Acta Crystallographica Section C

Structural Chemistry

Volume 70, Part 4 (April 2014)


organic compounds



sf3223 scheme

Acta Cryst. (2014). C70, 416-420    [ doi:10.1107/S2053229614006111 ]

Supra­molecular structures in three thio­uracil derivatives: 5,6-tri­methyl­ene-2-sulfan­yl­idene-1,2-di­hydro­pyrimidin-4(3H)-one, 2-(4-fluorobenzyl­sulfan­yl)-5,6-tri­methyl­ene­pyrimidin-4(3H)-one and methyl 2-{[2-(4-fluoro­benzyl­sulfan­yl)-5,6-tri­methyl­ene­pyrimidin-4-yl]­oxy}acetate

Y.-J. Zhou, J. Lv, K. Yu, J.-P. Ma and D.-S. Guo

Abstract: The mol­ecules of the title compounds, C7H8N2OS, (1), C14H13FN2OS, (2), and C17H17FN2O3S, (3), crystallize in the space groups C2/m, C2/c and Ia, respectively. Compounds (1) and (2), an S-alkyl­ated derivative of (1), consist of only one symmetry-independent mol­ecule, while (3), an O-alkyl­ated derivative of (2), contains two independent mol­ecules in the asymmetric unit. The molecules of (1) sit on crystallographic mirror planes. In the supra­molecular structure of (1), a combination of N-H...O and N-H...S hydrogen bonds creates a mol­ecular strap with C(6) and R22(8) motifs, which is further stabilized by an S...S contact. In the packing of (2), a one-dimensional mol­ecular column is made up of two kinds of dimers. One dimer, with an R22(18) motif, is formed by a pair of C-H...O soft hydrogen bonds and the other, with an R22(8) motif, is produced via a pair of N-H...O hard hydrogen bonds. In the packing of (3), mol­ecules A and B form two different types of one-dimensional chain by inter­molecular C-H...N hydrogen bonds, and by C...N and O...S contacts, respectively. Two such kinds of chain are connected alternately via inter­chain C-H...O hydrogen bonds, giving a two-dimensional sheet. Finally, a three-dimensional supra­molecular structure is formed through weak intersheet C-H...F hydrogen bonds. The study of the mol­ecular and supra­molecular structures of thio­uracil derivatives is significant in the development of lipoprotein-associated phospho­lipase A2 inhibitors.

CCDC references: 992569, 992570 and 992571

Formula: C7H8N2OS, C14H13FN2OS and C17H17FN2O3S

Keywords: crystal structure; 5,6-tri­methyl­enepyrimidin-4-one; thio­uracil derivatives; hydrogen bonding; supra­molecular structure.


hkldisplay filedownload file

Structure factor file (CIF format) (40.4 kbytes)
[ doi:10.1107/S2053229614006111/sf32231sup2.hkl ]
Contains datablock 1


hkldisplay filedownload file

Structure factor file (CIF format) (119.0 kbytes)
[ doi:10.1107/S2053229614006111/sf32232sup3.hkl ]
Contains datablock 2


hkldisplay filedownload file

Structure factor file (CIF format) (243.1 kbytes)
[ doi:10.1107/S2053229614006111/sf32233sup4.hkl ]
Contains datablock 3


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