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

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ISSN: 2056-9890

trans-Bis[1-(2-anilino-2-oxoeth­yl)-3-benzyl-1H-imidazol-2-yl]palladium(II) methanol disolvate

aNational Changhua University of Education, Department of Chemistry, Changhua, Taiwan 50058
*Correspondence e-mail: leehm@cc.ncue.edu.tw

(Received 17 February 2011; accepted 1 March 2011; online 19 March 2011)

In the title compound, [Pd(C18H16N3O)2]·2CH3OH, the PdII atom is located on a crystallographic inversion center. It has a square-planar coordination geometry, with the two bidentate ligands coordinated in a trans fashion via the carbene C atom and the amido N atoms. The methanol solvent mol­ecules form O—H⋯O hydrogen bonds with the complex. Additional non-classical inter­molecular C—H⋯O hydrogen bonds link the complexes into a two-dimensional network parallel to (001).

Related literature

Palladium complexes with multidentate ligands containing N-heterocyclic carbene and anionic amidate functionalities attract inter­est because of their effectiveness in catalysing C—C coupling reactions, see: Liao et al. (2007[Liao, C.-Y., Chan, K.-T., Zeng, J.-Y., Hu, C.-H., Tu, C.-Y. & Lee, H. M. (2007). Organometallics, 26, 1692-1702.]); Sakaguchi et al. (2008[Sakaguchi, S., Yoo, K., O'Neill, J., Lee, J., Stewart, T. & Jung, K. (2008). Angew. Chem. Int. Ed. 47, 9326-9329.]).

[Scheme 1]

Experimental

Crystal data
  • [Pd(C18H16N3O)2]·2CH4O

  • Mr = 751.16

  • Orthorhombic, P b c a

  • a = 17.822 (2) Å

  • b = 9.0616 (11) Å

  • c = 21.473 (3) Å

  • V = 3467.8 (7) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.59 mm−1

  • T = 150 K

  • 0.39 × 0.09 × 0.08 mm

Data collection
  • Bruker SMART APEXII diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 2003[Sheldrick, G. M. (2003). SADABS. University of Göttingen, Germany.]) Tmin = 0.804, Tmax = 0.955

  • 45827 measured reflections

  • 4451 independent reflections

  • 2695 reflections with I > 2σ

  • Rint = 0.080

Refinement
  • R[F2 > 2σ(F2)] = 0.032

  • wR(F2) = 0.084

  • S = 1.00

  • 4451 reflections

  • 224 parameters

  • H-atom parameters constrained

  • Δρmax = 0.39 e Å−3

  • Δρmin = −0.67 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O2—H1⋯O1i 0.92 1.81 2.727 (3) 172
C2—H2⋯O1ii 0.95 2.36 3.232 (3) 152
C18—H18⋯O1 0.95 2.32 2.842 (3) 114
Symmetry codes: (i) [x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]; (ii) [-x+{\script{1\over 2}}, y-{\script{1\over 2}}, z].

Data collection: APEX2 (Bruker, 2007[Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). APEX2 and SAINT. Bruker AXS 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: DIAMOND (Brandenburg, 2006[Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany.]).

Supporting information


Comment top

Palladium complexes with multidentate ligands containing N-heterocyclic carbene and anionic amidate functionalities attract interest because of their effectiveness in catalyzing C—C coupling reactions (Liao et al., 2007 and Sakaguchi et al., 2008). The crystal structure of the title compound consists of such palladium carbene complex with two solvated methanol molecules incorporated. The structure of a DMSO solvate of the same trans compound, C36H32N6O2Pd.4C2H6SO, was reported by us previously (Liao et al., 2007)

The palladium atom adopts square coordination geometry with two trans coordinated bidentate ligands. The structure of the cis isomer, C36H32N6O2Pd.2CH3OH, was also reported earlier (Liao et al., 2007). A comparison of the geometric parameters of the trans and cis isomers shows that the Pd—C bond distance in the trans isomer is longer than that in the cis isomer [2.014 (2) vs. 1.966 (2) Å]. Contrastingly, the Pd—N bond distance is shorter in the trans isomer [2.051 (2) vs. 2.087 (1) Å].

Related literature top

Palladium complexes with multidentate ligands containing N-heterocyclic carbene and anionic amidate functionalities attract interest because of their effectiveness in catalysing C—C coupling reactions, see: Liao et al. (2007); Sakaguchi et al. (2008).

Experimental top

The title compound was prepared according to the literature procedure (Liao et al., 2007). Colorless crystals suitable for X-ray diffraction analysis were grown by slow evaporation of a methanol solution containing the compound.

