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Acta Crystallogr Sect E Struct Rep Online. 2008 January 1; 64(Pt 1): o184.
Published online 2007 December 6. doi:  10.1107/S1600536807063945
PMCID: PMC2915247

1,5,6-Triphenyl-8-oxa-7-selena-6-phos­phabicyclo­[3.2.1]octane-6-selone

Abstract

The structure of the title compound, C23H21OPSe2, consists of fused puckered five- and six-membered rings, PSeC2O and C5O, respectively, with a C2O bridgehead. The C5O ring adopts a chair conformation, whilst the C2PSeO ring has an envelope conformation.

Related literature

For related literature, see: An et al. (1998 [triangle]); Bhattacharyya et al. (2000 [triangle], 2001a [triangle],b [triangle], 2002 [triangle]); Fitzmaurice et al. (1988 [triangle]); Gray, Bhattacharyya et al. (2005 [triangle]), Gray, Slawin et al. (2005 [triangle]); Hua & Woollins (2007 [triangle]); Hua, Li et al. (2006 [triangle], 2007a [triangle],b [triangle],c [triangle]); Shi et al. (2006 [triangle], 2007 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-0o184-scheme1.jpg

Experimental

Crystal data

  • C23H21OPSe2
  • M r = 502.29
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-0o184-efi1.jpg
  • a = 7.6802 (9) Å
  • b = 9.0613 (12) Å
  • c = 14.9070 (16) Å
  • α = 84.949 (8)°
  • β = 75.677 (7)°
  • γ = 89.266 (8)°
  • V = 1001.2 (2) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 3.78 mm−1
  • T = 93 (2) K
  • 0.20 × 0.20 × 0.15 mm

Data collection

  • Rigaku Mercury CCD diffractometer
  • Absorption correction: multi-scan (CrystalClear; Rigaku, 2004 [triangle]) T min = 0.489, T max = 0.570
  • 7092 measured reflections
  • 3805 independent reflections
  • 3000 reflections with I > 2σ(I)
  • R int = 0.031

Refinement

  • R[F 2 > 2σ(F 2)] = 0.039
  • wR(F 2) = 0.072
  • S = 1.00
  • 3805 reflections
  • 244 parameters
  • H-atom parameters constrained
  • Δρmax = 0.85 e Å−3
  • Δρmin = −0.82 e Å−3

Data collection: CrystalClear (Rigaku, 2004 [triangle]); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997 [triangle]); molecular graphics: SHELXTL (Sheldrick,2003 [triangle]); software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536807063945/pv2051sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807063945/pv2051Isup2.hkl

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

Acknowledgments

The authors are grateful to the Engineering and Physical Science Research Council (EPSRC, UK) for financial support.

supplementary crystallographic information

Comment

2,4-bis(phenyl)-1,3-diselenadiphosphetane-2,4-diselenide (PhPSe2)2, also known as Woollins reagent, WR, is a selenium analogue of the well known Lawessons reagent, (p-MeOPhPS2)2. WR has found applications in the synthesis of selenium containing organic molecules, P—Se containing heterocycles and related compounds (Gray, Bhattacharyya et al.., 2005; Gray, Slawin et al.., 2005, Shi et al., 2006, 2007, Bhattacharyya et al. 2000, 2001a, 2001b, 2002, Hua, Li et al. 2006, 2007a, 2007b, 2007c). We report here the synthesis and X-ray structure of a new fused [3,2,1] ring P—Se heterocycle. The title compound, (I), was generated by the reaction of Woollins' reagent with 1,4-diketone. The P = Se bond length (2.0995 (9) Å) and the P – Se distance (2.2278 (10) Å) are consistent with the related selenides-containing PV= Se bonds (2.08 – 2.12 Å) and PV—Se single bonds (Fitzmaurice et al. 1988, An et al. 1998).

Experimental

A red suspension of 1,3-dibenzoylpropane (0.25 g, 1 mmol) and Woollins' reagent (0.54 g, 1 mmol) in dry toluene (10 ml) was refluxed for 16 hr. The yellow suspension was formed along with small amount of grey elemental selenium. Upon cooling to room temperature the mixture was purified by silica gel chromatography (1:9 ethyl acetate/dichloromethane as eluent) to give the title compound in 20% yield. Crystals were obtained from dichloromethane/hexane by diffusion method.

