Acta Cryst. (2014). C70, 416-420 [ doi:10.1107/S2053229614006111 ]
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-HO and N-HS hydrogen bonds creates a molecular strap with C(6) and R22(8) motifs, which is further stabilized by an SS 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-HO soft hydrogen bonds and the other, with an R22(8) motif, is produced via a pair of N-HO hard hydrogen bonds. In the packing of (3), molecules A and B form two different types of one-dimensional chain by intermolecular C-HN hydrogen bonds, and by CN and OS contacts, respectively. Two such kinds of chain are connected alternately via interchain C-HO hydrogen bonds, giving a two-dimensional sheet. Finally, a three-dimensional supramolecular structure is formed through weak intersheet C-HF 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.
Structure factor file (CIF format) (40.4 kbytes)
Structure factor file (CIF format) (119.0 kbytes)
Structure factor file (CIF format) (243.1 kbytes)
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