Crystal structure of rac-cis-N-(2,4-dinitrophenyl)-3,4-diphenyl-5H-1,2-oxathiol- 5-amine 2-oxide, C21H15N3O6S, sultim and sultam structures – part 4

Abstract

C 21H 15N 3 O 6 S,monoclinic, P 121 / c 1(no. 14), a =9.624(3) Å, b =8.446(3) Å, c =23.756(8) Å, b =93.998(7)°, V =1926.3 Å 3 , Z =4, R gt (F) =0.080, Source of materialThe title compound was prepared by oxidation of 2-(2,4-dinitrophenyl)-4,5-diphenylisothiazolium perchlorate with H 2 O 2 in acetic acid at room temperature for 25 minutes (m.p. 419-423 K). Crystals were obtained from acetone. Experimental detailsThe high R values are caused by the poor quality of the crystals which is reflected in asymmetricreflection profiles and confirmed by two further data collections. DiscussionThe oxidation of monocyclic and bicyclic isothiazolium salts has been research intensively since the last years [1][2][3][4][5][6][7] and can be classified in two principle oxidation methods. Atfirst, the salts can be oxidized with H 2 O 2 in acetic acid to yield 3-hydroperoxysultims rac-cis/ trans,s ultams and 3-oxosultams [1][2][3][4][5]. Furthermore, the isothiazolium salts reacted with magnesium monoperoxyphthalate (MMPP)inwater or alcohol to obtain the 3-hydroxysultims rac-cis/ trans,sultams or 3-alkoxysultams [6,7]. The rac-cis-N -(2,4-dinitrophenyl)-3,4-diphenyl-5H -1,2-oxathiol-5-amine 2-oxidew as obtained unexpectedly after oxidation of the isothiazolium salt to 3-hydroxysultim, ring cleavage between the sulfura nd nitrogen atoms, rearrangement and cyclization. The molecular structurei sc haracterized by as trong intramolecular hydrogen bond (N1-H1N···O2). The bond para-