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

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

doi:10.1107/S160053680904906X

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 12| December 2009| Page m1646

doi:10.1107/S160053680904906X

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[(Z)-N-(2-Chlorophenyl)-O-methylthiocarbamato-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 18 November 2009; online 21 November 2009)

In the title compound, [Au(C₈H₇ClNOS)(C₁₈H₁₅P)], the Au^I atom has a near-linear geometry, defined by an S,P-donor set [S—Au—P = 175.09 (5)°]. The proximity of the methoxy O atom to Au may be responsible for the deviation from linearity [Au⋯O = 2.959 (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(C₈H₇ClNOS)(C₁₈H₁₅P)]
M_r = 659.89
Monoclinic, P 2₁ /n
a = 8.9388 (5) Å
b = 26.2804 (15) Å
c = 10.3233 (6) Å
β = 96.599 (1)°
V = 2409.0 (2) Å³
Z = 4
Mo Kα radiation
μ = 6.39 mm⁻¹
T = 223 K
0.13 × 0.10 × 0.07 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2000 ) T_min = 0.521, T_max = 1
17015 measured reflections
5537 independent reflections
4400 reflections with I > 2σ(I)
R_int = 0.047

Refinement

R[F² > 2σ(F²)] = 0.032
wR(F²) = 0.085
S = 1.04
5537 reflections
290 parameters
H-atom parameters constrained
Δρ_max = 1.17 e Å⁻³
Δρ_min = −0.54 e Å⁻³

Table 1
Selected bond lengths (Å)

Au—S1	2.3086 (12)
Au—P1	2.2508 (12)

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SHELXTL (Bruker, 2000); 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/S160053680904906X/hb5235sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053680904906X/hb5235Isup2.hkl

checkCIF report

Comment top

The motivation for systematic studies of phosphinegold(I) thiocarbamides, e.g. (R₃P)PAu[SC(OR')NR''], relates to the delineation of crystal packing characteristics, e.g. the propensity to form aurophilic (Au···Au) interactions (Ho & Tiekink, 2007; Kuan et al., 2008), as well as the examination of their luminescence characteristics (Ho et al. 2006). The title compound, (C₅H₅)₃PAu[SC(OMe)N(C₆H₄Cl-o)], (I), was synthesized during the course of these studies.

The thiocarbamato anion functions as a thiolate ligand in (I), Fig. 1, as seen in the magnitudes of the C1—S1 and C1═N1 bond distances of 1.762 (5) and 1.269 (6) Å, respectively; the conformation about C1═N1 is Z. The central SC(O)N chromophore has small but significant twists from planarity as seen in the S1–C1–N1–C2 and O1–C1–N1–C2 torsion angles of 10.0 (7) and -173.1 (4) °, respectively. The N-bound aryl ring is twisted out of this plane: the C1–N1–C2–C3 torsion angle is -126.3 (5) °. The thiocarbamato and phosphine ligands define an approximately linear S, P donor set, Table. The deviation of the S1—Au—P1 angle [175.09 (5) °] from the ideal linear geometry is ascribed to the close approach of the O1 atom [2.959 (4) Å] to Au.

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 MeOC(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 (Bruker, 2000); 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 displacement ellipsoids at the 50% probability level.

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

Crystal data top

[Au(C₈H₇ClNOS)(C₁₈H₁₅P)]	F(000) = 1280
M_r = 659.89	D_x = 1.819 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71069 Å
Hall symbol: -P 2yn	Cell parameters from 3828 reflections
a = 8.9388 (5) Å	θ = 2.4–24.2°
b = 26.2804 (15) Å	µ = 6.39 mm⁻¹
c = 10.3233 (6) Å	T = 223 K
β = 96.599 (1)°	Block, colourless
V = 2409.0 (2) Å³	0.13 × 0.10 × 0.07 mm
Z = 4

