Abstract
A V-shape diquinoline was synthesized so that it used nitro groups as alternative sensor groups to the halogens employed previously. The solid-state structure of its inclusion compound with formic acid was carefully investigated in term of crystal engineering and supramolecular chemistry. A ternary inclusion complex was obtained and its supramolecular interactions were carefully investigated and presented. The suitable X-ray crystals were obtained by crystallization of the host diquinoline from formic acid. The structure adopted acid⋯pyridine hydrogen-bonded cocrystal in addition to other non-covalent interactions. No proton-transfer process was detected; no salt formation.
Graphical Abstract
A V-shape diquinoline was synthesized so that it used nitro groups as alternative sensor groups to the halogens employed previously. The solid-state structure of its inclusion compound with formic acid was carefully investigated in term of crystal engineering and supramolecular chemistry. A ternary inclusion complex was obtained and its supramolecular interactions were carefully investigated and presented. The suitable X-ray crystals were obtained by crystallization of the host diquinoline from formic acid (Figure 1).
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References
Atwood JL, Davies JED, MacNicol DD (eds) (1984) Inclusion compounds, vols 1–3. Academic Press, London
Atwood JL, Davies JED, MacNicol DD (eds) (1991) Inclusion compounds, vols 4–5. Oxford University Press, Oxford
MacNicol DD, Toda F, Bishop R (eds) (1996) Comprehensive supramolecular chemistry, vol 6, solid-state supramolecular chemistry: crystal engineering. Pergamon Press, Oxford
Jeffrey GA, Saenger W (1994) Hydrogen bonding in biological structures. Springer, Berlin
Desiraju GR (1989) Crystal engineering: the design of organic solids. Elsevier, Amsterdam
Desiraju GR, Steiner T (1999) The weak hydrogen bond in structural chemistry and biology. Oxford Science Publications, Oxford
Desiraju GR (1995) Angew Chem Int Ed Engl 34:2311
Desiraju GR, Gavezzotti A (1989) Acta Crystallogr B 45:473
Hunter CA, Lawson KR, Perkins J, Urch CJ (2001) J Chem Soc Perkin Trans 2:651
Suezawa H, Yoshida T, Hirota M, Takahashi H, Umezawa Y, Honda K, Tsuboyama S, Nishio M (2001) J Chem Soc Perkin Trans 2:651
Marjo CE, Bishop R, Craig DC, O’Brien A, Scudder ML (1994) J Chem Soc Chem Commun 2513
Alshahateet SF, Ong TT, Bishop R, Kooli F, Messali M (2006) Cryst Growth Des 6(7):1676
Alshahateet SF (2008) Mol Cryst Liq Cryst 493:95
Alshahateet SF, Bishop R, Craig DC, Scudder ML (2003) CrystEngComm 5:417
Bishop R, Scudder ML, Craig DC, Rahman ANMM, Alshahateet SF (2003) Mol Cryst Liq Cryst 440:173
Alshahateet SF, Bishop R, Scudder ML, Hu CY, Lau EHE, Kooli F, Judeh ZM, Tan RBH (2005) CrystEngComm 7:139
Alshahateet SF, Bishop R, Craig DC, Kooli F, Scudder ML (2008) CrystEngComm 10(3):297
Alshahateet SF, Bishop R, Craig DC, Scudder ML (2010) Cryst Growth Des 10:1842
Shattock TR, Arora KK, Vishweshwar P, Zaworotko MJ (2008) Cryst Growth Des 8(12):4533
Cheng C-C, Yan S-J (1982) Org React 28:37
Thummel RP (1992) Synlett 1–2
Bertz SH (1985) J Org Chem 50:3585
Bernstein J, Dunitz JD, Gavezzotti A (2008) Cryst Growth Des 8(6):2011
Boenigk D, Mootz J (1998) J Am Chem Soc 110:2135
Cowan JA, Howard JAK, Mclntyre GJ, Lo SM-F, Williams ID (2003) Acta Crystallogr B 59:794
Bis JA, Zaworotko MJ (2005) Cryst Growth Des 5(3):1169
Alghezawi NM, Alshahateet SF, Bishop R (2010) JJC 5(3):211–220
Weyna DR, Shattock TR, Vishweshwar P, Zaworotko MJ (2009) Cryst Growth Des 9(2):1106–1123
Johnson SL, Rumon KA (1965) J Phys Chem 69:74
Childs SL, Stahly GP, Park A (2007) Mol Pharm 4:323
Rae AD (2000) RAELS: a comprehensive least squares refinement program. Australian National University, Canberra
Acknowledgments
The author thanks Mutah University for support needed to finish this work. Special thanks to Prof. Koh Lip Lin and Ms. Geok Kheng Tan (the National University of Singapore) for running the X-ray experiments. Great thanks are due to Dr. Zaher Juddeh (National University of Singapore) for running some of the characterization experiments reported here.
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Alshahateet, S.F. Synthesis and X-Ray Crystallographic Analyses of a Ternary Inclusion Complex of Racemic V-Shaped Diheteroaromatic Host with Formic Acid and Water. J Chem Crystallogr 41, 570–576 (2011). https://doi.org/10.1007/s10870-010-9924-2
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DOI: https://doi.org/10.1007/s10870-010-9924-2