An amide cyclophane

Abstract

The title compound, 8,18-dithia-2,6-diaza-13(1,4)-piperidina-1(1,2),4(1,3),7(1,2)-tribenzenaoctadecaphane-10,15-diyne-3,6-dione, C32H30N4O2S2, is composed of a relatively planar bis­(2-mercaptophen­yl)isophthalamide unit linked to a bridging 1,4-di(but-2-yn-1-yl)piperazine unit, forming a macrocycle. The isophthalamide ring is inclined to the outer mercaptophenyl rings by 8.18 (11) and 5.59 (10)°, while these two rings are inclined to one another by 9.10 (12)°. The piperazine ring adopts a chair conformation. There are two intra­molecular N—H⋯S hydrogen bonds generating S(5) ring motifs. In the crystal, mol­ecules are linked via C—H⋯S and C—H⋯O hydrogen bonds, forming slabs lying parallel to (001). An O atom in the isophthalamide group is disordered over two positions with an occupancy ratio of 0.41 (6):0.59 (6).

Efficient Straightforward Synthesis of Amidopiperazinophanes as Versatile Novel Supramolecular Scaffolds

“…ring motifs and the structure is further stabilized by hydrogen bonds of C-H•••S and C-H•••O.The oxygen atoms of the amide carbonyl linked to the isophthaloyl ring is disordered over two positions with an occupancy ratio of 0.41(6):0.59(6) 23. …”