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metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 64| Part 3| March 2008| Pages m487-m488
doi:10.1107/S1600536808004406

cis-Di­chlorido[4,4,5,5-tetra­methyl-2-(2-pyrid­yl)-2-imidazoline-1-ox­yl]­palladium(II) tetra­hydro­furan hemi­solvate

Sihem Badeche,a* Djamil Azzedine Rouag,a Sabrina Benmebarek,a Salah-Eddine Bouaouda and Stéphane Golhenb

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

(Received 8 February 2008; accepted 13 February 2008; online 20 February 2008)

The asymmetric unit of the title complex, [PdCl2(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 crystal structure, 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.

Related literature

For related literature, see: Caneschi et al. (1991[Caneschi, A., Gatteschi, D. & Rey, P. (1991). Prog. Inorg. Chem. 39, 331-429.]); Davis et al. (1972[Davis, M. S., Morokuma, K. & Kreilick, R. W. (1972). J. Am. Chem. Soc. 94, 5588-5592.]); Evans et al. (1968[Evans, D., Osborn, J. A. & Wilkinson, G. (1968). Inorg. Synth. 11, 99-101.]); Fettouhi et al. (2003[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.]); Li et al. (2004[Li, L., Liao, D., Jiang, Z. & Yan, S. (2004). Inorg. Chim. Acta, 357, 405-410.]); Ma et al. (2006[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.], 2007[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.]); Oshio et al. (1996[Oshio, H., Ohto, A. & Ito, T. (1996). Chem. Commun. pp. 1541-1542.]); Ueda et al. (2003[Ueda, M., Mochida, T., Itou, M., Asanagi, N. & Mori, H. (2003). Inorg. Chim. Acta, 348, 123-128.], 2005[Ueda, M., Itou, M., Okazawa, K., Mochida, T. & Mori, H. (2005). Polyhedron, 24, 2189-2193.]); Ullman & Holm (1970[Ullman, E. F. & Holm, R. H. (1970). J. Org. Chem. 35, 3623-3631.]); Xu et al. (2007[Xu, Y. H., Qu, X. N., Song, H. B., Li, L. C., Jiang, Z. H. & Liao, D. Z. (2007). Polyhedron, 26, 741-747.]).

[Scheme 1]

Experimental

Crystal data

  • [PdCl2(C12H16N3O)]·0.5C4H8O

  • Mr = 431.65

  • Monoclinic, C 2/c

  • a = 19.1398 (10) Å

  • b = 15.2061 (12) Å

  • c = 13.8291 (10) Å

  • β = 123.415 (3)°

  • V = 3359.6 (4) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 1.43 mm−1

  • T = 293 (2) K

  • 0.7 × 0.3 × 0.3 mm
Data collection

  • Nonius KappaCCD diffractometer

  • Absorption correction: none

  • 5707 measured reflections

  • 3065 independent reflections

  • 2049 reflections with I > 2σ(I)

  • Rint = 0.059
Refinement

  • R[F2 > 2σ(F2)] = 0.057

  • wR(F2) = 0.152

  • S = 1.03

  • 3065 reflections

  • 199 parameters

  • H-atom parameters constrained

  • Δρmax = 0.61 e Å−3

  • Δρmin = −0.95 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
C4—H4⋯O1i 0.93 2.61 3.307 (8) 132
C10—H10B⋯Cl1ii 0.96 2.77 3.691 (7) 160
Symmetry codes: (i) -x+1, -y, -z+1; (ii) [-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{3\over 2}}].

Data collection: COLLECT (Nonius, 2000[Nonius (2000). COLLECT. Nonius BV, Delft, The Netherlands.]); cell refinement: HKL SCALEPACK (Otwinowski & Minor, 1997[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.]); data reduction: HKL DENZO (Otwinowski & Minor, 1997[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.]) and SCALEPACK; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]) and Mercury (Macrae et al., 2006[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.]); software used to prepare material for publication: WinGX (Farrugia, 1999[Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.]).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808004406/dn2318sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808004406/dn2318Isup2.hkl

checkCIF report


Comment top

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.

