[(Z)-N-(2-Chloro­phen­yl)-O-ethyl­thio­carbamato-κS](triphenyl­phosphine-κP)gold(I)

Tadbuppa, P.P.; Tiekink, E.R.T.

doi:10.1107/S1600536809049459

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 12| December 2009| Page m1683

doi:10.1107/S1600536809049459

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[(Z)-N-(2-Chlorophenyl)-O-ethylthiocarbamato-κS](triphenylphosphine-κP)gold(I)

Primjira P. Tadbuppa ^a and Edward R. T. Tiekink ^b ^*

^aDepartment of Chemistry, National University of Singapore, Singapore 117543, and ^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: edward.tiekink@gmail.com

(Received 18 November 2009; accepted 19 November 2009; online 25 November 2009)

The title compound, [Au(C₉H₉ClNOS)(C₁₈H₁₅P)], features a linear S,P-donor set with a small deviation from the ideal linear geometry due to the proximity of the methoxy O atom to Au [Au⋯O = 2.986 (4) 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_r = 673.92
Monoclinic, P 2₁ /n
a = 8.8401 (5) Å
b = 26.0187 (14) Å
c = 10.8595 (6) Å
β = 94.850 (1)°
V = 2488.8 (2) Å³
Z = 4
Mo Kα radiation
μ = 6.19 mm⁻¹
T = 223 K
0.32 × 0.16 × 0.02 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2000 ) T_min = 0.410, T_max = 1
17516 measured reflections
5712 independent reflections
4803 reflections with I > 2σ(I)
R_int = 0.049

Refinement

R[F² > 2σ(F²)] = 0.035
wR(F²) = 0.102
S = 1.03
5712 reflections
298 parameters
H-atom parameters constrained
Δρ_max = 1.69 e Å⁻³
Δρ_min = −0.98 e Å⁻³

Table 1
Selected geometric parameters (Å, °)

Au—S1	2.3131 (11)
Au—P1	2.2574 (11)

S1—Au—P1	177.45 (4)

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 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809049459/sj2690sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809049459/sj2690Isup2.hkl

checkCIF report

Comment top

As a part of systematic studies of phosphinegold(I) thiocarbamides (Ho et al. 2006; Ho & Tiekink, 2007; Kuan et al., 2008), the title compound, (C₅H₅)₃PAu[SC(OEt)N(C₆H₄Cl-o)], was synthesized, (I). In (I), Fig. 1, the thiocarbamide functions as a thiolate ligand, a conclusion confirmed by the magnitudes of the C1—S1 and C1═N1 bond distances of 1.759 (5) and 1.265 (6) Å, respectively; the conformation about C1N1 is Z. A twist is evident between the central SC(O)N chromophore (maximum deviation = 0.021 (5) Å for the C1 atom) and the N-bound aryl ring as seen in the C1–N1–C2–C3 torsion angle of -133.7 (5)°. The thiocarbamato and phosphine ligands define an S, P donor set, Table 1. The deviation of the S1—Au—P1 angle [177.45 (4) °] from linearity is ascribed to the close approach of the O1 atom to Au [2.986 (4) Å].

Related literature top

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 top

Compound (I) was prepared following the standard literature procedure from the reaction of Ph₃AuCl and EtOC(S)N(H)(C₆H₄Cl-o) in the presence of base (Hall et al., 1993).

Computing details top

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).

Figures top

Fig. 1. Molecular structure of (I) showing atom-labelling scheme and displacement ellipsoids at the 50% probability level.

[(Z)-N-(2-Chlorophenyl)-O-ethylthiocarbamato- κS](triphenylphosphine-κP)gold(I) top

Crystal data top

[Au(C₉H₉ClNOS)(C₁₈H₁₅P)]	F(000) = 1312
M_r = 673.92	D_x = 1.799 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71069 Å
Hall symbol: -P 2yn	Cell parameters from 5468 reflections
a = 8.8401 (5) Å	θ = 2.5–28.2°
b = 26.0187 (14) Å	µ = 6.19 mm⁻¹
c = 10.8595 (6) Å	T = 223 K
β = 94.850 (1)°	Plate, colourless
V = 2488.8 (2) Å³	0.32 × 0.16 × 0.02 mm
Z = 4

