Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807021307/hb2395sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807021307/hb2395Isup2.hkl |
CCDC reference: 650535
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).
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.
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).
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).
Fig. 1. View of the molecular structure of (I) with displacement ellipsoids drawn at the 50% probability level (arbitary spheres for the H atoms). |
[AuCl3(C11H9N)] | Z = 2 |
Mr = 458.51 | F(000) = 424 |
Triclinic, P1 | Dx = 2.346 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 8.192 (2) Å | Cell parameters from 6137 reflections |
b = 9.078 (2) Å | θ = 3.0–27.5° |
c = 10.296 (2) Å | µ = 11.92 mm−1 |
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 |
Rigaku R-AXIS RAPID IP diffractometer | 2952 independent reflections |
Radiation source: fine-focus sealed tube | 2823 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.022 |
ω scan | θmax = 27.5°, θmin = 3.0° |
Absorption correction: mumerical (NUMABS; Higashi, 1995) | h = −10→10 |
Tmin = 0.090, Tmax = 0.223 | k = −11→11 |
6439 measured reflections | l = −13→13 |
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)] = 0.022 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.079 | H-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 parameters | Δρmax = 1.06 e Å−3 |
0 restraints | Δρmin = −0.92 e Å−3 |
[AuCl3(C11H9N)] | γ = 68.02 (2)° |
Mr = 458.51 | V = 649.2 (2) Å3 |
Triclinic, P1 | Z = 2 |
a = 8.192 (2) Å | Mo Kα radiation |
b = 9.078 (2) Å | µ = 11.92 mm−1 |
c = 10.296 (2) Å | T = 298 K |
α = 66.28 (3)° | 0.29 × 0.24 × 0.18 mm |
β = 83.74 (3)° |
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 = 0.223 | Rint = 0.022 |
6439 measured reflections |
R[F2 > 2σ(F2)] = 0.022 | 0 restraints |
wR(F2) = 0.079 | H-atom parameters constrained |
S = 1.30 | Δρmax = 1.06 e Å−3 |
2952 reflections | Δρmin = −0.92 e Å−3 |
145 parameters |
x | y | z | Uiso*/Ueq | ||
Au1 | 0.60793 (2) | 0.81841 (2) | 0.703793 (18) | 0.03193 (9) | |
Cl1 | 0.4693 (2) | 0.8672 (3) | 0.8937 (2) | 0.0564 (4) | |
Cl2 | 0.7651 (2) | 0.9810 (2) | 0.6926 (2) | 0.0524 (4) | |
Cl3 | 0.7367 (2) | 0.7757 (2) | 0.50767 (17) | 0.0468 (3) | |
N1 | 0.4665 (6) | 0.6723 (6) | 0.7124 (5) | 0.0387 (10) | |
C1 | 0.2963 (7) | 0.7577 (8) | 0.6642 (7) | 0.0450 (12) | |
H1 | 0.2464 | 0.8759 | 0.6421 | 0.054* | |
C2 | 0.1949 (8) | 0.6762 (10) | 0.6468 (7) | 0.0528 (15) | |
H2 | 0.0772 | 0.7368 | 0.6151 | 0.063* | |
C3 | 0.2731 (10) | 0.4994 (11) | 0.6779 (8) | 0.0597 (18) | |
