Poly[[bis­[μ2-1,3-bis­(phenyl­sulfan­yl)propane-κ2S:S′]silver(I)] hexa­fluorido­anti­monate diethyl ether hemisolvate]

Awaleh, M.O.; Badia, A.; Brisse, F.

doi:10.1107/S1600536807056371

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Poly[[bis[μ₂-1,3-bis(phenylsulfanyl)propane-κ²S:S′]silver(I)] hexafluoridoantimonate diethyl ether hemisolvate]

M. O. Awaleh, A. Badia and F. Brisse

The title compound, {[Ag(C₁₅H₁₆S₂)₂]SbF₆·0.5C₄H₁₀O}_n, was obtained from the self-assembly of AgSbF₆ and 1,3-bis(phenylsulfanyl)propane. Each Ag^I ion is coordinated by four S atoms from different ligands, forming a distorted tethrahedral geometry. Each ligand links adjacent Ag^I ions, forming an extended two-dimensional grid-like framework. SbF₆⁻ ions, which are incorporated into the cavities of the network, complete and stabilize the structure. One of the phenyl rings is disordered over two sites, the ratio of occupancies being 0.508 (4):0.492 (4).

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807056371/lh2544sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807056371/lh2544Isup2.hkl Contains datablock I

CCDC reference: 656135

checkCIF report

Key indicators

Single-crystal X-ray study
T = 220 K
Mean (C-C) = 0.008 Å
Disorder in main residue
R factor = 0.044
wR factor = 0.114
Data-to-parameter ratio = 18.9

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT601_ALERT_2_B Structure Contains Solvent Accessible VOIDS of .     199.00 A   3 

Alert level C
CHEMW03_ALERT_2_C The ratio of given/expected molecular weight as
            calculated from the _atom_site* data lies outside
            the range 0.99 <> 1.01
           From the CIF: _cell_formula_units_Z                    4
           From the CIF: _chemical_formula_weight           901.52
           TEST: Calculate formula weight from _atom_site_*
           atom     mass    num     sum
           C        12.01   30.00  360.33
           H         1.01   32.00   32.26
           F        19.00    6.00  113.99
           S        32.07    4.00  128.26
           Ag      107.87    1.00  107.87
           Sb      121.75    1.00  121.75
           Calculated formula weight              864.46
PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings    Differ ....          ?
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT043_ALERT_1_C Check Reported Molecular Weight ................     901.52
PLAT044_ALERT_1_C Calculated and Reported Dx Differ ..............          ?
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for        Sb1
PLAT301_ALERT_3_C Main Residue  Disorder .........................      15.00 Perc.

Alert level G
FORMU01_ALERT_2_G  There is a discrepancy between the atom counts in the
            _chemical_formula_sum and the formula from the _atom_site* data.
            Atom count from _chemical_formula_sum:C32 H37 Ag1 F6 O0.5 S4 Sb1
            Atom count from the _atom_site data:  C30 H32 Ag1 F6 S4 Sb1
CELLZ01_ALERT_1_G Difference between formula and atom_site contents detected.
CELLZ01_ALERT_1_G ALERT: Large difference may be due to a
            symmetry error - see SYMMG tests
           From the CIF: _cell_formula_units_Z    4
           From the CIF: _chemical_formula_sum  C32 H37 Ag F6 O0.5 S4 Sb
           TEST: Compare cell contents of formula and atom_site data

           atom    Z*formula  cif sites diff
           C        128.00    120.00    8.00
           H        148.00    128.00   20.00
           Ag         4.00      4.00    0.00
           F         24.00     24.00    0.00
           O          2.00      0.00    2.00
           S         16.00     16.00    0.00
           Sb         4.00      4.00    0.00

   0 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
   7 ALERT level C = Check and explain
   3 ALERT level G = General alerts; check

   6 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   3 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Comment top

The self-assembly of metal-organic coordination polymers has attracted a great attention because of their potential as functional materials (Millward & Yaghi, 2005; Wong-Foy et al., 2006). When flexible ligands are involved in supramolecular architectures, the prediction of the topology of the coordination polymer is more difficult because there are several factors affecting the framework formation, such as the type of solvent, the counter-anion, and the metal-to-ligand ratio among others (Withersby et al., 1999, 1997; Noro et al., 2002; Black et al., 1995; Blake et al., 1999; Bu et al., 2002; Carlucci et al., 2002). Neverthless, in order to gain more information about those subtle factors, not yet well understood, we have studied the effect of one parameter at a time on the topology of the networks (Awaleh et al., 2006a,b; 2007). In our continuous effort to study the structure of the metal-organic supramolecular architecture, we report herein a silver(I) coordination polymer forming a lamellar network by using a flexible dithioether, viz. 1,3-bis(phenylsulfanyl)propane (L^3-Ph), as building block, namely Poly[Silver(I)-di-µ-1,3-bis(phenylsulfanyl)propane]hexafluoroantimonate acetone solvate (I). In the title complex (I), each Ag^I center is linked in a tetrahedral manner to a sulfur atom of four different L^3-Ph ligands (Fig. 1). The other sulfur atom of each ligand is bound to a neighbouring Ag^I ion thus forming a two-dimensional cationic coordination polymer where the repeat unit is a rectangular 24-membered macrometallocycle Ag₄(L^3-Ph)₄ (Fig. 2). The phenyl groups of the L^3-Ph ligands are located on the same side of the Ag₄ plane. The dihedral angle between the phenyl groups is 71.6(20°. The PF₆^- ions are incorporated in the cavities of the repeating unit to balance the charge of the cationic coordination polymer (Fig. 3). Neighbouring rectangular rings are fused in a parquet-like pattern to form an infinite lamellar (4,4) coordination network (Fig. 3).

