Crystal structure of [K(18-crown-6)]+ 2[Pt(CN)4]2.

In the title compound, di-μ-cyanato-1:2κ2 N:C;2:3κ2 C:N-di-cyanato-2κ2 C-bis-(1,4,7,10,13,16-hexa-oxa-cyclo-octa-deca-ne)-1κ6 O;3κ6 O-1,3-dipotassium(I)-2-platinum(II), [K2Pt(CN)4(C12H24O6)2] or [K(18-crown-6)]2·[Pt(CN)4], two trans-orientated cyano groups of the square-planar [Pt(CN)4]2- dianion (Pt site symmetry ) bind to one potassium ion each, which are additionally coordinated by the six O atoms of 18-crown-6. No Pt⋯Pt inter-actions occur in the crystal, but very weak Pt⋯H contacts (2.79 Å) are observed. © Sellin and Malischewski 2019.

Chemical context

Polycyano­metallates are an important class of inorganic compounds with intriguing properties. As a result of their anionic nature and high nucleophilicity, they have been widely used as metallo-ligands in coordination chemistry. Depending on the geometry of the polycyano­metallate, various topologies can be realized (Alexandrov et al., 2015 ▸). While photomagnetic effects have been predominantly realized with hexa- and octa­cyano­metallates (Ohkoshi et al., 2012 ▸), studies on tetra­cyano­platinates and their derivatives have focused on the high electrical conductivities of mixed-valent Krogmann’s salts K2[Pt(CN)4]Br0.32·2.6H2O (Krogmann, 1969 ▸), vapochromic sensor materials (e.g. Zn[Pt(CN)4] for ammonia (Varju et al., 2019 ▸) and spin-crossover compounds such as [Fe(pyrazine)][Pt(CN)4]·2H2O (Niel et al., 2001 ▸). However, alkali salts of polycyano­metallates are in generally water-soluble but suffer from insolubility in organic solvents. A general way to increase the solubility of metals salts in organic solvents is the utilization of crown ethers. For example, even potassium permanganate KMnO4 becomes benzene-soluble by coordination of 18-crown-6 to the potassium cation (Doheny & Ganem, 1980 ▸). During our attempts to explore the coordination chemistry of the tetra­cyano­platinate dianion [Pt(CN)4]2− in organic solvents, we realized that commercially available K2[Pt(CN)4] is insoluble in di­chloro­methane but dissolves rapidly upon addition of 18-crown-6. The product [K(18-crown-6)]2 [Pt(CN)4], which was already isolated many years ago by a rather complicated procedure (Almeida & Pidcock, 1981 ▸), could now be obtained in crystalline form. In contrast to other tetra­cyano­platinate(II) salts with large organic cations [e.g. PPh4 + (see Nast & Moerler, 1969 ▸) and NBu4 + (see Mason & Gray, 1968 ▸)], which are prepared by metathesis reactions in water, this new procedure makes the access to tetra­cyano­platinate salts with solubility in organic solvents even more facile.

Structural Commentary

[K(18-crown-6)]2 [Pt(CN)4] (Fig. 1 ▸) crystallizes in the monoclinic space group P21/n. The tetra­cyano­platinate moiety displays a square-planar mol­ecular geometry with the platinum atom lying on a crystallographic inversion centre. Two trans-orientated cyano groups coordinate via their terminal nitro­gen atoms to the potassium ions in a rather bent fashion [K1—N1—C1 = 146.76 (17)°] while the Pt—C—N bonds are almost linear [Pt1—C2—N2 = 178.81 (18)°]. The Pt—C and C—N bond lengths do not differ significantly between the terminal or bridging cyano ligands [Pt1—C2 = 1.996 (2) Å versus Pt1—C1 = 1.991 (2) Å and C2—N2 = 1.155 (3) Å versus C1—N1 = 1.154 (3) Å]. The six oxygen atoms of the crown ether coordinate to the potassium ion in a hexa­gonal-planar fashion. Additionally, one apical position is occupied by a nitro­gen atom of a cyano group, although the K—N distance is relatively long [2.732 (2) Å]. The potassium ion is located 0.295 Å above the the O6 centroid [K—O distances = 2.769 (1)–2.837 (1) Å].

Figure 1

The asymmetric unit of the title compound with displacement ellipsoids shown at the 50% probability level.

