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Acta Crystallogr Sect E Struct Rep Online. 2010 April 1; 66(Pt 4): m450.
Published online 2010 March 27. doi:  10.1107/S1600536810010445
PMCID: PMC2983779

[(Z)-O-Methyl N-(3-chloro­phen­yl)thio­carbamato-κS](tricyclo­hexyl­phosphine-κP)gold(I)

Abstract

Two independent mol­ecules comprise the asymmetric unit of the title compound, [Au(C8H7ClNOS)(C18H33P)], which differ in the relative orientations of each of the cyclo­hexyl groups as well as the benzene ring. In each mol­ecule, the Au atom is coordinated within a S,P-donor set that defines a slightly distorted linear geometry [S—Au—P = 175.10 (5) and 177.26 (5)° for the two mol­ecules], with the distortion due in part to the close intra­molecular approach of the O atom [Au(...)O contacts = 3.054 (4) and 3.013 (4) Å, respectively, for the two mol­ecules].

Related literature

For the structural systematics and luminescence properties of phosphinegold(I) carbonimidothio­ates, see: Ho et al. (2006 [triangle]); Ho & Tiekink (2007 [triangle]); Kuan et al. (2008 [triangle]). For the synthesis, see: Hall et al. (1993 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-0m450-scheme1.jpg

Experimental

Crystal data

  • [Au(C8H7ClNOS)(C18H33P)]
  • M r = 678.04
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-0m450-efi1.jpg
  • a = 19.1964 (8) Å
  • b = 11.7855 (5) Å
  • c = 26.0594 (11) Å
  • β = 107.328 (1)°
  • V = 5628.1 (4) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 5.47 mm−1
  • T = 223 K
  • 0.32 × 0.09 × 0.08 mm

Data collection

  • Bruker SMART CCD diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2000 [triangle]) T min = 0.120, T max = 1.000
  • 39394 measured reflections
  • 12920 independent reflections
  • 9743 reflections with I > 2σ(I)
  • R int = 0.052

Refinement

  • R[F 2 > 2σ(F 2)] = 0.036
  • wR(F 2) = 0.103
  • S = 1.05
  • 12920 reflections
  • 579 parameters
  • H-atom parameters constrained
  • Δρmax = 0.90 e Å−3
  • Δρmin = −1.26 e Å−3

Data collection: SMART (Bruker, 2000 [triangle]); cell refinement: SAINT (Bruker, 2000 [triangle]); data reduction: SAINT; program(s) used to solve structure: PATTY in DIRDIF92 (Beurskens et al., 1992 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: ORTEP-3 (Farrugia, 1997 [triangle]), DIAMOND (Brandenburg, 2006 [triangle]) and Qmol (Gans & Shalloway, 2001 [triangle]); software used to prepare material for publication: publCIF (Westrip, 2010 [triangle]).

Table 1
Selected bond lengths (Å)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810010445/pv2267sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810010445/pv2267Isup2.hkl

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

Acknowledgments

The National University of Singapore (grant No. R-143–000-213–112) is thanked for support.

supplementary crystallographic information

Comment

Molecules of the type R3PAu[SC(OR')═NR''], for R, R' and R'' = alkyl and aryl, attract interest in terms of crystal engineering and luminescence studies (Ho et al. 2006; Ho & Tiekink, 2007; Kuan et al., 2008). It was in this context that the synthesis and characterisation of the title compound, (I), was investigated.

Two independent molecules, a (Fig. 1) and b (Fig. 2), comprise the asymmetric unit of (I). As seen from the overlay diagram, Fig. 3 (Gans & Shalloway, 2001), the molecules differ in terms of the relative orientations of the cyclohexyl and benzene rings. Each of the gold atoms exist within a SP donor set, Table 1, with small deviations from the ideal linearity ascribed to the close approach of the O atom [Au···O contacts = 3.054 (4) and 3.013 (4) Å for molecules a and b, respectively]. The ligand is coordinating as a thiolate as evidenced by the C–S and C═N bond distances, Table 1. No specific intermolecular interactions are noted in the crystal packing.

Experimental

Compound (I) was prepared following the standard literature procedure from the reaction of Cy3PAuCl and MeOC(═S)N(H)(C6H4Cl-3) in the presence of NaOH (Hall et al., 1993). Crystals were obtained by the slow evaporation of a CH2Cl2/hexane (3/1) solution held at room temperature.

Refinement

The H atoms were geometrically placed (C—H = 0.94-0.99 Å) and refined as riding with Uiso(H) = 1.2-1.5Ueq(C). While high thermal motion is noted for some of the cyclohexyl rings, multiple positions for these could not be resolved in the refinement. The maximum and minimum residual electron density peaks of 0.90 and 1.26 e Å-3, respectively, were located 0.38 Å and 0.87 Å from the C5 and Au1 atoms, respectively.

Figures

Fig. 1.
Molecular structure of the first independent molecule comprising the asymmetric unit in (I) showing atom-labelling scheme (the C4 atom is obscured by Cl1) and displacement ellipsoids at the 35% probability level.
Fig. 2.
Molecular structure of the second independent molecule comprising the asymmetric unit in (I) showing atom-labelling scheme and displacement ellipsoids at the 35% probability level.
Fig. 3.
Overlay diagram showing the different conformations for molecule a (red image) and molecule b (blue image).