Related literature top

For related literature, see: Awaleh et al. (2006a, 2006b, 2007); Black et al. (1995); Blake et al. (1999); Bu et al. (2002); Carlucci et al. (2002); Hartley et al. (1979); Hou et al. (2005); Millward & Yaghi (2005); Noro et al. (2002); Sluis & Spek (1990); Spek (2003); Withersby et al. (1997, 1999); Wong-Foy, Matzger & Yaghi (2006).

Experimental top

The ligand 1,3-bis(phenylsulfanyl)propane, L^3-Ph, was synthesized following a publish report (Hartley et al., 1979). For the synthesis of the title compound (I), a solution of AgSbF₆ (164 mg, 0.48 mmol) in acetone (5 ml) was added a solution of L^3-Ph (0.22 ml, 0.95 mmol) in diethyl ether (5 ml). The mixture was kept under reflux at 323 K for 2 h. The filtrate was recrystallized by diffusion of petroleum ether into the solution at room temperature. A few days later, single crystals suitable for X-ray analysis were deposited. Yield 74% based on AgSbF₆. Anal. Found: C, 42.46; H, 3.84. Calculated for C₃₂H₃₇S₄O_0.5AgSbF₆: C, 42.63; H, 4.14. ¹H NMR (DMSO-d₆, 400 MHz): d 1.84 (qt, 2H, –S-(CH₂)-(CH₂)-), 3.07 (t, 4H, –S-(CH₂)-), 7.28–7.59 (m, 10H, C₆H₅–). ¹⁹F NMR (DMSO-d₆, 376.31 MHz): d -137.49 - -102.91 (m, F—Sb).

Computing details top

Data collection: SMART (Bruker, 1999); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT (Bruker, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: UdMX (local program; Maris, 2004).

Figures top

	Fig. 1. The aysmmetric unit of the title compound. Ellipsoid are drawn at the 30% probability level. The disordered components are labeled with suffixes A and B.
	Fig. 2. View of the 24-membered Ag₄(L^3-Ph)₄ macrometallocyclic repeat unit of the title compound.
	Fig. 3. View of the two-dimensional molecular-rectangle network of the title compound.

Poly[[bis[µ₂-1,3-bis(phenylsulfanyl)propane-κ²S:S']silver(I)] hexafluoridoantimonate diethyl ether hemisolvate] top

Crystal data top

[Ag(C₁₅H₁₆S₂)₂]SbF₆·0.5C₄H₁₀O	F(000) = 1712
M_r = 901.52	D_x = 1.657 Mg m⁻³
Monoclinic, P2₁/c	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: -P 2ybc	Cell parameters from 7995 reflections
a = 13.5794 (2) Å	θ = 3.3–72.8°
b = 13.0497 (2) Å	µ = 12.87 mm⁻¹
c = 20.5848 (3) Å	T = 220 K
β = 97.791 (1)°	Block, colorless
V = 3614.10 (9) Å³	0.27 × 0.14 × 0.11 mm
Z = 4

Data collection top

Bruker SMART 2K diffractometer	7095 independent reflections
Radiation source: X-ray Sealed Tube	5413 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.049
Detector resolution: 5.5 pixels mm^-1	θ_max = 72.9°, θ_min = 3.3°
ω scans	h = −16→16
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −13→15
T_min = 0.162, T_max = 0.239	l = −25→25
43960 measured reflections

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) = 0.114	H-atom parameters constrained
S = 0.95	w = 1/[σ²(F_o²) + (0.0718P)²] where P = (F_o² + 2F_c²)/3
7095 reflections	(Δ/σ)_max = 0.001
375 parameters	Δρ_max = 1.07 e Å⁻³
0 restraints	Δρ_min = −0.92 e Å⁻³

Crystal data top

[Ag(C₁₅H₁₆S₂)₂]SbF₆·0.5C₄H₁₀O	V = 3614.10 (9) Å³
M_r = 901.52	Z = 4
Monoclinic, P2₁/c	Cu Kα radiation
a = 13.5794 (2) Å	µ = 12.87 mm⁻¹
b = 13.0497 (2) Å	T = 220 K
c = 20.5848 (3) Å	0.27 × 0.14 × 0.11 mm
β = 97.791 (1)°

Data collection top

Bruker SMART 2K diffractometer	7095 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	5413 reflections with I > 2σ(I)
T_min = 0.162, T_max = 0.239	R_int = 0.049
43960 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	0 restraints
wR(F²) = 0.114	H-atom parameters constrained
S = 0.95	Δρ_max = 1.07 e Å⁻³
7095 reflections	Δρ_min = −0.92 e Å⁻³
375 parameters

