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The title compound, [Au(C7H7S)(C18H15P)], is conformationally chiral and crystallizes from benzene-hexane as individually enantio­pure crystals. This mononuclear compound has the AuI atom linearly bound to a triphenyl­phosphine P atom and to a phenyl C atom of a 2-(methyl­sulfanyl)phenyl group. The angle at the AuI atom is 175.9 (2)°. The linear ligand coordination about the AuI atom has geometric parameters inside the remarkably narrow range found for gold complexes bound by a phosphine ligand and by the ortho-C atom of a substituted phenyl group. This is the first example of gold(I) attached to a methyl­sulfanyl aromatic carbanion.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270109017831/fa3184sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270109017831/fa3184Isup2.hkl
Contains datablock I

CCDC reference: 746043

Comment top

Gold carbanion connections are strong, as revealed by structural (Schmidbaur, 1995) and theoretical energy studies (Dargel et al., 1999). However, establishing such bonds usually demands reactive carbon precursors (organolithium or Grignard reagents) (Fernandez et al., 2004) with some reduction of gold to Au0. This inconvenience has prompted the search for more efficient procedures to generate Au—C bonds. Gray (2009), using boronic acids ArB(OH)2 as carbon-delivering substrates, has shown these reagents to give good yields of the desired aromatic carbanion products with LAuBr (where L is a bulky PR3, N-heterocyclic carbene) and an assisting base. In this report, we describe a transmetallation from boron to gold using Ph3PAuCl instead of LAuBr. The reaction proceeds with an excellent yield to give the title substituted triphenylphosphine gold(I) compound, [(Ph)3PAuI(2-C6H4SCH3], (I), under very controllable conditions.

Efficient protocols for generating Au—C bonded products are in demand, since the optical properties found for such compounds (Fackler, 2002; Gray, 2007) may be applied in opto-electronic devices (LEDs, organic LEDs or photovoltaic cells; Wong & Guo, 2008). Optical properties such as luminescence are enhanced by the heavy gold centre (spin-orbit coupling) attached to a variety of organic molecules such as pyrene (Heng et al., 2007), phenyls, heteroaromatic rings (Wong et al., 2007) and alkynyls (Yam et al., 2003), in mononuclear (King et al., 1992) and in polynuclear complexes (Hong et al., 1994; Rios et al., 2008).

Compound (I) is the first example of gold(I) attached to a thiomethyl aromatic carbanion. Even though the ortho thio unit on the ring could bond to Au to produce a four-membered chelate ring, the long Au1···S1 distance of 3.246 (3) Å shows that this does not happen. Connectivity of S to Au of a neighbouring molecule is apparently hindered by the phenyl rings of the phosphine, which obviate any aurophilic interactions [Au···Au = 6.986 (4) Å]. The propeller organization of the phenyl rings on the phosphine lowers the symmetry of the molecule (with no improper rotations), making it chiral.

From what is expected to be a racemic mixture of the product, only one of the two conformational enantiomers is present in the crystal structure (Fig. 1), so the crystalline product is in all likelihood a racemic conglomerate. The chiral space group P212121 is that which is most frequently observed for enantiopure crystals, according to Jacques et al. (1981).

Each mononuclear AuI centre has a linear ligand coordination with geometric parameters inside the remarkably narrow range found in this family of compounds. There are 17 examples in the Cambridge Structural Database (CSD, version 5.30; Allen, 2002) of gold(I) linearly bonded to a phosphine and to the C atom of an ortho-substituted phenyl group, including one with an Au—C π bond. Fifteen of these report three-dimensional coordinates (Table 1). Their Au—P and Au—C distances are similar to those of the title compound and they also show angular interactions involving phenyl rings (C—H···π interactions). Fourteen are non-chiral and in fact crystallize in centrosymmetric space groups. There is one chiral compound, the dimer [(µ2-2,2'-bis(phenylene)methane)-(µ2-1,2-bis(diphenylphosphino)ethane)-digold(I)], which crystallizes in the space group P21. In spite of the presence of four phenyl rings in (I), there are no ππ stacking interactions, but there are angular interactions between C-bound H atoms and phenyl rings of neighbouring molecules. There is one C—H···π contact of note, from C21—H21 to the centroid Cg1 of the C1–C6 ring of a neighbouring molecule, with H21···Cg1i = 2.83 Å, C21···Cg1i = 3.584 (9) Å and C21— H21···Cg1i = 137° [symmetry code: (i) 1 + x, y, z]. The molecules involved in these contacts form a chain parallel to the a axis (Fig. 2).

