1,2-Di­cyano-1,2-bis­(imidazolidine-2-thione)­digold(I) and 2,2-di­cyano-1,1-bis­(di­methyl­thio­urea)­digold(I)

Gold(I) cyanide forms complexes with imidazolidine-2-thione (etu) and di­methyl­thio­urea (dmtu) with the formula [Au₂(CN)₂L₂], i.e. the title complexes di­cyano-1κC,2κC-bis(imidazolidine-2-thione)-1κS,2κS-digold(I)(Au—Au), [Au₂(CN)₂(C₃H₆N₂S)₂], and di­cyano-1κ²C-bis(N,N′-di­methyl­thio­urea)-2κ²S-digold(I)(Au—Au), [Au₂(CN)₂(C₃H₈N₂S)₂]. In the etu complex, two approximately linear (etu)AuCN groups are held together by a weak homopolar Au—Au bond [3.117 (1) Å], with a torsion angle of 61 (3)° between the two groups. In the dmtu complex, an approximately linear Au(dmtu)₂ group is bound to an approximately linear Au(CN)₂ group by a weak heteropolar Au—Au bond [3.091 (1) Å], with a torsion angle of 83 (5)° between the two groups.

S1. Comment

We have reported previously the preparation and structures of complexes of thioureas with copper(I) cyanide (Stocker et al., 1996) and with silver(I) cyanide (Stocker et al., 1999). We report here an extension of this work to gold(I) cyanide. The sulfur ligands used previously included thiourea (tu), 1-methyl-2-thiourea (mtu), 1,3-dimethyl-2-thiourea, 1,3-diethyl-2-thiourea (detu), 1,1,3,3-tetramethylthiourea (tmtu) and 2-imidalozidinethione (N,N-ethylenethiourea, etu). For the purposes of comparison, syntheses were attempted of the gold cyanide complexes of all of these ligands. Crystalline products could only be obtained with dmtu and etu, and the structures of 1,2-dicyano-1,2-bis(imidazolidine-2-thione)digold(I), (I), and 2,2-dicyano-1,1-bis(dimethylthiourea)digold(I), (II), are reported here.

Ellipsoid plots showing the atom labelling are shown in Figs. 1 and 2 for (I) and (II), respectively. In each case, there is a molecule containing two Au atoms, two CN groups and two thioureas, and the molecule is shaped like a twisted letter H with two approximately linear AuX₂ or AuXY groups held together by a weak Au—Au bond. Because the end groups are not exactly linear, the torsion angles around the Au—Au bond are not well defined. An average torsion angle can be obtained from the four individual torsion angles involving the Au—Au bond; these are 61 (3)° for the etu complex and 83 (5)° for the dmtu complex.

The two molecules differ, however, in that the etu complex contains two (etu)AuCN groups, while in the dmtu complex, there is one Au(dmtu)₂ group and one Au(CN)₂ group. It is somewhat surprising that such a minor chemical change in the ligand in going from etu to dmtu should lead to a change in the isomer of [Au₂(CN)₂L₂] that is formed. Although the two compounds appear to be quite different in that the Au—Au bond in the etu complex is non-polar, while that in the dmtu complex is polar, the occurrence of the two forms suggests that they differ very little in energy.

Every H atom attached to nitrogen in both structures is involved in hydrogen bonding (Tables 2 and 4).

Gold compounds of this sort are well known. Bis[iodo(trimethylphosphine)gold(I)] (Ahrland et al., 1987 is an example of a non-polar Au—Au complex (Au—Au 3.169 Å and torsion angle 70°). Bis(imidazolidene-2-thione)gold(I) diiodoaurate (Friedrichs & Jones, 1999) is an example of a polar isomer with etu as a ligand (3.270 Å and 74°). Dicyanobis[tris(2-cyanoethyl)phosphine]digold (Hussain et al., 1996) is an example containing the Au(CN)₂ group (3.270 Å and 80°).

