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Acta Crystallogr Sect E Struct Rep Online. 2009 August 1; 65(Pt 8): m914.
Published online 2009 July 11. doi:  10.1107/S1600536809025513
PMCID: PMC2977105

Bis[μ-1,2-bis­(diphenyl­phosphino)ethane-κ2 P:P′]digold(I)(AuAu) bis­(trifluoro­methane­sulfonate) acetonitrile disolvate

Abstract

The title compound, [Au2(C26H24P2)2](CF3SO3)2·2CH3CN, comprises a cyclic cation with a short intra­molecular aurophilic inter­action of 2.9220 (3) Å. The trifluoro­methane­sulfonate anions and acetonitrile solvent mol­ecules are located in channels formed by the complex cations that run along the crystallographic c axis. Each counter-anion is also engaged in a C—H(...)O contact with one of the methyl­ene H atoms of a 1,2-bis­(diphenyl­phosphino)ethane (dppe) ligand; another C—H(...)O contact involving an aromatic H atom is also observed.

Related literature

For 31P NMR evidence of [Au2(μ-dppe)3]2+, see: Al-Baker et al. (1985 [triangle]). For [Au2(μ-dppm)2]2+, see: de Jongh et al. (2007 [triangle]). For a related structure, see: Schuh et al. (2001 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-0m914-scheme1.jpg

Experimental

Crystal data

  • [Au2(C26H24P2)2](CF3SO3)2·2C2H3N
  • M r = 1571.0
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-0m914-efi1.jpg
  • a = 11.7888 (9) Å
  • b = 36.998 (3) Å
  • c = 14.377 (1) Å
  • β = 113.011 (1)°
  • V = 5771.6 (8) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 5.33 mm−1
  • T = 100 K
  • 0.21 × 0.15 × 0.07 mm

Data collection

  • Bruker SMART APEX CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2002 [triangle]) T min = 0.404, T max = 0.686
  • 36089 measured reflections
  • 13385 independent reflections
  • 10742 reflections with I > 2σ(I)
  • R int = 0.048

Refinement

  • R[F 2 > 2σ(F 2)] = 0.042
  • wR(F 2) = 0.095
  • S = 1.01
  • 13385 reflections
  • 723 parameters
  • H-atom parameters constrained
  • Δρmax = 2.35 e Å−3
  • Δρmin = −0.75 e Å−3

Data collection: SMART (Bruker, 2002 [triangle]); cell refinement: SAINT (Bruker, 2003 [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]; Atwood & Barbour, 2003 [triangle]); software used to prepare material for publication: X-SEED.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809025513/im2111sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809025513/im2111Isup2.hkl

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

Acknowledgments

We would like to thank the National Research Foundation (NRF) of South Africa for financial support.

supplementary crystallographic information

Comment

Ditopic phosphines can form cyclic cations with gold(I) and especially dppm [bis(diphenylphosphino)methane] readily yields the [Au2(µ-dppm)2]2+ cation (de Jongh et al., 2007; and references cited therein). However, the tendency of dppe [1,2-bis(diphenylphosphino)ethane] to form cyclic cations is less apparent than that of dppm since only one structural report of a bis(methanol) solvate, [Au2(µ-dppe)2](CF3SO3)2.CH3OH, has been published (Schuh et al., 2001). The two solvates, however are not isomorphous with (I) being monoclinic and the methanol solvate triclinic.

Compound (I) crystallizes as an asymmetric cation with the trifluoromethanesulfonate anions forming two sets of channels running parallel to the crystallographic a axis (for the anion containing S1) and c axis (for the anion containing S2), respectively. The acetonitrile containing N2 is also found in the former channels while another solvent is embedded between the cations.

Compared to the other example of a crystallographically characterized [Au2(µ-dppe)2]2+ cation in literature, (I) (Figure 1) exhibits a shorter aurophilic interaction and slightly wider P1—Au1···Au2—P2 and P3—Au1···Au2—P4 torsion angles [2.9220 (3) Å, -47.11 (5) and -46.89 (5)° in (I) compared to 2.959 (1) Å, -43.8 (1) and -45.0 (1)°, in the example of Schuh et al.]. The angles at the gold centres in (I) are bent significantly from the linear ideal [P1—Au1—P3 171.77 (5)° and P2—Au2—P4 177.10 (5)°] due to the attractive aurophilic interaction. Other geometric parameters between both structures agree very closely and differences would likely be caused by lattice effects. Another noteworthy feature of (I) is the well defined trifluoromethanesulfonate anions and acetonitrile solvent molecules that do not exhibit disorder despite the fact that the thermal displacement ellipsoids of the acetonitrile containing N1 show higher mobility. Disorder of one trifluoromethanesulfonate anion and methanol molecule each was observed in the crystal structure of the bis(methanol) solvate which may have been enhanced by the higher temperature [223 (2) K] at which data were collected.

The title compound (I) was obtained as the exclusive product in an unsuccessful attempt to structurally characterize the [Au2(µ-dppe)3]2+ cation that has been previously detected by 31P NMR spectroscopy (Al-Baker et al., 1985) and its presence in the mother liquor of (I) can therefore not be completely ruled out.

Experimental

The ditopic phosphine dppe (184 mg, 0.46 mmol) was suspended in 20 ml of acetonitrile, sodium trifluoromethanesulfonate (53 mg, 0.31 mmol) was added and the suspension stirred briefly. [AuCl(tht)] (99 mg, 0.31 mmol; tht = tetrahydrothiophene) and few NaCl crystals (to seed precipitation) were subsequently added. After 1 h the precipitated solids were filtered off, the filtrate was reduced to ca 5 ml and layered with diethyl ether. Colourless blocks of (I) crystallized at 258 K. No other species could be identified in the crystalline phase.

