Bis{2-[2-(4-nitro­phen­oxy)eth­oxy]eth­yl} ferrocene-1,1'-dicarboxyl­ate

The title compound, [Fe(C₁₆H₁₆NO₆)₂], has been synthesized by reacting 1,1'-bis­(chloro­carbon­yl)ferrocene with 2-[2-(4-nitro­phen­oxy)eth­oxy]ethanol. The metal ion is localized on a twofold axis and the whole mol­ecule is V-shaped, with an angle of 78.63 (2)° between the two cyclo­penta­dienyl arms (non-bonding angle between N atoms of nitro groups and Fe as pivot). The C-1-centroid-centroid-C-1' pseudo-torsion angle is 45.1 (8)°.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.031
• wR factor = 0.082
• Data-to-parameter ratio = 13.0

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT764_ALERT_4_C Overcomplete CIF Bond List Detected (Rep/Expd) .       1.18 Ratio

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   1 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 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
   1 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: SMART (Bruker, 1999); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1999); software used to prepare material for publication: SHELXTL.

1,1'-Bis{2-[2-(4-nitrophenoxy)ethoxy]ethyl}ferrocene dicarboxylate

Crystal data

[Fe(C16H16NO6)2]	F(000) = 1440
Mr = 692.45	Dx = 1.520 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 4888 reflections
a = 17.326 (3) Å	θ = 2.8–27.0°
b = 8.0669 (15) Å	µ = 0.57 mm^−1
c = 21.673 (4) Å	T = 298 K
β = 92.441 (2)°	Block, red
V = 3026.4 (10) Å^3	0.32 × 0.28 × 0.14 mm
Z = 4

Data collection

Bruker SMART CCD area-detector diffractometer	2775 independent reflections
Radiation source: fine-focus sealed tube	2537 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.020
φ and ω scans	θmax = 25.5°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 1999)	h = −13→20
Tmin = 0.839, Tmax = 0.925	k = −9→9
7611 measured reflections	l = −26→24

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.031	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.082	H-atom parameters constrained
S = 1.05	w = 1/[σ^2(Fo^2) + (0.0501P)^2 + 0.8069P] where P = (Fo^2 + 2Fc^2)/3
2775 reflections	(Δ/σ)max < 0.001
213 parameters	Δρmax = 0.38 e Å^−3
0 restraints	Δρmin = −0.22 e Å^−3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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 (Ų)

