metal-organic compounds
(η4-Bicyclo[2.2.1]hepta-2,5-diene)bis(η2-3,5-di-tert-butyl-1,2,4-diazaphospholido)ruthenium
aInstitute of Organic Chemistry and College of Chemical and Materials Science, Shanxi Normal University, Gongyuan Street 1, Linfen, Shanxi Province 041004, People's Republic of China
*Correspondence e-mail: wjzheng@sxnu.edu.cn, wjzheng_sxnu@qq.com
In the title compound, [Ru(C10H18N2P)2(C7H8)], the two 1,2,4-diazaphospholide (dp) ligands are coordinated to the RuII ion in an almost perfect η2-geometry, with Ru—N bond lengths in the range 2.071 (3)–2.135 (3) Å. The N—Ru—N angles within each η2-1,2,4-diazaphospholide ligand are similar, with values of 37.10 (11) and 37.44 (11)°, and hence the coodination geometry around the RuII ion is highly distorted from the expected octahedral geometry. One of the tert-butyl groups was refined as disordered over two sets of sites, with a ratio of occupancies of 0.719 (6):0.281 (6).
Keywords: crystal structure; ruthenium; 1,2,4-diazaphospholide.
CCDC reference: 660752
Structure description
The molecular structure of the title compound which incorporates a bicyclo[2.2.1]hepta-2,5-diene (NBD) ligand, [(η4-NBD)Ru(η2-3,5-tBu2dp)2], is illustrated in Fig. 1. The two 1,2,4-diazaphospholide (dp) ligands are coordinated to the ruthenium(II) atom with nearly perfect η2 geometry, with Ru—N bond lengths ranging from 2.071 (3) to 2.135 (3) Å. The N—Ru—N angles within each η2-1,2,4-diazaphospholide ligand are 37.10 (11) and 37.44 (11)°. The N—N bonds of the dp ligands are oriented with respect to the RuII so as to suggest σ-donation of the in-plane nitrogen atom lone pairs to the metal atom while the coordinating bicyclo[2.2.1]hepta-2,5-diene ligand is in a π-bonding mode with η4-coordination. This may be evidenced by the C=C bond lengths [C21=C22 1.395 (5); C26=C27 1.400 (5) Å] and Ru—C bonds [Ru1—C21 2.124 (4); Ru1—C22 2.133 (3) Å]. The bond angles (N1/N2-centroid)—Ru—(C26/C27-centroid) and (N3/N4-centroid)—Ru—(C21/C22-centroid) are 76.6 and 80.0°, respectively, suggesting a psuedo-tetrahedral arrangement of the ligands around RuII, although the coordination is highly distorted from the expected octahedral arrangement.
Synthesis and crystallization
All manipulations were carried out using standard Schlenk techniques in an N2 filled glovebox. Solvents were dried over and distilled from Na/K alloy prior to use.
To a mixture of [(η4-NBD)RuCl2] (Albers et al., 1989) (0.53 g, 2.0 mmol) and K[3,5-tBu2dp] (Zheng et al., 2006) (1.04 g, 4.4 mmol) was added 30 ml tetrahydrofuran via a syringe. After the solution had been stirred for 48 h, the volatile components were removed in high vacuum. The resulting residue was extracted with ether (3 × 10 ml). The solvent was reduced to about 10 ml and then the solution was kept at 253 K to give the title compound as deep-red crystals (0.88 g, 75%). M.p. 453 K (dep.). 1H NMR (C6D6, 296 K): δ = 1.15 (d, 18 H, CH3), 1.65 (d, 18 H, CH3), 1.19 (d, 2 H, CH2), 3.39 (d, 2 H, CH), 3.62 (t, 2 H, = CH), 4.83 (t, 2 H, = CH) p.p.m.; 13C{1H} NMR (C6D6, 296 K): δ = 31.80 (d, 3JCP = 6.25 Hz, CH3), 33.94 (d, 3JCP = 301.25 Hz, CH3), 50.92 (s, CH), 58.63 (s, CH2), 59.49, 60.26 (s, = CH), 181.81 (d, 2JCP = 62.13 CCH3), 185.24 (d, 1JCP = 63.50 Hz, PCN) p.p.m.; 31P{1H} NMR (C6D6, 296 K): δ = 67.79 (s), 114.75 (s) p.p.m.; MS(EI) m/z (%): 588 ([M+], 100); IR (KBr, Nujol mull, cm−1): 1463(s), 1377(s), 1291(m), 1086(w), 779(w), 718(m); Analysis calculated for C27H44RuP2N4: C 55.18; H 7.55; N 9.53. Found: C 55.31; H, 7.61; N, 9.67.
Refinement
Crystal data, data collection and structure . One of the tert-butyl groups (C18/C19/C20) was refined as disordered over two sets of sites with an occupancy ratio of 0.719 (6):0.281 (6).
details are summarized in Table 1Structural data
CCDC reference: 660752
10.1107/S2414314616001103/lh4001sup1.cif
contains datablock I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S2414314616001103/lh4001Isup2.hkl
All manipulations were carried out using standard Schlenk techniques in an N2 filled glovebox. Solvents were dried over and distilled from Na/K alloy prior to use.
To a mixture of [(η4-NBD)RuCl2] (Albers et al., 1989) (0.53 g, 2.0 mmol) and K[3,5 − tBu2dp] (Zheng et al., 2006) (1.04 g, 4.4 mmol) was added 30 ml tetrahydrofuran via a syringe. After the solution had been stirred for 48 h, the volatile components were removed in high vacuum. The resulting residue was extracted with ether (3 × 10 ml). The solvent was reduced to about 10 ml and then the solution was kept at 253 K to give the title compound as deep-red crystals (0.88 g, 75%). M.p. 453 K (dep.). 1H NMR (C6D6, 296 K): δ = 1.15 (d, 18 H, CH3), 1.65 (d, 18 H, CH3), 1.19 (d, 2 H, CH2), 3.39 (d, 2 H, CH), 3.62 (t, 2 H, = CH), 4.83 (t, 2 H, = CH) p.p.m.; 13C{1H} NMR (C6D6, 296 K): δ = 31.80 (d, 3JCP = 6.25 Hz, CH3), 33.94 (d, 3JCP = 301.25 Hz, CH3), 50.92 (s, CH), 58.63 (s, CH2), 59.49, 60.26 (s, = CH), 181.81 (d, 2JCP = 62.13 CCH3), 185.24 (d, 1JCP = 63.50 Hz, PCN) p.p.m.; 31P{1H} NMR (C6D6, 296 K): δ = 67.79 (s), 114.75 (s) p.p.m.; MS(EI) m/z (%): 588 ([M+], 100); IR (KBr, Nujol mull, cm−1): 1463(s), 1377(s), 1291(m), 1086(w), 779(w), 718(m); Analysis calculated for C27H44RuP2N4: C 55.18; H 7.55; N 9.53. Found: C 55.31; H, 7.61; N, 9.67.
