Abstract
In the title compound, C15H12N2O3, pairs of mol-ecules are linked into dimers by N-H⋯O hydrogen bonds, forming an R 2 2(12) ring motif, with the dimers stacked along the a axis. These dimers are connected through π-π stacking inter-actions between the centroids of the benzene and furan rings of their 2,3-di-hydro-1-benzo-furan ring systems. Furthermore, there exists a C-H⋯π inter-action that consolidates the crystal packing. A Hirshfeld surface analysis indicates that the most important contacts are H⋯H (40.7%), O⋯H/H⋯O (24.7%), C⋯H/H⋯C (16.1%) and C⋯C (8.8%).
Highlights
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)
These dimers are stacked along the a axis and connected by – stacking interactions between the centroids of the benzene and furan rings of their 2,3-dihydro1-benzofuran ring systems [Cg1Á Á ÁCg2(1 À x, À y, 1 À z) = 3.5316 (19) A, slippage = 0.352 A, where Cg1 and Cg2 are the centroids of the benzene (C3–C8) and furan (O1/C1–C3/C8) rings, respectively] (Figs. 2, 3 and 4)
Structural commentary In the title compound, the molecular conformation is stabilized by an intramolecular N2—H1Á Á ÁO2 hydrogen bond, forming an S(6) ring motif (Table 1, Fig. 1; Bernstein et al, 1995)
Summary
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). 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, 2021; Mahmudov 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). There exists a C—HÁ Á Á interaction between the H9C atom of the methyl group C9 and the centroid of the phenyl ring (C10–C15)
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