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

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

doi:10.1107/S160053681000975X

metal-organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 66| Part 4| April 2010| Page m421

doi:10.1107/S160053681000975X

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[(Z)-O-Isopropyl N-(m-tolyl)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 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 & Tiekink (2007 ); Kuan et al. (2008 ). For the synthesis, see Hall et al. (1993 ).

Experimental

Crystal data

[Au(C₁₁H₁₄NOS)(C₁₈H₃₃P)]
M_r = 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 ) T_min = 0.445, T_max = 1.000
20885 measured reflections
6943 independent reflections
5710 reflections with I > 2σ(I)
R_int = 0.031

Refinement

R[F² > 2σ(F²)] = 0.028
wR(F²) = 0.072
S = 1.03
6943 reflections
308 parameters
H-atom parameters constrained
Δρ_max = 1.60 e Å⁻³
Δρ_min = −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	D⋯A	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); 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 datablock global. DOI: 10.1107/S160053681000975X/hg2660sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681000975X/hg2660Isup2.hkl

checkCIF report

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 C1═N1 [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.

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.
	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
M_r = 685.67	D_x = 1.503 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71069 Å
Hall symbol: -P 2ybc	Cell parameters from 993 reflections
a = 13.7415 (18) Å	θ = 2.4–26.7°
b = 13.3528 (18) Å	µ = 5.00 mm⁻¹
c = 16.788 (2) Å	T = 223 K
β = 100.308 (3)°	Block, colourless
V = 3030.7 (7) Å³	0.37 × 0.10 × 0.10 mm
Z = 4

Data collection top

Bruker SMART CCD diffractometer	6943 independent reflections
Radiation source: fine-focus sealed tube	5710 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.031
ω scans	θ_max = 27.5°, θ_min = 1.5°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −17→17
T_min = 0.445, T_max = 1.000	k = −12→17
20885 measured reflections	l = −21→20

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)] = 0.028	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.072	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0386P)²] where P = (F_o² + 2F_c²)/3
6943 reflections	(Δ/σ)_max = 0.001
308 parameters	Δρ_max = 1.60 e Å⁻³
0 restraints	Δρ_min = −0.40 e Å⁻³

Crystal data top

[Au(C₁₁H₁₄NOS)(C₁₈H₃₃P)]	V = 3030.7 (7) Å³
M_r = 685.67	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 13.7415 (18) Å	µ = 5.00 mm⁻¹
b = 13.3528 (18) Å	T = 223 K
c = 16.788 (2) Å	0.37 × 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)
T_min = 0.445, T_max = 1.000	R_int = 0.031
20885 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.028	0 restraints
wR(F²) = 0.072	H-atom parameters constrained
S = 1.03	Δρ_max = 1.60 e Å⁻³
6943 reflections	Δρ_min = −0.40 e Å⁻³
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

