[(Z)-O-Ethyl-N-(o-tol­yl)thio­carbamato-κS](triphenyl­phosphine-κP)gold(I)

Tadbuppa, P.P.; Tiekink, E.R.T.

doi:10.1107/S1600536809048466

metal-organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 65| Part 12| December 2009| Page m1612

doi:10.1107/S1600536809048466

Open

access

[(Z)-O-Ethyl-N-(o-tolyl)thiocarbamato-κS](triphenylphosphine-κP)gold(I)

Primjira P. Tadbuppa ^a and Edward R. T. Tiekink ^b ^*

^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 13 November 2009; accepted 15 November 2009; online 21 November 2009)

The title compound, [Au(C₁₀H₁₂NOS)(C₁₈H₁₅P)], features a linear geometry for the Au atom defined by the S and P donor atoms. A small deviation from the ideal geometry is noted and is ascribed to an intramolecular Au⋯O contact [2.936 (4) Å]. Inversion dimers are formed in the crystal structure mediated by C—H⋯π interactions between centrosymmetrically related o-tolyl residues [C⋯Cg = 3.532 (6) Å].

Related literature

For 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

Crystal data

[Au(C₁₀H₁₂NOS)(C₁₈H₁₅P)]
M_r = 653.50
Triclinic, $[P \overline 1]$
a = 9.3378 (6) Å
b = 10.1665 (6) Å
c = 13.9711 (8) Å
α = 95.514 (1)°
β = 103.371 (1)°
γ = 98.334 (1)°
V = 1265.11 (13) Å³
Z = 2
Mo Kα radiation
μ = 5.98 mm⁻¹
T = 223 K
0.24 × 0.13 × 0.03 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2000 ) T_min = 0.311, T_max = 1
8823 measured reflections
5772 independent reflections
5279 reflections with I > 2σ(I)
R_int = 0.023

Refinement

R[F² > 2σ(F²)] = 0.031
wR(F²) = 0.104
S = 1.07
5772 reflections
299 parameters
H-atom parameters constrained
Δρ_max = 1.62 e Å⁻³
Δρ_min = −1.26 e Å⁻³

Table 1
Selected geometric parameters (Å, °)

Au—S1	2.3105 (11)
Au—P1	2.2509 (11)

P1—Au—S1	177.00 (4)

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: PATTY in DIRDIF92 (Beurskens et al., 1992 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: DIAMOND (Brandenburg, 2006 ); software used to prepare material for publication: publCIF (Westrip, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809048466/sj2686sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809048466/sj2686Isup2.hkl

checkCIF report

Comment top

The title compound, Ph₃Au[SC(OEt)N(o-tolyl), (I), was synthesized during the course of systematic studies of phosphinegold(I) thiocarbamides (Ho et al. 2006; Ho & Tiekink, 2007; Kuan et al., 2008)..

The gold atom in (I) exists in a linear geometry defined by an S,P donor set, Table 1 and Fig. 1. The small deviation from linearity is due to the close approach of the O1 atom to Au [Au···O = 2.936 (4) Å]. The anion, having C1—S1 = 1.768 (5) Å and C1N1 = 1.254 (6) Å, coordinates as a thiolate ligand. The configuration about the C1N1 double bond is Z.

In the crystal structure of (I), supramolecular dimers are formed between centrosymmetric pairs of o-tolyl residues owing to the presence of C—H···π interactions whereby the π system is defined by the (C2–C7) ring; C8–H8c···Cgⁱ = 2.67 Å, C8···Cgⁱ = 3.532 (6) Å with an angle at H8c = 148 ° for i: -1 - x, 1 - y, -z.

Related literature top

For 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 Ph₃AuCl and EtOC(S)N(H)(o-tolyl) in the presence of base (Hall et al., 1993).

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: DIAMOND (Brandenburg, 2006); software used to prepare material for publication: publCIF (Westrip, 2009\bbr09).

