Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536812050155/yk2079sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536812050155/yk2079Isup2.hkl |
CCDC reference: 899255
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.007 Å
- Disorder in solvent or counterion
- R factor = 0.046
- wR factor = 0.145
- Data-to-parameter ratio = 15.1
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 2.16 PLAT230_ALERT_2_C Hirshfeld Test Diff for C25 -- C26 .. 6.3 su PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Ag1 -- S1 .. 5.6 su PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Ag1 -- S3_a .. 5.8 su PLAT234_ALERT_4_C Large Hirshfeld Difference C31 -- C32 .. 0.16 Ang. PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C30 PLAT906_ALERT_3_C Large K value in the Analysis of Variance ...... 2.192 PLAT910_ALERT_3_C Missing # of FCF Reflections Below Th(Min) ..... 4 PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L= 0.595 68 PLAT913_ALERT_3_C Missing # of Very Strong Reflections in FCF .... 3 PLAT975_ALERT_2_C Positive Residual Density at 0.92A from O6 . 0.68 eA-3 PLAT975_ALERT_2_C Positive Residual Density at 0.69A from O6 . 0.68 eA-3
Alert level G PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite 2 PLAT003_ALERT_2_G Number of Uiso or Uij Restrained Atom Sites .... 12 PLAT005_ALERT_5_G No _iucr_refine_instructions_details in the CIF ? PLAT007_ALERT_5_G Note: Number of Unrefined D-H Atoms ............ 9 PLAT042_ALERT_1_G Calc. and Reported MoietyFormula Strings Differ ? PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature 293 K PLAT244_ALERT_4_G Low 'Solvent' Ueq as Compared to Neighbors of N10 PLAT244_ALERT_4_G Low 'Solvent' Ueq as Compared to Neighbors of N11 PLAT244_ALERT_4_G Low 'Solvent' Ueq as Compared to Neighbors of N12 PLAT244_ALERT_4_G Low 'Solvent' Ueq as Compared to Neighbors of N13 PLAT302_ALERT_4_G Note: Anion/Solvent Disorder ................... 100 Perc. PLAT335_ALERT_2_G Check Large C6 Ring C-C Range C25 -C34 0.15 Ang. PLAT335_ALERT_2_G Check Large C6 Ring C-C Range C28 -C33 0.19 Ang. PLAT380_ALERT_4_G Check Incorrectly? Oriented X(sp2)-Methyl Moiety C43 PLAT380_ALERT_4_G Check Incorrectly? Oriented X(sp2)-Methyl Moiety C44 PLAT380_ALERT_4_G Check Incorrectly? Oriented X(sp2)-Methyl Moiety C46 PLAT380_ALERT_4_G Check Incorrectly? Oriented X(sp2)-Methyl Moiety C47 PLAT764_ALERT_4_G Overcomplete CIF Bond List Detected (Rep/Expd) . 1.10 Ratio PLAT811_ALERT_5_G No ADDSYM Analysis: Too Many Excluded Atoms .... ! PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 63 PLAT909_ALERT_3_G Percentage of Observed Data at Theta(Max) still 57 Perc. PLAT961_ALERT_5_G Dataset Contains no Negative Intensities ....... !
0 ALERT level A = Most likely a serious problem - resolve or explain 0 ALERT level B = A potentially serious problem, consider carefully 12 ALERT level C = Check. Ensure it is not caused by an omission or oversight 23 ALERT level G = General information/check it is not something unexpected 3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 11 ALERT type 2 Indicator that the structure model may be wrong or deficient 6 ALERT type 3 Indicator that the structure quality may be low 11 ALERT type 4 Improvement, methodology, query or suggestion 4 ALERT type 5 Informative message, check
Triethylamine (25 µL, 0.175 mmol) was added to a solution of L5 (0.175 mmol, 0.043 g) in 3 ml DMF. After stirring for 30 min, a DMF solution (2 ml) of AgNO3 (0.175 mmol, 0.030 g) was added. Block yellow crystals were formed by standing the solution in air for two months. Anal. Calcd for C84H88Ag6N22O10S6: C, 41.9; H, 3.7; N, 12.8. Found: C, 41.9; H, 3.6; N, 12.8.
In the compound, all the DMF molecules were found to be disordered, and the s.o.f. for the four disordered molecules were fixed at 0.5. All of the non-hydrogen atoms were refined with anisotropic thermal displacement parameters. The H atoms were placed in calculated positions using the riding model approximation with C—H distances of 0.93–0.96 Å, O—H distances of 0.82 Å and N—H distances of 0.86 Å. Uiso(H) were set to 1.2Ueq (C, N) or 1.5Ueq(C, O).
Transition metal-chalcogen compounds, especially for d10 metal complexes, have attracted a great deal of attention for their interesting structures and excellent luminescent properties (Brito et al., 2011; Forward et al., 1995). Of which many coordination complexes with thiosemicarbazone Schiff base ligands have been reported (Ashfield et al., 2004; Castiñeiras & Pedrido, 2009; Li et al., 2010; Onodera et al., 2007; Pedrido et al., 2009). As a part of our studies on this class of compounds (Sun, 2011; Sun et al., 2012; Sun & Chai, 2012; Xu et al., 2011), we describe here the structure of the title compound.
The structure of the title compound is shown in Fig. 1. It contains an Ag6 hexanuclear cluster with the Ag···Ag distances varying from 2.93 Å to 3.40 Å (Fig. 2), which is shorter than the sum of van der Waals radii of two silver atoms (3.44 Å) (Han et al., 2004). In the cluster, each Ag(I) ion is surrounded by one nitrogen atom and two thiolate sulfur atoms from two deprotonated ligands L5. Each ligand coordinates to three Ag(I) ions using a bridged thiolate sulfur atom and a monodentate nitrogen atom, from which two Ag3S3 hexagonal rings are linked together to give the overall Ferris wheel structure.
There are intramolecular hydrogen bonds of O—H···N type. Besides this, solvent DMF molecules are linked to the hexanuclear cluster via O···H—N hydrogen bonds.
Packing of the title compound (Fig. 3) is facilitated through π–π stacking interactions between aromatic rings I, II [defined by the atoms C(1), C(2), C(3), C(4), C(9) and C(10) and the atoms C(13), C(14), C(15), C(16), C(21) and C(22), respectively] and the symmetry related ones (ring centroid distances: 3.78 Å and 3.70 Å, respectively).
For the structure and luminescent properties of d10 metal complexes, see: Brito et al. (2011); Forward et al. (1995). For structures of related compexes with thiosemicarbazone Schiff base ligands, see: Ashfield et al. (2004); Castiñeiras & Pedrido (2009); Li et al. (2010); Onodera et al. (2007); Pedrido et al. (2009); Sun (2011); Sun et al. (2012); Sun & Chai (2012); Xu et al. (2011). For bond-length data, see: Han et al. (2004).
Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); 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).
