{μ-2-[1-(N,N-Dimethyl­amino)eth­yl]ferrocene-1,1′-diylbis(diphenyl­phosphine)-κ2P:P′}bis­[chloro­gold(I)]

Sam, Z.A.; Oskarsson, A.; Elmroth, S.K.C.; Roodt, A.

doi:10.1107/S1600536805029582

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{μ-2-[1-(N,N-Dimethylamino)ethyl]ferrocene-1,1′-diylbis(diphenylphosphine)-κ²P:P′}bis[chlorogold(I)]

Z. A. Sam, A. Oskarsson, S. K. C. Elmroth and A. Roodt

The structure of the title compound, [Au₂Fe(C₂₁H₂₃NP)(C₁₇H₁₄P)Cl₂], displays the pseudo-linear [P–Au–Cl = 175.4 (1) and 174.0 (1)°] two-coordinate geometry usually observed in gold(I) complexes. The Au—P bond distances are 2.237 (2) and 2.224 (2) Å and the Au—Cl distances are 2.271 (3) and 2.278 (2) Å. The bis(diphenylphosphino)ferrocenyl ligand links the gold metal centres in a bidentate fashion via the ferrocene group, thus leading to a binuclear gold system.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805029582/xu6048sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536805029582/xu6048Isup2.hkl Contains datablock I

CCDC reference: 287762

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.015 Å
R factor = 0.049
wR factor = 0.109
Data-to-parameter ratio = 19.3

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature .        293 K
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.70 Ratio
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C55
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        Au1
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         N1
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C51
PLAT331_ALERT_2_C Small Average Phenyl C-C Dist.   C51    -C56           1.36 Ang.
PLAT342_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...         15

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   9 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   6 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion

Comment top

Research towards the synthesis and reactivity of the transition metal complexes with ferrocene-bridged bis(tertiary phosphine) ligands such as 1,1'-bis(diphenylphosphino)ferrocene (dppf) has been increasingly interesting (Bruce et al., 1990, Hor et al., 1992). The use of these ferrocenylphosphines as ligands in coordination chemistry has enlarged the scope of metal complexes in the design of catalysts (Togni & Pastor, 1990), drugs (Hill et al., 1989; Houlton et al., 1991) and materials (Hayashi et al., 1980). Catalytic reactions found in literature include the gold(I)-catalysed aldol reactions of enolates with aldehydes to give optically active β-hydroxycarbonyl compounds (Ito et al., 1986, 1987). Several chiral phosphine ligands have been employed in catalytic asymmetric reactions yielding high enantioselectivity. An example is the effect observed in the rhodium-catalysed asymmetric hydrogenation of α-(acylamino)acrylic acids and/or their analogues leading to the hydrogenation products of over 90% ee (Morrison, 1985). However, few of them displayed this high enantioselectivity in other types of catalytic asymmetric reactions (Noyori & Takaya, 1990, and references therein). Reported in this paper is a modified bis(diphenylphosphino)ferrocenyl gold(I) analogue, (I), which has a ethylamine group specifically designed for improved solubility of the gold complex.

The compound is a Au^I complex comprising a diphenylphosphine ferrocenyl ligand bearing phosphorus and nitrogen coordination sites. As gold is a soft metal, it preferentially coordinates to the P atom, the soft coordination site in the ferrocenyl ligand. Since there are two of these sites in the complex, gold coordinates to each site and hence leads to a binuclear gold system, as shown in Fig. 1.

The coordination mode of the diphenylphosphine is of an open-bridging fashion, with the direction of displacement of P atom from coplanarity with cyclopentadienyl ring. The angle involving the two P atoms in the system (P—Fe—P) is 165.97 (7)°, and the cyclopentadienyl rings are partially eclipsed anticlinical relative to each other. The phenyl groups in the system are twisted slightly perpendicular to each other, with a (C_ar—P—C_ar)_av of 104.6 (4)°. The coordination around the gold atoms is pseudo-linear (Table 1). The Au—P and Au—Cl bond distances are within the normal range compared with (diphenylphosphino)ferrocenyl complexes found in literature (Hill et al., 1989; Crespo et al., 2000; Canales et al., 1997). For comparison, selected bond distances and angles for other similar Au^I complexes are presented in Table 3.

The packing of the molecules in the unit cell is illustrated in Fig. 2. The molecules orientate so the centre of the Fe atom lies directly on the c axis. The molecule was also investigated for possible π–π interactions, but did not show any significant effects. However, weak intermolecular C—H···Cl hydrogen bonding is observed (Table 2).