Experimental top

To a suspension of methylthiophenyl boronic acid, CH3SC6H4-B(OH)2 (0.336 g, 0.2 mmol), in propan-2-ol (10 ml), solid CsCO3 (0.0386 g, 0.2 mmol) was added. After a few minutes of stirring, AuPPh3Cl (0.05 g, 0.1 mmol) was added and a condenser was attached to the reaction flask. The whitish suspension was refluxed at 333 K for 10 h, after which time the liquid looked clear. Clumps of white solid slowly formed. The propan-2-ol solution was then reduced to dryness under vacuum. The dry residue was rinsed with hexane and extracted with benzene (5 ml). Upon layering the benzene solution with hexane, shiny crystals of (I) grew within a week, with a yield of 90%. The sample used in data collection was mounted on a loop using Paratone oil. This compound was also characterized by 1H NMR spectroscopy (CDCl3, δ, p.p.m.): 7.70–7.45 [m, P(C6H5)3], 7.13–7.07 (m, C6H4), 2.5 (s, S—CH3).

Refinement top

The difference peak of 2.96 e Å-3 is 0.81 Å from the Au atom. Rigid-bond restraints on the displacement parameters of C23, C24 and C25 (DELU; three restraints) and isotropic behavior restraints at C24 (ISOR; six restraints) were applied during refinement. All H atoms were placed in calculated positions and refined using a riding model. Aromatic C—H = 0.95 Å, Uiso(H) = 1.2Ueq(C). The H atoms at methyl group C7 were located in a local difference Fourier calculation and refined as riding atoms with a variable torsion angle about the C7—S1 bond (AFIX 137), C—H = 0.98 Å, Uiso(H) = 1.5Ueq(C7). [Please rephrase this section using software-independent terminology]

