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

Abstract

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).

Keywords: 2,9-di­thia-13-aza­dispiro­[4.1.47.35]]tetra­decan-6-one; crystal structure; di­spiro: hydrogen bonding; piperidine; thio­phene.

Figure 1

The mol­ecular structure of compound (I), showing the atom labelling. Displacement ellipsoids are drawn at the 30% probability level.

Figure 2

The mol­ecular structure of compound (II), showing the atom labelling. Displacement ellipsoids are drawn at the 30% probability level.

Figure 3

A view of the structural overlay of compounds (I) and (II) [compound (I) is blue and compound (II) is red].

Figure 4

The crystal packing of the compound (I), illustrating the formation of chains along [010]. Hydrogen bonds are shown as dashed lines (see Table 1 ▸). H atoms not involved in hydrogen bonding have been omitted for clarity.

Figure 5

A partial view of the crystal packing of compound (I), showing the π–π inter­action (dashed line), involving inversion-related toluyl rings. H atoms not involved in this inter­action have been omitted for clarity and the centroids are shown as small red balls.

Figure 6

The crystal packing of compound (II), viewed along the b axis. Hydrogen bonds are shown as dashed lines (see Table 2 ▸ for details). H atoms not involved in hydrogen bonding have been omitted for clarity.

Figure 7

A partial view of the crystal packing of compound (II), showing the C—H⋯π inter­actions as dashed lines (see Table 2 ▸ for details). H atoms not involved in these inter­actions have been omitted for clarity and the centroids are shown as small red balls.