Bis{benzyl 3-[(1H-indol-3-yl)methyl­idene]dithio­carbazato-κ2 N 3,S}palladium(II) N,N-dimethyl­formamide disolvate

Hamid Khaledi; Hapipah Mohd Ali

doi:10.1107/S1600536810051780

. 2010 Dec 15;67(Pt 1):m84. doi: 10.1107/S1600536810051780

Bis{benzyl 3-[(1H-indol-3-yl)methylidene]dithiocarbazato-κ² N ³,S}palladium(II) N,N-dimethylformamide disolvate

Hamid Khaledi ^a,^*, Hapipah Mohd Ali ^a

PMCID: PMC3050367 PMID: 21522600

Abstract

In the title compound, [Pd(C₁₇H₁₄N₃S₂)₂]·2C₃H₇NO, the deprotonated Schiff base ligand acts as an N,S-bidentate chelate, forming a five-membered ring with the metal atom. The Pd^II ion, located on an inversion center, is four-coordinated by two of the Schiff base ligands in a square-planar geometry. In the crystal, the indolic NH groups are bonded to the dimethylformamide (DMF) solvent molecules via an N—H⋯O interaction. In addition, C—H⋯S interactions are observed.

Related literature

For the crystal structure of the ligand, see: Khaledi et al. (2008 ▶). For the isotypic Cu(II) analog, see: Khaledi et al. (2009 ▶). For the Pd^II complex of the acetone Schiff base of S-methyldithiocarbazate, see: Ali et al. (2002 ▶).

Experimental

Crystal data

[Pd(C₁₇H₁₄N₃S₂)₂]·2C₃H₇NO
M _r = 901.46
Monoclinic,
a = 10.509 (4) Å
b = 20.320 (7) Å
c = 10.925 (4) Å
β = 117.577 (5)°
V = 2067.8 (12) Å³
Z = 2
Mo Kα radiation
μ = 0.70 mm⁻¹
T = 296 K
0.30 × 0.15 × 0.03 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.818, T _max = 0.979
11353 measured reflections
4486 independent reflections
3411 reflections with I > 2σ(I)
R _int = 0.024

Refinement

R[F ² > 2σ(F ²)] = 0.030
wR(F ²) = 0.074
S = 1.02
4486 reflections
255 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.27 e Å⁻³
Δρ_min = −0.31 e Å⁻³

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: X-SEED (Barbour, 2001 ▶); software used to prepare material for publication: SHELXL97 and publCIF (Westrip, 2010 ▶).

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810051780/pv2368sup1.cif

e-67-00m84-sup1.cif^{(19.1KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810051780/pv2368Isup2.hkl

e-67-00m84-Isup2.hkl^{(219.8KB, hkl)}

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

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1	0.84 (2)	1.91 (2)	2.749 (3)	174 (3)
C9—H9⋯S1ⁱ	0.93	2.60	3.279 (2)	130

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Symmetry code: (i) Inline graphic .

Acknowledgments

The authors thank University of Malaya for funding this study (UMRG grant RG024/09BIO).

supplementary crystallographic information

Comment

The title compound is isostructural with the Cu^II complex of the Schiff base ligand (Khaledi et al., 2009). The palladium(II) ion is four-coordinated by two azomethine nitrogen and two thioamide sulfur atoms in a trans-square planar geometry. It has been suggested that the square planar geometry of the Schiff bases of S-alkyldithiocarbazate is trans when they are derived from aldehydes, whereas the ketone derivatives show cis geometry (Ali et al., 2002). Similar to the analogous Cu^II complex, the indole amino groups in the present structure are hydrogen bonded to the co-crystallized DMF molecules. Moreover, non-classical hydrogen bonds, C—H···N, C—H···O and C—H···S, are observed in the structure.

Experimental

The Schiff base ligand was prepared as reported previously (Khaledi et al., 2008). A solution of palladium(II) acetate (0.224 g, 1 mmol) in ethanol (30 ml) was added to an ethanolic solution (30 ml) of the ligand (0.65 g, 2 mmol) containing a few drops of triethylamine. The mixture was refluxed for an hour, then cooled to room temperature. The resulting brown solid was filtered, washed with cold ethanol and dried over siliga-gel. The title crystals were obtained by slow evaporation of a solution of the solid in DMF.