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)°.

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Published in Acta Crystallographica Section E Structure Reports Online, v. 70, no. 10, p. o1092-o1093.

Copyright © Penthala et al. 2014

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

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

Related Content

CCDC reference: 1021449

Additional supporting information: crystallographic information; 3D view; checkCIF report

e-70-o1092-sup1.cif (1186 kB)
Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536814019333/sj5404sup1.cif

e-70-o1092-Isup2.hkl (293 kB)
Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814019333/sj5404Isup2.hkl

e-70-o1092-fig1.tif (1719 kB)
A view of the mol­ecule with displacement ellipsoids drawn at the 50% probability level. DOI: 10.1107/S1600536814019333/sj5404fig1.tif

fig(1).pptx (751 kB)
Fig. 1: A view of the mol­ecule with displacement ellipsoids drawn at the 50% probability level.

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