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Supramolecular structures in three thiouracil derivatives: 5,6‐trimethylene‐2‐sulfanylidene‐1,2‐dihydropyrimidin‐4(3 H )‐one, 2‐(4‐fluorobenzylsulfanyl)‐5,6‐trimethylenepyrimidin‐4(3 H )‐one and methyl 2‐{[2‐(4‐fluorobenzylsulfanyl)‐5,6‐trimethylenepyrimidin‐4‐yl]oxy}acetate
Author(s) -
Zhou YuJun,
Lv Jing,
Yu Kai,
Ma JianPing,
Guo DianShun
Publication year - 2014
Publication title -
acta crystallographica section c
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.304
H-Index - 17
ISSN - 2053-2296
DOI - 10.1107/s2053229614006111
Subject(s) - hydrogen bond , supramolecular chemistry , crystallography , dimer , molecule , chemistry , intermolecular force , stereochemistry , crystal structure , organic chemistry
The molecules of the title compounds, C 7 H 8 N 2 OS, (1), C 14 H 13 FN 2 OS, (2), and C 17 H 17 FN 2 O 3 S, (3), crystallize in the space groups C 2/ m , C 2/ 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 R 2 2 (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 R 2 2 (18) motif, is formed by a pair of C—H...O soft hydrogen bonds and the other, with an R 2 2 (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 A 2 inhibitors.