[(Z)-O-Ethyl N-(4-chloro-phen-yl)thio-carbamato-κS](triphenyl-phosphine-κP)gold(I) dichloro-methane hemisolvate.

The Au(I) atom in the title compound, [Au(C(9)H(9)ClNOS)(C(18)H(15)P)]·0.5CH(2)Cl(2), exists within a slightly distorted linear geometry defined by an S,P donor set [S-Au-P angle = 178.01 (4)°]; a close intra-molecular Au⋯O contact [2.964 (4) Å] also occurs. In the crystal structure, mol-ecules are linked into supra-molecular chains propagating along [010] by C-H⋯N, C-H⋯S and C-H⋯π inter-actions. The solvent mol-ecule is disordered about a twofold rotation axis.

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(C9H9ClNOS)(C18H15P)]·0.5CH2Cl2

M = 716.40

Monoclinic,

a = 30.5163 (16) Å

b = 8.5881 (5) Å

c = 21.0518 (12) Å

β = 101.054 (1)°

V = 5414.8 (5) Å3

Z = 8

Mo Kα radiation

μ = 5.79 mm−1

T = 223 K

0.15 × 0.15 × 0.13 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T min = 0.672, T max = 1

18509 measured reflections

6214 independent reflections

5381 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.032

wR(F 2) = 0.092

S = 1.10

6214 reflections

306 parameters

H-atom parameters constrained

Δρmax = 1.73 e Å−3

Δρmin = −1.87 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: ORTEP-3 (Farrugia, 1997 ▶) and DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810018179/hb5453sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810018179/hb5453Isup2.hkl

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

[Au(C9H9ClNOS)(C18H15P)]·0.5CH2Cl2	F(000) = 2792
Mr = 716.40	Dx = 1.758 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71069 Å
Hall symbol: -C 2yc	Cell parameters from 6681 reflections
a = 30.5163 (16) Å	θ = 2.5–29.1°
b = 8.5881 (5) Å	µ = 5.79 mm−1
c = 21.0518 (12) Å	T = 223 K
β = 101.054 (1)°	Block, yellow
V = 5414.8 (5) Å3	0.15 × 0.15 × 0.13 mm
Z = 8

Bruker SMART CCD diffractometer	6214 independent reflections
Radiation source: fine-focus sealed tube	5381 reflections with I > 2σ(I)
graphite	Rint = 0.031
ω scans	θmax = 27.5°, θmin = 1.4°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −39→38
Tmin = 0.672, Tmax = 1	k = −6→11
18509 measured reflections	l = −27→27

