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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 71| Part 6| June 2015| Pages m133-m134

Crystal structure of bis­­[μ-bis­­(di­phenyl­phosphan­yl)methane-κ2P:P′]-μ-chlorido-chlorido-1κCl-(1-phenyl­thio­urea-2κS)disilver aceto­nitrile hemisolvate

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 T. J. Prior, University of Hull, England (Received 4 May 2015; accepted 9 May 2015; online 23 May 2015)

In the dinuclear title complex, [Ag2Cl2(C7H8N2S)(C25H22P2)2]·0.5CH3CN, each AgI ion displays a distorted tetra­hedral coordination geometry with two P atoms from two bis­(di­phenyl­phosphan­yl)methane (dppm) ligands, one bridging chloride ion, one terminal chloride ion and one terminal S atom from the N,N′-phenyl­thio­urea (ptu) ligand. The dppm ligands and the bridging chloride ion force the two Ag atoms into close proximity, with a short Ag⋯Ag separation of 3.2064 (2) Å. In the crystal, complex mol­ecules are linked by N—H⋯Cl hydrogen bonds forming a dimer. The dimers are linked via weak C— H⋯Cl hydrogen bonds forming a two-dimensional supra­molecular architecture in the yz plane. In addition, an intra­molecular N—H⋯Cl hydrogen bond is observed.

1. Related literature

For the studies of silver(I) complexes containing phosphine and sulfur co-donor ligands, see: Zhang et al. (2003[Zhang, L., Zhang, H.-X., Chen, C.-L., Deng, L.-R. & Kang, B.-S. (2003). Inorg. Chim. Acta, 355, 49-56.]); Wattanakanjana et al. (2013[Wattanakanjana, Y., Pakawatchai, C. & Nimthong, R. (2013). Acta Cryst. E69, m83-m84.]). For their various applications such as anti­microbial activities, 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.]); 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.]).

[Scheme 1]

2. Experimental

2.1. Crystal data

  • [Ag2Cl2(C7H8N2S)(C25H22P2)2]·0.5C2H3N

  • Mr = 2456.22

  • Monoclinic, C 2/c

  • a = 30.6130 (12) Å

  • b = 16.5078 (4) Å

  • c = 21.7975 (6) Å

  • β = 97.129 (2)°

  • V = 10930.3 (6) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 1.01 mm−1

  • T = 100 K

  • 0.38 × 0.27 × 0.05 mm

2.2. Data collection

  • Bruker AXS D8 Quest CMOS diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2014[Bruker (2014). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.564, Tmax = 0.746

  • 43370 measured reflections

  • 13309 independent reflections

  • 11256 reflections with I > 2σ(I)

  • Rint = 0.038

2.3. Refinement

  • R[F2 > 2σ(F2)] = 0.031

  • wR(F2) = 0.076

  • S = 1.09

  • 13309 reflections

  • 628 parameters

  • H-atom parameters constrained

  • Δρmax = 1.11 e Å−3

  • Δρmin = −0.82 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N1—H1⋯Cl2i 0.88 2.32 3.1910 (19) 172
N2—H2A⋯Cl1i 0.88 2.56 3.1618 (19) 126
N2—H2A⋯Cl2i 0.88 2.84 3.595 (2) 144
N2—H2B⋯Cl1 0.88 2.52 3.328 (2) 152
Symmetry code: (i) [-x+{\script{1\over 2}}, -y+{\script{3\over 2}}, -z+1].

Data collection: APEX2 (Bruker, 2014[Bruker (2014). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2014[Bruker (2014). 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, 2015[Sheldrick, G. M. (2015). Acta Cryst. C71, 3-8.]) 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: SHELXL2013.

Supporting information


Experimental top

Bis(di­phenyl­phosphanyl)methane, dppm, (0.1 g, 0.26 mmol) was dissolved in 30 ml of aceto­nitrile at 343 K and then silver(I) chloride, AgCl, (0.04 g, 0.28 mmol) was added. The mixture was stirred for 4 hr and then N,N′-phenyl­thio­urea, ptu, (0.04 g, 0.26 mmol) was added and the new reaction mixture was heated under reflux for 6 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

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); 0.99 Å (CH2) and Uiso(H) = 1.5Ueq(C); 0.88 Å (NH), and Uiso(H) = 1.2Ueq(N).

Results and discussion top

Silver(I) complexes containing phosphine and sulfur co-donor ligands have been studied in recent years (Zhang et al., 2003; Wattanakanjana et al., 2013) because of their various applications such as anti­microbial activities (Isab et al., 2010; Nawaz et al., 2011). Herein, the crystal structure of a dinuclear silver(I) chloride complex containing both dppm and ptu is described.

The title complex is dinuclear in which the AgI ions adopt distorted tetra­hedral geometries. Bis(di­phenyl­phosphanyl)methane (dppm) affords a dinuclear metal complex in the µ-dppm form. There are two kinds of coordination environment around the AgI centres. In one of the Ag centre, the silver atom, Ag1, is tetra­hedrally coordinated to two P atoms of two dppm ligands, one bridging chloride ion and a terminal S atom of N,N'-phenyl­thio­urea (ptu) ligand. In the second centre, the silver atom, Ag2, is bound to two P atoms of two dppm ligands and two chloride ions form the bridging and a terminal Cl atom in a tetra­hedral environment as shown in Fig. 1. The dppm ligands and the bridging chloride ion force the two Ag atoms into close proximity with a short Ag···Ag separation of 3.2064 (2) Å. In the crystal, N1—H1···Cl2i and N2—H2A···Cl1i hydrogen bonds are linked molecules into dimers (Fig. 2 and Table 1). The dimers are connected via a weak C10— H10A···Cl2ii hydrogen bonds [C10(sp3)—H10A···Cl2ii, with H10A···Cl2ii = 2.6379 (6) Å, C10(sp3)···Cl2ii, = 3.581 (2) Å and C10(sp3)—H10A···Cl2ii, = 159.20 (14)°, symmetry code: (ii) 1/2 - x,-1/2 + y, 1/2 - z], leading to the formation of a two-dimensional network parallel to (100), Fig. 3. In addition, an intra­molecular N2—H2B···Cl1 hydrogen bond is observed.

