cis-Dichlorido(dimethyl sulfoxide-κS)(N,N,N′,N′-tetra­methyl­guanidine-κN′′)platinum(II)

Eliseev, I.I.; Bokach, N.A.; Haukka, M.; Golenya, I.A.

doi:10.1107/S160053681300130X

metal-organic compounds

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ISSN: 2056-9890

Volume 69| Part 2| February 2013| Pages m117-m118

doi:10.1107/S160053681300130X

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cis-Dichlorido(dimethyl sulfoxide-κS)(N,N,N′,N′-tetramethylguanidine-κN′′)platinum(II)

Ivan I. Eliseev,^a Nadezhda A. Bokach,^a Matti Haukka ^b and Irina A. Golenya ^c ^*

^aDepartment of Chemistry, St Petersburg State University, 198504 Petrodvorets, Russian Federation, ^bUniversity of Joensuu, Department of Chemistry, PO Box, 111, FI-80101 Joensuu, Finland, and ^cKiev National Taras Shevchenko University, Department of Chemistry, Volodymyrska Str. 64, 01601 Kiev, Ukraine
^*Correspondence e-mail: igolenya@ua.fm

(Received 17 December 2012; accepted 13 January 2013; online 19 January 2013)

In the title compound, cis-[PtCl₂(C₅H₁₃N₃)(C₂H₆OS)], the four-coordinate Pt^II atom is bonded to one N atom of the N,N,N′,N′-tetramethylguanidine ligand, one dimethyl sulfoxide S atom and two chloride ligands, forming a cis-square-planar geometry. The bond lengths and angles of the N—Pt—Cl functionality are typical for imine dichloridoplatinum(II) complexes. The H atom of the imino group is oriented towards the O atom of the sulfoxide group of a neighboring molecule and forms an N—H⋯O hydrogen bond.

Related literature

For guanidines serving as nucleophiles towards metal-activated nitriles at Pt^II and Pt^IV atoms, see: Gushchin et al. (2007 , 2008 ); Tyan et al. (2008 ). For related structures, see: Bokach et al. (2003 ); Fairlie et al. (1997 ); Gonzalez et al. (2002 ); Makarycheva-Mikhailova et al. (2003 ). For a description of the Cambridge Structural Database, see: Allen (2002 ). For standard bond lengths, see: Allen et al. (1987 ).

Experimental

Crystal data

[PtCl₂(C₅H₁₃N₃)(C₂H₆OS)]
M_r = 459.30
Monoclinic, C c
a = 10.1577 (5) Å
b = 19.1711 (8) Å
c = 8.6536 (3) Å
β = 119.304 (2)°
V = 1469.51 (11) Å³
Z = 4
Mo Kα radiation
μ = 10.04 mm⁻¹
T = 120 K
0.24 × 0.13 × 0.12 mm

Data collection

Nonius KappaCCD diffractometer
Absorption correction: multi-scan (DENZO/SCALEPACK; Otwinowski & Minor, 1997 ) T_min = 0.151, T_max = 0.299
12560 measured reflections
3280 independent reflections
3044 reflections with I > 2σ(I)
R_int = 0.041

Refinement

R[F² > 2σ(F²)] = 0.023
wR(F²) = 0.045
S = 1.03
3280 reflections
142 parameters
2 restraints
H-atom parameters constrained
Δρ_max = 1.49 e Å⁻³
Δρ_min = −1.64 e Å⁻³
Absolute structure: Flack (1983 ), 1598 Friedel pairs
Flack parameter: 0.008 (6)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1ⁱ	0.86	2.21	3.021 (5)	159
Symmetry code: (i) $[x, -y, z+{\script{1\over 2}}]$ .

Data collection: COLLECT (Nonius, 1998 ); cell refinement: DENZO/SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO/SCALEPACK; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 2007 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053681300130X/hg5281sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681300130X/hg5281Isup2.hkl

checkCIF report

Comment top

As a part of our ongoing investigations on structural features of platinum complexes with guanidines (Gushchin et al., 2007; Gushchin et al., 2008) a new compound, (I), having PtII-bound N,N,N',N'-tetramethylguanidine, has been prepared and herein we report its X-ray crystal and molecular structures.