Figures top

	Fig. 1. Molecular structure of (I) showing atom-labelling scheme and displacement ellipsoids at the 50% probability level.
	Fig. 2. The supramolecular dimer in (I) mediated by C—H···π contacts (purple dashed lines). Colour code: Au, orange; S, yellow; P, pink; O, red; N, blue; C, grey; and H, green.

[(Z)-O-Ethyl-N-(o-tolyl)thiocarbamato- κS](triphenylphosphine-κP)gold(I) top

Crystal data top

[Au(C₁₀H₁₂NOS)(C₁₈H₁₅P)]	Z = 2
M_r = 653.50	F(000) = 640
Triclinic, P1	D_x = 1.716 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71069 Å
a = 9.3378 (6) Å	Cell parameters from 5740 reflections
b = 10.1665 (6) Å	θ = 2.3–29.9°
c = 13.9711 (8) Å	µ = 5.98 mm⁻¹
α = 95.514 (1)°	T = 223 K
β = 103.371 (1)°	Block, colourless
γ = 98.334 (1)°	0.24 × 0.13 × 0.03 mm
V = 1265.11 (13) Å³

Data collection top

Bruker SMART CCD diffractometer	5772 independent reflections
Radiation source: fine-focus sealed tube	5279 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.023
ω scans	θ_max = 27.5°, θ_min = 1.5°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −12→11
T_min = 0.311, T_max = 1	k = −10→13
8823 measured reflections	l = −17→18

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.031	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.104	H-atom parameters constrained
S = 1.07	w = 1/[σ²(F_o²) + (0.0692P)²] where P = (F_o² + 2F_c²)/3
5772 reflections	(Δ/σ)_max = 0.001
299 parameters	Δρ_max = 1.62 e Å⁻³
0 restraints	Δρ_min = −1.26 e Å⁻³

Crystal data top

[Au(C₁₀H₁₂NOS)(C₁₈H₁₅P)]	γ = 98.334 (1)°
M_r = 653.50	V = 1265.11 (13) Å³
Triclinic, P1	Z = 2
a = 9.3378 (6) Å	Mo Kα radiation
b = 10.1665 (6) Å	µ = 5.98 mm⁻¹
c = 13.9711 (8) Å	T = 223 K
α = 95.514 (1)°	0.24 × 0.13 × 0.03 mm
β = 103.371 (1)°

Data collection top

Bruker SMART CCD diffractometer	5772 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2000)	5279 reflections with I > 2σ(I)
T_min = 0.311, T_max = 1	R_int = 0.023
8823 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.031	0 restraints
wR(F²) = 0.104	H-atom parameters constrained
S = 1.07	Δρ_max = 1.62 e Å⁻³
5772 reflections	Δρ_min = −1.26 e Å⁻³
299 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