Crystal data

[Au(C8H7ClNOS)(C18H33P)]F(000) = 2704
Mr = 678.04Dx = 1.600 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71069 Å
Hall symbol: -P 2ybcCell parameters from 7254 reflections
a = 19.1964 (8) Åθ = 2.2–27.8°
b = 11.7855 (5) ŵ = 5.47 mm1
c = 26.0594 (11) ÅT = 223 K
β = 107.328 (1)°Block, colourless
V = 5628.1 (4) Å30.32 × 0.09 × 0.08 mm
Z = 8

Data collection

Bruker SMART CCD diffractometer12920 independent reflections
Radiation source: fine-focus sealed tube9743 reflections with I > 2σ(I)
graphiteRint = 0.052
ω scansθmax = 27.5°, θmin = 1.1°
Absorption correction: multi-scan (SADABS; Bruker, 2000)h = −24→23
Tmin = 0.120, Tmax = 1.000k = −15→15
39394 measured reflectionsl = −33→23

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)] = 0.036Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.103H-atom parameters constrained
S = 1.05w = 1/[σ2(Fo2) + (0.0443P)2 + 1.5842P] where P = (Fo2 + 2Fc2)/3
12920 reflections(Δ/σ)max = 0.002
579 parametersΔρmax = 0.90 e Å3
0 restraintsΔρmin = −1.26 e Å3

