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Halogen bonded cocrystals of N-bromophthalimide with2-chloro- and 2-bromopyridine

N-Haloimides are commercially available compounds, commonly used for halogenation in organic synthesis. Since they possess an extremely polarized halogen atom, they represent a new group of potent halogen bond (XB) donors that form very strong and close-to- linear halogen bonds with N- and O-containing acceptors via the robust (CO)2N– X∙∙∙N halogen bond synthon (X = Br, I) [1-3]. As a member of this group, N-bromophthalimide (nbph) has shown significant potential as a halogen bond donor for preparation of binary molecular solids with nitrogen bases [4]. In this work we present the cocrystallization of N-bromophthalimide (nbph) by both mechanochemical synthesis and the conventional solution-based method. As cocrystal coformers, we have selected 2-chloropyridine (2ClPy) and 2-bromopyridine (2BrPy). From a crystal engineering standpoint, the coformers are interesting due to the presence of a pyridine nitrogen atom as a potential strong halogen bond acceptor and an additional halogen atom (Br or Cl) as a potential acceptor and donor of another halogen bond. Obtained cocrystals were isostructural, with the dominant supramolecular interaction being the halogen bond between the N- bromophthalimide bromine and the pyridine nitrogen, while the halogen of the pyridine ring participated only in substantially longer halogen- halogen (type I) contacts.

halogen bond, cocrystals, N-bromophthalimide, halogenopiridines

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