Bis­[1-ferrocenyl-3-(2,6-di­methyl­phenyl)­amino­but-2-en-1-onato]nickel(II)

In the title compound, [Ni(C₂₂H₂₂FeNO)₂], the Ni^II ion lies on an inversion center and has a square planar coordination geometry formed by bidentate en­amino­ne ligands. The Ni-N and Ni-O bond distances are 1.928 (2) and 1.850 (2) Å, respectively.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.033
• wR factor = 0.091
• Data-to-parameter ratio = 15.7

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        Fe1
PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety        C22

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   2 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
   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
   1 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, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Bis[1-ferrocenyl-3-(2,6-dimethylphenyl)aminobut-2-en-1-onato]nickel(II)

Crystal data

[Ni(C22H22FeNO)2]	Z = 1
Mr = 803.22	F(000) = 418
Triclinic, P1	Dx = 1.439 Mg m^−3
Hall symbol: -P 1	Melting point = 485–486 K
a = 7.165 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.709 (3) Å	Cell parameters from 931 reflections
c = 13.999 (5) Å	θ = 3.3–26.1°
α = 92.878 (5)°	µ = 1.32 mm^−1
β = 102.008 (4)°	T = 293 K
γ = 102.174 (5)°	Block, orange-yellow
V = 926.6 (5) Å^3	0.20 × 0.16 × 0.12 mm

Data collection

Bruker SMART 1000 CCD area-detector diffractometer	3750 independent reflections
Radiation source: fine-focus sealed tube	2983 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.019
φ and ω scans	θmax = 26.3°, θmin = 1.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −8→7
Tmin = 0.802, Tmax = 0.846	k = −12→9
5299 measured reflections	l = −17→16

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)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.091	H-atom parameters constrained
S = 1.08	w = 1/[σ^2(Fo^2) + (0.0431P)^2 + 0.3411P] where P = (Fo^2 + 2Fc^2)/3
3697 reflections	(Δ/σ)max = 0.001
235 parameters	Δρmax = 0.35 e Å^−3