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)] = 0.032	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.092	H-atom parameters constrained
S = 1.10	w = 1/[σ2(Fo2) + (0.05P)2 + 9.3001P] where P = (Fo2 + 2Fc2)/3
6214 reflections	(Δ/σ)max = 0.001
306 parameters	Δρmax = 1.73 e Å−3
0 restraints	Δρmin = −1.87 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	Occ. (<1)
Au	0.082143 (5)	0.03531 (2)	0.391240 (8)	0.02794 (7)
Cl1	−0.15255 (7)	0.6401 (2)	0.23755 (9)	0.0849 (7)
S1	0.01688 (4)	0.16692 (14)	0.35074 (6)	0.0351 (3)
P1	0.14730 (3)	−0.08554 (13)	0.43121 (5)	0.0251 (2)
O1	−0.00607 (11)	−0.0698 (4)	0.41402 (17)	0.0367 (8)
N1	−0.06288 (12)	0.1010 (5)	0.38198 (19)	0.0344 (9)
C1	−0.02287 (15)	0.0627 (5)	0.3836 (2)	0.0301 (9)
C2	−0.08159 (14)	0.2323 (6)	0.3475 (2)	0.0317 (9)
C3	−0.08667 (17)	0.2412 (7)	0.2804 (2)	0.0416 (11)
H3	−0.0754	0.1612	0.2577	0.050*
C4	−0.10818 (18)	0.3672 (7)	0.2469 (2)	0.0460 (13)
H4	−0.1114	0.3727	0.2017	0.055*
C5	−0.1248 (2)	0.4838 (7)	0.2801 (3)	0.0486 (14)
C6	−0.1206 (2)	0.4782 (7)	0.3461 (3)	0.0513 (15)
H6	−0.1321	0.5586	0.3684	0.062*
C7	−0.09900 (18)	0.3514 (7)	0.3793 (2)	0.0436 (12)
H7	−0.0962	0.3465	0.4245	0.052*
C8	−0.03693 (17)	−0.1648 (6)	0.4414 (3)	0.0438 (12)
H8A	−0.0639	−0.1860	0.4090	0.053*
H8B	−0.0456	−0.1117	0.4783	0.053*
C9	−0.0126 (2)	−0.3152 (7)	0.4631 (3)	0.0581 (16)
H9A	−0.0320	−0.3831	0.4821	0.087*
H9B	0.0141	−0.2922	0.4951	0.087*
H9C	−0.0042	−0.3663	0.4262	0.087*
C10	0.18807 (15)	−0.0764 (6)	0.3788 (2)	0.0291 (9)
C11	0.22367 (16)	−0.1789 (7)	0.3848 (2)	0.0387 (11)
H11	0.2262	−0.2602	0.4152	0.046*
C12	0.25552 (17)	−0.1628 (8)	0.3465 (3)	0.0494 (14)
H12	0.2799	−0.2317	0.3512	0.059*
C13	0.2511 (2)	−0.0445 (8)	0.3014 (3)	0.0568 (18)
H13	0.2727	−0.0324	0.2755	0.068*
C14	0.2155 (2)	0.0556 (8)	0.2940 (3)	0.0551 (16)
H14	0.2126	0.1346	0.2625	0.066*
C15	0.18380 (19)	0.0406 (6)	0.3324 (2)	0.0408 (12)
H15	0.1594	0.1094	0.3273	0.049*
C16	0.17531 (15)	−0.0050 (5)	0.5079 (2)	0.0270 (9)
C17	0.21857 (16)	0.0542 (6)	0.5187 (2)	0.0330 (10)
H17	0.2353	0.0500	0.4856	0.040*
C18	0.23708 (18)	0.1196 (7)	0.5781 (2)	0.0459 (13)
H18	0.2662	0.1603	0.5851	0.055*
C19	0.2125 (2)	0.1245 (6)	0.6267 (2)	0.0461 (13)
H19	0.2250	0.1692	0.6668	0.055*
C20	0.17016 (19)	0.0650 (7)	0.6171 (2)	0.0426 (12)
H20	0.1539	0.0677	0.6507	0.051*
C21	0.15130 (17)	0.0009 (6)	0.5579 (2)	0.0346 (10)
H21	0.1221	−0.0390	0.5514	0.042*
C22	0.13970 (14)	−0.2882 (5)	0.4482 (2)	0.0276 (9)
C23	0.16943 (15)	−0.3689 (6)	0.4943 (2)	0.0349 (10)
H23	0.1946	−0.3173	0.5178	0.042*
C24	0.16261 (19)	−0.5276 (6)	0.5068 (3)	0.0406 (12)
H24	0.1832	−0.5823	0.5377	0.049*
C25	0.12537 (18)	−0.6007 (6)	0.4730 (3)	0.0430 (12)
H25	0.1206	−0.7065	0.4809	0.052*
C26	0.0947 (2)	−0.5208 (7)	0.4275 (3)	0.0487 (14)
H26	0.0692	−0.5721	0.4050	0.058*
C27	0.10177 (16)	−0.3649 (6)	0.4152 (2)	0.0360 (10)
H27	0.0809	−0.3107	0.3845	0.043*
Cl2	0.5000	0.0930 (15)	0.2500	0.288 (5)*
Cl3	0.44248 (15)	0.3008 (6)	0.2579 (2)	0.0923 (12)*	0.50
C28	0.5000	0.2911 (17)	0.2500	0.101 (4)*
H28A	0.5054	0.3360	0.2094	0.122*	0.50
H28B	0.5205	0.3360	0.2870	0.122*	0.50

