N-(1,5-Dimethyl-3-oxo-2-phenyl-2,3-di-hydro-1H-pyrazol-4-yl)-2-(4-nitro-phen-yl)acetamide

Abstract

In the title compound, C19H18N4O4, the nitro-phenyl and phenyl rings are twisted by 67.0 (6) and 37.4 (4)°, respectively, with respect to the pyrazole ring plane [maximum deviation = 0.0042 (16) Å]. The dihedral angle between the mean planes of the phenyl rings is 59.3 (3)°. The amide group, with a C-N-C-C torsion angle of 177.54 (13)°, is twisted away from the plane of the pyrazole ring in an anti-periplanar conformation. In the crystal, N-H⋯O hydrogen bonds involving the carbonyl group on the pyrazole ring and the amide group, together with weak C-H⋯O inter-actions forming R 2 (2)(10) graph-set motifs, link the mol-ecules into chains along [100]. Additional weak C-H⋯O inter-actions involving the nitro-phenyl rings further link the mol-ecules along [001], also forming R 2 (2)(10) graph-set motifs, thereby generating (010) layers.

Fig. 1.

ORTEP drawing of (I) (C19H18N4O4) showing the labeling scheme of the molecule with 30% probability displacement ellipsoids.

Fig. 2.

Molecular packing for (I) viewed along the b axis. Dashed lines indicate N—H···O intermolecular hydrogen bonds and weak C—H···O intermolecular interactions forming R22(10) graph set motifs linking the molecules into chains along [100]. Additional weak C—H···O intermolecular interactions involving the nitrophenyl rings link the molecules further along [001] also forming R22(10) graph set motifs viewed with dashed lines. H atoms not involved in hydrogen bonding have been removed for clarity.

Fig. 3.

Synthesis scheme of (I).