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metal-organic compounds
In the title complex, [RuClH(C14H20N2O)(C44H32P2)]·C6H6, the RuII ion is in a slightly distorted coordination environment. One of the amino H atoms is involved in a weak intramolecular N—HCl interaction (HCl = 2.71 Å), while the other is involved in an intramolecular N—Hπ(arene) interaction (NHCg = 2.62 Å, where Cg is the centroid of a benzene ring).
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806053815/bh2065sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806053815/bh2065Isup2.hkl |
CCDC reference: 633603
Key indicators
- Single-crystal X-ray study
- T = 150 K
- Mean (C-C) = 0.007 Å
- R factor = 0.051
- wR factor = 0.129
- Data-to-parameter ratio = 16.6
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT180_ALERT_3_C Check Cell Rounding: # of Values Ending with 0 = 4 PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.73 Ratio PLAT331_ALERT_2_C Small Average Phenyl C-C Dist. C1S -C6S 1.37 Ang. PLAT410_ALERT_2_C Short Intra H...H Contact H1RU .. H52A .. 1.96 Ang. PLAT420_ALERT_2_C D-H Without Acceptor N1 - H1A ... ? PLAT420_ALERT_2_C D-H Without Acceptor N1 - H1B ... ? PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 7 PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 2 C6 H6
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 27.57 From the CIF: _reflns_number_total 10692 Count of symmetry unique reflns 6308 Completeness (_total/calc) 169.50% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 4384 Fraction of Friedel pairs measured 0.695 Are heavy atom types Z>Si present yes PLAT791_ALERT_1_G Confirm the Absolute Configuration of C58 = . S PLAT791_ALERT_1_G Confirm the Absolute Configuration of C62 = . R PLAT791_ALERT_1_G Confirm the Absolute Configuration of C63 = . R
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 8 ALERT level C = Check and explain 4 ALERT level G = General alerts; check 3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 5 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 3 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
Computing details top
Data collection: COLLECT (Nonius, 2002); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO-SMN; program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXTL/PC (Sheldrick, 2001); molecular graphics: SHELXTL/PC; software used to prepare material for publication: SHELXTL/PC.
[(R)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl-κ2P,P']chlorohydrido{(S)-
2-methyl-1-[(4R,5R)-4-methyl-5-phenyl-4,5-dihydrooxazol-2-yl]propan-1- amineκ2N,N'}ruthenium(II) benzene solvate top
Crystal data top
[RuClH(C14H20N2O)(C44H32P2)]·C6H6 | F(000) = 2224 |
Mr = 1070.59 | Dx = 1.375 Mg m−3 |
Monoclinic, C2 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: C 2y | Cell parameters from 20470 reflections |
a = 24.9500 (6) Å | θ = 2.6–27.5° |
b = 10.7370 (3) Å | µ = 0.46 mm−1 |
c = 19.4560 (4) Å | T = 150 K |
β = 96.9780 (16)° | Needle, orange |
V = 5173.4 (2) Å3 | 0.22 × 0.12 × 0.10 mm |
Z = 4 |
Data collection top
Bruker–Nonius KappaCCD diffractometer | 10692 independent reflections |
Radiation source: fine-focus sealed tube | 9051 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.058 |
Detector resolution: 9 pixels mm-1 | θmax = 27.6°, θmin = 2.8° |
