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Acta Crystallogr Sect E Struct Rep Online. 2009 December 1; 65(Pt 12): m1570.
Published online 2009 November 14. doi:  10.1107/S1600536809047084
PMCID: PMC2971935

[(Z)-N,O-Disopropyl­thio­carbamato-κS](tricyclo­hexyl­phosphine-κP)gold(I)

Abstract

In the title compound, [Au(C7H14NOS)(C18H33P)], the AuI atom is coordinated within an S,P-donor set that defines a slightly distorted linear geometry [S—Au—P = 174.94 (2)°], with the distortion due to a short intra­molecular Au(...)O contact [2.908 (2) Å].

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]).

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Object name is e-65-m1570-scheme1.jpg

Experimental

Crystal data

  • [Au(C7H14NOS)(C18H33P)]
  • M r = 637.63
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-m1570-efi1.jpg
  • a = 11.1236 (5) Å
  • b = 11.7949 (6) Å
  • c = 11.9037 (6) Å
  • α = 73.869 (1)°
  • β = 85.282 (1)°
  • γ = 66.515 (1)°
  • V = 1375.30 (12) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 5.50 mm−1
  • T = 223 K
  • 0.19 × 0.16 × 0.11 mm

Data collection

  • Bruker SMART CCD diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2000 [triangle]) T min = 0.636, T max = 1
  • 10973 measured reflections
  • 6300 independent reflections
  • 5853 reflections with I > 2σ(I)
  • R int = 0.020

Refinement

  • R[F 2 > 2σ(F 2)] = 0.021
  • wR(F 2) = 0.054
  • S = 0.98
  • 6300 reflections
  • 271 parameters
  • H-atom parameters constrained
  • Δρmax = 1.01 e Å−3
  • Δρmin = −0.78 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: SHELXL97.

Table 1
Selected bond lengths (Å)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809047084/hb5218sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809047084/hb5218Isup2.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 an on-going study of the structural systematics of molecules related to the general formula R3PAu[SC(OR')NR''] for R, R' and R'' = alkyl and aryl (Ho et al. 2006; Ho & Tiekink, 2007; Kuan et al., 2008), the title compound, (I), was investigated.

In keeping with previous studies, the gold atom exists within an SP donor set defined by the phosphine-P and thiolate-S atoms, Table 1 and Fig. 1. Confirmation that the carbonimidothioate ligand is functioning as a thiolate is found in the magnitudes of the C1—S1 and C1═N1 distances of 1.767 (3) and 1.263 (3) Å, respectively. The coordination geometry is distorted from the ideal linear [S—Au—P = 174.94 (2) °] owing to the close approach of the O1 atom, 2.908 (2) Å.

Experimental

Compound (I) was prepared following the standard literature procedure from the reaction of Cy3PAuCl and (iPr)OC(S)N(H)(iPr) in the presence of base (Hall et al., 1993).

Refinement

The H atoms were geometrically placed (C—H = 0.97–0.99 Å) and refined as riding with Uiso(H) = 1.2–1.5Ueq(C). The maximum and minimum residual electron density peaks of 1.01 and 0.78 e Å-3, respectively, were located 0.92 Å and 0.83 Å from the Au atom.

Figures

Fig. 1.
Molecular structure of (I) showing displacement ellipsoids at the 50% probability level.

Crystal data

[Au(C7H14NOS)(C18H33P)]Z = 2
Mr = 637.63F(000) = 644
Triclinic, P1Dx = 1.540 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71069 Å
a = 11.1236 (5) ÅCell parameters from 7451 reflections
b = 11.7949 (6) Åθ = 2.2–30.0°
c = 11.9037 (6) ŵ = 5.50 mm1
α = 73.869 (1)°T = 223 K
β = 85.282 (1)°Block, colourless
γ = 66.515 (1)°0.19 × 0.16 × 0.11 mm
V = 1375.30 (12) Å3

