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
Key indicators
- Single-crystal X-ray study
- T = 295 K
- Mean (C-C) = 0.012 Å
- R factor = 0.056
- wR factor = 0.146
- Data-to-parameter ratio = 14.8
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT410_ALERT_2_B Short Intra H...H Contact H2B .. H9B .. 1.86 Ang.
Alert level C PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 2.42 PLAT342_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 12
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 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 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
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). |