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Crystal structures, Hirshfeld analysis, and energy framework analysis of two differently 3′‐substituted 4‐methylchalcones: 3′‐(N=CHC6H4‐p‐CH3)‐4‐methylchalcone and 3′‐(NHCOCH3)‐4‐methylchalcone

Crystal structures, Hirshfeld analysis, and energy framework analysis of two differently... 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. http://www.deepdyve.com/assets/images/DeepDyve-Logo-lg.png Acta Crystallographica Section C Crystal Structure Communications Wiley

Crystal structures, Hirshfeld analysis, and energy framework analysis of two differently 3′‐substituted 4‐methylchalcones: 3′‐(N=CHC6H4‐p‐CH3)‐4‐methylchalcone and 3′‐(NHCOCH3)‐4‐methylchalcone

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Publisher
Wiley
Copyright
Copyright © 2023 Wiley Subscription Services, Inc., A Wiley Company
ISSN
0108-2701
eISSN
2053-2296
DOI
10.1107/s2053229623003704
Publisher site
See Article on Publisher Site

Abstract

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.

Journal

Acta Crystallographica Section C Crystal Structure CommunicationsWiley

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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