metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2056-9890

[(Z)-O-Iso­propyl N-(m-tol­yl)thio­carbamato-κS](tri­cyclo­hexyl­phosphine-κP)gold(I)

aDepartment of Chemistry, National University of Singapore, Singapore 117543, and bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
*Correspondence e-mail: edward.tiekink@gmail.com

(Received 14 March 2010; accepted 15 March 2010; online 20 March 2010)

The Au atom in the title compound, [Au(C11H14NOS)(C18H33P)], is coordinated within an S,P-donor set that defines a slightly distorted linear geometry [S—Au—P = 174.73 (3)°], with the distortion due in part to a close intra­molecular Au⋯O contact [3.060 (3) Å]. In the crystal structure, mol­ecules are arranged in layers in the bc plane with the primary connections between the arrays being of the type C—H⋯π.

Related literature

For the structural systematics and luminescence properties of phosphinegold(I) carbonimidothio­ates, see: Ho et al. (2006[Ho, S. Y., Cheng, E. C.-C., Tiekink, E. R. T. & Yam, V. W.-W. (2006). Inorg. Chem. 45, 8165-8174.]); Ho & Tiekink (2007[Ho, S. Y. & Tiekink, E. R. T. (2007). CrystEngComm, 9, 368-378.]); Kuan et al. (2008[Kuan, F. S., Ho, S. Y., Tadbuppa, P. P. & Tiekink, E. R. T. (2008). CrystEngComm, 10, 548-564.]). For the synthesis, see Hall et al. (1993[Hall, V. J., Siasios, G. & Tiekink, E. R. T. (1993). Aust. J. Chem. 46, 561-570.]).

[Scheme 1]

Experimental

Crystal data
  • [Au(C11H14NOS)(C18H33P)]

  • Mr = 685.67

  • Monoclinic, P 21 /c

  • a = 13.7415 (18) Å

  • b = 13.3528 (18) Å

  • c = 16.788 (2) Å

  • β = 100.308 (3)°

  • V = 3030.7 (7) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 5.00 mm−1

  • T = 223 K

  • 0.37 × 0.10 × 0.10 mm

Data collection
  • Bruker SMART CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2000[Bruker (2000). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.445, Tmax = 1.000

  • 20885 measured reflections

  • 6943 independent reflections

  • 5710 reflections with I > 2σ(I)

  • Rint = 0.031

Refinement
  • R[F2 > 2σ(F2)] = 0.028

  • wR(F2) = 0.072

  • S = 1.03

  • 6943 reflections

  • 308 parameters

  • H-atom parameters constrained

  • Δρmax = 1.60 e Å−3

  • Δρmin = −0.40 e Å−3

Table 1
Selected bond lengths (Å)

Au—P1 2.2692 (9)
Au—S1 2.3051 (9)

Table 2
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C2–C7 ring.

D—H⋯A D—H H⋯A DA D—H⋯A
C16—H16a⋯Cgi 0.98 2.98 3.655 (5) 127
Symmetry code: (i) x-1, y, z.

Data collection: SMART (Bruker, 2000[Bruker (2000). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2000[Bruker (2000). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: PATTY in DIRDIF92 (Beurskens et al., 1992[Beurskens, P. T., Admiraal, G., Beurskens, G., Bosman, W. P., Garcia-Granda, S., Gould, R. O., Smits, J. M. M. & Smykalla, C. (1992). The DIRDIF Program System. Technical Report. Crystallography Laboratory, University of Nijmegen, The Netherlands.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]) and DIAMOND (Brandenburg, 2006[Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: publCIF (Westrip, 2010[Westrip, S. P. (2010). publCIF. In preparation.]).

Supporting information


Comment top

In the context of crystal engineering and luminescence 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), were investigated.

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 coordinating as a thiolate ligand as evidenced by the magnitudes of the C1—S1 [1.766 (4) Å] and C1N1 [1.266 (5) Å] bond distances. The coordination geometry is distorted from the ideal linear [S—Au—P = 174.73 (3) °] owing to the close approach of the O1 atom [3.060 (3) Å]. In the crystal structure, molecules forms layers in the ab plane with connections between the layers being of the type C–H···π, Table 2 and Fig. 2.

