N-Benzyl­idene-4-(ferrocen­yl)-5-(1H-1,2,4-triazol-1-yl)-1,3-thia­zol-2-amine

In search of potent fungicidal agents, the title compound, [Fe(C₅H₅)(C₁₇H₁₂N₅S)], has been synthesized and its crystal structure determined. The dihedral angles between the planes of the phenyl and thia­zole rings and between the thia­zole and triazole rings are 42.19 (13) and 81.15 (12)°, respectively.

Key indicators

• Single-crystal X-ray study
• T = 294 K
• Mean [sigma](C-C) = 0.006 Å
• R factor = 0.038
• wR factor = 0.103
• Data-to-parameter ratio = 13.0

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C1     -   C2      ..       6.93 su
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         C2
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         C3
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         C4
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C22
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        Fe1
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C17
PLAT322_ALERT_2_C Check Hybridisation of  S1     in Main Residue .          ?

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   8 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
   8 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

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S1. Comment

Ferrocene-containing organic compounds often exhibit biological activity (Biot et al., 2000; Fang et al., 2003a,b). Thiazoles and their derivatives are found to be associated with various biological activities, such as antibacterial, antifungal and anti-inflammatory activities (Gusmeroli et al., 2003; Wilson et al., 2001). Triazole antifungals are known as potent inhibitors of cytochrome P450 monooxygenase in the process of fungal biosynthesis of ergosterol, which is an important constituent of fungal cell membranes (Miyauchi et al., 1995). In order to find out more biologically active thiazole compounds, the title compound, (I), was synthesized and its crystal structure determined (Fig. 1).

The title compound contains three planes: (i) the phenyl ring C17–C22; (ii) the thiazole ring C11/C12/S1/C15/N4; (iii) the triazole ring N1/C13/N3/N2/C14. The dihedral angles between planes i and ii, and between planes ii and iii are 42.19 (13) and 81.15 (12)°, respectively.

S2. Experimental

2-Amino-4-(ferrocenyl)-5-(1H-1,2,4-triazol-1-yl)-1,3-thiazole (Shao et al., 2004) (0.7 g, 2 mmol) and benzaldehyde (0.21 g, 2 mmol) were dissolved in benzene (10 ml). One drop of piperidine was added to the mixture solution. The solution was heated and refluxed for ca 1 h until no water appeared. The solution was then concentrated and purified by silica column chromatography (eluent: ethyl acetate–petroleum ether, 1:1). Single crystals were obtained by evaporation of the solvent (m.p. 438–439 K; yield 88%). Analysis calculated for C₂₂H₁₇FeN₅S: C 60.15, H 3.90, N 15.94%; found: C 60.27, H 4.04, N 16.03%. ¹H NMR (CDCl₃): δ 9.02 (s, 1H), 8.30 (s, 1H), 8.25 (s, 1H), 7.63–7.51(m, 5H), 4.27 (s, 2H), 4.26 (s, 2H), 4.12 (s, 5H).

S3. Refinement

All H atoms were placed in calculated positions, with C—H = 0.93 Å, and included in the final cycles of refinement using a riding model, with U_iso(H) = 1.2U_eq(C).

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. View of the title compound, with displacement ellipsoids drawn at the 30% probability level.

N-benzylidene-4-(ferrocenyl)-5-(1H-1,2,4-triazol-1-yl)-1,3-thiazol-2-amine

Crystal data

[Fe(C5H5)(C17H12N5S)]	Z = 2
Mr = 439.32	F(000) = 452
Triclinic, P1	Dx = 1.495 Mg m^−3
Hall symbol: -P 1	Melting point: 438 K
a = 8.826 (4) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.608 (5) Å	Cell parameters from 1939 reflections
c = 11.619 (5) Å	θ = 2.3–22.2°
α = 64.982 (7)°	µ = 0.90 mm^−1
β = 83.064 (8)°	T = 294 K
γ = 83.425 (7)°	Plate, orange
V = 976.0 (8) Å^3	0.22 × 0.20 × 0.18 mm

Data collection

Bruker SMART CCD area-detector diffractometer	3425 independent reflections
Radiation source: fine-focus sealed tube	2557 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.025
ϕ and ω scans	θmax = 25.0°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→8
Tmin = 0.817, Tmax = 0.851	k = −12→12
4998 measured reflections	l = −11→13

