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Acta Crystallogr Sect E Struct Rep Online. 2008 October 1; 64(Pt 10): m1325.
Published online 2008 September 27. doi:  10.1107/S1600536808030109
PMCID: PMC2959355

Chlorido(dimethyl sulfoxide-κS)[2-(2-pyrid­yl)phenyl-κ2 N,C 1]platinum(II)

Abstract

In the title compound, [Pt(C11H8N)Cl(C2H6OS)], the S atom of dimethyl sulfoxide is trans to the pyridyl N atom [Pt—S = 2.2181 (11) Å] and the chlorido ligand is trans to the carbon donor of 2-(2-pyrid­yl)phenyl [Pt—Cl = 2.4202 (10) Å]. The [2-(2-pyrid­yl)phen­yl]platinum(II) unit forms a one-dimensional stack along the c axis with two independent inter­planar separations of 3.44 (9) and 3.50 (2) Å.

Related literature

For background information, see: Herber et al. (1994 [triangle]); Mdleleni et al. (1995 [triangle]); Newman et al. (2007 [triangle]); Ozawa et al. (2006 [triangle], 2007 [triangle]); Sakai & Ozawa (2007 [triangle]); Sakai et al. (1993 [triangle]); Ozawa & Sakai (2007 [triangle]); Kobayashi et al. (2008 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-m1325-scheme1.jpg

Experimental

Crystal data

  • [Pt(C11H8N)Cl(C2H6OS)]
  • M r = 462.85
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-m1325-efi1.jpg
  • a = 22.414 (3) Å
  • b = 10.0205 (16) Å
  • c = 14.057 (2) Å
  • β = 124.512 (2)°
  • V = 2601.6 (7) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 11.14 mm−1
  • T = 100 (2) K
  • 0.09 × 0.08 × 0.04 mm

Data collection

  • Bruker SMART APEXII CCD-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.486, T max = 0.640
  • 7004 measured reflections
  • 2850 independent reflections
  • 2448 reflections with I > 2σ(I)
  • R int = 0.018

Refinement

  • R[F 2 > 2σ(F 2)] = 0.023
  • wR(F 2) = 0.064
  • S = 1.11
  • 2850 reflections
  • 165 parameters
  • H-atom parameters constrained
  • Δρmax = 2.05 e Å−3
  • Δρmin = −1.43 e Å−3

Data collection: APEX2 (Bruker, 2006 [triangle]); cell refinement: APEX2; data reduction: SAINT (Bruker, 2004 [triangle]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: KENX (Sakai, 2004 [triangle]); software used to prepare material for publication: SHELXL97, TEXSAN (Molecular Structure Corporation, 2001 [triangle]), KENX and ORTEPII (Johnson, 1976 [triangle]).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808030109/at2633sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808030109/at2633Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

This work was in part supported by a Grant-in-Aid for Scientific Research (A) (No. 17205008), a Grant-in-Aid for Specially Promoted Research (No. 18002016), and a Grant-in-Aid for the Global COE Program (‘Science for Future Molecular Systems’) from the Ministry of Education, Culture, Sports, Science, and Technology of Japan.

supplementary crystallographic information

Comment

Interests over many years have concentrated on the molecular catalysis of PtII complexes in photochemical hydrogen production from water (Sakai et al., 1993; Ozawa et al., 2006; Sakai & Ozawa, 2007; Ozawa, Yokoyama et al., 2007). The results obtained so far suggest that destabilization of the HOMO, which generally corresponds to the filled PtII dz2 orbital, gives rise to the higher H2-evolving activity of the complexes (Sakai & Ozawa, & Sakai, 2007). It has also been ascertained that the mononuclear PtII complexes possessing a cis-PtCl2 unit, such as cis-PtCl2(NH3)2, PtCl2(4,4'-dicarboxy-2,2'-bipyridine), and PtCl2(2,2'-bipyrimidine), exhibit considerably higher H2-evolving activity in comparison with those only having the amine or pyridyl type of neutral ligands, such as [Pt(NH3)4]2+ and [Pt(bpy)2]2+ (Ozawa, Yokoyama et al., 2007). In this context, the 2-phenylpyridinate (ppy) ligand was selected because of the well known strong σ-donating character of the C(ppy) donor, expecting the higher energy level of the HOMO for the PtII(ppy) complexes. As a result, the first water-soluble salt of [Pt(ppy)Cl2]-, that is, [K(18-crown-6)][Pt(ppy)Cl2].0.5H2O (18-crown-6 = 1,4,7,10,13,16-hexaoxacyclooctadecane) [abbreviated as compound (II)], was recently prepared in our group and its catalytic activity in photochemical hydrogen production from water was examined in detail (Kobayashi et al., in submission). The title compound, Pt(ppy)Cl(DMOS-S) (DMSO = dimethyl sulfoxide) [abbreviated as compound (I)], was first prepared from recrystallization of (II) from DMSO, but an improved synthetic route is reported in this work (see Experimental Section). It has been ascertained that the H2-evolving activity of (I) is much lower than that of (II), the reason for which remains ambiguous at the moment.

