Linkage isomerism of organoplatinum(II) compounds coordinated by two 1,3-di­methyl­barbiturate anions

In two linkage isomers, bis[1,3-di­methyl-2,4,6(1H,3H,5H)-pyrimidine­trionato]-C⁵,O⁴-(ethyl­enedi­amine-N,N')platinum(II), [Pt(C₆H₇N₂O₃)₂(C₂H₈N₂)], (I), and bis[1,3-di­methyl-2,4,6(1H,3H,5H)-py­rim­idine­tri­on­ato-C⁵](ethyl­enediamine-N,N')­plati­num(II) di­hyd­rate, [Pt(C₆H₇N₂O₃)₂(C₂H₈N₂)]·2H₂O, (II), crystal­lized from the same aqueous solution containing [Pt(en)(OH)₂] and 1,3-di­methyl­barbituric acid (Hdmbarb) in a 1:2 molar ratio, a pair of monodentate dmbarb^- anions coordinate to the Pt atom at tetrahedral C atoms for (II), while one dmbarb^- anion coordinates at the carbon and the other at a deprotonated enol oxy­gen for (I). The Pt-C distances in (I) and (II) are comparable: 2.112 (4) Å for (I), and 2.114 (4) and 2.117 (4) Å for (II).

S1. Comment

Some water-soluble palladium(II) and platinum(II) complexes involved with ambidentate β-diketonate have been known as organometallic compounds, in those the monodentate β-diketonato ligand is bound to the Pd or Pt atoms at a central C atom, e.g. K[PtCl(acac-C)(acac-O,O')] (Hacac = 2,4-pentanedione) (Mason, Robertson & Pauling, 1969). By using a cyclic β-diketone, 1,3-cyclohexanedione (Hchdo), in place of ambidentate Hacac, we have recently reported the monoalkylplatinum(II) compound [Pt(en)(chdo-C)(chdo-O)]·3H₂O (3) (en = 1,2-diaminoethane), crystallized from a solution containing a 1:2 molar ratio of [Pt(en)(OH)₂] and Hchdo (Yuge & Miyamoto, 1999); two monodentate chdo⁻ ligands are bound to the Pt coordination center at an sp³-carbon and at an enolate oxygen. Any other compounds such as the dialkyl have not been obtained from the solution. The water-soluble dialkylplatinum(II) compound [Pt(en)(dmbarb-C)₂]·2H₂O (II) via [Pt(en)(dmbarb-C)(dmbarb-O)] (I) was isolated, replacing Hchdo with 1,3-dimethylbarbituric acid (Hdmbarb) as another potential monodentate ligand.

As shown in Figs. 1 and 2, the Pt complexes of (I) and (II) are found to be linkage isomers; two crystallographically independent dmbarb⁻ anions coordinate to the Pt atom as monodentate ligands in common. In (I) one of the dmbarb⁻ anions is bound at C15 and the other at O24 of the deprotonated enol, similarly to chdo⁻ anions in (3). On the contrary in (II) both dmbarb⁻ anions coordinate to the Pt atom at C15 and C25 atoms. The C-bound β-diketonate or O-bound enolate forms of the dmba⁻ anions were confirmed by the bond lengths and angles. The angles about the donor C atoms are almost tetrahedral: 103.4 (3), 107.2 (3) and 117.1 (4)° for C15 in (I), 109.5 (3), 105.3 (3) and 115.9 (4) ° for C15 in (II) and 104.8 (3), 109.9 (3) and 116.8 (4) ° for C25 in (II). In (I) the enol O24—C24 bond length of 1.275 (5) Å are apparently longer than the carbonyl O22═C22 of 1.231 (5) and O26═C26 of 1.245 (5) Å. The Pt—C bond lengths, 2.112 (4) Å for (I), and 2.114 (4) and 2.117 (4) Å for (II), are comparable with that of (3), 2.123 (4) Å. Due to trans influence of the sp³-carbon atoms, the Pt—N bond lengths at trans to the Pt—C, 2.098 (3) Å for (I) and 2.087 (3) and 2.098 (3) Å for (II), are longer than that at trans to the Pt—O in (I), 2.015 (3) Å, as observed in (3) [2.070 (3) and 2.025 (3) Å]. The dmbarb⁻ ligands in both compounds are approximately planar within 0.04 Å, except for the sp³-carbon atoms, C15 in (I) and C15 and C25 in (II), with the respective deviations of 0.288 (6), 0.309 (6) and 0.242 (6) Å from the least-square planes. Ignoring the sp³-carbon atoms from the molecular planes of the dmbarb⁻ ligands, the C-bound are almost perpendicular to the Pt coordination planes with the dihedral angles of 88.8 (1)° for (I), and 85.5 (1) and 84.9 (1)° for (II); the angle for the O-bound in (I) is 59.5 (1)°. In (I) the two-dimensional hydrogen-bond network was formed along the bc plane by the amino N1 and N2 atoms of the en chelate and the carbonyl O16, O22 and O26 atoms of the dmbarb⁻ ligands (Table 2), while the closer three-dimensional framework was built up in (II) by the amino groups, the carbonyl groups and water molecules (Table 4).

The ¹H– and ¹³C-NMR spectra of (I) and (II) in D₂O solutions show that the molecular structures in the solutions are consistent with those in the solid state, and that (I) changes into (II) in two weeks at room temperature. No changes have been found in the spectrum of (II) afterward, at least for a month. Accordingly the dialkylplatinum(II) compound (II) should be a thermodynamically stable species in an aqueous solution, compared with the monoalkyl (I).