Related literature top

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

Experimental top

Compound (I) was prepared following the standard literature procedure from the reaction of Cy3PAuCl and (i-Pr)OC(S)N(H)(m-tolyl) 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 top

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 1.60 and 0.40 e Å-3, respectively, were located 0.84 Å and 1.53 Å from the Au atom.

Computing details top

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

Figures top
[Figure 1] Fig. 1. Molecular structure of (I) showing atom-labelling scheme and displacement ellipsoids at the 35% probability level.
[Figure 2] Fig. 2. A view of the unit cell contents of (I) shown in projection down the b axis with the C–H···π interactions shown as purple dashed lines. Colour code: Au, orange; S, yellow; P, pink; O, red; N, blue; C, grey; and H, green.
(I) top
Crystal data top
[Au(C11H14NOS)(C18H33P)]F(000) = 1384
Mr = 685.67Dx = 1.503 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71069 Å
Hall symbol: -P 2ybcCell parameters from 993 reflections
a = 13.7415 (18) Åθ = 2.4–26.7°
b = 13.3528 (18) ŵ = 5.00 mm1
c = 16.788 (2) ÅT = 223 K
β = 100.308 (3)°Block, colourless
V = 3030.7 (7) Å30.37 × 0.10 × 0.10 mm
Z = 4
Data collection top
Bruker SMART CCD
diffractometer
6943 independent reflections
Radiation source: fine-focus sealed tube5710 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.031
ω scansθmax = 27.5°, θmin = 1.5°
Absorption correction: multi-scan
(SADABS; Bruker, 2000)
h = 1717
Tmin = 0.445, Tmax = 1.000k = 1217
20885 measured reflectionsl = 2120
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.028Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.072H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.0386P)2]
where P = (Fo2 + 2Fc2)/3
6943 reflections(Δ/σ)max = 0.001
308 parametersΔρmax = 1.60 e Å3
0 restraintsΔρmin = 0.40 e Å3
Crystal data top
[Au(C11H14NOS)(C18H33P)]V = 3030.7 (7) Å3
Mr = 685.67Z = 4
Monoclinic, P21/cMo Kα radiation
a = 13.7415 (18) ŵ = 5.00 mm1
b = 13.3528 (18) ÅT = 223 K
c = 16.788 (2) Å0.37 × 0.10 × 0.10 mm
β = 100.308 (3)°
Data collection top
Bruker SMART CCD
diffractometer
6943 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2000)
5710 reflections with I > 2σ(I)
Tmin = 0.445, Tmax = 1.000Rint = 0.031
20885 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0280 restraints
wR(F2) = 0.072H-atom parameters constrained
S = 1.03Δρmax = 1.60 e Å3
6943 reflectionsΔρmin = 0.40 e Å3
308 parameters
Special details top