Experimental top

The title compound was prepared according to a procedure similar to one described earlier by Gimeno et al. (1993). A solution of [(THT)AuCl] (THT = tetrahydrothiophene) (0.092 g, 0.3 mmol) in dichloromethane (30 ml) was treated with dppf-CH(CH₃)N(CH₃)₂ (Bjelosevic et al., 2005) (0.094 g, 0.15 mmol) and the mixture was stirred for 30 min. The solution was concentrated to approximately 10 ml and addition of diethyl ether (25 ml) gave the desired product (0.15 g, 92%). ¹H NMR (CDCl₃, 300 MHz): δ 0.81 (d, 3H, CHCH₃), 1.52 (s, 6H, NCH₃), 3.74–4.91 (m, 8H), 7.34–7.74 (m, 20H, PC₆H₅) ³¹P{¹H} NMR (CDCl₃, 121.5 MHz): δ 26.963 (s), 28.68 (s) IR (KBr, ν, cm⁻¹): 692 (s), 750 (m), 1023 (w), 1100 (m), 1434 (s), 1480 (m)

Computing details top

Data collection: Please supply; cell refinement: SAINT-Plus (Bruker, 1999); data reduction: SAINT-Plus and XPREP (Bruker, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: DIAMOND (Brandenburg & Berndt, 2001); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

	Fig. 1. The molecular structure of (I), with displacement ellipsoids drawn at the 30% probability level. H atoms have been omitted for clarity.
	Fig. 2. Packing diagram of (I). H atoms have been omitted for clarity.

{µ-2-[1-(N,N-Dimethylamino)ethyl]ferrocene-1,1'-diylbis(diphenylphosphine)- κ²P:P'}bis[chlorogold(I)] top

Crystal data top

[Au₂Fe(C₂₁H₂₃NP)(C₁₇H₁₄P)Cl₂]	F(000) = 2080
M_r = 1090.31	D_x = 1.97 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 824 reflections
a = 17.136 (3) Å	θ = 2.2–21.3°
b = 10.946 (2) Å	µ = 8.61 mm⁻¹
c = 20.658 (4) Å	T = 293 K
β = 108.39 (3)°	Needles, orange
V = 3676.7 (13) Å³	0.17 × 0.05 × 0.03 mm
Z = 4

Data collection top

Bruker SMART CCD diffractometer	8020 independent reflections
Radiation source: fine-focus sealed tube	4488 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.098
ω scans	θ_max = 27.0°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 1998)	h = −21→18
T_min = 0.600, T_max = 0.772	k = −13→13
30273 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)] = 0.049	H-atom parameters constrained
wR(F²) = 0.109	w = 1/[σ²(F_o²) + (0.044P)²] where P = (F_o² + 2F_c²)/3
S = 0.99	(Δ/σ)_max = 0.001
8020 reflections	Δρ_max = 2.10 e Å⁻³
415 parameters	Δρ_min = −1.15 e Å⁻³
0 restraints

Crystal data top

[Au₂Fe(C₂₁H₂₃NP)(C₁₇H₁₄P)Cl₂]	V = 3676.7 (13) Å³
M_r = 1090.31	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 17.136 (3) Å	µ = 8.61 mm⁻¹
b = 10.946 (2) Å	T = 293 K
c = 20.658 (4) Å	0.17 × 0.05 × 0.03 mm
β = 108.39 (3)°

