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

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ISSN: 2056-9890

Bis[μ-bis­­(di­phenyl­phosphino)methane-κ2P:P′]bis­­[(chloro­di­fluoro­acetato-κO)silver(I)](AgAg)

aDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
*Correspondence e-mail: seikweng@um.edu.my

(Received 27 March 2008; accepted 20 April 2008; online 26 April 2008)

The asymmetric unit of the title compound, [Ag2(C2ClF2O2)2(C25H22P2)2], consists of two half-mol­ecules, each AgI ion lying on a center of symmetry. In each complete mol­ecule, two bis­(diphenyl­phosphino)methane ligands bridge two AgI ions, which are further coordinated by one chloro­difluoro­acetate ligand, giving T-shaped geometries and short intra­molecular Ag⋯Ag distances of 3.1078 (6) and 2.9950 (6) Å. In one mol­ecule, the unique –CF2Cl group is rotationally disordered over two sites with approximate occupancies of 0.53 and 0.47 for the major and minor components, respectively.

Related literature

The compound is isostructural with [Ag(O2CCF3)(C6H5)2PCH2P(C6H5)2]2, see: Effendy et al. (2005[Effendy, Di Nocola, C., Nitiatmodjo, M., Pettinari, C., Skelton, B. W. & White, A. H. (2005). Inorg. Chim. Acta, 358, 735-747.]). The report also provides background literature on complexes of bis­(di­phenyl­phosphino)methane with univalent coinage metals.

[Scheme 1]

Experimental

Crystal data
  • [Ag2(C2ClF2O2)2(C25H22P2)2]

  • Mr = 1243.41

  • Triclinic, [P \overline 1]

  • a = 10.8127 (3) Å

  • b = 14.4911 (3) Å

  • c = 17.2340 (3) Å

  • α = 83.040 (1)°

  • β = 86.477 (1)°

  • γ = 72.188 (1)°

  • V = 2551.1 (1) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 1.06 mm−1

  • T = 100 (2) K

  • 0.30 × 0.20 × 0.15 mm

Data collection
  • Bruker SMART APEXdiffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.648, Tmax = 0.857

  • 31942 measured reflections

  • 11567 independent reflections

  • 8338 reflections with I > 2σ(I)

  • Rint = 0.066

Refinement
  • R[F2 > 2σ(F2)] = 0.045

  • wR(F2) = 0.112

  • S = 1.01

  • 11567 reflections

  • 641 parameters

  • 54 restraints

  • H-atom parameters constrained

  • Δρmax = 0.91 e Å−3

  • Δρmin = −1.05 e Å−3

Table 1
Selected geometric parameters (Å, °)

Ag1—O1 2.382 (3)
Ag1—P1 2.4194 (12)
Ag1—P2i 2.419 (1)
Ag2—O3 2.383 (3)
Ag2—P3 2.430 (1)
Ag2—P4ii 2.429 (1)
O1—Ag1—P1 100.92 (9)
O1—Ag1—P2i 103.78 (9)
P1—Ag1—P2i 151.19 (4)
O3—Ag2—P3 104.14 (8)
O3—Ag2—P4ii 101.43 (8)
P3—Ag2—P4ii 149.67 (4)
Symmetry codes: (i) -x+1, -y+2, -z+2; (ii) -x+1, -y+1, -z+1.

Data collection: APEX2 (Bruker, 2007[Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). APEX2 and SAINT. 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: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: X-SEED (Barbour, 2001[Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-191.]); software used to prepare material for publication: publCIF (Westrip, 2008[Westrip, S. P. (2008). publCIF. In preparation.]).

Supporting information


Comment top

A recent report on complexes of bis(diphenylphosphino)methane with univalent coinage metals details the structure of the 1:1 adduct of the ligand with silver trifluoroacetate. The dinuclear molecule has the ligand binding to two carboxylate-bound silver atoms, who geometry is best described as being T-shaped (Effendy et al., 2005). Replacing the trifluoroacetate ion by the chlorodifluoroacetate ion gives the isostructural title compound (I). There are two formula units in the unit cell (Figs. 1 and 2). One of the unique chlorodifluromethyl groups is ordered whereas the other is disordered.

Related literature top

The compound is isostructural with [Ag(O2CCF3)(C6H5)2PCH2P(C6H5)2]2, see: Effendy et al. (2005). The report also provides background literature on complexes of bis(diphenylphosphino)methane with univalent coinage metals.

Experimental top

Silver chlorodifluoroacetate was prepared in situ from silver oxide (1.20 g, 5 mmol) and chlorodifluoroacetic acid (0.65 g, 5 mmol) in acetone (50 ml). The reactants were heated until the silver oxide dissolved completely. To the brown solution was added bis(diphenylphosphino)methane (3.84 g, 10 mmol) dissolved in acetone (50 ml). The mixture was heated for 30 min; the colorless filtered solution yielded prism-shaped crystals in 60% yield.

Refinement top

Carbon-bound H-atoms were placed in calculated positions (C—H 0.95 to 0.99 Å) and were included in the refinement in the riding model approximation, with U(H) set to 1.2Ueq(C).

There is minor disorder in the chlorodifluoromethyl groups. For both the ordered and disordered groups, the C–Cl distances were restrained to within 0.01 Å of each other, as were the C–F distances. The Cl···F distances as well as the F···F distances were similarly restrained. The Cl1 atom is near the F1' atom, the Cl1' atom near the F1 atom and the F2 atom near the F2' atom; for these pairs, the temperature factors were restrained to be the same. The ansiotropic temperature factors of the Cl1, F1 and F2 atoms were restrained to be nearly isotropic.

The largest peak and deepest holes area in the vicinity of the diordered chlorodifluoromethyl group.

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2008).

