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

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ISSN: 2414-3146

(Thio­cyanato-κS)tris­­(tri­phenyl­phosphane-κP)silver(I)

aDepartment of Chemistry, Boston University, Massachusetts 02215, 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 E. R. T. Tiekink, Sunway University, Malaysia (Received 12 August 2017; accepted 15 August 2017; online 21 August 2017)

In the mononuclear title complex, [Ag(SCN)(C18H15P)3], the AgI center is in a slightly distorted tetra­hedral coordination geometry formed by one S atom from a terminal thio­cyanate ligand and three P atoms from three tri­phenyl­phosphane ligands. In the crystal, weak C—H⋯N hydrogen bonds connect mol­ecules into a two-dimensional network parallel to (10[\overline{1}]). One of the phenyl rings is disordered over two positions which were refined with an occupancy ratio of 0.715 (16):0.285 (16).

3D view (loading...)
[Scheme 3D1]
Chemical scheme
[Scheme 1]

Structure description

Silver(I) complexes with phospho­rus and sulfur donor ligands have been of increasing inter­est because of the variety of their biological properties such as antibacterial, anti-inflammatory (Papanikolaou et al., 2015[Papanikolaou, P. A., Papadopoulos, A. G., Andreadou, E. G., Hatzidimitriou, A., Cox, P. J., Pantazaki, A. A. & Aslanidis, P. (2015). New J. Chem. 39, 4830-4844.]) and antitumor (Liu et al., 2008[Liu, J. J., Galettis, P., Farr, A., Maharaj, L., Samarasinha, H., McGechan, A. C., Baguley, B. C., Bowen, R. J., Berners-Price, S. J. & McKeage, M. J. (2008). J. Inorg. Biochem. 102, 303-310.]), as well as showing inter­esting luminescence 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.]). Herein, we report the crystal structure of a silver(I) thio­cyanate complex containing tri­phenyl­phosphane. The title complex was prepared by reacting silver(I) thio­cyanate and tri­phenyl­phosphane (PPh3), followed by the addition of 1-(4-nitro­phen­yl)-2-thio­urea, NPTU, in aceto­nitrile. An unexpected complex, [Ag(C18H15P)3(SCN)], was formed in high yield (74%) with no NPTU (Fig. 1[link]). In the mononuclear complex, the AgI center is in a slightly distorted tetra­hedral coordination geometry formed by one S atom from the terminal thio­cyanate ligand, and three P atoms from three tri­phenyl­phosphane ligands. The Ag—S bond length of 2.6128 (3) Å is slightly shorter than in [Ag(SCN){P(4-MeC6H4)3}3] [2.6613 (7) Å; Omondi et al., 2009[Omondi, B., Venter, G. J. S., Roodt, A. & Meijboom, R. (2009). Acta Cryst. B65, 699-706.]]. The angles at the AgI ion vary from 94.327 (10)° to 117.910 (10)°. In the crystal, the mol­ecules are connected via weak C3—H3⋯N1i, C40—H40⋯N1ii and C46—H46⋯N1iii hydrogen bonds, leading to the formation of a two-dimensional network parallel to (10[\overline{1}]) (Fig. 2[link] and Table 1[link]).

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
C3—H3⋯N1i 0.95 2.63 3.2987 (19) 128
C40—H40⋯N1ii 0.95 2.68 3.5540 (18) 153
C46—H46⋯N1iii 0.95 2.52 3.3460 (18) 145
Symmetry codes: (i) -x+1, -y, -z; (ii) [x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]; (iii) -x+1, -y+1, -z.
[Figure 1]
Figure 1
The mol­ecular structure, with displacement ellipsoids drawn at the 50% probability level. All H atoms and disordered component have been omitted for clarity.
[Figure 2]
Figure 2
Part of the crystal structure, showing the inter­molecular C—H⋯N hydrogen bonds (shown as dashed lines) leading to the formation of a two-dimensional network parallel to (10[\overline{1}]).

Synthesis and crystallization

Tri­phenyl­phosphane, PPh3 (0.27 g, 1.03 mmol) was dissolved in aceto­nitrile (30 ml) at 339 K and then silver(I) thio­cyanate, AgSCN (0.08 g, 0.48 mmol) was added. The mixture was stirred for 3 h after which 1-(4-nitro­phen­yl)-2-thio­urea, NPTU (0.1 g, 0.51 mmol) was added. The resulting reaction mixture was heated under reflux for 6 h during which time the precipitate gradually disappeared. The resulting yellow solution was filtered and left to evaporate at room temperature. The crystalline complex, which deposited upon standing after a few days, was filtered off and dried in vacuo (0.24 g, 74% yield). M.p. 445–447 K. IR bands (KBr, cm−1): 3375 (m), 3292 (w), 3179 (m), 3002 (w), 2368 (m), 2345 (m), 1509 (w), 1340 (s), 1243 (m), 1109 (m), 1056 (m), 879 (w), 830 (w), 808 (m), 748 (w), 692 (m), 511 (w), 418 (m).

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2[link]. A number of reflections. i.e. ([\overline{2}]02), ([\overline{2}]11), (012), (112), (202), (210), (141), ([\overline{1}]12), ([\overline{1}]21), (13,17,6), (16,13,10), ([\overline{9}],18,6), (5,4,12), (12,18,5), (14,15,10), (344), (571), (15,16,1), ([\overline{8}],19,3), (13,17,4), (103), (9,9,22), (9,7,15), (7,5,17), (5,4,10), (11,12,19), (234), ([\overline{5}],13,3) and (13,17,0) were omitted from the final refinement owing to poor agreement. Disorder in one of the phenyl was resolved over two positions with a refined occupancy ratio of 0.715 (16):0.285 (16). The C13/C13B atoms were common to both orientations. The Uij components of the ADP's were restrained to be similar for atoms closer to each other than 1.7 Å (SIMU).

