Journal of Chemical Crystallography

, Volume 39, Issue 3, pp 157–162 | Cite as

Structures of Three Chalcones Derived from 6-Methoxy-2-naphthaldehyde

  • Jerry P. Jasinski
  • Ray J. Butcher
  • Anil N. Mayekar
  • H. S. Yathirajan
  • B. Narayana
Original Paper


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 IIII 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].

Index Abstract

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


Chalcones 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.


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Copyright information

© Springer Science+Business Media, LLC 2008

Authors and Affiliations

  • Jerry P. Jasinski
    • 1
  • Ray J. Butcher
    • 2
  • Anil N. Mayekar
    • 3
  • H. S. Yathirajan
    • 3
  • B. Narayana
    • 4
  1. 1.Department of ChemistryKeene State CollegeKeeneUSA
  2. 2.Department of ChemistryHoward UniversityWashingtonUSA
  3. 3.Department of Studies in ChemistryUniversity of MysoreMysoreIndia
  4. 4.Department of Studies in ChemistryMangalore UniversityMangaloreIndia

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