Figures top
[Figure 1] Fig. 1. 70% Probability thermal ellipsoid plot of one independent formula unit of (I). Hydrogen atoms are drawn as spheres of arbitrary radius. The disorder is not shown.
[Figure 2] Fig. 2. 70% Probability thermal ellipsoid plot of the ither independent formula unit of (I). Hydrogen atoms are drawn as spheres of arbitrary radius.
Bis[µ-bis(diphenylphosphino)methane- κ2P:P']bis[(chlorodifluoroacetato- κO)silver(I)](Ag—Ag) top
Crystal data top
[Ag2(C2ClF2O2)2(C25H22P2)2]Z = 2
Mr = 1243.41F(000) = 1248
Triclinic, P1Dx = 1.619 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 10.8127 (3) ÅCell parameters from 4611 reflections
b = 14.4911 (3) Åθ = 2.3–25.1°
c = 17.2340 (3) ŵ = 1.06 mm1
α = 83.040 (1)°T = 100 K
β = 86.477 (1)°Block, colorless
γ = 72.188 (1)°0.30 × 0.20 × 0.15 mm
V = 2551.1 (1) Å3
Data collection top
Bruker SMART APEXII
diffractometer
11567 independent reflections
Radiation source: fine-focus sealed tube8338 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.066
ω scansθmax = 27.5°, θmin = 1.2°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1411
Tmin = 0.648, Tmax = 0.857k = 1818
31942 measured reflectionsl = 2222
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)] = 0.045Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.112H-atom parameters constrained
S = 1.01 w = 1/[σ2(Fo2) + (0.0475P)2 + 0.1513P]
where P = (Fo2 + 2Fc2)/3
11567 reflections(Δ/σ)max = 0.001
641 parametersΔρmax = 0.91 e Å3
54 restraintsΔρmin = 1.05 e Å3
Crystal data top
[Ag2(C2ClF2O2)2(C25H22P2)2]γ = 72.188 (1)°
Mr = 1243.41V = 2551.1 (1) Å3
Triclinic, P1Z = 2
a = 10.8127 (3) ÅMo Kα radiation
b = 14.4911 (3) ŵ = 1.06 mm1
c = 17.2340 (3) ÅT = 100 K
α = 83.040 (1)°0.30 × 0.20 × 0.15 mm
β = 86.477 (1)°
Data collection top
Bruker SMART APEXII
diffractometer
11567 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
8338 reflections with I > 2σ(I)
Tmin = 0.648, Tmax = 0.857Rint = 0.066
31942 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.04554 restraints
wR(F2) = 0.112H-atom parameters constrained
S = 1.01Δρmax = 0.91 e Å3
11567 reflectionsΔρmin = 1.05 e Å3
641 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
Ag10.57141 (3)0.89080 (2)1.025045 (18)0.01359 (9)
Ag20.44457 (3)0.57795 (2)0.435262 (17)0.01308 (9)
P10.36794 (11)0.90512 (8)1.09660 (6)0.0128 (2)
P20.21898 (11)1.08082 (8)0.99185 (6)0.0126 (2)
P30.22156 (11)0.57580 (8)0.45928 (6)0.0123 (2)
P40.33747 (11)0.49679 (8)0.61526 (6)0.0123 (2)
Cl10.4662 (5)0.6779 (3)0.79374 (16)0.0304 (8)0.528 (4)
Cl1'0.4581 (6)0.5832 (3)0.9291 (2)0.0379 (9)0.472 (4)
Cl20.57724 (14)0.91381 (9)0.36753 (7)0.0349 (3)
F10.4587 (11)0.6087 (7)0.9329 (5)0.0379 (9)0.528 (4)
F20.6495 (6)0.5949 (9)0.8867 (7)0.057 (3)0.528 (4)
F1'0.4795 (11)0.6915 (7)0.8078 (4)0.0304 (8)0.47
F2'0.6572 (6)0.6182 (9)0.8661 (8)0.057 (3)0.47
F30.3672 (3)0.93038 (18)0.44623 (16)0.0303 (7)
F40.5391 (3)0.89416 (18)0.51371 (14)0.0281 (7)
O10.6050 (3)0.7406 (2)0.97176 (19)0.0252 (8)
O20.4233 (3)0.8250 (2)0.90831 (18)0.0250 (8)
O30.4269 (3)0.7468 (2)0.40995 (17)0.0194 (7)
O40.5974 (3)0.7093 (2)0.48919 (17)0.0210 (7)
C10.5177 (5)0.7528 (3)0.9251 (3)0.0177 (10)
C20.5279 (4)0.6620 (3)0.8834 (2)0.0320 (13)
C30.3471 (4)0.7884 (3)1.1364 (2)0.0134 (9)
C40.3135 (5)0.7311 (3)1.0871 (2)0.0182 (10)
H40.29840.75441.03350.022*
C50.3020 (5)0.6412 (3)1.1149 (3)0.0203 (10)
H50.27850.60301.08070.024*
C60.3245 (4)0.6058 (3)1.1930 (3)0.0195 (10)
H60.31590.54381.21250.023*
C70.3599 (4)0.6621 (3)1.2422 (3)0.0192 (10)
H70.37570.63811.29560.023*
C80.3725 (4)0.7528 (3)1.2146 (2)0.0176 (10)
