Bis(8-quinolinolato-N,O)platinum(II) and its synthetic intermediate, 8-hydroxyquinolinium dichloro(8-quinolinolato-N,O)platinate(II) tetrahydrate

Bis(8-quinolinolato-N,O)­platinum(II), [Pt(C₉H₆NO)₂], (I), has a centrosymmetric planar structure with trans coordination. The molecules form an inclined π stack, with an interplanar spacing of 3.400 (6) Å. 8-Hydroxy­quinolinium dichloro(8-quinolinolato-N,O)­platinate(II) tetrahydrate, (C₉H₈NO)[PtCl₂(C₉H₆NO)]·4H₂O, (II), is soluble in water and is regarded as the synthetic intermediate of the insoluble neutral compound (I). The uncoordinated 8-hydroxy­quinolinium cations and the monoquinolinolate complexes form an alternating π stack. The origins of fluorescence and phosphorescence in (II) are assigned to the 8-hydroxy­quinolinium cation and the monoquinolinolate–Pt complex, respectively.

S1. Comment

The metal complexes of 8-quinolinol (qH), such as [Alq₃], have attracted much attention recently as luminescent materials. In contrast with [Alq₃], which emits yellow-green fluorescence, bis(8-quinolinolato)platinum(II), [Ptq₂], (I), was reported to emit red phosphorescence with a relatively long lifetime (Ballardini et al., 1986). The origin was deduced to be a ligand-centred excited state, on the basis of the similarity of the emission properties to those of tris(8-quinolinolato)rhodium(III) and -iridium(III) complexes. \sch

In the course of the synthesis of the red crystal of (I), we found a new orange crystal of (II), which showed both yellow fluorescence and red phosphorescence in solution. The emission maxima are 480 and 600 nm in EtOH-MeOH (1:1 v/v) at 77 K, respectively. The phosphorescence spectrum is similar to that for (I) (λ_max = 620 nm).

Compound (II) is soluble in water, and very soluble in organic solvents such as methanol and dimethylsulfoxide, while the neutral compound (I) is much less soluble. However, once compound (II) had dissolved, the red crystal (I) crystallized from the solution. Therefore, (II) can be regarded as the synthetic intermediate of the more stable (I).

X-ray crystallography proved that (II) is an unexpected composite crystal of an uncoordinated 8-hydroxyquinolinium ion and the mono-quinolinolato complex, (qH₂)[PtCl₂q]·4H₂O. In addition, the structure of (I) has also been determined, owing to the successful selection of a single-crystal from mostly twin crystals.

As shown in Fig.1, the molecular structure of (I) is planar and the two 8-quinolinolato ligands are coordinated in a trans geometry. The Pt atom lies on the crystallographic inversion centre. The deviations of atoms from the least squares plane of (I) are within 0.03 Å.

The crystal structure of (I) is isomorphous with the corresponding Pd^II complex (Prout & Wheeler, 1966). The bond lengths and angles for (I) are essentially identical with those for the charge transfer complex [Ptq₂]·TCNQ (TCNQ is 7,7,8,8-tetacyanoquinodimethane; Bergamini et al., 1987). The Pt complexes in (I) are stacked in an inclined fashion, the interplanar spacing of the π–π stack being 3.400 (6) Å. The long Pt—Pt distance of 4.704 (2) Å, which is equal to the cell length of the b axis, suggests no Pt—Pt electronic interaction.

Fig. 2 shows the perspective view of (II). The crystal consists of uncoordinated 8-hydroxyquinolinium cations and mono-quinolinolato Pt complex anions, stacked alternately to form a π stack. The interplanar spacings are found to be typical values for π stacks, 3.44 (1) and 3.47 (1) Å, respectively. The structural features of the integrated stack are similar to those for (ethylenediamine)(α-diimine)platinum(II) complexes and phenanthroline (Kato et al., 2001).

The water molecules in (II) form hydrogen bonds with the Cl^- and quinolinolato ligands in the Pt complex. Differential Fourier synthesis confirmed the exsistence of the 8-hydroxyquinolinium cation in (II), showing the peaks of the H atoms bonded to N and O atoms. The geometry of the 8-hydroxyquinolinium cation is very similar to those of the coordinated quinolinolate ions in (I) and (II).

