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

Manpreet Kaur 1 email, Jerry P. Jasinski 2,* email, Ray J. Butcher 3 email, Hemmige S. Yathirajan 1 email, Anil N. Mayekar 4 email and Badiadka Narayana 5 email
1 Department of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore-570 006, India 2 Department of Chemistry, Keene State College, 229 Main Street, Keene, NH 03435, USA 3 Department of Chemistry, Howard University, 525 College Street NW, Washington DC 20059, USA 4 SeQuent Scientific Limited, Baikampady, Mangalore-575 011, India 5 Department of Studies in Chemistry, Mangalore University, Mangalagangotri-574 199, India
* Author to whom correspondence should be addressed.
Received: 24 July 2012; in revised form: 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

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MDPI and ACS Style

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.

AMA Style

Kaur M, Jasinski JP, Butcher RJ, Yathirajan HS, Mayekar AN, 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(3):1239-1247.

Chicago/Turabian Style

Kaur, Manpreet; Jasinski, Jerry P.; Butcher, Ray J.; Yathirajan, Hemmige S.; Mayekar, Anil N.; Narayana, Badiadka. 2012. "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 2, no. 3: 1239-1247.

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