It is worth noting that the etu complex could be planar and have a center of symmetry; the sizes of the C and S atoms do not preclude such an arrangement. While it is possible that packing forces account for the lack of a center, none of the 13 Au₂ complexes in the current version of the Cambridge Structural Database (Allen & Kennard, 1993) has a torsion angle around the Au—Au bond of less than 60°. This suggests that perhaps a torsion angle near 90° is favored energetically in the isolated molecule.

In both of the complexes reported here, there are Au—Au bonds, terminal CN groups and discrete molecules. This is different from the situation when the metal is Cu or Ag. In the seven complexes of CuCN with various thioureas (Stocker et al., 1996), there are 14 crystallographically different CN groups, 13 of which bridge between two Cu atoms. There are no Cu—Cu bonds. In the six complexes of AgCN with various thioureas (Stocker et al., 1999), there are nine crystallographically different CN groups, five of which bridge between two Ag atoms, and one of which is involved in what appears to be a three-center bond with two Ag atoms. The latter is the only example of a direct Ag—Ag interaction in any of the six complexes. About half of the time in both the Cu and Ag complexes, the S form bridges between the metal atoms. As a consequence of the CN and S bridges, all of the Cu and Ag complexes have polymeric solid-state structures. In the two examples presented here, the direct Au—Au bonds, which have no parallel in the Cu or Ag structures, lead to a completely different structural chemistry.

S2. Experimental

Commercial chemicals were used without further purification. For the preparation of AuCN(etu), (I), AuCN (56 mg, 0.25 mmol) was added to a solution of etu (177 mg, 1.67 mmol) in distilled water (10 ml). After heating to 363 K, a colorless solution was obtained which was filtered hot. Upon cooling, colorless crystals separated out (yield: 47 mg, 69%). IR (KBr): 3460 (m), 3220 (br s), 3070 (w), 2890 (m), 2155 (s), 1540 (s), 1482 (w), 1375 (m), 1320 (m), 1285 (s), 1212 (m), 1043 (w), 1015 (w), 997 (w), 917 (m), 750 (br m), 660 (w), 585 (br m), 495 (w), 445 (m) cm⁻¹. Analysis calculated for C₄H₆AuN₃S: C 14.78, H 1.86, N 12.92, S 9.86%; found: C 14.94, H 1.59, N 13.01, S, 9.73. For the preparation of AuCN(dmtu), (II), AuCN (56 mg, 0.25 mmol) was added to a solution of dmtu (661 mg, 5.0 mmol) dissolved in distilled water (10 ml). Mild heating (343 K) for about 30 min produced a clear colorless solution. Upon cooling, small block-like colorless crystals were deposited (yield: 60 mg, 73%). IR (KBr): 3385 (m), 3290 (s), 3235 (sh w), 3175 (w), 2960 (w), 2150 (s), 1617 (m), 1595 (s), 1530 (m), 1505 (s), 1455 (m), 1422 (m), 1375 (w), 1290 (s), 1190 (m), 1148 (w), 1042 (m), 1015 (w), 725 (m), 630 (w), 605 (w), 510 (m), 428 (w) cm⁻¹. Analysis calculated for C₄H₈AuN₃S: C 14.69, H 2.46, N 12.84, S 9.80%; found: C 14.72, H 2.57, N 12.86, S 9.76.

S3. Refinement

In the final difference map for the etu compound there are 21 peaks and valleys with magnitudes greater than 0.75 e Å⁻³; for the dtmu compound there are 15 suck peaks. In both cases, all of these are between 0.85 and 1.20 Å from one or the other of the Au atoms.

Computing details

For both compounds, data collection: ASTRO (Siemens, 1995); cell refinement: SAINT (Siemens, 1995); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 1994); program(s) used to refine structure: SHELXLTL; molecular graphics: SHELXLTL; software used to prepare material for publication: SHELXLTL.

