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

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.

SUBMITTER: Daouda B

PROVIDER: S-EPMC7273993 | biostudies-literature |

REPOSITORIES: biostudies-literature

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

Project description: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?? 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.

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Project description:The title compound, C15H14ClNO, was synthesized by condensation reaction of 2-hy-droxy-5-methyl-benzaldehyde and 3-chloro-4-methyl-aniline, and crystallizes in the monoclinic space group P21/c. The 3-chloro-benzene ring is inclined to the phenol ring by 9.38?(11)°. The configuration about the C=N bond is E and an intra-molecular O-H?N hydrogen bond forms an S(6) ring motif. The Hirshfeld surface analysis of the crystal structure indicates that the most important contributions for the packing arrangement are from H?H (43.8%) and C?H/H?C (26.7%) inter-actions. The density functional theory (DFT) optimized structure at the B3LYP/ 6-311?G(d,p) level is compared with the experimentally determined mol-ecular structure and the HOMO-LUMO energy gap is provided.

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