	x	y	z	U_iso*/U_eq
Au	0.009245 (9)	0.077062 (9)	0.342984 (7)	0.03840 (5)
S1	0.16091 (6)	0.15458 (6)	0.37674 (6)	0.0453 (2)
P1	−0.13794 (6)	−0.00461 (6)	0.32160 (5)	0.03605 (18)
O1	0.19821 (19)	0.00020 (18)	0.29116 (16)	0.0534 (6)
N1	0.3294 (2)	0.1077 (2)	0.3217 (2)	0.0532 (8)
C1	0.2414 (3)	0.0848 (2)	0.3270 (2)	0.0460 (8)
C2	0.3764 (2)	0.1942 (3)	0.3601 (3)	0.0531 (9)
C3	0.3875 (3)	0.2088 (3)	0.4421 (3)	0.0581 (10)
H3	0.3594	0.1628	0.4738	0.070*
C4	0.4409 (3)	0.2924 (4)	0.4799 (3)	0.0660 (11)
C5	0.4820 (3)	0.3578 (3)	0.4314 (4)	0.0733 (13)
H5	0.5176	0.4137	0.4549	0.088*
C6	0.4720 (3)	0.3428 (4)	0.3502 (3)	0.0733 (13)
H6	0.5005	0.3883	0.3184	0.088*
C7	0.4203 (3)	0.2612 (3)	0.3142 (3)	0.0640 (11)
H7	0.4148	0.2509	0.2582	0.077*
C8	0.4511 (4)	0.3060 (5)	0.5685 (3)	0.0981 (17)
H8A	0.5165	0.3317	0.5901	0.147*
H8B	0.4418	0.2422	0.5937	0.147*
H8C	0.4016	0.3531	0.5798	0.147*
C9	0.2533 (3)	−0.0593 (3)	0.2416 (3)	0.0610 (11)
H9	0.2894	−0.0142	0.2102	0.073*
C10	0.1759 (4)	−0.1171 (4)	0.1845 (3)	0.0847 (15)
H10A	0.1317	−0.0706	0.1515	0.127*
H10B	0.1384	−0.1587	0.2155	0.127*
H10C	0.2080	−0.1592	0.1498	0.127*
C11	0.3256 (4)	−0.1286 (4)	0.2928 (3)	0.0811 (14)
H11A	0.3755	−0.0893	0.3275	0.122*
H11B	0.3572	−0.1708	0.2579	0.122*
H11C	0.2907	−0.1701	0.3258	0.122*
C12	−0.2309 (3)	0.0592 (2)	0.3696 (2)	0.0421 (8)
H12	−0.2484	0.1216	0.3384	0.050*
C13	−0.1880 (3)	0.0913 (3)	0.4560 (2)	0.0511 (9)
H13A	−0.1282	0.1312	0.4558	0.061*
H13B	−0.1692	0.0316	0.4892	0.061*
C14	−0.2617 (3)	0.1526 (3)	0.4934 (3)	0.0649 (11)
H14A	−0.2330	0.1686	0.5497	0.078*
H14B	−0.2752	0.2158	0.4638	0.078*
C15	−0.3573 (3)	0.0959 (4)	0.4909 (3)	0.0715 (13)
H15A	−0.4048	0.1384	0.5121	0.086*
H15B	−0.3449	0.0365	0.5256	0.086*
C16	−0.4009 (3)	0.0637 (4)	0.4053 (3)	0.0778 (14)
H16A	−0.4200	0.1232	0.3719	0.093*
H16B	−0.4606	0.0238	0.4060	0.093*
C17	−0.3273 (2)	0.0023 (3)	0.3681 (3)	0.0568 (10)
H17A	−0.3135	−0.0606	0.3982	0.068*