Supra­molecular features

A common feature of tetra­cyano­platinate salts is the formation of columnar stacks of the planar tetra­cyano­platinate anions with Pt⋯Pt distances in the range of 3.0–3.8 Å, see, for example, Washecheck et al. (1976 ▸), Holzapfel et al. (1981 ▸), Mühle et al. (2004 ▸) and Neuhausen et al. (2011 ▸). However, in the crystal structure of the title compound (Fig. 2 ▸), no platino­philic inter­actions are observed. This is in accordance with findings of Stojanovic et al. (2011 ▸) who stated that large organic cations can suppress the formation of Pt⋯Pt contacts. Inter­molecular inter­actions are not very pronounced in this crystal structure. However, the two uncoordinated cyano groups each point towards one neighbouring hydrogen atom in a slightly bent fashion (C—N⋯H = 152°; Table 1 ▸) although the N⋯H distance is relatively long (2.55 Å). Moreover, two hydrogen atoms from two different crown ether mol­ecules form weak contacts to the platinum atom in a linear fashion (H⋯Pt⋯H = 180°), which results in a distorted axially elongated pseudo-octa­hedral PtC4H2 coordination environment for the platinum atom. The Pt⋯H distances are slightly smaller than the sum of the van der Waals radii (2.79 Å).

Figure 2

Packing in the unit cell of the title compound.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3A⋯N1i	0.99	2.54	3.510 (3)	165
C9—H9B⋯N2ii	0.99	2.55	3.459 (3)	152

Symmetry codes: (i) ; (ii) .

Database survey

A database survey (CSD version 5.40, update of November 2018; Groom et al., 2016 ▸) gave 348 hits for the [Pt(CN)4] moiety and 1562 hits for the [K(18-crown-6)] moiety. While the tetra­cyano­platinate moiety binds to many elements from the periodic table, only a few tetra­cyano­platinate salts with metal–crown ether counter-cations are known. For example, complexes of Ba2+ [Pt(CN)4]2− with 18-crown-6 (Olmstead et al., (2005 ▸), dibenzo-18-crown-6 (Olmstead et al., 2016)) and di­aza-18-crown-6 (Olmstead et al., 2009 ▸). In the first two examples, the Ba2+ cation exhibits a coordination number of 10 whereas only ninefold coordination is observed in the last case. In general, these high coordination numbers result from bridging cyanide ligands and oxygen-containing donor solvents that bind to the Ba2+ cations. In [Tl(18-crown-6)]2[Pt(CN)4] (Liu et al., 2006 ▸), only a sevenfold coordination is observed for the thallium cation. Inter­estingly, Tl+ does not bind to a terminal cyanide group but forms a weak metallophilic contact to Pt2+ (Tl⋯Pt distance = 3.185 Å).

The combination of [K(18-crown-6)] cations with other polycyano­metallates is relatively rare. Crystal structures of [K3(18-crown-6)3(H2O)4][Cr(CN)6]·3H2O (Zhou et al., 2003 ▸), [K(18-crown-6)]2[K(18-crown-6)(H2O)2][Ru(CN)6]·CH2Cl2 (Vostrikova & Peresypkina, 2011 ▸) and [K(18-crown-6)]2[K(18-crown-6)(C3H7OH)][Os(CN)6]·2C3H7OH·H2O (Vos­tri­kova & Peresypkina, 2011 ▸) have been reported in the literature.

Synthesis and crystallization

Potassium tetra­cyano­platinate (37.7 mg, 0.1 mmol) was suspended in 3 ml of CH2Cl2. Then, 52.8 mg (0.2 mmol) of 18-crown-6 were added and the mixture was stirred for several minutes until the solid had completely dissolved. A small part of the solution was placed in a narrow glass tube and layered with diethyl ether. Colourless blocks of the title compound formed overnight. IR(ATR) (cm−1): 2898–2815 [m, v(CH)], 2126 [s, n(CN)], 1451 [w, d(CH2)], 1099 [vs, n(CO)]. 1H NMR (400 MHz in CD2Cl2): 3.62 (s, crown ether) ppm. 13C(1H) NMR (101 MHz in CD2Cl2): 122.4 (CN, 1 J Pt—C = 1018 Hz), 70.1 (crown) ppm.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2 ▸. The H atoms were placed geometrically with a constrained C—H distance of 0.99 Å and refined as riding atoms with U iso(H) = 1.2U eq(C).