Special details top

Experimental. X-ray crystallographic data for I were collected from a single-crystal sample, which was mounted on a loop fiber. Data were collected using a Bruker Platform diffractometer, equipped with a Bruker SMART 2 K Charged-Coupled Device (CCD) Area Detector using the program SMART and normal focus sealed tube source graphite monochromated Cu—Kα radiation. The crystal-to-detector distance was 4.908 cm, and the data collection was carried out in 512 x 512 pixel mode, utilizing 4 x 4 pixel binning. The initial unit-cell parameters were determined by a least-squares fit of the angular setting of strong reflections, collected by a 9.0 degree scan in 30 frames over four different parts of the reciprocal space (120 frames total). One complete sphere of data was collected, to better than 0.8Å resolution. Upon completion of the data collection, the first 101 frames were recollected in order to improve the decay correction analysis.

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.

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
Ag1	0.25367 (2)	0.61376 (3)	0.245888 (17)	0.02260 (10)
Sb1	0.22596 (3)	0.08152 (3)	0.166843 (17)	0.03613 (11)
S1	0.21540 (8)	0.77327 (9)	0.31534 (6)	0.0215 (2)
S2	0.34586 (8)	0.48708 (9)	0.32496 (6)	0.0252 (3)
S3	0.08207 (8)	0.56386 (9)	0.18682 (6)	0.0227 (2)
S4	0.35897 (8)	0.69189 (9)	0.16407 (6)	0.0247 (3)
F1	0.1398 (3)	0.1928 (3)	0.1844 (2)	0.0678 (12)
F2	0.3345 (3)	0.1719 (4)	0.1855 (2)	0.0820 (15)
F3	0.3054 (3)	−0.0257 (4)	0.1523 (2)	0.0916 (17)
F4	0.1130 (3)	−0.0011 (3)	0.15182 (17)	0.0519 (9)
F5	0.2087 (3)	0.1186 (4)	0.07860 (18)	0.0787 (15)
F6	0.2400 (3)	0.0490 (3)	0.25589 (16)	0.0488 (9)
C11	0.1783 (3)	0.7220 (4)	0.3894 (2)	0.0218 (10)
C12	0.0832 (4)	0.6887 (4)	0.3940 (2)	0.0291 (11)
H12	0.0343	0.6927	0.3578	0.035*
C13	0.0607 (4)	0.6496 (4)	0.4522 (3)	0.0368 (13)
H13	−0.0039	0.6285	0.4555	0.044*
C14	0.1326 (5)	0.6415 (4)	0.5055 (3)	0.0444 (15)
H14	0.1172	0.6140	0.5445	0.053*
C15	0.2281 (5)	0.6742 (4)	0.5010 (3)	0.0394 (14)
H15	0.2769	0.6687	0.5372	0.047*
C16	0.2515 (4)	0.7153 (4)	0.4431 (3)	0.0330 (12)
H16	0.3157	0.7382	0.4402	0.040*
C17	0.1015 (4)	0.8260 (4)	0.2720 (2)	0.0251 (10)
H17A	0.1135	0.8492	0.2290	0.030*
H17B	0.0513	0.7726	0.2659	0.030*
C18	0.0624 (3)	0.9153 (4)	0.3087 (2)	0.0231 (10)
H18A	0.1110	0.9701	0.3135	0.028*
H18B	0.0518	0.8931	0.3523	0.028*
C21	0.2527 (3)	0.4021 (4)	0.3470 (2)	0.0244 (10)
C22	0.2337 (4)	0.3056 (4)	0.3204 (3)	0.0284 (11)
H22	0.2714	0.2799	0.2896	0.034*
C23	0.1570 (4)	0.2476 (4)	0.3405 (3)	0.0317 (12)
H23	0.1438	0.1824	0.3233	0.038*
C24	0.1006 (4)	0.2860 (4)	0.3857 (3)	0.0339 (12)
H24	0.0488	0.2472	0.3983	0.041*
C25	0.1208 (4)	0.3818 (5)	0.4123 (3)	0.0394 (14)
H25	0.0829	0.4073	0.4431	0.047*
