[O-Ethyl (Z)-N-(2-chloro­phen­yl)thio­carbamato-κS](tricyclo­hexyl­phosphine-κP)gold(I)

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

doi:10.1107/S160053681001189X

metal-organic compounds

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ISSN: 2056-9890

Volume 66| Part 5| May 2010| Page m498

https://doi.org/10.1107/S160053681001189X

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[O-Ethyl (Z)-N-(2-chlorophenyl)thiocarbamato-κS](tricyclohexylphosphine-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 17 March 2010; accepted 30 March 2010; online 10 April 2010)

The title compound, [Au(C₉H₉ClNOS)(C₁₈H₃₃P)], features a slightly distorted linear coordination geometry for the Au atom defined by a S,P-donor set [S—Au—P = 177.62 (5)°]. The distortion is ascribed to the close approach of the O atom, which forms an intramolecular contact of 2.970 (5) Å. Disorder was found in the structure with two positions of equal weight being resolved for the C atoms comprising the ethoxy group.

Related literature

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

Crystal data

[Au(C₉H₉ClNOS)(C₁₈H₃₃P)]
M_r = 692.06
Monoclinic, P 2₁ /n
a = 12.0513 (11) Å
b = 18.2460 (16) Å
c = 13.9712 (12) Å
β = 108.892 (2)°
V = 2906.6 (4) Å³
Z = 4
Mo Kα radiation
μ = 5.30 mm⁻¹
T = 223 K
0.16 × 0.13 × 0.08 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2000 ) T_min = 0.294, T_max = 1.000
20508 measured reflections
6663 independent reflections
5016 reflections with I > 2σ(I)
R_int = 0.045

Refinement

R[F² > 2σ(F²)] = 0.037
wR(F²) = 0.113
S = 1.07
6663 reflections
307 parameters
4 restraints
H-atom parameters constrained
Δρ_max = 1.09 e Å⁻³
Δρ_min = −0.76 e Å⁻³

Table 1
Selected bond lengths (Å)

Au—P1	2.2648 (13)
Au—S1	2.3060 (14)

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: ORTEP-3 (Farrugia, 1997 ) and DIAMOND (Brandenburg, 2006 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S160053681001189X/ez2205sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S160053681001189X/ez2205Isup2.hkl

checkCIF report

Comment top

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

The Au atom in (I), Fig. 1, is linearly coordinated within a SP donor set, Table 1. The thiocarbamate ligand coordinates as a thiolate as seen in the C1–S1 [1.734 (6) Å] and C1═N1 [1.261 (8) Å] distances. A small deviation from the ideal geometry is noted, Table 1, which is ascribed to the close approach of the O1 atom [2.970 (5) Å]. No specific intermolecular interactions are noted in the crystal packing.

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 EtOC(═S)N(H)(C₆H₄Cl-2) 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.

Structure description 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).

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

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

[O-Ethyl (Z)-N-(2-chlorophenyl)thiocarbamato- κS](tricyclohexylphosphine-κP)gold(I) top

Crystal data top

[Au(C₉H₉ClNOS)(C₁₈H₃₃P)]	F(000) = 1384
M_r = 692.06	D_x = 1.581 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71069 Å
Hall symbol: -P 2yn	Cell parameters from 4436 reflections
a = 12.0513 (11) Å	θ = 2.1–25.0°
b = 18.2460 (16) Å	µ = 5.30 mm⁻¹
c = 13.9712 (12) Å	T = 223 K
β = 108.892 (2)°	Block, colourless
V = 2906.6 (4) Å³	0.16 × 0.13 × 0.08 mm
Z = 4

Data collection top

Bruker SMART CCD diffractometer	6663 independent reflections
Radiation source: fine-focus sealed tube	5016 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.045
ω scans	θ_max = 27.5°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −15→14
T_min = 0.294, T_max = 1.000	k = −22→23
20508 measured reflections	l = −18→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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.113	H-atom parameters constrained
S = 1.07	w = 1/[σ²(F_o²) + (0.0581P)²] where P = (F_o² + 2F_c²)/3
6663 reflections	(Δ/σ)_max = 0.002
307 parameters	Δρ_max = 1.09 e Å⁻³
4 restraints	Δρ_min = −0.76 e Å⁻³

