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

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

doi:10.1107/S1600536809047618

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 12| December 2009| Page m1587

doi:10.1107/S1600536809047618

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[(Z)-O-Ethyl-N-(p-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 9 November 2009; accepted 10 November 2009; online 14 November 2009)

The title compound, [Au(C₁₀H₁₂NOS)(C₁₈H₁₅P)], features a linear S,P-donor set about the central Au atom. The thiocarbamate ligand is orientated to place the aryl ring in close proximity to Au [the closest Au⋯C distance is 3.238 (4) Å], which results in a small deviation from the ideal linear P—Au—S geometry.

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 ). For gold⋯π interactions, see: Tiekink & Zukerman-Schpector (2009 ).

Experimental

Crystal data

[Au(C₁₀H₁₂NOS)(C₁₈H₁₅P)]
M_r = 653.50
Triclinic, $[P \overline 1]$
a = 8.6676 (5) Å
b = 12.1397 (6) Å
c = 13.2378 (7) Å
α = 65.482 (1)°
β = 89.765 (1)°
γ = 80.635 (1)°
V = 1247.30 (12) Å³
Z = 2
Mo Kα radiation
μ = 6.07 mm⁻¹
T = 223 K
0.31 × 0.16 × 0.16 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2000 ) T_min = 0.311, T_max = 1
8852 measured reflections
5702 independent reflections
5380 reflections with I > 2σ(I)
R_int = 0.019

Refinement

R[F² > 2σ(F²)] = 0.025
wR(F²) = 0.074
S = 1.04
5702 reflections
299 parameters
H-atom parameters constrained
Δρ_max = 1.41 e Å⁻³
Δρ_min = −0.98 e Å⁻³

Table 1
Selected geometric parameters (Å, °)

Au—S1	2.2964 (9)
Au—P1	2.2601 (9)

P1—Au—S1	177.07 (3)

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/S1600536809047618/lh2951sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809047618/lh2951Isup2.hkl

checkCIF report

Comment top

Phosphinegold(I) thiocarbamides have proved relatively easy to crystallize making systematic structural investigations possible, such as monitoring the influence of phosphine and/or thiocarbamato ligands upon supramolecular aggregation patterns (Ho & Tiekink, 2007; Kuan et al., 2008) and luminescence (Ho et al. 2006). During these studies, the title compound, Ph₃Au[SC(OEt)N(p-tolyl)], (I), was synthesized.

The gold atom in (I) exists in the expected linear geometry defined by a S,P donor set, Table 1 and Fig. 1. While the thiocarbamato anion shows the expected features, i.e. a Z-conformation about the C1-N1 bond and thiolate character [C1–S1 is 1.759 (3) Å and C1-N1 is 1.265 (5) Å], its orientation within the molecule is unusual. Normally in these type of phosphinegold(I) compounds, the orientation of the thiocarbamato ligand has the O1 atom in close proximity to the Au atom. However, in (I), the aryl ring is orientated towards Au [closest Au···C2 distance = 3.238 (4) Å, and Au···Cg(C2—C7) = 3.60 Å]. The close approach of the aryl ring is responsible for the small deviation from linearity of the S,P donor set, Table 1.

Electronic and steric effects have been cited as reasons for the variation in the coordination modes of thiocarbamato ligands in their phosphinegold(I) compounds, with N-bound p-tolyl groups known to promote Au···π interactions (Kuan et al., 2008).

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). For related literature, see: Tiekink & Zukerman-Schpector (2009).

Experimental top

Compound (I) was prepared following the standard literature procedure from the reaction of Ph₃AuCl and EtOC(S)N(H)(p-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).

Figures top

Fig. 1. Molecular structure of (I) showing atom-labelling scheme and displacement ellipsoids at the 50% probability level.

