1-(3,5-Dimethoxybenzyl)-1H-pyrrole

The title compound, C13H15NO2, was synthesized from 3,5-dimethoxybenzaldehyde. The dihedral angle between the pyrrole and benzene rings is 89.91 (5)°. In the crystal, weak C—H⋯O and C—H⋯π interactions link the molecules into a three-dimensional network.

compound may possess the same qualities. The title compound is prepared via two steps and the product of the first step can be added to the solution of the second step without purification.
In the title compound, as shown in Fig. 1, the pyrrole and benzene rings are on the different plane. The dihedral angle between the two plane is 89.91 (5)° and close to the dihedral angle in 1-benzyl-N-methyl-1H-pyrrole-2-carboxamide (Wang et al., 2011). The N-C5-C6-C7 torsion angle is 26.37 (20)°. The structure is stabilized by the non-classical hydogen bonds (Table 1). The packing diagram is presented in Fig. 2.

Experimental
Starting material is 3,5-dimethoxy-benzaldehyde (20.9 g, 126 mmol) (Fig. 3). For the first step, 3,5-dimethoxy-benzylamine is prepared according to (Yraola et al., 2006). 2,5-Dimethoxytetrahydrofuran (14.2 g, 108 mmol) and glacial acetic acid (150 ml) were added to the first step product. After stirring at 333 K for 6 h, solvent was removed under reduced pressure. The crude product was purified by flash column chromatography (petrol ether / EtOAc (10 / 1), yielding the title compound (0.98 g, 52%) as a white solid. The product (16 mg) was dissolved in ethyl ether (1 ml) and methanol (0.05 ml). Single crystals suitable for X-ray diffraction experiment was obtained from the solution by cooling at 273 K for seven days. The molecule was characterized by NMR ( Fig. 4).

Refinement
All H atoms attached to C atoms were treated as riding, withC-H = 0.96Å for methyl group, C-H = 0.97Å for methylene group, and C-H = 0.93Å for aromatic ring, with U iso (H) = 1.2U eq (C) of the carrier atoms to which they are attached and U iso (H) = 1.5U eq (C) for the methyl groups.  The molecular structure of title compound, showing the atom numbering scheme. Displacement ellipsoids are drawn at 30% probability level. H atoms are presented as a small spheres of arbitrary radius.

Figure 2
A view of the packing of the title compound along b axis.

Figure 3
The synthetic route of the title compound.  The structure of title compound, with atoms labeling corresponding to the characterization by NMR. where P = (F o 2 + 2F c 2 )/3 (Δ/σ) max = 0.014 Δρ max = 0.15 e Å −3 Δρ min = −0.18 e Å −3 Special details Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 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.