H17B	−0.3563	−0.0144	0.3120	0.068*
C18	−0.1932 (2)	−0.0195 (2)	0.21456 (19)	0.0404 (7)
H18	−0.2501	−0.0659	0.2110	0.048*
C19	−0.2310 (3)	0.0793 (3)	0.1754 (2)	0.0519 (9)
H19A	−0.1764	0.1275	0.1809	0.062*
H19B	−0.2817	0.1067	0.2036	0.062*
C20	−0.2749 (4)	0.0657 (3)	0.0859 (3)	0.0641 (12)
H20A	−0.3348	0.0247	0.0810	0.077*
H20B	−0.2940	0.1314	0.0620	0.077*
C21	−0.2044 (3)	0.0170 (3)	0.0393 (2)	0.0670 (12)
H21A	−0.1498	0.0631	0.0360	0.080*
H21B	−0.2387	0.0032	−0.0160	0.080*
C22	−0.1630 (4)	−0.0807 (3)	0.0790 (2)	0.0602 (11)
H22A	−0.1121	−0.1066	0.0503	0.072*
H22B	−0.2161	−0.1305	0.0742	0.072*
C23	−0.1184 (3)	−0.0660 (3)	0.1681 (2)	0.0485 (9)
H23A	−0.0966	−0.1308	0.1922	0.058*
H23B	−0.0603	−0.0223	0.1726	0.058*
C24	−0.1207 (2)	−0.1309 (2)	0.36852 (19)	0.0373 (7)
H24	−0.1315	−0.1229	0.4249	0.045*
C25	−0.1948 (2)	−0.2105 (2)	0.3298 (2)	0.0412 (7)
H25A	−0.1854	−0.2234	0.2742	0.049*
H25B	−0.2624	−0.1860	0.3278	0.049*
C26	−0.1799 (3)	−0.3075 (3)	0.3788 (2)	0.0490 (8)
H26A	−0.1947	−0.2955	0.4330	0.059*
H26B	−0.2260	−0.3585	0.3524	0.059*
C27	−0.0745 (3)	−0.3458 (3)	0.3862 (2)	0.0537 (9)
H27A	−0.0660	−0.4060	0.4201	0.064*
H27B	−0.0616	−0.3640	0.3324	0.064*
C28	−0.0008 (3)	−0.2657 (3)	0.4234 (2)	0.0558 (10)
H28A	0.0668	−0.2903	0.4253	0.067*
H28B	−0.0096	−0.2522	0.4791	0.067*
C29	−0.0154 (2)	−0.1691 (3)	0.3743 (2)	0.0477 (8)
H29A	0.0312	−0.1183	0.4002	0.057*
H29B	−0.0018	−0.1814	0.3198	0.057*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Au	0.04093 (8)	0.03425 (8)	0.03913 (8)	−0.00328 (5)	0.00472 (5)	−0.00191 (5)
S1	0.0431 (4)	0.0385 (5)	0.0546 (5)	−0.0042 (4)	0.0096 (4)	−0.0074 (4)
P1	0.0378 (4)	0.0335 (4)	0.0355 (4)	0.0002 (3)	0.0028 (3)	−0.0008 (3)
O1	0.0592 (15)	0.0424 (14)	0.0606 (16)	−0.0018 (12)	0.0163 (12)	−0.0119 (12)
N1	0.0439 (17)	0.0524 (18)	0.064 (2)	0.0025 (15)	0.0108 (15)	0.0019 (15)
C1	0.050 (2)	0.039 (2)	0.047 (2)	0.0068 (15)	0.0062 (16)	0.0050 (14)
