cis- and trans-Dichloro(3,6-dihydro-1,2-oxazine-N)(dimethyl sulfoxide-S)-platinum(II)

Both the cis, (I), and trans, (II), isomers of the title complex, [PtCl₂(C₄H₇NO)(C₂H₆OS)], possess relatively undistorted square-planar geometries about the Pt atoms. For (I), cis L-Pt-L angles are in the range 88.8 (2)-91.08 (8)°, while trans angles are 178.61 (8) and 179.4 (2)°. For (II), cis L-Pt-L 86.1 (3)-93.7 (1)°, and trans L-Pt-L 175.5 (1) and 179.1 (3)°. The di­methyl sulfoxide (dmso) ligand adopts a normal pyramidal geometry in both complexes. In (I), the S=O bond essentially eclipses the adjacent Pt-N bond, while the oxazine ligand in (I) is twisted so as to avoid steric interactions with the adjacent chloride ligand. By contrast, the dmso ligand in (II) is rotated such that the S=O bond is approximately perpendicular to the square plane, while the oxazine ligand is once again twisted out of the plane by a similar amount as in (I). These are the first structural examples of square-planar platinum(II) complexes containing a 1,2-oxazine ligand.

S1. Comment

Since the discovery of the antitumor activity of cis-diamminedichloroplatinum(II) (cisplatin), a large number of square-planar platinum complexes have been studied as potential chemotherapeutic drugs which might maintain the efficacy of cisplatin without the undesirable side effects (Lippard, 1982; Rosenberg, 1985). Typically, these complexes consist of two inert cis ammine ligands and two labile cis ligands which act as leaving groups in the body, thus allowing the platinum to coordinate to the DNA of cancer cells. One complex which has achieved widespread use as an alternative to cisplatin is cis-diammine(1,1-cyclobutanedicarboxylato)platinum(II) (carboplatin). The use of 1,2-oxazines as nitrogen ligands could lead to novel compounds with increased antitumor activity or decreased toxicity due to the demonstrated biological activity of the oxazine and the easily cleaved N—O bond in the oxazine ring. Compounds (I) and (II) were obtained from an unsuccessful effort to synthesize cis-bis(3,6-dihydro-1,2-oxazine)1,1-cyclobutanedicarboxylatoplatinum(II) through an intermediate DMSO complex. They represent new members of a modest family of square planar [PtCl₂(DMSO)(amine)] complexes whose structural features they share.

The cis isomer (I) of dichloro(3,6-dihydro-1,2-oxazine-N)(dimethyl sulfoxide-S)platinum(II) is shown in Fig. 1. The Pt coordination geometry (Table 1) is quite regular, with all angles within 1.4° of their ideal values. The mean devation from the PtCl₂SN least squares plane is 0.011 (3) Å. The Pt—Cl distance opposite the DMSO ligand is 0.015 (3) Å longer than that opposite the oxazine ligand. This is consistent with what is observed in most of the reported cis-[PtCl₂(DMSO)(amine)] complexes (Melanson & Rochon, 1977; Belsky et al., 1990, 1991; Rochon et al., 1990, 1994; Neuse et al., 1995; Caldwell et al., 1995; Cornia et al., 1997). The Pt—S and Pt—N distances are also within the reported ranges [2.184 (3)–2.225 (2) and 1.950 (6)–2.06 (1) Å, respectively], including those of two platinum 1,3-oxazine complexes (Albinati et al., 1989; Michelin et al., 1994). The pyramidal DMSO ligand is positioned so that the S═O bond is nearly coplanar with the square plane [torsion angle O2–S–Pt–N −4.6 (3)°], while the S—C bonds are staggered between the Pt—Cl1 bond [torsion angle Cl1—Pt—S—C5 − 62.6 (4)°]. This arrangement is also observed when the amine ligand is 2-picoline (Melanson & Rochon, 1977), pyridine (Belsky et al., 1991), cylopentylamine (Caldwell et al., 1995), tert-butylamine (Neuse et al., 1995), and thiazole (Cornia et al., 1997). For acetonitrile, two structures have been reported, one with S═ O eclipsing Pt—N (Rochon et al., 1990) and one with an S—C bond approximately aligned with Pt—N (Belsky et al., 1990). The latter conformation is also found in the propionitrile complex (Rochon et al., 1994). The S═O bond at 1.489 (5) Å is significantly shorter than that in the free molecule at 278 K [1.531 (5) Å] (Davies, 1981), but is at the high end of the range found in similar Pt complexes [1.44 (3)–1.48 (1) Å]. As in the free DMSO, the O—S—C angles are larger than the C—S—C angle, though the difference is smaller in the complex. The oxazine molecule shows bond distances and angles consistent with those found in non-coordinated 1,2-oxazine derivatives (Riddell et al., 1974; Holzapfel et al., 1987). It is positioned so that the N—O1 and N—C4 bonds are staggered about Cl2 [torsion angles Cl2—Pt—N—C4 62.2 (5) and Cl2–Pt–N–O1 − 63.3 (4) Å].