Refinement

All H atoms were included in calculated positions (C—H distances are 0.98 Å for methyl H atoms, 0.99 Å for methylene H atoms and 0.95 Å for aryl H atoms) and were included in the refinement as riding atoms with Uĩso~(H) = 1.2 U~eq~ (parent atom, methylene and aryl H atoms) or Uĩso~(H) = 1.5 U~eq~ (parent atom, methyl H atoms).

Figures

Fig. 1.
The structure of (I) with displacement ellipsoids drawn at the 50% probability level; H-atoms have been ignored for clarity.

Crystal data

C23H21OPSe2Z = 2
Mr = 502.29F000 = 500
Triclinic, P1Dx = 1.666 Mg m3
Hall symbol: -P 1Mo Kα radiation λ = 0.71073 Å
a = 7.6802 (9) ÅCell parameters from 3344 reflections
b = 9.0613 (12) Åθ = 2.3–28.4º
c = 14.9070 (16) ŵ = 3.78 mm1
α = 84.949 (8)ºT = 93 (2) K
β = 75.677 (7)ºBlock, colorless
γ = 89.266 (8)º0.20 × 0.20 × 0.15 mm
V = 1001.2 (2) Å3

Data collection

Rigaku Mercury CCD diffractometer3805 independent reflections
Radiation source: rotating anode3000 reflections with I > 2σ(I)
Monochromator: confocalRint = 0.031
T = 93(2) Kθmax = 25.8º
ω and [var phi] scansθmin = 2.3º
Absorption correction: multi-scan(CrystalClear; Rigaku, 2004)h = −10→9
Tmin = 0.489, Tmax = 0.570k = −10→10
7092 measured reflectionsl = −15→19

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.039H-atom parameters constrained
wR(F2) = 0.072  w = 1/[σ2(Fo2) + (0.0278P)2] where P = (Fo2 + 2Fc2)/3
S = 1.00(Δ/σ)max = 0.001
3805 reflectionsΔρmax = 0.85 e Å3
244 parametersΔρmin = −0.82 e Å3
Primary atom site location: structure-invariant direct methodsExtinction correction: none