Crystal data, data collection and structure
details are summarized in Table 1. One of the tert-butyl groups (C18/C19/C20) was refined as disordered over two sets of sites with an occupancy ratio of 0.719 (6):0.281 (6).The molecular structure of the title compound which incorporates a bicyclo[2.2.1]hepta-2,5-diene (NBD) ligand, [(η4-NBD)Ru(η2-3,5 − tBu2dp)2], is illustrated in Fig. 1. The two 1,2,4-diazaphospholide (dp) ligands are coordinated to the ruthenium(II) atom with nearly perfect η2 geometry, with Ru—N bond lengths ranging from 2.071 (3) to 2.135 (3) Å. The N—Ru—N angles within each η2-1,2,4-diazaphospholide ligand are 37.10 (11) and 37.44 (11)°. The N—N bonds of the dp ligands are oriented with respect to the RuII so as to suggest σ-donation of the in-plane nitrogen atom lone pairs to the metal atom while the coordinating bicyclo[2.2.1]hepta-2,5-diene ligand is in a π-bonding mode with η4-coordination. This may be evidenced by the C═C bond lengths [C21═C22 1.395 (5); C26═C27 1.400 (5) Å] and Ru—C bonds [Ru1—C21 2.124 (4); Ru1—C22 2.133 (3) Å]. The bond angles (N1/N2-centroid)—Ru—(C26/C27-centroid) and (N3/N4-centroid)—Ru—(C21/C22-centroid) are 76.6 and 80.0°, respectively, suggesting a psuedo-tetrahedral arrangement of the ligands around RuII, although the coordination is highly distorted from the expected octahedral arrangement.
Data collection: APEX2 (Bruker, 2009); cell
SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: publCIF (Westrip, 2010).Fig. 1. The molecular structure of the title compound. Displacement ellipsoids are drawn at the 30% probability level. H atoms and the minor disorder component have been omitted for clarity. |
[Ru(C10H18N2P)2(C7H8)] | Z = 2 |
Mr = 587.67 | F(000) = 616 |
Triclinic, P1 | Dx = 1.288 Mg m−3 |
Hall symbol: -P 1 | Melting point: 453 K |
a = 10.922 (5) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 11.661 (5) Å | Cell parameters from 894 reflections |
c = 13.641 (6) Å | θ = 2.8–25.9° |
α = 86.619 (5)° | µ = 0.64 mm−1 |
β = 79.750 (5)° | T = 293 K |
γ = 62.441 (5)° | Block, colourless |
V = 1515.2 (11) Å3 | 0.15 × 0.12 × 0.10 mm |
Bruker APEXII CCD diffractometer | 5438 independent reflections |
Radiation source: fine-focus sealed tube | 4323 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.022 |
φ and ω scans | θmax = 25.4°, θmin = 1.5° |
Absorption correction: multi-scan (SADABS; Bruker, 2009) | h = −12→13 |
Tmin = 0.910, Tmax = 0.938 | k = −14→14 |
6963 measured reflections | l = −16→16 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.041 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.102 | H-atom parameters constrained |
S = 1.00 | w = 1/[σ2(Fo2) + (0.0595P)2] where P = (Fo2 + 2Fc2)/3 |
5438 reflections | (Δ/σ)max = 0.001 |
335 parameters | Δρmax = 0.73 e Å−3 |
36 restraints | Δρmin = −0.29 e Å−3 |
[Ru(C10H18N2P)2(C7H8)] | γ = 62.441 (5)° |
Mr = 587.67 | V = 1515.2 (11) Å3 |
Triclinic, P1 | Z = 2 |
a = 10.922 (5) Å | Mo Kα radiation |
b = 11.661 (5) Å | µ = 0.64 mm−1 |
c = 13.641 (6) Å | T = 293 K |
α = 86.619 (5)° | 0.15 × 0.12 × 0.10 mm |
β = 79.750 (5)° |
Bruker APEXII CCD diffractometer | 5438 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2009) | 4323 reflections with I > 2σ(I) |
Tmin = 0.910, Tmax = 0.938 | Rint = 0.022 |
6963 measured reflections |
R[F2 > 2σ(F2)] = 0.041 | 36 restraints |
wR(F2) = 0.102 | H-atom parameters constrained |
S = 1.00 | Δρmax = 0.73 e Å−3 |
5438 reflections | Δρmin = −0.29 e Å−3 |
335 parameters |
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 | 0.97741 (3) | 0.75701 (3) | 0.69344 (2) | 0.04137 (11) | |
P1 | 0.64266 (12) | 1.08096 (10) | 0.55908 (8) | 0.0570 (3) | |