C26	0.1969 (4)	0.4401 (4)	0.3935 (3)	0.0318 (12)
H26	0.2108	0.5044	0.4119	0.038*
C27	0.4222 (4)	0.4080 (4)	0.2802 (3)	0.0278 (11)
H27A	0.3797	0.3680	0.2480	0.033*
H27B	0.4632	0.4517	0.2567	0.033*
C28	0.4891 (4)	0.3357 (4)	0.3247 (2)	0.0270 (11)
H28A	0.5309	0.3752	0.3575	0.032*
H28B	0.4485	0.2901	0.3471	0.032*
C31	0.1094 (3)	0.5131 (4)	0.1110 (2)	0.0211 (10)
C32	0.1117 (4)	0.5836 (4)	0.0602 (2)	0.0277 (11)
H32	0.0979	0.6523	0.0668	0.033*
C33	0.1343 (4)	0.5510 (4)	0.0005 (3)	0.0329 (12)
H33	0.1368	0.5982	−0.0331	0.040*
C34	0.1534 (4)	0.4484 (4)	−0.0101 (3)	0.0377 (14)
H34	0.1681	0.4267	−0.0507	0.045*
C35	0.1503 (4)	0.3783 (4)	0.0401 (3)	0.0373 (13)
H35	0.1629	0.3094	0.0330	0.045*
C36	0.1286 (4)	0.4100 (4)	0.1007 (3)	0.0290 (11)
H36	0.1268	0.3627	0.1344	0.035*
C37	0.0354 (3)	0.4546 (4)	0.2285 (2)	0.0243 (10)
H37A	0.0844	0.4001	0.2321	0.029*
H37B	0.0251	0.4746	0.2724	0.029*
C41A	0.4293 (6)	0.5788 (5)	0.1447 (4)	0.025 (2)	0.508 (4)
C42A	0.3748 (4)	0.4987 (6)	0.1131 (4)	0.0391 (19)	0.508 (4)
H42A	0.3068	0.5057	0.1007	0.047*	0.508 (4)
C43A	0.4222 (5)	0.4079 (5)	0.1002 (4)	0.052 (3)	0.508 (4)
H43A	0.3857	0.3543	0.0791	0.062*	0.508 (4)
C44A	0.5239 (5)	0.3973 (5)	0.1188 (4)	0.044 (2)	0.508 (4)
H44A	0.5556	0.3366	0.1102	0.053*	0.508 (4)
C45A	0.5784 (4)	0.4775 (7)	0.1504 (4)	0.035 (3)	0.508 (4)
H45A	0.6465	0.4704	0.1628	0.042*	0.508 (4)
C46A	0.5311 (6)	0.5682 (6)	0.1633 (4)	0.0285 (12)	0.508 (4)
H46A	0.5675	0.6218	0.1844	0.034*	0.508 (4)
C41B	0.4365 (7)	0.6062 (6)	0.1305 (4)	0.025 (2)	0.492 (4)
C42B	0.3977 (5)	0.5663 (6)	0.0698 (4)	0.0391 (19)	0.492 (4)
H42B	0.3347	0.5859	0.0502	0.047*	0.492 (4)
C43B	0.4529 (6)	0.4970 (7)	0.0383 (3)	0.052 (3)	0.492 (4)
H43B	0.4270	0.4703	−0.0023	0.062*	0.492 (4)
C44B	0.5470 (5)	0.4676 (6)	0.0676 (4)	0.044 (2)	0.492 (4)
H44B	0.5840	0.4213	0.0465	0.053*	0.492 (4)
C45B	0.5858 (5)	0.5075 (7)	0.1283 (4)	0.035 (3)	0.492 (4)
H45B	0.6487	0.4879	0.1479	0.042*	0.492 (4)
C46B	0.5305 (7)	0.5768 (7)	0.1598 (3)	0.0285 (12)	0.492 (4)
H46B	0.5565	0.6036	0.2004	0.034*	0.492 (4)
C47	0.4461 (3)	0.7731 (4)	0.2149 (2)	0.0264 (11)
H47A	0.4094	0.8192	0.2398	0.032*
H47B	0.4882	0.7307	0.2458	0.032*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ag1	0.01757 (16)	0.02028 (19)	0.0306 (2)	−0.00137 (12)	0.00575 (13)	−0.00095 (13)
Sb1	0.0370 (2)	0.0407 (2)	0.0296 (2)	−0.00904 (16)	0.00059 (15)	0.00587 (15)
S1	0.0170 (5)	0.0194 (6)	0.0280 (6)	0.0012 (4)	0.0021 (4)	−0.0011 (4)
S2	0.0197 (6)	0.0202 (6)	0.0369 (7)	0.0017 (4)	0.0081 (5)	0.0011 (5)
S3	0.0186 (5)	0.0191 (6)	0.0307 (6)	−0.0026 (4)	0.0046 (5)	−0.0005 (4)
S4	0.0158 (5)	0.0276 (7)	0.0305 (6)	−0.0043 (4)	0.0028 (5)	0.0039 (5)
F1	0.079 (3)	0.044 (2)	0.072 (3)	0.024 (2)	−0.020 (2)	−0.0084 (19)
