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Volume 69 
Part 5 
Pages m238-m239  
May 2013  

Received 13 March 2013
Accepted 26 March 2013
Online 5 April 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.005 Å
R = 0.038
wR = 0.105
Data-to-parameter ratio = 18.0
Details
Open access

Dichlorido{2,6-diisopropyl-N-[(S)-pyrrolidin-2-ylmethyl]aniline-[kappa]2N,N'}palladium(II)

aDepartment of Chemistry, Kyungpook National University, Taegu 702-701, Republic of Korea
Correspondence e-mail: jeongjh@knu.ac.kr

In the title compound, [PdCl2(C17H28N2)], the PdII atom displays a square-planar coordination involving two N atoms of a 2,6-diisopropyl-N-[(S)-pyrrolidin-2-ylmethyl]aniline ligand and two chloride ligands, with a deviation of 0.090 (1) Å for the PdII atom from the best plane. The absolute configuration of the chiral C atom of the pyrrolidine ring is S, which induces R configurations at the two N atoms of the aniline ligand. Optical isomerism arising from the chelate five-membered ring is configured as [delta]. The Pd-N bond lengths are 2.040 (3) and 2.072 (2) Å, and the Pd-Cl bond lengths are 2.3055 (8) and 2.3160 (8) Å. In the crystal, pairs of N-H...Cl hydrogen bonds link molecules into discrete dimers.

Related literature

For background to the use of palladium complexes bearing enantiopure ligands in asymmetric synthesis, see: Sodeoka & Hamashima (2006[Sodeoka, M. & Hamashima, Y. (2006). Pure Appl. Chem. 78, 477-494.]); Quintard et al. (2008[Quintard, A., Bournaud, C. & Alexakis, A. (2008). Chem. Eur. J. 14, 7504-7507.]); Tan et al. (2009[Tan, B., Zeng, X., Lu, Y., Chua, P. J. & Zhong, G. (2009). Org. Lett. 11, 1927-1930.]) and as anticancer drugs, see: Barnham et al. (1994[Barnham, K. J., Djuran, M. I., Frey, U., Mazid, M. A. & Sadler, P. J. (1994). J. Chem. Soc. Chem. Commun. pp. 65-66.]). For the synthesis of the 2,6-diisopropyl-N-[(S)-pyrrolidin-2-ylmethyl]aniline ligand, see: Shifeng et al. (2010[Shifeng, M., Jinjin, B., Jin, Y. & Yawen, Z. (2010). Chirality, 22, 855-862.]). For related structures, see: Rafii et al. (2007[Rafii, E., Dassonneville, B. & Heumann, A. (2007). Chem. Commun. pp. 583-585.]). For a description of the Cambridge Structural Database, see: Allen et al. (2002[Allen, F. H. (2002). Acta Cryst. B58, 380-388.]).

[Scheme 1]

Experimental

Crystal data
  • [PdCl2(C17H28N2)]

  • Mr = 437.71

  • Monoclinic, C 2/c

  • a = 24.287 (3) Å

  • b = 8.6534 (12) Å

  • c = 18.355 (2) Å

  • [beta] = 94.851 (9)°

  • V = 3843.7 (8) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 1.24 mm-1

  • T = 293 K

  • 0.45 × 0.40 × 0.40 mm

Data collection
  • Enraf-Nonius CAD-4 four-circle diffractometer

  • Absorption correction: [psi] scan (ABSCALC; McArdle & Daly, 1999[McArdle, P. & Daly, P. (1999). ABSCALC. National University of Ireland, Galway, Ireland.]) Tmin = 0.578, Tmax = 0.608

  • 3790 measured reflections

  • 3580 independent reflections

  • 3089 reflections with I > 2[sigma](I)

  • Rint = 0.018

  • 3 standard reflections every 60 min intensity decay: 0.2%

Refinement
  • R[F2 > 2[sigma](F2)] = 0.038

  • wR(F2) = 0.105

  • S = 1.08

  • 3580 reflections

  • 199 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 1.33 e Å-3

  • [Delta][rho]min = -1.56 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1...Cl2i 0.86 2.47 3.283 (3) 158
N2-H2...Cl1i 0.86 2.68 3.410 (3) 144
Symmetry code: (i) [-x+{\script{3\over 2}}, -y+{\script{3\over 2}}, -z+2].

Data collection: CAD-4 Software (Enraf-Nonius, 1989[Enraf-Nonius (1989). CAD-4 Software. Enraf-Nonius, Delft, Netherland.]); cell refinement: CAD-4 Software; data reduction: XCAD (McArdle, 1999[McArdle, P. (1999). XCAD. National University of Ireland, Galway, Ireland.]); 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: ORTEPIII (Burnett & Johnson, 1996[Burnett, M. N. & Johnson, C. K. (1996). ORTEPIII. Report ORNL-6895. Oak Ridge National Laboratory. Tennessee, USA.]); software used to prepare material for publication: SHELXL97.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: FK2069 ).


Acknowledgements

This research was supported by the Kyungpook National University Research Fund, 2012.

References

Allen, F. H. (2002). Acta Cryst. B58, 380-388.  [ISI] [CrossRef] [details]
Barnham, K. J., Djuran, M. I., Frey, U., Mazid, M. A. & Sadler, P. J. (1994). J. Chem. Soc. Chem. Commun. pp. 65-66.  [CrossRef] [ISI]
Burnett, M. N. & Johnson, C. K. (1996). ORTEPIII. Report ORNL-6895. Oak Ridge National Laboratory. Tennessee, USA.
Enraf-Nonius (1989). CAD-4 Software. Enraf-Nonius, Delft, Netherland.
McArdle, P. (1999). XCAD. National University of Ireland, Galway, Ireland.
McArdle, P. & Daly, P. (1999). ABSCALC. National University of Ireland, Galway, Ireland.
Quintard, A., Bournaud, C. & Alexakis, A. (2008). Chem. Eur. J. 14, 7504-7507.  [CrossRef] [PubMed] [ChemPort]
Rafii, E., Dassonneville, B. & Heumann, A. (2007). Chem. Commun. pp. 583-585.  [CSD] [CrossRef]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Shifeng, M., Jinjin, B., Jin, Y. & Yawen, Z. (2010). Chirality, 22, 855-862.  [ISI] [PubMed]
Sodeoka, M. & Hamashima, Y. (2006). Pure Appl. Chem. 78, 477-494.  [ISI] [CrossRef] [ChemPort]
Tan, B., Zeng, X., Lu, Y., Chua, P. J. & Zhong, G. (2009). Org. Lett. 11, 1927-1930.  [ISI] [CSD] [CrossRef] [PubMed] [ChemPort]


Acta Cryst (2013). E69, m238-m239   [ doi:10.1107/S1600536813008271 ]

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