Bis(2-amino­pyridine)(2,2'-bi­pyridine)­platinum(II) dinitrate dihydrate

The Pt coordination plane in the title compound, [Pt(C₁₀H₈N₂)(C₅H₆N₂)₂](NO₃)₂·2H₂O, is essentially planar and is nearly coplanar with the 2,2'-bi­pyridine (bpy) ligand. Two 2-amino­pyridine ligands are bound to the Pt atom in a head-to-tail arrangement, and their planes are inclined with respect to the PtN₄ coordination plane by 74.4 (1) and 79.8 (1)°.

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.009 Å
• H-atom completeness 84%
• Disorder in solvent or counterion
• R factor = 0.038
• wR factor = 0.083
• Data-to-parameter ratio = 17.0

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


 Alert Level C:



REFLT_03
         From the CIF: _diffrn_reflns_theta_max           28.22
         From the CIF: _reflns_number_total               5573
         TEST2: Reflns within _diffrn_reflns_theta_max
         Count of symmetry unique reflns         6103
         Completeness (_total/calc)             91.32%
          Alert C: < 95% complete

PLAT_302  Alert C Anion/Solvent Disorder .........................      23.00 Perc.

General Notes



FORMU_01  There is a discrepancy between the atom counts in the
          _chemical_formula_sum and the formula from the _atom_site* data.
          Atom count from _chemical_formula_sum:C20 H24 N8 O8 Pt1
          Atom count from the _atom_site data:  C20 H20 N8 O8 Pt1

ABSTM_02  The ratio of expected to reported Tmax/Tmin(RR') is < 0.50
          Tmin and Tmax reported:      0.147     0.500
          Tmin' and Tmax expected:      0.370     0.578
          RR' =      0.459
          Please check that your absorption correction is appropriate.

CELLZ_01
         From the CIF: _cell_formula_units_Z    4
         From the CIF: _chemical_formula_sum  C20 H24 N8 O8 Pt
         TEST: Compare cell contents of formula and atom_site data

         atom    Z*formula  cif sites diff
         C         80.00     80.00    0.00
         H         96.00     80.00   16.00
         N         32.00     32.00    0.00
         O         32.00     32.00    0.00
         Pt         4.00      4.00    0.00
          Difference between formula and atom_site contents detected.
          WARNING: H atoms missing from atom site list. Is this intentional?

REFLT_03
         From the CIF: _diffrn_reflns_theta_max           28.22
         From the CIF: _reflns_number_total               5573
         From the CIF: _diffrn_reflns_limit_ max hkl    8.   35.   17.
         From the CIF: _diffrn_reflns_limit_ min hkl   -8.  -34.  -12.
         TEST1: Expected hkl limits for theta max
         Calculated maximum hkl    8.   37.   18.
         Calculated minimum hkl   -8.  -37.  -18.
          ALERT: Expected hkl max differ from CIF values


 0 Alert Level A = Potentially serious problem

 0 Alert Level B = Potential problem

 2 Alert Level C = Please check

---

S1. Comment

Multinuclear metal complexes have been considered as important mimics for the catalyst surfaces. It is also known that many important biological processes at the active sites of enzymes often involve various metal complexes having more than two metal centers. In this context, we have been interested in the di- and trinuclear systems involving effective metal–metal interactoins (Sakai et al., 1998), and we recently started exploring the coordination chemistry of platinum and 2-aminopyridine. Up to now, only five crystal structures have been reported for the metal complexes with 2-aminopyridine ligand, in which it serves as either a monodentate ligand (Krizanovic et al., 1993; Xu et al., 2000; Yip et al., 2000) or a bridging ligand (Chakravarty et al., 1984; Kanematsu et al., 1999). The title compound, (I), has been prepared as a precursor to develop new multinuclear systems. The subsequent synthetic studies by use of (I) is now under way. This is the first example of a crystal structure for the platinum complex of 2-aminopyridine.

The Pt coordination plane has a good planarity (Fig. 1 and Table 1), where the four-atom r.m.s. deviation is negligibly small. The Pt atom is shifted out of its coordination plane by 0.012 (2) Å. The bpy ligand has a slightly twisted geometry in which two pyridyl planes are twisted at an angle of 2.0 (1)° to one other. The Pt coordination plane and the bpy plane is nearly coplanar with each other, where their dihedral angle is only 0.80 (1)°. On the other hand, the pyridyl planes of the 2-aminopyridine ligands are largely inclined with respect to the Pt coordination plane, viz. 79.8 (1)° for the plane defined by N3/N4/C11—C15 and 74.4 (1)° for that by N5/N6/C16—C20.

