In the molecular structure of 5-ferrocenyl-5-methyltetrahydrofuran-2-one, [Fe(C
5H
5)(C
10H
11O
2)], the five-membered heterocyclic ring adopts a distorted envelope conformation. The ferrocenyl substituent is in an equatorial position with respect to this ring. In the crystal structure, there are close C—H
O and C—H
π intermolecular contacts.
Supporting information
CCDC reference: 270471
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.009 Å
- R factor = 0.049
- wR factor = 0.127
- Data-to-parameter ratio = 13.7
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT199_ALERT_1_C Check the Reported cell_measurement_temperature 293
PLAT200_ALERT_1_C Check the Reported cell_ambient_temperature .... 293
PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C7
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for Fe1
PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 9
PLAT480_ALERT_4_C Long H...A H-Bond Reported H14A .. CG1 .. 2.89 Ang.
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 67.98
From the CIF: _reflns_number_total 2253
Count of symmetry unique reflns 1208
Completeness (_total/calc) 186.51%
TEST3: Check Friedels for noncentro structure
Estimate of Friedel pairs measured 1045
Fraction of Friedel pairs measured 0.865
Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
6 ALERT level C = Check and explain
1 ALERT level G = General alerts; check
2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
2 ALERT type 2 Indicator that the structure model may be wrong or deficient
1 ALERT type 3 Indicator that the structure quality may be low
2 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation,
1989); cell refinement: MSC/AFC Diffractometer Control Software; data reduction: TEXSAN (Molecular Structure Corporation, 1989); program(s) used to solve structure: SHELXS86 (Sheldrick, 1985); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 1998); software used to prepare material for publication: SHELXL97, WinGX (Farrugia, 1999) and PARST97 (Nardelli, 1996).
5-Ferrocenyl-5-methyltetrahydrofuran-2-one
top
Crystal data top
[Fe(C5H5)(C10H11O2)] | F(000) = 296 |
Mr = 284.13 | Dx = 1.487 Mg m−3 |
