supplementary materials


zq2145 scheme

Acta Cryst. (2012). E68, m49    [ doi:10.1107/S1600536811052536 ]

Chlorido{N-[(E)-2-(diphenylphosphanyl)benzylidene]-2-(thiophen-2-yl)ethanamine-[kappa]P}gold(I)

H. Chiririwa and A. Muller

Abstract top

The title compound, [AuCl(C25H22NPS)], crystallizes with two independent molecules in the asymmetric unit in which the thiophene fragments are disordered over two sets of sites with 0.537 (10):0.463 (10) and 0.701 (9):0.299 (9) occupancy ratios. In both cases, the thiophene ring is rotated by approximately 180° for the second component. Important geometrical parameters include Au-P = 2.235 (2) and 2.237 (2) Å, Au-Cl = 2.286 (2) and 2.292 (2) Å, and P-Au-Cl = 177.39 (8) and 172.63 (7)°. Weak intermolecular C-H...Cl interactions are observed in the crystal structure.

Comment top

There is a growing interest in the coordination chemistry of iminophosphine ligands containing both hard (N donor) and soft (P donor) Lewis acids. Studies of gold(I) complexes have been related to anti-arthritic (Shaw, 1999), anti-tumor (Barnard et al., 2004) and antimicrobial physiological activities (Nomiya et al., 2003).

The asymmetric unit consists of two crystallographically independent molecules of the title compound, each having distinct features such as P1—Au1—Cl1 = 177.38 (9) and P2—Au2—Cl2 = 172.62 (8)°, respectively (Fig. 1). Bond lengths in the metal coordination environment are comparable and listed in the supplementary material for comparison. The thiophene fragments of each unit also show different packing behavior and had to be treated differently with independent disorder refinements [0.463 (10):0.537 (10) and 0.299 (9):0.701 (9) occupancy ratios]. In both cases the thiophene ring rotated approximately 180° for the second component. Conformational differences between the two independent molecules are highlighted in Figure 2 using Mercury (Macrae et al., 2006; Weng et al., 2008a; Weng et al., 2008b), with the root mean squared deviation (RMSD) calculated as 0.3274 Å. Weak intermolecular C—H···Cl interactions are observed in the crystal structure (Table 2).

Related literature top

For general background to the title compound, see: Shaw (1999); Barnard et al. (2004); Nomiya et al. (2003). For details on the conformational fit of the two molecules using Mercury, see: Macrae et al. (2006); Weng et al. (2008a,b).

Experimental top

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-thiophen-2-ylethanamine in CH2Cl2 (10 ml), and stirred at room temperature for 2 hrs. The solvent was reduced and the complex precipitated out on addition of hexane, filtered off, washed with Et2O (2 × 5 ml) and dried under vacuum for 4 hrs affording a white precipitate in 55% yield. Crystals suitable for X-ray structure determination were obtained by recrystallization from a CH2Cl2-hexane mixture at room temperature.

Refinement top

All H atoms were positioned in geometrically idealized positions with C—H = 0.99 Å and 0.95 Å for methylene and aromatic H atoms, respectively. All H atoms were allowed to ride on their parent atoms with Uiso(H) = 1.2Ueq(C). Disorder refinement models for two sites were applied to the thiophenes of each independent molecule in the asymmetric unit (hereafter referred to as molecule 1 and 2 for the unit containing Au1 and Au2, respectively). For the first molecule the disorder was more severe and C20/21 attached to the thiophene also had to be split. Geometrical (FLAT) restraints were applied to keep the rings C22A/B—C23A/B—C24A/B—C25A/B—S1A/B and C47A/B—C48A/B—C49A/B—C50A/B—S2A/B planar. Bond distance (DFIX) and 1,3 distance similarity restraints (SADI) were applied to obtain reasonable geometries. Ellipsoid displacement (SIMU and DELU) restraints were also applied to the disordered moieties. Free variables were connected to each disordered component to add to unity, respectively. Occupation parameters of the disordered atoms refined 0.537 (10) and 0.701 (9) for the major components of molecule 1 and 2, respectively. All the above restraints were applied with the default standard deviations for molecule 1. In the case of molecule 2 ellipsoid displacement restraints had to be adjusted to 0.02 and 0.005 for SIMU and DELU, respectively. Several reflections were omitted (as suggested by the checkCIF procedure) during refinement and can be found from the attached instruction file. The highest residual electron density of 1.63 e.Å-3 is 0.92 Å from Au2, representing no physical meaning.