An interesting feature is that one of two nitrates has a strong π-stacking interaction with a part of bpy moiety (Fig. 2), where the plane-to-plane separation is ca 3.28 Å and the two planes are canted at an angle of 6.5 (2)°. The crystal packing is stabilized by weak π–π-stacking interactions (Fig. 3) and also by hydrogen-bonding interactions. The short O···O distances involving the water atoms O7 and O8 are listed in Table 1, and the N—H···O hydrogen-bonding geometry in Table 2.

S2. Experimental

A solution of PtCl₂(bpy) (1.0 mmol, 0.42 g; Morgan & Burstall, 1963), AgNO₃ (2.0 mmol, 0.34 g) and 2-aminopyridine (3.0 mmol, 0.28 g) in water (7 ml) was refluxed for 3 h. The solution was then filtered while it is hot for removal of the AgCl precipitated. The dark purple filtrate was left in air at room temperature overnight. The pale-orange crystals deposited were collected by filtration and air-dried (yield, 35%). The compound was recrystallized from water as follows. The compound was dissolved in water at 333 K (ca 0.1 g in 2 ml H₂O) followed by filtration if necessary. Standing of the filtrate in air at room temperature overnight afforded the final product (I) as pale yellow needles (yield, 10%). Analysis calculated for C₂₀H₂₄N₈O₈Pt: C 34.34, H 3.46, N 16.02%; found: C 34.25, H 3.14, N 16.07%.

S3. Refinement

One of two nitrate anions shows orientational disorder. Around the N8 atom there are two sets of possible positions of (O4A, O5A and O6A) and (O4B, O5B and O6B). It was supposed that these disordered O atoms have the same isotropic displacement parameter. Furthermore, the N—O distances were restrained at 1.22 Å, three O···O distances within each NO₃ group were restrained as equal, and each group was restrained to be planar. The occupation factors of site A and B converged at 56.3 (8) and 43.7 (8)%, respectively. All H atoms, except those of the water molecules, were located at idealized positions as riding atoms (C—H = 0.93 Å for the aromatic rings and N—H = 0.86 Å for the amino groups). Water H atoms were not located. In the final difference Fourier synthesis, four residual peaks in the range 2.13–2.39 e Å⁻³ were observed within 0.88 Å from the Pt atom.

Computing details

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: KENX (Sakai, 2002); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997), TEXSAN (Molecular Structure Corporation, 2001), KENX (Sakai, 2002) and ORTEP (Johnson, 1976).

Figures

	Fig. 1. The structure of (I), showing the atom-labeling scheme. Displacement ellipsoids are shown at the 50% probability level.
	Fig. 2. A view showing a π-stack between the complex cation and a nitrate anion.
	Fig. 3. The crystal packing of (I) viewed along the a (left) and the c axes (right).

Bis(2-aminopyridine)(2,2'-bipyridine)platinum(II) dinitrate dihydrate

Crystal data

[Pt(C10H8N2)(C5H6N2)2](NO3)2·2H2O	? # Insert any comments here.
Mr = 699.56	Dx = 1.871 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 6.7374 (3) Å	Cell parameters from 8388 reflections
b = 27.8864 (13) Å	θ = 2.7–28.0°
c = 13.5619 (6) Å	µ = 5.71 mm^−1
β = 102.876 (1)°	T = 296 K
V = 2483.96 (19) Å^3	Needle, pale yellow
Z = 4	0.17 × 0.12 × 0.10 mm
F(000) = 1368

Data collection

Bruker SMART APEX CCD-detector diffractometer	5573 independent reflections
Radiation source: fine-focus sealed tube	4451 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.098
Detector resolution: 8.366 pixels mm^-1	θmax = 28.2°, θmin = 2.7°
ω scans	h = −8→8
Absorption correction: gaussian (XPREP in SAINT; Bruker, 2001)	k = −34→35
Tmin = 0.147, Tmax = 0.500	l = −12→17
15077 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.083	H-atom parameters constrained
S = 0.95	w = 1/[σ^2(Fo^2) + (0.0327P)^2] where P = (Fo^2 + 2Fc^2)/3
5573 reflections	(Δ/σ)max = 0.002
327 parameters	Δρmax = 2.67 e Å^−3
14 restraints	Δρmin = −0.90 e Å^−3

Special details

Experimental. The first 50 frames were rescanned at the end of data collection to evaluate any possible decay phenomenon. Since it was judged to be negligible, no decay correction was applied to the data.