[Ag6(C12H10N3OS)6]·4C3H7NO | F(000) = 4816 |
Mr = 2405.34 | Dx = 1.391 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -C 2yc | Cell parameters from 6309 reflections |
a = 24.604 (3) Å | θ = 2.2–27.2° |
b = 18.877 (3) Å | µ = 1.17 mm−1 |
c = 24.816 (3) Å | T = 293 K |
β = 94.763 (3)° | Block, yellow |
V = 11486 (3) Å3 | 0.22 × 0.20 × 0.18 mm |
Z = 4 |
Bruker SMART CCD diffractometer | 10056 independent reflections |
Radiation source: fine-focus sealed tube | 7829 reflections with I > 2s(I) |
Graphite monochromator | Rint = 0.042 |
φ and ω scans | θmax = 25.0°, θmin = 1.7° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −28→29 |
Tmin = 0.238, Tmax = 0.373 | k = −22→21 |
28454 measured reflections | l = −29→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)] = 0.046 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.145 | H-atom parameters constrained |
S = 1.08 | w = 1/[σ2(Fo2) + (0.095P)2] where P = (Fo2 + 2Fc2)/3 |
10056 reflections | (Δ/σ)max = 0.002 |
667 parameters | Δρmax = 0.92 e Å−3 |
63 restraints | Δρmin = −0.42 e Å−3 |
[Ag6(C12H10N3OS)6]·4C3H7NO | V = 11486 (3) Å3 |
Mr = 2405.34 | Z = 4 |
Monoclinic, C2/c | Mo Kα radiation |
a = 24.604 (3) Å | µ = 1.17 mm−1 |
b = 18.877 (3) Å | T = 293 K |
c = 24.816 (3) Å | 0.22 × 0.20 × 0.18 mm |
β = 94.763 (3)° |
Bruker SMART CCD diffractometer | 10056 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 7829 reflections with I > 2s(I) |
Tmin = 0.238, Tmax = 0.373 | Rint = 0.042 |
28454 measured reflections |
R[F2 > 2σ(F2)] = 0.046 | 63 restraints |
wR(F2) = 0.145 | H-atom parameters constrained |
S = 1.08 | Δρmax = 0.92 e Å−3 |
10056 reflections | Δρmin = −0.42 e Å−3 |
667 parameters |
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. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
Ag1 | 0.171626 (12) | 0.813538 (16) | 0.482106 (12) | 0.05265 (8) | |
Ag2 | 0.240712 (12) | 0.788788 (17) | 0.582419 (12) | 0.05635 (9) | |
Ag3 | 0.191030 (13) | 0.661685 (16) | 0.509778 (12) | 0.05414 (8) | |
S1 | 0.16540 (4) | 0.75257 (5) | 0.39220 (4) | 0.0510 (2) | |
S2 | 0.16228 (4) | 0.70906 (5) | 0.59592 (4) | 0.0520 (2) | |
S3 | 0.27035 (4) | 0.57841 (5) | 0.51287 (4) | 0.0499 (2) | |
N1 | 0.09822 (14) | 0.57526 (18) | 0.43441 (14) | 0.0591 (9) | |
N2 | 0.13114 (13) | 0.63483 (17) | 0.43751 (13) | 0.0531 (8) | |
N3 | 0.08875 (19) | 0.6661 (3) | 0.35352 (18) | 0.0993 (14) | |
H3A | 0.0673 | 0.6301 | 0.3527 | 0.119* | |
H3B | 0.0868 | 0.6956 | 0.3271 | 0.119* | |
N4 | 0.05033 (12) | 0.83205 (16) | 0.52337 (13) | 0.0475 (8) | |
N5 | 0.10008 (12) | 0.79779 (16) | 0.53377 (12) | 0.0476 (8) | |
N6 | 0.06729 (14) | 0.76102 (19) | 0.61488 (13) | 0.0614 (9) | |
H6A | 0.0380 | 0.7858 | 0.6092 | 0.074* | |
H6B | 0.0725 | 0.7360 | 0.6438 | 0.074* | |
N7 | 0.27039 (15) | 0.5619 (2) | 0.35485 (14) | 0.0656 (10) | |
N8 | 0.27440 (14) | 0.59230 (18) | 0.40692 (12) | 0.0575 (9) | |
N9 | 0.25925 (15) | 0.47922 (19) | 0.43895 (15) | 0.0671 (10) | |
H9A | 0.2586 | 0.4610 | 0.4071 | 0.080* | |
H9B | 0.2547 | 0.4527 | 0.4664 | 0.080* | |
O1 | 0.02497 (15) | 0.48899 (18) | 0.39190 (13) | 0.0853 (10) | |
H1B | 0.0463 | 0.5224 | 0.3930 | 0.128* | |
O2 | −0.05009 (11) | 0.86290 (17) | 0.53609 (12) | 0.0686 (8) | |
H2B | −0.0209 | 0.8420 | 0.5413 | 0.103* | |
O3 | 0.2174 (2) | 0.4973 (3) | 0.27494 (18) | 0.1230 (16) | |
H3C | 0.2245 | 0.5096 | 0.3064 | 0.184* | |
C1 | 0.0316 (2) | 0.4524 (2) | 0.4389 (2) | 0.0696 (12) | |
C2 | −0.0022 (2) | 0.3926 (3) | 0.4433 (2) | 0.0858 (16) | |
H2A | −0.0264 | 0.3788 | 0.4144 | 0.103* | |
C3 | 0.0012 (2) | 0.3550 (3) | 0.4907 (2) | 0.0824 (15) | |
H3D | −0.0213 | 0.3157 | 0.4936 | 0.099* | |
C4 | 0.0369 (2) | 0.3736 (2) | 0.5340 (2) | 0.0710 (13) | |
C5 | 0.0388 (3) | 0.3357 (3) | 0.5855 (3) | 0.0961 (18) | |
H5A | 0.0155 | 0.2975 | 0.5892 | 0.115* | |
C6 | 0.0736 (3) | 0.3551 (3) | 0.6272 (3) | 0.109 (2) | |
H6C | 0.0739 | 0.3303 | 0.6596 | 0.131* | |
C7 | 0.1083 (3) | 0.4100 (3) | 0.6233 (2) | 0.104 (2) | |
H7B | 0.1324 | 0.4220 | 0.6527 | 0.125* | |