Special details

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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
Au10.033556 (11)0.169486 (16)0.215414 (8)0.02957 (7)
Cl1−0.33553 (9)0.21770 (19)0.02053 (7)0.0666 (5)
S1−0.03791 (8)0.22019 (11)0.13099 (6)0.0395 (4)
P10.10367 (7)0.13548 (10)0.30030 (6)0.0260 (3)
O10.0192 (2)0.0287 (3)0.11442 (15)0.0363 (9)
N1−0.0744 (2)0.0891 (4)0.04332 (18)0.0335 (10)
C1−0.0336 (3)0.1047 (4)0.0904 (2)0.0276 (11)
C2−0.1303 (3)0.1714 (4)0.0221 (2)0.0320 (12)
C3−0.1985 (3)0.1575 (5)0.0297 (2)0.0362 (13)
H3−0.20790.09430.04860.043*
C4−0.2516 (3)0.2367 (6)0.0095 (2)0.0418 (15)
C5−0.2408 (3)0.3277 (5)−0.0194 (3)0.0474 (16)
H5−0.27820.3811−0.03280.057*
C6−0.1747 (4)0.3401 (5)−0.0285 (3)0.0535 (18)
H6−0.16710.4019−0.04890.064*
C7−0.1187 (3)0.2630 (5)−0.0081 (2)0.0429 (15)
H7−0.07350.2725−0.01460.051*
C80.0245 (4)−0.0697 (5)0.0832 (3)0.0500 (17)
H8A−0.0213−0.11090.07390.075*
H8B0.0634−0.11850.10400.075*
H8C0.0350−0.04620.05060.075*
C90.1636 (3)0.0117 (4)0.3036 (2)0.0373 (13)
H90.19030.02860.27740.045*
C100.2232 (4)−0.0090 (6)0.3564 (3)0.0561 (18)
H10A0.25210.06040.36680.067*
H10B0.2004−0.02580.38460.067*
C110.2734 (4)−0.1055 (5)0.3531 (3)0.063 (2)
H11A0.3021−0.08430.32910.076*
H11B0.3073−0.12020.38880.076*
C120.2318 (4)−0.2082 (6)0.3330 (4)0.093 (3)
H12A0.2088−0.23450.35980.112*
H12B0.2656−0.26740.32900.112*
C130.1731 (4)−0.1935 (5)0.2798 (4)0.083 (3)
H13A0.1450−0.26390.27050.100*
H13B0.1959−0.17800.25150.100*
C140.1214 (4)−0.0946 (5)0.2828 (3)0.066 (2)
H14A0.0878−0.08020.24690.079*
H14B0.0924−0.11590.30650.079*
C150.1663 (3)0.2562 (4)0.3241 (2)0.0273 (11)
H150.19510.24240.36190.033*
C160.2182 (3)0.2680 (4)0.2906 (3)0.0393 (14)
H16A0.19010.27370.25250.047*
H16B0.24890.20000.29510.047*
C170.2670 (4)0.3731 (5)0.3069 (3)0.0567 (19)
H17A0.29770.36530.34420.068*
H17B0.29910.37950.28400.068*
C180.2202 (4)0.4797 (5)0.3012 (3)0.0548 (18)
H18A0.25160.54660.31150.066*
H18B0.19030.48890.26370.066*
C190.1720 (4)0.4693 (5)0.3367 (3)0.0524 (17)
H19A0.14220.53790.33350.063*
H19B0.20220.46260.37420.063*
C200.1219 (3)0.3651 (4)0.3214 (3)0.0383 (14)
H20A0.09210.35880.34590.046*
H20B0.08890.37480.28490.046*
C210.0492 (3)0.1226 (5)0.3471 (2)0.0345 (13)
H210.02830.19910.34800.041*
C220.0919 (3)0.0974 (6)0.4055 (2)0.0460 (15)
H22A0.13040.15440.41820.055*
H22B0.11520.02290.40760.055*
C230.0422 (4)0.0986 (6)0.4416 (3)0.0542 (18)
H23A0.07030.07530.47800.065*
H23B0.02470.17610.44360.065*
C24−0.0217 (4)0.0211 (5)0.4212 (3)0.0526 (17)
H24A−0.05380.02830.44410.063*
H24B−0.0044−0.05750.42340.063*
C25−0.0645 (3)0.0472 (6)0.3641 (3)0.0573 (19)
H25A−0.08690.12240.36250.069*
H25B−0.1037−0.00860.35160.069*
C26−0.0163 (3)0.0450 (5)0.3270 (2)0.0463 (15)
H26A0.0005−0.03280.32460.056*
H26B−0.04510.06880.29090.056*
Au20.558501 (11)0.649071 (17)0.747201 (9)0.03400 (7)
Cl20.71112 (14)0.8119 (2)1.02912 (9)0.0950 (8)
S20.64142 (9)0.69232 (12)0.82842 (6)0.0457 (4)
P20.47804 (7)0.61468 (11)0.66583 (6)0.0289 (3)
O20.67747 (19)0.4891 (3)0.80699 (15)0.0380 (9)
N20.7584 (2)0.5672 (4)0.88067 (19)0.0383 (12)
C270.7002 (3)0.5755 (4)0.8428 (2)0.0319 (12)