0 restraints	Δρmin = −0.25 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
Ni1	0.5000	0.5000	0.5000	0.02568 (13)
Fe1	0.45459 (5)	0.25589 (4)	0.84336 (3)	0.02995 (12)
O1	0.5514 (3)	0.45401 (19)	0.62804 (12)	0.0342 (4)
N1	0.5751 (3)	0.3367 (2)	0.44913 (15)	0.0290 (5)
C1	0.2018 (5)	0.1871 (4)	0.7409 (3)	0.0594 (10)
H1	0.1830	0.2000	0.6708	0.071*
C2	0.1745 (4)	0.2808 (4)	0.8143 (3)	0.0573 (9)
H2	0.1339	0.3703	0.8042	0.069*
C3	0.2142 (4)	0.2232 (4)	0.9041 (3)	0.0518 (8)
H3	0.2079	0.2661	0.9680	0.062*
C4	0.2679 (5)	0.0931 (3)	0.8869 (2)	0.0489 (8)
H4	0.3051	0.0304	0.9366	0.059*
C5	0.2608 (5)	0.0709 (4)	0.7859 (2)	0.0523 (8)
H5	0.2902	−0.0106	0.7527	0.063*
C6	0.6328 (4)	0.4486 (3)	0.83872 (19)	0.0356 (6)
H6	0.5893	0.5357	0.8233	0.043*
C7	0.6788 (4)	0.4030 (3)	0.9336 (2)	0.0422 (7)
H7	0.6720	0.4528	0.9950	0.051*
C8	0.7328 (4)	0.2713 (3)	0.9241 (2)	0.0406 (7)
H8	0.7702	0.2146	0.9778	0.049*
C9	0.7201 (4)	0.2348 (3)	0.8237 (2)	0.0352 (6)
H9	0.7491	0.1492	0.7958	0.042*
C10	0.6591 (4)	0.3460 (3)	0.76944 (18)	0.0305 (5)
C11	0.6249 (3)	0.3516 (3)	0.66210 (18)	0.0277 (5)
C12	0.6746 (4)	0.2513 (3)	0.60579 (19)	0.0360 (6)
H12	0.7292	0.1827	0.6379	0.043*
C13	0.6494 (4)	0.2445 (3)	0.50383 (19)	0.0332 (6)
C14	0.7111 (5)	0.1216 (3)	0.4565 (2)	0.0495 (8)
H14A	0.5982	0.0597	0.4146	0.074*
H14B	0.7697	0.0701	0.5067	0.074*
H14C	0.8043	0.1576	0.4184	0.074*
C15	0.5545 (4)	0.3063 (3)	0.34495 (18)	0.0299 (5)
C16	0.7140 (4)	0.3557 (3)	0.30300 (19)	0.0348 (6)
C17	0.6978 (5)	0.3125 (3)	0.2046 (2)	0.0451 (7)
H17	0.8032	0.3428	0.1757	0.054*
C18	0.5283 (5)	0.2259 (3)	0.1494 (2)	0.0519 (8)
H18	0.5206	0.1970	0.0840	0.062*
C19	0.3705 (5)	0.1820 (3)	0.1905 (2)	0.0486 (8)
H19	0.2558	0.1250	0.1522	0.058*
C20	0.3794 (4)	0.2215 (3)	0.2892 (2)	0.0381 (6)
C21	0.2065 (5)	0.1720 (4)	0.3334 (3)	0.0571 (9)
H21A	0.0912	0.1386	0.2820	0.086*
H21B	0.1887	0.2492	0.3736	0.086*
H21C	0.2287	0.0965	0.3729	0.086*
C22	0.8968 (4)	0.4517 (3)	0.3624 (2)	0.0469 (7)
H22A	0.9902	0.4748	0.3222	0.070*
H22B	0.9511	0.4050	0.4168	0.070*
