3-Phenyl­pyridinium tetra­chlorido­aurate(III)

Amani, V.; Safari, N.; Khavasi, H.R.

doi:10.1107/S1600536810006860

metal-organic compounds

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ISSN: 2056-9890

Volume 66| Part 3| March 2010| Page m345

doi:10.1107/S1600536810006860

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3-Phenylpyridinium tetrachloridoaurate(III)

Vahid Amani,^a Nasser Safari ^a ^* and Hamid Reza Khavasi ^a

^aDepartment of Chemistry, Shahid Beheshti University, G. C., Evin, Tehran 1983963113, Iran
^*Correspondence e-mail: n-safari@cc.sbu.ac.ir

(Received 21 February 2010; accepted 23 February 2010; online 27 February 2010)

In the title molecular salt, (C₁₁H₁₀N)[AuCl₄], the Au^III atom adopts an almost regular square-planar coordination geometry and the dihedral angle between the aromatic rings of the 3-phenylpyridinium cation is 23.1 (3)°. In the crystal, the ions interact 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_r = 494.97
Triclinic, $[P \overline 1]$
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[F² > 2σ(F²)] = 0.030
wR(F²) = 0.083
S = 1.15
3688 reflections
154 parameters
H-atom parameters constrained
Δρ_max = 1.19 e Å⁻³
Δρ_min = −1.85 e Å⁻³

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) -x+1, -y, -z+1.

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 ).

Supporting information

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

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

checkCIF report

Comment top

There are several proton transfer systems using HAuCl₄ with proton acceptor molecules, such as [EMI][AuCl₄], (II) and [BMI]₂[AuCl₄].2H₂O, (III), (Hasan et al., 1999), [H₂bipy][AuCl₄][Cl], (IV), (Zhang et al., 2006), [H₇O₃][15-crown-5][AuCl₄], (V) and [H₅O₂][benzo-15-crown-5]₂[AuCl₄], (VI), (Johnson & Steed, 1998), [H₅O₂]₂[12-crown-4]₂[AuCl₄]₂, (VII), [H₃O][18-crown-6][AuCl₄], (VIII) and [H₃O][4-nitrobenzo-18-crown-6][AuCl₄], (IX), (Calleja et al., 2001), [DPpy.H][AuCl₄], (X), (Yap et al., 1995),[H₂DA18C6][AuCl₄].2H2O, (XI), (Hojjat Kashani et al., 2008), [dafonium][dafone][AuCl₄], (XII), (Safari et al., 2009), [pz(py)₂.H][AuCl₄], (XIII), (Yıldırım, Akkurt, Safari, Amani & McKee 2009), [Ph₂Phen.H][AuCl₄], (XIV), (Yıldırım, Akkurt, Safari, Abedi et al., 2009) and [TBA]₂[AuCl₄][Cl], (XV), (Fazaeli et al., 2010) [Where EMI is 1-ethyl-3-methylimidazolium, BMI is 1-butyl-3-methylimidazolium, H₂bipy is 2,2'-bipyridinium, DPpy.H is 2,6-diphenylpyridinium, H₂DA18C6 is 1,10-diazonia-18-crown-6, dafonium is 9-oxo-4,5-diazafluoren-4-ium, dafone is 4,5-diazafluoren-9-one, pz(py)₂.H is 2-(3-pyridin-2-ylpyrazin-2-yl)pyridinium, Ph₂Phen.H is 2,9-dimethyl-4,7-diphenyl-1,10-phenanthrolin-1-ium and TBA is tribenzylammonium] 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).

The molecule of the title compound, (I), (Fig. 1), contains one independent protonated 3-phenylpyridinium cation and one [AuCl₄]^- anion. The Au^III atom has a squareplanar environment defined by four Cl atoms. In [AuCl₄]^- anion, the Au—Cl bond lengths and angles (Table 1) are within normal range (II, III, VII, VIII and IX).

In the crystal structure, intermolecular N—H···Cl and C—H···Cl hydrogen bonds (Table 2) link the molecules (Fig. 2), in which they may be effective in the stabilization of the structure.