An additional interesting feature for (II) is the inequality of the coordination angles, in contrast with the symmetrical structure of (II): the Cl2—Pt1—N1 angle is much larger than Cl1—Pt1—O1 (Table 2). This is due to the steric effect of the large Cl atoms and the α-H of the quinolinolato ligand (Cl2···H1 2.70 Å).

On the basis of the structures of (I) and (II), the origin of fluorescence for (II) is assigned to the 8-hydroxyquinolinium cation, while phosphorescence is due to the mono-quinolinolato Pt complex; the latter would have the same origin as that for (I).

S2. Experimental

To an aqueous solution of K₂[PtCl₄] adjusted to ca pH 10, two equimolar amounts of 8-quinolinol (qH) were added and the solution heated for a few minutes. After cooling to room temperature, a dark-orange precipitate was deposited. This was recrystallized from dimethylsulfoxide (DMSO) to give red crystals of (I). The filtrate of the reaction solution was allowed to stand for several days at room temperature to give orange plate crystals of (II). Spectroscopic analysis: ¹H NMR (DMSO-d₆, δ, p.p.m.): for (I): 7.00 (d, 7H), 7.12 (d, 5H), 7.48 (t, 6H), 7.71 (dd, 3H), 8.65 (d, 4H), 8.80 (d, 2H); for (II): 7.01 (d, 7H^c), 7.17 (d, 5H^c), 7.48 (t, 6H^c), 7.71 (dd, 3H^c), 8.67 (d, 4H^c), 9.38 (d, 2H^c), 7.30 (d, 7H^u), 7.57 (m, 5H and 6H^u), 7.79 (dd, 3H^u), 8.71 (d, 4H^u), 8.95 (d, 2H^u), 10.92 (br, –OH^u), where u and c denote the 8-hydroxyquinolinium ion and the coordinated 8-quinolinolate ion, respectively; ESI-MS(-) for (II): 410 ([M]^-), 821 ([2M+H]^-), 843 ([2M+Na]^-).

S3. Refinement

The H atoms of the water molecules for (II) were not included because their positions could not be determined precisely. Other H atoms were treated as riding, with C—H = 0.96–0.98 Å in (I), and C—H = 0.94–0.96, O—H = 1.11 and N—H = 0.88 Å in (II); in both compounds, U_iso(H) = U_eq(C). Are these the correct constraints?

Computing details

For both compounds, data collection: Rigaku/AFC Diffractometer Control Software (Rigaku, 1995); cell refinement: Rigaku/AFC Diffractometer Control Software; data reduction: TEXSAN (Molecular Structure Corporation, 2000); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: TEXSAN.

Figures

	Fig. 1. The molecular structure of (I) showing the atom-numbering scheme and with displacement ellipsoids plotted at the 50% probability level. H atoms are shown as small spheres of arbitary radii.
	Fig. 2. A perspective view of (II) showing the atom-numbering scheme and with displacement ellipsoids plotted at the 50% probability level. H atoms are shown as small spheres of arbitary radii. The hydrate water molecules have been omitted for clarity.

(I)

Crystal data

[Pt(C9H6NO)2]	F(000) = 456.00
Mr = 483.39	Dx = 2.283 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.7107 Å
a = 11.349 (2) Å	Cell parameters from 25 reflections
b = 4.704 (2) Å	θ = 14.6–15.0°
c = 13.731 (1) Å	µ = 9.95 mm^−1
β = 106.43 (1)°	T = 294 K
V = 703.0 (3) Å^3	Plate, orange
Z = 2	0.21 × 0.10 × 0.02 mm

Data collection

Rigaku AFC-7R diffractometer	Rint = 0.015
ω/2θ scans	θmax = 27.5°, θmin = 2.1°
Absorption correction: analytical (de Meulenaer & Tompa, 1965)	h = 0→14
Tmin = 0.397, Tmax = 0.822	k = −6→0
1685 measured reflections	l = −17→17
1607 independent reflections	3 standard reflections every 150 reflections
1053 reflections with I > 2σ(I)	intensity decay: 1.7%

Refinement

Refinement on F^2	w = 1/[σ^2(Fo^2) + (0.0181P)^2] where P = (Fo^2 + 2Fc^2)/3
R[F^2 > 2σ(F^2)] = 0.018	(Δ/σ)max = 0.005
wR(F^2) = 0.045	Δρmax = 0.83 e Å^−3
S = 0.97	Δρmin = −0.43 e Å^−3
1607 reflections	Extinction correction: SHELXL97 (Sheldrick, 1997), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
107 parameters	Extinction coefficient: 0.0006
H-atom parameters constrained

Special details

Refinement. Refinement using reflections with F² > 0.0 σ(F²). The weighted R-factor (wR) and goodness of fit (S) are based on F². R-factor (gt) are based on F. The threshold expression of F² > 2.0 σ(F²) is used only for calculating R-factor (gt).

