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Acta Crystallogr Sect E Struct Rep Online. 2010 February 1; 66(Pt 2): m212.
Published online 2010 January 30. doi:  10.1107/S1600536810002886
PMCID: PMC2979940

Bis(tribenzyl­ammonium) tetra­chloridoaurate(III) chloride

Abstract

In the title compound, (C21H22N)2[AuCl4]Cl, the AuIII atom adopts a square-planar coordination geometry defined by four chloride ions. In the crystal structure, inter­molecular N—H(...)Cl hydrogen bonds link the organic cations and the uncoordinated chloride ion.

Related literature

For related structures, see: Calleja et al. (2001 [triangle]); Hasan et al. (1999 [triangle]); Hojjat Kashani et al. (2008 [triangle]); Jarvinen et al. (1988 [triangle]); Johnson & Steed (1998 [triangle]); Safari et al. (2009 [triangle]); Yıldırım et al. (2009a [triangle],b [triangle]); Yap et al. (1995 [triangle]); Yousefi et al. (2007 [triangle]); Zeng et al. (1994 [triangle]); Zhang et al. (2006 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-0m212-scheme1.jpg

Experimental

Crystal data

  • (C21H22N)2[AuCl4]Cl
  • M r = 951.01
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-0m212-efi1.jpg
  • a = 11.135 (1) Å
  • b = 13.7920 (11) Å
  • c = 13.8417 (12) Å
  • α = 95.894 (7)°
  • β = 100.300 (7)°
  • γ = 95.222 (7)°
  • V = 2067.4 (3) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 3.91 mm−1
  • T = 298 K
  • 0.35 × 0.32 × 0.27 mm

Data collection

  • Stoe IPDS II diffractometer
  • Absorption correction: numerical (X-RED; Stoe & Cie, 2005 [triangle]) T min = 0.280, T max = 0.350
  • 28425 measured reflections
  • 12513 independent reflections
  • 10542 reflections with I > 2σ(I)
  • R int = 0.075

Refinement

  • R[F 2 > 2σ(F 2)] = 0.051
  • wR(F 2) = 0.144
  • S = 1.11
  • 12513 reflections
  • 451 parameters
  • H-atom parameters constrained
  • Δρmax = 1.82 e Å−3
  • Δρmin = −2.10 e Å−3

Data collection: X-AREA (Stoe & Cie, 2005 [triangle]); cell refinement: X-AREA; data reduction: X-RED (Stoe & Cie, 2005 [triangle]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: ORTEP-3 (Farrugia, 1997 [triangle]); software used to prepare material for publication: WinGX (Farrugia, 1999 [triangle]).

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

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810002886/hb5291sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810002886/hb5291Isup2.hkl

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

Acknowledgments

We are grateful to Shahid Beheshti University for financial support.

supplementary crystallographic information

Comment

There are several proton transfer systems using tribenzylamine, with proton donor molecules, such as {(TBA)(DBA)[CuCl4]}, (II), (Zeng et al., 1994), (TBA)[DCHSTO], (III), (Jarvine et al., 1988) and {(TBA)3[PtCl6]Cl}, (IV), (Yousefi et al., 2007) [where TBA is tribenzylammonium, DBA is dibenzylammonium and DCHSTO is 1,1,1,1,2,2,2,3,3,3-decacarbonyl-2,3-(µ-hydrido) -2,3-(µ-sulfonyl)-triangulo-tri-osmium] have been synthesized and characterized by single-crystal X-ray diffraction methods.

