Diethyl 1-benzyl-2,2-dioxo-4-phenyl-3,4,6,7,8,8a-hexahydro-1H-pyrrolo[2,1-c][1,4]thiazine-1,3-dicarboxylate

Abstract

Key indicators: single-crystal X-ray study; T = 293 K; mean (C-C) = 0.003 Å; disorder in main residue; R factor = 0.040; wR factor = 0.112; data-to-parameter ratio = 13.3.In the title compound, C 26 H 31 NO 6 S, the five-membered pyrrolidine ring adopts an envelope conformation and the six-membered thiazine ring is in a distorted chair conformation. The crystal packing is stabilized through an intermolecular C-HÁ Á ÁO interaction, generating inversion-related R 2 2 (10) ring motifs.

Isomorphous diethyl 1-(4-chlorobenzyl)-4-(4-chlorophenyl)-2,2-dioxo-3,4,6,7,8,8a-hexahydro-1H-pyrrolo[2,1-c][1,4]thiazine-1,3-dicarboxylate and its 1-(4-methylbenzyl)-4-(4-methylphenyl)-substituted analogue obeying the chloro–methyl exchange rule

“…A search in the Cambridge Structural Database (CSD Version 5.39, update November 2017; Groom et al, 2016) for the skeleton of the title compound without chlorine or methyl substitution for which 3D coordinates were determined with no disorder, no ions and no other errors, with R factors less than 0.05 revealed only one structure, with refcode EXIYAM (Chitradevi, et al, 2011). A search on 4-thiomorpholine-1,1dione gave five hits with refcodes EXIYAM, IDOGIT (Chitradevi et al, 2013), IJULAB (Sugumar et al, 2011), NEVCUN (Indumathi et al,2007) and ZEXYEG (Krishnaiah et al, 1995).…”