A new [(1R,2R)-1,2-diamino­cyclo­hexane]platinum(II) complex: formation by nitrate–acetonitrile ligand exchange

The title compound, cis-diacetonitrile­[(1R,2R)-1,2-diamino­cyclo­hexane-κ²N,N′]platinum(II) dinitrate monohydrate, [Pt(C₂H₃N)₂(C₆H₁₄N₂)](NO₃)₂·H₂O, is a mol­ecular salt of the diamino­cyclo­hexane–Pt complex cation. There are two formula units in the asymmetric unit. Apart from the two charge-balancing nitrate anions, one neutral mol­ecule of water is present. The components inter­act via N—H...O and O—H...O hydrogen bonds, resulting in supra­molecular chains. The title compound crystallizes only from acetonitrile with residual water, with the acetonitrile coordinating to the mol­ecule of cis-[Pt(NO₃)₂(DACH)] (DACH is 1,2-diamino­cyclo­hexane) and the water forming a monohydrate.

S1. Comment

The search for novel platinum-based anticancer complexes remains one of the expanding areas of the contemporary pharmaceutical industry. The driving force in this group of active anticancer therapeutics is the discovery of more active and less toxic analogues of the chemotherapy complexes used in today's clinical practice (cisplatin, carboplatin, oxaliplatin etc.) (Ho et al., 2003; Galanski et al., 2003; Abu-Surrah & Kettunen, 2006). Some of the novel structures are based on the platinum (1R,2R)-1,2-diaminocyclohexane (DACH) carrier ligand and various leaving groups bound to the central Pt metal atom. There are several synthetic routes used for the preparation of DACH–platinum-based complexes (Fuertes et al., 2004; Leh & Wolf, 1976). One of the interesting routes for the preparation of oxaliplatin, AP5346 and other DACH–Pt complexes is the synthetic method starting from cis-[Pt(DACH)(NO₃)₂]. This compound is a valuable precursor of the DACH–Pt-based cytostatics (Pasini et al., 1993). This is prepared by a simple method where cis-[Pt(DACH)Cl₂], prepared by the quantitative transformation of DACH with K₂[PtCl₄], reacts with silver nitrate. The title compound, (I), crystallizes only from acetonitrile with residual water in such a way that the molecule forms a monohydrate.

The single-crystal structure of (I) is built up from discrete molecules in the monoclinic space group P2₁, with two molecules in the asymmetric unit. The [Pt(C₂H₃N)₂(C₆H₁₄N₂)]²⁺ complex cation is formed by one cyclohexane ring with a chair conformation, a five-membered diamine ring with a central Pt atom and two leaving groups of acetonitrile (N≡ C—CH₃). This dication is balanced by two nitrate groups and one neutral water molecule.

The [Pt(C₂H₃N)₂(C₆H₁₄N₂)]²⁺ cation is nearly planar, with the dihedral angle between the N1A—N2A—N3A—N4A plane and the cyclohexane plane (C3A—C6A—N1A—N2A) being 4.96°, unlike some other known DACH structures, such as cis-[Pt(DACH)Br₂] or cis-[Pt(DACH)Cl₂], where dihedral angles are between 50 and 70° (Lock & Pilon, 1981). The Pt—N1A bond is shorter than the same bond in cis-[Pt(DACH)Br₂] and similar to that in cis-[Pt(DACH)Cl₂] (Lock & Pilon, 1981). As for the two cations, they show few significant differences in bond distances and angles, apart from the analogous Pt1—N3—C7 angle which is 178.6 (3)° (molecule A) and 174.1 (3)° (molecule B). Comparable torsion angles about the Pt atoms, e.g. N4—Pt1—N2—C2, differ by up to 8° in molecules A and B. The N—O bonds in the NO₃ group lie within expected ranges and these nitrate groups are positioned in such a manner that the O atoms of the NO₃ group are oriented towards the H atoms of the water and the diamine group, forming hydrogen bonds.

There are three systems of supramolecular chains interacting by hydrogen bonds: one formed by bifurcated N—H···(O,O) interactions linking an N atom of the diamine group with O atoms of the nitrate group, and two bifurcated O—H···(O,O) chains linking an O atom of the nitrate group to the water O atom. The first is parallel to [001] (c axis) and takes the form (O1B,O3B)ⁱⁱⁱ–N2Aⁱ–(O2A,O3A)–N5A–(O1A,O3A)–N2B^iv –(O2B,O3B)^vi–(O1B,O3B)^vi when viewed down the b axis (Fig. 1) [Fig. 2?]. Also present are chains parallel to [010] (b axis) (Fig. 3) between the water molecule and nitrate groups, of the form O5A–N6A–(O4A,O6A)–O7A–O5Aⁱⁱⁱ when viewed down the c axis; the second chain running parallel to the b axis is O5B^vi–O7B–(O4B,O6B)–N6B–O5B. Details of hydrogen bonds are given in Table 1 and the C—H···O interactions are considered weak.