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) top
xyzUiso*/Ueq
Au0.009245 (9)0.077062 (9)0.342984 (7)0.03840 (5)
S10.16091 (6)0.15458 (6)0.37674 (6)0.0453 (2)
P10.13794 (6)0.00461 (6)0.32160 (5)0.03605 (18)
O10.19821 (19)0.00020 (18)0.29116 (16)0.0534 (6)
N10.3294 (2)0.1077 (2)0.3217 (2)0.0532 (8)
C10.2414 (3)0.0848 (2)0.3270 (2)0.0460 (8)
C20.3764 (2)0.1942 (3)0.3601 (3)0.0531 (9)
C30.3875 (3)0.2088 (3)0.4421 (3)0.0581 (10)
H30.35940.16280.47380.070*
C40.4409 (3)0.2924 (4)0.4799 (3)0.0660 (11)
C50.4820 (3)0.3578 (3)0.4314 (4)0.0733 (13)
H50.51760.41370.45490.088*
C60.4720 (3)0.3428 (4)0.3502 (3)0.0733 (13)
H60.50050.38830.31840.088*
C70.4203 (3)0.2612 (3)0.3142 (3)0.0640 (11)
H70.41480.25090.25820.077*
C80.4511 (4)0.3060 (5)0.5685 (3)0.0981 (17)
H8A0.51650.33170.59010.147*
H8B0.44180.24220.59370.147*
H8C0.40160.35310.57980.147*
C90.2533 (3)0.0593 (3)0.2416 (3)0.0610 (11)
H90.28940.01420.21020.073*
C100.1759 (4)0.1171 (4)0.1845 (3)0.0847 (15)
H10A0.13170.07060.15150.127*
H10B0.13840.15870.21550.127*
H10C0.20800.15920.14980.127*
C110.3256 (4)0.1286 (4)0.2928 (3)0.0811 (14)
H11A0.37550.08930.32750.122*
H11B0.35720.17080.25790.122*
H11C0.29070.17010.32580.122*
C120.2309 (3)0.0592 (2)0.3696 (2)0.0421 (8)
H120.24840.12160.33840.050*
C130.1880 (3)0.0913 (3)0.4560 (2)0.0511 (9)
H13A0.12820.13120.45580.061*
H13B0.16920.03160.48920.061*
C140.2617 (3)0.1526 (3)0.4934 (3)0.0649 (11)
H14A0.23300.16860.54970.078*
H14B0.27520.21580.46380.078*
C150.3573 (3)0.0959 (4)0.4909 (3)0.0715 (13)
H15A0.40480.13840.51210.086*
H15B0.34490.03650.52560.086*
C160.4009 (3)0.0637 (4)0.4053 (3)0.0778 (14)
H16A0.42000.12320.37190.093*
H16B0.46060.02380.40600.093*
C170.3273 (2)0.0023 (3)0.3681 (3)0.0568 (10)
H17A0.31350.06060.39820.068*
H17B0.35630.01440.31200.068*
C180.1932 (2)0.0195 (2)0.21456 (19)0.0404 (7)
H180.25010.06590.21100.048*
C190.2310 (3)0.0793 (3)0.1754 (2)0.0519 (9)
H19A0.17640.12750.18090.062*
H19B0.28170.10670.20360.062*
C200.2749 (4)0.0657 (3)0.0859 (3)0.0641 (12)
H20A0.33480.02470.08100.077*
H20B0.29400.13140.06200.077*
C210.2044 (3)0.0170 (3)0.0393 (2)0.0670 (12)
H21A0.14980.06310.03600.080*
H21B0.23870.00320.01600.080*
C220.1630 (4)0.0807 (3)0.0790 (2)0.0602 (11)
H22A0.11210.10660.05030.072*
H22B0.21610.13050.07420.072*
C230.1184 (3)0.0660 (3)0.1681 (2)0.0485 (9)
H23A0.09660.13080.19220.058*
H23B0.06030.02230.17260.058*
C240.1207 (2)0.1309 (2)0.36852 (19)0.0373 (7)
H240.13150.12290.42490.045*
C250.1948 (2)0.2105 (2)0.3298 (2)0.0412 (7)
H25A0.18540.22340.27420.049*
H25B0.26240.18600.32780.049*
C260.1799 (3)0.3075 (3)0.3788 (2)0.0490 (8)
H26A0.19470.29550.43300.059*
H26B0.22600.35850.35240.059*
C270.0745 (3)0.3458 (3)0.3862 (2)0.0537 (9)
H27A0.06600.40600.42010.064*