Data collection top

Bruker SMART CCD diffractometer	8020 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 1998)	4488 reflections with I > 2σ(I)
T_min = 0.600, T_max = 0.772	R_int = 0.098
30273 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.049	0 restraints
wR(F²) = 0.109	H-atom parameters constrained
S = 0.99	Δρ_max = 2.10 e Å⁻³
8020 reflections	Δρ_min = −1.15 e Å⁻³
415 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
Au1	0.07005 (2)	0.35943 (3)	0.28527 (2)	0.04780 (13)
Au2	−0.12000 (2)	−0.35119 (3)	0.127362 (18)	0.04006 (12)
Fe	0.00262 (8)	−0.00152 (10)	0.20019 (6)	0.0378 (3)
P1	0.15261 (14)	0.20977 (19)	0.27198 (12)	0.0356 (6)
P2	−0.17475 (14)	−0.17948 (19)	0.15122 (12)	0.0352 (6)
N1	0.1206 (5)	0.1108 (7)	0.4088 (4)	0.049 (2)
Cl1	−0.0061 (2)	0.5148 (3)	0.30690 (18)	0.1114 (14)
Cl2	−0.07468 (18)	−0.5271 (2)	0.09230 (15)	0.0650 (8)
C11	0.2501 (5)	0.2132 (8)	0.3413 (4)	0.039 (2)
C12	0.2700 (6)	0.3173 (8)	0.3815 (4)	0.045 (2)
H12	0.2331	0.3822	0.3735	0.054*
C13	0.3437 (7)	0.3250 (9)	0.4331 (5)	0.063 (3)
H13	0.3569	0.3945	0.4602	0.075*
C14	0.3975 (7)	0.2291 (11)	0.4439 (5)	0.071 (3)
H14	0.4484	0.2355	0.4775	0.085*
C15	0.3782 (7)	0.1256 (10)	0.4069 (6)	0.070 (4)
H15	0.4149	0.0604	0.4161	0.084*
C16	0.3039 (6)	0.1164 (8)	0.3554 (5)	0.049 (3)
H16	0.2903	0.0446	0.3302	0.059*
C21	0.1802 (6)	0.2267 (8)	0.1933 (4)	0.039 (2)
C22	0.2515 (6)	0.1742 (9)	0.1860 (5)	0.054 (3)
H22	0.2884	0.1333	0.2224	0.065*
C23	0.2662 (7)	0.1836 (10)	0.1245 (6)	0.064 (3)
H23	0.3132	0.1482	0.1193	0.077*
C24	0.2117 (8)	0.2452 (10)	0.0703 (6)	0.067 (3)
H24	0.2228	0.2516	0.0292	0.08*
C25	0.1412 (8)	0.2972 (10)	0.0768 (5)	0.069 (3)
H25	0.1037	0.3358	0.0398	0.083*
C26	0.1274 (6)	0.2912 (8)	0.1383 (5)	0.051 (3)
H26	0.0818	0.3309	0.1438	0.061*
C31	0.1130 (5)	0.0554 (7)	0.2656 (4)	0.033 (2)
C32	0.1253 (6)	−0.0367 (8)	0.2201 (5)	0.047 (2)
H32	0.155	−0.0274	0.1897	0.056*
C33	0.0837 (6)	−0.1451 (8)	0.2299 (5)	0.052 (3)
H33	0.081	−0.2188	0.2069	0.062*
C34	0.0477 (6)	−0.1192 (7)	0.2810 (5)	0.041 (2)
H34	0.0176	−0.1745	0.2978	0.049*
C35	0.0640 (5)	0.0038 (7)	0.3031 (4)	0.037 (2)
C36	0.0416 (5)	0.0694 (8)	0.3590 (4)	0.040 (2)
H36	0.0101	0.1425	0.3389	0.048*
C37	−0.0124 (6)	−0.0080 (10)	0.3886 (5)	0.069 (3)
H37A	−0.0256	0.0371	0.4236	0.104*
H37B	0.0164	−0.0814	0.4077	0.104*
H37C	−0.0622	−0.0288	0.3531	0.104*
C38	0.1743 (7)	0.0133 (11)	0.4451 (6)	0.084 (4)