P2 | 0.74186 (13) | 0.68084 (12) | 0.96868 (8) | 0.0676 (3) | |
N1 | 0.8569 (3) | 0.8730 (3) | 0.5912 (2) | 0.0471 (7) | |
N2 | 0.8111 (3) | 0.9430 (3) | 0.6770 (2) | 0.0483 (7) | |
N3 | 0.8358 (3) | 0.7021 (3) | 0.7873 (2) | 0.0499 (7) | |
N4 | 0.9151 (3) | 0.7239 (3) | 0.8407 (2) | 0.0507 (8) | |
C1 | 0.7819 (4) | 0.9295 (3) | 0.5202 (3) | 0.0462 (8) | |
C2 | 0.8208 (5) | 0.8601 (4) | 0.4197 (3) | 0.0555 (10) | |
C3 | 0.9706 (5) | 0.8301 (5) | 0.3733 (3) | 0.0777 (14) | |
H3A | 0.9949 | 0.7866 | 0.3099 | 0.117* | |
H3B | 1.0337 | 0.7755 | 0.4165 | 0.117* | |
H3C | 0.9775 | 0.9093 | 0.3643 | 0.117* | |
C4 | 0.7207 (5) | 0.9482 (4) | 0.3512 (3) | 0.0724 (13) | |
H4A | 0.7447 | 0.9053 | 0.2875 | 0.109* | |
H4B | 0.7281 | 1.0272 | 0.3427 | 0.109* | |
H4C | 0.6263 | 0.9674 | 0.3803 | 0.109* | |
C5 | 0.8029 (7) | 0.7370 (4) | 0.4348 (4) | 0.0942 (18) | |
H5A | 0.8273 | 0.6926 | 0.3717 | 0.141* | |
H5B | 0.7072 | 0.7598 | 0.4626 | 0.141* | |
H5C | 0.8630 | 0.6815 | 0.4793 | 0.141* | |
C6 | 0.6988 (4) | 1.0549 (3) | 0.6753 (3) | 0.0478 (9) | |
C7 | 0.6301 (4) | 1.1376 (4) | 0.7697 (3) | 0.0573 (10) | |
C8 | 0.7348 (6) | 1.1659 (5) | 0.8091 (4) | 0.1039 (19) | |
H8A | 0.6899 | 1.2184 | 0.8690 | 0.156* | |
H8B | 0.7692 | 1.2112 | 0.7600 | 0.156* | |
H8C | 0.8116 | 1.0860 | 0.8232 | 0.156* | |
C9 | 0.5068 (6) | 1.2648 (5) | 0.7496 (4) | 0.1033 (19) | |
H9A | 0.4641 | 1.3165 | 0.8100 | 0.155* | |
H9B | 0.4392 | 1.2474 | 0.7260 | 0.155* | |
H9C | 0.5396 | 1.3108 | 0.7000 | 0.155* | |
C10 | 0.5777 (6) | 1.0641 (5) | 0.8472 (4) | 0.0978 (18) | |
H10A | 0.5337 | 1.1155 | 0.9077 | 0.147* | |
H10B | 0.6553 | 0.9842 | 0.8602 | 0.147* | |
H10C | 0.5110 | 1.0463 | 0.8226 | 0.147* | |
C11 | 0.8812 (4) | 0.7183 (4) | 0.9387 (3) | 0.0535 (9) | |
C12 | 0.9547 (5) | 0.7475 (4) | 1.0109 (3) | 0.0688 (12) | |
C13 | 0.9391 (6) | 0.6801 (5) | 1.1093 (3) | 0.0919 (17) | |
H13A | 0.8415 | 0.7110 | 1.1359 | 0.138* | |
H13B | 0.9837 | 0.6991 | 1.1561 | 0.138* | |
H13C | 0.9825 | 0.5883 | 1.0972 | 0.138* | |
C14 | 0.8812 (7) | 0.8946 (5) | 1.0312 (5) | 0.126 (3) | |
H14A | 0.7837 | 0.9231 | 1.0572 | 0.188* | |
H14B | 0.8901 | 0.9377 | 0.9702 | 0.188* | |
H14C | 0.9238 | 0.9149 | 1.0787 | 0.188* | |
C15 | 1.1085 (6) | 0.6987 (6) | 0.9697 (4) | 0.0981 (18) | |
H15A | 1.1526 | 0.7183 | 1.0166 | 0.147* | |
H15B | 1.1188 | 0.7401 | 0.9080 | 0.147* | |
H15C | 1.1519 | 0.6068 | 0.9581 | 0.147* | |
C16 | 0.7396 (4) | 0.6784 (4) | 0.8408 (3) | 0.0530 (9) | |
C17 | 0.6415 (5) | 0.6519 (4) | 0.7904 (4) | 0.0709 (12) | |
C21 | 1.1543 (4) | 0.5732 (3) | 0.6960 (3) | 0.0544 (10) | |
H21 | 1.1489 | 0.5004 | 0.7327 | 0.065* | |
C22 | 1.1300 (4) | 0.5984 (3) | 0.5981 (3) | 0.0539 (10) | |
H22 | 1.1057 | 0.5452 | 0.5603 | 0.065* | |
C23 | 1.2215 (4) | 0.6608 (4) | 0.5502 (3) | 0.0586 (10) | |
H23 | 1.2396 | 0.6620 | 0.4773 | 0.070* | |
C24 | 1.3504 (4) | 0.5920 (5) | 0.6037 (3) | 0.0735 (12) | |
H24A | 1.4040 | 0.5003 | 0.5871 | 0.088* | |
H24B | 1.4111 | 0.6330 | 0.5931 | 0.088* | |
C25 | 1.2607 (4) | 0.6204 (4) | 0.7078 (3) | 0.0613 (11) | |
H25 | 1.3101 | 0.5890 | 0.7648 | 0.074* | |
C26 | 1.1641 (4) | 0.7663 (4) | 0.7051 (3) | 0.0551 (10) | |
H26 | 1.1656 | 0.8296 | 0.7484 | 0.066* | |
C27 | 1.1412 (4) | 0.7915 (4) | 0.6065 (3) | 0.0518 (9) | |
H27 | 1.1243 | 0.8739 | 0.5749 | 0.062* | |
C18 | 0.7298 (8) | 0.5446 (8) | 0.7118 (7) | 0.112 (3) | 0.719 (6) |
H18A | 0.7735 | 0.4635 | 0.7439 | 0.168* | 0.719 (6) |
H18B | 0.8007 | 0.5628 | 0.6726 | 0.168* | 0.719 (6) |
H18C | 0.6710 | 0.5398 | 0.6693 | 0.168* | 0.719 (6) |
C19 | 0.5422 (10) | 0.7740 (8) | 0.7461 (9) | 0.122 (3) | 0.719 (6) |
