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Acta Crystallogr Sect E Struct Rep Online. 2010 June 1; 66(Pt 6): m622–m623.
Published online 2010 May 8. doi:  10.1107/S1600536810016326
PMCID: PMC2979488

[μ-1,2-Bis(diphenyl­phosphino)methane-κ2 P:P′]bis­{[(Z)-O-ethyl N-(4-nitro­phen­yl)thio­carbamato-κS]gold(I)}

Abstract

Each gold atom in the binuclear title compound, [Au2(C9H9N2O3S)2(C25H22P2)], is coordinated within an S,P-donor set that defines a slightly distorted linear geometry [S—Au—P angles = 172.77 (6) and 173.84 (6)°], with the distortion due in part to a close intra­molecular Au(...)O contact [2.968 (11) and 2.963 (4) Å]. The mol­ecule adopts a U-shaped conformation allowing for the formation of an aurophilic Au(...)Au inter­action [3.2320 (5) Å]. Mol­ecules are consolidated in the crystal structure by C—H(...)π inter­actions. Disorder was noted for one of the eth­oxy groups with two orientations being resolved in a 0.679 (16):0.321 (16) ratio.

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-66-0m622-scheme1.jpg

Experimental

Crystal data

  • [Au2(C9H9N2O3S)2(C25H22P2)]
  • M r = 1228.83
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-0m622-efi1.jpg
  • a = 24.400 (3) Å
  • b = 16.1419 (16) Å
  • c = 24.594 (2) Å
  • β = 110.252 (9)°
  • V = 9087.9 (16) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 6.66 mm−1
  • T = 223 K
  • 0.31 × 0.13 × 0.05 mm

Data collection

  • Bruker SMART CCD diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2000 [triangle]) T min = 0.445, T max = 1
  • 31967 measured reflections
  • 10427 independent reflections
  • 7923 reflections with I > 2σ(I)
  • R int = 0.053

Refinement

  • R[F 2 > 2σ(F 2)] = 0.039
  • wR(F 2) = 0.110
  • S = 1.02
  • 10427 reflections
  • 549 parameters
  • 28 restraints
  • H-atom parameters constrained
  • Δρmax = 1.52 e Å−3
  • Δρmin = −1.19 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]) and DIAMOND (Brandenburg, 2006 [triangle]); software used to prepare material for publication: publCIF (Westrip, 2010 [triangle]).

Table 1
Selected bond lengths (Å)
Table 2
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810016326/hb5435sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810016326/hb5435Isup2.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

The investigation of dinuclear molecules related to molecules with the general formula R3PAu[SC(OR')═ NR''], for R, R' and R'' = alkyl and aryl,have proved useful for crystal engineering studies, in particular in terms of a competition between intra- and inter-molecular aurophilic (Au···Au) interactions, and the influence of these upon luminescence (Ho et al., 2006; Ho & Tiekink, 2007; Kuan et al., 2008). The title compound, (I), is the ethoxy analogue of the previously reported methoxy derivative (Ho et al., 2006).

The nearly linear SP coordination geometry observed for each Au atom, Fig. 1, is defined by one P atom of the bidentate bridging diphosphine ligand and the thiolate-S derived from the carbonimidothioate anion, Table 1. Deviations from the ideal linearity [S—Au—P = 172.77 (6) and 173.84 (6) °] is traced to the close intramolecular Au···O contacts [2.968 (11) and 2.963 (4) Å]. Overall, the conformation of the dinuclear molecule is a U-shape which allows for the formation of an intramolecular Au···Au contact of 3.2320 (5) Å which is longer than 3.1589 (4) Å found in the methoxy derivative (Ho et al. 2006).

The major feature of the crystal packing is the presence of C–H···π interactions, Table 2 and Fig. 2.

Experimental

Compound (I) was prepared following the standard literature procedure from the reaction of [Ph2PCH2PPh2](AuCl)2 and EtOC(═S)N(H)(C6H4NO2-4) in the presence of NaOH (Hall et al., 1993). Yellow blocks of (I) were obtained by the slow evaporation of a CHCl3/hexane (3/1) solution held at room temperature; m.pt. 483 K. Analysis, Found (Calculated): C 41.97 (42.03); H 3.67 (3.28); N 4.09 (4.56); S 4.64 (5.20). IR (KBr, cm-1): ν(C–S) 1103 (s), 851 (m); ν(C–N) 1580 (m); ν(C–O) 1144 (s). 31P{1H} (CDCl3) NMR: δ 29.2 p.p.m.

