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Synthesis and Crystal Structure of 5-[2-(6-bromonaphthalenyloxymethyl)]-3-(4-morpholinomethyl)-1,3,4-oxadiazole-2(3H)-thione

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Abstract

The title compound, C18H18BrN3O3S, a derivative of 1,3,4-oxadiazole, crystallizes in the triclinic space group P-1 with unit cell parameters a = 6.8731(3), b = 8.9994(4), c = 15.7099(6) Å, α = 92.779(3)°, β = 130.575(3)°, γ = 107.868(4)°, Z = 2. The dihedral angle between the mean planes of the planar naphthyl and morpholine (chair) rings with the planar oxadiazol ring is 50.1(8) and 76.8(6)°, respectively. The planar naphthyl ring is twisted 52.2(5)° with the mean plane of the morpholine ring. A group of four intermolecular close contacts are observed between a bromine atom and hydrogen atoms from the closely packed naphthyl, morpholine and oxy–methyl groups in the unit cell. These molecular interactions in concert with an additional series of π–π stacking interactions that occur between the center of gravity of the two 6-membered rings of the naphthalene group influence the twist angles of each of these three groups. A MOPAC AM1 calculation of the conformation energy of the crystal structure [226.0128(9) kcal] compared to that of the minimum energy structure after geometry optimization [29.9744(1) kcal] reveals a significantly reduced value. The twist angles of the three groups above also change after the AM1 calculation giving support to the influence of both intermolecular C–H···Br short-range interactions and Cg π–π stacking interactions on these angles which therefore play a role in stabilizing crystal packing.

Graphical Abstract

Crystal structure of 5-{[(6-bromonaphthalen-2-yl)oxy]methyl}-3-(morpholin-4-ylmethyl)-1,3,4-oxadiazole-2(3H)-thione, C18H18BrN3O3S, is reported and its geometric and packing parameters described and compared to a MOPAC computational calculation.

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References

  1. Ainsworth C (1965) J Am Chem Soc 87:5800–5803. doi:10.1021/ja00952a056

    Article  CAS  Google Scholar 

  2. Kulkarni AP, Tonzola CJ, Babel A, Jenekhe SA (2004) Chem Mater 16:4556–4573. doi:10.1021/cm049473l

    Article  CAS  Google Scholar 

  3. Paik K, Baek NS, Kim HK, Lee J, Lee Y (2002) Macromol 35:6782–6791. doi:10.1021/ma020406r

    Article  CAS  Google Scholar 

  4. Amir M, Kumar S (2007) Acta Pharm 57:31–45. doi:10.2478/v10007-007-0003-y

    Article  CAS  Google Scholar 

  5. Rajak H, Kharya M, Mishra P (2007) Pharm Soc Jpn 127:1757–1764

    CAS  Google Scholar 

  6. Cai X, Grewal G, Mark LG, Anna TP (2003) USPat No.6555550

  7. Verhyde B, Dehaen W (2001) J Org Chem 66:4062–4064. doi:10.1021/jo005772s

    Article  Google Scholar 

  8. Wang Y, Sauer DR, Djurie SW (2006) Tetrahedron Lett 47:105–108. doi:10.1016/j.tetlet.2005.10.131

    Article  CAS  Google Scholar 

  9. Ramalingam T, Deshmukh AA, Sattur PB, Sheth UK, Naik SR (1981) J Indian Chem Soc 58:269–271

    CAS  Google Scholar 

  10. Kagthara PR, Shah NS, Doshi RK, Parekh HH (1999) Indian J Chem 38B:572–576

    CAS  Google Scholar 

  11. Nagalakshmi G (2008) Indian J Pharm Sci 70:49–55

    Article  Google Scholar 

  12. El-Emam AA, Al-Deeb OA, Al-Omar M (2004) Bioorg Med Chem 12:5107–5113. doi:10.1016/j.bmc.2004.07.033

    Article  CAS  Google Scholar 

  13. Kucukguzel SG, Oruc EE, Rollas S, Sahin F, Ozbek A (2002) Eur J Med Chem 37:197–206. doi:10.1016/S0223-5234(01)01326-5

