metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 70| Part 9| September 2014| Pages m337-m338

Crystal structure of (1,3-di­methyl­thio­urea-κS)tris­­(tri­phenyl­phosphane-κP)silver(I) acetate

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

Edited by M. Weil, Vienna University of Technology, Austria (Received 19 August 2014; accepted 22 August 2014; online 30 August 2014)

In the mononuclear title salt, [Ag(C3H8N2S)(C18H15P)3](CH3COO), the AgI ion exhibits a distorted tetra­hedral coordination sphere defined by three P atoms from three tri­phenyl­phosphane ligands and one S atom from a 1,3-di­­methyl­thio­urea ligand. In the crystal, the acetate anion is linked with the complex cation via duplex N—H⋯O hydrogen bonds [graph-set motif R22(8)].

1. Related literature

For studies of silver(I) complexes with tertiary phosphane and sulfur-donor ligands as co-ligands, see: McFarlane et al. (1998[McFarlane, W., Akrivos, P. D., Aslanidis, P., Karagiannidis, P., Hatzisymeon, C., Numan, M. & Kokkou, S. (1998). Inorg. Chim. Acta, 281, 121-125.]); Lobana et al. (2008[Lobana, T. S., Khanna, S., Hundal, G., Liaw, B.-J. & Liu, C. W. (2008). Polyhedron, 27, 2251-2258.]); Pakawatchai et al. (2012[Pakawatchai, C., Jantaramas, P., Mokhagul, J. & Nimthong, R. (2012). Acta Cryst. E68, m1506-m1507.]). For potential applications of silver(I) complexes, see: Isab et al. (2010[Isab, A. A., Nawaz, S., Saleem, M., Altaf, M., Monim-ul-Mehboob, M., Ahmad, S. & Evans, H. S. (2010). Polyhedron, 29, 1251-1256.]); 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 observed bond lengths distribution is in good agreement with related structures, such as [Ag2Cl2(μ-S-HL)2(PPh3)2] (HL = 2-benzoyl­pyridine thio­semicarbazone; Lobana et al., 2008[Lobana, T. S., Khanna, S., Hundal, G., Liaw, B.-J. & Liu, C. W. (2008). Polyhedron, 27, 2251-2258.]) and [Ag(C5H12N2S)(C18H15P)3](CH3COO)·CH3OH (Wattanakanjana et al., 2014[Wattanakanjana, Y., Nimthong, A. & Kamrod, C. (2014). Acta Cryst. E70, m216-m217.]). For graph-set analysis, see: Etter et al. (1990[Etter, M. C., MacDonald, J. C. & Bernstein, J. (1990). Acta Cryst. B46, 256-262.]).

[Scheme 1]

2. Experimental

2.1. Crystal data

  • [Ag(C3H8N2S)(C18H15P)3]C2H3O2

  • Mr = 1057.89

  • Monoclinic, P 21 /c

  • a = 15.780 (4) Å

  • b = 15.427 (4) Å

  • c = 21.649 (6) Å

  • β = 102.262 (5)°

  • V = 5150 (2) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.57 mm−1

  • T = 100 K

  • 0.15 × 0.09 × 0.07 mm

2.1.2. Data collection

  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2013[Bruker (2013). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.628, Tmax = 0.746

  • 26460 measured reflections

  • 11781 independent reflections

  • 7575 reflections with I > 2σ(I)

  • Rint = 0.074

2.1.3. Refinement

  • R[F2 > 2σ(F2)] = 0.053

  • wR(F2) = 0.106

  • S = 1.02

  • 11781 reflections

  • 616 parameters

  • H-atom parameters constrained

  • Δρmax = 0.80 e Å−3

  • Δρmin = −0.64 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N1—H1⋯O2 0.88 1.89 2.762 (4) 170
N2—H2⋯O1 0.88 1.91 2.773 (4) 166

Data collection: APEX2 (Bruker, 2013[Bruker (2013). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2013[Bruker (2013). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]) and SHELXLE (Hübschle et al., 2011[Hübschle, C. B., Sheldrick, G. M. & Dittrich, B. (2011). J. Appl. Cryst. 44, 1281-1284.]); molecular graphics: 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.]); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]) and publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).

Supporting information


Synthesis and crystallisation top

Tri­phenyl­phosphane, PPh3, (0.31 g) was dissolved in 30 ml of acetone at 338 K and then silver acetate, AgOAc, (0.10 g) was added. The mixture was stirred for 2 hr and then N,N'-di­methyl­thio­urea, dmtu, (0.07 g) was added and the new reaction mixture was heated under reflux for 4 hr during which the precipitate gradually disappeared. The resulting clear solution was filtered and left to evaporate at room temperature. The crystalline complex, which deposited upon standing for several days, was filtered off and dried in vacuo.

Refinement top

Reflections (002), (100), (111), (110), (102) and (011) were affected by the beam stop and were omitted from the refinement. H atoms bonded to C and N atoms were included in calculated positions and were refined with a riding model using distances of 0.95 Å (aryl H), 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).