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

	x	y	z	Uiso*/Ueq
Pt1	0.0000	0.0000	0.0000	0.02828 (9)
O1	−0.1716 (3)	0.1457 (7)	−0.0629 (2)	0.0351 (7)
N1	−0.0042 (3)	0.2755 (8)	0.1092 (3)	0.0303 (8)
C1	0.0835 (4)	0.338 (1)	0.1928 (3)	0.035 (1)
C2	0.0646 (4)	0.536 (1)	0.2631 (3)	0.043 (1)
C3	−0.0448 (4)	0.672 (1)	0.2469 (3)	0.040 (1)
C4	−0.1410 (4)	0.615 (1)	0.1570 (3)	0.033 (1)
C5	−0.2580 (4)	0.742 (1)	0.1312 (4)	0.041 (1)
C6	−0.3420 (4)	0.668 (1)	0.0424 (4)	0.043 (1)
C7	−0.3170 (4)	0.465 (1)	−0.0246 (4)	0.041 (1)
C8	−0.2039 (4)	0.335 (1)	−0.0036 (3)	0.0316 (10)
C9	−0.1157 (4)	0.4122 (9)	0.0897 (3)	0.0293 (10)
H1	0.1620	0.2457	0.2057	0.0349*
H2	0.1303	0.5832	0.3239	0.0427*
H3	−0.0603	0.8029	0.2965	0.0397*
H4	−0.2772	0.8820	0.1769	0.0412*
H5	−0.4212	0.7566	0.0246	0.0428*
H6	−0.3794	0.4211	−0.0863	0.0408*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Pt1	0.0273 (1)	0.0268 (1)	0.0309 (1)	0.0001 (1)	0.00834 (8)	0.0000 (2)
O1	0.027 (1)	0.037 (2)	0.038 (2)	0.001 (2)	0.002 (1)	−0.003 (2)
N1	0.030 (2)	0.028 (2)	0.033 (2)	0.001 (2)	0.009 (1)	0.003 (2)
C1	0.031 (2)	0.034 (3)	0.039 (2)	0.004 (2)	0.008 (2)	0.002 (2)
C2	0.042 (2)	0.047 (4)	0.037 (2)	−0.007 (3)	0.008 (2)	−0.008 (2)
C3	0.047 (3)	0.037 (3)	0.036 (2)	−0.003 (2)	0.013 (2)	−0.010 (2)
C4	0.038 (2)	0.030 (2)	0.035 (2)	−0.002 (2)	0.016 (2)	0.002 (2)
C5	0.043 (3)	0.040 (3)	0.046 (3)	0.002 (2)	0.022 (2)	−0.001 (2)
C6	0.034 (2)	0.044 (3)	0.051 (3)	0.012 (2)	0.014 (2)	0.006 (3)
C7	0.033 (2)	0.039 (3)	0.046 (2)	−0.003 (2)	0.005 (2)	0.000 (2)
C8	0.031 (2)	0.029 (2)	0.037 (2)	0.000 (2)	0.013 (2)	0.002 (2)
C9	0.035 (2)	0.025 (2)	0.031 (2)	−0.002 (2)	0.014 (2)	0.007 (2)

Geometric parameters (Å, º)

