(E)-1-(3-Methoxyphenyl)ethanone 4-nitrophenylhydrazone

Crystals of the title compound, C15H15N3O3, were obtained from a condensation reaction of 4-nitrophenylhydrazine and 3-methoxyacetophenone. In the crystal structure, the methoxyphenyl ring is twisted slightly with respect to the nitrophenylhydrazine plane, making a dihedral angle of 14.81 (8)°. The nitro and methoxy groups are each coplanar with the attached benzene rings. The nitrophenyl and methoxyphenyl groups are located on opposite sides of the C=N double bond, indicating an E configuration of the molecule. Adjacent molecules are linked together via N—H⋯O hydrogen bonding, forming chains along the [101] direction.

Crystals of the title compound, C 15 H 15 N 3 O 3 , were obtained from a condensation reaction of 4-nitrophenylhydrazine and 3-methoxyacetophenone. In the crystal structure, the methoxyphenyl ring is twisted slightly with respect to the nitrophenylhydrazine plane, making a dihedral angle of 14.81 (8) . The nitro and methoxy groups are each coplanar with the attached benzene rings. The nitrophenyl and methoxyphenyl groups are located on opposite sides of the C N double bond, indicating an E configuration of the molecule. Adjacent molecules are linked together via N-HÁ Á ÁO hydrogen bonding, forming chains along the [101] direction.

Comment
Since some phenylhydrazone derivatives have shown to be potential DNA damaging and mutagenic agents (Okabe et al., 1993), a series of new phenylhydrazone derivatives have been prepared in our laboratory (Shan et al., 2003a). As part of the ongoing investigation, the title compound has recently been prepared and its crystal structure is reported here.
The molecular structure of the title compound is shown in Fig. 1. The N1-C7 bond distance of 1.295 (2) Å indicates a typical C=N double bond. The molecule assumes an E configuration, with the nitrophenyl ring and methoxyphenyl rings located on the opposite sites of the C=N bond. The dihedral angle of 1.4 (3)° between nitro group and C10-benzene ring and the C1-C2-C3-C4 torsion angle of 0.9 (3)° suggest that nitro and methoxyl groups are co-planar with the individual benzene rings. The methoxyphenyl ring is slightly twisted with respect to the nitrophenylhydrazine mean plane by a small dihedral angle of 14.81 (8)°, indicating the molecule is approximately co-planar except for methyl H atoms.
Experimental 4-Nitrophenylhydrazine (0.31 g, 2 mmol) was dissolved in ethanol (10 ml), then H 2 SO 4 solution (98%, 0.5 ml) was added slowly to the ethanol solution with stirring. The solution was heated at about 333 K for several minutes until the solution cleared. An ethanol solution (5 ml) of 3-methoxyacetophenone (0.30 g, 2 mmol) was dropped slowly into the above solution with continuous stirring, and the mixture solution was kept at about 333 K for 0.5 h. When the solution had cooled to room temperature, red microcrystals appeared. They were separated and washed with cold water three times to get the product 0.45 g. Single crystals of the title compound were obtained by recrystallization from an absolute ethanol solution.

Refinement
Methyl H atoms were placed in calculated positions with C-H = 0.96 Å and the torsion angle was refined to fit the electron density, U iso (H) = 1.5U eq (C). Other H atoms were placed in calculated positions with C-H = 0.93 and N-H = 0.86 Å, and refined in riding mode with U iso (H) = 1.2U eq (C,N). Fig. 1. The molecular structure of the title compound with 30% probability displacement ellipsoids for non-H atoms.