Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536812050404/yk2081sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536812050404/yk2081Isup2.hkl |
CCDC reference: 920193
Key indicators
- Single-crystal X-ray study
- T = 173 K
- Mean (C-C) = 0.009 Å
- Disorder in main residue
- R factor = 0.039
- wR factor = 0.100
- Data-to-parameter ratio = 18.5
checkCIF/PLATON results
No syntax errors found
Alert level A PLAT973_ALERT_2_A Large Calcd. Positive Residual Density on Au2 2.08 eA-3
Author Response: This peak lies at 0.05 A from the Au2 atom and it cannot be approximated by any additional atom or by the disorder in Au2. This is apparently due to anomalous dispersion effects. The similar instance also emerged in a recent issue of Acta Cryst., E (F.Liu and F.Zhang, <i>Acta Cryst.</i>, 2011, E67, m525). The complex investigated here had a Sm atom which is significantly lighter than the Au atom. |
Alert level C PLAT342_ALERT_3_C Low Bond Precision on C-C Bonds ............... 0.0086 Ang PLAT910_ALERT_3_C Missing # of FCF Reflections Below Th(Min) ..... 6 PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L= 0.600 4 PLAT971_ALERT_2_C Large Calcd. Non-Metal Positive Residual Density 1.59 eA-3 PLAT971_ALERT_2_C Large Calcd. Non-Metal Positive Residual Density 1.55 eA-3 PLAT975_ALERT_2_C Positive Residual Density at 0.97A from N23 . 0.46 eA-3
Alert level G PLAT003_ALERT_2_G Number of Uiso or Uij Restrained Atom Sites .... 30 PLAT005_ALERT_5_G No _iucr_refine_instructions_details in the CIF ? PLAT128_ALERT_4_G Alternate Setting of Space-group P21/c ....... P21/n PLAT301_ALERT_3_G Note: Main Residue Disorder ................... 14 Perc. PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 240 PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L= 0.600 7 PLAT960_ALERT_3_G Number of Intensities with I .LT. - 2*sig(I) ... 3
1 ALERT level A = Most likely a serious problem - resolve or explain 0 ALERT level B = A potentially serious problem, consider carefully 6 ALERT level C = Check. Ensure it is not caused by an omission or oversight 7 ALERT level G = General information/check it is not something unexpected 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 5 ALERT type 2 Indicator that the structure model may be wrong or deficient 6 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion 1 ALERT type 5 Informative message, check
To a dry CH2Cl2 (10 ml) solution of the precursor [Au(tht)Cl] (tht = tetrahydrothiophene) was added an equimolar amount of N-{(E)-[2-(diphenylphosphanyl)phenyl]methylidene}-2-furan-2-ylethanamine in CH2Cl2 (10 ml), and stirred at room temperature for 2 hrs. The solvent was reduced under reduced pressure and on addition of hexane, the product was filtered off and washed with Et2O (2 X 5 ml)and dried under vacuum for 4 hrs affording a yellow precipitate. Crystals suitable for X-ray structure determination were obtained by recrystallization from a CH2Cl2-hexane mixture at room temperature.
The methine and aromatic H atoms were placed in geometrically idealized positions and constrained to ride on their parent atoms, with with C—H = 0.95 Å and Uiso(H) = 1.2Ueq(C) for aromatic, C—H = 0.99 Å and Uiso(H) = 1.2Ueq(C) for CH2 C—H = 0.95 Å and Uiso(H) = 1.2Ueq(C) for CH. A disorder refinement model was applied to the furyl ring in the asymmetric unit. Geometrical (FLAT) restaraints were applied to keep the ring planar.Bond distance (DFIX) and distance similarity restraints (SADI) were applied to obtain reasonable geometries. Ellipsoid displacement (SIMU and DELU) restraints were also applied to the disordered moiety. Free variables were connected to the disordered component to add to unity.