Table 2
Experimental details

Crystal data
Chemical formula [Ag(NCS)(C18H15P)3]
Mr 952.76
Crystal system, space group Monoclinic, P21/n
Temperature (K) 100
a, b, c (Å) 18.1884 (10), 13.5886 (7), 18.3224 (10)
β (°) 94.711 (2)
V3) 4513.2 (4)
Z 4
Radiation type Mo Kα
μ (mm−1) 0.64
Crystal size (mm) 0.55 × 0.45 × 0.40
 
Data collection
Diffractometer Bruker AXS D8 Quest CMOS
Absorption correction Multi-scan (APEX3; Bruker, 2016[Bruker (2016). APEX3 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.])
Tmin, Tmax 0.673, 0.747
No. of measured, independent and observed [I > 2σ(I)] reflections 35349, 18408, 16598
Rint 0.014
(sin θ/λ)max−1) 0.834
 
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.027, 0.068, 1.06
No. of reflections 18408
No. of parameters 597
No. of restraints 192
H-atom treatment H-atom parameters constrained
Δρmax, Δρmin (e Å−3) 0.88, −0.95
Computer programs: APEX3 and SAINT (Bruker, 2016[Bruker (2016). APEX3 and SAINT. 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.]), 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.]).

Structural data


Computing details top

Data collection: APEX3 (Bruker, 2016); cell refinement: SAINT (Bruker, 2016); data reduction: SAINT (Bruker, 2016); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: Mercury (Macrae et al., 2008); software used to prepare material for publication: publCIF (Westrip, 2010).

(Thiocyanato-κS)tris(triphenylphosphane-κP)silver(I) top
Crystal data top
[Ag(NCS)(C18H15P)3]F(000) = 1960
Mr = 952.76Dx = 1.402 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 18.1884 (10) ÅCell parameters from 9970 reflections
b = 13.5886 (7) Åθ = 3.4–36.3°
c = 18.3224 (10) ŵ = 0.64 mm1
β = 94.711 (2)°T = 100 K
V = 4513.2 (4) Å3Block, colourless
Z = 40.55 × 0.45 × 0.40 mm
Data collection top
Bruker AXS D8 Quest CMOS
diffractometer
18408 independent reflections
Radiation source: sealed tube X-ray source16598 reflections with I > 2σ(I)
Triumph curved graphite crystal monochromatorRint = 0.014
ω and φi scansθmax = 36.4°, θmin = 3.2°
Absorption correction: multi-scan
(APEX3; Bruker, 2016)
h = 2230
Tmin = 0.673, Tmax = 0.747k = 1821
35349 measured reflectionsl = 3017
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.027H-atom parameters constrained
wR(F2) = 0.068 w = 1/[σ2(Fo2) + (0.0152P)2 + 3.9007P]
where P = (Fo2 + 2Fc2)/3
S = 1.06(Δ/σ)max = 0.002
18408 reflectionsΔρmax = 0.88 e Å3
597 parametersΔρmin = 0.95 e Å3
192 restraintsExtinction correction: SHELXL2014 (Sheldrick, 2015), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.000262
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.

Refinement. One phenyl ring was refined as disordered. The two moieties were restrained to have similar geometries and Uij components of ADPs were restrained to be similar for atoms closer than 1.7 Angstrom. The ipso carbon atom was not included in the disorder. Occupancies refined to 0.715 (16) to 0.28 (5).