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)] = 0.038	H-atom parameters constrained
wR(F^2) = 0.103	w = 1/[σ^2(Fo^2) + (0.0511P)^2 + 0.1365P] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max = 0.001
3425 reflections	Δρmax = 0.27 e Å^−3
263 parameters	Δρmin = −0.26 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: 0.057 (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	0.18850 (5)	0.12820 (4)	0.68689 (4)	0.04269 (18)
S1	0.73144 (9)	0.32022 (8)	0.45286 (7)	0.0502 (2)
N1	0.6902 (4)	0.1662 (4)	0.9003 (3)	0.0815 (10)
N2	0.6675 (4)	0.0677 (3)	0.7645 (3)	0.0729 (9)
N3	0.6410 (3)	0.2095 (3)	0.7079 (2)	0.0466 (6)
N4	0.4458 (3)	0.3926 (2)	0.4158 (2)	0.0442 (6)
N5	0.6021 (3)	0.4703 (3)	0.2247 (2)	0.0524 (7)
C1	0.3251 (5)	−0.0202 (4)	0.6516 (4)	0.0706 (10)
H1	0.4265	−0.0107	0.6183	0.085*
C2	0.1959 (7)	0.0165 (4)	0.5810 (4)	0.0930 (16)
H2	0.1953	0.0531	0.4928	0.112*
C3	0.0660 (5)	−0.0137 (5)	0.6715 (7)	0.0960 (15)
H3	−0.0360	−0.0006	0.6537	0.115*
C4	0.1201 (7)	−0.0658 (4)	0.7893 (5)	0.0943 (15)
H4	0.0597	−0.0929	0.8660	0.113*
C5	0.2751 (6)	−0.0719 (4)	0.7775 (4)	0.0764 (11)
H5	0.3375	−0.1061	0.8448	0.092*
C6	0.1619 (3)	0.3375 (3)	0.5748 (3)	0.0486 (7)
H6	0.1442	0.3791	0.4889	0.058*
C7	0.0492 (4)	0.2991 (3)	0.6778 (3)	0.0578 (9)
H7	−0.0560	0.3104	0.6714	0.069*
C8	0.1218 (4)	0.2410 (3)	0.7915 (3)	0.0560 (8)
H8	0.0732	0.2079	0.8733	0.067*
C9	0.2825 (3)	0.2414 (3)	0.7604 (3)	0.0474 (7)
H9	0.3573	0.2083	0.8181	0.057*
C10	0.3086 (3)	0.3013 (3)	0.6255 (3)	0.0403 (6)
C11	0.4528 (3)	0.3215 (3)	0.5457 (2)	0.0390 (6)
C12	0.5969 (3)	0.2778 (3)	0.5822 (3)	0.0407 (7)
C13	0.6554 (4)	0.2647 (4)	0.7900 (3)	0.0600 (9)
H13	0.6425	0.3594	0.7715	0.072*
C14	0.6950 (5)	0.0506 (5)	0.8793 (4)	0.0909 (14)
H14	0.7168	−0.0375	0.9429	0.109*
C15	0.5809 (4)	0.3985 (3)	0.3560 (3)	0.0455 (7)
C16	0.7049 (4)	0.4313 (3)	0.1607 (3)	0.0605 (9)
H16	0.7636	0.3488	0.2018	0.073*
C17	0.7366 (4)	0.5107 (3)	0.0231 (3)	0.0536 (8)
C18	0.6626 (4)	0.6396 (4)	−0.0414 (3)	0.0655 (9)
H18	0.5875	0.6760	0.0017	0.079*
C19	0.6997 (5)	0.7142 (4)	−0.1696 (3)	0.0784 (11)
H19	0.6494	0.8009	−0.2128	0.094*
C20	0.8099 (5)	0.6617 (4)	−0.2338 (3)	0.0734 (11)
H20	0.8358	0.7133	−0.3200	0.088*
C21	0.8813 (6)	0.5347 (4)	−0.1720 (4)	0.0887 (14)
H21	0.9550	0.4982	−0.2160	0.106*
