MODULAR DESIGN OF HOSTS INVOLVING A RIGID SUCCINIMIDE FRAMEWORK AND N-BONDED LATERAL GROUPS - CRYSTALLINE INCLUSION PROPERTIES AND CRYSTAL-STRUCTURES OF INCLUSION-COMPOUNDS WITH DIOXANE, MEOH, AND DMF
Weber, E; Weber, E; Finge, S; Finge, S; Csoregh, I; Csoregh, I
A series of crystalline host molecules comprising a characteristic 9,10-ethanoanthracene-11,12-dicarboxamide framework have been synthesized and studied with regard to their inclusion behavior. They follow a new design concept which is to convert a given molecule, presently of amine, aminophenol, amino alcohol, or amino acid type, by addition of a so-called "clathratogenic group" (inclusion promoting group) into a crystalline host. These hosts form crystalline inclusion compounds with a variety of uncharged organic molecules ranging from protic dipolar to rather apolar compounds (103 different inclusion species). Inclusion formation and binding modes depend on the structural features of the hosts, i.e., the type of functional groups, their number, and geometric factors. X-ray crystal structures of three inclusion species are reported: 1.dioxane (1:1) [P2(1)/n, a = 11.9757 (4) angstrom, b = 9.8442 (3) angstrom, c = 16.2371 (5) angstrom, beta = 109.196 (4)-degrees, Z = 4], 23.MeOH (1:1) [Pbca, a = 8.532 (1) angstrom, b = 18.865 (1) angstrom, c = 24.074 (2) angstrom, Z = 8], 24.DMF (1:1) [P2(1)/a, a = 15.217 (1) angstrom, b = 11.445 (1) angstrom, c = 26.685 (2) angstrom, beta = 106.15 (1)-degrees, Z = 8]. They show the compounds to be typical coordinatoclathrates with hydrogen bond interactions between host and guest. In the crystals of 1.dioxane (1:1), hydrophobically aggregated host molecules form rectangular cages, each with space enough for two H bonded guests. In 23.MeOH (1:1), the guest acts both as donor and acceptor in H bonds, resulting in endless H bonded chains of alternating host and guest molecules. The finite 1:1 host-guest associates in 24.DMF (1:1) are held together by characteristic O-H...O(C) and possibly als by (C)H...O-type interactions.<