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. 2013 Sep 7;69(Pt 10):o1522-3.
doi: 10.1107/S1600536813024203. eCollection 2013.

2-{(E)-[(2Z)-2-(1,2-Di-hydro-phthalazin-1-yl-idene)hydrazinyl-idene]meth-yl}phenol

M K Prasanna  1 , M Sithambaresan, K Pradeepkumar, M R Prathapachandra Kurup
Affiliations

2-{(E)-[(2Z)-2-(1,2-Di-hydro-phthalazin-1-yl-idene)hydrazinyl-idene]meth-yl}phenol

M K Prasanna et al. Acta Crystallogr Sect E Struct Rep Online. .

Abstract

The title compound, C15H12N4O, adopts an E conformation with respect to the azomethine bond and crystallizes in its hydrazinyl-idene tautomeric form. The dihedral angle between the ring systems is 15.98 (7)°. The phenol O-H group forms an intra-molecular O-H⋯N hydrogen bond. In the crystal, pairs of N-H⋯N and C-H⋯O hydrogen bonds link neighbouring mol-ecules into centrosymmetric dimers. These dimers are inter-connected by means of three types of π-π stacking inter-actions. One, with a centroid-centroid distance of 3.577 (1) Å [inter-planar separation = 3.4673 (6) Å], connects adjacent mol-ecules into centrosymmetric dimers. The other two inter-actions, on the outward facing sides of the dimers, are between phenol rings of neighboring mol-ecules [centroid-centroid separation = 3.7907 (13) Å and inter-planar separation = 3.5071 (8) Å], and between phthalazin units [centroid-centroid separation = 3.6001 (12) Å and inter-planar separation = 3.4891 (7) Å]. In combination, the π-π inter-actions lead to the formation of infinite layers with mol-ecules 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 supra-molecular architecture.

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Figures

Fig. 1.
Fig. 1.
ORTEP view of the compound, drawn with 50% probability displacement ellipsoids for the non-H atoms (the minor moiety H atom was omitted for clarity).
Fig. 2.
Fig. 2.
Graphical representation showing the centrosymmetric dimers by means of hydrogen bonding in the crystal structure of C15H12N4O. The minor disordered H atoms were omitted for clarity.
Fig. 3.
Fig. 3.
Graphical representation showing π–π interactions between whole molecules into centrosymmetric dimers in the crystal structure of the title compound.
Fig. 4.
Fig. 4.
Graphical representation showing π–π interactions between phenol and pthalazin rings in the crystal structure of the title compound.
Fig. 5.
Fig. 5.
Graphical representation showing π–π interactions that lead to formation of infinite layers in the crystal structure of the title compound.
Fig. 6.
Fig. 6.
Graphical representation showing neighboring layers formed by π–π interactions and connected through intermolecular N–H···N and C–H···O H-bonds
Fig. 7.
Fig. 7.
Packing diagram showing the molecular assembly of the title compound along the a axis.
See this image and copyright information in PMC

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