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT and XPREP (Bruker, 2007); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg & Putz, 2005); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top
[Figure 1] Fig. 1. View of the asymmetric unit of the title compound. Displacement ellipsoids are drawn at the 30% probability level. For clarity: a) hydrogen atoms are omitted, b) bonds in part B of the disordered parts are indicated with dotted lines.
[Figure 2] Fig. 2. Conformational similarity of the two independent molecules in the asymmetric unit. Hydrogen atoms and the minor components of each disorder have been omitted for clarity.
Chlorido{N-[(E)-2-(diphenylphosphanyl)benzylidene]- 2-(thiophen-2-yl)ethanamine-κP}gold(I) top
Crystal data top
[AuCl(C25H22NPS)]F(000) = 2448
Mr = 631.88Dx = 1.828 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 12327 reflections
a = 11.866 (2) Åθ = 1.8–29.1°
b = 10.625 (2) ŵ = 6.70 mm1
c = 37.811 (7) ÅT = 173 K
β = 105.63 (3)°Plate, yellow
V = 4590.8 (16) Å30.14 × 0.13 × 0.06 mm
Z = 8
Data collection top
Bruker APEX DUO 4K CCD
diffractometer
11023 independent reflections
Graphite monochromator7856 reflections with I > 2σ(I)
Detector resolution: 8.4 pixels mm-1Rint = 0.126
ω scansθmax = 28°, θmin = 1.1°
Absorption correction: multi-scan
(SADABS; Bruker, 2007)
h = 1515
Tmin = 0.454, Tmax = 0.689k = 1414
107056 measured reflectionsl = 4949
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)] = 0.050Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.109H-atom parameters constrained
S = 1.12 w = 1/[σ2(Fo2) + (0.0302P)2 + 27.231P]
where P = (Fo2 + 2Fc2)/3
11023 reflections(Δ/σ)max = 0.003
642 parametersΔρmax = 1.63 e Å3
238 restraintsΔρmin = 1.24 e Å3
Crystal data top
[AuCl(C25H22NPS)]V = 4590.8 (16) Å3
Mr = 631.88Z = 8
Monoclinic, P21/cMo Kα radiation
a = 11.866 (2) ŵ = 6.70 mm1
b = 10.625 (2) ÅT = 173 K
c = 37.811 (7) Å0.14 × 0.13 × 0.06 mm
β = 105.63 (3)°
Data collection top
Bruker APEX DUO 4K CCD
diffractometer
11023 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2007)
7856 reflections with I > 2σ(I)
Tmin = 0.454, Tmax = 0.689Rint = 0.126
107056 measured reflectionsθmax = 28°
Refinement top
R[F2 > 2σ(F2)] = 0.050 w = 1/[σ2(Fo2) + (0.0302P)2 + 27.231P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.109Δρmax = 1.63 e Å3
S = 1.12Δρmin = 1.24 e Å3
11023 reflectionsAbsolute structure: ?
642 parametersFlack parameter: ?
238 restraintsRogers parameter: ?
H-atom parameters constrained
Special details top

Experimental. The intensity data was collected on a Bruker Apex DUO 4 K CCD diffractometer using an exposure time of 20 s/frame. A total of 1315 frames were collected with a frame width of 0.5° covering up to θ = 28.0° with 99.8% completeness accomplished.