φ scans and ω scans with κ offsets | h = −32→32 |
Absorption correction: multi-scan (SORTAV; Blessing, 1995) | k = −13→12 |
Tmin = 0.928, Tmax = 0.957 | l = −25→25 |
20470 measured reflections |
Refinement top
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.051 | w = 1/[σ2(Fo2) + (0.0653P)2] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.129 | (Δ/σ)max = 0.001 |
S = 1.04 | Δρmax = 1.48 e Å−3 |
10692 reflections | Δρmin = −1.12 e Å−3 |
645 parameters | Extinction correction: SHELXTL/PC, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
1 restraint | Extinction coefficient: 0.0015 (3) |
Primary atom site location: structure-invariant direct methods | Absolute structure: Flack (1983), 4433 Friedel pairs |
Secondary atom site location: difference Fourier map | Absolute structure parameter: −0.05 (3) |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | ||
Ru1 | 0.805282 (12) | 0.06201 (3) | 0.320736 (14) | 0.02510 (10) | |
H1RU | 0.788 (2) | 0.202 (6) | 0.354 (3) | 0.043 (14)* | |
Cl1 | 0.83495 (5) | −0.16363 (11) | 0.30382 (6) | 0.0369 (3) | |
P1 | 0.80165 (4) | 0.13654 (11) | 0.21255 (5) | 0.0244 (2) | |
P2 | 0.71500 (4) | 0.05063 (13) | 0.31219 (5) | 0.0254 (2) | |
O1 | 0.94308 (14) | 0.1708 (4) | 0.45463 (16) | 0.0434 (9) | |
N1 | 0.81623 (15) | 0.0052 (4) | 0.42941 (18) | 0.0305 (8) | |
H1A | 0.7834 | 0.0058 | 0.4465 | 0.037* | |
H1B | 0.8296 | −0.0747 | 0.4330 | 0.037* | |
N2 | 0.88996 (14) | 0.1032 (4) | 0.35988 (19) | 0.0325 (9) | |
C1 | 0.75690 (15) | 0.0434 (5) | 0.15003 (18) | 0.0264 (9) | |
C2 | 0.77870 (18) | −0.0514 (5) | 0.1096 (2) | 0.0321 (10) | |
H2A | 0.8166 | −0.0545 | 0.1080 | 0.039* | |
C3 | 0.7462 (2) | −0.1379 (5) | 0.0731 (2) | 0.0338 (10) | |
H3A | 0.7619 | −0.1994 | 0.0467 | 0.041* | |
C4 | 0.68940 (19) | −0.1370 (4) | 0.0740 (2) | 0.0303 (9) | |
C5 | 0.6553 (2) | −0.2265 (5) | 0.0375 (2) | 0.0383 (11) | |
H5A | 0.6705 | −0.2901 | 0.0119 | 0.046* | |
C6 | 0.6009 (2) | −0.2223 (5) | 0.0387 (2) | 0.0357 (11) | |
H6A | 0.5783 | −0.2823 | 0.0137 | 0.043* | |
C7 | 0.57796 (19) | −0.1289 (5) | 0.0771 (2) | 0.0359 (10) | |
H7A | 0.5399 | −0.1266 | 0.0776 | 0.043* | |
C8 | 0.60963 (18) | −0.0418 (4) | 0.1135 (2) | 0.0304 (9) | |
H8A | 0.5936 | 0.0195 | 0.1397 | 0.036* | |
C9 | 0.66697 (17) | −0.0424 (4) | 0.1123 (2) | 0.0268 (9) | |
C10 | 0.70099 (15) | 0.0492 (5) | 0.14997 (17) | 0.0246 (8) | |
C11 | 0.67647 (16) | 0.1656 (4) | 0.2553 (2) | 0.0280 (9) | |
C12 | 0.64980 (18) | 0.2670 (5) | 0.2836 (2) | 0.0314 (10) | |
H12A | 0.6500 | 0.2736 | 0.3324 | 0.038* | |
C13 | 0.62380 (19) | 0.3552 (5) | 0.2409 (2) | 0.0352 (10) | |
H13A | 0.6068 | 0.4230 | 0.2610 | 0.042* | |
C14 | 0.62142 (18) | 0.3487 (5) | 0.1682 (2) | 0.0327 (10) | |
C15 | 0.5956 (2) | 0.4401 (5) | 0.1235 (3) | 0.0422 (12) | |
H15A | 0.5793 | 0.5097 | 0.1428 | 0.051* | |
C16 | 0.5934 (2) | 0.4309 (5) | 0.0530 (3) | 0.0435 (12) | |
H16A | 0.5749 | 0.4921 | 0.0239 | 0.052* | |
C17 | 0.6188 (2) | 0.3305 (5) | 0.0241 (3) | 0.0356 (11) | |
H17A | 0.6180 | 0.3247 | −0.0247 | 0.043* | |
C18 | 0.64479 (18) | 0.2404 (5) | 0.0656 (2) | 0.0309 (9) | |
H18A | 0.6614 | 0.1728 | 0.0449 | 0.037* | |
C19 | 0.64737 (16) | 0.2456 (4) | 0.1388 (2) | 0.0279 (9) | |
C20 | 0.67461 (16) | 0.1551 (4) | 0.1839 (2) | 0.0249 (8) | |
C21 | 0.86752 (17) | 0.1419 (5) | 0.1774 (2) | 0.0296 (9) | |