C8 | 0.1084 (2) | 0.4484 (3) | 0.5761 (2) | 0.0873 (16) | |
H8B | 0.1330 | 0.4856 | 0.5742 | 0.105* | |
C9 | 0.07184 (19) | 0.4329 (2) | 0.53019 (19) | 0.0678 (12) | |
C10 | 0.06846 (18) | 0.4728 (2) | 0.48118 (18) | 0.0633 (11) | |
C11 | 0.10170 (17) | 0.5363 (2) | 0.47600 (18) | 0.0600 (11) | |
H11A | 0.1266 | 0.5487 | 0.5047 | 0.072* | |
C12 | 0.12505 (16) | 0.6761 (2) | 0.39585 (16) | 0.0529 (10) | |
C13 | −0.04809 (15) | 0.9071 (2) | 0.49380 (17) | 0.0547 (10) | |
C14 | −0.09473 (17) | 0.9478 (2) | 0.47924 (19) | 0.0659 (12) | |
H14A | −0.1254 | 0.9428 | 0.4984 | 0.079* | |
C15 | −0.09576 (17) | 0.9941 (3) | 0.4380 (2) | 0.0671 (12) | |
H15A | −0.1271 | 1.0207 | 0.4294 | 0.080* | |
C16 | −0.05039 (17) | 1.0030 (2) | 0.40773 (17) | 0.0602 (11) | |
C17 | −0.0514 (2) | 1.0516 (3) | 0.36387 (19) | 0.0711 (13) | |
H17A | −0.0823 | 1.0790 | 0.3556 | 0.085* | |
C18 | −0.0087 (2) | 1.0587 (3) | 0.3344 (2) | 0.0818 (15) | |
H18A | −0.0103 | 1.0906 | 0.3058 | 0.098* | |
C19 | 0.0376 (2) | 1.0188 (3) | 0.3463 (2) | 0.0780 (14) | |
H19A | 0.0667 | 1.0235 | 0.3249 | 0.094* | |
C20 | 0.04169 (19) | 0.9720 (2) | 0.38905 (18) | 0.0654 (12) | |
H20A | 0.0739 | 0.9468 | 0.3968 | 0.078* | |
C21 | −0.00225 (15) | 0.9620 (2) | 0.42120 (16) | 0.0521 (10) | |
C22 | −0.00177 (15) | 0.9137 (2) | 0.46551 (15) | 0.0497 (9) | |
C23 | 0.04720 (15) | 0.87334 (19) | 0.48270 (15) | 0.0484 (9) | |
H23A | 0.0776 | 0.8780 | 0.4630 | 0.058* | |
C24 | 0.10444 (14) | 0.76144 (19) | 0.57889 (14) | 0.0435 (8) | |
C25 | 0.2510 (3) | 0.5314 (4) | 0.2427 (2) | 0.104 (2) | |
C26 | 0.2459 (3) | 0.5160 (4) | 0.1857 (3) | 0.1147 (18) | |
H26A | 0.2203 | 0.4836 | 0.1712 | 0.138* | |
C27 | 0.2789 (3) | 0.5496 (4) | 0.1544 (3) | 0.1144 (18) | |
H27A | 0.2745 | 0.5391 | 0.1177 | 0.137* | |
C28 | 0.3180 (3) | 0.5973 (3) | 0.1699 (2) | 0.0934 (15) | |
C29 | 0.3531 (3) | 0.6318 (4) | 0.1345 (2) | 0.1046 (18) | |
H29A | 0.3493 | 0.6213 | 0.0977 | 0.126* | |
C30 | 0.3886 (3) | 0.6755 (4) | 0.1515 (3) | 0.127 (2) | |
H30A | 0.4086 | 0.6988 | 0.1268 | 0.152* | |
C31 | 0.3996 (3) | 0.6910 (4) | 0.2081 (3) | 0.114 (2) | |
H31A | 0.4273 | 0.7223 | 0.2199 | 0.137* | |
C32 | 0.3687 (3) | 0.6590 (3) | 0.2442 (2) | 0.1015 (19) | |
H32A | 0.3757 | 0.6680 | 0.2809 | 0.122* | |
C33 | 0.3264 (2) | 0.6125 (3) | 0.2266 (2) | 0.0911 (16) | |
C34 | 0.2898 (2) | 0.5779 (3) | 0.26316 (19) | 0.0814 (15) | |
C35 | 0.29397 (18) | 0.5973 (3) | 0.32006 (16) | 0.0645 (12) | |
H35A | 0.3145 | 0.6368 | 0.3313 | 0.077* | |
C36 | 0.26717 (15) | 0.5477 (2) | 0.44566 (15) | 0.0488 (9) | |
C37 | 0.1231 (5) | 0.9297 (5) | 0.2325 (5) | 0.087 (3) | 0.50 |
H37A | 0.1419 | 0.9325 | 0.2679 | 0.130* | 0.50 |
H37B | 0.0973 | 0.9678 | 0.2277 | 0.130* | 0.50 |
H37C | 0.1489 | 0.9331 | 0.2056 | 0.130* | 0.50 |
C38 | 0.0619 (5) | 0.8437 (6) | 0.1746 (5) | 0.089 (3) | 0.50 |
H38A | 0.0455 | 0.7980 | 0.1785 | 0.133* | 0.50 |
H38B | 0.0854 | 0.8423 | 0.1456 | 0.133* | 0.50 |
H38C | 0.0338 | 0.8784 | 0.1667 | 0.133* | 0.50 |
C39 | 0.0960 (4) | 0.8193 (6) | 0.2672 (4) | 0.078 (3) | 0.50 |
H39A | 0.1113 | 0.8342 | 0.3008 | 0.093* | 0.50 |
N10 | 0.0949 (3) | 0.8634 (3) | 0.2267 (3) | 0.0561 (17) | 0.50 |
O4 | 0.0773 (3) | 0.7578 (4) | 0.2628 (3) | 0.095 (2) | 0.50 |
C40 | 0.2559 (5) | 0.7879 (6) | 0.2711 (4) | 0.087 (3) | 0.50 |
H40A | 0.2754 | 0.8308 | 0.2806 | 0.130* | 0.50 |
H40B | 0.2801 | 0.7482 | 0.2767 | 0.130* | 0.50 |
H40C | 0.2260 | 0.7828 | 0.2932 | 0.130* | 0.50 |
C41 | 0.2129 (6) | 0.7401 (7) | 0.2012 (6) | 0.161 (6) | 0.50 |
H41A | 0.2007 | 0.7454 | 0.1636 | 0.242* | 0.50 |
H41B | 0.1820 | 0.7328 | 0.2217 | 0.242* | 0.50 |
H41C | 0.2369 | 0.7001 | 0.2057 | 0.242* | 0.50 |
C42 | 0.2428 (7) | 0.8450 (8) | 0.1807 (6) | 0.125 (5) | 0.50 |
H42A | 0.2656 | 0.8799 | 0.1965 | 0.150* | 0.50 |
N11 | 0.2359 (3) | 0.7908 (4) | 0.2164 (3) | 0.0563 (18) | 0.50 |
O5 | 0.2296 (5) | 0.8580 (5) | 0.1406 (3) | 0.136 (4) | 0.50 |
O6 | 0.4334 (3) | 0.8328 (4) | 0.2955 (3) | 0.090 (2) | 0.50 |
C43 | 0.4240 (4) | 1.0056 (5) | 0.2406 (4) | 0.081 (3) | 0.50 |
