N′-(Adamantan-2-ylidene)benzohydrazide

The title molecule, C17H20N2O, is a functionalized hydrazine with benzoyl and adamantyl substituents attached to the two hydrazine N atoms. In the crystal, molecules are linked via N—H⋯N hydrogen bonds, forming chains propagating along the a-axis direction. There are also C—H⋯O, C—H⋯N and C—H⋯π interactions present within the chains.

The title molecule, C 17 H 20 N 2 O, is a functionalized hydrazine with benzoyl and adamantyl substituents attached to the two hydrazine N atoms. In the crystal, molecules are linked via N-HÁ Á ÁN hydrogen bonds, forming chains propagating along the a-axis direction. There are also C-HÁ Á ÁO, C-HÁ Á ÁN and C-HÁ Á Á interactions present within the chains.

N′-(Adamantan-2-ylidene)benzohydrazide
Maha S. Almutairi, Ali A. El-Emam, Nasser R. El-Brollosy, Mohammed Said-Abdelbaky and Santiago García-Granda Comment Derivatives of adamantane have long been known for their diverse biological activities including antiviral activity against the influenza (Togo et al., 1968) and HIV viruses (El-Emam et al., 2004). Moreover, adamantane derivatives were reported to exhibit marked antibacterial and anti-inflammatory activities (Kadi et al., 2007(Kadi et al., , 2010El-Emam & Ibrahim, 1991). In continuation to our interest in the chemical and pharmacological properties of adamantane derivatives (Almutairi et al., 2012;El-Emam et al., 2012), we synthesized the title compound as a precursor for potential chemotherapeutic agents. Herein, we report on the synthesis and crystal structure of the title compound.
The title molecule, Fig. 1, is a functionalized hydrazine with benzoyl and adamantyl substituents attached to the two hydrazine nitrogen atoms, N1 and N2.
In the crystal, molecules are linked via N-H···N hydrogen bonds forming chains propagating along the a axis direction.

Experimental
A mixture of benzohydrazide (1.36 g, 0.01 mol), 2-adamantanone (1.5 g, 0.01 mol), in ethanol (10 ml) was heated under reflux with stirring for 4 h. On cooling, the precipitated crystalline solid was filtered, dried and recrystallized from ethanol to yield 2.52 g (94%) of the title compound as colourless needle crystals [M.p. 517-519 K]. Spectroscopic data for the title compound are given in the archived CIF.

Refinement
The NH H-atom was located in a difference electron-density map and freely refined. The C-bound H-atoms were included in calculated positions and treated as riding atoms: C-H = 0.93, 0.97 and 0.96 Å for CH(aromatic), CH 2 and CH(methine) H-atoms, respectively, with U iso (H) = 1.2U eq (parent C-atom).

N′-(Adamantan-2-ylidene)benzohydrazide
Crystal data Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles 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 R-factors(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.