Cyclic Imide and Open-Chain Amide Carboxylic Acid Derivatives from the Facile Reaction of cis-Cyclohexane-1,2-Dicarboxylic Anhydride with Three Substituted Anilines

摘要

The structures of the compounds from the reaction of cis-cyclohexane-1,2-dicarboxylic anhydride with 4-chloroaniline [rac-2-[(4-chlorophenyl)carbamoyl]-cis-cyclohexane-1-carboxylic acid] (1), 4-bromoaniline [2-(4-bromophenyl)-3a,4,5,6,7,7a-hexahydroisoindole-1,3-dione] (2) and 3-carboxy-4-hydoxyaniline (5-aminosalicylic acid) [2-(3-carboxy-4-hydroxyphenyl)- 3a,4,5,6,7,7a-hexahydroisoindole-1,3-dione] (3) have been determined at 200 K. Crystals of the open-chain amide carboxylic acid 1 are orthorhombic, space group Pbcn, with unit cell dimensions a = 20.1753(10), b = 8.6267(4), c = 15.9940(9) Å, and Z = 8. Compounds 2 and 3 are cyclic imides, with 2 monoclinic having space group P21 and Z = 4, with cell dimensions a = 11.5321(3), b = 6.7095(2), c = 17.2040(5) Å, β = 102.527(3)°. Compound 3 is orthorhombic, space group P212121 with Z = 4 and cell dimensions a = 6.4642(3), b = 12.8196(5), c = 16.4197(7) Å. Molecules of 1 form hydrogen-bonded cyclic carboxylic acid dimers [graph set R 2 2 (8)] which are extended into a two-dimensional layered structure through amide-group associations: 3 forms into one-dimensional zigzag chains through carboxylic acid···imide O-atom hydrogen bonds, while compound 2 is essentially unassociated. With both cyclic imides 2 and 3, disorder is found which involves the presence of partial enantiomeric replacement of the cis-1,2-substituted cyclohexane ring systems.