S2. Experimental

The title compound was prepared using the following procedure. An aqueous suspension (312 ml) of cis-[Pt(DACH)Cl₂] (0.041 mol, 15.6 g) was mixed with 1.935 equivalents of AgNO₃ (0.079 mol, 13.5 g) and the reaction mixture was stirred in the absence of light at 318 K for 4 h. The by-product, AgCl, was removed by filtration through an ultra-filter (Ø 0.22 mm; Sigma–Aldrich) and a layer of active carbon. The colourless filtrate was evaporated and dried (Buchi Rotavapor RII rotary evaporator, 318 K, 2 kPa). The resulting white powder, crude cis-[Pt(DACH)(NO₃)₂], was recrystallized from acetonitrile. Single crystals of cis-[Pt(CH₃CN)₂(DACH)](NO₃)₂.H₂O, (I), suitable for X-ray diffraction analysis, were obtained from a solution of cis-[Pt(DACH)(NO₃)₂] (3.1 mg, 0.0072 mmol) in acetonitrile (0.24 ml) by spontaneous precipitation under slow programmed cooling.

S3. Refinement

The title structure exhibits strong pseudo-symmetry in space group P2₁/c. Using this symmetry, the cyclohexane ring showed disorder. After refinement in this space group, the R factors converged to 0.042, but large anisotropic displacement parameters (ADPs) were shown by the NO₃ atoms and three of the six C atoms of the cyclohexane ring. These C atoms were split and the ADPs changed to isotropic, and two chairs appeared with the refinement converging to 0.039 and goodness-of-fit 0.023. However, the H atoms of the water molecule and diamine groups were not visible in the difference Fourier map. Therefore, the sample was remeasured at a lower temperature, which showed that the reflections violating the c-glide plane were real violations, not admixtures present in low-quality data. Therefore, the model was transformed to subgroup P2₁. For expansion of the structure model, the inversion was used as a merohedric twinning operation. In this case the volume fraction of the inversion twin is the Flack parameter (Flack, 1983). This parameter refined to a final value of 0.027 (5), which confirms both that the above configuration is the correct absolute structure and that there is no twinning in the crystal structure. The noncentrosymmetric refinement converged to R factors close to 0.01, reasonable ADPs of the C atoms in the cyclohexane ring and all H atoms visible in the difference Fourier maps. There are no significant differences between the individual cations in space groups P2₁ and P2₁/c, apart from the disorder of the C atoms in the cyclohexane ring shown in P2₁/c which is non-existent in P2₁. As to the two cations in the asymmetric unit in P2₁, they show few significant differences in bond distances and angles, but several are noted for the torsion angles.

O- and N-bound H atoms were refined, with N—H restrained to 0.87 (2) Å and O—H restrained to 0.80 (3) Å. All other H atoms were positioned geometrically and refined using a riding model, with C—H = 0.96 Å and with U_iso(H) = 1.2U_eq(C).

Computing details

Data collection: CrysAlis CCD (Oxford Diffraction, 2008); cell refinement: CrysAlis RED (Oxford Diffraction, 2008); data reduction: CrysAlis RED (Oxford Diffraction, 2008); program(s) used to solve structure: SUPERFLIP (Palatinus & Chapuis, 2007); program(s) used to refine structure: JANA2006 (Petříček et al., 2006); molecular graphics: ORTEP-3 (Farrugia, 1999) and Mercury (Version 2.3; Macrae et al., 2006); software used to prepare material for publication: JANA2006 (Petříček et al., 2006).

Figures

	Fig. 1. The molecular structure of (I), with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level and H atoms are shown as small spheres of arbitrary radii.
	Fig. 2. Bifurcated hydrogen-bonded chains formed by N—H···(O,O) interactions along the c axis. H atoms not involved have been omitted for clarity.
	Fig. 3. The formation of two types of hydrogen-bonded chains parallel to the b axis.

cis-diacetonitrile[(1R,2R)-1,2-diaminocyclohexane- κ²N,N']platinum(II) dinitrate monohydrate

Crystal data

[Pt(C2H3N)2(C6H14N2)](NO3)2·H2O	F(000) = 1032
Mr = 533.4	Dx = 1.994 Mg m^−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 14954 reflections
a = 12.6799 (3) Å	θ = 2.8–28.3°
b = 12.0326 (3) Å	µ = 7.94 mm^−1
c = 11.6791 (2) Å	T = 120 K
β = 94.5495 (17)°	Block, colourless
V = 1776.29 (7) Å^3	0.49 × 0.20 × 0.10 mm
Z = 4

Data collection

Oxford Xcalibur Atlas Gemini Ultra diffractometer	7866 independent reflections
Radiation source: X-ray tube	7374 reflections with I > 3σ(I)
Unknown monochromator	Rint = 0.014
Detector resolution: 10.3784 pixels mm^-1	θmax = 28.3°, θmin = 2.8°
ω scans	h = −16→16
Absorption correction: analytical [CrysAlis PRO (Oxford Diffraction, 2008; Clark & Reid, 1995)]	k = −15→15
Tmin = 0.110, Tmax = 0.544	l = −15→15
16828 measured reflections