There is a growing interest in the co-ordination chemistry of ligands containing both hard (N donor) and soft (P donor) Lewis bases. Such ligands have the potential to bind to soft metal centers such as those of the platinum group metals strongly via phosphorus and weakly via nitrogen, which allows for the displacement of the chelating N-moiety. This is very desirable in homogenous catalytic reactions and the catalytic application of P—N based ligands is being thoroughly investigated by our group.
Among the 'hard' donor type atoms, the co-ordination chemistry of gold(I) shows a distinct paucity in the literature. In this scenario the potentially bidentate ligand is chelated to the metal through only the phosphorus atom (Fig. 1). The gold complex showed a closely linear P— Au—Cl system (bond angle of 176.49°). Another important geometrical parameter includes the C22—N23 = 1.254 (6) Å which is consistent with C=N double bonding. The Au—P bond distance of 2.2321 (13) Å agrees with that reported by Williams et al..
For general background to the title compound, see: Shaw (1999); Barnard et al. (2004); Nomiya et al. (2003). For the synthesis of the starting materials, see: Mogorosi et al. (2011); Uson & Laguna (1986). For similar compounds, see: Chiririwa & Muller (2012); Williams et al. (2007). For their applications, see: Chiririwa et al. (2013).
Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT and XPREP (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg & Putz, 2005); software used to prepare material for publication: WinGX (Farrugia, 2012).
Fig. 1. View of [Au(C24H20NOP)Cl] showing the atom labelling scheme and displacement ellipsoids drawn at the 40% probability level. |
[AuCl(C24H20NOP)] | F(000) = 1160 |
Mr = 601.80 | Dx = 1.783 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 5534 reflections |
a = 13.4559 (4) Å | θ = 3.6–28.3° |
b = 10.3917 (2) Å | µ = 6.77 mm−1 |
c = 17.2641 (4) Å | T = 173 K |
β = 111.751 (1)° | Plate, yellow |
V = 2242.16 (9) Å3 | 0.16 × 0.11 × 0.02 mm |
Z = 4 |
Bruker APEXII 4K CCD diffractometer | 5536 independent reflections |
Radiation source: fine-focus sealed tube | 4175 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.100 |
Detector resolution: 0 pixels mm-1 | θmax = 28.3°, θmin = 3.1° |
0.5° ω scans, 20s | h = −17→17 |
Absorption correction: multi-scan (SADABS; Bruker, 2007) | k = −13→13 |
Tmin = 0.411, Tmax = 0.877 | l = −23→23 |
