[(Z)-O-Methyl-N-propyl-thio-carbamato-κS](triphenyl-phosphine-κP)gold(I).

In the title compound, [Au(C(5)H(10)NOS)(C(18)H(15)P)], the Au(I) atom is linearly coordinated within an S,P-donor set with distortion from an ideal linear geometry [S-Au-P = 176.71 (6)°] due to an intra-molecular Au⋯O contact [2.943 (4) Å]. In the crystal structure, centrosymmetrically related mol-ecules associate via C-H⋯O inter-actions.

Related literature

For structural systematics and luminescence properties of pan class="Chemical">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

[pan class="Chemical">Au(C5H10NOS)(C18H15P)]

M = 591.44

Monoclinic,

a = 13.9852 (16) Å

b = 11.1592 (13) Å

c = 15.0975 (17) Å

β = 107.605 (2)°

V = 2245.8 (4) Å3

Z = 4

Mo Kα radiation

μ = 6.73 mm−1

T = 223 K

0.26 × 0.13 × 0.01 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T min = 0.376, T max = 1

15397 measured reflections

5165 independent reflections

4702 reflections with I > 2σ(I)

R int = 0.047

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.106

S = 1.20

5165 reflections

254 parameters

H-atom parameters constrained

Δρmax = 1.41 e Å−3

Δρmin = −2.23 e Å−3

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); data reduction: SAINT; program(s) used to solve structure: pan class="Chemical">PATTY in DIRDIF92 (Beurskens et al., 1992 ▶); class="Chemical">program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graclass="Chemical">phics: DIAMOND (Brandenburg, 2006 ▶); software used to class="Chemical">preclass="Chemical">pare material for class="Chemical">publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809046856/hg2583sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809046856/hg2583Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

[Au(C5H10NOS)(C18H15P)]	F(000) = 1152
Mr = 591.44	Dx = 1.749 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71069 Å
Hall symbol: -P 2yn	Cell parameters from 953 reflections
a = 13.9852 (16) Å	θ = 2.3–29.6°
b = 11.1592 (13) Å	µ = 6.73 mm−1
c = 15.0975 (17) Å	T = 223 K
β = 107.605 (2)°	Plate, colourless
V = 2245.8 (4) Å3	0.26 × 0.13 × 0.01 mm
Z = 4

Bruker SMART CCD diffractometer	5165 independent reflections
Radiation source: fine-focus sealed tube	4702 reflections with I > 2σ(I)
graphite	Rint = 0.047
ω scans	θmax = 27.5°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −18→18
Tmin = 0.376, Tmax = 1	k = −14→8
15397 measured reflections	l = −19→17

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.106	H-atom parameters constrained
S = 1.20	w = 1/[σ2(Fo2) + (0.0416P)2 + 1.6273P] where P = (Fo2 + 2Fc2)/3
5165 reflections	(Δ/σ)max = 0.001
254 parameters	Δρmax = 1.41 e Å−3
0 restraints	Δρmin = −2.23 e Å−3

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.