Special details

Experimental. Anal. Calcd for C23H21OPSe2: C, 55.00; H, 4.21. Found: C, 54.86; H, 4.15. 1H NMR (CDCl3): 7.72–7.05 (m, 15H, ArH), 2.37 (m, 4H, CH2), 1.25 (m, 2H, CH2). 31P NMR (CDCl3): 79.23 (s, J(P,Seendo) = 430 Hz, J(P,Seexo) = 776 Hz). 77Se NMR (CDCl3): 34.61 (d, J(P,Seendo) = 430 Hz), -94.02 (d, J(P,Seexo) = 778 Hz).
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
C20.3921 (4)0.3495 (4)0.1438 (2)0.0194 (8)
H20.30590.41060.17990.023*
Se20.56063 (4)0.04366 (4)0.35534 (2)0.01561 (11)
Se10.26388 (4)0.37283 (4)0.37994 (2)0.01944 (11)
P10.49881 (10)0.27352 (10)0.30698 (6)0.0137 (2)
O10.8475 (3)0.2463 (2)0.29505 (14)0.0147 (5)
C100.8065 (4)0.1527 (4)0.4568 (2)0.0163 (8)
H10A0.92830.18260.45980.020*
H10B0.77100.06250.49990.020*
C180.9461 (4)0.0000 (4)0.3233 (2)0.0161 (8)
C10.5138 (4)0.2689 (4)0.1839 (2)0.0151 (7)
C120.7708 (4)0.4895 (4)0.2422 (2)0.0133 (7)
C110.8112 (4)0.1176 (4)0.3592 (2)0.0159 (8)
C80.7048 (4)0.4071 (4)0.4139 (2)0.0167 (8)
H8A0.60440.47730.42990.020*
H8B0.81700.45960.41400.020*
C60.6430 (4)0.1821 (4)0.1293 (2)0.0176 (8)
H60.72760.12850.15600.021*
C170.6750 (4)0.6216 (4)0.2523 (2)0.0180 (8)
H170.57530.62890.30410.022*
C40.5238 (5)0.2527 (4)−0.0025 (2)0.0275 (9)
H40.52620.2462−0.06600.033*
C50.6475 (4)0.1744 (4)0.0366 (2)0.0229 (9)
H50.73530.1155−0.00040.027*
C211.1979 (4)−0.2146 (4)0.2626 (2)0.0217 (9)
H211.2835−0.28830.24120.026*
C90.6751 (4)0.2765 (4)0.4882 (2)0.0165 (8)
H9A0.69230.30960.54700.020*
H9B0.55030.23890.49980.020*
C160.7245 (4)0.7418 (4)0.1872 (2)0.0207 (8)
H160.65820.83100.19420.025*
C221.0516 (4)−0.2490 (4)0.3370 (2)0.0228 (9)
H221.0371−0.34650.36720.027*
C140.9652 (4)0.6018 (4)0.1018 (2)0.0217 (8)
H141.06550.59540.05010.026*
C191.0923 (4)0.0345 (4)0.2492 (2)0.0203 (8)
H191.10630.13160.21840.024*
C30.3977 (4)0.3398 (4)0.0505 (2)0.0263 (9)
H30.31410.39360.02320.032*
C230.9267 (4)−0.1415 (4)0.3674 (2)0.0212 (8)
H230.8271−0.16520.41870.025*
C70.7176 (4)0.3607 (4)0.3169 (2)0.0134 (7)
C130.9160 (4)0.4807 (4)0.1661 (2)0.0182 (8)
H130.98170.39130.15820.022*
C150.8693 (4)0.7326 (4)0.1122 (2)0.0231 (9)
H150.90350.81540.06780.028*
C201.2179 (4)−0.0732 (4)0.2201 (2)0.0222 (9)
H201.3195−0.04880.17000.027*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C20.0152 (17)0.022 (2)0.0206 (19)0.0026 (15)−0.0049 (15)0.0004 (15)
Se20.01333 (18)0.0149 (2)0.0184 (2)−0.00064 (13)−0.00467 (15)0.00179 (14)
Se10.01320 (18)0.0222 (2)0.0215 (2)0.00329 (14)−0.00123 (15)−0.00340 (15)
P10.0122 (4)0.0142 (5)0.0143 (4)0.0011 (3)−0.0029 (4)−0.0009 (4)
O10.0150 (11)0.0130 (14)0.0160 (12)0.0019 (9)−0.0046 (10)0.0014 (10)
C100.0132 (16)0.022 (2)0.0150 (17)−0.0037 (14)−0.0056 (14)0.0009 (14)
C180.0137 (17)0.017 (2)0.0194 (18)0.0013 (14)−0.0081 (16)−0.0017 (15)
C10.0130 (16)0.015 (2)0.0170 (18)−0.0060 (14)−0.0038 (15)0.0000 (14)
C120.0148 (17)0.013 (2)0.0144 (17)−0.0021 (13)−0.0074 (15)0.0001 (14)
C110.0109 (16)0.015 (2)0.0220 (19)0.0024 (14)−0.0047 (15)−0.0018 (15)
C80.0149 (16)0.021 (2)0.0146 (17)−0.0017 (14)−0.0035 (15)−0.0047 (15)
C60.0141 (17)0.022 (2)0.0169 (18)0.0010 (15)−0.0032 (15)−0.0030 (15)
C170.0168 (17)0.020 (2)0.0191 (18)0.0008 (15)−0.0074 (15)−0.0034 (15)
C40.029 (2)0.041 (3)0.0137 (19)−0.0014 (18)−0.0080 (17)−0.0025 (17)
C50.0192 (18)0.028 (2)0.0196 (19)0.0014 (16)−0.0011 (16)−0.0051 (16)
C210.0178 (18)0.023 (2)0.027 (2)0.0077 (15)−0.0098 (17)−0.0090 (16)
C90.0174 (17)0.019 (2)0.0137 (17)0.0009 (14)−0.0047 (15)−0.0009 (14)
C160.0237 (19)0.014 (2)0.025 (2)0.0037 (15)−0.0079 (17)−0.0016 (15)
C220.026 (2)0.016 (2)0.030 (2)0.0033 (15)−0.0160 (18)0.0037 (16)
C140.0199 (18)0.025 (2)0.0171 (18)0.0008 (16)−0.0005 (16)0.0013 (15)
C190.0184 (18)0.016 (2)0.025 (2)0.0001 (15)−0.0035 (16)0.0009 (15)
C30.027 (2)0.032 (3)0.023 (2)0.0042 (17)−0.0144 (18)0.0028 (17)
C230.0163 (17)0.025 (2)0.0233 (19)0.0024 (15)−0.0087 (16)0.0031 (16)
C70.0094 (15)0.012 (2)0.0198 (18)0.0029 (13)−0.0047 (14)−0.0054 (14)
C130.0149 (17)0.019 (2)0.0201 (18)0.0013 (15)−0.0033 (16)−0.0024 (15)
C150.026 (2)0.021 (2)0.0215 (19)−0.0041 (16)−0.0064 (17)0.0048 (16)
C200.0136 (17)0.022 (2)0.028 (2)0.0002 (15)0.0006 (16)−0.0033 (16)