H22C	0.8667	0.5369	0.3865	0.070*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Ni1	0.0327 (3)	0.0256 (2)	0.0211 (2)	0.00856 (18)	0.00862 (18)	0.00459 (17)
Fe1	0.0302 (2)	0.0343 (2)	0.0265 (2)	0.00730 (16)	0.00796 (15)	0.00672 (16)
O1	0.0491 (11)	0.0351 (10)	0.0238 (9)	0.0183 (9)	0.0101 (8)	0.0062 (8)
N1	0.0377 (12)	0.0278 (11)	0.0233 (11)	0.0086 (9)	0.0100 (9)	0.0024 (9)
C1	0.0360 (17)	0.082 (3)	0.0479 (19)	−0.0041 (17)	−0.0040 (14)	0.0169 (18)
C2	0.0321 (16)	0.063 (2)	0.081 (3)	0.0156 (15)	0.0130 (16)	0.028 (2)
C3	0.0413 (17)	0.063 (2)	0.059 (2)	0.0102 (15)	0.0268 (15)	0.0125 (17)
C4	0.0462 (18)	0.0456 (18)	0.0531 (19)	−0.0009 (14)	0.0163 (15)	0.0135 (15)
C5	0.0477 (18)	0.0469 (18)	0.052 (2)	−0.0060 (15)	0.0065 (15)	−0.0026 (15)
C6	0.0412 (15)	0.0326 (14)	0.0309 (14)	0.0038 (12)	0.0083 (12)	0.0034 (11)
C7	0.0470 (17)	0.0483 (17)	0.0255 (14)	0.0017 (14)	0.0050 (12)	0.0013 (12)
C8	0.0349 (15)	0.0573 (19)	0.0312 (14)	0.0129 (13)	0.0052 (12)	0.0166 (13)
C9	0.0330 (14)	0.0455 (16)	0.0337 (14)	0.0163 (12)	0.0124 (11)	0.0136 (12)
C10	0.0288 (13)	0.0352 (14)	0.0278 (13)	0.0066 (11)	0.0070 (10)	0.0064 (11)
C11	0.0286 (13)	0.0300 (13)	0.0264 (13)	0.0060 (10)	0.0097 (10)	0.0076 (10)
C12	0.0493 (17)	0.0342 (14)	0.0303 (14)	0.0174 (12)	0.0121 (12)	0.0104 (11)
C13	0.0422 (15)	0.0286 (13)	0.0331 (14)	0.0115 (11)	0.0142 (12)	0.0044 (11)
C14	0.081 (2)	0.0413 (17)	0.0382 (16)	0.0313 (16)	0.0225 (16)	0.0076 (13)
C15	0.0414 (15)	0.0255 (12)	0.0248 (12)	0.0108 (11)	0.0084 (11)	0.0025 (10)
C16	0.0440 (16)	0.0342 (14)	0.0297 (14)	0.0133 (12)	0.0111 (12)	0.0058 (11)
C17	0.062 (2)	0.0499 (18)	0.0346 (16)	0.0232 (16)	0.0228 (14)	0.0096 (14)
C18	0.081 (3)	0.0480 (19)	0.0292 (16)	0.0257 (18)	0.0093 (16)	−0.0023 (14)
C19	0.066 (2)	0.0323 (15)	0.0368 (16)	0.0081 (14)	−0.0073 (15)	−0.0056 (13)
C20	0.0453 (16)	0.0278 (13)	0.0383 (15)	0.0073 (12)	0.0038 (12)	0.0044 (12)
C21	0.0466 (19)	0.0512 (19)	0.066 (2)	−0.0022 (15)	0.0099 (16)	0.0046 (17)
C22	0.0438 (17)	0.0502 (18)	0.0479 (18)	0.0075 (14)	0.0149 (14)	0.0086 (15)

