[2-(4-Nitro­phenox­yl)-2-(1H-1,2,4-triazol-1-yl)acet­yl]ferrocene

The title compound [Fe(C₅H₅)(C₁₅H₁₁N₄O₄)], has been synthesized as a potent fungicidal agent and its crystal structure was determined. In the crystal structure, there are weak inter­molecular C—H...N inter­actions. The dihedral angles between the plane of the unsubstituted ferrocenyl cyclo­penta­dienyl and thia­zole rings, and between the substituted phenyl and thia­zole rings are 89.3 (3) and 92.3 (2)°, respectively.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.036
• wR factor = 0.088
• Data-to-parameter ratio = 14.5

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature .        293 K
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         N4

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

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 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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Computing details

Data collection: SMART (Bruker, 1998); cell refinement: SMART; data reduction: SAINT (Bruker, 1999); program(s) used to solve structure: SHELX97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1999); software used to prepare material for publication: SHELXTL.

[2-(4-nitrophenoxyl)-2-(1H-1,2,4-triazol-1-yl)acetyl]ferrocene

Crystal data

[Fe(C5H5)(C15H11N4O4)]	Z = 2
Mr = 432.22	F(000) = 444
Triclinic, P1	Dx = 1.528 Mg m^−3
Hall symbol: -p 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.863 (2) Å	Cell parameters from 774 reflections
b = 10.081 (2) Å	θ = 2.3–24.5°
c = 10.731 (3) Å	µ = 0.84 mm^−1
α = 98.839 (6)°	T = 293 K
β = 95.787 (5)°	Parallelepiped, red
γ = 114.928 (7)°	0.26 × 0.22 × 0.18 mm
V = 939.6 (4) Å^3

Data collection

Bruker SMART CCD area-detector diffractometer	3791 independent reflections
Radiation source: fine-focus sealed tube	3026 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.017
φ and ω scans	θmax = 26.4°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→12
Tmin = 0.800, Tmax = 0.860	k = −12→12
