{μ-1,2-Bis[bis­(4-meth­oxy­phen­yl)phosphan­yl]-1,2-diethyl­hydrazine-κ2P:P′}bis­[chloridogold(I)] tetra­hydro­furan disolvate

Kriel, F.H.; Fernandes, M.A.; Coates, J.

doi:10.1107/S1600536811038499

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 10| October 2011| Page m1426

https://doi.org/10.1107/S1600536811038499

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{μ-1,2-Bis[bis(4-methoxyphenyl)phosphanyl]-1,2-diethylhydrazine-κ²P:P′}bis[chloridogold(I)] tetrahydrofuran disolvate

Frederik H. Kriel,^a ^* Manuel A. Fernandes ^b and Judy Coates ^a

^aAuTEK, Mintek, Private Bag X3015, Randburg, 2125, South Africa, and ^bMolecular Science Institute, School of Chemistry, University of the Witwatersrand, PO Wits, 2050, Johannesburg, South Africa
^*Correspondence e-mail: erikk@mintek.co.za

(Received 30 August 2011; accepted 20 September 2011; online 30 September 2011)

The title compound, [Au₂Cl₂(C₃₂H₃₈N₂O₄P₂)]·2C₄H₈O, is formed from a bidentate phosphine ligand complexed to two linear gold(I) nuclei [P—Au—Cl = 175.98 (3)°]. The nuclei are 3.1414 (2) Å apart. The molecule exhibits a twofold symmetry axis. Stacks of the compound are formed through intermolecular C—H⋯Cl interactions, while the tetrahydrofuran (THF) solvate is further attached to the stacks through weak C—H⋯O hydrogen bonding from the THF O atom to two separate H atoms on the complex.

Related literature

For the synthesis of the parent ligand and related structures utilizing alternative metals see: Reddy et al. (1994 , 1995 ); Slawin et al. (2002 ); Kriel et al. (2011a ,b ,c). For Au⋯Au interactions, see: Holleman & Wiberg (2001 ). For the biological activity of the title complex, see: Fonteh & Meyer (2009 ).

Experimental

Crystal data

[Au₂Cl₂(C₃₂H₃₈N₂O₄P₂)]·2C₄H₈O
M_r = 1185.63
Monoclinic, C 2/c
a = 23.6375 (4) Å
b = 9.1260 (1) Å
c = 20.2269 (3) Å
β = 93.976 (1)°
V = 4352.76 (11) Å³
Z = 4
Mo Kα radiation
μ = 6.98 mm⁻¹
T = 173 K
0.36 × 0.20 × 0.07 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: integration (SADABS; Bruker, 1999 ) T_min = 0.188, T_max = 0.641
38471 measured reflections
5253 independent reflections
4694 reflections with I > 2σ(I)
R_int = 0.046

Refinement

R[F² > 2σ(F²)] = 0.022
wR(F²) = 0.059
S = 1.05
5253 reflections
244 parameters
H-atom parameters constrained
Δρ_max = 1.74 e Å⁻³
Δρ_min = −0.64 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1A⋯Clⁱ	0.99	2.80	3.592 (3)	137
C15—H15⋯O3ⁱⁱ	0.95	2.63	3.497 (5)	152
C17—H17B⋯O3ⁱⁱ	0.98	2.53	3.444 (7)	156
Symmetry codes: (i) $[-x+2, y-1, -z+{\script{3\over 2}}]$ ; (ii) x, y+1, z.

Data collection: APEX2 (Bruker, 1999); cell refinement: SAINT-Plus (Bruker, 1999); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2006 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks I, New_Global_Publ_Block. DOI: https://doi.org/10.1107/S1600536811038499/bh2379sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536811038499/bh2379Isup2.hkl

checkCIF report

Comment top

The title compound, C₃₂H₃₈Au₂Cl₂N₂O₄P₂.2(C₄H₈O), formed from a bidentate phosphine ligand complexed to two linear gold(I) nuclei, readily crystallizes out of dichloromethane (DCM) with the addition of a few drops of tetrahydrofuran (THF). The crystal structure includes two THF solvent molecules. The complex molecule is bisected by a twofold axis through the N—N' and Au—Au' lines (Fig. 1). Gold(I) has an almost linear coordination with a P—Au—Cl angle of 175.98 (3)°. The Au—Au distance within the complex is 3.141 (2) Å, well within the range of aurophilic interactions (described in Holleman & Wiberg, 2001, as being normally between 2.7 Å and 3.4 Å). Other bond lengths are within expected ranges.

