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Acta Crystallogr Sect E Struct Rep Online. 2010 April 1; 66(Pt 4): m420.
Published online 2010 March 20. doi:  10.1107/S1600536810009736
PMCID: PMC2983867

[(Z)-O-Isopropyl N-(4-chloro­phen­yl)thio­carbamato-κS](tricyclo­hexyl­phosphine-κP)gold(I)

Abstract

The Au atom in the title compound, [Au(C10H11ClNOS)(C18H33P)], is coordinated within an S,P-donor set that defines a slightly distorted linear geometry [S—Au—P = 172.45 (5)°], with the distortion due in part to a close intra­molecular Au(...)O contact [3.134 (3) Å].

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]).

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Object name is e-66-0m420-scheme1.jpg

Experimental

Crystal data

  • [Au(C10H11ClNOS)(C18H33P)]
  • M r = 706.09
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-0m420-efi1.jpg
  • a = 9.4547 (15) Å
  • b = 26.137 (4) Å
  • c = 12.326 (2) Å
  • β = 100.162 (3)°
  • V = 2998.0 (8) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 5.14 mm−1
  • T = 223 K
  • 0.32 × 0.07 × 0.07 mm

Data collection

  • Bruker SMART CCD diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2000 [triangle]) T min = 0.466, T max = 1.000
  • 20961 measured reflections
  • 6886 independent reflections
  • 5416 reflections with I > 2σ(I)
  • R int = 0.037

Refinement

  • R[F 2 > 2σ(F 2)] = 0.039
  • wR(F 2) = 0.087
  • S = 1.06
  • 6886 reflections
  • 307 parameters
  • H-atom parameters constrained
  • Δρmax = 3.49 e Å−3
  • Δρmin = −1.06 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)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810009736/hg2659sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810009736/hg2659Isup2.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

Crystal engineering and luminescence imperatives motivated systematic studies of R3PAu[SC(OR')═NR''], for R, R' and R'' = alkyl and aryl, derivatives (Ho et al. 2006; Ho & Tiekink, 2007; Kuan et al., 2008). The synthesis and characterisation of the title compound, (I), was investigated in this context.

The gold atom in (I) exists within an SP donor set defined by the phosphine-P and thiolate-S atoms, Table 1 and Fig. 1. The carbonimidothioate ligand is functioning as a thiolate as seen by the magnitudes of the C1—S1 [1.750 (5) Å] and C1═N1 [1.257 (6) Å] bond distances. The coordination geometry is distorted from the ideal linear [S—Au—P = 172.45 (5) °] owing to the close approach of the O1 atom [3.134 (3) Å]. 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 (i-Pr)OC(═S)N(H)(C6H4Cl-4) 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). The maximum and minimum residual electron density peaks of 3.49 and 1.06 e Å-3, respectively, were located 0.85 Å and 0.70 Å from the Au atom.

Figures

Fig. 1.
Molecular structure of (I) showing atom-labelling scheme and displacement ellipsoids at the 35% probability level.

Crystal data

[Au(C10H11ClNOS)(C18H33P)]F(000) = 1416
Mr = 706.09Dx = 1.564 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71069 Å
Hall symbol: -P 2ybcCell parameters from 879 reflections
a = 9.4547 (15) Åθ = 2.6–27.4°
b = 26.137 (4) ŵ = 5.14 mm1
c = 12.326 (2) ÅT = 223 K
β = 100.162 (3)°Prism, colourless
V = 2998.0 (8) Å30.32 × 0.07 × 0.07 mm
Z = 4

Data collection

Bruker SMART CCD diffractometer6886 independent reflections
Radiation source: fine-focus sealed tube5416 reflections with I > 2σ(I)
graphiteRint = 0.037
ω scansθmax = 27.5°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2000)h = −12→9
Tmin = 0.466, Tmax = 1.000k = −33→33
20961 measured reflectionsl = −15→15

