3-(3-Fluorobenzyl)-1H-isochromen-1-one

Abstract

The asymmetric unit of the title compound, C16H11FO2, contains two independent mol­ecules. The isochromene ring systems are planar and are oriented with respect to the fluoro­benzene rings at dihedral angles of 87.15 (3) and 87.85 (3)° in the two mol­ecules.

Crystal structure and Hirshfeld surface analysis of 2-[(2-oxo-2H-chromen-4-yl)oxy]acetic acid dimethyl sulfoxide monosolvate

“…Many of these compounds have proven to be active as antibacterial, antifungal, anti-inflammatory, anticoagulant, anti-HIV and antitumor agents Govindhan, Subramanian, Sridharan et al, 2015). Sulfur-containing isocoumarins (Henderson & Hill, 1982), fluorine-containing isocoumarins (Babar et al, 2008) and chlorine-containing isocoumarins (Abid et al, 2008) have also been studied. In view of the importance of their natural occurrence, biological, pharmacological and medicinal activities, and their use as synthetic intermediates, we have synthesized the title derivative 2-[(2oxo-2H-chromen-4-yl)oxy]acetic acid dimethyl sulfoxide monosolvate, and report herein on its crystal structure and Hirshfeld surface analysis.…”

3-(3-Bromobenzyl)-1H-isochromen-1-one

“…For the properties and applications of isocoumarins and 3,4dihydroisocoumarins, see: Chinworrungsee et al (2002); Devienne et al (2002); Mali & Babu (1998); Rama et al (1998); Waters & Kozlowski (2001). For related structures, see: Abid et al (2008); Babar et al (2008).…”

“…In view of the importance of this class of compounds, the title compound, an isocoumarine derivative containing a 3-bromobenzyl substituent, has been synthesized and its crystal structure is reported here. We have previously reported the structures of the analogous fluorine and chlorine derivatives (Babar et al, 2008;Abid et al, 2008), which crystallize with two and three molecules respectively in the asymmetric unit.…”

“…The structure is not isotypic to either of the analogous derivatives. Bond lengths and angles may be regarded as normal by comparison with the earlier structures (Babar et al, 2008;Abid et al, 2008) The packing diagram (Fig. 2) shows the molecules to be linked by two C-H•••O hydrogen bonds (Table 1) and by π-π stacking interactions between the coumarin units and between the bromobenzene rings, with centroid-to-centroid distances ranging from 3.667 (2) to 3.765 2…”