H80.39810.79031.24860.021*
C90.3251 (4)0.9819 (3)1.1755 (2)0.0151 (9)
C100.2197 (5)0.9807 (3)1.2262 (2)0.0196 (10)
H100.16970.93851.22030.023*
C110.1883 (5)1.0417 (3)1.2856 (3)0.0247 (11)
H110.11771.04011.32080.030*
C120.2601 (5)1.1050 (3)1.2934 (3)0.0284 (12)
H120.23871.14641.33410.034*
C130.3617 (5)1.1072 (3)1.2422 (3)0.0250 (11)
H130.40941.15151.24670.030*
C140.3950 (5)1.0457 (3)1.1842 (3)0.0197 (10)
H140.46661.04701.14970.024*
C150.2313 (4)0.9546 (3)1.0303 (2)0.0147 (9)
H15A0.14960.95271.05880.018*
H15B0.24400.91410.98650.018*
C160.0933 (4)1.1592 (3)1.0494 (2)0.0161 (9)
C170.0165 (5)1.1347 (3)1.0790 (2)0.0213 (10)
H170.02181.07121.07510.026*
C180.1181 (5)1.2016 (4)1.1138 (3)0.0282 (12)
H180.19161.18371.13520.034*
C190.1112 (5)1.2954 (4)1.1172 (3)0.0331 (13)
H190.18131.34191.14020.040*
C200.0046 (5)1.3213 (4)1.0877 (3)0.0312 (13)
H200.00151.38571.09010.037*
C210.1000 (5)1.2531 (3)1.0541 (3)0.0257 (11)
H210.17491.27061.03470.031*
C220.1465 (4)1.0963 (3)0.8966 (2)0.0136 (9)
C230.0346 (4)1.1716 (3)0.8754 (2)0.0153 (9)
H230.01201.21310.91290.018*
C240.0092 (5)1.1862 (3)0.7991 (2)0.0192 (10)
H240.08541.23770.78470.023*
C250.0581 (5)1.1261 (3)0.7447 (2)0.0201 (10)
H250.02841.13630.69270.024*
C260.1690 (5)1.0508 (3)0.7656 (3)0.0228 (11)
H260.21481.00920.72790.027*
C270.2132 (5)1.0358 (3)0.8403 (2)0.0175 (10)
H270.28960.98410.85400.021*
C280.5066 (4)0.7659 (3)0.4504 (2)0.0159 (9)
C290.4938 (4)0.8749 (3)0.4479 (2)0.0180 (10)
C300.0954 (4)0.6894 (3)0.4722 (2)0.0147 (9)
C310.1256 (4)0.7772 (3)0.4582 (2)0.0150 (9)
H310.21120.77740.44230.018*
C320.0285 (5)0.8645 (3)0.4677 (2)0.0186 (10)
H320.04850.92440.45870.022*
C330.0963 (5)0.8647 (3)0.4902 (3)0.0225 (11)
H330.16150.92480.49630.027*
C340.1273 (5)0.7780 (3)0.5038 (3)0.0230 (11)
H340.21330.77820.51910.028*
C350.0303 (5)0.6904 (3)0.4948 (2)0.0189 (10)
H350.05070.63070.50430.023*
C360.1645 (4)0.5244 (3)0.3820 (2)0.0129 (9)
C370.0671 (4)0.5790 (3)0.3314 (2)0.0156 (9)
H370.02060.64430.33990.019*
C380.0372 (5)0.5388 (4)0.2684 (3)0.0244 (11)
H380.02900.57670.23370.029*
C390.1038 (5)0.4439 (3)0.2564 (3)0.0231 (11)
H390.08330.41650.21330.028*
C400.1998 (5)0.3883 (3)0.3063 (3)0.0231 (11)
H400.24470.32270.29810.028*
C410.2302 (5)0.4287 (3)0.3684 (3)0.0199 (10)
H410.29720.39050.40240.024*
C420.2131 (4)0.4938 (3)0.5487 (2)0.0137 (9)
H42A0.12590.51550.57400.016*
H42B0.22860.42660.53540.016*
C430.2848 (4)0.6229 (3)0.6363 (2)0.0134 (9)
C440.1606 (5)0.6641 (3)0.6664 (2)0.0200 (10)
H440.10480.62480.67920.024*
C450.1174 (5)0.7612 (3)0.6780 (3)0.0274 (12)
H450.03290.78840.69950.033*
C460.1990 (6)0.8198 (3)0.6579 (3)0.0313 (13)
H460.16880.88730.66440.038*
C470.3228 (6)0.7794 (3)0.6289 (3)0.0306 (13)
H470.37810.81910.61590.037*
C480.3675 (5)0.6805 (3)0.6185 (3)0.0219 (10)
H480.45360.65260.59940.026*
C490.3078 (4)0.4276 (3)0.7060 (2)0.0132 (9)
C500.2893 (4)0.3372 (3)0.7047 (2)0.0159 (9)
H500.28520.31390.65600.019*
C510.2767 (4)0.2804 (3)0.7737 (3)0.0182 (10)
H510.26340.21890.77220.022*
C520.2837 (5)0.3134 (3)0.8447 (3)0.0220 (10)
H520.27370.27500.89200.026*
C530.3050 (5)0.4020 (3)0.8470 (3)0.0220 (10)
H530.31210.42370.89590.026*
C540.3161 (5)0.4597 (3)0.7781 (2)0.0175 (10)
H540.32950.52120.78000.021*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ag10.01193 (18)0.01480 (16)0.01485 (16)0.00570 (13)0.00048 (13)0.00078 (12)
Ag20.01034 (18)0.01539 (16)0.01353 (16)0.00444 (13)0.00060 (13)0.00059 (12)
P10.0113 (6)0.0147 (5)0.0135 (5)0.0060 (5)0.0002 (4)0.0003 (4)
P20.0111 (6)0.0137 (5)0.0135 (5)0.0050 (5)0.0003 (4)0.0001 (4)