H27B0.06160.36400.33240.064*
C280.0008 (3)0.2657 (3)0.4234 (2)0.0558 (10)
H28A0.06680.29030.42530.067*
H28B0.00960.25220.47910.067*
C290.0154 (2)0.1691 (3)0.3743 (2)0.0477 (8)
H29A0.03120.11830.40020.057*
H29B0.00180.18140.31980.057*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Au0.04093 (8)0.03425 (8)0.03913 (8)0.00328 (5)0.00472 (5)0.00191 (5)
S10.0431 (4)0.0385 (5)0.0546 (5)0.0042 (4)0.0096 (4)0.0074 (4)
P10.0378 (4)0.0335 (4)0.0355 (4)0.0002 (3)0.0028 (3)0.0008 (3)
O10.0592 (15)0.0424 (14)0.0606 (16)0.0018 (12)0.0163 (12)0.0119 (12)
N10.0439 (17)0.0524 (18)0.064 (2)0.0025 (15)0.0108 (15)0.0019 (15)
C10.050 (2)0.039 (2)0.047 (2)0.0068 (15)0.0062 (16)0.0050 (14)
C20.0348 (17)0.051 (2)0.072 (3)0.0081 (16)0.0043 (17)0.0029 (19)
C30.043 (2)0.054 (2)0.076 (3)0.0027 (17)0.0061 (19)0.000 (2)
C40.043 (2)0.071 (3)0.079 (3)0.006 (2)0.001 (2)0.007 (2)
C50.048 (2)0.054 (3)0.113 (4)0.0004 (19)0.002 (3)0.002 (3)
C60.050 (2)0.065 (3)0.101 (4)0.002 (2)0.004 (2)0.020 (3)
C70.040 (2)0.066 (3)0.084 (3)0.0013 (19)0.0061 (19)0.016 (2)
C80.080 (3)0.115 (5)0.098 (4)0.010 (3)0.013 (3)0.025 (3)
C90.075 (3)0.046 (2)0.066 (3)0.010 (2)0.025 (2)0.0031 (18)
C100.114 (4)0.063 (3)0.079 (3)0.008 (3)0.022 (3)0.022 (3)
C110.100 (4)0.068 (3)0.079 (3)0.022 (3)0.026 (3)0.001 (2)
C120.0438 (19)0.0367 (19)0.0438 (19)0.0081 (14)0.0025 (15)0.0008 (14)
C130.054 (2)0.052 (2)0.048 (2)0.0014 (17)0.0096 (17)0.0102 (16)
C140.077 (3)0.060 (3)0.062 (3)0.011 (2)0.023 (2)0.010 (2)
C150.064 (3)0.079 (3)0.077 (3)0.023 (2)0.026 (2)0.006 (2)
C160.046 (2)0.101 (4)0.089 (4)0.017 (2)0.017 (2)0.005 (3)
C170.0386 (19)0.067 (3)0.063 (2)0.0069 (18)0.0053 (17)0.008 (2)
C180.0428 (17)0.0397 (19)0.0358 (17)0.0096 (14)0.0004 (13)0.0027 (13)
C190.060 (2)0.045 (2)0.047 (2)0.0031 (17)0.0004 (17)0.0100 (15)
C200.077 (3)0.055 (3)0.051 (2)0.015 (2)0.014 (2)0.0186 (18)
C210.096 (3)0.061 (3)0.039 (2)0.030 (2)0.001 (2)0.0029 (18)
C220.092 (3)0.052 (2)0.035 (2)0.016 (2)0.008 (2)0.0033 (16)
C230.061 (2)0.046 (2)0.0375 (19)0.0088 (17)0.0063 (16)0.0052 (14)
C240.0418 (17)0.0330 (17)0.0365 (17)0.0006 (14)0.0049 (13)0.0002 (13)
C250.0474 (18)0.0379 (19)0.0371 (17)0.0019 (15)0.0046 (14)0.0002 (13)
C260.063 (2)0.0391 (19)0.045 (2)0.0057 (17)0.0084 (17)0.0003 (15)
C270.077 (3)0.0328 (19)0.052 (2)0.0086 (18)0.0120 (19)0.0050 (15)
C280.058 (2)0.044 (2)0.063 (2)0.0100 (18)0.0037 (19)0.0075 (18)
C290.0426 (18)0.041 (2)0.058 (2)0.0021 (15)0.0032 (16)0.0055 (16)
Geometric parameters (Å, º) top
Au—P12.2692 (9)C15—C161.517 (7)
Au—S12.3051 (9)C15—H15A0.9800
S1—C11.766 (4)C15—H15B0.9800
P1—C121.837 (4)C16—C171.521 (5)
P1—C181.832 (3)C16—H16A0.9800
P1—C241.858 (3)C16—H16B0.9800
O1—C11.365 (4)C17—H17A0.9800
O1—C91.456 (5)C17—H17B0.9800
N1—C11.266 (5)C18—C191.524 (5)
