Literature DB >> 21202820

Chlorido(dimethyl sulfoxide)(pyridine-2-thiol-ato N-oxide-κS,O)platinum(II).

B Ravindran Durai Nayagam, Samuel Robinson Jebas, P Selvarathy Grace, Dieter Schollmeyer.   

Abstract

The asymmetric unit of the title compound, [Pt(C(5)H(4)NOS)Cl(C(2)H(6)OS)], contains two independent complex mol-ecules having similar geometries. Each Pt(II) atom is four-coordinated in a distorted square-planar geometry by S and O atoms of one pyridine N-oxide ligand, the S atom of one dimethyl sulfoxide mol-ecule and one terminal Cl(-) ion. The mol-ecules are linked into a three-dimensional framework by C-H⋯O and C-H⋯Cl hydrogen bonds.

Entities:  

Year:  2008        PMID： 21202820      PMCID： PMC2961893          DOI： 10.1107/S1600536808019041

Source DB:  PubMed          Journal:  Acta Crystallogr Sect E Struct Rep Online        ISSN： 1600-5368


Related literature

For biological activities of platinum, see: Weiss & Christian (1993 ▶); Loehrer et al. (1988 ▶); For biological activities of N-oxide derivatives, see: Bovin et al. (1992 ▶); Katsuyuki et al. (1991 ▶); Leonard et al. (1955 ▶); Lobana & Bhatia (1989 ▶); Symons & West (1985 ▶). For related literature, see: Jebas et al. (2005 ▶); Ravindran et al. (2008 ▶); Dyksterhouse et al. (2000 ▶); Ohms et al. (1982 ▶); Ravindran et al. (2008 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

[Pt(C5H4NOS)Cl(C2H6OS)] M = 434.82 Triclinic, a = 10.2407 (5) Å b = 10.9703 (5) Å c = 10.9772 (6) Å α = 82.950 (1)° β = 76.720 (1)° γ = 76.554 (1)° V = 1164.21 (10) Å3 Z = 4 Mo Kα radiation μ = 12.61 mm−1 T = 173 (2) K 0.47 × 0.31 × 0.15 mm

Data collection

Bruker Kappa APEXII area-detector diffractometer Absorption correction: Gaussian (Coppens, 1970 ▶) T min = 0.5, T max = 1.0 22889 measured reflections 5542 independent reflections 5032 reflections with I > 2σ(I) R int = 0.034

