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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.othercrossref: 10.1107/S2056989019000458
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.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.contributor.institutionUniversity of St Andrews. School of Chemistryen
dc.description.statusPeer revieweden

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