H38A	0.1807	−0.0462	0.413	0.126*
H38B	0.1505	−0.025	0.4763	0.126*
H38C	0.2271	0.0465	0.47	0.126*
C39	0.1085 (7)	0.2036 (10)	0.4549 (6)	0.079 (4)
H39A	0.0728	0.2662	0.4291	0.118*
H39B	0.1606	0.2388	0.4799	0.118*
H39C	0.084	0.1672	0.4861	0.118*
C41	−0.1160 (5)	−0.0468 (7)	0.1476 (4)	0.038 (2)
C42	−0.1124 (6)	0.0710 (8)	0.1799 (5)	0.051 (3)
H42	−0.1371	0.0922	0.2124	0.062*
C43	−0.0647 (6)	0.1473 (9)	0.1531 (6)	0.066 (4)
H43	−0.054	0.2292	0.1644	0.079*
C44	−0.0355 (7)	0.0839 (10)	0.1070 (5)	0.065 (3)
H44	−0.002	0.1152	0.0833	0.079*
C45	−0.0661 (6)	−0.0373 (9)	0.1029 (5)	0.050 (3)
H45	−0.0559	−0.0997	0.0761	0.06*
C51	−0.2739 (5)	−0.1520 (8)	0.0864 (5)	0.040 (2)
C52	−0.2901 (6)	−0.0496 (9)	0.0471 (6)	0.068 (3)
H52	−0.2507	0.0116	0.0539	0.082*
C53	−0.3637 (7)	−0.0371 (11)	−0.0020 (6)	0.079 (4)
H53	−0.3729	0.0325	−0.0291	0.095*
C54	−0.4242 (6)	−0.1201 (11)	−0.0134 (6)	0.071 (3)
H54	−0.4753	−0.1072	−0.0458	0.085*
C55	−0.4071 (7)	−0.2247 (12)	0.0249 (7)	0.089 (4)
H55	−0.4465	−0.2862	0.0166	0.107*
C56	−0.3334 (6)	−0.2410 (10)	0.0751 (5)	0.067 (3)
H56	−0.3237	−0.3117	0.1014	0.08*
C61	−0.1986 (5)	−0.1766 (7)	0.2315 (4)	0.037 (2)
C62	−0.2569 (6)	−0.0997 (10)	0.2389 (5)	0.062 (3)
H62	−0.2838	−0.047	0.2036	0.074*
C63	−0.2771 (7)	−0.0987 (11)	0.2990 (7)	0.075 (4)
H63	−0.3168	−0.045	0.3039	0.09*
C64	−0.2380 (7)	−0.1775 (11)	0.3512 (6)	0.070 (3)
H64	−0.2506	−0.1772	0.3918	0.084*
C65	−0.1803 (7)	−0.2561 (9)	0.3421 (5)	0.058 (3)
H65	−0.1541	−0.3101	0.3769	0.07*
C66	−0.1602 (6)	−0.2572 (8)	0.2826 (5)	0.044 (2)
H66	−0.1211	−0.3118	0.2771	0.053*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Au1	0.0454 (2)	0.0383 (2)	0.0513 (3)	0.01094 (18)	0.00322 (19)	−0.00698 (19)
Au2	0.0450 (2)	0.03126 (19)	0.0473 (2)	0.00300 (17)	0.01926 (18)	−0.00059 (17)
Fe	0.0380 (7)	0.0298 (6)	0.0394 (8)	−0.0020 (6)	0.0035 (6)	0.0016 (6)
P1	0.0311 (13)	0.0302 (12)	0.0412 (15)	0.0003 (10)	0.0055 (11)	−0.0003 (10)
P2	0.0365 (13)	0.0271 (11)	0.0404 (14)	−0.0002 (10)	0.0098 (11)	−0.0020 (10)
N1	0.052 (5)	0.053 (5)	0.041 (5)	−0.004 (4)	0.014 (4)	−0.007 (4)
Cl1	0.101 (3)	0.105 (3)	0.097 (3)	0.065 (2)	−0.013 (2)	−0.042 (2)
Cl2	0.081 (2)	0.0431 (14)	0.081 (2)	0.0124 (14)	0.0397 (17)	−0.0070 (13)
C11	0.041 (5)	0.035 (5)	0.039 (6)	−0.001 (4)	0.009 (4)	0.009 (4)
C12	0.053 (6)	0.044 (5)	0.036 (6)	−0.005 (5)	0.013 (5)	−0.003 (4)
