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Crystal structure of 13-( E )-(2-amino-benzyl-idene)parthenolide.
The title compound, C21 H25 NO3 [systematic name: (1a R ,4 E ,7a S ,8 E ,10a S ,10b R )-8-(2-amino-benzyl-idene)-1a,5-dimethyl-2,3,6,7,7a,8,10a,10b-octa-hydro-oxireno[2',3':9,10]cyclo-deca-[1,2- b ]furan-9(1a H )-one], was synthesized by the reaction of parthenolide [systematic name (1a R ,7a S ,10a S ,10b S , E )-1a,5-dimethyl-8-methyl-ene-2,3,6,7,7a,8,10 a ,10b-octa-hydro-oxireno[2',3':9,10]cyclo-deca-[1,2- b ]furan-9(1a H )-one] with 2-iodo-aniline via Heck reaction conditions. The mol-ecule 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-amino-benzyl-idene 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-amino-benzyl-idine 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 inter-actions.
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