{O-Ethyl (Z)-[4-(methoxy­carbon­yl)phen­yl]thio­carbamato-κS}(triethyl­phosphine-κP)gold(I)–{O-ethyl (Z)-[4-(ethoxy­carbon­yl)phen­yl]thio­carbamato-κS}(triethyl­phosphine-κP)gold(I) (1/1)

A linear coordination geometry defined by S and P atoms is found for Au in both components of the title 1:1 cocrystal, [Au(C₆H₁₅P)(C₁₁H₁₂NO₃S)]·[Au(C₆H₁₅P)(C₁₂H₁₄NO₃S)]. Pairs of molecules disordered over an inversion centre associate via Au...·S inter­actions and these dimeric units are connected into chains via C—H...O inter­actions.

Key indicators

• Single-crystal X-ray study
• T = 223 K
• Mean [sigma](C-C) = 0.008 Å
• Disorder in main residue
• R factor = 0.031
• wR factor = 0.078
• Data-to-parameter ratio = 18.6

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT220_ALERT_2_B Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.57 Ratio
PLAT241_ALERT_2_B Check High      Ueq as Compared to Neighbors for         C9

Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       0.81
PLAT301_ALERT_3_C Main Residue  Disorder .........................      12.00 Perc.
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          3

Alert level G
ABSTM02_ALERT_3_G  When printed, the submitted absorption T values will be
            replaced by the scaled T values. Since the ratio of scaled T's
            is identical to the ratio of reported T values, the scaling
            does not imply a change to the absorption corrections used in
            the study.
            Ratio of Tmax expected/reported      0.806
            Tmax scaled      0.806 Tmin scaled      0.256

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

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 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
   2 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

---

Computing details

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: PATTY in DIRDIF92 (Beurskens et al., 1992); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: SHELXL97.

{O-Ethyl (Z)-[4-(methoxycarbonyl)phenyl]thiocarbamato- κS}(triethylphosphine-κP)gold(I)– {O-ethyl (Z)-[4-(ethoxycarbonyl)phenyl]thiocarbamato- κS}(triethylphosphine-κP)gold(I) (1/1)

Crystal data

[Au(C6H15P)(C11H12NO3S)]·[Au(C6H15P)(C12H14NO3S)]	Z = 1
Mr = 1120.81	F(000) = 548
Triclinic, P1	Dx = 1.772 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71069 Å
a = 7.6246 (3) Å	Cell parameters from 3917 reflections
b = 10.3422 (4) Å	θ = 2.7–29.9°
c = 14.5155 (5) Å	µ = 7.20 mm^−1
α = 79.678 (2)°	T = 223 K
β = 79.451 (1)°	Plate, colourless
γ = 70.188 (2)°	0.34 × 0.10 × 0.03 mm
V = 1050.15 (7) Å^3

Data collection

Bruker SMART CCD diffractometer	4806 independent reflections
Radiation source: fine-focus sealed tube	4294 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.028
ω scans	θmax = 27.5°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −9→9
Tmin = 0.318, Tmax = 1	k = −10→13
7470 measured reflections	l = −18→18

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.031	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.078	H-atom parameters constrained
S = 1.00	w = 1/[σ^2(Fo^2) + (0.0402P)^2] where P = (Fo^2 + 2Fc^2)/3
4806 reflections	(Δ/σ)max < 0.001
259 parameters	Δρmax = 1.48 e Å^−3
53 restraints	Δρmin = −1.52 e Å^−3

