Crystal structures of two isomeric 2-aryl-3-phenyl-1,3-thiazepan-4-ones

Abstract

The crystal of 6-(3-nitrophenyl)-7-phenyl-5-thia-7-azaspiro[2.6]nonan-8-one (1), C19H18N2O3S, has monoclinic (P21/n) symmetry while that of its isomer 6-(4-nitrophenyl)-7-phenyl-5-thia-7-azaspiro[2.6]nonan-8-one (2), has orthorhombic (Pca21) symmetry: compound 1 has two molecules, A and B, in the asymmetric unit while 2 has one. In all three molecules, the seven-membered thiazepan ring exhibits a chair conformation with Q2 and Q3 values (Å) of 0.521 (3), 0.735 (3) and 0.485 (3), 0.749 (3) in 1 and 0.517 (5), 0.699 (5) in 2. In each structure, the phenyl rings attached to adjacent atoms of the thiazepan ring have interplanar angles ranging between 41 and 47°. Except for the nitro groups, the three molecules have similar conformations when overlayed in pairs. Both crystal structures are consolidated by C—H...O hydrogen bonds.