research communications\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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COMMUNICATIONS
ISSN: 2056-9890

Crystal structure of bis­­[(acetato-κO)(imidazolidine-2-thione-κS)bis­­(tri­phenyl­phosphane-κP)silver(I)] di-μ-imidazol­idine-2-thione-κ4S:S-bis­­[(imidazol­id­ine-2-thione-κS)bis­­(tri­phenyl­phosphane-κP)silver(I)] di­acetate aceto­nitrile disolvate tetra­hydrate

CROSSMARK_Color_square_no_text.svg

aDepartment of Chemistry, Youngstown State University, 1 University Plaza, 44555 Youngstown, OH, USA, and bDepartment of Chemistry, Faculty of Science, Prince of Songkla University, Hat Yai, Songkhla 90112, Thailand
*Correspondence e-mail: yupa.t@psu.ac.th

Edited by M. Weil, Vienna University of Technology, Austria (Received 17 February 2016; accepted 22 February 2016; online 4 March 2016)

In the title compound, [Ag2(C3H6N2S)4(C18H15P)2](C2H3O2)2·[Ag(C2H3O2)(C3H6N2S)(C18H15P)2]2·2C2H3N·4H2O, the AgI ion in the mononuclear neutral complex exhibits a distorted tetra­hedral environment with coordination by two P atoms from tri­phenyl­phosphane (PPh3) ligands, one S atom of an imidazolidine-2-thione (etu) ligand and one O atom of an acetate anion. The binuclear cationic complex comprises two inversion-related [Ag(C3H6N2S)2(C18H15P)] units with AgI ions bridged by two S atoms from etu ligands forming a four-membered Ag–S–Ag–S ring. Each AgI ion is coordinated by a P atom of a PPh3 ligand, two S atoms of bridging etu ligands and the terminal S atom of an etu ligand in a distorted tetra­hedral environment. In the crystal, the mononuclear complex is linked to lattice water mol­ecules through O—H⋯O and N—H⋯O hydrogen bonds, forming a chain along [100]. In addition, the binuclear complex mol­ecules are connected to acetate anions and lattice water mol­ecules via O—H⋯O, N—H⋯O and O—H⋯S hydrogen bonds, also along [100].

1. Chemical context

Silver(I) complexes containing S- or P-donor ligands have received much attention because of their potential applications in biochemistry (Isab et al., 2010[Isab, A. A., Nawaz, S., Saleem, M., Altaf, M., Monim-ul-Mehboob, M., Ahmad, S. & Stoeckli-Evans, H. (2010). Polyhedron, 29, 1251-1256.]; Nawaz et al., 2011[Nawaz, S., Isab, A. A., Merz, K., Vasylyeva, V., Metzler-Nolte, N., Saleem, M. & Ahmad, S. (2011). Polyhedron, 30, 1502-1506.]) and their luminescent properties (Ferrari et al., 2007[Ferrari, M. B., Bisceglie, F., Cavalli, E., Pelosi, G., Tarasconi, P. & Verdolino, V. (2007). Inorg. Chim. Acta, 360, 3233-3240.]). The crystal structure of the title compound, [Ag(CH3COO)(C3H6N2S)(C18H15P)2]2·[Ag2(C3H6N2S)4(C18H15P)2](CH3COO)2·2CH3CN·4H2O, is presented herein.

[Scheme 1]

2. Structural commentary

The structures of the mol­ecular components of the title compound are shown in Fig. 1[link]. The crystal structure consists of a mononuclear neutral AgI complex, a discrete cationic binuclear AgI complex, acetate anions, aceto­nitrile solvent mol­ecules and water mol­ecules of crystallization. In the mononuclear complex, the AgI ion exhibits a distorted tetra­hedral environment, being coordinated by two P atoms of tri­phenyl­phosphane (PPh3) ligands, one terminal S atom of a imidazolidine-2-thione (or ethyl­ene­thio­urea; etu) ligand and an O atom of an acetate anion. The mol­ecule of the binuclear complex lies across a crystallographic inversion center which is at the center of the Ag2S2 core. The two AgI ions are bridged by two S atoms of etu ligands forming a four-membered Ag–S–Ag–S ring. Each AgI ion is in a distorted tetra­hedral coordination geometry formed by a P atom of a PPh3 ligand, the S atoms of two bridging etu ligands and a terminal S atom of an etu ligand.

[Figure 1]
Figure 1
The structures of the mol­ecular components with displacement ellipsoids drawn at the 50% probability level. H atoms are omitted for clarity. The symmetry operator for equivalent atoms of the discrete dimer is (−x, −y, −z + 1). Only the symmetry-unique mononuclear complex, acetate ion, aceto­nitrile solvent mol­ecule and solvent water mol­ecules are shown.

3. Supra­molecular features

In the crystal structure, O7—H7A⋯O6, O7—H7B⋯O6iv, N6—H6⋯O4 and N5—H5⋯O7iii hydrogen bonds (symmetry codes as in Table 1[link]) link the mononuclear complexes and water mol­ecules into chains along [100] (Fig. 2[link]). In addition, N1—H1⋯O1, N2—H2⋯O8i, N3—H3⋯O1, N4—H4⋯O2ii, O8—H8C⋯O2 and O8—H8D⋯S2iii hydrogen bonds connect the discrete binuclear complexes with acetate anions and water mol­ecules, forming another chain along [100] (Fig. 3[link]).

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N1—H1⋯O1 0.88 2.10 2.908 (3) 153
N2—H2⋯O8i 0.88 2.00 2.808 (3) 152
N3—H3⋯O1 0.88 1.94 2.780 (3) 160
N4—H4⋯O2ii 0.88 2.09 2.864 (3) 146
N5—H5⋯O7iii 0.88 1.96 2.767 (3) 152
N6—H6⋯O4 0.88 1.91 2.780 (3) 172
O7—H7A⋯O6 0.85 (1) 1.88 (1) 2.716 (3) 169 (4)
O7—H7B⋯O6iv 0.84 (1) 2.00 (2) 2.782 (3) 154 (3)
O8—H8C⋯O2 0.84 (1) 1.88 (1) 2.709 (3) 167 (3)
O8—H8D⋯S2iii 0.84 (1) 2.56 (2) 3.357 (2) 159 (3)
Symmetry codes: (i) -x+1, -y, -z+1; (ii) x-1, y, z; (iii) x+1, y, z; (iv) -x, -y+1, -z.
[Figure 2]
Figure 2
Part of the crystal structure with O—H⋯O and N—H⋯O hydrogen bonds shown as dashed lines (symmetry codes as in Table 1[link]).
[Figure 3]
Figure 3
Part of the crystal structure with O—H⋯O, N—H⋯O and O—H⋯S hydrogen bonds shown as dashed lines (symmetry codes as in Table 1[link]).

4. Synthesis and crystallization

Tri­phenyl­phosphane (0.31 g, 1.18 mmol) was dissolved in 30 cm3 of aceto­nitrile at 335 K. Ag(OAc) (0.10 g, 0.60 mmol) was added and the mixture was stirred for 3 h. Ethyl­ene­thio­urea (0.06 g, 0.59 mmol) was added and the new reaction mixture was heated under reflux for 5 h. The resulting clear solution was filtered off and left to evaporate at room temperature. Crystals suitable for X-ray diffraction, which were deposited upon standing for a week, were filtered off and dried under reduced pressure.

5. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2[link]. All C- and N-bound H atoms were constrained with a riding model: 0.95 Å (aryl H) and Uiso(H) = 1.2Ueq(C); 0.99 Å (CH2) and Uiso(H) = 1.2Ueq(C); 0.98 Å (CH3) and Uiso(H) = 1.5Ueq(C); 0.88 Å (NH) and Uiso(H) = 1.2Ueq(N). Water hydrogen atoms were located from a difference Fourier map and were refined with an O—H distance restraint of 0.84 (2) Å and Uiso(H) = 1.2Ueq(O).

Table 2
Experimental details

Crystal data
Chemical formula [Ag2(C3H6N2S)4(C18H15P)2](C2H3O2)2·[Ag(C2H3O2)(C3H6N2S)(C18H15P)2]2·2C2H3N·4H2O
Mr 3008.39
Crystal system, space group Triclinic, P[\overline{1}]
Temperature (K) 100
a, b, c (Å) 9.5867 (4), 16.3018 (7), 22.8548 (10)
α, β, γ (°) 104.179 (2), 94.449 (2), 91.992 (2)
V3) 3447.2 (3)
Z 1
Radiation type Mo Kα
μ (mm−1) 0.78
Crystal size (mm) 0.16 × 0.15 × 0.13
 
Data collection
Diffractometer Bruker AXS D8 Quest CMOS
Absorption correction Multi-scan (SADABS; Bruker, 2014[Bruker (2014). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.])
Tmin, Tmax 0.882, 0.903
No. of measured, independent and observed [I > 2σ(I)] reflections 71762, 20957, 18898
Rint 0.026
(sin θ/λ)max−1) 0.716
 
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.042, 0.088, 1.26
No. of reflections 20957
No. of parameters 826
No. of restraints 6
H-atom treatment H atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3) 1.05, −0.97
Computer programs: APEX2 and SAINT (Bruker, 2014[Bruker (2014). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]), SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]), SHELXL2014 (Sheldrick, 2015[Sheldrick, G. M. (2015). Acta Cryst. C71, 3-8.]), SHELXLE (Hübschle et al., 2011[Hübschle, C. B., Sheldrick, G. M. & Dittrich, B. (2011). J. Appl. Cryst. 44, 1281-1284.]), Mercury (Macrae et al., 2008[Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.]) and publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).

Supporting information


Computing details top

Data collection: APEX2 (Bruker, 2014); cell refinement: SAINT (Bruker, 2014); data reduction: SAINT (Bruker, 2014); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015) and SHELXLE (Hübschle et al., 2011); molecular graphics: Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015) and publCIF (Westrip, 2010).