	x	y	z	Uiso*/Ueq
Au	0.260547 (17)	0.07193 (2)	0.417669 (15)	0.03002 (9)
S1	0.15590 (13)	−0.09274 (15)	0.39447 (11)	0.0358 (4)
P1	0.35886 (12)	0.23644 (14)	0.44661 (10)	0.0289 (3)
O1	0.1670 (3)	−0.0064 (4)	0.5583 (3)	0.0388 (10)
N1	0.0665 (4)	−0.1720 (5)	0.5213 (4)	0.0413 (13)
C1	0.1230 (5)	−0.0969 (6)	0.4992 (5)	0.0361 (14)
C2	0.0194 (6)	−0.2655 (7)	0.4551 (6)	0.0488 (18)
H2A	0.0678	−0.3301	0.4584	0.059*
H2B	0.0002	−0.2325	0.3920	0.059*
C3	−0.0724 (6)	−0.3162 (7)	0.4743 (6)	0.0512 (19)
H3A	−0.1191	−0.2508	0.4744	0.061*
H3B	−0.0526	−0.3530	0.5361	0.061*
C4	−0.1253 (7)	−0.4091 (8)	0.4026 (7)	0.065 (2)
H4A	−0.1845	−0.4379	0.4167	0.097*
H4B	−0.0803	−0.4756	0.4040	0.097*
H4C	−0.1449	−0.3730	0.3412	0.097*
C5	0.1410 (6)	−0.0002 (8)	0.6435 (5)	0.0499 (19)
H5A	0.0687	−0.0055	0.6297	0.075*
H5B	0.1644	0.0752	0.6745	0.075*
H5C	0.1724	−0.0661	0.6837	0.075*
C6	0.4147 (4)	0.2585 (5)	0.5707 (4)	0.0285 (12)
C7	0.5023 (5)	0.3241 (6)	0.6067 (4)	0.0360 (14)
H7	0.5353	0.3561	0.5662	0.043*
C8	0.5413 (5)	0.3427 (6)	0.7009 (5)	0.0427 (16)
H8	0.6009	0.3867	0.7246	0.051*
C9	0.4926 (6)	0.2962 (7)	0.7608 (5)	0.0470 (17)
H9	0.5187	0.3096	0.8251	0.056*
C10	0.4067 (6)	0.2309 (7)	0.7263 (5)	0.0507 (19)
H10	0.3744	0.1991	0.7674	0.061*
C11	0.3664 (5)	0.2108 (7)	0.6318 (4)	0.0412 (15)
H11	0.3073	0.1657	0.6088	0.049*
C12	0.4645 (4)	0.2387 (5)	0.4006 (4)	0.0284 (12)
C13	0.5248 (5)	0.1371 (7)	0.4103 (5)	0.0429 (16)
H13	0.5071	0.0665	0.4355	0.052*
C14	0.6109 (6)	0.1398 (8)	0.3828 (6)	0.053 (2)
H14	0.6528	0.0722	0.3914	0.064*
C15	0.6347 (6)	0.2424 (8)	0.3428 (5)	0.0516 (19)
H15	0.6925	0.2442	0.3234	0.062*
C16	0.5748 (6)	0.3410 (8)	0.3311 (5)	0.053 (2)
H16	0.5918	0.4102	0.3038	0.064*
C17	0.4894 (5)	0.3408 (6)	0.3590 (4)	0.0371 (14)
H17	0.4483	0.4091	0.3500	0.045*
C18	0.2886 (5)	0.3729 (6)	0.4041 (4)	0.0331 (13)
C19	0.3025 (5)	0.4783 (7)	0.4533 (4)	0.0372 (15)
H19	0.3493	0.4819	0.5129	0.045*
C20	0.2475 (6)	0.5802 (7)	0.4153 (5)	0.050 (2)
H20	0.2549	0.6512	0.4503	0.060*
C21	0.1823 (6)	0.5762 (7)	0.3265 (5)	0.0487 (19)
H21	0.1466	0.6453	0.3001	0.058*
C22	0.1691 (6)	0.4714 (7)	0.2761 (5)	0.0472 (18)
H22	0.1235	0.4688	0.2159	0.057*
C23	0.2227 (5)	0.3702 (7)	0.3139 (5)	0.0432 (16)
H23	0.2148	0.2993	0.2789	0.052*

	U11	U22	U33	U12	U13	U23
Au	0.03095 (14)	0.02962 (14)	0.02940 (14)	−0.00472 (10)	0.00897 (9)	0.00101 (9)
S1	0.0416 (9)	0.0345 (8)	0.0341 (8)	−0.0110 (7)	0.0155 (7)	−0.0047 (7)
P1	0.0293 (8)	0.0287 (8)	0.0274 (7)	−0.0022 (6)	0.0067 (6)	0.0020 (6)
O1	0.039 (3)	0.046 (3)	0.036 (2)	−0.004 (2)	0.019 (2)	−0.003 (2)
N1	0.041 (3)	0.044 (3)	0.043 (3)	−0.010 (3)	0.018 (3)	0.000 (3)
C1	0.036 (3)	0.036 (3)	0.036 (3)	−0.001 (3)	0.011 (3)	0.002 (3)
C2	0.052 (5)	0.043 (4)	0.060 (5)	−0.017 (3)	0.030 (4)	−0.005 (4)
C3	0.040 (4)	0.052 (5)	0.066 (5)	−0.009 (3)	0.022 (4)	0.003 (4)
C4	0.062 (6)	0.065 (6)	0.068 (6)	−0.022 (5)	0.021 (4)	−0.002 (5)
C5	0.054 (5)	0.061 (5)	0.042 (4)	−0.011 (4)	0.027 (3)	−0.013 (4)
C6	0.029 (3)	0.031 (3)	0.025 (3)	0.002 (2)	0.007 (2)	0.002 (2)
C7	0.036 (3)	0.035 (3)	0.037 (3)	−0.006 (3)	0.012 (3)	0.006 (3)
C8	0.044 (4)	0.040 (4)	0.035 (3)	−0.001 (3)	−0.001 (3)	−0.002 (3)
C9	0.050 (4)	0.054 (5)	0.034 (3)	0.009 (4)	0.008 (3)	−0.006 (3)
C10	0.055 (5)	0.059 (5)	0.042 (4)	0.005 (4)	0.021 (3)	0.004 (4)
C11	0.039 (4)	0.051 (4)	0.036 (3)	0.002 (3)	0.015 (3)	0.002 (3)
C12	0.026 (3)	0.035 (3)	0.025 (3)	−0.005 (2)	0.008 (2)	−0.001 (2)
C13	0.044 (4)	0.038 (4)	0.050 (4)	0.007 (3)	0.019 (3)	0.014 (3)
C14	0.043 (4)	0.058 (5)	0.060 (5)	0.017 (4)	0.017 (4)	0.011 (4)
C15	0.049 (4)	0.071 (6)	0.041 (4)	0.001 (4)	0.023 (3)	−0.003 (4)
C16	0.064 (5)	0.051 (5)	0.058 (5)	−0.004 (4)	0.038 (4)	0.008 (4)
C17	0.047 (4)	0.031 (3)	0.039 (3)	0.002 (3)	0.021 (3)	0.005 (3)
C18	0.037 (3)	0.026 (3)	0.033 (3)	0.004 (3)	0.005 (3)	−0.001 (3)
C19	0.025 (3)	0.050 (4)	0.034 (3)	0.000 (3)	0.004 (2)	0.002 (3)
C20	0.065 (5)	0.036 (4)	0.049 (4)	0.007 (3)	0.016 (4)	−0.002 (3)
C21	0.050 (4)	0.053 (5)	0.046 (4)	0.013 (4)	0.019 (3)	0.018 (4)
C22	0.042 (4)	0.057 (5)	0.039 (4)	0.008 (4)	0.007 (3)	0.012 (3)
C23	0.044 (4)	0.043 (4)	0.039 (4)	−0.007 (3)	0.007 (3)	0.000 (3)