Figures

	Fig. 1. Plot of the etu complex with displacement ellipsoids shown at the 50% probability level. H atoms are shown with arbitrary size.
	Fig. 2. Plot of the dtmu complex with displacement ellipsoids shown at the 50% probability level. H atoms are shown with arbitrary size.

(I) 1,2-bis(imidazolidine-2-thione)-1,2-dicyano-digold(I)

Crystal data

[Au2(CN)2(C3H6N2S)2]	Z = 2
Mr = 650.28	F(000) = 584
Triclinic, P1	Dx = 2.966 Mg m^−3
a = 7.4654 (15) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.233 (2) Å	Cell parameters from 1873 reflections
c = 11.895 (2) Å	θ = 1.8–25.0°
α = 103.73 (3)°	µ = 20.40 mm^−1
β = 90.73 (3)°	T = 174 K
γ = 112.98 (3)°	Flat needle, colorless
V = 728.1 (3) Å^3	0.30 × 0.10 × 0.06 mm

Data collection

Siemens SMART area-detector diffractometer	2545 independent reflections
Radiation source: fine-focus sealed tube	2124 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.045
ω scans	θmax = 25.0°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996; Blessing, 1995)	h = −8→8
Tmin = 0.10, Tmax = 0.29	k = −10→10
5410 measured reflections	l = −14→14

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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.093	H-atom parameters constrained
S = 0.94	Calculated w = 1/[σ^2(Fo^2) + (0.065P)^2] where P = (Fo^2 + 2Fc^2)/3
2545 reflections	(Δ/σ)max = −0.005
163 parameters	Δρmax = 1.91 e Å^−3
0 restraints	Δρmin = −1.52 e Å^−3

Special details

Experimental. IR spectra were recorded as KBr pellets with a Perkin-Elmer Model 1430 spectrophotometer. Elemental analyses were determined by Galbraith Laboratries, Knoxville, TN.

