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Structural Consequences of Anomeric Effect in 1,3,6,8-tetraazatricyclo[4.3.1.13,8]undecan-1-ium pentachlorophenolate monohydrate

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Abstract

The asymmetric unit of the crystal structure contains one molecule of the title compound and one molecule of water. X-ray diffraction spectrum of the ammonium salt of title compound exhibits deviations from the ideal molecular geometry which is explained on the basis of anomeric effect. This conclusion is consistent with the natural bond orbital analysis at the B3LYP/6-311+G** level of the anomeric effect. The molecules are linked via N–H···O hydrogen bonds. This compound crystallizes in monoclinic symmetry, in space group P2 1/n , with lattice constants: a = 12.3850(2) Å, b = 6.8123(1) Å, c = 19.6208(4) Å, α = 90°, β = 94.864(2)°, γ = 90°, V = 1649.45(5) Å3, Z = 4, F(000) = 896, R 1 = 3.3%, wR 2 = 10.6%.

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References

  1. Sobczyk L, Grabowski SJ, Krygowski TM (2005) Chem Rev 105:3513

    Article  CAS  Google Scholar 

  2. Mak TCW, Tse CS, Chong YH, Mok FC (1977) Acta Crystallogr B 33:2980

    Article  Google Scholar 

  3. Tse C-S, Wong Y-S, Mak TCW (1977) J Appl Cryst 10:68

    Article  Google Scholar 

  4. Ng SW, Hu SZ, Hanna JV, Raj SSS, Fun HK, Razak IA, Wojciechowski G, Brzezinski B (2001) J Mol Struct 595:189

    Article  CAS  Google Scholar 

  5. Ng SW, Naumov P, Drew MGB, Wojciechowski G, Brzezinski B (2001) J Mol Struct 595:29

    Article  CAS  Google Scholar 

  6. Ng SW, Naumov P, Ibrahim AR, Fun HK, Chantrapromma S, Wojciechowski G, Brzezinski B, Hanna JV (2002) J Mol Struct 609:89

    Article  CAS  Google Scholar 

  7. Ghosh K, Datta M, Fröhlich R, Ganguly NC (2005) J Mol Struct 737:201

    Article  CAS  Google Scholar 

  8. MacLean EJ, Glidewell C, Ferguson G, Gregson RM, Lough AJ (1999) Acta Crystallogr C 55:1870

    Article  Google Scholar 

  9. Jordan TH, Mak TCW (1970) J Chem Phys 52:3790

    Article  CAS  Google Scholar 

  10. Mak TCW, Li WK, Yip WH (1983) Acta Crystallogr C 39:134

    Article  Google Scholar 

  11. Rivera A, Nuñez ME, Morales-Ríos MS, Joseph-Nathan P (2004) Tetrahedron Lett 45:7563

    Article  CAS  Google Scholar 

  12. Rivera A, González-Salas D, Ríos-Motta J, Hernández-Barragán A, Joseph-Nathan P (2007) J Mol Struct 837:142

    Article  CAS  Google Scholar 

  13. Oxford Diffraction (2009) CrysAlis CCD & CrysAlis RED. Oxford Diffraction Ltd, Yarnton

    Google Scholar 

  14. Palatinus L, Chapuis G (2007) J Appl Cryst 40:786

    Article  CAS  Google Scholar 

  15. Petricek V, Dusek M, Palatinus L (2006) Jana2006. Structure Determination Software Programs. Institute of Physics, Praha

    Google Scholar 

  16. Becke AD (1988) Phys Rev A 38:3098

    Article  CAS  Google Scholar 

  17. Becke AD (1993) J Chem Phys 98:5648

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  19. Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Zakrzewski VG, Montgomery JA, Stratmann RE, Burant JC, Dapprich S, Millam JM, Daniels AD, Kudin KN, Strain MC, Farkas O, Tomasi J, Barone V, Cossi M, Cammi R, Mennucci B, Pomelli C, Adamo C, Clifford S, Ochterski J, Petersson GA, Ayala PY, Cui Q, Morokuma K, Malick DK, Rabuck AD, Raghavachari K, Foresman JB, Cioslowski J, Ortiz JV, Stefanov BB, Liu G, Liashenko A, Piskorz P, Komaromi I, Gomperts R, Martin RL, Fox DJ, Keith T, Al-Laham MA, Peng CY, Nanayakkara A, Gonzalez C, Challacombe M, Gill PMW, Johnson BG, Chen W, Wong MW, Andres JL, Head-Gordon M, Replogle ES, Pople JA (1998) Gaussian 98 (Revision A.9). Gaussian Inc, Pittsburgh

    Google Scholar 

  20. Rivera A, Gallo GI, Gayón ME, Joseph-Nathan P (1993) Synth Commun 23:2921

    Article  CAS  Google Scholar 

  21. Rivera A, Ríos-Motta J, Quevedo R, Joseph-Nathan P (2005) Rev Colomb Quim 34:105

    CAS  Google Scholar 

  22. Schreiber VM, Rospenk M, Kulbida AI, Sobczyk L (1997) Spectrochim Acta Part A 53:2067

    Article  Google Scholar 

  23. Alder RW, Carniero TMG, Mowlam RW, Orpen AG, Petillo PA, Vachon DJ, Weisman GR, White JM (1999) J Chem Soc Perkin Trans 2:589

    Google Scholar 

  24. Foster JP, Weinhold F (1980) J Am Chem Soc 102:7211

    Article  CAS  Google Scholar 

  25. Glendening ED, Reed AD, Carpenter JE, Weinhold F (1993) NBO Version 3.1. Theoretical Chemistry Institute, University of Wisconsin. Madison

    Google Scholar 

Download references

Acknowledgments

We acknowledge the Dirección de Investigaciones Sede Bogotá (DIB) of Universidad Nacional de Colombia for financial support and The Institutional Research Plan No. AVOZ10100521 of the Institute of Physics and the Project Praemium Academiae of the Academy of Sciences of the Czech Republic. Moreover, J. S–B. is also in debt to: The Faculty of Sciences of Universidad Nacional de Colombia for grating me a scholarship.

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Authors and Affiliations

  1. Departamento de Química, Universidad Nacional de Colombia, Ciudad Universitaria, Carrera 30 No. 45-03, Bogotá D.C., Colombia

    Augusto Rivera, John Sadat-Bernal & Jaime Ríos-Motta

  2. Institute of Physics, ASCR, v.v.i., Na Slovance 2, 182 21, Praha 8, Czech Republic

    Michal Dušek & Karla Fejfarová

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  1. Augusto Rivera
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  2. John Sadat-Bernal
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  3. Jaime Ríos-Motta
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  4. Michal Dušek
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  5. Karla Fejfarová
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Correspondence to Augusto Rivera.

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Rivera, A., Sadat-Bernal, J., Ríos-Motta, J. et al. Structural Consequences of Anomeric Effect in 1,3,6,8-tetraazatricyclo[4.3.1.13,8]undecan-1-ium pentachlorophenolate monohydrate. J Chem Crystallogr 41, 591–595 (2011). https://doi.org/10.1007/s10870-011-0008-8

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