(2-Chloro-pyrimidin-4-yl)ferrocene.

In the title compound, [Fe(C5H5)(C9H6ClN2)], the two cyclo-penta-dienyl rings are almost parallel, subtending a dihedral angle of 3.01 (5)°. The dihedral angle between the substituted cyclo-penta-dienyl ring and the pyrimidinyl ring is 12.02 (1)°. The conformation of the two cyclopentadienyl rings in the ferrocenyl moiety is eclipsed.

Related literature

For pyrimidinyl derivatives, see: Chinchilla et al. (2004 ▶); Walker et al. (2009 ▶). For ferrocenyl pyrimidines, see: Xu et al. (2009 ▶, 2010 ▶). For the synthesis of the title compound, see: Xu et al. (2014 ▶).

Experimental

Crystal data

[Fe(C5H5)(C9H6ClN2)]

M = 298.55

Monoclinic,

a = 10.5064 (18) Å

b = 10.2684 (17) Å

c = 11.843 (2) Å

β = 108.580 (2)°

V = 1211.1 (4) Å3

Z = 4

Mo Kα radiation

μ = 1.45 mm−1

T = 296 K

0.43 × 0.15 × 0.12 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2004 ▶) T min = 0.575, T max = 0.846

8932 measured reflections

2251 independent reflections

1777 reflections with I > 2σ(I)

R int = 0.034

Refinement

R[F 2 > 2σ(F 2)] = 0.032

wR(F 2) = 0.111

S = 0.73

2251 reflections

163 parameters

H-atom parameters constrained

Δρmax = 0.28 e Å−3

Δρmin = −0.23 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536814004917/fj2665sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814004917/fj2665Isup2.hkl

CCDC reference: 989734

Additional supporting information: crystallographic information; 3D view; checkCIF report

[Fe(C5H5)(C9H6ClN2)]	F(000) = 608
Mr = 298.55	Dx = 1.637 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2413 reflections
a = 10.5064 (18) Å	θ = 2.7–24.7°
b = 10.2684 (17) Å	µ = 1.45 mm−1
c = 11.843 (2) Å	T = 296 K
β = 108.580 (2)°	Block, red
V = 1211.1 (4) Å3	0.43 × 0.15 × 0.12 mm
Z = 4

Bruker SMART APEX CCD area-detector diffractometer	2251 independent reflections
Radiation source: fine-focus sealed tube	1777 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.034
phi and ω scans	θmax = 25.5°, θmin = 2.7°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −12→12
Tmin = 0.575, Tmax = 0.846	k = −12→12
8932 measured reflections	l = −14→14

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.032	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.111	H-atom parameters constrained
S = 0.73	w = 1/[σ2(Fo2) + (0.1P)2 + 1.P] where P = (Fo2 + 2Fc2)/3
2251 reflections	(Δ/σ)max = 0.001
163 parameters	Δρmax = 0.28 e Å−3
0 restraints	Δρmin = −0.23 e Å−3

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 takeninto account individually in the estimation of e.s.d.'s in distances, anglesand torsion angles; correlations between e.s.d.'s in cell parameters are onlyused 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.

	x	y	z	Uiso*/Ueq
Fe1	0.83734 (4)	0.37324 (4)	0.13102 (3)	0.03675 (17)
Cl1	0.30992 (10)	0.08466 (10)	0.06208 (8)	0.0682 (3)
N1	0.4864 (2)	0.2434 (2)	0.0285 (2)	0.0417 (6)
N2	0.3649 (3)	0.1085 (3)	−0.1350 (2)	0.0508 (7)
C1	0.6492 (3)	0.4015 (3)	0.0148 (3)	0.0385 (6)
C2	0.6641 (3)	0.4632 (3)	0.1266 (3)	0.0437 (7)
H2	0.6107	0.4447	0.1791	0.052*
C3	0.7683 (3)	0.5561 (3)	0.1477 (3)	0.0493 (8)
H3	0.8004	0.6120	0.2182	0.059*
C4	0.8204 (3)	0.5527 (3)	0.0520 (3)	0.0489 (8)
H4	0.8948	0.6057	0.0444	0.059*
C5	0.7475 (3)	0.4585 (3)	−0.0309 (3)	0.0419 (7)
H5	0.7626	0.4353	−0.1059	0.050*
C6	0.8598 (4)	0.1813 (3)	0.1773 (4)	0.0639 (10)
H6	0.7911	0.1132	0.1529	0.077*
C7	0.9520 (5)	0.2188 (5)	0.1171 (4)	0.0812 (14)
H7	0.9582	0.1812	0.0430	0.097*
C8	1.0339 (4)	0.3189 (5)	0.1849 (4)	0.0733 (12)
H8	1.1066	0.3637	0.1654	0.088*
C9	0.9945 (4)	0.3419 (4)	0.2828 (3)	0.0655 (11)
H9	1.0339	0.4064	0.3451	0.079*
C10	0.8885 (4)	0.2581 (4)	0.2782 (3)	0.0583 (9)
H10	0.8409	0.2548	0.3372	0.070*
C11	0.5533 (3)	0.2986 (3)	−0.0397 (2)	0.0389 (6)
C12	0.5267 (3)	0.2604 (3)	−0.1578 (3)	0.0457 (7)
H12	0.5714	0.2980	−0.2059	0.055*
C13	0.4320 (3)	0.1651 (3)	−0.2007 (3)	0.0511 (8)
H13	0.4136	0.1385	−0.2793	0.061*
C14	0.3983 (3)	0.1538 (3)	−0.0259 (3)	0.0464 (7)