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.

Mean-plane data from final SHELXL refinement run:-

Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane)

6.5163 (0.0028) x − 0.4491 (0.0367) y + 0.4296 (0.0221) z = 6.4402 (0.0133)

* 0.0004 (0.0020) N1 * −0.0004 (0.0020) N2 * −0.0004 (0.0018) N3 * 0.0004 (0.0018) N5 − 0.0120 (0.0019) Pt1

Rms deviation of fitted atoms = 0.0004

6.5324 (0.0011) x − 0.7080 (0.0415) y + 0.2888 (0.0093) z = 6.3128 (0.0127)

Angle to previous plane (with approximate e.s.d.) = 0.80 (0.09)

* −0.0154 (0.0037) N1 * 0.0057 (0.0036) N2 * −0.0240 (0.0042) C1 * 0.0012 (0.0048) C2 * 0.0300 (0.0047) C3 * 0.0151 (0.0048) C4 * 0.0005 (0.0045) C5 * −0.0064 (0.0042) C6 * −0.0313 (0.0046) C7 * −0.0182 (0.0047) C8 * 0.0172 (0.0046) C9 * 0.0257 (0.0043) C10

Rms deviation of fitted atoms = 0.0189

6.5381 (0.0033) x − 1.1763 (0.0603) y + 0.2102 (0.0269) z = 6.1504 (0.0235)

Angle to previous plane (with approximate e.s.d.) = 1.02 (0.10)

* 0.0051 (0.0033) N1 * −0.0048 (0.0037) C1 * −0.0014 (0.0041) C2 * 0.0070 (0.0041) C3 * −0.0067 (0.0039) C4 * 0.0008 (0.0035) C5

Rms deviation of fitted atoms = 0.0049

6.5144 (0.0035) x − 0.2602 (0.0600) y + 0.4489 (0.0280) z = 6.4940 (0.0200)

Angle to previous plane (with approximate e.s.d.) = 2.14 (0.14)

* −0.0067 (0.0031) N2 * 0.0081 (0.0033) C6 * −0.0030 (0.0038) C7 * −0.0034 (0.0040) C8 * 0.0048 (0.0039) C9 * 0.0002 (0.0036) C10

Rms deviation of fitted atoms = 0.0051

− 2.4963 (0.0096) x + 15.2381 (0.0434) y + 11.0497 (0.0158) z = 7.1776 (0.0170)

Angle to previous plane (with approximate e.s.d.) = 80.10 (0.14)

* −0.0101 (0.0035) N3 * 0.0043 (0.0032) N4 * 0.0006 (0.0046) C11 * −0.0021 (0.0042) C12 * 0.0005 (0.0041) C13 * −0.0014 (0.0043) C14 * 0.0083 (0.0037) C15

Rms deviation of fitted atoms = 0.0053

6.5163 (0.0028) x − 0.4491 (0.0367) y + 0.4296 (0.0221) z = 6.4402 (0.0133)

Angle to previous plane (with approximate e.s.d.) = 79.82 (0.12)

* 0.0004 (0.0020) N1 * −0.0004 (0.0020) N2 * −0.0004 (0.0018) N3 * 0.0004 (0.0018) N5

Rms deviation of fitted atoms = 0.0004

2.6505 (0.0106) x + 23.2789 (0.0294) y − 6.2816 (0.0275) z = 1.2585 (0.0188)

Angle to previous plane (with approximate e.s.d.) = 74.37 (0.12)

* 0.0129 (0.0036) N5 * 0.0023 (0.0035) N6 * −0.0108 (0.0049) C16 * −0.0040 (0.0047) C17 * 0.0096 (0.0046) C18 * −0.0029 (0.0048) C19 * −0.0071 (0.0038) C20

