[(Z)-N-(4-Chloro-phen-yl)-O-methyl-thio-carbamato-κS](triphenyl-phosphine-κP)gold(I).

The title compound, [Au(C(8)H(7)ClNOS)(C(18)H(15)P)], is characterized by a linear S,P-donor set with a small deviation from the ideal linearity [S-Au-P = 175.14 (5)°] due to the close approach of the O atom to the Au atom [Au⋯O = 2.882 (3) Å]. Loosely associated dimers are formed in the crystal structure through C-H⋯O inter-actions.

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(C8H7ClNOS)(C18H15P)]

M = 659.89

Monoclinic,

a = 9.1781 (6) Å

b = 17.5679 (12) Å

c = 15.5384 (11) Å

β = 104.156 (2)°

V = 2429.3 (3) Å3

Z = 4

Mo Kα radiation

μ = 6.34 mm−1

T = 223 K

0.11 × 0.10 × 0.07 mm

Data collection

Bruker SMART APEX CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.363, T max = 1.000

17091 measured reflections

5570 independent reflections

4526 reflections with I > 2σ(I)

R int = 0.042

Refinement

R[F 2 > 2σ(F 2)] = 0.029

wR(F 2) = 0.090

S = 1.06

5570 reflections

290 parameters

H-atom parameters constrained

Δρmax = 1.17 e Å−3

Δρmin = −0.62 e Å−3

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); 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, 1999 ▶); software used to prepare material for publication: publCIF (Westrip, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809050454/hy2256sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809050454/hy2256Isup2.hkl

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

[Au(C8H7ClNOS)(C18H15P)]	F(000) = 1280
Mr = 659.89	Dx = 1.804 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71069 Å
Hall symbol: -P 2yn	Cell parameters from 4456 reflections
a = 9.1781 (6) Å	θ = 2.3–25.0°
b = 17.5679 (12) Å	µ = 6.34 mm−1
c = 15.5384 (11) Å	T = 223 K
β = 104.156 (2)°	Block, colourless
V = 2429.3 (3) Å3	0.11 × 0.10 × 0.07 mm
Z = 4

Bruker SMART APEX CCD diffractometer	5570 independent reflections
Radiation source: fine-focus sealed tube	4526 reflections with I > 2σ(I)
graphite	Rint = 0.042
φ and ω scans	θmax = 27.5°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −11→10
Tmin = 0.363, Tmax = 1.000	k = −22→22
17091 measured reflections	l = −20→14

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)] = 0.029	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.090	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0462P)2P] where P = (Fo2 + 2Fc2)/3
5570 reflections	(Δ/σ)max = 0.001
290 parameters	Δρmax = 1.17 e Å−3
0 restraints	Δρmin = −0.62 e Å−3

