N,N'-bis-[(3-hy-droxy-4(4H)-oxypyran-2-yl)meth-yl]-N,N'-dimethyl-ethylene-1,2-diammonium tetra-chloridoplatinate(II) dihydrate.

The title compound (C(16)H(22)N(2)O(6))[PtCl(4)]·2H(2)O, shows anti-proliferative activity in eight tumor cell lines. The asymmetric unit consists of one solvent water mol-ecule 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 mol-ecule which, in turn, inter-acts with the [PtCl(4)](2-) anion. Finally, the chains are linked by N-H(+)⋯Cl inter-actions 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 = 711.28

Triclinic,

a = 6.4775 (4) Å

b = 7.0037 (4) Å

c = 13.1628 (8) Å

α = 88.810 (5)°

β = 87.033 (5)°

γ = 71.927 (6)°

V = 566.92 (6) Å3

Z = 1

Mo Kα radiation

μ = 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 ▶) T min = 0.164, T max = 0.262

9431 measured reflections

2719 independent reflections

2694 reflections with I > 2σ(I)

R int = 0.044

Refinement

R[F 2 > 2σ(F 2)] = 0.023

wR(F 2) = 0.049

S = 1.02

2719 reflections

158 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 1.44 e Å−3

Δρmin = −1.14 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction 2009 ▶); 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 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812040949/nc2294sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812040949/nc2294Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

(C16H22N2O6)[PtCl4]·2H2O	Z = 1
Mr = 711.28	F(000) = 346
Triclinic, P1	Dx = 2.083 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.4775 (4) Å	Cell parameters from 7279 reflections
b = 7.0037 (4) Å	θ = 4.1–29.2°
c = 13.1628 (8) Å	µ = 6.71 mm−1
α = 88.810 (5)°	T = 150 K
β = 87.033 (5)°	Prismatic, light yellow
γ = 71.927 (6)°	0.32 × 0.22 × 0.20 mm
V = 566.92 (6) Å3

Oxford Diffraction Xcalibur3 diffractometer	2719 independent reflections
Radiation source: Enhance (Mo) X-ray Source	2694 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.044
Detector resolution: 16.4547 pixels mm-1	θmax = 29.3°, θmin = 4.1°
ω scans	h = −8→8
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction 2009)	k = −9→9
Tmin = 0.164, Tmax = 0.262	l = −17→17
9431 measured reflections

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.023	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.049	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ2(Fo2) + (0.0253P)2] where P = (Fo2 + 2Fc2)/3
2719 reflections	(Δ/σ)max < 0.001
158 parameters	Δρmax = 1.44 e Å−3
0 restraints	Δρmin = −1.14 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > 2σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq
Pt1	1.0000	0.0000	0.5000	0.01531 (6)
Cl1	1.25762 (12)	0.12554 (11)	0.42237 (6)	0.01926 (15)
Cl2	0.82520 (13)	0.02992 (11)	0.34889 (6)	0.02098 (16)
O1	0.8029 (5)	0.6477 (4)	0.1284 (2)	0.0298 (6)
O2	0.8598 (4)	0.3386 (4)	−0.00821 (17)	0.0278 (5)
O3	0.3953 (4)	0.4312 (3)	0.22157 (16)	0.0218 (5)
N1	0.5757 (4)	0.6487 (4)	0.3876 (2)	0.0169 (5)
C1	0.4294 (6)	0.2757 (5)	0.1565 (3)	0.0261 (7)
H1	0.3424	0.1924	0.1649	0.031*
C2	0.5823 (6)	0.2365 (5)	0.0809 (3)	0.0263 (7)
H2	0.5998	0.1263	0.0394	0.032*
C3	0.7197 (5)	0.3601 (5)	0.0625 (2)	0.0224 (7)
C4	0.6815 (5)	0.5228 (5)	0.1358 (2)	0.0205 (6)
C5	0.5256 (5)	0.5510 (5)	0.2108 (2)	0.0187 (6)
C6	0.4731 (5)	0.7161 (5)	0.2869 (2)	0.0190 (6)
H6A	0.3166	0.7682	0.2984	0.023*
H6B	0.5233	0.8244	0.2595	0.023*
C7	0.4568 (5)	0.5266 (5)	0.4470 (2)	0.0181 (6)
H7A	0.4719	0.4039	0.4103	0.022*
H7B	0.3033	0.6018	0.4532	0.022*
C15	0.8152 (5)	0.5442 (5)	0.3735 (2)	0.0181 (6)
H15A	0.8821	0.6290	0.3351	0.027*
H15B	0.8389	0.4207	0.3376	0.027*
H15C	0.8778	0.5159	0.4388	0.027*
O1W	1.1440 (5)	−0.0251 (4)	0.1423 (2)	0.0343 (6)
H1N	0.559 (6)	0.742 (6)	0.417 (3)	0.028 (11)*
H1O	0.888 (7)	0.623 (6)	0.088 (3)	0.024 (11)*
H1WA	1.062 (9)	−0.020 (8)	0.194 (4)	0.059 (16)*
H1WB	1.128 (7)	−0.105 (7)	0.104 (3)	0.040 (13)*

