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Acta Cryst. (2008). E64, m785    [ doi:10.1107/S1600536808012853 ]

Poly[[{[mu]4-1,2-bis[(3-cyanobenzylidene)hydrazono]-1,2-diphenylethane}bis(trifluoromethanesulfonato)disilver(I)] benzene solvate]

H. L. Li

Abstract top

In the title complex, {[Ag2(CF3O3S)2(C30H20N6)]·C6H6}n, the two independent AgI ions are each coordinated by two N atoms and one O atom in a `T-shaped' geometry. In the crystal structure, 1,2-bis[(3-cyanobenzylidene)hydrazono]-1,2-diphenylethane ligands act as bridging ligands and each coordinates to four AgI ions, resulting in a one-dimensional chain structure. The crystal structure is stabilized by weak intermolecular C-H...O hydrogen bonds.

Comment top

1,2-Bis[(3-cyanobenzylidene)hydrazono]-1,2-diphenylethane is a useful multi-dentate ligand and a three-dimensional structure was recently obtained (Liu 2008) of the compound formed by the reaction of this ligand with AgSbF6. The title one-dimensional chain structure (I) was formed when the ligand was reacted with silver(I)trifluoromethanesulfonate. It appears that the counter anions of Ag(I) complexes play a key role in the type of crystal structures formed with reactions of 1,2-bis[(3-cyanobenzylidene)hydrazono]-1,2-diphenylethane as a ligand. Herein the title crystal structure is reported.

Fig. 1 and Table 1 reveal that the coordination geometry for Ag1 and Ag2 is a 'T-shape' formed by two N atoms and a O atom, in which the two N atoms come from cyano and hydrazo groups, respectively, and the O atom is from trifluoromethanesulfonate ligand. In the crystal structure each 1,2-bis[(3-cyanobenzylidene)hydrazono]-1,2-diphenylethane ligand functions as tetradentate bridging ligand and coordinates to four AgI cations, which leads to the formation of a one-dimensional chain structure as shown in Fig. 2. In this one-dimensional chain there is 24-membered ring that includes two AgI ions. In addition, there are weak C—H···O non-classic hydrogen bonds in the chain and between neighboring chains (see Fig. 3 and Table 2).

Related literature top

For a related structure, see: Liu (2008).

Experimental top

8 ml benzene solution of AgSO3CF3 (0.0128 g, 0.05 mmol) was added very slowly on the 8 ml dichloromethane solution of 1,2-bis[(3-cyanobenzylidene)hydrazono]-1,2-diphenylethane (0.0093 g, 0.02 mmol). Colorless single crystals were obtained after the solution had been allowed to stand at room temperature for one month.

Refinement top

The H atoms were placed in calculated positions with C—H = 0.93 Å, and refined as riding with Uiso(H) = 1.2Ueq(C).