Crystal data top

[Au(C₉H₉ClNOS)(C₁₈H₃₃P)]	V = 2906.6 (4) Å³
M_r = 692.06	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 12.0513 (11) Å	µ = 5.30 mm⁻¹
b = 18.2460 (16) Å	T = 223 K
c = 13.9712 (12) Å	0.16 × 0.13 × 0.08 mm
β = 108.892 (2)°

Data collection top

Bruker SMART CCD diffractometer	6663 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2000)	5016 reflections with I > 2σ(I)
T_min = 0.294, T_max = 1.000	R_int = 0.045
20508 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.037	4 restraints
wR(F²) = 0.113	H-atom parameters constrained
S = 1.07	Δρ_max = 1.09 e Å⁻³
6663 reflections	Δρ_min = −0.76 e Å⁻³
307 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	Occ. (<1)
Au	0.529378 (18)	0.173673 (11)	0.875172 (14)	0.04429 (9)
Cl1	0.42395 (18)	0.22916 (13)	1.26094 (19)	0.1023 (7)
S1	0.59973 (15)	0.18353 (8)	1.04903 (11)	0.0560 (4)
P1	0.45520 (12)	0.16794 (7)	0.70427 (10)	0.0395 (3)
N1	0.5235 (5)	0.1057 (3)	1.1784 (4)	0.0663 (15)
C1	0.5164 (6)	0.1201 (3)	1.0884 (5)	0.0610 (16)
C2	0.6046 (6)	0.1433 (3)	1.2587 (4)	0.0581 (15)
C3	0.5696 (6)	0.2006 (4)	1.3065 (5)	0.0594 (15)
C4	0.6477 (7)	0.2369 (4)	1.3876 (5)	0.0692 (18)
H4	0.6220	0.2760	1.4190	0.083*
C5	0.7621 (7)	0.2153 (4)	1.4216 (5)	0.0707 (19)
H5	0.8159	0.2400	1.4762	0.085*
C6	0.7986 (7)	0.1581 (4)	1.3767 (5)	0.073 (2)
H6	0.8773	0.1428	1.4009	0.087*
C7	0.7210 (6)	0.1229 (4)	1.2964 (5)	0.0693 (17)
H7	0.7476	0.0837	1.2660	0.083*
O1A	0.4364 (5)	0.0846 (2)	1.0101 (3)	0.0862 (17)	0.50
C8A	0.3522 (11)	0.0437 (7)	1.0452 (10)	0.070 (4)	0.50
H8A1	0.3905	0.0004	1.0831	0.083*	0.50
H8A2	0.3253	0.0746	1.0907	0.083*	0.50
C9A	0.2477 (12)	0.0201 (8)	0.9560 (10)	0.078 (3)	0.50
H9A1	0.1995	0.0625	0.9281	0.116*	0.50
H9A2	0.2017	−0.0155	0.9785	0.116*	0.50
H9A3	0.2752	−0.0017	0.9045	0.116*	0.50
O1B	0.4364 (5)	0.0846 (2)	1.0101 (3)	0.0862 (17)	0.50
C8B	0.3756 (12)	0.0190 (5)	1.0270 (13)	0.070 (4)	0.50
H8B1	0.4211	−0.0080	1.0876	0.083*	0.50
H8B2	0.3530	−0.0137	0.9682	0.083*	0.50
C9B	0.2715 (13)	0.0587 (8)	1.0410 (12)	0.078 (3)	0.50
H9B1	0.2951	0.0823	1.1068	0.116*	0.50
H9B2	0.2094	0.0238	1.0367	0.116*	0.50
H9B3	0.2434	0.0955	0.9886	0.116*	0.50
C10	0.3110 (5)	0.1225 (4)	0.6683 (4)	0.0550 (14)
