Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802012096/cf6194sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536802012096/cf61941sup2.hkl |
CCDC reference: 193707
Key indicators
- Single-crystal X-ray study
- T = 183 K
- Mean (C-C) = 0.004 Å
- R factor = 0.031
- wR factor = 0.080
- Data-to-parameter ratio = 19.2
checkCIF results
No syntax errors found ADDSYM reports no extra symmetry
Alert Level B:
ABSTM_02 Alert B The ratio of Tmax/Tmin expected RT(exp) is > 1.20 Absorption corrections should be applied. Tmin and Tmax expected: 0.686 0.851 RT(exp) = 1.241
0 Alert Level A = Potentially serious problem
1 Alert Level B = Potential problem
0 Alert Level C = Please check
Data collection: P3 (Nicolet, 1987); cell refinement: P3; data reduction: XDISK (Nicolet, 1987); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP (Siemens, 1994); software used to prepare material for publication: SHELXL97.
[Ru(C10H15)(C14H15)] | Z = 2 |
Mr = 419.55 | F(000) = 436 |
Triclinic, P1 | Dx = 1.423 Mg m−3 |
a = 8.651 (2) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 9.949 (2) Å | Cell parameters from 50 reflections |
c = 11.575 (3) Å | θ = 10–11.5° |
α = 82.82 (2)° | µ = 0.80 mm−1 |
β = 82.09 (2)° | T = 183 K |
γ = 88.88 (2)° | Tablet, yellow |
V = 979.0 (4) Å3 | 0.5 × 0.4 × 0.2 mm |
Nicolet R3 diffractometer | Rint = 0.011 |
Radiation source: fine-focus sealed tube | θmax = 27.5°, θmin = 3.1° |
Graphite monochromator | h = −11→4 |
ω scans | k = −12→12 |
4763 measured reflections | l = −14→15 |
4477 independent reflections | 3 standard reflections every 147 reflections |
4120 reflections with I > 2σ(I) | intensity decay: none |
Refinement on F2 | Primary atom site location: Patterson |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.031 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.080 | H-atom parameters constrained |
S = 1.05 | w = 1/[σ2(Fo2) + (0.0512P)2 + 0.7774P] where P = (Fo2 + 2Fc2)/3 |
4477 reflections | (Δ/σ)max = 0.008 |
233 parameters | Δρmax = 3.08 e Å−3 |
0 restraints | Δρmin = −0.44 e Å−3 |