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'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 > σ(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 (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
Au	0.72752 (2)	0.371568 (16)	0.534748 (12)	0.02664 (7)
S1	0.65345 (16)	0.33583 (12)	0.39585 (9)	0.0313 (3)
P1	0.81159 (17)	0.39341 (12)	0.67109 (9)	0.0257 (2)
O1	0.2822 (17)	0.1792 (12)	0.0204 (11)	0.058 (4)	0.50
O2	0.290 (3)	0.3987 (13)	−0.0165 (11)	0.057 (4)	0.50
O1'	0.2306 (15)	0.2067 (12)	0.0358 (10)	0.051 (3)	0.50
O2'	0.328 (3)	0.3813 (12)	−0.0329 (10)	0.051 (4)	0.50
O3	0.9864 (4)	0.1589 (3)	0.4144 (2)	0.0296 (7)
N1	0.8617 (6)	0.1273 (4)	0.2930 (3)	0.0312 (9)
C1	0.8473 (6)	0.1947 (4)	0.3597 (3)	0.0250 (9)
C2	0.7267 (7)	0.1692 (5)	0.2307 (3)	0.0296 (10)
C3	0.7032 (8)	0.2894 (5)	0.1677 (4)	0.0380 (12)
H3	0.7727	0.3482	0.1700	0.046*
C4	0.5809 (8)	0.3251 (6)	0.1018 (4)	0.0399 (12)
H4	0.5668	0.4075	0.0600	0.048*
C5	0.4769 (7)	0.2379 (5)	0.0972 (3)	0.0348 (11)
C6	0.4990 (7)	0.1185 (5)	0.1604 (4)	0.0383 (12)
H6	0.4289	0.0600	0.1586	0.046*
C7	0.6225 (7)	0.0839 (5)	0.2261 (4)	0.0369 (11)
H7	0.6363	0.0018	0.2682	0.044*
C8	0.3389 (6)	0.2830 (5)	0.0268 (3)	0.0465 (14)
C9	0.146 (2)	0.2083 (19)	−0.0458 (12)	0.090 (7)	0.50
H9A	0.2131	0.2029	−0.1102	0.108*	0.50
H9B	0.0593	0.3026	−0.0429	0.108*	0.50
C10	0.038 (2)	0.1079 (16)	−0.0236 (11)	0.068 (4)	0.50
H10A	−0.0680	0.1408	−0.0593	0.102*	0.50
H10B	−0.0077	0.0996	0.0434	0.102*	0.50
H10C	0.1188	0.0181	−0.0404	0.102*	0.50
C9'	0.0904 (19)	0.2423 (17)	−0.0291 (10)	0.060 (4)	0.50
H9'A	0.0419	0.1657	−0.0247	0.090*	0.50
H9'B	0.1484	0.2606	−0.0932	0.090*	0.50
H9'C	−0.0119	0.3242	−0.0124	0.090*	0.50
C11	1.1513 (6)	0.0435 (5)	0.3880 (4)	0.0318 (10)
H11A	1.1989	0.0599	0.3210	0.038*
H11B	1.1198	−0.0429	0.3992	0.038*
C12	1.2959 (7)	0.0345 (6)	0.4488 (4)	0.0405 (12)
H12A	1.4030	−0.0479	0.4393	0.061*
H12B	1.2413	0.0298	0.5146	0.061*
H12C	1.3366	0.1159	0.4315	0.061*
C13	0.8288 (7)	0.5616 (5)	0.6800 (4)	0.0310 (10)
H13A	0.9014	0.5907	0.6219	0.037*
H13B	0.7020	0.6289	0.6839	0.037*
C14	0.9197 (8)	0.5667 (5)	0.7640 (4)	0.0403 (12)
H14A	0.9081	0.6620	0.7679	0.060*
H14B	1.0516	0.5121	0.7559	0.060*
H14C	0.8570	0.5294	0.8217	0.060*
C15	1.0416 (7)	0.2701 (5)	0.6884 (4)	0.0328 (11)
H15A	1.0700	0.2736	0.7509	0.039*
H15B	1.0395	0.1764	0.6866	0.039*
C16	1.1957 (7)	0.3000 (6)	0.6133 (5)	0.0461 (14)