[(Z)-O-Ethyl-N-(p-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 = 1.740 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71069 Å
a = 8.6676 (5) Å	Cell parameters from 6912 reflections
b = 12.1397 (6) Å	θ = 2.4–29.9°
c = 13.2378 (7) Å	µ = 6.07 mm⁻¹
α = 65.482 (1)°	T = 223 K
β = 89.765 (1)°	Block, colourless
γ = 80.635 (1)°	0.31 × 0.16 × 0.16 mm
V = 1247.30 (12) Å³

Data collection top

Bruker SMART CCD diffractometer	5702 independent reflections
Radiation source: fine-focus sealed tube	5380 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.019
ω scans	θ_max = 27.5°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −11→11
T_min = 0.311, T_max = 1	k = −14→15
8852 measured reflections	l = −11→17

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)] = 0.025	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.074	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0515P)² + 0.0366P] where P = (F_o² + 2F_c²)/3
5702 reflections	(Δ/σ)_max = 0.001
299 parameters	Δρ_max = 1.41 e Å⁻³
0 restraints	Δρ_min = −0.98 e Å⁻³

Crystal data top

[Au(C₁₀H₁₂NOS)(C₁₈H₁₅P)]	γ = 80.635 (1)°
M_r = 653.50	V = 1247.30 (12) Å³
Triclinic, P1	Z = 2
a = 8.6676 (5) Å	Mo Kα radiation
b = 12.1397 (6) Å	µ = 6.07 mm⁻¹
c = 13.2378 (7) Å	T = 223 K
α = 65.482 (1)°	0.31 × 0.16 × 0.16 mm
β = 89.765 (1)°