The trans isomer (II) is shown in Fig. 2. The Pt coordination geometry (Table 2) is slightly less regular than that of the cis isomer in that the Cl—Pt—Cl angle is closed 4.5° from ideal, causing a similar ca 3–4° distortion in the Cl2—Pt—S and Cl2—Pt—N angles. The mean deviation from the PtCl₂SN plane is 0.021 (4) Å, with the two chloride ligands displaced 0.041 (4) and 0.035 (4) Å to the same side of the plane. As is the case in trans-[PtCl₂(DMSO)(amine)] complexes (Melanson & Rochon, 1978; Caruso et al., 1980; Viossat et al., 1991; Lovqvist & Oskarsson, 1992; Cornia et al., 1997), the Pt—Cl bond distances are closer to one another than in (I) and within experimental error. The Pt—S distance [2.230 (3) Å] is nearly 0.01 Å longer than the longest reported distance for this type of complex, while the Pt—N distance [2.067 (9) Å] is to the high end of the reported range [2.03 (1)–2.08 (2) Å] as is the S—O bond length. The DMSO ligand is positioned quite differently from that in (I). The S═O bond is almost perpendicular to the square plane [torsion angle Cl2–Pt–S–O2 100.5 (4)°], while the S—C5 bond is the closest to being in the plane [torsion angle Cl2—Pt—S—C5 − 24.6 (6)°]. A similar arrangement is found in trans-[PtCl₂(DMSO)(NH₃)] (Viossat et al., 1991), while other skewed orientations with the S═O group directed away from the square plane are found in the pyridine (Caruso et al., 1980), piperidine (Lovqvist & Oskarsson, 1992) and thiazole (Cornia et al., 1997) complexes. Only the cytidine complex (Melanson & Rochon, 1978) differs in having the S═O bond eclipsing an adjacent ligand as in (I). The bond distances and angles within the oxazine ligand do not differ significantly from those in (I). The conformation of the ring is also essentially the same [torsion angles for (I) and (II), respectively: N—C4—C3—C2 12 (1), 14 (2)°; N—O1—C1—C2 − 49.6 (8), −48 (1)°]. The ring is positioned similarly to that in the cis isomer with the N—O1 and N—C4 bonds rotated away from the adjacent Cl ligands [torsion angles Cl1—Pt—N—O1 − 55.6 (6) and Cl1—Pt—N—C4 67.9 (9)°].

