The old concept of complementarity, connected with a process of molecular recognition represents a simple approach to understand molecular assembling. The noncovalent interactions governing (self)-assemblies are fundamental for supramolecular chemistry and crystal engineering. Among noncovalent interactions governing molecular assembling hydrogen bonding plays a leading role. A few examples of molecular assembling relevant for life processes and (bio)nano materials reveal an importance of this phenomenon. Systematic analysis of hydrogen bonding patterns as a function of proton donor and acceptor properties, and the stereochemical parameters, including chirality is presented for a large number of bis(amino acid) and bis(amino alcohol) diamides with oxalyl, phthaloyl, and fumaroyl bridges. Particular attention will be given to a molecular topology of such hydrogen bonded assemblies in view of crystal engineering.