4-(p-Tolylamino)benzaldehyde

In the title compound, C14H13NO, the dihedral angle between the aromatic rings is 66.08 (9)°. Chains are formed along the b axis through intermolecular N—H⋯O hydrogen bonds. The crystal structure is further stabilized by C—H⋯π interactions.

The title compound, C 14 H 13 NO, consists of benzaldehyde and tolyl groups connected through a central amino nitrogen atom (Fig. 1). The dihedral angle between the aromatic rings is 66.08 (9)°. In the crystal, one-dimensional chains are formed along the b-axis through intermolecular N-H···O hydrogen bonding interactions (Fig. 2). The chains are in turn linked through weak intermolecular C-H···π contacts involving the C8-C13 phenyl ring (centroid Cg1) into a three-dimensional network structure (Table 1).

Experimental
To a magnetically stirred solution of p-toluidine (1.0 mmol) and Cs 2 CO 3 (3.2 mmol) in dry DMF cooled by an ice bath were added chloroacetyl chloride (1.2 mmol) and 4-hydroxybenzaldehyde (1.0 mmol). The reaction mixture was then stirred for 30 min at room temperature and placed into a microwave oven (600 W, 424 K) and irradiated for 35 min. The solvent was removed under vacuum and water (20 ml) was added to the residue. The mixture was then extracted with ethyl acetate (4 × 30 ml). The combined organic layers were dried over anhydrous MgSO 4 and evaporated under vacuum to give the crude product. The product was purified by column chromatography on silica gel using ethyl acetate/petroleum ether (yield 89%).

Refinement
In the absence of significant anomalous dispersion effects, Friedel pairs were merged.
Aromatic and methyl H atoms were positioned geometrically and refined using a riding model, with C-H = 0.93 Å for aryl and 0.96 Å for methyl H atoms, and with U iso (H) =1.2U eq (C) for aryl Hatoms, and 1.5U eq (C) for methyl H atoms.
The aldehyde (C14) and N-bound H-atoms were located in a difference Fourier map and their positions and U iso values were freely refined.
supplementary materials sup-2 Figures Fig. 1. The molecular structure of the title compound, with displacement ellipsoids drawn at the 30% probability level.