Computing details top

Data collection: APEX2 (Bruker Nonius, 2008); cell refinement: APEX2 (Bruker Nonius, 2008); data reduction: APEX2 (Bruker Nonius, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The structure of (I), showing the almost linear P—Au—C arrangement.
[Figure 2] Fig. 2. Chain formation in (I), mediated by a weak C—H···π contact. [Symmetry code: (i) 1 + x, y, z].
[2-(methylsulfanyl)phenyl](triphenylphosphine)gold(I) top
Crystal data top
[Au(C7H7S)(C18H15P)]F(000) = 1128
Mr = 582.42Dx = 1.775 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P2ac2abCell parameters from 9913 reflections
a = 6.986 (4) Åθ = 2.4–26.6°
b = 15.553 (9) ŵ = 6.93 mm1
c = 20.060 (12) ÅT = 110 K
V = 2180 (2) Å3Block, colourless
Z = 40.17 × 0.10 × 0.10 mm
Data collection top
Bruker APEXII
diffractometer
4680 independent reflections
Radiation source: fine-focus sealed tube4396 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.135
ω scansθmax = 27.0°, θmin = 1.7°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2006)
h = 88
Tmin = 0.391, Tmax = 0.544k = 1919
24159 measured reflectionsl = 2525
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.042H-atom parameters constrained
wR(F2) = 0.099 w = 1/[σ2(Fo2) + (0.0425P)2 + 4.3846P]
where P = (Fo2 + 2Fc2)/3
S = 1.05(Δ/σ)max = 0.001
4680 reflectionsΔρmax = 2.96 e Å3
254 parametersΔρmin = 1.35 e Å3
9 restraintsAbsolute structure: (Flack, 1983), with how many Friedel pairs?
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.003 (11)
Crystal data top
[Au(C7H7S)(C18H15P)]V = 2180 (2) Å3
Mr = 582.42Z = 4
Orthorhombic, P212121Mo Kα radiation
a = 6.986 (4) ŵ = 6.93 mm1
b = 15.553 (9) ÅT = 110 K
c = 20.060 (12) Å0.17 × 0.10 × 0.10 mm
Data collection top
Bruker APEXII
diffractometer
4680 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 2006)
4396 reflections with I > 2σ(I)
Tmin = 0.391, Tmax = 0.544Rint = 0.135
24159 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.042H-atom parameters constrained
wR(F2) = 0.099Δρmax = 2.96 e Å3
S = 1.05Δρmin = 1.35 e Å3
4680 reflectionsAbsolute structure: (Flack, 1983), with how many Friedel pairs?
254 parametersAbsolute structure parameter: 0.003 (11)
9 restraints
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
xyzUiso*/Ueq
Au10.72064 (4)0.050031 (17)0.776484 (14)0.02846 (10)
S10.7156 (4)0.13156 (14)0.92545 (11)0.0393 (5)
P10.9351 (3)0.08800 (12)0.69512 (10)0.0238 (4)
C10.5167 (12)0.0226 (5)0.8463 (4)0.0298 (17)
C20.5125 (11)0.0643 (5)0.9094 (4)0.0285 (17)
C30.3661 (12)0.0552 (6)0.9541 (4)0.0339 (16)
H30.36830.08550.99520.041*
C40.2148 (14)0.0012 (6)0.9388 (4)0.043 (2)
H40.11400.00640.97000.051*
C50.2087 (13)0.0417 (5)0.8785 (5)0.0417 (19)
H50.10460.07850.86790.050*
C60.3612 (12)0.0297 (4)0.8327 (4)0.0281 (16)
H60.35630.05870.79110.034*
C70.6795 (16)0.1683 (6)1.0085 (5)0.051 (3)
H7A0.56860.20681.00980.076*
H7B0.79360.19931.02370.076*
H7C0.65650.11891.03780.076*
C80.8127 (11)0.1244 (4)0.6198 (3)0.0237 (15)
C90.6742 (12)0.1893 (5)0.6262 (4)0.0353 (19)
H90.65080.21440.66860.042*
C100.5727 (14)0.2167 (6)0.5718 (5)0.044 (2)
H100.47980.26090.57660.053*
C110.6047 (13)0.1804 (6)0.5101 (5)0.042 (2)
