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metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 67| Part 2| February 2011| Page m148
doi:10.1107/S1600536810054061

Bis(μ-3,5-di­fluorobenzoato)bis­[(3,5-di­fluorobenzoato)di­methyltin(IV)]

Hong Liu,a Han-Dong Yin,a* Jing Lia and Da-Qi Wanga

aCollege of Chemistry and Chemical Engineering, Liaocheng University, Shandong 252059, People's Republic of China
*Correspondence e-mail: handongyin@163.com

(Received 24 November 2010; accepted 24 December 2010; online 8 January 2011)

In the dinuclear title complex, [Sn2(CH3)4(C7H3F2O2)4], the SnIV atom is chelated by two 3,5-difluoro­benzoate (dfb) anions and coordinated by two methyl groups while an O atom from the adjacent dfb anion bridges the Sb atom with a longer Sb—O bond distance of 2.793 (4) Å. The complex mol­ecule has 2 symmetry and the SnIV atom is in a distorted penta­gonal–bipyramidal coordination geometry. In the crystal, mol­ecules are connected by C—H⋯O and C—H⋯F hydrogen bonds.

Related literature

For applications of organotin compounds, see: Duboy & Roy (2003[Duboy, S. K. & Roy, U. (2003). Appl. Organomet. Chem. 17, 3-8.]). For related compounds, see: Yin et al. (2003[Yin, H.-D., Wang, C.-H., Wang, Y., Ma, C.-L. & Shao, J.-X. (2003). Chem. J. Chin. Univ. 24, 68-72.], 2005[Yin, H.-D., Hong, M., Wang, Q.-B., Xue, S.-C. & Wang, D.-Q. (2005). J. Organomet. Chem. 690, 1669-1676.]).

[Scheme 1]

Experimental

Crystal data

  • [Sn2(CH3)4(C7H3F2O2)4]

  • Mr = 925.90

  • Monoclinic, P 2/c

  • a = 16.4635 (15) Å

  • b = 7.5836 (8) Å

  • c = 15.1123 (14) Å

  • β = 115.680 (1)°

  • V = 1700.4 (3) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 1.56 mm−1

  • T = 298 K

  • 0.49 × 0.43 × 0.18 mm
Data collection

  • Bruker SMART CCD area detector diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.515, Tmax = 0.766

  • 8140 measured reflections

  • 2987 independent reflections

  • 2020 reflections with I > 2σ(I)

  • Rint = 0.059
Refinement

  • R[F2 > 2σ(F2)] = 0.043

  • wR(F2) = 0.127

  • S = 1.05

  • 2987 reflections

  • 228 parameters

  • H-atom parameters constrained

  • Δρmax = 1.47 e Å−3

  • Δρmin = −0.76 e Å−3

Table 1
Selected bond lengths (Å)

Sn1—O1 2.534 (4)
Sn1—O2 2.163 (4)
Sn1—O3 2.424 (4)
Sn1—O4 2.155 (4)
Sn1—C15 2.093 (6)
Sn1—C16 2.088 (6)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
C11—H11⋯F4i 0.93 2.49 3.326 (8) 149
C15—H15B⋯O4ii 0.96 2.52 3.474 (8) 171
Symmetry codes: (i) [-x-1, y, -z-{\script{1\over 2}}]; (ii) -x, -y+1, -z.

Data collection: SMART (Siemens, 1996[Siemens (1996). SMART and SAINT. Siemens Analytical X-ray Systems, Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Siemens, 1996[Siemens (1996). SMART and SAINT. Siemens Analytical X-ray Systems, Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810054061/xu5108sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810054061/xu5108Isup2.hkl

