Six 1-aroyl-4-(4-methoxyphenyl)piperazines: similar molecular structures but different patterns of supramolecular assembly
Six new 1-aroyl-4-(4-methoxyphenyl)piperazines have been prepared, using coupling reactions between benzoic acids and N-(4-methoxyphenyl)piperazine. There are no significant hydrogen bonds in the structure of 1-benzoyl-4-(4-methoxyphenyl)piperazine, C18H20N2O2, (I). The molecules of 1-(2-fluorobenzo...
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| Format: | Article |
| Language: | English |
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International Union of Crystallography
2019-08-01
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| Series: | Acta Crystallographica Section E: Crystallographic Communications |
| Subjects: | |
| Online Access: | http://scripts.iucr.org/cgi-bin/paper?S2056989019010491 |
| _version_ | 1798030835816857600 |
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| author | Haruvegowda Kiran Kumar Hemmige S. Yathirajan Belakavadi K. Sagar Sabine Foro Christopher Glidewell |
| author_facet | Haruvegowda Kiran Kumar Hemmige S. Yathirajan Belakavadi K. Sagar Sabine Foro Christopher Glidewell |
| author_sort | Haruvegowda Kiran Kumar |
| collection | DOAJ |
| description | Six new 1-aroyl-4-(4-methoxyphenyl)piperazines have been prepared, using coupling reactions between benzoic acids and N-(4-methoxyphenyl)piperazine. There are no significant hydrogen bonds in the structure of 1-benzoyl-4-(4-methoxyphenyl)piperazine, C18H20N2O2, (I). The molecules of 1-(2-fluorobenzoyl)-4-(4-methoxyphenyl)piperazine, C18H19FN2O2, (II), are linked by two C—H...O hydrogen bonds to form chains of rings, which are linked into sheets by an aromatic π–π stacking interaction. 1-(2-Chlorobenzoyl)-4-(4-methoxyphenyl)piperazine, C18H19ClN2O2, (III), 1-(2-bromobenzoyl)-4-(4-methoxyphenyl)piperazine, C18H19BrN2O2, (IV), and 1-(2-iodobenzoyl)-4-(4-methoxyphenyl)piperazine, C18H19IN2O2, (V), are isomorphous, but in (III) the aroyl ring is disordered over two sets of atomic sites having occupancies of 0.942 (2) and 0.058 (2). In each of (III)–(V), a combination of two C—H...π(arene) hydrogen bonds links the molecules into sheets. A single O—H...O hydrogen bond links the molecules of 1-(2-hydroxybenzoyl)-4-(4-methoxyphenyl)piperazine, C18H20N2O3, (VI), into simple chains. Comparisons are made with the structures of some related compounds. |
| first_indexed | 2024-04-11T19:46:34Z |
| format | Article |
| id | doaj.art-f7710b0413f74483be1a832275a9bf2d |
| institution | Directory Open Access Journal |
| issn | 2056-9890 |
| language | English |
| last_indexed | 2024-04-11T19:46:34Z |
| publishDate | 2019-08-01 |
| publisher | International Union of Crystallography |
| record_format | Article |
| series | Acta Crystallographica Section E: Crystallographic Communications |
| spelling | doaj.art-f7710b0413f74483be1a832275a9bf2d2022-12-22T04:06:27ZengInternational Union of CrystallographyActa Crystallographica Section E: Crystallographic Communications2056-98902019-08-017581253126010.1107/S2056989019010491zl2757Six 1-aroyl-4-(4-methoxyphenyl)piperazines: similar molecular structures but different patterns of supramolecular assemblyHaruvegowda Kiran Kumar0Hemmige S. Yathirajan1Belakavadi K. Sagar2Sabine Foro3Christopher Glidewell4Department 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, Mysore-570 006, IndiaInstitute of Materials Science, Darmstadt University of Technology, Petersenstrasse 23, D-64287 Darmstadt, GermanySchool of Chemistry, University of St Andrews, St Andrews, Fife KY16 9ST, ScotlandSix new 1-aroyl-4-(4-methoxyphenyl)piperazines have been prepared, using coupling reactions between benzoic acids and N-(4-methoxyphenyl)piperazine. There are no significant hydrogen bonds in the structure of 1-benzoyl-4-(4-methoxyphenyl)piperazine, C18H20N2O2, (I). The molecules of 1-(2-fluorobenzoyl)-4-(4-methoxyphenyl)piperazine, C18H19FN2O2, (II), are linked by two C—H...O hydrogen bonds to form chains of rings, which are linked into sheets by an aromatic π–π stacking interaction. 1-(2-Chlorobenzoyl)-4-(4-methoxyphenyl)piperazine, C18H19ClN2O2, (III), 1-(2-bromobenzoyl)-4-(4-methoxyphenyl)piperazine, C18H19BrN2O2, (IV), and 1-(2-iodobenzoyl)-4-(4-methoxyphenyl)piperazine, C18H19IN2O2, (V), are isomorphous, but in (III) the aroyl ring is disordered over two sets of atomic sites having occupancies of 0.942 (2) and 0.058 (2). In each of (III)–(V), a combination of two C—H...π(arene) hydrogen bonds links the molecules into sheets. A single O—H...O hydrogen bond links the molecules of 1-(2-hydroxybenzoyl)-4-(4-methoxyphenyl)piperazine, C18H20N2O3, (VI), into simple chains. Comparisons are made with the structures of some related compounds.http://scripts.iucr.org/cgi-bin/paper?S2056989019010491piperazinescrystal structureisomorphismdisorderhydrogen bondingsupramolecular assembly |
| spellingShingle | Haruvegowda Kiran Kumar Hemmige S. Yathirajan Belakavadi K. Sagar Sabine Foro Christopher Glidewell Six 1-aroyl-4-(4-methoxyphenyl)piperazines: similar molecular structures but different patterns of supramolecular assembly Acta Crystallographica Section E: Crystallographic Communications piperazines crystal structure isomorphism disorder hydrogen bonding supramolecular assembly |
| title | Six 1-aroyl-4-(4-methoxyphenyl)piperazines: similar molecular structures but different patterns of supramolecular assembly |
| title_full | Six 1-aroyl-4-(4-methoxyphenyl)piperazines: similar molecular structures but different patterns of supramolecular assembly |
| title_fullStr | Six 1-aroyl-4-(4-methoxyphenyl)piperazines: similar molecular structures but different patterns of supramolecular assembly |
| title_full_unstemmed | Six 1-aroyl-4-(4-methoxyphenyl)piperazines: similar molecular structures but different patterns of supramolecular assembly |
| title_short | Six 1-aroyl-4-(4-methoxyphenyl)piperazines: similar molecular structures but different patterns of supramolecular assembly |
| title_sort | six 1 aroyl 4 4 methoxyphenyl piperazines similar molecular structures but different patterns of supramolecular assembly |
| topic | piperazines crystal structure isomorphism disorder hydrogen bonding supramolecular assembly |
| url | http://scripts.iucr.org/cgi-bin/paper?S2056989019010491 |
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