Data collection top

Bruker SMART CCD diffractometer	5702 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2000)	5380 reflections with I > 2σ(I)
T_min = 0.311, T_max = 1	R_int = 0.019
8852 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.025	0 restraints
wR(F²) = 0.074	H-atom parameters constrained
S = 1.04	Δρ_max = 1.41 e Å⁻³
5702 reflections	Δρ_min = −0.98 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	0.133778 (13)	0.439781 (10)	0.172306 (9)	0.03279 (6)
S1	−0.03428 (11)	0.61652 (8)	0.06097 (8)	0.03801 (18)
P1	0.28847 (10)	0.26188 (8)	0.28627 (7)	0.03056 (17)
O1	−0.1531 (3)	0.8119 (2)	0.0773 (2)	0.0404 (5)
N1	0.0908 (4)	0.7459 (3)	0.1633 (3)	0.0434 (7)
C1	−0.0164 (4)	0.7286 (3)	0.1099 (3)	0.0341 (6)
C2	0.2387 (4)	0.6696 (3)	0.2015 (3)	0.0368 (7)
C3	0.3647 (5)	0.6845 (4)	0.1339 (4)	0.0471 (8)
H3	0.3482	0.7387	0.0581	0.056*
C4	0.5130 (5)	0.6205 (4)	0.1775 (4)	0.0473 (9)
H4	0.5966	0.6326	0.1308	0.057*
C5	0.5420 (4)	0.5380 (3)	0.2896 (3)	0.0405 (8)
C6	0.4168 (5)	0.5244 (3)	0.3562 (3)	0.0408 (8)
H6	0.4331	0.4705	0.4322	0.049*
C7	0.2677 (4)	0.5889 (3)	0.3127 (3)	0.0400 (8)
H7	0.1844	0.5777	0.3596	0.048*
C8	0.7037 (5)	0.4652 (4)	0.3367 (4)	0.0589 (11)
H8A	0.7252	0.4645	0.4089	0.088*
H8B	0.7810	0.5029	0.2867	0.088*
H8C	0.7089	0.3815	0.3449	0.088*
C9	−0.1632 (4)	0.9157 (3)	0.1064 (3)	0.0400 (7)
H9A	−0.0921	0.9706	0.0639	0.048*
H9B	−0.1352	0.8872	0.1859	0.048*
C10	−0.3300 (5)	0.9812 (4)	0.0780 (4)	0.0523 (10)
H10A	−0.3432	1.0516	0.0964	0.078*
H10B	−0.3988	0.9256	0.1203	0.078*
H10C	−0.3558	1.0090	−0.0009	0.078*
C11	0.4880 (4)	0.2449 (3)	0.2467 (3)	0.0338 (6)
C12	0.5368 (4)	0.3463 (3)	0.1625 (3)	0.0399 (7)
H12	0.4657	0.4204	0.1259	0.048*
C13	0.6905 (5)	0.3367 (4)	0.1334 (4)	0.0540 (10)
H13	0.7241	0.4050	0.0778	0.065*
C14	0.7948 (5)	0.2275 (5)	0.1856 (4)	0.0569 (11)
H14	0.8991	0.2221	0.1658	0.068*
C15	0.7465 (5)	0.1256 (4)	0.2670 (4)	0.0559 (11)
H15	0.8175	0.0512	0.3019	0.067*
C16	0.5923 (5)	0.1342 (4)	0.2969 (3)	0.0439 (8)
H16	0.5587	0.0651	0.3512	0.053*
C17	0.2276 (4)	0.1190 (3)	0.3033 (3)	0.0321 (6)
C18	0.1892 (4)	0.0357 (3)	0.4049 (3)	0.0383 (7)
H18	0.1924	0.0535	0.4675	0.046*
C19	0.1460 (5)	−0.0739 (3)	0.4155 (4)	0.0444 (8)
H19	0.1196	−0.1299	0.4846	0.053*
C20	0.1424 (4)	−0.0992 (3)	0.3228 (4)	0.0456 (8)
H20	0.1145	−0.1733	0.3291	0.055*
C21	0.1794 (5)	−0.0163 (4)	0.2211 (4)	0.0453 (8)
H21	0.1759	−0.0344	0.1587	0.054*
C22	0.2216 (4)	0.0927 (3)	0.2101 (3)	0.0400 (8)
H22	0.2461	0.1490	0.1404	0.048*
C23	0.2960 (4)	0.2546 (3)	0.4263 (3)	0.0329 (6)
C24	0.1596 (4)	0.3020 (3)	0.4609 (3)	0.0400 (7)
H24	0.0671	0.3331	0.4138	0.048*
C25	0.1605 (5)	0.3033 (4)	0.5653 (3)	0.0483 (9)
H25	0.0678	0.3341	0.5892	0.058*
C26	0.2956 (5)	0.2601 (4)	0.6341 (3)	0.0496 (9)
H26	0.2960	0.2643	0.7034	0.059*
C27	0.4302 (6)	0.2107 (4)	0.6016 (3)	0.0505 (9)
H27	0.5214	0.1779	0.6500	0.061*
C28	0.4315 (4)	0.2093 (3)	0.4973 (3)	0.0421 (8)
H28	0.5245	0.1774	0.4745	0.051*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Au	0.03425 (8)	0.02878 (8)	0.03499 (9)	−0.00471 (5)	0.00208 (5)	−0.01337 (6)
S1	0.0414 (4)	0.0333 (4)	0.0401 (4)	−0.0021 (3)	−0.0074 (3)	−0.0178 (4)
P1	0.0324 (4)	0.0270 (4)	0.0332 (4)	−0.0056 (3)	0.0028 (3)	−0.0134 (3)
O1	0.0382 (12)	0.0349 (12)	0.0474 (14)	0.0010 (10)	−0.0073 (10)	−0.0193 (11)
N1	0.0396 (16)	0.0362 (15)	0.0541 (19)	0.0010 (13)	−0.0107 (14)	−0.0214 (14)
C1	0.0376 (16)	0.0299 (15)	0.0355 (16)	−0.0050 (13)	0.0019 (13)	−0.0147 (13)
C2	0.0347 (16)	0.0320 (16)	0.0493 (19)	−0.0045 (13)	−0.0058 (14)	−0.0229 (15)
C3	0.048 (2)	0.0419 (19)	0.048 (2)	−0.0037 (16)	−0.0011 (17)	−0.0176 (17)
C4	0.042 (2)	0.048 (2)	0.053 (2)	−0.0086 (17)	0.0077 (17)	−0.0216 (18)
C5	0.0341 (16)	0.0389 (18)	0.056 (2)	−0.0046 (14)	−0.0038 (15)	−0.0279 (17)
C6	0.0454 (19)	0.0317 (16)	0.0439 (19)	−0.0042 (15)	−0.0082 (15)	−0.0153 (15)
C7	0.0358 (17)	0.0353 (17)	0.051 (2)	−0.0082 (14)	0.0031 (15)	−0.0194 (16)
C8	0.041 (2)	0.058 (3)	0.080 (3)	0.0024 (19)	−0.013 (2)	−0.034 (2)
C9	0.0420 (18)	0.0328 (16)	0.0432 (19)	0.0000 (14)	0.0002 (14)	−0.0162 (15)
C10	0.047 (2)	0.046 (2)	0.056 (2)	0.0086 (17)	−0.0033 (18)	−0.0202 (19)
C11	0.0319 (15)	0.0360 (16)	0.0370 (16)	−0.0052 (13)	0.0041 (12)	−0.0190 (14)
C12	0.0380 (17)	0.0413 (18)	0.0412 (18)	−0.0096 (14)	0.0066 (14)	−0.0173 (15)
C13	0.046 (2)	0.065 (3)	0.059 (3)	−0.0207 (19)	0.0164 (19)	−0.029 (2)
C14	0.039 (2)	0.082 (3)	0.059 (3)	−0.010 (2)	0.0087 (19)	−0.039 (3)
C15	0.046 (2)	0.066 (3)	0.053 (2)	0.009 (2)	0.0006 (18)	−0.028 (2)
C16	0.045 (2)	0.0393 (19)	0.045 (2)	−0.0010 (15)	0.0049 (16)	−0.0185 (16)
C17	0.0294 (14)	0.0291 (15)	0.0396 (17)	−0.0053 (12)	−0.0002 (12)	−0.0161 (13)
C18	0.0412 (17)	0.0340 (17)	0.0427 (18)	−0.0081 (14)	0.0037 (14)	−0.0186 (15)
C19	0.045 (2)	0.0335 (17)	0.051 (2)	−0.0118 (15)	0.0093 (16)	−0.0134 (16)
C20	0.0419 (19)	0.0358 (18)	0.067 (2)	−0.0097 (15)	0.0022 (17)	−0.0280 (18)
C21	0.047 (2)	0.047 (2)	0.053 (2)	−0.0094 (16)	−0.0005 (16)	−0.0313 (18)
C22	0.0443 (19)	0.0389 (18)	0.0398 (18)	−0.0078 (15)	−0.0010 (15)	−0.0191 (15)
C23	0.0380 (16)	0.0286 (15)	0.0352 (16)	−0.0098 (12)	0.0043 (13)	−0.0149 (13)
C24	0.0390 (17)	0.0413 (18)	0.0453 (19)	−0.0116 (14)	0.0076 (14)	−0.0222 (16)
C25	0.054 (2)	0.052 (2)	0.049 (2)	−0.0184 (18)	0.0194 (18)	−0.0282 (19)
C26	0.071 (3)	0.050 (2)	0.0357 (18)	−0.026 (2)	0.0125 (18)	−0.0202 (17)
C27	0.065 (3)	0.041 (2)	0.0396 (19)	−0.0112 (18)	−0.0068 (17)	−0.0106 (16)
C28	0.0433 (19)	0.0403 (18)	0.0423 (19)	−0.0064 (15)	0.0006 (15)	−0.0171 (15)

