Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806041717/ac2050sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806041717/ac20503sup2.hkl |
CCDC reference: 627284
Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 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).
[PtCl2(C14H16)] | F(000) = 848 |
Mr = 450.26 | Dx = 2.479 Mg m−3 |
Monoclinic, P21/c | Cu Kα radiation, λ = 1.54184 Å |
Hall symbol: -P 2ybc | Cell parameters from 25 reflections |
a = 6.6686 (10) Å | θ = 4.7–16.8° |
b = 13.648 (3) Å | µ = 25.58 mm−1 |
c = 13.321 (3) Å | T = 295 K |
β = 95.794 (18)° | Polyhedron, light brown |
V = 1206.2 (4) Å3 | 0.32 × 0.26 × 0.16 mm |
Z = 4 |
Enraf–Nonius CAD-4 diffractometer | Rint = 0.086 |
non–profiled ω/2θ scans | θmax = 70.0°, θmin = 4.7° |
Absorption correction: analytical (see. N.W. Alcock (1970). Cryst. Computing, p271) | h = −8→0 |
Tmin = 0.019, Tmax = 0.141 | k = 0→16 |
2494 measured reflections | l = −16→16 |
2287 independent reflections | 3 standard reflections every 60 min |
2222 reflections with I > 2σ(I) | intensity decay: none |
Refinement on F2 | H-atom parameters constrained |
Least-squares matrix: full | w = 1/[σ2(Fo2) + (0.1018P)2 + 4.3395P] where P = (Fo2 + 2Fc2)/3 |
R[F2 > 2σ(F2)] = 0.056 | (Δ/σ)max < 0.001 |
wR(F2) = 0.146 | Δρmax = 5.65 e Å−3 |
S = 1.20 | Δρmin = −2.33 e Å−3 |
2287 reflections | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
155 parameters | Extinction coefficient: 0.0037 (3) |
0 restraints |
Experimental. 1H NMR (CD2Cl2, 500?MHz): δ = 5.54 (broad s with Pt satellites, 5-, 6-, 12-, 13-H), 3.65 (broad s, 4-, 7-, 11-, 14-H), 2.36 (d, 2-, 9-Hendo), 2.14 (broad s, 1-, 3-, 8-, 10-H), 1.13 (d, 2-, 9-Hexo)p.p.m.; 2 J2endo,2exo = 2 J9endo,9exo = 12.5?Hz, JPt,H = 37?Hz; 13 C NMR (CD2Cl2, 125.7?MHz): δ = 99.0 (C-5, -6, -12, -13), 54.1 (C-4, -7, -11, -14), 39.6 (C-1, -3, -8, -10), 33.3 (C-2, -9)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. |
x | y | z | Uiso*/Ueq | ||
Pt | 0.13680 (4) | 0.08579 (2) | 0.12378 (2) | 0.0272 (3) | |
Cl1 | −0.1517 (3) | 0.01191 (15) | 0.16546 (19) | 0.0451 (5) | |
Cl2 | 0.3173 (3) | −0.05358 (15) | 0.17382 (17) | 0.0418 (5) | |
C6 | −0.0109 (11) | 0.2273 (6) | 0.1275 (6) | 0.0305 (15) | |
H6 | −0.082 | 0.2025 | 0.1785 | 0.037* | |
C7 | 0.1364 (12) | 0.3094 (6) | 0.1488 (6) | 0.0314 (16) | |
H7 | 0.1129 | 0.3392 | 0.2135 | 0.038* | |
C1 | 0.4121 (13) | 0.3074 (6) | −0.0379 (7) | 0.0380 (18) | |
H1 | 0.539 | 0.3042 | −0.069 | 0.046* | |
C11 | 0.3637 (12) | 0.2812 (6) | 0.1524 (6) | 0.0315 (16) | |
H11 | 0.4299 | 0.3001 | 0.2186 | 0.038* | |
C5 | −0.0399 (12) | 0.1885 (6) | 0.0297 (7) | 0.0328 (17) | |
H5 | −0.1262 | 0.1357 | 0.015 | 0.039* | |
C9 | 0.3123 (13) | 0.4402 (6) | 0.0822 (8) | 0.0397 (19) | |
H9A | 0.3356 | 0.469 | 0.1489 | 0.048* | |
H9B | 0.3297 | 0.4895 | 0.0313 | 0.048* | |
