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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

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 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

Keywords

Chalcones Crystal structure Hydrogen bonds Naphthyl Pyridyl Phenyl Syn Trans 

Notes

Acknowledgements

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.

References

  1. 1.
    Dimmock JR, Elias DW, Beazely MA, Kandepu NM (1999) Curr Med Chem 6:1125–1149Google Scholar
  2. 2.
    Nowakowska Z, Wyrzykiewicz E, Kedzia B (2001) Il Farmaco 56:325–329CrossRefGoogle Scholar
  3. 3.
    Nowakowska Z (2007) Eur J Med Chem 42:125–137CrossRefGoogle Scholar
  4. 4.
    Edwards ML, Stemarick DM, Sabol JS, Diekema KA, Dinerstein RJ (1994) J Med Chem 37:4357–4362CrossRefGoogle Scholar
  5. 5.
    Go ML, Wu X, Liu XL (2005) Curr Med Chem 12:483–499Google Scholar
  6. 6.
    Oxford Diffraction, CrysAlisPro (Version 171.31.8) and CrysAlis RED (Version 1.171.31.8). Oxford Diffraction Ltd., Abingdon, Oxfordshire, England, 2007Google Scholar
  7. 7.
    Sheldrick GM (1997) SHELXS97 and SHELXL97. University of Göttingen, GermanyGoogle Scholar
  8. 8.
    Bruker SHELXTL. Version 6.10 (2000) Bruker AXS Inc., Madison, Wisconsin, USAGoogle Scholar
  9. 9.
    Allen FH, Kennard O, Watson DG, Brammer L, Orpen AG, Taylor RJ (1987) Chem Soc Perkin Trans 2:S1–19CrossRefGoogle Scholar
  10. 10.
    Cremer D, Pople JA (1975) J Am Chem Soc 97:1354–1358CrossRefGoogle Scholar
  11. 11.
    Yathirajan HS, Narayana B, Ashalatha BV, Sarojini BK, Bolte M (2006) Acta Cryst E62:o4440–o4441Google Scholar
  12. 12.
    Yathirajan HS, Mayekar AN, Sarojini BK, Narayana B, Bolte M (2007) Acta Cryst E63:o1012–o1013Google Scholar
  13. 13.
    Yathirajan HS, Mayekar AN, Sarojini BK, Narayana B, Bolte M (2007a) Acta Cryst E63:o1140–o1141Google Scholar
  14. 14.
    Butcher RJ, Yathirajan HS, Ashalatha BV, Narayana B, Sarojini BK (2007) Acta Cryst E63:o1430–o1431Google Scholar
  15. 15.
    Stewart JJ (1990) MOPAC, A General Molecular Orbital Package, Frank J. Seiler Research Lab, United States Air Force Academy, No. ADA233489Google Scholar
  16. 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
  17. 17.
    Bondi AJ (1964) Phys Chem 65:441–451CrossRefGoogle Scholar

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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