	U11	U22	U33	U12	U13	U23
Fe1	0.0331 (3)	0.0351 (3)	0.0377 (3)	−0.00076 (15)	0.00512 (18)	0.00464 (15)
Cl1	0.0639 (6)	0.0770 (6)	0.0607 (6)	−0.0252 (5)	0.0156 (4)	0.0025 (5)
N1	0.0371 (12)	0.0417 (13)	0.0414 (13)	0.0004 (10)	0.0053 (10)	−0.0030 (10)
N2	0.0431 (15)	0.0503 (15)	0.0523 (16)	−0.0046 (11)	0.0059 (13)	−0.0119 (12)
C1	0.0355 (15)	0.0343 (13)	0.0390 (15)	0.0042 (11)	0.0024 (12)	0.0005 (11)
C2	0.0378 (15)	0.0423 (16)	0.0481 (16)	0.0026 (13)	0.0095 (13)	−0.0074 (13)
C3	0.0484 (18)	0.0362 (15)	0.0559 (18)	−0.0029 (13)	0.0063 (15)	−0.0104 (13)
C4	0.0500 (18)	0.0353 (15)	0.0556 (19)	−0.0059 (13)	0.0088 (15)	0.0069 (13)
C5	0.0450 (16)	0.0376 (15)	0.0387 (14)	0.0016 (13)	0.0074 (12)	0.0071 (12)
C6	0.062 (2)	0.0346 (17)	0.075 (2)	0.0047 (15)	−0.0064 (19)	0.0087 (16)
C7	0.099 (3)	0.087 (3)	0.055 (2)	0.062 (3)	0.021 (2)	0.015 (2)
C8	0.0395 (19)	0.086 (3)	0.090 (3)	0.0114 (19)	0.0146 (19)	0.040 (3)
C9	0.057 (2)	0.057 (2)	0.060 (2)	−0.0097 (17)	−0.0145 (18)	0.0175 (17)
C10	0.062 (2)	0.059 (2)	0.0475 (18)	−0.0065 (16)	0.0076 (16)	0.0178 (16)
C11	0.0343 (14)	0.0360 (14)	0.0399 (15)	0.0084 (11)	0.0027 (12)	0.0004 (11)
C12	0.0400 (16)	0.0533 (18)	0.0403 (16)	−0.0010 (13)	0.0081 (13)	−0.0074 (13)
C13	0.0447 (18)	0.0585 (19)	0.0440 (17)	0.0015 (15)	0.0056 (14)	−0.0140 (15)
C14	0.0396 (16)	0.0430 (16)	0.0508 (18)	−0.0013 (13)	0.0064 (14)	0.0020 (13)

