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

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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) 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.

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References

  1. Dimmock JR, Elias DW, Beazely MA, Kandepu NM (1999) Curr Med Chem 6:1125–1149

    CAS  Google Scholar 

  2. Nowakowska Z, Wyrzykiewicz E, Kedzia B (2001) Il Farmaco 56:325–329

    Article  CAS  Google Scholar 

  3. Nowakowska Z (2007) Eur J Med Chem 42:125–137

    Article  CAS  Google Scholar 

  4. Edwards ML, Stemarick DM, Sabol JS, Diekema KA, Dinerstein RJ (1994) J Med Chem 37:4357–4362

    Article  CAS  Google Scholar 

  5. Go ML, Wu X, Liu XL (2005) Curr Med Chem 12:483–499

    CAS  Google Scholar 

  6. Oxford Diffraction, CrysAlisPro (Version 171.31.8) and CrysAlis RED (Version 1.171.31.8). Oxford Diffraction Ltd., Abingdon, Oxfordshire, England, 2007

  7. Sheldrick GM (1997) SHELXS97 and SHELXL97. University of Göttingen, Germany

    Google Scholar 

  8. Bruker SHELXTL. Version 6.10 (2000) Bruker AXS Inc., Madison, Wisconsin, USA

  9. Allen FH, Kennard O, Watson DG, Brammer L, Orpen AG, Taylor RJ (1987) Chem Soc Perkin Trans 2:S1–19

    Article  Google Scholar 

  10. Cremer D, Pople JA (1975) J Am Chem Soc 97:1354–1358

    Article  CAS  Google Scholar 

  11. Yathirajan HS, Narayana B, Ashalatha BV, Sarojini BK, Bolte M (2006) Acta Cryst E62:o4440–o4441

    CAS  Google Scholar 

  12. Yathirajan HS, Mayekar AN, Sarojini BK, Narayana B, Bolte M (2007) Acta Cryst E63:o1012–o1013

    CAS  Google Scholar 

  13. Yathirajan HS, Mayekar AN, Sarojini BK, Narayana B, Bolte M (2007a) Acta Cryst E63:o1140–o1141

    CAS  Google Scholar 

  14. Butcher RJ, Yathirajan HS, Ashalatha BV, Narayana B, Sarojini BK (2007) Acta Cryst E63:o1430–o1431

    CAS  Google Scholar 

  15. Stewart JJ (1990) MOPAC, A General Molecular Orbital Package, Frank J. Seiler Research Lab, United States Air Force Academy, No. ADA233489

  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. Bondi AJ (1964) Phys Chem 65:441–451

    Article  Google Scholar 

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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.

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Authors and Affiliations

  1. Department of Chemistry, Keene State College, 229 Main Street, Keene, NH, 03435-2001, USA

    Jerry P. Jasinski

  2. Department of Chemistry, Howard University, 525 College Street NW, Washington, DC, 20059, USA

    Ray J. Butcher

  3. Department of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore, 570 006, India

    Anil N. Mayekar & H. S. Yathirajan

  4. Department of Studies in Chemistry, Mangalore University, Mangalagngotri, Mangalore, 574 199, India

    B. Narayana

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  1. Jerry P. Jasinski
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  2. Ray J. Butcher
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Correspondence to Jerry P. Jasinski.

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Jasinski, J.P., Butcher, R.J., Mayekar, A.N. et al. Structures of Three Chalcones Derived from 6-Methoxy-2-naphthaldehyde. J Chem Crystallogr 39, 157–162 (2009). https://doi.org/10.1007/s10870-008-9446-3

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