S2. Experimental

For (I), a solution of cis-bis(dimethyl sulfoxide)(1,1-cyclobutanedicarboxylato)platinum(II) (0.502 g, 0.95 mmol) and 3,6-dihydro-1,2-oxazinium chloride (0.239 g, 1.95 mmol) in water (30 ml) was stirred at room temperature for 0.5 h. The yellow crystals which formed were collected by filtration, washed with several portions of distilled water, and dried at 323 K and 2666.45 Pa to provide cis-dichloro(3,6-dihydro-1,2-oxazine-N)(dimethyl sulfoxide-S)platinum(II) (0.269 g). For (II), to a stirred solution of cis-bis(dimethyl sulfoxide)(1,1-cyclobutanedicarboxylato)platinum(II) (0.314 g, 0.60 mmol) in water (20 ml) was added, dropwise, a solution of 3,6-dihydro-1,2-oxazine (0.149 g, 1.23 mmol) in water (5.0 ml) (pH adjusted to 4.0 with aqueous hydrochloric acid solution). The resulting solution was stirred at 328 K for 2 h and then allowed to stand at room temperature for 2 d. The volume of solution was reduced by rotary evaporation of the solvent at reduced pressure. The solid product was collected, washed repeatedly with distilled water, and dried at 323 K and 2666.45 Pa to provide trans-dichloro(3,6-dihydro-1,2-oxazine-N)(dimethyl sulfoxide-S)platinum(II) (0.167 g).

S3. Refinement

The minimum and maximum points on the final difference electron-density map were 1.03 and 1.27 Å, respectively, from the Pt atom. The minimum and maximum peaks in the final difference electron-density map were 1.02 Å from Pt and 1.63 Å from H9, respectively.

Computing details

For both compounds, data collection: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1988); cell refinement: MSC/AFC Diffractometer Control Software; data reduction: TEXSAN (Molecular Structure Corporation, 1991); program(s) used to solve structure: MITHRIL (Gilmore, 1983); program(s) used to refine structure: TEXSAN; molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: TEXSAN.

Figures

	Fig. 1. An ORTEPII diagram (Johnson, 1976) showing the molecular structure and atom-labelling scheme of (I). The displacement ellipsoids of the non-H atoms are shown at the 50% probability level.
	Fig. 2. An ORTEPII diagram (Johnson, 1976) showing the molecular structure and atom-labelling scheme of (II). The displacement ellipsoids of the non-H atoms are shown at the 50% probability level.

(I)

Crystal data

[PtCl2(C4H7NO)(C2H6OS)]	Z = 2
Mr = 429.23	F(000) = 400
Triclinic, P1	Dx = 2.403 Mg m^−3
a = 8.177 (4) Å	Mo Kα radiation, λ = 0.7107 Å
b = 8.517 (4) Å	Cell parameters from 22 reflections
c = 10.297 (4) Å	θ = 20.6–22.4°
α = 105.84 (3)°	µ = 12.6 mm^−1
β = 104.42 (3)°	T = 296 K
γ = 111.16 (3)°	Slab, pale yellow
V = 593.2 (5) Å^3	0.25 × 0.12 × 0.10 mm

Data collection

Rigaku AFC6S diffractometer	1820 reflections with I > 3σ(I)
Radiation source: X-ray tube	Rint = 0.013
Graphite monochromator	θmax = 25.0°
ω–2θ scans	h = 0→9
Absorption correction: ψ scan (North et al., 1968)	k = −10→9
Tmin = 0.190, Tmax = 0.284	l = −12→11
2249 measured reflections	3 standard reflections every 150 reflections
2089 independent reflections	intensity decay: 2.3%

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	0 constraints
R[F^2 > 2σ(F^2)] = 0.026	H-atom parameters not refined
wR(F^2) = 0.059	Weighting scheme based on measured s.u.'s w = 4Fo^2/σ^2(Fo^2)
S = 2.23	(Δ/σ)max = 0.001
2087 reflections	Δρmax = 0.73 e Å^−3
118 parameters	Δρmin = −1.75 e Å^−3

Special details

Refinement. The minimum and maximum points on the final difference electron density map were 1.03 and 1.27 Å, respectively, from the Pt atom.

H atoms were located on difference electron-density maps and their positions idealized (X—H 0.95 Å) with B_iso values set at 1.2 times B_eq of the attached atom at the time of their inclusion.

