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Three closely related 1-[(1,3-benzodioxol-5-yl)-methyl]-4-(halobenzoyl)piperazines: similar molecular structures but different intermolecular interactions.
- Source :
-
Acta Crystallographica Section E: Crystallographic Communications . Feb2019, Vol. 75 Issue 2, p202-207. 6p. - Publication Year :
- 2019
-
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. [ABSTRACT FROM AUTHOR]
- Subjects :
- *PIPERAZINE
*CRYSTAL structure
*INTERMOLECULAR interactions
Subjects
Details
- Language :
- English
- ISSN :
- 20569890
- Volume :
- 75
- Issue :
- 2
- Database :
- Academic Search Index
- Journal :
- Acta Crystallographica Section E: Crystallographic Communications
- Publication Type :
- Academic Journal
- Accession number :
- 134590571
- Full Text :
- https://doi.org/10.1107/S2056989019000458