The structure exhibits columns of complexes arranged head-to-tail along b, forming channels filled with THF. There is an intracolumnar contact involving Cl atoms in one molecule and H atoms on the ethyl substituted hydrazine bridge of a neighboring one, in the same column (Cl···H1Aⁱ: 2.80 Å, (i): 2-x, -1+y, 3/2-z; site A in Fig. 2). There are also weak intercolumnar H-bonding contacts (O1···H13ⁱⁱ: 2.61 Å, (ii): 3/2-x, 1/2-y, 1-z; site B in Fig. 2). Finally, the THF solvate molecule is weakly attached to the columns by a pair of O···H contacts (O3···H15 = 2.63 Å, O3···H17B = 2.53 Å; site C in Fig. 2).

The biological activity of the title complex is discussed in Fonteh & Meyer (2009), and related structures with other dialkyl hydrazine derivatives have been also reported (Kriel et al., 2011a,b,c; Reddy et al., 1994, 1995; Slawin et al., 2002).

Related literature top

For the synthesis of the parent ligand and related structures utilizing alternative metals see: Reddy et al. (1994, 1995); Slawin et al. (2002); Kriel et al. (2011a,b,c). For Au···Au interactions, see: Holleman & Wiberg (2001). For the biological activity of the title complex, see: Fonteh & Meyer (2009).

Experimental top

The complex was synthesized by dissolving tetrahydrothiophenegold(I) chloride [(THT)AuCl] in DCM and adding 0.5 equivalents of the corresponding ligand, bis(di(4-methoxyphenyl)phosphino)-1,2-diethylhydrazine. The addition of a few drops of THF led to the growth of crystals suitable for use in single-crystal X-Ray analysis. The presence of THF during the initial complexation led to undesirable side products as a result of the breakdown of the ligand.

Structure description top

For the synthesis of the parent ligand and related structures utilizing alternative metals see: Reddy et al. (1994, 1995); Slawin et al. (2002); Kriel et al. (2011a,b,c). For Au···Au interactions, see: Holleman & Wiberg (2001). For the biological activity of the title complex, see: Fonteh & Meyer (2009).

Computing details top

Data collection: APEX2 (Bruker, 1999); cell refinement: SAINT-Plus (Bruker, 1999); data reduction: SAINT-Plus (Bruker, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2006); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

	Fig. 1. Molecular structure of the title complex drawn with displacement ellipsoids at the 50% probability level. Hydrogen atoms and solvent THF have been omitted for clarity.
	Fig. 2. Packing of the title compound showing short contacts (dashed lines).

{µ-1,2-Bis[bis(4-methoxyphenyl)phosphanyl]-1,2-diethylhydrazine- κ²P:P'}bis[chloridogold(I)] tetrahydrofuran disolvate top

Crystal data top

[Au₂Cl₂(C₃₂H₃₈N₂O₄P₂)]·2C₄H₈O	F(000) = 2312
M_r = 1185.63	D_x = 1.809 Mg m⁻³
Monoclinic, C2/c	Melting point: 369 K
Hall symbol: -C 2yc	Mo Kα radiation, λ = 0.71073 Å
a = 23.6375 (4) Å	Cell parameters from 7364 reflections
b = 9.1260 (1) Å	θ = 2.4–34.2°
c = 20.2269 (3) Å	µ = 6.98 mm⁻¹
β = 93.976 (1)°	T = 173 K
V = 4352.76 (11) Å³	Plate, colourless
Z = 4	0.36 × 0.20 × 0.07 mm

