Bis(benzyltrimethylammonium) bis[(4SR,12SR,18RS,26RS)-4,18,26-trihydroxy-12-oxido-13,17-dioxaheptacyclo[14.10.0.03,14.04,12.06,11.018,26.019,24]hexacosa-1,3(14),6,8,10,15,19,21,23-nonaene-5,25-dione] sesquihydrate: dimeric structure formation via [O—H—O]−negative charge-assisted hydrogen bonds (–CAHB) with benzyltrimethylammonium counter-ions
The reaction between bis-ninhydrin resorcinol and benzyltrimethylammonium fluoride in ethanol has produced the title compound, 2C10H16N+·2C24H13O8−·1.5H2O, which contains a unique centrosymmetric supramolecular dimeric entity, where two deprotonated ligands are held together via two strong and short...
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| Format: | Article |
| Language: | English |
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International Union of Crystallography
2016-03-01
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| Series: | Acta Crystallographica Section E: Crystallographic Communications |
| Subjects: | |
| Online Access: | http://scripts.iucr.org/cgi-bin/paper?S2056989016002899 |
| _version_ | 1819290739575619584 |
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| author | Ravell Bengiat Maayan Gil Asne Klein Benny Bogoslavsky Shmuel Cohen Joseph Almog |
| author_facet | Ravell Bengiat Maayan Gil Asne Klein Benny Bogoslavsky Shmuel Cohen Joseph Almog |
| author_sort | Ravell Bengiat |
| collection | DOAJ |
| description | The reaction between bis-ninhydrin resorcinol and benzyltrimethylammonium fluoride in ethanol has produced the title compound, 2C10H16N+·2C24H13O8−·1.5H2O, which contains a unique centrosymmetric supramolecular dimeric entity, where two deprotonated ligands are held together via two strong and short [O...O = 2.4395 (13) Å] [O—H—O]− bonds of the type negative charge-assisted hydrogen bonds (–CAHB). The central aromatic rings of the ligands create parallel-displaced π–π stacking at an interplanar distance of 3.381 (1) Å, which helps stabilize the dimer. In the crystal, two symmetry-related solvent water molecules with a site occupancy of 0.75 are attached to the carbonyl groups of the dimer by weaker O—H...O hydrogen bonds, forming chains along [101]. |
| first_indexed | 2024-12-24T03:27:32Z |
| format | Article |
| id | doaj.art-a22dbda5e4b2400e89938d8f55901ea6 |
| institution | Directory Open Access Journal |
| issn | 2056-9890 |
| language | English |
| last_indexed | 2024-12-24T03:27:32Z |
| publishDate | 2016-03-01 |
| publisher | International Union of Crystallography |
| record_format | Article |
| series | Acta Crystallographica Section E: Crystallographic Communications |
| spelling | doaj.art-a22dbda5e4b2400e89938d8f55901ea62022-12-21T17:17:18ZengInternational Union of CrystallographyActa Crystallographica Section E: Crystallographic Communications2056-98902016-03-0172339940210.1107/S2056989016002899lh5804Bis(benzyltrimethylammonium) bis[(4SR,12SR,18RS,26RS)-4,18,26-trihydroxy-12-oxido-13,17-dioxaheptacyclo[14.10.0.03,14.04,12.06,11.018,26.019,24]hexacosa-1,3(14),6,8,10,15,19,21,23-nonaene-5,25-dione] sesquihydrate: dimeric structure formation via [O—H—O]−negative charge-assisted hydrogen bonds (–CAHB) with benzyltrimethylammonium counter-ionsRavell Bengiat0Maayan Gil1Asne Klein2Benny Bogoslavsky3Shmuel Cohen4Joseph Almog5The Institute of Chemistry, The Hebrew University of Jerusalem, Jerusalem, 9190401, IsraelThe Institute of Chemistry, The Hebrew University of Jerusalem, Jerusalem, 9190401, IsraelThe Institute of Chemistry, The Hebrew University of Jerusalem, Jerusalem, 9190401, IsraelThe Institute of Chemistry, The Hebrew University of Jerusalem, Jerusalem, 9190401, IsraelThe Institute of Chemistry, The Hebrew University of Jerusalem, Jerusalem, 9190401, IsraelThe Institute of Chemistry, The Hebrew University of Jerusalem, Jerusalem, 9190401, IsraelThe reaction between bis-ninhydrin resorcinol and