C13	0.066 (8)	0.056 (7)	0.052 (7)	−0.013 (6)	−0.001 (6)	−0.008 (5)
C14	0.055 (7)	0.080 (9)	0.052 (8)	−0.008 (7)	−0.018 (6)	0.008 (6)
C15	0.059 (7)	0.063 (8)	0.069 (8)	0.007 (6)	−0.007 (6)	0.024 (6)
C16	0.042 (6)	0.038 (5)	0.059 (7)	−0.004 (4)	0.004 (5)	0.004 (5)
C21	0.047 (6)	0.035 (5)	0.033 (5)	−0.012 (4)	0.010 (4)	0.000 (4)
C22	0.052 (7)	0.061 (7)	0.048 (7)	−0.007 (5)	0.013 (5)	−0.009 (5)
C23	0.071 (8)	0.072 (8)	0.065 (8)	−0.007 (6)	0.042 (7)	−0.015 (6)
C24	0.094 (10)	0.061 (7)	0.061 (8)	−0.030 (7)	0.046 (8)	−0.013 (6)
C25	0.104 (10)	0.065 (7)	0.039 (7)	−0.022 (8)	0.024 (7)	0.008 (6)
C26	0.063 (7)	0.034 (5)	0.051 (7)	−0.011 (5)	0.011 (5)	−0.001 (5)
C31	0.022 (5)	0.038 (5)	0.035 (5)	0.005 (4)	0.004 (4)	−0.001 (4)
C32	0.046 (6)	0.044 (6)	0.054 (7)	0.001 (5)	0.021 (5)	−0.017 (5)
C33	0.048 (6)	0.041 (5)	0.058 (7)	0.002 (5)	0.004 (5)	−0.009 (5)
C34	0.040 (5)	0.028 (5)	0.044 (6)	0.000 (4)	−0.003 (5)	0.010 (4)
C35	0.036 (5)	0.027 (5)	0.042 (6)	0.009 (4)	0.006 (4)	0.002 (4)
C36	0.040 (5)	0.037 (5)	0.044 (6)	−0.004 (4)	0.014 (5)	0.002 (4)
C37	0.061 (7)	0.096 (9)	0.055 (7)	−0.025 (7)	0.025 (6)	−0.014 (6)
C38	0.068 (8)	0.100 (10)	0.068 (9)	0.014 (7)	−0.002 (7)	0.000 (7)
C39	0.088 (9)	0.082 (8)	0.066 (8)	−0.024 (7)	0.022 (7)	−0.034 (7)
C41	0.036 (5)	0.032 (5)	0.037 (6)	−0.003 (4)	−0.003 (4)	0.000 (4)
C42	0.047 (6)	0.044 (6)	0.044 (6)	0.010 (5)	−0.013 (5)	−0.007 (5)
C43	0.055 (7)	0.033 (5)	0.080 (9)	−0.013 (5)	−0.021 (6)	0.022 (6)
C44	0.082 (9)	0.068 (8)	0.033 (6)	−0.017 (7)	−0.002 (6)	0.018 (6)
C45	0.059 (7)	0.054 (6)	0.031 (6)	−0.017 (5)	0.004 (5)	−0.003 (5)
C51	0.040 (5)	0.036 (5)	0.046 (6)	−0.004 (5)	0.014 (4)	0.000 (5)
C52	0.055 (7)	0.045 (6)	0.082 (9)	0.002 (5)	−0.010 (6)	−0.005 (6)
C53	0.068 (9)	0.083 (9)	0.068 (9)	−0.002 (7)	−0.005 (7)	0.019 (7)
C54	0.037 (6)	0.088 (9)	0.070 (8)	0.008 (6)	−0.007 (6)	0.005 (7)
C55	0.053 (8)	0.092 (10)	0.096 (11)	−0.004 (7)	−0.012 (7)	0.011 (8)
C56	0.058 (7)	0.061 (7)	0.065 (8)	−0.017 (6)	−0.006 (6)	0.012 (6)
C61	0.033 (5)	0.034 (5)	0.038 (5)	0.004 (4)	0.002 (4)	0.006 (4)
C62	0.061 (7)	0.081 (8)	0.044 (7)	0.036 (6)	0.018 (6)	0.006 (6)
C63	0.064 (8)	0.076 (8)	0.092 (10)	0.020 (7)	0.037 (8)	−0.005 (7)
C64	0.078 (9)	0.096 (9)	0.043 (7)	−0.004 (7)	0.028 (6)	−0.015 (6)
C65	0.067 (8)	0.061 (7)	0.038 (7)	−0.011 (6)	0.004 (5)	0.012 (5)
C66	0.045 (6)	0.042 (5)	0.044 (6)	0.003 (5)	0.011 (5)	0.001 (5)