	U11	U22	U33	U12	U13	U23
Pt1	0.01339 (9)	0.01279 (9)	0.02021 (9)	−0.00476 (6)	0.00072 (6)	−0.00306 (6)
Cl1	0.0169 (4)	0.0185 (4)	0.0241 (4)	−0.0084 (3)	0.0032 (3)	−0.0031 (3)
Cl2	0.0223 (4)	0.0208 (4)	0.0219 (4)	−0.0092 (3)	−0.0040 (3)	−0.0009 (3)
O1	0.0347 (15)	0.0327 (14)	0.0275 (13)	−0.0200 (12)	0.0137 (12)	−0.0108 (11)
O2	0.0310 (14)	0.0309 (13)	0.0237 (12)	−0.0136 (11)	0.0074 (10)	−0.0087 (10)
O3	0.0236 (12)	0.0246 (12)	0.0197 (11)	−0.0112 (10)	−0.0005 (9)	−0.0021 (9)
N1	0.0197 (14)	0.0154 (13)	0.0168 (12)	−0.0074 (11)	0.0002 (10)	−0.0020 (10)
C1	0.0284 (19)	0.0261 (18)	0.0283 (17)	−0.0143 (15)	−0.0056 (15)	0.0001 (14)
C2	0.0310 (19)	0.0242 (17)	0.0271 (17)	−0.0134 (15)	0.0003 (15)	−0.0062 (13)
C3	0.0251 (18)	0.0222 (16)	0.0196 (15)	−0.0064 (13)	−0.0035 (13)	−0.0020 (12)
C4	0.0236 (17)	0.0208 (16)	0.0191 (15)	−0.0096 (13)	−0.0003 (13)	−0.0030 (12)
C5	0.0218 (16)	0.0177 (15)	0.0172 (14)	−0.0065 (13)	−0.0041 (13)	0.0014 (11)
C6	0.0220 (16)	0.0170 (15)	0.0170 (14)	−0.0047 (12)	−0.0027 (12)	0.0018 (11)
C7	0.0171 (15)	0.0176 (15)	0.0200 (15)	−0.0060 (12)	0.0006 (12)	0.0009 (11)
C15	0.0158 (15)	0.0189 (15)	0.0194 (14)	−0.0051 (12)	0.0007 (12)	−0.0008 (11)
O1W	0.0380 (17)	0.0383 (16)	0.0315 (15)	−0.0187 (13)	−0.0001 (13)	−0.0064 (12)