Monoclinic, P21 | Cu Kα radiation, λ = 1.54178 Å |
Hall symbol: P 2yb | Cell parameters from 25 reflections |
a = 5.8067 (10) Å | θ = 34.9–38.2° |
b = 12.7007 (14) Å | µ = 9.45 mm−1 |
c = 8.7274 (7) Å | T = 293 K |
β = 99.643 (14)° | Block, orange |
V = 634.54 (14) Å3 | 0.35 × 0.25 × 0.25 mm |
Z = 2 | |
Data collection top
Rigaku AFC-5S diffractometer | 1856 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.065 |
Graphite monochromator | θmax = 68.0°, θmin = 5.1° |
ω scans | h = −6→6 |
Absorption correction: analytical (de Meulenaer & Tompa, 1965) | k = −14→15 |
Tmin = 0.137, Tmax = 0.201 | l = −10→10 |
4444 measured reflections | 3 standard reflections every 150 reflections |
2253 independent reflections | intensity decay: 1.2% |
Refinement top
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.049 | w = 1/[σ2(Fo2) + (0.0506P)2 + 0.5135P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.127 | (Δ/σ)max < 0.001 |
S = 1.09 | Δρmax = 0.35 e Å−3 |
2253 reflections | Δρmin = −0.50 e Å−3 |
165 parameters | Extinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
1 restraint | Extinction coefficient: 0.0053 (8) |
Primary atom site location: structure-invariant direct methods | Absolute structure: Flack (1983), with 1045 Friedel pairs |
Secondary atom site location: difference Fourier map | Absolute structure parameter: −0.011 (9) |
Special details top
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
Fe1 | 0.85951 (11) | 0.59955 (6) | 0.88365 (7) | 0.0435 (3) | |
C1 | 0.6700 (8) | 0.5896 (6) | 0.6642 (5) | 0.0430 (12) | |
C2 | 0.5448 (10) | 0.6467 (5) | 0.7650 (6) | 0.0495 (14) | |
H2 | 0.3991 | 0.6291 | 0.7884 | 0.059* | |
C3 | 0.6818 (11) | 0.7348 (5) | 0.8232 (7) | 0.0588 (16) | |
H3 | 0.6421 | 0.7848 | 0.8921 | 0.071* | |
C4 | 0.8875 (12) | 0.7338 (6) | 0.7590 (7) | 0.0639 (17) | |
H4 | 1.0061 | 0.7837 | 0.7768 | 0.077* | |
C5 | 0.8844 (10) | 0.6440 (4) | 0.6627 (6) | 0.0481 (14) | |
H5 | 1.0017 | 0.6240 | 0.6080 | 0.058* | |
C6 | 0.9101 (12) | 0.4517 (6) | 0.9753 (7) | 0.0666 (18) | |
H6 | 0.8522 | 0.3898 | 0.9264 | 0.080* | |
C7 | 0.7965 (12) | 0.5154 (7) | 1.0707 (7) | 0.076 (2) | |