Refinement top

All the H atoms were positioned geometrically and refined as riding atoms, with Caryl—H = 0.95, Cmethylene —H = 0.99, and Cmethyl —H = 0.98 Å while Uiso(H) = 1.2Ueq(Cmethine), Uiso(H) = 1.2Ueq(Cmethylene), and Uiso(H) = 1.5 Ueq (Cmethyl). H1 bound to oxygen was found in the difference Fourier map, not refined and with Uiso(H) = 1.2Ueq(O).

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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: DIAMOND (Brandenburg, 2006).

Figures top
[Figure 1] Fig. 1. The structure of the title complex, showing 50% displacement ellipsoids. H atoms are excluded for clarity. [Symmetry code: (i) 1 - x, 1 - y, 2 - z. (ii) x, 1/2 - y, 1/2 + z.]
[Figure 2] Fig. 2. A view of the crystal packing along the c axis, displaying the hydrogen bonds as dashed lines.
trans-Bis[1-(2-anilino-2-oxoethyl)-3-benzyl-1H- imidazol-2-yl]palladium(II) methanol disolvate top
Crystal data top
[Pd(C18H16N3O)2]·2CH4OF(000) = 1552
Mr = 751.16Dx = 1.439 Mg m3
Orthorhombic, PbcaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 3616 reflections
a = 17.822 (2) Åθ = 2.7–22.4°
b = 9.0616 (11) ŵ = 0.59 mm1
c = 21.473 (3) ÅT = 150 K
V = 3467.8 (7) Å3Parallelpiped, white
Z = 40.39 × 0.09 × 0.08 mm
Data collection top
Bruker SMART APEXII
diffractometer
4451 independent reflections
Radiation source: fine-focus sealed tube2695 reflections with I > 2σ
Graphite monochromatorRint = 0.080
ω scansθmax = 28.7°, θmin = 1.9°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)
h = 2123
Tmin = 0.804, Tmax = 0.955k = 1212
45827 measured reflectionsl = 2828
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)] = 0.032Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.084H-atom parameters constrained
S = 1.00 w = 1/[σ2(Fo2) + (0.0273P)2 + 3.0876P]
where P = (Fo2 + 2Fc2)/3
4451 reflections(Δ/σ)max = 0.001
224 parametersΔρmax = 0.39 e Å3
0 restraintsΔρmin = 0.67 e Å3
Crystal data top
[Pd(C18H16N3O)2]·2CH4OV = 3467.8 (7) Å3
Mr = 751.16Z = 4
Orthorhombic, PbcaMo Kα radiation
a = 17.822 (2) ŵ = 0.59 mm1
b = 9.0616 (11) ÅT = 150 K
c = 21.473 (3) Å0.39 × 0.09 × 0.08 mm
Data collection top
Bruker SMART APEXII
diffractometer
4451 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)
2695 reflections with I > 2σ
Tmin = 0.804, Tmax = 0.955Rint = 0.080
45827 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0320 restraints
wR(F2) = 0.084H-atom parameters constrained
S = 1.00Δρmax = 0.39 e Å3
4451 reflectionsΔρmin = 0.67 e Å3
224 parameters
Special details top