Geometric parameters (Å, º)

Ni1—N1	1.928 (2)	C7—H7	0.9800
Ni1—N1^i	1.928 (2)	C8—C9	1.411 (4)
Ni1—O1	1.850 (2)	C8—H8	0.9800
Ni1—O1^i	1.850 (2)	C9—C10	1.441 (4)
Fe1—C1	2.024 (3)	C9—H9	0.9800
Fe1—C9	2.028 (3)	C10—C11	1.477 (3)
Fe1—C2	2.032 (3)	C11—C12	1.372 (4)
Fe1—C5	2.035 (3)	C12—C13	1.397 (4)
Fe1—C10	2.040 (3)	C12—H12	0.9300
Fe1—C6	2.043 (3)	C13—C14	1.524 (4)
Fe1—C8	2.048 (3)	C14—H14A	0.9600
Fe1—C3	2.049 (3)	C14—H14B	0.9600
Fe1—C4	2.050 (3)	C14—H14C	0.9600
Fe1—C7	2.056 (3)	C15—C20	1.398 (4)
O1—C11	1.287 (3)	C15—C16	1.399 (4)
N1—C13	1.331 (3)	C16—C17	1.394 (4)
N1—C15	1.444 (3)	C16—C22	1.494 (4)
C1—C2	1.409 (5)	C17—C18	1.376 (4)
C1—C5	1.419 (5)	C17—H17	0.9300
C1—H1	0.9800	C18—C19	1.372 (5)
C2—C3	1.402 (5)	C18—H18	0.9300
C2—H2	0.9800	C19—C20	1.401 (4)
C3—C4	1.420 (5)	C19—H19	0.9300
C3—H3	0.9800	C20—C21	1.498 (4)
C4—C5	1.408 (5)	C21—H21A	0.9600
C4—H4	0.9800	C21—H21B	0.9600
C5—H5	0.9800	C21—H21C	0.9600
C6—C7	1.417 (4)	C22—H22A	0.9600
C6—C10	1.424 (4)	C22—H22B	0.9600
C6—H6	0.9800	C22—H22C	0.9600
C7—C8	1.420 (4)
O1—Ni1—O1^i	179.999 (2)	C4—C5—Fe1	70.42 (18)
N1—Ni1—O1	93.47 (8)	C1—C5—Fe1	69.14 (19)
O1^i—Ni1—N1	86.53 (8)	C4—C5—H5	126.2
O1—Ni1—N1^i	86.53 (8)	C1—C5—H5	126.2
O1^i—Ni1—N1^i	93.47 (8)	Fe1—C5—H5	126.2
N1—Ni1—N1^i	180.00 (11)	C7—C6—C10	108.5 (2)
C1—Fe1—C9	123.82 (14)	C7—C6—Fe1	70.25 (16)
C1—Fe1—C2	40.67 (15)	C10—C6—Fe1	69.49 (15)
C9—Fe1—C2	160.93 (14)	C7—C6—H6	125.8
C1—Fe1—C5	40.91 (14)	C10—C6—H6	125.8
C9—Fe1—C5	106.68 (14)	Fe1—C6—H6	125.8
C2—Fe1—C5	68.60 (16)	C6—C7—C8	108.1 (3)
C1—Fe1—C10	105.98 (13)	C6—C7—Fe1	69.30 (16)
C9—Fe1—C10	41.49 (10)	C8—C7—Fe1	69.45 (17)
C2—Fe1—C10	123.52 (12)	C6—C7—H7	125.9
C5—Fe1—C10	119.95 (13)	C8—C7—H7	125.9
C1—Fe1—C6	120.27 (13)	Fe1—C7—H7	125.9
C9—Fe1—C6	68.90 (12)	C9—C8—C7	108.3 (2)
C2—Fe1—C6	107.31 (13)	C9—C8—Fe1	69.01 (15)
C5—Fe1—C6	155.59 (13)	C7—C8—Fe1	70.05 (16)
C10—Fe1—C6	40.82 (11)	C9—C8—H8	125.9
C1—Fe1—C8	161.23 (15)	C7—C8—H8	125.9
C9—Fe1—C8	40.51 (11)	Fe1—C8—H8	125.9
C2—Fe1—C8	157.13 (15)	C8—C9—C10	108.1 (2)
C5—Fe1—C8	124.80 (14)	C8—C9—Fe1	70.48 (15)