Related literature top

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 top

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).

Refinement top

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.

Computing details top

Data collection: Collect (Nonius, 2000); cell refinement: 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).

Figures top
[Figure 1] Fig. 1. An ORTEP drawing of title compound showing 30% probability displacement ellipsoids and the atom-numbering scheme. The labels of the H atoms have been omitted for clarity. [Symmetry codes: (i) -x + 1, y, -z + 1.5]
[Figure 2] Fig. 2. Partial packing view showing the formation of a two-dimensionnal network through C—H···O and C—H···Cl intermolecular interactions. H bonds are shown as dashed lines. H atoms not involved in hydrogen bonding have been omitted for clarity. [Symmetry codes: (i) -x –+1, -y, -z + 1; (ii) 1/2 - x, y + 1/2, 3/2 - z]
[Figure 3] Fig. 3. The formation of the title compound.
cis-Dichlorido[4,4,5,5-tetramethyl-2-(2-pyridyl)-2-imidazoline-1- oxyl]palladium(II) tetrahydrofuran hemisolvate top
Crystal data top
[PdCl2(C12H16N3O)]·0.5C4H8OF(000) = 1736
Mr = 431.65Dx = 1.707 Mg m−3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 2981 reflections
a = 19.1398 (10) Åθ = 2.6–25.4°
b = 15.2061 (12) ŵ = 1.43 mm−1
c = 13.8291 (10) ÅT = 293 K
β = 123.415 (3)°Thick plate, brown
V = 3359.6 (4) Å30.7 × 0.3 × 0.3 mm
Z = 8
Data collection top
Nonius KappaCCD
diffractometer		2049 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.059
Graphite monochromatorθmax = 25.4°, θmin = 3.0°
ϕ and ω scansh = −22→22
5707 measured reflectionsk = −17→18
3065 independent reflectionsl = −16→16
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.057Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.152H-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 parametersΔρmax = 0.61 e Å−3
0 restraintsΔρmin = −0.95 e Å−3
Crystal data top
[PdCl2(C12H16N3O)]·0.5C4H8OV = 3359.6 (4) Å3
Mr = 431.65Z = 8
Monoclinic, C2/cMo Kα radiation
a = 19.1398 (10) ŵ = 1.43 mm−1
b = 15.2061 (12) ÅT = 293 K
c = 13.8291 (10) Å0.7 × 0.3 × 0.3 mm
β = 123.415 (3)°
Data collection top
Nonius KappaCCD
diffractometer		2049 reflections with I > 2σ(I)
5707 measured reflectionsRint = 0.059
3065 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0570 restraints
wR(F2) = 0.152H-atom parameters constrained
S = 1.03Δρmax = 0.61 e Å−3
3065 reflectionsΔρmin = −0.95 e Å−3
199 parameters
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.4332 (5)0.2973 (4)0.6038 (6)0.0604 (18)
H10.41960.35110.62140.073*
C20.4905 (5)0.2955 (5)0.5741 (8)0.072 (2)
H20.51540.34750.57230.087*
C30.5113 (5)0.2173 (5)0.5470 (6)0.0603 (18)
H30.54970.21510.52580.072*
C40.4733 (5)0.1419 (4)0.5520 (6)0.0558 (18)
H40.48510.08770.53300.067*
C50.4172 (4)0.1475 (4)0.5858 (5)0.0443 (14)
