Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536801010170/cf6086sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536801010170/cf6086Isup2.hkl |
CCDC reference: 170748
A solution of n-butyl lithium (1.10 mmol) in hexane was added to a stirred solution of 1,1'-dichloroferrocene (0.29 g, 1.13 mmol) (Kovar et al., 1970) in tetrahydrofuran (25 ml). After 1 h, the solution was cooled to 195 K and [PtIMe3(bipy)] (0.50 g, 0.96 mmol) (Lile & Menzies, 1949) was added. The mixture was allowed to warm slowly to ambient temperature and was then heated under reflux for 3 h. The cooled solution was poured into benzene (50 ml), washed with water (3 x 100 ml), dried over MgSO4 and filtered. Removal of the solvent under vacuum produced a dark-brown oil that was purified by dry-column chromatography on alumina. Hexane eluted 1,1'-dichloroferrocene (0.17 g) and then benzene eluted the title compound which was subsequently crystallized from CH2Cl2/hexane to produce orange–red crystals (yield 0.067 g, 11%)
The atoms of the disordered C5H4Cl rings were refined as part of a rigid group, with C—C bonds of 1.42 Å, C—C—C angles of 108° and with isotropic displacement parameters. Methyl H atoms were located in difference Fourier syntheses while others were placed geometrically. In the refinement, methyl groups were constrained to be rigid rotating groups with C—H distances at 0.96 Å and with Uiso(H) = 1.5Ueq(C). Other H atoms were constrained to ride at 0.93 (bipy and C5H3Cl) or 1.0 Å (disordered C5H4Cl) from their carrier atoms with Uiso(H) = 1.2Ueq(C). The largest ΔF features occur near the Pt positions.
Data collection: local program; cell refinement: local program; data reduction: local program; program(s) used to solve structure: SHELX76 (Sheldrick, 1976); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2001); software used to prepare material for publication: SHELXL97 and PLATON.
[Pt(CH3)3(C10H7Cl2Fe)(C10H8N2)] | F(000) = 2512 |
Mr = 650.28 | Dx = 1.915 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 20.137 (4) Å | Cell parameters from 17 reflections |
b = 10.572 (5) Å | θ = 9.5–21.0° |
c = 21.810 (6) Å | µ = 7.09 mm−1 |
β = 103.71 (1)° | T = 295 K |
V = 4511 (3) Å3 | Plate, orange |
Z = 8 | 0.28 × 0.28 × 0.05 mm |
Stoe Stadi-2 two-circle diffractometer | 5558 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.009 |
Graphite monochromator | θmax = 25.0°, θmin = 2.8° |
ω scans | h = −23→23 |
Absorption correction: ψ scan local program | k = 0→12 |
Tmin = 0.166, Tmax = 0.670 | l = 0→25 |
7797 measured reflections | 3 standard reflections every 360 min |
7797 independent reflections | intensity decay: none |
Refinement on F2 | Primary atom site location: heavy-atom method |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.061 | Hydrogen site location: constr |
wR(F2) = 0.168 | See text |
S = 1.08 | w = 1/[σ2(Fo2) + (0.098P)2] where P = (Fo2 + 2Fc2)/3 |
