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

metal-organic compounds

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ISSN: 2056-9890

Volume 68| Part 11| November 2012| Pages m1323-m1324

doi:10.1107/S1600536812040949

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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

(Received 10 September 2012; accepted 28 September 2012; online 6 October 2012)

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
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 $[Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Abingdon, England.]$ ) T_min = 0.164, T_max = 0.262
9431 measured reflections
2719 independent reflections
2694 reflections with I > 2σ(I)
R_int = 0.044

Refinement

R[F² > 2σ(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
Δρ_max = 1.44 e Å⁻³
Δρ_min = −1.14 e Å⁻³

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⋯Cl1^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 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812040949/nc2294sup1.cif

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

checkCIF report

Comment top

Maltol (3-hydroxy-2-methyl-4-pyrone) is a natural compound, which exhibits interesting antineoplastic activities (Murakami et al., 2006). At the same time, linear polyamines are also known antitumor agents (Liang et al., 2006; Casero & Woster, 2001). For these reasons we synthesized and studied compound N,N'-bis((3-hydroxy-4-pyron-2-yl)methyl)-N,N'-dimethylethylendiamine (Malten) coupling two Maltol units to an aliphatic diamine. Malten has shown antiproliferative activity in eight tumor cell lines (Amatori et al.,2010; Amatori et al., 2012). In the asymmetric unit of the title compound half of the polyammonium cation [H₂Malten]²⁺ and of the tetrachloroplatinate(II) counterion are present, together with a crystallization water molecule. The two halves of each ion are related by a center of symmetry (Fig. 1). The [H₂Malten]²⁺ polyammonium chain, which joins the two aromatic rings, has an all-trans conformation and defines a plane which forms an angle of 65.4 (2)° with each of them. In the crystal lattice the [H₂Malten]²⁺ cations are each linked by two pairs of complementary O—H···O hydrogen bonds into centrosymmetric dimers, which are further linked into chains along the c axis (Fig. 2 and Table 1). Moreover, the carbonyl O atom (O2) is H-bonded to the lattice water molecule, which is also linked to the (PtCl₄)^2- anion by O—H···Cl interactions. Finally, the cations and anions are linked by N—H⁺···Cl interactions.

Related literature top

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 top

Malten^.2HClO₄ was dissolved in H₂O, K₂PtCl₄ was added and the pH adjusted to 3. Crystals suitable for X-ray analysis formed in one day at room temperature.

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction 2009); cell refinement: CrysAlis PRO (Oxford Diffraction 2009); data reduction: CrysAlis PRO (Oxford Diffraction 2009); 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).

Figures top

	Fig. 1. Crystal structure of the title compound with labelling and displacement ellipsoids drawn at the 30% probability level. Symmetry codes: i) = -x + 2, -y, -z + 1; ii) = -x + 1, -y + 1, -z + 1.
	Fig. 2. Crystal structure of the title compound with view along the a axis. Intermolecular hydrogen bonding is shown as dashed lines.

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

Crystal data top

(C₁₆H₂₂N₂O₆)[PtCl₄]·2H₂O	Z = 1
M_r = 711.28	F(000) = 346
Triclinic, P1	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0253P)²] where P = (F_o² + 2F_c²)/3
2719 reflections	(Δ/σ)_max < 0.001
158 parameters	Δρ_max = 1.44 e Å⁻³
0 restraints	Δρ_min = −1.14 e Å⁻³

Crystal data top

(C₁₆H₂₂N₂O₆)[PtCl₄]·2H₂O	γ = 71.927 (6)°
M_r = 711.28	V = 566.92 (6) Å³
Triclinic, P1	Z = 1
a = 6.4775 (4) Å	Mo Kα radiation
b = 7.0037 (4) Å	µ = 6.71 mm⁻¹
c = 13.1628 (8) Å	T = 150 K
α = 88.810 (5)°	0.32 × 0.22 × 0.20 mm
β = 87.033 (5)°

Data collection top

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

Refinement top

R[F² > 2σ(F²)] = 0.023	0 restraints
wR(F²) = 0.049	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	Δρ_max = 1.44 e Å⁻³
2719 reflections	Δρ_min = −1.14 e Å⁻³
158 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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)*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Symmetry codes: (i) −x+2, −y, −z+1; (ii) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

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···O2^iv	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···Cl1^v	0.74 (4)	2.79 (4)	3.380 (3)	139 (4)
N1—H1N···Cl1^vi	0.74 (4)	2.79 (4)	3.362 (3)	136 (4)

Symmetry codes: (iii) −x+2, −y+1, −z; (iv) −x+2, −y, −z; (v) −x+2, −y+1, −z+1; (vi) x−1, y+1, z.

Experimental details

Crystal data
Chemical formula	(C₁₆H₂₂N₂O₆)[PtCl₄]·2H₂O
M_r	711.28
Crystal system, space group	Triclinic, P1
Temperature (K)	150
a, b, c (Å)	6.4775 (4), 7.0037 (4), 13.1628 (8)
α, β, γ (°)	88.810 (5), 87.033 (5), 71.927 (6)
V (Å³)	566.92 (6)
Z	1
Radiation type	Mo Kα
µ (mm⁻¹)	6.71
Crystal size (mm)	0.32 × 0.22 × 0.20

Data collection
Diffractometer	Oxford Diffraction Xcalibur3 diffractometer
Absorption correction	Multi-scan (CrysAlis PRO; Oxford Diffraction 2009)
T_min, T_max	0.164, 0.262
No. of measured, independent and observed [I > 2σ(I)] reflections	9431, 2719, 2694
R_int	0.044
(sin θ/λ)_max (Å⁻¹)	0.689

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.023, 0.049, 1.02
No. of reflections	2719
No. of parameters	158
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	1.44, −1.14

Computer programs: CrysAlis PRO (Oxford Diffraction 2009), SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), PARST97 (Nardelli, 1995).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O···O2ⁱ	0.727 (38)	1.983 (43)	2.655 (4)	154 (4)
O1W—H1WB···O2ⁱⁱ	0.794 (51)	2.066 (50)	2.853 (4)	171 (4)
O1W—H1WA···Cl2	0.837 (52)	2.449 (51)	3.282 (3)	174 (5)
N1—H1N···Cl1ⁱⁱⁱ	0.743 (42)	2.786 (43)	3.380 (3)	139 (4)
N1—H1N···Cl1^iv	0.743 (42)	2.788 (36)	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.

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. Web of Science CrossRef CAS IUCr Journals Google Scholar
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ISSN: 2056-9890

Volume 68| Part 11| November 2012| Pages m1323-m1324

doi:10.1107/S1600536812040949

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metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

metal-organic compounds

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