Refinement. There are 21 peaks and valleys in the final difference map with magnitudes greater tan 0.75 e/Å₃. All of these are between 0.85 and 1.10 Å from one or the other of the Au atoms.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Au1	0.67083 (5)	−0.04212 (4)	0.08277 (3)	0.04509 (15)
C1	0.4754 (14)	−0.2554 (12)	0.0901 (8)	0.046 (2)
N1	0.3700 (13)	−0.3747 (11)	0.1014 (8)	0.064 (2)
Au2	0.61049 (5)	0.13230 (4)	0.32865 (3)	0.04403 (15)
C2	0.6772 (16)	−0.0092 (13)	0.4061 (8)	0.056 (3)
N2	0.7093 (16)	−0.0937 (13)	0.4505 (9)	0.075 (3)
S1	0.9199 (4)	0.2049 (3)	0.0905 (2)	0.0599 (7)
C11	0.9555 (12)	0.2090 (10)	−0.0501 (7)	0.043 (2)
N11	0.8629 (11)	0.0908 (9)	−0.1444 (6)	0.051 (2)
H11	0.7729 (11)	−0.0015 (9)	−0.1428 (6)	0.061*
N12	1.0886 (11)	0.3334 (9)	−0.0788 (7)	0.055 (2)
H12	1.1635 (11)	0.4224 (9)	−0.0291 (7)	0.066*
C12	0.9290 (17)	0.1331 (15)	−0.2521 (10)	0.074 (3)
H12A	0.8251 (17)	0.1368 (15)	−0.2996 (10)	0.088*
H12B	0.9776 (17)	0.0569 (15)	−0.2974 (10)	0.088*
C13	1.0950 (14)	0.3039 (13)	−0.2039 (9)	0.059 (3)
H13A	1.2207 (14)	0.3046 (13)	−0.2243 (9)	0.071*
H13B	1.0706 (14)	0.3849 (13)	−0.2331 (9)	0.071*
S2	0.5347 (4)	0.2982 (3)	0.2382 (2)	0.0498 (5)
C21	0.3810 (13)	0.3629 (10)	0.3220 (7)	0.043 (2)
N21	0.3233 (12)	0.4730 (10)	0.3005 (7)	0.057 (2)
H21	0.3626 (12)	0.5212 (10)	0.2463 (7)	0.068*
N22	0.3032 (12)	0.3159 (10)	0.4129 (7)	0.056 (2)
H22	0.3249 (12)	0.2464 (10)	0.4417 (7)	0.067*
C22	0.1887 (16)	0.5032 (13)	0.3770 (9)	0.059 (3)
H22A	0.0618 (16)	0.4718 (13)	0.3345 (9)	0.070*
H22B	0.2379 (16)	0.6172 (13)	0.4197 (9)	0.070*
C23	0.1770 (14)	0.3954 (12)	0.4581 (10)	0.057 (3)
H23A	0.2241 (14)	0.4601 (12)	0.5380 (10)	0.069*
H23B	0.0438 (14)	0.3165 (12)	0.4548 (10)	0.069*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Au1	0.0468 (2)	0.0410 (2)	0.0439 (2)	0.0139 (2)	0.0090 (2)	0.0113 (2)
C1	0.056 (5)	0.042 (5)	0.041 (5)	0.019 (5)	0.011 (4)	0.015 (4)
N1	0.069 (6)	0.057 (5)	0.061 (5)	0.022 (5)	0.003 (4)	0.017 (4)
Au2	0.0454 (2)	0.0434 (2)	0.0417 (2)	0.0173 (2)	0.0073 (2)	0.0094 (2)
C2	0.077 (7)	0.064 (6)	0.045 (5)	0.041 (6)	0.028 (5)	0.024 (5)
N2	0.096 (7)	0.087 (7)	0.069 (6)	0.054 (6)	0.025 (5)	0.035 (6)
S1	0.0582 (15)	0.0517 (14)	0.0472 (13)	0.0030 (12)	0.0058 (11)	0.0053 (11)
C11	0.038 (4)	0.040 (5)	0.045 (5)	0.016 (4)	−0.003 (4)	0.001 (4)
N11	0.052 (4)	0.045 (4)	0.046 (4)	0.014 (4)	0.008 (4)	0.007 (4)
N12	0.049 (4)	0.042 (4)	0.060 (5)	0.004 (4)	0.007 (4)	0.013 (4)
C12	0.067 (7)	0.075 (8)	0.052 (6)	0.000 (6)	0.016 (5)	0.018 (6)
C13	0.050 (6)	0.067 (7)	0.058 (6)	0.013 (5)	0.009 (5)	0.031 (5)
S2	0.0591 (14)	0.0475 (13)	0.0454 (13)	0.0221 (11)	0.0150 (10)	0.0153 (10)
C21	0.047 (5)	0.033 (4)	0.042 (5)	0.009 (4)	0.001 (4)	0.009 (4)
N21	0.064 (5)	0.057 (5)	0.060 (5)	0.033 (4)	0.011 (4)	0.022 (4)
N22	0.072 (6)	0.054 (5)	0.055 (5)	0.034 (4)	0.016 (4)	0.022 (4)
C22	0.072 (7)	0.057 (6)	0.053 (6)	0.037 (6)	0.005 (5)	0.007 (5)
C23	0.045 (5)	0.053 (6)	0.071 (7)	0.020 (5)	0.011 (5)	0.010 (5)

Geometric parameters (Å, º)