5443 measured reflections	l = −13→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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.088	H-atom parameters constrained
S = 1.03	w = 1/[σ^2(Fo^2) + (0.041P)^2 + 0.1868P] where P = (Fo^2 + 2Fc^2)/3
3791 reflections	(Δ/σ)max < 0.001
262 parameters	Δρmax = 0.21 e Å^−3
0 restraints	Δρmin = −0.35 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	0.18107 (4)	0.36718 (4)	0.26123 (3)	0.03664 (12)
N1	0.0548 (2)	0.7682 (2)	0.31880 (18)	0.0406 (4)
N2	−0.0740 (2)	0.6793 (2)	0.2314 (2)	0.0521 (5)
N3	−0.1075 (3)	0.8529 (3)	0.3657 (2)	0.0611 (6)
N4	0.5249 (3)	1.2482 (3)	0.0155 (2)	0.0563 (6)
O1	0.1392 (2)	0.65836 (19)	0.51645 (16)	0.0539 (5)
O2	0.32135 (17)	0.87090 (16)	0.35380 (14)	0.0425 (4)
O3	0.6447 (3)	1.3601 (3)	0.0531 (3)	0.0981 (8)
O4	0.4481 (3)	1.2169 (3)	−0.0900 (2)	0.0814 (7)
C1	0.2770 (2)	0.5593 (2)	0.3985 (2)	0.0368 (5)
C2	0.3719 (3)	0.5650 (3)	0.3047 (2)	0.0440 (6)
H2	0.4008	0.6336	0.2521	0.053*
C3	0.4129 (3)	0.4478 (3)	0.3069 (3)	0.0547 (7)
H3	0.4760	0.4267	0.2568	0.066*
C4	0.3429 (3)	0.3674 (3)	0.3972 (3)	0.0552 (7)
H4	0.3506	0.2835	0.4157	0.066*
C5	0.2596 (3)	0.4348 (3)	0.4548 (2)	0.0461 (6)
H5	0.2031	0.4041	0.5182	0.055*
C6	−0.0309 (3)	0.3328 (3)	0.1807 (2)	0.0512 (7)
H6	−0.0783	0.3928	0.2047	0.061*
C7	0.0628 (3)	0.3502 (3)	0.0877 (2)	0.0527 (6)
H7	0.0887	0.4239	0.0397	0.063*
C8	0.1102 (3)	0.2362 (3)	0.0804 (2)	0.0552 (7)
H8	0.1728	0.2210	0.0264	0.066*
C9	0.0467 (3)	0.1492 (3)	0.1688 (3)	0.0528 (7)
H9	0.0598	0.0665	0.1836	0.063*
C10	−0.0404 (3)	0.2093 (3)	0.2310 (3)	0.0534 (7)
H10	−0.0947	0.1735	0.2943	0.064*
C11	0.1956 (3)	0.6487 (2)	0.4225 (2)	0.0387 (5)
C12	0.1844 (2)	0.7367 (2)	0.3195 (2)	0.0379 (5)
H12	0.1793	0.6806	0.2346	0.046*
C13	0.3640 (2)	0.9572 (2)	0.2632 (2)	0.0362 (5)
C14	0.5023 (3)	1.0832 (3)	0.3027 (2)	0.0434 (6)
H14	0.5586	1.1030	0.3840	0.052*
C15	0.5565 (3)	1.1790 (3)	0.2221 (2)	0.0452 (6)
H15	0.6495	1.2640	0.2475	0.054*
C16	0.4698 (3)	1.1461 (3)	0.1026 (2)	0.0401 (5)
C17	0.3325 (3)	1.0211 (3)	0.0612 (2)	0.0414 (5)
H17	0.2771	1.0013	−0.0205	0.050*
