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. 2020 Apr 3;76(Pt 5):605-610.
doi: 10.1107/S2056989020004284. eCollection 2020 May 1.

Crystal structure, Hirshfeld surface analysis and inter-action energy and DFT studies of 2-(2,3-di-hydro-1 H-perimidin-2-yl)-6-meth-oxy-phenol

Ballo Daouda  1   2 , Nanou Tiéba Tuo  2 , Tuncer Hökelek  3 , Kangah Niameke Jean-Baptiste  4 , Kodjo Charles Guillaume  5 , Kablan Ahmont Landry Claude  6 , El Mokhtar Essassi  1
Affiliations

Crystal structure, Hirshfeld surface analysis and inter-action energy and DFT studies of 2-(2,3-di-hydro-1 H-perimidin-2-yl)-6-meth-oxy-phenol

Ballo Daouda et al. Acta Crystallogr E Crystallogr Commun. .

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.

Keywords: Hirshfeld surface; crystal structure; meth­oxy­phenol; perimidin.

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Figures

Figure 1
Figure 1
The asymmetric unit of the title compound with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.
Figure 2
Figure 2
A partial packing diagram viewed along the a-axis direction with O—HPhnl⋯NPrmdn and N—HPrmdn⋯OPhnl (Phnl = phenol and Prmdn = perimidine) hydrogen bonds shown as dashed lines. H-atoms not included in hydrogen bonding have been omitted for clarity.
Figure 3
Figure 3
View of the three-dimensional Hirshfeld surface of the title compound plotted over d norm in the range −0.4133 to 1.3883 a.u.
Figure 4
Figure 4
View of the three-dimensional Hirshfeld surface of the title compound plotted over electrostatic potential energy in the range −0.0500 to 0.0500 a.u. using the STO-3 G basis set at the Hartree–Fock level of theory. Hydrogen-bond donors and acceptors are shown as blue and red regions around the atoms corresponding to positive and negative potentials, respectively.
Figure 5
Figure 5
Hirshfeld surface of the title compound plotted over shape-index.
Figure 6
Figure 6
The full two-dimensional fingerprint plots for the title compound, showing (a) all inter­actions, and delineated into (b) H⋯H, (c) H⋯C/C⋯H, (d) H⋯O/O⋯H, (e) H⋯N/N⋯H and (f) O⋯C/C⋯O inter­actions. The d i and d e values are the closest inter­nal and external distances (in Å) from given points on the Hirshfeld surface contacts.
Figure 7
Figure 7
The Hirshfeld surface representations with the function d norm plotted onto the surface for (a) H⋯H, (b) H⋯C/C⋯H and (c) H⋯O/O⋯H inter­actions.
Figure 8
Figure 8
The energy band gap of the title compound, (I).
See this image and copyright information in PMC

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