Crystal structure and identification of resonance forms of diethyl 2-(3-oxoiso-1,3-dihydrobenzofuran-1-ylidene)malonate
The reaction of diethyl malonate with phthaloyl chloride in acetonitrile in the presence of triethylamine and magnesium chloride results in the formation of the title compound, diethyl 2-(3-oxo-1,3-dihydro-2-benzofuran-1-ylidene)propanedioate, C15H14O6. One of the ester groups of the diethyl malonat...
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| Format: | Article |
| Language: | English |
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International Union of Crystallography
2017-10-01
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| Series: | Acta Crystallographica Section E: Crystallographic Communications |
| Subjects: | |
| Online Access: | http://scripts.iucr.org/cgi-bin/paper?S2056989017013962 |
| _version_ | 1818959457894268928 |
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| author | Mikhail S. Tyumentsev Mark R. StJ. Foreman Britt-Marie Steenari Alexandra M. Z. Slawin |
| author_facet | Mikhail S. Tyumentsev Mark R. StJ. Foreman Britt-Marie Steenari Alexandra M. Z. Slawin |
| author_sort | Mikhail S. Tyumentsev |
| collection | DOAJ |
| description | The reaction of diethyl malonate with phthaloyl chloride in acetonitrile in the presence of triethylamine and magnesium chloride results in the formation of the title compound, diethyl 2-(3-oxo-1,3-dihydro-2-benzofuran-1-ylidene)propanedioate, C15H14O6. One of the ester groups of the diethyl malonate fragment is almost coplanar with the isobenzofuran unit, while the plane of the other group is perpendicular to it [dihedral angles = 5.45 (3) and 83.30 (3)°, respectively]. The C—C and C—O distances both in the heterocyclic furan ring and the diethyl malonate fragment are indicative of the dipolar delocalization occurring within the isobenzofuran unit. This delocalization is likely to be responsible for the unusual intermolecular O...O contact [2.756 (2) Å], established between the O atom of the furan ring and the carbonyl O atom of the diethyl malonate fragment. In the crystal, weak C—H...O interactions are observed, which link the molecules into [100] chains. |
| first_indexed | 2024-12-20T11:41:57Z |
| format | Article |
| id | doaj.art-b041b2022b334624b5fc2993b145c495 |
| institution | Directory Open Access Journal |
| issn | 2056-9890 |
| language | English |
| last_indexed | 2024-12-20T11:41:57Z |
| publishDate | 2017-10-01 |
| publisher | International Union of Crystallography |
| record_format | Article |
| series | Acta Crystallographica Section E: Crystallographic Communications |
| spelling | doaj.art-b041b2022b334624b5fc2993b145c4952022-12-21T19:41:59ZengInternational Union of CrystallographyActa Crystallographica Section E: Crystallographic Communications2056-98902017-10-0173101576157910.1107/S2056989017013962hb7700Crystal structure and identification of resonance forms of diethyl 2-(3-oxoiso-1,3-dihydrobenzofuran-1-ylidene)malonateMikhail S. Tyumentsev0Mark R. StJ. Foreman1Britt-Marie Steenari2Alexandra M. Z. Slawin3Nuclear Chemistry and Industrial Materials Recycling, Department of Chemistry and Chemical Engineering, Chalmers University of Technology, Gothenburg, Sweden, SE 41296Nuclear Chemistry and Industrial Materials Recycling, Department of Chemistry and Chemical Engineering, Chalmers University of Technology, Gothenburg, Sweden, SE 41296Nuclear Chemistry and Industrial Materials Recycling, Department of Chemistry and Chemical Engineering, Chalmers University of Technology, Gothenburg, Sweden, SE 41296School of Chemistry, University of St. Andrews, Purdie Building, North Haugh, St. Andrews, Fife, Scotland, KY16 9STThe reaction of diethyl malonate with phthaloyl chloride in acetonitrile in the presence of triethylamine and magnesium chloride results in the formation of the title compound, diethyl 2-(3-oxo-1,3-dihydro-2-benzofuran-1-ylidene)propanedioate, C15H14O6. One of the ester groups of the diethyl malonate fragment is almost coplanar with the isobenzofuran unit, while the plane of the other group is perpendicular to it [dihedral angles = 5.45 (3) and 83.30 (3)°, respectively]. The C—C and C—O distances both in the heterocyclic furan ring and the diethyl malonate fragment are indicative of the dipolar delocalization occurring within the isobenzofuran unit. This delocalization is likely to be responsible for the unusual intermolecular O...O contact [2.756 (2) Å], established between the O atom of the furan ring and the carbonyl O atom of the diethyl malonate fragment. In the crystal, weak C—H...O interactions are observed, which link the molecules into [100] chains.http://scripts.iucr.org/cgi-bin/paper?S2056989017013962crystal structure3-alkylidene-3H-isobenzofuran-1-onesdelocalizationenolate |
| spellingShingle | Mikhail S. Tyumentsev Mark R. StJ. Foreman Britt-Marie Steenari Alexandra M. Z. Slawin Crystal structure and identification of resonance forms of diethyl 2-(3-oxoiso-1,3-dihydrobenzofuran-1-ylidene)malonate Acta Crystallographica Section E: Crystallographic Communications crystal structure 3-alkylidene-3H-isobenzofuran-1-ones delocalization enolate |
| title | Crystal structure and identification of resonance forms of diethyl 2-(3-oxoiso-1,3-dihydrobenzofuran-1-ylidene)malonate |
| title_full | Crystal structure and identification of resonance forms of diethyl 2-(3-oxoiso-1,3-dihydrobenzofuran-1-ylidene)malonate |
| title_fullStr | Crystal structure and identification of resonance forms of diethyl 2-(3-oxoiso-1,3-dihydrobenzofuran-1-ylidene)malonate |
| title_full_unstemmed | Crystal structure and identification of resonance forms of diethyl 2-(3-oxoiso-1,3-dihydrobenzofuran-1-ylidene)malonate |
| title_short | Crystal structure and identification of resonance forms of diethyl 2-(3-oxoiso-1,3-dihydrobenzofuran-1-ylidene)malonate |
| title_sort | crystal structure and identification of resonance forms of diethyl 2 3 oxoiso 1 3 dihydrobenzofuran 1 ylidene malonate |
| topic | crystal structure 3-alkylidene-3H-isobenzofuran-1-ones delocalization enolate |
| url | http://scripts.iucr.org/cgi-bin/paper?S2056989017013962 |
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