C18	0.2779 (3)	0.9254 (2)	0.1430 (2)	0.0398 (5)
H18	0.1847	0.8408	0.1175	0.048*
C19	0.0316 (3)	0.8690 (3)	0.3979 (3)	0.0541 (7)
H19	0.1037	0.9407	0.4662	0.065*
C20	−0.1661 (3)	0.7363 (3)	0.2646 (3)	0.0575 (7)
H20	−0.2656	0.6983	0.2209	0.069*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Fe1	0.03421 (19)	0.03897 (19)	0.03424 (19)	0.01614 (14)	0.00341 (13)	0.00326 (13)
N1	0.0389 (11)	0.0386 (10)	0.0405 (11)	0.0150 (9)	0.0058 (9)	0.0056 (9)
N2	0.0417 (12)	0.0599 (13)	0.0455 (12)	0.0172 (11)	−0.0007 (10)	0.0075 (10)
N3	0.0600 (15)	0.0646 (15)	0.0721 (17)	0.0377 (13)	0.0178 (13)	0.0186 (13)
N4	0.0485 (14)	0.0629 (15)	0.0638 (16)	0.0237 (12)	0.0182 (12)	0.0297 (12)
O1	0.0718 (13)	0.0561 (11)	0.0407 (10)	0.0315 (10)	0.0242 (9)	0.0121 (8)
O2	0.0395 (9)	0.0362 (8)	0.0393 (9)	0.0066 (7)	0.0009 (7)	0.0082 (7)
O3	0.0748 (16)	0.0817 (16)	0.1042 (19)	−0.0066 (13)	0.0095 (14)	0.0547 (15)
O4	0.0764 (15)	0.0972 (17)	0.0682 (15)	0.0269 (13)	0.0131 (12)	0.0460 (13)
C1	0.0347 (12)	0.0352 (12)	0.0318 (12)	0.0096 (10)	0.0012 (9)	0.0038 (9)
C2	0.0336 (13)	0.0453 (13)	0.0468 (14)	0.0118 (11)	0.0082 (10)	0.0092 (11)
C3	0.0369 (14)	0.0628 (17)	0.0637 (18)	0.0262 (13)	0.0039 (12)	0.0030 (14)
C4	0.0538 (17)	0.0478 (15)	0.0624 (17)	0.0274 (13)	−0.0098 (13)	0.0061 (13)
C5	0.0533 (15)	0.0443 (13)	0.0329 (12)	0.0168 (12)	−0.0032 (11)	0.0088 (10)
C6	0.0372 (14)	0.0528 (15)	0.0541 (16)	0.0225 (12)	−0.0079 (11)	−0.0111 (12)
C7	0.0522 (16)	0.0578 (16)	0.0413 (14)	0.0223 (13)	−0.0048 (12)	0.0069 (12)
C8	0.0575 (17)	0.0668 (17)	0.0380 (14)	0.0317 (14)	0.0040 (12)	−0.0071 (13)
C9	0.0569 (17)	0.0405 (14)	0.0528 (16)	0.0214 (12)	−0.0030 (13)	−0.0032 (12)
C10	0.0402 (14)	0.0493 (15)	0.0529 (16)	0.0079 (12)	0.0066 (12)	−0.0012 (12)
C11	0.0387 (13)	0.0310 (11)	0.0344 (12)	0.0068 (10)	0.0040 (10)	0.0013 (9)
C12	0.0376 (13)	0.0317 (11)	0.0367 (12)	0.0100 (10)	0.0045 (10)	0.0035 (9)
C13	0.0338 (12)	0.0343 (12)	0.0415 (13)	0.0158 (10)	0.0080 (10)	0.0085 (10)
C14	0.0361 (13)	0.0422 (13)	0.0429 (14)	0.0114 (11)	−0.0009 (10)	0.0072 (11)
