1-[(Z)-3-Ferrocenyl-1-(4-fluoro­phen­yl)-1-methoxy­prop-2-en-2-yl]-1H-1,2,4-triazole

The title compound, [Fe(C₅H₅)(C₁₇H₁₅FN₃O)], was synthesized unexpectedly during a search for potent fungicidal and plant growth regulatory agents. In the crystal structure, the mol­ecules form centrosymmetric dimers via weak inter­molecular C—H...F inter­actions. The planes of the substituted cyclo­penta­dienyl and benzene rings make dihedral angles of 93.9 (3) and 15.1 (2)°, respectively, with the triazole ring.

Key indicators

• Single-crystal X-ray study
• T = 294 K
• Mean [sigma](C-C) = 0.006 Å
• R factor = 0.042
• wR factor = 0.099
• Data-to-parameter ratio = 13.5

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.62 Ratio
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C6     -   C10     ..       6.47 su
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         C7
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         C8
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         C9
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C10
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        Fe1

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   7 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
   7 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
   0 ALERT type 4 Improvement, methodology, query or suggestion

---

S1. Comment

Ferrocene is stable, nontoxic, and can cross cell membranes (Dombrowsk et al., 1986; Yeay, 1969), and its derivatives offer exciting possibilities in insecticide and drug development (Motohashi et al., 1990; Biot et al., 2000), There are many studies reporting that higher activity can be achieved by introducing the ferrocenyl group into biologically active compounds (Huang & Wang, 2001; Molina et al., 1999; Fang et al., 2003). However, the concept of introducing ferrocenyl into triazole derivatives, which possess fungicidal, insecticidal, herbicidal and plant growth regulatory activites (Czollner et al., 1990; Chu et al., 1999), has not received much attention. In order to investigate novel biological triazole molecules containing the ferrocenyl moiety, we designed and synthesized some 1-aryl-3-ferrocenyl-2-(1H-1,2,4-triazole-1-yl)prop-2-en-1-ol derivatives. In this study, the crystal structure of an unexpected product, the title compound, (I), was determined.

The molecular structure of (I) is shown in Fig. 1. The molecule contains four essentially planar ring systems, viz. two cyclopentadienyl rings [p1 (C1–C5) and p2 (C6–C10)], a triazole ring (p3) and a substituted benzene ring (p4). The dihedral angles between p3 and p1, and between p3 and p4, are 93.9 (3) and 15.1 (2)°, respectively. The Fe—C distances in the ferrocenyl ring are normal and the distance of the cyclopentadienyl ring centroids Cg1 (C1–C5) and Cg2 (C6–C10) from atom Fe1 are not significantly different [1.638 (2) and 1.650 (3) Å, respectively]. The cyclopentadienyl rings are slightly staggered, as evidenced by the C1···Cg1···Cg2···C6 and C3···Cg1···Cg2···C8 pseudo-torsion angles of −12.0 (2) and −14.0 (3)°, respectively.

In the crystal structure of (I), weak intermolecular C—H···F interactions [H···Fⁱ = 2.511 Å, C···Fⁱ = 3.386 (3) Å and C11—H11···Fⁱ = 156.8(2°; symmetry code: (i) 1 − x, 1 − y, 2 − z] link the molecules into centrosymmetric dimers (Fig.2).

S2. Experimental

1-(4-Fluorophenyl)-3-ferrocenyl-2-(1H-1,2,4-triazol-1-yl)prop-2-en-1-one (4.2 g, 10 mmol) was dissolved in methanol (15 ml) and water (20 ml). Sodium borohydride (0.076 g, 20 mmol) was then added in six batches below 283 K. The mixture was stirred for 24 h at room temperature, then adjusted to pH 6 using 10% (w/w) sulfuric acid. The solution was extracted with diethyl ether (3 × 20 ml), and the combined organic layer was washed with water (3 × 20 ml) and then dried over anhydrous magnesium sulfate. After removal of the solvent, the residue was recrystallized from petroleum ether–ethyl acetate (4:1 v/v) to give yellow crystals of (I) (yield 56%).

S3. Refinement

All H atoms were placed in calculated positions, with C—H = 0.93 Å, or 0.96 Å for methyl H, and included in the refinement using a riding-model approximation, with U_iso(H) = 1.2U_eq(C), or 1.5U_eq(C) for methyl H.

Computing details

Data collection: SMART (Bruker, 1998); 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.