Refinement

The H atoms were geometrically placed (C—H = 0.94–0.98 Å) and refined as riding with Uiso(H) = 1.2-1.5Ueq(C). The maximum and minimum residual electron density peaks of 1.52 and 1.19 e Å-3, respectively, were located 0.90 Å and 1.53 Å from the Au1 and Au2 atoms, respectively. High thermal motion was noted in the O1-ethoxy substituent but only two positions were resolved for each of three atoms. Anisotropic refinement (constrained to be equivalent for paired components of the disorder, and approximately isotropic by the EADP and ISOR commands in SHELXL-97 (Sheldrick, 2008), respectively) and with the O–C and C–C distances restrained to 1.45+0.01 and 1.48±0.01 Å showed the major component of the disorder had a site occupancy factor = 0.679 (16).

Figures

Fig. 1.
Molecular structure of (I) showing displacement ellipsoids at the 50% probability level. Only the major component of the disordered ethoxy group is shown for reasons of clarity.
Fig. 2.
A view in projection down the b axis of the crystal packing in (I). The C–H···π contacts are shown as purple dashed lines.

Crystal data

[Au2(C9H9N2O3S)2(C25H22P2)]F(000) = 4751
Mr = 1228.83Dx = 1.796 Mg m3
Monoclinic, I2/aMo Kα radiation, λ = 0.71069 Å
Hall symbol: -I 2yaCell parameters from 5597 reflections
a = 24.400 (3) Åθ = 2.5–24.2°
b = 16.1419 (16) ŵ = 6.66 mm1
c = 24.594 (2) ÅT = 223 K
β = 110.252 (9)°Block, yellow
V = 9087.9 (16) Å30.31 × 0.13 × 0.05 mm
Z = 8

Data collection

Bruker SMART CCD diffractometer10427 independent reflections
Radiation source: fine-focus sealed tube7923 reflections with I > 2σ(I)
graphiteRint = 0.053
ω scansθmax = 27.5°, θmin = 1.5°
Absorption correction: multi-scan (SADABS; Bruker, 2000)h = −27→31
Tmin = 0.445, Tmax = 1k = −20→20
31967 measured reflectionsl = −31→24

