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SUPRAMOLECULAR CRYSTALLINE COMPLEXES INVOLVING BULKY HYDROXY HOSTS: X‐RAY STRUCTURE ANALYSIS OF INCLUSION COMPOUNDS WITH ACETONE AND TOLUENE
Author(s) -
Helmle Olga,
Csöregh Ingeborg,
Weber Edwin,
Hens Thomas
Publication year - 1997
Publication title -
journal of physical organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.325
H-Index - 66
eISSN - 1099-1395
pISSN - 0894-3230
DOI - 10.1002/(sici)1099-1395(199702)10:2<76::aid-poc864>3.0.co;2-3
Subject(s) - chemistry , toluene , supramolecular chemistry , acetone , inclusion (mineral) , x ray , supramolecular assembly , polymer chemistry , crystallography , crystal structure , organic chemistry , physics , quantum mechanics , mineralogy
The structures of two solid inclusion compounds formed between roof‐shaped diarylmethanol‐substituted 9,10‐dihydro‐9,10‐ethanoanthracene hosts, 1 and 2, and acetone or toluene, 1 · acetone (2:1) and 2 · toluene (1:1), were investigated by single‐crystal x‐ray analysis. Both compounds crystallize in the monoclinic system, although in different space groups [ C 2/ c for 1 · acetone (2:1) and P 2 1 / n for 2 · toluene (1:1)]. The crystal data are as follows: 1 · acetone (2:1), a =19·314(1), b =8·451(1), c =28·533(1), β=103.38(1)°; 2 · toluene (1:1), a =9·715(5), b =29·51(2), c =9·858(6), β=104·98(4)°. Conclusions are drawn concerning the rigidity of the molecules, the nature and degree of internal molecular motions and the type of disorder present in the crystals. Both hosts 1 and 2 reveal weak intramolecular interactions between the OH group and the π‐face of the adjacent benzo ring of the ethanoanthracene moiety. The packing arrangement of 1 · acetone (2:1) is governed by weak C–H · · · O host–guest interactions, whereas the somewhat controversial C–H · · · F interactions seem to stabilize the host framework in the fluoro‐containing 2 · toluene (1:1) compound. © 1997 by John Wiley & Sons, Ltd.