S2. Experimental

Each isomer was isolated by the following procedure: an aqueous solution of Hdmbarb (0.937 g, 6.001 mmol) was added to the yellow eluate containing [Pt(en)(OH)₂], prepared from [Pt(en)(ONO₂)₂] (1.135 g, 2.993 mmol). After rotoevaporation to 30 ml it was allowed to stand at 278 K for 2 d to form pale-yellow crystals of (I) (0.600 g, 35% yield). Analysis found: C 29.34, H 4.00, N 14.82%; calculated for C₁₄H₂₂N₆O₆Pt: C 29.74, H 3.92, N 14.86%. ¹H NMR (0.01 mol dm⁻³ in D₂O, 300 MHz): δ 5.66 (s, 1H, CH), 4.40 (s, 1H, CH), 3.08 (s, 3H, CH₃), 2.99 (s, 3H, CH₃), 2.92 (s, 6H, CH₃), 2.49 (m, 4H, CH₂) p.p.m.; ¹³C{¹H} NMR (75.5 MHz): δ 176.33 (C14, C16), 167.12 (C26), 165.73 (C24), 153.96, 153.23 (C12, C22), 80.07 (C25), 49.39, 45.49 (C1, C2), 47.20 (C15), 27.67, 27.63, 27.53, 26.34 (C11, C13, C21, C23). Another aqueous solution of [Pt(en)(OH)₂] prepared from [Pt(en)(ONO₂)₂] (0.379 g, 0.999 mmol) was rotoevaporated to 10 ml, and was added to 10 ml of an aqueous solution of Hdmbarb (0.312 g, 1.998 mmol). After standing at room temperature for 14 days, yellow crystals of (II) were obtained (0.336 g, 56% yield). Analysis found: C 27.84, H 4.34, N 14.04%; calculated for C₁₄H₂₆N₆O₈Pt: C 27.96, H 4.36, N 13.97%. ¹H NMR (0.01 mol dm⁻³ in D₂O, 300 MHz): δ 4.13 (s, 2H, CH), 3.07 (s, 12H, CH₃), 2.43 (s, 4H, CH₂), ¹³C{¹H} NMR (75.5 MHz): δ 176.80 (C14, C16, C24, C26), 154.17 (C12, C22), 47.21 (C1, C2, C15, C25), 27.69 (C11, C13, C21, C23).

Compound (I) is more soluble in H₂O than (II): up to 0.015 mol dm⁻³ for (I) and less than 0.01 mol dm⁻³ for (II) at room temperature. Both compounds were air-stable in the solid state, but (I) dissolved in H₂O has been changed into (II) in two weeks. It was difficult to recrystallize (I) from H₂O because of the contamination of (II), while (II) could be recrystallized from H₂O.

S3. Refinement

For both compounds H atoms other than those on H₂O were included as riding models and positions of the H atoms on H₂O in (II) were refined with O—H restrained at 0.82 (3) Å; U_iso(H) = 1.2U_eq(parent atom). The site-occupancy parameters of disordered ethylene chains in (II), were refined to 0.84 (1) for C1 and C2, and 0.16 (1) for C10 and C20.

Computing details

For both compounds, data collection: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1993a); cell refinement: MSC/AFC Diffractometer Control Software; data reduction: TEXSAN PROCESS (Molecular Structure Corporation, 1993b); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Burnett & Johnson, 1996); software used to prepare material for publication: SHELXL97.

Figures

	Fig. 1. The asymmetric unit of [Pt(en)(dmbarb-C)(dmbarb-O)], (I), showing displacement ellipsoids at the 50% probability level.
	Fig. 2. The asymmetric unit of [Pt(en)(dmbarb-C)2]·2H2O, (II). showing displacement ellipsoids at the 50% probability level. One disordered conformer of the en ligand is drawn with open circles and bonds.

(I)

Crystal data

[Pt(C2H8N2)(C6H7N2O3)2]	Z = 2
Mr = 565.47	F(000) = 548
Triclinic, P1	Dx = 2.036 Mg m^−3 Dm = 2.04 Mg m^−3 Dm measured by flotation in CCl4/CHBr3
a = 9.505 (2) Å	Mo Kα radiation, λ = 0.71069 Å
b = 11.2518 (9) Å	Cell parameters from 25 reflections
c = 9.464 (2) Å	θ = 16.9–17.5°
α = 103.10 (1)°	µ = 7.65 mm^−1
β = 110.52 (1)°	T = 296 K
γ = 87.93 (1)°	Thin plate, pale yellow
V = 922.2 (2) Å^3	0.20 × 0.10 × 0.07 mm

Data collection

Rigaku AFC7R diffractometer	4663 reflections with I > 2σ(I)
Radiation source: rotating Mo anticathode	Rint = 0.029
Graphite monochromator	θmax = 30.0°, θmin = 2.3°
ω/2θ scans	h = −13→0
Absorption correction: ψ scan (North et al., 1968)	k = −15→15
Tmin = 0.294, Tmax = 0.585	l = −12→13
5685 measured reflections	3 standard reflections every 150 reflections
5383 independent reflections	intensity decay: 0.9%

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.026	H-atom parameters constrained
wR(F^2) = 0.061	w = 1/[σ^2(Fo^2) + (0.0258P)^2 + 0.5877P] where P = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max = 0.001
5383 reflections	Δρmax = 1.17 e Å^−3
245 parameters	Δρmin = −1.14 e Å^−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 1997), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0023 (2)