Related literature top

For the studies of silver(I) complexes containing phosphine and sulfur co-donor ligands, see: Zhang et al. (2003); Wattanakanjana et al. (2013). For their various applications such as antimicrobial activities, see: Isab et al. (2010); Nawaz et al. (2011).

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: SHELXL2013 (Sheldrick, 2015) and SHELXLE (Hübschle et al., 2011); molecular graphics: Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL2013 (Sheldrick, 2015).

Figures top
[Figure 1] Fig. 1. The molecular structure with displacement ellipsoids drawn at the 50% probability level. The acetonitrile is omitted for clarity.
[Figure 2] Fig. 2. Part of the crystal structure showing intra-intermolecular N—H···Cl hydrogen bonds forming a dimers as dashed lines.
[Figure 3] Fig. 3. Part of the crystal structure showing intermolecular C—H···Cl hydrogen bonds as dashed lines, forming a two-dimensional network parallel to (100).
Bis[µ-bis(diphenylphosphanyl)methane-κ2P:P']-µ-chlorido-chlorido-1κCl-(1-phenylthiourea-2κS)disilver acetonitrile hemisolvate top
Crystal data top
[Ag2Cl2(C7H8N2S)(C25H22P2)2]·0.5C2H3NF(000) = 4984
Mr = 2456.22Dx = 1.493 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
a = 30.6130 (12) ÅCell parameters from 9809 reflections
b = 16.5078 (4) Åθ = 2.3–28.3°
c = 21.7975 (6) ŵ = 1.01 mm1
β = 97.129 (2)°T = 100 K
V = 10930.3 (6) Å3Plate, colourless
Z = 40.38 × 0.27 × 0.05 mm
Data collection top
Bruker AXS D8 Quest CMOS
diffractometer
13309 independent reflections
Radiation source: I-mu-S microsource X-ray tube11256 reflections with I > 2σ(I)
Laterally graded multilayer (Goebel) mirror monochromatorRint = 0.038
ω and phi scansθmax = 28.3°, θmin = 2.3°
Absorption correction: multi-scan
(SADABS; Bruker, 2014)
h = 4037
Tmin = 0.564, Tmax = 0.746k = 2222
43370 measured reflectionsl = 2927
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)] = 0.031Hydrogen site location: mixed
wR(F2) = 0.076H-atom parameters constrained
S = 1.09 w = 1/[σ2(Fo2) + (0.0258P)2 + 25.3039P]
where P = (Fo2 + 2Fc2)/3
13309 reflections(Δ/σ)max = 0.003
628 parametersΔρmax = 1.11 e Å3
0 restraintsΔρmin = 0.82 e Å3
Crystal data top
[Ag2Cl2(C7H8N2S)(C25H22P2)2]·0.5C2H3NV = 10930.3 (6) Å3
Mr = 2456.22Z = 4
Monoclinic, C2/cMo Kα radiation
a = 30.6130 (12) ŵ = 1.01 mm1
b = 16.5078 (4) ÅT = 100 K
c = 21.7975 (6) Å0.38 × 0.27 × 0.05 mm
β = 97.129 (2)°
Data collection top
Bruker AXS D8 Quest CMOS
diffractometer
13309 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2014)
11256 reflections with I > 2σ(I)
Tmin = 0.564, Tmax = 0.746Rint = 0.038
43370 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0310 restraints
wR(F2) = 0.076H-atom parameters constrained
S = 1.09 w = 1/[σ2(Fo2) + (0.0258P)2 + 25.3039P]
where P = (Fo2 + 2Fc2)/3
13309 reflectionsΔρmax = 1.11 e Å3
628 parametersΔρmin = 0.82 e Å3
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*/UeqOcc. (<1)
Ag10.34726 (2)0.62699 (2)0.43524 (2)0.01319 (4)
Ag20.31458 (2)0.74785 (2)0.32376 (2)0.01379 (5)
Cl10.30072 (2)0.76058 (3)0.44301 (3)0.01595 (11)
Cl20.26067 (2)0.87057 (3)0.29281 (3)0.01781 (11)
S10.37141 (2)0.59639 (4)0.55368 (3)0.01809 (12)
P10.30220 (2)0.52187 (3)0.37837 (3)0.01281 (11)
P20.27329 (2)0.63632 (3)0.27086 (3)0.01257 (11)