There are also several proton transfer systems using HAuCl4 with proton acceptor molecules, such as [EMI][AuCl4], (V) and [BMI]2[AuCl4].2H2O, (VI), (Hasan et al., 1999), [H2bipy][AuCl4][Cl], (VII), (Zhang et al., 2006), [H7O3][15-crown-5][AuCl4], (VIII) and [H5O2][benzo-15-crown-5]2[AuCl4], (IX), (Johnson & Steed, 1998), [H5O2]2[12-crown-4]2[AuCl4]2, (X), [H3O][18-crown-6][AuCl4], (XI) and [H3O] [4-nitrobenzo-18-crown-6][AuCl4], (XII), (Calleja et al., 2001), [DPpy.H][AuCl4], (XIII), (Yap et al., 1995), [H2DA18C6][AuCl4].2H2O, (XIV), (Hojjat Kashani et al., 2008), [dafonium][dafone][AuCl4], (XV), (Safari et al., 2009), [pz(py)2.H][AuCl4], (XVI), (Yıldırım, Akkurt, Safari et al., 2009a), [Ph2Phen.H][AuCl4], (XVII), (Yıldırım, Akkurt, Safari, Abedi et al., 2009b) [Where EMI is 1-ethyl-3-methylimidazolium, BMI is 1-butyl-3-methylimidazolium, H2bipy is 2,2'-bipyridinium, DPpy.H is 2,6-diphenylpyridinium, H2DA18C6 is 1,10-diazonia-18-crown-6, dafonium is 9-oxo-4,5-diazafluoren-4-ium, dafone is 4,5-diazafluoren-9-one, pz(py)2.H is 2-(3-pyridin-2-ylpyrazin-2-yl)pyridinium and Ph2Phen.H is 2,9-dimethyl-4,7-diphenyl-1,10- phenanthrolin-1-ium] have been synthesized and characterized by single-crystal X-ray diffraction methods. We report herein the synthesis and crystal structure of the title compound, (I).

The molecule of the title compound, (I), (Fig. 1), contains two independent protonated tribenzylammonium cations and [AuCl4]- and Cl- anions. The AuIII atom has a squareplanar environment defined by four Cl atoms. The bond lengths and angles, in cation, are in good agreement with the corresponding values in (II), (III) and (IV). In [AuCl4]- anion, the Au—Cl bond lengths and angles (Table 1) are within normal range (X, XIII, XIV, XV and XVI).

In the crystal structure, intermolecular N—H···Cl hydrogen bonds (Table 2) result in the formation of a supramolecular structure (Fig. 2).

Experimental

A solution of tribenzylamine (0.22 g, 0.74 mmol) in methanol (15 ml) was added to a solution of HAuCl4.3H2O, (0.29 g, 0.74 mmol) in acetonitrile (15 ml) and the resulting yellow solution was stirred for 30 min at 313 K. Then, it was left to evaporate slowly at room temperature. After five days, yellow blocks of (I) were isolated (yield 0.50 g; 71.1%; m.p. < 573 K).

Refinement

All H atoms were positioned geometrically, with C—H = 0.93Å and constrained to ride on their parent atoms, with Uiso(H) = 1.2Ueq(C).

Figures

Fig. 1.
The molecular structure of (I). Displacement ellipsoids are drawn at the 30% probability level.
Fig. 2.
Unit-cell packing diagram for (I). Hydrogen bonds are shown as dashed lines.

Crystal data

(C21H22N)2[AuCl4]ClZ = 2
Mr = 951.01F(000) = 948
Triclinic, P1Dx = 1.528 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 11.135 (1) ÅCell parameters from 1237 reflections
b = 13.7920 (11) Åθ = 1.9–30.6°
c = 13.8417 (12) ŵ = 3.91 mm1
α = 95.894 (7)°T = 298 K
β = 100.300 (7)°Block, yellow
γ = 95.222 (7)°0.35 × 0.32 × 0.27 mm
V = 2067.4 (3) Å3

Data collection

Stoe IPDS II diffractometer12513 independent reflections
Radiation source: fine-focus sealed tube10542 reflections with I > 2σ(I)
graphiteRint = 0.075
Detector resolution: 0.15 mm pixels mm-1θmax = 30.6°, θmin = 1.9°
rotation method scansh = −15→15
Absorption correction: numerical (X-RED; Stoe & Cie, 2005)k = −19→19
Tmin = 0.280, Tmax = 0.350l = −19→19
28425 measured reflections

