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The title complex, [Ru(C2H3N)2(C6H6N2)(C18H15P)2](PF6)2.CH4O, is the third of a series of ruthenium complexes containing two tri­phenyl­phosphine groups in a trans arrangement, o-benzoquinone di­imine and two other non-redox active ligands to been characterized. The effect of electron donor-acceptor properties of the two non-redox active ligands does not change the quinone arrangement for the o-benzoquinone di­imine ligand, as can be seen from the bond distances of the quinone ring. The asymmetric unit contains half a mol­ecule of complex cation (on a twofold rotation axis), one hexa­fluoro­phosphate anion and half a mol­ecule of methanol in a general position close to a twofold rotation axis.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270100007654/qa0305sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270100007654/qa0305Isup2.hkl
Contains datablock I

CCDC reference: 147684

Comment top

In order to evaluate the effect of electron density on the quinone ligand and its effect on the possible quinone or semiquinone arrangement, we have synthesized a family of complexes which have different non-redox active ligands in the same plane as the o-benzoquinone diimine (BQDI). The bond distances in the BQDI ring for a complex with two electron-donor ligands, such as chloride (Venegas-Yazigi et al., 2000b), one electron donor (chloride) and one electron-acceptor ligand (acetonitrile) (Venegas-Yazigi et al., 2000a), and the title compund, (I), with two electron-acceptor ligands (acetonitrile) show a quinone arrangement for the BQDI ring.

Experimental top

No text provided.

Refinement top

The structure appears to be a racemic twin.

Computing details top

Data collection: KappaCCD Server Software (Nonius, 1997); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO-SMN; program(s) used to solve structure: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL; software used to prepare material for publication: SHELXTL.