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Pt	0.536793 (17)	0.341507 (13)	0.292565 (16)	0.02565 (5)
O12	1.0320 (5)	0.1670 (4)	0.4841 (5)	0.0697 (12)
O14	0.7685 (5)	0.3327 (4)	0.0803 (4)	0.0586 (10)
O16	0.8300 (4)	0.5307 (3)	0.5862 (4)	0.0485 (8)
O22	0.6747 (4)	−0.0157 (3)	0.7665 (4)	0.0509 (9)
O24	0.6351 (3)	0.2269 (3)	0.4347 (3)	0.0354 (6)
O26	0.4055 (4)	0.3242 (3)	0.8130 (3)	0.0399 (7)
N1	0.3161 (4)	0.2813 (3)	0.2493 (4)	0.0311 (7)
H1	0.3109	0.1997	0.2365	0.037*
H2	0.2876	0.3157	0.3300	0.037*
N2	0.4338 (4)	0.4354 (3)	0.1295 (4)	0.0329 (7)
H7	0.4761	0.5115	0.1589	0.039*
H8	0.4449	0.3984	0.0394	0.039*
N11	0.9318 (4)	0.3495 (4)	0.5363 (4)	0.0387 (8)
N13	0.8904 (5)	0.2415 (4)	0.2790 (5)	0.0447 (9)
N21	0.5280 (5)	0.1487 (3)	0.7792 (4)	0.0366 (8)
N23	0.6525 (4)	0.1078 (3)	0.6006 (4)	0.0318 (7)
C1	0.2156 (5)	0.3166 (4)	0.1069 (5)	0.0406 (10)
H3	0.1129	0.3194	0.1052	0.049*
H4	0.2180	0.2574	0.0157	0.049*
C2	0.2708 (5)	0.4413 (4)	0.1078 (5)	0.0383 (9)
H5	0.2152	0.4635	0.0106	0.046*
H6	0.2563	0.5023	0.1915	0.046*
C11	1.0067 (6)	0.3541 (6)	0.7020 (6)	0.0568 (14)
H111	1.0679	0.2848	0.7148	0.068*
H112	0.9323	0.3526	0.7490	0.068*
H113	1.0689	0.4279	0.7508	0.068*
C12	0.9547 (5)	0.2470 (4)	0.4346 (6)	0.0445 (11)
C13	0.9206 (7)	0.1357 (5)	0.1731 (8)	0.0677 (17)
H131	0.8697	0.1424	0.0681	0.081*
H132	0.8850	0.0624	0.1880	0.081*
H133	1.0269	0.1329	0.1938	0.081*
C14	0.8011 (5)	0.3322 (4)	0.2170 (5)	0.0390 (10)
C15	0.7476 (5)	0.4199 (4)	0.3248 (5)	0.0319 (8)
H15	0.7334	0.4984	0.2943	0.038*
C16	0.8374 (5)	0.4397 (4)	0.4896 (5)	0.0342 (8)
C21	0.4850 (7)	0.1102 (5)	0.8964 (6)	0.0554 (14)
H211	0.4200	0.1684	0.9295	0.067*
H212	0.5735	0.1055	0.9836	0.067*
H213	0.4332	0.0315	0.8532	0.067*
C22	0.6214 (5)	0.0747 (4)	0.7180 (5)	0.0354 (9)
C23	0.7497 (6)	0.0287 (4)	0.5340 (6)	0.0473 (11)
H231	0.7637	0.0603	0.4535	0.057*
H232	0.7038	−0.0523	0.4914	0.057*
H233	0.8455	0.0262	0.6133	0.057*
C24	0.5974 (4)	0.2120 (4)	0.5465 (4)	0.0288 (7)
C25	0.5121 (5)	0.2863 (3)	0.6163 (4)	0.0302 (8)
H25	0.4764	0.3567	0.5823	0.036*
C26	0.4767 (5)	0.2590 (4)	0.7389 (4)	0.0311 (8)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Pt	0.03179 (8)	0.02414 (8)	0.02707 (8)	0.00483 (5)	0.01500 (5)	0.01076 (5)
O12	0.056 (2)	0.060 (3)	0.095 (3)	0.030 (2)	0.026 (2)	0.028 (2)
O14	0.078 (3)	0.068 (3)	0.0430 (19)	−0.001 (2)	0.0351 (19)	0.0153 (18)
O16	0.054 (2)	0.0437 (19)	0.0465 (19)	0.0031 (15)	0.0232 (16)	−0.0005 (15)
O22	0.077 (3)	0.0315 (16)	0.0486 (19)	0.0145 (16)	0.0204 (18)	0.0221 (14)
O24	0.0383 (16)	0.0381 (16)	0.0429 (16)	0.0141 (12)	0.0219 (13)	0.0247 (13)
O26	0.055 (2)	0.0375 (16)	0.0335 (15)	0.0099 (14)	0.0231 (14)	0.0100 (12)
N1	0.0337 (17)	0.0283 (16)	0.0360 (17)	0.0040 (13)	0.0151 (14)	0.0121 (13)
N2	0.049 (2)	0.0282 (16)	0.0264 (15)	0.0034 (14)	0.0176 (15)	0.0089 (13)
N11	0.0318 (18)	0.045 (2)	0.042 (2)	0.0052 (15)	0.0144 (16)	0.0128 (16)
N13	0.043 (2)	0.041 (2)	0.057 (2)	0.0065 (17)	0.031 (2)	0.0034 (18)
N21	0.058 (2)	0.0277 (17)	0.0317 (17)	0.0061 (16)	0.0211 (17)	0.0146 (14)
N23	0.0377 (18)	0.0248 (16)	0.0370 (18)	0.0072 (13)	0.0150 (15)	0.0132 (13)
C1	0.040 (2)	0.043 (2)	0.036 (2)	−0.0017 (19)	0.0075 (18)	0.0115 (18)
C2	0.040 (2)	0.041 (2)	0.036 (2)	0.0097 (18)	0.0103 (18)	0.0181 (18)
C11	0.042 (3)	0.073 (4)	0.051 (3)	0.002 (3)	0.007 (2)	0.023 (3)
C12	0.029 (2)	0.043 (3)	0.067 (3)	0.0089 (18)	0.022 (2)	0.017 (2)
C13	0.067 (4)	0.048 (3)	0.090 (5)	0.011 (3)	0.045 (3)	−0.006 (3)
C14	0.038 (2)	0.042 (2)	0.043 (2)	−0.0058 (18)	0.0232 (19)	0.0055 (19)
C15	0.036 (2)	0.0283 (19)	0.040 (2)	0.0043 (15)	0.0200 (17)	0.0152 (16)
C16	0.031 (2)	0.035 (2)	0.042 (2)	0.0008 (16)	0.0189 (18)	0.0089 (17)
C21	0.099 (5)	0.041 (3)	0.044 (3)	0.007 (3)	0.042 (3)	0.019 (2)
C22	0.050 (3)	0.0231 (18)	0.0317 (19)	−0.0013 (17)	0.0096 (18)	0.0097 (15)
C23	0.051 (3)	0.041 (3)	0.057 (3)	0.018 (2)	0.024 (2)	0.019 (2)
C24	0.0286 (18)	0.0287 (18)	0.0302 (18)	0.0021 (14)	0.0080 (15)	0.0128 (15)
C25	0.039 (2)	0.0236 (17)	0.0315 (19)	0.0073 (15)	0.0142 (16)	0.0118 (15)
C26	0.036 (2)	0.0277 (19)	0.0292 (18)	0.0008 (15)	0.0103 (16)	0.0086 (15)

Geometric parameters (Å, º)