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) = 0.087H-atom parameters constrained
S = 1.06w = 1/[σ2(Fo2) + (0.0354P)2 + 3.2652P] where P = (Fo2 + 2Fc2)/3
6886 reflections(Δ/σ)max = 0.001
307 parametersΔρmax = 3.49 e Å3
0 restraintsΔρmin = −1.06 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
Au0.11172 (2)0.032224 (6)0.326336 (15)0.03900 (7)
Cl1−0.41157 (16)0.29686 (6)0.41611 (13)0.0629 (4)
S10.04148 (19)0.11519 (5)0.35057 (11)0.0547 (4)
P10.16119 (15)−0.05231 (5)0.31795 (10)0.0361 (3)
O10.1788 (4)0.12683 (12)0.1876 (3)0.0391 (8)
N10.0218 (5)0.19166 (14)0.2031 (3)0.0398 (9)
C10.0788 (5)0.14992 (17)0.2375 (4)0.0360 (10)
C2−0.0798 (5)0.21535 (17)0.2577 (4)0.0365 (11)
C3−0.0419 (6)0.23739 (19)0.3612 (4)0.0445 (12)
H30.05370.23510.39820.053*
C4−0.1416 (6)0.26265 (19)0.4109 (4)0.0431 (12)
H4−0.11490.27710.48130.052*
C5−0.2805 (5)0.26620 (17)0.3554 (4)0.0396 (11)
C6−0.3205 (6)0.2456 (2)0.2522 (4)0.0478 (13)
H6−0.41570.24870.21470.057*
C7−0.2198 (6)0.2204 (2)0.2044 (4)0.0468 (12)
H7−0.24700.20630.13360.056*
C80.2135 (6)0.1506 (2)0.0885 (4)0.0443 (12)
H80.12400.16100.03900.053*
C90.3096 (7)0.1964 (2)0.1161 (6)0.0720 (19)
H9A0.25810.22290.14830.108*
H9B0.33820.20930.04940.108*
H9C0.39430.18650.16830.108*
C100.2859 (7)0.1079 (2)0.0358 (5)0.0570 (15)
H10A0.21910.07980.01770.085*
H10B0.36960.09620.08690.085*
H10C0.31530.1205−0.03090.085*
C110.2157 (5)−0.07089 (17)0.1873 (4)0.0357 (10)
H110.2373−0.10800.18980.043*
C120.3503 (6)−0.0418 (2)0.1728 (4)0.0467 (13)
H12A0.4278−0.04960.23460.056*
H12B0.3313−0.00490.17390.056*
C130.3983 (7)−0.0558 (2)0.0650 (5)0.0594 (16)
H13A0.4813−0.03470.05620.071*
H13B0.4286−0.09170.06780.071*
C140.2799 (8)−0.0479 (2)−0.0335 (5)0.0689 (19)
H14A0.3116−0.0610−0.09980.083*
H14B0.2610−0.0112−0.04380.083*
C150.1423 (7)−0.0750 (2)−0.0190 (5)0.0618 (16)
H15A0.0655−0.0660−0.08040.074*
H15B0.1569−0.1121−0.02060.074*
C160.0970 (6)−0.0603 (2)0.0886 (4)0.0496 (13)
H16A0.0108−0.07970.09700.059*
H16B0.0725−0.02390.08700.059*
C170.3117 (6)−0.07052 (19)0.4301 (4)0.0465 (12)
H170.3989−0.05540.40900.056*
C180.2971 (7)−0.0452 (2)0.5377 (5)0.0554 (14)
H18A0.2907−0.00810.52710.066*
H18B0.2080−0.05680.56020.066*
C190.4528 (8)−0.1131 (3)0.6415 (7)0.083 (2)
H19A0.5414−0.11800.69530.100*
H19B0.3744−0.12980.67060.100*
C200.4219 (8)−0.0573 (3)0.6277 (5)0.0724 (19)
H20A0.5077−0.04000.61140.087*
H20B0.4020−0.04350.69740.087*
C210.4688 (8)−0.1377 (3)0.5361 (6)0.079 (2)
H21A0.4788−0.17470.54750.095*
H21B0.5573−0.12520.51410.095*
C220.3425 (6)−0.1274 (2)0.4425 (5)0.0572 (15)
H22A0.3649−0.14100.37330.069*
H22B0.2569−0.14520.45790.069*
C230.0073 (6)−0.09140 (18)0.3403 (5)0.0458 (12)
H230.0199−0.09580.42120.055*