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) top
xyzUiso*/Ueq
C10.46400 (13)0.2896 (2)0.99551 (11)0.0171 (5)
C20.38152 (15)0.1075 (3)1.01712 (12)0.0228 (6)
H20.34180.05451.03630.027*
C30.42383 (14)0.0630 (3)0.96912 (13)0.0226 (6)
H30.41980.02840.94770.027*
C40.52739 (16)0.1767 (3)0.90363 (11)0.0219 (5)
H4A0.53390.07480.88790.026*
H4B0.57690.21240.91810.026*
C50.49996 (16)0.2745 (3)0.85115 (11)0.0217 (5)
C60.42429 (16)0.2778 (3)0.83425 (12)0.0280 (6)
H60.38900.21910.85630.034*
C70.40060 (18)0.3664 (3)0.78546 (13)0.0350 (7)
H70.34910.36760.77400.042*
C80.45124 (19)0.4528 (3)0.75345 (14)0.0385 (8)
H80.43470.51330.72000.046*
C90.5260 (2)0.4511 (4)0.77007 (14)0.0389 (8)
H90.56090.51110.74820.047*
C100.55057 (17)0.3619 (3)0.81869 (13)0.0300 (6)
H100.60220.36080.82970.036*
C110.37610 (15)0.3458 (3)1.07994 (11)0.0211 (6)
H11A0.41530.36971.11100.025*
H11B0.33470.29471.10190.025*
C120.34608 (14)0.4900 (3)1.05140 (11)0.0181 (5)
C130.35913 (13)0.6589 (2)0.96519 (11)0.0165 (5)
C140.39053 (15)0.6620 (3)0.90513 (12)0.0222 (6)
H140.43110.59790.89550.027*
C150.36355 (16)0.7567 (3)0.85971 (12)0.0286 (6)
H150.38590.75760.81950.034*
C160.30402 (16)0.8504 (3)0.87279 (13)0.0296 (6)
H160.28460.91400.84150.036*
C170.27323 (16)0.8499 (3)0.93189 (13)0.0279 (6)
H170.23270.91450.94110.033*
C180.30045 (14)0.7565 (3)0.97816 (13)0.0229 (5)
H180.27910.75921.01870.027*
C190.2385 (2)0.1346 (5)0.70995 (15)0.0574 (10)
H19A0.25220.23320.69500.086*
H19B0.28420.07700.71750.086*
H19C0.21000.14340.74880.086*
N10.40758 (11)0.2469 (2)1.03309 (9)0.0182 (4)
N20.47490 (12)0.1753 (2)0.95629 (9)0.0184 (4)
N30.38849 (11)0.5529 (2)1.00742 (9)0.0174 (4)
O10.28388 (10)0.5348 (2)1.07073 (8)0.0254 (4)
Pd10.50000.50001.00000.01396 (7)
O20.19462 (14)0.0636 (3)0.66513 (12)0.0650 (8)
H10.22450.03840.63160.078*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0130 (12)0.0172 (11)0.0210 (11)0.0014 (9)0.0003 (11)0.0020 (10)
C20.0202 (13)0.0146 (12)0.0335 (14)0.0036 (11)0.0002 (11)0.0052 (10)
C30.0199 (14)0.0127 (11)0.0351 (15)0.0028 (11)0.0030 (12)0.0006 (11)
C40.0214 (13)0.0206 (12)0.0236 (13)0.0043 (11)0.0040 (11)0.0034 (11)
C50.0279 (14)0.0172 (11)0.0200 (11)0.0047 (12)0.0003 (12)0.0033 (9)
C60.0303 (16)0.0269 (15)0.0268 (14)0.0002 (12)0.0007 (12)0.0009 (12)
C70.0358 (18)0.0377 (17)0.0314 (15)0.0086 (14)0.0057 (13)0.0001 (13)
C80.051 (2)0.0376 (16)0.0266 (15)0.0098 (16)0.0003 (14)0.0056 (13)
C90.049 (2)0.0359 (16)0.0319 (16)0.0023 (15)0.0117 (15)0.0086 (14)
C100.0300 (16)0.0317 (15)0.0282 (14)0.0001 (13)0.0055 (12)0.0008 (12)
C110.0200 (14)0.0221 (13)0.0212 (12)0.0009 (11)0.0073 (11)0.0041 (10)
C120.0157 (12)0.0183 (12)0.0203 (11)0.0023 (11)0.0004 (9)0.0031 (11)
C130.0125 (12)0.0133 (11)0.0237 (13)0.0028 (9)0.0009 (10)0.0022 (10)
C140.0209 (14)0.0197 (13)0.0258 (13)0.0026 (11)0.0010 (11)0.0041 (11)
C150.0343 (17)0.0304 (15)0.0212 (13)0.0010 (13)0.0057 (12)0.0004 (11)
C160.0339 (17)0.0219 (14)0.0331 (15)0.0031 (12)0.0119 (13)0.0043 (12)
C170.0205 (15)0.0213 (13)0.0418 (16)0.0038 (11)0.0023 (12)0.0013 (12)
C180.0191 (13)0.0178 (12)0.0317 (13)0.0013 (11)0.0025 (11)0.0006 (11)
C190.053 (2)0.082 (3)0.0367 (18)0.011 (2)0.0133 (17)0.0195 (19)
N10.0152 (10)0.0156 (10)0.0238 (11)0.0014 (9)0.0028 (9)0.0021 (8)
N20.0186 (11)0.0153 (10)0.0213 (10)0.0001 (8)0.0011 (9)0.0023 (9)
N30.0112 (10)0.0166 (8)0.0245 (11)0.0006 (8)0.0019 (8)0.0005 (8)
O10.0169 (10)0.0312 (10)0.0279 (9)0.0047 (8)0.0069 (8)0.0044 (8)
Pd10.01066 (11)0.01262 (11)0.01860 (11)0.00022 (11)0.00200 (11)0.00015 (11)
O20.0374 (15)0.104 (2)0.0534 (15)0.0128 (15)0.0180 (12)0.0321 (15)
