Skip to main content
SpringerLink
Log in

Different Hydrogen-Bonded Interactions in the Cocrystals of Nicotinamide with Two Aromatic Acids

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

Abstract

Nicotinamide crystallizes with 3-hydroxy-2-naphthoic acid and 4-aminobenzoic acid to give rise to cocrystal 1 and 2, respectively. Cocrystal 1, [C11H8O3][C6H6N2O], crystallizes in the monoclinic space group C2/c with a = 25.810(4), b = 4.8932(5), c = 23.869(4) Å, β = 107.078(8)º, V = 2881.6(7) Å3, Z = 8, C17H14N2O4, M r  = 310.30, D c  = 1.431 g/cm3. Cocrystal 2, [C7H7NO2][C6H6N2O]·H2O, crystallizes in the triclinic space group P-1 with a = 7.214(5), b = 7.326(5), c = 13.484(11) Å, α = 83.23(2), β = 77.189(18), γ = 80.35(2)º, V = 682.7(9) Å3, Z = 2, C13H15N3O4, M r  = 277.28, D c  = 1.349 g/cm3. Similar carboxylic acid···pyridine synthon R 22 (7) can be observed in the two cocrystals. In 1, amide of nicotinamide forms a C(4) chain from the anti H to its carbonyl oxygen. In 2, the amide forms a R 22 (8) homodimer which is linked into 2D layer by water molecule through different hydrogen-bonding interactions. The 3D hydrogen-bonded structure results from a synthon R 24 (8) from amide, water and amino group of 4-aminobenzoic acid.

Graphical Abstract

Nicotinamide crystallizes with 3-hydroxy-2-naphthoic acid and 4-aminobenzoic acid to give rise to cocrystal 1 and 2, respectively. Similar carboxylic acid···pyridine synthon R 22 (7) can be observed in the two cocrystals. In 1, amide of nicotinamide forms a C(4) chain from the anti H to its carbonyl oxygen. The syn H is accepted by hydroxyl oxygen of 3-hydroxy-2-naphthoic acid to form an infinite C 22 (12) chain. In 2, the amide forms a R 22 (8) homodimer which is linked into 2D layer by water molecule through different hydrogen-bonding interactions. The 3D hydrogen-bonded structure results from a synthon R 24 (8) from amide, water and amino group of 4-aminobenzoic acid.

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

Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5

Similar content being viewed by others

References

  1. Desiraju GR (1997) Chem Commun 16:1475–1482

    Article  Google Scholar 

  2. Almarsson Ö, Zaworotko MJ (2004) Chem Commun 17:1889–1896

    Article  Google Scholar 

  3. Basavoju S, Boström D, Velaga SP (2008) Pharma Res 25:53–541

    Article  Google Scholar 

  4. Childs SL, Chyall LJ, Dunlap JT, Smolenskaya VN, Stahly BC, Stahly GP (2004) J Am Chem Soc 126:13335–13342

    Article  CAS  Google Scholar 

  5. Trask AV (2007) Mol Pharma 4:301–309

    Article  CAS  Google Scholar 

  6. Fleischman SG, Kuduva SS, McMahon JA, Moulton B, Bailey Walsh RD, Rodríguez-Hornedo N, Zaworotko MJ (2003) Cryst Growth Des 3:909–919

    Article  CAS  Google Scholar 

  7. Báthori NB, Lemmerer A, Venter GA, Bourne SA, Caira MR (2011) Cryst Growth Des 11:75–87

    Article  Google Scholar 

  8. Nicoli S, Bilzi S, Santi P, Caira MR, Li J, Bettini R (2008) J Pharma Sci 97:4830–4839

    Article  CAS  Google Scholar 

  9. Cheney ML, Shan N, Healey ER, Hanna M, Wojtas L, Zaworotko MJ, Sava V, Song S, Sanchez-Ramos JR (2010) Cryst Growth Des 10:394–405

    Article  CAS  Google Scholar 

  10. Arenas-García JI, Herrera-Ruiz D, Mondragón-Vásquez K, Morales-Rojas H, Höpfl H (2010) Cryst Growth Des 10:3732–3742

    Article  Google Scholar 

  11. Berry DJ, Seaton CC, Clegg W, Harrington RW, Coles SJ, Horton PN, Hursthouse MB, Storey R, Jones W, Friščić T, Blagden N (2008) Cryst Growth Des 8:1697–1712

    Article  CAS  Google Scholar 

  12. Lemmerer A, Esterhuysen C, Bernstein J (2010) J Pharma Sci 99:4054–4071

    CAS  Google Scholar 

  13. Rigaku (2000) CrystalClear Programs for data collection, cell refinement and structure solution. Rigaku Corp, Japan

  14. Sheldrick GM (2008) Acta Crystallogr Sect A 64:112–122

    Article  Google Scholar 

  15. Centore R, Carella A, Tuzi A, Capobianco A, Pelusob A (2010) CrystEngComm 12:1186–1193

    Article  CAS  Google Scholar 

Download references

Acknowledgments

The work was supported by the Program for New Century Excellent Talents in Fujian Province University (JK2010043). S. Hu appreciates the grant from Undergraduate Innovative Research Program of Minjiang University (mjcxx1008).

Author information

Authors and Affiliations

  1. Department of Chemistry and Chemical Engineering, Minjiang University, Fuzhou, 350108, China

    Benyong Lou & Shuling Hu

Authors
  1. Benyong Lou
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Shuling Hu
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Benyong Lou.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Lou, B., Hu, S. Different Hydrogen-Bonded Interactions in the Cocrystals of Nicotinamide with Two Aromatic Acids. J Chem Crystallogr 41, 1663–1668 (2011). https://doi.org/10.1007/s10870-011-0154-z

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10870-011-0154-z

Keywords

Search

Navigation