Rms deviation of fitted atoms = 0.0081

− 2.4843 (0.0137) x + 15.2645 (0.0468) y + 11.0469 (0.0158) z = 7.1867 (0.0189)

Angle to previous plane (with approximate e.s.d.) = 88.71 (0.14)

* −0.0079 (0.0033) N3 * 0.0041 (0.0035) C11 * −0.0001 (0.0039) C12 * −0.0002 (0.0041) C13 * −0.0036 (0.0040) C14 * 0.0077 (0.0037) C15

Rms deviation of fitted atoms = 0.0050

6.5163 (0.0028) x − 0.4491 (0.0367) y + 0.4296 (0.0221) z = 6.4402 (0.0133)

Angle to previous plane (with approximate e.s.d.) = 79.93 (0.14)

* 0.0004 (0.0020) N1 * −0.0004 (0.0020) N2 * −0.0004 (0.0018) N3 * 0.0004 (0.0018) N5

Rms deviation of fitted atoms = 0.0004

2.6440 (0.0147) x + 23.2921 (0.0343) y − 6.2782 (0.0275) z = 1.2542 (0.0203)

Angle to previous plane (with approximate e.s.d.) = 74.43 (0.15)

* 0.0140 (0.0034) N5 * −0.0089 (0.0038) C16 * −0.0029 (0.0043) C17 * 0.0092 (0.0046) C18 * −0.0040 (0.0044) C19 * −0.0075 (0.0038) C20

Rms deviation of fitted atoms = 0.0086

6.5324 (0.0011) x − 0.7080 (0.0415) y + 0.2888 (0.0093) z = 6.3128 (0.0127)

Angle to previous plane (with approximate e.s.d.) = 74.60 (0.15)

* −0.0154 (0.0037) N1 * 0.0057 (0.0036) N2 * −0.0240 (0.0042) C1 * 0.0012 (0.0048) C2 * 0.0300 (0.0047) C3 * 0.0151 (0.0048) C4 * 0.0005 (0.0045) C5 * −0.0064 (0.0042) C6 * −0.0313 (0.0046) C7 * −0.0182 (0.0047) C8 * 0.0172 (0.0046) C9 * 0.0257 (0.0043) C10

Rms deviation of fitted atoms = 0.0189

6.5381 (0.0033) x − 1.1763 (0.0603) y + 0.2102 (0.0269) z = 6.1504 (0.0235)

Angle to previous plane (with approximate e.s.d.) = 1.02 (0.10)

* 0.0051 (0.0033) N1 * −0.0048 (0.0037) C1 * −0.0014 (0.0041) C2 * 0.0070 (0.0041) C3 * −0.0067 (0.0039) C4 * 0.0008 (0.0035) C5 − 3.2715 (0.0053) N7 − 3.3935 (0.0057) O1 − 3.1556 (0.0058) O2 − 3.2955 (0.0074) O3

Rms deviation of fitted atoms = 0.0049

6.3595 (0.0074) x − 3.6602 (0.0866) y + 1.1535 (0.0449) z = 2.9771 (0.0331)

Angle to previous plane (with approximate e.s.d.) = 6.51 (0.22)