The donor atoms, except for the sulfur atom S1, comprise a planar geometry and the Pt atom (Pt1) does not deviate from this plane at all. The four-atom r.m.s. deviation, given in the best-plane calculation for the plane defined by atoms N1, C11, Cl1, and Pt1, was negligible (0.0003). Hereafter, this plane is defined as the Pt coordination plane. The sulfur atom (S1) and the oxygen atom (O1) of DMSO are only slightly shifted out of this plane by 0.067 (5) and 0.045 (8) Å, respectively. The torsion angles given by C11—Pt1—S1—O1 = 2.4 (2) and Cl1—Pt1—S1—O1 = -177.83 (17)° also reveal that the oxygen atom of DMSO is not largely shifted out of the coordination plane. Thus, it can be considered that (I) adopts a pseudo mirror symmetry. The benzene ring consisting of atoms C6—C11 is nearly coplanar with the coordination plane, where the dihedral angle between the benzene and the coordination planes is calculated as 0.7 (2)°. The pyridyl plane defined by atoms N1 and C1—C5 is slightly declined with respect to the coordination plane by 2.8 (2)°. The dihedral angle between the two aromatic rings is 2.5 (2)°.

The ppy ligand in compound (I, Fig. 1) does not suffer from any disorder problem. Indeed, there is a clear difference in the bond lengths of Pt—N(ppy) and Pt—C(ppy); Pt1—N1 = 2.069 (3) and Pt1—C11 = 2.002 (4) Å. Because of the strong trans influence originated by the C(ppy) donor, Pt1—Cl1 distance [2.4202 (10) Å] is longer than those reported for PtCl2(2,2'-bipyridine) [2.281 (4) - 2.306 (2) Å; Herber et al., 1994]. Th Pt1—Cl1 distance is comparable to the value reported for Pt(ppy)(Hppy)Cl [2.4145 (23) Å; Mdleleni et al., 1995]. In addition, the Pt1—S1 bond distance [2.2181 (11) Å], in the position trans to the N(ppy) donor, is comparable to those previously reported for Pt(2-(4-fluorophenyl)pyridine)Cl(DMSO) [2.2161 (16) Å; Newman et al., 2007].

On the other hand, compound (I) forms a one-dimensional stack along the c axis based on the π-π stacking interactions between the phenylpyridinatoplatinum(II) units (see Fig. 2). The separation between the two adjacent planes is estimated as 3.44 (9) Å for the stack shown in Fig. 4 and 3.50 (2) Å for that in Fig. 5. In the former (Fig. 4), atoms C1i, C5i, N1i, and Pt1i have an interaction to the phenylpyridinate moiety originally located and therefore shifts of these atoms from the best plane defined by atoms N1 and C1—C11 are used to calculate the separation of the two stacked planes at this geometry. In the latter (Fig. 5), atoms N1ii, C1ii, Cii2, C5ii, C6ii, C10ii, C11ii, and Pt1ii are involved in the π-stacking association and their shifts from the best plane defined by atoms N1 and C1—C11 are similarly used to calculate the separation at this geometry. In these geometries, strong d-π interactions also contribute to the stabilization of stacking associations [Pt1—C4i = 3.525 (4) and Pt1—C4ii = 3.523 (4) Å; symmetry codes: (i) -x, y, 0.5 - z; (ii) -x, 1 - y, 1 - z]. Finally, it must be noted that metal-metal interactions are unimportant in this crystal [Pt1—Pt1i = 5.9946 (8) and Pt1—Pt1ii = 5.4225 (9) Å], where the symmetry operations are same to those given in Fig. 4 and Fig. 5.