Data collection top

Bruker APEXII CCD diffractometer	5253 independent reflections
Radiation source: fine-focus sealed tube	4694 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.046
φ and ω scans	θ_max = 28.0°, θ_min = 1.7°
Absorption correction: integration (SADABS; Bruker, 1999)	h = −31→31
T_min = 0.188, T_max = 0.641	k = −12→12
38471 measured reflections	l = −26→26

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)] = 0.022	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.059	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0337P)² + 7.339P] where P = (F_o² + 2F_c²)/3
5253 reflections	(Δ/σ)_max = 0.011
244 parameters	Δρ_max = 1.74 e Å⁻³
0 restraints	Δρ_min = −0.64 e Å⁻³
0 constraints

Crystal data top

[Au₂Cl₂(C₃₂H₃₈N₂O₄P₂)]·2C₄H₈O	V = 4352.76 (11) Å³
M_r = 1185.63	Z = 4
Monoclinic, C2/c	Mo Kα radiation
a = 23.6375 (4) Å	µ = 6.98 mm⁻¹
b = 9.1260 (1) Å	T = 173 K
c = 20.2269 (3) Å	0.36 × 0.20 × 0.07 mm
β = 93.976 (1)°

Data collection top

Bruker APEXII CCD diffractometer	5253 independent reflections
Absorption correction: integration (SADABS; Bruker, 1999)	4694 reflections with I > 2σ(I)
T_min = 0.188, T_max = 0.641	R_int = 0.046
38471 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.022	0 restraints
wR(F²) = 0.059	H-atom parameters constrained
S = 1.05	Δρ_max = 1.74 e Å⁻³
5253 reflections	Δρ_min = −0.64 e Å⁻³
244 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
C1	0.93455 (12)	0.1681 (3)	0.72815 (16)	0.0287 (6)
H1A	0.9526	0.0814	0.7502	0.034*
H1B	0.9217	0.1393	0.6824	0.034*
C2	0.88305 (13)	0.2110 (4)	0.76481 (18)	0.0385 (8)
H2A	0.8564	0.1286	0.7643	0.058*
H2B	0.8644	0.2958	0.7430	0.058*
H2C	0.8951	0.2362	0.8107	0.058*
C11	0.91251 (13)	0.4084 (3)	0.62384 (15)	0.0247 (6)
C12	0.88945 (13)	0.3154 (4)	0.57400 (16)	0.0335 (7)
H12	0.9132	0.2472	0.5537	0.040*
C13	0.83239 (14)	0.3221 (4)	0.55403 (18)	0.0415 (8)
H13	0.8171	0.2584	0.5202	0.050*
C14	0.79741 (14)	0.4216 (4)	0.58318 (18)	0.0365 (7)
C15	0.81971 (14)	0.5188 (4)	0.63099 (16)	0.0336 (7)
H15	0.7962	0.5902	0.6496	0.040*
C16	0.87698 (13)	0.5096 (3)	0.65111 (15)	0.0287 (6)
H16	0.8923	0.5745	0.6845	0.034*
C17	0.70206 (17)	0.4959 (6)	0.5975 (3)	0.0676 (14)
H17A	0.6636	0.4817	0.5772	0.101*
H17B	0.7118	0.6003	0.5966	0.101*
H17C	0.7038	0.4617	0.6435	0.101*
C21	1.01949 (12)	0.2838 (3)	0.59644 (14)	0.0245 (6)
C22	1.02334 (13)	0.1309 (3)	0.59963 (15)	0.0268 (6)
H22	1.0068	0.0799	0.6344	0.032*
C23	1.05087 (13)	0.0534 (3)	0.55277 (16)	0.0288 (6)
H23	1.0540	−0.0502	0.5560	0.035*
C24	1.07393 (13)	0.1270 (4)	0.50081 (16)	0.0294 (6)
C25	1.07051 (14)	0.2790 (4)	0.49653 (16)	0.0341 (7)
H25	1.0862	0.3294	0.4610	0.041*
C26	1.04377 (13)	0.3562 (3)	0.54489 (16)	0.0295 (6)
H26	1.0421	0.4601	0.5427	0.035*
C27	1.1244 (3)	0.1104 (5)	0.4032 (3)	0.0730 (17)
H27A	1.1420	0.0368	0.3759	0.109*
H27B	1.1533	0.1806	0.4201	0.109*
H27C	1.0947	0.1623	0.3763	0.109*
