N-Phenyl-2-(propan-2-ylidene)hydrazinecarboxamide

In the title compound, C10H13N3O, the hydrazinecarboxamide N—N—C(=O)—N unit is nearly planar [maximum deviation = 0.018 (2) Å] and is inclined at a dihedral angle of 8.45 (10)° with respect to the plane of the phenyl ring. The molecular structure is stabilized by an intramolecular C—H⋯O hydrogen bond which generates an S(6) ring motif. In the crystal, molecules are linked into an inversion dimer by pairs of N—H⋯O and C—H⋯O hydrogen bonds.

In the title compound, C 10 H 13 N 3 O, the hydrazinecarboxamide N-N-C( O)-N unit is nearly planar [maximum deviation = 0.018 (2) Å ] and is inclined at a dihedral angle of 8.45 (10) with respect to the plane of the phenyl ring. The molecular structure is stabilized by an intramolecular C-HÁ Á ÁO hydrogen bond which generates an S(6) ring motif. In the crystal, molecules are linked into an inversion dimer by pairs of N-HÁ Á ÁO and C-HÁ Á ÁO hydrogen bonds.

Kun Fun Comment
Epilepsy is one of the most widespread pathologies of the human brain, affecting approximately 1% of world population.
Nevertheless, in the case of single drug treatment, the number of non-responding patients is as high as 30% and in chronic medication with currently available antiepileptic drugs (AEDs) may result in severe side-effects and undesired drug interactions (Sander & Shorvon, 1987). That is why, in recent years, intensive research has been carried out aiming at the development of new therapeutic strategies for epilepsy. Arylsemicarbazones have been documented to display significant anticonvulsant activity through the work of Dimmock and his colleagues (Dimmock et al., 1993). Arylsemicarbazones are structurally dissimilar from many common monocyclic anticonvulsants which incorporate the dicarboxamide functionality, such as hydantoins and succinimides, which may contribute to toxic side effects. In general, semicarbazones have rapid onsets of action and one of the ways in which these compounds exerted their anticonvulsant activity is likely to be their interaction with the chloride channels.

Figure 1
The molecular structure of the title compound showing 50% probability displacement ellipsoids for non-H atoms.

Figure 2
The crystal structure of the title compound, viewed along the a axis. H atoms not involved in hydrogen bonds (dashed lines) have been omitted for clarity.

N-Phenyl-2-(propan-2-ylidene)hydrazinecarboxamide
Crystal data where P = (F o 2 + 2F c 2 )/3 (Δ/σ) max = 0.002 Δρ max = 0.18 e Å −3 Δρ min = −0.13 e Å −3 Extinction correction: SHELXTL (Sheldrick, 2008), Fc * =kFc[1+0.001xFc 2 λ 3 /sin(2θ)] -1/4 Extinction coefficient: 0.0093 (12) Special details Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. 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 > 2sigma(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.