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. Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane) 0.4671 (0.0056) x + 7.1725 (0.0049) y - 6.7659 (0.0057) z = 2.0808 (0.0026) * -0.0122 (0.0018) C1 * 0.0307 (0.0019) C2 * -0.0053 (0.0019) C3 * -0.0075 (0.0020) C3A * -0.0193 (0.0018) C4 * 0.0178 (0.0018) C4A * 0.0174 (0.0018) C7A * -0.0133 (0.0018) C8 * -0.0083 (0.0020) C8A -1.8394 (0.0012) Ru Rms deviation of fitted atoms = 0.0164 - 0.5633 (0.0099) x - 7.2575 (0.0082) y + 6.6256 (0.0111) z = 1.4885 (0.0042) Angle to previous plane (with approximate e.s.d.) = 0.97 (0.14) * 0.0021 (0.0014) C11 * -0.0006 (0.0014) C12 * -0.0012 (0.0014) C13 * 0.0025 (0.0014) C14 * -0.0029 (0.0014) C15 - 1.7883 (0.0012) Ru Rms deviation of fitted atoms = 0.0020 |
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 | 0.14892 (2) | 0.203674 (16) | 0.190517 (14) | 0.01901 (7) | |
C1 | 0.0468 (3) | 0.3889 (2) | 0.1098 (2) | 0.0271 (5) | |
H1 | −0.0588 | 0.4132 | 0.1322 | 0.033* | |
C2 | 0.1016 (3) | 0.3069 (2) | 0.0203 (2) | 0.0296 (5) | |
H2 | 0.0389 | 0.2705 | −0.0294 | 0.036* | |
C3 | 0.2651 (3) | 0.2886 (2) | 0.0174 (2) | 0.0273 (5) | |
H3 | 0.3297 | 0.2349 | −0.0321 | 0.033* | |
C3A | 0.3163 (3) | 0.3655 (2) | 0.10290 (19) | 0.0215 (4) | |
C4 | 0.4674 (3) | 0.3851 (2) | 0.1358 (2) | 0.0231 (4) | |
C4A | 0.4735 (3) | 0.4689 (2) | 0.2196 (2) | 0.0234 (4) | |
C5 | 0.6168 (3) | 0.5109 (3) | 0.2682 (3) | 0.0333 (6) | |
H5A | 0.7045 | 0.5329 | 0.2045 | 0.040* | |
H5B | 0.6499 | 0.4384 | 0.3264 | 0.040* | |
C6 | 0.5619 (4) | 0.6369 (3) | 0.3264 (3) | 0.0390 (6) | |
H6A | 0.5808 | 0.7199 | 0.2698 | 0.047* | |
H6B | 0.6174 | 0.6448 | 0.3946 | 0.047* | |
C7 | 0.3864 (3) | 0.6154 (3) | 0.3661 (2) | 0.0333 (6) | |
H7A | 0.3668 | 0.5661 | 0.4465 | 0.040* | |
H7B | 0.3299 | 0.7029 | 0.3645 | 0.040* | |
C7A | 0.3376 (3) | 0.5315 (2) | 0.2767 (2) | 0.0236 (4) | |
C8 | 0.1915 (3) | 0.5123 (2) | 0.2507 (2) | 0.0235 (4) | |
C8A | 0.1790 (3) | 0.4284 (2) | 0.1602 (2) | 0.0217 (4) | |
C9 | 0.0462 (3) | 0.5729 (3) | 0.3121 (3) | 0.0344 (6) | |
H9A | 0.0757 | 0.6346 | 0.3651 | 0.041* | |
H9B | −0.0195 | 0.5003 | 0.3576 | 0.041* | |
H9C | −0.0118 | 0.6231 | 0.2536 | 0.041* | |
C10 | 0.6067 (3) | 0.3161 (3) | 0.0760 (2) | 0.0318 (5) | |
H10A | 0.6364 | 0.3634 | −0.0033 | 0.038* | |
H10B | 0.5805 | 0.2219 | 0.0707 | 0.038* | |
H10C | 0.6941 | 0.3181 | 0.1214 | 0.038* | |
C11 | 0.2593 (3) | 0.0501 (2) | 0.3019 (2) | 0.0232 (4) | |
C12 | 0.1753 (3) | −0.0136 (2) | 0.2246 (2) | 0.0228 (4) | |