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

	x	y	z	Uiso*/Ueq
Pt	0.24440 (5)	0.21118 (4)	0.24855 (3)	0.03340 (9)
Cl1	0.2700 (4)	0.0318 (3)	0.3774 (3)	0.0608 (8)
Cl2	0.3838 (3)	0.0909 (3)	0.1045 (3)	0.0513 (7)
S	0.1078 (3)	0.3257 (3)	0.3807 (2)	0.0384 (6)
O1	0.4130 (7)	0.5031 (7)	0.1580 (6)	0.049 (2)
O2	0.0728 (8)	0.4734 (8)	0.3483 (6)	0.049 (2)
N	0.2241 (9)	0.3738 (8)	0.1355 (7)	0.037 (2)
C1	0.405 (1)	0.651 (1)	0.1163 (10)	0.052 (3)
C2	0.255 (1)	0.580 (1)	−0.0310 (10)	0.048 (3)
C3	0.122 (1)	0.408 (1)	−0.0957 (9)	0.045 (3)
C4	0.104 (1)	0.279 (1)	−0.0232 (8)	0.042 (2)
C5	−0.112 (1)	0.153 (1)	0.358 (1)	0.060 (3)
C6	0.244 (1)	0.412 (1)	0.5716 (9)	0.061 (3)
H1	0.1700	0.4447	0.1787	0.0448
H2	0.3788	0.7272	0.1861	0.0627
H3	0.5246	0.7223	0.1153	0.0627
H4	0.2550	0.6598	−0.0795	0.0576
H5	0.0334	0.3650	−0.1927	0.0543
H6	−0.0247	0.2163	−0.0357	0.0509
H7	0.1424	0.1921	−0.0674	0.0509
H8	−0.1603	0.2040	0.4242	0.0716
H9	−0.0940	0.0561	0.3769	0.0716
H10	−0.2010	0.1057	0.2603	0.0716
H11	0.3500	0.5275	0.6014	0.0735
H12	0.2880	0.3277	0.5904	0.0735
H13	0.1671	0.4256	0.6249	0.0735

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Pt	0.0378 (2)	0.0339 (2)	0.0299 (2)	0.0156 (1)	0.0139 (1)	0.0153 (1)
Cl1	0.091 (2)	0.061 (1)	0.055 (1)	0.045 (1)	0.032 (1)	0.039 (1)
Cl2	0.060 (1)	0.049 (1)	0.064 (2)	0.032 (1)	0.039 (1)	0.027 (1)
S	0.041 (1)	0.050 (1)	0.027 (1)	0.021 (1)	0.0143 (10)	0.0187 (10)
O1	0.035 (3)	0.047 (3)	0.050 (4)	0.007 (3)	0.007 (3)	0.025 (3)
O2	0.071 (4)	0.062 (4)	0.046 (4)	0.046 (3)	0.033 (3)	0.036 (3)
N	0.042 (4)	0.044 (4)	0.031 (4)	0.020 (3)	0.017 (3)	0.020 (3)
C1	0.052 (6)	0.045 (5)	0.058 (6)	0.015 (4)	0.018 (5)	0.030 (5)
C2	0.052 (6)	0.056 (6)	0.051 (6)	0.025 (5)	0.028 (5)	0.036 (5)
C3	0.056 (6)	0.061 (6)	0.033 (5)	0.031 (5)	0.023 (4)	0.028 (4)
C4	0.041 (5)	0.040 (5)	0.032 (5)	0.011 (4)	0.007 (4)	0.011 (4)
C5	0.052 (6)	0.065 (6)	0.062 (6)	0.020 (5)	0.029 (5)	0.029 (5)
C6	0.066 (6)	0.087 (7)	0.020 (4)	0.040 (6)	0.009 (4)	0.007 (4)

Geometric parameters (Å, º)

