[O-Methyl N-(4-chloro­phen­yl)thio­carbamato-κS]­(triethyl­phosphine-κP)gold(I)

The mol­ecules of the title complex, Et₃PAu[SC(OMe)=N(C₆H₄Cl-4)] or [Au(C₈H₇ClNOS)(C₆H₁₅P)], involve the Au atom with linear coordination [Au—P = 2.2584 (10) Å, Au—S = 2.3156 (10)Å and P—Au—S = 178.32 (4)°] and are linked into centrosymmetric dimers via secondary Au...S inter­actions [3.7616 (11) Å].

Key indicators

• Single-crystal X-ray study
• T = 223 K
• Mean [sigma](C-C)= 0.006 Å
• R factor = 0.036
• wR factor = 0.089
• Data-to-parameter ratio = 28.9

checkCIF/PLATON results

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Computing details

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, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.

[O-Methyl N-(4-chlorophenyl)thiocarbamato-κS](triethylphosphine-κP)gold(I)

Crystal data

[Au(C8H7ClNOS)(C6H15P)]	Dx = 1.901 Mg m^−3
Mr = 515.77	Mo Kα radiation, λ = 0.71069 Å
Tetragonal, P4/n	Cell parameters from 6061 reflections
Hall symbol: -P 4a	θ = 2.6–28.0°
a = 21.5192 (9) Å	µ = 8.51 mm^−1
c = 7.7834 (5) Å	T = 223 K
V = 3604.3 (3) Å^3	Needle, colourless
Z = 8	0.32 × 0.06 × 0.03 mm
F(000) = 1984

Data collection

Bruker SMART CCD diffractometer	5255 independent reflections
Radiation source: fine-focus sealed tube	3864 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.067
ω scans	θmax = 30.0°, θmin = 1.3°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −30→29
Tmin = 0.185, Tmax = 0.775	k = −30→22
29353 measured reflections	l = −9→10

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.089	H-atom parameters constrained
S = 1.01	w = 1/[σ^2(Fo^2) + (0.0432P)^2 + 0.245P] where P = (Fo^2 + 2Fc^2)/3
5255 reflections	(Δ/σ)max = 0.001
182 parameters	Δρmax = 1.68 e Å^−3
0 restraints	Δρmin = −0.87 e Å^−3

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'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 > σ(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 (Ų)