P30.0109 (6)0.0130 (5)0.0129 (5)0.0037 (5)0.0005 (4)0.0009 (4)
P40.0109 (6)0.0134 (5)0.0130 (5)0.0049 (4)0.0006 (4)0.0003 (4)
Cl10.0465 (17)0.0385 (15)0.0165 (13)0.0238 (11)0.0117 (11)0.0080 (11)
Cl1'0.0584 (16)0.025 (2)0.0436 (13)0.0322 (17)0.0145 (11)0.0131 (13)
Cl20.0471 (9)0.0215 (6)0.0367 (7)0.0159 (6)0.0141 (6)0.0016 (5)
F10.0584 (16)0.025 (2)0.0436 (13)0.0322 (17)0.0145 (11)0.0131 (13)
F20.038 (3)0.042 (5)0.091 (6)0.000 (2)0.001 (3)0.041 (4)
F1'0.0465 (17)0.0385 (15)0.0165 (13)0.0238 (11)0.0117 (11)0.0080 (11)
F2'0.038 (3)0.042 (5)0.091 (6)0.000 (2)0.001 (3)0.041 (4)
F30.0203 (17)0.0193 (14)0.0465 (18)0.0022 (12)0.0024 (14)0.0060 (12)
F40.0327 (18)0.0242 (14)0.0307 (15)0.0107 (13)0.0047 (13)0.0084 (12)
O10.020 (2)0.0295 (18)0.0294 (18)0.0095 (15)0.0020 (15)0.0104 (14)
O20.023 (2)0.0186 (16)0.0300 (18)0.0023 (15)0.0043 (15)0.0004 (14)
O30.0178 (18)0.0216 (16)0.0220 (16)0.0112 (14)0.0002 (14)0.0012 (13)
O40.0201 (19)0.0148 (15)0.0239 (17)0.0009 (14)0.0021 (14)0.0031 (13)
C10.021 (3)0.017 (2)0.019 (2)0.013 (2)0.009 (2)0.0082 (18)
C20.023 (3)0.033 (3)0.044 (3)0.007 (2)0.001 (3)0.021 (2)
C30.007 (2)0.016 (2)0.017 (2)0.0036 (18)0.0012 (17)0.0001 (16)
C40.020 (3)0.019 (2)0.015 (2)0.006 (2)0.0015 (19)0.0017 (17)
C50.022 (3)0.017 (2)0.022 (2)0.005 (2)0.002 (2)0.0024 (18)
C60.014 (3)0.019 (2)0.024 (2)0.0048 (19)0.0042 (19)0.0008 (18)
C70.016 (3)0.021 (2)0.019 (2)0.004 (2)0.0037 (19)0.0054 (18)
C80.012 (2)0.021 (2)0.018 (2)0.0034 (19)0.0001 (18)0.0004 (17)
C90.016 (2)0.012 (2)0.016 (2)0.0035 (18)0.0012 (18)0.0003 (16)
C100.015 (3)0.020 (2)0.021 (2)0.003 (2)0.0019 (19)0.0012 (18)
C110.025 (3)0.018 (2)0.027 (3)0.002 (2)0.009 (2)0.0006 (19)
C120.039 (3)0.021 (2)0.024 (3)0.007 (2)0.001 (2)0.008 (2)
C130.034 (3)0.021 (2)0.024 (2)0.015 (2)0.001 (2)0.0048 (19)
C140.020 (3)0.022 (2)0.018 (2)0.008 (2)0.0010 (19)0.0002 (18)
C150.017 (2)0.013 (2)0.015 (2)0.0049 (18)0.0005 (18)0.0024 (16)
C160.014 (2)0.024 (2)0.011 (2)0.0063 (19)0.0009 (18)0.0048 (17)
C170.021 (3)0.026 (2)0.018 (2)0.009 (2)0.004 (2)0.0018 (18)
C180.016 (3)0.044 (3)0.024 (3)0.008 (2)0.004 (2)0.007 (2)
C190.022 (3)0.045 (3)0.032 (3)0.003 (3)0.004 (2)0.024 (2)
C200.019 (3)0.029 (3)0.045 (3)0.000 (2)0.004 (2)0.020 (2)
C210.024 (3)0.027 (3)0.031 (3)0.012 (2)0.001 (2)0.009 (2)
C220.016 (2)0.014 (2)0.013 (2)0.0093 (18)0.0002 (18)0.0012 (16)
C230.010 (2)0.015 (2)0.020 (2)0.0039 (18)0.0005 (18)0.0000 (17)
C240.014 (3)0.023 (2)0.022 (2)0.010 (2)0.0038 (19)0.0060 (18)
C250.019 (3)0.030 (3)0.014 (2)0.012 (2)0.0054 (19)0.0037 (18)
C260.028 (3)0.025 (2)0.019 (2)0.014 (2)0.004 (2)0.0053 (19)
C270.016 (3)0.017 (2)0.021 (2)0.0079 (19)0.0008 (19)0.0000 (17)
C280.015 (3)0.012 (2)0.021 (2)0.0068 (19)0.0046 (19)0.0003 (17)
C290.016 (3)0.015 (2)0.024 (2)0.0062 (19)0.0003 (19)0.0011 (17)
C300.016 (2)0.013 (2)0.014 (2)0.0036 (18)0.0009 (18)0.0013 (16)
C310.011 (2)0.021 (2)0.013 (2)0.0050 (19)0.0018 (17)0.0012 (17)
C320.020 (3)0.012 (2)0.020 (2)0.0007 (19)0.004 (2)0.0034 (17)
C330.020 (3)0.019 (2)0.023 (2)0.004 (2)0.002 (2)0.0086 (19)
C340.013 (3)0.031 (3)0.023 (2)0.003 (2)0.001 (2)0.006 (2)
C350.018 (3)0.021 (2)0.020 (2)0.009 (2)0.0002 (19)0.0050 (18)
C360.013 (2)0.015 (2)0.014 (2)0.0087 (18)0.0016 (17)0.0031 (16)
C370.013 (2)0.017 (2)0.015 (2)0.0030 (19)0.0003 (18)0.0002 (17)
C380.019 (3)0.038 (3)0.016 (2)0.009 (2)0.001 (2)0.001 (2)
C390.022 (3)0.038 (3)0.018 (2)0.021 (2)0.002 (2)0.007 (2)
C400.030 (3)0.019 (2)0.027 (2)0.016 (2)0.004 (2)0.0079 (19)
C410.023 (3)0.018 (2)0.018 (2)0.006 (2)0.002 (2)0.0007 (17)
C420.015 (2)0.014 (2)0.013 (2)0.0052 (18)0.0007 (17)0.0006 (16)
