Dichlorido(4,4′-di-tert-butyl-2,2′-bi­pyridine-κ2N,N′)gold(III) tetrachlorido­aurate(III) acetonitrile solvate

Yıldırım, S.Ö.; Akkurt, M.; Safari, N.; Amani, V.; McKee, V.; Abedi, A.; Khavasi, H.R.

doi:10.1107/S1600536808025646

metal-organic compounds

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ISSN: 2056-9890

Volume 64| Part 9| September 2008| Pages m1189-m1190

doi:10.1107/S1600536808025646

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Dichlorido(4,4′-di-tert-butyl-2,2′-bipyridine-κ²N,N′)gold(III) tetrachloridoaurate(III) acetonitrile solvate

Sema Öztürk Yıldırım,^a Mehmet Akkurt,^a ^* Nasser Safari,^b Vahid Amani,^b Vickie McKee,^c Anita Abedi ^d and Hamid Reza Khavasi ^b

^aDepartment of Physics, Faculty of Arts and Sciences, Erciyes University, 38039 Kayseri, Turkey, ^bChemistry Department, Shahid Beheshti University, Evin, Tehran 1983963113, Iran, ^cDepartment of Chemistry, Loughborough University, Leicestershire LE11 3TU, England, and ^dDepartment of Chemistry, North Tehran Branch, Islamic Azad University, Tehran, Iran
^*Correspondence e-mail: akkurt@erciyes.edu.tr

(Received 7 August 2008; accepted 8 August 2008; online 20 August 2008)

In the title compound, [AuCl₂(C₉H₁₂N)₂][AuCl₄]·C₂H₃N, there is a mirror plane passing through Au and the central C—C bond of the bipyridyl ligand in the cation, and through Au and two Cl atoms of the anion. A cis-AuCl₂N₂ square-planar geometry for the cation and a square-planar AuCl₄ geometry for the anion result. The two C atoms and the N atom of the acetonitrile molecule all have m site symmetries. In the crystal structure, weak C—H⋯Cl interactions may help to establish the packing.

Related literature

For related structures, see: Abbate et al. (2000 ); Adams & Strähle (1982 ); Bjernemose et al. (2004 ); Hayoun et al. (2006 ); McInnes et al. (1995 ).

Experimental

Crystal data

[AuCl₂(C₉H₁₂N)₂][AuCl₄]·C₂H₃N
M_r = 916.09
Monoclinic, P 2₁ /m
a = 6.7880 (9) Å
b = 14.2270 (19) Å
c = 14.1330 (19) Å
β = 97.151 (2)°
V = 1354.3 (3) Å³
Z = 2
Mo Kα radiation
μ = 11.43 mm⁻¹
T = 150 (2) K
0.14 × 0.10 × 0.01 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2003 ) T_min = 0.298, T_max = 0.894
14949 measured reflections
3888 independent reflections
2860 reflections with I > 2σ(I)
R_int = 0.060

Refinement

R[F² > 2σ(F²)] = 0.036
wR(F²) = 0.079
S = 1.01
3888 reflections
155 parameters
H-atom parameters constrained
Δρ_max = 1.59 e Å⁻³
Δρ_min = −1.24 e Å⁻³

Table 1
Selected geometric parameters (Å, °)

Au1—Cl1	2.2590 (17)
Au1—N1	2.020 (4)
Au2—Cl2	2.271 (2)
Au2—Cl3	2.2675 (16)
Au2—Cl4	2.311 (2)

N2—C11—C10	179.5 (14)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯Cl3ⁱ	0.93	2.66	3.561 (6)	162
C3—H3⋯Cl1ⁱⁱ	0.93	2.64	3.231 (6)	122
Symmetry codes: (i) -x+1, -y+1, -z; (ii) $[x, -y+{\script{1\over 2}}, z]$ .

