Crystal structure and Hirshfeld surface analysis of 2-(4-bromophenyl)-4-methyl-6-oxo-1-phenyl-1,6-dihydropyridine-3-carbonitrile

Molecules in the crystal are connected along the c-axis direction by C—Br⋯π interactions, resulting in zigzag chains parallel to the (010) plane. C—H⋯N and C—H⋯O hydrogen-bonding interactions further connect the molecules, forming a three-dimensional network and reinforcing the molecular packing.


Supramolecular features and Hirshfeld surface analysis
CrystalExplorer17.5 (Turner et al., 2017) was used to analyse and visualize the intermolecular interactions of the title compound. Fig. 6a,b depicts the front and back sides of the Hirshfeld surface plotted over d norm in the range of À0.2437 to 1.2589 a.u. The red spots on the Hirshfeld surface indicate C-HÁ Á ÁN and C-HÁ Á ÁO interactions (Table 1).
The overall two-dimensional fingerprint plot for the title compound and those delineated into HÁ Á ÁH (36.2%, Fig. 7b The molecular structure of the title compound. Displacement ellipsoids are drawn at the 50% probability level.
In the crystal of XOZCUL (Shishkina et al., 2009), the pyridine-3-carboxylate molecules form layers parallel to (010), which are linked by hydrogen bonds mediated by the bridging solvate molecules.

Synthesis and crystallization
To a solution of 3-(4-bromophenyl)-3-oxopropanenitrile (1.14 g; 5.1 mmol) and acetoacetanilide (0.92 g; 5.2 mmol) in methanol (25 mL), methylpyperazine (3 drops) was added and the mixture was stirred at room temperature for 48 h. Then 15 mL of methanol were removed from the reaction mixture, which was left overnight. The precipitated crystals were separated by filtration and recrystallized from ethanol/water

Funding information
This study was supported by Baku State University and the Ministry of Science and Higher Education of the Russian Federation [award No. 075-03-2020-223 (FSSF-2020].

Special details
Experimental. CrysAlisPro 1.171.41.117a (Rigaku OD, 2021) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. 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.