Bis(acetonitrile-N)(o-benzoquinone diimine-N,N')-trans-bis(triphenyl- phosphine-P)ruthenium(II) hexafluorophosphate methanol solvate top
Crystal data top
[Ru(C2H3N)2(C6H6N2)(C18H15P)2](PF6)2·CH4OF(000) = 2304
Mr = 1135.83Dx = 1.547 Mg m3
Orthorhombic, Aba2Mo Kα radiation, λ = 0.71073 Å
Hall symbol: A 2 -2abCell parameters from 14495 reflections
a = 19.0603 (5) Åθ = 4.2–23.7°
b = 16.5960 (4) ŵ = 0.54 mm1
c = 15.4192 (3) ÅT = 100 K
V = 4877.5 (2) Å3Block cut from needle, purple
Z = 40.39 × 0.38 × 0.31 mm
Data collection top
Nonius KappaCCD
diffractometer
4778 independent reflections
Radiation source: fine-focus sealed tube4410 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.049
ϕ and ω scans with κ offsetsθmax = 26.4°, θmin = 4.2°
Absorption correction: multi-scan
(DENZO-SMN; Otwinowski & Minor, 1997)
h = 2323
Tmin = 0.817, Tmax = 0.851k = 2020
14495 measured reflectionsl = 1919
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)] = 0.027H-atom parameters constrained
wR(F2) = 0.073 w = 1/[σ2(Fo2) + (0.0342P)2 + 4.8593P]
where P = (Fo2 + 2Fc2)/3
S = 1.07(Δ/σ)max = 0.001
4778 reflectionsΔρmax = 0.43 e Å3
325 parametersΔρmin = 0.25 e Å3
1 restraintAbsolute structure: Flack (1983), 2205 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.52 (3)
Crystal data top
[Ru(C2H3N)2(C6H6N2)(C18H15P)2](PF6)2·CH4OV = 4877.5 (2) Å3
Mr = 1135.83Z = 4
Orthorhombic, Aba2Mo Kα radiation
a = 19.0603 (5) ŵ = 0.54 mm1
b = 16.5960 (4) ÅT = 100 K
c = 15.4192 (3) Å0.39 × 0.38 × 0.31 mm
Data collection top
Nonius KappaCCD
diffractometer
4778 independent reflections
Absorption correction: multi-scan
(DENZO-SMN; Otwinowski & Minor, 1997)
4410 reflections with I > 2σ(I)
Tmin = 0.817, Tmax = 0.851Rint = 0.049
14495 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.027H-atom parameters constrained
wR(F2) = 0.073Δρmax = 0.43 e Å3
S = 1.07Δρmin = 0.25 e Å3
4778 reflectionsAbsolute structure: Flack (1983), 2205 Friedel pairs
325 parametersAbsolute structure parameter: 0.52 (3)
1 restraint
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*/UeqOcc. (<1)
Ru10.00000.00000.37103 (3)0.02033 (7)
P10.03583 (3)0.13908 (3)0.37209 (6)0.02250 (12)
P20.28798 (4)0.06658 (5)0.32065 (6)0.03187 (17)
F10.25220 (11)0.00277 (10)0.3770 (3)0.0539 (5)
F20.32288 (12)0.13505 (13)0.26411 (14)0.0568 (6)
F30.31591 (12)0.00030 (11)0.25543 (14)0.0468 (5)
F40.35729 (10)0.05864 (14)0.3768 (2)0.0636 (6)
F50.25840 (11)0.13238 (12)0.38648 (15)0.0515 (6)
F60.21771 (10)0.07433 (14)0.26339 (16)0.0563 (6)
N10.06236 (13)0.02523 (16)0.26943 (17)0.0235 (5)
H1A0.10560.04250.27680.028*
N20.07600 (14)0.02450 (17)0.46141 (17)0.0262 (5)
C10.03598 (14)0.01483 (15)0.19195 (18)0.0244 (6)
C20.07065 (16)0.03035 (18)0.11102 (19)0.0300 (6)
H2A0.11750.04990.10980.036*
C30.03505 (19)0.0165 (2)0.0366 (2)0.0359 (8)
H30.05680.02880.01730.043*
C40.12267 (15)0.03700 (19)0.50579 (19)0.0296 (6)
C50.18201 (19)0.0523 (3)0.5623 (2)0.0549 (10)
H5A0.22430.06040.52710.082*
H5B0.17290.10060.59700.082*
H5C0.18890.00600.60090.082*
C110.08813 (16)0.17132 (19)0.4648 (2)0.0265 (6)
C120.06463 (16)0.14962 (18)0.54766 (19)0.0301 (6)
H12A0.02610.11370.55350.036*
C130.0969 (2)0.1799 (2)0.6210 (2)0.0355 (8)
H13A0.08070.16460.67690.043*
C140.15288 (18)0.2324 (2)0.6127 (2)0.0399 (8)
H14A0.17490.25360.66310.048*
C150.17679 (18)0.2539 (2)0.5321 (2)0.0414 (8)
H15A0.21560.28960.52700.050*
C160.14470 (17)0.2240 (2)0.4577 (2)0.0367 (7)
H16A0.16140.23950.40200.044*
C210.08659 (17)0.15953 (18)0.2748 (2)0.0265 (6)
C220.05346 (16)0.19109 (18)0.2017 (2)0.0317 (6)
H22A0.00610.20880.20510.038*
C230.0901 (2)0.1965 (2)0.1234 (2)0.0398 (8)
H23A0.06760.21810.07360.048*
C240.15847 (19)0.1707 (2)0.1181 (2)0.0434 (8)
H24A0.18320.17480.06480.052*
C250.19127 (16)0.13897 (19)0.1900 (2)0.0380 (7)
H25A0.23860.12140.18590.046*
C260.15598 (15)0.13236 (18)0.2681 (2)0.0317 (6)
H26A0.17880.10950.31710.038*
C310.03068 (12)0.21894 (13)0.3703 (3)0.0265 (5)
C320.10196 (13)0.20295 (15)0.3668 (3)0.0302 (5)
H32A0.11810.14880.36470.036*
C330.14995 (15)0.26648 (17)0.3665 (3)0.0386 (6)
H33A0.19880.25540.36430.046*
C340.12703 (16)0.34472 (16)0.3692 (3)0.0424 (7)
H34A0.15990.38770.36990.051*
C350.05592 (17)0.36081 (16)0.3710 (3)0.0433 (7)
H35A0.04000.41510.37110.052*
C360.00769 (14)0.29849 (15)0.3727 (4)0.0371 (6)
H36A0.04110.31000.37550.045*
O1S0.0285 (7)0.0146 (6)0.6929 (8)0.111 (4)0.50
H1S0.05170.00130.73600.166*0.50
C1S0.0408 (7)0.0844 (14)0.6798 (10)0.131 (7)0.50
H1S10.00020.11700.69690.196*0.50
H1S20.08190.10070.71390.196*0.50
H1S30.05040.09250.61800.196*0.50