	x	y	z	U_iso*/U_eq
Au	0.147930 (18)	0.358507 (16)	0.308910 (12)	0.03424 (8)
S1	−0.00461 (14)	0.49405 (12)	0.22765 (9)	0.0352 (2)
P1	0.28887 (13)	0.21714 (12)	0.38273 (9)	0.0305 (2)
O1	−0.1318 (4)	0.2462 (3)	0.1600 (3)	0.0419 (8)
N1	−0.2434 (5)	0.3967 (4)	0.0724 (3)	0.0392 (9)
C1	−0.1424 (5)	0.3740 (5)	0.1420 (3)	0.0340 (9)
C2	−0.2509 (5)	0.5300 (5)	0.0506 (4)	0.0368 (10)
C3	−0.3452 (5)	0.6059 (5)	0.0885 (3)	0.0375 (10)
C4	−0.3575 (6)	0.7297 (5)	0.0590 (4)	0.0435 (11)
H4	−0.4198	0.7813	0.0840	0.052*
C5	−0.2799 (6)	0.7804 (6)	−0.0070 (4)	0.0483 (13)
H5	−0.2893	0.8658	−0.0256	0.058*
C6	−0.1902 (6)	0.7060 (6)	−0.0448 (4)	0.0447 (12)
H6	−0.1390	0.7395	−0.0903	0.054*
C7	−0.1747 (5)	0.5813 (6)	−0.0160 (4)	0.0412 (11)
H7	−0.1120	0.5307	−0.0417	0.049*
C8	−0.4332 (6)	0.5472 (6)	0.1575 (4)	0.0461 (12)
H8A	−0.4931	0.6107	0.1765	0.069*
H8B	−0.3648	0.5289	0.2164	0.069*
H8C	−0.4981	0.4645	0.1238	0.069*
C9	−0.2431 (6)	0.1389 (5)	0.0974 (4)	0.0476 (12)
H9A	−0.1996	0.0572	0.0923	0.057*
H9B	−0.2735	0.1637	0.0305	0.057*
C10	−0.3760 (7)	0.1122 (7)	0.1382 (5)	0.0568 (15)
H10A	−0.4484	0.0400	0.0952	0.085*
H10B	−0.4203	0.1925	0.1420	0.085*
H10C	−0.3462	0.0866	0.2040	0.085*
C11	0.4873 (5)	0.2811 (5)	0.4272 (4)	0.0336 (9)
C12	0.5675 (6)	0.2763 (5)	0.5233 (4)	0.0425 (11)
H12	0.5166	0.2442	0.5694	0.051*
C13	0.7199 (6)	0.3175 (6)	0.5527 (4)	0.0490 (13)
H13	0.7724	0.3139	0.6182	0.059*
C14	0.7945 (6)	0.3639 (6)	0.4854 (5)	0.0523 (14)
H14	0.8989	0.3902	0.5047	0.063*
C15	0.7178 (6)	0.3723 (6)	0.3895 (5)	0.0509 (13)
H15	0.7697	0.4056	0.3443	0.061*
C16	0.5622 (6)	0.3310 (5)	0.3600 (4)	0.0449 (11)
H16	0.5092	0.3372	0.2951	0.054*
C17	0.2775 (5)	0.0655 (4)	0.2989 (3)	0.0317 (9)
C18	0.3943 (6)	−0.0073 (5)	0.3093 (4)	0.0413 (11)
H18	0.4832	0.0241	0.3587	0.050*
C19	0.3800 (7)	−0.1259 (6)	0.2472 (4)	0.0479 (13)
H19	0.4599	−0.1736	0.2534	0.058*
C20	0.2469 (8)	−0.1739 (6)	0.1757 (5)	0.0550 (14)
H20	0.2355	−0.2559	0.1351	0.066*
C21	0.1319 (7)	−0.1011 (7)	0.1645 (5)	0.0578 (15)
H21	0.0427	−0.1331	0.1155	0.069*
C22	0.1467 (6)	0.0183 (6)	0.2245 (4)	0.0436 (11)
H22	0.0685	0.0682	0.2153	0.052*
C23	0.2305 (5)	0.1605 (5)	0.4895 (3)	0.0328 (9)
C24	0.2240 (6)	0.0302 (5)	0.5088 (4)	0.0389 (10)
H24	0.2465	−0.0348	0.4647	0.047*
C25	0.1840 (6)	−0.0054 (6)	0.5941 (4)	0.0478 (12)
H25	0.1777	−0.0949	0.6068	0.057*
C26	0.1532 (6)	0.0910 (6)	0.6604 (4)	0.0467 (12)
H26	0.1288	0.0670	0.7188	0.056*
