[(Z)-O-Isopropyl N-phenyl­thio­car­bam­ato-κS](tricyclo­hexyl­phosphine-κP)gold(I)

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

doi:10.1107/S1600536810009906

metal-organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 66| Part 4| April 2010| Page m429

doi:10.1107/S1600536810009906

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[(Z)-O-Isopropyl N-phenylthiocarbamato-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 10 March 2010; accepted 16 March 2010; online 20 March 2010)

The Au atom in the title compound, [Au(C₁₀H₁₂NOS)(C₁₈H₃₃P)], is coordinated within an S,P-donor set that defines a slightly distorted linear geometry [S—Au—P = 174.54 (2)°], with the distortion due in part to a close intramolecular Au⋯O contact [3.1702 (16) Å]. In the crystal structure, molecules are arranged into supramolecular chains along the b axis mediated by C—H⋯O interactions.

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(C₁₀H₁₂NOS)(C₁₈H₃₃P)]
M_r = 671.65
Orthorhombic, P b c a
a = 19.3312 (10) Å
b = 15.1116 (7) Å
c = 19.811 (1) Å
V = 5787.3 (5) Å³
Z = 8
Mo Kα radiation
μ = 5.23 mm⁻¹
T = 193 K
0.23 × 0.18 × 0.16 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2000 ) T_min = 0.544, T_max = 1
39425 measured reflections
6645 independent reflections
5481 reflections with I > 2σ(I)
R_int = 0.040

Refinement

R[F² > 2σ(F²)] = 0.021
wR(F²) = 0.050
S = 1.03
6645 reflections
300 parameters
H-atom parameters constrained
Δρ_max = 0.99 e Å⁻³
Δρ_min = −0.69 e Å⁻³

Table 1
Selected bond lengths (Å)

Au—P1	2.2641 (6)
Au—S1	2.2998 (6)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4⋯O1ⁱ	0.95	2.48	3.367 (3)	156
Symmetry code: (i) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, z]$ .

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 datablocks global, I. DOI: 10.1107/S1600536810009906/ez2204sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810009906/ez2204Isup2.hkl

checkCIF report

Comment top

Systematic structural studies of molecules with the general formula R₃PAu[SC(OR')═NR''], for R, R' and R'' = alkyl and aryl, are motivated by crystal engineering and luminescence considerations (Ho et al. 2006; Ho & Tiekink, 2007; Kuan et al., 2008), and led to the synthesis and characterisation of the title compound, (I).

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 functioning as a thiolate as seen by the magnitudes of the C1—S1 [1.755 (2) Å] and C1═N1 [1.263 (3) Å] bond distances. The coordination geometry is distorted from the ideal linear [S—Au—P = 174.54 (2) °] owing to the close approach of the O1 atom [3.1702 (16) Å].

The most prominent interactions in the crystal structure are of the type C–H···O, Table 2, and these lead to the formation of supramolecular chains with glide symmetry along the b axis, 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)Ph 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 a supramolecular chain in (I) aligned along the b axis with the C–H···O interactions shown as orange dashed lines. Colour code: Au, orange; S, yellow; P, pink; O, red; N, blue; C, grey; and H, green.

[(Z)-O-Isopropyl N-phenylthiocarbamato- κS](tricyclohexylphosphine-κP)gold(I) top

Crystal data top

[Au(C₁₀H₁₂NOS)(C₁₈H₃₃P)]	F(000) = 2704
M_r = 671.65	D_x = 1.542 Mg m⁻³
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71069 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 6370 reflections
a = 19.3312 (10) Å	θ = 2.3–30.0°
b = 15.1116 (7) Å	µ = 5.23 mm⁻¹
c = 19.811 (1) Å	T = 193 K
V = 5787.3 (5) Å³	Block, colourless
Z = 8	0.23 × 0.18 × 0.16 mm

Data collection top

Bruker SMART CCD diffractometer	6645 independent reflections
Radiation source: fine-focus sealed tube	5481 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.040
ω scans	θ_max = 27.5°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −25→23
T_min = 0.544, T_max = 1	k = −19→12
39425 measured reflections	l = −25→25