Bis[(acetato-κO)(imidazolidine-2-thione-κS)bis(triphenylphosphane-κP)silver(I)] di-µ-imidazolidine-2-thione-κ4S:S-bis[(imidazolidine-2-thione-κS)bis(triphenylphosphane-κP)silver(I)] diacetate acetonitrile disolvate tetrahydrate top
Crystal data top
[Ag2(C3H6N2S)4(C18H15P)2](C2H3O2)2·[Ag(C2H3O2)(C3H6N2S)(C18H15P)2]2·2C2H3N·4H2OZ = 1
Mr = 3008.39F(000) = 1548
Triclinic, P1Dx = 1.449 Mg m3
a = 9.5867 (4) ÅMo Kα radiation, λ = 0.71073 Å
b = 16.3018 (7) ÅCell parameters from 9707 reflections
c = 22.8548 (10) Åθ = 2.4–30.6°
α = 104.179 (2)°µ = 0.78 mm1
β = 94.449 (2)°T = 100 K
γ = 91.992 (2)°Block, colourless
V = 3447.2 (3) Å30.16 × 0.15 × 0.13 mm
Data collection top
Bruker AXS D8 Quest CMOS
diffractometer
20957 independent reflections
Radiation source: I-mu-S microsource X-ray tube18898 reflections with I > 2σ(I)
Laterally graded multilayer (Goebel) mirror monochromatorRint = 0.026
ω and φ scansθmax = 30.6°, θmin = 2.3°
Absorption correction: multi-scan
(SADABS; Bruker, 2014)
h = 1313
Tmin = 0.882, Tmax = 0.903k = 2323
71762 measured reflectionsl = 3232
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)] = 0.042Hydrogen site location: mixed
wR(F2) = 0.088H atoms treated by a mixture of independent and constrained refinement
S = 1.26 w = 1/[σ2(Fo2) + (0.0001P)2 + 7.6382P]
where P = (Fo2 + 2Fc2)/3
20957 reflections(Δ/σ)max = 0.002
826 parametersΔρmax = 1.05 e Å3
6 restraintsΔρmin = 0.97 e Å3
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Ag10.35807 (2)0.29775 (2)0.13070 (2)0.01524 (4)
Ag20.00978 (2)0.12147 (2)0.53974 (2)0.01655 (4)
S10.19225 (6)0.01029 (4)0.50712 (3)0.01504 (10)
S20.08966 (6)0.20987 (4)0.47189 (3)0.01634 (11)
S30.51845 (7)0.36676 (4)0.07081 (3)0.02254 (13)
P10.05184 (6)0.15244 (4)0.64996 (3)0.01168 (10)
P20.41455 (6)0.32402 (4)0.24144 (3)0.01230 (10)
P30.21550 (6)0.17470 (4)0.07067 (3)0.01362 (11)
N10.3296 (2)0.11367 (13)0.45141 (10)0.0187 (4)
H10.29040.15910.47110.022*
N20.3752 (2)0.01974 (14)0.42198 (10)0.0212 (4)
H20.36630.07480.41780.025*
N30.0389 (2)0.34962 (14)0.54878 (11)0.0213 (4)
H30.12020.32630.54960.026*
N40.1850 (2)0.36111 (14)0.52721 (11)0.0237 (5)
H40.26930.34910.50810.028*
N50.6169 (2)0.53077 (15)0.10791 (12)0.0261 (5)
H50.69870.52040.09350.031*
N60.4141 (2)0.50600 (14)0.13962 (11)0.0218 (4)
H60.33360.47950.14150.026*
C10.3025 (2)0.03624 (14)0.45799 (10)0.0140 (4)
C20.4331 (3)0.11450 (16)0.40730 (11)0.0200 (5)
H2A0.51590.15270.42580.024*
H2B0.39170.13220.37160.024*
C30.4719 (3)0.02121 (17)0.39010 (12)0.0213 (5)
H3A0.45730.00290.34580.026*
H3B0.57060.01540.40410.026*
C40.0783 (2)0.31014 (15)0.51795 (11)0.0161 (4)
C50.0153 (3)0.43661 (19)0.58100 (17)0.0362 (8)
H5A0.06160.47820.56260.043*
H5B0.04990.44800.62430.043*
C60.1436 (3)0.43931 (17)0.57316 (14)0.0265 (6)
H6A0.18550.44000.61150.032*
H6B0.17170.48960.55910.032*
C70.5159 (3)0.47123 (16)0.10718 (12)0.0190 (5)
N70.2420 (3)0.76608 (18)0.14911 (13)0.0381 (6)
C80.5723 (3)0.61517 (18)0.13593 (16)0.0312 (6)
H8A0.53810.64470.10500.037*
H8B0.64920.65040.16290.037*
C90.4533 (3)0.59427 (17)0.17195 (13)0.0246 (5)
H9A0.48640.59910.21480.030*
H9B0.37430.63130.17010.030*
C110.0123 (2)0.24930 (14)0.69579 (10)0.0142 (4)
C120.0554 (3)0.29479 (15)0.75139 (11)0.0180 (4)
H120.14000.27560.76660.022*
C130.0003 (3)0.36812 (17)0.78470 (12)0.0232 (5)
H130.04600.39850.82240.028*
C140.1231 (3)0.39624 (17)0.76243 (14)0.0264 (6)
H140.16060.44640.78470.032*
C150.1915 (3)0.35125 (17)0.70770 (14)0.0261 (6)
H150.27670.37030.69300.031*
C160.1362 (3)0.27823 (16)0.67406 (12)0.0207 (5)
H160.18310.24820.63630.025*
C210.2363 (2)0.15765 (14)0.67815 (10)0.0136 (4)
C220.2822 (3)0.13182 (16)0.72991 (11)0.0175 (4)
H220.21810.10400.74940.021*
C230.4223 (3)0.14682 (17)0.75313 (12)0.0222 (5)
H230.45280.13040.78890.027*
C240.5172 (3)0.18550 (17)0.72422 (12)0.0229 (5)
H240.61220.19650.74050.027*
C250.4728 (3)0.20824 (17)0.67126 (12)0.0212 (5)
H250.53840.23330.65080.025*
C260.3329 (2)0.19467 (15)0.64797 (11)0.0170 (4)
H260.30320.21040.61180.020*
C310.0272 (2)0.06841 (14)0.67890 (10)0.0131 (4)
C300.3989 (2)0.33050 (16)0.51551 (11)0.0175 (4)
C320.1146 (2)0.08315 (16)0.72606 (11)0.0175 (4)
H320.13370.13950.74570.021*
C330.1739 (3)0.01499 (18)0.74438 (12)0.0225 (5)
H330.23360.02510.77640.027*
C340.1459 (3)0.06732 (18)0.71596 (12)0.0235 (5)
H340.18620.11340.72870.028*
C350.0590 (3)0.08267 (16)0.66897 (12)0.0218 (5)
H350.03970.13920.64970.026*
C360.0004 (3)0.01517 (15)0.65027 (11)0.0172 (4)
