Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270100007654/qa0305sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270100007654/qa0305Isup2.hkl |
CCDC reference: 147684
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.
[Ru(C2H3N)2(C6H6N2)(C18H15P)2](PF6)2·CH4O | F(000) = 2304 |
Mr = 1135.83 | Dx = 1.547 Mg m−3 |
Orthorhombic, Aba2 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: A 2 -2ab | Cell parameters from 14495 reflections |
a = 19.0603 (5) Å | θ = 4.2–23.7° |
b = 16.5960 (4) Å | µ = 0.54 mm−1 |
c = 15.4192 (3) Å | T = 100 K |
V = 4877.5 (2) Å3 | Block cut from needle, purple |
Z = 4 | 0.39 × 0.38 × 0.31 mm |
Nonius KappaCCD diffractometer | 4778 independent reflections |
Radiation source: fine-focus sealed tube | 4410 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.049 |
ϕ and ω scans with κ offsets | θmax = 26.4°, θmin = 4.2° |
Absorption correction: multi-scan (DENZO-SMN; Otwinowski & Minor, 1997) | h = −23→23 |
Tmin = 0.817, Tmax = 0.851 | k = −20→20 |
14495 measured reflections | l = −19→19 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.027 | H-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 reflections | Δρmax = 0.43 e Å−3 |
325 parameters | Δρmin = −0.25 e Å−3 |
1 restraint | Absolute structure: Flack (1983), 2205 Friedel pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.52 (3) |
[Ru(C2H3N)2(C6H6N2)(C18H15P)2](PF6)2·CH4O | V = 4877.5 (2) Å3 |
Mr = 1135.83 | Z = 4 |
Orthorhombic, Aba2 | Mo Kα radiation |
a = 19.0603 (5) Å | µ = 0.54 mm−1 |
b = 16.5960 (4) Å | T = 100 K |
c = 15.4192 (3) Å | 0.39 × 0.38 × 0.31 mm |
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 = 0.851 | Rint = 0.049 |
14495 measured reflections |
R[F2 > 2σ(F2)] = 0.027 | H-atom parameters constrained |
wR(F2) = 0.073 | Δρmax = 0.43 e Å−3 |
S = 1.07 | Δρmin = −0.25 e Å−3 |
4778 reflections | Absolute structure: Flack (1983), 2205 Friedel pairs |
325 parameters | Absolute structure parameter: 0.52 (3) |
1 restraint |
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. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
Ru1 | 0.0000 | 0.0000 | 0.37103 (3) | 0.02033 (7) | |
P1 | 0.03583 (3) | 0.13908 (3) | 0.37209 (6) | 0.02250 (12) | |
P2 | 0.28798 (4) | −0.06658 (5) | 0.32065 (6) | 0.03187 (17) | |
F1 | 0.25220 (11) | 0.00277 (10) | 0.3770 (3) | 0.0539 (5) | |
F2 | 0.32288 (12) | −0.13505 (13) | 0.26411 (14) | 0.0568 (6) | |
F3 | 0.31591 (12) | 0.00030 (11) | 0.25543 (14) | 0.0468 (5) | |
F4 | 0.35729 (10) | −0.05864 (14) | 0.3768 (2) | 0.0636 (6) | |
F5 | 0.25840 (11) | −0.13238 (12) | 0.38648 (15) | 0.0515 (6) | |