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)] = 0.021	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.050	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0229P)²] where P = (F_o² + 2F_c²)/3
6645 reflections	(Δ/σ)_max = 0.005
300 parameters	Δρ_max = 0.99 e Å⁻³
0 restraints	Δρ_min = −0.69 e Å⁻³

Crystal data top

[Au(C₁₀H₁₂NOS)(C₁₈H₃₃P)]	V = 5787.3 (5) Å³
M_r = 671.65	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 19.3312 (10) Å	µ = 5.23 mm⁻¹
b = 15.1116 (7) Å	T = 193 K
c = 19.811 (1) Å	0.23 × 0.18 × 0.16 mm

Data collection top

Bruker SMART CCD diffractometer	6645 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2000)	5481 reflections with I > 2σ(I)
T_min = 0.544, T_max = 1	R_int = 0.040
39425 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.021	0 restraints
wR(F²) = 0.050	H-atom parameters constrained
S = 1.03	Δρ_max = 0.99 e Å⁻³
6645 reflections	Δρ_min = −0.69 e Å⁻³
300 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	0.187999 (5)	0.453847 (6)	0.925784 (4)	0.01954 (4)
S1	0.20150 (3)	0.58446 (4)	0.86767 (3)	0.02664 (14)
P1	0.17856 (3)	0.33212 (4)	0.99177 (3)	0.01871 (13)
O1	0.14511 (8)	0.48712 (10)	0.77343 (8)	0.0226 (4)
N1	0.13197 (11)	0.63489 (12)	0.75576 (10)	0.0248 (5)
C1	0.15504 (12)	0.57284 (15)	0.79206 (12)	0.0210 (5)
C2	0.14430 (13)	0.72399 (14)	0.77403 (12)	0.0233 (5)
C3	0.20992 (13)	0.76015 (16)	0.77533 (13)	0.0280 (6)
H3	0.2489	0.7237	0.7662	0.034*
C4	0.21951 (15)	0.84864 (16)	0.78978 (13)	0.0318 (6)
H4	0.2650	0.8726	0.7905	0.038*
C5	0.16365 (16)	0.90265 (17)	0.80318 (15)	0.0376 (7)
H5	0.1703	0.9633	0.8140	0.045*
C6	0.09806 (16)	0.86735 (16)	0.80066 (16)	0.0403 (7)
H6	0.0592	0.9041	0.8093	0.048*
C7	0.08822 (14)	0.77876 (16)	0.78567 (15)	0.0331 (6)
H7	0.0427	0.7554	0.7834	0.040*
C8	0.11414 (14)	0.47124 (16)	0.70740 (13)	0.0285 (6)
H8	0.0726	0.5099	0.7016	0.034*
C9	0.09212 (15)	0.37553 (16)	0.70929 (15)	0.0360 (7)
H9A	0.1330	0.3378	0.7146	0.054*
H9B	0.0684	0.3605	0.6671	0.054*
H9C	0.0606	0.3661	0.7474	0.054*
C10	0.16562 (18)	0.4903 (2)	0.65267 (16)	0.0490 (8)
H10A	0.1814	0.5517	0.6564	0.073*
H10B	0.1439	0.4812	0.6085	0.073*
H10C	0.2053	0.4503	0.6573	0.073*
C11	0.14793 (13)	0.23346 (15)	0.94552 (13)	0.0233 (5)
H11	0.1904	0.2027	0.9289	0.028*