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)] = 0.039Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.110H-atom parameters constrained
S = 1.02w = 1/[σ2(Fo2) + (0.0567P)2] where P = (Fo2 + 2Fc2)/3
10427 reflections(Δ/σ)max = 0.001
549 parametersΔρmax = 1.52 e Å3
28 restraintsΔρmin = −1.19 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*/UeqOcc. (<1)
Au11.009521 (10)0.859132 (13)0.324297 (11)0.03469 (8)
Au20.879170 (10)0.815714 (13)0.237856 (11)0.03270 (8)
S10.99717 (8)0.99888 (10)0.33639 (8)0.0448 (4)
S20.84758 (7)0.93438 (9)0.18429 (8)0.0408 (4)
P11.03352 (6)0.72491 (9)0.31943 (7)0.0290 (3)
P20.90430 (7)0.69252 (9)0.28151 (7)0.0288 (3)
O20.9091 (3)1.4064 (3)0.3450 (3)0.0745 (18)
O30.9791 (3)1.4426 (3)0.3166 (3)0.0731 (17)
O40.7826 (2)0.8134 (3)0.1245 (2)0.0553 (14)
O50.7025 (4)1.3205 (4)0.1153 (3)0.096 (3)
O60.7716 (4)1.3265 (4)0.0808 (4)0.111 (3)
N11.0713 (3)1.0927 (3)0.4211 (3)0.0595 (18)
N20.9560 (3)1.3930 (3)0.3388 (3)0.0514 (16)
N30.7433 (2)0.9417 (4)0.0988 (3)0.0548 (17)
N40.7390 (4)1.2877 (4)0.0992 (3)0.071 (2)
C11.0559 (3)1.0213 (4)0.4003 (3)0.0517 (19)
C21.0404 (3)1.1643 (4)0.3968 (3)0.0430 (17)
C30.9831 (3)1.1771 (4)0.3941 (3)0.0470 (17)
H30.96331.13430.40550.056*
C40.9546 (3)1.2513 (4)0.3751 (3)0.0421 (16)
H40.91601.25960.37350.051*
C50.9849 (3)1.3130 (3)0.3584 (3)0.0366 (14)
C61.0423 (3)1.3030 (4)0.3607 (3)0.0422 (16)
H61.06221.34600.34960.051*
C71.0689 (3)1.2284 (4)0.3796 (3)0.0458 (16)
H71.10751.22020.38100.055*
O11.0910 (5)0.9539 (9)0.4226 (5)0.053 (3)0.679 (16)
C81.1390 (6)0.9687 (10)0.4772 (5)0.071 (4)0.679 (16)
H8A1.15831.02110.47490.085*0.679 (16)
H8B1.16790.92410.48400.085*0.679 (16)
C91.1167 (9)0.9720 (13)0.5257 (9)0.129 (7)0.679 (16)
H9A1.08051.00330.51400.194*0.679 (16)
H9B1.14530.99860.55870.194*0.679 (16)
H9C1.10940.91610.53610.194*0.679 (16)
O1A1.0752 (12)0.955 (2)0.4357 (11)0.053 (3)0.321 (16)
C8A1.1194 (13)0.962 (3)0.4932 (13)0.071 (4)0.321 (16)
H8C1.11970.91180.51540.085*0.321 (16)
H8D1.11041.00920.51390.085*0.321 (16)
C9A1.1774 (18)0.974 (3)0.488 (2)0.129 (7)0.321 (16)
H9D1.18970.92350.47460.194*0.321 (16)
H9E1.20550.98950.52540.194*0.321 (16)
H9F1.17511.01840.46030.194*0.321 (16)
C100.7841 (3)0.8975 (4)0.1301 (3)0.0420 (16)
C110.7461 (3)1.0285 (4)0.1030 (3)0.0500 (19)
C120.7136 (3)1.0705 (4)0.1311 (3)0.0457 (17)
H120.69281.04060.15040.055*
C130.7120 (3)1.1557 (5)0.1307 (3)0.0523 (18)
H130.69051.18440.14990.063*
C140.7421 (3)1.1983 (4)0.1020 (3)0.0501 (19)
C150.7755 (4)1.1598 (5)0.0743 (4)0.064 (2)
H150.79701.19100.05640.076*
C160.7768 (3)1.0742 (5)0.0736 (4)0.060 (2)
H160.79811.04650.05370.072*
C170.7306 (4)0.7781 (5)0.0805 (4)0.073 (3)
H17A0.72520.80220.04250.087*
H17B0.69570.79000.09030.087*
C180.7394 (5)0.6876 (5)0.0793 (5)0.105 (4)
H18A0.77370.67640.06890.157*
