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

Rodrigues, T.; Moreira, R.; Dacunha-Marinho, B.; Lopes, F.

doi:10.1107/S1600536809000324

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 (C-C) = 0.007 Å
R = 0.043
wR = 0.116
Data-to-parameter ratio = 17.5
Details

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

Tiago Rodrigues,^a Rui Moreira,^a Bruno Dacunha-Marinho ^b and Francisca Lopes ^a ^*

^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); Yeates et al. (2008). For related literature structures, see: Lopes et al. (2004); Wang et al. (2008); Djedouani et al. (2008).

Experimental

Crystal data

2C₂₁H₃₄N₄O₃S²⁺·4I^-·5H₂O
M_r = 1442.86
Triclinic, $[P \overline 1]$
a = 12.7930 (5) Å
b = 13.5539 (6) Å
c = 16.8386 (7) Å
= 96.670 (2)°
= 97.667 (2)°
= 98.224 (1)°
V = 2836.5 (2) Å³
Z = 2
Mo K radiation
= 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) T_min = 0.575, T_max = 0.830
49577 measured reflections
11468 independent reflections
8753 reflections with I > 2(I)
R_int = 0.050

Refinement

R[F² > 2(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
_max = 2.07 e Å^-3
_min = -1.42 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O1W-H1WAI4	0.91 (3)	2.60 (4)	3.489 (4)	170 (3)
O1W-H1WBI2	0.90 (2)	2.663 (17)	3.561 (4)	176 (4)
O2W-H2WAO5wⁱ	0.90 (4)	1.98 (5)	2.799 (7)	147 (5)
O2W-H2WBI3	0.90 (4)	2.69 (4)	3.580 (5)	175 (4)
O3W-H3WAO1Wⁱ	0.90 (4)	1.91 (4)	2.781 (6)	161 (18)
O3W-H3WBI1	0.90 (4)	2.64 (4)	3.544 (4)	178 (5)
O4W-H4WAI4	0.90 (3)	2.75 (3)	3.613 (5)	160 (4)
O4W-H4WBO3Wⁱⁱ	0.89 (5)	1.92 (4)	2.795 (7)	162 (2)
O5W-H5WAI2	0.90 (4)	2.75 (5)	3.614 (5)	165 (4)
O5W-H5WBO4wⁱⁱⁱ	0.90 (4)	1.94 (4)	2.809 (7)	161 (3)
N14-H14O9	0.90 (3)	1.93 (4)	2.733 (5)	149 (4)
N54-H54O49	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); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT; program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

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.
Bjorkman, A. & Bhattarai, A. (2005). Acta Trop. 94, 163-169.
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.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.
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.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Wang, Y., Zhang, J., Chen, H. & Luo, S. (2008). Acta Cryst. E64, o1025.
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.

organic compounds