Journal of Chemical Crystallography

, Volume 39, Issue 8, pp 603–606 | Cite as

Crystal and Molecular Structure of the 1:2 Salt Formed Between 1,2-(4-Pyridyl)Ethane and 2-(4-Hydroxyphenylazo)Benzoic Acid

  • Ellen M. Corlette
  • Edward R. T. Tiekink
Original Paper


Proton transfer occurred during co-crystallization of 1,2-(4-pyridyl)ethane with 2-(4-hydroxyphenylazo)benzoic acid to yield a salt comprising a 1:2 ratio of 1,2-bis(4-pyridinium)ethane dications and 2-(4-hydroxyphenylazo)benzoate anions. Centrosymmetrically related anions associate by charge-assisted O–H···O hydrogen bonds to form 24-membered {···OC3N2C4OH}2 synthons. These are connected into a supramolecular polymer via charge-assisted N–H···O hydrogen bonds involving the 1,2-bis(4-pyridinium)ethane dications. The compound crystallizes in the triclinic space group P−1 with a = 8.517(4) Å, b = 9.110(5) Å, c = 10.477(5) Å, α = 96.850(13)°, β = 94.446(12)°, γ = 104.946(10)° and Z = 1 {two anions and a dication}.

Index Abstract

Supramolecular chains mediated by charge-assisted O–H···O and N–H···O hydrogen bonding are found in the salt containing a 1:2 ratio of 1,2-bis(4-pyridinium)ethane dications and 2-(4-hydroxyphenylazo)benzoate anions.