Au—S1	2.3089 (16)	C9—C10	1.367 (11)
Au—P1	2.2557 (16)	C9—H9	0.9400
S1—C1	1.775 (7)	C10—C11	1.385 (10)
P1—C12	1.813 (6)	C10—H10	0.9400
P1—C6	1.816 (6)	C11—H11	0.9400
P1—C18	1.821 (6)	C12—C13	1.394 (9)
O1—C1	1.364 (8)	C12—C17	1.396 (8)
O1—C5	1.440 (7)	C13—C14	1.387 (10)
N1—C1	1.265 (8)	C13—H13	0.9400
N1—C2	1.457 (9)	C14—C15	1.382 (11)
C2—C3	1.508 (9)	C14—H14	0.9400
C2—H2A	0.9800	C15—C16	1.361 (11)
C2—H2B	0.9800	C15—H15	0.9400
C3—C4	1.520 (11)	C16—C17	1.380 (10)
C3—H3A	0.9800	C16—H16	0.9400
C3—H3B	0.9800	C17—H17	0.9400
C4—H4A	0.9700	C18—C19	1.373 (9)
C4—H4B	0.9700	C18—C23	1.395 (9)
C4—H4C	0.9700	C19—C20	1.395 (10)
C5—H5A	0.9700	C19—H19	0.9400
C5—H5B	0.9700	C20—C21	1.375 (10)
C5—H5C	0.9700	C20—H20	0.9400
C6—C7	1.389 (8)	C21—C22	1.377 (11)
C6—C11	1.402 (9)	C21—H21	0.9400
C7—C8	1.377 (9)	C22—C23	1.380 (10)
C7—H7	0.9400	C22—H22	0.9400
C8—C9	1.388 (10)	C23—H23	0.9400
C8—H8	0.9400
P1—Au—S1	176.71 (6)	C10—C9—C8	120.0 (6)
C1—S1—Au	102.0 (2)	C10—C9—H9	120.0
C12—P1—C6	104.3 (3)	C8—C9—H9	120.0
C12—P1—C18	105.6 (3)	C9—C10—C11	121.1 (7)
C6—P1—C18	105.5 (3)	C9—C10—H10	119.5
C12—P1—Au	117.2 (2)	C11—C10—H10	119.5
C6—P1—Au	110.9 (2)	C10—C11—C6	119.3 (7)
C18—P1—Au	112.3 (2)	C10—C11—H11	120.4
C1—O1—C5	115.8 (5)	C6—C11—H11	120.4
C1—N1—C2	118.9 (6)	C13—C12—C17	119.1 (6)
N1—C1—O1	120.8 (6)	C13—C12—P1	119.1 (5)
N1—C1—S1	127.1 (5)	C17—C12—P1	121.8 (5)
O1—C1—S1	112.1 (5)	C14—C13—C12	120.2 (7)
N1—C2—C3	111.8 (6)	C14—C13—H13	119.9
N1—C2—H2A	109.3	C12—C13—H13	119.9
C3—C2—H2A	109.3	C15—C14—C13	119.6 (7)
N1—C2—H2B	109.3	C15—C14—H14	120.2
C3—C2—H2B	109.3	C13—C14—H14	120.2
H2A—C2—H2B	107.9	C16—C15—C14	120.4 (7)
C2—C3—C4	112.2 (7)	C16—C15—H15	119.8
C2—C3—H3A	109.2	C14—C15—H15	119.8
C4—C3—H3A	109.2	C15—C16—C17	121.0 (7)
C2—C3—H3B	109.2	C15—C16—H16	119.5
C4—C3—H3B	109.2	C17—C16—H16	119.5
H3A—C3—H3B	107.9	C16—C17—C12	119.6 (7)
C3—C4—H4A	109.5	C16—C17—H17	120.2
C3—C4—H4B	109.5	C12—C17—H17	120.2
H4A—C4—H4B	109.5	C19—C18—C23	119.4 (6)
C3—C4—H4C	109.5	C19—C18—P1	123.6 (5)
H4A—C4—H4C	109.5	C23—C18—P1	116.9 (5)
