Methyl 3-ferrocenyl­propanoate

The title compound, [Fe(C₅H₅)(C₉H₁₁O₂)], was prepared and characterized by spectroscopic methods and crystal structure determination. The average values of the bond distances between the C atoms in the cyclo­penta­dienyl rings are 1.422 (3) Å in the substituted and 1.404 (4) Å in the unsubstituted ring. The Fe—C bond distances range from 2.036 (2) to 2.061 (2) Å and the bond angles in both rings range from 107.1 (2) to 108.9 (2)°. The cyclo­penta­dienyl rings are almost parallel and deviate only slightly from the eclipsed conformation. The mol­ecules are connected into dimers by very weak C—H...O intermolecular hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 295 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.036
• wR factor = 0.099
• Data-to-parameter ratio = 20.9

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


 Alert Level C:



PLAT_711  Alert C BOND    Unknown or Inconsistent Label ........       C
                           C      C(CP)(A

PLAT_711  Alert C BOND    Unknown or Inconsistent Label ........       C
                           C      C(CP)(A


 0 Alert Level A = Potentially serious problem

 0 Alert Level B = Potential problem

 2 Alert Level C = Please check

---

Computing details

Data collection: STADI4 (Stoe & Cie, 1995); cell refinement: STADI4; data reduction: X-RED (Stoe & Cie, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: WinGX (Farrugia, 1999); software used to prepare material for publication: SHELXL97.

Methyl 3-ferrocenylpropanoate

Crystal data

[Fe(C5H5)(C9H11O2)]	Dx = 1.464 Mg m^−3
Mr = 272.12	Melting point: 310-311 K K
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 29.425 (9) Å	Cell parameters from 28 reflections
b = 6.1454 (9) Å	θ = 6.2–13.3°
c = 13.739 (2) Å	µ = 1.21 mm^−1
β = 96.38 (1)°	T = 295 K
V = 2469.0 (9) Å^3	Prismatic, orange
Z = 8	0.90 × 0.75 × 0.60 mm
F(000) = 1136

Data collection

Philips PW1100 diffractometer updated by Stoe	2526 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.016
Graphite monochromator	θmax = 28.9°, θmin = 2.8°
ω scans	h = −40→39
Absorption correction: ψ scan (North et al., 1968)	k = 0→8
Tmin = 0.306, Tmax = 0.502	l = 0→18
3235 measured reflections	4 standard reflections every 120 min
3235 independent reflections	intensity decay: 2.4%

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.036	H-atom parameters constrained
wR(F^2) = 0.099	w = 1/[σ^2(Fo^2) + (0.0571P)^2 + 0.5699P] where P = (Fo^2 + 2Fc^2)/3
S = 1.07	(Δ/σ)max = 0.001
3235 reflections	Δρmax = 0.36 e Å^−3
155 parameters	Δρmin = −0.22 e Å^−3
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0027 (4)

