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Acta Crystallogr Sect E Struct Rep Online. 2008 May 1; 64(Pt 5): m717.
Published online 2008 April 26. doi:  10.1107/S1600536808011033
PMCID: PMC2961164

Bis[μ-bis­(diphenyl­phosphino)methane-κ2 P:P′]bis­[(chloro­difluoro­acetato-κO)silver(I)](AgAg)

Abstract

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 [triangle]). The report also provides background literature on complexes of bis­(di­phenyl­phosphino)methane with univalent coinage metals.

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Object name is e-64-0m717-scheme1.jpg

Experimental

Crystal data

  • [Ag2(C2ClF2O2)2(C25H22P2)2]
  • M r = 1243.41
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-0m717-efi1.jpg
  • 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 [triangle]) T min = 0.648, T max = 0.857
  • 31942 measured reflections
  • 11567 independent reflections
  • 8338 reflections with I > 2σ(I)
  • R int = 0.066

Refinement

  • R[F 2 > 2σ(F 2)] = 0.045
  • wR(F 2) = 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

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

Table 1
Selected geometric parameters (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808011033/lh2610sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808011033/lh2610Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

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

supplementary crystallographic information

Comment

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.

Experimental

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

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.

Figures

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.
Fig. 2.
70% Probability thermal ellipsoid plot of the ither independent formula unit of (I). Hydrogen atoms are drawn as spheres of arbitrary radius.

Crystal data

[Ag2(C2ClF2O2)2(C25H22P2)2]Z = 2
Mr = 1243.41F000 = 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 = 2.3–25.1º
c = 17.2340 (3) ŵ = 1.06 mm1
α = 83.040 (1)ºT = 100 (2) K
β = 86.477 (1)ºBlock, colorless
γ = 72.188 (1)º0.30 × 0.20 × 0.15 mm
V = 2551.1 (1) Å3

Data collection

Bruker SMART APEXII diffractometer11567 independent reflections
Radiation source: fine-focus sealed tube8338 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.066
T = 100(2) Kθmax = 27.5º
ω scansθmin = 1.2º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)h = −14→11
Tmin = 0.648, Tmax = 0.857k = −18→18
31942 measured reflectionsl = −22→22

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.045H-atom parameters constrained
wR(F2) = 0.112  w = 1/[σ2(Fo2) + (0.0475P)2 + 0.1513P] where P = (Fo2 + 2Fc2)/3
S = 1.01(Δ/σ)max = 0.001
11567 reflectionsΔρmax = 0.91 e Å3
641 parametersΔρmin = −1.05 e Å3
54 restraintsExtinction correction: none
Primary atom site location: structure-invariant direct methods

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

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)
C17−0.0165 (5)1.1347 (3)1.0790 (2)0.0213 (10)
H17−0.02181.07121.07510.026*
C18−0.1181 (5)1.2016 (4)1.1138 (3)0.0282 (12)
H18−0.19161.18371.13520.034*
C19−0.1112 (5)1.2954 (4)1.1172 (3)0.0331 (13)
H19−0.18131.34191.14020.040*
C20−0.0046 (5)1.3213 (4)1.0877 (3)0.0312 (13)
H20−0.00151.38571.09010.037*
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)
H23−0.01201.21310.91290.018*
C24−0.0092 (5)1.1862 (3)0.7991 (2)0.0192 (10)
H24−0.08541.23770.78470.023*
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*
C33−0.0963 (5)0.8647 (3)0.4902 (3)0.0225 (11)
H33−0.16150.92480.49630.027*
C34−0.1273 (5)0.7780 (3)0.5038 (3)0.0230 (11)
H34−0.21330.77820.51910.028*
C35−0.0303 (5)0.6904 (3)0.4948 (2)0.0189 (10)
H35−0.05070.63070.50430.023*
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)
H38−0.02900.57670.23370.029*
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)

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, °)

