[(Z)-N-(3-Chloro-phen-yl)-O-ethyl-thio-carbamato-κS](triphenyl-phosphine-κP)gold(I).

The title compound, [Au(C(9)H(9)ClNOS)(C(18)H(15)P)], reveals a near linear geometry for the Au atom defined by a S,P-donor set [S-Au-P = 175.86 (3)°]. The deviation from linearity is ascribed to the proximate O atom derived from the thio-carbamato anion [Au⋯O = 2.967 (3) Å].

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 ▶).

Experimental

Crystal data

[Au(C9H9ClNOS)(C18H15P)]

M = 673.92

Triclinic,

a = 8.7561 (4) Å

b = 12.3514 (6) Å

c = 13.0432 (6) Å

α = 110.076 (1)°

β = 105.289 (1)°

γ = 97.481 (1)°

V = 1239.52 (10) Å3

Z = 2

Mo Kα radiation

μ = 6.21 mm−1

T = 223 K

0.11 × 0.10 × 0.05 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T min = 0.620, T max = 1

10396 measured reflections

5662 independent reflections

5184 reflections with I > 2σ(I)

R int = 0.022

Refinement

R[F 2 > 2σ(F 2)] = 0.027

wR(F 2) = 0.065

S = 1.03

5662 reflections

298 parameters

H-atom parameters constrained

Δρmax = 1.79 e Å−3

Δρmin = −0.51 e Å−3

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); data reduction: SHELXTL (Sheldrick, 2008 ▶); 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/S1600536809049551/ci2966sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809049551/ci2966Isup2.hkl

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

[Au(C9H9ClNOS)(C18H15P)]	Z = 2
Mr = 673.92	F(000) = 656
Triclinic, P1	Dx = 1.806 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71069 Å
a = 8.7561 (4) Å	Cell parameters from 5349 reflections
b = 12.3514 (6) Å	θ = 2.5–29.7°
c = 13.0432 (6) Å	µ = 6.21 mm−1
α = 110.076 (1)°	T = 223 K
β = 105.289 (1)°	Block, colourless
γ = 97.481 (1)°	0.11 × 0.10 × 0.05 mm
V = 1239.52 (10) Å3

Bruker SMART CCD area-detector diffractometer	5662 independent reflections
Radiation source: fine-focus sealed tube	5184 reflections with I > 2σ(I)
graphite	Rint = 0.022
ω scans	θmax = 27.5°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −11→11
Tmin = 0.620, Tmax = 1	k = −14→16
10396 measured reflections	l = −16→12

