Three closely related 1-[(1,3-benzodioxol-5-yl)methyl]-4-(halobenzoyl)piperazines: similar molecular structures but different intermolecular interactions
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...
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| Format: | Article |
| Language: | English |
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International Union of Crystallography
2019-02-01
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| Series: | Acta Crystallographica Section E: Crystallographic Communications |
| Subjects: | |
| Online Access: | http://scripts.iucr.org/cgi-bin/paper?S2056989019000458 |
| _version_ | 1798026934250110976 |
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| author | Ninganayaka Mahesha Belakavadi K. Sagar Hemmige S. Yathirajan Tetsundo Furuya Tomoyuki Haraguchi Takashiro Akitsu Christopher Glidewell |
| author_facet | Ninganayaka Mahesha Belakavadi K. Sagar Hemmige S. Yathirajan Tetsundo Furuya Tomoyuki Haraguchi Takashiro Akitsu Christopher Glidewell |
| author_sort | Ninganayaka Mahesha |
| collection | DOAJ |
| description | 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. |
| first_indexed | 2024-04-11T18:43:10Z |
| format | Article |
| id | doaj.art-a685481be94d44388d81b0cfd404e4e7 |
| institution | Directory Open Access Journal |
| issn | 2056-9890 |
| language | English |
| last_indexed | 2024-04-11T18:43:10Z |
| publishDate | 2019-02-01 |
| publisher | International Union of Crystallography |
| record_format | Article |
| series | Acta Crystallographica Section E: Crystallographic Communications |
| spelling | doaj.art-a685481be94d44388d81b0cfd404e4e72022-12-22T04:08:54ZengInternational Union of CrystallographyActa Crystallographica Section E: Crystallographic Communications2056-98902019-02-0175220220710.1107/S2056989019000458zl2747Three closely related 1-[(1,3-benzodioxol-5-yl)methyl]-4-(halobenzoyl)piperazines: similar molecular structures but different intermolecular interactionsNinganayaka Mahesha0Belakavadi K. Sagar1Hemmige S. Yathirajan2Tetsundo Furuya3Tomoyuki Haraguchi4Takashiro Akitsu5Christopher Glidewell6Department of Studies in Chemistry, University of Mysore, Manasagangotri, Mysuru-570 006, IndiaDepartment of Studies in Chemistry, University of Mysore, Manasagangotri, Mysuru-570 006, IndiaDepartment of Studies in Chemistry, University of Mysore, Manasagangotri, Mysuru-570 006, IndiaDepartment of Chemistry, Faculty of Science, Tokyo University of Science, 1-3 Kagurazaka, Shinjuku-ku, Tokyo 162-8601, JapanDepartment of Chemistry, Faculty of Science, Tokyo University of Science, 1-3 Kagurazaka, Shinjuku-ku, Tokyo 162-8601, JapanDepartment of Chemistry, Faculty of Science, Tokyo University of Science, 1-3 Kagurazaka, Shinjuku-ku, Tokyo 162-8601, JapanSchool of Chemistry, University of St Andrews, St Andrews, Fife KY16 9ST, UKIn 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.http://scripts.iucr.org/cgi-bin/paper?S2056989019000458piperazinescrystal structuremolecular conformationhydrogen bondingsupramolecular assembly |
| spellingShingle | Ninganayaka Mahesha Belakavadi K. Sagar Hemmige S. Yathirajan Tetsundo Furuya Tomoyuki Haraguchi Takashiro Akitsu Christopher Glidewell 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 piperazines crystal structure molecular conformation hydrogen bonding supramolecular assembly |
| title | Three closely related 1-[(1,3-benzodioxol-5-yl)methyl]-4-(halobenzoyl)piperazines: similar molecular structures but different intermolecular interactions |
| title_full | Three closely related 1-[(1,3-benzodioxol-5-yl)methyl]-4-(halobenzoyl)piperazines: similar molecular structures but different intermolecular interactions |
| title_fullStr | Three closely related 1-[(1,3-benzodioxol-5-yl)methyl]-4-(halobenzoyl)piperazines: similar molecular structures but different intermolecular interactions |
| title_full_unstemmed | Three closely related 1-[(1,3-benzodioxol-5-yl)methyl]-4-(halobenzoyl)piperazines: similar molecular structures but different intermolecular interactions |
| title_short | Three closely related 1-[(1,3-benzodioxol-5-yl)methyl]-4-(halobenzoyl)piperazines: similar molecular structures but different intermolecular interactions |
| title_sort | three closely related 1 1 3 benzodioxol 5 yl methyl 4 halobenzoyl piperazines similar molecular structures but different intermolecular interactions |
| topic | piperazines crystal structure molecular conformation hydrogen bonding supramolecular assembly |
| url | http://scripts.iucr.org/cgi-bin/paper?S2056989019000458 |
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