C12	0.10620 (14)	0.25767 (17)	0.88274 (14)	0.0334 (6)
H12A	0.0627	0.2872	0.8964	0.040*
H12B	0.1330	0.2997	0.8547	0.040*
C13	0.08930 (16)	0.1754 (2)	0.84138 (16)	0.0463 (8)
H13A	0.0602	0.1924	0.8024	0.056*
H13B	0.1327	0.1495	0.8237	0.056*
C14	0.05156 (16)	0.1066 (2)	0.88319 (18)	0.0551 (10)
H14A	0.0057	0.1299	0.8965	0.066*
H14B	0.0441	0.0528	0.8557	0.066*
C15	0.09231 (18)	0.0828 (2)	0.94590 (18)	0.0515 (9)
H15A	0.1361	0.0537	0.9326	0.062*
H15B	0.0654	0.0403	0.9734	0.062*
C16	0.10861 (15)	0.16520 (16)	0.98846 (15)	0.0357 (7)
H16A	0.1371	0.1482	1.0279	0.043*
H16B	0.0650	0.1916	1.0053	0.043*
C17	0.11942 (13)	0.35252 (15)	1.06315 (11)	0.0214 (5)
H17	0.1117	0.2954	1.0874	0.026*
C18	0.15046 (15)	0.41908 (19)	1.11282 (14)	0.0356 (7)
H18A	0.1620	0.4746	1.0888	0.043*
H18B	0.1937	0.3947	1.1322	0.043*
C19	0.09894 (18)	0.4387 (2)	1.16965 (17)	0.0554 (9)
H19A	0.0914	0.3841	1.1963	0.066*
H19B	0.1190	0.4838	1.2001	0.066*
C20	0.03053 (18)	0.4714 (2)	1.14351 (18)	0.0548 (9)
H20A	0.0371	0.5290	1.1206	0.066*
H20B	−0.0016	0.4805	1.1818	0.066*
C21	−0.00063 (15)	0.4056 (2)	1.09443 (15)	0.0417 (7)
H21A	−0.0441	0.4300	1.0756	0.050*
H21B	−0.0119	0.3501	1.1185	0.050*
C22	0.04988 (13)	0.38596 (17)	1.03702 (13)	0.0314 (6)
H22A	0.0294	0.3408	1.0068	0.038*
H22B	0.0573	0.4405	1.0103	0.038*
C23	0.26327 (12)	0.30306 (15)	1.02821 (12)	0.0230 (5)
H23	0.2764	0.3532	1.0585	0.028*
C24	0.31875 (12)	0.29918 (18)	0.97299 (14)	0.0284 (6)
H24A	0.3078	0.2507	0.9411	0.034*
H24B	0.3188	0.3555	0.9474	0.034*
C25	0.39004 (14)	0.28369 (19)	1.00344 (15)	0.0395 (7)
H25A	0.4033	0.3355	1.0311	0.047*
H25B	0.4245	0.2773	0.9668	0.047*
C26	0.39063 (15)	0.2002 (2)	1.04759 (16)	0.0442 (8)
H26A	0.3820	0.1476	1.0190	0.053*
H26B	0.4368	0.1934	1.0686	0.053*
C27	0.33607 (15)	0.2054 (2)	1.10215 (15)	0.0396 (7)
H27A	0.3472	0.2546	1.1333	0.047*
H27B	0.3360	0.1497	1.1285	0.047*
C28	0.26457 (14)	0.22035 (17)	1.07165 (13)	0.0310 (6)
H28A	0.2516	0.1685	1.0438	0.037*
H28B	0.2301	0.2262	1.1083	0.037*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Au	0.02220 (6)	0.01907 (6)	0.01734 (6)	0.00080 (4)	−0.00015 (4)	0.00148 (3)
S1	0.0369 (4)	0.0185 (3)	0.0245 (3)	−0.0044 (3)	−0.0083 (3)	0.0021 (2)
P1	0.0202 (3)	0.0198 (3)	0.0161 (3)	−0.0002 (2)	−0.0012 (2)	0.0001 (2)
O1	0.0274 (9)	0.0162 (8)	0.0242 (9)	−0.0010 (7)	−0.0049 (8)	−0.0033 (7)