Refinement

All H atoms were positioned geometrically (C—H = 0.95, 0.99 and 0.98 Å for CH, CH2 and CH3 groups, respectively) and constrained to ride on their parent atoms; Uiso(H) values were set at 1.2 times Ueq(C) for CH and CH2 groups and 1.5 times Ueq(C) for CH3 groups.

The maximum residual electron density of 2.35 e Å-3 is located 0.85 Å next to Au1.

Figures

Fig. 1.
The asymmetric unit of (I), ellipsoids are drawn at the 50% probability level.

Crystal data

[Au2(C26H24P2)2](CF3SO3)2·2C2H3NF(000) = 3072
Mr = 1571.0Dx = 1.808 Mg m3
Monoclinic, P21/cMelting point: 528 K
Hall symbol: -P 2ybcMo Kα radiation, λ = 0.71073 Å
a = 11.7888 (9) ÅCell parameters from 6846 reflections
b = 36.998 (3) Åθ = 2.2–27.1°
c = 14.377 (1) ŵ = 5.33 mm1
β = 113.011 (1)°T = 100 K
V = 5771.6 (8) Å3Block, colourless
Z = 40.21 × 0.15 × 0.07 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer13385 independent reflections
Radiation source: fine-focus sealed tube10742 reflections with I > 2σ(I)
graphiteRint = 0.048
ω scansθmax = 28.2°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Bruker, 2002)h = −15→14
Tmin = 0.404, Tmax = 0.686k = −49→36
36089 measured reflectionsl = −19→19

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.042Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.095H-atom parameters constrained
S = 1.01w = 1/[σ2(Fo2) + (0.0437P)2] where P = (Fo2 + 2Fc2)/3
13385 reflections(Δ/σ)max = 0.002
723 parametersΔρmax = 2.35 e Å3
0 restraintsΔρmin = −0.75 e Å3

Special details

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.
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > 2σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

