Mol-ecular and crystal structure, Hirshfeld analysis and DFT investigation of 5-(furan-2-yl-methyl-idene)thia-zolo[3,4- a]benzimidazole-2-thione

Hafsa Khaldi; Ahmed Djafri; Youcef Megrouss; Nawel Khelloul; Abdelkader Chouaih; Ayada Djafri

doi:10.1107/S2056989020015017

Mol-ecular and crystal structure, Hirshfeld analysis and DFT investigation of 5-(furan-2-yl-methyl-idene)thia-zolo[3,4- a]benzimidazole-2-thione

Acta Crystallogr E Crystallogr Commun. 2020 Nov 13;76(Pt 12):1832-1836. doi: 10.1107/S2056989020015017. eCollection 2020 Dec 1.

Authors

Hafsa Khaldi¹, Ahmed Djafri^{2

3}, Youcef Megrouss³, Nawel Khelloul³, Abdelkader Chouaih³, Ayada Djafri¹

Affiliations

¹ Laboratory of Organic Applied Synthesis (LSOA), Department of Chemistry, Faculty of Sciences, University of Oran 1, Ahmed Ben Bella, 31000 Oran, Algeria.
² Centre de Recherche Scientifique et Technique en Analyses Physico-Chimiques, (CRAPC), BP 384-Bou-Ismail-RP 42004, Tipaza, Algeria.
³ Laboratory of Technology and Solid Properties (LTPS), Abdelhamid Ibn Badis University, BP 227 Mostaganem 27000, Algeria.

Abstract

The thia-zolo[3,4-a]benzimidazole fused-ring system in the title compound, C₁₄H₈N₂OS₂, is nearly planar, the r.m.s. deviation being 0.0073 Å. The thia-zolo-benzimidazole-2-thione system is almost in the same plane as the furan-2-yl-methyl-ene moiety, with a dihedral angle of 5.6 (2)° between the two least-squares planes. In the crystal, adjacent mol-ecules are connected by weak inter-molecular inter-actions (C-H⋯N and slipped π-π stacking) into a three-dimensional network. The nature of the inter-molecular inter-actions was also qu-anti-fied by Hirshfeld surface analysis. DFT analysis indicates a good agreement of the experimentally determined and the theoretically calculated mol-ecular structures.

Keywords: DFT analysis; benzimidazoles; crystal structure; reactivity; thiazoles.

Grants and funding

This work was funded by Ministère de l’Enseignement Supérieur et de la Recherche Scientifique grant . Direction Générale de la Recherche Scientifique et du Développement Technologique grant . ATRST Algeria grant . Abdelhamid Ibn Badis University of Mostaganem grant .