	x	y	z	Uiso*/Ueq
Au	0.059321 (8)	0.434377 (8)	0.06604 (2)	0.04180 (7)
Cl1	0.19082 (6)	0.68489 (6)	−0.81205 (15)	0.0596 (3)
S1	0.09847 (5)	0.49690 (5)	−0.15054 (14)	0.0449 (2)
P1	0.02376 (5)	0.37179 (5)	0.27720 (13)	0.0395 (2)
O1	0.17940 (16)	0.40732 (15)	−0.1155 (4)	0.0559 (8)
N1	0.19928 (19)	0.46963 (18)	−0.3441 (5)	0.0509 (9)
C1	0.1649 (2)	0.4573 (2)	−0.2169 (5)	0.0441 (9)
C2	0.1884 (2)	0.5226 (2)	−0.4460 (5)	0.0421 (9)
C3	0.2067 (2)	0.5811 (2)	−0.3900 (6)	0.0459 (10)
H3	0.2202	0.5865	−0.2761	0.055*
C4	0.2052 (2)	0.6317 (2)	−0.5008 (6)	0.0439 (9)
H4	0.2177	0.6712	−0.4624	0.053*
C5	0.1853 (2)	0.6234 (2)	−0.6670 (5)	0.0427 (9)
C6	0.1648 (2)	0.5671 (2)	−0.7234 (6)	0.0439 (9)
H6	0.1494	0.5625	−0.8357	0.053*
C7	0.1668 (2)	0.5164 (2)	−0.6125 (6)	0.0471 (10)
H7	0.1533	0.4773	−0.6514	0.057*
C8	0.2357 (3)	0.3747 (3)	−0.1608 (8)	0.0705 (16)
H8A	0.2327	0.3600	−0.2784	0.106*
H8B	0.2412	0.3395	−0.0843	0.106*
H8C	0.2709	0.4025	−0.1502	0.106*
C9	0.0783 (2)	0.3096 (2)	0.3243 (6)	0.0485 (10)
H9A	0.0630	0.2861	0.4236	0.058*
H9B	0.0797	0.2812	0.2261	0.058*
C10	0.1434 (3)	0.3319 (3)	0.3621 (10)	0.0835 (19)
H10A	0.1700	0.2965	0.3847	0.125*
H10B	0.1428	0.3589	0.4619	0.125*
H10C	0.1592	0.3547	0.2639	0.125*
C11	0.0091 (3)	0.4127 (2)	0.4763 (6)	0.0520 (11)
H11A	0.0470	0.4350	0.5087	0.062*
H11B	−0.0232	0.4439	0.4551	0.062*
C12	−0.0113 (3)	0.3726 (2)	0.6294 (6)	0.0597 (13)
H12A	−0.0179	0.3989	0.7290	0.090*
H12B	0.0207	0.3423	0.6548	0.090*
H12C	−0.0497	0.3513	0.6012	0.090*
C13	−0.0479 (2)	0.3319 (2)	0.2263 (6)	0.0476 (10)
H13A	−0.0571	0.3019	0.3177	0.057*
H13B	−0.0819	0.3622	0.2230	0.057*
C14	−0.0454 (3)	0.2977 (3)	0.0550 (6)	0.0700 (17)
H14A	−0.0850	0.2776	0.0338	0.105*
H14B	−0.0128	0.2666	0.0586	0.105*
H14C	−0.0368	0.3271	−0.0364	0.105*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Au	0.04424 (11)	0.04421 (11)	0.03694 (10)	−0.00807 (6)	0.00200 (6)	0.00741 (6)
Cl1	0.0736 (8)	0.0527 (7)	0.0524 (7)	0.0082 (6)	0.0066 (6)	0.0137 (5)
S1	0.0456 (6)	0.0471 (6)	0.0419 (5)	−0.0005 (4)	0.0062 (4)	0.0113 (5)
P1	0.0422 (6)	0.0381 (6)	0.0382 (5)	−0.0042 (4)	0.0018 (4)	0.0062 (4)
O1	0.059 (2)	0.0457 (19)	0.063 (2)	0.0047 (15)	0.0115 (16)	0.0201 (15)
N1	0.054 (2)	0.048 (2)	0.051 (2)	0.0057 (17)	0.0128 (18)	0.0117 (18)
C1	0.050 (3)	0.042 (2)	0.041 (2)	−0.0053 (18)	0.0030 (18)	0.0042 (18)
C2	0.036 (2)	0.043 (2)	0.047 (2)	0.0013 (16)	0.0114 (17)	0.0076 (18)
C3	0.050 (3)	0.049 (3)	0.039 (2)	0.0001 (19)	0.0024 (18)	0.0008 (18)
C4	0.045 (2)	0.039 (2)	0.048 (2)	−0.0041 (17)	0.000 (2)	−0.0018 (19)
C5	0.038 (2)	0.045 (2)	0.045 (2)	0.0044 (17)	0.0007 (18)	0.0068 (18)
C6	0.040 (2)	0.050 (3)	0.042 (2)	−0.0004 (18)	−0.0043 (18)	0.0015 (19)
C7	0.044 (2)	0.042 (2)	0.055 (3)	−0.0077 (18)	0.000 (2)	−0.001 (2)
C8	0.067 (4)	0.059 (3)	0.085 (4)	0.020 (3)	0.008 (3)	0.017 (3)
C9	0.046 (3)	0.043 (2)	0.056 (3)	−0.0031 (18)	−0.002 (2)	0.002 (2)
C10	0.055 (3)	0.063 (4)	0.132 (6)	−0.002 (3)	−0.024 (4)	0.016 (4)
C11	0.074 (3)	0.041 (2)	0.040 (2)	−0.003 (2)	−0.001 (2)	0.0039 (19)
C12	0.080 (4)	0.060 (3)	0.039 (2)	−0.004 (3)	0.012 (2)	0.002 (2)
C13	0.046 (2)	0.047 (3)	0.050 (2)	−0.0093 (19)	−0.0010 (19)	0.010 (2)
C14	0.083 (4)	0.086 (4)	0.041 (3)	−0.033 (3)	−0.014 (2)	0.009 (2)

Geometric parameters (Å, º)

