Bis(μ-4,6-dimethyl­pyrimidine-2-thiol­ato)-κ3N,S:S;κ3S:N,S-bis­[(triphenyl­phosphane-κP)silver(I)]

Wattanakanjana, Y.; Pakawatchai, C.; Kowittheeraphong, S.; Nimthong, R.

doi:10.1107/S1600536812048210

metal-organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 68| Part 12| December 2012| Pages m1572-m1573

doi:10.1107/S1600536812048210

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Bis(μ-4,6-dimethylpyrimidine-2-thiolato)-κ³N,S:S;κ³S:N,S-bis[(triphenylphosphane-κP)silver(I)]

Yupa Wattanakanjana,^a ^* Chaveng Pakawatchai,^a Sukanya Kowittheeraphong ^a and Ruthairat Nimthong ^a

^aDepartment of Chemistry, Faculty of Science, Prince of Songkla University, Hat Yai, Songkhla 90112, Thailand
^*Correspondence e-mail: yupa.t@psu.ac.th

(Received 7 November 2012; accepted 24 November 2012; online 30 November 2012)

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 Ag^I 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 Ag^I 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

[Ag₂(C₆H₇N₂S)₂(C₁₈H₁₅P)₂]
M_r = 1018.67
Monoclinic, P 2₁ /n
a = 11.7050 (5) Å
b = 15.3084 (7) Å
c = 12.5331 (6) Å
β = 97.483 (1)°
V = 2226.62 (18) Å³
Z = 2
Mo Kα radiation
μ = 1.08 mm⁻¹
T = 293 K
0.29 × 0.18 × 0.09 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2003 ) T_min = 0.793, T_max = 0.909
26686 measured reflections
5568 independent reflections
4798 reflections with I > 2σ(I)
R_int = 0.023

Refinement

R[F² > 2σ(F²)] = 0.032
wR(F²) = 0.088
S = 1.04
5568 reflections
266 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.54 e Å⁻³
Δρ_min = −0.29 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C14—H14⋯S1ⁱ	0.93	2.94	3.801 (3)	154
C14—H14⋯N2ⁱⁱ	0.93	2.69	3.471 (4)	143
C35—H35⋯N2ⁱⁱⁱ	0.93	2.93	3.756 (4)	151
Symmetry codes: (i) x+1, y, z; (ii) -x+2, -y, -z; (iii) x, y, z+1.

Data collection: SMART (Bruker, 1998 ); cell refinement: 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

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812048210/bh2464sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812048210/bh2464Isup2.hkl

checkCIF report

Comment top

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 Ag^I center, which exhibits a planar Ag₂S₂ moiety in which each of the doubly S-bridged Ag^I 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 Ag^I centers (3.44 Å). Focusing on the comparison of bond distances and bond angles around the Ag^I 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).

Related literature top

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); Nawaz et al. (2011).

Experimental top

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.

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: 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).

Figures top

	Fig. 1. The molecular structure with displacement ellipsoids drawn at the 30% probability level.
	Fig. 2. Part of the crystal structure with C—H···N and C—H···S hydrogen bonds interactions showed as dashed lines.
	Fig. 3. The packing diagram viewed down the b axis. The dashed lines represent intermolecular C—H···N and C—H···S interactions.

Bis(µ-4,6-dimethylpyrimidine-2-thiolato)-κ³N,S:S; κ³S:N,S-bis[(triphenylphosphane-κP)silver(I)] top

Crystal data top

[Ag₂(C₆H₇N₂S)₂(C₁₈H₁₅P)₂]	F(000) = 1032
M_r = 1018.67	D_x = 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

Data collection top

Bruker SMART CCD diffractometer	5568 independent reflections
Radiation source: fine-focus sealed tube	4798 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.023
ϕ and ω scans	θ_max = 28.3°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2003)	h = −15→15
T_min = 0.793, T_max = 0.909	k = −20→20
26686 measured reflections	l = −16→16

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)] = 0.032	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(F_o²) + (0.0481P)² + 0.8969P] where P = (F_o² + 2F_c²)/3
5568 reflections	(Δ/σ)_max = 0.003
266 parameters	Δρ_max = 0.54 e Å⁻³
0 restraints	Δρ_min = −0.29 e Å⁻³
0 constraints

Crystal data top

[Ag₂(C₆H₇N₂S)₂(C₁₈H₁₅P)₂]	V = 2226.62 (18) Å³
M_r = 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)°

Data collection top

Bruker SMART CCD diffractometer	5568 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2003)	4798 reflections with I > 2σ(I)
T_min = 0.793, T_max = 0.909	R_int = 0.023
26686 measured reflections

Refinement top

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	Δρ_max = 0.54 e Å⁻³
5568 reflections	Δρ_min = −0.29 e Å⁻³
266 parameters

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

	x	y	z	U_iso*/U_eq
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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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.

Hydrogen-bond geometry (Å, º) top

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···N2^iv	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]
M_r	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)
T_min, T_max	0.793, 0.909
No. of measured, independent and observed [I > 2σ(I)] reflections	26686, 5568, 4798
R_int	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
Δρ_max, Δρ_min (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).

Hydrogen-bond geometry (Å, º) top

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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