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Fe	0.162609 (8)	0.23232 (4)	0.382015 (17)	0.03872 (11)
O1	0.00024 (5)	0.4304 (3)	0.12230 (13)	0.0702 (5)
O2	0.02558 (5)	0.7711 (2)	0.14370 (13)	0.0568 (4)
C1	0.13518 (7)	0.1983 (3)	0.23815 (13)	0.0442 (4)
C2	0.17506 (7)	0.3304 (4)	0.24491 (14)	0.0508 (4)
H2	0.1765	0.4733	0.2232	0.061*
C3	0.21260 (7)	0.2056 (4)	0.29097 (17)	0.0586 (5)
H3	0.2427	0.2531	0.3043	0.070*
C4	0.19594 (8)	−0.0021 (4)	0.31245 (16)	0.0579 (5)
H4	0.2130	−0.1157	0.3425	0.069*
C5	0.14835 (8)	−0.0068 (3)	0.28002 (15)	0.0538 (5)
H5	0.1290	−0.1248	0.2853	0.065*
C6	0.11346 (8)	0.3602 (5)	0.45857 (14)	0.0612 (6)
H6	0.0838	0.3948	0.4329	0.073*
C7	0.15144 (9)	0.4999 (4)	0.46429 (16)	0.0633 (6)
H7	0.1514	0.6437	0.4432	0.076*
C8	0.18986 (8)	0.3822 (5)	0.50805 (15)	0.0656 (6)
H8	0.2196	0.4348	0.5206	0.079*
C9	0.17499 (9)	0.1724 (5)	0.52890 (15)	0.0648 (6)
H9	0.1932	0.0613	0.5580	0.078*
C10	0.12835 (8)	0.1588 (5)	0.49862 (15)	0.0648 (6)
H10	0.1101	0.0368	0.5040	0.078*
C11	0.08782 (7)	0.2551 (3)	0.19239 (17)	0.0513 (5)
H11A	0.0657	0.1809	0.2279	0.062*
H11B	0.0840	0.2021	0.1255	0.062*
C12	0.07790 (6)	0.4962 (3)	0.19192 (14)	0.0456 (4)
H12A	0.0825	0.5496	0.2587	0.055*
H12B	0.0997	0.5698	0.1552	0.055*
C13	0.03046 (6)	0.5547 (3)	0.14850 (12)	0.0439 (4)
C14	−0.01873 (7)	0.8526 (4)	0.10525 (17)	0.0616 (5)
H14A	−0.0181	1.0088	0.1047	0.092*
H14B	−0.0413	0.8035	0.1457	0.092*
H14C	−0.0263	0.7998	0.0397	0.092*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Fe	0.03949 (16)	0.04113 (16)	0.03594 (15)	−0.00205 (10)	0.00601 (10)	−0.00138 (9)
O1	0.0583 (9)	0.0492 (8)	0.0977 (13)	−0.0082 (7)	−0.0158 (8)	0.0034 (8)
O2	0.0563 (8)	0.0422 (7)	0.0708 (10)	0.0002 (6)	0.0029 (7)	0.0001 (6)
C1	0.0497 (10)	0.0455 (9)	0.0372 (8)	0.0004 (8)	0.0037 (7)	−0.0084 (7)
C2	0.0519 (11)	0.0588 (11)	0.0433 (9)	−0.0047 (9)	0.0125 (8)	0.0037 (9)
C3	0.0446 (10)	0.0807 (15)	0.0523 (11)	0.0036 (10)	0.0125 (8)	0.0017 (10)
C4	0.0581 (12)	0.0603 (12)	0.0553 (11)	0.0167 (10)	0.0069 (10)	−0.0061 (9)
C5	0.0629 (12)	0.0419 (10)	0.0559 (11)	0.0018 (8)	0.0040 (9)	−0.0109 (8)
C6	0.0545 (11)	0.0905 (17)	0.0397 (9)	0.0186 (12)	0.0102 (8)	−0.0035 (11)
C7	0.0923 (17)	0.0497 (11)	0.0496 (11)	0.0059 (11)	0.0151 (11)	−0.0105 (9)
C8	0.0615 (13)	0.0838 (17)	0.0497 (11)	−0.0095 (12)	−0.0017 (10)	−0.0186 (11)
C9	0.0776 (15)	0.0749 (15)	0.0410 (10)	0.0176 (13)	0.0027 (10)	0.0057 (10)
C10	0.0729 (15)	0.0760 (15)	0.0489 (11)	−0.0108 (13)	0.0219 (10)	0.0058 (11)
C11	0.0534 (11)	0.0455 (10)	0.0519 (10)	−0.0009 (8)	−0.0080 (9)	−0.0098 (8)
C12	0.0486 (10)	0.0438 (9)	0.0444 (9)	−0.0050 (7)	0.0052 (8)	−0.0012 (7)
C13	0.0511 (10)	0.0428 (9)	0.0383 (8)	−0.0031 (8)	0.0071 (7)	0.0004 (7)
C14	0.0637 (13)	0.0537 (12)	0.0679 (13)	0.0091 (10)	0.0091 (10)	0.0101 (10)

Geometric parameters (Å, º)