Geometric parameters (Å, º) top

Au—S1	2.2964 (9)	C12—C13	1.385 (5)
Au—P1	2.2601 (9)	C12—H12	0.9400
S1—C1	1.759 (3)	C13—C14	1.381 (7)
P1—C11	1.810 (3)	C13—H13	0.9400
P1—C17	1.819 (3)	C14—C15	1.387 (7)
P1—C23	1.820 (3)	C14—H14	0.9400
O1—C1	1.365 (4)	C15—C16	1.392 (6)
O1—C9	1.453 (4)	C15—H15	0.9400
N1—C1	1.265 (5)	C16—H16	0.9400
N1—C2	1.409 (4)	C17—C18	1.386 (5)
C2—C7	1.385 (5)	C17—C22	1.400 (5)
C2—C3	1.395 (5)	C18—C19	1.392 (5)
C3—C4	1.378 (6)	C18—H18	0.9400
C3—H3	0.9400	C19—C20	1.386 (6)
C4—C5	1.400 (6)	C19—H19	0.9400
C4—H4	0.9400	C20—C21	1.380 (6)
C5—C6	1.383 (6)	C20—H20	0.9400
C5—C8	1.510 (5)	C21—C22	1.380 (5)
C6—C7	1.385 (5)	C21—H21	0.9400
C6—H6	0.9400	C22—H22	0.9400
C7—H7	0.9400	C23—C24	1.390 (5)
C8—H8A	0.9700	C23—C28	1.391 (5)
C8—H8B	0.9700	C24—C25	1.389 (5)
C8—H8C	0.9700	C24—H24	0.9400
C9—C10	1.498 (5)	C25—C26	1.374 (6)
C9—H9A	0.9800	C25—H25	0.9400
C9—H9B	0.9800	C26—C27	1.374 (6)
C10—H10A	0.9700	C26—H26	0.9400
C10—H10B	0.9700	C27—C28	1.388 (6)
C10—H10C	0.9700	C27—H27	0.9400
C11—C16	1.390 (5)	C28—H28	0.9400
C11—C12	1.401 (5)