N1	0.0287 (12)	0.0197 (10)	0.0259 (12)	−0.0001 (9)	−0.0057 (9)	0.0009 (8)
C1	0.0187 (12)	0.0212 (12)	0.0232 (14)	−0.0003 (10)	0.0014 (10)	−0.0016 (10)
C2	0.0310 (14)	0.0197 (12)	0.0192 (13)	−0.0003 (10)	−0.0054 (11)	0.0041 (10)
C3	0.0295 (14)	0.0298 (14)	0.0247 (14)	−0.0020 (11)	−0.0020 (11)	0.0056 (11)
C4	0.0358 (15)	0.0314 (15)	0.0281 (15)	−0.0124 (12)	−0.0082 (12)	0.0076 (11)
C5	0.0568 (19)	0.0167 (13)	0.0392 (18)	−0.0072 (13)	−0.0184 (15)	0.0038 (11)
C6	0.0405 (17)	0.0220 (14)	0.058 (2)	0.0100 (12)	−0.0093 (15)	−0.0040 (13)
C7	0.0281 (14)	0.0227 (13)	0.0485 (19)	0.0004 (11)	−0.0079 (13)	0.0015 (12)
C8	0.0350 (15)	0.0251 (13)	0.0254 (15)	0.0007 (11)	−0.0057 (12)	−0.0045 (10)
C9	0.0396 (16)	0.0304 (15)	0.0381 (18)	−0.0103 (12)	−0.0052 (13)	−0.0067 (12)
C10	0.075 (2)	0.0394 (17)	0.0328 (18)	−0.0116 (17)	0.0153 (16)	−0.0100 (14)
C11	0.0220 (13)	0.0230 (13)	0.0249 (14)	−0.0017 (10)	0.0009 (10)	−0.0061 (10)
C12	0.0352 (15)	0.0384 (15)	0.0267 (15)	−0.0005 (12)	−0.0072 (12)	−0.0102 (12)
C13	0.0423 (18)	0.057 (2)	0.0397 (19)	0.0019 (15)	−0.0102 (14)	−0.0255 (15)
C14	0.0392 (19)	0.0485 (19)	0.078 (3)	−0.0093 (15)	−0.0070 (18)	−0.0400 (18)
C15	0.055 (2)	0.0299 (16)	0.070 (2)	−0.0126 (15)	0.0029 (18)	−0.0121 (16)
C16	0.0400 (16)	0.0259 (14)	0.0412 (18)	−0.0112 (12)	−0.0012 (14)	−0.0032 (12)
C17	0.0255 (13)	0.0223 (12)	0.0164 (13)	−0.0034 (10)	0.0029 (10)	−0.0017 (9)
C18	0.0363 (16)	0.0433 (16)	0.0272 (16)	−0.0026 (13)	0.0015 (13)	−0.0157 (13)
C19	0.056 (2)	0.078 (3)	0.0323 (19)	−0.0080 (18)	0.0096 (16)	−0.0249 (16)
C20	0.052 (2)	0.058 (2)	0.054 (2)	0.0009 (16)	0.0267 (18)	−0.0227 (16)
C21	0.0277 (16)	0.0544 (19)	0.0431 (18)	0.0026 (14)	0.0128 (13)	−0.0054 (15)
C22	0.0239 (14)	0.0415 (16)	0.0288 (16)	0.0039 (11)	0.0042 (11)	−0.0028 (11)
C23	0.0244 (13)	0.0255 (13)	0.0191 (13)	0.0029 (10)	−0.0034 (10)	−0.0001 (10)
C24	0.0231 (14)	0.0375 (15)	0.0248 (14)	0.0003 (11)	0.0024 (11)	0.0050 (11)
C25	0.0234 (15)	0.0557 (19)	0.0392 (18)	0.0025 (13)	0.0036 (13)	−0.0005 (14)
C26	0.0328 (17)	0.065 (2)	0.0351 (18)	0.0218 (15)	−0.0037 (14)	0.0056 (15)
C27	0.0382 (17)	0.0500 (19)	0.0305 (17)	0.0164 (14)	−0.0066 (14)	0.0087 (13)
C28	0.0320 (15)	0.0349 (15)	0.0260 (15)	0.0065 (12)	−0.0016 (12)	0.0091 (11)