C2	0.0348 (17)	0.051 (2)	0.072 (3)	0.0081 (16)	0.0043 (17)	0.0029 (19)
C3	0.043 (2)	0.054 (2)	0.076 (3)	0.0027 (17)	0.0061 (19)	0.000 (2)
C4	0.043 (2)	0.071 (3)	0.079 (3)	0.006 (2)	0.001 (2)	−0.007 (2)
C5	0.048 (2)	0.054 (3)	0.113 (4)	0.0004 (19)	0.002 (3)	0.002 (3)
C6	0.050 (2)	0.065 (3)	0.101 (4)	−0.002 (2)	0.004 (2)	0.020 (3)
C7	0.040 (2)	0.066 (3)	0.084 (3)	0.0013 (19)	0.0061 (19)	0.016 (2)
C8	0.080 (3)	0.115 (5)	0.098 (4)	−0.010 (3)	0.013 (3)	−0.025 (3)
C9	0.075 (3)	0.046 (2)	0.066 (3)	0.010 (2)	0.025 (2)	−0.0031 (18)
C10	0.114 (4)	0.063 (3)	0.079 (3)	0.008 (3)	0.022 (3)	−0.022 (3)
C11	0.100 (4)	0.068 (3)	0.079 (3)	0.022 (3)	0.026 (3)	0.001 (2)
C12	0.0438 (19)	0.0367 (19)	0.0438 (19)	0.0081 (14)	0.0025 (15)	−0.0008 (14)
C13	0.054 (2)	0.052 (2)	0.048 (2)	0.0014 (17)	0.0096 (17)	−0.0102 (16)
C14	0.077 (3)	0.060 (3)	0.062 (3)	0.011 (2)	0.023 (2)	−0.010 (2)
C15	0.064 (3)	0.079 (3)	0.077 (3)	0.023 (2)	0.026 (2)	−0.006 (2)
C16	0.046 (2)	0.101 (4)	0.089 (4)	0.017 (2)	0.017 (2)	−0.005 (3)
C17	0.0386 (19)	0.067 (3)	0.063 (2)	0.0069 (18)	0.0053 (17)	−0.008 (2)
C18	0.0428 (17)	0.0397 (19)	0.0358 (17)	−0.0096 (14)	−0.0004 (13)	0.0027 (13)
C19	0.060 (2)	0.045 (2)	0.047 (2)	−0.0031 (17)	0.0004 (17)	0.0100 (15)
C20	0.077 (3)	0.055 (3)	0.051 (2)	−0.015 (2)	−0.014 (2)	0.0186 (18)
C21	0.096 (3)	0.061 (3)	0.039 (2)	−0.030 (2)	−0.001 (2)	0.0029 (18)
C22	0.092 (3)	0.052 (2)	0.035 (2)	−0.016 (2)	0.008 (2)	−0.0033 (16)
C23	0.061 (2)	0.046 (2)	0.0375 (19)	−0.0088 (17)	0.0063 (16)	−0.0052 (14)
C24	0.0418 (17)	0.0330 (17)	0.0365 (17)	−0.0006 (14)	0.0049 (13)	0.0002 (13)
C25	0.0474 (18)	0.0379 (19)	0.0371 (17)	−0.0019 (15)	0.0046 (14)	0.0002 (13)
C26	0.063 (2)	0.0391 (19)	0.045 (2)	−0.0057 (17)	0.0084 (17)	0.0003 (15)
C27	0.077 (3)	0.0328 (19)	0.052 (2)	0.0086 (18)	0.0120 (19)	0.0050 (15)
C28	0.058 (2)	0.044 (2)	0.063 (2)	0.0100 (18)	0.0037 (19)	0.0075 (18)
C29	0.0426 (18)	0.041 (2)	0.058 (2)	0.0021 (15)	0.0032 (16)	0.0055 (16)

