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Volume 68 
Part 12 
Pages m1476-m1477  
December 2012  

Received 25 September 2012
Accepted 6 November 2012
Online 14 November 2012

Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.004 Å
R = 0.037
wR = 0.067
Data-to-parameter ratio = 22.6
Details
Open access

cis-Dichloridobis(2-isocyanophenyl 4-methoxybenzoate)palladium(II) chloroform monosolvate

aDepartment of Chemistry, Saint-Petersburg State University, Universitetsky Pr. 26, 198504 Stary Petergof, Russian Federation, and bUniversity of Jyväskylä, Department of Chemistry, PO Box 35, 40014 University of Jyväskylä, Finland
Correspondence e-mail: matti.o.haukka@jyu.fi

In the title compound, [PdCl2(C15H11NO3)2]·CHCl3, the PdII atom adopts a slightly distorted square-planar coordination geometry composed of two Cl atoms in cis positions and two C atoms from isocyanophenyl ligands. The molecular conformation is stabilized by [pi]-[pi] stacking interactions [shortest centroid-centroid distance = 3.600 (1) Å] between substituted benzene rings of different ligands. The crystal packing is characterized by C-H...O and C-H...Cl interactions involving the chloroform solvent molecules.

Related literature

For further information on acyclic diaminocarbenes, see: Slaughter (2012[Slaughter, L. M. (2012). ACS Catal. 2, 1802-1816.]); Boyarskiy et al. (2012[Boyarskiy, V. P., Luzyanin, K. V. & Kukushkin, V. Y. (2012). Coord. Chem. Rev. 256, 2029-2056.]). For background to the Passerini reaction, see: Banfi & Riva (2005[Banfi, L. & Riva, R. (2005). Org. React. pp. 1-140.]). For novel metal-mediated coupling as a route to cyclic carbenes and aminocarbene complexes, see: Luzyanin et al. (2009a[Luzyanin, K. V., Tskhovrebov, A. G., Carias, M. C., Guedes da Silva, M. F. C., Pombeiro, A. J. L. & Kukushkin, V. Y. (2009a). Organometallics, 28, 6559-6566.],b[Luzyanin, K. V., Tskhovrebov, A. G., Guedes da Silva, M. F. C., Haukka, M., Pombeiro, A. J. L. & Kukushkin, V. Y. (2009b). Chem. Eur. J. 15, 5969-5978.]); Tskhovrebov et al. (2011[Tskhovrebov, A. G., Luzyanin, K. V., Dolgushin, F. M., Guedes da Silva, M. F. C., Pombeiro, A. J. L. & Kukushkin, V. Y. (2011). Organometallics, 30, 3362-3370.]); Chay et al. (2012[Chay, R. S., Luzyanin, K. V., Kukushkin, V. Y., Guedes da Silva, M. F. C. & Pombeiro, A. J. L. (2012). Organometallics, 31, 2379-2387.]). For related structures, see: Davies et al. (1996[Davies, J. A., Hockensmith, C. M., Kukushkin, V. Y. & Kukushkin, Y. N. (1996). In Synthetic Coordination Chemistry: Principles and Practice. Singapore: World Scientific.]); Bertani et al. (1991[Bertani, R., Mozzon, M., Michelin, R. A., Benetollo, F., Bombieri, G., Castilho, T. J. & Pombeiro, A. J. L. (1991). Inorg. Chim. Acta, 189, 175-187.]); Bonati & Minghetti (1970[Bonati, F. & Minghetti, G. (1970). J. Organomet. Chem. 24, 251-256.]); Luzyanin et al. (2009a[Luzyanin, K. V., Tskhovrebov, A. G., Carias, M. C., Guedes da Silva, M. F. C., Pombeiro, A. J. L. & Kukushkin, V. Y. (2009a). Organometallics, 28, 6559-6566.],b[Luzyanin, K. V., Tskhovrebov, A. G., Guedes da Silva, M. F. C., Haukka, M., Pombeiro, A. J. L. & Kukushkin, V. Y. (2009b). Chem. Eur. J. 15, 5969-5978.]); Michelin et al. (1988a[Michelin, R. A., Zanotto, L., Braga, D., Sabatino, P. & Angelici, R. J. (1988a). Inorg. Chem. 27, 85-92.],b[Michelin, R. A., Zanotto, L., Braga, D., Sabatino, P. & Angelici, R. J. (1988b). Inorg. Chem. 27, 93-99.]); Rourke (2007[Rourke, J. P. (2007). In Comprehensive Organometallic Chemistry III, 1st ed., edited by A. Canty, Vol. 8, ch. 8.07, pp. 405-444. Oxford: Elsevier.]). For bond lengths in coordination complexes, see: Orpen et al. (1989[Orpen, A. G., Brammer, L., Allen, F. H., Kennard, O., Watson, D. G. & Taylor, R. (1989). J. Chem. Soc. Dalton Trans. pp. S1-S83.]).