C430.018 (3)0.0097 (19)0.013 (2)0.0049 (18)0.0027 (18)0.0007 (15)
C440.019 (3)0.022 (2)0.019 (2)0.007 (2)0.0006 (19)0.0004 (18)
C450.026 (3)0.025 (3)0.028 (3)0.001 (2)0.003 (2)0.010 (2)
C460.047 (4)0.016 (2)0.030 (3)0.007 (2)0.000 (3)0.009 (2)
C470.050 (4)0.025 (3)0.026 (3)0.024 (3)0.001 (3)0.005 (2)
C480.024 (3)0.023 (2)0.022 (2)0.012 (2)0.002 (2)0.0037 (19)
C490.007 (2)0.017 (2)0.013 (2)0.0013 (18)0.0032 (17)0.0004 (16)
C500.011 (2)0.019 (2)0.018 (2)0.0071 (19)0.0013 (18)0.0008 (17)
C510.011 (2)0.014 (2)0.026 (2)0.0019 (18)0.0048 (19)0.0013 (18)
C520.021 (3)0.023 (2)0.020 (2)0.006 (2)0.003 (2)0.0061 (18)
C530.022 (3)0.028 (3)0.016 (2)0.008 (2)0.001 (2)0.0031 (19)
C540.020 (3)0.014 (2)0.018 (2)0.0048 (19)0.0010 (19)0.0026 (17)
Geometric parameters (Å, º) top
Ag1—O12.382 (3)C18—H180.9500
Ag1—P12.4194 (12)C19—C201.370 (7)
Ag1—P2i2.419 (1)C19—H190.9500
Ag1—Ag1i3.1078 (6)C20—C211.402 (7)
Ag2—O32.383 (3)C20—H200.9500
Ag2—P32.430 (1)C21—H210.9500
Ag2—P4ii2.429 (1)C22—C231.392 (6)
Ag2—Ag2ii2.9950 (6)C22—C271.401 (6)
P1—C91.810 (4)C23—C241.395 (6)
P1—C31.821 (4)C23—H230.9500
P1—C151.834 (4)C24—C251.376 (6)
P2—C161.813 (4)C24—H240.9500
P2—C221.822 (4)C25—C261.385 (6)
P2—C151.836 (4)C25—H250.9500
P2—Ag1i2.4188 (12)C26—C271.370 (6)
P3—C301.816 (4)C26—H260.9500
P3—C361.825 (4)C27—H270.9500
P3—C421.843 (4)C28—C291.539 (5)
P4—C431.816 (4)C30—C351.387 (6)
P4—C491.818 (4)C30—C311.397 (6)
P4—C421.834 (4)C31—C321.395 (6)
P4—Ag2ii2.4291 (12)C31—H310.9500
Cl1—C21.683 (5)C32—C331.380 (7)
Cl1'—C21.652 (5)C32—H320.9500
Cl2—C291.737 (4)C33—C341.387 (6)
F1—C21.413 (6)C33—H330.9500
F2—C21.375 (7)C34—C351.395 (6)
F1'—C21.402 (6)C34—H340.9500
F2'—C21.378 (7)C35—H350.9500
F3—C291.360 (4)C36—C371.390 (6)
F4—C291.354 (4)C36—C411.392 (6)
O1—C11.235 (5)C37—C381.392 (6)
O2—C11.236 (5)C37—H370.9500
O3—C281.254 (5)C38—C391.378 (7)
O4—C281.240 (5)C38—H380.9500
C1—C21.547 (6)C39—C401.377 (7)
C3—C41.392 (6)C39—H390.9500
C3—C81.397 (5)C40—C411.382 (6)
C4—C51.372 (6)C40—H400.9500
C4—H40.9500C41—H410.9500
C5—C61.388 (6)C42—H42A0.9900
C5—H50.9500C42—H42B0.9900
C6—C71.389 (6)C43—C441.388 (6)
C6—H60.9500C43—C481.397 (6)
C7—C81.386 (6)C44—C451.376 (6)
C7—H70.9500C44—H440.9500
C8—H80.9500C45—C461.402 (7)
C9—C141.386 (6)C45—H450.9500
C9—C101.396 (6)C46—C471.376 (8)
C10—C111.390 (6)C46—H460.9500
C10—H100.9500C47—C481.395 (6)
C11—C121.393 (7)C47—H470.9500
C11—H110.9500C48—H480.9500
C12—C131.373 (7)C49—C501.387 (6)
C12—H120.9500C49—C541.396 (6)
C13—C141.378 (6)C50—C511.387 (6)
C13—H130.9500C50—H500.9500
C14—H140.9500C51—C521.380 (6)
C15—H15A0.9900C51—H510.9500
C15—H15B0.9900C52—C531.378 (6)
C16—C171.390 (6)C52—H520.9500
C16—C211.397 (6)C53—C541.387 (6)
C17—C181.384 (7)C53—H530.9500
C17—H170.9500C54—H540.9500
C18—C191.392 (7)
O1—Ag1—P1100.92 (9)C21—C20—H20119.9
O1—Ag1—P2i103.78 (9)C16—C21—C20119.4 (5)
P1—Ag1—P2i151.19 (4)C16—C21—H21120.3
O1—Ag1—Ag1i136.10 (8)C20—C21—H21120.3
P2i—Ag1—Ag1i91.48 (3)C23—C22—C27118.9 (4)
P1—Ag1—Ag1i80.72 (3)C23—C22—P2122.4 (3)
O3—Ag2—P3104.14 (8)C27—C22—P2118.4 (3)
O3—Ag2—P4ii101.43 (8)C22—C23—C24120.1 (4)
P3—Ag2—P4ii149.67 (4)C22—C23—H23120.0
O3—Ag2—Ag2ii134.22 (7)C24—C23—H23120.0
P4ii—Ag2—Ag2ii78.04 (3)C25—C24—C23120.0 (4)
P3—Ag2—Ag2ii95.23 (3)C25—C24—H24120.0
C9—P1—C3105.99 (19)C23—C24—H24120.0
C9—P1—C15103.98 (19)C24—C25—C26120.1 (4)
C3—P1—C15102.13 (19)C24—C25—H25119.9
C9—P1—Ag1119.10 (15)C26—C25—H25119.9
C3—P1—Ag1113.66 (15)C27—C26—C25120.4 (4)
C15—P1—Ag1110.26 (15)C27—C26—H26119.8
C16—P2—C22103.7 (2)C25—C26—H26119.8
C16—P2—C15106.9 (2)C26—C27—C22120.5 (4)
C22—P2—C15104.17 (18)C26—C27—H27119.8