xyzUiso*/Ueq
Au10.623479 (18)0.134499 (5)0.336490 (15)0.01447 (6)
S10.51439 (13)0.41844 (4)0.19532 (10)0.0215 (3)
P10.54886 (12)0.18698 (4)0.24655 (10)0.0140 (3)
F10.7019 (3)0.38763 (10)0.3408 (3)0.0412 (9)
O10.5380 (4)0.39408 (11)0.1268 (3)0.0321 (10)
N10.0693 (7)0.4616 (3)0.4339 (7)0.111 (4)
C10.6633 (6)0.42044 (17)0.3017 (5)0.0338 (15)
Au20.415549 (18)0.128908 (5)0.398184 (15)0.01447 (6)
S20.05080 (14)0.32922 (4)0.64951 (11)0.0270 (3)
P20.43840 (12)0.18914 (4)0.44274 (10)0.0137 (3)
F20.7494 (4)0.43370 (12)0.2719 (3)0.0576 (12)
O20.4945 (4)0.45535 (11)0.1614 (3)0.0310 (10)
N20.1128 (5)0.3048 (2)0.3405 (5)0.0543 (18)
C20.0292 (5)0.34533 (17)0.7605 (5)0.0288 (14)
P30.71663 (12)0.08150 (4)0.41409 (10)0.0147 (3)
F30.6598 (4)0.44111 (12)0.3755 (3)0.0591 (13)
O30.4330 (4)0.40469 (12)0.2393 (3)0.0341 (10)
C3−0.0048 (7)0.4312 (2)0.5593 (6)0.0466 (18)
H3A−0.07080.41430.52190.070*
H3B−0.03610.44910.59370.070*
H3C0.06390.41790.60940.070*
P40.39442 (12)0.06958 (4)0.34652 (10)0.0150 (3)
F40.1308 (3)0.34219 (12)0.8437 (3)0.0470 (11)
O40.1513 (4)0.35096 (12)0.6475 (3)0.0370 (11)
C40.0371 (7)0.4493 (2)0.4906 (6)0.055 (2)
F5−0.0018 (4)0.38046 (11)0.7517 (3)0.0530 (12)
O5−0.0660 (4)0.33678 (14)0.5692 (3)0.0416 (12)
C50.0301 (8)0.3640 (2)0.3840 (6)0.058 (2)
H5A0.09730.38150.41150.088*
H5B−0.00450.35890.43440.088*
H5C−0.03430.37390.32290.088*
F6−0.0600 (3)0.32773 (11)0.7752 (3)0.0432 (10)
O60.0822 (4)0.29207 (12)0.6734 (4)0.0435 (12)
C60.0770 (7)0.3311 (2)0.3592 (5)0.0416 (17)
C110.3965 (4)0.20169 (14)0.2369 (4)0.0154 (11)
H11A0.36590.21990.18230.018*
H11B0.34040.18060.21520.018*
C120.3855 (5)0.21770 (14)0.3307 (4)0.0172 (11)
H12A0.29790.22380.31380.021*
H12B0.43280.24060.34760.021*
C210.6443 (5)0.05786 (14)0.4879 (4)0.0160 (11)
H21A0.70090.03830.52560.019*
H21B0.63870.07510.53860.019*
C220.5162 (5)0.04105 (13)0.4334 (4)0.0176 (11)
H22A0.48790.03200.48560.021*
H22B0.52530.01980.39510.021*
C1110.5323 (5)0.17899 (13)0.1181 (4)0.0146 (10)
C1120.4219 (5)0.18370 (14)0.0346 (4)0.0170 (11)
H1120.35100.19210.04390.020*
C1130.4150 (5)0.17621 (15)−0.0620 (4)0.0231 (12)
H1130.34000.1800−0.11880.028*
C1140.5184 (5)0.16318 (15)−0.0755 (4)0.0237 (12)
H1140.51300.1571−0.14130.028*
C1150.6284 (5)0.15913 (15)0.0063 (4)0.0240 (12)
H1150.69970.1513−0.00330.029*
C1160.6350 (5)0.16644 (14)0.1019 (4)0.0203 (12)
H1160.71070.16290.15810.024*
C1210.6486 (5)0.22545 (14)0.2910 (4)0.0157 (11)
C1220.7689 (5)0.22112 (17)0.3589 (4)0.0247 (13)
H1220.80060.19770.38140.030*
C1230.8436 (6)0.25158 (19)0.3942 (5)0.0362 (16)
H1230.92630.24880.44110.043*
C1240.7982 (6)0.28533 (18)0.3617 (5)0.0340 (16)
H1240.84960.30590.38650.041*
C1250.6787 (6)0.28986 (16)0.2932 (5)0.0299 (14)
H1250.64810.31340.27070.036*
C1260.6040 (5)0.26026 (15)0.2576 (4)0.0211 (12)
H1260.52170.26340.21010.025*
C2110.3496 (4)0.20220 (13)0.5156 (4)0.0132 (10)
C2120.3608 (5)0.18048 (14)0.5987 (4)0.0175 (11)
H2120.41410.16010.61500.021*
C2130.2948 (5)0.18857 (16)0.6568 (4)0.0235 (13)
H2130.30470.17420.71430.028*
C2140.2145 (5)0.21744 (16)0.6315 (4)0.0237 (13)
H2140.16780.22260.67090.028*
C2150.2014 (5)0.23887 (15)0.5494 (4)0.0231 (12)
H2150.14680.25890.53320.028*
C2160.2677 (5)0.23123 (14)0.4904 (4)0.0176 (11)
H2160.25730.24570.43310.021*
C2210.5969 (5)0.20160 (13)0.5168 (4)0.0147 (11)
C2220.6842 (5)0.17419 (14)0.5606 (4)0.0178 (11)
H2220.65960.14960.55210.021*
C2230.8067 (5)0.18318 (16)0.6163 (4)0.0224 (12)
H2230.86590.16470.64560.027*
