Synthesis, crystal structure, spectroscopic features and Hirshfeld surfaces of 2-methyl-3-[(2-methylphenyl)carbamoyl]phenyl acetate

2-Methyl-3-[(2-methylphenyl)carbamoyl]phenyl acetate was synthesized, characterized by IR spectroscopy, and its crystal structure was determined from single-crystal data. In the crystal, molecules are linked by N—H⋯O hydrogen bonds. The two independent molecules in the asymmetric unit adopt different conformations.

The title compound, C 17 H 17 NO 3 , was synthesized, characterized by IR spectroscopy and its crystal structure was determined from single-crystal diffraction data. The asymmetric unit contains two molecules, which adopt different conformations. In one molecule, the acetoxy and the terminal 2-methylphenyl groups are positioned on opposite sides of the plane formed by the central benzene ring, whereas in the other molecule they lie on the same side of this plane. In the crystal, the molecules are linked through strong N-HÁ Á ÁO hydrogen bonds into chains along [010]. Hirshfeld surface analysis and fingerprint plots were used to investigate the intermolecular interactions in the solid state.

Structural commentary
The asymmetric unit of the title compound ( Fig. 1) contains two molecules, A and B, which adopt different conformations that can be characterized by the mutual arrangement of the acetoxy and terminal 2-methylphenyl groups with respect to ISSN 2056-9890 the plane of the central benzene ring: in molecule A they lie on different sides of this plane, whereas in molecule B they are positioned on the same side. The torsion angles characterizing the conformation details are summarized in Table 1. The dihedral angles subtended by the aromatic rings are 54.33 (12) and 66.68 (11) in molecules A and B, respectively. The molecular conformations are stabilized by weak intramolecular C-HÁ Á ÁO contacts (Table 2). All bond lengths and angles are typical of similar compounds, bearing in mind the effect of intermolecular hydrogen bonds on the geometry of the amido groups.

Supramolecular features
The packing diagram of the title compounds is presented in Fig. 2. In the crystal, the molecules are linked through strong N-HÁ Á ÁO hydrogen bonds (Table 2) into chains along [010]. They are further linked by C-HÁ Á ÁO and C-HÁ Á Á contacts (Table 2).

Database survey
A search in the Cambridge Structural Database (CSD version 5.39, update of August 2018; Groom et al., 2016) for 3-acetoxy-N-phenylbenzamide derivatives gave three hits: 3-acetoxy-2methyl-N-(4-methylphenyl)benzamide (HEJBIK; Kırca et al., 2018), 3-acetoxy-2-methyl-N-phenylbenzamide and 3-acetoxy-2-methyl-N-(4-methoxyphenyl)benzamide (HEJBOQ and JUMCEB, respectively; both Demir et al., 2015). The structure of HEJBIK is especially close to that of the title compound: it also contains two molecules in an asymmetric unit and is isostructural to the title compound with the exception of one methyl group (2-Me in the title compound and 4-Me in HEJBIK). The two independent molecules in HEJBIK have different conformations in the same manner, as in the title structure. In the two structures HEJBOQ and JUMCEB, the acetoxy groups and the terminal benzene rings are positioned on opposite sides of the planes formed by the central benzene rings. In all these structures, the molecules are linked into chains by N-HÁ Á ÁO hydrogen bonds.

Figure 1
The asymmetric unit of the title compound, with displacement ellipsoids drawn at the 50% probability level.

Hirshfeld surface analysis
The molecular Hirshfeld surfaces (d norm ) for molecules A and B of the title compound generated using CrystalExplorer3.1 (Wolff et al., 2012) and are presented in Fig. 3. The d norm values are mapped on the Hirshfeld surfaces using a red-blue-white colour scheme (Spackman & Jayatilaka, 2009)   The fingerprint plots for molecule B: (a) all atoms inside Á Á Áall atoms outside (100%),  The fingerprint plots for molecule A: (a) all atoms inside Á Á Áall atoms outside n (AE0.25 a.u.) is shown in Fig. 6 where blue regions correspond to positive electrostatic potential and red spots related to the oxygen atoms represent the areas of negative electrostatic potential; the distribution is analogous to that in a similar compound (Yaman et al., 2018).

Vibrational spectrum
The IR spectrum of the title compound (KBr, cm À1 ) shown in

Synthesis and crystallization
The synthesis was performed according to the reaction scheme presented in Fig. 8 and applied earlier for the synthesis of analogous compounds (Cakmak et al., 2016;Kırca et al., 2018, Demir et al., 2015. A solution of 3-acetoxy-2-methylbenzoyl chloride (11 mmol) in THF (10 mL) was added dropwise to a solution of 2-methylaniline (10 mmol) and triethylamine (10 mmol) in THF (10 mL) at room temperature. After the reaction mixture had been stirred at room temperature for 15 h, the resulting white precipitate was filtered off and then 100 ml of water was added dropwise to the filtrate. The precipitate was filtered off and washed several times with water to remove the unreacted reagents and triethylamine hydrochloride. The crude product was recrystallized from acetonitrile (1.82 g, 58%; m.p. 435-438 K). Single crystals were obtained from an acetonitrile solution after incubation in the fridge for 20 days.

Refinement
Crystal data, data collection and structure refinement details are summarized in IR spectrum of the title compound.