N′-[(E)-4-(Dimethylamino)benzylidene]-2-(5-methoxy-2-methyl-1H-indol-3-yl)acetohydrazide

In the title compound, C21H24N4O2, inversion-related molecules are linked into dimers through pairs of N—H⋯O hydrogen bonds, which generate R 2 2(8) motifs. As well as dimer formation, an additional N—H⋯O hydrogen bond and two C—H⋯π contacts, involving H atoms from the phenyl ring and the pyrrole and benzene rings of the indole system, generate a three-dimensional network.

In the title compound, C 21 H 24 N 4 O 2 , inversion-related molecules are linked into dimers through pairs of N-HÁ Á ÁO hydrogen bonds, which generate R 2 2 (8) motifs. As well as dimer formation, an additional N-HÁ Á ÁO hydrogen bond and two C-HÁ Á Á contacts, involving H atoms from the phenyl ring and the pyrrole and benzene rings of the indole system, generate a three-dimensional network.   Table 1 Hydrogen-bond geometry (Å , ).

Abdelhamid Comment
Indole-3-acetic acid (IAA) is the main auxin in plants, controlling many important physiological processes including cell enlargement and division, tissue differentiation, and responses to light and gravity (Shahab et al., 2009). In addition, derivatives of substituted indole-acetic acid are active oxidative pro-drugs with potential of cancer therapy (Rossiter et al., 2002). Indomethacin is an example of IAA derivatives exhibits anti-inflammatory, analgesic, and antipyretic properties and is therefore used to treat acute and chronic pain (Klassen, 2001;Kirnura & Doi, 1998). As part of our interest in production of potential pharmaceutical active compounds based on well known pharmacophores e.g indomethacin, we are herein reporting the synthesis and crystal structure of the title compound.

Figure 1
View of the title compound with the atom numbering scheme. Displacement ellipsoids for non-H atoms are drawn at the 50% probability level.

Figure 2
View of the molecular packing and the dimers formed through N-H···O hydrogen bonds of viewed along the b axis.
Hydrogen atoms not involved in hydrogen bonding have been omitted for clarity. where P = (F o 2 + 2F c 2 )/3 (Δ/σ) max < 0.001 Δρ max = 0.21 e Å −3 Δρ min = −0.27 e Å −3 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.