(E)-4-Bromo-N-(2,4-dimethoxybenzylidene)aniline

The title Schiff base compound, C15H14BrNO2, adopts an E configuration with respect to the C=N bond. The C and O atoms of the two methoxy substituents lie very close to the dimethoxyphenyl ring plane [maximum deviation = 0.17 (1) Å]. The dihedral angle between the two aromatic rings is 43.69 (16)°, while the plane through the central C—C=N—C system is inclined at 10.6 (6)° to the dimethoxyphenyl ring and 34.6 (3)° to the bromophenyl ring. In the crystal structure, each molecule is involved in the formation of two inversion-related dimers through weak C—H⋯N and C—H⋯O interactions, respectively. These contacts link the molecules into independent rows parallel to the b axis.

The title Schiff base compound, C 15 H 14 BrNO 2 , adopts an E configuration with respect to the C N bond. The C and O atoms of the two methoxy substituents lie very close to the dimethoxyphenyl ring plane [maximum deviation = 0.17 (1) Å ]. The dihedral angle between the two aromatic rings is 43.69 (16) , while the plane through the central C-C N-C system is inclined at 10.6 (6) to the dimethoxyphenyl ring and 34.6 (3) to the bromophenyl ring. In the crystal structure, each molecule is involved in the formation of two inversion-related dimers through weak C-HÁ Á ÁN and C-HÁ Á ÁO interactions, respectively. These contacts link the molecules into independent rows parallel to the b axis.

Comment
As a continuation of our work on the synthesis and structural characterization of Schiff-base compounds (Khalaji et al., 2007;Khalaji & Harrison, 2008;Khalaji & Simpson, 2009), we report here the structure of the title compound, C 15 H 14 BrNO 2 , The compound adopts an E configuration with respect to the C1=N1 bond. The C4, O1 and C7 O2 methoxy substituents lie close to the plane of the C2···C9 ring (maximum deviation 0.17 (1) Å for C7. Bond lengths in the molecule are normal (Allen, et al., 1987) and similar to those found in related compounds (Khalaji et al., 2007;Khalaji & Harrison, 2008;Khalaji & Simpson 2009). The dihedral angle between the two aromatic rings is 43.69 (16) ° while the plane through the central C2-C2?N1-C10 system is inclined at 10.6 (6)° to the dimethoxyphenyl ring and 34.6 (3)° to the bromobenzene ring.
In the crystal structure, each molecule is involved in the formation of two inversion related dimers with R 2 2 (18) and R 2 2 (14) ring motifs (Bernstein et al. 1995) through weak C7-H7A···N1 and C4-H4···O2 interactions respectively, Table  1. These contacts link the molecules into independent rows parallel to the b axis, Fig. 2.

Experimental
To a solution of 2,4-Dimethoxy benzaldehyde (332 mg, 0.2 mmol) in methanol (5 ml), cooled in an ice bath, a solution of 4-bromoaniline (344 mg, 0.2 mmol) in methanol (5 ml) was added slowly dropwise with constant stirring (1 h) at 298 k in the presence of molecular sieves. The mixture was filtered and the solution cooled to 273 K to give the compound in about 85% yield. Pale yellow crystals were grown from methanol.

Refinement
H-atoms were refined using a riding model with d(C-H) = 0.95 Å, U iso = 1.2U eq (C) for aromatic and 0.98 Å, U iso = 1.5U eq (C) for CH 3 H atoms. Fig. 1. The structure of (I) with displacement ellipsoids for the non-hydrogen atoms drawn at the 50% probability level.