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Crystals 2012, 2(3), 1239-1247; doi:10.3390/cryst2031239
Article

Crystal and Molecular Structure Studies of Ethyl 4-(4-Hydroxyphenyl)-6-(6-methoxy-2-naphthyl)-2-oxocyclohex-3-ene-1-carboxylate and Ethyl 4-(3-Bromophenyl)-6-(6-methoxy-2-naphthyl)-2-oxocyclohex-3-ene-1-carboxylate

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Received: 24 July 2012 / Revised: 8 August 2012 / Accepted: 15 August 2012 / Published: 27 August 2012
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Abstract

The crystal and molecular structures of the title compounds, ethyl 4-(4-hydroxyphenyl)-6-(6-methoxy-2-naphthyl)-2-oxocyclohex-3-ene-1-carboxylate (I) and ethyl 4-(3-bromophenyl)-6-(6-methoxy-2-naphthyl)-2-oxocyclohex-3-ene-1-carboxylate (II), are reported and confirmed by single crystal X-ray diffraction data. Compound (I), C26H24O5, crystallizes from a methanol solution in the monoclinic C2/c space group with eight molecules in the unit cell. The unit cell parameters are: a = 25.4114(5) Å, b = 8.47440(10) Å, c = 20.6921(4) Å, β = 108.328(2)° and V = 4229.92(13) Å3. Disorder is observed throughout the entire molecule with an occupancy ratio 0.690(2):0.310(2). Compound (II), C26H23O4Br, crystallizes from an ethyl acetate solution in the monoclinic P21/c spacegroup with four molecules in the unit cell. The unit cell parameters are a = 17.8991(9) Å, b = 11.4369(6) Å, c = 10.8507(5) Å, β = 92.428(4)° and V = 2219.25(19) Å3. Disorder is observed in the cyclohexenone ring and the carboxylate group with an occupancy ratio 0.830(6):0.170(6). Weak O–H...O (I) or C–H...O (II) intermolecular interactions are observed which influence crystal packing stability. These chalcone derivative types of molecules are important in their ability to act as activated unsaturated systems in conjugated addition reactions of carbanions in the presence of basic catalysts which exhibit a multitude of biological activities.
Keywords: cyclohexenecarboxylates; X-ray crystal structure; disorder; weak intermolecular interactions cyclohexenecarboxylates; X-ray crystal structure; disorder; weak intermolecular interactions
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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Kaur, M.; Jasinski, J.P.; Butcher, R.J.; Yathirajan, H.S.; Mayekar, A.N.; Narayana, B. Crystal and Molecular Structure Studies of Ethyl 4-(4-Hydroxyphenyl)-6-(6-methoxy-2-naphthyl)-2-oxocyclohex-3-ene-1-carboxylate and Ethyl 4-(3-Bromophenyl)-6-(6-methoxy-2-naphthyl)-2-oxocyclohex-3-ene-1-carboxylate. Crystals 2012, 2, 1239-1247.

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