Bis[μ-4-methyl-2-(2-pyridyl­methyl­sulfan­yl)pyrimidine-κN1]bis­[(trifluoro­methanesulfonato-κO)silver(I)]

Wang, H.-H.; Zhang, C.-Y.; Cui, Y.; Gao, Q.; Xie, Y.-B.

doi:10.1107/S1600536810043631

metal-organic compounds

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ISSN: 2056-9890

Volume 66| Part 11| November 2010| Page m1496

https://doi.org/10.1107/S1600536810043631

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Bis[μ-4-methyl-2-(2-pyridylmethylsulfanyl)pyrimidine-κN¹]bis[(trifluoromethanesulfonato-κO)silver(I)]

Huan-Huan Wang,^a Chao-Yan Zhang,^a Yue Cui,^a Qian Gao ^a and Ya-Bo Xie ^a ^*

^aCollege of Environmental and Energy Engineering, Beijing University of Technology, Beijing 100124, People's Republic of China
^*Correspondence e-mail: xieyabo@bjut.edu.cn

(Received 18 October 2010; accepted 26 October 2010; online 31 October 2010)

In the centrosymmetric dinuclear title complex, [Ag₂(CF₃SO₃)₂(C₁₁H₁₁N₃S)₂], the Ag^I 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 ). For a related structure, see: Xie et al. (2006 ).

Experimental

Crystal data

[Ag₂(CF₃O₃S)₂(C₁₁H₁₁N₃S)₂]
M_r = 948.50
Triclinic, $[P \overline 1]$
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 ) 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[F² > 2σ(F²)] = 0.044
wR(F²) = 0.138
S = 0.97
3681 reflections
217 parameters
H-atom parameters constrained
Δρ_max = 0.72 e Å⁻³
Δρ_min = −0.41 e Å⁻³

Table 1
Selected bond lengths (Å)

Ag1—N1	2.150 (4)
Ag1—N3ⁱ	2.161 (3)
Ag1—O5	2.700 (4)
Symmetry code: (i) -x+1, -y+1, -z.

Data collection: SMART (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; 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.

Supporting information

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

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810043631/hy2366Isup2.hkl

checkCIF report

Comment top

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 Ag^I 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.

Related literature top

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

Experimental top

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.

Structure description top

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

Computing details top

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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 (Sheldrick, 2008).

Figures top

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.]

Bis[µ-4-methyl-2-(2-pyridylmethylsulfanyl)pyrimidine- κN¹]bis[(trifluoromethanesulfonato-κO)silver(I)] top

Crystal data top

[Ag₂(CF₃O₃S)₂(C₁₁H₁₁N₃S)₂]	Z = 1
M_r = 948.50	F(000) = 468
Triclinic, P1	D_x = 1.953 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.9999 (18) Å	Cell parameters from 3696 reflections
b = 9.1087 (18) Å	θ = 3.1–27.5°
c = 10.937 (2) Å	µ = 1.56 mm⁻¹
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 top

Bruker APEX CCD diffractometer	3681 independent reflections
Radiation source: fine-focus sealed tube	3007 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.028
φ and ω scans	θ_max = 27.5°, θ_min = 3.1°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −11→11
T_min = 0.800, T_max = 0.860	k = −11→11
8621 measured reflections	l = −14→14

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.138	H-atom parameters constrained
S = 0.97	w = 1/[σ²(F_o²) + (0.1P)²] where P = (F_o² + 2F_c²)/3
3681 reflections	(Δ/σ)_max = 0.001
217 parameters	Δρ_max = 0.72 e Å⁻³
0 restraints	Δρ_min = −0.41 e Å⁻³

Crystal data top

[Ag₂(CF₃O₃S)₂(C₁₁H₁₁N₃S)₂]	γ = 68.97 (3)°
M_r = 948.50	V = 806.3 (3) Å³
Triclinic, P1	Z = 1
a = 8.9999 (18) Å	Mo Kα radiation
b = 9.1087 (18) Å	µ = 1.56 mm⁻¹
c = 10.937 (2) Å	T = 293 K
α = 75.07 (3)°	0.15 × 0.12 × 0.10 mm
β = 88.59 (3)°

Data collection top

Bruker APEX CCD diffractometer	3681 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	3007 reflections with I > 2σ(I)
T_min = 0.800, T_max = 0.860	R_int = 0.028
8621 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	0 restraints
wR(F²) = 0.138	H-atom parameters constrained
S = 0.97	Δρ_max = 0.72 e Å⁻³
3681 reflections	Δρ_min = −0.41 e Å⁻³
217 parameters