Pt—N1	2.098 (3)	O22—C22	1.231 (5)
Pt—N2	2.015 (3)	O24—C24	1.275 (5)
Pt—C15	2.112 (4)	O26—C26	1.245 (5)
Pt—O24	2.041 (3)	N1—H1	0.90
N1—C1	1.483 (5)	N1—H2	0.90
N2—C2	1.491 (6)	N2—H7	0.90
C1—C2	1.513 (6)	N2—H8	0.90
N11—C11	1.467 (6)	C1—H3	0.97
N11—C12	1.389 (6)	C1—H4	0.97
N11—C16	1.376 (6)	C2—H5	0.97
N13—C12	1.370 (7)	C2—H6	0.97
N13—C13	1.463 (6)	C11—H111	0.96
N13—C14	1.402 (6)	C11—H112	0.96
C14—C15	1.464 (6)	C11—H113	0.96
C15—C16	1.460 (6)	C13—H131	0.96
O12—C12	1.212 (6)	C13—H132	0.96
O14—C14	1.222 (5)	C13—H133	0.96
O16—C16	1.227 (5)	C15—H15	0.98
N21—C22	1.380 (6)	C21—H211	0.96
N21—C26	1.401 (5)	C21—H212	0.96
N21—C21	1.461 (5)	C21—H213	0.96
N23—C22	1.374 (5)	C23—H231	0.96
N23—C24	1.397 (5)	C23—H232	0.96
N23—C23	1.463 (5)	C23—H233	0.96
C24—C25	1.368 (5)	C25—H25	0.93
C25—C26	1.413 (5)
N1—Pt—N2	83.2 (1)	C1—N1—H2	110.0
N1—Pt—C15	173.2 (1)	Pt—N1—H2	110.0
N1—Pt—O24	94.8 (1)	H1—N1—H2	108.4
N2—Pt—C15	90.4 (1)	C2—N2—H7	109.8
N2—Pt—O24	172.6 (1)	Pt—N2—H7	109.8
C15—Pt—O24	91.9 (1)	C2—N2—H8	109.8
Pt—C15—C14	103.4 (3)	Pt—N2—H8	109.8
Pt—C15—C16	107.2 (3)	H7—N2—H8	108.2
Pt—O24—C24	125.1 (3)	N1—C1—H3	110.2
Pt—N1—C1	108.4 (3)	C2—C1—H3	110.2
Pt—N2—C2	109.5 (2)	N1—C1—H4	110.2
N1—C1—C2	107.7 (3)	C2—C1—H4	110.2
N2—C2—C1	107.9 (3)	H3—C1—H4	108.5
C12—N13—C14	123.7 (4)	N2—C2—H5	110.1
C12—N13—C13	117.4 (5)	C1—C2—H5	110.1
C14—N13—C13	118.9 (5)	N2—C2—H6	110.1
C16—N11—C12	123.6 (4)	C1—C2—H6	110.1
C16—N11—C11	119.9 (4)	H5—C2—H6	108.4
C12—N11—C11	116.3 (4)	N13—C13—H131	109.5
O12—C12—N13	121.9 (5)	N13—C13—H132	109.5
O12—C12—N11	120.2 (5)	H131—C13—H132	109.5
N13—C12—N11	117.8 (4)	N13—C13—H133	109.5
O16—C16—N11	119.5 (4)	H131—C13—H133	109.5
N11—C16—C15	117.2 (4)	H132—C13—H133	109.5
O14—C14—N13	120.4 (4)	N11—C11—H111	109.5
N13—C14—C15	115.6 (4)	N11—C11—H112	109.5
O14—C14—C15	124.0 (5)	H111—C11—H112	109.5
C14—C15—C16	117.1 (4)	N11—C11—H113	109.5
O16—C16—C15	123.2 (4)	H111—C11—H113	109.5
C22—N21—C26	124.0 (3)	H112—C11—H113	109.5
C22—N21—C21	117.2 (4)	C16—C15—H15	109.6
C26—N21—C21	118.8 (4)	C14—C15—H15	109.6
C22—N23—C24	123.0 (3)	Pt—C15—H15	109.6
C22—N23—C23	116.6 (3)	N21—C21—H211	109.5
C24—N23—C23	120.4 (3)	N21—C21—H212	109.5
O22—C22—N23	121.7 (4)	H211—C21—H212	109.5
O22—C22—N21	121.9 (4)	N21—C21—H213	109.5
N23—C22—N21	116.4 (3)	H211—C21—H213	109.5
O24—C24—N23	114.3 (3)	H212—C21—H213	109.5
C25—C24—N23	118.6 (3)	N23—C23—H231	109.5
O26—C26—N21	118.3 (4)	N23—C23—H232	109.5
N21—C26—C25	116.0 (4)	H231—C23—H232	109.5
O24—C24—C25	127.1 (4)	N23—C23—H233	109.5
C24—C25—C26	121.7 (4)	H231—C23—H233	109.5
O26—C26—C25	125.8 (4)	H232—C23—H233	109.5
C1—N1—H1	110.0	C24—C25—H25	119.1
Pt—N1—H1	110.0	C26—C25—H25	119.1
N2—Pt—O24—C24	−121.8 (9)	O24—Pt—C15—C14	81.3 (3)
N1—Pt—O24—C24	−48.1 (3)	N1—Pt—C15—C14	−112.8 (12)
C15—Pt—O24—C24	130.2 (3)	C12—N13—C14—O14	167.4 (4)
N2—Pt—N1—C1	12.0 (3)	C13—N13—C14—O14	−11.1 (7)
O24—Pt—N1—C1	−160.9 (3)	C12—N13—C14—C15	−14.8 (6)
C15—Pt—N1—C1	33.3 (13)	C13—N13—C14—C15	166.6 (4)
O24—Pt—N2—C2	91.3 (10)	C16—C15—C14—O14	−156.6 (4)
N1—Pt—N2—C2	16.9 (3)	Pt—C15—C14—O14	85.7 (5)
C15—Pt—N2—C2	−160.6 (3)	C16—C15—C14—N13	25.7 (5)
Pt—N1—C1—C2	−37.9 (4)	Pt—C15—C14—N13	−91.9 (4)
Pt—N2—C2—C1	−42.5 (4)	C24—N23—C22—O22	−178.0 (4)
N1—C1—C2—N2	53.1 (4)	C23—N23—C22—O22	1.2 (6)
C14—N13—C12—O12	−179.7 (5)	C24—N23—C22—N21	1.6 (6)
C13—N13—C12—O12	−1.1 (7)	C23—N23—C22—N21	−179.2 (4)
C14—N13—C12—N11	−1.1 (7)	C26—N21—C22—O22	173.3 (4)
C13—N13—C12—N11	177.4 (4)	C21—N21—C22—O22	−4.6 (7)
C16—N11—C12—O12	−175.2 (4)	C26—N21—C22—N23	−6.3 (6)
C11—N11—C12—O12	0.6 (7)	C21—N21—C22—N23	175.8 (4)
C16—N11—C12—N13	6.3 (6)	Pt—O24—C24—C25	−16.4 (6)
C11—N11—C12—N13	−178.0 (4)	Pt—O24—C24—N23	164.2 (3)
C12—N11—C16—O16	−175.9 (4)	C22—N23—C24—O24	−178.6 (4)
C11—N11—C16—O16	8.5 (6)	C23—N23—C24—O24	2.2 (6)
C12—N11—C16—C15	5.4 (6)	C22—N23—C24—C25	1.9 (6)
C11—N11—C16—C15	−170.2 (4)	C23—N23—C24—C25	−177.2 (4)
O16—C16—C15—C14	159.9 (4)	O24—C24—C25—C26	179.4 (4)
N11—C16—C15—C14	−21.5 (5)	N23—C24—C25—C26	−1.2 (6)
O16—C16—C15—Pt	−84.6 (4)	C22—N21—C26—O26	−172.8 (4)
N11—C16—C15—Pt	94.1 (4)	C21—N21—C26—O26	5.1 (6)
N2—Pt—C15—C16	144.0 (3)	C22—N21—C26—C25	6.9 (6)
O24—Pt—C15—C16	−43.0 (3)	C21—N21—C26—C25	−175.1 (4)
N1—Pt—C15—C16	122.8 (11)	C24—C25—C26—O26	176.7 (4)
N2—Pt—C15—C14	−91.7 (3)	C24—C25—C26—N21	−3.0 (6)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O22^i	0.90	2.06	2.958 (5)	172
N1—H2···O16^ii	0.90	2.17	2.939 (5)	142
N2—H7···O26^ii	0.90	2.11	2.998 (5)	167
N2—H8···O26^iii	0.90	2.02	2.893 (4)	163

