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Acta Cryst. (2007). E63, m2063-m2064    [ doi:10.1107/S1600536807031431 ]

Hexakis([mu]3-N,N-diisopropyldithiocarbamato)hexasilver(I)(6 Ag-Ag)

X. Yin, M.-B. Xie, W.-G. Zhang, J. Fan and M. Zeller

Abstract top

The title AgI complex, [Ag6(C7H14NS2)6], was obtained by the reaction of Ag(NO3) with Na(iPrDTC) in a 1:1 molar ratio in methanol (iPrDTC = N,N-diisopropyldithiocarbamate). The centrosymmetric hexanuclear structure comprises two Ag3S3 units which are held together by the S atoms of the thiocarbamate groups. The Ag...Ag distances range from 3.0382 (5) to 3.0985 (5) Å. One of the diisopropylamino groups is disordered over two positions, with site occupancy factors of ca 0.6 and 0.4.

Comment top

Since their first description by Akerström (1959) AgI complexes with dialkyldithiocarbamates have been widely studied owing to their variable coordination modes and, for complexes containing the Ag—Ag metal bonds, also due to their potential photoluminescent properties. Differently substituted alkyl groups and reaction conditions may play crucial roles in the formation of a variety of complexes with unprecedented structures (Ebihara et al., 1994; Liu et al., 2006; Song et al., 2006).

Early crystallographic studies revealed the hexameric nature of Ag_S2CNR2 (R = Et, Pr and n-Bu) complexes in the solid state (Anacker-Eickhoff et al., 1963; Zhang et al., 2002). Recently we synthesized the title iPrDTC complex, (I), (iPrDTC = N,N-diisopropyldithiocarbamate).

In the solid state the title complex (I) has a hexameric structure similar to those described earlier with a core formed by two cyclohexane-like Ag3S3 rings stacked atop of each other (Fig.1). There are two types of S atoms: S2, S4 and S5 and their symmetry equivalents are coordinated to only one Ag atom each with Ag—S distances of 2.4798 (15), 2.5034 (13) and 2.4879 (15) Å. The remaining three crystallographically independent S atoms (S1, S3 and S6), on the other hand, are acting as bridges between each two Ag atoms with Ag—S distances between 2.4626 (13) and 2.6123 (12) Å. Each three Ag and three of these S atoms are forming the cyclohexane-like rings, which are bridged to each other via six Ag—Ag bonds (3.0382 (5)–3.0985 (5) Å). These distances are longer than those in metallic Ag (2.886 Å, Greenwood & Earnshaw, 1989), but still shorter than the sum of the Van der Waals radii of two Ag atoms (3.44 Å, Tang et al., 1997). This thus may suggest to classify these interactions as weakly argentophilic. The thiocarbamato groups are, on the other hand, acting as clamps holding the two six-membered rings together with the mono-coordinated sulfur atoms S2, S4 and S5 (and their symmetry equivalents) bridging over to the other half of the molecule. This seems to be the more likely cause for the close contacts between the two six-membered rings, and the close Ag—Ag contacts may just be a side effect of the stronger forces exerted by the chelating ligands. The thiocarbamato groups themselves exhibit the expected planar geometry with basically sp2 hybridized N atoms.

Related literature top

For related literature, see: Akerström (1959); Anacker-Eickhoff et al., (1982); Ebihara et al., (1994); Fan et al., (2004); Liu et al., (2006); Song et al., (2006); Tang et al., (2004); Zhang et al., (2002); Greenwood & Earnshaw (1989).

Experimental top

Synthesis of sodium N,N-diisopropyldithiocarbamate, Na(iPrDTC) was carried out according to the literature procedure (Fan et al., 2004), with N,N'-diisopropylamine substituted for N,N'-dibenzylamine. Silver nitrate (0.17 g, 1.0 mmol) was added slowly to Na(iPrDTC) (0.20 g, 1.0 mmol) in methanol solution (15 ml) with stirring. Then, a pale yellow solution was formed after 24 h. Some pale yellow crystals of the title complex (I) suitable for structure determination were obtained in 40% yield by slow evaporation for the filtrate of silver complex after some weeks.

