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Acta Cryst. (2008). E64, m1120    [ doi:10.1107/S1600536808024343 ]

Low-temperature redetermination of aquachloridotriphenyltin(IV)-1,10-phenanthroline (1/1)

S. W. Ng

Abstract top

The crystal structure of the title compound, [Sn(C6H5)3Cl(H2O)]·C12H8N2, which was refined in the triclinic space group P\overline{1} [Fu, Gao, Ma & Zhang (2005). Chin. J. Synth. Chem. 13, 55-57], has been redetermined in the monoclinic space group C2/c from low-temperature diffraction measurements. The Sn atom is five-coordinate in a trans-C3SnClO trigonal-bipyramidal geometry; the coordinated water molecule forms a pair of hydrogen bonds to the nitrogen heterocycle.

Comment top

Interest in aquachlorotriphenyltin.1,10-phenanthroline (Scheme I) involves the existence of a monoclinic P21/c modification [11.960 (1), 12.220 (1), 17.854 (1) Å, β 92.41 (1) °] (Ng & Kumar Das, 1996) that is, in fact, commensurately modulated in P21/n [21.1053 (5), 12.2347 (3), 51.772 (2) Å,101.525 (2) °] (Rae et al., 2005). The compound has the coordinated water molecules of two aquachlorotriphenyltin entities each forming hydrogen bonds to two N-heterocycles. A reported triclinic modification (Fu et al., 2005) has an unit cell [P1: 12.064 (4), 12.075 (4), 18.603 (6) Å, 89.562 (6), 99.567 (5), 72.702 (5) °; V 2672 (5) Å3] that readily transforms to a monoclinic C2/c unit cell. In the correct symmetry, the tin atom is five-coordinate in a trans-C3SnClO trigonal bipyramidal geometry; the coordinated water molecule forms a pair of hydrogen bonds to one N-heterocycle only (Fig. 1, Table 1).

Related literature top

For a description of the title compound in the triclinic space group P1, see: Fu et al. (2005). Aquachlorotri(p-chlorophenyl)tin.1,10-phenanthroline exists as a hydrogen-bonded dinuclear compound, see: Ng & Kumar Das (1996). This study also mentions the existence of a monoclinic P21/c modification of the title compound. This modification is, in fact, commensurately modulated; see: Rae et al. (2005).

Experimental top

Triphenyltin chloride (0.39 g, 1 mmol) and 1,10-phenanthroline monohydrate (0.20 g, 1 mmol) were dissolved in hot ethanol (10 ml). Crystals of the compound separated after a day.

Refinement top

The carbon-bound hydrogen atoms were placed at calculated positions with C—H = 0.95 Å, and with U(H) = 1.2Ueq(C). The water H-atoms were refined with a distance restraint of O—H 0.84±0.01 Å.

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2008).