C27	0.1583 (7)	0.2195 (6)	0.6411 (4)	0.0502 (13)
H27	0.1370	0.2843	0.6860	0.060*
C28	0.1950 (6)	0.2562 (5)	0.5551 (4)	0.0425 (11)
H28	0.1959	0.3449	0.5412	0.051*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Au	0.03477 (12)	0.03251 (12)	0.03386 (12)	0.01184 (8)	0.00062 (8)	0.00697 (7)
S1	0.0354 (6)	0.0300 (5)	0.0369 (6)	0.0114 (4)	−0.0012 (5)	0.0052 (4)
P1	0.0305 (5)	0.0294 (6)	0.0300 (6)	0.0095 (4)	0.0012 (4)	0.0054 (4)
O1	0.0446 (19)	0.0308 (17)	0.0437 (19)	0.0065 (14)	−0.0023 (15)	0.0060 (14)
N1	0.038 (2)	0.037 (2)	0.041 (2)	0.0108 (17)	0.0020 (17)	0.0072 (17)
C1	0.035 (2)	0.030 (2)	0.036 (2)	0.0089 (18)	0.0053 (19)	0.0039 (18)
C2	0.028 (2)	0.040 (3)	0.036 (2)	0.0070 (19)	−0.0033 (18)	0.0013 (19)
C3	0.039 (2)	0.041 (3)	0.030 (2)	0.011 (2)	0.0010 (19)	0.0030 (19)
C4	0.044 (3)	0.044 (3)	0.040 (3)	0.012 (2)	0.005 (2)	−0.001 (2)
C5	0.052 (3)	0.038 (3)	0.047 (3)	0.003 (2)	0.000 (2)	0.008 (2)
C6	0.044 (3)	0.045 (3)	0.043 (3)	0.004 (2)	0.004 (2)	0.012 (2)
C7	0.034 (2)	0.047 (3)	0.043 (3)	0.016 (2)	0.004 (2)	0.007 (2)
C8	0.048 (3)	0.053 (3)	0.039 (3)	0.015 (2)	0.011 (2)	0.005 (2)
C9	0.053 (3)	0.031 (2)	0.050 (3)	0.007 (2)	−0.002 (2)	−0.001 (2)
C10	0.047 (3)	0.053 (3)	0.065 (4)	0.005 (3)	0.002 (3)	0.013 (3)
C11	0.030 (2)	0.029 (2)	0.038 (2)	0.0040 (17)	0.0017 (18)	0.0047 (18)
C12	0.042 (3)	0.038 (3)	0.041 (3)	0.000 (2)	0.002 (2)	0.005 (2)
C13	0.039 (3)	0.042 (3)	0.052 (3)	0.005 (2)	−0.013 (2)	0.001 (2)
C14	0.034 (3)	0.038 (3)	0.077 (4)	0.000 (2)	0.002 (3)	0.004 (3)
C15	0.046 (3)	0.040 (3)	0.068 (4)	−0.002 (2)	0.023 (3)	0.007 (3)
C16	0.047 (3)	0.041 (3)	0.047 (3)	0.010 (2)	0.010 (2)	0.010 (2)
C17	0.033 (2)	0.028 (2)	0.034 (2)	0.0051 (17)	0.0085 (18)	0.0054 (17)
C18	0.046 (3)	0.041 (3)	0.036 (2)	0.009 (2)	0.008 (2)	0.003 (2)
C19	0.063 (4)	0.039 (3)	0.049 (3)	0.016 (3)	0.023 (3)	0.007 (2)
C20	0.075 (4)	0.039 (3)	0.051 (3)	0.005 (3)	0.023 (3)	−0.006 (2)
C21	0.057 (3)	0.058 (4)	0.047 (3)	−0.002 (3)	0.002 (3)	−0.007 (3)
C22	0.036 (2)	0.049 (3)	0.037 (3)	0.001 (2)	0.000 (2)	−0.001 (2)
C23	0.032 (2)	0.036 (2)	0.031 (2)	0.0124 (18)	0.0045 (17)	0.0039 (18)
C24	0.044 (3)	0.037 (2)	0.039 (3)	0.014 (2)	0.009 (2)	0.010 (2)
C25	0.056 (3)	0.045 (3)	0.046 (3)	0.010 (2)	0.015 (2)	0.013 (2)
C26	0.044 (3)	0.058 (3)	0.041 (3)	0.010 (2)	0.014 (2)	0.010 (2)
C27	0.050 (3)	0.059 (4)	0.042 (3)	0.014 (3)	0.016 (2)	−0.007 (3)
C28	0.047 (3)	0.037 (3)	0.045 (3)	0.015 (2)	0.011 (2)	−0.001 (2)