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. Part of the one-dimensional chain of the title structure showing the coordination of the two independent AgI ions. Displacement ellipsoids are shown at the 30% probability level and the benzene solvent has been omitted for clarity. [Symmetry codes: (i) x-1/2, -y+1/2, z-1/2; (ii) x+1/2, -y+1/2, z+1/2.]
[Figure 2] Fig. 2. Part of the one-dimensional chain structure showing the formation of a 24 atom ring.
[Figure 3] Fig. 3. Unit cell and part of the crystal structure showing weak C—H···O hydrogen bonds as dashed lines.
Poly[[{µ4-1,2-bis[(3-cyanobenzylidene)hydrazono]-1,2- diphenylethane}bis(trifluoromethanesulfonato)disilver(I)] benzene solvate] top
Crystal data top
[Ag2(CF3O3S)2(C30H20N6)]·C6H6F000 = 2096
Mr = 1056.51Dx = 1.716 Mg m−3
Monoclinic, P21/nMo Kα radiation
λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 7186 reflections
a = 10.8308 (9) Åθ = 2.2–27.5º
b = 22.0864 (18) ŵ = 1.14 mm−1
c = 17.0949 (13) ÅT = 298 (2) K
β = 90.420 (2)ºBlock, colorless
V = 4089.2 (6) Å30.33 × 0.23 × 0.12 mm
Z = 4
Data collection top
Bruker SMART APEX CCD
diffractometer		8891 independent reflections
Radiation source: fine-focus sealed tube6637 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.026
T = 298(2) Kθmax = 27.0º
φ and ω scansθmin = 2.1º
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −13→13
Tmin = 0.705, Tmax = 0.875k = −28→23
23919 measured reflectionsl = −20→21
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.048H-atom parameters constrained
wR(F2) = 0.134  w = 1/[σ2(Fo2) + (0.0788P)2 + 0.28P]
where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max = 0.002
8891 reflectionsΔρmax = 1.16 e Å−3
541 parametersΔρmin = −0.29 e Å−3
Primary atom site location: structure-invariant direct methodsExtinction correction: none
Crystal data top
[Ag2(CF3O3S)2(C30H20N6)]·C6H6V = 4089.2 (6) Å3
Mr = 1056.51Z = 4
Monoclinic, P21/nMo Kα
a = 10.8308 (9) ŵ = 1.14 mm−1
b = 22.0864 (18) ÅT = 298 (2) K
c = 17.0949 (13) Å0.33 × 0.23 × 0.12 mm
β = 90.420 (2)º
Data collection top
Bruker SMART APEX CCD
diffractometer		8891 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		6637 reflections with I > 2σ(I)
Tmin = 0.705, Tmax = 0.875Rint = 0.026
23919 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.048541 parameters
wR(F2) = 0.134H-atom parameters constrained
S = 1.04Δρmax = 1.16 e Å−3
8891 reflectionsΔρmin = −0.29 e Å−3
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*/Ueq
Ag10.60132 (2)0.346047 (14)0.842000 (17)0.05493 (12)