74340 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)] = 0.039 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.100 | H-atom parameters constrained |
S = 1.07 | w = 1/[σ2(Fo2) + (0.0574P)2] where P = (Fo2 + 2Fc2)/3 |
5536 reflections | (Δ/σ)max = 0.003 |
299 parameters | Δρmax = 2.27 e Å−3 |
240 restraints | Δρmin = −1.52 e Å−3 |
[AuCl(C24H20NOP)] | V = 2242.16 (9) Å3 |
Mr = 601.80 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 13.4559 (4) Å | µ = 6.77 mm−1 |
b = 10.3917 (2) Å | T = 173 K |
c = 17.2641 (4) Å | 0.16 × 0.11 × 0.02 mm |
β = 111.751 (1)° |
Bruker APEXII 4K CCD diffractometer | 5536 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2007) | 4175 reflections with I > 2σ(I) |
Tmin = 0.411, Tmax = 0.877 | Rint = 0.100 |
74340 measured reflections |
R[F2 > 2σ(F2)] = 0.039 | 240 restraints |
wR(F2) = 0.100 | H-atom parameters constrained |
S = 1.07 | Δρmax = 2.27 e Å−3 |
5536 reflections | Δρmin = −1.52 e Å−3 |
299 parameters |
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 | Occ. (<1) | |
Cl1 | 0.67118 (12) | −0.07954 (12) | 0.82704 (9) | 0.0504 (3) | |
Au2 | 0.537496 (15) | 0.068557 (17) | 0.801052 (11) | 0.03605 (9) | |
P3 | 0.40775 (10) | 0.21597 (12) | 0.76820 (7) | 0.0330 (3) | |
C4 | 0.3211 (4) | 0.1963 (5) | 0.8271 (3) | 0.0402 (11) | |
C5 | 0.2133 (4) | 0.2276 (6) | 0.7948 (4) | 0.0525 (14) | |
H5 | 0.1813 | 0.2570 | 0.7389 | 0.063* | |
C6 | 0.1517 (6) | 0.2161 (7) | 0.8440 (5) | 0.0707 (19) | |
H6 | 0.0775 | 0.2361 | 0.8213 | 0.085* | |
C7 | 0.1992 (7) | 0.1753 (6) | 0.9262 (5) | 0.075 (2) | |
H7 | 0.1576 | 0.1680 | 0.9600 | 0.090* | |
C8 | 0.3059 (7) | 0.1456 (6) | 0.9584 (4) | 0.0696 (19) | |
H8 | 0.3384 | 0.1187 | 1.0148 | 0.084* | |
C9 | 0.3670 (5) | 0.1546 (5) | 0.9092 (3) | 0.0543 (14) | |
H9 | 0.4406 | 0.1320 | 0.9318 | 0.065* | |
C10 | 0.3191 (4) | 0.2085 (5) | 0.6596 (3) | 0.0342 (10) | |
C11 | 0.2655 (4) | 0.3144 (5) | 0.6159 (3) | 0.0477 (13) | |
H11 | 0.2723 | 0.3954 | 0.6429 | 0.057* | |
C12 | 0.2017 (5) | 0.3020 (6) | 0.5326 (4) | 0.0626 (17) | |
H12 | 0.1644 | 0.3750 | 0.5026 | 0.075* | |
C13 | 0.1913 (5) | 0.1858 (6) | 0.4923 (3) | 0.0588 (16) | |
H13 | 0.1469 | 0.1788 | 0.4350 | 0.071* | |
C14 | 0.2447 (5) | 0.0805 (6) | 0.5347 (4) | 0.0561 (16) | |
H14 | 0.2395 | 0.0006 | 0.5068 | 0.067* | |
C15 | 0.3072 (4) | 0.0910 (5) | 0.6195 (3) | 0.0436 (12) | |
H15 | 0.3418 | 0.0169 | 0.6499 | 0.052* | |
C16 | 0.4594 (4) | 0.3787 (5) | 0.7951 (3) | 0.0326 (10) | |