Pt1—O1	2.014 (3)	C3—H3	0.971
Pt1—N1	1.992 (4)	C4—C5	1.408 (6)
O1—C8	1.325 (6)	C4—C9	1.413 (7)
N1—C1	1.322 (5)	C5—C6	1.363 (6)
N1—C9	1.377 (6)	C5—H4	0.977
C1—C2	1.401 (7)	C6—C7	1.407 (8)
C1—H1	0.961	C6—H5	0.959
C2—C3	1.359 (7)	C7—C8	1.379 (6)
C2—H2	0.974	C7—H6	0.961
C3—C4	1.423 (6)	C8—C9	1.432 (5)
Pt1···C9^i	3.435 (4)	O1···C2^iii	3.369 (5)
Pt1···C9^ii	3.435 (4)	O1···C6^i	3.531 (6)
Pt1···C4^i	3.527 (5)	O1···N1^ii	3.537 (5)
Pt1···C4^ii	3.527 (5)	N1···C3^i	3.513 (6)
O1···C1^ii	3.330 (6)	C5···C8^iv	3.496 (7)
O1—Pt1—N1	82.8 (1)	C5—C4—C9	118.2 (4)
O1—Pt1—N1^v	97.2 (1)	C4—C5—C6	119.2 (5)
Pt1—O1—C8	111.5 (2)	C4—C5—H4	119.3
Pt1—N1—C1	128.7 (3)	C6—C5—H4	121.5
Pt1—N1—C9	111.9 (2)	C5—C6—C7	122.6 (4)
C1—N1—C9	119.3 (4)	C5—C6—H5	118.9
N1—C1—C2	121.5 (4)	C7—C6—H5	118.4
N1—C1—H1	119.4	C6—C7—C8	120.8 (4)
C2—C1—H1	119.1	C6—C7—H6	119.2
C1—C2—C3	120.7 (4)	C8—C7—H6	119.9
C1—C2—H2	120.9	O1—C8—C7	125.0 (4)
C3—C2—H2	118.3	O1—C8—C9	118.4 (4)
C2—C3—C4	119.6 (5)	C7—C8—C9	116.6 (4)
C2—C3—H3	121.5	N1—C9—C4	122.2 (3)
C4—C3—H3	118.8	N1—C9—C8	115.3 (4)
C3—C4—C5	125.2 (5)	C4—C9—C8	122.5 (4)
C3—C4—C9	116.6 (4)
Pt1—O1—C8—C7	−177.9 (4)	N1—C1—C2—C3	−0.6 (8)
Pt1—O1—C8—C9	2.2 (5)	N1—C9—C4—C3	0.1 (7)
Pt1—O1^v—C8^v—C7^v	177.9 (4)	N1—C9—C4—C5	−179.4 (4)
Pt1—O1^v—C8^v—C9^v	−2.2 (5)	N1—C9—C8—C7	179.1 (4)
Pt1—N1—C1—C2	−179.0 (4)	C1—N1—C9—C4	−1.2 (7)
Pt1—N1—C9—C4	179.2 (4)	C1—N1—C9—C8	178.8 (4)
Pt1—N1—C9—C8	−0.9 (5)	C1—C2—C3—C4	−0.6 (8)
Pt1—N1^v—C1^v—C2^v	179.0 (4)	C2—C1—N1—C9	1.4 (7)
Pt1—N1^v—C9^v—C4^v	−179.2 (4)	C2—C3—C4—C5	−179.8 (5)
Pt1—N1^v—C9^v—C8^v	0.9 (5)	C2—C3—C4—C9	0.8 (7)
O1—Pt1—N1—C1	−178.1 (4)	C3—C4—C5—C6	−180.0 (5)
O1—Pt1—N1—C9	1.6 (3)	C3—C4—C9—C8	−179.9 (4)
O1—Pt1—N1^v—C1^v	−1.9 (4)	C4—C5—C6—C7	0.7 (8)
O1—Pt1—N1^v—C9^v	178.4 (3)	C4—C9—C8—C7	−0.9 (7)
O1—C8—C7—C6	−178.8 (5)	C5—C4—C9—C8	0.6 (7)
O1—C8—C9—N1	−0.9 (6)	C5—C6—C7—C8	−1.0 (8)
O1—C8—C9—C4	179.0 (4)	C6—C5—C4—C9	−0.5 (7)
N1—Pt1—O1—C8	−2.1 (3)	C6—C7—C8—C9	1.1 (7)
N1—Pt1—O1^v—C8^v	−177.9 (3)	C6—C7—C8—C9	1.1 (7)

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

(II)

Crystal data

(C9H8NO)[PtCl2(C9H6NO)]·4H2O	Z = 2
Mr = 628.38	F(000) = 608.00
Triclinic, P1	Dx = 1.949 Mg m^−3
a = 10.665 (3) Å	Mo Kα radiation, λ = 0.7107 Å
b = 14.492 (3) Å	Cell parameters from 25 reflections
c = 7.266 (2) Å	θ = 14.7–15.0°
α = 100.46 (2)°	µ = 6.81 mm^−1
β = 104.13 (2)°	T = 294 K
γ = 85.93 (2)°	Plate query, orange
V = 1070.5 (5) Å^3	0.28 × 0.08 × 0.06 mm

