Structures of Three Chalcones Derived from 6-Methoxy-2-naphthaldehyde
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) Å, b = 11.8047(6) Å, c = 16.7584(7) Å, β = 99.271(5)°, V = 1496.25(13) Å3; II: Pbca, a = 14.1424(4) Å, b = 6.0957(2) Å, c = 33.1458(11) Å, V = 2857.43(16) Å3; III: P2 1 /c, a = 11.5155(4) Å, b = 6.0020(2) Å, c = 22.4645(8) Å, β = 103.002(4)°, V = 1512.85(9) Å3].
Crystal structures from three Chalcones derived from 6-methoxy-2-naphthaldehyde are reported and their geometric and packing parameters described. Open image in new window
KeywordsChalcones Crystal structure Hydrogen bonds Naphthyl Pyridyl Phenyl Syn Trans
ANM thanks University of Mysore for use of their research facilities. RJB acknowledges the NSF MRI program (grant No. CHE-0619278) for funds to purchase the X-ray diffractometer.
- 1.Dimmock JR, Elias DW, Beazely MA, Kandepu NM (1999) Curr Med Chem 6:1125–1149Google Scholar
- 5.Go ML, Wu X, Liu XL (2005) Curr Med Chem 12:483–499Google Scholar
- 6.Oxford Diffraction, CrysAlisPro (Version 171.31.8) and CrysAlis RED (Version 220.127.116.11). Oxford Diffraction Ltd., Abingdon, Oxfordshire, England, 2007Google Scholar
- 7.Sheldrick GM (1997) SHELXS97 and SHELXL97. University of Göttingen, GermanyGoogle Scholar
- 8.Bruker SHELXTL. Version 6.10 (2000) Bruker AXS Inc., Madison, Wisconsin, USAGoogle Scholar
- 11.Yathirajan HS, Narayana B, Ashalatha BV, Sarojini BK, Bolte M (2006) Acta Cryst E62:o4440–o4441Google Scholar
- 12.Yathirajan HS, Mayekar AN, Sarojini BK, Narayana B, Bolte M (2007) Acta Cryst E63:o1012–o1013Google Scholar
- 13.Yathirajan HS, Mayekar AN, Sarojini BK, Narayana B, Bolte M (2007a) Acta Cryst E63:o1140–o1141Google Scholar
- 14.Butcher RJ, Yathirajan HS, Ashalatha BV, Narayana B, Sarojini BK (2007) Acta Cryst E63:o1430–o1431Google Scholar
- 15.Stewart JJ (1990) MOPAC, A General Molecular Orbital Package, Frank J. Seiler Research Lab, United States Air Force Academy, No. ADA233489Google Scholar
- 16.Schmidt JR, Polik WF (2007) WebMO Pro, version 8.0.010e; WebMO, LLC, Holland, MI, USA.Eur J. Med. Chem. Available from http://www.webmo.net