C17 | 0.4287 (4) | 0.4506 (4) | 0.8500 (3) | 0.0373 (11) | |
H17 | 0.3743 | 0.4178 | 0.8672 | 0.045* | |
C18 | 0.4745 (5) | 0.5690 (4) | 0.8810 (4) | 0.0463 (13) | |
H18 | 0.4517 | 0.6157 | 0.9187 | 0.056* | |
C19 | 0.5530 (5) | 0.6175 (5) | 0.8564 (4) | 0.0522 (14) | |
H19 | 0.5860 | 0.6974 | 0.8778 | 0.063* | |
C20 | 0.5835 (5) | 0.5500 (5) | 0.8009 (4) | 0.0499 (14) | |
H20 | 0.6372 | 0.5856 | 0.7839 | 0.060* | |
C21 | 0.5394 (4) | 0.4311 (4) | 0.7681 (3) | 0.0392 (11) | |
C22 | 0.5774 (4) | 0.3688 (6) | 0.7093 (3) | 0.0458 (12) | |
H22 | 0.6342 | 0.4075 | 0.6977 | 0.055* | |
N23 | 0.5382 (3) | 0.2656 (4) | 0.6732 (3) | 0.0441 (10) | |
C24 | 0.5800 (5) | 0.2119 (7) | 0.6128 (4) | 0.0604 (16) | |
H24A | 0.5925 | 0.1184 | 0.6225 | 0.072* | |
H24B | 0.6490 | 0.2533 | 0.6197 | 0.072* | |
C25 | 0.5007 (5) | 0.2348 (6) | 0.5259 (4) | 0.0577 (15) | |
C26 | 0.478 (2) | 0.354 (2) | 0.5111 (14) | 0.069 (4) | 0.51 (2) |
H26 | 0.5032 | 0.4279 | 0.5455 | 0.082* | 0.51 (2) |
C27 | 0.4039 (18) | 0.344 (2) | 0.4285 (13) | 0.077 (4) | 0.51 (2) |
H27 | 0.3607 | 0.4145 | 0.3999 | 0.092* | 0.51 (2) |
C28 | 0.399 (2) | 0.235 (2) | 0.3948 (16) | 0.075 (5) | 0.51 (2) |
H28 | 0.3521 | 0.2068 | 0.3413 | 0.090* | 0.51 (2) |
O29 | 0.4960 (14) | 0.151 (2) | 0.4681 (13) | 0.062 (4) | 0.51 (2) |
C28A | 0.3720 (18) | 0.3008 (19) | 0.4016 (13) | 0.058 (4) | 0.49 (2) |
H28A | 0.3158 | 0.3466 | 0.3607 | 0.070* | 0.49 (2) |
C27A | 0.418 (2) | 0.1871 (19) | 0.3925 (15) | 0.066 (4) | 0.49 (2) |
H27A | 0.4114 | 0.1472 | 0.3413 | 0.079* | 0.49 (2) |
C26A | 0.466 (3) | 0.150 (5) | 0.457 (3) | 0.070 (5) | 0.49 (2) |
H26A | 0.4823 | 0.0607 | 0.4651 | 0.084* | 0.49 (2) |
O29A | 0.4309 (12) | 0.3359 (15) | 0.4912 (11) | 0.072 (4) | 0.49 (2) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.0522 (8) | 0.0505 (8) | 0.0493 (8) | 0.0131 (6) | 0.0198 (7) | 0.0090 (6) |
Au2 | 0.03944 (13) | 0.03606 (13) | 0.02786 (12) | 0.00058 (8) | 0.00691 (8) | 0.00152 (8) |
P3 | 0.0335 (6) | 0.0360 (7) | 0.0249 (6) | −0.0020 (5) | 0.0057 (5) | 0.0002 (5) |
C4 | 0.054 (3) | 0.036 (3) | 0.033 (3) | −0.013 (2) | 0.019 (2) | −0.007 (2) |
C5 | 0.048 (3) | 0.062 (4) | 0.053 (3) | −0.019 (3) | 0.025 (3) | −0.016 (3) |
C6 | 0.074 (4) | 0.075 (4) | 0.079 (5) | −0.032 (4) | 0.047 (4) | −0.038 (4) |
C7 | 0.108 (5) | 0.067 (4) | 0.082 (5) | −0.039 (4) | 0.073 (5) | −0.034 (4) |
C8 | 0.128 (6) | 0.049 (4) | 0.048 (4) | −0.021 (4) | 0.051 (4) | −0.010 (3) |