Table 2

Experimental details

Crystal data
Chemical formula	[K2Pt(CN)4(C12H24O6)2]
M r	905.99
Crystal system, space group	Monoclinic, P21/n
Temperature (K)	100
a, b, c (Å)	11.7341 (10), 13.7280 (12), 11.8876 (10)
β (°)	94.999 (3)
V (Å3)	1907.6 (3)
Z	2
Radiation type	Mo Kα
μ (mm−1)	3.96
Crystal size (mm)	0.44 × 0.44 × 0.12
Data collection
Diffractometer	Bruker APEXII CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2016 ▸)
T min, T max	0.306, 0.564
No. of measured, independent and observed [I > 2σ(I)] reflections	57788, 5839, 4658
R int	0.047
(sin θ/λ)max (Å−1)	0.716
Refinement
R[F 2 > 2σ(F 2)], wR(F 2), S	0.019, 0.051, 1.05
No. of reflections	5839
No. of parameters	215
H-atom treatment	H-atom parameters constrained
Δρmax, Δρmin (e Å−3)	1.25, −1.54

Computer programs: APEX2 and SAINT (Bruker, 2016 ▸), SHELXS (Sheldrick, 2008 ▸), SHELXL2018 (Sheldrick, 2015 ▸), OLEX2 (Dolomanov et al., 2009 ▸) and publCIF (Westrip, 2010 ▸).

Crystal structure: contains datablock(s) I. DOI: 10.1107/S2056989019015238/hb4322sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989019015238/hb4322Isup2.hkl

CCDC references: 1965195, 1965195

Additional supporting information: crystallographic information; 3D view; checkCIF report

[K2Pt(CN)4(C12H24O6)2]	F(000) = 912
Mr = 905.99	Dx = 1.577 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 11.7341 (10) Å	Cell parameters from 9630 reflections
b = 13.7280 (12) Å	θ = 2.3–30.6°
c = 11.8876 (10) Å	µ = 3.96 mm−1
β = 94.999 (3)°	T = 100 K
V = 1907.6 (3) Å3	Block, colourless
Z = 2	0.44 × 0.44 × 0.12 mm

Bruker APEXII CCD diffractometer	4658 reflections with I > 2σ(I)
φ and ω scans	Rint = 0.047
Absorption correction: multi-scan (SADABS; Bruker, 2016)	θmax = 30.6°, θmin = 2.3°
Tmin = 0.306, Tmax = 0.564	h = −16→16
57788 measured reflections	k = −19→19
5839 independent reflections	l = −17→16

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.019	w = 1/[σ2(Fo2) + (0.0186P)2 + 1.9161P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.051	(Δ/σ)max = 0.001
S = 1.05	Δρmax = 1.25 e Å−3
5839 reflections	Δρmin = −1.54 e Å−3
215 parameters	Extinction correction: SHELXL2018 (Sheldrick, 2015), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
0 restraints	Extinction coefficient: 0.0120 (4)
Primary atom site location: structure-invariant direct methods

