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Volume 69 
Part 7 
Pages o1019-o1020  
July 2013  

Received 16 May 2013
Accepted 29 May 2013
Online 8 June 2013

Key indicators
Single-crystal X-ray study
T = 200 K
Mean [sigma](C-C) = 0.005 Å
Some non-H atoms missing,
Disorder in main residue
R = 0.051
wR = 0.139
Data-to-parameter ratio = 15.8
Details
Open access

N,N,N-Trimethyl-N-(methyl 5-deoxy-2,3-O-isopropylidene-[beta]-D-ribofuranosid-5-yl)ammonium 4-methylbenzenesulfonate sesquihydrate

aDepartment of Chemistry, University of Gdansk, Sobieskiego 18, PL-80952 Gdansk, Poland,bDepartment of Chemistry, University of Gdansk, Sobieskiego 18, Gdansk, PL-80952, Poland, and cDepartment of Chemistry, Gdansk University of Technology, G. Narutowicza Str. 11/12, PL-80233 Gdansk, Poland
Correspondence e-mail: jaroslaw.chojnacki@pg.gda.pl

The structure of the title compound, [C12H24NO4][C7H7O3S]·1.5H2O, contains alternating layers parallel to (001) of hydrophobic and polar character, stabilized by C-H...O hydrogen bonding. The furan ring adopts an envelope conformation with the C(OMe) atom as the flap, and the dioxolane ring is twisted about one of the O-C(methine) bonds. A comparison to related compounds is presented. The tosylate-O atoms were disordered over two positions with the major component having a site occupancy factor = 0.566 (12). The structure was refined as a rotary twin with regard to rotation about the c axis with the contribution of the second component being 0.0048 (6). Solvate water molecules are highly disordered and were removed using the SQUEEZE procedure; the unit cell characteristics take into account the presence of the disordered solvent. High-resolution 1H and 13C NMR spectroscopic data are also presented.