H110.53150.19840.47270.050*
C120.7447 (13)0.1173 (5)0.5028 (4)0.0367 (19)
H120.77000.09330.46020.044*
C130.8451 (12)0.0900 (5)0.5570 (4)0.0302 (17)
H130.93940.04660.55160.036*
C141.1012 (10)0.0050 (4)0.6669 (4)0.0238 (15)
C151.0400 (12)0.0816 (5)0.6720 (4)0.0307 (17)
H150.91990.09530.69150.037*
C161.1583 (14)0.1456 (5)0.6482 (4)0.038 (2)
H161.11880.20390.65140.045*
C171.3333 (13)0.1263 (5)0.6198 (4)0.037 (2)
H171.41250.17110.60310.044*
C181.3928 (12)0.0416 (5)0.6157 (4)0.0350 (18)
H181.51400.02830.59690.042*
C191.2761 (12)0.0239 (4)0.6392 (4)0.0282 (15)
H191.31720.08200.63600.034*
C201.0896 (10)0.1767 (4)0.7190 (4)0.0243 (14)
C211.1805 (12)0.1711 (5)0.7808 (4)0.0366 (18)
H211.15310.12440.80980.044*
C221.3102 (14)0.2335 (5)0.7999 (4)0.040 (2)
H221.37170.22960.84200.048*
C231.3508 (12)0.3013 (5)0.7580 (4)0.0312 (16)
H231.44230.34360.77030.037*
C241.2545 (13)0.3065 (5)0.6971 (4)0.0348 (16)
H241.27730.35420.66870.042*
C251.1305 (13)0.2454 (5)0.6780 (4)0.0331 (17)
H251.07010.24960.63570.040*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Au10.02780 (15)0.02841 (14)0.02918 (15)0.00254 (11)0.00644 (11)0.00542 (12)
S10.0361 (11)0.0421 (11)0.0396 (11)0.0094 (10)0.0023 (10)0.0031 (8)
P10.0243 (10)0.0219 (8)0.0253 (9)0.0019 (7)0.0016 (8)0.0007 (7)
C10.033 (4)0.026 (4)0.030 (4)0.001 (3)0.000 (3)0.013 (3)
C20.031 (4)0.023 (4)0.031 (4)0.009 (3)0.010 (3)0.011 (3)
C30.035 (4)0.035 (4)0.031 (4)0.002 (4)0.004 (3)0.007 (4)
C40.036 (5)0.054 (5)0.037 (5)0.004 (4)0.017 (4)0.008 (4)
C50.029 (4)0.035 (4)0.061 (5)0.006 (4)0.008 (4)0.009 (4)
C60.033 (4)0.023 (4)0.028 (4)0.001 (3)0.001 (3)0.004 (3)
C70.053 (7)0.048 (5)0.052 (6)0.021 (5)0.003 (5)0.002 (4)
C80.030 (4)0.016 (3)0.025 (3)0.010 (3)0.000 (3)0.003 (2)
C90.035 (5)0.048 (5)0.023 (4)0.006 (4)0.002 (3)0.001 (3)
C100.034 (5)0.056 (6)0.043 (5)0.010 (4)0.001 (4)0.010 (4)
C110.035 (5)0.054 (6)0.036 (5)0.011 (4)0.010 (4)0.018 (4)
C120.042 (6)0.040 (4)0.028 (4)0.007 (4)0.000 (4)0.003 (3)
C130.034 (4)0.023 (3)0.033 (4)0.002 (3)0.004 (3)0.000 (3)
C140.024 (4)0.023 (3)0.025 (4)0.001 (3)0.000 (3)0.004 (3)
C150.037 (4)0.023 (3)0.032 (4)0.003 (3)0.004 (4)0.008 (3)
C160.045 (5)0.023 (4)0.045 (5)0.001 (4)0.004 (4)0.005 (4)
C170.042 (5)0.034 (4)0.035 (4)0.014 (4)0.008 (4)0.009 (3)
C180.025 (4)0.037 (4)0.043 (4)0.004 (4)0.000 (3)0.002 (4)
C190.024 (4)0.025 (3)0.036 (4)0.004 (3)0.008 (3)0.003 (3)
C200.021 (3)0.020 (3)0.032 (4)0.002 (2)0.003 (3)0.006 (3)
C210.042 (5)0.031 (4)0.037 (4)0.004 (3)0.011 (4)0.006 (3)
C220.054 (6)0.029 (4)0.037 (4)0.001 (4)0.024 (4)0.001 (3)
C230.030 (4)0.024 (3)0.039 (4)0.005 (3)0.001 (3)0.005 (3)
C240.048 (4)0.022 (3)0.035 (3)0.006 (3)0.003 (3)0.007 (2)
C250.041 (5)0.029 (4)0.030 (4)0.010 (3)0.005 (3)0.005 (3)
Geometric parameters (Å, º) top
Au1—C12.042 (8)C11—H110.9500
Au1—P12.293 (2)C12—C131.360 (11)
S1—C71.779 (10)C12—H120.9500
S1—C21.792 (8)C13—H130.9500
P1—C201.816 (7)C14—C191.374 (11)
P1—C81.825 (7)C14—C151.417 (10)
P1—C141.826 (7)C15—C161.379 (12)
C1—C61.384 (11)C15—H150.9500
C1—C21.423 (11)C16—C171.382 (13)
C2—C31.368 (10)C16—H160.9500
C3—C41.385 (13)C17—C181.384 (12)
C3—H30.9500C17—H170.9500