Data collection top

Bruker SMART CCD diffractometer	5712 independent reflections
Radiation source: fine-focus sealed tube	4803 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.049
ω scans	θ_max = 27.5°, θ_min = 1.6°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −9→11
T_min = 0.410, T_max = 1	k = −33→32
17516 measured reflections	l = −14→13

Refinement top

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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.102	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0543P)²] where P = (F_o² + 2F_c²)/3
5712 reflections	(Δ/σ)_max = 0.001
298 parameters	Δρ_max = 1.69 e Å⁻³
0 restraints	Δρ_min = −0.98 e Å⁻³

Crystal data top

[Au(C₉H₉ClNOS)(C₁₈H₁₅P)]	V = 2488.8 (2) Å³
M_r = 673.92	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 8.8401 (5) Å	µ = 6.19 mm⁻¹
b = 26.0187 (14) Å	T = 223 K
c = 10.8595 (6) Å	0.32 × 0.16 × 0.02 mm
β = 94.850 (1)°

Data collection top

Bruker SMART CCD diffractometer	5712 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2000)	4803 reflections with I > 2σ(I)
T_min = 0.410, T_max = 1	R_int = 0.049
17516 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.035	0 restraints
wR(F²) = 0.102	H-atom parameters constrained
S = 1.03	Δρ_max = 1.69 e Å⁻³
5712 reflections	Δρ_min = −0.98 e Å⁻³
298 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Au	0.239069 (19)	0.104287 (7)	0.092536 (15)	0.03276 (8)
Cl1	0.91579 (15)	0.17981 (6)	−0.11081 (11)	0.0464 (3)
S1	0.36556 (14)	0.14702 (5)	−0.05484 (10)	0.0355 (3)
P1	0.12476 (13)	0.06311 (5)	0.24242 (10)	0.0306 (3)
O1	0.5141 (4)	0.16861 (14)	0.1570 (3)	0.0367 (8)
N1	0.6231 (5)	0.20353 (17)	−0.0042 (4)	0.0376 (9)
C1	0.5152 (5)	0.1776 (2)	0.0337 (4)	0.0344 (10)
C2	0.6273 (5)	0.2179 (2)	−0.1288 (4)	0.0351 (10)
C3	0.7614 (5)	0.21131 (19)	−0.1871 (4)	0.0337 (10)
C4	0.7746 (6)	0.2294 (2)	−0.3057 (4)	0.0405 (11)
H4	0.8658	0.2246	−0.3429	0.049*
C5	0.6550 (6)	0.2542 (2)	−0.3693 (5)	0.0429 (12)
H5	0.6635	0.2663	−0.4500	0.051*
C6	0.5227 (6)	0.2612 (2)	−0.3132 (5)	0.0440 (12)
H6	0.4403	0.2781	−0.3563	0.053*
C7	0.5093 (6)	0.2439 (2)	−0.1948 (5)	0.0418 (12)
H7	0.4184	0.2497	−0.1579	0.050*
C8	0.6417 (6)	0.1891 (2)	0.2348 (5)	0.0462 (13)
H8A	0.6378	0.2267	0.2348	0.055*
H8B	0.7373	0.1784	0.2029	0.055*
C9	0.6343 (8)	0.1697 (3)	0.3603 (5)	0.073 (2)
H9A	0.7201	0.1826	0.4128	0.110*
H9B	0.6371	0.1324	0.3595	0.110*
H9C	0.5406	0.1811	0.3921	0.110*
C10	0.2264 (5)	0.00525 (19)	0.2929 (4)	0.0328 (10)
C11	0.2483 (6)	−0.0325 (2)	0.2058 (5)	0.0456 (13)
H11	0.2094	−0.0276	0.1233	0.055*
C12	0.3266 (7)	−0.0772 (2)	0.2384 (6)	0.0520 (14)
H12	0.3398	−0.1025	0.1784	0.062*
C13	0.3852 (7)	−0.0848 (2)	0.3588 (7)	0.0558 (16)
H13	0.4391	−0.1150	0.3809	0.067*
C14	0.3644 (6)	−0.0479 (2)	0.4462 (6)	0.0526 (15)
H14	0.4027	−0.0532	0.5286	0.063*
C15	0.2867 (6)	−0.0026 (2)	0.4131 (5)	0.0442 (13)
H15	0.2752	0.0228	0.4732	0.053*
C16	0.1206 (6)	0.10257 (17)	0.3797 (4)	0.0319 (10)
C17	0.2334 (6)	0.1390 (2)	0.4037 (5)	0.0439 (12)
H17	0.3034	0.1450	0.3448	0.053*
C18	0.2451 (7)	0.1666 (2)	0.5129 (5)	0.0498 (14)