C9 | 0.081 (4) | 0.048 (3) | 0.036 (3) | −0.009 (3) | 0.024 (3) | −0.003 (2) |
C10 | 0.032 (2) | 0.039 (3) | 0.026 (2) | −0.011 (2) | 0.0051 (19) | −0.001 (2) |
C11 | 0.054 (3) | 0.044 (3) | 0.033 (3) | −0.008 (2) | 0.002 (2) | 0.001 (2) |
C12 | 0.059 (4) | 0.064 (4) | 0.044 (3) | −0.012 (3) | −0.005 (3) | 0.011 (3) |
C13 | 0.054 (3) | 0.080 (4) | 0.030 (3) | −0.021 (3) | 0.000 (3) | −0.002 (3) |
C14 | 0.053 (4) | 0.066 (4) | 0.040 (3) | −0.014 (3) | 0.007 (3) | −0.017 (3) |
C15 | 0.041 (3) | 0.045 (3) | 0.040 (3) | −0.004 (2) | 0.009 (2) | −0.007 (2) |
C16 | 0.030 (2) | 0.036 (2) | 0.025 (2) | 0.000 (2) | 0.0021 (19) | 0.002 (2) |
C17 | 0.033 (3) | 0.033 (3) | 0.041 (3) | −0.0011 (19) | 0.008 (2) | −0.002 (2) |
C18 | 0.052 (3) | 0.039 (3) | 0.041 (3) | 0.004 (2) | 0.009 (3) | −0.004 (2) |
C19 | 0.062 (4) | 0.036 (3) | 0.047 (3) | −0.011 (3) | 0.007 (3) | −0.003 (3) |
C20 | 0.053 (3) | 0.046 (3) | 0.043 (3) | −0.007 (2) | 0.008 (3) | 0.002 (2) |
C21 | 0.039 (3) | 0.044 (3) | 0.028 (2) | −0.004 (2) | 0.004 (2) | 0.005 (2) |
C22 | 0.042 (3) | 0.056 (3) | 0.038 (3) | −0.010 (3) | 0.014 (2) | 0.002 (3) |
N23 | 0.040 (2) | 0.057 (3) | 0.036 (2) | −0.007 (2) | 0.015 (2) | 0.003 (2) |
C24 | 0.067 (4) | 0.066 (4) | 0.049 (3) | −0.013 (3) | 0.022 (3) | −0.012 (3) |
C25 | 0.070 (4) | 0.062 (4) | 0.046 (3) | −0.017 (3) | 0.027 (3) | −0.005 (3) |
C26 | 0.088 (10) | 0.069 (9) | 0.044 (8) | 0.000 (9) | 0.020 (8) | 0.002 (7) |
C27 | 0.091 (9) | 0.090 (9) | 0.048 (9) | 0.006 (8) | 0.025 (8) | 0.007 (8) |
C28 | 0.089 (9) | 0.080 (10) | 0.045 (7) | −0.008 (9) | 0.012 (7) | 0.000 (9) |
O29 | 0.082 (9) | 0.059 (5) | 0.038 (7) | −0.008 (8) | 0.016 (7) | −0.011 (5) |
C28A | 0.075 (8) | 0.061 (9) | 0.044 (8) | −0.003 (7) | 0.026 (6) | 0.003 (7) |
C27A | 0.092 (9) | 0.069 (9) | 0.036 (6) | −0.011 (8) | 0.022 (6) | −0.005 (7) |
C26A | 0.084 (11) | 0.064 (8) | 0.044 (8) | −0.013 (9) | 0.005 (8) | −0.004 (7) |
O29A | 0.077 (8) | 0.076 (7) | 0.063 (8) | −0.008 (6) | 0.026 (7) | 0.010 (6) |
Cl1—Au2 | 2.2820 (13) | C17—H17 | 0.9500 |
Au2—P3 | 2.2321 (13) | C18—C19 | 1.371 (8) |
P3—C10 | 1.813 (5) | C18—H18 | 0.9500 |
P3—C4 | 1.821 (5) | C19—C20 | 1.368 (8) |
P3—C16 | 1.822 (5) | C19—H19 | 0.9500 |
C4—C5 | 1.386 (7) | C20—C21 | 1.397 (7) |
C4—C9 | 1.389 (7) | C20—H20 | 0.9500 |
C5—C6 | 1.394 (8) | C21—C22 | 1.446 (8) |
C5—H5 | 0.9500 | C22—N23 | 1.254 (6) |
C6—C7 | 1.390 (10) | C22—H22 | 0.9500 |
C6—H6 | 0.9500 | N23—C24 | 1.467 (7) |