C2240.8423 (5)0.21888 (16)0.6291 (4)0.0233 (12)
H2240.92610.22490.66700.028*
C2250.7564 (5)0.24615 (15)0.5867 (4)0.0224 (12)
H2250.78160.27070.59580.027*
C2260.6345 (5)0.23751 (13)0.5316 (4)0.0166 (11)
H2260.57590.25620.50360.020*
C3110.8709 (5)0.09196 (14)0.5052 (4)0.0171 (11)
C3120.9202 (5)0.07739 (15)0.6013 (4)0.0237 (12)
H3120.87200.06160.62320.028*
C3131.0394 (5)0.08574 (16)0.6656 (4)0.0246 (13)
H3131.07260.07530.73120.029*
C3141.1105 (5)0.10878 (16)0.6365 (4)0.0281 (14)
H3141.19260.11420.68110.034*
C3151.0600 (6)0.12436 (16)0.5395 (5)0.0314 (15)
H3151.10770.14060.51830.038*
C3160.9410 (5)0.11595 (15)0.4754 (4)0.0236 (12)
H3160.90660.12670.41030.028*
C3210.7306 (5)0.04977 (14)0.3231 (4)0.0184 (11)
C3220.7267 (5)0.01260 (15)0.3364 (4)0.0206 (12)
H3220.71890.00340.39530.025*
C3230.7340 (5)−0.01093 (16)0.2645 (5)0.0310 (15)
H3230.7294−0.03630.27290.037*
C3240.7480 (5)0.00253 (18)0.1808 (5)0.0328 (15)
H3240.7550−0.01370.13200.039*
C3250.7521 (5)0.03941 (17)0.1665 (4)0.0294 (14)
H3250.76190.04840.10820.035*
C3260.7420 (5)0.06317 (15)0.2373 (4)0.0227 (12)
H3260.74290.08850.22700.027*
C4110.2566 (5)0.04865 (14)0.3496 (4)0.0169 (11)
C4120.2230 (5)0.05834 (15)0.4281 (4)0.0231 (12)
H4120.26960.07600.47570.028*
C4130.1218 (5)0.04255 (16)0.4376 (5)0.0269 (13)
H4130.09960.04900.49220.032*
C4140.0529 (5)0.01721 (16)0.3673 (4)0.0265 (13)
H414−0.01740.00660.37310.032*
C4150.0858 (5)0.00731 (16)0.2890 (4)0.0266 (13)
H4150.0388−0.01030.24130.032*
C4160.1883 (5)0.02315 (15)0.2798 (4)0.0236 (12)
H4160.21120.01640.22580.028*
C4210.3955 (4)0.06367 (13)0.2221 (4)0.0151 (11)
C4220.3721 (5)0.09313 (15)0.1579 (4)0.0216 (12)
H4220.35190.11580.17820.026*
C4230.3780 (5)0.08951 (16)0.0631 (4)0.0282 (14)
H4230.36010.10960.01860.034*
C4240.4097 (5)0.05691 (16)0.0344 (4)0.0277 (14)
H4240.41720.0548−0.02880.033*
C4250.4304 (5)0.02744 (16)0.0964 (4)0.0264 (13)
H4250.44910.00480.07460.032*
C4260.4246 (5)0.03023 (14)0.1899 (4)0.0201 (12)
H4260.44010.00970.23260.024*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Au10.01467 (11)0.01186 (10)0.01630 (11)0.00198 (7)0.00542 (8)0.00180 (8)
S10.0256 (8)0.0168 (7)0.0209 (7)−0.0008 (5)0.0078 (6)0.0022 (6)
P10.0143 (7)0.0131 (6)0.0138 (6)0.0013 (5)0.0046 (6)0.0010 (5)
F10.039 (2)0.031 (2)0.046 (2)0.0108 (17)0.0080 (19)0.0172 (18)
O10.049 (3)0.020 (2)0.031 (2)−0.0057 (19)0.019 (2)−0.0058 (19)
N10.067 (6)0.153 (9)0.103 (7)−0.006 (6)0.023 (5)0.088 (7)
C10.035 (4)0.027 (3)0.032 (4)0.000 (3)0.006 (3)0.006 (3)
Au20.01510 (11)0.01046 (10)0.01807 (11)−0.00068 (7)0.00673 (8)−0.00238 (8)
S20.0228 (8)0.0291 (8)0.0316 (8)0.0023 (6)0.0132 (7)−0.0049 (7)
P20.0140 (7)0.0121 (6)0.0146 (6)−0.0006 (5)0.0050 (6)−0.0010 (5)
F20.036 (2)0.057 (3)0.068 (3)−0.012 (2)0.008 (2)0.023 (2)
O20.040 (3)0.019 (2)0.029 (2)0.0025 (18)0.008 (2)0.0015 (18)
N20.032 (4)0.064 (5)0.055 (4)0.000 (3)0.004 (3)−0.007 (4)
C20.021 (3)0.032 (4)0.029 (3)0.000 (3)0.005 (3)−0.002 (3)
P30.0134 (7)0.0118 (6)0.0178 (7)0.0015 (5)0.0047 (6)0.0009 (5)
F30.075 (3)0.052 (3)0.027 (2)0.009 (2)−0.006 (2)−0.012 (2)
O30.031 (2)0.034 (3)0.041 (3)0.0042 (19)0.017 (2)0.011 (2)
C30.052 (5)0.041 (4)0.055 (5)−0.006 (3)0.030 (4)−0.005 (4)
P40.0146 (7)0.0111 (6)0.0192 (7)−0.0010 (5)0.0066 (6)−0.0024 (5)
F40.027 (2)0.077 (3)0.027 (2)−0.003 (2)−0.0003 (17)−0.001 (2)
O40.025 (2)0.042 (3)0.047 (3)0.001 (2)0.017 (2)0.007 (2)
C40.035 (4)0.065 (6)0.058 (5)0.004 (4)0.011 (4)0.026 (4)
F50.077 (3)0.036 (2)0.053 (3)0.017 (2)0.033 (3)−0.004 (2)