Geometric parameters (Å, º) top

Au1—P1	2.237 (2)	C32—H32	0.93
Au1—Cl1	2.271 (3)	C33—C34	1.411 (13)
Au2—P2	2.224 (2)	C33—H33	0.93
Au2—Cl2	2.278 (2)	C34—C35	1.421 (11)
Fe—C45	2.022 (9)	C34—H34	0.93
Fe—C41	2.041 (8)	C35—C36	1.508 (12)
Fe—C42	2.042 (9)	C36—C37	1.518 (12)
Fe—C31	2.045 (8)	C36—H36	0.98
Fe—C32	2.047 (9)	C37—H37A	0.96
Fe—C44	2.052 (9)	C37—H37B	0.96
Fe—C35	2.054 (8)	C37—H37C	0.96
Fe—C43	2.055 (9)	C38—H38A	0.96
Fe—C34	2.057 (8)	C38—H38B	0.96
Fe—C33	2.059 (9)	C38—H38C	0.96
P1—C31	1.810 (9)	C39—H39A	0.96
P1—C11	1.825 (9)	C39—H39B	0.96
P1—C21	1.839 (9)	C39—H39C	0.96
P2—C41	1.781 (9)	C41—C42	1.444 (12)
P2—C51	1.826 (9)	C41—C45	1.447 (13)
P2—C61	1.828 (9)	C42—C43	1.399 (14)
N1—C39	1.451 (12)	C42—H42	0.93
N1—C38	1.454 (12)	C43—C44	1.392 (15)
N1—C36	1.489 (11)	C43—H43	0.93
C11—C16	1.374 (12)	C44—C45	1.419 (13)
C11—C12	1.388 (11)	C44—H44	0.93
C12—C13	1.375 (13)	C45—H45	0.93
C12—H12	0.93	C51—C52	1.359 (12)
C13—C14	1.367 (14)	C51—C56	1.377 (12)
C13—H13	0.93	C52—C53	1.353 (14)
C14—C15	1.348 (14)	C52—H52	0.93
C14—H14	0.93	C53—C54	1.342 (14)
C15—C16	1.382 (13)	C53—H53	0.93
C15—H15	0.93	C54—C55	1.369 (15)
C16—H16	0.93	C54—H54	0.93
C21—C26	1.400 (12)	C55—C56	1.370 (14)
C21—C22	1.401 (12)	C55—H55	0.93
C22—C23	1.375 (13)	C56—H56	0.93
C22—H22	0.93	C61—C62	1.353 (12)
C23—C24	1.386 (15)	C61—C66	1.374 (11)
C23—H23	0.93	C62—C63	1.388 (14)
C24—C25	1.380 (15)	C62—H62	0.93
C24—H24	0.93	C63—C64	1.379 (15)
C25—C26	1.366 (13)	C63—H63	0.93
C25—H25	0.93	C64—C65	1.367 (14)
C26—H26	0.93	C64—H64	0.93
C31—C35	1.428 (12)	C65—C66	1.378 (13)
C31—C32	1.438 (11)	C65—H65	0.93
C32—C33	1.431 (12)	C66—H66	0.93

