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Acta Cryst. (2007). E63, m3052    [ doi:10.1107/S1600536807058576 ]

Dichloridotripyridine(triphenylphosphine)ruthenium(II)

R. Kruszynski and J. G. Malecki

Abstract top

All interatomic distances and angles in the title compound, [RuCl2(C5H5N)3(C18H15P)], are normal. The Ru atom is octahedrally and the P atom tetrahedrally coordinated. The structure is stabilized by several weak C-H...Cl intramolecular hydrogen bonds.

Comment top

In the Cambridge Structural Database (Version 5.28 + 3 updates, 01–2007, 05–2007, 08–2007; Allen, 2002) can be found 213 ruthenium complexes containing pyridine (py) in inner coordination sphere (1 compound containing 6 py molecules, 30 compounds containing 5 py molecules, 14 compounds containing 3 py molecules, 55 compounds containing 2 py molecules and 113 compounds containing 1 py molecule), but title compound (I) is the first reported structure containing 3 py molecules and PPh3 subsituent bonded to Ru cation. Additionally, (I) is the first known structure of compound having 3 py molecules and trans arranged halogen atoms.

All intramolecular distances and angles in (I) (Fig. 1) can be considered normal. All atoms lie in general positions. The planes of the phenyl rings of the triphenylphosphine substituent are inclined at 67.93 (6), 67.28 (6) and 59.54 (7)° respectively for pairs of rings indicated by C1/C7, C7/C13 and C1/C13 atoms. The close to planarity pyridine rings are inclined at 66.04 (5), 81.63 (7) and 45.23 (8)° respectively for pairs of rings containing N1/N2, N2/N3 and N1/N3 atoms. The Ru1 atom deviates by 0.098 (3), 0.092 (3) and 0.005 (3)Å from weighted lest squares planes of pyridine rings indicated respectively by N1, N2 and N3 atoms. In the structure can be found several intramolecular C—H···O short contacts (Table 1) which, according to Desiraju & Steiner (1999), can be classified as weak hydrogen bonds. In the structure can not be found any unusual intermolecular interactions.

Related literature top

For related literature, see: Wong & Lau (1994). See also: Allen (2002); Desiraju & Steiner (1999).

Experimental top

The complex was prepared by adding the pyridine salt of 8-hydroxy-2-methyl-quinoline-7-carbodithioic acid to the solution of [RuCl2(PPh3)3] in methanol (100 ml). The reaction mixture was refluxed by 3 h. The crystals of (I) were obtained by slow evaporation of the methanol solution of the complex.

Usage of pyridine instead of its salt leads to [RuCl2(pyridine)4] (Wong and Lau, 1994), thus usage of salt is important.

Refinement top

All hydrogen atoms were placed in calculated positions and were refined as riding on their parent atom with fixed U values [Uiso(H) = 1.2Ueq(C)].

Computing details top

Data collection: CrysAlis CCD (Kuma, 2000); cell refinement: CrysAlis RED (Kuma, 2000); data reduction: CrysAlis RED (Kuma, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP in SHELXTL/PC (Sheldrick, 1990b); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997) and PLATON (Spek, 2003).

