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

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Date
08/2019
Author
Kiran Kumar, Haruvegowda
Yathirajan, Hemmige S.
Sagar, Belakavadi K.
Foro, Sabine
Glidewell, Christopher
Keywords
Piperazines
Crystal structure
Isomorphism problem
Disorder
Hydrogen bonding
Supramolecular assembly
QD Chemistry
DAS
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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.
Citation
Kiran Kumar , H , Yathirajan , H S , Sagar , B K , Foro , S & Glidewell , C 2019 , ' Six 1-aroyl-4-(4-methoxyphenyl)piperazines : similar molecular structures but different patterns of supramolecular assembly ' , Acta Crystallographica Section E , vol. 75 , no. 8 , pp. 1253-1260 . https://doi.org/10.1107/S2056989019010491
Publication
Acta Crystallographica Section E
Status
Peer reviewed
DOI
https://doi.org/10.1107/S2056989019010491
ISSN
2056-9890
Type
Journal article
Rights
Copyright © 2019 The Author(s). This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
Description
HSY thanks the University Grants Commission, New Delhi, for the award of a BSR Faculty Fellowship for three years.
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  • University of St Andrews Research
URI
http://hdl.handle.net/10023/18308

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