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

(II)

Crystal data

[Pt(C2H8N2)(C6H7N2O3)2]·2H2O	F(000) = 1176
Mr = 601.50	Dx = 2.049 Mg m^−3 Dm = 2.04 Mg m^−3 Dm measured by flotation in CCl4/CHBr3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71069 Å
a = 12.840 (2) Å	Cell parameters from 25 reflections
b = 10.7834 (9) Å	θ = 19.1–19.9°
c = 14.727 (2) Å	µ = 7.25 mm^−1
β = 107.051 (9)°	T = 296 K
V = 1949.5 (4) Å^3	Prism, yellow
Z = 4	0.16 × 0.16 × 0.07 mm

Data collection

Rigaku AFC7R diffractometer	4415 reflections with I > 2σ(I)
Radiation source: rotating Mo anticathode	Rint = 0.026
Graphite monochromator	θmax = 30.0°, θmin = 2.4°
ω/2θ scans	h = 0→18
Absorption correction: ψ scan (North et al., 1968)	k = −15→0
Tmin = 0.390, Tmax = 0.631	l = −20→19
5892 measured reflections	3 standard reflections every 150 reflections
5664 independent reflections	intensity decay: 0.9%

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.027	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.065	w = 1/[σ^2(Fo^2) + (0.0275P)^2 + 0.6P] where P = (Fo^2 + 2Fc^2)/3
S = 1.02	(Δ/σ)max = 0.003
5664 reflections	Δρmax = 0.88 e Å^−3
284 parameters	Δρmin = −0.94 e Å^−3
4 restraints	Extinction correction: SHELXL97 (Sheldrick, 1997), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.00092 (9)

