A new monoclinic form of the title compound (I), C14H17N3O3S, has been found upon slow crystallization from water. Another monoclinic form of (I) was obtained from a mixture of dichloromethane and diethyl ether [Clerici, Gelmi, Soave & Lo Presti (2002). Tetrahedron 58, 5173-5178]. Both phases crystallize as P21/n with one molecule in the asymmetric unit. The formally single exocyclic C-N bond that connects the -NEt2 moiety with the thiazete ring is considerably shorter than the adjacent, formally double, endocyclic C=N bond. This is likely to be due to the extended conjugated system between the electron-donor diethylammine fragment and the electron-withdrawing sulfonyl group. In the newly discovered polymorph, the methoxy group is rotated by almost 180 deg around the phenyl-OCH3 bond, resulting in a different molecular conformation.

A new monoclinic polymorph of 3-diethylamino-4-(4-methoxyphenyl)-1,1-dioxo-4H-1lambda^6,2-thiazete-4-carbonitrile / A. M. Orlando, L. Lo Presti, R. Soave. - In: ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE. - ISSN 1600-5368. - 66:8(2010 Jul 17), pp. o2032-o2033. [10.1107/S1600536810027558]

A new monoclinic polymorph of 3-diethylamino-4-(4-methoxyphenyl)-1,1-dioxo-4H-1lambda^6,2-thiazete-4-carbonitrile

L. Lo Presti
Secondo
;
R. Soave
Ultimo
2010

Abstract

A new monoclinic form of the title compound (I), C14H17N3O3S, has been found upon slow crystallization from water. Another monoclinic form of (I) was obtained from a mixture of dichloromethane and diethyl ether [Clerici, Gelmi, Soave & Lo Presti (2002). Tetrahedron 58, 5173-5178]. Both phases crystallize as P21/n with one molecule in the asymmetric unit. The formally single exocyclic C-N bond that connects the -NEt2 moiety with the thiazete ring is considerably shorter than the adjacent, formally double, endocyclic C=N bond. This is likely to be due to the extended conjugated system between the electron-donor diethylammine fragment and the electron-withdrawing sulfonyl group. In the newly discovered polymorph, the methoxy group is rotated by almost 180 deg around the phenyl-OCH3 bond, resulting in a different molecular conformation.
Conformational polymorphism ; single crystal X-ray diffraction
Settore CHIM/02 - Chimica Fisica
17-lug-2010
Article (author)
File in questo prodotto:
Non ci sono file associati a questo prodotto.
Pubblicazioni consigliate

I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.

Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/2434/146346
Citazioni
  • ???jsp.display-item.citation.pmc??? ND
  • Scopus 3
  • ???jsp.display-item.citation.isi??? 3
social impact