1-Methyl-4-[(1E)-2-nitroprop-1-en-1-yl]benzene

The title compound, C10H11NO2, adopts an E conformation about the C=C bond. The C=C—C=C torsion angle is 32.5 (3)°. The crystal structure features weak intermolecular C—H⋯O interactions.

The title compound, C 10 H 11 NO 2 , adopts an E conformation about the C C bond. The C C-C C torsion angle is 32.5 (3). The crystal structure features weak intermolecular C-HÁ Á ÁO interactions.

Comment
Nitroalkenes are important organic intermediates, since they can be converted to synthetically useful N-and O-containing organic molecules, such as amines, aldehydes, carboxylic acids, or denitrated compounds (Ono, 2001;Berner et al., 2002;Ballini & Petrini, 2004). As a contribution in this field, we have synthesized a series of nitroalkenes by employing benzaldehydes and nitroethane (Yang et al., 2010). We report here the crystal structure of the title compound (Fig. 1).

Experimental
To a solution of p-tolualdehyde (50 mmol) in AcOH (25 mL), nitroethane (75 mmol) was added, followed by butylamine (100 mmol, 7.4 mL). The mixture was sonicated at 60 °C, until GC showed full conversion of the aldehyde. The mixture was poured into ice water, the precipitate was filtered off, washed with water and recrystallized from EtOH/EtOAc to give the final product. Single crystals were obtained by slow evaporation of a n-hexane/EtOAc (10:1, v/v) solution.

Refinement
All H atoms were placed in calculated positions and refined using a riding model, with C-H = 0.93 Å and U iso (H) = 1.2U eq (C) for aromatic H atoms, and with C-H = 0.96 Å and U iso (H) = 1.5U eq (C) for methyl H atoms.

Figure 2
View of the intermolecular interactions illustrated as dashed lines. Refinement. Refinement of F 2 against ALL reflections. The weighted R-factor wR and goodness 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 threshold expression of F 2 > σ(F 2 ) is used only for calculating R-factors(gt) 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.