C15	0.0326 (13)	0.0408 (13)	0.0571 (16)	0.0110 (10)	0.0071 (11)	0.0127 (11)
C16	0.0376 (13)	0.0426 (13)	0.0477 (14)	0.0208 (11)	0.0166 (11)	0.0161 (11)
C17	0.0410 (13)	0.0476 (13)	0.0371 (13)	0.0216 (11)	0.0057 (10)	0.0086 (10)
C18	0.0340 (12)	0.0338 (12)	0.0433 (13)	0.0091 (10)	0.0032 (10)	0.0052 (10)
C19	0.0595 (18)	0.0476 (15)	0.0564 (17)	0.0269 (13)	0.0110 (13)	0.0051 (12)
C20	0.0433 (15)	0.0724 (19)	0.0601 (18)	0.0249 (14)	0.0076 (13)	0.0274 (15)

Geometric parameters (Å, º)

Fe1—C2	2.027 (2)	C3—H3	0.9300
Fe1—C1	2.028 (2)	C4—C5	1.400 (4)
Fe1—C7	2.038 (3)	C4—H4	0.9300
Fe1—C8	2.040 (2)	C5—H5	0.9300
Fe1—C6	2.042 (2)	C6—C10	1.403 (4)
Fe1—C5	2.043 (2)	C6—C7	1.409 (4)
Fe1—C10	2.044 (3)	C6—H6	0.9300
Fe1—C9	2.045 (2)	C7—C8	1.406 (4)
Fe1—C4	2.050 (3)	C7—H7	0.9300
Fe1—C3	2.052 (3)	C8—C9	1.406 (4)
N1—C19	1.333 (3)	C8—H8	0.9300
N1—N2	1.356 (3)	C9—C10	1.407 (4)
N1—C12	1.441 (3)	C9—H9	0.9300
N2—C20	1.313 (3)	C10—H10	0.9300
N3—C19	1.314 (3)	C11—C12	1.543 (3)
N3—C20	1.342 (4)	C12—H12	0.9800
N4—O4	1.213 (3)	C13—C18	1.382 (3)
N4—O3	1.213 (3)	C13—C14	1.382 (3)
N4—C16	1.468 (3)	C14—C15	1.372 (3)
O1—C11	1.211 (3)	C14—H14	0.9300
O2—C13	1.383 (3)	C15—C16	1.377 (3)
O2—C12	1.413 (3)	C15—H15	0.9300
C1—C5	1.429 (3)	C16—C17	1.373 (3)
C1—C2	1.434 (3)	C17—C18	1.381 (3)
C1—C11	1.450 (3)	C17—H17	0.9300
C2—C3	1.403 (3)	C18—H18	0.9300
C2—H2	0.9300	C19—H19	0.9300
C3—C4	1.406 (4)	C20—H20	0.9300
C2—Fe1—C1	41.41 (9)	C3—C4—Fe1	70.05 (15)
C2—Fe1—C7	108.28 (11)	C5—C4—H4	125.6
C1—Fe1—C7	122.39 (10)	C3—C4—H4	125.6
C2—Fe1—C8	120.97 (11)	Fe1—C4—H4	126.2
C1—Fe1—C8	157.26 (10)	C4—C5—C1	107.7 (2)
C7—Fe1—C8	40.35 (10)	C4—C5—Fe1	70.25 (15)
C2—Fe1—C6	126.18 (10)	C1—C5—Fe1	68.90 (12)
C1—Fe1—C6	109.00 (9)	C4—C5—H5	126.2
C7—Fe1—C6	40.41 (10)	C1—C5—H5	126.2
C8—Fe1—C6	67.69 (10)	Fe1—C5—H5	126.2
C2—Fe1—C5	69.10 (10)	C10—C6—C7	108.2 (2)
C1—Fe1—C5	41.08 (9)	C10—C6—Fe1	69.98 (14)
C7—Fe1—C5	157.90 (10)	C7—C6—Fe1	69.64 (14)
C8—Fe1—C5	160.11 (10)	C10—C6—H6	125.9
C6—Fe1—C5	122.30 (10)	C7—C6—H6	125.9
C2—Fe1—C10	162.87 (10)	Fe1—C6—H6	126.1