All H atoms attached to carbon atoms were positioned geometrically and constrained to ride on their parent atoms, with C—H = 0.95 Å. Uiso(H) values were set to 1.2Ueq(C).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
Ag10.26601 (2)0.17828 (2)0.00411 (2)0.01458 (2)
S10.32976 (2)0.25597 (3)0.12349 (2)0.02206 (6)
P10.23375 (2)0.00665 (2)0.04613 (2)0.01421 (5)
P20.15358 (2)0.30707 (2)0.00563 (2)0.01333 (5)
P30.33118 (2)0.18985 (2)0.11004 (2)0.01245 (5)
N10.47680 (7)0.29965 (10)0.09709 (9)0.0324 (3)
C10.30071 (6)0.09262 (8)0.04243 (6)0.01542 (18)
C20.33764 (7)0.10148 (9)0.02128 (6)0.01743 (19)
H20.32740.05620.06030.021*
C30.38914 (7)0.17563 (9)0.02825 (6)0.01842 (19)
H30.41370.18100.07190.022*
C40.40473 (7)0.24203 (9)0.02873 (6)0.0188 (2)
H40.44010.29270.02430.023*
C50.36828 (7)0.23374 (9)0.09211 (6)0.0204 (2)
H50.37890.27910.13100.024*
C60.31640 (7)0.15979 (9)0.09935 (6)0.0186 (2)
H60.29170.15500.14290.022*
C70.20648 (6)0.00109 (8)0.13949 (6)0.01578 (18)
C80.25345 (7)0.04010 (11)0.19551 (6)0.0237 (2)
H80.29860.06950.18440.028*
C90.23452 (8)0.03820 (11)0.26750 (7)0.0265 (3)
H90.26690.06570.30540.032*
C100.16826 (7)0.00397 (10)0.28404 (6)0.0219 (2)
H100.15490.00430.33310.026*
C110.12191 (7)0.04540 (10)0.22893 (7)0.0228 (2)
H110.07680.07450.24030.027*
C120.14089 (7)0.04478 (10)0.15683 (6)0.0199 (2)
H120.10900.07430.11940.024*
C130.15535 (7)0.03948 (9)0.01221 (6)0.0184 (2)0.715 (16)
C140.1448 (3)0.1397 (3)0.0261 (3)0.0286 (7)0.715 (16)
H140.17710.18680.00230.034*0.715 (16)
C150.0864 (3)0.1706 (4)0.0751 (3)0.0370 (8)0.715 (16)
H150.07940.23870.08490.044*0.715 (16)
C160.0392 (3)0.1035 (5)0.1090 (4)0.0366 (10)0.715 (16)
H160.00110.12530.14130.044*0.715 (16)
C170.0501 (2)0.0039 (4)0.0965 (3)0.0346 (8)0.715 (16)
H170.01790.04280.12100.041*0.715 (16)
C180.1081 (2)0.0278 (3)0.0481 (3)0.0255 (6)0.715 (16)
H180.11530.09620.03950.031*0.715 (16)
C13B0.15535 (7)0.03948 (9)0.01221 (6)0.0184 (2)0.285 (16)
C14B0.1464 (7)0.1320 (8)0.0427 (6)0.0288 (16)0.285 (16)
H14B0.18280.18120.03210.035*0.285 (16)
C15B0.0837 (8)0.1532 (10)0.0892 (7)0.0358 (18)0.285 (16)
H15B0.07740.21740.10930.043*0.285 (16)
C16B0.0310 (10)0.0830 (11)0.1064 (11)0.0330 (19)0.285 (16)
H16B0.01040.09780.13960.040*0.285 (16)
C17B0.0383 (6)0.0084 (7)0.0754 (7)0.0328 (16)0.285 (16)
H17B0.00110.05660.08570.039*0.285 (16)
C18B0.1000 (6)0.0306 (8)0.0291 (7)0.0275 (15)0.285 (16)
H18B0.10490.09450.00830.033*0.285 (16)
C190.12105 (6)0.32699 (9)0.08470 (6)0.01555 (18)
C200.13199 (7)0.25301 (9)0.13697 (6)0.01797 (19)
H200.15580.19360.12500.022*
C210.10814 (8)0.26562 (10)0.20675 (6)0.0229 (2)
H210.11580.21480.24210.027*
C220.07325 (8)0.35212 (10)0.22482 (6)0.0230 (2)
H220.05670.36040.27230.028*
C230.06272 (8)0.42658 (10)0.17301 (7)0.0242 (2)
H230.03900.48590.18510.029*
C240.08678 (7)0.41458 (10)0.10358 (6)0.0217 (2)
H240.07990.46610.06870.026*
C250.06837 (6)0.29596 (9)0.06609 (6)0.01584 (18)
C260.00128 (7)0.32053 (12)0.04485 (7)0.0263 (3)
H260.00640.34220.00380.032*
C270.06330 (8)0.31351 (13)0.09442 (9)0.0306 (3)
H270.11040.33060.07930.037*
C280.05700 (7)0.28185 (10)0.16557 (8)0.0242 (2)
H280.09940.27770.19930.029*
C290.01187 (7)0.25637 (10)0.18700 (7)0.0220 (2)
H290.01660.23430.23560.026*
C300.07406 (7)0.26298 (9)0.13763 (6)0.0190 (2)
H300.12090.24490.15280.023*
