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Four compounds of 2,5-dichloro-3,6-dihydroxy-1,4-benzoquinone (chloranilic acid ) H 2 CA) with organic and metal complex partners, [Hmel][CA] 0.5 ‚H 2 O (1), [Htptz][HCA]‚H 2 O (2), [Fe(terpy) 2 ][CA]‚6H 2 O (3), and [TTF][CA] 0.5 [ red H 4 CA] 0.5 ( 4) (mel ) melamine, tptz ) 2,4,6-tris(2-pyridyl)-1,3,5-triazine, terpy ) 2,2′,6′,2′′-terpyridine, TTF ) tetrathiafulvalene) are synthesized and characterized by single-crystal X-ray diffraction. For the obtained compounds, chloranilic acid shows various oxidation states and hydrogen bonding modes with multistage deprotonation processes. For compounds 1 and 3, chloranilic acid shows its complete deprotonated form (CA 2-). For compound 2, the monodeprotonated form of chloranilic acid (HCA -) is observed. Interestingly, compound 4 shows a reduced form of protonated chloranilic acid (1,4-dichloro-2,3,5,6-tetrahydroxybenzene: red H 4 CA).