Data collection top

Bruker SMART CCD diffractometer	5537 independent reflections
Radiation source: fine-focus sealed tube	4400 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.047
ω scans	θ_max = 27.5°, θ_min = 1.6°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −11→10
T_min = 0.521, T_max = 1	k = −34→33
17015 measured reflections	l = −13→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)] = 0.032	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.085	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0379P)²] where P = (F_o² + 2F_c²)/3
5537 reflections	(Δ/σ)_max < 0.001
290 parameters	Δρ_max = 1.17 e Å⁻³
0 restraints	Δρ_min = −0.54 e Å⁻³

Crystal data top

[Au(C₈H₇ClNOS)(C₁₈H₁₅P)]	V = 2409.0 (2) Å³
M_r = 659.89	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 8.9388 (5) Å	µ = 6.39 mm⁻¹
b = 26.2804 (15) Å	T = 223 K
c = 10.3233 (6) Å	0.13 × 0.10 × 0.07 mm
β = 96.599 (1)°

Data collection top

Bruker SMART CCD diffractometer	5537 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2000)	4400 reflections with I > 2σ(I)
T_min = 0.521, T_max = 1	R_int = 0.047
17015 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.032	0 restraints
wR(F²) = 0.085	H-atom parameters constrained
S = 1.04	Δρ_max = 1.17 e Å⁻³
5537 reflections	Δρ_min = −0.54 e Å⁻³
290 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	0.24654 (2)	0.102793 (8)	0.096786 (18)	0.02961 (8)
Cl1	0.89614 (16)	0.17339 (6)	−0.09989 (13)	0.0446 (3)
S1	0.37239 (14)	0.14902 (5)	−0.04703 (12)	0.0313 (3)
P1	0.13681 (14)	0.06089 (5)	0.25093 (12)	0.0267 (3)
O1	0.5076 (4)	0.16834 (14)	0.1853 (3)	0.0349 (9)
N1	0.6237 (5)	0.20523 (16)	0.0254 (4)	0.0320 (10)
C1	0.5160 (5)	0.17848 (19)	0.0581 (5)	0.0283 (11)
C2	0.6239 (6)	0.22061 (19)	−0.1058 (5)	0.0299 (11)
C3	0.7475 (5)	0.21050 (19)	−0.1725 (5)	0.0301 (11)
C4	0.7550 (6)	0.2287 (2)	−0.2976 (5)	0.0390 (13)
H4	0.8395	0.2213	−0.3407	0.047*
C5	0.6403 (7)	0.2573 (2)	−0.3584 (5)	0.0405 (13)
H5	0.6450	0.2697	−0.4432	0.049*
C6	0.5180 (6)	0.2676 (2)	−0.2937 (6)	0.0428 (14)
H6	0.4379	0.2869	−0.3356	0.051*
C7	0.5101 (6)	0.2503 (2)	−0.1685 (5)	0.0384 (13)
H7	0.4265	0.2589	−0.1253	0.046*
C8	0.6204 (7)	0.1907 (3)	0.2779 (5)	0.0468 (15)
H8A	0.7169	0.1748	0.2702	0.070*
H8B	0.5936	0.1855	0.3653	0.070*
H8C	0.6271	0.2268	0.2608	0.070*
C9	0.1331 (5)	0.10132 (18)	0.3935 (5)	0.0273 (10)
C10	0.2482 (6)	0.1366 (2)	0.4224 (5)	0.0366 (13)
H10	0.3225	0.1407	0.3658	0.044*
C11	0.2530 (6)	0.1655 (2)	0.5335 (6)	0.0444 (14)
H11	0.3326	0.1885	0.5538	0.053*
C12	0.1430 (7)	0.1611 (2)	0.6157 (6)	0.0441 (15)
H12	0.1479	0.1806	0.6923	0.053*
C13	0.0248 (7)	0.1275 (2)	0.5843 (6)	0.0454 (15)
H13	−0.0527	0.1253	0.6384	0.055*
C14	0.0199 (6)	0.0975 (2)	0.4747 (5)	0.0379 (13)
H14	−0.0599	0.0745	0.4547	0.045*
C15	0.2397 (5)	0.00408 (19)	0.3076 (5)	0.0301 (11)
C16	0.2844 (6)	−0.0052 (2)	0.4394 (5)	0.0386 (13)
H16	0.2640	0.0185	0.5031	0.046*
C17	0.3602 (7)	−0.0506 (2)	0.4751 (7)	0.0510 (16)