Geometric parameters (Å, º) top

Au—P1	2.2692 (9)	C15—C16	1.517 (7)
Au—S1	2.3051 (9)	C15—H15A	0.9800
S1—C1	1.766 (4)	C15—H15B	0.9800
P1—C12	1.837 (4)	C16—C17	1.521 (5)
P1—C18	1.832 (3)	C16—H16A	0.9800
P1—C24	1.858 (3)	C16—H16B	0.9800
O1—C1	1.365 (4)	C17—H17A	0.9800
O1—C9	1.456 (5)	C17—H17B	0.9800
N1—C1	1.266 (5)	C18—C19	1.524 (5)
N1—C2	1.420 (5)	C18—C23	1.529 (5)
C2—C3	1.372 (6)	C18—H18	0.9900
C2—C7	1.387 (6)	C19—C20	1.527 (5)
C3—C4	1.421 (6)	C19—H19A	0.9800
C3—H3	0.9400	C19—H19B	0.9800
C4—C5	1.383 (6)	C20—C21	1.498 (7)
C4—C8	1.480 (7)	C20—H20A	0.9800
C5—C6	1.359 (7)	C20—H20B	0.9800
C5—H5	0.9400	C21—C22	1.529 (6)
C6—C7	1.379 (6)	C21—H21A	0.9800
C6—H6	0.9400	C21—H21B	0.9800
C7—H7	0.9400	C22—C23	1.525 (5)
C8—H8A	0.9700	C22—H22A	0.9800
C8—H8B	0.9700	C22—H22B	0.9800
C8—H8C	0.9700	C23—H23A	0.9800
C9—C11	1.509 (6)	C23—H23B	0.9800
C9—C10	1.511 (7)	C24—C29	1.522 (4)
C9—H9	0.9900	C24—C25	1.534 (4)
C10—H10A	0.9700	C24—H24	0.9900
C10—H10B	0.9700	C25—C26	1.529 (5)
C10—H10C	0.9700	C25—H25A	0.9800
C11—H11A	0.9700	C25—H25B	0.9800
C11—H11B	0.9700	C26—C27	1.521 (5)
C11—H11C	0.9700	C26—H26A	0.9800
C12—C17	1.524 (5)	C26—H26B	0.9800
C12—C13	1.527 (5)	C27—C28	1.528 (5)
C12—H12	0.9900	C27—H27A	0.9800
C13—C14	1.522 (5)	C27—H27B	0.9800
C13—H13A	0.9800	C28—C29	1.525 (5)
C13—H13B	0.9800	C28—H28A	0.9800
C14—C15	1.511 (6)	C28—H28B	0.9800
C14—H14A	0.9800	C29—H29A	0.9800
C14—H14B	0.9800	C29—H29B	0.9800

