Three closely related 1-[(1,3-benzodioxol-5-yl)methyl]-4-(halobenzoyl)piperazines : similar molecular structures but different intermolecular interactions
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
ISSN
2056-9890Type
Journal article
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.Collections
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