Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270102001701/da1216sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270102001701/da1216Isup2.hkl |
CCDC reference: 184468
Data collection: CAD-4 EXPRESS (Enraf-Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).
[Ru(C6H16N2)(C2H5O)NO(NO2)2] | Dx = 1.740 Mg m−3 |
Mr = 384.37 | Cu Kα radiation, λ = 1.5418 Å |
Trigonal, P31 | Cell parameters from 25 reflections |
a = 7.930 (2) Å | θ = 10.1–21.6° |
c = 20.210 (9) Å | µ = 8.97 mm−1 |
V = 1100.6 (6) Å3 | T = 293 K |
Z = 3 | Prism, dark orange |
F(000) = 588 | 0.08 × 0.06 × 0.06 mm |
Enraf-Nonius CAD-4 diffractometer | 1431 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.045 |
Graphite monochromator | θmax = 69.8°, θmin = 6.5° |
non–profiled ω/2θ scans | h = 0→9 |
Absorption correction: ψ-scan (North et al., 1968) | k = −9→0 |
Tmin = 0.439, Tmax = 0.566 | l = 0→24 |
1593 measured reflections | 1 standard reflections every 30 min |
1439 independent reflections | intensity decay: 1% |
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)] = 0.035 | H-atom parameters constrained |
wR(F2) = 0.094 | w = 1/[σ2(Fo2) + (0.0392P)2 + 4.2825P] where P = (Fo2 + 2Fc2)/3 |
S = 1.15 | (Δ/σ)max < 0.001 |
1439 reflections | Δρmax = 0.87 e Å−3 |
207 parameters | Δρmin = −1.72 e Å−3 |
1 restraint | Absolute structure: Flack (1983) |
Primary atom site location: Patterson | Absolute structure parameter: 0.04 (2) |
Experimental. Spectroscopic analysis: IR (KBr disc, νN—O, cm-1): 1832; 1H NMR (CDCl3, δ, p.p.m.): 4.72 (q, 2H, CH2 in OEt), 3.02 (t, 3H, CH3 in OEt), 2.89 (s, 6H, CH3 in TMED), 2.79 (m, 4H, CH2 in TMED), 2.71 (s, 6H, CH3 in TMED). IR spectra were recorded on a Nicolet FTIR 510P. 1H NMR spectra were run on a 200 MHz Bruker AC200 instrument in a CDCl3 solution, using the solvent peak as the internal reference (δ 7.26 p.p.m.). |
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 | ||
Ru | 0.43700 (8) | 0.20021 (8) | 0.00000 (5) | 0.02372 (18) | |
N1 | 0.4983 (13) | 0.0822 (14) | −0.0608 (4) | 0.038 (2) | |
O1 | 0.5637 (17) | 0.0251 (18) | −0.1000 (5) | 0.071 (3) | |
N2 | 0.2107 (12) | −0.0682 (13) | 0.0478 (4) | 0.0286 (18) | |
C21 | 0.239 (2) | −0.0613 (17) | 0.1218 (5) | 0.048 (3) | |
H21A | 0.2213 | 0.0407 | 0.1402 | 0.03 (3)* | |
H21B | 0.3676 | −0.0363 | 0.1316 | 0.03 (3)* | |
H21C | 0.1448 | −0.1838 | 0.1408 | 0.05 (3)* | |
C22 | 0.2091 (18) | −0.2452 (15) | 0.0225 (6) | 0.044 (3) | |
H22A | 0.1139 | −0.3573 | 0.0464 | 0.3 (2)* | |
H22B | 0.3354 | −0.2315 | 0.0286 | 0.05 (4)* | |
H22C | 0.1769 | −0.2611 | −0.0237 | 0.02 (2)* | |
C3 | 0.0201 (13) | −0.0222 (15) | −0.0373 (5) | 0.036 (2) | |
H3A | 0.0240 | −0.1188 | −0.0657 | 0.03 (3)* | |
H3B | −0.1016 | −0.0244 | −0.0455 | 0.02 (2)* | |