[Scheme 1]

Experimental

Crystal data
  • [PdCl2(C15H11NO3)2]·CHCl3

  • Mr = 803.16

  • Orthorhombic, P 21 21 21

  • a = 7.4457 (1) Å

  • b = 12.1352 (4) Å

  • c = 36.1109 (11) Å

  • V = 3262.80 (15) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 1.02 mm-1

  • T = 100 K

  • 0.35 × 0.23 × 0.10 mm

Data collection
  • Nonius KappaCCD diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.])Tmin = 0.717, Tmax = 0.903

  • 24908 measured reflections

  • 9228 independent reflections

  • 7397 reflections with I > 2[sigma](I)

  • Rint = 0.046

Refinement
  • R[F2 > 2[sigma](F2)] = 0.037

  • wR(F2) = 0.067

  • S = 1.01

  • 9228 reflections

  • 408 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.61 e Å-3

  • [Delta][rho]min = -0.79 e Å-3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 3936 Friedel pairs

  • Flack parameter: -0.011 (17)

Table 1
Selected bond lengths (Å)

Pd1-C16 1.935 (3)
Pd1-C1 1.947 (3)
Pd1-Cl2 2.2979 (7)
Pd1-Cl1 2.2994 (7)

Table 2
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C4-H4...O2i 0.95 2.53 3.193 (4) 127
C6-H6...O6ii 0.95 2.53 3.433 (4) 158
C19-H19...O5iii 0.95 2.37 3.182 (3) 143
C20-H20...Cl1iv 0.95 2.80 3.622 (3) 145
C31-H31...Cl1v 1.00 2.77 3.607 (3) 141
C31-H31...Cl2v 1.00 2.67 3.513 (3) 142
Symmetry codes: (i) [-x+1, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]; (ii) [-x+1, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]; (iii) [x+{\script{1\over 2}}, -y+{\script{3\over 2}}, -z+2]; (iv) [x-{\script{1\over 2}}, -y+{\script{3\over 2}}, -z+2]; (v) x-1, y+1, z.

Data collection: COLLECT (Nonius, 1997[Nonius (1997). COLLECT. Nonius BV, Delft, The Netherlands.]); cell refinement: DENZO and SCALEPACK (Otwinowski & Minor, 1997[Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.]); data reduction: DENZO and SCALEPACK; 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: DIAMOND (Brandenburg, 2009[Brandenburg, K. (2009). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: SHELXL97.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: ZQ2184 ).


Acknowledgements

This work was supported by the Russian Fund for Basic Research (grant 12-03-00076).

References

Banfi, L. & Riva, R. (2005). Org. React. pp. 1-140.
Bertani, R., Mozzon, M., Michelin, R. A., Benetollo, F., Bombieri, G., Castilho, T. J. & Pombeiro, A. J. L. (1991). Inorg. Chim. Acta, 189, 175-187.  [CrossRef] [ChemPort] [ISI]
Bonati, F. & Minghetti, G. (1970). J. Organomet. Chem. 24, 251-256.  [CrossRef] [ChemPort]
Boyarskiy, V. P., Luzyanin, K. V. & Kukushkin, V. Y. (2012). Coord. Chem. Rev. 256, 2029-2056.  [ISI] [CrossRef] [ChemPort]
Brandenburg, K. (2009). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Chay, R. S., Luzyanin, K. V., Kukushkin, V. Y., Guedes da Silva, M. F. C. & Pombeiro, A. J. L. (2012). Organometallics, 31, 2379-2387.  [CrossRef] [ChemPort]
Davies, J. A., Hockensmith, C. M., Kukushkin, V. Y. & Kukushkin, Y. N. (1996). In Synthetic Coordination Chemistry: Principles and Practice. Singapore: World Scientific.
Flack, H. D. (1983). Acta Cryst. A39, 876-881.  [CrossRef] [details]
Luzyanin, K. V., Tskhovrebov, A. G., Carias, M. C., Guedes da Silva, M. F. C., Pombeiro, A. J. L. & Kukushkin, V. Y. (2009a). Organometallics, 28, 6559-6566.  [CrossRef] [ChemPort]
Luzyanin, K. V., Tskhovrebov, A. G., Guedes da Silva, M. F. C., Haukka, M., Pombeiro, A. J. L. & Kukushkin, V. Y. (2009b). Chem. Eur. J. 15, 5969-5978.  [CSD] [CrossRef] [PubMed] [ChemPort]
Michelin, R. A., Zanotto, L., Braga, D., Sabatino, P. & Angelici, R. J. (1988a). Inorg. Chem. 27, 85-92.  [CrossRef] [ChemPort] [ISI]
Michelin, R. A., Zanotto, L., Braga, D., Sabatino, P. & Angelici, R. J. (1988b). Inorg. Chem. 27, 93-99.  [CrossRef] [ChemPort] [ISI]
Nonius (1997). COLLECT. Nonius BV, Delft, The Netherlands.
Orpen, A. G., Brammer, L., Allen, F. H., Kennard, O., Watson, D. G. & Taylor, R. (1989). J. Chem. Soc. Dalton Trans. pp. S1-S83.  [CrossRef]
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.
Rourke, J. P. (2007). In Comprehensive Organometallic Chemistry III, 1st ed., edited by A. Canty, Vol. 8, ch. 8.07, pp. 405-444. Oxford: Elsevier.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Slaughter, L. M. (2012). ACS Catal. 2, 1802-1816.  [CrossRef] [ChemPort]
Tskhovrebov, A. G., Luzyanin, K. V., Dolgushin, F. M., Guedes da Silva, M. F. C., Pombeiro, A. J. L. & Kukushkin, V. Y. (2011). Organometallics, 30, 3362-3370.  [CrossRef] [ChemPort]


Acta Cryst (2012). E68, m1476-m1477   [ doi:10.1107/S1600536812045801 ]

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