Refinement

Refinement on F^2	H atoms treated by a mixture of independent and constrained refinement
R[F > 3σ(F)] = 0.012	Weighting scheme based on measured s.u.'s w = 1/[σ^2(I) + 0.0004I^2]
wR(F) = 0.030	(Δ/σ)max = 0.046
S = 1.02	Δρmax = 0.34 e Å^−3
7866 reflections	Δρmin = −0.18 e Å^−3
480 parameters	Absolute structure: Flack (1983), with 3554 Friedel pairs
12 restraints	Absolute structure parameter: 0.027 (5)
129 constraints

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

	x	y	z	Uiso*/Ueq
Pt1A	0.164710 (9)	0.632731	0.694934 (7)	0.01606 (4)
Pt1B	0.834036 (9)	0.367277 (8)	0.812672 (7)	0.01626 (4)
O1A	0.0643 (2)	0.2325 (3)	0.63327 (19)	0.0345 (9)
O1B	0.9214 (2)	0.7597 (2)	0.85663 (19)	0.0290 (8)
N6A	0.5244 (2)	0.6448 (3)	0.5943 (2)	0.0272 (9)
N6B	0.4834 (2)	0.3710 (4)	0.9117 (2)	0.0264 (9)
O2A	0.0855 (2)	0.3163 (3)	0.47192 (19)	0.0348 (9)
O2B	0.9037 (2)	0.6925 (2)	1.02632 (18)	0.0326 (9)
N2A	0.1038 (2)	0.7847 (3)	0.7220 (2)	0.0183 (9)
N2B	0.8951 (2)	0.2146 (3)	0.7899 (2)	0.0176 (9)
C8A	0.3288 (3)	0.3007 (3)	0.6382 (3)	0.0369 (13)
C8B	0.6592 (3)	0.6910 (3)	0.8741 (3)	0.0333 (12)
N1A	0.3035 (3)	0.7046 (3)	0.7512 (2)	0.0210 (10)
N1B	0.6977 (2)	0.2982 (2)	0.7449 (2)	0.0183 (9)
O4A	0.5931 (2)	0.6122 (3)	0.5315 (2)	0.0410 (10)
O4B	0.3996 (3)	0.3973 (3)	0.9473 (3)	0.0672 (14)
C6A	0.3810 (3)	0.8923 (3)	0.8032 (3)	0.0288 (12)
C6B	0.6238 (3)	0.1130 (3)	0.6787 (2)	0.0236 (10)
C3A	0.1612 (3)	0.9785 (3)	0.7805 (3)	0.0250 (12)
C3B	0.8407 (3)	0.0226 (3)	0.7214 (3)	0.0238 (11)
O5A	0.5096 (3)	0.7450 (3)	0.6105 (2)	0.0536 (12)
O5B	0.5004 (3)	0.2716 (3)	0.8817 (2)	0.0400 (9)
O3A	−0.0694 (2)	0.3084 (3)	0.53597 (19)	0.0328 (9)
O3B	1.0573 (2)	0.6882 (2)	0.95542 (17)	0.0262 (8)
C4A	0.2533 (3)	1.0452 (3)	0.8383 (2)	0.0281 (10)
C4B	0.7447 (3)	−0.0545 (3)	0.7001 (3)	0.0279 (10)
N3A	0.2331 (2)	0.4863 (3)	0.6716 (2)	0.0212 (10)
N3B	0.7650 (2)	0.5128 (3)	0.8332 (2)	0.0209 (10)
C7A	0.2735 (3)	0.4047 (3)	0.6581 (3)	0.0249 (11)
C7B	0.7191 (3)	0.5919 (3)	0.8503 (2)	0.0209 (11)
N5A	0.0274 (3)	0.2875 (3)	0.5462 (2)	0.0252 (10)
N5B	0.9605 (3)	0.7129 (3)	0.9461 (2)	0.0219 (9)
O7A	0.6206 (2)	0.3849 (3)	0.5308 (2)	0.0325 (9)
O7B	0.3664 (2)	0.6285 (3)	0.98147 (18)	0.0284 (7)
N4A	0.0220 (2)	0.5784 (3)	0.6364 (2)	0.0203 (9)
N4B	0.9733 (3)	0.4210 (3)	0.8770 (2)	0.0214 (9)
C9A	−0.0620 (3)	0.5645 (3)	0.6008 (2)	0.0200 (10)
C9B	1.0588 (3)	0.4373 (3)	0.9133 (2)	0.0212 (11)
C10A	−0.1710 (3)	0.5519 (3)	0.5536 (3)	0.0273 (11)
C10B	1.1674 (3)	0.4530 (3)	0.9599 (3)	0.0243 (11)
C1A	0.2910 (2)	0.8275 (2)	0.7408 (2)	0.0193 (8)
C1B	0.7213 (2)	0.1879 (2)	0.6948 (2)	0.0184 (8)
C2A	0.1853 (2)	0.8555 (2)	0.7870 (2)	0.0189 (8)
C2B	0.8065 (2)	0.1338 (2)	0.7711 (2)	0.0170 (7)
C5A	0.3585 (2)	1.0169 (2)	0.7917 (3)	0.0323 (10)
C5B	0.6548 (2)	0.0020 (2)	0.6263 (3)	0.0296 (10)
O6A	0.4723 (3)	0.5750 (3)	0.6417 (3)	0.0668 (12)
