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Balance of forces between various contacts in crystal structures of two isomeric benzo‐condensed dibromodihydroxy‐containing compounds
Author(s) -
Brehmer Thomas H.,
Weber E.,
Cano Felíx H.
Publication year - 2000
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(200001)13:1<63::aid-poc194>3.0.co;2-e
Subject(s) - chemistry , crystal structure , supramolecular chemistry , crystallization , crystallography , solvent , toluene , crystal (programming language) , molecule , hydrogen bond , lattice energy , chloroform , context (archaeology) , polymorphism (computer science) , stereochemistry , organic chemistry , paleontology , biochemistry , computer science , genotype , gene , biology , programming language
Various forces influence the formation of a crystal structure and sometimes an unstable balance between different supramolecular interactions is the reason for polymorphism. Four crystal structures relating to the interplay between bromine contacts, aromatic interactions, hydrogen bonding and the influence of the solvent used in the crystallization process are reported. In this context 1 and 2 were synthesized as model compounds both containing two hydroxy groups and two bromophenyl substituents in a cis configuration attached at different sides to the basic 9,10‐dihydroanthracene subunit. Variation in the position of the bromo substituents in 1 and 2 allows further comparison with reference to interaction modes and crystal packing. A variety of interactions (O—H…O, O—H…Br, Br…Br) are realized in two crystal modifications of 1, 1A and 1B , with similar molecular geometry but considerably different packing relationships. The balance of forces between the possible contacts and their endeavour to control the crystal packing is influenced by the solvent which is used for crystallization. Modification 1A crystallized from pure toluene, whereas for 1B toluene with a trace of chloroform was used. In pure chloroform 1 includes solvent molecules in a host lattice, forming a clathrate structure 1C [ 1 ·CHCl 3 (1:1)] with packing motifs similar to the structure 1B . Copyright © 2000 John Wiley & Sons, Ltd.