	x	y	z	Uiso*/Ueq
Fe1	0.0000	0.20534 (3)	0.2500	0.02922 (12)
C1	0.08622 (9)	0.3374 (2)	0.21249 (7)	0.0334 (3)
C2	0.11527 (10)	0.1828 (2)	0.23547 (8)	0.0384 (4)
H2	0.1544	0.1684	0.2657	0.046*
C3	0.07386 (11)	0.0554 (2)	0.20393 (8)	0.0427 (4)
H3	0.0810	−0.0578	0.2098	0.051*
C4	0.01928 (11)	0.1301 (2)	0.16163 (7)	0.0415 (4)
H4	−0.0153	0.0739	0.1352	0.050*
C5	0.02656 (10)	0.3038 (2)	0.16663 (7)	0.0371 (4)
H5	−0.0022	0.3822	0.1442	0.044*
C6	0.10763 (9)	0.5052 (2)	0.23286 (7)	0.0360 (4)
C7	0.17669 (11)	0.6632 (2)	0.30904 (9)	0.0459 (4)
H7A	0.1884	0.7385	0.2758	0.055*
H7B	0.2229	0.6515	0.3356	0.055*
C8	0.11333 (11)	0.7352 (2)	0.34558 (8)	0.0416 (4)
H8A	0.1277	0.8453	0.3599	0.050*
H8B	0.0663	0.7441	0.3198	0.050*
C9	0.04471 (11)	0.6910 (2)	0.43667 (8)	0.0442 (4)
H9A	0.0193	0.5980	0.4556	0.053*
H9B	0.0059	0.7522	0.4125	0.053*
C10	0.07844 (11)	0.8023 (2)	0.48676 (8)	0.0431 (4)
H10A	0.0436	0.8085	0.5206	0.052*
H10B	0.1274	0.7578	0.5026	0.052*
C11	0.12271 (9)	1.0825 (2)	0.49865 (7)	0.0365 (4)
C12	0.14761 (10)	1.0565 (2)	0.55979 (7)	0.0421 (4)
H12	0.1428	0.9523	0.5776	0.051*
C13	0.17951 (11)	1.1860 (2)	0.59388 (8)	0.0440 (4)
H13	0.1962	1.1700	0.6348	0.053*
C14	0.18638 (10)	1.3394 (2)	0.56646 (8)	0.0398 (4)
C15	0.16288 (10)	1.3672 (2)	0.50565 (8)	0.0407 (4)
H15	0.1682	1.4714	0.4880	0.049*
C16	0.13133 (10)	1.2376 (2)	0.47168 (8)	0.0402 (4)
H16	0.1157	1.2539	0.4305	0.048*
N1	0.22032 (9)	1.4756 (2)	0.60237 (7)	0.0495 (4)
O1	0.08467 (8)	0.63030 (15)	0.20762 (6)	0.0487 (3)
O2	0.15571 (7)	0.50293 (14)	0.28321 (5)	0.0421 (3)
O3	0.10075 (7)	0.63020 (15)	0.39685 (5)	0.0447 (3)
O4	0.08979 (7)	0.96479 (14)	0.46151 (5)	0.0439 (3)
O5	0.21893 (11)	1.6148 (2)	0.58011 (8)	0.0829 (5)
O6	0.25022 (9)	1.4463 (2)	0.65316 (6)	0.0664 (4)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Fe1	0.03731 (19)	0.02449 (18)	0.02585 (17)	0.000	0.00122 (12)	0.000
C1	0.0375 (8)	0.0329 (8)	0.0304 (7)	−0.0004 (7)	0.0080 (6)	−0.0013 (6)
C2	0.0376 (9)	0.0393 (9)	0.0385 (8)	0.0072 (7)	0.0046 (7)	−0.0005 (7)
C3	0.0556 (11)	0.0310 (8)	0.0425 (9)	0.0069 (8)	0.0117 (8)	−0.0046 (7)
C4	0.0565 (11)	0.0393 (9)	0.0290 (8)	−0.0040 (8)	0.0046 (7)	−0.0078 (7)
C5	0.0486 (10)	0.0372 (9)	0.0256 (7)	−0.0007 (7)	0.0037 (6)	0.0013 (6)
C6	0.0380 (8)	0.0359 (9)	0.0349 (8)	−0.0034 (7)	0.0087 (6)	−0.0013 (7)
C7	0.0449 (10)	0.0436 (10)	0.0493 (10)	−0.0103 (8)	0.0036 (8)	−0.0125 (8)
C8	0.0476 (10)	0.0355 (8)	0.0418 (9)	−0.0041 (7)	0.0026 (7)	−0.0042 (7)
C9	0.0457 (10)	0.0409 (10)	0.0463 (10)	−0.0039 (8)	0.0062 (8)	−0.0006 (7)
C10	0.0519 (11)	0.0396 (9)	0.0380 (9)	0.0032 (8)	0.0045 (8)	0.0004 (7)
C11	0.0359 (8)	0.0398 (9)	0.0340 (8)	0.0040 (7)	0.0046 (6)	−0.0049 (7)
C12	0.0475 (10)	0.0435 (10)	0.0357 (8)	−0.0005 (8)	0.0058 (7)	0.0034 (7)
C13	0.0461 (10)	0.0541 (11)	0.0318 (8)	−0.0006 (8)	0.0028 (7)	−0.0003 (7)
C14	0.0321 (8)	0.0437 (9)	0.0437 (9)	0.0019 (7)	0.0025 (7)	−0.0079 (7)
C15	0.0386 (9)	0.0378 (9)	0.0456 (9)	0.0056 (7)	0.0014 (7)	0.0007 (7)
C16	0.0441 (10)	0.0427 (9)	0.0335 (8)	0.0058 (8)	−0.0011 (7)	0.0000 (7)
N1	0.0433 (8)	0.0532 (10)	0.0516 (9)	−0.0024 (7)	−0.0028 (7)	−0.0083 (7)
O1	0.0631 (8)	0.0341 (6)	0.0486 (7)	−0.0033 (6)	0.0007 (6)	0.0054 (5)
O2	0.0458 (7)	0.0377 (6)	0.0425 (6)	−0.0017 (5)	0.0000 (5)	−0.0078 (5)
O3	0.0554 (7)	0.0378 (6)	0.0412 (6)	0.0059 (5)	0.0065 (5)	−0.0008 (5)
O4	0.0599 (8)	0.0353 (6)	0.0360 (6)	0.0010 (5)	−0.0041 (5)	−0.0015 (5)
O5	0.1087 (14)	0.0438 (9)	0.0924 (12)	−0.0036 (9)	−0.0418 (10)	−0.0052 (8)
O6	0.0710 (10)	0.0750 (10)	0.0518 (8)	−0.0184 (8)	−0.0152 (7)	−0.0048 (7)

