Bis[dichlorido(5,5′-dimethyl-2,2′-bi­pyridine-κ2N,N′)gold(III)] tetra­chlorido­aurate(III) dichloridooaurate(I)

Karaca, S.; Akkurt, M.; Safari, N.; Amani, V.; Büyükgüngör, O.; Abedi, A.

doi:10.1107/S1600536809006436

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 3| March 2009| Pages m335-m336

doi:10.1107/S1600536809006436

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Bis[dichlorido(5,5′-dimethyl-2,2′-bipyridine-κ²N,N′)gold(III)] tetrachloridoaurate(III) dichloridooaurate(I)

Selvi Karaca,^a Mehmet Akkurt,^a ^* Nasser Safari,^b Vahid Amani,^b Orhan Büyükgüngör ^c and Anita Abedi ^d

^aDepartment of Physics, Faculty of Arts and Sciences, Erciyes University, 38039 Kayseri, Turkey, ^bChemistry Department, Shahid Beheshti University, GC, Tehran, Iran, ^cDepartment of Physics, Faculty of Arts and Sciences, Ondokuz Mayıs University, 55139 Samsun, Turkey, and ^dDepartment of Chemistry, North Tehran Branch, Islamic Azad University, Tehran, Iran
^*Correspondence e-mail: akkurt@erciyes.edu.tr

(Received 21 January 2009; accepted 21 February 2009; online 28 February 2009)

The title compound, [Au^IIICl₂(C₁₂H₁₂N₂)]₂[Au^IIICl₄][Au^ICl₂], contains three distinct types of Au atom. In the cation, the Au^III atom is four-coordinated in a distorted square-planar arrangement by an N,N′-bidentate 5,5′-dimethyl-2,2′-bipyridine ligand and two terminal Cl atoms. In the [AuCl₄]⁻ anion, the centrosymmetric Au^III atom has a square-planar coordination. The centrosymmetric [AuCl₂]⁻ anion is linear. Intra- and intermolecular C—H⋯Cl hydrogen bonds help to establish the conformation and packing.

Related literature

For related stuctures, see: Abbate et al. (2000 ); Adams & Strähle (1982 ); Ahmadi, Amani & Khavasi (2008 ); Ahmadi, Dehghan, Amani & Khavasi (2008 ); Bjernemose et al. (2004 ); Hayoun et al. (2006 ); Hollis & Lippard (1983 ); McInnes et al. (1995 ); Yıldırım et al. (2008 ).

Experimental

Crystal data

[AuCl₂(C₁₂H₁₂N₂)]₂[AuCl₄][AuCl₂]
M_r = 1510.86
Triclinic, $[P \overline 1]$
a = 9.0698 (4) Å
b = 10.0886 (4) Å
c = 11.1678 (5) Å
α = 91.155 (4)°
β = 108.148 (4)°
γ = 111.344 (3)°
V = 894.09 (7) Å³
Z = 1
Mo Kα radiation
μ = 17.13 mm⁻¹
T = 295 K
0.41 × 0.28 × 0.08 mm

Data collection

Stoe IPDS-2 diffractometer
Absorption correction: integration (X-RED32; Stoe & Cie, 2002 ) T_min = 0.054, T_max = 0.341
9898 measured reflections
3651 independent reflections
3193 reflections with I > 2σ(I)
R_int = 0.059

Refinement

R[F² > 2σ(F²)] = 0.042
wR(F²) = 0.112
S = 1.05
3651 reflections
191 parameters
H-atom parameters constrained
Δρ_max = 1.64 e Å⁻³
Δρ_min = −1.91 e Å⁻³

Table 1
Selected bond lengths (Å)

Au1—N1	2.028 (9)
Au1—N2	2.027 (7)
Au1—Cl1	2.252 (3)
Au1—Cl2	2.262 (3)
Au2—Cl3	2.246 (5)
Au2—Cl4	2.261 (3)
Au3—Cl5	2.248 (3)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1⋯Cl1	0.93	2.59	3.203 (11)	124
C8—H8⋯Cl2ⁱ	0.93	2.75	3.666 (12)	169
C11—H11⋯Cl2	0.93	2.64	3.233 (11)	122
Symmetry code: (i) x-1, y, z.