Organic salt Hydrogen bonding Charge-assisted hydrogen bonding 


  1. 1.
    Vishweshwar P, McMahon JA, Zaworotko MJ (2006) In: Tiekink ERT, Vittal JJ (eds) Frontiers in Crystal Engineering. Wiley, Chichester Chapter 2Google Scholar
  2. 2.
    Hickey MB, Peterson ML, Scoppettuolo LA, Morrisette SL, Vetter A, Guzmán H, Remenar JF, Zang Z, Tawa MD, Haley S, Zaworotko MJ, Almarsson Ö (2007) Eur J Pharm Biopharm 67:112. doi: 10.1016/j.ejpb.2006.12.016 CrossRefGoogle Scholar
  3. 3.
    Zukerman-Schpector J, Tiekink ERT (2008) Z Kristallogr 223:233. doi: 10.1524/zkri.2008.0021 CrossRefGoogle Scholar
  4. 4.
    Weyna DR, Shattock T, Reddy V, Zaworotko MJ (2008) Cryst Growth Des 8:4533. doi: 10.1021/cg800565a CrossRefGoogle Scholar
  5. 5.
    Portalone G, Colapietro MJ (2004) J Chem Crystallogr 34:609. doi: 10.1023/B:JOCC.0000044088.22773.fa CrossRefGoogle Scholar
  6. 6.
    Trask AV, Motherwell SWD, Jones W (2005) Cryst Growth Des 5:1013. doi: 10.1021/cg0496540 CrossRefGoogle Scholar
  7. 7.
    Cheney ML, McManus JG, Perman JA, Wang Z, Zaworotko MJ (2007) Cryst Growth Des 7:616. doi: 10.1021/cg0701729 CrossRefGoogle Scholar
  8. 8.
    Chiarella AR, Davey JR, Peterson LM (2007) Cryst Growth Des 7:1223. doi: 10.1021/cg070218y CrossRefGoogle Scholar
  9. 9.
    Zaworotko MJ, Cheney ML (2008) Materials and methods for co-crystal controlled solid-state synthesis of imides and imines. PCT Int. Appl. WO 2008073613, 134ppGoogle Scholar
  10. 10.
    Trask AV (2007) Mol Pharmacol 4:301. doi: 10.1021/mp070001z CrossRefGoogle Scholar
  11. 11.
    Desiraju GR (2003) J Ind Chem Soc 80:151Google Scholar
  12. 12.
    Bernstein J (2006) Polymorphism 365Google Scholar
  13. 13.
    Remenar JF, Morissette SL, Peterson ML, Moulton B, MacPhee JM, Guzmán HR, Almarsson Ö (2003) J Am Chem Soc 25:8456. doi: 10.1021/ja035776p CrossRefGoogle Scholar
  14. 14.
    Childs SL, Chyall LJ, Dunlap JT, Smolenskaya VN, Stahly BC, Stahly GP (2004) J Am Chem Soc 126:13335. doi: 10.1021/ja048114o CrossRefGoogle Scholar
  15. 15.
    Blagden N, de Matas M, Gavan PT, York P (2007) Adv Drug Deliv Rev 59:617. doi: 10.1016/j.addr.2007.05.011 CrossRefGoogle Scholar
  16. 16.
    Shan N, Zaworotko MJ (2008) Drug Discov Today 13:440. doi: 10.1016/j.drudis.2008.03.004 CrossRefGoogle Scholar
  17. 17.
    Bis J, Vishweshwar P, Weyna D, Zaworotko MJ (2007) Mol Pharm 4:401. doi: 10.1021/mp070012s CrossRefGoogle Scholar
  18. 18.
    Aakeröy CB, Desper J, Fasulo M, Hussain I, Levin B, Schultheiss N (2008) CrystEngComm 10:1816. doi: 10.1039/b811809d CrossRefGoogle Scholar
  19. 19.
    Shattock TR, Arora KK, Vishweshwar P, Zaworotko MJ (2008) Cryst Growth Des 8:4533. doi: 10.1021/cg800565a CrossRefGoogle Scholar
  20. 20.
    Broker GA, Tiekink ERT (2007) CrystEngComm 9:1096. doi: 10.1039/b707690h CrossRefGoogle Scholar
  21. 21.
    Ellis CA, Tiekink ERT, Zukerman-Schpector J (2008) J Chem Crystallogr 38:513. doi: 10.1007/s10870-008-9331-010.1007/s10870-008-9331-0 CrossRefGoogle Scholar
  22. 22.
    Broker GA, Bettens RPA, Tiekink ERT (2008) CrystEngComm 10:879. doi: 10.1039/b800797g CrossRefGoogle Scholar
  23. 23.
    Ellis CA, Miller MA, Spencer J, Zukerman-Schpector J, Tiekink ERT (2009) CrystEngComm (in press).
  24. 24.
    Higashi T (1995) ABSCOR. Rigaku Corporation, TokyoGoogle Scholar
  25. 25.
    CrystalClear (2005) User manual. Rigaku/MSC Inc. Rigaku Corporation, The WoodlandsGoogle Scholar
  26. 26.
    Sheldrick GM (2008) Acta Crystallogr A 64:211CrossRefGoogle Scholar
  27. 27.
    Johnson CK (1976) ORTEP II, Report ORNL-5136. Oak Ridge National Laboratory, Oak RidgeGoogle Scholar
  28. 28.
    Crystal Impact (2006) DIAMOND. Version 3.1c. Crystal Impact GbR. Postfach 1251:D-53002. Bonn, GermanyGoogle Scholar
  29. 29.
    teXsan (1992) Structure analysis package. Molecular Structure Corporation, HoustonGoogle Scholar
  30. 30.
    Spek AL (2003) J Appl Cryst 36:7. doi: 10.1107/S0021889802022112 CrossRefGoogle Scholar
  31. 31.
    Ide S, Karacan N, Tufan Y (1995) Acta Crystallogr C 51:2304. doi: 10.1107/S0108270195005221 CrossRefGoogle Scholar
  32. 32.
    Qian H, Huang W (2005) J Mol Struct 743:191. doi: 10.1016/j.molstruc.2005.03.001 CrossRefGoogle Scholar
  33. 33.
    Etter MC, MacDonald JC, Bernstein J (1990) Acta Crystallogr B 46:246. doi: 10.1107/S0108768189012929 CrossRefGoogle Scholar
  34. 34.
    Allen FH (2002) Acta Crystallogr B 58:380. doi: 10.1107/S0108768102003890 CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media, LLC 2009

Authors and Affiliations

  1. 1.Department of ChemistryThe University of Texas at San AntonioSan AntonioUSA

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