[(Z)-O-Methyl N-(3-chloro­phen­yl)thio­carbamato-κS](triphenyl­phosphine-κP)gold(I)

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

doi:10.1107/S1600536810017319

[(Z)-O-Methyl N-(3-chlorophenyl)thiocarbamato-κS](triphenylphosphine-κP)gold(I)

The Au atom in the title compound, [Au(C₈H₇ClNOS)(C₁₈H₁₅P)], exists within a slightly distorted linear geometry defined by an S,P-donor set [S—Au—P angle = 174.61 (4)°], with the distortion related to a short intramolecular Au

O contact [2.988 (3) Å]. In the crystal structure, molecules are arranged into supramolecular chains along the b axis by C—H

π interactions.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536810017319/lh5042sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536810017319/lh5042Isup2.hkl Contains datablock I

CCDC reference: 781215

checkCIF report

Key indicators

Single-crystal X-ray study
T = 223 K
Mean (C-C) = 0.008 Å
R factor = 0.032
wR factor = 0.089
Data-to-parameter ratio = 19.1

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT919_ALERT_3_B Reflection(s) # Likely Affected by the Beamstop           1

Alert level C
SHFSU01_ALERT_2_C  Test not performed. _refine_ls_shift/su_max and
            _refine_ls_shift/esd_max not present.
            Absolute value of the parameter shift to su ratio given   0.001
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C12    --  C13     ..       5.80 su
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         S1
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.600         27
PLAT912_ALERT_4_C Missing # of FCF Reflections Above STh/L=  0.600         22

Alert level G
PLAT710_ALERT_4_G Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #          1
            P1  -AU  -S1  -C1     -8.40  0.70   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_G Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #          2
            S1  -AU  -P1  -C21  -104.70  0.70   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_G Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #          3
            S1  -AU  -P1  -C9     13.30  0.70   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_G Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #          4
            S1  -AU  -P1  -C15   131.80  0.70   1.555   1.555   1.555   1.555

   0 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
   5 ALERT level C = Check and explain
   4 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   3 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   5 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Comment top

The remarkable propensity of molecules with the general formula R₃PAu[SC(OR')═ NR''], for R, R' and R'' = alkyl and aryl, to provide diffraction quality crystals have proved useful for systematic crystal engineering studies (Ho et al., 2006; Ho & Tiekink, 2007; Kuan et al., 2008). The structure of the title compound, (I), was investigated in the context of the above.

The nearly linear SP coordination geometry observed for the Au atom in (I), Fig. 1, is defined by phosphine and thiolate ligands, Table 1. The deviation from the ideal linearity [S—Au—P = 174.61 (4) °] is related to a short intramolecular Au···O contact [2.988 (3) Å]. With the exception of the p-tolyl derivatives (Kuan et al., 2008), the overall molecular conformation (including close Au···.O contacts) conforms to the majority of related compounds having monodentate phosphine ligands.

The major feature of the crystal packing is the presence of C–H···π interactions that lead to the formation of supramolecular chains along the b axis, Fig. 2 and Table 2. Notably, the Cl-substituted benzene ring accepts two such interactions also donates one. Chains are arranged into layers in the (1 0 1) plane, Fig. 3.

Related literature top

For the 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-3) in the presence of NaOH (Hall et al., 1993). Crystals were obtained by the slow evaporation of a CHCl₃/hexane (3/1) solution held at room temperature.

Structure description top

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (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: ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

	Fig. 1. Molecular structure of (I) showing atom-labelling scheme and displacement ellipsoids at the 50% probability level.
	Fig. 2. A supramolecular chain along the b axis, highlighting the pivotal role played by the N-bound benzene ring in the formation of donor and acceptor C–H···π interactions
	Fig. 3. A view in projection along the b axis of the crystal packing in (I), highlighting the stacking of layers mediated by the C–H···π contacts (shown as purple dashed lines).