Figures top
[Figure 1] Fig. 1. Thermal ellipsoid plot (Barbour, 2001) plot of monoclinic SnCl(H2O)(C6H5)3.C12H8N2 at the 70% probability level. Hydrogen atoms are drawn as spheres of arbitrary radius. Hydrogen bonds are shown as dashed lines.
aquachloridotriphenyltin(IV)–1,10-phenanthroline (1/1) top
Crystal data top
[Sn(C6H5)3Cl(H2O)]·C12H8N2F000 = 2352
Mr = 583.66Dx = 1.541 Mg m−3
Monoclinic, C2/cMo Kα radiation
λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 9047 reflections
a = 16.3739 (2) Åθ = 2.3–28.3º
b = 17.3120 (2) ŵ = 1.15 mm−1
c = 18.4295 (2) ÅT = 100 (2) K
β = 105.602 (1)ºBlock, colorless
V = 5031.6 (1) Å30.30 × 0.20 × 0.10 mm
Z = 8
Data collection top
Bruker SMART APEX
diffractometer		5333 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.015
Monochromator: graphiteθmax = 27.5º
ω scansθmin = 1.8º
Absorption correction: Multi-scan
(SADABS; Sheldrick, 1996)		h = −21→21
Tmin = 0.768, Tmax = 0.894k = −22→22
23117 measured reflectionsl = −22→23
5746 independent reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.020H atoms treated by a mixture of
independent and constrained refinement
wR(F2) = 0.052  w = 1/[σ2(Fo2) + (0.0231P)2 + 10.9613P]
where P = (Fo2 + 2Fc2)/3
S = 1.01(Δ/σ)max = 0.001
5746 reflectionsΔρmax = 0.72 e Å−3
324 parametersΔρmin = −0.60 e Å−3
2 restraintsExtinction correction: none
Primary atom site location: structure-invariant direct methods
Crystal data top
[Sn(C6H5)3Cl(H2O)]·C12H8N2V = 5031.6 (1) Å3
Mr = 583.66Z = 8
Monoclinic, C2/cMo Kα
a = 16.3739 (2) ŵ = 1.15 mm−1
b = 17.3120 (2) ÅT = 100 (2) K
c = 18.4295 (2) Å0.30 × 0.20 × 0.10 mm
β = 105.602 (1)º
Data collection top
Bruker SMART APEX
diffractometer		5746 independent reflections
Absorption correction: Multi-scan
(SADABS; Sheldrick, 1996)		5333 reflections with I > 2σ(I)
Tmin = 0.768, Tmax = 0.894Rint = 0.015
23117 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0202 restraints
wR(F2) = 0.052H atoms treated by a mixture of
independent and constrained refinement
S = 1.01  w = 1/[σ2(Fo2) + (0.0231P)2 + 10.9613P]
where P = (Fo2 + 2Fc2)/3
5746 reflectionsΔρmax = 0.72 e Å−3
324 parametersΔρmin = −0.60 e Å−3
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Sn10.283489 (7)0.505787 (6)0.562615 (6)0.01482 (4)
Cl10.18859 (3)0.44885 (2)0.44433 (2)0.02027 (8)
O10.37284 (8)0.56254 (7)0.67064 (7)0.0195 (2)
H1O0.3578 (17)0.6082 (8)0.6762 (16)0.050 (8)*
H2O0.4223 (9)0.5695 (16)0.6674 (16)0.053 (8)*
N10.36099 (9)0.71863 (8)0.67875 (8)0.0188 (3)
N20.50883 (9)0.65084 (9)0.65883 (8)0.0216 (3)
C10.34419 (10)0.58146 (9)0.50254 (9)0.0172 (3)