H17	0.3904	−0.0572	0.5637	0.061*
C18	0.3912 (7)	−0.0857 (2)	0.3836 (8)	0.0551 (18)
H18	0.4414	−0.1161	0.4095	0.066*
C19	0.3488 (7)	−0.0762 (2)	0.2546 (7)	0.0526 (17)
H19	0.3709	−0.1001	0.1917	0.063*
C20	0.2728 (6)	−0.0314 (2)	0.2154 (6)	0.0422 (14)
H20	0.2440	−0.0253	0.1263	0.051*
C21	−0.0550 (5)	0.03955 (19)	0.2088 (4)	0.0262 (10)
C22	−0.1585 (6)	0.0739 (2)	0.1473 (5)	0.0367 (13)
H22	−0.1274	0.1065	0.1245	0.044*
C23	−0.3071 (6)	0.0596 (3)	0.1200 (6)	0.0470 (15)
H23	−0.3778	0.0830	0.0807	0.056*
C24	−0.3536 (6)	0.0114 (3)	0.1495 (6)	0.0462 (15)
H24	−0.4551	0.0020	0.1294	0.055*
C25	−0.2516 (6)	−0.0228 (2)	0.2083 (6)	0.0449 (14)
H25	−0.2829	−0.0558	0.2283	0.054*
C26	−0.1020 (6)	−0.0087 (2)	0.2384 (5)	0.0332 (12)
H26	−0.0322	−0.0321	0.2791	0.040*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Au	0.02941 (12)	0.03086 (12)	0.02991 (12)	−0.00652 (9)	0.00915 (8)	0.00018 (9)
Cl1	0.0407 (8)	0.0589 (10)	0.0340 (7)	0.0071 (7)	0.0033 (6)	−0.0004 (7)
S1	0.0317 (7)	0.0374 (8)	0.0257 (6)	−0.0082 (6)	0.0074 (5)	0.0005 (5)
P1	0.0265 (7)	0.0255 (7)	0.0290 (7)	−0.0051 (5)	0.0073 (5)	−0.0014 (5)
O1	0.035 (2)	0.045 (2)	0.0252 (19)	−0.0108 (17)	0.0040 (15)	0.0024 (16)
N1	0.030 (2)	0.032 (3)	0.035 (2)	−0.0076 (19)	0.0042 (19)	−0.0003 (19)
C1	0.026 (2)	0.032 (3)	0.028 (3)	−0.001 (2)	0.006 (2)	−0.004 (2)
C2	0.032 (3)	0.029 (3)	0.029 (3)	−0.009 (2)	0.004 (2)	−0.001 (2)
C3	0.032 (3)	0.027 (3)	0.030 (3)	−0.009 (2)	0.001 (2)	0.000 (2)
C4	0.038 (3)	0.045 (3)	0.036 (3)	−0.008 (3)	0.012 (2)	−0.004 (3)
C5	0.054 (4)	0.037 (3)	0.031 (3)	−0.006 (3)	0.008 (3)	0.008 (2)
C6	0.045 (3)	0.034 (3)	0.049 (4)	−0.001 (3)	0.003 (3)	0.013 (3)
C7	0.036 (3)	0.034 (3)	0.046 (3)	−0.003 (2)	0.010 (3)	0.008 (3)
C8	0.050 (4)	0.060 (4)	0.029 (3)	−0.018 (3)	−0.003 (3)	0.001 (3)
C9	0.026 (3)	0.025 (3)	0.031 (3)	0.002 (2)	0.004 (2)	0.002 (2)
C10	0.031 (3)	0.036 (3)	0.043 (3)	−0.003 (2)	0.003 (2)	−0.005 (2)
C11	0.040 (3)	0.039 (3)	0.052 (4)	−0.006 (3)	−0.004 (3)	−0.014 (3)
C12	0.060 (4)	0.034 (3)	0.036 (3)	0.012 (3)	−0.002 (3)	−0.006 (3)
C13	0.062 (4)	0.037 (3)	0.040 (3)	0.007 (3)	0.020 (3)	0.000 (3)
C14	0.042 (3)	0.035 (3)	0.039 (3)	−0.007 (3)	0.015 (3)	−0.003 (2)
C15	0.020 (2)	0.029 (3)	0.041 (3)	−0.006 (2)	0.006 (2)	−0.003 (2)
C16	0.033 (3)	0.040 (3)	0.042 (3)	0.000 (2)	−0.001 (2)	−0.002 (3)
C17	0.040 (3)	0.044 (4)	0.065 (4)	0.000 (3)	−0.009 (3)	0.013 (3)
C18	0.037 (4)	0.035 (3)	0.093 (6)	0.011 (3)	0.004 (3)	0.009 (4)
C19	0.043 (4)	0.041 (4)	0.078 (5)	0.004 (3)	0.023 (3)	−0.009 (3)
C20	0.037 (3)	0.041 (3)	0.050 (4)	−0.001 (3)	0.010 (3)	−0.006 (3)
C21	0.022 (2)	0.033 (3)	0.024 (2)	−0.003 (2)	0.0043 (19)	−0.004 (2)
C22	0.037 (3)	0.033 (3)	0.039 (3)	0.000 (2)	0.003 (2)	0.005 (2)
C23	0.033 (3)	0.058 (4)	0.050 (4)	0.009 (3)	0.001 (3)	0.004 (3)
C24	0.024 (3)	0.071 (5)	0.043 (3)	−0.007 (3)	0.001 (2)	−0.009 (3)
C25	0.044 (3)	0.043 (3)	0.047 (4)	−0.020 (3)	0.001 (3)	0.000 (3)
C26	0.028 (3)	0.031 (3)	0.039 (3)	−0.005 (2)	−0.004 (2)	0.006 (2)