C60.3741 (4)0.0747 (4)0.5988 (5)0.0445 (14)
C70.3264 (5)−0.0669 (4)0.6000 (6)0.0560 (17)
C80.2934 (4)0.0028 (4)0.6501 (6)0.0498 (16)
C90.2604 (6)−0.0980 (6)0.4783 (7)0.081 (2)
H9A0.2328−0.04790.42940.122*
H9B0.2201−0.13390.48060.122*
H9C0.2867−0.13170.44800.122*
C100.3725 (5)−0.1451 (5)0.6789 (8)0.078 (2)
H10A0.3899−0.18430.64150.117*
H10B0.3359−0.17570.69460.117*
H10C0.4208−0.12460.75030.117*
C110.1983 (5)0.0032 (5)0.5897 (7)0.076 (2)
H11A0.18240.05010.62020.114*
H11B0.1805−0.05200.60300.114*
H11C0.17230.01160.50800.114*
C120.3364 (5)−0.0032 (5)0.7811 (6)0.067 (2)
H12A0.3951−0.01430.81670.101*
H12B0.3121−0.05020.79940.101*
H12C0.32920.05130.80980.101*
N10.3961 (3)0.2250 (3)0.6084 (5)0.0470 (12)
N20.3857 (4)−0.0129 (3)0.5888 (5)0.0512 (13)
N30.3211 (3)0.0884 (3)0.6270 (5)0.0509 (13)
O10.4363 (3)−0.0447 (3)0.5657 (5)0.0687 (14)
Cl10.21890 (16)0.20499 (14)0.7093 (2)0.0865 (7)
Cl20.30744 (14)0.36626 (13)0.67356 (19)0.0761 (6)
Pd10.30983 (3)0.21827 (3)0.65241 (5)0.0534 (2)
O1S0.50000.4980 (7)0.75000.177 (7)
C2S0.5251 (8)0.5487 (7)0.6926 (10)0.108 (3)
H2S10.49490.53190.61160.130*
H2S20.58450.54080.72630.130*
C3S0.5078 (9)0.6386 (6)0.7032 (11)0.118 (4)
H3S10.45900.65950.63120.142*
H3S20.55520.67580.72350.142*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.069 (5)0.050 (4)0.066 (5)0.003 (3)0.040 (4)−0.004 (3)
C20.077 (6)0.059 (5)0.091 (6)−0.023 (4)0.052 (5)−0.002 (4)
C30.060 (4)0.068 (5)0.065 (5)−0.006 (4)0.041 (4)0.000 (4)
C40.071 (5)0.053 (4)0.064 (5)0.003 (3)0.050 (4)0.003 (3)
C50.050 (4)0.045 (3)0.039 (3)−0.002 (3)0.026 (3)−0.002 (3)
C60.050 (4)0.046 (3)0.048 (4)0.004 (3)0.034 (3)0.003 (3)
C70.068 (5)0.046 (3)0.073 (5)−0.006 (3)0.050 (4)0.001 (3)
C80.050 (4)0.053 (4)0.054 (4)0.000 (3)0.034 (4)0.008 (3)
C90.095 (7)0.079 (5)0.083 (6)−0.018 (5)0.057 (6)−0.017 (5)
C100.100 (7)0.060 (5)0.105 (7)0.009 (4)0.075 (6)0.022 (4)
C110.061 (5)0.085 (6)0.091 (6)−0.010 (4)0.048 (5)0.000 (5)
C120.074 (5)0.078 (5)0.060 (5)−0.003 (4)0.044 (4)0.005 (4)
N10.051 (3)0.043 (3)0.049 (3)−0.002 (2)0.029 (3)0.002 (2)
N20.059 (3)0.043 (3)0.067 (4)0.006 (3)0.044 (3)0.006 (2)
N30.056 (3)0.052 (3)0.057 (3)0.006 (3)0.039 (3)0.005 (2)
O10.083 (4)0.052 (3)0.103 (4)0.014 (3)0.072 (4)0.004 (3)
Cl10.0970 (17)0.0960 (15)0.1066 (18)0.0216 (13)0.0814 (16)0.0034 (12)
Cl20.0873 (15)0.0578 (10)0.0865 (15)0.0200 (10)0.0499 (13)−0.0037 (9)
Pd10.0586 (4)0.0552 (3)0.0549 (4)0.0116 (3)0.0366 (3)−0.0002 (2)
O1S0.249 (17)0.068 (6)0.35 (2)0.0000.246 (18)0.000
C2S0.116 (9)0.094 (7)0.134 (10)−0.007 (6)0.081 (8)−0.014 (7)
C3S0.178 (12)0.073 (6)0.142 (10)−0.025 (7)0.113 (10)−0.009 (6)
Geometric parameters (Å, º) top
C1—N11.329 (8)C10—H10A0.9600
C1—C21.367 (11)C10—H10B0.9600
C1—H10.9300C10—H10C0.9600
C2—C31.370 (10)C11—H11A0.9600
C2—H20.9300C11—H11B0.9600
C3—C41.381 (9)C11—H11C0.9600
C3—H30.9300C12—H12A0.9600
C4—C51.388 (8)C12—H12B0.9600