H43A | 0.4350 | 1.0254 | 0.2754 | 0.121* | 0.50 |
H43B | 0.3889 | 1.0239 | 0.2279 | 0.121* | 0.50 |
H43C | 0.4502 | 1.0180 | 0.2155 | 0.121* | 0.50 |
C44 | 0.4052 (4) | 0.8921 (6) | 0.1971 (4) | 0.084 (3) | 0.50 |
H44A | 0.4048 | 0.8424 | 0.2051 | 0.126* | 0.50 |
H44B | 0.4307 | 0.9012 | 0.1707 | 0.126* | 0.50 |
H44C | 0.3694 | 0.9069 | 0.1832 | 0.126* | 0.50 |
C45 | 0.4319 (4) | 0.8969 (7) | 0.2912 (5) | 0.089 (3) | 0.50 |
H45A | 0.4389 | 0.9239 | 0.3224 | 0.107* | 0.50 |
N12 | 0.4210 (3) | 0.9304 (4) | 0.2449 (2) | 0.063 (2) | 0.50 |
O7 | 0.2454 (2) | 0.3792 (3) | 0.5239 (2) | 0.0587 (13) | 0.50 |
C46 | 0.1547 (4) | 0.2320 (4) | 0.5242 (4) | 0.075 (3) | 0.50 |
H46A | 0.1703 | 0.2201 | 0.5598 | 0.112* | 0.50 |
H46B | 0.1600 | 0.1934 | 0.5000 | 0.112* | 0.50 |
H46C | 0.1164 | 0.2410 | 0.5252 | 0.112* | 0.50 |
C47 | 0.1648 (4) | 0.3228 (5) | 0.4527 (4) | 0.073 (3) | 0.50 |
H47A | 0.1858 | 0.3643 | 0.4461 | 0.109* | 0.50 |
H47B | 0.1268 | 0.3351 | 0.4510 | 0.109* | 0.50 |
H47C | 0.1704 | 0.2876 | 0.4259 | 0.109* | 0.50 |
C48 | 0.2207 (4) | 0.3293 (4) | 0.5356 (3) | 0.060 (2) | 0.50 |
H48A | 0.2294 | 0.3111 | 0.5701 | 0.072* | 0.50 |
N13 | 0.1815 (3) | 0.2954 (3) | 0.5052 (3) | 0.0468 (15) | 0.50 |
U11 | U22 | U33 | U12 | U13 | U23 | |
Ag1 | 0.05776 (17) | 0.05486 (17) | 0.04597 (16) | −0.00022 (13) | 0.00805 (13) | 0.00734 (12) |
Ag2 | 0.05578 (17) | 0.06027 (18) | 0.05285 (18) | 0.00050 (13) | 0.00367 (14) | 0.00891 (13) |
Ag3 | 0.06226 (18) | 0.05244 (17) | 0.04791 (17) | 0.00372 (13) | 0.00561 (14) | 0.00294 (12) |
S1 | 0.0549 (5) | 0.0543 (5) | 0.0438 (5) | −0.0023 (4) | 0.0035 (4) | 0.0061 (4) |
S2 | 0.0564 (5) | 0.0552 (5) | 0.0450 (5) | 0.0023 (4) | 0.0079 (4) | 0.0091 (4) |
S3 | 0.0570 (5) | 0.0488 (5) | 0.0446 (5) | 0.0013 (4) | 0.0081 (4) | 0.0031 (4) |
N1 | 0.0648 (19) | 0.0566 (19) | 0.0556 (19) | −0.0095 (16) | 0.0042 (16) | 0.0038 (16) |
N2 | 0.0554 (17) | 0.0538 (18) | 0.0497 (18) | −0.0064 (15) | 0.0017 (14) | 0.0065 (15) |
N3 | 0.109 (3) | 0.098 (3) | 0.085 (3) | −0.033 (2) | −0.027 (2) | 0.016 (2) |
N4 | 0.0439 (15) | 0.0487 (17) | 0.0504 (17) | 0.0009 (13) | 0.0069 (13) | 0.0001 (14) |
N5 | 0.0439 (15) | 0.0514 (17) | 0.0480 (17) | 0.0004 (13) | 0.0064 (13) | 0.0060 (13) |
N6 | 0.0601 (19) | 0.073 (2) | 0.0532 (19) | 0.0072 (17) | 0.0165 (16) | 0.0100 (16) |
N7 | 0.079 (2) | 0.068 (2) | 0.0490 (19) | 0.0157 (18) | 0.0009 (17) | −0.0046 (17) |
N8 | 0.071 (2) | 0.063 (2) | 0.0390 (17) | 0.0076 (17) | 0.0063 (15) | 0.0032 (15) |
N9 | 0.091 (3) | 0.057 (2) | 0.054 (2) | −0.0044 (18) | 0.0069 (18) | −0.0029 (16) |
O1 | 0.116 (3) | 0.073 (2) | 0.0638 (19) | −0.0227 (19) | −0.0104 (18) | −0.0023 (16) |
O2 | 0.0522 (15) | 0.084 (2) | 0.0713 (19) | 0.0015 (15) | 0.0128 (14) | 0.0191 (16) |
O3 | 0.131 (3) | 0.137 (4) | 0.095 (3) | −0.006 (3) | −0.029 (3) | −0.024 (3) |
C1 | 0.082 (3) | 0.057 (2) | 0.070 (3) | −0.012 (2) | 0.007 (2) | −0.005 (2) |
C2 | 0.105 (4) | 0.064 (3) | 0.086 (4) | −0.028 (3) | −0.005 (3) | −0.007 (3) |
C3 | 0.093 (3) | 0.056 (3) | 0.099 (4) | −0.024 (2) | 0.011 (3) | −0.001 (3) |
C4 | 0.081 (3) | 0.053 (2) | 0.080 (3) | −0.011 (2) | 0.012 (2) | 0.006 (2) |
C5 | 0.110 (4) | 0.067 (3) | 0.112 (5) | −0.018 (3) | 0.013 (4) | 0.020 (3) |
C6 | 0.135 (5) | 0.097 (4) | 0.095 (4) | −0.015 (4) | 0.008 (4) | 0.041 (3) |
C7 | 0.127 (5) | 0.093 (4) | 0.088 (4) | −0.028 (4) | −0.022 (3) | 0.032 (3) |
C8 | 0.093 (3) | 0.075 (3) | 0.091 (4) | −0.023 (3) | −0.010 (3) | 0.019 (3) |
C9 | 0.073 (3) | 0.056 (2) | 0.075 (3) | −0.005 (2) | 0.004 (2) | 0.007 (2) |
C10 | 0.073 (3) | 0.054 (2) | 0.063 (3) | −0.012 (2) | 0.008 (2) | 0.0020 (19) |
C11 | 0.063 (2) | 0.057 (2) | 0.059 (2) | −0.0090 (19) | 0.000 (2) | −0.001 (2) |
C12 | 0.057 (2) | 0.053 (2) | 0.047 (2) | −0.0052 (17) | −0.0048 (17) | 0.0039 (17) |
C13 | 0.048 (2) | 0.057 (2) | 0.058 (2) | −0.0037 (18) | 0.0050 (18) | −0.0016 (18) |
C14 | 0.047 (2) | 0.071 (3) | 0.080 (3) | 0.001 (2) | 0.010 (2) | −0.001 (2) |
C15 | 0.050 (2) | 0.069 (3) | 0.081 (3) | 0.011 (2) | −0.001 (2) | −0.007 (2) |