Data collection

Rigaku AFC-7R diffractometer	Rint = 0.023
ω/2θ scans	θmax = 27.5°, θmin = 2.4°
Absorption correction: ψ scan (North et al., 1968)	h = −13→13
Tmin = 0.426, Tmax = 0.664	k = −18→18
5828 measured reflections	l = −9→1
4929 independent reflections	3 standard reflections every 150 reflections
3788 reflections with I > 2σ(I)	intensity decay: 0.1%

Refinement

Refinement on F^2	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.044	w = 1/[σ^2(Fo^2) + (0.0847P)^2 + 1.3493P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.136	(Δ/σ)max = 0.001
S = 1.03	Δρmax = 3.46 e Å^−3
4929 reflections	Δρmin = −1.51 e Å^−3
262 parameters

Special details

Refinement. Refinement using reflections with F² > 0.0 σ(F²). The weighted R-factor (wR) and goodness of fit (S) are based on F². R-factor (gt) are based on F. The threshold expression of F² > 2.0 σ(F²) is used only for calculating R-factor (gt).

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

	x	y	z	Uiso*/Ueq
Pt1	0.52666 (3)	0.24946 (2)	0.27521 (4)	0.0386 (1)
Cl1	0.7165 (2)	0.3297 (2)	0.3921 (4)	0.0629 (6)
Cl2	0.6358 (2)	0.1146 (2)	0.1755 (4)	0.0577 (6)
O1	0.4252 (6)	0.3650 (4)	0.3587 (9)	0.047 (1)
O2	0.1050 (7)	0.0600 (5)	−0.479 (1)	0.065 (2)
O3	0.5152 (8)	0.4663 (5)	0.744 (1)	0.066 (2)
O4	0.730 (1)	0.3961 (7)	−0.019 (1)	0.097 (3)
O5	0.7586 (9)	0.2051 (6)	−0.105 (1)	0.085 (3)
O6	0.8344 (7)	0.1237 (5)	−0.415 (1)	0.065 (2)
N1	0.3520 (7)	0.1928 (4)	0.1890 (9)	0.038 (1)
N2	0.0555 (8)	0.2348 (5)	−0.314 (1)	0.052 (2)
C1	0.3201 (9)	0.1062 (5)	0.100 (1)	0.048 (2)
C2	0.190 (1)	0.0770 (6)	0.053 (2)	0.057 (2)
C3	0.0957 (10)	0.1375 (7)	0.098 (1)	0.056 (2)
C4	0.1274 (9)	0.2316 (6)	0.191 (1)	0.047 (2)
C5	0.0351 (9)	0.3016 (8)	0.242 (1)	0.057 (2)
C6	0.076 (1)	0.3891 (7)	0.328 (1)	0.059 (2)
C7	0.2062 (10)	0.4138 (7)	0.369 (1)	0.052 (2)
C8	0.2988 (9)	0.3475 (6)	0.323 (1)	0.043 (2)
C9	0.2570 (8)	0.2563 (5)	0.234 (1)	0.038 (2)
C10	0.024 (1)	0.3192 (7)	−0.233 (2)	0.058 (2)
C11	0.119 (1)	0.3866 (7)	−0.154 (2)	0.068 (3)
C12	0.243 (1)	0.3622 (7)	−0.161 (2)	0.057 (2)
C13	0.2797 (10)	0.2726 (6)	−0.244 (1)	0.048 (2)
C14	0.406 (1)	0.2429 (9)	−0.254 (2)	0.072 (3)
C15	0.4329 (10)	0.1555 (8)	−0.338 (2)	0.058 (2)
C16	0.333 (1)	0.0909 (8)	−0.413 (2)	0.061 (3)
C17	0.207 (1)	0.1156 (7)	−0.408 (1)	0.052 (2)
C18	0.1786 (9)	0.2074 (6)	−0.325 (1)	0.048 (2)
H1	0.3857	0.0629	0.0680	0.0476*
H2	0.1701	0.0148	−0.0117	0.0565*