[(Z)-O-Methyl N-(3-chlorophenyl)thiocarbamato- κS](triphenylphosphine-κP)gold(I) top

Crystal data top

[Au(C₈H₇ClNOS)(C₁₈H₁₅P)]	Z = 2
M_r = 659.89	F(000) = 640
Triclinic, P1	D_x = 1.805 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71069 Å
a = 10.4236 (8) Å	Cell parameters from 6911 reflections
b = 10.6961 (8) Å	θ = 1.8–30.1°
c = 12.7439 (9) Å	µ = 6.34 mm⁻¹
α = 72.724 (2)°	T = 223 K
β = 66.105 (1)°	Block, colourless
γ = 72.530 (2)°	0.19 × 0.08 × 0.05 mm
V = 1213.83 (16) Å³

Data collection top

Bruker SMART CCD diffractometer	5525 independent reflections
Radiation source: fine-focus sealed tube	4787 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.023
ω scans	θ_max = 27.5°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −11→13
T_min = 0.515, T_max = 1	k = −13→13
8630 measured reflections	l = −15→16

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) = 0.089	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0473P)²] where P = (F_o² + 2F_c²)/3
5525 reflections	(Δ/σ)_max < 0.001
290 parameters	Δρ_max = 1.16 e Å⁻³
0 restraints	Δρ_min = −1.21 e Å⁻³

Crystal data top

[Au(C₈H₇ClNOS)(C₁₈H₁₅P)]	γ = 72.530 (2)°
M_r = 659.89	V = 1213.83 (16) Å³
Triclinic, P1	Z = 2
a = 10.4236 (8) Å	Mo Kα radiation
b = 10.6961 (8) Å	µ = 6.34 mm⁻¹
c = 12.7439 (9) Å	T = 223 K
α = 72.724 (2)°	0.19 × 0.08 × 0.05 mm
β = 66.105 (1)°