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
Au10.23553 (3)0.21978 (3)1.006902 (8)0.03632 (9)
Cl10.23618 (19)0.1881 (2)1.06676 (5)0.0505 (5)
N10.0965 (7)0.0238 (8)0.9537 (2)0.056 (2)
P10.23365 (16)0.2413 (2)0.94794 (5)0.0337 (4)
C10.3179 (6)0.3787 (7)0.9410 (2)0.0326 (17)
C20.3387 (7)0.4763 (8)0.9659 (2)0.047 (2)
H20.30740.47280.98650.056*
C30.4050 (8)0.5803 (8)0.9612 (3)0.053 (2)
H30.4180.64720.97850.063*
C40.4507 (8)0.5860 (8)0.9322 (3)0.053 (2)
H40.49720.65610.92930.063*
C50.4292 (7)0.4879 (8)0.9064 (3)0.049 (2)
H50.45960.49270.88560.059*
C60.3654 (7)0.3865 (8)0.9108 (2)0.0411 (19)
H60.35260.320.89340.049*
C70.3049 (6)0.1130 (7)0.9301 (2)0.0360 (18)
C80.4113 (7)0.0707 (8)0.9517 (2)0.045 (2)
H80.4440.1060.97530.053*
C90.4705 (8)0.0243 (9)0.9385 (3)0.054 (2)
H90.54420.05310.9530.065*
C100.4221 (9)0.0764 (9)0.9044 (3)0.056 (2)
H100.46210.14180.89560.067*
C110.3173 (9)0.0345 (9)0.8833 (3)0.056 (2)
H110.28330.07120.85990.067*
C120.2605 (7)0.0620 (8)0.8960 (2)0.043 (2)
H120.1890.09340.88080.052*
C130.0879 (6)0.2660 (8)0.9165 (2)0.0374 (18)
C140.0683 (7)0.3772 (9)0.8960 (2)0.049 (2)
H140.13160.43340.89730.059*
C150.0429 (7)0.4076 (10)0.8735 (2)0.056 (2)
H150.05370.48270.85940.067*
C160.1353 (8)0.3302 (10)0.8718 (3)0.057 (3)
H160.21080.35140.85680.069*
C170.1189 (7)0.2206 (10)0.8921 (3)0.054 (2)
H170.18370.16650.89070.065*
C180.0078 (6)0.1867 (8)0.9149 (2)0.0396 (19)
C190.0009 (8)0.0668 (10)0.9347 (3)0.055 (2)
H190.06850.01980.9330.066*
C20A0.093 (2)0.085 (2)0.9774 (9)0.068 (9)0.537 (10)
H20A0.07720.05571.00050.081*0.537 (10)
H20B0.02840.14180.96490.081*0.537 (10)
C21A0.2022 (14)0.1538 (18)0.9860 (6)0.064 (5)0.537 (10)
H21A0.26720.09590.99740.077*0.537 (10)
H21B0.21590.18680.9630.077*0.537 (10)
C22A0.202 (2)0.261 (3)1.0117 (9)0.082 (8)0.537 (10)
C23A0.111 (3)0.343 (3)1.0118 (9)0.086 (9)0.537 (10)
H23A0.03590.33190.99530.103*0.537 (10)
C24A0.134 (2)0.444 (3)1.0368 (7)0.060 (6)0.537 (10)
H24A0.07990.50521.04060.072*0.537 (10)
C25A0.251 (2)0.434 (2)1.0547 (7)0.056 (5)0.537 (10)
H25A0.29140.49651.07130.067*0.537 (10)
S1A0.3179 (6)0.3043 (8)1.0450 (2)0.065 (2)0.537 (10)
C20B0.105 (3)0.108 (2)0.9668 (9)0.079 (12)0.463 (10)
H20C0.0270.13850.96740.095*0.463 (10)
H20D0.1330.1620.94940.095*0.463 (10)
C21B0.185 (2)0.1203 (16)1.0029 (5)0.077 (7)0.463 (10)
H21C0.15580.06741.02010.093*0.463 (10)
H21D0.26210.08741.00220.093*0.463 (10)
C22B0.199 (3)0.251 (2)1.0171 (10)0.083 (9)0.463 (10)
C23B0.289 (3)0.300 (3)1.0450 (9)0.093 (13)0.463 (10)
H23B0.35790.25141.05480.112*0.463 (10)
C24B0.279 (3)0.419 (3)1.0585 (11)0.083 (10)0.463 (10)
H24B0.33570.46251.0770.1*0.463 (10)
C25B0.170 (2)0.462 (3)1.0394 (9)0.069 (8)0.463 (10)
H25B0.13890.53971.04470.083*0.463 (10)
S1B0.0946 (10)0.3640 (12)1.0058 (4)0.101 (5)0.463 (10)
Au20.28143 (2)0.48017 (3)0.777307 (8)0.03068 (8)
Cl20.21265 (17)0.32072 (19)0.80665 (6)0.0454 (5)
N20.1363 (5)0.6132 (6)0.70443 (17)0.0362 (15)
P20.35877 (15)0.64601 (18)0.75586 (5)0.0289 (4)
C260.5016 (6)0.6658 (7)0.7892 (2)0.0299 (16)
C270.5040 (6)0.6648 (7)0.8265 (2)0.0379 (18)
H270.43270.66210.83340.046*
C280.6086 (7)0.6677 (8)0.8532 (2)0.044 (2)
H280.60890.67050.87830.053*
C290.7130 (7)0.6664 (8)0.8439 (2)0.045 (2)
H290.78510.66630.86250.054*
C300.7121 (7)0.6652 (8)0.8075 (2)0.046 (2)
H300.78380.66360.80090.056*
C310.6057 (6)0.6661 (7)0.7802 (2)0.0356 (18)
H310.60580.6670.75510.043*
C320.3900 (6)0.6424 (7)0.7114 (2)0.0300 (16)