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)] = 0.027	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.065	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0376P)2] where P = (Fo2 + 2Fc2)/3
5662 reflections	(Δ/σ)max = 0.001
298 parameters	Δρmax = 1.79 e Å−3
0 restraints	Δρmin = −0.51 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	0.129193 (15)	0.238137 (11)	0.027706 (10)	0.02816 (5)
Cl	0.38116 (14)	0.55776 (11)	0.65290 (9)	0.0512 (3)
S1	0.15605 (12)	0.37252 (8)	0.20892 (7)	0.0345 (2)
P1	0.10947 (10)	0.09758 (8)	−0.14385 (7)	0.02494 (17)
O1	0.2140 (3)	0.4991 (2)	0.0947 (2)	0.0326 (5)
N1	0.1960 (4)	0.6110 (3)	0.2686 (3)	0.0331 (7)
C1	0.1923 (4)	0.5102 (3)	0.1967 (3)	0.0303 (7)
C2	0.1738 (4)	0.6210 (3)	0.3749 (3)	0.0312 (8)
C3	0.2780 (4)	0.5892 (3)	0.4543 (3)	0.0336 (8)
H3	0.3665	0.5596	0.4384	0.040*
C4	0.2509 (4)	0.6011 (3)	0.5561 (3)	0.0338 (8)
C5	0.1230 (5)	0.6436 (4)	0.5839 (3)	0.0409 (9)
H5	0.1046	0.6490	0.6530	0.049*
C6	0.0223 (5)	0.6783 (4)	0.5051 (4)	0.0459 (10)
H6	−0.0647	0.7093	0.5222	0.055*
C7	0.0478 (5)	0.6679 (4)	0.4030 (3)	0.0424 (9)
H7	−0.0209	0.6929	0.3516	0.051*
C8	0.2069 (5)	0.5990 (3)	0.0607 (3)	0.0362 (8)
H8A	0.2921	0.6694	0.1178	0.043*
H8B	0.1003	0.6180	0.0540	0.043*
C9	0.2333 (5)	0.5609 (4)	−0.0537 (4)	0.0406 (9)
H9A	0.2293	0.6245	−0.0812	0.061*
H9B	0.1486	0.4908	−0.1089	0.061*
H9C	0.3392	0.5426	−0.0454	0.061*
C10	−0.0985 (4)	0.0188 (3)	−0.2372 (3)	0.0262 (7)
C11	−0.1568 (4)	−0.1021 (3)	−0.2693 (3)	0.0308 (7)
H11	−0.0861	−0.1468	−0.2463	0.037*
C12	−0.3194 (4)	−0.1571 (4)	−0.3353 (3)	0.0379 (9)
H12	−0.3587	−0.2389	−0.3564	0.045*
C13	−0.4228 (4)	−0.0924 (4)	−0.3697 (3)	0.0416 (10)
H13	−0.5328	−0.1299	−0.4142	0.050*
C14	−0.3654 (5)	0.0279 (4)	−0.3389 (3)	0.0418 (9)
H14	−0.4366	0.0718	−0.3630	0.050*
C15	−0.2039 (4)	0.0843 (4)	−0.2728 (3)	0.0345 (8)
H15	−0.1654	0.1661	−0.2522	0.041*
C16	0.2160 (4)	−0.0128 (3)	−0.1206 (3)	0.0255 (7)
C17	0.3041 (5)	−0.0661 (3)	−0.1893 (3)	0.0373 (8)
H17	0.3025	−0.0508	−0.2553	0.045*
C18	0.3940 (5)	−0.1415 (4)	−0.1609 (4)	0.0429 (9)
H18	0.4555	−0.1759	−0.2068	0.051*
C19	0.3949 (4)	−0.1669 (3)	−0.0666 (3)	0.0374 (8)
H19	0.4568	−0.2183	−0.0478	0.045*
C20	0.3047 (5)	−0.1168 (4)	0.0007 (4)	0.0413 (9)
H20	0.3031	−0.1356	0.0645	0.050*
C21	0.2165 (4)	−0.0390 (3)	−0.0253 (3)	0.0360 (8)
H21	0.1568	−0.0038	0.0217	0.043*
C22	0.1982 (4)	0.1559 (3)	−0.2303 (3)	0.0270 (7)
C23	0.3065 (4)	0.2674 (3)	−0.1774 (3)	0.0306 (7)
H23	0.3297	0.3125	−0.0982	0.037*
C24	0.3804 (4)	0.3123 (3)	−0.2411 (3)	0.0354 (8)
H24	0.4528	0.3879	−0.2053	0.042*
C25	0.3477 (4)	0.2458 (4)	−0.3569 (3)	0.0369 (8)
H25	0.3989	0.2761	−0.3997	0.044*
C26	0.2395 (4)	0.1344 (4)	−0.4110 (3)	0.0341 (8)
H26	0.2177	0.0896	−0.4901	0.041*
C27	0.1640 (4)	0.0897 (3)	−0.3484 (3)	0.0320 (7)
H27	0.0897	0.0148	−0.3851	0.038*