C24−0.0029 (6)−0.14566 (19)0.2938 (5)0.0493 (13)
H24A−0.0203−0.14420.21310.059*
H24B0.0883−0.16350.31820.059*
C25−0.1236 (7)−0.1750 (2)0.3320 (6)0.0714 (19)
H25A−0.1305−0.20900.29800.086*
H25B−0.0997−0.17970.41200.086*
C26−0.2653 (7)−0.1494 (2)0.3048 (6)0.0650 (17)
H26A−0.3351−0.16800.34010.078*
H26B−0.2985−0.15060.22490.078*
C27−0.2580 (6)−0.0941 (2)0.3430 (5)0.0571 (15)
H27A−0.3490−0.07720.31290.068*
H27B−0.2470−0.09330.42360.068*
C28−0.1359 (6)−0.0642 (2)0.3087 (5)0.0548 (14)
H28A−0.1299−0.03040.34370.066*
H28B−0.1561−0.05910.22870.066*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Au0.05318 (13)0.02822 (10)0.03867 (11)0.00624 (9)0.01655 (8)0.00351 (8)
Cl10.0515 (9)0.0689 (9)0.0713 (10)0.0156 (7)0.0188 (7)−0.0129 (8)
S10.0946 (12)0.0329 (6)0.0458 (7)0.0167 (7)0.0377 (8)0.0081 (5)
P10.0430 (7)0.0294 (6)0.0383 (7)0.0035 (5)0.0137 (6)0.0014 (5)
O10.046 (2)0.0363 (17)0.0385 (18)0.0048 (15)0.0171 (16)0.0017 (14)
N10.048 (3)0.036 (2)0.039 (2)0.0080 (18)0.0156 (19)0.0063 (17)
C10.044 (3)0.032 (2)0.034 (2)−0.003 (2)0.012 (2)0.0011 (19)
C20.045 (3)0.030 (2)0.038 (3)0.003 (2)0.017 (2)0.0041 (19)
C30.040 (3)0.046 (3)0.046 (3)0.006 (2)0.002 (2)0.001 (2)
C40.046 (3)0.043 (3)0.040 (3)0.005 (2)0.008 (2)−0.005 (2)
C50.038 (3)0.035 (2)0.047 (3)0.006 (2)0.013 (2)−0.001 (2)
C60.040 (3)0.052 (3)0.050 (3)0.003 (2)0.006 (2)0.000 (2)
C70.048 (3)0.051 (3)0.041 (3)−0.002 (2)0.008 (2)−0.006 (2)
C80.046 (3)0.051 (3)0.039 (3)0.008 (2)0.017 (2)0.009 (2)
C90.069 (4)0.053 (4)0.105 (6)−0.006 (3)0.044 (4)0.005 (4)
C100.058 (4)0.068 (4)0.049 (3)0.015 (3)0.022 (3)−0.003 (3)
C110.038 (3)0.031 (2)0.040 (3)0.000 (2)0.015 (2)−0.0033 (19)
C120.044 (3)0.050 (3)0.047 (3)−0.004 (2)0.013 (3)0.004 (2)
C130.065 (4)0.052 (3)0.072 (4)0.002 (3)0.040 (4)0.005 (3)
C140.108 (6)0.057 (3)0.052 (4)0.001 (4)0.043 (4)0.003 (3)
C150.085 (5)0.062 (4)0.039 (3)−0.014 (3)0.011 (3)−0.009 (3)
C160.045 (3)0.063 (3)0.039 (3)−0.005 (3)0.001 (2)−0.004 (2)
C170.052 (3)0.042 (3)0.045 (3)0.006 (2)0.006 (2)0.007 (2)
C180.059 (4)0.052 (3)0.052 (3)0.003 (3)0.002 (3)−0.003 (3)
C190.067 (5)0.096 (6)0.079 (5)−0.004 (4)−0.009 (4)0.029 (4)
C200.079 (5)0.088 (5)0.044 (3)−0.014 (4)−0.007 (3)0.010 (3)
C210.073 (5)0.076 (5)0.087 (5)0.027 (4)0.011 (4)0.035 (4)
C220.053 (4)0.040 (3)0.076 (4)0.004 (3)0.006 (3)0.002 (3)
C230.050 (3)0.036 (2)0.055 (3)−0.001 (2)0.018 (3)0.000 (2)
C240.049 (3)0.039 (3)0.063 (4)−0.005 (2)0.018 (3)−0.009 (2)
C250.075 (5)0.046 (3)0.103 (6)−0.011 (3)0.042 (4)−0.004 (3)
C260.051 (4)0.076 (4)0.068 (4)−0.020 (3)0.010 (3)−0.010 (3)
C270.047 (3)0.059 (3)0.070 (4)0.010 (3)0.024 (3)0.009 (3)
C280.037 (3)0.049 (3)0.077 (4)0.000 (2)0.005 (3)−0.004 (3)