Figures

	Fig. 1. A view of (I), with displacement ellipsoids drawn at the 30% probability level.
	Fig. 2. A view (Spek, 2003) of a centrosymmtric dimer of (I). Dashed lines indicate weak C—H···F interactions.

1-[(Z)-3-Ferrocenyl-1-(4-fluorophenyl)-1-methoxyprop-2-en-2-yl]- 1H-1,2,4-triazole

Crystal data

[Fe(C5H5)(C17H15FN3O)]	Z = 2
Mr = 417.26	F(000) = 432
Triclinic, P1	Dx = 1.421 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.116 (2) Å	Cell parameters from 1579 reflections
b = 11.045 (3) Å	θ = 2.2–22.8°
c = 11.239 (3) Å	µ = 0.80 mm^−1
α = 100.554 (4)°	T = 294 K
β = 110.267 (4)°	Block, yellow
γ = 115.736 (4)°	0.24 × 0.22 × 0.18 mm
V = 975.0 (4) Å^3

Data collection

Bruker SMART CCD area-detector diffractometer	3417 independent reflections
Radiation source: fine-focus sealed tube	2445 reflections with I > 2/s(I)
Graphite monochromator	Rint = 0.025
ϕ and ω scans	θmax = 25.0°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −12→10
Tmin = 0.821, Tmax = 0.866	k = −7→13
4998 measured reflections	l = −12→13