C280.7795 (3)0.6585 (4)0.9169 (3)0.0391 (15)
C290.7394 (3)0.6862 (5)0.9526 (2)0.0459 (15)
H290.69740.64490.95220.055*
C300.7625 (4)0.7735 (6)0.9876 (3)0.0558 (18)
C310.8228 (5)0.8372 (5)0.9890 (3)0.065 (2)
H310.83640.89931.01250.078*
C320.8629 (4)0.8083 (5)0.9551 (3)0.065 (2)
H320.90540.84940.95650.078*
C330.8417 (3)0.7192 (5)0.9189 (3)0.0498 (17)
H330.86950.70030.89590.060*
C340.7241 (3)0.3915 (4)0.8155 (3)0.0430 (15)
H34A0.77200.41360.81370.065*
H34B0.70330.33530.78800.065*
H34C0.72850.35950.85060.065*
C350.5094 (3)0.4928 (4)0.6342 (2)0.0399 (14)
H350.55640.51880.62980.048*
C360.5299 (5)0.3900 (5)0.6697 (3)0.069 (2)
H36A0.48620.35880.67650.083*
H36B0.56420.41210.70430.083*
C370.5648 (5)0.2992 (6)0.6436 (4)0.083 (3)
H37A0.61340.32520.64380.100*
H37B0.57120.23000.66530.100*
C380.5219 (5)0.2710 (6)0.5873 (4)0.087 (3)
H38A0.55090.22070.57170.105*
H38B0.47770.22990.58760.105*
C390.5015 (5)0.3717 (6)0.5537 (4)0.078 (3)
H39A0.46850.34940.51860.094*
H39B0.54540.40440.54770.094*
C400.4645 (4)0.4612 (6)0.5781 (3)0.0598 (19)
H40A0.45620.52910.55540.072*
H40B0.41690.43280.57900.072*
C410.4746 (3)0.7341 (4)0.6197 (2)0.0295 (12)
H410.43760.71600.58510.035*
C420.5479 (3)0.7523 (5)0.6085 (3)0.0514 (18)
H42A0.58610.76360.64270.062*
H42B0.56020.68400.59160.062*
C430.5467 (4)0.8532 (5)0.5724 (4)0.068 (2)
H43A0.59560.86440.56880.082*
H43B0.51330.83730.53660.082*
C440.5228 (4)0.9609 (5)0.5937 (3)0.067 (2)
H44A0.55930.98270.62730.080*
H44B0.51911.02230.56760.080*
C450.4507 (4)0.9440 (5)0.6034 (3)0.063 (2)
H45A0.41320.93110.56900.076*
H45B0.43761.01300.61940.076*
C460.4518 (3)0.8432 (4)0.6408 (3)0.0468 (16)
H46A0.48570.85960.67640.056*
H46B0.40300.83340.64490.056*
C470.3847 (3)0.5955 (4)0.6704 (2)0.0326 (12)
H470.37350.66640.68670.039*
C480.3817 (3)0.5027 (6)0.7098 (3)0.0563 (18)
H48A0.41880.51710.74420.068*
H48B0.39280.42960.69610.068*
C490.3071 (3)0.4967 (7)0.7186 (3)0.064 (2)
H49A0.30600.43260.74230.077*
H49B0.29870.56630.73650.077*
C500.2468 (3)0.4829 (5)0.6664 (3)0.0575 (19)
H50A0.25140.40890.65060.069*
H50B0.19940.48550.67340.069*
C510.2505 (3)0.5755 (6)0.6276 (3)0.0562 (18)
H51A0.23940.64830.64170.067*
H51B0.21320.56170.59330.067*
C520.3248 (3)0.5836 (6)0.6180 (2)0.0507 (17)
H52A0.33330.51530.59920.061*
H52B0.32550.64930.59510.061*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Au10.03475 (13)0.03001 (11)0.02073 (11)−0.00016 (8)0.00333 (9)−0.00099 (8)
Cl10.0336 (9)0.1165 (16)0.0482 (11)0.0002 (9)0.0097 (8)−0.0057 (10)
S10.0525 (9)0.0324 (7)0.0236 (8)0.0111 (6)−0.0039 (7)−0.0048 (6)
P10.0300 (7)0.0245 (6)0.0224 (7)0.0008 (5)0.0061 (6)0.0017 (5)
O10.041 (2)0.0328 (19)0.030 (2)0.0068 (16)0.0014 (17)−0.0036 (16)
N10.040 (3)0.032 (2)0.026 (3)0.0017 (19)0.007 (2)−0.0068 (19)
C10.032 (3)0.027 (3)0.025 (3)0.003 (2)0.010 (2)0.000 (2)
C20.034 (3)0.036 (3)0.021 (3)0.001 (2)−0.001 (2)−0.006 (2)
C30.041 (3)0.045 (3)0.020 (3)−0.008 (3)0.006 (2)−0.001 (2)
C40.029 (3)0.065 (4)0.025 (3)0.003 (3)−0.001 (3)−0.009 (3)
C50.036 (4)0.046 (4)0.050 (4)0.008 (3)−0.002 (3)0.001 (3)
C60.056 (4)0.037 (3)0.058 (5)0.000 (3)0.003 (4)0.021 (3)
