Bis[2-phenyl-1-(phenyl­iminio)isoindo­line] di-μ-chlorido-bis­[dichloridopalladate(II)] benzene disolvate

Jackson M Chitanda; J Wilson Quail; Stephen R Foley

doi:10.1107/S1600536808017005

. 2008 Jun 13;64(Pt 7):m907–m908. doi: 10.1107/S1600536808017005

Bis[2-phenyl-1-(phenyliminio)isoindoline] di-μ-chlorido-bis[dichloridopalladate(II)] benzene disolvate

Jackson M Chitanda ^a, J Wilson Quail ^b, Stephen R Foley ^a,^*

PMCID: PMC2961759 PMID: 21202770

Abstract

In the title compound, (C₂₀H₁₇N₂)₂[Pd₂Cl₆]·2C₆H₆, the dichloride-bridged [Pd₂Cl₆]²⁻ anion lies across an inversion center with each Pd^II ion in a slightly distorted square-planar environment. In the crystal structure, two cations and an anion are connected via N—H⋯Cl hydrogen bonds between the NH groups of the iminioisoindoline cations and terminal Cl atoms of a hexachloridodipalladate(II) anion. The Pd—Cl distance of the terminal chloride engaged in hydrogen bonding is slightly longer than the Pd—Cl distance of the adjacent terminal chloride which is not involved in hydrogen bonding.

Related literature

For related literature, see: Bartczak et al. (2001 ▶); Chitanda et al. (2008 ▶); Fábry et al. (2004 ▶); Lassahn et al. (2003 ▶); Ojwach et al. (2007 ▶); Schupp et al. (2001 ▶); Yang et al. (2008 ▶).

Experimental

Crystal data

(C₂₀H₁₇N₂)₂[Pd₂Cl₆]·2C₆H₆
M _r = 1152.46
Triclinic,
a = 9.5457 (3) Å
b = 9.9754 (3) Å
c = 14.8002 (5) Å
α = 74.270 (2)°
β = 80.615 (2)°
γ = 63.228 (2)°
V = 1209.74 (7) Å³
Z = 1
Mo Kα radiation
μ = 1.11 mm⁻¹
T = 173 (2) K
0.22 × 0.18 × 0.05 mm

Data collection

Bruker–Nonius KappaCCD diffractometer
Absorption correction: ψ scan (SHELXTL; Sheldrick, 2008 ▶) T _min = 0.791, T _max = 0.946
18458 measured reflections
6458 independent reflections
5322 reflections with I > 2σ(I)
R _int = 0.038

Refinement

R[F ² > 2σ(F ²)] = 0.039
wR(F ²) = 0.094
S = 1.04
6458 reflections
290 parameters
H-atom parameters constrained
Δρ_max = 0.82 e Å⁻³
Δρ_min = −0.94 e Å⁻³

Data collection: COLLECT (Nonius, 1998 ▶); cell refinement: SCALEPACK (Otwinowski & Minor, 1997 ▶); data reduction: DENZO (Otwinowski & Minor 1997 ▶) and SCALEPACK; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808017005/lh2628sup1.cif

e-64-0m907-sup1.cif^{(22.7KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808017005/lh2628Isup2.hkl

e-64-0m907-Isup2.hkl^{(316.1KB, hkl)}

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

Table 1. Selected geometric parameters (Å, °).

Pd1—Cl2	2.2635 (7)
Pd1—Cl1	2.2929 (7)
Pd1—Cl3ⁱ	2.3292 (7)
Pd1—Cl3	2.3374 (7)

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Cl2—Pd1—Cl1	91.32 (3)
Cl2—Pd1—Cl3ⁱ	91.00 (3)
Cl1—Pd1—Cl3ⁱ	177.33 (3)
Cl2—Pd1—Cl3	176.86 (3)
Cl1—Pd1—Cl3	91.47 (3)
Cl3ⁱ—Pd1—Cl3	86.25 (3)

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Symmetry code: (i) Inline graphic .

Table 2. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯Cl1	0.88	2.37	3.242 (2)	171

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Symmetry codes: .

Acknowledgments

Financial assistance for this project was provided by the Natural Sciences and Engineering Research Council of Canada (NSERC) for an operating grant to SRF, and by the Canadian Government through the Commonwealth Scholarship fund for JMC.

supplementary crystallographic information

Comment

As part of the ongoing research in our laboratory directed at the synthesis of substituted palladacycles incorporating iminoisoindolines (Chitanda et al., 2008), the title compound, I, was obtained by reaction of 1-phenylimino-2-phenylisoindoline with dichloropalladium(II) in the presence of HCl. The bis-iminoisoindolinium hexachlorodipalladate complex crystallizes with two molecules of benzene in the unit cell of the triclinic space group P1. The crystal structure of I is stabilized by a system of intermolecular hydrogen bonds between the imine NH atoms of the iminoisoindolinium cation and the termininal chloride atoms in the hexachlorodipalladate(II) anion. The Pd₂Cl₆^2- anion lies across an inversion center and has the expected planar dichloro-bridged structure with the Pd—Cl distance of the terminal chloride engaged in hydrogen bonding being slightly longer at 2.2929 (7)Å than the Pd—Cl distance of the adjacent terminal chloride at 2.2635 (7)Å which does not show any H-bonding. In previously reported structures incorporating a Pd₂Cl₆^2- anion, the anion most often lies across an inversion center (Bartczak et al., 2001; Fábry et al., 2004; Lassahn et al., 2003; Ojwach et al., 2007; Schupp et al., 2001; Yang et al., 2008). The molecular structure and packing of the title compound is shown in Figs. 1 and 2.

Experimental

The title compound was synthesized by reaction of 1-phenylimino-2- phenylisoindoline with dichloropalladium(II) in the presence of HCl in dichloromethane. Single crystals were obtained by slow evaporation from a benzene solution at ambient temperature.