Data collection

Bruker SMART CCD diffractometer6300 independent reflections
Radiation source: fine-focus sealed tube5853 reflections with I > 2σ(I)
graphiteRint = 0.020
ω scansθmax = 27.5°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2000)h = −14→14
Tmin = 0.636, Tmax = 1k = −15→15
10973 measured reflectionsl = −13→15

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)] = 0.021Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.054H-atom parameters constrained
S = 0.98w = 1/[σ2(Fo2) + (0.0323P)2] where P = (Fo2 + 2Fc2)/3
6300 reflections(Δ/σ)max = 0.001
271 parametersΔρmax = 1.01 e Å3
0 restraintsΔρmin = −0.78 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
Au0.099579 (9)0.244875 (8)−0.000750 (8)0.02575 (4)
S10.17603 (7)0.13648 (7)0.18959 (6)0.03236 (15)
P10.04149 (6)0.33925 (6)−0.19218 (6)0.02396 (13)
O10.30086 (19)−0.01420 (18)0.05751 (16)0.0341 (4)
N10.3452 (2)−0.1149 (2)0.2521 (2)0.0380 (6)
C10.2845 (3)−0.0148 (3)0.1727 (2)0.0302 (6)
C20.3294 (3)−0.1112 (3)0.3740 (3)0.0452 (8)
H20.2426−0.04460.38200.054*
C30.4361 (4)−0.0765 (4)0.4098 (3)0.0602 (10)
H3A0.42760.00760.36140.090*
H3B0.5216−0.13970.39960.090*
H3C0.4270−0.07530.49130.090*
C40.3361 (4)−0.2409 (4)0.4495 (3)0.0616 (11)
H4A0.2668−0.25970.42470.092*
H4B0.3253−0.23910.53070.092*
H4C0.4205−0.30680.44120.092*
C50.3930 (3)−0.1300 (3)0.0295 (3)0.0385 (7)
H50.4687−0.17220.08590.046*
C60.3260 (4)−0.2196 (4)0.0361 (4)0.0618 (11)
H6A0.2994−0.24530.11560.093*
H6B0.3860−0.29500.01330.093*
H6C0.2494−0.1766−0.01630.093*
C70.4384 (3)−0.0863 (3)−0.0916 (3)0.0458 (7)
H7A0.4820−0.0298−0.09090.069*
H7B0.3634−0.0407−0.14590.069*
H7C0.4992−0.1604−0.11590.069*
C80.0941 (3)0.2106 (3)−0.2671 (2)0.0301 (5)
H80.19050.1670−0.25450.036*
C90.0396 (4)0.1087 (3)−0.2087 (3)0.0438 (7)
H9A−0.05620.1465−0.21850.053*
H9B0.06190.0785−0.12470.053*
C100.0966 (4)−0.0041 (3)−0.2628 (4)0.0544 (9)
H10A0.1909−0.0483−0.24370.065*
H10B0.0556−0.0651−0.22870.065*
C110.0755 (4)0.0378 (4)−0.3945 (4)0.0631 (11)
H11A0.1189−0.0367−0.42580.076*
H11B−0.01860.0722−0.41360.076*
C120.1290 (5)0.1389 (4)−0.4514 (3)0.0652 (11)
H12A0.10840.1682−0.53570.078*
H12B0.22460.1018−0.44010.078*
C130.0697 (4)0.2527 (3)−0.3988 (3)0.0509 (8)
H13A0.10830.3154−0.43440.061*
H13B−0.02490.2944−0.41640.061*
C140.1314 (2)0.4419 (2)−0.2571 (2)0.0274 (5)
H140.10620.4802−0.34130.033*
C150.2799 (3)0.3628 (3)−0.2449 (3)0.0393 (7)
H15A0.30390.3165−0.16260.047*
H15B0.30280.2992−0.28970.047*
C160.3585 (3)0.4462 (3)−0.2882 (3)0.0469 (8)
H16A0.45220.3926−0.27360.056*
H16B0.34320.4840−0.37280.056*
C170.3205 (3)0.5522 (3)−0.2277 (3)0.0471 (8)
H17A0.36870.6069−0.26090.057*
H17B0.34500.5144−0.14430.057*
C180.1739 (3)0.6335 (3)−0.2416 (3)0.0449 (8)
H18A0.15080.6788−0.32430.054*
H18B0.15150.6978−0.19760.054*
C190.0950 (3)0.5502 (3)−0.1972 (3)0.0345 (6)