	x	y	z	Uiso*/Ueq
Au	0.14582 (2)	0.203115 (10)	0.426452 (12)	0.02944 (8)
Cl1	0.2539 (2)	−0.28046 (9)	0.29800 (15)	0.0761 (6)
S1	0.19317 (16)	0.07649 (7)	0.40658 (8)	0.0372 (3)
P1	0.08624 (13)	0.32352 (7)	0.45280 (8)	0.0265 (3)
O1	0.2450 (4)	0.10253 (19)	0.5758 (2)	0.0342 (8)
N1	0.2656 (4)	−0.0229 (2)	0.5444 (3)	0.0352 (9)
C1	0.2379 (5)	0.0450 (3)	0.5172 (3)	0.0303 (10)
C2	0.2605 (5)	−0.0827 (3)	0.4832 (3)	0.0350 (11)
C3	0.1251 (5)	−0.1125 (3)	0.4349 (3)	0.0378 (12)
H3	0.0343	−0.0911	0.4410	0.045*
C4	0.1222 (6)	−0.1735 (3)	0.3779 (4)	0.0428 (13)
H4	0.0304	−0.1931	0.3443	0.051*
C5	0.2552 (7)	−0.2045 (3)	0.3715 (5)	0.0461 (14)
C6	0.3906 (7)	−0.1768 (3)	0.4203 (5)	0.0507 (16)
H6	0.4809	−0.1996	0.4153	0.061*
C7	0.3939 (6)	−0.1165 (3)	0.4754 (4)	0.0434 (13)
H7	0.4866	−0.0976	0.5084	0.052*
C8	0.2730 (7)	0.0813 (4)	0.6684 (3)	0.0519 (15)
H8A	0.1966	0.0456	0.6762	0.078*
H8B	0.2699	0.1263	0.7040	0.078*
H8C	0.3712	0.0576	0.6870	0.078*
C9	0.1409 (5)	0.3443 (3)	0.5711 (3)	0.0295 (10)
C10	0.2879 (6)	0.3272 (3)	0.6162 (4)	0.0466 (14)
H10	0.3539	0.3047	0.5859	0.056*
C11	0.3363 (7)	0.3434 (4)	0.7058 (4)	0.0535 (16)
H11	0.4351	0.3316	0.7368	0.064*
C12	0.2396 (7)	0.3768 (3)	0.7492 (4)	0.0471 (14)
H12	0.2730	0.3885	0.8099	0.057*
C13	0.0944 (6)	0.3936 (3)	0.7049 (4)	0.0436 (13)
H13	0.0283	0.4159	0.7352	0.052*
C14	0.0462 (6)	0.3773 (3)	0.6154 (3)	0.0326 (11)
H14	−0.0528	0.3892	0.5848	0.039*
C15	0.1717 (5)	0.3984 (2)	0.4012 (3)	0.0267 (9)
C16	0.1530 (5)	0.3965 (3)	0.3101 (3)	0.0323 (10)
H16	0.0989	0.3563	0.2770	0.039*
C17	0.2129 (6)	0.4530 (3)	0.2673 (3)	0.0358 (11)
H17	0.1990	0.4513	0.2053	0.043*
C18	0.2926 (6)	0.5118 (3)	0.3152 (4)	0.0382 (12)
H18	0.3328	0.5506	0.2862	0.046*
C19	0.3131 (6)	0.5133 (3)	0.4061 (4)	0.0382 (12)
H19	0.3684	0.5530	0.4393	0.046*
C20	0.2532 (5)	0.4570 (3)	0.4485 (3)	0.0344 (11)
H20	0.2681	0.4586	0.5105	0.041*
C21	−0.1136 (5)	0.3406 (3)	0.4161 (3)	0.0259 (9)
C22	−0.2118 (6)	0.2803 (3)	0.4140 (4)	0.0425 (13)
H22	−0.1735	0.2315	0.4309	0.051*
C23	−0.3653 (6)	0.2911 (3)	0.3874 (5)	0.0500 (15)
H23	−0.4307	0.2499	0.3868	0.060*
C24	−0.4224 (6)	0.3617 (3)	0.3618 (4)	0.0421 (13)
H24	−0.5268	0.3689	0.3428	0.051*
C25	−0.3268 (6)	0.4219 (3)	0.3641 (3)	0.0361 (11)
H25	−0.3664	0.4705	0.3470	0.043*
C26	−0.1724 (5)	0.4122 (3)	0.3913 (3)	0.0312 (10)
H26	−0.1079	0.4540	0.3930	0.037*

