[(Z)-O-Ethyl-N-propyl­thio­carbamato-κS](triphenyl­phosphine-κP)gold(I)

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

doi:10.1107/S1600536809047254

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 12| December 2009| Page m1571

doi:10.1107/S1600536809047254

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[(Z)-O-Ethyl-N-propylthiocarbamato-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 8 November 2009; accepted 9 November 2009; online 14 November 2009)

The title compound, [Au(C₆H₁₂NOS)(C₁₈H₁₅P)], features a linear S,P-donor set about the central Au atom with a deviation from linearity [S—Au—P = 176.66 (5)°] due to an intramolecular Au⋯O contact [2.991 (5) Å]. Supramolecular dimers are formed in the crystal structure mediated by C—H⋯N interactions.

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 a description of phenyl embraces, see: Dance & Scudder (2009 ).

Experimental

Crystal data

[Au(C₆H₁₂NOS)(C₁₈H₁₅P)]
M_r = 605.46
Monoclinic, P 2₁ /n
a = 8.5822 (6) Å
b = 18.2036 (13) Å
c = 15.6893 (12) Å
β = 102.001 (2)°
V = 2397.5 (3) Å³
Z = 4
Mo Kα radiation
μ = 6.30 mm⁻¹
T = 223 K
0.16 × 0.05 × 0.04 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS, Bruker, 2000 ) T_min = 0.439, T_max = 1
16839 measured reflections
5496 independent reflections
4350 reflections with I > 2σ(I)
R_int = 0.042

Refinement

R[F² > 2σ(F²)] = 0.035
wR(F²) = 0.098
S = 1.07
5496 reflections
262 parameters
H-atom parameters constrained
Δρ_max = 1.19 e Å⁻³
Δρ_min = −0.63 e Å⁻³

Table 1
Selected bond lengths (Å)

Au—S1	2.2980 (14)
Au—P1	2.2561 (14)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8⋯N1ⁱ	0.94	2.54	3.433 (9)	159
Symmetry code: (i) -x, -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: DIAMOND (Brandenburg, 2006 ); software used to prepare material for publication: publCIF (Westrip, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809047254/hg2586sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809047254/hg2586Isup2.hkl

checkCIF report

Comment top

As a part of systematic studies of phosphinegold(I) thiocarbamides (Ho et al. 2006; Ho & Tiekink, 2007; Kuan et al., 2008), the title compound, Ph₃Au[SC(OEt)NC₃H₇], was synthesized.

The gold atom exists in the expected linear geometry defined by a SP donor set, Table 1 and Fig. 1, and the deviation from linearity [S1–Au–P1 is 176.66 (5) Å] is traced to the close approach of the O1 atom to Au [Au···O = 2.991 (5) Å]. The anion, with C1—S1 and C1—N1 bond distances of 1.765 (7) and 1.262 (8)Å, respectively, coordinates as a thiolate; the configuration about the double bond is Z.

In the crystal structure of (I), supramolecular dimers are formed owing to the presence of C–H···N interactions, Table 2 and Fig. 2. Dimers are connected by sixfold phenyl embraces with a P1···P1ⁱ separation of 6.836 (2) Å for i: -x, -y, 1 - z (Dance & Scudder, 2009). These cooperate with C–H···π interactions [C4–H4c···Cgⁱⁱ = 2.97 Å, C4···Cgⁱⁱ = 3.827 (11) Å with an angle at H4c = 148° for ii: 1/2 + x, 1/2 - y, -1/2 + z, where Cg is the ring centroid of C13—C18] to consolidate the crystal structure.

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 a description of phenyl embraces, see: Dance & Scudder (2009).

Experimental top

Compound (I) was prepared following the standard literature procedure from the reaction of Ph₃AuCl and EtOC(S)N(H)C₃H₇ 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.
	Fig. 2. Supramolecular dimer in (I) mediated by C—H···N contacts (orange dashed lines). Colour code: Au, orange; S, yellow; P, pink; O, red; N, blue; C, grey; and H, green.

