Skip to main content
SpringerLink
Log in

Desynchronization of Pedal Motion: Crystallographic and Theoretical Study of (E)-4-[(4-ethylphenyl)diazenyl]-2-methylphenol

  • Original Paper
  • Published:
Journal of Chemical Crystallography Aims and scope Submit manuscript

Abstract

The single crystal X-ray diffraction analysis of the title compound, C15H16N2O, reveals that its molecules exhibit whole-molecule disorder at both crystal lattice sites due to pedal motion in solid state. The compound crystallizes in the monoclinic space group P 21/c with a = 20.5504(14) Å, b = 10.8887(5) Å, c = 12.0191(8) Å and β = 96.927(5)°. While major pedal conformers of the compound in solid state are stabilized by intermolecular O–H···N type hydrogen bonds leading to the formation of C(7) chains at Site 1 and C(8) chains at Site 2 along [0 1 0] axis, C–H···π type intermolecular interactions between major and minor conformers also serve to stabilize minor pedal conformers. An interesting feature about the crystal structure is that pedal conformers at Site 1 have two different occupancy factors arising from desynchronization of pedal motion along [2 1 0] direction in crystal phase. Quantum chemical calculations at the B3LYP/6-31++G** level suggest that the desynchronization of pedal motions make more unstable pedal conformers at Site 1 than those at Site 2.

Index Abstract

Molecular and crystal structure of (E)-4-[(4-ethylphenyl)diazenyl]-2-methylphenol, C16H18N2O, indicate desynchronization of pedal motion and the quantum chemical calculations at level of B3LYP/6-31++G** suggest that desynchronization of pedal motions make more unstable pedal conformers.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Scheme 1
Fig. 1
Fig. 2
Fig. 3
Fig. 4