H7 | 0.6499 | 0.5023 | 1.0961 | 0.092* | |
C8 | 0.9374 (10) | 0.6014 (9) | 1.1212 (5) | 0.0732 (19) | |
H8 | 0.9019 | 0.6555 | 1.1852 | 0.088* | |
C9 | 1.1453 (9) | 0.5912 (8) | 1.0572 (6) | 0.0648 (16) | |
H9 | 1.2711 | 0.6375 | 1.0720 | 0.078* | |
C10 | 1.1274 (11) | 0.4984 (6) | 0.9668 (7) | 0.0588 (17) | |
H10 | 1.2393 | 0.4727 | 0.9116 | 0.071* | |
C11 | 0.5886 (9) | 0.4956 (4) | 0.5700 (6) | 0.0433 (13) | |
O12 | 0.4430 (7) | 0.4335 (3) | 0.6615 (4) | 0.0539 (10) | |
C13 | 0.5010 (13) | 0.3314 (5) | 0.6650 (7) | 0.0649 (17) | |
C14 | 0.6896 (12) | 0.3112 (5) | 0.5729 (8) | 0.0690 (18) | |
H14A | 0.6277 | 0.2774 | 0.4750 | 0.083* | |
H14B | 0.8099 | 0.2666 | 0.6301 | 0.083* | |
C15 | 0.7859 (11) | 0.4186 (5) | 0.5458 (7) | 0.0575 (15) | |
H15A | 0.8207 | 0.4243 | 0.4413 | 0.069* | |
H15B | 0.9271 | 0.4326 | 0.6195 | 0.069* | |
O13 | 0.4021 (11) | 0.2702 (4) | 0.7374 (7) | 0.107 (2) | |
C16 | 0.4328 (11) | 0.5242 (6) | 0.4184 (6) | 0.0595 (16) | |
H16A | 0.3039 | 0.5658 | 0.4398 | 0.089* | |
H16B | 0.3749 | 0.4611 | 0.3649 | 0.089* | |
H16C | 0.5211 | 0.5638 | 0.3546 | 0.089* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Fe1 | 0.0407 (4) | 0.0601 (5) | 0.0258 (3) | 0.0042 (5) | −0.0060 (2) | −0.0019 (5) |
C1 | 0.046 (3) | 0.055 (3) | 0.0238 (18) | 0.004 (3) | −0.0058 (18) | 0.001 (3) |
C2 | 0.049 (3) | 0.060 (4) | 0.035 (3) | 0.005 (3) | −0.007 (2) | 0.002 (2) |
C3 | 0.071 (4) | 0.051 (4) | 0.045 (3) | 0.010 (3) | −0.017 (3) | −0.014 (3) |
C4 | 0.068 (4) | 0.071 (4) | 0.046 (3) | −0.012 (4) | −0.013 (3) | −0.003 (3) |
C5 | 0.051 (3) | 0.060 (4) | 0.031 (2) | −0.008 (3) | 0.000 (2) | −0.003 (2) |
C6 | 0.070 (4) | 0.079 (5) | 0.043 (3) | 0.002 (4) | −0.014 (3) | 0.013 (3) |
C7 | 0.050 (4) | 0.141 (7) | 0.036 (3) | 0.017 (4) | 0.000 (3) | 0.028 (4) |
C8 | 0.064 (4) | 0.123 (6) | 0.028 (2) | 0.025 (6) | −0.007 (2) | −0.006 (5) |
C9 | 0.047 (3) | 0.096 (5) | 0.043 (2) | −0.001 (5) | −0.016 (2) | 0.004 (5) |
C10 | 0.052 (4) | 0.079 (5) | 0.041 (3) | 0.022 (3) | −0.004 (3) | −0.001 (3) |
C11 | 0.047 (3) | 0.048 (3) | 0.032 (2) | 0.000 (3) | −0.001 (2) | 0.003 (2) |
O12 | 0.057 (2) | 0.057 (3) | 0.048 (2) | −0.007 (2) | 0.0088 (18) | 0.0015 (19) |