C44	0.7033 (5)	−0.0784 (7)	0.5960 (4)	0.128 (4)
H44A	0.7209	−0.0644	0.5534	0.154*
H44B	0.6678	−0.1352	0.5877	0.154*
O3	0.74324 (16)	−0.1558 (4)	0.6450 (2)	0.0791 (10)
C41	0.75325 (17)	−0.0776 (5)	0.7055 (2)	0.0461 (9)
H41A	0.7941	−0.0731	0.7198	0.055*
H41B	0.7321	−0.1202	0.7415	0.055*
C42	0.7289 (4)	0.0785 (8)	0.6826 (4)	0.115 (3)
H42A	0.7078	0.1229	0.7183	0.138*
H42B	0.7603	0.1450	0.6729	0.138*
N	0.97751 (9)	0.2854 (3)	0.72518 (11)	0.0227 (5)
P	0.98471 (3)	0.38920 (7)	0.65760 (4)	0.02138 (14)
Cl	1.08170 (4)	0.80680 (9)	0.70523 (5)	0.0473 (2)
Au	1.029954 (5)	0.597871 (11)	0.683068 (5)	0.02524 (5)
O1	0.74131 (11)	0.4147 (3)	0.56141 (16)	0.0535 (8)
O2	1.10005 (11)	0.0398 (3)	0.45758 (13)	0.0411 (6)
C43	0.6922 (5)	0.0576 (11)	0.6251 (5)	0.165 (5)
H43A	0.6523	0.0608	0.6370	0.198*
H43B	0.6979	0.1374	0.5930	0.198*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0257 (14)	0.0246 (14)	0.0351 (16)	−0.0070 (11)	−0.0025 (12)	0.0033 (12)
C2	0.0240 (14)	0.0454 (19)	0.0458 (19)	−0.0060 (14)	0.0009 (13)	0.0105 (16)
C11	0.0255 (13)	0.0239 (14)	0.0241 (13)	0.0025 (11)	−0.0019 (11)	0.0018 (11)
C12	0.0314 (15)	0.0355 (17)	0.0331 (16)	0.0056 (13)	−0.0025 (13)	−0.0108 (14)
C13	0.0344 (17)	0.047 (2)	0.0407 (19)	0.0064 (15)	−0.0116 (14)	−0.0181 (16)
C14	0.0280 (15)	0.0442 (19)	0.0360 (18)	0.0052 (14)	−0.0073 (13)	−0.0009 (14)
C15	0.0317 (16)	0.0338 (17)	0.0350 (16)	0.0087 (13)	−0.0009 (13)	−0.0030 (14)
C16	0.0304 (15)	0.0286 (15)	0.0262 (14)	0.0046 (12)	−0.0028 (12)	−0.0043 (12)
C17	0.0301 (19)	0.080 (3)	0.091 (4)	0.018 (2)	−0.009 (2)	−0.020 (3)
C21	0.0239 (13)	0.0236 (14)	0.0256 (14)	0.0011 (11)	−0.0011 (11)	−0.0025 (11)
C22	0.0289 (15)	0.0243 (14)	0.0273 (15)	−0.0001 (11)	0.0017 (12)	0.0004 (11)
C23	0.0283 (15)	0.0234 (14)	0.0344 (16)	0.0030 (12)	−0.0003 (12)	−0.0045 (12)
C24	0.0251 (14)	0.0310 (15)	0.0324 (16)	0.0009 (12)	0.0033 (12)	−0.0081 (13)
C25	0.0397 (17)	0.0331 (17)	0.0304 (16)	−0.0013 (14)	0.0099 (13)	−0.0006 (13)
C26	0.0338 (16)	0.0249 (14)	0.0301 (16)	0.0027 (12)	0.0051 (13)	0.0019 (12)
C27	0.097 (4)	0.057 (3)	0.073 (3)	−0.025 (3)	0.058 (3)	−0.029 (2)
C44	0.237 (11)	0.060 (4)	0.077 (4)	0.002 (5)	−0.059 (6)	0.001 (3)
O3	0.071 (2)	0.072 (2)	0.094 (3)	0.0068 (19)	−0.001 (2)	−0.015 (2)
C41	0.0394 (19)	0.057 (2)	0.042 (2)	−0.0079 (17)	0.0039 (16)	−0.0123 (18)
C42	0.172 (9)	0.085 (5)	0.087 (5)	0.024 (5)	0.011 (5)	−0.013 (4)
N	0.0215 (11)	0.0234 (11)	0.0228 (11)	−0.0029 (9)	−0.0022 (9)	0.0016 (9)
P	0.0227 (3)	0.0190 (3)	0.0222 (3)	0.0010 (3)	0.0003 (3)	−0.0005 (3)
Cl	0.0596 (6)	0.0271 (4)	0.0557 (5)	−0.0170 (4)	0.0083 (4)	−0.0046 (4)
Au	0.03037 (7)	0.01883 (7)	0.02676 (7)	−0.00279 (4)	0.00365 (4)	0.00018 (4)
O1	0.0284 (12)	0.069 (2)	0.0603 (18)	0.0115 (12)	−0.0135 (12)	−0.0204 (14)
O2	0.0434 (14)	0.0348 (13)	0.0473 (14)	−0.0030 (11)	0.0187 (11)	−0.0139 (11)
C43	0.239 (12)	0.156 (8)	0.101 (6)	0.127 (9)	0.019 (7)	0.032 (6)