Ag2−0.00966 (3)0.327873 (17)0.633415 (18)0.06544 (13)
C10.2343 (3)0.2034 (2)1.0453 (2)0.0601 (10)
C20.1395 (3)0.24169 (17)0.9271 (2)0.0477 (8)
H20.20940.26520.91890.057*
C30.1336 (3)0.20407 (18)0.9907 (2)0.0503 (9)
C40.0299 (4)0.16746 (19)1.0033 (3)0.0601 (10)
H40.02750.14131.04580.072*
C5−0.0677 (4)0.1707 (2)0.9522 (3)0.0641 (11)
H5−0.13740.14710.96030.077*
C6−0.0627 (3)0.20939 (19)0.8882 (2)0.0542 (9)
H6−0.12970.21160.85400.065*
C70.0405 (3)0.24457 (16)0.87478 (18)0.0425 (7)
C80.1699 (5)0.1599 (3)0.7178 (4)0.0954 (18)
H80.24710.17720.72650.115*
C90.0980 (6)0.1804 (3)0.6561 (4)0.0965 (17)
H90.12880.21000.62290.116*
C10−0.0162 (6)0.1579 (3)0.6435 (4)0.0970 (18)
H10−0.06500.17260.60270.116*
C11−0.0582 (6)0.1141 (4)0.6903 (4)0.112 (2)
H11−0.13700.09860.68170.135*
C120.0122 (5)0.0917 (3)0.7507 (4)0.0990 (17)
H12−0.01800.06070.78200.119*
C130.1311 (5)0.1160 (3)0.7651 (3)0.0882 (15)
H130.18030.10180.80600.106*
C140.3169 (4)0.15481 (17)0.4787 (2)0.0525 (9)
C150.4171 (3)0.16303 (16)0.5341 (2)0.0470 (8)
C160.5166 (4)0.12303 (19)0.5335 (2)0.0605 (10)
H160.52110.09270.49590.073*
C170.4111 (3)0.20912 (16)0.58766 (18)0.0410 (7)
H170.34530.23620.58650.049*
C180.6075 (4)0.1290 (2)0.5888 (3)0.0736 (13)
H180.67340.10200.58950.088*
C190.6024 (3)0.1745 (2)0.6435 (2)0.0616 (11)
H190.66510.17820.68060.074*
C200.0456 (3)0.28326 (16)0.80567 (19)0.0455 (8)
H20−0.02200.28540.77190.055*
C210.5039 (3)0.21506 (17)0.64378 (19)0.0450 (8)
C220.5014 (3)0.26226 (17)0.70353 (19)0.0459 (8)
H220.56420.26350.74090.055*
C23−0.0077 (6)0.3590 (3)0.3969 (3)0.0921 (16)
C240.2354 (3)0.38032 (15)0.71347 (18)0.0381 (7)
C250.2541 (3)0.42213 (16)0.64852 (18)0.0413 (7)
C260.1591 (3)0.44182 (19)0.5994 (2)0.0589 (10)
H260.07920.42780.60740.071*
C270.1816 (4)0.4814 (2)0.5398 (3)0.0678 (12)
H270.11700.49270.50670.081*
C280.2958 (4)0.5046 (2)0.5275 (2)0.0652 (11)
H280.30970.53180.48690.078*
C290.3915 (4)0.4868 (2)0.5771 (2)0.0635 (11)
H290.47010.50280.57040.076*
C300.3710 (3)0.44609 (18)0.6354 (2)0.0507 (9)
H300.43650.43400.66720.061*
C310.3343 (3)0.37729 (15)0.77589 (17)0.0375 (7)
C320.3266 (3)0.41966 (16)0.84254 (19)0.0425 (7)
C330.3737 (3)0.40375 (19)0.9156 (2)0.0543 (9)
H330.40820.36560.92300.065*
C340.3697 (4)0.4441 (2)0.9768 (2)0.0688 (12)
H340.40350.43341.02510.083*
C350.2693 (4)0.4756 (2)0.8338 (2)0.0682 (11)
H350.23330.48630.78620.082*
C360.2660 (6)0.5154 (2)0.8967 (3)0.0917 (16)
H360.22910.55320.89070.110*
C370.3166 (5)0.4996 (2)0.9673 (3)0.0820 (14)
H370.31470.52681.00890.098*
