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Two crystal structures of chalcones, or 1,3‐diarylprop‐2‐en‐1‐ones, are presented; both contain a p‐methyl substitution on the 3‐Ring, but differ with respect to the m‐substitution on the 1‐Ring. Their systematic names are (2E)‐3‐(4‐methylphenyl)‐1‐(3‐{[(4‐methylphenyl)methylidene]amino}phenyl)prop‐2‐en‐1‐one (C24H21NO) and N‐{3‐[(2E)‐3‐(4‐methylphenyl)prop‐2‐enoyl]phenyl}acetamide (C18H17NO2), which are abbreviated as 3′‐(N=CHC6H4‐p‐CH3)‐4‐methylchalcone and 3′‐(NHCOCH3)‐4‐methylchalcone, respectively. Both chalcones represent the first reported acetamide‐substituted and imino‐substituted chalcone crystal structures, adding to the robust library of chalcone structures within the Cambridge Structural Database. The crystal structure of 3′‐(N=CHC6H4‐p‐CH3)‐4‐methylchalcone exhibits close contacts between the enone O atom and the substituent arene ring, in addition to C…C interactions between the substituent arene rings. The structure of 3′‐(NHCOCH3)‐4‐methylchalcone exhibits a unique interaction between the enone O atom and the 1‐Ring substituent, contributing to its antiparallel crystal packing. In addition, both structures exhibit π‐stacking, which occurs between the 1‐Ring and R‐Ring for 3′‐(N=CHC6H4‐p‐CH3)‐4‐methylchalcone, and between the 1‐Ring and 3‐Ring for 3′‐(NHCOCH3)‐4‐methylchalcone.
Acta Crystallographica Section C Crystal Structure Communications – Wiley
Published: Jun 1, 2023
Keywords: chalcone; phenylmethanimine; acetamide; π‐stacking; edge‐to‐face; crystal structure; Hirshfeld analysis; energy framework; BSA binding
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