C4—H40.9300C12—H12C0.9600
C5—N11.338 (7)N1—Pd12.052 (5)
C5—C61.451 (8)N2—O11.269 (6)
C6—N31.289 (7)N3—Pd12.037 (5)
C6—N21.370 (8)Cl1—Pd12.280 (2)
C7—N21.476 (8)Cl2—Pd12.273 (2)
C7—C91.520 (11)O1S—C2Si1.370 (10)
C7—C101.524 (10)O1S—C2S1.370 (10)
C7—C81.576 (9)C2S—C3S1.433 (13)
C8—N31.505 (8)C2S—H2S10.9700
C8—C121.526 (9)C2S—H2S20.9700
C8—C111.529 (10)C3S—C3Si1.479 (18)
C9—H9A0.9600C3S—H3S10.9700
C9—H9B0.9600C3S—H3S20.9700
C9—H9C0.9600
N1—C1—C2122.5 (6)H10B—C10—H10C109.5
N1—C1—H1118.8C8—C11—H11A109.5
C2—C1—H1118.8C8—C11—H11B109.5
C1—C2—C3120.1 (7)H11A—C11—H11B109.5
C1—C2—H2120.0C8—C11—H11C109.5
C3—C2—H2120.0H11A—C11—H11C109.5
C2—C3—C4117.9 (6)H11B—C11—H11C109.5
C2—C3—H3121.1C8—C12—H12A109.5
C4—C3—H3121.1C8—C12—H12B109.5
C3—C4—C5119.4 (6)H12A—C12—H12B109.5
C3—C4—H4120.3C8—C12—H12C109.5
C5—C4—H4120.3H12A—C12—H12C109.5
N1—C5—C4121.5 (6)H12B—C12—H12C109.5
N1—C5—C6112.1 (5)C1—N1—C5118.6 (6)
C4—C5—C6126.3 (6)C1—N1—Pd1126.5 (4)
N3—C6—N2112.8 (5)C5—N1—Pd1114.9 (4)
N3—C6—C5120.7 (5)O1—N2—C6125.7 (5)
N2—C6—C5126.4 (5)O1—N2—C7123.5 (5)
N2—C7—C9106.0 (6)C6—N2—C7110.6 (5)
N2—C7—C10109.5 (6)C6—N3—C8110.5 (5)
C9—C7—C10110.5 (7)C6—N3—Pd1112.6 (4)
N2—C7—C8100.9 (5)C8—N3—Pd1136.0 (4)
C9—C7—C8113.9 (6)N3—Pd1—N179.58 (19)
C10—C7—C8115.1 (6)N3—Pd1—Cl2173.28 (15)
N3—C8—C12106.3 (5)N1—Pd1—Cl293.72 (14)
N3—C8—C11109.4 (5)N3—Pd1—Cl198.44 (15)
C12—C8—C11110.5 (5)N1—Pd1—Cl1176.70 (15)
N3—C8—C7102.5 (4)Cl2—Pd1—Cl188.28 (8)
C12—C8—C7113.4 (6)C2Si—O1S—C2S111.5 (11)
C11—C8—C7114.1 (6)O1S—C2S—C3S107.6 (9)
C7—C9—H9A109.5O1S—C2S—H2S1110.2
C7—C9—H9B109.5C3S—C2S—H2S1110.2
H9A—C9—H9B109.5O1S—C2S—H2S2110.2
C7—C9—H9C109.5C3S—C2S—H2S2110.2
H9A—C9—H9C109.5H2S1—C2S—H2S2108.5
H9B—C9—H9C109.5C2S—C3S—C3Si105.0 (6)
C7—C10—H10A109.5C2S—C3S—H3S1110.7
C7—C10—H10B109.5C3Si—C3S—H3S1110.7
H10A—C10—H10B109.5C2S—C3S—H3S2110.7
C7—C10—H10C109.5C3Si—C3S—H3S2110.7
H10A—C10—H10C109.5H3S1—C3S—H3S2108.8
Symmetry code: (i) −x+1, y, −z+3/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C4—H4···O1ii0.932.613.307 (8)132
C10—H10B···Cl1iii0.962.773.691 (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
Mr431.65
Crystal system, space groupMonoclinic, 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)
Z8
Radiation typeMo Kα
µ (mm−1)1.43
Crystal size (mm)0.7 × 0.3 × 0.3
Data collection
DiffractometerNonius KappaCCD
diffractometer
Absorption correction–
No. of measured, independent and
observed [I > 2σ(I)] reflections		5707, 3065, 2049
Rint0.059
(sin θ/λ)max (Å−1)0.603
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.057, 0.152, 1.03
No. of reflections3065
No. of parameters199
H-atom treatmentH-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).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C4—H4···O1i0.932.613.307 (8)132.1
C10—H10B···Cl1ii0.962.773.691 (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