Related literature top

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 top

A solution of 3-phenylpyridine (0.11 g, 0.09 ml, 0.74 mmol) in methanol (5 ml) was added to a solution of HAuCl₄.3H₂O, (0.29 g, 0.74 mmol) in acetonitrile (15 ml) and the resulting yellow solution was stirred for 30 min at 313 K. Then, it was left to evaporate slowly at room temperature. After five days, yellow blocks of (I) were isolated (yield 0.26 g; 71.0%).

Computing details top

Data collection: X-AREA (Stoe & Cie, 2005); cell refinement: X-AREA (Stoe & Cie, 2005); data reduction: X-AREA (Stoe & Cie, 2005); 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).

Figures top

	Fig. 1. The molecular structure of (I). Displacement ellipsoids are drawn at the 40% probability level.
	Fig. 2. Unit-cell packing diagram for (I). Hydrogen bonds are shown as dashed lines.

3-Phenylpyridinium tetrachloridoaurate(III) top

Crystal data top

(C₁₁H₁₀N)[AuCl₄]	Z = 2
M_r = 494.97	F(000) = 460
Triclinic, P1	D_x = 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

Data collection top

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

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)] = 0.030	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.083	H-atom parameters constrained
S = 1.15	w = 1/[σ²(F_o²) + (0.049P)² + 0.4225P] where P = (F_o² + 2F_c²)/3
3688 reflections	(Δ/σ)_max = 0.001
154 parameters	Δρ_max = 1.19 e Å⁻³
0 restraints	Δρ_min = −1.85 e Å⁻³

Crystal data top

(C₁₁H₁₀N)[AuCl₄]	γ = 97.216 (10)°
M_r = 494.97	V = 694.20 (15) Å³
Triclinic, P1	Z = 2
a = 7.7629 (9) Å	Mo Kα radiation
b = 8.5901 (11) Å	µ = 11.34 mm⁻¹
c = 11.0530 (15) Å	T = 298 K
α = 94.106 (11)°	0.40 × 0.35 × 0.28 mm
β = 107.125 (10)°

Data collection top

Stoe IPDS II diffractometer	3688 independent reflections
Absorption correction: numerical (X-RED; Stoe & Cie, 2005)	3513 reflections with I > 2σ(I)
T_min = 0.067, T_max = 0.180	R_int = 0.051
7980 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.030	0 restraints
wR(F²) = 0.083	H-atom parameters constrained
S = 1.15	Δρ_max = 1.19 e Å⁻³
3688 reflections	Δρ_min = −1.85 e Å⁻³
154 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) −x+1, −y, −z+1.

Experimental details

Crystal data
Chemical formula	(C₁₁H₁₀N)[AuCl₄]
M_r	494.97
Crystal system, space group	Triclinic, P1
Temperature (K)	298
a, b, c (Å)	7.7629 (9), 8.5901 (11), 11.0530 (15)
α, β, γ (°)	94.106 (11), 107.125 (10), 97.216 (10)
V (Å³)	694.20 (15)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	11.34
Crystal size (mm)	0.40 × 0.35 × 0.28

Data collection
Diffractometer	Stoe IPDS II diffractometer
Absorption correction	Numerical (X-RED; Stoe & Cie, 2005)
T_min, T_max	0.067, 0.180
No. of measured, independent and observed [I > 2σ(I)] reflections	7980, 3688, 3513
R_int	0.051
(sin θ/λ)_max (Å⁻¹)	0.686

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.030, 0.083, 1.15
No. of reflections	3688
No. of parameters	154
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.19, −1.85

Computer programs: X-AREA (Stoe & Cie, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), WinGX (Farrugia, 1999).

Selected bond lengths (Å) top

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

Hydrogen-bond geometry (Å, º) top

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) −x+1, −y, −z+1.

Acknowledgements

We thank the Graduate Study Councils of Shahid Beheshti University for financial support (Project 600/1555).

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