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.099	H-atom parameters constrained
S = 1.02	w = 1/[σ^2(Fo^2) + (0.0447P)^2] where P = (Fo^2 + 2Fc^2)/3
3417 reflections	(Δ/σ)max = 0.004
254 parameters	Δρmax = 0.25 e Å^−3
0 restraints	Δρmin = −0.24 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
Fe1	0.64582 (5)	0.87958 (5)	0.67424 (4)	0.04078 (16)
F1	0.4790 (3)	0.4859 (3)	1.1747 (2)	0.0900 (7)
N1	0.1620 (3)	0.7821 (3)	0.6360 (2)	0.0384 (6)
N2	0.2250 (3)	0.9276 (3)	0.6931 (3)	0.0575 (7)
N3	−0.0015 (3)	0.8207 (3)	0.4837 (3)	0.0599 (8)
O1	−0.0115 (2)	0.5727 (2)	0.7255 (2)	0.0564 (6)
C1	0.4058 (3)	0.7134 (3)	0.5984 (3)	0.0355 (7)
C2	0.4123 (3)	0.8088 (3)	0.5271 (3)	0.0407 (7)
H2	0.3588	0.8596	0.5222	0.049*
C3	0.5128 (4)	0.8129 (3)	0.4655 (3)	0.0476 (8)
H3	0.5377	0.8675	0.4137	0.057*
C4	0.5695 (4)	0.7208 (3)	0.4956 (3)	0.0498 (8)
H4	0.6377	0.7035	0.4667	0.060*
C5	0.5050 (4)	0.6591 (3)	0.5771 (3)	0.0429 (7)
H5	0.5236	0.5942	0.6113	0.051*
C6	0.7288 (5)	0.9988 (5)	0.8728 (4)	0.0804 (13)
H6	0.6631	0.9876	0.9158	0.096*
C7	0.7611 (6)	1.0910 (4)	0.8010 (5)	0.0871 (13)
H7	0.7210	1.1515	0.7870	0.105*
C8	0.8670 (6)	1.0726 (5)	0.7546 (4)	0.0930 (16)
H8	0.9101	1.1195	0.7040	0.112*
C9	0.8950 (5)	0.9736 (6)	0.7972 (5)	0.0931 (15)
H9	0.9607	0.9419	0.7806	0.112*
C10	0.8107 (6)	0.9292 (5)	0.8681 (4)	0.0900 (14)
H10	0.8093	0.8617	0.9073	0.108*
C11	0.3323 (3)	0.6808 (3)	0.6882 (3)	0.0366 (7)
H11	0.3635	0.6302	0.7375	0.044*
C12	0.2286 (3)	0.7115 (3)	0.7109 (3)	0.0369 (7)
C13	0.1625 (3)	0.6770 (3)	0.8099 (3)	0.0422 (7)
H13	0.1778	0.7660	0.8660	0.051*
C14	0.2486 (4)	0.6241 (3)	0.9060 (3)	0.0386 (7)
C15	0.4011 (4)	0.7233 (4)	1.0232 (3)	0.0499 (8)
H15	0.4516	0.8226	1.0415	0.060*
C16	0.4794 (4)	0.6769 (4)	1.1133 (3)	0.0578 (9)
H16	0.5823	0.7437	1.1918	0.069*
C17	0.4030 (5)	0.5317 (5)	1.0847 (4)	0.0574 (9)
C18	0.2544 (5)	0.4297 (4)	0.9701 (4)	0.0602 (9)
H18	0.2064	0.3306	0.9523	0.072*
C19	0.1765 (4)	0.4772 (3)	0.8805 (3)	0.0511 (8)
H19	0.0741	0.4091	0.8020	0.061*
C20	0.0300 (4)	0.7237 (4)	0.5140 (3)	0.0575 (9)
H20	−0.0335	0.6251	0.4561	0.069*
C21	0.1214 (4)	0.9425 (4)	0.5963 (4)	0.0576 (9)
H21	0.1331	1.0325	0.6056	0.069*
C22	−0.1073 (4)	0.5702 (5)	0.7942 (4)	0.0848 (13)
H22A	−0.0758	0.5401	0.8686	0.127*
H22B	−0.2242	0.5026	0.7300	0.127*
H22C	−0.0864	0.6663	0.8301	0.127*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Fe1	0.0423 (3)	0.0416 (3)	0.0379 (3)	0.0215 (2)	0.0203 (2)	0.0153 (2)
F1	0.1239 (19)	0.135 (2)	0.0796 (15)	0.1008 (18)	0.0588 (14)	0.0769 (15)
N1	0.0399 (14)	0.0381 (14)	0.0412 (14)	0.0239 (12)	0.0189 (12)	0.0172 (12)
N2	0.0592 (17)	0.0382 (16)	0.0623 (18)	0.0300 (15)	0.0139 (15)	0.0156 (14)
N3	0.0583 (18)	0.061 (2)	0.0603 (19)	0.0375 (17)	0.0177 (16)	0.0321 (17)
O1	0.0417 (12)	0.0721 (16)	0.0518 (13)	0.0252 (12)	0.0244 (11)	0.0276 (12)
C1	0.0355 (15)	0.0340 (16)	0.0364 (16)	0.0177 (14)	0.0172 (14)	0.0155 (13)
C2	0.0445 (17)	0.0400 (17)	0.0422 (17)	0.0246 (15)	0.0200 (15)	0.0222 (15)
C3	0.0538 (19)	0.0462 (19)	0.0380 (17)	0.0208 (17)	0.0238 (16)	0.0198 (15)
C4	0.058 (2)	0.048 (2)	0.0458 (18)	0.0286 (17)	0.0306 (17)	0.0145 (16)
C5	0.0562 (19)	0.0403 (17)	0.0452 (18)	0.0308 (16)	0.0292 (16)	0.0200 (15)
C6	0.061 (2)	0.078 (3)	0.050 (2)	0.013 (2)	0.025 (2)	−0.009 (2)
C7	0.088 (3)	0.047 (2)	0.068 (3)	0.027 (2)	0.005 (3)	−0.004 (2)
C8	0.077 (3)	0.071 (3)	0.053 (3)	−0.011 (3)	0.026 (2)	0.014 (2)
C9	0.046 (2)	0.115 (4)	0.077 (3)	0.034 (3)	0.015 (2)	0.012 (3)
C10	0.078 (3)	0.089 (3)	0.052 (2)	0.026 (3)	0.006 (2)	0.028 (2)
C11	0.0401 (16)	0.0314 (16)	0.0371 (16)	0.0184 (14)	0.0165 (14)	0.0176 (13)
C12	0.0390 (16)	0.0340 (16)	0.0408 (17)	0.0205 (14)	0.0196 (14)	0.0181 (14)
C13	0.0406 (17)	0.0436 (18)	0.0423 (17)	0.0219 (16)	0.0214 (15)	0.0161 (15)
C14	0.0468 (17)	0.0466 (19)	0.0369 (16)	0.0288 (16)	0.0276 (15)	0.0207 (15)
C15	0.055 (2)	0.047 (2)	0.0429 (18)	0.0261 (17)	0.0226 (17)	0.0151 (16)
C16	0.060 (2)	0.075 (3)	0.0400 (19)	0.041 (2)	0.0210 (17)	0.0202 (19)
C17	0.080 (3)	0.084 (3)	0.055 (2)	0.061 (2)	0.046 (2)	0.045 (2)
C18	0.083 (3)	0.055 (2)	0.072 (2)	0.043 (2)	0.051 (2)	0.041 (2)
C19	0.054 (2)	0.045 (2)	0.054 (2)	0.0228 (17)	0.0297 (17)	0.0242 (17)
C20	0.057 (2)	0.046 (2)	0.049 (2)	0.0229 (18)	0.0118 (18)	0.0199 (17)
C21	0.064 (2)	0.049 (2)	0.074 (2)	0.039 (2)	0.031 (2)	0.033 (2)
C22	0.057 (2)	0.115 (4)	0.098 (3)	0.045 (2)	0.053 (2)	0.045 (3)