	U11	U22	U33	U12	U13	U23
Au	0.03688 (12)	0.02458 (11)	0.02522 (11)	0.00819 (7)	0.00444 (8)	0.00001 (7)
Cl1	0.0969 (14)	0.0355 (8)	0.1131 (17)	−0.0060 (8)	0.0587 (13)	−0.0165 (9)
S1	0.0577 (8)	0.0266 (6)	0.0267 (6)	0.0125 (6)	0.0092 (6)	0.0013 (5)
P1	0.0296 (6)	0.0242 (6)	0.0250 (6)	0.0058 (5)	0.0050 (5)	−0.0002 (5)
O1	0.0384 (18)	0.0375 (19)	0.0250 (18)	0.0022 (15)	0.0045 (14)	0.0035 (15)
N1	0.032 (2)	0.037 (2)	0.037 (2)	0.0053 (17)	0.0106 (18)	0.0114 (19)
C1	0.028 (2)	0.036 (3)	0.027 (3)	0.0034 (19)	0.007 (2)	0.003 (2)
C2	0.035 (3)	0.028 (2)	0.043 (3)	0.003 (2)	0.013 (2)	0.012 (2)
C3	0.033 (3)	0.034 (3)	0.051 (3)	0.004 (2)	0.018 (2)	0.008 (2)
C4	0.038 (3)	0.035 (3)	0.058 (4)	−0.003 (2)	0.016 (3)	0.003 (3)
C5	0.056 (4)	0.026 (3)	0.065 (4)	0.001 (2)	0.030 (3)	0.006 (2)
C6	0.047 (3)	0.032 (3)	0.081 (5)	0.014 (2)	0.033 (3)	0.011 (3)
C7	0.032 (3)	0.040 (3)	0.061 (4)	0.006 (2)	0.019 (3)	0.015 (3)
C8	0.064 (4)	0.066 (4)	0.021 (3)	0.003 (3)	0.002 (3)	0.001 (3)
C9	0.038 (3)	0.024 (2)	0.025 (2)	0.0043 (19)	0.004 (2)	0.0020 (18)
C10	0.043 (3)	0.056 (4)	0.036 (3)	0.021 (3)	0.000 (2)	−0.006 (3)
C11	0.053 (4)	0.067 (4)	0.033 (3)	0.017 (3)	−0.005 (3)	−0.002 (3)
C12	0.067 (4)	0.043 (3)	0.025 (3)	0.001 (3)	−0.002 (3)	−0.003 (2)
C13	0.056 (3)	0.045 (3)	0.033 (3)	0.003 (3)	0.015 (3)	−0.005 (2)
C14	0.036 (3)	0.034 (3)	0.027 (3)	0.001 (2)	0.008 (2)	−0.001 (2)
C15	0.027 (2)	0.023 (2)	0.031 (2)	0.0050 (17)	0.0086 (19)	−0.0006 (19)
C16	0.036 (3)	0.029 (2)	0.030 (3)	0.003 (2)	0.004 (2)	−0.001 (2)
C17	0.040 (3)	0.039 (3)	0.029 (3)	0.006 (2)	0.011 (2)	0.003 (2)
C18	0.037 (3)	0.030 (3)	0.049 (3)	0.001 (2)	0.014 (2)	0.004 (2)
C19	0.038 (3)	0.033 (3)	0.043 (3)	−0.003 (2)	0.011 (2)	−0.003 (2)
C20	0.041 (3)	0.032 (3)	0.027 (3)	0.005 (2)	0.003 (2)	−0.003 (2)
C21	0.027 (2)	0.030 (2)	0.019 (2)	0.0047 (18)	0.0020 (18)	0.0013 (18)
C22	0.042 (3)	0.029 (3)	0.050 (3)	0.001 (2)	−0.003 (3)	0.011 (2)
C23	0.037 (3)	0.050 (4)	0.061 (4)	−0.008 (2)	0.008 (3)	0.011 (3)
C24	0.033 (3)	0.055 (4)	0.038 (3)	0.006 (2)	0.008 (2)	0.000 (3)
C25	0.041 (3)	0.032 (3)	0.033 (3)	0.012 (2)	0.004 (2)	−0.001 (2)
C26	0.033 (3)	0.030 (2)	0.029 (3)	0.0040 (19)	0.007 (2)	−0.002 (2)