Geometric parameters (Å, º) top

Au—P1	2.2641 (6)	C14—H14B	0.9900
Au—S1	2.2998 (6)	C15—C16	1.536 (4)
S1—C1	1.755 (2)	C15—H15A	0.9900
P1—C23	1.843 (2)	C15—H15B	0.9900
P1—C17	1.844 (2)	C16—H16A	0.9900
P1—C11	1.847 (2)	C16—H16B	0.9900
O1—C1	1.361 (3)	C17—C22	1.527 (3)
O1—C8	1.458 (3)	C17—C18	1.530 (3)
N1—C1	1.263 (3)	C17—H17	1.0000
N1—C2	1.414 (3)	C18—C19	1.532 (4)
C2—C3	1.382 (3)	C18—H18A	0.9900
C2—C7	1.383 (3)	C18—H18B	0.9900
C3—C4	1.380 (3)	C19—C20	1.504 (5)
C3—H3	0.9500	C19—H19A	0.9900
C4—C5	1.379 (4)	C19—H19B	0.9900
C4—H4	0.9500	C20—C21	1.515 (4)
C5—C6	1.377 (4)	C20—H20A	0.9900
C5—H5	0.9500	C20—H20B	0.9900
C6—C7	1.384 (3)	C21—C22	1.528 (4)
C6—H6	0.9500	C21—H21A	0.9900
C7—H7	0.9500	C21—H21B	0.9900
C8—C10	1.500 (4)	C22—H22A	0.9900
C8—C9	1.508 (3)	C22—H22B	0.9900
C8—H8	1.0000	C23—C28	1.518 (3)
C9—H9A	0.9800	C23—C24	1.533 (3)
C9—H9B	0.9800	C23—H23	1.0000
C9—H9C	0.9800	C24—C25	1.522 (4)
C10—H10A	0.9800	C24—H24A	0.9900
C10—H10B	0.9800	C24—H24B	0.9900
C10—H10C	0.9800	C25—C26	1.535 (4)
C11—C12	1.527 (3)	C25—H25A	0.9900
C11—C16	1.538 (3)	C25—H25B	0.9900
C11—H11	1.0000	C26—C27	1.512 (4)
C12—C13	1.524 (3)	C26—H26A	0.9900
C12—H12A	0.9900	C26—H26B	0.9900
C12—H12B	0.9900	C27—C28	1.525 (4)
C13—C14	1.517 (5)	C27—H27A	0.9900
C13—H13A	0.9900	C27—H27B	0.9900
C13—H13B	0.9900	C28—H28A	0.9900
C14—C15	1.515 (5)	C28—H28B	0.9900
C14—H14A	0.9900