Geometric parameters (Å, º) top

Au—S1	2.3105 (11)	C12—C13	1.375 (7)
Au—P1	2.2509 (11)	C12—H12	0.9400
S1—C1	1.768 (5)	C13—C14	1.373 (9)
P1—C11	1.812 (5)	C13—H13	0.9400
P1—C23	1.817 (5)	C14—C15	1.382 (9)
P1—C17	1.819 (5)	C14—H14	0.9400
O1—C1	1.360 (6)	C15—C16	1.403 (8)
O1—C9	1.450 (6)	C15—H15	0.9400
N1—C1	1.254 (6)	C16—H16	0.9400
N1—C2	1.425 (6)	C17—C18	1.392 (7)
C2—C7	1.391 (7)	C17—C22	1.396 (6)
C2—C3	1.410 (7)	C18—C19	1.386 (8)
C3—C4	1.374 (7)	C18—H18	0.9400
C3—C8	1.514 (7)	C19—C20	1.392 (9)
C4—C5	1.390 (8)	C19—H19	0.9400
C4—H4	0.9400	C20—C21	1.379 (9)
C5—C6	1.366 (8)	C20—H20	0.9400
C5—H5	0.9400	C21—C22	1.377 (8)
C6—C7	1.384 (7)	C21—H21	0.9400
C6—H6	0.9400	C22—H22	0.9400
C7—H7	0.9400	C23—C24	1.372 (7)
C8—H8A	0.9700	C23—C28	1.401 (7)
C8—H8B	0.9700	C24—C25	1.393 (7)
C8—H8C	0.9700	C24—H24	0.9400
C9—C10	1.482 (9)	C25—C26	1.390 (8)
C9—H9A	0.9800	C25—H25	0.9400
C9—H9B	0.9800	C26—C27	1.356 (9)
C10—H10A	0.9700	C26—H26	0.9400
C10—H10B	0.9700	C27—C28	1.392 (8)
C10—H10C	0.9700	C27—H27	0.9400
C11—C16	1.387 (7)	C28—H28	0.9400
C11—C12	1.387 (7)

