Abstract
The reaction between 5-fluoro-isatin and hydroxyl-amine hydro-chloride in acidic ethanol yields the title compound, C8H5FN2O2, whose mol-ecular structure matches the asymmetric unit and is nearly planar with an r.m.s. deviation for the mean plane through all non-H atoms of 0.0363 Å. In the crystal, the mol-ecules are linked by N-H⋯N, N-H⋯O and O-H⋯O hydrogen-bonding inter-actions into a two-dimensional network along the (100) plane, forming rings with R22 (8) and R12 (5) graph-set motifs. The crystal packing also features weak π-π inter-actions along the [100] direction [centroid-to-centroid distance 3.9860 (5) Å]. Additionally, the Hirshfeld surface analysis indicates that the major contributions for the crystal structure are the O⋯H (28.50%) and H⋯F (16.40%) inter-actions. An in silico evaluation of the title compound with the vascular endothelial growth factor receptor-2 (VEGFR-2) was carried out. The title compound and the selected biological target VEGFR-2 show the N-H⋯O(GLU94), (CYS96)N-H⋯O(isatine) and (PHE95)N-H⋯O(isatine) inter-molecular inter-actions, which suggests a solid theoretical structure-activity relationship.
Highlights
Crystal structure, Hirshfeld analysis and molecular docking with the vascular endothelial growth factor receptor-2 of (3Z)-5-fluoro-3-(hydroxyimino)indolin-2-one
The molecules are linked by N—HÁ Á ÁN, N—HÁ Á ÁO and O—HÁ Á ÁO hydrogen-bonding interactions into a two-dimensional network along the (100) plane, forming rings with R22(8) and R12(5) graph-set motifs
The Hirshfeld surface analysis indicates that the major contributions for the crystal structure are the OÁ Á ÁH (28.50%) and HÁ Á ÁF (16.40%) interactions
Summary
The chemistry of isatin is already well documented due to its wide range of applications, especially in organic synthetic chemistry and medicinal chemistry. Two recent examples of this are the synthesis of 1-[(2-methylbenzimidazol-1-yl) methyl]-2-oxo-indolin-3-ylidene]amino]thiourea, an in vitro and in silico Chikungunya virus inhibitor (Mishra et al, 2016) and 5-chloroisatin-4-methylthiosemicarbazone, an intermediate in the HIV-1 (human immunodeficiency virus type 1) RT (reverse transcriptase) inhibitor (Meleddu et al, 2017). For these reasons, the crystal structure determination of isatin-based molecules is an intensive research field and one of our major research aims. Symmetry codes: (i) Àx þ 1; Ày þ 2; Àz þ 1; (ii) Àx þ 1; y À 12; Àz þ 32
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