Chlorido{[(E)-2-(diphenyl­phosphan­yl)benzyl­idene](furan-2-ylmeth­yl)amine-κP}gold(I)

Chiririwa, H.; Davis, W.L.

doi:10.1107/S1600536812050404

metal-organic compounds

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Volume 69| Part 1| January 2013| Page m53

https://doi.org/10.1107/S1600536812050404

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Chlorido{[(E)-2-(diphenylphosphanyl)benzylidene](furan-2-ylmethyl)amine-κP}gold(I)

Haleden Chiririwa ^a ^* and Wade L. Davis ^b

^aDepartment of Chemistry, University of Cape Town, Private Bag, Rondebosch 7707, South Africa, and ^bResearch Centre for Synthesis and Catalysis, Department of Chemistry, University of Johannesburg (APK Campus), PO Box 524, Auckland Park, Johannesburg, 2006, South Africa
^*Correspondence e-mail: harrychiririwa@yahoo.com

(Received 21 November 2012; accepted 11 December 2012; online 15 December 2012)

In the title complex, [AuCl(C₂₄H₂₀NOP)], the ligand has N, P and O electron-donating atoms but the Au^I atom is coordinated only by the `soft' P atom and an additional Cl atom in an almost linear fashion. Important geometrical parameters include Au—P = 2.2321 (13) Å, Au—Cl = 2.2820 (13) Å and P—Au—Cl = 176.49 (5)°. The furan ring is disordered over two positions in a 0.51 (2):0.49 (2) ratio.

Related literature

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 ).

Experimental

Crystal data

[AuCl(C₂₄H₂₀NOP)]
M_r = 601.80
Monoclinic, P 2₁ /n
a = 13.4559 (4) Å
b = 10.3917 (2) Å
c = 17.2641 (4) Å
β = 111.751 (1)°
V = 2242.16 (9) Å³
Z = 4
Mo Kα radiation
μ = 6.77 mm⁻¹
T = 173 K
0.16 × 0.11 × 0.02 mm

Data collection

Bruker APEXII 4K CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2007 ) T_min = 0.411, T_max = 0.877
74340 measured reflections
5536 independent reflections
4175 reflections with I > 2σ(I)
R_int = 0.100

Refinement

R[F² > 2σ(F²)] = 0.039
wR(F²) = 0.100
S = 1.07
5536 reflections
299 parameters
240 restraints
H-atom parameters constrained
Δρ_max = 2.27 e Å⁻³
Δρ_min = −1.52 e Å⁻³

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).

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536812050404/yk2081sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812050404/yk2081Isup2.hkl

checkCIF report

Comment top

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..

Related literature top

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).

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-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.

Structure description top

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).

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: 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).

Figures top

Fig. 1. View of [Au(C₂₄H₂₀NOP)Cl] showing the atom labelling scheme and displacement ellipsoids drawn at the 40% probability level.

Chlorido{[(E)-2-(diphenylphosphanyl)benzylidene](furan-2- ylmethyl)amine-κP}gold(I) top

Crystal data top

[AuCl(C₂₄H₂₀NOP)]	F(000) = 1160
M_r = 601.80	D_x = 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

Data collection top

Bruker APEXII 4K CCD diffractometer	5536 independent reflections
Radiation source: fine-focus sealed tube	4175 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.100
Detector resolution: 0 pixels mm^-1	θ_max = 28.3°, θ_min = 3.1°
0.5° ω scans, 20s	h = −17→17
Absorption correction: multi-scan (SADABS; Bruker, 2007)	k = −13→13
T_min = 0.411, T_max = 0.877	l = −23→23
74340 measured reflections

Refinement top

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(F_o²) + (0.0574P)²] where P = (F_o² + 2F_c²)/3
5536 reflections	(Δ/σ)_max = 0.003
299 parameters	Δρ_max = 2.27 e Å⁻³
240 restraints	Δρ_min = −1.52 e Å⁻³

Crystal data top

[AuCl(C₂₄H₂₀NOP)]	V = 2242.16 (9) Å³
M_r = 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)°

Data collection top

Bruker APEXII 4K CCD diffractometer	5536 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2007)	4175 reflections with I > 2σ(I)
T_min = 0.411, T_max = 0.877	R_int = 0.100
74340 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	240 restraints
wR(F²) = 0.100	H-atom parameters constrained
S = 1.07	Δρ_max = 2.27 e Å⁻³
5536 reflections	Δρ_min = −1.52 e Å⁻³
299 parameters

Special details top

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

	x	y	z	U_iso*/U_eq	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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)]
M_r	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)
T_min, T_max	0.411, 0.877
No. of measured, independent and observed [I > 2σ(I)] reflections	74340, 5536, 4175
R_int	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
Δρ_max, Δρ_min (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).

Acknowledgements

Mintek and Project AuTEK are acknowledged for funding this project.

References

Barnard, P. J., Baker, M. V., Berners-Price, S. J. & Day, D. A. (2004). J. Inorg. Biochem. 98, 115-119. Web of Science CrossRef Google Scholar
Brandenburg, K. & Putz, H. (2005). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Bruker (2007). APEX2, SADABS, SAINT and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Chiririwa, H., Moss, J. R., Hendricks, D., Smith, G. S. & Meijboom, R. (2013). Polyhedron, 49, 29–35. Web of Science CSD CrossRef CAS Google Scholar
Chiririwa, H. & Muller, A. (2012). Acta Cryst. E68, m49. Web of Science CSD CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
Mogorosi, M. M., Mahamo, T., Moss, J. R., Mapolie, S. F., Slootweg, J. C., Lammertsma, K. & Smith, G. S. (2011). J. Organomet. Chem. 696, 3585–3592. Web of Science CrossRef CAS Google Scholar
Nomiya, K., Yamamoto, S., Noguchi, R., Yokoyama, H., Kasuga, N. C., Ohyama, K. & Kato, C. (2003). J. Inorg. Biochem. 95, 2208–220. Web of Science CSD CrossRef Google Scholar
Shaw, C. F. III (1999). Chem. Rev. 99, 2589–2600. Web of Science CrossRef PubMed CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Uson, R. & Laguna, A. (1986). Organometallic Synthesis, Vol. 3, edited by R. B. Lang & J. J. Eish, pp. 324–327. Amsterdam: Elsevier. Google Scholar
Williams, D. B. G., Traut, T., Kriel, F. H. & van Zyl, W. E. (2007). Inorg. Chem. Commun. 10, 538–542. Web of Science CSD CrossRef CAS Google Scholar

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