Geometric parameters (Å, °)

C2—C31.391 (5)C6—H60.9500
C2—C11.395 (4)C17—C161.384 (5)
C2—H20.9500C17—H170.9500
Se2—C112.062 (3)C4—C31.377 (5)
Se2—P12.2278 (10)C4—C51.389 (5)
Se1—P12.0995 (9)C4—H40.9500
P1—C11.814 (3)C5—H50.9500
P1—C71.909 (3)C21—C201.371 (5)
O1—C111.425 (4)C21—C221.387 (5)
O1—C71.432 (3)C21—H210.9500
C10—C111.509 (4)C9—H9A0.9900
C10—C91.525 (4)C9—H9B0.9900
C10—H10A0.9900C16—C151.375 (4)
C10—H10B0.9900C16—H160.9500
C18—C231.381 (5)C22—C231.383 (5)
C18—C191.384 (4)C22—H220.9500
C18—C111.514 (4)C14—C131.383 (4)
C1—C61.400 (4)C14—C151.387 (5)
C12—C131.387 (4)C14—H140.9500
C12—C171.396 (4)C19—C201.383 (4)
C12—C71.525 (4)C19—H190.9500
C8—C71.521 (4)C3—H30.9500
C8—C91.526 (4)C23—H230.9500
C8—H8A0.9900C13—H130.9500
C8—H8B0.9900C15—H150.9500
C6—C51.381 (4)C20—H200.9500
C3—C2—C1119.6 (3)C5—C4—H4119.9
C3—C2—H2120.2C6—C5—C4120.1 (3)
C1—C2—H2120.2C6—C5—H5120.0
C11—Se2—P188.68 (9)C4—C5—H5120.0
C1—P1—C7106.71 (14)C20—C21—C22119.4 (3)
C1—P1—Se1113.82 (10)C20—C21—H21120.3
C7—P1—Se1114.85 (10)C22—C21—H21120.3
C1—P1—Se2105.00 (11)C10—C9—C8110.4 (3)
C7—P1—Se295.97 (10)C10—C9—H9A109.6
Se1—P1—Se2118.47 (4)C8—C9—H9A109.6
C11—O1—C7113.5 (2)C10—C9—H9B109.6
C11—C10—C9111.9 (3)C8—C9—H9B109.6
C11—C10—H10A109.2H9A—C9—H9B108.1
C9—C10—H10A109.2C15—C16—C17120.3 (3)
C11—C10—H10B109.2C15—C16—H16119.9
C9—C10—H10B109.2C17—C16—H16119.9
H10A—C10—H10B107.9C23—C22—C21120.0 (3)
C23—C18—C19119.7 (3)C23—C22—H22120.0
C23—C18—C11119.6 (3)C21—C22—H22120.0
C19—C18—C11120.6 (3)C13—C14—C15120.4 (3)
C2—C1—C6119.7 (3)C13—C14—H14119.8
C2—C1—P1119.6 (2)C15—C14—H14119.8
C6—C1—P1120.7 (2)C20—C19—C18119.6 (3)
C13—C12—C17119.1 (3)C20—C19—H19120.2
C13—C12—C7121.7 (3)C18—C19—H19120.2
C17—C12—C7119.2 (3)C4—C3—C2120.4 (3)
O1—C11—C10111.8 (3)C4—C3—H3119.8
O1—C11—C18108.3 (2)C2—C3—H3119.8
C10—C11—C18113.8 (3)C18—C23—C22120.3 (3)
O1—C11—Se2105.63 (19)C18—C23—H23119.9
C10—C11—Se2109.0 (2)C22—C23—H23119.9
C18—C11—Se2107.8 (2)O1—C7—C8110.9 (3)
C7—C8—C9113.0 (3)O1—C7—C12107.9 (2)
C7—C8—H8A109.0C8—C7—C12112.2 (3)
C9—C8—H8A109.0O1—C7—P1104.0 (2)