C—C(Cp)(av.)subst.	1.421 (3)	C4—C5	1.422 (3)
C—C(Cp)(av.)unsubst.	1.404 (4)	C4—H4	0.9300
Fe—C10	2.036 (2)	C5—H5	0.9300
Fe—C6	2.038 (2)	C6—C10	1.404 (4)
Fe—C4	2.039 (2)	C6—C7	1.405 (4)
Fe—C3	2.041 (2)	C6—H6	0.9300
Fe—C5	2.0417 (19)	C7—C8	1.418 (3)
Fe—C7	2.043 (2)	C7—H7	0.9300
Fe—C9	2.044 (2)	C8—C9	1.401 (4)
Fe—C8	2.045 (2)	C8—H8	0.9300
Fe—C2	2.0492 (19)	C9—C10	1.392 (3)
Fe—C1	2.0609 (18)	C9—H9	0.9300
O1—C13	1.197 (2)	C10—H10	0.9300
O2—C13	1.338 (2)	C11—C12	1.510 (3)
O2—C14	1.441 (2)	C11—H11A	0.9700
C1—C2	1.422 (3)	C11—H11B	0.9700
C1—C5	1.421 (3)	C12—C13	1.500 (3)
C1—C11	1.505 (3)	C12—H12A	0.9700
C2—C3	1.433 (3)	C12—H12B	0.9700
C2—H2	0.9300	C14—H14A	0.9600
C3—C4	1.410 (3)	C14—H14B	0.9600
C3—H3	0.9300	C14—H14C	0.9600
C10—Fe—C6	40.33 (11)	C3—C4—C5	107.83 (19)
C10—Fe—C4	121.20 (11)	C3—C4—Fe	69.84 (12)
C6—Fe—C4	156.93 (11)	C5—C4—Fe	69.71 (11)
C10—Fe—C3	156.64 (11)	C3—C4—H4	126.1
C6—Fe—C3	161.56 (10)	C5—C4—H4	126.1
C4—Fe—C3	40.43 (10)	Fe—C4—H4	125.9
C10—Fe—C5	107.36 (10)	C1—C5—C4	108.87 (19)
C6—Fe—C5	121.88 (10)	C1—C5—Fe	70.46 (11)
C4—Fe—C5	40.78 (8)	C4—C5—Fe	69.52 (11)
C3—Fe—C5	68.19 (10)	C1—C5—H5	125.6
C10—Fe—C7	67.61 (11)	C4—C5—H5	125.6
C6—Fe—C7	40.27 (10)	Fe—C5—H5	126.0
C4—Fe—C7	160.62 (10)	C10—C6—C7	107.8 (2)
C3—Fe—C7	125.12 (10)	C10—C6—Fe	69.76 (12)
C5—Fe—C7	157.79 (10)	C7—C6—Fe	70.04 (12)
C10—Fe—C9	39.88 (9)	C10—C6—H6	126.1
C6—Fe—C9	67.59 (9)	C7—C6—H6	126.1
C4—Fe—C9	107.05 (10)	Fe—C6—H6	125.7
C3—Fe—C9	121.95 (10)	C6—C7—C8	107.7 (2)
C5—Fe—C9	123.27 (10)	C6—C7—Fe	69.69 (12)
C7—Fe—C9	67.70 (10)	C8—C7—Fe	69.78 (12)
C10—Fe—C8	67.38 (10)	C6—C7—H7	126.2
C6—Fe—C8	67.87 (10)	C8—C7—H7	126.2
C4—Fe—C8	123.46 (10)	Fe—C7—H7	125.9
C3—Fe—C8	108.29 (10)	C9—C8—C7	107.7 (2)
C5—Fe—C8	159.52 (10)	C9—C8—Fe	69.92 (12)
C7—Fe—C8	40.60 (10)	C7—C8—Fe	69.62 (11)
C9—Fe—C8	40.08 (11)	C9—C8—H8	126.2
C10—Fe—C2	160.61 (9)	C7—C8—H8	126.2
C6—Fe—C2	124.80 (9)	Fe—C8—H8	125.9
C4—Fe—C2	68.44 (9)	C10—C9—C8	108.3 (2)
C3—Fe—C2	41.02 (9)	C10—C9—Fe	69.76 (12)
C5—Fe—C2	67.97 (9)	C8—C9—Fe	69.99 (12)
C7—Fe—C2	109.15 (9)	C10—C9—H9	125.8