First citationCaneschi, A., Gatteschi, D. & Rey, P. (1991). Prog. Inorg. Chem. 39, 331–429.  CrossRef Web of Science Google Scholar
 First citationDavis, M. S., Morokuma, K. & Kreilick, R. W. (1972). J. Am. Chem. Soc. 94, 5588–5592.  CrossRef CAS Web of Science Google Scholar
 First citationEvans, D., Osborn, J. A. & Wilkinson, G. (1968). Inorg. Synth. 11, 99–101.  CrossRef CAS Google Scholar
 First citationFarrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  CrossRef IUCr Journals Google Scholar
 First citationFarrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838.  CrossRef CAS IUCr Journals Google Scholar
 First citationFettouhi, 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
 First citationLi, L., Liao, D., Jiang, Z. & Yan, S. (2004). Inorg. Chim. Acta, 357, 405–410.  Web of Science CSD CrossRef CAS Google Scholar
 First citationMa, 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
 First citationMa, 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
 First citationMacrae, 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
 First citationNonius (2000). COLLECT. Nonius BV, Delft, The Netherlands.  Google Scholar
 First citationOshio, H., Ohto, A. & Ito, T. (1996). Chem. Commun. pp. 1541–1542.  CSD CrossRef Web of Science Google Scholar
 First citationOtwinowski, 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
 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationUeda, M., Itou, M., Okazawa, K., Mochida, T. & Mori, H. (2005). Polyhedron, 24, 2189–2193.  Web of Science CSD CrossRef CAS Google Scholar
 First citationUeda, M., Mochida, T., Itou, M., Asanagi, N. & Mori, H. (2003). Inorg. Chim. Acta, 348, 123–128.  Web of Science CSD CrossRef CAS Google Scholar
 First citationUllman, E. F. & Holm, R. H. (1970). J. Org. Chem. 35, 3623–3631.  CrossRef CAS Web of Science Google Scholar
 First citationXu, 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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ISSN: 2056-9890
Volume 64| Part 3| March 2008| Pages m487-m488
doi:10.1107/S1600536808004406
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