μ-Sulfido-bis{[1,1′-bis(diphenylphosphanyl)ferrocene-κ²P,P′]gold} methanol monosolvate

The gold complex in title compound, [Au₂Fe(C₁₇H₁₄P)₂S]·CH₃OH, (I)·CH₃OH, is closely similar to the previously reported (I)·2CHCl₃, reported in the literature [Canales et al. (1996). J. Am. Chem. Soc. 118, 4839–4845]. Both crystallize in the monoclinic crystal systems but the space groups differ, P2₁/n for (I)·CH₃OH compared to P2/n for (I)·2CHCl₃. The two structures can be considered as polymorphs due to solvation differences. In (I)·CH₃OH, all atoms of the methanol solvent mol­ecule are disordered over two sets of sites with an occupancy ratio of 0.822 (12):0.178 (12). The crystal structure features O—H...S, C—H...S hydrogen bonds and C—H...π inter­actions that stack the complex mol­ecules along the a-axis direction.

Key indicators

• Single-crystal X-ray study
• T = 200 K
• Mean [sigma](C-C) = 0.007 Å
• Disorder in solvent or counterion
• R factor = 0.031
• wR factor = 0.052
• Data-to-parameter ratio = 15.6

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT906_ALERT_3_C Large K value in the Analysis of Variance ......      4.828 Check
PLAT910_ALERT_3_C Missing # of FCF Reflection(s) Below Th(Min) ...         10 Report

Alert level G
PLAT003_ALERT_2_G Number of Uiso or Uij Restrained non-H Atoms ...          4 Report
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          2 Report
PLAT042_ALERT_1_G Calc. and Reported MoietyFormula Strings  Differ     Please Check
PLAT177_ALERT_4_G The CIF-Embedded .res File Contains DELU Records          2 Report
PLAT178_ALERT_4_G The CIF-Embedded .res File Contains SIMU Records          2 Report
PLAT302_ALERT_4_G Anion/Solvent Disorder ............ Percentage =        100 Note
PLAT304_ALERT_4_G Non-Integer Number of Atoms (   4.93) in Resd. #          2 Check
PLAT304_ALERT_4_G Non-Integer Number of Atoms (   1.07) in Resd. #          3 Check
PLAT860_ALERT_3_G Number of Least-Squares Restraints .............          8 Note

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   2 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   9 ALERT level G = General information/check it is not something unexpected

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   3 ALERT type 3 Indicator that the structure quality may be low
   5 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check

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S1. Synthesis and crystallization

To a solution of (1,1'-bis­(di­phenyl­phosphino)ferrocene)digold) (15.0 mg, 15.8 mmol) in 3 ml of methanol was added 20 µL (0.02 mmol) of an aqueous sodium hydrogen sulfide solution (1 M). The solution was allowed to stand at room temperature for 1 h when small qu­anti­ties of yellow needle-like crystals of [Au₂(C₃₄H₂₈FeP₂)(S)]·CH₃OH were obtained.

S2. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 1. A l l atoms of the methanol solvate molecules were disordered over two sites. Their occupancies were refined to sum to unity and converged at 0.822 (12) and 0.178 (12) respectively. Ten reflections below theta min = 3.227, with F_o <<< F_c were omitted as they were likely to have been obscured by the beamstop.

S3. Experimental

To a solution of {1,1'-bis[diphenylphosphino)ferrocene]digold} (15.0 mg, 15.8 mmol) in 3 ml of methanol was added 20 µL (0.02 mmol) of an aqueous sodium hydrogen sulfide solution (1 M). The solution was allowed to stand at room temperature for 1 h when small quantities of yellow needle-like crystals of [Au₂(C₃₄H₂₈FeP₂)(S)]·CH₃OH were obtained.

S4. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 3. A l l atoms of the methanol solvate molecules were disordered over two sets ofsites. Their occupancies were refined to sum to unity and converged at 0.822 (12) and 0.178 (12) respectively. Ten reflections below θ_min = 3.227, with F_o <<< F_c were omitted as they were likely to have been obscured by the beamstop.

Structure description

The asymmetric unit in the title crystal structure contains one [Au₂(dppf)(S)] complex molecule, (I)·CH₃OH, dppf = 1,1'-bis(diphenylphosphino)ferrocene) and a methanol solvate molecule, all atoms of which are disordered over two sets of sites with a 0.822 (12):0.178 (12) occupancy ratio, Fig. 1. Both Au^I cations adopt a slightly distorted linear coordination geometry, each binding separate P atoms from the dppf ligand and bridged by the sulfido anion, leading to a close intramolecular Au—Au contact of 2.8857 (3) Å, similar to that observed in the closely related (I)·2CHCl₃ (Canales et al., 1996). The Au—S and Au—P distances, Table 1, are also similar to those in the earlier report. Although the space groups of these two structures differ, P2₁/n for (I)·CH₃OH and P2/n for (I)·2CHCl₃. The two structures can be considered as pseudopolymorphs due to solvation differences which will significantly affect the crystal packing. Apart from the psudopolymorph, only two examples of digoldsufide systems similarly bridged by bidentate diphenylphosphino ligands, (µ₂-2,5-bis(diphenylphosphinomethyl)thiophene)(µ₂-sulfido)digold(I) (Chen et al., 1998) and {µ₂-1,4-bis[(diphenylphosphino)methyl]benzene}(µ₂-sulfido)digold(I) chloroform solvate (Hofreiter et al., 1995) are found in the Cambridge Structural Database, (Groom & Allen, 2014).