C22 | 0.89119 (18) | 0.2543 (5) | 0.1616 (2) | 0.0330 (10) | |
H22A | 0.8720 | 0.3300 | 0.1648 | 0.040* | |
C23 | 0.9427 (2) | 0.2565 (5) | 0.1411 (3) | 0.0409 (12) | |
H23A | 0.9587 | 0.3341 | 0.1321 | 0.049* | |
C24 | 0.97054 (19) | 0.1483 (6) | 0.1336 (3) | 0.0417 (12) | |
H24A | 1.0051 | 0.1507 | 0.1178 | 0.050* | |
C25 | 0.94768 (18) | 0.0338 (5) | 0.1496 (2) | 0.0415 (13) | |
H25A | 0.9665 | −0.0416 | 0.1440 | 0.050* | |
C26 | 0.89742 (18) | 0.0311 (4) | 0.1736 (2) | 0.0341 (11) | |
H26A | 0.8832 | −0.0457 | 0.1875 | 0.041* | |
C31 | 0.77942 (16) | 0.2984 (4) | 0.1928 (2) | 0.0268 (9) | |
C32 | 0.76670 (18) | 0.3364 (5) | 0.1232 (2) | 0.0321 (9) | |
H32A | 0.7674 | 0.2772 | 0.0870 | 0.039* | |
C33 | 0.75336 (19) | 0.4579 (5) | 0.1074 (2) | 0.0352 (10) | |
H33A | 0.7436 | 0.4818 | 0.0605 | 0.042* | |
C34 | 0.75409 (18) | 0.5462 (5) | 0.1597 (2) | 0.0376 (11) | |
H34A | 0.7453 | 0.6306 | 0.1487 | 0.045* | |
C35 | 0.7678 (2) | 0.5103 (5) | 0.2283 (3) | 0.0380 (10) | |
H35A | 0.7688 | 0.5704 | 0.2643 | 0.046* | |
C36 | 0.77998 (18) | 0.3863 (5) | 0.2443 (2) | 0.0313 (9) | |
H36A | 0.7888 | 0.3621 | 0.2913 | 0.038* | |
C37 | 0.66994 (18) | −0.0838 (5) | 0.2866 (2) | 0.0276 (9) | |
C38 | 0.68999 (19) | −0.1972 (5) | 0.2689 (2) | 0.0338 (10) | |
H38A | 0.7278 | −0.2081 | 0.2690 | 0.041* | |
C39 | 0.6549 (2) | −0.2956 (5) | 0.2508 (2) | 0.0384 (11) | |
H39A | 0.6686 | −0.3736 | 0.2378 | 0.046* | |
C40 | 0.5999 (2) | −0.2790 (5) | 0.2519 (2) | 0.0383 (11) | |
H40A | 0.5760 | −0.3467 | 0.2404 | 0.046* | |
C41 | 0.57950 (19) | −0.1657 (5) | 0.2695 (2) | 0.0353 (10) | |
H41A | 0.5417 | −0.1550 | 0.2699 | 0.042* | |
C42 | 0.61433 (19) | −0.0683 (5) | 0.2864 (2) | 0.0359 (10) | |
H42A | 0.6005 | 0.0103 | 0.2981 | 0.043* | |
C51 | 0.69615 (16) | 0.0789 (5) | 0.40100 (19) | 0.0325 (10) | |
C52 | 0.7156 (2) | 0.1852 (5) | 0.4373 (2) | 0.0392 (11) | |
H52A | 0.7331 | 0.2480 | 0.4138 | 0.047* | |
C53 | 0.7098 (2) | 0.2013 (6) | 0.5071 (2) | 0.0479 (13) | |
H53A | 0.7235 | 0.2743 | 0.5306 | 0.058* | |
C54 | 0.6842 (3) | 0.1113 (7) | 0.5420 (3) | 0.0581 (17) | |
H54A | 0.6805 | 0.1223 | 0.5897 | 0.070* | |
C55 | 0.6643 (3) | 0.0062 (7) | 0.5080 (3) | 0.0554 (16) | |
H55A | 0.6463 | −0.0553 | 0.5319 | 0.067* | |
C56 | 0.6706 (2) | −0.0105 (6) | 0.4368 (2) | 0.0435 (12) | |
H56A | 0.6570 | −0.0839 | 0.4135 | 0.052* | |
C57 | 0.89650 (18) | 0.1214 (5) | 0.4257 (2) | 0.0334 (10) | |
C58 | 0.85417 (19) | 0.0911 (5) | 0.4710 (2) | 0.0373 (12) | |
H58A | 0.8339 | 0.1698 | 0.4771 | 0.045* | |
C59 | 0.8767 (2) | 0.0451 (7) | 0.5443 (2) | 0.0488 (14) | |
H59A | 0.9021 | 0.1098 | 0.5660 | 0.059* | |
C60 | 0.9080 (2) | −0.0763 (7) | 0.5411 (3) | 0.0589 (17) | |
H60A | 0.9372 | −0.0646 | 0.5123 | 0.088* | |
H60B | 0.8836 | −0.1419 | 0.5210 | 0.088* | |
H60C | 0.9233 | −0.1006 | 0.5880 | 0.088* | |
C61 | 0.8311 (2) | 0.0305 (6) | 0.5892 (2) | 0.0519 (16) | |
H61A | 0.8459 | 0.0010 | 0.6353 | 0.078* | |
H61B | 0.8047 | −0.0299 | 0.5678 | 0.078* | |
H61C | 0.8133 | 0.1111 | 0.5934 | 0.078* | |
C62 | 0.94339 (19) | 0.1278 (5) | 0.3360 (3) | 0.0371 (11) | |
H62A | 0.9392 | 0.1741 | 0.2911 | 0.045* | |
C63 | 0.97183 (18) | 0.2096 (5) | 0.3954 (2) | 0.0362 (11) | |
H63A | 1.0107 | 0.1850 | 0.4048 | 0.043* | |
C64 | 0.9718 (2) | 0.0052 (6) | 0.3291 (3) | 0.0467 (13) | |