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

	x	y	z	Uiso*/Ueq
Pt1	0.500000	0.500000	0.000000	0.01307 (4)
K1	0.81107 (3)	0.50085 (2)	0.38736 (3)	0.01684 (7)
O5	0.93998 (11)	0.65091 (10)	0.29546 (12)	0.0220 (3)
O2	0.71541 (11)	0.34705 (10)	0.50409 (12)	0.0232 (3)
O4	0.97580 (12)	0.45517 (10)	0.23439 (12)	0.0256 (3)
O3	0.82893 (12)	0.31294 (10)	0.30722 (12)	0.0254 (3)
O1	0.68912 (13)	0.54392 (11)	0.57027 (12)	0.0258 (3)
O6	0.84409 (13)	0.68057 (10)	0.50316 (12)	0.0273 (3)
C2	0.34516 (17)	0.47354 (16)	0.05042 (17)	0.0234 (4)
N2	0.25437 (16)	0.45768 (17)	0.07632 (17)	0.0358 (4)
N1	0.61178 (17)	0.50228 (13)	0.25023 (17)	0.0284 (4)
C9	0.99412 (18)	0.53486 (16)	0.15999 (18)	0.0268 (4)
H9A	0.922679	0.549960	0.112661	0.032*
H9B	1.054051	0.517845	0.109679	0.032*
C1	0.56960 (16)	0.50133 (12)	0.15887 (17)	0.0192 (3)
C5	0.68672 (17)	0.26882 (14)	0.42770 (18)	0.0265 (4)
H5A	0.628172	0.290733	0.368065	0.032*
H5B	0.654414	0.214014	0.468750	0.032*
C10	1.03093 (17)	0.62118 (15)	0.23170 (19)	0.0276 (4)
H10A	1.098625	0.603787	0.283356	0.033*
H10B	1.052471	0.675460	0.182981	0.033*
C4	0.61633 (18)	0.38299 (16)	0.5518 (2)	0.0309 (4)
H4A	0.579757	0.329734	0.591811	0.037*
H4B	0.560472	0.407414	0.491136	0.037*
C6	0.79142 (17)	0.23559 (14)	0.37517 (17)	0.0250 (4)
H6A	0.852386	0.218411	0.434705	0.030*
H6B	0.773614	0.177181	0.328031	0.030*
C8	0.9510 (2)	0.36800 (15)	0.1721 (2)	0.0335 (5)
H8A	1.016517	0.350456	0.129004	0.040*
H8B	0.882998	0.377767	0.117934	0.040*
C14	0.7268 (2)	0.62271 (15)	0.64242 (18)	0.0308 (4)
H14A	0.795873	0.603522	0.691114	0.037*
H14B	0.666168	0.640928	0.691447	0.037*
C11	0.97505 (19)	0.72802 (15)	0.37123 (18)	0.0295 (4)
H11A	1.002946	0.783790	0.328515	0.035*
H11B	1.038243	0.705558	0.425670	0.035*
C12	0.8756 (2)	0.75891 (14)	0.43299 (19)	0.0311 (4)
H12A	0.896408	0.816886	0.479879	0.037*
H12B	0.810247	0.776359	0.378360	0.037*
C7	0.9286 (2)	0.28768 (15)	0.2533 (2)	0.0329 (5)
H7A	0.916538	0.225258	0.212284	0.039*
H7B	0.994834	0.280173	0.310186	0.039*
C3	0.65005 (18)	0.46399 (16)	0.63312 (18)	0.0280 (4)
H3A	0.583590	0.484034	0.673536	0.034*
H3B	0.711603	0.441769	0.689539	0.034*
C13	0.7534 (2)	0.70708 (15)	0.5689 (2)	0.0342 (5)
H13A	0.684720	0.724656	0.518624	0.041*
H13B	0.775999	0.764336	0.616299	0.041*

	U11	U22	U33	U12	U13	U23
Pt1	0.01451 (5)	0.01192 (5)	0.01299 (6)	0.00149 (3)	0.00243 (3)	−0.00065 (3)
K1	0.01690 (16)	0.01710 (16)	0.01701 (17)	−0.00121 (12)	0.00425 (13)	−0.00143 (13)
O5	0.0216 (6)	0.0192 (6)	0.0254 (7)	−0.0033 (5)	0.0037 (5)	−0.0028 (5)
O2	0.0223 (6)	0.0220 (6)	0.0260 (7)	−0.0027 (5)	0.0065 (5)	−0.0029 (5)
O4	0.0296 (7)	0.0201 (7)	0.0283 (7)	0.0010 (5)	0.0104 (6)	−0.0033 (6)
O3	0.0289 (7)	0.0185 (6)	0.0301 (8)	0.0011 (5)	0.0105 (6)	−0.0019 (5)
O1	0.0319 (7)	0.0256 (7)	0.0213 (7)	−0.0017 (6)	0.0103 (6)	−0.0027 (6)
O6	0.0382 (8)	0.0194 (6)	0.0255 (7)	−0.0025 (6)	0.0099 (6)	−0.0032 (5)
C2	0.0251 (9)	0.0275 (9)	0.0176 (8)	0.0004 (7)	0.0018 (7)	−0.0031 (7)
N2	0.0260 (9)	0.0547 (13)	0.0273 (9)	−0.0040 (9)	0.0062 (7)	−0.0055 (9)
N1	0.0228 (8)	0.0430 (11)	0.0193 (8)	0.0027 (7)	0.0013 (7)	−0.0011 (7)
C9	0.0278 (10)	0.0273 (9)	0.0272 (10)	0.0016 (8)	0.0138 (8)	0.0007 (8)
C1	0.0156 (8)	0.0228 (9)	0.0193 (8)	0.0009 (6)	0.0030 (6)	−0.0009 (6)
C5	0.0282 (10)	0.0226 (9)	0.0291 (10)	−0.0070 (7)	0.0052 (8)	−0.0030 (8)
C10	0.0202 (9)	0.0268 (9)	0.0373 (11)	−0.0026 (7)	0.0101 (8)	0.0013 (8)
C4	0.0261 (10)	0.0301 (10)	0.0390 (12)	−0.0041 (8)	0.0167 (9)	−0.0026 (9)
C6	0.0300 (10)	0.0180 (8)	0.0268 (10)	−0.0017 (7)	0.0020 (8)	−0.0013 (7)
C8	0.0426 (12)	0.0252 (10)	0.0355 (12)	−0.0025 (9)	0.0194 (10)	−0.0103 (9)
C14	0.0422 (12)	0.0276 (10)	0.0243 (10)	0.0007 (9)	0.0131 (9)	−0.0070 (8)
C11	0.0360 (11)	0.0226 (9)	0.0301 (10)	−0.0121 (8)	0.0037 (8)	−0.0037 (8)
C12	0.0475 (13)	0.0174 (9)	0.0292 (10)	−0.0060 (8)	0.0075 (9)	−0.0046 (8)
C7	0.0376 (11)	0.0207 (9)	0.0427 (13)	0.0024 (8)	0.0169 (10)	−0.0080 (9)
C3	0.0280 (10)	0.0310 (10)	0.0273 (10)	0.0011 (8)	0.0162 (8)	0.0006 (8)
C13	0.0496 (13)	0.0227 (10)	0.0322 (11)	0.0032 (9)	0.0147 (10)	−0.0070 (8)