Au1—Au2	3.1167 (10)	C12—H12B	0.97
Au1—S1	2.292 (3)	C13—H13A	0.97
Au2—S2	2.295 (3)	C13—H13B	0.97
Au1—C1	1.964 (10)	S2—C21	1.717 (9)
Au2—C2	1.968 (10)	C21—N22	1.318 (11)
C1—N1	1.117 (12)	C21—N21	1.322 (11)
C2—N2	1.133 (13)	N21—C22	1.427 (12)
S1—C11	1.703 (9)	N21—H21	0.86
C11—N12	1.314 (11)	N22—C23	1.442 (12)
C11—N11	1.318 (11)	N22—H22	0.86
N11—C12	1.463 (13)	C22—C23	1.523 (15)
N11—H11	0.86	C22—H22A	0.97
N12—C13	1.452 (13)	C22—H22B	0.97
N12—H12	0.86	C23—H23A	0.97
C12—C13	1.542 (14)	C23—H23B	0.97
C12—H12A	0.97
C1—Au1—S1	173.6 (3)	C12—C13—H13A	111.2 (6)
C1—Au1—Au2	92.8 (3)	N12—C13—H13B	111.2 (5)
S1—Au1—Au2	84.79 (8)	C12—C13—H13B	111.2 (6)
N1—C1—Au1	175.4 (9)	H13A—C13—H13B	109.1
C2—Au2—S2	179.6 (3)	C21—S2—Au2	106.1 (3)
C2—Au2—Au1	93.4 (3)	N22—C21—N21	109.9 (8)
S2—Au2—Au1	86.50 (6)	N22—C21—S2	128.2 (7)
N2—C2—Au2	177.8 (11)	N21—C21—S2	121.9 (7)
C11—S1—Au1	106.5 (3)	C21—N21—C22	112.7 (8)
N12—C11—N11	110.1 (8)	C21—N21—H21	123.6 (5)
N12—C11—S1	123.2 (7)	C22—N21—H21	123.6 (5)
N11—C11—S1	126.6 (7)	C21—N22—C23	111.7 (8)
C11—N11—C12	113.0 (8)	C21—N22—H22	124.2 (5)
C11—N11—H11	123.5 (5)	C23—N22—H22	124.2 (5)
C12—N11—H11	123.5 (5)	N21—C22—C23	102.5 (8)
C11—N12—C13	112.5 (8)	N21—C22—H22A	111.3 (5)
C11—N12—H12	123.8 (5)	C23—C22—H22A	111.3 (6)
C13—N12—H12	123.8 (5)	N21—C22—H22B	111.3 (5)
N11—C12—C13	101.3 (8)	C23—C22—H22B	111.3 (5)
N11—C12—H12A	111.5 (6)	H22A—C22—H22B	109.2
C13—C12—H12A	111.5 (6)	N22—C23—C22	103.1 (8)
N11—C12—H12B	111.5 (6)	N22—C23—H23A	111.1 (5)
C13—C12—H12B	111.5 (6)	C22—C23—H23A	111.1 (5)
H12A—C12—H12B	109.3	N22—C23—H23B	111.1 (5)
N12—C13—C12	103.0 (8)	C22—C23—H23B	111.1 (6)
N12—C13—H13A	111.2 (5)	H23A—C23—H23B	109.1
C1—Au1—Au2—C2	57.8 (4)	C11—N12—C13—C12	2.2 (12)
S1—Au1—Au2—C2	−116.2 (3)	N11—C12—C13—N12	−2.9 (11)
C1—Au1—Au2—S2	−122.5 (3)	N22—C21—N21—C22	−2.7 (11)
S1—Au1—Au2—S2	63.42 (10)	S2—C21—N21—C22	177.1 (7)
N12—C11—N11—C12	−1.8 (11)	N21—C21—N22—C23	1.4 (11)
S1—C11—N11—C12	−179.7 (8)	S2—C21—N22—C23	−178.4 (7)
N11—C11—N12—C13	−0.4 (11)	C21—N21—C22—C23	2.7 (11)
S1—C11—N12—C13	177.6 (7)	C21—N22—C23—C22	0.2 (10)
C11—N11—C12—C13	3.0 (12)	N21—C22—C23—N22	−1.7 (10)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N11—H11···S2^i	0.86	2.76	3.556 (8)	155
N12—H12···N1^ii	0.86	2.14	2.999 (12)	172
N21—H21···N1^iii	0.86	2.15	2.988 (12)	163
N22—H22···N2^iv	0.86	2.07	2.880 (13)	157

