Acta Crystallographica Section E

Structure Reports Online

Volume 69, Part 10 (October 2013)

organic compounds

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


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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