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)] = 0.051Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.144H-atom parameters constrained
S = 1.11w = 1/[σ2(Fo2) + (0.0689P)2 + 1.4093P] where P = (Fo2 + 2Fc2)/3
12513 reflections(Δ/σ)max = 0.002
451 parametersΔρmax = 1.82 e Å3
0 restraintsΔρmin = −2.10 e Å3

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.
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)

xyzUiso*/Ueq
C10.3537 (5)0.9891 (3)0.3590 (4)0.0603 (11)
H1A0.43260.96670.38240.072*
H1B0.36901.05420.33990.072*
C20.2835 (4)0.9955 (3)0.4423 (4)0.0568 (10)
C30.2041 (5)1.0661 (4)0.4502 (4)0.0688 (13)
H30.19351.10980.40320.083*
C40.1403 (6)1.0724 (6)0.5269 (6)0.087 (2)
H40.08611.11940.53090.104*
C50.1563 (8)1.0110 (7)0.5954 (6)0.098 (3)
H50.11331.01610.64710.117*
C60.2359 (8)0.9397 (6)0.5909 (5)0.092 (2)
H60.24650.89730.63910.110*
C70.2996 (6)0.9327 (4)0.5134 (5)0.0724 (14)
H70.35340.88530.50950.087*
C80.2330 (6)0.9805 (4)0.1885 (5)0.0680 (13)
H8A0.17811.02180.21570.082*
H8B0.29971.02360.17420.082*
C90.1643 (5)0.9255 (3)0.0930 (4)0.0624 (11)
C100.2214 (8)0.9082 (6)0.0137 (6)0.091 (2)
H100.30510.92750.02060.109*
C110.1552 (12)0.8619 (8)−0.0770 (6)0.116 (3)
H110.19520.8477−0.12940.140*
C120.0306 (13)0.8374 (7)−0.0885 (7)0.119 (4)
H12−0.01460.8087−0.14940.142*
C13−0.0264 (8)0.8554 (5)−0.0104 (6)0.092 (2)
H13−0.11040.8374−0.01810.111*
C140.0386 (6)0.9001 (4)0.0804 (5)0.0710 (14)
H14−0.00190.91310.13270.085*
C150.3678 (5)0.8484 (4)0.2333 (4)0.0622 (11)
H15A0.43870.88430.21650.075*
H15B0.32340.80800.17400.075*
C160.4110 (4)0.7832 (3)0.3102 (4)0.0547 (9)
C170.5296 (5)0.7974 (4)0.3657 (5)0.0694 (13)
H170.58580.84690.35400.083*
C180.5642 (6)0.7389 (5)0.4377 (5)0.0822 (18)
H180.64350.74950.47490.099*
C190.4823 (8)0.6642 (6)0.4556 (6)0.092 (2)
H190.50590.62470.50460.110*
C200.3664 (7)0.6496 (5)0.4004 (6)0.089 (2)
H200.31110.59960.41230.107*
C210.3291 (6)0.7067 (4)0.3276 (5)0.0709 (14)
H210.25000.69470.29010.085*
C220.0653 (5)0.4432 (4)0.6633 (4)0.0592 (10)
H22A−0.02060.44790.66550.071*
H22B0.10760.50920.67680.071*
C230.0748 (5)0.4012 (3)0.5602 (3)0.0533 (9)
C240.1722 (5)0.4335 (4)0.5175 (4)0.0630 (11)
H240.23130.48260.55250.076*
C250.1835 (6)0.3944 (5)0.4239 (4)0.0707 (14)
H250.25040.41590.39690.085*
C260.0949 (7)0.3235 (5)0.3713 (4)0.0771 (16)
H260.10190.29670.30830.093*