H18B0.70540.66240.05080.157*
H18C0.74500.66440.11720.157*
C190.9736 (2)0.6572 (3)0.2764 (3)0.0286 (12)
H19A0.97120.65780.23580.034*
H19B0.98140.60010.29070.034*
C201.0897 (2)0.7147 (4)0.2871 (3)0.0292 (12)
C211.1218 (3)0.7832 (4)0.2835 (3)0.0387 (14)
H211.11390.83470.29700.046*
C221.1651 (3)0.7771 (4)0.2603 (3)0.0447 (16)
H221.18700.82430.25840.054*
C231.1770 (3)0.7024 (4)0.2398 (3)0.0461 (17)
H231.20650.69910.22340.055*
C241.1458 (3)0.6324 (4)0.2431 (3)0.0434 (16)
H241.15420.58120.22960.052*
C251.1021 (3)0.6386 (4)0.2667 (3)0.0377 (14)
H251.08050.59130.26890.045*
C261.0615 (3)0.6760 (4)0.3902 (3)0.0346 (14)
C271.0727 (3)0.7253 (5)0.4402 (3)0.0447 (16)
H271.06680.78290.43690.054*
C281.0923 (3)0.6884 (6)0.4935 (3)0.061 (2)
H281.10020.72130.52690.073*
C291.1006 (3)0.6060 (6)0.4992 (3)0.061 (2)
H291.11360.58200.53630.074*
C301.0899 (3)0.5563 (5)0.4507 (3)0.0519 (19)
H301.09570.49870.45510.062*
C311.0707 (3)0.5910 (4)0.3953 (3)0.0413 (15)
H311.06420.55780.36230.050*
C320.8515 (2)0.6121 (4)0.2458 (3)0.0328 (13)
C330.8615 (3)0.5573 (4)0.2072 (3)0.0415 (16)
H330.89730.55780.20060.050*
C340.8178 (3)0.5010 (4)0.1779 (3)0.0481 (17)
H340.82420.46340.15150.058*
C350.7657 (3)0.4999 (4)0.1874 (3)0.055 (2)
H350.73640.46230.16700.066*
C360.7564 (4)0.5527 (5)0.2257 (4)0.062 (2)
H360.72080.55130.23240.075*
C370.7994 (3)0.6095 (5)0.2554 (4)0.0527 (19)
H370.79270.64610.28220.063*
C380.9131 (2)0.6901 (3)0.3575 (3)0.0315 (13)
C390.9128 (3)0.7625 (4)0.3875 (3)0.0413 (15)
H390.90560.81330.36750.050*
C400.9232 (3)0.7613 (5)0.4467 (3)0.0521 (19)
H400.92240.81090.46650.063*
C410.9344 (3)0.6881 (5)0.4761 (3)0.054 (2)
H410.94240.68760.51630.065*
C420.9342 (3)0.6141 (5)0.4468 (3)0.056 (2)
H420.94130.56370.46720.067*
C430.9234 (3)0.6149 (4)0.3873 (3)0.0415 (15)
H430.92320.56510.36730.050*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Au10.03798 (14)0.02598 (12)0.03917 (15)0.00068 (9)0.01218 (11)−0.00119 (10)
Au20.03173 (13)0.02833 (12)0.03663 (14)0.00304 (9)0.01005 (10)0.00221 (10)
S10.0507 (10)0.0294 (8)0.0440 (10)0.0059 (7)0.0033 (8)−0.0017 (7)
S20.0376 (8)0.0290 (7)0.0470 (10)0.0019 (6)0.0034 (7)0.0043 (7)
P10.0299 (7)0.0259 (7)0.0310 (8)−0.0013 (6)0.0102 (6)0.0011 (6)
P20.0301 (8)0.0263 (7)0.0300 (8)−0.0007 (6)0.0105 (6)−0.0013 (6)
O20.058 (4)0.046 (3)0.119 (6)0.014 (3)0.030 (4)−0.007 (3)
O30.085 (4)0.040 (3)0.088 (5)0.002 (3)0.023 (4)0.014 (3)
O40.047 (3)0.039 (3)0.065 (4)0.001 (2)0.000 (3)−0.002 (2)
O50.152 (7)0.048 (4)0.078 (5)0.023 (4)0.028 (5)0.001 (3)
O60.141 (7)0.057 (4)0.117 (7)−0.035 (4)0.023 (6)0.013 (4)
N10.064 (4)0.028 (3)0.064 (4)0.005 (3)−0.007 (3)−0.005 (3)
N20.057 (4)0.030 (3)0.057 (4)0.001 (3)0.007 (3)−0.001 (3)
N30.039 (3)0.046 (3)0.062 (4)0.005 (3)−0.005 (3)0.001 (3)
N40.098 (6)0.043 (4)0.049 (4)−0.004 (4)−0.006 (4)−0.001 (3)