C13 | 0.090 (5) | 0.052 (4) | 0.052 (3) | −0.006 (4) | 0.006 (3) | 0.004 (3) |
C14 | 0.081 (5) | 0.059 (4) | 0.064 (4) | 0.003 (4) | 0.001 (4) | −0.006 (3) |
C15 | 0.064 (4) | 0.060 (4) | 0.047 (3) | 0.001 (3) | 0.006 (3) | −0.007 (3) |
O13 | 0.145 (5) | 0.076 (4) | 0.107 (4) | −0.024 (4) | 0.042 (4) | 0.017 (3) |
C16 | 0.072 (4) | 0.066 (4) | 0.033 (3) | −0.010 (3) | −0.011 (3) | −0.003 (3) |
Geometric parameters (Å, º) top
Fe1—C3 | 2.028 (6) | C6—H6 | 0.9300 |
Fe1—C2 | 2.034 (5) | C7—C8 | 1.391 (12) |
Fe1—C7 | 2.035 (6) | C7—H7 | 0.9300 |
Fe1—C5 | 2.037 (5) | C8—C9 | 1.418 (8) |
Fe1—C6 | 2.042 (7) | C8—H8 | 0.9300 |
Fe1—C4 | 2.043 (7) | C9—C10 | 1.413 (11) |
Fe1—C1 | 2.047 (4) | C9—H9 | 0.9300 |
Fe1—C8 | 2.047 (5) | C10—H10 | 0.9300 |
Fe1—C9 | 2.053 (5) | C11—O12 | 1.483 (6) |
Fe1—C10 | 2.054 (6) | C11—C16 | 1.517 (7) |
C1—C5 | 1.426 (8) | C11—C15 | 1.547 (8) |
C1—C2 | 1.429 (8) | O12—C13 | 1.339 (7) |
C1—C11 | 1.481 (9) | C13—O13 | 1.206 (8) |
C2—C3 | 1.417 (9) | C13—C14 | 1.486 (10) |
C2—H2 | 0.9300 | C14—C15 | 1.508 (9) |
C3—C4 | 1.401 (9) | C14—H14A | 0.9700 |
C3—H3 | 0.9300 | C14—H14B | 0.9700 |
C4—C5 | 1.415 (9) | C15—H15A | 0.9700 |
C4—H4 | 0.9300 | C15—H15B | 0.9700 |
C5—H5 | 0.9300 | C16—H16A | 0.9600 |
C6—C7 | 1.402 (10) | C16—H16B | 0.9600 |
C6—C10 | 1.407 (9) | C16—H16C | 0.9600 |
| | | |
C3—Fe1—C2 | 40.8 (2) | C5—C4—H4 | 125.7 |
C3—Fe1—C7 | 120.1 (3) | Fe1—C4—H4 | 127.1 |
C2—Fe1—C7 | 107.2 (3) | C4—C5—C1 | 108.0 (5) |
C3—Fe1—C5 | 68.4 (2) | C4—C5—Fe1 | 69.9 (3) |
C2—Fe1—C5 | 68.7 (2) | C1—C5—Fe1 | 69.9 (3) |
C7—Fe1—C5 | 162.8 (3) | C4—C5—H5 | 126.0 |
C3—Fe1—C6 | 156.1 (3) | C1—C5—H5 | 126.0 |
C2—Fe1—C6 | 121.9 (3) | Fe1—C5—H5 | 125.7 |
C7—Fe1—C6 | 40.2 (3) | C7—C6—C10 | 107.7 (7) |
C5—Fe1—C6 | 126.6 (3) | C7—C6—Fe1 | 69.6 (4) |
C3—Fe1—C4 | 40.3 (3) | C10—C6—Fe1 | 70.4 (4) |
C2—Fe1—C4 | 68.2 (2) | C7—C6—H6 | 126.2 |
C7—Fe1—C4 | 155.0 (3) | C10—C6—H6 | 126.2 |
C5—Fe1—C4 | 40.6 (2) | Fe1—C6—H6 | 125.5 |
C6—Fe1—C4 | 163.0 (3) | C8—C7—C6 | 109.3 (6) |
C3—Fe1—C1 | 68.8 (3) | C8—C7—Fe1 | 70.6 (4) |
C2—Fe1—C1 | 41.0 (2) | C6—C7—Fe1 | 70.2 (4) |
C7—Fe1—C1 | 125.3 (3) | C8—C7—H7 | 125.3 |