Figures top
[Figure 1] Fig. 1. Molecular structure of the title compound. Displacement ellipsoids are drawn at the 50% probability level. Hydrogen atoms are omitted for clarity.
Dichloridotripyridine(triphenylphosphine)ruthenium(II) top
Crystal data top
[RuCl2(C5H5N)3(C18H15P)]Z = 2
Mr = 671.54F000 = 684
Triclinic, P1Dx = 1.542 Mg m−3
Dm = 1.54 Mg m−3
Dm measured by Berman density torsion balance
Hall symbol: -P 1Mo Kα radiation
λ = 0.71073 Å
a = 8.5807 (1) ÅCell parameters from 7117 reflections
b = 10.1447 (1) Åθ = 3–20º
c = 16.9834 (2) ŵ = 0.81 mm−1
α = 78.927 (1)ºT = 291.0 (3) K
β = 85.539 (1)ºPrism, yellow
γ = 89.174 (1)º0.37 × 0.37 × 0.37 mm
V = 1446.46 (3) Å3
Data collection top
Kuma KM4 CCD
diffractometer		5119 independent reflections
Radiation source: fine-focus sealed tube4735 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.019
Detector resolution: 1048576 pixels mm-1θmax = 25.1º
T = 291.0(3) Kθmin = 2.1º
ω scansh = −10→10
Absorption correction: numerical
(X-RED; Stoe & Cie,1999)		k = −9→12
Tmin = 0.720, Tmax = 0.740l = −20→20
14401 measured 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)] = 0.019H-atom parameters constrained
wR(F2) = 0.052  w = 1/[σ2(Fo2) + (0.028P)2 + 0.5954P]
where P = (Fo2 + 2Fc2)/3
S = 1.07(Δ/σ)max = 0.001
5119 reflectionsΔρmax = 0.28 e Å−3
361 parametersΔρmin = −0.61 e Å−3
Primary atom site location: structure-invariant direct methodsExtinction correction: none
Crystal data top
[RuCl2(C5H5N)3(C18H15P)]γ = 89.174 (1)º
Mr = 671.54V = 1446.46 (3) Å3
Triclinic, P1Z = 2
a = 8.5807 (1) ÅMo Kα
b = 10.1447 (1) ŵ = 0.81 mm−1
c = 16.9834 (2) ÅT = 291.0 (3) K
α = 78.927 (1)º0.37 × 0.37 × 0.37 mm
β = 85.539 (1)º
Data collection top
Kuma KM4 CCD
diffractometer		5119 independent reflections
Absorption correction: numerical
(X-RED; Stoe & Cie,1999)		4735 reflections with I > 2σ(I)
Tmin = 0.720, Tmax = 0.740Rint = 0.019
14401 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.019361 parameters
wR(F2) = 0.052H-atom parameters constrained
S = 1.07Δρmax = 0.28 e Å−3
5119 reflectionsΔρmin = −0.61 e Å−3
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 > 2sigma(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
Ru10.616943 (15)0.517519 (12)0.720182 (8)0.02183 (5)
Cl10.78369 (5)0.48535 (5)0.82957 (3)0.03334 (10)
Cl20.44394 (5)0.58568 (4)0.61271 (3)0.03378 (10)
P10.50574 (5)0.31054 (4)0.77488 (3)0.02394 (10)
C10.4244 (2)0.20909 (17)0.70880 (11)0.0278 (4)
C20.4343 (2)0.25245 (18)0.62632 (11)0.0317 (4)
H20.47190.33820.60440.038*