C380.8438 (8)0.4793 (3)0.7793 (4)0.113 (2)
F10.9530 (6)0.4644 (4)0.7917 (5)0.262 (4)
F20.7781 (7)0.4824 (2)0.8418 (3)0.209 (3)
F3−0.0577 (5)0.3522 (2)0.3282 (3)0.1588 (19)
F40.0751 (5)0.40079 (18)0.3889 (2)0.1527 (17)
F5−0.0909 (5)0.37934 (18)0.4451 (3)0.1540 (17)
F60.8393 (6)0.5347 (2)0.7509 (3)0.185 (2)
N10.1370 (2)0.34714 (13)0.72112 (16)0.0422 (6)
N20.1421 (2)0.31398 (13)0.79151 (16)0.0432 (6)
N30.3146 (3)0.2046 (2)1.0884 (2)0.0801 (12)
N40.2379 (3)0.14639 (16)0.4371 (2)0.0646 (9)
N50.4273 (2)0.34166 (13)0.76968 (15)0.0399 (6)
N60.4161 (2)0.30172 (13)0.70622 (15)0.0435 (6)
O10.7827 (4)0.37030 (17)0.7513 (2)0.0958 (12)
O20.6537 (4)0.4471 (3)0.6981 (4)0.192 (3)
O30.8540 (3)0.43076 (19)0.6441 (2)0.0966 (11)
O40.1109 (3)0.30513 (16)0.50631 (17)0.0794 (9)
O50.1467 (2)0.27367 (15)0.37305 (17)0.0741 (9)
O6−0.0434 (3)0.24803 (15)0.4356 (2)0.0845 (10)
S10.77205 (10)0.42631 (6)0.70898 (8)0.0746 (3)
S20.05837 (9)0.28870 (5)0.43195 (6)0.0573 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ag10.04308 (17)0.0677 (2)0.05368 (19)−0.00110 (12)−0.02067 (13)−0.00059 (13)
Ag20.0565 (2)0.0816 (3)0.0578 (2)−0.01519 (15)−0.02769 (15)0.00643 (15)
C10.044 (2)0.084 (3)0.052 (2)0.0114 (19)0.0044 (18)0.019 (2)
C20.0314 (16)0.060 (2)0.0514 (19)−0.0020 (15)−0.0010 (14)0.0036 (17)
C30.0407 (18)0.062 (2)0.0479 (19)0.0072 (16)−0.0016 (15)0.0075 (17)
C40.061 (2)0.062 (3)0.058 (2)0.0010 (19)0.012 (2)0.0121 (19)
C50.044 (2)0.076 (3)0.072 (3)−0.0169 (19)0.009 (2)0.004 (2)
C60.0375 (18)0.073 (3)0.052 (2)−0.0085 (17)−0.0026 (15)−0.0030 (19)
C70.0337 (15)0.053 (2)0.0404 (17)−0.0005 (14)−0.0043 (13)−0.0016 (14)
C80.066 (3)0.109 (5)0.112 (5)−0.009 (3)0.011 (3)−0.025 (4)
C90.091 (4)0.080 (4)0.118 (5)0.006 (3)0.022 (4)−0.003 (3)
C100.102 (4)0.085 (4)0.103 (4)0.005 (3)−0.030 (4)0.005 (3)
C110.083 (4)0.126 (6)0.128 (5)−0.018 (4)−0.025 (4)−0.008 (5)
C120.095 (4)0.090 (4)0.112 (4)−0.009 (3)0.012 (4)0.001 (3)
C130.093 (4)0.095 (4)0.077 (3)0.004 (3)−0.007 (3)−0.012 (3)
C140.054 (2)0.055 (2)0.048 (2)0.0003 (17)−0.0112 (18)−0.0032 (16)
C150.0454 (18)0.053 (2)0.0421 (18)0.0015 (15)−0.0101 (15)0.0029 (15)
C160.062 (2)0.063 (3)0.056 (2)0.016 (2)−0.0106 (19)−0.0164 (19)
C170.0342 (15)0.050 (2)0.0381 (16)0.0067 (14)−0.0057 (13)−0.0013 (14)
C180.061 (3)0.077 (3)0.082 (3)0.027 (2)−0.020 (2)−0.024 (2)
C190.047 (2)0.078 (3)0.060 (2)0.0223 (19)−0.0180 (18)−0.011 (2)
C200.0355 (16)0.057 (2)0.0440 (18)−0.0007 (15)−0.0102 (14)−0.0013 (16)
C210.0361 (16)0.057 (2)0.0417 (18)0.0055 (14)−0.0062 (14)−0.0022 (15)