	U11	U22	U33	U12	U13	U23
Au	0.02219 (10)	0.02619 (11)	0.03374 (10)	0.00001 (6)	0.00111 (7)	0.00359 (7)
Cl1	0.0923 (13)	0.0844 (13)	0.0850 (12)	0.0519 (11)	0.0347 (10)	0.0537 (11)
S1	0.0244 (5)	0.0319 (6)	0.0480 (6)	0.0006 (5)	0.0041 (5)	0.0140 (5)
P1	0.0215 (5)	0.0231 (5)	0.0295 (5)	−0.0008 (4)	0.0022 (4)	0.0022 (4)
O1	0.0297 (17)	0.0335 (18)	0.0484 (19)	0.0048 (14)	0.0108 (14)	0.0135 (15)
N1	0.0287 (19)	0.037 (2)	0.040 (2)	0.0057 (17)	0.0116 (16)	0.0095 (18)
C1	0.029 (2)	0.031 (2)	0.030 (2)	0.0004 (18)	0.0043 (17)	0.0032 (18)
C2	0.022 (2)	0.037 (2)	0.037 (2)	0.0010 (19)	0.0071 (17)	0.011 (2)
C3	0.044 (3)	0.043 (3)	0.037 (2)	0.009 (2)	0.007 (2)	0.006 (2)
C4	0.047 (3)	0.055 (3)	0.034 (2)	0.003 (3)	0.004 (2)	0.010 (2)
C5	0.040 (3)	0.048 (3)	0.059 (3)	0.016 (2)	0.013 (3)	0.027 (3)
C6	0.060 (4)	0.043 (3)	0.056 (3)	0.020 (3)	0.024 (3)	0.008 (3)
C7	0.050 (3)	0.047 (3)	0.038 (2)	0.014 (3)	0.018 (2)	0.011 (2)
C8	0.035 (3)	0.041 (3)	0.058 (3)	0.003 (2)	0.016 (2)	0.021 (3)
C9	0.053 (3)	0.044 (3)	0.082 (4)	0.009 (3)	0.026 (3)	0.030 (3)
C10	0.029 (2)	0.032 (2)	0.0255 (19)	−0.0056 (19)	0.0037 (17)	−0.0043 (18)
C11	0.035 (2)	0.044 (3)	0.036 (2)	0.002 (2)	0.0049 (19)	−0.004 (2)
C12	0.032 (3)	0.075 (4)	0.043 (3)	−0.001 (3)	0.010 (2)	−0.017 (3)
C13	0.047 (3)	0.088 (5)	0.039 (3)	−0.023 (3)	0.021 (3)	−0.021 (3)
C14	0.069 (4)	0.062 (4)	0.037 (3)	−0.021 (3)	0.017 (3)	0.003 (3)
C15	0.045 (3)	0.040 (3)	0.037 (2)	−0.007 (2)	0.009 (2)	0.004 (2)
C16	0.026 (2)	0.023 (2)	0.031 (2)	0.0017 (17)	0.0029 (17)	0.0024 (17)
C17	0.026 (2)	0.035 (3)	0.037 (2)	−0.0047 (19)	0.0043 (18)	0.000 (2)
C18	0.040 (3)	0.047 (3)	0.046 (3)	−0.013 (3)	−0.005 (2)	−0.003 (3)
C19	0.064 (3)	0.039 (3)	0.032 (2)	−0.005 (3)	0.000 (2)	0.000 (2)
C20	0.052 (3)	0.044 (3)	0.033 (2)	−0.002 (2)	0.010 (2)	−0.002 (2)
C21	0.031 (2)	0.038 (3)	0.036 (2)	−0.001 (2)	0.0072 (19)	0.001 (2)
C22	0.028 (2)	0.022 (2)	0.034 (2)	−0.0022 (17)	0.0084 (17)	0.0012 (17)
C23	0.028 (2)	0.032 (3)	0.043 (2)	−0.0005 (19)	0.0030 (19)	0.004 (2)
C24	0.042 (3)	0.031 (3)	0.051 (3)	0.011 (2)	0.016 (2)	0.010 (2)
C25	0.056 (3)	0.023 (2)	0.055 (3)	−0.002 (2)	0.023 (3)	0.002 (2)
C26	0.054 (4)	0.035 (3)	0.058 (3)	−0.015 (3)	0.013 (3)	−0.009 (3)
C27	0.037 (2)	0.032 (3)	0.037 (2)	−0.006 (2)	0.001 (2)	0.000 (2)

