13-Benzyl-4,11-dihydroxy-1,8-diphenyl-2,9-dithia-13-azadispiro[4.1.4.3]tetradecan-6-one

In the title compound, C30H31NO3S2, the piperidine ring adopts a distorted chair conformation. The thiophene rings have twisted conformations about the C—C bonds. Two of the phenyl rings in the structure are positionally disordered over two sets of sites. The crystal packing features intermolecular O—H⋯O hydrogen bonds and S⋯H, O⋯H, C⋯H and H⋯H contacts.

In the title compound, C 30 H 31 NO 3 S 2 , the piperidine ring adopts a distorted chair conformation. The thiophene rings have twisted conformations about the C-C bonds. The mean plane of the piperidine ring makes a near orthogonal conformation with the toluene ring. Two of the phenyl rings in the structure are positionally disordered over two sets of sites with occupancies of 0.56 (2)/ 0.44 (2) and 0.672 (16)/0.328 (16). A region of disordered electron density was corrected for using the SQUEEZE [Spek (2015). Acta Cryst. C71, 9-18] routine in PLATON. The given chemical formula and other crystal data do not take into account the unknown solvent molecule. In the crystal, O-HÁ Á ÁO hydrogen bonds are observed along with intramolecular SÁ Á ÁH, OÁ Á ÁH, CÁ Á ÁH and HÁ Á ÁH contacts.

Structure description
Many substituted piperidine derivatives possess a wide range of bioactivities (Pati & Banerjee, 2012). They find significant applications in drug development and their properties depend on the nature of the side groups and their orientations (Viswanathan et al., 2015). As part of our studies in this area, we herein report the crystal structure of the title compound.
The molecular structure of the title compound with atom numbering is shown in Fig. 1. The piperidine ring adopts a distorted chair conformation as observed in a similar related structure, 2 {13-benzyl-4,11-dihydroxy-1,8-bis(4-methylphenyl)-2, 9-dithia-13-azadispiro-[4.1.47.35]tetradecan-6-one; Viswanathan et al., 2015}. However, both the thiophene rings (rings D S2/C16/C15/C13/C17 and E: S1/C7/C10/C9/C8) have twisted conformations about the C-C bonds (C10-C9 in D and C13-C15 in E). In 2, ring D adopts an envelope conformation and ring E a twisted conformation about the C13-C17 bond, data reports indicating the influence of substitutional effects on the ring conformations. The mean plane of the piperidine ring A is nearly orthogonal [88.5 (3) ] to the toluene ring F. This angle is reported to be 75.09 (1) in 2 (Viswanathan et al., 2015). In addition, the dihedral angles between the mean planes of rings D and B and between E and C are 54.07 (14) and 40.5 (4) , respectively, differing significantly from the values reported for 2. An overlay analysis of the title compound (with major conformer only) for non-H atoms with the corresponding atoms in 2 has an r.m.s. deviation of 1.12 Å (Fig. 2). A similar analysis for a compound closely related to 2 (with a methyl rather than a benzyl substituent on the N atom of the central piperidine ring), the r.m.s. deviation is found to be 1.03 Å , indicating the conformational preservation of the five rings (A to E) in these structures. An intramolecular O-HÁ Á ÁO contact (Table 1) is observed. The phenyl rings attached to rings D and E are both positionally disordered over two sets of sites with occupancies of 0.56 (2)/0.44 (2) and 0.672 (16)/ 0.328 (16), respectively.
In the crystal, an O-HÁ Á ÁO interactions forms an R 4 4 (8) ring motif (Bernstein et al., 1995). This pattern is stacked along the c-axis direction, forming hollow square frames parallel to c (Fig. 3).

Figure 1
The molecular structure of the title compound with the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. H atoms are shown as circles of arbitrary radii. The minor conformations of the two disordered phenyl rings are not shown here for clarity. the main contributors to the crystal packing, followed by SÁ Á ÁH (8.4%) and OÁ Á ÁH (7.1%) contacts.

Refinement
Crystal data, data collection and structure refinement details are summarized in Table 2. A region of disordered electron density (48 e Å À3 ) located near a symmetry element (0.0 0.5 À 0.018) was corrected for using the SQUEEZE (Spek, 2015) routine in PLATON. Two phenyl rings in the modelled structure are found to be positionally disordered over two sets of sites with occupancies of 0.56 (2)/0.44 (2) and 0.672 (16)/ 0.328 (16). Hence, disorder treatment was applied with the rigid-bond restraints SIMU and DELU for completing the refinement.

Figure 4
The two-dimensional fingerprint plot for the title compound depicting the overall contribution by the various contacts.

Figure 5
The two-dimensional fingerprint plot for the title compound depicting the contribution percentage of OÁ Á ÁH contacts.

data-1
IUCrData (  Special details Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. Refinement. The hydroxy H atoms were refined as riding: O-H = 0.82 Å with U iso (H) = 1.5U eq (O)·. The C-bound H atoms were included in calculated positions and treated as riding, with C-H = 0.95-0.98 Å, and with 1.2U eq (C) for H atoms.
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å 2 )