C22	0.8450 (6)	0.4589 (4)	−0.0434 (4)	0.0881 (14)
H22	0.8947	0.3716	−0.0015	0.106*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Fe1	0.0433 (3)	0.0417 (3)	0.0448 (3)	−0.00659 (18)	−0.00267 (19)	−0.0190 (2)
S1	0.0476 (5)	0.0508 (5)	0.0458 (5)	−0.0062 (3)	0.0043 (3)	−0.0153 (4)
N1	0.074 (2)	0.107 (3)	0.0471 (19)	0.001 (2)	−0.0150 (16)	−0.0146 (19)
N2	0.079 (2)	0.0517 (17)	0.062 (2)	0.0051 (15)	−0.0122 (16)	0.0009 (15)
N3	0.0376 (13)	0.0494 (15)	0.0422 (14)	−0.0002 (11)	−0.0042 (11)	−0.0092 (12)
N4	0.0504 (15)	0.0447 (14)	0.0365 (13)	−0.0090 (11)	−0.0048 (12)	−0.0141 (11)
N5	0.0643 (17)	0.0507 (16)	0.0400 (15)	−0.0139 (13)	0.0013 (13)	−0.0157 (13)
C1	0.076 (3)	0.055 (2)	0.090 (3)	−0.0050 (18)	0.010 (2)	−0.043 (2)
C2	0.192 (5)	0.050 (2)	0.050 (2)	−0.009 (3)	−0.030 (3)	−0.0276 (19)
C3	0.081 (3)	0.069 (3)	0.161 (5)	−0.016 (2)	−0.032 (3)	−0.061 (3)
C4	0.120 (4)	0.057 (2)	0.096 (4)	−0.032 (3)	0.040 (3)	−0.028 (2)
C5	0.107 (3)	0.050 (2)	0.067 (3)	0.013 (2)	−0.020 (2)	−0.0198 (19)
C6	0.0479 (18)	0.0430 (17)	0.0529 (19)	0.0013 (13)	−0.0109 (15)	−0.0174 (14)
C7	0.0377 (17)	0.060 (2)	0.080 (2)	0.0034 (14)	−0.0009 (17)	−0.0352 (19)
C8	0.056 (2)	0.064 (2)	0.055 (2)	−0.0100 (16)	0.0115 (16)	−0.0339 (17)
C9	0.0474 (18)	0.0569 (19)	0.0436 (18)	−0.0092 (14)	−0.0022 (14)	−0.0253 (15)
C10	0.0426 (16)	0.0362 (15)	0.0436 (17)	−0.0061 (12)	−0.0016 (13)	−0.0175 (13)
C11	0.0491 (17)	0.0342 (15)	0.0352 (15)	−0.0063 (12)	−0.0046 (13)	−0.0145 (12)
C12	0.0419 (16)	0.0414 (15)	0.0349 (15)	−0.0041 (12)	−0.0008 (13)	−0.0123 (13)
C13	0.0491 (19)	0.081 (2)	0.047 (2)	−0.0002 (17)	−0.0111 (16)	−0.0239 (19)
C14	0.083 (3)	0.082 (3)	0.065 (3)	0.009 (2)	−0.023 (2)	0.013 (2)
C15	0.059 (2)	0.0404 (16)	0.0368 (16)	−0.0089 (14)	−0.0028 (14)	−0.0147 (13)
C16	0.090 (3)	0.0422 (18)	0.0459 (19)	−0.0128 (17)	0.0075 (18)	−0.0168 (16)
C17	0.080 (2)	0.0418 (18)	0.0387 (17)	−0.0149 (16)	0.0077 (16)	−0.0174 (15)
C18	0.074 (2)	0.071 (2)	0.048 (2)	0.0012 (19)	0.0017 (18)	−0.0238 (18)
C19	0.102 (3)	0.069 (3)	0.050 (2)	0.009 (2)	−0.008 (2)	−0.0149 (19)
C20	0.118 (3)	0.064 (2)	0.0383 (19)	−0.019 (2)	0.004 (2)	−0.0204 (18)
C21	0.142 (4)	0.063 (3)	0.055 (2)	0.003 (3)	0.023 (2)	−0.029 (2)
C22	0.146 (4)	0.047 (2)	0.055 (2)	0.006 (2)	0.021 (2)	−0.0160 (18)