Geometric parameters (Å, °)

Au—P12.2646 (12)C14—H14B0.9800
Au—S12.3027 (13)C15—C161.514 (7)
Cl1—C51.751 (5)C15—H15A0.9800
S1—C11.750 (5)C15—H15B0.9800
P1—C231.838 (5)C16—H16A0.9800
P1—C111.840 (4)C16—H16B0.9800
P1—C171.862 (5)C17—C181.511 (8)
O1—C11.356 (5)C17—C221.518 (7)
O1—C81.459 (5)C17—H170.9900
N1—C11.257 (6)C18—C201.503 (8)
N1—C21.410 (6)C18—H18A0.9800
C2—C71.376 (7)C18—H18B0.9800
C2—C31.388 (7)C19—C211.481 (10)
C3—C41.380 (7)C19—C201.492 (10)
C3—H30.9400C19—H19A0.9800
C4—C51.373 (7)C19—H19B0.9800
C4—H40.9400C20—H20A0.9800
C5—C61.371 (7)C20—H20B0.9800
C6—C71.374 (7)C21—C221.531 (9)
C6—H60.9400C21—H21A0.9800
C7—H70.9400C21—H21B0.9800
C8—C91.505 (8)C22—H22A0.9800
C8—C101.514 (7)C22—H22B0.9800
C8—H80.9900C23—C281.518 (7)
C9—H9A0.9700C23—C241.526 (7)
C9—H9B0.9700C23—H230.9900
C9—H9C0.9700C24—C251.516 (7)
C10—H10A0.9700C24—H24A0.9800
C10—H10B0.9700C24—H24B0.9800
C10—H10C0.9700C25—C261.481 (9)
C11—C121.520 (7)C25—H25A0.9800
C11—C161.528 (7)C25—H25B0.9800
C11—H110.9900C26—C271.519 (8)
C12—C131.524 (7)C26—H26A0.9800
C12—H12A0.9800C26—H26B0.9800
C12—H12B0.9800C27—C281.514 (7)
C13—C141.513 (9)C27—H27A0.9800
C13—H13A0.9800C27—H27B0.9800
C13—H13B0.9800C28—H28A0.9800
C14—C151.519 (9)C28—H28B0.9800
C14—H14A0.9800
P1—Au—S1172.45 (5)C15—C16—C11111.7 (5)
C1—S1—Au106.36 (16)C15—C16—H16A109.3
C23—P1—C11109.6 (2)C11—C16—H16A109.3
C23—P1—C17105.6 (2)C15—C16—H16B109.3
C11—P1—C17106.7 (2)C11—C16—H16B109.3
C23—P1—Au111.10 (16)H16A—C16—H16B107.9
C11—P1—Au112.92 (15)C18—C17—C22112.7 (5)
C17—P1—Au110.63 (17)C18—C17—P1111.3 (4)
C1—O1—C8117.9 (4)C22—C17—P1115.7 (4)
C1—N1—C2120.5 (4)C18—C17—H17105.4
N1—C1—O1121.7 (4)C22—C17—H17105.4
N1—C1—S1125.7 (4)P1—C17—H17105.4
O1—C1—S1112.6 (3)C20—C18—C17112.0 (5)
C7—C2—C3118.0 (4)C20—C18—H18A109.2
C7—C2—N1119.6 (4)C17—C18—H18A109.2
C3—C2—N1122.2 (5)C20—C18—H18B109.2
C4—C3—C2121.4 (5)C17—C18—H18B109.2
C4—C3—H3119.3H18A—C18—H18B107.9