[(Z)-O-Ethyl-N-propylthiocarbamato- κS](triphenylphosphine-κP)gold(I) top

Crystal data top

[Au(C₆H₁₂NOS)(C₁₈H₁₅P)]	F(000) = 1184
M_r = 605.46	D_x = 1.677 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71069 Å
Hall symbol: -P 2yn	Cell parameters from 3440 reflections
a = 8.5822 (6) Å	θ = 2.3–24.6°
b = 18.2036 (13) Å	µ = 6.30 mm⁻¹
c = 15.6893 (12) Å	T = 223 K
β = 102.001 (2)°	Block, colourless
V = 2397.5 (3) Å³	0.16 × 0.05 × 0.04 mm
Z = 4

Data collection top

Bruker SMART CCD diffractometer	5496 independent reflections
Radiation source: fine-focus sealed tube	4350 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.042
ω scans	θ_max = 27.5°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS, Bruker, 2000)	h = −9→11
T_min = 0.439, T_max = 1	k = −23→20
16839 measured reflections	l = −19→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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.098	H-atom parameters constrained
S = 1.07	w = 1/[σ²(F_o²) + (0.0474P)² + 0.1712P] where P = (F_o² + 2F_c²)/3
5496 reflections	(Δ/σ)_max < 0.001
262 parameters	Δρ_max = 1.19 e Å⁻³
0 restraints	Δρ_min = −0.63 e Å⁻³

Crystal data top

[Au(C₆H₁₂NOS)(C₁₈H₁₅P)]	V = 2397.5 (3) Å³
M_r = 605.46	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 8.5822 (6) Å	µ = 6.30 mm⁻¹
b = 18.2036 (13) Å	T = 223 K
c = 15.6893 (12) Å	0.16 × 0.05 × 0.04 mm
β = 102.001 (2)°

