metal-organic compounds
Bis(μ-4,6-dimethylpyrimidine-2-thiolato)-κ3N,S:S;κ3S:N,S-bis[(triphenylphosphane-κP)silver(I)]
aDepartment of Chemistry, Faculty of Science, Prince of Songkla University, Hat Yai, Songkhla 90112, Thailand
*Correspondence e-mail: yupa.t@psu.ac.th
The dinuclear title complex, [Ag2(C6H7N2S)2(C18H15P)2], comprises two inversion-related [Ag(C6H7N2S)(C18H15P)] units. The pyrimidinethiolate anion acts both as a bridging and a chelating ligand. The AgI ions are linked via two μ2-S donor atoms, which generate a strictly planar Ag2S2 core with an Ag⋯Ag separation of 2.9569 (4) Å. The AgI ion presents a distorted tetrahedral coordination geometry. In the crystal, weak C—H⋯N and C—H⋯S hydrogen bonds link the complex molecules into a two-dimensional network parallel to (010).
Related literature
For the structures of metal(I) coordination compounds and their potential applications, see: Aslanidis et al. (1997); McFarlane et al. (1998); Nawaz et al. (2011); Hameau et al. (2012); Nimthong et al. (2012); Pakawatchai et al. (2012). For relevant examples of discrete complexes, see: Cox et al. (2000); Lobana et al. (2008); Isab et al. (2010).
Experimental
Crystal data
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Refinement
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Data collection: SMART (Bruker, 1998); cell SAINT (Bruker, 2003); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and publCIF (Westrip, 2010).
Supporting information
10.1107/S1600536812048210/bh2464sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536812048210/bh2464Isup2.hkl
Triphenylphosphane (0.31 g, 1.18 mmol) was dissolved in 30 cm3 of ethanol at 335 K. Silver acetate (0.10 g, 0.60 mmol) was added and the mixture was stirred for 3 h. 4,6-Dimethylpyrimidine-2(1H)-thione (0.18 g, 0.46 mmol) was added and the new reaction mixture was refluxed for 2 h where upon the precipitate gradually disappeared. The resulting clear solution was filtered off and left to evaporate at room temperature. The crystalline solid, which was deposited upon standing for several days, was filtered off and dried under reduced pressure.
The H atoms bonded to C atoms were constrained to ride on their parent atoms with C—H bond lengths of 0.93 Å [aryl CH, Uiso(H) = 1.2Ueq(C)] and 0.96 Å [methyl CH3, Uiso(H) = 1.5Ueq(C)] except for H3, which was located in a difference map and refined isotropically.
Data collection: SMART (Bruker, 1998); cell
SAINT (Bruker, 2003); data reduction: SAINT (Bruker, 2003); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and publCIF (Westrip, 2010).[Ag2(C6H7N2S)2(C18H15P)2] | F(000) = 1032 |
Mr = 1018.67 | Dx = 1.519 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 8845 reflections |
a = 11.7050 (5) Å | θ = 2.2–28.3° |
b = 15.3084 (7) Å | µ = 1.08 mm−1 |
c = 12.5331 (6) Å | T = 293 K |
β = 97.483 (1)° | Block, yellow |
V = 2226.62 (18) Å3 | 0.29 × 0.18 × 0.09 mm |
Z = 2 |