Related literature top

For studies of silver(I) complexes with tertiary phosphane and sulfur-donor ligands as co-ligands, see: McFarlane et al. (1998); Lobana et al. (2008); Pakawatchai et al. (2012). For potential applications of silver(I) complexes, see: Isab et al. (2010); Ferrari et al. (2007). The observed bond lengths distribution is in good agreement with related structures, such as [Ag2Cl2(µ-S-HL)2(PPh3)2] (L = 2-benzoylpyridine thiosemicarbazone; Lobana et al., 2008) and [Ag(C5H12N2S)(C18H15P)3](CH3COO)·CH3OH (Wattanakanjana et al., 2014). For graph-set analysis, see: Etter et al. (1990).

Computing details top

Data collection: APEX2 (Bruker, 2013); cell refinement: SAINT (Bruker, 2013); data reduction: SAINT (Bruker, 2013); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008) and SHELXLE (Hübschle et al., 2011); molecular graphics: Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and publCIF (Westrip, 2010).

Figures top
[Figure 1] Fig. 1. The molecular entities of the title compound with displacement ellipsoids drawn at the 50% probability level. N—H···O hydrogen bonds are shown as red lines.
[Figure 2] Fig. 2. Packing plot of the molecular components of the title compound. N—H···O hydrogen bonds are shown as red lines.
(1,3-Dimethylthiourea-κS)tris(triphenylphosphane-κP)silver(I) acetate top
Crystal data top
[Ag(C3H8N2S)(C18H15P)3]C2H3O2F(000) = 2192
Mr = 1057.89Dx = 1.365 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 15.780 (4) ÅCell parameters from 2479 reflections
b = 15.427 (4) Åθ = 2.2–22.0°
c = 21.649 (6) ŵ = 0.57 mm1
β = 102.262 (5)°T = 100 K
V = 5150 (2) Å3Rod, colourless
Z = 40.15 × 0.09 × 0.07 mm
Data collection top
Bruker APEXII CCD
diffractometer
11781 independent reflections
Radiation source: fine focus sealed tube7575 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.074
ω and phi scansθmax = 27.5°, θmin = 2.3°
Absorption correction: multi-scan
(SADABS; Bruker, 2013)
h = 2017
Tmin = 0.628, Tmax = 0.746k = 2011
26460 measured reflectionsl = 2827
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)] = 0.053Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.106H-atom parameters constrained
S = 1.02 w = 1/[σ2(Fo2) + (0.0281P)2]
where P = (Fo2 + 2Fc2)/3
11781 reflections(Δ/σ)max = 0.001
616 parametersΔρmax = 0.80 e Å3
0 restraintsΔρmin = 0.64 e Å3
Crystal data top
[Ag(C3H8N2S)(C18H15P)3]C2H3O2V = 5150 (2) Å3
Mr = 1057.89Z = 4
Monoclinic, P21/cMo Kα radiation
a = 15.780 (4) ŵ = 0.57 mm1
b = 15.427 (4) ÅT = 100 K
c = 21.649 (6) Å0.15 × 0.09 × 0.07 mm
β = 102.262 (5)°
Data collection top
Bruker APEXII CCD
diffractometer
11781 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2013)
7575 reflections with I > 2σ(I)
Tmin = 0.628, Tmax = 0.746Rint = 0.074
26460 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0530 restraints
wR(F2) = 0.106H-atom parameters constrained
S = 1.02Δρmax = 0.80 e Å3
11781 reflectionsΔρmin = 0.64 e Å3
616 parameters
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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.3031 (2)0.5069 (3)0.94747 (18)0.0208 (9)
