Acta Crystallographica Section C

Crystal Structure Communications

Volume 65, Part 4 (April 2009)

organic compounds

Acta Cryst. (2009). C65, o179-o182 [ doi:10.1107/S0108270109009792 ]

Diastereomers (R_C,S_P)- and (R_C,R_P)-S-methyl P-(3-azidopropyl)-N-[(1R)-1-phenylethyl]phosphonamidothioate

L. Guo, C. M. Thompson and B. Twamley

Abstract: Diastereoisomers of the title organophosphorus compound, C₁₂H₁₉N₄OPS, denoted R_CS_P, (I), and R_CR_P, (II), were structurally characterized and compared. Asymmetric phosphorus compounds are of interest with regard to the use of these systems as possible protein probes via the stereoselective delivery of an azide group tethered to the P atom into key protein regions. The diastereomers were produced in a 1:1 mixture and isolated by chromatography. Although both isomers crystallize in the same space group with superficially similar cell constants, conformational and packing differences are pronounced. Despite the conformational differences, strong intermolecular hydrogen bonding links both isomers into chains parallel to the a axis [NO = 2.8609 (18) and 2.966 (3) Å in (I) and (II), respectively], with C-H [pi] interchain interactions of ca 3.5 Å.

Formula: C₁₂H₁₉N₄OPS


	Structure factor file (CIF format) (168.6 kbytes) [ doi:10.1107/S0108270109009792/em3024Isup2.hkl ] Contains datablock I

	Structure factor file (CIF format) (165.4 kbytes) [ doi:10.1107/S0108270109009792/em3024IIsup3.hkl ] Contains datablock II

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