In the crystal structure, an O—H···S hydrogen bond links the major disorder component of the methanol molecule to the complex molecule in the asymmetric unit, Table 2. A C—H···S hydrogen bond and two edge-to-face C—H···π contacts link adjacent complex molecules, stacking them along the a-axis direction, Fig. 2. For the psudopolymorphic structure, which lies about a twofold rotation axis, C—H···S and C—H···Cl hydrogen bonds, a weaker C—H···π contact and an intermolecular Cl···Cl halogen bond stabilize the structure.

Computing details

Data collection: PROCESS-AUTO (Rigaku, 2000); cell refinement: PROCESS-AUTO (Rigaku, 2000); data reduction: PROCESS-AUTO (Rigaku, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: DIAMOND (Putz & Brandenburg, 2011); software used to prepare material for publication: WinGX (Farrugia, 2012).

Figures

	Fig. 1. The molecular structure of the title compound with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level and H atoms are drawn as spheres of arbitrary radii.
	Fig. 2. Overall packing for the title compound viewed along the a axis.

µ-Sulfido-bis{[1,1'-bis(diphenylphosphanyl)ferrocene-κP,P']gold} methanol monosolvate

Crystal data

[Au2Fe(C17H14P)2S]·CH4O	F(000) = 1920
Mr = 1012.39	Dx = 2.087 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71075 Å
a = 13.7434 (13) Å	Cell parameters from 8771 reflections
b = 12.6277 (13) Å	θ = 3.0–27.5°
c = 18.7630 (18) Å	µ = 9.72 mm^−1
β = 98.352 (7)°	T = 200 K
V = 3221.7 (5) Å^3	Needle, yellow
Z = 4	0.30 × 0.10 × 0.01 mm

Data collection

Rigaku VariMax RAPID diffractometer	5445 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.045
ω scans	θmax = 25.7°, θmin = 3.2°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −16→16
Tmin = 0.572, Tmax = 0.995	k = −15→15
26469 measured reflections	l = −22→22
6105 independent reflections

Refinement

Refinement on F^2	8 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.031	H-atom parameters constrained
wR(F^2) = 0.052	w = 1/[σ^2(Fo^2) + (0.0208P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.13	(Δ/σ)max = 0.001
6105 reflections	Δρmax = 1.03 e Å^−3
392 parameters	Δρmin = −0.55 e Å^−3