Pt—Cl1	2.310 (2)	N—H1	0.95
Pt—Cl2	2.325 (2)	C1—H2	0.95
Pt—S	2.207 (2)	C1—H3	0.95
Pt—N	2.062 (6)	C2—H4	0.95
S—O2	1.489 (5)	C3—H5	0.95
S—C5	1.776 (9)	C4—H6	0.95
S—C6	1.783 (8)	C4—H7	0.95
O1—N	1.452 (7)	C5—H8	0.95
O1—C1	1.458 (9)	C5—H9	0.95
N—C4	1.480 (9)	C5—H10	0.95
C1—C2	1.49 (1)	C6—H11	0.95
C2—C3	1.32 (1)	C6—H12	0.95
C3—C4	1.47 (1)	C6—H13	0.95
Cl1—Pt—Cl2	90.07 (8)	C2—C1—H2	109
Cl1—Pt—S	91.08 (8)	C2—C1—H3	109
Cl1—Pt—N	179.4 (2)	H2—C1—H3	109
Cl2—Pt—S	178.61 (8)	C1—C2—H4	119
Cl2—Pt—N	90.1 (2)	C3—C2—H4	119
S—Pt—N	88.8 (2)	C2—C3—H5	119
Pt—S—O2	113.8 (2)	C4—C3—H5	119
Pt—S—C5	111.7 (3)	N—C4—H6	109
Pt—S—C6	111.2 (3)	N—C4—H7	109
O2—S—C5	107.9 (4)	C3—C4—H6	109
O2—S—C6	108.9 (4)	C3—C4—H7	109
C5—S—C6	102.7 (4)	H6—C4—H7	109
N—O1—C1	110.2 (5)	S—C5—H8	109
Pt—N—O1	109.8 (4)	S—C5—H9	109
Pt—N—C4	117.1 (5)	S—C5—H10	109
O1—N—C4	109.4 (5)	H8—C5—H9	109
O1—C1—C2	111.6 (7)	H8—C5—H10	109
C1—C2—C3	121.5 (8)	H9—C5—H10	109
C2—C3—C4	122.3 (8)	S—C6—H11	110
N—C4—C3	112.1 (6)	S—C6—H12	110
Pt—N—H1	107	S—C6—H13	110
O1—N—H1	107	H11—C6—H12	109
C4—N—H1	107	H11—C6—H13	109
O1—C1—H2	109	H12—C6—H13	109
O1—C1—H3	109
Pt—N—O1—C1	−163.4 (5)	O1—N—C4—C3	−46.4 (8)
Pt—N—C4—C3	−172.1 (5)	O1—C1—C2—C3	15 (1)
Cl1—Pt—S—O2	174.8 (3)	O2—S—Pt—N	−4.6 (3)
Cl1—Pt—S—C5	−62.6 (4)	N—Pt—S—C5	118.0 (4)
Cl1—Pt—S—C6	51.4 (4)	N—Pt—S—C6	−128.0 (4)
Cl2—Pt—N—O1	−63.3 (4)	N—O1—C1—C2	−49.6 (8)
Cl2—Pt—N—C4	62.2 (5)	N—C4—C3—C2	12 (1)
S—Pt—N—O1	117.5 (4)	C1—O1—N—C4	66.8 (7)
S—Pt—N—C4	−117.0 (5)	C1—C2—C3—C4	4 (1)

(II)

Crystal data

[PtCl2(C4H7NO)(C2H6OS)]	Dx = 2.442 Mg m^−3
Mr = 429.23	Mo Kα radiation, λ = 0.7107 Å
Orthorhombic, Pbca	Cell parameters from 20 reflections
a = 16.532 (3) Å	θ = 15.5–20.3°
b = 13.868 (2) Å	µ = 12.8 mm^−1
c = 10.182 (4) Å	T = 296 K
V = 2334 (1) Å^3	Hexagonal plate, pale yellow
Z = 8	0.30 × 0.10 × 0.03 mm
F(000) = 1600

Data collection

Rigaku AFC6S diffractometer	1277 reflections with I > 3σ(I)
Radiation source: X-ray tube	Rint = 0.00
Graphite monochromator	θmax = 25.0°
ω–2θ scans	h = 0→19
Absorption correction: ψ scan (North et al., 1968)	k = 0→16
Tmin = 0.242, Tmax = 0.681	l = −12→0
2053 measured reflections	3 standard reflections every 150 reflections
2053 independent reflections	intensity decay: −0.1%