Related literature

For background to quaternary ammonium compounds, see: Jones (1984[Jones, G. (1984). Pyridines and their Benzo Derivatives in Comprehensive Heterocyclic Chemistry, edited by A. R. Katrizky & C. W. Rees, Vol. 2, Part 2A, pp. 395-510. Oxford, New York, Toronto, Sydney, Paris, Frankfurt: Pergamon Press.]); Sliwa (1996[Sliwa, W. (1996). In N-Substituted Salts of Pyridine and Related Compounds. Monograph. Czestochowa, Poland: WSP.]); Sajomsang et al. (2009[Sajomsang, W., Tantayanon, S., Tangpasuthadol, V. & Daly, W. (2009). Carbohydr. Res. 344, 2502-2511.]); Oblak & Gamian (2010[Oblak, E. & Gamian, A. (2010). Adv. Hyg. Exp. Med. 64, 201-211.]); Binks et al. (2011[Binks, B. P., Fletcher, P. D., Salama, I. E., Horsup, D. I. & Moore, J. A. (2011). Langmuir, 27, 469-473.]); Singh et al. (2009[Singh, S., Bhadani, A., Kataria, H., Kaur, G. & Kamboj, R. (2009). Ind. Eng. Chem. Res. 48, 1673-1677.]); Cruz-Guzman et al. (2005[Cruz-Guzman, M., Celis, R., Hermosin, M. C., Koskinen, W. C. & Cornejo, J. (2005). J. Agric. Food Chem. 53, 7502-7511.]); Rabea et al. (2003[Rabea, E. I., Badawy, M. E., Stevens, C. V., Smagghe, G. & Steurbaut, W. (2003). Biomacromolecules, 4, 1457-1465.]); Belalia et al., 2008[Belalia, R., Grelier, S., Benaissa, M. & Coma, V. (2008). J. Agric. Food Chem. 56, 1582-1588.]; McDonnell & Russell (1999[McDonnell, G. & Russell, A. D. (1999). Clin. Microbiol. Rev. 12, 147-179.]); Boethling (1984[Boethling, R. S. (1984). Water Res. 18, 1061-1076.]); Levinson (1999[Levinson, M. I. (1999). J. Surfact. Deterg. 2, 223-235.]); Cross & Singer (1994[Cross, J. & Singer, E. J. (1994). In Cationic Surfactants. New York: Marcel Dekker Inc.]). For QAC sugar derivatives, see: Abel et al. (2002[Abel, T., Cohen, J. I., Engel, R., Filshtinskaya, M., Melkonian, A. & Melkonian, K. (2002). Carbohydr. Res. 337, 2495-2499.]); Blizzard et al. (2002[Blizzard, T. A., Kim, R. M., Morgan, J. D. II, Chang, J., Kohler, J., Kilburn, R., Chapman, K. & Hammond, M. L. (2002). Bioorg. Med. Chem. Lett. 12, 849-852.]); Honda et al. (1988[Honda, T., Kato, M., Inoue, M., Shimamoto, T., Shima, K., Nakanishi, T., Yoshida, T. & Noguchi, T. (1988). J. Med. Chem. 31, 1295-1305.]); Thomas et al. (2009[Thomas, M., Montenegro, D., Castano, A., Friedman, L., Leb, J., Huang, M. L., Rothman, L., Lee, H., Capodiferro, C., Ambinder, D., Cere, E., Galante, J., Rizzo, J., Melkonian, K. & Engel, R. (2009). Carbohydr. Res. 344, 1620-1627.]); Maslov et al. (2010[Maslov, M., Morozova, N., Chizhik, E., Rapoport, D., Ryabchikova, E., Zenkova, M. & Serebrennikova, G. (2010). Carbohydr. Res. 345, 2438-2449.]); Dmochowska et al. (2006[Dmochowska, B., Skorupa, E., Pellowska-Januszek, L., Czarkowska, M., Sikorski, A. & Wisniewski, A. (2006). Carbohydr. Res. 341, 1916-1921.], 2009[Dmochowska, B., Skorupa, E., Switecka, P., Sikorski, A., Lacka, I., Milewski, S. & Wisniewski, A. (2009). J. Carbohydr. Chem. 28, 222-233.], 2011[Dmochowska, B., Piosik, J., Woziwodzka, A., Sikora, K., Wisniewski, A. & Wegrzyn, G. (2011). J. Hazard. Mater. 193, 272-278.]); Pellowska-Januszek et al. (2004[Pellowska-Januszek, L., Dmochowska, B., Skorupa, E., Chojnacki, J., Wojnowski, W. & Wisniewski, A. (2004). Carbohydr. Res. 339, 1537-1544.]); Skorupa et al. (2004[Skorupa, E., Dmochowska, B., Pellowska-Januszek, L., Wojnowski, W., Chojnacki, J. & Wisniewski, A. (2004). Carbohydr. Res. 339, 2355-2362.]). For related synthetic methods, see: Gosh & Liu (1996[Gosh, A. K. & Liu, W. (1996). J. Org. Chem. 61, 6175-6182.]); Sairam et al. 2003[Sairam, P., Puranik, R., Rao, B. S., Swamy, P. V. & Chandra, S. (2003). Carbohydr. Res. 338, 303-306.]; Sarabia-Garcia & Lopez-Herrera (1996[Sarabia-Garcia, F. & Lopez-Herrera, F. J. (1996). Tetrahedron, 53, 4757-4768.]); Dibrov et al. (2010[Dibrov, S., Carnevali, M. & Hermann, T. (2010). Acta Cryst. E66, o3088.]). For ring puckering analysis, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]).

[Scheme 1]

Experimental

Crystal data
  • C12H24NO4+·C7H7O3S-·1.5H2O

  • Mr = 444.53

  • Monoclinic, P 21

  • a = 11.4896 (15) Å

  • b = 7.9311 (11) Å

  • c = 13.4853 (17) Å

  • [beta] = 111.619 (12)°

  • V = 1142.4 (3) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.19 mm-1

  • T = 200 K

  • 0.37 × 0.2 × 0.17 mm

Data collection
  • Kuma KM4CCD (Sapphire2 detector) diffractometer

  • 26053 measured reflections

  • 4481 independent reflections

  • 4325 reflections with I > 2[sigma](I)

  • Rint = 0.038

Refinement
  • R[F2 > 2[sigma](F2)] = 0.051

  • wR(F2) = 0.139

  • S = 1.07

  • 4481 reflections

  • 283 parameters

  • 40 restraints

  • H-atom parameters constrained

  • [Delta][rho]max = 0.40 e Å-3

  • [Delta][rho]min = -0.31 e Å-3

  • Absolute structure: Flack & Bernardinelli (1999[Flack, H. D. & Bernardinelli, G. (1999). Acta Cryst. A55, 908-915.])