F2	0.069 (3)	0.106 (4)	0.067 (3)	−0.053 (3)	−0.006 (2)	0.015 (3)
F3	0.081 (3)	0.109 (4)	0.084 (3)	0.059 (3)	0.005 (3)	−0.019 (3)
F4	0.044 (2)	0.057 (2)	0.052 (2)	−0.0191 (18)	−0.0046 (17)	0.0042 (17)
F5	0.078 (3)	0.118 (4)	0.037 (2)	−0.032 (3)	−0.003 (2)	0.025 (2)
F6	0.056 (2)	0.050 (2)	0.038 (2)	−0.0002 (17)	−0.0038 (17)	0.0128 (15)
C11	0.024 (2)	0.018 (3)	0.023 (2)	0.0038 (18)	0.0019 (19)	−0.0032 (18)
C12	0.032 (3)	0.026 (3)	0.029 (3)	0.003 (2)	0.006 (2)	0.003 (2)
C13	0.039 (3)	0.038 (3)	0.037 (3)	0.007 (2)	0.017 (3)	0.003 (2)
C14	0.072 (5)	0.032 (3)	0.032 (3)	0.010 (3)	0.016 (3)	−0.001 (2)
C15	0.059 (4)	0.032 (3)	0.023 (3)	0.007 (3)	−0.009 (3)	−0.004 (2)
C16	0.039 (3)	0.024 (3)	0.033 (3)	0.001 (2)	−0.006 (2)	−0.004 (2)
C17	0.026 (3)	0.024 (3)	0.025 (3)	0.0081 (19)	0.003 (2)	−0.0015 (19)
C18	0.017 (2)	0.022 (3)	0.029 (3)	0.0027 (18)	0.0012 (19)	−0.0025 (19)
C21	0.021 (2)	0.021 (3)	0.031 (3)	0.0000 (18)	0.004 (2)	0.0051 (19)
C22	0.023 (2)	0.027 (3)	0.036 (3)	0.003 (2)	0.004 (2)	−0.001 (2)
C23	0.029 (3)	0.020 (3)	0.043 (3)	−0.004 (2)	−0.003 (2)	0.003 (2)
C24	0.031 (3)	0.025 (3)	0.046 (3)	−0.008 (2)	0.006 (2)	0.007 (2)
C25	0.042 (3)	0.044 (4)	0.036 (3)	−0.005 (3)	0.019 (3)	0.000 (3)
C26	0.039 (3)	0.020 (3)	0.039 (3)	−0.001 (2)	0.013 (2)	−0.001 (2)
C27	0.025 (3)	0.028 (3)	0.032 (3)	0.002 (2)	0.012 (2)	0.002 (2)
C28	0.021 (2)	0.028 (3)	0.032 (3)	0.0011 (19)	0.006 (2)	0.000 (2)
C31	0.014 (2)	0.020 (3)	0.028 (3)	−0.0007 (17)	0.0016 (18)	0.0035 (18)
C32	0.023 (2)	0.028 (3)	0.031 (3)	−0.0026 (19)	−0.001 (2)	0.008 (2)
C33	0.034 (3)	0.035 (3)	0.029 (3)	−0.012 (2)	0.000 (2)	0.009 (2)
C34	0.039 (3)	0.042 (4)	0.033 (3)	−0.019 (3)	0.009 (3)	−0.006 (2)
C35	0.045 (3)	0.025 (3)	0.042 (3)	0.002 (2)	0.009 (3)	−0.003 (2)
C36	0.031 (3)	0.020 (3)	0.037 (3)	0.0004 (19)	0.008 (2)	0.004 (2)
C37	0.022 (2)	0.028 (3)	0.022 (3)	−0.0086 (19)	0.0019 (19)	0.0016 (19)
C41A	0.018 (3)	0.031 (6)	0.027 (5)	−0.007 (3)	0.009 (3)	0.000 (4)
C42A	0.025 (4)	0.043 (5)	0.048 (5)	0.008 (3)	−0.003 (4)	−0.009 (3)
C43A	0.041 (5)	0.060 (7)	0.051 (6)	0.010 (4)	−0.010 (4)	−0.031 (4)
C44A	0.036 (5)	0.045 (6)	0.053 (6)	0.008 (4)	0.012 (4)	−0.012 (4)
C45A	0.023 (3)	0.050 (7)	0.033 (6)	−0.001 (4)	0.008 (4)	−0.005 (5)
C46A	0.022 (3)	0.030 (3)	0.032 (3)	−0.001 (2)	0.000 (2)	0.002 (2)
C41B	0.018 (3)	0.031 (6)	0.027 (5)	−0.007 (3)	0.009 (3)	0.000 (4)
C42B	0.025 (4)	0.043 (5)	0.048 (5)	0.008 (3)	−0.003 (4)	−0.009 (3)
C43B	0.041 (5)	0.060 (7)	0.051 (6)	0.010 (4)	−0.010 (4)	−0.031 (4)
C44B	0.036 (5)	0.045 (6)	0.053 (6)	0.008 (4)	0.012 (4)	−0.012 (4)
C45B	0.023 (3)	0.050 (7)	0.033 (6)	−0.001 (4)	0.008 (4)	−0.005 (5)
C46B	0.022 (3)	0.030 (3)	0.032 (3)	−0.001 (2)	0.000 (2)	0.002 (2)
C47	0.019 (2)	0.026 (3)	0.033 (3)	−0.0031 (19)	0.002 (2)	−0.004 (2)

