[(Z)-O-Ethyl-N-(p-tol-yl)thio-carbamato-κS](triphenyl-phosphine)-κP]gold(I).

The title compound, [Au(C(10)H(12)NOS)(C(18)H(15)P)], features a linear S,P-donor set about the central Au atom. The thio-carbamate 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 = 653.50

Triclinic,

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[F 2 > 2σ(F 2)] = 0.025

wR(F 2) = 0.074

S = 1.04

5702 reflections

299 parameters

H-atom parameters constrained

Δρmax = 1.41 e Å−3

Δρmin = −0.98 e Å−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 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809047618/lh2951sup1.cif

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

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

[Au(C10H12NOS)(C18H15P)]	Z = 2
Mr = 653.50	F(000) = 640
Triclinic, P1	Dx = 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

Bruker SMART CCD diffractometer	5702 independent reflections
Radiation source: fine-focus sealed tube	5380 reflections with I > 2σ(I)
graphite	Rint = 0.019
ω scans	θmax = 27.5°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −11→11
Tmin = 0.311, Tmax = 1	k = −14→15
8852 measured reflections	l = −11→17

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(Fo2) + (0.0515P)2 + 0.0366P] where P = (Fo2 + 2Fc2)/3
5702 reflections	(Δ/σ)max = 0.001
299 parameters	Δρmax = 1.41 e Å−3
0 restraints	Δρmin = −0.98 e Å−3

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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)

Au—S1	2.2964 (9)
Au—P1	2.2601 (9)

P1—Au—S1

177.07 (3)