In the compound, the four-coordinate Pt atom has a distorted cis-square planar geometry where the Pt atom is bonded by one N atom of the N,N,N',N'-tetramethylguanidine ligand and one S atom of the dimethyl sulfoxide and two chlorides in the cis-position (Fig. 1 and Table 1). The values of the Pt–Cl bond distances (2.3214 (13) and 2.327 (2) Å) agree well with those of previously characterized platinum(II) chloride compounds (Makarycheva-Mikhailova et al., 2003; Gonzalez et al., 2002). The Pt–N bonds [2.013 (4) Å for Pt–N_imine] are in accord with those found in cis-/trans-[Pt(NH₃)₂{NH=C(NH₂)NMe₂}] (2.031 (9)/2.020 (3) Å), (Tyan et al., 2008), [Pt{NH=C(NH₂)NMe₂}(dien)][SO₃CF₃]₂ (2.018 (7) Å), (Fairlie et al., 1997) and [PtCl₄{NH=C(NMe₂)OC(NMe₂)=NH}] (2.015 (5) Å) (Bokach et al., 2003).

The C=N bond length (C(1)–N(1) 1.316 (6) Å) is equal, within 3σ, to the average C=N double bond distance (1.31 Å) obtained from the Cambridge Crystal Structural Database (Version 5.27; Allen, 2002). The bond lengths C(1)–N(2) and C(1)–N(3) [1.342 (7) and 1.352 (6) Å, respectively] have values closer to a typical C–N single bond [Nsp²–Csp² in amides 1.346 (11) Å] (Allen, 1987). In addition, the C=N bond length (1.316 (6) Å) and the C–N bonds lengths (C(1)–N(2) 1.342 (7), C(1)–N(3) 1.352 (6) Å) exhibit values typical, within 3σ, for the (amidine)₂Pt^II complexes, viz. [Pt{NH=C(NH₂)NMe₂}(dien)]²⁺, (1.31 (1), 1.394 (8) and 1.33 (1) Å) (Fairlie et al., 1997), and cis-/trans-[Pt(NH₃)₂{NH=C(NH₂)NMe₂}] (1.284 (14)/1.288 (5), 1.364 (14)/1.352 (5) and 1.364 (14)/1.341 (5) Å), (Tyan et al., 2008). The H atom of the imino function is oriented towards the O atom of the sulfoxide group of the neighboring molecule forming the intermolecular hydrogen bond (Figure 2, Table 2).

Related literature top

For guanidines serving as nucleophiles towards metal-activated nitriles at Pt^II and Pt^IV atoms, see: Gushchin et al. (2007, 2008); Tyan et al. (2008). For related structures, see: Bokach et al. (2003); Fairlie et al. (1997); Gonzalez et al. (2002); Makarycheva-Mikhailova et al. (2003). For a description of the Cambridge Structural Database, see; Allen (2002). For standard bond lengths, see: Allen et al. (1987).

Experimental top

N,N,N',N'-Tetramethylguanidine (13.8 g, 0.12 mmol) was added to K[PtCl₃(DMSO)] (50.0 mg, 0.12 mmol) in water (1 mL) and the reaction mixture was kept at room temperature for 2 h. The yellow crystalline precipitate were mechanically separated and subjected to the X-ray study. IR (KBr, selected bands, cm–1): 3008 (m, N–H), 1616 (s, C=N), 1134 (s, S=O); 1H NMR (CDCl3, δ, p.p.m.): 4.40 (s, br, 1H, =NH), 3,40 (s, 6H, Me2SO), 3.00 (s, br, 12H, Me2N–); Analyses calculated for C₇H₁₉N₃Cl₂OPtS: C 18.31, H 4.17, N 9.15%; found: C 18.05, H 4.15, N 8.59%.

Computing details top

Data collection: COLLECT (Nonius, 1998); cell refinement: DENZO/SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO/SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 2007); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. Molecular structure of (I), showing the atom-numbering scheme with displacement ellipsoids drawn at the 50% probability level.
	Fig. 2. Molecular structure of (I), showing the intermolecular hydrogen bond.

cis-Dichlorido(dimethyl sulfoxide-κS)(N,N,N',N'- tetramethylguanidine)platinum(II) top

Crystal data top

[PtCl₂(C₅H₁₃N₃)(C₂H₆OS)]	F(000) = 872
M_r = 459.30	D_x = 2.076 Mg m⁻³
Monoclinic, Cc	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2yc	Cell parameters from 6239 reflections
a = 10.1577 (5) Å	θ = 1.0–27.5°
b = 19.1711 (8) Å	µ = 10.04 mm⁻¹
c = 8.6536 (3) Å	T = 120 K
β = 119.304 (2)°	Block, pale yellow
V = 1469.51 (11) Å³	0.24 × 0.13 × 0.12 mm
Z = 4