checkCIF report


Comment top

In recent years, organotin compounds have attracted increasing attention owing to their wide industrial applications and biological activities (Duboy & Roy, 2003). We have therefore synthesized the title compound, and present its crystal structure here. The molecular structure of the compound is shown Fig. 1. For this compound, the asymmetric unit contains twomonomers, which are different from a crystallographic point of view. In this compound we can found the Sn atom exists in a distorted pentagonal bipyramidal coordination environment. The atoms O1, O1A, O2, O3 and O4 are coplanar within 0.044 Å, which form the equatorial plane. Furthermore, the angle of the axial C16—Sn1—C15 is 156.8 (3)°, which deviates from the linear angle of 180. The O1 atom of the carboxylate residue also binds the other tin atom, Sn1A, generating a Sn2O2 four-membered ring. The distance of Sn—O1 [-x, y, 0.5 - z] (2.793 (4) Å) is relatively longer than that of Sn1—O1 (2.534 (4) Å), but is comparable to those found in related seven-coordinate diorganotin systems (Yin et al., 2003). Thereby, the molecular structure of this compound can be described as a dimer, and the coordination geometry of tin can also be described as a trans-C2SnO5 pentagonal bipyramid with the two methyl groups occupying axial positions (Yin et al., 2005).

The molecules are linked by C—H···O and C—H···F hydrogen bonds into a one-dimensional chain structure (Table 2).

Related literature top

For applications of organotin compounds, see: Duboy & Roy (2003). For related compounds, see: Yin et al. (2003, 2005).

Experimental top

3,5-Difluorobenzoic acid (0.4 mmol) was added to a methanol solution of sodium ethoxide (0.4 mmol) and heated at reflux for 0.5 h. To this solution was added dimethyltin dichloride (0.2 mmol) in benzene, and the mixture was refluxed for 5 h, cooled and filtered. The filtrate was evaporated in vacuo. The obtained solid was recrystallized from dichloromethane-petroleum ether. Anal. Calcd (%) for C16H12F4O4Sn (Mr = 462.95): C, 41.48; H, 2.60; Found (%): C, 41.49; H, 2.61.

Refinement top

The H atoms were positioned geometrically, with C—H = 0.96 (emthyl) and C—H = 0.93 Å (aromatic), and refined as riding on parent atoms with Uiso(H) = 1.5Ueq(C) for methyl and 1.2Ueq(C) for the others.