C20.4133 (3)0.5809 (3)0.9015 (2)0.0332 (11)
H2A0.40410.54660.86260.050*
H2B0.46190.55660.93250.050*
H2C0.42640.64100.89220.050*
C30.1888 (2)0.4489 (3)0.9976 (2)0.0248 (10)
H3A0.17750.40040.96770.037*
H3B0.13380.47051.00570.037*
H3C0.22580.42911.03730.037*
C40.1342 (2)0.4805 (2)0.75494 (18)0.0172 (9)
C50.1944 (3)0.5404 (3)0.78514 (19)0.0218 (9)
H50.23570.52390.82190.026*
C60.1950 (3)0.6247 (3)0.7622 (2)0.0278 (10)
H60.23570.66560.78380.033*
C70.1367 (3)0.6488 (3)0.7084 (2)0.0286 (11)
H70.13750.70620.69270.034*
C80.0771 (3)0.5900 (3)0.6772 (2)0.0282 (10)
H80.03700.60640.63980.034*
C90.0762 (3)0.5060 (3)0.70093 (19)0.0234 (10)
H90.03470.46550.67950.028*
C100.0642 (2)0.3820 (2)0.84535 (17)0.0139 (8)
C110.0312 (2)0.4598 (3)0.86199 (18)0.0216 (9)
H110.04530.51240.84360.026*
C120.0221 (3)0.4614 (3)0.9051 (2)0.0270 (10)
H120.04360.51530.91650.032*
C130.0442 (3)0.3862 (3)0.93169 (19)0.0253 (10)
H130.08170.38780.96070.030*
C140.0110 (2)0.3072 (3)0.91574 (19)0.0230 (9)
H140.02540.25480.93420.028*
C150.0422 (2)0.3058 (2)0.87344 (19)0.0211 (9)
H150.06470.25190.86290.025*
C160.0758 (2)0.3035 (2)0.72943 (17)0.0173 (9)
C170.0135 (2)0.3085 (3)0.71026 (18)0.0214 (9)
H170.04450.34950.72960.026*
C180.0583 (3)0.2549 (3)0.66341 (19)0.0258 (10)
H180.11960.25920.65070.031*
C190.0136 (3)0.1946 (3)0.63501 (19)0.0268 (10)
H190.04380.15830.60210.032*
C200.0756 (3)0.1878 (3)0.65507 (19)0.0249 (9)
H200.10640.14540.63680.030*
C210.1197 (3)0.2422 (2)0.70136 (18)0.0198 (9)
H210.18100.23770.71420.024*
C220.2110 (2)0.1580 (2)0.95183 (18)0.0174 (9)
C230.2183 (3)0.2192 (3)0.99953 (19)0.0256 (10)
H230.25740.26631.00100.031*
C240.1689 (3)0.2122 (3)1.0452 (2)0.0363 (12)
H240.17510.25401.07810.044*
C250.1110 (3)0.1451 (3)1.0433 (2)0.0363 (12)
H250.07680.14051.07430.044*
C260.1035 (3)0.0843 (3)0.9954 (2)0.0388 (12)
H260.06370.03770.99380.047*
C270.1534 (3)0.0903 (3)0.9494 (2)0.0298 (11)
H270.14770.04810.91670.036*
C280.2627 (2)0.0767 (2)0.84717 (17)0.0165 (9)
C290.1843 (3)0.0723 (3)0.80319 (19)0.0226 (9)
H290.14360.11810.80120.027*
C300.1646 (3)0.0031 (3)0.7625 (2)0.0275 (10)
H300.11090.00150.73260.033*
C310.2231 (3)0.0637 (3)0.7652 (2)0.0344 (12)
H310.20950.11190.73760.041*
C320.3015 (3)0.0607 (3)0.8080 (2)0.0378 (12)
H320.34190.10660.80940.045*
C330.3214 (3)0.0089 (3)0.8489 (2)0.0294 (11)
H330.37550.01050.87820.035*
C340.3878 (2)0.1533 (2)0.95073 (18)0.0159 (8)
C350.3990 (2)0.0966 (2)1.00142 (18)0.0173 (9)
H350.35150.06241.00770.021*
C360.4778 (3)0.0889 (2)1.04271 (19)0.0224 (9)
H360.48430.04951.07710.027*
C370.5479 (3)0.1383 (3)1.03452 (19)0.0229 (9)
H370.60210.13371.06360.027*
C380.5384 (3)0.1941 (3)0.98399 (19)0.0246 (10)
H380.58640.22750.97760.030*
C390.4592 (2)0.2016 (2)0.94246 (18)0.0190 (9)
H390.45330.24030.90770.023*
C400.3827 (2)0.2476 (2)0.70976 (17)0.0135 (8)
C410.3577 (2)0.1651 (2)0.72423 (19)0.0196 (9)
H410.34270.15460.76380.023*
C420.3547 (3)0.0980 (3)0.6812 (2)0.0235 (10)
H420.33730.04170.69130.028*
C430.3766 (3)0.1125 (3)0.6241 (2)0.0241 (10)
H430.37510.06600.59510.029*
C440.4007 (2)0.1943 (3)0.60837 (18)0.0221 (9)
H440.41510.20440.56850.026*