Data collection top

Bruker SMART CCD diffractometer	5525 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2000)	4787 reflections with I > 2σ(I)
T_min = 0.515, T_max = 1	R_int = 0.023
8630 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.032	0 restraints
wR(F²) = 0.089	H-atom parameters constrained
S = 1.05	Δρ_max = 1.16 e Å⁻³
5525 reflections	Δρ_min = −1.21 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	0.11162 (2)	0.105503 (16)	0.249566 (14)	0.03318 (8)
Cl1	0.29679 (17)	−0.34461 (14)	−0.25655 (13)	0.0480 (3)
S1	0.1802 (2)	−0.03071 (14)	0.11917 (12)	0.0569 (5)
P1	0.05527 (13)	0.25261 (11)	0.36314 (10)	0.0234 (2)
O1	0.2184 (4)	0.2044 (3)	−0.0097 (3)	0.0418 (9)
N1	0.3288 (5)	0.0379 (4)	−0.1105 (3)	0.0349 (9)
C1	0.2538 (6)	0.0735 (5)	−0.0159 (4)	0.0341 (11)
C2	0.3735 (5)	−0.0998 (5)	−0.1156 (4)	0.0316 (10)
C3	0.3166 (5)	−0.1501 (5)	−0.1734 (4)	0.0314 (10)
H3	0.2451	−0.0950	−0.2035	0.038*
C4	0.3677 (5)	−0.2828 (5)	−0.1855 (4)	0.0317 (10)
C5	0.4734 (6)	−0.3662 (5)	−0.1412 (4)	0.0371 (12)
H5	0.5049	−0.4566	−0.1474	0.045*
C6	0.5304 (6)	−0.3132 (6)	−0.0882 (5)	0.0409 (12)
H6	0.6033	−0.3676	−0.0594	0.049*
C7	0.4820 (6)	−0.1809 (5)	−0.0766 (4)	0.0363 (11)
H7	0.5239	−0.1460	−0.0416	0.044*
C8	0.2819 (8)	0.2932 (5)	−0.1111 (5)	0.0521 (15)
H8A	0.3855	0.2663	−0.1339	0.078*
H8B	0.2515	0.3829	−0.0956	0.078*
H8C	0.2528	0.2917	−0.1739	0.078*
C9	0.0939 (5)	0.4105 (4)	0.2678 (4)	0.0234 (9)
C10	0.0614 (5)	0.4495 (5)	0.1642 (4)	0.0304 (10)
H10	0.0210	0.3945	0.1462	0.037*
C11	0.0890 (6)	0.5678 (5)	0.0901 (5)	0.0399 (12)
H11	0.0651	0.5949	0.0219	0.048*
C12	0.1513 (6)	0.6478 (5)	0.1140 (4)	0.0343 (11)
H12	0.1703	0.7286	0.0618	0.041*
C13	0.1852 (5)	0.6108 (5)	0.2118 (5)	0.0371 (12)
H13	0.2286	0.6656	0.2271	0.044*
C14	0.1562 (5)	0.4911 (4)	0.2909 (4)	0.0282 (10)
H14	0.1791	0.4661	0.3594	0.034*
C15	−0.1311 (5)	0.2901 (5)	0.4571 (4)	0.0275 (10)
C16	−0.2001 (6)	0.1849 (6)	0.5219 (5)	0.0405 (12)
H16	−0.1521	0.0965	0.5143	0.049*
C17	−0.3406 (6)	0.2107 (7)	0.5980 (5)	0.0540 (17)
H17	−0.3868	0.1393	0.6437	0.065*
C18	−0.4121 (6)	0.3393 (7)	0.6068 (5)	0.0527 (16)
H18	−0.5081	0.3558	0.6569	0.063*
C19	−0.3451 (6)	0.4442 (6)	0.5434 (5)	0.0435 (13)
H19	−0.3942	0.5322	0.5512	0.052*
C20	−0.2039 (5)	0.4195 (5)	0.4673 (4)	0.0334 (11)
H20	−0.1580	0.4913	0.4227	0.040*
C21	0.1557 (5)	0.2115 (4)	0.4603 (4)	0.0239 (9)
C22	0.3060 (5)	0.1834 (5)	0.4125 (4)	0.0351 (11)
H22	0.3522	0.1829	0.3321	0.042*
C23	0.3858 (6)	0.1567 (5)	0.4825 (5)	0.0407 (12)
H23	0.4864	0.1408	0.4497	0.049*
C24	0.3169 (6)	0.1532 (5)	0.6035 (5)	0.0387 (12)
H24	0.3716	0.1345	0.6517	0.046*
C25	0.1711 (6)	0.1769 (6)	0.6509 (4)	0.0398 (12)
H25	0.1257	0.1725	0.7320	0.048*
C26	0.0902 (5)	0.2070 (5)	0.5816 (4)	0.0340 (11)
H26	−0.0104	0.2250	0.6153	0.041*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Au	0.05238 (14)	0.02569 (11)	0.02024 (10)	−0.01321 (8)	−0.00694 (8)	−0.00573 (7)
Cl1	0.0597 (9)	0.0487 (8)	0.0462 (8)	−0.0174 (7)	−0.0213 (7)	−0.0137 (6)
S1	0.1055 (13)	0.0342 (7)	0.0234 (6)	−0.0339 (8)	0.0019 (7)	−0.0102 (5)
P1	0.0305 (6)	0.0229 (5)	0.0167 (5)	−0.0074 (5)	−0.0073 (4)	−0.0035 (4)
O1	0.069 (3)	0.0284 (17)	0.0234 (17)	−0.0170 (17)	−0.0080 (17)	−0.0037 (14)
N1	0.044 (2)	0.037 (2)	0.021 (2)	−0.0117 (19)	−0.0066 (18)	−0.0065 (17)
C1	0.050 (3)	0.033 (2)	0.023 (2)	−0.018 (2)	−0.009 (2)	−0.0052 (19)
C2	0.034 (3)	0.039 (3)	0.019 (2)	−0.009 (2)	−0.0034 (19)	−0.0090 (19)
C3	0.034 (3)	0.034 (2)	0.022 (2)	−0.005 (2)	−0.0081 (19)	−0.0022 (19)
C4	0.033 (3)	0.042 (3)	0.020 (2)	−0.012 (2)	−0.0041 (19)	−0.010 (2)
C5	0.036 (3)	0.034 (3)	0.031 (3)	−0.002 (2)	−0.006 (2)	−0.007 (2)
C6	0.033 (3)	0.052 (3)	0.030 (3)	−0.001 (2)	−0.010 (2)	−0.006 (2)
C7	0.039 (3)	0.047 (3)	0.024 (2)	−0.009 (2)	−0.013 (2)	−0.007 (2)
C8	0.074 (4)	0.036 (3)	0.039 (3)	−0.017 (3)	−0.015 (3)	0.002 (2)
C9	0.022 (2)	0.023 (2)	0.023 (2)	−0.0053 (17)	−0.0038 (17)	−0.0068 (17)
C10	0.047 (3)	0.030 (2)	0.021 (2)	−0.016 (2)	−0.018 (2)	0.0012 (18)
C11	0.054 (3)	0.038 (3)	0.027 (3)	−0.009 (2)	−0.017 (2)	−0.002 (2)
C12	0.047 (3)	0.025 (2)	0.022 (2)	−0.012 (2)	−0.003 (2)	−0.0001 (18)
C13	0.032 (3)	0.029 (2)	0.047 (3)	−0.010 (2)	−0.003 (2)	−0.015 (2)
C14	0.039 (3)	0.028 (2)	0.023 (2)	−0.007 (2)	−0.014 (2)	−0.0072 (18)
C15	0.029 (2)	0.035 (2)	0.025 (2)	−0.0115 (19)	−0.0122 (19)	−0.0060 (19)
C16	0.041 (3)	0.042 (3)	0.038 (3)	−0.017 (2)	−0.018 (2)	0.008 (2)
C17	0.039 (3)	0.072 (4)	0.047 (3)	−0.034 (3)	−0.017 (3)	0.021 (3)
C18	0.026 (3)	0.087 (5)	0.036 (3)	−0.008 (3)	−0.005 (2)	−0.010 (3)
C19	0.036 (3)	0.062 (4)	0.034 (3)	−0.006 (3)	−0.011 (2)	−0.017 (3)
C20	0.030 (3)	0.041 (3)	0.032 (3)	−0.008 (2)	−0.011 (2)	−0.011 (2)
C21	0.030 (2)	0.022 (2)	0.018 (2)	−0.0034 (17)	−0.0083 (17)	−0.0027 (16)
C22	0.034 (3)	0.039 (3)	0.022 (2)	−0.004 (2)	−0.007 (2)	0.000 (2)
C23	0.030 (3)	0.044 (3)	0.036 (3)	−0.002 (2)	−0.012 (2)	0.004 (2)
C24	0.038 (3)	0.048 (3)	0.031 (3)	−0.008 (2)	−0.019 (2)	0.001 (2)
C25	0.039 (3)	0.058 (3)	0.021 (2)	−0.009 (3)	−0.010 (2)	−0.007 (2)
C26	0.026 (2)	0.042 (3)	0.028 (2)	−0.003 (2)	−0.004 (2)	−0.010 (2)

