N′-[(E)-(Furan-2-yl)methylidene]-2-[4-(2-methylpropyl)phenyl]propanohydrazide

In the title molecule, C18H22N2O2, the furan and benzene rings form a dihedral angle of 70.17 (14)°. In the crystal, strong N—H⋯O and weak C—H⋯O hydrogen bonds link the molecules into chains running parallel to [010].

In the title molecule, C 18 H 22 N 2 O 2 , the furan and benzene rings form a dihedral angle of 70.17 (14) . In the crystal, strong N-HÁ Á ÁO and weak C-HÁ Á ÁO hydrogen bonds link the molecules into chains running parallel to [010].

Related literature
For the synthesis of compounds of similar structure to Ibuprofen undertaken as part of our ongoing study incorporating non-steroidal anti-inflammatory drugs (NSAIDs) as a substructure in the synthesis of potential bio-active pharmacophors, see: Mohamed et al. (2012Mohamed et al. ( , 2013.   Table 1 Hydrogen-bond geometry (Å , ). Manchester Metropolitan University, Tulane University and Erciyes University are gratefully acknowledged for supporting this study. The support of NSF-MRI grant No. 1228232 for the purchase of the diffractometer is gratefully acknowledged.
Supporting information for this paper is available from the IUCr electronic archives (Reference: HG5385).

Comment
Ibuprofen, as other common anti-inflammatory drugs (NSAIDs) which are widely employed in the treatment of pain and inflammation, has been reported to be associated with a number of undesirable effects which, in particular, include gastrointestinal (GI) toxicity (Neeraj et al., 2010;Agrawal et al., 2010;Champion et al., 1997). These studies confirmed that gastrointestinal side-effects of Iburofen and other aroylpropanoic acids are due to the presence of a free carboxylic group in the parent drug (Asif, 2009). Therefore, temporary masking or manipulation of the acidic group in NSAID's are promising means to reduce or to abolish the GI toxicity due to the local action mechanism (Parmeshwari et al., 2009;Alert 1958;Bundgaard, 1991). In view of such facts and following to our ongoing study incorporating NSAID's as a substructure in the synthesis of potential bio-active pharmacophors (Mohamed et al., 2012(Mohamed et al., , 2013 we report the crystal structure of the title compound (I).  (Table 1) connecting the molecules into chains running parallel to the b axis.

Experimental
The title compound was prepared according to our reported method (Mohamed et al., 2012). Clear orange crystals suitable for X-ray analysis were grown from an ethanol solution of (I). M.p. 426-428 K.

Refinement
The H atoms of N2 was located from a difference Fourier map and refined freely. The other H atoms were placed in geometrically idealized positions and refined using a riding model approximation with U iso (H) = 1.2 or 1.5U eq (C).   View of the hydrogen bonding and packing of the title compound down the a axis.

Special details
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 e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles Refinement. Refinement on F 2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F 2 > σ(F 2 ) is used only for calculating -R-factor-obs 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 O1 0.99800 (14