C450.4037 (2)0.2616 (2)0.65126 (17)0.0181 (9)
H450.42040.31790.64060.022*
C460.5064 (2)0.3314 (2)0.80672 (17)0.0143 (8)
C470.5333 (2)0.3744 (2)0.86439 (18)0.0184 (9)
H470.49200.40460.88240.022*
C480.6194 (3)0.3733 (2)0.89543 (19)0.0213 (9)
H480.63690.40330.93440.026*
C490.6805 (3)0.3290 (3)0.87027 (19)0.0249 (10)
H490.73950.32800.89190.030*
C500.6548 (3)0.2863 (3)0.8134 (2)0.0266 (10)
H500.69650.25620.79570.032*
C510.5687 (2)0.2867 (2)0.78180 (19)0.0198 (9)
H510.55190.25650.74290.024*
C520.3793 (2)0.4305 (2)0.71993 (17)0.0140 (8)
C530.4453 (3)0.4913 (2)0.72276 (19)0.0225 (9)
H530.49860.48460.75250.027*
C540.4326 (3)0.5617 (3)0.6817 (2)0.0287 (11)
H540.47730.60370.68420.034*
C550.3567 (3)0.5714 (3)0.6378 (2)0.0267 (10)
H550.34940.61910.60950.032*
C560.2910 (3)0.5114 (3)0.63488 (19)0.0233 (10)
H560.23810.51790.60470.028*
C570.3025 (3)0.4423 (2)0.67590 (18)0.0195 (9)
H570.25670.40170.67400.023*
C580.2149 (3)0.7483 (3)0.9683 (2)0.0267 (10)
C590.1905 (3)0.8391 (3)0.9867 (2)0.0456 (14)
H59A0.19600.84201.03260.068*
H59B0.13050.85180.96560.068*
H59C0.22930.88180.97380.068*
N10.3354 (2)0.5787 (2)0.92701 (16)0.0228 (8)
H10.30780.62780.92910.027*
N20.2324 (2)0.5181 (2)0.97095 (15)0.0206 (8)
H20.21070.57070.97030.025*
O10.17981 (18)0.68572 (18)0.99000 (14)0.0293 (7)
O20.26766 (18)0.74290 (17)0.93254 (15)0.0338 (8)
S10.35100 (6)0.40759 (7)0.94540 (5)0.0203 (2)
Ag10.28404 (2)0.31848 (2)0.84130 (2)0.01465 (8)
P10.13742 (6)0.37329 (6)0.79102 (5)0.0148 (2)
P20.28410 (6)0.17238 (6)0.89731 (5)0.0148 (2)
P30.39152 (6)0.33287 (6)0.76932 (5)0.0134 (2)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.015 (2)0.031 (3)0.015 (2)0.0006 (18)0.0013 (17)0.0036 (17)
C20.027 (3)0.035 (3)0.042 (3)0.009 (2)0.018 (2)0.002 (2)
C30.017 (2)0.032 (3)0.028 (2)0.0002 (19)0.0106 (19)0.0012 (19)
C40.021 (2)0.013 (2)0.020 (2)0.0042 (17)0.0114 (18)0.0023 (16)
C50.020 (2)0.024 (2)0.021 (2)0.0009 (18)0.0046 (18)0.0037 (18)
C60.031 (3)0.022 (2)0.030 (3)0.012 (2)0.007 (2)0.0001 (19)
C70.029 (3)0.020 (2)0.039 (3)0.0021 (19)0.012 (2)0.009 (2)
C80.025 (2)0.029 (3)0.029 (3)0.008 (2)0.001 (2)0.010 (2)
C90.017 (2)0.024 (2)0.029 (3)0.0029 (18)0.0028 (18)0.0006 (19)
C100.0069 (18)0.019 (2)0.015 (2)0.0000 (16)0.0014 (15)0.0007 (16)
C110.023 (2)0.022 (2)0.021 (2)0.0046 (18)0.0084 (18)0.0038 (18)
C120.034 (3)0.026 (3)0.026 (2)0.013 (2)0.016 (2)0.0048 (19)
C130.022 (2)0.033 (3)0.023 (2)0.004 (2)0.0097 (19)0.0022 (19)
C140.024 (2)0.024 (2)0.024 (2)0.0085 (19)0.0106 (18)0.0016 (18)
C150.022 (2)0.015 (2)0.027 (2)0.0023 (18)0.0071 (18)0.0020 (17)
C160.022 (2)0.015 (2)0.014 (2)0.0007 (17)0.0037 (16)0.0001 (16)
C170.017 (2)0.025 (2)0.021 (2)0.0038 (18)0.0029 (17)0.0003 (18)
C180.019 (2)0.034 (3)0.023 (2)0.005 (2)0.0021 (19)0.0062 (19)
C190.039 (3)0.024 (3)0.015 (2)0.011 (2)0.0001 (19)0.0026 (18)
C200.031 (2)0.018 (2)0.026 (2)0.001 (2)0.0070 (19)0.0037 (19)
C210.021 (2)0.017 (2)0.023 (2)0.0014 (17)0.0097 (18)0.0047 (17)
C220.0105 (19)0.022 (2)0.022 (2)0.0047 (16)0.0071 (16)0.0090 (17)
C230.026 (2)0.028 (3)0.026 (2)0.0024 (19)0.014 (2)0.0010 (19)
C240.042 (3)0.039 (3)0.034 (3)0.007 (2)0.021 (2)0.001 (2)
