(2S,3R,4S,4aR)-2,3,4,7-Tetrahydroxy-3,4,4a,5-tetrahydro[1,3]dioxolo[4,5-j] phenanthridin-6(2H)-one hemihydrate
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JUCOV, Evgheni, KORNIENKO, Alexander, MASI, Marco, EVIDENTE, Antonio, ANTIPIN, Mikhail. (2S,3R,4S,4aR)-2,3,4,7-Tetrahydroxy-3,4,4a,5-tetrahydro[1,3]dioxolo[4,5-j] phenanthridin-6(2H)-one hemihydrate. In: Acta Crystallographica Section E: Structure Reports Online, 2013, vol. 69, pp. o9-o10. ISSN 1600-5368. DOI: https://doi.org/10.1107/S1600536812048763
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Acta Crystallographica Section E: Structure Reports Online
Volumul 69 / 2013 / ISSN 1600-5368

(2S,3R,4S,4aR)-2,3,4,7-Tetrahydroxy-3,4,4a,5-tetrahydro[1,3]dioxolo[4,5-j] phenanthridin-6(2H)-one hemihydrate

DOI:https://doi.org/10.1107/S1600536812048763

Pag. o9-o10

Jucov Evgheni1, Kornienko Alexander2, Masi Marco3, Evidente Antonio3, Antipin Mikhail4
 
1 Institute of Applied Physics, Academy of Sciences of Moldova,
2 Texas State University, San Marcos,
3 University of Naples Federico II,
4 New Mexico Highlands University, Las Vegas
 
 
Disponibil în IBN: 22 februarie 2024


Rezumat

The title natural compound, isolated from Narcissus pseudonarcissus var. King Alfred crystallizes as a hemihydrate, C14H13NO7·0.5H2O, with four crystallographically independent dioxolophenanthridinone molecules and two crystallographically independent solvent water molecules in the asymmetric unit. All four crystallographically independent dioxolophenanthridinone molecules are geometrically very similar and differ only in the orientations of the three hydroxy groups at the terminal cyclohexene rings. The five-membered dioxolane ring has a planar conformation (the r.m.s. deviations are 0.010, 0.019, 0.025 and 0.004 Å, for the four crystallographically independent molecules), and the six-membered dihydropyridone and cyclohexene rings adopt sofa conformations in each molecule. The flattened structure of each dioxolophenanthridinone molecule is supported by a strong intramolecular O - H⋯O hydrogen bond. The N atom has a slightly pyramidalized configuration. In the crystal, the dioxolophenanthridinone molecules form layers parallel to (101) with O - H⋯O and N - H⋯O hydrogen bonds linking the dioxolophenanthridinone molecules both within and between the layers and the water molecules, forming a three-dimensional framework. The absolute configurations of the chiral centers are 2S, 3R, 4S and 4aR.

Cuvinte-cheie
Narcissus, Narcissus pseudonarcissus