Geometric parameters (Å, º) top
C1—N11.346 (3)C11—H11A0.9900
C1—N21.349 (3)C11—H11B0.9900
C1—Pd12.014 (2)C12—O11.252 (3)
C2—C31.339 (4)C12—N31.337 (3)
C2—N11.388 (3)C13—C181.398 (3)
C2—H20.9500C13—C141.406 (3)
C3—N21.393 (3)C13—N31.421 (3)
C3—H30.9500C14—C151.385 (4)
C4—N21.468 (3)C14—H140.9500
C4—C51.515 (3)C15—C161.387 (4)
C4—H4A0.9900C15—H150.9500
C4—H4B0.9900C16—C171.383 (4)
C5—C101.388 (4)C16—H160.9500
C5—C61.397 (4)C17—C181.392 (4)
C6—C71.386 (4)C17—H170.9500
C6—H60.9500C18—H180.9500
C7—C81.378 (4)C19—O21.397 (4)
C7—H70.9500C19—H19A0.9800
C8—C91.379 (5)C19—H19B0.9800
C8—H80.9500C19—H19C0.9800
C9—C101.391 (4)N3—Pd12.050 (2)
C9—H90.9500Pd1—C1i2.014 (2)
C10—H100.9500Pd1—N3i2.051 (2)
C11—N11.460 (3)O2—H10.9244
C11—C121.540 (3)
N1—C1—N2105.1 (2)N3—C12—C11116.5 (2)
N1—C1—Pd1118.80 (17)C18—C13—C14117.9 (2)
N2—C1—Pd1135.30 (18)C18—C13—N3125.2 (2)
C3—C2—N1106.0 (2)C14—C13—N3116.9 (2)
C3—C2—H2127.0C15—C14—C13121.3 (2)
N1—C2—H2127.0C15—C14—H14119.3
C2—C3—N2107.5 (2)C13—C14—H14119.3
C2—C3—H3126.3C14—C15—C16120.1 (3)
N2—C3—H3126.3C14—C15—H15119.9
N2—C4—C5111.9 (2)C16—C15—H15119.9
N2—C4—H4A109.2C17—C16—C15119.2 (3)
C5—C4—H4A109.2C17—C16—H16120.4
N2—C4—H4B109.2C15—C16—H16120.4
C5—C4—H4B109.2C16—C17—C18121.2 (3)
H4A—C4—H4B107.9C16—C17—H17119.4
C10—C5—C6119.0 (2)C18—C17—H17119.4
C10—C5—C4119.9 (3)C17—C18—C13120.2 (3)
C6—C5—C4121.1 (2)C17—C18—H18119.9
C7—C6—C5120.2 (3)C13—C18—H18119.9
C7—C6—H6119.9O2—C19—H19A109.5
C5—C6—H6119.9O2—C19—H19B109.5
C8—C7—C6120.4 (3)H19A—C19—H19B109.5
C8—C7—H7119.8O2—C19—H19C109.5
C6—C7—H7119.8H19A—C19—H19C109.5
C7—C8—C9119.8 (3)H19B—C19—H19C109.5
C7—C8—H8120.1C1—N1—C2111.3 (2)
C9—C8—H8120.1C1—N1—C11121.6 (2)
C8—C9—C10120.3 (3)C2—N1—C11126.9 (2)
C8—C9—H9119.8C1—N2—C3110.1 (2)
C10—C9—H9119.8C1—N2—C4124.5 (2)
C5—C10—C9120.2 (3)C3—N2—C4125.1 (2)
C5—C10—H10119.9C12—N3—C13122.0 (2)
C9—C10—H10119.9C12—N3—Pd1120.21 (16)
N1—C11—C12112.36 (19)C13—N3—Pd1117.74 (15)
N1—C11—H11A109.1C1i—Pd1—C1179.999 (1)
C12—C11—H11A109.1C1i—Pd1—N394.81 (9)
N1—C11—H11B109.1C1—Pd1—N385.19 (9)
C12—C11—H11B109.1C1i—Pd1—N3i85.19 (9)
H11A—C11—H11B107.9C1—Pd1—N3i94.81 (9)
O1—C12—N3126.6 (2)N3—Pd1—N3i179.999 (1)
O1—C12—C11116.8 (2)C19—O2—H1109.1
N1—C2—C3—N20.1 (3)C12—C11—N1—C157.6 (3)
N2—C4—C5—C10140.4 (2)C12—C11—N1—C2116.4 (3)
N2—C4—C5—C640.1 (3)N1—C1—N2—C31.2 (3)
C10—C5—C6—C70.5 (4)Pd1—C1—N2—C3168.1 (2)
C4—C5—C6—C7179.0 (2)N1—C1—N2—C4175.0 (2)
C5—C6—C7—C80.4 (4)Pd1—C1—N2—C45.7 (4)
C6—C7—C8—C90.0 (5)C2—C3—N2—C10.7 (3)
C7—C8—C9—C100.4 (5)C2—C3—N2—C4174.4 (2)
C6—C5—C10—C90.1 (4)C5—C4—N2—C171.5 (3)
C4—C5—C10—C9179.4 (2)C5—C4—N2—C3101.4 (3)
C8—C9—C10—C50.4 (4)O1—C12—N3—C1316.9 (4)
N1—C11—C12—O1136.3 (2)C11—C12—N3—C13161.5 (2)
N1—C11—C12—N342.3 (3)O1—C12—N3—Pd1162.1 (2)
C18—C13—C14—C151.1 (4)C11—C12—N3—Pd119.5 (3)
N3—C13—C14—C15177.1 (2)C18—C13—N3—C1230.0 (4)
C13—C14—C15—C160.5 (4)C14—C13—N3—C12148.0 (2)
C14—C15—C16—C171.3 (4)C18—C13—N3—Pd1149.0 (2)
C15—C16—C17—C180.5 (4)C14—C13—N3—Pd132.9 (3)
C16—C17—C18—C131.1 (4)N1—C1—Pd1—N340.62 (19)
C14—C13—C18—C171.9 (4)N2—C1—Pd1—N3127.6 (3)
N3—C13—C18—C17176.1 (2)N1—C1—Pd1—N3i139.37 (19)
N2—C1—N1—C21.3 (3)N2—C1—Pd1—N3i52.4 (3)
Pd1—C1—N1—C2170.12 (17)C12—N3—Pd1—C1i126.10 (19)
N2—C1—N1—C11176.1 (2)C13—N3—Pd1—C1i52.97 (18)
Pd1—C1—N1—C114.7 (3)C12—N3—Pd1—C153.90 (19)
C3—C2—N1—C10.9 (3)C13—N3—Pd1—C1127.03 (18)
C3—C2—N1—C11175.4 (2)
Symmetry code: (i) x+1, y+1, z+2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H1···O1ii0.921.812.727 (3)172
C2—H2···O1iii0.952.363.232 (3)152
C18—H18···O10.952.322.842 (3)114
Symmetry codes: (ii) x, y+1/2, z1/2; (iii) x+1/2, y1/2, z.