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

	x	y	z	U_iso*/U_eq
Ag1	0.76401 (4)	0.50847 (4)	0.08737 (3)	0.04428 (16)
S1	0.60205 (13)	0.26916 (13)	0.01310 (10)	0.0376 (3)
N1	0.7984 (4)	0.2971 (4)	0.2435 (3)	0.0379 (8)
N2	0.5373 (4)	0.0216 (4)	0.1602 (3)	0.0348 (7)
N3	0.3225 (4)	0.2503 (4)	0.0425 (3)	0.0318 (7)
C1	0.8050 (6)	0.3150 (6)	0.3602 (4)	0.0463 (11)
H1A	0.8072	0.4131	0.3690	0.056*
C2	0.8086 (6)	0.1969 (6)	0.4671 (5)	0.0526 (12)
H2A	0.8122	0.2143	0.5470	0.063*
C3	0.8067 (7)	0.0511 (6)	0.4541 (5)	0.0540 (12)
H3A	0.8082	−0.0316	0.5253	0.065*
C4	0.8026 (5)	0.0294 (5)	0.3361 (5)	0.0440 (10)
H4A	0.8026	−0.0689	0.3261	0.053*
C5	0.7986 (5)	0.1535 (5)	0.2314 (4)	0.0340 (8)
C6	0.7891 (5)	0.1365 (5)	0.1003 (4)	0.0357 (9)
H6A	0.8038	0.0243	0.1048	0.043*
H6B	0.8751	0.1606	0.0551	0.043*
C7	0.4768 (5)	0.1670 (5)	0.0809 (4)	0.0314 (8)
C8	0.4366 (5)	−0.0528 (5)	0.2077 (4)	0.0374 (9)
C9	0.2748 (5)	0.0237 (5)	0.1742 (5)	0.0420 (10)
H9A	0.2036	−0.0269	0.2068	0.050*
C10	0.2224 (5)	0.1756 (5)	0.0921 (5)	0.0420 (10)
H10A	0.1136	0.2291	0.0697	0.050*
C11	0.5077 (6)	−0.2182 (6)	0.2968 (5)	0.0533 (12)
H11A	0.6214	−0.2489	0.3064	0.080*
H11B	0.4831	−0.2954	0.2638	0.080*
H11C	0.4645	−0.2171	0.3779	0.080*
S4	0.93636 (13)	0.38405 (13)	−0.22242 (10)	0.0377 (3)
F4	0.6405 (4)	0.5740 (6)	−0.2672 (5)	0.1020 (14)
F5	0.7551 (7)	0.5239 (5)	−0.4298 (4)	0.130 (2)
F6	0.8009 (6)	0.6879 (4)	−0.3447 (5)	0.1096 (16)
O4	0.8891 (5)	0.2489 (4)	−0.2085 (4)	0.0680 (11)
O5	0.9355 (5)	0.4366 (5)	−0.1096 (3)	0.0722 (12)
O6	1.0735 (5)	0.3760 (5)	−0.2887 (5)	0.0839 (15)
C24	0.7756 (8)	0.5505 (7)	−0.3235 (5)	0.0635 (15)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ag1	0.0506 (2)	0.0315 (2)	0.0441 (2)	−0.01457 (15)	−0.00205 (16)	0.00090 (15)
S1	0.0406 (6)	0.0352 (5)	0.0372 (6)	−0.0193 (4)	0.0008 (4)	−0.0018 (4)
N1	0.0400 (19)	0.0379 (19)	0.0376 (19)	−0.0195 (16)	0.0016 (15)	−0.0051 (15)
N2	0.0354 (17)	0.0285 (16)	0.0391 (19)	−0.0131 (14)	−0.0017 (15)	−0.0044 (14)
N3	0.0337 (17)	0.0267 (16)	0.0347 (17)	−0.0119 (13)	0.0004 (14)	−0.0065 (13)
C1	0.062 (3)	0.041 (2)	0.044 (3)	−0.028 (2)	0.003 (2)	−0.011 (2)
C2	0.067 (3)	0.052 (3)	0.044 (3)	−0.029 (2)	−0.001 (2)	−0.011 (2)
C3	0.076 (3)	0.044 (3)	0.040 (3)	−0.030 (3)	−0.001 (2)	0.005 (2)
C4	0.045 (2)	0.033 (2)	0.055 (3)	−0.0189 (19)	−0.004 (2)	−0.006 (2)
C5	0.0302 (19)	0.0310 (19)	0.039 (2)	−0.0112 (16)	0.0035 (17)	−0.0058 (17)
C6	0.030 (2)	0.036 (2)	0.043 (2)	−0.0138 (16)	0.0022 (17)	−0.0113 (18)
C7	0.035 (2)	0.0287 (19)	0.033 (2)	−0.0123 (16)	0.0003 (16)	−0.0118 (16)
C8	0.048 (2)	0.0286 (19)	0.038 (2)	−0.0159 (18)	0.0007 (19)	−0.0090 (17)
C9	0.041 (2)	0.037 (2)	0.052 (3)	−0.0249 (19)	0.001 (2)	−0.004 (2)
C10	0.030 (2)	0.038 (2)	0.055 (3)	−0.0130 (17)	−0.0072 (19)	−0.007 (2)
C11	0.053 (3)	0.040 (2)	0.059 (3)	−0.019 (2)	−0.002 (2)	0.003 (2)
S4	0.0418 (6)	0.0342 (5)	0.0405 (6)	−0.0173 (4)	0.0089 (5)	−0.0110 (4)
F4	0.053 (2)	0.114 (3)	0.111 (3)	0.003 (2)	−0.013 (2)	−0.029 (3)
F5	0.206 (6)	0.096 (3)	0.053 (2)	−0.003 (4)	−0.048 (3)	−0.029 (2)
F6	0.160 (4)	0.0394 (19)	0.110 (3)	−0.030 (2)	−0.016 (3)	0.005 (2)
O4	0.073 (3)	0.0426 (19)	0.096 (3)	−0.0370 (19)	0.015 (2)	−0.009 (2)
O5	0.079 (3)	0.071 (3)	0.050 (2)	0.002 (2)	−0.015 (2)	−0.029 (2)
O6	0.072 (3)	0.068 (3)	0.121 (4)	−0.036 (2)	0.055 (3)	−0.030 (3)
C24	0.092 (4)	0.046 (3)	0.040 (3)	−0.010 (3)	−0.010 (3)	−0.011 (2)