F6 | 0.21771 (10) | −0.07433 (14) | 0.26339 (16) | 0.0563 (6) | |
N1 | −0.06236 (13) | 0.02523 (16) | 0.26943 (17) | 0.0235 (5) | |
H1A | −0.1056 | 0.0425 | 0.2768 | 0.028* | |
N2 | 0.07600 (14) | −0.02450 (17) | 0.46141 (17) | 0.0262 (5) | |
C1 | −0.03598 (14) | 0.01483 (15) | 0.19195 (18) | 0.0244 (6) | |
C2 | −0.07065 (16) | 0.03035 (18) | 0.11102 (19) | 0.0300 (6) | |
H2A | −0.1175 | 0.0499 | 0.1098 | 0.036* | |
C3 | −0.03505 (19) | 0.0165 (2) | 0.0366 (2) | 0.0359 (8) | |
H3 | −0.0568 | 0.0288 | −0.0173 | 0.043* | |
C4 | 0.12267 (15) | −0.03700 (19) | 0.50579 (19) | 0.0296 (6) | |
C5 | 0.18201 (19) | −0.0523 (3) | 0.5623 (2) | 0.0549 (10) | |
H5A | 0.2243 | −0.0604 | 0.5271 | 0.082* | |
H5B | 0.1729 | −0.1006 | 0.5970 | 0.082* | |
H5C | 0.1889 | −0.0060 | 0.6009 | 0.082* | |
C11 | 0.08813 (16) | 0.17132 (19) | 0.4648 (2) | 0.0265 (6) | |
C12 | 0.06463 (16) | 0.14962 (18) | 0.54766 (19) | 0.0301 (6) | |
H12A | 0.0261 | 0.1137 | 0.5535 | 0.036* | |
C13 | 0.0969 (2) | 0.1799 (2) | 0.6210 (2) | 0.0355 (8) | |
H13A | 0.0807 | 0.1646 | 0.6769 | 0.043* | |
C14 | 0.15288 (18) | 0.2324 (2) | 0.6127 (2) | 0.0399 (8) | |
H14A | 0.1749 | 0.2536 | 0.6631 | 0.048* | |
C15 | 0.17679 (18) | 0.2539 (2) | 0.5321 (2) | 0.0414 (8) | |
H15A | 0.2156 | 0.2896 | 0.5270 | 0.050* | |
C16 | 0.14470 (17) | 0.2240 (2) | 0.4577 (2) | 0.0367 (7) | |
H16A | 0.1614 | 0.2395 | 0.4020 | 0.044* | |
C21 | 0.08659 (17) | 0.15953 (18) | 0.2748 (2) | 0.0265 (6) | |
C22 | 0.05346 (16) | 0.19109 (18) | 0.2017 (2) | 0.0317 (6) | |
H22A | 0.0061 | 0.2088 | 0.2051 | 0.038* | |
C23 | 0.0901 (2) | 0.1965 (2) | 0.1234 (2) | 0.0398 (8) | |
H23A | 0.0676 | 0.2181 | 0.0736 | 0.048* | |
C24 | 0.15847 (19) | 0.1707 (2) | 0.1181 (2) | 0.0434 (8) | |
H24A | 0.1832 | 0.1748 | 0.0648 | 0.052* | |
C25 | 0.19127 (16) | 0.13897 (19) | 0.1900 (2) | 0.0380 (7) | |
H25A | 0.2386 | 0.1214 | 0.1859 | 0.046* | |
C26 | 0.15598 (15) | 0.13236 (18) | 0.2681 (2) | 0.0317 (6) | |
H26A | 0.1788 | 0.1095 | 0.3171 | 0.038* | |
C31 | −0.03068 (12) | 0.21894 (13) | 0.3703 (3) | 0.0265 (5) | |
C32 | −0.10196 (13) | 0.20295 (15) | 0.3668 (3) | 0.0302 (5) | |
H32A | −0.1181 | 0.1488 | 0.3647 | 0.036* | |
C33 | −0.14995 (15) | 0.26648 (17) | 0.3665 (3) | 0.0386 (6) | |
H33A | −0.1988 | 0.2554 | 0.3643 | 0.046* | |
C34 | −0.12703 (16) | 0.34472 (16) | 0.3692 (3) | 0.0424 (7) | |
H34A | −0.1599 | 0.3877 | 0.3699 | 0.051* | |
C35 | −0.05592 (17) | 0.36081 (16) | 0.3710 (3) | 0.0433 (7) | |
H35A | −0.0400 | 0.4151 | 0.3711 | 0.052* | |
C36 | −0.00769 (14) | 0.29849 (15) | 0.3727 (4) | 0.0371 (6) | |
