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

The Au atom in the title compound, [Au(C(8)H(7)ClNOS)(C(18)H(15)P)], exists within a slightly distorted linear geometry defined by an S,P-donor set [S-Au-P angle = 174.61 (4)°], with the distortion related to a short intra-molecular Au⋯O contact [2.988 (3) Å]. In the crystal structure, mol-ecules are arranged into supra-molecular chains along the b axis by C-H⋯π inter-actions.

Related literature

For the structural systematics and luminescence properties of <span class="Chemical">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

[<span class="Chemical">Au(C8H7ClNOS)(<span class="Chemical">C18H15P)]

M = 659.89

Triclinic,

a = 10.4236 (8) Å

b = 10.6961 (8) Å

c = 12.7439 (9) Å

α = 72.724 (2)°

β = 66.105 (1)°

γ = 72.530 (2)°

V = 1213.83 (16) Å3

Z = 2

Mo Kα radiation

μ = 6.34 mm−1

T = 223 K

0.19 × 0.08 × 0.05 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T min = 0.515, T max = 1

8630 measured reflections

5525 independent reflections

4787 reflections with I > 2σ(I)

R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.032

wR(F 2) = 0.089

S = 1.05

5525 reflections

290 parameters

H-atom parameters constrained

Δρmax = 1.16 e Å−3

Δρmin = −1.21 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 <span class="Disease">DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810017319/lh5042sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810017319/lh5042Isup2.hkl

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

[Au(C8H7ClNOS)(C18H15P)]	Z = 2
Mr = 659.89	F(000) = 640
Triclinic, P1	Dx = 1.805 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71069 Å
a = 10.4236 (8) Å	Cell parameters from 6911 reflections
b = 10.6961 (8) Å	θ = 1.8–30.1°
c = 12.7439 (9) Å	µ = 6.34 mm−1
α = 72.724 (2)°	T = 223 K
β = 66.105 (1)°	Block, colourless
γ = 72.530 (2)°	0.19 × 0.08 × 0.05 mm
V = 1213.83 (16) Å3

Bruker SMART CCD diffractometer	5525 independent reflections
Radiation source: fine-focus sealed tube	4787 reflections with I > 2σ(I)
graphite	Rint = 0.023
ω scans	θmax = 27.5°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −11→13
Tmin = 0.515, Tmax = 1	k = −13→13
8630 measured reflections	l = −15→16

