N,N′-bis­[(3-hy­droxy-4(4H)-oxypyran-2-yl)meth­yl]-N,N′-dimethyl­ethylene-1,2-diammonium tetra­chloridoplatinate(II) dihydrate

Fusi, V.; Giorgi, L.; Macedi, E.; Paoli, P.; Rossi, P.

doi:10.1107/S1600536812040949

Volume 68
Part 11
Pages m1323-m1324
November 2012

Received 10 September 2012
Accepted 28 September 2012
Online 6 October 2012

Key indicators
Single-crystal X-ray study
T = 150 K
Mean (C-C) = 0.005 Å
R = 0.023
wR = 0.049
Data-to-parameter ratio = 17.2
Details

N,N'-bis[(3-hydroxy-4(4H)-oxypyran-2-yl)methyl]-N,N'-dimethylethylene-1,2-diammonium tetrachloridoplatinate(II) dihydrate

Vieri Fusi,^a Luca Giorgi,^a Eleonora Macedi,^b Paola Paoli ^b ^* and Patrizia Rossi ^b

^aDepartment of Basic Sciences and Fundamentals, University of Urbino, I-61029 Urbino, Italy, and ^bDip. Energetica `Sergio Stecco', University of Firenze, Via S. Marta 3, I-50139 Firenze, Italy
Correspondence e-mail: paolapaoli@unifi.it

The title compound (C₁₆H₂₂N₂O₆)[PtCl₄]·2H₂O, shows antiproliferative activity in eight tumor cell lines. The asymmetric unit consists of one solvent water molecule on a general position, and one half of each of the polyammonium cation and the tetrachloridoplatinate(II) anion, both of them located on centers of inversion. In the crystal, the cations are connected via hydrogen bonding between the carbonyl O atoms and the hydroxyl H atoms into zigzag chains that elongate in the c-axis direction. In addition, the carbonyl O atom is hydrogen-bonded to the water molecule which, in turn, interacts with the [PtCl₄]^2- anion. Finally, the chains are linked by N-H⁺Cl interactions into a three-dimensional network.

Related literature

For the antitumor activity of maltol (systematic name: 3-hydroxy-2-methyl-4-pyrone) and polyamines, see: Casero & Woster (2001); Liang et al. (2006); Murakami et al. (2006). For background to the synthesis, solution behaviour, structural properties and biological activity of N,N'-bis[(3-hydroxy-4-pyron-2-yl)methyl]-N,N'-dimethylethylendiamine (Malten), see: Amatori et al. (2010, 2012).

Experimental

Crystal data

(C₁₆H₂₂N₂O₆)[PtCl₄]·2H₂O
M_r = 711.28
Triclinic, $[P \overline 1]$
a = 6.4775 (4) Å
b = 7.0037 (4) Å
c = 13.1628 (8) Å
= 88.810 (5)°
= 87.033 (5)°
= 71.927 (6)°
V = 566.92 (6) Å³
Z = 1
Mo K radiation
= 6.71 mm^-1
T = 150 K
0.32 × 0.22 × 0.20 mm

Data collection

Oxford Diffraction Xcalibur3 diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction 2009 $[Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Abingdon, England.]$ ) T_min = 0.164, T_max = 0.262
9431 measured reflections
2719 independent reflections
2694 reflections with I > 2(I)
R_int = 0.044

Refinement

R[F² > 2(F²)] = 0.023
wR(F²) = 0.049
S = 1.02
2719 reflections
158 parameters
H atoms treated by a mixture of independent and constrained refinement
_max = 1.44 e Å^-3
_min = -1.14 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O1-H1OO2ⁱ	0.73 (4)	1.98 (4)	2.655 (4)	154 (4)
O1W-H1WBO2ⁱⁱ	0.79 (5)	2.07 (5)	2.853 (4)	171 (5)
O1W-H1WACl2	0.84 (5)	2.45 (5)	3.282 (3)	174 (5)
N1-H1NCl1ⁱⁱⁱ	0.74 (4)	2.79 (4)	3.380 (3)	139 (4)
N1-H1NCl1^iv	0.74 (4)	2.79 (4)	3.362 (3)	136 (4)
Symmetry codes: (i) -x+2, -y+1, -z; (ii) -x+2, -y, -z; (iii) -x+2, -y+1, -z+1; (iv) x-1, y+1, z.

Data collection: CrysAlis PRO (Oxford Diffraction 2009 $[Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Abingdon, England.]$ ); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: PARST97 (Nardelli, 1995).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: NC2294 ).

Acknowledgements

The authors acknowledge CRIST (Centro di Cristallografia Strutturale, University of Firenze), where the data collection was performed, and the Italian Ministero dell'Istruzione dell'Università e della Ricerca (MIUR), PRIN2009, for financial support.

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.
Amatori, S., Ambrosi, G., Fanelli, M., Formica, M., Fusi, V., Giorgi, L., Macedi, E., Micheloni, M., Paoli, P., Pontellini, R. & Rossi, P. (2012). J. Org. Chem. 77, 2207-2218.
Amatori, S., Bagaloni, I., Fanelli, M., Formica, M., Fusi, V., Giorgi, L. & Macedi, E. (2010). Br. J. Cancer, 103, 239-248.
Casero, R. A. J. & Woster, P. M. J. (2001). Med. Chem. 44, 1-26.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Liang, F., Wan, S., Li, Z., Xiong, X., Yang, L., Zhou, X. & Wu, C. (2006). Curr. Med. Chem. 13, 711-727.
Murakami, K., Ishida, K., Watakabe, K., Tsubouchi, R., Naruse, M. & Yoshino, M. (2006). Toxicol. Lett. 161, 102-107.
Nardelli, M. (1995). J. Appl. Cryst. 28, 659.
Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Abingdon, England.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.

metal-organic compounds