H19A | 0.4621 | 0.8224 | 0.7958 | 0.184* | 0.719 (6) |
H19B | 0.5123 | 0.7521 | 0.6911 | 0.184* | 0.719 (6) |
H19C | 0.5890 | 0.8254 | 0.7231 | 0.184* | 0.719 (6) |
C20 | 0.5612 (9) | 0.5975 (10) | 0.8662 (7) | 0.121 (3) | 0.719 (6) |
H20A | 0.6193 | 0.5474 | 0.9137 | 0.181* | 0.719 (6) |
H20B | 0.5367 | 0.5433 | 0.8320 | 0.181* | 0.719 (6) |
H20C | 0.4775 | 0.6676 | 0.9002 | 0.181* | 0.719 (6) |
C18' | 0.4912 (16) | 0.740 (2) | 0.8434 (19) | 0.122 (3) | 0.281 (6) |
H18D | 0.4768 | 0.7088 | 0.9091 | 0.182* | 0.281 (6) |
H18E | 0.4252 | 0.7383 | 0.8061 | 0.182* | 0.281 (6) |
H18F | 0.4779 | 0.8266 | 0.8481 | 0.182* | 0.281 (6) |
C20' | 0.629 (3) | 0.723 (2) | 0.6899 (15) | 0.120 (4) | 0.281 (6) |
H20D | 0.7165 | 0.6810 | 0.6450 | 0.181* | 0.281 (6) |
H20E | 0.6069 | 0.8113 | 0.7013 | 0.181* | 0.281 (6) |
H20F | 0.5563 | 0.7198 | 0.6615 | 0.181* | 0.281 (6) |
C19' | 0.667 (3) | 0.5115 (16) | 0.790 (2) | 0.119 (3) | 0.281 (6) |
H19D | 0.6845 | 0.4763 | 0.8547 | 0.179* | 0.281 (6) |
H19E | 0.7476 | 0.4619 | 0.7409 | 0.179* | 0.281 (6) |
H19F | 0.5867 | 0.5081 | 0.7751 | 0.179* | 0.281 (6) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Ru1 | 0.04163 (19) | 0.04155 (17) | 0.03939 (17) | −0.01768 (13) | −0.00559 (12) | −0.00448 (11) |
P1 | 0.0529 (7) | 0.0499 (6) | 0.0562 (6) | −0.0147 (5) | −0.0079 (5) | 0.0067 (5) |
P2 | 0.0661 (8) | 0.0777 (8) | 0.0537 (7) | −0.0345 (7) | 0.0081 (5) | −0.0034 (6) |
N1 | 0.0462 (18) | 0.0443 (16) | 0.0436 (17) | −0.0146 (14) | −0.0053 (14) | −0.0077 (13) |
N2 | 0.0420 (18) | 0.0479 (17) | 0.0447 (17) | −0.0121 (15) | −0.0038 (13) | −0.0096 (13) |
N3 | 0.0477 (19) | 0.064 (2) | 0.0451 (17) | −0.0300 (17) | −0.0102 (14) | −0.0027 (14) |
N4 | 0.053 (2) | 0.0606 (19) | 0.0447 (18) | −0.0307 (17) | −0.0105 (14) | −0.0001 (14) |
C1 | 0.050 (2) | 0.0460 (19) | 0.044 (2) | −0.0233 (18) | −0.0073 (16) | 0.0017 (16) |
C2 | 0.068 (3) | 0.055 (2) | 0.046 (2) | −0.028 (2) | −0.0159 (19) | 0.0010 (17) |
C3 | 0.064 (3) | 0.098 (4) | 0.055 (3) | −0.023 (3) | −0.004 (2) | −0.024 (2) |
C4 | 0.083 (3) | 0.087 (3) | 0.052 (2) | −0.039 (3) | −0.024 (2) | 0.008 (2) |
C5 | 0.163 (6) | 0.070 (3) | 0.071 (3) | −0.066 (4) | −0.040 (3) | 0.008 (2) |
C6 | 0.044 (2) | 0.0405 (19) | 0.051 (2) | −0.0156 (17) | 0.0005 (16) | −0.0010 (16) |
C7 | 0.054 (3) | 0.045 (2) | 0.060 (2) | −0.0163 (19) | 0.0055 (19) | −0.0100 (18) |
C8 | 0.095 (4) | 0.117 (5) | 0.100 (4) | −0.049 (4) | 0.005 (3) | −0.056 (3) |
C9 | 0.100 (4) | 0.064 (3) | 0.090 (4) | 0.005 (3) | 0.002 (3) | −0.015 (3) |
C10 | 0.121 (5) | 0.073 (3) | 0.074 (3) | −0.040 (3) | 0.037 (3) | −0.016 (3) |
C11 | 0.061 (3) | 0.052 (2) | 0.042 (2) | −0.022 (2) | −0.0072 (18) | −0.0043 (17) |
C12 | 0.084 (3) | 0.075 (3) | 0.051 (2) | −0.036 (3) | −0.020 (2) | −0.005 (2) |
C13 | 0.108 (4) | 0.111 (4) | 0.045 (3) | −0.036 (4) | −0.021 (3) | −0.004 (3) |
C14 | 0.180 (7) | 0.079 (4) | 0.129 (5) | −0.048 (4) | −0.082 (5) | −0.010 (3) |
C15 | 0.107 (5) | 0.154 (5) | 0.066 (3) | −0.081 (4) | −0.033 (3) | 0.002 (3) |
C16 | 0.043 (2) | 0.051 (2) | 0.062 (2) | −0.0209 (19) | −0.0056 (18) | −0.0002 (18) |
C17 | 0.056 (3) | 0.076 (3) | 0.093 (3) | −0.039 (3) | −0.019 (2) | 0.006 (3) |
C21 | 0.051 (2) | 0.0396 (19) | 0.061 (2) | −0.0114 (18) | −0.0076 (19) | −0.0028 (17) |
C22 | 0.057 (3) | 0.0381 (19) | 0.057 (2) | −0.0144 (18) | −0.0014 (19) | −0.0144 (17) |
C23 | 0.047 (2) | 0.062 (2) | 0.053 (2) | −0.015 (2) | 0.0001 (18) | −0.0096 (19) |
C24 | 0.045 (3) | 0.077 (3) | 0.079 (3) | −0.016 (2) | 0.001 (2) | −0.005 (2) |
C25 | 0.045 (2) | 0.068 (3) | 0.061 (3) | −0.016 (2) | −0.0107 (19) | −0.001 (2) |
C26 | 0.047 (2) | 0.061 (2) | 0.062 (2) | −0.029 (2) | −0.0069 (18) | −0.0069 (19) |