Pt1—C2i	1.996 (2)	C9—C10	1.501 (3)
Pt1—C2	1.996 (2)	C5—H5A	0.9900
Pt1—C1i	1.991 (2)	C5—H5B	0.9900
Pt1—C1	1.991 (2)	C5—C6	1.497 (3)
K1—K1ii	4.9761 (9)	C10—H10A	0.9900
K1—O5	2.8308 (14)	C10—H10B	0.9900
K1—O2	2.8133 (14)	C4—H4A	0.9900
K1—O4	2.8369 (14)	C4—H4B	0.9900
K1—O3	2.7642 (14)	C4—C3	1.503 (3)
K1—O1	2.7691 (14)	C6—H6A	0.9900
K1—O6	2.8354 (14)	C6—H6B	0.9900
K1—N1	2.732 (2)	C8—H8A	0.9900
K1—C4	3.527 (2)	C8—H8B	0.9900
O5—C10	1.422 (2)	C8—C7	1.503 (3)
O5—C11	1.427 (2)	C14—H14A	0.9900
O2—C5	1.428 (2)	C14—H14B	0.9900
O2—C4	1.425 (2)	C14—C13	1.500 (3)
O4—C9	1.435 (3)	C11—H11A	0.9900
O4—C8	1.424 (2)	C11—H11B	0.9900
O3—C6	1.427 (2)	C11—C12	1.493 (3)
O3—C7	1.425 (2)	C12—H12A	0.9900
O1—C14	1.426 (2)	C12—H12B	0.9900
O1—C3	1.426 (3)	C7—H7A	0.9900
O6—C12	1.429 (2)	C7—H7B	0.9900
O6—C13	1.421 (3)	C3—H3A	0.9900
C2—N2	1.155 (3)	C3—H3B	0.9900
N1—C1	1.154 (3)	C13—H13A	0.9900
C9—H9A	0.9900	C13—H13B	0.9900
C9—H9B	0.9900
C2i—Pt1—C2	180.0	O2—C5—H5B	109.7
C1—Pt1—C2	91.47 (8)	O2—C5—C6	109.75 (16)
C1i—Pt1—C2i	91.47 (8)	H5A—C5—H5B	108.2
C1—Pt1—C2i	88.53 (8)	C6—C5—H5A	109.7
C1i—Pt1—C2	88.53 (8)	C6—C5—H5B	109.7
C1i—Pt1—C1	180.0	O5—C10—C9	109.71 (16)
O5—K1—K1ii	74.34 (3)	O5—C10—H10A	109.7
O5—K1—O4	59.78 (4)	O5—C10—H10B	109.7
O5—K1—O6	59.94 (4)	C9—C10—H10A	109.7
O5—K1—C4	160.31 (5)	C9—C10—H10B	109.7
O2—K1—K1ii	96.09 (3)	H10A—C10—H10B	108.2
O2—K1—O5	170.43 (4)	K1—C4—H4A	159.0
O2—K1—O4	118.28 (4)	K1—C4—H4B	82.0
O2—K1—O6	117.20 (4)	O2—C4—K1	49.29 (9)
O2—K1—C4	22.59 (4)	O2—C4—H4A	109.8
O4—K1—K1ii	73.68 (3)	O2—C4—H4B	109.8
O4—K1—C4	139.85 (5)	O2—C4—C3	109.49 (17)
O3—K1—K1ii	95.19 (3)	H4A—C4—H4B	108.2
O3—K1—O5	119.15 (4)	C3—C4—K1	82.54 (11)
O3—K1—O2	61.00 (4)	C3—C4—H4A	109.8
O3—K1—O4	59.77 (4)	C3—C4—H4B	109.8
O3—K1—O1	121.99 (4)	O3—C6—C5	108.32 (16)
O3—K1—O6	165.50 (5)	O3—C6—H6A	110.0
O3—K1—C4	80.51 (5)	O3—C6—H6B	110.0
O1—K1—K1ii	94.33 (3)	C5—C6—H6A	110.0