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) = 0.089	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0473P)2] where P = (Fo2 + 2Fc2)/3
5525 reflections	(Δ/σ)max < 0.001
290 parameters	Δρmax = 1.16 e Å−3
0 restraints	Δρmin = −1.21 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	0.11162 (2)	0.105503 (16)	0.249566 (14)	0.03318 (8)
Cl1	0.29679 (17)	−0.34461 (14)	−0.25655 (13)	0.0480 (3)
S1	0.1802 (2)	−0.03071 (14)	0.11917 (12)	0.0569 (5)
P1	0.05527 (13)	0.25261 (11)	0.36314 (10)	0.0234 (2)
O1	0.2184 (4)	0.2044 (3)	−0.0097 (3)	0.0418 (9)
N1	0.3288 (5)	0.0379 (4)	−0.1105 (3)	0.0349 (9)
C1	0.2538 (6)	0.0735 (5)	−0.0159 (4)	0.0341 (11)
C2	0.3735 (5)	−0.0998 (5)	−0.1156 (4)	0.0316 (10)
C3	0.3166 (5)	−0.1501 (5)	−0.1734 (4)	0.0314 (10)
H3	0.2451	−0.0950	−0.2035	0.038*
C4	0.3677 (5)	−0.2828 (5)	−0.1855 (4)	0.0317 (10)
C5	0.4734 (6)	−0.3662 (5)	−0.1412 (4)	0.0371 (12)
H5	0.5049	−0.4566	−0.1474	0.045*
C6	0.5304 (6)	−0.3132 (6)	−0.0882 (5)	0.0409 (12)
H6	0.6033	−0.3676	−0.0594	0.049*
C7	0.4820 (6)	−0.1809 (5)	−0.0766 (4)	0.0363 (11)
H7	0.5239	−0.1460	−0.0416	0.044*
C8	0.2819 (8)	0.2932 (5)	−0.1111 (5)	0.0521 (15)
H8A	0.3855	0.2663	−0.1339	0.078*
H8B	0.2515	0.3829	−0.0956	0.078*
H8C	0.2528	0.2917	−0.1739	0.078*
C9	0.0939 (5)	0.4105 (4)	0.2678 (4)	0.0234 (9)
C10	0.0614 (5)	0.4495 (5)	0.1642 (4)	0.0304 (10)
H10	0.0210	0.3945	0.1462	0.037*
C11	0.0890 (6)	0.5678 (5)	0.0901 (5)	0.0399 (12)
H11	0.0651	0.5949	0.0219	0.048*
C12	0.1513 (6)	0.6478 (5)	0.1140 (4)	0.0343 (11)
H12	0.1703	0.7286	0.0618	0.041*
C13	0.1852 (5)	0.6108 (5)	0.2118 (5)	0.0371 (12)
H13	0.2286	0.6656	0.2271	0.044*
C14	0.1562 (5)	0.4911 (4)	0.2909 (4)	0.0282 (10)
H14	0.1791	0.4661	0.3594	0.034*
C15	−0.1311 (5)	0.2901 (5)	0.4571 (4)	0.0275 (10)
C16	−0.2001 (6)	0.1849 (6)	0.5219 (5)	0.0405 (12)
H16	−0.1521	0.0965	0.5143	0.049*
C17	−0.3406 (6)	0.2107 (7)	0.5980 (5)	0.0540 (17)
H17	−0.3868	0.1393	0.6437	0.065*
C18	−0.4121 (6)	0.3393 (7)	0.6068 (5)	0.0527 (16)
H18	−0.5081	0.3558	0.6569	0.063*
C19	−0.3451 (6)	0.4442 (6)	0.5434 (5)	0.0435 (13)
H19	−0.3942	0.5322	0.5512	0.052*
C20	−0.2039 (5)	0.4195 (5)	0.4673 (4)	0.0334 (11)
H20	−0.1580	0.4913	0.4227	0.040*
C21	0.1557 (5)	0.2115 (4)	0.4603 (4)	0.0239 (9)
C22	0.3060 (5)	0.1834 (5)	0.4125 (4)	0.0351 (11)
H22	0.3522	0.1829	0.3321	0.042*
C23	0.3858 (6)	0.1567 (5)	0.4825 (5)	0.0407 (12)
H23	0.4864	0.1408	0.4497	0.049*
C24	0.3169 (6)	0.1532 (5)	0.6035 (5)	0.0387 (12)
H24	0.3716	0.1345	0.6517	0.046*
C25	0.1711 (6)	0.1769 (6)	0.6509 (4)	0.0398 (12)
H25	0.1257	0.1725	0.7320	0.048*
C26	0.0902 (5)	0.2070 (5)	0.5816 (4)	0.0340 (11)
H26	−0.0104	0.2250	0.6153	0.041*