C4—C51.382 (13)C18—C191.387 (11)
C4—H40.9500C18—H180.9500
C5—C61.418 (12)C19—H190.9500
C5—H50.9500C20—C251.379 (10)
C6—H60.9500C20—C211.395 (11)
C7—H7A0.9800C21—C221.381 (12)
C7—H7B0.9800C21—H210.9500
C7—H7C0.9800C22—C231.378 (11)
C8—C131.388 (10)C22—H220.9500
C8—C91.404 (11)C23—C241.397 (12)
C9—C101.368 (12)C23—H230.9500
C9—H90.9500C24—C251.341 (11)
C10—C111.378 (13)C24—H240.9500
C10—H100.9500C25—H250.9500
C11—C121.394 (13)
C1—Au1—P1175.9 (2)C12—C11—H11120.1
C7—S1—C2104.1 (4)C13—C12—C11119.8 (8)
C20—P1—C8105.2 (3)C13—C12—H12120.1
C20—P1—C14104.0 (3)C11—C12—H12120.1
C8—P1—C14105.1 (3)C12—C13—C8121.4 (7)
C20—P1—Au1113.3 (3)C12—C13—H13119.3
C8—P1—Au1111.3 (3)C8—C13—H13119.3
C14—P1—Au1117.0 (3)C19—C14—C15120.1 (7)
C6—C1—C2115.2 (7)C19—C14—P1122.6 (5)
C6—C1—Au1122.4 (6)C15—C14—P1117.3 (6)
C2—C1—Au1122.0 (6)C16—C15—C14118.7 (8)
C3—C2—C1123.5 (8)C16—C15—H15120.6
C3—C2—S1122.3 (6)C14—C15—H15120.6
C1—C2—S1114.2 (6)C15—C16—C17121.1 (8)
C2—C3—C4119.2 (8)C15—C16—H16119.5
C2—C3—H3120.4C17—C16—H16119.5
C4—C3—H3120.4C16—C17—C18119.8 (8)
C5—C4—C3120.7 (8)C16—C17—H17120.1
C5—C4—H4119.6C18—C17—H17120.1
C3—C4—H4119.6C17—C18—C19120.2 (8)
C4—C5—C6118.7 (8)C17—C18—H18119.9
C4—C5—H5120.7C19—C18—H18119.9
C6—C5—H5120.7C14—C19—C18120.2 (7)
C1—C6—C5122.7 (8)C14—C19—H19119.9
C1—C6—H6118.7C18—C19—H19119.9
C5—C6—H6118.7C25—C20—C21118.9 (7)
S1—C7—H7A109.5C25—C20—P1123.7 (6)
S1—C7—H7B109.5C21—C20—P1117.3 (5)
H7A—C7—H7B109.5C22—C21—C20120.1 (7)
S1—C7—H7C109.5C22—C21—H21120.0
H7A—C7—H7C109.5C20—C21—H21120.0
H7B—C7—H7C109.5C23—C22—C21120.3 (7)
C13—C8—C9118.1 (7)C23—C22—H22119.9
C13—C8—P1123.8 (6)C21—C22—H22119.9
C9—C8—P1118.1 (5)C22—C23—C24118.6 (7)
C10—C9—C8120.6 (8)C22—C23—H23120.7
C10—C9—H9119.7C24—C23—H23120.7
C8—C9—H9119.7C25—C24—C23121.3 (7)
C9—C10—C11120.2 (9)C25—C24—H24119.4
C9—C10—H10119.9C23—C24—H24119.4
C11—C10—H10119.9C24—C25—C20120.9 (8)
C10—C11—C12119.8 (8)C24—C25—H25119.6
C10—C11—H11120.1C20—C25—H25119.6
C6—C1—C2—C30.7 (11)C8—P1—C14—C1981.2 (7)
Au1—C1—C2—C3172.0 (6)Au1—P1—C14—C19154.8 (5)
C6—C1—C2—S1179.9 (5)C20—P1—C14—C15153.4 (6)
Au1—C1—C2—S17.3 (8)C8—P1—C14—C1596.3 (7)
C7—S1—C2—C34.6 (8)Au1—P1—C14—C1527.6 (7)
C7—S1—C2—C1176.1 (6)C19—C14—C15—C160.6 (12)
C1—C2—C3—C41.6 (12)P1—C14—C15—C16177.0 (6)
S1—C2—C3—C4179.2 (6)C14—C15—C16—C170.0 (13)
C2—C3—C4—C51.4 (13)C15—C16—C17—C180.8 (13)
C3—C4—C5—C60.3 (13)C16—C17—C18—C191.0 (12)
C2—C1—C6—C50.5 (11)C15—C14—C19—C180.4 (11)
Au1—C1—C6—C5173.1 (6)P1—C14—C19—C18177.0 (6)
C4—C5—C6—C10.7 (12)C17—C18—C19—C140.4 (12)
C20—P1—C8—C13111.2 (7)C8—P1—C20—C2513.2 (7)
C14—P1—C8—C131.8 (7)C14—P1—C20—C2597.0 (7)
Au1—P1—C8—C13125.8 (6)Au1—P1—C20—C25135.0 (6)
C20—P1—C8—C970.5 (7)C8—P1—C20—C21171.0 (6)
C14—P1—C8—C9179.9 (6)C14—P1—C20—C2178.8 (6)
Au1—P1—C8—C952.5 (6)Au1—P1—C20—C2149.3 (6)
C13—C8—C9—C101.0 (12)C25—C20—C21—C220.5 (12)
P1—C8—C9—C10177.4 (7)P1—C20—C21—C22175.4 (7)
C8—C9—C10—C110.3 (14)C20—C21—C22—C230.1 (14)
C9—C10—C11—C121.8 (14)C21—C22—C23—C241.6 (13)
C10—C11—C12—C131.9 (13)C22—C23—C24—C252.6 (13)
C11—C12—C13—C80.6 (12)C23—C24—C25—C202.0 (13)
C9—C8—C13—C120.8 (11)C21—C20—C25—C240.4 (12)
P1—C8—C13—C12177.5 (6)P1—C20—C25—C24176.1 (7)
C20—P1—C14—C1929.1 (7)