Fe1—C2	2.027 (3)	C3—C4	1.408 (5)
Fe1—C7	2.029 (4)	C3—H3	0.9800
Fe1—C10	2.032 (3)	C4—C5	1.416 (4)
Fe1—C8	2.036 (4)	C4—H4	0.9800
Fe1—C1	2.038 (3)	C5—H5	0.9800
Fe1—C6	2.040 (3)	C6—C10	1.383 (5)
Fe1—C9	2.042 (3)	C6—C7	1.426 (6)
Fe1—C3	2.045 (3)	C6—H6	0.9800
Fe1—C5	2.045 (3)	C7—C8	1.415 (6)
Fe1—C4	2.049 (3)	C7—H7	0.9800
Cl1—C14	1.751 (3)	C8—C9	1.370 (6)
N1—C14	1.319 (4)	C8—H8	0.9800
N1—C11	1.352 (4)	C9—C10	1.395 (5)
N2—C14	1.313 (4)	C9—H9	0.9800
N2—C13	1.337 (4)	C10—H10	0.9800
C1—C2	1.430 (4)	C11—C12	1.394 (4)
C1—C5	1.436 (4)	C12—C13	1.372 (4)
C1—C11	1.461 (4)	C12—H12	0.9300
C2—C3	1.413 (4)	C13—H13	0.9300
C2—H2	0.9800
C2—Fe1—C7	154.86 (19)	C4—C3—Fe1	70.02 (17)
C2—Fe1—C10	106.10 (15)	C2—C3—Fe1	69.01 (16)
C7—Fe1—C10	67.27 (16)	C4—C3—H3	125.7
C2—Fe1—C8	161.11 (18)	C2—C3—H3	125.7
C7—Fe1—C8	40.73 (19)	Fe1—C3—H3	125.7
C10—Fe1—C8	66.88 (16)	C3—C4—C5	108.2 (3)
C2—Fe1—C1	41.18 (12)	C3—C4—Fe1	69.75 (17)
C7—Fe1—C1	121.99 (16)	C5—C4—Fe1	69.62 (16)
C10—Fe1—C1	126.63 (14)	C3—C4—H4	125.9
C8—Fe1—C1	156.89 (17)	C5—C4—H4	125.9
C2—Fe1—C6	118.27 (15)	Fe1—C4—H4	125.9
C7—Fe1—C6	41.04 (17)	C4—C5—C1	108.2 (3)
C10—Fe1—C6	39.72 (15)	C4—C5—Fe1	69.89 (17)
C8—Fe1—C6	68.40 (16)	C1—C5—Fe1	69.14 (15)
C1—Fe1—C6	108.89 (13)	C4—C5—H5	125.9
C2—Fe1—C9	124.24 (16)	C1—C5—H5	125.9
C7—Fe1—C9	67.28 (18)	Fe1—C5—H5	125.9
C10—Fe1—C9	40.06 (15)	C10—C6—C7	106.4 (3)
C8—Fe1—C9	39.26 (17)	C10—C6—Fe1	69.84 (19)
C1—Fe1—C9	162.82 (16)	C7—C6—Fe1	69.1 (2)
C6—Fe1—C9	67.62 (15)	C10—C6—H6	126.8
C2—Fe1—C3	40.60 (12)	C7—C6—H6	126.8
C7—Fe1—C3	164.41 (19)	Fe1—C6—H6	126.8
C10—Fe1—C3	117.13 (15)	C8—C7—C6	107.5 (4)
C8—Fe1—C3	125.25 (17)	C8—C7—Fe1	69.9 (2)
C1—Fe1—C3	68.70 (12)	C6—C7—Fe1	69.9 (2)
C6—Fe1—C3	151.12 (16)	C8—C7—H7	126.3
C9—Fe1—C3	105.78 (15)	C6—C7—H7	126.3
C2—Fe1—C5	68.79 (13)	Fe1—C7—H7	126.3
C7—Fe1—C5	111.52 (14)	C9—C8—C7	108.2 (4)
C10—Fe1—C5	166.08 (13)	C9—C8—Fe1	70.6 (2)
C8—Fe1—C5	122.01 (15)	C7—C8—Fe1	69.4 (2)
C1—Fe1—C5	41.17 (12)	C9—C8—H8	125.9
C6—Fe1—C5	130.18 (14)	C7—C8—H8	125.9
C9—Fe1—C5	153.51 (14)	Fe1—C8—H8	125.9
C3—Fe1—C5	68.03 (12)	C8—C9—C10	108.3 (4)
