Synthesis and detailed experimental and theoretical study on new urea and thiourea derivatives of chiral trianglamine are presented. In solution, the urea derivative of the trianglamine adopts cone conformation, whereas a respective thiourea derivative exists in solution predominantly as a partial cone conformer. In the crystalline phase, the thiourea trianglamine derivative adapts partial cone conformation. In the solid state, the two symmetry independent molecules of thiourea trianglamine create bilayers, containing molecules arranged in a zipper motif. The bilayers are separated by channels filled with disordered solvent molecules. The thiourea derivative of trianglimine appeared to be a simple, low molecular weight supergelator that formed stable chiral metallogels in N,N-dimethylformamide with Ag(I), Cu(I). and Cu(II) salts. The enantiomeric enrichment of the macrocycle is a necessary condition for effective gelling because neither racemic nor enantiomerically enriched samples (up to 50% ee) form metallogels. The metallogels formed from silver cations and thiourea trianglamine show reversible thixotropic property rarely observed in metallogels.