H64A | 0.9524 | −0.0429 | 0.2911 | 0.070* | |
H64B | 0.9725 | −0.0418 | 0.3724 | 0.070* | |
H64C | 1.0088 | 0.0206 | 0.3195 | 0.070* | |
C65 | 0.9680 (2) | 0.3471 (5) | 0.3858 (2) | 0.0386 (11) | |
C66 | 0.9216 (2) | 0.4037 (6) | 0.3507 (3) | 0.0476 (13) | |
H66A | 0.8925 | 0.3535 | 0.3307 | 0.057* | |
C67 | 0.9182 (3) | 0.5313 (6) | 0.3453 (3) | 0.0563 (16) | |
H67A | 0.8868 | 0.5695 | 0.3219 | 0.068* | |
C68 | 0.9611 (3) | 0.6032 (6) | 0.3742 (3) | 0.0651 (19) | |
H68A | 0.9589 | 0.6913 | 0.3700 | 0.078* | |
C69 | 1.0070 (3) | 0.5504 (8) | 0.4091 (3) | 0.0665 (17) | |
H69A | 1.0360 | 0.6013 | 0.4288 | 0.080* | |
C70 | 1.0100 (2) | 0.4222 (6) | 0.4149 (3) | 0.0484 (13) | |
H70A | 1.0413 | 0.3849 | 0.4391 | 0.058* | |
C1S | 0.5159 (3) | 0.2065 (7) | −0.1674 (3) | 0.0572 (15) | |
H1SA | 0.4868 | 0.2497 | −0.1930 | 0.069* | |
C2S | 0.5086 (2) | 0.1539 (6) | −0.1043 (3) | 0.0515 (14) | |
H2SA | 0.4754 | 0.1632 | −0.0855 | 0.062* | |
C3S | 0.5498 (3) | 0.0891 (6) | −0.0701 (3) | 0.0574 (17) | |
H3SA | 0.5450 | 0.0498 | −0.0275 | 0.069* | |
C4S | 0.5986 (3) | 0.0786 (7) | −0.0955 (3) | 0.0646 (19) | |
H4SA | 0.6272 | 0.0328 | −0.0706 | 0.077* | |
C5S | 0.6058 (3) | 0.1356 (7) | −0.1581 (4) | 0.0644 (18) | |
H5SA | 0.6396 | 0.1311 | −0.1758 | 0.077* | |
C6S | 0.5637 (3) | 0.1978 (7) | −0.1934 (3) | 0.0616 (17) | |
H6SA | 0.5679 | 0.2354 | −0.2366 | 0.074* |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
Ru1 | 0.02315 (15) | 0.02614 (17) | 0.02527 (15) | 0.00211 (16) | −0.00004 (10) | 0.00231 (16) |
Cl1 | 0.0333 (6) | 0.0304 (6) | 0.0471 (6) | 0.0062 (5) | 0.0049 (5) | 0.0020 (5) |
P1 | 0.0215 (5) | 0.0256 (6) | 0.0260 (5) | 0.0027 (4) | 0.0020 (4) | 0.0019 (4) |
P2 | 0.0242 (4) | 0.0279 (6) | 0.0241 (4) | 0.0029 (5) | 0.0028 (3) | −0.0005 (5) |
O1 | 0.0373 (18) | 0.058 (2) | 0.0319 (16) | −0.0175 (17) | −0.0085 (13) | 0.0111 (16) |
N1 | 0.0269 (18) | 0.031 (2) | 0.0324 (17) | −0.0013 (16) | −0.0016 (14) | 0.0049 (16) |
N2 | 0.0238 (18) | 0.035 (2) | 0.0372 (19) | −0.0028 (14) | −0.0023 (14) | 0.0095 (15) |
C1 | 0.0253 (18) | 0.030 (3) | 0.0248 (16) | 0.0024 (18) | 0.0042 (13) | 0.0017 (17) |
C2 | 0.027 (2) | 0.039 (3) | 0.031 (2) | 0.0098 (18) | 0.0048 (17) | −0.0060 (19) |
C3 | 0.037 (3) | 0.037 (3) | 0.028 (2) | 0.006 (2) | 0.0040 (17) | −0.0060 (19) |
C4 | 0.035 (2) | 0.027 (2) | 0.028 (2) | −0.0014 (18) | 0.0037 (17) | −0.0001 (18) |
C5 | 0.050 (3) | 0.033 (3) | 0.031 (2) | 0.001 (2) | 0.001 (2) | −0.005 (2) |
C6 | 0.037 (3) | 0.033 (3) | 0.035 (2) | −0.009 (2) | −0.001 (2) | −0.004 (2) |
C7 | 0.032 (2) | 0.036 (3) | 0.039 (2) | −0.008 (2) | 0.0015 (18) | 0.006 (2) |
C8 | 0.026 (2) | 0.030 (2) | 0.036 (2) | −0.0008 (17) | 0.0029 (17) | 0.0000 (19) |
C9 | 0.029 (2) | 0.025 (2) | 0.0254 (19) | 0.0022 (17) | −0.0018 (15) | 0.0021 (17) |
C10 | 0.0253 (17) | 0.026 (2) | 0.0217 (15) | 0.0035 (19) | 0.0014 (12) | 0.0024 (19) |
C11 | 0.0208 (19) | 0.030 (2) | 0.033 (2) | 0.0037 (17) | 0.0014 (16) | −0.0026 (18) |
C12 | 0.028 (2) | 0.033 (3) | 0.032 (2) | 0.0090 (19) | 0.0011 (17) | −0.0056 (19) |
C13 | 0.031 (2) | 0.031 (3) | 0.042 (2) | 0.013 (2) | −0.0024 (19) | −0.007 (2) |
C14 | 0.028 (2) | 0.029 (2) | 0.038 (2) | 0.0012 (18) | −0.0078 (17) | −0.0026 (19) |
C15 | 0.039 (3) | 0.031 (3) | 0.053 (3) | 0.013 (2) | −0.009 (2) | −0.005 (2) |
