Meso-(1S*,21R*)-25-methyl-8,11,14-trioxa- 22,24,25-triazatetracyclo-[19.3.1.02,7.015,20]pentacosa-2, 4,6,15(20),16,18-hexaene-23-thione chloroform monosolvate

Abstract

The title compound crystallizes as a chloroform solvate, C 20H23N3O3S·CHCl3, with two crystallographically independent units. The independent units have distinctly different interaction patterns between the azacrown macrocycle and the chloroform solvent molecule. In one of them, the chloroform molecule forms C - H···N and Cl···H - C hydrogen bonds with the azacrown macrocycle (as a proton donor and an acceptor, respectively), whereas in the other, one of the chloroform molecules is bound to the azacrown macrocycle by an attractive Cl···O [3.080 (3)Å] interaction. The azacrown macrocycles of different units are structurally similar; the aza-14-crown-3-ether ring adopts a bowl conformation with dihedral angles between the planes of the fused benzene rings of 60.7 (1) and 68.0 (1)°. The triazinanethione ring in both cases has a sofa conformation. The crystal packing is characterized by N - H···S, N - H···O, C - H···Cl and C - H···S hydrogen bonds.