7797 reflections | (Δ/σ)max = 0.005 |
461 parameters | Δρmax = 2.43 e Å−3 |
200 restraints | Δρmin = −1.13 e Å−3 |
[Pt(CH3)3(C10H7Cl2Fe)(C10H8N2)] | V = 4511 (3) Å3 |
Mr = 650.28 | Z = 8 |
Monoclinic, P21/n | Mo Kα radiation |
a = 20.137 (4) Å | µ = 7.09 mm−1 |
b = 10.572 (5) Å | T = 295 K |
c = 21.810 (6) Å | 0.28 × 0.28 × 0.05 mm |
β = 103.71 (1)° |
Stoe Stadi-2 two-circle diffractometer | 5558 reflections with I > 2σ(I) |
Absorption correction: ψ scan local program | Rint = 0.009 |
Tmin = 0.166, Tmax = 0.670 | 3 standard reflections every 360 min |
7797 measured reflections | intensity decay: none |
7797 independent reflections |
R[F2 > 2σ(F2)] = 0.061 | 200 restraints |
wR(F2) = 0.168 | See text |
S = 1.08 | Δρmax = 2.43 e Å−3 |
7797 reflections | Δρmin = −1.13 e Å−3 |
461 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) | |
Pt | 0.68055 (2) | 0.29385 (4) | 0.007239 (18) | 0.06363 (16) | |
C1M | 0.7152 (6) | 0.3079 (11) | −0.0757 (6) | 0.076 (3) | |
H1M | 0.6929 | 0.3776 | −0.1004 | 0.114* | |
H2M | 0.7049 | 0.2310 | −0.0994 | 0.114* | |
H3M | 0.7637 | 0.3214 | −0.0651 | 0.114* | |
C2M | 0.7829 (6) | 0.3034 (16) | 0.0553 (7) | 0.105 (4) | |
H4M | 0.8062 | 0.3637 | 0.0349 | 0.157* | |
H5M | 0.8037 | 0.2217 | 0.0550 | 0.157* | |
H6M | 0.7861 | 0.3293 | 0.0981 | 0.157* | |
C3M | 0.6970 (7) | 0.1010 (11) | 0.0023 (7) | 0.094 (4) | |
H7M | 0.6678 | 0.0677 | −0.0356 | 0.140* | |
H8M | 0.6870 | 0.0601 | 0.0383 | 0.140* | |
H9M | 0.7439 | 0.0860 | 0.0018 | 0.140* | |
N1 | 0.6590 (4) | 0.4910 (8) | 0.0061 (4) | 0.0655 (18) | |
N2 | 0.5776 (4) | 0.3049 (9) | −0.0520 (4) | 0.071 (2) | |
C11 | 0.6995 (7) | 0.5852 (12) | 0.0345 (6) | 0.081 (3) | |
H11 | 0.7447 | 0.5642 | 0.0529 | 0.097* | |
C12 | 0.6821 (9) | 0.7032 (13) | 0.0391 (6) | 0.099 (4) | |
H12 | 0.7123 | 0.7582 | 0.0651 | 0.119* | |
C13 | 0.6215 (10) | 0.7457 (14) | 0.0067 (9) | 0.113 (5) | |
H13 | 0.6099 | 0.8309 | 0.0061 | 0.136* | |
C14 | 0.5750 (7) | 0.6513 (13) | −0.0274 (8) | 0.104 (4) | |
H14 | 0.5314 | 0.6744 | −0.0499 | 0.125* | |
C15 | 0.5956 (5) | 0.5283 (10) | −0.0263 (5) | 0.070 (2) | |
C16 | 0.5508 (5) | 0.4217 (10) | −0.0593 (5) | 0.070 (2) | |
C17 | 0.4874 (5) | 0.4451 (13) | −0.1019 (5) | 0.077 (3) | |
H17 | 0.4709 | 0.5274 | −0.1081 | 0.092* | |
C18 | 0.4521 (6) | 0.3523 (14) | −0.1325 (6) | 0.088 (3) | |
H18 | 0.4098 | 0.3672 | −0.1599 | 0.106* | |
C19 | 0.4795 (6) | 0.2265 (14) | −0.1233 (5) | 0.086 (3) | |
H19 | 0.4562 | 0.1574 | −0.1445 | 0.104* | |
C20 | 0.5417 (6) | 0.2136 (11) | −0.0817 (5) | 0.074 (3) | |
H20 | 0.5593 | 0.1322 | −0.0743 | 0.089* | |
Fe | 0.67931 (9) | 0.18472 (18) | 0.17953 (8) | 0.0844 (5) | |
C1 | 0.5951 (5) | 0.2037 (10) | 0.1086 (5) | 0.076 (2) | |
C2 | 0.6477 (5) | 0.2792 (9) | 0.0937 (5) | 0.0664 (19) | |
C3 | 0.6676 (5) | 0.3672 (11) | 0.1456 (4) | 0.072 (2) | |
H3 | 0.7012 | 0.4290 | 0.1493 | 0.087* | |
C4 | 0.6275 (6) | 0.3440 (12) | 0.1905 (6) | 0.090 (3) | |