H19A0.00130.6042−0.21140.041*
H19B0.11060.5129−0.11260.041*
C20−0.1345 (2)0.4342 (2)−0.2282 (2)0.0276 (5)
H20−0.17230.3730−0.23460.033*
C21−0.2064 (3)0.4929 (3)−0.1287 (2)0.0329 (6)
H21A−0.19260.4245−0.05590.039*
H21B−0.16980.5519−0.11670.039*
C22−0.3537 (3)0.5655 (3)−0.1575 (3)0.0438 (7)
H22A−0.39200.5046−0.16030.053*
H22B−0.39570.6063−0.09530.053*
C23−0.3806 (3)0.6671 (3)−0.2735 (3)0.0418 (7)
H23A−0.47540.7097−0.29040.050*
H23B−0.34850.7320−0.26900.050*
C24−0.3136 (3)0.6074 (3)−0.3709 (3)0.0467 (8)
H24A−0.33050.6745−0.44500.056*
H24B−0.34990.5466−0.37870.056*
C25−0.1655 (3)0.5375 (3)−0.3458 (3)0.0378 (7)
H25A−0.12830.5997−0.34430.045*
H25B−0.12460.4974−0.40860.045*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Au0.02761 (6)0.01936 (6)0.02462 (6)−0.00442 (4)−0.00234 (4)−0.00356 (4)
S10.0360 (4)0.0243 (3)0.0259 (3)−0.0015 (3)−0.0027 (3)−0.0044 (3)
P10.0252 (3)0.0187 (3)0.0247 (3)−0.0053 (3)−0.0015 (2)−0.0049 (2)
O10.0358 (10)0.0254 (10)0.0282 (10)−0.0006 (8)0.0011 (8)−0.0048 (8)
N10.0385 (13)0.0281 (13)0.0303 (13)0.0008 (11)0.0010 (10)−0.0025 (10)
C10.0285 (13)0.0268 (14)0.0289 (14)−0.0059 (11)0.0021 (10)−0.0054 (11)
C20.0455 (18)0.0347 (17)0.0309 (16)0.0037 (14)0.0022 (13)−0.0008 (13)
C30.064 (2)0.058 (2)0.044 (2)−0.011 (2)−0.0136 (17)−0.0071 (17)
C40.064 (2)0.044 (2)0.046 (2)−0.0061 (18)0.0062 (17)0.0104 (16)
C50.0369 (15)0.0297 (15)0.0375 (16)−0.0022 (13)0.0065 (12)−0.0097 (12)
C60.084 (3)0.041 (2)0.062 (3)−0.029 (2)0.030 (2)−0.0193 (18)
C70.0444 (18)0.0478 (19)0.0451 (19)−0.0154 (16)0.0150 (14)−0.0201 (15)
C80.0338 (14)0.0249 (13)0.0318 (14)−0.0083 (11)0.0003 (11)−0.0126 (11)
C90.058 (2)0.0347 (17)0.0484 (19)−0.0249 (16)0.0116 (15)−0.0194 (14)
C100.061 (2)0.0403 (19)0.078 (3)−0.0250 (18)0.0040 (19)−0.0323 (19)
C110.059 (2)0.062 (2)0.080 (3)−0.012 (2)−0.006 (2)−0.052 (2)
C120.094 (3)0.058 (2)0.042 (2)−0.018 (2)0.0045 (19)−0.0297 (18)
C130.072 (2)0.0406 (18)0.0328 (17)−0.0105 (17)−0.0007 (15)−0.0158 (14)
C140.0288 (13)0.0221 (12)0.0286 (13)−0.0088 (11)−0.0002 (10)−0.0043 (10)
C150.0294 (14)0.0299 (15)0.0532 (19)−0.0065 (12)0.0039 (12)−0.0112 (13)
C160.0291 (15)0.0450 (19)0.061 (2)−0.0141 (14)0.0047 (14)−0.0079 (16)
C170.0380 (17)0.0453 (19)0.062 (2)−0.0241 (16)0.0003 (15)−0.0093 (16)
C180.0431 (17)0.0322 (16)0.063 (2)−0.0198 (15)0.0036 (15)−0.0102 (15)
C190.0337 (14)0.0280 (14)0.0434 (17)−0.0125 (12)0.0055 (12)−0.0127 (12)
C200.0252 (12)0.0233 (13)0.0297 (14)−0.0053 (10)−0.0047 (10)−0.0046 (10)
C210.0297 (14)0.0304 (14)0.0325 (15)−0.0060 (12)0.0000 (11)−0.0075 (11)
C220.0282 (15)0.0349 (17)0.057 (2)−0.0050 (13)0.0057 (13)−0.0063 (14)
C230.0271 (14)0.0313 (16)0.056 (2)−0.0050 (12)−0.0045 (13)−0.0038 (14)
C240.0392 (17)0.0387 (18)0.0473 (19)−0.0044 (14)−0.0180 (14)0.0003 (14)
C250.0351 (15)0.0366 (16)0.0298 (15)−0.0056 (13)−0.0067 (12)−0.0012 (12)

