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Acta Crystallogr Sect E Struct Rep Online. 2010 November 1; 66(Pt 11): m1496.
Published online 2010 October 31. doi:  10.1107/S1600536810043631
PMCID: PMC3009204

Bis[μ-4-methyl-2-(2-pyridyl­methyl­sulfan­yl)pyrimidine-κN 1]bis­[(trifluoro­methanesulfonato-κO)silver(I)]

Abstract

In the centrosymmetric dinuclear title complex, [Ag2(CF3SO3)2(C11H11N3S)2], the AgI atom is coordinated by two N atoms from two 4-methyl-2-(2-pyridyl­methyl­sulfan­yl)pyrimidine ligands and one O atom from a trifluoro­methane­sulfonate anion in a distorted T-type coordination geometry. The ligand adopts a bidentate bridging coordination mode through one pyridyl N atom and one pyrimidine N atom. In the crystal structure, π–π inter­actions are present between adjacent pyrimidine rings, with a centroid-to-centroid distance of 3.875 (7) Å.

Related literature

For the architectures of metal complexes, see: Hamblin et al. (2002 [triangle]). For a related structure, see: Xie et al. (2006 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-m1496-scheme1.jpg

Experimental

Crystal data

  • [Ag2(CF3O3S)2(C11H11N3S)2]
  • M r = 948.50
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-m1496-efi1.jpg
  • a = 8.9999 (18) Å
  • b = 9.1087 (18) Å
  • c = 10.937 (2) Å
  • α = 75.07 (3)°
  • β = 88.59 (3)°
  • γ = 68.97 (3)°
  • V = 806.3 (3) Å3
  • Z = 1
  • Mo Kα radiation
  • μ = 1.56 mm−1
  • T = 293 K
  • 0.15 × 0.12 × 0.10 mm

Data collection

  • Bruker APEX CCD diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2001 [triangle]) T min = 0.800, T max = 0.860
  • 8621 measured reflections
  • 3681 independent reflections
  • 3007 reflections with I > 2σ(I)
  • R int = 0.028

Refinement

  • R[F 2 > 2σ(F 2)] = 0.044
  • wR(F 2) = 0.138
  • S = 0.97
  • 3681 reflections
  • 217 parameters
  • H-atom parameters constrained
  • Δρmax = 0.72 e Å−3
  • Δρmin = −0.41 e Å−3

Data collection: SMART (Bruker, 2007 [triangle]); cell refinement: SAINT (Bruker, 2007 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Selected bond lengths (Å)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810043631/hy2366sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810043631/hy2366Isup2.hkl

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

Acknowledgments

This work was supported by the Eighth Technology Fund for Postgraduates of Beijing University of Technology (grant No. ykj-2010-3399), the National Natural Science Foundation of China (grant No. 21075114), the Science and Technology Development Project of Beijing Education Committee (grant No. KM200910005025) and the Special Environmental Protection Fund for Public Welfare (project No. 201009015).

supplementary crystallographic information

Comment

The coordination geometry of metal ions and the nature of ligands decide the generation of coordination architectures (Hamblin et al., 2002). In previous studies, much attention has been paid to the use of flexible bridging ligands because of their conformational freedom and flexible properties (Xie et al., 2006). As part of our investigation of flexible ligands and their complexes, the crystal structure of a silver(I) complex with a flexible thioether ligand, the title compound, is reported here.

In the binuclear structure of the title complex (Fig. 1), the AgI atom is coordinated by two N atoms from two 4-methyl-2-(2-pyridylmethylsulfanyl)pyrimidine ligands and one O atom from a trifluoromethanesulfonate anion (Table 1), displaying a slightly distorted T-type coordination geometry. The ligand adopts a bidentate bridging coordination mode through two N atoms. The dihedral angle between the pyrimidine ring and pyridine ring is 82.67 (3)°. The two pyrimidine rings are nearly parallel, and so are the two pyridine rings. In the crystal structure, π–π interactions between adjacent pyrimidine rings are present, with a centroid–centroid distance of 3.875 (7) Å.

Experimental

A solution of AgSO3CF3 (0.04 mmol) in acetone (4 ml) was carefully layered on top of a mixture of chloroform (2 ml) and acetone (2 ml), which was carefully layered on top of a solution of 4-methyl-2-(2-pyridylmethylsulfanyl)pyrimidine (0.04 mmol) in chloroform (4 ml) in a test tube. After 2 weeks at room temperature, colourless prism single crystals appeared.