C330.3777 (6)0.5337 (8)0.6909 (2)0.0378 (18)
H330.35270.45830.69990.045*
C340.4022 (7)0.5348 (9)0.6566 (2)0.045 (2)
H340.39140.46090.64190.054*
C350.4417 (7)0.6435 (9)0.6446 (2)0.045 (2)
H350.45920.6440.62150.054*
C360.4565 (7)0.7507 (9)0.6650 (2)0.046 (2)
H360.48490.82480.65630.056*
C370.4300 (6)0.7518 (8)0.6987 (2)0.0366 (18)
H370.43910.82680.71290.044*
C380.2807 (6)0.7954 (7)0.75625 (19)0.0303 (16)
C390.3250 (7)0.8907 (6)0.77927 (19)0.0331 (17)
H390.39990.8760.79570.04*
C400.2783 (7)1.0025 (7)0.7822 (2)0.0392 (19)
H400.31961.0650.79860.047*
C410.1638 (7)1.0238 (8)0.7596 (2)0.044 (2)
H410.12431.10070.76080.052*
C420.1113 (7)0.9300 (7)0.7357 (2)0.0401 (19)
H420.03520.94430.720.048*
C430.1660 (6)0.8137 (7)0.7336 (2)0.0346 (17)
C440.0976 (6)0.7203 (8)0.7085 (2)0.0397 (19)
H440.02050.74160.69480.048*
C450.0589 (8)0.5299 (8)0.6788 (2)0.050 (2)
H45A0.08290.52580.65570.06*
H45B0.02210.56280.6730.06*
C460.0628 (8)0.3992 (9)0.6952 (3)0.057 (2)
H46A0.14420.36750.7010.069*
H46B0.04040.40480.71860.069*
C470.0150 (7)0.3080 (8)0.6709 (2)0.0476 (18)
C48A0.093 (3)0.224 (3)0.6782 (7)0.054 (6)0.299 (9)
H48A0.10080.21630.70250.065*0.299 (9)
C49A0.161 (4)0.150 (4)0.6508 (9)0.059 (8)0.299 (9)
H49A0.21820.09080.65320.071*0.299 (9)
C50A0.129 (4)0.179 (4)0.6195 (9)0.060 (7)0.299 (9)
H50A0.15980.13740.59660.072*0.299 (9)
S2A0.0301 (12)0.2967 (13)0.6264 (3)0.054 (3)0.299 (9)
C48B0.0478 (19)0.293 (2)0.6343 (4)0.062 (5)0.701 (9)
H48B0.01510.34590.61940.075*0.701 (9)
C49B0.128 (2)0.2032 (18)0.6183 (6)0.073 (5)0.701 (9)
H49B0.15560.18630.59270.088*0.701 (9)
C50B0.160 (2)0.142 (2)0.6457 (4)0.058 (4)0.701 (9)
H50B0.21360.07380.64170.07*0.701 (9)
S2B0.0933 (4)0.2027 (4)0.68793 (11)0.0512 (13)0.701 (9)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Au10.03364 (16)0.0476 (2)0.02662 (15)0.00584 (13)0.00630 (12)0.00317 (13)
Cl10.0577 (13)0.0663 (15)0.0277 (10)0.0160 (11)0.0119 (9)0.0042 (10)
N10.048 (4)0.069 (5)0.052 (5)0.013 (4)0.016 (4)0.007 (4)
P10.0283 (9)0.0448 (12)0.0264 (10)0.0059 (8)0.0049 (8)0.0024 (9)
C10.027 (4)0.031 (4)0.038 (4)0.004 (3)0.006 (3)0.003 (3)
C20.051 (5)0.053 (5)0.037 (5)0.010 (4)0.013 (4)0.006 (4)
C30.063 (6)0.038 (5)0.059 (6)0.011 (4)0.021 (5)0.007 (4)
C40.047 (5)0.039 (5)0.071 (7)0.006 (4)0.014 (5)0.009 (5)
C50.050 (5)0.046 (5)0.054 (6)0.004 (4)0.019 (4)0.012 (4)
C60.040 (4)0.040 (5)0.044 (5)0.001 (4)0.012 (4)0.001 (4)
C70.029 (4)0.040 (5)0.041 (5)0.008 (3)0.013 (3)0.002 (4)
C80.044 (5)0.051 (5)0.038 (5)0.007 (4)0.011 (4)0.007 (4)
C90.050 (5)0.056 (6)0.059 (6)0.018 (5)0.020 (5)0.022 (5)
C100.078 (7)0.039 (5)0.065 (7)0.001 (5)0.043 (6)0.006 (5)
C110.069 (6)0.053 (6)0.051 (6)0.014 (5)0.024 (5)0.015 (5)
C120.038 (4)0.053 (5)0.037 (5)0.001 (4)0.009 (4)0.006 (4)
C130.029 (4)0.053 (5)0.028 (4)0.001 (4)0.005 (3)0.008 (4)
C140.037 (4)0.065 (6)0.042 (5)0.003 (4)0.004 (4)0.009 (4)
C150.043 (5)0.070 (7)0.049 (6)0.009 (5)0.003 (4)0.007 (5)
C160.034 (5)0.074 (7)0.058 (6)0.006 (5)0.004 (4)0.006 (5)
C170.030 (4)0.073 (7)0.056 (6)0.010 (4)0.008 (4)0.029 (5)
C180.034 (4)0.048 (5)0.037 (5)0.002 (4)0.010 (3)0.013 (4)
C190.044 (5)0.068 (7)0.055 (6)0.023 (5)0.017 (4)0.014 (5)
C20A0.056 (12)0.083 (17)0.070 (19)0.007 (10)0.028 (12)0.035 (13)
C21A0.051 (9)0.066 (12)0.059 (12)0.008 (8)0.012 (9)0.002 (8)
C22A0.066 (12)0.083 (15)0.081 (16)0.001 (9)0.006 (11)0.026 (12)
C23A0.050 (11)0.09 (2)0.11 (2)0.015 (11)0.008 (12)0.035 (14)
C24A0.056 (12)0.073 (13)0.057 (13)0.010 (10)0.024 (10)0.004 (9)