H3 | 0.2095 | 0.4404 | 0.6642 | 0.072* | |
C4 | 0.4429 (9) | 0.4153 (9) | 0.7283 (7) | 0.0519 (14) | |
H4 | 0.4949 | 0.2971 | 0.7512 | 0.062* | |
C5 | 0.5401 (8) | 0.5015 (7) | 0.7465 (6) | 0.0406 (11) | |
C6 | 0.7262 (7) | 0.4083 (7) | 0.8082 (6) | 0.0384 (11) | |
C7 | 0.7772 (8) | 0.4233 (7) | 0.9251 (6) | 0.0435 (12) | |
H7 | 0.6982 | 0.4997 | 0.9619 | 0.052* | |
C8 | 0.9457 (9) | 0.3244 (9) | 0.9872 (8) | 0.0527 (14) | |
H8 | 0.9791 | 0.3332 | 1.0664 | 0.063* | |
C9 | 1.0635 (9) | 0.2131 (9) | 0.9316 (8) | 0.0563 (16) | |
H9 | 1.1768 | 0.1469 | 0.9728 | 0.068* | |
C10 | 1.0126 (9) | 0.2001 (8) | 0.8141 (8) | 0.0532 (15) | |
H10 | 1.0924 | 0.1251 | 0.7765 | 0.064* | |
C11 | 0.8458 (8) | 0.2966 (7) | 0.7525 (7) | 0.0470 (13) | |
H11 | 0.8131 | 0.2870 | 0.6734 | 0.056* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Au1 | 0.03303 (12) | 0.02905 (12) | 0.03363 (13) | −0.00925 (8) | −0.00320 (8) | −0.01286 (8) |
Cl1 | 0.0579 (9) | 0.0643 (10) | 0.0499 (9) | −0.0134 (8) | 0.0078 (7) | −0.0345 (8) |
Cl2 | 0.0608 (9) | 0.0451 (7) | 0.0611 (10) | −0.0273 (7) | −0.0070 (7) | −0.0205 (7) |
Cl3 | 0.0538 (8) | 0.0525 (8) | 0.0415 (8) | −0.0237 (7) | 0.0098 (6) | −0.0235 (6) |
N1 | 0.042 (2) | 0.045 (2) | 0.037 (2) | −0.023 (2) | 0.0048 (19) | −0.018 (2) |
C1 | 0.040 (3) | 0.054 (3) | 0.043 (3) | −0.018 (3) | 0.000 (2) | −0.020 (3) |
C2 | 0.040 (3) | 0.076 (4) | 0.049 (4) | −0.029 (3) | 0.000 (3) | −0.024 (3) |
C3 | 0.072 (4) | 0.077 (5) | 0.060 (4) | −0.053 (4) | 0.010 (3) | −0.034 (4) |
C4 | 0.063 (4) | 0.047 (3) | 0.054 (4) | −0.030 (3) | −0.002 (3) | −0.018 (3) |
C5 | 0.051 (3) | 0.044 (3) | 0.032 (3) | −0.023 (2) | 0.001 (2) | −0.014 (2) |
C6 | 0.048 (3) | 0.034 (2) | 0.040 (3) | −0.023 (2) | 0.004 (2) | −0.014 (2) |
C7 | 0.050 (3) | 0.042 (3) | 0.033 (3) | −0.012 (2) | −0.002 (2) | −0.013 (2) |
C8 | 0.051 (3) | 0.056 (4) | 0.049 (4) | −0.015 (3) | −0.005 (3) | −0.020 (3) |
C9 | 0.050 (3) | 0.053 (4) | 0.056 (4) | −0.014 (3) | −0.001 (3) | −0.015 (3) |
C10 | 0.056 (3) | 0.040 (3) | 0.055 (4) | −0.008 (3) | 0.003 (3) | −0.019 (3) |
C11 | 0.055 (3) | 0.041 (3) | 0.050 (3) | −0.015 (3) | 0.002 (3) | −0.024 (3) |
Au1—N1 | 2.035 (5) | C4—H4 | 0.9300 |
Au1—Cl1 | 2.268 (2) | C5—C6 | 1.503 (8) |
Au1—Cl2 | 2.258 (2) | C6—C7 | 1.388 (8) |
Au1—Cl3 | 2.280 (2) | C6—C11 | 1.385 (8) |
N1—C1 | 1.351 (8) | C7—C8 | 1.387 (9) |
N1—C5 | 1.341 (7) | C7—H7 | 0.9300 |
C1—C2 | 1.367 (8) | C8—C9 | 1.377 (10) |
C1—H1 | 0.9300 | C8—H8 | 0.9300 |
C2—C3 | 1.397 (11) | C9—C10 | 1.382 (10) |
C2—H2 | 0.9300 | C9—H9 | 0.9300 |
C3—C4 | 1.353 (10) | C10—C11 | 1.372 (9) |
