Six crystal structures of substituted 2-chloroquinoline derivatives have been analysed to evaluate the role of Cl atom as a self recognizing unit resulting in the formation of Cl⋯Cl and C-H⋯Cl interactions to generate supramolecular assembly in the solid state. The features of Type I and Type II geometries associated with Cl⋯Cl interactions have been analysed to show directional preferences leading to differences in the packing motifs in these crystal structures. C-H⋯Cl interactions are generated exclusively in structures depicting Type II Cl⋯Cl interaction have been observed in these structures. © Indian Academy of Sciences.