O6B	0.5544 (2)	0.4383 (3)	0.9073 (3)	0.0607 (12)
H1C8A	0.375985	0.283549	0.704164	0.0442*
H2C8A	0.278145	0.241852	0.625316	0.0442*
H3C8A	0.368535	0.308519	0.572029	0.0442*
H1C8B	0.700211	0.736716	0.928379	0.04*
H2C8B	0.643562	0.731855	0.804196	0.04*
H3C8B	0.594414	0.670054	0.905481	0.04*
H1C6A	0.446008	0.875306	0.77005	0.0345*
H2C6A	0.386907	0.87206	0.883012	0.0345*
H1C6B	0.570665	0.148635	0.628286	0.0283*
H2C6B	0.596494	0.099862	0.751877	0.0283*
H1C3A	0.098138	0.993462	0.818226	0.03*
H2C3A	0.149532	1.00045	0.701448	0.03*
H1C3B	0.892291	−0.012055	0.774391	0.0285*
H2C3B	0.871787	0.035601	0.65031	0.0285*
H1C4A	0.239471	1.123199	0.828273	0.0337*
H2C4A	0.257772	1.032148	0.919585	0.0337*
H1C4B	0.719841	−0.076184	0.772337	0.0335*
H2C4B	0.765637	−0.120961	0.662528	0.0335*
H1C10A	−0.186136	0.474593	0.540365	0.0328*
H2C10A	−0.217799	0.58114	0.606871	0.0328*
H3C10A	−0.181036	0.591733	0.482306	0.0328*
H1C10B	1.1886	0.528311	0.947215	0.0291*
H2C10B	1.172653	0.437807	1.040843	0.0291*
H3C10B	1.212864	0.403235	0.922426	0.0291*
H1C1A	0.292759	0.849094	0.661826	0.0231*
H1C1B	0.744201	0.19927	0.619259	0.0221*
H1C2A	0.186315	0.83935	0.867599	0.0227*
H1C2B	0.781113	0.115182	0.843996	0.0204*
H1C5A	0.356725	1.037958	0.712295	0.0388*
H2C5A	0.41403	1.057833	0.833404	0.0388*
H1C5B	0.676456	0.014516	0.550483	0.0355*
H2C5B	0.594325	−0.046228	0.619253	0.0355*
H1N2A	0.0841 (19)	0.809 (2)	0.6536 (9)	−0.003 (6)*
H1N2B	0.933 (2)	0.217 (3)	0.7308 (18)	0.030 (10)*
H2N2A	0.0473 (12)	0.781 (3)	0.759 (2)	0.010 (7)*
H1N1A	0.328 (2)	0.678 (3)	0.8172 (13)	0.009 (8)*
H1O7A	0.581 (3)	0.347 (3)	0.491 (3)	0.036 (12)*
H2N2B	0.930 (3)	0.200 (4)	0.855 (2)	0.078 (17)*
H1N1B	0.663 (3)	0.286 (3)	0.805 (2)	0.054 (13)*
H2O7A	0.594 (3)	0.4446 (14)	0.539 (3)	0.033 (11)*
H2N1A	0.3603 (13)	0.689 (3)	0.717 (2)	0.019 (8)*
H2N1B	0.680 (4)	0.321 (5)	0.675 (2)	0.09 (2)*
H1O7B	0.404 (2)	0.670 (3)	1.019 (3)	0.039 (12)*
H2O7B	0.381 (3)	0.5639 (9)	0.981 (3)	0.031 (11)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Pt1A	0.01677 (8)	0.01570 (9)	0.01556 (5)	−0.00101 (6)	0.00036 (4)	−0.00043 (5)
Pt1B	0.01640 (8)	0.01584 (9)	0.01622 (5)	−0.00146 (6)	−0.00077 (4)	−0.00084 (5)
O1A	0.0386 (17)	0.0417 (17)	0.0231 (11)	0.0115 (13)	0.0028 (10)	0.0097 (10)
O1B	0.0218 (13)	0.0367 (16)	0.0282 (11)	0.0035 (11)	0.0012 (9)	0.0091 (10)
N6A	0.0208 (15)	0.031 (2)	0.0284 (12)	0.0019 (14)	−0.0070 (10)	−0.0030 (13)
N6B	0.0232 (16)	0.0275 (17)	0.0282 (12)	−0.0004 (14)	0.0009 (10)	0.0031 (13)
O2A	0.0379 (17)	0.0407 (18)	0.0263 (11)	−0.0098 (13)	0.0068 (10)	0.0019 (11)
O2B	0.0380 (17)	0.0346 (16)	0.0272 (11)	−0.0082 (12)	0.0155 (11)	0.0026 (10)
N2A	0.0186 (16)	0.0206 (17)	0.0159 (11)	−0.0005 (13)	0.0018 (10)	0.0011 (10)
N2B	0.0169 (16)	0.0175 (16)	0.0179 (12)	0.0006 (12)	−0.0024 (10)	−0.0018 (10)
C8A	0.039 (2)	0.029 (2)	0.0409 (19)	0.0115 (18)	−0.0090 (16)	−0.0061 (16)