C7—C8 | 1.370 (10) | C24—C25 | 1.503 (9) |
C7—H7 | 0.9500 | C24—H24A | 0.9900 |
C8—C9 | 1.386 (8) | C24—H24B | 0.9900 |
C8—H8 | 0.9500 | C25—C26 | 1.28 (2) |
C9—H9 | 0.9500 | C25—O29 | 1.30 (2) |
C10—C11 | 1.377 (7) | C25—O29A | 1.388 (17) |
C10—C15 | 1.384 (7) | C25—C26A | 1.41 (4) |
C11—C12 | 1.381 (7) | C26—C27 | 1.41 (3) |
C11—H11 | 0.9500 | C26—H26 | 0.9500 |
C12—C13 | 1.374 (8) | C27—C28 | 1.27 (3) |
C12—H12 | 0.9500 | C27—H27 | 0.9500 |
C13—C14 | 1.364 (8) | C28—O29 | 1.68 (4) |
C13—H13 | 0.9500 | C28—H28 | 0.9500 |
C14—C15 | 1.396 (7) | C28A—C27A | 1.37 (3) |
C14—H14 | 0.9500 | C28A—O29A | 1.50 (2) |
C15—H15 | 0.9500 | C28A—H28A | 0.9500 |
C16—C17 | 1.385 (7) | C27A—C26A | 1.13 (5) |
C16—C21 | 1.430 (7) | C27A—H27A | 0.9500 |
C17—C18 | 1.391 (6) | C26A—H26A | 0.9500 |
P3—Au2—Cl1 | 176.49 (5) | C19—C18—H18 | 120.4 |
C10—P3—C4 | 105.1 (2) | C17—C18—H18 | 120.4 |
C10—P3—C16 | 110.2 (2) | C20—C19—C18 | 119.6 (5) |
C4—P3—C16 | 103.0 (2) | C20—C19—H19 | 120.2 |
C10—P3—Au2 | 112.74 (17) | C18—C19—H19 | 120.2 |
C4—P3—Au2 | 112.53 (18) | C19—C20—C21 | 123.1 (6) |
C16—P3—Au2 | 112.55 (15) | C19—C20—H20 | 118.5 |
C5—C4—C9 | 119.1 (5) | C21—C20—H20 | 118.5 |
C5—C4—P3 | 122.7 (4) | C20—C21—C16 | 117.5 (5) |
C9—C4—P3 | 118.1 (4) | C20—C21—C22 | 118.3 (5) |
C4—C5—C6 | 120.3 (6) | C16—C21—C22 | 124.2 (4) |
C4—C5—H5 | 119.8 | N23—C22—C21 | 122.6 (5) |
C6—C5—H5 | 119.8 | N23—C22—H22 | 118.7 |
C7—C6—C5 | 119.7 (7) | C21—C22—H22 | 118.7 |
C7—C6—H6 | 120.1 | C22—N23—C24 | 118.5 (5) |
C5—C6—H6 | 120.1 | N23—C24—C25 | 109.4 (5) |
C8—C7—C6 | 120.0 (6) | N23—C24—H24A | 109.8 |
C8—C7—H7 | 120.0 | C25—C24—H24A | 109.8 |
C6—C7—H7 | 120.0 | N23—C24—H24B | 109.8 |
C7—C8—C9 | 120.4 (6) | C25—C24—H24B | 109.8 |
C7—C8—H8 | 119.8 | H24A—C24—H24B | 108.2 |
C9—C8—H8 | 119.8 | C26—C25—O29 | 123.5 (16) |
C8—C9—C4 | 120.4 (6) | O29—C25—O29A | 109.9 (13) |
C8—C9—H9 | 119.8 | C26—C25—C26A | 117 (2) |
C4—C9—H9 | 119.8 | O29A—C25—C26A | 98.6 (19) |
C11—C10—C15 | 119.4 (5) | C26—C25—C24 | 112.4 (12) |
C11—C10—P3 | 122.9 (4) | O29—C25—C24 | 118.2 (11) |
C15—C10—P3 | 117.7 (4) | O29A—C25—C24 | 131.8 (9) |
C10—C11—C12 | 119.6 (5) | C26A—C25—C24 | 129.2 (18) |
C10—C11—H11 | 120.2 | C25—C26—C27 | 98.9 (17) |
C12—C11—H11 | 120.2 | C25—C26—H26 | 130.5 |
C13—C12—C11 | 121.1 (6) | C27—C26—H26 | 130.5 |
C13—C12—H12 | 119.5 | C28—C27—C26 | 115 (2) |
C11—C12—H12 | 119.5 | C28—C27—H27 | 122.3 |
C14—C13—C12 | 119.9 (5) | C26—C27—H27 | 122.3 |
