A Model for a Lipid Membrane Stabilized by C−H···X Bonds: The Crystal Structure of the Paraffinic Ylide Trimethylammonio n-Hexadecylsulfonamidate CH3(CH2)15SO2N(−)N(+)Me3

The crystal structure of trimethylammonio n-hexadecylsulfonamidate contains antiparallel monolayers stabilized by strong C−H···O bonds (C···O 3.22 A). There are also significant C−H···X (X = N, O) bonds linking adjacent layers. The structure suggests that nitrogen ylides have potential as amphoteric surfactants. The crystallography of paraffinic monolayers is discussed and the crystal structures of n-C16H33X compounds are shown to belong to three distinct types.