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

Authors
Type
Published Article
Journal
Acta crystallographica. Section C, Structural chemistry
Publication Date
Volume
70
Issue
Pt 9
Pages
889–894
Identifiers
DOI: 10.1107/S2053229614018713
PMID: 25186363
Source
Medline
Keywords
  • C,N-Diarylacetamides
  • Acetamides
  • Benzyl Penicillins
  • Crystal Structure
  • Hydrogen Bonding
  • Molecular Conformation
  • Supramolecular Assembly

Abstract

The structures of four halogenated N,2-diarylacetamides are reported and compared with a range of analogues. N-(4-Chloro-3-methylphenyl)-2-phenylacetamide, C(15)H(14)ClNO, (I), and N-(4-bromo-3-methylphenyl)-2-phenylacetamide, C(15)H(14)BrNO, (II), are isostructural in the space group P-1. 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, C(15)H(12)Cl(3)NO, (III), and N-(4-bromo-3-methylphenyl)-2-(2-chlorophenyl)acetamide, C(15)H(13)BrClNO, (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 R(1)CH(2)CONHR(2), where R(2) represents a halogenated aryl ring and R(1) represents either another halogenated aryl ring or a naphthalen-1-yl unit.

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