2-Methyl-N-[1-(1H-pyrrol-2-yl)ethylidene]aniline

There are two independent molecules in the asymmetric unit of the title compound, C13H14N2, in which the dihedral angles formed by the pyrrole and benzene rings are 83.63 (8) and 87.84 (8)°. In the crystal, molecules are linked via pairs of N—H⋯N hydrogen bonds, forming inversion dimers, which are further connected by C—H⋯π interactions.

There are two independent molecules in the asymmetric unit of the title compound, C 13 H 14 N 2 , in which the dihedral angles formed by the pyrrole and benzene rings are 83.63 (8) and 87.84 (8) . In the crystal, molecules are linked via pairs of N-HÁ Á ÁN hydrogen bonds, forming inversion dimers, which are further connected by C-HÁ Á Á interactions.
Data collection: APEX2 (Bruker,2008); cell refinement: SAINT (Bruker,2008); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: publCIF (Westrip, 2010).  (Kazushi & Hayato, 2005). Being the typical kind of iminopyrrole units, bis(imino)pyridine incorporated late transition metal catalysts have been investigated due to their antioxidant properties and outstanding activities for olefin polymerization. As a five-membered analogue of the pyridine ring (He et al., 2009), pyrrole has been frequently introduced into the skeleton of bis(imino)pyridine ligands to design new ligands and corresponding metal complexes (Britovsek et al., 2003;Dawson et al., 2000). As a part of our ongoing studies on mono(imino)pyrrole ligands (Su et al., 2009a,b), we report herein the crystal structure of the title compound, which crystallizes with two unique molecules, A & B, in the asymmetric unit ( Fig. 1).
In the title compound, the dihedral angles formed by the pyrrole and benzene rings are 83.63 (8) Table 1, Cg1 and Cg2 are the centroids of benzene rings in the molecule A and B, respectively).

Experimental
The reagents 2-acetyl pyrrole (0.1528 g, 1.40 mmol), o-toluidine (0.3000 g, 2.80 mmol) were placed in a 50-ml flask, after a few drops of acetic acid was added in, the mixture was subjected to radiation in a 800 W microwave oven for 3 min and 2 min on a medium-heat setting. The reaction was monitored by TLC, and the crude product was purified by silica gel column chromatography (eluant: petroleum ether/ethyl acetate, 5:1 v/v), the colourless crystals of the title compound were at last obtained by recrystallization from ethanol (yield 0.1136 g, 40.91%). m.p. 396.5-398.9 K. Plate like colourless single crystals used in X-ray diffraction studies were grown in the mixture solvents of water and ethanol.

Refinement
All H atoms were placed at calculated positions and refined as riding, with C-H = 0.93-0.96 Å, N-H = 0.86 Å, and with U iso (H) = 1.2 U eq (C, N) or 1.5 U eq (C) for methyl H atoms. The positions of methyl hydrogens were optimized rotationally.