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT (Siemens, 1996); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of the compound, showing 50% probability displacement ellipsoids [symmetry code: (A) -x, y, -z + 1/2].
Bis(µ-3,5-difluorobenzoato)bis[(3,5-difluorobenzoato)dimethyltin(IV)] top
Crystal data top
[Sn2(C7H3F2O2)4(CH3)4]F(000) = 904
Mr = 925.90Dx = 1.808 Mg m−3
Monoclinic, P2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ycCell parameters from 2614 reflections
a = 16.4635 (15) Åθ = 2.7–26.6°
b = 7.5836 (8) ŵ = 1.56 mm−1
c = 15.1123 (14) ÅT = 298 K
β = 115.680 (1)°Block, colourless
V = 1700.4 (3) Å30.49 × 0.43 × 0.18 mm
Z = 2
Data collection top
Bruker SMART CCD area detector
diffractometer		2987 independent reflections
Radiation source: fine-focus sealed tube2020 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.059
ϕ and ω scansθmax = 25.0°, θmin = 2.7°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −19→18
Tmin = 0.515, Tmax = 0.766k = −8→9
8140 measured reflectionsl = −17→14
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.043Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.127H-atom parameters constrained
S = 1.05 w = 1/[σ2(Fo2) + (0.0583P)2 + 0.6314P]
where P = (Fo2 + 2Fc2)/3
2987 reflections(Δ/σ)max = 0.003
228 parametersΔρmax = 1.47 e Å−3
0 restraintsΔρmin = −0.76 e Å−3
Crystal data top
[Sn2(C7H3F2O2)4(CH3)4]V = 1700.4 (3) Å3
Mr = 925.90Z = 2
Monoclinic, P2/cMo Kα radiation
a = 16.4635 (15) ŵ = 1.56 mm−1
b = 7.5836 (8) ÅT = 298 K
c = 15.1123 (14) Å0.49 × 0.43 × 0.18 mm
β = 115.680 (1)°
Data collection top
Bruker SMART CCD area detector
diffractometer		2987 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		2020 reflections with I > 2σ(I)
Tmin = 0.515, Tmax = 0.766Rint = 0.059
8140 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0430 restraints
wR(F2) = 0.127H-atom parameters constrained
S = 1.05Δρmax = 1.47 e Å−3
2987 reflectionsΔρmin = −0.76 e Å−3
228 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Sn10.05503 (2)0.25943 (4)0.14161 (3)0.03506 (18)
O1−0.0907 (3)0.2541 (4)0.1601 (3)0.0409 (10)
O2−0.0783 (3)0.2418 (4)0.0214 (3)0.0435 (10)
O30.2139 (3)0.2807 (6)0.1809 (4)0.0566 (12)
C70.1896 (4)0.2814 (7)0.0903 (5)0.0436 (15)
C14−0.1268 (4)0.2370 (6)0.0687 (5)0.0355 (13)
C8−0.2252 (4)0.2015 (7)0.0135 (5)0.0394 (14)
C10.2555 (4)0.3085 (8)0.0476 (5)0.0464 (16)
O40.1056 (3)0.2649 (5)0.0319 (3)0.0456 (11)
C9−0.2776 (4)0.1879 (9)0.0649 (5)0.0507 (16)
H9−0.25280.20660.13240.061*
C60.2292 (4)0.2844 (8)−0.0504 (5)0.0499 (16)
H60.17040.2521−0.09170.060*
C13−0.2630 (4)0.1759 (10)−0.0862 (5)0.0580 (17)
H13−0.22860.1869−0.12110.070*
C160.0715 (4)−0.0095 (8)0.1744 (5)0.0531 (16)
H16A0.1342−0.03980.19910.080*
H16B0.0374−0.07630.11600.080*
H16C0.0507−0.03590.22320.080*
C20.3429 (4)0.3579 (9)0.1092 (5)0.0579 (18)
H20.36100.37440.17610.069*
