6,6'-Dimethyl-2,2'-bipyridin-1-ium tetra-chloridoaurate(III).

In the anion of the title compound, (C(12)H(13)N(2))[AuCl(4)], the Au(III) atom has a square-planar coordination. In the crystal, inter-molecular N-H⋯Cl and C-H⋯Cl hydrogen bonds and π-π contacts between the pyridine rings [centroid-centroid distance = 3.5419 (19) Å] result in the formation of a supra-molecular structure.

Related literature

For related structures, see: Abedi et al. (2008 ▶, 2011 ▶); Amani et al. (2010 ▶); Calleja et al. (2001 ▶); Faza­eli et al. (2010 ▶); Hasan et al. (1999 ▶); Hojjat Kashani et al. (2008 ▶); Johnson & Steed (1998 ▶); Kalateh et al. (2008 ▶); Safari et al. (2009 ▶); Yap et al. (1995 ▶); Yıldırım et al. (2009a ▶,b ▶); Zhang et al. (2006 ▶).

Experimental

Crystal data

(C12H13N2)[AuCl4]

M = 524.01

Monoclinic,

a = 10.8942 (9) Å

b = 11.6784 (10) Å

c = 12.2866 (11) Å

β = 95.772 (5)°

V = 1555.3 (2) Å3

Z = 4

Mo Kα radiation

μ = 10.13 mm−1

T = 100 K

0.20 × 0.15 × 0.15 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.182, T max = 0.227

12293 measured reflections

4101 independent reflections

3699 reflections with I > 2σ(I)

R int = 0.032

Refinement

R[F 2 > 2σ(F 2)] = 0.023

wR(F 2) = 0.049

S = 1.00

4101 reflections

174 parameters

H-atom parameters constrained

Δρmax = 0.83 e Å−3

Δρmin = −1.15 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: XP in SHELXTL (Sheldrick, 2008 ▶) and Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S160053681202853X/hy2560sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681202853X/hy2560Isup2.hkl

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

(C12H13N2)[AuCl4]	F(000) = 984
Mr = 524.01	Dx = 2.238 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1542 reflections
a = 10.8942 (9) Å	θ = 3.0–30.0°
b = 11.6784 (10) Å	µ = 10.13 mm−1
c = 12.2866 (11) Å	T = 100 K
β = 95.772 (5)°	Prism, yellow
V = 1555.3 (2) Å3	0.20 × 0.15 × 0.15 mm
Z = 4

Bruker APEXII CCD diffractometer	4101 independent reflections
Radiation source: fine-focus sealed tube	3699 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.032
φ and ω scans	θmax = 29.0°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −14→14
Tmin = 0.182, Tmax = 0.227	k = −15→15
12293 measured reflections	l = −16→16

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)] = 0.023	Hydrogen site location: mixed
wR(F2) = 0.049	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.0228P)2 + 0.3281P] where P = (Fo2 + 2Fc2)/3
4101 reflections	(Δ/σ)max = 0.002
174 parameters	Δρmax = 0.83 e Å−3
0 restraints	Δρmin = −1.15 e Å−3

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.

	x	y	z	Uiso*/Ueq
Au1	0.910926 (11)	0.846230 (10)	0.536181 (9)	0.00895 (4)
Cl1	1.05716 (8)	0.80777 (8)	0.67847 (7)	0.01993 (18)
Cl2	0.76133 (7)	0.82538 (7)	0.65184 (6)	0.01523 (16)
Cl3	0.76425 (7)	0.88766 (7)	0.39541 (6)	0.01501 (16)
Cl4	1.05950 (7)	0.86081 (7)	0.41815 (7)	0.01552 (16)
N1	0.7935 (2)	0.0942 (2)	0.0534 (2)	0.0096 (5)
N2	0.9773 (2)	0.2313 (2)	0.0264 (2)	0.0102 (5)
H2N	0.9224	0.2323	0.0676	0.012*
C1	0.8500 (3)	0.0735 (3)	−0.0370 (2)	0.0089 (6)
C2	0.6953 (3)	0.0310 (3)	0.0722 (2)	0.0107 (6)
C3	0.6523 (3)	−0.0561 (3)	0.0007 (3)	0.0136 (6)
H3A	0.5832	−0.1010	0.0158	0.016*
C4	0.7107 (3)	−0.0771 (3)	−0.0928 (3)	0.0154 (7)
H4A	0.6818	−0.1361	−0.1422	0.018*
C5	0.8112 (3)	−0.0112 (3)	−0.1130 (3)	0.0131 (6)
H5A	0.8526	−0.0231	−0.1766	0.016*
C6	0.6349 (3)	0.0588 (3)	0.1736 (3)	0.0146 (7)
H6A	0.6978	0.0635	0.2363	0.022*
H6B	0.5754	−0.0013	0.1867	0.022*
H6C	0.5920	0.1325	0.1640	0.022*
C7	0.9564 (3)	0.1483 (3)	−0.0502 (3)	0.0098 (6)
C8	1.0677 (3)	0.3099 (3)	0.0276 (3)	0.0129 (6)
C9	1.1446 (3)	0.3059 (3)	−0.0547 (3)	0.0144 (7)
H9A	1.2088	0.3605	−0.0571	0.017*
C10	1.1274 (3)	0.2212 (3)	−0.1343 (3)	0.0148 (7)
H10A	1.1808	0.2183	−0.1908	0.018*
C11	1.0340 (3)	0.1407 (3)	−0.1328 (3)	0.0124 (6)
H11A	1.0234	0.0822	−0.1867	0.015*
C12	1.0788 (3)	0.3951 (3)	0.1189 (3)	0.0185 (7)
H12A	1.1431	0.4510	0.1067	0.028*
H12B	1.1007	0.3555	0.1885	0.028*
H12C	0.9999	0.4348	0.1215	0.028*