Geometric parameters (Å, º)

Fe1—Fe1^i	0.0000 (6)	C7—O2	1.449 (2)
Fe1—C1	2.0327 (16)	C7—C8	1.498 (3)
Fe1—C1^i	2.0327 (16)	C7—H7A	0.9700
Fe1—C2^i	2.0431 (17)	C7—H7B	0.9700
Fe1—C2	2.0431 (17)	C8—O3	1.421 (2)
Fe1—C5^i	2.0440 (16)	C8—H8A	0.9700
Fe1—C5	2.0440 (16)	C8—H8B	0.9700
Fe1—C4^i	2.0501 (16)	C9—O3	1.414 (2)
Fe1—C4	2.0501 (16)	C9—C10	1.507 (2)
Fe1—C3^i	2.0508 (17)	C9—H9A	0.9700
Fe1—C3	2.0508 (17)	C9—H9B	0.9700
C1—C2	1.427 (2)	C10—O4	1.437 (2)
C1—C5	1.429 (2)	C10—H10A	0.9700
C1—C6	1.466 (2)	C10—H10B	0.9700
C1—Fe1^i	2.0327 (16)	C11—O4	1.3551 (19)
C2—C3	1.413 (2)	C11—C16	1.391 (2)
C2—Fe1^i	2.0431 (17)	C11—C12	1.392 (2)
C2—H2	0.9300	C12—C13	1.381 (2)
C3—C4	1.422 (3)	C12—H12	0.9300
C3—Fe1^i	2.0508 (17)	C13—C14	1.380 (3)
C3—H3	0.9300	C13—H13	0.9300
C4—C5	1.411 (2)	C14—C15	1.381 (2)
C4—Fe1^i	2.0501 (16)	C14—N1	1.456 (2)
C4—H4	0.9300	C15—C16	1.378 (3)
C5—Fe1^i	2.0440 (16)	C15—H15	0.9300
C5—H5	0.9300	C16—H16	0.9300
C6—O1	1.207 (2)	N1—O6	1.220 (2)
C6—O2	1.344 (2)	N1—O5	1.222 (2)
Fe1^i—Fe1—C1	0 (10)	C2—C3—Fe1	69.52 (9)
Fe1^i—Fe1—C1^i	0 (10)	C4—C3—Fe1	69.68 (10)
C1—Fe1—C1^i	116.76 (9)	C2—C3—H3	125.9
Fe1^i—Fe1—C2^i	0 (10)	C4—C3—H3	125.9
C1—Fe1—C2^i	148.01 (7)	Fe1^i—C3—H3	126.5
C1^i—Fe1—C2^i	40.99 (6)	Fe1—C3—H3	126.5
Fe1^i—Fe1—C2	0 (10)	C5—C4—C3	108.43 (15)
C1—Fe1—C2	40.99 (6)	C5—C4—Fe1^i	69.61 (9)
C1^i—Fe1—C2	148.01 (7)	C3—C4—Fe1^i	69.73 (9)
C2^i—Fe1—C2	169.79 (9)	C5—C4—Fe1	69.61 (9)
Fe1^i—Fe1—C5^i	0 (10)	C3—C4—Fe1	69.73 (9)
C1—Fe1—C5^i	110.29 (6)	C5—C4—H4	125.8
C1^i—Fe1—C5^i	41.04 (6)	C3—C4—H4	125.8
C2^i—Fe1—C5^i	68.90 (7)	Fe1^i—C4—H4	126.5
C2—Fe1—C5^i	115.42 (7)	Fe1—C4—H4	126.5
Fe1^i—Fe1—C5	0 (10)	C4—C5—C1	107.57 (14)
C1—Fe1—C5	41.04 (6)	C4—C5—Fe1^i	70.08 (9)
C1^i—Fe1—C5	110.29 (6)	C1—C5—Fe1^i	69.05 (9)
C2^i—Fe1—C5	115.42 (7)	C4—C5—Fe1	70.08 (9)
C2—Fe1—C5	68.90 (7)	C1—C5—Fe1	69.05 (9)