C27 | 0.044 (2) | 0.057 (2) | 0.056 (2) | −0.0276 (19) | 0.0017 (17) | −0.0047 (18) |
C18 | 0.091 (5) | 0.106 (5) | 0.163 (7) | −0.055 (4) | −0.037 (5) | −0.040 (5) |
C19 | 0.088 (6) | 0.110 (5) | 0.182 (8) | −0.039 (5) | −0.076 (5) | 0.008 (5) |
C20 | 0.089 (5) | 0.123 (5) | 0.175 (7) | −0.063 (4) | −0.038 (4) | −0.003 (5) |
C18' | 0.085 (5) | 0.119 (5) | 0.179 (7) | −0.051 (5) | −0.055 (5) | 0.001 (5) |
C20' | 0.087 (7) | 0.114 (7) | 0.180 (9) | −0.043 (6) | −0.079 (7) | 0.010 (7) |
C19' | 0.092 (5) | 0.113 (5) | 0.172 (7) | −0.056 (5) | −0.038 (5) | −0.020 (5) |
Ru1—N1 | 2.071 (3) | C13—H13B | 0.9600 |
Ru1—N4 | 2.077 (3) | C13—H13C | 0.9600 |
Ru1—N2 | 2.121 (3) | C14—H14A | 0.9600 |
Ru1—C21 | 2.124 (4) | C14—H14B | 0.9600 |
Ru1—C26 | 2.125 (4) | C14—H14C | 0.9600 |
Ru1—C22 | 2.133 (3) | C15—H15A | 0.9600 |
Ru1—N3 | 2.135 (3) | C15—H15B | 0.9600 |
Ru1—C27 | 2.150 (4) | C15—H15C | 0.9600 |
P1—C1 | 1.747 (4) | C16—C17 | 1.520 (6) |
P1—C6 | 1.760 (4) | C17—C19 | 1.507 (7) |
P2—C11 | 1.745 (4) | C17—C18 | 1.523 (7) |
P2—C16 | 1.751 (4) | C17—C19' | 1.527 (15) |
N1—C1 | 1.324 (4) | C17—C20 | 1.535 (7) |
N1—N2 | 1.346 (4) | C17—C18' | 1.541 (15) |
N2—C6 | 1.316 (4) | C17—C20' | 1.551 (15) |
N3—C16 | 1.298 (5) | C21—C22 | 1.395 (5) |
N3—N4 | 1.341 (4) | C21—C25 | 1.534 (5) |
N4—C11 | 1.328 (5) | C21—H21 | 0.9800 |
C1—C2 | 1.523 (5) | C22—C23 | 1.529 (5) |
C2—C3 | 1.526 (6) | C22—H22 | 0.9800 |
C2—C4 | 1.529 (5) | C23—C27 | 1.530 (5) |
C2—C5 | 1.534 (6) | C23—C24 | 1.551 (6) |
C3—H3A | 0.9600 | C23—H23 | 0.9800 |
C3—H3B | 0.9600 | C24—C25 | 1.532 (6) |
C3—H3C | 0.9600 | C24—H24A | 0.9700 |
C4—H4A | 0.9600 | C24—H24B | 0.9700 |
C4—H4B | 0.9600 | C25—C26 | 1.534 (5) |
C4—H4C | 0.9600 | C25—H25 | 0.9800 |
C5—H5A | 0.9600 | C26—C27 | 1.400 (5) |
C5—H5B | 0.9600 | C26—H26 | 0.9800 |
C5—H5C | 0.9600 | C27—H27 | 0.9800 |
C6—C7 | 1.512 (5) | C18—H18A | 0.9600 |
C7—C8 | 1.515 (6) | C18—H18B | 0.9600 |
C7—C10 | 1.519 (6) | C18—H18C | 0.9600 |
C7—C9 | 1.525 (6) | C19—H19A | 0.9600 |
C8—H8A | 0.9600 | C19—H19B | 0.9600 |
C8—H8B | 0.9600 | C19—H19C | 0.9600 |
C8—H8C | 0.9600 | C20—H20A | 0.9600 |
C9—H9A | 0.9600 | C20—H20B | 0.9600 |
C9—H9B | 0.9600 | C20—H20C | 0.9600 |
C9—H9C | 0.9600 | C18'—H18D | 0.9600 |
C10—H10A | 0.9600 | C18'—H18E | 0.9600 |
C10—H10B | 0.9600 | C18'—H18F | 0.9600 |
C10—H10C | 0.9600 | C20'—H20D | 0.9600 |
C11—C12 | 1.518 (5) | C20'—H20E | 0.9600 |
C12—C15 | 1.509 (7) | C20'—H20F | 0.9600 |
C12—C13 | 1.537 (6) | C19'—H19D | 0.9600 |
C12—C14 | 1.539 (6) | C19'—H19E | 0.9600 |
C13—H13A | 0.9600 | C19'—H19F | 0.9600 |
N1—Ru1—N4 | 129.37 (12) | H14A—C14—H14B | 109.5 |
N1—Ru1—N2 | 37.44 (11) | C12—C14—H14C | 109.5 |
N4—Ru1—N2 | 100.08 (12) | H14A—C14—H14C | 109.5 |
N1—Ru1—C21 | 138.29 (14) | H14B—C14—H14C | 109.5 |
N4—Ru1—C21 | 85.52 (14) | C12—C15—H15A | 109.5 |
N2—Ru1—C21 | 174.32 (13) | C12—C15—H15B | 109.5 |
N1—Ru1—C26 | 118.31 (14) | H15A—C15—H15B | 109.5 |
N4—Ru1—C26 | 100.32 (14) | C12—C15—H15C | 109.5 |
N2—Ru1—C26 | 111.66 (14) | H15A—C15—H15C | 109.5 |
C21—Ru1—C26 | 66.04 (15) | H15B—C15—H15C | 109.5 |
N1—Ru1—C22 | 100.09 (13) | N3—C16—C17 | 119.9 (4) |
N4—Ru1—C22 | 119.54 (14) | N3—C16—P2 | 112.6 (3) |
N2—Ru1—C22 | 137.02 (13) | C17—C16—P2 | 127.5 (3) |
C21—Ru1—C22 | 38.25 (14) | C19—C17—C16 | 110.1 (5) |
C26—Ru1—C22 | 78.78 (15) | C19—C17—C18 | 112.0 (7) |
N1—Ru1—N3 | 102.47 (12) | C16—C17—C18 | 108.4 (4) |
N4—Ru1—N3 | 37.10 (11) | C19—C17—C19' | 134.1 (10) |
N2—Ru1—N3 | 90.76 (12) | C16—C17—C19' | 115.7 (9) |
C21—Ru1—N3 | 94.32 (14) | C18—C17—C19' | 50.5 (11) |
C26—Ru1—N3 | 136.30 (13) | C19—C17—C20 | 111.1 (6) |
