Tetra-n-butylammonium orotate monohydrate: knowledge-based comparison of the results of accurate and lower-resolution analyses and a non-routine disorder refinement
The title hydrated molecular salt (systematic name: tetra-n-butylammonium 2,6-dioxo-1,2,3,6-tetrahydropyrimidine-4-carboxylate monohydrate), C16H36N+·C5H3N2O4−·H2O, crystallizes with N—H...O and O—H...O hydrogen-bonded double-stranded antiparallel ribbons consisting of the hydrophilic orotate monoan...
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| Format: | Article |
| Language: | English |
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International Union of Crystallography
2019-11-01
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| Series: | Acta Crystallographica Section E: Crystallographic Communications |
| Subjects: | |
| Online Access: | http://scripts.iucr.org/cgi-bin/paper?S2056989019013380 |
| _version_ | 1798024449936588800 |
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| author | Irene Ara Zeineb Basdouri Larry R. Falvello Mohsen Graia Pablo Guerra Milagros Tomás |
| author_facet | Irene Ara Zeineb Basdouri Larry R. Falvello Mohsen Graia Pablo Guerra Milagros Tomás |
| author_sort | Irene Ara |
| collection | DOAJ |
| description | The title hydrated molecular salt (systematic name: tetra-n-butylammonium 2,6-dioxo-1,2,3,6-tetrahydropyrimidine-4-carboxylate monohydrate), C16H36N+·C5H3N2O4−·H2O, crystallizes with N—H...O and O—H...O hydrogen-bonded double-stranded antiparallel ribbons consisting of the hydrophilic orotate monoanions and water molecules, separated by the bulky hydrophobic cations. The hydrophobic and hydrophilic regions of the structure are joined by weaker non-classical C—H...O hydrogen bonds. An accurate structure analysis conducted at T = 100 K is compared to a lower-resolution less accurate determination using data measured at T = 295 K. The results of both analyses are evaluated using a knowledge-based approach, and it is found that the less accurate room-temperature structure analysis provides geometric data that are similar to those derived from the accurate low-temperature analysis, with both sets of results consistent with previously analyzed structures. A minor disorder of one methyl group in the cation at low temperature was found to be slightly more complex at room temperature; while still involving a minor fraction of the structure, the disorder at room temperature was found to require a non-routine treatment, which is described in detail. |
| first_indexed | 2024-04-11T18:03:46Z |
| format | Article |
| id | doaj.art-0fb2231bbbe0491eb0f2fd9605394e31 |
| institution | Directory Open Access Journal |
| issn | 2056-9890 |
| language | English |
| last_indexed | 2024-04-11T18:03:46Z |
| publishDate | 2019-11-01 |
| publisher | International Union of Crystallography |
| record_format | Article |
| series | Acta Crystallographica Section E: Crystallographic Communications |
| spelling | doaj.art-0fb2231bbbe0491eb0f2fd9605394e312022-12-22T04:10:23ZengInternational Union of CrystallographyActa Crystallographica Section E: Crystallographic Communications2056-98902019-11-0175111632163710.1107/S2056989019013380hb7858Tetra-n-butylammonium orotate monohydrate: knowledge-based comparison of the results of accurate and lower-resolution analyses and a non-routine disorder refinementIrene Ara0Zeineb Basdouri1Larry R. Falvello2Mohsen Graia3Pablo Guerra4Milagros Tomás5Instituto de Síntesis Quimica y Catálisis Homogénea (ISQCH), C.S.I.C.-University of Zaragoza, Departamento de Química Inorgánica, Pedro Cerbuna 12, E-50009 Zaragoza, SpainLaboratoire de Matériaux, Cristallochimie et Thermodynamique Appliquée, Département de Chimie, Faculté des Sciences de Tunis, Université de Tunis El Manar, 2092 El Manar II, Tunis, TunisiaUniversity of Zaragoza-C.S.I.C., Instituto de Ciencia de Materiales de Aragón (ICMA), Departamento de Química Inorgánica, E-50009 Zaragoza, SpainLaboratoire de Matériaux, Cristallochimie et Thermodynamique Appliquée, Département de Chimie, Faculté des Sciences de Tunis, Université de Tunis El Manar, 2092 El Manar II, Tunis, TunisiaUniversity of Zaragoza-C.S.I.C., Instituto de Ciencia de Materiales de Aragón (ICMA), Departamento de Química Inorgánica, E-50009 Zaragoza, SpainInstituto de Síntesis Quimica y Catálisis Homogénea (ISQCH), C.S.I.C.-University of Zaragoza, Departamento de Química Inorgánica, Pedro Cerbuna 12, E-50009 Zaragoza, SpainThe title hydrated molecular salt (systematic name: tetra-n-butylammonium 2,6-dioxo-1,2,3,6-tetrahydropyrimidine-4-carboxylate monohydrate), C16H36N+·C5H3N2O4−·H2O, crystallizes with N—H...O and O—H...O hydrogen-bonded double-stranded antiparallel ribbons consisting of the hydrophilic orotate monoanions and water molecules, separated by the bulky hydrophobic cations. The hydrophobic and hydrophilic regions of the structure are joined by weaker non-classical C—H...O hydrogen bonds. An accurate structure analysis conducted at T = 100 K is compared to a lower-resolution less accurate determination using data measured at T = 295 K. The results of both analyses are evaluated using a knowledge-based approach, and it is found that the less accurate room-temperature structure analysis provides geometric data that are similar to those derived from the accurate low-temperature analysis, with both sets of results consistent with previously analyzed structures. A minor disorder of one methyl group in the cation at low temperature was found to be slightly more complex at room temperature; while still involving a minor fraction of the structure, the disorder at room temperature was found to require a non-routine treatment, which is described in detail.http://scripts.iucr.org/cgi-bin/paper?S2056989019013380crystal structureorotatehydrophobic–hydrophilic molecular ion pairhirshfeld surface analysisknowledge-based analysismogul geometry check |
| spellingShingle | Irene Ara Zeineb Basdouri Larry R. Falvello Mohsen Graia Pablo Guerra Milagros Tomás Tetra-n-butylammonium orotate monohydrate: knowledge-based comparison of the results of accurate and lower-resolution analyses and a non-routine disorder refinement Acta Crystallographica Section E: Crystallographic Communications crystal structure orotate hydrophobic–hydrophilic molecular ion pair hirshfeld surface analysis knowledge-based analysis mogul geometry check |
| title | Tetra-n-butylammonium orotate monohydrate: knowledge-based comparison of the results of accurate and lower-resolution analyses and a non-routine disorder refinement |
| title_full | Tetra-n-butylammonium orotate monohydrate: knowledge-based comparison of the results of accurate and lower-resolution analyses and a non-routine disorder refinement |
| title_fullStr | Tetra-n-butylammonium orotate monohydrate: knowledge-based comparison of the results of accurate and lower-resolution analyses and a non-routine disorder refinement |
| title_full_unstemmed | Tetra-n-butylammonium orotate monohydrate: knowledge-based comparison of the results of accurate and lower-resolution analyses and a non-routine disorder refinement |
| title_short | Tetra-n-butylammonium orotate monohydrate: knowledge-based comparison of the results of accurate and lower-resolution analyses and a non-routine disorder refinement |
| title_sort | tetra n butylammonium orotate monohydrate knowledge based comparison of the results of accurate and lower resolution analyses and a non routine disorder refinement |
| topic | crystal structure orotate hydrophobic–hydrophilic molecular ion pair hirshfeld surface analysis knowledge-based analysis mogul geometry check |
| url | http://scripts.iucr.org/cgi-bin/paper?S2056989019013380 |
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