P1—Au1—Cl1	175.4 (1)	Fe—C32—H32	126.1
P2—Au2—Cl2	174.0 (1)	C34—C33—C32	107.1 (8)
C45—Fe—C41	41.7 (4)	C34—C33—Fe	69.8 (5)
C45—Fe—C42	69.5 (4)	C32—C33—Fe	69.1 (5)
C41—Fe—C42	41.4 (3)	C34—C33—H33	126.5
C45—Fe—C31	147.5 (4)	C32—C33—H33	126.5
C41—Fe—C31	169.9 (3)	Fe—C33—H33	126.1
C42—Fe—C31	130.5 (3)	C33—C34—C35	110.1 (9)
C45—Fe—C32	113.7 (4)	C33—C34—Fe	70.1 (5)
C41—Fe—C32	148.0 (3)	C35—C34—Fe	69.7 (5)
C42—Fe—C32	167.9 (4)	C33—C34—H34	125
C31—Fe—C32	41.1 (3)	C35—C34—H34	125
C45—Fe—C44	40.8 (4)	Fe—C34—H34	126.9
C41—Fe—C44	69.1 (4)	C34—C35—C31	106.8 (8)
C42—Fe—C44	68.2 (5)	C34—C35—C36	128.7 (9)
C31—Fe—C44	115.8 (4)	C31—C35—C36	124.3 (7)
C32—Fe—C44	106.0 (5)	C34—C35—Fe	69.9 (5)
C45—Fe—C35	169.1 (3)	C31—C35—Fe	69.2 (5)
C41—Fe—C35	131.0 (4)	C36—C35—Fe	129.4 (6)
C42—Fe—C35	110.3 (4)	N1—C36—C35	106.1 (7)
C31—Fe—C35	40.8 (3)	N1—C36—C37	115.4 (8)
C32—Fe—C35	68.9 (4)	C35—C36—C37	112.1 (8)
C44—Fe—C35	149.9 (4)	N1—C36—H36	107.6
C45—Fe—C43	67.6 (4)	C35—C36—H36	107.6
C41—Fe—C43	67.9 (3)	C37—C36—H36	107.6
C42—Fe—C43	39.9 (4)	C36—C37—H37A	109.5
C31—Fe—C43	109.6 (4)	C36—C37—H37B	109.5
C32—Fe—C43	129.2 (4)	H37A—C37—H37B	109.5
C44—Fe—C43	39.6 (4)	C36—C37—H37C	109.5
C35—Fe—C43	119.7 (4)	H37A—C37—H37C	109.5
C45—Fe—C34	129.6 (4)	H37B—C37—H37C	109.5
C41—Fe—C34	109.6 (4)	N1—C38—H38A	109.5
C42—Fe—C34	120.1 (4)	N1—C38—H38B	109.5
C31—Fe—C34	67.8 (3)	H38A—C38—H38B	109.5
C32—Fe—C34	67.7 (4)	N1—C38—H38C	109.5
C44—Fe—C34	166.8 (4)	H38A—C38—H38C	109.5
C35—Fe—C34	40.4 (3)	H38B—C38—H38C	109.5
C43—Fe—C34	153.1 (5)	N1—C39—H39A	109.5
C45—Fe—C33	106.0 (4)	N1—C39—H39B	109.5
C41—Fe—C33	116.0 (3)	H39A—C39—H39B	109.5
C42—Fe—C33	151.0 (4)	N1—C39—H39C	109.5
C31—Fe—C33	68.8 (3)	H39A—C39—H39C	109.5
C32—Fe—C33	40.8 (3)	H39B—C39—H39C	109.5
C44—Fe—C33	127.7 (5)	C42—C41—C45	106.4 (8)
C35—Fe—C33	68.7 (3)	C42—C41—P2	130.6 (8)
C43—Fe—C33	166.3 (5)	C45—C41—P2	122.8 (7)
C34—Fe—C33	40.1 (4)	C42—C41—Fe	69.3 (5)
C31—P1—C11	107.8 (4)	C45—C41—Fe	68.4 (5)
C31—P1—C21	102.9 (4)	P2—C41—Fe	131.0 (5)
C11—P1—C21	105.3 (4)	C43—C42—C41	107.2 (10)
C31—P1—Au1	117.1 (3)	C43—C42—Fe	70.6 (6)
C11—P1—Au1	110.3 (3)	C41—C42—Fe	69.3 (5)
C21—P1—Au1	112.5 (3)	C43—C42—H42	126.4
C41—P2—C51	104.0 (4)	C41—C42—H42	126.4
C41—P2—C61	108.3 (4)	Fe—C42—H42	125.4
C51—P2—C61	103.9 (4)	C44—C43—C42	110.7 (9)
C41—P2—Au2	113.3 (3)	C44—C43—Fe	70.1 (6)
C51—P2—Au2	109.7 (3)	C42—C43—Fe	69.5 (5)
C61—P2—Au2	116.5 (3)	C44—C43—H43	124.6
C39—N1—C38	112.0 (9)	C42—C43—H43	124.6
C39—N1—C36	112.3 (8)	Fe—C43—H43	127.4
C38—N1—C36	115.0 (8)	C43—C44—C45	107.5 (10)
C16—C11—C12	119.0 (8)	C43—C44—Fe	70.3 (6)
C16—C11—P1	122.5 (7)	C45—C44—Fe	68.5 (5)
C12—C11—P1	118.5 (7)	C43—C44—H44	126.2
C13—C12—C11	120.4 (9)	C45—C44—H44	126.2
C13—C12—H12	119.8	Fe—C44—H44	126.5
C11—C12—H12	119.8	C44—C45—C41	108.1 (9)
C14—C13—C12	119.1 (10)	C44—C45—Fe	70.8 (5)
C14—C13—H13	120.4	C41—C45—Fe	69.9 (5)
C12—C13—H13	120.4	C44—C45—H45	125.9
C15—C14—C13	121.4 (10)	C41—C45—H45	125.9
C15—C14—H14	119.3	Fe—C45—H45	125
C13—C14—H14	119.3	C52—C51—C56	118.8 (9)
C14—C15—C16	120.0 (10)	C52—C51—P2	122.8 (7)
C14—C15—H15	120	C56—C51—P2	118.4 (7)
C16—C15—H15	120	C53—C52—C51	119.8 (10)
C11—C16—C15	120.0 (9)	C53—C52—H52	120.1
C11—C16—H16	120	C51—C52—H52	120.1
C15—C16—H16	120	C54—C53—C52	123.3 (11)
C26—C21—C22	118.8 (9)	C54—C53—H53	118.3
C26—C21—P1	119.2 (8)	C52—C53—H53	118.3
C22—C21—P1	122.0 (7)	C53—C54—C55	116.9 (10)
C23—C22—C21	119.4 (10)	C53—C54—H54	121.6
C23—C22—H22	120.3	C55—C54—H54	121.6
C21—C22—H22	120.3	C54—C55—C56	121.6 (11)
C22—C23—C24	120.6 (11)	C54—C55—H55	119.2
C22—C23—H23	119.7	C56—C55—H55	119.2
C24—C23—H23	119.7	C55—C56—C51	119.5 (10)
C25—C24—C23	120.7 (10)	C55—C56—H56	120.2
C25—C24—H24	119.7	C51—C56—H56	120.2
C23—C24—H24	119.7	C62—C61—C66	120.3 (9)
C26—C25—C24	119.0 (11)	C62—C61—P2	119.9 (7)
C26—C25—H25	120.5	C66—C61—P2	119.7 (7)
C24—C25—H25	120.5	C61—C62—C63	120.5 (10)
C25—C26—C21	121.5 (11)	C61—C62—H62	119.8
C25—C26—H26	119.3	C63—C62—H62	119.8
C21—C26—H26	119.3	C64—C63—C62	119.9 (10)
C35—C31—C32	108.1 (7)	C64—C63—H63	120.1
C35—C31—P1	126.9 (6)	C62—C63—H63	120.1
C32—C31—P1	125.0 (7)	C65—C64—C63	118.7 (10)
C35—C31—Fe	70.0 (5)	C65—C64—H64	120.7
C32—C31—Fe	69.5 (5)	C63—C64—H64	120.7
P1—C31—Fe	125.4 (4)	C64—C65—C66	121.6 (10)
C33—C32—C31	107.9 (8)	C64—C65—H65	119.2
C33—C32—Fe	70.1 (5)	C66—C65—H65	119.2
C31—C32—Fe	69.3 (5)	C61—C66—C65	119.1 (9)
C33—C32—H32	126.1	C61—C66—H66	120.5
C31—C32—H32	126.1	C65—C66—H66	120.5