Refinement

R[F 2 > 2σ(F 2)] = 0.028 wR(F 2) = 0.070 S = 1.03 5542 reflections 257 parameters H-atom parameters constrained Δρmax = 5.99 e Å−3 Δρmin = −1.02 e Å−3 Data collection: APEX2 (Bruker, 2006 ▶); cell refinement: APEX2; data reduction: SAINT (Bruker, 2006 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003 ▶). Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808019041/ci2615sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536808019041/ci2615Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
[Pt(C5H4NOS)Cl(C2H6OS)]Z = 4
Mr = 434.82F000 = 808
Triclinic, P1Dx = 2.481 Mg m−3
Hall symbol: -P 1Mo Kα radiation λ = 0.71073 Å
a = 10.2407 (5) ÅCell parameters from 9909 reflections
b = 10.9703 (5) Åθ = 2.5–27.8º
c = 10.9772 (6) ŵ = 12.61 mm−1
α = 82.950 (1)ºT = 173 (2) K
β = 76.720 (1)ºPlate, colourless
γ = 76.554 (1)º0.47 × 0.31 × 0.15 mm
V = 1164.21 (10) Å3
Bruker Kappa APEXII area-detector diffractometer5032 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.034
T = 173(2) Kθmax = 27.9º
ω and φ scansθmin = 1.9º
Absorption correction: Gaussian(Coppens, 1970)h = −13→13
Tmin = 0.5, Tmax = 1.0k = −14→14
22889 measured reflectionsl = −14→14
5542 independent reflections
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.028H-atom parameters constrained
wR(F2) = 0.070  w = 1/[σ2(Fo2) + (0.0265P)2 + 7.1392P] where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max = 0.001
5542 reflectionsΔρmax = 5.99 e Å−3
257 parametersΔρmin = −1.02 e Å−3
Primary atom site location: structure-invariant direct methodsExtinction correction: none
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.
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.
xyzUiso*/Ueq
Pt10.659125 (19)0.633021 (18)0.106453 (19)0.02604 (6)
Cl10.77432 (14)0.58127 (13)−0.09729 (13)0.0340 (3)
S10.55837 (15)0.66420 (15)0.30825 (14)0.0370 (3)
S20.48807 (13)0.75691 (12)0.03633 (12)0.0275 (3)
C10.6869 (6)0.5686 (5)0.3749 (5)0.0326 (11)
C20.6782 (7)0.5500 (6)0.5051 (6)0.0412 (14)
H20.59830.58970.56080.049*
C30.7857 (7)0.4741 (6)0.5520 (6)0.0435 (14)
H30.78050.46220.64010.052*
C40.9021 (7)0.4147 (6)0.4701 (6)0.0399 (13)
H40.97630.36180.50200.048*
C50.9085 (6)0.4330 (5)0.3449 (6)0.0343 (12)
H50.98750.39310.28840.041*
N60.8014 (5)0.5089 (4)0.2998 (4)0.0299 (9)
O70.8176 (4)0.5207 (4)0.1729 (4)0.0319 (8)
O80.3857 (4)0.8369 (4)0.1274 (4)0.0389 (10)
C90.5470 (6)0.8558 (5)−0.0944 (6)0.0355 (12)
H9A0.46860.9050−0.12820.053*
H9B0.61030.8044−0.15910.053*
H9C0.59460.9127−0.06820.053*