C16—P2—Ag1i118.83 (15)C22—C27—H27119.8
C22—P2—Ag1i109.27 (15)O4—C28—O3129.2 (4)
C15—P2—Ag1i112.61 (15)O4—C28—C29115.7 (4)
C30—P3—C36105.1 (2)O3—C28—C29115.0 (4)
C30—P3—C42105.46 (19)F4—C29—F3104.5 (3)
C36—P3—C42104.87 (18)F4—C29—C28111.2 (3)
C30—P3—Ag2119.03 (15)F3—C29—C28111.3 (3)
C36—P3—Ag2112.02 (15)F4—C29—Cl2108.8 (3)
C42—P3—Ag2109.25 (15)F3—C29—Cl2109.3 (3)
C43—P4—C49104.85 (19)C28—C29—Cl2111.5 (3)
C43—P4—C42102.48 (19)C35—C30—C31119.7 (4)
C49—P4—C42105.27 (19)C35—C30—P3121.1 (3)
C43—P4—Ag2ii121.28 (15)C31—C30—P3119.3 (3)
C49—P4—Ag2ii109.90 (14)C32—C31—C30119.2 (4)
C42—P4—Ag2ii111.71 (14)C32—C31—H31120.4
C1—O1—Ag1107.5 (3)C30—C31—H31120.4
C28—O3—Ag2109.5 (3)C33—C32—C31120.7 (4)
O1—C1—O2130.1 (4)C33—C32—H32119.7
O1—C1—C2113.9 (4)C31—C32—H32119.7
O2—C1—C2115.9 (4)C32—C33—C34120.5 (4)
F2'—C2—F1'100.4 (6)C32—C33—H33119.8
F2—C2—F199.3 (6)C34—C33—H33119.8
F2—C2—C1113.2 (7)C33—C34—C35119.1 (5)
F2'—C2—C1108.0 (8)C33—C34—H34120.5
F1'—C2—C1109.5 (5)C35—C34—H34120.5
F1—C2—C1105.0 (5)C30—C35—C34120.9 (4)
F2'—C2—Cl1'111.8 (6)C30—C35—H35119.6
F1'—C2—Cl1'109.7 (4)C34—C35—H35119.6
C1—C2—Cl1'116.3 (3)C37—C36—C41118.4 (4)
F2—C2—Cl1111.4 (6)C37—C36—P3123.0 (3)
F1—C2—Cl1106.8 (5)C41—C36—P3118.2 (3)
C1—C2—Cl1118.8 (3)C36—C37—C38120.5 (4)
C4—C3—C8119.5 (4)C36—C37—H37119.7
C4—C3—P1119.6 (3)C38—C37—H37119.7
C8—C3—P1120.8 (3)C39—C38—C37119.8 (4)
C5—C4—C3120.8 (4)C39—C38—H38120.1
C5—C4—H4119.6C37—C38—H38120.1
C3—C4—H4119.6C40—C39—C38120.6 (4)
C4—C5—C6120.3 (4)C40—C39—H39119.7
C4—C5—H5119.9C38—C39—H39119.7
C6—C5—H5119.9C39—C40—C41119.6 (4)
C5—C6—C7119.2 (4)C39—C40—H40120.2
C5—C6—H6120.4C41—C40—H40120.2
C7—C6—H6120.4C40—C41—C36121.2 (4)
C8—C7—C6121.1 (4)C40—C41—H41119.4
C8—C7—H7119.5C36—C41—H41119.4
C6—C7—H7119.5P4—C42—P3108.4 (2)
C7—C8—C3119.1 (4)P4—C42—H42A110.0
C7—C8—H8120.4P3—C42—H42A110.0
C3—C8—H8120.4P4—C42—H42B110.0
C14—C9—C10119.2 (4)P3—C42—H42B110.0
C14—C9—P1119.6 (4)H42A—C42—H42B108.4
C10—C9—P1121.2 (3)C44—C43—C48119.6 (4)
C11—C10—C9119.7 (4)C44—C43—P4120.6 (3)
C11—C10—H10120.1C48—C43—P4119.7 (4)
C9—C10—H10120.1C45—C44—C43120.8 (4)
C10—C11—C12120.2 (5)C45—C44—H44119.6
C10—C11—H11119.9C43—C44—H44119.6
C12—C11—H11119.9C44—C45—C46119.6 (5)
C13—C12—C11119.8 (4)C44—C45—H45120.2
C13—C12—H12120.1C46—C45—H45120.2
C11—C12—H12120.1C47—C46—C45119.9 (4)
C12—C13—C14120.4 (5)C47—C46—H46120.0
C12—C13—H13119.8C45—C46—H46120.0
C14—C13—H13119.8C46—C47—C48120.5 (5)
C13—C14—C9120.8 (5)C46—C47—H47119.8
C13—C14—H14119.6C48—C47—H47119.8
C9—C14—H14119.6C47—C48—C43119.5 (5)
P1—C15—P2110.3 (2)C47—C48—H48120.3
P1—C15—H15A109.6C43—C48—H48120.3
P2—C15—H15A109.6C50—C49—C54118.8 (4)
P1—C15—H15B109.6C50—C49—P4120.2 (3)
P2—C15—H15B109.6C54—C49—P4120.7 (3)
H15A—C15—H15B108.1C51—C50—C49120.7 (4)
C17—C16—C21119.4 (4)C51—C50—H50119.7
C17—C16—P2122.7 (3)C49—C50—H50119.7
C21—C16—P2117.2 (4)C52—C51—C50119.9 (4)
C18—C17—C16120.9 (5)C52—C51—H51120.0
C18—C17—H17119.5C50—C51—H51120.0
C16—C17—H17119.5C53—C52—C51120.1 (4)
C17—C18—C19119.2 (5)C53—C52—H52120.0
C17—C18—H18120.4C51—C52—H52120.0
C19—C18—H18120.4C52—C53—C54120.2 (4)
C20—C19—C18120.8 (5)C52—C53—H53119.9
C20—C19—H19119.6C54—C53—H53119.9
C18—C19—H19119.6C53—C54—C49120.2 (4)
C19—C20—C21120.2 (5)C53—C54—H54119.9
C19—C20—H20119.9C49—C54—H54119.9
O1—Ag1—P1—C9158.28 (17)C19—C20—C21—C161.4 (7)
P2i—Ag1—P1—C99.62 (18)C16—P2—C22—C2314.1 (4)
Ag1i—Ag1—P1—C966.32 (15)C15—P2—C22—C23125.9 (4)
O1—Ag1—P1—C332.26 (17)Ag1i—P2—C22—C23113.5 (3)
P2i—Ag1—P1—C3116.40 (16)C16—P2—C22—C27172.3 (3)
Ag1i—Ag1—P1—C3167.66 (15)C15—P2—C22—C2760.5 (4)
O1—Ag1—P1—C1581.72 (16)Ag1i—P2—C22—C2760.0 (3)
