Crystal structure of (R)-6′-bromo-3,3-dimethyl-3′,4′-dihydro-2′H-spiro[cyclohexane-1,3′-1,2,4-benzothiadiazine] 1′,1′-dioxide

Abstract

In the title compound, C14H19BrN2O2S, the 1,2,4-thiadiazinane ring adopts an envelope conformation with the N atom (attached to the sulfonyl group) as the flap, while the cyclohexane ring adopts a chair conformation. The mean plane of the cyclohexane ring is almost normal to the benzene ring and the mean plane of the 1,2,4-thiadiazinane ring, making dihedral angles of 70.4 (2) and 71.43 (19)°, respectively. Furthermore, the dihedral angle between the benzene ring and the mean plane of the 1,2,4-thiadiazinane ring is 4.91 (18)°. The molecular structure is stabilized by an intramolecular C—H...O hydrogen bond, which encloses an S(6) ring motif. In the crystal, molecules are linked by N—H...O hydrogen bonds into chains along [10-1], forming a C(6) graph-set motif. These chains are interconnected via C—H...π interactions, leading to chains along [-101], so finally forming sheets parallel to (010).

Keywords

• crystal structure
• benzothiadiazine
• hydrogen bonding
• chirality