Geometric parameters (Å, º) top

C1—N	1.480 (4)	C23—H23	0.9500
C1—C2	1.520 (5)	C24—O2	1.362 (4)
C1—H1A	0.9900	C24—C25	1.392 (5)
C1—H1B	0.9900	C25—C26	1.393 (4)
C2—H2A	0.9800	C25—H25	0.9500
C2—H2B	0.9800	C26—H26	0.9500
C2—H2C	0.9800	C27—O2	1.430 (5)
C11—C16	1.389 (4)	C27—H27A	0.9800
C11—C12	1.399 (4)	C27—H27B	0.9800
C11—P	1.802 (3)	C27—H27C	0.9800
C12—C13	1.382 (4)	C44—C43	1.406 (10)
C12—H12	0.9500	C44—O3	1.498 (8)
C13—C14	1.387 (5)	C44—H44A	0.9900
C13—H13	0.9500	C44—H44B	0.9900
C14—O1	1.369 (4)	O3—C41	1.423 (5)
C14—C15	1.389 (5)	C41—C42	1.594 (8)
C15—C16	1.389 (4)	C41—H41A	0.9900
C15—H15	0.9500	C41—H41B	0.9900
C16—H16	0.9500	C42—C43	1.415 (12)
C17—O1	1.427 (5)	C42—H42A	0.9900
C17—H17A	0.9800	C42—H42B	0.9900
C17—H17B	0.9800	N—Nⁱ	1.411 (4)
C17—H17C	0.9800	N—P	1.681 (2)
C21—C26	1.392 (4)	P—Au	2.2269 (7)
C21—C22	1.400 (4)	Cl—Au	2.2927 (8)
C21—P	1.809 (3)	Au—Auⁱ	3.1414 (2)
C22—C23	1.381 (4)	C43—H43A	0.9900
C22—H22	0.9500	C43—H43B	0.9900
C23—C24	1.390 (5)