C16 | 0.049 (3) | 0.033 (3) | 0.044 (3) | 0.009 (2) | −0.012 (2) | 0.003 (2) |
C17 | 0.041 (3) | 0.031 (3) | 0.034 (2) | 0.001 (2) | −0.002 (2) | 0.001 (2) |
C18 | 0.029 (2) | 0.030 (2) | 0.034 (2) | 0.0016 (18) | 0.0030 (17) | 0.0028 (18) |
C19 | 0.021 (2) | 0.027 (2) | 0.035 (2) | −0.0019 (17) | −0.0005 (16) | 0.0000 (17) |
C20 | 0.0195 (18) | 0.026 (2) | 0.0280 (19) | 0.0021 (16) | −0.0005 (15) | 0.0012 (17) |
C21 | 0.026 (2) | 0.036 (3) | 0.0270 (19) | 0.0032 (18) | −0.0003 (16) | 0.0010 (18) |
C22 | 0.026 (2) | 0.032 (3) | 0.041 (2) | 0.0038 (18) | 0.0041 (18) | 0.0084 (19) |
C23 | 0.029 (2) | 0.041 (3) | 0.053 (3) | 0.006 (2) | 0.008 (2) | 0.015 (2) |
C24 | 0.025 (2) | 0.055 (3) | 0.047 (3) | 0.010 (2) | 0.010 (2) | 0.010 (2) |
C25 | 0.027 (2) | 0.053 (4) | 0.045 (2) | 0.011 (2) | 0.0060 (18) | 0.001 (2) |
C26 | 0.029 (2) | 0.037 (3) | 0.037 (2) | 0.0037 (18) | 0.0020 (17) | 0.0030 (18) |
C31 | 0.0184 (19) | 0.028 (2) | 0.033 (2) | 0.0015 (16) | 0.0017 (15) | 0.0049 (17) |
C32 | 0.027 (2) | 0.036 (3) | 0.033 (2) | 0.0030 (19) | 0.0018 (17) | 0.0001 (19) |
C33 | 0.030 (2) | 0.039 (3) | 0.036 (2) | 0.008 (2) | 0.0032 (18) | 0.007 (2) |
C34 | 0.036 (2) | 0.030 (3) | 0.047 (2) | 0.006 (2) | 0.0075 (18) | 0.010 (2) |
C35 | 0.038 (3) | 0.030 (2) | 0.045 (3) | 0.009 (2) | 0.005 (2) | −0.001 (2) |
C36 | 0.029 (2) | 0.032 (3) | 0.032 (2) | 0.0031 (18) | 0.0014 (17) | 0.0018 (18) |
C37 | 0.026 (2) | 0.033 (3) | 0.0236 (19) | −0.0040 (19) | 0.0032 (16) | 0.0022 (17) |
C38 | 0.027 (2) | 0.035 (3) | 0.039 (2) | 0.0047 (19) | 0.0038 (18) | 0.001 (2) |
C39 | 0.040 (3) | 0.030 (3) | 0.045 (3) | −0.003 (2) | 0.006 (2) | −0.002 (2) |
C40 | 0.039 (3) | 0.034 (3) | 0.041 (3) | −0.004 (2) | 0.003 (2) | −0.004 (2) |
C41 | 0.030 (2) | 0.041 (3) | 0.036 (2) | 0.000 (2) | 0.0061 (18) | −0.001 (2) |
C42 | 0.033 (2) | 0.036 (3) | 0.038 (2) | 0.003 (2) | 0.0069 (19) | 0.003 (2) |
C51 | 0.0283 (19) | 0.042 (3) | 0.0271 (17) | 0.005 (2) | 0.0030 (14) | −0.003 (2) |
C52 | 0.046 (3) | 0.039 (3) | 0.032 (2) | 0.012 (2) | 0.002 (2) | −0.002 (2) |
C53 | 0.057 (3) | 0.051 (4) | 0.035 (2) | 0.013 (3) | 0.000 (2) | −0.012 (2) |
C54 | 0.063 (4) | 0.083 (5) | 0.030 (2) | 0.015 (3) | 0.010 (2) | −0.002 (3) |
C55 | 0.062 (4) | 0.075 (4) | 0.032 (3) | −0.010 (3) | 0.017 (2) | −0.007 (3) |
C56 | 0.046 (3) | 0.055 (3) | 0.030 (2) | −0.008 (3) | 0.010 (2) | −0.003 (2) |
C57 | 0.028 (2) | 0.038 (3) | 0.032 (2) | −0.0074 (19) | −0.0064 (17) | 0.0058 (19) |
C58 | 0.041 (2) | 0.042 (3) | 0.0268 (19) | −0.008 (2) | −0.0035 (17) | 0.0043 (18) |
C59 | 0.046 (3) | 0.064 (4) | 0.033 (2) | −0.019 (3) | −0.0089 (18) | 0.004 (3) |
C60 | 0.041 (3) | 0.077 (5) | 0.053 (3) | −0.010 (3) | −0.016 (2) | 0.025 (3) |
C61 | 0.066 (3) | 0.060 (5) | 0.029 (2) | −0.012 (3) | 0.000 (2) | 0.009 (2) |
C62 | 0.026 (2) | 0.043 (3) | 0.041 (2) | 0.004 (2) | −0.0024 (19) | 0.005 (2) |
C63 | 0.023 (2) | 0.046 (3) | 0.037 (2) | −0.003 (2) | −0.0029 (18) | 0.011 (2) |
C64 | 0.038 (3) | 0.049 (3) | 0.052 (3) | 0.004 (2) | −0.004 (2) | 0.007 (2) |
C65 | 0.038 (3) | 0.044 (3) | 0.036 (2) | −0.003 (2) | 0.0101 (19) | 0.005 (2) |
C66 | 0.042 (3) | 0.052 (4) | 0.050 (3) | 0.003 (3) | 0.009 (2) | 0.008 (3) |
C67 | 0.063 (4) | 0.048 (4) | 0.061 (3) | 0.007 (3) | 0.022 (3) | 0.012 (3) |
C68 | 0.101 (6) | 0.036 (3) | 0.063 (4) | −0.005 (3) | 0.029 (4) | 0.001 (3) |
