A very short O—H...O hydrogen bond in the structure of clozapinium hydrogen bis(3,5-dinitrobenzoate)
In the title salt {systematic name: 4-[6-chloro-2,9-diazatricyclo[9.4.0.03,8]pentadeca-1(15),3(8),4,6,9,11,13-heptaen-10-yl]-1-methylpiperazin-1-ium 3,5-dinitrobenzoate–3,5-dinitrobenzic acid (1/1)}, C18H20ClN4+·C7H3N2O6−·C7H4N2O6, there is a very short, asymmetric, O—H...O hydrogen bond [O...O = 2....
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| Format: | Article |
| Language: | English |
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International Union of Crystallography
2020-10-01
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| Series: | Acta Crystallographica Section E: Crystallographic Communications |
| Subjects: | |
| Online Access: | http://scripts.iucr.org/cgi-bin/paper?S2056989020012268 |
| _version_ | 1818488312270159872 |
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| author | Mohammed A. E. Shaibah Channappa N. Kavitha Hemmige S. Yathirajan Sabine Foro Christopher Glidewell |
| author_facet | Mohammed A. E. Shaibah Channappa N. Kavitha Hemmige S. Yathirajan Sabine Foro Christopher Glidewell |
| author_sort | Mohammed A. E. Shaibah |
| collection | DOAJ |
| description | In the title salt {systematic name: 4-[6-chloro-2,9-diazatricyclo[9.4.0.03,8]pentadeca-1(15),3(8),4,6,9,11,13-heptaen-10-yl]-1-methylpiperazin-1-ium 3,5-dinitrobenzoate–3,5-dinitrobenzic acid (1/1)}, C18H20ClN4+·C7H3N2O6−·C7H4N2O6, there is a very short, asymmetric, O—H...O hydrogen bond [O...O = 2.453 (3) Å] within the anion. The oxygen atoms of one of the nitro groups of the anion are disordered over two sets of sites having occupancies of 0.56 (3) and 0.44 (3). The fused tricyclic portion of the cation adopts a butterfly conformation, with a dihedral angle of 45.59 (6)° between the planes of the two aryl rings. In the crystal, a combination of O—H...O, N—H...O and C—H...O hydrogen bonds links the component species into a three-dimensional framework. Comparisons are made with the structures of some related compounds. |
| first_indexed | 2024-12-10T16:49:19Z |
| format | Article |
| id | doaj.art-916d99523c864f5fa53b9200596b5157 |
| institution | Directory Open Access Journal |
| issn | 2056-9890 |
| language | English |
| last_indexed | 2024-12-10T16:49:19Z |
| publishDate | 2020-10-01 |
| publisher | International Union of Crystallography |
| record_format | Article |
| series | Acta Crystallographica Section E: Crystallographic Communications |
| spelling | doaj.art-916d99523c864f5fa53b9200596b51572022-12-22T01:40:57ZengInternational Union of CrystallographyActa Crystallographica Section E: Crystallographic Communications2056-98902020-10-0176101629163310.1107/S2056989020012268hb7944A very short O—H...O hydrogen bond in the structure of clozapinium hydrogen bis(3,5-dinitrobenzoate)Mohammed A. E. Shaibah0Channappa N. Kavitha1Hemmige S. Yathirajan2Sabine Foro3Christopher Glidewell4Department of Studies in Chemistry, University of Mysore, Manasagangotri, Mysuru 570 006, IndiaDepartment of Chemistry, Maharani's Science College for Women, Mysuru 570 001, IndiaDepartment of Studies in Chemistry, University of Mysore, Manasagangotri, Mysuru 570 006, IndiaInstitute of Materials Science, Darmstadt University of Technology, Alarich-Weiss-Strasse 2, D-64287 Darmstadt, GermanySchool of Chemistry, University of St Andrews, St Andrews, Fife KY16 9ST, UKIn the title salt {systematic name: 4-[6-chloro-2,9-diazatricyclo[9.4.0.03,8]pentadeca-1(15),3(8),4,6,9,11,13-heptaen-10-yl]-1-methylpiperazin-1-ium 3,5-dinitrobenzoate–3,5-dinitrobenzic acid (1/1)}, C18H20ClN4+·C7H3N2O6−·C7H4N2O6, there is a very short, asymmetric, O—H...O hydrogen bond [O...O = 2.453 (3) Å] within the anion. The oxygen atoms of one of the nitro groups of the anion are disordered over two sets of sites having occupancies of 0.56 (3) and 0.44 (3). The fused tricyclic portion of the cation adopts a butterfly conformation, with a dihedral angle of 45.59 (6)° between the planes of the two aryl rings. In the crystal, a combination of O—H...O, N—H...O and C—H...O hydrogen bonds links the component species into a three-dimensional framework. Comparisons are made with the structures of some related compounds.http://scripts.iucr.org/cgi-bin/paper?S2056989020012268clozapinecrystal structuremolecular conformationhydrogen bondingvery short hydrogen bondssupramolecular assembly |
| spellingShingle | Mohammed A. E. Shaibah Channappa N. Kavitha Hemmige S. Yathirajan Sabine Foro Christopher Glidewell A very short O—H...O hydrogen bond in the structure of clozapinium hydrogen bis(3,5-dinitrobenzoate) Acta Crystallographica Section E: Crystallographic Communications clozapine crystal structure molecular conformation hydrogen bonding very short hydrogen bonds supramolecular assembly |
| title | A very short O—H...O hydrogen bond in the structure of clozapinium hydrogen bis(3,5-dinitrobenzoate) |
| title_full | A very short O—H...O hydrogen bond in the structure of clozapinium hydrogen bis(3,5-dinitrobenzoate) |
| title_fullStr | A very short O—H...O hydrogen bond in the structure of clozapinium hydrogen bis(3,5-dinitrobenzoate) |
| title_full_unstemmed | A very short O—H...O hydrogen bond in the structure of clozapinium hydrogen bis(3,5-dinitrobenzoate) |
| title_short | A very short O—H...O hydrogen bond in the structure of clozapinium hydrogen bis(3,5-dinitrobenzoate) |
| title_sort | very short o h o hydrogen bond in the structure of clozapinium hydrogen bis 3 5 dinitrobenzoate |
| topic | clozapine crystal structure molecular conformation hydrogen bonding very short hydrogen bonds supramolecular assembly |
| url | http://scripts.iucr.org/cgi-bin/paper?S2056989020012268 |
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