H36A | 0.0411 | 0.3100 | 0.3755 | 0.045* | |
O1S | −0.0285 (7) | 0.0146 (6) | 0.6929 (8) | 0.111 (4) | 0.50 |
H1S | −0.0517 | −0.0013 | 0.7360 | 0.166* | 0.50 |
C1S | −0.0408 (7) | 0.0844 (14) | 0.6798 (10) | 0.131 (7) | 0.50 |
H1S1 | −0.0002 | 0.1170 | 0.6969 | 0.196* | 0.50 |
H1S2 | −0.0819 | 0.1007 | 0.7139 | 0.196* | 0.50 |
H1S3 | −0.0504 | 0.0925 | 0.6180 | 0.196* | 0.50 |
U11 | U22 | U33 | U12 | U13 | U23 | |
Ru1 | 0.01824 (12) | 0.02177 (12) | 0.02098 (13) | 0.00139 (10) | 0.000 | 0.000 |
P1 | 0.0214 (3) | 0.0218 (3) | 0.0243 (3) | 0.0009 (2) | −0.0009 (4) | 0.0003 (4) |
P2 | 0.0266 (3) | 0.0326 (4) | 0.0364 (4) | 0.0020 (3) | −0.0015 (3) | −0.0018 (3) |
F1 | 0.0688 (12) | 0.0426 (9) | 0.0504 (13) | 0.0097 (9) | 0.0181 (17) | −0.0006 (11) |
F2 | 0.0632 (14) | 0.0508 (12) | 0.0564 (13) | 0.0195 (11) | 0.0022 (11) | −0.0120 (10) |
F3 | 0.0545 (13) | 0.0478 (12) | 0.0382 (11) | −0.0117 (9) | 0.0053 (9) | −0.0003 (8) |
F4 | 0.0463 (11) | 0.0832 (15) | 0.0611 (13) | −0.0068 (10) | −0.0244 (14) | −0.0054 (15) |
F5 | 0.0588 (12) | 0.0429 (10) | 0.0528 (15) | −0.0037 (9) | 0.0012 (10) | 0.0084 (9) |
F6 | 0.0346 (11) | 0.0662 (14) | 0.0681 (14) | −0.0029 (10) | −0.0187 (10) | 0.0074 (11) |
N1 | 0.0193 (12) | 0.0218 (11) | 0.0294 (13) | 0.0033 (10) | 0.0009 (10) | 0.0007 (10) |
N2 | 0.0305 (14) | 0.0247 (12) | 0.0234 (13) | 0.0021 (11) | 0.0006 (11) | −0.0023 (10) |
C1 | 0.0244 (15) | 0.0246 (13) | 0.0243 (14) | 0.0014 (10) | 0.0002 (11) | −0.0009 (10) |
C2 | 0.0282 (14) | 0.0326 (15) | 0.0292 (15) | 0.0038 (12) | −0.0057 (12) | 0.0012 (12) |
C3 | 0.040 (2) | 0.0457 (18) | 0.0217 (16) | 0.0048 (15) | −0.0002 (14) | 0.0029 (14) |
C4 | 0.0288 (15) | 0.0373 (16) | 0.0228 (14) | 0.0061 (12) | −0.0018 (12) | −0.0029 (12) |
C5 | 0.0372 (19) | 0.093 (3) | 0.0344 (19) | 0.0191 (19) | −0.0145 (15) | −0.0105 (19) |
C11 | 0.0235 (15) | 0.0275 (14) | 0.0285 (15) | 0.0032 (12) | −0.0042 (13) | −0.0013 (13) |
C12 | 0.0290 (14) | 0.0305 (14) | 0.0308 (15) | 0.0018 (12) | 0.0008 (12) | −0.0003 (13) |
C13 | 0.041 (2) | 0.0379 (17) | 0.0279 (16) | 0.0058 (14) | −0.0019 (14) | −0.0021 (15) |
C14 | 0.0407 (17) | 0.043 (2) | 0.0357 (18) | 0.0026 (14) | −0.0143 (14) | −0.0064 (16) |
C15 | 0.0386 (17) | 0.0447 (18) | 0.0407 (18) | −0.0113 (14) | −0.0111 (14) | −0.0014 (14) |
C16 | 0.0343 (16) | 0.0402 (17) | 0.0357 (16) | −0.0075 (14) | −0.0067 (13) | 0.0019 (13) |
C21 | 0.0272 (15) | 0.0224 (14) | 0.0299 (16) | −0.0016 (12) | 0.0009 (13) | 0.0009 (12) |
C22 | 0.0309 (15) | 0.0328 (15) | 0.0313 (15) | −0.0039 (13) | −0.0030 (12) | 0.0012 (13) |
C23 | 0.048 (2) | 0.049 (2) | 0.0224 (15) | −0.0045 (17) | 0.0007 (15) | 0.0072 (15) |
