






Supporting information
![]() | Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536808038294/nc2123sup1.cif |
![]() | Structure factor file (CIF format) https://doi.org/10.1107/S1600536808038294/nc2123Isup2.hkl |
CCDC reference: 712328
Key indicators
- Single-crystal X-ray study
- T = 162 K
- Mean
(C-C) = 0.004 Å
- R factor = 0.038
- wR factor = 0.083
- Data-to-parameter ratio = 22.3
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT420_ALERT_2_B D-H Without Acceptor O1 - H1A ... ?
Alert level C Value of measurement temperature given = 162.000 Value of melting point given = 0.000 PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.62 Ratio
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 30.50 From the CIF: _reflns_number_total 9131 Count of symmetry unique reflns 5301 Completeness (_total/calc) 172.25% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 3830 Fraction of Friedel pairs measured 0.723 Are heavy atom types Z>Si present yes PLAT791_ALERT_4_G The Model has Chirality at C11 (Verify) .... S
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 1 ALERT level C = Check and explain 2 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 0 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
The preparation of the title compound has been reported by Lotz & Spindler (2005). Crystals were obtained from a solution of the title compound in a mixture of chloroform and n-hexane.
H atoms were geometrically positioned using distances: Cplanar—H=0.95 Å, Cprimary—H=1.00 Å, Uiso(H)=1.2Ueq(C). The H atom of the hydroxy group was taken from a difference Fourier synthesis and was refined with an isotropic thermal parameter. Friedel opposites were not averaged. The absolute configuration was determined from 4069 Friedel pairs.
Data collection: SMART (Siemens, 1995); cell refinement: SMART (Siemens, 1995); data reduction: SAINT (Siemens, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).
![]() | Fig. 1. The structure of the title compound shown with 50% probability displacement ellipsoids. The H atoms are drawn as small spheres of arbitrary radius. |
[Fe(C5H5)(C36H29OP2)] | F(000) = 688 |
Mr = 660.47 | Dx = 1.343 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2yb | Cell parameters from 239 reflections |
a = 11.6111 (15) Å | θ = 3–23° |
b = 8.6154 (10) Å | µ = 0.59 mm−1 |
c = 16.481 (2) Å | T = 162 K |
β = 97.807 (12)° | Block, orange |
V = 1633.4 (3) Å3 | 0.40 × 0.40 × 0.32 mm |
Z = 2 |
Siemens SMART 1K CCD diffractometer | 9131 independent reflections |
Radiation source: normal-focus sealed tube | 7926 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.051 |
ω scans | θmax = 30.5°, θmin = 1.8° |
Absorption correction: numerical (SHELXTL; Sheldrick, 2008) | h = −16→16 |
Tmin = 0.795, Tmax = 0.845 | k = −12→12 |
25293 measured reflections | l = −23→23 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.038 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.083 | w = 1/[σ2(Fo2) + (0.03P)2 + 0.5P] where P = (Fo2 + 2Fc2)/3 |
S = 1.07 | (Δ/σ)max = 0.003 |
9131 reflections | Δρmax = 0.33 e Å−3 |
410 parameters | Δρmin = −0.23 e Å−3 |
1 restraint | Absolute structure: Flack (1983), 4069 Friedel pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: −0.023 (10) |
[Fe(C5H5)(C36H29OP2)] | V = 1633.4 (3) Å3 |
Mr = 660.47 | Z = 2 |
Monoclinic, P21 | Mo Kα radiation |
a = 11.6111 (15) Å | µ = 0.59 mm−1 |
b = 8.6154 (10) Å | T = 162 K |
c = 16.481 (2) Å | 0.40 × 0.40 × 0.32 mm |
β = 97.807 (12)° |
Siemens SMART 1K CCD diffractometer | 9131 independent reflections |
Absorption correction: numerical (SHELXTL; Sheldrick, 2008) | 7926 reflections with I > 2σ(I) |
Tmin = 0.795, Tmax = 0.845 | Rint = 0.051 |
25293 measured reflections |
R[F2 > 2σ(F2)] = 0.038 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.083 | Δρmax = 0.33 e Å−3 |
S = 1.07 | Δρmin = −0.23 e Å−3 |
9131 reflections | Absolute structure: Flack (1983), 4069 Friedel pairs |
410 parameters | Absolute structure parameter: −0.023 (10) |
1 restraint |
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 | ||
Fe1 | 0.19359 (2) | −0.01898 (3) | 0.741420 (18) | 0.02801 (7) | |
P1 | 0.62868 (4) | 0.27356 (6) | 0.85276 (3) | 0.02329 (11) | |
P2 | 0.32422 (4) | 0.33294 (6) | 0.71106 (3) | 0.02413 (11) | |
O1 | 0.47730 (15) | −0.14478 (19) | 0.81532 (11) | 0.0352 (4) | |
C1 | 0.35814 (16) | −0.0009 (2) | 0.71422 (12) | 0.0249 (4) | |
C2 | 0.30376 (19) | −0.1365 (3) | 0.67651 (15) | 0.0319 (5) | |
H2A | 0.3304 | −0.2402 | 0.6853 | 0.038* | |
C3 | 0.2027 (2) | −0.0890 (3) | 0.62352 (16) | 0.0360 (5) | |
H3A | 0.1499 | −0.1559 | 0.5913 | 0.043* | |
C4 | 0.19426 (19) | 0.0751 (3) | 0.62691 (14) | 0.0310 (5) | |
H4A | 0.1349 | 0.1367 | 0.5973 | 0.037* | |
C5 | 0.29067 (17) | 0.1323 (2) | 0.68279 (12) | 0.0244 (4) | |
C6 | 0.2085 (2) | −0.0518 (3) | 0.86549 (16) | 0.0466 (7) | |
H6A | 0.2790 | −0.0574 | 0.9021 | 0.056* | |
C7 | 0.1497 (3) | −0.1778 (4) | 0.8229 (2) | 0.0585 (9) | |
H7A | 0.1742 | −0.2831 | 0.8260 | 0.070* | |
C8 | 0.0498 (3) | −0.1210 (4) | 0.7757 (2) | 0.0567 (8) | |
H8A | −0.0053 | −0.1812 | 0.7413 | 0.068* | |
C9 | 0.0444 (2) | 0.0418 (4) | 0.78764 (17) | 0.0445 (6) | |
H9A | −0.0144 | 0.1098 | 0.7628 | 0.053* | |
C10 | 0.1430 (2) | 0.0839 (3) | 0.84353 (14) | 0.0365 (5) | |
H10A | 0.1619 | 0.1858 | 0.8630 | 0.044* | |
C11 | 0.46677 (16) | 0.0034 (2) | 0.77503 (12) | 0.0255 (4) | |
H11A | 0.4583 | 0.0857 | 0.8166 | 0.031* | |
C12 | 0.57475 (16) | 0.0380 (2) | 0.73482 (12) | 0.0232 (4) | |
C13 | 0.59482 (18) | −0.0521 (2) | 0.66787 (13) | 0.0306 (5) | |
H13A | 0.5415 | −0.1319 | 0.6489 | 0.037* | |
C14 | 0.69159 (18) | −0.0268 (3) | 0.62852 (13) | 0.0345 (5) | |
H14A | 0.7051 | −0.0905 | 0.5837 | 0.041* | |
C15 | 0.76792 (19) | 0.0911 (3) | 0.65477 (14) | 0.0341 (5) | |
H15A | 0.8330 | 0.1109 | 0.6271 | 0.041* | |
C16 | 0.74938 (18) | 0.1810 (3) | 0.72182 (13) | 0.0272 (4) | |
H16A | 0.8024 | 0.2621 | 0.7394 | 0.033* | |
C17 | 0.65449 (17) | 0.1546 (2) | 0.76401 (12) | 0.0224 (4) | |
C18 | 0.64664 (17) | 0.1267 (2) | 0.93453 (12) | 0.0247 (4) | |
C19 | 0.59727 (19) | 0.1590 (3) | 1.00546 (13) | 0.0309 (5) | |
H19A | 0.5589 | 0.2553 | 1.0102 | 0.037* | |
C20 | 0.6035 (2) | 0.0530 (3) | 1.06872 (14) | 0.0380 (5) | |
H20A | 0.5703 | 0.0774 | 1.1168 | 0.046* | |
C21 | 0.6582 (2) | −0.0893 (3) | 1.06242 (14) | 0.0345 (5) | |
H21A | 0.6609 | −0.1630 | 1.1055 | 0.041* | |
C22 | 0.70842 (19) | −0.1230 (3) | 0.99310 (13) | 0.0312 (5) | |
H22A | 0.7463 | −0.2198 | 0.9888 | 0.037* | |
C23 | 0.70385 (16) | −0.0159 (3) | 0.92957 (12) | 0.0284 (4) | |
H23A | 0.7397 | −0.0395 | 0.8825 | 0.034* | |
C24 | 0.76505 (18) | 0.3831 (3) | 0.87543 (13) | 0.0284 (4) | |
C25 | 0.8662 (2) | 0.3235 (3) | 0.91878 (17) | 0.0450 (6) | |
H25A | 0.8679 | 0.2187 | 0.9369 | 0.054* | |
C26 | 0.9648 (2) | 0.4150 (4) | 0.93611 (19) | 0.0574 (8) | |
H26A | 1.0332 | 0.3731 | 0.9663 | 0.069* | |
C27 | 0.9636 (3) | 0.5670 (4) | 0.90944 (17) | 0.0511 (8) | |
H27A | 1.0310 | 0.6298 | 0.9215 | 0.061* | |
C28 | 0.8645 (3) | 0.6274 (3) | 0.86535 (19) | 0.0492 (7) | |
H28A | 0.8642 | 0.7313 | 0.8460 | 0.059* | |
C29 | 0.7647 (2) | 0.5367 (3) | 0.84906 (16) | 0.0369 (5) | |
H29A | 0.6960 | 0.5798 | 0.8198 | 0.044* | |
C30 | 0.19045 (17) | 0.4249 (2) | 0.65968 (13) | 0.0268 (4) | |
C31 | 0.0981 (2) | 0.4392 (3) | 0.70517 (14) | 0.0334 (5) | |
H31A | 0.1085 | 0.4098 | 0.7612 | 0.040* | |
C32 | −0.00866 (19) | 0.4957 (3) | 0.66960 (15) | 0.0399 (5) | |
H32A | −0.0713 | 0.5027 | 0.7010 | 0.048* | |
C33 | −0.0244 (2) | 0.5420 (3) | 0.58854 (17) | 0.0431 (6) | |
H33A | −0.0975 | 0.5809 | 0.5642 | 0.052* | |
C34 | 0.0673 (2) | 0.5313 (4) | 0.54313 (16) | 0.0473 (7) | |
H34A | 0.0572 | 0.5635 | 0.4875 | 0.057* | |
C35 | 0.17429 (18) | 0.4734 (3) | 0.57875 (13) | 0.0367 (5) | |
H35A | 0.2369 | 0.4670 | 0.5473 | 0.044* | |
C36 | 0.43404 (17) | 0.3780 (2) | 0.64374 (12) | 0.0249 (4) | |
C37 | 0.45399 (18) | 0.2857 (3) | 0.57774 (13) | 0.0301 (4) | |
H37A | 0.4039 | 0.2006 | 0.5620 | 0.036* | |
C38 | 0.54639 (19) | 0.3165 (3) | 0.53441 (14) | 0.0348 (5) | |
H38A | 0.5595 | 0.2522 | 0.4898 | 0.042* | |
C39 | 0.6192 (2) | 0.4415 (3) | 0.55664 (15) | 0.0377 (6) | |
H39A | 0.6822 | 0.4630 | 0.5271 | 0.045* | |
C40 | 0.6003 (2) | 0.5345 (3) | 0.62161 (17) | 0.0378 (5) | |
H40A | 0.6501 | 0.6203 | 0.6365 | 0.045* | |
C41 | 0.50852 (17) | 0.5034 (2) | 0.66566 (14) | 0.0301 (4) | |
H41A | 0.4965 | 0.5675 | 0.7107 | 0.036* | |
H1A | 0.532 (2) | −0.146 (3) | 0.8487 (17) | 0.034 (7)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Fe1 | 0.02189 (13) | 0.02740 (15) | 0.03497 (16) | −0.00588 (13) | 0.00474 (11) | 0.00120 (13) |
P1 | 0.0218 (2) | 0.0242 (2) | 0.0240 (2) | −0.00007 (19) | 0.00343 (19) | −0.0001 (2) |
P2 | 0.0264 (2) | 0.0262 (3) | 0.0196 (2) | −0.0037 (2) | 0.00265 (18) | −0.0002 (2) |
O1 | 0.0310 (8) | 0.0341 (9) | 0.0392 (9) | −0.0060 (7) | 0.0002 (7) | 0.0144 (7) |
C1 | 0.0224 (8) | 0.0251 (10) | 0.0276 (9) | −0.0054 (8) | 0.0049 (7) | −0.0012 (8) |
C2 | 0.0293 (11) | 0.0288 (11) | 0.0380 (12) | −0.0044 (9) | 0.0062 (9) | −0.0060 (9) |
C3 | 0.0340 (12) | 0.0360 (12) | 0.0370 (13) | −0.0084 (10) | 0.0006 (10) | −0.0089 (10) |
C4 | 0.0283 (11) | 0.0328 (12) | 0.0300 (11) | −0.0047 (9) | −0.0024 (9) | −0.0023 (9) |
C5 | 0.0230 (9) | 0.0262 (10) | 0.0241 (10) | −0.0055 (8) | 0.0032 (7) | 0.0005 (8) |
C6 | 0.0403 (12) | 0.063 (2) | 0.0393 (13) | 0.0053 (12) | 0.0143 (10) | 0.0198 (12) |
C7 | 0.0666 (19) | 0.0405 (15) | 0.078 (2) | −0.0039 (14) | 0.0434 (17) | 0.0172 (15) |
C8 | 0.0426 (15) | 0.0584 (19) | 0.074 (2) | −0.0285 (14) | 0.0247 (14) | −0.0143 (16) |
C9 | 0.0246 (11) | 0.0599 (17) | 0.0501 (15) | 0.0002 (11) | 0.0098 (10) | 0.0011 (13) |
C10 | 0.0364 (12) | 0.0422 (14) | 0.0328 (12) | −0.0073 (10) | 0.0113 (10) | 0.0005 (10) |
C11 | 0.0260 (9) | 0.0249 (11) | 0.0262 (9) | −0.0024 (8) | 0.0053 (7) | 0.0023 (8) |
C12 | 0.0219 (9) | 0.0245 (9) | 0.0230 (9) | 0.0006 (7) | 0.0022 (7) | 0.0039 (7) |
C13 | 0.0302 (10) | 0.0309 (12) | 0.0304 (11) | −0.0023 (8) | 0.0031 (8) | −0.0042 (8) |
C14 | 0.0369 (10) | 0.0417 (12) | 0.0267 (10) | 0.0016 (11) | 0.0103 (8) | −0.0050 (11) |
C15 | 0.0276 (10) | 0.0458 (13) | 0.0311 (11) | 0.0004 (9) | 0.0120 (9) | 0.0007 (10) |
C16 | 0.0238 (10) | 0.0305 (11) | 0.0280 (10) | −0.0031 (8) | 0.0058 (8) | 0.0013 (9) |
C17 | 0.0206 (9) | 0.0258 (10) | 0.0206 (9) | 0.0028 (7) | 0.0018 (7) | 0.0031 (7) |
C18 | 0.0213 (9) | 0.0288 (10) | 0.0233 (9) | −0.0035 (8) | 0.0008 (7) | 0.0009 (8) |
C19 | 0.0348 (11) | 0.0328 (11) | 0.0265 (10) | 0.0005 (9) | 0.0092 (9) | −0.0043 (9) |
C20 | 0.0468 (13) | 0.0450 (13) | 0.0246 (11) | 0.0002 (11) | 0.0140 (10) | −0.0016 (10) |
C21 | 0.0383 (12) | 0.0403 (13) | 0.0248 (11) | −0.0008 (10) | 0.0045 (9) | 0.0090 (9) |
C22 | 0.0314 (10) | 0.0345 (11) | 0.0269 (11) | 0.0053 (9) | 0.0008 (8) | 0.0033 (8) |
C23 | 0.0285 (9) | 0.0334 (10) | 0.0241 (9) | 0.0056 (10) | 0.0066 (7) | 0.0033 (9) |
C24 | 0.0297 (10) | 0.0302 (11) | 0.0257 (10) | −0.0069 (8) | 0.0056 (8) | −0.0048 (8) |
C25 | 0.0334 (12) | 0.0499 (15) | 0.0488 (15) | −0.0136 (12) | −0.0047 (10) | 0.0138 (12) |
C26 | 0.0378 (14) | 0.083 (2) | 0.0483 (16) | −0.0260 (15) | −0.0056 (12) | 0.0108 (15) |
C27 | 0.0493 (16) | 0.0645 (19) | 0.0433 (15) | −0.0342 (14) | 0.0194 (13) | −0.0207 (14) |
C28 | 0.0579 (17) | 0.0324 (13) | 0.0644 (18) | −0.0186 (12) | 0.0343 (15) | −0.0121 (12) |
C29 | 0.0401 (12) | 0.0304 (11) | 0.0434 (13) | −0.0024 (9) | 0.0167 (10) | −0.0038 (10) |
C30 | 0.0267 (9) | 0.0261 (10) | 0.0278 (10) | −0.0013 (8) | 0.0041 (8) | −0.0010 (8) |
C31 | 0.0383 (12) | 0.0312 (12) | 0.0330 (11) | 0.0020 (9) | 0.0130 (9) | 0.0015 (9) |
C32 | 0.0330 (11) | 0.0404 (13) | 0.0489 (14) | 0.0020 (11) | 0.0149 (10) | 0.0006 (12) |
C33 | 0.0271 (11) | 0.0507 (15) | 0.0502 (15) | 0.0051 (10) | 0.0009 (10) | 0.0023 (12) |
C34 | 0.0368 (13) | 0.071 (2) | 0.0337 (13) | 0.0077 (12) | 0.0017 (10) | 0.0095 (12) |
C35 | 0.0302 (10) | 0.0532 (14) | 0.0276 (10) | 0.0050 (11) | 0.0068 (8) | 0.0037 (11) |
C36 | 0.0249 (9) | 0.0246 (10) | 0.0247 (10) | 0.0011 (8) | 0.0016 (7) | 0.0041 (8) |
C37 | 0.0311 (10) | 0.0330 (11) | 0.0256 (10) | −0.0017 (9) | 0.0018 (8) | 0.0027 (9) |
C38 | 0.0355 (11) | 0.0439 (13) | 0.0258 (10) | 0.0052 (10) | 0.0070 (9) | 0.0047 (9) |
C39 | 0.0322 (11) | 0.0399 (14) | 0.0432 (13) | 0.0044 (9) | 0.0136 (10) | 0.0164 (10) |
C40 | 0.0315 (11) | 0.0270 (11) | 0.0553 (15) | −0.0037 (9) | 0.0073 (10) | 0.0118 (10) |
C41 | 0.0283 (9) | 0.0239 (11) | 0.0379 (11) | 0.0009 (8) | 0.0042 (8) | 0.0041 (9) |
Fe1—C1 | 2.0269 (18) | C16—C17 | 1.399 (3) |
Fe1—C7 | 2.030 (3) | C16—H16A | 0.9500 |
Fe1—C8 | 2.033 (3) | C18—C19 | 1.398 (3) |
Fe1—C2 | 2.044 (2) | C18—C23 | 1.405 (3) |
Fe1—C6 | 2.048 (3) | C19—C20 | 1.380 (3) |
Fe1—C5 | 2.049 (2) | C19—H19A | 0.9500 |
Fe1—C3 | 2.051 (3) | C20—C21 | 1.391 (3) |
Fe1—C9 | 2.053 (2) | C20—H20A | 0.9500 |
Fe1—C4 | 2.055 (2) | C21—C22 | 1.382 (3) |
Fe1—C10 | 2.057 (2) | C21—H21A | 0.9500 |
P1—C24 | 1.837 (2) | C22—C23 | 1.391 (3) |
P1—C18 | 1.839 (2) | C22—H22A | 0.9500 |
P1—C17 | 1.843 (2) | C23—H23A | 0.9500 |
P2—C5 | 1.818 (2) | C24—C25 | 1.387 (3) |
P2—C36 | 1.842 (2) | C24—C29 | 1.393 (3) |
P2—C30 | 1.844 (2) | C25—C26 | 1.388 (4) |
O1—C11 | 1.437 (3) | C25—H25A | 0.9500 |
O1—H1A | 0.78 (3) | C26—C27 | 1.381 (4) |
C1—C2 | 1.429 (3) | C26—H26A | 0.9500 |
C1—C5 | 1.446 (3) | C27—C28 | 1.376 (4) |
C1—C11 | 1.501 (3) | C27—H27A | 0.9500 |
C2—C3 | 1.424 (3) | C28—C29 | 1.394 (3) |
C2—H2A | 0.9500 | C28—H28A | 0.9500 |
C3—C4 | 1.419 (3) | C29—H29A | 0.9500 |
C3—H3A | 0.9500 | C30—C35 | 1.386 (3) |
C4—C5 | 1.437 (3) | C30—C31 | 1.395 (3) |
C4—H4A | 0.9500 | C31—C32 | 1.386 (3) |
C6—C10 | 1.415 (4) | C31—H31A | 0.9500 |
C6—C7 | 1.416 (5) | C32—C33 | 1.382 (4) |
C6—H6A | 0.9500 | C32—H32A | 0.9500 |
C7—C8 | 1.395 (5) | C33—C34 | 1.385 (3) |
C7—H7A | 0.9500 | C33—H33A | 0.9500 |
C8—C9 | 1.418 (4) | C34—C35 | 1.392 (3) |
C8—H8A | 0.9500 | C34—H34A | 0.9500 |
C9—C10 | 1.416 (4) | C35—H35A | 0.9500 |
C9—H9A | 0.9500 | C36—C37 | 1.392 (3) |
C10—H10A | 0.9500 | C36—C41 | 1.400 (3) |
C11—C12 | 1.525 (3) | C37—C38 | 1.393 (3) |
C11—H11A | 1.0000 | C37—H37A | 0.9500 |
C12—C13 | 1.394 (3) | C38—C39 | 1.387 (3) |
C12—C17 | 1.406 (3) | C38—H38A | 0.9500 |
C13—C14 | 1.389 (3) | C39—C40 | 1.378 (4) |
C13—H13A | 0.9500 | C39—H39A | 0.9500 |
C14—C15 | 1.379 (3) | C40—C41 | 1.395 (3) |
C14—H14A | 0.9500 | C40—H40A | 0.9500 |
C15—C16 | 1.390 (3) | C41—H41A | 0.9500 |
C15—H15A | 0.9500 | ||
C1—Fe1—C7 | 121.78 (11) | C8—C9—H9A | 126.4 |
C1—Fe1—C8 | 158.24 (11) | Fe1—C9—H9A | 126.2 |
C7—Fe1—C8 | 40.16 (14) | C6—C10—C9 | 108.3 (2) |
C1—Fe1—C2 | 41.10 (8) | C6—C10—Fe1 | 69.50 (15) |
C7—Fe1—C2 | 104.11 (11) | C9—C10—Fe1 | 69.69 (14) |
C8—Fe1—C2 | 121.82 (11) | C6—C10—H10A | 125.9 |
C1—Fe1—C6 | 106.09 (9) | C9—C10—H10A | 125.9 |
C7—Fe1—C6 | 40.62 (13) | Fe1—C10—H10A | 126.5 |
C8—Fe1—C6 | 67.92 (13) | O1—C11—C1 | 107.29 (16) |
C2—Fe1—C6 | 118.70 (10) | O1—C11—C12 | 110.55 (16) |
C1—Fe1—C5 | 41.54 (8) | C1—C11—C12 | 112.37 (16) |
C7—Fe1—C5 | 160.76 (12) | O1—C11—H11A | 108.9 |
C8—Fe1—C5 | 158.57 (12) | C1—C11—H11A | 108.9 |
C2—Fe1—C5 | 69.20 (9) | C12—C11—H11A | 108.9 |
C6—Fe1—C5 | 125.55 (10) | C13—C12—C17 | 119.70 (18) |
C1—Fe1—C3 | 68.98 (9) | C13—C12—C11 | 118.09 (18) |
C7—Fe1—C3 | 118.61 (12) | C17—C12—C11 | 122.20 (17) |
C8—Fe1—C3 | 106.64 (12) | C14—C13—C12 | 121.0 (2) |
C2—Fe1—C3 | 40.70 (10) | C14—C13—H13A | 119.5 |
C6—Fe1—C3 | 153.77 (11) | C12—C13—H13A | 119.5 |
C5—Fe1—C3 | 68.76 (9) | C15—C14—C13 | 119.7 (2) |
C1—Fe1—C9 | 158.57 (10) | C15—C14—H14A | 120.2 |
C7—Fe1—C9 | 68.04 (12) | C13—C14—H14A | 120.2 |
C8—Fe1—C9 | 40.62 (12) | C14—C15—C16 | 119.85 (19) |
C2—Fe1—C9 | 160.10 (10) | C14—C15—H15A | 120.1 |
C6—Fe1—C9 | 68.02 (11) | C16—C15—H15A | 120.1 |
C5—Fe1—C9 | 123.97 (10) | C15—C16—C17 | 121.5 (2) |
C3—Fe1—C9 | 125.55 (11) | C15—C16—H16A | 119.3 |
C1—Fe1—C4 | 69.23 (9) | C17—C16—H16A | 119.3 |
C7—Fe1—C4 | 154.99 (12) | C16—C17—C12 | 118.18 (18) |
C8—Fe1—C4 | 122.09 (12) | C16—C17—P1 | 121.89 (16) |
C2—Fe1—C4 | 68.54 (10) | C12—C17—P1 | 119.88 (14) |
C6—Fe1—C4 | 163.94 (10) | C19—C18—C23 | 118.26 (19) |
C5—Fe1—C4 | 40.98 (8) | C19—C18—P1 | 117.21 (17) |
C3—Fe1—C4 | 40.43 (9) | C23—C18—P1 | 124.51 (15) |
C9—Fe1—C4 | 110.42 (11) | C20—C19—C18 | 121.0 (2) |
C1—Fe1—C10 | 122.04 (9) | C20—C19—H19A | 119.5 |
C7—Fe1—C10 | 67.90 (12) | C18—C19—H19A | 119.5 |
C8—Fe1—C10 | 67.81 (11) | C19—C20—C21 | 120.3 (2) |
C2—Fe1—C10 | 155.54 (10) | C19—C20—H20A | 119.8 |
C6—Fe1—C10 | 40.32 (10) | C21—C20—H20A | 119.8 |
C5—Fe1—C10 | 110.38 (9) | C22—C21—C20 | 119.6 (2) |
C3—Fe1—C10 | 163.54 (10) | C22—C21—H21A | 120.2 |
C9—Fe1—C10 | 40.29 (10) | C20—C21—H21A | 120.2 |
C4—Fe1—C10 | 128.20 (10) | C21—C22—C23 | 120.4 (2) |
C24—P1—C18 | 101.26 (10) | C21—C22—H22A | 119.8 |
C24—P1—C17 | 102.60 (9) | C23—C22—H22A | 119.8 |
C18—P1—C17 | 100.64 (9) | C22—C23—C18 | 120.43 (18) |
C5—P2—C36 | 100.83 (9) | C22—C23—H23A | 119.8 |
C5—P2—C30 | 98.80 (10) | C18—C23—H23A | 119.8 |
C36—P2—C30 | 103.98 (9) | C25—C24—C29 | 118.6 (2) |
C11—O1—H1A | 110 (2) | C25—C24—P1 | 124.09 (18) |
C2—C1—C5 | 107.90 (17) | C29—C24—P1 | 117.28 (18) |
C2—C1—C11 | 126.3 (2) | C24—C25—C26 | 120.8 (3) |
C5—C1—C11 | 125.77 (18) | C24—C25—H25A | 119.6 |
C2—C1—Fe1 | 70.09 (11) | C26—C25—H25A | 119.6 |
C5—C1—Fe1 | 70.06 (11) | C27—C26—C25 | 120.0 (3) |
C11—C1—Fe1 | 125.88 (13) | C27—C26—H26A | 120.0 |
C3—C2—C1 | 108.1 (2) | C25—C26—H26A | 120.0 |
C3—C2—Fe1 | 69.92 (13) | C28—C27—C26 | 119.9 (3) |
C1—C2—Fe1 | 68.82 (11) | C28—C27—H27A | 120.0 |
C3—C2—H2A | 126.0 | C26—C27—H27A | 120.0 |
C1—C2—H2A | 126.0 | C27—C28—C29 | 120.2 (3) |
Fe1—C2—H2A | 126.9 | C27—C28—H28A | 119.9 |
C4—C3—C2 | 108.5 (2) | C29—C28—H28A | 119.9 |
C4—C3—Fe1 | 69.94 (15) | C24—C29—C28 | 120.4 (3) |
C2—C3—Fe1 | 69.38 (14) | C24—C29—H29A | 119.8 |
C4—C3—H3A | 125.7 | C28—C29—H29A | 119.8 |
C2—C3—H3A | 125.7 | C35—C30—C31 | 118.5 (2) |
Fe1—C3—H3A | 126.5 | C35—C30—P2 | 124.53 (16) |
C3—C4—C5 | 108.4 (2) | C31—C30—P2 | 116.88 (17) |
C3—C4—Fe1 | 69.63 (15) | C32—C31—C30 | 120.8 (2) |
C5—C4—Fe1 | 69.30 (12) | C32—C31—H31A | 119.6 |
C3—C4—H4A | 125.8 | C30—C31—H31A | 119.6 |
C5—C4—H4A | 125.8 | C33—C32—C31 | 120.2 (2) |
Fe1—C4—H4A | 126.8 | C33—C32—H32A | 119.9 |
C4—C5—C1 | 107.12 (18) | C31—C32—H32A | 119.9 |
C4—C5—P2 | 127.69 (17) | C32—C33—C34 | 119.5 (2) |
C1—C5—P2 | 125.19 (15) | C32—C33—H33A | 120.2 |
C4—C5—Fe1 | 69.72 (12) | C34—C33—H33A | 120.2 |
C1—C5—Fe1 | 68.39 (11) | C33—C34—C35 | 120.2 (2) |
P2—C5—Fe1 | 126.60 (11) | C33—C34—H34A | 119.9 |
C10—C6—C7 | 107.5 (2) | C35—C34—H34A | 119.9 |
C10—C6—Fe1 | 70.18 (14) | C30—C35—C34 | 120.7 (2) |
C7—C6—Fe1 | 69.01 (16) | C30—C35—H35A | 119.7 |
C10—C6—H6A | 126.2 | C34—C35—H35A | 119.7 |
C7—C6—H6A | 126.2 | C37—C36—C41 | 118.68 (19) |
Fe1—C6—H6A | 126.1 | C37—C36—P2 | 123.54 (16) |
C8—C7—C6 | 108.4 (3) | C41—C36—P2 | 117.47 (16) |
C8—C7—Fe1 | 70.03 (17) | C36—C37—C38 | 120.9 (2) |
C6—C7—Fe1 | 70.37 (15) | C36—C37—H37A | 119.6 |
C8—C7—H7A | 125.8 | C38—C37—H37A | 119.6 |
C6—C7—H7A | 125.8 | C39—C38—C37 | 119.8 (2) |
Fe1—C7—H7A | 125.4 | C39—C38—H38A | 120.1 |
C7—C8—C9 | 108.6 (3) | C37—C38—H38A | 120.1 |
C7—C8—Fe1 | 69.81 (15) | C40—C39—C38 | 120.0 (2) |
C9—C8—Fe1 | 70.43 (15) | C40—C39—H39A | 120.0 |
C7—C8—H8A | 125.7 | C38—C39—H39A | 120.0 |
C9—C8—H8A | 125.7 | C39—C40—C41 | 120.4 (2) |
Fe1—C8—H8A | 125.6 | C39—C40—H40A | 119.8 |
C10—C9—C8 | 107.2 (3) | C41—C40—H40A | 119.8 |
C10—C9—Fe1 | 70.02 (14) | C40—C41—C36 | 120.2 (2) |
C8—C9—Fe1 | 68.95 (16) | C40—C41—H41A | 119.9 |
C10—C9—H9A | 126.4 | C36—C41—H41A | 119.9 |
C7—Fe1—C1—C2 | 74.09 (18) | C2—Fe1—C7—C8 | −123.03 (18) |
C8—Fe1—C1—C2 | 44.9 (3) | C6—Fe1—C7—C8 | 119.1 (3) |
C6—Fe1—C1—C2 | 115.44 (15) | C5—Fe1—C7—C8 | 170.0 (3) |
C5—Fe1—C1—C2 | −118.63 (17) | C3—Fe1—C7—C8 | −81.9 (2) |
C3—Fe1—C1—C2 | −37.34 (14) | C9—Fe1—C7—C8 | 37.71 (18) |
C9—Fe1—C1—C2 | −173.9 (3) | C4—Fe1—C7—C8 | −53.8 (3) |
C4—Fe1—C1—C2 | −80.76 (14) | C10—Fe1—C7—C8 | 81.33 (19) |
C10—Fe1—C1—C2 | 156.36 (14) | C1—Fe1—C7—C6 | 77.20 (18) |
C7—Fe1—C1—C5 | −167.29 (15) | C8—Fe1—C7—C6 | −119.1 (3) |
C8—Fe1—C1—C5 | 163.5 (3) | C2—Fe1—C7—C6 | 117.87 (16) |
C2—Fe1—C1—C5 | 118.63 (17) | C5—Fe1—C7—C6 | 50.9 (4) |
C6—Fe1—C1—C5 | −125.93 (13) | C3—Fe1—C7—C6 | 158.99 (15) |
C3—Fe1—C1—C5 | 81.28 (13) | C9—Fe1—C7—C6 | −81.39 (17) |
C9—Fe1—C1—C5 | −55.3 (3) | C4—Fe1—C7—C6 | −172.8 (2) |
C4—Fe1—C1—C5 | 37.87 (12) | C10—Fe1—C7—C6 | −37.76 (15) |
C10—Fe1—C1—C5 | −85.01 (14) | C6—C7—C8—C9 | 0.2 (3) |
C7—Fe1—C1—C11 | −47.0 (2) | Fe1—C7—C8—C9 | −60.0 (2) |
C8—Fe1—C1—C11 | −76.2 (4) | C6—C7—C8—Fe1 | 60.16 (18) |
C2—Fe1—C1—C11 | −121.0 (2) | C1—Fe1—C8—C7 | 40.0 (4) |
C6—Fe1—C1—C11 | −5.6 (2) | C2—Fe1—C8—C7 | 73.1 (2) |
C5—Fe1—C1—C11 | 120.3 (2) | C6—Fe1—C8—C7 | −37.87 (19) |
C3—Fe1—C1—C11 | −158.4 (2) | C5—Fe1—C8—C7 | −171.0 (3) |
C9—Fe1—C1—C11 | 65.1 (4) | C3—Fe1—C8—C7 | 114.9 (2) |
C4—Fe1—C1—C11 | 158.2 (2) | C9—Fe1—C8—C7 | −119.4 (3) |
C10—Fe1—C1—C11 | 35.3 (2) | C4—Fe1—C8—C7 | 156.26 (18) |
C5—C1—C2—C3 | −1.0 (2) | C10—Fe1—C8—C7 | −81.6 (2) |
C11—C1—C2—C3 | 179.57 (19) | C1—Fe1—C8—C9 | 159.4 (2) |
Fe1—C1—C2—C3 | 59.08 (16) | C7—Fe1—C8—C9 | 119.4 (3) |
C5—C1—C2—Fe1 | −60.13 (13) | C2—Fe1—C8—C9 | −167.49 (16) |
C11—C1—C2—Fe1 | 120.49 (19) | C6—Fe1—C8—C9 | 81.5 (2) |
C1—Fe1—C2—C3 | −119.74 (19) | C5—Fe1—C8—C9 | −51.6 (4) |
C7—Fe1—C2—C3 | 117.71 (17) | C3—Fe1—C8—C9 | −125.72 (19) |
C8—Fe1—C2—C3 | 78.19 (19) | C4—Fe1—C8—C9 | −84.3 (2) |
C6—Fe1—C2—C3 | 158.71 (15) | C10—Fe1—C8—C9 | 37.84 (17) |
C5—Fe1—C2—C3 | −81.22 (15) | C7—C8—C9—C10 | −0.2 (3) |
C9—Fe1—C2—C3 | 53.7 (4) | Fe1—C8—C9—C10 | −59.81 (17) |
C4—Fe1—C2—C3 | −37.14 (14) | C7—C8—C9—Fe1 | 59.61 (19) |
C10—Fe1—C2—C3 | −174.9 (2) | C1—Fe1—C9—C10 | −40.6 (3) |
C7—Fe1—C2—C1 | −122.56 (16) | C7—Fe1—C9—C10 | 81.27 (19) |
C8—Fe1—C2—C1 | −162.07 (16) | C8—Fe1—C9—C10 | 118.6 (3) |
C6—Fe1—C2—C1 | −81.55 (16) | C2—Fe1—C9—C10 | 151.3 (3) |
C5—Fe1—C2—C1 | 38.52 (12) | C6—Fe1—C9—C10 | 37.31 (16) |
C3—Fe1—C2—C1 | 119.74 (19) | C5—Fe1—C9—C10 | −81.64 (17) |
C9—Fe1—C2—C1 | 173.5 (3) | C3—Fe1—C9—C10 | −168.46 (15) |
C4—Fe1—C2—C1 | 82.59 (14) | C4—Fe1—C9—C10 | −125.54 (15) |
C10—Fe1—C2—C1 | −55.2 (3) | C1—Fe1—C9—C8 | −159.1 (3) |
C1—C2—C3—C4 | 0.7 (3) | C7—Fe1—C9—C8 | −37.3 (2) |
Fe1—C2—C3—C4 | 59.15 (18) | C2—Fe1—C9—C8 | 32.7 (4) |
C1—C2—C3—Fe1 | −58.40 (15) | C6—Fe1—C9—C8 | −81.2 (2) |
C1—Fe1—C3—C4 | −82.25 (15) | C5—Fe1—C9—C8 | 159.80 (19) |
C7—Fe1—C3—C4 | 162.08 (16) | C3—Fe1—C9—C8 | 73.0 (2) |
C8—Fe1—C3—C4 | 120.29 (17) | C4—Fe1—C9—C8 | 115.9 (2) |
C2—Fe1—C3—C4 | −120.0 (2) | C10—Fe1—C9—C8 | −118.6 (3) |
C6—Fe1—C3—C4 | −166.0 (2) | C7—C6—C10—C9 | −0.1 (3) |
C5—Fe1—C3—C4 | −37.56 (14) | Fe1—C6—C10—C9 | 59.08 (16) |
C9—Fe1—C3—C4 | 79.76 (18) | C7—C6—C10—Fe1 | −59.14 (17) |
C10—Fe1—C3—C4 | 52.6 (4) | C8—C9—C10—C6 | 0.2 (3) |
C1—Fe1—C3—C2 | 37.70 (13) | Fe1—C9—C10—C6 | −58.97 (16) |
C7—Fe1—C3—C2 | −77.97 (17) | C8—C9—C10—Fe1 | 59.13 (19) |
C8—Fe1—C3—C2 | −119.76 (16) | C1—Fe1—C10—C6 | −76.58 (17) |
C6—Fe1—C3—C2 | −46.1 (3) | C7—Fe1—C10—C6 | 38.04 (17) |
C5—Fe1—C3—C2 | 82.39 (14) | C8—Fe1—C10—C6 | 81.55 (19) |
C9—Fe1—C3—C2 | −160.29 (14) | C2—Fe1—C10—C6 | −37.0 (3) |
C4—Fe1—C3—C2 | 120.0 (2) | C5—Fe1—C10—C6 | −121.39 (15) |
C10—Fe1—C3—C2 | 172.5 (3) | C3—Fe1—C10—C6 | 154.8 (3) |
C2—C3—C4—C5 | −0.2 (3) | C9—Fe1—C10—C6 | 119.7 (2) |
Fe1—C3—C4—C5 | 58.64 (16) | C4—Fe1—C10—C6 | −164.29 (15) |
C2—C3—C4—Fe1 | −58.80 (18) | C1—Fe1—C10—C9 | 163.73 (15) |
C1—Fe1—C4—C3 | 81.58 (16) | C7—Fe1—C10—C9 | −81.66 (19) |
C7—Fe1—C4—C3 | −39.7 (3) | C8—Fe1—C10—C9 | −38.14 (18) |
C8—Fe1—C4—C3 | −77.59 (19) | C2—Fe1—C10—C9 | −156.7 (2) |
C2—Fe1—C4—C3 | 37.38 (14) | C6—Fe1—C10—C9 | −119.7 (2) |
C6—Fe1—C4—C3 | 157.3 (3) | C5—Fe1—C10—C9 | 118.92 (16) |
C5—Fe1—C4—C3 | 120.0 (2) | C3—Fe1—C10—C9 | 35.1 (4) |
C9—Fe1—C4—C3 | −121.32 (16) | C4—Fe1—C10—C9 | 76.01 (18) |
C10—Fe1—C4—C3 | −163.36 (15) | C2—C1—C11—O1 | −25.1 (3) |
C1—Fe1—C4—C5 | −38.37 (12) | C5—C1—C11—O1 | 155.63 (18) |
C7—Fe1—C4—C5 | −159.7 (2) | Fe1—C1—C11—O1 | 65.5 (2) |
C8—Fe1—C4—C5 | 162.46 (15) | C2—C1—C11—C12 | 96.6 (2) |
C2—Fe1—C4—C5 | −82.57 (14) | C5—C1—C11—C12 | −82.7 (2) |
C6—Fe1—C4—C5 | 37.4 (4) | Fe1—C1—C11—C12 | −172.79 (14) |
C3—Fe1—C4—C5 | −120.0 (2) | O1—C11—C12—C13 | 68.2 (2) |
C9—Fe1—C4—C5 | 118.72 (14) | C1—C11—C12—C13 | −51.7 (3) |
C10—Fe1—C4—C5 | 76.69 (16) | O1—C11—C12—C17 | −110.6 (2) |
C3—C4—C5—C1 | −0.5 (3) | C1—C11—C12—C17 | 129.5 (2) |
Fe1—C4—C5—C1 | 58.36 (13) | C17—C12—C13—C14 | −1.1 (3) |
C3—C4—C5—P2 | 179.97 (17) | C11—C12—C13—C14 | −179.9 (2) |
Fe1—C4—C5—P2 | −121.18 (17) | C12—C13—C14—C15 | −1.4 (4) |
C3—C4—C5—Fe1 | −58.85 (18) | C13—C14—C15—C16 | 1.8 (4) |
C2—C1—C5—C4 | 0.9 (2) | C14—C15—C16—C17 | 0.1 (3) |
C11—C1—C5—C4 | −179.67 (18) | C15—C16—C17—C12 | −2.5 (3) |
Fe1—C1—C5—C4 | −59.20 (14) | C15—C16—C17—P1 | −179.75 (17) |
C2—C1—C5—P2 | −179.50 (16) | C13—C12—C17—C16 | 3.0 (3) |
C11—C1—C5—P2 | −0.1 (3) | C11—C12—C17—C16 | −178.27 (18) |
Fe1—C1—C5—P2 | 120.36 (16) | C13—C12—C17—P1 | −179.75 (16) |
C2—C1—C5—Fe1 | 60.14 (13) | C11—C12—C17—P1 | −1.0 (3) |
C11—C1—C5—Fe1 | −120.47 (18) | C24—P1—C17—C16 | −11.30 (19) |
C36—P2—C5—C4 | −98.5 (2) | C18—P1—C17—C16 | −115.52 (17) |
C30—P2—C5—C4 | 7.7 (2) | C24—P1—C17—C12 | 171.52 (16) |
C36—P2—C5—C1 | 82.08 (18) | C18—P1—C17—C12 | 67.30 (17) |
C30—P2—C5—C1 | −171.75 (17) | C24—P1—C18—C19 | 95.15 (18) |
C36—P2—C5—Fe1 | 169.93 (13) | C17—P1—C18—C19 | −159.55 (17) |
C30—P2—C5—Fe1 | −83.90 (14) | C24—P1—C18—C23 | −86.39 (19) |
C1—Fe1—C5—C4 | 118.94 (17) | C17—P1—C18—C23 | 18.90 (19) |
C7—Fe1—C5—C4 | 153.5 (3) | C23—C18—C19—C20 | −0.6 (3) |
C8—Fe1—C5—C4 | −44.3 (3) | P1—C18—C19—C20 | 177.94 (18) |
C2—Fe1—C5—C4 | 80.82 (14) | C18—C19—C20—C21 | −0.8 (4) |
C6—Fe1—C5—C4 | −168.09 (14) | C19—C20—C21—C22 | 1.3 (4) |
C3—Fe1—C5—C4 | 37.08 (14) | C20—C21—C22—C23 | −0.5 (4) |
C9—Fe1—C5—C4 | −82.29 (16) | C21—C22—C23—C18 | −1.0 (3) |
C10—Fe1—C5—C4 | −125.33 (14) | C19—C18—C23—C22 | 1.5 (3) |
C7—Fe1—C5—C1 | 34.6 (4) | P1—C18—C23—C22 | −176.96 (16) |
C8—Fe1—C5—C1 | −163.3 (3) | C18—P1—C24—C25 | 23.5 (2) |
C2—Fe1—C5—C1 | −38.12 (12) | C17—P1—C24—C25 | −80.3 (2) |
C6—Fe1—C5—C1 | 72.98 (15) | C18—P1—C24—C29 | −154.66 (17) |
C3—Fe1—C5—C1 | −81.86 (13) | C17—P1—C24—C29 | 101.60 (18) |
C9—Fe1—C5—C1 | 158.78 (13) | C29—C24—C25—C26 | 0.4 (4) |
C4—Fe1—C5—C1 | −118.94 (17) | P1—C24—C25—C26 | −177.7 (2) |
C10—Fe1—C5—C1 | 115.73 (13) | C24—C25—C26—C27 | −0.6 (4) |
C1—Fe1—C5—P2 | −118.55 (19) | C25—C26—C27—C28 | −0.3 (4) |
C7—Fe1—C5—P2 | −84.0 (4) | C26—C27—C28—C29 | 1.4 (4) |
C8—Fe1—C5—P2 | 78.2 (3) | C25—C24—C29—C28 | 0.7 (3) |
C2—Fe1—C5—P2 | −156.66 (18) | P1—C24—C29—C28 | 178.92 (19) |
C6—Fe1—C5—P2 | −45.57 (19) | C27—C28—C29—C24 | −1.6 (4) |
C3—Fe1—C5—P2 | 159.59 (17) | C5—P2—C30—C35 | −87.0 (2) |
C9—Fe1—C5—P2 | 40.23 (18) | C36—P2—C30—C35 | 16.6 (2) |
C4—Fe1—C5—P2 | 122.5 (2) | C5—P2—C30—C31 | 89.93 (18) |
C10—Fe1—C5—P2 | −2.82 (17) | C36—P2—C30—C31 | −166.51 (17) |
C1—Fe1—C6—C10 | 120.89 (14) | C35—C30—C31—C32 | 2.1 (3) |
C7—Fe1—C6—C10 | −118.7 (2) | P2—C30—C31—C32 | −174.96 (19) |
C8—Fe1—C6—C10 | −81.27 (17) | C30—C31—C32—C33 | −1.4 (4) |
C2—Fe1—C6—C10 | 163.48 (14) | C31—C32—C33—C34 | 0.1 (4) |
C5—Fe1—C6—C10 | 79.59 (16) | C32—C33—C34—C35 | 0.4 (4) |
C3—Fe1—C6—C10 | −164.1 (2) | C31—C30—C35—C34 | −1.6 (4) |
C9—Fe1—C6—C10 | −37.29 (15) | P2—C30—C35—C34 | 175.2 (2) |
C4—Fe1—C6—C10 | 50.3 (4) | C33—C34—C35—C30 | 0.4 (4) |
C1—Fe1—C6—C7 | −120.38 (17) | C5—P2—C36—C37 | 14.0 (2) |
C8—Fe1—C6—C7 | 37.46 (18) | C30—P2—C36—C37 | −88.04 (19) |
C2—Fe1—C6—C7 | −77.79 (18) | C5—P2—C36—C41 | −159.45 (16) |
C5—Fe1—C6—C7 | −161.68 (16) | C30—P2—C36—C41 | 98.54 (17) |
C3—Fe1—C6—C7 | −45.4 (3) | C41—C36—C37—C38 | 0.3 (3) |
C9—Fe1—C6—C7 | 81.44 (18) | P2—C36—C37—C38 | −173.05 (17) |
C4—Fe1—C6—C7 | 169.0 (3) | C36—C37—C38—C39 | −0.5 (3) |
C10—Fe1—C6—C7 | 118.7 (2) | C37—C38—C39—C40 | 0.2 (3) |
C10—C6—C7—C8 | −0.1 (3) | C38—C39—C40—C41 | 0.3 (4) |
Fe1—C6—C7—C8 | −59.9 (2) | C39—C40—C41—C36 | −0.6 (3) |
C10—C6—C7—Fe1 | 59.88 (16) | C37—C36—C41—C40 | 0.3 (3) |
C1—Fe1—C7—C8 | −163.71 (16) | P2—C36—C41—C40 | 174.00 (17) |
D—H···A | D—H | H···A | D···A | D—H···A |
C11—H11A···P1 | 1.00 | 2.56 | 3.153 (2) | 118 |
O1—H1A···C23 | 0.78 (3) | 2.51 (3) | 3.217 (3) | 152 (2) |
Experimental details
Crystal data | |
Chemical formula | [Fe(C5H5)(C36H29OP2)] |
Mr | 660.47 |
Crystal system, space group | Monoclinic, P21 |
Temperature (K) | 162 |
a, b, c (Å) | 11.6111 (15), 8.6154 (10), 16.481 (2) |
β (°) | 97.807 (12) |
V (Å3) | 1633.4 (3) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.59 |
Crystal size (mm) | 0.40 × 0.40 × 0.32 |
Data collection | |
Diffractometer | Siemens SMART 1K CCD diffractometer |
Absorption correction | Numerical (SHELXTL; Sheldrick, 2008) |
Tmin, Tmax | 0.795, 0.845 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 25293, 9131, 7926 |
Rint | 0.051 |
(sin θ/λ)max (Å−1) | 0.714 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.038, 0.083, 1.07 |
No. of reflections | 9131 |
No. of parameters | 410 |
No. of restraints | 1 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.33, −0.23 |
Absolute structure | Flack (1983), 4069 Friedel pairs |
Absolute structure parameter | −0.023 (10) |
Computer programs: SMART (Siemens, 1995), SAINT (Siemens, 1995), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).
D—H···A | D—H | H···A | D···A | D—H···A |
C11—H11A···P1 | 1.00 | 2.56 | 3.153 (2) | 118 |
O1—H1A···C23 | 0.78 (3) | 2.51 (3) | 3.217 (3) | 152 (2) |
The structure originally published for the Taniaphos ligands, a chiral ligand technology owned by Umicore and sold via Solvias, recently had to be corrected. It was shown that these ligands do not have the (R,Sp) or (S,Rp) but the (R,Rp) or (S,Sp) configuration, respectively (Fukuzawa, Yamamoto, Hosaka & Kikuchi, et al., 2007; Ireland et al., 2008). The planar chirality of the 1,2-disubstituted ferrocene initially had been assigned incorrectly. Our present investigation confirms the configuration of a special member of this family, bearing a hydroxy group in the side-chain of the ferrocene ring (Lotz & Spindler, 2005).
The molecular structure of the title compound is shown in Fig. 1. The ferrocene group deviates only 4° from an eclipsed conformation. The angle between the planes of the two cyclopentadienyl rings is 4.2 (2)°. Both P atoms have a pyramidal conformation. The lone-pair lobe of atom P1 shows a short intramolecular contact distance of 2.56 Å with the H atom of C11 (Table 1). The hydroxy group is not involved in conventional inter- or intramolecular hydrogen bonding. It shows instead a short intramolecular O—H···πphenyl interaction with the phenyl ring labeled C18 through C23. The O—H group is not directed to the center of this phenyl ring, but points mainly to atom C23 (Table 1). There is an intramolecular π···π interaction between the benzene rings labeled C12 → C17 and C36 → C41. The angle between the planes of these rings is 4.8 (2)°. The shortest contact distance is 3.498 (3)Å between C12 and C37. The crystal packing shows five very weak intermolecular C—H···π interactions, with H···Cg distances between 3.26 and 3.39 Å (Cg is the centroid of a phenyl or cyclopentadienyl ring).