V. Kravtsov, M. Fonari, Мaria Gdaniec
Jun 13, 2012
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Journal
Journal of Molecular Structure
Abstract
Abstract Treatment of 7-bromo-5-(2′-chloro)phenyl-3-hydroxy-1,2-dihydro-3 H -1,4-benzodiazepin-2-one ( 1 ) with methyl or hexyl tosylate resulted in 7-bromo-5-(2′-chloro)phenyl-3-hydroxy-1-methyl-1,2-dihydro-3 H -1,4-benzodiazepin-2-one ( 2 ) and 7-bromo-5-(2′-chloro)phenyl-1-hexyl-1,2,4,5-tetrahydro-3 H -1,4-benzodiazepin-2,3-dione ( 3 ). As confirmed by X-ray crystallography, the two products differ not only in the identity of the alkyl substituent in position 1 of the benzodiazepine fragment but also crystallize in different molecular forms resulting from proton migration. This alteration of the molecular structure leads to a significant change in the conformation of the central molecular fragment and influences the assembly mode in the crystal. In 3 , centrosymmetric dimers formed via a pair of N H⋯O hydrogen bonds are further linked into chains via C Br⋯O C halogen bond interaction. In turn in 2 there are two symmetry independent molecules, each giving a different set of intermolecular interactions. One of the molecules forms a dimer via O H⋯O interactions whereas the second one generates chain via C Br⋯O C halogen bond that is also assisted by a weak O H⋯Br hydrogen bond.