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The structural impact of hydrogen-donating moieties on the liquid crystalline behavior of hydrogen-bonded assemblies (HBAs) is comprehensively investigated. Therefore, a series of phenol derivatives such as phenol, catechol (CA), resorcinol (RE), hydroquinone (HQ), pyrogallol, hydroxyhydroquinone, and phloroglucinol (PHG) were combined with alkoxyazopyridines (Ap-N) yielding 49 new HBAs, which were studied with respect to their mesomorphic properties. The present study revealed significant differences in the liquid crystalline behavior of the structurally diverse assemblies, ranging from the absence of a mesophase to smectic or nematic phases. In contrast to previous studies a comprehensive crystallographic analysis provides insight into the structure-property relationships of the assemblies and proves a correlation between the supramolecular architecture and the macroscopic properties (=liquid crystallinity). More specifically, comparison of the single crystal data with the 2D X-ray diffraction patterns indicates that linear assemblies tend to form crystalline or smectic phases (for the HQ and RE, respectively), while a bent-shaped assembly yields nematic phases (for CA and PHG). Furthermore, our results suggest that segregation of aliphatic and aromatic segments, as observed in the solid state structures, supports the formation of stable mesophases. [ABSTRACT FROM AUTHOR]