Crystal structure and Hirshfield surface analysis of 4-phenyl-3-(thio-phen-3-ylmeth-yl)-1 H-1,2,4-triazole-5(4 H)-thione

Trung Vu Quoc; Linh Nguyen Ngoc; Dai Do Ba; Thang Pham Chien; Hung Nguyen Huy; Luc Van Meervelt

doi:10.1107/S2056989018007193

Crystal structure and Hirshfield surface analysis of 4-phenyl-3-(thio-phen-3-ylmeth-yl)-1 H-1,2,4-triazole-5(4 H)-thione

Acta Crystallogr E Crystallogr Commun. 2018 May 18;74(Pt 6):812-815. doi: 10.1107/S2056989018007193. eCollection 2018 Jun 1.

Authors

Trung Vu Quoc¹, Linh Nguyen Ngoc¹, Dai Do Ba¹, Thang Pham Chien², Hung Nguyen Huy², Luc Van Meervelt³

Affiliations

¹ Faculty of Chemistry, Hanoi National University of Education, 136 Xuan Thuy, Cau Giay, Hanoi, Vietnam.
² Department of Chemistry, Hanoi University of Science, 19 Le Thanh Tong Street, Ha Ba Discrict, Hanoi, Vietnam.
³ Department of Chemistry, KU Leuven, Biomolecular Architecture, Celestijnenlaan 200F, Leuven (Heverlee), B-3001, Belgium.

Abstract

In the title compound, C₁₃H₁₁N₃S₂, the phenyl ring is twisted from the 1,2,4-triazole plane by 63.35 (9)° and by 47.35 (9)° from the thio-phene plane. In the crystal, chains of mol-ecules running along the c-axis direction are formed by N-H⋯S inter-actions [graph-set motif C(4)]. The 1,2,4-triazole and phenyl rings are involved in π-π stacking inter-actions [centroid-centroid distance = 3.4553 (10) Å]. The thio-phene ring is involved in C-H⋯S and C-H⋯π inter-actions. The inter-molecular inter-actions in the crystal packing were further analysed using Hirshfield surface analysis, which indicates that the most significant contacts are H⋯H (35.8%), followed by S⋯H/H⋯S (26.7%) and C⋯H/H⋯C (18.2%).

Keywords: 1,2,4-triazole; Hirshfield surfaces; crystal structure; thione tautomer; thiophene.

Grants and funding

This work was funded by VLIR-UOS grant ZEIN2014Z182 to L. Van Meervelt.