C5—Fe1—C1 | 40.9 (2) | C6—C7—H7 | 125.3 |
C6—Fe1—C1 | 109.2 (3) | Fe1—C7—H7 | 125.5 |
C4—Fe1—C1 | 68.4 (3) | C7—C8—C9 | 107.3 (8) |
C3—Fe1—C8 | 105.7 (3) | C7—C8—Fe1 | 69.6 (3) |
C2—Fe1—C8 | 122.7 (2) | C9—C8—Fe1 | 70.0 (3) |
C7—Fe1—C8 | 39.9 (3) | C7—C8—H8 | 126.3 |
C5—Fe1—C8 | 156.5 (3) | C9—C8—H8 | 126.3 |
C6—Fe1—C8 | 67.7 (4) | Fe1—C8—H8 | 125.7 |
C4—Fe1—C8 | 120.4 (4) | C10—C9—C8 | 107.9 (7) |
C1—Fe1—C8 | 160.3 (2) | C10—C9—Fe1 | 69.9 (3) |
C3—Fe1—C9 | 123.3 (3) | C8—C9—Fe1 | 69.5 (3) |
C2—Fe1—C9 | 159.5 (3) | C10—C9—H9 | 126.0 |
C7—Fe1—C9 | 67.2 (3) | C8—C9—H9 | 126.0 |
C5—Fe1—C9 | 122.4 (2) | Fe1—C9—H9 | 126.1 |
C6—Fe1—C9 | 67.6 (3) | C6—C10—C9 | 107.7 (6) |
C4—Fe1—C9 | 108.0 (3) | C6—C10—Fe1 | 69.5 (4) |
C1—Fe1—C9 | 158.2 (2) | C9—C10—Fe1 | 69.8 (3) |
C8—Fe1—C9 | 40.5 (2) | C6—C10—H10 | 126.1 |
C3—Fe1—C10 | 160.8 (3) | C9—C10—H10 | 126.1 |
C2—Fe1—C10 | 157.9 (3) | Fe1—C10—H10 | 126.1 |
C7—Fe1—C10 | 67.4 (3) | C1—C11—O12 | 106.7 (4) |
C5—Fe1—C10 | 109.8 (2) | C1—C11—C16 | 112.3 (5) |
C6—Fe1—C10 | 40.2 (3) | O12—C11—C16 | 106.7 (4) |
C4—Fe1—C10 | 125.9 (3) | C1—C11—C15 | 114.2 (5) |
C1—Fe1—C10 | 123.3 (2) | O12—C11—C15 | 103.9 (4) |
C8—Fe1—C10 | 67.9 (3) | C16—C11—C15 | 112.3 (5) |
C9—Fe1—C10 | 40.2 (3) | C13—O12—C11 | 111.3 (5) |
C5—C1—C2 | 107.1 (5) | O13—C13—O12 | 119.8 (7) |
C5—C1—C11 | 125.7 (5) | O13—C13—C14 | 129.1 (7) |
C2—C1—C11 | 127.1 (5) | O12—C13—C14 | 111.1 (6) |
C5—C1—Fe1 | 69.2 (3) | C13—C14—C15 | 104.8 (5) |
C2—C1—Fe1 | 69.0 (3) | C13—C14—H14A | 110.8 |
C11—C1—Fe1 | 129.8 (4) | C15—C14—H14A | 110.8 |
C3—C2—C1 | 107.9 (5) | C13—C14—H14B | 110.8 |
C3—C2—Fe1 | 69.4 (3) | C15—C14—H14B | 110.8 |
C1—C2—Fe1 | 70.0 (3) | H14A—C14—H14B | 108.9 |
C3—C2—H2 | 126.0 | C14—C15—C11 | 104.4 (5) |
C1—C2—H2 | 126.0 | C14—C15—H15A | 110.9 |
Fe1—C2—H2 | 126.2 | C11—C15—H15A | 110.9 |
C4—C3—C2 | 108.4 (6) | C14—C15—H15B | 110.9 |
C4—C3—Fe1 | 70.5 (4) | C11—C15—H15B | 110.9 |
C2—C3—Fe1 | 69.8 (3) | H15A—C15—H15B | 108.9 |
C4—C3—H3 | 125.8 | C11—C16—H16A | 109.5 |
C2—C3—H3 | 125.8 | C11—C16—H16B | 109.5 |
Fe1—C3—H3 | 125.5 | H16A—C16—H16B | 109.5 |
C3—C4—C5 | 108.5 (6) | C11—C16—H16C | 109.5 |