Refinement top

One of the diisopropylamine groups has both isopropylamines disordered over two positions with a site occupancy ratio of 0.57 (2):0.43 (2). The C—C distances within each isopropyl group were restrained to be the same within a standard deviation of 0.02 Å, rigid bond restraints were applied (DELU commands, standard deviation 0.01), and the atoms within the isopropyl groups were restrained to have the same Uij components (SIMU commands, standard deviation 0.01). The central N-bonded C (C17 and C20) were restrained to be isotropic within a standard deviation of 0.01, and equivalent disordered C atoms were set to have identical anisotropic displacement parameters.

All H atoms were placed in calculated positions with C—H = 0.96(methyl) and 0.98 Å (C—H) and refined with Uiso(H) = 1.2Ueq (C). Methyl H atoms were allowed to rotate to best fit the experimental electron density.

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1998); software used to prepare material for publication: SHELXTL.

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound (I), with 50% probability displacement ellipsoids (H atoms are omitted for clarity).
Hexa-µ3-N,N-diisopropyldithiocarbamato-hexasilver(I)(6 A g—Ag) top
Crystal data top
[Ag6(C7H14NS2)6]Z = 1
Mr = 1705.21F(000) = 852
Triclinic, P1Dx = 1.757 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 11.5958 (2) ÅCell parameters from 1000 reflections
b = 12.4826 (3) Åθ = 2.0–25.0°
c = 12.7543 (2) ŵ = 2.21 mm−1
α = 84.083 (1)°T = 293 K
β = 78.825 (1)°Block, pale-yellow
γ = 62.874 (1)°0.20 × 0.20 × 0.15 mm
V = 1611.69 (6) Å3
Data collection top
Bruker SMART APEXII
diffractometer		5779 independent reflections
Radiation source: fine-focus sealed tube4071 reflections with I > 2σ(I)
graphiteRint = 0.033
φ and ω scansθmax = 25.2°, θmin = 1.8°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −12→13
Tmin = 0.666, Tmax = 0.733k = −14→13
16354 measured reflectionsl = −15→15
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.037Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.088H-atom parameters constrained
S = 1.05 w = 1/[σ2(Fo2) + (0.0371P)2 + 0.1926P]
where P = (Fo2 + 2Fc2)/3
5779 reflections(Δ/σ)max = 0.001
333 parametersΔρmax = 0.56 e Å−3
60 restraintsΔρmin = −0.52 e Å−3
Crystal data top
[Ag6(C7H14NS2)6]γ = 62.874 (1)°
Mr = 1705.21V = 1611.69 (6) Å3
Triclinic, P1Z = 1
a = 11.5958 (2) ÅMo Kα radiation
b = 12.4826 (3) ŵ = 2.21 mm−1
c = 12.7543 (2) ÅT = 293 K
α = 84.083 (1)°0.20 × 0.20 × 0.15 mm
β = 78.825 (1)°
Data collection top
Bruker SMART APEXII
diffractometer		5779 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		4071 reflections with I > 2σ(I)
Tmin = 0.666, Tmax = 0.733Rint = 0.033
16354 measured reflectionsθmax = 25.2°
Refinement top
R[F2 > 2σ(F2)] = 0.037H-atom parameters constrained
wR(F2) = 0.088Δρmax = 0.56 e Å−3
S = 1.05Δρmin = −0.52 e Å−3
5779 reflectionsAbsolute structure: ?
333 parametersFlack parameter: ?
60 restraintsRogers parameter: ?
Special details top