C1—Fe1—C10	125.32 (10)	C8—C7—C6	107.7 (2)
C7—Fe1—C10	67.84 (11)	C8—C7—Fe1	69.87 (14)
C8—Fe1—C10	67.70 (11)	C6—C7—Fe1	69.95 (14)
C6—Fe1—C10	40.17 (10)	C8—C7—H7	126.2
C5—Fe1—C10	107.83 (11)	C6—C7—H7	126.2
C2—Fe1—C9	155.47 (10)	Fe1—C7—H7	125.6
C1—Fe1—C9	161.35 (10)	C9—C8—C7	108.2 (2)
C7—Fe1—C9	67.83 (11)	C9—C8—Fe1	70.06 (14)
C8—Fe1—C9	40.26 (11)	C7—C8—Fe1	69.78 (14)
C6—Fe1—C9	67.61 (10)	C9—C8—H8	125.9
C5—Fe1—C9	123.84 (11)	C7—C8—H8	125.9
C10—Fe1—C9	40.27 (10)	Fe1—C8—H8	125.9
C2—Fe1—C4	68.16 (11)	C8—C9—C10	107.9 (2)
C1—Fe1—C4	68.10 (10)	C8—C9—Fe1	69.68 (15)
C7—Fe1—C4	161.10 (11)	C10—C9—Fe1	69.84 (14)
C8—Fe1—C4	124.21 (11)	C8—C9—H9	126.0
C6—Fe1—C4	156.47 (12)	C10—C9—H9	126.0
C5—Fe1—C4	40.01 (10)	Fe1—C9—H9	126.0
C10—Fe1—C4	121.04 (12)	C6—C10—C9	108.0 (2)
C9—Fe1—C4	107.23 (11)	C6—C10—Fe1	69.86 (14)
C2—Fe1—C3	40.23 (10)	C9—C10—Fe1	69.89 (15)
C1—Fe1—C3	68.10 (10)	C6—C10—H10	126.0
C7—Fe1—C3	125.35 (11)	C9—C10—H10	126.0
C8—Fe1—C3	107.89 (11)	Fe1—C10—H10	125.8
C6—Fe1—C3	162.52 (11)	O1—C11—C1	124.4 (2)
C5—Fe1—C3	67.69 (11)	O1—C11—C12	119.7 (2)
C10—Fe1—C3	155.64 (11)	C1—C11—C12	115.93 (19)
C9—Fe1—C3	120.78 (11)	O2—C12—N1	110.72 (17)
C4—Fe1—C3	40.10 (11)	O2—C12—C11	104.24 (17)
C19—N1—N2	109.6 (2)	N1—C12—C11	112.10 (18)
C19—N1—C12	130.9 (2)	O2—C12—H12	109.9
N2—N1—C12	119.34 (19)	N1—C12—H12	109.9
C20—N2—N1	101.7 (2)	C11—C12—H12	109.9
C19—N3—C20	102.4 (2)	C18—C13—C14	121.1 (2)
O4—N4—O3	123.4 (2)	C18—C13—O2	124.5 (2)
O4—N4—C16	118.4 (2)	C14—C13—O2	114.4 (2)
O3—N4—C16	118.2 (2)	C15—C14—C13	120.1 (2)
C13—O2—C12	118.13 (17)	C15—C14—H14	120.0
C5—C1—C2	107.5 (2)	C13—C14—H14	120.0
C5—C1—C11	124.7 (2)	C14—C15—C16	118.3 (2)
C2—C1—C11	127.4 (2)	C14—C15—H15	120.9
C5—C1—Fe1	70.02 (13)	C16—C15—H15	120.9
C2—C1—Fe1	69.25 (13)	C17—C16—C15	122.6 (2)
C11—C1—Fe1	120.08 (15)	C17—C16—N4	118.3 (2)
C3—C2—C1	107.3 (2)	C15—C16—N4	119.1 (2)
C3—C2—Fe1	70.86 (15)	C16—C17—C18	118.9 (2)
C1—C2—Fe1	69.34 (13)	C16—C17—H17	120.5
C3—C2—H2	126.4	C18—C17—H17	120.5
C1—C2—H2	126.4	C17—C18—C13	119.1 (2)
Fe1—C2—H2	125.0	C17—C18—H18	120.5
C2—C3—C4	108.8 (2)	C13—C18—H18	120.5