C3—C4—Fe1 | 69.3 (4) | H16A—C16—H16C | 109.5 |
C5—C4—Fe1 | 69.5 (4) | H16B—C16—H16C | 109.5 |
C3—C4—H4 | 125.7 | | |
| | | |
C3—Fe1—C1—C5 | 81.1 (4) | C1—Fe1—C6—C7 | −122.3 (4) |
C2—Fe1—C1—C5 | 118.9 (6) | C8—Fe1—C6—C7 | 36.9 (4) |
C7—Fe1—C1—C5 | −166.2 (4) | C9—Fe1—C6—C7 | 80.8 (4) |
C6—Fe1—C1—C5 | −124.3 (4) | C10—Fe1—C6—C7 | 118.5 (6) |
C4—Fe1—C1—C5 | 37.8 (4) | C3—Fe1—C6—C10 | −159.9 (5) |
C8—Fe1—C1—C5 | 158.3 (11) | C2—Fe1—C6—C10 | 162.8 (3) |
C9—Fe1—C1—C5 | −46.8 (11) | C7—Fe1—C6—C10 | −118.5 (6) |
C10—Fe1—C1—C5 | −81.9 (5) | C5—Fe1—C6—C10 | 76.8 (4) |
C3—Fe1—C1—C2 | −37.8 (4) | C4—Fe1—C6—C10 | 40.3 (10) |
C7—Fe1—C1—C2 | 74.9 (5) | C1—Fe1—C6—C10 | 119.2 (4) |
C5—Fe1—C1—C2 | −118.9 (6) | C8—Fe1—C6—C10 | −81.6 (4) |
C6—Fe1—C1—C2 | 116.8 (4) | C9—Fe1—C6—C10 | −37.7 (4) |
C4—Fe1—C1—C2 | −81.2 (4) | C10—C6—C7—C8 | 0.4 (7) |
C8—Fe1—C1—C2 | 39.4 (13) | Fe1—C6—C7—C8 | −59.9 (5) |
C9—Fe1—C1—C2 | −165.7 (9) | C10—C6—C7—Fe1 | 60.3 (4) |
C10—Fe1—C1—C2 | 159.2 (4) | C3—Fe1—C7—C8 | −78.1 (4) |
C3—Fe1—C1—C11 | −159.1 (6) | C2—Fe1—C7—C8 | −120.7 (4) |
C2—Fe1—C1—C11 | −121.3 (6) | C5—Fe1—C7—C8 | 165.9 (8) |
C7—Fe1—C1—C11 | −46.5 (6) | C6—Fe1—C7—C8 | 120.0 (6) |
C5—Fe1—C1—C11 | 119.7 (6) | C4—Fe1—C7—C8 | −45.5 (7) |
C6—Fe1—C1—C11 | −4.5 (5) | C1—Fe1—C7—C8 | −162.2 (4) |
C4—Fe1—C1—C11 | 157.5 (5) | C9—Fe1—C7—C8 | 38.3 (5) |
C8—Fe1—C1—C11 | −82.0 (13) | C10—Fe1—C7—C8 | 82.1 (4) |
C9—Fe1—C1—C11 | 72.9 (11) | C3—Fe1—C7—C6 | 161.9 (4) |
C10—Fe1—C1—C11 | 37.8 (6) | C2—Fe1—C7—C6 | 119.3 (4) |
C5—C1—C2—C3 | 0.3 (6) | C5—Fe1—C7—C6 | 45.9 (10) |
C11—C1—C2—C3 | −176.1 (5) | C4—Fe1—C7—C6 | −165.5 (5) |
Fe1—C1—C2—C3 | 59.2 (4) | C1—Fe1—C7—C6 | 77.8 (4) |
C5—C1—C2—Fe1 | −58.9 (3) | C8—Fe1—C7—C6 | −120.0 (6) |
C11—C1—C2—Fe1 | 124.7 (6) | C9—Fe1—C7—C6 | −81.7 (5) |
C7—Fe1—C2—C3 | 116.4 (4) | C10—Fe1—C7—C6 | −37.9 (4) |
C5—Fe1—C2—C3 | −81.3 (4) | C6—C7—C8—C9 | −0.4 (7) |
C6—Fe1—C2—C3 | 158.0 (4) | Fe1—C7—C8—C9 | −60.1 (4) |
C4—Fe1—C2—C3 | −37.5 (4) | C6—C7—C8—Fe1 | 59.7 (4) |
C1—Fe1—C2—C3 | −119.2 (5) | C3—Fe1—C8—C7 | 118.5 (4) |
C8—Fe1—C2—C3 | 75.5 (5) | C2—Fe1—C8—C7 | 77.3 (5) |
C9—Fe1—C2—C3 | 45.6 (10) | C5—Fe1—C8—C7 | −169.6 (6) |