C8B	0.042 (2)	0.0192 (19)	0.0396 (18)	0.0076 (16)	0.0096 (16)	0.0039 (14)
N1A	0.0161 (18)	0.029 (2)	0.0180 (12)	0.0017 (14)	0.0004 (11)	−0.0011 (11)
N1B	0.0203 (18)	0.0133 (16)	0.0207 (13)	−0.0015 (13)	−0.0021 (11)	−0.0014 (11)
O4A	0.0310 (16)	0.0392 (19)	0.0552 (14)	0.0032 (14)	0.0185 (12)	0.0115 (14)
O4B	0.0302 (19)	0.041 (2)	0.136 (3)	0.0083 (15)	0.0372 (18)	0.000 (2)
C6A	0.020 (2)	0.030 (2)	0.0370 (16)	−0.0058 (16)	0.0045 (13)	−0.0079 (15)
C6B	0.0189 (18)	0.023 (2)	0.0278 (14)	−0.0011 (15)	−0.0046 (11)	−0.0053 (13)
C3A	0.025 (2)	0.024 (2)	0.0259 (16)	0.0044 (17)	0.0055 (14)	−0.0033 (14)
C3B	0.026 (2)	0.016 (2)	0.0287 (16)	−0.0015 (16)	0.0023 (14)	−0.0028 (13)
O5A	0.087 (3)	0.0311 (17)	0.0403 (14)	0.0198 (17)	−0.0077 (15)	−0.0047 (12)
O5B	0.0477 (18)	0.0298 (16)	0.0406 (13)	0.0188 (13)	−0.0074 (12)	−0.0036 (11)
O3A	0.0292 (16)	0.0396 (17)	0.0287 (11)	0.0064 (12)	−0.0032 (10)	−0.0063 (10)
O3B	0.0260 (15)	0.0269 (15)	0.0250 (10)	0.0048 (11)	−0.0024 (9)	0.0012 (9)
C4A	0.0349 (19)	0.0192 (16)	0.0313 (16)	−0.0029 (13)	0.0097 (14)	−0.0071 (13)
C4B	0.0289 (19)	0.0187 (16)	0.0359 (17)	−0.0027 (13)	0.0014 (14)	−0.0037 (13)
N3A	0.0201 (18)	0.0199 (19)	0.0237 (13)	−0.0007 (14)	0.0024 (11)	−0.0010 (11)
N3B	0.0220 (19)	0.0190 (19)	0.0210 (13)	−0.0037 (14)	−0.0036 (11)	0.0003 (11)
C7A	0.028 (2)	0.023 (2)	0.0232 (14)	−0.0034 (17)	−0.0001 (13)	0.0000 (13)
C7B	0.0215 (19)	0.022 (2)	0.0191 (13)	−0.0026 (15)	0.0013 (12)	0.0008 (12)
N5A	0.0311 (19)	0.0244 (18)	0.0202 (12)	−0.0011 (14)	0.0024 (11)	−0.0051 (11)
N5B	0.0286 (17)	0.0137 (16)	0.0234 (12)	−0.0006 (12)	0.0021 (11)	−0.0001 (10)
O7A	0.0331 (15)	0.0289 (18)	0.0338 (12)	0.0044 (13)	−0.0087 (10)	−0.0007 (12)
O7B	0.0295 (14)	0.0222 (13)	0.0322 (11)	−0.0026 (12)	−0.0058 (9)	−0.0011 (12)
N4A	0.0201 (17)	0.0168 (16)	0.0239 (12)	−0.0018 (12)	0.0015 (11)	−0.0001 (10)
N4B	0.0237 (18)	0.0166 (16)	0.0234 (12)	−0.0019 (13)	−0.0003 (11)	0.0013 (11)
C9A	0.023 (2)	0.0157 (18)	0.0208 (13)	−0.0020 (14)	0.0024 (12)	−0.0002 (11)
C9B	0.028 (2)	0.0166 (18)	0.0192 (13)	−0.0005 (15)	0.0036 (13)	0.0008 (11)
C10A	0.024 (2)	0.031 (2)	0.0271 (15)	−0.0023 (16)	−0.0027 (13)	−0.0003 (14)
C10B	0.0179 (19)	0.026 (2)	0.0288 (15)	−0.0034 (15)	0.0004 (12)	0.0014 (14)
C1A	0.0236 (15)	0.0183 (13)	0.0164 (12)	−0.0018 (10)	0.0044 (11)	−0.0012 (10)
C1B	0.0211 (15)	0.0161 (13)	0.0180 (13)	−0.0024 (10)	0.0016 (10)	−0.0033 (10)
C2A	0.0182 (13)	0.0220 (14)	0.0167 (11)	−0.0050 (10)	0.0021 (10)	−0.0021 (12)
C2B	0.0181 (13)	0.0164 (12)	0.0166 (11)	−0.0019 (10)	0.0023 (9)	−0.0021 (12)
C5A	0.0314 (17)	0.0231 (16)	0.0439 (18)	−0.0116 (12)	0.0118 (15)	−0.0109 (13)
C5B	0.0290 (17)	0.0250 (16)	0.0340 (17)	−0.0073 (12)	−0.0021 (13)	−0.0085 (13)
O6A	0.065 (2)	0.057 (2)	0.086 (2)	−0.0322 (17)	0.0487 (18)	−0.0302 (17)
O6B	0.0420 (18)	0.062 (2)	0.080 (2)	−0.0274 (15)	0.0193 (16)	−0.0110 (17)