C20.40237 (12)0.55391 (11)0.46606 (11)0.0264 (4)
H20.41150.49990.46360.032*
C30.44752 (13)0.60528 (14)0.43296 (12)0.0343 (5)
H30.48720.58610.40810.041*
C40.43462 (13)0.68404 (13)0.43620 (12)0.0330 (5)
H40.46620.71890.41460.040*
C50.37588 (13)0.71172 (11)0.47086 (11)0.0287 (4)
H50.36620.76570.47230.034*
C60.33064 (12)0.66094 (10)0.50385 (10)0.0214 (3)
H60.29010.68060.52750.026*
C70.33380 (10)0.39676 (9)0.60801 (10)0.0179 (3)
C80.36605 (13)0.38717 (11)0.68536 (11)0.0274 (4)
H80.37160.43060.71780.033*
C90.39024 (15)0.31425 (13)0.71554 (13)0.0366 (5)
H90.41200.30820.76850.044*
C100.38270 (13)0.25093 (11)0.66890 (13)0.0331 (5)
H100.39820.20120.68980.040*
C110.35274 (12)0.25958 (10)0.59211 (13)0.0292 (4)
H110.34930.21610.56000.035*
C120.32755 (11)0.33198 (10)0.56158 (11)0.0218 (3)
H120.30590.33750.50860.026*
C130.18329 (10)0.54725 (9)0.60574 (10)0.0178 (3)
C140.19228 (12)0.54833 (10)0.68337 (10)0.0217 (3)
H140.24440.53270.71710.026*
C150.12560 (13)0.57213 (10)0.71168 (11)0.0264 (4)
H150.13210.57240.76450.032*
C160.04974 (13)0.59533 (11)0.66251 (12)0.0292 (4)
H160.00430.61170.68180.035*
C170.03984 (12)0.59478 (11)0.58568 (12)0.0281 (4)
H17−0.01220.61100.55220.034*
C180.10621 (11)0.57037 (10)0.55742 (11)0.0222 (3)
H180.09890.56940.50450.027*
C190.29276 (11)0.75240 (11)0.68954 (10)0.0226 (4)
H190.24980.72040.69940.027*
C200.27997 (12)0.83268 (11)0.68733 (11)0.0273 (4)
H200.23010.85430.69590.033*
C210.34104 (13)0.87859 (11)0.67250 (11)0.0282 (4)
H210.33400.93310.67040.034*
C220.41470 (12)0.84523 (10)0.66025 (10)0.0234 (4)
C230.42300 (11)0.76392 (10)0.66440 (9)0.0184 (3)
C240.47983 (13)0.89168 (11)0.64384 (11)0.0300 (4)
H240.47370.94630.64130.036*
C250.54943 (13)0.85914 (12)0.63203 (11)0.0309 (4)
H250.59150.89100.62060.037*
C260.56146 (12)0.77707 (12)0.63629 (10)0.0257 (4)
C270.49893 (11)0.72867 (10)0.65276 (9)0.0201 (3)
C280.63516 (12)0.74201 (14)0.62609 (11)0.0326 (5)
H280.67810.77270.61450.039*
C290.64472 (13)0.66405 (14)0.63288 (11)0.0346 (5)
H290.69420.63950.62650.042*
C300.57960 (12)0.62074 (12)0.64960 (11)0.0283 (4)
H300.58680.56640.65460.034*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Sn10.01639 (6)0.01177 (6)0.01746 (6)−0.00055 (4)0.00652 (4)−0.00002 (4)
Cl10.02075 (19)0.01617 (18)0.0221 (2)−0.00109 (14)0.00273 (15)−0.00226 (14)
O10.0198 (6)0.0156 (6)0.0235 (6)−0.0023 (5)0.0066 (5)−0.0015 (5)
N10.0187 (7)0.0197 (7)0.0170 (7)−0.0021 (5)0.0033 (6)−0.0004 (5)
N20.0213 (7)0.0260 (7)0.0176 (7)0.0007 (6)0.0051 (6)−0.0019 (6)
C10.0168 (8)0.0183 (8)0.0160 (8)−0.0034 (6)0.0033 (6)0.0001 (6)
