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 200K: subtly different hydrogen-bonded ribbons

B.K. Sarojini, H.S. Yathirajan, E.C. Hosten, R. Betz, C. Glidewell

Research output: Contribution to journalArticlepeer-review

5 Citations (Scopus)

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 R 2 2(8) and R 4 4(20) rings. In (I), the ribbon contains three types of ring, viz. two different R 2 2(8) rings which are both centrosymmetric and R 4 4(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.

Original languageEnglish
Pages (from-to)59-64
Number of pages6
JournalActa Crystallographica Section C Structural Chemistry
Volume71
Issue number1
DOIs
Publication statusPublished - Jan 2015

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

Fingerprint

Dive into the research topics of '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 200K: subtly different hydrogen-bonded ribbons'. Together they form a unique fingerprint.

Cite this