C27−0.0033 (7)0.2920 (5)0.4106 (4)0.0820 (18)
H27−0.06380.24490.37390.098*
C28−0.0135 (5)0.3306 (5)0.5063 (4)0.0684 (13)
H28−0.08010.30830.53320.082*
C290.2478 (4)0.3628 (4)0.7359 (4)0.0606 (11)
H29A0.24520.32570.67190.073*
H29B0.29850.42440.73840.073*
C300.3066 (4)0.3067 (5)0.8150 (4)0.0605 (11)
C310.4046 (6)0.3513 (7)0.8857 (5)0.093 (2)
H310.43130.41730.88650.112*
C320.4632 (8)0.2975 (12)0.9557 (7)0.132 (4)
H320.52930.32771.00340.159*
C330.4255 (11)0.2024 (12)0.9551 (7)0.134 (5)
H330.46500.16741.00290.160*
C340.3298 (10)0.1564 (8)0.8852 (8)0.115 (3)
H340.30510.09000.88480.138*
C350.2689 (6)0.2088 (5)0.8143 (5)0.0784 (16)
H350.20320.17780.76680.094*
C360.1151 (4)0.4354 (4)0.8449 (3)0.0590 (11)
H36A0.16160.49970.85300.071*
H36B0.15560.39830.89450.071*
C37−0.0122 (4)0.4478 (3)0.8636 (3)0.0525 (9)
C38−0.0641 (7)0.5326 (5)0.8472 (5)0.0783 (16)
H38−0.02200.58260.82210.094*
C39−0.1807 (8)0.5434 (7)0.8686 (6)0.099 (3)
H39−0.21640.60030.85590.118*
C40−0.2417 (7)0.4738 (8)0.9066 (6)0.093 (2)
H40−0.31960.48180.91930.112*
C41−0.1895 (6)0.3906 (6)0.9269 (5)0.084 (2)
H41−0.23100.34300.95550.101*
C42−0.0750 (5)0.3766 (4)0.9053 (4)0.0644 (12)
H42−0.04030.31950.91870.077*
N10.2864 (4)0.9198 (3)0.2678 (3)0.0530 (8)
H1C0.22250.88470.28580.064*
N20.1179 (3)0.3846 (3)0.7443 (3)0.0480 (7)
H20.07000.32620.73630.058*
Cl10.27943 (18)0.67440 (18)0.7747 (3)0.1484 (13)
Cl20.45070 (15)0.88061 (11)0.80407 (14)0.0772 (4)
Cl30.67313 (17)0.76296 (12)0.7524 (2)0.1114 (8)
Cl40.49931 (17)0.56099 (11)0.71556 (16)0.0871 (5)
Cl50.04611 (12)0.81169 (9)0.30405 (10)0.0636 (3)
Au10.475074 (16)0.719913 (12)0.760740 (14)0.05584 (7)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C10.053 (2)0.046 (2)0.075 (3)−0.0076 (18)0.007 (2)−0.006 (2)
C20.052 (2)0.047 (2)0.064 (3)−0.0038 (17)−0.0008 (19)−0.0004 (18)
C30.069 (3)0.062 (3)0.070 (3)0.011 (2)0.002 (2)−0.004 (2)
C40.068 (3)0.096 (5)0.087 (4)0.005 (3)0.011 (3)−0.025 (4)
C50.090 (5)0.121 (7)0.070 (4)−0.019 (5)0.016 (4)−0.017 (4)
C60.107 (5)0.087 (4)0.068 (4)−0.019 (4)−0.005 (4)0.012 (3)
C70.078 (3)0.059 (3)0.072 (3)0.001 (2)−0.005 (3)0.009 (2)
C80.071 (3)0.044 (2)0.086 (4)0.000 (2)0.007 (3)0.011 (2)
C90.071 (3)0.045 (2)0.073 (3)0.007 (2)0.011 (2)0.015 (2)
C100.098 (5)0.098 (5)0.089 (5)0.027 (4)0.032 (4)0.027 (4)
C110.157 (9)0.136 (8)0.067 (4)0.067 (7)0.025 (5)0.014 (4)
C120.178 (11)0.085 (5)0.075 (5)0.029 (6)−0.022 (6)−0.004 (4)
