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The formation of the salt and neutral molecule cocrystal from equimolar solution of heliamine and bicyclo[2.2.1]hept‐5‐ene‐ endo ‐2,3‐dicarboxylic acid
Author(s) -
Shishkina Svitlana V.,
Isaiev Ivan A.,
Urzhuntseva Viktoriya V.,
Palchykov Vitalii A.
Publication year - 2019
Publication title -
acta crystallographica section b
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.604
H-Index - 33
ISSN - 2052-5206
DOI - 10.1107/s205252061900115x
Subject(s) - chemistry , cocrystal , molecule , dicarboxylic acid , bicyclic molecule , hydrogen bond , salt (chemistry) , crystallization , crystal structure , ene reaction , carboxylic acid , stereochemistry , hydrolysis , polymer chemistry , crystallography , organic chemistry
The possible interaction of 6,7‐dimethoxy‐1,2,3,4‐tetrahydroisoquinoline (heliamine) with bicyclo[2.2.1]hept‐5‐ene‐ endo ‐2,3‐dicarboxylic acid anhydride has been studied. Instead of the reaction with heliamine, the acid anhydride was hydrolyzed into the appropriate dicarboxylic acid. An equimolar mixture of unreacted heliamine and in‐situ ‐generated dicarboxylic acid crystallized in space group P 2 1 / c . The comprehensive study of the obtained crystals shows that the peculiarities of the crystallization process lead to the formation of the salt‐cocrystal structure where the dianion interacts simultaneously with two cations forming a chain as the primary structural motif. The neutral molecules of dicarboxylic acid link the dianions of the neighbouring chains, forming a layer as the secondary structural motif. As a result, the stronger hydrogen bonds formed by the neutral molecules play a secondary role in the crystal structure formation.