Experimental details

Crystal data
Chemical formula[Au(C7H7S)(C18H15P)]
Mr582.42
Crystal system, space groupOrthorhombic, P212121
Temperature (K)110
a, b, c (Å)6.986 (4), 15.553 (9), 20.060 (12)
V3)2180 (2)
Z4
Radiation typeMo Kα
µ (mm1)6.93
Crystal size (mm)0.17 × 0.10 × 0.10
Data collection
DiffractometerBruker APEXII
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 2006)
Tmin, Tmax0.391, 0.544
No. of measured, independent and
observed [I > 2σ(I)] reflections
24159, 4680, 4396
Rint0.135
(sin θ/λ)max1)0.638
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.042, 0.099, 1.05
No. of reflections4680
No. of parameters254
No. of restraints9
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)2.96, 1.35
Absolute structure(Flack, 1983), with how many Friedel pairs?
Absolute structure parameter0.003 (11)

Computer programs: APEX2 (Bruker Nonius, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), SHELXTL (Sheldrick, 2008).

Main structural features of linear (phosphine)(ortho-substituted-phenyl)gold(I) compounds top
CompoundSpace groupAu—PAu—CP—Au—C
C38H32Au2P (Bennett et al., 2004)P21/a2.295, 2.2972.011, 2.062176.8, 175.9
C30H24AuOP (Baukanova et al., 1994)P12.2882.040179.5
C48H38Au2OP2 (Baukanova et al., 1994)P21/c2.269, 2.2802.052, 2.059174.8, 174.7
C27H35AuP+.SbF6- (Herrero-Gomez et al., 2006)P21/n2.2643 (10)2.299 (5), 2.423 (5)a157.2, 164.9
C30H42AuP (Partyka et al., 2006)P12.2912.051174.5
C24H20AuP (Hong et al., 1994)P12.296 (2), 2.2952.045 (6), 2.054175.5 (2), 177.6
C37H32Au2P2 (Hong et al., 1994)C2/c2.300 (2)2.07 (2)175.8 (4)
C50H42Au2P2.CH2Cl2 (Baukanova et al., 1997)P21/c2.279 (8)2.05 (2)174.5 (5)
C30H24AuP (Osawa et al., 2007)P12.2852.055177.1
C53H77Au2NP2 (Kui et al., 2006)C2/c2.302 (9), 2.302 (13)2.053 (9), 2.059 (13)175.82 (19), 177.93 (22)
C18H32AuP (Sladek et al., 1995)P21/n2.305 (1)2.055 (6)177.9 (2)
C44H38Au2P2 (Sladek et al., 1995)P12.284 (1)2.044 (4)174.8 (2)
C39H34Au2P2.2C6H6 (Baukanova et al., 1997)P212.296 (5), 2.296 (4)2.04 (2), 2.05 (2)179.0 (5), 168.6 (4)
C13H20AuN3P+.C24H20B- (Forward et al., 1995)P21/n2.274 (3)2.04 (1)176.5 (5)
C12H17AuN3P (Forward et al., 1995)P21/n2.289 (5)2.040 (2)170.1 (5)
This workP2121212.293 (2)2.042 (8)175.9 (2)
Note: (a) π side-on gold–phenyl ring bond.
 

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