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Three closely related 1-[(1,3-benzodioxol-5-yl)methyl]-4-(halobenzoyl)piperazines : similar molecular structures but different intermolecular interactions
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dc.contributor.author | Mahesha, Ninganayaka | |
dc.contributor.author | Sagar, Belakavadi K. | |
dc.contributor.author | Yathirajan, Hemmige S. | |
dc.contributor.author | Furuya, Tetsundo | |
dc.contributor.author | Haraguchi, Tomoyuki | |
dc.contributor.author | Akitsu, Takashiro | |
dc.contributor.author | Glidewell, Christopher | |
dc.date.accessioned | 2019-02-12T16:30:04Z | |
dc.date.available | 2019-02-12T16:30:04Z | |
dc.date.issued | 2019-02-01 | |
dc.identifier.citation | Mahesha , 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 . https://doi.org/10.1107/S2056989019000458 | en |
dc.identifier.issn | 2056-9890 | |
dc.identifier.other | PURE: 257718903 | |
dc.identifier.other | PURE UUID: 322f369a-6689-422b-9111-cf98f66d1ad9 | |
dc.identifier.other | crossref: 10.1107/S2056989019000458 | |
dc.identifier.other | Scopus: 85061119735 | |
dc.identifier.other | WOS: 000457717300021 | |
dc.identifier.uri | https://hdl.handle.net/10023/17045 | |
dc.description | HSY 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.abstract | In 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.language.iso | eng | |
dc.relation.ispartof | Acta Crystallographica Section E Crystallographic Communications | en |
dc.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. | en |
dc.subject | Piperazines | en |
dc.subject | Crystal structure | en |
dc.subject | Molecular conformation | en |
dc.subject | Hydrogen bonding | en |
dc.subject | Supramolecular assembly | en |
dc.subject | QD Chemistry | en |
dc.subject | DAS | en |
dc.subject.lcc | QD | en |
dc.title | Three closely related 1-[(1,3-benzodioxol-5-yl)methyl]-4-(halobenzoyl)piperazines : similar molecular structures but different intermolecular interactions | en |
dc.type | Journal article | en |
dc.description.version | Publisher PDF | en |
dc.contributor.institution | University of St Andrews. School of Chemistry | en |
dc.identifier.doi | https://doi.org/10.1107/S2056989019000458 | |
dc.description.status | Peer reviewed | en |
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