The title compound, C21H25NO3 [systematic name: (1aR,4E,7aS,8E,10aS,10bR)-8-(2-aminobenzylidene)-1a,5-dimethyl-2,3,6,7,7a,8,10a,10b-octahydrooxireno[2′,3′:9,10]cyclodeca[1,2-b]furan-9(1aH)-one], was synthesized by the reaction of parthenolide [systematic name (1aR,7aS,10aS,10bS,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] with 2-iodoaniline via Heck reaction conditions. The molecule is composed of fused ten-, five- (lactone), and three-membered (epoxide) rings. The lactone ring shows a flattened envelope-type conformation (r.m.s. deviation from planarity = 0.0477 Å), and bears a 2-aminobenzylidene substituent that is disordered over two conformations [occupancy factors 0.901 (4) and 0.099 (4)]. The ten-membered ring has an approximate chair–chair conformation. The dihedral angle between the 2-aminobenzylidine moiety (major component) and the lactone ring (mean plane) is 59.93 (7)°. There are no conventional hydrogen bonds, but there are a number of weaker C—H⋯O-type interactions.
Digital Object Identifier (DOI)
This work was supported by NIH/NCI grant CA158275. SP thanks the National Science Foundation (NSF) MRI program for grants CHE0319176 and CHE1625732.
Supporting information: this article has supporting information at journals.iucr.org/e.
Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S2056989018013622/sj5564sup1.cif
Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989018013622/sj5564Isup2.hkl
CCDC reference: 1869537
3D view of crystallographic information
Bommagani, Shobanbabu; Penthala, Narsihma R.; Parkin, Sean; and Crooks, Peter A., "Crystal Structure of the 13-(E)-(2-aminobenzylidene)-parthenolide" (2018). Chemistry Faculty Publications. 143.