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

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  1 , Tapas K Mal  2 , Carlos N Pacheco  2 , Anthony F Lagalante  3 , Mark A Olsen  3 , Michael W Russell  4 , Grace C Muench  4 , Quentin J Moyer  4 , Lee J Silverberg  4
Affiliations

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 et al. Acta Crystallogr E Crystallogr Commun. .

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.

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Figures

Figure 1
Figure 1
The asymmetric unit of 1 with displacement ellipsoids drawn at 50% probability level.
Figure 2
Figure 2
The asymmetric unit of 2 with displacement ellipsoids drawn at 50% probability level.
Figure 3
Figure 3
Overlay plot of 1 and 2 where atoms S1 and S2 of the two structures are matched. The atoms that differ in the two structures, namely C2 and C22 of 1 and N2 and N4 of 2, are labeled.
Figure 4
Figure 4
Crystal packing diagram for 1 showing inter­molecular pairs of C—H⋯O hydrogen bonds. Columns (four per unit cell) of mol­ecules with alternating chirality, due to the translational periodicity down the a direction can be envisioned.
Figure 5
Figure 5
Crystal packing diagram for 2 showing strong similarity with that of 1.
See this image and copyright information in PMC

References

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