C3—H3 | 0.9300 | C10—H10 | 0.9300 |
C4—C5 | 1.378 (8) | C11—H11 | 0.9300 |
N1—Au1—Cl1 | 90.2 (1) | N1—C5—C4 | 119.8 (6) |
N1—Au1—Cl2 | 179.6 (1) | N1—C5—C6 | 118.5 (5) |
N1—Au1—Cl3 | 88.9 (1) | C4—C5—C6 | 121.7 (5) |
Cl1—Au1—Cl2 | 90.21 (7) | C7—C6—C11 | 119.5 (6) |
Cl1—Au1—Cl3 | 177.68 (5) | C7—C6—C5 | 121.4 (5) |
Cl2—Au1—Cl3 | 90.70 (6) | C11—C6—C5 | 118.9 (5) |
C1—N1—C5 | 119.8 (5) | C6—C7—C8 | 120.1 (6) |
C1—N1—Au1 | 116.8 (4) | C6—C7—H7 | 120.0 |
C5—N1—Au1 | 122.9 (4) | C8—C7—H7 | 120.0 |
N1—C1—C2 | 122.2 (6) | C9—C8—C7 | 120.0 (7) |
N1—C1—H1 | 118.9 | C9—C8—H8 | 120.0 |
C2—C1—H1 | 118.9 | C7—C8—H8 | 120.0 |
C1—C2—C3 | 118.1 (6) | C10—C9—C8 | 119.7 (6) |
C1—C2—H2 | 121.0 | C10—C9—H9 | 120.2 |
C3—C2—H2 | 121.0 | C8—C9—H9 | 120.2 |
C4—C3—C2 | 119.0 (6) | C9—C10—C11 | 120.8 (6) |
C4—C3—H3 | 120.5 | C9—C10—H10 | 119.6 |
C2—C3—H3 | 120.5 | C11—C10—H10 | 119.6 |
C3—C4—C5 | 121.2 (6) | C10—C11—C6 | 119.9 (6) |
C3—C4—H4 | 119.4 | C10—C11—H11 | 120.0 |
C5—C4—H4 | 119.4 | C6—C11—H11 | 120.0 |
Cl1—Au1—N1—C1 | 75.5 (4) | C3—C4—C5—C6 | 177.4 (6) |
Cl3—Au1—N1—C1 | −102.4 (4) | N1—C5—C6—C7 | 52.6 (7) |
Cl1—Au1—N1—C5 | −112.9 (4) | C4—C5—C6—C7 | −125.4 (6) |
Cl3—Au1—N1—C5 | 69.3 (4) | N1—C5—C6—C11 | −131.6 (6) |
C5—N1—C1—C2 | −0.9 (9) | C4—C5—C6—C11 | 50.3 (8) |
Au1—N1—C1—C2 | 171.1 (5) | C11—C6—C7—C8 | −1.2 (8) |
N1—C1—C2—C3 | −1.2 (10) | C5—C6—C7—C8 | 174.5 (5) |
C1—C2—C3—C4 | 2.3 (10) | C6—C7—C8—C9 | 1.0 (10) |
C2—C3—C4—C5 | −1.4 (11) | C7—C8—C9—C10 | −0.2 (10) |
C1—N1—C5—C4 | 1.8 (8) | C8—C9—C10—C11 | −0.2 (10) |
Au1—N1—C5—C4 | −169.6 (5) | C9—C10—C11—C6 | −0.1 (10) |
C1—N1—C5—C6 | −176.3 (5) | C7—C6—C11—C10 | 0.8 (9) |
Au1—N1—C5—C6 | 12.3 (7) | C5—C6—C11—C10 | −175.0 (5) |
C3—C4—C5—N1 | −0.7 (10) |
Experimental details
Crystal data | |
Chemical formula | [AuCl3(C11H9N)] |
Mr | 458.51 |
Crystal system, space group | Triclinic, 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) |
V (Å3) | 649.2 (2) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 11.92 |
Crystal size (mm) | 0.29 × 0.24 × 0.18 |
Data collection | |
Diffractometer | Rigaku R-AXIS RAPID IP diffractometer |
Absorption correction | Mumerical (NUMABS; Higashi, 1995) |
Tmin, Tmax | 0.090, 0.223 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 6439, 2952, 2823 |
Rint | 0.022 |
(sin θ/λ)max (Å−1) | 0.650 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.022, 0.079, 1.30 |
No. of reflections | 2952 |
No. of parameters | 145 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 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).
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).