Bruker SMART CCD diffractometer | 5568 independent reflections |
Radiation source: fine-focus sealed tube | 4798 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.023 |
ϕ and ω scans | θmax = 28.3°, θmin = 2.1° |
Absorption correction: multi-scan (SADABS; Bruker, 2003) | h = −15→15 |
Tmin = 0.793, Tmax = 0.909 | k = −20→20 |
26686 measured reflections | l = −16→16 |
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)] = 0.032 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.088 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0481P)2 + 0.8969P] where P = (Fo2 + 2Fc2)/3 |
5568 reflections | (Δ/σ)max = 0.003 |
266 parameters | Δρmax = 0.54 e Å−3 |
0 restraints | Δρmin = −0.29 e Å−3 |
0 constraints |
[Ag2(C6H7N2S)2(C18H15P)2] | V = 2226.62 (18) Å3 |
Mr = 1018.67 | Z = 2 |
Monoclinic, P21/n | Mo Kα radiation |
a = 11.7050 (5) Å | µ = 1.08 mm−1 |
b = 15.3084 (7) Å | T = 293 K |
c = 12.5331 (6) Å | 0.29 × 0.18 × 0.09 mm |
β = 97.483 (1)° |
Bruker SMART CCD diffractometer | 5568 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2003) | 4798 reflections with I > 2σ(I) |
Tmin = 0.793, Tmax = 0.909 | Rint = 0.023 |
26686 measured reflections |
R[F2 > 2σ(F2)] = 0.032 | 0 restraints |
wR(F2) = 0.088 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.04 | Δρmax = 0.54 e Å−3 |
5568 reflections | Δρmin = −0.29 e Å−3 |
266 parameters |
x | y | z | Uiso*/Ueq | ||
C1 | 0.64391 (17) | 0.09032 (14) | −0.12789 (17) | 0.0376 (4) | |
C2 | 0.6887 (2) | 0.20334 (17) | −0.2336 (2) | 0.0512 (6) | |
C3 | 0.6524 (3) | 0.26179 (17) | −0.1622 (2) | 0.0578 (7) | |
C4 | 0.6137 (2) | 0.23054 (15) | −0.07073 (19) | 0.0457 (5) | |
C5 | 0.7338 (4) | 0.2323 (2) | −0.3350 (3) | 0.0798 (10) | |
H5A | 0.7548 | 0.1820 | −0.3739 | 0.120* | |
H5B | 0.8003 | 0.2687 | −0.3168 | 0.120* | |
H5C | 0.6752 | 0.2647 | −0.3790 | 0.120* | |
C6 | 0.5799 (3) | 0.28888 (19) | 0.0155 (2) | 0.0673 (8) | |
H6A | 0.5556 | 0.2540 | 0.0721 | 0.101* | |
H6B | 0.5177 | 0.3261 | −0.0141 | 0.101* | |
H6C | 0.6446 | 0.3241 | 0.0440 | 0.101* | |
C21 | 0.69001 (19) | 0.17384 (14) | 0.30847 (17) | 0.0390 (4) | |
C22 | 0.5829 (2) | 0.21344 (18) | 0.3033 (2) | 0.0525 (6) | |
H22 | 0.5174 | 0.1845 | 0.2712 | 0.063* | |
C23 | 0.5735 (3) | 0.2965 (2) | 0.3463 (2) | 0.0662 (8) | |
H23 | 0.5015 | 0.3229 | 0.3427 | 0.079* | |
C24 | 0.6690 (3) | 0.33977 (17) | 0.3938 (2) | 0.0654 (8) | |
H24 | 0.6618 | 0.3951 | 0.4230 | 0.079* | |
C25 | 0.7747 (3) | 0.30172 (18) | 0.3984 (2) | 0.0620 (7) | |
H25 | 0.8396 | 0.3314 | 0.4304 | 0.074* | |
C26 | 0.7861 (2) | 0.21889 (17) | 0.3557 (2) | 0.0533 (6) | |
H26 | 0.8587 | 0.1936 | 0.3588 | 0.064* | |
C31 | 0.66300 (17) | −0.00663 (15) | 0.36218 (17) | 0.0384 (4) | |
C32 | 0.6224 (2) | −0.08985 (19) | 0.3347 (2) | 0.0581 (6) | |
H32 | 0.6112 | −0.1070 | 0.2630 | 0.070* | |
C33 | 0.5986 (3) | −0.1472 (2) | 0.4139 (3) | 0.0799 (10) | |
H33 | 0.5735 | −0.2035 | 0.3955 | 0.096* | |
