N′-[(1E)-(5-Nitrofuran-2-yl)methylidene]thiophene-2-carbohydrazide: crystal structure and Hirshfeld surface analysis

• Main Authors: Laura N. F. Cardoso, Thais C. M. Nogueira, James L. Wardell, Solange M. S. V. Wardell, Marcus V. N. de Souza, Mukesh M. Jotani, Edward R. T. Tiekink
• Format: Article
• Language: English
• Published: International Union of Crystallography 2016-07-01
• Series: Acta Crystallographica Section E: Crystallographic Communications
• Subjects: crystal structure; carbohydrazide; hydrogen bonding; conformation; Hirshfeld surface analysis
• Online Access: http://scripts.iucr.org/cgi-bin/paper?S2056989016009968

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 molecule. 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 supramolecular 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) interactions, as well as π–π interactions between the thienyl and furanyl rings [inter-centroid distance = 3.515 (2) Å]. These, and other, weak intermolecular interactions, e.g. nitro-N—O...π(thienyl), have been investigated by Hirshfeld surface analysis, which confirms the dominance of the conventional N—H...O hydrogen bonding to the overall molecular packing.