H4 | 0.6304 | 0.3879 | 0.2280 | 0.109* | |
C5 | 0.5817 (6) | 0.2410 (13) | 0.1674 (5) | 0.085 (3) | |
H5 | 0.5497 | 0.2058 | 0.1870 | 0.102* | |
Cl1 | 0.54818 (17) | 0.0851 (3) | 0.06319 (16) | 0.0922 (9) | |
C6 | 0.7074 (7) | 0.0017 (12) | 0.1862 (6) | 0.127 (5)* | |
C7 | 0.7624 (7) | 0.0735 (13) | 0.1740 (6) | 0.135 (6)* | |
C8 | 0.7813 (6) | 0.1654 (12) | 0.2225 (7) | 0.130 (6)* | |
C9 | 0.7379 (8) | 0.1505 (13) | 0.2647 (6) | 0.132 (6)* | |
C10 | 0.6922 (6) | 0.0493 (14) | 0.2423 (7) | 0.141 (6)* | |
H6 | 0.6816 | −0.0756 | 0.1579 | 0.169* | |
H7 | 0.7858 | 0.0604 | 0.1348 | 0.169* | |
H8 | 0.8215 | 0.2346 | 0.2266 | 0.169* | |
H9 | 0.7393 | 0.2063 | 0.3065 | 0.169* | 0.602 (14) |
H10 | 0.6528 | 0.0146 | 0.2640 | 0.169* | 0.398 (14) |
Cl2A | 0.7013 (8) | 0.1820 (16) | 0.3307 (8) | 0.163 (7)* | 0.398 (14) |
Cl2B | 0.6461 (5) | 0.0158 (10) | 0.2913 (5) | 0.159 (4)* | 0.602 (14) |
Pt' | 0.45932 (2) | 0.72749 (6) | 0.34009 (2) | 0.0880 (2) | |
C1M' | 0.5481 (8) | 0.760 (2) | 0.3123 (8) | 0.127 (5) | |
H1M' | 0.5819 | 0.7937 | 0.3470 | 0.190* | |
H2M' | 0.5396 | 0.8191 | 0.2780 | 0.190* | |
H3M' | 0.5644 | 0.6817 | 0.2988 | 0.190* | |
C2M' | 0.4135 (7) | 0.7133 (17) | 0.2456 (6) | 0.106 (4) | |
H4M' | 0.3776 | 0.6515 | 0.2395 | 0.158* | |
H5M' | 0.4468 | 0.6879 | 0.2230 | 0.158* | |
H6M' | 0.3947 | 0.7938 | 0.2302 | 0.158* | |
C3M' | 0.4371 (8) | 0.9110 (15) | 0.3314 (6) | 0.104 (3) | |
H7M' | 0.3958 | 0.9269 | 0.3448 | 0.156* | |
H8M' | 0.4309 | 0.9358 | 0.2881 | 0.156* | |
H9M' | 0.4738 | 0.9589 | 0.3572 | 0.156* | |
N1' | 0.4932 (5) | 0.5349 (11) | 0.3532 (5) | 0.087 (2) | |
N2' | 0.5192 (5) | 0.7267 (10) | 0.4384 (5) | 0.084 (2) | |
C11' | 0.4802 (7) | 0.4382 (19) | 0.3114 (7) | 0.117 (5) | |
H11' | 0.4518 | 0.4536 | 0.2718 | 0.140* | |
C12' | 0.5070 (8) | 0.316 (2) | 0.3243 (9) | 0.134 (6) | |
H12' | 0.4966 | 0.2503 | 0.2954 | 0.161* | |
C13' | 0.5472 (8) | 0.3033 (18) | 0.3792 (9) | 0.124 (5) | |
H13' | 0.5664 | 0.2235 | 0.3884 | 0.149* | |
C14' | 0.5650 (7) | 0.3893 (15) | 0.4248 (7) | 0.097 (3) | |
H14' | 0.5943 | 0.3707 | 0.4636 | 0.116* | |
C15' | 0.5366 (5) | 0.5094 (13) | 0.4103 (5) | 0.076 (2) | |
C16' | 0.5501 (5) | 0.6143 (12) | 0.4535 (5) | 0.076 (2) | |
C17' | 0.5875 (6) | 0.6012 (13) | 0.5173 (6) | 0.086 (3) | |
H17' | 0.6038 | 0.5218 | 0.5320 | 0.103* | |
C18' | 0.5997 (6) | 0.6998 (13) | 0.5566 (6) | 0.091 (4) | |
H18' | 0.6255 | 0.6896 | 0.5977 | 0.110* | |
C19' | 0.5740 (6) | 0.8156 (14) | 0.5359 (6) | 0.093 (4) | |
H19' | 0.5836 | 0.8872 | 0.5612 | 0.112* | |
C20' | 0.5315 (6) | 0.8211 (13) | 0.4730 (6) | 0.089 (3) | |
H20' | 0.5124 | 0.8983 | 0.4577 | 0.106* | |
Fe' | 0.26270 (9) | 0.71797 (17) | 0.33344 (9) | 0.0835 (5) | |
C1' | 0.3353 (5) | 0.7243 (11) | 0.4155 (5) | 0.082 (3) | |
C2' | 0.3684 (5) | 0.6817 (11) | 0.3673 (4) | 0.072 (2) | |
C3' | 0.3281 (5) | 0.5658 (11) | 0.3449 (5) | 0.071 (2) | |
H3' | 0.3352 | 0.5124 | 0.3132 | 0.085* | |