Data collection top

Bruker SMART CCD diffractometer	5496 independent reflections
Absorption correction: multi-scan (SADABS, Bruker, 2000)	4350 reflections with I > 2σ(I)
T_min = 0.439, T_max = 1	R_int = 0.042
16839 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.035	0 restraints
wR(F²) = 0.098	H-atom parameters constrained
S = 1.07	Δρ_max = 1.19 e Å⁻³
5496 reflections	Δρ_min = −0.63 e Å⁻³
262 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	0.14256 (2)	0.109862 (11)	0.186783 (14)	0.03589 (9)
S1	0.22776 (17)	0.15331 (8)	0.06673 (10)	0.0419 (3)
P1	0.07358 (15)	0.06794 (7)	0.30913 (9)	0.0332 (3)
O1	−0.0549 (5)	0.10164 (18)	0.0059 (3)	0.0400 (9)
N1	0.0878 (7)	0.1174 (3)	−0.0998 (4)	0.0607 (15)
C1	0.0790 (7)	0.1216 (3)	−0.0206 (4)	0.0423 (13)
C2	0.2390 (10)	0.1360 (6)	−0.1259 (5)	0.085 (3)
H2A	0.3195	0.1473	−0.0734	0.102*
H2B	0.2759	0.0929	−0.1535	0.102*
C3	0.2276 (11)	0.1954 (5)	−0.1832 (8)	0.115 (4)
H3A	0.2024	0.2400	−0.1538	0.138*
H3B	0.1406	0.1866	−0.2335	0.138*
C4	0.3849 (12)	0.2072 (6)	−0.2153 (7)	0.108 (3)
H4A	0.3752	0.2505	−0.2521	0.161*
H4B	0.4058	0.1647	−0.2484	0.161*
H4C	0.4720	0.2139	−0.1655	0.161*
C5	−0.1837 (8)	0.0730 (4)	−0.0615 (4)	0.0529 (16)
H5A	−0.1479	0.0296	−0.0889	0.063*
H5B	−0.2187	0.1102	−0.1065	0.063*
C6	−0.3173 (8)	0.0532 (4)	−0.0180 (5)	0.0609 (17)
H6A	−0.4058	0.0340	−0.0610	0.091*
H6B	−0.3514	0.0965	0.0091	0.091*
H6C	−0.2813	0.0161	0.0262	0.091*
C7	0.1748 (6)	−0.0157 (3)	0.3517 (4)	0.0343 (11)
C8	0.1567 (7)	−0.0772 (3)	0.2967 (4)	0.0441 (13)
H8	0.0916	−0.0748	0.2406	0.053*
C9	0.2357 (8)	−0.1410 (3)	0.3259 (5)	0.0554 (17)
H9	0.2249	−0.1823	0.2891	0.066*
C10	0.3301 (8)	−0.1454 (3)	0.4080 (5)	0.0573 (17)
H10	0.3822	−0.1897	0.4269	0.069*
C11	0.3491 (7)	−0.0861 (3)	0.4627 (4)	0.0487 (15)
H11	0.4138	−0.0893	0.5188	0.058*
C12	0.2714 (6)	−0.0208 (3)	0.4340 (4)	0.0393 (12)
H12	0.2846	0.0203	0.4710	0.047*
C13	0.1185 (6)	0.1331 (3)	0.3973 (4)	0.0373 (12)
C14	0.2545 (7)	0.1761 (3)	0.4030 (5)	0.0524 (16)
H14	0.3186	0.1711	0.3615	0.063*
C15	0.2949 (9)	0.2265 (3)	0.4705 (5)	0.064 (2)
H15	0.3868	0.2556	0.4749	0.077*
C16	0.2008 (11)	0.2338 (4)	0.5306 (5)	0.076 (2)
H16	0.2299	0.2674	0.5766	0.091*
C17	0.0651 (11)	0.1929 (4)	0.5246 (5)	0.072 (2)
H17	−0.0002	0.1997	0.5652	0.086*
C18	0.0245 (8)	0.1420 (4)	0.4592 (4)	0.0519 (15)
H18	−0.0671	0.1130	0.4561	0.062*
C19	−0.1353 (6)	0.0460 (3)	0.2935 (4)	0.0373 (12)
C20	−0.1923 (7)	−0.0064 (3)	0.3443 (4)	0.0475 (14)
H20	−0.1217	−0.0316	0.3884	0.057*
C21	−0.3544 (8)	−0.0206 (4)	0.3289 (5)	0.0600 (18)
H21	−0.3940	−0.0554	0.3634	0.072*
C22	−0.4584 (7)	0.0158 (4)	0.2634 (5)	0.0630 (19)
H22	−0.5679	0.0050	0.2529	0.076*
C23	−0.4032 (8)	0.0672 (5)	0.2141 (5)	0.070 (2)
H23	−0.4746	0.0927	0.1706	0.084*
C24	−0.2415 (7)	0.0817 (4)	0.2280 (5)	0.0528 (16)
H24	−0.2034	0.1162	0.1927	0.063*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Au	0.03006 (12)	0.03743 (13)	0.03915 (13)	−0.00125 (9)	0.00480 (8)	0.00592 (9)
S1	0.0394 (7)	0.0456 (8)	0.0407 (8)	−0.0062 (6)	0.0085 (6)	0.0044 (6)
P1	0.0251 (6)	0.0369 (7)	0.0361 (7)	−0.0021 (5)	0.0030 (5)	0.0027 (6)
O1	0.038 (2)	0.038 (2)	0.043 (2)	−0.0036 (16)	0.0052 (18)	−0.0004 (16)
N1	0.050 (3)	0.091 (4)	0.041 (3)	0.007 (3)	0.008 (3)	0.008 (3)
C1	0.037 (3)	0.040 (3)	0.050 (4)	0.002 (2)	0.009 (3)	0.005 (2)
C2	0.068 (5)	0.139 (8)	0.052 (5)	−0.002 (5)	0.019 (4)	0.006 (5)
C3	0.076 (6)	0.097 (7)	0.168 (11)	−0.030 (5)	0.016 (7)	0.058 (7)
C4	0.134 (9)	0.095 (7)	0.095 (8)	−0.037 (6)	0.026 (7)	0.003 (6)
C5	0.055 (4)	0.049 (4)	0.053 (4)	−0.007 (3)	0.006 (3)	−0.011 (3)
C6	0.049 (4)	0.064 (4)	0.067 (5)	−0.011 (3)	0.005 (3)	−0.010 (4)
C7	0.026 (3)	0.038 (3)	0.039 (3)	−0.004 (2)	0.007 (2)	0.003 (2)
C8	0.040 (3)	0.045 (3)	0.045 (4)	−0.004 (3)	0.005 (3)	−0.002 (3)
C9	0.054 (4)	0.036 (3)	0.076 (5)	−0.003 (3)	0.012 (4)	−0.005 (3)
C10	0.049 (4)	0.040 (3)	0.082 (5)	0.005 (3)	0.012 (4)	0.012 (3)
C11	0.037 (3)	0.050 (3)	0.053 (4)	0.000 (3)	−0.004 (3)	0.018 (3)
C12	0.037 (3)	0.040 (3)	0.038 (3)	0.001 (2)	0.002 (2)	0.006 (2)
C13	0.037 (3)	0.033 (3)	0.037 (3)	−0.001 (2)	−0.004 (2)	0.003 (2)
C14	0.041 (3)	0.036 (3)	0.074 (5)	−0.004 (3)	−0.003 (3)	0.003 (3)
C15	0.057 (4)	0.041 (3)	0.084 (6)	−0.012 (3)	−0.012 (4)	−0.001 (3)
C16	0.108 (7)	0.040 (4)	0.062 (5)	0.000 (4)	−0.021 (5)	−0.011 (3)
C17	0.100 (6)	0.066 (5)	0.052 (5)	−0.004 (4)	0.023 (4)	−0.011 (4)
C18	0.059 (4)	0.048 (3)	0.048 (4)	−0.002 (3)	0.012 (3)	0.002 (3)
C19	0.028 (3)	0.039 (3)	0.047 (3)	−0.003 (2)	0.014 (2)	−0.004 (2)
C20	0.032 (3)	0.064 (4)	0.046 (4)	−0.006 (3)	0.007 (3)	0.000 (3)
C21	0.044 (4)	0.084 (5)	0.056 (4)	−0.026 (3)	0.020 (3)	−0.011 (4)
C22	0.027 (3)	0.092 (5)	0.069 (5)	−0.014 (3)	0.008 (3)	−0.016 (4)
C23	0.032 (3)	0.098 (6)	0.075 (5)	0.005 (4)	0.003 (3)	0.005 (4)
C24	0.033 (3)	0.058 (4)	0.063 (5)	0.002 (3)	0.001 (3)	0.006 (3)