C220.0358 (16)0.062 (2)0.0402 (17)0.0055 (15)−0.0108 (14)−0.0021 (15)
C230.115 (5)0.083 (4)0.078 (4)0.020 (3)0.000 (3)0.006 (3)
C240.0321 (15)0.0444 (19)0.0378 (16)0.0053 (13)−0.0030 (13)−0.0060 (14)
C250.0374 (16)0.049 (2)0.0373 (16)0.0038 (14)−0.0048 (13)−0.0029 (14)
C260.0455 (19)0.063 (3)0.068 (2)−0.0023 (17)−0.0177 (18)0.014 (2)
C270.061 (2)0.068 (3)0.073 (3)0.002 (2)−0.024 (2)0.026 (2)
C280.072 (3)0.069 (3)0.055 (2)0.004 (2)0.002 (2)0.015 (2)
C290.051 (2)0.089 (3)0.051 (2)−0.007 (2)0.0028 (17)0.015 (2)
C300.0399 (17)0.074 (3)0.0385 (18)0.0030 (17)−0.0010 (14)0.0049 (17)
C310.0326 (15)0.0447 (19)0.0351 (16)−0.0020 (13)−0.0044 (12)0.0012 (13)
C320.0385 (16)0.048 (2)0.0413 (17)−0.0054 (14)−0.0021 (14)−0.0046 (14)
C330.0493 (19)0.068 (3)0.046 (2)−0.0020 (18)−0.0029 (16)−0.0052 (18)
C340.077 (3)0.086 (3)0.044 (2)−0.008 (2)−0.007 (2)−0.009 (2)
C350.093 (3)0.063 (3)0.048 (2)0.018 (2)−0.004 (2)−0.0052 (19)
C360.145 (5)0.061 (3)0.069 (3)0.021 (3)0.009 (3)−0.011 (2)
C370.123 (4)0.073 (3)0.050 (2)−0.008 (3)0.010 (3)−0.018 (2)
C380.129 (6)0.105 (5)0.104 (5)−0.002 (4)0.017 (4)−0.011 (4)
F10.155 (4)0.333 (10)0.295 (8)0.017 (5)−0.108 (5)−0.147 (7)
F20.396 (8)0.116 (3)0.116 (3)−0.016 (4)0.116 (4)−0.022 (3)
F30.196 (4)0.167 (4)0.112 (3)0.078 (3)−0.057 (3)−0.001 (3)
F40.237 (5)0.088 (3)0.133 (3)−0.040 (3)0.015 (3)0.030 (2)
F50.208 (4)0.099 (3)0.156 (3)0.081 (3)0.068 (3)0.012 (2)
F60.296 (7)0.100 (3)0.159 (4)−0.057 (4)0.074 (4)−0.009 (3)
N10.0327 (13)0.0523 (17)0.0416 (15)0.0013 (12)−0.0096 (12)−0.0005 (12)
N20.0356 (14)0.0517 (17)0.0422 (15)−0.0060 (12)−0.0108 (12)0.0046 (12)
N30.059 (2)0.122 (4)0.058 (2)0.015 (2)−0.0092 (18)0.024 (2)
N40.064 (2)0.071 (2)0.059 (2)0.0026 (17)−0.0234 (18)−0.0104 (17)
N50.0328 (13)0.0513 (17)0.0354 (14)−0.0010 (11)−0.0074 (11)−0.0039 (12)
N60.0392 (14)0.0516 (17)0.0396 (15)0.0040 (12)−0.0085 (12)−0.0077 (12)
O10.127 (3)0.083 (2)0.077 (2)0.008 (2)0.032 (2)0.0112 (19)
O20.050 (2)0.210 (6)0.316 (9)0.021 (3)−0.007 (3)0.021 (6)
O30.092 (2)0.123 (3)0.076 (2)−0.005 (2)0.0248 (19)0.014 (2)
O40.081 (2)0.096 (2)0.0608 (18)−0.0149 (18)−0.0072 (15)−0.0070 (16)
O50.0473 (14)0.105 (2)0.0699 (18)0.0017 (15)−0.0006 (14)−0.0231 (17)
O60.0638 (18)0.078 (2)0.112 (3)−0.0142 (16)0.0123 (18)−0.0275 (19)
S10.0487 (6)0.0939 (9)0.0814 (8)0.0003 (5)0.0038 (5)0.0091 (7)
S20.0507 (5)0.0619 (6)0.0591 (6)−0.0009 (4)−0.0021 (4)−0.0120 (5)
Geometric parameters (Å, °) top
Ag1—N4i2.196 (3)C22—H220.9300
Ag1—N52.249 (3)C23—F41.295 (7)
Ag1—O12.568 (3)C23—F31.299 (7)
Ag2—N3ii2.169 (3)C23—F51.305 (6)
Ag2—N12.217 (3)C23—S21.810 (6)