C4' | 0.2781 (6) | 0.5495 (11) | 0.3784 (5) | 0.079 (3) | |
H4' | 0.2465 | 0.4838 | 0.3725 | 0.094* | |
C5' | 0.2827 (6) | 0.6455 (12) | 0.4215 (5) | 0.084 (3) | |
H5' | 0.2550 | 0.6556 | 0.4498 | 0.101* | |
Cl1' | 0.35999 (19) | 0.8612 (3) | 0.46205 (17) | 0.1004 (10) | |
C6' | 0.2352 (7) | 0.8947 (10) | 0.3011 (6) | 0.118 (5)* | |
C7' | 0.2382 (6) | 0.8093 (12) | 0.2516 (6) | 0.132 (6)* | |
C8' | 0.1894 (7) | 0.7121 (10) | 0.2513 (6) | 0.110 (5)* | |
C9' | 0.1563 (7) | 0.7375 (14) | 0.3007 (7) | 0.145 (7)* | |
C10' | 0.1846 (8) | 0.8503 (14) | 0.3314 (6) | 0.157 (7)* | |
H6' | 0.2660 | 0.9786 | 0.3135 | 0.188* | |
H7' | 0.2717 | 0.8169 | 0.2197 | 0.188* | |
H8' | 0.1793 | 0.6329 | 0.2192 | 0.188* | |
H9' | 0.1165 | 0.6809 | 0.3127 | 0.188* | 0.335 (14) |
H10' | 0.1701 | 0.8946 | 0.3710 | 0.188* | 0.665 (14) |
Cl4A | 0.0970 (4) | 0.6382 (9) | 0.3249 (4) | 0.145 (4)* | 0.665 (14) |
Cl4B | 0.1075 (8) | 0.7991 (17) | 0.3418 (8) | 0.146 (7)* | 0.335 (14) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Pt | 0.0565 (2) | 0.0696 (3) | 0.0586 (2) | 0.00896 (18) | 0.00129 (17) | 0.00170 (18) |
C1M | 0.074 (6) | 0.080 (6) | 0.080 (6) | 0.003 (5) | 0.030 (5) | −0.001 (5) |
C2M | 0.045 (5) | 0.156 (11) | 0.099 (8) | 0.019 (6) | −0.010 (5) | 0.018 (8) |
C3M | 0.103 (8) | 0.064 (5) | 0.121 (10) | 0.035 (5) | 0.039 (7) | 0.023 (5) |
N1 | 0.069 (4) | 0.064 (4) | 0.061 (5) | 0.015 (3) | 0.011 (4) | 0.008 (3) |
N2 | 0.048 (4) | 0.080 (4) | 0.073 (5) | 0.010 (3) | −0.007 (3) | 0.012 (4) |
C11 | 0.083 (7) | 0.079 (5) | 0.076 (7) | 0.002 (5) | 0.007 (6) | −0.005 (6) |
C12 | 0.152 (11) | 0.084 (6) | 0.059 (7) | 0.004 (7) | 0.018 (7) | −0.012 (6) |
C13 | 0.142 (11) | 0.071 (6) | 0.136 (13) | 0.032 (6) | 0.053 (9) | −0.008 (7) |
C14 | 0.092 (8) | 0.082 (6) | 0.140 (12) | 0.028 (6) | 0.028 (7) | 0.029 (7) |
C15 | 0.050 (5) | 0.071 (4) | 0.090 (7) | 0.011 (4) | 0.020 (4) | 0.027 (5) |
C16 | 0.053 (5) | 0.077 (5) | 0.074 (6) | 0.021 (4) | 0.006 (4) | 0.020 (5) |
C17 | 0.060 (5) | 0.105 (7) | 0.062 (6) | 0.023 (5) | 0.007 (4) | 0.018 (5) |
C18 | 0.053 (6) | 0.121 (8) | 0.082 (7) | 0.000 (5) | −0.001 (5) | 0.041 (7) |
C19 | 0.078 (7) | 0.111 (7) | 0.059 (6) | −0.011 (6) | −0.006 (5) | 0.005 (6) |
C20 | 0.067 (6) | 0.086 (6) | 0.059 (6) | −0.006 (5) | −0.007 (4) | 0.009 (5) |
Fe | 0.0804 (11) | 0.0912 (11) | 0.0725 (10) | 0.0238 (9) | 0.0001 (8) | 0.0180 (9) |
C1 | 0.065 (5) | 0.085 (6) | 0.075 (5) | 0.011 (4) | 0.010 (4) | 0.015 (4) |
C2 | 0.067 (5) | 0.065 (5) | 0.065 (4) | 0.014 (4) | 0.011 (4) | 0.009 (3) |
C3 | 0.067 (5) | 0.090 (5) | 0.053 (5) | 0.023 (4) | 0.001 (4) | 0.010 (4) |
C4 | 0.112 (9) | 0.089 (7) | 0.074 (6) | 0.019 (5) | 0.030 (6) | 0.006 (5) |
C5 | 0.065 (5) | 0.131 (9) | 0.052 (5) | 0.010 (5) | 0.000 (4) | 0.020 (5) |
Cl1 | 0.095 (2) | 0.0784 (18) | 0.098 (2) | −0.0099 (15) | 0.0115 (17) | 0.0028 (16) |
Pt' | 0.0651 (3) | 0.1270 (5) | 0.0626 (3) | −0.0068 (3) | −0.0037 (2) | 0.0177 (3) |
