The crystal structure of the title compound, C18H17FO4, reported here is a polymorph of the structure first reported by Patil et al.[Mol.Cryst.Liq.Cryst.
Sci.Technol.Sect.A (2007), 461, 123–130].It is a chalcone analog and consists of substituted phenyl rings bonded at the opposite ends of a propenone group, the biologically active region.
The dihedral angle between the mean planes of the aromatic rings within the 4-fluorophenyl and trimethoxyphenyl groups is 28.7 (1)° compared to 20.8 (6)° in the published structure.The angles between the mean plane of the prop-2-ene-1-one group and the mean plane of product aromatic rings within the 4-fluorophenyl and trimethoxyphenyl groups are 30.3 (4) and 7.
4 (7)°, respectively, in contast to 10.7 (3) and 12.36° for the polymorph.While the two 3-methoxy groups are in the plane of the trimethoxy-substituted ring, the 4-methoxy group is in a synclinical [−sc = −78.1 (2)°] or anticlinical [+ac = 104.
0 (4)°] position, compared to a +sc [53.0 (4)°] or −ac [−132.4 (7)°] position.While no classical hydrogen bonds are present, weak intermolecular C—H.π-ring interactions are observed which contribute to the stability of the crystal packing.
The two polymorphs crystallize in the same space group, P21/c, opi the color that keeps on giving but have different cell parameters for the a, b and c axes and the β angle.A comparison of the molecular geometries of both polymorphs to a geometry optimized density functional theory (DFT) calculation at the B3-LYP/6–311+G(d,p) level for each structure provides additional support to these observations.