C24 | 0.046 (2) | 0.048 (2) | 0.0354 (17) | −0.0095 (16) | 0.0128 (15) | −0.0003 (16) |
C25 | 0.0305 (15) | 0.0417 (17) | 0.0418 (18) | 0.0009 (13) | 0.0115 (13) | 0.0008 (14) |
C26 | 0.0250 (14) | 0.0340 (15) | 0.0363 (16) | −0.0002 (12) | 0.0039 (12) | 0.0041 (12) |
C31 | 0.0291 (11) | 0.0246 (11) | 0.0258 (11) | 0.0054 (9) | 0.0006 (17) | −0.0009 (16) |
C32 | 0.0319 (12) | 0.0258 (11) | 0.0330 (14) | 0.0042 (10) | 0.0030 (17) | 0.0040 (15) |
C33 | 0.0331 (13) | 0.0391 (14) | 0.0435 (16) | 0.0106 (11) | 0.0098 (18) | 0.0087 (19) |
C34 | 0.0568 (18) | 0.0333 (13) | 0.0370 (14) | 0.0204 (13) | 0.008 (2) | −0.0001 (19) |
C35 | 0.0613 (19) | 0.0233 (12) | 0.0453 (16) | 0.0058 (12) | −0.013 (2) | −0.0031 (18) |
C36 | 0.0414 (15) | 0.0259 (11) | 0.0440 (15) | 0.0001 (11) | −0.0104 (19) | −0.003 (2) |
O1S | 0.133 (11) | 0.075 (6) | 0.125 (9) | 0.020 (6) | 0.079 (8) | 0.014 (6) |
C1S | 0.067 (8) | 0.24 (2) | 0.081 (9) | −0.038 (11) | 0.020 (7) | −0.004 (12) |
Ru1—N1 | 2.011 (3) | C4—C5 | 1.450 (4) |
Ru1—N1i | 2.011 (3) | C11—C16 | 1.393 (4) |
Ru1—N2i | 2.051 (3) | C11—C12 | 1.400 (4) |
Ru1—N2 | 2.051 (3) | C12—C13 | 1.382 (5) |
Ru1—P1 | 2.4071 (5) | C13—C14 | 1.383 (5) |
Ru1—P1i | 2.4071 (5) | C14—C15 | 1.372 (5) |
P1—C21 | 1.817 (3) | C15—C16 | 1.392 (4) |
P1—C11 | 1.824 (3) | C21—C22 | 1.395 (4) |
P1—C31 | 1.834 (2) | C21—C26 | 1.401 (4) |
P2—F2 | 1.579 (2) | C22—C23 | 1.397 (5) |
P2—F4 | 1.585 (2) | C23—C24 | 1.375 (5) |
P2—F3 | 1.590 (2) | C24—C25 | 1.378 (5) |
P2—F5 | 1.594 (2) | C25—C26 | 1.384 (4) |
P2—F1 | 1.595 (3) | C31—C32 | 1.385 (3) |
P2—F6 | 1.609 (2) | C31—C36 | 1.392 (3) |
N1—C1 | 1.308 (4) | C32—C33 | 1.396 (4) |
N2—C4 | 1.141 (4) | C33—C34 | 1.371 (4) |
C1—C2 | 1.435 (4) | C34—C35 | 1.382 (4) |
C1—C1i | 1.457 (5) | C35—C36 | 1.384 (4) |
C2—C3 | 1.354 (5) | O1S—C1S | 1.20 (2) |
C3—C3i | 1.444 (7) | ||
N1—Ru1—N1i | 77.63 (15) | F5—P2—F6 | 90.01 (12) |
N1—Ru1—N2i | 94.05 (10) | F1—P2—F6 | 90.03 (14) |
N1i—Ru1—N2i | 171.24 (11) | C1—N1—Ru1 | 117.2 (2) |
N1—Ru1—N2 | 171.24 (11) | C4—N2—Ru1 | 173.7 (3) |
N1i—Ru1—N2 | 94.05 (10) | N1—C1—C2 | 126.4 (3) |
N2i—Ru1—N2 | 94.39 (15) | N1—C1—C1i | 113.99 (17) |
N1—Ru1—P1 | 88.47 (8) | C2—C1—C1i | 119.60 (17) |
N1i—Ru1—P1 | 92.14 (8) | C3—C2—C1 | 118.4 (3) |
N2i—Ru1—P1 | 90.32 (8) | C2—C3—C3i | 121.9 (2) |
N2—Ru1—P1 | 89.15 (8) | N2—C4—C5 | 179.6 (4) |
N1—Ru1—P1i | 92.14 (8) | C16—C11—C12 | 118.8 (3) |
N1i—Ru1—P1i | 88.47 (8) | C16—C11—P1 | 123.0 (2) |
N2i—Ru1—P1i | 89.15 (8) | C12—C11—P1 | 117.7 (2) |
N2—Ru1—P1i | 90.32 (8) | C13—C12—C11 | 120.7 (3) |