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

(II) 1,1-bis(dimethylthiourea)-2,2-dicyano-digold(I)

Crystal data

[Au2(CN)2(C3H8N2S)2]	F(000) = 1184
Mr = 654.32	Dx = 2.784 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 13.3922 (2) Å	Cell parameters from 2105 reflections
b = 7.8170 (1) Å	θ = 1.5–25.0°
c = 14.9588 (3) Å	µ = 19.03 mm^−1
β = 94.506 (1)°	T = 174 K
V = 1561.15 (4) Å^3	Needle, colorless
Z = 4	0.16 × 0.06 × 0.04 mm

Data collection

Siemens SMART area-detector diffractometer	2737 independent reflections
Radiation source: fine-focus sealed tube	2421 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.030
ω scans	θmax = 25.0°, θmin = 1.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996; Blessing, 1995)	h = −14→15
Tmin = 0.27, Tmax = 0.47	k = −9→8
7629 measured reflections	l = −17→17

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.026	Riding
wR(F^2) = 0.063	Calculated w = 1/[σ^2(Fo^2) + (0.033P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.07	(Δ/σ)max = 0.002
2737 reflections	Δρmax = 1.97 e Å^−3
168 parameters	Δρmin = −1.27 e Å^−3
0 restraints	Extinction correction: SHELXTL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.00035 (8)

Special details

Experimental. IR spectra were recorded as KBr pellets with a Perkin-Elmer Model 1430 spectrophotometer. Elemental analyses were determined by Galbraith Laboratries, Knoxville, TN.