C34 | 0.6118 (3) | −0.1213 (3) | 0.5202 (3) | 0.0781 (10) | |
H34 | 0.5955 | −0.1602 | 0.5732 | 0.094* | |
C35 | 0.6487 (3) | −0.0385 (2) | 0.5481 (2) | 0.0698 (9) | |
H35 | 0.6559 | −0.0207 | 0.6196 | 0.084* | |
C36 | 0.6751 (2) | 0.0184 (2) | 0.4697 (2) | 0.0530 (6) | |
H36 | 0.7013 | 0.0743 | 0.4890 | 0.064* | |
N1 | 0.60828 (16) | 0.14406 (12) | −0.05384 (15) | 0.0397 (4) | |
N2 | 0.68507 (17) | 0.11646 (13) | −0.21745 (15) | 0.0452 (4) | |
H3 | 0.665 (3) | 0.318 (2) | −0.173 (2) | 0.064 (8)* | |
C11 | 0.84851 (19) | 0.04687 (14) | 0.2463 (2) | 0.0406 (5) | |
C12 | 0.8906 (3) | 0.0742 (2) | 0.1534 (2) | 0.0591 (7) | |
H12 | 0.8425 | 0.1018 | 0.0987 | 0.071* | |
C13 | 1.0069 (3) | 0.0597 (2) | 0.1432 (3) | 0.0782 (11) | |
H13 | 1.0360 | 0.0783 | 0.0815 | 0.094* | |
C14 | 1.0778 (3) | 0.0188 (2) | 0.2223 (4) | 0.0801 (11) | |
H14 | 1.1547 | 0.0093 | 0.2143 | 0.096* | |
C15 | 1.0368 (2) | −0.0081 (2) | 0.3123 (3) | 0.0726 (9) | |
H15 | 1.0858 | −0.0362 | 0.3658 | 0.087* | |
C16 | 0.9221 (2) | 0.00566 (18) | 0.3264 (2) | 0.0531 (6) | |
H16 | 0.8950 | −0.0127 | 0.3892 | 0.064* | |
Ag1 | 0.570898 (16) | 0.048363 (12) | 0.086830 (13) | 0.04660 (8) | |
P1 | 0.69618 (5) | 0.06407 (4) | 0.25410 (4) | 0.03501 (12) | |
S1 | 0.35819 (5) | 0.02130 (4) | 0.09946 (5) | 0.04512 (14) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0319 (9) | 0.0395 (11) | 0.0411 (11) | 0.0003 (8) | 0.0034 (8) | 0.0072 (9) |
C2 | 0.0592 (15) | 0.0507 (14) | 0.0446 (12) | −0.0067 (11) | 0.0096 (11) | 0.0118 (11) |
C3 | 0.083 (2) | 0.0362 (13) | 0.0531 (15) | −0.0049 (12) | 0.0057 (13) | 0.0099 (11) |
C4 | 0.0538 (13) | 0.0383 (11) | 0.0436 (12) | 0.0023 (10) | 0.0012 (10) | 0.0032 (9) |
C5 | 0.113 (3) | 0.070 (2) | 0.0621 (18) | −0.0094 (19) | 0.0349 (18) | 0.0209 (16) |
C6 | 0.097 (2) | 0.0480 (15) | 0.0575 (16) | 0.0074 (15) | 0.0102 (16) | −0.0049 (12) |
C21 | 0.0473 (11) | 0.0363 (10) | 0.0345 (10) | 0.0001 (9) | 0.0090 (9) | 0.0024 (8) |
C22 | 0.0541 (14) | 0.0543 (14) | 0.0499 (13) | 0.0089 (11) | 0.0103 (11) | 0.0040 (11) |
C23 | 0.082 (2) | 0.0571 (16) | 0.0636 (17) | 0.0293 (16) | 0.0268 (16) | 0.0113 (14) |
C24 | 0.108 (2) | 0.0344 (12) | 0.0598 (16) | 0.0041 (14) | 0.0351 (17) | 0.0037 (11) |
C25 | 0.084 (2) | 0.0435 (14) | 0.0615 (16) | −0.0152 (14) | 0.0203 (15) | −0.0097 (12) |
C26 | 0.0585 (15) | 0.0439 (13) | 0.0584 (15) | −0.0052 (11) | 0.0108 (12) | −0.0087 (11) |
C31 | 0.0330 (10) | 0.0453 (12) | 0.0378 (10) | 0.0022 (9) | 0.0075 (8) | 0.0037 (9) |
C32 | 0.0635 (16) | 0.0516 (15) | 0.0603 (16) | −0.0116 (13) | 0.0116 (13) | 0.0003 (12) |
C33 | 0.083 (2) | 0.0578 (18) | 0.100 (3) | −0.0168 (16) | 0.019 (2) | 0.0209 (18) |
C34 | 0.0669 (19) | 0.090 (2) | 0.081 (2) | 0.0028 (17) | 0.0261 (17) | 0.041 (2) |
C35 | 0.0621 (17) | 0.105 (3) | 0.0443 (14) | 0.0128 (17) | 0.0149 (13) | 0.0211 (15) |
C36 | 0.0534 (14) | 0.0641 (16) | 0.0412 (12) | 0.0022 (12) | 0.0047 (11) | 0.0015 (11) |
