Utilizing sulfoxide···iodine halogen bonding for cocrystallization
Eccles, Kevin S.
Morrison, Robin E.
Stokes, Stephen P.
O'Mahony, Graham E.
Hayes, John A.
Kelly, Dawn M.
O'Boyle, Noel M.
Moynihan, Humphrey A.
Maguire, Anita R.
American Chemical Society
The propensity of a range of different sulfoxides and sulfones to cocrystallize with either 1,2- or 1,4-diiodotetrafluorobenzene, via I•••O=S halogen bonding, was investigated. Cocrystallization occurred exclusively with 1,4-diiodotetrafluorobenzene in either a 1:1 or 1:2 stoichiometry of the organohalide and the sulfoxide, respectively, depending on the sulfoxide used. It was found that the stoichiometry observed was not necessarily related to whether the oxygen acts as a single halogen bond acceptor or if it is bifurcated; with I•••π interactions observed in two of the cocrystals synthesized. Only those cocrystals with a 1:2 stoichiometry exhibit C−H•••O hydrogen bonding in addition to I•••O=S halogen bonding. Examination of the Cambridge Structural Database shows that (i) the I•••O=S interaction is similar to other I•••O interactions, and (ii) the I•••π interaction is significant, with the distances in the two cocrystals among the shortest known.
Sulfoxides , Sulfones , Cocrystallization , Halogen bonding , Organohalide , Stoichiometry
Eccles, Kevin; Morrison, Robin; Stokes, Stephen; O'Mahony, Graham; Hayes, John; Kelly, Dawn; O'Boyle, Noel; Fabian, Laszlo; Moynihan, H.; Maguire, Anita; Lawrence, Simon E. (2012) 'Utilizing Sulfoxide...Iodine Halogen Bonding for Cocrystallization'. Crystal Growth and Design, 12 (6):2969-2977. http://dx.doi.org/10.1021/cg300189v
© 2012, American Chemical Society. This document is the Accepted Manuscript version of a Published Work that appeared in final form in Crystal Growth and Design, copyright © American Chemical Society after peer review and technical editing by the publisher.To access the final edited and published work see http://pubs.acs.org/doi/abs/10.1021/cg300189v