C310.18532 (6)0.43102 (9)0.02609 (6)0.01644 (18)
C320.16240 (10)0.48334 (11)0.08871 (7)0.0318 (3)
H320.12710.45550.12390.038*
C330.19094 (12)0.57683 (12)0.10029 (8)0.0415 (4)
H330.17500.61240.14340.050*
C340.24236 (10)0.61804 (11)0.04932 (8)0.0303 (3)
H340.26190.68160.05740.036*
C350.26504 (8)0.56624 (10)0.01329 (8)0.0256 (2)
H350.29990.59460.04860.031*
C360.23721 (7)0.47303 (10)0.02494 (7)0.0219 (2)
H360.25360.43760.06790.026*
C370.26260 (6)0.18834 (9)0.18794 (6)0.01470 (17)
C380.21575 (6)0.10661 (9)0.19572 (6)0.0187 (2)
H380.22100.05460.16110.022*
C390.16174 (7)0.10095 (10)0.25368 (7)0.0220 (2)
H390.13120.04430.25930.026*
C400.15213 (7)0.17778 (11)0.30343 (7)0.0226 (2)
H400.11500.17400.34300.027*
C410.19707 (7)0.26011 (10)0.29506 (6)0.0220 (2)
H410.18990.31330.32850.026*
C420.25269 (7)0.26558 (9)0.23798 (6)0.01769 (19)
H420.28370.32180.23320.021*
C430.38650 (6)0.29955 (8)0.12092 (6)0.01403 (17)
C440.38381 (7)0.37536 (9)0.07008 (6)0.01840 (19)
H440.35190.37020.03170.022*
C450.42769 (7)0.45866 (10)0.07527 (7)0.0228 (2)
H450.42520.51050.04080.027*
C460.47497 (7)0.46606 (9)0.13071 (7)0.0220 (2)
H460.50540.52250.13380.026*
C470.47766 (7)0.39092 (9)0.18164 (7)0.0210 (2)
H470.50970.39630.21980.025*
C480.43372 (6)0.30783 (9)0.17714 (6)0.01781 (19)
H480.43580.25670.21220.021*
C490.39554 (6)0.09351 (8)0.13276 (5)0.01357 (17)
C500.45835 (6)0.08074 (9)0.08460 (6)0.01700 (19)
H500.46520.12040.04190.020*
C510.51089 (7)0.01063 (9)0.09859 (7)0.0194 (2)
H510.55400.00370.06610.023*
C520.50052 (7)0.04948 (9)0.16009 (6)0.0187 (2)
H520.53630.09770.16960.022*
C530.43760 (7)0.03841 (9)0.20743 (6)0.0188 (2)
H530.42990.08010.24900.023*
C540.38552 (6)0.03338 (9)0.19448 (6)0.01629 (18)
H540.34310.04140.22780.020*
C550.41587 (7)0.28107 (9)0.10648 (7)0.0206 (2)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ag10.01684 (4)0.01539 (4)0.01166 (3)0.00341 (3)0.00210 (2)0.00063 (2)
S10.02313 (14)0.02779 (15)0.01479 (10)0.00642 (11)0.00123 (10)0.00447 (10)
P10.01547 (12)0.01409 (12)0.01254 (10)0.00292 (9)0.00198 (9)0.00205 (9)
P20.01477 (11)0.01392 (12)0.01151 (10)0.00087 (9)0.00237 (8)0.00050 (8)
P30.01244 (11)0.01482 (12)0.01006 (9)0.00165 (9)0.00071 (8)0.00044 (8)
N10.0219 (5)0.0280 (6)0.0460 (7)0.0024 (4)0.0053 (5)0.0027 (5)
C10.0180 (5)0.0142 (5)0.0136 (4)0.0023 (4)0.0013 (3)0.0014 (3)
C20.0208 (5)0.0169 (5)0.0141 (4)0.0032 (4)0.0009 (4)0.0014 (3)
C30.0208 (5)0.0180 (5)0.0163 (4)0.0035 (4)0.0003 (4)0.0018 (4)
C40.0208 (5)0.0158 (5)0.0191 (4)0.0012 (4)0.0026 (4)0.0021 (4)
C50.0263 (6)0.0173 (5)0.0167 (4)0.0003 (4)0.0031 (4)0.0020 (4)
C60.0229 (5)0.0185 (5)0.0142 (4)0.0008 (4)0.0003 (4)0.0032 (4)
C70.0177 (5)0.0152 (5)0.0141 (4)0.0006 (4)0.0007 (3)0.0023 (3)
C80.0249 (6)0.0308 (7)0.0149 (4)0.0105 (5)0.0021 (4)0.0020 (4)
C90.0312 (7)0.0335 (7)0.0140 (4)0.0079 (5)0.0034 (4)0.0021 (4)
C100.0283 (6)0.0216 (6)0.0161 (4)0.0022 (4)0.0027 (4)0.0029 (4)
C110.0223 (5)0.0263 (6)0.0203 (5)0.0025 (4)0.0051 (4)0.0001 (4)
C120.0187 (5)0.0229 (6)0.0181 (4)0.0040 (4)0.0015 (4)0.0014 (4)
C130.0185 (5)0.0218 (5)0.0142 (4)0.0070 (4)0.0024 (3)0.0032 (4)
C140.0375 (13)0.0239 (11)0.0223 (15)0.0125 (9)0.0104 (13)0.0014 (10)
C150.0478 (15)0.0327 (16)0.0280 (16)0.0222 (13)0.0124 (13)0.0030 (11)
C160.0317 (19)0.052 (2)0.0239 (11)0.0253 (18)0.0106 (14)0.0073 (18)