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ru10.01824 (12)0.02177 (12)0.02098 (13)0.00139 (10)0.0000.000
P10.0214 (3)0.0218 (3)0.0243 (3)0.0009 (2)0.0009 (4)0.0003 (4)
P20.0266 (3)0.0326 (4)0.0364 (4)0.0020 (3)0.0015 (3)0.0018 (3)
F10.0688 (12)0.0426 (9)0.0504 (13)0.0097 (9)0.0181 (17)0.0006 (11)
F20.0632 (14)0.0508 (12)0.0564 (13)0.0195 (11)0.0022 (11)0.0120 (10)
F30.0545 (13)0.0478 (12)0.0382 (11)0.0117 (9)0.0053 (9)0.0003 (8)
F40.0463 (11)0.0832 (15)0.0611 (13)0.0068 (10)0.0244 (14)0.0054 (15)
F50.0588 (12)0.0429 (10)0.0528 (15)0.0037 (9)0.0012 (10)0.0084 (9)
F60.0346 (11)0.0662 (14)0.0681 (14)0.0029 (10)0.0187 (10)0.0074 (11)
N10.0193 (12)0.0218 (11)0.0294 (13)0.0033 (10)0.0009 (10)0.0007 (10)
N20.0305 (14)0.0247 (12)0.0234 (13)0.0021 (11)0.0006 (11)0.0023 (10)
C10.0244 (15)0.0246 (13)0.0243 (14)0.0014 (10)0.0002 (11)0.0009 (10)
C20.0282 (14)0.0326 (15)0.0292 (15)0.0038 (12)0.0057 (12)0.0012 (12)
C30.040 (2)0.0457 (18)0.0217 (16)0.0048 (15)0.0002 (14)0.0029 (14)
C40.0288 (15)0.0373 (16)0.0228 (14)0.0061 (12)0.0018 (12)0.0029 (12)
C50.0372 (19)0.093 (3)0.0344 (19)0.0191 (19)0.0145 (15)0.0105 (19)
C110.0235 (15)0.0275 (14)0.0285 (15)0.0032 (12)0.0042 (13)0.0013 (13)
C120.0290 (14)0.0305 (14)0.0308 (15)0.0018 (12)0.0008 (12)0.0003 (13)
C130.041 (2)0.0379 (17)0.0279 (16)0.0058 (14)0.0019 (14)0.0021 (15)
C140.0407 (17)0.043 (2)0.0357 (18)0.0026 (14)0.0143 (14)0.0064 (16)
C150.0386 (17)0.0447 (18)0.0407 (18)0.0113 (14)0.0111 (14)0.0014 (14)
C160.0343 (16)0.0402 (17)0.0357 (16)0.0075 (14)0.0067 (13)0.0019 (13)
C210.0272 (15)0.0224 (14)0.0299 (16)0.0016 (12)0.0009 (13)0.0009 (12)
C220.0309 (15)0.0328 (15)0.0313 (15)0.0039 (13)0.0030 (12)0.0012 (13)
C230.048 (2)0.049 (2)0.0224 (15)0.0045 (17)0.0007 (15)0.0072 (15)
C240.046 (2)0.048 (2)0.0354 (17)0.0095 (16)0.0128 (15)0.0003 (16)
C250.0305 (15)0.0417 (17)0.0418 (18)0.0009 (13)0.0115 (13)0.0008 (14)
C260.0250 (14)0.0340 (15)0.0363 (16)0.0002 (12)0.0039 (12)0.0041 (12)
C310.0291 (11)0.0246 (11)0.0258 (11)0.0054 (9)0.0006 (17)0.0009 (16)
C320.0319 (12)0.0258 (11)0.0330 (14)0.0042 (10)0.0030 (17)0.0040 (15)
C330.0331 (13)0.0391 (14)0.0435 (16)0.0106 (11)0.0098 (18)0.0087 (19)
C340.0568 (18)0.0333 (13)0.0370 (14)0.0204 (13)0.008 (2)0.0001 (19)
C350.0613 (19)0.0233 (12)0.0453 (16)0.0058 (12)0.013 (2)0.0031 (18)
C360.0414 (15)0.0259 (11)0.0440 (15)0.0001 (11)0.0104 (19)0.003 (2)
O1S0.133 (11)0.075 (6)0.125 (9)0.020 (6)0.079 (8)0.014 (6)
C1S0.067 (8)0.24 (2)0.081 (9)0.038 (11)0.020 (7)0.004 (12)
Geometric parameters (Å, º) top
Ru1—N12.011 (3)C4—C51.450 (4)
Ru1—N1i2.011 (3)C11—C161.393 (4)
Ru1—N2i2.051 (3)C11—C121.400 (4)
Ru1—N22.051 (3)C12—C131.382 (5)
Ru1—P12.4071 (5)C13—C141.383 (5)
Ru1—P1i2.4071 (5)C14—C151.372 (5)
P1—C211.817 (3)C15—C161.392 (4)
P1—C111.824 (3)C21—C221.395 (4)
P1—C311.834 (2)C21—C261.401 (4)
P2—F21.579 (2)C22—C231.397 (5)
P2—F41.585 (2)C23—C241.375 (5)
P2—F31.590 (2)C24—C251.378 (5)
P2—F51.594 (2)C25—C261.384 (4)
P2—F11.595 (3)C31—C321.385 (3)
P2—F61.609 (2)C31—C361.392 (3)
N1—C11.308 (4)C32—C331.396 (4)
N2—C41.141 (4)C33—C341.371 (4)
C1—C21.435 (4)C34—C351.382 (4)
C1—C1i1.457 (5)C35—C361.384 (4)
C2—C31.354 (5)O1S—C1S1.20 (2)
C3—C3i1.444 (7)
N1—Ru1—N1i77.63 (15)F5—P2—F690.01 (12)
N1—Ru1—N2i94.05 (10)F1—P2—F690.03 (14)
N1i—Ru1—N2i171.24 (11)C1—N1—Ru1117.2 (2)
N1—Ru1—N2171.24 (11)C4—N2—Ru1173.7 (3)
N1i—Ru1—N294.05 (10)N1—C1—C2126.4 (3)
N2i—Ru1—N294.39 (15)N1—C1—C1i113.99 (17)
N1—Ru1—P188.47 (8)C2—C1—C1i119.60 (17)
N1i—Ru1—P192.14 (8)C3—C2—C1118.4 (3)
N2i—Ru1—P190.32 (8)C2—C3—C3i121.9 (2)
N2—Ru1—P189.15 (8)N2—C4—C5179.6 (4)
N1—Ru1—P1i92.14 (8)C16—C11—C12118.8 (3)
N1i—Ru1—P1i88.47 (8)C16—C11—P1123.0 (2)
N2i—Ru1—P1i89.15 (8)C12—C11—P1117.7 (2)
N2—Ru1—P1i90.32 (8)C13—C12—C11120.7 (3)
P1—Ru1—P1i179.22 (5)C12—C13—C14119.8 (3)
C21—P1—C11107.55 (12)C15—C14—C13120.3 (3)
C21—P1—C31102.75 (15)C14—C15—C16120.5 (3)
C11—P1—C31100.23 (15)C15—C16—C11119.9 (3)
C21—P1—Ru1108.94 (10)C22—C21—C26119.2 (3)
C11—P1—Ru1116.22 (10)C22—C21—P1119.8 (2)
C31—P1—Ru1119.78 (8)C26—C21—P1120.2 (2)
F2—P2—F490.58 (13)C21—C22—C23119.8 (3)
F2—P2—F390.69 (12)C24—C23—C22120.3 (3)
F4—P2—F390.48 (13)C23—C24—C25120.1 (3)
F2—P2—F590.43 (12)C24—C25—C26120.7 (3)
F4—P2—F590.23 (13)C25—C26—C21119.8 (3)
F3—P2—F5178.67 (13)C32—C31—C36119.4 (2)
F2—P2—F1179.43 (17)C32—C31—P1122.69 (18)
F4—P2—F189.94 (15)C36—C31—P1117.87 (19)
F3—P2—F189.08 (13)C31—C32—C33119.9 (2)
F5—P2—F189.80 (14)C34—C33—C32120.4 (3)
F2—P2—F689.44 (13)C33—C34—C35119.8 (2)
F4—P2—F6179.76 (16)C34—C35—C36120.5 (3)
F3—P2—F689.28 (12)C35—C36—C31120.0 (3)
Symmetry code: (i) x, y, z.