Geometric parameters (Å, º) top

Ag1—S2	2.5293 (12)	C26—H26	0.93
Ag1—S3	2.5621 (12)	C27—C28	1.526 (7)
Ag1—S4	2.5639 (12)	C27—H27a	0.97
Ag1—S1	2.6170 (12)	C27—H27b	0.97
Sb1—F3	1.816 (4)	C28—C47ⁱⁱ	1.517 (6)
Sb1—F5	1.864 (4)	C28—H28a	0.97
Sb1—F6	1.866 (3)	C28—H28b	0.97
Sb1—F4	1.866 (3)	C31—C36	1.392 (7)
Sb1—F2	1.886 (4)	C31—C32	1.395 (6)
Sb1—F1	1.929 (4)	C32—C33	1.374 (7)
S1—C11	1.799 (5)	C32—H32	0.93
S1—C17	1.814 (5)	C33—C34	1.387 (8)
S2—C21	1.786 (5)	C33—H33	0.93
S2—C27	1.802 (5)	C34—C35	1.385 (8)
S3—C31	1.781 (5)	C34—H34	0.93
S3—C37	1.820 (5)	C35—C36	1.384 (7)
S4—C41b	1.741 (6)	C35—H35	0.93
S4—C47	1.811 (5)	C36—H36	0.93
S4—C41a	1.831 (6)	C37—C18ⁱⁱⁱ	1.530 (6)
C11—C12	1.378 (7)	C37—H37a	0.97
C11—C16	1.385 (7)	C37—H37b	0.97
C12—C13	1.374 (7)	C41a—C42a	1.39
C12—H12	0.93	C41a—C46a	1.39
C13—C14	1.371 (8)	C42a—C43a	1.39
C13—H13	0.93	C42a—H42a	0.93
C14—C15	1.379 (9)	C43a—C44a	1.39
C14—H14	0.93	C43a—H43a	0.93
C15—C16	1.384 (7)	C44a—C45a	1.39
C15—H15	0.93	C44a—H44a	0.93
C16—H16	0.93	C45a—C46a	1.39
C17—C18	1.523 (6)	C45a—H45a	0.93
C17—H17a	0.97	C46a—H46a	0.93
C17—H17b	0.97	C41b—C42b	1.39
C18—C37ⁱ	1.530 (6)	C41b—C46b	1.39
C18—H18a	0.97	C42b—C43b	1.39
C18—H18b	0.97	C42b—H42b	0.93
C21—C22	1.384 (7)	C43b—C44b	1.39
C21—C26	1.390 (7)	C43b—H43b	0.93
C22—C23	1.396 (7)	C44b—C45b	1.39
C22—H22	0.93	C44b—H44b	0.93
C23—C24	1.377 (7)	C45b—C46b	1.39
C23—H23	0.93	C45b—H45b	0.93
C24—C25	1.378 (8)	C46b—H46b	0.93
C24—H24	0.93	C47—C28^iv	1.517 (6)
C25—C26	1.380 (7)	C47—H47a	0.97
C25—H25	0.93	C47—H47b	0.97