H10	0.3306	0.0707	0.6873	0.066*
C11	0.2437 (5)	0.1186 (3)	0.5555 (4)	0.0473 (12)
H11A	0.2281	0.1685	0.5285	0.057*
H11B	0.2924	0.0941	0.5210	0.057*
C12	0.1291 (6)	0.0781 (5)	0.5329 (5)	0.079 (2)
H12A	0.0834	0.0864	0.4617	0.094*
H12B	0.1461	0.0255	0.5413	0.094*
C13	0.0565 (6)	0.0979 (5)	0.5947 (5)	0.083 (2)
H13A	−0.0070	0.0621	0.5834	0.100*
H13B	0.0208	0.1460	0.5730	0.100*
C14	0.1252 (6)	0.1008 (4)	0.7069 (5)	0.0602 (16)
H14A	0.0757	0.1227	0.7428	0.072*
H14B	0.1441	0.0507	0.7321	0.072*
C15	0.2376 (6)	0.1444 (4)	0.7308 (5)	0.0644 (16)
H15A	0.2183	0.1966	0.7198	0.077*
H15B	0.2830	0.1378	0.8024	0.077*
C16	0.4327 (6)	0.2590 (3)	0.6469 (4)	0.0536 (14)
H16	0.3527	0.2735	0.6447	0.064*
C17	0.4317 (6)	0.2634 (4)	0.5363 (5)	0.0648 (17)
H17A	0.5074	0.2464	0.5328	0.078*
H17B	0.3707	0.2308	0.4943	0.078*
C18	0.4091 (9)	0.3410 (4)	0.4943 (7)	0.088 (3)
H18A	0.4169	0.3421	0.4266	0.106*
H18B	0.3287	0.3553	0.4880	0.106*
C19	0.4925 (10)	0.3944 (5)	0.5605 (9)	0.125 (4)
H19A	0.4737	0.4438	0.5324	0.150*
H19B	0.5724	0.3826	0.5620	0.150*
C20	0.4871 (10)	0.3932 (4)	0.6706 (8)	0.111 (3)
H20A	0.5444	0.4278	0.7129	0.134*
H20B	0.4088	0.4082	0.6702	0.134*
C21	0.5138 (9)	0.3155 (4)	0.7145 (7)	0.096 (3)
H21A	0.5953	0.3030	0.7222	0.115*
H21B	0.5048	0.3142	0.7818	0.115*
C22	0.5459 (5)	0.1134 (3)	0.6470 (4)	0.0447 (12)
H22	0.5119	0.1177	0.5725	0.054*
C23	0.6710 (6)	0.1432 (4)	0.6789 (6)	0.0699 (17)
H23A	0.6698	0.1934	0.6535	0.084*
H23B	0.7028	0.1449	0.7529	0.084*
C24	0.7504 (7)	0.0962 (5)	0.6385 (6)	0.086 (2)
H24A	0.7234	0.0985	0.5644	0.104*
H24B	0.8306	0.1155	0.6632	0.104*
C25	0.7504 (7)	0.0176 (5)	0.6717 (5)	0.090 (3)
H25A	0.8002	−0.0118	0.6433	0.109*
H25B	0.7828	0.0148	0.7456	0.109*
C26	0.6284 (7)	−0.0126 (4)	0.6372 (5)	0.0731 (19)
H26A	0.6300	−0.0631	0.6616	0.088*
H26B	0.5992	−0.0138	0.5631	0.088*
C27	0.5449 (6)	0.0325 (3)	0.6751 (5)	0.0597 (16)
H27A	0.5676	0.0279	0.7489	0.072*
H27B	0.4652	0.0131	0.6460	0.072*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Au	0.04234 (14)	0.04968 (14)	0.03387 (12)	−0.00306 (9)	0.00269 (9)	−0.00253 (8)
Cl1	0.0602 (12)	0.1215 (18)	0.1212 (18)	0.0090 (11)	0.0236 (12)	0.0049 (14)
S1	0.0604 (9)	0.0607 (9)	0.0355 (7)	−0.0221 (7)	−0.0003 (6)	−0.0001 (6)