O50.028 (3)0.066 (4)0.025 (2)−0.003 (2)0.005 (2)−0.012 (2)
C50.087 (7)0.045 (5)0.054 (5)−0.002 (4)0.040 (5)0.007 (4)
F60.026 (2)0.070 (3)0.040 (2)−0.0067 (19)0.0208 (18)−0.004 (2)
O60.049 (3)0.026 (2)0.064 (3)0.006 (2)0.032 (3)−0.006 (2)
C60.036 (4)0.049 (5)0.040 (4)−0.010 (3)0.015 (3)−0.002 (4)
C110.013 (3)0.016 (3)0.014 (2)0.002 (2)0.002 (2)0.002 (2)
C120.016 (3)0.016 (3)0.017 (3)0.003 (2)0.004 (2)−0.005 (2)
C210.015 (3)0.016 (3)0.017 (3)0.002 (2)0.005 (2)0.003 (2)
C220.021 (3)0.010 (2)0.023 (3)−0.002 (2)0.009 (2)−0.001 (2)
C1110.020 (3)0.011 (2)0.011 (2)−0.002 (2)0.005 (2)0.001 (2)
C1120.016 (3)0.015 (3)0.019 (3)0.002 (2)0.005 (2)0.001 (2)
C1130.022 (3)0.028 (3)0.014 (3)0.001 (2)0.001 (2)−0.002 (2)
C1140.032 (3)0.022 (3)0.020 (3)−0.004 (2)0.013 (3)−0.004 (2)
C1150.021 (3)0.024 (3)0.029 (3)0.000 (2)0.012 (3)−0.002 (3)
C1160.017 (3)0.022 (3)0.023 (3)0.002 (2)0.009 (2)−0.001 (2)
C1210.018 (3)0.015 (3)0.015 (3)−0.002 (2)0.007 (2)−0.002 (2)
C1220.016 (3)0.034 (3)0.023 (3)−0.001 (2)0.006 (2)0.001 (3)
C1230.023 (3)0.053 (5)0.026 (3)−0.020 (3)0.003 (3)−0.004 (3)
C1240.045 (4)0.032 (4)0.031 (3)−0.021 (3)0.022 (3)−0.016 (3)
C1250.047 (4)0.017 (3)0.033 (3)0.000 (3)0.024 (3)−0.006 (3)
C1260.023 (3)0.019 (3)0.021 (3)0.002 (2)0.009 (2)0.001 (2)
C2110.013 (3)0.013 (2)0.013 (2)−0.0059 (19)0.005 (2)−0.006 (2)
C2120.016 (3)0.017 (3)0.015 (3)−0.002 (2)0.001 (2)−0.003 (2)
C2130.023 (3)0.025 (3)0.021 (3)−0.011 (2)0.008 (3)−0.004 (2)
C2140.019 (3)0.033 (3)0.026 (3)−0.013 (2)0.015 (3)−0.011 (3)
C2150.017 (3)0.024 (3)0.029 (3)−0.002 (2)0.009 (3)−0.012 (3)
C2160.018 (3)0.017 (3)0.017 (3)0.000 (2)0.006 (2)−0.003 (2)
C2210.014 (3)0.014 (3)0.015 (2)−0.002 (2)0.004 (2)−0.003 (2)
C2220.018 (3)0.016 (3)0.017 (3)0.000 (2)0.005 (2)−0.002 (2)
C2230.018 (3)0.026 (3)0.020 (3)0.006 (2)0.003 (2)0.001 (2)
C2240.019 (3)0.031 (3)0.018 (3)−0.002 (2)0.006 (2)−0.002 (2)
C2250.022 (3)0.023 (3)0.021 (3)−0.008 (2)0.007 (3)−0.007 (2)
C2260.019 (3)0.012 (3)0.020 (3)0.001 (2)0.008 (2)0.000 (2)
C3110.010 (3)0.018 (3)0.020 (3)0.005 (2)0.002 (2)−0.003 (2)
C3120.022 (3)0.017 (3)0.032 (3)0.000 (2)0.011 (3)−0.001 (2)
C3130.022 (3)0.026 (3)0.023 (3)0.005 (2)0.005 (3)0.002 (2)
C3140.017 (3)0.028 (3)0.032 (3)−0.004 (2)0.002 (3)−0.011 (3)
C3150.028 (3)0.026 (3)0.042 (4)−0.008 (3)0.015 (3)−0.001 (3)
C3160.019 (3)0.026 (3)0.023 (3)0.002 (2)0.005 (2)0.004 (2)
C3210.014 (3)0.018 (3)0.019 (3)0.004 (2)0.003 (2)0.000 (2)
C3220.013 (3)0.022 (3)0.030 (3)0.004 (2)0.012 (2)0.002 (2)
C3230.018 (3)0.022 (3)0.049 (4)0.000 (2)0.008 (3)−0.009 (3)
C3240.023 (3)0.042 (4)0.029 (3)−0.001 (3)0.006 (3)−0.020 (3)
C3250.028 (3)0.037 (4)0.025 (3)−0.004 (3)0.013 (3)−0.005 (3)
C3260.022 (3)0.021 (3)0.026 (3)−0.004 (2)0.010 (3)−0.003 (2)
C4110.013 (3)0.012 (3)0.022 (3)−0.002 (2)0.003 (2)0.001 (2)
C4120.024 (3)0.018 (3)0.024 (3)0.000 (2)0.006 (3)−0.005 (2)
C4130.024 (3)0.027 (3)0.033 (3)0.006 (2)0.015 (3)0.003 (3)
C4140.018 (3)0.025 (3)0.036 (3)−0.003 (2)0.009 (3)0.006 (3)
C4150.020 (3)0.023 (3)0.028 (3)−0.009 (2)−0.001 (3)−0.004 (3)
C4160.028 (3)0.019 (3)0.026 (3)−0.003 (2)0.013 (3)−0.004 (2)
C4210.011 (3)0.013 (2)0.017 (3)−0.0030 (19)0.001 (2)−0.004 (2)
C4220.021 (3)0.020 (3)0.020 (3)−0.001 (2)0.003 (2)−0.002 (2)
C4230.035 (4)0.025 (3)0.019 (3)−0.008 (3)0.004 (3)−0.003 (2)
C4240.029 (3)0.032 (3)0.022 (3)−0.015 (3)0.009 (3)−0.009 (3)
C4250.022 (3)0.026 (3)0.029 (3)−0.001 (2)0.008 (3)−0.008 (3)
C4260.020 (3)0.013 (3)0.028 (3)0.002 (2)0.009 (2)0.000 (2)