	U11	U22	U33	U12	U13	U23
Au	0.03676 (8)	0.02413 (8)	0.02236 (8)	0.00739 (5)	0.01005 (5)	0.00752 (5)
Cl	0.0597 (6)	0.0573 (7)	0.0413 (6)	0.0284 (5)	0.0125 (5)	0.0232 (5)
S1	0.0550 (5)	0.0237 (4)	0.0238 (4)	0.0093 (4)	0.0137 (4)	0.0079 (3)
P1	0.0299 (4)	0.0239 (4)	0.0207 (4)	0.0058 (3)	0.0096 (3)	0.0079 (3)
O1	0.0441 (14)	0.0262 (13)	0.0291 (13)	0.0099 (10)	0.0136 (10)	0.0109 (10)
N1	0.0367 (15)	0.0286 (16)	0.0304 (16)	0.0084 (12)	0.0098 (12)	0.0081 (12)
C1	0.0289 (16)	0.0289 (18)	0.0291 (17)	0.0059 (13)	0.0054 (13)	0.0103 (14)
C2	0.0325 (17)	0.0243 (17)	0.0290 (17)	0.0047 (13)	0.0094 (14)	0.0027 (14)
C3	0.0323 (17)	0.0282 (18)	0.0333 (19)	0.0090 (14)	0.0080 (14)	0.0054 (14)
C4	0.0368 (18)	0.0289 (18)	0.0277 (18)	0.0087 (14)	0.0043 (14)	0.0065 (14)
C5	0.044 (2)	0.047 (2)	0.032 (2)	0.0134 (18)	0.0151 (16)	0.0127 (17)
C6	0.040 (2)	0.058 (3)	0.040 (2)	0.0272 (19)	0.0174 (17)	0.013 (2)
C7	0.043 (2)	0.046 (2)	0.035 (2)	0.0221 (18)	0.0096 (16)	0.0107 (17)
C8	0.0394 (19)	0.0261 (18)	0.042 (2)	0.0057 (15)	0.0076 (16)	0.0172 (16)
C9	0.051 (2)	0.036 (2)	0.043 (2)	0.0110 (17)	0.0185 (18)	0.0225 (17)
C10	0.0280 (15)	0.0312 (18)	0.0196 (15)	0.0065 (13)	0.0126 (12)	0.0070 (13)
C11	0.0346 (17)	0.0335 (19)	0.0272 (17)	0.0055 (14)	0.0125 (14)	0.0147 (14)
C12	0.0345 (18)	0.043 (2)	0.0333 (19)	−0.0013 (16)	0.0128 (15)	0.0140 (16)
C13	0.0273 (17)	0.063 (3)	0.032 (2)	0.0043 (17)	0.0120 (15)	0.0154 (19)
C14	0.0369 (19)	0.058 (3)	0.038 (2)	0.0227 (18)	0.0159 (16)	0.0200 (19)
C15	0.0400 (19)	0.037 (2)	0.0305 (18)	0.0159 (16)	0.0162 (15)	0.0121 (15)
C16	0.0260 (15)	0.0230 (16)	0.0228 (15)	0.0022 (12)	0.0054 (12)	0.0068 (12)
C17	0.051 (2)	0.037 (2)	0.036 (2)	0.0180 (17)	0.0224 (17)	0.0182 (16)
C18	0.043 (2)	0.042 (2)	0.053 (2)	0.0162 (17)	0.0254 (18)	0.0208 (19)
C19	0.0345 (18)	0.0284 (19)	0.047 (2)	0.0068 (15)	0.0077 (16)	0.0161 (16)
C20	0.050 (2)	0.043 (2)	0.040 (2)	0.0135 (18)	0.0150 (17)	0.0259 (18)
C21	0.0414 (19)	0.038 (2)	0.037 (2)	0.0134 (16)	0.0184 (16)	0.0199 (16)
C22	0.0298 (16)	0.0279 (17)	0.0276 (16)	0.0088 (13)	0.0120 (13)	0.0135 (13)
C23	0.0298 (16)	0.0311 (18)	0.0280 (17)	0.0040 (14)	0.0067 (13)	0.0117 (14)
C24	0.0300 (17)	0.033 (2)	0.044 (2)	0.0038 (14)	0.0097 (15)	0.0198 (16)
C25	0.0353 (18)	0.049 (2)	0.042 (2)	0.0157 (16)	0.0198 (16)	0.0291 (18)
C26	0.0352 (18)	0.045 (2)	0.0271 (18)	0.0139 (16)	0.0155 (14)	0.0152 (16)
C27	0.0335 (17)	0.0342 (19)	0.0305 (18)	0.0086 (14)	0.0129 (14)	0.0135 (15)