P1	0.0340 (7)	0.0486 (7)	0.0338 (6)	−0.0022 (5)	0.0080 (5)	−0.0011 (5)
N1	0.070 (4)	0.070 (3)	0.046 (3)	−0.019 (3)	0.001 (3)	0.018 (2)
C1	0.064 (4)	0.048 (3)	0.053 (3)	−0.018 (3)	−0.007 (3)	0.012 (3)
C2	0.058 (4)	0.063 (4)	0.046 (3)	−0.013 (3)	0.007 (3)	0.017 (3)
C3	0.055 (4)	0.070 (4)	0.053 (3)	−0.002 (3)	0.018 (3)	0.020 (3)
C4	0.079 (5)	0.081 (5)	0.053 (4)	−0.016 (4)	0.030 (4)	−0.001 (3)
C5	0.073 (5)	0.095 (5)	0.038 (3)	−0.018 (4)	0.008 (3)	0.005 (3)
C6	0.060 (4)	0.098 (5)	0.048 (4)	0.008 (4)	−0.001 (3)	0.011 (3)
C7	0.065 (4)	0.073 (4)	0.058 (4)	0.008 (3)	0.005 (3)	0.008 (3)
O1A	0.101 (4)	0.070 (3)	0.057 (3)	−0.044 (3)	−0.019 (3)	0.014 (2)
C8A	0.094 (8)	0.018 (6)	0.074 (7)	−0.022 (6)	−0.003 (5)	−0.001 (6)
C9A	0.076 (7)	0.080 (7)	0.079 (7)	−0.030 (6)	0.027 (6)	−0.009 (5)
O1B	0.101 (4)	0.070 (3)	0.057 (3)	−0.044 (3)	−0.019 (3)	0.014 (2)
C8B	0.094 (8)	0.018 (6)	0.074 (7)	−0.022 (6)	−0.003 (5)	−0.001 (6)
C9B	0.076 (7)	0.080 (7)	0.079 (7)	−0.030 (6)	0.027 (6)	−0.009 (5)
C10	0.041 (3)	0.082 (4)	0.040 (3)	−0.010 (3)	0.010 (2)	−0.012 (3)
C11	0.043 (3)	0.057 (3)	0.038 (3)	−0.001 (2)	0.008 (2)	−0.007 (2)
C12	0.050 (4)	0.115 (6)	0.067 (4)	−0.016 (4)	0.013 (3)	−0.039 (4)
C13	0.058 (4)	0.119 (6)	0.070 (5)	−0.028 (4)	0.017 (4)	−0.022 (4)
C14	0.054 (4)	0.071 (4)	0.063 (4)	−0.015 (3)	0.029 (3)	−0.011 (3)
C15	0.057 (4)	0.091 (4)	0.045 (3)	−0.018 (4)	0.016 (3)	−0.008 (3)
C16	0.057 (4)	0.056 (3)	0.045 (3)	0.004 (3)	0.013 (3)	0.004 (3)
C17	0.073 (5)	0.070 (4)	0.057 (4)	0.000 (3)	0.028 (3)	0.018 (3)
C18	0.106 (7)	0.077 (5)	0.086 (6)	0.017 (5)	0.035 (5)	0.038 (4)
C19	0.123 (9)	0.087 (6)	0.162 (10)	−0.022 (6)	0.043 (8)	0.063 (6)
C20	0.136 (9)	0.052 (4)	0.126 (8)	−0.035 (5)	0.015 (7)	0.009 (5)
C21	0.116 (8)	0.065 (5)	0.090 (6)	−0.027 (4)	0.009 (6)	0.005 (4)
C22	0.040 (3)	0.055 (3)	0.041 (3)	0.002 (2)	0.014 (2)	0.000 (2)
C23	0.049 (4)	0.079 (4)	0.087 (5)	−0.002 (3)	0.029 (4)	−0.003 (4)
C24	0.055 (4)	0.112 (6)	0.097 (6)	0.022 (4)	0.033 (4)	−0.001 (5)
C25	0.079 (5)	0.133 (7)	0.060 (4)	0.061 (5)	0.022 (4)	0.007 (4)
C26	0.085 (5)	0.063 (4)	0.074 (4)	0.026 (4)	0.029 (4)	0.006 (3)
C27	0.071 (4)	0.058 (4)	0.055 (3)	0.016 (3)	0.028 (3)	0.009 (3)

