cis-Diammine(glycolato-κO,O)platinum(II).

The reaction of cis-[Pt(NO(3))(2)(NH(3))(2)] and sodium glycolate yielded the title compound, [Pt(C(2)H(2)O(3))(NH(3))(2)]. The Pt(II) atom, coordinated by two N atoms of ammine and two O atoms of the carboxyl-ate and oxido groups of the glycolate ligand, is in a square-planar environment. In the crystal structure, mol-ecules are connected by inter-molecular N-H⋯O hydrogen bonds, forming a three-dimensional network.

Related literature

The title compound is a second-generation platinum derivative that has an anti­tumour activity comparable to that of cisplatin, one of the most effective anti-cancer drugs for testicular, lung, bladder and other carcinomas, but which is less toxic to the kidney, see: Inuyama et al. (1992 ▶); Kameyama et al. (1990 ▶); Noda et al. (1992 ▶); Taguchi et al. (1992 ▶); Yamamoto et al. (2000 ▶). For related structures, see: Yuge & Miyamoto (1998 ▶); Griffith et al. (2007 ▶).

Experimental

Crystal data

[Pt(C2H2O3)(NH3)2]

M = 303.19

Orthorhombic,

a = 5.6293 (6) Å

b = 7.2853 (8) Å

c = 14.1107 (16) Å

V = 578.70 (11) Å3

Z = 4

Mo Kα radiation

μ = 24.17 mm−1

T = 298 K

0.24 × 0.12 × 0.10 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2002 ▶) T min = 0.068, T max = 0.196

3739 measured reflections

1354 independent reflections

1307 reflections with I > 2σ(I)

R int = 0.034

Refinement

R[F 2 > 2σ(F 2)] = 0.020

wR(F 2) = 0.042

S = 0.99

1354 reflections

76 parameters

H-atom parameters constrained

Δρmax = 1.24 e Å−3

Δρmin = −1.10 e Å−3

Absolute structure: Flack (1983 ▶), 489 Friedel pairs

Flack parameter: 0.013 (17)

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809049757/rn2056sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809049757/rn2056Isup2.hkl

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

[Pt(C2H2O3)(NH3)2]	Dx = 3.480 Mg m−3
Mr = 303.19	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121	Cell parameters from 1354 reflections
a = 5.6293 (6) Å	θ = 2.9–28.3°
b = 7.2853 (8) Å	µ = 24.17 mm−1
c = 14.1107 (16) Å	T = 298 K
V = 578.70 (11) Å3	Block, colourless
Z = 4	0.24 × 0.12 × 0.10 mm
F(000) = 544

Bruker APEXII CCD area-detector diffractometer	1354 independent reflections
Radiation source: fine-focus sealed tube	1307 reflections with I > 2σ(I)
graphite	Rint = 0.034
phi and ω scans	θmax = 28.3°, θmin = 2.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 2002)	h = −6→7
Tmin = 0.068, Tmax = 0.196	k = −9→9
3739 measured reflections	l = −17→18

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.020	w = 1/[σ2(Fo2) + (0.0103P)2] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.042	(Δ/σ)max = 0.001
S = 0.99	Δρmax = 1.24 e Å−3
1354 reflections	Δρmin = −1.10 e Å−3
76 parameters	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
0 restraints	Extinction coefficient: 0.0087 (3)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), 489 Friedel pairs
Secondary atom site location: difference Fourier map	Flack parameter: 0.013 (17)

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'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 > σ(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	0.10734 (4)	0.96205 (3)	0.178777 (16)	0.01860 (9)
N2	0.0429 (10)	0.9713 (9)	0.3193 (4)	0.0310 (12)
H2A	0.1574	1.0347	0.3479	0.047*
H2B	0.0392	0.8577	0.3424	0.047*
H2C	−0.0964	1.0256	0.3296	0.047*
N1	0.4267 (10)	0.8432 (8)	0.2082 (3)	0.0272 (13)
H1A	0.4471	0.7457	0.1711	0.041*
H1B	0.4298	0.8085	0.2686	0.041*
H1C	0.5427	0.9237	0.1976	0.041*
O1	0.1557 (8)	0.9447 (7)	0.0377 (3)	0.0308 (11)
O2	−0.2005 (8)	1.0830 (7)	0.1425 (3)	0.0263 (11)
C1	−0.0264 (12)	0.9948 (9)	−0.0099 (4)	0.0230 (15)
C2	−0.2372 (12)	1.0639 (11)	0.0439 (5)	0.0332 (17)
H2E	−0.2827	1.1823	0.0182	0.040*
H2D	−0.3688	0.9803	0.0337	0.040*
O3	−0.0334 (8)	0.9898 (7)	−0.0983 (3)	0.0288 (11)

