N-(4-Nitrophenyl)cinnamamide

In the molecule of the title compound, C15H12N2O3, the dihedral angle between the rings is 3.04 (8)°. The central NOC3 fragment is planar [maximum deviation = 0.005 (3) Å] and is oriented at dihedral angles of 8.23 (8) and 7.29 (9)° with respect to the phenyl and nitrophenyl rings, respectively. In the crystal structure, intermolecular N—H⋯O and C—H⋯O interactions link the molecules into a two-dimensional network. π–π contacts between rings [centroid–centroid distance = 3.719 (1) Å] may further stabilize the structure.

A search of the Cambridge Crystallographic Database (CSD version 5.30; Allen, 2002) for a fragment containing the title compound without NO 2 group revealed only four entries containg the basic skeleton of the title compound with refcodes: DIPHUF (Peeters et al., 1986), EHATUC and EHAVAK (Nissa et al., 2002) and FALQAL (Nissa et al., 2004).
In the molecule of the title compound ( Fig. 1), rings A (C1-C6) and B (C10-C15) are, of course, planar and they are oriented at a dihedral angle of A/B = 3.04 (8)°. The (O1/N1/C7-C9) moiety is planar with a maximum deviation of -0.005 (3) Å for atom C8 and it is oriented with respect to rings A and B at dihedral angles of 8.23 (8) and 7.29 (9) °, respectively.
In the crystal structure, intermolecular N-H···O and C-H···O interactions (Table 1) link the molecules into a two dimensional network (Fig. 2), in which they may be effective in the stabilization of the structure. The π-π contact between the phenyl rings, Cg1-Cg2 i [symmetry code: (i) 1 -x, y -1/2, 1/2 -z, where Cg1 and Cg2 are centroids of the rings A (C1-C6) and B (C10-C15), respectively] may further stabilize the structure, with centroid-centroid distance of 3.719 (1) Å.

Experimental
For the preparation of the title compound, cinnamic acid was converted into cinnamoyl chloride using the standard procedure.
A stirred solution of cinnamoyl chloride (5.4 mmol) in CHCl 3 was treated with p-nitroaniline (21.6 mmol) under a nitrogen atmosphere at reflux for 4 h. Upon cooling, the reaction mixture was diluted with CHCl 3 and washed consecutively with aq 1.0 M HCl and saturated aq NaHCO 3 . The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. Crystallization of the residue in MeOH afforded the title compound (yield; 81%) as colorless crystals: Anal. calcd. for C 15 H 12 N 2 O 3 : C, 67.16; H, 4.51; N, 10.44; found: C, 67.21; H, 4.59; N, 10.41.

Refinement
H atoms were positioned geometrically with N-H = 0.88 Å (for NH) and C-H = 0.95 Å for aromatic H atoms, respectively, and constrained to ride on their parent atoms, with U iso (H) = 1.2U eq (C,N). Fig. 1. The molecular structure of the title molecule with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level