C16 | 0.064 (2) | 0.052 (2) | 0.061 (2) | 0.0017 (19) | −0.011 (2) | −0.0077 (19) |
C17 | 0.075 (3) | 0.064 (3) | 0.072 (3) | 0.004 (2) | −0.011 (2) | 0.008 (2) |
C18 | 0.106 (4) | 0.068 (3) | 0.069 (3) | 0.001 (3) | −0.005 (3) | 0.019 (2) |
C19 | 0.091 (3) | 0.079 (3) | 0.064 (3) | −0.003 (3) | 0.013 (3) | 0.013 (2) |
C20 | 0.070 (3) | 0.067 (3) | 0.060 (3) | 0.003 (2) | 0.012 (2) | 0.006 (2) |
C21 | 0.054 (2) | 0.048 (2) | 0.053 (2) | −0.0029 (17) | 0.0006 (17) | −0.0022 (17) |
C22 | 0.050 (2) | 0.048 (2) | 0.050 (2) | −0.0012 (16) | −0.0007 (16) | −0.0053 (16) |
C23 | 0.0459 (18) | 0.047 (2) | 0.053 (2) | 0.0008 (16) | 0.0070 (16) | −0.0009 (17) |
C24 | 0.0447 (17) | 0.0476 (19) | 0.0386 (18) | −0.0071 (15) | 0.0062 (15) | −0.0008 (15) |
C25 | 0.123 (5) | 0.123 (5) | 0.060 (3) | 0.036 (4) | −0.021 (3) | −0.018 (3) |
C26 | 0.119 (3) | 0.127 (5) | 0.093 (4) | 0.025 (3) | −0.021 (2) | −0.002 (3) |
C27 | 0.131 (3) | 0.117 (3) | 0.093 (3) | 0.036 (3) | −0.002 (2) | −0.010 (3) |
C28 | 0.109 (3) | 0.105 (3) | 0.0665 (12) | 0.033 (3) | 0.009 (2) | 0.005 (2) |
C29 | 0.126 (3) | 0.119 (3) | 0.072 (3) | 0.026 (3) | 0.022 (3) | 0.007 (3) |
C30 | 0.137 (4) | 0.138 (4) | 0.109 (4) | 0.021 (3) | 0.032 (3) | 0.022 (3) |
C31 | 0.123 (4) | 0.118 (4) | 0.103 (3) | 0.020 (3) | 0.025 (3) | 0.017 (3) |
C32 | 0.126 (4) | 0.108 (4) | 0.076 (3) | 0.045 (4) | 0.043 (3) | 0.030 (3) |
C33 | 0.116 (4) | 0.105 (4) | 0.0553 (15) | 0.061 (3) | 0.026 (2) | 0.022 (2) |
C34 | 0.105 (3) | 0.088 (3) | 0.050 (3) | 0.045 (3) | 0.000 (2) | 0.002 (2) |
C35 | 0.080 (3) | 0.072 (3) | 0.042 (2) | 0.021 (2) | 0.006 (2) | 0.0029 (19) |
C36 | 0.0509 (19) | 0.048 (2) | 0.047 (2) | 0.0081 (16) | 0.0000 (16) | −0.0023 (16) |
C37 | 0.098 (7) | 0.069 (6) | 0.091 (7) | −0.002 (5) | −0.009 (6) | 0.005 (5) |
C38 | 0.104 (4) | 0.079 (4) | 0.081 (4) | 0.007 (3) | −0.013 (4) | 0.012 (3) |
C39 | 0.091 (7) | 0.082 (6) | 0.056 (5) | 0.006 (5) | −0.024 (5) | 0.014 (5) |
N10 | 0.071 (4) | 0.037 (3) | 0.057 (4) | 0.015 (3) | −0.020 (3) | 0.011 (3) |
O4 | 0.105 (4) | 0.095 (4) | 0.078 (3) | −0.016 (3) | −0.027 (3) | 0.037 (3) |
C40 | 0.116 (8) | 0.080 (7) | 0.063 (6) | 0.031 (6) | −0.002 (6) | −0.007 (5) |
C41 | 0.162 (12) | 0.139 (11) | 0.189 (15) | 0.098 (9) | 0.052 (11) | 0.082 (10) |
C42 | 0.157 (12) | 0.105 (10) | 0.112 (11) | −0.033 (9) | 0.004 (10) | −0.007 (8) |
N11 | 0.079 (4) | 0.050 (4) | 0.041 (3) | 0.008 (3) | 0.015 (3) | 0.004 (3) |
O5 | 0.222 (10) | 0.130 (6) | 0.054 (4) | −0.029 (7) | −0.002 (5) | 0.058 (4) |
O6 | 0.115 (5) | 0.103 (5) | 0.055 (3) | 0.005 (4) | 0.030 (3) | 0.049 (3) |
C43 | 0.086 (6) | 0.071 (6) | 0.084 (7) | −0.016 (5) | −0.003 (5) | 0.017 (5) |
C44 | 0.092 (7) | 0.084 (7) | 0.076 (6) | −0.011 (5) | 0.004 (5) | 0.033 (5) |
C45 | 0.082 (4) | 0.104 (5) | 0.082 (4) | 0.000 (4) | 0.014 (3) | 0.004 (4) |
N12 | 0.049 (3) | 0.103 (5) | 0.038 (3) | 0.001 (4) | 0.000 (3) | 0.029 (3) |
O7 | 0.086 (3) | 0.049 (2) | 0.038 (2) | −0.033 (2) | −0.010 (2) | 0.0095 (19) |
C46 | 0.081 (6) | 0.048 (5) | 0.096 (7) | −0.031 (4) | 0.010 (5) | 0.001 (5) |
C47 | 0.078 (6) | 0.060 (5) | 0.076 (6) | −0.007 (4) | −0.024 (5) | −0.009 (4) |
C48 | 0.101 (6) | 0.051 (4) | 0.025 (3) | −0.008 (4) | −0.005 (4) | 0.007 (3) |
N13 | 0.058 (3) | 0.031 (3) | 0.050 (4) | −0.010 (3) | 0.002 (3) | −0.009 (2) |
Ag1—N5 | 2.282 (3) | C18—C19 | 1.377 (7) |
Ag1—S3i | 2.4869 (10) | C18—H18A | 0.9300 |
Ag1—S1 | 2.5039 (10) | C19—C20 | 1.378 (6) |
Ag1—Ag2 | 2.9329 (5) | C19—H19A | 0.9300 |
Ag1—Ag3 | 2.9769 (6) | C20—C21 | 1.409 (6) |
Ag2—N8i | 2.294 (3) | C20—H20A | 0.9300 |
Ag2—S1i | 2.4699 (10) | C21—C22 | 1.428 (5) |
Ag2—S2 | 2.4917 (11) | C22—C23 | 1.459 (5) |
Ag2—Ag3i | 3.0931 (5) | C23—H23A | 0.9300 |
Ag2—Ag3 | 3.1835 (5) | C25—C34 | 1.364 (8) |
Ag3—N2 | 2.282 (3) | C25—C26 | 1.438 (8) |
Ag3—S2 | 2.4741 (11) | C26—C27 | 1.330 (10) |
Ag3—S3 | 2.5020 (10) | C26—H26A | 0.9300 |
Ag3—Ag2i | 3.0931 (5) | C27—C28 | 1.350 (9) |
S1—C12 | 1.759 (4) | C27—H27A | 0.9300 |
S1—Ag2i | 2.4699 (10) | C28—C33 | 1.436 (7) |
