–101. CrossRef CAS Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838. CrossRef CAS IUCr Journals Google Scholar
Fettouhi, M., El Ali, B., Morsy, M., Golhen, S., Ouahab, L., Le Guennic, B., Saillard, J. Y., Daro, N., Sutter, J. P. & Amouyal, E. (2003). Inorg. Chem. 42, 1316–1321. Web of Science CSD CrossRef PubMed CAS Google Scholar
Li, L., Liao, D., Jiang, Z. & Yan, S. (2004). Inorg. Chim. Acta, 357, 405–410. Web of Science CSD CrossRef CAS Google Scholar
Ma, Y., Gao, D. Z., Zhang, W., Yoshimura, K., Liao, D. Z., Jiang, Z. H. & Yan, S. P. (2006). Inorg. Chim. Acta, 359, 4655–4659. Web of Science CSD CrossRef CAS Google Scholar
Ma, Y., Zhang, W., Yang, Y. O., Yoshimura, K., Liao, D. Z., Jiang, Z. H. & Yan, S. P. (2007). J. Mol. Struct. 833, 98–101. Web of Science CSD CrossRef CAS Google Scholar
Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453–457. Web of Science CrossRef CAS IUCr Journals Google Scholar
Nonius (2000). COLLECT. Nonius BV, Delft, The Netherlands. Google Scholar
Oshio, H., Ohto, A. & Ito, T. (1996). Chem. Commun. pp. 1541–1542. CSD CrossRef Web of Science Google Scholar
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307–326. New York: Academic Press. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Ueda, M., Itou, M., Okazawa, K., Mochida, T. & Mori, H. (2005). Polyhedron, 24, 2189–2193. Web of Science CSD CrossRef CAS Google Scholar
Ueda, M., Mochida, T., Itou, M., Asanagi, N. & Mori, H. (2003). Inorg. Chim. Acta, 348, 123–128. Web of Science CSD CrossRef CAS Google Scholar
Ullman, E. F. & Holm, R. H. (1970). J. Org. Chem. 35, 3623–3631. CrossRef CAS Web of Science Google Scholar
Xu, Y. H., Qu, X. N., Song, H. B., Li, L. C., Jiang, Z. H. & Liao, D. Z. (2007). Polyhedron, 26, 741–747. Web of Science CSD CrossRef CAS Google Scholar
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Organic nitronyl nitroxide radicals have attracted much attention for their magnetic properties in general and ferromagnetism in particular. Then several transition metal complexes with stable nitronyl nitroxide radical ligands have been prepared and extensively investigated (Ma et al., 2007; Xu et al., 2007; Ma et al., 2006; Ueda et al., 2005; Li et al., 2004; Ueda et al., 2003; Oshio et al., 1996; Caneschi et al., 1991). Our contribution in this field is the synthesis (see Scheme 1) and structure characterization of the title compound.
The molecular structure of the complex [Pd(IM2py)Cl2] 0.5THF(I) is shown in Fig. 1 while selected geometric parameters are given in Table 1. Focusing the coordination square of PdII, one can notice that Cl2 atom deviates significantly from the phane defined with atoms N3/N1/Pd1/Cl1 by 0.0843 (23) Å. The mean bond distance of Pd—Cl 2.277 Å is in agreement with the values observed in a similar complex while the average bond length of Pd—N 2.045 Å is slightly longer than seen previously (Fettouhi et al., 2003). Due to a chelation of the iminonitroxide radical with PdII ion, the four atoms which define the PdII coordination plane and the eight atoms which belong to both pyridyl ring and imino fragment are coplanar, the larger deviation to the plane is equal to 0.087 (5) and -0.064 (5) Å for O1 and N3 respectively. Only sp3 carbon C7 and C8 from imino and methyl carbon C9, C10, C11 and C12 deviate significantly from the mean plane.
In the packing, one can notice that intermolecular interactions shorter than the corresponding van-der-Waals radii are only observed between PdII complexes, no short contact are observed around THF molecule. Centrosymetric contacts take place between imino and pyridyl ring (O1—H4) of one neighbouring complex as well as contacts between chlorine Cl1 and H10B atom of methylene group (Table 1). These contacts yield a two-dimensional network of interacting complexes along the (101) plane (Fig. 2). Another short contact is observed between two adjacent 2-D networks thanks to a van-der-Waals interaction between two C1 atoms of pyridyl rings of two neighbouring molecules with C1—C1 3.393 (16) Å. The shortest distance between two palladium take place between ions from two adjacent planes (Pd1—Pd1 = 3.648 (2) Å), onto a plane, the shorter Pd1—Pd1 distance is 8.7834 (7) Å. THF solvent molecules are lying between two planes. A contact O1s—H1 of 2.7445 Å is observed with pyridyl ring.