Three New Compounds Derived from Nitrofurantoin: X-Ray Structures and Hirshfeld Surface Analyses


The polymorphism of nitrofurantoin (NF), 1), the cocrystals of NF:2,2’-bipyridyl = 2:1, 2) and NF: 1,10-phenanthroline = 1:1, 3) have been prepared and characterized. The crystal structure analyses show that there are various weak forces among the molecules, such as C/N-H···O, N-H···N hydrogen bond interactions and π···π/lone pair stacking interactions, which play a key role in the assembly of supramolecular networks. A thorough analysis of Hirshfeld surfaces and fingerprint plots facilitates a comparison of intermolecular interactions in 1 - 3, which are crucial in building supramolecular architectures.

Share and Cite:

Wang, H. , Xiao, H. , Liu, N. , Zhang, B. and Shi, Q. (2015) Three New Compounds Derived from Nitrofurantoin: X-Ray Structures and Hirshfeld Surface Analyses. Open Journal of Inorganic Chemistry, 5, 63-73. doi: 10.4236/ojic.2015.53008.

Conflicts of Interest

The authors declare no conflicts of interest.


[1] Seth, S.K., Manna, P., Singh, N.J., Mitra, M., Jana, A.D., Das, A., Choudhury, S.R., Kar, T., Mukhopadhyay, S. and Kim, K.S. (2013) Molecular Architecture Using Novel Types of Non-Covalent π-Interactions Involving Aromatic Neutrals, Aromatic Cations and π-Anions. CrystEngComm, 15, 1285-1288.
[2] Boer, S.A., Hawes, C.S. and Turner, D.R. (2014) Engineering Entanglement: Controlling the Formation of Polycatenanes and Polyrotaxanes Using π-Interactions. Chemical Communications, 50, 1125-1127.
[3] Brancatelli, G., Pappalardo, S., Gattuso, G., Notti, A., Pisagatti, I., Parisi, M.F. and Geremia, S. (2014) Hydrogen Bond-Assisted Solid-State Formation of a Salt-Bridged Calix[5] Arene Pseudo-Dimer. CrystEngComm, 16, 89-93.
[4] Nishio, M., Umezawa, Y., Fantini, J., Weiss, M.S. and Chakrabarti, P. (2014) CH-π Hydrogen Bonds in Biological Macromolecules. Physical Chemistry Chemical Physics, 16, 12648-12683.
[5] Black, H.T. and Perepichka, D.F. (2014) Crystal Engineering of Dual Channel p/n OrganicSemiconductors by Complementary Hydrogen Bonding. Angewandte Chemie, 126, 2170-2174.
[6] Kadam, R.U., Garg, D., Schwartz, J., Visini, R., Sattler, M., Stocker, A., Darbre, T. and Reymond, J.L. (2013) CH-π “T-Shape” Interaction with Histidine Explains Binding of Aromatic Galactosides to Pseudomonas aeruginosa Lectin LecA. ACS Chemical Biology, 8, 1925-1930.
[7] Takahashi, O., Kohno, Y. and Nishio, M. (2010) Relevance of Weak Hydrogen Bonds in the Conformation of Organic Compounds and Bioconjugates: Evidence from Recent Experimental Data and High-Level ab Initio MO Calculations. Chemical Reviews, 110, 6049-6076.
[8] Pienaar, E.W., Caira, M.R. and Lötter, A.P. (1993) Polymorphs of Nitrofurantoin. I. Preparation and X-Raycrystal Structures of Two Monohydrated Forms of Nitrofurantoin. Journal of Crystallographic and Spectroscopic Research, 23, 739-744.
[9] Ertan, G., Karasulu, Y. and Güneri, T. (1993) Degradation and Gastrointestinal Stability of Nitrofurantoin in Acidic and Alkaline Media. International Journal of Pharmaceutics, 96, 243-248.
[10] Cherukuvada, S., Babu, N.J. and Nangia, A. (2011) Nitrofurantoin–p-Aminobenzoic Acid Cocrystal: Hydration Stability and Dissolution Rate Studies. Journal of Pharmaceutical Sciences, 100, 3233-3244.
[11] Tutughamiarso, M., Bolte, M., Wagner, G. and Egert, E. (2011) Five Pseudopolymorphs and a Cocrystal of Nitrofurantoin. Acta Crystallographica Section C, 67, o18-o25.
