2-[(2,4,6-Trimethylbenzene)sulfonyl]phthalazin-1(2H)-one: crystal structure, Hirshfeld surface analysis and computational study

Izuogu, D. C. and Asegbeloyin, J. N. and Jotani, Mukesh M. and Tiekink, Edward R. T. * (2020) 2-[(2,4,6-Trimethylbenzene)sulfonyl]phthalazin-1(2H)-one: crystal structure, Hirshfeld surface analysis and computational study. Acta Crystallographica Section E Crystallographic Communications, 76 (5). pp. 697-702. ISSN 2056-9890

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Abstract

The X-ray crystal structure of the title phthalazin-1-one derivative, C17H16N2O3S {systematic name: 2-[(2,4,6-tri­methyl­benzene)­sulfon­yl]-1,2-di­hydro­phthalazin-1-one}, features a tetra­hedral sulfoxide-S atom, connected to phthalazin-1-one and mesityl residues. The dihedral angle [83.26 (4)°] between the organic substituents is consistent with the mol­ecule having the shape of the letter V. In the crystal, phthalazinone-C6-C—H...O(sulfoxide) and π(phthalazinone-N2C4)–π(phthalazinone-C6) stacking [inter-centroid distance = 3.5474 (9) Å] contacts lead to a linear supra­molecular tape along the a-axis direction; tapes assemble without directional inter­actions between them. The analysis of the calculated Hirshfeld surfaces confirm the importance of the C—H...O and π-stacking inter­actions but, also H...H and C—H...C contacts. The calculation of the inter­action energies indicate the importance of dispersion terms with the greatest energies calculated for the C—H...O and π-stacking inter­actions.

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