C2—C3—Fe1	68.91 (14)	N3—C19—N1	110.5 (2)
C4—C3—Fe1	69.85 (15)	N3—C19—H19	124.8
C2—C3—H3	125.6	N1—C19—H19	124.8
C4—C3—H3	125.6	N2—C20—N3	115.8 (2)
Fe1—C3—H3	127.2	N2—C20—H20	122.1
C5—C4—C3	108.7 (2)	N3—C20—H20	122.1
C5—C4—Fe1	69.73 (14)
C19—N1—N2—C20	0.8 (3)	C5—Fe1—C6—C7	161.49 (14)
C12—N1—N2—C20	176.7 (2)	C10—Fe1—C6—C7	−119.3 (2)
C2—Fe1—C1—C5	−118.7 (2)	C9—Fe1—C6—C7	−81.62 (17)
C7—Fe1—C1—C5	160.39 (15)	C4—Fe1—C6—C7	−163.4 (2)
C8—Fe1—C1—C5	−164.8 (2)	C3—Fe1—C6—C7	40.7 (4)
C6—Fe1—C1—C5	117.71 (16)	C10—C6—C7—C8	0.4 (3)
C10—Fe1—C1—C5	76.01 (18)	Fe1—C6—C7—C8	59.95 (17)
C9—Fe1—C1—C5	41.6 (4)	C10—C6—C7—Fe1	−59.58 (17)
C4—Fe1—C1—C5	−37.33 (15)	C2—Fe1—C7—C8	116.62 (17)
C3—Fe1—C1—C5	−80.70 (16)	C1—Fe1—C7—C8	160.08 (16)
C7—Fe1—C1—C2	−80.93 (17)	C6—Fe1—C7—C8	−118.6 (2)
C8—Fe1—C1—C2	−46.1 (3)	C5—Fe1—C7—C8	−164.0 (2)
C6—Fe1—C1—C2	−123.60 (15)	C10—Fe1—C7—C8	−81.17 (18)
C5—Fe1—C1—C2	118.7 (2)	C9—Fe1—C7—C8	−37.53 (16)
C10—Fe1—C1—C2	−165.31 (15)	C4—Fe1—C7—C8	40.8 (4)
C9—Fe1—C1—C2	160.2 (3)	C3—Fe1—C7—C8	75.3 (2)
C4—Fe1—C1—C2	81.35 (16)	C2—Fe1—C7—C6	−124.82 (15)
C3—Fe1—C1—C2	37.98 (15)	C1—Fe1—C7—C6	−81.35 (17)
C2—Fe1—C1—C11	122.1 (2)	C8—Fe1—C7—C6	118.6 (2)
C7—Fe1—C1—C11	41.1 (2)	C5—Fe1—C7—C6	−45.5 (3)
C8—Fe1—C1—C11	75.9 (3)	C10—Fe1—C7—C6	37.39 (15)
C6—Fe1—C1—C11	−1.5 (2)	C9—Fe1—C7—C6	81.04 (17)
C5—Fe1—C1—C11	−119.2 (2)	C4—Fe1—C7—C6	159.3 (3)
C10—Fe1—C1—C11	−43.2 (2)	C3—Fe1—C7—C6	−166.10 (15)
C9—Fe1—C1—C11	−77.7 (4)	C6—C7—C8—C9	−0.3 (3)
C4—Fe1—C1—C11	−156.6 (2)	Fe1—C7—C8—C9	59.74 (18)
C3—Fe1—C1—C11	160.1 (2)	C6—C7—C8—Fe1	−59.99 (17)
C5—C1—C2—C3	−1.2 (3)	C2—Fe1—C8—C9	158.91 (15)
C11—C1—C2—C3	−173.7 (2)	C1—Fe1—C8—C9	−167.3 (2)
Fe1—C1—C2—C3	−61.02 (17)	C7—Fe1—C8—C9	−119.2 (2)
C5—C1—C2—Fe1	59.82 (15)	C6—Fe1—C8—C9	−81.23 (17)
C11—C1—C2—Fe1	−112.6 (2)	C5—Fe1—C8—C9	43.1 (4)
C1—Fe1—C2—C3	117.9 (2)	C10—Fe1—C8—C9	−37.66 (16)
C7—Fe1—C2—C3	−123.56 (17)	C4—Fe1—C8—C9	75.6 (2)
C8—Fe1—C2—C3	−81.11 (18)	C3—Fe1—C8—C9	116.80 (17)
C6—Fe1—C2—C3	−164.82 (16)	C2—Fe1—C8—C7	−81.88 (19)
C5—Fe1—C2—C3	79.75 (17)	C1—Fe1—C8—C7	−48.1 (3)