P30.42265 (2)0.67660 (3)0.42066 (3)0.01213 (11)
P40.38881 (2)0.80300 (3)0.32099 (3)0.01273 (11)
N10.33087 (6)0.59822 (13)0.65532 (9)0.0194 (4)
H10.30730.60760.67350.023*
N20.29192 (6)0.65224 (13)0.56963 (9)0.0184 (4)
H2A0.27060.66210.59220.022*
H2B0.28880.66570.53030.022*
C10.32886 (7)0.61682 (14)0.59508 (11)0.0147 (4)
C20.36829 (8)0.56437 (16)0.69221 (11)0.0217 (5)
C30.37998 (8)0.48414 (17)0.68583 (12)0.0239 (5)
H30.36360.45070.65580.029*
C40.41607 (9)0.45264 (19)0.72405 (13)0.0291 (6)
H40.42440.39770.71970.035*
C50.43962 (10)0.5012 (2)0.76824 (15)0.0394 (8)
H50.46430.47980.79390.047*
C60.42720 (12)0.5803 (2)0.77492 (17)0.0502 (9)
H60.44300.61330.80580.060*
C70.39154 (11)0.61243 (19)0.73659 (15)0.0384 (7)
H70.38330.66740.74100.046*
C100.29357 (7)0.53409 (13)0.29369 (11)0.0148 (4)
H10A0.27200.49330.27560.018*
H10B0.32170.52420.27690.018*
C110.32532 (7)0.41959 (14)0.39004 (11)0.0171 (5)
C120.34737 (8)0.40255 (16)0.44862 (12)0.0235 (5)
H120.35070.44330.47960.028*
C130.36449 (9)0.32471 (17)0.46129 (14)0.0311 (6)
H130.37950.31280.50110.037*
C140.35973 (9)0.26519 (17)0.41627 (16)0.0340 (7)
H140.37160.21270.42510.041*
C150.33770 (9)0.28230 (17)0.35855 (16)0.0345 (7)
H150.33430.24130.32770.041*
C160.32043 (8)0.35929 (16)0.34516 (14)0.0263 (6)
H160.30530.37060.30530.032*
C200.43242 (7)0.72999 (14)0.34908 (11)0.0152 (4)
H20A0.46080.75920.35670.018*
H20B0.43500.68940.31630.018*
C210.24624 (7)0.50760 (14)0.39803 (11)0.0147 (4)
C220.21789 (8)0.45073 (15)0.36763 (12)0.0227 (5)
H220.22750.41830.33590.027*
C230.17546 (8)0.44093 (16)0.38335 (13)0.0262 (6)
H230.15620.40210.36220.031*
C240.16141 (8)0.48786 (16)0.42986 (12)0.0215 (5)
H240.13260.48070.44090.026*
C250.18909 (8)0.54496 (16)0.46013 (12)0.0234 (5)
H250.17930.57740.49180.028*
C260.23161 (8)0.55497 (15)0.44410 (11)0.0199 (5)
H260.25060.59440.46480.024*
C310.21414 (7)0.63403 (13)0.27840 (11)0.0153 (4)
C320.19907 (7)0.68226 (15)0.32371 (12)0.0197 (5)
H320.21920.71490.34960.024*
C330.15427 (8)0.68285 (16)0.33128 (13)0.0258 (6)
H330.14410.71560.36240.031*
C340.12500 (8)0.63577 (16)0.29355 (13)0.0242 (5)
H340.09470.63600.29880.029*
C350.13970 (8)0.58808 (17)0.24803 (13)0.0261 (6)
H350.11940.55630.22170.031*
C360.18432 (8)0.58659 (16)0.24074 (12)0.0224 (5)
H360.19440.55310.21000.027*
C410.27386 (7)0.63926 (14)0.18740 (11)0.0160 (4)
C420.26697 (8)0.57103 (15)0.14897 (12)0.0204 (5)
H420.26290.51930.16650.024*
C430.26611 (8)0.57888 (17)0.08545 (12)0.0261 (5)
H430.26160.53240.05980.031*
C440.27183 (9)0.65415 (19)0.05911 (12)0.0287 (6)
H440.27130.65910.01560.034*
C450.27831 (9)0.72187 (18)0.09647 (13)0.0285 (6)
H450.28210.77350.07850.034*
C460.27935 (8)0.71476 (15)0.16023 (12)0.0213 (5)
H460.28380.76160.18550.026*
C510.46106 (7)0.59204 (14)0.42004 (11)0.0150 (4)
C520.44499 (7)0.51591 (14)0.43294 (11)0.0179 (5)
H520.41580.51090.44320.021*
C530.47090 (8)0.44711 (15)0.43111 (12)0.0216 (5)
H530.45930.39530.43910.026*
C540.51389 (8)0.45446 (16)0.41752 (12)0.0238 (5)
H540.53190.40770.41690.029*
C550.53054 (8)0.52986 (17)0.40493 (12)0.0242 (5)
H550.56000.53470.39590.029*
C560.50428 (8)0.59852 (16)0.40539 (11)0.0208 (5)
H560.51560.64990.39580.025*
C610.44553 (7)0.74433 (13)0.48286 (10)0.0142 (4)
C620.49017 (8)0.74738 (14)0.50644 (12)0.0200 (5)
H620.51080.71430.48890.024*
C630.50455 (8)0.79865 (16)0.55549 (13)0.0275 (6)
