3-Phenyl-pyridinium tetra-chlorido-aurate(III).

In the title mol-ecular salt, (C(11)H(10)N)[AuCl(4)], the Au(III) atom adopts an almost regular square-planar coordination geometry and the dihedral angle between the aromatic rings of the 3-phenyl-pyridinium cation is 23.1 (3)°. In the crystal, the ions inter-act by way of N-H⋯Cl and C-H⋯Cl hydrogen bonds.

Related literature

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

Experimental

Crystal data

(C11H10N)[AuCl4]

M = 494.97

Triclinic,

a = 7.7629 (9) Å

b = 8.5901 (11) Å

c = 11.0530 (15) Å

α = 94.106 (11)°

β = 107.125 (10)°

γ = 97.216 (10)°

V = 694.20 (15) Å3

Z = 2

Mo Kα radiation

μ = 11.34 mm−1

T = 298 K

0.40 × 0.35 × 0.28 mm

Data collection

Stoe IPDSII diffractometer

Absorption correction: numerical (X-RED; Stoe & Cie, 2005 ▶) T min = 0.067, T max = 0.180

7980 measured reflections

3688 independent reflections

3513 reflections with I > 2σ(I)

R int = 0.051

Refinement

R[F 2 > 2σ(F 2)] = 0.030

wR(F 2) = 0.083

S = 1.15

3688 reflections

154 parameters

H-atom parameters constrained

Δρmax = 1.19 e Å−3

Δρmin = −1.85 e Å−3

Data collection: X-AREA (Stoe & Cie, 2005 ▶); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); 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 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810006860/hb5341sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810006860/hb5341Isup2.hkl

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

(C11H10N)[AuCl4]	Z = 2
Mr = 494.97	F(000) = 460
Triclinic, P1	Dx = 2.368 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.7629 (9) Å	Cell parameters from 984 reflections
b = 8.5901 (11) Å	θ = 1.9–29.2°
c = 11.0530 (15) Å	µ = 11.34 mm−1
α = 94.106 (11)°	T = 298 K
β = 107.125 (10)°	Block, yellow
γ = 97.216 (10)°	0.40 × 0.35 × 0.28 mm
V = 694.20 (15) Å3

Stoe IPDS II diffractometer	3688 independent reflections
Radiation source: fine-focus sealed tube	3513 reflections with I > 2σ(I)
graphite	Rint = 0.051
Detector resolution: 0.15 mm pixels mm-1	θmax = 29.2°, θmin = 1.9°
rotation method scans	h = −10→10
Absorption correction: numerical (X-RED; Stoe & Cie, 2005)	k = −11→11
Tmin = 0.067, Tmax = 0.180	l = −15→15
7980 measured reflections

