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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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Date
01/02/2019
Author
Mahesha, Ninganayaka
Sagar, Belakavadi K.
Yathirajan, Hemmige S.
Furuya, Tetsundo
Haraguchi, Tomoyuki
Akitsu, Takashiro
Glidewell, Christopher
Keywords
Piperazines
Crystal structure
Molecular conformation
Hydrogen bonding
Supramolecular assembly
QD Chemistry
DAS
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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.
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
Publication
Acta Crystallographica Section E Crystallographic Communications
Status
Peer reviewed
DOI
https://doi.org/10.1107/S2056989019000458
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 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.
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  • University of St Andrews Research
URI
http://hdl.handle.net/10023/17045

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