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Acta Crystallogr Sect E Struct Rep Online. 2009 December 1; 65(Pt 12): m1597.
Published online 2009 November 18. doi:  10.1107/S1600536809047898
PMCID: PMC2971759

[μ-1,1′-Bis(diphenyl­phosphino)ferrocene-κ2 P:P′]bis­{[(Z)-O-isopropyl-N-(4-methyl­phen­yl)thio­carbamato-κS]gold(I)}

Abstract

In the title compound, [Au2Fe(C11H14NOS)2(C17H14P)2], the FeII atom is located on a crystallographic centre of inversion. For the AuI atom, the deviation from linearity defined by its S,P-donor set [S—Au—P = 178.17 (8) Å] is due to an intra­molecular Au(...)O contact [3.079 (4) Å]. In the crystal, supra­molecular chains mediated by C—H(...)N inter­actions are formed, which run parallel to [001].

Related literature

For structural systematics and luminescence properties of phosphinegold(I) carbonimidothio­ates, see: Ho et al. (2006 [triangle]); Ho & Tiekink (2007 [triangle]); Kuan et al. (2008 [triangle]). For the synthesis, see Hall et al. (1993 [triangle]). For a related structure, see Ho & Tiekink (2009 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-m1597-scheme1.jpg

Experimental

Crystal data

  • [Au2Fe(C11H14NOS)2(C17H14P)2]
  • M r = 1364.87
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-m1597-efi1.jpg
  • a = 8.1631 (9) Å
  • b = 13.4959 (14) Å
  • c = 13.5154 (14) Å
  • α = 107.440 (2)°
  • β = 97.401 (2)°
  • γ = 106.366 (2)°
  • V = 1325.5 (2) Å3
  • Z = 1
  • Mo Kα radiation
  • μ = 5.97 mm−1
  • T = 223 K
  • 0.21 × 0.07 × 0.04 mm

Data collection

  • Bruker SMART CCD diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2000 [triangle]) T min = 0.629, T max = 1
  • 7710 measured reflections
  • 4651 independent reflections
  • 3790 reflections with I > 2σ(I)
  • R int = 0.036

Refinement

  • R[F 2 > 2σ(F 2)] = 0.040
  • wR(F 2) = 0.088
  • S = 0.98
  • 4651 reflections
  • 305 parameters
  • H-atom parameters constrained
  • Δρmax = 1.74 e Å−3
  • Δρmin = −0.93 e Å−3

Data collection: SMART (Bruker, 2000 [triangle]); cell refinement: SAINT (Bruker, 2000 [triangle]); data reduction: SAINT; program(s) used to solve structure: PATTY in DIRDIF92 (Beurskens et al., 1992 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: DIAMOND (Brandenburg, 2006 [triangle]); software used to prepare material for publication: publCIF (Westrip, 2009 [triangle]).

Table 1
Selected bond lengths (Å)
Table 2
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809047898/hb5221sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809047898/hb5221Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

The National University of Singapore (grant No. R-143–000–213–112) is thanked for support.

supplementary crystallographic information

Comment

As a part of systematic studies of phosphinegold(I) thiocarbamides (Ho et al. 2006; Ho & Tiekink, 2007; Kuan et al., 2008), the title compound, dppf{Au[SC(O-iPr)NC6H4Me-p]}2, was synthesized, (I); dppf is (Ph2PC5H4)2Fe. The dinuclear molecule has crystallographic symmetry with the Fe atom lying on an inversion centre, Fig. 1.

The gold atom exists in the expected linear geometry defined by a SP donor set, Table 1, and the deviation from linearity [S1–Au–P1 is 178.17 (8) Å] is ascribed to the close approach of the O1 atom, Au···O = 3.079 (4) Å. The anion, with a Z configuration about the C1═N1 bond, shows the expected characteristics. The magnitudes of C1—S1 and C1═N1 of 1.753 (7) and 1.253 (9) Å, respectively, confirm that the anion is coordinating as a thiolate. The overall conformation of the molecule is "open" in that the thiocarbamate ligands are lying on either side of the molecule. This contrasts the situation in each of dppf{Au[SC(OR)NC6H4NO2-p]}2, for R = Me (Ho et al., 2006) and iPr (Ho & Tiekink, 2009), whereby the molecule has a U-shaped conformation allowing for the formation of intramolecular Au···Au interactions.