Geometric parameters (Å, º) top

Au—P1	2.2416 (11)	C11—H11	0.9400
Au—S1	2.2902 (13)	C12—C13	1.348 (8)
Cl1—C4	1.731 (5)	C12—H12	0.9400
S1—C1	1.760 (5)	C13—C14	1.402 (6)
P1—C21	1.809 (5)	C13—H13	0.9400
P1—C9	1.813 (4)	C14—H14	0.9400
P1—C15	1.817 (5)	C15—C20	1.380 (7)
O1—C1	1.355 (6)	C15—C16	1.385 (6)
O1—C8	1.401 (6)	C16—C17	1.388 (8)
N1—C1	1.241 (6)	C16—H16	0.9400
N1—C2	1.418 (6)	C17—C18	1.367 (9)
C2—C7	1.374 (7)	C17—H17	0.9400
C2—C3	1.402 (7)	C18—C19	1.369 (8)
C3—C4	1.390 (7)	C18—H18	0.9400
C3—H3	0.9400	C19—C20	1.393 (7)
C4—C5	1.394 (7)	C19—H19	0.9400
C5—C6	1.372 (8)	C20—H20	0.9400
C5—H5	0.9400	C21—C22	1.404 (7)
C6—C7	1.384 (7)	C21—C26	1.406 (6)
C6—H6	0.9400	C22—C23	1.368 (8)
C7—H7	0.9400	C22—H22	0.9400
C8—H8A	0.9700	C23—C24	1.407 (7)
C8—H8B	0.9700	C23—H23	0.9400
C8—H8C	0.9700	C24—C25	1.362 (7)
C9—C14	1.375 (6)	C24—H24	0.9400
C9—C10	1.408 (6)	C25—C26	1.366 (7)
C10—C11	1.365 (7)	C25—H25	0.9400
C10—H10	0.9400	C26—H26	0.9400
C11—C12	1.376 (7)