C1M' | 0.091 (7) | 0.179 (13) | 0.110 (9) | −0.029 (8) | 0.024 (7) | 0.024 (11) |
C2M' | 0.086 (7) | 0.178 (13) | 0.053 (5) | 0.033 (8) | 0.015 (5) | 0.012 (6) |
C3M' | 0.126 (10) | 0.124 (6) | 0.062 (6) | −0.017 (6) | 0.022 (7) | 0.039 (6) |
N1' | 0.060 (5) | 0.122 (5) | 0.072 (5) | 0.002 (5) | 0.002 (4) | −0.008 (4) |
N2' | 0.068 (5) | 0.095 (5) | 0.075 (5) | −0.019 (5) | −0.010 (4) | 0.008 (4) |
C11' | 0.083 (8) | 0.177 (10) | 0.081 (8) | 0.034 (9) | −0.001 (6) | −0.039 (8) |
C12' | 0.092 (10) | 0.176 (11) | 0.118 (10) | 0.048 (10) | −0.007 (8) | −0.074 (11) |
C13' | 0.090 (10) | 0.134 (10) | 0.132 (12) | 0.022 (9) | −0.009 (8) | −0.032 (8) |
C14' | 0.088 (8) | 0.114 (7) | 0.080 (7) | 0.006 (7) | 0.005 (6) | −0.003 (6) |
C15' | 0.033 (4) | 0.114 (6) | 0.072 (6) | 0.001 (5) | −0.004 (4) | 0.001 (5) |
C16' | 0.064 (6) | 0.088 (5) | 0.069 (5) | −0.018 (5) | 0.002 (5) | 0.018 (4) |
C17' | 0.069 (7) | 0.099 (7) | 0.074 (6) | −0.014 (6) | −0.013 (5) | 0.004 (5) |
C18' | 0.056 (6) | 0.101 (7) | 0.092 (7) | −0.007 (6) | −0.029 (6) | 0.005 (6) |
C19' | 0.074 (7) | 0.103 (7) | 0.083 (7) | −0.008 (6) | −0.018 (6) | −0.015 (6) |
C20' | 0.077 (7) | 0.092 (7) | 0.082 (7) | −0.007 (6) | −0.011 (6) | 0.012 (5) |
Fe' | 0.0687 (9) | 0.0794 (10) | 0.0883 (11) | 0.0097 (8) | −0.0097 (8) | 0.0059 (9) |
C1' | 0.054 (5) | 0.098 (7) | 0.084 (6) | 0.007 (4) | −0.004 (3) | −0.023 (6) |
C2' | 0.061 (4) | 0.097 (6) | 0.049 (5) | 0.000 (4) | −0.002 (3) | 0.001 (4) |
C3' | 0.057 (5) | 0.090 (6) | 0.058 (5) | 0.009 (4) | 0.001 (4) | −0.005 (4) |
C4' | 0.096 (7) | 0.083 (5) | 0.057 (6) | −0.013 (5) | 0.017 (5) | 0.008 (4) |
C5' | 0.080 (7) | 0.097 (7) | 0.074 (5) | 0.005 (5) | 0.016 (5) | −0.001 (4) |
Cl1' | 0.103 (2) | 0.088 (2) | 0.099 (2) | 0.0040 (18) | −0.0003 (18) | −0.0217 (18) |
Pt—C1M | 2.092 (11) | Pt'—C1M' | 2.049 (15) |
Pt—C2M | 2.082 (11) | Pt'—C2M' | 2.054 (12) |
Pt—C3M | 2.072 (11) | Pt'—C3M' | 1.990 (16) |
Pt—N1 | 2.128 (8) | Pt'—N1' | 2.145 (12) |
Pt—N2 | 2.170 (8) | Pt'—N2' | 2.196 (10) |
Pt—C2 | 2.146 (11) | Pt'—C2' | 2.110 (11) |
C1M—H1M | 0.96 | C1M'—H1M' | 0.96 |
C1M—H2M | 0.96 | C1M'—H2M' | 0.96 |
C1M—H3M | 0.96 | C1M'—H3M' | 0.96 |
C2M—H4M | 0.96 | C2M'—H4M' | 0.96 |
C2M—H5M | 0.96 | C2M'—H5M' | 0.96 |
C2M—H6M | 0.96 | C2M'—H6M' | 0.96 |
C3M—H7M | 0.96 | C3M'—H7M' | 0.96 |
C3M—H8M | 0.96 | C3M'—H8M' | 0.96 |
C3M—H9M | 0.96 | C3M'—H9M' | 0.96 |
N1—C11 | 1.343 (15) | N1'—C11' | 1.354 (18) |
N1—C15 | 1.363 (12) | N1'—C15' | 1.367 (13) |
N2—C20 | 1.286 (14) | N2'—C20' | 1.241 (17) |
N2—C16 | 1.342 (13) | N2'—C16' | 1.345 (16) |
C11—C12 | 1.306 (18) | C11'—C12' | 1.40 (3) |
C11—H11 | 0.93 | C11'—H11' | 0.93 |
C12—C13 | 1.33 (2) | C12'—C13' | 1.28 (2) |
C12—H12 | 0.93 | C12'—H12' | 0.93 |
C13—C14 | 1.45 (2) | C13'—C14' | 1.33 (2) |
C13—H13 | 0.93 | C13'—H13' | 0.93 |
C14—C15 | 1.363 (17) | C14'—C15' | 1.398 (19) |
C14—H14 | 0.93 | C14'—H14' | 0.93 |
C15—C16 | 1.515 (16) | C15'—C16' | 1.439 (17) |
