(E)-1-(3-Nitrophenyl)ethanone (2-methylphenyl)hydrazone

In the title Schiff base compound, C15H15N3O2, the azomethine double bond adopts an E configuration. The dihedral angle between the two aromatic rings is 13.4 (12)°. In the crystal, molecules are arranged in wave-like layers parallel to (100) without any classical hydrogen bonding.

In the title Schiff base compound, C 15 H 15 N 3 O 2 , the azomethine double bond adopts an E configuration. The dihedral angle between the two aromatic rings is 13.4 (12) . In the crystal, molecules are arranged in wave-like layers parallel to (100) without any classical hydrogen bonding.

Comment
Schiff bases represent an important class of organic compounds, with a wide range of biological properties including antifungal, antibacterial, herbicidal, antiproliferative, cytotoxic, anticonvulsant and anticancer activities (Khan et al., 2009;Gerdemann et al., 2002;Mallikarjun & Sangamesh, 1997;Solomon & Lowery, 1993). They are also known as important intermediates formed during the process of glycation (reaction of protein and glucose) undergoing rearrangement to form more stable Amadori products, which are considered as therapeutic targets to treat diabetes and its complications (Ahmad et al., 2007;Ahmed, 2005). During our on going search for effective antiglycating agents, the title compound was prepared and crystallized.
The structure of title compound ( Fig. 1) is not planar, the dihedral angle between the aromatic rings (C1-C6 and C8-C13) being 13.4 (12)°. The azomethine (C7═N2) double bond adopts an E configuration, with the N1-N2-C7-C6 torsion angle of 178.38 (16)°. The bond lengths and angle are similar to those observed in other structurally related compounds (Fun et al., 2008;Tezcan et al., 2004). In the crystal structure, the molecules are arranged in wave-like layers parallel to the (100) plane ( Fig. 2) without any classical intermolecular hydrogen bonding.

Experimental
The synthesis of title compound I was carried out by refluxing a mixture of 3-nitroacetophenone (165 mg, 1 mmol) and 1-(2-methylphenyl)hydrazine hydrochloride (159 mg, 1 mmol) with acetic acid (1 ml) in ethanol (10 ml) for 18 h. The progress of reaction was monitored by TLC. After cooling and filtration the crystalline product was collected, washed with hexane and dried to afford the title compound in 85% yield. Recrystallization from ethanol afforded yellowish crystals suitable for single-crystal X-ray diffraction studies. All chemicals were purchased from Sigma-Aldrich.

Refinement
H atoms on methyl and methine groups were positioned geometrically with C-H = 0.96 and 0.93 Å respectively, and constrained to ride on their parent atoms with U iso (H) = 1.2U eq (C) or 1.5U eq (C) for methyl H atoms. The hydrazone H atom was located in a difference Fourier map and refined isotropically. A rotating group model was applied to the methyl groups.