P1—Au—S1	174.61 (4)	C13—C12—C11	120.3 (5)
C1—S1—Au	102.46 (16)	C13—C12—H12	119.8
C21—P1—C9	105.6 (2)	C11—C12—H12	119.8
C21—P1—C15	104.4 (2)	C12—C13—C14	120.4 (5)
C9—P1—C15	105.7 (2)	C12—C13—H13	119.8
C21—P1—Au	115.81 (14)	C14—C13—H13	119.8
C9—P1—Au	107.75 (14)	C9—C14—C13	119.7 (4)
C15—P1—Au	116.62 (15)	C9—C14—H14	120.1
C1—O1—C8	116.8 (4)	C13—C14—H14	120.1
C1—N1—C2	120.4 (4)	C20—C15—C16	119.6 (5)
N1—C1—O1	120.4 (4)	C20—C15—P1	121.9 (4)
N1—C1—S1	126.6 (4)	C16—C15—P1	118.6 (4)
O1—C1—S1	113.0 (3)	C15—C16—C17	119.6 (5)
C7—C2—C3	119.4 (5)	C15—C16—H16	120.2
C7—C2—N1	121.4 (5)	C17—C16—H16	120.2
C3—C2—N1	118.8 (5)	C18—C17—C16	120.4 (5)
C4—C3—C2	118.9 (5)	C18—C17—H17	119.8
C4—C3—H3	120.6	C16—C17—H17	119.8
C2—C3—H3	120.6	C17—C18—C19	120.6 (5)
C3—C4—C5	121.4 (5)	C17—C18—H18	119.7
C3—C4—Cl1	118.7 (4)	C19—C18—H18	119.7
C5—C4—Cl1	119.9 (4)	C18—C19—C20	119.6 (5)
C6—C5—C4	118.5 (5)	C18—C19—H19	120.2
C6—C5—H5	120.8	C20—C19—H19	120.2
C4—C5—H5	120.8	C15—C20—C19	120.3 (5)
C5—C6—C7	120.9 (5)	C15—C20—H20	119.9
C5—C6—H6	119.6	C19—C20—H20	119.9
C7—C6—H6	119.6	C22—C21—C26	118.3 (4)
C2—C7—C6	120.9 (5)	C22—C21—P1	118.6 (3)
C2—C7—H7	119.6	C26—C21—P1	123.1 (4)
C6—C7—H7	119.6	C23—C22—C21	120.3 (5)
O1—C8—H8A	109.5	C23—C22—H22	119.8
O1—C8—H8B	109.5	C21—C22—H22	119.8
H8A—C8—H8B	109.5	C22—C23—C24	119.9 (5)
O1—C8—H8C	109.5	C22—C23—H23	120.0
H8A—C8—H8C	109.5	C24—C23—H23	120.0
H8B—C8—H8C	109.5	C25—C24—C23	120.0 (5)
C14—C9—C10	119.2 (4)	C25—C24—H24	120.0
C14—C9—P1	123.0 (4)	C23—C24—H24	120.0
C10—C9—P1	117.8 (3)	C24—C25—C26	120.7 (5)
C11—C10—C9	119.5 (4)	C24—C25—H25	119.7
C11—C10—H10	120.2	C26—C25—H25	119.7
C9—C10—H10	120.2	C25—C26—C21	120.7 (5)
C10—C11—C12	120.8 (5)	C25—C26—H26	119.6
C10—C11—H11	119.6	C21—C26—H26	119.6
C12—C11—H11	119.6