C13 | 0.0128 (3) | 0.0217 (2) | 0.2493 (2) | 0.0236 (4) | |
C14 | −0.0031 (3) | 0.1068 (2) | 0.3418 (2) | 0.0250 (5) | |
C15 | 0.1485 (3) | 0.1250 (2) | 0.3738 (2) | 0.0253 (5) | |
C16 | 0.4301 (3) | 0.0371 (3) | 0.3113 (3) | 0.0365 (6) | |
H16A | 0.4460 | −0.0314 | 0.3772 | 0.044* | |
H16B | 0.4705 | 0.1245 | 0.3245 | 0.044* | |
H16C | 0.4856 | 0.0097 | 0.2382 | 0.044* | |
C17 | 0.2442 (3) | −0.1052 (3) | 0.1373 (2) | 0.0316 (5) | |
H17A | 0.3544 | −0.0826 | 0.1123 | 0.038* | |
H17B | 0.1878 | −0.0933 | 0.0689 | 0.038* | |
H17C | 0.2353 | −0.1996 | 0.1738 | 0.038* | |
C18 | −0.1168 (3) | −0.0295 (3) | 0.1929 (3) | 0.0345 (6) | |
H18A | −0.1549 | −0.1160 | 0.2364 | 0.041* | |
H18B | −0.0780 | −0.0424 | 0.1114 | 0.041* | |
H18C | −0.2023 | 0.0367 | 0.1940 | 0.041* | |
C19 | −0.1529 (3) | 0.1625 (3) | 0.3989 (3) | 0.0381 (6) | |
H19A | −0.1942 | 0.1002 | 0.4682 | 0.046* | |
H19B | −0.2289 | 0.1728 | 0.3430 | 0.046* | |
H19C | −0.1333 | 0.2510 | 0.4229 | 0.046* | |
C20 | 0.1872 (4) | 0.2056 (3) | 0.4672 (2) | 0.0413 (7) | |
H20A | 0.1118 | 0.2797 | 0.4756 | 0.050* | |
H20B | 0.2925 | 0.2430 | 0.4449 | 0.050* | |
H20C | 0.1825 | 0.1466 | 0.5420 | 0.050* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Ru | 0.02157 (10) | 0.01568 (10) | 0.01959 (10) | 0.00024 (6) | −0.00179 (7) | −0.00265 (6) |
C1 | 0.0266 (11) | 0.0203 (11) | 0.0341 (13) | 0.0014 (9) | −0.0079 (10) | 0.0018 (9) |
C2 | 0.0420 (14) | 0.0235 (11) | 0.0248 (11) | −0.0053 (10) | −0.0125 (10) | 0.0010 (9) |
C3 | 0.0365 (13) | 0.0226 (11) | 0.0216 (11) | −0.0020 (10) | 0.0006 (9) | −0.0030 (9) |
C3A | 0.0255 (11) | 0.0162 (10) | 0.0211 (10) | −0.0007 (8) | 0.0019 (8) | −0.0018 (8) |
C4 | 0.0234 (11) | 0.0175 (10) | 0.0264 (11) | 0.0004 (8) | 0.0018 (9) | −0.0014 (8) |
C4A | 0.0225 (11) | 0.0201 (10) | 0.0269 (11) | −0.0008 (8) | −0.0027 (9) | −0.0013 (8) |
C5 | 0.0284 (12) | 0.0324 (13) | 0.0411 (15) | 0.0008 (10) | −0.0098 (11) | −0.0066 (11) |
C6 | 0.0427 (16) | 0.0370 (15) | 0.0414 (15) | −0.0072 (12) | −0.0133 (12) | −0.0113 (12) |
C7 | 0.0418 (15) | 0.0292 (13) | 0.0307 (13) | −0.0001 (11) | −0.0057 (11) | −0.0103 (10) |
C7A | 0.0291 (12) | 0.0191 (10) | 0.0221 (10) | 0.0006 (9) | −0.0007 (9) | −0.0036 (8) |
C8 | 0.0256 (11) | 0.0165 (10) | 0.0266 (11) | 0.0022 (8) | 0.0023 (9) | −0.0026 (8) |
