Abstract

The title compound, C33H35NO6 [systematic name: (Z)-3-(4-{(E)-[(E)-1a,5-dimethyl-9-oxo-2,3,7,7a-tetra­hydro­oxireno[2′,3′:9,10]cyclo­deca­[1,2-b]furan-8(1aH,6H,9H,10aH,10bH)-yl­idene]meth­yl}phen­yl)-2-(3,4,5-tri­meth­oxy­phen­yl)acrylo­ni­trile methanol hemisolvate], C33H35NO6·0.5CH3OH, was prepared by the reaction of (Z)-3-(4-iodo­phen­yl)-2-(3,4,5-tri­meth­oxy­phen­yl)acrylo­nitrile with parthenolide [systematic name: (E)-1a,5-dimethyl-8-methyl­ene-2,3,6,7,7a,8,10a,10b-octa­hy­dro­oxireno[2′,3′:9,10]cyclo­deca­[1,2-b]furan-9(1aH)-one] under Heck reaction conditions. The mol­ecule is built up from fused ten-, five- (lactone) and three-membered (epoxide) rings with a {4-[(Z)-2-cyano-2-(3,4,5-tri­meth­oxy­phen­yl)ethen­yl]phen­yl}methyl­idene group as a substituent. The 4-[(Z)-2-cyano-2-(3,4,5-tri­meth­oxy­phen­yl)ethen­yl]phenyl group on the parthenolide exocyclic double bond is oriented in a trans position to the lactone ring to form the E isomer. The dihedral angle between the benzene ring of the phenyl moiety and the lactone ring mean plane is 21.93 (4)°.

Document Type

Article

Publication Date

10-2014

Notes/Citation Information

Published in Acta Crystallographica Section E: Crystallographic Communications, v. 70, part 10, p. o1092-o1093.

This is an open-access article distributed under the terms of the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

Digital Object Identifier (DOI)

https://doi.org/10.1107/S1600536814019333

Funding Information

This work was supported by NIH/NCI (grant No. CA158275).

Related Content

Supporting information for this paper is available from the IUCr electronic archives (Reference: SJ5404).

CCDC reference: 1021449

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536814019333/sj5404sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536814019333/sj5404Isup2.hkl

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3D view of crystallographic information

sj5404.pptx (218 kB)
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sj5404sup1.cif (1186 kB)
Crystal structure: contains datablocks global, I.

sj5404Isup2.hkl (293 kB)
Structure factors: contains datablock I.

sj5404fig1.html (31 kB)
Supporting figures: Fig. 1.

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