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A second polymorph of (2E)-1-(4-fluorophenyl)-3-(3,4,5-trimethoxyphenyl)prop-2-en-1-one

Acta Crystallographica Section E

Structure Reports Online

Volume 65, Part 8 (August 2009)


organic compounds



sj2632 scheme

Acta Cryst. (2009). E65, o1965-o1966    [ doi:10.1107/S1600536809028517 ]

A second polymorph of (2E)-1-(4-fluorophenyl)-3-(3,4,5-trimethoxyphenyl)prop-2-en-1-one

J. P. Jasinski, R. J. Butcher, K. Veena, B. Narayana and H. S. Yathirajan

Abstract: 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 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...[pi]-ring interactions are observed which contribute to the stability of the crystal packing. The two polymorphs crystallize in the same space group, P21/c, but have different cell parameters for the a, b and c axes and the [beta] 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.

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