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Volume 65 
Part 2 
Pages o283-o284  
February 2009  

Received 12 November 2008
Accepted 5 January 2009
Online 10 January 2009

Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.007 Å
R = 0.043
wR = 0.116
Data-to-parameter ratio = 17.5
Details
Open access

Bis{(E)-3-[(diethylmethylammonio)methyl]-N-[3-(N,N-dimethylsulfamoyl)-1-methylpyridin-4-ylidene]-4-methoxyanilinium} tetraiodide pentahydrate

aiMed.UL, Faculty of Pharmacy, University of Lisbon, Av. Prof. Gama Pinto, 1649-003 Lisbon, Portugal, and bEd. CACTUS, Campus Sur, Unidade de Raios X, Universidad de Santiago Compostela 15782, Spain
Correspondence e-mail: fclopes@ff.ul.pt

The title compound, 2C21H34N4O3S2+·4I-·5H2O, was prepared exclusively as the E isomer by methylation of the corresponding N-phenylpyridin-4-amine. There are two symmetry-independent molecules in the asymmetric unit with no significant differences in bond lengths and angles. The aromatic rings are not coplanar with the pyridin-4-imine groups, as indicated by the C-N-C-C torsion angles of 47.7 (7) and 132.6 (5)°.

Related literature

For background information see: Bjorkman & Bhattarai (2005[Bjorkman, A. & Bhattarai, A. (2005). Acta Trop. 94, 163-169.]); Yeates et al. (2008[Yeates, C. L., Batchelor, J. F., Capon, E. C., Cheesman, N. J., Fry, M., Hudson, A. T., Pudney, M., Trimming, H., Woolven, J., Bueno, J. M., Chicharro, J., Fernández, E., Fiandor, J. M., Gargallo-Viola, D., de las Heras, F. G., Herreros, E. & León, M. L. (2008). J. Med. Chem. 51, 2845-2852.]). For related literature structures, see: Lopes et al. (2004[Lopes, F., Capela, R., Gonçalves, J. O., Horton, P. N., Hursthouse, M. B., Iley, J., Casimiro, C. M., Bom, J. & Moreira, R. (2004). Tetrahedron Lett. 45, 7663-7666.]); Wang et al. (2008[Wang, Y., Zhang, J., Chen, H. & Luo, S. (2008). Acta Cryst. E64, o1025.]); Djedouani et al. (2008[Djedouani, A., Boufas, S., Allain, M., Bouet, G. & Khan, M. (2008). Acta Cryst. E64, o1785.]).

[Scheme 1]

Experimental

Crystal data
  • 2C21H34N4O3S2+·4I-·5H2O

  • Mr = 1442.86

  • Triclinic, [P \overline 1]

  • a = 12.7930 (5) Å

  • b = 13.5539 (6) Å

  • c = 16.8386 (7) Å

  • [alpha] = 96.670 (2)°

  • [beta] = 97.667 (2)°

  • [gamma] = 98.224 (1)°

  • V = 2836.5 (2) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 2.33 mm-1

  • T = 100 (2) K

  • 0.35 × 0.2 × 0.08 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2005[Bruker (2005). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.575, Tmax = 0.830

  • 49577 measured reflections

  • 11468 independent reflections

  • 8753 reflections with I > 2[sigma](I)

  • Rint = 0.050

Refinement
  • R[F2 > 2[sigma](F2)] = 0.043

  • wR(F2) = 0.116

  • S = 1.00

  • 11468 reflections

  • 654 parameters

  • 17 restraints

  • H atoms treated by a mixture of independent and constrained refinement

  • [Delta][rho]max = 2.07 e Å-3

  • [Delta][rho]min = -1.42 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O1W-H1WA...I4 0.91 (3) 2.60 (4) 3.489 (4) 170 (3)
O1W-H1WB...I2 0.90 (2) 2.663 (17) 3.561 (4) 176 (4)
O2W-H2WA...O5wi 0.90 (4) 1.98 (5) 2.799 (7) 147 (5)
O2W-H2WB...I3 0.90 (4) 2.69 (4) 3.580 (5) 175 (4)
O3W-H3WA...O1Wi 0.90 (4) 1.91 (4) 2.781 (6) 161 (18)
O3W-H3WB...I1 0.90 (4) 2.64 (4) 3.544 (4) 178 (5)
O4W-H4WA...I4 0.90 (3) 2.75 (3) 3.613 (5) 160 (4)
O4W-H4WB...O3Wii 0.89 (5) 1.92 (4) 2.795 (7) 162 (2)
O5W-H5WA...I2 0.90 (4) 2.75 (5) 3.614 (5) 165 (4)
O5W-H5WB...O4wiii 0.90 (4) 1.94 (4) 2.809 (7) 161 (3)
N14-H14...O9 0.90 (3) 1.93 (4) 2.733 (5) 149 (4)
N54-H54...O49 0.90 (5) 2.08 (4) 2.767 (5) 133 (4)
Symmetry codes: (i) x, y+1, z; (ii) x, y-1, z; (iii) x+1, y, z.

Data collection: APEX2 (Bruker, 2005[Bruker (2005). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2005[Bruker (2005). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SIR97 (Altomare et al., 1999[Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115-119.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]); software used to prepare material for publication: WinGX (Farrugia, 1999[Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BG2227 ).


Acknowledgements

Intensity measurements were performed at the Unidade de Raios X, RIAIDT, University of Santiago de Compostela, SPAIN. This work was supported by Fundação para a Ciência e Tecnologia (FCT, Portugal); TR acknowledges the FCT for the PhD grant SFRH/BD/30689/2006.

References

Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115-119.  [ISI] [CrossRef] [ChemPort] [details]
Bjorkman, A. & Bhattarai, A. (2005). Acta Trop. 94, 163-169.  [PubMed]
Bruker (2005). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Djedouani, A., Boufas, S., Allain, M., Bouet, G. & Khan, M. (2008). Acta Cryst. E64, o1785.  [CSD] [CrossRef] [details]
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  [CrossRef] [details]
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.  [CrossRef] [ChemPort] [details]
Lopes, F., Capela, R., Gonçalves, J. O., Horton, P. N., Hursthouse, M. B., Iley, J., Casimiro, C. M., Bom, J. & Moreira, R. (2004). Tetrahedron Lett. 45, 7663-7666.  [ISI] [CSD] [CrossRef] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Wang, Y., Zhang, J., Chen, H. & Luo, S. (2008). Acta Cryst. E64, o1025.  [CSD] [CrossRef] [details]
Yeates, C. L., Batchelor, J. F., Capon, E. C., Cheesman, N. J., Fry, M., Hudson, A. T., Pudney, M., Trimming, H., Woolven, J., Bueno, J. M., Chicharro, J., Fernández, E., Fiandor, J. M., Gargallo-Viola, D., de las Heras, F. G., Herreros, E. & León, M. L. (2008). J. Med. Chem. 51, 2845-2852.  [ISI] [CrossRef] [PubMed] [ChemPort]


Acta Cryst (2009). E65, o283-o284   [ doi:10.1107/S1600536809000324 ]

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