C8A | 0.0234 (11) | 0.0151 (10) | 0.0252 (11) | 0.0008 (8) | −0.0010 (8) | 0.0006 (8) |
C9 | 0.0290 (13) | 0.0304 (13) | 0.0423 (15) | 0.0061 (10) | 0.0064 (11) | −0.0119 (11) |
C10 | 0.0256 (12) | 0.0273 (12) | 0.0404 (14) | 0.0025 (9) | 0.0057 (10) | −0.0075 (10) |
C11 | 0.0247 (11) | 0.0192 (10) | 0.0247 (11) | 0.0021 (8) | −0.0038 (9) | 0.0014 (8) |
C12 | 0.0299 (12) | 0.0155 (10) | 0.0221 (10) | 0.0019 (8) | −0.0013 (9) | −0.0018 (8) |
C13 | 0.0245 (11) | 0.0170 (10) | 0.0280 (11) | −0.0039 (8) | −0.0027 (9) | 0.0016 (8) |
C14 | 0.0268 (11) | 0.0199 (10) | 0.0251 (11) | 0.0012 (9) | 0.0040 (9) | 0.0006 (9) |
C15 | 0.0346 (13) | 0.0189 (10) | 0.0218 (11) | −0.0003 (9) | −0.0028 (9) | −0.0005 (8) |
C16 | 0.0281 (13) | 0.0360 (14) | 0.0450 (16) | 0.0005 (11) | −0.0112 (11) | 0.0040 (12) |
C17 | 0.0406 (14) | 0.0219 (11) | 0.0319 (13) | 0.0044 (10) | 0.0004 (11) | −0.0086 (10) |
C18 | 0.0319 (13) | 0.0325 (13) | 0.0402 (15) | −0.0074 (11) | −0.0106 (11) | −0.0010 (11) |
C19 | 0.0350 (14) | 0.0313 (13) | 0.0418 (15) | 0.0068 (11) | 0.0123 (12) | −0.0007 (11) |
C20 | 0.068 (2) | 0.0313 (14) | 0.0266 (13) | −0.0039 (13) | −0.0088 (13) | −0.0095 (11) |
Ru—C12 | 2.162 (2) | C8—C8A | 1.434 (3) |
Ru—C13 | 2.164 (2) | C8—C9 | 1.510 (3) |
Ru—C15 | 2.167 (2) | C9—H9A | 0.980 |
Ru—C11 | 2.167 (2) | C9—H9B | 0.980 |
Ru—C14 | 2.172 (2) | C9—H9C | 0.980 |
Ru—C1 | 2.187 (2) | C10—H10A | 0.980 |
Ru—C3 | 2.189 (2) | C10—H10B | 0.980 |
Ru—C2 | 2.192 (2) | C10—H10C | 0.980 |
Ru—C8A | 2.234 (2) | C11—C12 | 1.439 (3) |
Ru—C3A | 2.235 (2) | C11—C15 | 1.440 (3) |
C1—C2 | 1.422 (4) | C11—C16 | 1.499 (3) |
C1—C8A | 1.436 (3) | C12—C13 | 1.441 (3) |
C1—H1 | 0.950 | C12—C17 | 1.500 (3) |
C2—C3 | 1.419 (4) | C13—C14 | 1.436 (3) |
C2—H2 | 0.950 | C13—C18 | 1.500 (3) |
C3—C3A | 1.444 (3) | C14—C15 | 1.431 (4) |
C3—H3 | 0.950 | C14—C19 | 1.501 (3) |
C3A—C4 | 1.435 (3) | C15—C20 | 1.500 (3) |
C3A—C8A | 1.450 (3) | C16—H16A | 0.980 |
C4—C4A | 1.362 (3) | C16—H16B | 0.980 |
C4—C10 | 1.503 (3) | C16—H16C | 0.980 |
C4A—C7A | 1.438 (3) | C17—H17A | 0.980 |
C4A—C5 | 1.516 (3) | C17—H17B | 0.980 |
C5—C6 | 1.533 (4) | C17—H17C | 0.980 |
C5—H5A | 0.990 | C18—H18A | 0.980 |
C5—H5B | 0.990 | C18—H18B | 0.980 |
C6—C7 | 1.536 (4) | C18—H18C | 0.980 |
