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Acta Cryst. (2013). E69, o1522-o1523
[ doi:10.1107/S1600536813024203 ]

2-{(E)-[(2Z)-2-(1,2-Dihydrophthalazin-1-ylidene)hydrazinylidene]methyl}phenol

M. K. Prasanna, M. Sithambaresan, K. Pradeepkumar and M. R. P. Kurup

Abstract: The title compound, C15H12N4O, adopts an E conformation with respect to the azomethine bond and crystallizes in its hydrazinylidene tautomeric form. The dihedral angle between the ring systems is 15.98 (7)°. The phenol O-H group forms an intramolecular O-H...N hydrogen bond. In the crystal, pairs of N-H...N and C-H...O hydrogen bonds link neighbouring molecules into centrosymmetric dimers. These dimers are interconnected by means of three types of [pi]-[pi] stacking interactions. One, with a centroid-centroid distance of 3.577 (1) Å [interplanar separation = 3.4673 (6) Å], connects adjacent molecules into centrosymmetric dimers. The other two interactions, on the outward facing sides of the dimers, are between phenol rings of neighboring molecules [centroid-centroid separation = 3.7907 (13) Å and interplanar separation = 3.5071 (8) Å], and between phthalazin units [centroid-centroid separation = 3.6001 (12) Å and interplanar separation = 3.4891 (7) Å]. In combination, the [pi]-[pi] interactions lead to the formation of infinite layers with molecules stacked along [0-11]. These layers are, in turn, connected with neighbouring layers through the N-H...N and C-H...O hydrogen bonds, yielding a three-dimensional supramolecular architecture.


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