C22—Ru1—N3 | 110.33 (14) | C16—C17—C20 | 109.6 (4) |
N1—Ru1—C27 | 84.55 (14) | C18—C17—C20 | 105.6 (5) |
N4—Ru1—C27 | 138.47 (14) | C19'—C17—C20 | 55.6 (11) |
N2—Ru1—C27 | 96.30 (14) | C19—C17—C18' | 57.0 (10) |
C21—Ru1—C27 | 78.73 (16) | C16—C17—C18' | 106.9 (9) |
C26—Ru1—C27 | 38.23 (15) | C18—C17—C18' | 144.6 (9) |
C22—Ru1—C27 | 65.62 (15) | C19'—C17—C18' | 109.8 (14) |
N3—Ru1—C27 | 172.61 (13) | C20—C17—C18' | 58.8 (10) |
C1—P1—C6 | 87.57 (17) | C19—C17—C20' | 40.4 (9) |
C11—P2—C16 | 87.69 (18) | C16—C17—C20' | 107.5 (9) |
C1—N1—N2 | 114.3 (3) | C18—C17—C20' | 75.5 (11) |
C1—N1—Ru1 | 170.7 (3) | C19'—C17—C20' | 118.1 (15) |
N2—N1—Ru1 | 73.30 (18) | C20—C17—C20' | 140.1 (9) |
C6—N2—N1 | 114.1 (3) | C18'—C17—C20' | 96.7 (14) |
C6—N2—Ru1 | 173.2 (3) | C22—C21—C25 | 106.1 (4) |
N1—N2—Ru1 | 69.26 (17) | C22—C21—Ru1 | 71.2 (2) |
C16—N3—N4 | 114.0 (3) | C25—C21—Ru1 | 98.0 (2) |
C16—N3—Ru1 | 174.2 (3) | C22—C21—H21 | 122.9 |
N4—N3—Ru1 | 69.12 (19) | C25—C21—H21 | 122.9 |
C11—N4—N3 | 114.6 (3) | Ru1—C21—H21 | 122.9 |
C11—N4—Ru1 | 170.1 (3) | C21—C22—C23 | 106.2 (3) |
N3—N4—Ru1 | 73.79 (19) | C21—C22—Ru1 | 70.5 (2) |
N1—C1—C2 | 119.9 (3) | C23—C22—Ru1 | 98.2 (2) |
N1—C1—P1 | 112.0 (3) | C21—C22—H22 | 122.9 |
C2—C1—P1 | 128.1 (3) | C23—C22—H22 | 122.9 |
C1—C2—C3 | 109.5 (3) | Ru1—C22—H22 | 122.9 |
C1—C2—C4 | 108.9 (3) | C22—C23—C27 | 98.7 (3) |
C3—C2—C4 | 109.3 (4) | C22—C23—C24 | 101.6 (3) |
C1—C2—C5 | 108.9 (3) | C27—C23—C24 | 101.5 (3) |
C3—C2—C5 | 111.9 (4) | C22—C23—H23 | 117.3 |
C4—C2—C5 | 108.3 (4) | C27—C23—H23 | 117.3 |
C2—C3—H3A | 109.5 | C24—C23—H23 | 117.3 |
C2—C3—H3B | 109.5 | C25—C24—C23 | 93.6 (3) |
H3A—C3—H3B | 109.5 | C25—C24—H24A | 113.0 |
C2—C3—H3C | 109.5 | C23—C24—H24A | 113.0 |
H3A—C3—H3C | 109.5 | C25—C24—H24B | 113.0 |
H3B—C3—H3C | 109.5 | C23—C24—H24B | 113.0 |
C2—C4—H4A | 109.5 | H24A—C24—H24B | 110.4 |
C2—C4—H4B | 109.5 | C24—C25—C21 | 101.8 (3) |
H4A—C4—H4B | 109.5 | C24—C25—C26 | 102.1 (3) |
C2—C4—H4C | 109.5 | C21—C25—C26 | 98.0 (3) |
H4A—C4—H4C | 109.5 | C24—C25—H25 | 117.3 |
H4B—C4—H4C | 109.5 | C21—C25—H25 | 117.3 |
C2—C5—H5A | 109.5 | C26—C25—H25 | 117.3 |
C2—C5—H5B | 109.5 | C27—C26—C25 | 106.0 (3) |
H5A—C5—H5B | 109.5 | C27—C26—Ru1 | 71.8 (2) |
C2—C5—H5C | 109.5 | C25—C26—Ru1 | 97.9 (2) |
H5A—C5—H5C | 109.5 | C27—C26—H26 | 122.8 |
H5B—C5—H5C | 109.5 | C25—C26—H26 | 122.8 |
N2—C6—C7 | 119.1 (3) | Ru1—C26—H26 | 122.8 |
N2—C6—P1 | 112.0 (3) | C26—C27—C23 | 106.1 (3) |
C7—C6—P1 | 128.7 (3) | C26—C27—Ru1 | 69.9 (2) |
C6—C7—C8 | 110.3 (4) | C23—C27—Ru1 | 97.5 (2) |
C6—C7—C10 | 108.5 (3) | C26—C27—H27 | 123.2 |
C8—C7—C10 | 109.2 (4) | C23—C27—H27 | 123.2 |
C6—C7—C9 | 110.2 (4) | Ru1—C27—H27 | 123.2 |
C8—C7—C9 | 109.2 (4) | C17—C18—H18A | 109.5 |
C10—C7—C9 | 109.4 (4) | C17—C18—H18B | 109.5 |
C7—C8—H8A | 109.5 | H18A—C18—H18B | 109.5 |
C7—C8—H8B | 109.5 | C17—C18—H18C | 109.5 |
H8A—C8—H8B | 109.5 | H18A—C18—H18C | 109.5 |
C7—C8—H8C | 109.5 | H18B—C18—H18C | 109.5 |
H8A—C8—H8C | 109.5 | C17—C19—H19A | 109.5 |
H8B—C8—H8C | 109.5 | C17—C19—H19B | 109.5 |
C7—C9—H9A | 109.5 | H19A—C19—H19B | 109.5 |
C7—C9—H9B | 109.5 | C17—C19—H19C | 109.5 |
H9A—C9—H9B | 109.5 | H19A—C19—H19C | 109.5 |
C7—C9—H9C | 109.5 | H19B—C19—H19C | 109.5 |
H9A—C9—H9C | 109.5 | C17—C20—H20A | 109.5 |
H9B—C9—H9C | 109.5 | C17—C20—H20B | 109.5 |
C7—C10—H10A | 109.5 | H20A—C20—H20B | 109.5 |
C7—C10—H10B | 109.5 | C17—C20—H20C | 109.5 |
H10A—C10—H10B | 109.5 | H20A—C20—H20C | 109.5 |
C7—C10—H10C | 109.5 | H20B—C20—H20C | 109.5 |
H10A—C10—H10C | 109.5 | C17—C18'—H18D | 109.5 |
H10B—C10—H10C | 109.5 | C17—C18'—H18E | 109.5 |
N4—C11—C12 | 121.8 (4) | H18D—C18'—H18E | 109.5 |
N4—C11—P2 | 111.1 (3) | C17—C18'—H18F | 109.5 |