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
xyzUiso*/UeqOcc. (<1)
C20.3470 (7)0.6466 (6)0.0839 (4)0.111 (2)
H2A0.36870.56250.09090.167*
H2B0.38830.66220.01530.167*
H2C0.25350.69310.09040.167*
C30.3950 (5)0.6810 (5)0.1704 (4)0.0669 (14)
H30.49050.64670.14830.080*
C40.3496 (6)0.8151 (5)0.1763 (5)0.098 (2)
H4A0.39000.83000.22850.147*
H4B0.25580.85520.19660.147*
H4C0.37440.84510.10770.147*
C50.5925 (5)0.5950 (6)0.3133 (4)0.0918 (19)
H5A0.54430.67130.34820.138*
H5B0.62720.60690.24080.138*
H5C0.66340.54310.35040.138*
C60.5018 (5)0.5380 (5)0.3142 (4)0.0693 (15)
H60.47870.51620.38860.083*
C70.5673 (6)0.4230 (6)0.2504 (7)0.132 (3)
H7A0.50840.38710.25750.198*
H7B0.64610.36770.27690.198*
H7C0.58890.44130.17640.198*
C90.2875 (6)0.2859 (6)−0.0444 (5)0.106 (2)
H9A0.21940.3458−0.08010.159*
H9B0.35380.2292−0.09550.159*
H9C0.32590.3240−0.01050.159*
C100.2308 (5)0.2222 (5)0.0375 (4)0.0740 (15)
H100.19720.1839−0.00390.089*
C110.3296 (7)0.1179 (5)0.0940 (6)0.117 (2)
H11A0.28400.09220.15440.176*
H11B0.38700.14290.11780.176*
H11C0.38030.05230.04550.176*
C12−0.0466 (7)0.3541 (7)−0.0128 (6)0.131 (3)
H12A−0.04160.4292−0.02460.197*
H12B−0.13430.3673−0.01530.197*
H12C0.01370.2987−0.06740.197*
C13−0.0119 (6)0.3030 (6)0.0942 (4)0.0889 (19)
H13−0.08190.35830.14690.107*
C14−0.0086 (9)0.1823 (9)0.1203 (7)0.168 (4)
H14A−0.00520.16440.19500.252*
H14B0.06770.12210.07880.252*
H14C−0.08630.18290.10380.252*
C16A0.364 (2)−0.171 (3)0.503 (2)0.099 (5)0.567 (17)
H16A0.4493−0.18530.51500.149*0.567 (17)
H16B0.3496−0.13370.43430.149*0.567 (17)
H16C0.3599−0.24650.50610.149*0.567 (17)
C17A0.2593 (12)−0.0890 (10)0.5893 (13)0.081 (3)0.567 (17)
H17A0.2843−0.12940.65720.098*0.567 (17)
C18A0.1173 (14)−0.0634 (19)0.5966 (18)0.097 (4)0.567 (17)
H18A0.0680−0.02560.66330.146*0.567 (17)
H18B0.1124−0.13750.59250.146*0.567 (17)
H18C0.0814−0.01070.53860.146*0.567 (17)
C16B0.327 (3)−0.149 (4)0.489 (3)0.099 (5)0.433 (17)
H16D0.3614−0.11060.43080.149*0.433 (17)
H16E0.2903−0.19310.46120.149*0.433 (17)
H16F0.3960−0.20260.52670.149*0.433 (17)
C17B0.2370 (15)−0.0685 (14)0.5524 (16)0.081 (3)0.433 (17)
H17B0.1787−0.02000.50150.098*0.433 (17)
C18B0.142 (2)−0.101 (3)0.631 (2)0.097 (4)0.433 (17)
H18D0.0569−0.03230.64090.146*0.433 (17)
H18E0.1726−0.12430.69830.146*0.433 (17)
H18F0.1351−0.16640.60390.146*0.433 (17)
C19A0.240 (4)0.020 (4)0.787 (2)0.121 (8)0.567 (17)