Geometric parameters (Å, º)

Fe1—C10	2.020 (4)	C6—C7	1.410 (6)
Fe1—C6	2.021 (4)	C6—H6	0.9300
Fe1—C5	2.022 (3)	C7—C8	1.414 (6)
Fe1—C7	2.027 (4)	C7—H7	0.9300
Fe1—C1	2.028 (3)	C8—C9	1.368 (6)
Fe1—C8	2.030 (4)	C8—H8	0.9300
Fe1—C9	2.032 (4)	C9—C10	1.361 (6)
Fe1—C2	2.036 (3)	C9—H9	0.9300
Fe1—C4	2.041 (3)	C10—H10	0.9300
Fe1—C3	2.043 (3)	C11—C12	1.321 (4)
F1—C17	1.363 (4)	C11—H11	0.9300
N1—C20	1.319 (4)	C12—C13	1.510 (4)
N1—N2	1.360 (3)	C13—C14	1.513 (4)
N1—C12	1.440 (3)	C13—H13	0.9800
N2—C21	1.317 (4)	C14—C19	1.380 (4)
N3—C20	1.311 (4)	C14—C15	1.383 (4)
N3—C21	1.338 (4)	C15—C16	1.379 (4)
O1—C13	1.417 (3)	C15—H15	0.9300
O1—C22	1.428 (4)	C16—C17	1.354 (5)
C1—C2	1.429 (4)	C16—H16	0.9300
C1—C5	1.436 (4)	C17—C18	1.358 (5)
C1—C11	1.457 (4)	C18—C19	1.383 (4)
C2—C3	1.404 (4)	C18—H18	0.9300
C2—H2	0.9300	C19—H19	0.9300
C3—C4	1.407 (4)	C20—H20	0.9300
C3—H3	0.9300	C21—H21	0.9300
C4—C5	1.410 (4)	C22—H22A	0.9600
C4—H4	0.9300	C22—H22B	0.9600
C5—H5	0.9300	C22—H22C	0.9600
C6—C10	1.359 (6)
C10—Fe1—C6	39.31 (17)	C1—C5—Fe1	69.46 (16)
C10—Fe1—C5	107.08 (16)	C4—C5—H5	125.8
C6—Fe1—C5	127.01 (17)	C1—C5—H5	125.8
C10—Fe1—C7	67.26 (19)	Fe1—C5—H5	125.9
C6—Fe1—C7	40.79 (17)	C10—C6—C7	108.0 (4)
C5—Fe1—C7	166.19 (19)	C10—C6—Fe1	70.3 (2)
C10—Fe1—C1	117.05 (16)	C7—C6—Fe1	69.8 (2)
C6—Fe1—C1	107.32 (14)	C10—C6—H6	126.0
C5—Fe1—C1	41.52 (11)	C7—C6—H6	126.0
C7—Fe1—C1	128.43 (18)	Fe1—C6—H6	125.5
C10—Fe1—C8	66.43 (18)	C6—C7—C8	105.9 (4)
C6—Fe1—C8	67.60 (16)	C6—C7—Fe1	69.4 (2)
C5—Fe1—C8	150.2 (2)	C8—C7—Fe1	69.7 (2)
C7—Fe1—C8	40.79 (18)	C6—C7—H7	127.1
C1—Fe1—C8	168.1 (2)	C8—C7—H7	127.1
C10—Fe1—C9	39.25 (18)	Fe1—C7—H7	125.4
C6—Fe1—C9	66.45 (18)	C9—C8—C7	107.9 (4)
C5—Fe1—C9	116.94 (19)	C9—C8—Fe1	70.4 (2)
C7—Fe1—C9	67.3 (2)	C7—C8—Fe1	69.5 (2)
C1—Fe1—C9	149.9 (2)	C9—C8—H8	126.0
C8—Fe1—C9	39.37 (18)	C7—C8—H8	126.0
C10—Fe1—C2	151.90 (19)	Fe1—C8—H8	125.6
C6—Fe1—C2	119.78 (17)	C10—C9—C8	108.7 (4)
C5—Fe1—C2	68.78 (12)	C10—C9—Fe1	69.9 (2)