P2i—Ag1—P1—C15129.63 (15)C27—C22—C23—C240.3 (6)
Ag1i—Ag1—P1—C1553.68 (14)P2—C22—C23—C24173.3 (3)
O3—Ag2—P3—C3011.10 (17)C22—C23—C24—C250.1 (6)
P4ii—Ag2—P3—C30157.73 (15)C23—C24—C25—C260.3 (7)
Ag2ii—Ag2—P3—C30127.08 (15)C24—C25—C26—C270.5 (7)
O3—Ag2—P3—C36112.04 (16)C25—C26—C27—C220.3 (7)
P4ii—Ag2—P3—C3634.59 (17)C23—C22—C27—C260.1 (6)
Ag2ii—Ag2—P3—C36109.78 (14)P2—C22—C27—C26173.7 (3)
O3—Ag2—P3—C42132.21 (16)Ag2—O3—C28—O411.0 (6)
P4ii—Ag2—P3—C4281.16 (16)Ag2—O3—C28—C29172.5 (3)
Ag2ii—Ag2—P3—C425.97 (14)O4—C28—C29—F429.1 (5)
P2i—Ag1—O1—C1129.4 (3)O3—C28—C29—F4153.9 (4)
P1—Ag1—O1—C165.6 (3)O4—C28—C29—F3145.2 (4)
Ag1i—Ag1—O1—C122.3 (4)O3—C28—C29—F337.9 (5)
P4ii—Ag2—O3—C2865.3 (3)O4—C28—C29—Cl292.5 (4)
P3—Ag2—O3—C28131.1 (3)O3—C28—C29—Cl284.4 (4)
Ag2ii—Ag2—O3—C2819.0 (3)C36—P3—C30—C3560.9 (4)
Ag1—O1—C1—O23.4 (6)C42—P3—C30—C3549.6 (4)
Ag1—O1—C1—C2178.4 (3)Ag2—P3—C30—C35172.6 (3)
O1—C1—C2—F218.6 (7)C36—P3—C30—C31118.2 (3)
O2—C1—C2—F2163.0 (6)C42—P3—C30—C31131.3 (3)
O1—C1—C2—F2'39.4 (7)Ag2—P3—C30—C318.2 (4)
O2—C1—C2—F2'142.2 (6)C35—C30—C31—C320.5 (6)
O1—C1—C2—F1'147.8 (6)P3—C30—C31—C32179.7 (3)
O2—C1—C2—F1'33.8 (7)C30—C31—C32—C330.5 (6)
O1—C1—C2—F188.6 (6)C31—C32—C33—C340.2 (7)
O2—C1—C2—F189.8 (6)C32—C33—C34—C350.2 (7)
O1—C1—C2—Cl1'87.2 (5)C31—C30—C35—C340.1 (6)
O2—C1—C2—Cl1'91.3 (5)P3—C30—C35—C34179.2 (3)
O1—C1—C2—Cl1152.1 (4)C33—C34—C35—C300.3 (7)
O2—C1—C2—Cl129.5 (6)C30—P3—C36—C3717.4 (4)
C9—P1—C3—C4150.5 (4)C42—P3—C36—C37128.4 (4)
C15—P1—C3—C441.9 (4)Ag2—P3—C36—C37113.2 (4)
Ag1—P1—C3—C476.9 (4)C30—P3—C36—C41169.0 (3)
C9—P1—C3—C833.6 (4)C42—P3—C36—C4158.0 (4)
C15—P1—C3—C8142.2 (4)Ag2—P3—C36—C4160.3 (4)
Ag1—P1—C3—C899.1 (4)C41—C36—C37—C380.5 (7)
C8—C3—C4—C51.6 (7)P3—C36—C37—C38173.0 (4)
P1—C3—C4—C5177.5 (4)C36—C37—C38—C390.6 (7)
C3—C4—C5—C60.3 (7)C37—C38—C39—C400.1 (7)
C4—C5—C6—C70.6 (7)C38—C39—C40—C410.7 (7)
C5—C6—C7—C80.2 (7)C39—C40—C41—C360.7 (7)
C6—C7—C8—C31.0 (7)C37—C36—C41—C400.1 (7)
C4—C3—C8—C71.9 (7)P3—C36—C41—C40174.0 (4)
P1—C3—C8—C7177.8 (3)C43—P4—C42—P363.2 (3)
C3—P1—C9—C14142.2 (3)C49—P4—C42—P3172.6 (2)
C15—P1—C9—C14110.6 (4)Ag2ii—P4—C42—P368.2 (2)
Ag1—P1—C9—C1412.6 (4)C30—P3—C42—P497.8 (2)
C3—P1—C9—C1040.2 (4)C36—P3—C42—P4151.5 (2)
C15—P1—C9—C1067.0 (4)Ag2—P3—C42—P431.2 (2)
Ag1—P1—C9—C10169.8 (3)C49—P4—C43—C4454.0 (4)
C14—C9—C10—C111.5 (6)C42—P4—C43—C4455.8 (4)
P1—C9—C10—C11179.1 (3)Ag2ii—P4—C43—C44178.9 (3)
C9—C10—C11—C121.3 (7)C49—P4—C43—C48129.3 (3)
C10—C11—C12—C130.2 (7)C42—P4—C43—C48121.0 (3)
C11—C12—C13—C141.5 (7)Ag2ii—P4—C43—C484.3 (4)
C12—C13—C14—C91.3 (7)C48—C43—C44—C450.8 (6)
C10—C9—C14—C130.2 (6)P4—C43—C44—C45176.0 (3)
P1—C9—C14—C13177.9 (3)C43—C44—C45—C461.1 (7)
C9—P1—C15—P262.7 (3)C44—C45—C46—C471.9 (7)
C3—P1—C15—P2172.8 (2)C45—C46—C47—C480.7 (7)
Ag1—P1—C15—P266.1 (2)C46—C47—C48—C431.2 (7)
C16—P2—C15—P199.2 (2)C44—C43—C48—C472.0 (6)
C22—P2—C15—P1151.4 (2)P4—C43—C48—C47174.8 (3)
Ag1i—P2—C15—P133.1 (2)C43—P4—C49—C50155.4 (4)
C22—P2—C16—C1775.3 (4)C42—P4—C49—C5047.7 (4)
C15—P2—C16—C1734.4 (4)Ag2ii—P4—C49—C5072.7 (4)
Ag1i—P2—C16—C17163.2 (3)C43—P4—C49—C5431.0 (4)
C22—P2—C16—C2195.5 (4)C42—P4—C49—C54138.7 (4)
C15—P2—C16—C21154.8 (3)Ag2ii—P4—C49—C54100.9 (3)
Ag1i—P2—C16—C2126.0 (4)C54—C49—C50—C511.2 (7)
C21—C16—C17—C180.9 (7)P4—C49—C50—C51174.9 (3)
P2—C16—C17—C18171.5 (3)C49—C50—C51—C520.5 (7)
C16—C17—C18—C191.8 (7)C50—C51—C52—C531.0 (7)
C17—C18—C19—C201.1 (7)C51—C52—C53—C541.7 (7)
C18—C19—C20—C210.5 (8)C52—C53—C54—C491.0 (7)
C17—C16—C21—C200.7 (7)C50—C49—C54—C530.5 (7)
P2—C16—C21—C20170.4 (4)P4—C49—C54—C53174.1 (4)
Symmetry codes: (i) x+1, y+2, z+2; (ii) x+1, y+1, z+1.

