Hirshfeld surface analysis and crystal structure of N-(2-methoxyphenyl)acetamide

The title compound, C9H11NO2, was synthesized and characterized in the solid state. The molecular Hirshfeld surfaces were obtained to determine the interactions between the molecules and explore the nature of the packing of the molecules in the crystal.


Chemical context
The amide function is one of the most important linkages in natural chemistry. It is the key linker in peptides and a number of polymers, and is additionally found in numerous pharmaceuticals and other items (Dam et al., 2010) with natural activity, including about 25% of commercially available drugs. Consequentially, the amide bond is a standout amongst the most vital changes in a current natural blend (Ojeda-Porras & Gamba-Sá nchez, 2016). In the light of such discoveries, we report the crystal structure of the title compound.

Structural commentary
The molecular structure of the asymmetric unit of the C 9 H 11 NO 2 compound is shown in Fig. 1. The N1-C2, C2-O2 and C2-C1 bond lengths are 1.347 (2), 1.2285 (19) and 1.480 (3) Å , respectively. The C2-O2 bond in the amide group shows partial double-bond character and is similar in length to those found in amide compounds in the literature benzene ring is planar with an r.m.s. deviation of 0.0019. The amide group is not coplanar with the benzene ring, as shown by the C3-N1-C2-O2 and C3-N1-C2-C1 torsion angles of À2.5 (3) and 176.54 (19) , respectively.

Supramolecular features
In the crystal, adjacent molecules are linked by weak C-HÁ Á ÁO hydrogen bonds, forming supramolecular chains propagating along the a-axis direction (Table 1 and Fig. 2). The chains are further connected by weak C-HÁ Á Á interactions.

Hirshfeld surface analysis
Hirshfeld surface analysis (Spackman & Jayatilaka, 2009) and the associated two-dimensional fingerprint plots (McKinnon et al., 2007) were generated using CrystalExplorer17 (Turner et al., 2017). Plots of the Hirshfeld surface mapped over d norm , d i and d e using a fixed colour scale of À0.5051 (red) to 1.2978 (blue) a.u. are shown in Fig. 3.. The red spots in the d norm plot indicate the intermolecular contacts associated with the strong hydrogen bonds and interatomic contacts such as N-HÁ Á ÁO.  Table 1 Hydrogen-bond geometry (Å , ).

Figure 2
A partial view of the crystal packing. Dashed lines denote the intermolecular C-HÁ Á ÁO and N-HÁ Á ÁO hydrogen bonds (Table 1).

Figure 3
The Hirshfeld surface of the title compound mapped over d norm , d i and d e .

Figure 1
The asymmetric unit of the title compound with displacement ellipsoids drawn at the 50% probability level. contacts is observed to be highest towards the Hirshfeld surface with a 53.9% contribution. The contribution from the C-HÁ Á ÁO hydrogen bond (21.4% contribution) appears as a pair of sharp spikes at d e + d i =1.9 Å . A view of the threedimensional Hirshfeld surface plotted over electrostatic potentials in the range À0.1028 to 0.1158 a.u. is shown in Fig. 6. The hydrogen-bond donors and acceptors are showed as blue and red regions around the atoms corresponding to positive and negative potentials, respectively.

Synthesis and crystallization
This compound was formed as by-product in the synthesis of a benzamide derivative from the reaction between an oxazolone with o-methoxyaniline (Samad & Hawaiz, 2019) in the presence of acetic acid as solvent. The reaction mixture was refluxed for 2 h, cooled, poured into water, filtered and dried. The remaining filtrate was left for seven days to obtain goodquality crystals.

Refinement
Crystal data, data collection and structure refinement details are summarized in Table 2     The view of the three-dimensional Hirshfeld surface of the title compound plotted over the electrostatic potentials. 0.93 Å for aromatic H atoms, C-H = 0.96 Å for methyl H atoms, and with U iso (H) = 1.2-1.5 U eq (C).  (Farrugia, 2012) and Mercury (Macrae et al., 2006); software used to prepare material for publication: SHELXL2018 (Sheldrick, 2015b), WinGX (Farrugia, 2012) and PLATON (Spek, 2009).

N-(2-Methoxyphenyl)acetamide
Crystal data where P = (F o 2 + 2F c 2 )/3 (Δ/σ) max < 0.001 Δρ max = 0.13 e Å −3 Δρ min = −0.12 e Å −3 Special details Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å 2 )