Au—P1	2.2578 (11)	C12—H12	0.9400
Au—S1	2.3064 (11)	C13—C14	1.371 (10)
Cl1—C5	1.740 (5)	C13—H13	0.9400
S1—C1	1.753 (5)	C14—C15	1.381 (8)
P1—C22	1.801 (5)	C14—H14	0.9400
P1—C16	1.814 (5)	C15—H15	0.9400
P1—C10	1.816 (4)	C16—C17	1.392 (6)
O1—C1	1.358 (5)	C16—C21	1.394 (6)
O1—C8	1.447 (6)	C17—C18	1.387 (7)
N1—C1	1.259 (6)	C17—H17	0.9400
N1—C2	1.402 (6)	C18—C19	1.380 (8)
C2—C7	1.382 (7)	C18—H18	0.9400
C2—C3	1.393 (6)	C19—C20	1.368 (8)
C3—C4	1.386 (7)	C19—H19	0.9400
C3—H3	0.9400	C20—C21	1.382 (7)
C4—C5	1.372 (8)	C20—H20	0.9400
C4—H4	0.9400	C21—H21	0.9400
C5—C6	1.372 (9)	C22—C23	1.381 (6)
C6—C7	1.390 (7)	C22—C27	1.396 (6)
C6—H6	0.9400	C23—C24	1.411 (7)
C7—H7	0.9400	C23—H23	0.9400
C8—C9	1.516 (7)	C24—C25	1.372 (8)
C8—H8A	0.9800	C24—H24	0.9400
C8—H8B	0.9800	C25—C26	1.386 (9)
C9—H9A	0.9700	C25—H25	0.9400
C9—H9B	0.9700	C26—C27	1.388 (8)
C9—H9C	0.9700	C26—H26	0.9400
C10—C11	1.385 (7)	C27—H27	0.9400
C10—C15	1.389 (7)	Cl2—C28	1.701 (18)
C11—C12	1.383 (7)	Cl3—C28	1.797 (5)
C11—H11	0.9400	C28—H28A	0.9800
C12—C13	1.379 (9)	C28—H28B	0.9800
P1—Au—S1	178.01 (4)	C14—C13—C12	120.8 (5)
C1—S1—Au	102.58 (16)	C14—C13—H13	119.6
C22—P1—C16	104.4 (2)	C12—C13—H13	119.6
C22—P1—C10	107.0 (2)	C13—C14—C15	120.2 (6)
C16—P1—C10	105.3 (2)	C13—C14—H14	119.9
C22—P1—Au	112.37 (14)	C15—C14—H14	119.9
C16—P1—Au	112.79 (15)	C14—C15—C10	119.8 (5)
C10—P1—Au	114.24 (15)	C14—C15—H15	120.1
C1—O1—C8	116.4 (4)	C10—C15—H15	120.1
C1—N1—C2	121.4 (4)	C17—C16—C21	118.9 (4)
N1—C1—O1	120.5 (4)	C17—C16—P1	123.7 (4)
N1—C1—S1	126.7 (4)	C21—C16—P1	117.4 (3)
O1—C1—S1	112.8 (3)	C18—C17—C16	120.3 (5)
C7—C2—C3	118.1 (4)	C18—C17—H17	119.9
C7—C2—N1	120.1 (4)	C16—C17—H17	119.9
C3—C2—N1	121.6 (5)	C19—C18—C17	119.7 (5)
C4—C3—C2	120.6 (5)	C19—C18—H18	120.2
C4—C3—H3	119.7	C17—C18—H18	120.2
C2—C3—H3	119.7	C20—C19—C18	120.7 (5)
C5—C4—C3	119.8 (5)	C20—C19—H19	119.6
C5—C4—H4	120.1	C18—C19—H19	119.6
C3—C4—H4	120.1	C19—C20—C21	120.0 (5)
C6—C5—C4	121.2 (5)	C19—C20—H20	120.0
C6—C5—Cl1	119.3 (5)	C21—C20—H20	120.0
C4—C5—Cl1	119.5 (5)	C20—C21—C16	120.4 (5)
C5—C6—C7	118.6 (5)	C20—C21—H21	119.8
C5—C6—H6	120.7	C16—C21—H21	119.8
C7—C6—H6	120.7	C23—C22—C27	118.9 (4)
C2—C7—C6	121.8 (5)	C23—C22—P1	122.2 (3)
C2—C7—H7	119.1	C27—C22—P1	118.9 (3)
C6—C7—H7	119.1	C22—C23—C24	121.0 (4)
O1—C8—C9	106.3 (4)	C22—C23—H23	119.5
O1—C8—H8A	110.5	C24—C23—H23	119.5
C9—C8—H8A	110.5	C25—C24—C23	118.9 (5)
O1—C8—H8B	110.5	C25—C24—H24	120.5
C9—C8—H8B	110.5	C23—C24—H24	120.5
H8A—C8—H8B	108.7	C24—C25—C26	120.9 (5)
C8—C9—H9A	109.5	C24—C25—H25	119.5
C8—C9—H9B	109.5	C26—C25—H25	119.5
H9A—C9—H9B	109.5	C25—C26—C27	119.9 (5)
