4-Methoxy-N-methylbenzamide

In the title compound, C9H11NO2, the dihedral angle between the amide group and the benzene ring is 10.6 (1)°. In the crystal, molecules are connected via N—H⋯O hydrogen bonds, supported by a C—H⋯O contact, forming chains along b. These chains are linked by C—H⋯π interactions to give a three-dimensional network.

In the title compound, C 9 H 11 NO 2 , the dihedral angle between the amide group and the benzene ring is 10.6 (1) . In the crystal, molecules are connected via N-HÁ Á ÁO hydrogen bonds, supported by a C-HÁ Á ÁO contact, forming chains along b. These chains are linked by C-HÁ Á Á interactions to give a three-dimensional network.

Related literature
The title compound is an important intermediate in organic synthesis. For background to applications of the title compound and the synthesis, see: Lee et al. (2009). For bondlength data, see: Allen et al. (1987).  Table 1 Hydrogen-bond geometry (Å , ).

Experimental
The title compound, (I) was prepared by a literature method (Lee et al., 2009). Crystals were obtained by dissolving (I) (0.2 g) in methanol (50 ml) and evaporating the solvent slowly at room temperature for about 10 d.

Refinement
All H atoms were positioned geometrically and constrained to ride on their parent atoms, with C-H = 0.93 Å for aromatic H, 0.96 Å for methyl H and 0.86 Å for N-H, respectively. The U iso (H) = xU eq (C), where x = 1.2 for aromatic H and N-H, and x = 1.5 for methyl H.

Computing details
Data collection: CAD-4 Software (Enraf-Nonius, 1985); cell refinement: CAD-4 Software (Enraf-Nonius, 1985); data reduction: XCAD4 (Harms & Wocadlo, 1995); 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: SHELXTL (Sheldrick, 2008).  The molecular structure of (I), with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.  A packing diagram of (I). where P = (F o 2 + 2F c 2 )/3 (Δ/σ) max < 0.001 Δρ max = 0.18 e Å −3 Δρ min = −0.19 e Å −3 Extinction correction: SHELXL97 (Sheldrick, 2008), Fc * =kFc[1+0.001xFc 2 λ 3 /sin(2θ)] -1/4 Extinction coefficient: 0.25 (2) Special details Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å 2 )
x y z U iso */U eq N −0.0727 (2)