Dichlorido[1-(2,6-dimethyl­phenyl­imino)-1,2-diphenyl­propan-2-ol-κ2 N,O]palladium(II) methanol monosolvate

Feng-Shou Liu; Ying-Tang Huang; Dong-Sheng Shen; Hua-Gang Yao

doi:10.1107/S1600536811037986

. 2011 Sep 30;67(Pt 10):m1435. doi: 10.1107/S1600536811037986

Dichlorido[1-(2,6-dimethylphenylimino)-1,2-diphenylpropan-2-ol-κ² N,O]palladium(II) methanol monosolvate

Feng-Shou Liu ^a, Ying-Tang Huang ^a, Dong-Sheng Shen ^a, Hua-Gang Yao ^a,^*

PMCID: PMC3201399 PMID: 22065642

Abstract

The title compound, [PdCl₂(C₂₃H₂₃NO)]·CH₃OH, was obtained by the reaction of 1-(2,6-dimethylphenylimino)-1,2-diphenylpropan-2-ol and palladium chloride in methanol. The Pd atom is four-coordinated by the O atom of a tertiary alcohol, the imine N atom of the hydroxylimine part of the bidentate ligand and by two chloride ions, forming a nearly square-planar geometry. The complex molecule and the uncoordinated methanol molecule are connected via an O—H⋯O hydrogen bond.

Related literature

For transition metal complexes of (N,O)-bidentate ligands, see: Skrolkhod et al. (2002 ▶); Macchioni et al. (2002 ▶); Binotti et al. (2004 ▶); Zuccaccia et al. (2006 ▶). Complexes with group IV metals with (N,O)-bidentate ligands, which form six-membered rings, have been widely used in the production of polyethylene with high molecular weight and relative narrow molecular weight distribution, see: Jia & Jin (2009 ▶); Mu et al. (2009 ▶). For the use of palladium complexes in Suzuki–Miyaura cross-coupling reactions, see: Lai et al. (2005 ▶).

Experimental

Crystal data

[PdCl₂(C₂₃H₂₃NO)]·CH₄O
M _r = 538.79
Monoclinic,
a = 10.943 (3) Å
b = 19.770 (6) Å
c = 14.230 (3) Å
β = 129.232 (13)°
V = 2384.6 (11) Å³
Z = 4
Mo Kα radiation
μ = 1.02 mm⁻¹
T = 296 K
0.25 × 0.20 × 0.10 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2001 ▶) T _min = 0.779, T _max = 0.901
35358 measured reflections
4166 independent reflections
3418 reflections with I > 2σ(I)
R _int = 0.036

Refinement

R[F ² > 2σ(F ²)] = 0.042
wR(F ²) = 0.082
S = 1.01
4166 reflections
280 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.50 e Å⁻³
Δρ_min = −0.42 e Å⁻³

Data collection: APEX2 (Bruker, 2001 ▶); cell refinement: SAINT-Plus (Bruker, 2001 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811037986/kp2349sup1.cif

e-67-m1435-sup1.cif^{(20.1KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811037986/kp2349Isup2.hkl

e-67-m1435-Isup2.hkl^{(204.2KB, hkl)}

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

Table 1. Selected bond lengths (Å).

Pd1—O1	2.019 (3)
Pd1—N1	2.032 (3)
Pd1—Cl1	2.2588 (13)
Pd1—Cl2	2.2859 (13)

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

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H7⋯O2ⁱ	0.76 (6)	1.80 (6)	2.535 (5)	164 (7)

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Symmetry code: (i) Inline graphic .

Acknowledgments

We acknowledge the National Natural Science Foundation of China (No. 21004014) and the Foundation for Distinguished Young Talents in Higher Education of Guangdong (No. LYM10091) for financial support.

supplementary crystallographic information

Comment

Recently, the bidentate (N, O) ligand such as salicylaldimine and hydroxylimine have drawn much attention owing to their valuable applications in the fields of catalysis. These bidentate ligands can be modified by tuning the substituents. Therefore, different steric and electronic properties are achieved easily. Various transition metal complexes (Skrolkhod et al. 2002; Macchioni et al. 2002; Binotti et al. 2004; Zuccaccia et al. 2006) have been developed. Especially, complexes with metals of the group IV containing (N, O) ligands have been widely used to produce polyethylene with high molecular weight and relative narrow molecular weight distribution (Mu et al. 2009; Jia et al. 2009). Moreover, the palladium complexes also have been applied for Suzuki-Miyaura cross-coupling reaction (Lai et al. 2005). We report herein on the synthesis and structure of the title compound. The palladium atom is four-coordinated by the oxgen atom o a tertiary alcohol and imine nitrogen atom of the bidentate hydroxylimine ligand, and by the two chloride ions, forming a nearly square-planar geometry (Fig. 1, Table 1). The solid-state structure showes a noncentrosymmetric palladium complex with one uncoordinated methanol solvated molecule. The complex molecule and the uncoordinated methanol molecule are connected via O—H···O hydrogen bond (Table 2).

Experimental

A 100 ml round-bottle was charged with palladium chloride (0.177 g, 1 mmol), 1-(2,6-dimethylphenylimino)-1,2-diphenylpropan-2-ol (0.329 g, 1 mmol), and methanol (20 mL). After the mixture was stirred for 24 h at room temperature, the methanol was removed under reduced pressure. The red crystals suitable for X-ray diffraction wwere prepared by slow evaporation of a solution of the title compound in methanol at room temperature.