C30.3892 (2)0.1701 (2)0.57575 (12)0.0374 (4)
H30.39850.20000.52030.045*
C40.3307 (2)0.0442 (2)0.60780 (13)0.0412 (5)
H40.2993−0.01090.57410.049*
C50.3188 (3)−0.0001 (2)0.68980 (13)0.0427 (5)
H50.2783−0.08510.71150.051*
C60.3664 (2)0.08047 (18)0.73990 (12)0.0373 (4)
H60.35970.04880.79520.045*
C70.6369 (2)0.17868 (17)0.82475 (11)0.0289 (4)
C80.6343 (3)0.1353 (2)0.90699 (12)0.0426 (5)
H80.56590.17510.94060.051*
C90.7321 (3)0.0333 (2)0.94012 (14)0.0535 (6)
H90.72770.00460.99570.064*
C100.8345 (3)−0.0252 (2)0.89218 (16)0.0571 (6)
H100.9018−0.09210.91470.069*
C110.8376 (3)0.0153 (3)0.81022 (16)0.0623 (7)
H110.9063−0.02510.77700.075*
C120.7388 (3)0.1161 (2)0.77697 (13)0.0469 (5)
H120.74110.14210.72130.056*
C130.3515 (2)0.31553 (17)0.85465 (10)0.0288 (4)
C140.3886 (2)0.37404 (18)0.91916 (11)0.0351 (4)
H140.49060.40160.92180.042*
C150.2764 (3)0.3912 (2)0.97845 (12)0.0457 (5)
H150.30300.42861.02150.055*
C160.1246 (3)0.3530 (2)0.97428 (14)0.0539 (6)
H160.04820.36671.01380.065*
C170.0857 (3)0.2945 (2)0.91187 (15)0.0507 (6)
H17−0.01660.26710.90990.061*
C180.1980 (2)0.2761 (2)0.85205 (12)0.0380 (4)
H180.17050.23700.80980.046*
N10.46188 (17)0.62309 (14)0.78690 (9)0.0270 (3)
C190.5158 (2)0.70417 (18)0.83268 (11)0.0326 (4)
H190.62330.71490.83230.039*
C200.4199 (3)0.7718 (2)0.87986 (12)0.0425 (5)
H200.46220.82720.91040.051*
C210.2598 (3)0.7566 (2)0.88150 (13)0.0477 (5)
H210.19260.79920.91430.057*
C220.2026 (2)0.6768 (2)0.83332 (12)0.0401 (5)
H220.09540.66610.83210.048*
C230.3050 (2)0.61331 (18)0.78716 (11)0.0312 (4)
H230.26460.56080.75430.037*
N20.73976 (17)0.70292 (14)0.67324 (9)0.0283 (3)
C240.6679 (2)0.81775 (18)0.64484 (11)0.0359 (4)
H240.55930.81900.64710.043*
C250.7482 (3)0.9347 (2)0.61224 (13)0.0479 (5)
H250.69431.01320.59340.057*
C260.9085 (3)0.9341 (2)0.60793 (14)0.0535 (6)
H260.96511.01160.58560.064*
C270.9833 (3)0.8172 (2)0.63714 (14)0.0477 (5)
H271.09190.81400.63490.057*
C280.8966 (2)0.7047 (2)0.66977 (12)0.0364 (4)
H280.94870.62610.69040.044*
N30.78249 (16)0.42674 (13)0.64618 (8)0.0252 (3)
C290.7641 (2)0.4297 (2)0.56892 (11)0.0345 (4)
H290.67720.47370.54690.041*
C300.8668 (2)0.3711 (2)0.51992 (13)0.0441 (5)
H300.84730.37310.46660.053*
C310.9988 (3)0.3094 (2)0.55034 (13)0.0462 (5)
H311.07030.26910.51840.055*
C321.0214 (3)0.3092 (2)0.62922 (14)0.0490 (5)
H321.11050.27000.65150.059*
C330.9122 (2)0.3669 (2)0.67520 (13)0.0420 (5)
H330.92860.36440.72890.050*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ru10.02144 (8)0.02457 (8)0.02026 (8)0.00073 (5)−0.00374 (5)−0.00545 (5)
