Crystal structure and Hirshfeld surface analysis of 4-(4-methylbenzyl)-6-phenylpyridazin-3(2H)-one

In the title compound, intermolecular N—H⋯O hydrogen bonds link the molecules into a three-dimensional supramolecular network.


Chemical context
Pyridazines are an important family of six-membered aromatic heterocycles containing two N atoms. Pyridazinone is an important pharmacophore possessing a wide range of biological applications (Asif, 2014;Akhtar et al., 2016). The chemistry of pyridazinones has been an interesting field of study for decades and this nitrogen heterocycle has become a scaffold of choice for the development of potential drug candidates (Dubey & Bhosle, 2015;Thakur et al., 2010). A review of the literature has revealed that substituted pyridazinones have received a lot of attention in recent years because of their significant potential as antimicrobial (Sö nmez et al., 2006), antidepressant (Boukharsa et al., 2016), antiinflammatory (Barberot et al., 2018), antihypertensive (Siddiqui et al., 2011), analgesic (Gö kçe et al., 2009, anti-HIV (Livermore et al., 1993), anticonvulsant (Partap et al., 2018;Sharma et al., 2014), cardiotonic (Wang et al., 2008), antihistaminic (Tao et al., 2012), glucan synthase inhibitors (Zhou et al., 2011), phosphodiesterase (PDE) inhibitors (Ochiai et al., 2012) and herbicidal agents (Asif, 2013). In continuation of our work in this field (El Kali et al., 2019;Chkirate et al., 2019a,b;Karrouchi et al., 2015Karrouchi et al., , 2016a, we report the synthesis and the crystal and molecular structures of the title compound, as well as an analysis of its Hirshfeld surface.

Figure 1
The molecular structure of the title compound, with the atom labelling. Displacement elipsoids are drawn at the 20% probability level.
buting 56.6% to the overall crystal packing. In the fingerprint plot representing HÁ Á ÁH contacts, the 56.6% contribution to the overall crystal packing, is reflected by widely scattered points of high density due to the large hydrogen content of the molecule. The single spike in the centre at d e = d i = 0.936 Å in Fig. 5   importance of H-atom contacts in establishing the packing. The large number of HÁ Á ÁH, HÁ Á ÁC/CÁ Á ÁH, HÁ Á ÁO/OÁ Á ÁH, CÁ Á ÁC and HÁ Á ÁN/NÁ Á ÁH interactions suggest that van der Waals interactions and hydrogen bonding play the major roles in the crystal packing (Hathwar et al., 2015). A shape-index map of the title compound was generated in the range À1 to 1 Å (Fig. 3b). The convex blue regions on the shape-index symbolize hydrogen-donor groups and the concave red regions symbolize hydrogen-acceptor groups. The interactions on the shape-index map of the Hirshfeld surface are generally indicated by adjacent red and blue triangles.
A curvedness map of the title compound was generated in the range À4 to 0.4 Å (Fig. 3c). This shows large regions of green indicating a relatively flat surface area (planar), while the blue regions indicate areas of curvature. The presence of stacking interactions is also evident in the flat regions around the rings on the Hirshfeld surface plotted over curvedness (see the Supramolecular features section above).

4-(4-Methylbenzyl)-6-phenylpyridazin-3(2H)-one
Crystal data where P = (F o 2 + 2F c 2 )/3 (Δ/σ) max < 0.001 Δρ max = 0.30 e Å −3 Δρ min = −0.32 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 )