Geometric parameters (Å, °)

Au1—P12.3079 (13)C125—C1261.373 (8)
Au1—P32.3105 (13)C125—H1250.9500
Au1—Au22.9220 (3)C126—H1260.9500
S1—O31.433 (4)C211—C2161.394 (7)
S1—O21.438 (4)C211—C2121.402 (7)
S1—O11.440 (4)C212—C2131.379 (7)
S1—C11.824 (6)C212—H2120.9500
P1—C1211.797 (5)C213—C2141.379 (8)
P1—C1111.804 (5)C213—H2130.9500
P1—C111.829 (5)C214—C2151.380 (8)
F1—C11.340 (7)C214—H2140.9500
N1—C41.121 (10)C215—C2161.390 (7)
C1—F31.323 (7)C215—H2150.9500
C1—F21.338 (7)C216—H2160.9500
Au2—P42.2993 (13)C221—C2261.390 (7)
Au2—P22.3052 (13)C221—C2221.407 (7)
S2—O61.430 (5)C222—C2231.390 (7)
S2—O51.437 (4)C222—H2220.9500
S2—O41.442 (4)C223—C2241.376 (8)
S2—C21.813 (6)C223—H2230.9500
P2—C2211.811 (5)C224—C2251.390 (8)
P2—C2111.812 (5)C224—H2240.9500
P2—C121.820 (5)C225—C2261.380 (7)
N2—C61.134 (9)C225—H2250.9500
C2—F61.322 (7)C226—H2260.9500
C2—F41.326 (6)C311—C3121.382 (7)
C2—F51.343 (7)C311—C3161.389 (7)
P3—C3211.812 (5)C312—C3131.382 (8)
P3—C3111.819 (5)C312—H3120.9500
P3—C211.823 (5)C313—C3141.371 (8)
C3—C41.430 (10)C313—H3130.9500
C3—H3A0.9800C314—C3151.408 (8)
C3—H3B0.9800C314—H3140.9500
C3—H3C0.9800C315—C3161.380 (8)
P4—C4211.807 (5)C315—H3150.9500
P4—C4111.816 (5)C316—H3160.9500
P4—C221.826 (5)C321—C3261.384 (7)
C5—C61.437 (10)C321—C3221.392 (7)
C5—H5A0.9800C322—C3231.380 (8)
C5—H5B0.9800C322—H3220.9500
C5—H5C0.9800C323—C3241.371 (9)
C11—C121.525 (7)C323—H3230.9500
C11—H11A0.9900C324—C3251.383 (9)
C11—H11B0.9900C324—H3240.9500
C12—H12A0.9900C325—C3261.385 (8)
C12—H12B0.9900C325—H3250.9500
C21—C221.536 (7)C326—H3260.9500
C21—H21A0.9900C411—C4121.382 (7)
C21—H21B0.9900C411—C4161.383 (7)
C22—H22A0.9900C412—C4131.382 (8)
C22—H22B0.9900C412—H4120.9500
C111—C1121.394 (7)C413—C4141.385 (8)
C111—C1161.398 (7)C413—H4130.9500
C112—C1131.387 (7)C414—C4151.375 (8)
C112—H1120.9500C414—H4140.9500
C113—C1141.393 (8)C415—C4161.395 (8)
C113—H1130.9500C415—H4150.9500
C114—C1151.377 (7)C416—H4160.9500
C114—H1140.9500C421—C4221.385 (7)
C115—C1161.373 (7)C421—C4261.409 (7)
C115—H1150.9500C422—C4231.397 (7)
C116—H1160.9500C422—H4220.9500
C121—C1221.381 (7)C423—C4241.373 (8)
C121—C1261.403 (7)C423—H4230.9500
C122—C1231.398 (8)C424—C4251.368 (8)
C122—H1220.9500C424—H4240.9500
C123—C1241.367 (9)C425—C4261.377 (7)
C123—H1230.9500C425—H4250.9500
C124—C1251.377 (9)C426—H4260.9500
C124—H1240.9500
P1—Au1—P3171.77 (5)C122—C123—H123119.8
P1—Au1—Au292.77 (3)C123—C124—C125120.6 (6)
P3—Au1—Au295.17 (3)C123—C124—H124119.7
O3—S1—O2116.0 (3)C125—C124—H124119.7
O3—S1—O1114.9 (3)C126—C125—C124119.8 (6)
O2—S1—O1114.3 (2)C126—C125—H125120.1
O3—S1—C1103.7 (3)C124—C125—H125120.1
O2—S1—C1102.8 (3)C125—C126—C121120.3 (5)
O1—S1—C1102.6 (3)C125—C126—H126119.9
C121—P1—C111106.7 (2)C121—C126—H126119.9
C121—P1—C11106.2 (2)C216—C211—C212119.2 (5)
C111—P1—C11105.1 (2)C216—C211—P2123.6 (4)
C121—P1—Au1114.46 (18)C212—C211—P2117.1 (4)
C111—P1—Au1107.50 (17)C213—C212—C211120.3 (5)
C11—P1—Au1116.15 (17)C213—C212—H212119.9
F3—C1—F2108.1 (5)C211—C212—H212119.9
F3—C1—F1107.4 (5)C214—C213—C212120.1 (5)
F2—C1—F1106.9 (5)C214—C213—H213120.0
F3—C1—S1112.0 (5)C212—C213—H213120.0
F2—C1—S1110.4 (4)C213—C214—C215120.4 (5)
F1—C1—S1111.9 (4)C213—C214—H214119.8
P4—Au2—P2177.10 (5)C215—C214—H214119.8
P4—Au2—Au188.13 (3)C214—C215—C216120.3 (5)
P2—Au2—Au189.72 (3)C214—C215—H215119.8
O6—S2—O5117.2 (3)C216—C215—H215119.8
O6—S2—O4113.8 (3)C215—C216—C211119.7 (5)
O5—S2—O4114.3 (3)C215—C216—H216120.1
O6—S2—C2102.5 (3)C211—C216—H216120.1
O5—S2—C2102.9 (3)C226—C221—C222119.1 (5)
O4—S2—C2103.5 (3)C226—C221—P2121.8 (4)
C221—P2—C211106.8 (2)C222—C221—P2119.1 (4)
C221—P2—C12106.9 (2)C223—C222—C221119.9 (5)
C211—P2—C12106.3 (2)C223—C222—H222120.0
C221—P2—Au2113.02 (17)C221—C222—H222120.0
C211—P2—Au2112.79 (16)C224—C223—C222120.0 (5)
C12—P2—Au2110.66 (17)C224—C223—H223120.0
F6—C2—F4107.9 (5)C222—C223—H223120.0