H19A0.15060.07790.78380.181*0.567 (17)
H19B0.26800.03830.84620.181*0.567 (17)
H19C0.2447−0.05910.79760.181*0.567 (17)
C20A0.3259 (14)0.025 (3)0.6862 (11)0.084 (4)0.567 (17)
H20A0.32740.10290.68570.101*0.567 (17)
C21A0.4650 (14)−0.068 (2)0.682 (2)0.115 (6)0.567 (17)
H21A0.5153−0.06280.61430.172*0.567 (17)
H21B0.4683−0.14630.69180.172*0.567 (17)
H21C0.5010−0.05370.73820.172*0.567 (17)
C19B0.243 (6)0.067 (5)0.785 (3)0.121 (8)0.433 (17)
H19D0.17650.04100.80800.181*0.433 (17)
H19E0.20320.15260.77140.181*0.433 (17)
H19F0.29650.04890.83950.181*0.433 (17)
C20B0.3260 (19)0.005 (5)0.6870 (14)0.084 (4)0.433 (17)
H20B0.3428−0.07810.70490.101*0.433 (17)
C21B0.4590 (19)−0.007 (3)0.651 (3)0.115 (6)0.433 (17)
H21D0.4922−0.04150.58150.172*0.433 (17)
H21E0.5150−0.05780.70040.172*0.433 (17)
H21F0.45720.07120.64800.172*0.433 (17)
N10.3763 (3)0.6231 (3)0.2760 (3)0.0501 (9)
N20.1125 (4)0.3024 (3)0.1115 (3)0.0544 (10)
N30.2622 (4)0.0295 (3)0.5920 (3)0.0601 (10)
C10.2593 (4)0.6399 (4)0.3313 (3)0.0496 (11)
C80.1157 (4)0.3679 (4)0.1861 (3)0.0473 (11)
C150.2239 (4)0.1282 (4)0.5297 (3)0.0490 (11)
S10.25423 (12)0.55930 (11)0.45194 (9)0.0539 (3)
S20.11601 (13)0.74066 (13)0.29098 (12)0.0763 (4)
S3−0.03418 (12)0.45673 (11)0.26684 (9)0.0567 (3)
S40.25532 (13)0.37190 (14)0.20131 (10)0.0700 (4)
S50.16170 (14)0.13468 (14)0.41742 (11)0.0767 (4)
S60.24215 (11)0.25148 (11)0.56300 (10)0.0548 (3)
Ag10.21579 (4)0.38209 (4)0.40089 (3)0.06482 (14)
Ag2−0.00718 (4)0.61920 (4)0.33669 (3)0.06672 (14)
Ag3−0.03051 (4)0.33627 (4)0.44546 (3)0.06702 (14)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C20.114 (5)0.169 (7)0.064 (4)−0.075 (5)−0.017 (3)0.003 (4)
C30.062 (3)0.086 (4)0.051 (3)−0.036 (3)−0.004 (2)0.013 (3)
C40.091 (5)0.081 (5)0.121 (5)−0.047 (4)−0.013 (4)0.034 (4)
C50.051 (3)0.137 (6)0.088 (4)−0.043 (4)−0.016 (3)0.005 (4)
C60.039 (3)0.086 (4)0.073 (3)−0.025 (3)−0.006 (2)0.021 (3)
C70.071 (5)0.076 (5)0.219 (9)−0.004 (4)−0.027 (5)−0.010 (5)
C90.094 (5)0.130 (6)0.080 (4)−0.057 (4)0.036 (3)−0.013 (4)
C100.070 (4)0.073 (4)0.064 (3)−0.025 (3)0.015 (3)−0.021 (3)
C110.105 (6)0.071 (4)0.127 (6)−0.004 (4)0.003 (4)−0.016 (4)
C120.137 (7)0.151 (7)0.141 (6)−0.076 (6)−0.082 (5)0.012 (5)
C130.074 (4)0.137 (6)0.077 (4)−0.065 (4)0.005 (3)−0.038 (4)
C140.205 (10)0.239 (11)0.156 (8)−0.191 (10)−0.024 (7)0.029 (7)
C16A0.098 (11)0.082 (9)0.114 (8)−0.037 (8)−0.002 (8)−0.032 (7)