C20.0241 (9)0.0281 (9)0.0296 (10)0.0026 (7)0.0118 (8)0.0030 (7)
C30.0222 (9)0.0508 (13)0.0341 (11)−0.0009 (9)0.0152 (8)0.0082 (9)
C40.0270 (10)0.0426 (11)0.0272 (10)−0.0153 (9)0.0035 (8)0.0114 (9)
C50.0363 (11)0.0216 (9)0.0234 (9)−0.0116 (8)−0.0002 (8)0.0035 (7)
C60.0264 (9)0.0188 (8)0.0183 (8)−0.0031 (7)0.0046 (7)−0.0003 (6)
C70.0151 (7)0.0169 (7)0.0240 (9)0.0004 (6)0.0091 (6)0.0027 (6)
C80.0338 (10)0.0258 (9)0.0240 (9)0.0089 (8)0.0102 (8)0.0037 (7)
C90.0460 (13)0.0365 (11)0.0307 (11)0.0169 (10)0.0161 (10)0.0148 (9)
C100.0320 (10)0.0213 (9)0.0506 (13)0.0112 (8)0.0190 (10)0.0157 (9)
C110.0227 (9)0.0150 (8)0.0517 (13)0.0007 (7)0.0132 (9)−0.0005 (8)
C120.0180 (8)0.0179 (8)0.0300 (9)−0.0011 (6)0.0074 (7)−0.0003 (7)
C130.0191 (8)0.0112 (7)0.0254 (9)−0.0023 (6)0.0102 (7)−0.0011 (6)
C140.0243 (9)0.0168 (8)0.0260 (9)−0.0002 (7)0.0102 (7)−0.0006 (6)
C150.0363 (10)0.0198 (8)0.0288 (10)−0.0002 (7)0.0189 (8)−0.0015 (7)
C160.0291 (10)0.0226 (9)0.0439 (12)0.0031 (7)0.0235 (9)0.0005 (8)
C170.0209 (9)0.0248 (9)0.0403 (11)0.0038 (7)0.0114 (8)0.0035 (8)
C180.0232 (9)0.0188 (8)0.0264 (9)0.0005 (6)0.0095 (7)0.0018 (7)
C190.0197 (8)0.0270 (9)0.0196 (9)0.0000 (7)0.0028 (7)−0.0005 (7)
C200.0246 (9)0.0276 (9)0.0267 (10)0.0069 (7)0.0019 (8)−0.0024 (7)
C210.0341 (10)0.0200 (8)0.0242 (9)0.0044 (7)−0.0030 (8)−0.0001 (7)
C220.0275 (9)0.0213 (8)0.0168 (8)−0.0039 (7)−0.0018 (7)0.0010 (6)
C230.0205 (8)0.0196 (8)0.0126 (7)−0.0029 (6)0.0002 (6)0.0000 (6)
C240.0372 (11)0.0223 (9)0.0245 (10)−0.0112 (8)−0.0018 (8)0.0049 (7)
C250.0312 (10)0.0364 (11)0.0219 (9)−0.0183 (8)0.0015 (8)0.0057 (8)
C260.0227 (9)0.0377 (10)0.0154 (8)−0.0088 (8)0.0032 (7)0.0010 (7)
C270.0200 (8)0.0261 (8)0.0134 (8)−0.0048 (7)0.0027 (6)−0.0005 (6)
C280.0231 (9)0.0547 (13)0.0214 (9)−0.0102 (9)0.0082 (8)−0.0015 (9)
C290.0236 (9)0.0586 (14)0.0239 (10)0.0023 (9)0.0104 (8)−0.0066 (9)
C300.0279 (10)0.0360 (10)0.0211 (9)0.0032 (8)0.0068 (8)−0.0055 (8)
Geometric parameters (Å, °) top
Sn1—C12.127 (2)C12—H120.9500
Sn1—C72.138 (2)C13—C181.393 (2)
Sn1—C132.131 (2)C13—C141.398 (2)
Sn1—O12.346 (1)C14—C151.393 (2)
Sn1—Cl12.5132 (4)C14—H140.9500
O1—H1O0.84 (1)C15—C161.386 (3)
O1—H2O0.84 (1)C15—H150.9500
N1—C191.322 (2)C16—C171.381 (3)
N1—C231.364 (2)C16—H160.9500
N2—C301.323 (2)C17—C181.391 (2)
N2—C271.358 (2)C17—H170.9500
C1—C61.395 (2)C18—H180.9500
C1—C21.390 (2)C19—C201.405 (3)
C2—C31.397 (3)C19—H190.9500
C2—H20.9500C20—C211.361 (3)
C3—C41.384 (3)C20—H200.9500
C3—H30.9500C21—C221.409 (3)
C4—C51.376 (3)C21—H210.9500
C4—H40.9500C22—C231.414 (2)
C5—C61.390 (2)C22—C241.432 (3)
C5—H50.9500C23—C271.452 (2)