Experimental

A mixture of cis-PtCl2(DMSO)2 (0.21 g, 0.50 mmol) and 2-phenylpyridine (0.078 g, 0.50 mmol) in methanol (10 ml) was sealed in a pressure-resistant vial and was stirred at 393 K for 3 h. After the solution was cooled down to room temperature, the yellow precipitate of compound (I) was filtrated and dried in vacuo (Caution! Do not open the vial while it is hot, since the solution splashes out because of the violent boiling phenomenon upon a sudden decrease in pressure). Yield: 0.14 g (60%). Analysis calculated for C13H14ClNOPtS: C 33.73, H 3.05, N 3.03. Found: C 33.95, H 2.99, N 3.02. 1H NMR (300.53 MHz, acetone-d6), p.p.m.: δ 9.63 [d, J = 5.97 Hz, 3J(195Pt-1H) = 17.8 Hz, 1H], 8.37 [d, J = 6.81 Hz, 3J(195Pt-1H) = 22.8 Hz, 1H], 8.16–8.06 (m, 2H), 7.25 (d, J = 6.46 Hz), 7.48 (t, J = 6.43 Hz), 7.20–7.11 (m, 2H), 3.63 [s, 3J(195Pt-1H) = 12.2 Hz, 6H]. A good quality single-crystal was prepared by diffusion of methanol into a DMSO solution of (I).

Refinement

All H atoms were placed in idealized positions (methyl C—H = 0.98 Å and aromatic C—H = 0.95 Å), and included in the refinement in a riding-model approximation, with Uiso(H) = 1.5Ueq(methyl C) and Uiso(H) = 1.2Ueq(aromatic C). In the final difference Fourier map, the highest peak was located 0.83 Å from atom Pt1. The deepest hole was located 1.07 Å from atom H9.

Figures

Fig. 1.
The molecular structure of (I) showing the atom-labeling scheme. Displacement ellipsoids are drawn at the 50% probability level.
Fig. 2.
Views down the c axis, showing the manner how the phenylpyridinatoplatinum(II) units are stacked along the c axis to give a one-dimensoinal network. Hydrogen atoms are omitted for clarity.
Fig. 3.
Views down the b axis, showing the manner how the phenylpyridinatoplatinum(II) units are stacked along the c axis to give a one-dimensoinal network. Hydrogen atoms are omitted for clarity.
Fig. 4.
Views perpendicular to the aromatic systems that are stacked at two independent geometries [Symmetry code: (i) -x, y, 0.5 - z].
Fig. 5.
Views perpendicular to the aromatic systems that are stacked at two independent geometries [Symmetry code: (ii) -x, 1 - y, 1 - z].

Crystal data

[Pt(C11H8N)Cl(C2H6OS)]F(000) = 1744
Mr = 462.85Dx = 2.363 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 3936 reflections
a = 22.414 (3) Åθ = 2.5–27.9°
b = 10.0205 (16) ŵ = 11.14 mm1
c = 14.057 (2) ÅT = 100 K
β = 124.512 (2)°Prisms, yellow
V = 2601.6 (7) Å30.09 × 0.08 × 0.04 mm
Z = 8

Data collection

Bruker SMART APEX CCD-detector diffractometer2850 independent reflections
Radiation source: rotating anode with a mirror focusing unit2448 reflections with I > 2σ(I)
graphiteRint = 0.018
[var phi] and ω scansθmax = 27.1°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −28→28
Tmin = 0.486, Tmax = 0.640k = −12→9
7004 measured reflectionsl = −18→15

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.023Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.064H-atom parameters constrained
S = 1.11w = 1/[σ2(Fo2) + (0.0295P)2 + 15.2156P] where P = (Fo2 + 2Fc2)/3
2850 reflections(Δ/σ)max = 0.002
165 parametersΔρmax = 2.05 e Å3
0 restraintsΔρmin = −1.43 e Å3