C2—Fe1—C4	68.38 (13)	C8—C9—Fe1	70.1 (2)
C7—Fe1—C4	129.28 (17)	C10—C9—Fe1	69.58 (19)
C10—Fe1—C4	151.17 (14)	C8—C9—H9	125.9
C8—Fe1—C4	108.75 (15)	C10—C9—H9	125.9
C1—Fe1—C4	68.83 (12)	Fe1—C9—H9	125.9
C6—Fe1—C4	167.93 (16)	C6—C10—C9	109.7 (3)
C9—Fe1—C4	118.17 (14)	C6—C10—Fe1	70.44 (19)
C3—Fe1—C4	40.24 (13)	C9—C10—Fe1	70.36 (19)
C5—Fe1—C4	40.49 (12)	C6—C10—H10	125.2
C14—N1—C11	114.7 (3)	C9—C10—H10	125.2
C14—N2—C13	113.2 (3)	Fe1—C10—H10	125.2
C2—C1—C5	106.8 (3)	N1—C11—C12	120.4 (3)
C2—C1—C11	125.9 (3)	N1—C11—C1	117.1 (2)
C5—C1—C11	127.3 (3)	C12—C11—C1	122.5 (3)
C2—C1—Fe1	69.01 (16)	C13—C12—C11	117.5 (3)
C5—C1—Fe1	69.69 (16)	C13—C12—H12	121.2
C11—C1—Fe1	125.37 (19)	C11—C12—H12	121.2
C3—C2—C1	108.3 (3)	N2—C13—C12	123.3 (3)
C3—C2—Fe1	70.38 (17)	N2—C13—H13	118.3
C1—C2—Fe1	69.81 (16)	C12—C13—H13	118.3
C3—C2—H2	125.9	N2—C14—N1	130.9 (3)
C1—C2—H2	125.9	N2—C14—Cl1	114.6 (2)
Fe1—C2—H2	125.9	N1—C14—Cl1	114.5 (2)
C4—C3—C2	108.6 (3)
C7—Fe1—C1—C2	155.1 (2)	C8—Fe1—C6—C10	79.4 (3)
C10—Fe1—C1—C2	71.0 (2)	C1—Fe1—C6—C10	−125.1 (2)
C8—Fe1—C1—C2	−169.3 (4)	C9—Fe1—C6—C10	36.9 (2)
C6—Fe1—C1—C2	111.7 (2)	C3—Fe1—C6—C10	−45.2 (4)
C9—Fe1—C1—C2	36.5 (5)	C5—Fe1—C6—C10	−166.3 (2)
C3—Fe1—C1—C2	−37.63 (18)	C4—Fe1—C6—C10	157.9 (6)
C5—Fe1—C1—C2	−118.2 (2)	C2—Fe1—C6—C7	161.4 (2)
C4—Fe1—C1—C2	−80.94 (19)	C10—Fe1—C6—C7	−117.5 (3)
C2—Fe1—C1—C5	118.2 (2)	C8—Fe1—C6—C7	−38.1 (3)
C7—Fe1—C1—C5	−86.7 (2)	C1—Fe1—C6—C7	117.4 (2)
C10—Fe1—C1—C5	−170.79 (19)	C9—Fe1—C6—C7	−80.6 (3)
C8—Fe1—C1—C5	−51.1 (4)	C3—Fe1—C6—C7	−162.7 (3)
C6—Fe1—C1—C5	−130.1 (2)	C5—Fe1—C6—C7	76.2 (3)
C9—Fe1—C1—C5	154.7 (4)	C4—Fe1—C6—C7	40.4 (7)
C3—Fe1—C1—C5	80.55 (18)	C10—C6—C7—C8	−0.2 (4)
C4—Fe1—C1—C5	37.24 (17)	Fe1—C6—C7—C8	60.0 (2)
C2—Fe1—C1—C11	−119.8 (3)	C10—C6—C7—Fe1	−60.2 (2)
C7—Fe1—C1—C11	35.2 (3)	C2—Fe1—C7—C8	−159.8 (3)
C10—Fe1—C1—C11	−48.8 (3)	C10—Fe1—C7—C8	−80.4 (3)
C8—Fe1—C1—C11	70.9 (5)	C1—Fe1—C7—C8	159.5 (2)
C6—Fe1—C1—C11	−8.2 (3)	C6—Fe1—C7—C8	−118.4 (3)
C9—Fe1—C1—C11	−83.3 (5)	C9—Fe1—C7—C8	−36.9 (2)
C3—Fe1—C1—C11	−157.5 (3)	C3—Fe1—C7—C8	29.3 (7)