Ag2—O42.592 (3)C24—N11.300 (4)
C1—N31.137 (5)C24—C251.459 (5)
C1—C31.430 (5)C24—C311.508 (4)
C2—C31.371 (5)C25—C301.392 (5)
C2—C71.393 (4)C25—C261.392 (4)
C2—H20.9300C26—C271.366 (6)
C3—C41.401 (5)C26—H260.9300
C4—C51.368 (6)C27—C281.356 (6)
C4—H40.9300C27—H270.9300
C5—C61.388 (6)C28—C291.391 (6)
C5—H50.9300C28—H280.9300
C6—C71.382 (5)C29—C301.363 (5)
C6—H60.9300C29—H290.9300
C7—C201.459 (5)C30—H300.9300
C8—C131.334 (8)C31—N51.283 (4)
C8—C91.381 (9)C31—C321.477 (4)
C8—H80.9300C32—C351.390 (5)
C9—C101.349 (8)C32—C331.390 (5)
C9—H90.9300C33—C341.376 (5)
C10—C111.337 (9)C33—H330.9300
C10—H100.9300C34—C371.364 (7)
C11—C121.372 (8)C34—H340.9300
C11—H110.9300C35—C361.390 (6)
C12—C131.415 (8)C35—H350.9300
C12—H120.9300C36—C371.368 (7)
C13—H130.9300C36—H360.9300
C14—N41.124 (5)C37—H370.9300
C14—C151.447 (5)C38—F11.244 (8)
C15—C171.371 (5)C38—F21.290 (7)
C15—C161.394 (5)C38—F61.317 (8)
C16—C181.366 (5)C38—S11.846 (8)
C16—H160.9300N1—N21.410 (4)
C17—C211.391 (4)N3—Ag2i2.169 (3)
C17—H170.9300N4—Ag1ii2.196 (3)
C18—C191.374 (6)N5—N61.403 (4)
C18—H180.9300O1—S11.437 (4)
C19—C211.393 (5)O2—S11.373 (4)
C19—H190.9300O3—S11.429 (3)
C20—N21.271 (4)O4—S21.435 (3)
C20—H200.9300O5—S21.433 (3)
C21—C221.460 (5)O6—S21.423 (3)
C22—N61.271 (4)
N4i—Ag1—N5165.35 (12)F5—C23—S2111.1 (4)
N4i—Ag1—O185.26 (13)N1—C24—C25123.5 (3)
N5—Ag1—O1108.59 (11)N1—C24—C31118.8 (3)
N3ii—Ag2—N1157.73 (13)C25—C24—C31117.7 (3)
N3ii—Ag2—O494.85 (11)C30—C25—C26116.9 (3)
N1—Ag2—O4103.97 (10)C30—C25—C24119.6 (3)
N3—C1—C3178.0 (5)C26—C25—C24123.4 (3)
C3—C2—C7119.8 (3)C27—C26—C25121.0 (4)
C3—C2—H2120.1C27—C26—H26119.5
C7—C2—H2120.1C25—C26—H26119.5
C2—C3—C4120.9 (3)C28—C27—C26121.7 (4)
C2—C3—C1119.0 (3)C28—C27—H27119.2
C4—C3—C1120.1 (4)C26—C27—H27119.2
C5—C4—C3119.2 (4)C27—C28—C29118.3 (4)
C5—C4—H4120.4C27—C28—H28120.8
C3—C4—H4120.4C29—C28—H28120.8
C4—C5—C6120.1 (4)C30—C29—C28120.5 (4)
C4—C5—H5120.0C30—C29—H29119.7
C6—C5—H5120.0C28—C29—H29119.7
C7—C6—C5120.9 (3)C29—C30—C25121.5 (3)
C7—C6—H6119.6C29—C30—H30119.3
C5—C6—H6119.6C25—C30—H30119.3
C6—C7—C2119.2 (3)N5—C31—C32120.1 (3)
C6—C7—C20120.0 (3)N5—C31—C24121.5 (3)
C2—C7—C20120.9 (3)C32—C31—C24118.3 (3)
C13—C8—C9121.5 (6)C35—C32—C33118.8 (3)
C13—C8—H8119.2C35—C32—C31120.5 (3)
C9—C8—H8119.2C33—C32—C31120.7 (3)
C10—C9—C8120.8 (6)C34—C33—C32120.4 (4)
C10—C9—H9119.6C34—C33—H33119.8
C8—C9—H9119.6C32—C33—H33119.8
C11—C10—C9119.1 (6)C37—C34—C33120.5 (4)
C11—C10—H10120.4C37—C34—H34119.8
C9—C10—H10120.4C33—C34—H34119.8
C10—C11—C12121.4 (6)C32—C35—C36119.6 (4)