C14—C13—H13 | 120.1 | C27—C28—O29 | 102.9 (19) |
C12—C13—H13 | 120.1 | C27—C28—H28 | 128.6 |
C13—C14—C15 | 119.6 (5) | O29—C28—H28 | 128.6 |
C13—C14—H14 | 120.2 | C25—O29—C28 | 92.1 (17) |
C15—C14—H14 | 120.2 | C27A—C28A—O29A | 103.8 (18) |
C10—C15—C14 | 120.4 (5) | C27A—C28A—H28A | 128.1 |
C10—C15—H15 | 119.8 | O29A—C28A—H28A | 128.1 |
C14—C15—H15 | 119.8 | C26A—C27A—C28A | 107 (3) |
C17—C16—C21 | 118.0 (4) | C26A—C27A—H27A | 126.3 |
C17—C16—P3 | 119.5 (4) | C28A—C27A—H27A | 126.3 |
C21—C16—P3 | 122.2 (4) | C27A—C26A—C25 | 120 (4) |
C16—C17—C18 | 122.6 (5) | C27A—C26A—H26A | 119.8 |
C16—C17—H17 | 118.7 | C25—C26A—H26A | 119.8 |
C18—C17—H17 | 118.7 | C25—O29A—C28A | 106.0 (13) |
C19—C18—C17 | 119.2 (5) | ||
C10—P3—C4—C5 | −25.0 (5) | C18—C19—C20—C21 | −1.0 (9) |
C16—P3—C4—C5 | 90.5 (5) | C19—C20—C21—C16 | −0.6 (8) |
Au2—P3—C4—C5 | −148.1 (4) | C19—C20—C21—C22 | 179.6 (5) |
C10—P3—C4—C9 | 158.5 (4) | C17—C16—C21—C20 | 1.8 (7) |
C16—P3—C4—C9 | −86.0 (4) | P3—C16—C21—C20 | −171.8 (4) |
Au2—P3—C4—C9 | 35.4 (4) | C17—C16—C21—C22 | −178.3 (5) |
C9—C4—C5—C6 | −0.6 (8) | P3—C16—C21—C22 | 8.0 (7) |
P3—C4—C5—C6 | −177.1 (4) | C20—C21—C22—N23 | −175.9 (5) |
C4—C5—C6—C7 | 1.2 (9) | C16—C21—C22—N23 | 4.3 (8) |
C5—C6—C7—C8 | −0.5 (9) | C21—C22—N23—C24 | 178.2 (5) |
C6—C7—C8—C9 | −0.8 (9) | C22—N23—C24—C25 | −105.0 (6) |
C7—C8—C9—C4 | 1.3 (9) | N23—C24—C25—C26 | 56.6 (14) |
C5—C4—C9—C8 | −0.6 (8) | N23—C24—C25—O29 | −149.6 (13) |
P3—C4—C9—C8 | 176.0 (4) | N23—C24—C25—O29A | 34.5 (12) |
C4—P3—C10—C11 | 85.8 (5) | N23—C24—C25—C26A | −136 (2) |
C16—P3—C10—C11 | −24.6 (5) | O29—C25—C26—C27 | 28 (2) |
Au2—P3—C10—C11 | −151.3 (4) | O29A—C25—C26—C27 | −38 (3) |
C4—P3—C10—C15 | −95.4 (4) | C26A—C25—C26—C27 | 12 (3) |
C16—P3—C10—C15 | 154.3 (4) | C24—C25—C26—C27 | −179.4 (11) |
Au2—P3—C10—C15 | 27.6 (4) | C25—C26—C27—C28 | −11 (3) |
C15—C10—C11—C12 | −0.8 (8) | C26—C27—C28—O29 | −4 (3) |
P3—C10—C11—C12 | 178.1 (4) | C26—C25—O29—C28 | −29 (2) |
C10—C11—C12—C13 | −0.3 (9) | O29A—C25—O29—C28 | −2.8 (17) |
C11—C12—C13—C14 | −0.2 (10) | C26A—C25—O29—C28 | 42 (11) |
C12—C13—C14—C15 | 1.9 (9) | C24—C25—O29—C28 | −179.6 (11) |
C11—C10—C15—C14 | 2.4 (8) | C27—C28—O29—C25 | 17 (2) |
P3—C10—C15—C14 | −176.5 (4) | O29A—C28A—C27A—C26A | 15 (3) |
C13—C14—C15—C10 | −3.0 (9) | C28A—C27A—C26A—C25 | −22 (5) |
C10—P3—C16—C17 | 112.4 (4) | C26—C25—C26A—C27A | −1 (5) |
C4—P3—C16—C17 | 0.7 (4) | O29—C25—C26A—C27A | −119 (13) |
Au2—P3—C16—C17 | −120.8 (4) | O29A—C25—C26A—C27A | 19 (4) |