H3	0.0091	0.1178	0.0694	0.0559*
H4	−0.0534	0.2873	0.2169	0.0566*
H5	0.0150	0.4359	0.3608	0.0590*
H6	0.2312	0.4763	0.4299	0.0523*
H7	−0.0062	0.1944	−0.3650	0.0520*
H8	−0.0634	0.3361	−0.2316	0.0577*
H9	0.0991	0.4476	−0.0955	0.0678*
H10	0.3081	0.4064	−0.1051	0.0574*
H11	0.4730	0.2873	−0.1994	0.0722*
H12	0.5187	0.1376	−0.3446	0.0577*
H13	0.3533	0.0294	−0.4685	0.0610*
H14	0.1201	−0.0133	−0.5487	0.0646*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Pt1	0.0403 (2)	0.0338 (2)	0.0402 (2)	0.0005 (1)	0.0093 (1)	0.0031 (1)
Cl1	0.044 (1)	0.055 (1)	0.081 (2)	−0.010 (1)	0.009 (1)	−0.005 (1)
Cl2	0.054 (1)	0.043 (1)	0.070 (1)	0.0105 (9)	0.015 (1)	−0.001 (1)
O1	0.050 (4)	0.032 (3)	0.057 (4)	−0.003 (2)	0.017 (3)	−0.003 (2)
O2	0.051 (4)	0.049 (4)	0.090 (5)	−0.013 (3)	0.018 (4)	−0.006 (3)
O3	0.080 (5)	0.060 (4)	0.056 (4)	−0.017 (4)	0.006 (4)	0.011 (3)
O4	0.110 (8)	0.082 (6)	0.089 (7)	−0.021 (6)	−0.004 (6)	0.020 (5)
O5	0.081 (6)	0.081 (6)	0.100 (7)	−0.008 (5)	0.039 (5)	0.007 (5)
O6	0.055 (4)	0.057 (4)	0.079 (5)	0.000 (3)	0.013 (4)	0.006 (4)
N1	0.041 (4)	0.036 (3)	0.036 (3)	−0.002 (3)	0.008 (3)	0.002 (3)
N2	0.054 (4)	0.052 (4)	0.049 (4)	−0.012 (4)	0.009 (4)	0.008 (3)
C1	0.055 (5)	0.030 (4)	0.059 (5)	0.001 (3)	0.021 (4)	0.001 (3)
C2	0.056 (6)	0.037 (4)	0.070 (6)	−0.014 (4)	0.011 (5)	−0.006 (4)
C3	0.051 (5)	0.055 (5)	0.059 (6)	−0.023 (4)	0.011 (4)	−0.002 (4)
C4	0.046 (5)	0.053 (5)	0.044 (4)	0.000 (4)	0.011 (4)	0.012 (4)
C5	0.044 (5)	0.073 (6)	0.052 (5)	0.007 (4)	0.014 (4)	0.009 (5)
C6	0.061 (6)	0.060 (6)	0.053 (5)	0.022 (5)	0.016 (5)	0.009 (4)
C7	0.055 (5)	0.051 (5)	0.045 (5)	0.007 (4)	0.007 (4)	0.001 (4)
C8	0.044 (4)	0.046 (4)	0.039 (4)	0.000 (3)	0.011 (3)	0.006 (3)
C9	0.039 (4)	0.040 (4)	0.035 (4)	−0.002 (3)	0.006 (3)	0.006 (3)
C10	0.062 (6)	0.051 (5)	0.063 (6)	0.007 (4)	0.018 (5)	0.015 (4)
C11	0.110 (10)	0.044 (5)	0.048 (5)	0.005 (5)	0.019 (6)	0.003 (4)
C12	0.067 (7)	0.047 (5)	0.056 (6)	−0.011 (5)	0.007 (5)	0.011 (4)
C13	0.060 (5)	0.052 (5)	0.032 (4)	−0.012 (4)	0.003 (4)	0.011 (3)
C14	0.069 (7)	0.087 (8)	0.063 (7)	−0.031 (7)	0.005 (6)	0.023 (6)
C15	0.043 (5)	0.066 (6)	0.066 (6)	−0.006 (4)	0.011 (4)	0.017 (5)
C16	0.064 (6)	0.057 (6)	0.066 (6)	0.006 (5)	0.022 (5)	0.016 (5)
C17	0.061 (6)	0.049 (5)	0.049 (5)	−0.013 (4)	0.014 (4)	0.009 (4)
C18	0.050 (5)	0.052 (5)	0.045 (4)	−0.003 (4)	0.014 (4)	0.014 (4)

Geometric parameters (Å, º)

