5-Methyl-2-nitro-aniline

Abstract

The bond lengths and angles within the title mol-ecule, C₇H₈N₂O₂, conform to average values for other 5-substituted-2-nitro-anilines, and with those calculated by a DFT geometry optimization. The short C-NH₂ bond length of 1.3469 (12) Å is indicative of substantial involvement of the aniline N-atom in the aromatic π bonding system of the ring. In the extended structure, N-H⋯O hydrogen bonds link the mol-ecules into [001] tapes, which aggregate into zipper-like folded ribbons. Layers of parallel ribbons stack along a to complete the structure.

Keywords: DFT geometry optimization; crystal structure; hydrogen bonding.

Figure 1

Displacement ellipsoid plot at the 50% probability level of (I) with atom labels. The intra­molecular N—H⋯O hydrogen bond is indicated by a dashed line.

Figure 2

Plot of the highest occupied mol­ecular orbital for (I) from the DFT geometry optimization.

Figure 3

Electrostatic potential plot for (I) from the DFT geometry optimization. Red indicates accumulation of negative charge and blue accumulation of positive charge.

Figure 4

Packing diagram for a corrugated sheet of mol­ecules of (I) viewed down a with b horizontal and c vertical. Atoms are drawn as circles of arbitrary radii, intra­molecular hydrogen bonds are indicated by thick dashed lines, and inter­molecular hydrogen bonds are indicated by thin dashed lines.

Figure 5

Unit-cell packing diagram for (I) viewed down c with a vertical and b horizontal. Atoms are drawn as circles of arbitrary radii.