C170.0235 (12)0.0497 (18)0.0283 (15)0.0089 (11)0.0113 (10)0.0094 (13)
C180.0217 (10)0.0295 (11)0.0236 (14)0.0053 (8)0.0072 (10)0.0073 (11)
C13B0.0185 (5)0.0218 (5)0.0142 (4)0.0070 (4)0.0024 (3)0.0032 (4)
C14B0.036 (3)0.030 (3)0.019 (3)0.002 (2)0.004 (3)0.004 (2)
C15B0.043 (3)0.037 (4)0.026 (3)0.015 (3)0.006 (3)0.004 (3)
C16B0.032 (3)0.039 (4)0.026 (3)0.006 (3)0.014 (2)0.012 (3)
C17B0.029 (3)0.034 (3)0.033 (3)0.005 (2)0.014 (3)0.005 (3)
C18B0.024 (3)0.031 (3)0.026 (3)0.004 (2)0.011 (2)0.007 (3)
C190.0168 (4)0.0174 (5)0.0128 (4)0.0011 (4)0.0029 (3)0.0011 (3)
C200.0227 (5)0.0171 (5)0.0145 (4)0.0016 (4)0.0037 (4)0.0003 (4)
C210.0325 (6)0.0225 (6)0.0144 (4)0.0023 (5)0.0051 (4)0.0018 (4)
C220.0279 (6)0.0272 (6)0.0146 (4)0.0021 (5)0.0063 (4)0.0022 (4)
C230.0305 (6)0.0245 (6)0.0186 (5)0.0049 (5)0.0084 (4)0.0021 (4)
C240.0280 (6)0.0211 (6)0.0168 (4)0.0051 (4)0.0066 (4)0.0010 (4)
C250.0158 (4)0.0164 (5)0.0154 (4)0.0018 (4)0.0021 (3)0.0007 (3)
C260.0181 (5)0.0391 (8)0.0217 (5)0.0022 (5)0.0019 (4)0.0047 (5)
C270.0172 (5)0.0431 (8)0.0311 (6)0.0042 (5)0.0001 (5)0.0022 (6)
C280.0203 (5)0.0246 (6)0.0265 (5)0.0030 (4)0.0050 (4)0.0035 (5)
C290.0234 (5)0.0239 (6)0.0179 (4)0.0045 (4)0.0025 (4)0.0006 (4)
C300.0185 (5)0.0224 (5)0.0162 (4)0.0026 (4)0.0015 (4)0.0018 (4)
C310.0199 (5)0.0154 (5)0.0144 (4)0.0027 (4)0.0041 (3)0.0010 (3)
C320.0530 (9)0.0230 (6)0.0176 (5)0.0137 (6)0.0072 (5)0.0045 (4)
C330.0750 (13)0.0251 (7)0.0223 (6)0.0184 (8)0.0079 (7)0.0087 (5)
C340.0488 (9)0.0186 (6)0.0243 (5)0.0114 (6)0.0072 (6)0.0001 (5)
C350.0294 (6)0.0190 (6)0.0284 (6)0.0071 (5)0.0023 (5)0.0033 (5)
C360.0239 (5)0.0182 (5)0.0230 (5)0.0035 (4)0.0014 (4)0.0003 (4)
C370.0127 (4)0.0187 (5)0.0126 (4)0.0001 (3)0.0002 (3)0.0009 (3)
C380.0170 (5)0.0206 (5)0.0181 (4)0.0027 (4)0.0012 (4)0.0002 (4)
C390.0185 (5)0.0256 (6)0.0213 (5)0.0032 (4)0.0027 (4)0.0047 (4)
C400.0184 (5)0.0320 (7)0.0166 (4)0.0026 (4)0.0037 (4)0.0043 (4)
C410.0227 (5)0.0266 (6)0.0160 (4)0.0042 (4)0.0033 (4)0.0016 (4)
C420.0186 (5)0.0197 (5)0.0145 (4)0.0005 (4)0.0003 (4)0.0014 (4)
C430.0146 (4)0.0138 (4)0.0136 (4)0.0011 (3)0.0002 (3)0.0001 (3)
C440.0196 (5)0.0185 (5)0.0170 (4)0.0025 (4)0.0014 (4)0.0033 (4)
C450.0257 (6)0.0170 (5)0.0250 (5)0.0042 (4)0.0010 (4)0.0038 (4)
C460.0193 (5)0.0170 (5)0.0291 (6)0.0035 (4)0.0024 (4)0.0041 (4)
C470.0189 (5)0.0197 (5)0.0249 (5)0.0017 (4)0.0046 (4)0.0052 (4)
C480.0184 (5)0.0175 (5)0.0181 (4)0.0013 (4)0.0046 (4)0.0004 (4)
C490.0144 (4)0.0143 (4)0.0119 (3)0.0015 (3)0.0007 (3)0.0005 (3)
C500.0161 (4)0.0185 (5)0.0159 (4)0.0017 (4)0.0015 (3)0.0008 (4)
C510.0159 (5)0.0217 (5)0.0201 (4)0.0004 (4)0.0011 (4)0.0021 (4)
C520.0198 (5)0.0161 (5)0.0207 (4)0.0022 (4)0.0047 (4)0.0032 (4)
C530.0228 (5)0.0176 (5)0.0163 (4)0.0012 (4)0.0029 (4)0.0017 (4)
C540.0174 (5)0.0185 (5)0.0127 (4)0.0004 (4)0.0003 (3)0.0008 (3)
C550.0243 (5)0.0131 (5)0.0230 (5)0.0009 (4)0.0070 (4)0.0010 (4)
Geometric parameters (Å, º) top
Ag1—P32.4923 (3)C20—H200.9500
Ag1—P12.5399 (3)C21—C221.3886 (19)
Ag1—S12.6128 (3)C21—H210.9500
Ag1—P22.6863 (3)C22—C231.3900 (19)
S1—C551.6574 (14)C22—H220.9500
P1—C13B1.8216 (12)C23—C241.3884 (16)
P1—C131.8216 (12)C23—H230.9500
P1—C11.8224 (12)C24—H240.9500
P1—C71.8228 (11)C25—C261.3959 (17)
P2—C191.8231 (10)C25—C301.3972 (16)