Refinement

Refinement on F^2	0 constraints
Least-squares matrix: full	H-atom parameters not refined
R[F^2 > 2σ(F^2)] = 0.032	Weighting scheme based on measured s.u.'s w = 4Fo^2/σ^2(Fo^2)
wR(F^2) = 0.074	(Δ/σ)max = 0.001
S = 1.71	Δρmax = 1.95 e Å^−3
2049 reflections	Δρmin = −2.09 e Å^−3
119 parameters	Extinction correction: Zachariasen (1968) type 2 Gaussian isotropic
0 restraints	Extinction coefficient: 0.00000010 (5)

Special details

Refinement. The minimum and maximum peaks in the final difference map were 1.02 Å from Pt and 1.63 Å from H9, respectively.

H atoms were located on difference electron-density maps and their positions idealized (X—H 0.95 Å) with B_iso values set at 1.2 times B_eq of the attached atom at the time of their inclusion.

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

	x	y	z	Uiso*/Ueq
Pt	0.04257 (3)	0.07117 (3)	0.72831 (4)	0.0280 (1)
Cl1	0.1433 (2)	0.1845 (2)	0.7486 (4)	0.0478 (10)
Cl2	−0.0533 (2)	−0.0483 (2)	0.7217 (4)	0.0457 (9)
S	−0.0391 (2)	0.1812 (2)	0.6393 (3)	0.0358 (9)
O1	0.1921 (5)	−0.0372 (5)	0.7407 (10)	0.040 (2)
O2	−0.0767 (5)	0.2498 (5)	0.7326 (9)	0.046 (2)
N	0.1173 (6)	−0.0308 (6)	0.8133 (10)	0.035 (3)
C1	0.2384 (8)	−0.1211 (8)	0.779 (1)	0.046 (4)
C2	0.2459 (9)	−0.1305 (9)	0.922 (2)	0.053 (5)
C3	0.2007 (9)	−0.081 (1)	1.006 (1)	0.056 (5)
C4	0.1360 (10)	−0.0145 (9)	0.954 (1)	0.047 (4)
C5	−0.118 (1)	0.1284 (9)	0.542 (1)	0.061 (5)
C6	0.0137 (9)	0.249 (1)	0.518 (2)	0.064 (5)
H1	0.0909	−0.0914	0.8066	0.0419
H2	0.2911	−0.1161	0.7418	0.0551
H3	0.2124	−0.1770	0.7452	0.0551
H4	0.2850	−0.1740	0.9555	0.0630
H5	0.2091	−0.0875	1.0976	0.0669
H6	0.1537	0.0502	0.9643	0.0572
H7	0.0880	−0.0243	1.0034	0.0572
H8	−0.0952	0.0785	0.4895	0.0728
H9	−0.1578	0.1025	0.5982	0.0728
H10	−0.1406	0.1764	0.4873	0.0728
H11	−0.0242	0.2816	0.4636	0.0766
H12	0.0480	0.2944	0.5593	0.0766
H13	0.0453	0.2063	0.4655	0.0766

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Pt	0.0253 (3)	0.0279 (2)	0.0308 (3)	0.0011 (2)	0.0000 (3)	−0.0041 (2)
Cl1	0.035 (2)	0.035 (1)	0.072 (3)	−0.009 (1)	−0.004 (2)	−0.003 (2)
Cl2	0.030 (2)	0.038 (2)	0.069 (2)	−0.005 (1)	−0.003 (2)	0.001 (2)
S	0.038 (2)	0.033 (1)	0.036 (2)	0.006 (2)	−0.006 (2)	−0.006 (1)
O1	0.029 (5)	0.036 (4)	0.053 (6)	0.008 (4)	0.004 (5)	0.006 (5)
O2	0.054 (5)	0.046 (4)	0.038 (5)	0.013 (4)	−0.016 (5)	−0.007 (4)
N	0.023 (6)	0.034 (5)	0.047 (7)	0.002 (5)	−0.006 (6)	0.000 (5)
C1	0.025 (7)	0.041 (7)	0.07 (1)	0.008 (6)	0.002 (9)	0.006 (8)
C2	0.042 (10)	0.046 (9)	0.07 (1)	0.001 (8)	−0.012 (10)	0.000 (8)
C3	0.06 (1)	0.063 (9)	0.049 (9)	−0.011 (9)	−0.019 (8)	0.004 (9)
C4	0.06 (1)	0.059 (8)	0.023 (8)	0.001 (8)	0.004 (8)	−0.003 (7)
C5	0.06 (1)	0.051 (8)	0.07 (1)	−0.001 (8)	−0.037 (10)	0.006 (8)
C6	0.08 (1)	0.055 (7)	0.052 (9)	0.00 (1)	0.00 (1)	0.017 (7)