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
Au1	0.39803 (2)	0.23503 (2)	0.09507 (2)	0.02544 (6)
Au2	0.23078 (2)	0.20488 (2)	0.16975 (2)	0.02555 (6)
Fe1	0.47576 (5)	0.32726 (5)	0.31861 (3)	0.02381 (15)
P1	0.54820 (9)	0.27998 (9)	0.15170 (6)	0.0231 (3)
P2	0.23049 (9)	0.25682 (9)	0.28416 (6)	0.0235 (3)
S1	0.24432 (9)	0.17001 (10)	0.05135 (6)	0.0315 (3)
C1	0.5572 (3)	0.2623 (3)	0.2479 (2)	0.0226 (10)
C2	0.6197 (3)	0.3142 (4)	0.3044 (2)	0.0274 (10)
H2	0.6635	0.3708	0.2989	0.033*
C3	0.6049 (4)	0.2665 (4)	0.3704 (3)	0.0308 (11)
H3	0.6367	0.2859	0.4170	0.037*
C4	0.5348 (3)	0.1852 (4)	0.3546 (3)	0.0320 (11)
H4	0.5112	0.1404	0.3890	0.038*
C5	0.5054 (3)	0.1814 (3)	0.2799 (2)	0.0260 (10)
H5	0.4592	0.1334	0.2550	0.031*
C6	0.5925 (3)	0.4134 (3)	0.1388 (2)	0.0265 (10)
C7	0.5275 (4)	0.4882 (4)	0.1072 (3)	0.0432 (14)
H7	0.4600	0.4709	0.0944	0.052*
C8	0.5609 (5)	0.5893 (4)	0.0940 (4)	0.0604 (18)
H8	0.5159	0.6404	0.0713	0.073*
C9	0.6571 (5)	0.6162 (4)	0.1131 (3)	0.0498 (15)
H9	0.6789	0.6857	0.1043	0.060*
C10	0.7220 (4)	0.5426 (4)	0.1448 (3)	0.0403 (13)
H10	0.7891	0.5613	0.1586	0.048*
C11	0.6908 (3)	0.4405 (4)	0.1572 (2)	0.0321 (11)
H11	0.7368	0.3892	0.1783	0.038*
C12	0.6439 (3)	0.1923 (3)	0.1277 (2)	0.0246 (10)
C13	0.7252 (3)	0.1646 (4)	0.1775 (3)	0.0316 (11)
H13	0.7322	0.1926	0.2249	0.038*
C14	0.7960 (4)	0.0964 (4)	0.1582 (3)	0.0402 (13)
H14	0.8520	0.0788	0.1921	0.048*
C15	0.7848 (4)	0.0543 (4)	0.0900 (3)	0.0408 (13)
H15	0.8333	0.0075	0.0767	0.049*
C16	0.7043 (4)	0.0793 (4)	0.0407 (3)	0.0423 (14)
H16	0.6968	0.0492	−0.0061	0.051*
C17	0.6335 (4)	0.1488 (3)	0.0594 (2)	0.0311 (11)
H17	0.5779	0.1664	0.0251	0.037*
C18	0.3279 (3)	0.3494 (3)	0.3119 (2)	0.0254 (10)
C19	0.3748 (3)	0.3704 (4)	0.3834 (3)	0.0334 (12)
H19	0.3623	0.3349	0.4257	0.040*
C20	0.4427 (3)	0.4529 (4)	0.3803 (3)	0.0439 (15)
H20	0.4843	0.4826	0.4201	0.053*
C21	0.4383 (4)	0.4837 (4)	0.3079 (3)	0.0419 (14)
H21	0.4763	0.5384	0.2907	0.050*
C22	0.3681 (3)	0.4201 (3)	0.2646 (3)	0.0320 (12)
H22	0.3511	0.4239	0.2138	0.038*
C23	0.2466 (3)	0.1536 (3)	0.3525 (2)	0.0254 (10)
C24	0.2985 (3)	0.0625 (4)	0.3396 (3)	0.0324 (11)
H24	0.3234	0.0548	0.2952	0.039*
C25	0.3141 (4)	−0.0162 (4)	0.3903 (3)	0.0410 (13)
H25	0.3494	−0.0781	0.3809	0.049*
C26	0.2785 (4)	−0.0056 (4)	0.4547 (3)	0.0459 (14)
H26	0.2897	−0.0602	0.4898	0.055*
C27	0.2269 (4)	0.0834 (4)	0.4687 (3)	0.0483 (15)
H27	0.2020	0.0904	0.5131	0.058*
C28	0.2115 (4)	0.1625 (4)	0.4175 (3)	0.0363 (12)
H28	0.1761	0.2242	0.4272	0.044*
C29	0.1186 (3)	0.3250 (3)	0.2995 (2)	0.0241 (10)
C30	0.1185 (4)	0.4138 (4)	0.3427 (3)	0.0321 (11)
H30	0.1791	0.4446	0.3634	0.038*
C31	0.0309 (4)	0.4580 (4)	0.3558 (3)	0.0408 (13)
H31	0.0318	0.5182	0.3863	0.049*
C32	−0.0563 (4)	0.4163 (4)	0.3254 (3)	0.0508 (16)
H32	−0.1162	0.4474	0.3345	0.061*
C33	−0.0578 (4)	0.3285 (4)	0.2812 (4)	0.065 (2)
H33	−0.1189	0.2990	0.2602	0.077*
C34	0.0291 (4)	0.2838 (4)	0.2676 (3)	0.0499 (16)
H34	0.0278	0.2245	0.2364	0.060*
O1	−0.0057 (4)	0.1917 (5)	0.0573 (5)	0.095 (3)	0.822 (12)
H1A	0.0554	0.1950	0.0574	0.143*	0.822 (12)
C35	−0.0431 (17)	0.2927 (15)	0.0602 (13)	0.113 (7)	0.822 (12)
H35A	−0.0284	0.3335	0.0187	0.170*	0.822 (12)
H35B	−0.0131	0.3273	0.1048	0.170*	0.822 (12)