Experimental details

Crystal data
Chemical formula[Pd(C18H16N3O)2]·2CH4O
Mr751.16
Crystal system, space groupOrthorhombic, Pbca
Temperature (K)150
a, b, c (Å)17.822 (2), 9.0616 (11), 21.473 (3)
V3)3467.8 (7)
Z4
Radiation typeMo Kα
µ (mm1)0.59
Crystal size (mm)0.39 × 0.09 × 0.08
Data collection
DiffractometerBruker SMART APEXII
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 2003)
Tmin, Tmax0.804, 0.955
No. of measured, independent and
observed (I > 2σ) reflections
45827, 4451, 2695
Rint0.080
(sin θ/λ)max1)0.675
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.032, 0.084, 1.00
No. of reflections4451
No. of parameters224
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.39, 0.67

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXTL (Sheldrick, 2008), DIAMOND (Brandenburg, 2006).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H1···O1i0.921.812.727 (3)172
C2—H2···O1ii0.952.363.232 (3)152
C18—H18···O10.952.322.842 (3)114
Symmetry codes: (i) x, y+1/2, z1/2; (ii) x+1/2, y1/2, z.
 

Acknowledgements

We are grateful to the National Science Council of Taiwan for financial support of this work.

References

First citationBrandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany.  Google Scholar
First citationBruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationLiao, C.-Y., Chan, K.-T., Zeng, J.-Y., Hu, C.-H., Tu, C.-Y. & Lee, H. M. (2007). Organometallics, 26, 1692–1702.  Web of Science CSD CrossRef CAS Google Scholar
First citationSakaguchi, S., Yoo, K., O'Neill, J., Lee, J., Stewart, T. & Jung, K. (2008). Angew. Chem. Int. Ed. 47, 9326–9329.  CrossRef CAS Google Scholar
First citationSheldrick, G. M. (2003). 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

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