C10−0.3662 (4)0.1465 (10)0.0133 (6)0.0649 (19)
C50.2920 (5)0.3092 (10)−0.0867 (6)0.066 (2)
C150.0618 (4)0.5303 (7)0.1706 (5)0.0487 (16)
H15A0.05960.54970.23230.073*
H15B0.01170.58850.11930.073*
H15C0.11710.57680.17360.073*
C11−0.4055 (5)0.1176 (11)−0.0845 (6)0.074 (2)
H11−0.46620.0879−0.11760.088*
C30.4014 (5)0.3813 (10)0.0687 (7)0.075 (2)
C40.3776 (5)0.3597 (10)−0.0286 (7)0.075 (2)
H40.41880.3790−0.05450.090*
C12−0.3522 (5)0.1341 (11)−0.1328 (5)0.072 (2)
F10.2678 (4)0.2848 (7)−0.1838 (4)0.1003 (17)
F3−0.4177 (3)0.1298 (8)0.0627 (4)0.1096 (18)
F4−0.3896 (3)0.1015 (9)−0.2298 (3)0.131 (2)
F20.4862 (3)0.4353 (7)0.1280 (4)0.1166 (19)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Sn10.0318 (3)0.0405 (3)0.0336 (3)−0.00191 (17)0.0148 (2)0.00056 (18)
O10.033 (2)0.057 (3)0.031 (2)−0.0018 (16)0.0131 (19)0.0003 (18)
O20.034 (2)0.055 (3)0.040 (3)−0.0061 (17)0.014 (2)−0.0040 (18)
O30.039 (3)0.084 (3)0.047 (3)0.001 (2)0.019 (2)0.004 (2)
C70.038 (4)0.044 (4)0.051 (4)−0.003 (3)0.022 (3)0.003 (3)
C140.034 (3)0.036 (3)0.036 (4)0.002 (2)0.014 (3)0.005 (3)
C80.033 (3)0.041 (3)0.040 (4)−0.001 (2)0.012 (3)0.000 (3)
C10.034 (3)0.049 (3)0.063 (5)−0.003 (3)0.027 (3)0.004 (3)
O40.033 (2)0.066 (3)0.038 (3)−0.0080 (18)0.016 (2)−0.0043 (19)
C90.042 (4)0.068 (4)0.040 (4)−0.001 (3)0.015 (3)−0.003 (3)
C60.040 (4)0.064 (4)0.045 (4)−0.003 (3)0.017 (3)0.001 (3)
C130.047 (4)0.079 (5)0.046 (4)−0.006 (4)0.018 (4)−0.001 (4)
C160.074 (4)0.036 (3)0.065 (4)0.006 (3)0.044 (4)0.004 (3)
C20.034 (3)0.077 (5)0.063 (5)−0.010 (3)0.021 (3)−0.005 (4)
C100.038 (4)0.097 (6)0.062 (5)−0.008 (4)0.023 (4)−0.002 (4)
C50.069 (5)0.077 (5)0.067 (6)0.005 (4)0.045 (5)0.004 (4)
C150.060 (4)0.037 (3)0.056 (4)−0.007 (3)0.032 (3)0.004 (3)
C110.034 (4)0.107 (7)0.068 (6)−0.017 (4)0.011 (4)−0.010 (5)
C30.045 (4)0.091 (6)0.091 (7)−0.013 (4)0.031 (5)−0.007 (5)
C40.060 (5)0.089 (6)0.095 (7)−0.008 (4)0.052 (5)0.010 (5)
C120.050 (4)0.102 (6)0.044 (5)−0.012 (4)0.001 (4)−0.009 (4)
F10.082 (3)0.166 (5)0.074 (4)0.000 (3)0.053 (3)−0.005 (3)
F30.049 (3)0.196 (6)0.092 (4)−0.018 (3)0.038 (3)−0.011 (4)
F40.066 (3)0.243 (7)0.054 (3)−0.034 (4)−0.003 (3)−0.030 (4)
F20.048 (3)0.183 (5)0.115 (4)−0.034 (3)0.031 (3)−0.013 (4)
Geometric parameters (Å, º) top
Sn1—O12.534 (4)C13—C121.364 (9)
Sn1—O1i2.793 (4)C13—H130.9300
Sn1—O22.163 (4)C16—H16A0.9600
Sn1—O32.424 (4)C16—H16B0.9600
Sn1—O42.155 (4)C16—H16C0.9600
Sn1—C152.093 (6)C2—C31.359 (9)
Sn1—C162.088 (6)C2—H20.9300
O1—C141.252 (7)C10—C111.350 (10)
O2—C141.283 (7)C10—F31.355 (7)
O3—C71.249 (8)C5—C41.353 (11)
C7—O41.284 (8)C5—F11.356 (9)
C7—C11.497 (8)C15—H15A0.9600
C14—C81.490 (8)C15—H15B0.9600
C8—C131.372 (9)C15—H15C0.9600
C8—C91.394 (8)C11—C121.369 (10)
C1—C61.363 (9)C11—H110.9300
C1—C21.385 (8)C3—F21.355 (8)
C9—C101.360 (8)C3—C41.357 (11)
C9—H90.9300C4—H40.9300
C6—C51.377 (9)C12—F41.344 (8)
C6—H60.9300