C10—C11—H11119.3C32—C35—H35120.2
C12—C11—H11119.3C36—C35—H35120.2
C11—C12—C13119.6 (6)C37—C36—C35120.6 (5)
C11—C12—H12120.2C37—C36—H36119.7
C13—C12—H12120.2C35—C36—H36119.7
C8—C13—C12117.4 (6)C34—C37—C36120.0 (4)
C8—C13—H13121.3C34—C37—H37120.0
C12—C13—H13121.3C36—C37—H37120.0
N4—C14—C15177.3 (4)F1—C38—F2113.8 (8)
C17—C15—C16121.1 (3)F1—C38—F6110.0 (8)
C17—C15—C14119.4 (3)F2—C38—F6103.7 (6)
C16—C15—C14119.5 (3)F1—C38—S1109.7 (5)
C18—C16—C15119.1 (4)F2—C38—S1109.9 (6)
C18—C16—H16120.4F6—C38—S1109.5 (6)
C15—C16—H16120.4C24—N1—N2110.6 (3)
C15—C17—C21119.5 (3)C24—N1—Ag2128.6 (2)
C15—C17—H17120.3N2—N1—Ag2120.05 (19)
C21—C17—H17120.3C20—N2—N1114.4 (3)
C16—C18—C19120.6 (4)C1—N3—Ag2i152.6 (4)
C16—C18—H18119.7C14—N4—Ag1ii164.0 (4)
C19—C18—H18119.7C31—N5—N6112.7 (2)
C18—C19—C21120.5 (3)C31—N5—Ag1125.7 (2)
C18—C19—H19119.8N6—N5—Ag1121.30 (19)
C21—C19—H19119.8C22—N6—N5113.6 (3)
N2—C20—C7120.2 (3)S1—O1—Ag1115.1 (2)
N2—C20—H20119.9S2—O4—Ag2126.35 (17)
C7—C20—H20119.9O2—S1—O3117.2 (4)
C17—C21—C19119.1 (3)O2—S1—O1115.3 (3)
C17—C21—C22122.2 (3)O3—S1—O1113.7 (2)
C19—C21—C22118.7 (3)O2—S1—C38105.4 (4)
N6—C22—C21122.2 (3)O3—S1—C38101.6 (3)
N6—C22—H22118.9O1—S1—C38100.8 (3)
C21—C22—H22118.9O6—S2—O5113.91 (19)
F4—C23—F3105.6 (5)O6—S2—O4115.0 (2)
F4—C23—F5107.7 (6)O5—S2—O4114.75 (17)
F3—C23—F5109.0 (6)O6—S2—C23104.5 (3)
F4—C23—S2112.0 (5)O5—S2—C23103.3 (2)
F3—C23—S2111.2 (4)O4—S2—C23103.3 (3)
C7—C2—C3—C41.2 (6)C31—C32—C35—C36−178.3 (4)
C7—C2—C3—C1−177.7 (3)C32—C35—C36—C37−1.3 (8)
C2—C3—C4—C5−1.7 (6)C33—C34—C37—C360.4 (8)
C1—C3—C4—C5177.2 (4)C35—C36—C37—C34−0.6 (9)
C3—C4—C5—C60.9 (6)C25—C24—N1—N2−176.7 (3)
C4—C5—C6—C70.5 (6)C31—C24—N1—N21.3 (4)
C5—C6—C7—C2−1.1 (6)C25—C24—N1—Ag213.6 (5)
C5—C6—C7—C20177.8 (4)C31—C24—N1—Ag2−168.4 (2)
C3—C2—C7—C60.2 (5)N3ii—Ag2—N1—C24−168.9 (4)
C3—C2—C7—C20−178.6 (3)O4—Ag2—N1—C2444.2 (3)
C13—C8—C9—C102.4 (9)N3ii—Ag2—N1—N222.2 (5)
C8—C9—C10—C11−1.7 (10)O4—Ag2—N1—N2−124.6 (2)
C9—C10—C11—C12−0.1 (11)C7—C20—N2—N1177.2 (3)
C10—C11—C12—C131.3 (10)C24—N1—N2—C20175.8 (3)
C9—C8—C13—C12−1.1 (9)Ag2—N1—N2—C20−13.5 (4)
C11—C12—C13—C8−0.7 (9)C32—C31—N5—N6176.0 (3)
C17—C15—C16—C182.0 (6)C24—C31—N5—N6−8.3 (4)
C14—C15—C16—C18−176.3 (4)C32—C31—N5—Ag1−10.2 (4)
C16—C15—C17—C21−1.9 (5)C24—C31—N5—Ag1165.5 (2)
C14—C15—C17—C21176.4 (3)N4i—Ag1—N5—C3144.1 (6)
C15—C16—C18—C19−1.3 (7)O1—Ag1—N5—C31−116.2 (3)
C16—C18—C19—C210.5 (8)N4i—Ag1—N5—N6−142.5 (4)
C6—C7—C20—N2−177.4 (3)O1—Ag1—N5—N657.1 (3)
C2—C7—C20—N21.5 (5)C21—C22—N6—N5177.6 (3)
C15—C17—C21—C191.0 (5)C31—N5—N6—C22−173.6 (3)
