The crystal structures of the pronated ligand, 2,9-dimethyl-1,10-phenanthrolinium (DPH) cation with selected counter anions (chloride (1), triflate (2), and gold dicyanide (3)) are reported. The role of a hydrogen bond interaction in influencing the solid state - stacking found in all three compounds has been investigated. In the chloride, and triflate adducts 1 and 2, respectively, the solid state morphology was stabilized by additional Hbonding interaction. In particular, compound 1 displays extensive network of H-bonding interaction where stacked layers are interlinked through the H-bonding network. In compound 2, the H-bonding interaction is less pronounced and involves mainly the non-coordinating triflate anion and the protonated N atom of the cation connecting neighboring intra-layer molecules. In 3 a weaker interaction exists between the N atom of the Au(CN)2anion and the protonated N of the ligand, but the system lacks extensive intra-or inter-layer H-bonding interaction that connects the neighboring molecules.
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