Data collection top

Nonius KappaCCD diffractometer	3280 independent reflections
Radiation source: fine-focus sealed tube	3044 reflections with I > 2σ(I)
Horizontally mounted graphite crystal monochromator	R_int = 0.041
Detector resolution: 9 pixels mm^-1	θ_max = 27.5°, θ_min = 3.4°
ϕ scans and ω scans with κ offset	h = −13→13
Absorption correction: multi-scan (DENZO/SCALEPACK; Otwinowski & Minor, 1997)	k = −24→24
T_min = 0.151, T_max = 0.299	l = −11→11
12560 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.023	H-atom parameters constrained
wR(F²) = 0.045	w = 1/[σ²(F_o²) + (0.P)²] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max = 0.002
3280 reflections	Δρ_max = 1.49 e Å⁻³
142 parameters	Δρ_min = −1.64 e Å⁻³
2 restraints	Absolute structure: Flack (1983), 1598 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.008 (6)

Crystal data top

[PtCl₂(C₅H₁₃N₃)(C₂H₆OS)]	V = 1469.51 (11) Å³
M_r = 459.30	Z = 4
Monoclinic, Cc	Mo Kα radiation
a = 10.1577 (5) Å	µ = 10.04 mm⁻¹
b = 19.1711 (8) Å	T = 120 K
c = 8.6536 (3) Å	0.24 × 0.13 × 0.12 mm
β = 119.304 (2)°

Data collection top

Nonius KappaCCD diffractometer	3280 independent reflections
Absorption correction: multi-scan (DENZO/SCALEPACK; Otwinowski & Minor, 1997)	3044 reflections with I > 2σ(I)
T_min = 0.151, T_max = 0.299	R_int = 0.041
12560 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.023	H-atom parameters constrained
wR(F²) = 0.045	Δρ_max = 1.49 e Å⁻³
S = 1.03	Δρ_min = −1.64 e Å⁻³
3280 reflections	Absolute structure: Flack (1983), 1598 Friedel pairs
142 parameters	Absolute structure parameter: 0.008 (6)
2 restraints

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

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 > 2sigma(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) top