Geometric parameters (Å, º)

Fe1—C4	2.013 (4)	C4—C5	1.355 (6)
Fe1—C1	2.022 (3)	C4—H4	0.9300
Fe1—C3	2.028 (4)	C5—H5	0.9300
Fe1—C2	2.029 (3)	C6—C7	1.407 (4)
Fe1—C9	2.031 (3)	C6—C10	1.432 (4)
Fe1—C5	2.033 (4)	C6—H6	0.9300
Fe1—C8	2.038 (3)	C7—C8	1.401 (5)
Fe1—C10	2.040 (3)	C7—H7	0.9300
Fe1—C7	2.042 (3)	C8—C9	1.420 (4)
Fe1—C6	2.047 (3)	C8—H8	0.9300
S1—C12	1.729 (3)	C9—C10	1.420 (4)
S1—C15	1.743 (3)	C9—H9	0.9300
N1—C13	1.310 (4)	C10—C11	1.461 (4)
N1—C14	1.343 (6)	C11—C12	1.357 (4)
N2—C14	1.317 (5)	C13—H13	0.9300
N2—N3	1.368 (4)	C14—H14	0.9300
N3—C13	1.337 (4)	C16—C17	1.466 (4)
N3—C12	1.410 (3)	C16—H16	0.9300
N4—C15	1.299 (4)	C17—C22	1.369 (5)
N4—C11	1.379 (3)	C17—C18	1.380 (4)
N5—C16	1.249 (4)	C18—C19	1.377 (5)
N5—C15	1.386 (4)	C18—H18	0.9300
C1—C5	1.363 (5)	C19—C20	1.365 (5)
C1—C2	1.407 (6)	C19—H19	0.9300
C1—H1	0.9300	C20—C21	1.350 (5)
C2—C3	1.424 (6)	C20—H20	0.9300
C2—H2	0.9300	C21—C22	1.381 (5)
C3—C4	1.365 (6)	C21—H21	0.9300
C3—H3	0.9300	C22—H22	0.9300
C4—Fe1—C1	66.63 (17)	C3—C4—H4	125.1
C4—Fe1—C3	39.48 (19)	Fe1—C4—H4	124.4
C1—Fe1—C3	68.04 (18)	C4—C5—C1	109.3 (4)
C4—Fe1—C2	67.32 (18)	C4—C5—Fe1	69.7 (2)
C1—Fe1—C2	40.63 (17)	C1—C5—Fe1	70.0 (2)
C3—Fe1—C2	41.11 (19)	C4—C5—H5	125.3
C4—Fe1—C9	124.49 (19)	C1—C5—H5	125.3
C1—Fe1—C9	117.82 (15)	Fe1—C5—H5	126.6
C3—Fe1—C9	161.8 (2)	C7—C6—C10	108.0 (3)
C2—Fe1—C9	153.6 (2)	C7—C6—Fe1	69.67 (18)
C4—Fe1—C5	39.12 (17)	C10—C6—Fe1	69.22 (16)
C1—Fe1—C5	39.28 (15)	C7—C6—H6	126.0
C3—Fe1—C5	66.41 (19)	C10—C6—H6	126.0
C2—Fe1—C5	66.84 (16)	Fe1—C6—H6	126.7
C9—Fe1—C5	106.33 (15)	C8—C7—C6	108.6 (3)
C4—Fe1—C8	107.50 (16)	C8—C7—Fe1	69.76 (18)
C1—Fe1—C8	151.76 (16)	C6—C7—Fe1	70.08 (17)
C3—Fe1—C8	126.18 (19)	C8—C7—H7	125.7
C2—Fe1—C8	165.2 (2)	C6—C7—H7	125.7
C9—Fe1—C8	40.86 (12)	Fe1—C7—H7	126.0
C5—Fe1—C8	118.61 (16)	C7—C8—C9	108.3 (3)
C4—Fe1—C10	161.5 (2)	C7—C8—Fe1	70.07 (18)
C1—Fe1—C10	107.75 (14)	C9—C8—Fe1	69.33 (17)
C3—Fe1—C10	157.0 (2)	C7—C8—H8	125.9
C2—Fe1—C10	120.84 (17)	C9—C8—H8	125.9