C16—C17 | 1.411 (14) | C16'—C17' | 1.423 (15) |
C17—C18 | 1.300 (18) | C17'—C18' | 1.334 (18) |
C17—H17 | 0.93 | C17'—H17' | 0.93 |
C18—C19 | 1.44 (2) | C18'—C19' | 1.363 (18) |
C18—H18 | 0.93 | C18'—H18' | 0.93 |
C19—C20 | 1.368 (15) | C19'—C20' | 1.436 (16) |
C19—H19 | 0.93 | C19'—H19' | 0.93 |
C20—H20 | 0.93 | C20'—H20' | 0.93 |
Fe—C1 | 2.017 (10) | Fe'—C1' | 2.026 (10) |
Fe—C2 | 2.085 (9) | Fe'—C2' | 2.117 (10) |
Fe—C3 | 2.059 (11) | Fe'—C3' | 2.056 (10) |
Fe—C4 | 2.025 (11) | Fe'—C4' | 2.021 (10) |
Fe—C5 | 2.011 (11) | Fe'—C5' | 2.018 (11) |
Fe—C6 | 2.011 (14) | Fe'—C6' | 2.027 (13) |
Fe—C7 | 2.072 (13) | Fe'—C7' | 1.986 (13) |
Fe—C8 | 2.055 (13) | Fe'—C8' | 2.034 (13) |
Fe—C9 | 1.983 (14) | Fe'—C9' | 2.102 (14) |
Fe—C10 | 1.955 (14) | Fe'—C10' | 2.098 (14) |
C1—C2 | 1.424 (16) | C1'—C5' | 1.378 (17) |
C1—C5 | 1.429 (17) | C1'—C2' | 1.444 (16) |
C1—Cl1 | 1.732 (13) | C1'—Cl1' | 1.770 (12) |
C2—C3 | 1.448 (15) | C2'—C3' | 1.487 (16) |
C3—C4 | 1.430 (16) | C3'—C4' | 1.387 (15) |
C3—H3 | 0.93 | C3'—H3' | 0.93 |
C4—C5 | 1.438 (19) | C4'—C5' | 1.372 (17) |
C4—H4 | 0.93 | C4'—H4' | 0.93 |
C5—H5 | 0.93 | C5'—H5' | 0.93 |
C6—C7 | 1.42 | C6'—C7' | 1.42 |
C6—C10 | 1.42 | C6'—C10' | 1.42 |
C7—C8 | 1.42 | C7'—C8' | 1.42 |
C7—H7 | 1.08 | C7'—H7' | 1.08 |
C8—C9 | 1.42 | C8'—C9' | 1.42 |
C8—H8 | 1.08 | C8'—H8' | 1.08 |
C9—C10 | 1.42 | C9'—C10' | 1.42 |
C9—Cl2A | 1.798 (19) | C9'—Cl4A | 1.762 (13) |
C9—H9 | 1.08 | C9'—H9' | 1.08 |
C10—Cl2B | 1.614 (14) | C10'—Cl4B | 1.71 (2) |
C10—H10 | 1.08 | C10'—H10' | 1.08 |
C3M—Pt—C2M | 85.6 (6) | C1M'—Pt'—C2M' | 86.0 (6) |
C3M—Pt—C1M | 86.2 (5) | C3M'—Pt'—C2' | 93.4 (5) |
C2M—Pt—C1M | 86.5 (5) | C1M'—Pt'—C2' | 176.3 (7) |
C3M—Pt—N1 | 176.1 (5) | C2M'—Pt'—C2' | 93.0 (5) |
C2M—Pt—N1 | 97.7 (5) | C3M'—Pt'—N1' | 174.5 (5) |
C1M—Pt—N1 | 91.7 (4) | C1M'—Pt'—N1' | 85.7 (6) |
C3M—Pt—C2 | 93.5 (4) | C2M'—Pt'—N1' | 96.8 (6) |
C2M—Pt—C2 | 92.1 (5) | C2'—Pt'—N1' | 90.8 (4) |
C1M—Pt—C2 | 178.5 (4) | C3M'—Pt'—N2' | 98.9 (5) |
N1—Pt—C2 | 88.6 (3) | C1M'—Pt'—N2' | 88.5 (6) |
C3M—Pt—N2 | 99.4 (5) | C2M'—Pt'—N2' | 172.3 (5) |
C2M—Pt—N2 | 171.6 (5) | C2'—Pt'—N2' | 92.1 (4) |
C1M—Pt—N2 | 87.1 (4) | N1'—Pt'—N2' | 77.4 (4) |
N1—Pt—N2 | 77.1 (3) | Pt'—C1M'—H1M' | 109.5 |
C2—Pt—N2 | 94.4 (4) | Pt'—C1M'—H2M' | 109.5 |
Pt—C1M—H1M | 109.5 | H1M'—C1M'—H2M' | 109.5 |
Pt—C1M—H2M | 109.5 | Pt'—C1M'—H3M' | 109.5 |
H1M—C1M—H2M | 109.5 | H1M'—C1M'—H3M' | 109.5 |
Pt—C1M—H3M | 109.5 | H2M'—C1M'—H3M' | 109.5 |
H1M—C1M—H3M | 109.5 | Pt'—C2M'—H4M' | 109.5 |
H2M—C1M—H3M | 109.5 | Pt'—C2M'—H5M' | 109.5 |
Pt—C2M—H4M | 109.5 | H4M'—C2M'—H5M' | 109.5 |
Pt—C2M—H5M | 109.5 | Pt'—C2M'—H6M' | 109.5 |
H4M—C2M—H5M | 109.5 | H4M'—C2M'—H6M' | 109.5 |
Pt—C2M—H6M | 109.5 | H5M'—C2M'—H6M' | 109.5 |
H4M—C2M—H6M | 109.5 | Pt'—C3M'—H7M' | 109.5 |
H5M—C2M—H6M | 109.5 | Pt'—C3M'—H8M' | 109.5 |
Pt—C3M—H7M | 109.5 | H7M'—C3M'—H8M' | 109.5 |
Pt—C3M—H8M | 109.5 | Pt'—C3M'—H9M' | 109.5 |