Geometric parameters (Å, º) top

Au—S1	2.2980 (14)	C9—C10	1.374 (10)
Au—P1	2.2561 (14)	C9—H9	0.9400
S1—C1	1.765 (7)	C10—C11	1.368 (9)
P1—C13	1.802 (6)	C10—H10	0.9400
P1—C19	1.803 (5)	C11—C12	1.390 (8)
P1—C7	1.811 (5)	C11—H11	0.9400
O1—C1	1.351 (7)	C12—H12	0.9400
O1—C5	1.458 (7)	C13—C14	1.392 (8)
N1—C1	1.262 (8)	C13—C18	1.395 (8)
N1—C2	1.479 (9)	C14—C15	1.390 (9)
C2—C3	1.397 (12)	C14—H14	0.9400
C2—H2A	0.9800	C15—C16	1.369 (11)
C2—H2B	0.9800	C15—H15	0.9400
C3—C4	1.550 (12)	C16—C17	1.369 (11)
C3—H3A	0.9800	C16—H16	0.9400
C3—H3B	0.9800	C17—C18	1.372 (9)
C4—H4A	0.9700	C17—H17	0.9400
C4—H4B	0.9700	C18—H18	0.9400
C4—H4C	0.9700	C19—C24	1.385 (8)
C5—C6	1.495 (9)	C19—C20	1.395 (8)
C5—H5A	0.9800	C20—C21	1.386 (8)
C5—H5B	0.9800	C20—H20	0.9400
C6—H6A	0.9700	C21—C22	1.383 (10)
C6—H6B	0.9700	C21—H21	0.9400
C6—H6C	0.9700	C22—C23	1.360 (10)
C7—C12	1.385 (7)	C22—H22	0.9400
C7—C8	1.402 (8)	C23—C24	1.385 (9)
C8—C9	1.375 (9)	C23—H23	0.9400
C8—H8	0.9400	C24—H24	0.9400