H16A	1.3132	0.2258	0.6202	0.069*
H16B	1.2104	0.3869	0.6207	0.069*
H16C	1.1616	0.3061	0.5511	0.069*
C17	0.6556 (8)	0.3566 (5)	0.7750 (4)	0.0374 (12)
H17A	0.7035	0.3648	0.8312	0.045*
H17B	0.5313	0.4264	0.7725	0.045*
C18	0.6345 (10)	0.2131 (6)	0.7851 (5)	0.0572 (17)
H18A	0.5465	0.2012	0.8408	0.086*
H18B	0.7558	0.1430	0.7913	0.086*
H18C	0.5877	0.2038	0.7296	0.086*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Au	0.02665 (10)	0.02687 (11)	0.02695 (11)	−0.00364 (7)	−0.00873 (7)	−0.00907 (7)
S1	0.0253 (6)	0.0338 (6)	0.0321 (7)	0.0045 (5)	−0.0147 (5)	−0.0137 (5)
P1	0.0287 (6)	0.0254 (6)	0.0245 (6)	−0.0063 (5)	−0.0084 (5)	−0.0066 (5)
O1	0.065 (7)	0.065 (6)	0.056 (7)	−0.019 (5)	−0.035 (6)	−0.016 (5)
O2	0.058 (8)	0.070 (7)	0.036 (6)	−0.012 (5)	−0.020 (5)	0.013 (5)
O1'	0.036 (5)	0.072 (7)	0.046 (6)	−0.015 (5)	−0.016 (4)	−0.006 (5)
O2'	0.051 (7)	0.066 (7)	0.033 (6)	−0.015 (5)	−0.013 (5)	0.003 (5)
O3	0.0223 (15)	0.0296 (16)	0.0338 (19)	0.0025 (13)	−0.0111 (13)	−0.0097 (14)
N1	0.036 (2)	0.027 (2)	0.031 (2)	−0.0034 (16)	−0.0128 (18)	−0.0108 (17)
C1	0.026 (2)	0.023 (2)	0.025 (2)	−0.0025 (17)	−0.0080 (18)	−0.0048 (17)
C2	0.031 (2)	0.029 (2)	0.028 (3)	−0.0034 (19)	−0.0057 (19)	−0.0105 (19)
C3	0.051 (3)	0.032 (3)	0.037 (3)	−0.016 (2)	−0.020 (2)	−0.002 (2)
C4	0.056 (3)	0.038 (3)	0.030 (3)	−0.017 (2)	−0.019 (2)	0.003 (2)
C5	0.040 (3)	0.041 (3)	0.025 (3)	−0.010 (2)	−0.011 (2)	−0.007 (2)
C6	0.041 (3)	0.037 (3)	0.041 (3)	−0.012 (2)	−0.014 (2)	−0.005 (2)
C7	0.046 (3)	0.029 (2)	0.036 (3)	−0.010 (2)	−0.014 (2)	0.001 (2)
C8	0.049 (3)	0.065 (4)	0.027 (3)	−0.017 (3)	−0.009 (2)	−0.007 (3)
C9	0.099 (11)	0.101 (11)	0.089 (11)	−0.035 (8)	−0.047 (8)	−0.016 (8)
C10	0.053 (6)	0.102 (8)	0.064 (7)	−0.027 (6)	−0.020 (6)	−0.029 (6)
C9'	0.058 (7)	0.084 (8)	0.042 (7)	−0.019 (6)	−0.030 (6)	−0.002 (6)
C11	0.028 (2)	0.027 (2)	0.035 (3)	0.0025 (18)	−0.006 (2)	−0.010 (2)
C12	0.029 (3)	0.038 (3)	0.051 (4)	−0.001 (2)	−0.013 (2)	−0.008 (2)
C13	0.034 (2)	0.028 (2)	0.034 (3)	−0.0095 (19)	−0.009 (2)	−0.0069 (19)
C14	0.043 (3)	0.040 (3)	0.046 (3)	−0.014 (2)	−0.010 (2)	−0.020 (2)
C15	0.038 (3)	0.027 (2)	0.034 (3)	−0.0040 (19)	−0.015 (2)	−0.006 (2)
C16	0.032 (3)	0.043 (3)	0.058 (4)	0.000 (2)	−0.006 (3)	−0.015 (3)
C17	0.047 (3)	0.037 (3)	0.031 (3)	−0.019 (2)	0.004 (2)	−0.012 (2)
C18	0.082 (5)	0.054 (4)	0.050 (4)	−0.044 (3)	0.011 (3)	−0.017 (3)