C9—Fe1—C10	40.82 (11)	Fe1—C8—H8	126.3
C5—Fe1—C10	125.53 (16)	C10—C9—C8	108.0 (3)
C8—Fe1—C10	68.57 (12)	C10—C9—Fe1	69.92 (16)
C4—Fe1—C7	120.95 (18)	C8—C9—Fe1	69.81 (17)
C1—Fe1—C7	166.72 (16)	C10—C9—H9	126.0
C3—Fe1—C7	110.10 (16)	C8—C9—H9	126.0
C2—Fe1—C7	129.34 (18)	Fe1—C9—H9	125.8
C9—Fe1—C7	68.29 (13)	C9—C10—C6	107.2 (3)
C5—Fe1—C7	153.25 (16)	C9—C10—C11	129.7 (3)
C8—Fe1—C7	40.16 (13)	C6—C10—C11	123.2 (3)
C10—Fe1—C7	68.50 (13)	C9—C10—Fe1	69.26 (16)
C4—Fe1—C6	155.9 (2)	C6—C10—Fe1	69.75 (16)
C1—Fe1—C6	128.75 (15)	C11—C10—Fe1	124.38 (19)
C3—Fe1—C6	122.90 (19)	C12—C11—N4	113.9 (2)
C2—Fe1—C6	110.80 (15)	C12—C11—C10	128.5 (3)
C9—Fe1—C6	68.48 (13)	N4—C11—C10	117.6 (2)
C5—Fe1—C6	164.30 (16)	C11—C12—N3	127.0 (2)
C8—Fe1—C6	67.86 (14)	C11—C12—S1	111.8 (2)
C10—Fe1—C6	41.02 (11)	N3—C12—S1	121.2 (2)
C7—Fe1—C6	40.26 (13)	N1—C13—N3	110.2 (3)
C12—S1—C15	87.53 (14)	N1—C13—H13	124.9
C13—N1—C14	102.3 (3)	N3—C13—H13	124.9
C14—N2—N3	100.1 (3)	N2—C14—N1	116.9 (4)
C13—N3—N2	110.4 (3)	N2—C14—H14	121.5
C13—N3—C12	128.4 (3)	N1—C14—H14	121.5
N2—N3—C12	121.1 (3)	N4—C15—N5	121.3 (3)
C15—N4—C11	111.3 (2)	N4—C15—S1	115.4 (2)
C16—N5—C15	121.4 (3)	N5—C15—S1	123.2 (2)
C5—C1—C2	107.7 (4)	N5—C16—C17	122.5 (3)
C5—C1—Fe1	70.8 (2)	N5—C16—H16	118.8
C2—C1—Fe1	69.9 (2)	C17—C16—H16	118.8
C5—C1—H1	126.1	C22—C17—C18	118.6 (3)
C2—C1—H1	126.1	C22—C17—C16	119.9 (3)
Fe1—C1—H1	124.8	C18—C17—C16	121.5 (3)
C1—C2—C3	106.3 (4)	C19—C18—C17	120.1 (3)
C1—C2—Fe1	69.4 (2)	C19—C18—H18	120.0
C3—C2—Fe1	69.4 (2)	C17—C18—H18	120.0
C1—C2—H2	126.8	C20—C19—C18	120.4 (4)
C3—C2—H2	126.8	C20—C19—H19	119.8
Fe1—C2—H2	125.9	C18—C19—H19	119.8
C4—C3—C2	106.9 (4)	C21—C20—C19	120.0 (3)
C4—C3—Fe1	69.7 (2)	C21—C20—H20	120.0
C2—C3—Fe1	69.5 (2)	C19—C20—H20	120.0
C4—C3—H3	126.6	C20—C21—C22	120.1 (4)
C2—C3—H3	126.6	C20—C21—H21	119.9
Fe1—C3—H3	125.9	C22—C21—H21	119.9
C5—C4—C3	109.7 (4)	C17—C22—C21	120.8 (4)
C5—C4—Fe1	71.2 (2)	C17—C22—H22	119.6
C3—C4—Fe1	70.8 (2)	C21—C22—H22	119.6
