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

---

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 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-HO 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-HO(nitro) and furanyl-C-HO(nitro) inter­actions, as well as – 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(thien­yl), have been investigated by Hirshfeld surface analysis, which confirms the dominance of the conventional N-HO hydrogen bonding to the overall mol­ecular packing.

---

Keywords: crystal structure; carbohydrazide; hydrogen bonding; conformation; Hirshfeld surface analysis. Document Type: Research Article DOI: https://doi.org/10.1107/S2056989016009968 Publication date: 1 de Janeiro de 2016 [:en]

---

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 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-HO 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-HO(nitro) and furanyl-C-HO(nitro) inter­actions, as well as – 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(thien­yl), have been investigated by Hirshfeld surface analysis, which confirms the dominance of the conventional N-HO hydrogen bonding to the overall mol­ecular packing.

---

Keywords: crystal structure; carbohydrazide; hydrogen bonding; conformation; Hirshfeld surface analysis. Document Type: Research Article DOI: https://doi.org/10.1107/S2056989016009968 Publication date: 1 de Janeiro de 2016 [:]