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. 2024 Jun 4;80(Pt 7):699-703.
doi: 10.1107/S2056989024005103. eCollection 2024 Jun 1.

Synthesis and crystal structures of two racemic 2-heteroaryl-3-phenyl-2,3-di-hydro-4 H-pyrido[3,2- e][1,3]thia-zin-4-ones

Hemant P Yennawar  1 , Tapas K Mal  2 , Mark A Olsen  3 , Anthony F Lagalante  3 , Evelyn M Louca  4 , Aloura D Gavalis  4 , Lee J Silverberg  4
Affiliations

Synthesis and crystal structures of two racemic 2-heteroaryl-3-phenyl-2,3-di-hydro-4 H-pyrido[3,2- e][1,3]thia-zin-4-ones

Hemant P Yennawar et al. Acta Crystallogr E Crystallogr Commun. .

Abstract

3-Phenyl-2-(thio-phen-3-yl)-2,3-di-hydro-4H-pyrido[3,2-e][1,3]thia-zin-4-one (C17H12N2OS2, 1) and 2-(1H-indol-3-yl)-3-phenyl-2,3-di-hydro-4H-pyrido[3,2-e][1,3]thia-zin-4-one 0.438-hydrate (C21H15N3OS·0.438H2O, 2) crystallize in space groups P21/n and C2/c, respectively. The asymmetric unit in each case is comprised of two parent mol-ecules, albeit of mixed chirality in the case of 1 and of similar chirality in 2 with the enanti-omers occupying the neighboring asymmetric units. Structure 2 also has water mol-ecules (partial occupancies) that form continuous channels along the b -axis direction. The thia-zine rings in both structures exhibit an envelope conformation. Inter-molecular inter-actions in 1 are defined only by C-H⋯O and C-H⋯N hydrogen bonds between crystallographically independent mol-ecules. In 2, hydrogen bonds of the type N-H⋯O between independent mol-ecules and C-H⋯N(π) type, and π-π stacking inter-actions between the pyridine rings of symmetry-related mol-ecules are observed.

Keywords: C—H⋯N weak hydrogen bonds; crystal structure; envolope pucker; heteroar­yl; indole; pyridine; thia­zine; thio­phene; water channel.

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Figures

Figure 1
Figure 1
The mol­ecular structure of 1 with displacement ellipsoids drawn at the 50% probability level. Mol­ecules of both chirality are seen. The thio­phene ring of mol­ecule B exhibits a rotational disorder.
Figure 2
Figure 2
The mol­ecular structure of 2 with displacement ellipsoids drawn at the 50% probability level. Both mol­ecules have the same chirality. The water O atoms (O3 to O6) at quarter occupancy each were refined without protons.
Figure 3
Figure 3
Packing diagram for 1 showing C—H⋯O and C—H⋯N type hydrogen bonds between mol­ecules.
Figure 4
Figure 4
Packing diagram for 2 viewing down the b-axis, showing N—H⋯O and C—H⋯N hydrogen bonds between mol­ecules. The π–π stacking inter­actions that hold adjacent parallel chains akin to the teeth of a zipper and partially occupied water mol­ecules forming continuous channels down the b-axis are also seen.
See this image and copyright information in PMC

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