Acta Crystallographica Section B

Structural Science

Volume 64, Part 2 (April 2008)

research papers

Acta Cryst. (2008). B64, 196-205 [ doi:10.1107/S0108768107061770 ]

Structure-directing weak phosphoryl XHO=P (X = C, N) hydrogen bonds in cyclic oxazaphospholidines and oxazaphosphinanes

A. van der Lee, M. Rolland, X. Marat, D. Virieux, J.-N. Volle and J.-L. Pirat

Abstract: The structures of six cyclic oxazaphospholidines and three cyclic oxazaphosphinanes have been determined and their supramolecular structures have been compared. The molecules differ with respect to the functional groups attached to the central five- or six-membered rings, but have one phosphoryl group in common. The predominant feature in the supramolecular structures is the existence of relatively weak intermolecular phosphoryl XHO=P (X = C, N) hydrogen bonds, creating in nearly all cases linear zigzag or double molecular chains. The molecular chains are in general linked to each other via very weak CH [pi] or usual hydrogen-bond interactions. A survey of the Cambridge Structural Database on similar XHO=P interactions shows a very large flexibility of the XHO angle, which is in agreement with the DFT calculation reported elsewhere. The strength of the XHO=P interaction can therefore be considered as relatively weak to moderately strong, and is expected to play at least a role in the formation of secondary substructures.

Keywords: hydrogen bonding; chirality.


	Structure factor file (CIF format) (310.9 kbytes) [ doi:10.1107/S0108768107061770/gp5020Isup2.hkl ] Contains datablock I

	Structure factor file (CIF format) (584.3 kbytes) [ doi:10.1107/S0108768107061770/gp5020IIsup3.hkl ] Contains datablock CRYSTALS_cif

	Structure factor file (CIF format) (118.0 kbytes) [ doi:10.1107/S0108768107061770/gp5020IIIsup4.hkl ] Contains datablock 1

	Structure factor file (CIF format) (148.7 kbytes) [ doi:10.1107/S0108768107061770/gp5020IVsup5.hkl ] Contains datablock 1

	Structure factor file (CIF format) (128.2 kbytes) [ doi:10.1107/S0108768107061770/gp5020Vsup6.hkl ] Contains datablock V

	Structure factor file (CIF format) (129.0 kbytes) [ doi:10.1107/S0108768107061770/gp5020VIsup7.hkl ] Contains datablock CRYSTALS_cif

	Structure factor file (CIF format) (271.4 kbytes) [ doi:10.1107/S0108768107061770/gp5020VIIsup8.hkl ] Contains datablock CRYSTALS_cif

	Structure factor file (CIF format) (316.8 kbytes) [ doi:10.1107/S0108768107061770/gp5020VIIIsup9.hkl ] Contains datablock CRYSTALS_cif

	Structure factor file (CIF format) (225.1 kbytes) [ doi:10.1107/S0108768107061770/gp5020IXsup10.hkl ] Contains datablock CRYSTALS_cif

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