N1—C21.420 (5)C18—C231.529 (5)
C2—C31.372 (6)C18—H180.9900
C2—C71.387 (6)C19—C201.527 (5)
C3—C41.421 (6)C19—H19A0.9800
C3—H30.9400C19—H19B0.9800
C4—C51.383 (6)C20—C211.498 (7)
C4—C81.480 (7)C20—H20A0.9800
C5—C61.359 (7)C20—H20B0.9800
C5—H50.9400C21—C221.529 (6)
C6—C71.379 (6)C21—H21A0.9800
C6—H60.9400C21—H21B0.9800
C7—H70.9400C22—C231.525 (5)
C8—H8A0.9700C22—H22A0.9800
C8—H8B0.9700C22—H22B0.9800
C8—H8C0.9700C23—H23A0.9800
C9—C111.509 (6)C23—H23B0.9800
C9—C101.511 (7)C24—C291.522 (4)
C9—H90.9900C24—C251.534 (4)
C10—H10A0.9700C24—H240.9900
C10—H10B0.9700C25—C261.529 (5)
C10—H10C0.9700C25—H25A0.9800
C11—H11A0.9700C25—H25B0.9800
C11—H11B0.9700C26—C271.521 (5)
C11—H11C0.9700C26—H26A0.9800
C12—C171.524 (5)C26—H26B0.9800
C12—C131.527 (5)C27—C281.528 (5)
C12—H120.9900C27—H27A0.9800
C13—C141.522 (5)C27—H27B0.9800
C13—H13A0.9800C28—C291.525 (5)
C13—H13B0.9800C28—H28A0.9800
C14—C151.511 (6)C28—H28B0.9800
C14—H14A0.9800C29—H29A0.9800
C14—H14B0.9800C29—H29B0.9800
P1—Au—S1174.73 (3)C15—C16—H16B109.4
C1—S1—Au105.20 (13)C17—C16—H16B109.4
C12—P1—C18106.37 (16)H16A—C16—H16B108.0
C12—P1—C24106.32 (16)C12—C17—C16111.4 (3)
C18—P1—C24108.42 (15)C12—C17—H17A109.4
C12—P1—Au112.19 (12)C16—C17—H17A109.4
C18—P1—Au114.12 (11)C12—C17—H17B109.4
C24—P1—Au109.07 (10)C16—C17—H17B109.4
C1—O1—C9118.3 (3)H17A—C17—H17B108.0
C1—N1—C2121.8 (3)C19—C18—C23109.9 (3)
N1—C1—O1121.0 (3)C19—C18—P1112.2 (2)
N1—C1—S1126.4 (3)C23—C18—P1110.2 (2)
O1—C1—S1112.7 (3)C19—C18—H18108.1
C3—C2—N1122.1 (4)C23—C18—H18108.1
C3—C2—C7119.0 (4)P1—C18—H18108.1
N1—C2—C7118.7 (4)C18—C19—C20111.4 (3)
C2—C3—C4121.1 (4)C18—C19—H19A109.3
C2—C3—H3119.5C20—C19—H19A109.3
C4—C3—H3119.5C18—C19—H19B109.3
C5—C4—C3117.7 (5)C20—C19—H19B109.3
C5—C4—C8122.7 (5)H19A—C19—H19B108.0
C3—C4—C8119.6 (5)C21—C20—C19112.8 (4)
C6—C5—C4121.3 (5)C21—C20—H20A109.0
C6—C5—H5119.4C19—C20—H20A109.0
C4—C5—H5119.4C21—C20—H20B109.0
C5—C6—C7120.5 (5)C19—C20—H20B109.0
C5—C6—H6119.7H20A—C20—H20B107.8
C7—C6—H6119.7C20—C21—C22111.6 (3)
C6—C7—C2120.5 (5)C20—C21—H21A109.3
C6—C7—H7119.8C22—C21—H21A109.3
C2—C7—H7119.8C20—C21—H21B109.3
C4—C8—H8A109.5C22—C21—H21B109.3
C4—C8—H8B109.5H21A—C21—H21B108.0
H8A—C8—H8B109.5C21—C22—C23111.8 (3)
C4—C8—H8C109.5C21—C22—H22A109.3
H8A—C8—H8C109.5C23—C22—H22A109.3
H8B—C8—H8C109.5C21—C22—H22B109.3
O1—C9—C11111.5 (4)C23—C22—H22B109.3
O1—C9—C10105.2 (4)H22A—C22—H22B107.9
C11—C9—C10111.4 (4)C18—C23—C22111.4 (3)
O1—C9—H9109.5C18—C23—H23A109.4
C11—C9—H9109.5C22—C23—H23A109.4
C10—C9—H9109.5C18—C23—H23B109.4
C9—C10—H10A109.5C22—C23—H23B109.4
C9—C10—H10B109.5H23A—C23—H23B108.0
H10A—C10—H10B109.5C29—C24—C25110.2 (3)
C9—C10—H10C109.5C29—C24—P1112.3 (2)
H10A—C10—H10C109.5C25—C24—P1115.1 (2)
H10B—C10—H10C109.5C29—C24—H24106.2
C9—C11—H11A109.5C25—C24—H24106.2