S2—Ag1—S3	118.58 (4)	C25—C26—H26	120.2
S2—Ag1—S4	114.28 (4)	C21—C26—H26	120.2
S3—Ag1—S4	109.98 (4)	C28—C27—S2	112.5 (4)
S2—Ag1—S1	106.61 (4)	C28—C27—H27A	109.1
S3—Ag1—S1	103.08 (4)	S2—C27—H27A	109.1
S4—Ag1—S1	102.26 (4)	C28—C27—H27B	109.1
F3—SB1—F5	92.2 (2)	S2—C27—H27B	109.1
F3—SB1—F6	90.18 (19)	H27A—C27—H27B	107.8
F5—SB1—F6	177.6 (2)	C47ⁱⁱ—C28—C27	110.6 (4)
F3—SB1—F4	91.2 (2)	C47ⁱⁱ—C28—H28A	109.5
F5—SB1—F4	89.82 (17)	C27—C28—H28A	109.5
F6—SB1—F4	90.21 (15)	C47ⁱⁱ—C28—H28B	109.5
F3—SB1—F2	92.9 (2)	C27—C28—H28B	109.5
F5—SB1—F2	91.56 (18)	H28A—C28—H28B	108.1
F6—SB1—F2	88.24 (17)	C36—C31—C32	120.0 (5)
F4—SB1—F2	175.6 (2)	C36—C31—S3	123.9 (4)
F3—SB1—F1	178.1 (2)	C32—C31—S3	116.1 (4)
F5—SB1—F1	89.3 (2)	C33—C32—C31	119.8 (5)
F6—SB1—F1	88.32 (16)	C33—C32—H32	120.1
F4—SB1—F1	87.73 (18)	C31—C32—H32	120.1
F2—SB1—F1	88.2 (2)	C32—C33—C34	120.6 (5)
C11—S1—C17	103.9 (2)	C32—C33—H33	119.7
C11—S1—AG1	105.44 (15)	C34—C33—H33	119.7
C17—S1—AG1	104.63 (16)	C35—C34—C33	119.7 (5)
C21—S2—C27	104.6 (2)	C35—C34—H34	120.2
C21—S2—AG1	105.26 (16)	C33—C34—H34	120.2
C27—S2—AG1	108.28 (17)	C34—C35—C36	120.5 (5)
C31—S3—C37	104.4 (2)	C34—C35—H35	119.7
C31—S3—AG1	103.08 (15)	C36—C35—H35	119.7
C37—S3—AG1	109.11 (16)	C35—C36—C31	119.5 (5)
C41B—S4—C47	102.9 (3)	C35—C36—H36	120.3
C47—S4—C41A	106.2 (3)	C31—C36—H36	120.3
C41B—S4—AG1	115.2 (3)	C18ⁱⁱⁱ—C37—S3	111.2 (3)
C47—S4—AG1	103.42 (16)	C18ⁱⁱⁱ—C37—H37A	109.4
C41A—S4—AG1	100.2 (3)	S3—C37—H37A	109.4
C12—C11—C16	120.3 (5)	C18ⁱⁱⁱ—C37—H37B	109.4
C12—C11—S1	123.2 (4)	S3—C37—H37B	109.4
C16—C11—S1	116.5 (4)	H37A—C37—H37B	108
C13—C12—C11	119.9 (5)	C42A—C41A—C46A	120
C13—C12—H12	120.1	C42A—C41A—S4	116.6 (5)
C11—C12—H12	120.1	C46A—C41A—S4	123.3 (5)
C14—C13—C12	120.5 (6)	C41A—C42A—C43A	120
C14—C13—H13	119.8	C41A—C42A—H42A	120
C12—C13—H13	119.8	C43A—C42A—H42A	120
C13—C14—C15	119.8 (6)	C42A—C43A—C44A	120
C13—C14—H14	120.1	C42A—C43A—H43A	120
C15—C14—H14	120.1	C44A—C43A—H43A	120
C14—C15—C16	120.3 (5)	C45A—C44A—C43A	120
C14—C15—H15	119.8	C45A—C44A—H44A	120
C16—C15—H15	119.8	C43A—C44A—H44A	120
C15—C16—C11	119.2 (5)	C46A—C45A—C44A	120
C15—C16—H16	120.4	C46A—C45A—H45A	120
C11—C16—H16	120.4	C44A—C45A—H45A	120
C18—C17—S1	112.2 (3)	C45A—C46A—C41A	120
C18—C17—H17A	109.2	C45A—C46A—H46A	120
S1—C17—H17A	109.2	C41A—C46A—H46A	120
C18—C17—H17B	109.2	C42B—C41B—C46B	120
S1—C17—H17B	109.2	C42B—C41B—S4	114.9 (5)
H17A—C17—H17B	107.9	C46B—C41B—S4	125.1 (5)
C17—C18—C37ⁱ	110.2 (4)	C43B—C42B—C41B	120
C17—C18—H18A	109.6	C43B—C42B—H42B	120
C37ⁱ—C18—H18A	109.6	C41B—C42B—H42B	120
C17—C18—H18B	109.6	C42B—C43B—C44B	120
C37ⁱ—C18—H18B	109.6	C42B—C43B—H43B	120
H18A—C18—H18B	108.1	C44B—C43B—H43B	120
C22—C21—C26	120.5 (5)	C43B—C44B—C45B	120
C22—C21—S2	124.4 (4)	C43B—C44B—H44B	120
C26—C21—S2	115.1 (4)	C45B—C44B—H44B	120
C21—C22—C23	118.9 (5)	C46B—C45B—C44B	120
C21—C22—H22	120.6	C46B—C45B—H45B	120
C23—C22—H22	120.6	C44B—C45B—H45B	120
C24—C23—C22	120.6 (5)	C45B—C46B—C41B	120
C24—C23—H23	119.7	C45B—C46B—H46B	120
C22—C23—H23	119.7	C41B—C46B—H46B	120
C25—C24—C23	120.0 (5)	C28^iv—C47—S4	112.7 (3)
C25—C24—H24	120	C28^iv—C47—H47A	109
C23—C24—H24	120	S4—C47—H47A	109
C24—C25—C26	120.4 (5)	C28^iv—C47—H47B	109
C24—C25—H25	119.8	S4—C47—H47B	109
C26—C25—H25	119.8	H47A—C47—H47B	107.8
C25—C26—C21	119.7 (5)