C8—C9—H9C	109.5	C25—C26—H26	120.1
H9A—C9—H9C	109.5	C27—C26—H26	120.1
H9B—C9—H9C	109.5	C26—C27—C22	120.4 (5)
C11—C10—C15	119.4 (4)	C26—C27—H27	119.8
C11—C10—P1	122.2 (4)	C22—C27—H27	119.8
C15—C10—P1	118.4 (4)	Cl2—C28—Cl3	92.7 (5)
C12—C11—C10	120.6 (5)	Cl2—C28—H28A	113.2
C12—C11—H11	119.7	Cl3—C28—H28A	113.2
C10—C11—H11	119.7	Cl2—C28—H28B	113.2
C11—C12—C13	119.2 (6)	Cl3—C28—H28B	113.2
C11—C12—H12	120.4	H28A—C28—H28B	110.5
C13—C12—H12	120.4
P1—Au—S1—C1	−143.5 (12)	C12—C13—C14—C15	1.0 (9)
S1—Au—P1—C22	171.4 (12)	C13—C14—C15—C10	−0.1 (9)
S1—Au—P1—C16	53.8 (12)	C11—C10—C15—C14	−1.4 (8)
S1—Au—P1—C10	−66.5 (12)	P1—C10—C15—C14	176.8 (4)
C2—N1—C1—O1	−176.1 (4)	C22—P1—C16—C17	114.7 (4)
C2—N1—C1—S1	5.2 (7)	C10—P1—C16—C17	2.2 (5)
C8—O1—C1—N1	2.4 (7)	Au—P1—C16—C17	−123.0 (4)
C8—O1—C1—S1	−178.8 (4)	C22—P1—C16—C21	−67.0 (4)
Au—S1—C1—N1	170.6 (4)	C10—P1—C16—C21	−179.5 (4)
Au—S1—C1—O1	−8.2 (4)	Au—P1—C16—C21	55.3 (4)
C1—N1—C2—C7	−121.0 (5)	C21—C16—C17—C18	−0.8 (7)
C1—N1—C2—C3	64.5 (7)	P1—C16—C17—C18	177.5 (4)
C7—C2—C3—C4	0.7 (8)	C16—C17—C18—C19	0.5 (8)
N1—C2—C3—C4	175.3 (5)	C17—C18—C19—C20	0.3 (9)
C2—C3—C4—C5	−0.3 (8)	C18—C19—C20—C21	−0.9 (9)
C3—C4—C5—C6	−0.1 (9)	C19—C20—C21—C16	0.6 (8)
C3—C4—C5—Cl1	−179.0 (5)	C17—C16—C21—C20	0.2 (7)
C4—C5—C6—C7	0.1 (10)	P1—C16—C21—C20	−178.1 (4)
Cl1—C5—C6—C7	178.9 (5)	C16—P1—C22—C23	−31.3 (4)
C3—C2—C7—C6	−0.7 (8)	C10—P1—C22—C23	80.0 (4)
N1—C2—C7—C6	−175.4 (5)	Au—P1—C22—C23	−153.9 (3)
C5—C6—C7—C2	0.4 (9)	C16—P1—C22—C27	146.6 (4)
C1—O1—C8—C9	171.6 (5)	C10—P1—C22—C27	−102.1 (4)
C22—P1—C10—C11	−35.4 (4)	Au—P1—C22—C27	24.0 (4)
C16—P1—C10—C11	75.3 (4)	C27—C22—C23—C24	1.9 (7)
Au—P1—C10—C11	−160.4 (3)	P1—C22—C23—C24	179.9 (4)
C22—P1—C10—C15	146.5 (4)	C22—C23—C24—C25	−1.1 (7)
C16—P1—C10—C15	−102.9 (4)	C23—C24—C25—C26	−0.2 (8)
Au—P1—C10—C15	21.4 (4)	C24—C25—C26—C27	0.6 (9)
C15—C10—C11—C12	1.9 (7)	C25—C26—C27—C22	0.3 (8)
P1—C10—C11—C12	−176.2 (4)	C23—C22—C27—C26	−1.5 (7)
C10—C11—C12—C13	−1.0 (8)	P1—C22—C27—C26	−179.5 (4)
C11—C12—C13—C14	−0.5 (9)

Cg1 is the centroid of the C22–C27 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C21—H21···N1i	0.94	2.55	3.310 (6)	138
C26—H26···S1ii	0.94	2.86	3.738 (6)	156
C7—H7···Cg1i	0.94	2.96	3.784 (5)	147

Table 1

Selected bond lengths (Å)

Au—P1	2.2578 (11)
Au—S1	2.3064 (11)

Table 2

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C22–C27 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C21—H21⋯N1i	0.94	2.55	3.310 (6)	138
C26—H26⋯S1ii	0.94	2.86	3.738 (6)	156
C7—H7⋯Cg1i	0.94	2.96	3.784 (5)	147

Symmetry codes: (i) ; (ii) .