C10—Fe1—C2—C3	162.5 (3)	C6—Fe1—C8—C7	37.99 (16)
C9—Fe1—C2—C3	−47.0 (3)	C5—Fe1—C8—C7	162.3 (3)
C4—Fe1—C2—C3	36.66 (16)	C10—Fe1—C8—C7	81.56 (18)
C7—Fe1—C2—C1	118.58 (14)	C9—Fe1—C8—C7	119.2 (2)
C8—Fe1—C2—C1	161.04 (14)	C4—Fe1—C8—C7	−165.18 (16)
C6—Fe1—C2—C1	77.32 (17)	C3—Fe1—C8—C7	−123.99 (17)
C5—Fe1—C2—C1	−38.10 (14)	C7—C8—C9—C10	0.0 (3)
C10—Fe1—C2—C1	44.6 (4)	Fe1—C8—C9—C10	59.61 (18)
C9—Fe1—C2—C1	−164.9 (2)	C7—C8—C9—Fe1	−59.57 (18)
C4—Fe1—C2—C1	−81.20 (15)	C2—Fe1—C9—C8	−48.0 (3)
C3—Fe1—C2—C1	−117.9 (2)	C1—Fe1—C9—C8	164.6 (3)
C1—C2—C3—C4	1.5 (3)	C7—Fe1—C9—C8	37.60 (16)
Fe1—C2—C3—C4	−58.58 (18)	C6—Fe1—C9—C8	81.44 (17)
C1—C2—C3—Fe1	60.05 (16)	C5—Fe1—C9—C8	−163.75 (15)
C1—Fe1—C3—C2	−39.07 (14)	C10—Fe1—C9—C8	119.0 (2)
C7—Fe1—C3—C2	75.94 (18)	C4—Fe1—C9—C8	−123.00 (17)
C8—Fe1—C3—C2	117.10 (16)	C3—Fe1—C9—C8	−81.37 (19)
C6—Fe1—C3—C2	44.7 (4)	C2—Fe1—C9—C10	−167.0 (2)
C5—Fe1—C3—C2	−83.57 (16)	C1—Fe1—C9—C10	45.6 (4)
C10—Fe1—C3—C2	−167.6 (2)	C7—Fe1—C9—C10	−81.42 (17)
C9—Fe1—C3—C2	159.28 (15)	C8—Fe1—C9—C10	−119.0 (2)
C4—Fe1—C3—C2	−120.6 (2)	C6—Fe1—C9—C10	−37.59 (16)
C2—Fe1—C3—C4	120.6 (2)	C5—Fe1—C9—C10	77.22 (19)
C1—Fe1—C3—C4	81.57 (16)	C4—Fe1—C9—C10	117.97 (17)
C7—Fe1—C3—C4	−163.42 (15)	C3—Fe1—C9—C10	159.60 (16)
C8—Fe1—C3—C4	−122.26 (16)	C7—C6—C10—C9	−0.3 (3)
C6—Fe1—C3—C4	165.4 (3)	Fe1—C6—C10—C9	−59.71 (18)
C5—Fe1—C3—C4	37.07 (15)	C7—C6—C10—Fe1	59.37 (17)
C10—Fe1—C3—C4	−47.0 (3)	C8—C9—C10—C6	0.2 (3)
C9—Fe1—C3—C4	−80.08 (18)	Fe1—C9—C10—C6	59.69 (17)
C2—C3—C4—C5	−1.2 (3)	C8—C9—C10—Fe1	−59.51 (18)
Fe1—C3—C4—C5	−59.20 (18)	C2—Fe1—C10—C6	42.5 (4)
C2—C3—C4—Fe1	58.00 (18)	C1—Fe1—C10—C6	77.24 (18)
C2—Fe1—C4—C5	83.09 (16)	C7—Fe1—C10—C6	−37.62 (15)
C1—Fe1—C4—C5	38.30 (14)	C8—Fe1—C10—C6	−81.37 (17)
C7—Fe1—C4—C5	165.8 (3)	C5—Fe1—C10—C6	119.29 (15)
C8—Fe1—C4—C5	−163.47 (15)	C9—Fe1—C10—C6	−119.0 (2)
C6—Fe1—C4—C5	−49.2 (3)	C4—Fe1—C10—C6	161.10 (15)
C10—Fe1—C4—C5	−80.74 (18)	C3—Fe1—C10—C6	−165.6 (2)
C9—Fe1—C4—C5	−122.52 (16)	C2—Fe1—C10—C9	161.5 (3)
C3—Fe1—C4—C5	119.9 (2)	C1—Fe1—C10—C9	−163.75 (15)
C2—Fe1—C4—C3	−36.78 (15)	C7—Fe1—C10—C9	81.40 (17)
