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) Full article
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Acta Crystallographica Section E
, E-ISSN: 2056-9890 |
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Output data | Year: 2016, Volume: 72, Number: 10, Pages: 1429-1433 Pages count : 5 DOI: 10.1107/s2056989016014420 | ||||||||
Tags | azaheterocycles; crystal structure; epimerization; intramolecular Diels-Alder furan (IMDAF) reaction; tautomerism | ||||||||
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Abstract:
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].
Cite:
Poplevin D.S.
, Zubkov F.I.
, Dorovatovskii P.V.
, Zubavichus Y.V.
, Khrustalev V.N.
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. 2016. V.72. N10. P.1429-1433. DOI: 10.1107/s2056989016014420 WOS Scopus
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. 2016. V.72. N10. P.1429-1433. DOI: 10.1107/s2056989016014420 WOS Scopus
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Full text from publisher
Dates:
Submitted: | Aug 12, 2016 |
Accepted: | Sep 11, 2016 |
Published online: | Sep 16, 2016 |
Published print: | Oct 1, 2016 |
Identifiers:
Web of science | WOS:000385460500018 |
Scopus | 2-s2.0-84990866786 |
Chemical Abstracts | 2016:1620378 |
Chemical Abstracts (print) | 168:272026 |
OpenAlex | W2519972361 |