Geometric parameters (Å, º) top

Au—S1	2.3086 (12)	C11—H11	0.9400
Au—P1	2.2508 (12)	C12—C13	1.386 (8)
Cl1—C3	1.746 (5)	C12—H12	0.9400
S1—C1	1.762 (5)	C13—C14	1.376 (8)
P1—C21	1.809 (5)	C13—H13	0.9400
P1—C15	1.815 (5)	C14—H14	0.9400
P1—C9	1.819 (5)	C15—C20	1.389 (7)
O1—C1	1.350 (6)	C15—C16	1.395 (7)
O1—C8	1.433 (6)	C16—C17	1.400 (8)
N1—C1	1.269 (6)	C16—H16	0.9400
N1—C2	1.414 (6)	C17—C18	1.371 (9)
C2—C7	1.383 (7)	C17—H17	0.9400
C2—C3	1.393 (7)	C18—C19	1.365 (9)
C3—C4	1.385 (7)	C18—H18	0.9400
C4—C5	1.365 (8)	C19—C20	1.396 (8)
C4—H4	0.9400	C19—H19	0.9400
C5—C6	1.372 (8)	C20—H20	0.9400
C5—H5	0.9400	C21—C26	1.380 (7)
C6—C7	1.380 (7)	C21—C22	1.393 (7)
C6—H6	0.9400	C22—C23	1.378 (8)
C7—H7	0.9400	C22—H22	0.9400
C8—H8A	0.9700	C23—C24	1.378 (9)
C8—H8B	0.9700	C23—H23	0.9400
C8—H8C	0.9700	C24—C25	1.372 (8)
C9—C14	1.390 (7)	C24—H24	0.9400
C9—C10	1.391 (7)	C25—C26	1.388 (7)
C10—C11	1.372 (7)	C25—H25	0.9400
C10—H10	0.9400	C26—H26	0.9400
C11—C12	1.376 (8)