H360.05820.02580.61790.021*
C410.5210 (2)0.42249 (15)0.27211 (10)0.0145 (4)
C400.3705 (3)0.41859 (18)0.50781 (15)0.0291 (6)
H40A0.40020.42410.46880.044*
H40B0.42290.46110.54070.044*
H40C0.27000.42730.50890.044*
C420.6444 (3)0.43300 (16)0.24514 (12)0.0190 (5)
H420.67210.38870.21350.023*
C430.7267 (3)0.50853 (17)0.26481 (13)0.0232 (5)
H430.81170.51490.24720.028*
C440.6852 (3)0.57443 (17)0.30988 (13)0.0251 (5)
H440.74120.62590.32290.030*
C450.5623 (3)0.56490 (16)0.33580 (12)0.0237 (5)
H450.53300.61030.36620.028*
C460.4808 (3)0.48901 (16)0.31759 (11)0.0195 (5)
H460.39730.48260.33630.023*
C510.5182 (2)0.24246 (15)0.26282 (10)0.0141 (4)
C500.0661 (2)0.41834 (15)0.11199 (11)0.0161 (4)
C520.4795 (3)0.15807 (15)0.23323 (11)0.0171 (4)
H520.40370.14580.20250.021*
C530.5502 (3)0.09187 (17)0.24805 (12)0.0217 (5)
H530.52260.03480.22770.026*
C540.6620 (3)0.10971 (17)0.29293 (12)0.0218 (5)
H540.71090.06480.30320.026*
C550.7016 (3)0.19306 (18)0.32251 (12)0.0227 (5)
H550.77780.20500.35300.027*
C560.6304 (3)0.25949 (17)0.30779 (11)0.0195 (5)
H560.65810.31640.32830.023*
C610.2704 (2)0.33088 (14)0.29028 (10)0.0138 (4)
C600.0750 (3)0.39096 (18)0.12854 (13)0.0230 (5)
H60A0.12420.35050.09350.034*
H60B0.13080.44060.14050.034*
H60C0.06140.36410.16240.034*
C620.2795 (3)0.30307 (16)0.34366 (11)0.0178 (4)
H620.36430.28170.35660.021*
C630.1651 (3)0.30661 (16)0.37794 (11)0.0193 (5)
H630.17170.28730.41400.023*
C640.0407 (3)0.33849 (16)0.35943 (11)0.0199 (5)
H640.03760.34060.38270.024*
C650.0315 (3)0.36712 (18)0.30680 (12)0.0223 (5)
H650.05280.38970.29450.027*
C660.1455 (3)0.36293 (17)0.27185 (11)0.0188 (5)
H660.13820.38180.23560.023*
C710.2823 (2)0.07331 (15)0.07579 (10)0.0159 (4)
C720.4256 (3)0.06359 (19)0.07134 (13)0.0255 (5)
H720.48300.10800.06400.031*
C730.4845 (3)0.0111 (2)0.07757 (15)0.0324 (6)
H730.58180.01760.07400.039*
C740.4020 (3)0.07579 (19)0.08886 (13)0.0299 (6)
H740.44280.12630.09370.036*
C750.2597 (3)0.06688 (18)0.09311 (13)0.0283 (6)
H750.20270.11150.10040.034*
C760.2004 (3)0.00746 (17)0.08673 (12)0.0224 (5)
H760.10280.01330.08990.027*
C810.0388 (2)0.17016 (15)0.09452 (11)0.0161 (4)
C820.0243 (3)0.17916 (18)0.15620 (12)0.0234 (5)
H820.10540.18640.18400.028*
C830.1077 (3)0.1775 (2)0.17707 (13)0.0307 (6)
H830.11670.18280.21890.037*
C840.2265 (3)0.1683 (2)0.13677 (14)0.0336 (7)
H840.31690.16780.15100.040*
C850.2131 (3)0.1599 (2)0.07591 (14)0.0320 (7)
H850.29470.15370.04850.038*
C860.0806 (3)0.16040 (18)0.05428 (12)0.0238 (5)
H860.07230.15410.01230.029*
C910.1855 (2)0.16749 (15)0.00985 (10)0.0146 (4)
C920.1600 (2)0.09072 (16)0.05353 (11)0.0168 (4)
H920.16730.03870.04210.020*
C930.1239 (3)0.09019 (18)0.11384 (11)0.0218 (5)
H930.10830.03790.14360.026*
C940.1108 (3)0.16631 (18)0.13052 (11)0.0231 (5)
H940.08260.16590.17140.028*
C950.1388 (3)0.24292 (17)0.08762 (12)0.0224 (5)
H950.13140.29480.09930.027*
C960.1776 (3)0.24370 (16)0.02761 (11)0.0197 (5)
H960.19890.29610.00150.024*
O10.29782 (18)0.28441 (11)0.52369 (8)0.0178 (3)
O20.52335 (19)0.30909 (13)0.51366 (10)0.0287 (4)
O40.17335 (17)0.40868 (11)0.14454 (8)0.0181 (3)
O60.0685 (2)0.45087 (16)0.06758 (10)0.0339 (5)
O70.1503 (2)0.54379 (13)0.04566 (9)0.0258 (4)
H7A0.088 (3)0.5092 (18)0.0496 (16)0.031*
H7B0.153 (4)0.543 (2)0.0086 (6)0.031*
O80.6376 (2)0.17707 (13)0.54856 (9)0.0254 (4)
H8C0.591 (3)0.2133 (17)0.5363 (15)0.030*
H8D0.699 (3)0.172 (2)0.5241 (12)0.030*
C100.2216 (3)0.71407 (19)0.10551 (14)0.0289 (6)
C200.1970 (4)0.6458 (2)0.05039 (15)0.0396 (8)
H20A0.10730.65250.02880.059*
H20B0.19430.59110.06100.059*
H20C0.27280.64800.02430.059*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ag10.01534 (8)0.01640 (8)0.01295 (8)0.00237 (6)0.00027 (6)0.00259 (6)
Ag20.01955 (9)0.01800 (9)0.01197 (8)0.00333 (6)0.00106 (6)0.00327 (6)
S10.0137 (2)0.0150 (3)0.0165 (3)0.00022 (19)0.00441 (19)0.0032 (2)
S20.0175 (3)0.0181 (3)0.0138 (2)0.0006 (2)0.0003 (2)0.0055 (2)
S30.0233 (3)0.0220 (3)0.0224 (3)0.0022 (2)0.0107 (2)0.0033 (2)
P10.0120 (2)0.0129 (3)0.0099 (2)0.00055 (19)0.00173 (19)0.00199 (19)
P20.0120 (2)0.0137 (3)0.0110 (2)0.0001 (2)0.00039 (19)0.0031 (2)
P30.0127 (3)0.0154 (3)0.0118 (2)0.0029 (2)0.0012 (2)0.0020 (2)
N10.0195 (10)0.0164 (10)0.0210 (10)0.0005 (8)0.0085 (8)0.0038 (8)
N20.0245 (11)0.0150 (10)0.0255 (11)0.0020 (8)0.0122 (9)0.0045 (8)
N30.0115 (9)0.0175 (10)0.0316 (12)0.0023 (7)0.0015 (8)0.0007 (9)
N40.0117 (9)0.0199 (11)0.0378 (13)0.0011 (8)0.0014 (9)0.0051 (9)
