Six 1-aroyl-4-(4-methoxyphenyl)piperazines: similar molecular structures but different patterns of supramolecular assembly

Haruvegowda Kiran Kumar, Hemmige S. Yathirajan, Belakavadi K. Sagar, Sabine Foro, Christopher Glidewell

Research output: Contribution to journalArticlepeer-review

4 Citations (Scopus)

Abstract

Six new 1-aroyl-4-(4-meth­oxy­phen­yl)piperazines have been prepared, using coupling reactions between benzoic acids and N-(4-meth­oxy­phen­yl)piperazine. There are no significant hydrogen bonds in the structure of 1-benzoyl-4-(4-meth­oxy­phen­yl)piperazine, C18H20N2O2, (I). The mol­ecules of 1-(2-fluoro­benzo­yl)-4-(4-meth­oxy­phen­yl)piperazine, C18H19FN2O2, (II), are linked by two C—H⋯O hydrogen bonds to form chains of rings, which are linked into sheets by an aromatic π–π stacking inter­action. 1-(2-Chloro­benzo­yl)-4-(4-meth­oxy­phen­yl)piperazine, C18H19ClN2O2, (III), 1-(2-bromo­benzo­yl)-4-(4-meth­oxy­phen­yl)piperazine, C18H19BrN2O2, (IV), and 1-(2-iodo­benzo­yl)-4-(4-meth­oxyphen­yl)piperazine, C18H19IN2O2, (V), are isomorphous, but in (III) the aroyl ring is disordered over two sets of atomic sites having occupancies of 0.942 (2) and 0.058 (2). In each of (III)–(V), a combination of two C—H⋯π(arene) hydrogen bonds links the mol­ecules into sheets. A single O—H⋯O hydrogen bond links the mol­ecules of 1-(2-hy­droxy­benzo­yl)-4-(4-meth­oxy­phen­yl)piperazine, C18H20N2O3, (VI), into simple chains. Comparisons are made with the structures of some related compounds.
Original languageEnglish
Pages (from-to)1253-1260
Number of pages8
JournalActa Crystallographica Section E
Volume75
Issue number8
Early online date26 Jul 2019
DOIs
Publication statusPublished - Aug 2019

Keywords

  • Piperazines
  • Crystal structure
  • Isomorphism problem
  • Disorder
  • Hydrogen bonding
  • Supramolecular assembly

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