C9—Fe—C2	158.45 (10)	C8—C9—H9	125.8
C8—Fe—C2	123.54 (10)	Fe—C9—H9	126.0
C10—Fe—C1	123.83 (9)	C9—C10—C6	108.6 (2)
C6—Fe—C1	108.02 (8)	C9—C10—Fe	70.36 (13)
C4—Fe—C1	68.68 (8)	C6—C10—Fe	69.91 (11)
C3—Fe—C1	68.66 (9)	C9—C10—H10	125.7
C5—Fe—C1	40.54 (8)	C6—C10—H10	125.7
C7—Fe—C1	122.85 (9)	Fe—C10—H10	125.6
C9—Fe—C1	159.48 (11)	C1—C11—C12	113.53 (16)
C8—Fe—C1	158.87 (10)	C1—C11—H11A	108.9
C2—Fe—C1	40.47 (8)	C12—C11—H11A	108.9
C13—O2—C14	116.83 (17)	C1—C11—H11B	108.9
C2—C1—C5	107.09 (18)	C12—C11—H11B	108.9
C2—C1—C11	127.90 (19)	H11A—C11—H11B	107.7
C5—C1—C11	124.97 (18)	C13—C12—C11	114.07 (16)
C2—C1—Fe	69.32 (10)	C13—C12—H12A	108.7
C5—C1—Fe	69.00 (11)	C11—C12—H12A	108.7
C11—C1—Fe	128.53 (14)	C13—C12—H12B	108.7
C1—C2—C3	108.3 (2)	C11—C12—H12B	108.7
C1—C2—Fe	70.21 (11)	H12A—C12—H12B	107.6
C3—C2—Fe	69.17 (12)	O1—C13—O2	123.16 (19)
C1—C2—H2	125.9	O1—C13—C12	126.48 (18)
C3—C2—H2	125.9	O2—C13—C12	110.35 (16)
Fe—C2—H2	126.3	O2—C14—H14A	109.5
C4—C3—C2	107.94 (19)	O2—C14—H14B	109.5
C4—C3—Fe	69.73 (12)	H14A—C14—H14B	109.5
C2—C3—Fe	69.81 (11)	O2—C14—H14C	109.5
C4—C3—H3	126.0	H14A—C14—H14C	109.5
C2—C3—H3	126.0	H14B—C14—H14C	109.5
Fe—C3—H3	126.0
C10—Fe—C1—C2	164.58 (14)	C2—Fe—C5—C4	82.08 (14)
C6—Fe—C1—C2	122.92 (14)	C1—Fe—C5—C4	119.94 (18)
C4—Fe—C1—C2	−81.36 (14)	C4—Fe—C6—C10	43.7 (3)
C3—Fe—C1—C2	−37.81 (13)	C3—Fe—C6—C10	−162.1 (3)
C5—Fe—C1—C2	−118.77 (18)	C5—Fe—C6—C10	79.06 (16)
C7—Fe—C1—C2	81.07 (16)	C7—Fe—C6—C10	−118.7 (2)
C9—Fe—C1—C2	−163.0 (2)	C9—Fe—C6—C10	−37.18 (15)
C8—Fe—C1—C2	47.8 (3)	C8—Fe—C6—C10	−80.65 (16)
C10—Fe—C1—C5	−76.65 (16)	C2—Fe—C6—C10	163.00 (14)
C6—Fe—C1—C5	−118.31 (14)	C1—Fe—C6—C10	121.43 (14)
C4—Fe—C1—C5	37.41 (13)	C10—Fe—C6—C7	118.7 (2)
C3—Fe—C1—C5	80.97 (14)	C4—Fe—C6—C7	162.3 (2)
C7—Fe—C1—C5	−160.15 (14)	C3—Fe—C6—C7	−43.4 (3)
C9—Fe—C1—C5	−44.3 (3)	C5—Fe—C6—C7	−162.27 (13)
C8—Fe—C1—C5	166.6 (2)	C9—Fe—C6—C7	81.49 (16)
C2—Fe—C1—C5	118.77 (18)	C8—Fe—C6—C7	38.01 (14)
C10—Fe—C1—C11	42.0 (2)	C2—Fe—C6—C7	−78.33 (16)
C6—Fe—C1—C11	0.3 (2)	C1—Fe—C6—C7	−119.90 (14)
C4—Fe—C1—C11	156.0 (2)	C10—C6—C7—C8	0.1 (2)
C3—Fe—C1—C11	−160.4 (2)	Fe—C6—C7—C8	−59.68 (15)
C5—Fe—C1—C11	118.6 (2)	C10—C6—C7—Fe	59.82 (15)
C7—Fe—C1—C11	−41.5 (2)	C10—Fe—C7—C6	−37.89 (14)
C9—Fe—C1—C11	74.4 (3)	C4—Fe—C7—C6	−159.0 (2)
C8—Fe—C1—C11	−74.8 (3)	C3—Fe—C7—C6	164.58 (13)
C2—Fe—C1—C11	−122.6 (2)	C5—Fe—C7—C6	43.2 (3)
C5—C1—C2—C3	0.0 (2)	C9—Fe—C7—C6	−81.17 (15)
C11—C1—C2—C3	−177.75 (19)	C8—Fe—C7—C6	−118.8 (2)
Fe—C1—C2—C3	58.89 (14)	C2—Fe—C7—C6	121.65 (14)
C5—C1—C2—Fe	−58.89 (13)	C1—Fe—C7—C6	78.90 (15)
C11—C1—C2—Fe	123.4 (2)	C10—Fe—C7—C8	80.89 (16)
C10—Fe—C2—C1	−41.7 (4)	C6—Fe—C7—C8	118.8 (2)
C6—Fe—C2—C1	−76.45 (16)	C4—Fe—C7—C8	−40.2 (3)
C4—Fe—C2—C1	81.99 (14)	C3—Fe—C7—C8	−76.65 (17)
C3—Fe—C2—C1	119.55 (19)	C5—Fe—C7—C8	162.0 (2)
C5—Fe—C2—C1	37.92 (12)	C9—Fe—C7—C8	37.61 (15)
C7—Fe—C2—C1	−118.53 (14)	C2—Fe—C7—C8	−119.58 (15)
C9—Fe—C2—C1	163.8 (3)	C1—Fe—C7—C8	−162.32 (14)
C8—Fe—C2—C1	−161.31 (13)	C6—C7—C8—C9	−0.2 (2)
C10—Fe—C2—C3	−161.3 (3)	Fe—C7—C8—C9	−59.81 (15)
C6—Fe—C2—C3	164.00 (14)	C6—C7—C8—Fe	59.62 (15)
C4—Fe—C2—C3	−37.56 (14)	C10—Fe—C8—C9	37.25 (15)
C5—Fe—C2—C3	−81.63 (15)	C6—Fe—C8—C9	81.02 (16)
C7—Fe—C2—C3	121.92 (15)	C4—Fe—C8—C9	−76.15 (17)
C9—Fe—C2—C3	44.3 (3)	C3—Fe—C8—C9	−118.21 (15)
C8—Fe—C2—C3	79.14 (17)	C5—Fe—C8—C9	−41.7 (3)
C1—Fe—C2—C3	−119.55 (19)	C7—Fe—C8—C9	118.7 (2)
C1—C2—C3—C4	0.0 (2)	C2—Fe—C8—C9	−160.97 (14)
Fe—C2—C3—C4	59.53 (15)	C1—Fe—C8—C9	163.8 (2)
C1—C2—C3—Fe	−59.54 (14)	C10—Fe—C8—C7	−81.48 (16)
C10—Fe—C3—C4	45.3 (3)	C6—Fe—C8—C7	−37.71 (15)
C6—Fe—C3—C4	−164.8 (2)	C4—Fe—C8—C7	165.11 (14)
C5—Fe—C3—C4	−38.01 (13)	C3—Fe—C8—C7	123.05 (15)
C7—Fe—C3—C4	162.32 (13)	C5—Fe—C8—C7	−160.5 (3)
C9—Fe—C3—C4	78.53 (17)	C9—Fe—C8—C7	−118.7 (2)
C8—Fe—C3—C4	120.49 (15)	C2—Fe—C8—C7	80.30 (16)
C2—Fe—C3—C4	−119.06 (19)	C1—Fe—C8—C7	45.1 (3)
C1—Fe—C3—C4	−81.75 (14)	C7—C8—C9—C10	0.2 (2)
C10—Fe—C3—C2	164.4 (2)	Fe—C8—C9—C10	−59.45 (16)
C6—Fe—C3—C2	−45.7 (3)	C7—C8—C9—Fe	59.62 (15)
C4—Fe—C3—C2	119.06 (19)	C6—Fe—C9—C10	37.58 (18)
C5—Fe—C3—C2	81.05 (14)	C4—Fe—C9—C10	−118.54 (17)
C7—Fe—C3—C2	−78.62 (16)	C3—Fe—C9—C10	−160.21 (17)
C9—Fe—C3—C2	−162.41 (14)	C5—Fe—C9—C10	−76.79 (19)
