Crystal structure of a mono-bridged calix[4]arene
The title compound, 52-[(5-bromopentyl)oxy]-12,114,35,55-tetra-tert-butyl-17,18,19,110-tetrahydro-16H,116H-1(4,12)-dibenzo[b,e][1,7]dioxacyclododecina-3,5(1,3)-dibenzenacyclohexaphan-32-ol, C54H73BrO4, was synthesized from the reaction of tert-butylcalix[4]arene with 1,5-dibromopentane using K2CO3 i...
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| Format: | Article |
| Language: | English |
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International Union of Crystallography
2015-07-01
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| Series: | Acta Crystallographica Section E: Crystallographic Communications |
| Subjects: | |
| Online Access: | http://scripts.iucr.org/cgi-bin/paper?S2056989015010932 |
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| author | Shimelis T. Hailu Ray J. Butcher Paul F. Hudrlik Anne M Hudrlik |
| author_facet | Shimelis T. Hailu Ray J. Butcher Paul F. Hudrlik Anne M Hudrlik |
| author_sort | Shimelis T. Hailu |
| collection | DOAJ |
| description | The title compound, 52-[(5-bromopentyl)oxy]-12,114,35,55-tetra-tert-butyl-17,18,19,110-tetrahydro-16H,116H-1(4,12)-dibenzo[b,e][1,7]dioxacyclododecina-3,5(1,3)-dibenzenacyclohexaphan-32-ol, C54H73BrO4, was synthesized from the reaction of tert-butylcalix[4]arene with 1,5-dibromopentane using K2CO3 in CH3CN. The structure consists of a calixarene unit with a five-carbon bridge connecting two proximal phenolic O atoms, and with a bromopentoxy chain on one of the remaining phenolic O atoms. The calixarene unit was found to have a flattened cone conformation with no solvent (or other guest) molecule observed in the cavity. Two of the opposite phenyl rings lean outwards with fold angles of 136.2 (1) and 133.0 (1)° between the rings and the plane of the bridging methylene C atoms, while the other two opposite rings form fold angles of 83.27 (9) and 105.46 (9)°. There is considerable disorder in this molecule. One of the tert-butyl groups is disordered over two conformations with occupancies of 0.527 (5) and 0.473 (5). The bromopentoxy chain is disordered over three configurations with occupancies of 0.418, 0.332 and 0.250. The five-carbon bridge connecting two proximal phenolic O atoms is disordered over two conformations with occupancies of 0.537 (7) and 0.463 (7). |
| first_indexed | 2024-12-20T11:21:21Z |
| format | Article |
| id | doaj.art-70ee449454aa4c9a9bdce666a07ab028 |
| institution | Directory Open Access Journal |
| issn | 2056-9890 |
| language | English |
| last_indexed | 2024-12-20T11:21:21Z |
| publishDate | 2015-07-01 |
| publisher | International Union of Crystallography |
| record_format | Article |
| series | Acta Crystallographica Section E: Crystallographic Communications |
| spelling | doaj.art-70ee449454aa4c9a9bdce666a07ab0282022-12-21T19:42:30ZengInternational Union of CrystallographyActa Crystallographica Section E: Crystallographic Communications2056-98902015-07-0171777277510.1107/S2056989015010932hg5441Crystal structure of a mono-bridged calix[4]areneShimelis T. Hailu0Ray J. Butcher1Paul F. Hudrlik2Anne M Hudrlik3Department of Chemistry, Howard University, 525 College Street NW, Washington, DC 20059, USADepartment of Chemistry, Howard University, 525 College Street NW, Washington, DC 20059, USADepartment of Chemistry, Howard University, 525 College Street NW, Washington, DC 20059, USADepartment of Chemistry, Howard University, 525 College Street NW, Washington, DC 20059, USAThe title compound, 52-[(5-bromopentyl)oxy]-12,114,35,55-tetra-tert-butyl-17,18,19,110-tetrahydro-16H,116H-1(4,12)-dibenzo[b,e][1,7]dioxacyclododecina-3,5(1,3)-dibenzenacyclohexaphan-32-ol, C54H73BrO4, was synthesized from the reaction of tert-butylcalix[4]arene with 1,5-dibromopentane using K2CO3 in CH3CN. The structure consists of a calixarene unit with a five-carbon bridge connecting two proximal phenolic O atoms, and with a bromopentoxy chain on one of the remaining phenolic O atoms. The calixarene unit was found to have a flattened cone conformation with no solvent (or other guest) molecule observed in the cavity. Two of the opposite phenyl rings lean outwards with fold angles of 136.2 (1) and 133.0 (1)° between the rings and the plane of the bridging methylene C atoms, while the other two opposite rings form fold angles of 83.27 (9) and 105.46 (9)°. There is considerable disorder in this molecule. One of the tert-butyl groups is disordered over two conformations with occupancies of 0.527 (5) and 0.473 (5). The bromopentoxy chain is disordered over three configurations with occupancies of 0.418, 0.332 and 0.250. The five-carbon bridge connecting two proximal phenolic O atoms is disordered over two conformations with occupancies of 0.537 (7) and 0.463 (7).http://scripts.iucr.org/cgi-bin/paper?S2056989015010932crystal structurecalix[4]arenebridged calix[4]areneflattened cone conformationbromopentoxy chainhydrogen bonding |
| spellingShingle | Shimelis T. Hailu Ray J. Butcher Paul F. Hudrlik Anne M Hudrlik Crystal structure of a mono-bridged calix[4]arene Acta Crystallographica Section E: Crystallographic Communications crystal structure calix[4]arene bridged calix[4]arene flattened cone conformation bromopentoxy chain hydrogen bonding |
| title | Crystal structure of a mono-bridged calix[4]arene |
| title_full | Crystal structure of a mono-bridged calix[4]arene |
| title_fullStr | Crystal structure of a mono-bridged calix[4]arene |
| title_full_unstemmed | Crystal structure of a mono-bridged calix[4]arene |
| title_short | Crystal structure of a mono-bridged calix[4]arene |
| title_sort | crystal structure of a mono bridged calix 4 arene |
| topic | crystal structure calix[4]arene bridged calix[4]arene flattened cone conformation bromopentoxy chain hydrogen bonding |
| url | http://scripts.iucr.org/cgi-bin/paper?S2056989015010932 |
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