P1—Au—S1	174.54 (2)	C15—C16—C11	110.0 (2)
C1—S1—Au	106.46 (8)	C15—C16—H16A	109.7
C23—P1—C17	106.88 (11)	C11—C16—H16A	109.7
C23—P1—C11	106.67 (11)	C15—C16—H16B	109.7
C17—P1—C11	108.45 (11)	C11—C16—H16B	109.7
C23—P1—Au	110.38 (8)	H16A—C16—H16B	108.2
C17—P1—Au	110.91 (8)	C22—C17—C18	110.2 (2)
C11—P1—Au	113.27 (8)	C22—C17—P1	109.94 (16)
C1—O1—C8	117.25 (17)	C18—C17—P1	111.10 (17)
C1—N1—C2	120.1 (2)	C22—C17—H17	108.5
N1—C1—O1	120.2 (2)	C18—C17—H17	108.5
N1—C1—S1	126.33 (19)	P1—C17—H17	108.5
O1—C1—S1	113.51 (16)	C17—C18—C19	110.2 (2)
C3—C2—C7	118.7 (2)	C17—C18—H18A	109.6
C3—C2—N1	122.4 (2)	C19—C18—H18A	109.6
C7—C2—N1	118.7 (2)	C17—C18—H18B	109.6
C4—C3—C2	120.7 (2)	C19—C18—H18B	109.6
C4—C3—H3	119.7	H18A—C18—H18B	108.1
C2—C3—H3	119.7	C20—C19—C18	112.5 (3)
C5—C4—C3	120.5 (3)	C20—C19—H19A	109.1
C5—C4—H4	119.7	C18—C19—H19A	109.1
C3—C4—H4	119.7	C20—C19—H19B	109.1
C6—C5—C4	119.0 (2)	C18—C19—H19B	109.1
C6—C5—H5	120.5	H19A—C19—H19B	107.8
C4—C5—H5	120.5	C19—C20—C21	110.8 (3)
C5—C6—C7	120.6 (3)	C19—C20—H20A	109.5
C5—C6—H6	119.7	C21—C20—H20A	109.5
C7—C6—H6	119.7	C19—C20—H20B	109.5
C2—C7—C6	120.5 (2)	C21—C20—H20B	109.5
C2—C7—H7	119.8	H20A—C20—H20B	108.1
C6—C7—H7	119.8	C20—C21—C22	110.6 (2)
O1—C8—C10	110.2 (2)	C20—C21—H21A	109.5
O1—C8—C9	104.6 (2)	C22—C21—H21A	109.5
C10—C8—C9	112.9 (2)	C20—C21—H21B	109.5
O1—C8—H8	109.7	C22—C21—H21B	109.5
C10—C8—H8	109.7	H21A—C21—H21B	108.1
C9—C8—H8	109.7	C17—C22—C21	112.0 (2)
C8—C9—H9A	109.5	C17—C22—H22A	109.2
C8—C9—H9B	109.5	C21—C22—H22A	109.2
H9A—C9—H9B	109.5	C17—C22—H22B	109.2
C8—C9—H9C	109.5	C21—C22—H22B	109.2
H9A—C9—H9C	109.5	H22A—C22—H22B	107.9
H9B—C9—H9C	109.5	C28—C23—C24	111.2 (2)
C8—C10—H10A	109.5	C28—C23—P1	115.66 (18)
C8—C10—H10B	109.5	C24—C23—P1	110.57 (17)
H10A—C10—H10B	109.5	C28—C23—H23	106.3
C8—C10—H10C	109.5	C24—C23—H23	106.3
H10A—C10—H10C	109.5	P1—C23—H23	106.3
H10B—C10—H10C	109.5	C25—C24—C23	110.9 (2)
C12—C11—C16	110.5 (2)	C25—C24—H24A	109.5
C12—C11—P1	112.33 (17)	C23—C24—H24A	109.5
C16—C11—P1	115.17 (18)	C25—C24—H24B	109.5
C12—C11—H11	106.0	C23—C24—H24B	109.5
C16—C11—H11	106.0	H24A—C24—H24B	108.1
P1—C11—H11	106.0	C24—C25—C26	111.0 (2)
C13—C12—C11	110.8 (2)	C24—C25—H25A	109.4
C13—C12—H12A	109.5	C26—C25—H25A	109.4
C11—C12—H12A	109.5	C24—C25—H25B	109.4
C13—C12—H12B	109.5	C26—C25—H25B	109.4
C11—C12—H12B	109.5	H25A—C25—H25B	108.0
H12A—C12—H12B	108.1	C27—C26—C25	111.1 (2)
C14—C13—C12	111.6 (2)	C27—C26—H26A	109.4
C14—C13—H13A	109.3	C25—C26—H26A	109.4
C12—C13—H13A	109.3	C27—C26—H26B	109.4
C14—C13—H13B	109.3	C25—C26—H26B	109.4
C12—C13—H13B	109.3	H26A—C26—H26B	108.0
H13A—C13—H13B	108.0	C26—C27—C28	110.9 (2)
C15—C14—C13	111.1 (2)	C26—C27—H27A	109.5
C15—C14—H14A	109.4	C28—C27—H27A	109.5
C13—C14—H14A	109.4	C26—C27—H27B	109.5
C15—C14—H14B	109.4	C28—C27—H27B	109.5
C13—C14—H14B	109.4	H27A—C27—H27B	108.1
H14A—C14—H14B	108.0	C23—C28—C27	111.2 (2)
C14—C15—C16	111.4 (3)	C23—C28—H28A	109.4
C14—C15—H15A	109.4	C27—C28—H28A	109.4
C16—C15—H15A	109.4	C23—C28—H28B	109.4
C14—C15—H15B	109.4	C27—C28—H28B	109.4
C16—C15—H15B	109.4	H28A—C28—H28B	108.0
H15A—C15—H15B	108.0