H35C	−0.1145	0.2889	0.0593	0.170*	0.822 (12)
O2	0.025 (2)	0.292 (2)	0.0241 (16)	0.074 (11)*	0.178 (12)
H2B	0.0519	0.3513	0.0309	0.111*	0.178 (12)
C36	−0.042 (4)	0.284 (4)	0.063 (3)	0.024 (11)*	0.178 (12)
H36A	−0.0388	0.3442	0.0962	0.037*	0.178 (12)
H36B	−0.0333	0.2179	0.0908	0.037*	0.178 (12)
H36C	−0.1065	0.2830	0.0326	0.037*	0.178 (12)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Au1	0.02336 (10)	0.03084 (10)	0.02091 (10)	0.00051 (8)	−0.00083 (7)	−0.00180 (7)
Au2	0.02393 (10)	0.02795 (10)	0.02366 (10)	−0.00089 (8)	−0.00025 (7)	−0.00423 (7)
Fe1	0.0194 (3)	0.0265 (3)	0.0249 (4)	0.0004 (3)	0.0013 (3)	−0.0051 (3)
P1	0.0212 (6)	0.0264 (6)	0.0210 (6)	0.0000 (5)	0.0008 (5)	−0.0009 (5)
P2	0.0200 (6)	0.0252 (6)	0.0250 (6)	−0.0006 (5)	0.0024 (5)	−0.0031 (5)
S1	0.0268 (7)	0.0415 (7)	0.0235 (6)	−0.0007 (6)	−0.0051 (5)	−0.0083 (5)
C1	0.019 (2)	0.027 (2)	0.023 (2)	0.002 (2)	0.0030 (19)	−0.0018 (19)
C2	0.017 (2)	0.037 (3)	0.027 (3)	0.001 (2)	−0.002 (2)	−0.004 (2)
C3	0.025 (3)	0.044 (3)	0.021 (3)	0.007 (2)	−0.002 (2)	−0.005 (2)
C4	0.034 (3)	0.037 (3)	0.025 (3)	0.009 (2)	0.005 (2)	0.003 (2)
C5	0.026 (3)	0.026 (2)	0.025 (3)	0.002 (2)	0.004 (2)	−0.0005 (19)
C6	0.031 (3)	0.028 (2)	0.022 (3)	0.000 (2)	0.007 (2)	−0.0012 (19)
C7	0.040 (3)	0.037 (3)	0.052 (4)	−0.004 (3)	0.004 (3)	0.008 (3)
C8	0.062 (5)	0.033 (3)	0.085 (5)	−0.002 (3)	0.006 (4)	0.015 (3)
C9	0.066 (4)	0.026 (3)	0.059 (4)	−0.014 (3)	0.014 (3)	0.005 (3)
C10	0.041 (3)	0.045 (3)	0.035 (3)	−0.017 (3)	0.008 (3)	−0.008 (2)
C11	0.027 (3)	0.039 (3)	0.030 (3)	−0.003 (2)	0.005 (2)	−0.001 (2)
C12	0.022 (2)	0.026 (2)	0.029 (3)	−0.001 (2)	0.011 (2)	−0.0021 (19)
C13	0.026 (3)	0.035 (3)	0.033 (3)	−0.001 (2)	0.004 (2)	−0.003 (2)
C14	0.024 (3)	0.041 (3)	0.056 (4)	0.005 (2)	0.004 (3)	−0.001 (3)
C15	0.034 (3)	0.039 (3)	0.053 (4)	0.008 (3)	0.019 (3)	−0.004 (3)
C16	0.057 (4)	0.039 (3)	0.035 (3)	0.007 (3)	0.020 (3)	−0.001 (2)
C17	0.033 (3)	0.036 (3)	0.025 (3)	0.003 (2)	0.006 (2)	0.000 (2)
C18	0.019 (2)	0.029 (2)	0.028 (3)	0.004 (2)	0.002 (2)	−0.011 (2)
C19	0.025 (3)	0.045 (3)	0.031 (3)	0.003 (2)	0.006 (2)	−0.017 (2)
C20	0.020 (3)	0.046 (3)	0.065 (4)	−0.001 (2)	0.001 (3)	−0.035 (3)
C21	0.024 (3)	0.023 (2)	0.078 (5)	−0.001 (2)	0.006 (3)	−0.005 (3)
C22	0.017 (3)	0.027 (2)	0.052 (3)	0.004 (2)	0.006 (2)	0.005 (2)
C23	0.023 (2)	0.027 (2)	0.027 (3)	−0.004 (2)	0.004 (2)	−0.0046 (19)
C24	0.029 (3)	0.032 (3)	0.035 (3)	−0.002 (2)	0.005 (2)	−0.003 (2)
C25	0.043 (3)	0.026 (3)	0.052 (4)	0.002 (2)	0.000 (3)	0.001 (2)
C26	0.048 (4)	0.039 (3)	0.046 (4)	−0.004 (3)	−0.006 (3)	0.013 (3)
C27	0.054 (4)	0.058 (3)	0.034 (3)	−0.001 (3)	0.011 (3)	0.008 (3)
C28	0.039 (3)	0.038 (3)	0.033 (3)	0.007 (2)	0.011 (2)	−0.002 (2)
C29	0.019 (2)	0.026 (2)	0.026 (3)	−0.001 (2)	−0.0004 (19)	0.0022 (19)
C30	0.025 (3)	0.034 (3)	0.037 (3)	−0.001 (2)	0.003 (2)	−0.006 (2)
C31	0.034 (3)	0.032 (3)	0.057 (4)	0.004 (2)	0.011 (3)	−0.012 (2)
C32	0.027 (3)	0.040 (3)	0.087 (5)	0.008 (3)	0.013 (3)	−0.004 (3)
C33	0.023 (3)	0.047 (3)	0.117 (6)	0.002 (3)	−0.012 (3)	−0.024 (4)
C34	0.029 (3)	0.037 (3)	0.079 (5)	0.001 (3)	−0.008 (3)	−0.023 (3)
O1	0.038 (4)	0.083 (5)	0.159 (8)	−0.005 (3)	−0.009 (4)	0.015 (4)
C35	0.090 (10)	0.089 (9)	0.155 (16)	−0.001 (7)	0.001 (9)	0.010 (8)

