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AuthorHijji, Yousef
AuthorBenjamin, Ellis
AuthorJasinski, Jerry P.
AuthorButcher, Ray J.
Available date2024-02-27T09:29:52Z
Publication Date2018-01-01
Publication NameActa Crystallographica Section E: Crystallographic Communications
Identifierhttp://dx.doi.org/10.1107/S2056989018014317
CitationHijji, Y., Benjamin, E., Jasinski, J. P., & Butcher, R. J. (2018). Crystal structure of the thalidomide analog (3aR*, 7aS*)-2-(2, 6-dioxopiperidin-3-yl) hexahydro-1H-isoindole-1, 3 (2H)-dione. Acta Crystallographica Section E: Crystallographic Communications, 74(11), 1595-1598.‏
URIhttps://www.scopus.com/inward/record.uri?partnerID=HzOxMe3b&scp=85056533155&origin=inward
URIhttp://hdl.handle.net/10576/52294
AbstractThe title compound, C13H16N2O4, crystallizes in the monoclinic centrosymmetric space group, P21/c, with four molecules in the asymmetric unit, thus there is no crystallographically imposed symmetry and it is a racemic mixture. The structure consists of a six-membered unsaturated ring bound to a five-membered pyrrolidine-2,5-dione ring N-bound to a six-membered piperidine-2,6-dione ring and thus has the same basic skeleton as thalidomide, except for the six-membered unsaturated ring substituted for the aromatic ring. In the crystal, the molecules are linked into inversion dimers by R22(8) hydrogen bonding involving the N - H group. In addition, there are bifurcated C - H⋯O interactions involving one of the O atoms on the pyrrolidine-2,5-dione with graph-set notation R12(5). These interactions along with C - H⋯O interactions involving one of the O atoms on the piperidine-2,6-dione ring link the molecules into a complex three-dimensional array. There is pseudomerohedral twinning present which results from a 180° rotation about the [100] reciprocal lattice direction and with a twin law of 1 0 0 0 1 0 0 0 1[BASF 0.044 (1)].
SponsorThis report was made possible by a NPRP award [NPRP-7-495-1-094] from Qatar National Research Fund (a member of The Qatar Foundation). The statements made herein are solely the responsibility of the authors. RJB is grateful for the
Languageen
PublisherInternational Union of Crystallography
SubjectCrystal structure
pseudomerohedral twinning
thalidomide analogs
TitleCrystal structure of the thalidomide analog (3aR∗,7aS∗)-2-(2,6-dioxopiperidin-3-yl)hexahydro-1H-isoindole-1,3(2H)-dione
TypeArticle
Pagination1595-1598
Volume Number74
dc.accessType Open Access


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