Similar content being viewed by others

References

  1. Paul IC, Curtin DY (1973) Acc Chem Res 6:217–225

    Article  CAS  Google Scholar 

  2. Gavezzotti A, Simonetta M (1982) Chem Rev 82:1–13

    Article  CAS  Google Scholar 

  3. Harris KDM, Aliev AE (1995) Chem Br 31:132–136

    CAS  Google Scholar 

  4. Bürgi HB (2002) Faraday Discuss 122:41–63

    Article  Google Scholar 

  5. Finder CJ, Newton MG, Allinger NL (1974) Acta Cryst B30:411–415

    Google Scholar 

  6. Bernstein J (1975) Acta Cryst B31:1268–1271

    CAS  Google Scholar 

  7. Hoekstra A, Meertens P, Vos A (1975) Acta Cryst B31:2813–2817

    CAS  Google Scholar 

  8. Adams H, Allen RWK., Chin J, O’Sullivan B, Styring P, Sutton LR (2004) Acta Cryst E60:o289–o290

    CAS  Google Scholar 

  9. Bouwstra JA, Schouten A, Kroon J (1984) Acta Cryst C40:428–431

    CAS  Google Scholar 

  10. Brown CJ (1966) Acta Cryst 21:146–152

    Article  CAS  Google Scholar 

  11. Harada J, Ogawa K, Tomoda S (1997) Acta Cryst B53:662–672

    CAS  Google Scholar 

  12. Harada J, Uekusa H, Ohashi Y (1999) J Am Chem Soc 121:5809–5810

    Article  CAS  Google Scholar 

  13. Ito Y, Hosomi H, Ohba S (2000) Tetrahedron 56:6833–6844

    Article  CAS  Google Scholar 

  14. Ohba S, Hosomi H, Ito Y (2001) J Am Chem Soc 123:6349–6352

    Article  CAS  Google Scholar 

  15. Harada J, Ogawa K (2001) J Am Chem Soc 123:10884–10888

    Article  CAS  Google Scholar 

  16. Murugan NA, Yashonath S (2004) J Phy Chem B 108:17403

    Article  CAS  Google Scholar 

  17. Harada J, Ogawa K (2004) J Am Chem Soc 126:3539–3544

    Article  CAS  Google Scholar 

  18. Stoe & Cie, X-AREA (Version 1.18) and X-RED32 (Version 1.04), Darmstadt, Germany

  19. Sheldrick GM (2008) Acta Cryst A 64:112–122

    Article  Google Scholar 

  20. Stephens PJ, Devlin FJ, Chabalowski CF, Frisch MJ (1994) J Phys Chem 98:11623–11627

    Article  CAS  Google Scholar 

  21. Becke AD (1988) Phys Rev A 38:3098–3100

    Article  CAS  Google Scholar 

  22. Lee C, Yang W, Parr RG (1988) Phys Rev B 37:785–789

    Article  CAS  Google Scholar 

  23. Hariharan PC, Pople JA (1973) Theor Chim Acta 28:213–222

    Article  CAS  Google Scholar 

  24. Francl MM, Petro WJ, Hehre WJ, Binkley JS, Gordon MS, DeFrees DJ, Pople JA (1982) J Chem Phys 77:3654–3665

    Article  CAS  Google Scholar 

  25. Rassolov V, Pople JA, Ratner M, Windus TL (1998) J Chem Phys 109:1223–1229

    Article  CAS  Google Scholar 

  26. Hypercube (2003). HyperChem, Version 7.52. Hypercube Inc., 1115 NW 4th Street, Gainsville, FL 32601-4256, USA

  27. Fletcher P (1990) Practical methods of optimization. Wiley, New York. pp 84–86

    Google Scholar 

  28. Spek AL (2003) J Appl Cryst 36:7–13

    Article  CAS  Google Scholar 

  29. Albayrak Ç, Odabaşoğlu M, Büyükgüngör O, Lönnecke P (2004) Acta Cryst C60:o318–o320

    CAS  Google Scholar 

  30. Ocak-İskeleli N, Karabıyık H, Albayrak Ç, Petek H, Ağar E (2006) J Chem Cryst 36:709–714

    Article  Google Scholar 

  31. Ocak-İskeleli N, Karabıyık H, Albayrak Ç, Petek H, Ağar E (2006) Struct Chem 17:393–399

    Article  Google Scholar 

  32. Karabıyık H., Ocak-İskeleli N., Albayrak Ç, Ağar E (2007) Struct Chem 18:87–93

    Article  Google Scholar 

  33. Ocak-İskeleli N, Karabıyık H, Albayrak Ç, Ağar E, Gümrükçüoğlu İE (2008) Struct Chem (in press)

  34. Jiménez-Cruz F, Pérez-Caballero G, Hernández-Ortega S, Rubio-Arroyo M (2000) Acta Cryst C 56:1028–1029

    Article  Google Scholar 

  35. Bernstein J, Davis RE, Shimoni L, Chang N-L (1995) Angew Chem Int Ed Engl 34:1555–1573

    Article  CAS  Google Scholar 

Download references

Acknowledgment

Hasan Karabıyık would like to thank TÜBİTAK (The Scientific and Technical Research Council of Turkey) for partial financial support.

Author information

Authors and Affiliations

  1. Department of Science Education, Ondokuz Mayıs University, 55200, Samsun, Turkey

    Nazan Ocak-İskeleli

  2. Department of Physics, Dokuz Eylül University, Fen Edebiyat Fakültesi, Fizik Bölümü, Tinaztepe Kampusu, 35160, Izmir, Turkey

    Hasan Karabıyık

  3. Department of Chemistry, Ondokuz Mayıs University, 55139, Samsun, Turkey

    Çiğdem Albayrak & Erbil Ağar

Authors
  1. Nazan Ocak-İskeleli
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Hasan Karabıyık
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Çiğdem Albayrak
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Erbil Ağar
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Hasan Karabıyık.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Ocak-İskeleli, N., Karabıyık, H., Albayrak, Ç. et al. Desynchronization of Pedal Motion: Crystallographic and Theoretical Study of (E)-4-[(4-ethylphenyl)diazenyl]-2-methylphenol. J Chem Crystallogr 38, 671–677 (2008). https://doi.org/10.1007/s10870-008-9371-5

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10870-008-9371-5

Keywords

Search

Navigation