C7—Fe1—C2	109.85 (15)	C8—C9—Fe1	70.2 (2)
C1—Fe1—C2	41.17 (11)	C10—C9—H9	125.6
C8—Fe1—C2	130.9 (2)	C8—C9—H9	125.6
C9—Fe1—C2	167.9 (2)	Fe1—C9—H9	125.8
C10—Fe1—C4	127.8 (2)	C6—C10—C9	109.5 (5)
C6—Fe1—C4	164.6 (2)	C6—C10—Fe1	70.4 (2)
C5—Fe1—C4	40.60 (12)	C9—C10—Fe1	70.9 (2)
C7—Fe1—C4	152.8 (2)	C6—C10—H10	125.3
C1—Fe1—C4	69.12 (12)	C9—C10—H10	125.3
C8—Fe1—C4	118.69 (17)	Fe1—C10—H10	125.1
C9—Fe1—C4	108.65 (16)	C12—C11—C1	130.4 (3)
C2—Fe1—C4	68.08 (13)	C12—C11—H11	114.8
C10—Fe1—C3	166.0 (2)	C1—C11—H11	114.8
C6—Fe1—C3	153.85 (19)	C11—C12—N1	121.1 (2)
C5—Fe1—C3	68.23 (12)	C11—C12—C13	126.8 (3)
C7—Fe1—C3	120.24 (17)	N1—C12—C13	112.2 (2)
C1—Fe1—C3	68.83 (11)	O1—C13—C12	105.2 (2)
C8—Fe1—C3	110.63 (15)	O1—C13—C14	112.6 (2)
C9—Fe1—C3	129.87 (18)	C12—C13—C14	113.9 (2)
C2—Fe1—C3	40.28 (11)	O1—C13—H13	108.3
C4—Fe1—C3	40.29 (12)	C12—C13—H13	108.3
C20—N1—N2	108.8 (2)	C14—C13—H13	108.3
C20—N1—C12	129.2 (3)	C19—C14—C15	118.5 (3)
N2—N1—C12	121.7 (2)	C19—C14—C13	121.3 (3)
C21—N2—N1	101.5 (3)	C15—C14—C13	120.2 (3)
C20—N3—C21	101.3 (3)	C16—C15—C14	120.9 (3)
C13—O1—C22	113.6 (2)	C16—C15—H15	119.6
C2—C1—C5	106.3 (2)	C14—C15—H15	119.6
C2—C1—C11	130.9 (3)	C17—C16—C15	118.5 (3)
C5—C1—C11	122.5 (3)	C17—C16—H16	120.8
C2—C1—Fe1	69.71 (15)	C15—C16—H16	120.8
C5—C1—Fe1	69.01 (16)	C16—C17—C18	122.9 (3)
C11—C1—Fe1	121.55 (19)	C16—C17—F1	118.5 (3)
C3—C2—C1	108.6 (3)	C18—C17—F1	118.5 (3)
C3—C2—Fe1	70.16 (17)	C17—C18—C19	118.2 (3)
C1—C2—Fe1	69.13 (16)	C17—C18—H18	120.9
C3—C2—H2	125.7	C19—C18—H18	120.9
C1—C2—H2	125.7	C14—C19—C18	121.0 (3)
Fe1—C2—H2	126.6	C14—C19—H19	119.5
C2—C3—C4	108.5 (3)	C18—C19—H19	119.5
C2—C3—Fe1	69.57 (16)	N3—C20—N1	112.2 (3)
C4—C3—Fe1	69.76 (17)	N3—C20—H20	123.9
C2—C3—H3	125.7	N1—C20—H20	123.9
C4—C3—H3	125.7	N2—C21—N3	116.2 (3)
Fe1—C3—H3	126.5	N2—C21—H21	121.9
C3—C4—C5	108.1 (3)	N3—C21—H21	121.9
C3—C4—Fe1	69.95 (17)	O1—C22—H22A	109.5
C5—C4—Fe1	68.98 (17)	O1—C22—H22B	109.5
C3—C4—H4	125.9	H22A—C22—H22B	109.5