C9—C11—H11B109.5P1—C24—H24106.2
H11A—C11—H11B109.5C24—C25—C26110.1 (3)
C9—C11—H11C109.5C24—C25—H25A109.6
H11A—C11—H11C109.5C26—C25—H25A109.6
H11B—C11—H11C109.5C24—C25—H25B109.6
C17—C12—C13110.0 (3)C26—C25—H25B109.6
C17—C12—P1115.6 (2)H25A—C25—H25B108.1
C13—C12—P1111.5 (2)C27—C26—C25111.3 (3)
C17—C12—H12106.4C27—C26—H26A109.4
C13—C12—H12106.4C25—C26—H26A109.4
P1—C12—H12106.4C27—C26—H26B109.4
C12—C13—C14111.8 (3)C25—C26—H26B109.4
C12—C13—H13A109.3H26A—C26—H26B108.0
C14—C13—H13A109.3C28—C27—C26110.5 (3)
C12—C13—H13B109.3C28—C27—H27A109.6
C14—C13—H13B109.3C26—C27—H27A109.6
H13A—C13—H13B107.9C28—C27—H27B109.6
C15—C14—C13111.0 (3)C26—C27—H27B109.6
C15—C14—H14A109.4H27A—C27—H27B108.1
C13—C14—H14A109.4C27—C28—C29110.9 (3)
C15—C14—H14B109.4C27—C28—H28A109.5
C13—C14—H14B109.4C29—C28—H28A109.5
H14A—C14—H14B108.0C27—C28—H28B109.5
C14—C15—C16111.3 (4)C29—C28—H28B109.5
C14—C15—H15A109.4H28A—C28—H28B108.0
C16—C15—H15A109.4C24—C29—C28110.5 (3)
C14—C15—H15B109.4C24—C29—H29A109.6
C16—C15—H15B109.4C28—C29—H29A109.6
H15A—C15—H15B108.0C24—C29—H29B109.6
C15—C16—C17111.3 (4)C28—C29—H29B109.6
C15—C16—H16A109.4H29A—C29—H29B108.1
C17—C16—H16A109.4
P1—Au—S1—C1107.5 (3)C13—C14—C15—C1655.5 (5)
S1—Au—P1—C1274.2 (3)C14—C15—C16—C1755.8 (5)
S1—Au—P1—C18164.8 (3)C13—C12—C17—C1655.6 (4)
S1—Au—P1—C2443.3 (3)P1—C12—C17—C16177.1 (3)
C2—N1—C1—O1178.5 (3)C15—C16—C17—C1256.1 (5)
C2—N1—C1—S12.8 (6)C12—P1—C18—C1953.4 (3)
C9—O1—C1—N14.5 (5)C24—P1—C18—C19167.4 (3)
C9—O1—C1—S1174.3 (3)Au—P1—C18—C1970.8 (3)
Au—S1—C1—N1171.7 (3)C12—P1—C18—C23176.2 (2)
Au—S1—C1—O17.1 (3)C24—P1—C18—C2369.8 (3)
C1—N1—C2—C358.2 (5)Au—P1—C18—C2352.0 (2)
C1—N1—C2—C7127.9 (4)C23—C18—C19—C2055.8 (4)
N1—C2—C3—C4175.5 (3)P1—C18—C19—C20178.8 (3)
C7—C2—C3—C41.6 (5)C18—C19—C20—C2154.8 (5)
C2—C3—C4—C50.6 (6)C19—C20—C21—C2252.5 (4)
C2—C3—C4—C8179.7 (4)C20—C21—C22—C2352.9 (5)
C3—C4—C5—C60.1 (6)C19—C18—C23—C2256.7 (4)
C8—C4—C5—C6179.5 (4)P1—C18—C23—C22179.2 (2)
C4—C5—C6—C70.1 (7)C21—C22—C23—C1855.4 (5)
C5—C6—C7—C21.1 (6)C12—P1—C24—C29147.5 (2)
C3—C2—C7—C61.8 (6)C18—P1—C24—C2998.5 (3)
N1—C2—C7—C6175.9 (3)Au—P1—C24—C2926.4 (3)
C1—O1—C9—C1182.5 (5)C12—P1—C24—C2585.2 (3)
C1—O1—C9—C10156.6 (4)C18—P1—C24—C2528.8 (3)
C18—P1—C12—C1762.6 (3)Au—P1—C24—C25153.6 (2)
C24—P1—C12—C1752.8 (3)C29—C24—C25—C2657.6 (4)
Au—P1—C12—C17172.0 (2)P1—C24—C25—C26174.1 (2)
C18—P1—C12—C13170.8 (2)C24—C25—C26—C2757.0 (4)
C24—P1—C12—C1373.8 (3)C25—C26—C27—C2856.3 (4)
Au—P1—C12—C1345.4 (3)C26—C27—C28—C2956.4 (4)
C17—C12—C13—C1455.7 (4)C25—C24—C29—C2858.0 (4)
P1—C12—C13—C14174.7 (3)P1—C24—C29—C28172.1 (3)
C12—C13—C14—C1555.9 (5)C27—C28—C29—C2457.5 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C16—H16a···Cgi0.982.983.655 (5)127
Symmetry code: (i) x1, y, z.