Data collection: APEX2 (Bruker, 2005 ); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SIR92 (Altomare et al., 1993 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: ORTEP-3 (Farrugia, 1997 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808025646/hb2776sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808025646/hb2776Isup2.hkl

checkCIF report

Comment top

Several Au^III complexes, with formula, [AuCl₂(N—N)], such as [AuCl₂(bipy)][BF₄], (II), (McInnes et al., 1995), [AuCl₂(bipy)](NO₃), (III), (Bjernemose et al., 2004), [AuCl₂(bipy)][AuBr₄], (IV), (Hayoun et al., 2006) and [AuCl₂(phen)]Cl.H₂O, (V), (Abbate et al., 2000) [where bipy is 2,2'-bipyridine and phen is 1,10-phenanthroline] have been synthesized and characterized by single-crystal X-ray diffraction methods.

Other Au^III complexes, with formula, [AuCl₂L₂], such as [AuCl₂(py)₂][AuCl₄], (VI) and [AuCl₂(py)₂]Cl.H₂O, (VII), (Adams & Strähle 1982) [where py is pyridine] have also bee prepared and characterized. We report herein the synthesis and crystal structure of the title compound, (I).

The asymmetric unit of (I) (Fig. 1) contains one half-cation, one half-anion and one half-acetonitrile molecule; the whole assemblage is symmetric according to a mirror plane. Both Au ions have square-planar coordination (Table 1) and the individual bond lengths and angles are in good agreement with the corresponding values in (II), (III), (IV), (V), (VI) and (VII).

In the crystal of (I), weak intermolecular C—H···Cl hydrogen bonds (Table 2) link the molecules to form a supramolecular structure (Fig. 2 and Fig. 3).

Related literature top

For related structures, see: Abbate et al. (2000); Adams & Strähle (1982); Bjernemose et al. (2004); Hayoun et al. (2006); McInnes et al. (1995).

Experimental top

A solution of 4,4'-di-tert-butyl-2,2'-bipyridine (0.15 g, 0.56 mmol) in acetonitrile (40 ml) was added to a solution of HAuCl₄.3H₂O, (0.22 g, 0.56 mmol) in EtOH (50 ml) and the resulting yellow solution was stirred for 10 min at 313 K. Then, it was left to evaporate slowly at room temperature. After one week, yellow laths and prisms of (I) were isolated (yield 0.38 g; 74.0%).

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

	Fig. 1. View of the molecular structure of (I) with displacement ellipsoids for non-H atoms drawn at the 30% probability level and H atoms omitted for clarity. The symmetry codes a and b both refer to (x, 1/2 - y, z).
	Fig. 2. A view of the packing and the hydrogen bonding (dashed lines) of (I) down the a axis in the unit cell.
	Fig. 3. View of the unit-cell packing of (I) down the c axis.

Dichlorido(4,4'-di-tert-butyl-2,2'-bipyridine- κ²N,N')gold(III) tetrachloroaurate(III) acetonitrile solvate top

Crystal data top

[AuCl₂(C₉H₁₂N)₂][AuCl₄]·C₂H₃N	F(000) = 856
M_r = 916.09	D_x = 2.247 Mg m⁻³
Monoclinic, P2₁/m	Mo Kα radiation, λ = 0.71069 Å
Hall symbol: -P 2yb	Cell parameters from 2450 reflections
a = 6.7880 (9) Å	θ = 2.9–24.8°
b = 14.2270 (19) Å	µ = 11.43 mm⁻¹
c = 14.1330 (19) Å	T = 150 K
β = 97.151 (2)°	Lath, yellow
V = 1354.3 (3) Å³	0.14 × 0.10 × 0.01 mm
Z = 2

Data collection top

Bruker APEXII CCD diffractometer	3888 independent reflections
Radiation source: sealed tube	2860 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.060
ϕ and ω scans	θ_max = 29.5°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	h = −9→9
T_min = 0.298, T_max = 0.894	k = −19→19
14949 measured reflections	l = −19→18

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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.079	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.0318P)²] where P = (F_o² + 2F_c²)/3
3888 reflections	(Δ/σ)_max < 0.001
155 parameters	Δρ_max = 1.60 e Å⁻³
0 restraints	Δρ_min = −1.24 e Å⁻³

