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Isostructural cocrystals of N-bromophthalimide with 2-chloro- and 2-bromopyridine

N-haloimides 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–Br···N halogen bond synthon (X = Br, I) [1-3]. 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 conformers are interesting due to the presence of a pyridine nitrogen atom as a potential strong 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. [1] K. Raatikainen, K. Rissanen, CrystEngComm. 13 (2011) 6972. [2] V. Stilinović, G. Horvat, T. Hrenar, V. Nemec, D. Cinčić, Chem. Eur. J. 23 (2017) 5244. [3] J. Mavračić, D. Cinčić, B. Kaitner, CrystEngComm. 18 (2016) 3343.

N-bromophthalimide, cocrystals, halogen bonding, isostructurality

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