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The crystal structure of the 1:2 dihydrate compound of chloranilic acid (systematic name: 2,5-di-chloro-3,6-dihy-droxy-1,4-benzo-quinone) with 2-carb-oxy-pyridine (another common name: picolinic acid; systematic name: pyridine-2-carb-oxy-lic acid), namely, 2C 6 H 5.5 NO 2  0.5+ ·C 6 HCl 2 O 4  - ·2H 2 O, (I), has been determined at 180 K, and the structure of the 1:2 dihydrate compound of chloranilic acid with 2-carb-oxy-quinoline (another common name: quinaldic acid; systematic name: quinoline-2-carb-oxy-lic acid), namely, 2C 10 H 7 NO 2 ·C 6 H 2 Cl 2 O 4 ·2H 2 O, (II), has been redetermined at 200 K. This determination presents a higher precision crystal structure than the previously published structure [Marfo-Owusu &amp; Thompson (2014 ▸). X-ray Struct. Anal. Online , 30 , 55-56]. Compound (I) was analysed as a disordered structure over two states, viz. salt and co-crystal. The salt is bis-(2-carb-oxy-pyridinium) chloranilate dihydrate, 2C 6 H 6 NO 2  + ·C 6 Cl 2 O 4  2- ·2H 2 O, and the co-crystal is bis-(pyridinium-2-carboxyl-ate) chloranilic acid dihydrate, 2C 6 H 5 NO 2 ·C 6 H 2 Cl 2 O 4 ·2H 2 O, including zwitterionic 2-carb-oxy-pyridine. In both salt and co-crystal, the water mol-ecule links the chloranilic acid and 2-carb-oxy-pyridine mol-ecules through O-H⋯O and N-H⋯O hydrogen bonds. The 2-carb-oxy-pyridine mol-ecules are connected into a head-to-head inversion dimer by a short O-H⋯O hydrogen bond, in which the H atom is disordered over two positions. Compound (II) is a 1:2 dihydrate co-crystal of chloranilic acid and zwitterionic 2-carb-oxy-quinoline. The water mol-ecule links the chloranilic acid and 2-carb-oxy-quinoline mol-ecules through O-H⋯O hydrogen bonds. The 2-carb-oxy-quinoline mol-ecules are connected into a head-to-tail inversion dimer by a pair of N-H⋯O hydrogen bonds.

Crystal structures of two 1:2 dihydrate compounds of chloranilic acid with 2-carboxypyridine and 2-carboxyquinoline