Structures of Three Chalcones Derived from 6-Methoxy-2-naphthaldehyde |
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Authors: | Jerry P. Jasinski Ray J. Butcher Anil N. Mayekar H. S. Yathirajan B. Narayana |
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Affiliation: | (1) Department of Chemistry, Keene State College, 229 Main Street, Keene, NH 03435-2001, USA;(2) Department of Chemistry, Howard University, 525 College Street NW, Washington, DC 20059, USA;(3) Department of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore, 570 006, India;(4) Department of Studies in Chemistry, Mangalore University, Mangalagngotri, Mangalore, 574 199, India |
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Abstract: | Abstract In the molecular structures of three new structurally related chalcone derivatives, namely (2E)-1-(2-hydroxyphenyl)-3-(6-methoxy-2-naphthyl)prop-2-en-1-one, C20H16O3, I, (2E)-1-(2-chloropyridin-4-yl)-3-(6-methoxy-2-naphthyl)prop-2-en-1-one, C19H14ClNO2, II, and (2E)-3-(6-methoxy-2-naphthyl)-1-pyridin-4-ylprop-2-en-1-one, III, C19H15NO2, the configuration of the keto group is syn with respect to the olefinic double bond. In all three structures the molecules pack with weak intermolecular C–H···O interactions utilizing both the methoxy and keto oxygen’s in I, the methoxy oxygen in II and the keto oxygen in III. These interactions link the molecules into chains diagonally along the (011) plane of the unit cell in I and III and along the (010) plane in II. The dihedral angle between the phenyl and 2-napthyl rings in I is 31.7(3)°. In II and III the dihedral angle between the pyridyl and 2-naphthyl rings is 14.4(9)° and 1.8(9)°, respectively. C–H···O hydrogen bonding interactions influence these twist angles of these rings in I–III while weak π–π stacking interactions between naphthyl rings in I and III and also between pyridyl and naphthyl rings in II help stabilize crystal packing. [I: P2 1 /c, a = 7.6635(4) ?, b = 11.8047(6) ?, c = 16.7584(7) ?, β = 99.271(5)°, V = 1496.25(13) ?3; II: Pbca, a = 14.1424(4) ?, b = 6.0957(2) ?, c = 33.1458(11) ?, V = 2857.43(16) ?3; III: P2 1 /c, a = 11.5155(4) ?, b = 6.0020(2) ?, c = 22.4645(8) ?, β = 103.002(4)°, V = 1512.85(9) ?3]. Index Abstract Crystal structures from three Chalcones derived from 6-methoxy-2-naphthaldehyde are reported and their geometric and packing parameters described. |
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Keywords: | Chalcones Crystal structure Hydrogen bonds Naphthyl Pyridyl Phenyl Syn Trans |
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