N1 | 0.0436 (9) | 0.0373 (9) | 0.0383 (9) | 0.0003 (8) | 0.0061 (7) | 0.0036 (7) |
N2 | 0.0486 (10) | 0.0472 (11) | 0.0415 (10) | −0.0010 (9) | 0.0118 (8) | 0.0043 (8) |
C11 | 0.0376 (11) | 0.0377 (11) | 0.0481 (12) | −0.0057 (8) | 0.0120 (9) | −0.0107 (9) |
C12 | 0.0602 (16) | 0.0659 (16) | 0.0554 (15) | −0.0148 (13) | 0.0236 (13) | −0.0094 (13) |
C13 | 0.071 (2) | 0.087 (2) | 0.087 (2) | −0.0274 (18) | 0.047 (2) | −0.0282 (19) |
C14 | 0.0470 (15) | 0.071 (2) | 0.129 (3) | −0.0104 (15) | 0.036 (2) | −0.039 (2) |
C15 | 0.0417 (14) | 0.0596 (18) | 0.116 (3) | 0.0051 (13) | 0.0075 (16) | −0.0152 (18) |
C16 | 0.0423 (12) | 0.0517 (14) | 0.0653 (16) | 0.0035 (11) | 0.0071 (11) | −0.0039 (12) |
Ag1 | 0.05306 (12) | 0.05106 (12) | 0.03463 (10) | −0.01141 (8) | 0.00173 (8) | 0.00047 (7) |
P1 | 0.0351 (3) | 0.0382 (3) | 0.0317 (3) | −0.0029 (2) | 0.0043 (2) | −0.0018 (2) |
S1 | 0.0448 (3) | 0.0354 (3) | 0.0576 (3) | 0.0031 (2) | 0.0160 (3) | 0.0063 (2) |
C1—N2 | 1.339 (3) | C31—P1 | 1.815 (2) |
C1—N1 | 1.346 (3) | C32—C33 | 1.380 (4) |
C1—S1i | 1.746 (2) | C32—H32 | 0.9300 |
C2—N2 | 1.347 (3) | C33—C34 | 1.379 (5) |
C2—C3 | 1.372 (4) | C33—H33 | 0.9300 |
C2—C5 | 1.505 (3) | C34—C35 | 1.370 (5) |
C3—C4 | 1.373 (3) | C34—H34 | 0.9300 |
C3—H3 | 0.89 (3) | C35—C36 | 1.377 (4) |
C4—N1 | 1.343 (3) | C35—H35 | 0.9300 |
C4—C6 | 1.495 (4) | C36—H36 | 0.9300 |
C5—H5A | 0.9600 | N1—Ag1 | 2.3763 (18) |
C5—H5B | 0.9600 | C11—C12 | 1.386 (3) |
C5—H5C | 0.9600 | C11—C16 | 1.387 (4) |
C6—H6A | 0.9600 | C11—P1 | 1.818 (2) |
C6—H6B | 0.9600 | C12—C13 | 1.401 (4) |
C6—H6C | 0.9600 | C12—H12 | 0.9300 |
C21—C26 | 1.385 (3) | C13—C14 | 1.360 (6) |
C21—C22 | 1.387 (3) | C13—H13 | 0.9300 |
C21—P1 | 1.818 (2) | C14—C15 | 1.346 (5) |
C22—C23 | 1.391 (4) | C14—H14 | 0.9300 |
C22—H22 | 0.9300 | C15—C16 | 1.393 (4) |
C23—C24 | 1.367 (5) | C15—H15 | 0.9300 |
C23—H23 | 0.9300 | C16—H16 | 0.9300 |
C24—C25 | 1.362 (5) | Ag1—P1 | 2.4088 (6) |
C24—H24 | 0.9300 | Ag1—S1 | 2.5492 (6) |
C25—C26 | 1.390 (4) | Ag1—S1i | 2.7897 (6) |
C25—H25 | 0.9300 | Ag1—Ag1i | 2.9569 (4) |
C26—H26 | 0.9300 | S1—C1i | 1.746 (2) |
C31—C32 | 1.387 (4) | S1—Ag1i | 2.7897 (6) |
C31—C36 | 1.390 (3) | ||
N2—C1—N1 | 125.0 (2) | C35—C34—C33 | 120.3 (3) |
N2—C1—S1i | 118.66 (17) | C35—C34—H34 | 119.9 |
N1—C1—S1i | 116.31 (15) | C33—C34—H34 | 119.9 |
N2—C2—C3 | 121.8 (2) | C34—C35—C36 | 119.7 (3) |
N2—C2—C5 | 116.1 (3) | C34—C35—H35 | 120.2 |
C3—C2—C5 | 122.1 (3) | C36—C35—H35 | 120.2 |
C2—C3—C4 | 118.8 (2) | C35—C36—C31 | 120.9 (3) |
C2—C3—H3 | 117.6 (19) | C35—C36—H36 | 119.6 |
C4—C3—H3 | 123 (2) | C31—C36—H36 | 119.6 |
N1—C4—C3 | 120.1 (2) | C4—N1—C1 | 117.93 (19) |
N1—C4—C6 | 116.9 (2) | C4—N1—Ag1 | 137.84 (16) |
C3—C4—C6 | 122.9 (2) | C1—N1—Ag1 | 103.78 (13) |
C2—C5—H5A | 109.5 | C1—N2—C2 | 116.3 (2) |
C2—C5—H5B | 109.5 | C12—C11—C16 | 119.3 (2) |
H5A—C5—H5B | 109.5 | C12—C11—P1 | 117.4 (2) |
C2—C5—H5C | 109.5 | C16—C11—P1 | 123.23 (18) |
H5A—C5—H5C | 109.5 | C11—C12—C13 | 119.0 (3) |
