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Volume 69 
Part 10 
Pages m528-m529  
October 2013  

Received 1 July 2013
Accepted 15 August 2013
Online 4 September 2013

Key indicators
Single-crystal X-ray study
T = 173 K
Mean [sigma](C-C) = 0.005 Å
R = 0.049
wR = 0.128
Data-to-parameter ratio = 26.5
Details
Open access

{2-[1-(2-Methoxy-6-oxidophenyl-[kappa]O6)ethylidene]-N-methylhydrazinecarbothioamidato-[kappa]2N2,S}(triphenylphosphane-[kappa]P)palladium(II) ethanol monosolvate

aDepartment of Chemistry, Keene State College, 229 Main Street, Keene, NH 03435-2001, USA
Correspondence e-mail: jjasinski@keene.edu

In the title compound, [Pd(C11H13N3O2S)(C18H15P)]·C2H5OH, the PdII atom is tetracoordinated in a slightly distorted square-planar environment by three donor atoms (NOS) from a thiosemicarbazonate ligand, forming five- and six-membered chelate rings, and a P atom from a neutral triphenylphosphane group. The five-membered ring adopts a distorted envelope conformation with PdII as the flap atom, while the six-membered ring forms a slightly twisted screw-boat conformation. A slightly distorted screw-boat form of a methoxyphenyl group is fused to the six-membered ring. Weak C-H...O interactions form dimers in the asymmetric unit and along [001] which help to stabilize the crystal packing.

Related literature

For multiple binding modes of thiosemicarbazones, see: Lobana et al. (2009[Lobana, T. S., Sharma, R., Bawa, G. & Khanna, S. (2009). Coord. Chem. Rev. 253, 977-1055.]). For the synthesis of thiosemicarbazone complexes, see: Lobana et al. (2012[Lobana, T. S., Kumari, P., Bawa, G., Hundal, G., Butcher, R. J., Fernandez, F. J., Jasinski, J. P. & Golen, J. A. (2012). Z. Anorg. Allg. Chem. 638, 804-810.]). For palladium thiosemicarbazone complexes, see: Chellan et al. (2010[Chellan, P., Shunmoogam-Gounden, N., Hendricks, D. T., Gut, J., Rosenthal, P. J., Lategan, C., Smith, P. J., Chibale, K. & Smith, G. S. (2010). Eur. J. Inorg. Chem. pp. 3520-3528.]). For comparison with the anti-cancer drug cisplatin, see: Halder et al. (2008[Halder, S., Peng, S.-M., Lee, G.-H., Chatterjee, T., Mukherjee, A., Dutta, S., Sanyal, U. & Bhattacharya, S. (2008). New J. Chem. 32, 105-114.]). For puckering parameters, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]). For standard bond lengths, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]).

[Scheme 1]

Experimental

Crystal data
  • [Pd(C11H13N3O2S)(C18H15P)]·C2H6O

  • Mr = 666.04

  • Triclinic, [P \overline 1]

  • a = 8.0294 (6) Å

  • b = 12.0187 (6) Å

  • c = 16.2151 (8) Å

  • [alpha] = 105.764 (4)°

  • [beta] = 100.835 (5)°

  • [gamma] = 94.965 (5)°

  • V = 1463.33 (15) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.80 mm-1

  • T = 173 K

  • 0.28 × 0.12 × 0.06 mm

Data collection
  • Agilent Xcalibur (Eos, Gemini) diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO and CrysAlis RED; Agilent, 2012[Agilent (2012). CrysAlis PRO and CrysAlis RED. Agilent Technologies, Yarnton, England.]) Tmin = 0.744, Tmax = 1.000

  • 17885 measured reflections

  • 9710 independent reflections

  • 8289 reflections with I > 2[sigma](I)

  • Rint = 0.049

Refinement
  • R[F2 > 2[sigma](F2)] = 0.049

  • wR(F2) = 0.128

  • S = 1.10

  • 9710 reflections

  • 366 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 2.09 e Å-3

  • [Delta][rho]min = -1.04 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C9-H9C...O2i 0.98 2.69 3.439 (5) 133
Symmetry code: (i) -x+1, -y+1, -z.

Data collection: CrysAlis PRO (Agilent, 2012[Agilent (2012). CrysAlis PRO and CrysAlis RED. Agilent Technologies, Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED (Agilent, 2012[Agilent (2012). CrysAlis PRO and CrysAlis RED. Agilent Technologies, Yarnton, England.]); program(s) used to solve structure: SUPERFLIP (Palatinus & Chapuis, 2007[Palatinus, L. & Chapuis, G. (2007). J. Appl. Cryst. 40, 786-790.]); program(s) used to refine structure: SHELXL2012 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: XP in SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009[Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BV2224 ).


Acknowledgements

JPJ acknowledges the NSF-MRI program (grant No. CHE-1039027) for funds to purchase the X-ray diffractometer.

References

Agilent (2012). CrysAlis PRO and CrysAlis RED. Agilent Technologies, Yarnton, England.
Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.
Chellan, P., Shunmoogam-Gounden, N., Hendricks, D. T., Gut, J., Rosenthal, P. J., Lategan, C., Smith, P. J., Chibale, K. & Smith, G. S. (2010). Eur. J. Inorg. Chem. pp. 3520-3528.  [Web of Science] [CSD] [CrossRef]
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.  [CrossRef] [ChemPort] [Web of Science]
Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Halder, S., Peng, S.-M., Lee, G.-H., Chatterjee, T., Mukherjee, A., Dutta, S., Sanyal, U. & Bhattacharya, S. (2008). New J. Chem. 32, 105-114.  [Web of Science] [CSD] [CrossRef] [ChemPort]
Lobana, T. S., Kumari, P., Bawa, G., Hundal, G., Butcher, R. J., Fernandez, F. J., Jasinski, J. P. & Golen, J. A. (2012). Z. Anorg. Allg. Chem. 638, 804-810.  [CSD] [CrossRef] [ChemPort]
Lobana, T. S., Sharma, R., Bawa, G. & Khanna, S. (2009). Coord. Chem. Rev. 253, 977-1055.  [Web of Science] [CrossRef] [ChemPort]
Palatinus, L. & Chapuis, G. (2007). J. Appl. Cryst. 40, 786-790.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]


Acta Cryst (2013). E69, m528-m529   [ doi:10.1107/S1600536813023040 ]

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