* 0.0087 (0.0040) N7 * −0.0030 (0.0014) O1 * −0.0029 (0.0013) O2 * −0.0029 (0.0013) O3

Rms deviation of fitted atoms = 0.0050

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)
Pt1	0.95129 (3)	0.136569 (6)	0.676758 (13)	0.03331 (8)
O1	0.4287 (7)	0.17873 (19)	0.7820 (3)	0.0783 (14)
O2	0.4780 (7)	0.2325 (2)	0.6807 (3)	0.0789 (14)
O3	0.4451 (7)	0.1596 (2)	0.6309 (4)	0.0772 (14)
O4A	0.4305 (14)	0.0867 (5)	1.0856 (8)	0.1048 (16)*	0.563 (8)
O4B	0.4755 (19)	0.0602 (5)	1.0534 (10)	0.1048 (16)*	0.437 (8)
O5A	0.6491 (18)	0.0801 (5)	0.9949 (7)	0.1048 (16)*	0.563 (8)
O5B	0.722 (2)	0.0981 (6)	1.0201 (10)	0.1048 (16)*	0.437 (8)
O6A	0.7408 (16)	0.1082 (4)	1.1439 (7)	0.1048 (16)*	0.563 (8)
O6B	0.641 (2)	0.1048 (5)	1.1653 (7)	0.1048 (16)*	0.437 (8)
O7	0.4755 (9)	0.3290 (2)	0.7599 (4)	0.1114 (18)
O8	0.3429 (8)	0.1163 (2)	0.2807 (3)	0.0807 (13)
N1	0.9487 (6)	0.18146 (15)	0.7924 (3)	0.0364 (9)
N2	0.9621 (6)	0.19921 (14)	0.6056 (3)	0.0339 (9)
N3	0.9436 (6)	0.07576 (15)	0.7573 (3)	0.0384 (9)
N4	1.2867 (7)	0.08069 (19)	0.8294 (4)	0.0609 (13)
H4A	1.2930	0.1063	0.7950	0.073*
H4B	1.3945	0.0698	0.8694	0.073*
N5	0.9584 (6)	0.09499 (15)	0.5540 (3)	0.0397 (9)
N6	0.6241 (8)	0.1124 (2)	0.4791 (4)	0.0637 (14)
H6A	0.6126	0.1288	0.5312	0.076*
H6B	0.5220	0.1097	0.4285	0.076*
N7	0.4520 (6)	0.1899 (2)	0.6989 (3)	0.0463 (11)
N8	0.6086 (10)	0.0904 (2)	1.0772 (4)	0.0808 (18)
C1	0.9417 (8)	0.1681 (2)	0.8874 (4)	0.0468 (13)
H1	0.9340	0.1358	0.9028	0.056*
C2	0.9460 (8)	0.2022 (3)	0.9617 (4)	0.0550 (15)
H2	0.9416	0.1927	1.0269	0.066*
C3	0.9565 (9)	0.2495 (2)	0.9400 (4)	0.0592 (16)
H3	0.9612	0.2724	0.9904	0.071*
C4	0.9601 (8)	0.2637 (2)	0.8416 (4)	0.0517 (14)
H4	0.9643	0.2960	0.8249	0.062*
C5	0.9572 (7)	0.2285 (2)	0.7698 (4)	0.0393 (11)
C6	0.9619 (7)	0.23858 (19)	0.6638 (3)	0.0385 (11)
C7	0.9648 (8)	0.2840 (2)	0.6231 (5)	0.0501 (13)
H7	0.9620	0.3109	0.6633	0.060*
C8	0.9717 (9)	0.2892 (2)	0.5249 (5)	0.0556 (15)
H8	0.9740	0.3197	0.4974	0.067*
C9	0.9755 (8)	0.2496 (2)	0.4659 (4)	0.0500 (13)
H9	0.9816	0.2527	0.3984	0.060*
C10	0.9701 (8)	0.2053 (2)	0.5078 (4)	0.0448 (12)
H10	0.9721	0.1783	0.4676	0.054*
C11	1.1119 (9)	0.0581 (2)	0.8206 (4)	0.0467 (13)
C12	1.0964 (10)	0.0156 (2)	0.8755 (4)	0.0578 (16)
H12	1.2117	0.0031	0.9185	0.069*
C13	0.9173 (12)	−0.0066 (2)	0.8660 (5)	0.0671 (19)
H13	0.9087	−0.0344	0.9026	0.081*
C14	0.7427 (10)	0.0118 (2)	0.8009 (4)	0.0618 (17)
H14	0.6177	−0.0035	0.7932	0.074*
C15	0.7614 (9)	0.0531 (2)	0.7491 (4)	0.0528 (14)
H15	0.6460	0.0661	0.7069	0.063*
C16	0.8002 (9)	0.0911 (2)	0.4767 (4)	0.0461 (12)
C17	0.8197 (11)	0.0652 (2)	0.3878 (4)	0.0619 (16)