C250.032 (3)0.049 (3)0.037 (3)0.008 (2)0.027 (2)0.011 (2)
C260.030 (3)0.048 (3)0.044 (3)0.010 (2)0.018 (2)0.009 (2)
C270.026 (3)0.032 (3)0.033 (3)0.002 (2)0.010 (2)0.007 (2)
C280.022 (2)0.013 (2)0.015 (2)0.0021 (16)0.0058 (17)0.0035 (16)
C290.017 (2)0.024 (2)0.026 (2)0.0013 (18)0.0031 (18)0.0019 (18)
C300.026 (2)0.027 (3)0.027 (3)0.010 (2)0.000 (2)0.0022 (19)
C310.046 (3)0.025 (3)0.031 (3)0.007 (2)0.005 (2)0.008 (2)
C320.043 (3)0.028 (3)0.039 (3)0.013 (2)0.001 (2)0.008 (2)
C330.028 (2)0.027 (3)0.028 (3)0.013 (2)0.005 (2)0.0010 (19)
C340.017 (2)0.014 (2)0.016 (2)0.0057 (16)0.0024 (16)0.0000 (16)
C350.015 (2)0.018 (2)0.020 (2)0.0019 (17)0.0074 (17)0.0012 (17)
C360.025 (2)0.022 (2)0.020 (2)0.0068 (19)0.0032 (18)0.0050 (17)
C370.014 (2)0.029 (3)0.024 (2)0.0055 (18)0.0012 (18)0.0014 (18)
C380.017 (2)0.028 (3)0.029 (2)0.0015 (19)0.0063 (18)0.0013 (19)
C390.021 (2)0.021 (2)0.018 (2)0.0046 (17)0.0097 (17)0.0029 (16)
C400.0114 (19)0.019 (2)0.0108 (19)0.0037 (16)0.0030 (15)0.0006 (15)
C410.018 (2)0.021 (2)0.022 (2)0.0001 (17)0.0081 (17)0.0004 (17)
C420.023 (2)0.015 (2)0.035 (3)0.0020 (18)0.011 (2)0.0027 (19)
C430.023 (2)0.021 (2)0.026 (2)0.0083 (18)0.0019 (19)0.0124 (19)
C440.027 (2)0.024 (3)0.015 (2)0.0060 (19)0.0063 (17)0.0012 (17)
C450.021 (2)0.021 (2)0.014 (2)0.0030 (17)0.0071 (17)0.0015 (17)
C460.0123 (19)0.014 (2)0.016 (2)0.0003 (16)0.0020 (15)0.0034 (16)
C470.016 (2)0.019 (2)0.020 (2)0.0007 (17)0.0058 (17)0.0019 (17)
C480.024 (2)0.019 (2)0.018 (2)0.0077 (18)0.0014 (18)0.0023 (17)
C490.015 (2)0.028 (3)0.030 (2)0.0014 (19)0.0031 (18)0.012 (2)
C500.016 (2)0.033 (3)0.033 (3)0.0031 (19)0.0091 (19)0.001 (2)
C510.018 (2)0.019 (2)0.023 (2)0.0018 (17)0.0068 (18)0.0047 (17)
C520.017 (2)0.012 (2)0.016 (2)0.0026 (16)0.0097 (16)0.0023 (15)
C530.022 (2)0.016 (2)0.025 (2)0.0012 (18)0.0043 (18)0.0006 (17)
C540.033 (3)0.018 (2)0.034 (3)0.0036 (19)0.005 (2)0.0023 (19)
C550.040 (3)0.016 (2)0.024 (2)0.003 (2)0.007 (2)0.0083 (18)
C560.022 (2)0.028 (3)0.020 (2)0.0097 (19)0.0035 (18)0.0038 (18)
C570.021 (2)0.017 (2)0.021 (2)0.0014 (17)0.0066 (18)0.0022 (17)
C580.020 (2)0.025 (3)0.030 (3)0.001 (2)0.005 (2)0.007 (2)
C590.043 (3)0.031 (3)0.062 (4)0.001 (2)0.008 (3)0.014 (2)
N10.0183 (19)0.022 (2)0.031 (2)0.0017 (15)0.0126 (16)0.0025 (16)
N20.0160 (18)0.0199 (19)0.028 (2)0.0004 (15)0.0102 (15)0.0040 (15)
O10.0270 (16)0.0262 (17)0.0367 (18)0.0018 (14)0.0113 (14)0.0009 (14)
O20.0232 (17)0.0270 (18)0.053 (2)0.0014 (14)0.0129 (16)0.0016 (15)
S10.0204 (5)0.0248 (6)0.0158 (5)0.0024 (4)0.0040 (4)0.0058 (4)
Ag10.01253 (14)0.01663 (16)0.01532 (15)0.00167 (13)0.00415 (11)0.00066 (13)
P10.0119 (5)0.0173 (6)0.0155 (5)0.0021 (4)0.0034 (4)0.0004 (4)
P20.0115 (5)0.0176 (6)0.0161 (5)0.0016 (4)0.0047 (4)0.0027 (4)
P30.0133 (5)0.0142 (6)0.0137 (5)0.0003 (4)0.0048 (4)0.0001 (4)
Geometric parameters (Å, º) top
C1—N21.332 (5)C31—C321.379 (6)
C1—N11.334 (5)C31—H310.9500
C1—S11.714 (4)C32—C331.384 (6)
C2—N11.450 (5)C32—H320.9500
C2—H2A0.9800C33—H330.9500
C2—H2B0.9800C34—C351.385 (5)
C2—H2C0.9800C34—C391.394 (5)
C3—N21.454 (5)C34—P21.816 (4)