N50.0183 (10)0.0225 (11)0.0388 (14)0.0011 (8)0.0103 (9)0.0081 (10)
N60.0159 (10)0.0192 (10)0.0301 (12)0.0022 (8)0.0063 (8)0.0046 (9)
C10.0126 (10)0.0140 (10)0.0142 (10)0.0011 (8)0.0010 (8)0.0016 (8)
C20.0204 (12)0.0207 (12)0.0191 (11)0.0028 (9)0.0065 (9)0.0042 (9)
C30.0200 (12)0.0243 (13)0.0225 (12)0.0031 (9)0.0106 (9)0.0083 (10)
C40.0135 (10)0.0167 (11)0.0200 (11)0.0002 (8)0.0024 (8)0.0082 (9)
C50.0166 (12)0.0214 (14)0.060 (2)0.0029 (10)0.0037 (13)0.0095 (13)
C60.0192 (12)0.0206 (13)0.0376 (15)0.0052 (10)0.0014 (11)0.0032 (11)
C70.0157 (11)0.0209 (12)0.0225 (12)0.0014 (9)0.0033 (9)0.0092 (9)
N70.0502 (17)0.0299 (14)0.0330 (14)0.0094 (12)0.0059 (12)0.0074 (11)
C80.0243 (14)0.0217 (13)0.0487 (18)0.0023 (11)0.0091 (12)0.0094 (12)
C90.0216 (12)0.0203 (12)0.0329 (14)0.0025 (10)0.0040 (10)0.0076 (11)
C110.0142 (10)0.0136 (10)0.0147 (10)0.0002 (8)0.0034 (8)0.0031 (8)
C120.0200 (11)0.0167 (11)0.0165 (11)0.0005 (9)0.0032 (9)0.0023 (9)
C130.0264 (13)0.0185 (12)0.0215 (12)0.0042 (10)0.0077 (10)0.0021 (9)
C140.0273 (13)0.0164 (12)0.0351 (15)0.0033 (10)0.0168 (11)0.0008 (10)
C150.0201 (12)0.0205 (13)0.0388 (16)0.0064 (10)0.0070 (11)0.0072 (11)
C160.0172 (11)0.0196 (12)0.0232 (12)0.0030 (9)0.0013 (9)0.0014 (9)
C210.0139 (10)0.0128 (10)0.0132 (10)0.0005 (8)0.0019 (8)0.0013 (8)
C220.0174 (11)0.0190 (11)0.0166 (11)0.0026 (9)0.0016 (8)0.0052 (9)
C230.0210 (12)0.0243 (13)0.0198 (12)0.0059 (10)0.0027 (9)0.0034 (10)
C240.0148 (11)0.0221 (12)0.0276 (13)0.0020 (9)0.0006 (9)0.0010 (10)
C250.0155 (11)0.0217 (12)0.0246 (12)0.0030 (9)0.0070 (9)0.0011 (10)
C260.0160 (11)0.0173 (11)0.0173 (11)0.0002 (8)0.0039 (8)0.0030 (9)
C310.0117 (9)0.0152 (10)0.0119 (9)0.0014 (8)0.0009 (7)0.0035 (8)
C300.0147 (10)0.0178 (11)0.0203 (11)0.0007 (8)0.0004 (8)0.0059 (9)
C320.0165 (11)0.0212 (12)0.0136 (10)0.0009 (9)0.0026 (8)0.0018 (9)
C330.0209 (12)0.0299 (14)0.0177 (11)0.0035 (10)0.0045 (9)0.0074 (10)
C340.0216 (12)0.0262 (13)0.0251 (13)0.0058 (10)0.0003 (10)0.0127 (10)
C350.0236 (12)0.0172 (11)0.0256 (13)0.0007 (9)0.0025 (10)0.0074 (10)
C360.0187 (11)0.0166 (11)0.0165 (11)0.0002 (9)0.0040 (8)0.0037 (9)
C410.0162 (10)0.0154 (10)0.0121 (10)0.0008 (8)0.0012 (8)0.0049 (8)
C400.0271 (14)0.0197 (13)0.0434 (17)0.0021 (10)0.0022 (12)0.0143 (12)
C420.0168 (11)0.0184 (11)0.0212 (12)0.0023 (9)0.0027 (9)0.0043 (9)
C430.0172 (11)0.0233 (13)0.0299 (14)0.0054 (9)0.0009 (10)0.0093 (10)
C440.0254 (13)0.0175 (12)0.0308 (14)0.0034 (10)0.0065 (11)0.0064 (10)
C450.0304 (14)0.0160 (11)0.0213 (12)0.0001 (10)0.0025 (10)0.0004 (9)
C460.0209 (12)0.0199 (12)0.0167 (11)0.0019 (9)0.0022 (9)0.0023 (9)
C510.0137 (10)0.0167 (10)0.0130 (10)0.0006 (8)0.0032 (8)0.0054 (8)
C500.0168 (11)0.0163 (11)0.0160 (10)0.0029 (8)0.0036 (8)0.0047 (8)
C520.0169 (11)0.0180 (11)0.0168 (11)0.0002 (8)0.0032 (8)0.0049 (9)
C530.0241 (12)0.0178 (12)0.0237 (12)0.0023 (9)0.0053 (10)0.0051 (9)
C540.0200 (12)0.0257 (13)0.0245 (12)0.0067 (10)0.0070 (9)0.0133 (10)
C550.0176 (11)0.0305 (14)0.0226 (12)0.0019 (10)0.0022 (9)0.0124 (10)
C560.0170 (11)0.0210 (12)0.0199 (11)0.0007 (9)0.0020 (9)0.0054 (9)
C610.0127 (10)0.0148 (10)0.0131 (10)0.0015 (8)0.0015 (8)0.0022 (8)
C600.0142 (11)0.0269 (13)0.0304 (14)0.0000 (9)0.0018 (9)0.0122 (11)
C620.0189 (11)0.0210 (12)0.0145 (10)0.0020 (9)0.0016 (8)0.0062 (9)
C630.0240 (12)0.0194 (11)0.0159 (11)0.0015 (9)0.0045 (9)0.0069 (9)
C640.0177 (11)0.0216 (12)0.0200 (11)0.0020 (9)0.0070 (9)0.0031 (9)
C650.0165 (11)0.0315 (14)0.0214 (12)0.0062 (10)0.0049 (9)0.0093 (10)
C660.0158 (11)0.0267 (13)0.0163 (11)0.0034 (9)0.0031 (8)0.0096 (9)
C710.0153 (10)0.0197 (11)0.0120 (10)0.0001 (8)0.0003 (8)0.0031 (8)
C720.0166 (12)0.0298 (14)0.0309 (14)0.0018 (10)0.0053 (10)0.0082 (11)
C730.0232 (14)0.0375 (17)0.0369 (16)0.0122 (12)0.0029 (12)0.0085 (13)
C740.0380 (16)0.0276 (14)0.0237 (13)0.0110 (12)0.0027 (11)0.0059 (11)
C750.0359 (15)0.0226 (13)0.0267 (14)0.0001 (11)0.0005 (11)0.0080 (11)
C760.0211 (12)0.0211 (12)0.0245 (13)0.0007 (9)0.0012 (10)0.0050 (10)
C810.0155 (10)0.0158 (11)0.0163 (10)0.0026 (8)0.0044 (8)0.0024 (8)
C820.0228 (12)0.0295 (14)0.0182 (12)0.0027 (10)0.0054 (9)0.0058 (10)
C830.0321 (15)0.0379 (16)0.0224 (13)0.0029 (12)0.0153 (11)0.0046 (12)
C840.0222 (13)0.0395 (17)0.0350 (16)0.0066 (12)0.0158 (12)0.0014 (13)
C850.0150 (12)0.0482 (19)0.0289 (14)0.0052 (12)0.0057 (10)0.0020 (13)
C860.0155 (11)0.0340 (15)0.0197 (12)0.0047 (10)0.0042 (9)0.0024 (10)
C910.0106 (9)0.0182 (11)0.0142 (10)0.0019 (8)0.0015 (8)0.0030 (8)