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—C9−66.32 (15)C15—P2—C22—C23125.9 (4)
O1—Ag1—P1—C332.26 (17)Ag1i—P2—C22—C23−113.5 (3)
P2i—Ag1—P1—C3−116.40 (16)C16—P2—C22—C27−172.3 (3)
Ag1i—Ag1—P1—C3167.66 (15)C15—P2—C22—C27−60.5 (4)
O1—Ag1—P1—C15−81.72 (16)Ag1i—P2—C22—C2760.0 (3)
P2i—Ag1—P1—C15129.63 (15)C27—C22—C23—C24−0.3 (6)
Ag1i—Ag1—P1—C1553.68 (14)P2—C22—C23—C24173.3 (3)
O3—Ag2—P3—C30−11.10 (17)C22—C23—C24—C250.1 (6)
P4ii—Ag2—P3—C30−157.73 (15)C23—C24—C25—C260.3 (7)
Ag2ii—Ag2—P3—C30127.08 (15)C24—C25—C26—C27−0.5 (7)
O3—Ag2—P3—C36112.04 (16)C25—C26—C27—C220.3 (7)
P4ii—Ag2—P3—C36−34.59 (17)C23—C22—C27—C260.1 (6)
Ag2ii—Ag2—P3—C36−109.78 (14)P2—C22—C27—C26−173.7 (3)
O3—Ag2—P3—C42−132.21 (16)Ag2—O3—C28—O411.0 (6)
P4ii—Ag2—P3—C4281.16 (16)Ag2—O3—C28—C29−172.5 (3)
Ag2ii—Ag2—P3—C425.97 (14)O4—C28—C29—F4−29.1 (5)
P2i—Ag1—O1—C1−129.4 (3)O3—C28—C29—F4153.9 (4)
P1—Ag1—O1—C165.6 (3)O4—C28—C29—F3−145.2 (4)
Ag1i—Ag1—O1—C1−22.3 (4)O3—C28—C29—F337.9 (5)
P4ii—Ag2—O3—C28−65.3 (3)O4—C28—C29—Cl292.5 (4)
P3—Ag2—O3—C28131.1 (3)O3—C28—C29—Cl2−84.4 (4)
Ag2ii—Ag2—O3—C2819.0 (3)C36—P3—C30—C3560.9 (4)
Ag1—O1—C1—O2−3.4 (6)C42—P3—C30—C35−49.6 (4)
Ag1—O1—C1—C2178.4 (3)Ag2—P3—C30—C35−172.6 (3)
O1—C1—C2—F2−18.6 (7)C36—P3—C30—C31−118.2 (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—C33−0.5 (6)
O1—C1—C2—F188.6 (6)C31—C32—C33—C340.2 (7)
O2—C1—C2—F1−89.8 (6)C32—C33—C34—C350.2 (7)
O1—C1—C2—Cl1'87.2 (5)C31—C30—C35—C34−0.1 (6)
O2—C1—C2—Cl1'−91.3 (5)P3—C30—C35—C34−179.2 (3)
O1—C1—C2—Cl1−152.1 (4)C33—C34—C35—C30−0.3 (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—C37−113.2 (4)
Ag1—P1—C3—C4−76.9 (4)C30—P3—C36—C41−169.0 (3)
C9—P1—C3—C8−33.6 (4)C42—P3—C36—C41−58.0 (4)
C15—P1—C3—C8−142.2 (4)Ag2—P3—C36—C4160.3 (4)
Ag1—P1—C3—C899.1 (4)C41—C36—C37—C38−0.5 (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—C6−0.3 (7)C37—C38—C39—C400.1 (7)
C4—C5—C6—C7−0.6 (7)C38—C39—C40—C41−0.7 (7)
C5—C6—C7—C80.2 (7)C39—C40—C41—C360.7 (7)
C6—C7—C8—C31.0 (7)C37—C36—C41—C40−0.1 (7)
C4—C3—C8—C7−1.9 (7)P3—C36—C41—C40−174.0 (4)
P1—C3—C8—C7−177.8 (3)C43—P4—C42—P363.2 (3)
C3—P1—C9—C14142.2 (3)C49—P4—C42—P3172.6 (2)
C15—P1—C9—C14−110.6 (4)Ag2ii—P4—C42—P3−68.2 (2)
Ag1—P1—C9—C1412.6 (4)C30—P3—C42—P4−97.8 (2)
C3—P1—C9—C10−40.2 (4)C36—P3—C42—P4151.5 (2)
C15—P1—C9—C1067.0 (4)Ag2—P3—C42—P431.2 (2)
Ag1—P1—C9—C10−169.8 (3)C49—P4—C43—C44−54.0 (4)
C14—C9—C10—C11−1.5 (6)C42—P4—C43—C4455.8 (4)
P1—C9—C10—C11−179.1 (3)Ag2ii—P4—C43—C44−178.9 (3)
C9—C10—C11—C121.3 (7)C49—P4—C43—C48129.3 (3)
C10—C11—C12—C130.2 (7)C42—P4—C43—C48−121.0 (3)
C11—C12—C13—C14−1.5 (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—C45−176.0 (3)
P1—C9—C14—C13177.9 (3)C43—C44—C45—C461.1 (7)
C9—P1—C15—P262.7 (3)C44—C45—C46—C47−1.9 (7)
C3—P1—C15—P2172.8 (2)C45—C46—C47—C480.7 (7)
Ag1—P1—C15—P2−66.1 (2)C46—C47—C48—C431.2 (7)
C16—P2—C15—P1−99.2 (2)C44—C43—C48—C47−2.0 (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—C17−34.4 (4)Ag2ii—P4—C49—C50−72.7 (4)
Ag1i—P2—C16—C17−163.2 (3)C43—P4—C49—C54−31.0 (4)
C22—P2—C16—C21−95.5 (4)C42—P4—C49—C54−138.7 (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—C18−0.9 (7)P4—C49—C50—C51174.9 (3)
P2—C16—C17—C18−171.5 (3)C49—C50—C51—C52−0.5 (7)
C16—C17—C18—C191.8 (7)C50—C51—C52—C53−1.0 (7)
C17—C18—C19—C20−1.1 (7)C51—C52—C53—C541.7 (7)
C18—C19—C20—C21−0.5 (8)C52—C53—C54—C49−1.0 (7)
C17—C16—C21—C20−0.7 (7)C50—C49—C54—C53−0.5 (7)
P2—C16—C21—C20170.4 (4)P4—C49—C54—C53−174.1 (4)

Symmetry codes: (i) −x+1, −y+2, −z+2; (ii) −x+1, −y+1, −z+1.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LH2610).

References

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