Crystal structures of the sulfones of 2,3-diphenyl-2,3-di-hydro-4 H-1,3-benzo-thia-zin-4-one and 2,3-diphenyl-2,3-di-hydro-4 H-pyrido[3,2- e][1,3]thia-zin-4-one

Hemant P Yennawar; Tapas K Mal; Carlos N Pacheco; Anthony F Lagalante; Mark A Olsen; Michael W Russell; Grace C Muench; Quentin J Moyer; Lee J Silverberg

doi:10.1107/S2056989023001524

Crystal structures of the sulfones of 2,3-diphenyl-2,3-di-hydro-4 H-1,3-benzo-thia-zin-4-one and 2,3-diphenyl-2,3-di-hydro-4 H-pyrido[3,2- e][1,3]thia-zin-4-one

Acta Crystallogr E Crystallogr Commun. 2023 Feb 23;79(Pt 3):221-225. doi: 10.1107/S2056989023001524. eCollection 2023 Feb 1.

Authors

Hemant P Yennawar¹, Tapas K Mal², Carlos N Pacheco², Anthony F Lagalante³, Mark A Olsen³, Michael W Russell⁴, Grace C Muench⁴, Quentin J Moyer⁴, Lee J Silverberg⁴

Affiliations

¹ Department of Biochemistry and Molecular Biology Pennsylvania State University, University Park, PA 16802, USA.
² Department of Chemistry, The Pennsylvania State University, University Park, PA 16802, USA.
³ Mendel Science Center, Villanova University, 800 Lancaster Avenue, Villanova, PA 19085, USA.
⁴ Pennsylvania State University, Schuylkill Campus, 200 University Drive, Schuylkill Haven, PA 17972, USA.

Abstract

The title sulfones, 2,3-diphenyl-2,3-di-hydro-4H-1,3-benzo-thia-zine-1,1,4-trione, C₂₀H₁₅NO₃S, and 2,3-diphenyl-2,3-di-hydro-4H-pyrido[3,2-e][1,3]thia-zine-1,1,4-trione, C₁₉H₁₄N₂O₃S, crystallize in space group P2₁/n with two mol-ecules in each of the asymmetric units and have almost identical unit cells and extended structures. In both structures, the thia-zine rings exhibit a screw-boat pucker. The inter-molecular inter-actions observed are C-H⋯O-type hydrogen bonds and parallel partial π-π stacking between the fused aromatic rings (benzo- or pyrido-) of the core of the mol-ecules within each asymmetric unit, and also connecting to mol-ecules with translational periodicity in the a-axis direction in what can be described as columns (two per asymmetric unit) of stacked mol-ecules with alternating chirality. The pendant phenyl groups of both mol-ecules do not participate in aromatic ring inter-actions.

Keywords: 1,3-thiazin-4-one; S-oxidation; crystal structure; screw-boat pucker; sulfone.

Grants and funding

Research reported here was conducted on instrumentation funded by National Science Foundation: CHEM-0131112 for the Bruker AXS diffractometer, and SIG S10 grants of the National Institutes of Health under award numbers 1S10OD028589–01 and 1S10RR023439–01, for the Rigaku diffraction system to Dr Neela Yennawar.