C10—Fe1—C8	68.80 (11)	C10—C9—Fe1	69.71 (14)
C6—Fe1—C8	68.33 (12)	C8—C9—H9	125.9
C1—Fe1—C3	67.92 (15)	C10—C9—H9	125.9
C9—Fe1—C3	156.97 (12)	Fe1—C9—H9	125.9
C2—Fe1—C3	40.19 (14)	C6—C10—C9	107.0 (2)
C5—Fe1—C3	68.15 (15)	C6—C10—C11	126.1 (2)
C10—Fe1—C3	160.87 (13)	C9—C10—C11	126.9 (2)
C6—Fe1—C3	125.19 (13)	C6—C10—Fe1	69.69 (15)
C8—Fe1—C3	122.72 (13)	C9—C10—Fe1	68.80 (14)
C1—Fe1—C4	68.08 (14)	C11—C10—Fe1	125.41 (17)
C9—Fe1—C4	121.06 (13)	O1—C11—C10	116.4 (2)
C2—Fe1—C4	68.09 (14)	O1—C11—C12	124.4 (2)
C5—Fe1—C4	40.32 (13)	C10—C11—C12	119.2 (2)
C10—Fe1—C4	155.94 (12)	C11—C12—C13	124.9 (2)
C6—Fe1—C4	162.46 (12)	C11—C12—H12	117.6
C8—Fe1—C4	108.91 (13)	C13—C12—H12	117.6
C3—Fe1—C4	40.54 (13)	N1—C13—C12	123.7 (2)
C1—Fe1—C7	156.10 (15)	N1—C13—C14	120.6 (2)
C9—Fe1—C7	68.37 (13)	C12—C13—C14	115.7 (2)
C2—Fe1—C7	121.67 (15)	C13—C14—H14A	109.5
C5—Fe1—C7	162.15 (13)	C13—C14—H14B	109.5
C10—Fe1—C7	68.50 (11)	H14A—C14—H14B	109.5
C6—Fe1—C7	40.45 (11)	C13—C14—H14C	109.5
C8—Fe1—C7	40.50 (12)	H14A—C14—H14C	109.5
C3—Fe1—C7	109.29 (14)	H14B—C14—H14C	109.5
C4—Fe1—C7	126.30 (12)	C20—C15—C16	121.4 (2)
C11—O1—Ni1	128.62 (16)	C20—C15—N1	119.2 (2)
C13—N1—Ni1	124.74 (18)	C16—C15—N1	119.3 (2)
C15—N1—Ni1	120.81 (16)	C17—C16—C15	118.3 (3)
C13—N1—C15	114.5 (2)	C17—C16—C22	121.0 (3)
C2—C1—C5	108.2 (3)	C15—C16—C22	120.7 (2)
C2—C1—Fe1	69.96 (19)	C18—C17—C16	121.0 (3)
C5—C1—Fe1	69.95 (18)	C18—C17—H17	119.5
C2—C1—H1	125.9	C16—C17—H17	119.5
C5—C1—H1	125.9	C19—C18—C17	120.1 (3)
Fe1—C1—H1	125.9	C19—C18—H18	119.9
C3—C2—C1	108.0 (3)	C17—C18—H18	119.9
C3—C2—Fe1	70.57 (17)	C18—C19—C20	121.2 (3)
C1—C2—Fe1	69.37 (18)	C18—C19—H19	119.4
C3—C2—H2	126.0	C20—C19—H19	119.4
C1—C2—H2	126.0	C15—C20—C19	117.9 (3)
Fe1—C2—H2	126.0	C15—C20—C21	121.5 (3)
C2—C3—C4	108.1 (3)	C19—C20—C21	120.6 (3)
C2—C3—Fe1	69.24 (17)	C20—C21—H21A	109.5
C4—C3—Fe1	69.76 (17)	C20—C21—H21B	109.5
C2—C3—H3	125.9	H21A—C21—H21B	109.5
C4—C3—H3	125.9	C20—C21—H21C	109.5
Fe1—C3—H3	125.9	H21A—C21—H21C	109.5
C5—C4—C3	108.0 (3)	H21B—C21—H21C	109.5
C5—C4—Fe1	69.26 (18)	C16—C22—H22A	109.5