C10—P3—C16—C21 | −74.0 (4) | C24—C25—C26A—C27A | −168 (3) |
C4—P3—C16—C21 | 174.3 (4) | C26—C25—O29A—C28A | 130 (4) |
Au2—P3—C16—C21 | 52.8 (4) | O29—C25—O29A—C28A | 4.6 (16) |
C21—C16—C17—C18 | −1.7 (7) | C26A—C25—O29A—C28A | −6 (2) |
P3—C16—C17—C18 | 172.1 (4) | C24—C25—O29A—C28A | −179.3 (9) |
C16—C17—C18—C19 | 0.2 (8) | C27A—C28A—O29A—C25 | −3.5 (18) |
C17—C18—C19—C20 | 1.2 (8) |
Experimental details
Crystal data | |
Chemical formula | [AuCl(C24H20NOP)] |
Mr | 601.80 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 173 |
a, b, c (Å) | 13.4559 (4), 10.3917 (2), 17.2641 (4) |
β (°) | 111.751 (1) |
V (Å3) | 2242.16 (9) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 6.77 |
Crystal size (mm) | 0.16 × 0.11 × 0.02 |
Data collection | |
Diffractometer | Bruker APEXII 4K CCD |
Absorption correction | Multi-scan (SADABS; Bruker, 2007) |
Tmin, Tmax | 0.411, 0.877 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 74340, 5536, 4175 |
Rint | 0.100 |
(sin θ/λ)max (Å−1) | 0.667 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.039, 0.100, 1.07 |
No. of reflections | 5536 |
No. of parameters | 299 |
No. of restraints | 240 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 2.27, −1.52 |
Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SAINT and XPREP (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), DIAMOND (Brandenburg & Putz, 2005), WinGX (Farrugia, 2012).
There is a growing interest in the co-ordination chemistry of ligands containing both hard (N donor) and soft (P donor) Lewis bases. Such ligands have the potential to bind to soft metal centers such as those of the platinum group metals strongly via phosphorus and weakly via nitrogen, which allows for the displacement of the chelating N-moiety. This is very desirable in homogenous catalytic reactions and the catalytic application of P—N based ligands is being thoroughly investigated by our group.
Among the 'hard' donor type atoms, the co-ordination chemistry of gold(I) shows a distinct paucity in the literature. In this scenario the potentially bidentate ligand is chelated to the metal through only the phosphorus atom (Fig. 1). The gold complex showed a closely linear P— Au—Cl system (bond angle of 176.49°). Another important geometrical parameter includes the C22—N23 = 1.254 (6) Å which is consistent with C=N double bonding. The Au—P bond distance of 2.2321 (13) Å agrees with that reported by Williams et al..