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)] = 0.030	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.083	H-atom parameters constrained
S = 1.15	w = 1/[σ2(Fo2) + (0.049P)2 + 0.4225P] where P = (Fo2 + 2Fc2)/3
3688 reflections	(Δ/σ)max = 0.001
154 parameters	Δρmax = 1.19 e Å−3
0 restraints	Δρmin = −1.85 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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
C1	0.3073 (8)	0.3645 (7)	0.7222 (6)	0.0534 (13)
H1	0.4141	0.3203	0.7415	0.064*
C2	−0.0102 (9)	0.3328 (8)	0.6148 (7)	0.0593 (14)
H2	−0.1157	0.2683	0.5638	0.071*
C3	−0.0149 (8)	0.4824 (7)	0.6606 (6)	0.0556 (13)
H3	−0.1242	0.5229	0.6395	0.067*
C4	0.1433 (8)	0.5748 (6)	0.7388 (6)	0.0487 (11)
H4	0.1386	0.6775	0.7691	0.058*
C5	0.3102 (7)	0.5176 (6)	0.7733 (5)	0.0412 (9)
C6	0.4797 (7)	0.6118 (6)	0.8579 (5)	0.0429 (9)
C7	0.4751 (9)	0.7355 (7)	0.9442 (6)	0.0556 (13)
H7	0.3628	0.7566	0.9497	0.067*
C8	0.6310 (11)	0.8273 (9)	1.0215 (7)	0.0693 (18)
H8	0.6239	0.9105	1.0776	0.083*
C9	0.7981 (10)	0.7962 (10)	1.0160 (7)	0.0676 (17)
H9	0.9042	0.8600	1.0669	0.081*
C10	0.8084 (9)	0.6706 (10)	0.9353 (8)	0.0721 (19)
H10	0.9217	0.6470	0.9342	0.087*
C11	0.6485 (8)	0.5781 (8)	0.8545 (6)	0.0591 (14)
H11	0.6556	0.4944	0.7989	0.071*
N1	0.1525 (9)	0.2805 (7)	0.6455 (6)	0.0651 (14)
H1A	0.1565	0.1871	0.6136	0.078*
Au1	0.377224 (19)	0.071414 (17)	0.338315 (15)	0.03590 (7)
Cl1	0.08562 (18)	0.08586 (18)	0.33626 (17)	0.0559 (3)
Cl2	0.4746 (2)	0.30376 (17)	0.46750 (16)	0.0571 (3)
Cl3	0.67028 (17)	0.05728 (17)	0.34422 (16)	0.0509 (3)
Cl4	0.28061 (19)	−0.15918 (17)	0.20634 (17)	0.0581 (3)

	U11	U22	U33	U12	U13	U23
C1	0.051 (3)	0.046 (3)	0.063 (3)	0.013 (2)	0.019 (2)	−0.006 (2)
C2	0.056 (3)	0.052 (3)	0.064 (3)	−0.004 (2)	0.016 (3)	−0.002 (3)
C3	0.046 (3)	0.052 (3)	0.067 (3)	0.008 (2)	0.016 (2)	0.004 (3)
C4	0.053 (3)	0.039 (2)	0.057 (3)	0.012 (2)	0.019 (2)	0.003 (2)
C5	0.047 (2)	0.037 (2)	0.045 (2)	0.0093 (18)	0.0195 (19)	0.0048 (17)
C6	0.046 (2)	0.042 (2)	0.044 (2)	0.0103 (18)	0.0162 (19)	0.0077 (18)
C7	0.057 (3)	0.054 (3)	0.053 (3)	0.013 (2)	0.014 (2)	−0.005 (2)
C8	0.072 (4)	0.066 (4)	0.057 (3)	0.009 (3)	0.004 (3)	−0.010 (3)
C9	0.053 (3)	0.078 (4)	0.064 (4)	0.005 (3)	0.007 (3)	0.011 (3)
C10	0.042 (3)	0.098 (5)	0.075 (4)	0.012 (3)	0.016 (3)	0.011 (4)
C11	0.050 (3)	0.066 (3)	0.064 (3)	0.012 (3)	0.023 (3)	−0.001 (3)
N1	0.071 (3)	0.045 (2)	0.074 (3)	0.011 (2)	0.018 (3)	−0.011 (2)
Au1	0.02898 (10)	0.03416 (10)	0.04446 (11)	0.00715 (6)	0.01061 (7)	0.00261 (7)
Cl1	0.0343 (5)	0.0527 (6)	0.0830 (9)	0.0122 (5)	0.0208 (6)	0.0012 (6)
Cl2	0.0560 (7)	0.0460 (6)	0.0653 (8)	0.0017 (5)	0.0195 (6)	−0.0122 (6)
Cl3	0.0307 (5)	0.0498 (6)	0.0711 (8)	0.0074 (4)	0.0153 (5)	−0.0007 (6)
Cl4	0.0428 (6)	0.0492 (6)	0.0737 (9)	0.0055 (5)	0.0108 (6)	−0.0164 (6)