C25A0.053 (11)0.080 (12)0.042 (11)0.022 (8)0.026 (8)0.008 (9)
S1A0.049 (3)0.090 (5)0.054 (4)0.007 (3)0.013 (2)0.002 (3)
C20B0.09 (2)0.084 (18)0.057 (17)0.052 (16)0.014 (14)0.012 (13)
C21B0.124 (19)0.046 (9)0.055 (13)0.012 (11)0.013 (13)0.030 (9)
C22B0.094 (17)0.054 (11)0.081 (17)0.030 (11)0.013 (13)0.011 (11)
C23B0.072 (18)0.076 (18)0.12 (2)0.010 (13)0.002 (15)0.000 (15)
C24B0.066 (15)0.095 (18)0.09 (2)0.006 (14)0.018 (11)0.015 (15)
C25B0.051 (15)0.065 (14)0.098 (17)0.012 (11)0.032 (12)0.010 (12)
S1B0.063 (6)0.082 (6)0.137 (9)0.025 (5)0.006 (5)0.038 (6)
Au20.02441 (13)0.02998 (15)0.03575 (16)0.00214 (12)0.00485 (11)0.00045 (13)
Cl20.0407 (11)0.0350 (11)0.0600 (13)0.0067 (8)0.0129 (9)0.0058 (9)
N20.031 (3)0.036 (4)0.038 (4)0.002 (3)0.004 (3)0.005 (3)
P20.0231 (9)0.0310 (11)0.0320 (10)0.0026 (7)0.0064 (7)0.0006 (8)
C260.026 (3)0.025 (4)0.036 (4)0.003 (3)0.003 (3)0.003 (3)
C270.033 (4)0.040 (5)0.040 (5)0.007 (3)0.009 (3)0.000 (4)
C280.045 (5)0.039 (5)0.040 (5)0.008 (4)0.001 (4)0.001 (4)
C290.032 (4)0.049 (5)0.045 (5)0.007 (4)0.005 (4)0.008 (4)
C300.032 (4)0.054 (6)0.050 (5)0.002 (4)0.007 (4)0.008 (4)
C310.031 (4)0.039 (5)0.035 (4)0.001 (3)0.008 (3)0.007 (3)
C320.022 (3)0.031 (4)0.034 (4)0.003 (3)0.004 (3)0.003 (3)
C330.030 (4)0.039 (5)0.041 (5)0.007 (3)0.003 (3)0.002 (4)
C340.041 (4)0.055 (6)0.039 (5)0.017 (4)0.007 (4)0.011 (4)
C350.038 (4)0.058 (6)0.042 (5)0.014 (4)0.014 (4)0.005 (4)
C360.042 (5)0.057 (6)0.042 (5)0.004 (4)0.014 (4)0.013 (4)
C370.034 (4)0.040 (5)0.036 (4)0.004 (3)0.008 (3)0.001 (3)
C380.030 (4)0.034 (4)0.028 (4)0.000 (3)0.012 (3)0.000 (3)
C390.073 (5)0.008 (3)0.021 (4)0.009 (3)0.018 (4)0.001 (3)
C400.043 (4)0.036 (5)0.039 (5)0.008 (4)0.013 (4)0.003 (4)
C410.044 (5)0.045 (5)0.048 (5)0.007 (4)0.024 (4)0.006 (4)
C420.037 (4)0.033 (4)0.048 (5)0.006 (3)0.006 (4)0.002 (4)
C430.032 (4)0.030 (4)0.042 (5)0.004 (3)0.009 (3)0.003 (3)
C440.024 (4)0.043 (5)0.046 (5)0.001 (3)0.003 (3)0.011 (4)
C450.050 (5)0.042 (5)0.046 (5)0.006 (4)0.008 (4)0.007 (4)
C460.047 (5)0.057 (6)0.065 (6)0.009 (4)0.009 (5)0.005 (5)
C470.041 (4)0.040 (4)0.058 (4)0.001 (3)0.007 (3)0.003 (3)
C48A0.048 (13)0.040 (13)0.072 (9)0.001 (9)0.014 (10)0.000 (10)
C49A0.056 (15)0.032 (15)0.081 (14)0.004 (10)0.003 (11)0.007 (12)
C50A0.071 (14)0.028 (13)0.068 (10)0.004 (9)0.004 (11)0.001 (10)
S2A0.059 (6)0.041 (6)0.057 (4)0.007 (4)0.005 (4)0.003 (4)
C48B0.084 (11)0.042 (9)0.057 (5)0.014 (7)0.011 (7)0.003 (7)
C49B0.109 (11)0.041 (10)0.056 (4)0.015 (8)0.001 (7)0.006 (6)
C50B0.061 (10)0.043 (9)0.072 (6)0.012 (6)0.021 (7)0.021 (7)
S2B0.052 (2)0.046 (2)0.061 (2)0.0130 (17)0.0245 (18)0.0151 (18)
Geometric parameters (Å, º) top
Au1—P12.235 (2)C24B—H24B0.95
Au1—Cl12.286 (2)C25B—S1B1.695 (17)
N1—C191.254 (11)C25B—H25B0.95
N1—C20A1.471 (18)Au2—P22.237 (2)
N1—C20B1.484 (19)Au2—Cl22.292 (2)
P1—C71.826 (8)N2—C441.252 (10)
P1—C11.828 (8)N2—C451.444 (10)
P1—C131.835 (7)P2—C321.818 (8)
C1—C21.377 (11)P2—C261.832 (7)
C1—C61.403 (11)P2—C381.840 (7)
C2—C31.395 (12)C26—C311.368 (10)
C2—H20.95C26—C271.403 (10)
C3—C41.350 (12)C27—C281.371 (10)
C3—H30.95C27—H270.95
C4—C51.404 (13)C28—C291.375 (12)
C4—H40.95C28—H280.95
C5—C61.353 (11)C29—C301.371 (12)
C5—H50.95C29—H290.95
C6—H60.95C30—C311.400 (10)
C7—C121.366 (11)C30—H300.95
C7—C81.380 (11)C31—H310.95
C8—C91.397 (12)C32—C331.376 (10)
C8—H80.95C32—C371.389 (10)
C9—C101.377 (13)C33—C341.401 (11)
C9—H90.95C33—H330.95
C10—C111.359 (13)C34—C351.370 (12)