C70.036 (3)0.049 (3)0.041 (4)−0.005 (3)0.008 (3)0.007 (3)
C80.056 (4)0.037 (3)0.053 (4)0.015 (3)0.011 (3)−0.004 (3)
C90.044 (3)0.029 (3)0.040 (4)0.004 (2)0.015 (3)0.002 (2)
C100.061 (4)0.054 (4)0.053 (4)0.027 (3)0.018 (4)0.015 (3)
C110.066 (5)0.049 (4)0.083 (6)0.025 (4)0.033 (4)0.020 (4)
C120.051 (5)0.056 (5)0.172 (10)0.023 (4)0.032 (6)0.030 (6)
C130.083 (6)0.026 (3)0.162 (10)−0.014 (3)0.069 (7)−0.028 (5)
C140.054 (4)0.031 (3)0.111 (7)−0.008 (3)0.023 (4)−0.009 (4)
C150.027 (3)0.025 (2)0.030 (3)0.002 (2)0.009 (2)0.003 (2)
C160.038 (3)0.035 (3)0.051 (4)0.001 (2)0.022 (3)−0.001 (3)
C170.048 (4)0.045 (4)0.088 (6)−0.011 (3)0.035 (4)−0.002 (4)
C180.056 (4)0.033 (3)0.082 (5)−0.006 (3)0.030 (4)0.004 (3)
C190.063 (4)0.031 (3)0.065 (5)−0.003 (3)0.021 (4)−0.010 (3)
C200.040 (3)0.031 (3)0.048 (4)0.002 (2)0.020 (3)−0.003 (3)
C210.035 (3)0.037 (3)0.032 (3)−0.003 (2)0.010 (3)0.005 (2)
C220.047 (4)0.067 (4)0.023 (3)−0.013 (3)0.008 (3)−0.005 (3)
C230.073 (5)0.062 (4)0.039 (4)−0.012 (4)0.032 (4)0.000 (3)
C240.059 (4)0.054 (4)0.060 (5)0.002 (3)0.042 (4)0.007 (3)
C250.040 (4)0.064 (4)0.077 (5)−0.001 (3)0.031 (4)0.016 (4)
C260.034 (3)0.063 (4)0.040 (4)−0.007 (3)0.009 (3)0.007 (3)
Au20.02620 (12)0.03448 (12)0.03323 (14)0.00288 (8)−0.00351 (9)−0.00166 (9)
Cl20.0986 (18)0.131 (2)0.0464 (13)0.0114 (15)0.0074 (12)−0.0290 (13)
S20.0438 (9)0.0354 (7)0.0410 (9)0.0104 (6)−0.0135 (7)−0.0075 (7)
P20.0234 (7)0.0268 (6)0.0313 (8)0.0025 (5)0.0002 (6)−0.0014 (6)
O20.035 (2)0.0267 (18)0.043 (2)0.0008 (15)−0.0019 (18)−0.0025 (17)
N20.031 (3)0.033 (2)0.039 (3)0.0005 (19)−0.006 (2)0.002 (2)
C270.030 (3)0.026 (3)0.036 (3)−0.002 (2)0.004 (2)0.004 (2)
C280.027 (3)0.032 (3)0.044 (4)0.003 (2)−0.012 (3)0.008 (2)
C290.038 (4)0.057 (4)0.032 (4)−0.001 (3)−0.005 (3)0.002 (3)
C300.053 (4)0.061 (4)0.037 (4)0.009 (3)−0.012 (3)−0.004 (3)
C310.072 (6)0.041 (4)0.056 (5)0.007 (3)−0.020 (4)−0.005 (3)
C320.043 (4)0.040 (4)0.085 (6)−0.015 (3)−0.021 (4)0.009 (4)
C330.036 (4)0.043 (3)0.061 (5)−0.001 (3)0.000 (3)0.012 (3)
C340.041 (3)0.027 (3)0.058 (4)0.003 (2)0.010 (3)−0.002 (3)
C350.036 (3)0.029 (3)0.053 (4)0.008 (2)0.012 (3)−0.004 (3)
C360.091 (6)0.042 (4)0.080 (6)0.027 (4)0.033 (5)0.016 (4)
C370.096 (7)0.033 (4)0.140 (9)0.033 (4)0.064 (7)0.021 (5)
C380.112 (7)0.042 (4)0.135 (9)−0.002 (4)0.079 (7)−0.027 (5)
C390.094 (6)0.053 (4)0.092 (7)0.013 (4)0.032 (5)−0.035 (4)
C400.060 (4)0.052 (4)0.065 (5)0.008 (3)0.014 (4)−0.026 (4)
C410.026 (3)0.030 (3)0.029 (3)0.000 (2)0.003 (2)−0.001 (2)
C420.041 (4)0.038 (3)0.084 (5)0.001 (3)0.033 (4)0.000 (3)
C430.082 (6)0.039 (4)0.104 (7)−0.010 (3)0.060 (5)0.000 (4)
C440.069 (5)0.038 (4)0.100 (7)−0.014 (3)0.037 (5)−0.003 (4)
C450.067 (5)0.032 (3)0.099 (6)0.011 (3)0.038 (5)0.010 (4)
C460.040 (4)0.030 (3)0.072 (5)0.004 (2)0.019 (3)0.001 (3)
C470.021 (3)0.036 (3)0.038 (3)−0.001 (2)0.004 (2)0.001 (2)
C480.038 (4)0.067 (4)0.057 (5)−0.002 (3)0.004 (3)0.025 (4)
C490.049 (4)0.089 (5)0.061 (5)−0.005 (4)0.026 (4)0.021 (4)
C500.036 (4)0.051 (4)0.090 (6)−0.004 (3)0.026 (4)0.007 (4)
C510.024 (3)0.075 (5)0.063 (5)−0.005 (3)0.003 (3)0.004 (4)
C520.023 (3)0.086 (5)0.037 (4)−0.002 (3)0.000 (3)0.011 (3)