Au—S1	2.3018 (12)	C11—H11	0.9400
Au—P1	2.2473 (12)	C12—C13	1.374 (8)
Cl1—C5	1.755 (6)	C12—H12	0.9400
S1—C1	1.756 (5)	C13—C14	1.381 (7)
P1—C21	1.808 (4)	C13—H13	0.9400
P1—C15	1.815 (5)	C14—H14	0.9400
P1—C9	1.820 (5)	C15—C20	1.375 (6)
O1—C1	1.352 (6)	C15—C16	1.384 (6)
O1—C8	1.447 (6)	C16—C17	1.383 (7)
N1—C1	1.271 (6)	C16—H16	0.9400
N1—C2	1.409 (7)	C17—C18	1.375 (7)
C2—C3	1.387 (7)	C17—H17	0.9400
C2—C7	1.393 (7)	C18—C19	1.380 (7)
C3—C4	1.387 (8)	C18—H18	0.9400
C3—H3	0.9400	C19—C20	1.375 (7)
C4—C5	1.362 (8)	C19—H19	0.9400
C4—H4	0.9400	C20—H20	0.9400
C5—C6	1.377 (9)	C21—C22	1.385 (7)
C6—C7	1.357 (8)	C21—C26	1.386 (6)
C6—H6	0.9400	C22—C23	1.381 (8)
C7—H7	0.9400	C22—H22	0.9400
C8—H8A	0.9700	C23—C24	1.366 (7)
C8—H8B	0.9700	C23—H23	0.9400
C8—H8C	0.9700	C24—C25	1.369 (7)
C9—C14	1.363 (7)	C24—H24	0.9400
C9—C10	1.393 (7)	C25—C26	1.387 (7)
C10—C11	1.384 (8)	C25—H25	0.9400
C10—H10	0.9400	C26—H26	0.9400
C11—C12	1.370 (8)
P1—Au—S1	175.14 (5)	C11—C12—C13	120.7 (5)
C1—S1—Au	100.35 (17)	C11—C12—H12	119.6
C21—P1—C15	104.8 (2)	C13—C12—H12	119.6
C21—P1—C9	107.1 (2)	C12—C13—C14	119.5 (5)
C15—P1—C9	105.0 (2)	C12—C13—H13	120.2
C21—P1—Au	111.82 (15)	C14—C13—H13	120.2
C15—P1—Au	116.79 (15)	C9—C14—C13	120.6 (5)
C9—P1—Au	110.73 (15)	C9—C14—H14	119.7
C1—O1—C8	116.4 (4)	C13—C14—H14	119.7
C1—N1—C2	120.3 (4)	C20—C15—C16	118.7 (4)
N1—C1—O1	120.3 (4)	C20—C15—P1	123.0 (4)
N1—C1—S1	126.9 (4)	C16—C15—P1	118.4 (3)
O1—C1—S1	112.7 (3)	C17—C16—C15	120.7 (5)
C3—C2—C7	118.8 (5)	C17—C16—H16	119.6
C3—C2—N1	121.6 (4)	C15—C16—H16	119.6
C7—C2—N1	119.4 (5)	C18—C17—C16	120.0 (5)
C4—C3—C2	120.8 (5)	C18—C17—H17	120.0
C4—C3—H3	119.6	C16—C17—H17	120.0
C2—C3—H3	119.6	C17—C18—C19	119.3 (5)
C5—C4—C3	118.5 (5)	C17—C18—H18	120.3
C5—C4—H4	120.7	C19—C18—H18	120.3
C3—C4—H4	120.7	C20—C19—C18	120.4 (5)
C4—C5—C6	121.6 (6)	C20—C19—H19	119.8
C4—C5—Cl1	119.2 (5)	C18—C19—H19	119.8
C6—C5—Cl1	119.2 (4)	C15—C20—C19	120.8 (5)
C7—C6—C5	120.1 (5)	C15—C20—H20	119.6
C7—C6—H6	120.0	C19—C20—H20	119.6
C5—C6—H6	120.0	C22—C21—C26	118.7 (4)
C6—C7—C2	120.2 (5)	C22—C21—P1	119.0 (4)
C6—C7—H7	119.9	C26—C21—P1	122.3 (4)
C2—C7—H7	119.9	C23—C22—C21	120.8 (5)
O1—C8—H8A	109.5	C23—C22—H22	119.6