F6—C2—F5106.8 (5)C223—C224—C225120.4 (5)
F4—C2—F5106.7 (5)C223—C224—H224119.8
F6—C2—S2111.9 (4)C225—C224—H224119.8
F4—C2—S2112.1 (4)C226—C225—C224120.0 (5)
F5—C2—S2111.2 (4)C226—C225—H225120.0
C321—P3—C311108.1 (2)C224—C225—H225120.0
C321—P3—C21107.7 (2)C225—C226—C221120.5 (5)
C311—P3—C21104.3 (2)C225—C226—H226119.7
C321—P3—Au1111.19 (17)C221—C226—H226119.7
C311—P3—Au1108.64 (17)C312—C311—C316119.2 (5)
C21—P3—Au1116.49 (17)C312—C311—P3123.2 (4)
C4—C3—H3A109.5C316—C311—P3117.5 (4)
C4—C3—H3B109.5C313—C312—C311120.2 (5)
H3A—C3—H3B109.5C313—C312—H312119.9
C4—C3—H3C109.5C311—C312—H312119.9
H3A—C3—H3C109.5C314—C313—C312121.2 (5)
H3B—C3—H3C109.5C314—C313—H313119.4
C421—P4—C411109.0 (2)C312—C313—H313119.4
C421—P4—C22107.4 (2)C313—C314—C315119.0 (5)
C411—P4—C22102.0 (2)C313—C314—H314120.5
C421—P4—Au2113.18 (17)C315—C314—H314120.5
C411—P4—Au2112.60 (18)C316—C315—C314119.6 (6)
C22—P4—Au2111.96 (17)C316—C315—H315120.2
N1—C4—C3176.0 (11)C314—C315—H315120.2
C6—C5—H5A109.5C315—C316—C311120.7 (5)
C6—C5—H5B109.5C315—C316—H316119.6
H5A—C5—H5B109.5C311—C316—H316119.6
C6—C5—H5C109.5C326—C321—C322119.7 (5)
H5A—C5—H5C109.5C326—C321—P3118.6 (4)
H5B—C5—H5C109.5C322—C321—P3121.6 (4)
N2—C6—C5178.7 (9)C323—C322—C321120.3 (5)
C12—C11—P1118.0 (3)C323—C322—H322119.8
C12—C11—H11A107.8C321—C322—H322119.8
P1—C11—H11A107.8C324—C323—C322119.6 (6)
C12—C11—H11B107.8C324—C323—H323120.2
P1—C11—H11B107.8C322—C323—H323120.2
H11A—C11—H11B107.1C323—C324—C325120.8 (6)
C11—C12—P2116.0 (3)C323—C324—H324119.6
C11—C12—H12A108.3C325—C324—H324119.6
P2—C12—H12A108.3C324—C325—C326119.9 (6)
C11—C12—H12B108.3C324—C325—H325120.0
P2—C12—H12B108.3C326—C325—H325120.0
H12A—C12—H12B107.4C321—C326—C325119.6 (5)
C22—C21—P3119.2 (4)C321—C326—H326120.2
C22—C21—H21A107.5C325—C326—H326120.2
P3—C21—H21A107.5C412—C411—C416119.9 (5)
C22—C21—H21B107.5C412—C411—P4117.0 (4)
P3—C21—H21B107.5C416—C411—P4123.1 (4)
H21A—C21—H21B107.0C411—C412—C413120.3 (5)
C21—C22—P4117.9 (3)C411—C412—H412119.8
C21—C22—H22A107.8C413—C412—H412119.8
P4—C22—H22A107.8C412—C413—C414119.7 (5)
C21—C22—H22B107.8C412—C413—H413120.1
P4—C22—H22B107.8C414—C413—H413120.1
H22A—C22—H22B107.2C415—C414—C413120.4 (5)
C112—C111—C116118.4 (5)C415—C414—H414119.8
C112—C111—P1123.5 (4)C413—C414—H414119.8
C116—C111—P1118.0 (4)C414—C415—C416119.8 (5)
C113—C112—C111120.5 (5)C414—C415—H415120.1
C113—C112—H112119.8C416—C415—H415120.1
C111—C112—H112119.8C411—C416—C415119.9 (5)
C112—C113—C114119.8 (5)C411—C416—H416120.1
C112—C113—H113120.1C415—C416—H416120.1
C114—C113—H113120.1C422—C421—C426118.9 (5)
C115—C114—C113120.1 (5)C422—C421—P4119.2 (4)
C115—C114—H114119.9C426—C421—P4121.9 (4)
C113—C114—H114119.9C421—C422—C423120.1 (5)
C116—C115—C114120.0 (5)C421—C422—H422120.0
C116—C115—H115120.0C423—C422—H422120.0
C114—C115—H115120.0C424—C423—C422120.0 (6)
C115—C116—C111121.1 (5)C424—C423—H423120.0
C115—C116—H116119.4C422—C423—H423120.0
C111—C116—H116119.4C425—C424—C423120.3 (6)
C122—C121—C126119.5 (5)C425—C424—H424119.8
C122—C121—P1120.5 (4)C423—C424—H424119.8
C126—C121—P1120.0 (4)C424—C425—C426120.8 (6)
C121—C122—C123119.3 (6)C424—C425—H425119.6
C121—C122—H122120.3C426—C425—H425119.6
C123—C122—H122120.3C425—C426—C421119.9 (5)
C124—C123—C122120.4 (6)C425—C426—H426120.1
C124—C123—H123119.8C421—C426—H426120.1
Au2—Au1—P1—C121118.83 (19)C12—P2—C211—C212171.0 (4)
Au2—Au1—P1—C111−122.84 (18)Au2—P2—C211—C21249.6 (4)
Au2—Au1—P1—C11−5.49 (18)C216—C211—C212—C213−2.3 (7)
O3—S1—C1—F3−58.3 (5)P2—C211—C212—C213−179.2 (4)
O2—S1—C1—F362.9 (5)C211—C212—C213—C2142.0 (8)
O1—S1—C1—F3−178.2 (4)C212—C213—C214—C215−1.4 (8)
O3—S1—C1—F2−178.7 (4)C213—C214—C215—C2161.0 (8)
O2—S1—C1—F2−57.6 (5)C214—C215—C216—C211−1.3 (8)
O1—S1—C1—F261.4 (5)C212—C211—C216—C2151.9 (7)
O3—S1—C1—F162.3 (5)P2—C211—C216—C215178.6 (4)
O2—S1—C1—F1−176.5 (4)C211—P2—C221—C226−70.3 (5)
O1—S1—C1—F1−57.6 (5)C12—P2—C221—C22643.1 (5)