Geometric parameters (Å, º)

Pt—Cl1	2.300 (3)	N—H1	0.95
Pt—Cl2	2.294 (3)	C1—H2	0.95
Pt—S	2.230 (3)	C1—H3	0.95
Pt—N	2.067 (9)	C2—H4	0.95
S—O2	1.480 (8)	C3—H5	0.95
S—C5	1.79 (1)	C4—H6	0.95
S—C6	1.78 (1)	C4—H7	0.95
O1—N	1.44 (1)	C5—H8	0.95
O1—C1	1.44 (1)	C5—H9	0.95
N—C4	1.48 (1)	C5—H10	0.95
C1—C2	1.47 (2)	C6—H11	0.95
C2—C3	1.33 (2)	C6—H12	0.95
C3—C4	1.51 (2)	C6—H13	0.95
Cl1—Pt—Cl2	175.5 (1)	C2—C1—H2	109
Cl1—Pt—S	90.4 (1)	C2—C1—H3	109
Cl1—Pt—N	89.8 (3)	H2—C1—H3	109
Cl2—Pt—S	93.7 (1)	C1—C2—H4	118
Cl2—Pt—N	86.1 (3)	C3—C2—H4	118
S—Pt—N	179.1 (3)	C2—C3—H5	120
Pt—S—O2	115.7 (4)	C4—C3—H5	120
Pt—S—C5	112.5 (4)	N—C4—H6	108
Pt—S—C6	110.2 (5)	N—C4—H7	108
O2—S—C5	108.2 (6)	C3—C4—H6	109
O2—S—C6	108.3 (6)	C3—C4—H7	109
C5—S—C6	100.8 (7)	H6—C4—H7	109
N—O1—C1	111.5 (9)	S—C5—H8	109
Pt—N—O1	109.9 (6)	S—C5—H9	109
Pt—N—C4	115.2 (8)	S—C5—H10	109
O1—N—C4	109 (1)	H8—C5—H9	110
O1—C1—C2	112 (1)	H8—C5—H10	109
C1—C2—C3	123 (1)	H9—C5—H10	110
C2—C3—C4	119 (1)	S—C6—H11	109
N—C4—C3	113 (1)	S—C6—H12	109
Pt—N—H1	107	S—C6—H13	109
O1—N—H1	108	H11—C6—H12	110
C4—N—H1	107	H11—C6—H13	109
O1—C1—H2	109	H12—C6—H13	110
O1—C1—H3	109
Pt—N—O1—C1	−167.5 (7)	Cl2—Pt—S—C6	−136.2 (6)
Pt—N—C4—C3	−170.9 (9)	Cl2—Pt—N—O1	126.3 (6)
Cl1—Pt—S—O2	−77.5 (4)	Cl2—Pt—N—C4	−110.2 (9)
Cl1—Pt—S—C5	157.4 (6)	O1—N—C4—C3	−47 (1)
Cl1—Pt—S—C6	45.8 (6)	O1—C1—C2—C3	14 (2)
Cl1—Pt—N—O1	−55.6 (6)	N—O1—C1—C2	−48 (1)
Cl1—Pt—N—C4	67.9 (9)	N—C4—C3—C2	14 (2)
Cl2—Pt—S—O2	100.5 (4)	C1—O1—N—C4	65 (1)
Cl2—Pt—S—C5	−24.6 (6)	C1—C2—C3—C4	2 (2)