In the crystal structure of (I), supramolecular chains are formed down the c axis owing to the presence of C–H···N interactions, Table 2 and Fig. 2.

Experimental

Compound (I) was prepared following the standard literature procedure from the reaction of dppf(AuCl)2 and (iPr)OC(S)N(H)C6H4Me-p in the presence of base (Hall et al., 1993).

Refinement

The H atoms were geometrically placed (C—H = 0.94–0.99 Å) and refined as riding with Uiso(H) = 1.2–1.5Ueq(C). The maximum and minimum residual electron density peaks of 1.74 and 0.93 e Å-3, respectively, were located 1.03 Å and 1.02 Å from the Au atom.

Figures

Fig. 1.
Molecular structure of the dinuclear complex (I) showing displacement ellipsoids at the 50% probability level. The molecule is located about a centre of inversion and unlabelled atoms are related by the symmetry operation 1 - x, 1 - y, -z.
Fig. 2.
Supramolecular chain in (I) mediated by C—H···N contacts (blue dashed lines). Colour code: Au, orange; S, yellow; P, pink; O, red; N, blue; C, grey; and H, green.

Crystal data

[Au2Fe(C11H14NOS)2(C17H14P)2]Z = 1
Mr = 1364.87F(000) = 668
Triclinic, P1Dx = 1.710 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71069 Å
a = 8.1631 (9) ÅCell parameters from 2346 reflections
b = 13.4959 (14) Åθ = 2.7–30.0°
c = 13.5154 (14) ŵ = 5.97 mm1
α = 107.440 (2)°T = 223 K
β = 97.401 (2)°Block, orange
γ = 106.366 (2)°0.21 × 0.07 × 0.04 mm
V = 1325.5 (2) Å3

Data collection

Bruker SMART CCD diffractometer4651 independent reflections
Radiation source: fine-focus sealed tube3790 reflections with I > 2σ(I)
graphiteRint = 0.036
ω scansθmax = 25.0°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Bruker, 2000)h = −9→5
Tmin = 0.629, Tmax = 1k = −16→15
7710 measured reflectionsl = −15→16

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.040Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.088H-atom parameters constrained
S = 0.98w = 1/[σ2(Fo2) + (0.0429P)2] where P = (Fo2 + 2Fc2)/3
4651 reflections(Δ/σ)max < 0.001
305 parametersΔρmax = 1.74 e Å3
0 restraintsΔρmin = −0.93 e Å3

Special details

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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)

