4-(Tetrahydro-4H-thiopyran-1-oxide-4-ylidene)-cyclohexanone oxime in the solid-state. A two-dimensional network of enantiomorphous chains interconnected by weak hydrogen bonds

Abstract

From a saturated C 6 H 6 solution of racemic 4-(tetrahydro-4H-thiopyran-1-oxide-4-ylidene)-cyclohexanone oxime [1 (1-R/1-S)] the co-crystal (1) 4 ·C 6 H 6 is crystallized. Single crystal X-ray analysis showed that (1) 4 ·C 6 H 6 (P1 space group) in the solid-state consists of enantiomorphous, non-covalent polymer-like chains that contain, in an alternating fashion, the crystallographically independent enantiomers 1-R and 1-R or 1-S and 1-S , respectively. Within each chain the enantiomers are linked by 'head-to-tail' intermolecular oxime-sulfoxide hydrogen bonding [D (2)