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The AuIII atom in the title compound, [AuCl3(C11H9N)], exists in a square planar AuCl3N geometry. The phenyl ring of the ligand is twisted by 51.6 (3)° with respect to the pyridyl ring.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807021307/hb2395sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807021307/hb2395Isup2.hkl
Contains datablock I

CCDC reference: 650535

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.010 Å
  • R factor = 0.022
  • wR factor = 0.079
  • Data-to-parameter ratio = 20.4

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT150_ALERT_1_C Volume as Calculated Differs from that Given ... 649.20 Ang-3 PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ? PLAT153_ALERT_1_C The su's on the Cell Axes are Equal (x 100000) 200 Ang. PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for Au1 PLAT342_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ... 10
Alert level G PLAT794_ALERT_5_G Check Predicted Bond Valency for Au1 (3) 3.06
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 5 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 1 ALERT type 5 Informative message, check

Comment top

A previous study reported the crystal structure of 4,4'-bipyridinium tetrachloroaurate(III) chloride, which was obtained unexpectedly from the reaction of 4,4'-bipyridine and potassium tetrachloraurate (Zhang et al., 2006). The direct reaction of 2-phenylpyridine with gold chloride yielded the expected title compound (I), which has the metal center in a square plane that is composed of the donor nitrogen site along with three chlorine atoms (Table 1, Fig. 1).

Related literature top

For the synthesis of the compound, see: Constable & Leese, 1989. The compound is a precursor to (2-phenylpyridyl-κN,κC)gold(III) dichloride (Fan et al., 2003).

For related literature, see: Zhang et al. (2006).

Experimental top

This compound was prepared as described in the literature (Constable & Leese, 1989). Bright-yellow crystals of (I) were obtained by its recrystalization from aqueous acetonitrile (xx:xx v/v).

Refinement top

The H atoms were placed in calculated positions [C—H 0.93 Å; U(H) = 1.2Ueq(C)]. The highest peak in the final difference map is 0.9 Å from Au1 and the deepest hole is 0.7 Å from Au1.

Structure description top

A previous study reported the crystal structure of 4,4'-bipyridinium tetrachloroaurate(III) chloride, which was obtained unexpectedly from the reaction of 4,4'-bipyridine and potassium tetrachloraurate (Zhang et al., 2006). The direct reaction of 2-phenylpyridine with gold chloride yielded the expected title compound (I), which has the metal center in a square plane that is composed of the donor nitrogen site along with three chlorine atoms (Table 1, Fig. 1).

For the synthesis of the compound, see: Constable & Leese, 1989. The compound is a precursor to (2-phenylpyridyl-κN,κC)gold(III) dichloride (Fan et al., 2003).

For related literature, see: Zhang et al. (2006).

Computing details top

Data collection: RAPID-AUTO (Rigaku Corporation, 1998); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2007).