P1—Au—S1	175.09 (5)	C11—C12—C13	119.3 (5)
C1—S1—Au	102.08 (17)	C11—C12—H12	120.4
C21—P1—C15	104.7 (2)	C13—C12—H12	120.4
C21—P1—C9	105.7 (2)	C14—C13—C12	120.5 (5)
C15—P1—C9	106.0 (2)	C14—C13—H13	119.7
C21—P1—Au	117.37 (16)	C12—C13—H13	119.7
C15—P1—Au	112.61 (16)	C13—C14—C9	119.9 (5)
C9—P1—Au	109.65 (16)	C13—C14—H14	120.1
C1—O1—C8	117.1 (4)	C9—C14—H14	120.1
C1—N1—C2	119.9 (4)	C20—C15—C16	119.4 (5)
N1—C1—O1	119.8 (4)	C20—C15—P1	118.1 (4)
N1—C1—S1	126.9 (4)	C16—C15—P1	122.5 (4)
O1—C1—S1	113.2 (3)	C15—C16—C17	118.8 (5)
C7—C2—C3	117.3 (5)	C15—C16—H16	120.6
C7—C2—N1	121.8 (5)	C17—C16—H16	120.6
C3—C2—N1	120.5 (5)	C18—C17—C16	121.4 (6)
C4—C3—C2	121.4 (5)	C18—C17—H17	119.3
C4—C3—Cl1	118.5 (4)	C16—C17—H17	119.3
C2—C3—Cl1	120.1 (4)	C19—C18—C17	119.6 (6)
C5—C4—C3	120.3 (5)	C19—C18—H18	120.2
C5—C4—H4	119.9	C17—C18—H18	120.2
C3—C4—H4	119.9	C18—C19—C20	120.6 (6)
C4—C5—C6	119.0 (5)	C18—C19—H19	119.7
C4—C5—H5	120.5	C20—C19—H19	119.7
C6—C5—H5	120.5	C15—C20—C19	120.2 (6)
C5—C6—C7	121.3 (5)	C15—C20—H20	119.9
C5—C6—H6	119.3	C19—C20—H20	119.9
C7—C6—H6	119.3	C26—C21—C22	119.6 (5)
C6—C7—C2	120.7 (5)	C26—C21—P1	122.4 (4)
C6—C7—H7	119.7	C22—C21—P1	118.1 (4)
C2—C7—H7	119.7	C23—C22—C21	119.4 (5)
O1—C8—H8A	109.5	C23—C22—H22	120.3
O1—C8—H8B	109.5	C21—C22—H22	120.3
H8A—C8—H8B	109.5	C22—C23—C24	120.9 (6)
O1—C8—H8C	109.5	C22—C23—H23	119.5
H8A—C8—H8C	109.5	C24—C23—H23	119.5
H8B—C8—H8C	109.5	C25—C24—C23	119.9 (5)
C14—C9—C10	119.4 (5)	C25—C24—H24	120.1
C14—C9—P1	121.9 (4)	C23—C24—H24	120.1
C10—C9—P1	118.7 (4)	C24—C25—C26	119.9 (5)
C11—C10—C9	119.9 (5)	C24—C25—H25	120.1
C11—C10—H10	120.1	C26—C25—H25	120.1
C9—C10—H10	120.1	C21—C26—C25	120.4 (5)
C10—C11—C12	120.9 (5)	C21—C26—H26	119.8
C10—C11—H11	119.5	C25—C26—H26	119.8
C12—C11—H11	119.5