C6—H6A | 0.990 | C19—H19A | 0.980 |
C6—H6B | 0.990 | C19—H19B | 0.980 |
C7—C7A | 1.516 (3) | C19—H19C | 0.980 |
C7—H7A | 0.990 | C20—H20A | 0.980 |
C7—H7B | 0.990 | C20—H20B | 0.980 |
C7A—C8 | 1.361 (3) | C20—H20C | 0.980 |
C12—Ru—C13 | 38.92 (9) | C6—C7—H7A | 111.1 |
C12—Ru—C15 | 65.01 (9) | C7A—C7—H7B | 111.1 |
C13—Ru—C15 | 64.85 (9) | C6—C7—H7B | 111.1 |
C12—Ru—C11 | 38.82 (9) | H7A—C7—H7B | 109.0 |
C13—Ru—C11 | 65.03 (9) | C8—C7A—C4A | 122.5 (2) |
C15—Ru—C11 | 38.80 (9) | C8—C7A—C7 | 128.4 (2) |
C12—Ru—C14 | 64.95 (9) | C4A—C7A—C7 | 109.1 (2) |
C13—Ru—C14 | 38.70 (9) | C7A—C8—C8A | 116.7 (2) |
C15—Ru—C14 | 38.52 (9) | C7A—C8—C9 | 123.6 (2) |
C11—Ru—C14 | 64.81 (9) | C8A—C8—C9 | 119.8 (2) |
C12—Ru—C1 | 153.81 (10) | C8—C8A—C1 | 131.7 (2) |
C13—Ru—C1 | 121.99 (9) | C8—C8A—C3A | 120.6 (2) |
C15—Ru—C1 | 130.62 (10) | C1—C8A—C3A | 107.7 (2) |
C11—Ru—C1 | 166.40 (9) | C8—C8A—Ru | 124.68 (16) |
C14—Ru—C1 | 112.40 (9) | C1—C8A—Ru | 69.26 (13) |
C12—Ru—C3 | 113.01 (9) | C3A—C8A—Ru | 71.11 (12) |
C13—Ru—C3 | 132.28 (9) | C8—C9—H9A | 109.5 |
C15—Ru—C3 | 152.70 (10) | C8—C9—H9B | 109.5 |
C11—Ru—C3 | 121.72 (9) | H9A—C9—H9B | 109.5 |
C14—Ru—C3 | 168.12 (10) | C8—C9—H9C | 109.5 |
C1—Ru—C3 | 63.76 (10) | H9A—C9—H9C | 109.5 |
C12—Ru—C2 | 122.86 (9) | H9B—C9—H9C | 109.5 |
C13—Ru—C2 | 113.80 (9) | C4—C10—H10A | 109.5 |
C15—Ru—C2 | 167.06 (10) | C4—C10—H10B | 109.5 |
C11—Ru—C2 | 153.72 (10) | H10A—C10—H10B | 109.5 |
C14—Ru—C2 | 132.24 (10) | C4—C10—H10C | 109.5 |
C1—Ru—C2 | 37.90 (10) | H10A—C10—H10C | 109.5 |
C3—Ru—C2 | 37.81 (10) | H10B—C10—H10C | 109.5 |
C12—Ru—C8A | 166.97 (9) | C12—C11—C15 | 107.8 (2) |
C13—Ru—C8A | 152.88 (9) | C12—C11—C16 | 126.8 (2) |
C15—Ru—C8A | 111.77 (9) | C15—C11—C16 | 125.3 (2) |
C11—Ru—C8A | 130.71 (9) | C12—C11—Ru | 70.38 (13) |
C14—Ru—C8A | 121.22 (9) | C15—C11—Ru | 70.59 (13) |
C1—Ru—C8A | 37.88 (9) | C16—C11—Ru | 126.59 (17) |
C3—Ru—C8A | 63.49 (9) | C11—C12—C13 | 107.9 (2) |
C2—Ru—C8A | 63.01 (9) | C11—C12—C17 | 125.9 (2) |
C12—Ru—C3A | 131.53 (9) | C13—C12—C17 | 126.2 (2) |
C13—Ru—C3A | 168.06 (9) | C11—C12—Ru | 70.81 (13) |
C15—Ru—C3A | 120.93 (9) | C13—C12—Ru | 70.63 (13) |
C11—Ru—C3A | 112.09 (9) | C17—C12—Ru | 126.04 (17) |
C14—Ru—C3A | 152.16 (9) | C14—C13—C12 | 107.9 (2) |