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SIR97 (Altomare et al., 1999 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809006436/hb2902sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809006436/hb2902Isup2.hkl

checkCIF report

Comment top

Recently, we reported the synthesis and crystal structure of the [Au(dtbpy)Cl₂][AuCl₄].CH₃CN, (II), (Yıldırım et al., 2008) [where dtbpy is 4,4'-di-tert-butyl-2,2'-bipyridine]. There are several Au^III complexes, with formula, [AuCl₂ (N—N)]X, such as [AuCl₂(bipy)][BF₄], (III), (McInnes et al., 1995), [AuCl₂(bipy)](NO₃), (IV), (Bjernemose et al., 2004), [AuCl₂(bipy)][AuBr₄], (V), (Hayoun et al., 2006), [AuCl₂(dmphen)][AuCl₄], (VI), (Ahmadi, Amani et al., 2008) and [AuCl₂ (phen)]Cl.H₂O, (VII), (Abbate et al., 2000) [where bipy is 2,2'-bipyridine, dmphen is 4,7-diphenyl-1,10-phenanthroline and phen is 1,10-phenanthroline] have been synthesized and characterized by single-crystal X-ray diffraction methods. Two Au^III complexes with formula, [AuCl₂L₂]X, [AuCl₂(py)₂][AuCl₄], (VIII), and [AuCl₂(py)₂]Cl.H₂O, (IX), (Adams & Strähle 1982) [py is pyridine] and two mixed-valence Au^I—Au^III complexes, [Au(terpy)Cl]₂[AuCl₂]₃[AuCl₄], (X), (Hollis & Lippard, 1983) and [Au(dmpy)₂][AuCl₄], (XI), (Ahmadi, Dehghan et al., 2008) [where terpy is 2,2',2''-terpyridine and dmpy is 2,6-dimethylpyridine] have been synthesized and characterized by single-crystal X-ray diffraction methods. We report herein the synthesis and crystal structure of the title compound (I).

In the asymmetric unit of the title compound (I), (Fig. 1), there are one cation and two half-anions. In the cation, the Au^III atom is four-coordinated in a distorted square-planar configuration by two N atoms from the ligand and two terminal Cl atoms. In the anion AuCl₄, the Au^III atom has a square-planar coordination. The anion AuCl₂ is linear. In the cation, the Au—Cl and Au—N bond lengths and angles (Table 1) are in good agreement with the corresponding values in (II), (III), (IV), (V), (VI), (VII), (VIII), (IX), (X) and, (XI). In the anion, the Au—Cl bond lengths and angles (Table 1) are normal.

Intra and intermolecular C—H···Cl hydrogen bonding interactions (Table 2) stabilize the molecular conformation and the packing arrangement (Fig. 2).

Related literature top

For related stuctures, see: Abbate et al. (2000); Adams & Strähle (1982); Ahmadi, Amani & Khavasi (2008); Ahmadi, Dehghan, Amani & Khavasi (2008); Bjernemose et al. (2004); Hayoun et al. (2006); Hollis & Lippard (1983); McInnes et al. (1995); Yıldırım et al. (2008).

Experimental top

A solution of 5,5'-dimethyl-2,2'-bipyridine (0.20 g, 1.09 mmol) in ethanol (20 ml) was added to a solution of HAuCl₃.3H₂O, (0.37 g, 1.09 mmol) in acetonitrile (20 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 prismatic crystals of (I) were isolated (yield 0.28 g, 72.8%; m.p. 553 K).

Computing details top

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA (Stoe & Cie, 2002); data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

	Fig. 1. The molecular structure of (I) showing 50% probability displacement ellipsoids for the non-hydrogen atoms. Symmetry code suffixes: (a) –x, –y, –z; (b) 2–x, 1–y, 1–z.
	Fig. 2. A general view of the packing and hydrogen bonding interactions in (I).