H4B—C4—H4C	109.5	C18—C19—C20	120.4 (6)
O1—C5—H5A	109.5	C18—C19—H19	119.8
O1—C5—H5B	109.5	C20—C19—H19	119.8
H5A—C5—H5B	109.5	C21—C20—C19	119.7 (7)
O1—C5—H5C	109.5	C21—C20—H20	120.2
H5A—C5—H5C	109.5	C19—C20—H20	120.2
H5B—C5—H5C	109.5	C20—C21—C22	120.3 (7)
C7—C6—C11	119.1 (6)	C20—C21—H21	119.8
C7—C6—P1	121.8 (5)	C22—C21—H21	119.8
C11—C6—P1	119.0 (5)	C23—C22—C21	120.0 (7)
C8—C7—C6	120.6 (6)	C23—C22—H22	120.0
C8—C7—H7	119.7	C21—C22—H22	120.0
C6—C7—H7	119.7	C22—C23—C18	120.1 (7)
C7—C8—C9	119.9 (7)	C22—C23—H23	119.9
C7—C8—H8	120.0	C18—C23—H23	119.9
C9—C8—H8	120.0
C2—N1—C1—O1	178.7 (6)	C6—P1—C12—C17	−99.5 (5)
C2—N1—C1—S1	−1.6 (10)	C18—P1—C12—C17	11.5 (6)
C5—O1—C1—N1	−2.7 (9)	Au—P1—C12—C17	137.5 (5)
C5—O1—C1—S1	177.6 (5)	C17—C12—C13—C14	3.0 (10)
Au—S1—C1—N1	−179.7 (6)	P1—C12—C13—C14	−174.6 (6)
Au—S1—C1—O1	0.1 (5)	C12—C13—C14—C15	−2.3 (12)
C1—N1—C2—C3	−158.4 (7)	C13—C14—C15—C16	0.7 (13)
N1—C2—C3—C4	176.9 (7)	C14—C15—C16—C17	0.1 (13)
C12—P1—C6—C7	29.9 (6)	C15—C16—C17—C12	0.7 (12)
C18—P1—C6—C7	−81.2 (6)	C13—C12—C17—C16	−2.2 (10)
Au—P1—C6—C7	156.9 (5)	P1—C12—C17—C16	175.3 (6)
C12—P1—C6—C11	−151.9 (5)	C12—P1—C18—C19	−93.4 (6)
C18—P1—C6—C11	97.1 (6)	C6—P1—C18—C19	16.7 (7)
Au—P1—C6—C11	−24.8 (6)	Au—P1—C18—C19	137.7 (5)
C11—C6—C7—C8	−0.3 (10)	C12—P1—C18—C23	81.9 (6)
P1—C6—C7—C8	177.9 (5)	C6—P1—C18—C23	−167.9 (5)
C6—C7—C8—C9	−0.4 (11)	Au—P1—C18—C23	−46.9 (6)
C7—C8—C9—C10	0.8 (11)	C23—C18—C19—C20	3.2 (10)
C8—C9—C10—C11	−0.5 (12)	P1—C18—C19—C20	178.5 (6)
C9—C10—C11—C6	−0.1 (12)	C18—C19—C20—C21	−2.9 (11)
C7—C6—C11—C10	0.5 (10)	C19—C20—C21—C22	1.9 (12)
P1—C6—C11—C10	−177.8 (6)	C20—C21—C22—C23	−1.2 (12)
C6—P1—C12—C13	78.1 (6)	C21—C22—C23—C18	1.5 (11)
C18—P1—C12—C13	−170.9 (5)	C19—C18—C23—C22	−2.6 (11)
Au—P1—C12—C13	−45.0 (6)	P1—C18—C23—C22	−178.1 (6)

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14···O1i	0.94	2.51	3.314 (10)	143

Table 1

Selected bond lengths (Å)

Au—S1	2.3089 (16)
Au—P1	2.2557 (16)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C14—H14⋯O1i	0.94	2.51	3.314 (10)	143

Symmetry code: (i) .