Geometric parameters (Å, º)

Pt1A—N2A	2.019 (3)	C6B—H1C6B	0.96
Pt1A—N1A	2.023 (3)	C6B—H2C6B	0.96
Pt1A—N3A	1.992 (3)	C3A—C4A	1.530 (5)
Pt1A—N4A	1.993 (3)	C3A—C2A	1.512 (5)
Pt1B—N2B	2.019 (3)	C3A—H1C3A	0.96
Pt1B—N1B	2.022 (3)	C3A—H2C3A	0.96
Pt1B—N3B	1.981 (3)	C3B—C4B	1.535 (5)
Pt1B—N4B	1.972 (3)	C3B—C2B	1.534 (4)
O1A—N5A	1.271 (4)	C3B—H1C3B	0.96
O1B—N5B	1.255 (4)	C3B—H2C3B	0.96
N6A—O4A	1.246 (4)	O3A—N5A	1.249 (4)
N6A—O5A	1.237 (5)	O3B—N5B	1.258 (4)
N6A—O6A	1.229 (5)	C4A—C5A	1.518 (5)
N6B—O4B	1.213 (5)	C4A—H1C4A	0.96
N6B—O5B	1.270 (5)	C4A—H2C4A	0.96
N6B—O6B	1.215 (5)	C4B—C5B	1.533 (4)
O2A—N5A	1.231 (4)	C4B—H1C4B	0.96
O2B—N5B	1.250 (4)	C4B—H2C4B	0.96
N2A—C2A	1.499 (4)	N3A—C7A	1.124 (5)
N2A—H1N2A	0.870 (14)	N3B—C7B	1.141 (5)
N2A—H2N2A	0.87 (2)	O7A—H1O7A	0.80 (3)
N2B—C2B	1.489 (4)	O7A—H2O7A	0.80 (2)
N2B—H1N2B	0.87 (3)	O7B—H1O7B	0.80 (3)
N2B—H2N2B	0.87 (3)	O7B—H2O7B	0.800 (14)
C8A—C7A	1.462 (6)	N4A—C9A	1.125 (5)
C8A—H1C8A	0.96	N4B—C9B	1.149 (5)
C8A—H2C8A	0.96	C9A—C10A	1.455 (5)
C8A—H3C8A	0.96	C9B—C10B	1.454 (5)
C8B—C7B	1.452 (6)	C10A—H1C10A	0.96
C8B—H1C8B	0.96	C10A—H2C10A	0.96
C8B—H2C8B	0.96	C10A—H3C10A	0.96
C8B—H3C8B	0.96	C10B—H1C10B	0.96
N1A—C1A	1.492 (4)	C10B—H2C10B	0.96
N1A—H1N1A	0.870 (19)	C10B—H3C10B	0.96
N1A—H2N1A	0.87 (2)	C1A—C2A	1.521 (4)
N1B—C1B	1.490 (4)	C1A—H1C1A	0.96
N1B—H1N1B	0.87 (3)	C1B—C2B	1.495 (4)
N1B—H2N1B	0.87 (3)	C1B—H1C1B	0.96
C6A—C1A	1.520 (4)	C2A—H1C2A	0.96
C6A—C5A	1.531 (5)	C2B—H1C2B	0.96
C6A—H1C6A	0.96	C5A—H1C5A	0.96
C6A—H2C6A	0.96	C5A—H2C5A	0.96
C6B—C1B	1.529 (5)	C5B—H1C5B	0.96
C6B—C5B	1.533 (5)	C5B—H2C5B	0.96
N2A—Pt1A—N1A	84.03 (13)	H1C3B—C3B—H2C3B	108.7835
N2A—Pt1A—N3A	176.63 (12)	C3A—C4A—C5A	112.7 (3)
N2A—Pt1A—N4A	90.14 (12)	C3A—C4A—H1C4A	109.4715
N1A—Pt1A—N3A	92.60 (13)	C3A—C4A—H2C4A	109.4714
N1A—Pt1A—N4A	173.85 (13)	C5A—C4A—H1C4A	109.4714
N3A—Pt1A—N4A	93.23 (12)	C5A—C4A—H2C4A	109.4704
N2B—Pt1B—N1B	84.21 (12)	H1C4A—C4A—H2C4A	106.0307
N2B—Pt1B—N3B	176.32 (12)	C3B—C4B—C5B	111.6 (3)
N2B—Pt1B—N4B	90.43 (12)	C3B—C4B—H1C4B	109.4707
N1B—Pt1B—N3B	92.20 (12)	C3B—C4B—H2C4B	109.4713
N1B—Pt1B—N4B	174.63 (13)	C5B—C4B—H1C4B	109.4715
N3B—Pt1B—N4B	93.16 (13)	C5B—C4B—H2C4B	109.4711
O4A—N6A—O5A	121.3 (4)	H1C4B—C4B—H2C4B	107.2691
O4A—N6A—O6A	118.5 (4)	Pt1A—N3A—C7A	178.6 (3)
O5A—N6A—O6A	120.3 (3)	Pt1B—N3B—C7B	174.1 (3)
O4B—N6B—O5B	120.8 (4)	C8A—C7A—N3A	178.0 (4)
O4B—N6B—O6B	120.9 (4)	C8B—C7B—N3B	178.6 (4)
O5B—N6B—O6B	118.2 (3)	O1A—N5A—O2A	120.5 (3)
Pt1A—N2A—C2A	109.7 (2)	O1A—N5A—O3A	118.5 (3)
Pt1A—N2A—H1N2A	104.6 (16)	O2A—N5A—O3A	120.9 (3)
Pt1A—N2A—H2N2A	112 (2)	O1B—N5B—O2B	119.9 (3)
C2A—N2A—H1N2A	114.1 (17)	O1B—N5B—O3B	119.8 (3)