Cl10.0321 (2)0.0429 (2)0.0281 (2)0.00523 (19)−0.01118 (18)−0.01125 (18)
Cl20.0348 (2)0.0379 (2)0.0301 (2)0.00577 (18)−0.01235 (19)−0.00677 (18)
P10.0261 (2)0.0258 (2)0.0202 (2)−0.00026 (17)−0.00340 (17)−0.00459 (16)
C10.0280 (9)0.0282 (9)0.0281 (9)−0.0015 (7)−0.0052 (7)−0.0064 (7)
C20.0344 (10)0.0316 (9)0.0287 (10)−0.0058 (8)−0.0021 (8)−0.0042 (7)
C30.0419 (11)0.0454 (11)0.0265 (10)−0.0058 (9)−0.0037 (8)−0.0095 (8)
C40.0449 (12)0.0423 (11)0.0414 (12)−0.0088 (9)−0.0085 (9)−0.0180 (9)
C50.0531 (13)0.0302 (10)0.0451 (12)−0.0126 (9)−0.0085 (10)−0.0054 (8)
C60.0488 (12)0.0318 (10)0.0304 (10)−0.0068 (8)−0.0080 (9)−0.0012 (8)
C70.0309 (9)0.0259 (9)0.0305 (9)0.0001 (7)−0.0073 (7)−0.0051 (7)
C80.0480 (12)0.0472 (12)0.0313 (11)0.0115 (10)−0.0067 (9)−0.0039 (9)
C90.0639 (15)0.0539 (13)0.0392 (13)0.0129 (12)−0.0143 (11)0.0035 (10)
C100.0589 (15)0.0454 (13)0.0642 (16)0.0213 (11)−0.0177 (12)0.0004 (11)
C110.0671 (16)0.0594 (15)0.0599 (16)0.0329 (13)−0.0034 (13)−0.0131 (12)
C120.0564 (13)0.0479 (12)0.0354 (11)0.0176 (10)−0.0030 (10)−0.0071 (9)
C130.0311 (9)0.0290 (9)0.0234 (9)0.0040 (7)0.0006 (7)0.0009 (7)
C140.0438 (11)0.0333 (10)0.0269 (10)0.0037 (8)−0.0010 (8)−0.0033 (7)
C150.0650 (15)0.0422 (11)0.0264 (10)0.0116 (10)0.0066 (10)−0.0028 (8)
C160.0561 (14)0.0520 (13)0.0424 (13)0.0174 (11)0.0208 (11)0.0076 (10)
C170.0323 (11)0.0548 (13)0.0547 (14)0.0050 (10)0.0076 (10)0.0101 (11)
C180.0322 (10)0.0407 (11)0.0380 (11)0.0022 (8)−0.0028 (8)0.0001 (8)
N10.0302 (8)0.0258 (7)0.0245 (7)0.0019 (6)−0.0021 (6)−0.0037 (6)
C190.0369 (10)0.0318 (9)0.0294 (10)0.0015 (8)−0.0035 (8)−0.0062 (7)
C200.0576 (13)0.0388 (11)0.0329 (11)0.0056 (9)−0.0019 (9)−0.0127 (8)
C210.0517 (13)0.0481 (12)0.0414 (12)0.0135 (10)0.0112 (10)−0.0104 (10)
C220.0327 (10)0.0430 (11)0.0396 (11)0.0058 (8)0.0049 (9)0.0012 (9)
C230.0299 (9)0.0293 (9)0.0323 (10)0.0017 (7)−0.0023 (8)−0.0007 (7)
N20.0303 (8)0.0310 (8)0.0249 (8)−0.0040 (6)0.0002 (6)−0.0087 (6)
C240.0439 (11)0.0320 (10)0.0331 (10)−0.0004 (8)−0.0043 (8)−0.0087 (8)
C250.0719 (16)0.0304 (10)0.0417 (12)−0.0037 (10)−0.0066 (11)−0.0068 (9)
C260.0670 (16)0.0441 (13)0.0489 (13)−0.0274 (11)0.0072 (11)−0.0104 (10)
C270.0430 (12)0.0523 (13)0.0506 (13)−0.0184 (10)0.0042 (10)−0.0186 (10)
C280.0339 (10)0.0405 (10)0.0372 (11)−0.0057 (8)−0.0007 (8)−0.0138 (8)
N30.0240 (7)0.0259 (7)0.0262 (8)−0.0011 (6)−0.0034 (6)−0.0055 (6)
C290.0296 (9)0.0437 (11)0.0305 (10)0.0011 (8)−0.0028 (8)−0.0075 (8)
C300.0421 (12)0.0614 (13)0.0307 (11)0.0039 (10)−0.0018 (9)−0.0144 (10)