Pt1—Cl1	2.304 (3)	C5—H4	0.948
Pt1—Cl2	2.297 (2)	C6—C7	1.40 (2)
Pt1—O1	2.010 (6)	C6—H5	0.948
Pt1—N1	1.999 (7)	C7—C8	1.39 (1)
O1—C8	1.34 (1)	C7—H6	0.959
O2—C17	1.34 (1)	C8—C9	1.41 (1)
O2—H14	1.108	C10—C11	1.41 (2)
N1—C1	1.329 (10)	C10—H8	0.944
N1—C9	1.38 (1)	C11—C12	1.36 (2)
N2—C10	1.32 (1)	C11—H9	0.944
N2—C18	1.36 (1)	C12—C13	1.40 (1)
N2—H7	0.877	C12—H10	0.941
C1—C2	1.42 (1)	C13—C14	1.39 (2)
C1—H1	0.950	C13—C18	1.43 (1)
C2—C3	1.35 (1)	C14—C15	1.35 (2)
C2—H2	0.952	C14—H11	0.960
C3—C4	1.43 (1)	C15—C16	1.41 (2)
C3—H3	0.949	C15—H12	0.945
C4—C5	1.43 (1)	C16—C17	1.37 (2)
C4—C9	1.40 (1)	C16—H13	0.943
C5—C6	1.36 (1)	C17—C18	1.40 (1)
Cl1—Pt1—Cl2	91.55 (9)	C8—C7—H6	119.9
Cl1—Pt1—O1	90.5 (2)	O1—C8—C7	123.7 (8)
Cl1—Pt1—N1	173.3 (2)	O1—C8—C9	118.7 (7)
Cl2—Pt1—O1	178.0 (2)	C7—C8—C9	117.6 (8)
Cl2—Pt1—N1	95.0 (2)	N1—C9—C4	121.6 (7)
O1—Pt1—N1	82.9 (3)	N1—C9—C8	115.7 (7)
Pt1—O1—C8	111.1 (5)	C4—C9—C8	122.7 (8)
C17—O2—H14	119.3	N2—C10—C11	120 (1)
Pt1—N1—C1	129.0 (6)	N2—C10—H8	121.1
Pt1—N1—C9	111.5 (5)	C11—C10—H8	119.2
C1—N1—C9	119.5 (7)	C10—C11—C12	118.7 (9)
C10—N2—C18	123.6 (9)	C10—C11—H9	121.5
C10—N2—H7	118.1	C12—C11—H9	119.8
C18—N2—H7	118.4	C11—C12—C13	122.6 (10)
N1—C1—C2	121.5 (8)	C11—C12—H10	119.0
N1—C1—H1	119.2	C13—C12—H10	118.3
C2—C1—H1	119.3	C12—C13—C14	125.3 (10)
C1—C2—C3	120.2 (8)	C12—C13—C18	116.4 (9)
C1—C2—H2	119.7	C14—C13—C18	118.3 (9)
C3—C2—H2	120.1	C13—C14—C15	121 (1)
C2—C3—C4	119.4 (9)	C13—C14—H11	117.8
C2—C3—H3	120.4	C15—C14—H11	120.4
C4—C3—H3	120.2	C14—C15—C16	119 (1)
C3—C4—C5	124.1 (9)	C14—C15—H12	120.1
C3—C4—C9	117.9 (8)	C16—C15—H12	120.4
C5—C4—C9	118.0 (8)	C15—C16—C17	121.6 (9)
C4—C5—C6	119.0 (9)	C15—C16—H13	118.7
C4—C5—H4	120.6	C17—C16—H13	119.7
C6—C5—H4	120.3	O2—C17—C16	125.9 (9)
C5—C6—C7	122.7 (10)	O2—C17—C18	115.5 (9)
C5—C6—H5	119.3	C16—C17—C18	118.6 (9)
C7—C6—H5	118.0	N2—C18—C13	119.0 (8)
C6—C7—C8	119.9 (8)	N2—C18—C17	120.7 (9)
C6—C7—H6	120.1	C13—C18—C17	120.2 (9)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H7···O2	0.88	2.34	2.674 (9)	103
O2—H14···O2^i	1.11	2.60	2.86 (1)	92
O2—H14···O6^ii	1.11	1.63	2.711 (9)	163
N2—H7···O6^iii	0.88	1.97	2.82 (1)	163

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