2-Oxo-2H-chromen-7-yl 4-methylbenzoate

Abstract

In the title compound, C 17 H 12 O 4 , the benzoate ring is oriented at an acute angle of 60.14 (13) relative to the coumarin plane (r.m.s. deviation = 0.006 Å ). This conformation is stabilized by an intramolecular C-HÁ Á ÁO weak hydrogen bond, which forms a five-membered ring. Also present are -stacking interactions between neighbouring pyrone and benzene rings [centroid-to-centroid distances in the range 3.6286 (1)-3.6459 (1) Å ] and C OÁ Á Á interactions [OÁ Á Ácentroid distances in the range 3.2938 (1)-3.6132 (1) Å ]. Hirshfeld surface analysis has been used to confirm and quantify the supramolecular interactions. Structure descriptionCoumarins and their derivatives constitute one of the major classes of naturally occurring compounds and interest in their chemistry continues unabated because of their usefulness as biologically active agents. They also form the core of several molecules of pharmaceutical importance. Coumarin and its derivatives have been reported to serve as anti-bacterial (Basanagouda et al., 2009), anti-oxidant (Vukovic et al., 2010 and antiinflammatory agents (Emmanuel-Giota et al., 2001). In view of their importance and as a continuation of our work on the crystal structure analysis of coumarin derivatives (Abou et al., 2012(Abou et al., , 2013, we report herein the synthesis, crystal structure and Hirshfeld surface analysis of the title compound.The molecular structure of the title compound is illustrated in Fig. 1. In this structure, an S(5) ring motif arises from an intramolecular C16-H16Á Á ÁO3 hydrogen bond IUCrData (2018). 3, x180927 data reports (Table 1), and generates a pseudo bicyclic ring system (Fig. 1). The coumarin ring system is planar [r.m.s. deviation = 0.006 Å ] and is oriented at an acute angle of 60.14 (13) with respect to the C11-C16 benzene ring, while the angles between the pseudo five-membered ring [r.m.s deviation = 0.007 Å ] and the coumarin ring system and C11-C16 benzene ring are 60.91 (12) and 1.06 (15) , respectively. These dihedral angles show that the five-membered hydrogen-bonded ring and the C11-C16 benzene ring are almost coplanar. Also, an inspection of the bond lengths shows that there is a slight asymmetry of the electron distribution around the pyrone ring: the C2-C3 [1.336 (5) Å ] and C1-C2 [1.446 (5) Å ] bond lengths are shorter and longer, respectively, than those excepted for a C ar -C ar bond. This feature suggests that the electron density is preferentially located on the C2-C3 bond of the pyrone ring, as seen in other coumarin derivatives (e.g. Gomes et al., 2016;Ziki et al., 2016).In the crystal, no intermolecular hydrogen bonds are observed. The unique close intermolecular contacts present are O2Á Á ÁH17A and C4Á Á ÁC1, with distances shorter than the sum of the van der Waals radii [O2Á Á ÁH17A(x, Ày, 1 2 + z) = 2.65 and C4Á Á ÁC1 (x, y À 1, z) = 3.364 (5) Å ], and unusual C1 O2Á Á Á interactions [O2Á Á ÁCg1 (x, 1 + y, z) = 3.294 (3), O2Á Á ÁCg4(x, 1 + y, z) = 3.613 (3) Å , where Cg1 and Cg4 are respectively the centroids of the pyrone ri...

Overview of Recent Advances in 3-Hydroxycoumarin Chemistry as a Bioactive Heterocyclic Compound

“…These types of compounds are usually in the form of crystals. This is the case for carboxylates of 4-hydroxycoumarin [40][41][42] and 7-hydroxycoumarin [43][44][45][46]. In the case of 3-hydroxycoumarin, the crystalline structure has been established for compounds 30b, 30c, 30d, 30e, 30g, 30j, 30h [6][7][47][48][49][50][51].…”