S2—C24 | 1.755 (4) | C28—C29 | 1.438 (9) |
S3—C36 | 1.762 (4) | C29—C30 | 1.248 (10) |
S3—Ag1i | 2.4869 (10) | C29—H29A | 0.9300 |
N1—C11 | 1.264 (5) | C30—C31 | 1.438 (10) |
N1—N2 | 1.384 (5) | C30—H30A | 0.9300 |
N2—C12 | 1.293 (5) | C31—C32 | 1.363 (9) |
N3—C12 | 1.335 (6) | C31—H31A | 0.9300 |
N3—H3A | 0.8600 | C32—C33 | 1.403 (9) |
N3—H3B | 0.8600 | C32—H32A | 0.9300 |
N4—C23 | 1.273 (5) | C33—C34 | 1.480 (8) |
N4—N5 | 1.390 (4) | C34—C35 | 1.454 (6) |
N5—C24 | 1.310 (5) | C35—H35A | 0.9300 |
N6—C24 | 1.330 (5) | C37—N10 | 1.432 (12) |
N6—H6A | 0.8600 | C37—H37A | 0.9600 |
N6—H6B | 0.8600 | C37—H37B | 0.9600 |
N7—C35 | 1.270 (6) | C37—H37C | 0.9600 |
N7—N8 | 1.410 (5) | C38—N10 | 1.516 (12) |
N8—C36 | 1.302 (5) | C38—H38A | 0.9600 |
N8—Ag2i | 2.294 (3) | C38—H38B | 0.9600 |
N9—C36 | 1.315 (5) | C38—H38C | 0.9600 |
N9—H9A | 0.8600 | C39—O4 | 1.250 (12) |
N9—H9B | 0.8600 | C39—N10 | 1.302 (11) |
O1—C1 | 1.354 (6) | C39—H39A | 0.9300 |
O1—H1B | 0.8200 | C40—N11 | 1.406 (11) |
O2—C13 | 1.345 (5) | C40—H40A | 0.9600 |
O2—H2B | 0.8200 | C40—H40B | 0.9600 |
O3—C25 | 1.361 (8) | C40—H40C | 0.9600 |
O3—H3C | 0.8200 | C41—N11 | 1.159 (16) |
C1—C10 | 1.384 (6) | C41—H41A | 0.9600 |
C1—C2 | 1.411 (7) | C41—H41B | 0.9600 |
C2—C3 | 1.369 (7) | C41—H41C | 0.9600 |
C2—H2A | 0.9300 | C42—O5 | 1.052 (16) |
C3—C4 | 1.377 (7) | C42—N11 | 1.372 (16) |
C3—H3D | 0.9300 | C42—H42A | 0.9300 |
C4—C9 | 1.419 (6) | O6—C45 | 1.215 (14) |
C4—C5 | 1.461 (8) | C43—N12 | 1.425 (13) |
C5—C6 | 1.340 (9) | C43—H43A | 0.9600 |
C5—H5A | 0.9300 | C43—H43B | 0.9600 |
C6—C7 | 1.352 (8) | C43—H43C | 0.9600 |
C6—H6C | 0.9300 | C44—N12 | 1.415 (13) |
C7—C8 | 1.377 (8) | C44—H44A | 0.9600 |
C7—H7B | 0.9300 | C44—H44B | 0.9600 |
C8—C9 | 1.422 (7) | C44—H44C | 0.9600 |
C8—H8B | 0.9300 | C45—N12 | 1.320 (13) |
C9—C10 | 1.428 (6) | C45—H45A | 0.9300 |
C10—C11 | 1.463 (6) | O7—C48 | 1.171 (10) |
C11—H11A | 0.9300 | C46—N13 | 1.463 (10) |
C13—C22 | 1.393 (5) | C46—H46A | 0.9600 |
C13—C14 | 1.404 (6) | C46—H46B | 0.9600 |
C14—C15 | 1.343 (7) | C46—H46C | 0.9600 |
C14—H14A | 0.9300 | C47—N13 | 1.428 (11) |
C15—C16 | 1.407 (6) | C47—H47A | 0.9600 |
C15—H15A | 0.9300 | C47—H47B | 0.9600 |
C16—C17 | 1.423 (6) | C47—H47C | 0.9600 |
C16—C21 | 1.431 (6) | C48—N13 | 1.338 (10) |
C17—C18 | 1.334 (7) | C48—H48A | 0.9300 |
C17—H17A | 0.9300 | ||
N5—Ag1—S3i | 123.04 (8) | C18—C19—C20 | 121.5 (5) |
N5—Ag1—S1 | 116.61 (8) | C18—C19—H19A | 119.3 |
S3i—Ag1—S1 | 114.45 (3) | C20—C19—H19A | 119.3 |
N5—Ag1—Ag2 | 85.53 (8) | C19—C20—C21 | 120.8 (4) |
S3i—Ag1—Ag2 | 78.36 (2) | C19—C20—H20A | 119.6 |
S1—Ag1—Ag2 | 132.17 (3) | C21—C20—H20A | 119.6 |
N5—Ag1—Ag3 | 82.03 (8) | C20—C21—C22 | 124.4 (4) |
S3i—Ag1—Ag3 | 134.25 (3) | C20—C21—C16 | 117.0 (4) |
S1—Ag1—Ag3 | 76.10 (2) | C22—C21—C16 | 118.6 (4) |
Ag2—Ag1—Ag3 | 65.183 (11) | C13—C22—C21 | 119.4 (3) |
N8i—Ag2—S1i | 115.91 (9) | C13—C22—C23 | 119.8 (3) |
N8i—Ag2—S2 | 116.15 (9) | C21—C22—C23 | 120.8 (3) |
S1i—Ag2—S2 | 119.55 (4) | N4—C23—C22 | 123.1 (3) |
N8i—Ag2—Ag1 | 81.60 (8) | N4—C23—H23A | 118.5 |
S1i—Ag2—Ag1 | 136.94 (3) | C22—C23—H23A | 118.5 |
S2—Ag2—Ag1 | 79.02 (2) | N5—C24—N6 | 124.4 (3) |
N8i—Ag2—Ag3i | 83.84 (8) | N5—C24—S2 | 120.5 (3) |
S1i—Ag2—Ag3i | 74.37 (2) | N6—C24—S2 | 115.1 (3) |
S2—Ag2—Ag3i | 139.12 (3) | O3—C25—C34 | 121.8 (5) |
Ag1—Ag2—Ag3i | 68.654 (13) | O3—C25—C26 | 118.3 (6) |
N8i—Ag2—Ag3 | 138.11 (8) | C34—C25—C26 | 119.9 (6) |
S1i—Ag2—Ag3 | 102.31 (3) | C27—C26—C25 | 118.0 (7) |
S2—Ag2—Ag3 | 49.88 (2) | C27—C26—H26A | 121.0 |
Ag1—Ag2—Ag3 | 58.076 (12) | C25—C26—H26A | 121.0 |
Ag3i—Ag2—Ag3 | 90.886 (14) | C26—C27—C28 | 127.3 (7) |
N2—Ag3—S2 | 123.17 (9) | C26—C27—H27A | 116.3 |
N2—Ag3—S3 | 109.62 (9) | C28—C27—H27A | 116.3 |
S2—Ag3—S3 | 118.61 (3) | C27—C28—C33 | 117.0 (6) |
N2—Ag3—Ag1 | 87.24 (8) | C27—C28—C29 | 125.3 (6) |
S2—Ag3—Ag1 | 78.42 (3) | C33—C28—C29 | 117.7 (6) |
S3—Ag3—Ag1 | 136.20 (3) | C30—C29—C28 | 122.0 (7) |
N2—Ag3—Ag2i | 80.83 (8) | C30—C29—H29A | 119.0 |
S2—Ag3—Ag2i | 137.87 (3) | C28—C29—H29A | 119.0 |