Geometric parameters (Å, °)

Au—S12.3091 (7)C12—C131.524 (5)
Au—P12.2602 (7)C12—H12A0.9800
S1—C11.767 (3)C12—H12B0.9800
P1—C201.842 (3)C13—H13A0.9800
P1—C141.839 (2)C13—H13B0.9800
P1—C81.844 (3)C14—C191.532 (4)
O1—C11.367 (3)C14—C151.535 (4)
O1—C51.452 (3)C14—H140.9900
N1—C11.263 (3)C15—C161.525 (4)
N1—C21.458 (4)C15—H15A0.9800
C2—C41.520 (4)C15—H15B0.9800
C2—C31.524 (5)C16—C171.513 (5)
C2—H20.9900C16—H16A0.9800
C3—H3A0.9700C16—H16B0.9800
C3—H3B0.9700C17—C181.522 (4)
C3—H3C0.9700C17—H17A0.9800
C4—H4A0.9700C17—H17B0.9800
C4—H4B0.9700C18—C191.529 (4)
C4—H4C0.9700C18—H18A0.9800
C5—C71.508 (4)C18—H18B0.9800
C5—C61.500 (5)C19—H19A0.9800
C5—H50.9900C19—H19B0.9800
C6—H6A0.9700C20—C251.536 (4)
C6—H6B0.9700C20—C211.543 (4)
C6—H6C0.9700C20—H200.9900
C7—H7A0.9700C21—C221.531 (4)
C7—H7B0.9700C21—H21A0.9800
C7—H7C0.9700C21—H21B0.9800
C8—C131.519 (4)C22—C231.515 (4)
C8—C91.530 (4)C22—H22A0.9800
C8—H80.9900C22—H22B0.9800
C9—C101.525 (5)C23—C241.512 (5)
C9—H9A0.9800C23—H23A0.9800
C9—H9B0.9800C23—H23B0.9800
C10—C111.514 (6)C24—C251.532 (4)
C10—H10A0.9800C24—H24A0.9800
C10—H10B0.9800C24—H24B0.9800
C11—C121.512 (6)C25—H25A0.9800
C11—H11A0.9800C25—H25B0.9800
C11—H11B0.9800
P1—Au—S1174.94 (2)C8—C13—C12111.3 (3)
C1—S1—Au101.17 (9)C8—C13—H13A109.4
C20—P1—C14108.31 (12)C12—C13—H13A109.4
C20—P1—C8106.97 (12)C8—C13—H13B109.4
C14—P1—C8106.64 (12)C12—C13—H13B109.4
C20—P1—Au116.82 (9)H13A—C13—H13B108.0
C14—P1—Au110.30 (9)C19—C14—C15110.1 (2)
C8—P1—Au107.28 (9)C19—C14—P1109.76 (18)
C1—O1—C5118.2 (2)C15—C14—P1110.57 (18)
C1—N1—C2119.2 (3)C19—C14—H14108.8
N1—C1—O1120.5 (3)C15—C14—H14108.8
N1—C1—S1127.7 (2)P1—C14—H14108.8
O1—C1—S1111.82 (18)C16—C15—C14112.3 (2)
N1—C2—C4109.0 (3)C16—C15—H15A109.1
N1—C2—C3109.0 (3)C14—C15—H15A109.1