C12—C11—P2 | 127.0 (3) | H18D—C18'—H18F | 109.5 |
C15—C12—C11 | 111.1 (4) | H18E—C18'—H18F | 109.5 |
C15—C12—C13 | 109.2 (4) | C17—C20'—H20D | 109.5 |
C11—C12—C13 | 108.5 (4) | C17—C20'—H20E | 109.5 |
C15—C12—C14 | 111.2 (5) | H20D—C20'—H20E | 109.5 |
C11—C12—C14 | 108.1 (4) | C17—C20'—H20F | 109.5 |
C13—C12—C14 | 108.8 (4) | H20D—C20'—H20F | 109.5 |
C12—C13—H13A | 109.5 | H20E—C20'—H20F | 109.5 |
C12—C13—H13B | 109.5 | C17—C19'—H19D | 109.5 |
H13A—C13—H13B | 109.5 | C17—C19'—H19E | 109.5 |
C12—C13—H13C | 109.5 | H19D—C19'—H19E | 109.5 |
H13A—C13—H13C | 109.5 | C17—C19'—H19F | 109.5 |
H13B—C13—H13C | 109.5 | H19D—C19'—H19F | 109.5 |
C12—C14—H14A | 109.5 | H19E—C19'—H19F | 109.5 |
C12—C14—H14B | 109.5 | ||
N4—Ru1—N1—C1 | −100.0 (17) | Ru1—N3—C16—C17 | 59 (3) |
N2—Ru1—N1—C1 | −145.6 (18) | N4—N3—C16—P2 | −0.4 (4) |
C21—Ru1—N1—C1 | 40.3 (18) | Ru1—N3—C16—P2 | −122 (3) |
C26—Ru1—N1—C1 | 125.2 (17) | C11—P2—C16—N3 | 0.7 (3) |
C22—Ru1—N1—C1 | 42.6 (17) | C11—P2—C16—C17 | −179.6 (4) |
N3—Ru1—N1—C1 | −71.1 (17) | N3—C16—C17—C19 | −70.2 (7) |
C27—Ru1—N1—C1 | 106.6 (17) | P2—C16—C17—C19 | 110.2 (6) |
N4—Ru1—N1—N2 | 45.6 (2) | N3—C16—C17—C18 | 52.6 (6) |
C21—Ru1—N1—N2 | −174.1 (2) | P2—C16—C17—C18 | −127.0 (5) |
C26—Ru1—N1—N2 | −89.2 (2) | N3—C16—C17—C19' | 106.9 (14) |
C22—Ru1—N1—N2 | −171.8 (2) | P2—C16—C17—C19' | −72.7 (14) |
N3—Ru1—N1—N2 | 74.5 (2) | N3—C16—C17—C20 | 167.3 (5) |
C27—Ru1—N1—N2 | −107.8 (2) | P2—C16—C17—C20 | −12.3 (6) |
C1—N1—N2—C6 | 0.6 (5) | N3—C16—C17—C18' | −130.4 (12) |
Ru1—N1—N2—C6 | −173.6 (3) | P2—C16—C17—C18' | 50.0 (12) |
C1—N1—N2—Ru1 | 174.3 (3) | N3—C16—C17—C20' | −27.5 (12) |
N1—Ru1—N2—C6 | 121 (2) | P2—C16—C17—C20' | 152.9 (11) |
N4—Ru1—N2—C6 | −25 (2) | N1—Ru1—C21—C22 | 3.6 (3) |
C21—Ru1—N2—C6 | 164 (2) | N4—Ru1—C21—C22 | 153.9 (2) |
C26—Ru1—N2—C6 | −131 (2) | N2—Ru1—C21—C22 | −35.5 (14) |
C22—Ru1—N2—C6 | 133 (2) | C26—Ru1—C21—C22 | −102.7 (3) |
N3—Ru1—N2—C6 | 11 (2) | N3—Ru1—C21—C22 | 117.8 (2) |
C27—Ru1—N2—C6 | −167 (2) | C27—Ru1—C21—C22 | −64.7 (2) |
N4—Ru1—N2—N1 | −145.86 (19) | N1—Ru1—C21—C25 | 108.0 (3) |
C21—Ru1—N2—N1 | 43.7 (14) | N4—Ru1—C21—C25 | −101.7 (2) |
C26—Ru1—N2—N1 | 108.7 (2) | N2—Ru1—C21—C25 | 68.9 (14) |
C22—Ru1—N2—N1 | 11.8 (3) | C26—Ru1—C21—C25 | 1.7 (2) |
N3—Ru1—N2—N1 | −109.7 (2) | C22—Ru1—C21—C25 | 104.4 (3) |
C27—Ru1—N2—N1 | 72.5 (2) | N3—Ru1—C21—C25 | −137.8 (2) |
N1—Ru1—N3—C16 | −18 (3) | C27—Ru1—C21—C25 | 39.7 (2) |
N4—Ru1—N3—C16 | 123 (3) | C25—C21—C22—C23 | 0.1 (4) |
N2—Ru1—N3—C16 | 17 (3) | Ru1—C21—C22—C23 | 93.2 (2) |
C21—Ru1—N3—C16 | −160 (3) | C25—C21—C22—Ru1 | −93.1 (3) |
C26—Ru1—N3—C16 | 141 (3) | N1—Ru1—C22—C21 | −177.6 (2) |
C22—Ru1—N3—C16 | −124 (3) | N4—Ru1—C22—C21 | −30.3 (3) |
C27—Ru1—N3—C16 | −180 (100) | N2—Ru1—C22—C21 | 175.2 (2) |
N1—Ru1—N3—N4 | −141.70 (19) | C26—Ru1—C22—C21 | 65.3 (2) |
N2—Ru1—N3—N4 | −105.8 (2) | N3—Ru1—C22—C21 | −70.1 (3) |
C21—Ru1—N3—N4 | 76.7 (2) | C27—Ru1—C22—C21 | 103.2 (3) |
C26—Ru1—N3—N4 | 17.4 (3) | N1—Ru1—C22—C23 | 78.1 (2) |
C22—Ru1—N3—N4 | 112.4 (2) | N4—Ru1—C22—C23 | −134.6 (2) |
C27—Ru1—N3—N4 | 56.9 (10) | N2—Ru1—C22—C23 | 70.8 (3) |
C16—N3—N4—C11 | −0.4 (5) | C21—Ru1—C22—C23 | −104.3 (3) |
Ru1—N3—N4—C11 | 174.4 (3) | C26—Ru1—C22—C23 | −39.0 (2) |
C16—N3—N4—Ru1 | −174.7 (3) | N3—Ru1—C22—C23 | −174.4 (2) |
N1—Ru1—N4—C11 | −97.4 (16) | C27—Ru1—C22—C23 | −1.1 (2) |
N2—Ru1—N4—C11 | −71.2 (16) | C21—C22—C23—C27 | −70.6 (3) |
C21—Ru1—N4—C11 | 107.9 (16) | Ru1—C22—C23—C27 | 1.5 (3) |
C26—Ru1—N4—C11 | 43.2 (16) | C21—C22—C23—C24 | 33.1 (4) |
C22—Ru1—N4—C11 | 126.1 (16) | Ru1—C22—C23—C24 | 105.1 (3) |
N3—Ru1—N4—C11 | −148.9 (17) | C22—C23—C24—C25 | −50.5 (4) |