H7M—C3M—H8M | 109.5 | H7M'—C3M'—H9M' | 109.5 |
Pt—C3M—H9M | 109.5 | H8M'—C3M'—H9M' | 109.5 |
H7M—C3M—H9M | 109.5 | C11'—N1'—C15' | 116.4 (12) |
H8M—C3M—H9M | 109.5 | C11'—N1'—Pt' | 128.5 (9) |
C11—N1—C15 | 114.7 (9) | C15'—N1'—Pt' | 115.0 (8) |
C11—N1—Pt | 128.4 (7) | C20'—N2'—C16' | 123.1 (11) |
C15—N1—Pt | 116.9 (7) | C20'—N2'—Pt' | 125.1 (9) |
C20—N2—C16 | 117.9 (9) | C16'—N2'—Pt' | 111.0 (8) |
C20—N2—Pt | 127.2 (8) | N1'—C11'—C12' | 123.8 (13) |
C16—N2—Pt | 114.9 (7) | N1'—C11'—H11' | 118.1 |
C12—C11—N1 | 126.8 (13) | C12'—C11'—H11' | 118.1 |
C12—C11—H11 | 116.6 | C13'—C12'—C11' | 114.5 (15) |
N1—C11—H11 | 116.6 | C13'—C12'—H12' | 122.8 |
C11—C12—C13 | 120.6 (15) | C11'—C12'—H12' | 122.8 |
C11—C12—H12 | 119.7 | C12'—C13'—C14' | 128.4 (18) |
C13—C12—H12 | 119.7 | C12'—C13'—H13' | 115.8 |
C12—C13—C14 | 116.1 (13) | C14'—C13'—H13' | 115.8 |
C12—C13—H13 | 122.0 | C13'—C14'—C15' | 115.3 (13) |
C14—C13—H13 | 122.0 | C13'—C14'—H14' | 122.3 |
C15—C14—C13 | 119.4 (13) | C15'—C14'—H14' | 122.3 |
C15—C14—H14 | 120.3 | N1'—C15'—C14' | 121.6 (12) |
C13—C14—H14 | 120.3 | N1'—C15'—C16' | 115.2 (11) |
N1—C15—C14 | 122.0 (12) | C14'—C15'—C16' | 123.2 (10) |
N1—C15—C16 | 114.2 (9) | N2'—C16'—C17' | 115.7 (12) |
C14—C15—C16 | 123.9 (10) | N2'—C16'—C15' | 121.0 (10) |
N2—C16—C17 | 121.1 (11) | C17'—C16'—C15' | 122.6 (11) |
N2—C16—C15 | 116.8 (8) | C18'—C17'—C16' | 121.7 (12) |
C17—C16—C15 | 121.7 (10) | C18'—C17'—H17' | 119.2 |
C18—C17—C16 | 120.3 (12) | C16'—C17'—H17' | 119.2 |
C18—C17—H17 | 119.8 | C17'—C18'—C19' | 119.5 (11) |
C16—C17—H17 | 119.8 | C17'—C18'—H18' | 120.3 |
C17—C18—C19 | 118.8 (10) | C19'—C18'—H18' | 120.3 |
C17—C18—H18 | 120.6 | C18'—C19'—C20' | 116.4 (12) |
C19—C18—H18 | 120.6 | C18'—C19'—H19' | 121.8 |
C20—C19—C18 | 116.5 (12) | C20'—C19'—H19' | 121.8 |
C20—C19—H19 | 121.8 | N2'—C20'—C19' | 122.5 (13) |
C18—C19—H19 | 121.8 | N2'—C20'—H20' | 118.8 |
N2—C20—C19 | 125.2 (12) | C19'—C20'—H20' | 118.8 |
N2—C20—H20 | 117.4 | C5'—C1'—C2' | 112.2 (11) |
C19—C20—H20 | 117.4 | C5'—C1'—Cl1' | 123.9 (10) |
C2—C1—C5 | 111.1 (11) | C2'—C1'—Cl1' | 123.8 (9) |
C2—C1—Cl1 | 127.6 (9) | C1'—C2'—C3' | 100.7 (9) |
C5—C1—Cl1 | 121.3 (10) | C1'—C2'—Pt' | 135.6 (8) |
C1—C2—C3 | 105.4 (10) | C3'—C2'—Pt' | 122.6 (8) |
C1—C2—Pt | 129.9 (8) | C4'—C3'—C2' | 109.7 (10) |
C3—C2—Pt | 123.7 (8) | C4'—C3'—H3' | 125.2 |
C4—C3—C2 | 109.1 (11) | C2'—C3'—H3' | 125.2 |
C4—C3—H3 | 125.4 | C5'—C4'—C3' | 109.3 (11) |
C2—C3—H3 | 125.4 | C5'—C4'—H4' | 125.4 |
C3—C4—C5 | 108.1 (11) | C3'—C4'—H4' | 125.4 |
C3—C4—H4 | 126.0 | C4'—C5'—C1' | 108.1 (11) |
C5—C4—H4 | 126.0 | C4'—C5'—H5' | 126.0 |
C1—C5—C4 | 106.3 (11) | C1'—C5'—H5' | 126.0 |
C1—C5—H5 | 126.8 | C7'—C6'—C10' | 108.0 |
C4—C5—H5 | 126.8 | C8'—C7'—C6' | 108.0 |
C7—C6—C10 | 108.0 | C8'—C7'—H7' | 126.0 |
C8—C7—C6 | 108.0 | C6'—C7'—H7' | 126.0 |
C8—C7—H7 | 126.0 | C7'—C8'—C9' | 108.0 |
C6—C7—H7 | 126.0 | C7'—C8'—H8' | 126.0 |
C9—C8—C7 | 108.0 | C9'—C8'—H8' | 126.0 |