P1—Au—S1	176.66 (5)	C10—C9—C8	121.0 (6)
C1—S1—Au	102.8 (2)	C10—C9—H9	119.5
C13—P1—C19	107.4 (3)	C8—C9—H9	119.5
C13—P1—C7	105.1 (2)	C11—C10—C9	120.8 (6)
C19—P1—C7	104.6 (2)	C11—C10—H10	119.6
C13—P1—Au	112.22 (18)	C9—C10—H10	119.6
C19—P1—Au	112.84 (19)	C10—C11—C12	119.0 (6)
C7—P1—Au	114.06 (17)	C10—C11—H11	120.5
C1—O1—C5	116.0 (5)	C12—C11—H11	120.5
C1—N1—C2	119.6 (6)	C7—C12—C11	120.9 (5)
N1—C1—O1	121.1 (6)	C7—C12—H12	119.6
N1—C1—S1	127.1 (5)	C11—C12—H12	119.6
O1—C1—S1	111.9 (4)	C14—C13—C18	119.2 (6)
C3—C2—N1	114.0 (8)	C14—C13—P1	117.5 (5)
C3—C2—H2A	108.7	C18—C13—P1	123.3 (5)
N1—C2—H2A	108.7	C15—C14—C13	119.6 (7)
C3—C2—H2B	108.7	C15—C14—H14	120.2
N1—C2—H2B	108.7	C13—C14—H14	120.2
H2A—C2—H2B	107.6	C16—C15—C14	119.9 (7)
C2—C3—C4	111.5 (8)	C16—C15—H15	120.0
C2—C3—H3A	109.3	C14—C15—H15	120.0
C4—C3—H3A	109.3	C15—C16—C17	121.0 (7)
C2—C3—H3B	109.3	C15—C16—H16	119.5
C4—C3—H3B	109.3	C17—C16—H16	119.5
H3A—C3—H3B	108.0	C16—C17—C18	119.9 (7)
C3—C4—H4A	109.5	C16—C17—H17	120.1
C3—C4—H4B	109.5	C18—C17—H17	120.1
H4A—C4—H4B	109.5	C17—C18—C13	120.4 (6)
C3—C4—H4C	109.5	C17—C18—H18	119.8
H4A—C4—H4C	109.5	C13—C18—H18	119.8
H4B—C4—H4C	109.5	C24—C19—C20	119.3 (5)
O1—C5—C6	107.1 (5)	C24—C19—P1	118.7 (4)
O1—C5—H5A	110.3	C20—C19—P1	122.0 (5)
C6—C5—H5A	110.3	C21—C20—C19	119.2 (6)
O1—C5—H5B	110.3	C21—C20—H20	120.4
C6—C5—H5B	110.3	C19—C20—H20	120.4
H5A—C5—H5B	108.6	C22—C21—C20	120.6 (6)
C5—C6—H6A	109.5	C22—C21—H21	119.7
C5—C6—H6B	109.5	C20—C21—H21	119.7
H6A—C6—H6B	109.5	C23—C22—C21	120.3 (6)
C5—C6—H6C	109.5	C23—C22—H22	119.8
H6A—C6—H6C	109.5	C21—C22—H22	119.8
H6B—C6—H6C	109.5	C22—C23—C24	119.9 (7)
C12—C7—C8	119.2 (5)	C22—C23—H23	120.1
C12—C7—P1	123.3 (4)	C24—C23—H23	120.1
C8—C7—P1	117.4 (4)	C23—C24—C19	120.7 (6)
C9—C8—C7	119.0 (6)	C23—C24—H24	119.6
C9—C8—H8	120.5	C19—C24—H24	119.6
C7—C8—H8	120.5

