Crystal structure determination, Hirshfeld surface, crystal void, intermolecular interaction energy analyses, as well as DFT and energy framework calculations of 2-(4-oxo-4,5-dihydro-1H-pyrazolo-[3,4-d]pyrimidin-1-yl)acetic acid

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Irrou E., Elmachkouri Y. A., Oubella A., Ouchtak H., Dalbouha S., Mague J. T., ...Daha Fazla

ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, cilt.78, ss.953-964, 2022 (ESCI) identifier identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 78
  • Basım Tarihi: 2022
  • Doi Numarası: 10.1107/s2056989022008489
  • Dergi Adı: ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS
  • Derginin Tarandığı İndeksler: Emerging Sources Citation Index (ESCI), Scopus
  • Sayfa Sayıları: ss.953-964
  • Anahtar Kelimeler: crystal structure, hydrogen bond, C-H center dot center dot center dot pi(ring) interaction, pyrazolopyrimidine, QUANTITATIVE-ANALYSIS, MODEL ENERGIES, DERIVATIVES, CRYSTALEXPLORER, CONFORMATION, INHIBITORS, DESIGN
  • Hacettepe Üniversitesi Adresli: Evet

Özet

In the title molecule, C7H6N4O3, the bicyclic ring system is planar with the carboxymethyl group inclined by 81.05 (5)degrees to this plane. In the crystal, corrugated layers parallel to (010) are generated by N-H center dot center dot center dot O, O-H center dot center dot center dot N and C-H center dot center dot center dot O hydrogen-bonding interactions. The layers are associated through C-H center dot center dot center dot pi(ring) interactions. A Hirshfeld surface analysis indicates that the most important contributions to the crystal packing are from H center dot center dot center dot O/O center dot center dot center dot H (34.8%), H center dot center dot center dot N/N center dot center dot center dot H (19.3%) and H center dot center dot center dot H (18.1%) interactions. The volume of the crystal voids and the percentage of free space were calculated to be 176.30 angstrom(3) and 10.94%, showing that there is no large cavity in the crystal packing. Computational methods revealed O-H center dot center dot center dot N, N-H center dot center dot center dot O and C-H center dot center dot center dot O hydrogen-bonding energies of 76.3, 55.2, 32.8 and 19.1 kJ mol(-1), respectively. Evaluations of the electrostatic, dispersion and total energy frameworks indicate that the stabilization is dominated via dispersion energy contributions. Moreover, the optimized molecular structure, using density functional theory (DFT) at the B3LYP/6-311G(d,p) level, was compared with the experimentally determined one. The HOMO-LUMO energy gap was determined and the molecular electrostatic potential (MEP) surface was calculated at the B3LYP/6-31G level to predict sites for electrophilic and nucleophilic attacks.