C5—Fe1—C1—C11	122.0 (3)	C5—Fe1—C7—C8	114.5 (2)
C4—Fe1—C1—C11	159.2 (3)	C4—Fe1—C7—C8	71.7 (3)
C5—C1—C2—C3	0.4 (3)	C2—Fe1—C7—C6	−41.4 (4)
C11—C1—C2—C3	179.3 (3)	C10—Fe1—C7—C6	37.9 (2)
Fe1—C1—C2—C3	60.1 (2)	C8—Fe1—C7—C6	118.4 (3)
C5—C1—C2—Fe1	−59.72 (19)	C1—Fe1—C7—C6	−82.2 (2)
C11—C1—C2—Fe1	119.2 (3)	C9—Fe1—C7—C6	81.5 (2)
C7—Fe1—C2—C3	−176.3 (3)	C3—Fe1—C7—C6	147.7 (5)
C10—Fe1—C2—C3	113.1 (2)	C5—Fe1—C7—C6	−127.1 (2)
C8—Fe1—C2—C3	47.9 (5)	C4—Fe1—C7—C6	−169.9 (2)
C1—Fe1—C2—C3	−119.1 (3)	C6—C7—C8—C9	0.2 (4)
C6—Fe1—C2—C3	154.2 (2)	Fe1—C7—C8—C9	60.2 (3)
C9—Fe1—C2—C3	73.2 (2)	C6—C7—C8—Fe1	−60.0 (2)
C5—Fe1—C2—C3	−80.56 (19)	C2—Fe1—C8—C9	34.0 (6)
C4—Fe1—C2—C3	−36.93 (18)	C7—Fe1—C8—C9	−119.1 (3)
C7—Fe1—C2—C1	−57.2 (4)	C10—Fe1—C8—C9	−37.6 (2)
C10—Fe1—C2—C1	−127.83 (19)	C1—Fe1—C8—C9	−168.3 (3)
C8—Fe1—C2—C1	167.0 (4)	C6—Fe1—C8—C9	−80.6 (3)
C6—Fe1—C2—C1	−86.8 (2)	C3—Fe1—C8—C9	70.2 (3)
C9—Fe1—C2—C1	−167.72 (18)	C5—Fe1—C8—C9	154.6 (2)
C3—Fe1—C2—C1	119.1 (3)	C4—Fe1—C8—C9	111.9 (2)
C5—Fe1—C2—C1	38.49 (17)	C2—Fe1—C8—C7	153.0 (4)
C4—Fe1—C2—C1	82.13 (18)	C10—Fe1—C8—C7	81.5 (3)
C1—C2—C3—C4	−0.8 (3)	C1—Fe1—C8—C7	−49.2 (5)
Fe1—C2—C3—C4	59.0 (2)	C6—Fe1—C8—C7	38.4 (2)
C1—C2—C3—Fe1	−59.8 (2)	C9—Fe1—C8—C7	119.1 (4)
C2—Fe1—C3—C4	−120.2 (3)	C3—Fe1—C8—C7	−170.7 (2)
C7—Fe1—C3—C4	53.9 (6)	C5—Fe1—C8—C7	−86.4 (3)
C10—Fe1—C3—C4	156.68 (19)	C4—Fe1—C8—C7	−129.1 (2)
C8—Fe1—C3—C4	76.9 (2)	C7—C8—C9—C10	−0.1 (4)
C1—Fe1—C3—C4	−81.99 (19)	Fe1—C8—C9—C10	59.3 (3)
C6—Fe1—C3—C4	−172.7 (3)	C7—C8—C9—Fe1	−59.5 (2)
C9—Fe1—C3—C4	115.2 (2)	C2—Fe1—C9—C8	−167.4 (2)
C5—Fe1—C3—C4	−37.55 (17)	C7—Fe1—C9—C8	38.2 (3)
C7—Fe1—C3—C2	174.1 (5)	C10—Fe1—C9—C8	119.4 (4)
C10—Fe1—C3—C2	−83.2 (2)	C1—Fe1—C9—C8	164.3 (4)
C8—Fe1—C3—C2	−162.9 (2)	C6—Fe1—C9—C8	82.8 (3)
C1—Fe1—C3—C2	38.16 (18)	C3—Fe1—C9—C8	−127.0 (3)
C6—Fe1—C3—C2	−52.6 (3)	C5—Fe1—C9—C8	−54.8 (4)
C9—Fe1—C3—C2	−124.7 (2)	C4—Fe1—C9—C8	−85.5 (3)
C5—Fe1—C3—C2	82.60 (19)	C2—Fe1—C9—C10	73.2 (3)
C4—Fe1—C3—C2	120.2 (3)	C7—Fe1—C9—C10	−81.2 (3)
C2—C3—C4—C5	0.8 (3)	C8—Fe1—C9—C10	−119.4 (4)
Fe1—C3—C4—C5	59.2 (2)	C1—Fe1—C9—C10	44.9 (6)
