Abstract
In the title compound, C14H19BrN2O2S, the 1,2,4-thia-diazinane ring adopts an envelope conformation with the N atom (attached to the sulfonyl group) as the flap, while the cyclo-hexane ring adopts a chair conformation. The mean plane of the cyclo-hexane ring is almost normal to the benzene ring and the mean plane of the 1,2,4-thia-diazinane 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-thia-diazinane ring is 4.91 (18)°. The mol-ecular structure is stabilized by an intra-molecular C-H⋯O hydrogen bond, which encloses an S(6) ring motif. In the crystal, mol-ecules are linked by N-H⋯O hydrogen bonds into chains along [10-1], forming a C(6) graph-set motif. These chains are inter-connected via C-H⋯π inter-actions, leading to chains along [-101], so finally forming sheets parallel to (010).
Highlights
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
The molecular structure is stabilized by an intramolecular C—H O hydrogen bond, which encloses an
Molecules are linked by N—H O hydrogen bonds into chains along [101], forming a C(6) graph-set motif
Summary
The sulfonamide class of drugs have been widely reported for their antibacterial and antifungal activities (Trujillo et al., 2009). 1,2,4-Benzothiadiazine 1,1-dioxides are used as antihypertensive, diuretic, antidiabetic, glutaminergic neuro modulators (Cordi et al, 1996) and K-channel inhibitors A number of benzothiadiazine 1,1dioxide derivatives have recently been reported to display numerous biological activities (Tullio et al, 2011). In view of their broad spectrum of biological activities, and in a continuation of our work on this class of compound, we have synthesized the title compound, (1), and report on its spectroscopic analysis and crystal structure. The molecular structure is stabilized by an intramolecular C—H O hydrogen bond, which forms an. A view of the molecular structure of the title molecule, showing the atom labelling. The C—H O hydrogen bond is shown as a dashed line (see Table 1 for details)
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