H630.53490.79990.57150.033*
C640.47489 (9)0.84788 (17)0.58114 (13)0.0272 (6)
H640.48490.88300.61450.033*
C650.43043 (9)0.84565 (16)0.55794 (12)0.0245 (5)
H650.41010.87970.57520.029*
C660.41579 (8)0.79381 (15)0.50974 (11)0.0193 (5)
H660.38530.79170.49470.023*
C710.40652 (7)0.82620 (14)0.24539 (11)0.0162 (4)
C720.39431 (8)0.77072 (16)0.19800 (12)0.0214 (5)
H720.37590.72630.20510.026*
C730.40891 (9)0.77995 (18)0.14049 (13)0.0275 (6)
H730.40090.74130.10880.033*
C740.43512 (8)0.84561 (18)0.12935 (12)0.0275 (6)
H740.44520.85190.09010.033*
C750.44653 (8)0.90190 (18)0.17565 (13)0.0271 (6)
H750.46400.94740.16780.033*
C760.43253 (8)0.89235 (15)0.23358 (12)0.0207 (5)
H760.44070.93100.26520.025*
C810.40104 (7)0.89352 (14)0.36760 (11)0.0159 (4)
C820.36545 (8)0.94055 (14)0.38123 (11)0.0185 (5)
H820.33630.92500.36570.022*
C830.37246 (9)1.00972 (16)0.41718 (12)0.0252 (5)
H830.34821.04190.42570.030*
C840.41509 (9)1.03167 (16)0.44066 (13)0.0274 (6)
H840.41991.07880.46560.033*
C850.45069 (9)0.98535 (17)0.42795 (13)0.0274 (6)
H850.47971.00070.44420.033*
C860.44392 (8)0.91653 (15)0.39146 (12)0.0209 (5)
H860.46830.88500.38260.025*
N30.50000.0799 (3)0.25000.0509 (11)
C80.50000.1474 (3)0.25000.0472 (12)
C90.50000.2356 (4)0.25000.114 (3)
H9A0.51940.25500.22190.171*0.5
H9B0.47070.25500.23720.171*0.5
H9C0.50990.25500.29090.171*0.5
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ag10.01265 (8)0.01232 (8)0.01462 (9)0.00062 (6)0.00176 (6)0.00100 (6)
Ag20.01315 (8)0.01121 (8)0.01675 (9)0.00039 (6)0.00076 (6)0.00092 (6)
Cl10.0165 (2)0.0153 (3)0.0160 (3)0.00499 (19)0.00185 (19)0.0005 (2)
Cl20.0170 (2)0.0160 (3)0.0208 (3)0.00423 (19)0.0038 (2)0.0054 (2)
S10.0151 (2)0.0261 (3)0.0135 (3)0.0066 (2)0.0036 (2)0.0031 (2)
P10.0133 (2)0.0107 (3)0.0145 (3)0.00021 (19)0.0021 (2)0.0001 (2)
P20.0136 (2)0.0111 (3)0.0129 (3)0.00047 (19)0.0012 (2)0.0005 (2)
P30.0117 (2)0.0126 (3)0.0122 (3)0.00089 (19)0.0016 (2)0.0008 (2)
P40.0129 (2)0.0123 (3)0.0129 (3)0.0004 (2)0.0013 (2)0.0006 (2)
N10.0171 (9)0.0257 (11)0.0163 (11)0.0029 (8)0.0056 (8)0.0006 (8)
N20.0147 (9)0.0251 (11)0.0149 (10)0.0049 (8)0.0003 (7)0.0039 (8)
C10.0139 (10)0.0151 (11)0.0153 (12)0.0016 (8)0.0030 (8)0.0034 (9)
C20.0212 (11)0.0290 (14)0.0160 (12)0.0015 (10)0.0060 (9)0.0058 (10)
C30.0201 (11)0.0350 (15)0.0178 (13)0.0031 (10)0.0067 (9)0.0040 (11)
C40.0264 (13)0.0379 (16)0.0246 (15)0.0067 (11)0.0093 (11)0.0134 (12)
C50.0336 (15)0.052 (2)0.0297 (17)0.0015 (14)0.0076 (12)0.0210 (14)
C60.064 (2)0.043 (2)0.036 (2)0.0120 (17)0.0238 (16)0.0102 (15)
C70.0529 (18)0.0304 (16)0.0282 (17)0.0040 (13)0.0099 (13)0.0099 (13)
C100.0164 (10)0.0123 (10)0.0163 (12)0.0002 (8)0.0044 (8)0.0011 (8)
C110.0149 (10)0.0137 (11)0.0229 (13)0.0004 (8)0.0032 (9)0.0018 (9)
C120.0296 (13)0.0195 (12)0.0216 (14)0.0000 (10)0.0043 (10)0.0020 (10)
C130.0351 (14)0.0257 (14)0.0316 (16)0.0057 (11)0.0002 (12)0.0109 (12)
C140.0328 (14)0.0162 (13)0.051 (2)0.0078 (11)0.0003 (13)0.0064 (12)
C150.0342 (14)0.0180 (13)0.049 (2)0.0058 (11)0.0034 (13)0.0067 (13)
C160.0253 (12)0.0185 (13)0.0326 (16)0.0055 (10)0.0061 (11)0.0046 (11)
C200.0132 (10)0.0164 (11)0.0166 (12)0.0016 (8)0.0041 (8)0.0039 (9)
C210.0163 (10)0.0137 (11)0.0143 (11)0.0004 (8)0.0029 (8)0.0019 (9)
C220.0216 (11)0.0223 (13)0.0258 (14)0.0041 (9)0.0088 (10)0.0110 (10)
