Abstract
The title compound, C18H16N2O2, consists of perimidine and meth-oxy-phenol units, where the tricyclic perimidine unit contains a naphthalene ring system and a non-planar C4N2 ring adopting an envelope conformation with the NCN group hinged by 47.44 (7)° with respect to the best plane of the other five atoms. In the crystal, O-HPhnl⋯NPrmdn and N-HPrmdn⋯OPhnl (Phnl = phenol and Prmdn = perimidine) hydrogen bonds link the mol-ecules into infinite chains along the b-axis direction. Weak C-H⋯π inter-actions may further stabilize the crystal structure. The Hirshfeld surface analysis of the crystal structure indicates that the most important contributions for the crystal packing are from H⋯H (49.0%), H⋯C/C⋯H (35.8%) and H⋯O/O⋯H (12.0%) inter-actions. Hydrogen bonding and van der Waals inter-actions are the dominant inter-actions in the crystal packing. Computational chemistry indicates that in the crystal, the O-HPhnl⋯NPrmdn and N-HPrmdn⋯OPhnl hydrogen-bond energies are 58.4 and 38.0 kJ mol-1, respectively. Density functional theory (DFT) optimized structures at the B3LYP/ 6-311 G(d,p) level are compared with the experimentally determined mol-ecular structure in the solid state. The HOMO-LUMO behaviour was elucidated to determine the energy gap.
Highlights
In the crystal, O—HPhnlÁ Á ÁNPrmdn and N—HPrmdnÁ Á ÁOPhnl (Phnl = phenol and Prmdn = perimidine) hydrogen bonds (Table 1) link the molecules into infinite chains along the baxis direction (Fig. 2)
We report the synthesis, the molecular and crystal structures along with Hirshfeld surface analysis and computational calculations of the title compound, (I)
In order to visualize the intermolecular interactions in the crystal of the title compound, a Hirshfeld surface (HS) analysis (Hirshfeld, 1977; Spackman & Jayatilaka, 2009) was carried out by using Crystal Explorer 17.5 (Turner et al, 2017)
Summary
Six-membered heterocyclic compounds carrying two nitrogen atoms have been widely studied (Aly & El-Shaieb, 2004; Koca et al, 2012; Zhao et al, 2012; Baranov & Fadeev, 2016; Lahmidi et al, 2018). Perimidine derivatives (perinaphtho-fused perimidine ring systems) in particular have aroused a lot of interest because of their applications in photophysics (Del Valle et al, 1997) and their use as colouring matters for polyester fibers (Claramunt et al, 1995) and as fluorescent materials (Varsha et al, 2010). These molecules have a wide range of biological applications (Dzieduszycka et al, 2002), indicating that the perimidine group is a potentially useful model in medicinal chemistry research and therapeutic applications.
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