H18	0.3229	0.1910	0.5285	0.060*
C19	0.1414 (7)	0.1580 (2)	0.5989 (5)	0.0465 (13)
H19	0.1498	0.1760	0.6742	0.056*
C20	0.0255 (7)	0.1231 (2)	0.5749 (5)	0.0465 (13)
H20	−0.0474	0.1184	0.6320	0.056*
C21	0.0165 (7)	0.0948 (2)	0.4661 (5)	0.0443 (13)
H21	−0.0607	0.0702	0.4511	0.053*
C22	−0.0695 (5)	0.04190 (18)	0.2042 (4)	0.0311 (9)
C23	−0.1225 (6)	−0.0036 (2)	0.2526 (5)	0.0455 (13)
H23	−0.0565	−0.0245	0.3032	0.055*
C24	−0.2714 (6)	−0.0178 (3)	0.2264 (5)	0.0538 (15)
H24	−0.3072	−0.0485	0.2595	0.065*
C25	−0.3683 (6)	0.0124 (3)	0.1522 (5)	0.0506 (14)
H25	−0.4700	0.0025	0.1346	0.061*
C26	−0.3165 (6)	0.0573 (2)	0.1034 (5)	0.0472 (13)
H26	−0.3831	0.0781	0.0531	0.057*
C27	−0.1665 (6)	0.0718 (2)	0.1284 (5)	0.0389 (11)
H27	−0.1307	0.1021	0.0937	0.047*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Au	0.03321 (12)	0.03459 (13)	0.03128 (12)	−0.00426 (7)	0.00752 (8)	0.00257 (7)
Cl1	0.0390 (6)	0.0635 (9)	0.0364 (6)	0.0048 (6)	0.0010 (5)	0.0004 (6)
S1	0.0370 (6)	0.0421 (7)	0.0278 (5)	−0.0071 (5)	0.0054 (4)	0.0029 (5)
P1	0.0301 (6)	0.0316 (6)	0.0307 (5)	−0.0039 (5)	0.0064 (5)	0.0022 (5)
O1	0.0388 (18)	0.043 (2)	0.0284 (15)	−0.0089 (15)	0.0051 (14)	0.0008 (14)
N1	0.038 (2)	0.041 (2)	0.0341 (19)	−0.0061 (18)	0.0068 (17)	0.0066 (18)
C1	0.036 (2)	0.040 (3)	0.028 (2)	−0.001 (2)	0.0068 (19)	−0.001 (2)
C2	0.036 (2)	0.038 (3)	0.032 (2)	−0.006 (2)	0.0055 (19)	0.006 (2)
C3	0.031 (2)	0.036 (3)	0.034 (2)	−0.0022 (19)	0.0021 (18)	−0.002 (2)
C4	0.043 (3)	0.042 (3)	0.039 (2)	−0.007 (2)	0.010 (2)	−0.001 (2)
C5	0.053 (3)	0.039 (3)	0.037 (2)	−0.005 (2)	0.004 (2)	0.008 (2)
C6	0.052 (3)	0.035 (3)	0.045 (3)	0.002 (2)	0.005 (2)	0.013 (2)
C7	0.040 (3)	0.037 (3)	0.050 (3)	0.000 (2)	0.011 (2)	0.011 (2)
C8	0.049 (3)	0.050 (3)	0.038 (3)	−0.011 (3)	−0.003 (2)	0.002 (2)
C9	0.070 (5)	0.110 (6)	0.040 (3)	−0.031 (4)	−0.003 (3)	0.007 (4)
C10	0.028 (2)	0.033 (3)	0.037 (2)	−0.0068 (18)	0.0070 (18)	0.001 (2)
C11	0.049 (3)	0.045 (3)	0.043 (3)	0.002 (2)	0.010 (2)	0.004 (2)
C12	0.056 (3)	0.029 (3)	0.074 (4)	0.000 (2)	0.025 (3)	−0.002 (3)
C13	0.040 (3)	0.041 (3)	0.087 (5)	0.004 (2)	0.008 (3)	0.016 (3)
C14	0.046 (3)	0.049 (4)	0.060 (3)	−0.003 (3)	−0.009 (3)	0.018 (3)
C15	0.047 (3)	0.040 (3)	0.045 (3)	−0.007 (2)	−0.002 (2)	0.002 (2)
C16	0.036 (2)	0.028 (2)	0.033 (2)	0.0018 (18)	0.0050 (19)	0.0028 (18)
C17	0.045 (3)	0.041 (3)	0.047 (3)	−0.012 (2)	0.010 (2)	−0.006 (2)
C18	0.051 (3)	0.046 (3)	0.053 (3)	−0.012 (3)	0.004 (3)	−0.015 (3)
C19	0.057 (3)	0.041 (3)	0.042 (3)	0.010 (3)	0.006 (2)	−0.008 (2)
C20	0.059 (3)	0.041 (3)	0.043 (3)	0.002 (3)	0.024 (3)	0.000 (2)
C21	0.048 (3)	0.042 (3)	0.045 (3)	−0.007 (2)	0.018 (2)	0.000 (2)
C22	0.030 (2)	0.031 (2)	0.033 (2)	−0.0043 (18)	0.0058 (18)	−0.0025 (19)
C23	0.039 (3)	0.045 (3)	0.052 (3)	−0.011 (2)	−0.002 (2)	0.011 (3)
C24	0.046 (3)	0.055 (4)	0.060 (3)	−0.020 (3)	0.001 (3)	0.011 (3)
C25	0.031 (3)	0.068 (4)	0.053 (3)	−0.008 (3)	0.003 (2)	−0.012 (3)
C26	0.040 (3)	0.052 (3)	0.048 (3)	0.011 (3)	−0.005 (2)	−0.002 (3)
C27	0.040 (3)	0.036 (3)	0.040 (2)	0.005 (2)	0.003 (2)	0.000 (2)