C10 | 0.4461 (12) | 0.3492 (6) | 0.0706 (6) | 0.0336 (17) | |
H10 | 0.5887 | 0.3648 | 0.0887 | 0.04* | |
C3 | 0.0721 (13) | 0.3481 (6) | −0.0448 (7) | 0.0375 (18) | |
H3 | −0.0506 | 0.3754 | −0.0809 | 0.045* | |
C12 | 0.4079 (11) | 0.1738 (6) | 0.1356 (6) | 0.0297 (15) | |
H12 | 0.4564 | 0.1337 | 0.1891 | 0.036* | |
C14 | 0.3020 (13) | 0.2066 (6) | −0.0447 (6) | 0.0337 (16) | |
H14 | 0.3261 | 0.1761 | −0.109 | 0.04* | |
C13 | 0.3743 (12) | 0.1369 (6) | 0.0389 (7) | 0.0326 (16) | |
H13 | 0.3957 | 0.071 | 0.0258 | 0.039* | |
C8 | 0.1069 (13) | 0.3899 (6) | 0.0651 (7) | 0.0327 (16) | |
H8 | −0.0014 | 0.4352 | 0.0785 | 0.039* | |
C4 | 0.0707 (13) | 0.2338 (6) | −0.0496 (6) | 0.0351 (17) | |
H4 | 0.0054 | 0.2138 | −0.1157 | 0.042* | |
C2 | 0.2567 (14) | 0.3697 (6) | −0.1012 (6) | 0.0386 (18) | |
H2A | 0.2374 | 0.3479 | −0.1708 | 0.046* | |
H2B | 0.2919 | 0.4387 | −0.0989 | 0.046* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Pt | 0.0286 (3) | 0.0239 (3) | 0.0286 (3) | −0.00016 (9) | 0.00041 (17) | 0.00155 (9) |
Cl1 | 0.0385 (11) | 0.0361 (10) | 0.0613 (14) | −0.0060 (8) | 0.0084 (9) | 0.0113 (9) |
Cl2 | 0.0444 (11) | 0.0295 (10) | 0.0492 (12) | 0.0061 (8) | −0.0059 (9) | 0.0062 (8) |
C6 | 0.027 (4) | 0.029 (4) | 0.035 (4) | 0.003 (3) | 0.007 (3) | 0.003 (3) |
C7 | 0.040 (4) | 0.028 (4) | 0.026 (3) | −0.002 (3) | 0.007 (3) | 0.000 (3) |
C1 | 0.038 (4) | 0.036 (4) | 0.042 (5) | −0.003 (3) | 0.010 (3) | 0.007 (3) |
C11 | 0.036 (4) | 0.028 (4) | 0.029 (4) | −0.004 (3) | −0.002 (3) | 0.003 (3) |
C5 | 0.030 (4) | 0.030 (4) | 0.036 (4) | 0.003 (3) | −0.007 (3) | 0.006 (3) |
C9 | 0.042 (5) | 0.024 (4) | 0.053 (5) | −0.001 (3) | 0.002 (4) | 0.001 (4) |
C10 | 0.037 (4) | 0.024 (4) | 0.042 (4) | −0.007 (3) | 0.008 (3) | 0.002 (3) |
C3 | 0.039 (4) | 0.031 (4) | 0.041 (5) | 0.001 (3) | −0.003 (3) | 0.007 (3) |
C12 | 0.028 (3) | 0.028 (4) | 0.033 (4) | −0.001 (3) | 0.000 (3) | 0.009 (3) |
C14 | 0.043 (4) | 0.029 (4) | 0.029 (4) | −0.002 (3) | 0.007 (3) | 0.001 (3) |
C13 | 0.031 (4) | 0.026 (3) | 0.043 (4) | 0.003 (3) | 0.014 (3) | 0.003 (3) |
C8 | 0.038 (4) | 0.025 (3) | 0.037 (4) | 0.005 (3) | 0.007 (3) | 0.005 (3) |
C4 | 0.046 (5) | 0.034 (4) | 0.024 (4) | −0.001 (3) | −0.007 (3) | 0.000 (3) |
C2 | 0.054 (5) | 0.033 (4) | 0.029 (4) | −0.009 (4) | 0.002 (3) | 0.005 (3) |
Pt—C5 | 2.151 (8) | C5—H5 | 0.93 |
Pt—C13 | 2.153 (7) | C9—C8 | 1.528 (12) |
Pt—C12 | 2.163 (7) | C9—C10 | 1.546 (12) |
Pt—C6 | 2.171 (7) | C9—H9A | 0.97 |
Pt—Cl1 | 2.290 (2) | C9—H9B | 0.97 |
Pt—Cl2 | 2.3129 (19) | C10—H10 | 0.98 |
C6—C5 | 1.402 (12) | C3—C2 | 1.534 (13) |
C6—C7 | 1.498 (11) | C3—C4 | 1.562 (11) |
C6—H6 | 0.93 | C3—C8 | 1.567 (12) |
C7—C11 | 1.560 (11) | C3—H3 | 0.98 |
C7—C8 | 1.562 (11) | C12—C13 | 1.380 (12) |
C7—H7 | 0.98 | C12—H12 | 0.93 |
C1—C2 | 1.527 (12) | C14—C13 | 1.507 (11) |
