title: Probing the shapes of chiral bis-(o-naphthalimidobenzoyl) systems using X-ray and circular dichroism methods.
abstract: CD (circular dichroism) and X-ray investigations have been carried out in order to identify the prevalent conformations and define the forces that determine the molecular and supramolecular organization of the alkyl-bridged bichromophoric [NAB, ortho-(1,8-naphthalimido)benzoyl] units, each consisting of the benzoyl substituted in the ortho position with the 1,8-naphthalimide group. The results reveal that NAB bichromophores incorporated into the same molecule exist in a variety of conformation/helicity combinations. The molecular structures are largely stabilized by local 1,3-CH/CO dipole-dipole interactions, while the crystal packing besides dispersive H...H interactions is mostly governed by multiple C-H...O(=C) and C-H...pi interactions. The relatively small contribution of pi...pi interactions comes from a pairwise off-face stacking between naphthalimide rings or from pairwise carbonyl...pi interactions. All these types of intermolecular interactions have been summarized quantitatively by means of a Hirshfeld surface analysis.
authors.affiliation: Faculty of Chemistry, Adam Mickiewicz University, Grunwaldzka 6, 60-780 Poznań, Poland. urszular@amu.edu.pl
authors.forename: Urszula
authors.initials: U
authors.lastname: Rychlewska
authors.forename: Agnieszka
authors.initials: A
authors.lastname: Plutecka
authors.forename: Marcin
authors.initials: M
authors.lastname: Hoffmann
authors.forename: Paweł
authors.initials: P
authors.lastname: Skowronek
authors.forename: Krystyna
authors.initials: K
authors.lastname: Gawrońska
authors.forename: Jacek
authors.initials: J
authors.lastname: Gawroński