rac-Dichlorido(1-{(diphenyl­phosphan­yl)[2-(diphenyl­phosphan­yl)phen­yl]meth­yl}ferrocene-κ2P,P′)palladium(II) dimethyl sulfoxide disolvate

Schuecker, R.; Weissensteiner, W.; Mereiter, K.

doi:10.1107/S160053681103618X

Volume 67
Part 10
Pages m1377-m1378
October 2011

Received 24 August 2011
Accepted 5 September 2011
Online 14 September 2011

Key indicators
Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.002 Å
Disorder in solvent or counterion
R = 0.021
wR = 0.055
Data-to-parameter ratio = 23.9
Details

rac-Dichlorido(1-{(diphenylphosphanyl)[2-(diphenylphosphanyl)phenyl]methyl}ferrocene-²P,P')palladium(II) dimethyl sulfoxide disolvate

Raffael Schuecker,^a Walter Weissensteiner ^a and Kurt Mereiter ^b ^*

^aInstitute of Organic Chemistry, University of Vienna, Währingerstrasse 38, A-1090 Vienna, Austria, and ^bInstitute of Chemical Technologies and Analytics, Vienna University of Technology, Getreidemarkt 9/164SC, A-1060 Vienna, Austria
Correspondence e-mail: kurt.mereiter@tuwien.ac.at

The racemic title compound, [FePdCl₂(C₅H₅)(C₃₆H₂₉P₂)]·2(CH₃)₂SO, features a Pd-chelating 1,3-diphosphine, which is substituted at a P-bearing asymmetric C atom by a ferrocenyl group. The Pd^II atom is in a distorted quadratic coordination by two P and two Cl atoms with bond lengths of 2.2414 (3) and 2.2438 (3) Å for Pd-P, and 2.3452 (3) and 2.3565 (3) Å for Pd-Cl. The conformation of the Pd complex is controlled by an intramolecular slipped [pi] - [pi] stacking interaction between a phenyl and a cyclopentadienyl ring with corresponding CC distances starting at 3.300 (2) Å and the distance between ring centroids being 3.674 (2) Å. The crystal structure is stabilized by C-HCl and C-HO hydrogen bonds. The (CH₃)₂SO solvent molecules are arranged in layers parallel to (101) and are linked in pairs by C-HO interactions. One (CH₃)₂SO molecule is orientationally disordered [occupancy ratio 0.8766 (17):0.1234 (17)] with sulfur in two positions at both sides of its C₂O triangle.

Related literature

For general information on ferrocene-based diphosphines and their applications in asymmetric catalysis, see: Togni (1996); Blaser et al. (2007); Dai & Hou (2010). For the synthesis, coordination behavior, and use in asymmetric catalysis of ligands based on [diphenylphosphanyl-(2-diphenylphosphanylphenyl)methyl]-ferrocene, see: Schuecker et al. (2010); Lotz et al. (2010).

Experimental

Crystal data

[FePdCl₂(C₅H₅)(C₃₆H₂₉P₂)]·2C₂H₆OS
M_r = 978.03
Triclinic, $[P \overline 1]$
a = 10.9878 (8) Å
b = 11.5275 (8) Å
c = 17.1405 (12) Å
= 78.720 (2)°
= 81.796 (2)°
= 78.143 (2)°
V = 2071.8 (3) Å³
Z = 2
Mo K radiation
= 1.13 mm^-1
T = 100 K
0.59 × 0.45 × 0.36 mm

Data collection

Bruker SMART APEX CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2003) T_min = 0.58, T_max = 0.67
37987 measured reflections
11991 independent reflections
11375 reflections with I > 2(I)
R_int = 0.018

Refinement

R[F² > 2(F²)] = 0.021
wR(F²) = 0.055
S = 1.02
11991 reflections
502 parameters
H-atom parameters constrained
_max = 0.59 e Å^-3
_min = -0.60 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C6-H6O1ⁱ	1.00	2.40	3.3365 (17)	156
C15-H15Cl1ⁱⁱ	0.95	2.70	3.4262 (12)	133
C19-H19Cl1	0.95	2.66	3.2410 (12)	120
C23-H23O1ⁱ	0.95	2.47	3.3239 (16)	149
C25-H25Cl1	0.95	2.70	3.5075 (13)	143
C29-H29O1ⁱ	0.95	2.45	3.3201 (16)	152
C31-H31Cl2	0.95	2.76	3.3893 (13)	125
C42-H42AO2	0.98	2.42	3.368 (2)	163
C45-H45ACl1ⁱⁱⁱ	0.98	2.83	3.6881 (16)	147
Symmetry codes: (i) -x, -y+1, -z+1; (ii) x-1, y, z; (iii) -x+1, -y+1, -z+1.

Data collection: SMART (Bruker, 2003); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT and XPREP (Bruker, 2003); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2006); software used to prepare material for publication: PLATON (Spek, 2009) and publCIF (Westrip, 2010).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: GK2404 ).

Acknowledgements

This work was kindly supported by SOLVIAS AG.

References

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