C4—C2—C3111.7 (3)C16—C15—H15B109.1
N1—C2—H2109.0C14—C15—H15B109.1
C4—C2—H2109.0H15A—C15—H15B107.9
C3—C2—H2109.0C17—C16—C15111.5 (3)
C2—C3—H3A109.5C17—C16—H16A109.3
C2—C3—H3B109.5C15—C16—H16A109.3
H3A—C3—H3B109.5C17—C16—H16B109.3
C2—C3—H3C109.5C15—C16—H16B109.3
H3A—C3—H3C109.5H16A—C16—H16B108.0
H3B—C3—H3C109.5C16—C17—C18111.4 (3)
C2—C4—H4A109.5C16—C17—H17A109.3
C2—C4—H4B109.5C18—C17—H17A109.3
H4A—C4—H4B109.5C16—C17—H17B109.3
C2—C4—H4C109.5C18—C17—H17B109.3
H4A—C4—H4C109.5H17A—C17—H17B108.0
H4B—C4—H4C109.5C17—C18—C19110.9 (3)
O1—C5—C7105.7 (2)C17—C18—H18A109.5
O1—C5—C6109.4 (3)C19—C18—H18A109.5
C7—C5—C6112.7 (3)C17—C18—H18B109.5
O1—C5—H5109.6C19—C18—H18B109.5
C7—C5—H5109.6H18A—C18—H18B108.0
C6—C5—H5109.6C18—C19—C14112.2 (2)
C5—C6—H6A109.5C18—C19—H19A109.2
C5—C6—H6B109.5C14—C19—H19A109.2
H6A—C6—H6B109.5C18—C19—H19B109.2
C5—C6—H6C109.5C14—C19—H19B109.2
H6A—C6—H6C109.5H19A—C19—H19B107.9
H6B—C6—H6C109.5C25—C20—C21110.5 (2)
C5—C7—H7A109.5C25—C20—P1114.90 (18)
C5—C7—H7B109.5C21—C20—P1111.93 (17)
H7A—C7—H7B109.5C25—C20—H20106.3
C5—C7—H7C109.5C21—C20—H20106.3
H7A—C7—H7C109.5P1—C20—H20106.3
H7B—C7—H7C109.5C22—C21—C20111.2 (2)
C13—C8—C9111.0 (3)C22—C21—H21A109.4
C13—C8—P1116.5 (2)C20—C21—H21A109.4
C9—C8—P1111.1 (2)C22—C21—H21B109.4
C13—C8—H8105.8C20—C21—H21B109.4
C9—C8—H8105.8H21A—C21—H21B108.0
P1—C8—H8105.8C23—C22—C21111.7 (2)
C8—C9—C10110.3 (3)C23—C22—H22A109.3
C8—C9—H9A109.6C21—C22—H22A109.3
C10—C9—H9A109.6C23—C22—H22B109.3
C8—C9—H9B109.6C21—C22—H22B109.3
C10—C9—H9B109.6H22A—C22—H22B107.9
H9A—C9—H9B108.1C24—C23—C22110.5 (3)
C11—C10—C9112.2 (3)C24—C23—H23A109.5
C11—C10—H10A109.2C22—C23—H23A109.5
C9—C10—H10A109.2C24—C23—H23B109.5
C11—C10—H10B109.2C22—C23—H23B109.5
C9—C10—H10B109.2H23A—C23—H23B108.1
H10A—C10—H10B107.9C23—C24—C25110.8 (3)