	U11	U22	U33	U12	U13	U23
Au	0.05238 (14)	0.02569 (11)	0.02024 (10)	−0.01321 (8)	−0.00694 (8)	−0.00573 (7)
Cl1	0.0597 (9)	0.0487 (8)	0.0462 (8)	−0.0174 (7)	−0.0213 (7)	−0.0137 (6)
S1	0.1055 (13)	0.0342 (7)	0.0234 (6)	−0.0339 (8)	0.0019 (7)	−0.0102 (5)
P1	0.0305 (6)	0.0229 (5)	0.0167 (5)	−0.0074 (5)	−0.0073 (4)	−0.0035 (4)
O1	0.069 (3)	0.0284 (17)	0.0234 (17)	−0.0170 (17)	−0.0080 (17)	−0.0037 (14)
N1	0.044 (2)	0.037 (2)	0.021 (2)	−0.0117 (19)	−0.0066 (18)	−0.0065 (17)
C1	0.050 (3)	0.033 (2)	0.023 (2)	−0.018 (2)	−0.009 (2)	−0.0052 (19)
C2	0.034 (3)	0.039 (3)	0.019 (2)	−0.009 (2)	−0.0034 (19)	−0.0090 (19)
C3	0.034 (3)	0.034 (2)	0.022 (2)	−0.005 (2)	−0.0081 (19)	−0.0022 (19)
C4	0.033 (3)	0.042 (3)	0.020 (2)	−0.012 (2)	−0.0041 (19)	−0.010 (2)
C5	0.036 (3)	0.034 (3)	0.031 (3)	−0.002 (2)	−0.006 (2)	−0.007 (2)
C6	0.033 (3)	0.052 (3)	0.030 (3)	−0.001 (2)	−0.010 (2)	−0.006 (2)
C7	0.039 (3)	0.047 (3)	0.024 (2)	−0.009 (2)	−0.013 (2)	−0.007 (2)
C8	0.074 (4)	0.036 (3)	0.039 (3)	−0.017 (3)	−0.015 (3)	0.002 (2)
C9	0.022 (2)	0.023 (2)	0.023 (2)	−0.0053 (17)	−0.0038 (17)	−0.0068 (17)
C10	0.047 (3)	0.030 (2)	0.021 (2)	−0.016 (2)	−0.018 (2)	0.0012 (18)
C11	0.054 (3)	0.038 (3)	0.027 (3)	−0.009 (2)	−0.017 (2)	−0.002 (2)
C12	0.047 (3)	0.025 (2)	0.022 (2)	−0.012 (2)	−0.003 (2)	−0.0001 (18)
C13	0.032 (3)	0.029 (2)	0.047 (3)	−0.010 (2)	−0.003 (2)	−0.015 (2)
C14	0.039 (3)	0.028 (2)	0.023 (2)	−0.007 (2)	−0.014 (2)	−0.0072 (18)
C15	0.029 (2)	0.035 (2)	0.025 (2)	−0.0115 (19)	−0.0122 (19)	−0.0060 (19)
C16	0.041 (3)	0.042 (3)	0.038 (3)	−0.017 (2)	−0.018 (2)	0.008 (2)
C17	0.039 (3)	0.072 (4)	0.047 (3)	−0.034 (3)	−0.017 (3)	0.021 (3)
C18	0.026 (3)	0.087 (5)	0.036 (3)	−0.008 (3)	−0.005 (2)	−0.010 (3)
C19	0.036 (3)	0.062 (4)	0.034 (3)	−0.006 (3)	−0.011 (2)	−0.017 (3)
C20	0.030 (3)	0.041 (3)	0.032 (3)	−0.008 (2)	−0.011 (2)	−0.011 (2)
C21	0.030 (2)	0.022 (2)	0.018 (2)	−0.0034 (17)	−0.0083 (17)	−0.0027 (16)
C22	0.034 (3)	0.039 (3)	0.022 (2)	−0.004 (2)	−0.007 (2)	0.000 (2)
C23	0.030 (3)	0.044 (3)	0.036 (3)	−0.002 (2)	−0.012 (2)	0.004 (2)
C24	0.038 (3)	0.048 (3)	0.031 (3)	−0.008 (2)	−0.019 (2)	0.001 (2)
C25	0.039 (3)	0.058 (3)	0.021 (2)	−0.009 (3)	−0.010 (2)	−0.007 (2)
C26	0.026 (2)	0.042 (3)	0.028 (2)	−0.003 (2)	−0.004 (2)	−0.010 (2)