Refinement

All H atoms were positioned geometrically and refined as riding, with C—H = 0.93–0.97 Å and Uiso(H) = 1.2(1.5 for methyl)Ueq(C).

Figures

Fig. 1.
The molecular structure of the title compound, with displacement ellipsoids drawn at the 30% probability level. [Symmetry code: (A) -x + 1, -y + 1, -z.]

Crystal data

[Ag2(CF3O3S)2(C11H11N3S)2]Z = 1
Mr = 948.50F(000) = 468
Triclinic, P1Dx = 1.953 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.9999 (18) ÅCell parameters from 3696 reflections
b = 9.1087 (18) Åθ = 3.1–27.5°
c = 10.937 (2) ŵ = 1.56 mm1
α = 75.07 (3)°T = 293 K
β = 88.59 (3)°Prism, colourless
γ = 68.97 (3)°0.15 × 0.12 × 0.10 mm
V = 806.3 (3) Å3

Data collection

Bruker APEX CCD diffractometer3681 independent reflections
Radiation source: fine-focus sealed tube3007 reflections with I > 2σ(I)
graphiteRint = 0.028
[var phi] and ω scansθmax = 27.5°, θmin = 3.1°
Absorption correction: multi-scan (SADABS; Bruker, 2001)h = −11→11
Tmin = 0.800, Tmax = 0.860k = −11→11
8621 measured reflectionsl = −14→14

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)] = 0.044Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.138H-atom parameters constrained
S = 0.97w = 1/[σ2(Fo2) + (0.1P)2] where P = (Fo2 + 2Fc2)/3
3681 reflections(Δ/σ)max = 0.001
217 parametersΔρmax = 0.72 e Å3
0 restraintsΔρmin = −0.41 e Å3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/Ueq
Ag10.76401 (4)0.50847 (4)0.08737 (3)0.04428 (16)
S10.60205 (13)0.26916 (13)0.01310 (10)0.0376 (3)
N10.7984 (4)0.2971 (4)0.2435 (3)0.0379 (8)
N20.5373 (4)0.0216 (4)0.1602 (3)0.0348 (7)
N30.3225 (4)0.2503 (4)0.0425 (3)0.0318 (7)
C10.8050 (6)0.3150 (6)0.3602 (4)0.0463 (11)
H1A0.80720.41310.36900.056*
C20.8086 (6)0.1969 (6)0.4671 (5)0.0526 (12)
H2A0.81220.21430.54700.063*
C30.8067 (7)0.0511 (6)0.4541 (5)0.0540 (12)
H3A0.8082−0.03160.52530.065*
C40.8026 (5)0.0294 (5)0.3361 (5)0.0440 (10)
H4A0.8026−0.06890.32610.053*
C50.7986 (5)0.1535 (5)0.2314 (4)0.0340 (8)
C60.7891 (5)0.1365 (5)0.1003 (4)0.0357 (9)
H6A0.80380.02430.10480.043*
H6B0.87510.16060.05510.043*
C70.4768 (5)0.1670 (5)0.0809 (4)0.0314 (8)
C80.4366 (5)−0.0528 (5)0.2077 (4)0.0374 (9)
C90.2748 (5)0.0237 (5)0.1742 (5)0.0420 (10)