S2—AG1—S1—C11	−41.29 (16)	C24—C25—C26—C21	0.7 (9)
S3—AG1—S1—C11	84.28 (16)	C22—C21—C26—C25	−1.3 (8)
S4—AG1—S1—C11	−161.55 (16)	S2—C21—C26—C25	177.8 (4)
S2—AG1—S1—C17	−150.52 (17)	C21—S2—C27—C28	−73.9 (4)
S3—AG1—S1—C17	−24.95 (18)	AG1—S2—C27—C28	174.3 (3)
S4—AG1—S1—C17	89.22 (17)	S2—C27—C28—C47ⁱⁱ	−178.4 (3)
S3—AG1—S2—C21	−20.62 (18)	C37—S3—C31—C36	−22.9 (5)
S4—AG1—S2—C21	−152.88 (17)	AG1—S3—C31—C36	91.1 (4)
S1—AG1—S2—C21	94.94 (18)	C37—S3—C31—C32	157.5 (4)
S3—AG1—S2—C27	90.76 (18)	AG1—S3—C31—C32	−88.5 (4)
S4—AG1—S2—C27	−41.50 (19)	C36—C31—C32—C33	−1.0 (7)
S1—AG1—S2—C27	−153.68 (18)	S3—C31—C32—C33	178.6 (4)
S2—AG1—S3—C31	−94.61 (16)	C31—C32—C33—C34	1.0 (8)
S4—AG1—S3—C31	39.51 (16)	C32—C33—C34—C35	−0.5 (8)
S1—AG1—S3—C31	147.95 (16)	C33—C34—C35—C36	−0.2 (9)
S2—AG1—S3—C37	15.91 (18)	C34—C35—C36—C31	0.2 (8)
S4—AG1—S3—C37	150.04 (18)	C32—C31—C36—C35	0.4 (7)
S1—AG1—S3—C37	−101.52 (18)	S3—C31—C36—C35	−179.2 (4)
S2—AG1—S4—C41B	42.0 (3)	C31—S3—C37—C18ⁱⁱⁱ	−64.9 (4)
S3—AG1—S4—C41B	−94.2 (3)	AG1—S3—C37—C18ⁱⁱⁱ	−174.5 (3)
S1—AG1—S4—C41B	156.8 (3)	C41B—S4—C41A—C42A	−109 (2)
S2—AG1—S4—C47	−69.39 (17)	C47—S4—C41A—C42A	171.7 (4)
S3—AG1—S4—C47	154.36 (17)	AG1—S4—C41A—C42A	64.4 (4)
S1—AG1—S4—C47	45.38 (17)	C41B—S4—C41A—C46A	75 (2)
S2—AG1—S4—C41A	40.1 (3)	C47—S4—C41A—C46A	−4.4 (5)
S3—AG1—S4—C41A	−96.2 (3)	AG1—S4—C41A—C46A	−111.7 (4)
S1—AG1—S4—C41A	154.9 (3)	C46A—C41A—C42A—C43A	0
C17—S1—C11—C12	27.0 (5)	S4—C41A—C42A—C43A	−176.3 (6)
AG1—S1—C11—C12	−82.7 (4)	C41A—C42A—C43A—C44A	0
C17—S1—C11—C16	−154.1 (4)	C42A—C43A—C44A—C45A	0
AG1—S1—C11—C16	96.2 (4)	C43A—C44A—C45A—C46A	0
C16—C11—C12—C13	0.6 (8)	C44A—C45A—C46A—C41A	0
S1—C11—C12—C13	179.5 (4)	C42A—C41A—C46A—C45A	0
C11—C12—C13—C14	−1.3 (8)	S4—C41A—C46A—C45A	176.0 (6)
C12—C13—C14—C15	1.0 (9)	C47—S4—C41B—C42B	−152.3 (4)
C13—C14—C15—C16	0.0 (9)	C41A—S4—C41B—C42B	103 (2)
C14—C15—C16—C11	−0.8 (8)	AG1—S4—C41B—C42B	95.9 (5)
C12—C11—C16—C15	0.4 (7)	C47—S4—C41B—C46B	27.7 (6)
S1—C11—C16—C15	−178.5 (4)	C41A—S4—C41B—C46B	−77 (2)
C11—S1—C17—C18	64.8 (4)	AG1—S4—C41B—C46B	−84.0 (5)
AG1—S1—C17—C18	175.1 (3)	C46B—C41B—C42B—C43B	0
S1—C17—C18—C37ⁱ	−178.1 (3)	S4—C41B—C42B—C43B	−179.9 (6)
C27—S2—C21—C22	−13.7 (5)	C41B—C42B—C43B—C44B	0
AG1—S2—C21—C22	100.3 (4)	C42B—C43B—C44B—C45B	0
C27—S2—C21—C26	167.2 (4)	C43B—C44B—C45B—C46B	0
AG1—S2—C21—C26	−78.8 (4)	C44B—C45B—C46B—C41B	0
C26—C21—C22—C23	0.7 (7)	C42B—C41B—C46B—C45B	0
S2—C21—C22—C23	−178.4 (4)	S4—C41B—C46B—C45B	179.9 (7)
C21—C22—C23—C24	0.5 (8)	C41B—S4—C47—C28^iv	65.1 (5)
C22—C23—C24—C25	−1.1 (8)	C41A—S4—C47—C28^iv	80.4 (5)
C23—C24—C25—C26	0.5 (9)	AG1—S4—C47—C28^iv	−174.7 (3)

Symmetry codes: (i) −x, y+1/2, −z+1/2; (ii) −x+1, y−1/2, −z+1/2; (iii) −x, y−1/2, −z+1/2; (iv) −x+1, y+1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	[Ag(C₁₅H₁₆S₂)₂]SbF₆·0.5C₄H₁₀O
M_r	901.52
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	220
a, b, c (Å)	13.5794 (2), 13.0497 (2), 20.5848 (3)
β (°)	97.791 (1)
V (Å³)	3614.10 (9)
Z	4
Radiation type	Cu Kα
µ (mm⁻¹)	12.87
Crystal size (mm)	0.27 × 0.14 × 0.11

Data collection
Diffractometer	Bruker SMART 2K diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.162, 0.239
No. of measured, independent and observed [I > 2σ(I)] reflections	43960, 7095, 5413
R_int	0.049
(sin θ/λ)_max (Å⁻¹)	0.620

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.114, 0.95
No. of reflections	7095
No. of parameters	375
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.07, −0.92

Computer programs: SMART (Bruker, 1999), SAINT (Bruker, 1999), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1997), UdMX (local program; Maris, 2004).

Selected geometric parameters (Å, º) top

Ag1—S2	2.5293 (12)	Ag1—S4	2.5639 (12)
Ag1—S3	2.5621 (12)	Ag1—S1	2.6170 (12)

S2—Ag1—S3	118.58 (4)	S2—Ag1—S1	106.61 (4)
S2—Ag1—S4	114.28 (4)	S3—Ag1—S1	103.08 (4)
S3—Ag1—S4	109.98 (4)	S4—Ag1—S1	102.26 (4)

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