Au—P1	2.2416 (11)	C11—H11	0.9400
Au—S1	2.2902 (13)	C12—C13	1.348 (8)
Cl1—C4	1.731 (5)	C12—H12	0.9400
S1—C1	1.760 (5)	C13—C14	1.402 (6)
P1—C21	1.809 (5)	C13—H13	0.9400
P1—C9	1.813 (4)	C14—H14	0.9400
P1—C15	1.817 (5)	C15—C20	1.380 (7)
O1—C1	1.355 (6)	C15—C16	1.385 (6)
O1—C8	1.401 (6)	C16—C17	1.388 (8)
N1—C1	1.241 (6)	C16—H16	0.9400
N1—C2	1.418 (6)	C17—C18	1.367 (9)
C2—C7	1.374 (7)	C17—H17	0.9400
C2—C3	1.402 (7)	C18—C19	1.369 (8)
C3—C4	1.390 (7)	C18—H18	0.9400
C3—H3	0.9400	C19—C20	1.393 (7)
C4—C5	1.394 (7)	C19—H19	0.9400
C5—C6	1.372 (8)	C20—H20	0.9400
C5—H5	0.9400	C21—C22	1.404 (7)
C6—C7	1.384 (7)	C21—C26	1.406 (6)
C6—H6	0.9400	C22—C23	1.368 (8)
C7—H7	0.9400	C22—H22	0.9400
C8—H8A	0.9700	C23—C24	1.407 (7)
C8—H8B	0.9700	C23—H23	0.9400
C8—H8C	0.9700	C24—C25	1.362 (7)
C9—C14	1.375 (6)	C24—H24	0.9400
C9—C10	1.408 (6)	C25—C26	1.366 (7)
C10—C11	1.365 (7)	C25—H25	0.9400
C10—H10	0.9400	C26—H26	0.9400
C11—C12	1.376 (7)
P1—Au—S1	174.61 (4)	C13—C12—C11	120.3 (5)
C1—S1—Au	102.46 (16)	C13—C12—H12	119.8
C21—P1—C9	105.6 (2)	C11—C12—H12	119.8
C21—P1—C15	104.4 (2)	C12—C13—C14	120.4 (5)
C9—P1—C15	105.7 (2)	C12—C13—H13	119.8
C21—P1—Au	115.81 (14)	C14—C13—H13	119.8
C9—P1—Au	107.75 (14)	C9—C14—C13	119.7 (4)
C15—P1—Au	116.62 (15)	C9—C14—H14	120.1
C1—O1—C8	116.8 (4)	C13—C14—H14	120.1
C1—N1—C2	120.4 (4)	C20—C15—C16	119.6 (5)
N1—C1—O1	120.4 (4)	C20—C15—P1	121.9 (4)
N1—C1—S1	126.6 (4)	C16—C15—P1	118.6 (4)
O1—C1—S1	113.0 (3)	C15—C16—C17	119.6 (5)
C7—C2—C3	119.4 (5)	C15—C16—H16	120.2
C7—C2—N1	121.4 (5)	C17—C16—H16	120.2
C3—C2—N1	118.8 (5)	C18—C17—C16	120.4 (5)
C4—C3—C2	118.9 (5)	C18—C17—H17	119.8
C4—C3—H3	120.6	C16—C17—H17	119.8
C2—C3—H3	120.6	C17—C18—C19	120.6 (5)
C3—C4—C5	121.4 (5)	C17—C18—H18	119.7
C3—C4—Cl1	118.7 (4)	C19—C18—H18	119.7
C5—C4—Cl1	119.9 (4)	C18—C19—C20	119.6 (5)
C6—C5—C4	118.5 (5)	C18—C19—H19	120.2
C6—C5—H5	120.8	C20—C19—H19	120.2
C4—C5—H5	120.8	C15—C20—C19	120.3 (5)
C5—C6—C7	120.9 (5)	C15—C20—H20	119.9
C5—C6—H6	119.6	C19—C20—H20	119.9
C7—C6—H6	119.6	C22—C21—C26	118.3 (4)
C2—C7—C6	120.9 (5)	C22—C21—P1	118.6 (3)
C2—C7—H7	119.6	C26—C21—P1	123.1 (4)
C6—C7—H7	119.6	C23—C22—C21	120.3 (5)
O1—C8—H8A	109.5	C23—C22—H22	119.8
O1—C8—H8B	109.5	C21—C22—H22	119.8
H8A—C8—H8B	109.5	C22—C23—C24	119.9 (5)
O1—C8—H8C	109.5	C22—C23—H23	120.0
H8A—C8—H8C	109.5	C24—C23—H23	120.0
H8B—C8—H8C	109.5	C25—C24—C23	120.0 (5)