Figures top
[Figure 1] Fig. 1. View of the molecular structure of (I) with displacement ellipsoids drawn at the 50% probability level (arbitary spheres for the H atoms).
Trichlorido(2-phenylpyridine-κN)gold(III) top
Crystal data top
[AuCl3(C11H9N)]Z = 2
Mr = 458.51F(000) = 424
Triclinic, P1Dx = 2.346 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.192 (2) ÅCell parameters from 6137 reflections
b = 9.078 (2) Åθ = 3.0–27.5°
c = 10.296 (2) ŵ = 11.92 mm1
α = 66.28 (3)°T = 298 K
β = 83.74 (3)°Block, yellow
γ = 68.02 (2)°0.29 × 0.24 × 0.18 mm
V = 649.2 (2) Å3
Data collection top
Rigaku R-AXIS RAPID IP
diffractometer
2952 independent reflections
Radiation source: fine-focus sealed tube2823 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.022
ω scanθmax = 27.5°, θmin = 3.0°
Absorption correction: mumerical
(NUMABS; Higashi, 1995)
h = 1010
Tmin = 0.090, Tmax = 0.223k = 1111
6439 measured reflectionsl = 1313
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.022Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.079H-atom parameters constrained
S = 1.30 w = 1/[σ2(Fo2) + (0.0425P)2 + 0.2981P]
where P = (Fo2 + 2Fc2)/3
2952 reflections(Δ/σ)max = 0.001
145 parametersΔρmax = 1.06 e Å3
0 restraintsΔρmin = 0.92 e Å3
Crystal data top
[AuCl3(C11H9N)]γ = 68.02 (2)°
Mr = 458.51V = 649.2 (2) Å3
Triclinic, P1Z = 2
a = 8.192 (2) ÅMo Kα radiation
b = 9.078 (2) ŵ = 11.92 mm1
c = 10.296 (2) ÅT = 298 K
α = 66.28 (3)°0.29 × 0.24 × 0.18 mm
β = 83.74 (3)°
Data collection top
Rigaku R-AXIS RAPID IP
diffractometer
2952 independent reflections
Absorption correction: mumerical
(NUMABS; Higashi, 1995)
2823 reflections with I > 2σ(I)
Tmin = 0.090, Tmax = 0.223Rint = 0.022
6439 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0220 restraints
wR(F2) = 0.079H-atom parameters constrained
S = 1.30Δρmax = 1.06 e Å3
2952 reflectionsΔρmin = 0.92 e Å3
145 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Au10.60793 (2)0.81841 (2)0.703793 (18)0.03193 (9)
Cl10.4693 (2)0.8672 (3)0.8937 (2)0.0564 (4)
Cl20.7651 (2)0.9810 (2)0.6926 (2)0.0524 (4)
Cl30.7367 (2)0.7757 (2)0.50767 (17)0.0468 (3)
N10.4665 (6)0.6723 (6)0.7124 (5)0.0387 (10)
C10.2963 (7)0.7577 (8)0.6642 (7)0.0450 (12)
H10.24640.87590.64210.054*
C20.1949 (8)0.6762 (10)0.6468 (7)0.0528 (15)
H20.07720.73680.61510.063*
C30.2731 (10)0.4994 (11)0.6779 (8)0.0597 (18)
H30.20950.44040.66420.072*
C40.4429 (9)0.4153 (9)0.7283 (7)0.0519 (14)
H40.49490.29710.75120.062*
C50.5401 (8)0.5015 (7)0.7465 (6)0.0406 (11)
C60.7262 (7)0.4083 (7)0.8082 (6)0.0384 (11)
C70.7772 (8)0.4233 (7)0.9251 (6)0.0435 (12)
H70.69820.49970.96190.052*
C80.9457 (9)0.3244 (9)0.9872 (8)0.0527 (14)
H80.97910.33321.06640.063*
C91.0635 (9)0.2131 (9)0.9316 (8)0.0563 (16)
H91.17680.14690.97280.068*
C101.0126 (9)0.2001 (8)0.8141 (8)0.0532 (15)
H101.09240.12510.77650.064*
C110.8458 (8)0.2966 (7)0.7525 (7)0.0470 (13)
H110.81310.28700.67340.056*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Au10.03303 (12)0.02905 (12)0.03363 (13)0.00925 (8)0.00320 (8)0.01286 (8)
Cl10.0579 (9)0.0643 (10)0.0499 (9)0.0134 (8)0.0078 (7)0.0345 (8)
Cl20.0608 (9)0.0451 (7)0.0611 (10)0.0273 (7)0.0070 (7)0.0205 (7)
Cl30.0538 (8)0.0525 (8)0.0415 (8)0.0237 (7)0.0098 (6)0.0235 (6)
N10.042 (2)0.045 (2)0.037 (2)0.023 (2)0.0048 (19)0.018 (2)
C10.040 (3)0.054 (3)0.043 (3)0.018 (3)0.000 (2)0.020 (3)
C20.040 (3)0.076 (4)0.049 (4)0.029 (3)0.000 (3)0.024 (3)
C30.072 (4)0.077 (5)0.060 (4)0.053 (4)0.010 (3)0.034 (4)
C40.063 (4)0.047 (3)0.054 (4)0.030 (3)0.002 (3)0.018 (3)
C50.051 (3)0.044 (3)0.032 (3)0.023 (2)0.001 (2)0.014 (2)
C60.048 (3)0.034 (2)0.040 (3)0.023 (2)0.004 (2)0.014 (2)
C70.050 (3)0.042 (3)0.033 (3)0.012 (2)0.002 (2)0.013 (2)
C80.051 (3)0.056 (4)0.049 (4)0.015 (3)0.005 (3)0.020 (3)
C90.050 (3)0.053 (4)0.056 (4)0.014 (3)0.001 (3)0.015 (3)
C100.056 (3)0.040 (3)0.055 (4)0.008 (3)0.003 (3)0.019 (3)
C110.055 (3)0.041 (3)0.050 (3)0.015 (3)0.002 (3)0.024 (3)
Geometric parameters (Å, º) top
Au1—N12.035 (5)C4—H40.9300
Au1—Cl12.268 (2)C5—C61.503 (8)
Au1—Cl22.258 (2)C6—C71.388 (8)
Au1—Cl32.280 (2)C6—C111.385 (8)
N1—C11.351 (8)C7—C81.387 (9)
N1—C51.341 (7)C7—H70.9300
C1—C21.367 (8)C8—C91.377 (10)
C1—H10.9300C8—H80.9300
C2—C31.397 (11)C9—C101.382 (10)
C2—H20.9300C9—H90.9300
C3—C41.353 (10)C10—C111.372 (9)
C3—H30.9300C10—H100.9300
C4—C51.378 (8)C11—H110.9300
N1—Au1—Cl190.2 (1)N1—C5—C4119.8 (6)
N1—Au1—Cl2179.6 (1)N1—C5—C6118.5 (5)
N1—Au1—Cl388.9 (1)C4—C5—C6121.7 (5)
Cl1—Au1—Cl290.21 (7)C7—C6—C11119.5 (6)
Cl1—Au1—Cl3177.68 (5)C7—C6—C5121.4 (5)
Cl2—Au1—Cl390.70 (6)C11—C6—C5118.9 (5)
C1—N1—C5119.8 (5)C6—C7—C8120.1 (6)
C1—N1—Au1116.8 (4)C6—C7—H7120.0
C5—N1—Au1122.9 (4)C8—C7—H7120.0
N1—C1—C2122.2 (6)C9—C8—C7120.0 (7)
N1—C1—H1118.9C9—C8—H8120.0
C2—C1—H1118.9C7—C8—H8120.0
C1—C2—C3118.1 (6)C10—C9—C8119.7 (6)
C1—C2—H2121.0C10—C9—H9120.2
C3—C2—H2121.0C8—C9—H9120.2
C4—C3—C2119.0 (6)C9—C10—C11120.8 (6)
C4—C3—H3120.5C9—C10—H10119.6
C2—C3—H3120.5C11—C10—H10119.6
C3—C4—C5121.2 (6)C10—C11—C6119.9 (6)
C3—C4—H4119.4C10—C11—H11120.0
C5—C4—H4119.4C6—C11—H11120.0
Cl1—Au1—N1—C175.5 (4)C3—C4—C5—C6177.4 (6)
Cl3—Au1—N1—C1102.4 (4)N1—C5—C6—C752.6 (7)
Cl1—Au1—N1—C5112.9 (4)C4—C5—C6—C7125.4 (6)
Cl3—Au1—N1—C569.3 (4)N1—C5—C6—C11131.6 (6)
C5—N1—C1—C20.9 (9)C4—C5—C6—C1150.3 (8)
Au1—N1—C1—C2171.1 (5)C11—C6—C7—C81.2 (8)
N1—C1—C2—C31.2 (10)C5—C6—C7—C8174.5 (5)
C1—C2—C3—C42.3 (10)C6—C7—C8—C91.0 (10)
C2—C3—C4—C51.4 (11)C7—C8—C9—C100.2 (10)
C1—N1—C5—C41.8 (8)C8—C9—C10—C110.2 (10)
Au1—N1—C5—C4169.6 (5)C9—C10—C11—C60.1 (10)
C1—N1—C5—C6176.3 (5)C7—C6—C11—C100.8 (9)
Au1—N1—C5—C612.3 (7)C5—C6—C11—C10175.0 (5)
C3—C4—C5—N10.7 (10)