P1—Au—S1	177.07 (3)	C13—C12—C11	119.6 (4)
C1—S1—Au	107.44 (12)	C13—C12—H12	120.2
C11—P1—C17	103.77 (15)	C11—C12—H12	120.2
C11—P1—C23	107.57 (15)	C14—C13—C12	120.4 (4)
C17—P1—C23	104.35 (15)	C14—C13—H13	119.8
C11—P1—Au	114.08 (12)	C12—C13—H13	119.8
C17—P1—Au	117.45 (11)	C13—C14—C15	120.4 (4)
C23—P1—Au	108.81 (11)	C13—C14—H14	119.8
C1—O1—C9	116.6 (3)	C15—C14—H14	119.8
C1—N1—C2	125.5 (3)	C14—C15—C16	119.7 (4)
N1—C1—O1	118.6 (3)	C14—C15—H15	120.2
N1—C1—S1	134.4 (3)	C16—C15—H15	120.2
O1—C1—S1	107.0 (2)	C11—C16—C15	120.1 (4)
C7—C2—C3	118.0 (3)	C11—C16—H16	119.9
C7—C2—N1	119.7 (3)	C15—C16—H16	119.9
C3—C2—N1	121.7 (3)	C18—C17—C22	119.4 (3)
C4—C3—C2	120.6 (4)	C18—C17—P1	122.3 (3)
C4—C3—H3	119.7	C22—C17—P1	118.3 (3)
C2—C3—H3	119.7	C17—C18—C19	120.9 (3)
C3—C4—C5	121.4 (4)	C17—C18—H18	119.6
C3—C4—H4	119.3	C19—C18—H18	119.6
C5—C4—H4	119.3	C20—C19—C18	119.0 (4)
C6—C5—C4	117.6 (3)	C20—C19—H19	120.5
C6—C5—C8	120.9 (4)	C18—C19—H19	120.5
C4—C5—C8	121.5 (4)	C21—C20—C19	120.5 (3)
C5—C6—C7	121.0 (4)	C21—C20—H20	119.8
C5—C6—H6	119.5	C19—C20—H20	119.8
C7—C6—H6	119.5	C20—C21—C22	120.7 (4)
C2—C7—C6	121.4 (4)	C20—C21—H21	119.6
C2—C7—H7	119.3	C22—C21—H21	119.6
C6—C7—H7	119.3	C21—C22—C17	119.5 (4)
C5—C8—H8A	109.5	C21—C22—H22	120.2
C5—C8—H8B	109.5	C17—C22—H22	120.2
H8A—C8—H8B	109.5	C24—C23—C28	119.1 (3)
C5—C8—H8C	109.5	C24—C23—P1	117.3 (3)
H8A—C8—H8C	109.5	C28—C23—P1	123.5 (3)
H8B—C8—H8C	109.5	C25—C24—C23	119.7 (4)
O1—C9—C10	106.2 (3)	C25—C24—H24	120.2
O1—C9—H9A	110.5	C23—C24—H24	120.2
C10—C9—H9A	110.5	C26—C25—C24	120.7 (4)
O1—C9—H9B	110.5	C26—C25—H25	119.7
C10—C9—H9B	110.5	C24—C25—H25	119.7
H9A—C9—H9B	108.7	C27—C26—C25	120.0 (4)
C9—C10—H10A	109.5	C27—C26—H26	120.0
C9—C10—H10B	109.5	C25—C26—H26	120.0
H10A—C10—H10B	109.5	C26—C27—C28	120.0 (4)
C9—C10—H10C	109.5	C26—C27—H27	120.0
H10A—C10—H10C	109.5	C28—C27—H27	120.0
H10B—C10—H10C	109.5	C27—C28—C23	120.4 (4)
C16—C11—C12	119.7 (3)	C27—C28—H28	119.8
C16—C11—P1	121.7 (3)	C23—C28—H28	119.8
C12—C11—P1	118.6 (3)