C10—H100.95C34—H340.95
C11—C121.383 (12)C35—C361.361 (12)
C11—H110.95C35—H350.95
C12—H120.95C36—C371.392 (11)
C13—C141.398 (12)C36—H360.95
C13—C181.403 (11)C37—H370.95
C14—C151.400 (11)C38—C391.346 (10)
C14—H140.95C38—C431.413 (10)
C15—C161.359 (13)C39—C401.327 (10)
C15—H150.95C39—H390.95
C16—C171.379 (13)C40—C411.415 (11)
C16—H160.95C40—H400.95
C17—C181.413 (11)C41—C421.376 (11)
C17—H170.95C41—H410.95
C18—C191.466 (13)C42—C431.407 (10)
C19—H190.95C42—H420.95
C20A—C21A1.45 (2)C43—C441.458 (11)
C20A—H20A0.99C44—H440.95
C20A—H20B0.99C45—C461.516 (12)
C21A—C22A1.50 (2)C45—H45A0.99
C21A—H21A0.99C45—H45B0.99
C21A—H21B0.99C46—C471.476 (11)
C22A—C23A1.383 (16)C46—H46A0.99
C22A—S1A1.661 (14)C46—H46B0.99
C23A—C24A1.405 (17)C47—C48B1.341 (15)
C23A—H23A0.95C47—C48A1.371 (18)
C24A—C25A1.378 (15)C47—S2A1.646 (12)
C24A—H24A0.95C47—S2B1.689 (9)
C25A—S1A1.680 (16)C48A—C49A1.370 (13)
C25A—H25A0.95C48A—H48A0.95
C20B—C21B1.44 (2)C49A—C50A1.369 (13)
C20B—H20C0.99C49A—H49A0.95
C20B—H20D0.99C50A—S2A1.692 (17)
C21B—C22B1.49 (2)C50A—H50A0.95
C21B—H21C0.99C48B—C49B1.369 (12)
C21B—H21D0.99C48B—H48B0.95
C22B—C23B1.382 (16)C49B—C50B1.362 (11)
C22B—S1B1.695 (16)C49B—H49B0.95
C23B—C24B1.383 (17)C50B—S2B1.706 (12)
C23B—H23B0.95C50B—H50B0.95
C24B—C25B1.381 (17)
P1—Au1—Cl1177.39 (8)C23B—C24B—H24B127.2
C19—N1—C20A117.8 (12)C24B—C25B—S1B115 (3)
C19—N1—C20B120.6 (13)C24B—C25B—H25B122.5
C7—P1—C1102.6 (3)S1B—C25B—H25B122.5
C7—P1—C13108.4 (4)C25B—S1B—C22B92.4 (13)
C1—P1—C13104.4 (4)P2—Au2—Cl2172.63 (7)
C7—P1—Au1114.2 (3)C44—N2—C45116.9 (7)
C1—P1—Au1111.5 (3)C32—P2—C26104.9 (3)
C13—P1—Au1114.6 (3)C32—P2—C38104.7 (3)
C2—C1—C6118.3 (7)C26—P2—C38105.7 (3)
C2—C1—P1120.5 (6)C32—P2—Au2121.6 (3)
C6—C1—P1121.2 (6)C26—P2—Au2103.6 (2)
C1—C2—C3120.8 (8)C38—P2—Au2114.8 (2)
C1—C2—H2119.6C31—C26—C27118.5 (7)
C3—C2—H2119.6C31—C26—P2123.9 (6)
C4—C3—C2120.2 (9)C27—C26—P2117.1 (5)
C4—C3—H3119.9C28—C27—C26120.5 (7)
C2—C3—H3119.9C28—C27—H27119.8
C3—C4—C5119.6 (8)C26—C27—H27119.8
C3—C4—H4120.2C27—C28—C29120.8 (8)
C5—C4—H4120.2C27—C28—H28119.6
C6—C5—C4120.5 (8)C29—C28—H28119.6
C6—C5—H5119.7C30—C29—C28119.4 (7)
C4—C5—H5119.7C30—C29—H29120.3
C5—C6—C1120.6 (8)C28—C29—H29120.3
C5—C6—H6119.7C29—C30—C31120.2 (8)
C1—C6—H6119.7C29—C30—H30119.9
C12—C7—C8119.1 (8)C31—C30—H30119.9
C12—C7—P1123.1 (6)C26—C31—C30120.6 (7)
C8—C7—P1117.8 (6)C26—C31—H31119.7
C7—C8—C9119.5 (8)C30—C31—H31119.7
C7—C8—H8120.2C33—C32—C37120.1 (7)
C9—C8—H8120.2C33—C32—P2121.5 (6)
C10—C9—C8120.1 (8)C37—C32—P2118.4 (6)
C10—C9—H9120C32—C33—C34119.8 (8)
C8—C9—H9120C32—C33—H33120.1
C11—C10—C9120.2 (9)C34—C33—H33120.1
C11—C10—H10119.9C35—C34—C33119.3 (8)
C9—C10—H10119.9C35—C34—H34120.4
C10—C11—C12119.5 (9)C33—C34—H34120.4
C10—C11—H11120.2C36—C35—C34121.3 (8)
C12—C11—H11120.2C36—C35—H35119.3
C7—C12—C11121.5 (8)C34—C35—H35119.3
C7—C12—H12119.2C35—C36—C37120.0 (8)
C11—C12—H12119.2C35—C36—H36120
C14—C13—C18118.3 (7)C37—C36—H36120
C14—C13—P1117.9 (6)C32—C37—C36119.4 (8)
C18—C13—P1123.5 (6)C32—C37—H37120.3
C13—C14—C15121.3 (9)C36—C37—H37120.3
C13—C14—H14119.3C39—C38—C43115.7 (7)
C15—C14—H14119.3C39—C38—P2123.0 (6)
C16—C15—C14120.3 (9)C43—C38—P2121.3 (6)
C16—C15—H15119.8C40—C39—C38128.8 (8)
C14—C15—H15119.8C40—C39—H39115.6
C15—C16—C17119.6 (8)C38—C39—H39115.6
C15—C16—H16120.2C39—C40—C41116.6 (8)
C17—C16—H16120.2C39—C40—H40121.7
C16—C17—C18121.6 (8)C41—C40—H40121.7
C16—C17—H17119.2C42—C41—C40118.1 (8)
C18—C17—H17119.2C42—C41—H41120.9