xyzUiso*/Ueq
Au0.13463 (4)0.49437 (2)0.20439 (2)0.03125 (11)
Fe0.50000.50000.00000.0270 (3)
S10.1355 (3)0.63009 (17)0.35458 (14)0.0434 (5)
P10.1284 (2)0.35677 (14)0.05834 (13)0.0266 (4)
O10.4456 (6)0.6118 (4)0.4008 (3)0.0351 (11)
N10.3945 (9)0.7445 (5)0.5308 (5)0.0457 (17)
C10.3418 (10)0.6707 (6)0.4401 (6)0.0382 (18)
C20.2892 (11)0.8073 (7)0.5704 (6)0.046 (2)
C30.2959 (12)0.8999 (7)0.5460 (7)0.057 (2)
H30.36470.91850.49930.069*
C40.2016 (12)0.9663 (7)0.5898 (7)0.059 (2)
H40.20361.02700.56890.071*
C50.1061 (12)0.9464 (8)0.6622 (6)0.056 (2)
C60.1049 (13)0.8551 (9)0.6871 (6)0.062 (3)
H60.04060.83810.73630.075*
C70.1941 (12)0.7875 (8)0.6427 (7)0.056 (2)
H70.18970.72590.66250.068*
C80.0014 (15)1.0160 (9)0.7055 (8)0.087 (4)
H8A−0.10980.99240.65480.130*
H8B0.06571.09260.71780.130*
H8C−0.02011.00840.77230.130*
C90.6271 (10)0.6486 (7)0.4650 (6)0.046 (2)
H90.62560.66770.54140.055*
C100.6848 (11)0.5484 (7)0.4295 (6)0.047 (2)
H10A0.60750.48800.44410.071*
H10B0.80420.56660.46820.071*
H10C0.67940.52670.35360.071*
C110.7391 (11)0.7471 (7)0.4477 (7)0.060 (2)
H11A0.69550.80790.47260.091*
H11B0.73570.72980.37230.091*
H11C0.85900.76800.48700.091*
C120.2458 (8)0.4006 (5)−0.0322 (5)0.0263 (15)
C130.2562 (9)0.5014 (6)−0.0501 (5)0.0329 (16)
H130.20790.5535−0.01450.039*
C140.3500 (10)0.5101 (7)−0.1288 (6)0.044 (2)
H140.37470.5680−0.15580.053*
C150.4004 (10)0.4153 (7)−0.1600 (5)0.045 (2)
H150.46550.3996−0.21160.054*
C160.3375 (9)0.3480 (6)−0.1013 (5)0.0354 (17)
H160.35340.2804−0.10700.043*
C17−0.0903 (8)0.2718 (5)−0.0236 (5)0.0267 (15)
C18−0.2168 (10)0.2284 (6)0.0247 (6)0.0423 (19)
H18−0.18930.24310.09850.051*
C19−0.3841 (11)0.1631 (7)−0.0356 (8)0.058 (2)
H19−0.46950.1317−0.00300.070*
C20−0.4260 (11)0.1439 (7)−0.1435 (8)0.057 (2)
H20−0.53990.0997−0.18430.068*
C21−0.3025 (11)0.1890 (6)−0.1906 (7)0.049 (2)
H21−0.33230.1767−0.26380.059*
C22−0.1347 (10)0.2522 (6)−0.1327 (6)0.0384 (18)
H22−0.04990.2822−0.16630.046*
C230.2152 (8)0.2599 (5)0.0958 (5)0.0294 (15)
C240.3196 (10)0.2918 (7)0.1944 (6)0.0423 (19)
H240.35070.36480.24160.051*
C250.3806 (12)0.2174 (8)0.2258 (7)0.059 (2)
H250.45120.23980.29460.070*
C260.3391 (12)0.1131 (8)0.1582 (7)0.056 (2)
H260.38400.06390.17970.067*