P1—Au—S1—C1	−8.4 (7)	C11—C12—C13—C14	−0.6 (8)
S1—Au—P1—C21	−104.7 (7)	C10—C9—C14—C13	0.5 (7)
S1—Au—P1—C9	13.3 (7)	P1—C9—C14—C13	178.8 (3)
S1—Au—P1—C15	131.8 (7)	C12—C13—C14—C9	0.6 (7)
C2—N1—C1—O1	175.9 (5)	C21—P1—C15—C20	95.9 (4)
C2—N1—C1—S1	−5.4 (8)	C9—P1—C15—C20	−15.2 (5)
C8—O1—C1—N1	−6.2 (8)	Au—P1—C15—C20	−134.9 (4)
C8—O1—C1—S1	175.0 (4)	C21—P1—C15—C16	−82.6 (4)
Au—S1—C1—N1	166.0 (5)	C9—P1—C15—C16	166.2 (4)
Au—S1—C1—O1	−15.3 (4)	Au—P1—C15—C16	46.6 (4)
C1—N1—C2—C7	−75.8 (7)	C20—C15—C16—C17	−1.3 (8)
C1—N1—C2—C3	111.4 (6)	P1—C15—C16—C17	177.3 (4)
C7—C2—C3—C4	2.6 (7)	C15—C16—C17—C18	1.8 (9)
N1—C2—C3—C4	175.6 (4)	C16—C17—C18—C19	−1.9 (10)
C2—C3—C4—C5	0.2 (7)	C17—C18—C19—C20	1.5 (9)
C2—C3—C4—Cl1	179.8 (3)	C16—C15—C20—C19	0.9 (8)
C3—C4—C5—C6	−2.2 (7)	P1—C15—C20—C19	−177.6 (4)
Cl1—C4—C5—C6	178.2 (4)	C18—C19—C20—C15	−1.0 (8)
C4—C5—C6—C7	1.4 (8)	C9—P1—C21—C22	−65.8 (4)
C3—C2—C7—C6	−3.4 (7)	C15—P1—C21—C22	−177.0 (4)
N1—C2—C7—C6	−176.2 (5)	Au—P1—C21—C22	53.3 (4)
C5—C6—C7—C2	1.4 (8)	C9—P1—C21—C26	113.8 (4)
C21—P1—C9—C14	−14.8 (4)	C15—P1—C21—C26	2.6 (4)
C15—P1—C9—C14	95.5 (4)	Au—P1—C21—C26	−127.1 (4)
Au—P1—C9—C14	−139.1 (3)	C26—C21—C22—C23	−2.0 (7)
C21—P1—C9—C10	163.6 (4)	P1—C21—C22—C23	177.6 (4)
C15—P1—C9—C10	−86.1 (4)	C21—C22—C23—C24	2.0 (8)
Au—P1—C9—C10	39.2 (4)	C22—C23—C24—C25	−0.3 (9)
C14—C9—C10—C11	−1.5 (7)	C23—C24—C25—C26	−1.4 (9)
P1—C9—C10—C11	−180.0 (4)	C24—C25—C26—C21	1.4 (8)
C9—C10—C11—C12	1.6 (8)	C22—C21—C26—C25	0.4 (7)
C10—C11—C12—C13	−0.5 (8)	P1—C21—C26—C25	−179.2 (4)

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are the centroids of the C2–C7 and C9–C14 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12···Cg1ⁱ	0.94	2.82	3.472 (6)	127
C22—H22···Cg1ⁱⁱ	0.94	2.72	3.565 (5)	149
C6—H6···Cg2ⁱⁱ	0.94	2.97	3.615 (7)	127

Symmetry codes: (i) x, y+1, z; (ii) −x+1, −y, −z.

Experimental details

Crystal data
Chemical formula	[Au(C₈H₇ClNOS)(C₁₈H₁₅P)]
M_r	659.89
Crystal system, space group	Triclinic, P1
Temperature (K)	223
a, b, c (Å)	10.4236 (8), 10.6961 (8), 12.7439 (9)
α, β, γ (°)	72.724 (2), 66.105 (1), 72.530 (2)
V (Å³)	1213.83 (16)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	6.34
Crystal size (mm)	0.19 × 0.08 × 0.05

Data collection
Diffractometer	Bruker SMART CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2000)
T_min, T_max	0.515, 1
No. of measured, independent and observed [I > 2σ(I)] reflections	8630, 5525, 4787
R_int	0.023
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.032, 0.089, 1.05
No. of reflections	5525
No. of parameters	290
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.16, −1.21

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), PATTY in DIRDIF92 (Beurskens et al., 1992), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006), publCIF (Westrip, 2010).