C130.099 (5)0.073 (4)0.090 (5)−0.007 (3)−0.021 (4)0.022 (3)
C140.074 (3)0.062 (3)0.076 (3)0.004 (2)0.006 (3)0.017 (2)
C150.065 (3)0.056 (2)0.068 (3)0.009 (2)0.021 (2)0.005 (2)
C160.054 (2)0.053 (2)0.056 (2)0.0082 (18)0.0115 (19)−0.0006 (18)
C170.053 (2)0.066 (3)0.090 (4)0.008 (2)0.017 (3)0.004 (3)
C180.067 (3)0.083 (4)0.088 (4)0.018 (3)−0.008 (3)0.000 (3)
C190.103 (5)0.076 (4)0.096 (5)0.028 (4)0.004 (4)0.021 (3)
C200.088 (4)0.061 (3)0.116 (6)0.006 (3)0.006 (4)0.029 (3)
C210.063 (3)0.052 (3)0.091 (4)0.001 (2)−0.003 (3)0.011 (2)
C220.070 (3)0.056 (2)0.052 (2)0.012 (2)0.008 (2)0.0113 (18)
C230.061 (2)0.052 (2)0.046 (2)0.0107 (18)0.0032 (18)0.0116 (16)
C240.063 (3)0.063 (3)0.061 (3)−0.002 (2)0.006 (2)0.018 (2)
C250.079 (4)0.072 (3)0.065 (3)0.010 (3)0.017 (3)0.023 (3)
C260.107 (5)0.075 (3)0.052 (3)0.020 (3)0.013 (3)0.013 (2)
C270.096 (4)0.084 (4)0.054 (3)−0.008 (3)−0.006 (3)0.005 (3)
C280.065 (3)0.078 (3)0.056 (3)−0.007 (2)−0.001 (2)0.016 (2)
C290.047 (2)0.082 (3)0.055 (2)0.008 (2)0.0089 (19)0.019 (2)
C300.043 (2)0.090 (4)0.050 (2)0.012 (2)0.0066 (17)0.017 (2)
C310.058 (3)0.143 (7)0.071 (4)0.003 (4)−0.005 (3)0.016 (4)
C320.074 (5)0.246 (15)0.072 (4)0.035 (7)−0.014 (4)0.032 (7)
C330.121 (8)0.220 (13)0.090 (6)0.097 (9)0.026 (5)0.079 (8)
C340.123 (7)0.134 (8)0.112 (6)0.049 (6)0.040 (6)0.068 (6)
C350.076 (4)0.083 (4)0.081 (4)0.022 (3)0.010 (3)0.027 (3)
C360.054 (2)0.068 (3)0.047 (2)−0.001 (2)−0.0006 (18)−0.0025 (19)
C370.059 (2)0.053 (2)0.0426 (18)0.0084 (18)0.0023 (17)0.0007 (16)
C380.101 (5)0.068 (3)0.071 (3)0.026 (3)0.018 (3)0.018 (3)
C390.106 (6)0.112 (6)0.081 (4)0.068 (5)0.002 (4)0.007 (4)
C400.062 (3)0.131 (7)0.079 (4)0.025 (4)0.002 (3)−0.016 (4)
C410.076 (4)0.096 (5)0.076 (4)−0.017 (3)0.027 (3)−0.014 (3)
C420.075 (3)0.056 (3)0.060 (3)0.006 (2)0.014 (2)−0.001 (2)
N10.0501 (18)0.0395 (16)0.067 (2)−0.0057 (13)0.0113 (16)0.0031 (15)
N20.0433 (16)0.0518 (18)0.0465 (17)0.0007 (13)0.0054 (13)0.0048 (14)
Cl10.0593 (9)0.0925 (14)0.282 (4)−0.0136 (9)0.0373 (15)−0.0173 (19)
Cl20.0738 (8)0.0579 (7)0.0990 (10)0.0136 (6)0.0098 (7)0.0116 (6)
Cl30.0754 (9)0.0559 (7)0.217 (3)0.0043 (7)0.0601 (13)0.0278 (11)
Cl40.0884 (10)0.0512 (6)0.1191 (13)0.0014 (6)0.0184 (9)0.0055 (7)
Cl50.0573 (6)0.0615 (6)0.0690 (7)−0.0125 (5)0.0167 (5)0.0028 (5)
Au10.05173 (10)0.04902 (10)0.06372 (12)0.00099 (6)0.00227 (7)0.01189 (7)