C5—C4—H4	125.9	O1—C22—H22C	109.5
Fe1—C4—H4	126.7	H22A—C22—H22C	109.5
C4—C5—C1	108.4 (3)	H22B—C22—H22C	109.5
C4—C5—Fe1	70.43 (18)
C20—N1—N2—C21	−0.2 (3)	C1—Fe1—C6—C7	−129.4 (3)
C12—N1—N2—C21	−175.1 (3)	C8—Fe1—C6—C7	39.1 (3)
C10—Fe1—C1—C2	157.0 (2)	C9—Fe1—C6—C7	82.0 (3)
C6—Fe1—C1—C2	115.7 (2)	C2—Fe1—C6—C7	−86.3 (3)
C5—Fe1—C1—C2	−117.5 (2)	C4—Fe1—C6—C7	156.4 (5)
C7—Fe1—C1—C2	75.6 (3)	C3—Fe1—C6—C7	−52.3 (5)
C8—Fe1—C1—C2	52.8 (7)	C10—C6—C7—C8	−0.3 (4)
C9—Fe1—C1—C2	−171.6 (3)	Fe1—C6—C7—C8	−60.5 (3)
C4—Fe1—C1—C2	−80.17 (18)	C10—C6—C7—Fe1	60.2 (3)
C3—Fe1—C1—C2	−36.87 (17)	C10—Fe1—C7—C6	−37.0 (3)
C10—Fe1—C1—C5	−85.5 (3)	C5—Fe1—C7—C6	31.2 (8)
C6—Fe1—C1—C5	−126.8 (2)	C1—Fe1—C7—C6	70.3 (3)
C7—Fe1—C1—C5	−166.9 (2)	C8—Fe1—C7—C6	−116.8 (4)
C8—Fe1—C1—C5	170.3 (6)	C9—Fe1—C7—C6	−79.7 (3)
C9—Fe1—C1—C5	−54.0 (4)	C2—Fe1—C7—C6	112.9 (3)
C2—Fe1—C1—C5	117.5 (2)	C4—Fe1—C7—C6	−166.6 (3)
C4—Fe1—C1—C5	37.34 (17)	C3—Fe1—C7—C6	156.2 (3)
C3—Fe1—C1—C5	80.65 (18)	C10—Fe1—C7—C8	79.7 (3)
C10—Fe1—C1—C11	30.7 (3)	C6—Fe1—C7—C8	116.8 (4)
C6—Fe1—C1—C11	−10.7 (3)	C5—Fe1—C7—C8	147.9 (6)
C5—Fe1—C1—C11	116.1 (3)	C1—Fe1—C7—C8	−173.0 (3)
C7—Fe1—C1—C11	−50.7 (3)	C9—Fe1—C7—C8	37.0 (2)
C8—Fe1—C1—C11	−73.5 (7)	C2—Fe1—C7—C8	−130.3 (3)
C9—Fe1—C1—C11	62.1 (4)	C4—Fe1—C7—C8	−49.8 (5)
C2—Fe1—C1—C11	−126.3 (3)	C3—Fe1—C7—C8	−87.1 (3)
C4—Fe1—C1—C11	153.5 (3)	C6—C7—C8—C9	0.1 (4)
C3—Fe1—C1—C11	−163.2 (3)	Fe1—C7—C8—C9	−60.2 (3)
C5—C1—C2—C3	−0.4 (3)	C6—C7—C8—Fe1	60.3 (3)
C11—C1—C2—C3	173.9 (3)	C10—Fe1—C8—C9	36.9 (3)
Fe1—C1—C2—C3	59.2 (2)	C6—Fe1—C8—C9	79.7 (3)
C5—C1—C2—Fe1	−59.61 (19)	C5—Fe1—C8—C9	−46.4 (4)
C11—C1—C2—Fe1	114.7 (3)	C7—Fe1—C8—C9	118.8 (4)
C10—Fe1—C2—C3	−167.6 (3)	C1—Fe1—C8—C9	146.5 (7)
C6—Fe1—C2—C3	157.6 (2)	C2—Fe1—C8—C9	−169.6 (3)
C5—Fe1—C2—C3	−80.96 (18)	C4—Fe1—C8—C9	−84.7 (3)
C7—Fe1—C2—C3	113.7 (2)	C3—Fe1—C8—C9	−128.4 (3)
C1—Fe1—C2—C3	−120.1 (2)	C10—Fe1—C8—C7	−82.0 (3)
C8—Fe1—C2—C3	72.5 (3)	C6—Fe1—C8—C7	−39.1 (3)