C2A—N2A—H2N2A	109.6 (17)	O2B—N5B—O3B	120.3 (3)
H1N2A—N2A—H2N2A	107 (2)	H1O7A—O7A—H2O7A	109 (3)
Pt1B—N2B—C2B	108.75 (19)	H1O7B—O7B—H2O7B	119 (3)
Pt1B—N2B—H1N2B	108 (3)	Pt1A—N4A—C9A	169.4 (3)
Pt1B—N2B—H2N2B	104 (3)	Pt1B—N4B—C9B	170.5 (3)
C2B—N2B—H1N2B	111 (2)	N4A—C9A—C10A	177.4 (4)
C2B—N2B—H2N2B	109 (3)	N4B—C9B—C10B	177.6 (4)
H1N2B—N2B—H2N2B	116 (3)	C9A—C10A—H1C10A	109.4709
C7A—C8A—H1C8A	109.4713	C9A—C10A—H2C10A	109.4716
C7A—C8A—H2C8A	109.4709	C9A—C10A—H3C10A	109.4711
C7A—C8A—H3C8A	109.4712	H1C10A—C10A—H2C10A	109.4706
H1C8A—C8A—H2C8A	109.4715	H1C10A—C10A—H3C10A	109.4717
H1C8A—C8A—H3C8A	109.4716	H2C10A—C10A—H3C10A	109.4714
H2C8A—C8A—H3C8A	109.4708	C9B—C10B—H1C10B	109.4703
C7B—C8B—H1C8B	109.4712	C9B—C10B—H2C10B	109.4709
C7B—C8B—H2C8B	109.4712	C9B—C10B—H3C10B	109.4718
C7B—C8B—H3C8B	109.4717	H1C10B—C10B—H2C10B	109.4706
H1C8B—C8B—H2C8B	109.4716	H1C10B—C10B—H3C10B	109.4721
H1C8B—C8B—H3C8B	109.4709	H2C10B—C10B—H3C10B	109.4716
H2C8B—C8B—H3C8B	109.4707	N1A—C1A—C6A	113.4 (2)
Pt1A—N1A—C1A	108.2 (2)	N1A—C1A—C2A	106.4 (2)
Pt1A—N1A—H1N1A	111.6 (19)	N1A—C1A—H1C1A	109.6274
Pt1A—N1A—H2N1A	119.3 (17)	C6A—C1A—C2A	111.4 (2)
C1A—N1A—H1N1A	118 (2)	C6A—C1A—H1C1A	104.3832
C1A—N1A—H2N1A	105 (2)	C2A—C1A—H1C1A	111.7114
H1N1A—N1A—H2N1A	94 (2)	N1B—C1B—C6B	112.8 (3)
Pt1B—N1B—C1B	109.1 (2)	N1B—C1B—C2B	108.2 (2)
Pt1B—N1B—H1N1B	103 (2)	N1B—C1B—H1C1B	108.5941
Pt1B—N1B—H2N1B	113 (4)	C6B—C1B—C2B	110.8 (2)
C1B—N1B—H1N1B	107 (3)	C6B—C1B—H1C1B	105.8029
C1B—N1B—H2N1B	88 (4)	C2B—C1B—H1C1B	110.6521
H1N1B—N1B—H2N1B	134 (4)	N2A—C2A—C3A	113.7 (2)
C1A—C6A—C5A	109.4 (3)	N2A—C2A—C1A	106.6 (2)
C1A—C6A—H1C6A	109.4713	N2A—C2A—H1C2A	109.643
C1A—C6A—H2C6A	109.4717	C3A—C2A—C1A	112.3 (2)
C5A—C6A—H1C6A	109.4708	C3A—C2A—H1C2A	103.5918
C5A—C6A—H2C6A	109.4716	C1A—C2A—H1C2A	111.1002
H1C6A—C6A—H2C6A	109.5667	N2B—C2B—C3B	113.2 (2)
C1B—C6B—C5B	109.4 (3)	N2B—C2B—C1B	107.7 (2)
C1B—C6B—H1C6B	109.4708	N2B—C2B—H1C2B	108.9042
C1B—C6B—H2C6B	109.4718	C3B—C2B—C1B	111.5 (2)
C5B—C6B—H1C6B	109.471	C3B—C2B—H1C2B	104.911
C5B—C6B—H2C6B	109.471	C1B—C2B—H1C2B	110.6513
H1C6B—C6B—H2C6B	109.5564	C6A—C5A—C4A	110.6 (3)
C4A—C3A—C2A	110.3 (3)	C6A—C5A—H1C5A	109.4706
C4A—C3A—H1C3A	109.471	C6A—C5A—H2C5A	109.4709
C4A—C3A—H2C3A	109.4713	C4A—C5A—H1C5A	109.4715
C2A—C3A—H1C3A	109.4707	C4A—C5A—H2C5A	109.4717
C2A—C3A—H2C3A	109.471	H1C5A—C5A—H2C5A	108.3271
H1C3A—C3A—H2C3A	108.6576	C6B—C5B—C4B	111.4 (2)
C4B—C3B—C2B	110.2 (3)	C6B—C5B—H1C5B	109.4712
C4B—C3B—H1C3B	109.4706	C6B—C5B—H2C5B	109.4706
C4B—C3B—H2C3B	109.4705	C4B—C5B—H1C5B	109.4717
C2B—C3B—H1C3B	109.4722	C4B—C5B—H2C5B	109.4713
C2B—C3B—H2C3B	109.4715	H1C5B—C5B—H2C5B	107.4709