C10.053 (4)0.032 (3)0.057 (5)0.012 (3)0.002 (4)0.003 (3)
C20.057 (4)0.029 (3)0.033 (4)0.007 (3)0.003 (3)−0.005 (3)
C30.057 (4)0.034 (3)0.053 (5)−0.008 (3)0.024 (4)−0.004 (3)
C40.041 (4)0.036 (3)0.045 (4)−0.008 (3)0.010 (3)−0.014 (3)
C50.045 (4)0.028 (3)0.035 (4)0.003 (3)0.011 (3)−0.005 (3)
C60.063 (4)0.034 (3)0.038 (4)−0.006 (3)0.028 (3)−0.005 (3)
C70.040 (4)0.048 (4)0.051 (4)0.002 (3)0.018 (3)−0.007 (3)
O10.052 (7)0.036 (3)0.055 (6)0.020 (5)−0.003 (4)−0.005 (5)
C80.070 (7)0.061 (5)0.071 (6)0.016 (5)0.008 (5)0.005 (5)
C90.137 (9)0.116 (8)0.122 (9)0.011 (6)0.028 (6)0.001 (6)
O1A0.052 (7)0.036 (3)0.055 (6)0.020 (5)−0.003 (4)−0.005 (5)
C8A0.070 (7)0.061 (5)0.071 (6)0.016 (5)0.008 (5)0.005 (5)
C9A0.137 (9)0.116 (8)0.122 (9)0.011 (6)0.028 (6)0.001 (6)
C100.038 (3)0.034 (3)0.049 (4)0.000 (3)0.009 (3)0.005 (3)
C110.030 (3)0.045 (4)0.061 (5)0.009 (3)−0.003 (3)0.013 (4)
C120.044 (4)0.048 (4)0.039 (4)−0.001 (3)0.008 (3)0.004 (3)
C130.054 (5)0.058 (4)0.041 (4)0.006 (4)0.012 (4)−0.006 (4)
C140.047 (4)0.042 (4)0.045 (4)0.002 (3)−0.004 (3)0.006 (3)
C150.047 (4)0.064 (5)0.075 (6)−0.011 (4)0.014 (4)0.014 (5)
C160.039 (4)0.066 (5)0.076 (6)0.011 (4)0.021 (4)−0.002 (4)
C170.056 (5)0.061 (5)0.077 (6)−0.006 (4)−0.008 (5)−0.010 (5)
C180.108 (9)0.053 (5)0.126 (11)−0.011 (5)0.005 (8)−0.025 (6)
C190.031 (3)0.026 (3)0.029 (3)−0.001 (2)0.011 (2)−0.001 (2)
C200.022 (3)0.035 (3)0.029 (3)−0.002 (2)0.007 (2)0.005 (3)
C210.035 (3)0.036 (3)0.039 (4)−0.002 (3)0.005 (3)0.001 (3)
C220.036 (3)0.048 (4)0.048 (4)−0.010 (3)0.013 (3)0.010 (3)
C230.035 (4)0.057 (4)0.049 (4)0.001 (3)0.019 (3)0.008 (3)
C240.044 (4)0.043 (4)0.048 (4)0.007 (3)0.023 (3)0.006 (3)
C250.041 (3)0.031 (3)0.043 (4)0.002 (3)0.016 (3)0.000 (3)
C260.025 (3)0.044 (3)0.032 (3)−0.001 (2)0.005 (3)0.004 (3)
C270.042 (4)0.052 (4)0.037 (4)0.000 (3)0.009 (3)−0.001 (3)
C280.056 (5)0.092 (7)0.026 (4)0.001 (4)0.003 (3)−0.001 (4)
C290.044 (4)0.097 (7)0.032 (4)0.002 (4)−0.001 (3)0.027 (4)
C300.044 (4)0.054 (4)0.054 (5)0.007 (3)0.012 (4)0.026 (4)
C310.039 (4)0.041 (3)0.043 (4)0.004 (3)0.015 (3)0.008 (3)
C320.029 (3)0.032 (3)0.037 (3)0.001 (2)0.010 (3)0.005 (3)
C330.034 (3)0.036 (3)0.051 (4)−0.001 (3)0.010 (3)−0.007 (3)
C340.051 (4)0.036 (3)0.049 (4)−0.003 (3)0.006 (3)−0.010 (3)
C350.058 (5)0.041 (4)0.052 (5)−0.021 (3)0.001 (4)−0.002 (4)
C360.052 (5)0.069 (5)0.070 (6)−0.026 (4)0.026 (4)−0.007 (5)
C370.049 (4)0.057 (4)0.059 (5)−0.012 (4)0.028 (4)−0.006 (4)
C380.029 (3)0.034 (3)0.033 (3)−0.002 (2)0.011 (3)−0.003 (3)
C390.040 (4)0.043 (4)0.040 (4)0.002 (3)0.013 (3)−0.003 (3)
C400.055 (4)0.058 (5)0.044 (4)−0.003 (4)0.019 (4)−0.018 (4)
C410.054 (5)0.076 (6)0.033 (4)−0.005 (4)0.015 (3)−0.003 (4)
C420.066 (5)0.061 (5)0.042 (4)−0.008 (4)0.021 (4)0.013 (4)
C430.054 (4)0.033 (3)0.044 (4)−0.001 (3)0.025 (3)0.002 (3)

