Co-crystallisation through halogen bonding with racemic or enantiopure sulfinamides

The structures of the racemic and enantiopure forms of a primary sulfinamide reveal a key structure-defining N-H⋯OS hydrogen bond motif that resembles the ubiquitous N-H⋯OC hydrogen bond motif of central importance in protein structures. The presence of the inherently chiral sulfinamide functional group, in contrast to the planar amide, in the hydrogen bonded chains is notable. Halogen bonding with a chiral oxygen acceptor was demonstrated in the co-crystals of the sulfinamide with 1,4- diiodotetraflurobenzene, which reveal a variety of moderate and weak hydrogen and halogen bonding acting co-operatively to form the overall architecture.