P1—Ru1—P1i | 179.22 (5) | C12—C13—C14 | 119.8 (3) |
C21—P1—C11 | 107.55 (12) | C15—C14—C13 | 120.3 (3) |
C21—P1—C31 | 102.75 (15) | C14—C15—C16 | 120.5 (3) |
C11—P1—C31 | 100.23 (15) | C15—C16—C11 | 119.9 (3) |
C21—P1—Ru1 | 108.94 (10) | C22—C21—C26 | 119.2 (3) |
C11—P1—Ru1 | 116.22 (10) | C22—C21—P1 | 119.8 (2) |
C31—P1—Ru1 | 119.78 (8) | C26—C21—P1 | 120.2 (2) |
F2—P2—F4 | 90.58 (13) | C21—C22—C23 | 119.8 (3) |
F2—P2—F3 | 90.69 (12) | C24—C23—C22 | 120.3 (3) |
F4—P2—F3 | 90.48 (13) | C23—C24—C25 | 120.1 (3) |
F2—P2—F5 | 90.43 (12) | C24—C25—C26 | 120.7 (3) |
F4—P2—F5 | 90.23 (13) | C25—C26—C21 | 119.8 (3) |
F3—P2—F5 | 178.67 (13) | C32—C31—C36 | 119.4 (2) |
F2—P2—F1 | 179.43 (17) | C32—C31—P1 | 122.69 (18) |
F4—P2—F1 | 89.94 (15) | C36—C31—P1 | 117.87 (19) |
F3—P2—F1 | 89.08 (13) | C31—C32—C33 | 119.9 (2) |
F5—P2—F1 | 89.80 (14) | C34—C33—C32 | 120.4 (3) |
F2—P2—F6 | 89.44 (13) | C33—C34—C35 | 119.8 (2) |
F4—P2—F6 | 179.76 (16) | C34—C35—C36 | 120.5 (3) |
F3—P2—F6 | 89.28 (12) | C35—C36—C31 | 120.0 (3) |
Symmetry code: (i) −x, −y, z. |
Experimental details
Crystal data | |
Chemical formula | [Ru(C2H3N)2(C6H6N2)(C18H15P)2](PF6)2·CH4O |
Mr | 1135.83 |
Crystal system, space group | Orthorhombic, Aba2 |
Temperature (K) | 100 |
a, b, c (Å) | 19.0603 (5), 16.5960 (4), 15.4192 (3) |
V (Å3) | 4877.5 (2) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.54 |
Crystal size (mm) | 0.39 × 0.38 × 0.31 |
Data collection | |
Diffractometer | Nonius KappaCCD diffractometer |
Absorption correction | Multi-scan (DENZO-SMN; Otwinowski & Minor, 1997) |
Tmin, Tmax | 0.817, 0.851 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 14495, 4778, 4410 |
Rint | 0.049 |
(sin θ/λ)max (Å−1) | 0.625 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.027, 0.073, 1.07 |
No. of reflections | 4778 |
No. of parameters | 325 |
No. of restraints | 1 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.43, −0.25 |
Absolute structure | Flack (1983), 2205 Friedel pairs |
Absolute structure parameter | 0.52 (3) |
Computer programs: KappaCCD Server Software (Nonius, 1997), DENZO-SMN (Otwinowski & Minor, 1997), DENZO-SMN, SHELXTL (Sheldrick, 1997), SHELXTL.
Ru1—N1 | 2.011 (3) | Ru1—P1i | 2.4071 (5) |
Ru1—N1i | 2.011 (3) | C1—C2 | 1.435 (4) |
Ru1—N2i | 2.051 (3) | C1—C1i | 1.457 (5) |
Ru1—N2 | 2.051 (3) | C2—C3 | 1.354 (5) |
Ru1—P1 | 2.4071 (5) | C3—C3i | 1.444 (7) |
N1—Ru1—N1i | 77.63 (15) | P1—Ru1—P1i | 179.22 (5) |
N1i—Ru1—N2 | 94.05 (10) |
Symmetry code: (i) −x, −y, z. |
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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.