Geometric parameters (Å, º) top

Ag1—N1	2.150 (4)	C4—H4A	0.9300
Ag1—N3ⁱ	2.161 (3)	C5—C6	1.488 (6)
Ag1—O5	2.700 (4)	C6—H6A	0.9700
S1—C7	1.744 (4)	C6—H6B	0.9700
S1—C6	1.797 (4)	C8—C9	1.381 (6)
N1—C1	1.333 (6)	C8—C11	1.488 (6)
N1—C5	1.347 (5)	C9—C10	1.362 (6)
N2—C7	1.311 (5)	C9—H9A	0.9300
N2—C8	1.337 (5)	C10—H10A	0.9300
N3—C7	1.337 (5)	C11—H11A	0.9600
N3—C10	1.340 (5)	C11—H11B	0.9600
N3—Ag1ⁱ	2.161 (3)	C11—H11C	0.9600
C1—C2	1.362 (7)	S4—O6	1.404 (4)
C1—H1A	0.9300	S4—O4	1.412 (3)
C2—C3	1.378 (7)	S4—O5	1.433 (4)
C2—H2A	0.9300	S4—C24	1.804 (6)
C3—C4	1.358 (7)	F4—C24	1.323 (8)
C3—H3A	0.9300	F5—C24	1.278 (6)
C4—C5	1.377 (6)	F6—C24	1.313 (7)

N1—Ag1—N3ⁱ	164.97 (13)	N2—C7—N3	126.4 (4)
N1—Ag1—O5	112.81 (13)	N2—C7—S1	119.9 (3)
N3ⁱ—Ag1—O5	81.84 (13)	N3—C7—S1	113.7 (3)
C7—S1—C6	100.93 (19)	N2—C8—C9	120.3 (4)
C1—N1—C5	118.1 (4)	N2—C8—C11	116.8 (4)
C1—N1—Ag1	117.2 (3)	C9—C8—C11	122.9 (4)
C5—N1—Ag1	124.4 (3)	C10—C9—C8	118.0 (4)
C7—N2—C8	117.6 (3)	C10—C9—H9A	121.0
C7—N3—C10	115.5 (3)	C8—C9—H9A	121.0
C7—N3—Ag1ⁱ	123.1 (3)	N3—C10—C9	122.2 (4)
C10—N3—Ag1ⁱ	121.4 (3)	N3—C10—H10A	118.9
N1—C1—C2	123.3 (4)	C9—C10—H10A	118.9
N1—C1—H1A	118.4	C8—C11—H11A	109.5
C2—C1—H1A	118.4	C8—C11—H11B	109.5
C1—C2—C3	118.3 (5)	H11A—C11—H11B	109.5
C1—C2—H2A	120.8	C8—C11—H11C	109.5
C3—C2—H2A	120.8	H11A—C11—H11C	109.5
C4—C3—C2	119.3 (5)	H11B—C11—H11C	109.5
C4—C3—H3A	120.4	O6—S4—O4	115.1 (3)
C2—C3—H3A	120.4	O6—S4—O5	113.5 (3)
C3—C4—C5	119.8 (4)	O4—S4—O5	115.0 (3)
C3—C4—H4A	120.1	O6—S4—C24	105.0 (3)
C5—C4—H4A	120.1	O4—S4—C24	103.5 (3)
N1—C5—C4	121.2 (4)	O5—S4—C24	102.9 (2)
N1—C5—C6	117.4 (4)	S4—O5—Ag1	144.3 (3)
C4—C5—C6	121.4 (4)	F5—C24—F6	108.9 (5)
C5—C6—S1	112.7 (3)	F5—C24—F4	108.0 (6)
C5—C6—H6A	109.0	F6—C24—F4	106.2 (5)
S1—C6—H6A	109.0	F5—C24—S4	112.2 (4)
C5—C6—H6B	109.0	F6—C24—S4	111.1 (5)
S1—C6—H6B	109.0	F4—C24—S4	110.1 (4)
H6A—C6—H6B	107.8