C5^i—Fe1—C5	134.27 (9)	C4—C5—H5	126.2
Fe1^i—Fe1—C4^i	0 (10)	C1—C5—H5	126.2
C1—Fe1—C4^i	132.90 (7)	Fe1^i—C5—H5	126.2
C1^i—Fe1—C4^i	68.27 (7)	Fe1—C5—H5	126.2
C2^i—Fe1—C4^i	68.31 (7)	O1—C6—O2	124.05 (15)
C2—Fe1—C4^i	108.48 (7)	O1—C6—C1	124.11 (15)
C5^i—Fe1—C4^i	40.31 (7)	O2—C6—C1	111.84 (14)
C5—Fe1—C4^i	173.06 (7)	O2—C7—C8	111.89 (14)
Fe1^i—Fe1—C4	0 (10)	O2—C7—H7A	109.2
C1—Fe1—C4	68.27 (7)	C8—C7—H7A	109.2
C1^i—Fe1—C4	132.90 (7)	O2—C7—H7B	109.2
C2^i—Fe1—C4	108.48 (7)	C8—C7—H7B	109.2
C2—Fe1—C4	68.31 (7)	H7A—C7—H7B	107.9
C5^i—Fe1—C4	173.06 (7)	O3—C8—C7	108.79 (15)
C5—Fe1—C4	40.31 (7)	O3—C8—H8A	109.9
C4^i—Fe1—C4	145.55 (10)	C7—C8—H8A	109.9
Fe1^i—Fe1—C3^i	0 (10)	O3—C8—H8B	109.9
C1—Fe1—C3^i	171.24 (7)	C7—C8—H8B	109.9
C1^i—Fe1—C3^i	68.28 (7)	H8A—C8—H8B	108.3
C2^i—Fe1—C3^i	40.37 (7)	O3—C9—C10	113.03 (15)
C2—Fe1—C3^i	131.06 (7)	O3—C9—H9A	109.0
C5^i—Fe1—C3^i	68.29 (7)	C10—C9—H9A	109.0
C5—Fe1—C3^i	145.91 (7)	O3—C9—H9B	109.0
C4^i—Fe1—C3^i	40.59 (7)	C10—C9—H9B	109.0
C4—Fe1—C3^i	114.21 (7)	H9A—C9—H9B	107.8
Fe1^i—Fe1—C3	0 (10)	O4—C10—C9	108.91 (14)
C1—Fe1—C3	68.28 (7)	O4—C10—H10A	109.9
C1^i—Fe1—C3	171.24 (7)	C9—C10—H10A	109.9
C2^i—Fe1—C3	131.06 (7)	O4—C10—H10B	109.9
C2—Fe1—C3	40.37 (7)	C9—C10—H10B	109.9
C5^i—Fe1—C3	145.91 (7)	H10A—C10—H10B	108.3
C5—Fe1—C3	68.29 (7)	O4—C11—C16	115.51 (14)
C4^i—Fe1—C3	114.21 (7)	O4—C11—C12	124.41 (15)
C4—Fe1—C3	40.59 (7)	C16—C11—C12	120.08 (15)
C3^i—Fe1—C3	107.73 (10)	C13—C12—C11	119.71 (17)
C2—C1—C5	108.09 (14)	C13—C12—H12	120.1
C2—C1—C6	128.37 (15)	C11—C12—H12	120.1
C5—C1—C6	123.44 (14)	C14—C13—C12	119.19 (16)
C2—C1—Fe1^i	69.90 (9)	C14—C13—H13	120.4
C5—C1—Fe1^i	69.91 (9)	C12—C13—H13	120.4
C6—C1—Fe1^i	122.97 (11)	C13—C14—C15	121.96 (16)
C2—C1—Fe1	69.90 (9)	C13—C14—N1	119.13 (16)
C5—C1—Fe1	69.91 (9)	C15—C14—N1	118.91 (17)
C6—C1—Fe1	122.97 (11)	C16—C15—C14	118.71 (17)