C230.0209 (12)0.0262 (14)0.0323 (15)0.0090 (10)0.0064 (10)0.0095 (11)
C240.0166 (11)0.0256 (13)0.0232 (13)0.0015 (9)0.0062 (9)0.0005 (10)
C250.0248 (12)0.0246 (13)0.0229 (13)0.0020 (10)0.0110 (10)0.0059 (10)
C260.0217 (11)0.0197 (12)0.0188 (13)0.0060 (9)0.0046 (9)0.0048 (9)
C310.0163 (10)0.0114 (10)0.0181 (12)0.0012 (8)0.0020 (8)0.0033 (9)
C320.0180 (11)0.0188 (12)0.0227 (13)0.0022 (9)0.0038 (9)0.0027 (10)
C330.0236 (12)0.0262 (14)0.0298 (15)0.0012 (10)0.0114 (11)0.0055 (11)
C340.0169 (11)0.0251 (13)0.0315 (15)0.0006 (9)0.0064 (10)0.0031 (11)
C350.0205 (12)0.0279 (14)0.0295 (15)0.0051 (10)0.0021 (10)0.0039 (11)
C360.0174 (11)0.0242 (13)0.0256 (14)0.0027 (9)0.0028 (9)0.0074 (10)
C410.0137 (10)0.0172 (11)0.0172 (12)0.0015 (8)0.0024 (8)0.0015 (9)
C420.0222 (11)0.0197 (12)0.0194 (13)0.0019 (9)0.0037 (9)0.0020 (10)
C430.0282 (13)0.0307 (14)0.0187 (13)0.0011 (11)0.0004 (10)0.0051 (11)
C440.0314 (13)0.0416 (17)0.0129 (13)0.0030 (12)0.0024 (10)0.0025 (11)
C450.0357 (14)0.0289 (14)0.0207 (14)0.0009 (11)0.0030 (11)0.0080 (11)
C460.0249 (12)0.0187 (12)0.0202 (13)0.0017 (9)0.0021 (10)0.0021 (10)
C510.0138 (10)0.0183 (11)0.0127 (11)0.0057 (8)0.0006 (8)0.0001 (9)
C520.0185 (10)0.0172 (11)0.0178 (12)0.0034 (9)0.0023 (9)0.0006 (9)
C530.0268 (12)0.0168 (12)0.0202 (13)0.0054 (9)0.0008 (10)0.0008 (9)
C540.0242 (12)0.0278 (14)0.0184 (13)0.0140 (10)0.0010 (10)0.0030 (10)
C550.0176 (11)0.0378 (15)0.0174 (13)0.0099 (10)0.0031 (9)0.0018 (11)
C560.0193 (11)0.0271 (13)0.0161 (12)0.0025 (9)0.0031 (9)0.0050 (10)
C610.0161 (10)0.0145 (11)0.0118 (11)0.0022 (8)0.0015 (8)0.0015 (8)
C620.0175 (11)0.0170 (12)0.0245 (13)0.0013 (9)0.0014 (9)0.0023 (10)
C630.0224 (12)0.0257 (14)0.0318 (16)0.0061 (10)0.0066 (10)0.0001 (11)
C640.0350 (14)0.0246 (13)0.0206 (14)0.0127 (11)0.0019 (11)0.0042 (11)
C650.0300 (13)0.0234 (13)0.0209 (13)0.0047 (10)0.0067 (10)0.0033 (10)
C660.0173 (10)0.0222 (12)0.0185 (12)0.0026 (9)0.0028 (9)0.0001 (10)
C710.0153 (10)0.0162 (11)0.0171 (12)0.0033 (8)0.0021 (8)0.0040 (9)
C720.0227 (11)0.0227 (12)0.0181 (13)0.0001 (9)0.0001 (9)0.0011 (10)
C730.0270 (13)0.0358 (15)0.0193 (14)0.0069 (11)0.0012 (10)0.0039 (11)
C740.0199 (12)0.0449 (17)0.0190 (13)0.0063 (11)0.0072 (10)0.0066 (12)
C750.0224 (12)0.0342 (15)0.0261 (15)0.0003 (10)0.0082 (10)0.0078 (11)
C760.0200 (11)0.0205 (12)0.0217 (13)0.0018 (9)0.0029 (9)0.0040 (10)
C810.0200 (10)0.0149 (11)0.0129 (11)0.0014 (8)0.0027 (8)0.0011 (9)
C820.0207 (11)0.0169 (11)0.0183 (12)0.0042 (9)0.0038 (9)0.0007 (9)
C830.0333 (13)0.0189 (12)0.0247 (14)0.0007 (10)0.0093 (11)0.0020 (10)
C840.0428 (15)0.0181 (12)0.0214 (14)0.0099 (11)0.0040 (11)0.0061 (10)
C850.0324 (13)0.0255 (14)0.0228 (14)0.0134 (11)0.0028 (11)0.0016 (11)
C860.0189 (11)0.0199 (12)0.0238 (13)0.0047 (9)0.0021 (9)0.0025 (10)
N30.051 (2)0.047 (3)0.051 (3)0.0000.010 (2)0.000
C80.042 (3)0.052 (3)0.043 (3)0.0000.011 (2)0.000
C90.165 (9)0.043 (4)0.120 (8)0.0000.036 (6)0.000
Geometric parameters (Å, º) top
Ag1—P12.4548 (6)C32—H320.9500
Ag1—P32.5060 (6)C33—C341.379 (4)
Ag1—Cl12.6422 (5)C33—H330.9500
Ag1—S12.6445 (6)C34—C351.385 (4)
Ag1—Ag23.2064 (2)C34—H340.9500
Ag2—P22.4403 (6)C35—C361.395 (3)
Ag2—P42.4555 (6)C35—H350.9500
Ag2—Cl22.6470 (6)C36—H360.9500
Ag2—Cl12.6933 (6)C41—C461.399 (3)
S1—C11.708 (2)C41—C421.404 (3)
P1—C211.832 (2)C42—C431.388 (4)