Experimental details

Crystal data
Chemical formula[AuCl3(C11H9N)]
Mr458.51
Crystal system, space groupTriclinic, P1
Temperature (K)298
a, b, c (Å)8.192 (2), 9.078 (2), 10.296 (2)
α, β, γ (°)66.28 (3), 83.74 (3), 68.02 (2)
V3)649.2 (2)
Z2
Radiation typeMo Kα
µ (mm1)11.92
Crystal size (mm)0.29 × 0.24 × 0.18
Data collection
DiffractometerRigaku R-AXIS RAPID IP
diffractometer
Absorption correctionMumerical
(NUMABS; Higashi, 1995)
Tmin, Tmax0.090, 0.223
No. of measured, independent and
observed [I > 2σ(I)] reflections
6439, 2952, 2823
Rint0.022
(sin θ/λ)max1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.022, 0.079, 1.30
No. of reflections2952
No. of parameters145
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)1.06, 0.92

Computer programs: RAPID-AUTO (Rigaku Corporation, 1998), RAPID-AUTO, CrystalStructure (Rigaku/MSC, 2002), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), X-SEED (Barbour, 2001), publCIF (Westrip, 2007).

Selected bond lengths (Å) top
Au1—N12.035 (5)Au1—Cl22.258 (2)
Au1—Cl12.268 (2)Au1—Cl32.280 (2)
 

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