C9—Fe1—C2—C3	39.4 (8)	C5—Fe1—C8—C7	−165.3 (3)
C4—Fe1—C2—C3	−37.16 (18)	C1—Fe1—C8—C7	27.7 (8)
C10—Fe1—C2—C1	−47.5 (4)	C9—Fe1—C8—C7	−118.8 (4)
C6—Fe1—C2—C1	−82.3 (2)	C2—Fe1—C8—C7	71.6 (3)
C5—Fe1—C2—C1	39.10 (16)	C4—Fe1—C8—C7	156.5 (3)
C7—Fe1—C2—C1	−126.2 (2)	C3—Fe1—C8—C7	112.8 (3)
C8—Fe1—C2—C1	−167.4 (2)	C7—C8—C9—C10	0.1 (5)
C9—Fe1—C2—C1	159.5 (8)	Fe1—C8—C9—C10	−59.5 (3)
C4—Fe1—C2—C1	82.90 (18)	C7—C8—C9—Fe1	59.6 (3)
C3—Fe1—C2—C1	120.1 (2)	C6—Fe1—C9—C10	36.8 (3)
C1—C2—C3—C4	0.5 (3)	C5—Fe1—C9—C10	−84.2 (3)
Fe1—C2—C3—C4	59.0 (2)	C7—Fe1—C9—C10	81.3 (3)
C1—C2—C3—Fe1	−58.6 (2)	C1—Fe1—C9—C10	−47.2 (5)
C10—Fe1—C3—C2	155.3 (6)	C8—Fe1—C9—C10	119.7 (4)
C6—Fe1—C3—C2	−48.7 (4)	C2—Fe1—C9—C10	160.2 (7)
C5—Fe1—C3—C2	82.43 (18)	C4—Fe1—C9—C10	−127.5 (3)
C7—Fe1—C3—C2	−85.4 (3)	C3—Fe1—C9—C10	−167.4 (3)
C1—Fe1—C3—C2	37.66 (17)	C10—Fe1—C9—C8	−119.7 (4)
C8—Fe1—C3—C2	−129.6 (3)	C6—Fe1—C9—C8	−82.9 (3)
C9—Fe1—C3—C2	−170.0 (3)	C5—Fe1—C9—C8	156.1 (3)
C4—Fe1—C3—C2	119.9 (3)	C7—Fe1—C9—C8	−38.3 (3)
C10—Fe1—C3—C4	35.3 (7)	C1—Fe1—C9—C8	−166.9 (3)
C6—Fe1—C3—C4	−168.6 (3)	C2—Fe1—C9—C8	40.5 (9)
C5—Fe1—C3—C4	−37.51 (18)	C4—Fe1—C9—C8	112.8 (3)
C7—Fe1—C3—C4	154.6 (2)	C3—Fe1—C9—C8	72.9 (3)
C1—Fe1—C3—C4	−82.28 (19)	C7—C6—C10—C9	0.4 (5)
C8—Fe1—C3—C4	110.4 (3)	Fe1—C6—C10—C9	60.3 (3)
C9—Fe1—C3—C4	70.1 (3)	C7—C6—C10—Fe1	−59.9 (3)
C2—Fe1—C3—C4	−119.9 (3)	C8—C9—C10—C6	−0.3 (5)
C2—C3—C4—C5	−0.3 (3)	Fe1—C9—C10—C6	−60.0 (3)
Fe1—C3—C4—C5	58.6 (2)	C8—C9—C10—Fe1	59.7 (3)
C2—C3—C4—Fe1	−58.9 (2)	C5—Fe1—C10—C6	−128.2 (3)
C10—Fe1—C4—C3	−169.8 (2)	C7—Fe1—C10—C6	38.4 (3)
C6—Fe1—C4—C3	160.9 (5)	C1—Fe1—C10—C6	−84.5 (3)
C5—Fe1—C4—C3	119.7 (3)	C8—Fe1—C10—C6	82.9 (3)
C7—Fe1—C4—C3	−53.9 (4)	C9—Fe1—C10—C6	119.9 (5)
C1—Fe1—C4—C3	81.50 (19)	C2—Fe1—C10—C6	−51.4 (5)
C8—Fe1—C4—C3	−88.6 (3)	C4—Fe1—C10—C6	−168.2 (3)
C9—Fe1—C4—C3	−130.4 (3)	C3—Fe1—C10—C6	163.6 (5)
C2—Fe1—C4—C3	37.15 (18)	C6—Fe1—C10—C9	−119.9 (5)
C10—Fe1—C4—C5	70.5 (3)	C5—Fe1—C10—C9	111.9 (3)