C69 | 0.083 (4) | 0.058 (4) | 0.059 (3) | −0.023 (4) | 0.011 (3) | −0.006 (4) |
C70 | 0.053 (3) | 0.055 (4) | 0.038 (3) | −0.004 (3) | 0.008 (2) | −0.004 (2) |
C1S | 0.049 (3) | 0.056 (4) | 0.064 (4) | 0.011 (3) | −0.001 (3) | 0.001 (3) |
C2S | 0.041 (3) | 0.052 (4) | 0.064 (3) | −0.015 (3) | 0.012 (3) | −0.012 (3) |
C3S | 0.074 (4) | 0.054 (5) | 0.044 (3) | −0.011 (3) | 0.005 (3) | 0.000 (3) |
C4S | 0.063 (4) | 0.057 (4) | 0.068 (3) | 0.024 (3) | −0.018 (3) | −0.025 (4) |
C5S | 0.049 (3) | 0.069 (5) | 0.079 (4) | 0.008 (3) | 0.024 (3) | −0.021 (4) |
C6S | 0.089 (5) | 0.049 (4) | 0.051 (3) | 0.002 (3) | 0.024 (3) | −0.003 (3) |
Geometric parameters (Å, º) top
Ru1—H1RU | 1.71 (6) | C34—C35 | 1.391 (7) |
Ru1—N1 | 2.186 (3) | C34—H34A | 0.9500 |
Ru1—N2 | 2.202 (4) | C35—C36 | 1.393 (7) |
Ru1—P2 | 2.2418 (10) | C35—H35A | 0.9500 |
Ru1—P1 | 2.2434 (10) | C36—H36A | 0.9500 |
Ru1—Cl1 | 2.5661 (12) | C37—C38 | 1.375 (7) |
P1—C1 | 1.843 (4) | C37—C42 | 1.397 (6) |
P1—C31 | 1.850 (5) | C38—C39 | 1.389 (7) |
P1—C21 | 1.856 (4) | C38—H38A | 0.9500 |
P2—C11 | 1.848 (5) | C39—C40 | 1.387 (7) |
P2—C37 | 1.860 (5) | C39—H39A | 0.9500 |
P2—C51 | 1.870 (4) | C40—C41 | 1.378 (7) |
O1—C57 | 1.338 (5) | C40—H40A | 0.9500 |
O1—C63 | 1.489 (6) | C41—C42 | 1.374 (7) |
N1—C58 | 1.488 (6) | C41—H41A | 0.9500 |
N1—H1A | 0.9200 | C42—H42A | 0.9500 |
N1—H1B | 0.9200 | C51—C56 | 1.386 (7) |
N2—C57 | 1.286 (6) | C51—C52 | 1.398 (7) |
N2—C62 | 1.488 (6) | C52—C53 | 1.393 (7) |
C1—C10 | 1.396 (5) | C52—H52A | 0.9500 |
C1—C2 | 1.434 (6) | C53—C54 | 1.381 (9) |
C2—C3 | 1.374 (7) | C53—H53A | 0.9500 |
C2—H2A | 0.9500 | C54—C55 | 1.371 (9) |
C3—C4 | 1.418 (7) | C54—H54A | 0.9500 |
C3—H3A | 0.9500 | C55—C56 | 1.425 (7) |
C4—C9 | 1.415 (6) | C55—H55A | 0.9500 |
C4—C5 | 1.417 (7) | C56—H56A | 0.9500 |
C5—C6 | 1.361 (7) | C57—C58 | 1.491 (7) |
C5—H5A | 0.9500 | C58—C59 | 1.549 (6) |
C6—C7 | 1.412 (7) | C58—H58A | 1.0000 |
C6—H6A | 0.9500 | C59—C60 | 1.525 (11) |
C7—C8 | 1.365 (6) | C59—C61 | 1.525 (7) |
C7—H7A | 0.9500 | C59—H59A | 1.0000 |
C8—C9 | 1.434 (6) | C60—H60A | 0.9800 |
C8—H8A | 0.9500 | C60—H60B | 0.9800 |
C9—C10 | 1.440 (6) | C60—H60C | 0.9800 |
C10—C20 | 1.506 (6) | C61—H61A | 0.9800 |
C11—C20 | 1.389 (6) | C61—H61B | 0.9800 |
C11—C12 | 1.421 (6) | C61—H61C | 0.9800 |
C12—C13 | 1.371 (7) | C62—C64 | 1.508 (7) |
C12—H12A | 0.9500 | C62—C63 | 1.554 (7) |
C13—C14 | 1.410 (7) | C62—H62A | 1.0000 |
C13—H13A | 0.9500 | C63—C65 | 1.490 (8) |
C14—C15 | 1.415 (7) | C63—H63A | 1.0000 |
C14—C19 | 1.436 (6) | C64—H64A | 0.9800 |
C15—C16 | 1.370 (7) | C64—H64B | 0.9800 |
C15—H15A | 0.9500 | C64—H64C | 0.9800 |
C16—C17 | 1.403 (7) | C65—C70 | 1.387 (8) |
C16—H16A | 0.9500 | C65—C66 | 1.408 (8) |
C17—C18 | 1.371 (7) | C66—C67 | 1.375 (9) |
C17—H17A | 0.9500 | C66—H66A | 0.9500 |
C18—C19 | 1.419 (6) | C67—C68 | 1.383 (10) |
C18—H18A | 0.9500 | C67—H67A | 0.9500 |
C19—C20 | 1.426 (6) | C68—C69 | 1.380 (11) |
C21—C22 | 1.395 (7) | C68—H68A | 0.9500 |
C21—C26 | 1.410 (6) | C69—C70 | 1.383 (11) |
C22—C23 | 1.390 (6) | C69—H69A | 0.9500 |
C22—H22A | 0.9500 | C70—H70A | 0.9500 |
C23—C24 | 1.370 (8) | C1S—C6S | 1.354 (9) |
C23—H23A | 0.9500 | C1S—C2S | 1.385 (9) |
C24—C25 | 1.406 (8) | C1S—H1SA | 0.9500 |
C24—H24A | 0.9500 | C2S—C3S | 1.348 (9) |