Crystal data top

[AuCl₂(C₉H₁₂N)₂][AuCl₄]·C₂H₃N	V = 1354.3 (3) Å³
M_r = 916.09	Z = 2
Monoclinic, P2₁/m	Mo Kα radiation
a = 6.7880 (9) Å	µ = 11.43 mm⁻¹
b = 14.2270 (19) Å	T = 150 K
c = 14.1330 (19) Å	0.14 × 0.10 × 0.01 mm
β = 97.151 (2)°

Data collection top

Bruker APEXII CCD diffractometer	3888 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	2860 reflections with I > 2σ(I)
T_min = 0.298, T_max = 0.894	R_int = 0.060
14949 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.036	0 restraints
wR(F²) = 0.079	H-atom parameters constrained
S = 1.01	Δρ_max = 1.60 e Å⁻³
3888 reflections	Δρ_min = −1.24 e Å⁻³
155 parameters

Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F² for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The observed criterion of F² > σ(F²) is used only for calculating -R-factor-obs 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	Occ. (<1)
Au1	0.23789 (4)	0.25000	−0.04727 (2)	0.0241 (1)
Cl1	0.2075 (2)	0.13933 (12)	−0.16278 (11)	0.0366 (5)
N1	0.2670 (6)	0.3421 (3)	0.0624 (3)	0.0238 (14)
C1	0.3143 (8)	0.3571 (4)	0.2320 (4)	0.0258 (17)
C2	0.2920 (7)	0.3000 (4)	0.1509 (4)	0.0222 (16)
C3	0.2636 (8)	0.4365 (4)	0.0544 (4)	0.0286 (17)
C4	0.2861 (8)	0.4940 (4)	0.1338 (4)	0.0303 (17)
C5	0.3113 (8)	0.4559 (4)	0.2252 (4)	0.0277 (17)
C6	0.3361 (8)	0.5158 (4)	0.3150 (4)	0.0287 (17)
C7	0.5416 (9)	0.4930 (4)	0.3701 (4)	0.0345 (19)
C8	0.1694 (9)	0.4913 (4)	0.3758 (4)	0.0333 (19)
C9	0.3254 (9)	0.6207 (4)	0.2926 (5)	0.035 (2)
N2	0.3784 (17)	0.25000	0.4696 (8)	0.066 (4)
C10	0.104 (2)	0.25000	0.5775 (11)	0.087 (6)
C11	0.2608 (17)	0.25000	0.5153 (9)	0.049 (4)
Au2	0.79109 (4)	0.25000	0.14539 (2)	0.0258 (1)
Cl2	0.8353 (4)	0.25000	0.30734 (16)	0.0402 (8)
Cl3	0.7908 (2)	0.40938 (11)	0.14566 (12)	0.0363 (5)
Cl4	0.7455 (3)	0.25000	−0.01937 (17)	0.0364 (7)
H1	0.33140	0.32920	0.29200	0.0310*
H3	0.24570	0.46360	−0.00600	0.0340*
H4	0.28430	0.55890	0.12610	0.0360*
H7A	0.64220	0.50110	0.32870	0.0520*
H7B	0.54290	0.42920	0.39220	0.0520*
H7C	0.56740	0.53460	0.42370	0.0520*
H8A	0.18300	0.52950	0.43220	0.0500*
H8B	0.17890	0.42610	0.39360	0.0500*
H8C	0.04260	0.50290	0.33950	0.0500*
H9A	0.43180	0.63750	0.25710	0.0520*
H9B	0.33720	0.65570	0.35110	0.0520*
H9C	0.20060	0.63480	0.25560	0.0520*
H10A	0.07320	0.18640	0.59320	0.1300*	0.500
H10B	−0.01270	0.27970	0.54530	0.1300*	0.500
H10C	0.14820	0.28390	0.63500	0.1300*	0.500