C3—C4—Fe1	69.69 (17)	C16—C22—H22B	109.5
C5—C4—H4	126.0	H22A—C22—H22B	109.5
C3—C4—H4	126.0	C16—C22—H22C	109.5
Fe1—C4—H4	126.0	H22A—C22—H22C	109.5
C4—C5—C1	107.6 (3)	H22B—C22—H22C	109.5
N1—Ni1—O1—C11	4.3 (2)	C2—Fe1—C7—C6	−79.4 (2)
N1^i—Ni1—O1—C11	−175.7 (2)	C5—Fe1—C7—C6	159.5 (4)
O1—Ni1—N1—C13	−4.5 (2)	C10—Fe1—C7—C6	37.66 (16)
O1^i—Ni1—N1—C13	175.5 (2)	C8—Fe1—C7—C6	119.8 (2)
O1—Ni1—N1—C15	175.95 (19)	C3—Fe1—C7—C6	−122.05 (18)
O1^i—Ni1—N1—C15	−4.05 (19)	C4—Fe1—C7—C6	−164.15 (18)
C9—Fe1—C1—C2	−164.99 (18)	C1—Fe1—C7—C8	−163.0 (3)
C5—Fe1—C1—C2	119.2 (3)	C9—Fe1—C7—C8	−37.35 (16)
C10—Fe1—C1—C2	−123.2 (2)	C2—Fe1—C7—C8	160.85 (18)
C6—Fe1—C1—C2	−81.3 (2)	C5—Fe1—C7—C8	39.7 (5)
C8—Fe1—C1—C2	165.8 (3)	C10—Fe1—C7—C8	−82.12 (17)
C3—Fe1—C1—C2	37.6 (2)	C6—Fe1—C7—C8	−119.8 (2)
C4—Fe1—C1—C2	81.4 (2)	C3—Fe1—C7—C8	118.17 (18)
C7—Fe1—C1—C2	−50.4 (4)	C4—Fe1—C7—C8	76.1 (2)
C9—Fe1—C1—C5	75.8 (2)	C6—C7—C8—C9	−0.1 (3)
C2—Fe1—C1—C5	−119.2 (3)	Fe1—C7—C8—C9	58.59 (19)
C10—Fe1—C1—C5	117.6 (2)	C6—C7—C8—Fe1	−58.68 (19)
C6—Fe1—C1—C5	159.45 (19)	C1—Fe1—C8—C9	38.6 (5)
C8—Fe1—C1—C5	46.6 (5)	C2—Fe1—C8—C9	−165.7 (3)
C3—Fe1—C1—C5	−81.7 (2)	C5—Fe1—C8—C9	74.0 (2)
C4—Fe1—C1—C5	−37.8 (2)	C10—Fe1—C8—C9	−38.47 (17)
C7—Fe1—C1—C5	−169.6 (3)	C6—Fe1—C8—C9	−82.47 (18)
C5—C1—C2—C3	−0.5 (4)	C3—Fe1—C8—C9	158.74 (18)
Fe1—C1—C2—C3	−60.2 (2)	C4—Fe1—C8—C9	116.01 (19)
C5—C1—C2—Fe1	59.7 (2)	C7—Fe1—C8—C9	−119.8 (2)
C1—Fe1—C2—C3	118.9 (3)	C1—Fe1—C8—C7	158.4 (4)
C9—Fe1—C2—C3	160.1 (4)	C9—Fe1—C8—C7	119.8 (2)
C5—Fe1—C2—C3	81.0 (2)	C2—Fe1—C8—C7	−45.9 (4)
C10—Fe1—C2—C3	−166.4 (2)	C5—Fe1—C8—C7	−166.21 (17)
C6—Fe1—C2—C3	−124.5 (2)	C10—Fe1—C8—C7	81.30 (17)
C8—Fe1—C2—C3	−49.3 (4)	C6—Fe1—C8—C7	37.30 (16)
C4—Fe1—C2—C3	37.5 (2)	C3—Fe1—C8—C7	−81.5 (2)
C7—Fe1—C2—C3	−82.6 (2)	C4—Fe1—C8—C7	−124.23 (18)
C9—Fe1—C2—C1	41.2 (5)	C7—C8—C9—C10	0.5 (3)
C5—Fe1—C2—C1	−37.9 (2)	Fe1—C8—C9—C10	59.79 (18)
C10—Fe1—C2—C1	74.7 (2)	C7—C8—C9—Fe1	−59.2 (2)
C6—Fe1—C2—C1	116.6 (2)	C1—Fe1—C9—C8	−166.01 (19)
C8—Fe1—C2—C1	−168.3 (3)	C2—Fe1—C9—C8	162.9 (4)
