3-Benzylidene-6-methoxychroman-4-one

Abstract

In the title compound, C17H14O3, the dihedral angle between the phenyl ring and the benzene ring of the chromanone moiety is 67.78 (3)°. The six-membered heterocyclic ring of the chromanone moiety adopts a half-chair conformation. The structure is stabilized by weak inter­molecular C—H⋯O inter­actions that link the mol­ecules into inversion dimers.

Structural studies of seven homoisoflavonoids, six thiohomoisoflavonoids, and four structurally related compounds

“…The dihedral angle C8a-O1-C2-C3 (Fig. 1, Table 4) is rather close to ±50°in all molecules of IIIa-IIId and have rather similar angle values in previously known derivatives (38°-54°) [35][36][37][38][39][40][41][42][43][44]. The positive or negative angles show that C2 is on the left (?)…”

“…In IIIb-IIId these values are slightly smaller (46°-55°) as also in several 3-benzylidene-4-chromanone derivatives [37,38,[40][41][42][43][44]. 3-Benzylidene-6-methoxychroman-4-one [36] shows value of 67.78(3)°f or this angle and is the only one significantly larger. Carbon C2 is on the same side of the C4a-C8a-plane as C2 0 in all 3-benzylidene-4-chromanone derivatives.…”

“…Small static disorder was found to occur in the case of C3 and C2a, but the solving of it was not successful without using strong positional and anisotropic constraints and it was not resolved in the least squares refinement. The angle between the planes of two aromatic rings (Table 5) is smaller than in V but larger than in IIIa-IIId and most of the related 3-benzylidene-4-chromanone structures [35][36][37][38][39][40][41][42][43][44]. Three known 2-benzyl-1-tetralone derivatives [48][49][50] show larger inclination angles (74°-80°) between aromatic planes, but slightly smaller twist of the molecule end, according to C8a-C1-C2-C2a dihedral angles (162°-168°).…”

“…The crystal structure of (E)-3-benzylidene-4-chromanone was published in 1987 by Katrusiak et al [35] and our structural search showed that since then nine substituted derivatives [36][37][38][39][40][41][42][43][44] of it have been added to Cambridge Structural Database (CSD) [45]. The crystallographic diagrams for four new derivatives IIIa-IIId are presented in Fig.…”

3-(3-Methoxybenzylidene)chroman-4-one

“…For the preparation, see: Shaikh et al (2011). For related structures, see: Kirkiacharian et al (1984); Marx et al (2008); Suresh et al (2007); Chantrapromma et al (2006); Augustine et al (2008). For the biological activity of this class of compound, see: du Toit et al (2010).…”