P2—C311.8293 (12)C26—C271.3922 (19)
P2—C251.8358 (12)C26—H260.9500
P3—C371.8169 (11)C27—C281.386 (2)
P3—C431.8184 (11)C27—H270.9500
P3—C491.8269 (11)C28—C291.3871 (19)
N1—C551.1630 (18)C28—H280.9500
C1—C61.3976 (15)C29—C301.3920 (17)
C1—C21.3989 (15)C29—H290.9500
C2—C31.3888 (17)C30—H300.9500
C2—H20.9500C31—C321.3846 (18)
C3—C41.3913 (17)C31—C361.3950 (17)
C3—H30.9500C32—C331.395 (2)
C4—C51.3883 (17)C32—H320.9500
C4—H40.9500C33—C341.385 (2)
C5—C61.3922 (18)C33—H330.9500
C5—H50.9500C34—C351.380 (2)
C6—H60.9500C34—H340.9500
C7—C121.3924 (16)C35—C361.3870 (18)
C7—C81.3974 (16)C35—H350.9500
C8—C91.3905 (17)C36—H360.9500
C8—H80.9500C37—C421.3956 (16)
C9—C101.3902 (19)C37—C381.4000 (16)
C9—H90.9500C38—C391.3884 (17)
C10—C111.3811 (19)C38—H380.9500
C10—H100.9500C39—C401.3875 (19)
C11—C121.3926 (17)C39—H390.9500
C11—H110.9500C40—C411.3865 (19)
C12—H120.9500C40—H400.9500
C13—C181.384 (4)C41—C421.3960 (16)
C13—C141.396 (4)C41—H410.9500
C14—C151.398 (5)C42—H420.9500
C14—H140.9500C43—C441.3924 (15)
C15—C161.366 (6)C43—C481.3989 (15)
C15—H150.9500C44—C451.3927 (17)
C16—C171.385 (5)C44—H440.9500
C16—H160.9500C45—C461.3875 (19)
C17—C181.390 (4)C45—H450.9500
C17—H170.9500C46—C471.3868 (19)
C18—H180.9500C46—H460.9500
C13B—C14B1.380 (10)C47—C481.3896 (17)
C13B—C18B1.402 (9)C47—H470.9500
C14B—C15B1.397 (12)C48—H480.9500
C14B—H14B0.9500C49—C541.3948 (15)
C15B—C16B1.369 (12)C49—C501.3959 (15)
C15B—H15B0.9500C50—C511.3880 (17)
C16B—C17B1.367 (12)C50—H500.9500
C16B—H16B0.9500C51—C521.3920 (18)
C17B—C18B1.383 (10)C51—H510.9500
C17B—H17B0.9500C52—C531.3861 (17)
C18B—H18B0.9500C52—H520.9500
C19—C201.3913 (16)C53—C541.3936 (16)
C19—C241.4001 (17)C53—H530.9500
C20—C211.3941 (16)C54—H540.9500
P3—Ag1—P1116.740 (10)C21—C20—H20119.8
P3—Ag1—S1117.910 (10)C22—C21—C20120.37 (11)
P1—Ag1—S1102.412 (10)C22—C21—H21119.8
P3—Ag1—P2108.367 (9)C20—C21—H21119.8
P1—Ag1—P2115.139 (10)C21—C22—C23119.56 (11)
S1—Ag1—P294.327 (10)C21—C22—H22120.2
C55—S1—Ag1106.68 (4)C23—C22—H22120.2
C13B—P1—C1102.52 (6)C24—C23—C22120.28 (12)
C13—P1—C1102.52 (6)C24—C23—H23119.9
C13B—P1—C7105.70 (5)C22—C23—H23119.9
C13—P1—C7105.70 (5)C23—C24—C19120.43 (11)
C1—P1—C7103.09 (5)C23—C24—H24119.8
C13B—P1—Ag1109.11 (4)C19—C24—H24119.8
C13—P1—Ag1109.11 (4)C26—C25—C30118.51 (11)
C1—P1—Ag1119.78 (4)C26—C25—P2123.54 (9)
C7—P1—Ag1115.14 (4)C30—C25—P2117.94 (9)
C19—P2—C31100.41 (5)C27—C26—C25120.45 (12)
C19—P2—C25103.84 (5)C27—C26—H26119.8
C31—P2—C25102.54 (5)C25—C26—H26119.8
C19—P2—Ag1109.78 (4)C28—C27—C26120.65 (13)
C31—P2—Ag1111.23 (4)C28—C27—H27119.7
C25—P2—Ag1125.94 (4)C26—C27—H27119.7
C37—P3—C43105.88 (5)C27—C28—C29119.33 (12)
C37—P3—C49102.96 (5)C27—C28—H28120.3
C43—P3—C49101.06 (5)C29—C28—H28120.3
C37—P3—Ag1108.38 (3)C28—C29—C30120.30 (12)
C43—P3—Ag1116.69 (3)C28—C29—H29119.9
C49—P3—Ag1120.25 (3)C30—C29—H29119.9
C6—C1—C2118.94 (11)C29—C30—C25120.76 (11)
C6—C1—P1123.49 (9)C29—C30—H30119.6
C2—C1—P1117.57 (8)C25—C30—H30119.6
C3—C2—C1120.86 (10)C32—C31—C36119.10 (11)
C3—C2—H2119.6C32—C31—P2124.34 (10)
C1—C2—H2119.6C36—C31—P2116.55 (9)
C2—C3—C4119.93 (11)C31—C32—C33120.21 (13)
C2—C3—H3120.0C31—C32—H32119.9
C4—C3—H3120.0C33—C32—H32119.9
C5—C4—C3119.55 (11)C34—C33—C32120.32 (14)
C5—C4—H4120.2C34—C33—H33119.8
C3—C4—H4120.2C32—C33—H33119.8