C10—Fe1—C2—C3 | −171.5 (6) | C6—Fe1—C8—C7 | −37.2 (4) |
C3—Fe1—C2—C1 | 119.2 (5) | C4—Fe1—C8—C7 | 159.5 (4) |
C7—Fe1—C2—C1 | −124.4 (4) | C1—Fe1—C8—C7 | 47.7 (13) |
C5—Fe1—C2—C1 | 37.9 (4) | C9—Fe1—C8—C7 | −118.3 (8) |
C6—Fe1—C2—C1 | −82.9 (4) | C10—Fe1—C8—C7 | −80.7 (5) |
C4—Fe1—C2—C1 | 81.7 (4) | C3—Fe1—C8—C9 | −123.3 (6) |
C8—Fe1—C2—C1 | −165.3 (5) | C2—Fe1—C8—C9 | −164.4 (5) |
C9—Fe1—C2—C1 | 164.8 (8) | C7—Fe1—C8—C9 | 118.3 (8) |
C10—Fe1—C2—C1 | −52.3 (8) | C5—Fe1—C8—C9 | −51.3 (11) |
C1—C2—C3—C4 | 0.6 (6) | C6—Fe1—C8—C9 | 81.1 (6) |
Fe1—C2—C3—C4 | 60.2 (4) | C4—Fe1—C8—C9 | −82.2 (7) |
C1—C2—C3—Fe1 | −59.6 (4) | C1—Fe1—C8—C9 | 165.9 (10) |
C2—Fe1—C3—C4 | −119.1 (5) | C10—Fe1—C8—C9 | 37.5 (6) |
C7—Fe1—C3—C4 | 159.4 (4) | C7—C8—C9—C10 | 0.3 (7) |
C5—Fe1—C3—C4 | −37.2 (3) | Fe1—C8—C9—C10 | −59.6 (4) |
C6—Fe1—C3—C4 | −171.0 (5) | C7—C8—C9—Fe1 | 59.8 (4) |
C1—Fe1—C3—C4 | −81.2 (4) | C3—Fe1—C9—C10 | −166.6 (4) |
C8—Fe1—C3—C4 | 118.8 (4) | C2—Fe1—C9—C10 | 159.5 (7) |
C9—Fe1—C3—C4 | 78.3 (4) | C7—Fe1—C9—C10 | 81.4 (5) |
C10—Fe1—C3—C4 | 51.2 (8) | C5—Fe1—C9—C10 | −82.5 (5) |
C7—Fe1—C3—C2 | −81.5 (4) | C6—Fe1—C9—C10 | 37.6 (4) |
C5—Fe1—C3—C2 | 82.0 (4) | C4—Fe1—C9—C10 | −124.8 (4) |
C6—Fe1—C3—C2 | −51.9 (7) | C1—Fe1—C9—C10 | −48.2 (12) |
C4—Fe1—C3—C2 | 119.1 (5) | C8—Fe1—C9—C10 | 119.1 (8) |
C1—Fe1—C3—C2 | 37.9 (3) | C3—Fe1—C9—C8 | 74.3 (7) |
C8—Fe1—C3—C2 | −122.1 (4) | C2—Fe1—C9—C8 | 40.3 (12) |
C9—Fe1—C3—C2 | −162.6 (3) | C7—Fe1—C9—C8 | −37.7 (6) |
C10—Fe1—C3—C2 | 170.3 (6) | C5—Fe1—C9—C8 | 158.3 (6) |
C2—C3—C4—C5 | −1.2 (7) | C6—Fe1—C9—C8 | −81.5 (6) |
Fe1—C3—C4—C5 | 58.5 (4) | C4—Fe1—C9—C8 | 116.0 (6) |
C2—C3—C4—Fe1 | −59.8 (4) | C1—Fe1—C9—C8 | −167.3 (9) |
C2—Fe1—C4—C3 | 38.0 (3) | C10—Fe1—C9—C8 | −119.1 (8) |
C7—Fe1—C4—C3 | −46.0 (7) | C7—C6—C10—C9 | −0.2 (7) |
C5—Fe1—C4—C3 | 120.3 (5) | Fe1—C6—C10—C9 | 59.6 (4) |
C6—Fe1—C4—C3 | 167.4 (7) | C7—C6—C10—Fe1 | −59.8 (4) |
C1—Fe1—C4—C3 | 82.3 (3) | C8—C9—C10—C6 | 0.0 (7) |
C8—Fe1—C4—C3 | −78.1 (4) | Fe1—C9—C10—C6 | −59.3 (4) |
C9—Fe1—C4—C3 | −120.6 (4) | C8—C9—C10—Fe1 | 59.3 (4) |
C10—Fe1—C4—C3 | −161.5 (3) | C3—Fe1—C10—C6 | 155.1 (7) |
C3—Fe1—C4—C5 | −120.3 (5) | C2—Fe1—C10—C6 | −42.0 (8) |