C25—C26 | 1.391 (6) | C2S—H2SA | 0.9500 |
C25—H25A | 0.9500 | C3S—C4S | 1.373 (9) |
C26—H26A | 0.9500 | C3S—H3SA | 0.9500 |
C31—C36 | 1.375 (6) | C4S—C5S | 1.395 (10) |
C31—C32 | 1.413 (6) | C4S—H4SA | 0.9500 |
C32—C33 | 1.373 (7) | C5S—C6S | 1.358 (10) |
C32—H32A | 0.9500 | C5S—H5SA | 0.9500 |
C33—C34 | 1.390 (7) | C6S—H6SA | 0.9500 |
C33—H33A | 0.9500 | ||
H1RU—Ru1—N1 | 83.6 (17) | C33—C34—H34A | 120.2 |
H1RU—Ru1—N2 | 88.3 (18) | C35—C34—H34A | 120.2 |
N1—Ru1—N2 | 73.71 (13) | C34—C35—C36 | 120.1 (5) |
H1RU—Ru1—P2 | 77.1 (18) | C34—C35—H35A | 120.0 |
N1—Ru1—P2 | 93.60 (10) | C36—C35—H35A | 120.0 |
N2—Ru1—P2 | 161.78 (10) | C31—C36—C35 | 120.7 (4) |
H1RU—Ru1—P1 | 93.3 (17) | C31—C36—H36A | 119.6 |
N1—Ru1—P1 | 173.36 (11) | C35—C36—H36A | 119.6 |
N2—Ru1—P1 | 100.40 (10) | C38—C37—C42 | 119.8 (4) |
P2—Ru1—P1 | 91.39 (4) | C38—C37—P2 | 121.8 (3) |
H1RU—Ru1—Cl1 | 165.3 (17) | C42—C37—P2 | 118.4 (4) |
N1—Ru1—Cl1 | 81.75 (11) | C37—C38—C39 | 120.0 (4) |
N2—Ru1—Cl1 | 87.38 (11) | C37—C38—H38A | 120.0 |
P2—Ru1—Cl1 | 104.00 (5) | C39—C38—H38A | 120.0 |
P1—Ru1—Cl1 | 101.29 (4) | C40—C39—C38 | 119.5 (5) |
C1—P1—C31 | 103.3 (2) | C40—C39—H39A | 120.3 |
C1—P1—C21 | 105.44 (18) | C38—C39—H39A | 120.3 |
C31—P1—C21 | 98.7 (2) | C41—C40—C39 | 120.9 (5) |
C1—P1—Ru1 | 112.21 (14) | C41—C40—H40A | 119.5 |
C31—P1—Ru1 | 120.46 (14) | C39—C40—H40A | 119.5 |
C21—P1—Ru1 | 114.83 (14) | C42—C41—C40 | 119.3 (5) |
C11—P2—C37 | 96.0 (2) | C42—C41—H41A | 120.3 |
C11—P2—C51 | 105.9 (2) | C40—C41—H41A | 120.3 |
C37—P2—C51 | 99.3 (2) | C41—C42—C37 | 120.6 (5) |
C11—P2—Ru1 | 116.93 (15) | C41—C42—H42A | 119.7 |
C37—P2—Ru1 | 129.15 (15) | C37—C42—H42A | 119.7 |
C51—P2—Ru1 | 106.61 (13) | C56—C51—C52 | 117.6 (4) |
C57—O1—C63 | 105.1 (3) | C56—C51—P2 | 122.3 (4) |
C58—N1—Ru1 | 110.4 (3) | C52—C51—P2 | 119.3 (4) |
C58—N1—H1A | 109.6 | C53—C52—C51 | 121.5 (5) |
Ru1—N1—H1A | 109.6 | C53—C52—H52A | 119.2 |
C58—N1—H1B | 109.6 | C51—C52—H52A | 119.2 |
Ru1—N1—H1B | 109.6 | C54—C53—C52 | 120.1 (6) |
H1A—N1—H1B | 108.1 | C54—C53—H53A | 119.9 |
C57—N2—C62 | 105.9 (4) | C52—C53—H53A | 119.9 |
C57—N2—Ru1 | 112.1 (3) | C55—C54—C53 | 120.0 (5) |
C62—N2—Ru1 | 141.8 (3) | C55—C54—H54A | 120.0 |
C10—C1—C2 | 118.5 (4) | C53—C54—H54A | 120.0 |
C10—C1—P1 | 120.1 (3) | C54—C55—C56 | 119.8 (6) |
C2—C1—P1 | 120.5 (3) | C54—C55—H55A | 120.1 |
C3—C2—C1 | 121.6 (4) | C56—C55—H55A | 120.1 |
C3—C2—H2A | 119.2 | C51—C56—C55 | 120.9 (5) |
C1—C2—H2A | 119.2 | C51—C56—H56A | 119.6 |
C2—C3—C4 | 121.1 (4) | C55—C56—H56A | 119.6 |
C2—C3—H3A | 119.4 | N2—C57—O1 | 118.6 (4) |
C4—C3—H3A | 119.4 | N2—C57—C58 | 122.8 (4) |
C9—C4—C5 | 119.9 (4) | O1—C57—C58 | 118.6 (4) |
C9—C4—C3 | 118.1 (4) | N1—C58—C57 | 105.3 (3) |
C5—C4—C3 | 122.0 (4) | N1—C58—C59 | 116.0 (4) |
C6—C5—C4 | 120.6 (5) | C57—C58—C59 | 114.2 (4) |
C6—C5—H5A | 119.7 | N1—C58—H58A | 106.9 |
C4—C5—H5A | 119.7 | C57—C58—H58A | 106.9 |
C5—C6—C7 | 120.1 (4) | C59—C58—H58A | 106.9 |
C5—C6—H6A | 119.9 | C60—C59—C61 | 110.9 (5) |
C7—C6—H6A | 119.9 | C60—C59—C58 | 111.5 (5) |
C8—C7—C6 | 121.0 (5) | C61—C59—C58 | 110.4 (4) |
C8—C7—H7A | 119.5 | C60—C59—H59A | 108.0 |
C6—C7—H7A | 119.5 | C61—C59—H59A | 108.0 |
C7—C8—C9 | 120.3 (4) | C58—C59—H59A | 108.0 |
C7—C8—H8A | 119.9 | C59—C60—H60A | 109.5 |
C9—C8—H8A | 119.9 | C59—C60—H60B | 109.5 |
C4—C9—C8 | 118.1 (4) | H60A—C60—H60B | 109.5 |