C920.0158 (10)0.0185 (11)0.0156 (10)0.0012 (8)0.0038 (8)0.0025 (8)
C930.0214 (12)0.0270 (13)0.0145 (11)0.0012 (10)0.0035 (9)0.0001 (9)
C940.0211 (12)0.0337 (14)0.0141 (11)0.0007 (10)0.0019 (9)0.0057 (10)
C950.0247 (13)0.0245 (13)0.0197 (12)0.0006 (10)0.0022 (9)0.0088 (10)
C960.0209 (12)0.0191 (12)0.0188 (11)0.0010 (9)0.0028 (9)0.0039 (9)
O10.0140 (8)0.0153 (8)0.0240 (9)0.0006 (6)0.0032 (6)0.0045 (7)
O20.0113 (8)0.0303 (11)0.0466 (13)0.0004 (7)0.0039 (8)0.0133 (9)
O40.0128 (8)0.0234 (9)0.0193 (8)0.0024 (6)0.0015 (6)0.0075 (7)
O60.0216 (10)0.0611 (15)0.0306 (11)0.0087 (10)0.0066 (8)0.0312 (11)
O70.0241 (10)0.0294 (10)0.0280 (10)0.0050 (8)0.0099 (8)0.0124 (8)
O80.0221 (9)0.0290 (10)0.0298 (10)0.0070 (8)0.0111 (8)0.0126 (8)
C100.0291 (14)0.0287 (15)0.0308 (15)0.0032 (11)0.0002 (11)0.0117 (12)
C200.0369 (17)0.0422 (19)0.0332 (17)0.0070 (14)0.0029 (13)0.0016 (14)
Geometric parameters (Å, º) top
Ag1—P32.4381 (6)C34—H340.9500
Ag1—P22.4744 (6)C35—C361.391 (3)
Ag1—S32.5424 (7)C35—H350.9500
Ag1—O42.5564 (17)C36—H360.9500
Ag2—P12.4431 (6)C41—C461.394 (3)
Ag2—S22.5200 (6)C41—C421.400 (3)
Ag2—S12.5810 (6)C40—H40A0.9800
Ag2—S1i2.7883 (6)C40—H40B0.9800
S1—C11.715 (2)C40—H40C0.9800
S1—Ag2i2.7883 (6)C42—C431.395 (3)
S2—C41.708 (3)C42—H420.9500
S3—C71.704 (3)C43—C441.387 (4)
P1—C111.824 (2)C43—H430.9500
P1—C211.826 (2)C44—C451.380 (4)
P1—C311.827 (2)C44—H440.9500
P2—C511.824 (2)C45—C461.395 (4)
P2—C411.826 (2)C45—H450.9500
P2—C611.832 (2)C46—H460.9500
P3—C911.814 (2)C51—C521.399 (3)
P3—C711.820 (3)C51—C561.399 (3)
P3—C811.824 (2)C50—O61.256 (3)
N1—C11.327 (3)C50—O41.259 (3)
N1—C21.470 (3)C50—C601.514 (3)
N1—H10.8800C52—C531.390 (3)
N2—C11.327 (3)C52—H520.9500
N2—C31.462 (3)C53—C541.395 (4)
N2—H20.8800C53—H530.9500
N3—C41.333 (3)C54—C551.386 (4)
N3—C51.463 (3)C54—H540.9500
N3—H30.8800C55—C561.395 (4)
N4—C41.337 (3)C55—H550.9500
N4—C61.460 (4)C56—H560.9500
N4—H40.8800C61—C661.399 (3)
N5—C71.343 (3)C61—C621.399 (3)
N5—C81.462 (4)C60—H60A0.9800
N5—H50.8800C60—H60B0.9800
N6—C71.330 (3)C60—H60C0.9800
N6—C91.468 (3)C62—C631.392 (3)
N6—H60.8800C62—H620.9500
C2—C31.541 (4)C63—C641.394 (4)
C2—H2A0.9900C63—H630.9500
C2—H2B0.9900C64—C651.391 (4)
C3—H3A0.9900C64—H640.9500
C3—H3B0.9900C65—C661.397 (3)
C5—C61.523 (4)C65—H650.9500
C5—H5A0.9900C66—H660.9500
C5—H5B0.9900C71—C761.391 (3)
C6—H6A0.9900C71—C721.397 (3)
C6—H6B0.9900C72—C731.394 (4)
N7—C101.138 (4)C72—H720.9500
C8—C91.533 (4)C73—C741.382 (5)
C8—H8A0.9900C73—H730.9500
C8—H8B0.9900C74—C751.385 (4)
C9—H9A0.9900C74—H740.9500
C9—H9B0.9900C75—C761.391 (4)
C11—C161.394 (3)C75—H750.9500
C11—C121.401 (3)C76—H760.9500
C12—C131.398 (3)C81—C861.391 (3)
C12—H120.9500C81—C821.400 (3)
C13—C141.384 (4)C82—C831.388 (4)
C13—H130.9500C82—H820.9500
C14—C151.386 (4)C83—C841.387 (5)
C14—H140.9500C83—H830.9500
C15—C161.396 (4)C84—C851.380 (4)
C15—H150.9500C84—H840.9500
C16—H160.9500C85—C861.398 (4)
C21—C221.395 (3)C85—H850.9500
C21—C261.400 (3)C86—H860.9500
C22—C231.396 (3)C91—C921.397 (3)
C22—H220.9500C91—C961.401 (3)
C23—C241.385 (4)C92—C931.393 (3)
C23—H230.9500C92—H920.9500
C24—C251.391 (4)C93—C941.391 (4)
C24—H240.9500C93—H930.9500
C25—C261.394 (3)C94—C951.389 (4)
C25—H250.9500C94—H940.9500
C26—H260.9500C95—C961.390 (3)
C31—C321.396 (3)C95—H950.9500
C31—C361.402 (3)C96—H960.9500
C30—O21.255 (3)O7—H7A0.848 (10)
C30—O11.259 (3)O7—H7B0.844 (10)
C30—C401.520 (4)O8—H8C0.842 (10)
C32—C331.398 (4)O8—H8D0.837 (10)
C32—H320.9500C10—C201.459 (4)
C33—C341.385 (4)C20—H20A0.9800
C33—H330.9500C20—H20B0.9800
C34—C351.390 (4)C20—H20C0.9800
P3—Ag1—P2123.16 (2)C34—C33—H33119.9
P3—Ag1—S3114.75 (2)C32—C33—H33119.9
P2—Ag1—S3118.40 (2)C33—C34—C35120.2 (2)
P3—Ag1—O499.89 (4)C33—C34—H34119.9
P2—Ag1—O491.92 (4)C35—C34—H34119.9
S3—Ag1—O497.56 (4)C34—C35—C36119.9 (2)
P1—Ag2—S2130.88 (2)C34—C35—H35120.1
P1—Ag2—S1100.98 (2)C36—C35—H35120.1
S2—Ag2—S1122.99 (2)C35—C36—C31120.4 (2)
P1—Ag2—S1i112.706 (19)C35—C36—H36119.8
S2—Ag2—S1i92.547 (19)C31—C36—H36119.8
S1—Ag2—S1i86.195 (19)C46—C41—C42119.1 (2)
C1—S1—Ag2113.31 (8)C46—C41—P2123.41 (19)
C1—S1—Ag2i117.47 (8)C42—C41—P2117.39 (18)
Ag2—S1—Ag2i93.806 (19)C30—C40—H40A109.5
C4—S2—Ag2103.55 (8)C30—C40—H40B109.5
C7—S3—Ag1101.86 (9)H40A—C40—H40B109.5
C11—P1—C21103.14 (10)C30—C40—H40C109.5
C11—P1—C31103.96 (10)H40A—C40—H40C109.5
C21—P1—C31103.77 (10)H40B—C40—H40C109.5
C11—P1—Ag2119.00 (8)C43—C42—C41119.9 (2)
C21—P1—Ag2114.48 (8)C43—C42—H42120.0
C31—P1—Ag2110.90 (7)C41—C42—H42120.0