H17	0.7103	0.0625	0.3325	0.074*
C18	0.9994 (11)	0.0450 (2)	0.3867 (5)	0.0677 (19)
H18	1.0148	0.0286	0.3292	0.081*
C19	1.1630 (11)	0.0481 (2)	0.4690 (5)	0.0636 (17)
H19	1.2865	0.0335	0.4678	0.076*
C20	1.1386 (9)	0.0727 (2)	0.5507 (4)	0.0502 (14)
H20	1.2470	0.0747	0.6066	0.060*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Pt1	0.03748 (11)	0.03486 (11)	0.02778 (11)	0.00070 (8)	0.00767 (7)	−0.00198 (8)
O1	0.099 (4)	0.095 (4)	0.042 (2)	−0.029 (3)	0.017 (2)	−0.004 (2)
O2	0.091 (4)	0.060 (3)	0.083 (4)	−0.013 (3)	0.014 (3)	0.009 (2)
O3	0.071 (3)	0.093 (4)	0.070 (3)	0.001 (3)	0.019 (2)	−0.041 (3)
O7	0.105 (4)	0.097 (5)	0.113 (4)	−0.004 (4)	−0.018 (3)	−0.015 (4)
O8	0.083 (3)	0.089 (4)	0.063 (3)	−0.001 (3)	0.001 (3)	0.002 (3)
N1	0.040 (2)	0.040 (2)	0.029 (2)	−0.0019 (19)	0.0075 (17)	−0.0087 (17)
N2	0.036 (2)	0.036 (2)	0.031 (2)	−0.0004 (17)	0.0086 (16)	0.0004 (17)
N3	0.047 (2)	0.038 (2)	0.032 (2)	−0.0018 (19)	0.0135 (19)	0.0002 (17)
N4	0.048 (3)	0.068 (4)	0.061 (3)	0.003 (3)	0.002 (2)	0.014 (3)
N5	0.053 (2)	0.031 (2)	0.037 (2)	−0.0022 (19)	0.015 (2)	−0.0052 (18)
N6	0.057 (3)	0.085 (4)	0.045 (3)	0.006 (3)	0.003 (2)	−0.017 (3)
N7	0.036 (2)	0.059 (3)	0.044 (3)	−0.005 (2)	0.010 (2)	−0.006 (2)
N8	0.106 (5)	0.048 (3)	0.072 (4)	0.005 (3)	−0.016 (4)	−0.007 (3)
C1	0.051 (3)	0.057 (4)	0.034 (3)	0.001 (3)	0.013 (2)	−0.002 (2)
C2	0.051 (3)	0.083 (5)	0.033 (3)	0.003 (3)	0.011 (2)	−0.009 (3)
C3	0.053 (3)	0.073 (5)	0.051 (4)	0.000 (3)	0.010 (3)	−0.026 (3)
C4	0.049 (3)	0.050 (4)	0.056 (4)	0.007 (3)	0.013 (3)	−0.012 (3)
C5	0.032 (2)	0.048 (3)	0.038 (3)	−0.001 (2)	0.010 (2)	−0.008 (2)
C6	0.030 (2)	0.041 (3)	0.043 (3)	0.000 (2)	0.006 (2)	−0.005 (2)
C7	0.050 (3)	0.038 (3)	0.061 (4)	−0.002 (3)	0.010 (3)	−0.004 (3)
C8	0.060 (3)	0.044 (3)	0.062 (4)	0.000 (3)	0.011 (3)	0.010 (3)
C9	0.054 (3)	0.054 (4)	0.041 (3)	−0.004 (3)	0.009 (3)	0.010 (3)
C10	0.054 (3)	0.046 (3)	0.037 (3)	−0.003 (3)	0.013 (2)	−0.001 (2)
C11	0.064 (3)	0.043 (3)	0.032 (3)	0.006 (3)	0.010 (3)	−0.001 (2)
C12	0.090 (5)	0.047 (3)	0.034 (3)	0.010 (3)	0.008 (3)	0.004 (3)
C13	0.118 (6)	0.045 (3)	0.047 (3)	−0.006 (4)	0.036 (4)	−0.001 (3)
C14	0.081 (4)	0.051 (4)	0.062 (4)	−0.017 (3)	0.035 (4)	−0.004 (3)
C15	0.060 (3)	0.051 (4)	0.051 (3)	−0.005 (3)	0.020 (3)	−0.003 (3)
C16	0.059 (3)	0.046 (3)	0.034 (3)	−0.002 (3)	0.013 (2)	−0.001 (2)
C17	0.090 (5)	0.053 (4)	0.039 (3)	0.000 (3)	0.007 (3)	−0.008 (3)
C18	0.096 (5)	0.059 (4)	0.059 (4)	−0.005 (4)	0.041 (4)	−0.016 (3)
C19	0.077 (4)	0.051 (4)	0.072 (4)	0.006 (3)	0.036 (4)	−0.011 (3)
C20	0.058 (3)	0.044 (3)	0.053 (3)	−0.001 (3)	0.023 (3)	−0.004 (3)