Pt1—Cl1i	2.3018 (8)	C2—C3	1.431 (5)
Pt1—Cl1	2.3018 (8)	C2—H2	0.9300
Pt1—Cl2i	2.3132 (7)	C3—C4	1.462 (4)
Pt1—Cl2	2.3132 (7)	C4—C5	1.348 (5)
O1—C4	1.345 (4)	C5—C6	1.491 (4)
O1—H1O	0.73 (4)	C6—H6A	0.9700
O2—C3	1.243 (4)	C6—H6B	0.9700
O3—C1	1.356 (4)	C7—C7ii	1.526 (6)
O3—C5	1.363 (4)	C7—H7A	0.9700
N1—C15	1.499 (4)	C7—H7B	0.9700
N1—C7	1.501 (4)	C15—H15A	0.9600
N1—C6	1.514 (4)	C15—H15B	0.9600
N1—H1N	0.74 (4)	C15—H15C	0.9600
C1—C2	1.337 (5)	O1W—H1WA	0.84 (5)
C1—H1	0.9300	O1W—H1WB	0.79 (5)
Cl1i—Pt1—Cl1	180.00 (4)	O1—C4—C3	119.7 (3)
Cl1i—Pt1—Cl2i	90.28 (3)	C5—C4—C3	121.2 (3)
Cl1—Pt1—Cl2i	89.72 (3)	C4—C5—O3	121.9 (3)
Cl1i—Pt1—Cl2	89.72 (3)	C4—C5—C6	124.4 (3)
Cl1—Pt1—Cl2	90.28 (3)	O3—C5—C6	113.7 (3)
Cl2i—Pt1—Cl2	180.0	C5—C6—N1	112.9 (2)
C4—O1—H1O	115 (3)	C5—C6—H6A	109.0
C1—O3—C5	118.6 (3)	N1—C6—H6A	109.0
C15—N1—C7	113.3 (2)	C5—C6—H6B	109.0
C15—N1—C6	111.5 (2)	N1—C6—H6B	109.0
C7—N1—C6	110.8 (2)	H6A—C6—H6B	107.8
C15—N1—H1N	109 (3)	N1—C7—C7ii	111.9 (3)
C7—N1—H1N	107 (3)	N1—C7—H7A	109.2
C6—N1—H1N	106 (3)	C7ii—C7—H7A	109.2
C2—C1—O3	123.1 (3)	N1—C7—H7B	109.2
C2—C1—H1	118.5	C7ii—C7—H7B	109.2
O3—C1—H1	118.5	H7A—C7—H7B	107.9
C1—C2—C3	121.5 (3)	N1—C15—H15A	109.5
C1—C2—H2	119.2	N1—C15—H15B	109.5
C3—C2—H2	119.2	H15A—C15—H15B	109.5
O2—C3—C2	125.6 (3)	N1—C15—H15C	109.5
O2—C3—C4	120.7 (3)	H15A—C15—H15C	109.5
C2—C3—C4	113.7 (3)	H15B—C15—H15C	109.5
O1—C4—C5	119.1 (3)	H1WA—O1W—H1WB	109 (5)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O···O2iii	0.73 (4)	1.98 (4)	2.655 (4)	154 (4)
O1W—H1WB···O2iv	0.79 (5)	2.07 (5)	2.853 (4)	171 (4)
O1W—H1WA···Cl2	0.84 (5)	2.45 (5)	3.282 (3)	174 (5)
N1—H1N···Cl1v	0.74 (4)	2.79 (4)	3.380 (3)	139 (4)
N1—H1N···Cl1vi	0.74 (4)	2.79 (4)	3.362 (3)	136 (4)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1O⋯O2i	0.73 (4)	1.98 (4)	2.655 (4)	154 (4)
O1W—H1WB⋯O2ii	0.79 (5)	2.07 (5)	2.853 (4)	171 (5)
O1W—H1WA⋯Cl2	0.84 (5)	2.45 (5)	3.282 (3)	174 (5)
N1—H1N⋯Cl1iii	0.74 (4)	2.79 (4)	3.380 (3)	139 (4)
N1—H1N⋯Cl1iv	0.74 (4)	2.79 (4)	3.362 (3)	136 (4)

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .