Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807020144/bt2342sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807020144/bt2342Isup2.hkl |
CCDC reference: 646684
Key indicators
- Single-crystal X-ray study
- T = 100 K
- Mean (C-C) = 0.005 Å
- Disorder in solvent or counterion
- R factor = 0.025
- wR factor = 0.062
- Data-to-parameter ratio = 21.9
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT220_ALERT_2_B Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.83 Ratio
Alert level C PLAT213_ALERT_2_C Atom C9 has ADP max/min Ratio ............. 3.10 prola PLAT213_ALERT_2_C Atom C13 has ADP max/min Ratio ............. 3.20 prola PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.81 Ratio PLAT302_ALERT_4_C Anion/Solvent Disorder ......................... 50.00 Perc. PLAT411_ALERT_2_C Short Inter H...H Contact H23 .. H39D .. 2.14 Ang. PLAT432_ALERT_2_C Short Inter X...Y Contact Cl3 .. C14 .. 3.20 Ang. PLAT432_ALERT_2_C Short Inter X...Y Contact C32 .. C32 .. 3.18 Ang. PLAT711_ALERT_1_C BOND Unknown or Inconsistent Label .......... CENT(C1 FE1 CENT(C1 PLAT711_ALERT_1_C BOND Unknown or Inconsistent Label .......... CENT(C3 FE1 CENT(C3 PLAT712_ALERT_1_C ANGLE Unknown or Inconsistent Label .......... CENT(C1 CENT(C1FE1 CENT(C3
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 10 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 6 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 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
For related literature, see: Bjelosevic et al. (2006); Clemente et al. (1986); Gan & Hor (1995); Mason et al. (1999); Puxty et al. (2005); Scarcia et al. (1988).
All H-atoms were placed in idealized locations and refined as riding with appropriate displacement coefficients Uiso(H) = 1.5 times Ueq(bearing atom) for methyl H atoms and Uiso(H) = 1.2 times Ueq(bearing atom) for all other H atoms.
c—H distances were set to
C(sp3)-H=1.00, C(sp3)-2H=0.99, C(sp3)-3H=0.98, C(sp2)-H=0.95 Å.
The C—Cl distances were restrained so that they were the same within 0.02Å for all components of the disordered dichloromethane molecule. The distance between the two Cl atoms in both components of the disordered molecule were restrained to be the same distance within 0.02A%.
There was one large peak (c.a. 1.64 e Å-3) observed near atom Pt1 in the final difference map and was considered noise.
The use of iron(II) ferrocenyl phosphine ligands in coordination chemistry has proven to be successful for various applications including catalysis where palladium, nickel and rhodium compounds are typically used and medical ones which use a platinum(II) metal center (Gan & Hor, 1995, Scarcia et al., 1988, Mason et al., 1999). One of the more commonly used ferrocenyl diphosphines is 1,1'-bis(diphenylphosphino)ferrocene (dppf).
The title compound was synthesized as one representative of a series of compounds for which a systematic kinetic analysis could be performed (Bjelosevic et al., 2006). The study targeted the kinetics of the ligand exchange rate at the platinum center and its dependence on the choice of substituents on the cyclopentadienyl ring which significantly affected the reaction kinetics (Puxty et al., 2005). The current crystal structure reveals that the acetate moiety is in a location close to the site of attack at the platinum atom for the entering ligand in support of the mechanistic model suggested earlier that included a hydrogen bonding interaction between the entering ligand and the acetate prior to ligand replacement (Puxty et al., 2005).
Compound (I) co-crystallizes in a 1:1 ratio with dichloromethane. The dichloromethane molecule is disordered over two positions in a 69.6 (2):30.4 (2) ratio. Compound (I) exhibits a distorted square planar geometry around atom Pt1 with the two phosphorous groups cis to each other. The P2—Pt1—P1 angle of 98.27 (3)° is significantly larger than 90° due to the geometry of the ferrocenyl moiety. Around the atom Pt1, atoms P1 and Cl1 are slightly below the least squares plane defined by atoms Pt1, P1, P2, Cl1, and Cl2 and atoms P2 and Cl2 are slightly above the plane. This distorted square planar geometry is typical for this class of compounds with cis substitution pattern (Table 1).
Atom Fe1 is almost equidistant from the centers of the two five-membered rings; Fe1-Centroid(C1—C5)=1.6392 (15)Å and Fe1-Centroid(C34—C38)=1.6496 (15) Å. The two five-membered rings are staggered with an angle of 24.7 (2)°. The cyclopentadienyl rings are not parallel to each other forming a dihedral angle of 4.32 (18)° between their least squares planes defined by the carbon atoms in the cyclopentadienyl rings. This angle is similar to the angle of 5.9° for a similar complex, PtCl2(1-[1',2-bis(diphenylphosphino)ferrocenyl]), (Clemente et al., 1986). The other geometrical parameters are typical.
For related literature, see: Bjelosevic et al. (2006); Clemente et al. (1986); Gan & Hor (1995); Mason et al. (1999); Puxty et al. (2005); Scarcia et al. (1988).
Data collection: SMART (Bruker, 2003); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Bruker, 2003); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL, publCIF (Westrip, 2007) and modiCIFer (reference?).
Fig. 1. Molecular Drawing of (I) shown with 30% probability ellipsoids. All hydrogen atoms and the solvent molecule are omitted for clarity. |
[FePtCl2(C17H14P)(C21H20O2P)]·CH2Cl2 | F(000) = 1952 |
Mr = 991.36 | Dx = 1.784 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 5453 reflections |
a = 10.512 (2) Å | θ = 2.2–26.4° |
b = 22.327 (5) Å | µ = 4.59 mm−1 |
c = 15.734 (3) Å | T = 100 K |
β = 91.95 (3)° | Plate, yellow |
V = 3690.6 (13) Å3 | 0.30 × 0.30 × 0.20 mm |
Z = 4 |
Bruker CCD-1000 area-detector diffractometer | 10208 independent reflections |
Radiation source: fine-focus sealed tube | 8965 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.036 |
0.30° ω scans | θmax = 29.5°, θmin = 1.6° |
Absorption correction: multi-scan (SADABS; Bruker, 2003) | h = −14→14 |
Tmin = 0.296, Tmax = 0.401 | k = −30→30 |
52878 measured reflections | l = −21→21 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.025 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.062 | H-atom parameters constrained |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0269P)2 + 6.0554P] where P = (Fo2 + 2Fc2)/3 |
10208 reflections | (Δ/σ)max = 0.004 |
466 parameters | Δρmax = 1.64 e Å−3 |
10 restraints | Δρmin = −0.92 e Å−3 |
[FePtCl2(C17H14P)(C21H20O2P)]·CH2Cl2 | V = 3690.6 (13) Å3 |
Mr = 991.36 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 10.512 (2) Å | µ = 4.59 mm−1 |
b = 22.327 (5) Å | T = 100 K |
c = 15.734 (3) Å | 0.30 × 0.30 × 0.20 mm |
β = 91.95 (3)° |
Bruker CCD-1000 area-detector diffractometer | 10208 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2003) | 8965 reflections with I > 2σ(I) |
Tmin = 0.296, Tmax = 0.401 | Rint = 0.036 |
52878 measured reflections |
R[F2 > 2σ(F2)] = 0.025 | 10 restraints |
wR(F2) = 0.062 | H-atom parameters constrained |
S = 1.04 | Δρmax = 1.64 e Å−3 |
10208 reflections | Δρmin = −0.92 e Å−3 |
466 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) | |
Pt1 | 0.140468 (8) | 0.132603 (4) | 0.758092 (6) | 0.01436 (3) | |
Fe1 | 0.54287 (3) | 0.114340 (19) | 0.80695 (3) | 0.01972 (8) | |
Cl1 | 0.00138 (7) | 0.10731 (3) | 0.64455 (5) | 0.02873 (15) | |
Cl2 | −0.03911 (6) | 0.12673 (3) | 0.84410 (5) | 0.02585 (15) | |
P1 | 0.30079 (6) | 0.14445 (3) | 0.66721 (4) | 0.01477 (12) | |
P2 | 0.25011 (6) | 0.15429 (3) | 0.88039 (4) | 0.01635 (12) | |
O1 | 0.2910 (2) | −0.01082 (9) | 0.68141 (17) | 0.0339 (5) | |
O2 | 0.1135 (2) | −0.02861 (12) | 0.7561 (2) | 0.0529 (8) | |
C1 | 0.5735 (3) | 0.12949 (13) | 0.68171 (19) | 0.0230 (6) | |
H1 | 0.5937 | 0.1690 | 0.6556 | 0.028* | |
C2 | 0.6635 (3) | 0.08684 (14) | 0.7132 (2) | 0.0282 (6) | |
H2 | 0.7581 | 0.0917 | 0.7146 | 0.034* | |
C3 | 0.5963 (3) | 0.03736 (14) | 0.7449 (2) | 0.0268 (6) | |
H3 | 0.6361 | 0.0014 | 0.7728 | 0.032* | |
C4 | 0.4624 (3) | 0.04795 (12) | 0.73472 (19) | 0.0217 (5) | |
C5 | 0.4477 (2) | 0.10615 (12) | 0.69515 (16) | 0.0173 (5) | |
C6 | 0.3573 (3) | 0.00707 (13) | 0.7602 (2) | 0.0265 (6) | |
H6 | 0.2973 | 0.0298 | 0.7962 | 0.032* | |
C7 | 0.4039 (3) | −0.04811 (15) | 0.8084 (3) | 0.0434 (9) | |
H7A | 0.3306 | −0.0712 | 0.8270 | 0.065* | |
H7B | 0.4561 | −0.0358 | 0.8582 | 0.065* | |
H7C | 0.4549 | −0.0729 | 0.7712 | 0.065* | |
C8 | 0.1648 (3) | −0.02605 (14) | 0.6894 (3) | 0.0441 (10) | |
C9 | 0.1061 (4) | −0.03844 (18) | 0.6032 (4) | 0.0662 (16) | |
H9A | 0.0998 | −0.0818 | 0.5945 | 0.099* | |
H9B | 0.1592 | −0.0209 | 0.5596 | 0.099* | |
H9C | 0.0209 | −0.0207 | 0.5991 | 0.099* | |
C10 | 0.2715 (3) | 0.12169 (13) | 0.55682 (18) | 0.0247 (6) | |
C11 | 0.3360 (4) | 0.07272 (14) | 0.5227 (2) | 0.0337 (7) | |
H11 | 0.3947 | 0.0504 | 0.5573 | 0.040* | |
C12 | 0.3135 (5) | 0.05697 (18) | 0.4381 (2) | 0.0532 (11) | |
H12 | 0.3568 | 0.0238 | 0.4148 | 0.064* | |
C13 | 0.2292 (6) | 0.0891 (2) | 0.3881 (2) | 0.0656 (15) | |
H13 | 0.2141 | 0.0779 | 0.3304 | 0.079* | |
C14 | 0.1652 (5) | 0.13809 (19) | 0.4209 (2) | 0.0515 (11) | |
H14 | 0.1067 | 0.1601 | 0.3857 | 0.062* | |
C15 | 0.1867 (3) | 0.15482 (15) | 0.50520 (19) | 0.0325 (7) | |
H15 | 0.1441 | 0.1885 | 0.5276 | 0.039* | |
C16 | 0.3434 (3) | 0.22291 (11) | 0.65452 (17) | 0.0186 (5) | |
C17 | 0.4092 (3) | 0.24223 (13) | 0.58355 (19) | 0.0287 (7) | |
H17 | 0.4325 | 0.2141 | 0.5415 | 0.034* | |
C18 | 0.4405 (4) | 0.30218 (14) | 0.5742 (2) | 0.0391 (9) | |
H18 | 0.4841 | 0.3149 | 0.5254 | 0.047* | |
C19 | 0.4084 (4) | 0.34376 (14) | 0.6359 (3) | 0.0406 (9) | |
H19 | 0.4315 | 0.3846 | 0.6299 | 0.049* | |
C20 | 0.3425 (3) | 0.32510 (13) | 0.7063 (2) | 0.0313 (7) | |
H20 | 0.3209 | 0.3532 | 0.7488 | 0.038* | |
C21 | 0.3084 (3) | 0.26527 (12) | 0.71437 (18) | 0.0222 (6) | |
H21 | 0.2604 | 0.2531 | 0.7614 | 0.027* | |
C22 | 0.2155 (3) | 0.23025 (13) | 0.91742 (16) | 0.0200 (5) | |
C23 | 0.1044 (3) | 0.25952 (13) | 0.88866 (17) | 0.0219 (5) | |
H23 | 0.0444 | 0.2389 | 0.8528 | 0.026* | |
C24 | 0.0811 (3) | 0.31836 (13) | 0.91199 (19) | 0.0273 (6) | |
H24 | 0.0059 | 0.3379 | 0.8915 | 0.033* | |
C25 | 0.1668 (4) | 0.34874 (16) | 0.9650 (2) | 0.0357 (7) | |
H25 | 0.1498 | 0.3888 | 0.9816 | 0.043* | |
C26 | 0.2771 (4) | 0.32076 (17) | 0.9936 (2) | 0.0378 (8) | |
H26 | 0.3365 | 0.3417 | 1.0294 | 0.045* | |
C27 | 0.3018 (3) | 0.26180 (15) | 0.97022 (18) | 0.0299 (7) | |
H27 | 0.3779 | 0.2429 | 0.9903 | 0.036* | |
C28 | 0.2114 (3) | 0.10271 (13) | 0.96601 (18) | 0.0234 (6) | |
C29 | 0.2326 (4) | 0.11993 (16) | 1.0500 (2) | 0.0373 (8) | |
H29 | 0.2623 | 0.1592 | 1.0627 | 0.045* | |
C30 | 0.2107 (4) | 0.07996 (19) | 1.1159 (2) | 0.0482 (10) | |
H30 | 0.2246 | 0.0923 | 1.1733 | 0.058* | |
C31 | 0.1692 (3) | 0.02311 (18) | 1.0985 (2) | 0.0427 (9) | |
H31 | 0.1538 | −0.0039 | 1.1436 | 0.051* | |
C32 | 0.1498 (3) | 0.00492 (16) | 1.0150 (2) | 0.0356 (8) | |
H32 | 0.1227 | −0.0349 | 1.0029 | 0.043* | |
C33 | 0.1696 (3) | 0.04486 (14) | 0.9482 (2) | 0.0284 (7) | |
H33 | 0.1547 | 0.0325 | 0.8910 | 0.034* | |
C34 | 0.4223 (3) | 0.15186 (13) | 0.88959 (17) | 0.0211 (5) | |
C35 | 0.4938 (3) | 0.10397 (15) | 0.93073 (18) | 0.0280 (6) | |
H35 | 0.4574 | 0.0670 | 0.9563 | 0.034* | |
C36 | 0.6248 (3) | 0.11869 (17) | 0.9281 (2) | 0.0343 (7) | |
H36 | 0.6968 | 0.0933 | 0.9504 | 0.041* | |
C37 | 0.6368 (3) | 0.17445 (16) | 0.8869 (2) | 0.0312 (7) | |
H37 | 0.7188 | 0.1951 | 0.8750 | 0.037* | |
C38 | 0.5133 (3) | 0.19534 (14) | 0.86199 (18) | 0.0235 (6) | |
H38 | 0.4931 | 0.2336 | 0.8315 | 0.028* | |
C39 | 0.8601 (3) | 0.24397 (18) | 0.6923 (2) | 0.0304 (9) | 0.696 (2) |
H39A | 0.8000 | 0.2360 | 0.6438 | 0.037* | 0.696 (2) |
H39B | 0.8837 | 0.2051 | 0.7187 | 0.037* | 0.696 (2) |
Cl3 | 0.78490 (15) | 0.28920 (6) | 0.76765 (8) | 0.0470 (4) | 0.696 (2) |
Cl4 | 0.99801 (16) | 0.27896 (7) | 0.65465 (13) | 0.0414 (4) | 0.696 (2) |
C39A | 0.8471 (3) | 0.2564 (4) | 0.7340 (6) | 0.0304 (9) | 0.304 (2) |
H39C | 0.8535 | 0.2133 | 0.7200 | 0.037* | 0.304 (2) |
H39D | 0.8622 | 0.2609 | 0.7961 | 0.037* | 0.304 (2) |
Cl3A | 0.69277 (19) | 0.28225 (10) | 0.70574 (14) | 0.0238 (6) | 0.304 (2) |
Cl4A | 0.9650 (3) | 0.29633 (19) | 0.6802 (2) | 0.0344 (8) | 0.304 (2) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Pt1 | 0.00934 (5) | 0.01389 (5) | 0.01969 (5) | −0.00178 (3) | −0.00177 (3) | 0.00457 (3) |
Fe1 | 0.01012 (16) | 0.02461 (19) | 0.02435 (19) | −0.00004 (14) | −0.00065 (14) | −0.00185 (15) |
Cl1 | 0.0204 (3) | 0.0288 (4) | 0.0360 (4) | −0.0063 (3) | −0.0132 (3) | 0.0016 (3) |
Cl2 | 0.0103 (3) | 0.0304 (4) | 0.0370 (4) | 0.0007 (2) | 0.0040 (3) | 0.0163 (3) |
P1 | 0.0165 (3) | 0.0132 (3) | 0.0146 (3) | −0.0020 (2) | 0.0008 (2) | −0.0004 (2) |
P2 | 0.0125 (3) | 0.0210 (3) | 0.0156 (3) | 0.0013 (2) | 0.0010 (2) | 0.0045 (2) |
O1 | 0.0251 (11) | 0.0188 (10) | 0.0568 (15) | −0.0033 (8) | −0.0124 (10) | 0.0002 (10) |
O2 | 0.0263 (13) | 0.0298 (14) | 0.102 (3) | −0.0060 (10) | −0.0009 (15) | 0.0286 (15) |
C1 | 0.0158 (12) | 0.0256 (14) | 0.0282 (14) | −0.0023 (10) | 0.0101 (11) | −0.0061 (11) |
C2 | 0.0153 (13) | 0.0317 (16) | 0.0380 (16) | 0.0015 (11) | 0.0067 (12) | −0.0071 (13) |
C3 | 0.0165 (13) | 0.0265 (15) | 0.0374 (16) | 0.0045 (11) | 0.0009 (12) | −0.0040 (12) |
C4 | 0.0164 (12) | 0.0186 (12) | 0.0300 (14) | 0.0002 (10) | −0.0009 (11) | −0.0016 (11) |
C5 | 0.0142 (11) | 0.0164 (12) | 0.0214 (12) | −0.0014 (9) | 0.0041 (9) | −0.0040 (10) |
C6 | 0.0191 (13) | 0.0201 (13) | 0.0402 (17) | −0.0005 (10) | −0.0031 (12) | 0.0084 (12) |
C7 | 0.0315 (18) | 0.0253 (16) | 0.073 (3) | −0.0003 (13) | −0.0084 (17) | 0.0212 (17) |
C8 | 0.0275 (17) | 0.0130 (14) | 0.090 (3) | 0.0004 (12) | −0.022 (2) | 0.0055 (17) |
C9 | 0.046 (2) | 0.0266 (18) | 0.123 (4) | −0.0008 (17) | −0.046 (3) | −0.018 (2) |
C10 | 0.0342 (16) | 0.0212 (13) | 0.0184 (12) | −0.0010 (11) | −0.0039 (11) | −0.0030 (10) |
C11 | 0.052 (2) | 0.0248 (15) | 0.0242 (14) | 0.0048 (14) | −0.0014 (14) | −0.0081 (12) |
C12 | 0.092 (3) | 0.038 (2) | 0.0300 (18) | 0.013 (2) | −0.005 (2) | −0.0174 (16) |
C13 | 0.116 (4) | 0.058 (3) | 0.0215 (17) | 0.016 (3) | −0.015 (2) | −0.0196 (17) |
C14 | 0.078 (3) | 0.054 (2) | 0.0217 (16) | 0.010 (2) | −0.0167 (18) | −0.0029 (16) |
C15 | 0.0456 (19) | 0.0310 (16) | 0.0203 (14) | 0.0033 (14) | −0.0060 (13) | −0.0029 (12) |
C16 | 0.0219 (13) | 0.0130 (11) | 0.0214 (12) | −0.0019 (10) | 0.0060 (10) | 0.0019 (10) |
C17 | 0.0404 (17) | 0.0190 (13) | 0.0278 (15) | −0.0012 (12) | 0.0187 (13) | −0.0010 (11) |
C18 | 0.053 (2) | 0.0224 (15) | 0.0441 (19) | −0.0042 (14) | 0.0318 (17) | 0.0038 (14) |
C19 | 0.051 (2) | 0.0149 (14) | 0.058 (2) | −0.0083 (14) | 0.0297 (18) | −0.0017 (14) |
C20 | 0.0409 (18) | 0.0178 (13) | 0.0364 (16) | −0.0050 (12) | 0.0196 (14) | −0.0068 (12) |
C21 | 0.0260 (14) | 0.0192 (13) | 0.0218 (13) | −0.0037 (11) | 0.0089 (11) | 0.0003 (10) |
C22 | 0.0216 (13) | 0.0267 (14) | 0.0121 (11) | −0.0002 (11) | 0.0049 (10) | 0.0021 (10) |
C23 | 0.0245 (14) | 0.0234 (14) | 0.0183 (12) | 0.0013 (11) | 0.0070 (10) | 0.0031 (10) |
C24 | 0.0326 (16) | 0.0236 (14) | 0.0264 (14) | 0.0042 (12) | 0.0113 (12) | 0.0002 (11) |
C25 | 0.044 (2) | 0.0330 (17) | 0.0312 (16) | −0.0003 (15) | 0.0155 (15) | −0.0109 (14) |
C26 | 0.0405 (19) | 0.046 (2) | 0.0272 (15) | −0.0040 (16) | 0.0042 (14) | −0.0209 (15) |
C27 | 0.0302 (16) | 0.0414 (18) | 0.0178 (13) | 0.0018 (13) | −0.0004 (12) | −0.0087 (12) |
C28 | 0.0187 (12) | 0.0290 (15) | 0.0229 (13) | 0.0067 (11) | 0.0050 (10) | 0.0145 (11) |
C29 | 0.052 (2) | 0.0364 (18) | 0.0235 (15) | 0.0128 (16) | 0.0060 (14) | 0.0121 (13) |
C30 | 0.069 (3) | 0.050 (2) | 0.0272 (16) | 0.020 (2) | 0.0116 (17) | 0.0220 (16) |
C31 | 0.0352 (18) | 0.054 (2) | 0.0397 (19) | 0.0125 (16) | 0.0086 (15) | 0.0339 (17) |
C32 | 0.0168 (13) | 0.0384 (18) | 0.052 (2) | 0.0036 (12) | 0.0017 (13) | 0.0280 (16) |
C33 | 0.0142 (12) | 0.0350 (16) | 0.0361 (16) | 0.0033 (11) | 0.0023 (11) | 0.0170 (13) |
C34 | 0.0159 (12) | 0.0294 (14) | 0.0177 (12) | 0.0019 (11) | −0.0031 (10) | −0.0006 (11) |
C35 | 0.0209 (14) | 0.0400 (18) | 0.0227 (13) | 0.0071 (13) | −0.0058 (11) | 0.0038 (12) |
C36 | 0.0186 (14) | 0.051 (2) | 0.0321 (16) | 0.0086 (13) | −0.0103 (12) | −0.0041 (15) |
C37 | 0.0135 (13) | 0.0427 (18) | 0.0372 (17) | −0.0039 (12) | −0.0039 (12) | −0.0112 (14) |
C38 | 0.0150 (12) | 0.0300 (15) | 0.0254 (13) | −0.0023 (11) | −0.0011 (10) | −0.0065 (11) |
C39 | 0.041 (2) | 0.024 (2) | 0.026 (2) | 0.0047 (17) | −0.008 (2) | −0.0019 (18) |
Cl3 | 0.0678 (10) | 0.0327 (7) | 0.0404 (7) | 0.0192 (6) | 0.0008 (6) | −0.0052 (5) |
Cl4 | 0.0288 (8) | 0.0394 (8) | 0.0549 (10) | 0.0054 (6) | −0.0143 (7) | −0.0115 (7) |
C39A | 0.041 (2) | 0.024 (2) | 0.026 (2) | 0.0047 (17) | −0.008 (2) | −0.0019 (18) |
Cl3A | 0.0242 (11) | 0.0223 (11) | 0.0249 (11) | 0.0004 (8) | 0.0022 (8) | 0.0040 (8) |
Cl4A | 0.0214 (14) | 0.045 (2) | 0.0365 (17) | −0.0101 (13) | −0.0052 (12) | 0.0154 (15) |
Pt1—P2 | 2.2615 (9) | C14—H14 | 0.9500 |
Pt1—P1 | 2.2625 (9) | C15—H15 | 0.9500 |
Pt1—Cl1 | 2.3388 (10) | C16—C21 | 1.393 (4) |
Pt1—Cl2 | 2.3635 (9) | C16—C17 | 1.401 (4) |
Fe1—C5 | 2.002 (3) | C17—C18 | 1.388 (4) |
Fe1—C34 | 2.028 (3) | C17—H17 | 0.9500 |
Fe1—C4 | 2.034 (3) | C18—C19 | 1.393 (5) |
Fe1—C38 | 2.034 (3) | C18—H18 | 0.9500 |
Fe1—C1 | 2.036 (3) | C19—C20 | 1.391 (4) |
Fe1—C35 | 2.045 (3) | C19—H19 | 0.9500 |
Fe1—C37 | 2.067 (3) | C20—C21 | 1.390 (4) |
Fe1—C36 | 2.067 (3) | C20—H20 | 0.9500 |
Fe1—C3 | 2.064 (3) | C21—H21 | 0.9500 |
Fe1—C2 | 2.070 (3) | C22—C23 | 1.400 (4) |
Fe1—Cent(C1-C5) | 1.6392 (15) | C22—C27 | 1.399 (4) |
Fe1—Cent(C34-C38) | 1.6496 (15) | C23—C24 | 1.388 (4) |
P1—C5 | 1.806 (3) | C23—H23 | 0.9500 |
P1—C16 | 1.821 (3) | C24—C25 | 1.384 (5) |
P1—C10 | 1.826 (3) | C24—H24 | 0.9500 |
P2—C34 | 1.812 (3) | C25—C26 | 1.379 (5) |
P2—C28 | 1.829 (3) | C25—H25 | 0.9500 |
P2—C22 | 1.834 (3) | C26—C27 | 1.394 (5) |
O1—C8 | 1.379 (4) | C26—H26 | 0.9500 |
O1—C6 | 1.457 (4) | C27—H27 | 0.9500 |
O2—C8 | 1.198 (5) | C28—C33 | 1.390 (5) |
C1—C2 | 1.419 (4) | C28—C29 | 1.387 (4) |
C1—C5 | 1.444 (4) | C29—C30 | 1.393 (4) |
C1—H1 | 1.0000 | C29—H29 | 0.9500 |
C2—C3 | 1.411 (4) | C30—C31 | 1.367 (6) |
C2—H2 | 1.0000 | C30—H30 | 0.9500 |
C3—C4 | 1.431 (4) | C31—C32 | 1.384 (6) |
C3—H3 | 1.0000 | C31—H31 | 0.9500 |
C4—C5 | 1.447 (4) | C32—C33 | 1.399 (4) |
C4—C6 | 1.498 (4) | C32—H32 | 0.9500 |
C6—C7 | 1.519 (4) | C33—H33 | 0.9500 |
C6—H6 | 1.0000 | C34—C38 | 1.440 (4) |
C7—H7A | 0.9800 | C34—C35 | 1.447 (4) |
C7—H7B | 0.9800 | C35—C36 | 1.417 (4) |
C7—H7C | 0.9800 | C35—H35 | 1.0000 |
C8—C9 | 1.496 (6) | C36—C37 | 1.412 (5) |
C9—H9A | 0.9800 | C36—H36 | 1.0000 |
C9—H9B | 0.9800 | C37—C38 | 1.422 (4) |
C9—H9C | 0.9800 | C37—H37 | 1.0000 |
C10—C15 | 1.397 (4) | C38—H38 | 1.0000 |
C10—C11 | 1.402 (4) | C39—Cl3 | 1.765 (3) |
C11—C12 | 1.390 (4) | C39—Cl4 | 1.766 (3) |
C11—H11 | 0.9500 | C39—H39A | 0.9900 |
C12—C13 | 1.368 (6) | C39—H39B | 0.9900 |
C12—H12 | 0.9500 | C39A—Cl3A | 1.765 (3) |
C13—C14 | 1.393 (6) | C39A—Cl4A | 1.765 (3) |
C13—H13 | 0.9500 | C39A—H39C | 0.9900 |
C14—C15 | 1.389 (4) | C39A—H39D | 0.9900 |
P2—Pt1—P1 | 98.27 (3) | H9B—C9—H9C | 109.5 |
P2—Pt1—Cl1 | 171.43 (3) | C15—C10—C11 | 119.8 (3) |
P1—Pt1—Cl1 | 90.29 (3) | C15—C10—P1 | 119.3 (2) |
P2—Pt1—Cl2 | 85.33 (3) | C11—C10—P1 | 120.8 (2) |
P1—Pt1—Cl2 | 174.27 (2) | C12—C11—C10 | 119.7 (3) |
Cl1—Pt1—Cl2 | 86.18 (3) | C12—C11—H11 | 120.2 |
Cent(C1-C5)—Fe1—Cent(C34-C38) | 178.55 (8) | C10—C11—H11 | 120.2 |
C5—Fe1—C34 | 107.25 (11) | C13—C12—C11 | 120.3 (4) |
C5—Fe1—C4 | 42.00 (11) | C13—C12—H12 | 119.9 |
C34—Fe1—C4 | 113.71 (11) | C11—C12—H12 | 119.9 |
C5—Fe1—C38 | 112.10 (11) | C12—C13—C14 | 120.7 (3) |
C34—Fe1—C38 | 41.54 (11) | C12—C13—H13 | 119.7 |
C4—Fe1—C38 | 144.99 (11) | C14—C13—H13 | 119.7 |
C5—Fe1—C1 | 41.88 (10) | C13—C14—C15 | 120.0 (4) |
C34—Fe1—C1 | 132.46 (11) | C13—C14—H14 | 120.0 |
C4—Fe1—C1 | 69.93 (12) | C15—C14—H14 | 120.0 |
C38—Fe1—C1 | 107.22 (12) | C14—C15—C10 | 119.5 (3) |
C5—Fe1—C35 | 133.78 (11) | C14—C15—H15 | 120.2 |
C34—Fe1—C35 | 41.64 (12) | C10—C15—H15 | 120.2 |
C4—Fe1—C35 | 109.64 (13) | C21—C16—C17 | 118.6 (2) |
C38—Fe1—C35 | 69.38 (13) | C21—C16—P1 | 120.5 (2) |
C1—Fe1—C35 | 173.79 (12) | C17—C16—P1 | 120.9 (2) |
C5—Fe1—C37 | 143.88 (13) | C18—C17—C16 | 120.5 (3) |
C34—Fe1—C37 | 68.77 (12) | C18—C17—H17 | 119.8 |
C4—Fe1—C37 | 173.62 (13) | C16—C17—H17 | 119.8 |
C38—Fe1—C37 | 40.58 (12) | C17—C18—C19 | 120.3 (3) |
C1—Fe1—C37 | 113.13 (13) | C17—C18—H18 | 119.8 |
C35—Fe1—C37 | 67.97 (14) | C19—C18—H18 | 119.8 |
C5—Fe1—C36 | 173.98 (12) | C20—C19—C18 | 119.7 (3) |
C34—Fe1—C36 | 68.84 (12) | C20—C19—H19 | 120.2 |
C4—Fe1—C36 | 134.56 (14) | C18—C19—H19 | 120.2 |
C38—Fe1—C36 | 68.31 (13) | C19—C20—C21 | 119.8 (3) |
C1—Fe1—C36 | 144.12 (13) | C19—C20—H20 | 120.1 |
C35—Fe1—C36 | 40.31 (13) | C21—C20—H20 | 120.1 |
C37—Fe1—C36 | 39.93 (14) | C20—C21—C16 | 121.1 (3) |
C5—Fe1—C3 | 69.16 (12) | C20—C21—H21 | 119.5 |
C34—Fe1—C3 | 146.47 (12) | C16—C21—H21 | 119.5 |
C4—Fe1—C3 | 40.87 (11) | C23—C22—C27 | 118.3 (3) |
C38—Fe1—C3 | 171.88 (12) | C23—C22—P2 | 120.1 (2) |
C1—Fe1—C3 | 68.02 (12) | C27—C22—P2 | 121.5 (2) |
C35—Fe1—C3 | 115.97 (13) | C24—C23—C22 | 120.6 (3) |
C37—Fe1—C3 | 134.12 (12) | C24—C23—H23 | 119.7 |
C36—Fe1—C3 | 111.34 (13) | C22—C23—H23 | 119.7 |
C5—Fe1—C2 | 69.32 (11) | C25—C24—C23 | 120.4 (3) |
C34—Fe1—C2 | 172.15 (13) | C25—C24—H24 | 119.8 |
C4—Fe1—C2 | 68.85 (12) | C23—C24—H24 | 119.8 |
C38—Fe1—C2 | 132.32 (12) | C26—C25—C24 | 119.8 (3) |
C1—Fe1—C2 | 40.44 (12) | C26—C25—H25 | 120.1 |
C35—Fe1—C2 | 145.61 (13) | C24—C25—H25 | 120.1 |
C37—Fe1—C2 | 109.53 (12) | C25—C26—C27 | 120.2 (3) |
C36—Fe1—C2 | 115.15 (13) | C25—C26—H26 | 119.9 |
C3—Fe1—C2 | 39.90 (12) | C27—C26—H26 | 119.9 |
C5—P1—C16 | 105.70 (12) | C26—C27—C22 | 120.7 (3) |
C5—P1—C10 | 102.41 (13) | C26—C27—H27 | 119.7 |
C16—P1—C10 | 101.40 (13) | C22—C27—H27 | 119.7 |
C5—P1—Pt1 | 116.09 (9) | C33—C28—C29 | 119.3 (3) |
C16—P1—Pt1 | 111.91 (9) | C33—C28—P2 | 120.9 (2) |
C10—P1—Pt1 | 117.62 (11) | C29—C28—P2 | 119.7 (3) |
C34—P2—C28 | 99.73 (13) | C30—C29—C28 | 120.4 (4) |
C34—P2—C22 | 102.17 (13) | C30—C29—H29 | 119.8 |
C28—P2—C22 | 107.27 (13) | C28—C29—H29 | 119.8 |
C34—P2—Pt1 | 122.71 (9) | C31—C30—C29 | 120.3 (4) |
C28—P2—Pt1 | 111.86 (11) | C31—C30—H30 | 119.8 |
C22—P2—Pt1 | 111.57 (9) | C29—C30—H30 | 119.8 |
C8—O1—C6 | 115.1 (3) | C30—C31—C32 | 120.0 (3) |
C2—C1—C5 | 108.0 (3) | C30—C31—H31 | 120.0 |
C2—C1—Fe1 | 71.10 (18) | C32—C31—H31 | 120.0 |
C5—C1—Fe1 | 67.81 (15) | C31—C32—C33 | 120.3 (4) |
C2—C1—H1 | 126.0 | C31—C32—H32 | 119.8 |
C5—C1—H1 | 126.0 | C33—C32—H32 | 119.8 |
Fe1—C1—H1 | 126.0 | C28—C33—C32 | 119.7 (3) |
C3—C2—C1 | 108.3 (3) | C28—C33—H33 | 120.1 |
C3—C2—Fe1 | 69.82 (17) | C32—C33—H33 | 120.1 |
C1—C2—Fe1 | 68.46 (16) | C38—C34—C35 | 107.0 (2) |
C3—C2—H2 | 125.9 | C38—C34—P2 | 128.9 (2) |
C1—C2—H2 | 125.9 | C35—C34—P2 | 124.1 (2) |
Fe1—C2—H2 | 125.9 | C38—C34—Fe1 | 69.46 (16) |
C2—C3—C4 | 109.5 (3) | C35—C34—Fe1 | 69.81 (17) |
C2—C3—Fe1 | 70.28 (17) | P2—C34—Fe1 | 127.29 (15) |
C4—C3—Fe1 | 68.44 (16) | C36—C35—C34 | 107.8 (3) |
C2—C3—H3 | 125.2 | C36—C35—Fe1 | 70.70 (19) |
C4—C3—H3 | 125.2 | C34—C35—Fe1 | 68.55 (16) |
Fe1—C3—H3 | 125.2 | C36—C35—H35 | 126.1 |
C3—C4—C5 | 106.7 (2) | C34—C35—H35 | 126.1 |
C3—C4—C6 | 126.9 (3) | Fe1—C35—H35 | 126.1 |
C5—C4—C6 | 126.4 (2) | C37—C36—C35 | 108.7 (3) |
C3—C4—Fe1 | 70.69 (17) | C37—C36—Fe1 | 70.02 (18) |
C5—C4—Fe1 | 67.81 (15) | C35—C36—Fe1 | 68.99 (17) |
C6—C4—Fe1 | 126.2 (2) | C37—C36—H36 | 125.6 |
C1—C5—C4 | 107.6 (2) | C35—C36—H36 | 125.6 |
C1—C5—P1 | 125.0 (2) | Fe1—C36—H36 | 125.6 |
C4—C5—P1 | 127.42 (19) | C36—C37—C38 | 108.7 (3) |
C1—C5—Fe1 | 70.30 (16) | C36—C37—Fe1 | 70.04 (19) |
C4—C5—Fe1 | 70.19 (16) | C38—C37—Fe1 | 68.45 (17) |
P1—C5—Fe1 | 124.61 (14) | C36—C37—H37 | 125.6 |
O1—C6—C4 | 105.9 (2) | C38—C37—H37 | 125.6 |
O1—C6—C7 | 109.8 (3) | Fe1—C37—H37 | 125.6 |
C4—C6—C7 | 113.6 (3) | C37—C38—C34 | 107.8 (3) |
O1—C6—H6 | 109.1 | C37—C38—Fe1 | 70.97 (18) |
C4—C6—H6 | 109.1 | C34—C38—Fe1 | 69.00 (17) |
C7—C6—H6 | 109.1 | C37—C38—H38 | 126.1 |
C6—C7—H7A | 109.5 | C34—C38—H38 | 126.1 |
C6—C7—H7B | 109.5 | Fe1—C38—H38 | 126.1 |
H7A—C7—H7B | 109.5 | Cl3—C39—Cl4 | 111.3 (2) |
C6—C7—H7C | 109.5 | Cl3—C39—H39A | 109.4 |
H7A—C7—H7C | 109.5 | Cl4—C39—H39A | 109.4 |
H7B—C7—H7C | 109.5 | Cl3—C39—H39B | 109.4 |
O2—C8—O1 | 123.7 (4) | Cl4—C39—H39B | 109.4 |
O2—C8—C9 | 126.9 (4) | H39A—C39—H39B | 108.0 |
O1—C8—C9 | 109.4 (4) | Cl3A—C39A—Cl4A | 111.6 (3) |
C8—C9—H9A | 109.5 | Cl3A—C39A—H39C | 109.3 |
C8—C9—H9B | 109.5 | Cl4A—C39A—H39C | 109.3 |
H9A—C9—H9B | 109.5 | Cl3A—C39A—H39D | 109.3 |
C8—C9—H9C | 109.5 | Cl4A—C39A—H39D | 109.3 |
H9A—C9—H9C | 109.5 | H39C—C39A—H39D | 108.0 |
P2—Pt1—P1—C5 | 49.63 (10) | C13—C14—C15—C10 | −0.9 (7) |
Cl1—Pt1—P1—C5 | −129.92 (10) | C11—C10—C15—C14 | 1.3 (5) |
P2—Pt1—P1—C16 | −71.81 (10) | P1—C10—C15—C14 | 179.3 (3) |
Cl1—Pt1—P1—C16 | 108.63 (10) | C5—P1—C16—C21 | −108.5 (2) |
P2—Pt1—P1—C10 | 171.38 (11) | C10—P1—C16—C21 | 145.0 (2) |
Cl1—Pt1—P1—C10 | −8.17 (11) | Pt1—P1—C16—C21 | 18.8 (3) |
P1—Pt1—P2—C34 | −19.00 (12) | C5—P1—C16—C17 | 73.1 (3) |
Cl2—Pt1—P2—C34 | 165.49 (12) | C10—P1—C16—C17 | −33.4 (3) |
P1—Pt1—P2—C28 | −137.29 (10) | Pt1—P1—C16—C17 | −159.6 (2) |
Cl2—Pt1—P2—C28 | 47.20 (10) | C21—C16—C17—C18 | 1.2 (5) |
P1—Pt1—P2—C22 | 102.55 (9) | P1—C16—C17—C18 | 179.6 (3) |
Cl2—Pt1—P2—C22 | −72.96 (9) | C16—C17—C18—C19 | 0.9 (6) |
C5—Fe1—C1—C2 | −119.5 (2) | C17—C18—C19—C20 | −1.2 (6) |
C4—Fe1—C1—C2 | −80.58 (18) | C18—C19—C20—C21 | −0.4 (6) |
C38—Fe1—C1—C2 | 136.32 (17) | C19—C20—C21—C16 | 2.5 (5) |
C37—Fe1—C1—C2 | 93.40 (19) | C17—C16—C21—C20 | −2.8 (5) |
C36—Fe1—C1—C2 | 59.7 (3) | P1—C16—C21—C20 | 178.7 (3) |
C3—Fe1—C1—C2 | −36.69 (17) | C34—P2—C22—C23 | 153.1 (2) |
C34—Fe1—C1—C5 | −65.3 (2) | C28—P2—C22—C23 | −102.5 (2) |
C4—Fe1—C1—C5 | 38.95 (15) | Pt1—P2—C22—C23 | 20.3 (2) |
C38—Fe1—C1—C5 | −104.15 (16) | C34—P2—C22—C27 | −22.8 (3) |
C37—Fe1—C1—C5 | −147.07 (16) | C28—P2—C22—C27 | 81.6 (3) |
C36—Fe1—C1—C5 | 179.2 (2) | Pt1—P2—C22—C27 | −155.6 (2) |
C3—Fe1—C1—C5 | 82.84 (17) | C27—C22—C23—C24 | 0.1 (4) |
C2—Fe1—C1—C5 | 119.5 (2) | P2—C22—C23—C24 | −175.9 (2) |
C5—C1—C2—C3 | 0.7 (3) | C22—C23—C24—C25 | −0.8 (4) |
Fe1—C1—C2—C3 | 58.6 (2) | C23—C24—C25—C26 | 1.1 (5) |
C5—C1—C2—Fe1 | −57.91 (19) | C24—C25—C26—C27 | −0.8 (5) |
C5—Fe1—C2—C3 | −81.87 (19) | C25—C26—C27—C22 | 0.1 (5) |
C4—Fe1—C2—C3 | −36.76 (18) | C23—C22—C27—C26 | 0.2 (4) |
C38—Fe1—C2—C3 | 176.58 (18) | P2—C22—C27—C26 | 176.2 (2) |
C1—Fe1—C2—C3 | −120.3 (3) | C34—P2—C28—C33 | −104.3 (2) |
C35—Fe1—C2—C3 | 57.4 (3) | C22—P2—C28—C33 | 149.6 (2) |
C37—Fe1—C2—C3 | 136.66 (19) | Pt1—P2—C28—C33 | 26.9 (3) |
C36—Fe1—C2—C3 | 93.7 (2) | C34—P2—C28—C29 | 71.0 (3) |
C5—Fe1—C2—C1 | 38.38 (17) | C22—P2—C28—C29 | −35.1 (3) |
C4—Fe1—C2—C1 | 83.50 (18) | Pt1—P2—C28—C29 | −157.8 (2) |
C38—Fe1—C2—C1 | −63.2 (2) | C33—C28—C29—C30 | −0.8 (5) |
C35—Fe1—C2—C1 | 177.7 (2) | P2—C28—C29—C30 | −176.2 (3) |
C37—Fe1—C2—C1 | −103.08 (19) | C28—C29—C30—C31 | 0.7 (6) |
C36—Fe1—C2—C1 | −146.00 (19) | C29—C30—C31—C32 | 0.5 (6) |
C3—Fe1—C2—C1 | 120.3 (3) | C30—C31—C32—C33 | −1.4 (5) |
C1—C2—C3—C4 | −0.5 (4) | C29—C28—C33—C32 | −0.1 (4) |
Fe1—C2—C3—C4 | 57.3 (2) | P2—C28—C33—C32 | 175.3 (2) |
C1—C2—C3—Fe1 | −57.8 (2) | C31—C32—C33—C28 | 1.2 (4) |
C5—Fe1—C3—C2 | 82.31 (19) | C28—P2—C34—C38 | −157.2 (3) |
C34—Fe1—C3—C2 | 172.3 (2) | C22—P2—C34—C38 | −47.0 (3) |
C4—Fe1—C3—C2 | 121.5 (3) | Pt1—P2—C34—C38 | 78.8 (3) |
C1—Fe1—C3—C2 | 37.17 (18) | C28—P2—C34—C35 | 20.6 (3) |
C35—Fe1—C3—C2 | −148.04 (18) | C22—P2—C34—C35 | 130.8 (3) |
C37—Fe1—C3—C2 | −64.3 (3) | Pt1—P2—C34—C35 | −103.4 (2) |
C36—Fe1—C3—C2 | −104.1 (2) | C28—P2—C34—Fe1 | 110.1 (2) |
C5—Fe1—C3—C4 | −39.17 (17) | C22—P2—C34—Fe1 | −139.72 (18) |
C34—Fe1—C3—C4 | 50.8 (3) | Pt1—P2—C34—Fe1 | −13.9 (2) |
C1—Fe1—C3—C4 | −84.31 (19) | C5—Fe1—C34—C38 | −104.10 (17) |
C35—Fe1—C3—C4 | 90.5 (2) | C4—Fe1—C34—C38 | −148.58 (17) |
C37—Fe1—C3—C4 | 174.23 (19) | C1—Fe1—C34—C38 | −64.7 (2) |
C36—Fe1—C3—C4 | 134.40 (19) | C35—Fe1—C34—C38 | 118.1 (2) |
C2—Fe1—C3—C4 | −121.5 (3) | C37—Fe1—C34—C38 | 37.79 (18) |
C2—C3—C4—C5 | 0.1 (3) | C36—Fe1—C34—C38 | 80.76 (19) |
Fe1—C3—C4—C5 | 58.50 (19) | C3—Fe1—C34—C38 | 177.8 (2) |
C2—C3—C4—C6 | −179.7 (3) | C5—Fe1—C34—C35 | 137.83 (18) |
Fe1—C3—C4—C6 | −121.3 (3) | C4—Fe1—C34—C35 | 93.35 (19) |
C2—C3—C4—Fe1 | −58.4 (2) | C38—Fe1—C34—C35 | −118.1 (2) |
C5—Fe1—C4—C3 | 118.1 (2) | C1—Fe1—C34—C35 | 177.25 (18) |
C34—Fe1—C4—C3 | −152.12 (18) | C37—Fe1—C34—C35 | −80.3 (2) |
C38—Fe1—C4—C3 | 170.8 (2) | C36—Fe1—C34—C35 | −37.32 (19) |
C1—Fe1—C4—C3 | 79.24 (19) | C3—Fe1—C34—C35 | 59.7 (3) |
C35—Fe1—C4—C3 | −107.35 (19) | C5—Fe1—C34—P2 | 19.8 (2) |
C36—Fe1—C4—C3 | −69.1 (2) | C4—Fe1—C34—P2 | −24.7 (2) |
C2—Fe1—C4—C3 | 35.92 (18) | C38—Fe1—C34—P2 | 123.9 (3) |
C34—Fe1—C4—C5 | 89.79 (17) | C1—Fe1—C34—P2 | 59.2 (3) |
C38—Fe1—C4—C5 | 52.7 (3) | C35—Fe1—C34—P2 | −118.1 (3) |
C1—Fe1—C4—C5 | −38.85 (15) | C37—Fe1—C34—P2 | 161.6 (2) |
C35—Fe1—C4—C5 | 134.56 (15) | C36—Fe1—C34—P2 | −155.4 (2) |
C36—Fe1—C4—C5 | 172.85 (17) | C3—Fe1—C34—P2 | −58.4 (3) |
C3—Fe1—C4—C5 | −118.1 (2) | C38—C34—C35—C36 | 0.3 (3) |
C2—Fe1—C4—C5 | −82.17 (17) | P2—C34—C35—C36 | −177.9 (2) |
C5—Fe1—C4—C6 | −119.7 (3) | Fe1—C34—C35—C36 | 60.0 (2) |
C34—Fe1—C4—C6 | −30.0 (3) | C38—C34—C35—Fe1 | −59.77 (19) |
C38—Fe1—C4—C6 | −67.0 (3) | P2—C34—C35—Fe1 | 122.0 (2) |
C1—Fe1—C4—C6 | −158.6 (3) | C5—Fe1—C35—C36 | 178.29 (19) |
C35—Fe1—C4—C6 | 14.8 (3) | C34—Fe1—C35—C36 | −119.1 (3) |
C36—Fe1—C4—C6 | 53.1 (3) | C4—Fe1—C35—C36 | 137.0 (2) |
C3—Fe1—C4—C6 | 122.2 (3) | C38—Fe1—C35—C36 | −80.4 (2) |
C2—Fe1—C4—C6 | 158.1 (3) | C37—Fe1—C35—C36 | −36.7 (2) |
C2—C1—C5—C4 | −0.6 (3) | C3—Fe1—C35—C36 | 93.0 (2) |
Fe1—C1—C5—C4 | −60.58 (18) | C2—Fe1—C35—C36 | 56.0 (3) |
C2—C1—C5—P1 | 179.0 (2) | C5—Fe1—C35—C34 | −62.6 (2) |
Fe1—C1—C5—P1 | 119.1 (2) | C4—Fe1—C35—C34 | −103.96 (18) |
C2—C1—C5—Fe1 | 60.0 (2) | C38—Fe1—C35—C34 | 38.69 (17) |
C3—C4—C5—C1 | 0.3 (3) | C37—Fe1—C35—C34 | 82.37 (19) |
C6—C4—C5—C1 | −179.9 (3) | C36—Fe1—C35—C34 | 119.1 (3) |
Fe1—C4—C5—C1 | 60.65 (18) | C3—Fe1—C35—C34 | −147.97 (17) |
C3—C4—C5—P1 | −179.3 (2) | C2—Fe1—C35—C34 | 175.1 (2) |
C6—C4—C5—P1 | 0.5 (4) | C34—C35—C36—C37 | 0.2 (4) |
Fe1—C4—C5—P1 | −119.0 (2) | Fe1—C35—C36—C37 | 58.9 (2) |
C3—C4—C5—Fe1 | −60.3 (2) | C34—C35—C36—Fe1 | −58.7 (2) |
C6—C4—C5—Fe1 | 119.5 (3) | C34—Fe1—C36—C37 | −81.8 (2) |
C16—P1—C5—C1 | −18.4 (3) | C4—Fe1—C36—C37 | 175.25 (18) |
C10—P1—C5—C1 | 87.4 (2) | C38—Fe1—C36—C37 | −37.03 (18) |
Pt1—P1—C5—C1 | −143.1 (2) | C1—Fe1—C36—C37 | 52.6 (3) |
C16—P1—C5—C4 | 161.2 (2) | C35—Fe1—C36—C37 | −120.3 (3) |
C10—P1—C5—C4 | −93.0 (3) | C3—Fe1—C36—C37 | 134.25 (19) |
Pt1—P1—C5—C4 | 36.5 (3) | C2—Fe1—C36—C37 | 90.8 (2) |
C16—P1—C5—Fe1 | 70.64 (18) | C34—Fe1—C36—C35 | 38.51 (19) |
C10—P1—C5—Fe1 | 176.43 (16) | C4—Fe1—C36—C35 | −64.4 (3) |
Pt1—P1—C5—Fe1 | −54.06 (18) | C38—Fe1—C36—C35 | 83.3 (2) |
C34—Fe1—C5—C1 | 135.43 (16) | C1—Fe1—C36—C35 | 172.9 (2) |
C4—Fe1—C5—C1 | −118.1 (2) | C37—Fe1—C36—C35 | 120.3 (3) |
C38—Fe1—C5—C1 | 91.47 (17) | C3—Fe1—C36—C35 | −105.4 (2) |
C35—Fe1—C5—C1 | 173.59 (18) | C2—Fe1—C36—C35 | −148.9 (2) |
C37—Fe1—C5—C1 | 58.0 (2) | C35—C36—C37—C38 | −0.6 (4) |
C3—Fe1—C5—C1 | −79.91 (17) | Fe1—C36—C37—C38 | 57.6 (2) |
C2—Fe1—C5—C1 | −37.10 (17) | C35—C36—C37—Fe1 | −58.3 (2) |
C34—Fe1—C5—C4 | −106.52 (17) | C5—Fe1—C37—C36 | 172.42 (19) |
C38—Fe1—C5—C4 | −150.48 (16) | C34—Fe1—C37—C36 | 82.0 (2) |
C1—Fe1—C5—C4 | 118.1 (2) | C38—Fe1—C37—C36 | 120.6 (3) |
C35—Fe1—C5—C4 | −68.4 (2) | C1—Fe1—C37—C36 | −149.58 (18) |
C37—Fe1—C5—C4 | 176.05 (19) | C35—Fe1—C37—C36 | 37.05 (18) |
C3—Fe1—C5—C4 | 38.15 (16) | C3—Fe1—C37—C36 | −68.4 (3) |
C2—Fe1—C5—C4 | 80.96 (17) | C2—Fe1—C37—C36 | −106.2 (2) |
C34—Fe1—C5—P1 | 15.9 (2) | C5—Fe1—C37—C38 | 51.8 (3) |
C4—Fe1—C5—P1 | 122.4 (2) | C34—Fe1—C37—C38 | −38.65 (18) |
C38—Fe1—C5—P1 | −28.0 (2) | C1—Fe1—C37—C38 | 89.8 (2) |
C1—Fe1—C5—P1 | −119.5 (2) | C35—Fe1—C37—C38 | −83.60 (19) |
C35—Fe1—C5—P1 | 54.1 (2) | C36—Fe1—C37—C38 | −120.6 (3) |
C37—Fe1—C5—P1 | −61.5 (3) | C3—Fe1—C37—C38 | 171.00 (18) |
C3—Fe1—C5—P1 | 160.6 (2) | C2—Fe1—C37—C38 | 133.17 (19) |
C2—Fe1—C5—P1 | −156.6 (2) | C36—C37—C38—C34 | 0.8 (4) |
C8—O1—C6—C4 | −153.3 (2) | Fe1—C37—C38—C34 | 59.4 (2) |
C8—O1—C6—C7 | 83.6 (3) | C36—C37—C38—Fe1 | −58.6 (2) |
C3—C4—C6—O1 | −115.0 (3) | C35—C34—C38—C37 | −0.7 (3) |
C5—C4—C6—O1 | 65.2 (4) | P2—C34—C38—C37 | 177.4 (2) |
Fe1—C4—C6—O1 | 152.9 (2) | Fe1—C34—C38—C37 | −60.7 (2) |
C3—C4—C6—C7 | 5.7 (5) | C35—C34—C38—Fe1 | 60.0 (2) |
C5—C4—C6—C7 | −174.1 (3) | P2—C34—C38—Fe1 | −121.9 (2) |
Fe1—C4—C6—C7 | −86.5 (3) | C5—Fe1—C38—C37 | −150.01 (19) |
C6—O1—C8—O2 | −4.8 (4) | C34—Fe1—C38—C37 | 118.6 (3) |
C6—O1—C8—C9 | 175.3 (3) | C1—Fe1—C38—C37 | −105.7 (2) |
C5—P1—C10—C15 | −162.0 (3) | C35—Fe1—C38—C37 | 79.8 (2) |
C16—P1—C10—C15 | −52.9 (3) | C36—Fe1—C38—C37 | 36.5 (2) |
Pt1—P1—C10—C15 | 69.4 (3) | C2—Fe1—C38—C37 | −68.4 (2) |
C5—P1—C10—C11 | 15.9 (3) | C5—Fe1—C38—C34 | 91.40 (17) |
C16—P1—C10—C11 | 125.0 (3) | C4—Fe1—C38—C34 | 56.3 (3) |
Pt1—P1—C10—C11 | −112.6 (3) | C1—Fe1—C38—C34 | 135.72 (16) |
C15—C10—C11—C12 | −1.0 (5) | C35—Fe1—C38—C34 | −38.78 (16) |
P1—C10—C11—C12 | −178.9 (3) | C37—Fe1—C38—C34 | −118.6 (3) |
C10—C11—C12—C13 | 0.2 (7) | C36—Fe1—C38—C34 | −82.13 (18) |
C11—C12—C13—C14 | 0.3 (8) | C2—Fe1—C38—C34 | 173.01 (17) |
C12—C13—C14—C15 | 0.1 (8) |
Experimental details
Crystal data | |
Chemical formula | [FePtCl2(C17H14P)(C21H20O2P)]·CH2Cl2 |
Mr | 991.36 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 100 |
a, b, c (Å) | 10.512 (2), 22.327 (5), 15.734 (3) |
β (°) | 91.95 (3) |
V (Å3) | 3690.6 (13) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 4.59 |
Crystal size (mm) | 0.30 × 0.30 × 0.20 |
Data collection | |
Diffractometer | Bruker CCD-1000 area-detector |
Absorption correction | Multi-scan (SADABS; Bruker, 2003) |
Tmin, Tmax | 0.296, 0.401 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 52878, 10208, 8965 |
Rint | 0.036 |
(sin θ/λ)max (Å−1) | 0.693 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.025, 0.062, 1.04 |
No. of reflections | 10208 |
No. of parameters | 466 |
No. of restraints | 10 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 1.64, −0.92 |
Computer programs: SMART (Bruker, 2003), SAINT (Bruker, 2003), SAINT, SHELXTL (Bruker, 2003), SHELXTL, publCIF (Westrip, 2007) and modiCIFer (reference?).
angle | angle, ° | average angle, ° for relevant references in the CSD | number of relevant references in the CSD |
P1—Pt1—Cl1 | 90.29 (3) | 88 (3) | 7 |
P2—Pt1—Cl2 | 85.33 (3) | 88 (2) | 7 |
Cl1—Pt1—Cl2 | 86.18 (3) | 87 (1) | 7 |
P2—Pt1—P1 | 98.27 (3) | 99 (4) | 7 |
CSD (Cambridge Structural Database; Version 5.28, January 2007 release; Allen, 2002) |
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The use of iron(II) ferrocenyl phosphine ligands in coordination chemistry has proven to be successful for various applications including catalysis where palladium, nickel and rhodium compounds are typically used and medical ones which use a platinum(II) metal center (Gan & Hor, 1995, Scarcia et al., 1988, Mason et al., 1999). One of the more commonly used ferrocenyl diphosphines is 1,1'-bis(diphenylphosphino)ferrocene (dppf).
The title compound was synthesized as one representative of a series of compounds for which a systematic kinetic analysis could be performed (Bjelosevic et al., 2006). The study targeted the kinetics of the ligand exchange rate at the platinum center and its dependence on the choice of substituents on the cyclopentadienyl ring which significantly affected the reaction kinetics (Puxty et al., 2005). The current crystal structure reveals that the acetate moiety is in a location close to the site of attack at the platinum atom for the entering ligand in support of the mechanistic model suggested earlier that included a hydrogen bonding interaction between the entering ligand and the acetate prior to ligand replacement (Puxty et al., 2005).
Compound (I) co-crystallizes in a 1:1 ratio with dichloromethane. The dichloromethane molecule is disordered over two positions in a 69.6 (2):30.4 (2) ratio. Compound (I) exhibits a distorted square planar geometry around atom Pt1 with the two phosphorous groups cis to each other. The P2—Pt1—P1 angle of 98.27 (3)° is significantly larger than 90° due to the geometry of the ferrocenyl moiety. Around the atom Pt1, atoms P1 and Cl1 are slightly below the least squares plane defined by atoms Pt1, P1, P2, Cl1, and Cl2 and atoms P2 and Cl2 are slightly above the plane. This distorted square planar geometry is typical for this class of compounds with cis substitution pattern (Table 1).
Atom Fe1 is almost equidistant from the centers of the two five-membered rings; Fe1-Centroid(C1—C5)=1.6392 (15)Å and Fe1-Centroid(C34—C38)=1.6496 (15) Å. The two five-membered rings are staggered with an angle of 24.7 (2)°. The cyclopentadienyl rings are not parallel to each other forming a dihedral angle of 4.32 (18)° between their least squares planes defined by the carbon atoms in the cyclopentadienyl rings. This angle is similar to the angle of 5.9° for a similar complex, PtCl2(1-[1',2-bis(diphenylphosphino)ferrocenyl]), (Clemente et al., 1986). The other geometrical parameters are typical.