Geometric parameters (Å, º) top

Au—P1	2.2648 (13)	C12—H12B	0.9800
Au—S1	2.3060 (14)	C13—C14	1.518 (9)
Cl1—C3	1.742 (7)	C13—H13A	0.9800
S1—C1	1.734 (6)	C13—H13B	0.9800
P1—C16	1.826 (6)	C14—C15	1.512 (8)
P1—C10	1.842 (6)	C14—H14A	0.9800
P1—C22	1.842 (5)	C14—H14B	0.9800
N1—C1	1.261 (8)	C15—H15A	0.9800
N1—C2	1.405 (8)	C15—H15B	0.9800
C1—O1B	1.364 (7)	C16—C21	1.520 (9)
C1—O1A	1.364 (7)	C16—C17	1.544 (8)
C2—C3	1.378 (10)	C16—H16	0.9900
C2—C7	1.380 (9)	C17—C18	1.523 (9)
C3—C4	1.384 (9)	C17—H17A	0.9800
C4—C5	1.363 (10)	C17—H17B	0.9800
C4—H4	0.9400	C18—C19	1.488 (13)
C5—C6	1.363 (10)	C18—H18A	0.9800
C5—H5	0.9400	C18—H18B	0.9800
C6—C7	1.366 (9)	C19—C20	1.561 (16)
C6—H6	0.9400	C19—H19A	0.9800
C7—H7	0.9400	C19—H19B	0.9800
O1A—C8A	1.466 (5)	C20—C21	1.537 (10)
C8A—C9A	1.519 (5)	C20—H20A	0.9800
C8A—H8A1	0.9800	C20—H20B	0.9800
C8A—H8A2	0.9800	C21—H21A	0.9800
C9A—H9A1	0.9700	C21—H21B	0.9800
C9A—H9A2	0.9700	C22—C23	1.528 (8)
C9A—H9A3	0.9700	C22—C27	1.529 (7)
O1B—C8B	1.461 (5)	C22—H22	0.9900
C8B—C9B	1.515 (5)	C23—C24	1.524 (9)
C8B—H8B1	0.9800	C23—H23A	0.9800
C8B—H8B2	0.9800	C23—H23B	0.9800
C9B—H9B1	0.9700	C24—C25	1.507 (10)
C9B—H9B2	0.9700	C24—H24A	0.9800
C9B—H9B3	0.9700	C24—H24B	0.9800
C10—C15	1.485 (8)	C25—C26	1.496 (11)
C10—C11	1.522 (7)	C25—H25A	0.9800
C10—H10	0.9900	C25—H25B	0.9800
C11—C12	1.507 (8)	C26—C27	1.521 (8)
C11—H11A	0.9800	C26—H26A	0.9800
C11—H11B	0.9800	C26—H26B	0.9800
C12—C13	1.460 (10)	C27—H27A	0.9800
C12—H12A	0.9800	C27—H27B	0.9800