N3 | 0.1868 (12) | 0.1751 (13) | −0.0540 (4) | 0.0307 (19) | |
C31 | 0.1358 (17) | 0.3233 (17) | −0.0339 (6) | 0.040 (3) | |
H31A | 0.2507 | 0.4497 | −0.0343 | 0.05 (3)* | |
H31B | 0.0817 | 0.2947 | 0.0099 | 0.06 (4)* | |
H31C | 0.0418 | 0.3218 | −0.0642 | 0.05 (4)* | |
C32 | 0.2190 (18) | 0.1934 (19) | −0.1263 (5) | 0.044 (3) | |
H32A | 0.1044 | 0.1780 | −0.1480 | 0.10 (6)* | |
H32B | 0.2460 | 0.0946 | −0.1415 | 0.03 (3)* | |
H32C | 0.3274 | 0.3195 | −0.1364 | 0.03 (3)* | |
C4 | 0.0276 (15) | −0.0732 (17) | 0.0336 (6) | 0.039 (2) | |
H4A | 0.0153 | 0.0185 | 0.0621 | 0.03 (3)* | |
H4B | −0.0806 | −0.2023 | 0.0427 | 0.02 (2)* | |
N4 | 0.6666 (16) | 0.2117 (15) | 0.0561 (5) | 0.041 (2) | |
O3 | 0.6836 (14) | 0.0656 (16) | 0.0570 (5) | 0.063 (3) | |
O4 | 0.7794 (14) | 0.3582 (17) | 0.0852 (6) | 0.067 (3) | |
N5 | 0.6303 (14) | 0.4645 (14) | −0.0460 (5) | 0.039 (2) | |
O5 | 0.7857 (15) | 0.4861 (16) | −0.0653 (7) | 0.073 (3) | |
O6 | 0.5938 (13) | 0.5947 (12) | −0.0521 (5) | 0.062 (2) | |
O2 | 0.3778 (10) | 0.3238 (10) | 0.0693 (3) | 0.0348 (15) | |
C5 | 0.4808 (17) | 0.5047 (16) | 0.1020 (6) | 0.046 (3) | |
H5A | 0.5187 | 0.6104 | 0.0706 | 0.01 (2)* | |
H5B | 0.5975 | 0.5179 | 0.1224 | 0.04 (3)* | |
C6 | 0.349 (2) | 0.5116 (18) | 0.1536 (6) | 0.050 (3) | |
H6A | 0.3143 | 0.4077 | 0.1847 | 0.08 (5)* | |
H6B | 0.2338 | 0.4972 | 0.1329 | 0.27 (19)* | |
H6C | 0.4154 | 0.6342 | 0.1763 | 0.07 (4)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Ru | 0.0176 (3) | 0.0227 (3) | 0.0271 (3) | 0.0073 (2) | 0.0013 (2) | −0.0003 (3) |
N1 | 0.031 (4) | 0.043 (5) | 0.040 (5) | 0.017 (4) | 0.002 (4) | −0.006 (4) |
O1 | 0.086 (7) | 0.101 (8) | 0.050 (6) | 0.066 (7) | 0.009 (5) | −0.022 (5) |
N2 | 0.020 (4) | 0.032 (4) | 0.036 (5) | 0.014 (4) | 0.002 (3) | 0.007 (4) |
C21 | 0.059 (7) | 0.041 (6) | 0.031 (6) | 0.014 (5) | 0.013 (5) | 0.011 (5) |
C22 | 0.057 (7) | 0.029 (5) | 0.047 (6) | 0.021 (5) | −0.002 (5) | −0.003 (5) |
C3 | 0.020 (4) | 0.032 (5) | 0.045 (6) | 0.005 (4) | −0.003 (4) | 0.003 (4) |
N3 | 0.022 (4) | 0.033 (4) | 0.030 (4) | 0.008 (3) | 0.003 (3) | 0.001 (3) |
C31 | 0.040 (6) | 0.039 (6) | 0.041 (6) | 0.020 (5) | −0.006 (5) | 0.000 (5) |
C32 | 0.049 (6) | 0.053 (7) | 0.033 (6) | 0.028 (6) | −0.006 (5) | 0.002 (5) |
C4 | 0.028 (5) | 0.033 (5) | 0.055 (7) | 0.013 (4) | 0.003 (5) | 0.006 (5) |
N4 | 0.042 (5) | 0.039 (5) | 0.045 (5) | 0.024 (5) | −0.008 (4) | −0.005 (4) |
O3 | 0.059 (6) | 0.080 (7) | 0.069 (6) | 0.047 (6) | −0.009 (5) | 0.003 (5) |
O4 | 0.040 (5) | 0.076 (7) | 0.084 (8) | 0.027 (5) | −0.022 (5) | −0.016 (6) |
N5 | 0.031 (5) | 0.038 (5) | 0.033 (5) | 0.007 (4) | −0.004 (4) | −0.001 (4) |
O5 | 0.036 (5) | 0.060 (6) | 0.109 (9) | 0.014 (4) | 0.026 (6) | 0.020 (6) |
O6 | 0.060 (5) | 0.035 (4) | 0.080 (6) | 0.015 (4) | 0.018 (5) | 0.022 (4) |