C3—H3A0.9800C35—C361.373 (5)
C3—H3B0.9800C35—H350.9500
C3—H3C0.9800C36—C371.385 (5)
C4—C91.381 (5)C36—H360.9500
C4—C51.386 (5)C37—C381.375 (5)
C4—P11.825 (4)C37—H370.9500
C5—C61.393 (5)C38—C391.380 (5)
C5—H50.9500C38—H380.9500
C6—C71.372 (6)C39—H390.9500
C6—H60.9500C40—C411.388 (5)
C7—C81.376 (6)C40—C451.393 (5)
C7—H70.9500C40—P31.826 (4)
C8—C91.395 (5)C41—C421.387 (5)
C8—H80.9500C41—H410.9500
C9—H90.9500C42—C431.371 (5)
C10—C111.386 (5)C42—H420.9500
C10—C151.401 (5)C43—C441.380 (5)
C10—P11.820 (4)C43—H430.9500
C11—C121.383 (5)C44—C451.387 (5)
C11—H110.9500C44—H440.9500
C12—C131.373 (5)C45—H450.9500
C12—H120.9500C46—C471.398 (5)
C13—C141.397 (5)C46—C511.399 (5)
C13—H130.9500C46—P31.822 (4)
C14—C151.368 (5)C47—C481.382 (5)
C14—H140.9500C47—H470.9500
C15—H150.9500C48—C491.384 (5)
C16—C171.385 (5)C48—H480.9500
C16—C211.386 (5)C49—C501.379 (6)
C16—P11.825 (4)C49—H490.9500
C17—C181.382 (5)C50—C511.384 (5)
C17—H170.9500C50—H500.9500
C18—C191.388 (5)C51—H510.9500
C18—H180.9500C52—C571.386 (5)
C19—C201.385 (6)C52—C531.393 (5)
C19—H190.9500C52—P31.833 (4)
C20—C211.378 (5)C53—C541.390 (5)
C20—H200.9500C53—H530.9500
C21—H210.9500C54—C551.370 (6)
C22—C271.378 (5)C54—H540.9500
C22—C231.386 (5)C55—C561.381 (5)
C22—P21.831 (4)C55—H550.9500
C23—C241.387 (6)C56—C571.375 (5)
C23—H230.9500C56—H560.9500
C24—C251.375 (6)C57—H570.9500
C24—H240.9500C58—O11.252 (5)
C25—C261.384 (6)C58—O21.255 (5)
C25—H250.9500C58—C591.529 (6)
C26—C271.399 (6)C59—H59A0.9800
C26—H260.9500C59—H59B0.9800
C27—H270.9500C59—H59C0.9800
C28—C291.392 (5)N1—H10.8800
C28—C331.393 (5)N2—H20.8800
C28—P21.821 (4)S1—Ag12.6595 (11)
C29—C301.377 (5)Ag1—P12.4866 (11)
C29—H290.9500Ag1—P32.5450 (11)
C30—C311.376 (6)Ag1—P22.5592 (11)
C30—H300.9500
N2—C1—N1115.5 (4)C36—C35—H35119.5
N2—C1—S1122.4 (3)C34—C35—H35119.5
N1—C1—S1122.1 (3)C35—C36—C37120.4 (4)
N1—C2—H2A109.5C35—C36—H36119.8
N1—C2—H2B109.5C37—C36—H36119.8
H2A—C2—H2B109.5C38—C37—C36119.4 (4)
N1—C2—H2C109.5C38—C37—H37120.3
H2A—C2—H2C109.5C36—C37—H37120.3
H2B—C2—H2C109.5C37—C38—C39120.1 (4)
N2—C3—H3A109.5C37—C38—H38119.9
N2—C3—H3B109.5C39—C38—H38119.9
H3A—C3—H3B109.5C38—C39—C34121.1 (4)
N2—C3—H3C109.5C38—C39—H39119.5
H3A—C3—H3C109.5C34—C39—H39119.5
H3B—C3—H3C109.5C41—C40—C45118.8 (3)
C9—C4—C5118.3 (4)C41—C40—P3118.9 (3)
C9—C4—P1125.0 (3)C45—C40—P3122.2 (3)
C5—C4—P1116.7 (3)C42—C41—C40120.3 (4)
C4—C5—C6120.7 (4)C42—C41—H41119.9
C4—C5—H5119.6C40—C41—H41119.9
C6—C5—H5119.6C43—C42—C41120.3 (4)
C7—C6—C5120.0 (4)C43—C42—H42119.9
C7—C6—H6120.0C41—C42—H42119.9
C5—C6—H6120.0C42—C43—C44120.5 (4)
C6—C7—C8120.2 (4)C42—C43—H43119.8
C6—C7—H7119.9C44—C43—H43119.8
C8—C7—H7119.9C43—C44—C45119.4 (4)
C7—C8—C9119.4 (4)C43—C44—H44120.3
C7—C8—H8120.3C45—C44—H44120.3
C9—C8—H8120.3C44—C45—C40120.8 (4)
C4—C9—C8121.3 (4)C44—C45—H45119.6
C4—C9—H9119.4C40—C45—H45119.6
C8—C9—H9119.4C47—C46—C51118.2 (3)
C11—C10—C15118.2 (4)C47—C46—P3118.4 (3)
C11—C10—P1123.8 (3)C51—C46—P3123.3 (3)
C15—C10—P1117.9 (3)C48—C47—C46120.6 (4)
C12—C11—C10120.4 (4)C48—C47—H47119.7
C12—C11—H11119.8C46—C47—H47119.7
C10—C11—H11119.8C47—C48—C49120.6 (4)
C13—C12—C11120.9 (4)C47—C48—H48119.7