C1—N1	1.333 (8)	C7—H7	0.9300
C1—C5	1.389 (7)	C8—C9	1.375 (12)
C1—H1	0.9300	C8—H8	0.9300
C2—N1	1.351 (9)	C9—C10	1.376 (11)
C2—C3	1.356 (9)	C9—H9	0.9300
C2—H2	0.9300	C10—C11	1.403 (9)
C3—C4	1.384 (8)	C10—H10	0.9300
C3—H3	0.9300	C11—H11	0.9300
C4—C5	1.400 (7)	N1—H1A	0.8600
C4—H4	0.9300	Au1—Cl2	2.2740 (13)
C5—C6	1.470 (8)	Au1—Cl3	2.2754 (12)
C6—C11	1.388 (8)	Au1—Cl1	2.2762 (12)
C6—C7	1.388 (7)	Au1—Cl4	2.2766 (13)
C7—C8	1.368 (9)
N1—C1—C5	120.5 (5)	C7—C8—C9	119.8 (7)
N1—C1—H1	119.7	C7—C8—H8	120.1
C5—C1—H1	119.7	C9—C8—H8	120.1
N1—C2—C3	117.9 (6)	C8—C9—C10	120.0 (7)
N1—C2—H2	121.0	C8—C9—H9	120.0
C3—C2—H2	121.0	C10—C9—H9	120.0
C2—C3—C4	119.9 (6)	C9—C10—C11	120.2 (6)
C2—C3—H3	120.0	C9—C10—H10	119.9
C4—C3—H3	120.0	C11—C10—H10	119.9
C3—C4—C5	121.7 (5)	C6—C11—C10	119.8 (6)
C3—C4—H4	119.2	C6—C11—H11	120.1
C5—C4—H4	119.2	C10—C11—H11	120.1
C1—C5—C4	115.8 (5)	C1—N1—C2	124.0 (5)
C1—C5—C6	121.2 (5)	C1—N1—H1A	118.0
C4—C5—C6	123.0 (4)	C2—N1—H1A	118.0
C11—C6—C7	118.3 (5)	Cl2—Au1—Cl3	89.51 (5)
C11—C6—C5	120.8 (5)	Cl2—Au1—Cl1	89.92 (6)
C7—C6—C5	120.8 (5)	Cl3—Au1—Cl1	178.98 (5)
C8—C7—C6	121.8 (6)	Cl2—Au1—Cl4	179.07 (6)
C8—C7—H7	119.1	Cl3—Au1—Cl4	90.20 (5)
C6—C7—H7	119.1	Cl1—Au1—Cl4	90.38 (5)
N1—C2—C3—C4	−1.5 (10)	C11—C6—C7—C8	2.5 (10)
C2—C3—C4—C5	−0.5 (10)	C5—C6—C7—C8	−178.3 (6)
N1—C1—C5—C4	−0.2 (9)	C6—C7—C8—C9	−1.0 (12)
N1—C1—C5—C6	−180.0 (6)	C7—C8—C9—C10	−1.6 (13)
C3—C4—C5—C1	1.3 (9)	C8—C9—C10—C11	2.7 (12)
C3—C4—C5—C6	−178.9 (5)	C7—C6—C11—C10	−1.4 (10)
C1—C5—C6—C11	23.1 (8)	C5—C6—C11—C10	179.4 (6)
C4—C5—C6—C11	−156.7 (6)	C9—C10—C11—C6	−1.1 (12)
C1—C5—C6—C7	−156.1 (6)	C5—C1—N1—C2	−1.9 (11)
C4—C5—C6—C7	24.1 (8)	C3—C2—N1—C1	2.8 (11)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···Cl3i	0.86	2.63	3.359 (7)	143
C1—H1···Cl4i	0.93	2.83	3.755 (7)	175

Table 1

Selected bond lengths (Å)

Au1—Cl2	2.2740 (13)
Au1—Cl3	2.2754 (12)
Au1—Cl1	2.2762 (12)
Au1—Cl4	2.2766 (13)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯Cl3i	0.86	2.63	3.359 (7)	143
C1—H1⋯Cl4i	0.93	2.83	3.755 (7)	175

Symmetry code: (i) .