Refinement. There are 15 peaks and valleys in the final difference map with magnitudes greater tan 0.75 e/Å₃. All of these are between 0.85 and 1.20 Å from one or the other of the Au atoms.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Au1	0.17096 (2)	0.21039 (3)	0.84800 (2)	0.02645 (11)
Au2	0.25436 (2)	0.54854 (3)	0.77682 (2)	0.02818 (11)
C1	0.2080 (5)	0.4932 (9)	0.6510 (5)	0.028 (2)
N1	0.1848 (5)	0.4559 (7)	0.5783 (4)	0.0347 (14)
C2	0.3083 (5)	0.6074 (10)	0.9003 (5)	0.033 (2)
N2	0.3401 (5)	0.6353 (10)	0.9699 (5)	0.046 (2)
S1	0.01648 (13)	0.3363 (2)	0.83774 (12)	0.0330 (4)
C11	−0.0413 (5)	0.3090 (8)	0.9363 (5)	0.0263 (15)
N12	−0.1300 (4)	0.3833 (7)	0.9412 (4)	0.0304 (13)
H12	−0.1585 (4)	0.3728 (7)	0.9905 (4)	0.036*
N13	−0.0009 (4)	0.2200 (7)	1.0057 (4)	0.0274 (13)
H13	0.0574 (4)	0.1757 (7)	1.0018 (4)	0.033*
C14	−0.1815 (6)	0.4795 (10)	0.8703 (6)	0.039 (2)
H14A	−0.1379 (13)	0.567 (4)	0.850 (2)	0.059*
H14B	−0.240 (2)	0.532 (5)	0.8918 (11)	0.059*
H14C	−0.201 (3)	0.4045 (14)	0.8213 (14)	0.059*
C15	−0.0503 (6)	0.1936 (9)	1.0880 (5)	0.034 (2)
H15A	−0.0066 (15)	0.131 (6)	1.1302 (13)	0.051*
H15B	−0.111 (2)	0.130 (6)	1.0749 (7)	0.051*
H15C	−0.066 (3)	0.3024 (9)	1.1132 (18)	0.051*
S2	0.32664 (14)	0.0946 (2)	0.83130 (13)	0.0356 (4)
C21	0.4014 (5)	0.1736 (8)	0.9230 (5)	0.030 (2)
N22	0.4935 (4)	0.2312 (7)	0.9107 (4)	0.0326 (14)
H22	0.5323 (4)	0.2556 (7)	0.9576 (4)	0.039*
N23	0.3699 (5)	0.1715 (8)	1.0041 (4)	0.0358 (15)
H23	0.3120 (5)	0.1278 (8)	1.0104 (4)	0.043*
C24	0.5328 (6)	0.2554 (11)	0.8228 (6)	0.046 (2)
H24A	0.546 (4)	0.1459 (12)	0.7970 (17)	0.070*
H24B	0.594 (2)	0.320 (6)	0.8298 (7)	0.070*
H24C	0.4846 (19)	0.316 (6)	0.7841 (13)	0.070*
C25	0.4256 (6)	0.2372 (10)	1.0835 (5)	0.036 (2)
H25A	0.3870 (16)	0.222 (6)	1.1343 (7)	0.054*
H25B	0.439 (3)	0.3566 (16)	1.0755 (13)	0.054*
H25C	0.4877 (17)	0.176 (4)	1.0932 (18)	0.054*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Au1	0.0246 (2)	0.0304 (2)	0.0245 (2)	−0.00517 (11)	0.00239 (11)	0.00145 (11)
Au2	0.0263 (2)	0.0316 (2)	0.0270 (2)	−0.00442 (11)	0.00412 (11)	−0.00039 (11)
C1	0.028 (4)	0.031 (4)	0.025 (4)	0.002 (3)	0.004 (3)	0.003 (3)
N1	0.035 (3)	0.037 (3)	0.033 (4)	0.006 (3)	0.005 (3)	0.000 (3)
C2	0.028 (4)	0.045 (4)	0.025 (4)	−0.007 (3)	−0.003 (3)	−0.007 (3)
N2	0.034 (4)	0.062 (4)	0.041 (5)	−0.005 (3)	0.007 (3)	0.001 (4)
S1	0.0293 (10)	0.0420 (10)	0.0278 (10)	0.0013 (8)	0.0039 (8)	0.0097 (8)
C11	0.024 (4)	0.021 (3)	0.033 (4)	−0.006 (3)	0.000 (3)	0.003 (3)
N12	0.029 (3)	0.031 (3)	0.032 (4)	0.004 (3)	0.008 (3)	0.005 (3)
N13	0.025 (3)	0.028 (3)	0.029 (3)	−0.001 (2)	0.004 (2)	0.003 (2)
C14	0.032 (4)	0.041 (4)	0.045 (5)	0.007 (4)	0.004 (4)	0.007 (4)
C15	0.042 (4)	0.035 (4)	0.024 (4)	0.004 (3)	0.003 (3)	0.002 (3)
S2	0.0300 (10)	0.0437 (10)	0.0325 (11)	0.0000 (8)	−0.0007 (8)	−0.0096 (8)
C21	0.029 (4)	0.029 (3)	0.033 (4)	0.003 (3)	0.005 (3)	0.002 (3)
N22	0.024 (3)	0.043 (3)	0.031 (4)	0.001 (3)	0.003 (3)	−0.001 (3)
N23	0.028 (3)	0.048 (4)	0.032 (4)	−0.009 (3)	0.006 (3)	0.000 (3)
C24	0.035 (5)	0.069 (5)	0.036 (5)	−0.007 (4)	0.010 (4)	−0.008 (4)
C25	0.037 (4)	0.051 (4)	0.020 (4)	−0.001 (4)	0.001 (3)	0.003 (3)

Geometric parameters (Å, º)