C1—Fe1—C4—C3	−81.56 (16)	C8—Fe1—C10—C9	37.65 (16)
C7—Fe1—C4—C3	45.9 (4)	C6—Fe1—C10—C9	119.0 (2)
C8—Fe1—C4—C3	76.67 (19)	C5—Fe1—C10—C9	−121.69 (16)
C6—Fe1—C4—C3	−169.0 (2)	C4—Fe1—C10—C9	−79.89 (19)
C5—Fe1—C4—C3	−119.9 (2)	C3—Fe1—C10—C9	−46.6 (3)
C10—Fe1—C4—C3	159.40 (15)	C5—C1—C11—O1	22.3 (4)
C9—Fe1—C4—C3	117.62 (16)	C2—C1—C11—O1	−166.5 (2)
C3—C4—C5—C1	0.4 (3)	Fe1—C1—C11—O1	107.7 (2)
Fe1—C4—C5—C1	−58.97 (16)	C5—C1—C11—C12	−158.4 (2)
C3—C4—C5—Fe1	59.40 (18)	C2—C1—C11—C12	12.9 (3)
C2—C1—C5—C4	0.5 (3)	Fe1—C1—C11—C12	−73.0 (2)
C11—C1—C5—C4	173.2 (2)	C13—O2—C12—N1	−75.4 (2)
Fe1—C1—C5—C4	59.82 (17)	C13—O2—C12—C11	163.84 (17)
C2—C1—C5—Fe1	−59.34 (15)	C19—N1—C12—O2	−39.7 (3)
C11—C1—C5—Fe1	113.4 (2)	N2—N1—C12—O2	145.4 (2)
C2—Fe1—C5—C4	−80.54 (17)	C19—N1—C12—C11	76.3 (3)
C1—Fe1—C5—C4	−118.9 (2)	N2—N1—C12—C11	−98.6 (2)
C7—Fe1—C5—C4	−167.8 (3)	O1—C11—C12—O2	94.4 (2)
C8—Fe1—C5—C4	43.8 (4)	C1—C11—C12—O2	−85.0 (2)
C6—Fe1—C5—C4	159.06 (16)	O1—C11—C12—N1	−25.4 (3)
C10—Fe1—C5—C4	117.33 (17)	C1—C11—C12—N1	155.21 (19)
C9—Fe1—C5—C4	75.87 (19)	C12—O2—C13—C18	3.5 (3)
C3—Fe1—C5—C4	−37.14 (16)	C12—O2—C13—C14	−177.45 (19)
C2—Fe1—C5—C1	38.40 (14)	C18—C13—C14—C15	−0.2 (4)
C7—Fe1—C5—C1	−48.9 (3)	O2—C13—C14—C15	−179.3 (2)
C8—Fe1—C5—C1	162.7 (3)	C13—C14—C15—C16	0.2 (4)
C6—Fe1—C5—C1	−82.01 (17)	C14—C15—C16—C17	−0.5 (4)
C10—Fe1—C5—C1	−123.73 (15)	C14—C15—C16—N4	179.2 (2)
C9—Fe1—C5—C1	−165.20 (14)	O4—N4—C16—C17	−1.1 (3)
C4—Fe1—C5—C1	118.9 (2)	O3—N4—C16—C17	178.5 (3)
C3—Fe1—C5—C1	81.79 (15)	O4—N4—C16—C15	179.1 (2)
C2—Fe1—C6—C10	−165.73 (14)	O3—N4—C16—C15	−1.2 (4)
C1—Fe1—C6—C10	−122.69 (15)	C15—C16—C17—C18	0.9 (3)
C7—Fe1—C6—C10	119.3 (2)	N4—C16—C17—C18	−178.9 (2)
C8—Fe1—C6—C10	81.38 (17)	C16—C17—C18—C13	−0.8 (3)
C5—Fe1—C6—C10	−79.20 (17)	C14—C13—C18—C17	0.5 (3)
C9—Fe1—C6—C10	37.69 (15)	O2—C13—C18—C17	179.5 (2)
C4—Fe1—C6—C10	−44.1 (3)	C20—N3—C19—N1	0.7 (3)
C3—Fe1—C6—C10	160.0 (3)	N2—N1—C19—N3	−1.0 (3)
C2—Fe1—C6—C7	74.97 (18)	C12—N1—C19—N3	−176.3 (2)
C1—Fe1—C6—C7	118.00 (15)	N1—N2—C20—N3	−0.3 (3)
C8—Fe1—C6—C7	−37.93 (16)	C19—N3—C20—N2	−0.2 (3)