C2—N1—C1—O1	−173.1 (4)	C10—C9—C14—C13	−1.8 (8)
C2—N1—C1—S1	10.0 (7)	P1—C9—C14—C13	177.5 (4)
C8—O1—C1—N1	2.5 (7)	C21—P1—C15—C20	74.9 (4)
C8—O1—C1—S1	179.8 (4)	C9—P1—C15—C20	−173.6 (4)
Au—S1—C1—N1	174.2 (4)	Au—P1—C15—C20	−53.7 (4)
Au—S1—C1—O1	−2.9 (4)	C21—P1—C15—C16	−104.3 (4)
C1—N1—C2—C7	60.3 (7)	C9—P1—C15—C16	7.2 (5)
C1—N1—C2—C3	−126.3 (5)	Au—P1—C15—C16	127.1 (4)
C7—C2—C3—C4	−1.1 (7)	C20—C15—C16—C17	−0.7 (8)
N1—C2—C3—C4	−174.9 (5)	P1—C15—C16—C17	178.4 (4)
C7—C2—C3—Cl1	179.8 (4)	C15—C16—C17—C18	0.1 (9)
N1—C2—C3—Cl1	6.1 (7)	C16—C17—C18—C19	0.6 (10)
C2—C3—C4—C5	0.1 (8)	C17—C18—C19—C20	−0.7 (10)
Cl1—C3—C4—C5	179.2 (4)	C16—C15—C20—C19	0.6 (8)
C3—C4—C5—C6	0.0 (9)	P1—C15—C20—C19	−178.6 (4)
C4—C5—C6—C7	1.0 (9)	C18—C19—C20—C15	0.1 (9)
C5—C6—C7—C2	−2.0 (9)	C15—P1—C21—C26	9.0 (5)
C3—C2—C7—C6	2.1 (8)	C9—P1—C21—C26	−102.7 (4)
N1—C2—C7—C6	175.7 (5)	Au—P1—C21—C26	134.7 (4)
C21—P1—C9—C14	22.3 (5)	C15—P1—C21—C22	−172.6 (4)
C15—P1—C9—C14	−88.5 (5)	C9—P1—C21—C22	75.7 (4)
Au—P1—C9—C14	149.7 (4)	Au—P1—C21—C22	−46.9 (4)
C21—P1—C9—C10	−158.4 (4)	C26—C21—C22—C23	1.7 (8)
C15—P1—C9—C10	90.8 (4)	P1—C21—C22—C23	−176.7 (4)
Au—P1—C9—C10	−31.0 (5)	C21—C22—C23—C24	−1.8 (9)
C14—C9—C10—C11	3.2 (8)	C22—C23—C24—C25	0.8 (9)
P1—C9—C10—C11	−176.1 (4)	C23—C24—C25—C26	0.3 (9)
C9—C10—C11—C12	−1.8 (9)	C22—C21—C26—C25	−0.6 (8)
C10—C11—C12—C13	−0.9 (9)	P1—C21—C26—C25	177.7 (4)
C11—C12—C13—C14	2.3 (9)	C24—C25—C26—C21	−0.3 (8)
C12—C13—C14—C9	−0.9 (9)

Experimental details

Crystal data
Chemical formula	[Au(C₈H₇ClNOS)(C₁₈H₁₅P)]
M_r	659.89
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	223
a, b, c (Å)	8.9388 (5), 26.2804 (15), 10.3233 (6)
β (°)	96.599 (1)
V (Å³)	2409.0 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	6.39
Crystal size (mm)	0.13 × 0.10 × 0.07

Data collection
Diffractometer	Bruker SMART CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2000)
T_min, T_max	0.521, 1
No. of measured, independent and observed [I > 2σ(I)] reflections	17015, 5537, 4400
R_int	0.047
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.032, 0.085, 1.04
No. of reflections	5537
No. of parameters	290
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.17, −0.54

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

Selected bond lengths (Å) top

Au—S1

2.3086 (12)

Au—P1

2.2508 (12)

Acknowledgements

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

References

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