Bis[dichlorido(5,5'-dimethyl-2,2'-bipyridine-κ²N,N')gold(III)] tetrachloridoaurate(III) dichloridooaurate(I) top

Crystal data top

[AuCl₂(C₁₂H₁₂N₂)]₂[AuCl₄][AuCl₂]	Z = 1
M_r = 1510.86	F(000) = 682
Triclinic, P1	D_x = 2.806 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.0698 (4) Å	Cell parameters from 16778 reflections
b = 10.0886 (4) Å	θ = 1.9–28.0°
c = 11.1678 (5) Å	µ = 17.13 mm⁻¹
α = 91.155 (4)°	T = 295 K
β = 108.148 (4)°	Prism, yellow
γ = 111.344 (3)°	0.41 × 0.28 × 0.08 mm
V = 894.09 (7) Å³

Data collection top

Stoe IPDS-2 diffractometer	3651 independent reflections
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus	3193 reflections with I > 2σ(I)
Plane graphite monochromator	R_int = 0.059
Detector resolution: 6.67 pixels mm^-1	θ_max = 26.5°, θ_min = 1.9°
ω scans	h = −10→11
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	k = −12→12
T_min = 0.054, T_max = 0.341	l = −14→14
9898 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.042	H-atom parameters constrained
wR(F²) = 0.112	w = 1/[σ²(F_o²) + (0.0703P)² + 0.309P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max = 0.001
3651 reflections	Δρ_max = 1.64 e Å⁻³
191 parameters	Δρ_min = −1.91 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=KFc[1+0.001XFc²Λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0042 (5)

Crystal data top

[AuCl₂(C₁₂H₁₂N₂)]₂[AuCl₄][AuCl₂]	γ = 111.344 (3)°
M_r = 1510.86	V = 894.09 (7) Å³
Triclinic, P1	Z = 1
a = 9.0698 (4) Å	Mo Kα radiation
b = 10.0886 (4) Å	µ = 17.13 mm⁻¹
c = 11.1678 (5) Å	T = 295 K
α = 91.155 (4)°	0.41 × 0.28 × 0.08 mm
β = 108.148 (4)°