Geometric parameters (Å, º) top

Au—S1	2.3131 (11)	C11—H11	0.9400
Au—P1	2.2574 (11)	C12—C13	1.379 (9)
Cl1—C3	1.740 (5)	C12—H12	0.9400
S1—C1	1.759 (5)	C13—C14	1.372 (9)
P1—C16	1.813 (5)	C13—H13	0.9400
P1—C10	1.814 (5)	C14—C15	1.396 (8)
P1—C22	1.818 (5)	C14—H14	0.9400
O1—C1	1.360 (5)	C15—H15	0.9400
O1—C8	1.453 (6)	C16—C17	1.384 (7)
N1—C1	1.265 (6)	C16—C21	1.384 (7)
N1—C2	1.407 (6)	C17—C18	1.383 (7)
C2—C7	1.391 (7)	C17—H17	0.9400
C2—C3	1.401 (6)	C18—C19	1.382 (8)
C3—C4	1.385 (7)	C18—H18	0.9400
C4—C5	1.375 (7)	C19—C20	1.377 (8)
C4—H4	0.9400	C19—H19	0.9400
C5—C6	1.376 (7)	C20—C21	1.388 (8)
C5—H5	0.9400	C20—H20	0.9400
C6—C7	1.377 (7)	C21—H21	0.9400
C6—H6	0.9400	C22—C27	1.378 (7)
C7—H7	0.9400	C22—C23	1.392 (7)
C8—C9	1.460 (7)	C23—C24	1.374 (7)
C8—H8A	0.9800	C23—H23	0.9400
C8—H8B	0.9800	C24—C25	1.374 (8)
C9—H9A	0.9700	C24—H24	0.9400
C9—H9B	0.9700	C25—C26	1.376 (9)
C9—H9C	0.9700	C25—H25	0.9400
C10—C15	1.383 (7)	C26—C27	1.384 (8)
C10—C11	1.389 (7)	C26—H26	0.9400
C11—C12	1.384 (8)	C27—H27	0.9400