C3—Fe1—C2—C1	−118.9 (3)	C5—Fe1—C9—C8	−124.49 (19)
C4—Fe1—C2—C1	−81.4 (2)	C10—Fe1—C9—C8	118.9 (2)
C7—Fe1—C2—C1	158.5 (2)	C6—Fe1—C9—C8	80.92 (18)
C1—C2—C3—C4	0.4 (3)	C3—Fe1—C9—C8	−51.2 (4)
Fe1—C2—C3—C4	−59.1 (2)	C4—Fe1—C9—C8	−83.0 (2)
C1—C2—C3—Fe1	59.5 (2)	C7—Fe1—C9—C8	37.34 (17)
C1—Fe1—C3—C2	−38.0 (2)	C1—Fe1—C9—C10	75.1 (2)
C9—Fe1—C3—C2	−163.5 (3)	C2—Fe1—C9—C10	44.0 (5)
C5—Fe1—C3—C2	−82.3 (2)	C5—Fe1—C9—C10	116.61 (17)
C10—Fe1—C3—C2	36.8 (5)	C6—Fe1—C9—C10	−37.98 (16)
C6—Fe1—C3—C2	74.3 (3)	C8—Fe1—C9—C10	−118.9 (2)
C8—Fe1—C3—C2	159.5 (2)	C3—Fe1—C9—C10	−170.1 (3)
C4—Fe1—C3—C2	−119.6 (3)	C4—Fe1—C9—C10	158.13 (17)
C7—Fe1—C3—C2	116.6 (2)	C7—Fe1—C9—C10	−81.56 (17)
C1—Fe1—C3—C4	81.6 (2)	C7—C6—C10—C9	0.7 (3)
C9—Fe1—C3—C4	−43.9 (4)	Fe1—C6—C10—C9	−58.91 (18)
C2—Fe1—C3—C4	119.6 (3)	C7—C6—C10—C11	179.3 (2)
C5—Fe1—C3—C4	37.4 (2)	Fe1—C6—C10—C11	119.6 (2)
C10—Fe1—C3—C4	156.4 (3)	C7—C6—C10—Fe1	59.65 (19)
C6—Fe1—C3—C4	−166.06 (18)	C8—C9—C10—C6	−0.8 (3)
C8—Fe1—C3—C4	−80.9 (2)	Fe1—C9—C10—C6	59.47 (18)
C7—Fe1—C3—C4	−123.8 (2)	C8—C9—C10—C11	−179.3 (2)
C2—C3—C4—C5	−0.1 (4)	Fe1—C9—C10—C11	−119.1 (3)
Fe1—C3—C4—C5	−58.8 (2)	C8—C9—C10—Fe1	−60.27 (19)
C2—C3—C4—Fe1	58.8 (2)	C1—Fe1—C10—C6	118.08 (19)
C1—Fe1—C4—C5	38.3 (2)	C9—Fe1—C10—C6	−118.6 (2)
C9—Fe1—C4—C5	−78.9 (2)	C2—Fe1—C10—C6	77.2 (2)
C2—Fe1—C4—C5	82.3 (2)	C5—Fe1—C10—C6	160.16 (17)
C10—Fe1—C4—C5	−41.7 (4)	C8—Fe1—C10—C6	−80.97 (17)
C6—Fe1—C4—C5	160.3 (4)	C3—Fe1—C10—C6	49.6 (4)
C8—Fe1—C4—C5	−121.9 (2)	C4—Fe1—C10—C6	−170.1 (3)
C3—Fe1—C4—C5	119.5 (3)	C7—Fe1—C10—C6	−37.34 (16)
C7—Fe1—C4—C5	−163.7 (2)	C1—Fe1—C10—C9	−123.37 (19)
C1—Fe1—C4—C3	−81.2 (2)	C2—Fe1—C10—C9	−164.2 (2)
C9—Fe1—C4—C3	161.55 (19)	C5—Fe1—C10—C9	−81.3 (2)
C2—Fe1—C4—C3	−37.2 (2)	C6—Fe1—C10—C9	118.6 (2)
C5—Fe1—C4—C3	−119.5 (3)	C8—Fe1—C10—C9	37.59 (17)
C10—Fe1—C4—C3	−161.2 (3)	C3—Fe1—C10—C9	168.2 (4)
C6—Fe1—C4—C3	40.8 (5)	C4—Fe1—C10—C9	−51.5 (3)
C8—Fe1—C4—C3	118.6 (2)	C7—Fe1—C10—C9	81.22 (18)
C7—Fe1—C4—C3	76.8 (2)	C1—Fe1—C10—C11	−2.5 (3)
C3—C4—C5—C1	−0.3 (4)	C9—Fe1—C10—C11	120.9 (3)
Fe1—C4—C5—C1	−59.4 (2)	C2—Fe1—C10—C11	−43.3 (3)