C9—C8—H8 | 126.0 | C10'—C9'—C8' | 108.0 |
C7—C8—H8 | 126.0 | C10'—C9'—Cl4A | 125.7 (10) |
C10—C9—C8 | 108.0 | C8'—C9'—Cl4A | 126.0 (10) |
C10—C9—H9 | 126.0 | C10'—C9'—H9' | 126.0 |
C8—C9—H9 | 126.0 | C8'—C9'—H9' | 126.0 |
C9—C10—C6 | 108.0 | C9'—C10'—C6' | 108.0 |
C9—C10—Cl2B | 111.4 (10) | C9'—C10'—H6' | 131.0 |
C9—C10—H10 | 126.0 | C9'—C10'—H10' | 126.0 |
C6—C10—H10 | 126.0 | C6'—C10'—H10' | 126.0 |
C3M'—Pt'—C1M' | 90.1 (7) | H6'—C10'—H10' | 103.0 |
C3M'—Pt'—C2M' | 86.5 (6) |
Experimental details
Crystal data | |
Chemical formula | [Pt(CH3)3(C10H7Cl2Fe)(C10H8N2)] |
Mr | 650.28 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 295 |
a, b, c (Å) | 20.137 (4), 10.572 (5), 21.810 (6) |
β (°) | 103.71 (1) |
V (Å3) | 4511 (3) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 7.09 |
Crystal size (mm) | 0.28 × 0.28 × 0.05 |
Data collection | |
Diffractometer | Stoe Stadi-2 two-circle diffractometer |
Absorption correction | ψ scan local program |
Tmin, Tmax | 0.166, 0.670 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 7797, 7797, 5558 |
Rint | 0.009 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.061, 0.168, 1.08 |
No. of reflections | 7797 |
No. of parameters | 461 |
No. of restraints | 200 |
H-atom treatment | See text |
Δρmax, Δρmin (e Å−3) | 2.43, −1.13 |
Computer programs: local program, SHELX76 (Sheldrick, 1976), SHELXL97 (Sheldrick, 1997), PLATON (Spek, 2001), SHELXL97 and PLATON.
The title compound, (I), was prepared during an investigation into the stability and reactivity of PtIV compounds with four Pt—C σ-bonds. The structure of (I) (Fig. 1) shows that the three methyl groups are in the fac orientation and hence the ferrocenyl unit is trans to a methyl group. For one of the independent molecules, the Pt—Cmethyl distances are 2.072 (11), 2.082 (11) and 2.092 (11) Å, whilst the Pt—C(Cl2Fc) distance of 2.146 (11) Å lies trans to the longest Pt—Cmethyl distance. The principal distortions from regular octahedral geometry at Pt arise from the small bite angle [N1—Pt—N2 77.1 (3)°] of bipy and the angle C3M—Pt—N2 of 99.4 (5)°.
In one of the independent molecules, the C atoms of the cyclopentadienyl rings are in an eclipsed conformation, with a twist of only 0.5°, while in the other, they are staggered by 26.7°. The Fe centre lies 1.634 (5) Å out of the C1–C5 plane and 1.610 (9) Å from the C6–C10 plane, with a centroid–Fe–centroid angle of 177.8°; the corresponding values for Fe' in the second molecule are 1.657 (5) Å, 1.653 (9) Å and 173.1°.
In both molecules, the cyclopentadienyl rings are inclined at 4.8 (13)°. In one molecule, the disordered chlorines are twisted about the line connecting the ring centroids by 79.2 and 123.4°; in the other, the corresponding values are 82.9 and 116.2°. This is in contrast to the reported structures of other Cl2Fc complexes (Hollands et al., 1985; Blake et al., 2001) where the chlorines are eclipsed.