J. Gallagher, M. Farrell, Niall Hehir
Oct 7, 2019
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Journal
Crystal Growth & Design
Abstract
The physicochemical properties of a 3 × 3 isomer grid of mono-chlorobenzamides (Clxx) are reported with comprehensive studies of their crystal structures and interaction environments (Clx = para-/meta-/ortho-chlorobenzoyl and x = para-/meta-/ortho-aminopyridine substitutions). The nine compound Clxx series was synthesized from the three p-/m-/o-chlorobenzoyl chlorides and three p-/m-/o-aminopyridine isomers using standard synthetic procedures. Clxx exhibits some similarities to the related Fxx and Brxx congeners, e.g., the isomorphous behavior of Clpp (para-chloro-N′-(para-pyridyl)benzamide) with several close relatives, and there are five isomorphous pairs of Clxx and Brxx crystal structures. Notably, Clmp and Clpm both crystallize with Z′ = 4 in space group P1 but show important differences. The overall lack of isomers crystallizing with solvate molecules is noteworthy, except for Clmm·(H2O). In all Clxx crystal structures, strong N–H···N hydrogen bonds form; however, Clpo also crystallizes as the unex...