Geometric parameters (Å, º)

Pt1—N2	2.005 (4)	C1—C2	1.380 (8)
Pt1—N1	2.010 (4)	C1—H1	0.9300
Pt1—N3	2.024 (4)	C2—C3	1.358 (9)
Pt1—N5	2.038 (4)	C2—H2	0.9300
O1—N7	1.213 (5)	C3—C4	1.397 (8)
O2—N7	1.232 (7)	C3—H3	0.9300
O2—O7	2.900 (8)	C4—C5	1.379 (7)
O3—N7	1.244 (6)	C4—H4	0.9300
O4A—N8	1.234 (8)	C5—C6	1.472 (6)
O4B—N8	1.218 (8)	C6—C7	1.384 (7)
O5A—N8	1.240 (8)	C7—C8	1.352 (8)
O5B—N8	1.221 (8)	C7—H7	0.9300
O6A—N8	1.225 (8)	C8—C9	1.369 (8)
O6B—N8	1.233 (8)	C8—H8	0.9300
O7—O6A^i	2.633 (11)	C9—C10	1.363 (7)
O7—O8^ii	2.867 (8)	C9—H9	0.9300
O7—O6B^i	2.977 (15)	C10—H10	0.9300
O8—O6B^iii	2.824 (15)	C11—C12	1.415 (8)
O8—O4A^iii	2.955 (12)	C12—C13	1.337 (9)
N1—C5	1.351 (7)	C12—H12	0.9300
N1—C1	1.352 (6)	C13—C14	1.402 (10)
N2—C10	1.350 (6)	C13—H13	0.9300
N2—C6	1.353 (6)	C14—C15	1.368 (8)
N3—C11	1.353 (7)	C14—H14	0.9300
N3—C15	1.363 (7)	C15—H15	0.9300
N4—C11	1.317 (7)	C16—C17	1.437 (7)
N4—H4A	0.8600	C17—C18	1.338 (9)
N4—H4B	0.8600	C17—H17	0.9300
N5—C16	1.322 (7)	C18—C19	1.386 (9)
N5—C20	1.374 (7)	C18—H18	0.9300
N6—C16	1.333 (7)	C19—C20	1.344 (7)
N6—H6A	0.8600	C19—H19	0.9300
N6—H6B	0.8600	C20—H20	0.9300
N2—Pt1—N1	80.82 (16)	C4—C5—C6	123.6 (5)
N2—Pt1—N3	176.21 (15)	N2—C6—C7	120.5 (5)
N1—Pt1—N3	95.44 (16)	N2—C6—C5	114.8 (4)
N2—Pt1—N5	95.31 (15)	C7—C6—C5	124.7 (5)
N1—Pt1—N5	176.07 (16)	C8—C7—C6	119.9 (5)
N3—Pt1—N5	88.42 (16)	C8—C7—H7	120.0
C5—N1—C1	119.7 (4)	C6—C7—H7	120.0
C5—N1—Pt1	114.8 (3)	C7—C8—C9	119.8 (5)
C1—N1—Pt1	125.5 (4)	C7—C8—H8	120.1
C10—N2—C6	118.5 (4)	C9—C8—H8	120.1
C10—N2—Pt1	126.6 (3)	C10—C9—C8	118.9 (5)
C6—N2—Pt1	114.9 (3)	C10—C9—H9	120.5
C11—N3—C15	119.7 (5)	C8—C9—H9	120.5
C11—N3—Pt1	121.9 (4)	N2—C10—C9	122.3 (5)
C15—N3—Pt1	118.4 (4)	N2—C10—H10	118.9
C11—N4—H4A	120.0	C9—C10—H10	118.9
C11—N4—H4B	120.0	N4—C11—N3	119.3 (5)
H4A—N4—H4B	120.0	N4—C11—C12	121.5 (6)
C16—N5—C20	120.0 (4)	N3—C11—C12	119.2 (6)
C16—N5—Pt1	122.1 (3)	C13—C12—C11	120.6 (6)
C20—N5—Pt1	117.8 (4)	C13—C12—H12	119.7
C16—N6—H6A	120.0	C11—C12—H12	119.7
C16—N6—H6B	120.0	C12—C13—C14	120.2 (6)
H6A—N6—H6B	120.0	C12—C13—H13	119.9
