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dc.contributor.authorChinthal, Chayanna Harish
dc.contributor.authorKavitha, Channappa N.
dc.contributor.authorYathirajan, Hemmige S.
dc.contributor.authorForo, Sabine
dc.contributor.authorGlidewell, Christopher
dc.date.accessioned2021-02-01T10:30:10Z
dc.date.available2021-02-01T10:30:10Z
dc.date.issued2021-01-01
dc.identifier.citationChinthal , C H , Kavitha , C N , Yathirajan , H S , Foro , S & Glidewell , C 2021 , ' Six 1-halobenzoyl-4-(2-methoxyphenyl)piperazines having Z ' values of one, two or four; disorder, pseudosymmetry, twinning and supramolecular assembly in one, two or three dimensions ' , Acta Crystallographica Section E Crystallographic Communications , vol. 77 , no. 1 , pp. 5-13 . https://doi.org/10.1107/S2056989020015649en
dc.identifier.issn2056-9890
dc.identifier.otherPURE: 272522734
dc.identifier.otherPURE UUID: 37e21889-e15c-41d5-81b7-5198a117901c
dc.identifier.otherBibtex: ISI:000605200200002
dc.identifier.otherScopus: 85099029606
dc.identifier.otherWOS: 000605200200002
dc.identifier.urihttp://hdl.handle.net/10023/21351
dc.descriptionHSY thanks the University Grants Commission, New Delhi for the award of a BSR Faculty Fellowship for three years.en
dc.description.abstractSix 1-halobenzoyl-4-(2-methoxyphenyl)piperazines have been prepared using carbodiimide-mediated coupling reactions between halobenzoic acids and N-(2-methoxyphenyl)piperazine. The molecules of 1-(4-fluorobenzoyl)-4-(2-methoxyphenyl)piperazine, C18H19FN2O2 (I), are linked into a chain of rings by a combination of C-H···O and C-H···π(arene) hydrogen bonds. 1-(4-Chloro-benzoyl)-4-(2-methoxyphenyl)piperazine, C18H19ClN2O2 (II), crystallizes in the space group Pca21 with Z' = 4 and it exhibits both pseudosymmetry and inversion twinning: a combination of six C-Six 1-halobenzoyl-4-(2-meth­oxy­phen­yl)piperazines have been prepared using carbodi­imide-mediated coupling reactions between halo­benzoic acids and N-(2-meth­oxy­phen­yl)piperazine. The mol­ecules of 1-(4-fluoro­benzo­yl)-4-(2-meth­oxy­phen­yl)piperazine, C18H19FN2O2 (I), are linked into a chain of rings by a combination of C—H⋯O and C—H⋯π(arene) hydrogen bonds. 1-(4-Chloro­benzo­yl)-4-(2-meth­oxy­phen­yl)piperazine, C18H19ClN2O2 (II), crystallizes in the space group Pca21 with Z′ = 4 and it exhibits both pseudosymmetry and inversion twinning: a combination of six C—H⋯O and two C—H⋯π(arene) hydrogen bonds generate a three-dimensional assembly. In 1-(4-bromo­benzo­yl)-4-(2-meth­oxy­phen­yl)piperazine, C18H19BrN2O2 (III), which also crystallizes in space group Pca21 but with Z′ = 2, the bromo­benzoyl unit in one of the mol­ecules is disordered. Pseudosymmetry and inversion twinning are again present, and a combination of three C—H⋯O and one C—H⋯π(arene) hydrogen bonds generate a two-dimensional assembly. A single C—H⋯O hydrogen bond links the mol­ecules of 1-(4-iodo­benzo­yl)-4-(2-meth­oxy­phen­yl)piperazine, C18H19IN2O2 (IV), into simple chains but in the isomeric 3-iodo­benzoyl analogue (V), which crystallizes in space group P212121 with Z′ = 2, a two-dimensional assembly is generated by a combination of four C—H⋯O and two C—H⋯π(arene) hydrogen bonds; pseudosymmetry and inversion twinning are again present. A single C—H⋯O hydrogen bond links the mol­ecules of 1-(2-fluoro­benzo­yl)-4-(2-meth­oxy­phen­yl)piperazine, C18H19FN2O2 (VI), into simple chains. Comparisons are made with the structures of some related compounds.H center dot center dot center dot O and two C-H center dot center dot center dot pi(arene) hydrogen bonds generate a three-dimensional assembly. In 1-(4-bromobenzoyl)4-(2-methoxyphenyl)piperazine, C18H19BrN2O2 (III), which also crystallizes in space group Pca2(1) but with Z' = 2, the bromobenzoyl unit in one of the molecules is disordered. Pseudosymmetry and inversion twinning are again present, and a combination of three C-H···O and one C-H···π(arene) hydrogen bonds generate a two-dimensional assembly. A single C-H···O hydrogen bond links the molecules of 1-(4-iodobenzoyl)-4-(2-methoxyphenyl)piperazine, C18H19IN2O2 (IV), into simple chains but in the isomeric 3-iodobenzoyl analogue (V), which crystallizes in space group P212121 with Z' = 2, a two-dimensional assembly is generated by a combination of four C-H··· O and two C-H ···π(arene) hydrogen bonds; pseudosymmetry and inversion twinning are again present. A single C-H ···O hydrogen bond links the molecules of 1-(2-fluorobenzoyl)-4-(2-methoxyphenyl)piperazine, C18H19FN2O2 (VI), into simple chains. Comparisons are made with the structures of some related compounds.
dc.language.isoeng
dc.relation.ispartofActa Crystallographica Section E Crystallographic Communicationsen
dc.rightsCopyright © 2020 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.en
dc.subjectPiperazinesen
dc.subjectSynthesisen
dc.subjectCrystal structureen
dc.subjectMolecular conformationen
dc.subjectDisorderen
dc.subjectPseudosymmetryen
dc.subjectInversion twinningen
dc.subjectHydrogen bondingen
dc.subjectSupramolecular assemblyen
dc.subjectQD Chemistryen
dc.subjectDASen
dc.subject.lccQDen
dc.titleSix 1-halobenzoyl-4-(2-methoxyphenyl)piperazines having Z' values of one, two or four; disorder, pseudosymmetry, twinning and supramolecular assembly in one, two or three dimensionsen
dc.typeJournal articleen
dc.description.versionPublisher PDFen
dc.contributor.institutionUniversity of St Andrews.School of Chemistryen
dc.identifier.doihttps://doi.org/10.1107/S2056989020015649
dc.description.statusPeer revieweden


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