C16—Sn1—C15156.8 (3)C12—C13—C8118.3 (7)
C16—Sn1—O498.49 (19)C12—C13—H13120.8
C15—Sn1—O498.00 (18)C8—C13—H13120.8
C16—Sn1—O296.8 (2)Sn1—C16—H16A109.5
C15—Sn1—O2100.32 (19)Sn1—C16—H16B109.5
O4—Sn1—O286.84 (16)H16A—C16—H16B109.5
C16—Sn1—O389.49 (19)Sn1—C16—H16C109.5
C15—Sn1—O385.97 (18)H16A—C16—H16C109.5
O4—Sn1—O356.72 (16)H16B—C16—H16C109.5
O2—Sn1—O3143.56 (17)C3—C2—C1117.7 (7)
C16—Sn1—O189.44 (18)C3—C2—H2121.1
C15—Sn1—O187.67 (17)C1—C2—H2121.1
O4—Sn1—O1141.79 (15)C11—C10—F3118.0 (6)
O2—Sn1—O155.04 (15)C11—C10—C9123.5 (7)
O3—Sn1—O1161.28 (16)F3—C10—C9118.5 (7)
C14—O1—Sn184.2 (3)C4—C5—F1118.5 (7)
C14—O2—Sn1100.6 (4)C4—C5—C6122.0 (8)
C7—O3—Sn186.2 (4)F1—C5—C6119.5 (7)
O3—C7—O4119.4 (6)Sn1—C15—H15A109.5
O3—C7—C1121.8 (6)Sn1—C15—H15B109.5
O4—C7—C1118.8 (6)H15A—C15—H15B109.5
O1—C14—O2120.0 (5)Sn1—C15—H15C109.5
O1—C14—C8121.2 (5)H15A—C15—H15C109.5
O2—C14—C8118.8 (5)H15B—C15—H15C109.5
C13—C8—C9120.4 (6)C10—C11—C12117.1 (7)
C13—C8—C14120.4 (6)C10—C11—H11121.5
C9—C8—C14119.1 (6)C12—C11—H11121.5
C6—C1—C2121.0 (6)F2—C3—C4119.0 (7)
C6—C1—C7120.2 (6)F2—C3—C2118.0 (8)
C2—C1—C7118.9 (6)C4—C3—C2122.9 (7)
C7—O4—Sn197.6 (4)C5—C4—C3118.0 (7)
C10—C9—C8117.9 (6)C5—C4—H4121.0
C10—C9—H9121.1C3—C4—H4121.0
C8—C9—H9121.1F4—C12—C13119.2 (7)
C1—C6—C5118.4 (7)F4—C12—C11118.0 (7)
C1—C6—H6120.8C13—C12—C11122.8 (7)
C5—C6—H6120.8
C16—Sn1—O1—C14−96.4 (3)C1—C7—O4—Sn1−174.4 (4)
C15—Sn1—O1—C14106.7 (3)C16—Sn1—O4—C7−85.4 (4)
O4—Sn1—O1—C146.7 (4)C15—Sn1—O4—C778.2 (3)
O2—Sn1—O1—C142.4 (3)O2—Sn1—O4—C7178.1 (3)
O3—Sn1—O1—C14176.9 (4)O3—Sn1—O4—C7−1.6 (3)
C16—Sn1—O2—C1482.1 (3)O1—Sn1—O4—C7174.6 (3)
C15—Sn1—O2—C14−82.1 (3)C13—C8—C9—C100.9 (10)
O4—Sn1—O2—C14−179.7 (3)C14—C8—C9—C10−176.7 (6)
O3—Sn1—O2—C14−179.4 (3)C2—C1—C6—C50.5 (10)
O1—Sn1—O2—C14−2.4 (3)C7—C1—C6—C5−179.4 (6)
C16—Sn1—O3—C7102.2 (4)C9—C8—C13—C12−1.1 (10)
C15—Sn1—O3—C7−100.6 (4)C14—C8—C13—C12176.4 (6)
O4—Sn1—O3—C71.7 (3)C6—C1—C2—C30.0 (10)
O2—Sn1—O3—C71.3 (5)C7—C1—C2—C3179.9 (6)
O1—Sn1—O3—C7−171.1 (4)C8—C9—C10—C110.2 (12)
Sn1—O3—C7—O4−2.7 (5)C8—C9—C10—F3178.8 (6)
Sn1—O3—C7—C1174.7 (5)C1—C6—C5—C4−1.4 (11)
Sn1—O1—C14—O2−3.8 (4)C1—C6—C5—F1179.5 (6)
Sn1—O1—C14—C8173.0 (4)F3—C10—C11—C12−179.6 (7)
Sn1—O2—C14—O14.5 (5)C9—C10—C11—C12−0.9 (13)
Sn1—O2—C14—C8−172.3 (4)C1—C2—C3—F2177.8 (6)
O1—C14—C8—C13−177.3 (6)C1—C2—C3—C40.5 (12)
O2—C14—C8—C13−0.5 (8)F1—C5—C4—C3−179.1 (7)
O1—C14—C8—C90.2 (8)C6—C5—C4—C31.8 (12)
O2—C14—C8—C9177.0 (5)F2—C3—C4—C5−178.7 (7)
O3—C7—C1—C6170.9 (6)C2—C3—C4—C5−1.3 (13)
O4—C7—C1—C6−11.6 (8)C8—C13—C12—F4−177.3 (7)
O3—C7—C1—C2−9.0 (9)C8—C13—C12—C110.4 (12)
O4—C7—C1—C2168.4 (5)C10—C11—C12—F4178.3 (8)
O3—C7—O4—Sn13.1 (6)C10—C11—C12—C130.6 (13)
Symmetry code: (i) −x, y, −z+1/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C11—H11···F4ii0.932.493.326 (8)149
C15—H15B···O4iii0.962.523.474 (8)171
Symmetry codes: (ii) −x−1, y, −z−1/2; (iii) −x, −y+1, −z.