C270.2318 (10)0.0772 (6)0.0580 (7)0.048 (2)
H270.20060.00360.01190.057*
C280.1709 (9)0.1516 (6)0.0263 (6)0.0400 (18)
H280.09930.1289−0.04220.048*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Au0.02798 (16)0.03521 (17)0.02566 (15)0.00940 (12)0.00453 (10)0.00587 (11)
Fe0.0229 (7)0.0322 (8)0.0227 (6)0.0055 (6)0.0028 (5)0.0098 (6)
S10.0352 (11)0.0527 (12)0.0320 (9)0.0184 (10)0.0026 (8)−0.0004 (9)
P10.0224 (9)0.0272 (9)0.0276 (9)0.0064 (8)0.0042 (7)0.0086 (8)
O10.028 (3)0.042 (3)0.029 (2)0.014 (2)0.000 (2)0.005 (2)
N10.046 (4)0.048 (4)0.033 (3)0.020 (3)−0.002 (3)0.003 (3)
C10.040 (4)0.035 (4)0.033 (4)0.003 (4)0.003 (3)0.015 (4)
C20.048 (5)0.054 (5)0.025 (4)0.019 (4)0.000 (4)0.003 (4)
C30.064 (6)0.051 (5)0.056 (5)0.016 (5)0.028 (5)0.016 (5)
C40.065 (6)0.040 (5)0.063 (6)0.016 (5)0.013 (5)0.008 (4)
C50.054 (6)0.068 (6)0.027 (4)0.018 (5)−0.002 (4)−0.005 (4)
C60.063 (6)0.092 (8)0.034 (4)0.027 (6)0.015 (4)0.023 (5)
C70.053 (5)0.075 (6)0.050 (5)0.032 (5)0.005 (4)0.028 (5)
C80.086 (8)0.099 (8)0.053 (6)0.048 (7)0.003 (6)−0.015 (6)
C90.036 (4)0.058 (5)0.031 (4)0.008 (4)−0.002 (3)0.011 (4)
C100.044 (5)0.070 (6)0.034 (4)0.027 (4)0.007 (4)0.021 (4)
C110.043 (5)0.051 (5)0.064 (6)−0.001 (4)−0.001 (4)0.009 (5)
C120.023 (3)0.025 (3)0.027 (3)0.006 (3)0.001 (3)0.007 (3)
C130.025 (4)0.037 (4)0.035 (4)0.010 (3)−0.002 (3)0.016 (3)
C140.043 (5)0.055 (5)0.032 (4)0.007 (4)−0.002 (4)0.023 (4)
C150.037 (4)0.064 (6)0.018 (3)0.002 (4)0.005 (3)0.007 (4)
C160.032 (4)0.037 (4)0.030 (4)0.009 (3)0.005 (3)0.006 (3)
C170.026 (4)0.016 (3)0.037 (4)0.007 (3)0.003 (3)0.009 (3)
C180.036 (4)0.044 (5)0.053 (5)0.014 (4)0.019 (4)0.022 (4)
C190.036 (5)0.044 (5)0.104 (8)0.011 (4)0.029 (5)0.035 (5)
C200.025 (4)0.042 (5)0.088 (7)0.006 (4)−0.009 (5)0.016 (5)
C210.036 (5)0.045 (5)0.049 (5)0.009 (4)−0.011 (4)0.006 (4)
C220.036 (4)0.038 (4)0.037 (4)0.012 (4)0.006 (3)0.009 (3)
C230.018 (3)0.028 (4)0.035 (4)−0.002 (3)0.007 (3)0.011 (3)
C240.041 (5)0.054 (5)0.036 (4)0.021 (4)0.007 (3)0.019 (4)
C250.072 (6)0.087 (7)0.041 (5)0.051 (6)0.015 (4)0.032 (5)
C260.066 (6)0.070 (6)0.072 (6)0.045 (5)0.037 (5)0.052 (6)
C270.040 (5)0.031 (4)0.074 (6)0.004 (4)0.019 (4)0.026 (4)
C280.025 (4)0.037 (4)0.052 (5)0.004 (3)0.003 (3)0.017 (4)