C13—C18—C17118.8 (8)C40—C41—H41120.9
C13—C18—C19123.8 (7)C41—C42—C43122.5 (7)
C17—C18—C19117.3 (8)C41—C42—H42118.7
N1—C19—C18122.5 (8)C43—C42—H42118.7
N1—C19—H19118.7C42—C43—C38118.1 (7)
C18—C19—H19118.7C42—C43—C44116.7 (7)
C21A—C20A—N1111.3 (18)C38—C43—C44125.2 (7)
C21A—C20A—H20A109.4N2—C44—C43122.7 (7)
N1—C20A—H20A109.4N2—C44—H44118.6
C21A—C20A—H20B109.4C43—C44—H44118.6
N1—C20A—H20B109.4N2—C45—C46110.1 (7)
H20A—C20A—H20B108N2—C45—H45A109.6
C20A—C21A—C22A111.7 (17)C46—C45—H45A109.6
C20A—C21A—H21A109.3N2—C45—H45B109.6
C22A—C21A—H21A109.3C46—C45—H45B109.6
C20A—C21A—H21B109.3H45A—C45—H45B108.2
C22A—C21A—H21B109.3C47—C46—C45113.7 (8)
H21A—C21A—H21B107.9C47—C46—H46A108.8
C23A—C22A—C21A128.2 (17)C45—C46—H46A108.8
C23A—C22A—S1A108.2 (15)C47—C46—H46B108.8
C21A—C22A—S1A123.6 (15)C45—C46—H46B108.8
C22A—C23A—C24A118 (3)H46A—C46—H46B107.7
C22A—C23A—H23A120.9C48B—C47—C48A96.2 (18)
C24A—C23A—H23A120.9C48B—C47—C46132.7 (11)
C25A—C24A—C23A105 (3)C48A—C47—C46130.3 (13)
C25A—C24A—H24A127.6C48A—C47—S2A105.4 (12)
C23A—C24A—H24A127.6C46—C47—S2A124.2 (7)
C24A—C25A—S1A115 (2)C48B—C47—S2B106.2 (10)
C24A—C25A—H25A122.3C46—C47—S2B120.9 (7)
S1A—C25A—H25A122.3S2A—C47—S2B114.9 (6)
C22A—S1A—C25A92.7 (11)C49A—C48A—C47121 (2)
C21B—C20B—N1111.7 (19)C49A—C48A—H48A119.7
C21B—C20B—H20C109.3C47—C48A—H48A119.7
N1—C20B—H20C109.3C50A—C49A—C48A107 (2)
C21B—C20B—H20D109.3C50A—C49A—H49A126.6
N1—C20B—H20D109.3C48A—C49A—H49A126.6
H20C—C20B—H20D107.9C49A—C50A—S2A112 (2)
C20B—C21B—C22B114.1 (16)C49A—C50A—H50A124.2
C20B—C21B—H21C108.7S2A—C50A—H50A124.2
C22B—C21B—H21C108.7C47—S2A—C50A95.3 (12)
C20B—C21B—H21D108.7C47—C48B—C49B120.9 (19)
C22B—C21B—H21D108.7C47—C48B—H48B119.6
H21C—C21B—H21D107.6C49B—C48B—H48B119.6
C23B—C22B—C21B128.1 (19)C50B—C49B—C48B107 (2)
C23B—C22B—S1B106.9 (14)C50B—C49B—H49B126.3
C21B—C22B—S1B124.4 (16)C48B—C49B—H49B126.3
C22B—C23B—C24B120 (3)C49B—C50B—S2B112.2 (15)
C22B—C23B—H23B120.1C49B—C50B—H50B123.9
C24B—C23B—H23B120.1S2B—C50B—H50B123.9
C25B—C24B—C23B106 (3)C47—S2B—C50B93.2 (8)
C25B—C24B—H24B127.2
C7—P1—C1—C2144.9 (6)Au2—P2—C26—C31123.7 (6)
C13—P1—C1—C2102.0 (7)C32—P2—C26—C27176.6 (6)
Au1—P1—C1—C222.3 (7)C38—P2—C26—C2773.0 (6)
C7—P1—C1—C633.5 (7)Au2—P2—C26—C2748.1 (6)
C13—P1—C1—C679.6 (7)C31—C26—C27—C281.8 (11)
Au1—P1—C1—C6156.2 (5)P2—C26—C27—C28174.1 (6)
C6—C1—C2—C30.1 (12)C26—C27—C28—C292.7 (12)
P1—C1—C2—C3178.6 (7)C27—C28—C29—C301.5 (13)
C1—C2—C3—C40.6 (14)C28—C29—C30—C310.5 (13)
C2—C3—C4—C51.3 (14)C27—C26—C31—C300.2 (11)
C3—C4—C5—C61.6 (13)P2—C26—C31—C30171.6 (6)
C4—C5—C6—C11.2 (12)C29—C30—C31—C261.3 (13)
C2—C1—C6—C50.4 (11)C26—P2—C32—C33110.4 (6)
P1—C1—C6—C5178.9 (6)C38—P2—C32—C33138.5 (6)
C1—P1—C7—C12100.5 (7)Au2—P2—C32—C336.3 (7)
C13—P1—C7—C129.5 (8)C26—P2—C32—C3767.9 (6)
Au1—P1—C7—C12138.7 (6)C38—P2—C32—C3743.1 (6)
C1—P1—C7—C876.3 (7)Au2—P2—C32—C37175.4 (4)
C13—P1—C7—C8173.7 (6)C37—C32—C33—C342.0 (10)
Au1—P1—C7—C844.5 (7)P2—C32—C33—C34179.7 (5)
C12—C7—C8—C90.9 (12)C32—C33—C34—C352.1 (11)
P1—C7—C8—C9177.8 (6)C33—C34—C35—C360.7 (12)
C7—C8—C9—C100.9 (13)C34—C35—C36—C370.8 (12)
C8—C9—C10—C110.8 (14)C33—C32—C37—C360.5 (11)
C9—C10—C11—C120.9 (14)P2—C32—C37—C36178.9 (6)
C8—C7—C12—C112.7 (13)C35—C36—C37—C320.9 (11)
P1—C7—C12—C11179.4 (7)C32—P2—C38—C39114.3 (6)
C10—C11—C12—C72.7 (14)C26—P2—C38—C393.8 (7)
C7—P1—C13—C14111.2 (7)Au2—P2—C38—C39109.7 (6)
C1—P1—C13—C142.4 (7)C32—P2—C38—C4369.7 (6)
Au1—P1—C13—C14119.9 (6)C26—P2—C38—C43179.7 (6)
C7—P1—C13—C1876.3 (7)Au2—P2—C38—C4366.3 (6)
