Received 14 January 2013
The title compound, 2C20H29N2O5S+·C6H8O42-·4H2O, which was found to be optically active, is a relatively rare example of a chiral compound crystallizing in the triclinic crystal system. The dihedral angles between the phenyl rings of the cations are 60.03 (15) and 62.03 (16)°, while the C atoms of the anion are almost coplanar (r.m.s. deviation 0.085 Å) and all trans to each other. In the crystal, the components are connected by an extensive network of N-HO and O-HO hydrogen bonds. The sulfonamide groups link the cations into pairs via two N-HO hydrogen bonds about the pseudo-inversion centre, leading to the formation of R22(8) rings. The anions are stacked in between four cationic pairs. Pairs of water molecules bridge the larger building units, forming hydrogen bonds with the remaining two O atoms of the anion.
(R)-5-(2-(2-(2-Ethoxyphenoxy)ethylamino)propyl)-2-methoxybenzenesulfonamide (generic name tamsulosin) has an -adrenergic blocking action and possesses hypotensive activity and is used mainly for the treatment of benign prostatic hyperplasia, see: Abrams et al. (1995).
Data collection: COLLECT (Nonius, 1998); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO-SMN; 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, 2012) and Mercury (Macrae et al., 2006); software used to prepare material for publication: publCIF (Westrip, 2010).
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LD2093 ).
The financial support of Ministry of Education, Science, Culture and Sport of the Republic of Slovenia via grant X-2000 is acknowledged.
Abrams, P., Schulman, C. C., Vaage, S. & Wyndaele, J. (1995). Br. J. Urol. 76, 325-336.
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.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.
Flack, H. D. (1983). Acta Cryst. A39, 876-881.
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.
Nonius (1998). COLLECT. Nonius BV, Delft, The Netherlands.
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.