[(Z)-N-(4-Chloro­phen­yl)-O-methyl­thio­carbamato-κS](triphenyl­phosphine-κP)gold(I)

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

doi:10.1107/S1600536809050454

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 12| December 2009| Page m1700

doi:10.1107/S1600536809050454

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[(Z)-N-(4-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 15 November 2009; accepted 24 November 2009; online 28 November 2009)

The title compound, [Au(C₈H₇ClNOS)(C₁₈H₁₅P)], 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 interactions.

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 = 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[F² > 2σ(F²)] = 0.029
wR(F²) = 0.090
S = 1.06
5570 reflections
290 parameters
H-atom parameters constrained
Δρ_max = 1.17 e Å⁻³
Δρ_min = −0.62 e Å⁻³

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) -x, -y, -z+1.

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 ).

Supporting information

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

Structure factors: contains datablock I. DOI: 10.1107/S1600536809050454/hy2256Isup2.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)₃P]Au[SC(OMe)N(C₆H₄Cl-p)], was synthesized.

The thiocarbamide functions as a thiolate ligand as seen in the magnitudes of the C1—S1 and C1—N1 bond distances of 1.756 (5) and 1.271 (6) Å, respectively; the conformation about C1—N1 is Z. While the central SC(O)N chromophore is planar as seen in the S1—C1—N1—C2 and O1—C1—N1—C2 torsion angles of -0.8 (7) and -179.0 (4)°, respectively, the N-bound aryl ring is orthogonal to this plane as seen in the C1–N1–C2–C3 torsion angle of -76.6 (6)°. The thiocarbamide and phosphine ligands define an S, P donor set (Table 1 and Fig. 1). The deviation of the S1—Au—P1 angle [175.14 (5)°] from linearity is traced to the close approach of the O1 atom to the Au atom [2.882 (3) Å]. In the crystal structure, centrosymmetrically related molecules associate via C—H···O interactions (Table 2 and Fig. 2). The dimeric units formed are consolidated into the crystal structure by C—H···π interactions. The closest such contact occurs between C24—H24 and the ring centroid (Cg) of (C15—C20)ⁱ [C24···Cgⁱ = 3.552 (6), H24···Cgⁱ = 2.73 Å, C24—H24···Cgⁱ = 146°, symmetry code: (i) -1+x, y, 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 MeOC(S)N(H)(C₆H₄Cl-p) in the presence of base (Hall et al., 1993).

Computing details top

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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).

Figures top

	Fig. 1. Molecular structure of the title compound. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. Supramolecular dimer in the title compound, mediated by C—H···O contacts (orange dashed lines). [Colour codes: Au orange; Cl cyan; S yellow; P pink; O red; N blue; C grey; and H green.]

[(Z)-N-(4-Chlorophenyl)-O-methylthiocarbamato- κS](triphenylphosphine-κP)gold(I) top

Crystal data top

[Au(C₈H₇ClNOS)(C₁₈H₁₅P)]	F(000) = 1280
M_r = 659.89	D_x = 1.804 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

Data collection top

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

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)] = 0.029	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.090	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0462P)²P] where P = (F_o² + 2F_c²)/3
5570 reflections	(Δ/σ)_max = 0.001
290 parameters	Δρ_max = 1.17 e Å⁻³
0 restraints	Δρ_min = −0.62 e Å⁻³

Crystal data top

[Au(C₈H₇ClNOS)(C₁₈H₁₅P)]	V = 2429.3 (3) Å³
M_r = 659.89	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 9.1781 (6) Å	µ = 6.34 mm⁻¹
b = 17.5679 (12) Å	T = 223 K
c = 15.5384 (11) Å	0.11 × 0.10 × 0.07 mm
β = 104.156 (2)°

Data collection top

Bruker SMART APEX CCD diffractometer	5570 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	4526 reflections with I > 2σ(I)
T_min = 0.363, T_max = 1.000	R_int = 0.042
17091 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.029	0 restraints
wR(F²) = 0.090	H-atom parameters constrained
S = 1.06	Δρ_max = 1.17 e Å⁻³
5570 reflections	Δρ_min = −0.62 e Å⁻³
290 parameters

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

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) −x, −y, −z+1.

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)	9.1781 (6), 17.5679 (12), 15.5384 (11)
β (°)	104.156 (2)
V (Å³)	2429.3 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	6.34
Crystal size (mm)	0.11 × 0.10 × 0.07

Data collection
Diffractometer	Bruker SMART APEX CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.363, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	17091, 5570, 4526
R_int	0.042
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.029, 0.090, 1.06
No. of reflections	5570
No. of parameters	290
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.17, −0.62

Computer programs: SMART (Bruker, 2007), SAINT (Bruker, 2007), PATTY in DIRDIF92 (Beurskens et al., 1992), SHELXL97 (Sheldrick, 2008), DIAMOND (Brandenburg, 1999), publCIF (Westrip, 2009).

Selected bond lengths (Å) top

Au—S1

2.3018 (12)

Au—P1

2.2473 (12)

Hydrogen-bond geometry (Å, º) top

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) −x, −y, −z+1.

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. (1999). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2007). SMART and SAINT. 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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Volume 65| Part 12| December 2009| Page m1700

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metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

[(Z)-N-(4-Chloro­phen­yl)-O-methyl­thio­carbamato-κS](tri­phenyl­phosphine-κP)gold(I)

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

metal-organic compounds

[(Z)-N-(4-Chlorophenyl)-O-methylthiocarbamato-κS](triphenylphosphine-κP)gold(I)