Au—P1	2.2588 (8)	C11—H11	0.94
Au—S1	2.3041 (9)	C12—C13	1.370 (6)
Cl—C4	1.745 (4)	C12—H12	0.94
S1—C1	1.759 (4)	C13—C14	1.383 (6)
P1—C22	1.807 (3)	C13—H13	0.94
P1—C16	1.813 (3)	C14—C15	1.384 (5)
P1—C10	1.817 (3)	C14—H14	0.94
O1—C1	1.356 (4)	C15—H15	0.94
O1—C8	1.451 (4)	C16—C17	1.386 (5)
N1—C1	1.265 (4)	C16—C21	1.387 (5)
N1—C2	1.416 (5)	C17—C18	1.378 (5)
C2—C7	1.386 (5)	C17—H17	0.94
C2—C3	1.392 (5)	C18—C19	1.368 (6)
C3—C4	1.372 (5)	C18—H18	0.94
C3—H3	0.94	C19—C20	1.377 (6)
C4—C5	1.377 (5)	C19—H19	0.94
C5—C6	1.392 (6)	C20—C21	1.384 (5)
C5—H5	0.94	C20—H20	0.94
C6—C7	1.375 (6)	C21—H21	0.94
C6—H6	0.94	C22—C23	1.391 (5)
C7—H7	0.94	C22—C27	1.400 (5)
C8—C9	1.494 (6)	C23—C24	1.387 (5)
C8—H8A	0.98	C23—H23	0.94
C8—H8B	0.98	C24—C25	1.377 (5)
C9—H9A	0.97	C24—H24	0.94
C9—H9B	0.97	C25—C26	1.389 (6)
C9—H9C	0.97	C25—H25	0.94
C10—C11	1.387 (5)	C26—C27	1.382 (5)
C10—C15	1.396 (5)	C26—H26	0.94
C11—C12	1.390 (5)	C27—H27	0.94
P1—Au—S1	175.86 (3)	C13—C12—C11	120.2 (4)
C1—S1—Au	103.15 (12)	C13—C12—H12	119.9
C22—P1—C16	106.60 (15)	C11—C12—H12	119.9
C22—P1—C10	104.86 (15)	C12—C13—C14	120.1 (4)
C16—P1—C10	107.11 (15)	C12—C13—H13	120.0
C22—P1—Au	113.34 (12)	C14—C13—H13	120.0
C16—P1—Au	110.08 (11)	C13—C14—C15	120.5 (4)
C10—P1—Au	114.33 (10)	C13—C14—H14	119.7
C1—O1—C8	117.8 (3)	C15—C14—H14	119.7
C1—N1—C2	119.6 (3)	C14—C15—C10	119.6 (4)
N1—C1—O1	120.3 (3)	C14—C15—H15	120.2
N1—C1—S1	127.7 (3)	C10—C15—H15	120.2
O1—C1—S1	111.9 (2)	C17—C16—C21	119.1 (3)
C7—C2—C3	118.6 (4)	C17—C16—P1	123.0 (3)
C7—C2—N1	119.2 (3)	C21—C16—P1	117.7 (3)
C3—C2—N1	122.2 (3)	C18—C17—C16	120.1 (4)
C4—C3—C2	119.6 (3)	C18—C17—H17	120.0
C4—C3—H3	120.2	C16—C17—H17	120.0
C2—C3—H3	120.2	C19—C18—C17	120.8 (4)
C3—C4—C5	122.6 (3)	C19—C18—H18	119.6
C3—C4—Cl	118.6 (3)	C17—C18—H18	119.6
C5—C4—Cl	118.7 (3)	C18—C19—C20	119.7 (4)
C4—C5—C6	117.2 (4)	C18—C19—H19	120.1
C4—C5—H5	121.4	C20—C19—H19	120.1
C6—C5—H5	121.4	C19—C20—C21	120.2 (4)
C7—C6—C5	121.2 (4)	C19—C20—H20	119.9
C7—C6—H6	119.4	C21—C20—H20	119.9
C5—C6—H6	119.4	C20—C21—C16	120.1 (3)
C6—C7—C2	120.7 (4)	C20—C21—H21	119.9
C6—C7—H7	119.6	C16—C21—H21	119.9
C2—C7—H7	119.6	C23—C22—C27	119.4 (3)
