Crystal structure and Hirshfeld surface analysis of a new di-thio-glycoluril: 1,4-bis-(4-meth-oxy-phen-yl)-3 a-methyl-tetra-hydro-imidazo[4,5- d]imidazole-2,5(1 H,3 H)-di-thione

Jonnie N Asegbeloyin; Kenechukwu J Ifeanyieze; Obinna C Okpareke; Ebube E Oyeka; Tatiana V Groutso

doi:10.1107/S2056989019010764

Crystal structure and Hirshfeld surface analysis of a new di-thio-glycoluril: 1,4-bis-(4-meth-oxy-phen-yl)-3 a-methyl-tetra-hydro-imidazo[4,5- d]imidazole-2,5(1 H,3 H)-di-thione

Acta Crystallogr E Crystallogr Commun. 2019 Aug 6;75(Pt 9):1297-1300. doi: 10.1107/S2056989019010764. eCollection 2019 Sep 1.

Authors

Jonnie N Asegbeloyin¹, Kenechukwu J Ifeanyieze¹, Obinna C Okpareke¹, Ebube E Oyeka¹, Tatiana V Groutso²

Affiliations

¹ Department of Pure and Industrial Chemistry, University of Nigeria, Nsukka 410001, Enugu State, Nigeria.
² School of Chemical Sciences, the University of Auckland Private Bag 92019, Auckland 1142, New Zealand.

Abstract

In the title di-thio-glycoluril derivative, C₁₉H₂₀N₄O₃S₂, there is a difference in the torsion angles between the thio-imidazole moiety and the meth-oxy-phenyl groups on either side of the mol-ecule [C-N-C_ar-C_ar = 116.9 (2) and -86.1 (3)°, respectively]. The N-C-N bond angle on one side of the di-thio-glycoluril 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 mol-ecules 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 inter-actions, leading to the formation of a three-dimensional supra-molecular network. Hirshfeld surface analysis and two-dimensional fingerprint plots were used to investigate the mol-ecular inter-actions in the crystal.

Keywords: C—H⋯π interactions; N—H⋯S hydrogen bonding; cinnamoyl chloride; crystal structure; imidazole; isothiocyanate; thioglycoluril.