  • Flack parameter: 0.08 (12)

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C13-H13A...O28Ai 0.98 2.45 3.412 (15) 167
C13-H13B...O28Aii 0.98 2.44 3.308 (13) 148
C14-H14B...O26Ai 0.98 2.30 3.251 (9) 163
C14-H14C...O27Aiii 0.98 2.22 3.161 (8) 162
C15-H15C...O5 0.98 2.41 2.964 (4) 115
C19-H19...O26A 0.95 2.26 2.712 (9) 108
Symmetry codes: (i) [-x+1, y+{\script{1\over 2}}, -z+1]; (ii) x, y+1, z; (iii) [-x+1, y+{\script{3\over 2}}, -z+1].

Data collection: CrysAlis CCD (Oxford Diffraction, 2006[Oxford Diffraction (2006). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.]); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2006[Oxford Diffraction (2006). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]) and WinGX (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); molecular graphics: Mercury (Macrae et al., 2006[Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.]); software used to prepare material for publication: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]) and publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: TK5228 ).


Acknowledgements

This work was partially financed by grant DS/530-8451-D193-13. We thank Ms Iwona Rabczuk for some of the experimental work and M. Sc. Leszek Lobocki for measurements of mass spectra (MALDI TOF).

References

Abel, T., Cohen, J. I., Engel, R., Filshtinskaya, M., Melkonian, A. & Melkonian, K. (2002). Carbohydr. Res. 337, 2495-2499.  [Web of Science] [CrossRef] [PubMed] [ChemPort]
Belalia, R., Grelier, S., Benaissa, M. & Coma, V. (2008). J. Agric. Food Chem. 56, 1582-1588.  [Web of Science] [CrossRef] [PubMed] [ChemPort]
Binks, B. P., Fletcher, P. D., Salama, I. E., Horsup, D. I. & Moore, J. A. (2011). Langmuir, 27, 469-473.  [Web of Science] [CrossRef] [ChemPort] [PubMed]
Blizzard, T. A., Kim, R. M., Morgan, J. D. II, Chang, J., Kohler, J., Kilburn, R., Chapman, K. & Hammond, M. L. (2002). Bioorg. Med. Chem. Lett. 12, 849-852.  [CrossRef] [PubMed] [ChemPort]
Boethling, R. S. (1984). Water Res. 18, 1061-1076.  [CrossRef] [ChemPort] [Web of Science]
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.  [CrossRef] [ChemPort] [Web of Science]
Cross, J. & Singer, E. J. (1994). In Cationic Surfactants. New York: Marcel Dekker Inc.
Cruz-Guzman, M., Celis, R., Hermosin, M. C., Koskinen, W. C. & Cornejo, J. (2005). J. Agric. Food Chem. 53, 7502-7511.  [Web of Science] [PubMed] [ChemPort]
Dibrov, S., Carnevali, M. & Hermann, T. (2010). Acta Cryst. E66, o3088.  [CSD] [CrossRef] [IUCr Journals]
Dmochowska, B., Piosik, J., Woziwodzka, A., Sikora, K., Wisniewski, A. & Wegrzyn, G. (2011). J. Hazard. Mater. 193, 272-278.  [Web of Science] [CrossRef] [ChemPort] [PubMed]
Dmochowska, B., Skorupa, E., Pellowska-Januszek, L., Czarkowska, M., Sikorski, A. & Wisniewski, A. (2006). Carbohydr. Res. 341, 1916-1921.  [Web of Science] [CSD] [CrossRef] [PubMed] [ChemPort]