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.Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane)-14.3368 (0.0269) x - 0.3580 (0.0127) y + 13.9887 (0.0034) z = 5.0906 (0.0091)* 0.0000 (0.0001) N1 * -0.0003 (0.0009) C11 * -0.0002 (0.0007) Cl1 * 0.0004 (0.0015) Pt1 - 0.0669 (0.0049) S1 - 0.0453 (0.0077) O1Rms deviation of fitted atoms = 0.0003-15.0609 (0.0266) x - 0.5670 (0.0181) y + 13.9054 (0.0039) z = 4.9585 (0.0082)Angle to previous plane (with approximate e.s.d.) = 2.77 (0.16)* -0.0032 (0.0026) N1 * 0.0072 (0.0030) C1 * -0.0025 (0.0030) C2 * -0.0058 (0.0029) C3 * 0.0096 (0.0029) C4 * -0.0052 (0.0027) C5 - 0.1020 (0.0055) Pt1Rms deviation of fitted atoms = 0.0061-14.3427 (0.0315) x - 0.4723 (0.0194) y + 13.9812 (0.0035) z = 5.0095 (0.0158)Angle to previous plane (with approximate e.s.d.) = 2.52 (0.18)* -0.0053 (0.0030) C6 * 0.0050 (0.0034) C7 * 0.0011 (0.0036) C8 * -0.0071 (0.0033) C9 * 0.0068 (0.0030) C10 * -0.0006 (0.0029) C11 0.0196 (0.0064) Pt1Rms deviation of fitted atoms = 0.0050-14.3368 (0.0269) x - 0.3580 (0.0127) y + 13.9887 (0.0034) z = 5.0906 (0.0091)Angle to previous plane (with approximate e.s.d.) = 0.66 (0.17)* 0.0000 (0.0001) N1 * -0.0003 (0.0009) C11 * -0.0002 (0.0007) Cl1 * 0.0004 (0.0015) Pt1 - 0.0669 (0.0049) S1 - 0.0453 (0.0077) O1Rms deviation of fitted atoms = 0.0003-14.6775 (0.0205) x - 0.4790 (0.0073) y + 13.9524 (0.0028) z = 4.9852 (0.0045)Angle to previous plane (with approximate e.s.d.) = 1.36 (0.14)* 0.0328 (0.0031) N1 * 0.0226 (0.0035) C1 * -0.0212 (0.0037) C2 * -0.0380 (0.0034) C3 * -0.0016 (0.0037) C4 * 0.0177 (0.0038) C5 * 0.0052 (0.0039) C6 * 0.0303 (0.0041) C7 * 0.0139 (0.0042) C8 * -0.0215 (0.0039) C9 * -0.0223 (0.0033) C10 * -0.0180 (0.0035) C11 - 3.4480 (0.0042) N1_$1 - 3.3136 (0.0062) C1_$1 - 3.5267 (0.0045) C5_$1 - 3.4606 (0.0029) Pt1_$1Rms deviation of fitted atoms = 0.0228-14.6775 (0.0205) x - 0.4790 (0.0073) y + 13.9524 (0.0028) z = 4.9852 (0.0045)Angle to previous plane (with approximate e.s.d.) = 0.00 (0.12)* 0.0328 (0.0031) N1 * 0.0226 (0.0035) C1 * -0.0212 (0.0037) C2 * -0.0380 (0.0034) C3 * -0.0016 (0.0037) C4 * 0.0177 (0.0038) C5 * 0.0052 (0.0039) C6 * 0.0303 (0.0041) C7 * 0.0139 (0.0042) C8 * -0.0215 (0.0039) C9 * -0.0223 (0.0033) C10 * -0.0180 (0.0035) C11 3.4700 (0.0040) N1_$2 3.4803 (0.0050) C1_$2 3.5240 (0.0050) C2_$2 3.4851 (0.0048) C5_$2 3.4977 (0.0053) C6_$2 3.5252 (0.0047) C10_$2 3.5209 (0.0046) C11_$2 3.5174 (0.0022) Pt1_$2Rms deviation of fitted atoms = 0.0228
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 (Å2)

