Crystal structure and Hirshfeld surface analysis of (3Z)-7-methoxy-3-(2-phenylhydrazinylidene)-1-benzofuran-2(3H)-one

Pairs of molecules in the crystal are linked into dimers by N—H⋯O hydrogen bonds, forming an (12) ring motif. The dimers are connected through π–π stacking interactions between the centroids of the benzene and furan rings of their 2,3-dihydro-1-benzofuran ring systems. C—H⋯π interactions consolidate the crystal packing.


Chemical context
Hydrazones are a versatile class of organic ligands that have extensive applications in synthetic transformations, the synthesis of bioactive compounds, the design of materials and in coordination chemistry (Ma et al., 2017a,b;Viswanathan et al., 2019). Moreover, metal complexes of hydrazone ligands have been successfully applied as catalysts in organic synthesis . The properties of metal-hydrazonates can be regulated by the design of ligands through the involvement of non-covalent-bond donor or acceptor substituents (Ma et al., 2020(Ma et al., , 2021Mahmudov et al., 2013). Supramolecular networks of all dimensions in the crystal structures of hydrazone compounds or metal-hydrazonates, resulting from extensive hydrogen-bonding and other types of intermolecular interactions, have been reported (Gurbanov et al., 2020a;Kopylovich et al., 2011). Thus, the attachment of suitable substituents or synthons to hydrazone ligands can improve their functional properties and the catalytic or biological activity of the corresponding coordination compounds (Mizar et al., 2012;Gurbanov et al., 2020a,b;Khalilov et al., 2018a,b;Maharramov et al., 2018;Shihkaliyev et al., 2019;Shixaliyev et al., 2014). ISSN 2056-9890 In a continuation of our work in this context (Atiog lu et al., 2020, we have synthesized a new hydrazone compound, (3Z)-7-methoxy-3-(2-phenylhydrazinylidene)-1-benzofuran-2(3H)-one, which shows multiple intermolecular non-covalent interactions.

Figure 3
A view of the molecular packing of the title compound along the a-axis direction. Intermolecular interactions are depicted as in Fig. 2.

Figure 1
The title molecule with the labelling scheme and displacement ellipsoids drawn at the 30% probability level. The intramolecular N-HÁ Á ÁO hydrogen bond is shown as a dashed line.

Hirshfeld surface analysis
Crystal Explorer 17.5 (Turner et al., 2017) was used to calculate the Hirshfeld surfaces and generate the two-dimensional fingerprint plots. Hirshfeld surfaces allow for the display of intermolecular interactions by using distinct colours and intensities to indicate short and long contacts, as well as the relative strength of the interactions. The three-dimensional Hirshfeld surface of the title compound plotted over d norm in the range À0.1718 to 1.3843 a.u. is shown in Fig. 5. The N2-H1Á Á ÁO2 interactions, which play a key role in the molecular packing of the title compound, are responsible for the red spot that occurs around O2. The bright-red spots appearing near O2 and hydrogen atom H1 indicate their roles as donors and/ or acceptors in hydrogen-bonding; they also appear as blue and red regions corresponding to positive and negative potentials on the Hirshfeld surface mapped over electrostatic potential (Spackman et al., 2008) shown in Fig. 6. Here the blue regions indicate positive electrostatic potential (hydrogen-bond donors), while the red regions indicate negative electrostatic potential (hydrogen-bond acceptors). The overall two-dimensional fingerprint plot for the title compound is given in Fig. 7a, and those delineated into HÁ Á ÁH, OÁ Á ÁH/HÁ Á ÁO, CÁ Á ÁH/HÁ Á ÁC and CÁ Á ÁC contacts are shown in Fig. 7b-e, while numerical details of the different contacts are given in Table 2 View of the three-dimensional Hirshfeld surface of the title compound plotted over d norm in the range À0.1718 to 1.3843 a.u. The two N-HÁ Á ÁO hydrogen bonds forming the dimer are depicted as dashed lines.

Figure 4
A view of the molecular packing of the title compound along the b-axis direction. Intermolecular interactions are depicted as in Fig. 2.

Figure 6
View of the three-dimensional Hirshfeld surface of the title compound plotted over electrostatic potential energy in the range À0.0500 to 0.0500 a.u. using the STO-3 G basis set at the Hartree-Fock level of theory. The hydrogen-bond donors and acceptors are viewed as blue and red regions, respectively, around atoms, corresponding to positive and negative potentials. Table 2 Interatomic contacts of the title compound (Å ).

Contact
Distance Symmetry operation 3.07 1 2 À x, À 1 2 + y, 3 2 À z TODMEH and TODMOR crystallize in the monoclinic space group P2 1 /c with Z = 4. TODMIL crystallizes in the monoclinic space group I2/a with Z = 8 and TODMUX crystallizes in the triclinic space group P1 with Z = 2. EXIWOA crystallizes in the monoclinic space group P2 1 /c with Z = 4. The E conformation in TODMEH, TODMIL and TODMUX is stabilized by a strong intermolecular N-HÁ Á ÁO interaction. These interactions lead to the formation of dimeric structural arrangements. In the crystal packing of TODMOR, an intermolecular N-HÁ Á ÁN interaction results in a zigzag structural arrangement, with the formation of chains along the crystallographic b axis. Non-classical intermolecular C-HÁ Á ÁN and C-HÁ Á ÁO interactions are also observed in the crystal structures of TODMEH, TODMIL, TODMOR and TODMUX. In EXIWOA, molecules are linked by C-HÁ Á Á, C-ClÁ Á Á, ClÁ Á ÁCl and ClÁ Á ÁH interactions, forming a three-dimensional supramolecular network.

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 )