Three closely related 1-[(1,3-benzodioxol-5-yl)methyl]-4-(halobenzo­yl)piperazines: similar mol­ecular structures but different inter­molecular inter­actions

Mahesha, Ninganayaka and Sagar, B. K. and Yathirajan, H. S. and Furuya, Tetsundo and Haraguchi, Tomoyuki and Akitsu, Takashiro and Glidewell, Christopher (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, 75 (2). pp. 202-207. ISSN 1600-5368

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Official URL: https://doi.org/10.1107/S2056989019000458

Abstract

In each of the compounds 1-[(1,3-benzodioxol-5-yl)methyl]-4-(3-fluoro­benzo­yl)piperazine, C19H19FN2O3 (I), 1-[(1,3-benzodioxol-5-yl)methyl]-4-(2,6-di­fluoro­benzo­yl)piperazine, C19H18F2N2O3 (II), and 1-[(1,3-benzodioxol-5-yl)methyl]-4-(2,4-di­chloro­benzo­yl)piperazine, C19H19Cl2N2O3 (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.

Item Type: Article
Uncontrolled Keywords: piperazines, crystal structure, molecular conformation, hydrogen bonding, supramolecular assembly
Subjects: C Chemical Science > Chemistry
Divisions: Department of > Chemistry
Depositing User: MUL SWAPNA user
Date Deposited: 12 Oct 2019 10:32
Last Modified: 12 Oct 2019 10:32
URI: http://eprints.uni-mysore.ac.in/id/eprint/8948

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