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

Kiran Kumar, H. and Yathirajan, H. S. and Sagar, B. K. and Foro, Sabine and Glidewell, Christopher (2019) Six 1-aroyl-4-(4-meth­­oxy­phen­yl)piperazines: similar mol­ecular structures but different patterns of supra­molecular assembly. Acta Crystallographica Section E, 75 (8). pp. 1253-1260. ISSN 2056-9890

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Official URL: https://doi.org/10.1107/S2056989019010491

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.

Item Type: Article
Uncontrolled Keywords: piperazines, crystal structure, isomorphism, disorder, hydrogen bonding, supramolecular assembly
Subjects: C Chemical Science > Chemistry
Divisions: Department of > Chemistry
Depositing User: MUL SWAPNA user
Date Deposited: 12 Oct 2019 10:53
Last Modified: 12 Oct 2019 10:53
URI: http://eprints.uni-mysore.ac.in/id/eprint/8955

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