Geometric parameters (Å, °)

Au1—P12.2582 (15)C14—C151.378 (12)
Au1—S12.3087 (16)C15—C161.381 (11)
Au2—P22.2421 (15)C15—H150.9400
Au2—S22.3012 (16)C16—H160.9400
Au1—Au23.2320 (5)C17—C181.479 (11)
S1—C11.759 (8)C17—H17A0.9800
S2—C101.761 (7)C17—H17B0.9800
P1—C201.815 (6)C18—H18A0.9700
P1—C261.816 (6)C18—H18B0.9700
P1—C191.839 (6)C18—H18C0.9700
P2—C381.808 (6)C19—H19A0.9800
P2—C321.826 (6)C19—H19B0.9800
P2—C191.831 (6)C20—C211.377 (8)
O2—N21.224 (8)C20—C251.399 (8)
O3—N21.213 (8)C21—C221.366 (9)
O4—C101.364 (7)C21—H210.9400
O4—C171.468 (9)C22—C231.376 (10)
O5—N41.215 (11)C22—H220.9400
O6—N41.215 (11)C23—C241.381 (9)
N1—C11.264 (9)C23—H230.9400
N1—C21.397 (8)C24—C251.383 (9)
N2—C51.470 (8)C24—H240.9400
N3—C101.249 (8)C25—H250.9400
N3—C111.405 (9)C26—C311.389 (9)
N4—C141.446 (9)C26—C271.410 (9)
C1—O1A1.35 (4)C27—C281.368 (10)
C1—O11.377 (14)C27—H270.9400
C2—C31.391 (10)C28—C291.346 (12)
C2—C71.392 (10)C28—H280.9400
C3—C41.382 (9)C29—C301.387 (11)
C3—H30.9400C29—H290.9400
C4—C51.384 (9)C30—C311.395 (9)
C4—H40.9400C30—H300.9400
C5—C61.391 (9)C31—H310.9400
C6—C71.371 (9)C32—C371.371 (9)
C6—H60.9400C32—C331.381 (9)
C7—H70.9400C33—C341.396 (9)
O1—C81.465 (9)C33—H330.9400
C8—C91.473 (10)C34—C351.368 (10)
C8—H8A0.9800C34—H340.9400
C8—H8B0.9800C35—C361.347 (11)
C9—H9A0.9700C35—H350.9400
C9—H9B0.9700C36—C371.394 (10)
C9—H9C0.9700C36—H360.9400
O1A—C8A1.455 (10)C37—H370.9400
C8A—C9A1.478 (10)C38—C391.383 (9)
C8A—H8C0.9800C38—C431.394 (9)
C8A—H8D0.9800C39—C401.390 (10)
C9A—H9D0.9700C39—H390.9400
C9A—H9E0.9700C40—C411.362 (11)
C9A—H9F0.9700C40—H400.9400
C11—C121.395 (10)C41—C421.393 (11)
C11—C161.416 (11)C41—H410.9400
C12—C131.376 (10)C42—C431.396 (10)
C12—H120.9400C42—H420.9400
C13—C141.365 (11)C43—H430.9400
C13—H130.9400
P1—Au1—S1172.77 (6)C15—C16—H16120.1
P1—Au1—Au288.36 (4)C11—C16—H16120.1
S1—Au1—Au298.86 (4)O4—C17—C18107.7 (7)
P2—Au2—S2173.84 (6)O4—C17—H17A110.2
P2—Au2—Au180.42 (4)C18—C17—H17A110.2
S2—Au2—Au1104.74 (4)O4—C17—H17B110.2
C1—S1—Au1102.4 (2)C18—C17—H17B110.2
C10—S2—Au2100.7 (2)H17A—C17—H17B108.5
C20—P1—C26106.9 (3)C17—C18—H18A109.5
C20—P1—C19105.3 (3)C17—C18—H18B109.5
C26—P1—C19104.7 (3)H18A—C18—H18B109.5
C20—P1—Au1111.07 (19)C17—C18—H18C109.5
C26—P1—Au1112.6 (2)H18A—C18—H18C109.5
C19—P1—Au1115.60 (19)H18B—C18—H18C109.5
C38—P2—C32107.0 (3)P2—C19—P1110.1 (3)
C38—P2—C19106.5 (3)P2—C19—H19A109.6
C32—P2—C19105.1 (3)P1—C19—H19A109.6
C38—P2—Au2115.44 (19)P2—C19—H19B109.6
C32—P2—Au2111.7 (2)P1—C19—H19B109.6
C19—P2—Au2110.46 (19)H19A—C19—H19B108.2
C10—O4—C17116.5 (5)C21—C20—C25118.9 (6)
C1—N1—C2122.7 (6)C21—C20—P1119.3 (5)
O3—N2—O2122.6 (6)C25—C20—P1121.8 (4)
O3—N2—C5118.8 (6)C22—C21—C20120.6 (6)
O2—N2—C5118.6 (6)C22—C21—H21119.7
C10—N3—C11121.0 (6)C20—C21—H21119.7
O6—N4—O5122.9 (8)C21—C22—C23120.5 (6)
O6—N4—C14120.2 (10)C21—C22—H22119.7
O5—N4—C14116.9 (9)C23—C22—H22119.7
N1—C1—O1A117.8 (14)C22—C23—C24120.3 (6)
N1—C1—O1120.2 (8)C22—C23—H23119.9
O1A—C1—O124.6 (12)C24—C23—H23119.9
N1—C1—S1125.9 (5)C23—C24—C25119.2 (6)
O1A—C1—S1114.1 (14)C23—C24—H24120.4