	U11	U22	U33	U12	U13	U23
Pt1	0.02166 (13)	0.02149 (13)	0.01266 (12)	−0.00028 (10)	−0.00029 (9)	0.00010 (9)
N2	0.030 (3)	0.043 (3)	0.020 (3)	0.003 (2)	0.001 (2)	−0.003 (3)
N1	0.033 (3)	0.036 (3)	0.012 (2)	0.010 (3)	0.005 (2)	0.003 (2)
O1	0.028 (3)	0.046 (3)	0.018 (2)	0.004 (2)	0.0023 (19)	−0.006 (2)
O2	0.027 (2)	0.038 (3)	0.014 (2)	0.008 (2)	−0.0030 (18)	−0.0067 (19)
C1	0.027 (3)	0.024 (4)	0.018 (3)	−0.003 (2)	0.003 (2)	0.003 (2)
C2	0.032 (4)	0.052 (5)	0.016 (3)	0.011 (3)	−0.002 (3)	−0.004 (3)
O3	0.036 (3)	0.038 (3)	0.012 (2)	−0.002 (2)	−0.0002 (18)	−0.0005 (19)

Pt1—O2	2.010 (5)	N1—H1B	0.8900
Pt1—O1	2.013 (4)	N1—H1C	0.8900
Pt1—N2	2.017 (5)	O1—C1	1.279 (8)
Pt1—N1	2.038 (5)	O2—C2	1.413 (7)
N2—H2A	0.8900	C1—O3	1.248 (8)
N2—H2B	0.8900	C1—C2	1.496 (9)
N2—H2C	0.8900	C2—H2E	0.9700
N1—H1A	0.8900	C2—H2D	0.9700
O2—Pt1—O1	83.82 (18)	Pt1—N1—H1C	109.5
O2—Pt1—N2	94.6 (2)	H1A—N1—H1C	109.5
O1—Pt1—N2	176.9 (2)	H1B—N1—H1C	109.5
O2—Pt1—N1	176.77 (19)	C1—O1—Pt1	113.2 (4)
O1—Pt1—N1	93.18 (18)	C2—O2—Pt1	109.5 (4)
N2—Pt1—N1	88.4 (2)	O3—C1—O1	122.8 (6)
Pt1—N2—H2A	109.5	O3—C1—C2	119.5 (6)
Pt1—N2—H2B	109.5	O1—C1—C2	117.7 (5)
H2A—N2—H2B	109.5	O2—C2—C1	114.7 (6)
Pt1—N2—H2C	109.5	O2—C2—H2E	108.6
H2A—N2—H2C	109.5	C1—C2—H2E	108.6
H2B—N2—H2C	109.5	O2—C2—H2D	108.6
Pt1—N1—H1A	109.5	C1—C2—H2D	108.6
Pt1—N1—H1B	109.5	H2E—C2—H2D	107.6
H1A—N1—H1B	109.5
O2—Pt1—O1—C1	−6.9 (4)	Pt1—O1—C1—O3	−178.2 (5)
N2—Pt1—O1—C1	53 (5)	Pt1—O1—C1—C2	2.4 (8)
N1—Pt1—O1—C1	174.3 (5)	Pt1—O2—C2—C1	−11.1 (7)
O1—Pt1—O2—C2	9.7 (4)	O3—C1—C2—O2	−173.3 (6)
N2—Pt1—O2—C2	−167.7 (5)	O1—C1—C2—O2	6.1 (10)
N1—Pt1—O2—C2	31 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1C···O2i	0.89	2.01	2.883 (8)	167
N1—H1B···O2ii	0.89	2.44	3.107 (7)	132
N1—H1B···O3iii	0.89	2.45	3.049 (7)	125
N1—H1A···O3iv	0.89	2.00	2.888 (7)	173
N2—H2C···O3v	0.89	2.32	3.108 (7)	147
N2—H2B···O2ii	0.89	2.21	3.014 (8)	150
N2—H2A···O3iii	0.89	2.26	3.010 (7)	142

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1C⋯O2i	0.89	2.01	2.883 (8)	167
N1—H1B⋯O2ii	0.89	2.44	3.107 (7)	132
N1—H1B⋯O3iii	0.89	2.45	3.049 (7)	125
N1—H1A⋯O3iv	0.89	2.00	2.888 (7)	173
N2—H2C⋯O3v	0.89	2.32	3.108 (7)	147
N2—H2B⋯O2ii	0.89	2.21	3.014 (8)	150
N2—H2A⋯O3iii	0.89	2.26	3.010 (7)	142

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