C1—C10 | 1.550 (12) | C14—C4 | 1.581 (12) |
C1—C14 | 1.557 (11) | C14—H14 | 0.98 |
C1—H1 | 0.98 | C13—H13 | 0.93 |
C11—C12 | 1.516 (11) | C8—H8 | 0.98 |
C11—C10 | 1.572 (11) | C4—H4 | 0.98 |
C11—H11 | 0.98 | C2—H2A | 0.97 |
C5—C4 | 1.484 (12) | C2—H2B | 0.97 |
C5—Pt—C13 | 82.7 (3) | H9A—C9—H9B | 109.8 |
C5—Pt—C12 | 94.9 (3) | C9—C10—C1 | 110.9 (7) |
C13—Pt—C12 | 37.3 (3) | C9—C10—C11 | 99.2 (7) |
C5—Pt—C6 | 37.8 (3) | C1—C10—C11 | 113.7 (6) |
C13—Pt—C6 | 94.8 (3) | C9—C10—H10 | 110.9 |
C12—Pt—C6 | 83.2 (3) | C1—C10—H10 | 110.9 |
C5—Pt—Cl1 | 90.2 (2) | C11—C10—H10 | 110.9 |
C13—Pt—Cl1 | 162.0 (3) | C2—C3—C4 | 100.0 (7) |
C12—Pt—Cl1 | 160.7 (2) | C2—C3—C8 | 109.7 (7) |
C6—Pt—Cl1 | 89.5 (2) | C4—C3—C8 | 113.7 (7) |
C5—Pt—Cl2 | 160.5 (2) | C2—C3—H3 | 111 |
C13—Pt—Cl2 | 91.6 (2) | C4—C3—H3 | 111 |
C12—Pt—Cl2 | 91.6 (2) | C8—C3—H3 | 111 |
C6—Pt—Cl2 | 161.7 (2) | C13—C12—C11 | 118.4 (7) |
Cl1—Pt—Cl2 | 89.63 (8) | C13—C12—Pt | 71.0 (4) |
C5—C6—C7 | 119.0 (7) | C11—C12—Pt | 112.0 (5) |
C5—C6—Pt | 70.3 (4) | C13—C12—H12 | 120.8 |
C7—C6—Pt | 112.3 (5) | C11—C12—H12 | 120.8 |
C5—C6—H6 | 120.5 | Pt—C12—H12 | 87.3 |
C7—C6—H6 | 120.5 | C13—C14—C1 | 113.7 (7) |
Pt—C6—H6 | 87.6 | C13—C14—C4 | 114.6 (6) |
C6—C7—C11 | 115.9 (6) | C1—C14—C4 | 104.3 (6) |
C6—C7—C8 | 111.0 (7) | C13—C14—H14 | 108 |
C11—C7—C8 | 104.4 (6) | C1—C14—H14 | 108 |
C6—C7—H7 | 108.4 | C4—C14—H14 | 108 |
C11—C7—H7 | 108.4 | C12—C13—C14 | 118.0 (7) |
C8—C7—H7 | 108.4 | C12—C13—Pt | 71.7 (4) |
C2—C1—C10 | 109.8 (7) | C14—C13—Pt | 113.3 (5) |
C2—C1—C14 | 99.8 (7) | C12—C13—H13 | 121 |
C10—C1—C14 | 113.8 (6) | C14—C13—H13 | 121 |
C2—C1—H1 | 111 | Pt—C13—H13 | 85.4 |
C10—C1—H1 | 111 | C9—C8—C7 | 99.4 (7) |
C14—C1—H1 | 111 | C9—C8—C3 | 110.4 (7) |
C12—C11—C7 | 115.9 (6) | C7—C8—C3 | 114.0 (7) |
C12—C11—C10 | 112.4 (7) | C9—C8—H8 | 110.8 |
C7—C11—C10 | 103.8 (6) | C7—C8—H8 | 110.8 |
C12—C11—H11 | 108.1 | C3—C8—H8 | 110.8 |
C7—C11—H11 | 108.1 | C5—C4—C3 | 112.8 (7) |
C10—C11—H11 | 108.1 | C5—C4—C14 | 115.2 (6) |
C6—C5—C4 | 118.2 (7) | C3—C4—C14 | 103.4 (7) |
C6—C5—Pt | 71.9 (4) | C5—C4—H4 | 108.4 |
C4—C5—Pt | 113.8 (5) | C3—C4—H4 | 108.4 |
C6—C5—H5 | 120.9 | C14—C4—H4 | 108.4 |
C4—C5—H5 | 120.9 | C1—C2—C3 | 99.0 (6) |
Pt—C5—H5 | 84.8 | C1—C2—H2A | 112 |
C8—C9—C10 | 98.2 (7) | C3—C2—H2A | 112 |
C8—C9—H9A | 112.1 | C1—C2—H2B | 112 |
C10—C9—H9A | 112.1 | C3—C2—H2B | 112 |
C8—C9—H9B | 112.1 | H2A—C2—H2B | 109.7 |
C10—C9—H9B | 112.1 |
Structure | C═C, Å | ω, ° |
Present Study | 1.402 (12) | 121.6 (4) |
1.380 (12) | ||
Free Ligand | 1.321 (3) | 122.7 |
of Present Studya | 1.316 (3) | |
Lee et al.b | 1.355 | 126.6 |
1.406 | ||
Lee et al.c | 1.297 | 126.1 |
1.384 |
Notes: (a) Bau et al. (2005); (b) Lee et al. (1991), S-(Homohypostrophene)neopentyl(endo-2-norbornyl)platinum(II); (c) Lee et al. (1991), R-(Homohypostrophene)neopentyl(exo-2-norbornyl)platinum(II). |