	U11	U22	U33	U12	U13	U23
Au1	0.00970 (6)	0.00822 (7)	0.00884 (6)	0.00079 (4)	0.00044 (4)	−0.00109 (4)
Cl1	0.0138 (4)	0.0335 (5)	0.0120 (4)	0.0015 (4)	−0.0011 (3)	0.0048 (3)
Cl2	0.0142 (4)	0.0191 (4)	0.0129 (3)	−0.0038 (3)	0.0041 (3)	−0.0045 (3)
Cl3	0.0141 (4)	0.0159 (4)	0.0143 (3)	0.0012 (3)	−0.0021 (3)	0.0022 (3)
Cl4	0.0134 (4)	0.0201 (4)	0.0136 (4)	0.0027 (3)	0.0039 (3)	0.0017 (3)
N1	0.0119 (13)	0.0076 (13)	0.0093 (12)	0.0009 (10)	0.0004 (10)	0.0012 (10)
N2	0.0088 (12)	0.0109 (13)	0.0113 (12)	−0.0010 (10)	0.0022 (10)	−0.0012 (10)
C1	0.0084 (14)	0.0084 (14)	0.0098 (13)	0.0040 (11)	0.0010 (11)	0.0008 (11)
C2	0.0134 (15)	0.0090 (15)	0.0096 (13)	0.0033 (12)	0.0002 (11)	0.0027 (12)
C3	0.0116 (15)	0.0122 (16)	0.0167 (15)	−0.0024 (13)	−0.0002 (12)	0.0004 (13)
C4	0.0167 (16)	0.0137 (16)	0.0153 (15)	−0.0034 (13)	−0.0009 (13)	−0.0062 (13)
C5	0.0175 (16)	0.0119 (16)	0.0099 (14)	0.0000 (13)	0.0022 (12)	−0.0024 (12)
C6	0.0161 (16)	0.0156 (17)	0.0125 (15)	−0.0028 (13)	0.0036 (12)	0.0015 (13)
C7	0.0099 (14)	0.0092 (15)	0.0099 (14)	0.0004 (12)	−0.0013 (11)	0.0001 (12)
C8	0.0138 (15)	0.0088 (15)	0.0157 (15)	−0.0023 (13)	−0.0009 (12)	0.0009 (12)
C9	0.0104 (15)	0.0160 (17)	0.0167 (16)	−0.0015 (13)	0.0004 (13)	0.0040 (13)
C10	0.0125 (15)	0.0185 (17)	0.0137 (15)	0.0027 (13)	0.0027 (12)	0.0033 (13)
C11	0.0143 (15)	0.0129 (16)	0.0098 (14)	0.0010 (13)	−0.0006 (12)	−0.0008 (12)
C12	0.0186 (17)	0.0157 (17)	0.0215 (17)	−0.0050 (14)	0.0032 (14)	−0.0072 (14)