C6—Fe1—C4—C5	41.2 (6)	C7—Fe1—C10—C9	−81.5 (3)
C7—Fe1—C4—C5	−173.6 (3)	C1—Fe1—C10—C9	155.6 (3)
C1—Fe1—C4—C5	−38.17 (18)	C8—Fe1—C10—C9	−37.0 (3)
C8—Fe1—C4—C5	151.7 (3)	C2—Fe1—C10—C9	−171.3 (3)
C9—Fe1—C4—C5	109.9 (3)	C4—Fe1—C10—C9	72.0 (4)
C2—Fe1—C4—C5	−82.52 (19)	C3—Fe1—C10—C9	43.7 (8)
C3—Fe1—C4—C5	−119.7 (3)	C2—C1—C11—C12	12.4 (5)
C3—C4—C5—C1	0.1 (3)	C5—C1—C11—C12	−174.1 (3)
Fe1—C4—C5—C1	59.3 (2)	Fe1—C1—C11—C12	102.1 (3)
C3—C4—C5—Fe1	−59.2 (2)	C1—C11—C12—N1	3.6 (5)
C2—C1—C5—C4	0.2 (3)	C1—C11—C12—C13	−178.0 (3)
C11—C1—C5—C4	−174.7 (3)	C20—N1—C12—C11	85.1 (4)
Fe1—C1—C5—C4	−59.9 (2)	N2—N1—C12—C11	−101.2 (3)
C2—C1—C5—Fe1	60.06 (19)	C20—N1—C12—C13	−93.5 (4)
C11—C1—C5—Fe1	−114.8 (3)	N2—N1—C12—C13	80.2 (3)
C10—Fe1—C5—C4	−128.8 (3)	C22—O1—C13—C12	−155.5 (3)
C6—Fe1—C5—C4	−167.3 (2)	C22—O1—C13—C14	79.9 (3)
C7—Fe1—C5—C4	167.6 (6)	C11—C12—C13—O1	−113.5 (3)
C1—Fe1—C5—C4	119.4 (3)	N1—C12—C13—O1	65.0 (3)
C8—Fe1—C5—C4	−56.6 (4)	C11—C12—C13—C14	10.3 (4)
C9—Fe1—C5—C4	−87.6 (3)	N1—C12—C13—C14	−171.2 (2)
C2—Fe1—C5—C4	80.7 (2)	O1—C13—C14—C19	19.7 (4)
C3—Fe1—C5—C4	37.23 (19)	C12—C13—C14—C19	−100.0 (3)
C10—Fe1—C5—C1	111.8 (2)	O1—C13—C14—C15	−159.3 (3)
C6—Fe1—C5—C1	73.2 (3)	C12—C13—C14—C15	81.0 (3)
C7—Fe1—C5—C1	48.2 (7)	C19—C14—C15—C16	−0.4 (4)
C8—Fe1—C5—C1	−176.0 (3)	C13—C14—C15—C16	178.6 (3)
C9—Fe1—C5—C1	152.9 (2)	C14—C15—C16—C17	−0.3 (5)
C2—Fe1—C5—C1	−38.78 (16)	C15—C16—C17—C18	1.3 (5)
C4—Fe1—C5—C1	−119.4 (3)	C15—C16—C17—F1	−179.0 (3)
C3—Fe1—C5—C1	−82.21 (18)	C16—C17—C18—C19	−1.5 (5)
C5—Fe1—C6—C10	70.1 (3)	F1—C17—C18—C19	178.8 (3)
C7—Fe1—C6—C10	−118.8 (4)	C15—C14—C19—C18	0.2 (4)
C1—Fe1—C6—C10	111.8 (3)	C13—C14—C19—C18	−178.8 (3)
C8—Fe1—C6—C10	−79.7 (3)	C17—C18—C19—C14	0.7 (5)
C9—Fe1—C6—C10	−36.8 (3)	C21—N3—C20—N1	0.1 (4)
C2—Fe1—C6—C10	154.9 (3)	N2—N1—C20—N3	0.1 (4)
C4—Fe1—C6—C10	37.7 (7)	C12—N1—C20—N3	174.4 (3)
C3—Fe1—C6—C10	−171.1 (3)	N1—N2—C21—N3	0.3 (4)
C10—Fe1—C6—C7	118.8 (4)	C20—N3—C21—N2	−0.3 (4)
C5—Fe1—C6—C7	−171.1 (3)