Crystal structure and Hirshfeld surface analysis of (2E)-1-(3-bromophenyl)-3-(4-fluorophenyl)prop-2-en-1-one

In the title compound, the 3-bromophenyl and 4-fluorophenyl rings, linked via a prop-2-en-1-one spacer, make a dihedral angle of 48.90 (15)°. In the crystal, molecules are linked by C—H⋯π interactions between the bromophenyl and fluorophenyl rings of molecules, resulting in a two-dimensional layered structure parallel to the ab plane.

In the title compound, C 15 H 10 BrFO, the molecular structure consists of a 3-bromophenyl ring and a 4-fluorophenyl ring linked via a prop-2-en-1-one spacer. The 3-bromophenyl and 4-fluorophenyl rings make a dihedral angle of 48.90 (15) . The molecule has an E configuration about the C C bond and the carbonyl group is syn with respect to the C C bond. In the crystal, molecules are linked by C-HÁ Á Á interactions between the bromophenyl and fluorophenyl rings of molecules, resulting in a two-dimensional layered structure parallel to the ab plane. The molecular packing is stabilized by weak BrÁ Á ÁH and FÁ Á ÁH contacts, one of which is on the one side of each layer, and the second is on the other. The intermolecular interactions in the crystal packing were further analysed using Hirshfeld surface analysis, which indicates that the most significant contacts are ClÁ Á ÁH/HÁ Á ÁCl (20.8%), followed by CÁ Á ÁH/HÁ Á ÁC (31.1%), HÁ Á ÁH (21.7%), BrÁ Á ÁH/HÁ Á ÁBr (14.2%), FÁ Á ÁH/HÁ Á ÁF (9.8%), OÁ Á ÁH/ HÁ Á ÁO (9.7%).

Supramolecular features and Hirshfeld surface analysis
In the crystal, molecules are linked by C-HÁ Á Á interactions between the bromophenyl and fluorophenyl rings of molecules, resulting in a two-dimensional layered structure parallel to the ab plane (Table 1; Fig. 2). The molecular packing is stabilized by weak BrÁ Á ÁH and Á Á ÁH contacts, one of which is on the one side of a layer, and the second is on the other. A summary of the short contacts is given in Table 2.
Hirshfeld surfaces and fingerprint plots were generated for the title compound using CrystalExplorer  Table 1 Hydrogen-bond geometry (Å , ).

Figure 2
A view of the C-HÁ Á Á interactions in the title compound.

Figure 1
The molecular structure of the title compound, showing the atom labelling and displacement ellipsoids drawn at the 50% probability level. Table 2 Summary of short interatomic contacts (Å ) in the title compound.
3.00 2 À x, Ày, 1 À z sity, representing short or long contacts and indicating the relative strength of the interactions. The function d norm is a ratio enclosing the distances of any surface point to the nearest interior (d i ) and exterior (d e ) atom and the van der Waals radii of the atoms (Hirshfeld, 1977;Soman et al., 2014). The function d norm will be equal to zero when intermolecular distances are close to van der Waals contacts. They are indicated by a white colour on the Hirshfeld surface, while contacts longer than the sum of van der Waals radii with positive d norm values are coloured in blue. The surface plot for d norm (Fig. 3) was generated using a high standard surface resolution over a colour scale of À0.0186 to 1.3784 a.u.
The overall two-dimensional fingerprint plot for the title compound and those delineated into CÁ Á ÁH/HÁ Á ÁC, HÁ Á ÁH, BrÁ Á ÁH/HÁ Á ÁBr, FÁ Á ÁH/HÁ Á ÁF and OÁ Á ÁH/HÁ Á ÁO contacts are illustrated in Fig. 4. The percentage contributions of the various interatomic contacts to the Hirshfeld surfaces are given in Table 3. The presence of C-HÁ Á Á interactions in the crystal is indicated by the pair of characteristic wings in the fingerprint plot delineated into CÁ Á ÁH/HÁ Á ÁC contacts (31.1% contribution to the Hirshfeld surface). The CÁ Á ÁH/HÁ Á ÁC interactions are represented by the spikes at the bottom right and left (d e + d i ' 2.75 Å ). HÁ Á ÁH contacts are disfavoured when the number of H atoms on the molecular surface is large.

Synthesis and crystallization
The title compound was synthesized as per the procedure reported earlier (Kumar et al., 2013a,b The two-dimensional fingerprint plots of the title compound.

Figure 3
A view of the Hirshfeld surface of the title compound mapped over d norm , using a fixed colour scale of À0.0186 (red) to 1.3784 (blue) a.u. 342 K) was determined using a Stuart Scientific (UK) apparatus.

(2E)-1-(3-Bromophenyl)-3-(4-fluorophenyl)prop-2-en-1-one
Crystal data C 15 H 10 BrFO M r = 305.14 Triclinic, P1 a = 5.9255 (6)  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.