Geometric parameters (Å, º)

Au1—P1	2.2524 (12)	C15—C16	1.372 (7)
Au1—S1	2.3036 (12)	C15—H15	0.9500
Au2—P2	2.2452 (12)	C16—C17	1.392 (6)
Au2—S1	2.2988 (12)	C16—H16	0.9500
Au1—Au2	2.8857 (3)	C17—H17	0.9500
Fe1—C1	2.029 (4)	C18—C19	1.425 (6)
Fe1—C18	2.037 (4)	C18—C22	1.426 (6)
Fe1—C22	2.038 (5)	C19—C20	1.406 (7)
Fe1—C2	2.041 (4)	C19—H19	0.9500
Fe1—C4	2.042 (5)	C20—C21	1.405 (7)
Fe1—C5	2.043 (4)	C20—H20	0.9500
Fe1—C21	2.044 (5)	C21—C22	1.416 (7)
Fe1—C3	2.046 (5)	C21—H21	0.9500
Fe1—C19	2.047 (4)	C22—H22	0.9500
Fe1—C20	2.053 (5)	C23—C28	1.379 (6)
P1—C1	1.805 (4)	C23—C24	1.393 (6)
P1—C6	1.819 (4)	C24—C25	1.371 (7)
P1—C12	1.825 (4)	C24—H24	0.9500
P2—C18	1.797 (4)	C25—C26	1.374 (7)
P2—C23	1.820 (5)	C25—H25	0.9500
P2—C29	1.822 (4)	C26—C27	1.375 (7)
C1—C2	1.423 (6)	C26—H26	0.9500
C1—C5	1.427 (6)	C27—C28	1.381 (7)
C2—C3	1.418 (6)	C27—H27	0.9500
C2—H2	0.9500	C28—H28	0.9500
C3—C4	1.410 (7)	C29—C30	1.383 (6)
C3—H3	0.9500	C29—C34	1.388 (7)
C4—C5	1.401 (6)	C30—C31	1.381 (6)
C4—H4	0.9500	C30—H30	0.9500
C5—H5	0.9500	C31—C32	1.356 (7)
C6—C7	1.373 (6)	C31—H31	0.9500
C6—C11	1.389 (6)	C32—C33	1.383 (7)
C7—C8	1.392 (7)	C32—H32	0.9500
C7—H7	0.9500	C33—C34	1.378 (7)
C8—C9	1.362 (8)	C33—H33	0.9500
C8—H8	0.9500	C34—H34	0.9500
C9—C10	1.364 (7)	O1—C35	1.378 (18)
C9—H9	0.9500	O1—H1A	0.8400
C10—C11	1.389 (6)	C35—H35A	0.9800
C10—H10	0.9500	C35—H35B	0.9800
C11—H11	0.9500	C35—H35C	0.9800
C12—C17	1.383 (6)	O2—C36	1.26 (6)
C12—C13	1.393 (6)	O2—H2B	0.8400
C13—C14	1.386 (6)	C36—H36A	0.9800
C13—H13	0.9500	C36—H36B	0.9800
C14—C15	1.375 (7)	C36—H36C	0.9800
C14—H14	0.9500
S1—Au1—Au2	51.10 (3)	C10—C9—H9	120.2
S1—Au2—Au1	51.24 (3)	C9—C10—C11	120.5 (5)
P1—Au1—S1	171.06 (4)	C9—C10—H10	119.8
P2—Au2—S1	172.59 (4)	C11—C10—H10	119.8
P1—Au1—Au2	122.96 (3)	C10—C11—C6	120.0 (5)
P2—Au2—Au1	122.54 (3)	C10—C11—H11	120.0
C1—Fe1—C18	130.97 (18)	C6—C11—H11	120.0
C1—Fe1—C22	109.71 (19)	C17—C12—C13	119.1 (4)
C18—Fe1—C22	40.97 (17)	C17—C12—P1	119.2 (4)
C1—Fe1—C2	40.94 (17)	C13—C12—P1	121.6 (3)
C18—Fe1—C2	168.62 (18)	C14—C13—C12	120.5 (5)
C22—Fe1—C2	128.96 (18)	C14—C13—H13	119.8
C1—Fe1—C4	68.34 (17)	C12—C13—H13	119.8
C18—Fe1—C4	119.05 (18)	C15—C14—C13	119.7 (5)
C22—Fe1—C4	153.41 (19)	C15—C14—H14	120.2