C14—C9—C10	119.2 (4)	C25—C24—H24	120.0
C14—C9—P1	123.0 (4)	C23—C24—H24	120.0
C10—C9—P1	117.8 (3)	C24—C25—C26	120.7 (5)
C11—C10—C9	119.5 (4)	C24—C25—H25	119.7
C11—C10—H10	120.2	C26—C25—H25	119.7
C9—C10—H10	120.2	C25—C26—C21	120.7 (5)
C10—C11—C12	120.8 (5)	C25—C26—H26	119.6
C10—C11—H11	119.6	C21—C26—H26	119.6
C12—C11—H11	119.6
P1—Au—S1—C1	−8.4 (7)	C11—C12—C13—C14	−0.6 (8)
S1—Au—P1—C21	−104.7 (7)	C10—C9—C14—C13	0.5 (7)
S1—Au—P1—C9	13.3 (7)	P1—C9—C14—C13	178.8 (3)
S1—Au—P1—C15	131.8 (7)	C12—C13—C14—C9	0.6 (7)
C2—N1—C1—O1	175.9 (5)	C21—P1—C15—C20	95.9 (4)
C2—N1—C1—S1	−5.4 (8)	C9—P1—C15—C20	−15.2 (5)
C8—O1—C1—N1	−6.2 (8)	Au—P1—C15—C20	−134.9 (4)
C8—O1—C1—S1	175.0 (4)	C21—P1—C15—C16	−82.6 (4)
Au—S1—C1—N1	166.0 (5)	C9—P1—C15—C16	166.2 (4)
Au—S1—C1—O1	−15.3 (4)	Au—P1—C15—C16	46.6 (4)
C1—N1—C2—C7	−75.8 (7)	C20—C15—C16—C17	−1.3 (8)
C1—N1—C2—C3	111.4 (6)	P1—C15—C16—C17	177.3 (4)
C7—C2—C3—C4	2.6 (7)	C15—C16—C17—C18	1.8 (9)
N1—C2—C3—C4	175.6 (4)	C16—C17—C18—C19	−1.9 (10)
C2—C3—C4—C5	0.2 (7)	C17—C18—C19—C20	1.5 (9)
C2—C3—C4—Cl1	179.8 (3)	C16—C15—C20—C19	0.9 (8)
C3—C4—C5—C6	−2.2 (7)	P1—C15—C20—C19	−177.6 (4)
Cl1—C4—C5—C6	178.2 (4)	C18—C19—C20—C15	−1.0 (8)
C4—C5—C6—C7	1.4 (8)	C9—P1—C21—C22	−65.8 (4)
C3—C2—C7—C6	−3.4 (7)	C15—P1—C21—C22	−177.0 (4)
N1—C2—C7—C6	−176.2 (5)	Au—P1—C21—C22	53.3 (4)
C5—C6—C7—C2	1.4 (8)	C9—P1—C21—C26	113.8 (4)
C21—P1—C9—C14	−14.8 (4)	C15—P1—C21—C26	2.6 (4)
C15—P1—C9—C14	95.5 (4)	Au—P1—C21—C26	−127.1 (4)
Au—P1—C9—C14	−139.1 (3)	C26—C21—C22—C23	−2.0 (7)
C21—P1—C9—C10	163.6 (4)	P1—C21—C22—C23	177.6 (4)
C15—P1—C9—C10	−86.1 (4)	C21—C22—C23—C24	2.0 (8)
Au—P1—C9—C10	39.2 (4)	C22—C23—C24—C25	−0.3 (9)
C14—C9—C10—C11	−1.5 (7)	C23—C24—C25—C26	−1.4 (9)
P1—C9—C10—C11	−180.0 (4)	C24—C25—C26—C21	1.4 (8)
C9—C10—C11—C12	1.6 (8)	C22—C21—C26—C25	0.4 (7)
C10—C11—C12—C13	−0.5 (8)	P1—C21—C26—C25	−179.2 (4)

Cg1 and Cg2 are the centroids of the C2–C7 and C9–C14 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12···Cg1i	0.94	2.82	3.472 (6)	127
C22—H22···Cg1ii	0.94	2.72	3.565 (5)	149
C6—H6···Cg2ii	0.94	2.97	3.615 (7)	127

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C2–C7 and C9–C14 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C12—H12⋯Cg1i	0.94	2.82	3.472 (6)	127
C22—H22⋯Cg1ii	0.94	2.72	3.565 (5)	149
C6—H6⋯Cg2ii	0.94	2.97	3.615 (7)	127

Symmetry codes: (i) ; (ii) .