P1—Au—S1	177.00 (4)	C13—C12—C11	121.4 (5)
C1—S1—Au	101.39 (16)	C13—C12—H12	119.3
C11—P1—C23	105.3 (2)	C11—C12—H12	119.3
C11—P1—C17	104.4 (2)	C14—C13—C12	119.4 (5)
C23—P1—C17	105.6 (2)	C14—C13—H13	120.3
C11—P1—Au	116.15 (15)	C12—C13—H13	120.3
C23—P1—Au	112.80 (15)	C13—C14—C15	120.7 (5)
C17—P1—Au	111.68 (15)	C13—C14—H14	119.6
C1—O1—C9	117.5 (4)	C15—C14—H14	119.6
C1—N1—C2	120.8 (4)	C14—C15—C16	119.7 (5)
N1—C1—O1	120.6 (4)	C14—C15—H15	120.1
N1—C1—S1	127.0 (4)	C16—C15—H15	120.1
O1—C1—S1	112.4 (3)	C11—C16—C15	119.5 (5)
C7—C2—C3	119.5 (5)	C11—C16—H16	120.2
C7—C2—N1	119.5 (5)	C15—C16—H16	120.2
C3—C2—N1	120.7 (5)	C18—C17—C22	119.2 (5)
C4—C3—C2	118.4 (5)	C18—C17—P1	121.5 (4)
C4—C3—C8	122.2 (5)	C22—C17—P1	119.3 (4)
C2—C3—C8	119.3 (5)	C19—C18—C17	120.4 (5)
C3—C4—C5	121.6 (5)	C19—C18—H18	119.8
C3—C4—H4	119.2	C17—C18—H18	119.8
C5—C4—H4	119.2	C18—C19—C20	119.8 (6)
C6—C5—C4	119.9 (5)	C18—C19—H19	120.1
C6—C5—H5	120.1	C20—C19—H19	120.1
C4—C5—H5	120.1	C21—C20—C19	119.9 (5)
C5—C6—C7	120.0 (5)	C21—C20—H20	120.0
C5—C6—H6	120.0	C19—C20—H20	120.0
C7—C6—H6	120.0	C22—C21—C20	120.5 (6)
C6—C7—C2	120.6 (5)	C22—C21—H21	119.7
C6—C7—H7	119.7	C20—C21—H21	119.7
C2—C7—H7	119.7	C21—C22—C17	120.2 (5)
C3—C8—H8A	109.5	C21—C22—H22	119.9
C3—C8—H8B	109.5	C17—C22—H22	119.9
H8A—C8—H8B	109.5	C24—C23—C28	119.6 (5)
C3—C8—H8C	109.5	C24—C23—P1	122.8 (4)
H8A—C8—H8C	109.5	C28—C23—P1	117.6 (4)
H8B—C8—H8C	109.5	C23—C24—C25	119.9 (5)
O1—C9—C10	111.1 (5)	C23—C24—H24	120.1
O1—C9—H9A	109.4	C25—C24—H24	120.1
C10—C9—H9A	109.4	C26—C25—C24	120.2 (5)
O1—C9—H9B	109.4	C26—C25—H25	119.9
C10—C9—H9B	109.4	C24—C25—H25	119.9
H9A—C9—H9B	108.0	C27—C26—C25	120.1 (5)
C9—C10—H10A	109.5	C27—C26—H26	119.9
C9—C10—H10B	109.5	C25—C26—H26	119.9
H10A—C10—H10B	109.5	C26—C27—C28	120.4 (5)
C9—C10—H10C	109.5	C26—C27—H27	119.8
H10A—C10—H10C	109.5	C28—C27—H27	119.8
H10B—C10—H10C	109.5	C27—C28—C23	119.8 (5)
C16—C11—C12	119.2 (5)	C27—C28—H28	120.1
C16—C11—P1	117.8 (4)	C23—C28—H28	120.1
C12—C11—P1	123.0 (4)

