Crystal structure and Hirshfeld surface analysis of 6-benzoyl-3,5-diphenylcyclohex-2-en-1-one

The central cyclohexenone ring of the non-planar title compound adopts an envelope conformation. The crystal structure of the compound is stabilized by C—H⋯O and C—H⋯π interactions, forming a three-dimensional network.


Chemical context
There have been a series of significant examples of enone derivatives used as target products as well as synthetic intermediates (Abdelhamid et al., 2011;Asgarova et al., 2019;Khalilov et al., 2018a,b;Thomas, 2007). Moreover, a number of useful compounds containing enone moieties have been found in nature, such as cyanthiwigin U, (+)-cepharamine, phorbol and grandisine G, which were the object of a total synthesis (Pfeiffer et al., 2005;Schultz & Wang, 1998;Kawamura et al., 2016;Cuthbertson & Taylor, 2013). As part of a further study on the chemistry of ,-unsaturated ketones (Naghiyev et al., 2016), we report herein the crystal structure and Hirshfeld surface analysis of the title compound.

Figure 3
The Hirshfeld surface of the title compound plotted over d norm using a standard surface resolution with a fixed colour scale of À0.1582 (red) to 1.4399 a.u. (blue).

Synthesis and crystallization
To a solution of 1,3-diphenyl-2-propen-1-one (1.90 mmol) in benzene (15 ml), 1-phenylbutane-1,3-dione (1.90 mmol) and 0.05 ml of dry piperidine were added in this order, and the mixture was stirred at room temperature for 24 h. After completion of the reaction (as monitored by TLC), the solvent was removed under reduced pressure, and the residue was washed with hot water. Then, the products were recrystallized from ethanol (yield 72%, m.

Refinement
Crystal data, data collection and structure refinement details are summarized in Table 2. All H atoms were placed at calculated positions using a riding model, with C-H = 0.93-0.98 Å , and with U iso (H) = 1.2U eq (C). Owing to poor agreement between observed and calculated intensities, eighteen outliers (2 2 5)  The Hirshfeld surface of the title compound plotted over electrostatic potential energy in the range from À0.0500 to 0.0500 a.u. using the STO-3 G basis set at the Hartree-Fock level of theory. Hydrogen-bond donors and acceptors are shown as blue and red regions around the atoms, corresponding to positive and negative potentials, respectively.

6-Benzoyl-3,5-diphenylcyclohex-2-en-1-one
Crystal data 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.