Data collection top

Stoe IPDS-2 diffractometer	3651 independent reflections
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	3193 reflections with I > 2σ(I)
T_min = 0.054, T_max = 0.341	R_int = 0.059
9898 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	0 restraints
wR(F²) = 0.112	H-atom parameters constrained
S = 1.05	Δρ_max = 1.64 e Å⁻³
3651 reflections	Δρ_min = −1.91 e Å⁻³
191 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
Au1	1.23403 (3)	0.77774 (3)	0.26312 (3)	0.0544 (1)
Cl1	1.2859 (3)	0.5914 (3)	0.1987 (3)	0.0790 (9)
Cl2	1.5117 (3)	0.9173 (3)	0.3196 (3)	0.0782 (9)
N1	0.9831 (9)	0.6658 (8)	0.2201 (7)	0.060 (2)
N2	1.1693 (8)	0.9371 (7)	0.3140 (6)	0.0528 (19)
C1	0.9039 (11)	0.5243 (9)	0.1758 (9)	0.066 (3)
C2	0.7317 (12)	0.4506 (10)	0.1500 (9)	0.069 (3)
C3	0.6467 (11)	0.5303 (11)	0.1758 (10)	0.076 (3)
C4	0.7298 (11)	0.6737 (11)	0.2244 (10)	0.074 (3)
C5	0.8990 (11)	0.7414 (9)	0.2443 (8)	0.060 (3)
C6	0.6455 (15)	0.2922 (11)	0.1035 (13)	0.093 (4)
C7	1.0005 (10)	0.8939 (9)	0.2956 (8)	0.056 (3)
C8	0.9407 (12)	0.9933 (11)	0.3240 (10)	0.069 (3)
C9	1.0501 (13)	1.1320 (11)	0.3714 (11)	0.076 (3)
C10	1.2194 (13)	1.1753 (9)	0.3894 (10)	0.070 (3)
C11	1.2737 (11)	1.0742 (9)	0.3607 (8)	0.060 (3)
C12	1.3426 (14)	1.3307 (10)	0.4439 (12)	0.082 (4)
Au2	0.00000	0.00000	0.00000	0.0681 (2)
Cl3	0.2497 (5)	−0.0056 (5)	0.0129 (5)	0.1187 (16)
Cl4	0.1272 (6)	0.2391 (3)	0.0717 (3)	0.1093 (12)
Au3	1.00000	0.50000	0.50000	0.0654 (2)
Cl5	1.2288 (4)	0.7061 (3)	0.5439 (3)	0.0836 (7)*
H1	0.96620	0.47370	0.16190	0.0790*
H3	0.53150	0.48610	0.16010	0.0910*
H4	0.67160	0.72540	0.24380	0.0880*
H6A	0.62170	0.24230	0.17190	0.1400*
H6B	0.71750	0.25990	0.07430	0.1400*
H6C	0.54210	0.27280	0.03460	0.1400*
H8	0.82660	0.96600	0.31100	0.0820*
H9	1.00990	1.19880	0.39200	0.0910*
H11	1.38780	1.10100	0.37400	0.0730*
H12A	1.38440	1.34120	0.53520	0.1240*
H12B	1.28570	1.39460	0.41790	0.1240*
H12C	1.43510	1.35400	0.41270	0.1240*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Au1	0.0476 (2)	0.0555 (2)	0.0651 (2)	0.0246 (1)	0.0206 (1)	0.0069 (1)
Cl1	0.0748 (14)	0.0681 (12)	0.1089 (19)	0.0387 (10)	0.0390 (13)	0.0006 (12)
Cl2	0.0476 (10)	0.0728 (13)	0.113 (2)	0.0220 (9)	0.0284 (11)	0.0031 (13)
N1	0.053 (3)	0.062 (4)	0.059 (4)	0.019 (3)	0.017 (3)	0.002 (3)
N2	0.051 (3)	0.060 (3)	0.053 (4)	0.025 (3)	0.021 (3)	0.009 (3)
C1	0.062 (5)	0.057 (4)	0.074 (6)	0.015 (4)	0.027 (4)	0.002 (4)
C2	0.067 (5)	0.066 (5)	0.062 (5)	0.015 (4)	0.022 (4)	0.000 (4)
C3	0.051 (5)	0.080 (6)	0.079 (6)	0.007 (4)	0.023 (4)	0.003 (5)
C4	0.043 (4)	0.072 (5)	0.091 (7)	0.007 (4)	0.021 (4)	0.005 (5)
C5	0.057 (4)	0.066 (5)	0.061 (5)	0.025 (4)	0.025 (4)	0.011 (4)
C6	0.077 (7)	0.072 (6)	0.107 (9)	0.005 (5)	0.031 (6)	−0.010 (6)
C7	0.050 (4)	0.062 (4)	0.060 (5)	0.028 (3)	0.018 (3)	0.006 (4)
C8	0.061 (5)	0.078 (5)	0.079 (6)	0.036 (4)	0.030 (4)	0.012 (5)
C9	0.085 (6)	0.071 (5)	0.094 (7)	0.047 (5)	0.040 (5)	0.009 (5)
C10	0.084 (6)	0.054 (4)	0.071 (6)	0.027 (4)	0.026 (5)	0.011 (4)
C11	0.060 (5)	0.060 (4)	0.062 (5)	0.031 (4)	0.014 (4)	0.006 (4)
C12	0.087 (7)	0.057 (5)	0.103 (8)	0.031 (4)	0.029 (6)	0.007 (5)
Au2	0.0810 (3)	0.0527 (3)	0.0547 (3)	0.0170 (2)	0.0130 (2)	0.0067 (2)
Cl3	0.098 (2)	0.133 (3)	0.127 (3)	0.052 (2)	0.033 (2)	0.018 (2)
Cl4	0.160 (3)	0.0549 (12)	0.0797 (18)	0.0144 (15)	0.0305 (19)	0.0013 (11)
Au3	0.0724 (3)	0.0670 (3)	0.0672 (3)	0.0335 (2)	0.0296 (2)	0.0161 (2)