Geometric parameters (Å, °)

C1—C21.504 (8)C22—H22B0.9700
C1—N11.533 (6)C23—C281.373 (7)
C1—H1A0.9700C23—C241.386 (7)
C1—H1B0.9700C24—C251.382 (8)
C2—C71.376 (8)C24—H240.9300
C2—C31.381 (7)C25—C261.371 (9)
C3—C41.379 (10)C25—H250.9300
C3—H30.9300C26—C271.362 (10)
C4—C51.334 (13)C26—H260.9300
C4—H40.9300C27—C281.403 (9)
C5—C61.386 (13)C27—H270.9300
C5—H50.9300C28—H280.9300
C6—C71.388 (11)C29—C301.496 (7)
C6—H60.9300C29—N21.525 (6)
C7—H70.9300C29—H29A0.9700
C8—C91.496 (8)C29—H29B0.9700
C8—N11.518 (7)C30—C351.375 (9)
C8—H8A0.9700C30—C311.378 (8)
C8—H8B0.9700C31—C321.388 (13)
C9—C101.374 (9)C31—H310.9300
C9—C141.387 (8)C32—C331.339 (18)
C10—C111.394 (13)C32—H320.9300
C10—H100.9300C33—C341.363 (16)
C11—C121.375 (16)C33—H330.9300
C11—H110.9300C34—C351.393 (10)
C12—C131.361 (14)C34—H340.9300
C12—H120.9300C35—H350.9300
C13—C141.384 (9)C36—N21.501 (6)
C13—H130.9300C36—C371.506 (7)
C14—H140.9300C36—H36A0.9700
C15—N11.497 (6)C36—H36B0.9700
C15—C161.505 (7)C37—C381.373 (8)
C15—H15A0.9700C37—C421.387 (7)
C15—H15B0.9700C38—C391.400 (11)
C16—C171.390 (7)C38—H380.9300
C16—C211.399 (8)C39—C401.332 (13)
C17—C181.369 (10)C39—H390.9300
C17—H170.9300C40—C411.364 (12)
C18—C191.385 (11)C40—H400.9300
C18—H180.9300C41—C421.386 (9)
C19—C201.364 (11)C41—H410.9300
C19—H190.9300C42—H420.9300
C20—C211.371 (9)N1—H1C0.9100
C20—H200.9300N2—H20.9100
C21—H210.9300Au1—Cl12.259 (2)
C22—C231.510 (7)Au1—Cl22.2891 (15)
C22—N21.514 (6)Au1—Cl32.2574 (17)
C22—H22A0.9700Au1—Cl42.2703 (15)
C2—C1—N1113.4 (4)C25—C24—C23121.5 (5)
C2—C1—H1A108.9C25—C24—H24119.2
N1—C1—H1A108.9C23—C24—H24119.2
C2—C1—H1B108.9C26—C25—C24119.3 (6)
N1—C1—H1B108.9C26—C25—H25120.4
H1A—C1—H1B107.7C24—C25—H25120.4
C7—C2—C3118.8 (6)C27—C26—C25120.4 (6)
C7—C2—C1120.5 (5)C27—C26—H26119.8
C3—C2—C1120.7 (5)C25—C26—H26119.8
C4—C3—C2120.7 (7)C26—C27—C28120.2 (6)
C4—C3—H3119.7C26—C27—H27119.9
C2—C3—H3119.7C28—C27—H27119.9
C5—C4—C3120.1 (7)C23—C28—C27120.1 (6)
C5—C4—H4120.0C23—C28—H28120.0
C3—C4—H4120.0C27—C28—H28120.0
C4—C5—C6121.2 (8)C30—C29—N2113.9 (4)
C4—C5—H5119.4C30—C29—H29A108.8
C6—C5—H5119.4N2—C29—H29A108.8
