Crystal structure and Hirshfeld surface analysis of (E)-N-[(2-ethoxynaphthalen-1-yl)methylidene]-5,6,7,8-tetrahydronaphthalen-1-amine

The two ring systems are twisted by 51.40 (11)°. In the crystal, the molecules are linked via C—H⋯π interactions, forming a three-dimensional framework.


Chemical context
Schiff bases have found wide use as a ligands in coordination chemistry (Calligaris et al., 1972;Hö kelek et al., 2004;Moroz et al., 2012) and are also important in various areas of chemistry and biochemistry because of their biological activity (El-masry et al., 2000). Many Schiff bases have some antibacterial, anticancer and antioxidant properties and have therefore been used as starting materials in the synthesis of important medicinal substances. In the present study, we designed a new type of Schiff base obtained by the reaction of 2-ethoxy-1naphthaldehyde and 5,6,7,8-tetrahydro-1-naphtylamine to give (E)-N-[(2-ethoxynaphthalen-1-yl)methylene]-5,6,7,8tetrahydronaphthalen-1-amine. We report herein the synthesis, crystal structure and Hirshfeld structural analysis of the title compound.

Supramolecular features
In the crystal, the molecules are connected by C-HÁ Á Á interactions, generating a three-dimensional supramolecular structure (Table 1 and Fig. 2).

Hirshfeld surface analysis
Hirshfield surface analysis was performed using Crystal-Explorer (Turner et al., 2017). The Hirshfeld surfaces and their associated two-dimensional fingerprint plots were used to quantify the various intermolecular interactions. The Hirsh- The molecular structure of the title compound, showing the atom labelling. Displacement ellipsoids are drawn at the 20% probability level. Table 1 Hydrogen-bond geometry (Å , ).
Cg1 and Cg2 are the centroids of the C5-C10 and C14-C23 rings.
A view of the three-dimensional Hirshfeld surface of the title compound plotted over electrostatic potential energy in the range À0.048 to 0.033 a.u. using the STO-3G basis set at the Hartree-Fock level of theory is shown in Fig. 6; the donors and acceptors are shown as blue and red areas around the atoms related with positive (hydrogen-bond donors) and

Figure 6
A view of the three-dimensional Hirshfeld surface plotted over electrostatic potential energy.

Figure 3
The Hirshfeld surface of the title compound mapped over d norm .

(E)-N-[(2-Ethoxynaphthalen-1-yl)methylidene]-5,6,7,8-tetrahydronaphthalen-1-amine
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.