O1—K1—O5	118.53 (4)	C5—C6—H6B	110.0
O1—K1—O2	61.13 (4)	H6A—C6—H6B	108.4
O1—K1—O4	167.99 (5)	O4—C8—H8A	109.9
O1—K1—O6	59.40 (4)	O4—C8—H8B	109.9
O1—K1—C4	42.15 (5)	O4—C8—C7	108.77 (18)
O6—K1—K1ii	70.44 (3)	H8A—C8—H8B	108.3
O6—K1—O4	115.57 (4)	C7—C8—H8A	109.9
O6—K1—C4	101.40 (5)	C7—C8—H8B	109.9
N1—K1—K1ii	175.95 (5)	O1—C14—H14A	110.2
N1—K1—O5	102.88 (5)	O1—C14—H14B	110.2
N1—K1—O2	86.68 (5)	O1—C14—C13	107.71 (17)
N1—K1—O4	102.40 (5)	H14A—C14—H14B	108.5
N1—K1—O3	83.55 (5)	C13—C14—H14A	110.2
N1—K1—O1	89.59 (5)	C13—C14—H14B	110.2
N1—K1—O6	110.92 (5)	O5—C11—H11A	109.9
N1—K1—C4	76.81 (6)	O5—C11—H11B	109.9
C4—K1—K1ii	106.82 (4)	O5—C11—C12	109.03 (17)
C10—O5—K1	116.61 (11)	H11A—C11—H11B	108.3
C10—O5—C11	111.15 (15)	C12—C11—H11A	109.9
C11—O5—K1	115.51 (11)	C12—C11—H11B	109.9
C5—O2—K1	109.45 (11)	O6—C12—C11	109.03 (17)
C4—O2—K1	108.12 (11)	O6—C12—H12A	109.9
C4—O2—C5	110.99 (15)	O6—C12—H12B	109.9
C9—O4—K1	111.94 (11)	C11—C12—H12A	109.9
C8—O4—K1	113.54 (11)	C11—C12—H12B	109.9
C8—O4—C9	110.80 (17)	H12A—C12—H12B	108.3
C6—O3—K1	117.58 (11)	O3—C7—C8	107.85 (17)
C7—O3—K1	118.16 (11)	O3—C7—H7A	110.1
C7—O3—C6	112.30 (15)	O3—C7—H7B	110.1
C14—O1—K1	118.68 (12)	C8—C7—H7A	110.1
C3—O1—K1	117.32 (11)	C8—C7—H7B	110.1
C3—O1—C14	111.44 (16)	H7A—C7—H7B	108.4
C12—O6—K1	113.75 (11)	O1—C3—C4	108.13 (17)
C13—O6—K1	114.36 (12)	O1—C3—H3A	110.1
C13—O6—C12	111.85 (16)	O1—C3—H3B	110.1
N2—C2—Pt1	177.97 (18)	C4—C3—H3A	110.1
C1—N1—K1	146.76 (17)	C4—C3—H3B	110.1
O4—C9—H9A	110.2	H3A—C3—H3B	108.4
O4—C9—H9B	110.2	O6—C13—C14	109.05 (17)
O4—C9—C10	107.64 (17)	O6—C13—H13A	109.9
H9A—C9—H9B	108.5	O6—C13—H13B	109.9
C10—C9—H9A	110.2	C14—C13—H13A	109.9
C10—C9—H9B	110.2	C14—C13—H13B	109.9
N1—C1—Pt1	178.81 (18)	H13A—C13—H13B	108.3
O2—C5—H5A	109.7

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3A···N1iii	0.99	2.54	3.510 (3)	165
C9—H9B···N2iv	0.99	2.55	3.459 (3)	152