Geometric parameters (Å, °)

Au1—P12.2565 (14)Au2—P22.2572 (14)
Au1—S12.2982 (14)Au2—S22.2949 (15)
Cl1—C41.733 (6)Cl2—C301.727 (8)
S1—C11.741 (5)S2—C271.748 (5)
P1—C211.834 (6)P2—C411.839 (5)
P1—C91.844 (5)P2—C351.844 (5)
P1—C151.847 (5)P2—C471.845 (5)
O1—C11.357 (6)O2—C271.362 (6)
O1—C81.438 (6)O2—C341.434 (6)
N1—C11.257 (6)N2—C271.255 (6)
N1—C21.430 (7)N2—C281.409 (7)
C2—C31.391 (8)C28—C331.379 (8)
C2—C71.392 (7)C28—C291.411 (9)
C3—C41.367 (8)C29—C301.358 (9)
C3—H30.9400C29—H290.9400
C4—C51.360 (9)C30—C311.372 (10)
C5—C61.366 (9)C31—C321.377 (11)
C5—H50.9400C31—H310.9400
C6—C71.387 (8)C32—C331.390 (9)
C6—H60.9400C32—H320.9400
C7—H70.9400C33—H330.9400
C8—H8A0.9700C34—H34A0.9700
C8—H8B0.9700C34—H34B0.9700
C8—H8C0.9700C34—H34C0.9700
C9—C141.503 (8)C35—C361.503 (8)
C9—C101.524 (8)C35—C401.507 (8)
C9—H90.9900C35—H350.9900
C10—C111.509 (8)C36—C371.526 (10)
C10—H10A0.9800C36—H36A0.9800
C10—H10B0.9800C36—H36B0.9800
C11—C121.459 (10)C37—C381.490 (12)
C11—H11A0.9800C37—H37A0.9800
C11—H11B0.9800C37—H37B0.9800
C12—C131.513 (12)C38—C391.458 (11)
C12—H12A0.9800C38—H38A0.9800
C12—H12B0.9800C38—H38B0.9800
C13—C141.549 (9)C39—C401.513 (8)
C13—H13A0.9800C39—H39A0.9800
C13—H13B0.9800C39—H39B0.9800
C14—H14A0.9800C40—H40A0.9800
C14—H14B0.9800C40—H40B0.9800
C15—C161.514 (7)C41—C461.515 (7)
C15—C201.530 (7)C41—C421.535 (7)
C15—H150.9900C41—H410.9900
C16—C171.535 (8)C42—C431.512 (9)
C16—H16A0.9800C42—H42A0.9800
C16—H16B0.9800C42—H42B0.9800
C17—C181.526 (8)C43—C441.509 (9)
C17—H17A0.9800C43—H43A0.9800
C17—H17B0.9800C43—H43B0.9800
C18—C191.495 (9)C44—C451.494 (9)
C18—H18A0.9800C44—H44A0.9800
C18—H18B0.9800C44—H44B0.9800
C19—C201.538 (7)C45—C461.533 (8)
C19—H19A0.9800C45—H45A0.9800
C19—H19B0.9800C45—H45B0.9800
C20—H20A0.9800C46—H46A0.9800
C20—H20B0.9800C46—H46B0.9800
C21—C261.517 (7)C47—C521.506 (7)
C21—C221.526 (8)C47—C481.513 (8)
C21—H210.9900C47—H470.9900
C22—C231.527 (8)C48—C491.517 (9)
C22—H22A0.9800C48—H48A0.9800
C22—H22B0.9800C48—H48B0.9800
C23—C241.496 (9)C49—C501.509 (9)
C23—H23A0.9800C49—H49A0.9800
C23—H23B0.9800C49—H49B0.9800
C24—C251.502 (9)C50—C511.504 (9)
C24—H24A0.9800C50—H50A0.9800
C24—H24B0.9800C50—H50B0.9800
C25—C261.523 (8)C51—C521.524 (8)
C25—H25A0.9800C51—H51A0.9800
C25—H25B0.9800C51—H51B0.9800
C26—H26A0.9800C52—H52A0.9800
C26—H26B0.9800C52—H52B0.9800
P1—Au1—S1175.10 (5)P2—Au2—S2177.26 (5)
C1—S1—Au1104.79 (18)C27—S2—Au2104.42 (19)
C21—P1—C9112.0 (3)C41—P2—C35104.9 (3)
C21—P1—C15106.5 (2)C41—P2—C47106.8 (2)
C9—P1—C15105.0 (2)C35—P2—C47112.7 (3)
C21—P1—Au1112.04 (19)C41—P2—Au2110.99 (17)
C9—P1—Au1111.61 (19)C35—P2—Au2109.64 (19)
C15—P1—Au1109.31 (17)C47—P2—Au2111.58 (19)
C1—O1—C8116.1 (4)C27—O2—C34115.8 (4)
C1—N1—C2117.1 (4)C27—N2—C28118.5 (5)
N1—C1—O1121.1 (5)N2—C27—O2120.6 (5)
N1—C1—S1125.3 (4)N2—C27—S2126.7 (4)
O1—C1—S1113.6 (4)O2—C27—S2112.8 (4)
C3—C2—C7119.2 (5)C33—C28—N2119.6 (6)
C3—C2—N1119.6 (5)C33—C28—C29119.4 (6)
C7—C2—N1121.1 (5)N2—C28—C29121.0 (5)
C4—C3—C2119.4 (5)C30—C29—C28119.1 (6)
C4—C3—H3120.3C30—C29—H29120.5
C2—C3—H3120.3C28—C29—H29120.5
C5—C4—C3122.1 (6)C29—C30—C31122.4 (7)
C5—C4—Cl1119.7 (5)C29—C30—Cl2119.1 (6)
C3—C4—Cl1118.1 (5)C31—C30—Cl2118.3 (6)
C4—C5—C6118.9 (6)C30—C31—C32118.5 (7)
C4—C5—H5120.6C30—C31—H31120.8
C6—C5—H5120.6C32—C31—H31120.8
C5—C6—C7121.2 (6)C31—C32—C33121.0 (7)
C5—C6—H6119.4C31—C32—H32119.5
C7—C6—H6119.4C33—C32—H32119.5
C6—C7—C2119.2 (6)C28—C33—C32119.6 (7)
C6—C7—H7120.4C28—C33—H33120.2
C2—C7—H7120.4C32—C33—H33120.2
O1—C8—H8A109.5O2—C34—H34A109.5
O1—C8—H8B109.5O2—C34—H34B109.5
