Crystal structures of two 2,9-di-thia-13-aza-dispiro-[4.1.4(7).3(5)]tetra-decan-6-ones

In the title compounds 4,11-dihy-droxy-13-methyl-1,8-di-p-tolyl-2,9-di-thia-13- aza-dispiro-[4.1.4(7).3(5)]tetra-decan-6-one, C26H31NO3S2, (I), and 13-benzyl-4,11-dihy-droxy-1,8-bis-(4-methyl-phen-yl)-2,9-di-thia-13-aza-dispiro-[4.1.4(7).3(5)]tetradecan-6-one, C32H35NO3S2, (II), the piperidine rings adopt distorted chair conformations. The thio-phene rings in (I) have envelope conformations, with the spiro C atoms as the flaps. In (II), one thio-phene ring (D) has an envelope conformation, with the hy-droxy-substituted C atom as the flap, while the other thio-phene ring (E) has a twisted conformation on the C-C bond involving the spiro C atom and the toluyl-substituted C atom. In (I), the mean plane of the piperidine ring makes dihedral angles of 75.16 (9) and 73.33 (8)° with the mean planes of the thio-phene rings (D and E), respectively. In (II), the corresponding dihedral angles are 70.95 (11) and 77.43 (12)°. In both compounds, there is an intra-molecular O-H⋯O hydrogen bond forming an S(6) ring motif. In the crystal of (I), mol-ecules are linked via O-H⋯N and C-H⋯O hydrogen bonds, forming chains along [010]. There are also π-π inter-actions present involving inversion-related benzene rings, linking the chains to form slabs parallel to (100). In the crystal of (II), mol-ecules are linked via O-H⋯O hydrogen bonds, forming inversion dimers with an R 4 (4)(8) ring motif. The dimers are linked by C-H⋯π inter-actions, forming slabs parallel to (001).