Iclaprim mesylate displaying a hydrogen-bonded molecular tape
The title compound, 2,6-diamino-5-[(2-cyclopropyl-7,8-dimethoxy-2H-1-benzopyran-5-yl)methyl]pyrimidin-1-ium methanesulfonate, C19H23N4O3+·CH3O3S−, is a salt made up from a protonated iclaprim molecule and a mesylate anion. The pyrimidine and chromene units of the iclaprim molecule form an orthogonal...
| Main Authors: | , , , , , , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
International Union of Crystallography
2023-01-01
|
| Series: | Acta Crystallographica Section E: Crystallographic Communications |
| Subjects: | |
| Online Access: | http://scripts.iucr.org/cgi-bin/paper?S2056989022011689 |
| _version_ | 1797960476373549056 |
|---|---|
| author | Sandro Neuner Thomas Gelbrich Klaus Wurst Josef Spreitz Sven Nerdinger Ulrich J. Griesser Marijan Stefinovic Herwig Schottenberger |
| author_facet | Sandro Neuner Thomas Gelbrich Klaus Wurst Josef Spreitz Sven Nerdinger Ulrich J. Griesser Marijan Stefinovic Herwig Schottenberger |
| author_sort | Sandro Neuner |
| collection | DOAJ |
| description | The title compound, 2,6-diamino-5-[(2-cyclopropyl-7,8-dimethoxy-2H-1-benzopyran-5-yl)methyl]pyrimidin-1-ium methanesulfonate, C19H23N4O3+·CH3O3S−, is a salt made up from a protonated iclaprim molecule and a mesylate anion. The pyrimidine and chromene units of the iclaprim molecule form an orthogonal arrangement [interplanar angle of 89.67 (6)°], and the 3-nitrogen position of the pyrimidine ring is protonated. Four distinct N—H...O interactions and an additional N—H...N hydrogen bond connect iclaprim and mesylate molecules to one another, resulting in an infinite hydrogen-bonded molecular tape structure. The central section of the tape is formed by a sequence of fused hydrogen-bonded rings involving four distinct ring types. |
| first_indexed | 2024-04-11T00:45:41Z |
| format | Article |
| id | doaj.art-5bc27a2348674a28bf708c52269f20a8 |
| institution | Directory Open Access Journal |
| issn | 2056-9890 |
| language | English |
| last_indexed | 2024-04-11T00:45:41Z |
| publishDate | 2023-01-01 |
| publisher | International Union of Crystallography |
| record_format | Article |
| series | Acta Crystallographica Section E: Crystallographic Communications |
| spelling | doaj.art-5bc27a2348674a28bf708c52269f20a82023-01-05T15:20:36ZengInternational Union of CrystallographyActa Crystallographica Section E: Crystallographic Communications2056-98902023-01-01791242710.1107/S2056989022011689wm5666Iclaprim mesylate displaying a hydrogen-bonded molecular tapeSandro Neuner0Thomas Gelbrich1Klaus Wurst2Josef Spreitz3Sven Nerdinger4Ulrich J. Griesser5Marijan Stefinovic6Herwig Schottenberger7University of Innsbruck, Department of General, Inorganic and Theoretical Chemistry, Innrain 80-82, 6020 Innsbruck, AustriaUniversity of Innsbruck, Institute of Pharmacy, Innrain 52, 6020 Innsbruck, AustriaUniversity of Innsbruck, Department of General, Inorganic and Theoretical Chemistry, Innrain 80-82, 6020 Innsbruck, AustriaAglycon Dr. Spreitz KG, Europapark 1, A-8412 Allerheiligen b. Wildon, AustriaSandoz GmbH, Biochemiestrasse 10, 6250 Kundl, AustriaUniversity of Innsbruck, Institute of Pharmacy, Innrain 52, 6020 Innsbruck, AustriaSandoz GmbH, Biochemiestrasse 10, 6250 Kundl, AustriaUniversity of Innsbruck, Department of General, Inorganic and Theoretical Chemistry, Innrain 80-82, 6020 Innsbruck, AustriaThe title compound, 2,6-diamino-5-[(2-cyclopropyl-7,8-dimethoxy-2H-1-benzopyran-5-yl)methyl]pyrimidin-1-ium methanesulfonate, C19H23N4O3+·CH3O3S−, is a salt made up from a protonated iclaprim molecule and a mesylate anion. The pyrimidine and chromene units of the iclaprim molecule form an orthogonal arrangement [interplanar angle of 89.67 (6)°], and the 3-nitrogen position of the pyrimidine ring is protonated. Four distinct N—H...O interactions and an additional N—H...N hydrogen bond connect iclaprim and mesylate molecules to one another, resulting in an infinite hydrogen-bonded molecular tape structure. The central section of the tape is formed by a sequence of fused hydrogen-bonded rings involving four distinct ring types.http://scripts.iucr.org/cgi-bin/paper?S2056989022011689crystal structurehydrogen bondingpharmaceuticals |
| spellingShingle | Sandro Neuner Thomas Gelbrich Klaus Wurst Josef Spreitz Sven Nerdinger Ulrich J. Griesser Marijan Stefinovic Herwig Schottenberger Iclaprim mesylate displaying a hydrogen-bonded molecular tape Acta Crystallographica Section E: Crystallographic Communications crystal structure hydrogen bonding pharmaceuticals |
| title | Iclaprim mesylate displaying a hydrogen-bonded molecular tape |
| title_full | Iclaprim mesylate displaying a hydrogen-bonded molecular tape |
| title_fullStr | Iclaprim mesylate displaying a hydrogen-bonded molecular tape |
| title_full_unstemmed | Iclaprim mesylate displaying a hydrogen-bonded molecular tape |
| title_short | Iclaprim mesylate displaying a hydrogen-bonded molecular tape |
| title_sort | iclaprim mesylate displaying a hydrogen bonded molecular tape |
| topic | crystal structure hydrogen bonding pharmaceuticals |
| url | http://scripts.iucr.org/cgi-bin/paper?S2056989022011689 |
| work_keys_str_mv | AT sandroneuner iclaprimmesylatedisplayingahydrogenbondedmoleculartape AT thomasgelbrich iclaprimmesylatedisplayingahydrogenbondedmoleculartape AT klauswurst iclaprimmesylatedisplayingahydrogenbondedmoleculartape AT josefspreitz iclaprimmesylatedisplayingahydrogenbondedmoleculartape AT svennerdinger iclaprimmesylatedisplayingahydrogenbondedmoleculartape AT ulrichjgriesser iclaprimmesylatedisplayingahydrogenbondedmoleculartape AT marijanstefinovic iclaprimmesylatedisplayingahydrogenbondedmoleculartape AT herwigschottenberger iclaprimmesylatedisplayingahydrogenbondedmoleculartape |