[(Z)-N-(3-Chloro­phen­yl)-O-ethyl­thio­carbamato-κS](triphenyl­phosphine-κP)gold(I)

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

doi:10.1107/S1600536809049551

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 12| December 2009| Page m1663

doi:10.1107/S1600536809049551

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[(Z)-N-(3-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 17 November 2009; accepted 19 November 2009; online 25 November 2009)

The title compound, [Au(C₉H₉ClNOS)(C₁₈H₁₅P)], 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 thiocarbamato 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_r = 673.92
Triclinic, $[P \overline 1]$
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[F² > 2σ(F²)] = 0.027
wR(F²) = 0.065
S = 1.03
5662 reflections
298 parameters
H-atom parameters constrained
Δρ_max = 1.79 e Å⁻³
Δρ_min = −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 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809049551/ci2966sup1.cif

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

checkCIF report

Comment top

Systematic studies of phosphinegold(I) thiocarbamides (Ho et al. 2006; Ho & Tiekink, 2007; Kuan et al., 2008), have been motivated by delineating crystal packing characteristics of these compounds, e.g. the propensity to form aurophilic (Au···Au) interactions, as well as examining their luminescence characteristics. The title compound, (C₅H₅)₃PAu[SC(OEt)N(C₆H₄Cl-o)], was synthesized during the course of these studies.

The thiocarbamato anion functions as a thiolate ligand as seen in the magnitudes of the C1—S1 and C1═N1 bond distances of 1.759 (4) and 1.265 (4) Å, respectively; the conformation about the C1═N1 double bond is Z. The central SC(O)N chromophore is planar as seen in the S1–C1–N1–C2 and O1–C1–N1–C2 torsion angles of 2.0 (5) and -179.7 (3) °, respectively. The N-bound aryl ring is twisted out of this plane as seen in the C1–N1–C2–C3 torsion angle of 60.1 (5)°. The thiocarbamato and phosphine ligands define a S,P donor set. The deviation of the S1—Au—P1 angle [175.86 (3)°] from linearity is ascribed to the close approach of the O1 atom [2.967 (3) Å] to Au.

The crystal structure is dominated by π···π and C—H···π interactions. Centrosymmetrically related C16–C21 rings form π···π contacts: the Cg···Cgⁱ distance is 3.534 (2) Å; symmetry code (i) 1 - x, -y, -z. Two short C—H···π contacts are also noted, viz. C7—H7···Cg(C22—C27)ⁱⁱ = 2.77 Å, C7···Cg(C22—C27)ⁱⁱ = 3.630 (5) Å with an angle at H7 = 152 °; and C26—H26···Cg(C10—C15)ⁱⁱⁱ = 2.68 Å, C26···Cg(C10—C15)ⁱⁱⁱ = 3.560 (4) Å with an angle at H26 = 156 °; symmetry codes (ii) -x, 1 - y, -z; (iii) -x, -y, -1 - z.

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

The title compound 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. The molecular structure of the title compound, showing atom-labelling scheme and displacement ellipsoids at the 50% probability level.

[(Z)-N-(3-Chlorophenyl)-O-ethylthiocarbamato- κS](triphenylphosphine-κP)gold(I) top

Crystal data top

[Au(C₉H₉ClNOS)(C₁₈H₁₅P)]	Z = 2
M_r = 673.92	F(000) = 656
Triclinic, P1	D_x = 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

Data collection top

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

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)] = 0.027	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.065	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0376P)²] where P = (F_o² + 2F_c²)/3
5662 reflections	(Δ/σ)_max = 0.001
298 parameters	Δρ_max = 1.79 e Å⁻³
0 restraints	Δρ_min = −0.51 e Å⁻³

Crystal data top

[Au(C₉H₉ClNOS)(C₁₈H₁₅P)]	γ = 97.481 (1)°
M_r = 673.92	V = 1239.52 (10) Å³
Triclinic, P1	Z = 2
a = 8.7561 (4) Å	Mo Kα radiation
b = 12.3514 (6) Å	µ = 6.21 mm⁻¹
c = 13.0432 (6) Å	T = 223 K
α = 110.076 (1)°	0.11 × 0.10 × 0.05 mm
β = 105.289 (1)°

Data collection top

Bruker SMART CCD area-detector diffractometer	5662 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2000)	5184 reflections with I > 2σ(I)
T_min = 0.620, T_max = 1	R_int = 0.022
10396 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.027	0 restraints
wR(F²) = 0.065	H-atom parameters constrained
S = 1.03	Δρ_max = 1.79 e Å⁻³
5662 reflections	Δρ_min = −0.51 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	0.129193 (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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Experimental details

Crystal data
Chemical formula	[Au(C₉H₉ClNOS)(C₁₈H₁₅P)]
M_r	673.92
Crystal system, space group	Triclinic, P1
Temperature (K)	223
a, b, c (Å)	8.7561 (4), 12.3514 (6), 13.0432 (6)
α, β, γ (°)	110.076 (1), 105.289 (1), 97.481 (1)
V (Å³)	1239.52 (10)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	6.21
Crystal size (mm)	0.11 × 0.10 × 0.05

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2000)
T_min, T_max	0.620, 1
No. of measured, independent and observed [I > 2σ(I)] reflections	10396, 5662, 5184
R_int	0.022
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.027, 0.065, 1.03
No. of reflections	5662
No. of parameters	298
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.79, −0.51

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).

Acknowledgements

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

References

Beurskens, P. T., Admiraal, G., Beurskens, G., Bosman, W. P., Garcia-Granda, S., Gould, R. O., Smits, J. M. M. & Smykalla, C. (1992). The DIRDIF Program System. Technical Report. Crystallography Laboratory, University of Nijmegen, The Netherlands. Google Scholar
Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Bruker (2000). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Hall, V. J., Siasios, G. & Tiekink, E. R. T. (1993). Aust. J. Chem. 46, 561–570. CSD CrossRef CAS Google Scholar
Ho, S. Y., Cheng, E. C.-C., Tiekink, E. R. T. & Yam, V. W.-W. (2006). Inorg. Chem. 45, 8165–8174. Web of Science CSD CrossRef PubMed CAS Google Scholar
Ho, S. Y. & Tiekink, E. R. T. (2007). CrystEngComm, 9, 368–378. Web of Science CSD CrossRef CAS Google Scholar
Kuan, F. S., Ho, S. Y., Tadbuppa, P. P. & Tiekink, E. R. T. (2008). CrystEngComm, 10, 548–564. Web of Science CSD CrossRef CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Westrip, S. P. (2009). publCIF. In preparation. Google Scholar

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