H5B—C5—H5C | 109.5 | C11—C12—H12 | 120.5 |
C4—C6—H6A | 109.5 | C13—C12—H12 | 120.5 |
C4—C6—H6B | 109.5 | C14—C13—C12 | 120.9 (3) |
H6A—C6—H6B | 109.5 | C14—C13—H13 | 119.5 |
C4—C6—H6C | 109.5 | C12—C13—H13 | 119.5 |
H6A—C6—H6C | 109.5 | C15—C14—C13 | 120.1 (3) |
H6B—C6—H6C | 109.5 | C15—C14—H14 | 120.0 |
C26—C21—C22 | 118.8 (2) | C13—C14—H14 | 120.0 |
C26—C21—P1 | 123.42 (18) | C14—C15—C16 | 121.0 (3) |
C22—C21—P1 | 117.80 (19) | C14—C15—H15 | 119.5 |
C21—C22—C23 | 119.9 (3) | C16—C15—H15 | 119.5 |
C21—C22—H22 | 120.1 | C11—C16—C15 | 119.7 (3) |
C23—C22—H22 | 120.1 | C11—C16—H16 | 120.2 |
C24—C23—C22 | 120.7 (3) | C15—C16—H16 | 120.2 |
C24—C23—H23 | 119.7 | N1—Ag1—P1 | 115.73 (5) |
C22—C23—H23 | 119.7 | N1—Ag1—S1 | 114.96 (5) |
C25—C24—C23 | 119.8 (3) | P1—Ag1—S1 | 116.81 (2) |
C25—C24—H24 | 120.1 | N1—Ag1—S1i | 60.73 (5) |
C23—C24—H24 | 120.1 | P1—Ag1—S1i | 123.56 (2) |
C24—C25—C26 | 120.4 (3) | S1—Ag1—S1i | 112.912 (15) |
C24—C25—H25 | 119.8 | N1—Ag1—Ag1i | 84.41 (5) |
C26—C25—H25 | 119.8 | P1—Ag1—Ag1i | 155.550 (17) |
C21—C26—C25 | 120.4 (3) | S1—Ag1—Ag1i | 60.342 (16) |
C21—C26—H26 | 119.8 | S1i—Ag1—Ag1i | 52.570 (14) |
C25—C26—H26 | 119.8 | C31—P1—C11 | 105.11 (10) |
C32—C31—C36 | 118.8 (2) | C31—P1—C21 | 104.39 (10) |
C32—C31—P1 | 117.53 (18) | C11—P1—C21 | 103.96 (10) |
C36—C31—P1 | 123.68 (19) | C31—P1—Ag1 | 115.14 (7) |
C33—C32—C31 | 120.0 (3) | C11—P1—Ag1 | 115.39 (8) |
C33—C32—H32 | 120.0 | C21—P1—Ag1 | 111.66 (7) |
C31—C32—H32 | 120.0 | C1i—S1—Ag1 | 102.21 (7) |
C34—C33—C32 | 120.3 (3) | C1i—S1—Ag1i | 79.07 (7) |
C34—C33—H33 | 119.9 | Ag1—S1—Ag1i | 67.088 (15) |
C32—C33—H33 | 119.9 |
Symmetry code: (i) −x+1, −y, −z. |
D—H···A | D—H | H···A | D···A | D—H···A |
C14—H14···S1ii | 0.93 | 2.94 | 3.801 (3) | 154 |
C14—H14···N2iii | 0.93 | 2.69 | 3.471 (4) | 143 |
C35—H35···N2iv | 0.93 | 2.93 | 3.756 (4) | 151 |
Symmetry codes: (ii) x+1, y, z; (iii) −x+2, −y, −z; (iv) x, y, z+1. |
Experimental details
Crystal data | |
Chemical formula | [Ag2(C6H7N2S)2(C18H15P)2] |
Mr | 1018.67 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 293 |
a, b, c (Å) | 11.7050 (5), 15.3084 (7), 12.5331 (6) |
β (°) | 97.483 (1) |
V (Å3) | 2226.62 (18) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 1.08 |
Crystal size (mm) | 0.29 × 0.18 × 0.09 |
Data collection | |
Diffractometer | Bruker SMART CCD diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 2003) |
Tmin, Tmax | 0.793, 0.909 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 26686, 5568, 4798 |
Rint | 0.023 |
(sin θ/λ)max (Å−1) | 0.668 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.032, 0.088, 1.04 |
No. of reflections | 5568 |
No. of parameters | 266 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.54, −0.29 |
Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 2003), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), Mercury (Macrae et al., 2008), SHELXTL (Sheldrick, 2008) and publCIF (Westrip, 2010).