C5—C4—H4	125.1
C14—N2—N3—C13	0.5 (4)	C6—Fe1—C7—C8	−119.7 (3)
C14—N2—N3—C12	−176.4 (3)	C4—Fe1—C7—C6	−159.9 (2)
C4—Fe1—C1—C5	−36.2 (3)	C1—Fe1—C7—C6	−38.1 (7)
C3—Fe1—C1—C5	−79.1 (3)	C3—Fe1—C7—C6	−117.6 (3)
C2—Fe1—C1—C5	−118.1 (4)	C2—Fe1—C7—C6	−75.1 (3)
C9—Fe1—C1—C5	81.8 (3)	C9—Fe1—C7—C6	81.9 (2)
C8—Fe1—C1—C5	47.3 (4)	C5—Fe1—C7—C6	165.2 (3)
C10—Fe1—C1—C5	124.9 (3)	C8—Fe1—C7—C6	119.7 (3)
C7—Fe1—C1—C5	−163.7 (6)	C10—Fe1—C7—C6	37.85 (18)
C6—Fe1—C1—C5	165.6 (2)	C6—C7—C8—C9	−0.5 (4)
C4—Fe1—C1—C2	81.9 (3)	Fe1—C7—C8—C9	59.0 (2)
C3—Fe1—C1—C2	39.0 (3)	C6—C7—C8—Fe1	−59.5 (2)
C9—Fe1—C1—C2	−160.1 (3)	C4—Fe1—C8—C7	−117.6 (3)
C5—Fe1—C1—C2	118.1 (4)	C1—Fe1—C8—C7	169.4 (3)
C8—Fe1—C1—C2	165.4 (3)	C3—Fe1—C8—C7	−78.1 (3)
C10—Fe1—C1—C2	−117.0 (3)	C2—Fe1—C8—C7	−50.5 (6)
C7—Fe1—C1—C2	−45.6 (7)	C9—Fe1—C8—C7	119.5 (3)
C6—Fe1—C1—C2	−76.3 (3)	C5—Fe1—C8—C7	−158.5 (2)
C5—C1—C2—C3	1.1 (4)	C10—Fe1—C8—C7	81.6 (2)
Fe1—C1—C2—C3	−59.9 (3)	C6—Fe1—C8—C7	37.31 (19)
C5—C1—C2—Fe1	61.0 (3)	C4—Fe1—C8—C9	122.9 (3)
C4—Fe1—C2—C1	−80.0 (3)	C1—Fe1—C8—C9	49.9 (4)
C3—Fe1—C2—C1	−117.5 (4)	C3—Fe1—C8—C9	162.4 (2)
C9—Fe1—C2—C1	42.6 (4)	C2—Fe1—C8—C9	−170.0 (5)
C5—Fe1—C2—C1	−37.4 (2)	C5—Fe1—C8—C9	81.9 (2)
C8—Fe1—C2—C1	−152.2 (5)	C10—Fe1—C8—C9	−37.91 (18)
C10—Fe1—C2—C1	81.3 (3)	C7—Fe1—C8—C9	−119.5 (3)
C7—Fe1—C2—C1	167.8 (2)	C6—Fe1—C8—C9	−82.2 (2)
C6—Fe1—C2—C1	125.8 (2)	C7—C8—C9—C10	0.3 (3)
C4—Fe1—C2—C3	37.5 (3)	Fe1—C8—C9—C10	59.8 (2)
C1—Fe1—C2—C3	117.5 (4)	C7—C8—C9—Fe1	−59.5 (2)
C9—Fe1—C2—C3	160.1 (3)	C4—Fe1—C9—C10	164.7 (2)
C5—Fe1—C2—C3	80.1 (3)	C1—Fe1—C9—C10	85.2 (2)
C8—Fe1—C2—C3	−34.7 (7)	C3—Fe1—C9—C10	−170.3 (5)
C10—Fe1—C2—C3	−161.1 (3)	C2—Fe1—C9—C10	55.3 (4)
C7—Fe1—C2—C3	−74.7 (3)	C5—Fe1—C9—C10	126.0 (2)
C6—Fe1—C2—C3	−116.6 (3)	C8—Fe1—C9—C10	−119.0 (3)
C1—C2—C3—C4	0.0 (4)	C7—Fe1—C9—C10	−81.81 (19)
Fe1—C2—C3—C4	−59.9 (3)	C6—Fe1—C9—C10	−38.36 (17)
C1—C2—C3—Fe1	59.9 (2)	C4—Fe1—C9—C8	−76.3 (3)
C1—Fe1—C3—C4	79.4 (3)	C1—Fe1—C9—C8	−155.8 (2)
C2—Fe1—C3—C4	118.0 (4)	C3—Fe1—C9—C8	−51.4 (6)
C9—Fe1—C3—C4	−33.1 (7)	C2—Fe1—C9—C8	174.3 (3)
C5—Fe1—C3—C4	36.7 (3)	C5—Fe1—C9—C8	−115.1 (2)
C8—Fe1—C3—C4	−72.4 (3)	C10—Fe1—C9—C8	119.0 (3)
C10—Fe1—C3—C4	163.2 (3)	C7—Fe1—C9—C8	37.1 (2)
C7—Fe1—C3—C4	−114.6 (3)	C6—Fe1—C9—C8	80.6 (2)
C6—Fe1—C3—C4	−157.7 (3)	C8—C9—C10—C6	0.0 (3)
C4—Fe1—C3—C2	−118.0 (4)	Fe1—C9—C10—C6	59.73 (19)
C1—Fe1—C3—C2	−38.5 (2)	C8—C9—C10—C11	−177.7 (3)
C9—Fe1—C3—C2	−151.1 (4)	Fe1—C9—C10—C11	−118.1 (3)
C5—Fe1—C3—C2	−81.2 (3)	C8—C9—C10—Fe1	−59.7 (2)
C8—Fe1—C3—C2	169.6 (2)	C7—C6—C10—C9	−0.4 (3)
C10—Fe1—C3—C2	45.2 (5)	Fe1—C6—C10—C9	−59.41 (19)
C7—Fe1—C3—C2	127.4 (3)	C7—C6—C10—C11	177.6 (3)
C6—Fe1—C3—C2	84.4 (3)	Fe1—C6—C10—C11	118.6 (3)
C2—C3—C4—C5	−1.1 (5)	C7—C6—C10—Fe1	59.1 (2)
Fe1—C3—C4—C5	−60.9 (3)	C4—Fe1—C10—C9	−43.1 (5)
C2—C3—C4—Fe1	59.8 (3)	C1—Fe1—C10—C9	−112.3 (2)
C1—Fe1—C4—C5	36.4 (2)	C3—Fe1—C10—C9	172.3 (4)
C3—Fe1—C4—C5	119.7 (4)	C2—Fe1—C10—C9	−154.8 (2)
C2—Fe1—C4—C5	80.7 (3)	C5—Fe1—C10—C9	−72.7 (2)
C9—Fe1—C4—C5	−72.3 (3)	C8—Fe1—C10—C9	37.95 (18)
C8—Fe1—C4—C5	−114.1 (3)	C7—Fe1—C10—C9	81.3 (2)
C10—Fe1—C4—C5	−39.4 (6)	C6—Fe1—C10—C9	118.4 (2)
C7—Fe1—C4—C5	−155.9 (2)	C4—Fe1—C10—C6	−161.6 (4)
C6—Fe1—C4—C5	171.2 (3)	C1—Fe1—C10—C6	129.3 (2)
C1—Fe1—C4—C3	−83.3 (3)	C3—Fe1—C10—C6	53.8 (4)
C2—Fe1—C4—C3	−39.0 (3)	C2—Fe1—C10—C6	86.8 (2)
C9—Fe1—C4—C3	168.0 (3)	C9—Fe1—C10—C6	−118.4 (2)
C5—Fe1—C4—C3	−119.7 (4)	C5—Fe1—C10—C6	168.9 (2)
C8—Fe1—C4—C3	126.2 (3)	C8—Fe1—C10—C6	−80.5 (2)
C10—Fe1—C4—C3	−159.1 (4)	C7—Fe1—C10—C6	−37.16 (19)
C7—Fe1—C4—C3	84.4 (3)	C4—Fe1—C10—C11	81.4 (5)
C6—Fe1—C4—C3	51.5 (5)	C1—Fe1—C10—C11	12.3 (3)
C3—C4—C5—C1	1.8 (5)	C3—Fe1—C10—C11	−63.2 (5)
Fe1—C4—C5—C1	−58.9 (3)	C2—Fe1—C10—C11	−30.2 (3)
C3—C4—C5—Fe1	60.7 (3)	C9—Fe1—C10—C11	124.6 (3)
C2—C1—C5—C4	−1.8 (4)	C5—Fe1—C10—C11	51.9 (3)
Fe1—C1—C5—C4	58.7 (3)	C8—Fe1—C10—C11	162.5 (3)
C2—C1—C5—Fe1	−60.5 (2)	C7—Fe1—C10—C11	−154.2 (3)
C1—Fe1—C5—C4	−120.7 (4)	C6—Fe1—C10—C11	−117.0 (3)