	x	y	z	U_iso*/U_eq
Pt1	0.96648 (6)	0.110788 (7)	1.03671 (6)	0.01299 (6)
Cl1	1.20421 (15)	0.15985 (7)	1.14273 (16)	0.0221 (3)
Cl2	0.9945 (3)	0.11372 (8)	1.3201 (3)	0.0229 (6)
S1	0.9352 (2)	0.10943 (7)	0.7678 (3)	0.0133 (5)
O1	0.7956 (4)	0.07948 (18)	0.6268 (4)	0.0197 (7)
N1	0.7691 (5)	0.0608 (2)	0.9550 (5)	0.0172 (9)
H1N	0.7766	0.0172	0.9792	0.026*
N2	0.5880 (5)	0.1425 (2)	0.7857 (6)	0.0201 (9)
N3	0.5363 (5)	0.0249 (2)	0.7283 (5)	0.0170 (9)
C1	0.6341 (6)	0.0760 (3)	0.8237 (6)	0.0162 (10)
C2	0.6478 (7)	0.1974 (3)	0.9182 (7)	0.0281 (12)
H2A	0.6875	0.1769	1.0365	0.042*
H2B	0.5671	0.2305	0.8972	0.042*
H2C	0.7291	0.2218	0.9105	0.042*
C3	0.4915 (7)	0.1652 (3)	0.6032 (7)	0.0329 (13)
H3A	0.4858	0.1281	0.5220	0.049*
H3B	0.5340	0.2074	0.5807	0.049*
H3C	0.3901	0.1752	0.5843	0.049*
C4	0.5856 (6)	−0.0446 (2)	0.7127 (6)	0.0201 (11)
H4A	0.6924	−0.0432	0.7446	0.030*
H4B	0.5253	−0.0610	0.5904	0.030*
H4C	0.5723	−0.0764	0.7926	0.030*
C5	0.3737 (6)	0.0318 (3)	0.6638 (8)	0.0300 (13)
H5A	0.3546	0.0749	0.7105	0.045*
H5B	0.3384	−0.0082	0.7039	0.045*
H5C	0.3197	0.0334	0.5340	0.045*
C6	0.9526 (7)	0.1948 (3)	0.7012 (7)	0.0250 (12)
H6A	0.9526	0.1926	0.5880	0.038*
H6B	1.0473	0.2157	0.7914	0.038*
H6C	0.8674	0.2234	0.6872	0.038*
C7	1.0888 (6)	0.0668 (3)	0.7656 (6)	0.0189 (11)
H7A	1.0886	0.0174	0.7943	0.028*
H7B	1.1836	0.0884	0.8537	0.028*
H7C	1.0791	0.0711	0.6477	0.028*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Pt1	0.01236 (9)	0.01404 (8)	0.01011 (8)	−0.00112 (17)	0.00359 (6)	−0.00035 (14)
Cl1	0.0163 (6)	0.0239 (6)	0.0214 (6)	−0.0052 (5)	0.0056 (5)	−0.0047 (5)
Cl2	0.0297 (13)	0.0281 (12)	0.0108 (10)	−0.0039 (8)	0.0099 (9)	−0.0004 (6)
S1	0.0130 (10)	0.0138 (10)	0.0105 (9)	0.0002 (6)	0.0037 (8)	0.0016 (6)
O1	0.018 (2)	0.0257 (19)	0.0129 (17)	0.0000 (15)	0.0058 (15)	−0.0009 (14)
N1	0.021 (2)	0.016 (2)	0.013 (2)	−0.0045 (17)	0.0072 (18)	0.0003 (16)
N2	0.016 (2)	0.018 (2)	0.022 (2)	0.0048 (18)	0.0057 (19)	0.0029 (18)
N3	0.010 (2)	0.019 (2)	0.020 (2)	−0.0008 (17)	0.0053 (18)	−0.0029 (17)
C1	0.013 (3)	0.022 (3)	0.016 (2)	−0.001 (2)	0.009 (2)	0.002 (2)
C2	0.027 (3)	0.021 (3)	0.030 (3)	0.005 (2)	0.008 (3)	−0.002 (2)
C3	0.026 (3)	0.029 (3)	0.026 (3)	0.002 (3)	−0.001 (3)	0.006 (2)
C4	0.019 (3)	0.019 (3)	0.017 (2)	0.000 (2)	0.006 (2)	−0.006 (2)
C5	0.014 (3)	0.032 (3)	0.044 (4)	−0.003 (2)	0.014 (3)	−0.010 (3)
C6	0.029 (3)	0.021 (3)	0.021 (3)	0.001 (2)	0.009 (2)	0.005 (2)
C7	0.016 (3)	0.019 (3)	0.017 (2)	0.004 (2)	0.004 (2)	−0.002 (2)

Geometric parameters (Å, º) top

Pt1—N1	2.013 (4)	C2—H2C	0.9800
Pt1—S1	2.189 (2)	C3—H3A	0.9800
Pt1—Cl1	2.3214 (13)	C3—H3B	0.9800
Pt1—Cl2	2.327 (2)	C3—H3C	0.9800
S1—O1	1.462 (4)	C4—H4A	0.9800
S1—C7	1.769 (5)	C4—H4B	0.9800
S1—C6	1.773 (5)	C4—H4C	0.9800
N1—C1	1.316 (6)	C5—H5A	0.9800
N1—H1N	0.8556	C5—H5B	0.9800
N2—C1	1.342 (7)	C5—H5C	0.9800
N2—C2	1.452 (7)	C6—H6A	0.9800
N2—C3	1.459 (7)	C6—H6B	0.9800
N3—C1	1.352 (6)	C6—H6C	0.9800
N3—C4	1.451 (6)	C7—H7A	0.9800
N3—C5	1.467 (6)	C7—H7B	0.9800
C2—H2A	0.9800	C7—H7C	0.9800
C2—H2B	0.9800

