Crystal structure and Hirshfeld surface analysis of a new dithioglycoluril: 1,4-bis(4-methoxyphenyl)-3a-methyltetrahydroimidazo[4,5-d]imidazole-2,5(1H,3H)-dithione

Abstract

In the title dithioglycoluril derivative, C19H20N4O3S2, there is a difference in the torsion angles between the thioimidazole moiety and the methoxyphenyl groups on either side of the molecule [C—N—Car—Car = 116.9 (2) and −86.1 (3)°, respectively]. The N—C—N bond angle on one side of the dithioglycoluril moiety is slightly smaller compared to that on the opposite side, [110.9 (2)° cf. 112.0 (2)°], probably as a result of the steric effect of the methyl group. In the crystal, N—H...S hydrogen bonds link adjacent molecules to form chains propagating along the c-axis direction. The chains are linked by C—H...S hydrogen bonds, forming layers parallel to the bc plane. The layers are then linked by C—H...π interactions, leading to the formation of a three-dimensional supramolecular network. Hirshfeld surface analysis and two-dimensional fingerprint plots were used to investigate the molecular interactions in the crystal.

Keywords

• crystal structure
• thioglycoluril
• imidazole
• cinnamoyl chloride
• isothiocyanate
• N—H...S hydrogen bonding
• C—H...π interactions