O2 | 0.036 (4) | 0.034 (4) | 0.032 (4) | 0.015 (3) | 0.003 (3) | −0.004 (3) |
C5 | 0.045 (6) | 0.035 (6) | 0.051 (7) | 0.013 (5) | −0.001 (5) | −0.019 (5) |
C6 | 0.070 (8) | 0.047 (6) | 0.041 (6) | 0.036 (6) | −0.002 (5) | −0.008 (5) |
Ru—N1 | 1.754 (9) | C21—H21B | 0.96 |
Ru—O2 | 1.898 (7) | C21—H21C | 0.96 |
Ru—N5 | 2.10 (1) | C22—H22A | 0.96 |
Ru—N4 | 2.11 (1) | C22—H22B | 0.96 |
Ru—N3 | 2.185 (9) | C22—H22C | 0.96 |
Ru—N2 | 2.205 (9) | C3—H3A | 0.97 |
N1—O1 | 1.16 (1) | C3—H3B | 0.97 |
N2—C4 | 1.46 (1) | C31—H31A | 0.96 |
N2—C22 | 1.49 (1) | C31—H31B | 0.96 |
N2—C21 | 1.51 (1) | C31—H31C | 0.96 |
C3—N3 | 1.50 (1) | C32—H32A | 0.96 |
C3—C4 | 1.50 (2) | C32—H32B | 0.96 |
N3—C32 | 1.48 (1) | C32—H32C | 0.96 |
N3—C31 | 1.48 (2) | C4—H4A | 0.97 |
N4—O4 | 1.21 (1) | C4—H4B | 0.97 |
N4—O3 | 1.23 (1) | C5—H5A | 0.97 |
N5—O6 | 1.21 (1) | C5—H5B | 0.97 |
N5—O5 | 1.22 (1) | C6—H6A | 0.96 |
O2—C5 | 1.41 (1) | C6—H6B | 0.96 |
C5—C6 | 1.50 (2) | C6—H6C | 0.96 |
C21—H21A | 0.96 | ||
N1—Ru—O2 | 176.8 (4) | C5—O2—Ru | 134.7 (7) |
N1—Ru—N5 | 87.9 (4) | O2—C5—C6 | 107.7 (9) |
O2—Ru—N5 | 93.3 (4) | H21A—C21—H21B | 109.5 (12) |
N1—Ru—N4 | 86.3 (4) | H21A—C21—H21C | 109.5 (13) |
O2—Ru—N4 | 90.7 (4) | H21B—C21—H21C | 109.5 (12) |
N5—Ru—N4 | 90.6 (4) | H22A—C22—H22B | 109.5 (12) |
N1—Ru—N3 | 94.7 (4) | H22A—C22—H22C | 109.5 (12) |
O2—Ru—N3 | 88.2 (3) | H22B—C22—H22C | 109.5 (13) |
N5—Ru—N3 | 92.7 (3) | H3A—C3—H3B | 108.0 (10) |
N4—Ru—N3 | 176.6 (4) | H3A—C3—C4 | 109.4 (10) |
N1—Ru—N2 | 95.8 (4) | H3B—C3—C4 | 109.4 (10) |
O2—Ru—N2 | 83.3 (3) | N3—C3—H3A | 109.4 (10) |
N5—Ru—N2 | 174.0 (4) | N3—C3—H3B | 109.3 (10) |
N4—Ru—N2 | 94.3 (4) | H31A—C31—H31B | 109.5 (12) |
N3—Ru—N2 | 82.4 (3) | H31A—C31—H31C | 109.5 (12) |
O1—N1—Ru | 171 (1) | H31B—C31—H31C | 109.5 (12) |
C4—N2—C22 | 111.6 (9) | H32A—C32—H32B | 109.5 (12) |
C4—N2—C21 | 108.8 (9) | H32A—C32—H32C | 109.5 (12) |
C22—N2—C21 | 107.8 (9) | H32B—C32—H32C | 109.5 (12) |
C4—N2—Ru | 105.0 (6) | N2—C4—H4A | 109.5 (10) |
C22—N2—Ru | 112.3 (7) | N2—C4—H4B | 109.5 (10) |
C21—N2—Ru | 111.4 (7) | C3—C4—H4A | 109.5 (10) |
N3—C3—C4 | 111.4 (8) | C3—C4—H4B | 109.5 (11) |
C32—N3—C31 | 107.3 (9) | H4A—C4—H4B | 108.1 (11) |
C32—N3—C3 | 110.2 (9) | O2—C5—H5A | 110.2 (11) |
C31—N3—C3 | 108.6 (8) | O2—C5—H5B | 110.2 (10) |
C32—N3—Ru | 112.4 (7) | H5A—C5—H5B | 108.5 (12) |
C31—N3—Ru | 112.8 (7) | H5A—C5—C6 | 110.2 (11) |
C3—N3—Ru | 105.7 (6) | H5B—C5—C6 | 110.2 (12) |
N2—C4—C3 | 110.7 (9) | C5—C6—H6A | 109.5 (12) |
O4—N4—O3 | 121 (1) | C5—C6—H6B | 109.5 (11) |
O4—N4—Ru | 120.8 (8) | C5—C6—H6C | 109.5 (12) |
O3—N4—Ru | 117.7 (8) | H6A—C6—H6B | 109.5 (13) |
O6—N5—O5 | 120 (1) | H6A—C6—H6C | 109.5 (12) |
O6—N5—Ru | 122.0 (8) | H6B—C6—H6C | 109.5 (13) |
O5—N5—Ru | 117.7 (9) |