benzyltrimethylammonium fluoride in ethanol has produced the title compound, 2C10H16N+·2C24H13O8−·1.5H2O, which contains a unique centrosymmetric supramolecular dimeric entity, where two deprotonated ligands are held together via two strong and short [O...O = 2.4395 (13) Å] [O—H—O]− bonds of the type negative charge-assisted hydrogen bonds (–CAHB). The central aromatic rings of the ligands create parallel-displaced π–π stacking at an interplanar distance of 3.381 (1) Å, which helps stabilize the dimer. In the crystal, two symmetry-related solvent water molecules with a site occupancy of 0.75 are attached to the carbonyl groups of the dimer by weaker O—H...O hydrogen bonds, forming chains along [101].http://scripts.iucr.org/cgi-bin/paper?S2056989016002899crystal structurevasarenenegative charge-assisted hydrogen bond [(−)CAHB]supramolecular dimerninhydrin |
| spellingShingle | Ravell Bengiat Maayan Gil Asne Klein Benny Bogoslavsky Shmuel Cohen Joseph Almog Bis(benzyltrimethylammonium) bis[(4SR,12SR,18RS,26RS)-4,18,26-trihydroxy-12-oxido-13,17-dioxaheptacyclo[14.10.0.03,14.04,12.06,11.018,26.019,24]hexacosa-1,3(14),6,8,10,15,19,21,23-nonaene-5,25-dione] sesquihydrate: dimeric structure formation via [O—H—O]−negative charge-assisted hydrogen bonds (–CAHB) with benzyltrimethylammonium counter-ions Acta Crystallographica Section E: Crystallographic Communications crystal structure vasarene negative charge-assisted hydrogen bond [(−)CAHB] supramolecular dimer ninhydrin |
| title | Bis(benzyltrimethylammonium) bis[(4SR,12SR,18RS,26RS)-4,18,26-trihydroxy-12-oxido-13,17-dioxaheptacyclo[14.10.0.03,14.04,12.06,11.018,26.019,24]hexacosa-1,3(14),6,8,10,15,19,21,23-nonaene-5,25-dione] sesquihydrate: dimeric structure formation via [O—H—O]−negative charge-assisted hydrogen bonds (–CAHB) with benzyltrimethylammonium counter-ions |
| title_full | Bis(benzyltrimethylammonium) bis[(4SR,12SR,18RS,26RS)-4,18,26-trihydroxy-12-oxido-13,17-dioxaheptacyclo[14.10.0.03,14.04,12.06,11.018,26.019,24]hexacosa-1,3(14),6,8,10,15,19,21,23-nonaene-5,25-dione] sesquihydrate: dimeric structure formation via [O—H—O]−negative charge-assisted hydrogen bonds (–CAHB) with benzyltrimethylammonium counter-ions |
| title_fullStr | Bis(benzyltrimethylammonium) bis[(4SR,12SR,18RS,26RS)-4,18,26-trihydroxy-12-oxido-13,17-dioxaheptacyclo[14.10.0.03,14.04,12.06,11.018,26.019,24]hexacosa-1,3(14),6,8,10,15,19,21,23-nonaene-5,25-dione] sesquihydrate: dimeric structure formation via [O—H—O]−negative charge-assisted hydrogen bonds (–CAHB) with benzyltrimethylammonium counter-ions |
| title_full_unstemmed | Bis(benzyltrimethylammonium) bis[(4SR,12SR,18RS,26RS)-4,18,26-trihydroxy-12-oxido-13,17-dioxaheptacyclo[14.10.0.03,14.04,12.06,11.018,26.019,24]hexacosa-1,3(14),6,8,10,15,19,21,23-nonaene-5,25-dione] sesquihydrate: dimeric structure formation via [O—H—O]−negative charge-assisted hydrogen bonds (–CAHB) with benzyltrimethylammonium counter-ions |
| title_short | Bis(benzyltrimethylammonium) bis[(4SR,12SR,18RS,26RS)-4,18,26-trihydroxy-12-oxido-13,17-dioxaheptacyclo[14.10.0.03,14.04,12.06,11.018,26.019,24]hexacosa-1,3(14),6,8,10,15,19,21,23-nonaene-5,25-dione] sesquihydrate: dimeric structure formation via [O—H—O]−negative charge-assisted hydrogen bonds (–CAHB) with benzyltrimethylammonium counter-ions |
| title_sort | bis benzyltrimethylammonium bis 4sr 12sr 18rs 26rs 4 18 26 trihydroxy 12 oxido 13 17 dioxaheptacyclo 14 10 0 03 14 04 12 06 11 018 26 019 24 hexacosa 1 3 14 6 8 10 15 19 21 23 nonaene 5 25 dione sesquihydrate dimeric structure formation via o h o negative charge assisted hydrogen bonds cahb with benzyltrimethylammonium counter ions |
| topic | crystal structure vasarene negative charge-assisted hydrogen bond [(−)CAHB] supramolecular dimer ninhydrin |
| url | http://scripts.iucr.org/cgi-bin/paper?S2056989016002899 |
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