S3—Ag3—Ag2i | 75.09 (2) | C29—C30—C31 | 122.4 (8) |
Ag1—Ag3—Ag2i | 67.966 (11) | C29—C30—H30A | 118.8 |
N2—Ag3—Ag2 | 143.62 (8) | C31—C30—H30A | 118.8 |
S2—Ag3—Ag2 | 50.37 (2) | C32—C31—C30 | 118.7 (7) |
S3—Ag3—Ag2 | 101.20 (3) | C32—C31—H31A | 120.7 |
Ag1—Ag3—Ag2 | 56.741 (12) | C30—C31—H31A | 120.7 |
Ag2i—Ag3—Ag2 | 89.114 (14) | C31—C32—C33 | 120.9 (6) |
C12—S1—Ag2i | 104.32 (14) | C31—C32—H32A | 119.5 |
C12—S1—Ag1 | 108.93 (14) | C33—C32—H32A | 119.5 |
Ag2i—S1—Ag1 | 86.06 (3) | C32—C33—C28 | 118.1 (5) |
C24—S2—Ag3 | 106.25 (12) | C32—C33—C34 | 124.0 (5) |
C24—S2—Ag2 | 104.41 (12) | C28—C33—C34 | 117.9 (6) |
Ag3—S2—Ag2 | 79.74 (3) | C25—C34—C35 | 121.0 (5) |
C36—S3—Ag1i | 107.32 (13) | C25—C34—C33 | 119.8 (5) |
C36—S3—Ag3 | 101.81 (12) | C35—C34—C33 | 119.1 (5) |
Ag1i—S3—Ag3 | 85.95 (3) | N7—C35—C34 | 121.9 (5) |
C11—N1—N2 | 115.3 (3) | N7—C35—H35A | 119.1 |
C12—N2—N1 | 114.6 (3) | C34—C35—H35A | 119.1 |
C12—N2—Ag3 | 121.3 (3) | N8—C36—N9 | 124.8 (4) |
N1—N2—Ag3 | 124.1 (2) | N8—C36—S3 | 119.2 (3) |
C12—N3—H3A | 120.0 | N9—C36—S3 | 116.0 (3) |
C12—N3—H3B | 120.0 | N10—C37—H37A | 109.5 |
H3A—N3—H3B | 120.0 | N10—C37—H37B | 109.5 |
C23—N4—N5 | 115.3 (3) | H37A—C37—H37B | 109.5 |
C24—N5—N4 | 114.3 (3) | N10—C37—H37C | 109.5 |
C24—N5—Ag1 | 122.4 (2) | H37A—C37—H37C | 109.5 |
N4—N5—Ag1 | 122.9 (2) | H37B—C37—H37C | 109.5 |
C24—N6—H6A | 120.0 | N10—C38—H38A | 109.5 |
C24—N6—H6B | 120.0 | N10—C38—H38B | 109.5 |
H6A—N6—H6B | 120.0 | H38A—C38—H38B | 109.5 |
C35—N7—N8 | 114.1 (4) | N10—C38—H38C | 109.5 |
C36—N8—N7 | 114.2 (3) | H38A—C38—H38C | 109.5 |
C36—N8—Ag2i | 121.0 (3) | H38B—C38—H38C | 109.5 |
N7—N8—Ag2i | 120.3 (2) | O4—C39—N10 | 122.9 (9) |
C36—N9—H9A | 120.0 | O4—C39—H39A | 118.5 |
C36—N9—H9B | 120.0 | N10—C39—H39A | 118.5 |
H9A—N9—H9B | 120.0 | C39—N10—C37 | 120.2 (8) |
C1—O1—H1B | 109.5 | C39—N10—C38 | 118.4 (8) |
C13—O2—H2B | 109.5 | C37—N10—C38 | 121.3 (7) |
C25—O3—H3C | 109.5 | N11—C40—H40A | 109.5 |
O1—C1—C10 | 122.3 (4) | N11—C40—H40B | 109.5 |
O1—C1—C2 | 116.5 (4) | H40A—C40—H40B | 109.5 |
C10—C1—C2 | 121.1 (5) | N11—C40—H40C | 109.5 |
C3—C2—C1 | 119.2 (5) | H40A—C40—H40C | 109.5 |
C3—C2—H2A | 120.4 | H40B—C40—H40C | 109.5 |
C1—C2—H2A | 120.4 | N11—C41—H41A | 109.5 |
C2—C3—C4 | 121.7 (5) | N11—C41—H41B | 109.5 |
C2—C3—H3D | 119.1 | H41A—C41—H41B | 109.5 |
C4—C3—H3D | 119.1 | N11—C41—H41C | 109.5 |
C3—C4—C9 | 120.1 (4) | H41A—C41—H41C | 109.5 |
C3—C4—C5 | 121.9 (5) | H41B—C41—H41C | 109.5 |
C9—C4—C5 | 118.0 (5) | O5—C42—N11 | 137.7 (15) |
C6—C5—C4 | 121.0 (5) | O5—C42—H42A | 111.2 |
C6—C5—H5A | 119.5 | N11—C42—H42A | 111.2 |
C4—C5—H5A | 119.5 | C41—N11—C42 | 119.4 (11) |
C5—C6—C7 | 121.3 (6) | C41—N11—C40 | 113.8 (10) |
C5—C6—H6C | 119.3 | C42—N11—C40 | 126.8 (9) |
C7—C6—H6C | 119.3 | N12—C43—H43A | 109.5 |
C6—C7—C8 | 120.7 (6) | N12—C43—H43B | 109.5 |
C6—C7—H7B | 119.6 | H43A—C43—H43B | 109.5 |
C8—C7—H7B | 119.6 | N12—C43—H43C | 109.5 |
C7—C8—C9 | 121.8 (5) | H43A—C43—H43C | 109.5 |
C7—C8—H8B | 119.1 | H43B—C43—H43C | 109.5 |
C9—C8—H8B | 119.1 | N12—C44—H44A | 109.5 |
C4—C9—C8 | 117.1 (4) | N12—C44—H44B | 109.5 |
C4—C9—C10 | 118.7 (4) | H44A—C44—H44B | 109.5 |
C8—C9—C10 | 124.2 (4) | N12—C44—H44C | 109.5 |
C1—C10—C9 | 119.1 (4) | H44A—C44—H44C | 109.5 |
C1—C10—C11 | 119.9 (4) | H44B—C44—H44C | 109.5 |
C9—C10—C11 | 120.9 (4) | O6—C45—N12 | 123.7 (11) |
N1—C11—C10 | 123.2 (4) | O6—C45—H45A | 118.1 |
N1—C11—H11A | 118.4 | N12—C45—H45A | 118.1 |
C10—C11—H11A | 118.4 | C45—N12—C44 | 120.4 (9) |
N2—C12—N3 | 124.7 (4) | C45—N12—C43 | 122.3 (9) |
N2—C12—S1 | 120.5 (3) | C44—N12—C43 | 117.2 (7) |
N3—C12—S1 | 114.8 (3) | N13—C46—H46A | 109.5 |
O2—C13—C22 | 122.2 (3) | N13—C46—H46B | 109.5 |
O2—C13—C14 | 117.3 (4) | H46A—C46—H46B | 109.5 |
C22—C13—C14 | 120.5 (4) | N13—C46—H46C | 109.5 |
C15—C14—C13 | 121.0 (4) | H46A—C46—H46C | 109.5 |
C15—C14—H14A | 119.5 | H46B—C46—H46C | 109.5 |
C13—C14—H14A | 119.5 | N13—C47—H47A | 109.5 |
C14—C15—C16 | 121.3 (4) | N13—C47—H47B | 109.5 |
C14—C15—H15A | 119.4 | H47A—C47—H47B | 109.5 |