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Au1	0.0226 (2)	0.0279 (2)	0.0216 (2)	0.0000	0.0016 (1)	0.0000
Cl1	0.0483 (9)	0.0351 (8)	0.0257 (8)	0.0000 (7)	0.0023 (7)	−0.0050 (7)
N1	0.023 (2)	0.024 (2)	0.024 (3)	−0.0009 (19)	0.0014 (19)	−0.003 (2)
C1	0.023 (3)	0.025 (3)	0.029 (3)	0.002 (2)	0.002 (2)	0.004 (2)
C2	0.014 (2)	0.038 (3)	0.015 (3)	0.000 (2)	0.003 (2)	0.001 (2)
C3	0.033 (3)	0.029 (3)	0.024 (3)	−0.001 (3)	0.004 (2)	0.002 (3)
C4	0.032 (3)	0.025 (3)	0.033 (3)	−0.001 (2)	0.000 (3)	0.000 (3)
C5	0.021 (3)	0.032 (3)	0.031 (3)	−0.001 (2)	0.007 (2)	−0.001 (3)
C6	0.029 (3)	0.024 (3)	0.032 (3)	0.005 (2)	0.000 (3)	−0.002 (3)
C7	0.036 (3)	0.036 (4)	0.030 (3)	0.002 (3)	−0.002 (3)	−0.006 (3)
C8	0.034 (3)	0.035 (4)	0.031 (3)	−0.002 (3)	0.004 (3)	−0.007 (3)
C9	0.036 (3)	0.035 (4)	0.032 (4)	−0.001 (3)	−0.001 (3)	−0.003 (3)
N2	0.081 (8)	0.053 (6)	0.068 (7)	0.0000	0.020 (6)	0.0000
C10	0.109 (12)	0.079 (10)	0.080 (10)	0.0000	0.043 (9)	0.0000
C11	0.061 (7)	0.035 (6)	0.051 (7)	0.0000	0.012 (6)	0.0000
Au2	0.0194 (2)	0.0261 (2)	0.0318 (2)	0.0000	0.0033 (1)	0.0000
Cl2	0.0509 (14)	0.0399 (13)	0.0290 (12)	0.0000	0.0018 (10)	0.0000
Cl3	0.0365 (8)	0.0275 (8)	0.0448 (10)	−0.0009 (6)	0.0046 (7)	0.0040 (7)
Cl4	0.0272 (10)	0.0439 (13)	0.0377 (12)	0.0000	0.0022 (9)	0.0000

Geometric parameters (Å, º) top

Au1—Cl1	2.2590 (17)	C1—H1	0.9300
Au1—N1	2.020 (4)	C3—H3	0.9300
Au1—Cl1ⁱ	2.2590 (17)	C4—H4	0.9300
Au1—N1ⁱ	2.020 (4)	C7—H7B	0.9600
Au2—Cl2	2.271 (2)	C7—H7A	0.9600
Au2—Cl3	2.2675 (16)	C7—H7C	0.9600
Au2—Cl4	2.311 (2)	C8—H8A	0.9600
Au2—Cl3ⁱ	2.2675 (16)	C8—H8C	0.9600
N1—C3	1.348 (7)	C8—H8B	0.9600
N1—C2	1.378 (7)	C9—H9B	0.9600
N2—C11	1.088 (17)	C9—H9C	0.9600
C1—C5	1.409 (8)	C9—H9A	0.9600
C1—C2	1.398 (8)	C10—C11	1.462 (19)
C2—C2ⁱ	1.423 (8)	C10—H10Bⁱ	0.9600
C3—C4	1.382 (8)	C10—H10Cⁱ	0.9600
C4—C5	1.392 (8)	C10—H10Aⁱ	0.9600
C5—C6	1.521 (8)	C10—H10A	0.9600
C6—C8	1.544 (8)	C10—H10B	0.9600
C6—C9	1.526 (8)	C10—H10C	0.9600
C6—C7	1.545 (8)