P1—Au1—Au2—P4130.95 (5)Au2—P2—C221—C226165.1 (4)
P3—Au1—Au2—P4−46.89 (5)C211—P2—C221—C222109.6 (4)
P1—Au1—Au2—P2−47.11 (5)C12—P2—C221—C222−136.9 (4)
P3—Au1—Au2—P2135.05 (5)Au2—P2—C221—C222−15.0 (5)
Au1—Au2—P2—C221−46.58 (18)C226—C221—C222—C223−1.1 (8)
Au1—Au2—P2—C211−167.81 (18)P2—C221—C222—C223179.0 (4)
Au1—Au2—P2—C1273.24 (19)C221—C222—C223—C2240.3 (8)
O6—S2—C2—F6−60.5 (5)C222—C223—C224—C2250.2 (8)
O5—S2—C2—F661.5 (5)C223—C224—C225—C2260.1 (8)
O4—S2—C2—F6−179.1 (4)C224—C225—C226—C221−0.8 (8)
O6—S2—C2—F460.9 (5)C222—C221—C226—C2251.4 (8)
O5—S2—C2—F4−177.0 (4)P2—C221—C226—C225−178.7 (4)
O4—S2—C2—F4−57.7 (5)C321—P3—C311—C312−102.9 (5)
O6—S2—C2—F5−179.8 (4)C21—P3—C311—C31211.5 (5)
O5—S2—C2—F5−57.7 (5)Au1—P3—C311—C312136.3 (4)
O4—S2—C2—F561.6 (5)C321—P3—C311—C31677.4 (5)
Au2—Au1—P3—C321119.99 (19)C21—P3—C311—C316−168.2 (4)
Au2—Au1—P3—C311−121.21 (18)Au1—P3—C311—C316−43.4 (5)
Au2—Au1—P3—C21−3.91 (19)C316—C311—C312—C313−2.1 (8)
Au1—Au2—P4—C421−48.35 (18)P3—C311—C312—C313178.2 (4)
Au1—Au2—P4—C411−172.49 (19)C311—C312—C313—C3140.8 (8)
Au1—Au2—P4—C2273.23 (19)C312—C313—C314—C3150.6 (9)
C121—P1—C11—C12−55.4 (4)C313—C314—C315—C316−0.6 (9)
C111—P1—C11—C12−168.2 (4)C314—C315—C316—C311−0.7 (9)
Au1—P1—C11—C1273.1 (4)C312—C311—C316—C3152.1 (8)
P1—C11—C12—P2−56.9 (5)P3—C311—C316—C315−178.2 (4)
C221—P2—C12—C1194.4 (4)C311—P3—C321—C326−89.9 (5)
C211—P2—C12—C11−151.8 (4)C21—P3—C321—C326158.0 (4)
Au2—P2—C12—C11−29.0 (4)Au1—P3—C321—C32629.3 (5)
C321—P3—C21—C22−58.8 (4)C311—P3—C321—C32291.9 (5)
C311—P3—C21—C22−173.5 (4)C21—P3—C321—C322−20.2 (5)
Au1—P3—C21—C2266.8 (4)Au1—P3—C321—C322−149.0 (4)
P3—C21—C22—P4−51.2 (5)C326—C321—C322—C323−0.1 (8)
C421—P4—C22—C2191.8 (4)P3—C321—C322—C323178.2 (4)
C411—P4—C22—C21−153.6 (4)C321—C322—C323—C3241.5 (8)
Au2—P4—C22—C21−33.0 (4)C322—C323—C324—C325−1.5 (9)
C121—P1—C111—C112−112.8 (5)C323—C324—C325—C3260.0 (9)
C11—P1—C111—C112−0.3 (5)C322—C321—C326—C325−1.4 (8)
Au1—P1—C111—C112124.0 (4)P3—C321—C326—C325−179.7 (4)
C121—P1—C111—C11669.1 (5)C324—C325—C326—C3211.4 (9)
C11—P1—C111—C116−178.5 (4)C421—P4—C411—C412−163.5 (4)
Au1—P1—C111—C116−54.2 (4)C22—P4—C411—C41283.2 (5)
C116—C111—C112—C113−0.3 (8)Au2—P4—C411—C412−37.0 (5)
P1—C111—C112—C113−178.4 (4)C421—P4—C411—C41618.7 (5)
C111—C112—C113—C1141.3 (8)C22—P4—C411—C416−94.7 (5)
C112—C113—C114—C115−2.6 (9)Au2—P4—C411—C416145.1 (4)
C113—C114—C115—C1162.8 (9)C416—C411—C412—C4130.3 (8)
C114—C115—C116—C111−1.8 (8)P4—C411—C412—C413−177.6 (4)
C112—C111—C116—C1150.5 (8)C411—C412—C413—C414−0.8 (9)
P1—C111—C116—C115178.7 (4)C412—C413—C414—C4151.0 (9)
C111—P1—C121—C122−106.2 (4)C413—C414—C415—C416−0.6 (9)
C11—P1—C121—C122142.1 (4)C412—C411—C416—C4150.0 (8)
Au1—P1—C121—C12212.6 (5)P4—C411—C416—C415177.8 (4)
C111—P1—C121—C12674.7 (5)C414—C415—C416—C4110.1 (9)
C11—P1—C121—C126−37.1 (5)C411—P4—C421—C422107.3 (4)
Au1—P1—C121—C126−166.5 (4)C22—P4—C421—C422−142.9 (4)
C126—C121—C122—C1230.8 (8)Au2—P4—C421—C422−18.8 (5)
P1—C121—C122—C123−178.3 (4)C411—P4—C421—C426−75.3 (5)
C121—C122—C123—C124−0.2 (9)C22—P4—C421—C42634.5 (5)
C122—C123—C124—C125−0.4 (9)Au2—P4—C421—C426158.6 (4)
C123—C124—C125—C1260.3 (9)C426—C421—C422—C423−0.3 (8)
C124—C125—C126—C1210.3 (8)P4—C421—C422—C423177.1 (4)
C122—C121—C126—C125−0.9 (8)C421—C422—C423—C424−1.4 (8)
P1—C121—C126—C125178.3 (4)C422—C423—C424—C4252.8 (9)
C221—P2—C211—C216108.1 (4)C423—C424—C425—C426−2.5 (9)
C12—P2—C211—C216−5.8 (5)C424—C425—C426—C4210.7 (8)
Au2—P2—C211—C216−127.2 (4)C422—C421—C426—C4250.7 (8)
C221—P2—C211—C212−75.2 (4)P4—C421—C426—C425−176.7 (4)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C212—H212···O1i0.952.453.387 (7)171
C21—H21B···O1i0.992.343.268 (7)155
C11—H11B···O4ii0.992.363.301 (7)158

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: IM2111).

References

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