C6—H60.9500C24—C251.340 (3)
C7—C121.398 (2)C24—H240.9500
C7—C81.391 (3)C25—C261.434 (3)
C8—C91.393 (3)C25—H250.9500
C8—H80.9500C26—C281.408 (3)
C9—C101.378 (3)C26—C271.418 (2)
C9—H90.9500C28—C291.361 (3)
C10—C111.376 (3)C28—H280.9500
C10—H100.9500C29—C301.404 (3)
C11—C121.390 (2)C29—H290.9500
C11—H110.9500C30—H300.9500
C1—Sn1—C7124.25 (6)C14—C13—Sn1120.42 (13)
C1—Sn1—C13120.08 (6)C13—C14—C15120.64 (18)
C1—Sn1—O184.93 (5)C13—C14—H14119.7
C1—Sn1—Cl193.24 (5)C15—C14—H14119.7
C7—Sn1—C13113.94 (6)C16—C15—C14119.73 (18)
C7—Sn1—Cl194.38 (5)C16—C15—H15120.1
C7—Sn1—O187.19 (6)C14—C15—H15120.1
C13—Sn1—O184.80 (6)C15—C16—C17120.38 (17)
C13—Sn1—Cl195.58 (5)C15—C16—H16119.8
O1—Sn1—Cl1178.06 (3)C17—C16—H16119.8
Sn1—O1—H1o111.1 (19)C16—C17—C18119.86 (18)
Sn1—O1—H2o113 (2)C16—C17—H17120.1
H1o—O1—H2o101 (3)C18—C17—H17120.1
C19—N1—C23118.57 (15)C17—C18—C13120.82 (18)
C30—N2—C27118.00 (16)C17—C18—H18119.6
C6—C1—C2118.67 (16)C13—C18—H18119.6
C6—C1—Sn1119.99 (12)N1—C19—C20123.95 (17)
C2—C1—Sn1121.17 (13)N1—C19—H19118.0
C1—C2—C3120.32 (18)C20—C19—H19118.0
C1—C2—H2119.8C21—C20—C19118.14 (17)
C3—C2—H2119.8C21—C20—H20120.9
C4—C3—C2120.23 (19)C19—C20—H20120.9
C4—C3—H3119.9C20—C21—C22119.97 (17)
C2—C3—H3119.9C20—C21—H21120.0
C5—C4—C3119.82 (17)C22—C21—H21120.0
C5—C4—H4120.1C23—C22—C21118.24 (17)
C3—C4—H4120.1C23—C22—C24120.29 (18)
C4—C5—C6120.27 (18)C21—C22—C24121.47 (17)
C4—C5—H5119.9N1—C23—C22121.12 (16)
C6—C5—H5119.9N1—C23—C27119.92 (15)
C5—C6—C1120.67 (17)C22—C23—C27118.95 (16)
C5—C6—H6119.7C25—C24—C22120.82 (18)
C1—C6—H6119.7C25—C24—H24119.6
C12—C7—C8118.48 (16)C22—C24—H24119.6
C12—C7—Sn1120.79 (13)C24—C25—C26121.20 (17)
C8—C7—Sn1120.45 (13)C24—C25—H25119.4
C9—C8—C7120.42 (19)C26—C25—H25119.4
C9—C8—H8119.8C28—C26—C27117.91 (18)
C7—C8—H8119.8C28—C26—C25122.01 (18)
C10—C9—C8120.2 (2)C27—C26—C25120.06 (18)
C10—C9—H9119.9N2—C27—C26121.80 (17)
C8—C9—H9119.9N2—C27—C23119.53 (15)
C11—C10—C9120.17 (18)C26—C27—C23118.66 (16)
C11—C10—H10119.9C29—C28—C26119.80 (18)
C9—C10—H10119.9C29—C28—H28120.1
C10—C11—C12119.95 (18)C26—C28—H28120.1
C10—C11—H11120.0C28—C29—C30118.33 (19)
C12—C11—H11120.0C28—C29—H29120.8
C11—C12—C7120.72 (18)C30—C29—H29120.8
C11—C12—H12119.6N2—C30—C29124.1 (2)
C7—C12—H12119.6N2—C30—H30117.9
C18—C13—C14118.56 (16)C29—C30—H30117.9
C18—C13—Sn1120.95 (13)
C13—Sn1—C1—C612.62 (16)C18—C13—C14—C15−0.1 (2)
C7—Sn1—C1—C6−151.49 (13)Sn1—C13—C14—C15−177.11 (13)
O1—Sn1—C1—C6−68.37 (14)C13—C14—C15—C16−0.3 (3)
Cl1—Sn1—C1—C6110.98 (13)C14—C15—C16—C170.2 (3)
C13—Sn1—C1—C2−172.10 (14)C15—C16—C17—C180.4 (3)
