Crystal structures of the two epimers from the unusual thermal C6-epimerization of 5-oxo-1,2,3,5,5a,6,7,9b-octahydro-7,9a-epoxypyrrolo[2,1-a]isoindole-6-carboxylic acid, 5a(RS),6(SR),7(RS),9a(SR),9b(SR) and 5a(RS),6(RS),7(RS),9a(SR),9b(SR)
The isomeric title compounds, C12H13NO4 (Ia) and C12H13NO4 (IIa), the products of an usual thermal C6-epimerization of 5-oxo-1,2,3,5,5a,6,7,9b-octahydro-7,9a-epoxypyrrolo[2,1-a]isoindole-6-carboxylic acid, represent the two different diastereomers and have very similar molecular geometries. The mole...
| Main Authors: | , , , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
International Union of Crystallography
2016-10-01
|
| Series: | Acta Crystallographica Section E: Crystallographic Communications |
| Subjects: | |
| Online Access: | http://scripts.iucr.org/cgi-bin/paper?S2056989016014420 |
| _version_ | 1818322009016238080 |
|---|---|
| author | Dmitry S. Poplevin Fedor I. Zubkov Pavel V. Dorovatovskii Yan V. Zubavichus Victor N. Khrustalev |
| author_facet | Dmitry S. Poplevin Fedor I. Zubkov Pavel V. Dorovatovskii Yan V. Zubavichus Victor N. Khrustalev |
| author_sort | Dmitry S. Poplevin |
| collection | DOAJ |
| description | The isomeric title compounds, C12H13NO4 (Ia) and C12H13NO4 (IIa), the products of an usual thermal C6-epimerization of 5-oxo-1,2,3,5,5a,6,7,9b-octahydro-7,9a-epoxypyrrolo[2,1-a]isoindole-6-carboxylic acid, represent the two different diastereomers and have very similar molecular geometries. The molecules of both compounds comprise a fused tetracyclic system containing four five-membered rings (pyrrolidine, pyrrolidinone, dihydrofuran and tetrahydrofuran), all of which adopt the usual envelope conformations. The dihedral angle between the basal planes of the pyrrolidine and pyrrolidinone rings are 14.3 (2) and 16.50 (11)°, respectively, for (Ia) and (IIa). The nitrogen atom has a slightly pyramidalized geometry [bond-angle sum = 355.9 and 355.3°, for (Ia) and (IIa)], respectively. In the crystal of (Ia), molecules form zigzag-like hydrogen-bonded chains along [010] through strong O—H...O hydrogen bonds and are further linked by weak C—H...O hydrogen bonds into complex two-tier layers parallel to (100). Unlike (Ia), the crystal of (IIa) contains centrosymmetric cyclic hydrogen-bonded dimers [graph set R22(14)], formed through strong O—H...O hydrogen bonds and are further linked by weak C—H...O hydrogen bonds into ribbons extending across [101]. |
| first_indexed | 2024-12-13T10:49:58Z |
| format | Article |
| id | doaj.art-c405d92e854d495b8cbf9229fad103ac |
| institution | Directory Open Access Journal |
| issn | 2056-9890 |
| language | English |
| last_indexed | 2024-12-13T10:49:58Z |
| publishDate | 2016-10-01 |
| publisher | International Union of Crystallography |
| record_format | Article |
| series | Acta Crystallographica Section E: Crystallographic Communications |
| spelling | doaj.art-c405d92e854d495b8cbf9229fad103ac2022-12-21T23:49:53ZengInternational Union of CrystallographyActa Crystallographica Section E: Crystallographic Communications2056-98902016-10-0172101429143310.1107/S2056989016014420zs2368Crystal structures of the two epimers from the unusual thermal C6-epimerization of 5-oxo-1,2,3,5,5a,6,7,9b-octahydro-7,9a-epoxypyrrolo[2,1-a]isoindole-6-carboxylic acid, 5a(RS),6(SR),7(RS),9a(SR),9b(SR) and 5a(RS),6(RS),7(RS),9a(SR),9b(SR)Dmitry S. Poplevin0Fedor I. Zubkov1Pavel V. Dorovatovskii2Yan V. Zubavichus3Victor N. Khrustalev4Organic Chemistry Department, Peoples' Friendship University of Russia (RUDN University), 6 Miklukho-Maklay St., Moscow 117198, Russian FederationOrganic Chemistry Department, Peoples' Friendship University of Russia (RUDN University), 6 Miklukho-Maklay St., Moscow 117198, Russian FederationNational Research Centre "Kurchatov Institute", 1 Acad. Kurchatov Sq., Moscow 123182, Russian FederationNational Research Centre "Kurchatov Institute", 1 Acad. Kurchatov Sq., Moscow 123182, Russian FederationInorganic Chemistry Department, Peoples' Friendship University of Russia (RUDN University), 6 Miklukho-Maklay St., Moscow 117198, Russian FederationThe isomeric title compounds, C12H13NO4 (Ia) and C12H13NO4 (IIa), the products of an usual thermal C6-epimerization of 5-oxo-1,2,3,5,5a,6,7,9b-octahydro-7,9a-epoxypyrrolo[2,1-a]isoindole-6-carboxylic acid, represent the two different diastereomers and have very similar molecular