Au1—Cl2	2.2804 (8)	C4—H4A	0.9500
Au1—Cl3	2.2854 (8)	C5—H5A	0.9500
Au1—Cl4	2.2856 (8)	C6—H6A	0.9800
Au1—Cl1	2.2882 (8)	C6—H6B	0.9800
N1—C2	1.339 (4)	C6—H6C	0.9800
N1—C1	1.345 (4)	C7—C11	1.388 (5)
N2—C8	1.345 (4)	C8—C9	1.378 (5)
N2—C7	1.353 (4)	C8—C12	1.496 (5)
N2—H2N	0.8221	C9—C10	1.390 (5)
C1—C5	1.396 (4)	C9—H9A	0.9500
C1—C7	1.474 (4)	C10—C11	1.387 (5)
C2—C3	1.395 (4)	C10—H10A	0.9500
C2—C6	1.502 (4)	C11—H11A	0.9500
C3—C4	1.390 (5)	C12—H12A	0.9800
C3—H3A	0.9500	C12—H12B	0.9800
C4—C5	1.382 (5)	C12—H12C	0.9800
Cl2—Au1—Cl3	90.29 (3)	C2—C6—H6B	109.5
Cl2—Au1—Cl4	178.02 (3)	H6A—C6—H6B	109.5
Cl3—Au1—Cl4	89.42 (3)	C2—C6—H6C	109.5
Cl2—Au1—Cl1	89.38 (3)	H6A—C6—H6C	109.5
Cl3—Au1—Cl1	179.00 (3)	H6B—C6—H6C	109.5
Cl4—Au1—Cl1	90.94 (3)	N2—C7—C11	118.8 (3)
C2—N1—C1	118.9 (3)	N2—C7—C1	115.3 (3)
C8—N2—C7	124.6 (3)	C11—C7—C1	125.8 (3)
C8—N2—H2N	124.1	N2—C8—C9	117.8 (3)
C7—N2—H2N	110.9	N2—C8—C12	117.8 (3)
N1—C1—C5	123.1 (3)	C9—C8—C12	124.3 (3)
N1—C1—C7	114.5 (3)	C8—C9—C10	119.5 (3)
C5—C1—C7	122.4 (3)	C8—C9—H9A	120.3
N1—C2—C3	121.1 (3)	C10—C9—H9A	120.3
N1—C2—C6	116.6 (3)	C11—C10—C9	121.3 (3)
C3—C2—C6	122.2 (3)	C11—C10—H10A	119.3
C4—C3—C2	119.8 (3)	C9—C10—H10A	119.3
C4—C3—H3A	120.1	C10—C11—C7	117.9 (3)
C2—C3—H3A	120.1	C10—C11—H11A	121.1
C5—C4—C3	119.2 (3)	C7—C11—H11A	121.1
C5—C4—H4A	120.4	C8—C12—H12A	109.5
C3—C4—H4A	120.4	C8—C12—H12B	109.5
C4—C5—C1	117.8 (3)	H12A—C12—H12B	109.5
C4—C5—H5A	121.1	C8—C12—H12C	109.5
C1—C5—H5A	121.1	H12A—C12—H12C	109.5
C2—C6—H6A	109.5	H12B—C12—H12C	109.5
C2—N1—C1—C5	0.0 (4)	N1—C1—C7—N2	−3.9 (4)
C2—N1—C1—C7	179.6 (3)	C5—C1—C7—N2	175.6 (3)
C1—N1—C2—C3	0.8 (4)	N1—C1—C7—C11	176.4 (3)
C1—N1—C2—C6	−179.2 (3)	C5—C1—C7—C11	−4.1 (5)
N1—C2—C3—C4	−1.0 (5)	C7—N2—C8—C9	0.0 (5)
C6—C2—C3—C4	179.1 (3)	C7—N2—C8—C12	−179.4 (3)
C2—C3—C4—C5	0.3 (5)	N2—C8—C9—C10	−0.8 (5)
C3—C4—C5—C1	0.6 (5)	C12—C8—C9—C10	178.6 (3)
N1—C1—C5—C4	−0.7 (5)	C8—C9—C10—C11	0.3 (5)
C7—C1—C5—C4	179.7 (3)	C9—C10—C11—C7	1.0 (5)
C8—N2—C7—C11	1.3 (5)	N2—C7—C11—C10	−1.8 (4)
C8—N2—C7—C1	−178.4 (3)	C1—C7—C11—C10	177.9 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2N···Cl3i	0.82	2.80	3.419 (2)	134
C4—H4A···Cl2ii	0.95	2.79	3.434 (4)	126

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2N⋯Cl3i	0.82	2.80	3.419 (2)	134
C4—H4A⋯Cl2ii	0.95	2.79	3.434 (4)	126

Symmetry codes: (i) ; (ii) .