P1—Au—S1	174.73 (3)	C15—C16—H16B	109.4
C1—S1—Au	105.20 (13)	C17—C16—H16B	109.4
C12—P1—C18	106.37 (16)	H16A—C16—H16B	108.0
C12—P1—C24	106.32 (16)	C12—C17—C16	111.4 (3)
C18—P1—C24	108.42 (15)	C12—C17—H17A	109.4
C12—P1—Au	112.19 (12)	C16—C17—H17A	109.4
C18—P1—Au	114.12 (11)	C12—C17—H17B	109.4
C24—P1—Au	109.07 (10)	C16—C17—H17B	109.4
C1—O1—C9	118.3 (3)	H17A—C17—H17B	108.0
C1—N1—C2	121.8 (3)	C19—C18—C23	109.9 (3)
N1—C1—O1	121.0 (3)	C19—C18—P1	112.2 (2)
N1—C1—S1	126.4 (3)	C23—C18—P1	110.2 (2)
O1—C1—S1	112.7 (3)	C19—C18—H18	108.1
C3—C2—N1	122.1 (4)	C23—C18—H18	108.1
C3—C2—C7	119.0 (4)	P1—C18—H18	108.1
N1—C2—C7	118.7 (4)	C18—C19—C20	111.4 (3)
C2—C3—C4	121.1 (4)	C18—C19—H19A	109.3
C2—C3—H3	119.5	C20—C19—H19A	109.3
C4—C3—H3	119.5	C18—C19—H19B	109.3
C5—C4—C3	117.7 (5)	C20—C19—H19B	109.3
C5—C4—C8	122.7 (5)	H19A—C19—H19B	108.0
C3—C4—C8	119.6 (5)	C21—C20—C19	112.8 (4)
C6—C5—C4	121.3 (5)	C21—C20—H20A	109.0
C6—C5—H5	119.4	C19—C20—H20A	109.0
C4—C5—H5	119.4	C21—C20—H20B	109.0
C5—C6—C7	120.5 (5)	C19—C20—H20B	109.0
C5—C6—H6	119.7	H20A—C20—H20B	107.8
C7—C6—H6	119.7	C20—C21—C22	111.6 (3)
C6—C7—C2	120.5 (5)	C20—C21—H21A	109.3
C6—C7—H7	119.8	C22—C21—H21A	109.3
C2—C7—H7	119.8	C20—C21—H21B	109.3
C4—C8—H8A	109.5	C22—C21—H21B	109.3
C4—C8—H8B	109.5	H21A—C21—H21B	108.0
H8A—C8—H8B	109.5	C21—C22—C23	111.8 (3)
C4—C8—H8C	109.5	C21—C22—H22A	109.3
H8A—C8—H8C	109.5	C23—C22—H22A	109.3
H8B—C8—H8C	109.5	C21—C22—H22B	109.3
O1—C9—C11	111.5 (4)	C23—C22—H22B	109.3
O1—C9—C10	105.2 (4)	H22A—C22—H22B	107.9
C11—C9—C10	111.4 (4)	C18—C23—C22	111.4 (3)
O1—C9—H9	109.5	C18—C23—H23A	109.4
C11—C9—H9	109.5	C22—C23—H23A	109.4
C10—C9—H9	109.5	C18—C23—H23B	109.4
C9—C10—H10A	109.5	C22—C23—H23B	109.4
C9—C10—H10B	109.5	H23A—C23—H23B	108.0
H10A—C10—H10B	109.5	C29—C24—C25	110.2 (3)
C9—C10—H10C	109.5	C29—C24—P1	112.3 (2)
H10A—C10—H10C	109.5	C25—C24—P1	115.1 (2)
H10B—C10—H10C	109.5	C29—C24—H24	106.2
C9—C11—H11A	109.5	C25—C24—H24	106.2
C9—C11—H11B	109.5	P1—C24—H24	106.2
H11A—C11—H11B	109.5	C24—C25—C26	110.1 (3)
C9—C11—H11C	109.5	C24—C25—H25A	109.6
H11A—C11—H11C	109.5	C26—C25—H25A	109.6
H11B—C11—H11C	109.5	C24—C25—H25B	109.6
C17—C12—C13	110.0 (3)	C26—C25—H25B	109.6
C17—C12—P1	115.6 (2)	H25A—C25—H25B	108.1
C13—C12—P1	111.5 (2)	C27—C26—C25	111.3 (3)
C17—C12—H12	106.4	C27—C26—H26A	109.4
C13—C12—H12	106.4	C25—C26—H26A	109.4
P1—C12—H12	106.4	C27—C26—H26B	109.4
C12—C13—C14	111.8 (3)	C25—C26—H26B	109.4
C12—C13—H13A	109.3	H26A—C26—H26B	108.0
C14—C13—H13A	109.3	C28—C27—C26	110.5 (3)
C12—C13—H13B	109.3	C28—C27—H27A	109.6
C14—C13—H13B	109.3	C26—C27—H27A	109.6
H13A—C13—H13B	107.9	C28—C27—H27B	109.6
C15—C14—C13	111.0 (3)	C26—C27—H27B	109.6
C15—C14—H14A	109.4	H27A—C27—H27B	108.1
C13—C14—H14A	109.4	C27—C28—C29	110.9 (3)
C15—C14—H14B	109.4	C27—C28—H28A	109.5
C13—C14—H14B	109.4	C29—C28—H28A	109.5
H14A—C14—H14B	108.0	C27—C28—H28B	109.5
C14—C15—C16	111.3 (4)	C29—C28—H28B	109.5
C14—C15—H15A	109.4	H28A—C28—H28B	108.0
C16—C15—H15A	109.4	C24—C29—C28	110.5 (3)
C14—C15—H15B	109.4	C24—C29—H29A	109.6
C16—C15—H15B	109.4	C28—C29—H29A	109.6
H15A—C15—H15B	108.0	C24—C29—H29B	109.6
C15—C16—C17	111.3 (4)	C28—C29—H29B	109.6
C15—C16—H16A	109.4	H29A—C29—H29B	108.1
C17—C16—H16A	109.4