C17A0.090 (5)0.063 (5)0.099 (7)−0.043 (4)−0.011 (5)−0.001 (5)
C18A0.095 (7)0.085 (11)0.128 (12)−0.060 (7)−0.013 (6)0.011 (7)
C16B0.098 (11)0.082 (9)0.114 (8)−0.037 (8)−0.002 (8)−0.032 (7)
C17B0.090 (5)0.063 (5)0.099 (7)−0.043 (4)−0.011 (5)−0.001 (5)
C18B0.095 (7)0.085 (11)0.128 (12)−0.060 (7)−0.013 (6)0.011 (7)
C19A0.113 (6)0.17 (3)0.096 (5)−0.067 (18)−0.003 (4)−0.064 (13)
C20A0.076 (4)0.075 (10)0.085 (4)−0.019 (4)−0.026 (3)0.021 (3)
C21A0.068 (4)0.15 (2)0.123 (14)−0.038 (8)−0.038 (5)0.004 (12)
C19B0.113 (6)0.17 (3)0.096 (5)−0.067 (18)−0.003 (4)−0.064 (13)
C20B0.076 (4)0.075 (10)0.085 (4)−0.019 (4)−0.026 (3)0.021 (3)
C21B0.068 (4)0.15 (2)0.123 (14)−0.038 (8)−0.038 (5)0.004 (12)
N10.041 (2)0.059 (2)0.049 (2)−0.024 (2)−0.0029 (17)0.0038 (17)
N20.051 (2)0.060 (2)0.049 (2)−0.024 (2)0.0031 (17)−0.0124 (19)
N30.054 (3)0.049 (3)0.075 (3)−0.024 (2)0.002 (2)−0.008 (2)
C10.044 (3)0.050 (3)0.059 (3)−0.026 (2)−0.002 (2)−0.008 (2)
C80.050 (3)0.044 (3)0.042 (2)−0.019 (2)−0.003 (2)0.002 (2)
C150.031 (2)0.048 (3)0.062 (3)−0.014 (2)−0.001 (2)−0.006 (2)
S10.0520 (7)0.0636 (8)0.0502 (6)−0.0318 (6)−0.0016 (5)−0.0014 (6)
S20.0441 (8)0.0757 (10)0.0974 (10)−0.0191 (7)−0.0148 (7)0.0167 (8)
S30.0424 (7)0.0658 (8)0.0525 (6)−0.0173 (6)0.0001 (5)−0.0101 (6)
S40.0477 (8)0.0978 (11)0.0695 (8)−0.0370 (8)−0.0050 (6)−0.0098 (7)
S50.0630 (9)0.0913 (11)0.0757 (9)−0.0287 (8)−0.0170 (7)−0.0200 (8)
S60.0459 (7)0.0489 (7)0.0698 (7)−0.0218 (6)−0.0055 (6)−0.0071 (6)
Ag10.0569 (3)0.0674 (3)0.0746 (3)−0.0306 (2)−0.01761 (19)0.0068 (2)
Ag20.0528 (3)0.0668 (3)0.0729 (3)−0.0160 (2)−0.01406 (19)−0.0149 (2)
Ag30.0492 (2)0.0961 (3)0.0570 (2)−0.0345 (2)−0.00242 (17)−0.0089 (2)
Geometric parameters (Å, °) top
C2—C31.504 (7)C16B—H16E0.9600
C2—H2A0.9600C16B—H16F0.9600
C2—H2B0.9600C17B—C18B1.512 (15)
C2—H2C0.9600C17B—N31.532 (12)
C3—N11.487 (5)C17B—H17B0.9800
C3—C41.515 (7)C18B—H18D0.9600
C3—H30.9800C18B—H18E0.9600
C4—H4A0.9600C18B—H18F0.9600
C4—H4B0.9600C19A—C20A1.486 (19)
C4—H4C0.9600C19A—H19A0.9600
C5—C61.513 (7)C19A—H19B0.9600
C5—H5A0.9600C19A—H19C0.9600
C5—H5B0.9600C20A—C21A1.491 (19)
C5—H5C0.9600C20A—N31.511 (11)
C6—N11.498 (6)C20A—H20A0.9800
C6—C71.519 (8)C21A—H21A0.9600
C6—H60.9800C21A—H21B0.9600
C7—H7A0.9600C21A—H21C0.9600
C7—H7B0.9600C19B—C20B1.46 (2)
C7—H7C0.9600C19B—H19D0.9600
C9—C101.481 (7)C19B—H19E0.9600
C9—H9A0.9600C19B—H19F0.9600
C9—H9B0.9600C20B—C21B1.46 (2)
C9—H9C0.9600C20B—N31.475 (13)