C7—C8—H8B109.0C8—C7—P1112.1 (2)
C9—C8—H8B109.0C12—C7—P1109.4 (2)
H8A—C8—H8B107.8C14—C13—C12120.2 (3)
C5—C6—C1120.0 (3)C14—C13—H13119.9
C5—C6—H6120.0C12—C13—H13119.9
C1—C6—H6120.0C16—C15—C14119.7 (3)
C16—C17—C12120.3 (3)C16—C15—H15120.1
C16—C17—H17119.8C14—C15—H15120.1
C12—C17—H17119.8C21—C20—C19121.0 (3)
C3—C4—C5120.3 (3)C21—C20—H20119.5
C3—C4—H4119.9C19—C20—H20119.5
C11—Se2—P1—C1104.65 (14)C23—C18—C19—C20−0.2 (5)
C11—Se2—P1—C7−4.46 (13)C11—C18—C19—C20177.3 (3)
C11—Se2—P1—Se1−126.97 (10)C5—C4—C3—C2−0.4 (6)
C3—C2—C1—C61.6 (5)C1—C2—C3—C4−0.8 (5)
C3—C2—C1—P1−176.7 (3)C19—C18—C23—C22−0.7 (5)
C7—P1—C1—C2−117.1 (3)C11—C18—C23—C22−178.2 (3)
Se1—P1—C1—C210.6 (3)C21—C22—C23—C180.5 (5)
Se2—P1—C1—C2141.8 (3)C11—O1—C7—C857.7 (3)
C7—P1—C1—C664.7 (3)C11—O1—C7—C12−179.0 (3)
Se1—P1—C1—C6−167.6 (2)C11—O1—C7—P1−63.0 (3)
Se2—P1—C1—C6−36.4 (3)C9—C8—C7—O1−52.0 (3)
C7—O1—C11—C10−59.4 (3)C9—C8—C7—C12−172.7 (2)
C7—O1—C11—C18174.3 (3)C9—C8—C7—P163.7 (3)
C7—O1—C11—Se259.0 (3)C13—C12—C7—O13.9 (4)
C9—C10—C11—O154.2 (3)C17—C12—C7—O1−173.9 (3)
C9—C10—C11—C18177.4 (3)C13—C12—C7—C8126.3 (3)
C9—C10—C11—Se2−62.2 (3)C17—C12—C7—C8−51.5 (4)
C23—C18—C11—O1−172.4 (3)C13—C12—C7—P1−108.6 (3)
C19—C18—C11—O110.1 (4)C17—C12—C7—P173.6 (3)
C23—C18—C11—C1062.5 (4)C1—P1—C7—O1−74.6 (2)
C19—C18—C11—C10−115.0 (3)Se1—P1—C7—O1158.24 (15)
C23—C18—C11—Se2−58.5 (4)Se2—P1—C7—O133.03 (19)
C19—C18—C11—Se2124.0 (3)C1—P1—C7—C8165.6 (2)
P1—Se2—C11—O1−24.59 (19)Se1—P1—C7—C838.4 (3)
P1—Se2—C11—C1095.7 (2)Se2—P1—C7—C8−86.8 (2)
P1—Se2—C11—C18−140.2 (2)C1—P1—C7—C1240.4 (3)
C2—C1—C6—C5−1.2 (5)Se1—P1—C7—C12−86.7 (2)
P1—C1—C6—C5177.0 (3)Se2—P1—C7—C12148.1 (2)
C13—C12—C17—C16−0.1 (5)C15—C14—C13—C12−0.6 (5)
C7—C12—C17—C16177.8 (3)C17—C12—C13—C140.6 (5)
C1—C6—C5—C40.0 (5)C7—C12—C13—C14−177.2 (3)
C3—C4—C5—C60.8 (6)C17—C16—C15—C140.4 (5)
C11—C10—C9—C8−48.4 (4)C13—C14—C15—C160.2 (6)
C7—C8—C9—C1047.9 (4)C22—C21—C20—C19−1.4 (5)
C12—C17—C16—C15−0.4 (5)C18—C19—C20—C211.3 (6)
C20—C21—C22—C230.5 (5)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: PV2051).