C12—C11—C10111.6 (3)C23—C24—H24A109.5
C12—C11—H11A109.3C25—C24—H24A109.5
C10—C11—H11A109.3C23—C24—H24B109.5
C12—C11—H11B109.3C25—C24—H24B109.5
C10—C11—H11B109.3H24A—C24—H24B108.1
H11A—C11—H11B108.0C24—C25—C20111.3 (2)
C11—C12—C13110.6 (3)C24—C25—H25A109.4
C11—C12—H12A109.5C20—C25—H25A109.4
C13—C12—H12A109.5C24—C25—H25B109.4
C11—C12—H12B109.5C20—C25—H25B109.4
C13—C12—H12B109.5H25A—C25—H25B108.0
H12A—C12—H12B108.1
C2—N1—C1—O1177.8 (2)Au—P1—C14—C19−62.62 (19)
C2—N1—C1—S1−0.8 (4)C20—P1—C14—C15−172.0 (2)
C5—O1—C1—N1−2.1 (4)C8—P1—C14—C15−57.1 (2)
C5—O1—C1—S1176.71 (19)Au—P1—C14—C1559.0 (2)
Au—S1—C1—N1−173.7 (2)C19—C14—C15—C16−53.6 (3)
Au—S1—C1—O17.64 (19)P1—C14—C15—C16−175.1 (2)
C1—N1—C2—C4146.0 (3)C14—C15—C16—C1755.0 (4)
C1—N1—C2—C3−91.8 (3)C15—C16—C17—C18−55.6 (4)
C1—O1—C5—C7−153.8 (2)C16—C17—C18—C1955.7 (4)
C1—O1—C5—C684.5 (3)C17—C18—C19—C14−55.6 (4)
C20—P1—C8—C1356.3 (3)C15—C14—C19—C1854.1 (3)
C14—P1—C8—C13−59.4 (3)P1—C14—C19—C18176.0 (2)
Au—P1—C8—C13−177.6 (2)C14—P1—C20—C2531.2 (2)
C20—P1—C8—C9−72.0 (2)C8—P1—C20—C25−83.4 (2)
C14—P1—C8—C9172.2 (2)Au—P1—C20—C25156.48 (18)
Au—P1—C8—C954.1 (2)C14—P1—C20—C21−95.9 (2)
C13—C8—C9—C1055.2 (4)C8—P1—C20—C21149.53 (18)
P1—C8—C9—C10−173.5 (2)Au—P1—C20—C2129.4 (2)
C8—C9—C10—C11−54.5 (4)C25—C20—C21—C2253.5 (3)
C9—C10—C11—C1255.0 (4)P1—C20—C21—C22−177.03 (19)
C10—C11—C12—C13−55.3 (5)C20—C21—C22—C23−55.3 (3)
C9—C8—C13—C12−57.0 (4)C21—C22—C23—C2457.4 (4)
P1—C8—C13—C12174.6 (3)C22—C23—C24—C25−58.0 (3)
C11—C12—C13—C856.6 (4)C23—C24—C25—C2057.3 (4)
C20—P1—C14—C1966.4 (2)C21—C20—C25—C24−54.7 (3)
C8—P1—C14—C19−178.80 (19)P1—C20—C25—C24177.5 (2)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB5218).

References

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