C13—C12—H12119.6C49—C48—H48119.7
C11—C12—H12119.6C50—C49—C48119.3 (4)
C12—C13—C14119.4 (4)C50—C49—H49120.3
C12—C13—H13120.3C48—C49—H49120.3
C14—C13—H13120.3C49—C50—C51120.7 (4)
C15—C14—C13119.6 (4)C49—C50—H50119.7
C15—C14—H14120.2C51—C50—H50119.7
C13—C14—H14120.2C50—C51—C46120.5 (4)
C14—C15—C10121.4 (4)C50—C51—H51119.7
C14—C15—H15119.3C46—C51—H51119.7
C10—C15—H15119.3C57—C52—C53118.6 (3)
C17—C16—C21118.6 (4)C57—C52—P3118.5 (3)
C17—C16—P1122.4 (3)C53—C52—P3122.8 (3)
C21—C16—P1119.0 (3)C54—C53—C52119.5 (4)
C18—C17—C16121.1 (4)C54—C53—H53120.2
C18—C17—H17119.5C52—C53—H53120.2
C16—C17—H17119.5C55—C54—C53121.0 (4)
C17—C18—C19119.8 (4)C55—C54—H54119.5
C17—C18—H18120.1C53—C54—H54119.5
C19—C18—H18120.1C54—C55—C56119.7 (4)
C20—C19—C18119.3 (4)C54—C55—H55120.1
C20—C19—H19120.3C56—C55—H55120.1
C18—C19—H19120.3C57—C56—C55119.7 (4)
C21—C20—C19120.3 (4)C57—C56—H56120.1
C21—C20—H20119.8C55—C56—H56120.1
C19—C20—H20119.8C56—C57—C52121.5 (4)
C20—C21—C16120.8 (4)C56—C57—H57119.3
C20—C21—H21119.6C52—C57—H57119.3
C16—C21—H21119.6O1—C58—O2125.8 (4)
C27—C22—C23119.7 (4)O1—C58—C59116.9 (4)
C27—C22—P2124.6 (3)O2—C58—C59117.3 (4)
C23—C22—P2115.7 (3)C58—C59—H59A109.5
C22—C23—C24120.6 (4)C58—C59—H59B109.5
C22—C23—H23119.7H59A—C59—H59B109.5
C24—C23—H23119.7C58—C59—H59C109.5
C25—C24—C23120.4 (4)H59A—C59—H59C109.5
C25—C24—H24119.8H59B—C59—H59C109.5
C23—C24—H24119.8C1—N1—C2124.1 (3)
C24—C25—C26119.0 (4)C1—N1—H1117.9
C24—C25—H25120.5C2—N1—H1117.9
C26—C25—H25120.5C1—N2—C3124.2 (3)
C25—C26—C27121.1 (4)C1—N2—H2117.9
C25—C26—H26119.4C3—N2—H2117.9
C27—C26—H26119.4C1—S1—Ag1112.73 (13)
C22—C27—C26119.3 (4)P1—Ag1—P3112.42 (4)
C22—C27—H27120.4P1—Ag1—P2114.42 (3)
C26—C27—H27120.4P3—Ag1—P2115.70 (3)
C29—C28—C33118.1 (4)P1—Ag1—S1111.13 (3)
C29—C28—P2118.2 (3)P3—Ag1—S1106.10 (4)
C33—C28—P2123.7 (3)P2—Ag1—S195.37 (4)
C30—C29—C28121.5 (4)C10—P1—C4104.26 (17)
C30—C29—H29119.3C10—P1—C16101.70 (17)
C28—C29—H29119.3C4—P1—C16105.06 (17)
C31—C30—C29119.6 (4)C10—P1—Ag1113.68 (12)
C31—C30—H30120.2C4—P1—Ag1115.71 (13)
C29—C30—H30120.2C16—P1—Ag1114.90 (13)
C30—C31—C32120.1 (4)C34—P2—C28106.06 (17)
C30—C31—H31119.9C34—P2—C22100.12 (17)
C32—C31—H31119.9C28—P2—C22102.89 (18)
C31—C32—C33120.3 (4)C34—P2—Ag1110.73 (12)
C31—C32—H32119.9C28—P2—Ag1116.76 (12)
C33—C32—H32119.9C22—P2—Ag1118.39 (12)
C32—C33—C28120.4 (4)C46—P3—C40102.97 (16)
C32—C33—H33119.8C46—P3—C52103.96 (17)
C28—C33—H33119.8C40—P3—C52101.36 (17)
C35—C34—C39117.9 (3)C46—P3—Ag1117.15 (12)
C35—C34—P2123.6 (3)C40—P3—Ag1114.11 (12)
C39—C34—P2118.4 (3)C52—P3—Ag1115.31 (12)
C36—C35—C34121.1 (4)
C9—C4—C5—C61.2 (6)C52—C53—C54—C551.2 (6)
P1—C4—C5—C6177.9 (3)C53—C54—C55—C561.3 (7)
C4—C5—C6—C71.3 (6)C54—C55—C56—C570.3 (6)
C5—C6—C7—C80.4 (7)C55—C56—C57—C520.8 (6)
C6—C7—C8—C90.4 (6)C53—C52—C57—C560.9 (6)
C5—C4—C9—C80.4 (6)P3—C52—C57—C56176.2 (3)
P1—C4—C9—C8178.7 (3)N2—C1—N1—C2178.2 (4)
C7—C8—C9—C40.5 (6)S1—C1—N1—C20.3 (6)
C15—C10—C11—C120.1 (6)N1—C1—N2—C3177.9 (3)
P1—C10—C11—C12178.0 (3)S1—C1—N2—C30.6 (5)
C10—C11—C12—C130.8 (6)N2—C1—S1—Ag187.7 (3)
C11—C12—C13—C141.2 (6)N1—C1—S1—Ag193.9 (3)
C12—C13—C14—C150.7 (6)C11—C10—P1—C411.8 (4)