Geometric parameters (Å, º) top

Au1—N1	2.028 (9)	C5—C7	1.466 (12)
Au1—N2	2.027 (7)	C7—C8	1.375 (15)
Au1—Cl1	2.252 (3)	C8—C9	1.362 (15)
Au1—Cl2	2.262 (3)	C9—C10	1.380 (18)
Au2—Cl4ⁱ	2.261 (3)	C10—C11	1.355 (15)
Au2—Cl3ⁱ	2.246 (5)	C10—C12	1.530 (14)
Au2—Cl3	2.246 (5)	C1—H1	0.9300
Au2—Cl4	2.261 (3)	C3—H3	0.9300
Au3—Cl5ⁱⁱ	2.248 (3)	C4—H4	0.9300
Au3—Cl5	2.248 (3)	C6—H6B	0.9600
N1—C1	1.343 (12)	C6—H6A	0.9600
N1—C5	1.334 (13)	C6—H6C	0.9600
N2—C7	1.375 (13)	C8—H8	0.9300
N2—C11	1.339 (11)	C9—H9	0.9300
C1—C2	1.393 (15)	C11—H11	0.9300
C2—C3	1.380 (16)	C12—H12C	0.9600
C2—C6	1.496 (14)	C12—H12A	0.9600
C3—C4	1.369 (15)	C12—H12B	0.9600
C4—C5	1.375 (15)

Au1···Cl3ⁱⁱⁱ	3.588 (5)	N1···C7	2.368 (12)
Au1···Cl5	3.243 (3)	N1···Cl1	3.173 (9)
Au2···C7^iv	3.490 (8)	N2···Cl2	3.165 (9)
Au2···C7^v	3.490 (8)	N2···N1	2.619 (10)
Au3···C1	3.486 (9)	N2···C5	2.396 (12)
Au3···C1ⁱⁱ	3.486 (9)	C1···Au3	3.486 (9)
Cl1···Cl4^vi	3.394 (4)	C1···Au3	3.486 (9)
Cl1···N1	3.173 (9)	C3···Cl1^viii	3.625 (12)
Cl1···C1	3.203 (11)	C5···Cl4^iv	3.477 (9)
Cl1···Cl2	3.166 (4)	C6···Cl3	3.564 (14)
Cl1···C3^vi	3.625 (12)	C7···Au2^iv	3.490 (8)
Cl2···N2	3.165 (9)	C7···Au2ⁱⁱⁱ	3.490 (8)
Cl2···C11	3.233 (11)	C8···Cl3^iv	3.644 (12)
Cl2···Cl1	3.166 (4)	C10···Cl4ⁱⁱⁱ	3.513 (11)
Cl2···C11^vii	3.476 (9)	C11···Cl2^vii	3.476 (9)
Cl2···Cl5^vii	3.650 (4)	C12···C12^xi	3.448 (15)
Cl3···C6	3.564 (14)	C4···H8	2.8100
Cl3···C8^iv	3.644 (12)	C8···H4	2.7900
Cl3···Cl4	3.185 (7)	H1···Cl1	2.5900
Cl3···Au1^v	3.588 (5)	H1···H6B	2.3900
Cl3···Cl4ⁱ	3.188 (7)	H3···Cl1^viii	2.9300
Cl4···Cl3ⁱ	3.188 (7)	H3···H6C	2.5900
Cl4···C10^v	3.513 (11)	H4···C8	2.7900
Cl4···C5^iv	3.477 (9)	H4···Cl1^viii	3.1200
Cl4···Cl3	3.185 (7)	H4···Cl2^viii	3.0500
Cl4···Cl1^viii	3.394 (4)	H4···H8	2.2800
Cl4···N1^iv	3.367 (8)	H6A···Cl5ⁱⁱ	2.9900
Cl5···Au1	3.243 (3)	H6B···H1	2.3900
Cl5···Cl2^vii	3.650 (4)	H6B···Cl3^ix	2.8700
Cl1···H4^vi	3.1200	H6C···H3	2.5900
Cl1···H1	2.5900	H6C···Cl3	3.0200
Cl1···H3^vi	2.9300	H8···H4	2.2800
Cl2···H8^vi	2.7500	H8···C4	2.8100
Cl2···H11	2.6400	H8···Cl2^viii	2.7500
Cl2···H4^vi	3.0500	H9···H12B	2.4800
Cl3···H6C	3.0200	H9···Cl5^x	2.9300
Cl3···H6B^ix	2.8700	H11···Cl2	2.6400
Cl5···H11^vii	3.1200	H11···H12C	2.4300
Cl5···H6Aⁱⁱ	2.9900	H11···Cl5^vii	3.1200
Cl5···H9^x	2.9300	H12B···H9	2.4800
N1···Cl4^iv	3.367 (8)	H12C···H11	2.4300
N1···N2	2.619 (10)

