Polar crystal of vanillylformamide through replacement of the alkene by an isosteric formamide group
Vanillylformamide [systematic name: N-(4-hydroxy-3-methoxybenzyl)formamide], C9H11NO3, (II), has been synthesized from vanillylamine hydrochloride and studied by single-crystal X-ray diffraction. Compound (II) and the well known biologically active eugenol compound (I) can be considered to be `isost...
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International Union of Crystallography
2018-12-01
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| Series: | IUCrData |
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| Online Access: | http://scripts.iucr.org/cgi-bin/paper?S2414314618016309 |
| _version_ | 1818534404718329856 |
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| author | Pierre Baillargeon Tarik Rahem Carl Amigo Daniel Fortin Yves L. Dory |
| author_facet | Pierre Baillargeon Tarik Rahem Carl Amigo Daniel Fortin Yves L. Dory |
| author_sort | Pierre Baillargeon |
| collection | DOAJ |
| description | Vanillylformamide [systematic name: N-(4-hydroxy-3-methoxybenzyl)formamide], C9H11NO3, (II), has been synthesized from vanillylamine hydrochloride and studied by single-crystal X-ray diffraction. Compound (II) and the well known biologically active eugenol compound (I) can be considered to be `isosteres' of each other, since they share comparable molecular shape and volume. The product (II) crystallizes in the space group P1. In the crystal, the vanillylformamide molecules are linked mainly by N—H...O, O—H...O and Csp2—H...O hydrogen bonds, forming infinite two-dimensional polar sheets. These two-dimensional layers pack in a parallel fashion, constructing a polar three-dimensional network. Except for van der Waals forces and weak Csp3—H...O hydrogen bonds, there are no significant intermolecular interactions between the layers. A Cambridge Structural Database search revealed that vanillylamide-related crystals are scarce. |
| first_indexed | 2024-12-11T18:11:12Z |
| format | Article |
| id | doaj.art-ea6113bb4ea640178d8eca52c95b3e6b |
| institution | Directory Open Access Journal |
| issn | 2414-3146 |
| language | English |
| last_indexed | 2024-12-11T18:11:12Z |
| publishDate | 2018-12-01 |
| publisher | International Union of Crystallography |
| record_format | Article |
| series | IUCrData |
| spelling | doaj.art-ea6113bb4ea640178d8eca52c95b3e6b2022-12-22T00:55:35ZengInternational Union of CrystallographyIUCrData2414-31462018-12-01312x18163010.1107/S2414314618016309fy2132Polar crystal of vanillylformamide through replacement of the alkene by an isosteric formamide groupPierre Baillargeon0Tarik Rahem1Carl Amigo2Daniel Fortin3Yves L. Dory4Département de Chimie, Cégep de Sherbrooke, 475 Rue du Cégep, Sherbrooke, Québec, J1E 4K1, CanadaDépartement de Chimie, Cégep de Sherbrooke, 475 Rue du Cégep, Sherbrooke, Québec, J1E 4K1, CanadaDépartement de Chimie, Cégep de Sherbrooke, 475 Rue du Cégep, Sherbrooke, Québec, J1E 4K1, CanadaLaboratoire d'Analyses Structurales par Diffraction des rayons-X, Département de Chimie, Université de Sherbrooke, 2500, Boulevard de l'Université, Sherbrooke, Québec, J1K 2R1, CanadaLaboratoire de Synthèse Supramoléculaire, Département de Chimie, Institut de Pharmacologie, Université de Sherbrooke, 3001 12e Avenue Nord, Sherbrooke, Québec, J1H 5N4, CanadaVanillylformamide [systematic name: N-(4-hydroxy-3-methoxybenzyl)formamide], C9H11NO3, (II), has been synthesized from vanillylamine hydrochloride and studied by single-crystal X-ray diffraction. Compound (II) and the well known biologically active eugenol compound (I) can be considered to be `isosteres' of each other, since they share comparable molecular shape and volume. The product (II) crystallizes in the space group P1. In the crystal, the vanillylformamide molecules are linked mainly by N—H...O, O—H...O and Csp2—H...O hydrogen bonds, forming infinite two-dimensional polar sheets. These two-dimensional layers pack in a parallel fashion, constructing a polar three-dimensional network. Except for van der Waals forces and weak Csp3—H...O hydrogen bonds, there are no significant intermolecular interactions between the layers. A Cambridge Structural Database search revealed that vanillylamide-related crystals are scarce.http://scripts.iucr.org/cgi-bin/paper?S2414314618016309polar crystal structurevanillylamineeugenolcapsaicin analogsisosteres |
| spellingShingle | Pierre Baillargeon Tarik Rahem Carl Amigo Daniel Fortin Yves L. Dory Polar crystal of vanillylformamide through replacement of the alkene by an isosteric formamide group IUCrData polar crystal structure vanillylamine eugenol capsaicin analogs isosteres |
| title | Polar crystal of vanillylformamide through replacement of the alkene by an isosteric formamide group |
| title_full | Polar crystal of vanillylformamide through replacement of the alkene by an isosteric formamide group |
| title_fullStr | Polar crystal of vanillylformamide through replacement of the alkene by an isosteric formamide group |
| title_full_unstemmed | Polar crystal of vanillylformamide through replacement of the alkene by an isosteric formamide group |
| title_short | Polar crystal of vanillylformamide through replacement of the alkene by an isosteric formamide group |
| title_sort | polar crystal of vanillylformamide through replacement of the alkene by an isosteric formamide group |
| topic | polar crystal structure vanillylamine eugenol capsaicin analogs isosteres |
| url | http://scripts.iucr.org/cgi-bin/paper?S2414314618016309 |
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