C7—Sn1—C1—C223.79 (17)C16—C17—C18—C13−0.8 (3)
O1—Sn1—C1—C2106.90 (15)C14—C13—C18—C170.7 (3)
Cl1—Sn1—C1—C2−73.75 (14)Sn1—C13—C18—C17177.66 (13)
C6—C1—C2—C31.4 (3)C23—N1—C19—C20−0.2 (3)
Sn1—C1—C2—C3−173.93 (15)N1—C19—C20—C210.6 (3)
C1—C2—C3—C40.0 (3)C19—C20—C21—C22−0.3 (3)
C2—C3—C4—C5−1.3 (3)C20—C21—C22—C23−0.4 (3)
C3—C4—C5—C61.2 (3)C20—C21—C22—C24179.42 (18)
C4—C5—C6—C10.2 (3)C19—N1—C23—C22−0.6 (2)
C2—C1—C6—C5−1.5 (3)C19—N1—C23—C27179.62 (15)
Sn1—C1—C6—C5173.91 (13)C21—C22—C23—N10.9 (3)
C1—Sn1—C7—C12−78.22 (15)C24—C22—C23—N1−178.92 (16)
C13—Sn1—C7—C12116.81 (13)C21—C22—C23—C27−179.32 (16)
O1—Sn1—C7—C12−160.15 (13)C24—C22—C23—C270.8 (3)
Cl1—Sn1—C7—C1218.72 (13)C23—C22—C24—C250.1 (3)
C1—Sn1—C7—C8108.01 (14)C21—C22—C24—C25−179.75 (18)
C13—Sn1—C7—C8−56.97 (16)C22—C24—C25—C26−0.7 (3)
O1—Sn1—C7—C826.08 (14)C24—C25—C26—C28−178.24 (19)
Cl1—Sn1—C7—C8−155.05 (14)C24—C25—C26—C270.4 (3)
C12—C7—C8—C9−1.0 (3)C30—N2—C27—C260.6 (3)
Sn1—C7—C8—C9172.95 (15)C30—N2—C27—C23−178.48 (16)
C7—C8—C9—C100.2 (3)C28—C26—C27—N20.1 (3)
C8—C9—C10—C111.2 (3)C25—C26—C27—N2−178.60 (17)
C9—C10—C11—C12−2.0 (3)C28—C26—C27—C23179.23 (16)
C10—C11—C12—C71.2 (3)C25—C26—C27—C230.5 (3)
C8—C7—C12—C110.2 (3)N1—C23—C27—N2−2.2 (2)
Sn1—C7—C12—C11−173.66 (13)C22—C23—C27—N2178.03 (16)
C1—Sn1—C13—C1866.35 (15)N1—C23—C27—C26178.62 (16)
C7—Sn1—C13—C18−127.99 (13)C22—C23—C27—C26−1.1 (2)
O1—Sn1—C13—C18147.42 (13)C27—C26—C28—C29−0.6 (3)
Cl1—Sn1—C13—C18−30.67 (13)C25—C26—C28—C29178.06 (19)
C1—Sn1—C13—C14−116.71 (13)C26—C28—C29—C300.4 (3)
C7—Sn1—C13—C1448.95 (15)C27—N2—C30—C29−0.9 (3)
O1—Sn1—C13—C14−35.64 (13)C28—C29—C30—N20.4 (3)
Cl1—Sn1—C13—C14146.27 (12)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O1—H1o···N10.84 (1)1.91 (1)2.716 (2)159 (3)
O1—H2o···N20.84 (1)2.03 (2)2.757 (2)144 (3)
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O1—H1o···N10.84 (1)1.91 (1)2.716 (2)159 (3)
O1—H2o···N20.84 (1)2.03 (2)2.757 (2)144 (3)
Acknowledgements top

The University of Malaya is thanked for supporting this study through the purchase of the diffractometer.

references
References top

Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191.

Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.

Fu, C.-X., Gao, Z.-H., Ma, C.-L. & Zhang, J.-H. (2005). Chin. J. Synth. Chem. 13, 55–57.

Ng, S. W. & Kumar Das, V. G. (1996). J. Organomet. Chem. 513, 105–108.

Rae, A. D., Haller, K. J. & Ng, S. W. (2005). J. S. T. Tropics, 1, 157–163.

Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.

Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.

Westrip, S. P. (2008). publCIF. In preparation.