Au1—Au2	3.0911 (4)	C15—H15A	0.96
Au1—S1	2.285 (2)	C15—H15B	0.96
Au1—S2	2.304 (2)	C15—H15C	0.96
Au2—C1	1.983 (8)	S2—C21	1.746 (8)
Au2—C2	1.984 (8)	C21—N23	1.315 (9)
C1—N1	1.145 (9)	C21—N22	1.340 (9)
C2—N2	1.115 (9)	N22—C24	1.466 (9)
S1—C11	1.731 (7)	N22—H22	0.86
C11—N13	1.329 (9)	N23—C25	1.445 (10)
C11—N12	1.330 (8)	N23—H23	0.86
N12—C14	1.432 (10)	C24—H24A	0.96
N12—H12	0.86	C24—H24B	0.96
N13—C15	1.459 (9)	C24—H24C	0.96
N13—H13	0.86	C25—H25A	0.96
C14—H14A	0.96	C25—H25B	0.96
C14—H14B	0.96	C25—H25C	0.96
C14—H14C	0.96
S1—Au1—S2	169.70 (7)	H15A—C15—H15B	109.5
S1—Au1—Au2	87.61 (5)	N13—C15—H15C	109.5 (3)
S2—Au1—Au2	86.79 (5)	H15A—C15—H15C	109.5
C1—Au2—C2	176.7 (3)	H15B—C15—H15C	109.5
C1—Au2—Au1	92.6 (2)	C21—S2—Au1	104.1 (2)
C2—Au2—Au1	89.6 (2)	N23—C21—N22	119.7 (7)
N1—C1—Au2	176.9 (6)	N23—C21—S2	121.0 (5)
N2—C2—Au2	177.6 (7)	N22—C21—S2	119.2 (5)
C11—S1—Au1	110.6 (2)	C21—N22—C24	124.4 (7)
N13—C11—N12	119.7 (6)	C21—N22—H22	117.8 (4)
N13—C11—S1	123.2 (5)	C24—N22—H22	117.8 (4)
N12—C11—S1	117.1 (5)	C21—N23—C25	124.9 (6)
C11—N12—C14	124.6 (6)	C21—N23—H23	117.6 (4)
C11—N12—H12	117.7 (4)	C25—N23—H23	117.6 (4)
C14—N12—H12	117.7 (4)	N22—C24—H24A	109.5 (4)
C11—N13—C15	123.4 (6)	N22—C24—H24B	109.5 (4)
C11—N13—H13	118.3 (4)	H24A—C24—H24B	109.5
C15—N13—H13	118.3 (4)	N22—C24—H24C	109.5 (4)
N12—C14—H14A	109.5 (4)	H24A—C24—H24C	109.5
N12—C14—H14B	109.5 (4)	H24B—C24—H24C	109.5
H14A—C14—H14B	109.5	N23—C25—H25A	109.5 (4)
N12—C14—H14C	109.5 (4)	N23—C25—H25B	109.5 (4)
H14A—C14—H14C	109.5	H25A—C25—H25B	109.5
H14B—C14—H14C	109.5	N23—C25—H25C	109.5 (4)
N13—C15—H15A	109.5 (4)	H25A—C25—H25C	109.5
N13—C15—H15B	109.5 (4)	H25B—C25—H25C	109.5
S1—Au1—Au2—C1	−79.5 (2)	S1—Au1—Au2—C2	102.9 (2)
S2—Au1—Au2—C1	91.8 (2)	S2—Au1—Au2—C2	−85.7 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N12—H12···N2^i	0.86	2.55	3.207 (8)	134
N13—H13···N1^ii	0.86	2.23	2.972 (9)	144
N22—H22···N2^iii	0.86	2.13	2.936 (10)	156
N23—H23···N1^ii	0.86	2.15	2.968 (8)	158

Symmetry codes: (i) −x, −y+1, −z+2; (ii) x, −y+1/2, z+1/2; (iii) −x+1, −y+1, −z+2.