C4—C5—C6120.81 (11)C35—C34—C33119.58 (13)
C4—C5—H5119.6C35—C34—H34120.2
C6—C5—H5119.6C33—C34—H34120.2
C5—C6—C1119.92 (11)C34—C35—C36120.39 (13)
C5—C6—H6120.0C34—C35—H35119.8
C1—C6—H6120.0C36—C35—H35119.8
C12—C7—C8119.12 (10)C35—C36—C31120.40 (12)
C12—C7—P1122.89 (9)C35—C36—H36119.8
C8—C7—P1117.98 (9)C31—C36—H36119.8
C9—C8—C7120.35 (12)C42—C37—C38119.01 (10)
C9—C8—H8119.8C42—C37—P3123.43 (9)
C7—C8—H8119.8C38—C37—P3117.51 (8)
C10—C9—C8120.07 (12)C39—C38—C37120.56 (11)
C10—C9—H9120.0C39—C38—H38119.7
C8—C9—H9120.0C37—C38—H38119.7
C11—C10—C9119.77 (11)C40—C39—C38120.25 (12)
C11—C10—H10120.1C40—C39—H39119.9
C9—C10—H10120.1C38—C39—H39119.9
C10—C11—C12120.48 (12)C41—C40—C39119.55 (11)
C10—C11—H11119.8C41—C40—H40120.2
C12—C11—H11119.8C39—C40—H40120.2
C7—C12—C11120.19 (11)C40—C41—C42120.67 (12)
C7—C12—H12119.9C40—C41—H41119.7
C11—C12—H12119.9C42—C41—H41119.7
C18—C13—C14119.2 (3)C37—C42—C41119.92 (11)
C18—C13—P1118.50 (19)C37—C42—H42120.0
C14—C13—P1122.1 (2)C41—C42—H42120.0
C13—C14—C15119.7 (4)C44—C43—C48119.38 (10)
C13—C14—H14120.2C44—C43—P3118.88 (8)
C15—C14—H14120.2C48—C43—P3121.69 (8)
C16—C15—C14120.6 (4)C43—C44—C45120.25 (11)
C16—C15—H15119.7C43—C44—H44119.9
C14—C15—H15119.7C45—C44—H44119.9
C15—C16—C17120.1 (4)C46—C45—C44120.13 (12)
C15—C16—H16120.0C46—C45—H45119.9
C17—C16—H16120.0C44—C45—H45119.9
C16—C17—C18120.0 (4)C47—C46—C45119.84 (11)
C16—C17—H17120.0C47—C46—H46120.1
C18—C17—H17120.0C45—C46—H46120.1
C13—C18—C17120.5 (3)C46—C47—C48120.39 (11)
C13—C18—H18119.7C46—C47—H47119.8
C17—C18—H18119.7C48—C47—H47119.8
C14B—C13B—C18B118.0 (6)C47—C48—C43120.00 (11)
C14B—C13B—P1127.7 (5)C47—C48—H48120.0
C18B—C13B—P1114.2 (4)C43—C48—H48120.0
C13B—C14B—C15B119.9 (9)C54—C49—C50119.03 (10)
C13B—C14B—H14B120.1C54—C49—P3124.13 (8)
C15B—C14B—H14B120.1C50—C49—P3116.84 (8)
C16B—C15B—C14B121.1 (11)C51—C50—C49120.58 (10)
C16B—C15B—H15B119.4C51—C50—H50119.7
C14B—C15B—H15B119.4C49—C50—H50119.7
C17B—C16B—C15B119.7 (12)C50—C51—C52120.17 (11)
C17B—C16B—H16B120.2C50—C51—H51119.9
C15B—C16B—H16B120.2C52—C51—H51119.9
C16B—C17B—C18B119.9 (9)C53—C52—C51119.53 (11)
C16B—C17B—H17B120.0C53—C52—H52120.2
C18B—C17B—H17B120.0C51—C52—H52120.2
C17B—C18B—C13B121.3 (8)C52—C53—C54120.48 (11)
C17B—C18B—H18B119.4C52—C53—H53119.8
C13B—C18B—H18B119.4C54—C53—H53119.8
C20—C19—C24119.05 (10)C53—C54—C49120.18 (10)
C20—C19—P2118.61 (9)C53—C54—H54119.9
C24—C19—P2122.33 (9)C49—C54—H54119.9
C19—C20—C21120.31 (11)N1—C55—S1177.60 (13)
C19—C20—H20119.8
C13B—P1—C1—C6103.90 (10)C20—C19—C24—C231.31 (19)
C13—P1—C1—C6103.90 (10)P2—C19—C24—C23179.88 (11)
C7—P1—C1—C65.75 (11)C19—P2—C25—C2612.39 (13)
Ag1—P1—C1—C6135.21 (9)C31—P2—C25—C2691.82 (12)
C13B—P1—C1—C275.74 (10)Ag1—P2—C25—C26139.91 (10)
C13—P1—C1—C275.74 (10)C19—P2—C25—C30168.95 (9)
C7—P1—C1—C2174.62 (9)C31—P2—C25—C3086.84 (10)
Ag1—P1—C1—C245.15 (10)Ag1—P2—C25—C3041.43 (11)
C6—C1—C2—C30.00 (17)C30—C25—C26—C270.9 (2)
P1—C1—C2—C3179.65 (9)P2—C25—C26—C27177.74 (12)
C1—C2—C3—C40.25 (18)C25—C26—C27—C280.1 (2)
C2—C3—C4—C50.27 (18)C26—C27—C28—C290.5 (2)
C3—C4—C5—C60.05 (19)C27—C28—C29—C300.3 (2)
C4—C5—C6—C10.21 (19)C28—C29—C30—C250.5 (2)
C2—C1—C6—C50.23 (18)C26—C25—C30—C291.09 (19)
P1—C1—C6—C5179.86 (9)P2—C25—C30—C29177.64 (10)
C13B—P1—C7—C126.14 (12)C19—P2—C31—C32125.88 (13)
C13—P1—C7—C126.14 (12)C25—P2—C31—C3219.02 (13)
