Halogenated C,N-diarylacetamides: molecular conformations and supramolecular assembly

P.S. Nayak, J. P. Jasinski, J. A. Golen, B. Narayana, M. Kaur, H. S. Yathirajan , Christopher Glidewell

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5 Citations (Scopus)


The structures of four halogenated N,2-diaryl­acetamides are reported and compared with a range of analogues. N-(4-Chloro-3-methyl­phen­yl)-2-phenyl­acetamide, C15H14ClNO, (I), and N-(4-bromo-3-methyl­phen­yl)-2-phenyl­acetamide, C15H14BrNO, (II), are isostructural in the space group P. The mol­ecules of (I) and (II) are linked into chains of rings by a combination of N-H...O and C-H...π(arene) hydrogen bonds. The mol­ecules of N-(4-chloro-3-methyl­phen­yl)-2-(2,4-di­chloro­phen­yl)acetamide, C15H12Cl3NO, (III), and N-(4-bromo-3-methyl­phen­yl)-2-(2-chloro­phen­yl)acetamide, C15H13BrClNO, (IV), are linked into simple C(4) chains by N-H...O hydrogen bonds, but significant C-H...π(arene) inter­actions are absent. The N-aryl groups in compounds (III) and (IV) adopt a different orientation, by ca 180°, from that of the corresponding groups in compounds (I) and (II), but otherwise the conformations of (I)-(IV) are very similar. Comparisons are drawn between compounds (I) and (IV) and a range of analogues of the type R1CH2CONHR2, where R2 represents a halogenated aryl ring and R1 represents either another halogenated aryl ring or a naphthalen-1-yl unit.

Original languageEnglish
Pages (from-to)889-894
Number of pages6
JournalActa Crystallographica Section C Structural Chemistry
Early online date23 Aug 2014
Publication statusPublished - 15 Sept 2014


  • Crystal structure
  • Acetamides
  • C,N-di­aryl­acetamides
  • Mol­ecular conformation
  • Supra­molecular assembly
  • Hydrogen bonding
  • Benzyl penicillins


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