geometries. The molecules of both compounds comprise a fused tetracyclic system containing four five-membered rings (pyrrolidine, pyrrolidinone, dihydrofuran and tetrahydrofuran), all of which adopt the usual envelope conformations. The dihedral angle between the basal planes of the pyrrolidine and pyrrolidinone rings are 14.3 (2) and 16.50 (11)°, respectively, for (Ia) and (IIa). The nitrogen atom has a slightly pyramidalized geometry [bond-angle sum = 355.9 and 355.3°, for (Ia) and (IIa)], respectively. In the crystal of (Ia), molecules form zigzag-like hydrogen-bonded chains along [010] through strong O—H...O hydrogen bonds and are further linked by weak C—H...O hydrogen bonds into complex two-tier layers parallel to (100). Unlike (Ia), the crystal of (IIa) contains centrosymmetric cyclic hydrogen-bonded dimers [graph set R22(14)], formed through strong O—H...O hydrogen bonds and are further linked by weak C—H...O hydrogen bonds into ribbons extending across [101].http://scripts.iucr.org/cgi-bin/paper?S2056989016014420intramolecular Diels–Alder furan (IMDAF) reactionazaheterocyclesepimerizationtautomerismcrystal structure |
| spellingShingle | Dmitry S. Poplevin Fedor I. Zubkov Pavel V. Dorovatovskii Yan V. Zubavichus Victor N. Khrustalev Crystal structures of the two epimers from the unusual thermal C6-epimerization of 5-oxo-1,2,3,5,5a,6,7,9b-octahydro-7,9a-epoxypyrrolo[2,1-a]isoindole-6-carboxylic acid, 5a(RS),6(SR),7(RS),9a(SR),9b(SR) and 5a(RS),6(RS),7(RS),9a(SR),9b(SR) Acta Crystallographica Section E: Crystallographic Communications intramolecular Diels–Alder furan (IMDAF) reaction azaheterocycles epimerization tautomerism crystal structure |
| title | Crystal structures of the two epimers from the unusual thermal C6-epimerization of 5-oxo-1,2,3,5,5a,6,7,9b-octahydro-7,9a-epoxypyrrolo[2,1-a]isoindole-6-carboxylic acid, 5a(RS),6(SR),7(RS),9a(SR),9b(SR) and 5a(RS),6(RS),7(RS),9a(SR),9b(SR) |
| title_full | Crystal structures of the two epimers from the unusual thermal C6-epimerization of 5-oxo-1,2,3,5,5a,6,7,9b-octahydro-7,9a-epoxypyrrolo[2,1-a]isoindole-6-carboxylic acid, 5a(RS),6(SR),7(RS),9a(SR),9b(SR) and 5a(RS),6(RS),7(RS),9a(SR),9b(SR) |
| title_fullStr | Crystal structures of the two epimers from the unusual thermal C6-epimerization of 5-oxo-1,2,3,5,5a,6,7,9b-octahydro-7,9a-epoxypyrrolo[2,1-a]isoindole-6-carboxylic acid, 5a(RS),6(SR),7(RS),9a(SR),9b(SR) and 5a(RS),6(RS),7(RS),9a(SR),9b(SR) |
| title_full_unstemmed | Crystal structures of the two epimers from the unusual thermal C6-epimerization of 5-oxo-1,2,3,5,5a,6,7,9b-octahydro-7,9a-epoxypyrrolo[2,1-a]isoindole-6-carboxylic acid, 5a(RS),6(SR),7(RS),9a(SR),9b(SR) and 5a(RS),6(RS),7(RS),9a(SR),9b(SR) |
| title_short | Crystal structures of the two epimers from the unusual thermal C6-epimerization of 5-oxo-1,2,3,5,5a,6,7,9b-octahydro-7,9a-epoxypyrrolo[2,1-a]isoindole-6-carboxylic acid, 5a(RS),6(SR),7(RS),9a(SR),9b(SR) and 5a(RS),6(RS),7(RS),9a(SR),9b(SR) |
| title_sort | crystal structures of the two epimers from the unusual thermal c6 epimerization of 5 oxo 1 2 3 5 5a 6 7 9b octahydro 7 9a epoxypyrrolo 2 1 a isoindole 6 carboxylic acid 5a rs 6 sr 7 rs 9a sr 9b sr and 5a rs 6 rs 7 rs 9a sr 9b sr |
| topic | intramolecular Diels–Alder furan (IMDAF) reaction azaheterocycles epimerization tautomerism crystal structure |
| url | http://scripts.iucr.org/cgi-bin/paper?S2056989016014420 |
| work_keys_str_mv | AT dmitryspoplevin crystalstructuresofthetwoepimersfromtheunusualthermalc6epimerizationof5oxo12355a679boctahydro79aepoxypyrrolo21aisoindole6carboxylicacid5ars6sr7rs9asr9bsrand5ars6rs7rs9asr9bsr AT fedorizubkov crystalstructuresofthetwoepimersfromtheunusualthermalc6epimerizationof5oxo12355a679boctahydro79aepoxypyrrolo21aisoindole6carboxylicacid5ars6sr7rs9asr9bsrand5ars6rs7rs9asr9bsr AT pavelvdorovatovskii crystalstructuresofthetwoepimersfromtheunusualthermalc6epimerizationof5oxo12355a679boctahydro79aepoxypyrrolo21aisoindole6carboxylicacid5ars6sr7rs9asr9bsrand5ars6rs7rs9asr9bsr AT yanvzubavichus crystalstructuresofthetwoepimersfromtheunusualthermalc6epimerizationof5oxo12355a679boctahydro79aepoxypyrrolo21aisoindole6carboxylicacid5ars6sr7rs9asr9bsrand5ars6rs7rs9asr9bsr AT victornkhrustalev crystalstructuresofthetwoepimersfromtheunusualthermalc6epimerizationof5oxo12355a679boctahydro79aepoxypyrrolo21aisoindole6carboxylicacid5ars6sr7rs9asr9bsrand5ars6rs7rs9asr9bsr |