O1—C1—S1113.3 (7)C25—C24—H24120.4
C3—C2—C7118.3 (6)C24—C25—C20120.5 (6)
C3—C2—N1122.0 (7)C24—C25—H25119.8
C7—C2—N1119.4 (7)C20—C25—H25119.8
C4—C3—C2121.6 (6)C31—C26—C27120.2 (6)
C4—C3—H3119.2C31—C26—P1120.8 (5)
C2—C3—H3119.2C27—C26—P1119.0 (5)
C3—C4—C5117.8 (6)C28—C27—C26119.2 (7)
C3—C4—H4121.1C28—C27—H27120.4
C5—C4—H4121.1C26—C27—H27120.4
C4—C5—C6122.5 (6)C29—C28—C27121.4 (8)
C4—C5—N2118.9 (6)C29—C28—H28119.3
C6—C5—N2118.6 (6)C27—C28—H28119.3
C7—C6—C5117.9 (6)C28—C29—C30120.4 (7)
C7—C6—H6121.1C28—C29—H29119.8
C5—C6—H6121.1C30—C29—H29119.8
C6—C7—C2121.9 (6)C29—C30—C31120.4 (7)
C6—C7—H7119.1C29—C30—H30119.8
C2—C7—H7119.1C31—C30—H30119.8
C1—O1—C8115.3 (12)C26—C31—C30118.3 (7)
O1—C8—C9110.1 (17)C26—C31—H31120.8
O1—C8—H8A109.6C30—C31—H31120.8
C9—C8—H8A109.6C37—C32—C33119.6 (6)
O1—C8—H8B109.6C37—C32—P2118.7 (5)
C9—C8—H8B109.6C33—C32—P2121.5 (5)
H8A—C8—H8B108.1C32—C33—C34119.0 (6)
C1—O1A—C8A123 (3)C32—C33—H33120.5
O1A—C8A—C9A110 (4)C34—C33—H33120.5
O1A—C8A—H8C109.7C35—C34—C33120.7 (7)
C9A—C8A—H8C109.7C35—C34—H34119.7
O1A—C8A—H8D109.7C33—C34—H34119.7
C9A—C8A—H8D109.7C36—C35—C34120.1 (7)
H8C—C8A—H8D108.2C36—C35—H35119.9
C8A—C9A—H9D109.5C34—C35—H35119.9
C8A—C9A—H9E109.5C35—C36—C37120.3 (7)
H9D—C9A—H9E109.5C35—C36—H36119.8
C8A—C9A—H9F109.5C37—C36—H36119.8
H9D—C9A—H9F109.5C32—C37—C36120.2 (7)
H9E—C9A—H9F109.5C32—C37—H37119.9
N3—C10—O4121.2 (6)C36—C37—H37119.9
N3—C10—S2125.3 (5)C39—C38—C43119.4 (6)
O4—C10—S2113.5 (5)C39—C38—P2120.8 (5)
C12—C11—N3120.0 (7)C43—C38—P2119.8 (5)
C12—C11—C16119.5 (7)C38—C39—C40120.9 (7)
N3—C11—C16120.2 (7)C38—C39—H39119.6
C13—C12—C11120.1 (7)C40—C39—H39119.6
C13—C12—H12120.0C41—C40—C39119.9 (7)
C11—C12—H12120.0C41—C40—H40120.0
C14—C13—C12119.2 (7)C39—C40—H40120.0
C14—C13—H13120.4C40—C41—C42120.4 (7)
C12—C13—H13120.4C40—C41—H41119.8
C13—C14—C15123.0 (7)C42—C41—H41119.8
C13—C14—N4119.9 (8)C41—C42—C43120.0 (7)
C15—C14—N4117.2 (8)C41—C42—H42120.0
C14—C15—C16118.5 (8)C43—C42—H42120.0
C14—C15—H15120.8C38—C43—C42119.4 (7)
C16—C15—H15120.8C38—C43—H43120.3
C15—C16—C11119.8 (8)C42—C43—H43120.3
P1—Au1—Au2—P228.86 (6)N4—C14—C15—C16−176.7 (7)
S1—Au1—Au2—P2−151.57 (7)C14—C15—C16—C11−2.6 (12)
P1—Au1—Au2—S2−147.71 (6)C12—C11—C16—C151.6 (11)
S1—Au1—Au2—S231.86 (7)N3—C11—C16—C15175.0 (7)
P1—Au1—S1—C1−22.7 (6)C10—O4—C17—C18176.7 (8)
Au2—Au1—S1—C1160.7 (3)C38—P2—C19—P1−58.8 (4)
P2—Au2—S2—C1022.0 (7)C32—P2—C19—P1−172.1 (3)
Au1—Au2—S2—C10168.6 (2)Au2—P2—C19—P167.2 (3)
S1—Au1—P1—C20−59.6 (6)C20—P1—C19—P2−155.5 (3)
Au2—Au1—P1—C20117.0 (2)C26—P1—C19—P292.0 (3)
S1—Au1—P1—C2660.2 (6)Au1—P1—C19—P2−32.5 (4)
Au2—Au1—P1—C26−123.2 (2)C26—P1—C20—C21−106.5 (5)
S1—Au1—P1—C19−180 (100)C19—P1—C20—C21142.6 (5)
Au2—Au1—P1—C19−2.9 (2)Au1—P1—C20—C2116.7 (5)
S2—Au2—P2—C38−145.2 (6)C26—P1—C20—C2572.4 (5)
Au1—Au2—P2—C3867.5 (2)C19—P1—C20—C25−38.6 (6)
S2—Au2—P2—C32−22.6 (6)Au1—P1—C20—C25−164.4 (4)
Au1—Au2—P2—C32−170.0 (2)C25—C20—C21—C220.0 (9)
S2—Au2—P2—C1994.0 (6)P1—C20—C21—C22178.8 (5)
Au1—Au2—P2—C19−53.4 (2)C20—C21—C22—C230.5 (10)
C2—N1—C1—O1A−158.0 (15)C21—C22—C23—C24−0.9 (11)