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
Pt	0.729256 (11)	0.195623 (13)	0.579509 (9)	0.02254 (5)
O12	1.0368 (3)	0.1008 (3)	0.4434 (3)	0.0523 (9)
O14	0.9398 (3)	0.4185 (4)	0.6000 (3)	0.0533 (9)
O16	0.6889 (3)	0.2418 (4)	0.3382 (2)	0.0459 (8)
O22	0.3835 (3)	0.2825 (4)	0.6845 (3)	0.0525 (10)
O24	0.6224 (3)	0.4887 (3)	0.5682 (2)	0.0398 (7)
O26	0.4661 (3)	0.1183 (3)	0.4317 (2)	0.0418 (8)
O1	1.0471 (4)	0.3422 (4)	0.3168 (4)	0.0695 (13)
H11	1.108 (3)	0.310 (6)	0.327 (5)	0.083*
H12	1.063 (6)	0.412 (4)	0.340 (5)	0.083*
O2	0.2689 (4)	0.1927 (4)	0.8260 (4)	0.0746 (14)
H21	0.305 (6)	0.240 (6)	0.804 (5)	0.089*
H22	0.307 (5)	0.134 (5)	0.855 (4)	0.089*
N1	0.6697 (3)	0.0893 (3)	0.6718 (2)	0.0293 (7)
H1	0.6359	0.1388	0.7035	0.035*
H2	0.6208	0.0341	0.6383	0.035*
N2	0.8719 (3)	0.0964 (3)	0.6454 (2)	0.0318 (7)
H7	0.9053	0.0743	0.6020	0.038*
H8	0.9179	0.1442	0.6894	0.038*
N11	0.8601 (3)	0.1640 (3)	0.3930 (3)	0.0360 (9)
N13	0.9870 (3)	0.2583 (4)	0.5237 (3)	0.0367 (8)
N21	0.4327 (3)	0.1915 (3)	0.5646 (3)	0.0319 (7)
N23	0.5151 (3)	0.3778 (3)	0.6361 (2)	0.0314 (8)
C1	0.7621 (5)	0.0219 (6)	0.7413 (5)	0.0343 (13)	0.840 (12)
H3	0.7969	0.0760	0.7941	0.041*	0.840 (12)
H4	0.7344	−0.0503	0.7661	0.041*	0.840 (12)
C2	0.8427 (4)	−0.0173 (5)	0.6915 (4)	0.0335 (14)	0.840 (12)
H5	0.8111	−0.0797	0.6440	0.040*	0.840 (12)
H6	0.9071	−0.0519	0.7365	0.040*	0.840 (12)
C10	0.747 (3)	−0.011 (3)	0.708 (2)	0.028 (7)*	0.160 (12)
H30	0.7432	−0.0728	0.6596	0.033*	0.160 (12)
H40	0.7325	−0.0507	0.7623	0.033*	0.160 (12)
C20	0.859 (2)	0.050 (2)	0.7380 (17)	0.025 (6)*	0.160 (12)
H50	0.8613	0.1179	0.7817	0.030*	0.160 (12)
H60	0.9154	−0.0095	0.7676	0.030*	0.160 (12)
C11	0.8411 (5)	0.0824 (6)	0.3094 (4)	0.0589 (15)
H111	0.8963	0.0194	0.3216	0.071*
H112	0.8437	0.1305	0.2553	0.071*
H113	0.7708	0.0441	0.2969	0.071*
C12	0.9655 (4)	0.1692 (4)	0.4527 (3)	0.0350 (10)
C13	1.1026 (4)	0.2786 (6)	0.5757 (4)	0.0636 (18)
H131	1.1458	0.2710	0.5326	0.076*
H132	1.1258	0.2179	0.6252	0.076*
H133	1.1116	0.3602	0.6030	0.076*
C14	0.9096 (4)	0.3347 (4)	0.5420 (3)	0.0322 (9)
C15	0.7955 (3)	0.3076 (4)	0.4924 (3)	0.0277 (8)
H15	0.7551	0.3859	0.4800	0.033*
C16	0.7753 (4)	0.2393 (4)	0.4025 (3)	0.0322 (9)
C21	0.3463 (4)	0.0982 (5)	0.5553 (4)	0.0440 (11)
H211	0.3435	0.0447	0.5026	0.053*
H212	0.2774	0.1393	0.5449	0.053*
H213	0.3617	0.0499	0.6125	0.053*
C22	0.4406 (4)	0.2843 (4)	0.6320 (3)	0.0352 (10)
C23	0.5185 (4)	0.4761 (5)	0.7054 (4)	0.0481 (13)
H231	0.5672	0.5404	0.6982	0.058*
H232	0.5437	0.4424	0.7684	0.058*
H233	0.4468	0.5099	0.6950	0.058*
C24	0.5752 (3)	0.3907 (4)	0.5714 (3)	0.0283 (8)
C25	0.5786 (3)	0.2826 (4)	0.5119 (3)	0.0271 (8)
H25	0.5805	0.3122	0.4495	0.032*
C26	0.4900 (3)	0.1931 (4)	0.4978 (3)	0.0285 (8)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Pt	0.02121 (8)	0.02483 (8)	0.02221 (7)	0.00130 (6)	0.00738 (5)	−0.00083 (6)
O12	0.052 (2)	0.044 (2)	0.070 (2)	0.0140 (18)	0.0320 (19)	0.0010 (18)
O14	0.045 (2)	0.056 (2)	0.061 (2)	−0.0119 (18)	0.0181 (17)	−0.0272 (19)
O16	0.0354 (18)	0.069 (2)	0.0298 (16)	−0.0067 (17)	0.0049 (14)	0.0065 (16)
O22	0.053 (2)	0.062 (3)	0.056 (2)	−0.0054 (19)	0.0377 (19)	−0.0109 (18)
O24	0.0382 (18)	0.0294 (16)	0.0532 (19)	−0.0027 (14)	0.0157 (15)	−0.0042 (14)
O26	0.0394 (19)	0.049 (2)	0.0376 (17)	−0.0076 (15)	0.0116 (14)	−0.0142 (15)
O1	0.067 (3)	0.051 (3)	0.077 (3)	0.000 (2)	0.000 (3)	−0.004 (2)
O2	0.064 (3)	0.046 (3)	0.116 (4)	0.013 (2)	0.029 (3)	0.023 (3)
N1	0.0240 (16)	0.0343 (19)	0.0300 (16)	−0.0009 (15)	0.0085 (13)	0.0024 (15)
N2	0.0255 (17)	0.035 (2)	0.0362 (18)	0.0052 (15)	0.0116 (14)	0.0057 (16)
N11	0.043 (2)	0.036 (2)	0.0340 (19)	−0.0038 (17)	0.0193 (17)	−0.0070 (15)
N13	0.0283 (19)	0.045 (2)	0.037 (2)	0.0011 (17)	0.0095 (15)	−0.0037 (17)
N21	0.0277 (18)	0.0333 (19)	0.0360 (18)	−0.0020 (15)	0.0114 (14)	−0.0048 (16)
N23	0.0297 (18)	0.0338 (19)	0.0315 (18)	0.0051 (15)	0.0105 (14)	−0.0043 (15)
C1	0.036 (3)	0.036 (3)	0.030 (3)	0.003 (2)	0.008 (2)	0.007 (3)
C2	0.035 (3)	0.031 (3)	0.035 (3)	0.006 (2)	0.011 (2)	0.007 (2)
C11	0.067 (4)	0.061 (4)	0.055 (3)	−0.010 (3)	0.027 (3)	−0.025 (3)
C12	0.037 (2)	0.035 (2)	0.039 (2)	0.0028 (18)	0.021 (2)	0.0049 (18)
C13	0.031 (3)	0.094 (5)	0.062 (4)	−0.001 (3)	0.009 (2)	−0.025 (3)
C14	0.032 (2)	0.031 (2)	0.037 (2)	−0.0012 (17)	0.0154 (18)	−0.0056 (17)
C15	0.027 (2)	0.029 (2)	0.0291 (19)	−0.0002 (17)	0.0120 (15)	0.0025 (16)
C16	0.032 (2)	0.037 (2)	0.031 (2)	−0.0034 (18)	0.0136 (18)	0.0047 (17)
C21	0.029 (2)	0.054 (3)	0.052 (3)	−0.007 (2)	0.017 (2)	−0.004 (2)
C22	0.029 (2)	0.040 (3)	0.036 (2)	0.0041 (18)	0.0096 (18)	−0.0018 (19)
C23	0.057 (3)	0.044 (3)	0.048 (3)	0.000 (2)	0.023 (2)	−0.017 (2)
C24	0.0227 (19)	0.031 (2)	0.031 (2)	0.0052 (16)	0.0073 (15)	−0.0002 (16)
C25	0.0231 (19)	0.033 (2)	0.0256 (18)	0.0065 (16)	0.0081 (15)	0.0023 (15)
C26	0.0201 (18)	0.036 (2)	0.0272 (17)	0.0033 (17)	0.0035 (14)	0.0010 (17)