C3—C2—C1	107.62 (15)	C16—C15—H15	120.6
C3—C2—Fe1^i	70.10 (10)	C14—C15—H15	120.6
C1—C2—Fe1^i	69.11 (9)	C15—C16—C11	120.33 (16)
C3—C2—Fe1	70.10 (10)	C15—C16—H16	119.8
C1—C2—Fe1	69.11 (9)	C11—C16—H16	119.8
C3—C2—H2	126.2	O6—N1—O5	122.35 (17)
C1—C2—H2	126.2	O6—N1—C14	118.85 (17)
Fe1^i—C2—H2	126.2	O5—N1—C14	118.79 (15)
Fe1—C2—H2	126.2	C6—O2—C7	115.99 (13)
C2—C3—C4	108.30 (15)	C9—O3—C8	113.73 (13)
C2—C3—Fe1^i	69.52 (9)	C11—O4—C10	118.29 (13)
C4—C3—Fe1^i	69.68 (10)
Fe1^i—Fe1—C1—C2	0.000 (16)	C2—C3—C4—Fe1^i	−58.98 (12)
C1^i—Fe1—C1—C2	150.22 (10)	Fe1—C3—C4—Fe1^i	0.0
C2^i—Fe1—C1—C2	−171.83 (8)	C2—C3—C4—Fe1	−58.98 (12)
C5^i—Fe1—C1—C2	105.79 (10)	Fe1^i—C3—C4—Fe1	0.0
C5—Fe1—C1—C2	−119.08 (13)	Fe1^i—Fe1—C4—C5	0.00 (3)
C4^i—Fe1—C1—C2	65.81 (12)	C1—Fe1—C4—C5	−38.25 (10)
C4—Fe1—C1—C2	−81.49 (10)	C1^i—Fe1—C4—C5	68.69 (13)
C3—Fe1—C1—C2	−37.64 (10)	C2^i—Fe1—C4—C5	107.80 (11)
Fe1^i—Fe1—C1—C5	0.000 (19)	C2—Fe1—C4—C5	−82.53 (11)
C1^i—Fe1—C1—C5	−90.71 (9)	C4^i—Fe1—C4—C5	−173.85 (11)
C2^i—Fe1—C1—C5	−52.75 (16)	C3^i—Fe1—C4—C5	150.87 (10)
C2—Fe1—C1—C5	119.08 (13)	C3—Fe1—C4—C5	−119.79 (15)
C5^i—Fe1—C1—C5	−135.13 (10)	Fe1^i—Fe1—C4—C3	0.00 (3)
C4^i—Fe1—C1—C5	−175.12 (10)	C1—Fe1—C4—C3	81.54 (11)
C4—Fe1—C1—C5	37.59 (10)	C1^i—Fe1—C4—C3	−171.52 (10)
C3—Fe1—C1—C5	81.44 (10)	C2^i—Fe1—C4—C3	−132.41 (11)
Fe1^i—Fe1—C1—C6	0.000 (19)	C2—Fe1—C4—C3	37.26 (10)
C1^i—Fe1—C1—C6	26.81 (11)	C4^i—Fe1—C4—C3	−54.06 (9)
C2^i—Fe1—C1—C6	64.76 (19)	C3^i—Fe1—C4—C3	−89.34 (15)
C2—Fe1—C1—C6	−123.41 (17)	C1—Fe1—C4—Fe1^i	0 (9)
C5^i—Fe1—C1—C6	−17.61 (15)	C1^i—Fe1—C4—Fe1^i	0 (100)
C5—Fe1—C1—C6	117.52 (17)	C2^i—Fe1—C4—Fe1^i	0 (100)
C4^i—Fe1—C1—C6	−57.60 (17)	C2—Fe1—C4—Fe1^i	0 (36)
C4—Fe1—C1—C6	155.11 (15)	C3^i—Fe1—C4—Fe1^i	0 (100)
C3—Fe1—C1—C6	−161.04 (15)	C3—Fe1—C4—Fe1^i	0 (74)
C1^i—Fe1—C1—Fe1^i	0 (85)	C3—C4—C5—C1	−0.01 (19)