N—C1—C2	114.1 (3)	C26—C25—H25	120.4
N—C1—H1A	108.7	C21—C26—C25	121.1 (3)
C2—C1—H1A	108.7	C21—C26—H26	119.4
N—C1—H1B	108.7	C25—C26—H26	119.4
C2—C1—H1B	108.7	O2—C27—H27A	109.5
H1A—C1—H1B	107.6	O2—C27—H27B	109.5
C1—C2—H2A	109.5	H27A—C27—H27B	109.5
C1—C2—H2B	109.5	O2—C27—H27C	109.5
H2A—C2—H2B	109.5	H27A—C27—H27C	109.5
C1—C2—H2C	109.5	H27B—C27—H27C	109.5
H2A—C2—H2C	109.5	C43—C44—O3	105.4 (6)
H2B—C2—H2C	109.5	C43—C44—H44A	110.7
C16—C11—C12	118.3 (3)	O3—C44—H44A	110.7
C16—C11—P	119.8 (2)	C43—C44—H44B	110.7
C12—C11—P	121.7 (2)	O3—C44—H44B	110.7
C13—C12—C11	120.5 (3)	H44A—C44—H44B	108.8
C13—C12—H12	119.8	C41—O3—C44	113.2 (4)
C11—C12—H12	119.8	O3—C41—C42	99.3 (4)
C12—C13—C14	120.2 (3)	O3—C41—H41A	111.9
C12—C13—H13	119.9	C42—C41—H41A	111.9
C14—C13—H13	119.9	O3—C41—H41B	111.9
O1—C14—C13	115.2 (3)	C42—C41—H41B	111.9
O1—C14—C15	124.4 (3)	H41A—C41—H41B	109.6
C13—C14—C15	120.4 (3)	C43—C42—C41	107.9 (6)
C16—C15—C14	118.7 (3)	C43—C42—H42A	110.1
C16—C15—H15	120.6	C41—C42—H42A	110.1
C14—C15—H15	120.6	C43—C42—H42B	110.1
C11—C16—C15	121.9 (3)	C41—C42—H42B	110.1
C11—C16—H16	119.1	H42A—C42—H42B	108.4
C15—C16—H16	119.1	Nⁱ—N—C1	117.2 (2)
O1—C17—H17A	109.5	Nⁱ—N—P	117.71 (19)
O1—C17—H17B	109.5	C1—N—P	123.29 (19)
H17A—C17—H17B	109.5	N—P—C11	102.49 (13)
O1—C17—H17C	109.5	N—P—C21	109.45 (13)
H17A—C17—H17C	109.5	C11—P—C21	104.82 (13)
H17B—C17—H17C	109.5	N—P—Au	111.57 (9)
C26—C21—C22	118.6 (3)	C11—P—Au	115.57 (9)
C26—C21—P	119.4 (2)	C21—P—Au	112.28 (10)
C22—C21—P	122.0 (2)	P—Au—Cl	175.98 (3)
C23—C22—C21	120.8 (3)	P—Au—Auⁱ	87.787 (19)
C23—C22—H22	119.6	Cl—Au—Auⁱ	95.61 (3)
C21—C22—H22	119.6	C14—O1—C17	117.4 (3)
C22—C23—C24	119.9 (3)	C24—O2—C27	117.1 (3)
C22—C23—H23	120.0	C44—C43—C42	110.0 (7)
C24—C23—H23	120.0	C44—C43—H43A	109.7
O2—C24—C23	114.9 (3)	C42—C43—H43A	109.7
O2—C24—C25	124.7 (3)	C44—C43—H43B	109.7
C23—C24—C25	120.3 (3)	C42—C43—H43B	109.7
C24—C25—C26	119.2 (3)	H43A—C43—H43B	108.2
C24—C25—H25	120.4

