Crystal structure of 3-benzoyl-2-[(5-bromo-2-hydroxy-3-meth-oxy-benzyl-idene)amino]-4,5,6,7-tetra-hydro-benzo[b]thio-phene

Abstract

In the cyclo-hexene ring of the title compound, C23H20BrNO3S, the -(CH2)4- atoms are positionally disordered [occupancy ratio = 0.753 (6):0.247 (6)]. The ring has a half-chair conformation for both the major and minor components. The dihedral angles between the mean plane of the thio-phene ring and those of the benzene and phenyl rings are 35.2 (4) and 57.7 (3)°, respectively. The planes of the two aryl rings are twisted with respect to each other by 86.4 (6)°. In the mol-ecule, there is an O-H⋯N hydrogen bond forming an S(6) ring motif. In the crystal, mol-ecules are linked via C-H⋯O hydrogen bonds, forming chains parallel to [100].

Keywords: 2-amino­thio­phene; 4,5,6,7-tetra­hydro­benzo[b]thio­phene; Schiff base; crystal structure; hydrogen bonding.

Figure 1

A view of the mol­ecular structure of the title compound, showing the atom labelling. Displacement ellipsoids are drawn at the 30% probability level. The intra­molecular hydrogen bond is shown as a dashed line (see Table 1 ▸ for details).

Figure 2

A view along the b axis of the crystal packing of the title compound. Dashed lines indicate weak C—H⋯O hydrogen bonds (see Table 1 ▸ for details; H atoms not involved in hydrogen bonding have been omitted for clarity).