P1—Au—S1—C1	159.5 (8)	C7—P1—C13—C14	89.8 (5)
S1—Au—P1—C13	57.7 (9)	Au—P1—C13—C14	−34.7 (5)
S1—Au—P1—C19	179 (100)	C19—P1—C13—C18	20.9 (6)
S1—Au—P1—C7	−61.8 (9)	C7—P1—C13—C18	−90.0 (5)
C2—N1—C1—O1	−176.8 (6)	Au—P1—C13—C18	145.5 (5)
C2—N1—C1—S1	4.1 (9)	C18—C13—C14—C15	0.6 (9)
C5—O1—C1—N1	2.2 (8)	P1—C13—C14—C15	−179.3 (5)
C5—O1—C1—S1	−178.6 (4)	C13—C14—C15—C16	−0.2 (10)
Au—S1—C1—N1	−163.6 (5)	C14—C15—C16—C17	−1.1 (11)
Au—S1—C1—O1	17.3 (4)	C15—C16—C17—C18	2.1 (12)
C1—N1—C2—C3	−118.2 (9)	C16—C17—C18—C13	−1.8 (11)
N1—C2—C3—C4	−174.3 (8)	C14—C13—C18—C17	0.4 (9)
C1—O1—C5—C6	178.9 (5)	P1—C13—C18—C17	−179.8 (5)
C13—P1—C7—C12	−3.5 (5)	C13—P1—C19—C24	98.2 (5)
C19—P1—C7—C12	−116.4 (5)	C7—P1—C19—C24	−150.5 (5)
Au—P1—C7—C12	119.9 (4)	Au—P1—C19—C24	−26.0 (5)
C13—P1—C7—C8	178.4 (4)	C13—P1—C19—C20	−82.7 (5)
C19—P1—C7—C8	65.5 (4)	C7—P1—C19—C20	28.6 (5)
Au—P1—C7—C8	−58.2 (4)	Au—P1—C19—C20	153.1 (4)
C12—C7—C8—C9	0.0 (8)	C24—C19—C20—C21	−1.0 (9)
P1—C7—C8—C9	178.1 (4)	P1—C19—C20—C21	180.0 (5)
C7—C8—C9—C10	0.6 (9)	C19—C20—C21—C22	0.8 (10)
C8—C9—C10—C11	−0.6 (10)	C20—C21—C22—C23	−1.2 (11)
C9—C10—C11—C12	0.0 (9)	C21—C22—C23—C24	1.7 (12)
C8—C7—C12—C11	−0.5 (8)	C22—C23—C24—C19	−1.8 (11)
P1—C7—C12—C11	−178.6 (4)	C20—C19—C24—C23	1.5 (10)
C10—C11—C12—C7	0.5 (8)	P1—C19—C24—C23	−179.4 (5)
C19—P1—C13—C14	−159.3 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8···N1ⁱ	0.94	2.54	3.433 (9)	159

Symmetry code: (i) −x, −y, −z.

Experimental details

Crystal data
Chemical formula	[Au(C₆H₁₂NOS)(C₁₈H₁₅P)]
M_r	605.46
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	223
a, b, c (Å)	8.5822 (6), 18.2036 (13), 15.6893 (12)
β (°)	102.001 (2)
V (Å³)	2397.5 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	6.30
Crystal size (mm)	0.16 × 0.05 × 0.04

Data collection
Diffractometer	Bruker SMART CCD diffractometer
Absorption correction	Multi-scan (SADABS, Bruker, 2000)
T_min, T_max	0.439, 1
No. of measured, independent and observed [I > 2σ(I)] reflections	16839, 5496, 4350
R_int	0.042
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.035, 0.098, 1.07
No. of reflections	5496
No. of parameters	262
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.19, −0.63

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 bond lengths (Å) top

Au—S1

2.2980 (14)

Au—P1

2.2561 (14)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8···N1ⁱ	0.94	2.54	3.433 (9)	159

Symmetry code: (i) −x, −y, −z.

Acknowledgements

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

References

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