C10—N21.489 (6)C20B—H20B0.9800
C10—C111.514 (7)C21B—H21D0.9600
C10—H100.9800C21B—H21E0.9600
C11—H11A0.9600C21B—H21F0.9600
C11—H11B0.9600N1—C11.335 (5)
C11—H11C0.9600N2—C81.333 (5)
C12—C131.494 (8)N3—C151.334 (5)
C12—H12A0.9600C1—S21.703 (5)
C12—H12B0.9600C1—S11.756 (4)
C12—H12C0.9600C8—S41.690 (5)
C13—C141.494 (9)C8—S31.759 (4)
C13—N21.497 (6)C15—S51.703 (4)
C13—H130.9800C15—S61.750 (5)
C14—H14A0.9600S1—Ag3i2.4686 (12)
C14—H14B0.9600S1—Ag12.6123 (12)
C14—H14C0.9600S2—Ag22.4798 (15)
C16A—C17A1.522 (18)S3—Ag22.4626 (13)
C16A—H16A0.9600S3—Ag32.5934 (13)
C16A—H16B0.9600S4—Ag12.5034 (13)
C16A—H16C0.9600S5—Ag32.4879 (15)
C17A—N31.499 (10)S6—Ag12.4742 (13)
C17A—C18A1.512 (14)S6—Ag2i2.5943 (12)
C17A—H17A0.9800Ag2—S6i2.5943 (12)
C18A—H18A0.9600Ag3—S1i2.4686 (12)
C18A—H18B0.9600Ag1—Ag23.0755 (5)
C18A—H18C0.9600Ag1—Ag33.0985 (5)
C16B—C17B1.28 (3)Ag2—Ag3i3.0382 (5)
C16B—H16D0.9600Ag3—Ag2i3.0382 (5)
C3—C2—H2A109.5H18D—C18B—H18E109.5
C3—C2—H2B109.5C17B—C18B—H18F109.5
H2A—C2—H2B109.5H18D—C18B—H18F109.5
C3—C2—H2C109.5H18E—C18B—H18F109.5
H2A—C2—H2C109.5C19A—C20A—C21A113 (3)
H2B—C2—H2C109.5C19A—C20A—N3110 (2)
N1—C3—C2113.9 (4)C21A—C20A—N3116.1 (17)
N1—C3—C4113.5 (4)C19A—C20A—H20A105.7
C2—C3—C4113.9 (5)C21A—C20A—H20A105.7
N1—C3—H3104.8N3—C20A—H20A105.7
C2—C3—H3104.8C20B—C19B—H19D109.5
C4—C3—H3104.8C20B—C19B—H19E109.5
C3—C4—H4A109.5H19D—C19B—H19E109.5
C3—C4—H4B109.5C20B—C19B—H19F109.5
H4A—C4—H4B109.5H19D—C19B—H19F109.5
C3—C4—H4C109.5H19E—C19B—H19F109.5
H4A—C4—H4C109.5C19B—C20B—C21B123 (3)
H4B—C4—H4C109.5C19B—C20B—N3117 (3)
C6—C5—H5A109.5C21B—C20B—N3108 (2)
C6—C5—H5B109.5C19B—C20B—H20B101.9
H5A—C5—H5B109.5C21B—C20B—H20B101.9
C6—C5—H5C109.5N3—C20B—H20B101.9
H5A—C5—H5C109.5C20B—C21B—H21D109.5
H5B—C5—H5C109.5C20B—C21B—H21E109.5
N1—C6—C5112.4 (4)H21D—C21B—H21E109.5
N1—C6—C7109.9 (5)C20B—C21B—H21F109.5
C5—C6—C7112.6 (5)H21D—C21B—H21F109.5
N1—C6—H6107.2H21E—C21B—H21F109.5
C5—C6—H6107.2C1—N1—C3124.1 (4)
C7—C6—H6107.2C1—N1—C6121.8 (4)
C6—C7—H7A109.5C3—N1—C6114.1 (4)
C6—C7—H7B109.5C8—N2—C10123.8 (4)
H7A—C7—H7B109.5C8—N2—C13122.8 (4)
C6—C7—H7C109.5C10—N2—C13113.5 (4)
H7A—C7—H7C109.5C15—N3—C20B128 (2)
H7B—C7—H7C109.5C15—N3—C17A133.4 (8)
C10—C9—H9A109.5C15—N3—C20A119.3 (16)
C10—C9—H9B109.5C17A—N3—C20A107.3 (17)
H9A—C9—H9B109.5C15—N3—C17B112.1 (9)
C10—C9—H9C109.5C20B—N3—C17B119 (2)
H9A—C9—H9C109.5N1—C1—S2122.1 (3)
H9B—C9—H9C109.5N1—C1—S1118.5 (3)