C4—C9—C10 | 120.8 (4) | C59—C60—H60C | 109.5 |
C8—C9—C10 | 121.1 (4) | H60A—C60—H60C | 109.5 |
C1—C10—C9 | 119.8 (4) | H60B—C60—H60C | 109.5 |
C1—C10—C20 | 121.5 (4) | C59—C61—H61A | 109.5 |
C9—C10—C20 | 118.5 (3) | C59—C61—H61B | 109.5 |
C20—C11—C12 | 119.3 (4) | H61A—C61—H61B | 109.5 |
C20—C11—P2 | 119.8 (3) | C59—C61—H61C | 109.5 |
C12—C11—P2 | 120.9 (3) | H61A—C61—H61C | 109.5 |
C13—C12—C11 | 120.2 (4) | H61B—C61—H61C | 109.5 |
C13—C12—H12A | 119.9 | N2—C62—C64 | 108.7 (4) |
C11—C12—H12A | 119.9 | N2—C62—C63 | 102.3 (4) |
C12—C13—C14 | 122.2 (5) | C64—C62—C63 | 112.5 (4) |
C12—C13—H13A | 118.9 | N2—C62—H62A | 111.0 |
C14—C13—H13A | 118.9 | C64—C62—H62A | 111.0 |
C13—C14—C15 | 122.9 (5) | C63—C62—H62A | 111.0 |
C13—C14—C19 | 118.2 (4) | O1—C63—C65 | 110.2 (4) |
C15—C14—C19 | 118.9 (4) | O1—C63—C62 | 101.4 (4) |
C16—C15—C14 | 121.7 (5) | C65—C63—C62 | 116.8 (4) |
C16—C15—H15A | 119.1 | O1—C63—H63A | 109.4 |
C14—C15—H15A | 119.1 | C65—C63—H63A | 109.4 |
C15—C16—C17 | 119.5 (5) | C62—C63—H63A | 109.4 |
C15—C16—H16A | 120.3 | C62—C64—H64A | 109.5 |
C17—C16—H16A | 120.3 | C62—C64—H64B | 109.5 |
C18—C17—C16 | 120.7 (4) | H64A—C64—H64B | 109.5 |
C18—C17—H17A | 119.7 | C62—C64—H64C | 109.5 |
C16—C17—H17A | 119.7 | H64A—C64—H64C | 109.5 |
C17—C18—C19 | 121.6 (5) | H64B—C64—H64C | 109.5 |
C17—C18—H18A | 119.2 | C70—C65—C66 | 118.9 (6) |
C19—C18—H18A | 119.2 | C70—C65—C63 | 119.4 (5) |
C18—C19—C20 | 123.4 (4) | C66—C65—C63 | 121.7 (5) |
C18—C19—C14 | 117.6 (4) | C67—C66—C65 | 120.4 (6) |
C20—C19—C14 | 119.0 (4) | C67—C66—H66A | 119.8 |
C11—C20—C19 | 121.0 (4) | C65—C66—H66A | 119.8 |
C11—C20—C10 | 122.5 (4) | C66—C67—C68 | 119.2 (6) |
C19—C20—C10 | 116.5 (3) | C66—C67—H67A | 120.4 |
C22—C21—C26 | 118.5 (4) | C68—C67—H67A | 120.4 |
C22—C21—P1 | 121.7 (3) | C69—C68—C67 | 121.7 (7) |
C26—C21—P1 | 119.4 (4) | C69—C68—H68A | 119.1 |
C23—C22—C21 | 120.6 (4) | C67—C68—H68A | 119.1 |
C23—C22—H22A | 119.7 | C68—C69—C70 | 118.9 (6) |
C21—C22—H22A | 119.7 | C68—C69—H69A | 120.6 |
C24—C23—C22 | 121.0 (5) | C70—C69—H69A | 120.6 |
C24—C23—H23A | 119.5 | C69—C70—C65 | 120.9 (6) |
C22—C23—H23A | 119.5 | C69—C70—H70A | 119.5 |
C23—C24—C25 | 119.5 (4) | C65—C70—H70A | 119.5 |
C23—C24—H24A | 120.2 | C6S—C1S—C2S | 121.3 (6) |
C25—C24—H24A | 120.2 | C6S—C1S—H1SA | 119.3 |
C26—C25—C24 | 119.9 (5) | C2S—C1S—H1SA | 119.3 |
C26—C25—H25A | 120.0 | C3S—C2S—C1S | 118.3 (6) |
C24—C25—H25A | 120.0 | C3S—C2S—H2SA | 120.9 |
C25—C26—C21 | 120.3 (4) | C1S—C2S—H2SA | 120.9 |
C25—C26—H26A | 119.9 | C2S—C3S—C4S | 121.4 (6) |
C21—C26—H26A | 119.9 | C2S—C3S—H3SA | 119.3 |
C36—C31—C32 | 118.7 (4) | C4S—C3S—H3SA | 119.3 |
C36—C31—P1 | 121.1 (3) | C3S—C4S—C5S | 119.6 (6) |
C32—C31—P1 | 119.8 (3) | C3S—C4S—H4SA | 120.2 |
C33—C32—C31 | 120.7 (4) | C5S—C4S—H4SA | 120.2 |
C33—C32—H32A | 119.7 | C6S—C5S—C4S | 118.9 (6) |
C31—C32—H32A | 119.7 | C6S—C5S—H5SA | 120.6 |
C32—C33—C34 | 120.2 (4) | C4S—C5S—H5SA | 120.6 |
C32—C33—H33A | 119.9 | C1S—C6S—C5S | 120.5 (6) |
C34—C33—H33A | 119.9 | C1S—C6S—H6SA | 119.7 |
C33—C34—C35 | 119.6 (5) | C5S—C6S—H6SA | 119.7 |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1B···Cl1 | 0.92 | 2.71 | 3.123 (4) | 109 |
N1—H1A···Cg1 | 0.92 | 2.62 | 3.487 (5) | 157 |
C62—H62A···Cg2 | 1.00 | 2.63 | 2.482 (6) | 143 |
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