N'-[(1E)-(5-Nitro-furan-2-yl)methyl-idene]thio-phene-2-carbohydrazide: crystal structure and Hirshfeld surface analysis

Acta Crystallogr E Crystallogr Commun. 2016 Jun 24;72(Pt 7):1025-31. doi: 10.1107/S2056989016009968. eCollection 2016 Jul 1.

Abstract

In the title carbohydrazide, C10H7N3O4S, the dihedral angle between the terminal five-membered rings is 27.4 (2)°, with these lying to the same side of the plane through the central CN2C(=O) atoms (r.m.s. deviation = 0.0403 Å), leading to a curved mol-ecule. The conformation about the C=N imine bond [1.281 (5) Å] is E, and the carbonyl O and amide H atoms are anti. In the crystal, N-H⋯O hydrogen bonds lead to supra-molecular chains, generated by a 41 screw-axis along the c direction. A three-dimensional architecture is consolidated by thienyl-C-H⋯O(nitro) and furanyl-C-H⋯O(nitro) inter-actions, as well as π-π inter-actions between the thienyl and furanyl rings [inter-centroid distance = 3.515 (2) Å]. These, and other, weak inter-molecular inter-actions, e.g. nitro-N-O⋯π(thien-yl), have been investigated by Hirshfeld surface analysis, which confirms the dominance of the conventional N-H⋯O hydrogen bonding to the overall mol-ecular packing.

Keywords: Hirshfeld surface analysis; carbohydrazide; conformation; crystal structure; hydrogen bonding.