D—H···A | D—H | H···A | D···A | D—H···A |
C14—H14···S1i | 0.93 | 2.94 | 3.801 (3) | 154.2 |
C14—H14···N2ii | 0.93 | 2.69 | 3.471 (4) | 142.5 |
C35—H35···N2iii | 0.93 | 2.93 | 3.756 (4) | 150.5 |
Symmetry codes: (i) x+1, y, z; (ii) −x+2, −y, −z; (iii) x, y, z+1. |
Acknowledgements
We are grateful to the Department of Chemistry, and the Graduate School, Prince of Songkla University, for financial support of this work.
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In recent years, a large number of structural reports on metal(I) complexes containing heterocyclic thiones as ligands or mixed-ligands with triphenylphosphane have been studied (Aslanidis et al., 1997; McFarlane et al., 1998; Pakawatchai et al., 2012; Nimthong et al., 2012) because of not only their potential applications due to their antimicrobial activities (Nawaz et al., 2011), but also strongly luminescent properties (Hameau et al., 2012).
The structure of the title dinuclear mixed-ligand complex displays the distorted tetrahedral coordination of each AgI center, which exhibits a planar Ag2S2 moiety in which each of the doubly S-bridged AgI centers is surrounded by the one P atom of phosphane ligand and one N atom of the dmpymtH ligands (Fig. 1). The Ag—Ag distance of 2.9569 (4) Å in the four-membered Ag2S2 ring is shorter than in [Ag2X2(l-S-pySH)2(PPh3)2] (X = Cl and Br), 3.8425 (8) and 3.8211 (4) Å, respectively (Lobana et al., 2008) and also shorter than the sum of the covalent radii of two AgI centers (3.44 Å). Focusing on the comparison of bond distances and bond angles around the AgI ion, the Ag—S bond lengths [2.5492 (6)–2.7897 (6) Å] are in good agreement with values reported for other silver(I) complexes with heterocyclic thione ligands, such as 2.5548 (9) Å for [Ag(PPh3)(pymtH)Br]2 (Cox et al., 2000) and 2.537 (2) Å for [Ag(Ph3P)(Diaz)2]2(NO3)2 (Nawaz et al., 2011). The Ag1—P1 bond length of 2.4088 (6) Å is similar to that found in [Ag(PPh3)(thiourea)(NO3)]2.[Ag(PPh3)(thiourea)]2(NO3)2 [2.4029 (10)–2.4157 (10) Å] (Isab et al., 2010). The two S1–Ag1–P1 angles of 116.81 (2) and 123.56 (2)° are larger than the normal tetrahedral value of 109.5°. In the crystal, the intermolecular interactions C14(sp2)—H14···N2 [H14···N2 = 2.686 (4) Å, C14(sp2)···N2 = 3.471 (4) Å and C14(sp2)—H14···N2 = 142.52 (8)°] and C14(sp2)—H14···S1 [H14···S1 = 2.942 (3) Å, C14(sp2)···S1 = 3.801 (3) Å and C14(sp2)—H14···S1 = 154.18 (9)°] form chains (Fig. 2). Moreover, secondary interactions C35(sp2)—H35···N2 [H35···N2 = 2.928 (4) Å, C35(sp2)···N2 = 3.756 (4) Å and C35(sp2)—H35···N2 = 150.48 (7)°] are also observed, which form the two-dimensional layer network (Fig. 3).