N′-Benzoyl-3-hydroxy-2-naphthohydrazide

In the title compound, C18H14N2O3, the dihedral angle between the planes of the naphthalene and phenyl ring systems is 2.64 (2)°. Molecules are engaged in π–π stacking (mean interplanar distance = 3.339 between naphthalene rings and 3.357 Å between benzene rings )and hydrogen-bonding interactions.

In the title compound, C 18 H 14 N 2 O 3 , the dihedral angle between the planes of the naphthalene and phenyl ring systems is 2.64 (2) . Molecules are engaged instacking (mean interplanar distance = 3.339 between naphthalene rings and 3.357 Å between benzene rings )and hydrogen-bonding interactions.
The molecular structure of (I), C 18 H 14 N 2 O 3 , is illustrated in Fig.1. The bond length and bond angles in (I)are within normal ranges. The dihedral angle between the planes of naphthalene and benzene rings is 2.640 (2)°. Atom O2 is only approximately co-planar with the naphthalene plane and deviates from the benzene plane by 0.788 (2)Å. The maximum atomic deviation (O3) from the naphthalene plane is 1.403 (2)Å.
The mean interplanar distance of 3.339Å between naphthalene rings and 3.357Å between benzene rings suggests that the ligands are engaged in π-π stacking interactions (Fig. 2). The crystal structure of (I) is stabilized by O-H···O and N-H···O hydrogen bonding (Table 1).

Experimental
Acetic anhydride (6.8 g, 66.8 mmol) and 3-hydroxy-2-naphthalenecarbohydrazide (11.3 g, 56.0 mmol) were added to 120 ml of chloroform with an external ice-water bath. The reaction mixture was slowly warmed to room temperature and stirred for 8 h. After leaving overnight in a refrigerator, the resulting white precipitate was filtered and rinsed with chloroform and Refinement. Refinement of F 2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F 2 , conventional R-factors R are based on F, with F set to zero for negative F 2 . The threshold expression of F 2 > σ(F 2 ) is used only for calculating Rfactors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F 2 are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å 2 )
x y z U iso */U eq C1 0.8504 (7