C9—C10—N2114.7 (5)S2—C1—S1119.4 (3)
C9—C10—C11115.1 (5)N2—C8—S4122.5 (3)
N2—C10—C11113.3 (4)N2—C8—S3117.3 (3)
C9—C10—H10104.0S4—C8—S3120.2 (2)
N2—C10—H10104.0N3—C15—S5121.3 (3)
C11—C10—H10104.0N3—C15—S6119.0 (3)
C10—C11—H11A109.5S5—C15—S6119.7 (3)
C10—C11—H11B109.5C1—S1—Ag3i107.33 (15)
H11A—C11—H11B109.5C1—S1—Ag1103.96 (14)
C10—C11—H11C109.5Ag3i—S1—Ag193.55 (4)
H11A—C11—H11C109.5C1—S2—Ag298.28 (16)
H11B—C11—H11C109.5C8—S3—Ag2106.79 (15)
C13—C12—H12A109.5C8—S3—Ag3104.74 (14)
C13—C12—H12B109.5Ag2—S3—Ag396.28 (4)
H12A—C12—H12B109.5C8—S4—Ag198.69 (14)
C13—C12—H12C109.5C15—S5—Ag397.99 (15)
H12A—C12—H12C109.5C15—S6—Ag1105.32 (16)
H12B—C12—H12C109.5C15—S6—Ag2i100.09 (14)
C12—C13—C14115.0 (5)Ag1—S6—Ag2i94.86 (4)
C12—C13—N2112.4 (5)S6—Ag1—S4141.39 (5)
C14—C13—N2110.7 (6)S6—Ag1—S1104.04 (4)
C12—C13—H13106.0S4—Ag1—S1108.26 (4)
C14—C13—H13106.0S6—Ag1—Ag2134.05 (3)
N2—C13—H13106.0S4—Ag1—Ag277.03 (4)
C13—C14—H14A109.5S1—Ag1—Ag272.09 (3)
C13—C14—H14B109.5S6—Ag1—Ag375.26 (3)
H14A—C14—H14B109.5S4—Ag1—Ag397.67 (3)
C13—C14—H14C109.5S1—Ag1—Ag3131.70 (3)
H14A—C14—H14C109.5Ag2—Ag1—Ag375.187 (14)
H14B—C14—H14C109.5S3—Ag2—S2141.34 (5)
N3—C17A—C18A107.4 (13)S3—Ag2—S6i101.69 (4)
N3—C17A—C16A112.7 (17)S2—Ag2—S6i110.55 (4)
C18A—C17A—C16A120.2 (18)S3—Ag2—Ag3i132.96 (3)
N3—C17A—H17A105.1S2—Ag2—Ag3i77.49 (4)
C18A—C17A—H17A105.1S6i—Ag2—Ag3i74.78 (3)
C16A—C17A—H17A105.1S3—Ag2—Ag173.90 (3)
C17B—C16B—H16D109.5S2—Ag2—Ag198.83 (3)
C17B—C16B—H16E109.5S6i—Ag2—Ag1131.06 (3)
H16D—C16B—H16E109.5Ag3i—Ag2—Ag174.569 (13)
C17B—C16B—H16F109.5S1i—Ag3—S5142.49 (5)
H16D—C16B—H16F109.5S1i—Ag3—S3105.24 (4)
H16E—C16B—H16F109.5S5—Ag3—S3107.43 (5)
C16B—C17B—C18B119 (3)S1i—Ag3—Ag2i74.60 (3)
C16B—C17B—N3120 (3)S5—Ag3—Ag2i97.04 (3)
C18B—C17B—N3113.6 (17)S3—Ag3—Ag2i130.71 (3)
C16B—C17B—H17B99.0S1i—Ag3—Ag1134.65 (3)
C18B—C17B—H17B99.0S5—Ag3—Ag174.06 (4)
N3—C17B—H17B99.0S3—Ag3—Ag171.86 (3)
C17B—C18B—H18D109.5Ag2i—Ag3—Ag174.942 (13)
C17B—C18B—H18E109.5
Symmetry codes: (i) −x, −y+1, −z+1.
Table 1
Selected geometric parameters (Å) top
Ag1—Ag23.0755 (5)Ag2—Ag3i3.0382 (5)
Ag1—Ag33.0985 (5)Ag3—Ag2i3.0382 (5)
Symmetry codes: (i) −x, −y+1, −z+1.
Acknowledgements top

This work has been supported by the Natural Science Foundation of Guangdong Province (990463) and the National Natural Science Foundation of China (29561002).

references
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