C2—Fe1—C4	68.08 (18)	C13—C14—H14	120.2
C1—Fe1—C5	41.03 (16)	C16—C15—C14	120.6 (5)
C18—Fe1—C5	110.54 (18)	C16—C15—H15	119.7
C22—Fe1—C5	120.68 (19)	C14—C15—H15	119.7
C2—Fe1—C5	68.50 (18)	C15—C16—C17	120.1 (5)
C4—Fe1—C5	40.12 (18)	C15—C16—H16	119.9
C1—Fe1—C21	118.8 (2)	C17—C16—H16	119.9
C18—Fe1—C21	68.06 (18)	C12—C17—C16	120.0 (5)
C22—Fe1—C21	40.60 (19)	C12—C17—H17	120.0
C2—Fe1—C21	107.47 (19)	C16—C17—H17	120.0
C4—Fe1—C21	164.5 (2)	C19—C18—C22	107.8 (4)
C5—Fe1—C21	153.8 (2)	C19—C18—P2	127.6 (4)
C1—Fe1—C3	68.64 (18)	C22—C18—P2	124.5 (4)
C18—Fe1—C3	150.45 (19)	C19—C18—Fe1	69.9 (2)
C22—Fe1—C3	165.73 (18)	C22—C18—Fe1	69.5 (2)
C2—Fe1—C3	40.62 (18)	P2—C18—Fe1	128.5 (2)
C4—Fe1—C3	40.36 (19)	C20—C19—C18	108.1 (5)
C5—Fe1—C3	68.06 (19)	C20—C19—Fe1	70.2 (3)
C21—Fe1—C3	126.7 (2)	C18—C19—Fe1	69.2 (2)
C1—Fe1—C19	169.06 (18)	C20—C19—H19	125.9
C18—Fe1—C19	40.85 (18)	C18—C19—H19	125.9
C22—Fe1—C19	68.7 (2)	Fe1—C19—H19	126.3
C2—Fe1—C19	148.51 (19)	C21—C20—C19	108.0 (5)
C4—Fe1—C19	108.0 (2)	C21—C20—Fe1	69.6 (3)
C5—Fe1—C19	129.69 (19)	C19—C20—Fe1	69.7 (3)
C21—Fe1—C19	67.6 (2)	C21—C20—H20	126.0
C3—Fe1—C19	115.7 (2)	C19—C20—H20	126.0
C1—Fe1—C20	150.34 (19)	Fe1—C20—H20	126.3
C18—Fe1—C20	68.17 (18)	C20—C21—C22	109.1 (4)
C22—Fe1—C20	68.4 (2)	C20—C21—Fe1	70.3 (3)
C2—Fe1—C20	115.72 (19)	C22—C21—Fe1	69.5 (2)
C4—Fe1—C20	127.0 (2)	C20—C21—H21	125.4
C5—Fe1—C20	165.7 (2)	C22—C21—H21	125.4
C21—Fe1—C20	40.1 (2)	Fe1—C21—H21	126.4
C3—Fe1—C20	105.7 (2)	C21—C22—C18	106.9 (5)
C19—Fe1—C20	40.10 (18)	C21—C22—Fe1	69.9 (3)
C1—P1—C6	105.8 (2)	C18—C22—Fe1	69.5 (3)
C1—P1—C12	103.0 (2)	C21—C22—H22	126.5
C6—P1—C12	105.18 (19)	C18—C22—H22	126.5
C1—P1—Au1	111.46 (15)	Fe1—C22—H22	125.6
C6—P1—Au1	118.15 (16)	C28—C23—C24	118.4 (4)
C12—P1—Au1	112.01 (16)	C28—C23—P2	122.8 (3)
C18—P2—C23	104.6 (2)	C24—C23—P2	118.8 (3)
C18—P2—C29	104.90 (19)	C25—C24—C23	120.7 (4)
C23—P2—C29	104.3 (2)	C25—C24—H24	119.7
C18—P2—Au2	111.26 (15)	C23—C24—H24	119.7
C23—P2—Au2	116.60 (14)	C24—C25—C26	120.0 (5)
C29—P2—Au2	114.08 (15)	C24—C25—H25	120.0
Au2—S1—Au1	77.66 (4)	C26—C25—H25	120.0
C2—C1—C5	107.5 (4)	C25—C26—C27	120.4 (5)
C2—C1—P1	129.4 (3)	C25—C26—H26	119.8
C5—C1—P1	122.9 (3)	C27—C26—H26	119.8
C2—C1—Fe1	70.0 (2)	C26—C27—C28	119.3 (5)