H8A—C8—H8B109.5H34A—C34—H34B109.5
O1—C8—H8C109.5O2—C34—H34C109.5
H8A—C8—H8C109.5H34A—C34—H34C109.5
H8B—C8—H8C109.5H34B—C34—H34C109.5
C14—C9—C10111.8 (5)C36—C35—C40111.5 (5)
C14—C9—P1112.4 (4)C36—C35—P2114.5 (5)
C10—C9—P1117.3 (4)C40—C35—P2117.2 (4)
C14—C9—H9104.6C36—C35—H35103.9
C10—C9—H9104.6C40—C35—H35103.9
P1—C9—H9104.6P2—C35—H35103.9
C11—C10—C9112.9 (6)C35—C36—C37111.1 (6)
C11—C10—H10A109.0C35—C36—H36A109.4
C9—C10—H10A109.0C37—C36—H36A109.4
C11—C10—H10B109.0C35—C36—H36B109.4
C9—C10—H10B109.0C37—C36—H36B109.4
H10A—C10—H10B107.8H36A—C36—H36B108.0
C12—C11—C10110.8 (6)C38—C37—C36114.1 (7)
C12—C11—H11A109.5C38—C37—H37A108.7
C10—C11—H11A109.5C36—C37—H37A108.7
C12—C11—H11B109.5C38—C37—H37B108.7
C10—C11—H11B109.5C36—C37—H37B108.7
H11A—C11—H11B108.1H37A—C37—H37B107.6
C11—C12—C13114.4 (6)C39—C38—C37112.4 (6)
C11—C12—H12A108.7C39—C38—H38A109.1
C13—C12—H12A108.7C37—C38—H38A109.1
C11—C12—H12B108.7C39—C38—H38B109.1
C13—C12—H12B108.7C37—C38—H38B109.1
H12A—C12—H12B107.6H38A—C38—H38B107.9
C12—C13—C14110.7 (7)C38—C39—C40113.1 (7)
C12—C13—H13A109.5C38—C39—H39A109.0
C14—C13—H13A109.5C40—C39—H39A109.0
C12—C13—H13B109.5C38—C39—H39B109.0
C14—C13—H13B109.5C40—C39—H39B109.0
H13A—C13—H13B108.1H39A—C39—H39B107.8
C9—C14—C13111.2 (6)C35—C40—C39112.1 (6)
C9—C14—H14A109.4C35—C40—H40A109.2
C13—C14—H14A109.4C39—C40—H40A109.2
C9—C14—H14B109.4C35—C40—H40B109.2
C13—C14—H14B109.4C39—C40—H40B109.2
H14A—C14—H14B108.0H40A—C40—H40B107.9
C16—C15—C20110.5 (4)C46—C41—C42109.3 (4)
C16—C15—P1110.6 (4)C46—C41—P2111.7 (4)
C20—C15—P1109.4 (4)C42—C41—P2112.0 (4)
C16—C15—H15108.8C46—C41—H41107.9
C20—C15—H15108.8C42—C41—H41107.9
P1—C15—H15108.8P2—C41—H41107.9
C15—C16—C17111.5 (5)C43—C42—C41112.5 (5)
C15—C16—H16A109.3C43—C42—H42A109.1
C17—C16—H16A109.3C41—C42—H42A109.1
C15—C16—H16B109.3C43—C42—H42B109.1
C17—C16—H16B109.3C41—C42—H42B109.1
H16A—C16—H16B108.0H42A—C42—H42B107.8
C18—C17—C16110.2 (5)C44—C43—C42112.6 (6)
C18—C17—H17A109.6C44—C43—H43A109.1
C16—C17—H17A109.6C42—C43—H43A109.1
C18—C17—H17B109.6C44—C43—H43B109.1
C16—C17—H17B109.6C42—C43—H43B109.1
H17A—C17—H17B108.1H43A—C43—H43B107.8
C19—C18—C17109.1 (5)C45—C44—C43110.4 (5)
C19—C18—H18A109.9C45—C44—H44A109.6
C17—C18—H18A109.9C43—C44—H44A109.6
C19—C18—H18B109.9C45—C44—H44B109.6
C17—C18—H18B109.9C43—C44—H44B109.6
H18A—C18—H18B108.3H44A—C44—H44B108.1
C18—C19—C20111.1 (5)C44—C45—C46111.9 (6)
C18—C19—H19A109.4C44—C45—H45A109.2
C20—C19—H19A109.4C46—C45—H45A109.2
C18—C19—H19B109.4C44—C45—H45B109.2
C20—C19—H19B109.4C46—C45—H45B109.2
H19A—C19—H19B108.0H45A—C45—H45B107.9
C15—C20—C19111.1 (5)C41—C46—C45112.2 (6)
C15—C20—H20A109.4C41—C46—H46A109.2
C19—C20—H20A109.4C45—C46—H46A109.2
C15—C20—H20B109.4C41—C46—H46B109.2
C19—C20—H20B109.4C45—C46—H46B109.2
H20A—C20—H20B108.0H46A—C46—H46B107.9
C26—C21—C22111.8 (5)C52—C47—C48112.1 (5)
C26—C21—P1113.5 (4)C52—C47—P2116.5 (4)
C22—C21—P1115.8 (4)C48—C47—P2111.5 (4)
C26—C21—H21104.8C52—C47—H47105.2
C22—C21—H21104.8C48—C47—H47105.2
P1—C21—H21104.8P2—C47—H47105.2
C21—C22—C23111.3 (5)C47—C48—C49111.4 (5)
C21—C22—H22A109.4C47—C48—H48A109.4
C23—C22—H22A109.4C49—C48—H48A109.4
C21—C22—H22B109.4C47—C48—H48B109.4
C23—C22—H22B109.4C49—C48—H48B109.4
H22A—C22—H22B108.0H48A—C48—H48B108.0
C24—C23—C22111.9 (5)C50—C49—C48112.0 (6)
C24—C23—H23A109.2C50—C49—H49A109.2
C22—C23—H23A109.2C48—C49—H49A109.2
C24—C23—H23B109.2C50—C49—H49B109.2
C22—C23—H23B109.2C48—C49—H49B109.2
H23A—C23—H23B107.9H49A—C49—H49B107.9
C23—C24—C25112.1 (5)C51—C50—C49110.4 (5)
C23—C24—H24A109.2C51—C50—H50A109.6
