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Volume 69 
Part 5 
Pages m261-m262  
May 2013  

Received 2 April 2013
Accepted 8 April 2013
Online 13 April 2013

Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.005 Å
R = 0.039
wR = 0.082
Data-to-parameter ratio = 26.7
Details
Open access

(S)-[alpha]-Benzylprolinium cis-[(S)-[alpha]-benzylprolinato]dichloridopalladium(II)

aDepartment of Chemistry, Virginia Tech, Blacksburg, VA 24061, USA
Correspondence e-mail: dhobart@vt.edu

The title complex salt, (C12H16NO2)[PdCl2(C12H14NO2)], is of interest with respect to organic and organometallic catalysis. The compound crystallizes as very small orange-red irregular prisms and the asymmetric unit contains three crystallographically distinct cation-anion pairs. The coordination geometry about the palladium atoms is square-planar with the chloride ligands cis to one another. The structure displays N-H...Cl and O-H...O hydrogen bonding such that the N-H...Cl hydrogen bonds align the cation-anion pairs in a linear fashion along [001], with the O-H...O hydrogen bonds connecting these linear strands along [100] and [010].

Related literature

For the use of benzylproline in organocatalysis, see: Sutar & Joshi (2013[Sutar, R. L. & Joshi, N. N. (2013). Tetrahedron Asymmetry, 24, 43-49.]); Cordova et al. (2004[Cordova, A., Sunden, H., Engqvist, M., Ibrahem, I. & Casas, J. (2004). J. Am. Chem. Soc. 126, 8914-8915.]); Rispens et al. (1995[Rispens, M. T., Zondervan, C. & Feringa, B. L. (1995). Tetrahedron Asymmetry, 6, 661-664.]). For other mono-amino acid halide complexes of palladium(II), see: Akat'eva et al. (2004[Akat'eva, M. E., Erofeeva, O. S., Dobrynina, N. A., Ivanova, N. A. & Efimenko, I. A. (2004). Russ. J. Coord. Chem. 30, 584-590.]); Asanin et al. (2004[Asanin, D. P., Rajkovic, S., Molnar-Gabor, D. & Djuran, M. I. (2004). Monatsh. Chem. 135, 1445-1453.]); Chernova et al. (1976[Chernova, N. N., Shakhova, L. P. & Kukushkin, Y. N. (1976). Zh. Neorg. Khim. 21, 3027-3030.], 1978[Chernova, N. N., Kurskii, I. G., Vashchenko, L. P. & Ivanchenko, O. N. (1978). Zh. Neorg. Khim. 23, 1314-1318.]); Djuran & Milinkovic (1999[Djuran, M. I. & Milinkovic, S. U. (1999). Polyhedron, 18, 3611-3616.], 2000[Djuran, M. I. & Milinkovic, S. U. (2000). Polyhedron, 19, 959-963.]); Faraglia et al. (1997[Faraglia, G., Fregona, D. & Sitran, S. (1997). Transition Met. Chem. 22, 492-496.]); Hao et al. (2007[Hao, Y.-Z., Li, Z.-X. & Tian, J.-L. (2007). J. Mol. Catal. A Chem. 265, 258-267.], 2009[Hao, Y.-Z., Zhang, Y.-L., Wang, L.-H. & Ju, X.-Y. (2009). Open Catal. J. 2, 66-70.]); Krylova et al. (1994[Krylova, L. F., Dikanskaya, L. D. & Fedotov, M. A. (1994). Koord. Khim. 20, 57-59.]); Spacu & Ungureanu-Vicol (1966[Spacu, P. & Ungureanu-Vicol, O. (1966). An. Univ. Bucuresti Ser. Stiint. Natur. 15, 109-118.]); Vicol & Harabor (1974[Vicol, O. & Harabor, P. (1974). An. Stiint. Univ. Al. I. Cuza Iasi Sect. 1c, 20, 117-123.]).

[Scheme 1]

Experimental

Crystal data
  • (C12H16NO2)[PdCl2(C12H14NO2)]

  • Mr = 587.80

  • Triclinic, P 1

  • a = 10.6095 (5) Å

  • b = 12.3870 (4) Å

  • c = 14.6878 (4) Å

  • [alpha] = 101.376 (3)°

  • [beta] = 93.421 (3)°

  • [gamma] = 101.996 (3)°

  • V = 1840.80 (11) Å3

  • Z = 3

  • Mo K[alpha] radiation

  • [mu] = 1.01 mm-1

  • T = 100 K

  • 0.19 × 0.12 × 0.11 mm

Data collection
  • Oxford Diffraction Gemini Ultra diffractometer

  • Absorption correction: gaussian (CrysAlis PRO; Agilent, 2013[Agilent (2013). CrysAlis PRO. Agilent Technologies UK Ltd, Yarnton, England.]) Tmin = 0.884, Tmax = 0.929

