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Synthon preference in the cocrystal of 3,4,5‐trifluorophenylboronic acid with urea
Author(s) -
Kopczyńska Karolina,
Marek Paulina H.,
Banaś Bartłomiej,
Madura Izabela D.
Publication year - 2017
Publication title -
acta crystallographica section c
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.304
H-Index - 17
ISSN - 2053-2296
DOI - 10.1107/s2053229617013675
Subject(s) - synthon , cocrystal , crystal engineering , supramolecular chemistry , hydrogen bond , chemistry , crystallography , urea , intermolecular force , crystal structure , stereochemistry , molecule , organic chemistry
The comprehensive description of the crystal structure of a novel 1:1 cocrystal of 3,4,5‐trifluorophenylboronic acid with urea, C 6 H 4 BF 3 O 2 ·CH 4 N 2 O, is presented. Both components are good candidates for crystal engineering as they can create a variety of supramolecular synthons. The preference for the formation of different hetrosynthons is verified based on theoretical calculations. The syn – anti conformation of boronic acid has been found to be the most favourable in the formation of intermolecular interactions with urea. Moreover, the distortions present in the boron coordination sphere have been described quantitatively based on experimental data according to bond‐valence vector model calculations. The results revealed that the deformation of the sphere is typical for a syn – anti conformation of boronic acids. The supramolecular structure of the cocrystal is composed of large synthons in the form of layers made up of O—H…O and N—H…O hydrogen bonds. The layers are joined via N—H…F hydrogen bonds which are unusual for urea cocrystal structures.