S1—Au—P1	177.45 (4)	C13—C12—C11	120.1 (6)
C1—S1—Au	102.98 (16)	C13—C12—H12	120.0
C16—P1—C10	105.4 (2)	C11—C12—H12	120.0
C16—P1—C22	106.0 (2)	C14—C13—C12	119.7 (6)
C10—P1—C22	104.5 (2)	C14—C13—H13	120.2
C16—P1—Au	111.44 (16)	C12—C13—H13	120.2
C10—P1—Au	111.79 (15)	C13—C14—C15	120.3 (5)
C22—P1—Au	116.84 (15)	C13—C14—H14	119.9
C1—O1—C8	116.1 (4)	C15—C14—H14	119.9
C1—N1—C2	122.4 (4)	C10—C15—C14	120.6 (5)
N1—C1—O1	118.8 (4)	C10—C15—H15	119.7
N1—C1—S1	128.1 (4)	C14—C15—H15	119.7
O1—C1—S1	113.1 (3)	C17—C16—C21	118.8 (5)
C7—C2—C3	116.9 (4)	C17—C16—P1	118.6 (4)
C7—C2—N1	123.0 (4)	C21—C16—P1	122.4 (4)
C3—C2—N1	119.7 (4)	C18—C17—C16	121.2 (5)
C4—C3—C2	121.4 (5)	C18—C17—H17	119.4
C4—C3—Cl1	118.6 (4)	C16—C17—H17	119.4
C2—C3—Cl1	120.1 (4)	C19—C18—C17	119.3 (5)
C5—C4—C3	120.3 (5)	C19—C18—H18	120.4
C5—C4—H4	119.8	C17—C18—H18	120.4
C3—C4—H4	119.8	C20—C19—C18	120.3 (5)
C4—C5—C6	119.1 (5)	C20—C19—H19	119.9
C4—C5—H5	120.4	C18—C19—H19	119.9
C6—C5—H5	120.4	C19—C20—C21	120.0 (5)
C5—C6—C7	120.9 (5)	C19—C20—H20	120.0
C5—C6—H6	119.6	C21—C20—H20	120.0
C7—C6—H6	119.6	C16—C21—C20	120.4 (5)
C6—C7—C2	121.4 (5)	C16—C21—H21	119.8
C6—C7—H7	119.3	C20—C21—H21	119.8
C2—C7—H7	119.3	C27—C22—C23	119.6 (4)
O1—C8—C9	108.8 (5)	C27—C22—P1	119.5 (4)
O1—C8—H8A	109.9	C23—C22—P1	120.9 (4)
C9—C8—H8A	109.9	C24—C23—C22	119.9 (5)
O1—C8—H8B	109.9	C24—C23—H23	120.1
C9—C8—H8B	109.9	C22—C23—H23	120.1
H8A—C8—H8B	108.3	C25—C24—C23	120.4 (5)
C8—C9—H9A	109.5	C25—C24—H24	119.8
C8—C9—H9B	109.5	C23—C24—H24	119.8
H9A—C9—H9B	109.5	C24—C25—C26	120.1 (5)
C8—C9—H9C	109.5	C24—C25—H25	120.0
H9A—C9—H9C	109.5	C26—C25—H25	120.0
H9B—C9—H9C	109.5	C25—C26—C27	120.0 (5)
C15—C10—C11	118.3 (5)	C25—C26—H26	120.0
C15—C10—P1	123.3 (4)	C27—C26—H26	120.0
C11—C10—P1	118.4 (4)	C22—C27—C26	120.0 (5)
C12—C11—C10	121.1 (5)	C22—C27—H27	120.0
C12—C11—H11	119.5	C26—C27—H27	120.0
C10—C11—H11	119.5