xyzUiso*/Ueq
Pt10.121378 (8)0.501904 (14)0.501179 (13)0.01100 (7)
Cl10.16776 (5)0.27601 (10)0.54289 (9)0.0177 (2)
S10.23482 (5)0.57296 (10)0.61446 (9)0.0135 (2)
O10.25415 (16)0.7153 (3)0.6395 (3)0.0207 (7)
N10.01517 (18)0.4393 (4)0.3907 (3)0.0130 (7)
C1−0.0056 (2)0.3097 (4)0.3637 (4)0.0188 (9)
H10.02980.24120.40030.023*
C2−0.0769 (2)0.2759 (4)0.2843 (4)0.0198 (9)
H2−0.09050.18490.26560.024*
C3−0.1290 (2)0.3759 (5)0.2317 (4)0.0179 (9)
H3−0.17840.35420.17640.021*
C4−0.1079 (3)0.5076 (4)0.2611 (4)0.0156 (9)
H4−0.14280.57710.22760.019*
C5−0.0353 (2)0.5373 (4)0.3399 (4)0.0128 (8)
C6−0.0046 (2)0.6714 (4)0.3759 (4)0.0141 (8)
C7−0.0479 (2)0.7861 (4)0.3361 (4)0.0226 (10)
H7−0.09900.77840.28410.027*
C8−0.0161 (3)0.9104 (5)0.3726 (5)0.0286 (11)
H8−0.04530.98850.34550.034*
C90.0584 (2)0.9211 (4)0.4488 (4)0.0216 (9)
H90.08041.00660.47320.026*
C100.1010 (2)0.8066 (4)0.4897 (4)0.0158 (8)
H100.15190.81550.54330.019*
C110.0714 (2)0.6793 (4)0.4545 (4)0.0128 (8)
C120.2791 (2)0.4911 (4)0.7508 (4)0.0183 (9)
H12A0.33120.50890.79480.027*
H12B0.27060.39480.73890.027*
H12C0.25980.52470.79380.027*
C130.2836 (3)0.5101 (4)0.5582 (4)0.0198 (10)
H13A0.26360.54860.48160.030*
H13B0.27910.41270.55190.030*
H13C0.33480.53460.61010.030*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Pt10.01044 (10)0.00879 (10)0.01265 (11)0.00073 (6)0.00587 (8)0.00039 (5)
Cl10.0155 (5)0.0109 (4)0.0218 (5)0.0024 (4)0.0076 (4)0.0010 (4)
S10.0114 (5)0.0116 (5)0.0152 (5)0.0004 (4)0.0062 (4)−0.0005 (4)
O10.0144 (15)0.0135 (15)0.0254 (17)−0.0006 (12)0.0061 (13)−0.0018 (13)
N10.0105 (16)0.0156 (17)0.0126 (16)0.0001 (15)0.0064 (14)0.0002 (14)
C10.019 (2)0.013 (2)0.020 (2)0.0007 (17)0.0082 (19)0.0022 (17)
C20.022 (2)0.013 (2)0.023 (2)−0.0050 (18)0.012 (2)−0.0042 (17)
C30.014 (2)0.021 (2)0.019 (2)−0.0037 (17)0.0096 (18)−0.0006 (17)
C40.017 (2)0.014 (2)0.017 (2)0.0010 (16)0.0104 (19)0.0008 (15)
C50.015 (2)0.0156 (19)0.0109 (19)0.0004 (17)0.0088 (17)0.0003 (16)
C60.015 (2)0.012 (2)0.015 (2)0.0003 (16)0.0081 (17)−0.0006 (15)
C70.017 (2)0.015 (2)0.032 (3)0.0022 (18)0.012 (2)0.0014 (19)
C80.021 (2)0.014 (2)0.041 (3)0.0067 (18)0.012 (2)0.003 (2)
C90.018 (2)0.012 (2)0.033 (3)−0.0042 (18)0.013 (2)−0.0027 (19)
C100.0127 (19)0.017 (2)0.016 (2)0.0009 (17)0.0064 (17)0.0016 (16)
C110.014 (2)0.0118 (18)0.015 (2)0.0023 (16)0.0100 (17)0.0014 (16)
C120.013 (2)0.021 (2)0.017 (2)0.0016 (16)0.0062 (19)0.0009 (16)
C130.017 (2)0.021 (2)0.025 (2)−0.0001 (17)0.014 (2)−0.0019 (17)

Geometric parameters (Å, °)