C1—P1—C13—C18174.9 (6)C43—C38—C39—C404.2 (12)
Au1—P1—C13—C1852.7 (7)P2—C38—C39—C40179.6 (6)
C18—C13—C14—C152.0 (13)C38—C39—C40—C413.7 (12)
P1—C13—C14—C15175.0 (7)C39—C40—C41—C422.1 (11)
C13—C14—C15—C161.5 (14)C40—C41—C42—C431.5 (12)
C14—C15—C16—C170.7 (14)C41—C42—C43—C382.1 (12)
C15—C16—C17—C180.4 (14)C41—C42—C43—C44176.6 (8)
C14—C13—C18—C171.7 (11)C39—C38—C43—C423.1 (10)
P1—C13—C18—C17174.2 (6)P2—C38—C43—C42179.3 (6)
C14—C13—C18—C19179.2 (8)C39—C38—C43—C44175.5 (7)
P1—C13—C18—C198.3 (11)P2—C38—C43—C440.7 (11)
C16—C17—C18—C131.0 (12)C45—N2—C44—C43179.7 (7)
C16—C17—C18—C19178.6 (8)C42—C43—C44—N2179.6 (8)
C20A—N1—C19—C18169.5 (18)C38—C43—C44—N21.0 (13)
C20B—N1—C19—C18167 (2)C44—N2—C45—C46135.6 (8)
C13—C18—C19—N12.3 (14)N2—C45—C46—C47179.4 (7)
C17—C18—C19—N1175.2 (9)C45—C46—C47—C48B34.4 (18)
C19—N1—C20A—C21A157 (2)C45—C46—C47—C48A133 (2)
C20B—N1—C20A—C21A54 (4)C45—C46—C47—S2A42.5 (14)
N1—C20A—C21A—C22A177 (2)C45—C46—C47—S2B139.4 (8)
C20A—C21A—C22A—C23A40 (4)C48B—C47—C48A—C49A7 (2)
C20A—C21A—C22A—S1A143 (3)C46—C47—C48A—C49A177 (2)
C21A—C22A—C23A—C24A175 (4)S2A—C47—C48A—C49A1.7 (19)
S1A—C22A—C23A—C24A2.6 (18)S2B—C47—C48A—C49A150 (10)
C22A—C23A—C24A—C25A2.7 (18)C47—C48A—C49A—C50A1 (2)
C23A—C24A—C25A—S1A7 (2)C48A—C49A—C50A—S2A4 (3)
C23A—C22A—S1A—C25A5.5 (18)C48B—C47—S2A—C50A33 (8)
C21A—C22A—S1A—C25A172 (3)C48A—C47—S2A—C50A3 (2)
C24A—C25A—S1A—C22A8 (2)C46—C47—S2A—C50A179 (2)
C19—N1—C20B—C21B144 (2)S2B—C47—S2A—C50A2 (2)
C20A—N1—C20B—C21B56 (4)C49A—C50A—S2A—C474 (3)
N1—C20B—C21B—C22B179 (3)C48A—C47—C48B—C49B6 (3)
C20B—C21B—C22B—C23B161 (4)C46—C47—C48B—C49B176.3 (14)
C20B—C21B—C22B—S1B30 (5)S2A—C47—C48B—C49B145 (8)
C21B—C22B—C23B—C24B170 (5)S2B—C47—C48B—C49B1.8 (16)
S1B—C22B—C23B—C24B1.6 (18)C47—C48B—C49B—C50B0.2 (19)
C22B—C23B—C24B—C25B2 (2)C48B—C49B—C50B—S2B1.6 (19)
C23B—C24B—C25B—S1B4 (3)C48B—C47—S2B—C50B2.2 (14)
C24B—C25B—S1B—C22B5 (3)C48A—C47—S2B—C50B26 (10)
C23B—C22B—S1B—C25B3 (2)C46—C47—S2B—C50B177.5 (11)
C21B—C22B—S1B—C25B168 (4)S2A—C47—S2B—C50B4.2 (12)
C32—P2—C26—C314.8 (7)C49B—C50B—S2B—C472.3 (17)
C38—P2—C26—C31115.2 (7)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C28—H28···Cl1i0.952.813.454 (9)126
Symmetry code: (i) x+1, y+1, z+2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C28—H28···Cl1i0.952.813.454 (9)126
Symmetry code: (i) x+1, y+1, z+2.
Acknowledgements top

Financial assistance from the South African National Research Foundation (SA NRF), the Research Fund of the University of Johannesburg and SASOL is gratefully acknowledged.

references
References top

Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115–119.

Barnard, P. J., Baker, M. V., Berners-Price, S. J. & Day, D. A. (2004). J. Inorg. Biochem. 98, 1642–1647.

Brandenburg, K. & Putz, H. (2005). DIAMOND. Crystal Impact GbR, Bonn, Germany.

Bruker (2007). APEX2, XPREP, SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.

Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838.

Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453–457.

Nomiya, K., Yamamoto, S., Noguchi, R., Yokoyama, H., Kasuga, N. C., Ohyama, K. & Kato, C. (2003). J. Inorg. Biochem. 95, 208–220.

Shaw, C. F. III (1999). Chem. Rev. 99, 2589–2600.

Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.

Weng, Z. F., Motherwell, W. D. S., Allen, F. H. & Cole, J. M. (2008a). Acta Cryst. B64, 348–362.

Weng, Z. F., Motherwell, W. D. S. & Cole, J. M. (2008b). J. Appl. Cryst. 41, 955–957.