C5—C1—Fe1	70.0 (2)	C26—C27—H27	120.3
P1—C1—Fe1	129.7 (2)	C28—C27—H27	120.3
C3—C2—C1	107.9 (4)	C23—C28—C27	121.2 (5)
C3—C2—Fe1	69.9 (3)	C23—C28—H28	119.4
C1—C2—Fe1	69.1 (2)	C27—C28—H28	119.4
C3—C2—H2	126.0	C30—C29—C34	118.7 (4)
C1—C2—H2	126.0	C30—C29—P2	123.2 (4)
Fe1—C2—H2	126.5	C34—C29—P2	118.0 (4)
C4—C3—C2	107.8 (4)	C31—C30—C29	120.5 (5)
C4—C3—Fe1	69.7 (3)	C31—C30—H30	119.8
C2—C3—Fe1	69.5 (3)	C29—C30—H30	119.8
C4—C3—H3	126.1	C32—C31—C30	120.5 (5)
C2—C3—H3	126.1	C32—C31—H31	119.7
Fe1—C3—H3	126.3	C30—C31—H31	119.7
C5—C4—C3	108.9 (4)	C31—C32—C33	119.9 (5)
C5—C4—Fe1	69.9 (3)	C31—C32—H32	120.1
C3—C4—Fe1	69.9 (3)	C33—C32—H32	120.1
C5—C4—H4	125.5	C34—C33—C32	120.1 (5)
C3—C4—H4	125.5	C34—C33—H33	119.9
Fe1—C4—H4	126.2	C32—C33—H33	119.9
C4—C5—C1	107.9 (4)	C33—C34—C29	120.3 (5)
C4—C5—Fe1	69.9 (3)	C33—C34—H34	119.9
C1—C5—Fe1	69.0 (2)	C29—C34—H34	119.9
C4—C5—H5	126.0	C35—O1—H1A	109.5
C1—C5—H5	126.0	O1—C35—H35A	109.5
Fe1—C5—H5	126.6	O1—C35—H35B	109.5
C7—C6—C11	119.1 (4)	H35A—C35—H35B	109.5
C7—C6—P1	119.0 (4)	O1—C35—H35C	109.5
C11—C6—P1	121.8 (4)	H35A—C35—H35C	109.5
C6—C7—C8	119.9 (5)	H35B—C35—H35C	109.5
C6—C7—H7	120.1	C36—O2—H2B	109.5
C8—C7—H7	120.1	O2—C36—H36A	109.5
C9—C8—C7	120.9 (6)	O2—C36—H36B	109.5
C9—C8—H8	119.5	H36A—C36—H36B	109.5
C7—C8—H8	119.5	O2—C36—H36C	109.5
C8—C9—C10	119.6 (5)	H36A—C36—H36C	109.5
C8—C9—H9	120.2	H36B—C36—H36C	109.5
C6—P1—C1—C2	−24.5 (5)	C23—P2—C18—C19	−28.2 (4)
C12—P1—C1—C2	85.6 (4)	C29—P2—C18—C19	81.2 (4)
Au1—P1—C1—C2	−154.1 (4)	Au2—P2—C18—C19	−154.9 (3)
C6—P1—C1—C5	162.0 (4)	C23—P2—C18—C22	155.5 (3)
C12—P1—C1—C5	−87.9 (4)	C29—P2—C18—C22	−95.0 (4)
Au1—P1—C1—C5	32.4 (4)	Au2—P2—C18—C22	28.8 (4)
C6—P1—C1—Fe1	71.6 (3)	C23—P2—C18—Fe1	65.2 (3)
C12—P1—C1—Fe1	−178.3 (3)	C29—P2—C18—Fe1	174.7 (3)
Au1—P1—C1—Fe1	−58.1 (3)	Au2—P2—C18—Fe1	−61.5 (3)
C5—C1—C2—C3	−0.9 (5)	C22—C18—C19—C20	0.1 (5)
P1—C1—C2—C3	−175.2 (3)	P2—C18—C19—C20	−176.6 (3)
Fe1—C1—C2—C3	59.3 (3)	Fe1—C18—C19—C20	59.6 (3)
C5—C1—C2—Fe1	−60.2 (3)	C22—C18—C19—Fe1	−59.5 (3)
P1—C1—C2—Fe1	125.5 (4)	P2—C18—C19—Fe1	123.8 (3)
C1—C2—C3—C4	0.6 (5)	C18—C19—C20—C21	0.3 (5)
Fe1—C2—C3—C4	59.4 (3)	Fe1—C19—C20—C21	59.3 (3)
C1—C2—C3—Fe1	−58.8 (3)	C18—C19—C20—Fe1	−59.0 (3)
C2—C3—C4—C5	0.0 (5)	C19—C20—C21—C22	−0.6 (5)