C3—Fe1—C5—C4	−37.1 (3)	C15—N4—C11—C12	1.9 (3)
C2—Fe1—C5—C4	−82.0 (3)	C15—N4—C11—C10	−177.6 (2)
C9—Fe1—C5—C4	125.1 (3)	C9—C10—C11—C12	5.4 (5)
C8—Fe1—C5—C4	82.6 (3)	C6—C10—C11—C12	−172.0 (3)
C10—Fe1—C5—C4	165.7 (3)	Fe1—C10—C11—C12	−85.1 (3)
C7—Fe1—C5—C4	51.1 (5)	C9—C10—C11—N4	−175.2 (3)
C6—Fe1—C5—C4	−166.6 (5)	C6—C10—C11—N4	7.3 (4)
C4—Fe1—C5—C1	120.7 (4)	Fe1—C10—C11—N4	94.2 (3)
C3—Fe1—C5—C1	83.6 (3)	N4—C11—C12—N3	176.3 (3)
C2—Fe1—C5—C1	38.7 (3)	C10—C11—C12—N3	−4.3 (5)
C9—Fe1—C5—C1	−114.2 (2)	N4—C11—C12—S1	−1.8 (3)
C8—Fe1—C5—C1	−156.6 (2)	C10—C11—C12—S1	177.6 (2)
C10—Fe1—C5—C1	−73.6 (3)	C13—N3—C12—C11	−78.1 (4)
C7—Fe1—C5—C1	171.8 (3)	N2—N3—C12—C11	98.2 (4)
C6—Fe1—C5—C1	−45.9 (6)	C13—N3—C12—S1	99.9 (3)
C4—Fe1—C6—C7	46.2 (5)	N2—N3—C12—S1	−83.9 (3)
C1—Fe1—C6—C7	169.5 (2)	C15—S1—C12—C11	0.9 (2)
C3—Fe1—C6—C7	82.5 (3)	C15—S1—C12—N3	−177.3 (2)
C2—Fe1—C6—C7	126.9 (3)	C14—N1—C13—N3	−0.2 (4)
C9—Fe1—C6—C7	−81.4 (2)	N2—N3—C13—N1	−0.2 (4)
C5—Fe1—C6—C7	−154.8 (5)	C12—N3—C13—N1	176.4 (3)
C8—Fe1—C6—C7	−37.23 (19)	N3—N2—C14—N1	−0.7 (5)
C10—Fe1—C6—C7	−119.6 (3)	C13—N1—C14—N2	0.6 (5)
C4—Fe1—C6—C10	165.7 (4)	C11—N4—C15—N5	−177.2 (2)
C1—Fe1—C6—C10	−70.9 (2)	C11—N4—C15—S1	−1.1 (3)
C3—Fe1—C6—C10	−157.9 (2)	C16—N5—C15—N4	−147.9 (3)
C2—Fe1—C6—C10	−113.5 (2)	C16—N5—C15—S1	36.3 (4)
C9—Fe1—C6—C10	38.17 (16)	C12—S1—C15—N4	0.1 (2)
C5—Fe1—C6—C10	−35.2 (6)	C12—S1—C15—N5	176.2 (3)
C8—Fe1—C6—C10	82.35 (19)	C15—N5—C16—C17	−175.6 (3)
C7—Fe1—C6—C10	119.6 (3)	N5—C16—C17—C22	−176.3 (4)
C10—C6—C7—C8	0.6 (4)	N5—C16—C17—C18	5.6 (5)
Fe1—C6—C7—C8	59.3 (2)	C22—C17—C18—C19	−1.0 (6)
C10—C6—C7—Fe1	−58.8 (2)	C16—C17—C18—C19	177.2 (3)
C4—Fe1—C7—C8	80.4 (3)	C17—C18—C19—C20	−0.1 (6)
C1—Fe1—C7—C8	−157.8 (6)	C18—C19—C20—C21	1.2 (6)
C3—Fe1—C7—C8	122.8 (3)	C19—C20—C21—C22	−1.2 (7)
C2—Fe1—C7—C8	165.2 (2)	C18—C17—C22—C21	1.0 (6)
C9—Fe1—C7—C8	−37.78 (19)	C16—C17—C22—C21	−177.2 (4)
C5—Fe1—C7—C8	45.5 (4)	C20—C21—C22—C17	0.1 (7)
C10—Fe1—C7—C8	−81.8 (2)