Geometric parameters (Å, º)

Pt—N1	2.087 (3)	O26—C26	1.232 (5)
Pt—N2	2.098 (3)	O1—H11	0.83 (3)
Pt—C15	2.114 (4)	O1—H12	0.83 (3)
Pt—C25	2.117 (4)	O2—H21	0.82 (3)
C1—C2	1.495 (8)	O2—H22	0.84 (3)
C10—C20	1.52 (4)	N1—H1	0.90
N1—C10	1.46 (3)	N1—H2	0.90
N1—C1	1.507 (6)	N2—H7	0.90
N2—C2	1.501 (6)	N2—H8	0.90
N2—C20	1.51 (2)	C1—H3	0.97
N11—C11	1.475 (6)	C1—H4	0.97
N11—C12	1.382 (6)	C2—H5	0.97
N11—C16	1.397 (6)	C2—H6	0.97
N13—C12	1.387 (6)	C10—H30	0.97
N13—C13	1.474 (6)	C10—H40	0.97
N13—C14	1.377 (6)	C20—H50	0.97
C14—C15	1.462 (6)	C20—H60	0.97
C15—C16	1.470 (6)	C11—H111	0.96
O12—C12	1.214 (5)	C11—H112	0.96
O14—C14	1.225 (5)	C11—H113	0.96
O16—C16	1.230 (5)	C13—H131	0.96
N21—C21	1.474 (6)	C13—H132	0.96
N21—C22	1.393 (6)	C13—H133	0.96
N21—C26	1.390 (5)	C15—H15	0.98
N23—C22	1.379 (6)	C21—H211	0.96
N23—C23	1.463 (5)	C21—H212	0.96
N23—C24	1.396 (5)	C21—H213	0.96
C24—C25	1.467 (6)	C23—H231	0.96
C25—C26	1.460 (6)	C23—H232	0.96
O22—C22	1.212 (5)	C23—H233	0.96
O24—C24	1.226 (5)	C25—H25	0.98
N1—Pt—N2	81.7 (1)	H1—N1—H2	108.2
N1—Pt—C15	177.0 (1)	C2—N2—H7	109.9
N1—Pt—C25	95.2 (1)	C20—N2—H7	139.2
N2—Pt—C15	96.9 (1)	Pt—N2—H7	109.9
N2—Pt—C25	175.6 (1)	C2—N2—H8	109.9
C15—Pt—C25	86.4 (2)	C20—N2—H8	76.2
Pt—C15—C14	109.5 (3)	Pt—N2—H8	109.9
Pt—C15—C16	105.3 (3)	H7—N2—H8	108.3
Pt—C25—C24	104.8 (3)	C2—C1—H3	109.9
Pt—C25—C26	109.9 (3)	N1—C1—H3	109.9
Pt—N1—C1	110.0 (3)	C2—C1—H4	109.9
Pt—N2—C2	109.0 (3)	N1—C1—H4	109.9
N1—C1—C2	108.8 (4)	H3—C1—H4	108.3
N2—C2—C1	107.0 (4)	C1—C2—H5	110.3
Pt—N1—C10	107.8 (12)	N2—C2—H5	110.3
Pt—N2—C20	105.9 (10)	C1—C2—H6	110.3
N1—C10—C20	106 (2)	N2—C2—H6	110.3
N2—C20—C10	103 (2)	H5—C2—H6	108.6
C12—N11—C16	124.0 (4)	N1—C10—H30	110.6
C12—N11—C11	116.5 (4)	C20—C10—H30	110.6
C16—N11—C11	119.2 (4)	N1—C10—H40	110.6
C14—N13—C12	124.6 (4)	C20—C10—H40	110.6
C14—N13—C13	118.9 (4)	H30—C10—H40	108.7
C12—N13—C13	116.2 (4)	N2—C20—H50	111.1
O12—C12—N11	122.3 (4)	C10—C20—H50	111.1
O12—C12—N13	121.0 (5)	N2—C20—H60	111.1
N11—C12—N13	116.6 (4)	C10—C20—H60	111.1
O16—C16—N11	119.3 (4)	H50—C20—H60	109.1
N11—C16—C15	116.4 (4)	N13—C13—H131	109.5
N13—C14—C15	117.2 (4)	N13—C13—H132	109.5
O14—C14—N13	118.6 (4)	H131—C13—H132	109.5
O14—C14—C15	124.1 (4)	N13—C13—H133	109.5
C14—C15—C16	115.9 (4)	H131—C13—H133	109.5
O16—C16—C15	124.3 (4)	H132—C13—H133	109.5
C26—N21—C22	123.5 (4)	N11—C11—H111	109.5
C26—N21—C21	118.9 (4)	N11—C11—H112	109.5
C22—N21—C21	116.9 (4)	H111—C11—H112	109.5
C22—N23—C24	123.9 (4)	N11—C11—H113	109.5
C22—N23—C23	115.9 (4)	H111—C11—H113	109.5
C24—N23—C23	119.6 (4)	H112—C11—H113	109.5
O22—C22—N23	121.8 (4)	C14—C15—H15	108.6
O22—C22—N21	120.8 (4)	C16—C15—H15	108.6
N23—C22—N21	117.4 (4)	Pt—C15—H15	108.6
O24—C24—N23	119.4 (4)	N21—C21—H211	109.5
N23—C24—C25	116.6 (4)	N21—C21—H212	109.5
O26—C26—N21	119.3 (4)	H211—C21—H212	109.5
N21—C26—C25	117.4 (4)	N21—C21—H213	109.5
O24—C24—C25	124.0 (4)	H211—C21—H213	109.5
C24—C25—C26	116.8 (4)	H212—C21—H213	109.5
O26—C26—C25	123.3 (4)	N23—C23—H231	109.5
