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A structural study on the solid, microcrystalline chromophore roseolumiflavin was carried out. Based on rational design considerations three binary co-crystals were prepared with a primary focus set on utilizing the imide functional group. Therefore, robust supramolecular synthons, including a carboxylic acid–amide dimer, halogen bonding, as well as a hydrogen-bonded three-point binding motif, were successfully incorporated into the multicomponent systems. All the co-crystals showed a blue-shifted fluorescence in the red range compared to the near-infrared-emitting solid roseolumiflavin. Solvatochromic studies finally elucidated that the degree of close packing between the flavin molecules within the crystal structures was decisive for the emission colour. These results render new possibilities to investigate flavins in the aspect of crystal engineering to tune optical properties of organic chromophores in the solid state. [ABSTRACT FROM AUTHOR]