Experimental details

Crystal data
Chemical formula[Sn2(C7H3F2O2)4(CH3)4]
Mr925.90
Crystal system, space groupMonoclinic, P2/c
Temperature (K)298
a, b, c (Å)16.4635 (15), 7.5836 (8), 15.1123 (14)
β (°) 115.680 (1)
V (Å3)1700.4 (3)
Z2
Radiation typeMo Kα
µ (mm−1)1.56
Crystal size (mm)0.49 × 0.43 × 0.18
Data collection
DiffractometerBruker SMART CCD area detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.515, 0.766
No. of measured, independent and
observed [I > 2σ(I)] reflections		8140, 2987, 2020
Rint0.059
(sin θ/λ)max (Å−1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.043, 0.127, 1.05
No. of reflections2987
No. of parameters228
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)1.47, −0.76

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SHELXTL (Sheldrick, 2008).

Selected bond lengths (Å) top
Sn1—O12.534 (4)Sn1—O42.155 (4)
Sn1—O22.163 (4)Sn1—C152.093 (6)
Sn1—O32.424 (4)Sn1—C162.088 (6)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C11—H11···F4i0.932.493.326 (8)149
C15—H15B···O4ii0.962.523.474 (8)171
Symmetry codes: (i) −x−1, y, −z−1/2; (ii) −x, −y+1, −z.
 

Acknowledgements

We acknowledge the National Natural Science Foundation of China (20771053) and the Natural Science Foundation of Shandong Province (Y2008B48) for financial support.

References

First citationDuboy, S. K. & Roy, U. (2003). Appl. Organomet. Chem. 17, 3–8.  Web of Science CrossRef Google Scholar
 First citationSheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.  Google Scholar
 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationSiemens (1996). SMART and SAINT. Siemens Analytical X-ray Systems, Inc., Madison, Wisconsin, USA.  Google Scholar
 First citationYin, H.-D., Hong, M., Wang, Q.-B., Xue, S.-C. & Wang, D.-Q. (2005). J. Organomet. Chem. 690, 1669–1676.  Web of Science CSD CrossRef CAS Google Scholar
 First citationYin, H.-D., Wang, C.-H., Wang, Y., Ma, C.-L. & Shao, J.-X. (2003). Chem. J. Chin. Univ. 24, 68–72.  CAS Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

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ISSN: 2056-9890
Volume 67| Part 2| February 2011| Page m148
doi:10.1107/S1600536810054061
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