C2—N1—C1—O1	−179.2 (3)	P1—C11—C16—C15	−177.8 (3)
C2—N1—C1—S1	−0.6 (7)	C14—C15—C16—C11	−1.1 (6)
C9—O1—C1—N1	0.6 (5)	C11—P1—C17—C18	116.3 (3)
C9—O1—C1—S1	−178.4 (2)	C23—P1—C17—C18	3.7 (3)
Au—S1—C1—N1	25.4 (4)	Au—P1—C17—C18	−116.8 (3)
Au—S1—C1—O1	−155.85 (19)	C11—P1—C17—C22	−62.9 (3)
C1—N1—C2—C7	−102.7 (5)	C23—P1—C17—C22	−175.5 (3)
C1—N1—C2—C3	86.4 (5)	Au—P1—C17—C22	64.0 (3)
C7—C2—C3—C4	−0.1 (6)	C22—C17—C18—C19	0.5 (5)
N1—C2—C3—C4	171.0 (4)	P1—C17—C18—C19	−178.8 (3)
C2—C3—C4—C5	0.8 (6)	C17—C18—C19—C20	0.3 (6)
C3—C4—C5—C6	−1.2 (6)	C18—C19—C20—C21	−0.7 (6)
C3—C4—C5—C8	178.3 (4)	C19—C20—C21—C22	0.4 (6)
C4—C5—C6—C7	1.0 (6)	C20—C21—C22—C17	0.4 (6)
C8—C5—C6—C7	−178.5 (4)	C18—C17—C22—C21	−0.8 (5)
C3—C2—C7—C6	−0.1 (5)	P1—C17—C22—C21	178.5 (3)
N1—C2—C7—C6	−171.4 (4)	C11—P1—C23—C24	160.8 (3)
C5—C6—C7—C2	−0.4 (6)	C17—P1—C23—C24	−89.4 (3)
C1—O1—C9—C10	−171.3 (3)	Au—P1—C23—C24	36.7 (3)
C17—P1—C11—C16	−41.1 (3)	C11—P1—C23—C28	−16.4 (3)
C23—P1—C11—C16	69.1 (3)	C17—P1—C23—C28	93.4 (3)
Au—P1—C11—C16	−170.1 (3)	Au—P1—C23—C28	−140.5 (3)
C17—P1—C11—C12	138.3 (3)	C28—C23—C24—C25	−0.1 (5)
C23—P1—C11—C12	−111.5 (3)	P1—C23—C24—C25	−177.4 (3)
Au—P1—C11—C12	9.3 (3)	C23—C24—C25—C26	1.1 (6)
C16—C11—C12—C13	−2.7 (5)	C24—C25—C26—C27	−2.4 (6)
P1—C11—C12—C13	177.8 (3)	C25—C26—C27—C28	2.7 (6)
C11—C12—C13—C14	1.0 (6)	C26—C27—C28—C23	−1.7 (6)
C12—C13—C14—C15	0.6 (7)	C24—C23—C28—C27	0.4 (5)
C13—C14—C15—C16	−0.6 (7)	P1—C23—C28—C27	177.6 (3)
C12—C11—C16—C15	2.7 (6)

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)	8.6676 (5), 12.1397 (6), 13.2378 (7)
α, β, γ (°)	65.482 (1), 89.765 (1), 80.635 (1)
V (Å³)	1247.30 (12)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	6.07
Crystal size (mm)	0.31 × 0.16 × 0.16

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	8852, 5702, 5380
R_int	0.019
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.025, 0.074, 1.04
No. of reflections	5702
No. of parameters	299
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.41, −0.98

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

Selected geometric parameters (Å, º) top

Au—S1	2.2964 (9)	Au—P1	2.2601 (9)

P1—Au—S1	177.07 (3)

Acknowledgements

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

References

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