P1—Au—S1	177.62 (5)	C13—C14—H14B	108.9
C1—S1—Au	103.2 (2)	H14A—C14—H14B	107.7
C16—P1—C10	107.2 (3)	C10—C15—C14	113.0 (5)
C16—P1—C22	109.0 (3)	C10—C15—H15A	109.0
C10—P1—C22	106.1 (3)	C14—C15—H15A	109.0
C16—P1—Au	111.85 (18)	C10—C15—H15B	109.0
C10—P1—Au	108.91 (18)	C14—C15—H15B	109.0
C22—P1—Au	113.32 (18)	H15A—C15—H15B	107.8
C1—N1—C2	119.9 (5)	C21—C16—C17	112.4 (6)
N1—C1—O1B	120.2 (5)	C21—C16—P1	111.7 (4)
N1—C1—O1A	120.2 (5)	C17—C16—P1	116.0 (4)
O1B—C1—O1A	0.0 (4)	C21—C16—H16	105.2
N1—C1—S1	126.6 (5)	C17—C16—H16	105.2
O1B—C1—S1	113.2 (4)	P1—C16—H16	105.2
O1A—C1—S1	113.2 (4)	C18—C17—C16	112.1 (6)
C3—C2—C7	116.9 (6)	C18—C17—H17A	109.2
C3—C2—N1	121.0 (6)	C16—C17—H17A	109.2
C7—C2—N1	122.1 (7)	C18—C17—H17B	109.2
C2—C3—C4	121.7 (6)	C16—C17—H17B	109.2
C2—C3—Cl1	118.7 (5)	H17A—C17—H17B	107.9
C4—C3—Cl1	119.6 (6)	C19—C18—C17	111.6 (7)
C5—C4—C3	119.3 (7)	C19—C18—H18A	109.3
C5—C4—H4	120.3	C17—C18—H18A	109.3
C3—C4—H4	120.3	C19—C18—H18B	109.3
C6—C5—C4	120.1 (6)	C17—C18—H18B	109.3
C6—C5—H5	119.9	H18A—C18—H18B	108.0
C4—C5—H5	119.9	C18—C19—C20	111.6 (7)
C5—C6—C7	120.1 (7)	C18—C19—H19A	109.3
C5—C6—H6	120.0	C20—C19—H19A	109.3
C7—C6—H6	120.0	C18—C19—H19B	109.3
C6—C7—C2	121.9 (7)	C20—C19—H19B	109.3
C6—C7—H7	119.1	H19A—C19—H19B	108.0
C2—C7—H7	119.1	C21—C20—C19	109.6 (8)
C1—O1A—C8A	111.1 (6)	C21—C20—H20A	109.7
C9A—C8A—O1A	110.5 (9)	C19—C20—H20A	109.7
C9A—C8A—H8A1	109.6	C21—C20—H20B	109.7
O1A—C8A—H8A1	109.6	C19—C20—H20B	109.7
C9A—C8A—H8A2	109.6	H20A—C20—H20B	108.2
O1A—C8A—H8A2	109.6	C16—C21—C20	111.6 (7)
H8A1—C8A—H8A2	108.1	C16—C21—H21A	109.3
C1—O1B—C8B	121.3 (8)	C20—C21—H21A	109.3
O1B—C8B—C9B	96.3 (9)	C16—C21—H21B	109.3
O1B—C8B—H8B1	112.5	C20—C21—H21B	109.3
C9B—C8B—H8B1	112.5	H21A—C21—H21B	108.0
O1B—C8B—H8B2	112.5	C23—C22—C27	111.0 (5)
C9B—C8B—H8B2	112.5	C23—C22—P1	110.4 (4)
H8B1—C8B—H8B2	110.0	C27—C22—P1	110.8 (4)
C8B—C9B—H9B1	109.5	C23—C22—H22	108.2
C8B—C9B—H9B2	109.5	C27—C22—H22	108.2
H9B1—C9B—H9B2	109.5	P1—C22—H22	108.2
C8B—C9B—H9B3	109.5	C24—C23—C22	111.7 (6)
H9B1—C9B—H9B3	109.5	C24—C23—H23A	109.3
H9B2—C9B—H9B3	109.5	C22—C23—H23A	109.3
C15—C10—C11	113.7 (5)	C24—C23—H23B	109.3
C15—C10—P1	114.0 (4)	C22—C23—H23B	109.3
C11—C10—P1	116.3 (4)	H23A—C23—H23B	107.9
C15—C10—H10	103.6	C25—C24—C23	111.0 (6)
C11—C10—H10	103.6	C25—C24—H24A	109.4
P1—C10—H10	103.6	C23—C24—H24A	109.4
C12—C11—C10	112.6 (5)	C25—C24—H24B	109.4
C12—C11—H11A	109.1	C23—C24—H24B	109.4
C10—C11—H11A	109.1	H24A—C24—H24B	108.0
C12—C11—H11B	109.1	C26—C25—C24	110.5 (6)
C10—C11—H11B	109.1	C26—C25—H25A	109.6
H11A—C11—H11B	107.8	C24—C25—H25A	109.6
C13—C12—C11	116.0 (5)	C26—C25—H25B	109.6
C13—C12—H12A	108.3	C24—C25—H25B	109.6
C11—C12—H12A	108.3	H25A—C25—H25B	108.1
C13—C12—H12B	108.3	C25—C26—C27	112.3 (6)
C11—C12—H12B	108.3	C25—C26—H26A	109.1
H12A—C12—H12B	107.4	C27—C26—H26A	109.1
C12—C13—C14	112.9 (6)	C25—C26—H26B	109.1
C12—C13—H13A	109.0	C27—C26—H26B	109.1
C14—C13—H13A	109.0	H26A—C26—H26B	107.9
C12—C13—H13B	109.0	C26—C27—C22	111.8 (5)
C14—C13—H13B	109.0	C26—C27—H27A	109.3
H13A—C13—H13B	107.8	C22—C27—H27A	109.3
C15—C14—C13	113.4 (5)	C26—C27—H27B	109.3
C15—C14—H14A	108.9	C22—C27—H27B	109.3
C13—C14—H14A	108.9	H27A—C27—H27B	107.9
C15—C14—H14B	108.9

