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.

Crystal structure, Hirshfeld surface and computational study of 1-(9,10-dioxo-9,10-dihydroanthracen-1-yl)-3-propanoylthiourea

“…The versatility of acyl thioureas stems from their ease of preparation and ability to introduce different functionalities, resulting in compounds with very interesting biological properties including antifungal (del Campo et al, 2002Campo et al, , 2004, antitumor Herna ´ndez et al, 2005), antiviral, antibacterial, herbicidal, insecticidal and pharmacological activities (Binzet et al, 2006;Saeed et al, 2010). Recently, our research group reported the synthesis and crystal structures of a number of thiourea derivatives (Asegbeloyin et al, 2018(Asegbeloyin et al, , 2019Okpareke et al, 2020;Oyeka et al, 2021). In a continuation of our series on thiourea derivatives, we present herein the crystal structure, Hirshfeld surface and computational study of a new potential biologically active thiourea derivative with an aminoanthraquinone moiety.…”