C2—Fe1—C4—C5 | −82.3 (4) | C7—Fe1—C10—C6 | 38.0 (4) |
C7—Fe1—C4—C5 | −166.3 (5) | C5—Fe1—C10—C6 | −123.9 (4) |
C6—Fe1—C4—C5 | 47.2 (10) | C4—Fe1—C10—C6 | −166.5 (4) |
C1—Fe1—C4—C5 | −38.0 (3) | C1—Fe1—C10—C6 | −80.4 (4) |
C8—Fe1—C4—C5 | 161.7 (3) | C8—Fe1—C10—C6 | 81.2 (5) |
C9—Fe1—C4—C5 | 119.1 (4) | C9—Fe1—C10—C6 | 118.9 (6) |
C10—Fe1—C4—C5 | 78.2 (4) | C3—Fe1—C10—C9 | 36.1 (9) |
C3—C4—C5—C1 | 1.4 (7) | C2—Fe1—C10—C9 | −160.9 (6) |
Fe1—C4—C5—C1 | 59.8 (4) | C7—Fe1—C10—C9 | −81.0 (5) |
C3—C4—C5—Fe1 | −58.4 (4) | C5—Fe1—C10—C9 | 117.2 (4) |
C2—C1—C5—C4 | −1.0 (6) | C6—Fe1—C10—C9 | −118.9 (6) |
C11—C1—C5—C4 | 175.4 (5) | C4—Fe1—C10—C9 | 74.6 (5) |
Fe1—C1—C5—C4 | −59.8 (4) | C1—Fe1—C10—C9 | 160.7 (4) |
C2—C1—C5—Fe1 | 58.8 (3) | C8—Fe1—C10—C9 | −37.7 (5) |
C11—C1—C5—Fe1 | −124.8 (6) | C5—C1—C11—O12 | 149.8 (5) |
C3—Fe1—C5—C4 | 36.9 (4) | C2—C1—C11—O12 | −34.5 (7) |
C2—Fe1—C5—C4 | 80.9 (4) | Fe1—C1—C11—O12 | 58.0 (6) |
C7—Fe1—C5—C4 | 160.2 (8) | C5—C1—C11—C16 | −93.7 (6) |
C6—Fe1—C5—C4 | −164.5 (4) | C2—C1—C11—C16 | 82.0 (7) |
C1—Fe1—C5—C4 | 119.0 (5) | Fe1—C1—C11—C16 | 174.5 (4) |
C8—Fe1—C5—C4 | −42.9 (8) | C5—C1—C11—C15 | 35.6 (7) |
C9—Fe1—C5—C4 | −79.7 (5) | C2—C1—C11—C15 | −148.7 (5) |
C10—Fe1—C5—C4 | −122.6 (4) | Fe1—C1—C11—C15 | −56.1 (6) |
C3—Fe1—C5—C1 | −82.1 (4) | C1—C11—O12—C13 | −133.0 (5) |
C2—Fe1—C5—C1 | −38.1 (4) | C16—C11—O12—C13 | 106.9 (5) |
C7—Fe1—C5—C1 | 41.2 (10) | C15—C11—O12—C13 | −11.9 (6) |
C6—Fe1—C5—C1 | 76.5 (4) | C11—O12—C13—O13 | 178.5 (6) |
C4—Fe1—C5—C1 | −119.0 (5) | C11—O12—C13—C14 | −1.4 (7) |
C8—Fe1—C5—C1 | −161.8 (7) | O13—C13—C14—C15 | −165.4 (7) |
C9—Fe1—C5—C1 | 161.3 (5) | O12—C13—C14—C15 | 14.5 (7) |
C10—Fe1—C5—C1 | 118.4 (4) | C13—C14—C15—C11 | −20.7 (6) |
C3—Fe1—C6—C7 | −41.5 (7) | C1—C11—C15—C14 | 135.8 (5) |
C2—Fe1—C6—C7 | −78.7 (4) | O12—C11—C15—C14 | 19.9 (5) |
C5—Fe1—C6—C7 | −164.7 (4) | C16—C11—C15—C14 | −94.9 (6) |
C4—Fe1—C6—C7 | 158.8 (8) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C8—H8···O13i | 0.93 | 2.47 | 3.290 (9) | 147 |
C14—H14A···Cg1ii | 0.97 | 2.89 | 3.777 (9) | 153 |
Symmetry codes: (i) −x+1, y+1/2, −z+2; (ii) −x+1, y−1/2, −z+1. |