C2—C3—C4—Fe1	−58.4 (2)	C6—Fe1—C9—C10	−36.6 (2)
C2—Fe1—C4—C3	37.25 (17)	C3—Fe1—C9—C10	113.6 (2)
C7—Fe1—C4—C3	−163.7 (2)	C5—Fe1—C9—C10	−174.2 (3)
C10—Fe1—C4—C3	−46.9 (4)	C4—Fe1—C9—C10	155.1 (2)
C8—Fe1—C4—C3	−122.8 (2)	C7—C6—C10—C9	0.1 (4)
C1—Fe1—C4—C3	81.64 (19)	Fe1—C6—C10—C9	−59.6 (3)
C6—Fe1—C4—C3	162.9 (6)	C7—C6—C10—Fe1	59.7 (2)
C9—Fe1—C4—C3	−81.1 (2)	C8—C9—C10—C6	0.0 (4)
C5—Fe1—C4—C3	119.5 (3)	Fe1—C9—C10—C6	59.7 (2)
C2—Fe1—C4—C5	−82.23 (19)	C8—C9—C10—Fe1	−59.6 (3)
C7—Fe1—C4—C5	76.8 (3)	C2—Fe1—C10—C6	115.1 (2)
C10—Fe1—C4—C5	−166.4 (3)	C7—Fe1—C10—C6	−39.1 (3)
C8—Fe1—C4—C5	117.7 (2)	C8—Fe1—C10—C6	−83.5 (3)
C1—Fe1—C4—C5	−37.85 (18)	C1—Fe1—C10—C6	74.7 (3)
C6—Fe1—C4—C5	43.5 (7)	C9—Fe1—C10—C6	−120.4 (3)
C9—Fe1—C4—C5	159.5 (2)	C3—Fe1—C10—C6	157.4 (2)
C3—Fe1—C4—C5	−119.5 (3)	C5—Fe1—C10—C6	48.7 (7)
C3—C4—C5—C1	−0.6 (3)	C4—Fe1—C10—C6	−170.6 (3)
Fe1—C4—C5—C1	58.73 (19)	C2—Fe1—C10—C9	−124.5 (3)
C3—C4—C5—Fe1	−59.3 (2)	C7—Fe1—C10—C9	81.2 (3)
C2—C1—C5—C4	0.1 (3)	C8—Fe1—C10—C9	36.8 (3)
C11—C1—C5—C4	−178.8 (3)	C1—Fe1—C10—C9	−164.9 (2)
Fe1—C1—C5—C4	−59.2 (2)	C6—Fe1—C10—C9	120.4 (3)
C2—C1—C5—Fe1	59.28 (19)	C3—Fe1—C10—C9	−82.3 (3)
C11—C1—C5—Fe1	−119.6 (3)	C5—Fe1—C10—C9	169.1 (5)
C2—Fe1—C5—C4	81.1 (2)	C4—Fe1—C10—C9	−50.2 (4)
C7—Fe1—C5—C4	−125.9 (2)	C14—N1—C11—C12	0.3 (4)
C10—Fe1—C5—C4	151.9 (6)	C14—N1—C11—C1	178.1 (3)
C8—Fe1—C5—C4	−81.5 (3)	C2—C1—C11—N1	−10.2 (4)
C1—Fe1—C5—C4	119.6 (3)	C5—C1—C11—N1	168.4 (3)
C6—Fe1—C5—C4	−169.2 (2)	Fe1—C1—C11—N1	78.1 (3)
C9—Fe1—C5—C4	−43.9 (4)	C2—C1—C11—C12	167.5 (3)
C3—Fe1—C5—C4	37.33 (18)	C5—C1—C11—C12	−13.8 (4)
C2—Fe1—C5—C1	−38.51 (17)	Fe1—C1—C11—C12	−104.2 (3)
C7—Fe1—C5—C1	114.5 (2)	N1—C11—C12—C13	−0.6 (4)
C10—Fe1—C5—C1	32.2 (6)	C1—C11—C12—C13	−178.2 (3)
C8—Fe1—C5—C1	158.9 (2)	C14—N2—C13—C12	0.4 (5)
C6—Fe1—C5—C1	71.2 (2)	C11—C12—C13—N2	0.2 (5)
C9—Fe1—C5—C1	−163.6 (3)	C13—N2—C14—N1	−0.8 (5)
C3—Fe1—C5—C1	−82.32 (18)	C13—N2—C14—Cl1	178.7 (2)
C4—Fe1—C5—C1	−119.6 (3)	C11—N1—C14—N2	0.4 (5)
C2—Fe1—C6—C10	−81.1 (2)	C11—N1—C14—Cl1	−179.0 (2)
C7—Fe1—C6—C10	117.5 (3)