References

  • An, D. L., Higeta, N., Toyota, K. & Yoshifuji, M. (1998). Chem. Lett. pp. 17–18.
  • Bhattacharyya, P., Slawin, A. M. Z. & Woollins, J. D. (2000). Angew. Chem. Int. Ed. Engl.39, 1973–1974. [PubMed]
  • Bhattacharyya, P., Slawin, A. M. Z. & Woollins, J. D. (2001a). Dalton Trans. 300–303.
  • Bhattacharyya, P., Slawin, A. M. Z. & Woollins, J. D. (2001b). J. Organomet. Chem.623, 116–119.
  • Bhattacharyya, P., Slawin, A. M. Z. & Woollins, J. D. (2002). Chem. Eur. J.8, 2705–2711. [PubMed]
  • Fitzmaurice, J. C., Williams, D. J., Wood, P. T. & Woollins, J. D. (1988). J. Chem. Soc. Chem. Commun. pp. 741–743.
  • Gray, I. P., Bhattacharyya, P., Slawin, A. M. Z. & Woollins, J. D. (2005). Chem. Eur. J.11, 6221–6227. [PubMed]
  • Gray, I. P., Slawin, A. M. Z. & Woollins, J. D. (2005). Dalton Trans. pp. 2188–2194. [PubMed]
  • Hua, G., Li, Y., Slawin, A. M. Z. & Woollins, J. D. (2006). Org. Lett.8, 5251–5254. [PubMed]
  • Hua, G., Li, Y., Slawin, A. M. Z. & Woollins, J. D. (2007a). Eur. J. Inorg. Chem. pp. 891–897.
  • Hua, G., Li, Y., Slawin, A. M. Z. & Woollins, J. D. (2007b). Chem. Commun. pp. 1465–1467. [PubMed]
  • Hua, G., Li, Y., Slawin, A. M. Z. & Woollins, J. D. (2007c). Dalton Trans. pp. 1477–1480. [PubMed]
  • Hua, G. & Woollins, J. D. (2007). Tetrahedron Lett.48, 3677–3679.
  • Rigaku (2004). CrystalClear Version 1.36. Rigaku Corporation, Tokyo, Japan.
  • Sheldrick, G. M. (1997). SHELXS97 and SHELXL97 University of Göttingen, Germany.
  • Sheldrick, G. M. (2003). SHELXTL Version 6.14. Bruker AXS Inc., Madison, Wisconsin, USA.
  • Shi, W., Fallah, M. S., Anson, C. E. & Rothenberger, A. (2006). Dalton Trans. pp. 2979–2983. [PubMed]
  • Shi, W., Fallah, M. S., Zhang, L., Anson, C. E., Matern, E. & Rothenberger, A. (2007). Chem. Eur. J.13, 598–603. [PubMed]

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