Cl1—Au1—Cl2	89.07 (11)	C7—C8—C9	119.4 (11)
Cl1—Au1—N1	95.5 (2)	C8—C9—C10	121.3 (11)
Cl1—Au1—N2	175.8 (2)	C11—C10—C12	121.1 (11)
Cl2—Au1—N1	175.3 (2)	C9—C10—C11	117.6 (9)
Cl2—Au1—N2	95.0 (2)	C9—C10—C12	121.3 (10)
N1—Au1—N2	80.5 (3)	N2—C11—C10	122.5 (10)
Cl3ⁱ—Au2—Cl4ⁱ	89.95 (19)	C2—C1—H1	119.00
Cl3—Au2—Cl4ⁱ	90.05 (19)	N1—C1—H1	119.00
Cl3—Au2—Cl4	89.95 (19)	C2—C3—H3	120.00
Cl3—Au2—Cl3ⁱ	180.00	C4—C3—H3	120.00
Cl3ⁱ—Au2—Cl4	90.05 (19)	C3—C4—H4	120.00
Cl4—Au2—Cl4ⁱ	180.00	C5—C4—H4	120.00
Cl5—Au3—Cl5ⁱⁱ	180.00	C2—C6—H6A	109.00
Au1—N1—C1	124.0 (7)	C2—C6—H6B	109.00
Au1—N1—C5	115.3 (6)	C2—C6—H6C	109.00
C1—N1—C5	120.7 (9)	H6B—C6—H6C	109.00
Au1—N2—C11	126.2 (7)	H6A—C6—H6B	109.00
Au1—N2—C7	113.9 (5)	H6A—C6—H6C	109.00
C7—N2—C11	120.0 (8)	C7—C8—H8	120.00
N1—C1—C2	122.3 (10)	C9—C8—H8	120.00
C3—C2—C6	121.8 (11)	C10—C9—H9	119.00
C1—C2—C3	116.3 (9)	C8—C9—H9	119.00
C1—C2—C6	121.8 (10)	N2—C11—H11	119.00
C2—C3—C4	120.9 (10)	C10—C11—H11	119.00
C3—C4—C5	120.1 (10)	C10—C12—H12A	110.00
N1—C5—C4	119.7 (8)	C10—C12—H12B	109.00
N1—C5—C7	115.4 (9)	C10—C12—H12C	109.00
C4—C5—C7	124.8 (9)	H12A—C12—H12B	109.00
N2—C7—C5	115.0 (8)	H12A—C12—H12C	109.00
N2—C7—C8	119.3 (8)	H12B—C12—H12C	109.00
C5—C7—C8	125.8 (9)