C2—C3—H3119.3C21—C19—C20111.8 (6)
C5—C4—C3118.7 (5)C21—C19—H19A109.3
C5—C4—H4120.7C20—C19—H19A109.3
C3—C4—H4120.7C21—C19—H19B109.3
C6—C5—C4121.3 (5)C20—C19—H19B109.3
C6—C5—Cl1118.4 (4)H19A—C19—H19B107.9
C4—C5—Cl1120.4 (4)C19—C20—C18113.7 (6)
C5—C6—C7119.2 (5)C19—C20—H20A108.8
C5—C6—H6120.4C18—C20—H20A108.8
C7—C6—H6120.4C19—C20—H20B108.8
C6—C7—C2121.5 (5)C18—C20—H20B108.8
C6—C7—H7119.3H20A—C20—H20B107.7
C2—C7—H7119.3C19—C21—C22113.5 (6)
O1—C8—C9111.5 (5)C19—C21—H21A108.9
O1—C8—C10103.3 (4)C22—C21—H21A108.9
C9—C8—C10112.5 (5)C19—C21—H21B108.9
O1—C8—H8109.8C22—C21—H21B108.9
C9—C8—H8109.8H21A—C21—H21B107.7
C10—C8—H8109.8C17—C22—C21111.0 (5)
C8—C9—H9A109.5C17—C22—H22A109.4
C8—C9—H9B109.5C21—C22—H22A109.4
H9A—C9—H9B109.5C17—C22—H22B109.4
C8—C9—H9C109.5C21—C22—H22B109.4
H9A—C9—H9C109.5H22A—C22—H22B108.0
H9B—C9—H9C109.5C28—C23—C24110.1 (5)
C8—C10—H10A109.5C28—C23—P1113.3 (4)
C8—C10—H10B109.5C24—C23—P1117.3 (4)
H10A—C10—H10B109.5C28—C23—H23104.9
C8—C10—H10C109.5C24—C23—H23104.9
H10A—C10—H10C109.5P1—C23—H23104.9
H10B—C10—H10C109.5C25—C24—C23110.8 (4)
C12—C11—C16109.2 (4)C25—C24—H24A109.5
C12—C11—P1109.9 (3)C23—C24—H24A109.5
C16—C11—P1111.7 (3)C25—C24—H24B109.5
C12—C11—H11108.7C23—C24—H24B109.5
C16—C11—H11108.7H24A—C24—H24B108.1
P1—C11—H11108.7C26—C25—C24113.7 (5)
C11—C12—C13111.5 (4)C26—C25—H25A108.8
C11—C12—H12A109.3C24—C25—H25A108.8
C13—C12—H12A109.3C26—C25—H25B108.8
C11—C12—H12B109.3C24—C25—H25B108.8
C13—C12—H12B109.3H25A—C25—H25B107.7
H12A—C12—H12B108.0C25—C26—C27111.7 (5)
C14—C13—C12112.0 (5)C25—C26—H26A109.3
C14—C13—H13A109.2C27—C26—H26A109.3
C12—C13—H13A109.2C25—C26—H26B109.3
C14—C13—H13B109.2C27—C26—H26B109.3
C12—C13—H13B109.2H26A—C26—H26B107.9
H13A—C13—H13B107.9C28—C27—C26113.6 (5)
C13—C14—C15111.8 (5)C28—C27—H27A108.9
C13—C14—H14A109.3C26—C27—H27A108.9
C15—C14—H14A109.3C28—C27—H27B108.9
C13—C14—H14B109.3C26—C27—H27B108.9