C51—P2—C41104.65 (11)C44—C43—C42120.5 (2)
C51—P2—C61102.56 (10)C44—C43—H43119.8
C41—P2—C61104.66 (11)C42—C43—H43119.8
C51—P2—Ag1113.13 (8)C45—C44—C43119.7 (2)
C41—P2—Ag1111.70 (7)C45—C44—H44120.1
C61—P2—Ag1118.76 (7)C43—C44—H44120.1
C91—P3—C71105.22 (11)C44—C45—C46120.4 (2)
C91—P3—C81103.32 (11)C44—C45—H45119.8
C71—P3—C81103.63 (11)C46—C45—H45119.8
C91—P3—Ag1116.27 (8)C41—C46—C45120.4 (2)
C71—P3—Ag1114.34 (8)C41—C46—H46119.8
C81—P3—Ag1112.68 (8)C45—C46—H46119.8
C1—N1—C2111.9 (2)C52—C51—C56118.8 (2)
C1—N1—H1124.0C52—C51—P2117.31 (17)
C2—N1—H1124.0C56—C51—P2123.89 (19)
C1—N2—C3111.8 (2)O6—C50—O4124.2 (2)
C1—N2—H2124.1O6—C50—C60118.0 (2)
C3—N2—H2124.1O4—C50—C60117.7 (2)
C4—N3—C5111.5 (2)C53—C52—C51121.0 (2)
C4—N3—H3124.3C53—C52—H52119.5
C5—N3—H3124.3C51—C52—H52119.5
C4—N4—C6111.2 (2)C52—C53—C54119.6 (2)
C4—N4—H4124.4C52—C53—H53120.2
C6—N4—H4124.4C54—C53—H53120.2
C7—N5—C8110.7 (2)C55—C54—C53120.0 (2)
C7—N5—H5124.6C55—C54—H54120.0
C8—N5—H5124.6C53—C54—H54120.0
C7—N6—C9111.3 (2)C54—C55—C56120.5 (2)
C7—N6—H6124.4C54—C55—H55119.8
C9—N6—H6124.4C56—C55—H55119.8
N1—C1—N2110.7 (2)C55—C56—C51120.2 (2)
N1—C1—S1125.64 (18)C55—C56—H56119.9
N2—C1—S1123.62 (18)C51—C56—H56119.9
N1—C2—C3102.27 (19)C66—C61—C62119.4 (2)
N1—C2—H2A111.3C66—C61—P2117.91 (17)
C3—C2—H2A111.3C62—C61—P2122.62 (18)
N1—C2—H2B111.3C50—C60—H60A109.5
C3—C2—H2B111.3C50—C60—H60B109.5
H2A—C2—H2B109.2H60A—C60—H60B109.5
N2—C3—C2102.88 (19)C50—C60—H60C109.5
N2—C3—H3A111.2H60A—C60—H60C109.5
C2—C3—H3A111.2H60B—C60—H60C109.5
N2—C3—H3B111.2C63—C62—C61120.4 (2)
C2—C3—H3B111.2C63—C62—H62119.8
H3A—C3—H3B109.1C61—C62—H62119.8
N3—C4—N4110.2 (2)C62—C63—C64120.1 (2)
N3—C4—S2124.90 (19)C62—C63—H63120.0
N4—C4—S2124.93 (19)C64—C63—H63120.0
N3—C5—C6102.7 (2)C65—C64—C63119.9 (2)
N3—C5—H5A111.2C65—C64—H64120.1
C6—C5—H5A111.2C63—C64—H64120.1
N3—C5—H5B111.2C64—C65—C66120.4 (2)
C6—C5—H5B111.2C64—C65—H65119.8
H5A—C5—H5B109.1C66—C65—H65119.8
N4—C6—C5102.9 (2)C65—C66—C61119.9 (2)
N4—C6—H6A111.2C65—C66—H66120.1
C5—C6—H6A111.2C61—C66—H66120.1
N4—C6—H6B111.2C76—C71—C72118.8 (2)
C5—C6—H6B111.2C76—C71—P3123.77 (19)
H6A—C6—H6B109.1C72—C71—P3117.33 (19)
N6—C7—N5109.7 (2)C73—C72—C71120.2 (3)
N6—C7—S3125.12 (19)C73—C72—H72119.9
N5—C7—S3125.2 (2)C71—C72—H72119.9
N5—C8—C9101.7 (2)C74—C73—C72120.3 (3)
N5—C8—H8A111.4C74—C73—H73119.8
C9—C8—H8A111.4C72—C73—H73119.8
N5—C8—H8B111.4C73—C74—C75119.9 (3)
C9—C8—H8B111.4C73—C74—H74120.1
H8A—C8—H8B109.3C75—C74—H74120.1
N6—C9—C8101.2 (2)C74—C75—C76120.0 (3)
N6—C9—H9A111.5C74—C75—H75120.0
C8—C9—H9A111.5C76—C75—H75120.0
N6—C9—H9B111.5C71—C76—C75120.8 (3)
C8—C9—H9B111.5C71—C76—H76119.6
H9A—C9—H9B109.4C75—C76—H76119.6
C16—C11—C12119.0 (2)C86—C81—C82119.3 (2)
C16—C11—P1117.51 (18)C86—C81—P3122.70 (18)
C12—C11—P1123.49 (18)C82—C81—P3118.02 (19)
C13—C12—C11120.6 (2)C83—C82—C81120.5 (3)
C13—C12—H12119.7C83—C82—H82119.7
C11—C12—H12119.7C81—C82—H82119.7
C14—C13—C12119.7 (2)C84—C83—C82119.9 (3)
C14—C13—H13120.2C84—C83—H83120.0
C12—C13—H13120.2C82—C83—H83120.0
C13—C14—C15120.1 (2)C85—C84—C83119.9 (3)
C13—C14—H14120.0C85—C84—H84120.0
C15—C14—H14120.0C83—C84—H84120.0
C14—C15—C16120.5 (3)C84—C85—C86120.6 (3)
C14—C15—H15119.7C84—C85—H85119.7
C16—C15—H15119.7C86—C85—H85119.7
C11—C16—C15120.0 (2)C81—C86—C85119.7 (2)
C11—C16—H16120.0C81—C86—H86120.1
C15—C16—H16120.0C85—C86—H86120.1
C22—C21—C26119.6 (2)C92—C91—C96119.3 (2)
C22—C21—P1122.98 (18)C92—C91—P3123.29 (18)
C26—C21—P1117.27 (17)C96—C91—P3117.23 (18)
C21—C22—C23120.0 (2)C93—C92—C91120.2 (2)
C21—C22—H22120.0C93—C92—H92119.9
C23—C22—H22120.0C91—C92—H92119.9
C24—C23—C22120.4 (2)C94—C93—C92120.0 (2)
C24—C23—H23119.8C94—C93—H93120.0
C22—C23—H23119.8C92—C93—H93120.0
C23—C24—C25119.7 (2)C95—C94—C93120.2 (2)
C23—C24—H24120.2C95—C94—H94119.9
C25—C24—H24120.2C93—C94—H94119.9
C24—C25—C26120.6 (2)C94—C95—C96120.0 (2)
C24—C25—H25119.7C94—C95—H95120.0
C26—C25—H25119.7C96—C95—H95120.0
C25—C26—C21119.6 (2)C95—C96—C91120.3 (2)
C25—C26—H26120.2C95—C96—H96119.9
C21—C26—H26120.2C91—C96—H96119.9
C32—C31—C36119.2 (2)C50—O4—Ag1132.75 (16)
C32—C31—P1123.68 (18)H7A—O7—H7B104 (3)
C36—C31—P1117.06 (17)H8C—O8—H8D99 (3)
O2—C30—O1124.5 (2)N7—C10—C20178.5 (3)
O2—C30—C40117.0 (2)C10—C20—H20A109.5
O1—C30—C40118.5 (2)C10—C20—H20B109.5
C31—C32—C33120.0 (2)H20A—C20—H20B109.5
C31—C32—H32120.0C10—C20—H20C109.5
C33—C32—H32120.0H20A—C20—H20C109.5
C34—C33—C32120.2 (2)H20B—C20—H20C109.5
C2—N1—C1—N20.9 (3)C41—C42—C43—C441.8 (4)
C2—N1—C1—S1177.63 (18)C42—C43—C44—C450.6 (4)