N1—Pt1—S1	91.13 (12)	N2—C3—H3A	109.5
N1—Pt1—Cl1	175.21 (12)	N2—C3—H3B	109.5
S1—Pt1—Cl1	90.38 (7)	H3A—C3—H3B	109.5
N1—Pt1—Cl2	88.20 (12)	N2—C3—H3C	109.5
S1—Pt1—Cl2	178.66 (11)	H3A—C3—H3C	109.5
Cl1—Pt1—Cl2	90.38 (7)	H3B—C3—H3C	109.5
O1—S1—C7	108.1 (2)	N3—C4—H4A	109.5
O1—S1—C6	107.6 (3)	N3—C4—H4B	109.5
C7—S1—C6	101.2 (3)	H4A—C4—H4B	109.5
O1—S1—Pt1	117.94 (19)	N3—C4—H4C	109.5
C7—S1—Pt1	110.29 (19)	H4A—C4—H4C	109.5
C6—S1—Pt1	110.4 (2)	H4B—C4—H4C	109.5
C1—N1—Pt1	129.5 (3)	N3—C5—H5A	109.5
C1—N1—H1N	111.0	N3—C5—H5B	109.5
Pt1—N1—H1N	115.1	H5A—C5—H5B	109.5
C1—N2—C2	122.2 (4)	N3—C5—H5C	109.5
C1—N2—C3	121.1 (4)	H5A—C5—H5C	109.5
C2—N2—C3	116.1 (4)	H5B—C5—H5C	109.5
C1—N3—C4	122.5 (4)	S1—C6—H6A	109.5
C1—N3—C5	121.4 (4)	S1—C6—H6B	109.5
C4—N3—C5	115.0 (4)	H6A—C6—H6B	109.5
N1—C1—N2	120.9 (5)	S1—C6—H6C	109.5
N1—C1—N3	120.7 (4)	H6A—C6—H6C	109.5
N2—C1—N3	118.4 (4)	H6B—C6—H6C	109.5
N2—C2—H2A	109.5	S1—C7—H7A	109.5
N2—C2—H2B	109.5	S1—C7—H7B	109.5
H2A—C2—H2B	109.5	H7A—C7—H7B	109.5
N2—C2—H2C	109.5	S1—C7—H7C	109.5
H2A—C2—H2C	109.5	H7A—C7—H7C	109.5
H2B—C2—H2C	109.5	H7B—C7—H7C	109.5

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1ⁱ	0.86	2.21	3.021 (5)	159

Symmetry code: (i) x, −y, z+1/2.

Experimental details

Crystal data
Chemical formula	[PtCl₂(C₅H₁₃N₃)(C₂H₆OS)]
M_r	459.30
Crystal system, space group	Monoclinic, Cc
Temperature (K)	120
a, b, c (Å)	10.1577 (5), 19.1711 (8), 8.6536 (3)
β (°)	119.304 (2)
V (Å³)	1469.51 (11)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	10.04
Crystal size (mm)	0.24 × 0.13 × 0.12

Data collection
Diffractometer	Nonius KappaCCD diffractometer
Absorption correction	Multi-scan (DENZO/SCALEPACK; Otwinowski & Minor, 1997)
T_min, T_max	0.151, 0.299
No. of measured, independent and observed [I > 2σ(I)] reflections	12560, 3280, 3044
R_int	0.041
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.023, 0.045, 1.03
No. of reflections	3280
No. of parameters	142
No. of restraints	2
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.49, −1.64
Absolute structure	Flack (1983), 1598 Friedel pairs
Absolute structure parameter	0.008 (6)

Computer programs: COLLECT (Nonius, 1998), DENZO/SCALEPACK (Otwinowski & Minor, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), DIAMOND (Brandenburg, 2007).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1ⁱ	0.86	2.21	3.021 (5)	159.2

Symmetry code: (i) x, −y, z+1/2.

Acknowledgements

This work was supported by the State Fund for Fundamental Research of Ukraine (grant No. 11–03–90417), the Russian Foundation for Basic Research (grant Nos. 11-03-00483, 12-03-33071 and 12-03-31040), Saint Petersburg State University (for a research grant 2011–2013; 12.37.133.2011 and a grant for applied research 2012–2013; 12.39.1050.2012). Financial support from the State Fund for Fundamental Researches of Ukraine (grant No. GP/F36/032) is also gratefully acknowledged.

References

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Volume 69| Part 2| February 2013| Pages m117-m118

doi:10.1107/S160053681300130X

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metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

cis-Di­chlorido(di­methyl sulfoxide-κS)(N,N,N′,N′-tetra­methyl­guanidine-κN′′)platinum(II)

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

metal-organic compounds

cis-Dichlorido(dimethyl sulfoxide-κS)(N,N,N′,N′-tetramethylguanidine-κN′′)platinum(II)