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distances were constrained to values determined by neutron scattering
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strained to Uiso(H) = 1.5 Ueq(C) for hydrogen atoms bonded to sp3 and
Uiso(H) = 1.2 Ueq(C) for those bonded to sp2 carbon atoms. For struc-
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freely. In both refinements 10 resolution dependent scale factors were
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[8] N. A. Pott, Picolylphosphan-Januskopfliganden an Gruppe 14
Metallen, Master of Education Thesis, Universität Göttingen,
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The multipole refinement was carried out on F2 with the full-matrix-
least-squares refinement program XDLSM implemented in the
XD2006 program package.[19] For 1 the resolution was truncated at
sin(θ)/λ = 1.1 Å–1 and for 2 at sin(θ)/λ = 1.0416 Å–1. For both refine-
ments a sigma cut off of 0 was used. The weighting schemes
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were w2 = 1/[σ2(Fo ) + (0.01·P)2 + 0.05 P] (1) and w2 = 1/[σ2(Fo ) +
2
2
2
2
(0.03·P)2 + 0.09 P] (2) with P = 0.3333·Fo + 0.6667·Fc . In both
refinements highest chemical and local non-crystallographic symmetry
was assumed in the beginning. For 2 the chemical and local symmetry
was lowered during the refinement. In the final cycles all parameters
except κ’ (1) and κ (2) were refined together until convergence was
reached. Detailed crystallographic information is summarized in
Table 1. Information about multipole populations, Hirshfeld test re-
sults, residual density analysis plots and detailed information on bond-
critical points are presented in the Supporting Information.
[11] T. Stey, J. Henn, D. Stalke, Chem. Commun. 2007, 413–415.
[12] A. Kermagoret, F. Tomicki, P. Braunstein, Dalton Trans. 2008,
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[13] T. Tatic, H. Ott, D. Stalke, Eur. J. Inorg. Chem. 2008, 3765–3768.
[14] a) L. Lochmann, J. Pospísil, D. Lím, Tetrahedron Lett. 1966, 2,
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[15] I. Objartel, Design of Phosphorus Centered Janus-Head Ligands,
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[16] Cambridge Structural Database, release 5.32, 2010.
[17] T. Schulz, K. Meindl, D. Leusser, D. Stern, J. Graf, C.
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[18] G. M. Sheldrick, Acta Crystallogr., Sect. A 2008, 64, 112–122.
[19] A. Volkov, P. Macchi, L. J. Farrugia, C. Gatti, P. R. Mallinson, T.
Richter, T. Koritsanszky, XD2006, A Computer Program Package
for Multipole Refinement, Topological Analysis of Charge Densi-
ties and Evaluation of Intermolecular Energies from Experimental
or Theoretical Structure Factors, 2006.
CCDC-922678, and -922679 contain the supplementary crystallo-
graphic data for 1 and 2. These data can be obtained free of charge
Supporting Information (see footnote on the first page of this article):
Crystallographic tables and CheckCIFs of 5 and 6 in the form of tables
and CIF files and Crystallographic details for the electron density stud-
ies of 1 and 2.
Acknowledgments
[20] R. F. W. Bader, in Atoms in Molecules, Oxford University Press,
New York, 1990.
We kindly acknowledge funding from the DFG Priority Programme
1178 Experimental charge density as the key to understand chemical
interactions and the Danish National Research Foundation (DNRF93)
funded Center for Materials Crystallography (CMC) for partial sup-
port.
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Received: February 15, 2013
Published Online: May 24, 2013
2012
© 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Z. Anorg. Allg. Chem. 2013, 2005–2012