C100.4004 (6)0.6700 (6)−0.0310 (6)0.0373 (13)
H10A0.35680.61430.03440.056*
H10B0.46590.6197−0.09550.056*
H10C0.33000.7280−0.06930.056*
Pt20.23052 (2)−0.015106 (18)0.666962 (18)0.02707 (6)
Cl20.36326 (16)−0.21985 (13)0.65722 (14)0.0391 (3)
S30.10091 (15)0.17934 (13)0.69804 (14)0.0340 (3)
S40.23267 (14)0.00092 (13)0.46616 (13)0.0307 (3)
C110.0802 (5)0.1703 (5)0.8589 (5)0.0299 (11)
C12−0.0046 (6)0.2637 (5)0.9339 (6)0.0358 (12)
H12−0.05280.33750.89550.043*
C13−0.0197 (6)0.2510 (6)1.0616 (6)0.0384 (13)
H13−0.07840.31501.11160.046*
C140.0521 (6)0.1429 (6)1.1175 (6)0.0376 (13)
H140.04320.13311.20600.045*
C150.1349 (6)0.0516 (5)1.0449 (5)0.0314 (11)
H150.1839−0.02241.08240.038*
N160.1469 (4)0.0670 (4)0.9177 (4)0.0272 (9)
O170.2309 (4)−0.0305 (4)0.8508 (4)0.0315 (8)
O180.1467 (5)0.1149 (4)0.4162 (4)0.0430 (10)
C190.4043 (6)−0.0135 (6)0.3803 (5)0.0359 (12)
H19A0.4095−0.03300.29430.054*
H19B0.4645−0.08120.42060.054*
H19C0.43360.06570.37840.054*
C200.1896 (6)−0.1328 (6)0.4240 (6)0.0377 (13)
H20A0.0948−0.13590.46560.057*
H20B0.2517−0.20880.45020.057*
H20C0.1985−0.12790.33280.057*
U11U22U33U12U13U23
Pt10.02424 (10)0.02261 (10)0.02981 (11)−0.00326 (7)−0.00512 (7)−0.00053 (7)
Cl10.0327 (6)0.0314 (6)0.0334 (7)−0.0040 (5)−0.0012 (5)−0.0018 (5)
S10.0320 (7)0.0393 (8)0.0333 (7)0.0038 (6)−0.0052 (5)−0.0030 (6)
S20.0264 (6)0.0248 (6)0.0306 (6)−0.0041 (5)−0.0065 (5)0.0000 (5)
C10.033 (3)0.028 (3)0.035 (3)−0.006 (2)−0.005 (2)−0.001 (2)
C20.044 (3)0.042 (3)0.035 (3)−0.006 (3)−0.009 (3)0.001 (3)
C30.051 (4)0.046 (4)0.037 (3)−0.016 (3)−0.015 (3)0.007 (3)
C40.042 (3)0.036 (3)0.046 (3)−0.012 (3)−0.020 (3)0.004 (3)
C50.032 (3)0.027 (3)0.047 (3)−0.006 (2)−0.015 (2)0.000 (2)
N60.031 (2)0.025 (2)0.033 (2)−0.0056 (18)−0.0087 (18)0.0007 (18)
O70.0277 (18)0.031 (2)0.033 (2)0.0014 (15)−0.0066 (15)−0.0017 (16)
O80.036 (2)0.038 (2)0.037 (2)0.0083 (17)−0.0090 (17)−0.0050 (17)
C90.034 (3)0.025 (3)0.044 (3)−0.006 (2)−0.007 (2)0.008 (2)
C100.035 (3)0.033 (3)0.047 (3)−0.010 (2)−0.015 (3)0.003 (2)
Pt20.02632 (10)0.02645 (11)0.02760 (11)−0.00455 (8)−0.00562 (7)−0.00071 (7)
Cl20.0442 (8)0.0317 (7)0.0354 (7)0.0031 (6)−0.0071 (6)−0.0041 (5)
S30.0385 (7)0.0286 (7)0.0342 (7)−0.0022 (5)−0.0130 (6)0.0009 (5)
S40.0302 (6)0.0327 (7)0.0292 (6)−0.0079 (5)−0.0064 (5)0.0001 (5)
C110.027 (2)0.026 (3)0.038 (3)−0.006 (2)−0.009 (2)−0.003 (2)
C120.032 (3)0.026 (3)0.050 (3)−0.003 (2)−0.012 (2)−0.009 (2)
C130.034 (3)0.036 (3)0.046 (3)−0.001 (2)−0.009 (2)−0.016 (3)