Cl1—Au1—N1	176.24 (13)	H7A—C7—H7C	109.00
Cl1—Au1—Cl1ⁱ	88.38 (6)	C6—C7—H7C	109.00
Cl1—Au1—N1ⁱ	95.38 (13)	H7A—C7—H7B	109.00
Cl1ⁱ—Au1—N1	95.38 (13)	H7B—C7—H7C	109.00
N1—Au1—N1ⁱ	80.86 (17)	C6—C8—H8C	110.00
Cl1ⁱ—Au1—N1ⁱ	176.24 (13)	C6—C8—H8A	109.00
Cl2—Au2—Cl3ⁱ	89.91 (4)	C6—C8—H8B	109.00
Cl2—Au2—Cl3	89.91 (4)	H8A—C8—H8B	109.00
Cl2—Au2—Cl4	179.90 (8)	H8A—C8—H8C	109.00
Cl3ⁱ—Au2—Cl4	90.10 (4)	H8B—C8—H8C	109.00
Cl3—Au2—Cl4	90.10 (4)	H9A—C9—H9B	109.00
Cl3—Au2—Cl3ⁱ	179.77 (6)	H9A—C9—H9C	110.00
Au1—N1—C2	113.8 (3)	H9B—C9—H9C	110.00
Au1—N1—C3	125.7 (4)	C6—C9—H9A	109.00
C2—N1—C3	120.5 (5)	C6—C9—H9B	109.00
C2—C1—C5	121.7 (5)	C6—C9—H9C	109.00
C1—C2—C2ⁱ	125.5 (5)	N2—C11—C10	179.5 (14)
N1—C2—C2ⁱ	115.8 (5)	C11—C10—H10Cⁱ	110.00
N1—C2—C1	118.7 (5)	C11—C10—H10A	110.00
N1—C3—C4	121.5 (5)	C11—C10—H10B	110.00
C3—C4—C5	120.8 (5)	C11—C10—H10C	110.00
C1—C5—C6	120.2 (5)	C11—C10—H10Aⁱ	110.00
C1—C5—C4	116.8 (5)	C11—C10—H10Bⁱ	110.00
C4—C5—C6	123.0 (5)	H10Aⁱ—C10—H10B	60.00
C8—C6—C9	108.5 (5)	H10B—C10—H10Bⁱ	52.00
C5—C6—C7	107.6 (4)	H10B—C10—H10Cⁱ	141.00
C5—C6—C8	109.0 (5)	H10Aⁱ—C10—H10C	52.00
C5—C6—C9	112.2 (5)	H10Bⁱ—C10—H10C	141.00
C7—C6—C8	110.5 (5)	H10C—C10—H10Cⁱ	60.00
C7—C6—C9	109.1 (5)	H10Aⁱ—C10—H10Bⁱ	109.00
C5—C1—H1	119.00	H10Aⁱ—C10—H10Cⁱ	109.00
C2—C1—H1	119.00	H10Bⁱ—C10—H10Cⁱ	109.00
N1—C3—H3	119.00	H10A—C10—H10B	109.00
C4—C3—H3	119.00	H10A—C10—H10C	109.00
C5—C4—H4	120.00	H10A—C10—H10Aⁱ	141.00
C3—C4—H4	120.00	H10A—C10—H10Bⁱ	60.00
C6—C7—H7B	109.00	H10A—C10—H10Cⁱ	52.00
C6—C7—H7A	109.00	H10B—C10—H10C	109.00