C15—C14—H14B109.3H27A—C27—H27B107.7
H14A—C14—H14B107.9C27—C28—C23112.1 (5)
C16—C15—C14111.5 (5)C27—C28—H28A109.2
C16—C15—H15A109.3C23—C28—H28A109.2
C14—C15—H15A109.3C27—C28—H28B109.2
C16—C15—H15B109.3C23—C28—H28B109.2
C14—C15—H15B109.3H28A—C28—H28B107.9
H15A—C15—H15B108.0
P1—Au—S1—C1−159.3 (4)C12—C13—C14—C15−52.6 (7)
S1—Au—P1—C2329.2 (5)C13—C14—C15—C1653.0 (7)
S1—Au—P1—C11152.8 (4)C14—C15—C16—C11−56.1 (7)
S1—Au—P1—C17−87.8 (5)C12—C11—C16—C1557.6 (6)
C2—N1—C1—O1−178.8 (4)P1—C11—C16—C15179.3 (4)
C2—N1—C1—S11.4 (7)C23—P1—C17—C18−78.2 (4)
C8—O1—C1—N1−3.1 (7)C11—P1—C17—C18165.2 (4)
C8—O1—C1—S1176.7 (3)Au—P1—C17—C1842.1 (4)
Au—S1—C1—N1158.6 (4)C23—P1—C17—C2252.1 (5)
Au—S1—C1—O1−21.1 (4)C11—P1—C17—C22−64.4 (5)
C1—N1—C2—C7−114.7 (6)Au—P1—C17—C22172.4 (4)
C1—N1—C2—C370.2 (6)C22—C17—C18—C2051.2 (7)
C7—C2—C3—C41.5 (7)P1—C17—C18—C20−177.0 (4)
N1—C2—C3—C4176.7 (4)C21—C19—C20—C1852.5 (9)
C2—C3—C4—C5−0.7 (8)C17—C18—C20—C19−51.8 (8)
C3—C4—C5—C6−0.6 (8)C20—C19—C21—C22−52.7 (8)
C3—C4—C5—Cl1178.8 (4)C18—C17—C22—C21−50.9 (7)
C4—C5—C6—C70.9 (8)P1—C17—C22—C21179.4 (4)
Cl1—C5—C6—C7−178.6 (4)C19—C21—C22—C1752.1 (8)
C5—C6—C7—C20.1 (8)C11—P1—C23—C28−99.4 (4)
C3—C2—C7—C6−1.2 (7)C17—P1—C23—C28146.1 (4)
N1—C2—C7—C6−176.5 (5)Au—P1—C23—C2826.1 (5)
C1—O1—C8—C976.9 (6)C11—P1—C23—C2430.7 (5)
C1—O1—C8—C10−162.0 (4)C17—P1—C23—C24−83.8 (5)
C23—P1—C11—C12−175.4 (3)Au—P1—C23—C24156.2 (4)
C17—P1—C11—C12−61.6 (4)C28—C23—C24—C25−56.0 (7)
Au—P1—C11—C1260.1 (4)P1—C23—C24—C25172.5 (4)
C23—P1—C11—C1663.3 (4)C23—C24—C25—C2655.8 (8)
C17—P1—C11—C16177.1 (4)C24—C25—C26—C27−51.6 (8)
Au—P1—C11—C16−61.2 (4)C25—C26—C27—C2849.3 (8)
C16—C11—C12—C13−56.7 (6)C26—C27—C28—C23−51.7 (7)
P1—C11—C12—C13−179.5 (4)C24—C23—C28—C2754.6 (6)
C11—C12—C13—C1455.2 (6)P1—C23—C28—C27−171.8 (4)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HG2659).

References

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