P1—C111.836 (2)C42—H420.9500
P1—C101.843 (2)C43—C441.389 (4)
P2—C411.822 (2)C43—H430.9500
P2—C311.839 (2)C44—C451.383 (4)
P2—C101.845 (2)C44—H440.9500
P3—C511.826 (2)C45—C461.391 (4)
P3—C611.828 (2)C45—H450.9500
P3—C201.848 (2)C46—H460.9500
P4—C811.820 (2)C51—C521.391 (3)
P4—C711.838 (2)C51—C561.403 (3)
P4—C201.846 (2)C52—C531.389 (3)
N1—C11.342 (3)C52—H520.9500
N1—C21.429 (3)C53—C541.390 (3)
N1—H10.8800C53—H530.9500
N2—C11.331 (3)C54—C551.385 (4)
N2—H2A0.8800C54—H540.9500
N2—H2B0.8800C55—C561.390 (3)
C2—C71.379 (4)C55—H550.9500
C2—C31.383 (4)C56—H560.9500
C3—C41.399 (4)C61—C621.400 (3)
C3—H30.9500C61—C661.404 (3)
C4—C51.385 (5)C62—C631.392 (4)
C4—H40.9500C62—H620.9500
C5—C61.372 (5)C63—C641.387 (4)
C5—H50.9500C63—H630.9500
C6—C71.395 (4)C64—C651.392 (4)
C6—H60.9500C64—H640.9500
C7—H70.9500C65—C661.386 (4)
C10—H10A0.9900C65—H650.9500
C10—H10B0.9900C66—H660.9500
C11—C161.391 (4)C71—C761.394 (3)
C11—C121.397 (4)C71—C721.396 (3)
C12—C131.402 (4)C72—C731.390 (4)
C12—H120.9500C72—H720.9500
C13—C141.383 (4)C73—C741.388 (4)
C13—H130.9500C73—H730.9500
C14—C151.381 (4)C74—C751.384 (4)
C14—H140.9500C74—H740.9500
C15—C161.393 (4)C75—C761.392 (3)
C15—H150.9500C75—H750.9500
C16—H160.9500C76—H760.9500
C20—H20A0.9900C81—C821.399 (3)
C20—H20B0.9900C81—C861.403 (3)
C21—C221.390 (3)C82—C831.386 (3)
C21—C261.390 (3)C82—H820.9500
C22—C231.393 (3)C83—C841.390 (4)
C22—H220.9500C83—H830.9500
C23—C241.386 (3)C84—C851.387 (4)
C23—H230.9500C84—H840.9500
C24—C251.380 (4)C85—C861.387 (4)
C24—H240.9500C85—H850.9500
C25—C261.399 (3)C86—H860.9500
C25—H250.9500N3—C81.113 (7)
C26—H260.9500C8—C91.456 (9)
C31—C361.391 (3)C9—H9A0.9600
C31—C321.391 (3)C9—H9B0.9600
C32—C331.402 (3)C9—H9C0.9600
P1—Ag1—P3129.466 (19)C21—C26—C25120.5 (2)
P1—Ag1—Cl1110.406 (19)C21—C26—H26119.8
P3—Ag1—Cl1104.346 (18)C25—C26—H26119.8
P1—Ag1—S1115.43 (2)C36—C31—C32119.3 (2)
P3—Ag1—S192.061 (19)C36—C31—P2122.72 (17)
Cl1—Ag1—S1100.632 (18)C32—C31—P2117.95 (18)
P1—Ag1—Ag287.379 (15)C31—C32—C33120.2 (2)
P3—Ag1—Ag284.618 (14)C31—C32—H32119.9
Cl1—Ag1—Ag253.794 (13)C33—C32—H32119.9
S1—Ag1—Ag2151.860 (15)C34—C33—C32119.9 (2)
P2—Ag2—P4134.00 (2)C34—C33—H33120.0
P2—Ag2—Cl2100.775 (19)C32—C33—H33120.0
P4—Ag2—Cl2105.042 (19)C33—C34—C35120.2 (2)
P2—Ag2—Cl1112.368 (19)C33—C34—H34119.9
P4—Ag2—Cl1104.589 (19)C35—C34—H34119.9
Cl2—Ag2—Cl191.050 (17)C34—C35—C36120.1 (2)
P2—Ag2—Ag189.045 (15)C34—C35—H35119.9
P4—Ag2—Ag192.677 (15)C36—C35—H35119.9
Cl2—Ag2—Ag1142.687 (14)C31—C36—C35120.2 (2)
Cl1—Ag2—Ag152.334 (12)C31—C36—H36119.9
Ag1—Cl1—Ag273.872 (14)C35—C36—H36119.9
C1—S1—Ag1109.82 (8)C46—C41—C42118.6 (2)
C21—P1—C11101.82 (10)C46—C41—P2117.58 (18)
C21—P1—C10103.09 (10)C42—C41—P2123.71 (18)
C11—P1—C10104.14 (11)C43—C42—C41120.2 (2)
C21—P1—Ag1117.13 (8)C43—C42—H42119.9
C11—P1—Ag1113.41 (8)C41—C42—H42119.9
C10—P1—Ag1115.47 (7)C42—C43—C44120.5 (3)
C41—P2—C31102.79 (10)C42—C43—H43119.7
C41—P2—C10104.42 (10)C44—C43—H43119.7
C31—P2—C10105.02 (10)C45—C44—C43119.7 (2)
C41—P2—Ag2112.53 (7)C45—C44—H44120.1
C31—P2—Ag2115.55 (8)C43—C44—H44120.1
C10—P2—Ag2115.17 (8)C44—C45—C46120.3 (3)
C51—P3—C61106.56 (10)C44—C45—H45119.9
C51—P3—C20100.74 (10)C46—C45—H45119.9
C61—P3—C20104.31 (10)C45—C46—C41120.6 (2)
C51—P3—Ag1110.80 (8)C45—C46—H46119.7
C61—P3—Ag1112.33 (7)C41—C46—H46119.7
C20—P3—Ag1120.72 (7)C52—C51—C56118.8 (2)