C5—C6—C7118.9 (7)C30—C29—H29B108.8
C5—C6—H6120.6N2—C29—H29B108.8
C7—C6—H6120.6H29A—C29—H29B107.7
C2—C7—C6120.3 (6)C35—C30—C31119.3 (6)
C2—C7—H7119.8C35—C30—C29120.6 (5)
C6—C7—H7119.8C31—C30—C29120.0 (6)
C9—C8—N1116.9 (4)C30—C31—C32119.8 (10)
C9—C8—H8A108.1C30—C31—H31120.1
N1—C8—H8A108.1C32—C31—H31120.1
C9—C8—H8B108.1C33—C32—C31120.5 (9)
N1—C8—H8B108.1C33—C32—H32119.7
H8A—C8—H8B107.3C31—C32—H32119.7
C10—C9—C14119.0 (6)C32—C33—C34120.7 (8)
C10—C9—C8120.9 (6)C32—C33—H33119.6
C14—C9—C8119.8 (6)C34—C33—H33119.6
C9—C10—C11120.6 (8)C33—C34—C35119.9 (10)
C9—C10—H10119.7C33—C34—H34120.0
C11—C10—H10119.7C35—C34—H34120.0
C12—C11—C10119.6 (8)C30—C35—C34119.7 (8)
C12—C11—H11120.2C30—C35—H35120.2
C10—C11—H11120.2C34—C35—H35120.2
C13—C12—C11119.7 (8)N2—C36—C37114.2 (4)
C13—C12—H12120.1N2—C36—H36A108.7
C11—C12—H12120.1C37—C36—H36A108.7
C12—C13—C14121.1 (8)N2—C36—H36B108.7
C12—C13—H13119.4C37—C36—H36B108.7
C14—C13—H13119.4H36A—C36—H36B107.6
C13—C14—C9119.8 (7)C38—C37—C42118.7 (5)
C13—C14—H14120.1C38—C37—C36120.9 (5)
C9—C14—H14120.1C42—C37—C36120.2 (5)
N1—C15—C16112.6 (4)C37—C38—C39119.6 (7)
N1—C15—H15A109.1C37—C38—H38120.2
C16—C15—H15A109.1C39—C38—H38120.2
N1—C15—H15B109.1C40—C39—C38121.3 (7)
C16—C15—H15B109.1C40—C39—H39119.3
H15A—C15—H15B107.8C38—C39—H39119.3
C17—C16—C21118.8 (5)C39—C40—C41119.8 (7)
C17—C16—C15122.0 (5)C39—C40—H40120.1
C21—C16—C15119.2 (5)C41—C40—H40120.1
C18—C17—C16120.3 (6)C40—C41—C42120.5 (7)
C18—C17—H17119.8C40—C41—H41119.8
C16—C17—H17119.8C42—C41—H41119.8
C17—C18—C19120.7 (6)C41—C42—C37120.0 (6)
C17—C18—H18119.6C41—C42—H42120.0
C19—C18—H18119.6C37—C42—H42120.0
C20—C19—C18118.9 (7)C15—N1—C8113.5 (4)
C20—C19—H19120.5C15—N1—C1111.6 (4)
C18—C19—H19120.5C8—N1—C1108.9 (4)
C19—C20—C21121.8 (7)C15—N1—H1C107.5
C19—C20—H20119.1C8—N1—H1C107.5
C21—C20—H20119.1C1—N1—H1C107.5
C20—C21—C16119.5 (6)C36—N2—C22111.4 (4)
C20—C21—H21120.3C36—N2—C29111.1 (4)
C16—C21—H21120.3C22—N2—C29111.0 (4)
C23—C22—N2114.7 (4)C36—N2—H2107.7
C23—C22—H22A108.6C22—N2—H2107.7
N2—C22—H22A108.6C29—N2—H2107.7
C23—C22—H22B108.6Cl3—Au1—Cl1177.75 (11)
N2—C22—H22B108.6Cl3—Au1—Cl489.38 (7)