Au—S1	2.3156 (10)	C8—H8A	0.9700
Au—P1	2.2584 (10)	C8—H8B	0.9700
Cl1—C5	1.743 (4)	C8—H8C	0.9700
S1—C1	1.742 (5)	C9—C10	1.510 (7)
P1—C11	1.810 (5)	C9—H9A	0.9800
P1—C13	1.810 (4)	C9—H9B	0.9800
P1—C9	1.817 (5)	C10—H10A	0.9700
O1—C1	1.370 (5)	C10—H10B	0.9700
O1—C8	1.444 (6)	C10—H10C	0.9700
N1—C1	1.264 (5)	C11—C12	1.536 (6)
N1—C2	1.409 (5)	C11—H11A	0.9800
C2—C7	1.383 (6)	C11—H11B	0.9800
C2—C3	1.389 (6)	C12—H12A	0.9700
C3—C4	1.389 (6)	C12—H12B	0.9700
C3—H3	0.9400	C12—H12C	0.9700
C4—C5	1.374 (6)	C13—C14	1.524 (7)
C4—H4	0.9400	C13—H13A	0.9800
C5—C6	1.364 (6)	C13—H13B	0.9800
C6—C7	1.391 (6)	C14—H14A	0.9700
C6—H6	0.9400	C14—H14B	0.9700
C7—H7	0.9400	C14—H14C	0.9700
S1—Au—P1	178.32 (4)	C10—C9—P1	113.8 (3)
Au—S1—C1	103.31 (15)	C10—C9—H9A	108.8
C11—P1—C13	105.6 (2)	P1—C9—H9A	108.8
C11—P1—C9	107.4 (2)	C10—C9—H9B	108.8
C13—P1—C9	104.2 (2)	P1—C9—H9B	108.8
C11—P1—Au	113.07 (16)	H9A—C9—H9B	107.7
C13—P1—Au	114.37 (15)	C9—C10—H10A	109.5
C9—P1—Au	111.55 (16)	C9—C10—H10B	109.5
C1—O1—C8	115.6 (4)	H10A—C10—H10B	109.5
C1—N1—C2	120.9 (4)	C9—C10—H10C	109.5
N1—C1—O1	118.8 (4)	H10A—C10—H10C	109.5
N1—C1—S1	127.6 (4)	H10B—C10—H10C	109.5
O1—C1—S1	113.6 (3)	C12—C11—P1	116.1 (4)
N1—C2—C7	120.3 (4)	C12—C11—H11A	108.3
N1—C2—C3	120.6 (4)	P1—C11—H11A	108.3
C7—C2—C3	118.5 (4)	C12—C11—H11B	108.3
C4—C3—C2	120.6 (4)	P1—C11—H11B	108.3
C4—C3—H3	119.7	H11A—C11—H11B	107.4
C2—C3—H3	119.7	C11—C12—H12A	109.5
C5—C4—C3	119.3 (4)	C11—C12—H12B	109.5
C5—C4—H4	120.3	H12A—C12—H12B	109.5
C3—C4—H4	120.3	C11—C12—H12C	109.5
C6—C5—C4	121.3 (4)	H12A—C12—H12C	109.5
C6—C5—Cl1	119.2 (3)	H12B—C12—H12C	109.5
C4—C5—Cl1	119.4 (3)	C14—C13—P1	113.0 (3)
C5—C6—C7	119.2 (4)	C14—C13—H13A	109.0
C5—C6—H6	120.4	P1—C13—H13A	109.0
C7—C6—H6	120.4	C14—C13—H13B	109.0
C6—C7—C2	121.0 (4)	P1—C13—H13B	109.0
C6—C7—H7	119.5	H13A—C13—H13B	107.8
C2—C7—H7	119.5	C13—C14—H14A	109.5
O1—C8—H8A	109.5	C13—C14—H14B	109.5
O1—C8—H8B	109.5	H14A—C14—H14B	109.5
H8A—C8—H8B	109.5	C13—C14—H14C	109.5
O1—C8—H8C	109.5	H14A—C14—H14C	109.5
H8A—C8—H8C	109.5	H14B—C14—H14C	109.5
H8B—C8—H8C	109.5
C2—N1—C1—O1	−176.2 (4)	Cl1—C5—C6—C7	173.0 (3)
C2—N1—C1—S1	4.0 (7)	C5—C6—C7—C2	1.1 (7)
C8—O1—C1—N1	2.9 (7)	N1—C2—C7—C6	−170.2 (4)
C8—O1—C1—S1	−177.3 (4)	C3—C2—C7—C6	1.5 (7)
Au—S1—C1—N1	172.5 (4)	C11—P1—C9—C10	−71.3 (5)
Au—S1—C1—O1	−7.3 (4)	C13—P1—C9—C10	177.0 (4)
C1—N1—C2—C7	−110.4 (5)	Au—P1—C9—C10	53.1 (5)
C1—N1—C2—C3	78.2 (6)	C13—P1—C11—C12	57.9 (4)
N1—C2—C3—C4	169.6 (4)	C9—P1—C11—C12	−52.8 (4)
C7—C2—C3—C4	−2.0 (7)	Au—P1—C11—C12	−176.3 (3)
C2—C3—C4—C5	0.0 (7)	C11—P1—C13—C14	176.5 (4)
C3—C4—C5—C6	2.6 (7)	C9—P1—C13—C14	−70.5 (4)
C3—C4—C5—Cl1	−173.6 (3)	Au—P1—C13—C14	51.5 (4)
C4—C5—C6—C7	−3.2 (7)