C81—P4—C71105.44 (11)C52—C51—P3116.41 (16)
C81—P4—C20105.12 (11)C56—C51—P3124.72 (19)
C71—P4—C2098.72 (10)C53—C52—C51121.0 (2)
C81—P4—Ag2114.69 (7)C53—C52—H52119.5
C71—P4—Ag2118.44 (8)C51—C52—H52119.5
C20—P4—Ag2112.53 (7)C52—C53—C54119.6 (2)
C1—N1—C2125.16 (19)C52—C53—H53120.2
C1—N1—H1117.4C54—C53—H53120.2
C2—N1—H1117.4C55—C54—C53120.1 (2)
C1—N2—H2A120.0C55—C54—H54119.9
C1—N2—H2B120.0C53—C54—H54119.9
H2A—N2—H2B120.0C54—C55—C56120.2 (2)
N2—C1—N1116.19 (19)C54—C55—H55119.9
N2—C1—S1122.04 (18)C56—C55—H55119.9
N1—C1—S1121.77 (17)C55—C56—C51120.1 (2)
C7—C2—C3120.3 (3)C55—C56—H56119.9
C7—C2—N1118.5 (2)C51—C56—H56119.9
C3—C2—N1121.1 (2)C62—C61—C66118.7 (2)
C2—C3—C4119.4 (3)C62—C61—P3124.12 (18)
C2—C3—H3120.3C66—C61—P3117.16 (17)
C4—C3—H3120.3C63—C62—C61120.4 (2)
C5—C4—C3120.2 (3)C63—C62—H62119.8
C5—C4—H4119.9C61—C62—H62119.8
C3—C4—H4119.9C64—C63—C62120.4 (2)
C6—C5—C4119.8 (3)C64—C63—H63119.8
C6—C5—H5120.1C62—C63—H63119.8
C4—C5—H5120.1C63—C64—C65119.8 (2)
C5—C6—C7120.3 (3)C63—C64—H64120.1
C5—C6—H6119.8C65—C64—H64120.1
C7—C6—H6119.8C66—C65—C64120.1 (2)
C2—C7—C6119.9 (3)C66—C65—H65120.0
C2—C7—H7120.0C64—C65—H65120.0
C6—C7—H7120.0C65—C66—C61120.7 (2)
P1—C10—P2111.83 (11)C65—C66—H66119.7
P1—C10—H10A109.3C61—C66—H66119.7
P2—C10—H10A109.3C76—C71—C72118.9 (2)
P1—C10—H10B109.3C76—C71—P4124.59 (19)
P2—C10—H10B109.3C72—C71—P4116.42 (18)
H10A—C10—H10B107.9C73—C72—C71120.6 (2)
C16—C11—C12119.8 (2)C73—C72—H72119.7
C16—C11—P1123.70 (19)C71—C72—H72119.7
C12—C11—P1116.48 (18)C74—C73—C72120.1 (3)
C11—C12—C13119.4 (3)C74—C73—H73120.0
C11—C12—H12120.3C72—C73—H73120.0
C13—C12—H12120.3C75—C74—C73119.7 (2)
C14—C13—C12120.5 (3)C75—C74—H74120.1
C14—C13—H13119.8C73—C74—H74120.1
C12—C13—H13119.8C74—C75—C76120.5 (2)
C15—C14—C13119.8 (3)C74—C75—H75119.8
C15—C14—H14120.1C76—C75—H75119.8
C13—C14—H14120.1C75—C76—C71120.2 (2)
C14—C15—C16120.5 (3)C75—C76—H76119.9
C14—C15—H15119.8C71—C76—H76119.9
C16—C15—H15119.8C82—C81—C86119.2 (2)
C11—C16—C15120.1 (3)C82—C81—P4117.55 (17)
C11—C16—H16120.0C86—C81—P4123.20 (18)
C15—C16—H16120.0C83—C82—C81120.5 (2)
P4—C20—P3113.90 (11)C83—C82—H82119.8
P4—C20—H20A108.8C81—C82—H82119.8
P3—C20—H20A108.8C82—C83—C84119.7 (2)
P4—C20—H20B108.8C82—C83—H83120.2
P3—C20—H20B108.8C84—C83—H83120.2
H20A—C20—H20B107.7C85—C84—C83120.5 (2)
C22—C21—C26119.1 (2)C85—C84—H84119.7
C22—C21—P1121.47 (17)C83—C84—H84119.7
C26—C21—P1119.42 (17)C84—C85—C86120.0 (2)
C21—C22—C23120.5 (2)C84—C85—H85120.0
C21—C22—H22119.8C86—C85—H85120.0
C23—C22—H22119.8C85—C86—C81120.0 (2)
C24—C23—C22119.9 (2)C85—C86—H86120.0
C24—C23—H23120.1C81—C86—H86120.0
C22—C23—H23120.1N3—C8—C9180.0
C25—C24—C23120.2 (2)C8—C9—H9A109.5
C25—C24—H24119.9C8—C9—H9B109.5
C23—C24—H24119.9H9A—C9—H9B109.5
C24—C25—C26119.8 (2)C8—C9—H9C109.5
C24—C25—H25120.1H9A—C9—H9C109.5
C26—C25—H25120.1H9B—C9—H9C109.5
C2—N1—C1—N2176.2 (2)C10—P2—C41—C46152.26 (18)
C2—N1—C1—S13.6 (3)Ag2—P2—C41—C4626.7 (2)
Ag1—S1—C1—N27.5 (2)C31—P2—C41—C4278.4 (2)
Ag1—S1—C1—N1172.72 (17)C10—P2—C41—C4231.0 (2)
C1—N1—C2—C7109.2 (3)Ag2—P2—C41—C42156.62 (17)
C1—N1—C2—C373.7 (3)C46—C41—C42—C430.6 (3)
C7—C2—C3—C41.1 (4)P2—C41—C42—C43177.34 (18)
N1—C2—C3—C4178.1 (2)C41—C42—C43—C440.3 (4)
C2—C3—C4—C50.6 (4)C42—C43—C44—C450.2 (4)
C3—C4—C5—C60.6 (4)C43—C44—C45—C460.3 (4)
C4—C5—C6—C71.3 (5)C44—C45—C46—C410.0 (4)
C3—C2—C7—C60.5 (4)C42—C41—C46—C450.5 (4)