C22—O22—H21	165 (2)	N23—C23—H232	109.5
H11—O1—H12	101 (7)	H231—C23—H232	109.5
H21—O2—H22	111 (7)	N23—C23—H233	109.5
C10—N1—H1	128.9	H231—C23—H233	109.5
C1—N1—H1	109.7	H232—C23—H233	109.5
Pt—N1—H1	109.7	C26—C25—H25	108.4
C10—N1—H2	90.2	C24—C25—H25	108.4
C1—N1—H2	109.7	Pt—C25—H25	108.4
Pt—N1—H2	109.7
N2—Pt—N1—C10	−14.5 (14)	C25—Pt—C15—C16	−85.2 (3)
C15—Pt—N1—C10	−77 (3)	C12—N13—C14—O14	−172.5 (4)
C25—Pt—N1—C10	162.3 (14)	C13—N13—C14—O14	1.1 (7)
N2—Pt—N1—C1	9.4 (4)	C12—N13—C14—C15	9.3 (7)
C15—Pt—N1—C1	−53 (3)	C13—N13—C14—C15	−177.1 (4)
C25—Pt—N1—C1	−173.8 (4)	C16—C15—C14—O14	157.5 (5)
N1—Pt—N2—C2	19.1 (3)	Pt—C15—C14—O14	−83.6 (5)
C15—Pt—N2—C2	−163.6 (3)	C16—C15—C14—N13	−24.4 (6)
C25—Pt—N2—C2	−27.2 (19)	Pt—C15—C14—N13	94.6 (4)
N1—Pt—N2—C20	−20.6 (11)	H21—O22—C22—N23	−105 (7)
C15—Pt—N2—C20	156.7 (11)	O2—O22—C22—N23	−129.7 (10)
C25—Pt—N2—C20	−67 (2)	H21—O22—C22—N21	75 (7)
C10—N1—C1—C2	52 (3)	O2—O22—C22—N21	50.6 (13)
Pt—N1—C1—C2	−36.6 (6)	C24—N23—C22—O22	−173.6 (4)
N1—C1—C2—N2	53.0 (6)	C23—N23—C22—O22	−1.8 (7)
C20—N2—C2—C1	47.6 (16)	C24—N23—C22—N21	6.1 (6)
Pt—N2—C2—C1	−44.1 (5)	C23—N23—C22—N21	177.9 (4)
C1—N1—C10—C20	−53 (3)	C26—N21—C22—O22	175.1 (4)
Pt—N1—C10—C20	47 (2)	C21—N21—C22—O22	4.9 (7)
C2—N2—C20—C10	−50.2 (17)	C26—N21—C22—N23	−4.6 (6)
Pt—N2—C20—C10	50 (2)	C21—N21—C22—N23	−174.8 (4)
N1—C10—C20—N2	−65 (2)	C22—N23—C24—O24	165.2 (4)
C16—N11—C12—O12	178.6 (4)	C23—N23—C24—O24	−6.3 (6)
C11—N11—C12—O12	−7.8 (7)	C22—N23—C24—C25	−15.7 (6)
C16—N11—C12—N13	−2.3 (6)	C23—N23—C24—C25	172.8 (4)
C11—N11—C12—N13	171.3 (4)	O24—C24—C25—C26	−157.9 (4)
C14—N13—C12—O12	−176.4 (4)	N23—C24—C25—C26	23.1 (5)
C13—N13—C12—O12	9.9 (7)	O24—C24—C25—Pt	80.2 (4)
C14—N13—C12—N11	4.5 (7)	N23—C24—C25—Pt	−98.8 (3)
C13—N13—C12—N11	−169.3 (5)	N1—Pt—C25—C26	−39.7 (3)
C12—N11—C16—O16	168.9 (4)	N2—Pt—C25—C26	6.2 (19)
C11—N11—C16—O16	−4.5 (7)	C15—Pt—C25—C26	142.9 (3)
C12—N11—C16—C15	−13.4 (6)	N1—Pt—C25—C24	86.6 (3)
C11—N11—C16—C15	173.2 (4)	N2—Pt—C25—C24	132.5 (17)
O16—C16—C15—C14	−156.2 (4)	C15—Pt—C25—C24	−90.8 (3)
N11—C16—C15—C14	26.2 (6)	C22—N21—C26—O26	−168.8 (4)
O16—C16—C15—Pt	82.6 (5)	C21—N21—C26—O26	1.3 (6)
N11—C16—C15—Pt	−95.0 (4)	C22—N21—C26—C25	12.9 (6)
N1—Pt—C15—C14	28 (3)	C21—N21—C26—C25	−177.0 (4)
N2—Pt—C15—C14	−33.5 (3)	C24—C25—C26—O26	160.0 (4)
C25—Pt—C15—C14	149.5 (3)	Pt—C25—C26—O26	−80.9 (4)
N1—Pt—C15—C16	154 (3)	C24—C25—C26—N21	−21.9 (5)
N2—Pt—C15—C16	91.7 (3)	Pt—C25—C26—N21	97.2 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O16^i	0.90	2.29	3.005 (5)	136
N1—H2···O26^ii	0.90	2.08	2.969 (5)	169
N2—H7···O12^iii	0.90	2.20	2.915 (5)	136
N2—H8···O1^i	0.90	2.11	2.923 (6)	149
O1—H11···O2^iv	0.83 (3)	2.06 (4)	2.837 (7)	154 (7)
O1—H12···O14^v	0.83 (3)	2.03 (3)	2.840 (6)	165 (7)
O2—H21···O22	0.82 (3)	2.31 (5)	3.040 (6)	149 (7)
O2—H22···O24^vi	0.84 (3)	1.99 (3)	2.819 (5)	171 (7)

Symmetry codes: (i) x, −y+1/2, z+1/2; (ii) −x+1, −y, −z+1; (iii) −x+2, −y, −z+1; (iv) x+1, −y+1/2, z−1/2; (v) −x+2, −y+1, −z+1; (vi) −x+1, y−1/2, −z+3/2.