Crystal structures of two 2,3-diaryl-2,3-di-hydro-4 H -1,3-benzo-thia-zin-4-ones

• Published in: Acta crystallographica. Section E, Crystallographic communications Crystallographic communications, 2018-03, Vol.74 (Pt 3), p.363
• Main Authors: Yennawar, Hemant P, Buchwalter, Michaela J, Colburn, Baylee K, Silverberg, Lee J
• Format: Article
• Language: English
• ISSN: 2056-9890; 2056-9890

The syntheses and crystal structures of 2,3-bis-[3-(tri-fluoro-meth-yl)phen-yl]-2,3-di-hydro-4 -1,3-benzo-thia-zin-4-one (di- -CF ; C H F NOS) ( ) and 2,3-bis-(4-methyl-phen-yl)-2,3-di-hydro-4 -1,3-benzo-thia-zin-4-one (di- -CH ; C H NOS) ( ) are reported. Each structure is racemic: the asymmetric unit of consists of two mol-ecules. In both and , the six-membered 1,3-thia-zine ring is close to an envelope conformation with the chiral C atom forming the flap. In , the 2-aryl group is pseudo-equatorial, while in it is pseudo-axial. In , the pendant aryl rings form a V shape with an inter-centroid distance of 3.938 (3) Å and an acute dihedral angle of 48.3 (2)° between them. Both CF groups are disordered over two orientations in 0.687 (19):0.313 (19) and 0.667 (16):0.33 (16) ratios. In each of the independent mol-ecules of , the aryl rings are almost orthogonal to each other [dihedral angles = 85.50 (12) and 86.07 (11)°]. In both structures, the chiral C atom and the O atoms participate in C-H⋯O-type hydrogen bonding between symmetry-related mol-ecules of or the independent enanti-omers in , forming chains along the -axis direction in and the -axis direction in . Additionally, in , π-π contacts of both face-to-face and edge-to-face type, as well as π-H⋯O and π-H⋯F inter-actions are observed. In , a racemic mixture of mol-ecules forms layers in the plane linked by weak π-π and C-H⋯π inter-actions.