C2—N1—C1—O1	−177.2 (4)	C12—C11—C16—C15	1.7 (8)
C2—N1—C1—S1	4.3 (7)	P1—C11—C16—C15	−175.3 (4)
C9—O1—C1—N1	−1.4 (7)	C14—C15—C16—C11	−0.5 (8)
C9—O1—C1—S1	177.3 (4)	C11—P1—C17—C18	26.2 (4)
Au—S1—C1—N1	−171.6 (4)	C23—P1—C17—C18	−84.6 (4)
Au—S1—C1—O1	9.8 (4)	Au—P1—C17—C18	152.4 (4)
C1—N1—C2—C7	89.5 (6)	C11—P1—C17—C22	−156.2 (4)
C1—N1—C2—C3	−96.3 (6)	C23—P1—C17—C22	93.0 (4)
C7—C2—C3—C4	−0.7 (7)	Au—P1—C17—C22	−29.9 (4)
N1—C2—C3—C4	−174.9 (4)	C22—C17—C18—C19	−0.7 (7)
C7—C2—C3—C8	177.4 (5)	P1—C17—C18—C19	177.0 (4)
N1—C2—C3—C8	3.1 (7)	C17—C18—C19—C20	−1.5 (8)
C2—C3—C4—C5	0.2 (8)	C18—C19—C20—C21	2.3 (9)
C8—C3—C4—C5	−177.8 (5)	C19—C20—C21—C22	−0.9 (10)
C3—C4—C5—C6	0.7 (8)	C20—C21—C22—C17	−1.3 (9)
C4—C5—C6—C7	−1.1 (8)	C18—C17—C22—C21	2.1 (8)
C5—C6—C7—C2	0.6 (8)	P1—C17—C22—C21	−175.6 (4)
C3—C2—C7—C6	0.3 (7)	C11—P1—C23—C24	−93.8 (4)
N1—C2—C7—C6	174.6 (5)	C17—P1—C23—C24	16.3 (5)
C1—O1—C9—C10	−88.1 (6)	Au—P1—C23—C24	138.5 (4)
C23—P1—C11—C16	179.7 (4)	C11—P1—C23—C28	84.5 (4)
C17—P1—C11—C16	68.7 (4)	C17—P1—C23—C28	−165.4 (4)
Au—P1—C11—C16	−54.7 (4)	Au—P1—C23—C28	−43.2 (4)
C23—P1—C11—C12	2.8 (5)	C28—C23—C24—C25	−0.8 (8)
C17—P1—C11—C12	−108.2 (4)	P1—C23—C24—C25	177.5 (4)
Au—P1—C11—C12	128.4 (4)	C23—C24—C25—C26	−1.1 (8)
C16—C11—C12—C13	−1.3 (8)	C24—C25—C26—C27	1.7 (9)
P1—C11—C12—C13	175.5 (4)	C25—C26—C27—C28	−0.3 (9)
C11—C12—C13—C14	−0.3 (9)	C26—C27—C28—C23	−1.6 (9)
C12—C13—C14—C15	1.4 (9)	C24—C23—C28—C27	2.2 (8)
C13—C14—C15—C16	−1.0 (9)	P1—C23—C28—C27	−176.2 (4)

Experimental details

Crystal data
Chemical formula	[Au(C₁₀H₁₂NOS)(C₁₈H₁₅P)]
M_r	653.50
Crystal system, space group	Triclinic, P1
Temperature (K)	223
a, b, c (Å)	9.3378 (6), 10.1665 (6), 13.9711 (8)
α, β, γ (°)	95.514 (1), 103.371 (1), 98.334 (1)
V (Å³)	1265.11 (13)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	5.98
Crystal size (mm)	0.24 × 0.13 × 0.03

Data collection
Diffractometer	Bruker SMART CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2000)
T_min, T_max	0.311, 1
No. of measured, independent and observed [I > 2σ(I)] reflections	8823, 5772, 5279
R_int	0.023
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.031, 0.104, 1.07
No. of reflections	5772
No. of parameters	299
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.62, −1.26

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), PATTY in DIRDIF92 (Beurskens et al., 1992), SHELXL97 (Sheldrick, 2008), DIAMOND (Brandenburg, 2006), publCIF (Westrip, 2009\bbr09).

Selected geometric parameters (Å, º) top

Au—S1	2.3105 (11)	Au—P1	2.2509 (11)

P1—Au—S1	177.00 (4)

Acknowledgements

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

References

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. Google Scholar
Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Bruker (2000). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, U. S. A. Google Scholar
Hall, V. J., Siasios, G. & Tiekink, E. R. T. (1993). Aust. J. Chem. 46, 561–570. CSD CrossRef CAS Google Scholar
Ho, S. Y., Cheng, E. C.-C., Tiekink, E. R. T. & Yam, V. W.-W. (2006). Inorg. Chem. 45, 8165–8174. Web of Science CSD CrossRef PubMed CAS Google Scholar
Ho, S. Y. & Tiekink, E. R. T. (2007). CrystEngComm, 9, 368–378. Web of Science CSD CrossRef CAS Google Scholar
Kuan, 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
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Westrip, S. P. (2009). publCIF. In preparation. Google Scholar