N1—C2—C7—C6177.6 (3)P2—C41—C46—C45177.4 (2)
C5—C6—C7—C20.8 (5)C61—P3—C51—C52116.89 (19)
C21—P1—C10—P277.44 (13)C20—P3—C51—C52134.51 (19)
C11—P1—C10—P2176.57 (11)Ag1—P3—C51—C525.6 (2)
Ag1—P1—C10—P251.55 (13)C61—P3—C51—C5665.6 (2)
C41—P2—C10—P1172.99 (11)C20—P3—C51—C5643.0 (2)
C31—P2—C10—P179.21 (14)Ag1—P3—C51—C56171.93 (19)
Ag2—P2—C10—P149.07 (12)C56—C51—C52—C530.4 (4)
C21—P1—C11—C1685.6 (2)P3—C51—C52—C53177.28 (19)
C10—P1—C11—C1621.4 (2)C51—C52—C53—C541.4 (4)
Ag1—P1—C11—C16147.70 (19)C52—C53—C54—C551.0 (4)
C21—P1—C11—C1291.87 (19)C53—C54—C55—C560.4 (4)
C10—P1—C11—C12161.19 (18)C54—C55—C56—C511.5 (4)
Ag1—P1—C11—C1234.9 (2)C52—C51—C56—C551.1 (4)
C16—C11—C12—C130.3 (4)P3—C51—C56—C55178.53 (19)
P1—C11—C12—C13177.82 (19)C51—P3—C61—C6223.1 (2)
C11—C12—C13—C140.1 (4)C20—P3—C61—C6282.9 (2)
C12—C13—C14—C150.4 (4)Ag1—P3—C61—C62144.64 (18)
C13—C14—C15—C160.4 (5)C51—P3—C61—C66154.37 (18)
C12—C11—C16—C150.4 (4)C20—P3—C61—C6699.57 (19)
P1—C11—C16—C15177.7 (2)Ag1—P3—C61—C6632.9 (2)
C14—C15—C16—C110.0 (4)C66—C61—C62—C630.1 (4)
C81—P4—C20—P380.76 (14)P3—C61—C62—C63177.56 (19)
C71—P4—C20—P3170.55 (13)C61—C62—C63—C640.6 (4)
Ag2—P4—C20—P344.73 (14)C62—C63—C64—C650.4 (4)
C51—P3—C20—P4163.44 (13)C63—C64—C65—C660.6 (4)
C61—P3—C20—P486.20 (14)C64—C65—C66—C611.4 (4)
Ag1—P3—C20—P441.22 (16)C62—C61—C66—C651.1 (3)
C11—P1—C21—C2257.0 (2)P3—C61—C66—C65178.75 (19)
C10—P1—C21—C2250.8 (2)C81—P4—C71—C7612.8 (2)
Ag1—P1—C21—C22178.74 (18)C20—P4—C71—C7695.7 (2)
C11—P1—C21—C26123.4 (2)Ag2—P4—C71—C76142.73 (18)
C10—P1—C21—C26128.8 (2)C81—P4—C71—C72170.29 (18)
Ag1—P1—C21—C260.8 (2)C20—P4—C71—C7281.27 (19)
C26—C21—C22—C230.4 (4)Ag2—P4—C71—C7240.3 (2)
P1—C21—C22—C23180.0 (2)C76—C71—C72—C731.9 (4)
C21—C22—C23—C240.4 (4)P4—C71—C72—C73175.26 (19)
C22—C23—C24—C250.8 (4)C71—C72—C73—C741.3 (4)
C23—C24—C25—C260.5 (4)C72—C73—C74—C750.2 (4)
C22—C21—C26—C250.7 (4)C73—C74—C75—C761.1 (4)
P1—C21—C26—C25179.7 (2)C74—C75—C76—C710.5 (4)
C24—C25—C26—C210.2 (4)C72—C71—C76—C750.9 (4)
C41—P2—C31—C3642.3 (2)P4—C71—C76—C75175.93 (19)
C10—P2—C31—C3666.7 (2)C71—P4—C81—C82108.82 (19)
Ag2—P2—C31—C36165.25 (18)C20—P4—C81—C82147.44 (18)
C41—P2—C31—C32137.48 (19)Ag2—P4—C81—C8223.3 (2)
C10—P2—C31—C32113.5 (2)C71—P4—C81—C8673.0 (2)
Ag2—P2—C31—C3214.5 (2)C20—P4—C81—C8630.8 (2)
C36—C31—C32—C330.1 (4)Ag2—P4—C81—C86154.91 (18)
P2—C31—C32—C33179.9 (2)C86—C81—C82—C830.9 (4)
C31—C32—C33—C340.3 (4)P4—C81—C82—C83179.17 (19)
C32—C33—C34—C350.2 (4)C81—C82—C83—C841.1 (4)
C33—C34—C35—C360.9 (4)C82—C83—C84—C850.6 (4)
C32—C31—C36—C350.6 (4)C83—C84—C85—C860.1 (4)
P2—C31—C36—C35179.2 (2)C84—C85—C86—C810.3 (4)
C34—C35—C36—C311.1 (4)C82—C81—C86—C850.2 (4)
C31—P2—C41—C4698.31 (19)P4—C81—C86—C85178.40 (19)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···Cl2i0.882.323.1910 (19)172
N2—H2A···Cl1i0.882.563.1618 (19)126
N2—H2A···Cl2i0.882.843.595 (2)144
N2—H2B···Cl10.882.523.328 (2)152
Symmetry code: (i) x+1/2, y+3/2, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···Cl2i0.882.323.1910 (19)171.5
N2—H2A···Cl1i0.882.563.1618 (19)126.1
N2—H2A···Cl2i0.882.843.595 (2)144.2
N2—H2B···Cl10.882.523.328 (2)152.1
Symmetry code: (i) x+1/2, y+3/2, z+1.
 

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 71| Part 6| June 2015| Pages m133-m134
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