Fe1—C3—C4—C5	59.3 (3)	Fe1—C20—C21—C22	58.8 (3)
C2—C3—C4—Fe1	−59.3 (3)	C19—C20—C21—Fe1	−59.4 (3)
C3—C4—C5—C1	−0.5 (5)	C20—C21—C22—C18	0.6 (5)
Fe1—C4—C5—C1	58.7 (3)	Fe1—C21—C22—C18	59.9 (3)
C3—C4—C5—Fe1	−59.3 (3)	C20—C21—C22—Fe1	−59.3 (3)
C2—C1—C5—C4	0.9 (5)	C19—C18—C22—C21	−0.5 (5)
P1—C1—C5—C4	175.6 (3)	P2—C18—C22—C21	176.4 (3)
Fe1—C1—C5—C4	−59.3 (3)	Fe1—C18—C22—C21	−60.2 (3)
C2—C1—C5—Fe1	60.2 (3)	C19—C18—C22—Fe1	59.7 (3)
P1—C1—C5—Fe1	−125.1 (3)	P2—C18—C22—Fe1	−123.4 (3)
C1—P1—C6—C7	−113.1 (4)	C18—P2—C23—C28	82.6 (4)
C12—P1—C6—C7	138.3 (4)	C29—P2—C23—C28	−27.3 (5)
Au1—P1—C6—C7	12.5 (4)	Au2—P2—C23—C28	−154.0 (4)
C1—P1—C6—C11	69.6 (4)	C18—P2—C23—C24	−95.9 (4)
C12—P1—C6—C11	−38.9 (4)	C29—P2—C23—C24	154.2 (4)
Au1—P1—C6—C11	−164.8 (3)	Au2—P2—C23—C24	27.4 (4)
C11—C6—C7—C8	0.2 (8)	C28—C23—C24—C25	0.0 (7)
P1—C6—C7—C8	−177.2 (4)	P2—C23—C24—C25	178.7 (4)
C6—C7—C8—C9	−1.2 (9)	C23—C24—C25—C26	−0.1 (8)
C7—C8—C9—C10	0.8 (10)	C24—C25—C26—C27	0.3 (9)
C8—C9—C10—C11	0.5 (9)	C25—C26—C27—C28	−0.4 (9)
C9—C10—C11—C6	−1.5 (7)	C24—C23—C28—C27	−0.1 (8)
C7—C6—C11—C10	1.2 (7)	P2—C23—C28—C27	−178.7 (4)
P1—C6—C11—C10	178.4 (3)	C26—C27—C28—C23	0.3 (9)
C1—P1—C12—C17	152.1 (3)	C18—P2—C29—C30	−16.6 (4)
C6—P1—C12—C17	−97.4 (4)	C23—P2—C29—C30	93.1 (4)
Au1—P1—C12—C17	32.2 (4)	Au2—P2—C29—C30	−138.6 (4)
C1—P1—C12—C13	−25.2 (4)	C18—P2—C29—C34	165.1 (4)
C6—P1—C12—C13	85.4 (4)	C23—P2—C29—C34	−85.2 (4)
Au1—P1—C12—C13	−145.1 (3)	Au2—P2—C29—C34	43.1 (4)
C17—C12—C13—C14	1.6 (7)	C34—C29—C30—C31	2.3 (7)
P1—C12—C13—C14	178.9 (4)	P2—C29—C30—C31	−176.0 (4)
C12—C13—C14—C15	−1.3 (7)	C29—C30—C31—C32	−1.3 (8)
C13—C14—C15—C16	0.1 (8)	C30—C31—C32—C33	0.3 (9)
C14—C15—C16—C17	0.7 (8)	C31—C32—C33—C34	−0.4 (10)
C13—C12—C17—C16	−0.8 (7)	C32—C33—C34—C29	1.5 (10)
P1—C12—C17—C16	−178.1 (3)	C30—C29—C34—C33	−2.4 (8)
C15—C16—C17—C12	−0.4 (7)	P2—C29—C34—C33	175.9 (5)

Hydrogen-bond geometry (Å, º)

Cg1 and Cg2 are the centroids of the C7–C11 and C12–C16 phenyl rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···S1	0.84	2.63	3.465 (6)	170
C3—H3···S1^i	0.95	2.79	3.734 (5)	175
C27—H27···Cg(1)^ii	0.95	2.83	3.659 (6)	146
C32—H32···Cg(2)^iii	0.95	2.88	3.717 (6)	147

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