4-Anilino-3-nitro-N-phenylbenzamide

In the title compound, C19H15N3O3, the anilino and benzamide rings make dihedral angles of 10.66 (16) and 50.39 (16)°, respectively, with the nitro-substituted benzene ring. The nitro group is slightly twisted by 11.49 (17)° with respect to the attached benzene ring. There is an intramolecular N—H⋯O hydrogen bond forming an S(6) ring. In the crystal, weak intermolecular N—H⋯O and C—H⋯O hydrogen bonds link the molecules into a chain parallel to the b axis. Futhermore, weak slipped π–π interactions [centroid–centroid distance = 3.819 (2) Å, interplanar distance = 3.567 Å and offset angle [how is the offset angle defined?] = 21°] between the anilino ring and its symmetry-related counterpart may help to stabilize the packing.

In the title compound, C 19 H 15 N 3 O 3 , the anilino and benzamide rings make dihedral angles of 10.66 (16) and 50.39 (16) , respectively, with the nitro-substituted benzene ring. The nitro group is slightly twisted by 11.49 (17) with respect to the attached benzene ring. There is an intramolecular N-HÁ Á ÁO hydrogen bond forming an S(6) ring. In the crystal, weak intermolecular N-HÁ Á ÁO and C-HÁ Á ÁO hydrogen bonds link the molecules into a chain parallel to the b axis. Futhermore, weak slippedinteractions [centroid-centroid distance = 3.819 (2) Å , interplanar distance = 3.567 Å and offset angle [how is the offset angle defined?] = 21 ] between the anilino ring and its symmetry-related counterpart may help to stabilize the packing.
Experimental 4-chloro-3-nitrobenzamide (4.5 g, 0.022 mol)was heat in 10 ml fresh distilled aniline for 18 h at 403 K. After reaction completed (TLC control) was added 50 ml e thanol, at room temperature. The red precipitate was sucked, washed with cold ethanol(2*15 ml), dried over sodium sulfate and gave 5.5 g(74%) (Schelz & Inst,1978). Pure compound (I) was obstained by crystallizing from methanol. Crystals of (I) suitable for X-ray diffraction were obstained by slow evaporation of an methanol solution.

Refinement
H atoms were positioned geometrically, with C-H = 0.93 Å for aromatic H, and constrained to ride on their parent atoms, with U iso (H) = 1.2U eq (C). Fig. 1. The molecular structure of (I), showing the atom-labeling scheme. Displacement ellipsoids are drawn at the 30% probability level. H atoms are represented as small spheres of arbitrary radii. Hydrogen bond is shown as dashed line.

Special details
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 Rfactors(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.