C2—N1—C1—O1173.9 (10)C22—C23—C24—C250.8 (11)
C2—N1—C1—S14.2 (13)C23—C24—C25—C20−0.3 (10)
Au1—S1—C1—N1171.7 (8)C21—C20—C25—C24−0.1 (10)
Au1—S1—C1—O1A−25.6 (14)P1—C20—C25—C24−178.9 (5)
Au1—S1—C1—O11.4 (9)C20—P1—C26—C31−66.9 (6)
C1—N1—C2—C363.0 (12)C19—P1—C26—C3144.5 (6)
C1—N1—C2—C7−123.0 (9)Au1—P1—C26—C31170.8 (4)
C7—C2—C3—C4−0.2 (11)C20—P1—C26—C27114.3 (5)
N1—C2—C3—C4173.8 (7)C19—P1—C26—C27−134.4 (5)
C2—C3—C4—C50.3 (11)Au1—P1—C26—C27−8.0 (6)
C3—C4—C5—C6−0.6 (10)C31—C26—C27—C28−0.5 (10)
C3—C4—C5—N2−179.1 (6)P1—C26—C27—C28178.3 (6)
O3—N2—C5—C4−169.8 (6)C26—C27—C28—C29−0.6 (12)
O2—N2—C5—C49.5 (10)C27—C28—C29—C300.8 (12)
O3—N2—C5—C611.7 (10)C28—C29—C30—C310.1 (11)
O2—N2—C5—C6−169.1 (6)C27—C26—C31—C301.4 (9)
C4—C5—C6—C70.9 (10)P1—C26—C31—C30−177.4 (5)
N2—C5—C6—C7179.4 (6)C29—C30—C31—C26−1.3 (10)
C5—C6—C7—C2−0.8 (10)C38—P2—C32—C3750.4 (6)
C3—C2—C7—C60.5 (10)C19—P2—C32—C37163.3 (6)
N1—C2—C7—C6−173.7 (7)Au2—P2—C32—C37−76.9 (6)
N1—C1—O1—C811.6 (19)C38—P2—C32—C33−133.3 (5)
O1A—C1—O1—C8−80 (4)C19—P2—C32—C33−20.4 (6)
S1—C1—O1—C8−177.5 (11)Au2—P2—C32—C3399.4 (5)
C1—O1—C8—C976.0 (19)C37—C32—C33—C340.9 (10)
N1—C1—O1A—C8A−10 (4)P2—C32—C33—C34−175.3 (5)
O1—C1—O1A—C8A93 (5)C32—C33—C34—C350.0 (11)
S1—C1—O1A—C8A−174 (2)C33—C34—C35—C36−0.9 (12)
C1—O1A—C8A—C9A−74 (4)C34—C35—C36—C370.9 (13)
C11—N3—C10—O4−177.3 (7)C33—C32—C37—C36−1.0 (11)
C11—N3—C10—S22.8 (12)P2—C32—C37—C36175.4 (6)
C17—O4—C10—N3−0.6 (11)C35—C36—C37—C320.1 (13)
C17—O4—C10—S2179.3 (6)C32—P2—C38—C39−134.5 (5)
Au2—S2—C10—N3161.0 (7)C19—P2—C38—C39113.6 (5)
Au2—S2—C10—O4−18.9 (6)Au2—P2—C38—C39−9.4 (6)
C10—N3—C11—C12−104.3 (9)C32—P2—C38—C4349.2 (6)
C10—N3—C11—C1682.4 (10)C19—P2—C38—C43−62.8 (5)
N3—C11—C12—C13−174.0 (6)Au2—P2—C38—C43174.2 (4)
C16—C11—C12—C13−0.6 (11)C43—C38—C39—C400.4 (10)
C11—C12—C13—C140.7 (11)P2—C38—C39—C40−176.0 (5)
C12—C13—C14—C15−1.8 (12)C38—C39—C40—C410.8 (11)
C12—C13—C14—N4177.7 (7)C39—C40—C41—C42−1.6 (12)
O6—N4—C14—C13169.9 (8)C40—C41—C42—C431.1 (12)
O5—N4—C14—C13−11.0 (11)C39—C38—C43—C42−0.9 (10)
O6—N4—C14—C15−10.6 (11)P2—C38—C43—C42175.5 (5)
O5—N4—C14—C15168.5 (8)C41—C42—C43—C380.1 (11)
C13—C14—C15—C162.7 (12)

Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C2–C7 and C38–C43 rings, respectively.
D—H···AD—HH···AD···AD—H···A
C41—H41···Cg1i0.942.733.576 (8)151
C17—H17b···Cg2ii0.982.873.821 (11)163

Symmetry codes: (i) −x+2, −y+2, −z+1; (ii) −x+3/2, −y+3/2, −z+1/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB5435).

References

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  • Hall, V. J., Siasios, G. & Tiekink, E. R. T. (1993). Aust. J. Chem.46, 561–570.
  • Ho, S. Y., Cheng, E. C.-C., Tiekink, E. R. T. & Yam, V. W.-W. (2006). Inorg. Chem.45, 8165–8174. [PubMed]
  • Ho, S. Y. & Tiekink, E. R. T. (2007). CrystEngComm, 9, 368–378.
  • Kuan, F. S., Ho, S. Y., Tadbuppa, P. P. & Tiekink, E. R. T. (2008). CrystEngComm, 10, 548–564.
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  • Westrip, S. P. (2010). J. Appl. Cryst.43 Submitted.

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