Dmochowska, B., Skorupa, E., Switecka, P., Sikorski, A., Lacka, I., Milewski, S. & Wisniewski, A. (2009). J. Carbohydr. Chem. 28, 222-233.  [Web of Science] [CSD] [CrossRef] [ChemPort]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Flack, H. D. & Bernardinelli, G. (1999). Acta Cryst. A55, 908-915.  [CrossRef] [IUCr Journals]
Gosh, A. K. & Liu, W. (1996). J. Org. Chem. 61, 6175-6182.  [PubMed]
Honda, T., Kato, M., Inoue, M., Shimamoto, T., Shima, K., Nakanishi, T., Yoshida, T. & Noguchi, T. (1988). J. Med. Chem. 31, 1295-1305.  [CrossRef] [ChemPort] [PubMed] [Web of Science]
Jones, G. (1984). Pyridines and their Benzo Derivatives in Comprehensive Heterocyclic Chemistry, edited by A. R. Katrizky & C. W. Rees, Vol. 2, Part 2A, pp. 395-510. Oxford, New York, Toronto, Sydney, Paris, Frankfurt: Pergamon Press.
Levinson, M. I. (1999). J. Surfact. Deterg. 2, 223-235.  [CrossRef] [ChemPort]
Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Maslov, M., Morozova, N., Chizhik, E., Rapoport, D., Ryabchikova, E., Zenkova, M. & Serebrennikova, G. (2010). Carbohydr. Res. 345, 2438-2449.  [Web of Science] [CrossRef] [ChemPort] [PubMed]
McDonnell, G. & Russell, A. D. (1999). Clin. Microbiol. Rev. 12, 147-179.  [Web of Science] [ChemPort] [PubMed]
Oblak, E. & Gamian, A. (2010). Adv. Hyg. Exp. Med. 64, 201-211.
Oxford Diffraction (2006). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.
Pellowska-Januszek, L., Dmochowska, B., Skorupa, E., Chojnacki, J., Wojnowski, W. & Wisniewski, A. (2004). Carbohydr. Res. 339, 1537-1544.  [Web of Science] [PubMed] [ChemPort]
Rabea, E. I., Badawy, M. E., Stevens, C. V., Smagghe, G. & Steurbaut, W. (2003). Biomacromolecules, 4, 1457-1465.  [Web of Science] [CrossRef] [PubMed] [ChemPort]
Sairam, P., Puranik, R., Rao, B. S., Swamy, P. V. & Chandra, S. (2003). Carbohydr. Res. 338, 303-306.  [Web of Science] [CrossRef] [PubMed] [ChemPort]
Sajomsang, W., Tantayanon, S., Tangpasuthadol, V. & Daly, W. (2009). Carbohydr. Res. 344, 2502-2511.  [Web of Science] [CrossRef] [PubMed] [ChemPort]
Sarabia-Garcia, F. & Lopez-Herrera, F. J. (1996). Tetrahedron, 53, 4757-4768.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Singh, S., Bhadani, A., Kataria, H., Kaur, G. & Kamboj, R. (2009). Ind. Eng. Chem. Res. 48, 1673-1677.  [CrossRef] [ChemPort]
Skorupa, E., Dmochowska, B., Pellowska-Januszek, L., Wojnowski, W., Chojnacki, J. & Wisniewski, A. (2004). Carbohydr. Res. 339, 2355-2362.  [Web of Science] [CSD] [CrossRef] [PubMed] [ChemPort]
Sliwa, W. (1996). In N-Substituted Salts of Pyridine and Related Compounds. Monograph. Czestochowa, Poland: WSP.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Thomas, M., Montenegro, D., Castano, A., Friedman, L., Leb, J., Huang, M. L., Rothman, L., Lee, H., Capodiferro, C., Ambinder, D., Cere, E., Galante, J., Rizzo, J., Melkonian, K. & Engel, R. (2009). Carbohydr. Res. 344, 1620-1627.  [Web of Science] [CrossRef] [PubMed] [ChemPort]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]


Acta Cryst (2013). E69, o1019-o1020   [ doi:10.1107/S1600536813014797 ]

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