2-Nitro-N-propylbenzamide

The title compound, C10H12N2O3, contains three molecules in the asymmetric unit. In the crystal structure, intermolecular N—H⋯O interactions link the molecules into chains along the b axis. The crystal structure is consolidated by weak C—H⋯π interactions.


Related literature
The title compound is an agent for treating and preventing pains, see: Goodman & Serafini (2004). For bond-length data, see: Allen et al. (1987).

S1. Comment
The title compound is a kind of medicament for treating and preventing pains, and traumatic injuries such as traumatic brain injury and acute spinal cord injury (Goodman & Serafini, 2004). We herein report the crystal structure of the title compound (I).
In the molecule of (I), (Fig. 1), the bond lengths (Allen et al., 1987) and angles are within normal ranges. The title compound crystallized in the monolinic space group P2 1 /c, with three independent molecules (A, B and C) in the asymmetric unit.
In the crystal structure, intermolecular N-H···O interactions (Table 1) link the molecules into chains along the b axis ( Fig. 2), in which they may be effective in the stabilization of the structure. The crystal structure is consolidated by C-H···π hydrogen-bonding interactions (Table 1).

S2. Experimental
2-Nitro-N-propylbenzamide were dissolved in DMF (50 mL). The solution was then poured to ice water. The crystalline product was isolated by filtration, washed with water (600 ml), dried and give the product 1.8 g. The crystals of (I) were obtained by evaporating the acetone slowly at room temperature for about 14 d.

S3. Refinement
H atoms were positioned geometrically, with N-H = 0.86 and C-H = 0.93-0.97 Å, and constrained to ride on their parent atoms, with U iso (H) = 1.2 or 1.5U eq (C,N).  The one molecule of the three independent molecules in asymmetric unit, with the atom-numbering scheme.
Displacement ellipsoids are drawn at the 50% probability level.

Figure 2
A packing diagram for (I).

Special details
Experimental. 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 > 2sigma(F 2 ) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. Rfactors 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. Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. 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.