C140.034 (3)0.042 (3)0.037 (3)−0.008 (2)−0.005 (2)−0.010 (2)
C150.029 (3)0.033 (3)0.033 (3)−0.007 (2)−0.009 (2)0.000 (2)
N160.023 (2)0.027 (2)0.031 (2)−0.0025 (17)−0.0061 (17)−0.0047 (17)
O170.0299 (19)0.0267 (19)0.035 (2)0.0031 (15)−0.0077 (15)−0.0055 (15)
O180.043 (2)0.047 (3)0.036 (2)−0.0002 (19)−0.0122 (18)0.0021 (19)
C190.034 (3)0.043 (3)0.032 (3)−0.015 (2)−0.003 (2)−0.003 (2)
C200.037 (3)0.045 (3)0.038 (3)−0.018 (3)−0.009 (2)−0.007 (3)
Pt1—O72.020 (4)Pt2—O172.005 (4)
Pt1—S22.1826 (13)Pt2—S42.1850 (14)
Pt1—S12.2495 (15)Pt2—S32.2543 (14)
Pt1—Cl12.3461 (13)Pt2—Cl22.3402 (14)
S1—C11.727 (6)S3—C111.723 (6)
S2—O81.475 (4)S4—O181.477 (4)
S2—C91.767 (6)S4—C201.767 (6)
S2—C101.771 (6)S4—C191.774 (6)
C1—N61.346 (7)C11—N161.353 (7)
C1—C21.403 (8)C11—C121.394 (8)
C2—C31.379 (9)C12—C131.368 (9)
C2—H20.95C12—H120.95
C3—C41.394 (10)C13—C141.396 (9)
C3—H30.95C13—H130.95
C4—C51.353 (9)C14—C151.359 (8)
C4—H40.95C14—H140.95
C5—N61.366 (7)C15—N161.366 (7)
C5—H50.95C15—H150.95
N6—O71.358 (6)N16—O171.378 (5)
C9—H9A0.98C19—H19A0.98
C9—H9B0.98C19—H19B0.98
C9—H9C0.98C19—H19C0.98
C10—H10A0.98C20—H20A0.98
C10—H10B0.98C20—H20B0.98
C10—H10C0.98C20—H20C0.98
O7—Pt1—S2179.05 (12)O17—Pt2—S4179.35 (11)
O7—Pt1—S186.29 (11)O17—Pt2—S386.41 (11)
S2—Pt1—S193.15 (5)S4—Pt2—S394.02 (5)
O7—Pt1—Cl189.02 (11)O17—Pt2—Cl287.69 (11)
S2—Pt1—Cl191.57 (5)S4—Pt2—Cl291.89 (5)
S1—Pt1—Cl1174.53 (5)S3—Pt2—Cl2174.07 (5)
C1—S1—Pt197.4 (2)C11—S3—Pt297.42 (19)
O8—S2—C9107.7 (3)O18—S4—C20108.9 (3)
O8—S2—C10108.1 (3)O18—S4—C19108.9 (3)
C9—S2—C10101.3 (3)C20—S4—C19101.1 (3)
O8—S2—Pt1116.54 (17)O18—S4—Pt2117.14 (19)
C9—S2—Pt1111.3 (2)C20—S4—Pt2110.2 (2)
C10—S2—Pt1110.8 (2)C19—S4—Pt2109.4 (2)
N6—C1—C2117.9 (5)N16—C11—C12117.2 (5)
N6—C1—S1119.2 (4)N16—C11—S3119.3 (4)
C2—C1—S1122.9 (5)C12—C11—S3123.5 (4)
C3—C2—C1119.9 (6)C13—C12—C11121.3 (6)
C3—C2—H2120.1C13—C12—H12119.4
C1—C2—H2120.1C11—C12—H12119.4
C2—C3—C4119.9 (6)C12—C13—C14119.2 (5)
C2—C3—H3120.0C12—C13—H13120.4
C4—C3—H3120.0C14—C13—H13120.4
C5—C4—C3119.4 (6)C15—C14—C13119.8 (6)
C5—C4—H4120.3C15—C14—H14120.1
C3—C4—H4120.3C13—C14—H14120.1
C4—C5—N6120.0 (6)C14—C15—N16119.4 (5)
C4—C5—H5120.0C14—C15—H15120.3
N6—C5—H5120.0N16—C15—H15120.3
C1—N6—O7121.7 (4)C11—N16—C15123.0 (5)
C1—N6—C5122.9 (5)C11—N16—O17120.9 (4)
O7—N6—C5115.4 (5)C15—N16—O17116.0 (4)
N6—O7—Pt1115.3 (3)N16—O17—Pt2115.4 (3)
S2—C9—H9A109.5S4—C19—H19A109.5
S2—C9—H9B109.5S4—C19—H19B109.5
H9A—C9—H9B109.5H19A—C19—H19B109.5
S2—C9—H9C109.5S4—C19—H19C109.5
H9A—C9—H9C109.5H19A—C19—H19C109.5
H9B—C9—H9C109.5H19B—C19—H19C109.5