C13—C14—C15—C100.2 (6)C15—C10—P1—C4170.3 (3)
C11—C10—C15—C140.6 (6)C11—C10—P1—C16120.8 (3)
P1—C10—C15—C14178.6 (3)C15—C10—P1—C1661.3 (3)
C21—C16—C17—C181.1 (6)C11—C10—P1—Ag1115.1 (3)
P1—C16—C17—C18179.9 (3)C15—C10—P1—Ag162.8 (3)
C16—C17—C18—C190.2 (6)C9—C4—P1—C1089.0 (4)
C17—C18—C19—C201.3 (6)C5—C4—P1—C1090.0 (3)
C18—C19—C20—C212.0 (6)C9—C4—P1—C1617.5 (4)
C19—C20—C21—C161.2 (6)C5—C4—P1—C16163.4 (3)
C17—C16—C21—C200.4 (6)C9—C4—P1—Ag1145.4 (3)
P1—C16—C21—C20179.4 (3)C5—C4—P1—Ag135.6 (3)
C27—C22—C23—C240.8 (6)C17—C16—P1—C1036.4 (4)
P2—C22—C23—C24177.0 (3)C21—C16—P1—C10142.6 (3)
C22—C23—C24—C251.0 (7)C17—C16—P1—C472.0 (3)
C23—C24—C25—C260.6 (7)C21—C16—P1—C4109.0 (3)
C24—C25—C26—C270.1 (7)C17—C16—P1—Ag1159.7 (3)
C23—C22—C27—C260.3 (6)C21—C16—P1—Ag119.3 (3)
P2—C22—C27—C26177.3 (3)C35—C34—P2—C2874.3 (4)
C25—C26—C27—C220.0 (7)C39—C34—P2—C28109.2 (3)
C33—C28—C29—C300.3 (6)C35—C34—P2—C2232.4 (4)
P2—C28—C29—C30178.2 (3)C39—C34—P2—C22144.1 (3)
C28—C29—C30—C310.4 (6)C35—C34—P2—Ag1158.1 (3)
C29—C30—C31—C320.8 (7)C39—C34—P2—Ag118.4 (3)
C30—C31—C32—C330.7 (7)C29—C28—P2—C34177.1 (3)
C31—C32—C33—C280.1 (7)C33—C28—P2—C345.1 (4)
C29—C28—C33—C320.4 (6)C29—C28—P2—C2272.4 (3)
P2—C28—C33—C32178.2 (3)C33—C28—P2—C22109.8 (4)
C39—C34—C35—C360.8 (6)C29—C28—P2—Ag159.0 (3)
P2—C34—C35—C36175.7 (3)C33—C28—P2—Ag1118.7 (3)
C34—C35—C36—C370.2 (6)C27—C22—P2—C34111.7 (4)
C35—C36—C37—C381.1 (6)C23—C22—P2—C3465.9 (3)
C36—C37—C38—C391.0 (6)C27—C22—P2—C282.5 (4)
C37—C38—C39—C340.0 (6)C23—C22—P2—C28175.2 (3)
C35—C34—C39—C380.9 (6)C27—C22—P2—Ag1128.0 (3)
P2—C34—C39—C38175.8 (3)C23—C22—P2—Ag154.4 (3)
C45—C40—C41—C420.5 (5)C47—C46—P3—C40165.2 (3)
P3—C40—C41—C42176.7 (3)C51—C46—P3—C4012.4 (4)
C40—C41—C42—C430.3 (6)C47—C46—P3—C5289.4 (3)
C41—C42—C43—C440.9 (6)C51—C46—P3—C5293.0 (3)
C42—C43—C44—C450.9 (6)C47—C46—P3—Ag139.1 (3)
C43—C44—C45—C400.1 (6)C51—C46—P3—Ag1138.5 (3)
C41—C40—C45—C440.5 (5)C41—C40—P3—C4695.5 (3)
P3—C40—C45—C44176.6 (3)C45—C40—P3—C4681.6 (3)
C51—C46—C47—C480.6 (6)C41—C40—P3—C52157.1 (3)
P3—C46—C47—C48178.4 (3)C45—C40—P3—C5225.8 (3)
C46—C47—C48—C490.6 (6)C41—C40—P3—Ag132.5 (3)
C47—C48—C49—C500.6 (6)C45—C40—P3—Ag1150.4 (3)
C48—C49—C50—C510.6 (6)C57—C52—P3—C46168.2 (3)
C49—C50—C51—C460.7 (6)C53—C52—P3—C468.8 (4)
C47—C46—C51—C500.7 (6)C57—C52—P3—C4061.6 (3)
P3—C46—C51—C50178.3 (3)C53—C52—P3—C40115.4 (3)
C57—C52—C53—C540.1 (6)C57—C52—P3—Ag162.2 (3)
P3—C52—C53—C54177.0 (3)C53—C52—P3—Ag1120.8 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O20.881.892.762 (4)170
N2—H2···O10.881.912.773 (4)166
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O20.881.892.762 (4)169.6
N2—H2···O10.881.912.773 (4)165.7
 

Acknowledgements

Financial support from the Department of Chemistry, Prince of Songkla University, is gratefully acknowledged. We would like to thank Dr Matthias Zeller for valuable suggestions and assistance with the X-ray structure determination and use of structure refinement programs.

References

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Volume 70| Part 9| September 2014| Pages m337-m338
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