O1—N7—O2	119.2 (5)	C14—C13—H13	119.9
O1—N7—O3	121.5 (6)	C15—C14—C13	118.1 (6)
O2—N7—O3	119.3 (5)	C15—C14—H14	120.9
O4B—N8—O5B	118.7 (9)	C13—C14—H14	120.9
O4B—N8—O6B	116.2 (8)	N3—C15—C14	122.1 (6)
O5B—N8—O6B	123.9 (9)	N3—C15—H15	118.9
O6A—N8—O4A	121.8 (8)	C14—C15—H15	118.9
O6A—N8—O5A	119.3 (8)	N5—C16—N6	120.6 (5)
O4A—N8—O5A	118.5 (8)	N5—C16—C17	119.9 (5)
N1—C1—C2	120.4 (6)	N6—C16—C17	119.5 (6)
N1—C1—H1	119.8	C18—C17—C16	118.2 (6)
C2—C1—H1	119.8	C18—C17—H17	120.9
C3—C2—C1	120.3 (5)	C16—C17—H17	120.9
C3—C2—H2	119.8	C17—C18—C19	121.6 (6)
C1—C2—H2	119.8	C17—C18—H18	119.2
C2—C3—C4	119.7 (5)	C19—C18—H18	119.2
C2—C3—H3	120.2	C20—C19—C18	118.3 (6)
C4—C3—H3	120.2	C20—C19—H19	120.9
C5—C4—C3	118.2 (6)	C18—C19—H19	120.9
C5—C4—H4	120.9	C19—C20—N5	122.0 (6)
C3—C4—H4	120.9	C19—C20—H20	119.0
N1—C5—C4	121.7 (5)	N5—C20—H20	119.0
N1—C5—C6	114.7 (4)
C5—N1—C1—C2	−0.9 (8)	C6—N2—C10—C9	−0.8 (7)
N1—C1—C2—C3	0.2 (9)	C8—C9—C10—N2	−0.3 (8)
C1—C2—C3—C4	0.9 (9)	C15—N3—C11—N4	−178.9 (5)
C2—C3—C4—C5	−1.4 (9)	C15—N3—C11—C12	1.5 (7)
C1—N1—C5—C4	0.3 (7)	N4—C11—C12—C13	179.7 (5)
C1—N1—C5—C6	−179.4 (4)	N3—C11—C12—C13	−0.8 (8)
C3—C4—C5—N1	0.8 (8)	C11—C12—C13—C14	0.3 (9)
C3—C4—C5—C6	−179.6 (5)	C12—C13—C14—C15	−0.7 (9)
C10—N2—C6—C7	1.6 (7)	C11—N3—C15—C14	−1.9 (8)
C10—N2—C6—C5	−178.8 (4)	C13—C14—C15—N3	1.5 (8)
N1—C5—C6—N2	−1.6 (6)	C20—N5—C16—N6	179.7 (5)
C4—C5—C6—N2	178.8 (5)	C20—N5—C16—C17	−2.5 (8)
N1—C5—C6—C7	178.1 (5)	N5—C16—C17—C18	0.8 (9)
C4—C5—C6—C7	−1.6 (8)	N6—C16—C17—C18	178.7 (6)
N2—C6—C7—C8	−1.2 (8)	C16—C17—C18—C19	1.0 (10)
C5—C6—C7—C8	179.2 (5)	C17—C18—C19—C20	−1.1 (10)
C6—C7—C8—C9	0.1 (9)	C18—C19—C20—N5	−0.6 (9)
C7—C8—C9—C10	0.6 (9)	C16—N5—C20—C19	2.4 (8)

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

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N6—H6A···O3	0.86	2.13	2.922 (6)	154
N6—H6B···O8	0.86	2.10	2.926 (7)	160
N4—H4A···O1^iv	0.86	2.24	3.013 (7)	150
N4—H4B···O4B^iv	0.86	2.45	3.074 (14)	130
N4—H4B···O5A^iv	0.86	2.15	2.926 (13)	150

Symmetry code: (iv) x+1, y, z.