C1—Ru—C3A | 63.57 (9) | C14—C13—C18 | 126.5 (2) |
C3—Ru—C3A | 38.06 (9) | C12—C13—C18 | 125.4 (2) |
C2—Ru—C3A | 63.14 (9) | C14—C13—Ru | 70.95 (13) |
C8A—Ru—C3A | 37.85 (8) | C12—C13—Ru | 70.45 (13) |
C2—C1—C8A | 108.1 (2) | C18—C13—Ru | 127.01 (17) |
C2—C1—Ru | 71.23 (14) | C15—C14—C13 | 108.2 (2) |
C8A—C1—Ru | 72.85 (13) | C15—C14—C19 | 125.6 (2) |
C2—C1—H1 | 126.0 | C13—C14—C19 | 126.2 (2) |
C8A—C1—H1 | 126.0 | C15—C14—Ru | 70.56 (13) |
Ru—C1—H1 | 121.7 | C13—C14—Ru | 70.36 (13) |
C3—C2—C1 | 108.9 (2) | C19—C14—Ru | 126.69 (17) |
C3—C2—Ru | 71.01 (14) | C14—C15—C11 | 108.2 (2) |
C1—C2—Ru | 70.87 (14) | C14—C15—C20 | 126.6 (2) |
C3—C2—H2 | 125.6 | C11—C15—C20 | 125.2 (2) |
C1—C2—H2 | 125.6 | C14—C15—Ru | 70.93 (13) |
Ru—C2—H2 | 124.2 | C11—C15—Ru | 70.61 (13) |
C2—C3—C3A | 108.1 (2) | C20—C15—Ru | 124.98 (18) |
C2—C3—Ru | 71.19 (14) | C11—C16—H16A | 109.5 |
C3A—C3—Ru | 72.70 (13) | C11—C16—H16B | 109.5 |
C2—C3—H3 | 125.9 | H16A—C16—H16B | 109.5 |
C3A—C3—H3 | 125.9 | C11—C16—H16C | 109.5 |
Ru—C3—H3 | 121.9 | H16A—C16—H16C | 109.5 |
C4—C3A—C3 | 132.1 (2) | H16B—C16—H16C | 109.5 |
C4—C3A—C8A | 120.8 (2) | C12—C17—H17A | 109.5 |
C3—C3A—C8A | 107.1 (2) | C12—C17—H17B | 109.5 |
C4—C3A—Ru | 124.42 (16) | H17A—C17—H17B | 109.5 |
C3—C3A—Ru | 69.24 (13) | C12—C17—H17C | 109.5 |
C8A—C3A—Ru | 71.04 (12) | H17A—C17—H17C | 109.5 |
C4A—C4—C3A | 116.2 (2) | H17B—C17—H17C | 109.5 |
C4A—C4—C10 | 124.6 (2) | C13—C18—H18A | 109.5 |
C3A—C4—C10 | 119.3 (2) | C13—C18—H18B | 109.5 |
C4—C4A—C7A | 123.2 (2) | H18A—C18—H18B | 109.5 |
C4—C4A—C5 | 127.5 (2) | C13—C18—H18C | 109.5 |
C7A—C4A—C5 | 109.3 (2) | H18A—C18—H18C | 109.5 |
C4A—C5—C6 | 103.5 (2) | H18B—C18—H18C | 109.5 |
C4A—C5—H5A | 111.1 | C14—C19—H19A | 109.5 |
C6—C5—H5A | 111.1 | C14—C19—H19B | 109.5 |
C4A—C5—H5B | 111.1 | H19A—C19—H19B | 109.5 |
C6—C5—H5B | 111.1 | C14—C19—H19C | 109.5 |
H5A—C5—H5B | 109.0 | H19A—C19—H19C | 109.5 |
C5—C6—C7 | 105.0 (2) | H19B—C19—H19C | 109.5 |
C5—C6—H6A | 110.7 | C15—C20—H20A | 109.5 |
C7—C6—H6A | 110.7 | C15—C20—H20B | 109.5 |
C5—C6—H6B | 110.7 | H20A—C20—H20B | 109.5 |
C7—C6—H6B | 110.7 | C15—C20—H20C | 109.5 |
H6A—C6—H6B | 108.8 | H20A—C20—H20C | 109.5 |
C7A—C7—C6 | 103.4 (2) | H20B—C20—H20C | 109.5 |
C7A—C7—H7A | 111.1 |
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