Crystal Structure of the 13-(E)-(2-aminobenzylidene)-parthenolide

Authors

• Shobanbabu Bommagani, University of Arkansas for Medical Sciences
• Narsihma R. Penthala, University of Arkansas for Medical Sciences
• Sean Parkin, University of KentuckyFollow
• Peter A. Crooks, University of Arkansas for Medical Sciences

Abstract

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.

Document Type

Article

Publication Date

11-2018

Notes/Citation Information

Published in Acta Crystallographica Section E: Crystallographic Communications, v. 74, part 11, p. 1543-1546.

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, 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/S2056989018013622

Funding Information

This work was supported by NIH/NCI grant CA158275. SP thanks the National Science Foundation (NSF) MRI program for grants CHE0319176 and CHE1625732.

Related Content

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

checkCIF report

3D view of crystallographic information

Repository Citation

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.
https://uknowledge.uky.edu/chemistry_facpub/143