P1—Au—S1—C1	107.5 (3)	C13—C14—C15—C16	−55.5 (5)
S1—Au—P1—C12	74.2 (3)	C14—C15—C16—C17	55.8 (5)
S1—Au—P1—C18	−164.8 (3)	C13—C12—C17—C16	55.6 (4)
S1—Au—P1—C24	−43.3 (3)	P1—C12—C17—C16	−177.1 (3)
C2—N1—C1—O1	−178.5 (3)	C15—C16—C17—C12	−56.1 (5)
C2—N1—C1—S1	2.8 (6)	C12—P1—C18—C19	53.4 (3)
C9—O1—C1—N1	−4.5 (5)	C24—P1—C18—C19	167.4 (3)
C9—O1—C1—S1	174.3 (3)	Au—P1—C18—C19	−70.8 (3)
Au—S1—C1—N1	171.7 (3)	C12—P1—C18—C23	176.2 (2)
Au—S1—C1—O1	−7.1 (3)	C24—P1—C18—C23	−69.8 (3)
C1—N1—C2—C3	58.2 (5)	Au—P1—C18—C23	52.0 (2)
C1—N1—C2—C7	−127.9 (4)	C23—C18—C19—C20	55.8 (4)
N1—C2—C3—C4	175.5 (3)	P1—C18—C19—C20	178.8 (3)
C7—C2—C3—C4	1.6 (5)	C18—C19—C20—C21	−54.8 (5)
C2—C3—C4—C5	−0.6 (6)	C19—C20—C21—C22	52.5 (4)
C2—C3—C4—C8	179.7 (4)	C20—C21—C22—C23	−52.9 (5)
C3—C4—C5—C6	−0.1 (6)	C19—C18—C23—C22	−56.7 (4)
C8—C4—C5—C6	179.5 (4)	P1—C18—C23—C22	179.2 (2)
C4—C5—C6—C7	−0.1 (7)	C21—C22—C23—C18	55.4 (5)
C5—C6—C7—C2	1.1 (6)	C12—P1—C24—C29	−147.5 (2)
C3—C2—C7—C6	−1.8 (6)	C18—P1—C24—C29	98.5 (3)
N1—C2—C7—C6	−175.9 (3)	Au—P1—C24—C29	−26.4 (3)
C1—O1—C9—C11	82.5 (5)	C12—P1—C24—C25	85.2 (3)
C1—O1—C9—C10	−156.6 (4)	C18—P1—C24—C25	−28.8 (3)
C18—P1—C12—C17	62.6 (3)	Au—P1—C24—C25	−153.6 (2)
C24—P1—C12—C17	−52.8 (3)	C29—C24—C25—C26	57.6 (4)
Au—P1—C12—C17	−172.0 (2)	P1—C24—C25—C26	−174.1 (2)
C18—P1—C12—C13	−170.8 (2)	C24—C25—C26—C27	−57.0 (4)
C24—P1—C12—C13	73.8 (3)	C25—C26—C27—C28	56.3 (4)
Au—P1—C12—C13	−45.4 (3)	C26—C27—C28—C29	−56.4 (4)
C17—C12—C13—C14	−55.7 (4)	C25—C24—C29—C28	−58.0 (4)
P1—C12—C13—C14	174.7 (3)	P1—C24—C29—C28	172.1 (3)
C12—C13—C14—C15	55.9 (5)	C27—C28—C29—C24	57.5 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C16—H16a···Cgⁱ	0.98	2.98	3.655 (5)	127

Symmetry code: (i) x−1, y, z.

Experimental details

Crystal data
Chemical formula	[Au(C₁₁H₁₄NOS)(C₁₈H₃₃P)]
M_r	685.67
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	223
a, b, c (Å)	13.7415 (18), 13.3528 (18), 16.788 (2)
β (°)	100.308 (3)
V (Å³)	3030.7 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	5.00
Crystal size (mm)	0.37 × 0.10 × 0.10

Data collection
Diffractometer	Bruker SMART CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2000)
T_min, T_max	0.445, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	20885, 6943, 5710
R_int	0.031
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.028, 0.072, 1.03
No. of reflections	6943
No. of parameters	308
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	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—P1	2.2692 (9)	Au—S1	2.3051 (9)

P1—Au—S1	174.73 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C16—H16a···Cgⁱ	0.98	2.98	3.655 (5)	127

Symmetry code: (i) x−1, y, z.

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, USA. Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals 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. (2010). publCIF. In preparation. Google Scholar

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Volume 66| Part 4| April 2010| Page m421

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

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

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Experimental

Crystal data

Data collection

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Supporting information

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