    Article  CAS  Google Scholar 

  14. Honnalli SS, Ronald PM, Vijaybhasker K, Hukkeri VI, Kumar R (2005) Communio 11:505–508

    CAS  Google Scholar 

  15. Mullican MD, Wilson MW, Connor DT, Kostlan CR, Schrier DJ, Dyer RD (1993) J Med Chem 36:1090–1099. doi:10.1021/jm00060a017

    Article  CAS  Google Scholar 

  16. Amir M, Kumar S (2004) Eur J Med Chem 39:535–545. doi:10.1016/j.ejmech.2004.02.008

    Article  CAS  Google Scholar 

  17. Andreani A, Rambaldi M, Locatelli A, Pifferi G (1994) Eur J Med Chem 29:903–906. doi:10.1016/0223-5234(94)90115-5

    Article  CAS  Google Scholar 

  18. Misra U, Hitkari K, Saxena AK, Gurtu S, Shankar K (1996) Eur J Med Chem 31:629–634. doi:10.1016/0223-5234(96)89559-6

    Article  CAS  Google Scholar 

  19. Narayana B, Ashalatha BV, Vijaya Raj KK, Fernandes J, Sarojini BK (2005) Bioorg Med Chem 13:4638–4644. doi:10.1016/j.bmc.2005.04.068

    Article  CAS  Google Scholar 

  20. Narayana B, Vijaya Raj KK, Ashalatha BV, Suchetha Kumari N (2005) Arch Pharm 338:373–377. doi:10.1002/ardp.200500974

    Article  CAS  Google Scholar 

  21. Yathirajan HS, Bindya S, Ashalatha BV, Narayana B, Bolte M (2006) Acta Crystallogr E62:o4442–o4443

    CAS  Google Scholar 

  22. Sheldrick GM (1997) SHELXS97, SHELXL97. University of Gőttingen, Germany

  23. Bruker (2006) SHELXTL, Bruker A XS Inc., Madison, Wisconsin, USA

  24. Allen FH, Kennard O, Watson DG, Brammer L, Orpen AG, Taylor RJ (1987) Chem Soc Perkin Trans 2:S1–S19. doi:10.1039/p298700000s1

    Article  Google Scholar 

  25. Cremer D, Pople JA (1975) J Am Chem Soc 97:1354–1358. doi:10.1021/ja00839a011

    Article  CAS  Google Scholar 

  26. Cambridge Structural Database (2003–2007) Cambridge Crystallographic Centre, MOGUL.1.1.2

  27. AM1 (Austin Model 1) (2007) Approximation together with the Hartree-Fock closed-shell (restricted) wavefunction was used and minimizations were teminnated at an r.m.s. gradient of less than 0.01 kJ mol−1 Å−1. Schmidt, J.R.; Polik, W.F. WebMO Pro, version 8.0.010e; WebMO, LLC: Holland, MI, USA. available from http://www.webmo.net

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Acknowledgments

ANM thanks the University of Mysore for use of their research facilities. RJB acknowledges the NSF MRI program (grant No. CHE-0619278) for funds to purchase an 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, Mangalagangotri, 574 199, India

    B. Narayana

  5. Department of Chemistry, P.A. College of Engineering, Mangalore, 574 153, India

    B. K. Sarojini

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  1. Jerry P. Jasinski
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  2. Ray J. Butcher
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  4. H. S. Yathirajan
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Correspondence to Jerry P. Jasinski.

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Jasinski, J.P., Butcher, R.J., Mayekar, A.N. et al. Synthesis and Crystal Structure of 5-[2-(6-bromonaphthalenyloxymethyl)]-3-(4-morpholinomethyl)-1,3,4-oxadiazole-2(3H)-thione. J Chem Crystallogr 39, 761–765 (2009). https://doi.org/10.1007/s10870-009-9570-8

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