Cl1ⁱ—Au1—N1—C2	−179.5 (3)	N1—C2—C2ⁱ—N1ⁱ	0.0 (6)
Cl1ⁱ—Au1—N1—C3	0.5 (4)	N1—C2—C2ⁱ—C1ⁱ	−179.8 (5)
N1ⁱ—Au1—N1—C2	0.5 (3)	C1—C2—C2ⁱ—N1ⁱ	179.8 (5)
N1ⁱ—Au1—N1—C3	−179.6 (4)	C1—C2—C2ⁱ—C1ⁱ	0.0 (8)
Au1—N1—C2—C1	179.8 (4)	N1—C3—C4—C5	−0.6 (8)
Au1—N1—C2—C2ⁱ	−0.4 (5)	C3—C4—C5—C1	0.6 (8)
C3—N1—C2—C1	−0.2 (7)	C3—C4—C5—C6	−179.8 (5)
C3—N1—C2—C2ⁱ	179.6 (5)	C1—C5—C6—C7	60.9 (6)
Au1—N1—C3—C4	−179.6 (4)	C1—C5—C6—C8	−58.9 (7)
C2—N1—C3—C4	0.4 (8)	C1—C5—C6—C9	−179.1 (5)
C5—C1—C2—N1	0.2 (8)	C4—C5—C6—C7	−118.7 (6)
C5—C1—C2—C2ⁱ	−179.6 (5)	C4—C5—C6—C8	121.4 (6)
C2—C1—C5—C4	−0.3 (8)	C4—C5—C6—C9	1.3 (8)
C2—C1—C5—C6	−180.0 (5)

Symmetry code: (i) x, −y+1/2, z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···Cl3ⁱⁱ	0.93	2.66	3.561 (6)	162
C3—H3···Cl1ⁱ	0.93	2.64	3.231 (6)	122

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

Experimental details

Crystal data
Chemical formula	[AuCl₂(C₉H₁₂N)₂][AuCl₄]·C₂H₃N
M_r	916.09
Crystal system, space group	Monoclinic, P2₁/m
Temperature (K)	150
a, b, c (Å)	6.7880 (9), 14.2270 (19), 14.1330 (19)
β (°)	97.151 (2)
V (Å³)	1354.3 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	11.43
Crystal size (mm)	0.14 × 0.10 × 0.01

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2003)
T_min, T_max	0.298, 0.894
No. of measured, independent and observed [I > 2σ(I)] reflections	14949, 3888, 2860
R_int	0.060
(sin θ/λ)_max (Å⁻¹)	0.692

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.036, 0.079, 1.01
No. of reflections	3888
No. of parameters	155
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.60, −1.24

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SIR92 (Altomare et al., 1993), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), WinGX (Farrugia, 1999).

Selected geometric parameters (Å, º) top

Au1—Cl1	2.2590 (17)	Au2—Cl3	2.2675 (16)
Au1—N1	2.020 (4)	Au2—Cl4	2.311 (2)
Au2—Cl2	2.271 (2)

N2—C11—C10	179.5 (14)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···Cl3ⁱ	0.93	2.66	3.561 (6)	162
C3—H3···Cl1ⁱⁱ	0.93	2.64	3.231 (6)	122

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

Acknowledgements

We are grateful to Shahid Beheshti University and Islamic Azad University, North Tehran Branch, for financial support.

References

Abbate, F., Orioli, P., Bruni, B., Marcon, G. & Messori, L. (2000). Inorg. Chim. Acta, 311, 1–5. Web of Science CSD CrossRef CAS Google Scholar
Adams, H. N. & Strähle, J. (1982). Z. Anorg. Allg. Chem. 485, 65–80. CSD CrossRef CAS Web of Science Google Scholar
Altomare, A., Cascarano, G., Giacovazzo, C. & Guagliardi, A. (1993). J. Appl. Cryst. 26, 343–350. CrossRef Web of Science IUCr Journals Google Scholar
Bjernemose, J. K., Raithby, P. R. & Toftlund, H. (2004). Acta Cryst. E60, m1719–m1721. Web of Science CSD CrossRef IUCr Journals Google Scholar
Bruker (2005). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838. CrossRef CAS IUCr Journals Google Scholar
Hayoun, R., Zhong, D. K., Rheingold, A. L. & Doerrer, L. H. (2006). Inorg. Chem. 45, 6120–6122. Web of Science CSD CrossRef PubMed CAS Google Scholar
McInnes, E. J. L., Welch, A. J. & Yellowlees, L. J. (1995). Acta Cryst. C51, 2023–2025. CSD CrossRef CAS Web of Science IUCr Journals Google Scholar
Sheldrick, G. M. (2003). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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