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C66—H66···Cl1ⁱ	0.93	2.67	3.552 (10)	160

Symmetry code: (i) x, y−1, z.

Experimental details

Crystal data
Chemical formula	[Au₂Fe(C₂₁H₂₃NP)(C₁₇H₁₄P)Cl₂]
M_r	1090.31
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	293
a, b, c (Å)	17.136 (3), 10.946 (2), 20.658 (4)
β (°)	108.39 (3)
V (Å³)	3676.7 (13)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	8.61
Crystal size (mm)	0.17 × 0.05 × 0.03

Data collection
Diffractometer	Bruker SMART CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 1998)
T_min, T_max	0.600, 0.772
No. of measured, independent and observed [I > 2σ(I)] reflections	30273, 8020, 4488
R_int	0.098
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.049, 0.109, 0.99
No. of reflections	8020
No. of parameters	415
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	2.10, −1.15

Computer programs: Please supply, SAINT-Plus (Bruker, 1999), SAINT-Plus and XPREP (Bruker, 1999), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), DIAMOND (Brandenburg & Berndt, 2001), WinGX (Farrugia, 1999).

Selected geometric parameters (Å, º) top

Au1—P1	2.237 (2)	P1—C11	1.825 (9)
Au1—Cl1	2.271 (3)	P1—C21	1.839 (9)
Au2—P2	2.224 (2)	P2—C41	1.781 (9)
Au2—Cl2	2.278 (2)	P2—C51	1.826 (9)
P1—C31	1.810 (9)	P2—C61	1.828 (9)

P1—Au1—Cl1	175.4 (1)	C31—P1—Au1	117.1 (3)
P2—Au2—Cl2	174.0 (1)	C51—P2—C61	103.9 (4)
C11—P1—C21	105.3 (4)	C41—P2—Au2	113.3 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C66—H66···Cl1ⁱ	0.930	2.67	3.552 (10)	160

Symmetry code: (i) x, y−1, z.

Comparative geometrical parameters (Å, °) for selected gold(I) ferrocenyl complexes top

Complex	Au–P	Au–Cl	P–Au–Cl
[(dppf-R)(AuCl)₂]^a	2.237 (2)	2.271 (3)	175.4 (1)
	2.224 (2)	2.278 (2)	174.0 (1)
[(dppf)(AuCl)₂]^b	2.2262 (13)	2.2815 (13)	179.59 (5)
[(dppf)(AuCl₂]^c	2.239 (3)	2.300 (3)	176.0 (1)
	2.222 (3)	2.273 (4)	175.5 (1)
[(dppf)(AuCl)₂]^d	2.226 (1)	2.278 (1)	177.56 (8)
[(C₂₇H₂₈FeNP)(AuCl)]^e	2.24 (1)	2.32 (1)	176.5 (5)
[(dppf-L)₂(AuCl)₃]^f	2.31 (2)	2.52 (3)	113 (2)
	2.28 (2)	2.20 (2)	177 (2)

Notes: (a) this work, R = –CH(CH₃)N(CH₃)₂, dppf is 1,1'-bis(diphenylphosphino)ferrocene; (b) Canales et al. (1997), isolated as the CH₂Cl₂ solvate; (c) Hill et al. (1989), isolated as the CH₃Cl solvate; (d) Canales et al. (1997); (e) Viotte et al. (1996), isolated as the C₆H₆ 1.5-solvate, C₂₇H₂₈FeNP = (α-dimethylamino[3]ferrocenophanyl)diphenylphosphine; (f) Togni et al. (1990), L = –CH(CH₃)N(CH₃)CH₂CH₂N(CH₃)₂, isolated as the Et₂O solvate.

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