Geometric parameters (Å, º)

Au—S1	2.3122 (12)	C10—H10A	0.9700
Au—P1	2.2587 (12)	C10—H10B	0.9700
S1—C1	1.766 (4)	C10—H10C	0.9700
P1—C17	1.811 (5)	C9'—H9'A	0.9700
P1—C15	1.815 (5)	C9'—H9'B	0.9700
P1—C13	1.817 (5)	C9'—H9'C	0.9700
O1—C8	1.308 (9)	C11—C12	1.503 (7)
O1—C9	1.461 (9)	C11—H11A	0.9800
O2—C8	1.216 (9)	C11—H11B	0.9800
O1'—C8	1.299 (8)	C12—H12A	0.9700
O1'—C9'	1.463 (9)	C12—H12B	0.9700
O2'—C8	1.201 (9)	C12—H12C	0.9700
O3—C1	1.352 (5)	C13—C14	1.526 (7)
O3—C11	1.457 (5)	C13—H13A	0.9800
N1—C1	1.261 (6)	C13—H13B	0.9800
N1—C2	1.401 (6)	C14—H14A	0.9700
C2—C3	1.384 (7)	C14—H14B	0.9700
C2—C7	1.389 (7)	C14—H14C	0.9700
C3—C4	1.373 (7)	C15—C16	1.524 (8)
C3—H3	0.9400	C15—H15A	0.9800
C4—C5	1.404 (7)	C15—H15B	0.9800
C4—H4	0.9400	C16—H16A	0.9700
C5—C6	1.379 (7)	C16—H16B	0.9700
C5—C8	1.503 (7)	C16—H16C	0.9700
C6—C7	1.380 (7)	C17—C18	1.525 (7)
C6—H6	0.9400	C17—H17A	0.9800
C7—H7	0.9400	C17—H17B	0.9800
C9—C10	1.494 (10)	C18—H18A	0.9700
C9—H9A	0.9800	C18—H18B	0.9700
C9—H9B	0.9800	C18—H18C	0.9700
S1—Au—P1	176.60 (4)	H9'A—C9'—H9'C	109.5
Au—S1—C1	103.11 (16)	H9'B—C9'—H9'C	109.5
C17—P1—C15	105.3 (2)	O3—C11—C12	106.3 (4)
C17—P1—C13	105.4 (2)	O3—C11—H11A	110.5
C15—P1—C13	105.5 (2)	C12—C11—H11A	110.5
C17—P1—Au	113.57 (18)	O3—C11—H11B	110.5
C15—P1—Au	110.17 (17)	C12—C11—H11B	110.5
C13—P1—Au	116.10 (17)	H11A—C11—H11B	108.7
C8—O1—C9	115.4 (12)	C11—C12—H12A	109.5
C8—O1'—C9'	118.6 (13)	C11—C12—H12B	109.5
C1—O3—C11	115.5 (4)	H12A—C12—H12B	109.5
C1—N1—C2	121.5 (4)	C11—C12—H12C	109.5
N1—C1—O3	120.5 (4)	H12A—C12—H12C	109.5
N1—C1—S1	126.7 (4)	H12B—C12—H12C	109.5
O3—C1—S1	112.7 (3)	C14—C13—P1	115.2 (3)
C3—C2—C7	118.2 (5)	C14—C13—H13A	108.5
C3—C2—N1	121.8 (4)	P1—C13—H13A	108.5
C7—C2—N1	119.8 (4)	C14—C13—H13B	108.5
C4—C3—C2	121.7 (5)	P1—C13—H13B	108.5
C4—C3—H3	119.1	H13A—C13—H13B	107.5
C2—C3—H3	119.1	C13—C14—H14A	109.5
C3—C4—C5	119.8 (5)	C13—C14—H14B	109.5
C3—C4—H4	120.1	H14A—C14—H14B	109.5
C5—C4—H4	120.1	C13—C14—H14C	109.5
C6—C5—C4	118.7 (5)	H14A—C14—H14C	109.5
C6—C5—C8	123.0 (4)	H14B—C14—H14C	109.5
C4—C5—C8	118.3 (4)	C16—C15—P1	112.0 (4)