C3—N2—C1—N15.0 (3)C43—C44—C45—C461.0 (4)
C3—N2—C1—S1173.59 (18)C42—C41—C46—C450.1 (4)
Ag2—S1—C1—N122.0 (2)P2—C41—C46—C45175.3 (2)
Ag2i—S1—C1—N1129.75 (19)C44—C45—C46—C411.3 (4)
Ag2—S1—C1—N2159.64 (18)C41—P2—C51—C52164.80 (18)
Ag2i—S1—C1—N251.9 (2)C61—P2—C51—C5286.16 (19)
C1—N1—C2—C33.1 (3)Ag1—P2—C51—C5243.0 (2)
C1—N2—C3—C26.6 (3)C41—P2—C51—C5617.0 (2)
N1—C2—C3—N25.5 (3)C61—P2—C51—C5692.1 (2)
C5—N3—C4—N42.1 (3)Ag1—P2—C51—C56138.78 (19)
C5—N3—C4—S2176.5 (2)C56—C51—C52—C530.2 (4)
C6—N4—C4—N36.6 (3)P2—C51—C52—C53178.08 (19)
C6—N4—C4—S2174.8 (2)C51—C52—C53—C540.3 (4)
Ag2—S2—C4—N354.9 (2)C52—C53—C54—C550.1 (4)
Ag2—S2—C4—N4126.7 (2)C53—C54—C55—C560.1 (4)
C4—N3—C5—C69.1 (4)C54—C55—C56—C510.1 (4)
C4—N4—C6—C511.8 (3)C52—C51—C56—C550.0 (4)
N3—C5—C6—N411.9 (3)P2—C51—C56—C55178.18 (19)
C9—N6—C7—N57.6 (3)C51—P2—C61—C66156.93 (19)
C9—N6—C7—S3171.8 (2)C41—P2—C61—C6694.0 (2)
C8—N5—C7—N68.6 (3)Ag1—P2—C61—C6631.4 (2)
C8—N5—C7—S3172.0 (2)C51—P2—C61—C6221.0 (2)
Ag1—S3—C7—N623.8 (2)C41—P2—C61—C6288.0 (2)
Ag1—S3—C7—N5155.5 (2)Ag1—P2—C61—C62146.59 (17)
C7—N5—C8—C919.8 (3)C66—C61—C62—C630.5 (4)
C7—N6—C9—C819.2 (3)P2—C61—C62—C63177.46 (19)
N5—C8—C9—N622.1 (3)C61—C62—C63—C640.4 (4)
C21—P1—C11—C16160.75 (19)C62—C63—C64—C650.3 (4)
C31—P1—C11—C1691.2 (2)C63—C64—C65—C661.0 (4)
Ag2—P1—C11—C1632.7 (2)C64—C65—C66—C610.9 (4)
C21—P1—C11—C1220.0 (2)C62—C61—C66—C650.2 (4)
C31—P1—C11—C1288.0 (2)P2—C61—C66—C65178.2 (2)
Ag2—P1—C11—C12148.05 (18)C91—P3—C71—C7699.6 (2)
C16—C11—C12—C130.0 (4)C81—P3—C71—C768.6 (2)
P1—C11—C12—C13179.19 (19)Ag1—P3—C71—C76131.61 (19)
C11—C12—C13—C140.3 (4)C91—P3—C71—C7283.7 (2)
C12—C13—C14—C150.8 (4)C81—P3—C71—C72168.2 (2)
C13—C14—C15—C161.1 (4)Ag1—P3—C71—C7245.1 (2)
C12—C11—C16—C150.3 (4)C76—C71—C72—C730.2 (4)
P1—C11—C16—C15178.9 (2)P3—C71—C72—C73177.2 (2)
C14—C15—C16—C110.9 (4)C71—C72—C73—C740.7 (5)
C11—P1—C21—C2282.9 (2)C72—C73—C74—C751.0 (5)
C31—P1—C21—C2225.3 (2)C73—C74—C75—C760.7 (4)
Ag2—P1—C21—C22146.29 (18)C72—C71—C76—C750.0 (4)
C11—P1—C21—C2692.77 (19)P3—C71—C76—C75176.8 (2)
C31—P1—C21—C26159.03 (18)C74—C75—C76—C710.3 (4)
Ag2—P1—C21—C2638.0 (2)C91—P3—C81—C861.9 (2)
C26—C21—C22—C233.3 (4)C71—P3—C81—C86107.7 (2)
P1—C21—C22—C23172.32 (19)Ag1—P3—C81—C86128.2 (2)
C21—C22—C23—C241.5 (4)C91—P3—C81—C82176.4 (2)
C22—C23—C24—C251.0 (4)C71—P3—C81—C8274.0 (2)
C23—C24—C25—C261.8 (4)Ag1—P3—C81—C8250.1 (2)
C24—C25—C26—C210.1 (4)C86—C81—C82—C830.6 (4)
C22—C21—C26—C252.4 (4)P3—C81—C82—C83179.0 (2)
P1—C21—C26—C25173.39 (19)C81—C82—C83—C841.0 (5)
C11—P1—C31—C320.4 (2)C82—C83—C84—C850.6 (5)
C21—P1—C31—C32107.2 (2)C83—C84—C85—C860.2 (5)
Ag2—P1—C31—C32129.43 (18)C82—C81—C86—C850.1 (4)
C11—P1—C31—C36177.69 (18)P3—C81—C86—C85178.1 (2)
C21—P1—C31—C3674.73 (19)C84—C85—C86—C810.5 (5)
Ag2—P1—C31—C3648.66 (19)C71—P3—C91—C9225.0 (2)
C36—C31—C32—C330.2 (3)C81—P3—C91—C9283.4 (2)
P1—C31—C32—C33178.25 (19)Ag1—P3—C91—C92152.64 (17)
C31—C32—C33—C340.2 (4)C71—P3—C91—C96159.91 (19)
C32—C33—C34—C350.2 (4)C81—P3—C91—C9691.7 (2)
C33—C34—C35—C360.2 (4)Ag1—P3—C91—C9632.3 (2)
C34—C35—C36—C310.6 (4)C96—C91—C92—C931.5 (3)
C32—C31—C36—C350.6 (4)P3—C91—C92—C93173.51 (19)
P1—C31—C36—C35178.78 (19)C91—C92—C93—C941.1 (4)
C51—P2—C41—C46115.2 (2)C92—C93—C94—C952.5 (4)
C61—P2—C41—C467.7 (2)C93—C94—C95—C961.1 (4)
Ag1—P2—C41—C46122.04 (19)C94—C95—C96—C911.5 (4)
C51—P2—C41—C4269.4 (2)C92—C91—C96—C952.8 (4)
C61—P2—C41—C42176.87 (19)P3—C91—C96—C95172.5 (2)
Ag1—P2—C41—C4253.4 (2)O6—C50—O4—Ag180.3 (3)
C46—C41—C42—C431.4 (4)C60—C50—O4—Ag1101.4 (2)
P2—C41—C42—C43177.1 (2)
Symmetry code: (i) x, y, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O10.882.102.908 (3)153
N2—H2···O8ii0.882.002.808 (3)152
N3—H3···O10.881.942.780 (3)160
N4—H4···O2iii0.882.092.864 (3)146
N5—H5···O7iv0.881.962.767 (3)152
N6—H6···O40.881.912.780 (3)172
O7—H7A···O60.85 (1)1.88 (1)2.716 (3)169 (4)
O7—H7B···O6v0.84 (1)2.00 (2)2.782 (3)154 (3)
O8—H8C···O20.84 (1)1.88 (1)2.709 (3)167 (3)
O8—H8D···S2iv0.84 (1)2.56 (2)3.357 (2)159 (3)
Symmetry codes: (ii) x+1, y, z+1; (iii) x1, y, z; (iv) x+1, y, z; (v) x, y+1, z.
 

Acknowledgements

We are grateful to the Department of Chemistry, Faculty of Science, Prince of Songkla University, for financial assistance. We would like to thank Dr Matthias Zeller for collecting data at the Youngstown State University X-ray diffraction facility, funded in part by NSF grant DMR 1337296.

References

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