C2^i—Fe1—C1—Fe1^i	0 (100)	Fe1^i—C4—C5—C1	59.10 (11)
C2—Fe1—C1—Fe1^i	0 (75)	Fe1—C4—C5—C1	59.10 (11)
C5^i—Fe1—C1—Fe1^i	0 (26)	C3—C4—C5—Fe1^i	−59.11 (12)
C5—Fe1—C1—Fe1^i	0 (100)	Fe1—C4—C5—Fe1^i	0.0
C4^i—Fe1—C1—Fe1^i	0 (12)	C3—C4—C5—Fe1	−59.11 (12)
C4—Fe1—C1—Fe1^i	0 (100)	Fe1^i—C4—C5—Fe1	0.0
C5—C1—C2—C3	0.07 (18)	C2—C1—C5—C4	−0.04 (18)
C6—C1—C2—C3	176.49 (15)	C6—C1—C5—C4	−176.67 (14)
Fe1^i—C1—C2—C3	59.78 (12)	Fe1^i—C1—C5—C4	−59.74 (11)
Fe1—C1—C2—C3	59.78 (12)	Fe1—C1—C5—C4	−59.74 (11)
C5—C1—C2—Fe1^i	−59.71 (11)	C2—C1—C5—Fe1^i	59.70 (11)
C6—C1—C2—Fe1^i	116.71 (16)	C6—C1—C5—Fe1^i	−116.93 (15)
Fe1—C1—C2—Fe1^i	0.0	Fe1—C1—C5—Fe1^i	0.0
C5—C1—C2—Fe1	−59.71 (11)	C2—C1—C5—Fe1	59.70 (11)
C6—C1—C2—Fe1	116.71 (16)	C6—C1—C5—Fe1	−116.93 (15)
Fe1^i—C1—C2—Fe1	0.0	Fe1^i—C1—C5—Fe1	0.0
Fe1^i—Fe1—C2—C3	0.000 (8)	Fe1^i—Fe1—C5—C4	0.00 (3)
C1—Fe1—C2—C3	−118.86 (14)	C1—Fe1—C5—C4	118.85 (14)
C1^i—Fe1—C2—C3	−175.71 (11)	C1^i—Fe1—C5—C4	−133.31 (10)
C5^i—Fe1—C2—C3	148.93 (10)	C2^i—Fe1—C5—C4	−88.98 (12)
C5—Fe1—C2—C3	−80.90 (11)	C2—Fe1—C5—C4	80.94 (11)
C4^i—Fe1—C2—C3	105.93 (11)	C5^i—Fe1—C5—C4	−173.62 (11)
C4—Fe1—C2—C3	−37.46 (10)	C3^i—Fe1—C5—C4	−52.38 (17)
C3^i—Fe1—C2—C3	66.36 (16)	C3—Fe1—C5—C4	37.43 (11)
Fe1^i—Fe1—C2—C1	0.000 (7)	Fe1^i—Fe1—C5—C1	0.00 (3)
C1^i—Fe1—C2—C1	−56.85 (19)	C1^i—Fe1—C5—C1	107.84 (12)
C5^i—Fe1—C2—C1	−92.21 (10)	C2^i—Fe1—C5—C1	152.17 (9)
C5—Fe1—C2—C1	37.96 (9)	C2—Fe1—C5—C1	−37.91 (9)
C4^i—Fe1—C2—C1	−135.21 (9)	C5^i—Fe1—C5—C1	67.53 (8)
C4—Fe1—C2—C1	81.40 (10)	C4—Fe1—C5—C1	−118.85 (14)
C3^i—Fe1—C2—C1	−174.79 (9)	C3^i—Fe1—C5—C1	−171.22 (11)
C3—Fe1—C2—C1	118.86 (14)	C3—Fe1—C5—C1	−81.42 (11)
C1—Fe1—C2—Fe1^i	0 (39)	C1—Fe1—C5—Fe1^i	0 (8)
C1^i—Fe1—C2—Fe1^i	0 (15)	C1^i—Fe1—C5—Fe1^i	0 (97)
C2^i—Fe1—C2—Fe1^i	0 (100)	C2^i—Fe1—C5—Fe1^i	0 (100)
C5^i—Fe1—C2—Fe1^i	0 (49)	C2—Fe1—C5—Fe1^i	0 (44)
