Crystal structure of 3-(propan-2-yl)-1,3-oxazolidine-2-thione, C6H11NOS

Abstract

C 6 H 11 NOS, orthorhombic, P2 1 2 1 2 1 (no. 19), a =6.0291(6) Å, b =10.615(1) Å, c =11.806(1) Å, V =755.6 Å 3 , Z =4, R gt (F) =0.0244, wR ref (F 2 ) =0.0645, T =100 K. Source of materialSodium N-isopropyl-N-hydroxyethyldithiocarbamate (1 g, 5mmol) was stirred in ethanol (50 ml) and a50% sodium hydroxide solution (1 ml) was added at which point the solution turned clear. The solution was refluxed at 353 Kfor 1h.After cooling to room temperature, the solution was filtered and the sameportion of chloroform added. The mixture was homogenised by shaking. The colourless crystals formedafterthe mother liquor had almost completely evaporated. M.p:340 K. Experimental detailsTheC -bound Ha toms were geometrically placed (C-H =0 .98 1.00 Å) and refined as riding with U iso (H) =1.2-1.5U eq (C). The absolute structure was detemined based on 705 Friedel opposites included in the data set [10]. DiscussionFunctionalised dithiocarbamate ligands such as those containing hydroxyethyl groups, being capable of hydrogen bonding, offer opportunities in crystal engineering [1][2][3][4]. During the course of recent studies [4], it was noted that decomposition/cyclisation of -S 2 CN(iPr)CH 2 CH 2 OH occurred during the synthesis of metal complexes. Subsequently, it was possible to prove this reaction wasb ase-mediated as outlined in "Sourceo fM aterial".T he oxazolidine ring is close to planar with the deviations from the least-squares plane being -0.0582(11), 0.0563(13), 0.0012 (14), 0.0930 (17) and -0.0923(16) Åfor the O1, N1 and C1-C3 atoms, respectively.T he angles aboutthe C1 atom arenon-symmetrical ranging from 110.96(12)°for N1-C1-O1 to 128.70(11)°for N1-C1-S1, reflecting the influence of thel arger thione-S (C1=S1 =1.6680(15) Å) atom. The sum of the angles about the N1 atom is 359.8°confirming its sp 2 character. The molecular structure is stabilised by an intramolecular C4-H4×××S1 interaction. There are no specific intermoleculari nteractions of note. The most closely related structure in the literature is that of 3-(3-chlorophenyl)-4,5-dimethyl-4-oxazoline-2-thione which features aformalC=C double bond within the ring [5].