C1—P1—C7—C12101.11 (11)Ag1—P2—C31—C32117.98 (12)
Ag1—P1—C7—C12126.64 (10)C19—P2—C31—C3655.53 (10)
C13B—P1—C7—C8172.97 (10)C25—P2—C31—C36162.39 (9)
C13—P1—C7—C8172.97 (10)Ag1—P2—C31—C3660.61 (10)
C1—P1—C7—C879.78 (11)C36—C31—C32—C330.1 (2)
Ag1—P1—C7—C852.48 (11)P2—C31—C32—C33178.61 (14)
C12—C7—C8—C90.6 (2)C31—C32—C33—C340.0 (3)
P1—C7—C8—C9178.56 (11)C32—C33—C34—C350.3 (3)
C7—C8—C9—C100.6 (2)C33—C34—C35—C360.7 (2)
C8—C9—C10—C111.1 (2)C34—C35—C36—C310.7 (2)
C9—C10—C11—C120.3 (2)C32—C31—C36—C350.4 (2)
C8—C7—C12—C111.33 (19)P2—C31—C36—C35179.11 (10)
P1—C7—C12—C11177.77 (10)C43—P3—C37—C427.22 (11)
C10—C11—C12—C70.9 (2)C49—P3—C37—C42112.89 (10)
C1—P1—C13—C18152.3 (3)Ag1—P3—C37—C42118.70 (9)
C7—P1—C13—C18100.1 (3)C43—P3—C37—C38175.41 (9)
Ag1—P1—C13—C1824.3 (3)C49—P3—C37—C3869.74 (9)
C1—P1—C13—C1422.8 (3)Ag1—P3—C37—C3858.67 (9)
C7—P1—C13—C1484.8 (3)C42—C37—C38—C392.04 (17)
Ag1—P1—C13—C14150.8 (3)P3—C37—C38—C39179.54 (9)
C18—C13—C14—C150.7 (5)C37—C38—C39—C401.93 (19)
P1—C13—C14—C15175.8 (3)C38—C39—C40—C410.29 (19)
C13—C14—C15—C160.5 (7)C39—C40—C41—C421.22 (19)
C14—C15—C16—C171.6 (9)C38—C37—C42—C410.54 (17)
C15—C16—C17—C181.4 (9)P3—C37—C42—C41177.87 (9)
C14—C13—C18—C170.9 (4)C40—C41—C42—C371.09 (18)
P1—C13—C18—C17176.2 (2)C37—P3—C43—C44113.98 (9)
C16—C17—C18—C130.1 (5)C49—P3—C43—C44138.98 (9)
C1—P1—C13B—C14B7.8 (7)Ag1—P3—C43—C446.68 (11)
C7—P1—C13B—C14B99.8 (7)C37—P3—C43—C4868.66 (10)
Ag1—P1—C13B—C14B135.8 (7)C49—P3—C43—C4838.39 (10)
C1—P1—C13B—C18B169.6 (6)Ag1—P3—C43—C48170.68 (8)
C7—P1—C13B—C18B82.8 (6)C48—C43—C44—C450.08 (18)
Ag1—P1—C13B—C18B41.6 (6)P3—C43—C44—C45177.50 (10)
C18B—C13B—C14B—C15B0.3 (11)C43—C44—C45—C460.72 (19)
P1—C13B—C14B—C15B177.0 (7)C44—C45—C46—C470.9 (2)
C13B—C14B—C15B—C16B1.2 (18)C45—C46—C47—C480.5 (2)
C14B—C15B—C16B—C17B2 (3)C46—C47—C48—C430.10 (19)
C15B—C16B—C17B—C18B2 (2)C44—C43—C48—C470.33 (18)
C16B—C17B—C18B—C13B0.8 (16)P3—C43—C48—C47177.02 (9)
C14B—C13B—C18B—C17B0.5 (10)C37—P3—C49—C543.88 (11)
P1—C13B—C18B—C17B177.1 (6)C43—P3—C49—C54113.22 (10)
C31—P2—C19—C20143.05 (10)Ag1—P3—C49—C54116.70 (9)
C25—P2—C19—C20111.13 (10)C37—P3—C49—C50175.99 (8)
Ag1—P2—C19—C2025.83 (10)C43—P3—C49—C5066.66 (9)
C31—P2—C19—C2435.76 (11)Ag1—P3—C49—C5063.42 (9)
C25—P2—C19—C2470.05 (11)C54—C49—C50—C511.30 (17)
Ag1—P2—C19—C24152.98 (9)P3—C49—C50—C51178.58 (9)
C24—C19—C20—C210.92 (18)C49—C50—C51—C521.58 (18)
P2—C19—C20—C21179.77 (10)C50—C51—C52—C530.37 (18)
C19—C20—C21—C220.0 (2)C51—C52—C53—C541.09 (18)
C20—C21—C22—C230.5 (2)C52—C53—C54—C491.36 (17)
C21—C22—C23—C240.1 (2)C50—C49—C54—C530.16 (16)
C22—C23—C24—C190.8 (2)P3—C49—C54—C53179.96 (9)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C3—H3···N1i0.952.633.2987 (19)128
C40—H40···N1ii0.952.683.5540 (18)153
C46—H46···N1iii0.952.523.3460 (18)145
Symmetry codes: (i) x+1, y, z; (ii) x1/2, y+1/2, z1/2; (iii) x+1, y+1, z.
 

Acknowledgements

Financial support from the Department of Chemistry, Faculty of Science, Prince of Songkla University, is gratefully acknowledged. We would like to thank Dr Matthias Zeller and Purdue University for assistance with the X-ray structure determination and use of structure refinement programs funding by The National Science Foundation of United States (CHE-1625543).

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