4-Dimethylamino-1-(4-methoxyphenyl)-2,5-dioxo-2,5-dihydro-1H-pyrrole-3-carbonitrile

In the title compound, C14H13N3O3, a twist occurs, as seen in the dihedral angle of 53.60 (12)° between the pyrrole and benzene rings. A three-dimensional architecture is formed in the crystal whereby layers of molecules in the ac plane are connected by C—H⋯O and C—H⋯π interactions.


R. T. Tiekink Comment
The title compound (I) was investigated owing to the biological activities exhibited pyrroles and pyranopyrrole analogues (Amer et al. 2009;Amer et al. 2008). Herein, its crystal structure determination is described.
In (I), Fig. 1, the dihedral angle of 53.60 (12)° between the pyrrole (r.m.s. deviation = 0.005 Å) and benzene rings indicates a significant twist in the molecule. The methoxy substituent is twisted out of the plane of the ring to which it is attached as seen in the value of the C14-O3-C11-C10 torsion angle of -13.9 (4)°. The dimethylamino group is also slightly twisted out of the plane through the pyrrole ring to which it is attached; the C5-N2-C2-C1 torsion angle is 8.7 (3)°.
The three-dimensional architecture of (I) is consolidated by C-H···O interactions, involving both carbonyl-O atoms, as well as C-H···π interactions whereby the benzene ring serves as a bridge between molecules, Fig. 2 and Table 1.

Refinement
Carbon-bound H-atoms were placed in calculated positions (C-H 0.93 to 0.96 Å) and were included in the refinement in the riding model approximation, with U iso (H) = 1.2U equiv (C).

Computing details
Data collection: CrysAlis PRO (Agilent, 2011); cell refinement: CrysAlis PRO (Agilent, 2011); data reduction: CrysAlis PRO (Agilent, 2011); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: publCIF (Westrip, 2010).  The molecular structure of (I) showing displacement ellipsoids at the 35% probability level. 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.