Geometric parameters (Å, °)

Au—S12.2883 (19)C10—H10A0.9700
Au—P12.2520 (17)C10—H10B0.9700
Fe—C13i2.025 (6)C10—H10C0.9700
Fe—C132.025 (6)C11—H11A0.9700
Fe—C122.036 (6)C11—H11B0.9700
Fe—C12i2.036 (6)C11—H11C0.9700
Fe—C162.039 (7)C12—C161.420 (9)
Fe—C16i2.039 (7)C12—C131.433 (9)
Fe—C152.046 (7)C13—C141.403 (10)
Fe—C15i2.046 (7)C13—H130.9400
Fe—C14i2.059 (7)C14—C151.416 (11)
Fe—C142.059 (7)C14—H140.9400
S1—C11.753 (7)C15—C161.411 (10)
P1—C121.784 (7)C15—H150.9400
P1—C231.814 (7)C16—H160.9400
P1—C171.818 (6)C17—C181.377 (10)
O1—C11.370 (9)C17—C221.396 (9)
O1—C91.479 (8)C18—C191.382 (11)
N1—C11.253 (9)C18—H180.9400
N1—C21.415 (10)C19—C201.381 (13)
C2—C71.365 (12)C19—H190.9400
C2—C31.373 (11)C20—C211.358 (12)
C3—C41.390 (12)C20—H200.9400
C3—H30.9400C21—C221.371 (10)
C4—C51.369 (12)C21—H210.9400
C4—H40.9400C22—H220.9400
C5—C61.369 (13)C23—C241.358 (9)
C5—C81.485 (12)C23—C281.393 (10)
C6—C71.372 (12)C24—C251.386 (10)
C6—H60.9400C24—H240.9400
C7—H70.9400C25—C261.346 (12)
C8—H8A0.9700C25—H250.9400
C8—H8B0.9700C26—C271.378 (12)
C8—H8C0.9700C26—H260.9400
C9—C111.488 (11)C27—C281.387 (10)
C9—C101.519 (10)C27—H270.9400
C9—H90.9900C28—H280.9400
P1—Au—S1178.17 (8)O1—C9—C10104.7 (6)
C13i—Fe—C13180.0C11—C9—C10113.9 (7)
C13i—Fe—C12138.7 (3)O1—C9—H9109.3
C13—Fe—C1241.3 (3)C11—C9—H9109.3
C13i—Fe—C12i41.3 (3)C10—C9—H9109.3
C13—Fe—C12i138.7 (3)C9—C10—H10A109.5
C12—Fe—C12i180.0C9—C10—H10B109.5
C13i—Fe—C16111.4 (3)H10A—C10—H10B109.5
C13—Fe—C1668.6 (3)C9—C10—H10C109.5
C12—Fe—C1640.8 (3)H10A—C10—H10C109.5
C12i—Fe—C16139.2 (3)H10B—C10—H10C109.5
C13i—Fe—C16i68.6 (3)C9—C11—H11A109.5
C13—Fe—C16i111.4 (3)C9—C11—H11B109.5
C12—Fe—C16i139.2 (3)H11A—C11—H11B109.5
C12i—Fe—C16i40.8 (3)C9—C11—H11C109.5
C16—Fe—C16i180.0 (4)H11A—C11—H11C109.5
C13i—Fe—C15112.4 (3)H11B—C11—H11C109.5
C13—Fe—C1567.6 (3)C16—C12—C13106.7 (6)
C12—Fe—C1568.2 (3)C16—C12—P1130.5 (5)
C12i—Fe—C15111.8 (3)C13—C12—P1122.8 (5)
C16—Fe—C1540.4 (3)C16—C12—Fe69.7 (4)
C16i—Fe—C15139.6 (3)C13—C12—Fe68.9 (4)
C13i—Fe—C15i67.6 (3)P1—C12—Fe127.9 (3)
C13—Fe—C15i112.4 (3)C14—C13—C12109.3 (7)
C12—Fe—C15i111.8 (3)C14—C13—Fe71.2 (4)
C12i—Fe—C15i68.2 (3)C12—C13—Fe69.7 (4)
C16—Fe—C15i139.6 (3)C14—C13—H13125.4
C16i—Fe—C15i40.4 (3)C12—C13—H13125.4
C15—Fe—C15i180.0 (2)Fe—C13—H13125.3
C13i—Fe—C14i40.2 (3)C13—C14—C15107.0 (7)
C13—Fe—C14i139.8 (3)C13—C14—Fe68.6 (4)
C12—Fe—C14i111.2 (3)C15—C14—Fe69.3 (4)
C12i—Fe—C14i68.8 (3)C13—C14—H14126.5
C16—Fe—C14i111.6 (3)C15—C14—H14126.5
C16i—Fe—C14i68.4 (3)Fe—C14—H14127.1
C15—Fe—C14i139.6 (3)C16—C15—C14109.2 (7)
C15i—Fe—C14i40.4 (3)C16—C15—Fe69.5 (4)
C13i—Fe—C14139.8 (3)C14—C15—Fe70.3 (4)
C13—Fe—C1440.2 (3)C16—C15—H15125.4
C12—Fe—C1468.8 (3)C14—C15—H15125.4
