Ethyl (4-benzyl­oxyphen­yl)-6-methyl-2-sulfanyl­­idene-1,2,3,4-tetra­hydro­pyrimidine-5-carboxyl­ate and a redetermination of ethyl (4RS)-4-(4-meth­­oxy­phen­yl)-6-methyl-2-sulfanyl­­idene-1,2,3,4-tetra­hydro­pyrimidine-5-carboxyl­ate, as its 0.105-hydrate, both at 200 K: subtly different hydrogen-bonded ribbons

Sarojini, B. K. and Yathirajan, H. S. and Hosten, Eric C. and Betz, Richard and Glidewell, Christopher (2015) Ethyl (4-benzyl­oxyphen­yl)-6-methyl-2-sulfanyl­­idene-1,2,3,4-tetra­hydro­pyrimidine-5-carboxyl­ate and a redetermination of ethyl (4RS)-4-(4-meth­­oxy­phen­yl)-6-methyl-2-sulfanyl­­idene-1,2,3,4-tetra­hydro­pyrimidine-5-carboxyl­ate, as its 0.105-hydrate, both at 200 K: subtly different hydrogen-bonded ribbons. Acta Crystallographica Section C, 71 (1). pp. 59-64. ISSN 2053-2296

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Official URL: https://doi.org/10.1107/S2053229614026758

Abstract

Two sulfanyl­idene-1,2,3,4-tetra­hydro­pyrimidine derivatives have been synthesized using acid-catalysed cyclo­condensation reactions between thio­urea, ethyl 3-oxo­butano­ate and substituted benzaldehydes. In each of ethyl (4RS)-4-(4-benzyl­oxy­phen­yl)-6-methyl-2-sulfanyl­idene-1,2,3,4-tetra­hydro­py­rimi­dine-5-carboxyl­ate, C21H22N2O3S, (I), where Z′ = 2, and ethyl (4RS)-4-(4-meth­oxy­phen­yl)-6-methyl-2-sulfanyl­idene-1,2,3,4-tetra­hy­dro­pyrimidine-5-carboxyl­ate 0.105-hydrate, C15H18N2O3S·0.105H2O, (II), the reduced pyrimidine ring adopts a con­formation inter­mediate between the boat, screw-boat and twist-boat forms. In (I) and (II), a combination of N—H⋯O and N—H⋯S hydrogen bonds links the organic mol­ecules into ribbons containing alternating R22(8) and R44(20) rings. In (I), the ribbon contains three types of ring, viz. two different R22(8) rings which are both centrosymmetric and R44(20) rings which are not centrosymmetric. In (II), the ribbon contains two types of ring, both of which are centrosymmetric. In compound (II), the ribbons enclose continuous channels which run along the twofold rotation axes in the space group C2/c, and the partial-occupancy water mol­ecules lie within these channels. Structural comparisons are made with a number of related compounds.

Item Type: Article
Uncontrolled Keywords: racemic 1,2,3,4-tetrahydropyrimidine-5-carboxylate esters, cyclocondensation reaction, N-H...O and N-H...S hydrogen bonding, crystal structure, multicomponent reactions
Subjects: C Chemical Science > Chemistry
Divisions: Department of > Chemistry
Depositing User: MUL SWAPNA user
Date Deposited: 02 Nov 2019 09:56
Last Modified: 02 Nov 2019 09:56
URI: http://eprints.uni-mysore.ac.in/id/eprint/9777

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