C310.0420 (12)0.0554 (13)0.0435 (13)0.0097 (10)0.0042 (10)−0.0192 (10)
C320.0413 (12)0.0644 (14)0.0443 (13)0.0227 (11)−0.0097 (10)−0.0174 (11)
C330.0396 (11)0.0546 (12)0.0347 (11)0.0144 (9)−0.0094 (9)−0.0144 (9)
Geometric parameters (Å, °) top
Ru1—N12.0956 (14)C16—H160.9300
Ru1—N32.1389 (14)C17—C181.382 (3)
Ru1—N22.1527 (14)C17—H170.9300
Ru1—P12.3137 (4)C18—H180.9300
Ru1—Cl12.4026 (4)N1—C191.345 (2)
Ru1—Cl22.4331 (4)N1—C231.350 (2)
P1—C131.8260 (18)C19—C201.372 (3)
P1—C11.8419 (17)C19—H190.9300
P1—C71.8557 (18)C20—C211.382 (3)
C1—C21.381 (3)C20—H200.9300
C1—C61.394 (3)C21—C221.377 (3)
C2—C31.387 (3)C21—H210.9300
C2—H20.9300C22—C231.368 (3)
C3—C41.374 (3)C22—H220.9300
C3—H30.9300C23—H230.9300
C4—C51.375 (3)N2—C241.334 (2)
C4—H40.9300N2—C281.343 (2)
C5—C61.375 (3)C24—C251.379 (3)
C5—H50.9300C24—H240.9300
C6—H60.9300C25—C261.372 (3)
C7—C121.377 (3)C25—H250.9300
C7—C81.380 (3)C26—C271.366 (3)
C8—C91.384 (3)C26—H260.9300
C8—H80.9300C27—C281.372 (3)
C9—C101.358 (3)C27—H270.9300
C9—H90.9300C28—H280.9300
C10—C111.372 (4)N3—C291.328 (2)
C10—H100.9300N3—C331.342 (2)
C11—C121.382 (3)C29—C301.373 (3)
C11—H110.9300C29—H290.9300
C12—H120.9300C30—C311.373 (3)
C13—C181.389 (3)C30—H300.9300
C13—C141.401 (3)C31—C321.368 (3)
C14—C151.372 (3)C31—H310.9300
C14—H140.9300C32—C331.370 (3)
C15—C161.375 (3)C32—H320.9300
C15—H150.9300C33—H330.9300
C16—C171.375 (4)
N1—Ru1—N3174.89 (5)C16—C15—H15120.0
N1—Ru1—N288.61 (5)C17—C16—C15120.1 (2)
N3—Ru1—N286.42 (5)C17—C16—H16119.9
N1—Ru1—P194.11 (4)C15—C16—H16119.9
N3—Ru1—P190.94 (4)C16—C17—C18120.3 (2)
N2—Ru1—P1174.89 (4)C16—C17—H17119.8
N1—Ru1—Cl188.58 (4)C18—C17—H17119.8
N3—Ru1—Cl192.37 (4)C17—C18—C13120.4 (2)
N2—Ru1—Cl187.44 (4)C17—C18—H18119.8
P1—Ru1—Cl188.298 (16)C13—C18—H18119.8
N1—Ru1—Cl285.00 (4)C19—N1—C23116.58 (15)
N3—Ru1—Cl293.51 (4)C19—N1—Ru1120.66 (12)
N2—Ru1—Cl286.29 (4)C23—N1—Ru1122.75 (12)
P1—Ru1—Cl298.252 (16)N1—C19—C20123.20 (18)
Cl1—Ru1—Cl2171.122 (16)N1—C19—H19118.4
C13—P1—C1104.93 (8)C20—C19—H19118.4
C13—P1—C7101.78 (8)C19—C20—C21119.29 (19)
C1—P1—C796.49 (8)C19—C20—H20120.4
C13—P1—Ru1114.03 (6)C21—C20—H20120.4
C1—P1—Ru1119.86 (6)C22—C21—C20118.23 (19)
C7—P1—Ru1116.92 (6)C22—C21—H21120.9
C2—C1—C6118.14 (16)C20—C21—H21120.9
C2—C1—P1120.84 (13)C23—C22—C21119.32 (19)
C6—C1—P1120.67 (14)C23—C22—H22120.3
C1—C2—C3121.03 (17)C21—C22—H22120.3
C1—C2—H2119.5N1—C23—C22123.31 (18)
C3—C2—H2119.5N1—C23—H23118.3
C4—C3—C2119.82 (18)C22—C23—H23118.3
C4—C3—H3120.1C24—N2—C28117.26 (16)
C2—C3—H3120.1C24—N2—Ru1123.23 (13)
C3—C4—C5119.91 (17)C28—N2—Ru1119.49 (12)
C3—C4—H4120.0N2—C24—C25122.68 (19)