H22A—C22—H22B107.6Cl1—Au1—Cl490.02 (8)
C28—C23—C24118.5 (5)Cl3—Au1—Cl290.38 (6)
C28—C23—C22120.7 (5)Cl1—Au1—Cl290.25 (8)
C24—C23—C22120.8 (5)Cl4—Au1—Cl2179.20 (6)
N1—C1—C2—C790.4 (6)C25—C26—C27—C28−1.3 (11)
N1—C1—C2—C3−91.2 (5)C24—C23—C28—C270.7 (9)
C7—C2—C3—C4−1.2 (8)C22—C23—C28—C27−179.9 (6)
C1—C2—C3—C4−179.6 (5)C26—C27—C28—C230.8 (10)
C2—C3—C4—C51.0 (9)N2—C29—C30—C3572.7 (7)
C3—C4—C5—C6−0.4 (11)N2—C29—C30—C31−111.4 (6)
C4—C5—C6—C7−0.1 (11)C35—C30—C31—C32−0.5 (11)
C3—C2—C7—C60.7 (8)C29—C30—C31—C32−176.4 (7)
C1—C2—C7—C6179.1 (5)C30—C31—C32—C330.0 (15)
C5—C6—C7—C2−0.1 (10)C31—C32—C33—C340.8 (17)
N1—C8—C9—C10−95.6 (7)C32—C33—C34—C35−1.0 (16)
N1—C8—C9—C1491.0 (6)C31—C30—C35—C340.3 (10)
C14—C9—C10—C11−2.8 (10)C29—C30—C35—C34176.1 (6)
C8—C9—C10—C11−176.2 (7)C33—C34—C35—C300.5 (13)
C9—C10—C11—C123.0 (14)N2—C36—C37—C38−94.3 (6)
C10—C11—C12—C13−2.3 (15)N2—C36—C37—C4290.9 (6)
C11—C12—C13—C141.5 (13)C42—C37—C38—C39−2.8 (9)
C12—C13—C14—C9−1.3 (10)C36—C37—C38—C39−177.8 (6)
C10—C9—C14—C131.9 (9)C37—C38—C39—C401.5 (11)
C8—C9—C14—C13175.4 (5)C38—C39—C40—C411.0 (12)
N1—C15—C16—C17−103.9 (6)C39—C40—C41—C42−2.1 (11)
N1—C15—C16—C2175.1 (6)C40—C41—C42—C370.6 (9)
C21—C16—C17—C18−1.6 (8)C38—C37—C42—C411.8 (8)
C15—C16—C17—C18177.5 (5)C36—C37—C42—C41176.8 (5)
C16—C17—C18—C190.7 (10)C16—C15—N1—C8−175.1 (4)
C17—C18—C19—C200.1 (12)C16—C15—N1—C161.4 (5)
C18—C19—C20—C210.1 (13)C9—C8—N1—C1554.6 (6)
C19—C20—C21—C16−1.0 (11)C9—C8—N1—C1179.6 (5)
C17—C16—C21—C201.7 (9)C2—C1—N1—C15−129.7 (5)
C15—C16—C21—C20−177.3 (6)C2—C1—N1—C8104.2 (5)
N2—C22—C23—C2885.7 (6)C37—C36—N2—C2263.1 (5)
N2—C22—C23—C24−94.9 (6)C37—C36—N2—C29−172.6 (4)
C28—C23—C24—C25−1.9 (8)C23—C22—N2—C36175.0 (4)
C22—C23—C24—C25178.7 (5)C23—C22—N2—C2950.7 (6)
C23—C24—C25—C261.5 (9)C30—C29—N2—C3654.2 (6)
C24—C25—C26—C270.1 (10)C30—C29—N2—C22178.8 (4)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N1—H1C···Cl50.912.193.089 (5)168
N2—H2···Cl5i0.912.163.066 (4)172

Symmetry codes: (i) −x, −y+1, −z+1.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB5291).

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