C2—N1—C1—O1	−175.2 (4)	C11—C10—C15—C14	−1.4 (8)
C2—N1—C1—S1	9.1 (8)	P1—C10—C15—C14	−179.7 (4)
C8—O1—C1—N1	−1.4 (7)	C13—C14—C15—C10	1.6 (9)
C8—O1—C1—S1	174.9 (4)	C10—P1—C16—C17	93.6 (4)
Au—S1—C1—N1	175.3 (5)	C22—P1—C16—C17	−155.9 (4)
Au—S1—C1—O1	−0.6 (4)	Au—P1—C16—C17	−27.8 (5)
C1—N1—C2—C7	53.7 (8)	C10—P1—C16—C21	−81.0 (5)
C1—N1—C2—C3	−133.7 (5)	C22—P1—C16—C21	29.5 (5)
C7—C2—C3—C4	−0.8 (7)	Au—P1—C16—C21	157.6 (4)
N1—C2—C3—C4	−173.8 (5)	C21—C16—C17—C18	1.3 (8)
C7—C2—C3—Cl1	179.3 (4)	P1—C16—C17—C18	−173.5 (4)
N1—C2—C3—Cl1	6.4 (7)	C16—C17—C18—C19	−0.6 (9)
C2—C3—C4—C5	−0.1 (8)	C17—C18—C19—C20	−1.4 (9)
Cl1—C3—C4—C5	179.7 (4)	C18—C19—C20—C21	2.8 (9)
C3—C4—C5—C6	0.5 (8)	C17—C16—C21—C20	0.0 (8)
C4—C5—C6—C7	0.2 (8)	P1—C16—C21—C20	174.6 (4)
C5—C6—C7—C2	−1.2 (9)	C19—C20—C21—C16	−2.0 (9)
C3—C2—C7—C6	1.5 (8)	C16—P1—C22—C27	88.7 (4)
N1—C2—C7—C6	174.2 (5)	C10—P1—C22—C27	−160.2 (4)
C1—O1—C8—C9	−171.8 (5)	Au—P1—C22—C27	−36.1 (4)
C16—P1—C10—C15	−1.3 (5)	C16—P1—C22—C23	−89.9 (4)
C22—P1—C10—C15	−112.8 (4)	C10—P1—C22—C23	21.1 (5)
Au—P1—C10—C15	119.9 (4)	Au—P1—C22—C23	145.3 (4)
C16—P1—C10—C11	−179.6 (4)	C27—C22—C23—C24	−1.2 (8)
C22—P1—C10—C11	68.9 (4)	P1—C22—C23—C24	177.4 (5)
Au—P1—C10—C11	−58.4 (4)	C22—C23—C24—C25	0.3 (9)
C15—C10—C11—C12	0.9 (8)	C23—C24—C25—C26	0.1 (9)
P1—C10—C11—C12	179.2 (4)	C24—C25—C26—C27	0.4 (9)
C10—C11—C12—C13	−0.4 (9)	C23—C22—C27—C26	1.7 (8)
C11—C12—C13—C14	0.5 (9)	P1—C22—C27—C26	−177.0 (4)
C12—C13—C14—C15	−1.1 (9)	C25—C26—C27—C22	−1.3 (8)

Experimental details

Crystal data
Chemical formula	[Au(C₉H₉ClNOS)(C₁₈H₁₅P)]
M_r	673.92
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	223
a, b, c (Å)	8.8401 (5), 26.0187 (14), 10.8595 (6)
β (°)	94.850 (1)
V (Å³)	2488.8 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	6.19
Crystal size (mm)	0.32 × 0.16 × 0.02

Data collection
Diffractometer	Bruker SMART CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2000)
T_min, T_max	0.410, 1
No. of measured, independent and observed [I > 2σ(I)] reflections	17516, 5712, 4803
R_int	0.049
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.035, 0.102, 1.03
No. of reflections	5712
No. of parameters	298
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.69, −0.98

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SHELXTL (Sheldrick, 2008), PATTY in DIRDIF92 (Beurskens et al., 1992), SHELXL97 (Sheldrick, 2008), DIAMOND (Brandenburg, 2006), publCIF (Westrip, 2009).

Selected geometric parameters (Å, º) top

Au—S1	2.3131 (11)	Au—P1	2.2574 (11)

S1—Au—P1	177.45 (4)

Acknowledgements

The National University of Singapore (grant No. R-143–000–213–112) is thanked for support.

References

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