[12] Vangala, V.R., Chow, P.S. and Tan, R.B.H. (2012) Co-Crystals and Co-Crystal Hydrates of the Antibiotic Nitrofurantoin: Structural Studies and Physicochemical Properties. Crystal Growth & Design, 12, 5925-5938.
[13] Vangala, V.R., Chow, P.S. and Tan, R.B.H. (2013) The Solvates and Salt of Antibiotic Agent, Nitrofurantoin: Structural, Thermochemical and Desolvation Studies. CrystEngComm, 15, 878-889.
[14] Babu, N.J., Cherukuvada, S., Thakuria, R. and Nangia,A. (2010) Conformational and Synthon Polymorphism in Furosemide (Lasix). Crystal Growth & Design, 10, 1979-1989.
[15] McKinnon, J.J., Spackman, M.A. and Mitchell, A.S. (2004) Novel Tools for Visualizing and Exploring Intermolecular Interactions in Molecular Crystals. Acta Crystallographica Section B, 60, 627-668.
[16] Spackman, M.A. and Jayatilaka, D. (2009) Hirshfeld Surface Analysis. CrystEngComm, 11, 19-32.
[17] McKinnon, J.J., Jayatilaka, D. and Spackman, M.A. (2007) Towards Quantitative Analysis of Intermolecular Interactions with Hirshfeld Surfaces. Chemical Communications, No. 37, 3814-3816.
[18] Manna, P., Seth, S.K., Das, A., Hemming, J., Prendergast, R., Helliwell, M., Choudhury, S.R., Frontera, A. and Mukhopadhyay, S. (2012) Anion Induced Formation of Supramolecular Associations Involving Lone Pair-π and Anion-π Interactions in Co(II) Malonate Complexes: Experimental Observations, Hirshfeld Surface Analyses and DFT Studies. Inorganic Chemistry, 51, 3557-3571.
[19] Luo, Y.H., Wu, D.E., Song, W.T., Ge, S.W. and Sun, B.W. (2014) Positions of Amino Groups on Ammonium Salts Tunes the Conformations of Crown Ethers: Crystal Structures, Hirshfeld Surfaces and Spectroscopic Studies. CrystEngComm, 16, 5319-5330.
[20] Sheldrick, G.M. (2004) APEX-II, SAINT-Plus and TWINABS. Bruker-Nonius AXS Inc., Madison.
[21] Sheldrick, G.M. (2002) SAINT (Version 6.02), SADABS (Version 2.03). Bruker AXS Inc., Madison.
[22] Sheldrick, G.M. (2002) SHELXTL (Version 6.10). Bruker AXS Inc., Madison.
[23] Sheldrick, G.M. (1997) SHELXL-97, Program for X-ray Crystal Structure Solution and Refinement. University of Göttingen, Göttingen.
[24] Wolff, S.K., Grimwood, D.J., McKinnon, J.J., Turner, M.J., Jayatilaka, D. and Spackman, M.A. (2012) Crystal Explorer 3.0. University of Western Australia, Perth.
[25] Allen, F.H., Kennard, O., Watson, D.G., Brammer, L., Orpen, A.G. and Taylor, R. (1987)Tables of Bond Lengths determined by X-Ray and Neutron Diffraction. Part 1. Bond Lengths in Organic Compounds. Journal of the Chemical Society, Perkin Transactions, 2, S1-S19.
[26] Bertolasi, V., Gilli, P., Ferretti, V. and Gilli, G. (1993) Structure and Crystal Packing of the Antibacterial Drug 1-{[(5-Nitro-2-Furanyl)Methylene]Amino}-2,4-Imidazolidinedione (Nitrofurantoin). Acta Crystallographica Section C, 49, 741-744.
[27] Pienaar, E.W., Caira, M.R. and Lötter, A.P. (1993) Polymorphs of Nitrofurantoin. 2. Preparation and X-Ray Crystal Structures of Two Anhydrous Forms of Nitrofurantoin. Journal of Crystallographic and Spectroscopic Research, 23, 785-790.
[28] Vangala, V.R., Chow, P.S. and Tan, R.B.H. (2011) Characterization, Physicochemical and Photo-Stability of a Co-Crystal Involving an Antibiotic Drug, Nitrofurantoin, and 4-Hydroxybenzoic Acid. CrystEngComm, 13, 759-762.

Copyright © 2023 by authors and Scientific Research Publishing Inc.

Creative Commons License

This work and the related PDF file are licensed under a Creative Commons Attribution 4.0 International License.