C16—C15—H15A | 119.4 | N13—C47—H47C | 109.5 |
C15—C16—C17 | 121.5 (4) | H47A—C47—H47C | 109.5 |
C15—C16—C21 | 119.2 (4) | H47B—C47—H47C | 109.5 |
C17—C16—C21 | 119.3 (4) | O7—C48—N13 | 127.4 (7) |
C18—C17—C16 | 121.3 (4) | O7—C48—H48A | 116.3 |
C18—C17—H17A | 119.3 | N13—C48—H48A | 116.3 |
C16—C17—H17A | 119.3 | C48—N13—C47 | 118.8 (6) |
C17—C18—C19 | 120.1 (5) | C48—N13—C46 | 122.1 (7) |
C17—C18—H18A | 119.9 | C47—N13—C46 | 119.1 (7) |
C19—C18—H18A | 119.9 |
Symmetry code: (i) −x+1/2, −y+3/2, −z+1. |
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H3B···O4 | 0.86 | 1.98 | 2.835 (8) | 175 |
N6—H6B···O6i | 0.86 | 2.00 | 2.845 (7) | 166 |
N9—H9A···O5ii | 0.86 | 2.31 | 3.049 (8) | 145 |
N9—H9B···O7 | 0.86 | 2.02 | 2.870 (6) | 172 |
O1—H1B···N1 | 0.82 | 1.86 | 2.588 (5) | 147 |
O2—H2B···N4 | 0.82 | 1.85 | 2.583 (4) | 148 |
O3—H3C···N7 | 0.82 | 1.86 | 2.587 (5) | 147 |
Symmetry codes: (i) −x+1/2, −y+3/2, −z+1; (ii) −x+1/2, y−1/2, −z+1/2. |
Experimental details
Crystal data | |
Chemical formula | [Ag6(C12H10N3OS)6]·4C3H7NO |
Mr | 2405.34 |
Crystal system, space group | Monoclinic, C2/c |
Temperature (K) | 293 |
a, b, c (Å) | 24.604 (3), 18.877 (3), 24.816 (3) |
β (°) | 94.763 (3) |
V (Å3) | 11486 (3) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 1.17 |
Crystal size (mm) | 0.22 × 0.20 × 0.18 |
Data collection | |
Diffractometer | Bruker SMART CCD |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.238, 0.373 |
No. of measured, independent and observed [I > 2s(I)] reflections | 28454, 10056, 7829 |
Rint | 0.042 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.046, 0.145, 1.08 |
No. of reflections | 10056 |
No. of parameters | 667 |
No. of restraints | 63 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.92, −0.42 |
Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SHELXTL (Sheldrick, 2008).
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H3B···O4 | 0.86 | 1.98 | 2.835 (8) | 174.7 |
N6—H6B···O6i | 0.86 | 2.00 | 2.845 (7) | 165.6 |
N9—H9A···O5ii | 0.86 | 2.31 | 3.049 (8) | 144.5 |
N9—H9B···O7 | 0.86 | 2.02 | 2.870 (6) | 172.2 |
O1—H1B···N1 | 0.82 | 1.86 | 2.588 (5) | 147.0 |
O2—H2B···N4 | 0.82 | 1.85 | 2.583 (4) | 147.6 |
O3—H3C···N7 | 0.82 | 1.86 | 2.587 (5) | 146.7 |
Symmetry codes: (i) −x+1/2, −y+3/2, −z+1; (ii) −x+1/2, y−1/2, −z+1/2. |
Transition metal-chalcogen compounds, especially for d10 metal complexes, have attracted a great deal of attention for their interesting structures and excellent luminescent properties (Brito et al., 2011; Forward et al., 1995). Of which many coordination complexes with thiosemicarbazone Schiff base ligands have been reported (Ashfield et al., 2004; Castiñeiras & Pedrido, 2009; Li et al., 2010; Onodera et al., 2007; Pedrido et al., 2009). As a part of our studies on this class of compounds (Sun, 2011; Sun et al., 2012; Sun & Chai, 2012; Xu et al., 2011), we describe here the structure of the title compound.
The structure of the title compound is shown in Fig. 1. It contains an Ag6 hexanuclear cluster with the Ag···Ag distances varying from 2.93 Å to 3.40 Å (Fig. 2), which is shorter than the sum of van der Waals radii of two silver atoms (3.44 Å) (Han et al., 2004). In the cluster, each Ag(I) ion is surrounded by one nitrogen atom and two thiolate sulfur atoms from two deprotonated ligands L5. Each ligand coordinates to three Ag(I) ions using a bridged thiolate sulfur atom and a monodentate nitrogen atom, from which two Ag3S3 hexagonal rings are linked together to give the overall Ferris wheel structure.
There are intramolecular hydrogen bonds of O—H···N type. Besides this, solvent DMF molecules are linked to the hexanuclear cluster via O···H—N hydrogen bonds.
Packing of the title compound (Fig. 3) is facilitated through π–π stacking interactions between aromatic rings I, II [defined by the atoms C(1), C(2), C(3), C(4), C(9) and C(10) and the atoms C(13), C(14), C(15), C(16), C(21) and C(22), respectively] and the symmetry related ones (ring centroid distances: 3.78 Å and 3.70 Å, respectively).