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. 2020 May 5;76(Pt 6):798-802.
doi: 10.1107/S2056989020005939. eCollection 2020 Jun 1.

Crystal structure, Hirshfeld surface analysis and DFT studies of 2-(2,3-di-hydro-1 H-perimidin-2-yl)phenol

Ballo Daouda  1   2 , Nanou Tiéba Tuo  3 , Niameke Jean-Baptiste Kangah  3 , Tuncer Hökelek  4 , Charles Guillaume Kodjo  3 , Pascal Retailleau  5 , El Mokhtar Essassi  1
Affiliations

Crystal structure, Hirshfeld surface analysis and DFT studies of 2-(2,3-di-hydro-1 H-perimidin-2-yl)phenol

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

Abstract

The asymmetric unit of the title compound, C17H14N2O, contains two independent mol-ecules each consisting of perimidine and phenol units. The tricyclic perimidine units contain naphthalene ring systems and non-planar C4N2 rings adopting envelope conformations with the C atoms of the NCN groups hinged by 44.11 (7) and 48.50 (6)° with respect to the best planes of the other five atoms. Intra-molecular O-H⋯N hydrogen bonds may help to consolidate the mol-ecular conformations. The two independent mol-ecules are linked through an N-H⋯O hydrogen bond. The Hirshfeld surface analysis of the crystal structure indicates that the most important contributions for the crystal packing are from H⋯H (52.9%) and H⋯C/C⋯H (39.5%) inter-actions. Hydrogen bonding and van der Waals inter-actions are the dominant inter-actions in the crystal packing. 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; perimidine; phenol.

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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
View of the three-dimensional Hirshfeld surface of the title compound plotted over d norm in the range −0.1813 to 1.6330 a.u.
Figure 3
Figure 3
Hirshfeld surface of the title compound plotted over shape-index.
Figure 4
Figure 4
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 5
Figure 5
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 6
Figure 6
The energy band gap of the title compound.
See this image and copyright information in PMC

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