Experimental details

Crystal data
Chemical formula[Au(C11H14NOS)(C18H33P)]
Mr685.67
Crystal system, space groupMonoclinic, P21/c
Temperature (K)223
a, b, c (Å)13.7415 (18), 13.3528 (18), 16.788 (2)
β (°) 100.308 (3)
V3)3030.7 (7)
Z4
Radiation typeMo Kα
µ (mm1)5.00
Crystal size (mm)0.37 × 0.10 × 0.10
Data collection
DiffractometerBruker SMART CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2000)
Tmin, Tmax0.445, 1.000
No. of measured, independent and
observed [I > 2σ(I)] reflections
20885, 6943, 5710
Rint0.031
(sin θ/λ)max1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.028, 0.072, 1.03
No. of reflections6943
No. of parameters308
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)1.60, 0.40

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), PATTY in DIRDIF92 (Beurskens et al., 1992), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006), publCIF (Westrip, 2010).

Selected geometric parameters (Å, º) top
Au—P12.2692 (9)Au—S12.3051 (9)
P1—Au—S1174.73 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C16—H16a···Cgi0.982.983.655 (5)127
Symmetry code: (i) x1, y, z.
 

Acknowledgements

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

References

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First citationBrandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany.  Google Scholar
First citationBruker (2000). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
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First citationHo, S. Y. & Tiekink, E. R. T. (2007). CrystEngComm, 9, 368–378.  Web of Science CSD CrossRef CAS Google Scholar
First citationKuan, F. S., Ho, S. Y., Tadbuppa, P. P. & Tiekink, E. R. T. (2008). CrystEngComm, 10, 548–564.  Web of Science CSD CrossRef CAS Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationWestrip, S. P. (2010). publCIF. In preparation.  Google Scholar

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