C15—C17—C21—C22−178.5 (3)Ag1—N5—N6—C2212.3 (4)
C18—C19—C21—C17−0.3 (6)N4i—Ag1—O1—S1−115.8 (2)
C18—C19—C21—C22179.2 (4)N5—Ag1—O1—S159.3 (3)
C17—C21—C22—N6−2.2 (6)N3ii—Ag2—O4—S210.7 (3)
C19—C21—C22—N6178.3 (4)N1—Ag2—O4—S2178.7 (2)
N1—C24—C25—C30−166.4 (3)Ag1—O1—S1—O2−24.1 (4)
C31—C24—C25—C3015.6 (5)Ag1—O1—S1—O3−163.4 (2)
N1—C24—C25—C2616.2 (5)Ag1—O1—S1—C3888.7 (3)
C31—C24—C25—C26−161.8 (3)F1—C38—S1—O2−178.9 (7)
C30—C25—C26—C272.0 (6)F2—C38—S1—O255.3 (7)
C24—C25—C26—C27179.5 (4)F6—C38—S1—O2−58.0 (6)
C25—C26—C27—C28−2.3 (7)F1—C38—S1—O3−56.2 (7)
C26—C27—C28—C290.5 (7)F2—C38—S1—O3178.0 (6)
C27—C28—C29—C301.3 (7)F6—C38—S1—O364.6 (6)
C28—C29—C30—C25−1.5 (7)F1—C38—S1—O160.9 (7)
C26—C25—C30—C29−0.2 (6)F2—C38—S1—O1−64.9 (6)
C24—C25—C30—C29−177.8 (4)F6—C38—S1—O1−178.2 (5)
N1—C24—C31—N594.2 (4)Ag2—O4—S2—O6−40.0 (3)
C25—C24—C31—N5−87.6 (4)Ag2—O4—S2—O5−175.0 (2)
N1—C24—C31—C32−90.0 (4)Ag2—O4—S2—C2373.3 (3)
C25—C24—C31—C3288.2 (4)F4—C23—S2—O6−178.6 (4)
N5—C31—C32—C35147.9 (4)F3—C23—S2—O6−60.7 (5)
C24—C31—C32—C35−27.9 (5)F5—C23—S2—O660.9 (5)
N5—C31—C32—C33−33.7 (5)F4—C23—S2—O5−59.2 (5)
C24—C31—C32—C33150.5 (3)F3—C23—S2—O558.8 (5)
C35—C32—C33—C34−3.6 (6)F5—C23—S2—O5−179.6 (5)
C31—C32—C33—C34178.0 (3)F4—C23—S2—O460.7 (5)
C32—C33—C34—C371.7 (6)F3—C23—S2—O4178.6 (5)
C33—C32—C35—C363.3 (6)F5—C23—S2—O4−59.7 (5)
Symmetry codes: (i) x+1/2, −y+1/2, z+1/2; (ii) x−1/2, −y+1/2, z−1/2.
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C33—H33···O6i0.932.573.486 (5)168
C26—H26···O3iii0.932.523.406 (5)159
C22—H22···O5i0.932.563.382 (4)148
C6—H6···O5iv0.932.473.178 (4)133
Symmetry codes: (i) x+1/2, −y+1/2, z+1/2; (iii) x−1, y, z; (iv) x−1/2, −y+1/2, z+1/2.
Table 1
Selected geometric parameters (Å, °) top
Ag1—N4i2.196 (3)Ag2—N3ii2.169 (3)
Ag1—N52.249 (3)Ag2—N12.217 (3)
Ag1—O12.568 (3)Ag2—O42.592 (3)
N4i—Ag1—N5165.35 (12)N3ii—Ag2—N1157.73 (13)
N4i—Ag1—O185.26 (13)N3ii—Ag2—O494.85 (11)
N5—Ag1—O1108.59 (11)N1—Ag2—O4103.97 (10)
Symmetry codes: (i) x+1/2, −y+1/2, z+1/2; (ii) x−1/2, −y+1/2, z−1/2.
Table 2
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C33—H33···O6i0.932.573.486 (5)168
C26—H26···O3iii0.932.523.406 (5)159
C22—H22···O5i0.932.563.382 (4)148
C6—H6···O5iv0.932.473.178 (4)133
Symmetry codes: (i) x+1/2, −y+1/2, z+1/2; (iii) x−1, y, z; (iv) x−1/2, −y+1/2, z+1/2.
references
References top

Bruker (1997). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.

Liu, L.-D. (2008). Acta Cryst. E64, m363.

Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.

Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.