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1A—H1N1A···O7B	0.870 (19)	2.030 (17)	2.892 (3)	171 (2)
N1A—H2N1A···O5A	0.87 (2)	2.44 (2)	3.232 (5)	151 (3)
N1A—H2N1A···O6A	0.87 (2)	2.21 (3)	3.013 (5)	154 (3)
N2A—H1N2A···O2A^i	0.870 (14)	2.51 (2)	3.190 (4)	136 (2)
N2A—H1N2A···O3A^i	0.870 (14)	2.207 (11)	3.023 (3)	156 (2)
N2A—H2N2A···O1B^ii	0.87 (2)	2.05 (2)	2.914 (4)	174 (3)
N2A—H2N2A···O3B^ii	0.87 (2)	2.54 (3)	3.064 (3)	119.4 (18)
O7A—H1O7A···O5A^iii	0.80 (3)	2.00 (3)	2.802 (4)	175 (3)
O7A—H2O7A···O4A	0.80 (2)	2.019 (17)	2.757 (5)	153 (3)
O7A—H2O7A···O6A	0.80 (2)	2.57 (3)	3.291 (5)	151 (3)
N1B—H1N1B···O5B	0.87 (3)	2.32 (3)	3.090 (4)	148 (3)
N1B—H1N1B···O6B	0.87 (3)	2.63 (4)	3.207 (4)	125 (3)
N1B—H2N1B···O7A	0.87 (3)	1.95 (4)	2.813 (4)	171 (5)
N2B—H1N2B···O1A^iv	0.87 (3)	2.10 (3)	2.936 (4)	160 (2)
N2B—H1N2B···O3A^iv	0.87 (3)	2.53 (3)	3.238 (3)	140 (3)
N2B—H2N2B···O2B^v	0.87 (3)	2.43 (4)	3.213 (4)	150 (4)
N2B—H2N2B···O3B^v	0.87 (3)	2.21 (2)	3.005 (3)	152 (4)
O7B—H1O7B···O5B^vi	0.80 (3)	2.02 (3)	2.818 (4)	177 (3)
O7B—H2O7B···O4B	0.800 (14)	2.059 (14)	2.846 (5)	168 (3)
O7B—H2O7B···O6B	0.800 (14)	2.85 (3)	3.464 (5)	135 (3)

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