S2—C10—H10A109.5S4—C20—H20A109.5
S2—C10—H10B109.5S4—C20—H20B109.5
H10A—C10—H10B109.5H20A—C20—H20B109.5
S2—C10—H10C109.5S4—C20—H20C109.5
H10A—C10—H10C109.5H20A—C20—H20C109.5
H10B—C10—H10C109.5H20B—C20—H20C109.5
O7—Pt1—S1—C1−0.8 (2)O17—Pt2—S3—C11−5.7 (2)
S2—Pt1—S1—C1180.0 (2)S4—Pt2—S3—C11174.82 (19)
S1—Pt1—S2—O812.4 (2)S3—Pt2—S4—O18−5.8 (2)
Cl1—Pt1—S2—O8−170.4 (2)Cl2—Pt2—S4—O18173.6 (2)
S1—Pt1—S2—C9136.5 (2)S3—Pt2—S4—C20−131.0 (2)
Cl1—Pt1—S2—C9−46.3 (2)Cl2—Pt2—S4—C2048.5 (2)
S1—Pt1—S2—C10−111.7 (2)S3—Pt2—S4—C19118.7 (2)
Cl1—Pt1—S2—C1065.5 (2)Cl2—Pt2—S4—C19−61.8 (2)
Pt1—S1—C1—N61.1 (5)Pt2—S3—C11—N164.8 (4)
Pt1—S1—C1—C2−179.1 (5)Pt2—S3—C11—C12−174.0 (5)
N6—C1—C2—C30.9 (9)N16—C11—C12—C13−0.1 (8)
S1—C1—C2—C3−178.9 (5)S3—C11—C12—C13178.7 (5)
C1—C2—C3—C4−0.8 (10)C11—C12—C13—C140.5 (9)
C2—C3—C4—C50.4 (10)C12—C13—C14—C15−0.5 (9)
C3—C4—C5—N6−0.1 (9)C13—C14—C15—N160.2 (9)
C2—C1—N6—O7179.4 (5)C12—C11—N16—C15−0.3 (8)
S1—C1—N6—O7−0.9 (7)S3—C11—N16—C15−179.1 (4)
C2—C1—N6—C5−0.7 (8)C12—C11—N16—O17178.9 (5)
S1—C1—N6—C5179.1 (4)S3—C11—N16—O170.0 (7)
C4—C5—N6—C10.3 (9)C14—C15—N16—C110.2 (8)
C4—C5—N6—O7−179.7 (5)C14—C15—N16—O17−178.9 (5)
C1—N6—O7—Pt10.0 (6)C11—N16—O17—Pt2−5.9 (6)
C5—N6—O7—Pt1−180.0 (4)C15—N16—O17—Pt2173.3 (4)
S1—Pt1—O7—N60.6 (3)S3—Pt2—O17—N167.0 (3)
Cl1—Pt1—O7—N6−176.6 (3)Cl2—Pt2—O17—N16−172.5 (3)
D—H···AD—HH···AD···AD—H···A
C9—H9A···O17i0.982.433.351 (8)157
C9—H9B···Cl10.982.733.350 (6)121
C10—H10A···Cl1ii0.982.733.601 (7)149
C13—H13···O7iii0.952.373.268 (8)158
C15—H15···O8iv0.952.393.271 (7)155
C19—H19A···O8v0.982.543.456 (7)155
C20—H20A···O18vi0.982.493.460 (8)172
C20—H20B···Cl20.982.753.366 (7)122
Pt1—O72.020 (4)
Pt1—S22.1826 (13)
Pt1—S12.2495 (15)
Pt1—Cl12.3461 (13)
Pt2—O172.005 (4)
Pt2—S42.1850 (14)
Pt2—S32.2543 (14)
Pt2—Cl22.3402 (14)
O7—Pt1—S2179.05 (12)
O7—Pt1—S186.29 (11)
S2—Pt1—S193.15 (5)
O7—Pt1—Cl189.02 (11)
S2—Pt1—Cl191.57 (5)
S1—Pt1—Cl1174.53 (5)
O17—Pt2—S4179.35 (11)
O17—Pt2—S386.41 (11)
S4—Pt2—S394.02 (5)
O17—Pt2—Cl287.69 (11)
S4—Pt2—Cl291.89 (5)
S3—Pt2—Cl2174.07 (5)
Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯AD—HH⋯AD⋯AD—H⋯A
C9—H9A⋯O17i0.982.433.351 (8)157
C9—H9B⋯Cl10.982.733.350 (6)121
C10—H10A⋯Cl1ii0.982.733.601 (7)149
C13—H13⋯O7iii0.952.373.268 (8)158
C15—H15⋯O8iv0.952.393.271 (7)155
C19—H19A⋯O8v0.982.543.456 (7)155
C20—H20A⋯O18vi0.982.493.460 (8)172
C20—H20B⋯Cl20.982.753.366 (7)122

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) ; (vi) .

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