C12i—Fe—C14111.2 (3)Fe—C15—H15126.3
C16—Fe—C1468.4 (3)C15—C16—C12107.9 (7)
C16i—Fe—C14111.6 (3)C15—C16—Fe70.1 (4)
C15—Fe—C1440.4 (3)C12—C16—Fe69.5 (4)
C15i—Fe—C14139.6 (3)C15—C16—H16126.0
C14i—Fe—C14180.000 (1)C12—C16—H16126.0
C1—S1—Au105.7 (3)Fe—C16—H16126.0
C12—P1—C23108.0 (3)C18—C17—C22119.3 (7)
C12—P1—C17104.2 (3)C18—C17—P1118.6 (5)
C23—P1—C17104.0 (3)C22—C17—P1122.1 (6)
C12—P1—Au114.8 (2)C17—C18—C19119.9 (8)
C23—P1—Au110.6 (2)C17—C18—H18120.0
C17—P1—Au114.5 (2)C19—C18—H18120.0
C1—O1—C9116.5 (5)C20—C19—C18120.1 (8)
C1—N1—C2120.7 (7)C20—C19—H19120.0
N1—C1—O1120.6 (7)C18—C19—H19120.0
N1—C1—S1125.4 (6)C21—C20—C19120.0 (8)
O1—C1—S1114.0 (5)C21—C20—H20120.0
C7—C2—C3117.1 (8)C19—C20—H20120.0
C7—C2—N1122.6 (8)C20—C21—C22120.8 (8)
C3—C2—N1119.9 (8)C20—C21—H21119.6
C2—C3—C4120.5 (9)C22—C21—H21119.6
C2—C3—H3119.7C21—C22—C17119.8 (8)
C4—C3—H3119.7C21—C22—H22120.1
C5—C4—C3122.4 (9)C17—C22—H22120.1
C5—C4—H4118.8C24—C23—C28119.2 (7)
C3—C4—H4118.8C24—C23—P1119.8 (5)
C6—C5—C4115.9 (9)C28—C23—P1121.0 (5)
C6—C5—C8122.3 (10)C23—C24—C25120.4 (8)
C4—C5—C8121.7 (10)C23—C24—H24119.8
C5—C6—C7122.3 (9)C25—C24—H24119.8
C5—C6—H6118.8C26—C25—C24120.2 (8)
C7—C6—H6118.8C26—C25—H25119.9
C2—C7—C6121.7 (9)C24—C25—H25119.9
C2—C7—H7119.1C25—C26—C27121.1 (7)
C6—C7—H7119.1C25—C26—H26119.5
C5—C8—H8A109.5C27—C26—H26119.5
C5—C8—H8B109.5C26—C27—C28118.7 (8)
H8A—C8—H8B109.5C26—C27—H27120.6
C5—C8—H8C109.5C28—C27—H27120.6
H8A—C8—H8C109.5C27—C28—C23120.3 (7)
H8B—C8—H8C109.5C27—C28—H28119.9
O1—C9—C11110.2 (6)C23—C28—H28119.9
C2—N1—C1—O1178.4 (7)C16—Fe—C14—C1381.9 (5)
C2—N1—C1—S1−3.5 (11)C16i—Fe—C14—C13−98.1 (5)
C9—O1—C1—N1−6.9 (10)C15—Fe—C14—C13118.9 (6)
C9—O1—C1—S1174.8 (5)C15i—Fe—C14—C13−61.1 (6)
Au—S1—C1—N1179.4 (6)C13i—Fe—C14—C1561.1 (6)
Au—S1—C1—O1−2.4 (6)C13—Fe—C14—C15−118.9 (6)
C1—N1—C2—C7101.8 (9)C12—Fe—C14—C15−80.9 (5)
C1—N1—C2—C3−85.8 (10)C12i—Fe—C14—C1599.1 (5)
C7—C2—C3—C4−3.1 (13)C16—Fe—C14—C15−37.0 (4)
N1—C2—C3—C4−175.9 (7)C16i—Fe—C14—C15143.0 (4)
C2—C3—C4—C53.3 (14)C15i—Fe—C14—C15180.0
C3—C4—C5—C6−1.7 (13)C13—C14—C15—C160.3 (8)
C3—C4—C5—C8−178.0 (9)Fe—C14—C15—C1658.8 (5)
C4—C5—C6—C70.2 (13)C13—C14—C15—Fe−58.5 (5)
C8—C5—C6—C7176.4 (8)C13i—Fe—C15—C1697.3 (5)
C3—C2—C7—C61.7 (12)C13—Fe—C15—C16−82.7 (5)
N1—C2—C7—C6174.3 (8)C12—Fe—C15—C16−38.0 (4)
C5—C6—C7—C2−0.3 (14)C12i—Fe—C15—C16142.0 (4)
C1—O1—C9—C11−78.4 (8)C14i—Fe—C15—C1659.6 (6)
C1—O1—C9—C10158.6 (6)C14—Fe—C15—C16−120.4 (6)
C23—P1—C12—C1624.5 (7)C13i—Fe—C15—C14−142.3 (4)
C17—P1—C12—C16−85.7 (6)C13—Fe—C15—C1437.7 (4)
Au—P1—C12—C16148.3 (5)C12—Fe—C15—C1482.4 (5)
C23—P1—C12—C13−158.2 (5)C12i—Fe—C15—C14−97.6 (5)
C17—P1—C12—C1391.7 (5)C16—Fe—C15—C14120.4 (6)