P1—Au—S1—C1	95.0 (12)	C15—C10—C11—C12	−46.7 (8)
S1—Au—P1—C16	40.8 (12)	P1—C10—C11—C12	177.8 (5)
S1—Au—P1—C10	−77.6 (12)	C10—C11—C12—C13	46.4 (9)
S1—Au—P1—C22	164.6 (12)	C11—C12—C13—C14	−47.4 (10)
C2—N1—C1—O1B	−178.9 (6)	C12—C13—C14—C15	48.6 (9)
C2—N1—C1—O1A	−178.9 (6)	C11—C10—C15—C14	49.4 (8)
C2—N1—C1—S1	0.7 (10)	P1—C10—C15—C14	−174.1 (5)
Au—S1—C1—N1	179.9 (6)	C13—C14—C15—C10	−50.1 (8)
Au—S1—C1—O1B	−0.5 (6)	C10—P1—C16—C21	144.8 (6)
Au—S1—C1—O1A	−0.5 (6)	C22—P1—C16—C21	−100.7 (6)
C1—N1—C2—C3	100.5 (8)	Au—P1—C16—C21	25.4 (6)
C1—N1—C2—C7	−82.6 (8)	C10—P1—C16—C17	−84.6 (5)
C7—C2—C3—C4	1.0 (9)	C22—P1—C16—C17	29.9 (6)
N1—C2—C3—C4	178.0 (5)	Au—P1—C16—C17	156.0 (4)
C7—C2—C3—Cl1	179.3 (5)	C21—C16—C17—C18	−51.3 (9)
N1—C2—C3—Cl1	−3.6 (8)	P1—C16—C17—C18	178.4 (6)
C2—C3—C4—C5	−0.3 (9)	C16—C17—C18—C19	53.5 (10)
Cl1—C3—C4—C5	−178.6 (5)	C17—C18—C19—C20	−57.1 (11)
C3—C4—C5—C6	−0.7 (10)	C18—C19—C20—C21	57.7 (12)
C4—C5—C6—C7	1.0 (11)	C17—C16—C21—C20	52.8 (10)
C5—C6—C7—C2	−0.3 (11)	P1—C16—C21—C20	−174.8 (7)
C3—C2—C7—C6	−0.7 (10)	C19—C20—C21—C16	−55.0 (12)
N1—C2—C7—C6	−177.7 (6)	C16—P1—C22—C23	69.0 (5)
N1—C1—O1A—C8A	11.7 (11)	C10—P1—C22—C23	−175.8 (4)
O1B—C1—O1A—C8A	0 (39)	Au—P1—C22—C23	−56.3 (5)
S1—C1—O1A—C8A	−167.9 (7)	C16—P1—C22—C27	−167.6 (4)
C1—O1A—C8A—C9A	166.2 (10)	C10—P1—C22—C27	−52.4 (5)
N1—C1—O1B—C8B	−13.5 (12)	Au—P1—C22—C27	67.1 (4)
O1A—C1—O1B—C8B	0 (47)	C27—C22—C23—C24	52.9 (7)
S1—C1—O1B—C8B	166.9 (7)	P1—C22—C23—C24	176.2 (5)
C1—O1B—C8B—C9B	90.8 (12)	C22—C23—C24—C25	−56.3 (9)
C16—P1—C10—C15	−80.8 (5)	C23—C24—C25—C26	57.6 (8)
C22—P1—C10—C15	162.8 (5)	C24—C25—C26—C27	−56.9 (8)
Au—P1—C10—C15	40.4 (5)	C25—C26—C27—C22	54.2 (8)
C16—P1—C10—C11	54.5 (5)	C23—C22—C27—C26	−51.4 (7)
C22—P1—C10—C11	−61.9 (5)	P1—C22—C27—C26	−174.5 (5)
Au—P1—C10—C11	175.8 (4)

Experimental details

Crystal data
Chemical formula	[Au(C₉H₉ClNOS)(C₁₈H₃₃P)]
M_r	692.06
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	223
a, b, c (Å)	12.0513 (11), 18.2460 (16), 13.9712 (12)
β (°)	108.892 (2)
V (Å³)	2906.6 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	5.30
Crystal size (mm)	0.16 × 0.13 × 0.08

Data collection
Diffractometer	Bruker SMART CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2000)
T_min, T_max	0.294, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	20508, 6663, 5016
R_int	0.045
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.113, 1.07
No. of reflections	6663
No. of parameters	307
No. of restraints	4
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.09, −0.76

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 bond lengths (Å) top

Au—P1

2.2648 (13)

Au—S1

2.3060 (14)

Acknowledgements

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

References

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