Pt1—C112.002 (4)C3—H30.9500
Pt1—N12.069 (3)C4—H40.9500
Pt1—S12.2181 (11)C5—C61.464 (6)
Pt1—Cl12.4202 (10)C6—C71.400 (6)
S1—O11.474 (3)C6—C111.413 (6)
S1—C121.782 (5)C7—C81.382 (6)
S1—C131.788 (5)C7—H70.9500
N1—C51.355 (6)C8—C91.386 (6)
N1—C11.359 (6)C8—H80.9500
C1—C21.377 (6)C9—C101.392 (6)
C2—C31.392 (6)C9—H90.9500
C3—C41.384 (6)C10—C111.393 (6)
C4—C51.385 (6)C10—H100.9500
Pt1—C4i3.525 (4)C12—H12A0.9800
Pt1—C4ii3.523 (4)C12—H12B0.9800
Pt1—Pt1i5.9946 (8)C12—H12C0.9800
Pt1—Pt1ii5.4225 (9)C13—H13A0.9800
C1—H10.9500C13—H13B0.9800
C2—H20.9500C13—H13C0.9800
C11—Pt1—N180.28 (16)C7—C6—C11121.5 (4)
C11—Pt1—S198.69 (12)C7—C6—C5122.1 (4)
N1—Pt1—S1177.97 (10)C11—C6—C5116.3 (4)
C11—Pt1—Cl1173.26 (12)C8—C7—C6119.8 (4)
N1—Pt1—Cl192.98 (10)C8—C7—H7120.1
S1—Pt1—Cl188.05 (4)C6—C7—H7120.1
O1—S1—C12106.22 (19)C7—C8—C9119.9 (4)
O1—S1—C13106.0 (2)C7—C8—H8120.0
C12—S1—C13101.9 (2)C9—C8—H8120.0
O1—S1—Pt1122.98 (13)C8—C9—C10120.0 (4)
C12—S1—Pt1109.74 (15)C8—C9—H9120.0
C13—S1—Pt1107.97 (16)C10—C9—H9120.0
C5—N1—C1119.6 (4)C9—C10—C11122.1 (4)
C5—N1—Pt1116.0 (3)C9—C10—H10119.0
C1—N1—Pt1124.4 (3)C11—C10—H10119.0
N1—C1—C2121.2 (4)C10—C11—C6116.7 (4)
N1—C1—H1119.4C10—C11—Pt1129.1 (3)
C2—C1—H1119.4C6—C11—Pt1114.2 (3)
C1—C2—C3119.5 (4)S1—C12—H12A109.5
C1—C2—H2120.2S1—C12—H12B109.5
C3—C2—H2120.2H12A—C12—H12B109.5
C4—C3—C2119.1 (4)S1—C12—H12C109.5
C4—C3—H3120.5H12A—C12—H12C109.5
C2—C3—H3120.5H12B—C12—H12C109.5
C3—C4—C5119.5 (4)S1—C13—H13A109.5
C3—C4—H4120.3S1—C13—H13B109.5
C5—C4—H4120.3H13A—C13—H13B109.5
N1—C5—C4121.2 (4)S1—C13—H13C109.5
N1—C5—C6113.2 (4)H13A—C13—H13C109.5
C4—C5—C6125.6 (4)H13B—C13—H13C109.5
C11—Pt1—S1—O12.4 (2)C4—C5—C6—C72.9 (7)
Cl1—Pt1—S1—O1−177.83 (17)N1—C5—C6—C111.3 (5)
C5—N1—C1—C20.9 (6)C4—C5—C6—C11−177.9 (4)
N1—C1—C2—C3−0.8 (7)C11—C6—C7—C80.9 (7)
C1—C2—C3—C4−0.4 (6)C5—C6—C7—C8−179.9 (4)
C2—C3—C4—C51.6 (6)C6—C7—C8—C9−0.3 (8)
C1—N1—C5—C40.3 (6)C7—C8—C9—C10−0.9 (7)
C1—N1—C5—C6−178.9 (4)C8—C9—C10—C111.4 (7)
C3—C4—C5—N1−1.5 (6)C9—C10—C11—C6−0.8 (6)
C3—C4—C5—C6177.5 (4)C7—C6—C11—C10−0.4 (6)
N1—C5—C6—C7−178.0 (4)C5—C6—C11—C10−179.6 (4)

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: AT2633).

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