C8—Fe—C3—C2	−120.45 (14)	C7—Fe—C9—C10	81.29 (18)
C1—Fe—C3—C2	37.31 (13)	C8—Fe—C9—C10	119.4 (2)
C2—C3—C4—C5	0.0 (2)	C2—Fe—C9—C10	167.1 (2)
Fe—C3—C4—C5	59.59 (14)	C1—Fe—C9—C10	−43.9 (3)
C2—C3—C4—Fe	−59.58 (15)	C10—Fe—C9—C8	−119.4 (2)
C10—Fe—C4—C3	−160.75 (14)	C6—Fe—C9—C8	−81.79 (17)
C6—Fe—C4—C3	167.75 (19)	C4—Fe—C9—C8	122.08 (15)
C5—Fe—C4—C3	118.92 (19)	C3—Fe—C9—C8	80.41 (18)
C7—Fe—C4—C3	−48.5 (3)	C5—Fe—C9—C8	163.83 (14)
C9—Fe—C4—C3	−119.56 (15)	C7—Fe—C9—C8	−38.08 (15)
C8—Fe—C4—C3	−78.72 (17)	C2—Fe—C9—C8	47.7 (3)
C2—Fe—C4—C3	38.09 (13)	C1—Fe—C9—C8	−163.3 (2)
C1—Fe—C4—C3	81.71 (14)	C8—C9—C10—C6	−0.1 (3)
C10—Fe—C4—C5	80.33 (15)	Fe—C9—C10—C6	−59.68 (15)
C6—Fe—C4—C5	48.8 (3)	C8—C9—C10—Fe	59.60 (15)
C3—Fe—C4—C5	−118.92 (19)	C7—C6—C10—C9	0.0 (2)
C7—Fe—C4—C5	−167.4 (2)	Fe—C6—C10—C9	59.96 (16)
C9—Fe—C4—C5	121.52 (14)	C7—C6—C10—Fe	−59.99 (14)
C8—Fe—C4—C5	162.36 (14)	C6—Fe—C10—C9	−119.4 (2)
C2—Fe—C4—C5	−80.83 (13)	C4—Fe—C10—C9	79.05 (19)
C1—Fe—C4—C5	−37.20 (12)	C3—Fe—C10—C9	46.4 (3)
C2—C1—C5—C4	0.0 (2)	C5—Fe—C10—C9	121.47 (16)
C11—C1—C5—C4	177.84 (18)	C7—Fe—C10—C9	−81.55 (18)
Fe—C1—C5—C4	−59.08 (14)	C8—Fe—C10—C9	−37.43 (17)
C2—C1—C5—Fe	59.09 (13)	C2—Fe—C10—C9	−165.7 (3)
C11—C1—C5—Fe	−123.08 (19)	C1—Fe—C10—C9	162.97 (16)
C3—C4—C5—C1	0.0 (2)	C4—Fe—C10—C6	−161.55 (14)
Fe—C4—C5—C1	59.66 (13)	C3—Fe—C10—C6	165.8 (2)
C3—C4—C5—Fe	−59.67 (15)	C5—Fe—C10—C6	−119.13 (15)
C10—Fe—C5—C1	122.13 (13)	C7—Fe—C10—C6	37.84 (15)
C6—Fe—C5—C1	80.40 (15)	C9—Fe—C10—C6	119.4 (2)
C4—Fe—C5—C1	−119.94 (18)	C8—Fe—C10—C6	81.96 (17)
C3—Fe—C5—C1	−82.24 (14)	C2—Fe—C10—C6	−46.3 (4)
C7—Fe—C5—C1	49.0 (3)	C1—Fe—C10—C6	−77.63 (18)
C9—Fe—C5—C1	162.98 (13)	C2—C1—C11—C12	−26.5 (3)
C8—Fe—C5—C1	−166.2 (2)	C5—C1—C11—C12	156.11 (19)
C2—Fe—C5—C1	−37.86 (12)	Fe—C1—C11—C12	66.2 (3)
C10—Fe—C5—C4	−117.93 (14)	C1—C11—C12—C13	−178.73 (16)
C6—Fe—C5—C4	−159.67 (14)	C14—O2—C13—O1	0.4 (3)
C3—Fe—C5—C4	37.70 (13)	C14—O2—C13—C12	−178.75 (16)
C7—Fe—C5—C4	168.9 (2)	C11—C12—C13—O1	5.8 (3)
C9—Fe—C5—C4	−77.08 (16)	C11—C12—C13—O2	−175.11 (18)
C8—Fe—C5—C4	−46.3 (3)