C3—C4—C5—Fe1	59.1 (2)	C5—Fe1—C10—C11	39.6 (3)
C2—C1—C5—C4	0.5 (4)	C6—Fe1—C10—C11	−120.5 (3)
Fe1—C1—C5—C4	60.2 (2)	C8—Fe1—C10—C11	158.5 (3)
C2—C1—C5—Fe1	−59.7 (2)	C3—Fe1—C10—C11	−70.9 (5)
C1—Fe1—C5—C4	−118.6 (3)	C4—Fe1—C10—C11	69.4 (4)
C9—Fe1—C5—C4	118.6 (2)	C7—Fe1—C10—C11	−157.9 (3)
C2—Fe1—C5—C4	−80.9 (2)	Ni1—O1—C11—C12	−2.2 (4)
C10—Fe1—C5—C4	161.76 (18)	Ni1—O1—C11—C10	176.78 (16)
C6—Fe1—C5—C4	−165.8 (3)	C6—C10—C11—O1	−5.2 (4)
C8—Fe1—C5—C4	77.9 (2)	C9—C10—C11—O1	173.1 (2)
C3—Fe1—C5—C4	−37.6 (2)	Fe1—C10—C11—O1	84.3 (3)
C7—Fe1—C5—C4	47.6 (5)	C6—C10—C11—C12	173.8 (3)
C9—Fe1—C5—C1	−122.8 (2)	C9—C10—C11—C12	−7.9 (4)
C2—Fe1—C5—C1	37.7 (2)	Fe1—C10—C11—C12	−96.6 (3)
C10—Fe1—C5—C1	−79.6 (2)	O1—C11—C12—C13	−1.2 (4)
C6—Fe1—C5—C1	−47.2 (4)	C10—C11—C12—C13	179.8 (3)
C8—Fe1—C5—C1	−163.5 (2)	C15—N1—C13—C12	−177.5 (2)
C3—Fe1—C5—C1	81.0 (2)	Ni1—N1—C13—C12	2.9 (4)
C4—Fe1—C5—C1	118.6 (3)	C15—N1—C13—C14	1.8 (4)
C7—Fe1—C5—C1	166.2 (4)	Ni1—N1—C13—C14	−177.7 (2)
C1—Fe1—C6—C7	161.3 (2)	C11—C12—C13—N1	0.7 (5)
C9—Fe1—C6—C7	−80.99 (18)	C11—C12—C13—C14	−178.7 (3)
C2—Fe1—C6—C7	118.8 (2)	C13—N1—C15—C20	90.5 (3)
C5—Fe1—C6—C7	−164.9 (3)	Ni1—N1—C15—C20	−89.9 (3)
C10—Fe1—C6—C7	−119.6 (2)	C13—N1—C15—C16	−85.9 (3)
C8—Fe1—C6—C7	−37.34 (17)	Ni1—N1—C15—C16	93.7 (3)
C3—Fe1—C6—C7	78.2 (2)	C20—C15—C16—C17	−3.1 (4)
C4—Fe1—C6—C7	46.9 (5)	N1—C15—C16—C17	173.3 (2)
C1—Fe1—C6—C10	−79.2 (2)	C20—C15—C16—C22	177.2 (3)
C9—Fe1—C6—C10	38.59 (15)	N1—C15—C16—C22	−6.5 (4)
C2—Fe1—C6—C10	−121.60 (18)	C15—C16—C17—C18	1.3 (4)
C5—Fe1—C6—C10	−45.4 (4)	C22—C16—C17—C18	−179.0 (3)
C8—Fe1—C6—C10	82.24 (17)	C16—C17—C18—C19	0.9 (5)
C3—Fe1—C6—C10	−162.20 (17)	C17—C18—C19—C20	−1.3 (5)
C4—Fe1—C6—C10	166.5 (4)	C16—C15—C20—C19	2.7 (4)
C7—Fe1—C6—C10	119.6 (2)	N1—C15—C20—C19	−173.7 (2)
C10—C6—C7—C8	−0.4 (3)	C16—C15—C20—C21	−178.2 (3)
Fe1—C6—C7—C8	58.8 (2)	N1—C15—C20—C21	5.5 (4)
C10—C6—C7—Fe1	−59.18 (18)	C18—C19—C20—C15	−0.5 (4)
C1—Fe1—C7—C6	−43.2 (4)	C18—C19—C20—C21	−179.6 (3)
C9—Fe1—C7—C6	82.44 (18)

Symmetry code: (i) −x+1, −y+1, −z+1.