Au—P1—C12—C13−34.4 (6)C16i—Fe—C15—C14−59.6 (6)
C23—P1—C12—Fe−70.5 (5)C14—C15—C16—C120.1 (8)
C17—P1—C12—Fe179.3 (4)Fe—C15—C16—C1259.4 (5)
Au—P1—C12—Fe53.3 (4)C14—C15—C16—Fe−59.3 (5)
C13i—Fe—C12—C16−62.0 (6)C13—C12—C16—C15−0.5 (7)
C13—Fe—C12—C16118.0 (6)P1—C12—C16—C15177.2 (5)
C16i—Fe—C12—C16180.0Fe—C12—C16—C15−59.8 (5)
C15—Fe—C12—C1637.6 (4)C13—C12—C16—Fe59.3 (4)
C15i—Fe—C12—C16−142.4 (4)P1—C12—C16—Fe−123.0 (6)
C14i—Fe—C12—C16−98.9 (4)C13i—Fe—C16—C15−99.8 (5)
C14—Fe—C12—C1681.1 (4)C13—Fe—C16—C1580.2 (5)
C13i—Fe—C12—C13180.0C12—Fe—C16—C15119.0 (6)
C16—Fe—C12—C13−118.0 (6)C12i—Fe—C16—C15−61.0 (6)
C16i—Fe—C12—C1362.0 (6)C14i—Fe—C16—C15−143.1 (5)
C15—Fe—C12—C13−80.4 (4)C14—Fe—C16—C1536.9 (5)
C15i—Fe—C12—C1399.6 (4)C13i—Fe—C16—C12141.2 (4)
C14i—Fe—C12—C13143.1 (4)C13—Fe—C16—C12−38.8 (4)
C14—Fe—C12—C13−36.9 (4)C12i—Fe—C16—C12180.0
C13i—Fe—C12—P164.2 (6)C15—Fe—C16—C12−119.0 (6)
C13—Fe—C12—P1−115.8 (6)C15i—Fe—C16—C1261.0 (6)
C16—Fe—C12—P1126.1 (6)C14i—Fe—C16—C1297.9 (4)
C16i—Fe—C12—P1−53.9 (6)C14—Fe—C16—C12−82.1 (4)
C15—Fe—C12—P1163.8 (5)C12—P1—C17—C18−177.4 (5)
C15i—Fe—C12—P1−16.2 (5)C23—P1—C17—C1869.6 (6)
C14i—Fe—C12—P127.3 (5)Au—P1—C17—C18−51.2 (6)
C14—Fe—C12—P1−152.7 (5)C12—P1—C17—C220.7 (6)
C16—C12—C13—C140.7 (7)C23—P1—C17—C22−112.3 (6)
P1—C12—C13—C14−177.2 (5)Au—P1—C17—C22126.9 (5)
Fe—C12—C13—C1460.5 (5)C22—C17—C18—C192.1 (10)
C16—C12—C13—Fe−59.8 (4)P1—C17—C18—C19−179.7 (6)
P1—C12—C13—Fe122.3 (5)C17—C18—C19—C20−1.8 (12)
C12—Fe—C13—C14−119.8 (6)C18—C19—C20—C210.2 (13)
C12i—Fe—C13—C1460.2 (6)C19—C20—C21—C221.1 (12)
C16—Fe—C13—C14−81.5 (5)C20—C21—C22—C17−0.8 (12)
C16i—Fe—C13—C1498.5 (5)C18—C17—C22—C21−0.8 (10)
C15—Fe—C13—C14−37.8 (5)P1—C17—C22—C21−178.9 (6)
C15i—Fe—C13—C14142.2 (5)C12—P1—C23—C24106.1 (6)
C14i—Fe—C13—C14180.0C17—P1—C23—C24−143.6 (6)
C12i—Fe—C13—C12180.0Au—P1—C23—C24−20.2 (6)
C16—Fe—C13—C1238.3 (4)C12—P1—C23—C28−76.4 (6)
C16i—Fe—C13—C12−141.7 (4)C17—P1—C23—C2833.9 (7)
C15—Fe—C13—C1282.0 (4)Au—P1—C23—C28157.3 (5)
C15i—Fe—C13—C12−98.0 (4)C28—C23—C24—C25−0.3 (12)
C14i—Fe—C13—C12−60.2 (6)P1—C23—C24—C25177.2 (6)
C14—Fe—C13—C12119.8 (6)C23—C24—C25—C261.0 (13)
C12—C13—C14—C15−0.6 (7)C24—C25—C26—C27−1.8 (14)
Fe—C13—C14—C1559.0 (5)C25—C26—C27—C281.9 (13)
C12—C13—C14—Fe−59.6 (4)C26—C27—C28—C23−1.2 (12)
C13i—Fe—C14—C13180.0C24—C23—C28—C270.4 (11)
C12—Fe—C14—C1337.9 (4)P1—C23—C28—C27−177.0 (6)
C12i—Fe—C14—C13−142.1 (4)

Symmetry codes: (i) −x+1, −y+1, −z.

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C25—H25···N1ii0.942.453.370 (11)167

Symmetry codes: (ii) −x+1, −y+1, −z+1.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB5221).

References

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