C5—C4—H4120.0N2—C24—H24118.7
C6—C5—C4120.30 (18)C25—C24—H24118.7
C6—C5—H5119.8C26—C25—C24119.3 (2)
C4—C5—H5119.8C26—C25—H25120.4
C5—C6—C1120.78 (18)C24—C25—H25120.4
C5—C6—H6119.6C27—C26—C25118.5 (2)
C1—C6—H6119.6C27—C26—H26120.7
C12—C7—C8117.71 (17)C25—C26—H26120.7
C12—C7—P1118.27 (14)C26—C27—C28119.4 (2)
C8—C7—P1123.96 (15)C26—C27—H27120.3
C7—C8—C9121.0 (2)C28—C27—H27120.3
C7—C8—H8119.5N2—C28—C27122.9 (2)
C9—C8—H8119.5N2—C28—H28118.6
C10—C9—C8120.5 (2)C27—C28—H28118.6
C10—C9—H9119.7C29—N3—C33116.77 (16)
C8—C9—H9119.7C29—N3—Ru1121.74 (12)
C9—C10—C11119.4 (2)C33—N3—Ru1121.47 (12)
C9—C10—H10120.3N3—C29—C30123.32 (18)
C11—C10—H10120.3N3—C29—H29118.3
C10—C11—C12120.1 (2)C30—C29—H29118.3
C10—C11—H11119.9C29—C30—C31119.41 (19)
C12—C11—H11119.9C29—C30—H30120.3
C7—C12—C11121.2 (2)C31—C30—H30120.3
C7—C12—H12119.4C32—C31—C30117.79 (19)
C11—C12—H12119.4C32—C31—H31121.1
C18—C13—C14118.24 (18)C30—C31—H31121.1
C18—C13—P1124.34 (14)C31—C32—C33119.72 (19)
C14—C13—P1117.18 (14)C31—C32—H32120.1
C15—C14—C13120.9 (2)C33—C32—H32120.1
C15—C14—H14119.6N3—C33—C32122.95 (19)
C13—C14—H14119.6N3—C33—H33118.5
C14—C15—C16120.0 (2)C32—C33—H33118.5
C14—C15—H15120.0
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C2—H2···Cl20.932.553.3456 (18)144
C19—H19···Cl10.932.693.1771 (19)113
C23—H23···Cl20.932.723.1681 (19)110
C24—H24···Cl20.932.763.2128 (19)111
C28—H28···Cl10.932.813.254 (2)111
C29—H29···Cl20.932.573.257 (2)131
C33—H33···Cl10.932.533.203 (2)129
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C2—H2···Cl20.932.553.3456 (18)144
C19—H19···Cl10.932.693.1771 (19)113
C23—H23···Cl20.932.723.1681 (19)110
C24—H24···Cl20.932.763.2128 (19)111
C28—H28···Cl10.932.813.254 (2)111
C29—H29···Cl20.932.573.257 (2)131
C33—H33···Cl10.932.533.203 (2)129
references
References top

Allen, F. H. (2002). Acta Cryst. B58, 380–388.

Desiraju, G. R. & Steiner, T. (1999). The Weak Hydrogen Bond in Structural Chemistry and Biology. IUCr Monograph on Crystallography 9. Oxford University Press.

Kuma (2000). CrysAlis CCD and CrysAlis RED. Versions 1.163. Kuma Diffraction Instruments GmbH, Wrocław, Poland.

Sheldrick, G. M. (1990a). Acta Cryst. A46, 467–473.

Sheldrick, G. M. (1990b). SHELXTL/PC. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.

Sheldrick, G. M. (1997). SHELXL97. University of Göttingen, Germany

Spek, A. L. (2003). J. Appl. Cryst. 36, 7–13.

Stoe & Cie (1999). X-RED. Version 1.18. Stoe & Cie GmbH, Darmstadt, Germany.

Wong, W.-T. & Lau, T.-C. (1994). Acta Cryst. C50, 1406–1407.