N3ⁱ—Ag1—N1—C1	−51.9 (6)	C6—S1—C7—N2	−7.9 (4)
O5—Ag1—N1—C1	141.6 (3)	C6—S1—C7—N3	172.8 (3)
N3ⁱ—Ag1—N1—C5	121.5 (5)	C7—N2—C8—C9	−0.7 (6)
O5—Ag1—N1—C5	−45.0 (4)	C7—N2—C8—C11	179.6 (4)
C5—N1—C1—C2	−1.4 (7)	N2—C8—C9—C10	0.1 (7)
Ag1—N1—C1—C2	172.5 (4)	C11—C8—C9—C10	179.8 (4)
N1—C1—C2—C3	0.6 (8)	C7—N3—C10—C9	−1.2 (6)
C1—C2—C3—C4	0.5 (8)	Ag1ⁱ—N3—C10—C9	−179.9 (4)
C2—C3—C4—C5	−0.8 (8)	C8—C9—C10—N3	0.9 (7)
C1—N1—C5—C4	1.1 (6)	O6—S4—O5—Ag1	177.9 (4)
Ag1—N1—C5—C4	−172.3 (3)	O4—S4—O5—Ag1	−46.7 (5)
C1—N1—C5—C6	179.2 (4)	C24—S4—O5—Ag1	65.0 (5)
Ag1—N1—C5—C6	5.8 (5)	N1—Ag1—O5—S4	85.8 (4)
C3—C4—C5—N1	0.0 (7)	N3ⁱ—Ag1—O5—S4	−90.7 (4)
C3—C4—C5—C6	−178.1 (4)	O6—S4—C24—F5	62.5 (6)
N1—C5—C6—S1	−65.9 (4)	O4—S4—C24—F5	−58.5 (6)
C4—C5—C6—S1	112.3 (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—N3	0.5 (6)	O4—S4—C24—F6	179.3 (4)
C8—N2—C7—S1	−178.8 (3)	O5—S4—C24—F6	59.2 (5)
C10—N3—C7—N2	0.5 (6)	O6—S4—C24—F4	−177.1 (4)
Ag1ⁱ—N3—C7—N2	179.2 (3)	O4—S4—C24—F4	61.8 (4)
C10—N3—C7—S1	179.7 (3)	O5—S4—C24—F4	−58.2 (5)
Ag1ⁱ—N3—C7—S1	−1.6 (4)

Symmetry code: (i) −x+1, −y+1, −z.

Experimental details

Crystal data
Chemical formula	[Ag₂(CF₃O₃S)₂(C₁₁H₁₁N₃S)₂]
M_r	948.50
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	8.9999 (18), 9.1087 (18), 10.937 (2)
α, β, γ (°)	75.07 (3), 88.59 (3), 68.97 (3)
V (Å³)	806.3 (3)
Z	1
Radiation type	Mo Kα
µ (mm⁻¹)	1.56
Crystal size (mm)	0.15 × 0.12 × 0.10

Data collection
Diffractometer	Bruker APEX CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.800, 0.860
No. of measured, independent and observed [I > 2σ(I)] reflections	8621, 3681, 3007
R_int	0.028
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.138, 0.97
No. of reflections	3681
No. of parameters	217
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.72, −0.41

Computer programs: SMART (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected bond lengths (Å) top

Ag1—N1	2.150 (4)	Ag1—O5	2.700 (4)
Ag1—N3ⁱ	2.161 (3)

Symmetry code: (i) −x+1, −y+1, −z.

Acknowledgements

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).

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