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dc.contributor.authorMahesha, Ninganayaka
dc.contributor.authorSagar, Belakavadi K.
dc.contributor.authorYathirajan, Hemmige S.
dc.contributor.authorFuruya, Tetsundo
dc.contributor.authorHaraguchi, Tomoyuki
dc.contributor.authorAkitsu, Takashiro
dc.contributor.authorGlidewell, Christopher
dc.identifier.citationMahesha , N , Sagar , B K , Yathirajan , H S , Furuya , T , Haraguchi , T , Akitsu , T & Glidewell , C 2019 , ' Three closely related 1-[(1,3-benzodioxol-5-yl)methyl]-4-(halobenzoyl)piperazines : similar molecular structures but different intermolecular interactions ' , Acta Crystallographica Section E Crystallographic Communications , vol. 75 , no. 2 , pp. 202-207 .
dc.identifier.otherPURE: 257718903
dc.identifier.otherPURE UUID: 322f369a-6689-422b-9111-cf98f66d1ad9
dc.identifier.othercrossref: 10.1107/S2056989019000458
dc.identifier.otherScopus: 85061119735
dc.identifier.otherWOS: 000457717300021
dc.descriptionHSY is grateful to the UGC, New Delhi for the award of a BSR Faculty Fellowship for three years. BKS thanks the UGC for the award of a Rajeev Gandhi Fellowship.en
dc.description.abstractIn each of the compounds 1-[(1,3-benzodioxol-5-yl)methyl]-4-(3-fluoro­benzo­yl)piperazine, C19H 19FN 2O 3 (I), 1-[(1,3-benzodioxol-5-yl)methyl]-4-(2,6-di­fluoro­benzo­yl)piperazine, C19H 18F 2N 2O 3 (II), and 1-[(1,3-benzodioxol-5-yl)methyl]-4-(2,4-di­chloro­benzo­yl)piperazine, C19H 19Cl 2N 2O 3 (III), the piperazine rings adopt a chair conformation with the (1,3-benzodioxol-5-yl)methyl substituent occupying an equatorial site: the five-membered rings are all slightly folded across the O⋯O line leading to envelope conformations. The dihedral angle between the planar amidic fragment and the haloaryl ring is 62.97 (5)° in (I) but 77.72 (12)° and 75.50 (5)° in (II) and (III), respectively. Despite their similarity in constitution and conformation, the supra­molecular inter­actions in (I)–(III) differ: in (I), a combination of C—H⋯O and C—H⋯π(arene) hydrogen bonds links the mol­ecules into a three-dimensional framework structure, but there are no hydrogen bonds of any sort in either (II) or (III), although the structure of (III) contains a short Cl⋯Cl contact between inversion-related pairs of mol­ecules.
dc.relation.ispartofActa Crystallographica Section E Crystallographic Communicationsen
dc.rightsCopyright © 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.en
dc.subjectCrystal structureen
dc.subjectMolecular conformationen
dc.subjectHydrogen bondingen
dc.subjectSupramolecular assemblyen
dc.subjectQD Chemistryen
dc.titleThree closely related 1-[(1,3-benzodioxol-5-yl)methyl]-4-(halobenzoyl)piperazines : similar molecular structures but different intermolecular interactionsen
dc.typeJournal articleen
dc.description.versionPublisher PDFen
dc.contributor.institutionUniversity of St Andrews.School of Chemistryen
dc.description.statusPeer revieweden

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