H9A0.2036−0.02690.20680.050*
C100.2224 (5)0.1756 (5)0.0921 (5)0.0420 (10)
H10A0.11360.22910.06970.050*
C110.5077 (6)−0.2182 (6)0.2968 (5)0.0533 (12)
H11A0.6214−0.24890.30640.080*
H11B0.4831−0.29540.26380.080*
H11C0.4645−0.21710.37790.080*
S40.93636 (13)0.38405 (13)−0.22242 (10)0.0377 (3)
F40.6405 (4)0.5740 (6)−0.2672 (5)0.1020 (14)
F50.7551 (7)0.5239 (5)−0.4298 (4)0.130 (2)
F60.8009 (6)0.6879 (4)−0.3447 (5)0.1096 (16)
O40.8891 (5)0.2489 (4)−0.2085 (4)0.0680 (11)
O50.9355 (5)0.4366 (5)−0.1096 (3)0.0722 (12)
O61.0735 (5)0.3760 (5)−0.2887 (5)0.0839 (15)
C240.7756 (8)0.5505 (7)−0.3235 (5)0.0635 (15)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Ag10.0506 (2)0.0315 (2)0.0441 (2)−0.01457 (15)−0.00205 (16)0.00090 (15)
S10.0406 (6)0.0352 (5)0.0372 (6)−0.0193 (4)0.0008 (4)−0.0018 (4)
N10.0400 (19)0.0379 (19)0.0376 (19)−0.0195 (16)0.0016 (15)−0.0051 (15)
N20.0354 (17)0.0285 (16)0.0391 (19)−0.0131 (14)−0.0017 (15)−0.0044 (14)
N30.0337 (17)0.0267 (16)0.0347 (17)−0.0119 (13)0.0004 (14)−0.0065 (13)
C10.062 (3)0.041 (2)0.044 (3)−0.028 (2)0.003 (2)−0.011 (2)
C20.067 (3)0.052 (3)0.044 (3)−0.029 (2)−0.001 (2)−0.011 (2)
C30.076 (3)0.044 (3)0.040 (3)−0.030 (3)−0.001 (2)0.005 (2)
C40.045 (2)0.033 (2)0.055 (3)−0.0189 (19)−0.004 (2)−0.006 (2)
C50.0302 (19)0.0310 (19)0.039 (2)−0.0112 (16)0.0035 (17)−0.0058 (17)
C60.030 (2)0.036 (2)0.043 (2)−0.0138 (16)0.0022 (17)−0.0113 (18)
C70.035 (2)0.0287 (19)0.033 (2)−0.0123 (16)0.0003 (16)−0.0118 (16)
C80.048 (2)0.0286 (19)0.038 (2)−0.0159 (18)0.0007 (19)−0.0090 (17)
C90.041 (2)0.037 (2)0.052 (3)−0.0249 (19)0.001 (2)−0.004 (2)
C100.030 (2)0.038 (2)0.055 (3)−0.0130 (17)−0.0072 (19)−0.007 (2)
C110.053 (3)0.040 (2)0.059 (3)−0.019 (2)−0.002 (2)0.003 (2)
S40.0418 (6)0.0342 (5)0.0405 (6)−0.0173 (4)0.0089 (5)−0.0110 (4)
F40.053 (2)0.114 (3)0.111 (3)0.003 (2)−0.013 (2)−0.029 (3)
F50.206 (6)0.096 (3)0.053 (2)−0.003 (4)−0.048 (3)−0.029 (2)
F60.160 (4)0.0394 (19)0.110 (3)−0.030 (2)−0.016 (3)0.005 (2)
O40.073 (3)0.0426 (19)0.096 (3)−0.0370 (19)0.015 (2)−0.009 (2)
O50.079 (3)0.071 (3)0.050 (2)0.002 (2)−0.015 (2)−0.029 (2)
O60.072 (3)0.068 (3)0.121 (4)−0.036 (2)0.055 (3)−0.030 (3)
C240.092 (4)0.046 (3)0.040 (3)−0.010 (3)−0.010 (3)−0.011 (2)