Experimental details

Crystal data
Chemical formula[Ag2(C2ClF2O2)2(C25H22P2)2]
Mr1243.41
Crystal system, space groupTriclinic, P1
Temperature (K)100
a, b, c (Å)10.8127 (3), 14.4911 (3), 17.2340 (3)
α, β, γ (°)83.040 (1), 86.477 (1), 72.188 (1)
V3)2551.1 (1)
Z2
Radiation typeMo Kα
µ (mm1)1.06
Crystal size (mm)0.30 × 0.20 × 0.15
Data collection
DiffractometerBruker SMART APEXII
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.648, 0.857
No. of measured, independent and
observed [I > 2σ(I)] reflections
31942, 11567, 8338
Rint0.066
(sin θ/λ)max1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.045, 0.112, 1.01
No. of reflections11567
No. of parameters641
No. of restraints54
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.91, 1.05

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2008).

Selected geometric parameters (Å, º) top
Ag1—O12.382 (3)Ag2—O32.383 (3)
Ag1—P12.4194 (12)Ag2—P32.430 (1)
Ag1—P2i2.419 (1)Ag2—P4ii2.429 (1)
O1—Ag1—P1100.92 (9)O3—Ag2—P3104.14 (8)
O1—Ag1—P2i103.78 (9)O3—Ag2—P4ii101.43 (8)
P1—Ag1—P2i151.19 (4)P3—Ag2—P4ii149.67 (4)
Symmetry codes: (i) x+1, y+2, z+2; (ii) x+1, y+1, z+1.
 

Acknowledgements

We thank the University of Malaya for funding this study (SF022155/2007 A) and also for the purchase of the diffractometer.

References

First citationBarbour, L. J. (2001). J. Supramol. Chem. 1, 189–191.  CrossRef CAS Google Scholar
First citationBruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationEffendy, Di Nocola, C., Nitiatmodjo, M., Pettinari, C., Skelton, B. W. & White, A. H. (2005). Inorg. Chim. Acta, 358, 735–747.  CrossRef CAS Google Scholar
First citationSheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationWestrip, S. P. (2008). publCIF. In preparation.  Google Scholar

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