C5—C6—C7	120.9 (5)	C16—C15—H15A	109.2
C5—C6—H6	119.5	P1—C15—H15A	109.2
C7—C6—H6	119.5	C16—C15—H15B	109.2
C6—C7—C2	120.7 (5)	P1—C15—H15B	109.2
C6—C7—H7	119.6	H15A—C15—H15B	107.9
C2—C7—H7	119.6	C15—C16—H16A	109.5
O2'—C8—O1'	122.5 (16)	C15—C16—H16B	109.5
O2—C8—O1'	118.3 (15)	H16A—C16—H16B	109.5
O2'—C8—O1	123.9 (15)	C15—C16—H16C	109.5
O2—C8—O1	126.5 (16)	H16A—C16—H16C	109.5
O2'—C8—C5	123.3 (14)	H16B—C16—H16C	109.5
O2—C8—C5	124.2 (15)	C18—C17—P1	113.7 (4)
O1'—C8—C5	114.3 (8)	C18—C17—H17A	108.8
O1—C8—C5	109.3 (8)	P1—C17—H17A	108.8
O1—C9—C10	111.4 (11)	C18—C17—H17B	108.8
O1—C9—H9A	109.4	P1—C17—H17B	108.8
C10—C9—H9A	109.4	H17A—C17—H17B	107.7
O1—C9—H9B	109.4	C17—C18—H18A	109.5
C10—C9—H9B	109.4	C17—C18—H18B	109.5
H9A—C9—H9B	108.0	H18A—C18—H18B	109.5
O1'—C9'—H9'A	109.5	C17—C18—H18C	109.5
O1'—C9'—H9'B	109.5	H18A—C18—H18C	109.5
H9'A—C9'—H9'B	109.5	H18B—C18—H18C	109.5
O1'—C9'—H9'C	109.5
C2—N1—C1—O3	−174.7 (4)	C9—O1—C8—O2	0.1 (4)
C2—N1—C1—S1	7.5 (7)	C9—O1—C8—O1'	72 (4)
C11—O3—C1—N1	2.3 (6)	C9—O1—C8—C5	179.9 (2)
C11—O3—C1—S1	−179.6 (3)	C6—C5—C8—O2'	−174.4 (8)
Au—S1—C1—N1	171.4 (4)	C4—C5—C8—O2'	8.9 (7)
Au—S1—C1—O3	−6.5 (3)	C6—C5—C8—O2	164.9 (8)
C1—N1—C2—C3	67.7 (7)	C4—C5—C8—O2	−11.7 (8)
C1—N1—C2—C7	−117.3 (5)	C6—C5—C8—O1'	5.7 (8)
C7—C2—C3—C4	−0.1 (8)	C4—C5—C8—O1'	−171.0 (7)
N1—C2—C3—C4	175.0 (5)	C6—C5—C8—O1	−14.9 (7)
C2—C3—C4—C5	−0.3 (9)	C4—C5—C8—O1	168.4 (7)
C3—C4—C5—C6	0.8 (8)	C8—O1—C9—C10	−158.9 (15)
C3—C4—C5—C8	177.6 (5)	C1—O3—C11—C12	172.5 (4)
C4—C5—C6—C7	−0.9 (8)	C17—P1—C13—C14	64.1 (4)
C8—C5—C6—C7	−177.6 (5)	C15—P1—C13—C14	−47.0 (4)
C5—C6—C7—C2	0.5 (9)	Au—P1—C13—C14	−169.3 (3)
C3—C2—C7—C6	0.0 (8)	C17—P1—C15—C16	−172.0 (4)
N1—C2—C7—C6	−175.2 (5)	C13—P1—C15—C16	−60.9 (4)
C9'—O1'—C8—O2'	−0.2 (4)	Au—P1—C15—C16	65.1 (4)
C9'—O1'—C8—O2	19.1 (12)	C15—P1—C17—C18	−64.1 (5)
C9'—O1'—C8—O1	−101 (4)	C13—P1—C17—C18	−175.4 (5)
C9'—O1'—C8—C5	179.7 (3)	Au—P1—C17—C18	56.4 (5)
C9—O1—C8—O2'	−20.7 (12)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···O2^i	0.94	2.53	3.295 (18)	139
C4—H4···O2′^i	0.94	2.52	3.285 (17)	139

Symmetry code: (i) −x+1, −y+1, −z.