C5—Fe1—C2—Fe1^i	0 (76)	C5^i—Fe1—C5—Fe1^i	0 (76)
C4^i—Fe1—C2—Fe1^i	0 (90)	C3^i—Fe1—C5—Fe1^i	0 (100)
C4—Fe1—C2—Fe1^i	0 (100)	C3—Fe1—C5—Fe1^i	0 (88)
C3^i—Fe1—C2—Fe1^i	0 (100)	C2—C1—C6—O1	173.83 (17)
C3—Fe1—C2—Fe1^i	0 (100)	C5—C1—C6—O1	−10.3 (3)
C1—C2—C3—C4	−0.08 (19)	Fe1^i—C1—C6—O1	−96.68 (18)
Fe1^i—C2—C3—C4	59.08 (12)	Fe1—C1—C6—O1	−96.68 (18)
Fe1—C2—C3—C4	59.08 (12)	C2—C1—C6—O2	−6.4 (2)
C1—C2—C3—Fe1^i	−59.15 (11)	C5—C1—C6—O2	169.50 (14)
Fe1—C2—C3—Fe1^i	0.0	Fe1^i—C1—C6—O2	83.08 (16)
C1—C2—C3—Fe1	−59.15 (11)	Fe1—C1—C6—O2	83.08 (16)
Fe1^i—C2—C3—Fe1	0.0	O2—C7—C8—O3	63.34 (18)
Fe1^i—Fe1—C3—C2	0.00 (2)	O3—C9—C10—O4	79.99 (18)
C2^i—Fe1—C3—C2	−172.05 (7)	O4—C11—C12—C13	−179.10 (16)
C5^i—Fe1—C3—C2	−56.25 (16)	C16—C11—C12—C13	1.3 (3)
C5—Fe1—C3—C2	82.53 (11)	C11—C12—C13—C14	−0.2 (3)
C4^i—Fe1—C3—C2	−90.43 (11)	C12—C13—C14—C15	−0.6 (3)
C4—Fe1—C3—C2	119.71 (15)	C12—C13—C14—N1	−179.74 (16)
C3^i—Fe1—C3—C2	−133.52 (11)	C13—C14—C15—C16	0.3 (3)
Fe1^i—Fe1—C3—C4	0.00 (2)	N1—C14—C15—C16	179.50 (15)
C2^i—Fe1—C3—C4	68.24 (13)	C14—C15—C16—C11	0.7 (3)
C2—Fe1—C3—C4	−119.71 (15)	O4—C11—C16—C15	178.82 (15)
C5^i—Fe1—C3—C4	−175.96 (12)	C12—C11—C16—C15	−1.5 (3)
C5—Fe1—C3—C4	−37.18 (10)	C13—C14—N1—O6	8.7 (3)
C4^i—Fe1—C3—C4	149.86 (10)	C15—C14—N1—O6	−170.48 (17)
C3^i—Fe1—C3—C4	106.77 (11)	C13—C14—N1—O5	−172.46 (18)
C2^i—Fe1—C3—Fe1^i	0 (100)	C15—C14—N1—O5	8.3 (3)
C2—Fe1—C3—Fe1^i	0 (14)	O1—C6—O2—C7	3.2 (2)
C5^i—Fe1—C3—Fe1^i	0 (73)	C1—C6—O2—C7	−176.57 (13)
C5—Fe1—C3—Fe1^i	0 (71)	C8—C7—O2—C6	77.39 (19)
C4^i—Fe1—C3—Fe1^i	0 (100)	C10—C9—O3—C8	−88.84 (17)
C4—Fe1—C3—Fe1^i	0 (100)	C7—C8—O3—C9	176.76 (14)
C3^i—Fe1—C3—Fe1^i	0 (100)	C16—C11—O4—C10	−179.32 (15)
C2—C3—C4—C5	0.05 (19)	C12—C11—O4—C10	1.0 (2)
Fe1^i—C3—C4—C5	59.03 (11)	C9—C10—O4—C11	−177.39 (14)
Fe1—C3—C4—C5	59.03 (11)

Symmetry code: (i) −x, y, −z+1/2.