C16—C11—C12—C13	−1.8 (5)	Nⁱ—N—P—C11	−160.78 (18)
P—C11—C12—C13	173.0 (3)	C1—N—P—C11	35.1 (3)
C11—C12—C13—C14	0.2 (6)	Nⁱ—N—P—C21	88.37 (19)
C12—C13—C14—O1	−177.5 (4)	C1—N—P—C21	−75.8 (2)
C12—C13—C14—C15	2.3 (6)	Nⁱ—N—P—Au	−36.5 (2)
O1—C14—C15—C16	176.8 (3)	C1—N—P—Au	159.4 (2)
C13—C14—C15—C16	−3.0 (5)	C16—C11—P—N	79.6 (3)
C12—C11—C16—C15	1.1 (5)	C12—C11—P—N	−95.1 (3)
P—C11—C16—C15	−173.8 (3)	C16—C11—P—C21	−166.2 (2)
C14—C15—C16—C11	1.3 (5)	C12—C11—P—C21	19.2 (3)
C26—C21—C22—C23	0.3 (5)	C16—C11—P—Au	−42.0 (3)
P—C21—C22—C23	−179.1 (2)	C12—C11—P—Au	143.3 (2)
C21—C22—C23—C24	−1.5 (5)	C26—C21—P—N	−162.5 (2)
C22—C23—C24—O2	180.0 (3)	C22—C21—P—N	16.8 (3)
C22—C23—C24—C25	1.4 (5)	C26—C21—P—C11	88.2 (3)
O2—C24—C25—C26	−178.4 (3)	C22—C21—P—C11	−92.5 (3)
C23—C24—C25—C26	0.0 (5)	C26—C21—P—Au	−38.0 (3)
C22—C21—C26—C25	1.2 (5)	C22—C21—P—Au	141.3 (2)
P—C21—C26—C25	−179.5 (2)	C13—C14—O1—C17	169.4 (4)
C24—C25—C26—C21	−1.3 (5)	C15—C14—O1—C17	−10.4 (6)
C43—C44—O3—C41	5.1 (10)	C23—C24—O2—C27	179.9 (4)
C44—O3—C41—C42	−14.9 (7)	C25—C24—O2—C27	−1.5 (6)
O3—C41—C42—C43	20.2 (8)	O3—C44—C43—C42	9.3 (13)
C2—C1—N—Nⁱ	93.9 (3)	C41—C42—C43—C44	−18.8 (12)
C2—C1—N—P	−101.9 (3)

Symmetry code: (i) −x+2, y, −z+3/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1A···Clⁱⁱ	0.99	2.80	3.592 (3)	137
C13—H13···O1ⁱⁱⁱ	0.95	2.61	3.549 (4)	170
C15—H15···O3^iv	0.95	2.63	3.497 (5)	152
C17—H17B···O3^iv	0.98	2.53	3.444 (7)	156

Symmetry codes: (ii) −x+2, y−1, −z+3/2; (iii) −x+3/2, −y+1/2, −z+1; (iv) x, y+1, z.

Experimental details

Crystal data
Chemical formula	[Au₂Cl₂(C₃₂H₃₈N₂O₄P₂)]·2C₄H₈O
M_r	1185.63
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	173
a, b, c (Å)	23.6375 (4), 9.1260 (1), 20.2269 (3)
β (°)	93.976 (1)
V (Å³)	4352.76 (11)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	6.98
Crystal size (mm)	0.36 × 0.20 × 0.07

Data collection
Diffractometer	Bruker APEXII CCD
Absorption correction	Integration (SADABS; Bruker, 1999)
T_min, T_max	0.188, 0.641
No. of measured, independent and observed [I > 2σ(I)] reflections	38471, 5253, 4694
R_int	0.046
(sin θ/λ)_max (Å⁻¹)	0.661

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.022, 0.059, 1.05
No. of reflections	5253
No. of parameters	244
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.74, −0.64

Computer programs: APEX2 (Bruker, 1999), SAINT-Plus (Bruker, 1999), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), Mercury (Macrae et al., 2006), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1A···Clⁱ	0.99	2.80	3.592 (3)	137.2
C15—H15···O3ⁱⁱ	0.95	2.63	3.497 (5)	151.6
C17—H17B···O3ⁱⁱ	0.98	2.53	3.444 (7)	155.7

Symmetry codes: (i) −x+2, y−1, −z+3/2; (ii) x, y+1, z.

Acknowledgements

The authors would like to thank Project AuTEK (Mintek and Harmony) for financial support and the University of the Witwatersrand for the use of their facilities.

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