C25—C24—H24A109.2C49—C50—H50A109.6
C23—C24—H24B109.2C51—C50—H50B109.6
C25—C24—H24B109.2C49—C50—H50B109.6
H24A—C24—H24B107.9H50A—C50—H50B108.1
C24—C25—C26111.7 (5)C50—C51—C52113.0 (5)
C24—C25—H25A109.3C50—C51—H51A109.0
C26—C25—H25A109.3C52—C51—H51A109.0
C24—C25—H25B109.3C50—C51—H51B109.0
C26—C25—H25B109.3C52—C51—H51B109.0
H25A—C25—H25B107.9H51A—C51—H51B107.8
C21—C26—C25111.6 (5)C47—C52—C51110.8 (5)
C21—C26—H26A109.3C47—C52—H52A109.5
C25—C26—H26A109.3C51—C52—H52A109.5
C21—C26—H26B109.3C47—C52—H52B109.5
C25—C26—H26B109.3C51—C52—H52B109.5
H26A—C26—H26B108.0H52A—C52—H52B108.1
C2—N1—C1—O1177.6 (5)C28—N2—C27—O2−179.7 (5)
C2—N1—C1—S1−2.0 (7)C28—N2—C27—S21.6 (8)
C8—O1—C1—N1−0.8 (7)C34—O2—C27—N2−0.4 (8)
C8—O1—C1—S1178.9 (4)C34—O2—C27—S2178.5 (4)
Au1—S1—C1—N1167.3 (4)Au2—S2—C27—N2172.1 (5)
Au1—S1—C1—O1−12.3 (4)Au2—S2—C27—O2−6.7 (4)
C1—N1—C2—C3−89.4 (6)C27—N2—C28—C33−114.0 (6)
C1—N1—C2—C793.4 (6)C27—N2—C28—C2968.4 (7)
C7—C2—C3—C4−3.0 (8)C33—C28—C29—C301.1 (8)
N1—C2—C3—C4179.8 (5)N2—C28—C29—C30178.7 (5)
C2—C3—C4—C51.9 (9)C28—C29—C30—C311.1 (10)
C2—C3—C4—Cl1−179.1 (4)C28—C29—C30—Cl2176.9 (4)
C3—C4—C5—C60.2 (10)C29—C30—C31—C32−2.8 (10)
Cl1—C4—C5—C6−178.8 (5)Cl2—C30—C31—C32−178.6 (5)
C4—C5—C6—C7−1.2 (10)C30—C31—C32—C332.3 (10)
C5—C6—C7—C20.1 (10)N2—C28—C33—C32−179.2 (5)
C3—C2—C7—C62.0 (9)C29—C28—C33—C32−1.6 (9)
N1—C2—C7—C6179.2 (5)C31—C32—C33—C28−0.1 (10)
C21—P1—C9—C1467.9 (5)C41—P2—C35—C36169.1 (5)
C15—P1—C9—C14−177.0 (5)C47—P2—C35—C36−75.0 (5)
Au1—P1—C9—C14−58.7 (5)Au2—P2—C35—C3649.9 (5)
C21—P1—C9—C10−63.9 (5)C41—P2—C35—C40−57.4 (5)
C15—P1—C9—C1051.2 (5)C47—P2—C35—C4058.4 (6)
Au1—P1—C9—C10169.6 (4)Au2—P2—C35—C40−176.7 (4)
C14—C9—C10—C1153.5 (8)C40—C35—C36—C3751.6 (8)
P1—C9—C10—C11−174.5 (5)P2—C35—C36—C37−172.3 (6)
C9—C10—C11—C12−53.4 (9)C35—C36—C37—C38−50.7 (10)
C10—C11—C12—C1354.6 (10)C36—C37—C38—C3950.8 (10)
C11—C12—C13—C14−54.2 (9)C37—C38—C39—C40−51.7 (10)
C10—C9—C14—C13−52.3 (8)C36—C35—C40—C39−53.6 (8)
P1—C9—C14—C13173.3 (6)P2—C35—C40—C39171.7 (5)
C12—C13—C14—C952.0 (9)C38—C39—C40—C3553.8 (10)
C21—P1—C15—C16175.3 (4)C35—P2—C41—C46−178.2 (4)
C9—P1—C15—C1656.4 (4)C47—P2—C41—C4662.0 (4)
Au1—P1—C15—C16−63.5 (4)Au2—P2—C41—C46−59.9 (4)
C21—P1—C15—C20−62.7 (4)C35—P2—C41—C42−55.2 (5)
C9—P1—C15—C20178.4 (4)C47—P2—C41—C42−175.0 (4)
Au1—P1—C15—C2058.5 (4)Au2—P2—C41—C4263.1 (4)
C20—C15—C16—C1754.5 (6)C46—C41—C42—C43−53.3 (7)
P1—C15—C16—C17175.8 (4)P2—C41—C42—C43−177.6 (5)
C15—C16—C17—C18−57.9 (7)C41—C42—C43—C4454.6 (9)
C16—C17—C18—C1959.7 (8)C42—C43—C44—C45−54.7 (9)
C17—C18—C19—C20−59.7 (7)C43—C44—C45—C4655.2 (9)
C16—C15—C20—C19−53.6 (7)C42—C41—C46—C4554.0 (7)
P1—C15—C20—C19−175.6 (4)P2—C41—C46—C45178.5 (5)
C18—C19—C20—C1557.2 (7)C44—C45—C46—C41−56.6 (8)
C9—P1—C21—C26−78.6 (5)C41—P2—C47—C5252.6 (5)
C15—P1—C21—C26167.1 (4)C35—P2—C47—C52−62.1 (5)
Au1—P1—C21—C2647.7 (4)Au2—P2—C47—C52174.1 (4)
C9—P1—C21—C2252.7 (5)C41—P2—C47—C48−177.1 (4)
C15—P1—C21—C22−61.6 (5)C35—P2—C47—C4868.3 (5)
Au1—P1—C21—C22179.0 (4)Au2—P2—C47—C48−55.6 (5)
C26—C21—C22—C23−52.8 (7)C52—C47—C48—C49−54.3 (8)
P1—C21—C22—C23175.1 (4)P2—C47—C48—C49173.0 (5)
C21—C22—C23—C2453.7 (7)C47—C48—C49—C5055.0 (8)
C22—C23—C24—C25−55.1 (8)C48—C49—C50—C51−54.7 (8)
C23—C24—C25—C2655.2 (8)C49—C50—C51—C5254.6 (8)
C22—C21—C26—C2553.2 (7)C48—C47—C52—C5153.3 (7)
P1—C21—C26—C25−173.6 (4)P2—C47—C52—C51−176.6 (4)
C24—C25—C26—C21−54.1 (7)C50—C51—C52—C47−54.1 (8)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: PV2267).

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