Synthesis, mol-ecular and crystal structure of 1-(1,2-di-hydro-phthalazin-1-yl-idene)-2-[1-(thio-phen-2-yl)ethyl-idene]hydrazine

Acta Crystallographica. Section E, Crystallographic Communications
Felicite Majoumo-MbeIkome Iris Efeti

Abstract

The title compound, C14H12N4S, was synthesized by the condensation reaction of hydralazine and 2-acetyl-thio-phene and during the reaction, a proton transfer from the imino nitro-gen atom to one of the endocylic nitro-gen atoms occurred. The compound crystallizes in the monoclinic crystal system with two independent mol-ecules (mol-ecules 1 and 2) in the asymmetric unit. In each mol-ecule, there is a slight difference in the orientation of the thio-phene ring with respect to phthalazine ring system, mol-ecule 1 showing a dihedral angle of 42.51 (1)° compared to 8.48 (1)° in mol-ecule 2. This implies an r.m.s deviation of 0.428 (1) Å between the two mol-ecules for the 19 non-H atoms. The two independent mol-ecules are connected via two N-H⋯N hydrogen bonds, forming dimers which inter-act by two bifurcated π-π stacking inter-actions to build tetra-meric motifs. The latter are packed in the ac plane via weak C-H⋯π inter-actions and along the b axis via C-H ⋯N and C-H⋯π inter-actions. This results a three-dimensional architecture with a tilted herringbone packing mode.

References

May 8, 2004·The Journal of Pharmacology and Experimental Therapeutics·Lisa M KaminskasPhilip C Burcham
Mar 17, 2006·European Journal of Medicinal Chemistry·Paola ViciniRoberta Loddo
Oct 24, 2007·Spectrochimica Acta. Part A, Molecular and Biomolecular Spectroscopy·Azza A Shoukry, Mohamed M Shoukry
Dec 25, 2007·Acta Crystallographica. Section A, Foundations of Crystallography·George M Sheldrick
Jan 28, 2009·Acta Crystallographica. Section D, Biological Crystallography·Anthony L Spek
Jan 9, 2015·Acta Crystallographica. Section C, Structural Chemistry·George M Sheldrick
Apr 7, 2016·Acta Crystallographica Section B, Structural Science, Crystal Engineering and Materials·Colin R GroomSuzanna C Ward
Nov 21, 2017·Acta Crystallographica. Section E, Crystallographic Communications·Linh Nguyen NgocLuc Van Meervelt

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