TY - JOUR
T1 - Crystal structures of two solvated 2-aryl-3-phenyl-2,3-dihydro-4H-pyrido[3,2-e][1,3]thiazin-4-ones
AU - Yennawar, Hemant P.
AU - Thompson, Eric N.
AU - Li, Jennie
AU - Silverberg, Lee J.
N1 - Publisher Copyright:
© 2019 International Union of Crystallography. All rights reserved.
PY - 2019/11/1
Y1 - 2019/11/1
N2 - The synthesis and crystal structures of 2-(4-fluorophenyl)-3-phenyl-2,3-dihydro-4H-pyrido[3,2-e][1,3]thiazin-4-one toluene hemisolvate (1), C19H13FN2OS·0.5C7H8, and 2-(4-nitrophenyl)-3-phenyl-2,3-dihydro-4H-pyrido[3,2-e][1,3]thiazin-4-one isopropanol 0.25-solvate 0.0625-hydrate (2), C19H13N3O3S·0.25C3H7O·0.0625H2O, are reported. Both are racemic mixtures (centrosymmetric crystal structures) of the individual compounds and incorporate solvent molecules in their structures. Compound 2 has four thiazine molecules in the asymmetric unit. All the thiazine rings in this study show an envelope pucker, with the C atom bearing the substituted phenyl ring displaced from the other atoms. The phenyl and aryl rings in each of the molecules are roughly orthogonal to each other, with dihedral angles of about 75°. The extended structures of 1 and 2 are consolidated by C-H..O and C-H..N(π), as well as T-type (C-H..π) interactions. Parallel aromatic ring interactions (π-π stacking) are observed only in 2.
AB - The synthesis and crystal structures of 2-(4-fluorophenyl)-3-phenyl-2,3-dihydro-4H-pyrido[3,2-e][1,3]thiazin-4-one toluene hemisolvate (1), C19H13FN2OS·0.5C7H8, and 2-(4-nitrophenyl)-3-phenyl-2,3-dihydro-4H-pyrido[3,2-e][1,3]thiazin-4-one isopropanol 0.25-solvate 0.0625-hydrate (2), C19H13N3O3S·0.25C3H7O·0.0625H2O, are reported. Both are racemic mixtures (centrosymmetric crystal structures) of the individual compounds and incorporate solvent molecules in their structures. Compound 2 has four thiazine molecules in the asymmetric unit. All the thiazine rings in this study show an envelope pucker, with the C atom bearing the substituted phenyl ring displaced from the other atoms. The phenyl and aryl rings in each of the molecules are roughly orthogonal to each other, with dihedral angles of about 75°. The extended structures of 1 and 2 are consolidated by C-H..O and C-H..N(π), as well as T-type (C-H..π) interactions. Parallel aromatic ring interactions (π-π stacking) are observed only in 2.
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U2 - 10.1107/S2056989019013781
DO - 10.1107/S2056989019013781
M3 - Article
C2 - 31709091
AN - SCOPUS:85074764186
SN - 2056-9890
VL - 75
SP - 1689
EP - 1693
JO - Acta Crystallographica Section E: Crystallographic Communications
JF - Acta Crystallographica Section E: Crystallographic Communications
ER -