P1—Au—S1—C1	−165.2 (2)	C14—C15—C16—C11	−56.7 (3)
S1—Au—P1—C23	−58.3 (3)	C12—C11—C16—C15	56.9 (3)
S1—Au—P1—C17	59.9 (3)	P1—C11—C16—C15	−174.5 (2)
C2—N1—C1—O1	−177.9 (2)	C23—P1—C17—C22	174.41 (17)
C2—N1—C1—S1	1.6 (4)	C11—P1—C17—C22	−70.93 (19)
C8—O1—C1—N1	6.6 (3)	Au—P1—C17—C22	54.05 (18)
C8—O1—C1—S1	−173.04 (17)	C23—P1—C17—C18	52.1 (2)
Au—S1—C1—N1	157.6 (2)	C11—P1—C17—C18	166.76 (18)
Au—S1—C1—O1	−22.86 (18)	Au—P1—C17—C18	−68.26 (19)
C1—N1—C2—C3	64.9 (3)	C22—C17—C18—C19	54.9 (3)
C1—N1—C2—C7	−120.5 (3)	P1—C17—C18—C19	177.0 (2)
C7—C2—C3—C4	1.8 (4)	C17—C18—C19—C20	−56.2 (4)
N1—C2—C3—C4	176.4 (2)	C18—C19—C20—C21	56.6 (4)
C2—C3—C4—C5	0.0 (4)	C19—C20—C21—C22	−55.6 (4)
C3—C4—C5—C6	−1.2 (4)	C18—C17—C22—C21	−56.1 (3)
C4—C5—C6—C7	0.7 (4)	P1—C17—C22—C21	−178.89 (18)
C3—C2—C7—C6	−2.3 (4)	C20—C21—C22—C17	56.3 (3)
N1—C2—C7—C6	−177.1 (2)	C17—P1—C23—C28	61.4 (2)
C5—C6—C7—C2	1.0 (4)	C11—P1—C23—C28	−54.4 (2)
C1—O1—C8—C10	73.4 (3)	Au—P1—C23—C28	−177.88 (16)
C1—O1—C8—C9	−165.0 (2)	C17—P1—C23—C24	−171.08 (17)
C23—P1—C11—C12	−146.24 (18)	C11—P1—C23—C24	73.06 (19)
C17—P1—C11—C12	99.0 (2)	Au—P1—C23—C24	−50.38 (18)
Au—P1—C11—C12	−24.6 (2)	C28—C23—C24—C25	−55.4 (3)
C23—P1—C11—C16	86.1 (2)	P1—C23—C24—C25	174.72 (18)
C17—P1—C11—C16	−28.7 (2)	C23—C24—C25—C26	55.2 (3)
Au—P1—C11—C16	−152.29 (16)	C24—C25—C26—C27	−56.2 (3)
C16—C11—C12—C13	−56.7 (3)	C25—C26—C27—C28	56.4 (3)
P1—C11—C12—C13	173.13 (19)	C24—C23—C28—C27	55.9 (3)
C11—C12—C13—C14	56.0 (3)	P1—C23—C28—C27	−176.94 (19)
C12—C13—C14—C15	−55.4 (3)	C26—C27—C28—C23	−56.6 (3)
C13—C14—C15—C16	56.0 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···O1ⁱ	0.95	2.48	3.367 (3)	156

Symmetry code: (i) −x+1/2, y+1/2, z.

Experimental details

Crystal data
Chemical formula	[Au(C₁₀H₁₂NOS)(C₁₈H₃₃P)]
M_r	671.65
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	193
a, b, c (Å)	19.3312 (10), 15.1116 (7), 19.811 (1)
V (Å³)	5787.3 (5)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	5.23
Crystal size (mm)	0.23 × 0.18 × 0.16

Data collection
Diffractometer	Bruker SMART CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2000)
T_min, T_max	0.544, 1
No. of measured, independent and observed [I > 2σ(I)] reflections	39425, 6645, 5481
R_int	0.040
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.021, 0.050, 1.03
No. of reflections	6645
No. of parameters	300
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.99, −0.69

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

2.2641 (6)

Au—S1

2.2998 (6)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···O1ⁱ	0.95	2.48	3.367 (3)	156

Symmetry code: (i) −x+1/2, y+1/2, 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 m429

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

[(Z)-O-Iso­propyl N-phenyl­thio­car­bam­ato-κS](tri­cyclo­hexyl­phosphine-κP)gold(I)

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

metal-organic compounds

[(Z)-O-Isopropyl N-phenylthiocarbamato-κS](tricyclohexylphosphine-κP)gold(I)