Geometric parameters (Å, °)

Ag1—N12.150 (4)C4—H4A0.9300
Ag1—N3i2.161 (3)C5—C61.488 (6)
Ag1—O52.700 (4)C6—H6A0.9700
S1—C71.744 (4)C6—H6B0.9700
S1—C61.797 (4)C8—C91.381 (6)
N1—C11.333 (6)C8—C111.488 (6)
N1—C51.347 (5)C9—C101.362 (6)
N2—C71.311 (5)C9—H9A0.9300
N2—C81.337 (5)C10—H10A0.9300
N3—C71.337 (5)C11—H11A0.9600
N3—C101.340 (5)C11—H11B0.9600
N3—Ag1i2.161 (3)C11—H11C0.9600
C1—C21.362 (7)S4—O61.404 (4)
C1—H1A0.9300S4—O41.412 (3)
C2—C31.378 (7)S4—O51.433 (4)
C2—H2A0.9300S4—C241.804 (6)
C3—C41.358 (7)F4—C241.323 (8)
C3—H3A0.9300F5—C241.278 (6)
C4—C51.377 (6)F6—C241.313 (7)
N1—Ag1—N3i164.97 (13)N2—C7—N3126.4 (4)
N1—Ag1—O5112.81 (13)N2—C7—S1119.9 (3)
N3i—Ag1—O581.84 (13)N3—C7—S1113.7 (3)
C7—S1—C6100.93 (19)N2—C8—C9120.3 (4)
C1—N1—C5118.1 (4)N2—C8—C11116.8 (4)
C1—N1—Ag1117.2 (3)C9—C8—C11122.9 (4)
C5—N1—Ag1124.4 (3)C10—C9—C8118.0 (4)
C7—N2—C8117.6 (3)C10—C9—H9A121.0
C7—N3—C10115.5 (3)C8—C9—H9A121.0
C7—N3—Ag1i123.1 (3)N3—C10—C9122.2 (4)
C10—N3—Ag1i121.4 (3)N3—C10—H10A118.9
N1—C1—C2123.3 (4)C9—C10—H10A118.9
N1—C1—H1A118.4C8—C11—H11A109.5
C2—C1—H1A118.4C8—C11—H11B109.5
C1—C2—C3118.3 (5)H11A—C11—H11B109.5
C1—C2—H2A120.8C8—C11—H11C109.5
C3—C2—H2A120.8H11A—C11—H11C109.5
C4—C3—C2119.3 (5)H11B—C11—H11C109.5
C4—C3—H3A120.4O6—S4—O4115.1 (3)
C2—C3—H3A120.4O6—S4—O5113.5 (3)
C3—C4—C5119.8 (4)O4—S4—O5115.0 (3)
C3—C4—H4A120.1O6—S4—C24105.0 (3)
C5—C4—H4A120.1O4—S4—C24103.5 (3)
N1—C5—C4121.2 (4)O5—S4—C24102.9 (2)
N1—C5—C6117.4 (4)S4—O5—Ag1144.3 (3)
C4—C5—C6121.4 (4)F5—C24—F6108.9 (5)
C5—C6—S1112.7 (3)F5—C24—F4108.0 (6)
C5—C6—H6A109.0F6—C24—F4106.2 (5)
S1—C6—H6A109.0F5—C24—S4112.2 (4)
C5—C6—H6B109.0F6—C24—S4111.1 (5)
S1—C6—H6B109.0F4—C24—S4110.1 (4)
H6A—C6—H6B107.8
N3i—Ag1—N1—C1−51.9 (6)C6—S1—C7—N2−7.9 (4)
O5—Ag1—N1—C1141.6 (3)C6—S1—C7—N3172.8 (3)
N3i—Ag1—N1—C5121.5 (5)C7—N2—C8—C9−0.7 (6)
O5—Ag1—N1—C5−45.0 (4)C7—N2—C8—C11179.6 (4)
C5—N1—C1—C2−1.4 (7)N2—C8—C9—C100.1 (7)
Ag1—N1—C1—C2172.5 (4)C11—C8—C9—C10179.8 (4)
N1—C1—C2—C30.6 (8)C7—N3—C10—C9−1.2 (6)
C1—C2—C3—C40.5 (8)Ag1i—N3—C10—C9−179.9 (4)
C2—C3—C4—C5−0.8 (8)C8—C9—C10—N30.9 (7)
C1—N1—C5—C41.1 (6)O6—S4—O5—Ag1177.9 (4)
Ag1—N1—C5—C4−172.3 (3)O4—S4—O5—Ag1−46.7 (5)
C1—N1—C5—C6179.2 (4)C24—S4—O5—Ag165.0 (5)
Ag1—N1—C5—C65.8 (5)N1—Ag1—O5—S485.8 (4)
C3—C4—C5—N10.0 (7)N3i—Ag1—O5—S4−90.7 (4)
C3—C4—C5—C6−178.1 (4)O6—S4—C24—F562.5 (6)
N1—C5—C6—S1−65.9 (4)O4—S4—C24—F5−58.5 (6)
C4—C5—C6—S1112.3 (4)O5—S4—C24—F5−178.5 (5)
C7—S1—C6—C5−76.0 (3)O6—S4—C24—F6−59.7 (5)
C8—N2—C7—N30.5 (6)O4—S4—C24—F6179.3 (4)
C8—N2—C7—S1−178.8 (3)O5—S4—C24—F659.2 (5)
C10—N3—C7—N20.5 (6)O6—S4—C24—F4−177.1 (4)
Ag1i—N3—C7—N2179.2 (3)O4—S4—C24—F461.8 (4)
C10—N3—C7—S1179.7 (3)O5—S4—C24—F4−58.2 (5)
Ag1i—N3—C7—S1−1.6 (4)

Symmetry codes: (i) −x+1, −y+1, −z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HY2366).

References

  • Bruker (2001). SADABS Bruker AXS Inc., Madison, Wisconsin, USA.
  • Bruker (2007). SMART and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Hamblin, J., Childs, L. J., Alcock, N. W. & Hannon, M. J. (2002). J. Chem. Soc. Dalton Trans. pp. 164–169.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Xie, Y.-B., Jiang, L.-Y. & Wang, D. (2006). Acta Cryst. E62, m2479–m2481.

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