Cl1—Au1—N1—C1	3.4 (7)	C11—N2—C7—C8	0.9 (12)
N2—Au1—N1—C1	−177.7 (8)	N1—C1—C2—C3	−1.7 (14)
Cl1—Au1—N1—C5	−179.5 (6)	N1—C1—C2—C6	−178.6 (10)
N2—Au1—N1—C5	−0.7 (6)	C6—C2—C3—C4	176.7 (10)
Cl2—Au1—N2—C7	−179.0 (5)	C1—C2—C3—C4	−0.2 (15)
N1—Au1—N2—C7	0.0 (6)	C2—C3—C4—C5	2.1 (16)
Cl2—Au1—N2—C11	1.5 (7)	C3—C4—C5—C7	180.0 (9)
N1—Au1—N2—C11	−179.5 (7)	C3—C4—C5—N1	−2.2 (14)
Au1—N1—C1—C2	178.6 (7)	C4—C5—C7—N2	176.7 (8)
C5—N1—C1—C2	1.7 (14)	C4—C5—C7—C8	−4.2 (15)
Au1—N1—C5—C4	−176.8 (7)	N1—C5—C7—N2	−1.2 (11)
C1—N1—C5—C4	0.4 (13)	N1—C5—C7—C8	177.9 (9)
Au1—N1—C5—C7	1.2 (10)	C5—C7—C8—C9	180.0 (9)
C1—N1—C5—C7	178.4 (8)	N2—C7—C8—C9	−0.9 (14)
Au1—N2—C11—C10	178.3 (7)	C7—C8—C9—C10	1.1 (16)
C7—N2—C11—C10	−1.1 (13)	C8—C9—C10—C11	−1.3 (16)
Au1—N2—C7—C8	−178.6 (7)	C8—C9—C10—C12	−179.4 (10)
Au1—N2—C7—C5	0.6 (9)	C12—C10—C11—N2	179.4 (9)
C11—N2—C7—C5	−179.9 (7)	C9—C10—C11—N2	1.3 (14)

Symmetry codes: (i) −x, −y, −z; (ii) −x+2, −y+1, −z+1; (iii) x+1, y+1, z; (iv) −x+1, −y+1, −z; (v) x−1, y−1, z; (vi) x+1, y, z; (vii) −x+3, −y+2, −z+1; (viii) x−1, y, z; (ix) −x+1, −y, −z; (x) −x+2, −y+2, −z+1; (xi) −x+3, −y+3, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···Cl1	0.93	2.59	3.203 (11)	124
C8—H8···Cl2^viii	0.93	2.75	3.666 (12)	169
C11—H11···Cl2	0.93	2.64	3.233 (11)	122

Symmetry code: (viii) x−1, y, z.

Experimental details

Crystal data
Chemical formula	[AuCl₂(C₁₂H₁₂N₂)]₂[AuCl₄][AuCl₂]
M_r	1510.86
Crystal system, space group	Triclinic, P1
Temperature (K)	295
a, b, c (Å)	9.0698 (4), 10.0886 (4), 11.1678 (5)
α, β, γ (°)	91.155 (4), 108.148 (4), 111.344 (3)
V (Å³)	894.09 (7)
Z	1
Radiation type	Mo Kα
µ (mm⁻¹)	17.13
Crystal size (mm)	0.41 × 0.28 × 0.08

Data collection
Diffractometer	Stoe IPDS2 diffractometer
Absorption correction	Integration (X-RED32; Stoe & Cie, 2002)
T_min, T_max	0.054, 0.341
No. of measured, independent and observed [I > 2σ(I)] reflections	9898, 3651, 3193
R_int	0.059
(sin θ/λ)_max (Å⁻¹)	0.628

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.112, 1.05
No. of reflections	3651
No. of parameters	191
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.64, −1.91

Computer programs: X-AREA (Stoe & Cie, 2002), X-RED32 (Stoe & Cie, 2002), SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).

Selected bond lengths (Å) top

Au1—N1	2.028 (9)	Au2—Cl3	2.246 (5)
Au1—N2	2.027 (7)	Au2—Cl4	2.261 (3)
Au1—Cl1	2.252 (3)	Au3—Cl5	2.248 (3)
Au1—Cl2	2.262 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···Cl1	0.93	2.59	3.203 (11)	124
C8—H8···Cl2ⁱ	0.93	2.75	3.666 (12)	169
C11—H11···Cl2	0.93	2.64	3.233 (11)	122

Symmetry code: (i) x−1, y, z.

Acknowledgements

The authors acknowledge the Faculty of Arts and Sciences, Ondokuz Mayıs University, Turkey, for the use of the Stoe IPDS-2 diffractometer (purchased under grant F.279 of the University Research Fund). NS, VA and AA are grateful to Shahid Beheshti University for financial support.

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