C27—Ru1—N4—C11 | 40.5 (17) | C27—C23—C24—C25 | 50.9 (4) |
N1—Ru1—N4—N3 | 51.5 (2) | C23—C24—C25—C21 | 50.5 (4) |
N2—Ru1—N4—N3 | 77.7 (2) | C23—C24—C25—C26 | −50.4 (4) |
C21—Ru1—N4—N3 | −103.2 (2) | C22—C21—C25—C24 | −33.7 (4) |
C26—Ru1—N4—N3 | −167.9 (2) | Ru1—C21—C25—C24 | −106.4 (3) |
C22—Ru1—N4—N3 | −85.0 (2) | C22—C21—C25—C26 | 70.5 (3) |
C27—Ru1—N4—N3 | −170.6 (2) | Ru1—C21—C25—C26 | −2.2 (3) |
N2—N1—C1—C2 | −179.1 (3) | C24—C25—C26—C27 | 32.9 (4) |
Ru1—N1—C1—C2 | −35.5 (19) | C21—C25—C26—C27 | −71.1 (4) |
N2—N1—C1—P1 | −0.1 (4) | C24—C25—C26—Ru1 | 106.1 (3) |
Ru1—N1—C1—P1 | 143.5 (16) | C21—C25—C26—Ru1 | 2.2 (3) |
C6—P1—C1—N1 | −0.3 (3) | N1—Ru1—C26—C27 | −30.9 (3) |
C6—P1—C1—C2 | 178.6 (4) | N4—Ru1—C26—C27 | −177.0 (2) |
N1—C1—C2—C3 | −58.8 (5) | N2—Ru1—C26—C27 | −71.7 (2) |
P1—C1—C2—C3 | 122.4 (4) | C21—Ru1—C26—C27 | 102.6 (3) |
N1—C1—C2—C4 | −178.2 (3) | C22—Ru1—C26—C27 | 64.6 (2) |
P1—C1—C2—C4 | 3.0 (5) | N3—Ru1—C26—C27 | 172.4 (2) |
N1—C1—C2—C5 | 63.9 (5) | N1—Ru1—C26—C25 | −135.2 (2) |
P1—C1—C2—C5 | −114.9 (4) | N4—Ru1—C26—C25 | 78.6 (2) |
N1—N2—C6—C7 | 175.0 (3) | N2—Ru1—C26—C25 | −176.1 (2) |
Ru1—N2—C6—C7 | 57 (2) | C21—Ru1—C26—C25 | −1.7 (2) |
N1—N2—C6—P1 | −0.8 (4) | C22—Ru1—C26—C25 | −39.7 (2) |
Ru1—N2—C6—P1 | −119 (2) | N3—Ru1—C26—C25 | 68.1 (3) |
C1—P1—C6—N2 | 0.6 (3) | C27—Ru1—C26—C25 | −104.3 (3) |
C1—P1—C6—C7 | −174.7 (4) | C25—C26—C27—C23 | 1.0 (4) |
N2—C6—C7—C8 | 56.7 (5) | Ru1—C26—C27—C23 | −92.2 (3) |
P1—C6—C7—C8 | −128.3 (4) | C25—C26—C27—Ru1 | 93.3 (3) |
N2—C6—C7—C10 | −62.9 (5) | C22—C23—C27—C26 | 69.8 (4) |
P1—C6—C7—C10 | 112.1 (4) | C24—C23—C27—C26 | −34.0 (4) |
N2—C6—C7—C9 | 177.3 (4) | C22—C23—C27—Ru1 | −1.4 (3) |
P1—C6—C7—C9 | −7.7 (5) | C24—C23—C27—Ru1 | −105.2 (3) |
N3—N4—C11—C12 | −176.7 (4) | N1—Ru1—C27—C26 | 153.0 (2) |
Ru1—N4—C11—C12 | −29.8 (18) | N4—Ru1—C27—C26 | 4.4 (3) |
N3—N4—C11—P2 | 0.9 (4) | N2—Ru1—C27—C26 | 117.4 (2) |
Ru1—N4—C11—P2 | 147.8 (15) | C21—Ru1—C27—C26 | −65.4 (2) |
C16—P2—C11—N4 | −0.9 (3) | C22—Ru1—C27—C26 | −103.3 (3) |
C16—P2—C11—C12 | 176.5 (4) | N3—Ru1—C27—C26 | −45.2 (10) |
N4—C11—C12—C15 | −36.6 (6) | N1—Ru1—C27—C23 | −102.6 (2) |
P2—C11—C12—C15 | 146.2 (4) | N4—Ru1—C27—C23 | 108.9 (3) |
N4—C11—C12—C13 | −156.6 (4) | N2—Ru1—C27—C23 | −138.2 (2) |
P2—C11—C12—C13 | 26.2 (5) | C21—Ru1—C27—C23 | 39.0 (2) |
N4—C11—C12—C14 | 85.6 (5) | C26—Ru1—C27—C23 | 104.4 (3) |
P2—C11—C12—C14 | −91.6 (5) | C22—Ru1—C27—C23 | 1.1 (2) |
N4—N3—C16—C17 | 180.0 (3) | N3—Ru1—C27—C23 | 59.2 (10) |
Experimental details
Crystal data | |
Chemical formula | [Ru(C10H18N2P)2(C7H8)] |
Mr | 587.67 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 293 |
a, b, c (Å) | 10.922 (5), 11.661 (5), 13.641 (6) |
α, β, γ (°) | 86.619 (5), 79.750 (5), 62.441 (5) |
V (Å3) | 1515.2 (11) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.64 |
Crystal size (mm) | 0.15 × 0.12 × 0.10 |
Data collection | |
Diffractometer | Bruker APEXII CCD |
Absorption correction | Multi-scan (SADABS; Bruker, 2009) |
Tmin, Tmax | 0.910, 0.938 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 6963, 5438, 4323 |
Rint | 0.022 |
(sin θ/λ)max (Å−1) | 0.602 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.041, 0.102, 1.00 |
No. of reflections | 5438 |
No. of parameters | 335 |
No. of restraints | 36 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.73, −0.29 |
Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL2014 (Sheldrick, 2015), SHELXTL (Sheldrick, 2008), publCIF (Westrip, 2010).
Acknowledgements
This work was supported by the National Natural Science Foundation of China (NSFC; grant No. 21272143).
References
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