O1—C8—C9	105.7 (3)	C23—C22—P1	119.2 (3)
O1—C8—H8A	110.6	C27—C22—P1	121.4 (3)
C9—C8—H8A	110.6	C24—C23—C22	120.2 (3)
O1—C8—H8B	110.6	C24—C23—H23	119.9
C9—C8—H8B	110.6	C22—C23—H23	119.9
H8A—C8—H8B	108.7	C25—C24—C23	120.0 (3)
C8—C9—H9A	109.5	C25—C24—H24	120.0
C8—C9—H9B	109.5	C23—C24—H24	120.0
H9A—C9—H9B	109.5	C24—C25—C26	120.5 (3)
C8—C9—H9C	109.5	C24—C25—H25	119.8
H9A—C9—H9C	109.5	C26—C25—H25	119.8
H9B—C9—H9C	109.5	C27—C26—C25	119.9 (3)
C11—C10—C15	119.5 (3)	C27—C26—H26	120.0
C11—C10—P1	122.3 (3)	C25—C26—H26	120.0
C15—C10—P1	118.2 (3)	C26—C27—C22	120.0 (3)
C10—C11—C12	120.2 (4)	C26—C27—H27	120.0
C10—C11—H11	119.9	C22—C27—H27	120.0
C12—C11—H11	119.9
C2—N1—C1—O1	−179.7 (3)	C11—C10—C15—C14	0.6 (5)
C2—N1—C1—S1	2.0 (5)	P1—C10—C15—C14	−176.6 (3)
C8—O1—C1—N1	−12.7 (5)	C22—P1—C16—C17	−19.4 (3)
C8—O1—C1—S1	165.9 (2)	C10—P1—C16—C17	92.4 (3)
Au—S1—C1—N1	170.7 (3)	Au—P1—C16—C17	−142.7 (3)
Au—S1—C1—O1	−7.7 (2)	C22—P1—C16—C21	156.6 (3)
C1—N1—C2—C7	−122.2 (4)	C10—P1—C16—C21	−91.6 (3)
C1—N1—C2—C3	60.1 (5)	Au—P1—C16—C21	33.3 (3)
C7—C2—C3—C4	2.1 (5)	C21—C16—C17—C18	−1.7 (5)
N1—C2—C3—C4	179.8 (3)	P1—C16—C17—C18	174.3 (3)
C2—C3—C4—C5	0.2 (6)	C16—C17—C18—C19	1.4 (6)
C2—C3—C4—Cl	178.8 (3)	C17—C18—C19—C20	0.1 (6)
C3—C4—C5—C6	−1.9 (6)	C18—C19—C20—C21	−1.5 (6)
Cl—C4—C5—C6	179.5 (3)	C19—C20—C21—C16	1.3 (6)
C4—C5—C6—C7	1.4 (7)	C17—C16—C21—C20	0.3 (5)
C5—C6—C7—C2	0.8 (7)	P1—C16—C21—C20	−175.8 (3)
C3—C2—C7—C6	−2.6 (6)	C16—P1—C22—C23	−103.6 (3)
N1—C2—C7—C6	179.6 (4)	C10—P1—C22—C23	143.0 (3)
C1—O1—C8—C9	−179.6 (3)	Au—P1—C22—C23	17.6 (3)
C22—P1—C10—C11	119.2 (3)	C16—P1—C22—C27	74.4 (3)
C16—P1—C10—C11	6.1 (3)	C10—P1—C22—C27	−39.0 (3)
Au—P1—C10—C11	−116.1 (3)	Au—P1—C22—C27	−164.4 (2)
C22—P1—C10—C15	−63.8 (3)	C27—C22—C23—C24	−0.3 (5)
C16—P1—C10—C15	−176.8 (3)	P1—C22—C23—C24	177.8 (3)
Au—P1—C10—C15	61.0 (3)	C22—C23—C24—C25	−0.6 (5)
C15—C10—C11—C12	−0.8 (5)	C23—C24—C25—C26	0.7 (6)
P1—C10—C11—C12	176.3 (3)	C24—C25—C26—C27	0.0 (6)
C10—C11—C12—C13	0.4 (5)	C25—C26—C27—C22	−0.8 (5)
C11—C12—C13—C14	0.1 (6)	C23—C22—C27—C26	1.0 (5)
C12—C13—C14—C15	−0.3 (6)	P1—C22—C27—C26	−177.0 (3)
C13—C14—C15—C10	0.0 (6)