Experimental details

Crystal data
Chemical formula[Ru(C2H3N)2(C6H6N2)(C18H15P)2](PF6)2·CH4O
Mr1135.83
Crystal system, space groupOrthorhombic, Aba2
Temperature (K)100
a, b, c (Å)19.0603 (5), 16.5960 (4), 15.4192 (3)
V3)4877.5 (2)
Z4
Radiation typeMo Kα
µ (mm1)0.54
Crystal size (mm)0.39 × 0.38 × 0.31
Data collection
DiffractometerNonius KappaCCD
diffractometer
Absorption correctionMulti-scan
(DENZO-SMN; Otwinowski & Minor, 1997)
Tmin, Tmax0.817, 0.851
No. of measured, independent and
observed [I > 2σ(I)] reflections
14495, 4778, 4410
Rint0.049
(sin θ/λ)max1)0.625
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.027, 0.073, 1.07
No. of reflections4778
No. of parameters325
No. of restraints1
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.43, 0.25
Absolute structureFlack (1983), 2205 Friedel pairs
Absolute structure parameter0.52 (3)

Computer programs: KappaCCD Server Software (Nonius, 1997), DENZO-SMN (Otwinowski & Minor, 1997), DENZO-SMN, SHELXTL (Sheldrick, 1997), SHELXTL.

Selected geometric parameters (Å, º) top
Ru1—N12.011 (3)Ru1—P1i2.4071 (5)
Ru1—N1i2.011 (3)C1—C21.435 (4)
Ru1—N2i2.051 (3)C1—C1i1.457 (5)
Ru1—N22.051 (3)C2—C31.354 (5)
Ru1—P12.4071 (5)C3—C3i1.444 (7)
N1—Ru1—N1i77.63 (15)P1—Ru1—P1i179.22 (5)
N1i—Ru1—N294.05 (10)
Symmetry code: (i) x, y, z.
 

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