O1—C8—H8B	109.5	C21—C22—H22	119.6
H8A—C8—H8B	109.5	C24—C23—C22	120.1 (5)
O1—C8—H8C	109.5	C24—C23—H23	119.9
H8A—C8—H8C	109.5	C22—C23—H23	119.9
H8B—C8—H8C	109.5	C23—C24—C25	119.7 (5)
C14—C9—C10	119.8 (5)	C23—C24—H24	120.1
C14—C9—P1	122.9 (4)	C25—C24—H24	120.1
C10—C9—P1	117.3 (4)	C24—C25—C26	120.8 (5)
C11—C10—C9	119.6 (5)	C24—C25—H25	119.6
C11—C10—H10	120.2	C26—C25—H25	119.6
C9—C10—H10	120.2	C21—C26—C25	119.7 (5)
C12—C11—C10	119.7 (5)	C21—C26—H26	120.1
C12—C11—H11	120.1	C25—C26—H26	120.1
C10—C11—H11	120.1
C2—N1—C1—O1	−179.0 (4)	P1—C9—C14—C13	−178.5 (4)
C2—N1—C1—S1	−0.8 (7)	C12—C13—C14—C9	0.6 (8)
C8—O1—C1—N1	−4.9 (6)	C21—P1—C15—C20	110.4 (4)
C8—O1—C1—S1	176.7 (4)	C9—P1—C15—C20	−2.2 (4)
Au—S1—C1—N1	175.8 (4)	Au—P1—C15—C20	−125.2 (4)
Au—S1—C1—O1	−6.0 (3)	C21—P1—C15—C16	−69.1 (4)
C1—N1—C2—C3	−76.6 (6)	C9—P1—C15—C16	178.3 (4)
C1—N1—C2—C7	108.0 (5)	Au—P1—C15—C16	55.2 (4)
C7—C2—C3—C4	−1.8 (8)	C20—C15—C16—C17	−1.0 (7)
N1—C2—C3—C4	−177.2 (5)	P1—C15—C16—C17	178.5 (4)
C2—C3—C4—C5	1.2 (8)	C15—C16—C17—C18	0.3 (7)
C3—C4—C5—C6	0.1 (9)	C16—C17—C18—C19	0.5 (8)
C3—C4—C5—Cl1	−178.7 (4)	C17—C18—C19—C20	−0.6 (8)
C4—C5—C6—C7	−0.9 (9)	C16—C15—C20—C19	0.9 (7)
Cl1—C5—C6—C7	178.0 (4)	P1—C15—C20—C19	−178.6 (4)
C5—C6—C7—C2	0.3 (9)	C18—C19—C20—C15	−0.1 (8)
C3—C2—C7—C6	1.0 (8)	C15—P1—C21—C22	155.3 (4)
N1—C2—C7—C6	176.5 (5)	C9—P1—C21—C22	−93.6 (4)
C21—P1—C9—C14	−8.7 (5)	Au—P1—C21—C22	27.9 (4)
C15—P1—C9—C14	102.3 (4)	C15—P1—C21—C26	−25.9 (4)
Au—P1—C9—C14	−130.9 (4)	C9—P1—C21—C26	85.3 (4)
C21—P1—C9—C10	173.1 (4)	Au—P1—C21—C26	−153.3 (3)
C15—P1—C9—C10	−75.9 (5)	C26—C21—C22—C23	0.3 (8)
Au—P1—C9—C10	51.0 (5)	P1—C21—C22—C23	179.2 (5)
C14—C9—C10—C11	0.4 (9)	C21—C22—C23—C24	0.6 (10)
P1—C9—C10—C11	178.6 (5)	C22—C23—C24—C25	−1.1 (10)
C9—C10—C11—C12	−0.6 (10)	C23—C24—C25—C26	0.5 (8)
C10—C11—C12—C13	0.8 (10)	C22—C21—C26—C25	−0.8 (7)
C11—C12—C13—C14	−0.8 (9)	P1—C21—C26—C25	−179.7 (4)
C10—C9—C14—C13	−0.4 (8)	C24—C25—C26—C21	0.4 (7)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O1i	0.94	2.52	3.365 (6)	150

Table 1

Selected bond lengths (Å)

Au—S1	2.3018 (12)
Au—P1	2.2473 (12)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯O1i	0.94	2.52	3.365 (6)	150

Symmetry code: (i) .