(Z)-3α-(1,3-Dioxoisoindolin-2-yl)-17(20)-pregnene

Yue Qi,Hong-Quan Duan,Nan Qin

doi:10.1107/s1600536811027632

Yue Qi, Hong-Quan Duan + Show 1 more

Open Access

https://doi.org/10.1107/s1600536811027632

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Abstract

The title compound, C29H37NO2, crystallized with two independent molecules in an asymmetric unit in which the conformation of the cyclohexyl ring of the pregnene moiety bonded to the 3α-(1,3-dioxoisoindolin-2-yl)- ring system differs: in one molecule it is in a chair conformation, while in the other it exhibits a half-chair conformation. The other six-membered rings in the pregnene moiety are in chair conformations and the five-membered rings are in envelope forms in both molecules. In both molecules, the 3α-(1,3-dioxoisoindolin-2-yl)- ring systems are individually approximately planar, with r.m.s. devtaions 0.0148 and 0.0264 Å. The structure is consolidated by intermolecular C—H⋯O hydrogen-bonding interactions involving the carbonyl O atoms and methyl, methylene and methylidyne groups, resulting in a two-dimensional structure.

Highlights

The title compound, C29H37NO2, crystallized with two independent molecules in an asymmetric unit in which the conformation of the cyclohexyl ring of the pregnene moiety bonded to the 3-(1,3-dioxoisoindolin-2-yl)- ring system differs: in one molecule it is in a chair conformation, while in the other it exhibits a half-chair conformation
The other six-membered rings in the pregnene moiety are in chair conformations and the five-membered rings are in envelope forms in both molecules
The title compound was synthesized from epiandrosterone, a pregnane alkaloid isolated from Pachysandra axillaris, a traditional chinese medicine

Summary

Data collection

The title compound, C29H37NO2, crystallized with two independent molecules in an asymmetric unit in which the conformation of the cyclohexyl ring of the pregnene moiety bonded to the 3-(1,3-dioxoisoindolin-2-yl)- ring system differs: in one molecule it is in a chair conformation, while in the other it exhibits a half-chair conformation. The other six-membered rings in the pregnene moiety are in chair conformations and the five-membered rings are in envelope forms in both molecules. In both molecules, the 3-(1,3dioxoisoindolin-2-yl)- ring systems are individually approximately planar, with r.m.s. devtaions 0.0148 and 0.0264 Å. The structure is consolidated by intermolecular C—H O hydrogen-bonding interactions involving the carbonyl O atoms and methyl, methylene and methylidyne groups, resulting in a two-dimensional structure

Related literature

This work was supported by the National Natural Science

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