  • 40995 measured reflections

  • 23898 independent reflections

  • 21552 reflections with I > 2[sigma](I)

  • Rint = 0.033

Refinement
  • R[F2 > 2[sigma](F2)] = 0.039

  • wR(F2) = 0.082

  • S = 1.03

  • 23898 reflections

  • 895 parameters

  • 3 restraints

  • H-atom parameters constrained

  • [Delta][rho]max = 1.99 e Å-3

  • [Delta][rho]min = -0.77 e Å-3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 11561 Friedel pairs

  • Flack parameter: -0.039 (12)

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O4-H4...O2i 0.84 1.69 2.521 (3) 171
O8-H8A...O6ii 0.84 1.71 2.547 (3) 171
O12-H12A...O10iii 0.84 1.73 2.565 (3) 177
N1-H1...Cl3 0.93 2.46 3.334 (3) 156
N2-H2C...Cl6iv 0.92 2.45 3.249 (3) 145
N3-H3...Cl2 0.93 2.48 3.354 (3) 156
N4-H4A...Cl3 0.92 2.35 3.216 (3) 156
N5-H5...Cl4 0.93 2.44 3.319 (3) 159
N6-H6D...Cl1v 0.92 2.37 3.235 (3) 156
Symmetry codes: (i) x, y-1, z; (ii) x, y+1, z; (iii) x+1, y+1, z; (iv) x+1, y, z-1; (v) x, y, z+1.

Data collection: CrysAlis PRO (Agilent, 2013[Agilent (2013). CrysAlis PRO. Agilent Technologies UK Ltd, Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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: 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.]); software used to prepare material for publication: OLEX2.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SJ5316 ).


Acknowledgements

The authors would like to thank the Virginia Tech Department of Chemistry and the Virginia Tech Crystallography Laboratory for their support.

References

Agilent (2013). CrysAlis PRO. Agilent Technologies UK Ltd, Yarnton, England.
Akat'eva, M. E., Erofeeva, O. S., Dobrynina, N. A., Ivanova, N. A. & Efimenko, I. A. (2004). Russ. J. Coord. Chem. 30, 584-590.  [ChemPort]
Asanin, D. P., Rajkovic, S., Molnar-Gabor, D. & Djuran, M. I. (2004). Monatsh. Chem. 135, 1445-1453.  [ChemPort]
Chernova, N. N., Kurskii, I. G., Vashchenko, L. P. & Ivanchenko, O. N. (1978). Zh. Neorg. Khim. 23, 1314-1318.  [ChemPort]
Chernova, N. N., Shakhova, L. P. & Kukushkin, Y. N. (1976). Zh. Neorg. Khim. 21, 3027-3030.  [ChemPort]
Cordova, A., Sunden, H., Engqvist, M., Ibrahem, I. & Casas, J. (2004). J. Am. Chem. Soc. 126, 8914-8915.  [ISI] [PubMed] [ChemPort]
Djuran, M. I. & Milinkovic, S. U. (1999). Polyhedron, 18, 3611-3616.  [ISI] [CrossRef] [ChemPort]
Djuran, M. I. & Milinkovic, S. U. (2000). Polyhedron, 19, 959-963.  [ISI] [CrossRef] [ChemPort]
Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.  [ISI] [CrossRef] [ChemPort] [details]
Faraglia, G., Fregona, D. & Sitran, S. (1997). Transition Met. Chem. 22, 492-496.  [CrossRef] [ChemPort] [ISI]
Flack, H. D. (1983). Acta Cryst. A39, 876-881.  [CrossRef] [details]
Hao, Y.-Z., Li, Z.-X. & Tian, J.-L. (2007). J. Mol. Catal. A Chem. 265, 258-267.  [ISI] [CSD] [CrossRef] [ChemPort]
Hao, Y.-Z., Zhang, Y.-L., Wang, L.-H. & Ju, X.-Y. (2009). Open Catal. J. 2, 66-70.  [CrossRef] [ChemPort]
Krylova, L. F., Dikanskaya, L. D. & Fedotov, M. A. (1994). Koord. Khim. 20, 57-59.  [ChemPort]
Rispens, M. T., Zondervan, C. & Feringa, B. L. (1995). Tetrahedron Asymmetry, 6, 661-664.  [CrossRef] [ChemPort] [ISI]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Spacu, P. & Ungureanu-Vicol, O. (1966). An. Univ. Bucuresti Ser. Stiint. Natur. 15, 109-118.  [ChemPort]
Sutar, R. L. & Joshi, N. N. (2013). Tetrahedron Asymmetry, 24, 43-49.  [ISI] [CrossRef] [ChemPort]
Vicol, O. & Harabor, P. (1974). An. Stiint. Univ. Al. I. Cuza Iasi Sect. 1c, 20, 117-123.  [ChemPort]


Acta Cryst (2013). E69, m261-m262   [ doi:10.1107/S1600536813009525 ]

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